US 2011 0319437A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0319437 A1 TOH et al. (43) Pub. Date: Dec. 29, 2011

(54) IMINOPROPENE COMPOUND AND USE Publication Classification THEREOF (51) Int. Cl. AOIN 37/52 (2006.01) (75) Inventors: Shigeyuki ITOH, Osaka-shi (JP); C07D 213/65 (2006.01) Atsushi IWATA, Takarazuka-shi C07D 23/30 (2006.01) (JP) C07D 319/18 (2006.01) C07D 2.39/38 (2006.01) AOIP 7/02 (2006.01) (73) Assignee: SUMTOMO CHEMICAL AOIN 43/40 (2006.01) COMPANY., LIMITED, Tokyo AOIN 43/32 (2006.01) (JP) 9 s AOIN 43/54 (2006.01) AOIN 43/50 (2006.01) AOIP 7/04 (2006.01) C07C323/45 (2006.01) (21) Appl. No.: 13/222,512 C07D 277/36 (2006.01) (52) U.S. Cl...... 514/274; 558/1; 558/9: 546/292; 546/334; 549/362: 548/323.5; 548/186: 514/508; (22) Filed: Aug. 31, 2011 514/346; 514/357: 514/452: 514/398 (57) ABSTRACT Related U.S. Application Data The compound (I) or a salt thereof has an excellent control ling activity against pests. Then the compound (I) or a salt (60) Division of application No. 1 1/878,392, filed on Jul. thereof is useful for an active ingredient of a pesticidal com 24, 2007, which is a continuation-in-part of applica- position. tion No. PCT/JP2006/322698, filed on Nov. 8, 2006.

(I) (30) Foreign Application Priority Data Y Dec. 1, 2005 (JP) ...... 2005-347646 X-CHoCH-CEN-Z May 26, 2006 (JP) ...... 2006-146381 US 2011/0319437 A1 Dec. 29, 2011

IMINOPROPENE COMPOUND AND USE ally substituted, a heterocyclic group optionally Substituted, THEREOF C(—Q')X', C(=O)CX, C(-Q12)NXPXE, SOX, NXX or N. C(X), CROSS-REFERENCE TO RELATED I0012 X represents a lower alkyl group optionally substi APPLICATIONS tuted, a higher alkyl group, a lower cycloalkyl group option 0001. This is a divisional of U.S. application Ser. No. ally substituted, a lower alkenyl group optionally Substituted, 1 1/878.392 filed Jul. 24, 2007, which is a continuation-in-part a higher alkenyl group, a lower cycloalkenyl group optionally application of PCT/JP2006/322698, filed Nov. 8, 2006, Substituted, a lower alkynyl group optionally Substituted, a which claims priority to Japanese Application No. 2004-70, higher alkynyl group, an aromatic hydrocarbon group option ally substituted, a heterocyclic group optionally Substituted, 663 filed Mar. 12, 2004 and to Japanese Application No. C( Q?)X-12, C(=O)CX, C(-Q22)NXP2X2, SOX2, 2004-70,892 filed Mar. 12, 2004, the above-noted applica NX'X', N=C(X), OX' or a cyano group, tions incorporated herein by reference in their entirety. (0013 X represents a hydrogenatom, a lower alkyl group TECHNICAL FIELD optionally Substituted, a higher alkyl group, a lower cycloalkyl group optionally substituted, a lower alkenyl 0002 The present invention relates to an iminopropene group optionally substituted, a higher alkenyl group, a lower compound and pesticidal use thereof. cycloalkenyl group optionally Substituted, a lower alkynyl group optionally substituted, a higher alkynyl group, an aro BACKGROUND ART matic hydrocarbon group optionally Substituted, a heterocy 0003. Heretofore, the development of pesticides has been clic group optionally substituted, C(=Q')X", C(=O) carried out and many compounds which are effective for OX13, C(-Q2)NXD3XP3 O SOX, controlling pest have been found. However, their activity is (0014) alternatively, X and X represent a ring structure not always Sufficient. Accordingly, there are further demands together with the nitrogen which is bonded with each other, for developing novel compounds having pest-controlling I0015. X represents a lower alkyl group optionally substi activity. tuted, a higher alkyl group, a lower cycloalkyl group option ally substituted, a lower alkenyl group optionally Substituted, DISCLOSURE OF INVENTION a higher alkenyl group, a lower cycloalkenyl group optionally Substituted, a lower alkynyl group optionally Substituted, a 0004. The present invention is intended to provide a com higher alkynyl group, an aromatic hydrocarbon group option pound having Superior pest-controlling activity. ally substituted, a heterocyclic group optionally Substituted, 0005. The present inventor has intensively studied in order C( Q)X-1, C(O)OX, C( Q2)NXX* or S(O) to find a compound having Superior pest-controlling activity X4, and, as a result, has found that an iminopropene compound I0016 X represents a lower alkyl group optionally substi represented by the formula (I) has Superior pest-controlling tuted, a higher alkyl group, a lower cycloalkyl group option activity. Thus, the present invention has been completed. ally substituted, a lower alkenyl group optionally Substituted, 0006 That is, the present invention provides as follows: a higher alkenyl group, a lower cycloalkenyl group optionally 0007 An iminopropene compound given by the formula Substituted, a lower alkynyl group optionally Substituted, a (I) or a salt thereof: higher alkynyl group, an aromatic hydrocarbon group option ally Substituted oraheterocyclic group optionally Substituted, (I) I0017 X's represent each independently a lower alkyl Y group optionally Substituted, a higher alkyl group, a lower cycloalkyl group optionally substituted, a lower alkenyl X-CHCH-CEN-Z group optionally substituted, a higher alkenyl group, a lower cycloalkenyl group optionally Substituted, a lower alkynyl wherein, group optionally substituted, a higher alkynyl group, an aro 0008 X represents OX, NXX, SX, S(O),X, Si(X) matic hydrocarbon group optionally Substituted, a heterocy O N=C(X7), clic group optionally Substituted or a lower alkoxy group 0009 Y represents OY, NYY, SY., SOY or N=C optionally substituted, (Y), 10018. X's represent each independently a hydrogenatom, 0010 Z represents a cyano group, a lower alkyl group a lower alkyl group optionally Substituted, a higher alkyl optionally Substituted, a higher alkyl group, a lower group, a lower cycloalkyl group optionally Substituted, a cycloalkyl group optionally substituted, a lower alkenyl lower alkenyl group optionally Substituted, a higher alkenyl group optionally substituted, a higher alkenyl group, a lower group, a lower cycloalkenyl group optionally substituted, a cycloalkenyl group optionally Substituted, a lower alkynyl lower alkynyl group optionally Substituted, a higher alkynyl group optionally substituted, a higher alkynyl group, an aro group, an aromatic hydrocarbon group optionally Substituted, matic hydrocarbon group optionally Substituted, a heterocy a heterocyclic group optionally substituted, OX', SX' or clic group optionally substituted, C(=Q')Z", C(=O)CZ. NXG7XH7, C( Q2)NZZ, SOZ, NZZ, OZ^ or N. C(Z). 0019 alternatively, representaring structure together with I0011 X' represents a lower alkyl group optionally substi the carbon which is bonded with each other, tuted, a higher alkyl group, a lower cycloalkyl group option I0020 Y' represents a lower alkyl group optionally substi ally substituted, a lower alkenyl group optionally Substituted, tuted, a higher alkyl group, a lower cycloalkyl group option a higher alkenyl group, a lower cycloalkenyl group optionally ally substituted, a lower alkenyl group optionally Substituted, Substituted, a lower alkynyl group optionally Substituted, a a higher alkenyl group, a lower cycloalkenyl group optionally higher alkynyl group, an aromatic hydrocarbon group option Substituted, a lower alkynyl group optionally Substituted, a US 2011/0319437 A1 Dec. 29, 2011 higher alkynyl group, an aromatic hydrocarbon group option stituted, a higher alkynyl group, an aromatic hydrocarbon ally substituted, a heterocyclic group optionally Substituted, group optionally Substituted, a heterocyclic group optionally C( Q)Y', C(O)OY, C( Q52)NYPlyE, S(O).Y. Substituted or an amino group optionally substituted, or N=C(Y), 0029 XP, XP2, XP, XP, YP, Y-D2, YP3, YP4 and ZP I0021. Y' represents a lower alkyl group optionally substi represent each independently a hydrogen atom, a lower alkyl tuted, a higher alkyl group, a lower cycloalkyl group option group optionally Substituted, a higher alkyl group, a lower ally substituted, a lower alkenyl group optionally Substituted, cycloalkyl group optionally substituted, a lower alkenyl a higher alkenyl group, a lower cycloalkenyl group optionally group optionally substituted, a higher alkenyl group, a lower Substituted, a lower alkynyl group optionally Substituted, a cycloalkenyl group optionally Substituted, a lower alkynyl higher alkynyl group, an aromatic hydrocarbon group option group optionally substituted, a higher alkynyl group, an aro ally substituted, a heterocyclic group optionally Substituted, matic hydrocarbon group optionally Substituted, a heterocy C(-Q)Y12, C(O)OY, C( Q62)NYP2Y-2, SO.Y?, clic group optionally substituted, an amino group optionally NY'Y', N=C(Y'), OY^* or a cyano group, substituted, a cyano group or OG"', 0022 Y represents a hydrogenatom, a lower alkyl group 0030 and optionally Substituted, a higher alkyl group, a lower 0.031 XEl, XE2, XE3, XE4, YEl, YE2, YES, YE and ZF cycloalkyl group optionally substituted, a lower alkenyl represent each independently a hydrogen atom, a lower alkyl group optionally substituted, a higher alkenyl group, a lower group optionally Substituted, a higher alkyl group, a lower cycloalkenyl group optionally Substituted, a lower alkynyl cycloalkyl group optionally substituted, a lower alkenyl group optionally substituted, a higher alkynyl group, an aro group optionally substituted, a higher alkenyl group, a lower matic hydrocarbon group optionally Substituted, a heterocy cycloalkenyl group optionally Substituted, a lower alkynyl clic group optionally substituted, C(=Q7)Y', C(=O) group optionally substituted, a higher alkynyl group, an aro OYP3, C( Q72)NYPYE3 O SO.Y., matic hydrocarbon group optionally Substituted or a hetero 0023 Y' represents a lower alkyl group optionally substi cyclic group optionally Substituted, tuted, a higher alkyl group, a lower cycloalkyl group option 0032 alternatively, XP and X', XP and X, XP and ally substituted, a lower alkenyl group optionally Substituted, XP, XP and X-Y Pi and YE1, YP2 and YP, Y-D and Y-3, a higher alkenyl group, a lower cycloalkenyl group optionally YandY and ZP and Z representaring structure together Substituted, a lower alkynyl group optionally Substituted, a with the nitrogen which is bonded with each other, higher alkynyl group, an aromatic hydrocarbon group option 0033 X', X, X,Y',Y,Y and Z represent each ally substituted, a heterocyclic group optionally substituted, independently a lower alkyl group optionally substituted, a C(-QI)Y-1, C(-O)OY7, C(-Q82)NY Y- or S(O) higher alkyl group, a lower cycloalkyl group optionally Sub YF4. stituted, a lower alkenyl group optionally substituted, a higher foo24) Y represents a lower alkyl group optionally substi alkenyl group, a lower cycloalkenyl group optionally Substi tuted, a higher alkyl group, a lower cycloalkyl group option tuted, a lower alkynyl group optionally Substituted, a higher ally substituted, a lower alkenyl group optionally Substituted, alkynyl group, an aromatic hydrocarbon group optionally a higher alkenyl group, a lower cycloalkenyl group optionally Substituted, a heterocyclic group optionally Substituted or an Substituted, a lower alkynyl group optionally Substituted, a amino group optionally Substituted, higher alkynyl group, an aromatic hydrocarbon group option 0034 X and Y represent each independently a lower ally Substituted or a heterocyclic group optionally Substituted, alkyl group optionally Substituted, a higher alkyl group, a I0025 Y's represent each independently a hydrogenatom, lower cycloalkyl group optionally Substituted, a lower alk a lower alkyl group optionally Substituted, a higher alkyl enyl group optionally substituted, a higher alkenyl group, a group, a lower cycloalkyl group optionally Substituted, a lower cycloalkenyl group optionally Substituted, a lower lower alkenyl group optionally Substituted, a higher alkenyl alkynyl group optionally substituted, a higher alkynyl group, group, a lower cycloalkenyl group optionally substituted, a an aromatic hydrocarbon group optionally substituted or a lower alkynyl group optionally Substituted, a higher alkynyl heterocyclic group optionally Substituted, group, an aromatic hydrocarbon group optionally Substituted, 0035 X, X’, X7, Y', Y and Z represent each a heterocyclic group optionally substituted, OY, SY' or independently a hydrogen atom, a lower alkyl group option NY G6 H, ally Substituted, a higher alkyl group, a lower cycloalkyl 0026 alternatively, representaring structure together with group optionally Substituted, a lower alkenyl group option the carbon which is bonded with each other, ally Substituted, a higher alkenyl group, a lower cycloalkenyl 0027 X11, X42, X13, X44, Y41, Y42, Y43, Y- and Z. group optionally Substituted, a lower alkynyl group option represent each independently a lower alkyl group optionally ally Substituted, a higher alkynyl group, an aromatic hydro Substituted, a higher alkyl group, a lower cycloalkyl group carbon group optionally Substituted, a heterocyclic group optionally Substituted, a lower alkenyl group optionally Sub optionally substituted, C(=Q')G', C(=O)CG', stituted, a higher alkenyl group, a lower cycloalkenyl group C( Q?)NG'G' or SOG, optionally Substituted, a lower alkynyl group optionally Sub 0036 and stituted, a higher alkynyl group, an aromatic hydrocarbon 0037 X, X2, X7, Yi, Y and Z represent each group optionally Substituted or a heterocyclic group option independently a hydrogen atom, a lower alkyl group option ally substituted, ally Substituted, a higher alkyl group, a lower cycloalkyl 0028 X, X2, X53, X54, YBl, YB2, YB5, Y and Z group optionally Substituted, a lower alkenyl group option represent each independently a lower alkyl group optionally ally Substituted, a higher alkenyl group, a lower cycloalkenyl Substituted, a higher alkyl group, a lower cycloalkyl group group optionally Substituted, a lower alkynyl group option optionally Substituted, a lower alkenyl group optionally Sub ally Substituted, a higher alkynyl group, an aromatic hydro stituted, a higher alkenyl group, a lower cycloalkenyl group carbon group optionally substituted or a heterocyclic group optionally Substituted, a lower alkynyl group optionally Sub optionally substituted, US 2011/0319437 A1 Dec. 29, 2011

0038 alternatively, X and X', X’ and X', X7 and group, an aromatic hydrocarbon group optionally substituted, X-7, Y2 and Yi, Y and Y, and Z and Z represent a a heterocyclic group optionally substituted, an amino group ring structure together with the nitrogen which is bonded with optionally substituted, a cyano group or OG'. each other, 0047 and 0039 X, X, Y, Y- and Z represent each indepen 0048 G' and G' represent each independently a hydro dently a hydrogen atom, a lower alkyl group optionally Sub gen atom, a lower alkyl group optionally substituted, a higher stituted, a higher alkyl group, a lower cycloalkyl group alkyl group, a lower cycloalkyl group optionally substituted, optionally substituted, a lower alkenyl group optionally Sub a lower alkenyl group optionally substituted, a higher alkenyl stituted, a higher alkenyl group, a lower cycloalkenyl group group, a lower cycloalkenyl group optionally substituted, a optionally substituted, a lower alkynyl group optionally Sub lower alkynyl group optionally substituted, a higher alkynyl stituted, a higher alkynyl group, an aromatic hydrocarbon group, an aromatic hydrocarbon group optionally substituted group optionally substituted, a heterocyclic group optionally or a heterocyclic group optionally substituted, substituted, OG', SG" or NG'G' (0049) alternatively, G' and G', and G' and G' repre 0040 alternatively, representaring structure together with sent a ring structure together with the nitrogen which is the carbon which is bonded with each other, bonded with each other, 0041 X, Y and Z represent each independently a 0050 G' and G represent each independently a lower lower alkyl group optionally substituted, a higher alkyl group. alkyl group optionally substituted, a higher alkyl group, a a lower cycloalkyl group optionally substituted, a lower alk lower cycloalkyl group optionally substituted, a lower alk enyl group optionally substituted, a higher alkenyl group, a enyl group optionally substituted, a higher alkenyl group, a lower cycloalkenyl group optionally substituted, a lower lower cycloalkenyl group optionally substituted, a lower alkynyl group optionally substituted, a higher alkynyl group, alkynyl group optionally substituted, a higher alkynyl group. an aromatic hydrocarbon group optionally substituted, a het an aromatic hydrocarbon group optionally substituted, a het erocyclic group optionally substituted, C(=Q')G'. erocyclic group optionally substituted or an amino group C(-O)OG, C( Q^2)NG G2 or SOG, optionally substituted, 0042 X7, X, Y and Y' represent each indepen (0051) G' represents a hydrogen atom, a lower alkyl dently a hydrogen atom, a lower alkyl group optionally Sub group optionally substituted, a higher alkyl group, a lower stituted, a higher alkyl group, a lower cycloalkyl group cycloalkyl group optionally substituted, a lower alkenyl optionally substituted, a lower alkenyl group optionally Sub group optionally substituted, a higher alkenyl group, a lower stituted, a higher alkenyl group, a lower cycloalkenyl group cycloalkenyl group optionally substituted, a lower alkynyl optionally substituted, a lower alkynyl group optionally Sub group optionally substituted, a higher alkynyl group, an aro stituted, a higher alkynyl group, an aromatic hydrocarbon matic hydrocarbon group optionally substituted, a heterocy group optionally substituted or a heterocyclic group option clic group optionally substituted, C(=Q')G"', C(=O) ally substituted, OG'l-, C( Qob)NGP-GE-1 Or SOG'-', 0043 G', G' and G' represent each independently a 0052 and hydrogen atom, a lower alkyl group optionally substituted, a (0053 G' represents a hydrogen atom, a lower alkyl higher alkyl group, a lower cycloalkyl group optionally sub group optionally substituted, a higher alkyl group, a lower stituted, a lower alkenyl group optionally substituted, a higher cycloalkyl group optionally substituted, a lower alkenyl alkenyl group, a lower cycloalkenyl group optionally substi group optionally substituted, a higher alkenyl group, a lower tuted, a lower alkynyl group optionally substituted, a higher cycloalkenyl group optionally substituted, a lower alkynyl alkynyl group, an aromatic hydrocarbon group optionally group optionally substituted, a higher alkynyl group, an aro substituted or a heterocyclic group optionally substituted, matic hydrocarbon group optionally substituted or a hetero 0044) G' and G' represent each independently a lower cyclic group optionally substituted, alkyl group optionally substituted, a higher alkyl group, a 0054) alternatively, G' and G' representaring structure lower cycloalkyl group optionally substituted, a lower alk together with the nitrogen which is bonded with each other, enyl group optionally substituted, a higher alkenyl group, a (0055) G' represents a hydrogenatom, a lower alkyl group lower cycloalkenyl group optionally substituted, a lower optionally substituted, a higher alkyl group, a lower alkynyl group optionally substituted, a higher alkynyl group. cycloalkyl group optionally substituted, a lower alkenyl an aromatic hydrocarbon group optionally substituted or a group optionally substituted, a higher alkenyl group, a lower heterocyclic group optionally substituted, cycloalkenyl group optionally substituted, a lower alkynyl 0045 G' and G' represent each independently a lower group optionally substituted, a higher alkynyl group, an aro alkyl group optionally substituted, a higher alkyl group, a matic hydrocarbon group optionally substituted or a hetero lower cycloalkyl group optionally substituted, a lower alk cyclic group optionally substituted, enyl group optionally substituted, a higher alkenyl group, a 0056 G' represents a lower alkyl group optionally sub lower cycloalkenyl group optionally substituted, a lower stituted, a higher alkyl group, a lower cycloalkyl group alkynyl group optionally substituted, a higher alkynyl group. optionally substituted, a lower alkenyl group optionally Sub an aromatic hydrocarbon group optionally substituted, a het stituted, a higher alkenyl group, a lower cycloalkenyl group erocyclic group optionally substituted or an amino group optionally substituted, a lower alkynyl group optionally Sub optionally substituted, stituted, a higher alkynyl group, an aromatic hydrocarbon 10046) G' and G' represent eachindependently a hydro group optionally substituted or a heterocyclic group option gen atom, a lower alkyl group optionally substituted, a higher ally substituted, alkyl group, a lower cycloalkyl group optionally substituted, (0057 G' represents a lower alkyl group optionally sub a lower alkenyl group optionally substituted, a higher alkenyl stituted, a higher alkyl group, a lower cycloalkyl group group, a lower cycloalkenyl group optionally substituted, a optionally substituted, a lower alkenyl group optionally Sub lower alkynyl group optionally substituted, a higher alkynyl stituted, a higher alkenyl group, a lower cycloalkenyl group US 2011/0319437 A1 Dec. 29, 2011

optionally Substituted, a lower alkynyl group optionally Sub MODE OF CARRYING OUT THE INVENTION stituted, a higher alkynyl group, an aromatic hydrocarbon 0070 First, the embodiment of the compound (I) is exem group optionally Substituted, a heterocyclic group optionally plified as following 1 to 33. Substituted or an amino group optionally substituted, 1 An iminopropene compound given by the formula (I) or a I0058 G' represents a hydrogen atom, a lower alkyl salt thereof: group optionally substituted, a higher alkyl group, a lower cycloalkyl group optionally substituted, a lower alkenyl group optionally substituted, a higher alkenyl group, a lower (I) cycloalkenyl group optionally Substituted, a lower alkynyl Y group optionally substituted, a higher alkynyl group, an aro X-CHoCH-CEN-Z matic hydrocarbon group optionally Substituted, a heterocy clic group optionally substituted, an amino group optionally wherein, Substituted, a cyano group or OL, (0071 X, Y and Z are defined above. 0059 and 0072 Here, 1) if X is a benzoyloxy group and Y is a I0060 G''' represents a hydrogen atom, a lower alkyl methoxy group, then, Z is not a 2-(benzoylamino) vinyl group optionally substituted, a higher alkyl group, a lower grOup, cycloalkyl group optionally substituted, a lower alkenyl (0073. 2) if X is a methyl group, then, X is not a methyl group optionally substituted, a higher alkenyl group, a lower grOup, cycloalkenyl group optionally Substituted, a lower alkynyl 0074 3) if X is a methoxy group and Y is a trifluorometh group optionally substituted, a higher alkynyl group, an aro ylsulfonyloxy group, then, Z is not a 3-vinyloxypropyl group. 2 The compound according to 1, wherein matic hydrocarbon group optionally Substituted or a hetero (0075 X is OX', NXX, SX or S(O).X. cyclic group optionally Substituted, (wherein, X and X’ are a lower alkyl group optionally sub 0061 alternatively, G'' and G''' representaring struc stituted, a higher alkyl group, a lower cycloalkyl group ture together with the nitrogen which is bonded with each optionally Substituted, a lower alkenyl group optionally Sub other, stituted, a higher alkenyl group, a lower cycloalkenyl group I0062 G' represents a lower alkyl group optionally sub optionally Substituted, a lower alkynyl group optionally Sub Stituted, a higher alkyl group, a lower cycloalkyl group Stituted, a higher alkynyl group, an aromatic hydrocarbon optionally Substituted, a lower alkenyl group optionally Sub group optionally Substituted, a heterocyclic group optionally stituted, a higher alkenyl group, a lower cycloalkenyl group substituted, C(=Q')X' (wherein, Q is an oxygen atom, optionally Substituted, a lower alkynyl group optionally Sub and X" is a lower alkyl group optionally substituted), stituted, a higher alkynyl group, an aromatic hydrocarbon NXX or N CCX), group optionally Substituted, a heterocyclic group optionally (0076 X" and X are each independently a lower alkyl Substituted or an amino group optionally substituted, group optionally Substituted, a higher alkyl group, a lower cycloalkyl group optionally substituted, a lower alkenyl 0063 L represents a hydrogen atom, a lower alkyl group group optionally substituted, a higher alkenyl group, a lower optionally Substituted, a higher alkyl group, a lower cycloalkenyl group optionally Substituted, a lower alkynyl cycloalkyl group optionally substituted, a lower alkenyl group optionally substituted, a higher alkynyl group, an aro group optionally substituted, a higher alkenyl group, a lower matic hydrocarbon group optionally Substituted, a heterocy cycloalkenyl group optionally Substituted, a lower alkynyl clic group optionally substituted or C(=Q')X' (wherein, group optionally substituted, a higher alkynyl group, an aro Q'' is an oxygen atom, and X" is a lower alkyl group option matic hydrocarbon group optionally Substituted or a hetero ally substituted), cyclic group optionally Substituted, 10077 X is a hydrogen atom, a lower alkyl group option ally Substituted, a higher alkyl group, a lower cycloalkyl 99.8, 9.8883,333.3 group optionally Substituted, a lower alkenyl group option Q' and Q' represent each independently oxygen or sulfur, ally Substituted, a higher alkenyl group, a lower cycloalkenyl 0065 m represents an integer of 1 or 2, group optionally Substituted, a lower alkynyl group option 0.066 n., p and q represent eachindependently an integer of ally Substituted, a higher alkynyl group, an aromatic hydro 0 or 2, carbon group optionally substituted or a heterocyclic group 0067 here, 1) if X is a benzoyloxy group and Y is a optionally substituted, methoxy group, then, Z is not a 2-(benzoylamino) vinyl (0078 alternatively, X and X are formed a ring structure together with the nitrogen which is bonded with each other), grOup, 0079 Y is OY, NY2Y or SY I0068. 2) if X is a methyl group, then, X is not a methyl (wherein, Y is a lower alkyl group optionally substituted, a grOup, higher alkyl group, a lower cycloalkyl group optionally Sub 0069. 3) if X is a methoxy group and Y is a trifluorometh stituted, a lower alkenyl group optionally substituted, a higher ylsulfonyloxy group, then, Z is not a 3-vinyloxypropyl group alkenyl group, a lower cycloalkenyl group optionally Substi (referred as the compound (I), hereinafter); tuted, a lower alkynyl group optionally Substituted, a higher a pesticidal composition comprising the compound (I) or a alkynyl group, an aromatic hydrocarbon group optionally salt thereof as an active ingredient and an inert carrier; and Substituted, a heterocyclic group optionally Substituted or a method for controlling a pest which comprises a step of N–C(Y), applying an effective amount of the compound (I) or a salt 0080 Y and Y are each independently a lower alkyl thereof to a pest or a habitat of pests. group optionally Substituted, a higher alkyl group, a lower US 2011/0319437 A1 Dec. 29, 2011 cycloalkyl group optionally substituted, a lower alkenyl I0084 alternatively, are formed a ring structure together group optionally substituted, a higher alkenyl group, a lower with the carbon which is bonded with each other). cycloalkenyl group optionally Substituted, a lower alkynyl 3 The compound according to 2, wherein group optionally substituted, a higher alkynyl group, an aro 0085 X is SX matic hydrocarbon group optionally Substituted or a hetero (wherein, X is a lower alkyl group optionally substituted, a cyclic group optionally Substituted, higher alkyl group, a lower cycloalkyl group optionally Sub I0081 Y is a hydrogen atom, a lower alkyl group option stituted, a lower alkenyl group optionally substituted, a higher ally Substituted, a higher alkyl group, a lower cycloalkyl alkenyl group, a lower cycloalkenyl group optionally Substi group optionally Substituted, a lower alkenyl group option tuted, a lower alkynyl group optionally Substituted, a higher ally substituted, a higher alkenyl group, a lower cycloalkenyl alkynyl group, an aromatic hydrocarbon group optionally group optionally Substituted, a lower alkynyl group option Substituted or a heterocyclic group optionally Substituted), ally Substituted, a higher alkynyl group, an aromatic hydro 10086 Y is OY, NY2Y or SY carbon group optionally substituted or a heterocyclic group (wherein, Y is a lower alkyl group optionally substituted, a optionally substituted), higher alkyl group, a lower cycloalkyl group optionally Sub 0082 Z is a lower alkyl group optionally substituted, a stituted, a lower alkenyl group optionally substituted, a higher higher alkyl group, a lower cycloalkyl group optionally Sub alkenyl group, a lower cycloalkenyl group optionally Substi stituted, a lower alkenyl group optionally substituted, a higher tuted, a lower alkynyl group optionally Substituted, a higher alkenyl group, a lower cycloalkenyl group optionally Substi alkynyl group, an aromatic hydrocarbon group optionally tuted, a lower alkynyl group optionally Substituted, a higher Substituted, a heterocyclic group optionally Substituted or alkynyl group, an aromatic hydrocarbon group optionally N–C(Y), Substituted, a heterocyclic group optionally Substituted, I0087 Yi and Y are each independently a lower alkyl C(=O)CZ (wherein, Z is a lower alkyl group optionally group optionally Substituted, a higher alkyl group, a lower Substituted, a higher alkyl group, a lower cycloalkyl group cycloalkyl group optionally substituted, a lower alkenyl optionally Substituted, a lower alkenyl group optionally Sub group optionally substituted, a higher alkenyl group, a lower stituted, a higher alkenyl group, a lower cycloalkenyl group cycloalkenyl group optionally Substituted, a lower alkynyl optionally Substituted, a lower alkynyl group optionally Sub group optionally substituted, a higher alkynyl group, an aro stituted, a higher alkynyl group, an aromatic hydrocarbon matic hydrocarbon group optionally Substituted or a hetero group optionally Substituted or a heterocyclic group option cyclic group optionally Substituted, ally substituted), 10088 Y is a hydrogen atom, a lower alkyl group option SO.Z (wherein, Z is a lower alkyl group optionally substi ally Substituted, a higher alkyl group, a lower cycloalkyl tuted, a higher alkyl group, a lower cycloalkyl group option group optionally Substituted, a lower alkenyl group option ally substituted, a lower alkenyl group optionally Substituted, ally Substituted, a higher alkenyl group, a lower cycloalkenyl a higher alkenyl group, a lower cycloalkenyl group optionally group optionally Substituted, a lower alkynyl group option Substituted, a lower alkynyl group optionally Substituted, a ally Substituted, a higher alkynyl group, an aromatic hydro higher alkynyl group, an aromatic hydrocarbon group option carbon group optionally substituted or a heterocyclic group ally Substituted, a heterocyclic group optionally substituted or optionally substituted), I0089 Z is a lower alkyl group optionally substituted, a an amino group optionally substituted), higher alkyl group, a lower cycloalkyl group optionally Sub NZZ (wherein, Z and Z are each independently a hydro stituted, a lower alkenyl group optionally substituted, a higher gen atom, a lower alkyl group optionally Substituted, a higher alkenyl group, a lower cycloalkenyl group optionally Substi alkyl group, a lower cycloalkyl group optionally Substituted, tuted, a lower alkynyl group optionally Substituted, a higher a lower alkenyl group optionally Substituted, a higher alkenyl alkynyl group, an aromatic hydrocarbon group optionally group, a lower cycloalkenyl group optionally substituted, a Substituted, a heterocyclic group optionally Substituted, lower alkynyl group optionally Substituted, a higher alkynyl C(=O)CZ (wherein, Z is a lower alkyl group optionally group, an aromatic hydrocarbon group optionally Substituted Substituted, a higher alkyl group, a lower cycloalkyl group or a heterocyclic group optionally Substituted, optionally Substituted, a lower alkenyl group optionally Sub 0083) alternatively, are formed a ring structure together stituted, a higher alkenyl group, a lower cycloalkenyl group with the nitrogen which is bonded with each other), optionally Substituted, a lower alkynyl group optionally Sub OZ (wherein, Z is a lower alkyl group optionally substi stituted, a higher alkynyl group, an aromatic hydrocarbon tuted, a higher alkyl group, a lower cycloalkyl group option group optionally Substituted or a heterocyclic group option ally substituted, a lower alkenyl group optionally Substituted, ally substituted), a higher alkenyl group, a lower cycloalkenyl group optionally SO.Z (wherein, Z is a lower alkyl group optionally substi Substituted, a lower alkynyl group optionally Substituted, a tuted, a higher alkyl group, a lower cycloalkyl group option higher alkynyl group, an aromatic hydrocarbon group option ally substituted, a lower alkenyl group optionally Substituted, ally Substituted or a heterocyclic group optionally Substi a higher alkenyl group, a lower cycloalkenyl group optionally tuted), or Substituted, a lower alkynyl group optionally Substituted, a N=C(Z) (wherein, Z's are each independently a hydrogen higher alkynyl group, an aromatic hydrocarbon group option atom, a lower alkyl group optionally Substituted, a higher ally Substituted, a heterocyclic group optionally substituted or alkyl group, a lower cycloalkyl group optionally Substituted, an amino group optionally substituted), a lower alkenyl group optionally Substituted, a higher alkenyl NZZ (wherein, Z and Z are each independently a hydro group, a lower cycloalkenyl group optionally substituted, a gen atom, a lower alkyl group optionally Substituted, a higher lower alkynyl group optionally Substituted, a higher alkynyl alkyl group, a lower cycloalkyl group optionally Substituted, group, an aromatic hydrocarbon group optionally Substituted a lower alkenyl group optionally Substituted, a higher alkenyl or a heterocyclic group optionally Substituted, group, a lower cycloalkenyl group optionally substituted, a US 2011/0319437 A1 Dec. 29, 2011 lower alkynyl group optionally Substituted, a higher alkynyl pendent Substituent (s) selected from the group consisting of group, an aromatic hydrocarbon group optionally Substituted (1) a halogen atom, (2) a nitro group, (3) a lower alkyl group, or a heterocyclic group optionally Substituted, (4) a lower haloalkyl group and (5) a lower alkoxy group; or 0090 alternatively, are formed a ring structure together a heterocyclic group optionally Substituted with one or more with the nitrogen which is bonded with each other), lower alkyl group(s)), OZ (wherein, Z is a lower alkyl group optionally substi 0.098 Y is OY, NYY or SY tuted, a higher alkyl group, a lower cycloalkyl group option (wherein,Y' is a lower alkyl group optionally substituted with ally substituted, a lower alkenyl group optionally Substituted, at least one substituent selected from the group consisting of a higher alkenyl group, a lower cycloalkenyl group optionally (1) an aromatic hydrocarbon group optionally Substituted Substituted, a lower alkynyl group optionally Substituted, a with at least one lower alkyl group, (2) an aromatic hydrocar higher alkynyl group, an aromatic hydrocarbon group option bon group Substituted with at least one halogen and (3) a ally Substituted or a heterocyclic group optionally Substi heterocyclic group Substituted with at least one halogen; an tuted), or aromatic hydrocarbon group optionally Substituted with one N=C(Z) (wherein, Z's are each independently a hydrogen or more independent Substituent(s) selected from the group atom, a lower alkyl group optionally Substituted, a higher consisting of (1) a halogen, (2) a cyano group, (3) a nitro alkyl group, a lower cycloalkyl group optionally Substituted, group, (4) a lower alkyl group, (5) anamino group, (6) a lower a lower alkenyl group optionally Substituted, a higher alkenyl alkylthio group, (7) a lower alkylsulfonyl group, (8) a lower group, a lower cycloalkenyl group optionally substituted, a cycloalkyl group, (9) an aromatic hydrocarbon group, (10) a lower alkynyl group optionally Substituted, a higher alkynyl lower alkoxycarbonyl group, (11) a lower alkoxy group, (12) group, an aromatic hydrocarbon group optionally Substituted a heterocyclic group, (13) a lower alkylene group and (14) a or a heterocyclic group optionally Substituted, lower alkylenedioxy group; a heterocyclic group; or a lower 0091 alternatively, are formed a ring structure together alkylidene amino group optionally Substituted at least one with the carbon which is bonded with each other). aromatic hydrocarbon group, 4 The compound according to 3, wherein I0099 Y is a lower alkyl group optionally substituted with 0092 X is SX at least one aromatic hydrocarbon group, or an aromatic (wherein, X is a lower alkyl group optionally substituted, a hydrocarbon group, higher alkyl group, a lower alkenyl group optionally Substi 0100 Y is a lower alkyl group, tuted, a lower cycloalkyl group optionally substituted, an 10101 Y is a lower alkyl group optionally substituted with aromatic hydrocarbon group optionally substituted or a het at least one substituent selected from the group consisting of erocyclic group optionally Substituted), (1) an aromatic hydrocarbon group optionally Substituted 0093 Y is OY, NY2Y or SY with at least one halogen, (2) an aromatic hydrocarbon group (wherein, Y is a lower alkyl group optionally substituted, an optionally substituted with at least one lower alkyl group and aromatic hydrocarbon group optionally substituted, a hetero (3) a lower cycloalkyl group; a lower cycloalkyl group; an cyclic group optionally substituted or N=C(Y) (Y's are aromatic hydrocarbon group optionally Substituted with one each independently a lower alkyl group or an aromatic hydro or more independent Substituent(s) selected from the group carbon group), consisting of (1) a halogen, (2) a lower alkyl group optionally 0094. Y° and Y are each independently a lower alkyl Substituted with at least one halogen, (3) a lower alkoxy group group optionally Substituted or an aromatic hydrocarbon and (4) a lower haloalkyloxy group; a heterocyclic group group optionally Substituted, optionally substituted with one or more independent substitu I0095 Y is a lower alkyl group optionally substituted, a ent (s) selected from the group consisting of (1) a lower alkyl lower cycloalkyl group optionally Substituted, a lower alk group, (2) a lower haloalkyl group and (3) a heterocyclic enyl group optionally Substituted, a lower alkynyl group group Substituted with at least one halogen; a lower alkenyl optionally substituted or a heterocyclic group optionally Sub group optionally Substituted with at least one halogen; or a stituted), lower alkynyl group), 0096 Z is a lower alkyl group optionally substituted, an 0102 Z is a lower alkyl group substituted with at least one aromatic hydrocarbon group optionally substituted, a hetero halogen; an aromatic hydrocarbon group optionally Substi cyclic group optionally substituted, a lower alkoxycarbonyl tuted with one or more independent substituent(s) selected group, an aromatic hydrocarbon Sulfonyl group optionally from the group consisting of (1) a halogen, (2) a nitro group, Substituted, an amino group Substituted with an aromatic (3) a cyano group, (4) a lower alkyl group, (5) a lower alkoxy hydrocarbon group and optionally Substituted with a lower group, (6) a lower haloalkyl group, (7) a lower cycloalkyl alkyl group, an aromatic hydrocarbon oxy group, a lower group and (8) an aromatic hydrocarbon oxy group; a hetero alkoxy group Substituted with at least one aromatic hydrocar cyclic group; a lower alkoxycarbonyl group; an aromatic bon group or a lower alkylidene amino group Substituted with hydrocarbon Sulfonyl group; an amino group Substituted with at least one aromatic hydrocarbon group. an aromatic hydrocarbon group and optionally Substituted 5 The compound according to 4, wherein with a lower alkyl group; an aromatic hydrocarbon oxy 0097 X is SX group; a lower alkoxy group Substituted with at least one (wherein, X is a lower alkyl group optionally substituted aromatic hydrocarbon group, or a lower alkylidene amino with at least one Substituent selected from the group consist group Substituted with at least one aromatic hydrocarbon ing of (1) an aromatic hydrocarbon group optionally Substi group. tuted with at least one halogen, lower alkyl group or lower 6. The compound according to 2, wherein alkoxy group and (2) a heterocyclic group optionally Substi (0103 X is OX' tuted with at least one halogen; a higher alkyl group; a lower (wherein, X is a lower alkyl group optionally substituted, a alkenyl group; a lower cycloalkyl group; an aromatic hydro higher alkyl group, a lower cycloalkyl group optionally Sub carbon group optionally Substituted with one or more inde stituted, a lower alkenyl group optionally substituted, a higher US 2011/0319437 A1 Dec. 29, 2011 alkenyl group, a lower cycloalkenyl group optionally Substi OZ (wherein, Z is a lower alkyl group optionally substi tuted, a lower alkynyl group optionally Substituted, a higher tuted, a higher alkyl group, a lower cycloalkyl group option alkynyl group, an aromatic hydrocarbon group optionally ally substituted, a lower alkenyl group optionally Substituted, Substituted, a heterocyclic group optionally Substituted, a higher alkenyl group, a lower cycloalkenyl group optionally NXGXH, O N=C(X)), Substituted, a lower alkynyl group optionally Substituted, a 01.04 Y is OY, NYY or SY higher alkynyl group, an aromatic hydrocarbon group option (wherein, Y is a lower alkyl group optionally substituted, a ally Substituted or a heterocyclic group optionally Substi higher alkyl group, a lower cycloalkyl group optionally Sub tuted), or stituted, a lower alkenyl group optionally substituted, a higher N=C(Z) (wherein, Z's are each independently a hydrogen alkenyl group, a lower cycloalkenyl group optionally Substi atom, a lower alkyl group optionally Substituted, a higher tuted, a lower alkynyl group optionally Substituted, a higher alkyl group, a lower cycloalkyl group optionally Substituted, alkynyl group, an aromatic hydrocarbon group optionally a lower alkenyl group optionally Substituted, a higher alkenyl Substituted, a heterocyclic group optionally Substituted, or group, a lower cycloalkenyl group optionally substituted, a N–C(Y), lower alkynyl group optionally Substituted, a higher alkynyl 0105 Y and Y are each independently a lower alkyl group, an aromatic hydrocarbon group optionally Substituted group optionally substituted, a higher alkyl group, a lower or a heterocyclic group optionally Substituted, cycloalkyl group optionally substituted, a lower alkenyl 0109 alternatively, are formed a ring structure together group optionally substituted, a higher alkenyl group, a lower with the carbon which is bonded with each other). cycloalkenyl group optionally Substituted, a lower alkynyl 7. The compound according to 6, wherein group optionally substituted, a higher alkynyl group, an aro 0110 X is OX' matic hydrocarbon group optionally Substituted, or a hetero (wherein, X" is a lower alkyl group optionally substituted, an cyclic group optionally Substituted, aromatic hydrocarbon group optionally substituted, a lower 0106 Y is a hydrogen atom, a lower alkyl group option cycloalkyl group optionally Substituted, a di-lower alkyl ally Substituted, a higher alkyl group, a lower cycloalkyl amino group, a lower alkylidene amino group optionally Sub group optionally Substituted, a lower alkenyl group option stituted, or a lower cycloalkylidene amino group optionally ally substituted, a higher alkenyl group, a lower cycloalkenyl substituted), group optionally Substituted, a lower alkynyl group option 0111 Y is OY" or SY ally Substituted, a higher alkynyl group, an aromatic hydro (wherein, Y and Y are each independently a lower alkyl carbon group optionally substituted, or a heterocyclic group group optionally substituted, or an aromatic hydrocarbon optionally substituted), group optionally Substituted), 0107 Z is a lower alkyl group optionally substituted, a 0112 Z is an aromatic hydrocarbon group optionally Sub higher alkyl group, a lower cycloalkyl group optionally Sub stituted or a heterocyclic group optionally substituted. stituted, a lower alkenyl group optionally substituted, a higher 8. The compound according to 7, wherein alkenyl group, a lower cycloalkenyl group optionally Substi 0113 X is OX' tuted, a lower alkynyl group optionally Substituted, a higher (wherein, X" is a lower alkyl group substituted with at least alkynyl group, an aromatic hydrocarbon group optionally one aromatic hydrocarbon group optionally substituted with one or more independent substituent(s) selected from the Substituted, a heterocyclic group optionally Substituted, group consisting of (1) a halogen, (2) a lower alkyl group and C(=O)CZ' (wherein, Z' is a lower alkyl group optionally (3) a lower alkoxy group; lower cycloalkyl group; an aromatic Substituted, a higher alkyl group, a lower cycloalkyl group hydrocarbon group optionally Substituted with one or more optionally Substituted, a lower alkenyl group optionally Sub independent Substituent(s) selected from the group consisting stituted, a higher alkenyl group, a lower cycloalkenyl group of (1) a halogen, (2) a lower alkyl group optionally Substituted optionally Substituted, a lower alkynyl group optionally Sub with at least one halogen, (3) a lower alkoxy group, (4) a stituted, a higher alkynyl group, an aromatic hydrocarbon lower alkoxycarbonyl group, (5) a lower alkanoyl group, (6) group optionally Substituted or a heterocyclic group option a lower alkylthio group, (7) an aromatic hydrocarbon group, ally substituted), (8) a cyano group, (9) a nitro group and (10) an alkylenedioxy SOZ (wherein, Z is a lower alkyl group optionally substi group; an alkylidene amino group optionally substituted with tuted, a higher alkyl group, a lower cycloalkyl group option at least one aromatic hydrocarbon group; a lower cycloalky ally substituted, a lower alkenyl group optionally Substituted, lidene amino group; or a di-lower alkyl amino group), a higher alkenyl group, a lower cycloalkenyl group optionally 0114 Y is OY or SY Substituted, a lower alkynyl group optionally Substituted, a (wherein, Y is a lower alkyl group substituted with at least higher alkynyl group, an aromatic hydrocarbon group option one aromatic hydrocarbon group, oranaromatic hydrocarbon ally Substituted, a heterocyclic group optionally substituted or group optionally Substituted with one or more independent an amino group optionally substituted), Substituent(s) selected from the group consisting of a halogen NZZ (wherein, Z and Z are each independently a hydro and a lower alkyl group, gen atom, a lower alkyl group optionally Substituted, a higher I0115 Y is a lower alkyl group optionally substituted with alkyl group, a lower cycloalkyl group optionally Substituted, at least one aromatic hydrocarbon group, or an aromatic a lower alkenyl group optionally Substituted, a higher alkenyl hydrocarbon group), group, a lower cycloalkenyl group optionally substituted, a 0116 Z is an aromatic hydrocarbon group optionally sub lower alkynyl group optionally Substituted, a higher alkynyl stituted with one or more independent substituent(s) selected group, an aromatic hydrocarbon group optionally Substituted from the group consisting of (1) a halogen, (2) a lower or a heterocyclic group optionally Substituted, cycloalkylthio group, (3) a hydroxyl group, (4) a lower alkyl 0108 alternatively, are formed a ring structure together group optionally Substituted with at least one aromatic hydro with the nitrogen which is bonded with each other), carbon group, (5) a lower alkenyl group, (6) a lower alkoxy US 2011/0319437 A1 Dec. 29, 2011 group optionally Substituted with at least one halogen, (7) a optionally Substituted, a lower alkenyl group optionally Sub lower alkanoyloxy group, (8) an aromatic hydrocarbon group stituted, a higher alkenyl group, a lower cycloalkenyl group optionally substituted with at least one lower alkyl group or optionally Substituted, a lower alkynyl group optionally Sub halogen, (9) a heterocyclic group, (10) a lower alkylthio stituted, a higher alkynyl group, an aromatic hydrocarbon group, (11) a lower alkyl Sulfinyl group, (12) a lower alkyl group optionally Substituted or a heterocyclic group option Sulfonyl group, (13) an arylthio group, (14) a lower alkoxy ally substituted), carbonyl group, (15) a lower alkanoyl group, (16) anaromatic SO.Z (wherein, Z is a lower alkyl group optionally substi hydrocarbon carbonyl group, (17) a lower alkynyl group, (18) tuted, a higher alkyl group, a lower cycloalkyl group option a lower alkylenedioxy group and (19) a lower alkylene group; ally substituted, a lower alkenyl group optionally Substituted, or a heterocyclic group. a higher alkenyl group, a lower cycloalkenyl group optionally 9The compound according to 2, wherein Substituted, a lower alkynyl group optionally Substituted, a 0117 X is NXX, or S(O).X higher alkynyl group, an aromatic hydrocarbon group option (wherein, X and X are each independently a lower alkyl ally Substituted, a heterocyclic group optionally substituted or group optionally substituted, a higher alkyl group, a lower an amino group optionally substituted), cycloalkyl group optionally substituted, a lower alkenyl NZZ (wherein, Z and Z are each independently a hydro group optionally substituted, a higher alkenyl group, a lower gen atom, a lower alkyl group optionally Substituted, a higher cycloalkenyl group optionally Substituted, a lower alkynyl alkyl group, a lower cycloalkyl group optionally Substituted, group optionally substituted, a higher alkynyl group, an aro a lower alkenyl group optionally Substituted, a higher alkenyl matic hydrocarbon group optionally Substituted, a heterocy group, a lower cycloalkenyl group optionally substituted, a clic group optionally substituted, or C(=Q')X' (wherein, lower alkynyl group optionally Substituted, a higher alkynyl Q’ is an oxygenatom, and X" is a lower alkyl group option group, an aromatic hydrocarbon group optionally Substituted ally substituted), or a heterocyclic group optionally Substituted, I01181 X is a hydrogen atom, a lower alkyl group option I0123 alternatively, are formed a ring structure together ally Substituted, a higher alkyl group, a lower cycloalkyl with the nitrogen which is bonded with each other), group optionally Substituted, a lower alkenyl group option OZ (wherein, Z is a lower alkyl group optionally substi ally substituted, a higher alkenyl group, a lower cycloalkenyl tuted, a higher alkyl group, a lower cycloalkyl group option group optionally Substituted, a lower alkynyl group option ally substituted, a lower alkenyl group optionally Substituted, ally Substituted, a higher alkynyl group, an aromatic hydro a higher alkenyl group, a lower cycloalkenyl group optionally carbon group optionally substituted, or a heterocyclic group Substituted, a lower alkynyl group optionally Substituted, a optionally substituted), higher alkynyl group, an aromatic hydrocarbon group option 0119 Y is OY, NY2Y or SY ally Substituted or a heterocyclic group optionally Substi (wherein, Y is a lower alkyl group optionally substituted, a tuted), or higher alkyl group, a lower cycloalkyl group optionally Sub N=C(Z) (wherein, Z's are each independently a hydrogen stituted, a lower alkenyl group optionally substituted, a higher atom, a lower alkyl group optionally Substituted, a higher alkenyl group, a lower cycloalkenyl group optionally Substi alkyl group, a lower cycloalkyl group optionally Substituted, tuted, a lower alkynyl group optionally Substituted, a higher a lower alkenyl group optionally Substituted, a higher alkenyl alkynyl group, an aromatic hydrocarbon group optionally group, a lower cycloalkenyl group optionally substituted, a Substituted, a heterocyclic group optionally substituted or lower alkynyl group optionally Substituted, a higher alkynyl N–C(Y), group, an aromatic hydrocarbon group optionally Substituted 0120 Y° and Y are each independently a lower alkyl or a heterocyclic group optionally Substituted, group optionally substituted, a higher alkyl group, a lower 0.124 alternatively, are formed a ring structure together cycloalkyl group optionally substituted, a lower alkenyl with the carbon which is bonded with each other). group optionally substituted, a higher alkenyl group, a lower 10. The compound according to 9), wherein cycloalkenyl group optionally Substituted, a lower alkynyl (0.125 X is NXX, or S(O).X group optionally substituted, a higher alkynyl group, an aro (wherein, X is a lower alkyl group optionally substituted, an matic hydrocarbon group optionally Substituted or a hetero aromatic hydrocarbon group optionally Substituted, or cyclic group optionally Substituted, C(=Q')X' (wherein, Q is an oxygenatom, and X' is a 0121 Y is a hydrogen atom, a lower alkyl group option lower alkyl group optionally Substituted), ally Substituted, a higher alkyl group, a lower cycloalkyl I0126 X is a lower alkyl group optionally substituted, or group optionally Substituted, a lower alkenyl group option an aromatic hydrocarbon group optionally Substituted, ally substituted, a higher alkenyl group, a lower cycloalkenyl I0127 alternatively, X and X are formed a ring structure group optionally Substituted, a lower alkynyl group option together with the nitrogen which is bonded with each other, ally Substituted, a higher alkynyl group, an aromatic hydro I0128 X is an aromatic hydrocarbon group optionally carbon group optionally substituted or a heterocyclic group substituted), optionally substituted), 0129. Y is OY, or SY 0122 Z is a lower alkyl group optionally substituted, a (wherein, Y and Y are an aromatic hydrocarbon group higher alkyl group, a lower cycloalkyl group optionally Sub optionally substituted), stituted, a lower alkenyl group optionally substituted, a higher 0.130 Z is an aromatic hydrocarbon group optionally sub alkenyl group, a lower cycloalkenyl group optionally Substi stituted. tuted, a lower alkynyl group optionally substituted, an aro 11 The compound according to 10, wherein matic hydrocarbon group optionally Substituted, a heterocy 0131 X is NXX, or S(O).X clic group optionally substituted, (wherein, X is a lower alkyl group substituted with at least C(=O)CZ' (wherein, Z' is a lower alkyl group optionally one aromatic hydrocarbon group, an aromatic hydrocarbon Substituted, a higher alkyl group, a lower cycloalkyl group group or a lower alkanoyl group, US 2011/0319437 A1 Dec. 29, 2011

