(12) STANDARD PATENT (11) Application No. AU 2016337993 B2 (19) AUSTRALIAN PATENT OFFICE
(54) Title Pyrazine compound and arthropod pest control agent containing same
(51) International Patent Classification(s) C07D 241/18 (2006.01) A61K 31/513 (2006.01) A01N 43/60 (2006.01) A61P 33/00 (2006.01) A01P 7/04 (2006.01) C07D 401/04 (2006.01)
(21) Application No: 2016337993 (22) Date of Filing: 2016.10.13
(87) WIPO No: W017/065228
(30) Priority Data
(31) Number (32) Date (33) Country 2016-149448 2016.07.29 JP 2015-208639 2015.10.23 JP 2015-204376 2015.10.16 JP
(43) Publication Date: 2017.04.20 (44) Accepted Journal Date: 2020.10.08
(71) Applicant(s) Sumitomo Chemical Company, Limited
(72) Inventor(s) Orimoto, Kohei;Nokura, Yoshihiko;Nakajima, Yuji;Tanabe, Takamasa;Kimura, Takahiro
(74) Agent / Attorney Spruson & Ferguson, GPO BOX 3898, Sydney, NSW, 2001, AU (19)~~~10a 0 ,Pi-h . (43) MH %W0 2017 * J 20 (20.04.2017) WO 2017/065228 Al 4 WIPOIPCT
(51) MRMHVF3n0: A M $1W±ii 7] RT H2 1 )Kb C07D 241/18 (2006.01) A61K31/513 (2006.01) 2 ±i$1 Hyogo (JP). 1 t4 I (KIMURA, AG1N 43/60 (2006.01) A61P 33/00 (2006.01) Takahiro); T 6658555 iro );6 78 R T H 2 A01P 7/04 (2006.01) C07D 401/04 (2006.01) 1F it ib7?* nRi h Hyogo(JP). (21) [ R9 : PCT/JP2016/080410 (74) ItT¶A:! ' rat (SAMEJIMA,Mutsumietal.); Ts530007t t ilL- T81 (22) [P, R 6t : 2016 P 10 h 13 E (13.10.2016) R E fE 4i (25) [P, A® iB: 841 Osaka(JP).
(26) [P, :=3ME 8)t-- (81) tt( ®~iR.±®Ift{ _. f ' ): AE, AG, AL, AM, AO, AT, AU, AZ, BA, (30) 4ittr-9: BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, 4 1 2015-204376 2015 P 10 h 16 (16.10.2015) JP CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, 4Ji 2015-208639 2015 P 10 h 23 (23.10.2015) JP ES, Fl, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, 4Ji 2016-149448 2016 P 7 h 29 (29.07.2016) JP IN, IR, IS, JP, KE, KG, KN, KP, KR, KW, KZ, LA, LC, (71) , it : K i4L$t $ $TA (SUMITOMO CHEMIC- LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, AL COMPANY, LIMITED) [JP/JP]; T 1048260 JS MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, 0 ffrVIlfE* T I 2 7 # 1 F Tokyo (JP). PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, (72) 59BEA4: tFT* FI -!(ORIMOTO,Kohei);T6658555 UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. = *MT1 ±$=3]P RT H2 #1 _~ K (84) 0) ®tdZ L , ±r®®6D 6D K ~ihrHyogo (JP).~t Ac-i (NOKURA, Yoshi- i~f= : ARIPO (BW, GH, GM, KE, LR, LS, MW, - hiko ),6555 6658555lid!6 ] T02 1 S4T 66 8i5] Hyogo (JP).tHIT i ~ 'i,NA, RW, SD, SL, ST, SZ, TZ, UG, ZM,ZW), .-L (NAKAIYuiMA66u55;6687 '/ 7 (AM, AZ, BY, KG, KZ, RU, TJ, TM), E - 2ft(I4L, Yujii; Hyogo 66585 / (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, PR TE2#1 i t ) ilL(TNABE TA R 68 ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, - (P). mft AS '1(TANABE,Takamasa); T6658555
(54) Title: PYRAZINE COMPOUND AND ARTHROPOD PEST CONTROL AGENT CONTAINING SAME
R
(57) Abstract: The present invention provides: a compound represented by formula (I) [wherein A' represents a nitrogen atom or 4 4 1 CR ; R represents a hydrogen atom or the like; R represents a C2-C10 linear hydrocarbon group having at least one halogen atom, or the like; R2 represents a Cl-C6 alkyl group which may have at least one halogen atom, or the like; q represents 0, 1, 2 or 3; R3 represents a C1-C6 linear hydrocarbon group which may have at least one halogen atom, or the like; p represents 0, 1, or 2; R rep resents a C1-C6 alkyl group which may have at least one halogen atom, or the like; and n represents 0, 1, or 2] or an N-oxide com Opound thereof; and an arthropod pest control agent which comprises a compound represented by formula (I) and the like and an inert carrier and exhibits an excellent controlling effect against arthropod pests. (57) f [$YT$$] W O 2017/065228 A 1l I |I|I|VII lllI l|||||||||||||I||I|I|I||I|I||||||D||||I||||||||I|
MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, hIj-/'1l"t4: TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW' ((J 21 (3)) KM, ML, MR, NE, SN, TD, TG).
*59B~qit, TA ( I) [TA*, A'lIt, m"!!!!%TTR It C R 4 - L , R 4 It, 7X*T,9T* - L, R 1 It, 1 10/\mY.M&f C 2 -C 1 OMTMM*7X* -A L, R 2 It, 1 gi4-L0)/ my,>Tq T L-CLT\ tJzl\C1 -C67) 4)X L, qit, 0, 1, 2, R3 AL, R 'It, 1ELL0/\1 L'./NT LT \TiLN\C 1 -C6%2T b7X*E AL , pit, 0, 1, Rit2AL, R 6 it, 1 L®/\DY'./L L CtC1 -C167)-6) JUL, TLT, nit, 0, 1 It22t.o ]T-rLFo71 R It)Nl-/FiL , La t ( I) bi L 1
DESCRIPTION
PYRAZINE COMPOUND AND ARTHROPOD PEST CONTROL AGENT
CONTAINING SAME
5
TECHNICAL FIELD
[0001)
This application claims priority to and the benefit of
Japanese Patent Application Nos. 2015-204376 filed October
10 16, 2015, 2015-208639 filed October 23, 2015, and 2016
149448 filed July 29, 2016, the entire contents of which
are incorporated herein by reference.
[0002]
The present invention is related to a certain class of
15 pyrazine compound and its use for controlling harmful
BACKGROUND ART
[0003]
20 To date, some compounds for controlling harmful
arthropods have been developed and come into practical use.
Also, a certain class of compounds has been known to be
effective for controlling harmful organisms (see Patent
Document 1).
25 2
CITATION LIST
PATENT DOCUMENT
£00041
Patent Document 1: JP 2000-26421 A
5
SUMMARY OF THE INVENTION
(PROBLEMS TO BE SOLVED BY INVENTION)
[0005)
An object of the present invention is to provide a
10 compound having an excellent efficacy for controlling
harmful arthropods.
(MEANS TO SOLVE PROBLEMS)
[0006]
15 The present invention provides, for example, the
following embodiments.
[1] A compound represented by formula (I) or its N oxide
compound:
R2 (O)oS
3 R 1-O N x(R )g (RRG
20 [wherein
A represents a nitrogen atom or a CR4 ;
2 R 4 represents a hydrogen atom, a OP2, a NR R, a 3
cyano group, a nitro group, or a halogen atom;
R1 represents a C2-C10 chain hydrocarbon group having
one or more halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group
having one or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2
5 C5 alkyl group having one or more halogen atoms, a (Cl-C5
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl group having one or
more halogen atoms, a (C3-C7 cycloalkyl)Cl-C3 alkyl group
having one or more substituents selected from Group G, or a
10 C3-C7 cycloalkyl group having one or more substituents
selected from Group G;
R 2 represents a C1-C6 alkyl group optionally having one
or more halogen atoms, a cyclopropylmethyl group, or a
cyclopropyl group;
15 q represents 0, 1, 2, or 3;
R3 represents independently of each other, a C1-C6 chain
hydrocarbon group optionally having one or more substituents
selected from Group B, a phenyl group optionally having one
or more substituents selected from Group D, a 5 or 6 membered
20 aromatic heterocyclic group optionally having one or more
substituents selected from Group D, a OR 2 , a NR"R'2, a
NRiiaRi 2 a, a NR 2 9NRlRi 2 , a NR 29OR", a NR"C(O)R 3 , a NR29NR"C(O)R 3 ,
a NR"lC (0) OR14 , a NR2 9NR"C (0) OR1 4, a NR"lC (0) NR1 5Ris, a
NR 24NR"C(0)NR1 5R'6 , a N=CHNR1 5R' 6 , a N=S(0)xR 5R 6, a S(0)yR'5, a
25 C(O)OR1 7, a C(O)NRlRi 2 , a cyano group, a nitro group, or a
/ n n 1 /I 1 1 \ .nI I 4
halogen atom, and when q is 2 or 3, a plurality of R3 may be
identical or different;
p represents 0, 1, or 2,
R6 represents independently of each other, a C1-C6 alkyl
5 group optionally having one or more halogen atoms, a OR 8 , a
NR18R19, a cyano group, a nitro group, or a halogen atom, and
when p is 2, a plurality of R6 may be identical or different;
8 R'', R17, R' , R1 9 , R 24 and R2 9 represent independently of
each other a hydrogen atom, or a C1-C6 chain hydrocarbon
10 group optionally having one or more halogen atoms;
Ri 2 represents a hydrogen atom, a C1-C6 chain hydrocarbon
group optionally having one or more halogen atoms, a C1-C6
alkyl group having one substituent selected from Group F, or
23 a S (0) 2 R ;
15 R 2 3 represents a C1-C6 chain hydrocarbon group optionally
having one or more halogen atoms, or a phenyl group
optionally having one or more substituents selected from
Group D;
Ria and R2a combine together with a nitrogen atom to
20 which they are attached to form a 3 to 7 membered nonaromatic
heterocyclic group optionally having one or more substituents
selected from Group E {the 3 to 7membered nonaromatic
heterocyclic group represents aziridine, azetidine,
pyrrolidine, imidazoline,
/ n n 1 /I 1 1 \ .nI I 5
imidazolidine, piperidine, tetrahydropyrimidine,
hexahydropyrimidine, piperazine, azepane, oxazolidine,
isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane,
thiazolidine, isothiazolidine, 1,3-thiazinane,
5 thiomorpholine, or 1,4-thiazepane};
R3 represents a hydrogen atom, a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a C3-C7 cycloalkyl group optionally having one or
more halogen atoms, a (C3-C6 cycloalkyl)Cl-C3 alkyl group
10 optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
Group D, or a 5 or 6 membered aromatic heterocyclic group
optionally having one or more substituents selected from
Group D;
15 R" represents a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a C3-C7
cycloalkyl group optionally having one or more halogen
atoms, a (C3-C6 cycloalkyl)Cl-C3 alkyl group optionally
having one or more halogen atoms, or a phenylCl-C3 alkyl
20 group {the phenyl moiety in the phenylCl-C3 alkyl group may
optionally have one or more substituents selected from
Group D};
5 R' and R represent independently of each other, a
Cl-C6 alkyl group optionally having one or more halogen
25 atoms; 6
R2 7 and R2 8 represent independently of each other, a
hydrogen atom, or a Cl-C6 alkyl group optionally having one
or more halogen atoms;
n and y represent independently of each other, 0, 1,
5 or 2;
x represents 0 or 1;
Group B: a group consisting of a Cl-C6 alkoxy group
optionally having one or more halogen atoms, a C3-C6
alkenyloxy group optionally having one or more halogen
10 atoms, a C3-C6 alkynyloxy group optionally having one or
more halogen atoms, a Cl-C6 alkylsulfanyl group optionally
having one or more halogen atoms, a Cl-C6 alkylsulfinyl
group optionally having one or more halogen atoms, a Cl-C6
alkylsulfonyl group optionally having one or more halogen
15 atoms, a C3-C6 cycloalkyl group optionally having one or
more halogen atoms, a cyano group, a hydroxy group, and a
halogen atom;
Group C: a group consisting of a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
20 atoms, a Cl-C6 alkoxy group optionally having one or more
halogen atoms, a C3-C6 alkenyloxy group optionally having
one or more halogen atoms, a C3-C6 alkynyloxy group
optionally having one or more halogen atoms, and a halogen
atom;
25 Group D: a group consisting of a Cl-C6 chain 7
hydrocarbon group optionally having one or more halogen
atoms, a hydroxy group, a C-C6 alkoxy group optionally
having one or more halogen atoms, a C3-C6 alkenyloxy group
optionally having one or more halogen atoms, a C3-C6
5 alkynyloxy group optionally having one or more halogen
atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group
optionally having one or more halogen atoms, a Cl-C6
alkylsulfinyl group optionally having one or more halogen
atoms, a Cl-C6 alkylsulfonyl group optionally having one or
10 more halogen atoms, an amino group, a NHR, a NR2 R21, a
C (O)R, a OC(O)R2, a C (0) OR, a cyano group, a nitro group,
and a halogen atom {R2 1 and R22 represent independently of
each other a Cl-C6 alkyl group optionally having one or
more halogen atoms};
15 Group E: a group consisting of a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a Cl-C6 alkoxy group optionally having one or more
halogen atoms, a C3-C6 alkenyloxy group optionally having
one or more halogen atoms, a C3-C6 alkynyloxy group
20 optionally having one or more halogen atoms, a halogen atom,
an oxo group, a hydroxy group, a cyano group, and a nitro
group;
Group F: a group consisting of a Cl-C6 alkoxy group
optionally having one or more halogen atoms, an amino group,
25 a NHR21 , a NR2 1R22, a cyano group, a phenyl group optionally 8
having one or more substituents selected from Group D, a 5
or 6 membered aromatic heterocyclic group optionally having
one or more substituents selected from Group D, a C3-C7
cycloalkyl group optionally having one or more halogen
5 atoms, and a 3 to 7 membered nonaromatic heterocyclic group
optionally having one or more substituents selected from
Group C;
Group G: a group consisting of a halogen atom, and a
C1-C6 haloalkyl group].
10 [2] The compound described in [1] wherein R4 represents a
hydrogen atom or a halogen atom, and R3 represents a C1-C6
chain hydrocarbon group optionally having one or more
halogen atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
15 heterocyclic group containing one to two nitrogen atoms
{the 6 membered aromatic heterocyclic group optionally has
one or more substituents selected from Group D}, a 5
membered aromatic heterocyclic group containing one to four
nitrogen atoms {the 5 membered aromatic heterocyclic group
20 optionally has one or more substituents selected from Group
D}, a OR1 2 , a NR11R1 2 , or a halogen atom.
[3] The compound described in [1] wherein R3 represents a
C1-C6 alkyl group having one or more halogen atoms, a OR1 2 ,
a NR11R1 2 , or a halogen atom, and R" and R1 2 represent
25 independently of each other a hydrogen atom or a C1-C3
/ n n 1 /I 1 1 \ .nI I 9
alkyl group optionally having one or more halogen atoms.
[4] The compound described in [1] wherein q is 0.
[5] The compound described in any one of [1] to [4]
wherein p is 0 or 1, and R 6 represents a C1-C6 alkyl group
5 optionally having one or more halogen atoms, or a halogen
atom.
[6] The compound described in any one of [1] to [4]
wherein p is 0.
[7] The compound described in any one of [1] to [5]
10 wherein R' represents a C2-C10 haloalkyl group.
[8] The compound described in any one of [1] to [6]
wherein R' represents a C2-C10 fluoroalkyl group.
[9] The compound described in any one of [1] to [6]
wherein R' represents a C2-C10 alkyl group having two or
15 more fluorine atoms.
[10] The compound described in any one of [1] to [6]
wherein R' represents a C3-C5 alkyl group having four or
more fluorine atoms.
[11] The compound described in any one of [1] to [10]
20 wherein R2 represents a C1-C6 alkyl group optionally having
one or more halogen atoms.
[12] The compound described in any one of [1] to [10]
wherein R 2 represents an ethyl group.
[13] The compound described in [1] wherein
25 R' represents a C2-C10 haloalkyl group;
/ n 1 /I 1 1 \ .nI I 10
R 2 represents an ethyl group;
q is 0 or 1, and R3 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom; and
5 p is 0 or 1, and R6 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom.
[14] The compound described in [1] wherein
R 1 represents a C3-C5 alkyl group having four or more
10 fluorine atoms;
R2 represents an ethyl group;
q is 0; and
p is 0.
[151 A composition comprising the compound described in any
15 one of [11 to [14], and one or more ingredients selected
from the group consisting of Groups (a), (b), (c), and (d):
Group (a): a group consisting of insecticidal ingredients,
miticidal ingredients, and nematicidal ingredients;
Group (b): fungicidal ingredients;
20 Group (c): plant growth modulating ingredients; and
Group (d): phytotoxicity-reducing ingredients.
[16] A method for controlling a harmful arthropod which
comprises applying an effective amount of the compound
described in any one of [1] to [14] or the composition
25 described in [15] to a harmful arthropod or a habitat where 11
a harmful arthropod lives.
[17] A method for controlling a harmful arthropod which
comprises applying an effective amount of the compound
described in any one of [1] to [14] or the composition
5 described in [15] to a plant or soil for growing a plant.
[18] A method for controlling a harmful arthropod which
comprises applying an effective amount of the compound
described in £1] to [14] or the composition described in
[15] to a seed or bulb.
10 [19] A seed or bulb carrying an effective amount of the
compound described in any one of [1] to [14] or the
composition described in [15).
[20] An agent for controlling a harmful arthropod
comprising the compound described in any one of [1] to [14]
15 or the composition described in [15], and an inert carrier.
[21] A compound represented by formula (M-3):
R2 (O)nS (R 3)q HN N A'
(R6)p (M-3)
[wherein
A represents a nitrogen atom or a CR 4 ;
20 R' represents a hydrogen atom, a OR2 7 , a NR 7 R, a 12
cyano group, a nitro group, or a halogen atom;
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms, a cyclopropylmethyl group, or a
cyclopropyl group;
5 q represents 0, 1, 2, or 3;
R3 represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
substituents selected from Group B, a phenyl group
optionally having one or more substituents selected from
10 Group D, a 5 or 6 membered aromatic heterocyclic group
optionally having one or more substituents selected from
Group D, a OR', a NRi'Ri, a NRuaRia, a NR2SNR±R 1 , a NR2ORiL,
a NR"C (O) R', a NR'NRC (O) Rl, a NRC (O) OR, a
NR29NRC (O) OR", a NR"C (O)NRR, a NR4INRiC (Q) NRR1, a
i5 161i 15 N=CHNR R, a N=S (O),RR, a S (0) yR, a C (O) OR", a
C(O)NR"R", a cyano group, a nitro group, or a halogen atom,
and when q is 2 or 3, a plurality of R3 may be identical or
different;
p represents 0, 1, or 2; and
20 R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, a
OR , a NR R , a cyano group, a nitro group, or a halogen
atom, and when p is 2, a plurality of R6 may be identical
or different}.
25 [223 A compound represented by formula (M-4): 13
R 2 (O)nS (R 3)q V N N A1
(Ra (M-4)
[wherein
V represents a halogen atom;
A represents a nitrogen atom or a CR4;
5 R 4 represents a hydrogen atom, a OR27 , a NR2'R", a
cyano group, a nitro group, or a halogen atom;
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms, a cyclopropylmethyl group, or a
cyclopropyl group;
10 q represents 0, 1, 2, or 3;
R2 represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
substituents selected from Group B, a phenyl group
optionally having one or more substituents selected from
15 Group D, a 5 or 6 membered aromatic heterocyclic group
optionally having one or more substituents selected from
Group D, a OR', a NRR2, a N29Pu, a N2RRR, a NR'OR"
a NR"C()R, a NR 2 NRC (0)PR, a NR"C (0) OR', a
NRNRC (O) OR", a NR"C (O) NR5 R, a NR2 NR"C (O) NRDR, a
20 N=CHNR 1 R', a N=S (O) xR 1 R, a S (O) R', a C(O)OR 7 , a 14
C(O)NR"R12 , a cyano group, a nitro group, or a halogen
atom, and when q is 2 or 3, a plurality of R3 may be
identical or different;
p represents 0, 1, or 2; and
5 R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, a
OR, a NR'8 R, a cyano group, a nitro group, or a halogen
atom, and when p is 2, a plurality of R6 may be identical
or different].