(0132) X is a lower alkyl group or an aromatic hydrocar stituted, a higher alkynyl group, an aromatic hydrocarbon bon group, group optionally Substituted or a heterocyclic group option I0133) alternatively, X and X are formed a piperidino ally substituted), group or morpholino group together with the nitrogen which SOZ (wherein, Z is a lower alkyl group optionally substi is bonded with each other, tuted, a higher alkyl group, a lower cycloalkyl group option I0134) X is an aromatic hydrocarbon group), ally substituted, a lower alkenyl group optionally Substituted, a higher alkenyl group, a lower cycloalkenyl group optionally 0135 Y is OY", or SY Substituted, a lower alkynyl group optionally Substituted, a (wherein, Y and SY are an aromatic hydrocarbon group), higher alkynyl group, an aromatic hydrocarbon group option 0.136 Z is an aromatic hydrocarbon group. ally Substituted, a heterocyclic group optionally substituted or 12 The compound according to 2, wherein an amino group optionally substituted), 10137 X is OX', NXX, SX or S(O).X NZZ (wherein, Z and Z are each independently a hydro (wherein, X and X’ are a lower alkyl group optionally sub gen atom, a lower alkyl group optionally Substituted, a higher stituted, a higher alkyl group, a lower cycloalkyl group alkyl group, a lower cycloalkyl group optionally Substituted, optionally Substituted, a lower alkenyl group optionally Sub a lower alkenyl group optionally Substituted, a higher alkenyl stituted, a higher alkenyl group, a lower cycloalkenyl group group, a lower cycloalkenyl group optionally substituted, a optionally Substituted, a lower alkynyl group optionally Sub lower alkynyl group optionally Substituted, a higher alkynyl stituted, a higher alkynyl group, an aromatic hydrocarbon group, an aromatic hydrocarbon group optionally Substituted group optionally Substituted, a heterocyclic group optionally or a heterocyclic group optionally Substituted, substituted, C(=Q')X' (wherein, Q is an oxygen atom, 0.143 alternatively, are formed a ring structure together and X" is a lower alkyl group optionally substituted), with the nitrogen which is bonded with each other), NXGXHI, O N=C(X), OZ (wherein, Z is a lower alkyl group optionally substi I0138 X and X are each independently a lower alkyl tuted, a higher alkyl group, a lower cycloalkyl group option group optionally substituted, a higher alkyl group, a lower ally substituted, a lower alkenyl group optionally Substituted, cycloalkyl group optionally substituted, a lower alkenyl a higher alkenyl group, a lower cycloalkenyl group optionally group optionally substituted, a higher alkenyl group, a lower Substituted, a lower alkynyl group optionally Substituted, a cycloalkenyl group optionally Substituted, a lower alkynyl higher alkynyl group, an aromatic hydrocarbon group option group optionally substituted, a higher alkynyl group, an aro ally Substituted or a heterocyclic group optionally Substi matic hydrocarbon group optionally Substituted, a heterocy tuted), or clic group optionally substituted, or C(=Q)X' (wherein, N=C(Z) (wherein, Z's are each independently a hydrogen Q'' is an oxygenatom, and X" is a lower alkyl group option atom, a lower alkyl group optionally Substituted, a higher ally substituted), alkyl group, a lower cycloalkyl group optionally Substituted, I0139 X is a hydrogen atom, a lower alkyl group option a lower alkenyl group optionally Substituted, a higher alkenyl ally Substituted, a higher alkyl group, a lower cycloalkyl group, a lower cycloalkenyl group optionally substituted, a group optionally Substituted, a lower alkenyl group option lower alkynyl group optionally Substituted, a higher alkynyl ally substituted, a higher alkenyl group, a lower cycloalkenyl group, an aromatic hydrocarbon group optionally Substituted group optionally Substituted, a lower alkynyl group option or a heterocyclic group optionally Substituted, ally Substituted, a higher alkynyl group, an aromatic hydro 0144) alternatively, are formed a ring structure together carbon group optionally Substituted, or a heterocyclic group with the carbon which is bonded with each other). optionally substituted, 13 The compound according to 12, wherein I0140) alternatively, X and X are formed a ring structure (0145 X is OX', NXX, SX or S(O).X. together with the nitrogen which is bonded with each other, (wherein, X" is a lower alkyl group optionally substituted, an 0141 Y is OY aromatic hydrocarbon group optionally substituted, a lower (wherein, Y is a lower alkyl group optionally substituted, a cycloalkyl group optionally Substituted, a di-lower alkyl higher alkyl group, a lower cycloalkyl group optionally Sub amino group, a lower alkylidene amino group optionally Sub stituted, a lower alkenyl group optionally substituted, a higher stituted, a lower cycloalkylidene amino group optionally Sub alkenyl group, a lower cycloalkenyl group optionally Substi stituted, tuted, a lower alkynyl group optionally Substituted, a higher I014.6 X is a lower alkyl group optionally substituted, an alkynyl group, an aromatic hydrocarbon group optionally aromatic hydrocarbon group optionally Substituted, or Substituted, a heterocyclic group optionally substituted or C(=Q')X' (wherein, Q is an oxygenatom, and X' is a N–C(Y), lower alkyl group optionally Substituted), 0142 Z is a cyano group, a lower alkyl group optionally 10147 X is allower alkyl group optionally substituted oran Substituted, a higher alkyl group, a lower cycloalkyl group aromatic hydrocarbon group optionally Substituted, optionally Substituted, a lower alkenyl group optionally Sub 10148 alternatively, X and X are formed a ring structure stituted, a higher alkenyl group, a lower cycloalkenyl group together with the nitrogen which is bonded with each other, optionally Substituted, a lower alkynyl group optionally Sub 10149 X is a lower alkyl group optionally substituted, a stituted, a higher alkynyl group, an aromatic hydrocarbon higher alkyl group, a lower alkenyl group optionally Substi group optionally Substituted, a heterocyclic group optionally tuted, a lower cycloalkyl group optionally substituted, an substituted, aromatic hydrocarbon group optionally substituted, or a het C(=O)CZ' (wherein, Z' is a lower alkyl group optionally erocyclic group optionally substituted, X is an aromatic Substituted, a higher alkyl group, a lower cycloalkyl group hydrocarbon group optionally Substituted), optionally Substituted, a lower alkenyl group optionally Sub O150 Y is OY stituted, a higher alkenyl group, a lower cycloalkenyl group (wherein, Y is a lower alkyl group optionally substituted, an optionally Substituted, a lower alkynyl group optionally Sub aromatic hydrocarbon group optionally substituted, a hetero US 2011/0319437 A1 Dec. 29, 2011 cyclic group optionally substituted or N=C(Y) (Y's are from the group consisting of (1) a halogen, (2) a cyano group, each independently a lower alkyl group or an aromatic hydro (3) a hydroxy group, (4) a lower alkyl group optionally Sub carbon group) stituted with at least one halogen or aromatic hydrocarbon 0151 Z is an aromatic hydrocarbon group optionally sub group, (5) a lower alkenyl group, (6) a lower alkoxy group stituted, or a heterocyclic group optionally Substituted. optionally substituted with at least one halogen, (7) a lower 14 The compound according to 13, wherein alkanoyl oxy group, (8) an aromatic hydrocarbon group 0152 X is OX', NXX, SX or S(O).X optionally substituted with at least one halogen or lower alkyl (wherein, X" is a lower alkyl group substituted with at least group, (9) a heterocyclic group, (10) a lower alkylthio group, one aromatic hydrocarbon group optionally substituted with (11) a lower alkyl sulfinyl group, (12) a lower alkyl sulfonyl one or more independent substituent(s) selected from the group, (13) an arylthio group, (14) a lower alkoxy carbonyl group consisting of (1) a halogen, (2) a lower alkyl group and group, (15) a lower alkanoyl group, (16) an aromatic hydro (3) a lower alkoxy group; an aromatic hydrocarbon group carbon carbonyl group, (17) a lower alkynyl group, (18) a optionally substituted with one or more independent substitu lower cycloalkylthio group, (19) a lower alkylene dioxy ent(s) selected from the group consisting of (1) a halogen, (2) group, (20) a lower alkylene group, (21) a lower cycloalkyl a lower alkyl group optionally substituted with at least one group, (22) an aryloxy group and (23) a nitro group; a het halogen, (3) a lower alkoxy group, (4) a lower alkoxycarbonyl erocyclic group. group, (5) a lower alkanoyl group, (6) a lower alkylthio group, 15 The compound according to 2, wherein (7) an aromatic hydrocarbon group, (8) a cyano group, (9) a 10159 X is OX', NXX, SX or S(O).X. nitro group and (10) an alkylenedioxy group; a lower (wherein, X and X’ are a lower alkyl group optionally sub cycloalkyl group; an alkylidene amino group optionally Sub stituted, a higher alkyl group, a lower cycloalkyl group stituted with at least one aromatic hydrocarbon group; a lower optionally Substituted, a lower alkenyl group optionally Sub cycloalkylidene amino group; or a di-lower alkyl amino stituted, a higher alkenyl group, a lower cycloalkenyl group grOup, optionally Substituted, a lower alkynyl group optionally Sub 0153 X is a lower alkyl group substituted with at least stituted, a higher alkynyl group, an aromatic hydrocarbon one aromatic hydrocarbon group, an aromatic hydrocarbon group optionally Substituted, a heterocyclic group optionally group, or a lower alkanoyl group, substituted, C(=Q')X' (wherein, Q’ is an oxygen atom, I0154) X is a lower alkyl group or an aromatic hydrocar and X' is a lower alkyl group optionally substituted), bon group, NXX or N. C(X), O155 alternatively, X and X are formed a piperidino (0160 X and X are each independently a lower alkyl group or a morpholino group together with the nitrogen group optionally Substituted, a higher alkyl group, a lower which is bonded with each other, cycloalkyl group optionally substituted, a lower alkenyl I0156 X is a lower alkyl group optionally substituted with group optionally substituted, a higher alkenyl group, a lower at least one substituent selected from the group consisting of cycloalkenyl group optionally Substituted, a lower alkynyl (1) an aromatic hydrocarbon group optionally Substituted group optionally substituted, a higher alkynyl group, an aro with at least one halogen, lower alkyl group or lower alkoxy matic hydrocarbon group optionally Substituted, a heterocy group and (2) a heterocyclic group optionally Substituted with clic group optionally substituted or C(=Q')X' (wherein, at least one halogen; a higher alkyl group; a lower alkenyl Q’ is an oxygenatom, and X" is a lower alkyl group option group; a lower cycloalkyl group; an aromatic hydrocarbon ally substituted), group optionally Substituted with one or more independent (0161 X is a hydrogen atom, a lower alkyl group option Substituent (s) selected from the group consisting of (1) a ally Substituted, a higher alkyl group, a lower cycloalkyl halogenatom, (2) a nitro group, (3) a lower alkyl group, (4) a group optionally Substituted, a lower alkenyl group option lower haloalkyl group and (5) a lower alkoxy group; or a ally Substituted, a higher alkenyl group, a lower cycloalkenyl heterocyclic group optionally substituted with one or more group optionally Substituted, a lower alkynyl group option lower alkyl group(s), X is an aromatic hydrocarbon group), ally Substituted, a higher alkynyl group, an aromatic hydro 0157, Y is OY, carbon group optionally substituted or a heterocyclic group (wherein,Y' is a lower alkyl group optionally substituted with optionally substituted, one or more Substituent(s) selected from the group consisting of (1) an aromatic hydrocarbon group optionally Substituted (0162 alternatively, X and X are formed a ring structure with at least one lower alkyl group, (2) an aromatic hydrocar together with the nitrogen which is bonded with each other), bon group Substituted with at least one halogen and (3) a 0163 Y is SY heterocyclic group Substituted with at least one halogen; an (wherein, Y is a lower alkyl group optionally substituted, a aromatic hydrocarbon group optionally Substituted with one higher alkyl group, a lower cycloalkyl group optionally Sub or more independent Substituent(s) selected from the group stituted, a lower alkenyl group optionally substituted, a higher consisting of (1) a halogen, (2) a cyano group, (3) a nitro alkenyl group, a lower cycloalkenyl group optionally Substi group, (4) a lower alkyl group, (5) anamino group, (6) a lower tuted, a lower alkynyl group optionally Substituted, a higher alkylthio group, (7) a lower alkyl Sulfonyl group, (8) a lower alkynyl group, an aromatic hydrocarbon group optionally cycloalkyl group, (9) an aromatic hydrocarbon group, (10) a Substituted or a heterocyclic group optionally Substituted), lower alkoxycarbonyl group, (11) a lower alkoxy group, (12) 0164 Z is a lower alkyl group optionally substituted, a a heterocyclic group, (13) a lower alkylenedioxy group and higher alkyl group, a lower cycloalkyl group optionally Sub (14) a lower alkylene group; a heterocyclic group; or a lower stituted, a lower alkenyl group optionally substituted, a higher alkylidene amino group optionally Substituted at least one alkenyl group, a lower cycloalkenyl group optionally Substi aromatic hydrocarbon group), tuted, a lower alkynyl group optionally Substituted, a higher 0158 Z is an aromatic hydrocarbon group optionally sub alkynyl group, an aromatic hydrocarbon group optionally stituted with one or more independent substituent(s) selected Substituted, a heterocyclic group optionally Substituted, US 2011/0319437 A1 Dec. 29, 2011

C(=O)CZ (wherein, Z is a lower alkyl group optionally with a lower alkyl group, anaromatic hydrocarbon oxy group, Substituted, a higher alkyl group, a lower cycloalkyl group a lower alkoxy group Substituted with at least one aromatic optionally Substituted, a lower alkenyl group optionally Sub hydrocarbon group, or a lower alkylidene amino group stituted, a higher alkenyl group, a lower cycloalkenyl group optionally substituted with at least one aromatic hydrocarbon optionally Substituted, a lower alkynyl group optionally Sub group. stituted, a higher alkynyl group, an aromatic hydrocarbon 17. The compound according to 16, wherein group optionally Substituted or a heterocyclic group option (0170 X is OX', SX or S(O).X ally substituted), (wherein, X' represents an aromatic hydrocarbon group, X is SOZ (wherein, Z is a lower alkyl group optionally substi a lower alkyl group optionally Substituted with at least one tuted, a higher alkyl group, a lower cycloalkyl group option aromatic hydrocarbon group optionally Substituted with one ally substituted, a lower alkenyl group optionally Substituted, or more independent Substituent(s) selected from the group a higher alkenyl group, a lower cycloalkenyl group optionally consisting of (1) a halogen, (2) a lower alkyl group and (3) a Substituted, a lower alkynyl group optionally Substituted, a lower alkoxy group; a lower cycloalkyl group; an aromatic higher alkynyl group, an aromatic hydrocarbon group option hydrocarbon group optionally Substituted with one or more ally Substituted, a heterocyclic group optionally substituted or independent Substituent(s) selected from the group consisting an amino group optionally substituted), of (1) a halogen, (2) a lower alkyl group optionally Substituted NZZ (wherein, Z and Z are each independently a hydro with at least one halogen, (3) a lower alkoxy group, (4) a nitro gen atom, a lower alkyl group optionally Substituted, a higher group; or a heterocyclic group, alkyl group, a lower cycloalkyl group optionally Substituted, (0171 X is an aromatic hydrocarbon group), a lower alkenyl group optionally Substituted, a higher alkenyl 0172 Y is SY group, a lower cycloalkenyl group optionally substituted, a (wherein,Y is a lower alkyl group optionally substituted with lower alkynyl group optionally Substituted, a higher alkynyl at least one substituent selected from the group consisting of group, an aromatic hydrocarbon group optionally Substituted (1) an aromatic hydrocarbon group optionally Substituted or a heterocyclic group optionally Substituted, with at least one halogen, (2) an aromatic hydrocarbon group 0.165 alternatively, are formed a ring structure together optionally substituted with at least one lower alkyl group and with the nitrogen which is bonded with each other), (3) a lower cycloalkyl group; a higher alkyl group; a lower OZ (wherein, Z is a lower alkyl group optionally substi cycloalkyl group; an aromatic hydrocarbon group optionally tuted, a higher alkyl group, a lower cycloalkyl group option substituted with one or more independent substituent(s) ally substituted, a lower alkenyl group optionally substituted, Selected from the group consisting of (1) a halogen, (2) a a higher alkenyl group, a lower cycloalkenyl group optionally lower alkyl group optionally Substituted with at least one Substituted, a lower alkynyl group optionally Substituted, a halogen, (3) a lower alkoxy group and (4) a lower haloalky higher alkynyl group, an aromatic hydrocarbon group option loxy group; a heterocyclic group optionally Substituted with ally Substituted or a heterocyclic group optionally Substi one or more independent substituent(s) selected from the tuted), or group consisting of (1) a lower alkyl group, (2) a lower N=C(Z) (wherein, Z's are each independently a hydrogen haloalkyl group and (3) a heterocyclic group Substituted with atom, a lower alkyl group optionally Substituted, a higher at least one halogen; a lower alkenyl group optionally Substi alkyl group, a lower cycloalkyl group optionally Substituted, tuted with at least one halogen; a higher alkenyl group; or a a lower alkenyl group optionally Substituted, a higher alkenyl lower alkynyl group), group, a lower cycloalkenyl group optionally substituted, a 0173 Z is a lower alkyl group substituted with at least one lower alkynyl group optionally Substituted, a higher alkynyl halogen; an aromatic hydrocarbon group optionally Substi group, an aromatic hydrocarbon group optionally Substituted tuted with one or more independent substituent(s) selected or a heterocyclic group optionally Substituted, from the group consisting of (1) a halogen, (2) a lower alkyl 0166 alternatively, are formed a ring structure together group and (3) a lower alkoxy group; a lower alkoxycarbonyl with the carbon which is bonded with each other). group; an aromatic hydrocarbon Sulfonyl group optionally 16. The compound according to 15, wherein Substituted; an amino group Substituted with an aromatic (0167 X is OX', SX or S(O).X hydrocarbon group and optionally Substituted with a lower (wherein, X is an aromatic hydrocarbon group optionally alkyl group; an aromatic hydrocarbon oxy group; a lower substituted, X is a lower alkyl group optionally substituted, a alkoxy group Substituted with at least one aromatic hydrocar lower cycloalkyl group optionally Substituted, an aromatic bon group; or a lower alkylidene amino group Substituted hydrocarbon group optionally substituted or a heterocyclic with at least one aromatic hydrocarbon group. group optionally substituted, and X is an aromatic hydrocar 18. The compound according to 15, wherein bon group optionally substituted), (0174 X is OX', NXX, SX or S(O).X. 0168 Y is SY (wherein, X and X’ are a lower alkyl group optionally sub (wherein, Y is a lower alkyl group optionally substituted, a stituted, a higher alkyl group, a lower cycloalkyl group higher alkyl group, a lower cycloalkyl group optionally Sub optionally Substituted, a lower alkenyl group optionally Sub stituted, a lower alkenyl group optionally substituted, a higher stituted, a higher alkenyl group, a lower cycloalkenyl group alkenyl group, a lower alkynyl group optionally Substituted, optionally Substituted, a lower alkynyl group optionally Sub an aromatic hydrocarbon group optionally substituted or a stituted, a higher alkynyl group, an aromatic hydrocarbon heterocyclic group optionally Substituted), group optionally Substituted, a heterocyclic group optionally 0169 Z is a lower alkyl group optionally substituted, an substituted, C(=Q')X' (wherein, Q is an oxygen atom, aromatic hydrocarbon group optionally Substituted, a lower and X" is a lower alkyl group optionally substituted), alkoxycarbonyl group, an aromatic hydrocarbon Sulfonyl NXX or N CCX), group optionally substituted, an amino group Substituted with (0175 X and X are each independently a lower alkyl an aromatic hydrocarbon group and optionally Substituted group optionally Substituted, a higher alkyl group, a lower US 2011/0319437 A1 Dec. 29, 2011 cycloalkyl group optionally substituted, a lower alkenyl alkyl group, a lower cycloalkyl group optionally Substituted, group optionally substituted, a higher alkenyl group, a lower a lower alkenyl group optionally Substituted, a higher alkenyl cycloalkenyl group optionally Substituted, a lower alkynyl group, a lower cycloalkenyl group optionally substituted, a group optionally substituted, a higher alkynyl group, an aro lower alkynyl group optionally Substituted, a higher alkynyl matic hydrocarbon group optionally Substituted, a heterocy group, an aromatic hydrocarbon group optionally Substituted clic group optionally substituted or C(=Q')X' (wherein, or a heterocyclic group optionally Substituted, Q'' is an oxygenatom, and X" is a lower alkyl group option 0181 alternatively, are formed a ring structure together ally substituted), (0176 X is a hydrogen atom, a lower alkyl group option with the carbon which is bonded with each other). ally Substituted, a higher alkyl group, a lower cycloalkyl 19. The compound according to 18, wherein group optionally Substituted, a lower alkenyl group option 0182 X is OX', SX or S(O).X ally substituted, a higher alkenyl group, a lower cycloalkenyl (wherein, X' represents an aromatic hydrocarbon group group optionally Substituted, a lower alkynyl group option optionally substituted, ally Substituted, a higher alkynyl group, an aromatic hydro 0183 X is a lower alkyl group optionally substituted, a carbon group optionally substituted or a heterocyclic group lower cycloalkyl group optionally Substituted, or an aromatic optionally substituted, hydrocarbon group optionally Substituted, (0177 alternatively, X and X are formed a ring structure 0184 X is an aromatic hydrocarbon group optionally together with the nitrogen which is bonded with each other), substituted), 0178 Y is SY (wherein, Y is an aromatic hydrocarbon group optionally 0185. Y is SY Substituted or a heterocyclic group optionally Substituted), (wherein, Y is an aromatic hydrocarbon group optionally 0179 Z is a lower alkyl group optionally substituted, a Substituted or a heterocyclic group optionally Substituted), higher alkyl group, a lower cycloalkyl group optionally Sub 0186 Z is a lower alkyl group optionally substituted, an stituted, a lower alkenyl group optionally substituted, a higher aromatic hydrocarbon group optionally substituted, a lower alkenyl group, a lower cycloalkenyl group optionally Substi alkoxycarbonyl group, an aromatic hydrocarbon Sulfonyl tuted, a lower alkynyl group optionally Substituted, a higher group optionally substituted, an amino group Substituted with alkynyl group, an aromatic hydrocarbon group optionally an aromatic hydrocarbon group and optionally Substituted Substituted, a heterocyclic group optionally Substituted, with a lower alkyl group, anaromatic hydrocarbon oxy group, C(=O)CZ' (wherein, Z' is a lower alkyl group optionally a lower alkoxy group Substituted with at least one aromatic Substituted, a higher alkyl group, a lower cycloalkyl group hydrocarbon group, or a lower alkylidene amino group optionally Substituted, a lower alkenyl group optionally Sub optionally substituted with at least one aromatic hydrocarbon stituted, a higher alkenyl group, a lower cycloalkenyl group group. optionally Substituted, a lower alkynyl group optionally Sub 20. The compound according to 19, wherein stituted, a higher alkynyl group, an aromatic hydrocarbon 0187 X is OX', SX or S(O).X group optionally Substituted or a heterocyclic group option (wherein, X' represents an aromatic hydrocarbon group, ally substituted), SO.Z (wherein, Z is a lower alkyl group optionally substi (0188 X* is a lower alkyl group substituted with at least tuted, a higher alkyl group, a lower cycloalkyl group option one aromatic hydrocarbon group, a lower cycloalkyl group, ally substituted, a lower alkenyl group optionally Substituted, oran aromatic hydrocarbon group optionally Substituted with a higher alkenyl group, a lower cycloalkenyl group optionally at least one lower alkyl group or lower alkoxy group, Substituted, a lower alkynyl group optionally Substituted, a (0189 X is an aromatic hydrocarbon group), higher alkynyl group, an aromatic hydrocarbon group option 0.190 Y is SY ally Substituted, a heterocyclic group optionally substituted or (wherein, Y is an aromatic hydrocarbon group optionally an amino group optionally substituted), substituted with at least one substituent selected from the NZZ (wherein, Z and Z are each independently a hydro group consisting of (1) a halogen, (2) a lower alkyl group gen atom, a lower alkyl group optionally Substituted, a higher optionally Substituted with at least one halogen and (3) a alkyl group, a lower cycloalkyl group optionally Substituted, lower alkoxy group optionally substituted with at least one a lower alkenyl group optionally Substituted, a higher alkenyl halogen, or a heterocyclic group optionally substituted with group, a lower cycloalkenyl group optionally substituted, a one or more Substituent(s) selected from the group consisting lower alkynyl group optionally Substituted, a higher alkynyl of (1) a lower alkyl group optionally substituted with at least group, an aromatic hydrocarbon group optionally Substituted one halogen, and (2) a heterocyclic group Substituted with at or a heterocyclic group optionally Substituted, least one halogen), 0180 alternatively, are formed a ring structure together 0191 Z is a lower alkyl group substituted with at least one with the nitrogen which is bonded with each other), halogen; an aromatic hydrocarbon group optionally Substi OZ (wherein, Z is a lower alkyl group optionally substi tuted with one or more substituent(s) selected from the group tuted, a higher alkyl group, a lower cycloalkyl group option consisting of (1) a halogen, (2) a lower alkyl group and (3) a ally substituted, a lower alkenyl group optionally Substituted, lower alkoxy group; a lower alkoxycarbonyl group; an aro a higher alkenyl group, a lower cycloalkenyl group optionally matic hydrocarbon Sulfonyl group optionally Substituted; an Substituted, a lower alkynyl group optionally Substituted, a amino group Substituted with an aromatic hydrocarbon group higher alkynyl group, an aromatic hydrocarbon group option and optionally Substituted with a lower alkyl group; an aro ally Substituted or a heterocyclic group optionally Substi matic hydrocarbon oxy group; a lower alkoxy group Substi tuted), or tuted with at least one aromatic hydrocarbon group; or a lower N=C(Z)- (wherein, Z's are each independently a hydrogen alkylidene amino group Substituted with at least one aromatic atom, a lower alkyl group optionally Substituted, a higher hydrocarbon group. US 2011/0319437 A1 Dec. 29, 2011

21. The compound according to 15, wherein alkyl group, a lower cycloalkyl group optionally Substituted, (0192 X is OX', NXX, SX or S(O).X a lower alkenyl group optionally Substituted, a higher alkenyl (wherein, X" and X’ are a lower alkyl group optionally sub group, a lower cycloalkenyl group optionally substituted, a stituted, a higher alkyl group, a lower cycloalkyl group lower alkynyl group optionally Substituted, a higher alkynyl optionally Substituted, a lower alkenyl group optionally Sub group, an aromatic hydrocarbon group optionally Substituted stituted, a higher alkenyl group, a lower cycloalkenyl group or a heterocyclic group optionally Substituted, optionally Substituted, a lower alkynyl group optionally Sub 0199 alternatively, are formed a ring structure together stituted, a higher alkynyl group, an aromatic hydrocarbon with the nitrogen which is bonded with each other), group optionally Substituted, a heterocyclic group optionally OZ (wherein, Z is a lower alkyl group optionally substi substituted, C(=O)x" (wherein, Q'' is an oxygen atom, tuted, a higher alkyl group, a lower cycloalkyl group option and X' is a lower alkyl group optionally substituted), NX' ally substituted, a lower alkenyl group optionally Substituted, X' or N=C(X), a higher alkenyl group, a lower cycloalkenyl group optionally (0193 X and X are each independently a lower alkyl Substituted, a lower alkynyl group optionally Substituted, a group optionally substituted, a higher alkyl group, a lower higher alkynyl group, an aromatic hydrocarbon group option cycloalkyl group optionally substituted, a lower alkenyl ally Substituted or a heterocyclic group optionally Substi group optionally substituted, a higher alkenyl group, a lower tuted), or cycloalkenyl group optionally Substituted, a lower alkynyl N=C(Z) (wherein, Z's are each independently a hydrogen group optionally substituted, a higher alkynyl group, an aro atom, a lower alkyl group optionally Substituted, a higher matic hydrocarbon group optionally Substituted, a heterocy alkyl group, a lower cycloalkyl group optionally Substituted, clic group optionally substituted or C(=Q')X' (wherein, a lower alkenyl group optionally Substituted, a higher alkenyl Q’ is an oxygenatom, and X" is a lower alkyl group option group, a lower cycloalkenyl group optionally substituted, a ally substituted), lower alkynyl group optionally Substituted, a higher alkynyl (0194 X is a hydrogen atom, a lower alkyl group option group, an aromatic hydrocarbon group optionally Substituted ally Substituted, a higher alkyl group, a lower cycloalkyl or a heterocyclic group optionally Substituted, group optionally Substituted, a lower alkenyl group option ally substituted, a higher alkenyl group, a lower cycloalkenyl 0200 alternatively, are formed a ring structure together group optionally Substituted, a lower alkynyl group option with the carbon which is bonded with each other). ally Substituted, a higher alkynyl group, an aromatic hydro 22 The compound according to 21, wherein carbon group optionally substituted or a heterocyclic group 0201 X is SX optionally substituted, (wherein, X is a lower alkyl group optionally substituted, a (0195 alternatively, X and X are formed a ring structure lower cycloalkyl group optionally Substituted, an aromatic together with the nitrogen which is bonded with each other), hydrocarbon group optionally Substituted, or a heterocyclic 0196. Y is SY group optionally Substituted), (0197) (wherein, Y is a lower alkyl group optionally sub 0202 Y is SY stituted, a higher alkyl group, a lower cycloalkyl group (wherein, Y is a lower alkyl group optionally substituted, a optionally Substituted, a lower alkenyl group optionally Sub higher alkyl group, a lower cycloalkyl group optionally Sub stituted, a higher alkenyl group, a lower cycloalkenyl group stituted, a lower alkenyl group optionally substituted, a higher optionally Substituted, a lower alkynyl group optionally Sub alkenyl group, or a lower alkynyl group optionally Substi stituted, or a higher alkynyl group), tuted), 0198 Z is a lower alkyl group optionally substituted, a 0203 Z is an aromatic hydrocarbon group optionally Sub higher alkyl group, a lower cycloalkyl group optionally Sub stituted. stituted, a lower alkenyl group optionally substituted, a higher 23 The compound according to 22, wherein alkenyl group, a lower cycloalkenyl group optionally Substi tuted, a lower alkynyl group optionally Substituted, a higher 0204 X is SX alkynyl group, an aromatic hydrocarbon group optionally (wherein, X is a lower alkyl group optionally substituted Substituted, a heterocyclic group optionally Substituted, with at least one aromatic hydrocarbon group optionally Sub C(=O)CZ (wherein, Z is a lower alkyl group optionally stituted with one or more substituent (s) selected from the Substituted, a higher alkyl group, a lower cycloalkyl group group consisting of (1) a halogen, (2) a lower alkyl group and optionally Substituted, a lower alkenyl group optionally Sub (3) a lower alkoxy group; lower cycloalkyl group; an aromatic stituted, a higher alkenyl group, a lower cycloalkenyl group hydrocarbon group optionally Substituted with one or more optionally Substituted, a lower alkynyl group optionally Sub Substituent (s) selected from the group consisting of (1) a stituted, a higher alkynyl group, an aromatic hydrocarbon halogen, (2) a lower alkyl group optionally Substituted with at group optionally Substituted or a heterocyclic group option least one halogen, (3) a lower alkoxy group, and (4) a nitro ally substituted), group; or a heterocyclic group), SOZ (wherein, Z is a lower alkyl group optionally substi 0205 Y is SY tuted, a higher alkyl group, a lower cycloalkyl group option (wherein,Y is a lower alkyl group optionally substituted with ally substituted, a lower alkenyl group optionally Substituted, at least one substituent selected from the group consisting of a higher alkenyl group, a lower cycloalkenyl group optionally (1) an aromatic hydrocarbon group optionally Substituted Substituted, a lower alkynyl group optionally Substituted, a with at least one halogen and (2) a lower cycloalkyl group; a higher alkynyl group, an aromatic hydrocarbon group option higher alkyl group; a lower cycloalkyl group; a lower alkenyl ally Substituted, a heterocyclic group optionally substituted or group optionally Substituted with at least one halogen; a an amino group optionally substituted), higher alkenyl group; or a lower alkynyl group), NZZ (wherein, Z and Z are each independently a hydro 0206 Z is an aromatic hydrocarbon group optionally sub gen atom, a lower alkyl group optionally Substituted, a higher stituted with at least one lower alkyl group. US 2011/0319437 A1 Dec. 29, 2011

24. The compound according to 2, wherein SO.Z (wherein, Z is a lower alkyl group optionally substi 0207 X is OX', NXX, SX or S(O).X tuted, a higher alkyl group, a lower cycloalkyl group option (wherein, X and X’ are a lower alkyl group optionally sub ally substituted, a lower alkenyl group optionally Substituted, stituted, a higher alkyl group, a lower cycloalkyl group a higher alkenyl group, a lower cycloalkenyl group optionally optionally Substituted, a lower alkenyl group optionally Sub Substituted, a lower alkynyl group optionally Substituted, a stituted, a higher alkenyl group, a lower cycloalkenyl group higher alkynyl group, an aromatic hydrocarbon group option optionally Substituted, a lower alkynyl group optionally Sub ally Substituted, a heterocyclic group optionally substituted or stituted, a higher alkynyl group, an aromatic hydrocarbon an amino group optionally substituted), group optionally Substituted, a heterocyclic group optionally NZZ (wherein, Z and Z are each independently a hydro substituted, C(=Q')X' (wherein, Q is an oxygen atom, gen atom, a lower alkyl group optionally Substituted, a higher and X" is a lower alkyl group optionally substituted), NX' alkyl group, a lower cycloalkyl group optionally Substituted, X" or N=C(X), a lower alkenyl group optionally Substituted, a higher alkenyl 0208 X and X are each independently a lower alkyl group, a lower cycloalkenyl group optionally substituted, a group optionally substituted, a higher alkyl group, a lower lower alkynyl group optionally Substituted, a higher alkynyl cycloalkyl group optionally substituted, a lower alkenyl group, an aromatic hydrocarbon group optionally Substituted group optionally substituted, a higher alkenyl group, a lower or a heterocyclic group optionally Substituted, cycloalkenyl group optionally Substituted, a lower alkynyl 0214) alternatively, are formed a ring structure together with the nitrogen which is bonded with each other), group optionally substituted, a higher alkynyl group, an aro OZ (wherein, Z is a lower alkyl group optionally substi matic hydrocarbon group optionally Substituted, a heterocy tuted, a higher alkyl group, a lower cycloalkyl group option clic group optionally substituted or C(=Q')X' (wherein, ally substituted, a lower alkenyl group optionally Substituted, Q'' is an oxygenatom, and X" is a lower alkyl group option a higher alkenyl group, a lower cycloalkenyl group optionally ally substituted), Substituted, a lower alkynyl group optionally Substituted, a 0209 X is a hydrogen atom, a lower alkyl group option higher alkynyl group, an aromatic hydrocarbon group option ally Substituted, a higher alkyl group, a lower cycloalkyl ally Substituted or a heterocyclic group optionally Substi group optionally Substituted, a lower alkenyl group option tuted), or ally substituted, a higher alkenyl group, a lower cycloalkenyl N=C(Z) (wherein, Z's are each independently a hydrogen group optionally Substituted, a lower alkynyl group option atom, a lower alkyl group optionally Substituted, a higher ally Substituted, a higher alkynyl group, an aromatic hydro alkyl group, a lower cycloalkyl group optionally Substituted, carbon group optionally substituted or a heterocyclic group a lower alkenyl group optionally Substituted, a higher alkenyl optionally substituted, group, a lower cycloalkenyl group optionally substituted, a 0210 alternatively, X and X are formed a ring structure lower alkynyl group optionally Substituted, a higher alkynyl together with the nitrogen which is bonded with each other), group, an aromatic hydrocarbon group optionally Substituted 0211 Y is NY2Y or a heterocyclic group optionally Substituted, (wherein, Y is a lower alkyl group optionally substituted, a 0215 alternatively, are formed a ring structure together higher alkyl group, a lower cycloalkyl group optionally Sub with the carbon which is bonded with each other). stituted, a lower alkenyl group optionally substituted, a higher 25 The compound according to 24, wherein alkenyl group, a lower cycloalkenyl group optionally Substi 0216 X is SX tuted, a lower alkynyl group optionally Substituted, a higher (wherein, X is an aromatic hydrocarbon group optionally alkynyl group, an aromatic hydrocarbon group optionally substituted), Substituted, or a heterocyclic group optionally Substituted, 0217. Y is NY2Y 0212 Y is a hydrogen atom, a lower alkyl group option (wherein, Y is a lower alkyl group optionally substituted, and ally Substituted, a higher alkyl group, a lower cycloalkyl Y is a lower alkyl group optionally substituted, or an aro group optionally Substituted, a lower alkenyl group option matic hydrocarbon group optionally substituted), ally substituted, a higher alkenyl group, a lower cycloalkenyl 0218 Z is an aromatic hydrocarbon group optionally sub group optionally Substituted, a lower alkynyl group option stituted. ally Substituted, a higher alkynyl group, an aromatic hydro 26. The compound according to 25, wherein carbon group optionally Substituted, or a heterocyclic group 0219 X is SX optionally substituted), (wherein, X is an aromatic hydrocarbon group optionally 0213 Z is a lower alkyl group optionally substituted, a Substituted with at least one halogen or lower alkyl group), higher alkyl group, a lower cycloalkyl group optionally Sub 0220 Y is NYY stituted, a lower alkenyl group optionally substituted, a higher (wherein,Y is a lower alkyl group optionally substituted with alkenyl group, a lower cycloalkenyl group optionally Substi at least one aromatic hydrocarbon group, and Y is a lower tuted, a lower alkynyl group optionally Substituted, a higher alkyl group or an aromatic hydrocarbon group), alkynyl group, an aromatic hydrocarbon group optionally 0221 Z is an aromatic hydrocarbon group. Substituted, a heterocyclic group optionally Substituted, 27 The compound according to 2, wherein C(=O)CZ (wherein, Z is a lower alkyl group optionally 0222 X is OX', NXX, SX or S(O).X. Substituted, a higher alkyl group, a lower cycloalkyl group (wherein, X and X’ are a lower alkyl group optionally sub optionally Substituted, a lower alkenyl group optionally Sub stituted, a higher alkyl group, a lower cycloalkyl group stituted, a higher alkenyl group, a lower cycloalkenyl group optionally Substituted, a lower alkenyl group optionally Sub optionally Substituted, a lower alkynyl group optionally Sub stituted, a higher alkenyl group, a lower cycloalkenyl group stituted, a higher alkynyl group, an aromatic hydrocarbon optionally Substituted, a lower alkynyl group optionally Sub group optionally Substituted or a heterocyclic group option stituted, a higher alkynyl group, an aromatic hydrocarbon ally substituted), group optionally Substituted, a heterocyclic group optionally US 2011/0319437 A1 Dec. 29, 2011 substituted, C(=Q')X' (wherein, Q'' is an oxygen atom, group optionally Substituted, a lower alkynyl group option and X' is a lower alkyl group optionally substituted), NX' ally Substituted, an aromatic hydrocarbon group optionally X' or N=C(X), Substituted or a heterocyclic group optionally Substituted), 0223 X and X are each independently a lower alkyl NZZ (wherein, Z and Z are each independently a hydro group optionally substituted, a higher alkyl group, a lower gen atom, a lower alkyl group optionally Substituted, a lower cycloalkyl group optionally substituted, a lower alkenyl cycloalkyl group optionally substituted, a lower alkenyl group optionally substituted, a higher alkenyl group, a lower group optionally Substituted, a lower cycloalkenyl group cycloalkenyl group optionally Substituted, a lower alkynyl optionally Substituted, a lower alkynyl group optionally Sub group optionally substituted, a higher alkynyl group, an aro stituted, an aromatic hydrocarbon group optionally substi matic hydrocarbon group optionally Substituted, a heterocy tuted or a heterocyclic group optionally Substituted, clic group optionally substituted or C(=Q')X' (wherein, 0231 alternatively, are formed a ring structure together Q'' is an oxygenatom, and X" is a lower alkyl group option with the nitrogen which is bonded with each other), ally substituted), OZ (wherein, Z is a lower alkyl group optionally substi I0224 X is a hydrogen atom, a lower alkyl group option tuted, a lower cycloalkyl group optionally Substituted, a lower ally Substituted, a higher alkyl group, a lower cycloalkyl alkenyl group optionally substituted, a lower cycloalkenyl group optionally Substituted, a lower alkenyl group option group optionally Substituted, a lower alkynyl group option ally substituted, a higher alkenyl group, a lower cycloalkenyl ally Substituted, an aromatic hydrocarbon group optionally group optionally Substituted, a lower alkynyl group option Substituted or a heterocyclic group optionally Substituted), or ally Substituted, a higher alkynyl group, an aromatic hydro N=C(Z)- (wherein, Z's are each independently a hydrogen carbon group optionally substituted or a heterocyclic group atom, a lower alkyl group optionally Substituted, a lower optionally substituted, cycloalkyl group optionally substituted, a lower alkenyl 0225 alternatively, X and X are formed a ring structure group optionally Substituted, a lower cycloalkenyl group together with the nitrogen which is bonded with each other), optionally Substituted, a lower alkynyl group optionally Sub 0226 Y is OY, NY2Y or SY stituted, an aromatic hydrocarbon group optionally substi (wherein, Y is a lower alkyl group optionally substituted, a tuted or a heterocyclic group optionally Substituted, higher alkyl group, a lower cycloalkyl group optionally Sub 0232 alternatively, are formed a ring structure together stituted, a lower alkenyl group optionally substituted, a higher with the nitrogen which is bonded with each other). alkenyl group, a lower cycloalkenyl group optionally Substi 28. The compound according to 27, wherein tuted, a lower alkynyl group optionally Substituted, a higher 0233 X is OX', NXX, SX or S(O),X alkynyl group, an aromatic hydrocarbon group optionally (wherein, X is a lower alkyl group optionally substituted, an Substituted, a heterocyclic group optionally Substituted, or aromatic hydrocarbon group optionally substituted, a lower 0227 N=C(Y), cycloalkyl group optionally Substituted, a di-lower alkyl 0228 Y- and Y are each independently a lower alkyl amino group, a lower alkylidene amino group optionally Sub group optionally substituted, a higher alkyl group, a lower stituted or a lower cycloalkylidene amino group optionally cycloalkyl group optionally substituted, a lower alkenyl substituted, X is a lower alkyl group optionally substituted, group optionally substituted, a higher alkenyl group, a lower an aromatic hydrocarbon group optionally Substituted, or cycloalkenyl group optionally Substituted, a lower alkynyl C(=Q')X' (wherein, Q is an oxygen atom and X' is a group optionally substituted, a higher alkynyl group, an aro lower alkyl group optionally Substituted), matic hydrocarbon group optionally Substituted, or a hetero 0234 X is allower alkyl group optionally substituted oran cyclic group optionally Substituted, aromatic hydrocarbon group optionally Substituted, 0229. Y is a hydrogen atom, a lower alkyl group option 0235 X is a lower alkyl group optionally substituted, a ally Substituted, a higher alkyl group, a lower cycloalkyl higher alkyl group, a lower alkenyl group optionally Substi group optionally Substituted, a lower alkenyl group option tuted, a lower cycloalkyl group optionally substituted, an ally substituted, a higher alkenyl group, a lower cycloalkenyl aromatic hydrocarbon group optionally Substituted or a het group optionally Substituted, a lower alkynyl group option erocyclic group optionally substituted, and X is an aromatic ally Substituted, a higher alkynyl group, an aromatic hydro hydrocarbon group optionally Substituted), carbon group optionally Substituted, or a heterocyclic group 0236 Y is OY, NYY or SY optionally substituted), (wherein, Y is a lower alkyl group optionally substituted, an 0230 Z is a lower alkyl group optionally substituted, a aromatic hydrocarbon group optionally substituted, a hetero lower cycloalkyl group optionally Substituted, a lower alk cyclic group optionally substituted, or N=C(Y), (Y's are enyl group optionally Substituted, a lower cycloalkenyl group independently a lower alkyl group or an aromatic hydrocar optionally Substituted, a lower alkynyl group optionally Sub bon group), Y and Y are each independently a lower alkyl stituted, an aromatic hydrocarbon group optionally substi group optionally Substituted or an aromatic hydrocarbon tuted, a heterocyclic group optionally Substituted, group optionally substituted, and Y is a lower alkyl group C(=O)CZ' (wherein, Z' is a lower alkyl group optionally optionally Substituted, a higher alkyl group, a lower Substituted, a lower cycloalkyl group optionally Substituted, a cycloalkyl group optionally substituted, a lower alkenyl lower alkenyl group optionally Substituted, a lower cycloalk group optionally substituted, a higher alkenyl group, a lower enyl group optionally Substituted, a lower alkynyl group alkynyl group optionally Substituted, an aromatic hydrocar optionally Substituted, an aromatic hydrocarbon group bon group optionally Substituted or a heterocyclic group optionally substituted or a heterocyclic group optionally Sub optionally substituted), stituted), 0237 Z is a lower alkyl group optionally substituted, an SO.Z (wherein, Z is a lower alkyl group optionally substi aromatic hydrocarbon group optionally substituted, a hetero tuted, a lower cycloalkyl group optionally Substituted, a lower cyclic group optionally Substituted, a lower alkoxycarbonyl alkenyl group optionally substituted, a lower cycloalkenyl group, an aromatic hydrocarbon Sulfonyl group optionally US 2011/0319437 A1 Dec. 29, 2011

Substituted, an amino group Substituted with an aromatic (0245) Y is a lower alkyl group optionally substituted with hydrocarbon group and optionally Substituted with a lower at least one aromatic hydrocarbon group, or an aromatic alkyl group, and aromatic hydrocarbon oxy group, a lower hydrocarbon group, alkoxy group Substituted with at least one aromatic hydrocar 0246 Y is a lower alkyl group, bon group, or a lower alkylidene amino group optionally (0247 Y is a lower alkyl group optionally substituted with Substituted with at least one aromatic hydrocarbon group. one or more Substituent(s) selected from the group consisting 29. The compound according to 28, wherein of (1) an aromatic hydrocarbon group optionally Substituted 0238 X is OX', NXX, SX or S(O).X. with at least one halogen, (2) an aromatic hydrocarbon group (wherein, X is a lower alkyl group substituted with at least optionally substituted with at least one lower alkyl group and one aromatic hydrocarbon group optionally substituted with (3) a lower cycloalkyl group; a higher alkyl group; a lower one or more independent substituent(s) selected from the cycloalkyl group; an aromatic hydrocarbon group optionally group consisting of (1) a halogen, (2) a lower alkyl group and substituted with one or more independent substituent(s) (3) a lower alkoxy group; an aromatic hydrocarbon group selected from the group consisting of (1) a halogen, (2) a optionally substituted with one or more independent substitu lower alkyl group optionally Substituted with at least one ent(s) selected from the group consisting of (1) a halogen, (2) halogen, (3) a lower alkoxy group and (4) a lower haloalky a lower alkyl group optionally substituted with at least one loxy group; a heterocyclic group optionally Substituted with halogen, (3) a lower alkoxy group, (4) a lower alkoxycarbonyl one or more independent substituent(s) selected from the group, (5) a lower alkanoyl group, (6) a lower alkylthio group, group consisting of (1) a lower alkyl group, (2) a lower (7) an aromatic hydrocarbon group, (8) a cyano group, (9) a haloalkyl group and (3) a heterocyclic group Substituted with nitro group and (10) an alkylenedioxy group; a lower at least one halogen; a lower alkenyl group optionally Substi cycloalkyl group; an alkylidene amino group optionally Sub tuted with at least one halogen; a higher alkenyl group; or a stituted with at least one aromatic hydrocarbon group; a lower lower alkynyl group), cycloalkylidene amino group; or a di-lower alkyl amino 0248 Z is a lower alkyl group substituted with at least one grOup, halogen; an aromatic hydrocarbon group optionally Substi 0239 X is a lower alkyl group substituted with at least tuted with one or more independent substituent(s) selected one aromatic hydrocarbon group, an aromatic hydrocarbon from the group consisting of (1) a halogen, (2) a cyano group, group, or a lower alkanoyl group, (3) a hydroxy group, (4) a lower alkyl group optionally Sub 0240 X is a lower alkyl group or an aromatic hydrocar stituted with at least one halogen or aromatic hydrocarbon bon group, group, (5) a lower alkenyl group, (6) a lower alkoxy group 0241) alternatively, X and X are formed a piperidino optionally substituted with at least one halogen, (7) a lower group or a morpholino group together with the nitrogen alkanoyl oxy group, (8) an aromatic hydrocarbon group which is bonded with each other, optionally substituted with at least one alkyl or halogen, (9) a 0242 X is an aromatic hydrocarbon group optionally heterocyclic group, (10) a lower alkylthio group, (11) a lower substituted with one or more independent substituent(s) alkylsulfinyl group, (12) a lower alkylsulfonyl group, (13) an selected from the group consisting of (1) a halogen, (2) a arylthio group, (14) a lower alkoxy carbonyl group, (15) a lower alkyl group and (3) a lower alkoxy group; a lower alkyl lower alkanoyl group, (16) anaromatic hydrocarbon carbonyl group optionally substituted with at least one heterocyclic group, (17) a lower alkynyl group, (18) a lower cycloalkylthio group optionally Substituted with at least one halogen; a group, (19) a lower alkylenedioxy group, (20) a lower alky higher alkyl group; a lower alkenyl group; a lower cycloalkyl lene group and (21) a nitro group; a heterocyclic group; a group; an aromatic hydrocarbon group optionally Substituted lower alkoxycarbonyl group; an aromatic hydrocarbon Sulfo with one or more independent substituent(s) selected from the nyl group; an amino group Substituted with an aromatic group consisting of (1) a halogen, (2) a nitro group, (3) a lower hydrocarbon group and optionally Substituted with a lower alkyl group, (4) a halo-lower alkyl group, and (5) a lower alkyl group; an aromatic hydrocarbon oxy group; a lower alkoxy group; or a heterocyclic group optionally Substituted alkoxy group Substituted with at least one aromatic hydrocar with one or more lower alkyl group(S), bon group, or a lower alkylidene amino group Substituted 0243 X is an aromatic hydrocarbon group), with at least one aromatic hydrocarbon group. 0244 Y is OY, NYY or SY 30 The compound according to 2, wherein (wherein, Y is a lower alkyl group optionally substituted with 0249 X is OX', NXX, SX or S(O).X. one or more Substituent(s) selected from the group consisting (wherein, X" is a lower alkyl group optionally substituted, an of (1) an aromatic hydrocarbon group optionally Substituted aromatic hydrocarbon group optionally substituted, a lower with at least one lower alkyl group, (2) an aromatic hydrocar cycloalkyl group optionally Substituted, a di-lower alky bon group Substituted with at least one halogen and (3) a lamino group, a lower alkylidene amino group optionally heterocyclic group Substituted with at least one halogen; an Substituted or a lower cycloalkylidene amino group option aromatic hydrocarbon group optionally Substituted with one ally substituted, or more independent Substituent(s) selected from the group (0250 X is a lower alkyl group optionally substituted, an consisting of (1) a halogen, (2) a cyano group, (3) a nitro aromatic hydrocarbon group optionally Substituted or group, (4) a lower alkyl group, (5) anamino group, (6) a lower C(=Q')X' (wherein, Q is an oxygen atom and X' is a alkylthio group, (7) a lower alkylsulfonyl group, (8) a lower lower alkyl group optionally Substituted), cycloalkyl group, (9) an aromatic hydrocarbon group, (10) a (0251 X is allower alkyl group optionally substituted oran lower alkoxycarbonyl group, (11) a lower alkoxy group, (12) aromatic hydrocarbon group optionally Substituted, a heterocyclic group, (13) a lower alkylene group and (14) a 10252 X is a lower alkyl group optionally substituted, a lower alkylenedioxy group; a heterocyclic group; or a lower higher alkenyl group, a lower alkyl group optionally Substi alkylidene amino group optionally Substituted at least one tuted, a lower cycloalkyl group optionally substituted, an aromatic hydrocarbon group, aromatic hydrocarbon group optionally Substituted or a het US 2011/0319437 A1 Dec. 29, 2011 erocyclic group optionally substituted, X is an aromatic cyclic group optionally substituted, or N=C(Y), (Y's are hydrocarbon group optionally Substituted), independently a lower alkyl group or an aromatic hydrocar 0253 Y is OY, NYY or SY bon group, (wherein, Y is a lower alkyl group optionally substituted, an 10263 Y is a lower alkyl group optionally substituted with aromatic hydrocarbon group optionally substituted, a hetero at least one aromatic hydrocarbon group, cyclic group optionally substituted, or N=C(Y), (Y's are 0264. Y is a lower alkyl group or an aromatic hydrocar independently a lower alkyl group or an aromatic hydrocar bon group, bon group, 10265 Y is a lower alkyl group optionally substituted with (0254 Y is an aromatic hydrocarbon group optionally one or more Substituent(s) selected from the group consisting substituted, of (1) an aromatic hydrocarbon group optionally Substituted (0255 Y is a lower alkyl group optionally substituted oran with at least one halogen and (2) a lower cycloalkyl group; a aromatic hydrocarbon group optionally Substituted, higher alkyl group; a lower cycloalkyl group; a lower alkenyl 0256 Y is a lower alkyl group optionally substituted, a group optionally Substituted with at least one halogen; a higher alkyl group, a lower cycloalkyl group optionally Sub higher alkenyl group; a lower alkynyl group; an aromatic stituted, a lower alkenyl group optionally substituted, a higher hydrocarbon group optionally Substituted with one or more alkenyl group, a lower alkynyl group optionally Substituted, Substituent (s) selected from the group consisting of (1) a an aromatic hydrocarbon group optionally substituted or a halogen, (2) a lower alkyl group optionally Substituted with at heterocyclic group optionally Substituted), least one halogen and a lower alkoxy group optionally Sub 0257 Z is a lower alkyl group optionally substituted, an stituted with at least one halogen; or a heterocyclic group aromatic hydrocarbon group optionally substituted, a hetero optionally substituted with one or more substituent selected cyclic group optionally substituted, a lower alkoxycarbonyl from the group consisting of (1) a lower alkyl group option group, an aromatic hydrocarbon Sulfonyl group optionally ally Substituted with at least one halogen and (2) a heterocy Substituted, an amino group Substituted with an aromatic clic group Substituted with at least one halogen), hydrocarbon group and optionally Substituted with a lower 0266 Z is a lower alkyl group substituted with at least one alkyl group, an aromatic hydrocarbon oxy group, a lower halogen; an aromatic hydrocarbon group optionally Substi alkoxy group Substituted with at least one aromatic hydrocar tuted with one or more independent substituent(s) selected bon group, or a lower alkylidene amino group optionally from the group consisting of (1) a halogen, (2) a cyano group, Substituted with at least one aromatic hydrocarbon group. (3) a hydroxy group, (4) a lower alkyl group optionally Sub 31 The compound according to 30, wherein stituted with at least one halogen or aromatic hydrocarbon 0258 X is OX', NXX, SX or S(O).X. group, (5) a lower alkenyl group, (6) a lower alkoxy group (wherein, X is a lower alkyl group substituted with at least optionally substituted with at least one halogen, (7) a lower one aromatic hydrocarbon group optionally substituted with alkanoyl oxy group, (8) an aromatic hydrocarbon group one or more independent substituent(s) selected from the optionally substituted with at least one alkyl or halogen, (9) a group consisting of (1) a halogen, (2) a lower alkyl group and heterocyclic group, (10) a lower alkylthio group, (11) a lower (3) a lower alkoxy group; or an aromatic hydrocarbon group alkylsulfinyl group, (12) a lower alkylsulfonyl group, (13) an optionally substituted with one or more independent substitu arylthio group, (14) a lower alkoxy carbonyl group, (15) a ent(s) selected from the group consisting of (1) a halogen, (2) lower alkanoyl group, (16) anaromatic hydrocarbon carbonyl a lower alkyl group optionally substituted with at least one group, (17) a lower alkynyl group, (18) a lower cycloalkylthio halogen, (3) a lower alkoxy group, (4) a lower alkoxycarbonyl group, (19) a lower alkylene dioxy group, (20) a lower alky group, (5) a lower alkylthio group, (6) an aromatic hydrocar lene group and (21) a nitro group; a heterocyclic group; a bon group, (7) a cyano group, (8) a nitro group and (9) an lower alkoxycarbonyl group; an aromatic hydrocarbon Sulfo alkylenedioxy group, nyl group; an amino group Substituted with an aromatic 0259 X is a lower alkyl group substituted with at least hydrocarbon group and optionally Substituted with a lower one aromatic hydrocarbon group, an aromatic hydrocarbon alkyl group; an aromatic hydrocarbon oxy group; a lower group, or a lower alkanoyl group, alkoxy group Substituted with at least one aromatic hydrocar 0260 X is a lower alkyl group or an aromatic hydrocar bon group; or a lower alkylidene amino group Substituted bon group, with at least one aromatic hydrocarbon group. 0261) X* is a lower alkyl group optionally substituted with 32 The compound according to 1, wherein one or more Substituent(s) selected from the group consisting 0267 X is phenylthio group optionally substituted with at of (1) an aromatic hydrocarbon group optionally Substituted least one Substituent selected from the group consisting of a with at least one halogen or lower alkyl group and (2) a halogen, a methyl group, a trifluoromethyl group and a meth heterocyclic group Substituted with at least one halogen; a oxy group; or phenoxy group optionally substituted with at higher alkyl group; a lower alkenyl group; a lower cycloalkyl least one Substituent selected from the group consisting of a group; an aromatic hydrocarbon group optionally Substituted halogen, a methyl group, a trifluoromethyl group and a meth with one or more independent substituent(s) selected from the OXy group: group consisting of (1) a halogen, (2) a nitro group, (3) a lower 0268 Y is phenylthio group optionally substituted with at alkyl group, (4) a lower haloalkyl group and (5) a lower least one Substituent selected from the group consisting of a alkoxy group; or a heterocyclic group optionally Substituted halogen, a methyl group, a trifluoromethyl group and a meth with one or more substituent(s), and X is an aromatic hydro oxy group; phenoxy group optionally substituted with at least carbon group), one Substituent selected from the group consisting of a halo 0262 Y is OY, NY2Y or SY gen, a methyl group, a trifluoromethyl group and a methoxy (wherein, Y is a lower alkyl group optionally substituted, an group; a benzylthio group optionally substituted with at least aromatic hydrocarbon group optionally substituted, a hetero one Substituent selected from the group consisting a halogen, US 2011/0319437 A1 Dec. 29, 2011 and a methyl group; sec-butylthio group; cyclohexylmeth m' is 2, two Xs may be the same or different, and Z' ylthio group; or cyclohexylthio group: represents a halogen atom, C alkyl group, Chaloalkyl 0269 Z is phenyl group optionally substituted with at least group or Calkoxy group, and when n' is 2, two Zs may be one Substituent selected from the group consisting of a halo the same or different.). gen, a methyl group, an isopropyl group, a trifluoromethyl AB2 The iminopropene compound according to AB1 group and a methoxy group. wherein in the formula (ABI), R" represents a Co 33. The compound according to 1, wherein branched alkyl group. 0270 X is phenylthio group optionally substituted with at AB3. The iminopropene compound according to AB1 least one Substituent selected from the group consisting of a wherein in the formula (ABI), R“represents a C79 branched halogen, a methyl group, a trifluoromethyl group and a meth alkyl group. oxy group; or phenoxy group optionally substituted with at AB4 The iminopropene compound according to AB1 least one Substituent selected from the group consisting of a wherein in the formula (ABI). R' represents a 3 to 6-mem halogen, a methyl group, a trifluoromethyl group and a meth bered cycloalkyl group Substituted by at least one C alkyl OXy group: group. 0271 Y is phenylthio group optionally substituted with at AB5. The iminopropene compound according to AB1 least one Substituent selected from the group consisting of a wherein in the formula (ABI), R" represents a cyclohexyl halogen, a methyl group, a trifluoromethyl group and a meth group Substituted by at least one C alkyl group. oxy group; phenoxy group optionally substituted with at least AB6 The iminopropene compound according to AB1 one Substituent selected from the group consisting of a halo wherein in the formula (ABI), R" represents a 3 to 6-mem gen, a methyl group, a trifluoromethyl group and a methoxy bered cycloalkyl group condenced with benzene ring. group; or cyclohexylthio group: 0273 Suitable examples and actual examples of various 0272 Z is phenyl group optionally substituted with at least definitions included the present invention used in the above one Substituent selected from the group consisting of a halo and following descriptions of the instant specification will be gen, a methyl group, an isopropyl group, a trifluoromethyl described in detail below. group and a methoxy group. 0274 The term “lower” means a group having 6 or less AA1 An iminopropene compound of the formula (AAI): carbon atoms, unless otherwise stated. 0275. The term “higher means a group having 7 to 20 carbon atoms, unless otherwise stated. (AAI) 0276 Suitable examples of “one or more' may include 1 to 6, preferably 1 to 3. Y 0277 Suitable examples of “lower alkyl group” in the term “lower alkyl group optionally substituted”, “lower alkyl ( )-s-ch=ch group' and “lower alkyl include linear or branched C. (X44)2.41. alkyl groups, for example, methyl, ethyl, n-propyl, isopropyl. n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, Sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl and the like. (wherein, R' represents a Calkyl group substituted with a 0278 Suitable examples of “higher alkyl group' include C. cycloalkyl group, m' represents an integer of 0 to 2, n' linear or branched C-2 alkyl groups, for example, heptyl, represents an integer of 0 to 2.X' represents a halogenatom, octyl, 3,5-dimethyloctyl, 3,7-dimethyloctyl, nonyl, decyl, Cs alkyl group, C-shaloalkyl group, Calkoxy group or undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, heptadecyl. nitro group, and when m' is 2, two Xs may be the same or octadecyl, nonadecyl, icosyl and the like. different, and Z' represents a halogen atom, C.s haloalkyl 0279 Suitable examples of “lower alkenyl group' in the group or Calkoxy group, and when n' is 2, two Zs may be term “lower alkenyl group optionally substituted” and “lower the same or different.). alkenyl group” include linear or branched C- alkenyl AA2 The iminopropene compound according to AA1 groups, for example, vinyl, allyl, isopropenyl, isobutenyl, wherein in the formula (AAI), Z' represents a halogenatom 1-methylallyl, 3-methyl-2-butenyl, 2-pentenyl, 2-hexenyl or Calkoxy group. and the like. AB1 An iminopropene compound of the formula (ABI): 0280 Suitable examples of “higher alkenyl group' include linear or branched Cz-oalkenyl groups, for example, heptenyl, octenyl, 3,5-dimethyloctenyl, 3,7-dimethyl-6-octe (ABI) nyl, geranyl and the like. Y RAB 0281 Suitable examples of “lower alkynyl group' in the term “lower alkynyl group optionally substituted” and “lower S-CHECH-C N alkynyl group” include C. alkynyl groups, for example, 1 n(ZABAB ethynyl, propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3-hexy nyl and the like. 0282 Suitable examples of “higher alkynyl group' (wherein, R" represents a Cobranched alkyl group, or a 3 include linear or branched C-2 alkynyl groups, for example, to 6-membered cycloalkyl group Substituted by at least one heptynyl, octynyl, 3,5-dimethyloctynyl 3,7-dimethyloctynyl Cls alkyl group or condenced with benzene ring, m' repre and the like. sents an integer of 0 to 2, n' represents an integer of 0 to 2, 0283 Suitable examples of “lower cycloalkyl group' in X' represents a halogen atom, C- alkyl group, Cls the term “lower cycloalkyl group optionally substituted” and haloalkyl group, Calkoxy group or nitro group, and when “lower cycloalkyl group' include C. cycloalkyl groups, for US 2011/0319437 A1 Dec. 29, 2011 example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl unsaturated condensed heterocyclic groups containing one or and the like, and preferably may be C. cycloalkyl groups, two Sulfur atoms and containing 1 to 3-nitrogen atoms, for most preferably cyclohexyl. example, benzothiazolyl, benzothiadiazolyl, imidazothiadia 0284 Suitable examples of “lower cycloalkenyl group' in Zolyl and the like; unsaturated 3 to 8-membered (more pref the term “lower cycloalkenyl group optionally substituted erably, 5 to 6-membered) heteromonocyclic groups contain and “lower cycloalkenyl group' include Cecycloalkenyl ing one or two oxygen atoms, for example, furyl, groups, for example, cyclopropenyl, cyclobutenyl, cyclopen dihydropyranyl, dioxynyl and the like: saturated 3 to 8-mem tenyl, cyclohexenyl (e.g., 2-cyclohexen-1-yl, 3-cyclohexen bered (more preferably, 5 to 6-membered) heteromonocyclic 1-yl) and the like, and this “lower cycloalkenyl' may have a groups containing one or two oxygen atoms, for example, lower alkyl. tetrahydrofuryl, tetrahydropyranyl, dioxanyl and the like: 0285 Suitable examples of “aromatic hydrocarbon unsaturated condensed heterocyclic groups containing one or group' in the term 'aromatic hydrocarbon group optionally two oxygen atoms, for example, benzofuryl, benzodioxola substituted”, “aromatic hydrocarbon group' and “aryl' nyl, benzodioxanyl and the like; unsaturated 3 to 8-membered include, for example, phenyls optionally having at least one (more preferably, 5 to 6-membered) heteromonocyclic lower alkyl group (e.g., phenyl, mesity1, Xylyl, tolyl and the groups containing an oxygen atom and one or two Sulfur like) and Cea aromatic hydrocarbon groups such as naph atoms, for example, dihydroxathiinyl and the like; unsatur thyl, anthryl, indanyl, tetrahydronaphthyl and the like, and ated condensed heterocyclic groups containing one or two preferably may be phenyl and naphthyl, and this “aromatic sulfur atoms, for example, benzothienyl, benzodithiinyl and hydrocarbon group' may have a Suitable Substituent Such as a the like; unsaturated condensed heterocyclic groups contain lower alkyl, a halogen, a lower alkoxy group, a lower ing an oxygenatom and one or two Sulfur atoms, for example, cycloalkyl group and the like. benzoxathiinyl and the like; and this "heterocyclic group' and "heterocyclic' part may have at least one suitable substituent 0286 Suitable examples of "heterocyclic group' in the Such as a lower alkyl, a halogen, a lower alkoxy group or a term "heterocyclic group optionally substituted, and “het lower cycloalkyl group and the like. erocyclic' part include unsaturated 3 to 8-membered (more preferably, 5 to 6-membered) heteromonocyclic groups con 0287 Halogen represents fluorine, chlorine, bromine or taining 1 to 4 nitrogen atoms, for example, pyrrolyl pyrroly iodine. nyl, imidazolyl pyrazolyl pyridyl, dihydropyridyl, pyrim 0288 Suitable examples of “lower haloalkyl group' idyl, pyrazinyl, pyridazinyl, triazolyl (e.g., 4H-1,2,4- include fluoromethyl, difluoromethyl, trifluoromethyl, chlo triazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyland the like), romethyl, pentafluoroethyl and the like. tetrazolyl (e.g., 1H-tetrazolyl, 2H-tetrazolyland the like), and 0289 Suitable examples of “lower alkoxy group' in the the like: saturated 3 to 8-membered (more preferably, 5 to term “lower alkoxy group optionally substituted”, “lower 6-membered) heteromonocyclic groups containing 1 to 4 alkoxy group' and “lower alkoxy' include linear or branched nitrogen atoms, for example, pyrrolydinyl, imidazolydinyl, Calkoxy groups, for example, methoxy, ethoxy, propoxy, piperidyl, piperidino, piperadinyl and the like; unsaturated isopropoxy, butoxy, isobutoxy, tet-butoxy, pentyloxy, tert condensed heterocyclic groups containing 1 to 4 nitrogen pentyloxy, neo-pentyloxy, hexyloxy, isohexyloxy and the atoms, for example, indolyl, isoindolyl, indolinyl, indolidi like, preferably, methoxy, ethoxy, propoxy, butoxy, penty nyl, benzimidazolyl, quinolyl, isoquinolyl, indazolyl, benzo loxy, hexyloxy and isohexyloxy. triazolyl, imidazopyridinyl, imidazothiazolyl and the like; 0290 Suitable examples of “lower cycloalkyloxy group' unsaturated 3 to 8-membered (more preferably, 5 to 6-mem in the term “lower cycloalkyloxy group optionally Substi bered) heteromonocyclic groups containing one or two oxy tuted and “lower cycloalkyloxy group” include C. gen atoms and 1 to 3 nitrogen atoms, for example, oxazolyl, cycloalkyloxy groups such as cyclopropyloxy, cyclobuty isoxazolyl, oxadiazolyl (e.g., I,2,4-oxadiazolyl, 1,3,4-oxa loxy, cyclopentyloxy, cyclohexyloxy and the like. diazolyl. I,2,5-oxadiazolyl and the like), and the like; Satu 0291 “Acyl group' and “acyl include aliphatic acyl, aro rated 3 to 8-membered (more preferably, 5 to 6-membered) matic acyl, aryl aliphatic acyl, heterocyclic acyl and hetero heteromonocyclic groups containing one or two oxygen cyclic aliphatic acyl derived from a carboxylic acid, carbonic atoms and 1 to 3 nitrogen atoms, for example, morpholinyl, acid, carbamic acid, Sulfonic acid and the like. morpholino and the like; unsaturated condensed heterocyclic 0292 Suitable examples of the above-mentioned “acyl groups containing one or two oxygenatoms and 1 to 3 nitro group' include those described below. gen atoms, for example, benzoxazolyl, benzoxadiazolyl and 0293 carboxy; carbamoyl: mono or di-lower alkylcar the like; unsaturated 3 to 8-membered (more preferably, 5 to bamoyl (e.g., methylcarbamoyl, dimethylcarbamoyl, ethyl 6-membered) heteromonocyclic groups containing one or carbamoyl, diethylcarbamoyl and the like), mono or diaryl two Sulfur atoms and 1 to 3 nitrogen atoms, for example, carbamoyl (e.g., phenylcarbamoyl, diphenylcarbamoyl and thiazolyl, isothiazolyl, thiadiazolyl (e.g., 1,2,3-thiadiazolyl, the like); lower alkylaryl carbamoyl (e.g., methylphenylcar I,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, I,2,5-thiadiazolyl and bamoyl and the like); thiocarbamoyl: mono or di-lower alky the like), and dihydrothiazinyl and the like: saturated 3 to lthiocarbamoyl (e.g., methylthiocarbamoyl, dimethylthiocar 8-membered (more preferably, 5 to 6-membered) hetero bamoyl, ethylthiocarbamoyl, diethylthiocarbamoyl and the monocyclic groups containing one or two Sulfur atoms and 1 like); mono or diarylthiocarbamoyl (e.g., phenylthiocarbam to 3 nitrogenatoms, for example, thiazolidinyl, thiomorpholi oyl, diphenylthiocarbamoyl and the like); lower alkylarylth nyl, thiomorpholino and the like; unsaturated 3 to 8-mem iocarbamoyl (e.g., methylphenylthiocarbamoyland the like); bered (more preferably, 5 to 6-membered) heteromonocyclic 0294 aliphatic acyl, groups containing one or two Sulfur atoms, for example, 0295 for example, lower alkanoyl (e.g., C alkanoyl thienyl, dihydrodithiinyl, dihydrodithionyl and the like: satu groups such as formyl, acetyl, propanoyl, butanoyl, 2-meth rated heteromonocyclic groups containing one or two Sulfur ylpropanoyl, pentanoyl, 2.2-dimethylpropanoyl, hexanoyl atoms, for example, tetrahydrothienyl, dithianyl and the like; and the like); higher alkanoyl (e.g., C. alkanoyl groups US 2011/0319437 A1 Dec. 29, 2011 20

Such as heptanoyl, octanoyl, nonanoyl, decanoyl, unde neaminoxy, propylideneaminoxy, isopropylideneaminoxy, canoyl, dodecanoyl, tridecanoyl, tetradecanoyl, pentade cyclohexylideneaminoxy and the like). canoyl, hexadecanoyl, heptadecanoyl, octadecanoyl, nonade 0302 Suitable examples of “lower alkylidenehydrazino canoyl, icosanoyl and the like); lower alkoxycarbonyl (e.g., group' include C. alkylidenehydrazino groups (e.g., eth C. alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, butoxycarbonyl, t-bu ylidenehydrazino, propylidenehydrazino, isopropylidenehy toxycarbonyl, t-pentyloxycarbonyl, hexyloxycarbonyl and drazino, cyclohexylidenehydrazino and the like). the like); higher alkoxycarbonyl (e.g., C. alkoxycarbonyl 0303 Suitable examples of “lower alkylidenehydrazono groups such as heptyloxycarbonyl, octyloxycarbonyl, nony group' include C. alkylidenehydrazono groups (e.g., eth loxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and ylidenehydrazono, propylidenehydrazono, isopropylidene the like); lower alkylsulfonyl (e.g., C alkylsulfonyl groups hydrazono, cyclohexylidenehydrazono and the like). Such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso 0304 Suitable examples of “lower alkanoyloxy group' propylsulfonyl. n-butylsuofonyl, tert-butylsulfonyl, n-pen include Calkanoyloxy groups (e.g., formyloxy, acetyloxy, tylsulfonyl, hexylsulfonyl and the like); higher alkylsulfonyl propanoyloxy, butanoyloxy, 2-methylpropanoyloxy, pen (e.g., Cz-o alkylsulfonyl groups such as heptylsulfonyl, tanoyloxy, 2,2-dimethylpropanoyloxy, hexanoyloxy and the octylsulfonyl, nonylsulfonyl, decylsulfonyl, dodecylsulfo like). nyl, pentadecylsulfonyl and the like); lower alkoxysulfonyl (e.g., C alkoxysulfonyl groups such as methoxysulfonyl, (0305 Suitable examples of “lower alkylthio group” ethoxysulfonyl, propoxysulfonyl, butoxysulfonyl, tert-bu include Calkylthiogroups (e.g., methylthio, ethylthio, pro toxysulfonyl, pentyloxysulfonyl, hexyloxysulfonyl and the pylthio and the like). like); higher alkoxysulfonyl (e.g., C. alkoxysulfonyl 0306 Suitable examples of “lower alkylsulfinyl group' groups such as heptyloxysulfonyl, octyloxysulfonyl, nony include C. alkylsulfinyl groups (e.g., methylsulfinyl group, loxysulfonyl, decyloxysulfonyl, undecyloxysulfonyl and the ethylsulfinyl group, propylsulfinyl group and the like). like): 0307 Suitable examples of “lower alkylsulfonyl group' 0296 aromatic acyl, include C. alkylsulfonyl groups (e.g., methylsulfonyl 0297 for example, aroyl (e.g., benzoyl, toluoyl, naphthoyl group, ethylsulfonyl group, propylsulfonyl group and the and the like), aryllower alkanoyl (e.g., phenyl (Ce) alkanoyl like). groups such as phenylacetyl, phenylpropanoyl phenylbu 0308 Suitable examples of “arylthio group' include a tanoyl phenylisobutanoyl phenylpentanoyl phenylhex phenylthio group, mesitylthio group, Xylylthio group, anoyl and the like, naphthyl (Ce) alkanoyl groups such as tolylthio group, naphthylthio group and the like. naphthylacetyl, naphthylpropanoyl, naphthylbutanoyl and (0309. In the compound (I), X represents OX', NXX, the like); aryl lower alkenoyl (e.g., phenyl (C) alkenoyl SX, S(O).X, Si(X) or N=C(X7). groups such as phenylpropenoyl phenylbutenoyl phenyl 0310. X" represents a lower alkyl group optionally substi methacryloyl phenylpentenoyl phenylhexenoyland the like, tuted, a higher alkyl group, a lower cycloalkyl group option naphthyl (C) alkenoyl groups such as naphthylpropenoyl. ally substituted, a lower alkenyl group optionally Substituted, naphthylbutenoyl and the like); aryl lower alkoxycarbonyl a higher alkenyl group, a lower cycloalkenyl group optionally (e.g., phenyl (Ce) alkoxycarbonyl groups such as benzy Substituted, a lower alkynyl group optionally Substituted, a loxycarbonyl and the like, fluorenyl (Ce) alkoxycarbonyl higher alkynyl group, an aromatic hydrocarbon group option groups such as fluorenylmethyloxycarbonyl and the like); ally substituted, a heterocyclic group optionally Substituted, aryloxycarbonyl (e.g., phenoxycarbonyl, naphthyloxycarbo C(—Q'')X', C(=O)CX', C(-Q12)NXPX-1, SOX', nyl and the like); aryloxy lower alkanoyl (e.g., phenoxy NXX or N CCX), acetyl, phenoxypropionyl and the like); arylglyoxyloyl (e.g., 0311 and preferably mentioned is a lower alkyl group phenylglyoxyloyl, naphthylglyoxyloyland the like); arylsul optionally substituted or an aromatic hydrocarbon group fonyl optionally having 1 to 4 lower alkyls (e.g., phenylsul optionally substituted, and particularly preferably mentioned fonyl, p-tolylsulfonyl and the like) and the like; and is a lower alkyl group Substituted with at least one aromatic 0298 heterocyclic acyl hydrocarbon group or an aromatic hydrocarbon group option 0299 for example, heterocyclic carbonyl; heterocyclic ally substituted. lower alkanoyl (e.g., heterocyclic (C) alkanoyl groups such as heterocyclic acetyl, heterocyclic propanoyl, heterocyclic 0312 For the above-mentioned “lower alkyl group' in the butanoyl, heterocyclic pentanoyl, heterocyclic hexanoyl and term “lower alkyl group optionally substituted” for X', the the like); heterocyclic lower alkenoyl (e.g., heterocyclic (C- “lower alkyl group' described above can be referred to. 6) alkenoyl groups such as heterocyclic propenoyl, heterocy 0313 For the above-mentioned “higher alkyl group' for clic butenoyl, heterocyclic pentenoyl, heterocyclic hexenoyl X', the “higher alkyl group' described above can be referred and the like); heterocyclic glyoxyloyl and the like. Here, for tO suitable "heterocyclic' part in the terms "heterocyclic carbo 0314 For the above-mentioned “lower cycloalkyl group' nyl', "heterocyclic lower alkanoyl, "heterocyclic lower alk in the term “lower cycloalkyl group optionally substituted enoyland "heterocyclic glyoxyloyl, the "heterocyclic' part for X', the “lower cycloalkyl group' described above can be described above can be referred to. referred to. 0300 Suitable examples of “lower alkylideneamino 0315 For the above-mentioned “lower alkenyl group' in group' include C alkylideneaminoxy groups (e.g., eth the term “lower alkenyl group optionally substituted for X', ylideneamino, propylideneamino, isopropylideneamino, the “lower alkenyl group' described above can be referred to. cyclohexylideneamino and the like). 0316 For the above-mentioned “higher alkenyl group' for 0301 Suitable examples of “lower alkylideneaminoxy X', the “higher alkenyl group” described above can be group' include C alkylideneamino groups (e.g., ethylide referred to. US 2011/0319437 A1 Dec. 29, 2011

0317 For the above-mentioned “lower cycloalkenyl 0339. Here, X' and X' represent each independently a group' in the term “lower cycloalkenyl group optionally Sub lower alkyl group, a lower cycloalkyl group, a lower alkenyl stituted” for X', the “lower cycloalkenyl group” described group, a lower cycloalkenyl group, a lower alkynyl group, an above can be referred to. aromatic hydrocarbon group or a heterocyclic group, and 0318 For the above-mentioned “lower alkynyl group' in Q', Q' and Q' represent each independently an oxygen the term “lower alkynyl group optionally substituted” for X', atom or a Sulfur atom. the “lower alkynyl group' described above can be referred to. (0340 When the substituent in the terms “lower alkyl 0319 For the above-mentioned “higher alkynyl group' for group optionally Substituted”. “lower cycloalkyl group X', the "higher alkynyl group” described above can be optionally substituted”, “lower alkenyl group optionally sub referred to. stituted”, “lower cycloalkenyl group optionally substituted 0320 For the above-mentioned “aromatic hydrocarbon and “lower alkynyl group optionally Substituted” is an acyl group' in the term 'aromatic hydrocarbon group optionally group. C. alkylideneamino group, C-alkylideneaminoxy substituted” for X', the 'aromatic hydrocarbon group” group, Calkylidenehydrazino group or C. alkylidenehy described above can be referred to. drazono group, 0321 For the above-mentioned "heterocyclic group” in 0341 or, when one or more of X', X', X, XP, X', the term "heterocyclic group optionally substituted” for X', X1, X1, X1, X1, X1,X^, XII, XI and X19 are a lower the "heterocyclic group' described above can be referred to. alkyl group, a lower cycloalkyl group, a lower alkenyl group, 0322 Suitable examples of substituents in the terms “lower alkyl group optionally substituted”, “lower cycloalkyl a lower cycloalkenyl group or a lower alkynyl group, group optionally Substituted”. “lower alkenyl group option 0342 these groups maybe further substituted with a nitro ally substituted”, “lower cycloalkenyl group optionally sub group, a cyano group, a carboxyl group, a Sulfo group, an OXo, stituted” and “lower alkynyl group optionally substituted for a halogen, anaromatic hydrocarbon group, a lower cycloalkyl X' include a lower alkyl group, a lower alkenyl group, a lower group, a lower cycloalkenyl group, a heterocyclic group, an alkynyl group, a lower alkoxy group, a lower alkanoyloxy acyl group, a lower alkylideneamino group, a lower alkylide group, a lower haloalkyl group (e.g., fluoromethyl, difluo neaminoxy group, a lower alkylidenehydrazino group, a romethyl, trifluoromethyl and the like), a lower haloalkyloxy lower alkylidenehydrazono group, group (e.g., fluoromethoxy, difluoromethoxy, trifluo (0343 a group represented by the formula: -SOX", romethoxy and the like), a hydroxyl group, a nitro group, a (0344) a group represented by the formula: —OX’, cyano group, a carboxyl group, a Sulfo group, an OXO, a (0345 a group represented by the formula: NCX), halogen, a lower cycloalkyl group, a lower cycloalkenyl (0346) a group represented by the formula: —ONCX), group, an aromatic hydrocarbon group optionally Substituted, (0347 a group represented by the formula: =NX’, a heterocyclic group optionally Substituted, an acyl group, a (0348 a group represented by the formula: =NOX’, lower alkylideneamino group, a lower alkylideneaminoxy (0349 a group represented by the formula: NCX)N group, a lower alkylidenehydrazino group, a lower alky (X2), lidenehydrazono group, 0350 a group represented by the formula: =NNCX'), 0323) a group represented by the formula: -SO,X', 10351) a group represented by the formula: C(=Q')N 0324 a group represented by the formula: —OX', (X )2. 0325 a group represented by the formula: NCX'), 0352 a group represented by the formula: C(=Q')N 0326) a group represented by the formula: —ONCX'), (X)N(X'), and the like. In this case, the number of the 0327 a group represented by the formula: =NX', substituent is preferably 1 to 3. 0328 a group represented by the formula: =NOX'. 0353. In the above-mentioned formulae, U represents an 0329 a group represented by the formula: NCX')N integer of 0, 1 or 2, (XI), 10354) X' represents a hydrogen atom, a lower alkyl 0330 a group represented by the formula: =NNCX'), group, a lower cycloalkyl group, a lower alkenyl group, a 19331) a group represented by the formula: —C(=Q')N lower cycloalkenyl group, a lower alkynyl group, an aromatic (X )2. hydrocarbon group optionally Substituted or a heterocyclic 0332 a group represented by the formula: —C(=Q')N group optionally substituted, and X’, X, XP, X, X’, (X')N(X'), and the like, X, X', X’, X, X’ and X’ represent each indepen 0333 and the number of the substituent is in a substitut dently a hydrogen atom, a lower alkyl group, a lower able range and 1 to 5, preferably 1 to 3. cycloalkyl group, a lower alkenyl group, a lower cycloalkenyl 0334. In the above-mentioned formulae, T represents an group, a lower alkynyl group, an aromatic hydrocarbon integer of 0, 1 or 2, group, a heterocyclic group, an acyl group, a group repre 0335 X' represents a hydrogen atom, a lower alkyl sented by the formula: -SOX, or group, a lower cycloalkyl group, a lower alkenyl group, a 0355 a group represented by the formula: C(=Q)N lower cycloalkenyl group, a lower alkynyl group, an aromatic (X29). hydrocarbon group or a heterocyclic group, 0356. Here, X and X’ represent each independently a 0336 XIP, X1C, XIP, XIE, XIF, X1G, XI H, XII, X1, XIK lower alkyl group, a lower cycloalkyl group, a lower alkenyl and X' represent each independently a hydrogen atom, a group, a lower cycloalkenyl group, a lower alkynyl group, an lower alkyl group, a lower cycloalkyl group, a lower alkenyl aromatic hydrocarbon group or a heterocyclic group. group, a lower cycloalkenyl group, a lower alkynyl group, an 0357 Q, Q’ and Q’ represent each independently an aromatic hydrocarbon group, heterocyclic group, an acyl oxygen atom or a Sulfur atom. grOup, 0358. When the “substituent” in the terms “lower alkyl 0337 a group represented by the formula: = SOX', or group optionally Substituted”. “lower cycloalkyl group 0338 a group represented by the formula: C(=Q')N optionally substituted”, “lower alkenyl group optionally sub (X'9). stituted”, “lower cycloalkenyl group optionally substituted US 2011/0319437 A1 Dec. 29, 2011 22 and “lower alkynyl group optionally substituted represents drazino group or alkylidenehydrazono group, or when one or an aromatic hydrocarbon group, a lower cycloalkyl group, a more of X34, X3/, X3C, X3D, x3F, x3F, X3G, X3H, X3, X3, lower cycloalkenyl group or a heterocyclic group, X, X, X and X’ are a lower alkyl group, a lower 0359 or, when one or more of X', X, X, XP, X', cycloalkyl group, a lower alkenyl group, a lower cycloalkenyl X1, X1,X17,X1, X1,X & XII, XI and X 9 represent an group or a lower alkynyl group, aromatic hydrocarbon group, a lower cycloalkyl group, a 0381 these groups maybe further substituted with a nitro lower cycloalkenyl group or a heterocyclic group, group, a cyano group, a carboxyl group, a Sulfo group, an OXo, 0360 these groups may be further substituted with a lower a halogen, anaromatic hydrocarbon group, a lower cycloalkyl alkyl group, a lower alkoxy group, a lower haloalkyl group group, a lower cycloalkenyl group, a heterocyclic group, an (e.g., fluoromethyl, difluoromethyl, trifluoromethyl and the acyl group, a lower alkylideneamino group, a lower alkylide like), a nitro group, a cyano group, a carboxyl group, a Sulfo neaminoxy group, a lower alkylidenehydrazino group, a group, a halogen, a lower cycloalkyl group, a lower alkenyl lower alkylidenehydrazono group, group, a lower cycloalkenyl group, a lower alkynyl group, an 0382 a group represented by the formula: SOX', aromatic hydrocarbon optionally Substituted, a heterocyclic 0383 a group represented by the formula: = OX', group optionally Substituted, an acyl group, a lower alkylide (0384 a group represented by the formula: NCX), neamino group, a lower alkylideneaminoxy group, a lower 0385) a group represented by the formula: = ONCXP), alkylidenehydrazino group, a lower alkylidenehydrazono 0386 a group represented by the formula: =NX', grOup, (0387 a group represented by the formula: =NOX', 0361) a group represented by the formula: -SOX', 0388 a group represented by the formula: NCX)N 0362) a group represented by the formula: —OX, (X4H. 2s 0363 a group represented by the formula: NCX), 0389 a group represented by the formula: =NNCX), 0364 a group represented by the formula: —ONCX), 0390 a group represented by the formula: C(=Q')N 0365 a group represented by the formula: =NX, (X), or 0366 a group represented by the formula: =NOX. 0391 a group represented by the formula: C(=Q')N 0367 a group represented by the formula: NCX)N (X^)N(x). (X3H 2s 0392. In this case, the number of the substituent is prefer 0368 a group represented by the formula: =NNCX), ably 1 to 3. 0369 a group represented by the formula: –C(—Q')N 0393. In the above-mentioned formulae, W represents an (X) or integer of 0, 1 or 2, 0370 a group represented by the formula: –C(—Q)N 0394 X' represents a hydrogen atom, a lower alkyl (X^)N(x). group, a lower cycloalkyl group, a lower alkenyl group, a 0371. In this case, the number of the substituent is prefer lower cycloalkenyl group, a lower alkynyl group, an aromatic ably 1 to 3. hydrocarbon group or a heterocyclic group, and X', X'. 0372. In the above-mentioned formulae, V represents an X-D, X-E, X-F, X4G, X4H. X1, X1, X1K and X4. represent integer of 0, 1 or 2, each independently a hydrogen atom, a lower alkyl group, a 0373 X represents a hydrogen atom, a lower alkyl lower cycloalkyl group, a lower alkenyl group, a lower group, a lower cycloalkyl group, a lower alkenyl group, a cycloalkenyl group, a lower alkynyl group, an aromatic lower cycloalkenyl group, a lower alkynyl group, an aromatic hydrocarbon group, a heterocyclic group, an acyl group, hydrocarbon group or a heterocyclic group, 0395 a group represented by the formula: -SOX', or 0374 X3/, X3C, X3D, X3,E, x3F, X3G, X3.H. X3, X3, X3 K 0396 a group represented by the formula: –C(=Q')N and X represent each independently a hydrogen atom, a (X9). lower alkyl group, a lower cycloalkyl group, a lower alkenyl 0397 Here, X and X' represent each independently a group, a lower cycloalkenyl group, a lower alkynyl group, an lower alkyl group, a lower cycloalkyl group, a C- alkenyl aromatic hydrocarbon group, a heterocyclic group, an acyl group, a lower cycloalkenyl group, a lower alkynyl group, an grOup, aromatic hydrocarbon group or a heterocyclic group, 0375 a group represented by the formula: -SOX, or 0398 Q, Q and Q represent each independently an 0376 a group represented by the formula: = C(=Q)N oxygen atom or a Sulfur atom. (X9). 0399 Suitable examples of substituents in the term “aro 0377 Here, X and X represent each independently a matic hydrocarbon group optionally substituted” for X' lower alkyl group, a lower cycloalkyl group, a lower alkenyl include a lower alkyl group, a lower alkenyl group, a lower group, a lower cycloalkenyl group, a lower alkynyl group, an alkynyl group, a lower alkoxy group, a lower alkanoyloxy aromatic hydrocarbon group or a heterocyclic group. group, a lower haloalkyl group (e.g., fluoromethyl, difluo 0378 Q', Q and Q represent each independently an romethyl, trifluoromethyl and the like), a lower haloalkyloxy oxygen atom or Sulfur atom. group (e.g., fluoromethoxy, difluoromethoxy, trifluo 0379 Further, the aromatic hydrocarbon group, lower romethoxy and the like), a hydroxyl group, a nitro group, a cycloalkyl group, lower cycloalkenyl group or heterocyclic cyano group, a carboxyl group, a Sulfo group, a halogen, a group has at least one substituent, or when one or more of lower cycloalkyl group, a lower cycloalkenyl group, an aro X11, XL5, XI c. XID, XIF, XIF, XI G. XIH, XII, XIV, Xik, XII, matic hydrocarbon group optionally Substituted, a heterocy X' and X’ are an aromatic hydrocarbon group, a lower clic group optionally Substituted, an acyl group, a lower alky cycloalkyl group or a lower cycloalkenyl group, the 3 to lideneamino group, a lower alkylideneaminoxy group, a 8-membered heterocyclic group has at least one Substituent, lower alkylidenehydrazino group, a lower alkylidenehydra and ZOno group, 0380 when these substituents are an acyl group, alkylide (0400 a group represented by the formula: SOX, neamino group, alkylideneaminoxy group, alkylidenehy (0401) a group represented by the formula: —OX, US 2011/0319437 A1 Dec. 29, 2011 23

(0402 a group represented by the formula: NCX), 0431. In the above-mentioned formulae, L represents an 0403 a group represented by the formula: —ONCXP), integer of 0, 1 or 2, (0404 a group represented by the formula: =NX, 0432 X' represents a hydrogen atom, a lower alkyl 04.05 a group represented by the formula: =NOX. group, a lower cycloalkyl group, a lower alkenyl group, a 04.06 a group represented by the formula: NCX)N lower cycloalkenyl group, a lower alkynyl group, an aromatic (xSH 2s hydrocarbon group or a heterocyclic group, (0407 a group represented by the formula: =NNCX), 0433 and X65, X6C, X6D, X6E, X6F, X6G, X6H, X61, X6. 0408 a group represented by the formula: —C(=Q)N X' and X' represent each independently a hydrogenatom, (X5’ 2s a lower alkyl group, a lower cycloalkyl group, a lower alkenyl 04.09 a group represented by the formula: –C(=O.)N group, a lower cycloalkenyl group, a lower alkynyl group, an (X*)N(X), and the like, aromatic hydrocarbon group, a heterocyclic group, an acyl 0410 and the number of the substituent is preferably 1 to grOup, 5, more preferably 1 to 3. 0434 a group represented by the formula: -SO-X", or 0411. In the above-mentioned formulae, K represents an 0435 a group represented by the formula: —C(=Q')N integer of 0, 1 or 2, (X9). 0412 X represents a hydrogen atom, a lower alkyl 0436. Here, X and X represent each independently a group, a lower cycloalkyl group, a lower alkenyl group, a lower alkyl group, a lower cycloalkyl group, a lower alkenyl lower cycloalkenyl group, a lower alkynyl group, an aromatic group, a lower cycloalkenyl group, a lower alkynyl group, an hydrocarbon group or a heterocyclic group, aromatic hydrocarbon group or a heterocyclic group, 0413 X51, X5C, X5P, X5E, X5F, X5G, X5H, X5, X5, X5K 0437 and Q, Q and Q represent each independently and X represent each independently a hydrogen atom, a an oxygen atom or a Sulfur atom. lower alkyl group, a lower cycloalkyl group, a lower alkenyl 0438. When the substituent in the “aromatic hydrocarbon group, a lower cycloalkenyl group, a lower alkynyl group, an group optionally Substituted” is an aromatic hydrocarbon aromatic hydrocarbon group, a heterocyclic group, acyl group, a lower cycloalkyl group, a lower cycloalkenyl group grOup, or a heterocyclic group, or when one or more of X, X’, 0414 a group represented by the formula: -SO.X, or X5C, X5P, X5E, X5F, X5G, X5H, X5, X5, X5K, X5L, X and 0415 a group represented by the formula: = C(=Q)N X are an aromatic hydrocarbon group, a lower cycloalkyl (X59). group or a heterocyclic group, 0416) Here, X and X represent each independently a 0439 these groups may be further substituted with 1 to 3 lower alkyl group, a lower cycloalkyl group, a lower alkenyl Substituents selected from the group consisting of a nitro group, a lower cycloalkenyl group, a lower alkynyl group, an group, a cyano group, a carboxyl group, a Sulfo group, a aromatic hydrocarbon group or a heterocyclic group, halogen, a lower alkyl group, a lower cycloalkyl group, a lower alkenyl group, a lower cycloalkenyl group, a lower 0417 and Q, Q and Q represent each independently alkynyl group, anaromatic hydrocarbon group, a heterocyclic an oxygen atom or Sulfur atom. group, an acyl group, a lower alkylideneamino group, a lower 0418 When the substituent in the “aromatic hydrocarbon alkylideneaminoxy group, a lower alkylidenehydrazino group optionally substituted” is an acyl group, alkylidene amino group, alkylideneaminoxy group, alkylidenehy group, a lower alkylidenehydrazono group, drazino group or alkylidenehydrazono group, 0440 a group represented by the formula: SOX', 0419 or, when one or more of X', X, X, XP, X, 0441) a group represented by the formula: —OX'. XS, XS, XS, XS, XS, XSS, XS, X5 and X59 are a lower 10442 a group represented by the formula: NCX"), alkyl group, a lower cycloalkyl group, a lower alkenyl group, 10443) a group represented by the formula: —ONCX'), a lower cycloalkenyl group or a lower alkynyl group, 0444 a group represented by the formula: =NX'. 0420 these groups may be further substituted with 1 to 3 0445 a group represented by the formula: =NOX'. Substituents selected from the group consisting of a nitro 0446 a group represented by the formula: NCX)N group, a cyano group, a carboxyl group, a Sulfo group, an OXo, (X7F 2s a halogen, an aromatic hydrocarbon group, a heterocyclic 0447 a group represented by the formula: =NNCX'), group, an acyl group, a lower alkylideneamino group, a lower alkylideneaminoxy group, a lower alkylidenehydrazino 0448 a group represented by the formula: C(=Q')N (X7 2s group, a lower alkylidenehydrazono group, 10449 a group represented by the formula: C(=Q')N 0421 a group represented by the formula: SOX', (X')N(X'), and the like. 0422 a group represented by the formula: —OX', 0450. In the above-mentioned formulae, M represents an 0423 a group represented by the formula: NCX"), integer of 0, 1 or 2, 0424 a group represented by the formula: —ONCX"), 0451 X' represents a hydrogen atom, a lower alkyl 0425 a group represented by the formula: =NX, group, a lower cycloalkyl group, a lower alkenyl group, a 0426 a group represented by the formula: =NOX. lower cycloalkenyl group, a lower alkynyl group, an aromatic 0427 a group represented by the formula: NCX)N hydrocarbon group or a heterocyclic group, (Xol), 0452 X75, X7c, X7P. X7F, X7F, X7G, X7H, X7. X7. X7K 0428 a group represented by the formula: =NNCX), and X' represent each independently a hydrogen atom, a 10429 a group represented by the formula: —C(=Q')N lower alkyl group, a lower cycloalkyl group, a lower alkenyl (X), group, a lower cycloalkenyl group, a C2-alkynyl group, an 0430 a group represented by the formula: —C(=Q')N aromatic hydrocarbon group, a heterocyclic group, acyl (X)N(X), and the like. grOup, US 2011/0319437 A1 Dec. 29, 2011 24

0453 a group represented by the formula: -SO.X', or 0469 For the substituent in the terms “lower alkyl group 0454 a group represented by the formula: = C(=Q7)N optionally substituted”, “lower cycloalkyl group optionally (X79). substituted”, “lower alkenyl group optionally substituted’, 0455. Here, X7 and X7 represent each independently a “lower cycloalkenyl group optionally substituted”, “lower lower alkyl group, a lower cycloalkyl group, a lower alkenyl alkynyl group optionally Substituted', 'aromatic hydrocar group, a lower cycloalkenyl group, a lower alkynyl group, an bon group optionally substituted” and "heterocyclic group aromatic hydrocarbon group or a heterocyclic group, and optionally substituted” for X, the “substituent” for X' Q', Q' and Q" represent each independently an oxygen describe above can be referred to. atom or a Sulfur atom. 0470 ForX2, Q22,XP2,X2, X2, X2, X2, X2 andX&2 0456. As the substituent in the "heterocyclic group option for X, groups described later can be referred to. ally substituted” for X', the same substituents as exemplified 0471) X represents a hydrogenatom, a lower alkyl group for the substituent of the 'aromatic hydrocarbon group optionally Substituted, a higher alkyl group, a lower optionally substituted” are mentioned. cycloalkyl group optionally substituted, a lower alkenyl 0457 X represents a lower alkyl group optionally substi group optionally substituted, a higher alkenyl group, a lower tuted, a higher alkyl group, a lower cycloalkyl group option cycloalkenyl group optionally Substituted, a lower alkynyl ally substituted, a lower alkenyl group optionally Substituted, group optionally substituted, a higher alkynyl group, an aro a higher alkenyl group, a lower cycloalkenyl group optionally matic hydrocarbon group optionally Substituted, a heterocy Substituted, a lower alkynyl group optionally Substituted, a clic group optionally substituted, C(=Q')X", C(=O) higher alkynyl group, an aromatic hydrocarbon group option OX13, C(-Q2)NXD3XP3 O SOX, ally substituted, a heterocyclic group optionally Substituted, 0472 and preferably mentioned is a lower alkyl group C( Q?)X', C(=O)CX, C( Q22)NXD2xf2, SOX2, optionally Substituted, or an aromatic hydrocarbon group NX'X', N=C(X'), OX^* or a cyano group, optionally substituted, and particularly preferably mentioned 0458 and preferably mentioned is a lower alkyl group is a lower alkyl group or an aromatic hydrocarbon group. optionally Substituted, an aromatic hydrocarbon group 0473 For the above-mentioned “lower alkyl group' in the optionally substituted, or C(=Q')X' (here, Q’ represents term “lower alkyl group optionally substituted” for X, the an oxygen atom, and X" represents a lower alkyl group “lower alkyl group' described above can be referred to. optionally Substituted), and particularly preferably men 0474 For the above-mentioned “higher alkyl group' for tioned is a lower alkyl group Substituted with at least one X, the “higher alkyl group” described above can be referred aromatic hydrocarbon group, an aromatic hydrocarbon group tO. or a lower alkanoyl group. 0475 For the above-mentioned “lower cycloalkyl group' 0459 For the above-mentioned “lower alkyl group' in the in the term “lower cycloalkyl group optionally substituted term “lower alkyl group optionally substituted” for X, the for X, the “lower cycloalkyl group' described above can be “lower alkyl group' described above can be referred to. referred to. 0460 For the above-mentioned “higher alkyl group' for 0476 For the above-mentioned “lower alkenyl group' in X, the “higher alkyl group' described above can be referred the term “lower alkenyl group optionally substituted for X, tO. the “lower alkenyl group' described above can be referred to. 0461 For the above-mentioned “lower cycloalkyl group' 0477 For the above-mentioned “lower cycloalkenyl in the term “lower cycloalkyl group optionally substituted group' in the term “lower cycloalkenyl group optionally Sub for X, the “lower cycloalkyl group” described above can be stituted” for X, the “lower cycloalkenyl group” described referred to. above can be referred to. 0462 For the above-mentioned “lower alkenyl group' in 0478 For the above-mentioned “lower alkynyl group' in the term “lower alkenyl group optionally substituted” for X, the term “lower alkynyl group optionally substituted” for X, the “lower alkenyl group' described above can be referred to. the “lower alkynyl group' described above can be referred to. 0463 For the above-mentioned “higher alkenyl group' for 0479. For the above-mentioned “higher alkynyl group' for X, the “higher alkenyl group” described above can be X, the “higher alkynyl group” described above can be referred to. referred to. 0464 For the above-mentioned “lower cycloalkenyl 0480. For the above-mentioned “aromatic hydrocarbon group' in the term “lower cycloalkenyl group optionally Sub group' in the term 'aromatic hydrocarbon group optionally stituted” for X, the “lower cycloalkenyl group” described substituted” for X, the “aromatic hydrocarbon group” above can be referred to. described above can be referred to. 0465 For the above-mentioned “lower alkynyl group' in 0481 For the above-mentioned "heterocyclic group” in the term “lower alkynyl group optionally substituted” for X, the term "heterocyclic group optionally substituted, the the “lower alkynyl group' described above can be referred to. "heterocyclic group' described above can be referred to. 0466 For the above-mentioned “higher alkynyl group' for 0482 For the substituent in the terms “lower alkyl group X, the "higher alkynyl group” described above can be optionally substituted”, “lower cycloalkyl group optionally referred to. substituted”, “lower alkenyl group optionally substituted’, 0467 For the above-mentioned “aromatic hydrocarbon “lower cycloalkenyl group optionally substituted”, “lower group' in the term 'aromatic hydrocarbon group optionally alkynyl group optionally Substituted', 'aromatic hydrocar substituted” for X, the 'aromatic hydrocarbon group” bon group optionally substituted” and "heterocyclic group described above can be referred to. optionally substituted” for X, the “substituent” for X' 0468 For the above-mentioned "heterocyclic group” in describe above can be referred to. the term "heterocyclic group optionally substituted” for X, 0483 ForX, X', Q, XP, X- and X forX, groups the "heterocyclic group' described above can be referred to. described later can be referred to. US 2011/0319437 A1 Dec. 29, 2011