10 [23] A compound represented by formula (M-30):
R2
R 40 N
(Rk (M-30)
[wherein
R40 represents a halogen atom, a Cl-C4 alkoxy group,
or a OR';
15 RI represents a C2-C1O chain hydrocarbon group having
one or more halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl
group having one or more halogen atoms, a (Cl-C5
alkylsulfanyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfinyl)C2-C5 alkyl group having one
20 or more halogen atoms, a (Cl-C5 alkylsulfonyl)C2-CS alkyl 15
group having one or more halogen atoms, a (C3-C7
cycloalkyl)C1-C3 alkyl group having one or more
substituents selected from Group G, or a C3-C7 cycloalkyl
group having one or more substituents selected from Group
S G;
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms, a cyclopropylmethyl group, or a
cyclopropyl group;
p represents 0, 1, or 2; and
10 R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, a
OR, a NR18R'9 , a cyano group, a nitro group, or a halogen
atom, and when p is 2, a plurality of R6 may be identical
or different].
15 [24] A compound represented by formula (M-31):
R2 (o)ns
R40
N 7 NH 2 (R6)p (M-31)
[wherein
R 40 represents a halogen atom, a Cl-C4 alkoxy group,
or a OR';
20 RI represents a C2-C10 chain hydrocarbon group having 16
one or more halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl
group having one or more halogen atoms, a (Cl-C5
alkylsulfanyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfinyl)C2-C5 alkyl group having one
5 or more halogen atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl
group having one or more halogen atoms, a (C3-C7
cycloalkyl)Cl-C3 alkyl group having one or more
substituents selected from Group G, or a C3-C7 cycloalkyl
group having one or more substituents selected from Group
10 G;
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms, a cyclopropylmethyl group, or a
cyclopropyl group;
p represents 0, 1, or 2; and
15 R6 represents independently of each other a C1-C6
alkyl group optionally having one or more halogen atoms, a
OR, a NR'8R'9 , a cyano group, a nitro group, or a halogen
atom, and when p is 2, a plurality of R6 may be identical
or different].
20
[EFFECT OF INVENTION]
[0007]
The Present compound has an excellent control efficacy
against harmful arthropods, and is thus useful as an active
25 ingredient of an agent for controlling harmful arthropods. 17
Also, a composition comprising the Present compound and one
or more ingredients selected from the group consisting of
Groups (a), (b), (c) and (d) (hereinafter, referred to as
"Present composition") shows an excellent control effect
5 against harmful arthropods.
MODE FOR CARRYING OUT THE INVENTION
[0008)
The substituent(s) as described herein is/are
10 explained.
The term of "optionally having one or more halogen
atoms" represents that when two or more halogen atoms are
present, these halogen atoms may be identical to or
different from each other.
15 The expression of "CX-CY" as used herein represents
that the number of carbon atom is from X to Y. For example,
the expression of "Cl-C6" represents that the number of
carbon atom is from 1 to 6.
[0009]
20 The term of "halogen atom" represents fluorine atom,
chlorine atom, bromine atom, or iodine atom.
[0010]
The term of "chain hydrocarbon group" represents an
alkyl group, an alkenyl group, or an alkynyl group.
25 Examples of the term of "alkyl group" include methyl 18
group, ethyl group, propyl group, isopropyl group, 1,1
dimethylpropyl group, 1,2-dimethylpropyl group, 1
ethylpropyl group, butyl group, tert-butyl group, pentyl
group, hexyl group, heptyl group, octyl group, nonyl group,
5 and decyl group.
Examples of the term of "alkenyl group" include vinyl
group, 1-propenyl group, 2-propenyl group, 1-methyl-1
propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-l
propenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-1
10 propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group,
4-pentenyl group, 5-hexenyl group, heptenyl group, octenyl
group, nonenyl group, and decenyl group.
Examples of the term of "alkynyl group" includes
ethynyl group, 1-propynyl group, 2-propynyl group, 1
15 methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1
ethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group,
5-hexynyl group, heptynyl group, octinyl group, nonynyl
group, and decynyl group.
[0011]
20 The term of "C2-C10 chain hydrocarbon group having one
or more halogens" represents a C2-C1O alkyl group, a C2-C10
alkenyl group, a C2-C10 alkynyl group, each having one or
more halogens.
The term of "C2-C10 haloalkyl group" represents a
25 group wherein one or more hydrogen atoms in the C2-C10 19
alkyl group is/are substituted by halogen atoms, and
includes, for example, a C2-C10 fluoroalkyl group.
Examples of the term of "C2-C10 haloalkyl group" include
chloroethyl group, 2,2,2-trifluoroethyl group, 2-bromo
5 1,1,2,2-tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl
group, 1-methyl-2,2,3,3-tetrafluoropropyl group,
perfluorohexyl group, and perfluorodecyl group.
Examples of the term of "C2-C10 fluoroalkyl group"
include 2,2,2-trifluoroethyl group, 2,2,3,3
10 tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl
group, perfluorohexyl group, and perfluorodecyl group.
Examples of the term of "C2-C10 alkyl group having two
or more fluoro atoms" include 2,2,2-trifluoroethyl group,
2,2,3,3-tetrafluoropropyl group, -methyl-2,2,3,3
15 tetrafluoropropyl group, perfluorohexyl group, and
perfluorodecyl group.
Examples of the term of "C2-C10 alkyl group having
four or more fluoro atoms" include 2,2,3,3
tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl
20 group, perfluorohexyl group, and perfluorodecyl group.
The term of "C2-C10 haloalkenyl group" represents a
group wherein one or more hydrogen atoms in the C2-C10
alkenyl group is/are substituted by halogen atoms, and
includes, for example, a C2-C10 fluoroalkenyl group.
25 Examples of the "C2-C10 fluoroalkenyl group" includes, for 20
example, 4,4,4-trifluoro-2-butenyl group, and 2,4,4,4
tetrafluoro-2-butenyl group.
The term of "C2-C10 haloalkynyl group" represents a
group wherein one or more hydrogen atoms in the C2-C10
5 alkynyl group is/are substituted by halogen atoms, and
includes, for example, a C2-C10 fluoroalkynyl group.
Examples of the "C2-C10 fluoroalkynyl group" includes, for
example, 4,4,4-trifluoro-2-butynyl group.
Examples of the term of "C1-C6 alkyl group optionally
10 having one or more halogen atoms" include 2,2,2
trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group, and
2,2,3,4,4,4-hexafluoropropyl group.
The term of "C1-C6 chain hydrocarbon group having one
or more halogen atoms" represents a C1-C6 alkyl group, a
15 C1-C6 alkenyl group, or a C1-C6 alkynyl group, each having
one or more halogen atoms. The term of "C1-C6 alkyl group
having one or more halogen atoms" is encompassed into the
above-mentioned terms of "C1-C6 alkyl group optionally
having one or more halogen atoms" and the above-mentioned
20 term of "C2-C10 chain hydrocarbon group having one or more
halogen atoms". The term of "C1-C6 alkenyl group having
one or more halogen atoms" and the term of "C1-C6 alkynyl
group having one or more halogen atoms" are encompassed
into the above-mentioned term of "C2-C10 chain hydrocarbon
25 group having one or more halogen atoms".
/ n n 1 /I 1 1 \ .nI I 21
[0012)
Examples of the term of "cycloalkyl group" include
cyclopropyl group, cyclobutyl group, cyclopentyl group,
cyclohexyl group, and cycloheptyl group.
5 [0013]
The term of "alkoxy group" represents a monovalent
group wherein the above-mentioned alkyll group" binds to an
oxygen atom, and examples of a Cl-C6 alkoxy group include
methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, t-butoxy,
10 s-butoxy, and 3-methylbutoxy.
[0014]
Examples of the term of "3 to 7 membered nonaromatic
heterocyclic group" include aziridine, azetidine,
pyrrolidine, imidazoline, imidazolidine, piperidine,
15 tetrahydropyrimidine, hexahydropyrimidine, piperazine,
azepane, oxazolidine, isooxazolidine, 1,3-oxazinane,
morpholine, 1,4-oxazepane, thiazolidine, isothiazolidine,
1,3-thiazinane, thiomorpholine, and 1,4-thiazepane.
Examples of the 3 to 7 membered nonaromatic heterocyclic
20 group optionally having one or more substituents selected
from Group E include the followings: 22
\ \ \ \ \ 0O NO'CH 3\ N 0
F O N NC F F N N 0a N N 'CH3 N N 4\NN, N0 N NCH3 0 0 [0015]
Examples of the term of "phenylCl-C3 alkyl group {the
phenyl moiety in the phenylCl-C3 alkyl group may optionally
5 have one or more substituents selected from Group D}]
include benzyl group, 2-fluorobenzyl group, 4-chlorobenzyl
group, 4-(trifluoromethyl)benzyl group, and 2-[4
(trifluoromethyl)phenyllethyl group.
[0016]
10 The term of "(Cl-CS alkoxy)C2-C5 alkyl group having
one or more halogen atoms" represents a group wherein the
(Cl-CS alkoxy) and/or the (C2-C5 alkyl) have/has one or
more halogen atoms, and includes, for example, 2
(trifluoromethoxy)ethyl group, 2,2-difluoro-3-methoxypropyl
15 group, 2,2-difluoro-3-(2,2,2-trifluoroethoxy)propyl group,
and 3-(2-chloroethoxy)propyl group.
The term of "(Cl-C5 alkylsulfanyi)C2-C5 alkyl group
having one or more halogen atoms" represents a group
wherein the (Cl-CS alkylsulfanyl) and/or the (C2-C5 alkyl)
20 have/has one or more halogen atoms, and includes, for
example, 2,2-difluoro-2-(trifluoromethylthio))ethyl group. 23
The term of "(Cl-CS alkylsulfinyl)C2-C5 alkyl group
having one or more halogen atoms" represents a group
wherein the (Cl-C5 alkylsulfinyl) and/or the (C2-C5 alkyl)
have/has one or more halogen atoms, and includes, for
5 example, 2,2-difluoro-2-(trifluoromethansulfinyl)ethyl
group.
The term of "(Cl-CS alkylsulfonyl) C2-CS alkyl group
having one or more halogen atoms" represents a group
wherein the (Cl-CS alkylsulfonyl) and/or the (C2-CS alkyl)
10 group have/has one or more halogen atoms, and includes, for
example, 2,2-difluoro-2-(trifluoromethansulfonyl)ethyl
group.
The term of "(C3-C6 cycloalkyl)Cl-C3 alkyl group
having one or more halogen atoms" represents a group
15 wherein the (C3-C6 cycloalkyl) and/or the (Cl-C3 alkyl)
has/have one or more halogen atoms, and includes, for
example, (2,2-difluorocyclopropyl)methyl group, 2
cyclopropyl-1,1,2,2-tetrafluoroethyl group, and 2-(2,2
difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group.
20 [0017]
The term of "(C3-C7 cycloalkyl)Cl-C3 alkyl group
having one or more substituents selected from Group G"
represents a group wherein the (C3-C7 cycloalkyl) and/or
the (Cl-C3 alkyl) has/have one or more substituents
25 selected from Group G, and includes, for example, (2,2- 24
difluorocyclopropyl)methyl group, [1
(trifluoromethyl)cyclopropyl]methyl group, [2
(trifluoromethyl)cyclopropyllmethyl group, 2-cyclopropyl
1,1,2,2-tetrafluoroethyl group, 2-cyclopropyl-3, 3, 3
5 trifluoropropyl group, and 1,1,2,2-tetrafluoro-2-[2
(trifluoromethyl)cyclopropyl]ethyl group..
The term of "C3-C7 cycloalkyl group having one or more
substituents selected from Group G" includes, for example,
2,2-difluorocyclopropyl group, 1-(2,2,2
10 trifluoroethyl)cyclopropyl group, and 4
trifluoromethyl)cyclohexyl group,
[0018]
The term of "5 or 6 membered aromatic heterocyclic
group" represents a 5 membered aromatic heterocyclic group
15 or a 6 membered aromatic heterocyclic group. Examples of
the 5 membered aromatic heterocyclic group include pyrrolyl
group, furyl group, thienyl group, pyrazolyl group,
imidazolyl group, triazolyl group, tetrazolyl group,
oxazolyl group, isoxazolyl group, thiazolyl group,
20 oxadiazolyl group, and thiadiazolyl group. Examples of the
6 membered aromatic heterocyclic group include pyridyl
group, pyridazinyl group, pyrimidinyl group and pyrazinyl
group.
The term of "6 membered aromatic heterocyclic group
25 containing one to two nitrogen atoms" represents pyridyl 25
group, pyridazinyl group, pyrimidinyl group and pyrazinyl
group.
The term of "5 membered aromatic heterocyclic group
containing one to four nitrogen atoms" represents pyrrolyl
5 group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl
group, 1,2,3-triazolyl group, and tetrazolyl group.
[0019]
The terms of "alkylsulfanyl", "alkylsulfinyl", and
"alkylsulfonyl" represent an alkyl group containing a S(O)z
10 moiety, respectively.
For example, example of the "alkylsulfanyl" when z is
0 includes methylsulfanyl group, ethylsulfanyl group,
propylsulfanyl group, and isopropylsulfanyl group.
For example, example of the "alkylsulfinyl" when z is
15 1 includes methylsulfinyl group, ethylsulfinyl group,
propyisulfinyl group, and isopropylsulfinyl group.
For example, example of the "alkylsulfonyl" when z is
2 includes methylsulfonyl group, ethylsulfonyl group,
propylsulfonyl group, and isopropylsulfonyl group.
20 [0020]
Example of "N oxide compound" includes a compound
represented by formula (I-Nl), a compound represented by
formula (I-N2), a compound represented by formula (I-N3),
and a compound represented by formula (I-N4). 26
0, /R2 0- I O'S
R-O N (I-N1) N A' (R),
[wherein the symbols are the same as defined above.]
O, S R2 0 R'-O / (R3)q (I-N2)
(Rra),
[wherein the symbols are the same as defined above.]
o.-. /R /0- O`
R 1-O / (R)g (I-N3) N-6 N O 5 (R% [wherein the symbols are the same as defined above.]
\N(R3 (-N4) N N4 ( Ro
[wherein the symbols are the same as defined above.]
[0021]
10 Examples of the Present compound include the following
compounds.
[0022]
A compound of the present invention wherein A' 27
represents a nitrogen atom or a CR4, and R4 represents a
hydrogen atom or a halogen atom;
A compound of the present invention wherein A
represents a nitrogen atom or a CH;
5 [0023]
A compound of the present invention wherein R'
represents a C2-C1O haloalkyl group or a (C3-C7
cycloalkyl)Cl-C3 alkyl group having one or more
substituents selected from Group G;
10 A compound of the present invention wherein R1
represents a C2-C10 haloalkyl group;
A compound of the present invention wherein R'
represents a C2-C10 alkyl group having two or more fluoro
atoms;
15 A compound of the present invention wherein R1
represents a C2-C6 alkyl group having four or more fluoro
atoms;
[0024]
A compound of the present invention wherein R2
20 represents a Cl-C6 alkyl group optionally having one or
more halogen atoms;
A compound of the present invention wherein R2
represents a Cl-C6 alkyl group;
A compound of the present invention wherein R 2
25 represents a methyl group or an ethyl group; 28
A compound of the present invention wherein R2
represents an ethyl group;
[0025]
A compound of the present invention wherein R3
5 represents independently of each other a Cl-C6 chain
hydrocarbon group optionally having one or more
substituents selected from Group B, a phenyl group
optionally having one or more substituents selected from
Group D, a 5 or 6 membered aromatic heterocyclic group
10 optionally having one or more substituents selected from
Group D, a OR, a NR"R', a NRuaR'a, a S (O) yR', or a
halogen atom;
A compound of the present invention wherein q
represents 0, 1 or 2, and R3 represents independently of
15 each other a Cl-C6 chain hydrocarbon group optionally
having one or more substituents selected from Group B, a
phenyl group optionally having one or more substituents
selected from Group D, a 6 membered aromatic heterocyclic
group selected from any one of Group R (the 6 membered
20 aromatic heterocyclic group may optionally have one or more
substituents selected from Group D), a 5 membered aromatic
heterocyclic group selected from any one of Group Q (the 5
membered aromatic heterocyclic group may optionally have
12 one or more substituents selected from Group D), a OR , a
C(O)OR' 25 NR'R, a NRuaRua, a NR2NR"RW, a S(O)yR, a or a 29
halogen atom,
Group R:
)N N N ND7 N-~N N R-1 R-2 R-3 R-4 R-5
N N~ N N \ N 7 N N-- N R-6 R-7 R-8 R-9 R-10
NN * N N N N'N, /N 0/ 0 0j 0 R-h1 R-12 R-13 R-14
N O N OO -- 0 N- 0 N 0
R-15 R-16 R-17
A compound of the present invention wherein q
5 represents 0, 1 or 2, and R3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
having one or more substituents selected from Group B, a 5
membered aromatic heterocyclic group selected from any one
of Group Q (the 5 membered aromatic heterocyclic group may
10 optionally have one or more substituents selected from
12 12a 1 9 11 12 Group D) , a OR', a NRIR , a NRulaRa, a NRENR R, a
S (O) yR5, or a halogen atom,
Group Q: 30
N N N N N N'N NNNN N NN 'N N -0,- \_-/ \-N \-iN
Q-1 Q-2 Q-3 Q-4 0-5 Q-6 Q-7
N N N 0 S N N
o S N N-N N-N N-0 N-N Q-8 Q-9 R Q-10 Q-11 Q-12 Q-13 Q-14
N R 2 '
N=N 0 S N 0 S N, R26 R26 0-15 0-16 Q-17 Q-18 Q-19 0-20 Q-21
{In the above formulae, R96 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms};
A compound of the present invention wherein q
5 represents 0, 1 or 2, and R3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group containing one to two
10 nitrogen atoms (the 6 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
Group D), a 5 membered aromatic heterocyclic group
containing one to four nitrogen atoms (the 5 membered
aromatic heterocyclic group may optionally have one or more
15 substituents selected from Group D), a OR, a NR'R, a
NRtNRR, a S (O) yR , or a halogen atom;
4 A compound of the present invention wherein R
3 represents a hydrogen atom, or a halogen atom; R
represents independently of each other a Cl-C6 chain 31
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
heterocyclic group containing one to two nitrogen atoms
5 (the 6 membered aromatic heterocyclic group may optionally
have one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group containing one to four
nitrogen atoms (the 5 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
10 Group D), a NRR, or a halogen atom;
A compound of the present invention wherein R'
represents a hydrogen atom, or a halogen atom; R3
represents independently of each other a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
15 atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
heterocyclic group selected from any one of the above
mentioned R-1 to R-9 (the 6 membered aromatic heterocyclic
group may optionally have one or more substituents selected
20 from Group D), a 5 membered aromatic heterocyclic group
selected from any one of the above-mentioned Q-1 to Q-7
(the 5 membered aromatic heterocyclic group may optionally
have one or more substituents selected from Group D), a
OR, a NR"R, or a halogen atom;
25 A compound of the present invention wherein R4 32
represents a hydrogen atom, or a halogen atom; R 3
represents independently of each other C1-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
5 substituents selected from Group D, a OR1 2 , or a halogen
atom;
A compound of the present invention wherein R3
represents independently of each other C1-C6 alkyl group
optionally having one or more halogen atoms, a NR11R1 2 , or a
10 halogen atom; and R" and R1 2 represent independently of
each other a hydrogen atom or a C1-C3 alkyl group
optionally having one or more halogen atoms;
A compound of the present invention wherein q
represents 0, 1 or 2, and R 3 represents independently of
15 each other a C1-C6 alkyl group optionally having one or
more halogen atoms, or a halogen atom;
A compound of the present invention wherein q
represents 0;
[0026]
20 A compound of the present invention wherein R 6
represents independently of each other a C1-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom;
A compound of the present invention wherein p
/ n 1 /I 1 1 \ .nI I 33
represents 0 or 1, and R represents a Cl-C6 alkyl group
optionally having one or more halogen atoms, a OR', a
NR R , a cyano group, a nitro group or a halogen atom;
A compound of the present invention wherein p
5 represents 0 or 1, and R represents a Cl-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom;
A compound of the present invention wherein p
represents 0;
10 [0027]
A compound of the present invention wherein R4
represents a hydrogen atom or a halogen atom, and R
represents independently of each other a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
15 atoms, a 5 membered aromatic heterocyclic group containing
1 to 4 nitrogen atoms, a NR Ra, or a halogen atom;
[0028]
A compound of the present invention wherein R4
represents a hydrogen atom or a halogen atom, R represents
20 a C2-C10 haloalkyl group, R2 represents a C2-C6 alkyl group
optionally having one or more halogen atoms, and q
represents 0, 1 or 2;
A compound of the present invention wherein
Al represents a nitrogen atom or a CH,
25 Ri represents a C2-C1O haloalkyl group, 34
R2 represents an ethyl group,
q represents 0, 1 or 2, R3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
having one or more substituents selected from Group B, a 5
5 or 6 membered aromatic heterocyclic group optionally having
one or more substituents selected from Group D, a OR, a
11 12 !lap 12a ,15, NR R , a NRu , a S(O)yR , or a halogen atom, and
R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, or
10 a halogen atom;
A compound of the present invention wherein
Al represents a nitrogen atom or a CH,
Ri represents a C2-ClO haloalkyl group,
R2 represents an ethyl group,
15 q represents 0, 1 or 2,
R represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
halogen atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
20 heterocyclic group containing 1 to 2 nitrogen atoms (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group containing 1 to 4
nitrogen atoms (the 5 membered aromatic heterocyclic group
25 may optionally have one or more substituents selected from 35
Group D) , a OR , a NR"R , a NRENR RQ, a S (O) yR1 5 , or a
hydrogen atom, and
R 6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, or
5 a halogen atom;
A compound of the present invention wherein
A2 represents a nitrogen atom or a CH;
R' represents a C2-ClO haloalkyl group;
R2 represents an ethyl group;
10 q represents 0, 1 or 2, R' represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group selected from any one
15 of the above-mentioned R-1 to R-10 (the 6 membered aromatic
heterocyclic group may optionally have one or more
substituents selected from Group D), a 5 membered aromatic
heterocyclic group selected from any one of the above
mentioned Q-1 to Q-15 (the 5 membered aromatic heterocyclic
20 group may optionally have one or more substituents selected
from Group D), a OR1 2 , a NR"R' 2 , a NRNRR' 2 , a S (0) yR 5, or
a hydrogen atom, and
R represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, or
25 a halogen atom; 36
A compound of the present invention wherein
A represents a nitrogen atom or a CH;
R' represents a C2-C10 alkyl group containing two or
more fluoro atoms;
5 R2 represents an ethyl group;
q represents 0 or 1, R3 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms or a halogen
atom; and
p represents 0;
10 A compound of the present invention wherein
Al represents a nitrogen atom or a CH;
Ri represents a C3-C6 alkyl group containing four or
more fluoro atoms,
R2 represents an ethyl group;
15 q represents 0, 1 or 2, R3 represents independently of
each other a Cl-C6 alkyl group optionally having one or
more halogen atoms, a 5 membered aromatic heterocyclic
group selected from any one of Group Q (the 5 membered
aromatic heterocyclic group may optionally have one or more
20 substituents selected from Group D), a OR, a NR"R", a
NRIaR2a or a halogen atom; and
R6 represents of independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom;
25 A compound of the present invention wherein 37
A' represents a nitrogen atom or a CH;
R represents a C3-C6 alkyl group containing four or
more fluoro atoms;
R2 represents an ethyl group;
5 q represents 0, 1 or 2, R3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group containing one to two
10 nitrogen atoms (the 6 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
Group D), a 5 membered aromatic heterocyclic group
containing 1 to 4 nitrogen atoms (the a 5 membered aromatic
heterocyclic group may optionally have one or more
15 substituents selected from Group D), a OR, a NR"R", a
NR 9NR R, a S (0) yR 5 or a halogen atom; and
R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom;
20 A compound of the present invention wherein
A' represents a nitrogen atom or a CH;
R represents a C3-C6 alkyl group containing four or
more fluoro atoms;
R2 represents an ethyl group;
25 q represents 0, 1 or 2, R3 represents independently of 38
each other a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group selected from any one
5 of the above-mentioned R-1 to R-10 (the 6 membered aromatic
heterocyclic group may optionally have one or more
substituents selected from Group D), a 5 membered aromatic
heterocyclic group selected from any one of the above
mentioned Q-1 to Q-15 (the 5 membered aromatic heterocyclic
10 group may optionally have one or more substituents selected
from Group D), a OR12, a NR"R", a NRCNRIIR±, a S(O)yR", or
a halogen atom; and
R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
15 a halogen atom;
A compound of the present invention wherein
A' represents a nitrogen atom or a CH;
R' represents a C3-C6 haloalkyl group containing 4 or
more fluoro atoms;
20 R2 represents an ethyl group;
q represents 0; and
p represents 0;
[0029]
A compound of the present invention wherein
25 R represents a C2-C10 alkyl group having one or more 39
halogen atoms, a C3-C1O alkenyl group having one or more
halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one
or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2-CS alkyl
group having one or more halogen atoms, a (Cl-CS
5 alkylsulfinyl)C2-CS alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfonyl)C2-CS alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl
group having one or more halogen atoms; R2 represents a Cl
C6 alkyl group, q represents 0 or 1; R3 represents a Cl-C6
10 alkyl group optionally having one or more halogen atoms;
and p represents 0.