0484. For the “ring structure” represented by X and X 0497 For the substituent in the above-mentioned term together with the nitrogen which is bonded with each other, “aromatic hydrocarbon group optionally substituted” for X, the same structures as the below-mentioned “ring structure' the “substituent” for X' described above can be referred to, represented by XP and X, XP and X2, XP and X, XP and preferably mentioned is a halogen, a nitro group, a lower and X*, YP and YE1, YP2 and Y-2, Yip and YE, YP and alkyl group, a lower haloalkyl group or a lower alkoxy group. Y', and ZP and Z together with the nitrogen which is 0498 For the above-mentioned "heterocyclic group” in bonded with each other are mentioned. the term "heterocyclic group optionally substituted” for X, 0485 X represents a lower alkyl group optionally substi the "heterocyclic group' described above can be referred to. tuted, a higher alkyl group, a lower cycloalkyl group option 0499 For the substituent in the above-mentioned term ally substituted, a lower alkenyl group optionally Substituted, "heterocyclic group optionally substituted” for X, the “sub a lower cycloalkenyl group optionally substituted, a higher stituent” for X' described above can be referred to, and pref alkenyl group, a lower alkynyl group optionally Substituted, a erably mentioned is a lower alkyl group. higher alkynyl group, an aromatic hydrocarbon group option (0500 For the substituent in the terms “lower cycloalkyl ally substituted, a heterocyclic group optionally Substituted, group optionally Substituted”. “lower alkenyl group option C( Q')X', C(O)OX, C( Q')NXX* or S(O) ally substituted”, “lower cycloalkenyl group optionally sub X4, stituted and “lower alkynyl group optionally substituted for 0486 and preferably mentioned is a lower alkyl group X, the “substituent” for X' described above can be referred optionally substituted, a higher alkyl group, a lower alkenyl tO. group optionally Substituted, a lower cycloalkyl group 0501. For Qi, X1, X*, Qi, X, X- and X* for X, optionally Substituted, an aromatic hydrocarbon group groups described later can be referred to. optionally substituted or a heterocyclic group optionally Sub (0502 X represents a lower alkyl group optionally substi stituted, and particularly preferably mentioned is a lower tuted, a higher alkyl group, a lower cycloalkyl group option alkyl group optionally Substituted, a higher alkyl group, a ally substituted, a lower alkenyl group optionally Substituted, lower cycloalkyl group, a lower alkenyl group, an aromatic a higher alkenyl group, a lower cycloalkenyl group optionally hydrocarbon group optionally substituted or a heterocyclic Substituted, a lower alkynyl group optionally Substituted, a group optionally Substituted. higher alkynyl group, an aromatic hydrocarbon group option 0487. For the above-mentioned “lower alkyl group' in the ally substituted or a heterocyclic group optionally Substituted term “lower alkyl group optionally substituted” for X, the 0503 and preferably mentioned is an aromatic hydrocar “lower alkyl group' described above can be referred to. bon group optionally substituted, and particularly mentioned 0488 For the substituent in the term “lower alkyl group optionally substituted” for X, the “substituent” for X' is an aromatic hydrocarbon group. described above can be referred to, and preferably mentioned 0504 For the above-mentioned “lower alkyl group' in the is an aromatic hydrocarbon group optionally substituted or a term “lower alkyl group optionally substituted” for X, the heterocyclic group optionally Substituted, and particularly “lower alkyl group' described above can be referred to. preferably mentioned is an aromatic hydrocarbon optionally 0505 For the above-mentioned “higher alkyl group' for Substituted with at least one halogen or a heterocyclic group X, the “higher alkyl group' described above can be referred Substituted with at least one halogen. tO. 0489 For the above-mentioned “higher alkyl group' for 0506 For the above-mentioned “lower cycloalkyl group' X, the “higher alkyl group” described above can be referred in the term “lower cycloalkyl group optionally substituted tO. for X, the “lower cycloalkyl group” described above can be 0490 For the above-mentioned “lower cycloalkyl group' referred to. in the term “lower cycloalkyl group optionally substituted 0507 For the above-mentioned “lower alkenyl group' in for X, the “lower cycloalkyl group' described above can be the term “lower alkenyl group optionally substituted” for X, referred to. the “lower alkenyl group' described above can be referred to. 0491 For the above-mentioned “lower alkenyl group' in 0508 For the above-mentioned “higher alkenyl group' for the term “lower alkenyl group optionally substituted” for X, X, the “higher alkenyl group” described above can be the “lower alkenyl group' described above can be referred to. referred to. 0492 For the above-mentioned “higher alkenyl group' for (0509 For the above-mentioned “lower cycloalkenyl X, the “higher alkenyl group” described above can be group' in the term “lower cycloalkenyl group optionally Sub referred to. stituted” for X, the “lower cycloalkenyl group” described 0493 For the above-mentioned “lower cycloalkenyl above can be referred to. group' in the term “lower cycloalkenyl group optionally Sub 0510 For the above-mentioned “lower alkynyl group' in stituted” for X, the “lower cycloalkenyl group' described the term “lower alkynyl group optionally substituted” for X, above can be referred to. the “lower alkynyl group' described above can be referred to. 0494 For the above-mentioned “lower alkynyl group' in 0511 For the above-mentioned “higher alkynyl group' for the term “lower alkynyl group optionally substituted” for X, X, the “higher alkynyl group” described above can be the “lower alkynyl group' described above can be referred to. referred to. 0495 For the above-mentioned “higher alkynyl group' for 0512 For the above-mentioned “aromatic hydrocarbon X, the "higher alkynyl group” described above can be group' in the term 'aromatic hydrocarbon group optionally referred to. substituted for X, the 'aromatic hydrocarbon group” 0496 For the above-mentioned “aromatic hydrocarbon described above can be referred to. group' in the term 'aromatic hydrocarbon group optionally 0513 For the above-mentioned "heterocyclic group” in substituted” for X, the 'aromatic hydrocarbon group” the term "heterocyclic group optionally substituted” for X, described above can be referred to. the "heterocyclic group' described above can be referred to. US 2011/0319437 A1 Dec. 29, 2011 26

0514 For the substituent in the terms “lower alkyl group group, a lower cycloalkyl group optionally Substituted, a optionally substituted”, “lower cycloalkyl group optionally lower alkenyl group optionally Substituted, a higher alkenyl substituted”, “lower alkenyl group optionally substituted’, group, a lower cycloalkenyl group optionally substituted, a “lower cycloalkenyl group optionally substituted”, “lower lower alkynyl group optionally Substituted, a higher alkynyl alkynyl group optionally substituted', 'aromatic hydrocar group, an aromatic hydrocarbon group optionally Substituted, bon group optionally substituted” and "heterocyclic group a heterocyclic group optionally substituted, OX-7, SX' or optionally substituted” for X, the “substituent” for X' NXG7XH7, described above can be referred to. 0529 alternatively, represent a reig structure together with 0515 X's represent each independently a lower alkyl the carbon atom which is bonded with each other. group optionally substituted, a higher alkyl group, a lower 0530 For the above-mentioned “lower alkyl group' in the cycloalkyl group optionally substituted, a lower alkenyl term “lower alkyl group optionally substituted” for X7, the group optionally substituted, a higher alkenyl group, a lower “lower alkyl group' described above can be referred to. cycloalkenyl group optionally Substituted, a lower alkynyl 0531. For the above-mentioned “higher alkyl group' for group optionally substituted, a higher alkynyl group, an aro X", the “higher alkyl group” described above can be referred matic hydrocarbon group optionally Substituted, a heterocy tO. clic group optionally Substituted or a lower alkoxy group 0532. For the above-mentioned “lower cycloalkyl group' optionally substituted. in the term “lower cycloalkyl group optionally substituted 0516 For the above-mentioned “lower alkyl group' in the for X7, the “lower cycloalkyl group' described above can be term “lower alkyl group optionally substituted” for X, the referred to. “lower alkyl group' described above can be referred to. 0533. For the above-mentioned “lower alkenyl group' in 0517 For the above-mentioned “higher alkyl group' for the term “lower alkenyl group optionally substituted for X7. X, the “higher alkyl group” described above can be referred the “lower alkenyl group' described above can be referred to. tO. 0534 For the above-mentioned “higher alkenyl group' for 0518. For the above-mentioned “lower cycloalkyl group' X", the “higher alkenyl group” described above can be in the term “lower cycloalkyl group optionally substituted referred to. for X, the “lower cycloalkyl group' described above can be 0535. For the above-mentioned “lower cycloalkenyl referred to. group' in the term “lower cycloalkenyl group optionally Sub 0519 For the above-mentioned “lower alkenyl group' in stituted for X7, the “lower cycloalkenyl group' described the term “lower alkenyl group optionally substituted” for X, above can be referred to. the “lower alkenyl group' described above can be referred to. 0536 For the above-mentioned “lower alkynyl group' in 0520 For the above-mentioned “higher alkenyl group' for the term “lower alkynyl group optionally substituted for X7. X, the “higher alkenyl group” described above can be the “lower alkynyl group' described above can be referred to. referred to. 0537 For the above-mentioned “higher alkynyl group' for 0521 For the above-mentioned “lower cycloalkenyl X", the “higher alkynyl group” described above can be group' in the term “lower cycloalkenyl group optionally Sub referred to. stituted” for X, the “lower cycloalkenyl group' described 0538 For the above-mentioned “aromatic hydrocarbon above can be referred to. group' in the term 'aromatic hydrocarbon group optionally 0522 For the above-mentioned “lower alkynyl group' in substituted for X7, the 'aromatic hydrocarbon group” the term “lower alkynyl group optionally substituted” for X, described above can be referred to. the “lower alkynyl group' described above can be referred to. 0539 For the above-mentioned "heterocyclic group” in 0523 For the above-mentioned “higher alkynyl group' for the term "heterocyclic group optionally substituted” for X7. X, the "higher alkynyl group” described above can be the "heterocyclic group' described above can be referred to. referred to. 0540 For the substituent in the terms “lower alkyl group 0524 For the above-mentioned “aromatic hydrocarbon optionally substituted”, “lower cycloalkyl group optionally group' in the term 'aromatic hydrocarbon group optionally substituted”, “lower alkenyl group optionally substituted’, substituted” for X, the “aromatic hydrocarbon group” “lower cycloalkenyl group optionally substituted”, “lower described above can be referred to. alkynyl group optionally Substituted', 'aromatic hydrocar 0525 For the above-mentioned "heterocyclic group” in bon group optionally substituted” and "heterocyclic group the term "heterocyclic group optionally substituted” for X, optionally substituted” for X7, the “substituent” for X' the "heterocyclic group' described above can be referred to. described above can be referred to. 0526 For the above-mentioned “lower alkoxy group' in 0541. For the "heterocyclic group' in the term "heterocy the term “lower alkoxy group optionally substituted” for X clic group optionally substituted for X, the "heterocyclic the “lower alkoxy group' described above can be referred to. group' described above can be referred to, and preferably 0527. For the substituent in the terms “lower alkyl group mentioned is a heterocyclic group, particularly preferably optionally substituted”, “lower cycloalkyl group optionally mentioned is a piperidino group or morpholino group. substituted”, “lower alkenyl group optionally substituted’, (0542. For X7, X7, X7 and X7, groups described “lower cycloalkenyl group optionally substituted”, “lower below can be referred to. alkynyl group optionally substituted', 'aromatic hydrocar (0543. The “ring structure” represented by X's together bon group optionally substituted, "heterocyclic group with the carbon which is bonded with each other means a 3 to optionally substituted and “lower alkoxy group optionally 8-membered cyclic group composed of the carbon atom as a substituted” for X, the “substituent” for X' described above ring constituent atom, and mentioned are 3 to 8-membered can be referred to. (preferably, 5 to 6-membered) cyclic groups composed of the 0528 X's represent each independently a hydrogenatom, carbonatom as a ring constituent atom, and optionally having a lower alkyl group optionally Substituted, a higher alkyl 1 to 3 hetero atoms such as a nitrogen atom optionally oxi US 2011/0319437 A1 Dec. 29, 2011 27 dized, an oxygen atom, a Sulfur atom optionally mono or 0552 For the above-mentioned “higher alkyl group' forY. di-oxidized, and the like Such as, for example, cyclopentyl the “higher alkyl group' described above can be referred to. idene, cyclohexylidene, cycloheptylidene, cyclooctylidene, 0553 For the above-mentioned “lower cycloalkyl group' cyclopentenylidene, cyclohexenylidene, cycloheptenylidene, in the term “lower cycloalkyl group optionally substituted cyclooctenylidene, cyclopentadienylidene, cyclohexadi for Y', the “lower cycloalkyl group” described above can be enylidene, cycloheptadienylidene, cyclooctadienylidene, tet referred to. rahydrofuranylidene, dihydrofuranylidene, tetrahydropyra 0554 For the above-mentioned “lower alkenyl group' in nylidene, dihydropyranylidene, pyranylidene, the term “lower alkenyl group optionally substituted” forY', dioxolanylidene, dioxolylidene, dioxanylidene, dioxi the “lower alkenyl group' described above can be referred to. nylidene, tetrahydrothiophenylidene, dihydrothiophe 0555 For the above-mentioned “higher alkenyl group' for nylidene, tetrahydrothiopyranylidene, dihydrothiopyra Y', the “higher alkenyl group” described above can be nylidene, thiopyranylidene, dithiolanylidene, dithiolylidene, referred to. dithianylidene, dithiinylidene, 2H-dihydropyrrolylidene, 0556. For the above-mentioned “lower cycloalkenyl 2H-pyrrolylidene, 3H-pyrrolylidene, 2H-imidazolylidene, group' in the term “lower cycloalkenyl group optionally Sub 3H-triazolylidene and the like; and groups obtained by con stituted” for Y', the “lower cycloalkenyl group” described densing a benzene ring or 3 to 8-membered (preferably, 5 to above can be referred to. 6-membered) heterocyclic group (the heterocyclic group has 0557. For the above-mentioned “lower alkynyl group' in 1 to 4 nitrogen atom(s) optionally oxidized, oxygen atom(s), the term “lower alkynyl group optionally substituted” forY', or sulfur atom(s) optionally mono or di-oxidized) with the the “lower alkynyl group' described above can be referred to. above-mentioned cyclic group. 0558 For the above-mentioned “higher alkynyl group' for 0544 The “3 to 8-membered cyclic group composed of Y', the “higher alkynyl group” described above can be the carbon atom as a ring constituent atom' may be substi referred to. tuted with the same substituent as exemplified for the sub 0559 For the above-mentioned “aromatic hydrocarbon stituent on 'aromatic hydrocarbon group optionally substi group' in the term 'aromatic hydrocarbon group optionally tuted” for X'. The number of the substituent is in a substituted” for Y', the “aromatic hydrocarbon group” substitutable range and 1 to 5, preferably 1 to 3. described above can be referred to. 0545 QX4, Q-42, Qx43, Qx44, Q-45, Qx46, Qx47, Qx48, 0560 For the substituent in the term “aromatic hydrocar Q7, Q, Q , Q, Q and Q representeachinde bon group optionally substituted” forY', the “substituent” for pendently an oxygen atom or a Sulfur atom. X' described above can be referred to, and preferably men 0546 RX4, RX42, RX13, RX44, RX45, RX46, RX47, RX4s, tioned are a halogen, a lower alkyl group, a cyano group and RX49, RX410, RX111, RX412, QV, QV2, QV3, Qxh4, Qvis, a nitro group. Q', Q7, Q and Q’ represent each independently a 0561 For the above-mentioned "heterocyclic group” in hydrogen atom, a lower alkyl group, a lower cycloalkyl the term "heterocyclic group optionally substituted” for Y', group, a lower alkenyl group, a lower cycloalkenyl group, a the "heterocyclic group' described above can be referred to. lower alkynyl group or an aromatic hydrocarbon group. 0562 For the substituent in the term "heterocyclic group optionally substituted” for Y', the “substituent” for X' (0547. In the compound (I), Y represents OY, NY'Y, described above can be referred to. SY, SOY or N=C(Y). 0563 For the substituent in the terms “lower cycloalkyl (0548 Y' represents a lower alkyl group optionally substi group optionally Substituted”. “lower alkenyl group option tuted, a higher alkyl group, a lower cycloalkyl group option ally substituted”, “lower cycloalkenyl group optionally sub ally substituted, a lower alkenyl group optionally Substituted, stituted and “lower alkynyl group optionally substituted for a higher alkenyl group, a lower cycloalkenyl group optionally Y', the “substituents” for X' described above can be referred Substituted, a lower alkynyl group optionally Substituted, a tO. higher alkynyl group, an aromatic hydrocarbon group option 0564 For Q', Y41, YBl, Q2, YD1, YE1, Y and Yi, ally substituted, a heterocyclic group optionally Substituted, groups described later can be referred to. C(—Q)X', C(O)OY, C(-Q52)NYPYE, S(O).Y. 0565 Y represents a lower alkyl group optionally substi O N(Y), tuted, a higher alkyl group, a lower cycloalkyl group option 0549 and preferably mentioned is a lower alkyl group ally substituted, a lower alkenyl group optionally Substituted, optionally Substituted, an aromatic hydrocarbon group a higher alkenyl group, a lower cycloalkenyl group optionally optionally substituted or a heterocyclic group optionally Sub Substituted, a lower alkynyl group optionally Substituted, a stituted, and particularly preferably mentioned is a lower higher alkynyl group, an aromatic hydrocarbon group option alkyl optionally Substituted, an aromatic hydrocarbon group ally substituted, a heterocyclic group optionally Substituted, optionally substituted or a heterocyclic group. C(-Q°)Y12, C(O)OY, C(-Q62)NYP2YE2, SO.Y.2, 0550 For the above-mentioned “lower alkyl group” in the NY'Y', N=C(Y'), OY^* or a cyano group, term “lower alkyl group optionally substituted for Y, the 0566 and preferably mentioned is a lower alkyl group “lower alkyl group' described above can be referred to. optionally Substituted, or an aromatic hydrocarbon group 0551 For the substituent in the term “lower alkyl group optionally substituted, and particularly mentioned is a lower optionally substituted” for Y', the “substituent” for X' alkyl group optionally Substituted or an aromatic hydrocar describe above can be referred to, and preferably mentioned is bon group. an aromatic hydrocarbon group optionally substituted or a 0567 For the above-mentioned “lower alkyl group' in the heterocyclic group optionally Substituted, and particularly term “lower alkyl group optionally substituted” for Y, the preferably mentioned is an aromatic hydrocarbon optionally “lower alkyl group' described above can be referred to. substituted with at least one lower alkyl or halogen or a 0568 For the substituent in the term “lower alkyl group heterocyclic group Substituted with at least one halogen. optionally substituted for Y', the “substituent” for X' US 2011/0319437 A1 Dec. 29, 2011 28 described above can be referred to, and preferably mentioned 0584 For the above-mentioned “lower alkenyl group' in is an aromatic hydrocarbon group. the term “lower alkenyl group optionally substituted” forY. 0569. For the above-mentioned “higher alkyl group' for the “lower alkenyl group' described above can be referred to. Y, the “higher alkyl group” described above can be referred 0585 For the above-mentioned “higher alkenyl group' for tO Y, the “higher alkenyl group” described above can be 0570 For the above-mentioned “lower cycloalkyl group' referred to. in the term “lower cycloalkyl group optionally substituted 0586 For the above-mentioned “lower cycloalkenyl for Y, the “lower cycloalkyl group” described above can be group' in the term “lower cycloalkenyl group optionally Sub referred to. stituted for Y, the “lower cycloalkenyl group' described 0571 For the above-mentioned “lower alkenyl group' in above can be referred to. the term “lower alkenyl group optionally substituted” forY. 0587. For the above-mentioned “lower alkynyl group' in the “lower alkenyl group' described above can be referred to. the term “lower alkynyl group optionally substituted” forY. 0572 For the above-mentioned “higher alkenyl group' for the “lower alkynyl group' described above can be referred to. Y, the “higher alkenyl group” described above can be 0588 For the above-mentioned “higher alkynyl group' for referred to. Y, the “higher alkynyl group” described above can be referred to. 0573 For the above-mentioned “lower cycloalkenyl 0589 For the above-mentioned “aromatic hydrocarbon group' in the term “lower cycloalkenyl group optionally Sub group' in the term 'aromatic hydrocarbon group optionally stituted” for Y, the “lower cycloalkenyl group” described substituted for Y, the “aromatic hydrocarbon group” above can be referred to. described above can be referred to. 0574 For the above-mentioned “lower alkynyl group' in 0590 For the above-mentioned "heterocyclic group” in the term “lower alkynyl group optionally substituted” forY. the term "heterocyclic group optionally substituted” for Y, the “lower alkynyl group' described above can be referred to. the "heterocyclic group' described above can be referred to. 0575 For the above-mentioned “higher alkynyl group' for 0591 For the substituent in the terms “lower alkyl group Y, the “higher alkynyl group” described above can be optionally substituted”, “lower cycloalkyl group optionally referred to. substituted”, “lower alkenyl group optionally substituted’, 0576 For the above-mentioned “aromatic hydrocarbon “lower cycloalkenyl group optionally substituted”, “lower group' in the term 'aromatic hydrocarbon group optionally alkynyl group optionally Substituted', 'aromatic hydrocar substituted” for Y, the “aromatic hydrocarbon group” bon group optionally substituted” and "heterocyclic group described above can be referred to. optionally substituted” for Y, the “substituents” for X' 0577. For the above-mentioned “heterocyclic group” in described above can be referred to. the term "heterocyclic group optionally substituted” for Y, 0592 For Q7, Y43, Yiis, Q72, YP3, YE3 and YF3, groups the "heterocyclic group' described above can be referred to. described later can be referred to. 0578. For the substituent in the terms “lower cycloalkyl 0593. Y' represents a lower alkyl group optionally substi group optionally Substituted”. “lower alkenyl group option tuted, a higher alkyl group, a lower cycloalkyl group option ally substituted”, “lower cycloalkenyl group optionally sub ally substituted, a lower alkenyl group optionally Substituted, stituted”, “lower alkynyl group optionally substituted”, “aro a higher alkenyl group, a lower cycloalkenyl group optionally matic hydrocarbon group optionally Substituted” and Substituted, a lower alkynyl group optionally Substituted, a "heterocyclic group optionally substituted for Y, the “sub higher alkynyl group, an aromatic hydrocarbon group option stituents” for X' described above can be referred to. ally substituted, a heterocyclic group optionally Substituted, C(-QI)Y-1, C(—O)OY7, C(-Q82)NY Y- or S(O) 0579 For Q', Y42,YP2, Q92, YD2, YE2, YF2, YG2,YH2Y-2 YF4. and Y^f, groups described later can be referred to. fo594) and preferably mentioned is a lower alkyl group 0580 Y represents a hydrogenatom, a lower alkyl group optionally Substituted, a higher alkyl group, a lower optionally Substituted, a higher alkyl group, a lower cycloalkyl group optionally substituted, a lower alkenyl cycloalkyl group optionally substituted, a lower alkenyl group optionally Substituted, a higher alkenyl group, an aro group optionally substituted, a higher alkenyl group, a lower matic hydrocarbon group optionally Substituted or a hetero cycloalkenyl group optionally Substituted, a lower alkynyl cyclic group optionally Substituted, and particularly men group optionally substituted, a higher alkynyl group, an aro tioned is a lower alkyl group optionally substituted, a lower matic hydrocarbon group optionally Substituted, a heterocy cycloalkyl group optionally substituted, a lower alkenyl clic group optionally substituted, C(=Q7)Y', C(=O) group optionally Substituted, an aromatic hydrocarbon group OY, C(-Q')NYPY or SOY, and preferably optionally substituted or a heterocyclic group. mentioned is a lower alkyl group optionally Substituted, and 0595. For the above-mentioned “lower alkyl group” in the particularly mentioned is a lower alkyl group. term “lower alkyl group optionally substituted” for Y, the 0581 For the above-mentioned “lower alkyl group' in the “lower alkyl group' described above can be referred to. term “lower alkyl group optionally substituted” for Y, the 0596 For the substituent in the term “lower alkyl group “lower alkyl group' described above can be referred to. optionally substituted” for Y, the “substituents” for X' 0582 For the above-mentioned “higher alkyl group' for describe above can be referred to, and preferably mentioned is Y, the “higher alkyl group” described above can be referred an aromatic hydrocarbon group optionally Substituted, and tO particularly preferably mentioned is an aromatic hydrocarbon 0583. For the above-mentioned “lower cycloalkyl group' group Substituted with at least one halogen. in the term “lower cycloalkyl group optionally substituted 0597 For the above-mentioned “higher alkyl group” for for Y, the “lower cycloalkyl group' described above can be Y', the “higher alkyl group' described above can be referred referred to. tO. US 2011/0319437 A1 Dec. 29, 2011 29

0598. For the above-mentioned “lower cycloalkyl group' 0615. For the above-mentioned “lower cycloalkenyl in the term “lower cycloalkyl group optionally substituted group' in the term “lower cycloalkenyl group optionally Sub for Y, the “lower cycloalkyl group” described above can be stituted” for Y, the “lower cycloalkenyl group” described referred to. above can be referred to. 0599 For the above-mentioned “lower alkenyl group” in 0616) For the above-mentioned “lower alkynyl group' in the term “lower alkenyl group optionally substituted” forY. the term “lower alkynyl group optionally substituted” forY. the “lower alkenyl group' described above can be referred to. the “lower alkynyl group' described above can be referred to. 0600 For the above-mentioned “higher alkenyl group' for 0.617 For the above-mentioned “higher alkynyl group' for Y', the “higher alkenyl group” described above can be Y, the “higher alkynyl group” described above can be referred to. referred to. 0601 For the above-mentioned “lower cycloalkenyl 0618. For the above-mentioned “aromatic hydrocarbon group' in the term “lower cycloalkenyl group optionally Sub group' in the term 'aromatic hydrocarbon group optionally stituted” for Y, the “lower cycloalkenyl group” described substituted for Y, the “aromatic hydrocarbon group” above can be referred to. described above can be referred to. 0602 For the above-mentioned “lower alkynyl group' in 0619 For the above-mentioned "heterocyclic group” in the term “lower alkynyl group optionally substituted” forY. the term "heterocyclic group optionally substituted” for Y, the “lower alkynyl group' described above can be referred to. the "heterocyclic group' described above can be referred to. 0620. For the substituent in the terms “lower alkyl group 0603 For the above-mentioned “higher alkynyl group' for optionally substituted”, “lower cycloalkyl group optionally Y', the "higher alkynyl group” described above can be substituted”, “lower alkenyl group optionally substituted’, referred to. “lower cycloalkenyl group optionally substituted”, “lower 0604 For the above-mentioned “aromatic hydrocarbon alkynyl group optionally Substituted', 'aromatic hydrocar group' in the term 'aromatic hydrocarbon group optionally bon group optionally substituted” and "heterocyclic group substituted” for Y, the “aromatic hydrocarbon group” optionally substituted for Y, the “substituent” for X' described above can be referred to. described above can be referred to. 0605 For the substituent in the term “aromatic hydrocar 0621. Y's represent each independently a hydrogenatom, bon group optionally substituted” for Y, the “substituents” a lower alkyl group optionally Substituted, a higher alkyl for X" describe above can be referred to, and preferably men group, a lower cycloalkyl group optionally Substituted, a tioned area halogen, a lower haloalkyl group, a lower alkoxy lower alkenyl group optionally substituted, a higher alkenyl group and a lower haloalkyloxy group. group, a lower cycloalkenyl group optionally substituted, a 0606 For the above-mentioned "heterocyclic group” in lower alkynyl group optionally Substituted, a higher alkynyl the term "heterocyclic group optionally substituted” for Y, group, an aromatic hydrocarbon group optionally Substituted, the "heterocyclic group' described above can be referred to. a heterocyclic group optionally substituted, OY, SY' or 0607 For the substituent in the terms “lower cycloalkyl NYGGYH6, group optionally Substituted”. “lower alkenyl group option 0622 alternatively, representaring structure together with ally substituted”, “lower cycloalkenyl group optionally sub the carbon which is bonded with each other. stituted”, “lower alkynyl group optionally substituted and 0623 For the above-mentioned “lower alkyl group' in the "heterocyclic group optionally substituted” for Y', the “sub term “lower alkyl group optionally substituted” for Y, the stituents” for X" describe above can be referred to. “lower alkyl group' described above can be referred to. 0608 For Q, Y44, YB4. Q82, YP, Y-E4 and Y, groups 0624 For the above-mentioned “higher alkyl group' for described later can be referred to. Y', the “higher alkyl group” described above can be referred 0609 Y represents a lower alkyl group optionally substi tO. tuted, a higher alkyl group, a lower cycloalkyl group option 0625 For the above-mentioned “lower cycloalkyl group' ally substituted, a lower alkenyl group optionally Substituted, in the term “lower cycloalkyl group optionally substituted a higher alkenyl group, a lower cycloalkenyl group optionally for Y, the “lower cycloalkyl group' described above can be Substituted, a lower alkynyl group optionally Substituted, a referred to. higher alkynyl group, an aromatic hydrocarbon group option 0626. For the above-mentioned “lower alkenyl group' in ally Substituted or a heterocyclic group optionally Substituted. the term “lower alkenyl group optionally substituted” forY. 0610 For the above-mentioned “lower alkyl group' in the the “lower alkenyl group' described above can be referred to. term “lower alkyl group optionally substituted” for Y, the 0627. For the above-mentioned “higher alkenyl group' for “lower alkyl group' described above can be referred to. Y', the “higher alkenyl group” described above can be 0611 For the above-mentioned “higher alkyl group' for referred to. Y, the “higher alkyl group' described above can be referred 0628 For the above-mentioned “lower cycloalkenyl tO. group' in the term “lower cycloalkenyl group optionally Sub 0612 For the above-mentioned “lower cycloalkyl group' stituted for Y, the “lower cycloalkenyl group' described in the term “lower cycloalkyl group optionally substituted above can be referred to. for Y, the “lower cycloalkyl group' described above can be 0629. For the above-mentioned “lower alkynyl group' in referred to. the term “lower alkynyl group optionally substituted” forY. 0613 For the above-mentioned “lower alkenyl group' in the “lower alkynyl group' described above can be referred to. the term “lower alkenyl group optionally substituted for Y, 0630. For the above-mentioned “higher alkynyl group' for the “lower alkenyl group' described above can be referred to. Y', the “higher alkynyl group” described above can be 0614 For the above-mentioned “higher alkenyl group' for referred to. Y, the “higher alkenyl group” described above can be 0631 For the above-mentioned “aromatic hydrocarbon referred to. group' in the term 'aromatic hydrocarbon group optionally US 2011/0319437 A1 Dec. 29, 2011 30 substituted” for Y', the “aromatic hydrocarbon group” substituted for Z, the “aromatic hydrocarbon group' described above can be referred to. described above can be referred to. 0632 For the above-mentioned "heterocyclic group” in 0647. For the substituent in the term “aromatic hydrocar the term "heterocyclic group optionally substituted” for Y, bon group optionally substituted for Z, the “substituent for the "heterocyclic group' described above can be referred to. X' described above can be referred to, and preferably men 0633 For the substituent in the terms “lower alkyl group tioned is a halogen, a nitro group, a cyano group, a hydroxy optionally substituted”, “lower cycloalkyl group optionally group, a lower alkyl group, a lower haloalkyl group, a lower substituted”, “lower alkenyl group optionally substituted’, alkenyl group, a lower alkoxy group, a lower alkanoyloxy “lower cycloalkenyl group optionally substituted”, “lower group, an aromatic hydrocarbon group, a heterocyclic group, alkynyl group optionally substituted', 'aromatic hydrocar a lower alkylthio group, a lower alkylsulfinyl group, a lower bon group optionally substituted” and "heterocyclic group alkylsulfonyl group or an arylthio group. optionally substituted for Y, the “substituent” for X' 0648. For the above-mentioned "heterocyclic group” in described above can be referred to. the term "heterocyclic group optionally substituted for Z, the 0634) ForY.Y',Y andY', groups described below "heterocyclic group' described above can be referred to. can be referred to. 0649. For the substituent in the terms “lower alkyl group 0635. For the “ring structure” represented by Y's together optionally substituted”, “lower cycloalkyl group optionally with the carbon which is bonded with each other, the same substituted”, “lower alkenyl group optionally substituted’, structures as the above-mentioned “ring structure' repre “lower cycloalkenyl group optionally substituted”, “lower sented by X's together with the carbon which is bonded with alkynyl group optionally substituted and "heterocyclic each other are mentioned. group optionally substituted” for Z, the “substituents” for X' 0636. In the compound (I), Z represents a cyano group, a described above can be referred to. lower alkyl group optionally Substituted, a higher alkyl group, 0650 For Q', Z', Z, Q, Z, Z, Z, Z, Z, Z and Z, a lower cycloalkyl group optionally substituted, a lower alk groups described later can be referred to. enyl group optionally substituted, a higher alkenyl group, a 0651) X4, X-12, X13, X44, Y41, Y42, Y43, Y44 and 74 lower cycloalkenyl group optionally Substituted, a lower represent each independently a lower alkyl group optionally alkynyl group optionally substituted, a higher alkynyl group, Substituted, a higher alkyl group, a lower cycloalkyl group an aromatic hydrocarbon group optionally substituted, a het optionally Substituted, a lower alkenyl group optionally Sub erocyclic group optionally substituted, C(=Q')Z, C(=O) stituted, a higher alkenyl group, a lower cycloalkenyl group OZ’, C( Q?)NZZ, SOZ, NZZ, OZ’ or N. C(Z), optionally substituted, a lower alkynyl group optionally sub 0637 and preferably mentioned is an aromatic hydrocar stituted, a higher alkynyl group, an aromatic hydrocarbon bon group optionally substituted, heterocyclic group option group optionally Substituted or a heterocyclic group option ally substituted or SO.Z (wherein, Z is an aromatic hydro ally substituted. carbon group optionally substituted), and particularly 0652 For the above-mentioned “lower alkyl group' in the preferably mentioned is an aromatic hydrocarbon group term “lower alkyl group optionally substituted” for X', X', optionally substituted, heterocyclic group or SOZ X,X,Y',Y',Y, Y- and Z, the “lower alkyl group” (wherein, Z is an aromatic hydrocarbon group). described above can be referred to. 0638 For the above-mentioned “lower alkyl group' in the 0653 For the above-mentioned “lower cycloalkyl group' term “lower alkyl group optionally substituted for Z, the in the term “lower cycloalkyl group optionally substituted “lower alkyl group' described above can be referred to. for X1, X1, X1,X'Y1, Y1, Y1, Y- and Z', the “lower 0639 For the above-mentioned “higher alkyl group' for cycloalkyl group' described above can be referred to. Z, the “higher alkyl group' described above can be referred 0654 For the above-mentioned “lower alkenyl group' in tO. the term “lower alkenyl group optionally substituted for 0640 For the above-mentioned “lower cycloalkyl group' X1, X-12, X43, X44, Y41, Y12, Y43, Y44 and Z1, the “lower in the term “lower cycloalkyl group optionally substituted alkenyl group' described above can be referred to. for Z, the “lower cycloalkyl group' described above can be 0655 For the above-mentioned “lower cycloalkenyl referred to. group' in the term “lower cycloalkenyl group optionally Sub 0641 For the above-mentioned “lower alkenyl group' in stituted for X1, X1, X1, X1, Y1, Y1, Y1, Y14 and Z1, the term “lower alkenyl group optionally substituted for Z. the “lower cycloalkenyl group' described above can be the “lower alkenyl group' described above can be referred to. referred to. 0642 For the above-mentioned “higher alkenyl group' for 0656. For the above-mentioned “lower alkenyl group' in Z, the “higher alkenyl group' described above can be referred the term “lower alkynyl group optionally substituted for tO. X1, X1, X1, X1, Y1, Y1, Y1, Y14 and Z1, the “lower 0643 For the above-mentioned “lower cycloalkenyl alkenyl group' described above can be referred to. group' in the term “lower cycloalkenyl group optionally Sub 0657 For the above-mentioned “aromatic hydrocarbon stituted for Z, the “lower cycloalkenyl group' described group' in the term 'aromatic hydrocarbon group optionally above can be referred to. substituted for X1, X1, X1, X1, Y1, Y1, Y1, Y-1 and 0644. For the above-mentioned “lower alkynyl group' in Z", the "aromatic hydrocarbon group” described above can the term “lower alkynyl group optionally substituted for Z. be referred to. the “lower alkynyl group' described above can be referred to. 0658. For the above-mentioned "heterocyclic group” in 0645. For the above-mentioned “higher alkynyl group' for the term "heterocyclic group optionally substituted” for X', Z, the “higher alkynyl group' described above can be referred X1, X1, X',Y, Y-3, Y, Y- and Z', the “heterocyclic tO. group' described above can be referred to. 0646 For the above-mentioned “aromatic hydrocarbon 0659 For the “substituent” in the terms “lower alkyl group group' in the term 'aromatic hydrocarbon group optionally optionally substituted”, “lower cycloalkyl group optionally US 2011/0319437 A1 Dec. 29, 2011 substituted”, “lower alkenyl group optionally substituted’, a heterocyclic group optionally Substituted, an acyl group “lower cycloalkenyl group optionally substituted”, “lower optionally substituted, a carbamoyl group optionally Substi alkynyl group optionally substituted', 'aromatic hydrocar tuted or a group represented by —SOR (wherein, R repre bon group optionally substituted” and "heterocyclic group sents a lower alkyl group optionally Substituted, higher alkyl optionally substituted” forX, X,X,X,Y',Y',Y', group, lower cycloalkyl group optionally substituted, lower Y''' and Z', the “substituents” for X' describe above can be alkenyl group optionally Substituted, higher alkenyl group, referred to. lower cycloalkenyl group optionally substituted, lower alky 0660 X, X2, X53, X54, YBl, YB2, YB5, Y and Z nyl group optionally Substituted, higher alkynyl group, or represent each independently a lower alkyl group optionally aromatic hydrocarbon group optionally Substituted). Substituted, a higher alkyl group, a lower cycloalkyl group 0670 For the above-mentioned “lower alkyl group' in the optionally Substituted, a lower alkenyl group optionally Sub term “lower alkyl group optionally substituted as a substitu stituted, a higher alkenyl group, a lower cycloalkenyl group ent on "amino group optionally substituted, the “lower alkyl optionally Substituted, a lower alkynyl group optionally Sub group' described above can be referred to. stituted, a higher alkynyl group, an aromatic hydrocarbon 0671 For the above-mentioned “lower cycloalkyl group' group optionally Substituted, a heterocyclic group optionally in the term “lower cycloalkyl group optionally substituted as Substituted or an amino group optionally substituted. a Substituent on "amino group optionally Substituted, the 0661 For the above-mentioned “lower alkyl group' in the “lower cycloalkyl group' described above can be referred to. term “lower alkyl group optionally substituted” for X', X’, 0672 For the above-mentioned “lower alkenyl group' in X3, X,Y,Y, Y-3, Y and Z, the “lower alkyl group the term “lower alkenyl group optionally substituted as a described above can be referred to. Substituent on "amino group optionally substituted’, the 0662 For the above-mentioned “lower cycloalkyl group' “lower alkenyl group' described above can be referred to. in the term “lower cycloalkyl group optionally substituted 0673 For the above-mentioned “lower cycloalkenyl forX, X2, X3, Xt,Yt. 1,YP2,YP3, Yi and Z?, the “lower group' in the term “lower cycloalkenyl group optionally Sub cycloalkyl group' described above can be referred to. stituted as a Substituent on "amino group optionally substi 0663 For the above-mentioned “lower alkenyl group' in tuted, the “lower cycloalkenyl group' described above can the term “lower alkenyl group optionally substituted for be referred to. X?, X2, X3, Xt,Yt. 1, Y12, Y-3, YP4 and Z?, the “lower 0674) For the above-mentioned “lower alkenyl group' in alkenyl group' described above can be referred to. the term “lower alkenyl group optionally substituted as a 0664 For the above-mentioned “lower cycloalkenyl substituent on "amino group optionally substituted, the group' in the term “lower cycloalkenyl group optionally Sub “lower alkenyl group' described above can be referred to. stituted for X?, X2, X3, Xt,Yt. 1, Y12, YP3, YP4 and Z?, 0675 For the above-mentioned “aromatic hydrocarbon the “lower cycloalkenyl group' described above can be group' in the term 'aromatic hydrocarbon group optionally referred to. Substituted as a Substituent on "amino group optionally Sub 0665 For the above-mentioned “lower alkenyl group' in stituted, the 'aromatic hydrocarbon group' described above the term “lower alkynyl group optionally substituted” for X', can be referred to. X2, X3, X,Y,Y72, Yi, Yand Z, the “lower alkenyl 0676 For the above-mentioned "heterocyclic group” in group' described above can be referred to. the term "heterocyclic group optionally substituted as a sub 0666 For the above-mentioned “aromatic hydrocarbon stituent on "amino group optionally substituted, the "hetero group' in the term 'aromatic hydrocarbon group optionally cyclic group' described above can be referred to. substituted for X1,X2, X's, X, Y, Y-2,Y, Y- and 0677 For the “substituent” in the terms “lower alkyl group Z’, the “aromatic hydrocarbon group' described above can optionally substituted”, “lower cycloalkyl group optionally be referred to. substituted”, “lower alkenyl group optionally substituted’, 0667 For the above-mentioned "heterocyclic group” in “lower cycloalkenyl group optionally substituted”, “lower the term "heterocyclic group optionally substituted” for X', alkynyl group optionally Substituted', 'aromatic hydrocar X2, X, X,Y,Y,Y, Y- and Z, the “heterocyclic bon group optionally substituted” and "heterocyclic group group' described above can be referred to. optionally Substituted as a Substituent on "amino group 0668 For the “substituent in the terms “lower alkyl group optionally substituted”, the “substituents” for X" describe optionally substituted”, “lower cycloalkyl group optionally above can be referred to. substituted”, “lower alkenyl group optionally substituted’, 0678. The “substituent on “acyl group optionally substi “lower cycloalkenyl group optionally substituted”, “lower tuted includes, when this acyl group is a lower alkanoyl alkynyl group optionally substituted', 'aromatic hydrocar group or a lower alkoxy carbonyl group, bon group optionally substituted” and "heterocyclic group 0679 for example, a lower alkylthiogroup (e.g., Calky optionally substituted forX, X2, X3, X,Y,Y, Y-3, lthio groups such as methylthio, ethylthio, n-propylthio, iso Y?" and Z’, the “substituents” for X' describe above can be propylthio, isobutylthio and the like), a halogen, a lower referred to. alkoxy group, a nitro group, a lower alkoxycarbonyl group, an 0669. The above-mentioned “amino group optionally sub alkoxyimino group (e.g., C alkoxyimino groups such as stituted for X?, X2, X3, Xt,Yt. 1, Y12, Y-3, Y/4 and Z? methoxyimino, ethoxyimino, n-propoxyimino, tert-butoxy represents a mono or diamino group optionally substituted imino, n-hexyloxy-imino and the like), and a hydroxyimino with a lower alkyl group optionally substituted, a higher alkyl group. The number of Substituents is in a substitutable range group, a lower cycloalkyl group optionally Substituted, a and 1 to 5, preferably 1 to 3. lower alkenyl group optionally Substituted, a higher alkenyl 0680 When this acyl group is an aroyl group, an aryloxy group, a lower cycloalkenyl group optionally substituted, a carbonyl group, an aryl lower alkanoyl group, an aryl lower lower alkynyl group optionally Substituted, a higher alkynyl alkoxycarbonyl group, a 5 to 6-membered heterocyclic car group, an aromatic hydrocarbon group optionally Substituted, bonyl group or a 5 to 6-membered heterocyclic acetyl group, US 2011/0319437 A1 Dec. 29, 2011 32

0681 the “substituent includes, for example, a lower substituted”, “lower alkenyl group optionally substituted’, alkyl group, a lower cycloalkyl group, a lower alkenyl group, “lower cycloalkenyl group optionally substituted”, “lower a lower cycloalkenyl group, a lower alkynyl group, a lower alkynyl group optionally Substituted', 'aromatic hydrocar alkoxy group, an acyl group, a nitro group, an amino group, a bon group optionally substituted” and "heterocyclic group hydroxyl group, a cyano group, a Sulfamoyl group, a mer optionally substituted”, the “substituents” for X' described capto group, a halogen, a lower alkylthio group (e.g., C. above can be referred to. alkylthio groups such as methylthio, ethylthio, n-propylthio. 0695. As the “amino group optionally substituted, the isobutylthio and the like) and the like. The number of sub same “amino groups optionally Substituted as exemplified stituents is in a substitutable range and 1 to 5, preferably 1 to for X1,X2, X3, X, Y, YP2, YP3 YP4 and Z? are men 3. tioned. 0682. The “substituent on “carbamoyl group optionally (0696. The “ring structure” represented by XP and X', substituted includes a lower alkyl group, a lower cycloalkyl XP and X2, XD and XP, XP and X-Y P and Y, Y-D2 group, a lower alkenyl group, a lower cycloalkenyl group, a and Yi, YP and Yi, YP and Y, and ZP and Z together lower alkynyl group, an aromatic hydrocarbon group, a het with the nitrogen which is bonded with each other means a 3 erocyclic group and an acyl group. to 8-membered heterocyclic group composed of the nitrogen 0683. The “carbamoyl group' is optionally substituted atom as a ring constituent atom, and mentioned are 3 to with one or two substituent(s) described above. 8-membered (preferably, 5 to 6-membered) nitrogen-con 0684 XP, XP, XP, XP, YP', YP2, YP3, YP4 and ZP taining heterocyclic groups composed of the nitrogenatom as represent each independently a hydrogenatom, a lower alkyl a ring constituent atom, and optionally having 1 to 3 hetero group optionally substituted, a higher alkyl group, a lower atoms Such as a nitrogenatom optionally oxidized, an oxygen cycloalkyl group optionally substituted, a lower alkenyl atom, a Sulfur atom optionally mono or di-oxidized, and the group optionally substituted, a higher alkenyl group, a lower like Such as, for example, 11-aziridinyl, 11-azirinyl, cycloalkenyl group optionally Substituted, a lower alkynyl 11-aZetyl, 1-aZetydinyl, 1-perhydroaZepynyl, 1-perhydroa group optionally substituted, a higher alkynyl group, an aro ZoSynyl, 1-pyrrolidinyl, 1-pyrrolinyl, 1-pyrrolyl, 1-pyrazolyl, matic hydrocarbon group optionally Substituted, a heterocy 1-imidazolyl, 1,2,3-triazol-1- or 2-yl, I,2,4-triazol-1- or 4-yl, clic group optionally substituted, an amino group optionally 1H-tetrazol-1-yl, 2H-tetrazol-2-yl, 1-piperidinyl, 4-thiomor substituted, a cyano group or OG', and pholinyl, 4-morpholinyl, 1-dihydropyridyl, 1-tetrahydropy 0685 XEl, XE2, XE3, XE4, YEl, YE2, YES, YE4 and ZE ridyl, 2- or 4-oxodihydropyridin-1-yl, 1-tetrahydropyrim represent each independently a hydrogenatom, a lower alkyl idyl, 1-perhydropyrimidyl, 1-dihydrotriazinyl, group optionally substituted, a higher alkyl group, a lower 1-tetrahydrotriazinyl, 2-oxodihydrotriazin-1-yl, 1,4-oxazin cycloalkyl group optionally substituted, a lower alkenyl 4-yl, 1.4-thiazin-4-yl, 1.3-thiazin-3-yl, 1-piperazinyl, 1-per group optionally substituted, a higher alkenyl group, a lower hydropyridazinyl, indol-1-yl, indolin-1-yl, isoindol-2-yl, cycloalkenyl group optionally Substituted, a lower alkynyl isoindolin-2-yl, 1H-indazol-1-yl, 2,3-dihydrobenzoxazol-3- group optionally substituted, a higher alkynyl group, an aro y1, 2,3-dihydrobenzothiazol-3-yl, benzotriazol-1-yl, 7-puri matic hydrocarbon group optionally Substituted, or a hetero nyl, 9-carbazoyl and the like; and groups obtained by con cyclic group optionally Substituted, densing a benzene ring or 3 to 8-membered (preferably, 5 to 0686 alternatively, XP and X', X’ and X, XP and 6-membered) heterocyclic group (the heterocyclic group has XP, XP and XP, YP and YE1,YP2 and YE2, YP3 and YES, 1 to 4 nitrogen atom(s) optionally oxidized, oxygen atom(s), YandY''' and Z' and Z representaring structure together or sulfur atom(s) optionally mono or di-oxidized) with the with the nitrogen which is bonded with each other. above-mentioned nitrogen-containing heterocyclic group. 0687. For the “lower alkyl group” in the term “lower alkyl 0697 The “3 to 8-membered heterocyclic group com group optionally substituted’, the “lower alkyl group' posed of the nitrogenatom as a ring constituent atom' may be described above can be referred to. substituted with the same substituent as exemplified for the 0688. For the “lower cycloalkyl group” in the term “lower Substituent on 'aromatic hydrocarbon group optionally Sub cycloalkyl group optionally substituted, the “lower stituted for X'. The number of the substituent is in a substi cycloalkyl group' described above can be referred to. tutable range and 1 to 5, preferably 1 to 3. 0689 For the “lower alkenyl group” in the term “lower 0698 XF1, XF2, XF3, XF4, YF, XF2, YF3, Y and ZF alkenyl group optionally substituted, the “lower alkenyl represent each independently a lower alkyl group optionally group' described above can be referred to. Substituted, a higher alkyl group, a lower cycloalkyl group (0690. For the “lower cycloalkenyl group” in the term optionally Substituted, a lower alkenyl group optionally Sub “lower cycloalkenyl group optionally substituted, the “lower stituted, a higher alkenyl group, a lower cycloalkenyl group cycloalkenyl group' described above can be referred to. optionally Substituted, a lower alkynyl group optionally Sub (0691 For the “lower alkynyl group” in the term “lower stituted, a higher alkynyl group, an aromatic hydrocarbon alkynyl group optionally substituted, the “lower alkynyl group optionally Substituted, a heterocyclic group optionally group' described above can be referred to. Substituted, or an amino group optionally Substituted. 0692 For the “aromatic hydrocarbon group” in the term (0699 For the “lower alkyl group” in the term “lower alkyl “aromatic hydrocarbon group optionally substituted, the group optionally substituted’, the “lower alkyl group' “aromatic hydrocarbon group' described above can be described above can be referred to. referred to. (0700 For the “lower cycloalkyl group” in the term “lower (0693 For the “heterocyclic group” in the term “heterocy cycloalkyl group optionally substituted, the “lower clic group optionally substituted’, the "heterocyclic group' cycloalkyl group' described above can be referred to. described above can be referred to. (0701 For the “lower alkenyl group” in the term “lower 0694 For the “substituent in the terms “lower alkyl group alkenyl group optionally substituted, the “lower alkenyl optionally substituted”, “lower cycloalkyl group optionally group' described above can be referred to. US 2011/0319437 A1 Dec. 29, 2011