[0030]
A compound represented by formula (I-A):
'R2
3 N -(R )q R 1-O R3 (I-A) N-- N (Rp
15 (hereinafter referred to as Present compound (I-A))
[wherein the symbols are the same as defined above].
[0031]
A Present compound (I-A) wherein
Ri represents a C2-ClO alkyl group having one or more
20 halogen atoms, a C3-C10 alkenyl group having one or more
halogen atoms, a (Cl-CS alkoxy)C2-C5 alkyl group having one
or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2-CS alkyl 40
group having one or more halogen atoms, a (C1-C5
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl
5 group having one or more halogen atoms; R 2 represents a C1
C6 alkyl group, q represents 0 or 1; and R3 represents
independently of each other a C1-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
10 Group D, a 6 membered aromatic heterocyclic group selected
from any one of the above-mentioned R-1 to R-9 (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group selected from any one
15 of the above-mentioned Q-1 to Q-7 (the 5 membered aromatic
heterocyclic group may optionally have one or more
substituents selected from Group D), a OR1 2 , a NR11R1 2 , or a
halogen atom; and p represents 0;
A Present compound (I-A) wherein
20 R' represents a C2-C10 alkyl group having one or more
halogen atoms, a C3-C10 alkenyl group having one or more
halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one
or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl
group having one or more halogen atoms, a (C1-C5
25 alkylsulfinyl)C2-C5 alkyl group having one or more halogen
/ n n 1 /I 1 1 \ .nI I 41
atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl
group having one or more halogen atoms; R2 represents a C1
C6 alkyl group, q represents 0 or 1; R3 represents
5 independently of each other a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
Group D, a 6 membered aromatic heterocyclic group selected
from any one of the above-mentioned R-1 to R-9 (the 6
10 membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group selected from any one
of the above-mentioned Q-1 to Q-7 (the 5 membered aromatic
heterocyclic group may optionally have one or more
15 substituents selected from Group D), a OR', a NR"R, or a
halogen atom; and p represents 0;
A Present compound (I-A) wherein
R represents a C2-C10 alkyl group having one or more
halogen atoms, a C3-C10 alkenyl group having one or more
20 halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one
or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2-C5 alkyl
group having one or more halogen atoms, a (Cl-CS
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl group having one
25 or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl 42
group having one or more halogen atoms; R2 represents a Cl
C6 alkyl group, q represents 0 or 1; R3 represents
independently of each other Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a phenyl group
5 optionally having one or more substituents selected from
Group D, a 6 membered aromatic heterocyclic group selected
from any one of the above-mentioned R-1 to R-9 (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a OR'2 , a
10 NRR, or a halogen atom; and p represents 0;
A Present compound (I-A) wherein
RI represents a C2-C10 alkyl group having one or more
halogen atoms, a C3-C10 alkenyl group having one or more
halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one
15 or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2-C5 alkyl
group having one or more halogen atoms, a (Cl-C5
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl
20 group having one or more halogen atoms; R2 represents a Cl
C6 alkyl group, q represents 0 or 1, R3 represents a Cl-C6
alkyl group optionally having one or more halogen atoms;
and p represents 0.
A Present compound (I-A) wherein
25 RI represents a C2-C10 haloalkyl group, and 43
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms;
A Present compound (I-A) wherein
R1 represents a C2-C10 haloalkyl group or a (C3-C7
5 cycloalkyl)Cl-C3 alkyl group having one or more halogen
atoms; R2 represents a Cl-C6 alkyl group; q represents 0 or
1; R 3 represents a Cl-C6 alkyl group optionally having one
or more halogen atoms; and p represents 0.
A Present compound (I-A) wherein
10 R represents a C2-C10 haloalkyl group;
R2 represents an ethyl group;
RB represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
substituents selected from Group B, a 5 or 6 membered
15 aromatic heterocyclic group optionally having one or more
substituents selected from Group D, a OR, a NRR", a
NRulaRa, a S(O)yR1 , a halogen atom; and
RP represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, or
20. a halogen atom.
A Present compound (I-A) wherein
R' represents a C2-C10 haloalkyl group;
R2 represents an ethyl group;
q represents 0, 1 or 2;
25 R3 represents independently of each other a Cl-C6 44
chain hydrocarbon group optionally having one or more
halogen atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
heterocyclic group containing one to two nitrogen atoms
5 (the 6 membered aromatic heterocyclic group may optionally
have one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group containing 1 to 4
nitrogen atoms (the 5 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
10 Group D) , a OR", a NR 1 R, a NR2 NR"R, a S(O)yR', or a
halogen atom; and
R6 represents independently of each other a C1-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom.
15 A Present compound (I-A) wherein
R represents a C2-C1O haloalkyl group;
R2 represents an ethyl group;
q represents 0, 1 or 2, R 3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
20 having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group selected from any one
of the above-mentioned R-1 to R-10 (the 6 membered aromatic
heterocyclic group may optionally have one or more
25 substituents selected from Group D), a 5 membered aromatic 45
heterocyclic group selected from any one of the above
mentioned Q-1 to Q-15 (the 5 membered aromatic heterocyclic
group may optionally have one or more substituents selected
from Group D) , a OR', a NR"R , a NR"NR"R", a S (O) yR, or
5 a halogen atom; and
R' represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom.
A Present compound (I-A) wherein
10 R represents a C2-C10 alkyl group having two or more
fluoro atoms,
R2 represents an ethyl group;
R3 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
15 a halogen atom; and
p represents 0.
A Present compound (I-A) wherein
RP represents a C3-C6 alkyl group containing four or
more fluoro atoms;
20 R2 represents an ethyl group;
R 3 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, a
5 membered aromatic heterocyclic group selected from any
one of Group Q (the 5 membered aromatic heterocyclic group
25 may optionally have one or more substituents selected from 46
Group D) , a OR", a NR'R", a NR11aR12a, or a halogen atom;
and
R, represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
5 a halogen atom.
A Present compound (I-A) wherein
R' represents a C3-C6 haloalkyl group containing 4 or
more fluoro atoms, R2 represents an ethyl group; q
represents 0; and p represents 0.
10 [0032]
A compound of the present invention wherein A
represents a CR 4 ; and R4 represents a hydrogen atom or a
halogen atom;
A compound of the present invention wherein A
15 represents a CH;
[0033]
A compound represented by formula (I-B):
2 (O)nS 'R 3 N - (R )q R 1-O /"/(I-B) N:~ 4 (R6 )p R
(hereinafter referred to as Present compound (I-B))
20 (wherein the symbols are the same as defined above.]
[00341
A Present compound (I-B) wherein 47
R represents a hydrogen atom or a halogen atom; R'
represents a C2-C10 alkyl group having one or more halogen
atoms, a C3-C1O alkenyl group having one or more halogen
atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one or more
5 halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group
having one or more halogen atoms, a (Cl-C5
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfonyl)C2-CS alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl
10 group having one or more halogen atoms; R2 represents a Cl
C6 alkyl group; q represents 0 or 1; R3 represents
independently of each other a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
15 Group D, a 6 membered aromatic heterocyclic group selected
from any one of the above-mentioned R-1 to R-9 (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group selected from any one
20 of the above-mentioned Q-1 to Q-7 (the 5 membered aromatic
heterocyclic group may optionally have one or more
Op12, 1R2 12 substituents selected from Group D), a OR , a NR"R , or a
halogen atom; and p represents 0;
A Present compound (I-B) wherein
25 R4 represents a hydrogen atom or a halogen atom; R' 48
represents a C2-CIO alkyl group having one or more halogen
atoms, a C3-C10 alkenyl group having one or more halogen
atoms, a (Cl-C5 alkoxy)C2-CS alkyl group having one or more
halogen atoms, a (Cl-CS alkylsulfanyl)C2-CS alkyl group
5 having one or more halogen atoms, a (Cl-C5
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-CS alkylsulfonyl)C2-CS alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl
group having one or more halogen atoms; R2 represents a Cl
10 C6 alkyl group; q represents 0 or 1; R3 represents a Cl-C6
alkyl group; q represents 0 or 1; R3 represents
independently of each other a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
15 Group D, a 6 membered aromatic heterocyclic group selected
from any one of the above-mentioned R-1 to R-9 (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a OR 2, a
NR R, or a halogen atom; and p represents 0;
20 A Present compound (I-B) wherein
R4 represents a hydrogen atom or a halogen atom; R
represents a C2-C10 alkyl group having one or more halogen
atoms, a C3-C1O alkenyl group having one or more halogen
atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one or more
25 halogen atoms, a (Cl-CS alkylsulfanyl)C2-C5 alkyl group 49
having one or more halogen atoms, a (Cl-CS
alkylsulfinyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-CS alkylsulfonyl)C2-C5 alkyl group having one
or more halogen atoms, or a (C3-C7 cycloalkyl)Cl-C3 alkyl
5 group having one or more halogen atoms; R2 represents a C1
C6 alkyl group; q represents 0 or 1; R3 represents a Cl-C6
alkyl group optionally having one or more halogen atoms;
and p represents 0.
A Present compound (I-B) wherein
10 R4 represents a hydrogen atom or a halogen atom;
R represents a C2-C10 haloalkyl group; and
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms.
A Present compound (I-B) wherein
15 R represents a C2-C10 haloalkyl group; q represents 0
or 1; R3 represents a C1-C6 alkyl group optionally having
one or more halogen atoms; and p represents 0.
A Present compound (I-B) wherein
R4 represents a hydrogen atom or a halogen atom;
20 R represent a C2-C10 haloalkyl group;
R represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
substituents selected from Group B, a 5 or 6 membered
aromatic heterocyclic group optionally having one or more
25 substituents selected from Group D, a OR, a NR"R, a 50
NPua1ua, a S (O) yR, or a halogen atom; and
R' represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom.
5 A Present compound (I-B) wherein
R4 represents a hydrogen atom or a halogen atom;
R represents a C2-C0 haloalkyl group;
R represents an ethyl group;
q represents 0, 1 or 2, R represents independently of
10 each other a CI-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group containing one to two
nitrogen atoms (the 6 membered aromatic heterocyclic group
15 may optionally have one or more substituents selected from
Group D), a 5 membered aromatic heterocyclic group
containing 1 to 4 nitrogen atoms (the 5 membered aromatic
heterocyclic group may optionally have one or more
substituents selected from Group D), a OR, a NR R, a
20 NR2R R, a S (O) yR', or a halogen atom; and
R represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a hydrogen atom.
A Present compound (I-B) wherein
25 R 4 represents a hydrogen atom or a halogen atom; 51
RI represents a C2-C10 haloalkyl group;
R2 represents an ethyl group;
q represents 0, 1 or 2, R3 represents independently of
each other a Cl-C6 chain hydrocarbon group optionally
5 having one or more halogen atoms, a phenyl group optionally
having one or more substituents selected from Group D, a 6
membered aromatic heterocyclic group selected from any one
of the above-mentioned R-1 to R-10 (the 6 membered aromatic
heterocyclic group may optionally have one or more
10 substituents selected from Group D), a 5 membered aromatic
heterocyclic group selected from any one of the above
mentioned Q-1 to Q-15 (the 5 membered aromatic heterocyclic
group may optionally have one or more substituents selected
from Group D), a OR 1 2 , a NR"R", a NR2 9R'R1, a S (0) yR5, or a
15 halogen atom; and
Rs represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a halogen atom.
A Present compound (I-B) wherein
20 R 4 represents a hydrogen atom;
R represents a C2-C10 alkyl group having two or more
fluoro atoms;
R2 represents an ethyl group;
R' represents independently of each other a Cl-C6
25 alkyl group optionally having one or more halogen atoms or 52
a halogen atom; and
p represents 0.
A Present compound (I-B) wherein
R4 represents a hydrogen atom;
5 Ri represents a C3-C6 alkyl group containing four or
more fluoro atoms;
R 2 represents an ethyl group;
R3 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms, a
10 5 membered aromatic heterocyclic group selected from any
one of Group Q (the 5 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
Group D), a OR2, a NR' 1 R' 2 , a NRuaRd12a, or a hydrogen atom;
and
15 R6 represents independently of each other a Cl-C6
alkyl group optionally having one or more halogen atoms or
a hydrogen atom.
A Present compound (I-B) wherein
R' represents a C3-C6 haloalkyl group containing 4 or
20 more fluoro atoms;
R represents an ethyl group;
q represents 1, R3 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms; and
p represents 0.
25 [0035] 53
Next, a process for preparing the compound of the
present invention is explained.
[00361
The compound of the present invention can be prepared,
5 for example, according to the following processes.
[0037]
Process 1
A compound represented by formula (Ib) (hereinafter,
referred to as Present compound (Ib)) and a compound
10 represented by formula (Ic) (hereinafter, referred to as
Present compound (Ic)) may be prepared by reacting a
compound represented by formula (Ia) (hereinafter, referred
to as Present compound (Ia)) with an oxidizing agent.
R2 R2 S (O)S N N 3 R1-O (R/R-O(R
( ) )q(R(R)) (la) (Ib)
/R2 (0)2S N 3_ R 1-O (Ra
(R6 (Ic)
15 [wherein the symbols are the same as defined above]
[00381
First, a process for preparing the Present compound
/ n A 1 1 1\ .nI I 54
(Ib) from the Present compound (Ia) is described.
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
halogenated aliphatic hydrocarbons such as dichloromethane
5 and chloroform (hereinafter, collectively referred to as
halogenated aliphatic hydrocarbons); nitriles such as
acetonitrile (hereinafter collectively referred to
nitriles); esters such as ethyl acetate (hereinafter
collectively referred to esters); alcohols such as methanol
10 and ethanol (hereinafter, collectively referred to as
alcohols); acetic acid; water; and mixed solvents thereof.
Examples of the oxidizing agent to be used in the
reaction includes sodium periodate, m-chloroperoxybenzoic
acid (hereinafter referred to as mCPBA), and hydrogen
15 peroxide.
When hydrogen peroxide is used as the oxidizing agent,
sodium carbonate or a catalyst may be added as needed.
Examples of the catalyst to be used in the reaction
include tungstic acid, and sodium tungstate.
20 In the reaction, the oxidizing agent is used usually within a
range of 1 to 1.2 molar ratio(s), the sodium carbonate is used
usually within a range of 0.01 to 1 molar ratio(s), and the catalyst
is used usually within a range of 0.01 to 0.5 molar ratios, as
opposed to 1 mole of the Present compound (Ia).
/ n n 1 /I 1 1 \ .nI I 55
The reaction temperature of the reaction is usually
within a range of -20 to 80°C. The reaction period of the
reaction is usually within a range of 0.1 to 12 hours.
When the reaction is completed, to the reaction
5 mixtures is added water, and the reaction mixtures are then
extracted with organic solvent(s), and the organic layers
are washed successively with an aqueous solution of a
reducing agent (such as sodium sulfite, and sodium
thiosulfate) and an aqueous solution of a base (such as
10 sodium hydrogen carbonate). The resulting organic layers
are dried and concentrated to give the Present compound
(Tb).
[0039]
Next, a process for preparing the Present compound
15 (Ic) from the Present compound (Ib) is explained.
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
halogenated aliphatic hydrocarbons, nitriles, alcohols,
acetic acid, water, and mixed solvents thereof.
20 Examples of the oxidizing agent to be used in the
reaction include mCPBA and hydrogen peroxide. When
hydrogen peroxide is used as oxidizing agent, a base or a
catalyst may be added as needed.
Examples of the base to be used include sodium
25 carbonate. 56
Examples of the catalyst to be used include sodium
tungstate.
In the reaction, the oxidizing agent is used usually
within a range of 1 to 2 molar ratio(s), the base is used
5 usually within a range of 0.01 to 1 molar ratio(s), and the
catalyst is used usually within a range of 0.01 to 0.5
molar ratios, as opposed to 1 mole of the Present compound
(Ib).