0702 For the “lower cycloalkenyl group' in the term 0716 For the “aromatic hydrocarbon group” in the term “lower cycloalkenyl group optionally substituted, the “lower “aromatic hydrocarbon group optionally substituted, the cycloalkenyl group' described above can be referred to. “aromatic hydrocarbon group' described above can be (0703 For the “lower alkynyl group” in the term “lower referred to. alkynyl group optionally substituted, the “lower alkynyl 0717 For the “heterocyclic group” in the term “heterocy group' described above can be referred to. clic group optionally substituted’, the "heterocyclic group' 0704. For the “aromatic hydrocarbon group” in the term described above can be referred to. “aromatic hydrocarbon group optionally substituted, the 0718 For the “substituent” in the terms “lower alkyl group “aromatic hydrocarbon group' described above can be optionally substituted”, “lower cycloalkyl group optionally referred to. substituted”, “lower alkenyl group optionally substituted’, (0705 For the “heterocyclic group” in the term “heterocy “lower cycloalkenyl group optionally substituted”, “lower clic group optionally substituted’, the "heterocyclic group' alkynyl group optionally Substituted', 'aromatic hydrocar described above can be referred to. bon group optionally substituted” and "heterocyclic group (0706 For the “substituent” in the terms “lower alkyl group optionally substituted, the “substituents” for X described optionally substituted”, “lower cycloalkyl group optionally above can be referred to. substituted”, “lower alkenyl group optionally substituted’, 0719. For the “ring structure” represented by X' and “lower cycloalkenyl group optionally substituted”, “lower XHXC2 and XH2, XG7 and XF7, YC2 and YH2,YG6 and YH6 alkynyl group optionally substituted', 'aromatic hydrocar and Z and Z' together with the nitrogen which is bonded bon group optionally substituted” and "heterocyclic group with each other, the same structures as the above-mentioned optionally substituted”, the “substituents” for X' described “ring structure” represented by XP and X, XP and X’, above can be referred to. XP and X3, XP and X-YP and YE1, Y2 and YF2, YP 0707. As the “amino group optionally substituted, the and Y, YP and Y, and ZP and Z together with the same “amino groups optionally Substituted as exemplified nitrogen which is bonded with each other are mentioned. for X?, X2, X3, Xt,Yt. 1, Y12, YP3, Yi and Z7 are men 0720 X', X, Y, Y and Z represent each indepen tioned. dently a hydrogen atom, a lower alkyl group optionally Sub (0708) X, X2, X7, Y?, Y and Z represent each stituted, a higher alkyl group, a lower cycloalkyl group independently a hydrogen atom, a lower alkyl group option optionally Substituted, a lower alkenyl group optionally Sub ally Substituted, a higher alkyl group, a lower cycloalkyl stituted, a higher alkenyl group, a lower cycloalkenyl group group optionally Substituted, a lower alkenyl group option optionally substituted, a lower alkynyl group optionally sub ally substituted, a higher alkenyl group, a lower cycloalkenyl stituted, a higher alkynyl group, an aromatic hydrocarbon group optionally Substituted, a lower alkynyl group option group optionally Substituted, a heterocyclic group optionally ally Substituted, a higher alkynyl group, an aromatic hydro substituted, OG, SG", or NG'G', carbon group optionally Substituted, a heterocyclic group 0721 alternatively, representaring structure together with optionally substituted, C(=Q')G', C(=O)CQ', the carbon which is bonded with each other. C(-Q')NGP'G' or SOG', and 0722. For G', G', G' and G', descriptions below can 0709 X, X2, X7, Yi, Y and Z represent each be referred to. independently a hydrogen atom, a lower alkyl group option ally Substituted, a higher alkyl group, a lower cycloalkyl 0723. For the “lower alkyl group” in the term “lower alkyl group optionally Substituted, a lower alkenyl group option group optionally substituted’, the “lower alkyl group' ally substituted, a higher alkenyl group, a lower cycloalkenyl described above can be referred to. group optionally Substituted, a lower alkynyl group option 0724 For the “lower cycloalkyl group' in the term “lower ally Substituted, a higher alkynyl group, an aromatic hydro cycloalkyl group optionally substituted, the “lower carbon group optionally Substituted, or a heterocyclic group cycloalkyl group' described above can be referred to. optionally substituted, alternatively, X' and X', X’ and 0725 For the “lower alkenyl group” in the term “lower X2, X7 and X7, Y2 andY2,Y6 andYe, and Z and ZH alkenyl group optionally substituted, the “lower alkenyl represent a ring structure together with the nitrogen which is group' described above can be referred to. bonded with each other. 0726 For the “lower cycloalkenyl group” in the term 0710 For Q', G', G, Q’?, GP, GI or G', descrip “lower cycloalkenyl group optionally substituted, the “lower tions below can be referred to. cycloalkenyl group' described above can be referred to. 0711 For the “lower alkyl group” in the term “lower alkyl 0727. For the “lower alkynyl group” in the term “lower group optionally substituted’, the “lower alkyl group' alkynyl group optionally substituted, the “lower alkynyl described above can be referred to. group' described above can be referred to. 0712 For the “lower cycloalkyl group” in the term “lower 0728. For the “aromatic hydrocarbon group” in the term cycloalkyl group optionally substituted, the “lower “aromatic hydrocarbon group optionally substituted, the cycloalkyl group' described above can be referred to. “aromatic hydrocarbon group' described above can be 0713 For the “lower alkenyl group” in the term “lower referred to. alkenyl group optionally substituted, the “lower alkenyl 0729. For the “heterocyclic group” in the term “heterocy group' described above can be referred to. clic group optionally substituted’, the "heterocyclic group' 0714 For the “lower cycloalkenyl group' in the term described above can be referred to. “lower cycloalkenyl group optionally substituted, the “lower (0730. For the “substituent” in the terms “lower alkyl group cycloalkenyl group' described above can be referred to. optionally substituted”, “lower cycloalkyl group optionally 0715 For the “lower alkynyl group” in the term “lower substituted”, “lower alkenyl group optionally substituted’, alkynyl group optionally substituted, the “lower alkynyl “lower cycloalkenyl group optionally substituted”, “lower group' described above can be referred to. alkynyl group optionally Substituted', 'aromatic hydrocar US 2011/0319437 A1 Dec. 29, 2011 34 bon group optionally substituted” and "heterocyclic group 0745. For the “lower alkenyl group” in the term “lower optionally substituted, the “substituents” for X" described alkenyl group optionally substituted, the “lower alkenyl above can be referred to. group' described above can be referred to. (0731. For the “ring structure” represented by X', X,Y, 0746 For the “lower cycloalkenyl group” in the term Y' and Z together with the carbon which is bonded with each “lower cycloalkenyl group optionally substituted, the “lower other, the same structures as the above-mentioned “ring struc cycloalkenyl group' described above can be referred to. ture” represented by X's together with the carbon which is 0747 For the “lower alkynyl group” in the term “lower bonded with each other are mentioned. alkenyl group optionally substituted, the “lower alkenyl (0732 X*, Y’ and Z' represent each independently a group' described above can be referred to. lower alkyl group optionally Substituted, a higher alkyl group, 0748. For the “aromatic hydrocarbon group” in the term a lower cycloalkyl group optionally substituted, a lower alk “aromatic hydrocarbon group optionally substituted, the enyl group optionally substituted, a higher alkenyl group, a “aromatic hydrocarbon group' described above can be lower cycloalkenyl group optionally Substituted, a lower referred to. alkynyl group optionally substituted, a higher alkynyl group, 0749 For the “heterocyclic group” in the term “heterocy an aromatic hydrocarbon group optionally substituted, a het clic group optionally substituted’, the "heterocyclic group' erocyclic group optionally substituted, C(=Q')G'. described above can be referred to. C(O)OG, C( Q^2)NG G2 or SOG2. (0750 For the “substituent” in the terms “lower alkyl group 0733 For Q^, G-2, G?, Q^2, G, G2 or G?, descrip optionally substituted”, “lower cycloalkyl group optionally tions below can be referred to. substituted”, “lower alkenyl group optionally substituted’, (0734) For the “lower alkyl group” in the term “lower alkyl “lower cycloalkenyl group optionally substituted”, “lower group optionally substituted’, the “lower alkyl group' alkynyl group optionally Substituted', 'aromatic hydrocar described above can be referred to. bon group optionally substituted” and "heterocyclic group (0735. For the “lower cycloalkyl group” in the term “lower optionally substituted, the “substituents” for X" described cycloalkyl group optionally substituted, the “lower above can be referred to. cycloalkyl group' described above can be referred to. (0751 G', G' and G' represent each independently a (0736. For the “lower alkenyl group” in the term “lower hydrogen atom, a lower alkyl group optionally substituted, a alkenyl group optionally substituted, the “lower alkenyl higher alkyl group, a lower cycloalkyl group optionally Sub group' described above can be referred to. stituted, a lower alkenyl group optionally substituted, a higher 0737 For the “lower cycloalkenyl group” in the term alkenyl group, a lower cycloalkenyl group optionally substi “lower cycloalkenyl group optionally substituted, the “lower tuted, a lower alkynyl group optionally Substituted, a higher cycloalkenyl group' described above can be referred to. alkynyl group, an aromatic hydrocarbon group optionally (0738. For the “lower alkynyl group” in the term “lower Substituted or a heterocyclic group optionally Substituted. alkynyl group optionally substituted, the “lower alkynyl (0752 For the “lower alkyl group” in the term “lower alkyl group' described above can be referred to. group optionally substituted’, the “lower alkyl group' 0739 For the “aromatic hydrocarbon group” in the term described above can be referred to. “aromatic hydrocarbon group optionally substituted, the (0753 For the “lower cycloalkyl group” in the term “lower “aromatic hydrocarbon group' described above can be cycloalkyl group optionally substituted, the “lower referred to. cycloalkyl group' described above can be referred to. 0740 For the "heterocyclic group' in the term "heterocy (0754 For the “lower alkenyl group” in the term “lower clic group optionally substituted’, the "heterocyclic group' alkenyl group optionally substituted, the “lower alkenyl described above can be referred to. group' described above can be referred to. 0741. For the “substituent in the terms “lower alkyl group (0755 For the “lower cycloalkenyl group” in the term optionally substituted”, “lower cycloalkyl group optionally “lower cycloalkenyl group optionally substituted, the “lower substituted”, “lower alkenyl group optionally substituted’, cycloalkenyl group' described above can be referred to. “lower cycloalkenyl group optionally substituted”, “lower (0756. For the “lower alkenyl group” in the term “lower alkynyl group optionally substituted', 'aromatic hydrocar alkynyl group optionally substituted, the “lower alkenyl bon group optionally substituted” and "heterocyclic group group' described above can be referred to. optionally substituted, the “substituents” for X" described 0757. For the “aromatic hydrocarbon group” in the term above can be referred to. “aromatic hydrocarbon group optionally substituted, the 0742 X7, X, Y and Y' represent each indepen “aromatic hydrocarbon group' described above can be dently a hydrogen atom, a lower alkyl group optionally Sub referred to. stituted, a higher alkyl group, a lower cycloalkyl group (0758. For the “heterocyclic group” in the term “heterocy optionally Substituted, a lower alkenyl group optionally Sub clic group optionally substituted’, the "heterocyclic group' stituted, a higher alkenyl group, a lower cycloalkenyl group described above can be referred to. optionally Substituted, a lower alkynyl group optionally Sub (0759 For the “substituent” in the terms “lower alkyl group stituted, a higher alkynyl group, an aromatic hydrocarbon optionally substituted”, “lower cycloalkyl group optionally group optionally Substituted or a heterocyclic group option substituted”, “lower alkenyl group optionally substituted’, ally substituted. “lower cycloalkenyl group optionally substituted”, “lower 0743. For the “lower alkyl group” in the term “lower alkyl alkynyl group optionally Substituted', 'aromatic hydrocar group optionally substituted’, the “lower alkyl group' bon group optionally substituted” and "heterocyclic group described above can be referred to. optionally substituted”, the “substituents” for X' described 0744. For the “lower cycloalkyl group' in the term “lower above can be referred to. cycloalkyl group optionally substituted, the “lower 0760 G' and G' represent each independently a lower cycloalkyl group' described above can be referred to. alkyl group optionally Substituted, a higher alkyl group, a US 2011/0319437 A1 Dec. 29, 2011 lower cycloalkyl group optionally Substituted, a lower alk (0776 For the “heterocyclic group” in the term “heterocy enyl group optionally substituted, a higher alkenyl group, a clic group optionally substituted’, the "heterocyclic group' lower cycloalkenyl group optionally Substituted, a lower described above can be referred to. alkynyl group optionally substituted, a higher alkynyl group, (0777 For the “substituent” in the terms “lower alkyl group an aromatic hydrocarbon group optionally substituted or a optionally substituted”, “lower cycloalkyl group optionally heterocyclic group optionally Substituted. substituted”, “lower alkenyl group optionally substituted’, 0761 For the “lower alkyl group” in the term “lower alkyl “lower cycloalkenyl group optionally substituted”, “lower group optionally substituted’, the “lower alkyl group' alkynyl group optionally Substituted', 'aromatic hydrocar described above can be referred to. bon group optionally substituted” and "heterocyclic group 0762. For the “lower cycloalkyl group” in the term “lower optionally substituted”, the “substituents” for X' described cycloalkyl group optionally substituted, the “lower above can be referred to. cycloalkyl group' described above can be referred to. 0778. As the “amino group optionally substituted, the 0763 For the “lower alkenyl group” in the term “lower same “amino groups optionally Substituted as exemplified alkenyl group optionally substituted, the “lower alkenyl for X1,X2, X, X, Y, Y-2,Y, Y- and Z are men group' described above can be referred to. tioned. 0764 For the “lower cycloalkenyl group' in the term “lower cycloalkenyl group optionally substituted, the “lower (0779 GP' and G' represent each independently a hydro cycloalkenyl group' described above can be referred to. gen atom, a lower alkyl group optionally Substituted, a higher 0765. For the “lower alkenyl group” in the term “lower alkyl group, a lower cycloalkyl group optionally Substituted, alkynyl group optionally substituted, the “lower alkenyl a lower alkenyl group optionally Substituted, a higher alkenyl group' described above can be referred to. group, a lower cycloalkenyl group optionally substituted, a 0766 For the “aromatic hydrocarbon group” in the term lower alkynyl group optionally Substituted, a higher alkynyl “aromatic hydrocarbon group optionally substituted, the group, an aromatic hydrocarbon group optionally Substituted, “aromatic hydrocarbon group' described above can be a heterocyclic group optionally Substituted, an amino group referred to. optionally substituted, a cyano group or OG', and 0767 For the “heterocyclic group” in the term “heterocy 0780 G' and G' represent each independently a hydro clic group optionally substituted’, the "heterocyclic group' gen atom, a lower alkyl group optionally Substituted, a higher described above can be referred to. alkyl group, a lower cycloalkyl group optionally Substituted, 0768 For the “substituent” in the terms “lower alkyl group a lower alkenyl group optionally Substituted, a higher alkenyl optionally substituted”, “lower cycloalkyl group optionally group, a lower cycloalkenyl group optionally substituted, a substituted”, “lower alkenyl group optionally substituted’, lower alkynyl group optionally Substituted, a higher alkynyl “lower cycloalkenyl group optionally substituted”, “lower group, an aromatic hydrocarbon group optionally Substituted, alkynyl group optionally substituted', 'aromatic hydrocar or a heterocyclic group optionally Substituted, bon group optionally substituted” and "heterocyclic group 0781 alternatively, G' and G', and G' and G' repre optionally substituted”, the “substituents” for X' described sent a ring structure together with the nitrogen which is above can be referred to. bonded with each other. 0769 G' and G' represent each independently a lower 0782. For the “lower alkyl group” in the term “lower alkyl alkyl group optionally Substituted, a higher alkyl group, a group optionally substituted’, the “lower alkyl group' lower cycloalkyl group optionally Substituted, a lower alk described above can be referred to. enyl group optionally substituted, a higher alkenyl group, a 0783 For the “lower cycloalkyl group” in the term “lower lower cycloalkenyl group optionally Substituted, a lower cycloalkyl group optionally substituted, the “lower alkynyl group optionally substituted, a higher alkynyl group, cycloalkyl group' described above can be referred to. an aromatic hydrocarbon group optionally substituted, a het 0784. For the “lower alkenyl group” in the term “lower erocyclic group optionally Substituted or an amino group alkenyl group optionally substituted, the “lower alkenyl optionally substituted. group' described above can be referred to. (0770. For the “lower alkyl group” in the term “lower alkyl group optionally substituted’, the “lower alkyl group' 0785. For the “lower cycloalkenyl group” in the term described above can be referred to. “lower cycloalkenyl group optionally substituted, the “lower (0771) For the “lower cycloalkyl group” in the term “lower cycloalkenyl group' described above can be referred to. cycloalkyl group optionally substituted, the “lower 0786 For the “lower alkynyl group” in the term “lower cycloalkyl group' described above can be referred to. alkynyl group optionally substituted, the “lower alkynyl (0772 For the “lower alkenyl group” in the term “lower group' described above can be referred to. alkenyl group optionally substituted, the “lower alkenyl 0787 For the “aromatic hydrocarbon group” in the term group' described above can be referred to. “aromatic hydrocarbon group optionally substituted, the (0773 For the “lower cycloalkenyl group” in the term “aromatic hydrocarbon group' described above can be “lower cycloalkenyl group optionally substituted, the “lower referred to. cycloalkenyl group' described above can be referred to. 0788 For the “heterocyclic group” in the term “heterocy (0774 For the “lower alkenyl group” in the term “lower clic group optionally substituted’, the "heterocyclic group' alkynyl group optionally substituted, the “lower alkenyl described above can be referred to. group' described above can be referred to. 0789 For the “substituent” in the terms “lower alkyl group 0775 For the “aromatic hydrocarbon group” in the term optionally substituted”, “lower cycloalkyl group optionally “aromatic hydrocarbon group optionally substituted, the substituted”, “lower alkenyl group optionally substituted’, “aromatic hydrocarbon group' described above can be “lower cycloalkenyl group optionally substituted”, “lower referred to. alkynyl group optionally Substituted', 'aromatic hydrocar US 2011/0319437 A1 Dec. 29, 2011 36 bon group optionally substituted” and "heterocyclic group clic group optionally substituted, C(=Q') G"', C(=O) optionally substituted, the “substituents” for X" described OG-1, C( Q)NG-G-1 or SOG-1, and above can be referred to. (0803 G' represents a hydrogen atom, a lower alkyl 0790. As the “amino group optionally substituted, the group optionally Substituted, a higher alkyl group, a lower same “amino groups optionally Substituted as exemplified cycloalkyl group optionally substituted, a lower alkenyl for X?, X2, X3, Xt,Yt. 1, Y12, YP3, Yi and Z7 are men group optionally substituted, a higher alkenyl group, a lower tioned. cycloalkenyl group optionally Substituted, a lower alkynyl 0791) For the “ring structure” represented by G' and G', group optionally substituted, a higher alkynyl group, an aro and G' and G' together with the nitrogen which is bonded matic hydrocarbon group optionally Substituted or a hetero with each other, the same structures as the above-mentioned cyclic group optionally Substituted, “ring structure” formed by XP and X, XP and X, XP (0804) alternatively, G' and G' representaring structure and X3, XP and X, Y and Y1, Y2 and Y?, YP and Y, Y- and Y and Z and Z' together with the nitrogen together with the nitrogen which is bonded with each other. which is bonded with each other are mentioned. (0805 For the “lower alkyl group” in the term “lower alkyl 0792 G' and G' represent each independently a lower group optionally substituted’, the “lower alkyl group' alkyl group optionally Substituted, a higher alkyl group, a described above can be referred to. lower cycloalkyl group optionally Substituted, a lower alk (0806. For the “lower cycloalkyl group” in the term “lower enyl group optionally substituted, a higher alkenyl group, a cycloalkyl group optionally substituted, the “lower lower cycloalkenyl group optionally Substituted, a lower cycloalkyl group' described above can be referred to. alkynyl group optionally substituted, a higher alkynyl group, (0807 For the “lower alkenyl group” in the term “lower an aromatic hydrocarbon group optionally substituted, a het alkenyl group optionally substituted, the “lower alkenyl erocyclic group optionally Substituted, or an amino group group' described above can be referred to. optionally substituted. 0808 For the “lower cycloalkenyl group” in the term 0793. For the “lower alkyl group” in the term “lower alkyl “lower cycloalkenyl group optionally substituted, the “lower group optionally substituted’, the “lower alkyl group' cycloalkenyl group' described above can be referred to. described above can be referred to. (0809 For the “lower alkynyl group” in the term “lower 0794. For the “lower cycloalkyl group” in the term “lower alkynyl group optionally substituted, the “lower alkynyl cycloalkyl group optionally substituted, the “lower group' described above can be referred to. cycloalkyl group' described above can be referred to. 0810 For the “aromatic hydrocarbon group” in the term 0795 For the “lower alkenyl group” in the term “lower “aromatic hydrocarbon group optionally substituted, the alkenyl group optionally substituted, the “lower alkenyl “aromatic hydrocarbon group' described above can be group' described above can be referred to. referred to. 0796. For the “lower cycloalkenyl group” in the term 0811 For the "heterocyclic group' in the term "heterocy “lower cycloalkenyl group optionally substituted, the “lower clic group optionally substituted’, the "heterocyclic group' cycloalkenyl group' described above can be referred to. described above can be referred to. 0797 For the “lower alkynyl group” in the term “lower 0812 For the “substituent in the terms “lower alkyl group alkynyl group optionally substituted, the “lower alkynyl optionally substituted”, “lower cycloalkyl group optionally group' described above can be referred to. substituted”, “lower alkenyl group optionally substituted’, 0798 For the “aromatic hydrocarbon group” in the term “lower cycloalkenyl group optionally substituted”, “lower “aromatic hydrocarbon group optionally substituted, the alkynyl group optionally Substituted', 'aromatic hydrocar “aromatic hydrocarbon group' described above can be bon group optionally substituted” and "heterocyclic group referred to. optionally substituted, the “substituents” for X" described 0799 For the “heterocyclic group” in the term “heterocy above can be referred to. clic group optionally substituted’, the "heterocyclic group' described above can be referred to. 0813 For the “ring structure” represented by G' and G' (0800 For the “substituent” in the terms “lower alkyl group together with the nitrogen which is bonded with each other, optionally substituted”, “lower cycloalkyl group optionally the same structures as the above-mentioned “ring structure' substituted”, “lower alkenyl group optionally substituted’, represented by XP and X', XP and XP, XP and X, XP “lower cycloalkenyl group optionally substituted”, “lower and XP,YP andYEl YP2 andYE2,YP3 andYE3,YP andYE', alkynyl group optionally substituted', 'aromatic hydrocar and ZP and Z together with the nitrogen which is bonded bon group optionally substituted” and "heterocyclic group with each other are mentioned. optionally substituted”, the “substituents” for X' described 0814 For QGa, G41-1, G#1-1, QGP, GDI-1, GEl-l and GF-1, above can be referred to. descriptions below can be referred to. 0801. As the “amino group optionally substituted, the (0815) G' represents a hydrogenatom, a lower alkyl group same “amino groups optionally Substituted as exemplified optionally Substituted, a higher alkyl group, a lower for X1,X2, X, X, Y, Y-12, Y, Y- and Z are men cycloalkyl group optionally substituted, a lower alkenyl tioned. group optionally substituted, a higher alkenyl group, a lower 0802 G' represents a hydrogen atom, a lower alkyl cycloalkenyl group optionally Substituted, a lower alkynyl group optionally substituted, a higher alkyl group, a lower group optionally substituted, a higher alkynyl group, an aro cycloalkyl group optionally substituted, a lower alkenyl matic hydrocarbon group optionally Substituted or a hetero group optionally substituted, a higher alkenyl group, a lower cyclic group optionally Substituted. cycloalkenyl group optionally Substituted, a lower alkynyl 0816. For the “lower alkyl group” in the term “lower alkyl group optionally substituted, a higher alkynyl group, an aro group optionally substituted’, the “lower alkyl group' matic hydrocarbon group optionally Substituted, a heterocy described above can be referred to. US 2011/0319437 A1 Dec. 29, 2011 37

0817 For the “lower cycloalkyl group” in the term “lower 0834) For the “lower alkenyl group” in the term “lower cycloalkyl group optionally substituted, the “lower alkenyl group optionally substituted, the “lower alkenyl cycloalkyl group' described above can be referred to. group' described above can be referred to. 0818. For the “lower alkenyl group” in the term “lower 0835. For the “lower cycloalkenyl group” in the term alkenyl group optionally substituted, the “lower alkenyl “lower cycloalkenyl group optionally substituted, the “lower group' described above can be referred to. cycloalkenyl group' described above can be referred to. 0819 For the “lower cycloalkenyl group' in the term 0836. For the “lower alkynyl group” in the term “lower “lower cycloalkenyl group optionally substituted, the “lower alkynyl group optionally substituted, the “lower alkynyl cycloalkenyl group' described above can be referred to. group' described above can be referred to. 0820. For the “lower alkynyl group” in the term “lower 0837 For the “aromatic hydrocarbon group” in the term alkynyl group optionally substituted, the “lower alkynyl “aromatic hydrocarbon group optionally substituted, the group' described above can be referred to. “aromatic hydrocarbon group' described above can be 0821 For the “aromatic hydrocarbon group” in the term referred to. “aromatic hydrocarbon group optionally substituted, the 0838 For the "heterocyclic group' in the term "heterocy “aromatic hydrocarbon group' described above can be clic group optionally substituted’, the "heterocyclic group' referred to. described above can be referred to. 0822. For the "heterocyclic group' in the term "heterocy 0839 For the “substituent” in the terms “lower alkyl group clic group optionally substituted’, the "heterocyclic group' optionally substituted”, “lower cycloalkyl group optionally described above can be referred to. substituted”, “lower alkenyl group optionally substituted’, 0823 G' represents a lower alkyl group optionally sub “lower cycloalkenyl group optionally substituted”, “lower stituted, a higher alkyl group, a lower cycloalkyl group alkynyl group optionally Substituted', 'aromatic hydrocar optionally Substituted, a lower alkenyl group optionally Sub bon group optionally substituted” and "heterocyclic group stituted, a higher alkenyl group, a lower cycloalkenyl group optionally substituted”, the “substituents” for X' described optionally Substituted, a lower alkynyl group optionally Sub above can be referred to. stituted, a higher alkynyl group, an aromatic hydrocarbon 0840. As the “amino group optionally substituted, the group optionally Substituted or a heterocyclic group option same “amino groups optionally Substituted as exemplified ally substituted. for Xi X2, X3, Xt,Yt. 1, YP2, YP3, Yi and Z? are men 0824 For the “lower alkyl group' in the term “lower alkyl tioned. group optionally substituted’, the “lower alkyl group' 10841 G' represents a hydrogen atom, a lower alkyl described above can be referred to. group optionally Substituted, a higher alkyl group, a lower 0825. For the “lower cycloalkyl group” in the term “lower cycloalkyl group optionally substituted, a lower alkenyl cycloalkyl group optionally substituted, the “lower group optionally substituted, a higher alkenyl group, a lower cycloalkyl group' described above can be referred to. cycloalkenyl group optionally Substituted, a lower alkynyl 0826. For the “lower alkenyl group” in the term “lower group optionally substituted, a higher alkynyl group, an aro alkenyl group optionally substituted, the “lower alkenyl matic hydrocarbon group optionally Substituted, a heterocy group' described above can be referred to. clic group optionally substituted, an amino group optionally 0827. For the “lower cycloalkenyl group' in the term Substituted, a cyano group or OL, and “lower cycloalkenyl group optionally substituted, the “lower 0842 G''' represents a hydrogen atom, a lower alkyl cycloalkenyl group' described above can be referred to. group optionally Substituted, a higher alkyl group, a lower 0828 For the “lower alkynyl group” in the term “lower cycloalkyl group optionally substituted, a lower alkenyl alkynyl group optionally substituted, the “lower alkynyl group optionally substituted, a higher alkenyl group, a lower group' described above can be referred to. cycloalkenyl group optionally Substituted, a lower alkynyl 0829. For the “aromatic hydrocarbon group” in the term group optionally substituted, a higher alkynyl group, an aro “aromatic hydrocarbon group optionally substituted, the matic hydrocarbon group optionally Substituted or a hetero “aromatic hydrocarbon group' described above can be cyclic group optionally Substituted, referred to. 0843 alternatively, G' and G''' representaring struc 0830. For the “heterocyclic group” in the term “heterocy ture together with the nitrogen which is bonded with each clic group optionally substituted’, the "heterocyclic group' other. described above can be referred to. 0844. For the “lower alkyl group” in the term “lower alkyl 0831 G' represents a lower alkyl group optionally sub group optionally substituted’, the “lower alkyl group' stituted, a higher alkyl group, a lower cycloalkyl group described above can be referred to. optionally Substituted, a lower alkenyl group optionally Sub 0845 For the “lower cycloalkyl group” in the term “lower stituted, a higher alkenyl group, a lower cycloalkenyl group cycloalkyl group optionally substituted, the “lower optionally Substituted, a lower alkynyl group optionally Sub cycloalkyl group' described above can be referred to. stituted, a higher alkynyl group, an aromatic hydrocarbon 0846. For the “lower alkenyl group' in the term “lower group optionally Substituted, a heterocyclic group optionally alkenyl group optionally substituted, the “lower alkenyl Substituted or an amino group optionally substituted. group' described above can be referred to. 0832 For the “lower alkyl group” in the term “lower alkyl 0847 For the “lower cycloalkenyl group” in the term group optionally substituted’, the “lower alkyl group' “lower cycloalkenyl group optionally substituted, the “lower described above can be referred to. cycloalkenyl group' described above can be referred to. 0833 For the “lower cycloalkyl group” in the term “lower 0848. For the “lower alkynyl group” in the term “lower cycloalkyl group optionally substituted, the “lower alkynyl group optionally substituted, the “lower alkynyl cycloalkyl group' described above can be referred to. group' described above can be referred to. US 2011/0319437 A1 Dec. 29, 2011

0849. For the “aromatic hydrocarbon group” in the term 0863. As the “amino group optionally substituted, the “aromatic hydrocarbon group optionally substituted, the same “amino groups optionally Substituted as exemplified “aromatic hydrocarbon group' described above can be for X1,X2, X, X, Y, Y-2,Y, Y- and Z are men referred to. tioned. 0850. For the “heterocyclic group” in the term “heterocy 0864 L represents a hydrogen atom, a lower alkyl group clic group optionally substituted’, the "heterocyclic group' optionally Substituted, a higher alkyl group, a lower described above can be referred to. cycloalkyl group optionally substituted, a lower alkenyl 0851. For the “substituent” in the terms “lower alkyl group group optionally substituted, a higher alkenyl group, a lower optionally substituted”, “lower cycloalkyl group optionally cycloalkenyl group optionally Substituted, a lower alkynyl substituted”, “lower alkenyl group optionally substituted’, group optionally substituted, a higher alkynyl group, an aro “lower cycloalkenyl group optionally substituted”, “lower matic hydrocarbon group optionally Substituted or a hetero alkynyl group optionally substituted', 'aromatic hydrocar cyclic group optionally Substituted. bon group optionally substituted” and "heterocyclic group 0865 For the “lower alkyl group” in the term “lower alkyl optionally substituted, the “substituents” for X" described group optionally substituted’, the “lower alkyl group' above can be referred to. described above can be referred to. 0852. As the “amino group optionally substituted, the 0866 For the “lower cycloalkyl group' in the term “lower same “amino groups optionally Substituted as exemplified cycloalkyl group optionally substituted, the “lower for X1,X2, X, X, Y, Y-12, Y, Y- and Z are men cycloalkyl group' described above can be referred to. tioned. 0867 For the “lower alkenyl group” in the term “lower 0853 For the “ring structure” represented by G' and alkenyl group optionally substituted, the “lower alkenyl G''' together with the nitrogen which is bonded with each group' described above can be referred to. other, the same structures as the above-mentioned “ring struc ture” represented by XP and X, XP and X, XP and 0868 For the “lower cycloalkenyl group” in the term X3, XP and X-YP and Y, Y-D2 and YF2, YP and YE, “lower cycloalkenyl group optionally substituted, the “lower Y'andY., and Z' and Z together with the nitrogen which cycloalkenyl group' described above can be referred to. is bonded with each other are mentioned. 0869. For the “lower alkynyl group” in the term “lower 0854 G' represents a lower alkyl group optionally sub alkynyl group optionally substituted, the “lower alkynyl stituted, a higher alkyl group, a lower cycloalkyl group group' described above can be referred to. optionally substituted, a lower alkenyl group optionally sub 0870 For the “aromatic hydrocarbon group” in the term stituted, a higher alkenyl group, a lower cycloalkenyl group “aromatic hydrocarbon group optionally substituted', the optionally Substituted, a lower alkynyl group optionally Sub “aromatic hydrocarbon group' described above can be stituted, a higher alkynyl group, an aromatic hydrocarbon referred to. group optionally Substituted, a heterocyclic group optionally 0871. For the “heterocyclic group” in the term “heterocy Substituted or an amino group optionally substituted. clic group optionally substituted’, the "heterocyclic group' 0855 For the “lower alkyl group” in the term “lower alkyl described above can be referred to. group optionally substituted’, the “lower alkyl group' 0872. For the “substituent” in the terms “lower alkyl group described above can be referred to. optionally substituted”, “lower cycloalkyl group optionally 0856. For the “lower cycloalkyl group” in the term “lower substituted”, “lower alkenyl group optionally substituted’, cycloalkyl group optionally substituted, the “lower “lower cycloalkenyl group optionally substituted”, “lower cycloalkyl group' described above can be referred to. alkynyl group optionally Substituted', 'aromatic hydrocar 0857 For the “lower alkenyl group” in the term “lower bon group optionally substituted” and "heterocyclic group alkenyl group optionally substituted, the “lower alkenyl optionally substituted, the “substituents” for X" described group' described above can be referred to. above can be referred to. 0858. For the “lower cycloalkenyl group” in the term O873 11, 12, 21, 22, 31, 32, 4, 42, 51, 52. “lower cycloalkenyl group optionally substituted, the “lower g o 8. 8. 8. 5. S. S. cycloalkenyl group' described above can be referred to. Q' and Q' represent each independently an oxygenatom or 0859 For the “lower alkynyl group” in the term “lower a Sulfur atom. alkynyl group optionally substituted, the “lower alkynyl 0874 m represents an integer of 1 or 2, group' described above can be referred to. 0875 and n, p and q represent each independently an 0860 For the “aromatic hydrocarbon group” in the term integer of 0 or 2. “aromatic hydrocarbon group optionally substituted, the 0876 The compound (I) can be produced, for example, by “aromatic hydrocarbon group' described above can be the following Production Methods 1 to 7. referred to. 0861) For the "heterocyclic group' in the term "heterocy Production Method 1 clic group optionally substituted’, the "heterocyclic group' described above can be referred to. 0877. The compound (I) can be produced by reacting a 0862 For the “substituent in the terms “lower alkyl group compound represented by the formula (II): optionally substituted”, “lower cycloalkyl group optionally substituted”, “lower alkenyl group optionally substituted’, “lower cycloalkenyl group optionally substituted”, “lower (II) alkynyl group optionally substituted', 'aromatic hydrocar MI bon group optionally substituted” and "heterocyclic group X-CHCH-CEN-Z optionally substituted, the “substituents” for X" described above can be referred to. US 2011/0319437 A1 Dec. 29, 2011 39

(wherein, M1 represents a leaving group, and other symbols diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, are as defined above) with a compound represented by the tetrahydrofuran, dioxane and the like, nitriles Such as aceto formula (III): nitrile, propionitrile and the like, acid amides such as dimeth ylformamide, dimethylacetamide and the like, sulfoxides Y H (III) Such as dimethyl Sulfoxide and the like, Sulfones such as (symbols in the formula are as defined above). Sulfolane and the like, phosphoric amides such as hexameth 0878. As the leaving group represented by M', for ylphosphoramide and the like, halogenated hydrocarbons example, halogens, acyloxy groups (Co acyloxy groups Such as dichloromethane, chloroform, 1,2-dichloroethane, such as C. alkylcarbonyloxy groups optionally substituted carbon tetrachloride and the like, aromatic amines such as with 1 to 3 halogen (s) such as a formyloxy group, acetoxy pyridine, picoline, lutidine, quinoline and the like, and mixed group, propionyloxy group, trifluoroacetoxy group and the solvents thereof, water, further, mixed solvents of these com like; Cz-o-benzoyloxy groups optionally substituted with at pounds with water. least one lower alkyl group Such as a benzoyloxy group, 0885. The reaction temperature is usually about -50 to 4-methylbenzoyloxy group and the like; Calkoxycarbony 200° C., preferably about -30 to 150° C. The reaction time is loxy groups such as methoxycarbonyloxy, t-butoxycarbony generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, loxy and the like) or groups represented by the formula: more preferably about 0.1 to 24 hours. RSO, (wherein, R represents a lower alkyl group or a phe 0886. The resultant compound can be separated and/or nyl optionally Substituted with at least one lower alkyl group, purified by means known perse, for example, concentration, and r is an integer of 0, 1 or 2) and the like can be used. concentration under reduced pressure, liquid nature conver 0879. In this reaction, the amount of the compound repre Sion, transference dissolution, Solvent extraction, distillation, sented by the above-mentioned formula (III) is not particu crystallization, re-crystallization, chromatography and the larly restricted, and may be used in large excess amount as a like. solvent, and preferably, it is about 0.8 to 5 equivalents for the compound represented by the formula (II). Production Method 2 0880. A good result may be obtained in some cases by 0887. The compound (I) can be produced by reacting a presence of a base or action of a base before or after the compound represented by the formula (IV): reaction, for the purpose of promoting the reaction and reduc ing by-products. 0881. As such a base, there can be used alcoholates of (IV) alkali metals such as, for example, sodium ethylate, sodium Y methylate, potassium tert-butoxide and the like; organic bases such as, for example, triethylamine, diisopropylethy H-X-CHCH-C=N-Z lamine, pyridine, 4-dimethylaminopyridine, N,N-dimethyla niline and the like; inorganic bases such as, for example, (wherein, XP1 represents O, S, NH or NX, and other sym potassium carbonate, Sodium carbonate, sodium hydroxide, bols are as defined above) with a compound represented by potassium hydroxide, Sodium hydrogen carbonate, potas the formula (V): sium hydrogen carbonate and the like; metal hydrides such as, for example, lithium hydride, Sodium hydride, potassium XP2 -M2 (V) hydride and the like; or organic lithium reagents such as, for (wherein, X represents X, XorX, M represents a leaving example, butyllithium, lithiumdiisopropylamide and the like. group). The amount of the base to be used is not particularly restricted 0888. As the leaving group represented by M, for providing it does not adversely affect the reaction, and it can example, halogens, acyloxy groups (Co acyloxy groups also be used in large excess amount for acting as a solvent such as C. alkylcarbonyloxy groups optionally substituted simultaneously. with 1 to 3 halogen (s) such as a formyloxy group, acetoxy 0882. In this reaction, a salt of a compound represented by group, propionyloxy group, trifluoroacetoxy group and the the formula (III) and a base, previously prepared, can also be like; Cz-o-benzoyloxy groups optionally substituted with at used. least one alkyl group Such as a benzoyloxy group, 4-methyl 0883. As such a salt, alkali metal salts of lithium, sodium benzoyloxy group and the like: C, alkoxycarbonyloxy and potassium, and alkaline earth metal salts of magnesium groups such as methoxycarbonyloxy, t-butoxycarbonyloxy and calcium are suitable, among others. The amount of the and the like) or groups represented by the formula: RSO, salt is not particularly restricted and the salt may be used in (wherein, R represents a lower alkyl group or a phenyl large excess amount, and preferably, it is about 0.8 to 5 optionally substituted with at least one lower alkyl group, and equivalents for the compound represented by the formula (II). r is an integer of 0, 1 or 2) and the like can be used. 0884. This reaction can be carried out using a suitable 0889. In this reaction, the amount of the compound repre Solvent. Such a solvent is not particularly restricted providing sented by the above-mentioned formula (V) is not particularly it does not react with a reaction Substrate, reaction reagent and restricted, and may be used in large excess amount as a product to give a by-product, and those dissolving both the solvent, and preferably, it is about 0.8 to 5 equivalents for the reaction Substrate and the reaction reagent are desirable. Used compound represented by the formula (IV). as Such a solvent are, for example, aliphatic hydrocarbons 0890. A good result may be obtained in some cases by Such as pentane, hexane, heptane, petroleum ether and the presence of a base or action of a base before or after the like, aromatic hydrocarbons such as benzene, toluene, Xylene reaction, for the purpose of promoting the reaction and reduc and the like, esters such as methyl acetate, ethyl acetate, ethyl ing by-products. As such a base, there can be used alcoholates formate, ethyl propionate and the like, ketones such as of alkali metals such as, for example, sodium ethylate, acetone, methyl ethyl ketone and the like, ethers such as Sodium methylate, potassium tert-butoxide and the like; US 2011/0319437 A1 Dec. 29, 2011 40 organic bases such as, for example, triethylamine, diisopro solvent, and preferably, it is about 0.8 to 5 equivalents for the pylethylamine, pyridine, 4-dimethylaminopyridine, N.N- compound represented by the formula (IV). dimethylaniline and the like; inorganic bases such as, for 0896. A good result may be obtained in some cases by example, potassium carbonate, Sodium carbonate, sodium presence of a base or action of a base before or after the hydroxide, potassium hydroxide, Sodium hydrogen carbon reaction, for the purpose of promoting the reaction and reduc ing by-products. As such a base, there can be used alcoholates ate, potassium hydrogen carbonate and the like; metal of alkali metals such as, for example, sodium ethylate, hydrides Such as, for example, lithium hydride, sodium Sodium methylate, potassium tert-butoxide and the like; hydride, potassium hydride and the like; or organic lithium organic bases such as, for example, triethylamine, diisopro reagents such as, for example, butyllithium, lithiumdiisopro pylethylamine, pyridine, 4-dimethylaminopyridine, N.N- pylamide and the like. The amount of the base to be used is not dimethylaniline and the like; inorganic bases such as, for particularly restricted providing it does not adversely affect example, potassium carbonate, Sodium carbonate, sodium the reaction, and it can also be used in large excess amount for hydroxide, potassium hydroxide, Sodium hydrogen carbon acting as a solvent simultaneously. ate, potassium hydrogen carbonate and the like; metal 0891. This reaction can be carried out using a suitable hydrides Such as, for example, lithium hydride, sodium Solvent. Such a solvent is not particularly restricted providing hydride, potassium hydride and the like; or organic lithium it does not react with a reaction Substrate, reaction reagent and reagents such as, for example, butyllithium, lithiumdiisopro product to give a by-product, and those dissolving both the pylamide and the like. The amount of the base to be used is not reaction Substrate and the reaction reagent are desirable. Used particularly restricted providing it does not adversely affect as Such a solvent are, for example, aliphatic hydrocarbons the reaction, and it can also be used in large excess amount for Such as pentane, hexane, heptane, petroleum ether and the acting as a solvent simultaneously. like, aromatic hydrocarbons such as benzene, toluene, Xylene 0897. This reaction can be carried out using a suitable and the like, esters such as methyl acetate, ethyl acetate, ethyl Solvent. Such a solvent is not particularly restricted providing formate, ethyl propionate and the like, ketones such as it does not react with a reaction Substrate, reaction reagent and acetone, methyl ethyl ketone and the like, ethers such as product to give a by-product, and those dissolving both the diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, reaction Substrate and the reaction reagent are desirable. Used tetrahydrofuran, dioxane and the like, nitriles Such as aceto as Such a solvent are, for example, aliphatic hydrocarbons nitrile, propionitrile and the like, acid amides such as dimeth Such as pentane, hexane, heptane, petroleum ether and the ylformamide, dimethylacetamide and the like, sulfoxides like, aromatic hydrocarbons such as benzene, toluene, Xylene Such as dimethyl Sulfoxide and the like, Sulfones such as and the like, esters such as methyl acetate, ethyl acetate, ethyl sulfolane and the like, phosphoric amides such as hexameth formate, ethyl propionate and the like, ketones such as ylphosphoramide and the like, halogenated hydrocarbons acetone, methyl ethyl ketone and the like, ethers such as Such as dichloromethane, chloroform, 1,2-dichloroethane, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, carbon tetrachloride and the like, aromatic amines such as tetrahydrofuran, dioxane and the like, nitriles Such as aceto pyridine, picoline, lutidine, quinoline and the like, and mixed nitrile, propionitrile and the like, acid amides such as dimeth solvents thereof, water, further, mixed solvents of these com ylformamide, dimethylacetamide and the like, sulfoxides pounds with water. Such as dimethyl Sulfoxide and the like, Sulfones such as 0892. The reaction temperature is usually about -50 to Sulfolane and the like, phosphoric amides such as hexameth 200° C., preferably about -30 to 150° C. The reaction time is ylphosphoramide and the like, halogenated hydrocarbons generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, Such as dichloromethane, chloroform, 1,2-dichloroethane, more preferably about 0.1 to 24 hours. carbon tetrachloride and the like, aromatic amines such as 0893. The resultant compound can be separated and/or pyridine, picoline, lutidine, quinoline and the like, and mixed purified by means known perse, for example, concentration, solvents thereof, water, further, mixed solvents of these com concentration under reduced pressure, liquid nature conver pounds with water. Sion, transference dissolution, solvent extraction, distillation, 0898. The reaction temperature is usually about -50 to crystallization, re-crystallization, chromatography and the 200° C., preferably about -30 to 150° C. The reaction time is like. generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, more preferably about 0.1 to 24 hours. 0899. The resultant compound can be separated and/or Production Method 3 purified by means known perse, for example, concentration, 0894. The compound (I) can be produced by reacting a concentration under reduced pressure, liquid nature conver compound represented by the formula (VI): Sion, transference dissolution, Solvent extraction, distillation, crystallization, re-crystallization, chromatography and the like. (VI) Y Production Method 4 H-CHSCH-CEN-Z 0900. The compound (I) can be produced by hydrogenat ing a compound represented by the formula (IIX): (wherein, symbols are as defined above) with a compound represented by the formula (VII): (IDX) Y X H (VII) (wherein, symbols are as defined above). X-CHEC-CEN-Z 0895. In this reaction, the amount of the compound repre sented by the above-mentioned formula (VII) is not particu (wherein, symbols are as defined above). As the hydrogenat larly restricted, and may be used in large excess amount as a ing reagent, a hydrogen gas, formic acid, hydride reagents US 2011/0319437 A1 Dec. 29, 2011