The reaction temperature of the reaction is usually
10 within a range of -20 to 120°C. The reaction period of the
reaction is usually within a range of 0.1 to 12 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvent(s), and the organic layers
15 are washed successively with an aqueous solution of a
reducing agent (such as sodium sulfite, and sodium
thiosulfate) and an aqueous solution of a base (such as
sodium hydrogen carbonate). The resulting organic layers
are dried and concentrated to give the Present compound
20 (Ic).
[0040]
Also, the Present compound (Ic) may be prepared in one
step (one-spot) by reacting the Present compound (Ia) with
an oxidizing agent.
25 The reaction may be carried out by using the oxidizing 57
agent usually in 2.0 to 2.4 molar ratios as opposed to 1
mole of the Present compound (Ia) according to the method
for preparing the Present compound (Tc) from the Present
compound (Ib).
5 [0041]
Process 2
The compound of the present invention represented by
formula (I) (hereinafter referred to as Present compound
(I)) may be prepared by reacting a compound represented by
10 formula (M-3) (hereinafter referred to as Compound (M-3))
with a compound represented by formula (R-3) (hereinafter,
referred to as Compound (R-3)) in the presence of a base.
R 2 R 2 (O)nS (O)"S
N (Iq (-)N R) H-O /R3 R 1-O (/R
(R6)p (R)p
(M-3) (1)
[wherein V represents a halogen atom, a
15 trifluoromethansulfonyloxy group, a
nonafluorobutanesulfonyloxy group, or a tosyloxy group, and
the other symbols are the same as defined above.]
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
20 ethers such as tetrahydrofuran (hereinafter, referred to as
THF), ethyleneglycol dimethyl ether, methyl tert-butyl 58
ether, and 1,4-dioxane (hereinafter, collectively referred
to as ethers); halogenated aliphatic hydrocarbons; aromatic
hydrocarbons such as toluene and xylene (hereinafter,
collectively referred to as aromatic hydrocarbons); polar
5 aprotic solvents such as dimethylformamide (hereinafter,
referred to as DMF), N-methyl pyrrolidone (hereinafter,
referred to as NMP), dimethyl sulfoxide (hereinafter,
referred to DMSO) (hereinafter, collectively referred to as
polar aprotic solvent); and mixed solvents thereof.
10 Examples of the base to be used in the reaction
include organic bases such as triethylamine,
diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine
(hereinafter, collectively referred to as organic bases);
alkali metal hydrides such as sodium hydride (hereinafter,
15 collectively referred to as alkali metal hydrides); and
alkali metal carbonates such as sodium carbonate and
potassium carbonate (hereinafter, referred to as alkali
metal carbonates).
In the reaction, the compound (R-3) is usually used
20 within a range of in 1 to 10 molar ratio(s), and the base
is usually used within a range of 0.1 to 5 molar ratio(s),
as opposed to 1 mole of the compound (M-3).
The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
25 usually within a range of 0.5 to 24 hours. 59
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the resulting organic
layers are worked up (for example, drying and
5 concentration) to give the Present compound (I).
[0042]
Process 3
The Present compound (Ia) may be prepared by reacting
a compound represented by formula (M-1) (hereinafter,
10 referred to Compound (M-1)) with a compound represented by
formula (R-1) (hereinafter, referred to Compound (R-1)) in
the presence of a base.
R 2-SH S
R-O (R3)gq (R-1) , NR-O(R 3)q N A-/ R'-O r0~
(M-1) (la)
[wherein V 2 represents a halogen atom, and the other
15 symbols are the same as defined above.]
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aromatic hydrocarbons, nitriles, polar aprotic
solvents, and mixed solvents thereof.
20 Examples of the base to be used in the reaction
include alkali metal carbonates and alkali metal hydrides. 60
In the reaction, the compound (R-1) is used usually
within a range of 1 to 10 molar ratio(s), and the base is
used usually within a range of 1 to 10 molar ratio(s), as
opposed to 1 mole of the compound (M-1).
5 The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
usually within a range of 0.5 to 24 hours.
When the reaction is completed, the reaction mixtures
are extracted with organic solvents, and the resulting
10 organic layers are worked up (for example, drying and
concentration) to give the Present compound (Ia).
V2 is preferably a fluorine atom or a chlorine atom.
[0043]
Process 4
15 The Present compound (I) may be prepared by reacting a
compound represented by formula (M-4) (hereinafter,
referred to as Compound (M-4)) with a compound represented
by formula (R-4) (hereinafter, referred to as Compound (R
4)) in the presence of a base.
R2 R 2 (O)nS R'-OH (0)nS N (R3), (R-4) N (R3) N7 ~~ R\~ 6/ A'N6pA
(R (R 20 (M-4) (1)
[wherein the symbols are the same as defined above.] 61
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aromatic hydrocarbons, nitriles, polar aprotic
solvent, and mixed solvents thereof.
5 Examples of the base to be used in the reaction
include alkali metal carbonates and alkali metal hydrides.
In the reaction, the compound (R-4) is usually used
within a range of 1 to 10 molar ratio(s), and the base is
usually used within a range of 1 to 10 molar ratio(s), as
10 opposed to 1 mole of the compound (M-4).
The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
usually within a range of 0.5 to 24 hours.
When the reaction is completed, to the reaction
15 mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the resulting organic
layers are worked up (for example, drying and
concentration) to give the Present compound (I).
V is preferably a fluorine atom.
20 [0044]
Process 5
A compound represented by formula (Ig) (hereinafter,
referred to as Present compound (Ig)) may be prepared
according to a method described below. 62
35 0 NR2 R CH 3 R2 o- R37o W ONS N R N/CH N R-O ( CI NH3 , R-O R
(R6), (%s (M-7) (g)
[wherein R37 represents a Cl-C6 alkyl group, R35 represents
a hydrogen atom, a Cl-C6 alkyl group optionally having one
or more halogen atoms, a phenyl group optionally having one
5 or more substituents selected from Group D, or a 5 or 6
membered aromatic heterocyclic group optionally having one
or more substituents selected from Group D, and the other
symbols are the same as defined above.]
[00451
10 First, Step 1 is explained.
In the Step 1, a compound represented by formula (M-7)
(hereinafter, referred to as Compound (M-7)) and a compound
represented by formula (R-7) (hereinafter, referred to as
Compound (R-7)) are reacted.
15 The compound (R-7) may be prepared according to a
similar method to that described in International
Publication No. 2009/054742.
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
20 ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, alcohols, esters,
nitriles, polar aprotic solvent, nitrogen-containing 63
aromatic compounds such as pyridine and 2,6-lutidine
(hereinafter, collectively referred to as nitrogen
containing aromatic compounds), and mixed solvents thereof.
A base may be added to the reaction, and examples of
5 the base include organic bases.
In the reaction, the compound (R-7) is usually used
within a range of 1 to 10 molar ratio(s), and the base is
usually used within a range of 1 to 10 molar ratio(s), as
opposed to 1 mole of the compound (M-7)).
10 The reaction temperature is usually within a range of
-50 to 200°C. The reaction period of the reaction is
usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures
are concentrated to obtain the residues, which are used as
15 itself in the Step 2. Alternatively, to the reaction
mixtures are added water and the mixtures are then
extracted with organic solvents, and the organic layers are
worked (for example, drying and concentration) to obtain
the residues, which are used in the Step 2.
20 [0046]
Next, Step 2 is explained.
In the Step 2, the residue obtained in the step 1 is
reacted with ammonia to give the Present compound (Ig).
The reaction is usually carried out in a solvent.
25 Examples of the solvent to be used in the reaction 64
include ethers, nitriles, alcohols, polar aprotic solvent,
nitrogen-containing aromatic compounds, and mixed solvents
thereof.
Examples of the ammonia to be used in the reaction
5 include aqueous ammonia solution and solution of ammonia in
methanol.
In the reaction, ammonia is usually used within a
range of 1 to 100 molar ratio(s) as opposed to 1 mole of
the compound (M-7).
10 The reaction temperature is usually within a range of
0 to 100°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the resulting mixtures are
15 extracted with organic solvents, and the organic layers are
worked up (for example, drying and concentration) to give
the Present compound (Ig).
[00471
Process 6
20 A compound represented by formula (Id) (hereinafter,
referred to as Present compound (Id)), a compound
represented by formula (Ie) (hereinafter, referred to
Present compound (Ie)), a compound represented by formula
(If) (hereinafter, referred to Present compound (If)), and
25 a compound represented by formula (Im) (hereinafter, 65
referred to Present compound (Im) may be prepared by
reacting the Present compound (Ic) with an oxidizing agent.
R2 R2 R2 (O)2S 0- (O)2S' o-(O)2s
RiO N(3R'-O (3 +R'-O0 (R3)q
t 1R/ /(R )p (RR)%R (e) -(Id) (le)
R2 R2
(O)2S (0)2S
3 -(R3) + R'O / (R ), + R-O N Nt / ~ ' R) (R6), (if) (im)
[wherein the symbols are the same as defined above.]
5 [0048]
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
halogenated aliphatic hydrocarbons; nitriles; esters such
as ethyl acetate; alcohols; acetic acid; water; and mixed
10 solvents thereof.
Examples of the oxidizing agent to be used in the
reaction include mCPBA and hydrogen peroxide.
When hydrogen peroxide is used as the oxidizing agent,
an acid, a base or a catalyst may be added as needed.
15 Examples of the acid to be used in the reaction
include acetic acid, sulfuric acid, and trifluoroacetic
acid.
Examples of the base to be used include sodium 66
carbonate.
Examples of the catalyst to be used include tungstic
acid and sodium tungstate.
In the reaction, the oxidizing agent is used usually
5 within a range of 1 to 10 molar ratio(s), the acid is used
usually within a range of 0.01 to 1 molar ratio(s), the
base is used usually within a range of 0.01 to 1 molar
ratio(s), and the catalyst is used usually within a range
of 0.01 to 0.5 molar ratio(s), as opposed to 1 mole of the
10 Present compound (Ic).
The reaction temperature of the reaction is usually
within a range of -20 to 80°C. The reaction period of the
reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, to the reaction
15 mixtures is added water, and the reaction mixtures are then
extracted with organic solvent(s), and the organic layers
are washed with an aqueous solution of a reducing agent
(such as sodium sulfite, and sodium thiosulfate) and an
aqueous solution of a base (such as sodium hydrogen
20 carbonate). The resulting organic layers are dried and
concentrated to give the residues, and the resulting
residues are worked up (such as chromatography or
recrystallization) to isolate the Present compound (Id),
the Present compound (Ie) and the Present compound (If), or
25 the Present compound (Im) respectively. 67
[0049]
Process 7
The Present compound (Ia) may be prepared by reacting
a compound represented by formula (M-2) (hereinafter,
5 referred to as Compound (M-2)) with a compound represented
by formula (R-2) (hereinafter, referred to as Compound (R
2)) in the presence of a base.
IR2 HS S N) N RN-O (R3 (-R (R3) N- A 1 / R N/':) (R6)p (R6)
(M-2) (la)
[wherein the symbols are the same as defined above.]
10 The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aromatic hydrocarbons, nitriles, and polar aprotic
solvent.
Examples of the base to be used in the reaction
15 include alkali metal carbonates and alkali metal hydrides.
In the reaction, the compound (R-2) is usually used
within a range of in 1 to 10 molar ratio(s), and the base
is usually used within a range of 1 to 10 molar ratio(s),
as opposed to 1 mole of the compound (M-2). Preferably,
20 the compound (R-2) is usually used within a range of in 1.0
to 1.1 molar ratio(s), and the base is usually used within 68
a range of 1 to 2 molar ratio(s), as opposed to 1 mole of
the compound (M-2).
The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
5 usually within a range of 0.5 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the resulting organic
layers are worked up (for example, drying and
10 concentration) to give the Present compound (Ia).
[0050]
Process 8
A compound represented by formula (Ik) (hereinafter,
referred to as Present compound (Ik)) may be prepared
15 according to a method described below.
IR2 (Q) S R3
R M/ R R'-O N2 HN 3 36 R2 R 5 R ( (O)"S R R lyR6(), R60)SIR R33 ( (M-22a) () R
R-O /N (R-5) + - Rt-O R s N NH 2 R Nz N (R6 R6 (R6), (O)"S R3 3 5 (M-20) R -N R (1k) NW HN R3
(R 6 ORv (M-22b)
[wherein R34 and R r epresent independently of each other a
hydrogen atom, a Cl-C6 alkyl group optionally having one or 69
more halogen atoms, a phenyl group optionally having one or
more substituents selected from Group D, or a 5 or 6
membered aromatic heterocyclic group optionally having one
or more substituents selected from Group D; R represents a
5 hydrogen atom, or a C1-C4 alkyl group; and the other
symbols are the same as defined above.]
[0051]
First, Step 1 is explained.
In the Step 1, a compound represented by formula (M
10 20) (hereinafter, referred to as Compound (M-20)) and a
compound represented by formula (R-5) (hereinafter,
referred to as Compound (R-5)) are reacted to give a
compound represented by formula (M-22a) (hereinafter,
referred to as Compound (M-22a)) and a compound represented
15 by formula (M-22b) (hereinafter, referred to as Compound
(M-22b)).
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
20 halogenated aliphatic hydrocarbons, alcohols, esters,
nitriles, polar aprotic solvent, nitrogen-containing
aromatic compounds, and mixed solvents thereof.
An acid or a base may be added to the reaction as
needed. Examples of the acid to be used in the reaction
25 include carbonic acids such as acetic acid; and sulfonic 70
acids such as methanesulfonic acid and p-toluenesulfonic
acid, and examples of the base to be used in the reaction
include alkali metal carbonates, alkali metal hydrides, and
organic bases.
5 In the reaction, the compound (R-5) is usually used
within a range of 1 to 10 molar ratio(s), and the base is
usually used within a range of 0.1 to 10 molar ratio(s), as
opposed to 1 mole of the compound (M-20).
The reaction temperature is usually within a range of
10 0 to 200 0 C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the reaction mixtures
15 are worked up (for example, drying and concentration) to
give the Present compound (M-22a), the Present compound (M
22b), or a mixture thereof.
[0052]
Next, Step 2 is described.
20 In the Step 2, the compound (M-22a), the compound (M
22b) or the mixture thereof is reacted with an oxidizing
agent to give Present compound (Ik).
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
25 ethers, aliphatic hydrocarbons, aromatic hydrocarbons, 71
halogenated aliphatic hydrocarbons, nitriles, polar aprotic
solvent, nitrogen-containing aromatic compounds, and mixed
solvents thereof.
Examples of the oxidizing agent to be used in the
5 reaction include manganese dioxide.
Instead of using the oxidizing agent, the compound (M
22a), the compound (M-22b) or the mixture thereof may be
reacted with methanesulfonyl chloride and triethylamine
successively, or the mixture of methanesulfonyl chloride
10 and triethylamine.
Instead of using the oxidizing agent, the compound (M
22a), the compound (M-22b) or the mixture thereof may be
reacted with Pd-C and olefins such as vinyl acetate
successively, or the mixture of Pd-C and vinyl acetate.
15 In the reaction, the oxidizing agent is usually used
within a range of 1 to 10 molar ratio(s) as opposed to 1
mole of the compound (M-22a) or the compound (M-22b).
In the reaction, when methanesulfonyl chloride and
triethylamine are used instead of the oxidizing agent, the
20 methanesulfonyl chloride is usually used within a range of
1 to 10 molar ratio(s), and the triethylamine is usually
used within a range of 1 to 10 molar ratio(s), as opposed
to 1 mole of the compound (M-22a) or the compound (M-22b).
In the reaction, when Pd-C and olefins such as vinyl
25 acetate are used instead of the oxidizing agent, the Pd-C 72
is usually used within a range of 0.001 to 1 molar ratio(s),
and the olefins is usually used within a range of 1 to 10
molar ratio(s), as opposed to 1 mole of the compound (M
22a) or the compound (M-22b).
5 The reaction temperature is usually within a range of
0 to 200°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed,
to the reaction mixtures is added water, and the reaction
10 mixtures are then extracted with organic solvents, and the
organic layers are worked up (for example, drying and
concentration) to isolate the Present compound (Ik).
[0053]
Process 9
15 A compound represented by formula (Ii) (hereinafter,
referred to as Present compound (Ii)) may be prepared
according to a method described below. 73
R35 ,R2 R34 CI ,R2 34 (O)RSt(O)~O 0 (O)nS R R N (R-6) N
N NH 2 N HN 0 (R)p (RM)p 2 (M-20) (M-21)
().S R34 R'-O Ra
N: N OH (R6)P (li)
[wherein the symbols are the same as defined above.]
First, the process for preparing the compound
represented by formula (M-21) (hereinafter, referred to as
5 Compound (M-21)) from the compound (M-20) is described.
The compound (M-21) may be prepared by reacting the
compound (M-20) with a compound represented by formula (R
6) (hereinafter, referred to as Compound (R-6)).
The reaction is usually carried out in a solvent.
10 Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, nitriles, polar aprotic
solvent, nitrogen-containing aromatic compounds, and mixed
solvents thereof.
15 In the reaction, the compound (R-6) is usually used
within a range of 1 to 10 molar ratio(s) as opposed to 1 74
mole of the compound (M-20).
The reaction temperature is usually within a range of
0 to 200°C. The reaction period.of the reaction is usually
within a range of 0.1 to 24 hours.
5 When the reaction is completed, to the reaction
mixtures is added water, and the resulting mixtures are
then extracted with organic solvents, and the organic
layers are worked up (for example, drying and
concentration) to isolate the compound (M-21).
10 [0054]
Next, the process for preparing the Present compound
(Ii) from the compound (M-21) is described.
The Present compound (Ii) may be prepared by reacting
the compound (M-21) with a halogenating agent.
15 The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, nitriles, polar aprotic
solvent, nitrogen-containing aromatic compounds, and mixed
20 solvents thereof.
Examples of the halogenating agent to be used in the
reaction include N-bromosuccinimide, N-chlorosuccinimide,
sulfuryl chloride, and bromine.
A catalyst may be added to the reaction as needed.
25 Examples of the catalyst to be used in the reaction include 75
benzoyl peroxide.
In the reaction, a halogenating agent is usually used
within a range of 1 to 10 molar ratio(s), and the catalyst
is usually used within a range of 0.1 to 0.5 molar ratio(s),
5 as opposed to 1 mole of the compound (M-21).
The reaction temperature is usually within a range of
0 to 200°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed, to the reaction
10 mixtures is added water, and the resulting mixtures are
then extracted with organic solvents, and the organic
layers are worked up (for example, drying and
concentration) to isolate the Present compound (Ii).
[0055]
15 Process 10
A compound represented by formula (Ij) (hereinafter,
referred to as Present compound (Ij)) may be prepared by
reacting the compound (M-20) with a compound represented by
formula (R-8) (hereinafter, referred to as Compound (R-8)).
Ra35 R2 R37o R-36 R2
/N (R-8) O RN R1 - 0 R'-O /0/ R3 5
Na- NH 2 N N~ (R6)p (R(R% (R)p R 36
20 (M-20) (j) [wherein, the symbols are the same as defined above.] 76
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, nitriles, alcohols,
5 polar aprotic solvent, nitrogen-containing aromatic
compounds, and mixed solvents thereof.
In the reaction, the compound (R-8) is usually used
within a range of 1 to 10 molar ratio(s) as opposed to 1
mole of the compound (M-20)).
10 The reaction temperature is usually within a range of
0 to 200°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the resulting mixtures are
15 then extracted with organic solvents, and the organic
layers are worked up (for example, drying and
concentration) to isolate the Present compound (Ij).
[00561
Process 11
20 A compound represented by formula (Ik) (hereinafter,
referred to as Present compound (Ik)) may be prepared
according to a method described below. 77
R35
(O)"SR2 R3 R3s (O)nS 2 R34 N (R-5) O N O
N¾ 0 N O R3 5 R 36
(R6), (R6)p (M-7) (M-23)
34 3 (O)nS R (O)nS R 4 (0)'S R 34 N /10N aN R R35 W_ HN R N=_ HN R 36 N
OR(RN)p (R6k
(M-22a) (M-22b) (1k)
[wherein, the symbols are the same as defined above.]
[0057]
First, Step 1 is explained.
5 In the Step 1, a compound represented by formula (M-7)
(hereinafter, referred to as Compound (M-7)) and a compound
represented by formula (R-5) (hereinafter, referred to as
Compound (R-5)) are reacted to give a compound represented
by formula (M-23) (hereinafter, referred to as Compound (M
10 23)).
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, alcohols, esters,
15 nitriles, polar aprotic solvent, nitrogen-containing
aromatic compounds, and mixed solvents thereof. 78
In the reaction, the compound (R-5) is usually used
within a range of 1 to 10 molar ratio(s) as opposed to 1
mole of the compound (M-7)).
The reaction temperature is usually within a range of
5 C to 200°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures
are worked up (for example, drying and concentration) to
isolate the compound (M-23). Alternatively, when the
10 reaction is completed, the resulting compound (M-23) is not
isolated and is used as itself in Step 2, or the reaction
mixtures are concentrated to obtain the residues, which are
used as itself in the Step 2.
[0058]
15 Next, Step 2 is described.
In the Step 2, the compound (M-23) is reacted with
ammonia to give the compound (M-22a) and the compound (M
22b).
The reaction is usually carried out in a solvent.
20 Examples of the solvent to be used in the reaction include
ethers, aliphatic hydrocarbons, aromatic hydrocarbons,
halogenated aliphatic hydrocarbons, alcohols, enters,
nitriles, polar aprotic solvent, nitrogen-containing
aromatic compounds, and mixed solvents thereof.
25 Examples of the ammonia to be used in the reaction 79
include aqueous ammonia solution and solution of ammonia in
methanol.
The ammonia to be used in the reaction may be in the
form of a gas, or may be in the form of an aqueous solution
5 or an alcoholic solution. Alternatively, ammonium
carboxylate such as ammonium acetate; ammonium phosphate
such as ammonium dihydrogenphosphate; ammonium carbonate;
ammonium halides such as ammonium chloride may be used.
In the reaction, ammonia is usually used within a
10 range of 1 to 10 molar ratio(s) as opposed to I mole of the
compound (M-7).
The reaction temperature is usually within a range of
0 to 200°C. The reaction period of the reaction is usually
within a range of 0.1 to 24 hours.
15 When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
worked up (for example, drying and concentration) to give
the compound (M-22a), the compound (M-22b) or the mixture
20 thereof. Alternatively, when the reaction is completed,
the resulting compound (M-22a), the resulting compound (M
22b) or the resulting mixture thereof is not isolated and
is used as itself in Step 3, or the reaction mixtures are
concentrated to obtain the residues, which are used as
25 itself in the Step 3. 80
[0059]
Next, Step 3 is described.
In the Step 3, the compound (M-22a), the compound (M
22b), or the mixture thereof may be reacted with an
5 oxidizing agent according to the method described in the
Step 2 of the Process 8 to prepare the Present compound
(Ik).
[0060]
Hereinafter, a process for preparing each intermediate
10 compound is described.
[0061]
Reference Process I
The compound (M-1) may be prepared by reacting a
compound represented by formula (M-8) (hereinafter,
15 referred to Compound (M-8)) with a compound represented by
formula (M-9) (hereinafter, referred to Compound (M-9)) in
the presence of a metal catalyst.
2 V 2 V
3 (R3)q R0+ (R )q R-O /N N 3 NA' (RII)p (R6), (M-8) (M-9) (M-1)
[wherein V3 represents a chlorine atom, a bromine atom or
20 an iodine atom; M represents 9-borabicyclo[3.3.lnona-9-yl
group, -B(OH) 2, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl
group, Sn(n-C 4H9 ) 3 , ZnCl, MgI, or MgBr; and the other 81
symbols are the same as defined above.]
The compound (M-9) may be prepared according to a
similar method to that described in International
Publication 03/024961 or Organic Process Research &
5 Development, 2004, 8, 192-200.
The compound (M-8) may be prepared according to a
similar method to that described in International
Publication 2010/016005.
The reaction is usually carried out in a solvent.
10 Examples of the solvent to be used in the reaction include
ethers, aromatic hydrocarbons, polar aprotic solvent, water,
and mixed solvents thereof.
Examples of the metal catalyst to be used in the
reaction include palladium catalysts such as
15 tetrakis(triphenylphosphine)palladium(0), 1,1'
bis(diphenylphosphino)ferrocene palladium(II) dichloride,
tris(dibenzylideneacetone)dipalladium(0), and palladium(II)
acetate; nickel catalysts such as
bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and
20 copper catalyst such as copper(I) iodide and copper(I)
chloride.
A ligand, a base and/or an inorganic halogenated
compound may be added to the reaction as needed.
Examples of the ligand to be used in the reaction
25 include triphenylphosphine, Xantphos, 2,2'- 82
bis(diphenylphoshino)-1,1'-binaphthyl, 1,1'
bis(diphenylphoshino)ferrocene, 2-(dicyclohexylphosphino)
2',4',6'-triisopropyl-1,1'-biphenyl, 2
dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2
5 bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2
aminoethanol, 8-hydroquinoline, and 1,10-phenanthroline.
Examples of the base to be used in the reaction
include alkali metal hydrides, alkali metal carbonates, and
organic bases.
10 Examples of the inorganic halogenated compounds
include alkali metal fluorides such as potassium fluoride,
and sodium fluoride; and alkali metal chlorides such as
lithium chloride, and sodium chloride.
In the reaction, the compound (M-9) is usually used
15 within a range of 1 to 10 molar ratio(s), the metal
catalyst is usually used within a range of 0.01 to 0.5
molar ratios, the ligand is usually used within a range of
0.01 to I molar ratio(s), the base is usually used within a
range of 0.1 to 5 molar ratios, and the inorganic
20 halogenated compound is usually used within a range of 0.1
to 5 molar ratios, as opposed to 1 mole of the compound (M
8).
The reaction temperature is usually within a range of
-20 to 200°C. The reaction period of the reaction is
25 usually within a range of 0.1 to 24 hours. 83
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvent(s), and the organic solvents
are worked up (for example, drying and concentration) to
5 give the compound (M-l).
[0062]
Reference Process 2
The compound (M-3) may be prepared by reacting a
compound represented by formula (M-ll) (hereinafter,
10 referred to as Compound (M-11)) with an acid.
R 2 R 2 (O)"S (O)nS (R3) R (R3)- H-O N
(R6)p ( ), (M-11) (M-3) [wherein, R' represents a methyl group or an ethyl group;
and the other symbols are the same as defined above.]
The reaction is usually carried out in a solvent.
15 Examples of a solvent to be used in the reaction include
halogenated aliphatic hydrocarbons, aromatic hydrocarbons,
nitriles, alcohols, acetic acid, water, and mixed solvents
thereof.
Examples of the acid to be used in the reaction
20 include mineral acids such as hydrochloric acid; boron
halides such as boron trichloride and boron tribromide;
metal chlorides such as titanium chloride, and aluminium 84
chloride.
In the reaction, the acid is usually used within a
range of 0.1 to 10 molar ratio(s) as opposed to 1 mole of
the compound (M-11). In the reaction, when the mineral
5 acids are used as an acid, the mineral acid may be used
also as a solvent.
The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
usually within a range of 0.1 to 24 hours.
10 When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
worked up (for example, drying and concentration) to give
the compound (M-3).
15 [0063]
Reference Process 3
The compound (M-11) wherein n is 0 (hereinafter,
referred to as Compound (M-11a)), the compound (M-11)
wherein n is 1 (hereinafter, referred to as Compound (M
20 l1b)), and the compound (M-11) wherein n is 2 (hereinafter,
referred to as Compound (M-11c)) may be prepared according
to a method described below. 85
V 2 V2
(R(Rq ((RR 3 Rx-O0 V + M N:\ >7 Nt A'JN1_
(M-12) (M-9) {M-13)
2 0N -R2 R R2
3 3 Rx-O (R )q RN-0 (R Rx-O N
)qRq (3) (R6)p (R6)p (Re)p (M-11c) (M-11b) (M-11a)
[wherein the symbols are the same as defined above.]
A compound represented by formula (M-13) (hereinafter,
referred to as Compound (M-13)) may be prepared by using a
5 compound represented by formula (M-12) (hereinafter,
referred to as Compound (M-12)) instead of the compound (M
8) according to the similar method to that described in
Reference Process 1.
The compound (M-12) is a commercially available
10 compound, or may be prepared according to the similar
method to a well-known method.
The compound (M-11a) may be prepared by using the
compound (M-13) instead of the compound (M-1) according to
a method described in Process 3.
15 The compound (M-11b) and the compound (M-11c) may be
prepared by using the compound (M-11a) instead of the
compound (Ia) according to the similar method to that 86
described in Process 1.
[ 0064]
Reference Process 4
A compound represented by formula (M-17) (hereinafter,
5 referred to as Compound (M-17)) may be prepared by reacting
a compound represented by formula (M-16) (hereinafter,
referred to as Compound (M-16)) with the compound (R-12),
followed by reacting the reaction mixtures with ammonia.
35 R2 R CH 3 R2 37 N(O)S R 0 3 (O)nS
38 R O\ (R-7)CI- NH3 R NR35
(R6)p (Rg (M-16) (M-17)
10 [wherein R38 represents a halogen atom, or a Cl-C4 alkoxy
group, and the symbols are the same as defined above.]
The reaction may be carried out by using the compound
(M-16) instead of the compound (M-7) according to the
similar method to that described in Process 5.
15 [0065]
Reference Process 5
The compound (M-16) may be prepared by reacting a
compound represented by formula (m-15) (hereinafter,
referred to as Compound (M-15)) with a compound represented
20 by formula (R-16) (hereinafter, referred to as Compound (R
16)) in the presence of a base. 87
R 2 ,R2 (0)S/. (O)"S
N ORY CH 3 N 38 R \ (R-16) R38 /
R (R% (M-15) (M-16)
[wherein RY represents a methyl group, or an ethyl group,
and the other symbols are the same as defined above.]
The compound (M-15) is a commercially available
5 compound, or may be prepared according to the similar
method to that described in International Publication No.
2014/204730.
The compound (R-16) is a commercially available
compound, or may be prepared according to the method
10 described in Journal of Molecular Catalysis A: Chemical,
2011, 341 (1-2), 57-62.
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
alcohols, ethers, aromatic hydrocarbons, polar aprotic
15 solvents, and mixed solvents thereof.
Examples of the base to be used in the reaction
include n-butyl lithium, s-butyl lithium, t-butyl lithium,
lithium diisopropylamide, sodium bis(trimethylsilyl)amide,
potassium bis(trimethylsilyl)amide, potassium t-butoxide,
20 sodium methoxide, sodium ethoxide, and alkali metal
hydrides. 88
In the reaction, the compound (R-16) is usually used
within a range of 1 to 5 molar ratio(s), and the base is
usually used within a range of 1 to 5 molar ratio(s), as
opposed to 1 mole of the compound (M-15). Preferably, the
5 compound (R-16) is usually used within a range of 1 to 1.1
molar ratio(s), and the base is usually used within a range
of 1 to 2 molar ratio(s), as opposed to 1 mole of the
compound (M-15).
The reaction temperature is usually within a range of
10 -78 to 100°C. The reaction period of the reaction is
usually within a range of 0.5 to 12 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
15 worked up (for example, drying and concentration) to give
the compound (M-16).
The compound (M-15) and the compound (M-16) are
commercially available compounds or may be prepared by
known methods.
20 [0066]
Reference Process 6
A compound represented by formula (M-4a) (hereinafter,
referred to as Compound (M-4a)) and a compound represented
by formula (M-4b) (hereinafter, referred to as Compound (M
25 4b) may be prepared according to a method described below. 89
R2 R2 (O)oS (O)'S
4 (3 H-O N (R3' V
(R (R (M-3) (M-4a)
/R2 (O)nS
3 V5 (R )q
(Re)p (M-4b)
[wherein, V 4 represents a chlorine atom or a bromine atom,
V 5 represents a fluorine atom or an iodine atom, and the
other symbols are the same as defined above]
5 First, a method for preparing the compound (M-4a) from
the compound (M-3) is described.
The compound (M-la) may be prepared by reacting the
compound (M-3) with phosphoryl chloride or phosphoryl
bromide.
10 The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
aromatic hydrocarbons.
When phosphoryl chloride is used, phosphoryl chloride
may be used also as a solvent.
15 In the reaction, phosphoryl chloride or phosphoryl 90
bromide is usually used within a range of 1 to 10 molar
ratio(s) as opposed to 1 mole of the compound (M-3).
The reaction temperature is usually within a range of
0 to 150°C. The reaction period of the reaction is usually
5 within a range of 0.5 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
worked up (for example, drying and concentration) to give
10 the compound (M-4a).
[0067]
Next, a method for preparing the compound (M-4b) from
the compound (M-4a) is described.
The compound (4-b) may be prepared by reacting the
15 compound (M-4a) with a inorganic fluoride compound or an
inorganic iodide compound.
The reaction is usually carried out in a solvent.
Examples of the solvents to be used in the reaction include
nitriles, polar aprotic solvent, nitrogen-containing
20 aromatic compounds, and mixed solvents thereof.
Examples of the inorganic fluoride compound to be used
in the reaction include potassium fluoride, sodium fluoride
and cesium fluoride.
Examples of the inorganic iodide compound to be used
25 in the reaction include potassium iodide and sodium iodide. 91
When the compound (M-4b) wherein V5 represents a
fluorine atom is prepared, the inorganic fluoride compound
is usually used within a range of 1 to 10 molar ratio(s) as
opposed to 1 mole of the compound (M-4a).
5 When the compound (M-4b) wherein V5 represents an
iodine atom is prepared, the inorganic iodide compound is
usually within a range of 1 to 10 molar ratio(s) as opposed
to 1 mole of the compound (M-4a).
The reaction temperature is usually within a range of
10 0 to 2500C. The reaction period of the reaction is usually
within a range of 0.5 to 24 hours.
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
15 worked up (for example, drying and concentration) to give
the compound (M-4b).
[0068]
Reference Process 7
A compound represented by formula (M-19) (hereinafter,
20 referred to as Compound (M-19)) may be prepared according
to a method described below. 92
R2 34 (O)nS R
RS N8 R35 NR35 HN 3 6 R R /4 R /R (O)nS' (R (O)'S R 34 N (R5(M-18a) N 38 R38 N (R-5) + R2 R R5 N~ NH 2 /N * N (O)nS R34 N R3 (R>)p N 3 (R), (M-14) R384/ (M-19) Na HN R36
(R 6)p ORv (M-18b)
(wherein the symbols are the same as defined above.]
The reaction may be prepared by using a compound
represented by formula (M-14) (hereinafter, referred to as
5 Compound (M-14)) instead of the compound (M-20) according
to the similar method to that described in Process 8.
[0069]
Reference Process 8
The compound (M-19) may be prepared according to a
10 method described below. 93
R 35 R 2 R34/j R36 R 2 (O) S (O)nS R 34 (R-5)y N N 0 R38 / R3 / Nt 0 N:\ 0 R3 R36
(R6)p (R 6) (M-16) (M-25)
R2R2 R2 (O)nS R 34 (0)nS R 34 (O)'S R34
R /N RS + R3 / R 8 R/N Nt- HN N> HN R3 6 N
(R) R (R6)p OR(R (M-18a) (M-18b) (M-19) [wherein the symbols are the same as defined above.]
The reaction may be prepared by using a compound
represented by formula (M-16) (hereinafter, referred to as
5 Compound (M-16)) instead of the compound (M-7) according to
the similar method to that described in Process 11.
[0070]
Reference Process 9
A compound represented by formula (M-28) (hereinafter,
10 referred to as Compound (M-28)) may be prepared by reacting
a compound represented by formula (M-16) (hereinafter,
referred to as Compound (M-16)) with the compound (R-12),
followed by reacting the reaction mixtures with ammonia. 94
R 3 5 CH 3 ,R2 R360 R2 (O)nS CCH 3 (O)nS N /N (R-12) NH 3 5 R 3 R3 8 R3 /E Na 0 Nm- N
(R6)p (R6 (M-16) (M-28)
[wherein the symbols are the same as defined above.]
The reaction may be prepared by using the compound (M
16) instead of the compound (M-7) according to the similar
5 method to that described in Process 5.
[0071]
Reference Process 10
A compound represented by formula (M-29) (hereinafter,
referred to as Compound (M-29)) may be prepared by reacting
10 the compound (M-14) with the compound (R-8).
)2~R352 R2 R370 / R3/R (O)nS (O)nS
0 NR3 R38 N (R-8) R38 N2 N N NH2N- NH2 - \ z 6\ R36 (Ra)p (Ry (M-14) (M-29)
[wherein the symbols are the same as defined above.]
The reaction may be prepared by using the compound (M
14) instead of the compound (M-20) according to the similar
15 method to that described in Process 10.
[0072]
Reference Process 11 95
The compound (M-31) may be prepared by reacting the
compound (M-30) with ammonia.
R2 R2 (O)"S (O)"S
40 40 R R / " 0 N N NH 2 (RS~ (Ra (M-30) (M-31)
[wherein the symbols are the same as defined above.]
5 The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include
ethers, aromatic hydrocarbons, nitriles, alcohols, polar
aprotic solvents, water, and mixed solvents thereof.
The ammonia to be used in the reaction may be in the
10 form of a gas, or may be in the form of an aqueous solution
or an alcoholic solution. Alternatively, ammonium
carboxylate such as ammonium acetate; ammonium phosphate
such as ammonium dihydrogenphosphate; ammonium carbonate;
ammonium halides such as ammonium chloride may be used.
15 In the reaction, the ammonia is usually used within a
range of 0.1 to 100 molar ratio(s) as opposed to 1 mole of
the compound (M-30).
The reaction temperature is usually within a range of
0 to 200°C. The reaction period of the reaction is usually
20 within a range of 0.5 to 24 hours.
When the reaction is completed, to the reaction 96
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
worked up (for example, drying and concentration) to give
the compound (M-31).
5 [0073]
Reference Process 12
The compound (M-2) may be prepared by reacting the
compound (M-1) with a sulfating agent.
V HS
3 N (R3) R1-O (R ) ' Ri-O N- A'NZ\ A/ (R6)p (R (M-1) (M-2)
10 [wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent.
Examples of the solvents to be used in the reaction include
ethers, aromatic hydrocarbons, nitriles, polar aprotic
solvent, and mixed solvents thereof.
15 Examples of the sulfating agent to be used in the
reaction include sodium sulfide and sodium hydrogen sulfide.
In the reaction, the sulfating agent is usually used
within a range of 1 to 10 molar ratio(s) as opposed to 1
mole of the compound (M-1).
20 The reaction temperature is usually within a range of
-20 to 150°C. The reaction period of the reaction is
usually within a range of 0.5 to 24 hours. 97
When the reaction is completed, to the reaction
mixtures is added water, and the reaction mixtures are then
extracted with organic solvents, and the organic layers are
worked up (for exmaple, drying and concentration) to give
5 the compound (M-2).
In the reaction, V is preferably a fluorine atom or a
chlorine atom.
[0074]
Examples of the compound (M-l) include the following
10 compounds.
[0075]
The compound (M-l) wherein R' represents a C2-Cl0
haloalkyl group, or a (Cl-C5 alkoxy)C2-CS alkyl group
having one or more halogen atoms; and R3 represents
15 independently of each other a Cl-C6 chain hydrocarbon group
optionally having one or more substituents selected from
Group B, a phenyl group optionally having one or more
substituents selected from Group D, a 5 or 6 membered
aromatic heterocyclic group optionally having one or more
20 substituents selected from Group D, a OR, a NR"R, a
NR2 NR"R 2 , or a halogen atom.
The compound (M-1) wherein R' represents a C2-ClO
haloalkyl group, or a (Cl-C5 alkoxy)C2-C5 alkyl group
having one or more halogen atoms; and R3 represents
25 independently of each other a Cl-C6 chain hydrocarbon group 98
optionally having one or more substituents selected from
Group B, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
heterocyclic group having one to two nitrogen atoms (the 6
5 membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group having one to four
nitrogen atoms (the 5 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
10 Group D) , a OR12 , a NR R, a NR2 NRR2, or a halogen atom.
The compound (M-1) wherein A' represents a nitrogen
atom or a CH; V2 represents a fluorine atom, or a chlorine
atom; R' represents a C2-C10 haloalkyl group, or a (Cl-C5
alkoxy)C2-C5 alkyl group having one or more halogen atoms;
15 R 3 represents independently of each other a C1-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, or a halogen atom; and R6 represents independently
of each other a Cl-C6 alkyl group optionally having one or
halogen atoms, or a halogen atom.
20 The compound (M-1) wherein A' represents a nitrogen
atom or a CH; V2 represents a fluorine atom, or a chlorine
atom; R' represents a C2-C10 haloalkyl group having two or
more fluorine atoms; R3 represents independently of each
other a Cl-C6 chain hydrocarbon group optionally having one
25 or more halogen atoms, or a halogen atom; and p represents 99
0.