(e.g., Sodium borohydride, potassium borohydride, sodium (0907. As the leaving group represented by M, for cyanoborohydride and the like) can be used. example, halogens, acyloxy groups (Co acyloxy groups 0901. In this reaction, the amount of the above-mentioned Such as C. alkylcarbonyloxy groups optionally Substituted hydrogenating reagent is not particularly restricted, and may with 1 to 3 halogen (s) such as a formyloxy group, acetoxy be used in large excess amount, and preferably, it is about 0.8 group, propionyloxy group, trifluoroacetoxy group and the to 5 equivalents. like; Cz--benzoyloxy groups optionally substituted with at 0902. A good result may be obtained in some cases by least one lower alkyl group Such as a benzoyloxy group, using a catalyst, for the purpose of promoting the reaction and 4-methylbenzoyloxy group and the like; Calkoxycarbony reducing by-products. As such a catalyst, for example, tran loxy groups such as methoxycarbonyloxy, t-butoxycarbony sition metal catalysts such as palladium-carbon, palladium loxy and the like), lower alkoxy groups (C. alkoxy groups barium sulfate, Lindlar catalyst (palladium-calcium carbon Such as methoxy group, ethoxy group, propoxy group and the ate (lead poisoning)), platinum-carbon, platinum oxide and like), aryloxy groups (Co aryloxy groups optionally Sub the like can be used. The amount of the catalyst to be used is stituted with at least one lower alkyl group Such as a phenoxy, not particularly restricted providing it does not adversely group, 4-methylphenoxy group, 2-naphthoxy group and the affect the reaction, and preferably, it is 0.001 to 0.1 wt % for like), di-lower alkylamino groups (di-C alkylamino groups the compound represented by the formula (IIX). Such as a dimethylamino group, diethylamino group and the 0903. This reaction can be carried out using a suitable Solvent. Such a solvent is not particularly restricted providing like) or groups represented by the formula: RSO, (wherein, it does not react with a reaction Substrate, reaction reagent and R represents a lower alkyl group or a phenyl optionally product to give a by-product, and those dissolving both the Substituted with at least one lower alkyl group, and r is an reaction Substrate and the reaction reagent are desirable. Used integer of 0, 1 or 2) and the like can be used. as Such a solvent are, for example, aliphatic hydrocarbons 0908. In this reaction, the amount of the compound repre Such as pentane, hexane, heptane, petroleum ether and the sented by the above-mentioned formula (VII) is not particu like, aromatic hydrocarbons such as benzene, toluene, Xylene larly restricted, and may be used in large excess amount as a and the like, esters such as methyl acetate, ethyl acetate, ethyl solvent, and preferably, it is about 0.8 to 5 equivalents for the formate, ethyl propionate and the like, ketones such as compound represented by the formula (IX). acetone, methyl ethyl ketone and the like, ethers such as 0909. A good result may be obtained in some cases by diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, presence of a base or action of a base before or after the tetrahydrofuran, dioxane and the like, nitriles Such as aceto reaction, for the purpose of promoting the reaction and reduc nitrile, propionitrile and the like, acid amides such as dimeth ylformamide, dimethylacetamide and the like, sulfoxides ing by-products. As such a base, there can be used alcoholates Such as dimethyl Sulfoxide and the like, Sulfones such as of alkali metals such as, for example, sodium ethylate, Sulfolane and the like, phosphoric amides such as hexameth Sodium methylate, potassium tert-butoxide and the like; ylphosphoramide and the like, halogenated hydrocarbons organic bases such as, for example, triethylamine, diisopro Such as dichloromethane, chloroform, 1,2-dichloroethane, pylethylamine, pyridine, 4-dimethylaminopyridine, N.N- carbon tetrachloride and the like, aromatic amines such as dimethylaniline and the like; inorganic bases such as, for pyridine, picoline, lutidine, quinoline and the like, and mixed example, potassium carbonate, Sodium carbonate, sodium solvents thereof, water, further, mixed solvents of these com hydroxide, potassium hydroxide, Sodium hydrogen carbon pounds with water. ate, potassium hydrogen carbonate and the like; metal 0904. The reaction temperature is usually about -50 to hydrides Such as, for example, lithium hydride, sodium 200° C., preferably about -30 to 150° C. The reaction time is hydride, potassium hydride and the like; or organic lithium generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, reagents such as, for example, butyllithium, lithiumdiisopro more preferably about 0.1 to 24 hours. pylamide and the like. The amount of the base to be used is not 0905. The resultant compound can be separated and/or particularly restricted providing it does not adversely affect purified by means known perse, for example, concentration, the reaction, and it can also be used in large excess amount for concentration under reduced pressure, liquid nature conver acting as a solvent simultaneously. Sion, transference dissolution, solvent extraction, distillation, 0910. In this reaction, a salt of a compound represented by crystallization, re-crystallization, chromatography and the the formula (VII) and a base, previously prepared, can also be like. used. Alkali metal salts of lithium, Sodium and potassium, and alkaline earth metal salts of magnesium and calcium are Production Method 5 Suitable, among others. The amount of the salt is not particu 0906. The compound (I) can be produced by reacting a larly restricted and the salt may be used in large excess compound represented by the formula (IX): amount, and preferably, it is about 0.8 to 5 equivalents for the compound represented by the formula (IX). 0911. This reaction can be carried out using a suitable (IX) Solvent. Such a solvent is not particularly restricted providing Y it does not react with a reaction Substrate, reaction reagent and product to give a by-product, and those dissolving both the M-CHECH-C=N-Z reaction Substrate and the reaction reagent are desirable. Used as Such a solvent are, for example, aliphatic hydrocarbons (wherein, M represents a leaving group, and other symbols Such as pentane, hexane, heptane, petroleum ether and the are as defined above) with a compound represented by the like, aromatic hydrocarbons such as benzene, toluene, Xylene formula (VII): and the like, esters such as methyl acetate, ethyl acetate, ethyl formate, ethyl propionate and the like, ketones such as X H (VII) acetone, methyl ethyl ketone and the like, ethers such as (symbols in the formula are as defined above). diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, US 2011/0319437 A1 Dec. 29, 2011 42 tetrahydrofuran, dioxane and the like, nitriles Such as aceto organic bases such as, for example, triethylamine, diisopro nitrile, propionitrile and the like, acid amides such as dimeth pylethylamine, pyridine, 4-dimethylaminopyridine, N.N- ylformamide, dimethylacetamide and the like, sulfoxides dimethylaniline and the like; inorganic bases such as, for Such as dimethyl Sulfoxide and the like, Sulfones such as example, potassium carbonate, Sodium carbonate, sodium Sulfolane and the like, phosphoric amides such as hexameth hydroxide, potassium hydroxide, Sodium hydrogen carbon ylphosphoramide and the like, halogenated hydrocarbons ate, potassium hydrogen carbonate and the like; metal Such as dichloromethane, chloroform, 1,2-dichloroethane, hydrides Such as, for example, lithium hydride, sodium carbon tetrachloride and the like, aromatic amines such as hydride, potassium hydride and the like; or organic lithium pyridine, picoline, lutidine, quinoline and the like, and mixed reagents such as, for example, butyllithium, lithiumdiisopro solvents thereof, water, further, mixed solvents of these com pounds with water. pylamide and the like. The amount of the base to be used is not 0912. The reaction temperature is usually about -50 to particularly restricted providing it does not adversely affect 200° C., preferably about -30 to 150° C. The reaction time is the reaction, and it can also be used in large excess amount for generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, acting as a solvent simultaneously. more preferably about 0.1 to 24 hours. 0918. This reaction can be carried out using a suitable 0913. The resultant compound can be separated and/or Solvent. Such a solvent is not particularly restricted providing purified by means known perse, for example, concentration, it does not react with a reaction Substrate, reaction reagent and concentration under reduced pressure, liquid nature conver product to give a by-product, and those dissolving both the Sion, transference dissolution, solvent extraction, distillation, reaction Substrate and the reaction reagent are desirable. Used crystallization, re-crystallization, chromatography and the as Such a solvent are, for example, aliphatic hydrocarbons like, and after separation and/or purification. Such as pentane, hexane, heptane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, Xylene Production Method 6 and the like, esters such as methyl acetate, ethyl acetate, ethyl 0914. The compound (I) can be produced by reacting a formate, ethyl propionate and the like, ketones such as acetone, methyl ethyl ketone and the like, ethers such as compound represented by the formula (X): diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane and the like, nitriles Such as aceto (X) nitrile, propionitrile and the like, acid amides such as dimeth S ylformamide, dimethylacetamide and the like, sulfoxides H Such as dimethyl Sulfoxide and the like, Sulfones such as X-CHCH-C-N-Z Sulfolane and the like, phosphoric amides such as hexameth ylphosphoramide and the like, halogenated hydrocarbons (wherein, symbols are as defined above) with a compound Such as dichloromethane, chloroform, 1,2-dichloroethane, represented by the formula (X): carbon tetrachloride and the like, aromatic amines such as pyridine, picoline, lutidine, quinoline and the like, and mixed solvents thereof, water, further, mixed solvents of these com (wherein, Y' represents an alkyl group optionally substi pounds with water. tuted, alkenyl group optionally Substituted or alkynyl group 0919. The reaction temperature is usually about -50 to optionally substituted, M represents a leaving group and 200° C., preferably about -30 to 150° C. The reaction time is other symbols are as defined above). generally about 0.11 to 96 hours, preferably 0.1 to 72 hours, 0915. As the leaving group represented by M, for more preferably about 0.1 to 24 hours. example, halogens, acyloxy groups (Co acyloxy groups 0920. The resultant compound can be separated and/or such as C. alkylcarbonyloxy groups optionally substituted purified by means known perse, for example, pulverization, with 1 to 3 halogen (s) such as a formyloxy group, acetoxy concentration, concentration under reduced pressure, liquid group, propionyloxy group, trifluoroacetoxy group and the nature conversion, transference dissolution, solvent extrac like; Cz-o-benzoyloxy groups optionally substituted with at tion, distillation, crystallization, re-deposition, re-crystalliza least one alkyl group Such as a benzoyloxy group, 4-methyl tion, chromatography, high performance liquid chromatogra benzoyloxy group and the like; C alkoxycarbonyloxy phy (HPLC), demineralized resin column chromatography groups such as methoxycarbonyloxy, t-butoxycarbonyloxy and the like. and the like) or groups represented by the formula: RSO, (wherein, R represents a lower alkyl group or a phenyl Production Method 7 optionally substituted with at least one lower alkyl group, and r is an integer of 0, 1 or 2) and the like can be used. 0921. The compound (I) can be produced by reacting a 0916. In this reaction, the amount of the compound repre compound represented by the formula (XII): sented by the above-mentioned formula (XI) is not particu larly restricted, and may be used in large excess amount as a solvent, and preferably, it is about 0.8 to 5 equivalents for the (XII) compound represented by the formula (X). | H 0917. A good result may be obtained in some cases by X-CHECH-C-N-Z presence of a base or action of a base before or after the reaction, for the purpose of promoting the reaction and reduc ing by-products. As such a base, there can be used alcoholates (wherein, symbols are as defined above) with a compound of alkali metals such as, for example, sodium ethylate, represented by the formula (XIII): Sodium methylate, potassium tert-butoxide and the like; (Y2).O.BF (XIII) US 2011/0319437 A1 Dec. 29, 2011

(wherein, Y' represents an alkyl group optionally substi tuted, alkenyl group optionally Substituted or alkynyl group optionally substituted). (XIV) 0922. In this reaction, the amount of the compound repre O H sented by the above-mentioned formula (XIII) is not particu X-CHECH-C-N-Z larly restricted, and may be used in large excess amount as a solvent, and preferably, it is about 0.8 to 5 equivalents for the with a halogenating agent. compound represented by the formula (XII). 0930. As the halogenating agent which can be used in this 0923. This reaction can be carried out using a suitable reaction, thionyl chloride, Sulfuryl chloride, phosphorus oxy Solvent. Such a solvent is not particularly restricted providing chloride, phosphorus pentachloride, carbon tetrachloride, it does not react with a reaction Substrate, reaction reagent and carbon tetrabromide and the like are mentioned. product to give a by-product, and those dissolving both the 0931. In this reaction, the amount of the above-mentioned reaction Substrate and the reaction reagent are desirable. Used halogenating reagent is not particularly restricted, and may be as Such a solvent are, for example, aliphatic hydrocarbons used in large excess amount as a solvent, and preferably, it is Such as pentane, hexane, heptane, petroleum ether and the about 0.8 to 5 equivalents for the compound represented by like, aromatic hydrocarbons such as benzene, toluene, Xylene the formula (XIV). and the like, esters such as methyl acetate, ethyl acetate, ethyl 0932. A good result may be obtained in some cases by formate, ethyl propionate and the like, ketones such as presence of a base or action of a base before or after the acetone, methyl ethyl ketone and the like, ethers such as reaction, for the purpose of promoting the reaction and reduc diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, ing by-products. As such a base, there can be used organic tetrahydrofuran, dioxane and the like, nitriles Such as aceto bases such as, for example, triethylamine, diisopropylethy nitrile, propionitrile and the like, acid amides such as dimeth lamine, pyridine, 4-dimethylaminopyridine, N,N-dimethyla ylformamide, dimethylacetamide and the like, sulfoxides niline and the like; metal hydrides such as, for example, Such as dimethyl Sulfoxide and the like, Sulfones such as lithium hydride, sodium hydride, potassium hydride and the Sulfolane and the like, phosphoric amides such as hexameth like; organic lithium reagents such as, for example, butyl ylphosphoramide and the like, halogenated hydrocarbons lithium, lithium diisopropylamide and the like; orphosphorus Such as dichloromethane, chloroform, 1,2-dichloroethane, compounds Such as, for example, triphenylphosphine and the carbon tetrachloride and the like, and mixed solvents thereof. like. The amount of the base to be used is not particularly 0924. The reaction temperature is usually about -50 to restricted providing it does not adversely affect the reaction, 200° C., preferably about -30 to 150° C. The reaction time is and it can also be used in large excess amount for acting as a generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, Solvent simultaneously. more preferably about 0.1 to 24 hours. 0933. This reaction can be carried out using a suitable 0925. The resultant compound can be separated and/or Solvent. Such a solvent is not particularly restricted providing purified by means known perse, for example, pulverization, it does not react with a reaction Substrate, reaction reagent and concentration, concentration under reduced pressure, liquid product to give a by-product, and those dissolving both the nature conversion, transference dissolution, solvent extrac reaction Substrate and the reaction reagent are desirable. Used tion, distillation, crystallization, re-deposition, re-crystalliza as Such a solvent are, for example, aliphatic hydrocarbons tion, chromatography, high performance liquid chromatogra Such as pentane, hexane, heptane, petroleum ether and the phy (HPLC), demineralized resin column chromatography like, aromatic hydrocarbons such as benzene, toluene, Xylene and the like. and the like, esters such as methyl acetate, ethyl acetate, ethyl 0926 The compound produced by the above-mentioned formate, ethyl propionate and the like, ketones such as production methods can also be further subjected to methods acetone, methyl ethyl ketone and the like, ethers such as known perse, for example, alkylation, alkenylation, alkyny diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, lation, acylation, amination, Sulfidation, Sulfinylation, Sul tetrahydrofuran, dioxane and the like, nitriles Such as aceto fonation, oxidation, reduction, halogenation, nitration, cross nitrile, propionitrile and the like, acid amides such as dimeth coupling reaction and the like to convert its substituent into ylformamide, dimethylacetamide and the like, sulfoxides other desired substituent. Such as dimethyl Sulfoxide and the like, Sulfones such as 0927. The compound obtained by the above-mentioned Sulfolane and the like, phosphoric amides such as hexameth production methods can be separated and/orpurified by con ylphosphoramide and the like, halogenated hydrocarbons ventional methods, for example, pulverization, concentra Such as dichloromethane, chloroform, 1,2-dichloroethane, tion, concentration under reduced pressure, liquid nature con carbon tetrachloride and the like, aromatic amines such as version, transference dissolution, solvent extraction, pyridine, picoline, lutidine, quinoline and the like, and mixed distillation, crystallization, re-deposition, re-crystallization, solvents thereof. chromatography, high performance liquid chromatography 0934. The reaction temperature is usually about -50 to (HPLC), demineralized resin column chromatography and 200° C., preferably about -30 to 150° C. The reaction time is the like. generally about 0.1 to 96 hours, preferably 0.1 to 72 hours, more preferably about 0.1 to 24 hours. Reference Production Method 0935 The resultant compound can be separated and/or purified by means known perse, for example, filtration, pull 0928. A method for producing a compound to be used for Verization, concentration, concentration under reduced pres production of the compound (I) will be described below. Sure, transference dissolution, Solvent extraction, distillation, 0929. A compound (1I) wherein M' represents a halogen crystallization, re-deposition, re-crystallization and the like, atom can be obtained by reacting a compound represented by and after separation and/or purification, alternatively as the the formula (XIV): reaction mixture itself, may be used as a raw material for the US 2011/0319437 A1 Dec. 29, 2011 44

Subsequent reaction. The compound as a starting Substance in acid, oxalic acid, Succinic acid, benzoic acid, p-toluene this reaction is a known compound or can be produce by Sulfonic acid, methanesulfonic acid and trifluoroacetic acid, known methods (Chem. Pharm. Bull. 48, P1854, 2000, and and the like. the like). 0946 Each of the compounds (I) may contain steric iso 0936. The compound represented by the formula (III) mers such as optical isomers based on one or more asymmet belongs to, for example, thiols, alcohols, phenols, primary or ric carbon atom(s) and geometric isomers based on one or more double bond(s), and the like. Such isomers and mixtures secondary amines, and these are known compounds or can be thereof are also entirely included in the range of the present produced by known methods. invention. 0937. The compound represented by the formula (VI) is a 0947 The compounds (I) can include isomers such as known compound or can be produced by known methods tautomers, geometric isomers, steric isomers and the like, and (Chem. Lett. P1261, 1989, Chem. Berichte 109, P1643, 1976, in the present invention, these isomers and mixtures thereof and the like). are all included in the formula (I). 0938. The compound represented by the formula (VII) 0948. Some of the compounds (I) are in the form of solvate belongs to, for example, thiols, alcohols, phenols, primary or (for example, hydrate and the like), and these forms are also secondary amines, and these are known compounds or can be included in the range of the present invention. produced by known methods. 0949. Some of the compounds (I) are in the form of crystal 0939. The compound represented by the formula (IIX) is a and/or amorphous Substance, and these forms are also known compound or can be produced by known methods included in the range of the present invention. (Chem. Lett. P1261, 1989, and the like). 0950 In the present invention, some of the compounds are 0940. The compounds to be produced by the above-men in the form of pro-drug, and these forms are also included in tioned Production Methods 1 to 7 and Reference Production the range of the present invention. Method can also be further subjected to methods known per 0951. The compound (I) is effective for controlling a se, for example, alkylation, alkenylation, alkynylation, aryla hygiene pest and an animal and plant parasitic pest, and tion, hetero arylation, acylation, amination, Sulfidation, Sulfi exhibits a strong insecticidal activity by treating an animal nylation, Sulfonation, oxidation, reduction, halogenation, and a plant which are parasitized by a pest. In addition, the nitration and the like to convert its substituent into other compound (I) have little phytotoxic effects on a plant, and desired substituent. have little toxicity to fishes and, thus, have both safe and 0941 The compounds to be obtained by the above-men advantageous nature as an agent for controlling pests for tioned Production Methods 1 to 7 and Reference Production hygiene, the livestock industry, pets, horticulture and agricul Method can be separated and/or purified by conventional ture. methods, for example, pulverization, concentration, concen 0952. When the compound (I) is used as a pesticide, in tration under reduced pressure, liquid nature conversion, particular, as an insecticide, the compound is used in a form transference dissolution, solvent extraction, distillation, crys which general pesticides and Veterinary drugs can take, that tallization, re-deposition, re-crystallization, chromatography, is, a dosage form Such as an emulsion, a solution, a micro high performance liquid chromatography (HPLC), deminer emulsion, a flowable formulation, an oil solution, a wettable powder, a powder, a granule, a fine granule, a seed coating alized resin column chromatography and the like. agent, a Smoking agent, a tablet, a microcapsule, a spray 0942. The compounds to be obtained by the above-men formulation, an aerosol, a carbon dioxide formulation, a heat tioned Production Methods 1 to 7 and Reference Production fumigate formulation Such as mosquito coil, electric mos Method can also be obtained in the form of hydrate, and quito tablet and electric insecticidal Solution, an EW agent, an hydrates thereofare also included in the range of the present ointment, a poison bait, a capsule, a pellet, an injectable, a invention. resinous formulation, a shampoo preparation and the like, by 0943 Regarding the compound (I), an acidic group Such dissolving or dispersing one kind or two kinds or more (pref as a Sulfonyl group, carboxyl group in a Substituent in the erably, one kind or more, and not more than three kinds) of the molecule can forman pesticidally acceptable base salt of an compound (I) or a salt thereof as an active ingredient in a inorganic base, organic base and the like, and a basic group Suitable liquid carrier, or mixing with or being adsorbed on a Such as a basic nitrogenatom in the molecule, an amino group Suitable solid carrier depending on a use purpose. To these in the Substituent, and the like can form an pesticidally preparations, if needed, an emulsifying agent, a Suspending acceptable acid-addition salt of an inorganic acid, organic agent, a developer, a penetrant, a wetting agent, a thickener, a acid and the like. stabilizer or the like may be added, and they can be prepared 0944. The inorganic base salts include, for example, salts by a method known perse. Namely, the pesticidal composi of alkali metals (sodium, potassium and the like), alkaline tion of the present invention comprises the compound (I) or a earth metals (calcium and the like) and ammonia, and the salt thereof as an active ingredient and an inert carrier. organic base salts include, for example, salts with dimethy 0953. As a liquid carrier (solvent) to be used, for example, lamine, triethylamine, N,N-dimethylaniline, piperazine, pyr Solvents such as water, alcohols (e.g. methyl alcohol, ethyl rolidine, piperidine, pyridine, 2-phenylethylamine, benzy alcohol, n-propyl alcohol, isopropyl alcohol, benzyl alcohol, lamine, ethanolamine, diethanolamine, 1,8-diazabicyclo5.4. ethylene glycol etc.), ketones (e.g. acetone, methyl ethyl Oundecene (hereinafter, abbreviated as DBU), and the like. ketone, methyl isobutyl ketone, cyclohexanone etc.), ethers 0945. The inorganic acid-addition salts include, for (e.g. tetrahydrofuran, ethylene glycol monomethyl ether, example, salts with hydrochloric acid, hydrobromic acid, diethylene glycol monomethyl ether, diethylene glycol mono hydroiodic acid, Sulfuric acid, nitric acid, phosphoric acid and ethyl ether, propylene glycol monomethyl ether etc.), ali perchloric acid, and the organic acid-addition salts include, phatic hydrocarbons (e.g. kerosine, kerosene, fuel oil, for example, salts with formic acid, acetic acid, propionic machine oil etc.), aromatic hydrocarbons (e.g. toluene, US 2011/0319437 A1 Dec. 29, 2011

Xylene, Solvent naphtha, methylnaphthalene etc.), haloge priately used by mixing one kind or two kinds at a Suitable nated hydrocarbons (e.g. dichloromethane, chloroform, car ratio. In addition, the compound (I) can also be used appro bon tetrachloride etc.), acid amides (e.g. N,N-dimethylfor priately by compounding with, for example, other insecticide mamide, N,N-dimethylacetamide, N-methylpyrrolidone (pyrethroid insecticide, organic phosphorus insecticide, car etc.), esters (e.g. ethyl acetate, butyl acetate, fatty acid glyc bamate insecticide, neonicotinoid insecticide, natural insec erinester, Y-butyrolactone etc.), nitriles (e.g. acetonitrile, pro ticide etc.), an acaricide, a machine oil, a nematocide, a her pionitrile etc.), carbonates (e.g. propylene carbonate etc.), bicide, a plant hormone agent, a plant growth regulating Vegetable oils (e.g. rapeseed oil, cotton seed oil etc.), and the Substance, an fungicidal agent (e.g. copper fungicidal agent, like are suitable. These can be appropriately used by mixing organic chlorine fungicidal agent, organic sulfur fungicidal one kind or two kinds or more (preferably one kind or more, agent, phenol fungicidal agent etc.), a Synergist, an attractant, and not more than three kinds) at a suitable ratio. a repellent, a drug harm alleviating agent, a pigment, a fertil 0954. As a solid carrier (diluent, bulking agent), a veg izer, an animal feed (feed for livestock Such as cow, pig and etable powder (e.g. soybean powder, tobacco powder, wheat hence chicken, feed for pet animal such as dog and cat, feed powder, wood meal etc.), a mineral powder (e.g. clays such as for raised fish Such as young yellowtail and sea bream), Vet kaolin, bentonite, acid clay etc., talcs such as talc powder, erinary medicaments (medicaments for treating or preventing agalmatolite powder etc., silicas such as diatomaceous earth, diseases of livestock, pet animal, raised fish), a veterinary mica powder etc.), alumina, a Sulfur powder, an active carbon, nutrient and the like. calcium carbonate, potassium chloride, ammonium Sulfate, 0958. The ratio of the compound (I) contained in the pes Sodium hydrogen carbonate, lactose, urea and the like are ticidal composition of the present invention is usually about used, and these can be appropriately used by mixing one kind 0.1 to 80% by weight, preferably about 1 to 20% by weight or two kinds or more (preferably one kind or more, and not relative to the total amount of the composition. Specifically, more than three kinds) at a suitable ratio. when the compound is used as an emulsion, a solution or a 0955. As a gaseous carrier, for example, fluorocarbon, wettable powder (e.g. granular wettable powder), usually butane gas, LPG (liquid petroleum gas), dimethyl ether, car about 1 to 80% by weight, preferably about 1 to 20% by bon dioxide and the like is used and these can be appropriately weight is suitable. When used as an oil solution or a powder, used by mixing one kind or two kinds at a Suitable ratio. usually about 0.1 to 50% by weight, preferably about 0.1 to 0956. In addition, as an ointment base materials, for 20% by weight is suitable. When used in a granule, usually example, one kind or two kinds or more (preferably, one kind about 1 to 50% by weight, preferably about 1 to 20% by or more, and not more than three kinds) of materials selected weight is suitable. from the group consisting of polyethylene glycol, pectin, 0959) Other pesticidaly active ingredient (e.g. an insecti polyhydric alcohol ester of higher fatty acid Such as cide, a herbicide, an acaricide and/or a fungicide) which is monostearic acid glycerinester and the like, cellulose deriva compounded in the pesticidal composition of the present tive Such as methylcellulose and the like, sodium alginate, invention is used usually in the range of about 0.1 to 80% by bentonite, higher alcohol, polyhydric alcohol Such as glycerin weight, preferably about 1 to 20% by weight relative to the and the like, Vaseline, white Vaseline, liquid paraffin, lard, total amount of the preparation. various vegetable oils, lanolin, dehydrated lanolin, hardened 0960. The content of an additive other than the aforemen oil, resins and the like, or these materials wherein following tioned active ingredients differs depending on a kind or a various Surfactants are added thereto are appropriately used. content of an active ingredient or a dosage form of a prepa 0957. As a surfactant used as an emulsifying agent, a ration, and is usually about 0.001 to 99.9% by weight, pref developer, a penetrant, a dispersant and the like, depending on erably about 1 to 99% by weight. More specifically, it is the necessity, nonionic and anionic Surfactants such as Soaps, preferable to add a surfactant at usually about 1 to 20% by polyoxyethylene alkylaryl ethers e.g. Neugen (trade name), weight, more preferably about 1 to 15% by weight, a flowing EA142 (trade name); manufactured by Dai-ichi Kogyo Seiy aid at about 1 to 20% by weight, and a carrier at about 1 to aku Co., Ltd., Nonal (trade name); manufactured by Toho 90% by weight, preferably at about 1 to 70% by weight Chemical Industries Co., Ltd., alkyl Sulfate salts e.g. Emar relative to the total amount of the composition. Specifically, 10 (trade name), Emar 40 (trade name); manufactured by Kao when a solution is prepared, it is preferable to add a surfactant Corporation, alkylbenzene Sulfonic acid salts e.g. Neogen at usually about 1 to 20% by weight, preferably 1 to 10% by (trade name), Neogen T(trade name); manufactured by Dai weight, and water at about 20 to 90% by weight. An emulsion ichi Kogyo Seiyaku Co., Ltd., Neoperex: manufactured by or a wettable powder (e.g. granular wettable powder) should Kao Corporation, polyethylene alkylethers e.g., Neugen be diluted with water appropriately (e.g. about 100 to 5.000 ET-135 (trade name); manufactured by Dai-ichi Kogyo Seiy fold) for use to spray. aku Co., Ltd., polyoxyethylene polyoxypropylene block 0961 Typical examples of fungicidal agent, plant hor copolymers e.g., Nonipol PE-64 (trade name); manufactured mone agent, plant growth regulating Substance, herbicide, by Sanyo Chemical Industries, Ltd., polyhydric alcohol and pesticide Such as insecticide, acaricide and nematocide esters e.g. Tween 20 (trade name), Tween 80 (trade name); and the like (including isomers and salts thereof) which can manufactured by Kao Corporation, alkylsulfo Succinic acid be used by mixing with the compound (I) or salts thereof of salts e.g. Sanmolin OT20 (trade name); manufactured by the present invention are shown below. Sanyo Chemical Industries, Ltd., Newcalgen EX70 (trade 0962 (1) Organic Phosphorous Compounds name); manufactured by Takemoto Oil & Fat Co., Ltd., 0963 Acephate, Aluminium phosphide, butathiofos, alkylnaphthalene sulfonic acid salts e.g. Newcalgen WG-1 cadusafos, chlorethoxyfos, chlorfenVinphos, chlorpyrifos, (trade name); manufactured by Takemoto Oil & Fat Co., chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP Ltd., alkenyl sulfonic acid salts e.g. Solpol 5115 (trade (dichlorodiisopropyl ether), dichlofenthion (ECP), dichlor name); manufactured by Toho Chemical Industries Co., Ltd. Vos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, and the like are appropriately used and these can be appro ethion, ethoprophos, etrimfos, fenthion (MPP), fenitrothion US 2011/0319437 A1 Dec. 29, 2011 46

(MEP), fosthiazate, formothion, Hydrogen phosphide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, isofenphos, isoxathion, malathion, mesulfenfos, methi formetanate, metam-ammonium, metam-Sodium, Methyl dathion (DMTP), monocrotophos, naled (BRP), oxydeprofos bromide, nidinotefuran, Potassium oleate, protrifenbute, (ESP), parathion, phosalone, phosmet (PMP), pirimiphos spiromesifen, Sulfur, metaflumizone, spirotetramat, pyriflu methyl, pyridafenthion, quinallphos, phenthoate (PAP), pro quinazon, Chlorantraniliprole, a compound represented by fenofos, propaphos, prothiofos, pyraclorfos, salithion, Sul formula (A) profos, tebupirimfos, temephos, tetrachlorvinphos, terbufos. thiometon, trichlorphon (DEP), vamidothion and the like: 0964 (2) Carbamate Compounds (A) 0965 Alanycarb, bendiocarb, benfuracarb, BPMC, car R2 baryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isopro O W \ carb (MIPC), metolcarb, methomyl, methiocarb, NAC, R1 N 1. oxamyl, pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb and the like: R6 NH R3 0966 (3) Synthetic pyrethroid compounds N21 0967 Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyper NC S methrin, deltamethrin, esfenvalerate, ethofenproX, fenpro O pathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, N R7 fluvalinate, halfenproX, imiprothrin, permethrin, prallethrin, R41NRs pyrethrins, resmethrin, sigma-cypermethrin, Silafluofen, tefluthrin, tralomethrin, transfluthrin, 2,3,5,6-tetrafluoro-4- wherein, R' represents a methyl group, a chlorine atom, a (methoxymethyl)benzyl (EZ)-(1RS,3RS;1RS,3SR)-2,2- bromine atom or a fluorine atom, R represents a fluorine dimethyl-3-prop-1-enylcyclopropa necarboxylate, 2,3,5,6- atom, a chlorine atom, a bromine atom, C1-4 haloalkyl group tetrafluoro-4-methylbenzyl (EZ)-(1RS,3RS;1RS,3SR)-2.2- or C1-4 haloalkoxy group, R represents a fluorine atom, a dimethyl-3-prop-1-enylcyclopropa necarboxylate, 2,3,5,6- chlorine atom or a bromine atom, R represents a hydrogen tetrafluoro-4-(methoxymethyl)benzyl (1RS,3RS;1RS,3SR)- atom; Ca alkyl group optionally substituted with a methoxy 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclo group, one or more of halogen atom(s), a cyano group, a propanecarboxylate and the like; methylthio group, a methylsulfinyl group or a methylsulfonyl 0968 (4) Nereistoxin Compounds group: C. alkenyl: Csa alkynyl; or Css cycloalkyl, R rep 0969 Cartap, bensultap, thiocyclam, monosultap, bisul resents a hydrogen atom or a methyl group, R represents a tap and the like; hydrogen atom, a fluorine atom or a chlorine atom, R7 repre 0970 (5) Neonicotinoid Compounds sents a hydrogenatom, a fluorine atom or a chlorine atom and 0971 Imidacloprid, nitenpyram, acetamiprid, thia the like. methoxam, thiacloprid, dinotefuran, clothianidin and the 0986 Acaricides (Active ingredients for acaricide) like: include, for example, acequinocyl, amitraz, benzoximate, 0972 (6) Benzoylurea Compounds bifenazate, bromopropylate, chinomethionat, chlorobenzi 0973 ChlorfluaZuron, bistrifluoron, diafenthiuron, late, CPCBS (chlorfenson), clofentezine, cyflumetofen, diflubenzuron, fluaZuron, flucycloxuron, flufenoxuron, kelthane (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, hexaflumuron, lufenuron, novaluron, noviflumuron, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, pro teflubenzuron, triflumuron and the like; pargite (BPPS), polynactins, pyridaben, Pyrimidifen, 0974 (7) Phenylpyrazole Compounds tebufenpyrad, tetradifon, spirodiclofen, amidoflumet and the 0975 Acetoprole, ethiprole, fipronil, vaniliprole, like. pyriprole, pyrafluprole and the like; 0987 Nematocides (Active ingredients of nematocide) 0976 (8) Bt Toxins include, for example, DCIP, fosthiazate, levamisol, methyl 0977 Live spores and produced crystal toxin derived from Sothiocyanate, morantel tartarate and the like. bacillus thuringiensis, and a mixture thereof; 0988 Fungicides include, for example, acibenzolar-S-me 0978 (9) Hydrazine Compounds thyl, amobam, ampropylfos, anilazine, azoxystrobin, benal 0979 Chromafenozide, halofenozide, methoxyfenozide, axyl, benodanil, benomyl, benthiavalicarb, benthiazole, tebufenozide and the like; bethoxazin, bitertanol, blasticidin-S, Bordeaux mixture, bos 0980 (10) Organic Chlorine Compounds calid, bromuconazole, buthiobate, Calcium hypochlorite, 0981 Aldrin, dieldrin, dienochlor, endosulfan, methoxy Calcium polysulfide, captan, carbendazol, carboxin, carpro chlor and the like: pamid, chlobenthiaZone, chloroneb, chloropicrin, chlorotha 0982 (11) Natural Insecticides lonil (TPN), chlorthiophos, Cinnamaldehyde, clozylacon, 0983. Machine oil, nicotine-sulfate and the like: CNA (2,6-Dichloro-4-nitroaniline), Copper hydroxide, Cop 0984 (12) Other Insecticides per Sulfate, cyaZofamid, cyfluphenamid, cymoxanil, cypro 0985 Avermectin-B, bromopropylate, buprofezin, chlor conazole, cyprodinil, cyprofuram, dazomet, debacarb, phenapyr. cyromazine, D-D (1,3-Dichloropropene), ema dichlofluanid, D-D (1,3-Dichloropropene), diclocymet, mectin-benzoate, fenaZaquin, flupyrazofos, hydroprene, diclomezine, diethofencarb, difenoconazole, diflumetorim, indoxacarb, metoxadiaZone, milbemycin-A, pymetrozine, dimefluazole, dimethirimol, dimethomorph, diniconazole pyridalyl pyriproxyfen, spinosad, Sulfluramid, tolfenpyrad, M. dinocap, edifenphos, epoxiconazole, nickel dimeth triazamate, flubendiamide, SI-0009, cyflumetofen, Arsenic yldithiocarbamate, etaconazole, ethaboxam, ethirimol, acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, etridiazole, famoxadone, fenamidone, fenarimol, fenbucona US 2011/0319437 A1 Dec. 29, 2011 47

Zole, FendaZoSulam, fenhexamid, fenoxanil, fenpiclonil, fen Indole acetic acid (IAA), Indole butyric acid, iodosulfuron, propidin, fenpropimorph, fentiazon, fentin hydroxide, ferim ioxynil-octanoate, isouron, isoxachlortole, isoxadifen, kar Zone, fluaZinam, fludioxonil, flumetover, flumorph, butilate, lactofen, lenacil, linuron, LGC-42153, Maleic fluoroimide, fluotrimazole, fluoxastrobin, fluguinconazole, hydrazide, mecoprop (MCPP), 2-Methyl-4-chlorophenoxy flusilazole, flusulfamide, flutolanil, flutriafol, fosetyl-Al. acetic acid salts, MCPA-thioethyl, 2-Methyl-4-chlorophe fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, fur noxybutanoic acidethyl ester, mefenacet, mefluidide, mepi quat, mesosulfuron, mesotrione, methyl daimuron, conazole-cis, hexaconazole, hymexaZol, IBP imazalil, imi metamifop, metolachlor, metribuzin, metSulfuron-methyl, benconazole, iminoctadine-albesilate, iminoctadine-triac molinate, naphthylacetic acid, 1-naphthaleneacetamide, etate, iodocarb, ipconazole, iprodione, iprovalicarb, naproanilide, napropamide, n-decyl alcohol, nicosulfuron, isoprothiolane, kasugamycin, kresoxim-methyl, mancoZeb, n-phenylphthalamic acid, orbencarb, oxadiazon, oxaziclom maneb, mepanipyrim, mepronil, metalaxyl, metalaxyl-M, efone, oxine-Sulfate, paclobutraZol, paraquat, Pelargonic metam-Sodium, methasulfocarb. Methyl bromide, metcona acid, pendimethalin, penoXSulam, pentoxazone, pethoxam Zole, methfuroxam, metominostrobin, metrafenone, metSul ide, phenmedipham, picloram, picolinafen, piperonylbutox foVax, mildiomycin, milineb, myclobutanil, mycloZolin, ide, piperophos, pretilachlor, primisulfuron-methyl, procar nabam, orysastrobin, ofurace, oxadixyl, oxolinic acid, oxpo baZone, prodiamine, profluaZol, profoxydim, prohexadione conazole, oxycarboxin, oxytetracycline, pefurazoate, pen calcium, prohydrojasmon, prometryn, propanil, conazole, pencycuron, picoxystrobin, polycarbamate, poly propoxycarbazone, propyZamide, pyraclonil, pyraflufen oxin, Potassium hydrogen carbonate, probenazole, ethyl, pyrazolate, pyrazosulfuron-ethyl, pyrazoxyfen, prochloraz, procymidone, propamocarb-hydrochloride, pyribenZoxim, pyributicarb, pyridafol, pyridate, pyriftalid, propiconaole, propineb, produinazid, prothiocarb, prothio pyriminobac-methyl, pyrithiobac, quiclorac, quinoclamine, conazole, pyracarbolid, pyraclostrobin, pyrazophos, pyribu quizalofop-ethyl, rimsulfuron, Sethoxydim, Siduron, ticarb, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, simazine, simetryn, Sodium chlorate, Sulfosulfuron, Swep quintoZene (PCNB), silthiopham, Simeconazole, Sipcona (MCC), tebuthiuron, tepraloxydim, terbacil, terbucarb Zole, Sodium bibarbonate, sodium hypochlorite, (MBPMC), thenylchlor, thiazafluoron, thidiaZuron, thifen spiroxamine, ((E)-22-(2,5-dimethylphenoxymethyl)phe sulfuron-methyl, triaziflam, tribufos, triclopyr, tridiphane, nyl-2-m ethoxyimino-N-methylacetamide), Streptomycin, trifloxysulfuron, trifluralin, trinexapac-ethyl, tritosulfuron, uniconazole-P and Vemolate (PPTC). Sulfur, tebuconazole, tecloftalam, tetraconazole, thiabenda 0990. The pesticidal composition of the present invention Zole, thiadinil, thiram (TMTD), thifluzamide, thiophanate can also be used further in admixture with a synergist Such as methyl, tolclofos-methyl, TPN, triadimefon, triadimenol, piperonylbutoxide, sesamex, sulfoxide, N-(2-ethylhexyl)-8, triaZOxide, triclamide, tricyclazole, tridemorph, triflumizole, 9,10-trinorborn-5-en-2,3-dicarboxylmide (MGK264), N-de trifloxystrobin, triforine, triticonazole, validamycin, Vinclo cylimidazole, WARF-antiresistant TBPT, TPP, IBP, PSCP, Zolin, Viniconazole, Zineb, Ziram and Zoxamide. Iodomethane (CH, I), t-phenylbutenone, diethylmaleate, 0989 Active ingredients of the herbicides, plant hormone DMC, FDMC, ETP, ETN and the like, and furthermore, may agent and plant growth regulators include, for example, be used in admixture with a safener Such as benoxacor, clo Abscisic acid, acetochlor, acifluorfen-Sodium, alachlor, quintocet-mexyl, cyometrinil, daimuron, dichlormid, alloxydim, ametryn, amicarbazone, amidosulfuron, aminoet fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furila hoxyvinylglycine, aminopyralid, AC94, 377, amiprofoS-me Zole, mefenpyr-diethyl, MG191, naphthalic anhydride and thyl, ancymidol, asulam, atrazine, aviglycine, azimsulfuron, oxabetrinil. beflubutamid, benfluralin, benfuresate, bensulfuron-methyl, bensulide (SAP), bentazone, benthiocarb, benzamizole, ben 0991. Furthermore, the compound (I) or salts thereof of Zfendizone, benzobicyclon, benzofenap, benzyl adenine, the present invention may be used by mixture with a control benzylaminopurine, bialaphos, bifenox, Brassinolide, bro ling agent for an outside-parasitic arthropod such as IGR macil, bromobutide, butachlor, butafenacil, butamifos, buty agents (juvenile hormone-like Substances such as methop late, cafenstrole, Calcium carbonate, Calcium peroxide, car rene, fenoxycarb and the like, chitinsynthaseinhibitorSSu baryl, chlomethoxynil, chloridazon, chlorimuron-ethyl, chaslufenuron, flufenoXuron, novaluron, hexaflumuron, chlorphthalim, chlorpropham, chlorsulfuron, chlorthal-dim teflubenzuron, diflubenzuron, triflumuron and the like, insect ethyl, chlorthiamid (DCBN), choline chloride, cinidon-ethyl, growth regulating agents such as cyromazine, pyriproxyfen cinmethylin, cinosulfuron, clethodim, clomeprop, cloxy and the like), and neonicotinoid compounds (nitenpyram fonac-sodium, chlormeduat chloride, 4-CPA (4-chlorophe etc.), or may be used by mixture with a controlling agent for noxyacetic acid), cliprop, clofencet, cumyluron, cyanazine, inner parasite Such as an above-mentioned IGR agent as in cyclanilide, cycloSulfamron, cyhalofop-butyl, 2,4-Dichlo Vivo administration agent for animal, a controlling agent for rophenoxyacetic acid salts, dichlorprop (2,4-DP), daimuron, filaria (macrollide compounds such as Selamectin, ivermectin, dalapon (DPA), dimethenamid-P daminozide, dazomet, milbemycin, moxidectin etc.) or the like, and further may be n-Decyl alcohol, dicamba-sodium (MDBA), dichlobenil used by mixture with an antibacterial agent for animal, vac (DBN), cine, therapeutic agent, nutritional Supplement and bait. diflufenican, dikegulac, dimepiperate, dimethametryn, 0992 Examples of the pest against which the compound dimethenamid, diguat, dithiopyr, diuron, endothal, epoc (I) or a salt thereofhas an activity include noxious arthropods holeone, esprocarb, ethephon, ethidimuron, ethoxysulfuron, Such as insect pests, acarine pests and the like, and nematode ethychloZate, etobenzanid, fenarimol, fenoxaprop-ethyl, fen pests. Specific examples are listed below: traZamide, flazasulfuron, florasulam, fluaZifop-butyl, flua 0993 Hemiptera:- Zolate, flucarbazone, flufenacet, flufenpyr, flumetralin, flumi 0994 Planthoppers (Delphacidae) such as small brown oxazin, flupropanate-sodium, flupyrsulfuron-methyl planthopper (Laodelphax striatellus), brown rice planthopper sodium, flurprimidol, fluthiacet-methyl, foramsulfuron, (Nilaparvata lugens), and white-backed rice planthopper forchlorfenuron, formesafen, gibberellin, glufosinate, gly (Sogatella fircifera); leafhoppers (Deltocephalidae) Such as phosate, halosulfuron-methyl, hexaZinone, imaZamox, green rice leafhopper (Nephotettix cincticeps), and green rice imazapic, imazapyr, imazaquin, imaZoSulfuron, inabenfide, leafhopper (Nephotettix virescens); aphids (Aphididae) Such US 2011/0319437 A1 Dec. 29, 2011 48 as cotton aphid (Aphis gossypii), green peach aphid (Myzus (Oulema Oryzae), rice curculio (Echinocnemus squameus), persicae), cabbage aphid (Brevicoryne brassicae), pota rice water weevil (Lissorhoptrus Oryzophilus), Anthonomus toaphid (Macrosiphum euphorbiae), foxglove aphid (Aula grandis, azuki bean weevil (Callosobruchus chinensis), Sphe corthum Solani), oat bird-cherryaphid (Rhopalosiphun nophorus venatus, Japanese beetle (Popillia japonica), padi), and tropical citrus aphid (Toxoptera citricidus); Stink cupreous chafer (Anomala cuprea), corn root worm (Di bugs (Pentatomidae) Such as green Stink bug (Nezara anten abrotica spp.), Colorado beetle (Leptinotarsa decemlineata), nata), bean bug (Riptortus clavetus), rice bug (Leptocorisa click beetle (Agriotes spp.), cigarette beetle (Lasiodermaser chinensis), white spotted spined bug (Eysarcoris parvus), and ricorne), varied carper beetle (Anthrenus verbasci), red flour beetle (Tribolium castaneum), powder post beetle (Lyctus Stink bug (Halyomorpha mista); whiteflies (Aleyrodidae) brunneus), white-spotted longicorn beetle (Anoplophora Such as greenhouse whitefly (Trialeurodes vaporariorum), malasiaca), pine shoot beetle (Tomicus piniperda), etc. sweetpotato whitefly (Bemisia tabaci), and silver leaf white 1003 Orthoptera:- fly (Bemisia argentifolii); scales (Coccidae) Such as Cal 1004 Asiatic locust (Locusta migratoria), African mole formia red scale (AOnidiella aurantii), San Jose scale (Com cricket (Gryllotalpa africana), rice grasshopper (Oxya stockaspis perniciosa), citrus north scale (Unaspis citri), red yezoensis), rice grasshopper (Oxya japonicas), etc. wax scale (Ceroplastes rubens), and cottonycushion scale 1005 Hymenoptera:- (Icerya purchasi); lace bags (Tingidae); psyllids (Psyllidae); 1006 Cabbage sawfly (Athalia rosae), Acromyrmex spp., etc. 0995 Lepidoptera:- fire ant (Solenopsis spp.), etc. 0996 Pyralid moths (Pyralidae) such as rice stem borer 1007 Nematodes:- (Chilo suppressalis), yellow rice borer (Tryporyza incertu 1008 Rice white-tip nematode (Aphelenchoides besseyi), las), rice leafroller (Cnaphalocrocis medinalis), cotton lea strawberry bud nematode (Nothotylenchus acris), etc. froller (Notarcha derogata), Indian meal moth (Plodia inter 1009 Dictyoptera:- punctella), oriental corn borer (Ostrinia furnacalis), cabbage 1010 German cockroach (Blattella germanica), smoky webworm (Hellula undalis), and bluegrass webworm (Pedia brown cockroach (Periplaneta fuliginosa), American cock sia teterrellus); Owlet moths (Noctuidae) Such as common roach (Periplaneta americana), Periplaneta brunnea, oriental cutworm (Spodoptera litura), beet armyworm (Spodoptera cockroach (Blatta Orientalis), etc. exigua), armyworm (Pseudaletia separata), cabbage army 1011 Acarina:— worm (Mamestra brassicae), black cutworm (Agrotis ipsi 1012 Spider mites (Tetranychidae) such as two-spotted lon), beet semi-looper (Plusia nigrisigna), Thoricoplusia spider mite (Tetranychus urticae); eriophyid mites (Eriophy spp., Heliothis spp., and Helicoverpa spp., whites and Sulfer idae) such as pink citrus rust mite (Aculops pelekassi); butterflies (Pieridae) such as common white (Pieris rapae); tarosonemid mites (Tarsonemidae) Such as broad mite tortricid moths (Tortricidae) Such as Adoxophyes spp., orien (Polyphagotarisonemus latus); false spider mites (Tenuipal tal fruit moth (Grapholita molesta), soybean podborer (Legu pidae); Tuckerellidae; ticks (Ixodidae) such as Haemaphysa minivora glycinivorella), azuki bean podworm (Matsumu lis longicornis, Haemaphysalis flava, Dermacentor taiwani raeses azukivora), Summer fruit tortrix (Adoxophyesorana fasciata), Adoxophyessp., oriental teatortrix (Homona mag cus, Ixodes ovatus, Ixodes persulcatus, Boophilus microplus, nanima), apple tortrix (Archips fiascocupreanus), and Cydia and Rhipicephalus sanguineus; acarid mites (Acaridae) Such pomonella; leafblotch miners (Gracillariidae) Such as tea lea as mold mite (Trophagus putrescentiae); house dust mites froller (Caloptilia theivora), and apple leafminer (Phyllono (Pyroglyphidae) Such as Dermatophagoides farinae, and rycter ringoneella); Carposinidae Such as peach fruit moth Dermatophagoides ptrenyssinus; cheyletide mites (Chey (Carposina niponensis); lyonetiid moths (Lyonetiidae) Such letidae) Such as Cheyletus eruditus, Cheyletus malaccensis, as Lyonetia spp., tussock moths (Lymantriidae) Such as and Cheyletus moorei: parasitoid mites (Dermanyssidae); Lymantria spp., and Euproctis spp.; yponomeutid moths Dermahyssus gallinae; etc. (Yponomeutidae) Such as diamondback (Plutella xylostella); 1013 Furthermore, the preparation containing the com gelechiid moths (Gelechiidae) such as pink bollworm (Pecti pound (I) or a salt thereof can be used in the field of treatment nophor a gossypiella), and potato tubeworm (Phthorinaea for disease of livestock and in livestock farming, and also for operculella); tiger moths and allies (Arctiidae) Such as fall maintaining public sanitation by exterminating an arthropod webworm (Hyphantria cunea); tineid moths (Tineidae) Such and parasite which parasitize inside and/or outside of Verte as casemaking clothes moth (Tinea translucens), and web brates such as human, cow, sheep,goat, pig, poultry, dog, cat, bing clothes moth (Tineola bisselliella); etc. fish and the like. Examples of pests include, for example, 0997 Thysanoptera:- Ixodes spp., Boophilus spp. (e.g. Boophilus microplus), 0998. Thrips (Thripidae) such as yellow citrus thrips Amblyomma spp., Hyalomma spp., Rhipicephalus spp. (e.g. (Frankliniella occidentalis), Thrips parmi, yellow tea thrips Rhipicephalus appendiculatus), Haemaphysalis spp., derma (Scirtothrips dorsalis), onion thrip (Thrips tabaci), flower thrips (Frankliniella intonsa), etc. centor spp., Ornithodoros spp. (e.g. Ornithodoros moubata), 0999 Diptera:- Dermahyssus gallinae, Ornithonyssus Sylviarum, Sarcoptes 1000 Housefly (Musca domestica), common mosquito spp. (e.g. Sarcoptes scabiei), Psoroptes spp., Chorioptes spp., (Culex popiens pallens), horsefly (Tabanus trigonus), onion Demodex spp., Eutrombicula spp., Aedes spp. (e.g. Aedes maggot (Hylenya antiqua), Seedcorn maggot (Hylenya pla albOpictus), Anopheles spp., Culex spp., Culicodes spp., tura), Anopheles sinensis, rice leafminer (Agromyza Oryzae), Musca spp., Hypoderma spp., Gasterophilus spp., Haemato rice leafminer (Hydrellia griseola), rice stem maggot (Chlo bia spp., Tabanus spp., Simulium spp., Triatoma spp., rops Oryzae), melon fly (Dacus cucurbitae), Ceratitis capi Phthiraptera (e.g. Damalinia spp., Linognathus spp., Hae tata, legume leafminer (Liriomyza trifolii), etc. matopinus spp), Ctenocephalides spp. Xenosylla spp), mono 1001 Coleoptera:- morium pharaonis and Nematoda (for example, Trichos 1002 Twenty-eight-spotted ladybird (Epilachna vigintio trongylus (e.g. Nippostrongylus brasiliensis, ctopunctata), cucurbit leaf beetle (Aulacophora femoralis), Tricho strongylus axei, Trichostrongylus colubriformis), Tri striped flea beetle (Phyllotreta striolata), rice leaf beetle chinella (e.g. Trichinella spiralis), Haemonchus contortus, US 2011/0319437 A1 Dec. 29, 2011 49