The compound (M-1) wherein A' represents a nitrogen
atom or a CH; V2 represents a fluorine atom, or a chlorine
atom; R' represents a C2-C10 haloalkyl group having two or
5 more fluorine atoms; R3 represents independently of each
other a Cl-C6 chain hydrocarbon group optionally having one
or more halogen atoms, or a halogen atom; and p represents
0.
The compound (M-1) wherein I represents a nitrogen
10 atom or a CH; V2 represents a fluorine atom, or a chlorine
atom; R represents a 2,2,2-trifluoroethyl group, a
2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3
pentafluoropropyl group, a 1,1,2, 3 ,3,3-hexafluoropropyl
group, a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group,
15 or a 2,2,3,4,4,4-hexafluorobutyl group; q represents 0 or
1; R3 represents a trifluoromethyl group; and p represents
0.
10076)
Examples of the compound (M-2) include the following
20 compounds.
[0077]
The compound (M-2) wherein R1 represents a C2-C10
haloalkyl group, or a (Cl-C5 alkoxy)C2-C5 alkyl group
having one or more halogen atom; and R3 represents
25 independently of each other a Cl-C6 chain hydrocarbon group 100
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
Group D, a 5 or 6 membered aromatic heterocyclic group
optionally having one or more substituents selected from
5 Group D, a OR", a NR'R", a NR2NR'R , or a halogen atom.
The compound (M-2) wherein R' represents a C2-C10
haloalkyl group, or a (Cl-CS alkoxy)C2-C5 alkyl group
having one or more halogen atom; and R3 represents
independently of each other a Cl-C6 chain hydrocarbon group
10 optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
Group D, a 6 membered aromatic heterocyclic group having
one to two nitrogen atoms (the 6 membered aromatic
heterocyclic group may optionally have one or more
15 substituents selected from Group D), a 5 membered aromatic
heterocyclic group having one to four nitrogen atoms (the 5
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D)., a OR!2 , a
NR"12, a NR 9NR"R"2, or a halogen atom.
20 The compound (M-2) wherein A' represents a nitrogen
atom or a CH; R1 represents a C2-ClO halcalkyl group or a
(Cl-C5 alkoxy)C2-C5 alkyl group having one or more halogen
atom; R3 represents independently of each other a Cl-C6
chain hydrocarbon group optionally having one or more
25 halogen atoms, or a halogen atom; and R6 represents 101
independently of each other a C1-C6 alkyl group optionally
having one or halogen atoms or a halogen atom.
The compound (M-2) wherein A' represents a nitrogen
atom or a CH; RI represents a C2-C10 alkyl group having two
5 or more fluorine atoms; R3 represents independently of each
other a Cl-C6 chain hydrocarbon group optionally having one
or more halogen atoms, or a halogen atom; and p represents
0.
The compound (M-2) wherein A' represents a nitrogen
10 atom or a CH; R' represents a C2-C10 alkyl group; q
represents 0; and p represents 0.
The compound (M-2) wherein A' represents a nitrogen
atom or a CH; R represents a C2-C10 haloalkyl group having
two or more fluorine atoms; R3 represents independently of
15 each other a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, or a halogen atom; and p
represents 0.
The compound (M-2) wherein A' represents a nitrogen
atom or a CH; R represents a 2,2,2-trifluoroethyl group, a
20 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3
pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl
group, a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group,
or a 2,2,3,4,4,4-hexafluorobutyl group; q represents 0 or
1; R 3 represents a trifluoromethyl group; and p represents
25 0. 102
[0078]
Examples of the compound (M-3) include the following
compounds.
[0079]
5 The compound (M-3) wherein R2 represents a C1-C6 alkyl
group optionally having one or halogen atoms; and R
represents independently of each other a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
10 substituents selected from Group D, a 5 or 6 membered
aromatic heterocyclic group optionally having one or more 2 substituents selected from Group D, a OR, a NR"PR , a
NR2 NRR, or a halogen atom.
The compound (M-3) wherein R 2 represents a Cl-C6 alkyl
15 group optionally having one or halogen atoms; and R3
represents independently of each other a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
20 heterocyclic group having one to two nitrogen atoms (the 6
membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group having one to four
nitrogen atoms (the 5 membered aromatic heterocyclic group
25 may optionally have one or more substituents selected from 103
Group D), a OR2, a NR1lR12, or a halogen atom.
The compound (M-3) wherein A' represents a nitrogen
atom, or a CH; R2 represents an ethyl group; q represents 0,
1, 2, or 3; R3 represents independently of each other a Cl
5 C6 chain hydrocarbon group optionally having one or more
halogen atoms, a 5 or 6 membered aromatic heterocyclic
group optionally having one or more substituents selected
1 1121 2 i 1 2 from Group D, a OR, a NR"R , a NRNR R, or a halogen
atom; and R6 represents independently of each other a Cl-C6
10 alkyl group optionally having one or halogen atoms, or a
halogen atom.
The compound (M-3) wherein A' represents a nitrogen
atom, or a CH; R2 represents an ethyl group; q represents 0,
1, 2, or 3; R5 represents independently of each other a Cl
15 C6 chain hydrocarbon group optionally having one or more
halogen atoms, or a halogen atom; p represents 0, 1, 2, or
3; and R represents independently of each other a Cl-C6
alkyl group optionally having one or halogen atoms or a
halogen atom.
20 [0080]
Examples of the compound (M-4) include the following
compounds.
[0081]
The compound (M-4) wherein R2 represents a Cl-C6 alkyl
25 group optionally having one or halogen atoms; and R3 104
represents independently of each other a C1-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 5 or 6 membered
5 aromatic heterocyclic group optionally having one or more
substituents selected from Group D, a OR, a NR R, a
NR9NRIR, or a halogen atom.
The compound (M-4) wherein R2 represents a Cl-C6 alkyl
group optionally having one or halogen atoms; and R3
10 represents independently of each other a C1-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a phenyl group optionally having one or more
substituents selected from Group D, a 6 membered aromatic
heterocyclic group having one to two nitrogen atoms (the 6
15 membered aromatic heterocyclic group may optionally have
one or more substituents selected from Group D), a 5
membered aromatic heterocyclic group having one to four
nitrogen atoms (the 5 membered aromatic heterocyclic group
may optionally have one or more substituents selected from
20 Group D), a OR , a NR1 R2, or a halogen atom.
The compound (M-4) wherein Al represents a nitrogen
atom, or a CH; V represents a fluorine atom, a chlorine
atom, or an iodine atom; R 2 represents an ethyl group; R3
represents independently of each other a Cl-C6 chain
25 hydrocarbon group optionally having one or more halogen 105
atoms, or a halogen atom; and RE represents independently
of each other a Cl-C6 alkyl group optionally having one or
halogen atoms, or a halogen atom.
[0082]
5 Examples of the compound (M-30) include the following
compounds.
0083)
The compound (M-30) wherein R' represents a C2-C10
haloalkyl group, or a (Cl-C5 alkoxy)C2-C5 alkyl group
10 having one or more halogen atom; and R2 represents a Cl-C6
alkyl group optionally having one or halogen atoms.
The compound (M-30) wherein R40 represents a halogen
atom, or a OR'; R represents a C2-C10 haloalkyl group, or
a (Cl-CS alkoxy)C2-C5 alkyl group having one or more
15 halogen atom; and R 2 represents a Cl-C6 alkyl group
optionally having one or halogen atoms.
The compound (M-30) wherein R40 represents a halogen
atom, or a OR1 ; R represents a C2-C10 haloalkyl group; and
R 2 represents an ethyl group.
20 The compound (M-30) wherein R40 represents a halogen
atom, or a OR; R' represents a C2-C10 haloalkyl group; R 2
represents an ethyl group; and p represents 0.
The compound (M-30) wherein R40 represents a halogen
atom; and R2 represents a Cl-C6 alkyl group optionally
25 having one or halogen atoms. 106
The compound (M-30) wherein R40 represents a fluorine
atom or a chlorine atom; and R2 represents an ethyl group;
n represents 2; and p represents 0.
The compound (M-23) wherein R4° represents a OR; R'
5 represents a C2-C10 haloalkyl group or a (Cl-CS alkoxy)C2
C5 alkyl group having one or more halogen atom; and R2
represents an ethyl group.
The compound (M-23) wherein R 4 ° represents a OR'; RI
represents a C2-C1O haloalkyl group having two or more
10 fluorine atoms or a (Cl-CS alkoxy)C2-C5 alkyl group having
one or more halogen atom; R2 represents an ethyl group; n
represents 2; and p represents 0.
1 The compound (M-30) wherein R 40 represents a OR ; R'
represents a 2,2,2-trifluoroethyl group, a 2,2,3,3
15 tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl
group, a 1,1,2,3,3,3-hexafluoropropyl group, a 1,1,2
trifluoro-2-(trifluoromethoxy)ethyl group, or a
2,2,3,4,4,4-hexafluorobutyl group; R2 represents an ethyl
group; n represents 2; and p represents 0.
20 The compound (M-30) wherein R 4a represents a Cl-C4
alkoxy group; R2 represents an ethyl group; p represents 0,
1, 2, or 3; and RE represents independently of each other a
Cl-C6 alkyl group optionally having one or halogen atoms, a
NR'R", a C (O) ORE, a OC (O) OR, a cyano group, a nitro
25 group, or a halogen atom. 107
The compound (M-30) wherein R 40 represents a Cl-C3
alkoxy group; R- represents an ethyl group; n represents 2;
and p represents 0.
[0084]
5 Examples of the compound (M-31) include the following
compounds.
[0085]
The compound (M-31) wherein R1 represents a C2-C10
haloalkyl group, or a (Cl-CS alkoxy)C2-C5 alkyl group
10 having one or more halogen atom; and R2 represents a Cl-C6
alkyl group optionally having one or halogen atoms.
The compound (M-31) wherein R 4 0 represents a halogen
atom; and R2 represents a Cl-C6 alkyl group optionally
having one or halogen atoms;
15 The compound (M-31) wherein R4° represents a fluorine
atom or a chlorine atom; R2 represents an ethyl group; n
represents 2; and p represents 0.
The compound (M-31) wherein R 4 D represents a OR ; Ri
represents a C2-C10 haloalkyl group, or a (Cl-CS alkoxy)C2
20 CS alkyl group having one or more halogen atom; and R2
represents an ethyl group.
The compound (M-31) wherein R40 represents a OR; R1
represents a C2-C10 haloalkyl group having two or more
fluorine atoms, or a (Cl-CS alkoxy)C2-C5 alkyl group having
25 one or more halogen atom; R represents an ethyl group; n 108
represents 2; and p represents 0.
The compound (M-31) wherein R40 represents a OR1 ; R
represents a 2,2,2-trifluoroethyl group, a 2,2,3,3
tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl
5 group, a 1,1,2,3,3,3-hexafluoropropyl group, a 1,1,2
trifluoro-2-(trifluoromethoxy)ethyl group, or a
2,2,3,4,4,4-hexafluorobutyl group; R2 represents an ethyl
group; n represents 2; and p represents 0.
The compound (M-31) wherein R40 represents a Cl-C4
10 alkoxy group; and R2 represents an ethyl group.
The compound (M-31) wherein R" represents a C1-C3
alkoxy group; R2 represents an ethyl group; n represents 2;
and p represents 0.
[0086]
15 Next, specific examples of the compound of the present
invention are shown below.
[0087]
/R2 R6b (O)nS R3a N R--O \ R3b (I-C) N- N/_ Rea R3e
The compound represented by formula (I-C) of the
20 present invention wherein n represents 2; R3a, Rb, R3c, Ra,
and R61 represent a hydrogen atom; and R' and R2 represent
any combination indicated in Table 1 to Table 5 109
(hereinafter, referred to as Compound Group SX1).
Table 1
[Table 11 110
H' P,
OF2HCH2 CH3CH2
OH 3CF2 CH 3CH2
CF3 CH2 CH3CH2 cc 1 3 C H 2 CH 3CH2
CF-HCF2 CH 3CH 2
CHCIFCF2 CH 3CH2
CF3CH20H21 CH 3CH2
CF2HCF2CH2 CH 3CH2
CF3CF2CH2 CH3CH2
CBrF2,CF 2 CH 3CH2
CF3CFHCE2 CH3CH2
OH3CF2 OCH2 CH3CH2
CF3CH (CH 3 ) CH3 CH2
CF3 C (CH 3 )2 CH3CH2
CH (CHA 2 CH (CF3 ) CH3CH2
(OF3 ) 2 CH CH 3CH2
CH3CN,CH2 (CF 3 ) CH3CH2
CF3jCC12CH2 CH3CH2
CF3CF2,CH (OH3) CH3 CH2
CF3CF2 CH (OH2CH3 ) CH3CH2
O (OH3 ) (CF3 ) 2CW2 CH3CH2
CF3 CFHCF2 CH2 OH30 2
CF3 (OF2 ) 20H2 CH3CH2
CBrF 2OF 2CH2OH 2 0H30H2
CF3CFHCF2CH(OH3 ) 0H30H21
Table 2 111
[Table 2]
R, R 2
CF 3CH=CHCH 2 CH 3CH 2
CF 3 (CF 2 ) 3 CH2 CH3CH 2
CF3 (CF 2 ) 4 CH 2 CH 3CH 2
CF3 (CF 2 ) 3CH 2CH 2 CH 3 CH2
CF (CF 3 ) 2 CF 2CF2CH2CH 2 CH 3 CH 2
CF2H (CF2 ) 3CH 2 CH 3CH 2
CF 2 H (CF2 )CH 2 CH 3 CH 2
CF3 (CF 2 ) 3 CH 2 CH 2 CH 2 CH3CH 2
CF 3CF 2 (CH 2 ) 5 CH2 CH 3CH2
CF3 (CF 2 )5 CH 2 CH2 CH2 CH3CH 2
CF3 (CF 2 ) 3CH 2 (CH 2 ) 4 CH2 CH3CH2
CF3 (CF 2 )5 CH 2 CH 2 CH3 CH2
CF (CF 3 ) 2 CH 2 (CH 2 ) 4 CH 2 CH3 CH2
CF30CFHCF2 CH3 CH2
CH 30CH 2 CF2 CH 2 CH 3 CH 2
CF 3CH 2 0CH 2 CF2 CH 2 CH 3CH 2
CHFCFCH 2 CH 3CH 2
CH2ClCF 2 CH2 CH 3CH 2
CH 2 BrCF 2CH2 CH 3CH2
CH 3 OCH 2 (CF 2 ) 2 CH2 CH 3 CH2
CF 3 CH2OCH 2 (CF2) 2 CH 2 CH3 CH2
CH 2 F (CF2 ) 2 CH 2 CH3CH2
CH 2CI (CF 2 ) 2 CH 2 CH3 CH2
CH 2Br (CF2 ) 2 CH2 CH3 CH2
CH 30CH 2 (CF 2 )3CH 2 CH 3 CH 2 112
Table 3
[Table 3]
RI R2
CH CF3CH2 0CH 2 (CF 2 ) 3 CH 2 CH 3 2
CH 30CH 2 (CF2)3CH2 CH3CH2
CF3CH20CH2(CF2 )3CH2 CH3CH2
CHF (CF 2 ) 3CH2 CH3CH2
CH 2Cl(CF2)3CH2 CH3CH 2
CH2Br (CF 2 ) 3CH2 CH3CH2
CH 3 OCH 2 (CF 2 ) 4 CH 2 CH3CH2
CF3CH 2 0CH 2 (CF 2 ) 4 CH 2 CH3CH 2
CH 2 F (CF 2 ) 4 CH 2 CH3CH 2
CHCl (CF 2 ) 4CH 2 CH3CH2
CH 2Br (CF2 ) 4CH2 CH3CH 2
CF3CF2OCFHCF2 CH3CH 2
C3CF2CF20CFHCF2 CH3CH2
CF3CF2 CF20CF (CF 3 ) CH 2 CH3CH 2
CF3CHOCH2 CH2 CH3CH2
5 Table 4
[Table 4] 113
F C 3 CH3CH2 ,
FC CH3CH2 F F
F F FFF F
OH3CH2 F
F aCH 3CH2
F30 la CH3CH2
C H F30 I
Table 5
[Table 5] 114
P P2
CH3SCH2 CF2 CH 2 CH 3 CH 2
CH 3 S (0) CH 2CF 2 CH 2 CH3CH 2
CH3S (0) 2CH 2CF 2 CH 2 CH 3CH 2
CF 3CH 2 SCH 2 CF 2 CH2 CH 3CH 2
CF 3CH 2S (0) CH 2 CF2 CH 2 CH3CH2
CF 3CH 2 S (0) 2CH 2 CF2CH 2 CH 3CH 2
CF 3 SCH 2 CF 2CH2 CH 3CH2
CF 3S (0) CH2CF2CH2 CH 3CH 2
CF3S (0) 2 CH2 CF2 CH 2 CH3CH 2
CF3 SCH 2 (CF 2 ) 2 CH2 CH3CH 2
CF3 S (0) CH2 (CF 2 )2 CH2 CH 3CH 2
CF3 S (0) 2 CH2 ( CF 2 ) 2 CH 2 CH2 CH2
CF3SCH 2 (CF 2 ) 3 CH2 CH 3 CH 2
CF 3S(0)CH2 (CF2 ) 3CH 2 CH3CH 2
CF 3 S(0) 2 CH2 (CF 2 ) 3 CH 2 CH 3CH 2
CF 3SCH 2 (CF2 ) 4 CH CH 3CH 2
CF3S (0) CH 2 (CF 2 ) 4CH2 CH 3CH 2
CF3S (0) 2 CH 2 (CF2 ) 4 CH2 CH 3CH 2
CF 3CH 2 SCH 2CH2 CH 3CH 2
CF 3 CH 2 S (0) CH2 CH 2 CH3CH2
CF 3CH 2 S (0) 2CH 2 CH 2 CH3CH 2
CE3SCH 2 CH2 CH 3CH 2
CF3 S (0)CH2 CH2 CH2 CH 2
CF3 S(0) 2 CH2 CH2 CH 3 CH 2
£0088]
The compound represented by formula (I-C) of the
present invention wherein n represents 1; Ra, R,, R3, R 6a
and Ra represent a hydrogen atom; and R' and R 2 represent 115
any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX2).
The compound represented by formula (I-C) of the
6a present invention wherein n represents 0; Raa, RS b, R3, R ,
5 and JRC represent a hydrogen atom; and Ra and R2 represent
any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX3).
The compound represented by formula (I-C) of the
6 present invention wherein n represents 2; RS , RSC, R a, and
10 R6b represent a hydrogen atom; R3b represents a
trifluoromethyl group; and R and R2 represent any
combination indicated in Table 1 to Table 5 (hereinafter,
referred to as Compound Group SX4).
The compound represented by formula (I-C) of the
15 present invention wherein n represents 1; Ra, R3:, RE, and
R 6 represent a hydrogen atom; R represents a
trifluoromethyl group; and R' and R2 represent any
combination indicated in Table 1 to Table 5 (hereinafter,
referred to as Compound Group SX5).
20 The compound represented by formula (I-C) of the
present invention wherein n represents 0; R 5a, R3,, R6a, and
R6b represent a hydrogen atom; R represents a
trifluoromethyl group; and R' and R2 represent any
combination indicated in Table 1 to Table 5 (hereinafter,
25 referred to as Compound Group SX6). 116
[0089]
R2 Reb (O)nS R3a N R'-O N R 3b (I-D)
4 3 R6 a R R e
The compound represented by formula (I-D) of the
present invention wherein R 4 represents a hydrogen atom; n
5 represents 2; R a, , R3 , R ", and Rub represent a hydrogen
atom; and R1 and R 2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
Group SX7).
The compound represented by formula (I-D) of the
10 present invention wherein R 4 represents a hydrogen atom; n
represents 1; R3, RD, R3 , Ra, and REb represent a hydrogen
atom; and R1 and R 2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
Group SX8).
15 The compound represented by formula (I-D) of the
present invention wherein R 4 represents a hydrogen atom; n
represents 0; R3a, 3b, R3°, R6a, and Ru6 represent a hydrogen
atom; and Ri and R2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
20 Group SX9).
The compound represented by formula (I-D) of the
present invention wherein R4 represents a hydrogen atom; n 117
represents 2; R", R3 , R60, and R>b represent a hydrogen
atom; R L represents a trifluoromethyl group; and R1 and R'
represent any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX10).
5 The compound represented by formula (I-D) of the
present invention wherein R4 represents a hydrogen atom; n
represents 1; R3a, RBC, R, and RO represent a hydrogen
atom; R2L represents a trifluoromethyl group; and R1 and R
represent any combination indicated in Table 1 to Table 5
10 (hereinafter, referred to as Compound Group SX11).
The compound represented by formula (I-D) of the
present invention wherein R4 represents a hydrogen atom; n
represents 0; R, RS, R3, and REb represent a hydrogen
atom; REb represents a trifluoromethyl group; and R3 and R 2
15 represent any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX12).
[0090]
The compound represented by formula (I-D) of the
present invention wherein R4 represents a fluorine atom; n
20 represents 2; R3', R3b, RS, R0a, and REb represent a hydrogen
atom; and R1 and R2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
Group SX13).
The compound represented by formula (I-D) of the
25 present invention wherein R4 represents a fluorine atom; n 118
3 3 6 represents 1; R 3a, R b, R C, R a, and REb represent a hydrogen
atom; and R' and R2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
Group SX14).
5 The compound represented by formula (I-D) of the
present invention wherein R4 represents a fluorine atom; n
represents 0; Raa, R3b, R3C, R 6 a, and Rcb represent a hydrogen
atom; and R' and R2 represent any combination indicated in
Table 1 to Table 5 (hereinafter, referred to as Compound
10 Group SX15).
The compound represented by formula (I-D) of the
present invention wherein R 4 represents a fluorine atom; n
6 represents 0; Ria, R' , R a, and REO represent a hydrogen
atom; R3b represents a trifluoromethyl group; and R' and R2
15 represent any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX16).
The compound represented by formula (I-D) of the
present invention wherein R 4 represents a fluorine atom; n
represents 1; R3a, R3 , REa, and RE represent a hydrogen
20 atom; R 3b represents a trifluoromethyl group; and R' and R2
represent any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX17).
The compound represented by formula (I-D) of the
present invention wherein R4 represents a fluorine atom; n
25 represents 0; R, R°, Ra, and RE represent a hydrogen 119
atom; R3 represents a trifluoromethyl group; and R and R2
represent any combination indicated in Table 1 to Table 5
(hereinafter, referred to as Compound Group SX18).
[0091]
5 The compound of the present invention may be mixed or
combined with one or more kinds of ingredients selected
from a group consisting of the following Group (a), Group
(b), Group (c), and Group (d) (hereinafter, referred to as
Present active ingredient). Preferably, the present active
10 ingredient includes one or more kinds of ingredients
selected from a group consisting of sub group a-1, sub
group a-2, sub group a-3, sub group a-4, sub group a-5, sub
group a-6, sub group a-7, sub group a-8, sub group a-9, sub
group b-1, sub group b-2, sub group b-3, sub group b-4, sub
15 group b-5, sub group b-6, sub group b-7, sub group b-8, sub
group b-9, sub group b-10, sub group b-11, sub group b-12,
subgroup b-13, sub group b-14, sub group b-15, sub group
b-16, sub group c-1, sub group c-2, and Group (d).
Particularly preferably, the present active ingredient
20 includes one or more kinds of ingredients selected from a
group consisting of sub group a-6, sub group a-9, sub group
b-1, sub group b-3, sub group b-4, sub group b-5, sub group
b-9, sub group b-ll, and sub group b-13.
[0092]
25 Group (a) represents a group of one or more kinds of 120
insecticidal ingredients, miticidal ingredients, and
nematicidal ingredients selected from the group consisting
of the following sub group a-I to a-10. The numerical
number in bracket represents a CAS register number.
5
Sub group a-i:
Carbamate acetylcholinesterase (AChE) inhibitor group
selected from the group consisting of alanycarb, aldicarb,
bendiocarb, benfuracarb, butocarboxim, butoxycarboxim,
10 carbaryl: NAC, carbofuran, carbosulfan, ethiofencarb,
fenobucarb: BPMC, formetanate, furathiocarb, isoprocarb:
MIPC, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,
propoxur: PHC, thiodicarb, thiofanox, triazamate,
trimethacarb, XMC, and xylylcarb.
15 [0093]
Sub group a-2:
Organophosphorus acetylcholinesterase (AChE) inhibitor
group selected from the group consisting of acephate,
azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,
20 chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos,
chlorpyrifos-methyl, coumaphos, cyanophos: CYAP, demeton-S
methyl, diazinon, dichlorvos: DDVP, dicrotophos, dimethoate,
dimethylvinphos, disulfoton, EPN, ethion, ethoprophos,
famphur, fenamiphos, fenitrothion: MEP, fenthion: MPP,
25 fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl- 121
0-(methoxyaminothiophosphoryl)salicylate, isoxathion,
malathion, mecarbam, methamidophos, methidathion: DMTP,
mevinphos, monocrotophos, naled: BRP, omethoate,
oxydemeton-methyl, parathion, parathion-methyl, phenthoate:
5 PAP, phorate, phosalone, phosmet: PMP, phosphamidon, phoxim,
pirimiphos-methyl, profenofos, propetamphos, prothiofos,
pyraclofos, pyridaphenthion, quinalphos, sulfotep,
tebupirimfos, temephos, terbufos, tetrachlorvinphos,
thiometon, triazophos, trichlorfon: DEP, and vamidothion.
10 [0094)
Sub group a-3:
GABA-gated chloride channel blockers group selected from
the group consisting of ethiprole, fipronil, flufiprole,
chlordane, endosulfan, and alpha-endosulfan.
15 [0095)
Sub group a-4:
GABA-gated chloride channel allosteric modulator group
selected from the group consisting of afoxolaner,
fluralaner, broflanilide, and fluxametamide.
20 [0096]
Sub group a-5:
Sodium channel modulator group selected from the group
consisting of acrinathrin, allethrin, bifenthrin, kappa
bifenthrin, bioallethrin, bioresmethrin, cycloprothrin,
25 cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, 122
lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta
cypermethrin, theta-cypermethrin, zeta-cypermethrin,
cyphenothrin, deltamethrin, empenthrin, esfenvalerate,
etofenprox, fenpropathrin, fenvalerate, flucythrinate,
5 flumethrin, fluvalinate, tau-fluvalinate, halfenprox,
heptafluthrin, imiprothrin, kadethrin, meperfluthrin,
momfluorothrin, permethrin, phenothrin, prallethrin,
pyrethrins, resmethrin, silafluofen, tefluthrin, kappa
tefluthrin, tetramethrin, tetramethylfluthrin, tralomethrin,
10 transfluthrin, benfluthrin, flufenoprox, flumethrin, sigma
cypermethrin, furamethrin, metofluthrin, profluthrin,
dimefluthrin, epsilon-metofluthrin, epsilon-momfluorothrin,
and methoxychlor.
[0097]
15 Sub group a-6:
Nicotinic acetylcholine receptor (nAChR) competitive
modulator group selected from the group consisting of
acetamiprid, clothianidin, dinotefuran, imidacloprid,
nitenpyram, thiacloprid, thiamethoxam, sulfoxaflor,
20 flupyradifurone, triflumezopyrim, dicloromezotiaz,
cycloxaprid, and a compound represented by the following
formula: 123
N FF N FF
N CI
(1363400-41-2, hereinafter, referred to as insecticidal
compound al).
[0098]
5 Sub group a-7:
Ryanodine receptor modulator group selected from the group
consisting of chlorantraniliprole, cyantraniliprole,
cycloniliprole, flubendiamide, tetraniliprole,
cyhalodiamide, and a compound represented by the following
10 formula:
C1
H | N - I O HN 0 N- CI N
Br CI
(1104384-14-6, hereinafter, referred to as insecticidal
compound c2)
[0099]
15 Sub group a-8:
Microbial material group selected from the group consisting
of Beauveria bassiana, Beauveria bassiana strain GHA, 124
Beauveria brongniartii, Paecilomyces fumosoroseus,
Paecilomyces lilacinus, Paecilomyces tenuipes, Verticillium
lecani, Arthrobotrys dactyloides, Bacillus thuringiensis,
Bacillus firmus, Bacillus firmus strain CNCM I-1582,
5 Bacillus megaterium, Hirsutella rhossiliensis, Hirsutella
minnesotensis, Monacrosporium phymatopagus, Pasteuria
nishizawae, Pasteuria penetrans, Pasteuria usgae, and
Verticillium chlamydosporium.
[0100]
10 Sub group a-9:
Nematicidal ingredients group selected from the group
consisting of abamectin, fluazaindolizine, fluensulfone,
fluopyram, and tioxazafen.
[0101]
15 Sub group a-10:
The other group as insecticides and miticides selected from
the group consisting of spinetoram, spinosad, emamectin
benzoate, lepimectin, milbemectin, hydroprene, kinoprene,
methoprene, fenoxycarb, pyriproxyfen, methyl bromide,
20 chloropicrin, sulfuryl fluoride, sodium aluminium fluoride
or chiolite, borax, boric acid, disodium octaborate, sodium
borate, sodium metaborate, tartar emetic, dazomet, metam,
pymetrozine, pyrifluquinazone, clofentezine, hexythiazox,
diflovidazin, etoxazole, diafenthiuron, azocyclotin,
25 cyhexatin, fenbutatin oxide, propargite, tetradifon, 125
chiorfenapyr, DNOC, sulfluramid, bensultap, cartap, cartap
hydrochloride, thiocyclam, thiosultap-disodium, thiosultap
monosodium, bistrifluron, chlorfluazuron, diflubenzuron,
fluazuron, flucycloxuron, flufenoxuron, hexaflumuron,
5 lufenuron, novaluron, noviflumuron, teflubenzuron,
triflumuron, buprofezin, cyromazine, chromafenozide,
halofenozide, methoxyfenozide, tebufenozide, amitraz,
hydramethylnon, acequinocyl, fluacrypyrim, bifenazate,
fenazaquin, fenpyroximate, pyridaben, pyrimidifen,
10 tebufenpyrad, tolfenpyrad, rotenone, indoxacarb,
metaflumizone, spirodiclofen, spiromesifen, spirotetramat,
aluminium phosphide, calcium phosphide, phosphine, zinc
phosphide, calcium cyanide, potassium cyanide, sodium
cyanide, cyenopyrafen, cyflumetofen, pyflubumide,
15 flonicamid, azadirachtin, benzoximate, bromopropylate,
chinomethionat, dicofol, pyridalyl, lime sulfur, sulfur,
machine oil, nicotine, nicotine-sulfate, afidopyropen,
flometoquin, metoxadiazone, pyriminostrobin,
a compound represented by the following formula:
CI N- 0 O FF N N SF
SH3C 20 N
(1477919-27-9, hereinafter, referred to as fungicide
compound a3), 126
a compound represented by the following formula:
CI N- F F N / N SF 0 H N 3C
(1477923-37-7, hereinafter, referred to as fungicide
compound a4), and
5 a compound represented by the following formula:
N O CF 3
N 0
0
(1449021-97-9, hereinafter, referred to as fungicide
compound a5).
[0102]
10 Group (b) represents a fungicidal ingredient group
selected from the group consisting of the following sub
group b-1 to sub group b-18.
Sub group b-1
PA fungicide (Phenyl amide) selected from the group
15 consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl,
metalaxyl-M, oxadixyl, and ofurace.
[0103]
Sub group b-2
MBC fungicide (methyl benzimidazole carbamate) group
/ n n 1 /I 1 1 \ .nI I 127
selected from the group consisting of benomyl, carbendazim,
fuberidazole, thiabendazole, thiophanate, and thiophanate
methyl.
[0104]
5 Sub group b-3
Thiazole carboxamide group selected from the group
consisting of ethaboxam.
[0105]
Sub group b-4
10 SDHI (Succinate dehydrogenase inhibitor) group selected
from the group consisting of benodanil, flutolanil,
mepronil, isofetamid, fenfuram, carboxin, oxycarboxin,
thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad,
furametpyr, isopyrazam, penfiufen, penthiopyrad, sedaxane,
15 pydiflumetofen, boscalid, pyraziflumid, 3-difluoromethyl-1
methyl-N-(1,1,3-trimethylindan)-4-yl)pyrazole-4-carboxamide
(141573-94-6, hereinafter, referred to as fungicide
compound p1), 3-difluoromethyl-1-methyl-N-[(3R)-1,1,3
trimethylindan-4-yljpyrazole-4-carboxamide (1352994-67-2,
20 hereinafter, referred to as fungicide compound f2), 3
difluoromethyl-N-(7-fluoro-1,1,3-trimethylindan-4-yl)-l
methylpyrazole-4-carboxamide (1383809-87-7, hereinafter,
referred to as fungicide compound p3), 3-difluoromethyl-N
[(3R)-7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole
25 4-carboxamide (1513466-73-3, hereinafter, referred to as 128
fungicide compound P4), and N-cyclopropyl-3
(difluoromethyl)-5-fluoro-N-(5-chloro-2-isopropylbenzyl)-1
methyl-1H-pyrazole-4-carboxamide (1255734-28-1, hereinafter,
referred to as fungicide compound $5).
5 [0106]
Sub group b-5
QoI fungicide (Qo Inhibitor) group selected from the group
consisting of azoxystrobin, coumoxystrobin, enoxastrobin,
flufenoxystrobin, picoxystrobin, pyraoxystrobin,
10 mandestrobin, pyraclostrobin, pyrametostrobin,
triclopyricarb, kresoxim-methyl, trifloxystrobin,
dimoxystrobin, fenaminstrobin, metominostrobin,
orysastrobin, famoxadone, fluoxastrobin, fenamidone, and
pyribencarb.
15 [0107]
Sub group b-6
QiI fungicide (Qi Inhibitor) group selected from the group
consisting of cyazofamid, amisulbrom, binapacryl,
meptyldinocap, dinocap, and fluazinam.
20 [0108]
Sub group b-7
Thiophanate carboxamide group selected from the group
consisting of silthiofam.
[0109]
25 Sub group b-8 129
AP fungicide (Anilinopyrimidine) group selected from the
group consisting of cyprodinil, mepanipyrim, and
pyrimethanil.
[0110]
5 Sub group b-9
PP fungicide (Phenylpyrrole) group selected from the group
consisting of fenpiclonil and fludioxonil.
[0111]
Sub group b-10
10 AH fungicide (Aromaic hydrocarbons) group selected from the
group consisting of biphenyl, chloroneb, dicloran,
quintozene, tecnazene, and tolclofos-methyl.
[0112]
Sub group b-11
15 DMI fungicide (Demethylation inhibitor) group selected from
the group consisting of azaconazole, bitertanol,
bromuconazole, cyproconazole, difenoconazole, diniconazole,
diniconazole-M, fenbuconazole, fluquinconazole, flusilazole,
flutriafol, hexaconazole, imibenconazole, ipconazole,
20 ipfentrifluconazole, mefentrifluconazole, metconazole,
myclobutanil, penconazole, propiconazole, simeconazole,
tebuconazole, tetraconazole, triadimefon, triadimenol,
triticonazole, prothioconazole, triforine, pyrifenox,
pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole,
25 oxpoconazole fumarate, pefurazoate, prochloraz, and 130
triflumizole.
[0113]
Sub group b-12
CCA fungicide (Carboxylic acid amide) group selected from
5 the group consisting of dimethomorph, flumorph, pyrimorph,
benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb,
valifenalate, and mandipropamid.
[0114]
Sub group b-13
10 Piperidinyl thiazole isoxazoline group selected from the
group consisting of oxathiapiprolin.
[0115]
Sub group b-14
Tetrazolyl oxime group selected from the group consisting
15 of picarbutrazox.
[0116]
Sub group b-15
Dithiocarbamate group selected from the group consisting of
ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb,
20 and ziram.
[0117]
Sub group b-16
Phthalimide group selected from the group consisting of
captan, captafol, and folpet.
25 [0118] 131
Sub group b-17
Microbial fungicide group selected from the group
consisting of Agrobacterium radiobactor, Bacillus
amyloliquefaciens, Bacillus amyloliquefaciens strain QST713,
5 Bacillus amyloliquefaciens strain FZB24, Bacillus
amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens
strain D747, Bacillus amyloliquefaciens strain AT-332,
Bacillus pumilus, Bacillus pumilus strain GB34, Bacillus
pumilus strain QST2808, Bacillus subtilis, Erwinia
10 carotovora (CGE234M403 strain and so on), Pseudomonas
fluorescens (G7090 strain and so on), Talaromyces flavus
(SAY-Y-94-01 strain and so on), Trichoderma atroviride
(SKT-1 strain and so on), Trichoderma harzianum, and Harpin
protein.
15 [0119]
Sub group b-18
Other fungicide group selected from the group consisting of
bupirimate, dimethirimol, ethirimol, hymexazole,
octhilinone, oxolinic acid, diethofencarb, zoxamide,
20 pencycuron, fluopicolide, phenamacril, diflumetorim,
tolfenpyrad, fentin acetate, fentin chloride, fentin
hydroxide, ametoctradin, blasticidin-S, kasugamycin,
streptomycin, oxytetracycline, quinoxyfen, proquinazid,
chlozolinate, dimethachlone, iprodione, procymidone,
25 vinclozolin, edifenphos, iprobenfos, pyrazophos, 132
isoprothiolane, etridiazole, iodocarb, propamocarb,
prothiocarb, aldimorph, dodemorph, fenpropidin,
fenpropimorph, piperalin, spiroxamine, tridemorph,
fenhexamid, fenpyrazamine, pyributicarb, naftifine,
5 terbinafine, polyoxins, phthalide, pyroquilon, tricyclazole,
carpropamid, diclocymet, fenoxanil, tolprocarb,
acibenzolar-S-methyl, probenazole, tiadinil, isotianil,
laminarin, cymoxanil, fosetyl, teclofthalam, triazoxide,
flusulfamide, diclomezine, methasulfocarb, cyflufenamid,
10 metrafenone, pyriofenone, dodine, flutianil, ferimzone,
tebufloquin, validamycin, basic copper chloride, copper(II)
hydroxide, basic copper sulfate, Dodecylbenzenesulphonic
acid bisethylenediamine copper [II] salt (DBEDC)),
organocopper, sulfur, chlorothalonil, dichlofluanid,
15 tolylfluanid, guazatine, iminoctadine, anilazine, dithianon,
chinomethionat, fluoroimide, dipymetitrone, quinofumelin,
dichlobentiazox,
3-chloro-5-phenyl-6-methyl-4-(2,6-difluorophenyl)pyridadine
(1358061-55-8; hereinafter, referred to as fungicide
20 compound p6),
a compound represented by the following formula: 133
0
0H 0a N" N 0 0 00
(517875-34-2; hereinafter, referred to as fungicide
compound Q7),
N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5
5 yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N
methyimethaneimidamide (1202781-91-6; hereinafter, referred
to as fungicide compound P8),
4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3
dimethyl-1H-pyrazole-5-amine (1362477-26-6; hereinafter,
10 referred to as fungicide compound P9),
2,2-dimethy-9-fluoro-5-(quinolin-3-yl)-2,3
dihydrobenzo[f][1,4]oxazepine (1207749-50-5; hereinafter,
referred to as fungicide compound @10),
2-[6-(3-fluoro-4-methoxyphenyl)-4-methylpyridin-2
15 yl]quinazoline (1257056-97-5; hereinafter, referred to as
fungicide compound 311),
5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidineamine
(1174376-25-0; hereinafter, referred to as fungicide
compound P12),
20 5-flucro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine- 134
2(1H)-one (1616664-98-2; hereinafter, referred to as
fungicide compound P13),
N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N
methylmethaneimideamide (1052688-31-9; hereinafter,
5 referred to as fungicide compound P14),
N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}
N-ethyl-N-methylmethaneimideamide (929908-57-6; hereinafter,
referred to as fungicide compound 315),
ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6;
10 hereinafter, referred to as fungicide compound B16),
N-[(2-chlorothiazol-5-yl)methyl-N-ethyl-6-methoxy-3
nitropyridine-2-amine (1446247-98-8; hereinafter, referred
to as fungicide compound P17), and
1-{2-({[1-(4-chlorophenyl)-lH-pyrazol-3-yl]oxyfmethyl)-3
15 methylpenyl]-4-methyl-5-oxo-4,5-dihydro-lH-tetrazole
(1472649-01-6, hereinafter, referred to as fungicide
compound Pl8).
[0120]
Group (c) represents a plant growth modulating
20 ingredients group selected from the group consisting of the
following sub group c-1, sub group c-2, and sub group c-3.
Sub group c-1:
Plant growth modulating ingredients group selected from the
25 group consisting of ethephon, chlormequat, chlormequat- 135
chloride, mepiquat, mepiquat-chloride, Gibberellin A3,
abscisic acid, Kinetin, benzyladenine, forchlorfenuron, and
thidiazuron.