Nematodirus (e.g. Nematodirus battus), Ostertagia circum The hydroponic solution treatment is a method of treatment cincta, Cooperia spp., Hymenolepis mana) and the like. for protecting crops from damages by pests, by treating 1014 For the method for controlling pests of the present hydroponic Solution or the like with an active ingredient in invention, the compound (I) or a salt thereofmay be used as it order to penetrate and translocate from the root portion and is. But the compound (I) or a salt there of is usually formu the like into the plant interior of a crop to be protected from lated to the form of above mentioned pesticidal composition damages such as feeding and the like by pests, and specifi of the present invention, and for example, it is applied to apest cally, for example, hydroponic solution incorporation, hydro or a inhabit of pests in a similar manner as conventional ponic solution mixing, and the like are exemplified. pesticidal composition, then the active ingredient being 1018. The amount of application of the compound (I) or a brought the pests into contact or fed the pests. salt thereof in the method for controlling pests of the present 1015 Examples of the habitat of pests in the present inven invention can be changed depending on the application time, tion include paddy fields, fields, orchards, uncultivated fields, application site, application method and the like, but in gen houses and the like. eral, it is at a rate of about 0.3 to 3000 g, preferably at a rate of 1016. As a method for application, for example, a spray about 50 to 3000 g as an amount of the active ingredient (the treatment, a Soil treatment, a seed treatment and a hydroponic compound (I) or a salt thereof) per hectare. In addition, when Solution treatment are exemplified. the pesticidal composition of the present invention is a wet 1017. The spray treatment in the present invention is a table powder or the like, it may be diluted with water to use so method of treatment for expressing a controlling effect that the final concentration of active ingredient comes to the against pests by treating plant Surface or pest itself with an range of about 0.1 to 1,000 ppm, preferably about 10 to 500 active ingredient (the compound (I) or a salt thereof), specifi ppm. cally for example, foliage application, spraying to tree trunk 1019. As an alternative mode, for example, the arthropod and the like. The soil treatment is a method of treatment for and parasite living with said vertebrates can be exterminated protecting crops from damages by pests, by treating soils, in whole body or non-whole body by administering the pes irrigation Solutions or the like with an active ingredient in ticidal composition of the present invention to inside (internal order to penetrate and translocate from the root portion and parts of the body) or outside (body surface) of the above the like into the plant interior of a crop to be protected from mentioned vertebrates. The method of administrating to damages such as feeding and the like by pests, and specifi inside includes oral treatment; anus treatment; interplanting: cally, for example, a planting hole treatment (planting hole and hypodermic treatment, intermuscular treatment or vein spraying, soil-incorporation after planting hole treatment), a treatment by injection. In addition, sanitary pests arising from plant foot treatment (plant foot spraying, plant foot Soil the excrement of the animal can be exterminated by feeding a incorporation, plant foot irrigation, plant foot treatment at livestock animal. latter half of raising seeding period), planting furrow treat 1020 When the pesticidal composition of the present ment (planting furrow spraying, planting furrow soil-incor invention is applied to an animal which a pest is parasitic Such poration), planting row treatment (planting row spraying, as a domestic animal and a pet, the application amount can be planting row soil-incorporation, planting row spraying at varied in wide range according to application method, but, growing period), planting row treatment at Sowing (planting generally, it is preferable that the amount of active ingredient row spraying at Sowing, planting row soil-incorporation at (the compound (I) or a salt thereof) per 1 kg of animal weight Sowing), overall treatment (overall spraying, overall soil-in is about 0.1 mg to 2000 mg, more preferably about 0.5 mg to corporation), other spray treatment (foliar granule spraying at 1000 mg. growing period, spraying under tree crown or around main 1021. The present invention will be further illustrated by stem, Soil Surface spraying, soil Surface incorporation, Sow the following Synthetic Examples, Reference Examples, For ing hole spraying, spraying on the ribbing ground, inter-plant mulation Examples and Test Examples; however, the present spraying), other irrigation treatment (irrigation into soil, irri invention is not limited to these examples. gation during raising seeding, injection treatment of pesticide 1022. The elution in the column chromatography for Solution, irrigation on plant foot, pesticide solution drip irri Examples and Reference Production Examples was carried gation, chemigation), nursery box treatment (nursery box out under the observation by TLC (Thin Layer Chromatog spraying, nursery box irrigation), nursery tray treatment raphy). In the TLC observation, kiesel gel 60Fs (70 to 230 (nursery tray spraying, nursery tray irrigation), nursery bed meshes) manufactured by Merck & Co., Inc. was used as TLC treatment (nursery bed spraying, nursery bed irrigation, nurs plate; the solvent used as an elution solvent in column chro ery bed spraying in paddy field, immersion of nursery plant), matography was used as developing solvent; and a UV detec seedbed soil-incorporation treatment (seedbed soil-incorpo tor was used for detection. Kiesel gel 60 (70 to 230 meshes) ration, seed bed soil-incorporation before sowing), other manufactured by Merck & Co., Inc. was used as silica gel for treatment (growing media incorporation, plowing, Surface column chromatography. As a medium pressure preparative soil-incorporation, soil incorporation into rain dropping, high performance liquid chromatography, Ultrapack manu planting spot treatment, flower cluster granule spraying, paste factured by Yamazen, Co., Ltd. (filler: silica gel) has been fertilizer mixing), and the like are exemplified. The seed used. When a mixed solvent was used as developing solvent, treatment is a method of treatment for expressing a control the numeric value in parentheses shows a mixing ratio of ling effect against pests by treating seeds, seed tubers, bulbs solvents by volume. NMR spectra were proton NMR, and or the like of a crop to be protected from damages such as were determined with JEOL AL-400 (400 MHz) spectrom feeding and the like by pests directly, or neighborhood eter and AVANCE 400 (400MHz) spectrometer using tetram thereof, with an active ingredient, and specifically, for ethylsilane as internal standard. All delta values were shown example, blowing treatment, painting treatment, immersion in ppm. The measurement temperature is 25°C. unless oth treatment, impregnation treatment, application treatment, erwise mentioned, and the measurement temperature has film coating and a pellet coating treatment are exemplified. been indicated for the rest. US 2011/0319437 A1 Dec. 29, 2011 50

1023. Furthermore, the abbreviations used in the follow 1031. The stereochemistry of the -CH=CH-bond was ing Examples and Reference Production Examples have the mixture of E and Z. following meanings: s: singlet, br: broad, brs: broad singlet, d: doublet, t: triplet, q: Example 4 quartet, quint: quintet, Sext: sextet, Sept: Septet, Me: methyl group, Et: ethyl group, Ph: phenyl group, Pr-n (or n-Pr): Compound (4): 2-Chlorophenyl N-phenyl-3-(phe n-propyl, Pr-i (or i-Pr or Pr): isopropyl, Pr-cyclo (or cyclo nylthio)thioacrylimidate Pr): cyclopropyl. Bu-n (or n-Bu): n-butyl, Bu-i (or i-Bu): isobutyl, Bu-s (or S-Bu): sec-butyl, Bu-t (ort-Bu): tert-butyl, 1032 'H-NMR (CDC1) & (ppm): 5.62-5.87 (1H, m), DMF: dimethylformamide, m-CPBA: meta chloro perben 6.83-7.59 (15H, m) Zoic acid. In addition, room temperature means about 15 to 1033. The stereochemistry of the -CH=CH-bond was 250 C. mixture of E and Z. Example 1 Example 5 Compound (I): Phenyl N-phenyl-3-(phenylthio)thio Compound (5): Benzyl N-phenyl-3-(phenylthio)thio acrylimidate acrylimidate 1024 N-phenyl-3-phenylthioacrylamide (0.75 g) was sus 1034 'H-NMR (CDC1) & (ppm): 4.31 (2H, s), 6.08 (1H, pended to toluene (10 ml), then thionyl chloride (0.40 ml), d J=15.6 Hz), 6.74 (2H, d J=7.3 Hz), 7.05 (1H, tJ=7.4 Hz), one drop of DMF and triethylamine (0.80 ml) were added 7.22-7.39 (13H, m). thereto at room temperature. The mixture was stirred on the 1035. The stereochemistry of the -CH=CH-bond was 60° C. oil bath for three hours. Then it was cooled and filtered E. off the insoluble matter. The filtrate was concentrated under reduced pressure. The residue was dissolved to DMF (15 ml). Example 6 Sodium hydride (55% in oil: 0.217 g) was added thereto under ice-cooling, then thiophenol (0.40 ml) was added drop Compound (6): Benzyl N-phenyl-3-(benzylthio)thio wise over the period for 3 minutes. It was stirred for 2.5 hours. acrylimidate Aqueous saturated sodium chloride solution (10 ml) and water (5 ml) were added to the reaction mixture, and it was 1036) H-NMR (CDC1) & (ppm): 3.82 (2H, s), 4.30 (2H, extracted with t-butyl methyl ether (15 ml) three times. The s), 6.07 (1H, d J=15.6 Hz), 6.73 (2H, d J=7.6 Hz), 7.07 (1H, organic layers were combined, and washed with aqueous tJ–74 Hz), 7.14-7.39 (13H, m). saturated sodium chloride solution (15 ml) three times, dried 1037. The stereochemistry of the -CH=CH-bond was over anhydrous sodium sulfate, filtered off an inorganic salt, E. concentrated under reduced pressure, to obtain black oil (1.0 g). It was subjected to silica gel column chromatography Example 7 (hexane:ethyl acetate=15:1) to obtain phenyl N-phenyl-3- (phenylthio)thioacrylimidate (0.41 g) as light yellow oil. Compound (7): Phenyl N-phenyl-3-(cyclohexylthio) 1025 H-NMR (CDC1)8(ppm): 5.68 (d.J=15.1 Hz), 5.81 thioacrylimidate (d J=10.3 Hz), 6.08 (d.J=15.1 Hz) total 1H, 6.66-7.58 (16H, m) 1038 H-NMR (CDC1) & (ppm): 1.20-2.00 (10H, m), 1026. The stereochemistry of the —CH=CH-bond was 2.66-2.92 (1H, m), 5.71 (0.33H, d J=12.0 Hz), 5.77 (0.66H, d mixture of E and Z. J=15.1 Hz), 6.92-7.51 (11H, m) 1027 Compounds (2) to (34) were synthesized in a similar 1039 The stereochemistry of the -CH=CH-bond was manner as the Example 1. mixture of E and Z. Example 2 Example 8 Compound (8): Phenyl N-phenyl-3-(benzylthio)thio Compound (2): 4-Chlorophenyl N-phenyl-3-(phe acrylimidate nylthio)thioacrylimidate 1040 'H-NMR (CDC1,) & (ppm): 3.75 (1H, m), 3.86 (1H, 1028 H-NMR (CDC1) & (ppm): 5.46-5.84 (1H, m), m), 5.70 (0.5H, d, J=12.0 Hz), 5.79 (0.5H, d, J=16.0 Hz), 6.67-7.52 (15H, m) 6.62-7.52 (16H, m) 1029. The stereochemistry of the -CH=CH-bond was 1041. The stereochemistry of the —CH=CH-bond was mixture of E and Z. mixture of E and Z. Example 3 Example 9 Compound (3): 3-Chlorophenyl N-phenyl-3-(phe Compound (9): Phenyl N-phenyl-3-(phenylthio)thio nylthio)thioacrylimidate acrylimidate 1030 "H-NMR (CDC1) & (ppm): 5.55-5.87 (1H, m), 1042 'H-NMR (CDC1) & (ppm): 5.81 (1H, d J=10.1 Hz), 6.67-7.63 (15H, m) 6.84 (1H, d J=10.1 Hz), 7.08-7.52 (15H, m).

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1093. The stereochemistry of the -CH=CH-bond was 1100I 'H-NMR (CDC1) & (ppm): 6.01 (0.67H, d J=14.7 mixture of E and Z. Hz), 6.35 (0.33H, d J=9.9 Hz), 7.20 (0.33H, d J=9.9 Hz), 7.31-7.51 (15H, m), 7.85 (0.67H, d J=14.7 Hz) Example 34 1101 The stereochemistry of the —CH=CH-bond was mixture of E and Z. Compound (34): 2,3-Dichlorophenyl N-phenyl-3- (phenylthio)thioacrylimidate Example 37 1094 'H-NMR (CDC1) & (ppm): 5.54 (0.5H, d J=14.6 Compound (37): Phenyl N-phenyl-3-(phenylthio) Hz), 5.77 (0.38H, d J=10.2 Hz), 6.05 (0.12H, d J=15.4 Hz), acrylimidate 6.67-7.62 (14H, m) 1102 N-phenyl-3-phenylthioacrylamide (0.766 g) was 1095. The stereochemistry of the -CH=CH-bond was suspended to toluene (15 ml), then thionyl chloride (0.33 ml) mixture of E and Z. and triethylamine (0.62 ml) were added thereto at room tem perature. The mixture was stirred on the 60° C. oil bath for Example 35 three hours. Then it was filtered off the insoluble matter. The Compound (35): Phenyl N-phenyl-3-(phenoxy)thio filtrate was concentrated under reduced pressure. The residue acrylimidate was dissolved to DMF (15 ml). 1103 Sodium hydride (55% in oil: 0.226 g) was added 1096 N-phenyl-3-phenoxyacrylamide (1.5 g) was sus thereto under ice-cooling, then phenol (0.303 g) was added. It pended to toluene (80 ml), then thionyl chloride (0.82 ml), was stirred for 2.5 hours under ice-cooling and for overnight triethylamine (1.8 ml) and one drop of DMF were added at room temperature. Aqueous saturated Sodium chloride thereto at room temperature. The mixture was stirred on the solution (15 ml) and water (5 ml) were added to the reaction 60° C. oil bath for three hours. Then it was cooled and filtered mixture, and it was extracted with ethyl acetate (20 ml) and off the insoluble matter. The filtrate was concentrated under t-butyl methyl ether (15 ml) twice. The organic layers were reduced pressure. The residue was dissolved to DMF (80 ml). combined, and washed with aqueous Saturated Sodium chlo Sodium salt of thiophenol (0.82 g) was added to it under ride solution (15 ml) three times, dried over anhydrous ice-cooling, and stirred for 2 hours. t-Butyl methyl ether (250 Sodium Sulfate, filtered off an inorganic salt, concentrated ml) was added to the reaction mixture. It was successively under reduced pressure to obtain black oil (0.88 g) It was washed with 1N aqueous sodium hydroxide solution, water Subjected to silica gel column chromatography (hexane:ethyl and aqueous saturated Sodium chloride Solution, dried over acetate=15:1) to obtain phenyl N-phenyl-3-(phenylthio) anhydrous Sodium Sulfate, filtered off an inorganic salt, con acrylimidate (0.2 g) as light yellow oil. centrated under reduced pressure. The residue was isolated 1104) 'H-NMR (CDC1) & (ppm): 5.65-5.90 (1H, m), and purified by silica gel column chromatography (hexane: 6.72-7.72 (16H, m) ethyl acetate=20:1) to obtain phenyl N-phenyl-3-(phenoxy) 1105 The stereochemistry of the -CH=CH-bond was thioacrylimidate (0.28 g) as yellow oil. mixture of E and Z. 1097 H-NMR (CDC1) & (ppm): 5.64 (0.7H, d, J=12.00 1106 Compounds (38) to (98) were synthesized in a simi Hz), 5.98 (0.3H, d, J=12.0 Hz), 6.75 (0.6H, d, J=7.6 Hz), lar manner as the Example 37. 6.91-744 (13.8H, m), 7.59 (0.6H, d, J=6.6 Hz), 7.68 (1H, d, J=12.0 Hz) Example 38 1098. The stereochemistry of the -CH=CH-bond was Compound (38): Phenyl 3-(phenoxy)-N-pheny mixture of E and Z. lacrylimidate Example 36 1107] 'H-NMR (CDC1)8(ppm):5.74 (1H,d, J=12.4Hz), 6.78-6.81 (2H, m), 7.00-7.44 (13H, m), 7.80 (1H, d. J=12.4 Compound (36): Phenyl N-phenylsulfonyl-3-(phe Hz) nylthio)thioacrylimidate 1108 The stereochemistry of the —CH=CH-bond was E. 1099 N-phenylsulfonyl-3-phenylthioacrylamide (0.50 g) was suspended to toluene (10 ml), then thionyl chloride (0.20 Example 39 ml), triethylamine (0.40 ml) and one drop of DMF were added thereto at room temperature. The mixture was stirred on the Compound (39): Phenyl N-(2-chlorophenyl)-3-(phe 60° C. oil bath for three hours. Then it was cooled and filtered nylthio)acrylimidate off the insoluble matter. The filtrate was concentrated under 1109 'H-NMR (CDC1) & (ppm): 5.69 (0.83H, d J=15.2 reduced pressure. The residue was dissolved to DMF (8 ml). Hz), 5.81 (0.17H, d J=15.0 Hz), 6.73 (0.83H, d J=7.7 Hz), DMF (2 ml) solution of sodium salt of thiophenol (0.30 g) was 6.88-7.00 (0.83H, m), 7.05-7.55 (12.34H, m), 7.74 (0.83H, d added thereto under ice-cooling, and it was stirred at room J=15.2 Hz), 8.00 (0.17H, d J=15.0 Hz) temperature for 1.5 hours. Ethyl acetate (80 ml) was added to 1110 The stereochemistry of the —CH=CH-bond was the reaction mixture, and it was successively washed with 1N mixture of E and Z. aqueous sodium hydroxide Solution, water and aqueous Satu rated Sodium chloride solution, dried over anhydrous sodium Example 40 Sulfate, filtered off an inorganic salt, concentrated under reduced pressure. The residue was isolated and purified by Compound (40): Phenyl N-(3-chlorophenyl)-3-(phe silica gel column chromatography (hexane:ethyl acetate-10: nylthio)acrylimidate 1) to obtain phenyl N-phenylsulfonyl-3-(phenylthio)thio 1111 H-NMR (CDC1) & (ppm): 5.75 (0.83H, d J=15.0 acrylimidate (0.14 g) as light yellow oil. Hz), 5.81 (0.17H, d J=15.0 Hz), 6.56-6.63 (0.83H, m), 6.71

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1229 The stereochemistry of the —CH=CH-bond was 1241 The stereochemistry of the —CH=CH-bond was E. E. Example 99 Example 103 Compound (99): Phenyl N-phenyl-3-(phenylsulfo Compound (103): Phenyl 3-(4-fluorophenylthio)-N- nyl)acrylimidate phenylacrylimidate 1230 Phenyl N-phenyl-3-(phenylthio)acrylimidate (3.65 g) was dissolved to chloroform (50 ml), m-CPBA (70%:5.42 1242 'H-NMR (CDC1) & (ppm): 5.76(1H, d, J=15.2 Hz), g) was added thereto in five portion under ice-cooling, then it 6.70 (2H, d, J=7.2 Hz), 6.98-7.42 (12H, m), 7.61 (1H, d, was stirred for two hours at the same temperature. Then J=15.2 Hz). chloroform (50 ml) and aqueous saturated sodium bicarbon 1243. The stereochemistry of the —CH=CH-bond was ate solution (75 ml) were added and extracted. The organic E. layer was washed with aqueous Saturated Sodium chloride solution (50 ml), dried, distilled off the solvent. The residue Example 104 was subjected to silica gel column chromatography (hexane: ethyl acetate=3:1) to obtain phenyl N-phenyl-3-(phenylsul Compound (104): Phenyl 3-(2-fluorophenylthio)-N- fonyl)acrylimidate (2.08 g) as light yellow crystal. phenylacrylimidate 1231 m.p.: 110-116° C. 1244. H-NMR (CDC1) & (ppm): 5.81 (1H, d, J=14.9 Hz), 1232 'H-NMR (CDC1) & (ppm): 6.73-6.75H (2H, m), 6.72 (2H, d, J=7.3 Hz), 6.97-7.46 (12H, m), 7.58 (1H, d, 7.04 (1H, d, J=15.0 Hz), 7.10-7.91 (14H, m) J=15.1 Hz). 1233. The stereochemistry of the -CH=CH-bond was 1245. The stereochemistry of the —CH=CH-bond was mixture of E and Z. E. Example 100 Example 105 Compound (100): Phenyl 3-(2-bromophenylthio)-N- Compound (105): Phenyl 3-(2-methylphenylthio)-N- phenylacrylimidate phenylacrylimidate 1234 Sodium hydride (60% in oil: 0.026 g) was sus pended to DMF (2 ml), and 2-bromothiophenol (0.10 g) was 1246) "H-NMR (CDC1) & (ppm): 2.38 (3H, s), 5.65 (1H, added there to under ice-cooling. Furthermore, phenyl d, J=15.0 Hz), 6.69 (2H, d, J=7.5 Hz), 6.95-7.42 (12H, m), N-phenyl-3-(phenylsulfonyl)acrylimidate (0.20 g) was 7.61 (1H, d, J=15.0 Hz). added thereto, and stirred for one hour under ice-cooling. 1247 The stereochemistry of the —CH=CH-bond was After the reaction, water and ethyl acetate were added to the E. reaction mixture, and extracted. The organic layer was washed with aqueous Saturated sodium chloride solution, Example 106 dried, and distilled off the solvent. The residue was subjected to silica gel column chromatography (hexane:ethyl Compound (106): Phenyl 3-(3-methylphenylthio)-N- acetate=10:1) to obtain phenyl 3-(2-bromophenylthio)-N- phenylacrylimidate phenylacrylimidate (0.19 g). 1248 H-NMR (CDC1) & (ppm): 2.32 (3H, s), 5.87 (1H, 1235 H-NMR (CDC1) & (ppm): 5.90 (1H, d, J=15.1 Hz), d, J=15.2 Hz), 6.73 (2H, d, J=7.2 Hz), 6.98-7.39 (12H, m), 6.74 (2H, d. J=7.6 Hz), 6.98-7.64 (13H, m). 7.69 (1H, d, J=15.2 Hz). 1236. The stereochemistry of the —CH=CH-bond was 1249. The stereochemistry of the —CH=CH-bond was E. E. 1237 Compounds (101) to (130) were synthesized in a similar manner as the Example 100. Example 107 Example 101 Compound (107): Phenyl 3-(3-methoxyphenylthio)- N-phenylacrylimidate Compound (101): Phenyl 3-(3-bromophenylthio)-N- phenylacrylimidate 1250 'H-NMR (CDC1) & (ppm): 3.79 (3H, s), 5.91 (1H, 1238 H-NMR (CDC1) & (ppm): 5.92(1H, d, J=15.2 Hz), d, J=15.2 Hz), 6.73 (2H, d, J=7.5 Hz), 6.83-7.39 (12H, m), 6.73 (2H, d, J=7.7 Hz), 6.98-7.67 (13H, m). 7.70 (1H, d, J=15.0 Hz). 1239. The stereochemistry of the -CH=CH-bond was 1251. The stereochemistry of the -CH=CH-bond was E. E. Example 102 Example 108 Compound (102): Phenyl 3-(4-bromophenylthio)-N- Compound (108): Phenyl 3-(4-nitrophenylthio)-N- phenylacrylimidate phenylacrylimidate 1240 H-NMR (CDC1) & (ppm): 5.85 (1H, d. J=15.4 Hz), 1252 'H-NMR (CDC1) & (ppm): 6.15 (1H, d, J=15.2 Hz), 6.71 (2H, d, J=7.8 Hz), 7.02-7.46 (12H, m), 7.62 (1H, d, 6.76 (2H, d, J=7.2 Hz), 7.03-7.53 (10H, m), 7.70 (1H, d, J=15.1 Hz). J=15.2 Hz), 8.19 (2H, d, J=8.9 Hz).

US 2011/0319437 A1 Dec. 29, 2011

1280 The stereochemistry of the —CH=CH-bond was 1294 The stereochemistry of the —CH=CH-bond was E. E. Example 121 Example 127 Compound (121): Phenyl 3-(3,5-dimethylphe Compound (127): Phenyl 3-(2-chloro-5-pyridinylm nylthio)-N-phenylacrylimidate ethylthio)-N-phenylacrylimidate 1281 H-NMR (CDC1) & (ppm): 2.28 (6H, s), 5.85 (1H, 1295 H-NMR (CDC1) & (ppm): 3.85 (2H, s), 5.77 (1H, d, J=15.0 Hz), 6.73 (2H, d, J=7.2 Hz), 6.92-7.39 (11H, m), d, J=15.2 Hz), 6.70 (2H, d, J=6.7 Hz), 7.02-7.52 (11H, m), 7.69 (1H, d, J=15.2 Hz). 8.23 (1H, s). 1282. The stereochemistry of the —CH=CH-bond was 1296. The stereochemistry of the -CH=CH-bond was E. E. Example 122 Example 128 Compound (122): Phenyl 3-2-(1-methylethyl)phe Compound (128): Phenyl 3-(2-chloro-5-thiazolylm nylthio-N-phenylacrylimidate ethylthio)-N-phenylacrylimidate 1283 H-NMR (CDC1) & (ppm): 1.18 (6H, d, J=7.5 Hz), 1297 'H-NMR (CDC1) & (ppm): 4.00 (2H, s), 5.84 (1H, 3.36-3.43 (1H, m), 5.65 (1H, d, J=15.0 Hz), 6.67 (2H, d, J=7.2 d, J=15.1 Hz), 6.71-7.40 (11H, m), 7.49 (1H, d, J=15.1 Hz). Hz), 6.93-7.42 (12H, m), 7.64 (1H, d. J=15.0 Hz). 1298. The stereochemistry of the -CH=CH-bond was 1284. The stereochemistry of the —CH=CH-bond was E. E. Example 129 Example 123 Compound (129): Phenyl 3-(2-chloro-5-thienylmeth Compound (123): Phenyl N-phenyl-3-(4-trifluorom ylthio)-N-phenylacrylimidate ethylphenylthio)acrylimidate 1299 H-NMR (CDC1) & (ppm): 4.00 (2H, s), 5.86 (1H, 1285 H-NMR (CDC1)8(ppm):5.97 (1H,d, J=15.0Hz), d, J=15.2 Hz), 6.52-7.39 (12H, m), 7.53 (1H, d, J=15.0 Hz). 6.73 (2H, d, J=7.3 Hz), 6.99-7.59 (12H, m), 7.67 (1H, d, 1300. The stereochemistry of the -CH=CH-bond was J=15.2 Hz). E. 1286. The stereochemistry of the —CH=CH-bond was E. Example 130 Example 124 Compound (130): Phenyl 3-(4-methylphenylthio)-N- (phenyl)thioacrylimidate Compound (124): Phenyl 3-(4,6-dimethyl-2-pyrim idinylthio)-N-phenylacrylimidate 1301 H-NMR (CDC1) & (ppm): 2.33 (3H, s), 5.58 (1H, d, J=14.5 Hz), 6.90-7.56 (15H, m). 1287 m.p.: 175-178° C. 1302. The stereochemistry of the -CH=CH-bond was 1288 H-NMR (CDC1) & (ppm): 2.44 (6H, s), 6.24 (1H, E. d, J=15.9 Hz), 6.80 (3H, d, J=6.9 Hz), 7.04-7.43 (8H, m), 8.63 (1H, d, J=15.9 Hz). Example 131 1289. The stereochemistry of the -CH=CH-bond was E. Compound (131): Phenyl N-phenyl-3-(N-acetyl-N'- phenylamino)acrylimidate Example 125 1303. To DMF (3 ml) solution of acetanilide (0.14 g) was Compound (125): Phenyl 3-(3-chlorophenylthio)-N- added sodium hydride (60% in oil: 0.043 g) under ice-cool phenylacrylimidate ing, and DMF (2 ml) solution of phenyl N-phenyl-3-(phenyl sulfonyl)acrylimidate (0.30 g) was added dropwise. It was 1290 m.p.: 85°C. stirred for two hours under ice-cooling and for one hour at 1291 H-NMR (CDC1) & (ppm): 5.92(1H, d, J=15.2 Hz), room temperature. Ethyl acetate (100 ml) was added to the 6.73 (2H, d, J–7.5 Hz), 7.01 (1H, t, J–7.5 Hz), 7.15-7.45 reaction mixture and was successively washed with water and (11H, m), 7.64 (1H, d. J=15.2 Hz). aqueous Saturated Sodium chloride solution. The organic 1292. The stereochemistry of the -CH=CH-bond was layer was dried over anhydrous magnesium sulfate, concen E. trated under reduced pressure. The residue was isolated and purified by silica gel column chromatography (hexane:ethyl Example 126 acetate=3:1) to obtain phenyl N-phenyl-3-(N-acetyl-N'-phe Compound (126): Phenyl 3-(2-chlorophenylthio)-N- nylamino)acrylimidate (0.050 g) as yellow crystal. phenylacrylimidate 1304 m.p.: 120° C. 1305 H-NMR (CDC1) & (ppm): 1.94 (3H, s), 4.72 (1H, 1293 'H-NMR (CDC1) & (ppm): 5.88 (1H, d, J=15.0 Hz), d, J=14.00 Hz), 6.57 (2H, d, J–7.5 Hz), 6.85-6.87 (1H, m), 6.69-6.92 (2H, m), 6.95-7.12 (1H, m), 7.14-7.51 (11H, m), 7.03-7.22 (7H, m), 7.35-7.39 (5H, m), 8.66 (1H, d, J=14.0 7.52 (1H, d, J=15.0 Hz). Hz). US 2011/0319437 A1 Dec. 29, 2011 62

1306 The stereochemistry of the —CH=CH-bond was ice-cooling, and stirred for 30 minutes at the same tempera E. ture. Phenyl 3-phenoxy-N-phenylacrylimidate (0.30 g) was dissolved to DMF (2 ml), and the obtained solution was added Example 132 to the above mentioned thiolate solution under ice-cooling, Compound (132): Phenyl 3-(N-methyl-N'-pheny and stirred for two hours at the same temperature and for two lamino)-N-phenylacrylimidate hours at room temperature. Ethyl acetate (100 ml) was added to the reaction solution, and it was successively washed with 1307 phenyl 3-(phenoxy)-N-phenylacrylimidate (0.39 g) 1N aqueous Sodium hydroxide solution, water and aqueous was dissolved to acetonitrile (5 ml), and N-methylaniline saturated sodium chloride Solution, dried over magnesium (0.20 g) and catalytic amount of N,N-dimethylaminopyridine Sulfate (anhydrous), concentrated under reduced pressure. were added at room temperature. It was stirred for two hours The residue was subjected to silica gel column chromatogra at the same temperature and for eight hours under heat reflux phy (hexane:ethyl acetate=10:1) to obtain phenyl 3-ethylthio ing. It was concentrated under reduced pressure. The residue N-phenylacrylimidate (0.14 g) as yellow oil. was subjected to silica gel column chromatography (hexane: 1321 'H-NMR (CDC1) & (ppm): 1.29 (3H, t, J=8.0 Hz), ethyl acetate=10:1) to obtain phenyl 3-(N'-methyl-N'-pheny 2.71 (2H, q, J=8.0 Hz), 5.80 (1H, d, J=16.0 Hz), 6.78 (2H, d, lamino)-N-phenylacrylimidate (0.17 g) as light brown crys J=8.0 Hz), 7.00-7.03 (1H, m), 7.15-7.27 (5H, m), 7.36-7.40 tal. (2H, m), 7.60 (1H, d. J=16.0 Hz) 1308 m.p.: 130-132° C. 1322 The stereochemistry of the —CH=CH-bond was 1309 'H-NMR (CDC1) & (ppm): 3.11 (3H, s), 4.92 (1H, E. d, J=16.0 Hz), 6.86 (2H, d. J=8.0 Hz), 6.99-7.38 (13H, m), 1323 Compounds (137) to (147) were synthesized in a 7.95 (1H, d, J=16.0 Hz). similar manner as the Example 136. 1310. The stereochemistry of the -CH=CH-bond was E. Example 137 1311 Compounds (133) to (135) were synthesized in a Compound (137): Phenyl N-phenyl-3-(propylthio) similar manner as the Example 132. acrylimidate Example 133 1324 'H-NMR (CDC1) & (ppm): 0.95 (3H, t, J=8.0 Hz), Compound (133): Phenyl 3-(N-benzyl-N'-methy 1.60- 1.69 (2H, m), 2.66 (2H, t, J=8.0 Hz), 5.80 (1H, d, J=16.0 lamino)-N-phenylacrylimidate Hz), 6.78 (2H, d, J=8.00 Hz), 7.00-7.03 (1H, m), 7.15-7.27 (5H, m), 7.36-7.40 (2H, m), 7.59 (1H, d, J=16.0 Hz). 1312 H-NMR (CDC1) & (ppm): 2.65 (3H, s), 4.28 (2H, 1325. The stereochemistry of the -CH=CH-bond was s), 4.51 (0.25H, d, J=4.0 Hz), 4.59 (0.75H, d, J=16.0 Hz), E. 6.76-7.46 (15H, m), 7.62 (0.75H, d, J=16.0 Hz), 8.93 (0.25H, d, J=4.0 Hz) Example 138 1313. The stereochemistry of the -CH=CH-bond was Compound (138): Phenyl 3-hexylthio-N-pheny mixture of E and Z. lacrylimidate Example 134 1326 'H-NMR (CDC1) & (ppm): 0.88 (3H, t, J=8.0 Hz), Compound (134): Phenyl N-phenyl-3-(piperidino) 1.23-1.34 (6H, m), 1.55-1.64 (2H, m), 2.67 (2H, t, J=8.0 Hz), acrylimidate 5.79 (1H, d, J=16.0 Hz), 6.78 (2H, d, J=8.0 Hz), 7.00-7.03 (1H, m), 7.15-7.27 (5H, m), 7.36-7.40 (2H, m), 7.60 (1H, d, 1314 m.p.: 127-128°C. J=16.0 Hz). 1315) 'H-NMR (CDC1,) & (ppm): 1.56 (6H, brs), 3.07 1327. The stereochemistry of the -CH=CH-bond was (4H, brs), 4.58 (1H, d. J=16.0 Hz), 6.82 (2H, d, J–4.0 Hz), E. 6.94-6.97 (1H, m), 7.11-7.37 (H, m). 1316. The stereochemistry of the —CH=CH-bond was Example 139 E. Compound (139): Phenyl 3-(1-methylethylthio)-N- Example 135 phenylacrylimidate Compound (135): Phenyl 3-(morphorino)-N-pheny 1328 H-NMR (CDC1) & (ppm): 1.32 (6H, d, J=8.0 Hz), lacrylimidate 3.19 (1H, sept., J=8.0 Hz), 5.85 (1H, d, J=16.0 Hz), 6.79 (2H, d, J=8.0Hz), 6.99-7.03 (1H, m), 7.16-7.26 (5H, m), 7.36-7.40 1317 m.p.: 146-147 C. (2H, m), 7.62 (1H, d. J=16.0 Hz). 1318 H-NMR (CDC1) & (ppm): 3.10 (4H, t, J=4.0 Hz), 1329. The stereochemistry of the -CH=CH-bond was 3.68 (4H, t, J=4.0 Hz), 4.67 (1H, d, J=16.0 Hz), 6.81 (2H, d, E. J=4.0 Hz), 6.95-6.99 (1H, m), 7.11-7.38 (8H, m). 1319. The stereochemistry of the -CH=CH-bond was Example 140 E. Compound (140): Phenyl 3-(1,1-dimethylethylthio)- Example 136 N-phenylacrylimidate Compound (136): Phenyl 3-ethylthio-N-pheny 1330 m.p.: 134-136° C. lacrylimidate 1331 'H-NMR (CDC1) & (ppm): 1.42 (9H, s), 5.97 (1H, d, J=16.0 Hz), 6.77 (2H, d, J=8.0 Hz), 6.99-7.03 (1H, m), 1320 Ethanethiol (0.11 ml) was dissolved to DMF (3 ml), 7.16-7.26 (5H, m), 7.37-7.41 (2H, m), 7.72 (1H, d, J=16.0 and sodium hydride (60% in oil: 60 mg) was added under Hz). US 2011/0319437 A1 Dec. 29, 2011

1332 The stereochemistry of the —CH=CH-bond was 1342 The stereochemistry of the —CH=CH-bond was E. E. Example 141 Example 146 Compound (146): Phenyl 3-(4-methoxyphenylthio)- Compound (141): Phenyl N-phenyl-3-(2-phenyleth N-phenylacrylimidate ylthio)acrylimidate 1343 'H-NMR (CDC1) & (ppm): 3.79 (3H, s), 5.69 (1H, 1333 H-NMR (CDC1) & (ppm): 2.85-2.97 (4H, m), 5.87 d, J=16.0Hz), 6.69 (1H, d, J=8.0 Hz), 6.84 (2H, d, J=8.0 Hz), (1H, d, J=16.0 Hz), 6.80 (2H, d, J=8.0Hz), 7.01-7.06(3H, m), 6.95-7.38 (11H, m), 7.62 (1H, d, J=16.0 Hz). 7.16-7.29 (8H, m), 7.37-7.41 (2H, m), 7.58 (1H, d, J=16.0 1344. The stereochemistry of the —CH=CH-bond was Hz). E. 1334 The stereochemistry of the —CH=CH-bond was Example 147 E. Compound (147): Benzyl 3-benzyloxy-N-pheny Example 142 lacrylimidate 1345 H-NMR (CDC1) & (ppm): 4.73 (2H, s), 5.27 (1H, Compound (142): Phenyl 3-dodecylthio-N-pheny d, J=12.4 Hz).5.30 (2H, s), 6.78-6.80 (2H, m), 701-7.06 (1H, lacrylimidate m), 7.22-7.48 (13H, m). 1346. The stereochemistry of the —CH=CH-bond was 1335 H-NMR (CDC1) & (ppm): 0.88 (3H, t, J=6.8 Hz), E. 1.22-1.34 (18H, m), 1.56-1.64 (2H, m), 2.67 (2H, t, J–7.5 Hz), 5.79 (1H, d, J=15.2 Hz), 6.78 (2H, d, J=7.5 Hz), 6.99-7. Example 148 03 (1H, m), 7.16-7.26 (5H, m), 7.36-7.40 (2H, m), 7.60 (1H, Compound (148): Phenyl 3-methylthio-N-pheny d, J=15.2 Hz). lacrylimidate 1336. The stereochemistry of the -CH=CH-bond was E. 1347 Phenyl 3-phenoxy-N-phenylacrylimidate (0.30 g) was dissolved to THF (5 ml), sodium salt of methyl mercap tan (0.075 g) was added thereto and stirred for four hours at Example 143 room temperature. Ethyl acetate (50 ml) was added to the reaction solution, and it was successively washed with water Compound (143): Phenyl 3-allylthio-N-pheny and aqueous saturated of sodium chloride solution, dried over lacrylimidate magnesium Sulfate (anhydrous), concentrated under reduced pressure. The residue was subjected to silica gel column 1337 'H-NMR (CDC1) & (ppm): 3.33 (2H, d, J-7.00 Hz), chromatography (hexane:ethyl acetate=10:1) to obtain phe 5.00 (1H, d, J=10.9 Hz), 5.12 (1H, d, J=10.1 Hz), 5.70-5.80 nyl 3-methylthio-N-phenylacrylimidate (0.20 g) as yellow (1H, m), 5.89 (1H, d, J=15.6 Hz), 6.76 (2H, d, J–7.5 Hz), 7.02 oil. (1H, t, J=7.4 Hz), 7.15-7.26 (5H, m), 7.35-7.39 (2H, m), 7.54 1348 H-NMR (CDC1) & (ppm): 2.22 (3H, s), 5.72 (1H, (1H, d, J=15.6 Hz). d, J=16.0 Hz), 6.79 (2H, d, J=8.0 Hz), 7.00-7.04 (1H, m), 1338. The stereochemistry of the -CH=CH-bond was 7.17-7.27 (5H, m), 7.36-7.40 (2H, m), 7.65 (1H, d, J=16.0 E. Hz). 1349 The stereochemistry of the —CH=CH-bond was Example 144 E. Compound (144): Phenyl 3-(2-naphthylthio)-N-phe Example 149 nylacrylimidate Compound (149): N-Benzyl-N-methyl-N'-phenyl-3- phenylthioacrylamidine 1339 H-NMR (CDC1) & (ppm): 5.93 (1H, d, J=15.2 Hz), 1350 N-phenyl-3-phenylthioacrylamide (0.77 g) was sus 6.72 (2H, d, J–7.5 Hz), 6.92-6.94 (1H, m), 7.13-7.22 (5H, m), pended to toluene (15 ml), then one drop of DMF and thionyl 7.35-7.39 (2H, m), 7.45-7.53 (3H, m), 7.75-7.83 (4H, m), chloride (0.52 ml) was added thereto at room temperature. 7.92 (1H, brs). The mixture was stirred on the 60° C. oil bath for one hour. 1340. The stereochemistry of the —CH=CH-bond was Then it was cooled and concentrated under reduced pressure. E. The residue was dissolved to THF (15 ml). Benzyl methyl amine (0.77ml) was added thereto at room temperature and Example 145 stirred for 4.5 hours. The unsolved matter was filtered off and concentrated to obtain brown oil (1.39 g). It was subjected to Compound (145): Phenyl N-phenyl-3-(1-phenyleth activated alumina column chromatography (hexane:ethyl ylthio)acrylimidate acetate=20:1) to obtain N-benzyl-N-methyl-N'-phenyl-3- (phenylthio)acrylamidine (0.22 g) as light yellow oil. 1341 'H-NMR (CDC1) & (ppm): 1.60 (3H, d, J–7.0 Hz), 1351 H-NMR (CDC1) & (ppm): 2.95 (3H, s), 4.59 4.14-4.20(1H, m), 5.80 (1H, d, J=15.2 Hz), 6.68 (2H, d, J–7.2 (1.4H, s), 4.62 (0.6H, s), 5.94 (0.7H, d, J=16.2 Hz), 6.01 Hz), 7.03 (1H, t, J=7.4 Hz), 7.13-7.37 (12H, m), 7.49 (1H, d, (0.3H, d, J=10.6 Hz), 6.45 (0.3H, d, J=10.6 Hz), 6.53 (0.7H, J=15.2 Hz). d, J=16.2 Hz), 6.67-6.90 (2H, m), 7.13-7.38 (13H, m) US 2011/0319437 A1 Dec. 29, 2011 64

1352. The stereochemistry of the -CH=CH-bond was umn chromatography (hexane:ethyl acetate-7:1) to obtain mixture of E and Z. N-methyl-N-phenyl-N'-phenyl-3-(4-chlorophenylthio)acry lamidine (0.22 g) as light yellow oil. Example 150 1359 'H-NMR (CDC1,) & (ppm): 3.41 (3H, s), 5.72 Compound (150): Ethyl N-phenyl-3-(phenylthio) (0.8H, d, J=15.9 Hz), 5.92 (0.2H, d, J=10.3 Hz), 6.52-7.41 acrylimidate (15H, m) 1360. The stereochemistry of the -CH=CH-bond was 1353 N-phenyl-3-(phenylthio)acrylamide (2.0 g) was mixture of E and Z. dissolved to chloroform (10 ml), and 7.8 ml of tetrafluorobo 1361 Compound (153) was synthesized in a similar man ric acid triethyloxonium-dichloromethane 1 mol/L solution ner as the Example 152. was added thereto dropwise under ice-cooling. It was stirred for one hour at room temperature, 50° C. for two hours and for Example 153 five hours under heat refluxing. After cooling, ice-water was added to the reaction solution, then the chloroform layer was Compound (153): N,N-Dimethyl-N'-phenyl-3-(4- separated. The chloroform layer was washed with water, methylphenylthio)acrylamidine dried and distilled off the solvent. The residue was subjected to silica gel column chromatography (hexane/ethyl 1362 'H-NMR (CDC1) & (ppm): 2.30 (2.4H, s), 2.32 acetate=15/1) to obtain ethyl N-phenyl-3-(phenylthio) (0.6H, s), 2.98 (4.8H, s), 3.08 (1.2H, s), 5.77 (0.8H, d, J=15.8 acrylimidate (0.15g) as oil. Hz), 5.83 (0.2H, d, J=10.7 Hz), 6.42 (0.2H, d, J=10.7 Hz), 1354 'H-NMR (CDC1) & (ppm): 1.35 (1.8H, t, J=8.4 Hz), 6.45 (0.8H, d, J=15.8 Hz), 6.68-7.73 (2H, m), 6.81-7.29 (7H, 1.51 (1.2H, t, J=8.4 Hz), 4.28 (1.2H, q, J=8.4 Hz), 4.39 (0.8H, m) q, J=8.4 Hz), 5.72 (0.4H, d, J=11.1 Hz), 5.78 (0.6H, d. J=15.2 1363. The stereochemistry of the -CH=CH-bond was Hz), 6.71-748 (11H, m) mixture of E and Z. 1355. The stereochemistry of the -CH=CH-bond was mixture of E and Z. Example 154 Compound (154): Phenyl N-(4-hydroxyphenyl)-3- Example 151 (phenoxy)acrylimidate Compound (151): Ethyl 3-ethylthio-N-pheny 1364 To chloroform (80 ml) solution of phenyl N-(4- lacrylimidate methoxyphenyl)-3-(phenoxy)acrylimidate (2.4 g) was added 1356. To DMF (5 ml) solution of phenyl N-phenyl-3-phe dropwise with borone tribromide dichloromethane solution noxyacrylimidate (0.30 g) was added sodium salt of ethyl (1.0M: 14.0 ml) under ice-cooling and stirred for one hour at mercaptain (0.10 g) under ice-cooling, and stirred for three the same temperature and 2.5 hours at room temperature. hours at the same temperature. Ethyl acetate (80 ml) was Chloroform (200 ml) was added to the reaction solution and added to the reaction Solution, and it was successively washed it was successively washed with water and aqueous Saturated with water and aqueous Saturated Sodium chloride solution, Sodium chloride solution, dried over anhydrous magnesium dried over anhydrous magnesium sulfate and concentrated Sulfate and concentrated under reduced pressure. The residue under reduced pressure. DMF (5 ml) and sodium salt of ethyl was separated and purified by silica gel column chromatog mercaptain (0.1 g) were added to the residue, and stirred for raphy (hexane:ethyl acetate=3:1) to obtain phenyl N-(4-hy three hours at room temperature. Ethyl acetate (80 ml) was droxyphenyl)-3-(phenoxy)acrylimidate (0.46 g) as white added to the reaction Solution and it was successively washed crystal. with water and aqueous Saturated Sodium chloride solution, 1365 m.p.: 110° C. dried over anhydrous magnesium sulfate and concentrated 1366 'H-NMR (CDC1) & (ppm): 4.73 (1H, brs), 5.79 under reduced pressure. The residue was isolated and purified (1H, d J=11.8 Hz), 6.66-6.72 (4H, m), 7.06-7.39 (10H, m), by silica gel column chromatography (hexane:ethyl 7.79 (1H, d J=11.8 Hz). acetate=10:1) to obtain ethyl N-phenyl-3-(ethylthio) 1367. The stereochemistry of the -CH=CH-bond was acrylimidate (0.14 g) as yellow oil. H-NMR (CDC1) & E. (ppm): 1.24 (3H, t, J–7.3 Hz), 1.34 (3H, t, J–7.3 Hz), 2.65 (2H, q, J–7.3 Hz), 3.07 (2H, q, J=7.3 Hz), 6.01 (1H, d, J=15.6 Example 155 Hz), 6.78 (2H, d, J=7.6 Hz), 7.03-7.06 (1H, m), 7.23-7.31 Compound (155): Phenyl N-(4-acetoxyphenyl)-3- (3H, m). (phenoxy)acrylimidate 1357 The stereochemistry of the —CH=CH-bond was E. 1368 Potassium carbonate (0.075 g) and acetyl chloride (0.035 ml) were added to DMF (3 ml) solution of phenyl Example 152 N-(4-hydroxyphenyl)-3-(phenoxy)acrylimidate (0.15 g) at Compound (152): N-Methyl-N-phenyl-N'-phenyl-3- room temperature and stirred for two hours at the same tem (4-chlorophenylthio)acrylamidine perature and for three hours at 50° C. t-Butyl methyl ether (80 ml) was added to the reaction solution, and it was succes 1358 N-methyl-N-phenyl-N'-phenylpropynamidine sively washed with water and aqueous saturated Sodium chlo (0.23 g) was dissolved to chloroform (5 ml), chloroform (5 ride solution, dried over anhydrous magnesium Sulfate, con ml) solution of 4-chlorothiophenol (0.14 g) was added drop centrated under reduced pressure. The residue was separated wise under ice-cooling and stirred for 14 hours at room tem and purified by silica gel column chromatography (hexane: perature. The reaction Solution was concentrated under ethyl acetate=4:1) to obtain phenyl N-(4-acetoxyphenyl)-3- reduced pressure. The residue was purified by silica gel col (phenoxy)acrylimidate (0.11 g) as colorless oil. US 2011/0319437 A1 Dec. 29, 2011

1369 'H-NMR (CDC1) & (ppm): 2.27 (3H, s), 5.79 (1H, 1377 The stereochemistry of the —CH=CH-bond was d J=11.8 Hz), 6.78-6.80 (2H, m), 6.98-7.00 (2H, m), 7.06-7. E. 08 (2H, m), 7.15-7.23 (4H, m), 7.34-7.40 (4H, m), 7.82 (1H, dJ=11.8 Hz). Example 158 1370. The stereochemistry of the -CH=CH-bond was E. Compound (158): Phenyl N-(4-biphenyl)-3-(phe noxy)acrylimidate Example 156 1378 Phenyl N-(4-iodophenyl)-3-(phenoxy)acrylimidate Compound (156): Phenyl N-(4-ethynylphenyl)-3- (0.30 g), phenylboronic acid (0.091 g), bis(benzylideneac (phenoxy)acrylimidate etone)palladium(0) (0.015 g) and cesium carbonate (0.26 g) were suspended to THF (15 ml). Tri-t-butylphosphine (10 wt 1371 Phenyl N-(4-iodophenyl)-3-(phenoxy)acrylimidate % in hexane: 0.11 g) was added thereto and stirred for 16 (0.40 g), bis(acetonitrile) dichloro palladium (II) (0.016 g) hours at room temperature. The unsolved matter was filtered and copper iodide(I) (0.006 g) were suspended to dioxane (5 off, and the filtrate was concentrated under reduced pressure. ml). Diisopropylamine (0.090 ml), tri-t-butylphosphine (10 The residue was separated and purified by silica gel column wt % in hexane: 0.24 g) and trimethylsilyl acetylene (0.12 g) chromatography (hexane:ethyl acetate=20:1) to obtain phe were added thereto under ice-cooling, and stirred for eight nyl N-(4-biphenyl)-3-(phenoxy)acrylimidate (0.06 g) as light hours at room temperature.t-Butyl methyl ether (50 ml) was yellow crystal. added to the reaction Solution, and was successively washed 1379 'H-NMR (CDC1) & (ppm): 5.82 (1H, d J=12.1 Hz), with water and aqueous Saturated Sodium chloride solution, 6.88 (2H, dJ=8.2 Hz), 7.07 (2H, dJ=7.7 Hz), 7.13-7.43 (11H, dried over anhydrous magnesium sulfate and concentrated m), 7.50-7.52 (2H, m), 7.56-7.58 (2H, m), 7.83 (1H, dJ=12.1 under reduced pressure. The residue was separated and puri Hz). fied by silica gel column chromatography (hexane:ethyl 1380 The stereochemistry of the —CH=CH-bond was acetate-4:1) to obtain white crystal (0.15g). E 1372 The above-mentioned crystal was dissolved to 1381 Compound (159) was synthesized in a similar man methanol (5 ml), potassium carbonate (0.010 g) was added ner as the Example 158. and stirred for four hours at room temperature. The reaction Solution was concentrated under reduced pressure. The resi due was separated and purified by silica gel column chroma Example 159 tography (hexane:ethyl acetate=5:1) to obtain phenyl N-(4- Compound (159): Phenyl 3-phenoxy-N-(4-(3-thie ethynylphenyl)-3-(phenoxy)acrylimidate (0.12 g) as yellow nyl)phenyl)acrylimidate solid. 1373 'H-NMR (CDC1) & (ppm): 3.02(1H, s), 5.68 (1H, 1382 m.p.: 117° C. d J=11.8 Hz), 6.75 (2H, d J=8.2 Hz), 7.06 (2H, d J=7.7 Hz), 1383 'H-NMR (CDC1) & (ppm): 5.80 (1H, d J=11.8 Hz), 7.14-7.22 (4H, m), 7.34-7.41 (6H, m), 7.82 (1H, d J=11.8 6.84 (2H, d J=8.2 Hz), 7.07 (2H, d J=8.0 Hz), 7.13-7.23 (4H, Hz). m), 7.33-742 (7H, m), 7.50-7.52 (2H, m), 7.82 (1H, dJ=11.8 1374 The stereochemistry of the —CH=CH-bond was Hz). E. 1384) The stereochemistry of the —CH=CH-bond was E. Example 157 Example 160 Compound (157): Phenyl N-(4-vinylphenyl)-3-(phe noxy)acrylimidate Compound (160): Phenyl N-(4-methylsulfinylphe nyl)-3-(phenoxy)acrylimidate 1375 Phenyl N-(4-iodophenyl)-3-(phenoxy)acrylimidate (0.50g), bis(benzylideneacetone)palladium (0) (0.023 g) and Compound (161): Phenyl N-(4-methylsulfonylphe cesium carbonate (0.82 g) were suspended to dioxane (15 nyl)-3-(phenoxy)acrylimidate ml). Tri-t-butylphosphine (10 wt % in hexane: 0.24 g) and tributyl (vinyl) tin (0.44 g) were added thereto and it was 1385 Phenyl N-(4-methylthiophenyl)-3-(phenoxy) stirred for four hours at room temperature and 60°C. for five acrylimidate (0.50 g) was dissolved to chloroform (15 ml), hours. The unsolved matter was filtered off, and the filtrate then chloroform (10 ml) solution of m-chloroperbenzoic acid was concentrated under reduced pressure. The residue was (0.55g) was added dropwise under ice-cooling and stirred for separated and purified by silica gel column chromatography five hours at room temperature. Chloroform (50 ml) was (hexane:ethyl acetate=30:1) to obtain phenyl N-(4-vinylphe added thereto, and it was successively washed with 1N aque nyl)-3-(phenoxy)acrylimidate (0.29 g) as yellow oil. ous sodium hydroxide solution, water and aqueous Saturated 1376) "H-NMR (CDC1,) & (ppm): 5.15 (1H, dJ=11.6 Hz), Sodium chloride solution, dried over anhydrous magnesium 5.65 (1H, d J=18.4 Hz), 5.76 (1H, d J=12.1 Hz), 6.63-6.70 Sulfate, concentrated under reduced pressure. The residue (1H, m), 6.76 (2H, d J=8.2 Hz), 7.06 (2H, d J=7.7 Hz), was separated and purified by silica gel column chromatog 7.13-7.22 (4H, m), 7.31-741 (6H, m), 7.80 (1H, d J=12.1 raphy (hexane:ethyl acetate=1:1) to obtain phenyl N-(4-me Hz). thylsulfinylphenyl)-3-(phenoxy)acrylimidate (0.30 g) as yel US 2011/0319437 A1 Dec. 29, 2011 66 low oil and phenyl N-(4-methylsulfonylphenyl)-3-(phenoxy) 1399 The stereochemistry of the —CH=CH-bond was acrylimidate (0.18 g) as yellow oil. Z. Compound (160): Example 165 1386 H-NMR (CDC1) & (ppm): 2.70 (3H, s), 5.65 (1H, Compound (166): Benzyl 3-(4-fluorophenylthio)-N- d J=11.8 Hz), 6.94 (2H, d J=8.2 Hz), 7.06-7.08 (2H, m), (phenyl)thioacrylimidate 7.15-7.23 (4H, m), 7.34-7.42 (4H, m), 7.56 (2H, d J=8.2 Hz), 1400 'H-NMR (CDC1) & (ppm): 4.30 (2H, s), 5.94 (1H, 7.85 (1H, d J=11.8 Hz). d, J=15.6 Hz), 6.67-6.73 (1H, m), 6.93-7.09 (3H, m), 720-7. 1387. The stereochemistry of the -CH=CH-bond was 42 (11 H. m). E. 1401 The stereochemistry of the —CH=CH-bond was Compound (161): E. 1388. 'H-NMR (CDC1) & (ppm): 3.30 (3H, s), 5.59 (1H, Example 166 d J=11.8 Hz), 6.95 (2H, d J=8.2 Hz), 7.06-7.08 (2H, m), Compound (167): Benzyl 3-(4-chlorophenylthio)-N- 7.17-721 (4H, m), 7.35-7.40 (4H, m), 7.83 (2H, d J=8.2 Hz), (phenyl)thioacrylimidate 7.87 (1H, d J=11.8 Hz). 1389. The stereochemistry of the -CH=CH-bond was 1402 'H-NMR (CDC1) & (ppm): 4.31 (2H, s), 6.03 (1H, E. d, J=15.5 Hz), 6.72 (2H, d, J=7.5 Hz), 7.04-7.10 (1H, m), 7.21-7.41 (12H, m). Example 161 1403. The stereochemistry of the —CH=CH-bond was Compound (162): Methyl N-phenyl-3-(4-methylphe E. nylthio)thioacrylimidate Example 167 1390 Methyl N-phenylpropynthioimidate (0.30 g) was Compound (168): Benzyl 3-(3-methylphenylthio)-N- dissolved to chloroform (5 ml), 4-methylthiophenol (0.19 g) (phenyl)thioacrylimidate was added dropwise under ice-cooling and stirred for 15 hours at room temperature. The reaction Solution was con 1404 'H-NMR (CDC1) & (ppm): 2.30 (3H, s), 4.31 (2H, centrated under reduced pressure. The residue was purified by s), 6.06 (1H, d, J=15.3 Hz), 6.73 (2H, d, J=8.2 Hz), 7.00-7.42 silica gel column chromatography (hexane:ethyl acetate-15: (13H, m). 1) to obtain methyl N-phenyl-3-(4-methylphenylthio)thio 1405. The stereochemistry of the -CH=CH-bond was acrylimidate (0.20 g) as light yellow oil. E. 1391 H-NMR (CDC1) & (ppm): 2.33 (3H, s), 2.43 (3H, s), 5.99 (1H, d, J=15.1 Hz), 6.68-6.75 (2H, m), 7.00-7.35 (8H, Example 168 m). Compound (169): Benzyl N-phenyl-3-(3-trifluorom 1392 The stereochemistry of the —CH=CH-bond was ethylphenylthio)thioacrylimidate E. 1393 Compounds (163) to (169) were synthesized in a 1406 H-NMR (CDC1) & (ppm): 4.33 (2H, s), 6.09 (1H, similar manner as the Example 161. d, J=15.6 Hz), 6.73 (2H, d, J=8.2 Hz), 7.02-7.10 (1H, deft), 7.21-7.63 (12H, m). Example 162 1407. The stereochemistry of the -CH=CH-bond was Compound (163): Methyl N-phenyl-3-(phenylthio) E. thioacrylimidate 1408 Compounds (170) to (173) were synthesized in a similar manner as the Example 37. 1394 'H-NMR (CDC1) & (ppm): 2.44 (3H, s), 6.09 (1H, d, J=15.6 Hz), 6.73 (2H, d, J=7.3 Hz), 7.00-7.39 (9H, m). Example 169 1395 The stereochemistry of the -CH=CH-bond was Compound (170): 4-Methylthiophenyl E. 1409 N-4-(1-methylethyl)phenyl-3-(phenylthio) Example 163 acrylimidate Compound (164): Methyl 3-(4-chlorophenylthio)-N- 1410 "H-NMR (CDC1) & (ppm): 1.22 (6H, d, J=6.8 Hz), (phenyl)thioacrylimidate 2.45 (3H, s), 2.84 (1H, sept J=6.8 Hz), 5.90 (1H, d. J=15.2 Hz), 6.64 (2H, d, J=8.2 Hz), 7.05-7.41 (11H, m), 7.66 (1H, d, 1396 H-NMR (CDC1) & (ppm): 2.44 (3H, s), 6.04 (1H, J=15.2 Hz). d, J=16.1 Hz), 6.71 (2H, d, J=7.7 Hz), 7.06(1H, br), 7.22-7.31 1411. The stereochemistry of the —CH=CH-bond was (7H, m). E. 1397) The stereochemistry of the —CH=CH-bond was E. Example 170 Compound (171): 4-Methylsulfonylphenyl N-4-(1- Example 164 methylethyl)phenyl-3-(phenylthio)acrylimidate Compound (165): Methyl 3-(4-chlorophenylthio)-N- (phenyl)thioacrylimidate 1412 H-NMR (CDC1) & (ppm): 1.22 (6H, d, J–7.0 Hz), 2.85 (1H, sept J=70 Hz), 3.04 (3H, s), 5.90 (1H, d, J=15.0 1398 H-NMR (CDC1) & (ppm): 2.41 (3H, brs), 6.40 Hz), 6.66 (2H, d, J=8.5 Hz), 7.08-7.45 (9H, m), 7.69 (1H, d, (1H, br), 6.90-7.48 (10H, m). J=15.0 Hz, CH), 7.94 (2H, d, J=8.7 Hz). US 2011/0319437 A1 Dec. 29, 2011 67

1413 The stereochemistry of the —CH=CH-bond was 1425 The stereochemistry of the —CH=CH-bond was E. E.

Example 171 Example 176 Compound (172): 4-Cyclohexylphenyl N-4-(1-me Compound (177): 4-(1,1-Dimethylethyl)phenyl thylethyl)phenyl-3-(phenylthio)acrylimidate N-phenyl-3-(phenylthio)thioacrylimidate 1414 'H-NMR (CDC1) & (ppm): 1.21 (6H, d. J=6.8 Hz), 1.26-1.40 (6H, m), 1.84 (4H, m), 2.47 (1H, m), 2.84 (1H, sept 1426 N-phenyl-3-(phenylthio)acrylamide (0.77 g) was J=6.8 Hz), 5.91 (1H, d, J=15.2 Hz), 6.64 (2H, d, J=8.2 Hz), suspended to toluene (15 ml), then thionyl chloride (0.52 ml) 7.04-7.45 (11H, m), 7.65 (1H, d, J=15.2 Hz, CH). and one drop of DMF were added thereto at room tempera 1415. The stereochemistry of the —CH=CH-bond was ture. The mixture was stirred on 60° C. oil bath for one hour. E. The reaction mixture was concentrated under reduced pres sure. The residue was dissolved to THF (15 ml). 1427 Sodium hydride (55% in oil: 0.25 g) was suspended Example 172 to THF (5 ml) under ice-cooling, and 4-(tert-butyl)thiophenol Compound (173): 3-Biphenyl N-4-(1-methylethyl) (0.57 ml) was added thereto under ice-cooling. The suspen phenyl)-3-(phenylthio)acrylimidate sion was added to the above THF solution of the residue under ice-cooling, and stirred at the same temperature for 15 min 1416) 'H-NMR (CDC1) & (ppm): 1.21 (6H, d. J=6.8 Hz), utes. Then methyliodide (0.1 ml) was added thereto. Aqueous 2.84 (1H, sept J=6.8 Hz), 5.94 (1H, d, J=15.1 Hz), 6.67 (2H, saturated sodium chloride solution (20 ml) and water (10 ml) d, J=8.0 Hz), 7.05-7.59 (16H, m), 7.70 (1H, d, J=15.1 Hz). was added to the reaction mixture and it was extracted with 1417. The stereochemistry of the —CH=CH-bond was ethyl acetate (20 ml) twice. The organic layers were com E. bined and washed with aqueous Saturated sodium chloride 1418 Compound (174) was synthesized in a similar man solution (20 ml), dried over anhydrous sodium sulfate, fil ner as the Example 161. tered offinorganic salt, concentrated under reduced pressure to obtain brown oil (1.36 g). It was subjected to silica gel column chromatography (hexane:ethyl acetate-20:1) to Example 173 obtain light yellow oil, and it was purified by medium pres Sure preparative high performance liquid chromatography Compound (174): 1-Methylethyl N-phenyl-3-(phe (hexane:ethyl acetate=99: 1) to obtain 4-(1,1-dimethylethyl) nylthio)thioacrylimidate phenyl N-phenyl-3-(phenylthio)thioacrylimidate (0.20 g). 1419 'H-NMR (CDC1) & (ppm): 1.38 (6H, d, J=7.8 Hz), 1428 H-NMR (CDC1) & (ppm): 1.33 (9H, s), 5.83 (1H, 3.82-3.94 (1H, m), 6.06 (1H, d, J=15.6 Hz), 6.73 (2H, d, J=8.0 d J=15.0 Hz), 6.90-7.58 (15H, m). Hz), 7.03 (1H, t, J–74 Hz), 7.22-7.40 (8H, m). 1429. The stereochemistry of the —CH=CH-bond was 1420. The stereochemistry of the —CH=CH-bond was E E. 1430 Compounds (178) and (179) were synthesized in a 1421 Compounds (175) and (176) were synthesized in a similar manner as the Example 176. similar manner as the Example 37. Example 177 Example 174 Compound (178): 2-Naphtyl N-4-(1-methylethyl) Compound (175): Phenyl N-(4-cyclohexylphenyl)-3- phenyl-3-(phenylthio)thioacrylimidate (phenylthio)acrylimidate 1422 H-NMR (CDC1) & (ppm): 1.29-1.45 (4H, m), 1431 H-NMR (CDC1) & (ppm): 1.24 (6H, d J–7.0 Hz), 1.68-1.91 (6H, m), 2.38-2.49 (1H, m), 5.81 (0.21H, d J=15.0 2.85-2.92 (1H, m), 5.55 (1H, d J=15.0 Hz), 6.62-8.05 (17H, Hz), 5.93 (0.75H, d, J=15.2 Hz), 6.13 (0.04H, d, J=9.9 Hz), m). 6.64 (1H, d, J=8.2 Hz), 7.01-7.56 (13.04H, m), 7.67 (0.75H, 1432 The stereochemistry of the —CH=CH-bond was d J=15.2 Hz), 8.00 (0.21H, d J=15.0 Hz) E. 1423. The stereochemistry of the —CH=CH-bond was mixture of E and Z. Example 178 Compound (179): 2-Naphtyl N-4-(1-methylethyl) Example 175 phenyl-3-(phenylthio)thioacrylimidate Compound (176): Phenyl N-(4-cyclohexylthiophe nyl)-3-phenoxyacrylimidate 1433 'H-NMR (CDC1) & (ppm): 1.28 (6H, d J=7.0 Hz), 2.90-2.97 (1H, m), 5.83 (1H, dJ=10.1 Hz), 6.78 (1H, d J=9.9 1424 'H-NMR (CDC1) & (ppm): 0.87-0.90 (2H, m), Hz), 7.07 (2H, d J=8.2 Hz), 7.25-7.32 (5H, m), 7.43 (2H, d 1.23-1.33 (4H, m), 1.74-1.76 (2H, m), 1.92-1.94 (2H, m), J=6.7 Hz), 7.53 (3H, d J=7.2 Hz), 7.82 (3H, dJ=8.5 Hz), 8.04 2.98-3.00 (1H, m), 5.74 (1H, d, J=12.0 Hz), 6.73 (2H, d, J=8.3 (1H, s). Hz), 7.07 (2H, d, J=8.0 Hz), 7.13-7.22 (4H, m), 7.33-7.40 1434 The stereochemistry of the —CH=CH-bond was (6H, m), 7.82 (1H, d. J=12.0 HZ, CH). Z.

US 2011/0319437 A1 Dec. 29, 2011 69

1460 Compound (191) was synthesized in a similar man 1474 Compounds (196) and (197) were synthesized in a ner as the Example 161. similar manner as the Example 37. Example 190 Example 195 Compound (191): 2-Propynyl N-phenyl-3-(phe Compound (196): Phenyl 3-phenoxy-N-(4-piperidi nylthio)thioacrylimidate nophenyl)acrylimidate 1461 H-NMR (CDC1) & (ppm): 2.19 (1H, t, J=2.5 Hz), 3.86 (2H, d. J=2.7 Hz), 6.10 (1H, d, J=15.4 Hz), 6.74 (2H, d, 1475 'H-NMR (CDC1,) & (ppm): 1.53-1.57 (2H, m), J=7.5 Hz), 7.03-7.60 (9H, m). 1.68-1.73 (4H, m), 3.05-3.08 (4H, m), 5.84 (1H, d, J=12.1 1462. The stereochemistry of the —CH=CH-bond was Hz), 6.71-6.73 (2H, m), 6.86-6.88 (2H, m), 705-7.07 (2H, E. m), 7.14-7.23 (4H, m), 7.33-7.39 (4H, m), 7.78 (1H, d, J–12.1 1463 Compounds (192) and (193) were synthesized in a Hz). similar manner as the Example 37. 1476 The stereochemistry of the —CH=CH-bond was E. Example 191 Example 196 Compound (192): 2,5-Dichlorophenyl N-phenyl-3- phenoxyacrylimidate Compound (197): 2,5-Dichlorophenyl N-4-(1-meth 1464. H-NMR (CDC1) & (ppm): 5.71 (1H, d. J=12.0Hz), ylethyl)phenyl-3-phenoxyacrylimidate 6.80 (2H, d, J=7.8 Hz), 6.90-7.43 (11H, m), 7.85 (1H, d, J=12.0 Hz). 1477 'H-NMR (CDC1) & (ppm): 1.21 (6H, d, J–7.0 Hz), 1465. The stereochemistry of the —CH=CH-bond was 2.85 (1H, sept J=7.0 Hz), 5.78 (1H, d, J=11.8 Hz), 6.73 (2H, E. d, J=8.2 Hz), 7.05-7.37 (10H, m), 7.84 (1H, d, J=11.8 Hz). 1478. The stereochemistry of the -CH=CH-bond was E Example 192 1479 Compounds (198) and (199) were synthesized in a Compound (193): 2-Naphtyl N-phenyl-3-phenoxy similar manner as the Example 161. acrylimidate Example 197 1466 H-NMR (CDC1) & (ppm): 5.79 (1H, d. J=12.0Hz), 6.82 (2H, d, J=7.3 Hz), 6.97-7.90 (16H, m). Compound (198): 1-Methylethyl N-phenyl-3-(phe 1467. The stereochemistry of the —CH=CH-bond was noxy)thioacrylimidate E. 1468 Compound (194) was synthesized in a similar man 1480 'H-NMR (CDC1) & (ppm): 1.40 (6H, d, J=7.3 Hz), ner as the Example 161. 3.90-402 (1H, m), 5.94 (1H, d =12.6 Hz), 6.95-7.40 (10H, m), 7.52 (1H, d, J=12.5 Hz). Example 193 1481. The stereochemistry of the —CH=CH-bond was E. Compound (194): 1-Phenethyl N-phenyl-3-(phe nylthio)thioacrylimidate Example 198 1469 'H-NMR (CDC1) & (ppm): 1.74 (3H, d, J=7.7 Hz), 4.96-5.06(1H, m), 6.04 (1H, d, J=15.7 Hz), 6.70 (2H, d, J–7.5 Compound (199): Benzyl 3-(4-methylbenzylthio)-N- Hz), 7.00-7.46 (14H, m). (phenyl)thioacrylimidate 1470. The stereochemistry of the -CH=CH-bond was E. 1482 'H-NMR (CDC1) & (ppm): 2.32 (3H, s), 3.79 (2H, 1471 Compound (195) was synthesized in a similar man s), 4.29 (2H, s), 6.07 (1H, d, J=15.4 Hz), 6.78 (2H, d, J–7.3 ner as the Example 100. Hz), 7.00-7.40 (13H, m). 1483. The stereochemistry of the —CH=CH-bond was E Example 194 1484 Compounds (200) to (204) were synthesized in a Compound (195): Phenyl 3-(1-naphthylthio)-N-phe similar manner as the Example 37. nylacrylimidate Example 199 1472 H-NMR (CDC1) & (ppm): 5.58 (1H, d, J=15.0 Hz), 6.52 (2H, d, J–7.2 Hz), 6.85-6.89 (1H, m), 6.99-703 (2H, m), Compound (200): 2,3-Dichlorophenyl N-4-(1-meth 7.12-7.17 (3H, m), 7.32-7.42 (3H, m), 7.54-7.62 (2H, m), ylethyl)phenyl-3-phenoxyacrylimidate 7.66 (1H, d, J=15.0 Hz), 7.71-7.73 (1H, m), 7.83-7.88 (2H, m), 8.27-8.29 (1H, m). 1485 H-NMR (CDC1) & (ppm): 1.21 (6H, d, J=7.4 Hz), 1473. The stereochemistry of the -CH=CH-bond was 2.85 (1H, sept J=7.4 Hz), 5.78 (1H, d, J=12.0 Hz), 6.72 (2H, E. d, J=8.3 Hz), 7.05-7.38 (10H, m), 7.85 (1H, d, J=12.0 Hz). US 2011/0319437 A1 Dec. 29, 2011 70

1486 The stereochemistry of the —CH=CH-bond was 1502 Compound (207) was synthesized in a similar man E. ner as the Example 37. Example 200 Example 206 Compound (201): 3,5-Dichlorophenyl N-4-(1-meth ylethyl)phenyl-3-phenoxyacrylimidate Compound (207): Phenyl N-(4-trifluoromethoxyphe nyl)-3-phenoxyacrylimidate 1487 'H-NMR (CDC1) & (ppm): 1.23 (6H, d. J=6.8 Hz), 2.87 (1H, sept J=6.8 Hz), 5.78 (1H, d, J=12.0 Hz), 6.74 (2H, 1503) 'H-NMR (CDC1)8(ppm):5.69(1H,d, J=11.8 Hz), d, J=8.3 Hz), 7.03-7.37 (10H, m), 7.73 (1H, d, J=12.0 Hz). 6.79 (2H, d, J=8.7 Hz), 7.06-7.22 (8H, m), 7.34-7.41 (4H, m), 1488. The stereochemistry of the —CH=CH-bond was 7.84 (1H, d, J=11.8 Hz). E. 1504) The stereochemistry of the -CH=CH-bond was E. Example 201 1505 Compound (208) was synthesized in a similar man Compound (202): 2,4-Dichlorophenyl N-4-(1-meth ner as the Example 161. ylethyl)phenyl-3-phenoxyacrylimidate 1489 H-NMR (CDC1) & (ppm): 1.21 (6H, d. J=6.8 Hz), Example 207 2.85 (1H, sept J=6.8 Hz), 5.77 (1H, d, J=12.0 Hz), 6.71 (2H, d, J=8.3 Hz), 7.05-7.43 (10H, m), 7.84 (1H, d, J=12.0 Hz). Compound (208): Cyclohexyl N-phenyl-3- 1490. The stereochemistry of the -CH=CH-bond was (phenylthio9thioacrylimidate E. 1506) H-NMR (CDC1) & (ppm): 1.26-2.15 (8H, m), 3.22 Example 202 (2H, brs), 3.95 (1H, Br), 6.42 (1H, d, J=10.1 Hz), 6.90-7.55 (11H, m). Compound (203): 3-Methylphenyl N-(3,4-dimeth 1507. The stereochemistry of the -CH=CH-bond was ylphenyl)-3-phenylthioacrylimidate Z. 1491 'H-NMR (CDC1) & (ppm): 2.19 (6H, s), 2.34 (3H, 1508 Compound (209) was synthesized in a similar man s), 5.96 (1H, d, J=15.0 Hz), 6.47-6.53 (2H, m), 6.95-7.43 ner as the Example 37. (10H, m), 7.65 (1H, d, J=15.0 Hz, CH). 1492. The stereochemistry of the —CH=CH-bond was Example 208 E. Compound (209): 3-Methylphenyl N-(3,4-dimeth Example 203 ylphenyl)-3-phenoxyacrylimidate Compound (204): Phenyl N-(4-benzylphenyl)-3- phenoxyacrylimidate 1509 H-NMR (CDC1) & (ppm): 2.20 (3H, s), 2.21 (3H, s), 2.36 (3H, s), 5.80 (1H, d, J=11.8 Hz), 6.54-6.60 (2H, m), 1493) 'H-NMR (CDC1) & (ppm): 3.93 (2H, s), 5.78 (1H, 6.96-7.37 (10H, m), 7.76 (1H, d, J=12.1 Hz). d, J=12.1 Hz), 6.72 (2H, d, J=8.5 Hz), 7.05-7.09 (4H, m), 1510. The stereochemistry of the -CH=CH-bond was 7.11-7.40 (13H, m), 7.79 (1H, d, J=12.1 Hz). E. 1494 The stereochemistry of the —CH=CH-bond was 1511 Compound (210) was synthesized in a similar man E. ner as the Example 100. 1495 Compound (205) was synthesized in a similar man ner as the Example 161. Example 209 Example 204 Compound (210): 3-Methylphenyl N-(3,4-dimeth Compound (205): Benzyl N-phenyl-3-(phenoxy) ylphenyl)-3-benzyloxyacrylimidate thioacrylimidate 1496 'H-NMR (CDC1) & (ppm): 4.36 (2H, s), 5.96 (1H, 1512) 'H-NMR (CDC1) & (ppm): 2.19 (6H, s), 2.35 (3H, d, J=12.3 Hz), 6.77-7.54 (16H, m). s), 4.80 (2H, s), 5.42(1H, d, J=12.3 Hz), 6.52-7.21 (12H, m), 1497. The stereochemistry of the -CH=CH-bond was 7.62 (1H, d, J=12.3 Hz). E. 1513. The stereochemistry of the -CH=CH-bond was 1498 Compound (206) was synthesized in a similar man E. ner as the Example 99. 1514 Compounds (211) to (234) were synthesized in a similar manner as the Example 161. Example 205 Compound (206): Phenyl N-phenyl-3-(phenylsulfo Example 210 nyl)thioacrylimidate Compound (211): Benzyl 3-(2-fluorophenylthio)-N- 1499 m.p.: 69-70° C. phenyl-thioacrylimidate 1500I 'H-NMR (CDC1) & (ppm): 6.86-7.74 (m) 1501. The stereochemistry of the -CH=CH-bond was 1515) 'H-NMR (CDC1) & (ppm): 4.30 (2H, s), 6.00 (1H, mixture of E and Z. d J=15.7 Hz), 6.73 (2H, d J=7.3 Hz), 7.02-7.39 (13H, m).

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1564 The stereochemistry of the —CH=CH-bond was 1576 'H-NMR (CDC1) & (ppm): 5.21 (2H, s), 5.49 (1H, E. d, J=15.0 Hz), 6.99 (1H, d, J=15.0 Hz), 7.14-7.18 (2H, m), 7.21-7.39 (13H, m). Example 233 1577. The stereochemistry of the -CH=CH-bond was Compound (256): Benzyl N-phenyl-3-(2-pyrim E idylthio)-thioacrylimidate 1578 Compound (262) was synthesized in a similar man ner as the Example 36. 1565. H-NMR (CDC1) & (ppm): 4.36 (2H, s), 6.44 (1H, d J=16.4 Hz), 6.81 (2H, d J=7.3 Hz), 7.05-7.12 (2H, m), Example 238 7.24-7.35 (5H, m), 7.44 (2H, dJ=7.1 Hz), 8.30 (1H, d J=16.4 Hz), 8.57 (2H, d J=5.1 Hz). Compound (262): Phenyl N-(N-Methyl-N'-pheny 1566. The stereochemistry of the -CH=CH-bond was lamino)-3-(phenylthio)thioacrylimidate E. 1579 'H-NMR (CDC1) & (ppm): 3.17 (3H, s), 5.53 (1H, Example 234 d, J=14.7 Hz), 6.90-6.96 (3H, m), 7.20-7.42 (13H, m). 1580. The stereochemistry of the -CH=CH-bond was Compound (258): Benzyl 3-(3,4-dichlorophe E nylthio)-N-phenyl-thioacrylimidate 1581 Compounds (263) to (265) were synthesized in a 1567 'H-NMR (CDC1) & (ppm): 4.32 (2H, s), 6.06 (1H, similar manner as the Example 176. d, J=15.5 Hz), 6.73 (2H, d, J=7.5 Hz), 7.10-7.43 (12H, m). 1568. The stereochemistry of the -CH=CH-bond was Example 239 E. 1569 Compound (259) was synthesized in a similar man Compound (263): Phenyl N-(4-fluorophenyl)-3- ner as the Example 176. (phenylthio)thioacrylimidate Example 235 1582 'H-NMR (CDC1,) & (ppm): 5.80 (1H, dJ=102 Hz), 6.84 (1H, d J=10.2 Hz), 7.05-7.11 (4H, m), 7.25-7.51 (10H, Compound (259): 4-(1-Methylethyl)phenyl N-(4- m). methylphenyl)-3-(phenylthio)thioacrylimidate 1583 The stereochemistry of the —CH=CH-bond was 1570 'H-NMR (CDC1) & (ppm): 1.23 (6H, d J–7.0 Hz), Z. 2.29 (3H, s), 2.82 (1H, sept. J=7.0 Hz), 5.93 (1H, d J=15.0 Hz), 6.63 (2H, dJ=7.8 Hz), 7.02 (2H, d J=8.0 Hz), 7.11 (2H, Example 240 d J=8.3 Hz), 7.20-7.42 (7H, m), 7.66 (1H, d J=15.0 Hz). 1571. The stereochemistry of the -CH=CH-bond was Compound (264): Phenyl N-(4-fluorophenyl)-3- E. (phenylthio)thioacrylimidate 1572 Compound (260) was synthesized in a similar man 1584 H-NMR (CDC1) & (ppm): 5.67 (0.77H, d J=14.6 ner as the Example 161. Hz), 5.80 (0.08H, d J=10.0 Hz), 5.99 (0.15H, d J=15.4 Hz), 6.62 (0.3H, brm), 6.82-6.61 (1.7H, m), 6.99-7.09 (2H, m), Example 236 7.25-7.57 (11H, m). Compound (260): Benzyl N-(4-methylphenyl)-3- 1585. The stereochemistry of the -CH=CH-bond was (phenylthio)thioacrylimidate mixture of E and Z. 1573 'H-NMR (CDC1) & (ppm): 2.32 (3H, s), 4.30 (2H, s), 6.13 (1H, d, J=15.7 Hz), 6.65 (2H, d, J=8.0 Hz), 7.21-7.39 Example 241 (13H, m). Compound (265): 1,1-Dimethylethyl N-(4-meth 1574. The stereochemistry of the -CH=CH-bond was ylphenyl)-3-(phenylthio)thioacrylimidate E. 1586 'H-NMR (CDC1,) & (ppm): 1.38 (2.1H, s), 1.56 Example 237 (6.9H, s), 2.31 (0.7H, s), 2.32 (2.3H, s), 6.07 (0.77H, dJ=15.5 Compound (261): Phenyl N-benzyloxy-3-(phe Hz), 6.15 (0.23H, d J=15.7 Hz), 6.64 (d J=8.5 Hz), 6.67 (d nylthio)thioacrylimidate J=8.2 Hz) total 2H, 7.06-7.09 (2H, m), 727-7.38 (6H, m). 1587. The stereochemistry of the -CH=CH-bond was 1575 Sodium salt of thiophenol (0.14 g) was added to E. ethanol (5 ml) solution of N-benzyloxy-3-phenylthio 1588 Compounds (266) and (267) were synthesized in a acrylimidoyl bromide (0.30 g) at room temperature, then it similar manner as the Example 161. was heat refluxing for three hours. It was cooled, and chloro form (50 ml) was added to the reaction mixture. It was suc Example 242 cessively washed with 1N aqueous sodium hydroxide solu tion, pure water, aqueous Saturated Sodium chloride solution. Compound (266): Ethyl N-(4-methylphenyl)-3-(phe The organic layer was dried over anhydrous magnesium Sul nylthio)thioacrylimidate fate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl 1589 H-NMR (CDC1) & (ppm): 1.33 (3H, t J=7.4 Hz), acetate=20:1) to obtain phenyl N-benzyloxy-3-(phenylthio) 2.32 (3H, s), 2.89 (2H, sept), 6.13 (1H, d, J=15.5 Hz), 6.63 thioacrylimidate (0.14 g) as colorless oil. (2H, d, J=8.2 Hz), 7.05-7.38 (8H, m).

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1701 The stereochemistry of the —CH=CH-bond was 1714 Compound (325) was synthesized in a similar man E. ner as the Example 37. Example 296 Example 301 Compound (320): 3-Methylphenyl N-(3,4-dimeth Compound (325): Phenyl N-(3-biphenyl)-3-phe ylphenyl)-3-(4-methoxybenzyloxy)acrylimidate noxyacrylimidate 1702 'H-NMR (CDC1) & (ppm): 2.19 (6H, s), 2.35 (3H, 1715) 'H-NMR (CDC1) & (ppm): 5.70 (1H, d, J=11.8 Hz), s), 3.81 (3H, s), 4.74 (2 H, s), 5.39 (1H, d J=12.4 Hz), 6.50 6.80-7.78 (19H, m), 7.85 (1H, d, J=11.8 Hz). (1H, dJ=7.8 Hz), 6.56(1H, brs), 6.87-6.89 (2H, m), 6.95-7.00 1716. The stereochemistry of the -CH=CH-bond was (4H, m), 7.20-7.23 (3H, m), 7.60 (1H, d J=12.4 Hz). E. 1703. The stereochemistry of the -CH=CH-bond was E Example 302 1704 Compounds (321) to (324) were synthesized in a Compound (326): Phenyl N-phenoxy-3-(phenylthio) similar manner as the Example 161. thioacrylimidate Example 297 1717 N-phenoxy-3-(phenylthio)acrylamide (0.50 g) was Suspended to toluene (5 ml), then phosphorus pentachloride Compound (321): 2-Methylpropyl (0.42 g) was added thereto under ice-cooling and stirred at N-(4-methylphenyl)-3-(phenylthio)thioacrylimi same temperature for 2.5 hours. The reaction mixture was 1705 concentrated under reduced pressure. The residue was dis date solved to ethanol (15 ml). Sodium salt of thiophenol (0.73 g) 1706 H-NMR (CDC1) & (ppm): 1.01 (6H, d, J=6.5 Hz), was added to the solution underice-cooling and heatrefluxing 1.93 (1H, sept. J=6.7 Hz), 2.31 (3H, s), 2.99 (2H, d, J=6.8 Hz), for 2.5 hours. t-Butyl methyl ether (100 ml) was added to the 6.12 (1H, d, J=15.5 Hz), 6.62 (2H, d, J=8.0 Hz), 7.06 (2H, d, reaction mixture, washed Successively with 1N aqueous J=8.0 Hz), 7.29-7.39 (6H, m). Sodium hydroxide solution, water and aqueous saturated 1707. The stereochemistry of the -CH=CH-bond was Sodium chloride solution, dried over anhydrous Sodium Sul E. fate, filtered off inorganic salt and concentrated under reduced pressure. The residue was purified by medium pres Example 298 Sure preparative high performance liquid chromatography (hexane:ethyl acetate=30:1) to obtain phenyl N-(phenoxy)- Compound (322): 2-Methylpropyl N-(4-methylphe 3-(phenylthio)thioacrylimidate (0.14 g) as yellow oil. nyl)-3-(phenylthio)thioacrylimidate 1718 H-NMR (CDC1)8(ppm):5.45(1H,d, J=15.0Hz), 7.00-7.04 (1H, m), 7.18-7.46 (15H, m). 1708 H-NMR (CDC1) & (ppm): 0.97 (6H, brs), 1.57 1719. The stereochemistry of the -CH=CH-bond was (2H, s), 2.34 (3H, s), 2.77 (1H, brs), 6.38 (1H, d. J=9.7 Hz), E. 6.91-749 (10H, m). 1720 Compound (327) was synthesized in a similar man 1709. The stereochemistry of the -CH=CH-bond was ner as the Example 302. Z. Example 303 Example 299 Compound (327): Phenyl N-(phenylamino)-3-(phe Compound (323): Cyclohexyl N-phenyl-3-(cyclo nylthio)thioacrylimidate hexylthio)thioacrylimidate 1721 'H-NMR (CDC1,) 8 (ppm): 6.07 (0.41H, d, J=9.0 1710 'H-NMR (CDC1) & (ppm): 1.23-2.10 (20H, m), Hz), 6.55 (0.41H, d, J=9.0 Hz), 6.68 (0.59H, d, J=16.3 Hz), 2.84-2.89 (1H, m), 3.76-3.81 (1H, m), 6.03 (1H, d. J=15.7 6.88-6.94 (1H, m), 7.00 (0.59H, d, J=16.3 Hz), 7.03-7.07 (1H, Hz), 6.75-7.29 (6H, m). m), 7.19-7.37 (12H, m) 7.52-7.54 (1H, m), 8.68 (0.41H, brs, 1711. The stereochemistry of the -CH=CH-bond was NH), 8.74 (0.59H, brs, NH). E. 1722. The stereochemistry of the —CH=CH-bond was mixture of E and Z. Example 300 1723 Compounds (328) to (330) were synthesized in a similar manner as the Example 176. Compound (324): 1-Methylpropyl N-(4-methylphe nyl)-3-(phenylthio) thioacrylimidate Example 304 1712 H-NMR (CDC1) & (ppm): 1.01 (3H, t J=7.4 Hz), Compound (328): Isopropyrideneamino N-(4-meth 1.36 (3H, d, J=7.0 Hz), 1.63-1.74 (2H, m), 2.34 (3H, s), 3.79 ylphenyl)-3-(phenylthio)acrylimidate (1H, m), 6.12(1H, d. J=15.5 Hz), 6.63 (2H, d. J=8.2 Hz), 7.06 (2H, d, J=8.0 Hz), 7.29-7.38 (6H, m). 1724 'H-NMR (CDC1) & (ppm): 2.06 (3H, s), 2.11 (3H, 1713. The stereochemistry of the -CH=CH-bond was s), 2.30 (3H, s), 5.80 (1H, dJ=15.4 Hz), 6.73 (2H, dJ=7.8 Hz), E. 7.03 (2H, d J=8.5 Hz), 7.30-7.52 (6H, m).

US 2011/0319437 A1 Dec. 29, 2011

1792 The stereochemistry of the —CH=CH-bond was 1802 The stereochemistry of the —CH=CH-bond was E. E. Example 336 Example 341 Compound (383): Cyclohexylmethyl 3-(4-methoxy Compound (373): Cyclohexylmethyl 3-(4-fluoroben benzylthio)-N-(4-methylphenyl)-thioacrylimidate Zylthio)-N-(4-methylphenyl)-thioacrylimidate 1803 'H-NMR (CDC1,) & (ppm): 1.00-1.25 (5H, m), 1793 'H-NMR (CDC1) & (ppm): 1.02-1.25 (5H, m), 1.66-1.86 (6H, m), 2.32 (3H, s), 2.97 (2H, d J=6.8 Hz), 3.80 1.66-1.85 (6H, m), 2.33 (3H, s), 2.97 (2H, d J=6.8 Hz), 3.82 (3H, s), 3.81 (2H, s), 6.10 (1H, d J=15.4 Hz), 6.62 (2H, d (2H, s), 6.06 (1H, d J=15.4 Hz), 6.59 (2H, d J=8.1 Hz), 6.95 J=8.3 Hz), 6.81 (2H, d J=8.8 Hz), 7.07 (2H, dJ=8.1 Hz), 7.11 (2H, d J=8.6 Hz), 7.27 (1H, d J=15.7 Hz). (2H, t J=8.7 Hz) 7.06 (2H, d J–7.8 Hz), 7.12-7.16 (2H, m), 1804. The stereochemistry of the —CH=CH-bond was 7.23 (1H, d J=15.4 Hz). E. 1794. The stereochemistry of the -CH=CH-bond was 1805 Compound (385) was synthesized in a similar man E. ner as the Example 176. Example 337 Example 342 Compound (375): Cyclohexylmethyl 3-(4-methyl Compound (385): 1-Phenylethylideneamino N-(4- benzylthio)-N-(4-methylphenyl)-thioacrylimidate methylphenyl)-3-(phenylthio) thioacrylimidate 1806 'H-NMR (CDC1) & (ppm): 2.17 (0.96H, s), 2.31 1795 H-NMR (CDC1) & (ppm): 1.02-1.26 (5H, m), (3H, s), 2.45 (2.04H, s), 5.88 (0.83H, d J=15.4 Hz), 6.59 1.70-1.83 (6H, m), 2.32 (3H, s), 2.33 (3H, s), 2.97 (2H, d (0.17H, d J=15.1 Hz), 6.76 (2H, d J=8.0 Hz), 6.98-7.08 (3H, J=6.8 Hz), 3.81 (2H, s), 6.10 (1H, d J=15.4 Hz), 6.61 (2H, d m), 7.32-7.54 (8H, m), 7.74-7.78 (2H, m). J=8.1 Hz), 707-7.08 (6H, m), 7.27 (1H, d J=15.4 Hz). 1807. The stereochemistry of the -CH=CH-bond was 1796. The stereochemistry of the -CH=CH-bond was E. E. 1808 Compound (386) was synthesized in a similar man ner as the Example 161. Example 338 Example 343 Compound (377): Cyclohexylmethyl 3-(4-chlo Compound (386): 2-Phenylethyl N-(4-methylphe robenzylthio)-N-(4-methylphenyl)-thioacrylimidate nyl)-3-(phenylthio)thioacrylimidate 1809 'H-NMR (CDC1) & (ppm): 2.32 (3H, s), 2.98 (2H, 1797 'H-NMR (CDC1) & (ppm): 1.02-1.25 (5H, m), tJ=7.7 Hz), 3.30 (2H, tJ=7.7 Hz), 6.14 (1H, d, J=15.6 Hz), 1.70-1.85 (6H, m), 2.33 (3H, s), 2.97 (2H, d J=6.6 Hz), 3.81 6.64 (2H, d, J=8.00 Hz), 7.07 (2H, d, J=8.0 Hz), 7.18-7.37 (2H, s), 6.04 (1H, d J=15.4 Hz), 6.58 (2H, d J=8.1 Hz), 7.06 (11H, m). (2H, d J=8.1 Hz), 7.10 (2H, d J=8.3 Hz), 7.14-7.30 (3H, m). 1810. The stereochemistry of the -CH=CH-bond was 1798. The stereochemistry of the -CH=CH-bond was E. E. Example 344 Example 339 Compound (387): Phenyl N-ethoxycarbonyl-3-(phe nylthio)thioacrylimidate Compound (379): Cyclohexylmethyl 3-(2,4-dichlo robenzylthio)-N-(4-methylphenyl)-thioacrylimidate 1811 N-ethoxycarbonyl-3-(phenylthio)acrylamide (1.20 g) was dissolved to acetonitrile (30 ml), then carbon tetrabro mide (2.83 g) and triphenylphosphine (2.23 g) was added 1799 H-NMR (CDC1) & (ppm): 1.01-1.23 (5H, m), thereto and heat refluxing for three hours. The reaction mix 1.70-1.86 (6H, m), 2.32 (3H, s), 2.98 (2H, d J=6.8 Hz), 3.92 ture was concentrated under reduced pressure. The residue (2H, s), 6.03 (1H, d J=15.4 Hz), 6.57 (2H, d J=8.1 Hz), 7.04 was subjected to silica gel column chromatography (hexane: (2H, d J=8.1 Hz), 7.19-7.35 (4H, m). ethyl acetate20:1) to obtain light yellow oil. It was dissolved 1800. The stereochemistry of the -CH=CH-bond was to DMF (10 ml), then sodium salt of thiophenol (0.63 g) was E. added thereto under ice cooling and stirred at room tempera ture for two hours.t-Butyl methyl ether (100 ml) was added to Example 340 the reaction mixture, washed Successively with 1N aqueous Sodium hydroxide solution, water and aqueous saturated Compound (381): Cyclohexylmethyl 3-(2-methyl Sodium chloride solution, dried over anhydrous Sodium Sul benzylthio)-N-(4-methylphenyl)-thioacrylimidate fate, filtered off inorganic salt and concentrated under reduced pressure. The residue was purified by medium pres 1801 H-NMR (CDC1) & (ppm): 1.00-1.26 (5H, m), Sure preparative high performance liquid chromatography to 1.66-1.86 (6H, m), 2.30 (3H, s), 2.31 (3H, s), 2.98 (2H, d obtain phenyl N-ethoxycarbonyl-3-(phenylthio)thio J=6.8 Hz), 3.85 (2H, s), 6.10 (1H, d J=15.7 Hz), 6.63 (2H, d acrylimidate (0.40 g) as light yellow oil. J=8.1 Hz), 7.06(2H, dJ=8.1 Hz)7. 13-7.18 (4H, m), 7.30 (1H, 1812 'H-NMR (CDC1) & (ppm): 1.28 (2.3H, t, J–7.2 Hz), dJ=15.4 Hz). 1.40 (0.70H, t, J=7.1 Hz), 4.15 (1.5H, q, J=7.2 Hz), 4.30

US 2011/0319437 A1 Dec. 29, 2011

Hz), 6.58 (1H, d, J–7.8 Hz), 6.70 (1H, s), 6.99 (1H, d, J=7.8 Example AA3 Hz), 7.15 (1H, t, J=7.8 Hz), 7.26-7.46 (6H, m) Compound AA8-2: 1-cyclopentylethyl 3-(4-fluo Compound AA10-1563: cyclohexylmethyl N-(3- rophenylthio)-N-(phenyl)thioacrylimidate chlorophenyl)-3-(4-fluorophenylthio)thioacrylimi date 2110 2104 -()--in-l--(i ) 2111 Ethynyl trimethylsilane (1.0 mL) was dissolved in dry THF (20 mL), n-butyllithium/hexane solution(1.57 moL/ L:5 mL) was added dropwise thereto at -78°C., and then it 2105 H-NMR (CDC1,) & (ppm): 0.92-1.31 (5H, m), was warmed to 0°C. THF (2 mL) solution of phenyl isothio 1.50-190 (6H, m), 2.96 (2H, d, J=6.8 Hz), 5.77 (1H, d, J=15.5 cyanate (0.88 mL) was added thereto, THF (2 mL) solution of Hz), 6.56 (1H, d, J=8.0 Hz), 6.67 (1H, s), 6.97-7.06 (3H, m), 1-cyclopentylethyl methanesulfonate (1.55 g) was added 7.15 (1H, t, J=8.0 Hz), 7.28-7.40 (3H, m) thereto, and then it was refluxed for 7 hours. Saturated aque Compound AA10-1339: cyclohexylmethyl ous solution of ammonium chloride (10 mL) and water (10 N-(3-fluorophenyl)-3-(phenylthio)thioacrylimidate mL) were added to the reaction solution, then it was extracted with t-butyl methyl ether (20 mL). The organic layer was 2106 washed with Saturated aqueous solution of Sodium chloride (20 mL), dried over anhydrous magnesium sulfate. Inorganic salt was filtered off and the filtrate was concentrated under reduced pressure to obtain brown oil (2.22 g). The residue was Subjected to Florisil column chromatography (hexane/ethyl acetate=20/1) to obtain crude 1-cyclopentylethyl N-(phenyl)- 3-(trimethylsilyl)thiopropynimidate (0.98 g). The obtained S crude 1-cyclopentylethyl N-(phenyl)-3-(trimethylsilyl)thio propynimidate (0.98 g) was dissolved to methanol (20 mL), a E Small amount of potassium carbonate was added thereto, and ()--in-l- then stirred for 1 hour at room temperature. Furthermore, 4-fluorothiophenol (0.22 mL) was added to the mixture and 2107 H-NMR (CDC1) & (ppm): 0.92-1.33 (5H, m), stirred for overnight. The reaction Solution was concentrated 149-192 (6H, m), 2.97 (2H, d, J=6.8 Hz), 5.95 (1H, d, J=15.5 under reduced pressure. The residue was subjected to silica Hz), 6.43 (1H, d. J=10.1 Hz), 6.47 (1H, d, J=8.0 Hz), 6.72 gel column chromatography (hexane/ethyl acetate 30/1) to (1H, td, J=8.0, 1.7 Hz), 7.18 (1H, dd, J=14.7, 8.0 Hz), 7.24 obtain 1-cyclopentylethyl 3-(4-fluorophenylthio)-N-(phe 7.46 (6H, M). nyl)thioacrylimidate (0.43 g). H-NMR (CDC1) & (ppm): 1.26-1.89 (11H, m), 2.00-2.10 (1H, m), 3.81-3.88 (1H, m), Compound AA10-1340: cyclohexylmethyl N-(3- 5.91 (1H, dJ=15.4 Hz), 6.69 (2H, dJ=7.6Hz), 6.97-704 (3H, fluorophenyl)-3-(4-fluorophenylthio)thioacrylimidate m), 7.22-7.35 (5H, m). 2112 Below mentioned compounds were synthesized in a 2108 similar manner as the Example AA3. Compound AA4-2: cyclobutylmethyl N-(4-fluo rophenyl)-3-(4-fluorophenylthio)thioacrylimidate 2113 -()--in-l-S 2109 'H-NMR (CDC1,) & (ppm): 0.94-1.31 (5H, m), 1.50-191 (6H, m), 2.97 (2H, d, J=6.8 Hz), 5.81 (1H, d, J=15.5 Hz), 6.40 (1H, d. J=10.1 Hz), 6.45 (1H, d, J=8.0 Hz), 6.73 (1H, td, J=8.0, 2.1 Hz), 7.01 (2H, t, J=8.5 Hz), 7.17 (1H, dd, J=14.7, 8.0 Hz), 7.29-7.40 (3H, m). US 2011/0319437 A1 Dec. 29, 2011 99

2114 H-NMR (CDC1) & (ppm): 1.70- 1.92 (4H, m), Example AB2 2.04-2.14 (2H, m), 2.57-2.65 (1H, m), 3.15 (2H, d. J–7.5 Hz), Compound AB42-2: 1-ethyl-2-methylpentyl 3-(4- 5.93 (1H, d, J=15.5 Hz), 6.68 (2H, d, J=7.2 Hz), 6.96-7.05 fluorophenylthio)-N-(phenyl)thioacrylimidate (3H, m), 7.22-7.34 (5H, m) 2120 Example AB1 Compound AB35-2: 1-ethyl-2-methylbutyl 3-(4- fluorophenylthio)-N-(phenyl)thioacrylimidate 2115

2121 1-ethyl-2-methylpentyl N-phenylpropynthioimi date (0.44 g) was dissolved to chloroform (8 mL), chloroform S (3 mL) solution of 4-fluorothiophenol (0.16 g) was added to the solution under ice-cooling, and then it was stirred for 18 hours at room temperature. The reaction mixture was concen trated under reduced pressure. The obtained residue was sub jected to medium pressure HPLC (hexane/ethyl acetate=98/ 2) to obtain 1-ethyl-2-methylpentyl 3-(4-fluorophenylthio)- N-(phenyl)thioacrylimidate (0.28 g) as pale yellow oil. 2116 1-ethyl-2-methylbutyl N-phenyl-3-(trimethylsilyl) 2122 "H-NMR (CDC1) & (ppm): 0.88 (3H, t, J–7.0 Hz), thiopropynimidate (0.47 g) was dissolved to methanol (10 0.93-1.04 (6H, m), 1.14-1.89 (7H, m), 3.85-3.98 (1H, m), 5.92 (1H, d, J=15.4 Hz), 6.66 (2H, d, J=7.3 Hz), 6.96-7.03 mL). Small amount of potassium carbonate was added to the (3H, m), 7.21-7.35 (5H, m) solution under ice-cooling and then it was stirred for 30 2123 Below mentioned compounds were synthesized in a minutes. Then methanol (3 mL) of 4-fluorothiophenol (0.105 similar manner as the Example AB2. mL) was added to the solution and the mixture was stirred for Compound AB92-2: 2-indanyl 18 hours at room temperature. The reaction mixture was 3-(4-fluorophenylthio)-N-(phenyl)thioacrylimidate concentrated under reduced pressure. The residue was Sub jected to medium pressure HPLC (hexane/ethyl acetate=98/ 2124 2) to obtain 1-ethyl-2-methylbutyl 3-(4-fluorophenylthio)-N- (phenyl)thioacrylimidate (0.09 g). "H-NMR (CDC1) & (ppm): 0.89-1.04 (9H, m), 1.13-1.34 (1H, m), 1.49-1.78 (4H, m), 3.86-3.91 (0.75H, m), 3.97-4.01 (0.25H, m), 5.92 (0.25H, d, J=15.4 Hz), 5.93 (0.75H, d, J=15.4 Hz), 6.66 (2H, d, J=7.6 Hz), 6.97-7.03 (3H, m), 7.21-7.35 (5H, m) 2117 Below mentioned compounds were synthesized in a i similar manner as the Example AB1. -()--in-l--(E. ) Compound AB36-2: 1-ethyl3-methylbutyl 3-(4-fluo rophenylthio)-N-(phenyl)thioacrylimidate 2125 H-NMR (CDC1) & (ppm): 3.01 (1H, d, J=5.9 Hz), 3.05 (1H, d, J=5.9 Hz), 3.48 (1H, d, J=7.8 Hz), 3.52 (1H, d, 2118 J=7.8 Hz), 4.45-4.51 (1H, m), 5.95 (1H, d, J=15.6 Hz), 6.73 (2H, d, J=7.6 Hz), 6.96 (2H, t, J=8.5 Hz), 7.04 (1H, t, J=7.3 Hz), 7.14-7.27 (9H, m) Example 3 Compound AB8-2:4-methylcyclohexyl 3-(4-fluo rophenylthio)-N-(phenyl)thioacrylimidate

S 2126

-()--in-l=s-(E. )

2119 H-NMR (CDC1) & (ppm): 0.92 (6H, d. J=6.6 Hz), 1.00 (3H, t, J=7.3 Hz), 1.40-1.86 (5H, m), 3.89-3.95 (1H, m), 5.92 (1H, d, J=15.6 Hz), 6.67 (2H, d, J=7.6 Hz), 6.96-7.04 (3H, m), 7.21-7.35 (5H, m)