[0121]
5 Sub group c-2:
Mycorrhizal fungi group selected from the group consisting
of Glomus spp., Glomus intraradices, Glomus mosseae, Glomus
aggregatum, and Glomus etunicatuRm.
[0122]
10 Sub group c-3:
Root nodule bacteria group selected from the group
consisting of Bradyrhizobium elkani, Bradyrhizobium
japonicum, Bradyrhizobium lupini, Rhizobium leguminosarum
bv. trifolii, Rhizobium leguminosarun bv. phaseoli,
15 Rhizobium leguminosarun bv. viciae, Sinorhizobium meliloti,
and Rhizobium spp..
[0123]
Group (d):
Phytotoxicity-reducing ingredient group selected from the
20 group consisting of benoxacor, cloquintocet-mexyl,
cyometrinil, dichlormid, fenchlorazole-ethyl, fenclorim,
flurazole, furilazole, mefenpyr-diethyl, MG191 (2
(dichloromethyl)-2-methyl-1,3-dioxolane), oxabetrinil,
allidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofenim,
25 1,8-naphthalic anhydride, and AD-67 (4-(dichloroacetyl)-l- 136
oxa-4-azaspiro [4.5] decane).
[0124]
Examples of the combination of the present active
ingresient and the Present compound in the present
5 composition are described below. The symbol of "SX"
represents any one of the Present compound selected from
the compound group SX1 to the compound group SX18. Also,
all the below-mentioned present active ingredient are known
active ingredients, and are commercially available, may be
10 produced by the known method, or are available from the
bacterial authority depository.
[0125]
alanycarb + SX, aldicarb + SX, bendiocarb +
SXbenfuracarb + SX, butocarboxim + SX, butoxycarboxim + SX,
15 carbaryl: NAC + SX, carbofuran + SX, carbosulfan + SX,
ethiofencarb + SX, fenobucarb: BPMC + SX, formetanate + SX,
furathiocarb + SX, isoprocarb: MIPC + SX, methiocarb + SX,
methomyl + SX, metolcarb + SX, oxamyl + SX, pirimicarb + SX,
propoxur: PHC + SX, thiodicarb + SX, thiofanox + SX,
20 triazamate + SX, trimethacarb + SX, XMC + SX, xylylcarb +
SX;
[0126]
acephate + SX, azamethiphos + SX, azinphos-ethyl + SX,
azinphos-methyl + SX, cadusafos + SX, chlorethoxyfos + SX,
25 chlorfenvinphos + SX, chlormephos + SX, chlorpyrifos + SX, 137
chlorpyrifos-methyl + SX, coumaphos + SX, cyanophos: CYAP
+ SX, demeton-S-methyl + SX, diazinon + SX, dichlorvos:
DDVP + SX, dicrotophos + SX, dimethoate + SX,
dimethylvinphos + SX, disulfoton + SX, EPN + SX, ethion +
5 SX, ethoprophos + SX, famphur + SX, fenamiphos + SX,
fenitrothion: MEP + SX, fenthion: MPP + SX, fosthiazate +
SX, heptenophos + SX, imicyafos + SX, isofenphos + SX,
isopropyl-O-(methoxyaminothiophosphoryl)salicylate + SX,
isoxathion + SX, malathion + SX, mecarbam + SX,
10 methamidophos + SX, methidathion: DMTP + SX, mevinphos + SX,
monocrotophos + SX, naled: BRP + SX, omethoate + SX,
oxydemeton-methyl + SX, parathion + SX, parathion-methyl +
SX, phenthoate: PAP + SX, phorate + SX, phosalone + SX,
phosmet: PMP + SX, phosphamidon + SX, phoxim + SX,
15 pirimiphos-methyl + SX, profenofos + SX, propetamphos + SX,
prothiofos + SX, pyraclofos + SX, pyridaphenthion + SX,
quinalphos + SX, sulfotep + SX, tebupirimfos + SX, temephos
+ SX, terbufos + SX, tetrachlorvinphos + SX, thiometon + SX,
triazophos + SX, trichlorfon: DEP + SX, vamidothion + SX;
20 [0127]
ethiprole + SX, fipronil + SX, flufiprole + SX, chlordane +
SX, endosulfan + SX, alpha-endosulfan + SX;
[0128]
afoxolaner + SX, fluralaner + SX, broflanilide + SX,
25 fluxametamide + SX; 138
[0129]
acrinathrin + SX, allethrin + SX, bifenthrin + SX, kappa
bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX,
cycloprothrin + SX, cyfluthrin + SX, beta-cyfluthrin + SX,
5 cyhalothrin + SX, gamma-cyhalothrin + SX, lambda
cyhalothrin + SX, cypermethrin + SX, alpha-cypermethrin +
SX, beta-cypermethrin + SX, theta-cypermethrin + SX, zeta
cypermethrin + SX, cyphenothrin + SX, deltamethrin + SX,
empenthrin + SX, esfenvalerate + SX, etofenprox + SX,
10 fenpropathrin + SX, fenvalerate + SX, flucythrinate + SX,
flumethrin + SX, fluvalinate + SX, tau-fluvalinate + SX,
halfenprox + SX, heptafluthrin + SX, imiprothrin + SX,
kadethrin + SX, meperfluthrin + SX, momfluorothrin + SX,
permethrin + SX, phenothrin + SX, prallethrin + SX,
15 pyrethrins + SX, resmethrin + SX, silafluofen + SX,
tefluthrin + SX, kappa-tefluthrin + SX, tetramethrin + SX,
tetramethylfluthrin + SX, tralomethrin + SX, transfluthrin
+ SX, benfluthrin + SX, flufenoprox + SX, flumethrin + SX,
sigma-cypermethrin + SX, furamethrin + SX, metofluthrin +
20 SX, profluthrin + SX, dimefluthrin + SX, epsilon
metofluthrin + Sx, epsilon-momfluorothrin + Sx,
methoxychlor + SX;
[0130]
acetamiprid + SX, clothianidin + SX, dinotefuran + SX,
25 imidacloprid + SX, nitenpyram + SX, thiacloprid + SX, 139
thiamethoxam + SX, sulfoxaflor + SX, flupyradifurone + SX,
triflumezopyrim + SX, dicloromezotiaz + SX, cycloxaprid +
SX, insecticidal compound axl + SX;
[0131]
5 chlorantraniliprole + SX, cyantraniliprole + SX,
cycloniliprole + SX, flubendiamide + SX, tetraniliprole +
SX, cyhalodiamide + SX, insecticidal compound a2 + SX;
[0132]
Beauveria bassiana + SX, Beauveria bassiana strain GHA + SX,
10 Beauveria brongniartii + SX, Paecilomyces fumosoroseus + SX,
Paecilomyces lilacinus + SX, Paecilomyces tenuipes + SX,
Verticillium lecani + SX, Arthrobotrys dactyloides + SX,
Bacillus thuringiensis + SX, Bacillus firmus + SX, Bacillus
firmus strain CNCM 1-1582 + SX, Bacillus megaterium + SX,
15 Hirsutella rhossiliensis + SX, Hirsutella minnesotensis +
SX, Mbnacrosporium phymatopagus + SX, Pasteuria nishizawae
+ SX, Pasteuria penetrans + SX, Pasteuria usgae + SX,
Verticillium chlanydosporium + SX;
[0133]
20 abamectin + SX, fluazaindolizine + SX, fluensulfone + SX,
fluopyram + SX, tioxazafen + SX;
[0134]
spinetoram + SX, spinosad + SX, emamectin-benzoate + SX,
lepimectin + SX, milbemectin + SX, hydroprene + SX,
25 kinoprene + SX, methoprene + SX, fenoxycarb + SX, 140
pyriproxyfen + SX, methyl bromide + SX, chloropicrin + SX,
sulfuryl fluoride + SX, sodium aluminium fluoride or
chiolite + SX, borax + SX, boric acid + SX, disodium
octaborate + SX, sodium borate + SX, sodium metaborate + SX,
5 tartar emetic + SX, dazomet + SX, metam + SX, pymetrozine +
SX, pyrifluquinazone + SX, clofentezine + SX, hexythiazox +
SX, diflovidazin + SX, etoxazole + SX, diafenthiuron + SX,
azocyclotin + SX, cyhexatin + SX, fenbutatin oxide + SX,
propargite + SX, tetradifon + SX, chlorfenapyr + SX, DNOC +
10 SX, sulfluramid + SX, bensultap + SX, cartap + SX, cartap
hydrochloride + SX, thiocyclam + SX, thiosultap-disodium +
SX, thiosultap-monosodium + SX, bistrifluron + SX,
chlorfluazuron + SX, diflubenzuron + SX, fluazuron + SX,
flucycloxuron + SX, flufenoxuron + SX, hexaflumuron + SX,
15 lufenuron + SX, novaluron + SX, noviflumuron + SX,
teflubenzuron + SX, triflumuron + SX, buprofezin + SX,
cyromazine + SX, chromafenozide + SX, halofenozide + SX,
methoxyfenozide + SX, tebufenozide + SX, amitraz + SX,
hydramethylnon + SX, acequinocyl + SX, fluacrypyrim + SX,
20 bifenazate + SX, fenazaquin + SX, fenpyroximate + SX,
pyridaben + SX, pyrimidifen + SX, tebufenpyrad + SX,
tolfenpyrad + SX, rotenone + SX, indoxacarb + SX,
metaflumizone + SX, spirodiclofen + SX, spiromesifen + SX,
spirotetramat + SX, aluminium phosphide + SX, calcium
25 phosphide + SX, phosphine + SX, zinc phosphide + SX, 141
calcium cyanide + SX, potassium cyanide + SX, sodium
cyanide + SX, cyenopyrafen + SX, cyflumetofen + SX,
pyflubumide + SX, flonicamid + SX, azadirachtin + SX,
benzoximate + SX, bromopropylate + SX, chinomethionat + SX,
5 dicofol + SX, pyridalyl + SX, lime sulfur + SX, sulfur + SX,
machine oil + SX, nicotine + SX, nicotine-sulfate + SX,
afidopyropen + SX, flometoquin + SX, metoxadiazone + SX,
pyriminostrobin + SX, insecticidal compound a3 + SX,
insecticidal compound A4 + SX, insecticidal compound a5 +
10 SX;
[0135]
benalaxyl + SX, benalaxyl-M + SX, furalaxyl + SX, metalaxyl
+ SX, metalaxyl-M + SX, oxadixyl + SX, ofurace + SX;
[0136]
15 benomyl + SX, carbendazim + SX, fuberidazole + SX,
thiabendazole + SX, thiophanate + SX, thiophanate-methyl +
SX;
[0137]
ethaboxam + SX;
20 [0138]
benodanil + SX, flutolanil + SX, mepronil + SX, isofetamid
+ SX, fenfuram + SX, carboxin + SX, oxycarboxin + SX,
thifluzamide + SX, benzovindiflupyr + SX, bixafen + SX,
fluxapyroxad + SX, furametpyr + SX, isopyrazam + SX,
25 penflufen + SX, penthiopyrad + SX, sedaxane + SX, 142
pydiflumetofen + SX, boscalid + SX, pyraziflumid + SX,
fungicide compound pl + SX, fungicide compound 32 + SX,
fungicide compound P3 + SX, fungicide compound P4 + SX,
fungicide compound P5 + SX;
5 [0139]
azoxystrobin + SX, coumoxystrobin + SX, enoxastrobin + SX,
flufenoxystrobin + SX, picoxystrobin + SX, pyraoxystrobin +
SX, mandestrobin + SX, pyraclostrobin + SX, pyrametostrobin
+ Sx, triclopyricarb + Sx, kresoxim-methyl + SX,
10 trifloxystrobin + SX, dimoxystrobin + SX, fenaminstrobin +
SX, metominostrobin + SX, orysastrobin + SX, famoxadone +
SX, fluoxastrobin + SX, fenamidone + SX, pyribencarb + SX;
[0140]
cyazofamid + SX, amisulbrom + SX, binapacryl + SX,
15 meptyldinocap + SX, dinocap + SX, fluazinam + SX;
[0141]
silthiofam + SX;
[01421
cyprodinil + SX, mepanipyrim + SX, pyrimethanil + SX;
20 [0143]
fenpiclonil + SX, fludioxonil + SX;
[0144]
biphenyl + SX, chloroneb + SX, dicloran + SX, quintozene +
SX, tecnazene + SX, tolclofos-methyl + SX;
25 [01451 143
azaconazole + SX, bitertanol + SX, bromuconazole + SX,
cyproconazole + SX, difenoconazole + SX, diniconazole + SX,
diniconazole-M + SX, epoxiconazole + SX, etaconazole + SX,
fenbuconazole + SX, fluquinconazole + SX, flusilazole + SX,
5 flutriafol + SX, hexaconazole + SX, imibenconazole + SX,
ipconazole + SX, ipfentrifluconazole + SX,
mefentrifluconazole + SX, metconazole + SX, myclobutanil +
SX, penconazole + SX, propiconazole + SX, simeconazole + SX,
tebuconazole + SX, tetraconazole + SX, triadimefon + SX,
10 triadimenol + SX, triticonazole + SX, prothioconazole + SX,
triforine + SX, pyrifenox + SX, pyrisoxazole + Sx,
fenarimol + SX, nuarimol + SX, imazalil + SX, oxpoconazole
+ SX, oxpoconazole fumarate + SX, pefurazoate + SX,
prochloraz + SX, triflurnizole + SX;
15 [0146]
dimethomorph + SX, flumorph + SX, pyrimorph + SX,
benthiavalicarb + SX, benthivalicarb-isopropyl + SX,
iprovalicarb + SX, valifenalate + SX, mandipropamid + SX;
[0147]
20 oxathiapiprolin + SX;
[0148]
picarbutrazox + SX;
[0149]
ferbam + SX, mancozeb + SX, maneb + SX, metiram + SX,
25 propineb + SX, thiram + SX, zineb + SX, ziram + SX; 144
[0150]
captan + SX, captafol + SX, folpet + SX;
[0151]
Agrobacterium radiobactor + SX, Bacillus amyloliquefaciens
5 + SX, Bacillus amyloliquefaciens strain QST713 + SX,
Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus
amyloliquefaciens strain MBI600 + SX, Bacillus
amyloliquefaciens strain D74 + SX, Bacillus
amyloliquefaciens strain AT-332 + SX, Bacillus pumilus + SX,
10 Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain
QST2808 + SX, Bacillus subtilis + SX, Erwinia carotovora
(such as CGE234M403 stain) + SX, Pseudomonas fluorescens
(such as G7090 strain) + SX, Talaromyces flavus (such as
SAY-Y-94-01 strain) + SX, Trichoderma atroviride (such as
15 SKT-1 strain) + SX, Trichoderma harzianum + SX, Harpin
protein + SX;
[0152]
bupirimate + SX, dimethirimal + SX, ethirimol + SX,
hymexazole + SX, octhilinone + SX, oxolinic acid + SX,
20 diethofencarb + SX, zoxamide + SX, pencycuron + SX,
fluopicolide + SX, phenamacril + SX, diflumetorim + SX,
tolfenpyrad + SX, fentin acetate + SX, fentin chloride + SX,
fentin hydroxide + SX, ametoctradin + SX, blasticidin-S +
SX, kasugamycin + SX, streptomycin + SX, oxytetracycline +
25 SX, quinoxyfen + SX, proquinazid + SX, chlozolinate + SX, 145
dimethachlone + SX, iprodione + SX, procymidone + SX,
vinclozolin + SX, edifenphos + SX, iprobenfos + SX,
pyrazophos + SX, isoprothiolane + SX, etridiazole + SX,
iodocarb + SX, propamocarb + SX, prothiocarb + SX,
5 aldimorph + SX, dodemorph + SX, fenpropidin + SX,
fenpropimorph + SX, piperalin + SX, spiroxamine + SX,
tridemorph + SX, fenhexamid + SX, fenpyrazamine + SX,
pyributicarb + SX, naftifine + SX, terbinafine + SX,
polyoxins + SX, phthalide + SX, pyroquilon + SX,
10 tricyclazole + SX, carpropamid + SX, diclocymet + SX,
fenoxanil + SX, tolprocarb + SX, acibenzolar-S-methyl + SX,
probenazole + SX, tiadinil + SX, isotianil + SX, laminarin
+ SX, cymoxanil + SX, fosetyl + SX, teclofthalam + SX,
triazoxide + SX, flusulfamide + SX, diclomezine + SX,
15 methasulfocarb + SX, cyflufenamid + SX, metrafenone + SX,
pyriofenone + SX, dodine + SX, flutianil + SX, ferimzone +
SX, tebufloquin + SX, validamycin + SX, basic copper
chloride + SX, copper(II) hydroxide + SX, basic copper
sulphate + SX, Dodecylbenzenesulphonic acid
20 bisethylenediamine copper [III] salt (DBEDC) + SX,
organocopper + SX, sulfur + SX, chlorothalonil + SX,
dichlofluanid + SX, tolylfluanid + SX, guazatine + SX,
iminoctadine + SX, anilazine + SX, dithianon + SX,
chinomethionat + SX, fluoroimide + SX, dipymetitrone + SX,
25 quinofumelin + SX, dichlobentiazox + SX, fungicide compound 146
B6 + SX, fungicide compound B7 + SX, fungicide compound B8
+ SX, fungicide compound B9 + SX, fungicide compound B10 +
SX, fungicide compound B11 + SX, fungicide compound $12 +
SX, fungicide compound B13 + SX, fungicide compound B14 +
5 SX, fungicide compound B15 + SX, fungicide compound B16 +
SX, fungicide compound B17 + SX, fungicide compound B18 +
SX;
[01531
ethephon + SX, chlormequat + SX, chlormequat-chloride + SX,
10 mepiquat + SX, mepiquat-chloride + SX, Gibberellin A3 + SX,
abscisic acid + SX, Kinetin + SX, benzyladenine + SX,
forchlorfenuron + SX, thidiazuron + SX;
[0154]
Glomus spp. + SX, Glomus intraradices + SX, Glomus mosseae
15 + SX, Glomus aggregatum + SX, Glomus etunicatum + SX;
[0155]
Bradyrhizobium elkani + SX, Bradyrhizobium japonicum + SX,
Bradyrhizobium lupini + SX, Rhizobium leguminosarum bv.
trifolii + SX, Rhizobium leguminosarum bv. phaseoli + SX,
20 Rhizobium leguminosarum bv. viciae + SX, Sinorhizobium
meliloti + SX, Rhizobium spp. + SX;
[0156]
benoxacor + SX, cloquintocet-mexyl + SX, cyometrinil + SX,
dichlormid + SX, fenchlorazole-ethyl + SX, fenclorim + SX,
25 flurazole + SX, furilazole + SX, mefenpyr-diethyl + SX,
/ n n 1 /I 1 1 \ .nI I 147
MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane) + SX,
oxabetrinil + SX, allidochlor + SX, isoxadifen-ethyl + SX,
cyprosulfamide + SX, fluxofenim + SX, 1,8-naphthalic
anhydride + SX, AD-67 4-(dichloroacetyl)-1-oxa-4-azaspiro
5 [4.51 decane) + SX.
[0157]
In the composition of the present invention, the
weight ratio of the Present compound to the present active
ingredient includes, for example, usually within a range of
10 100:1 to 1:100, and preferably within a range of 10:1 to
1:10, when the present active ingredient is selected from
the above-mentioned Group (a), Group (c) or Group (d).
When the present active ingredient is selected from the
above-mentioned Group (b), the weight ratio of the Present
15 compound to the present active ingredient includes, for
example, usually within a range of 10,000:1 to 1:100, and
preferably within a range of 1,000:1 to 1:10.
[0158]
The compound of the present invention and the
20 composition of the present invention can be used to control
harmful arthropod. Examples of the harmful arthropod are
as follows.
[0159]
Hemiptera pests:
25 Delphacidae (for example, Laodelphax striatellus, 148
Nilaparvata lugens, Sogatella furcifera, or Peregrinus
maidis),
Deltocephalidae (for example, Nephotettix cincticeps,
Nephotettix virescens, Nephotettix nigropictus (Rice green
5 leafhopper), Recilia dorsalis, Empoasca onukii, Empoasca
fabae, Dalbulus maidis, Mahanarva posticata (Sugarcane
froghopper), Mahanarva fimbriolota (Sugarcane root
spittlebug), Cofana spectra, or Nephotettix nigropictus,
Recilia dorsalis),
10 Aphididae (for example, Aphis gossypii, P4yzus persicae,
Brevicoryne brassicae, Aphis spiraecola, Macrosiphum
euphorbiae, Aulacorthum solani, Rhopalosiphum padi,
Toxoptera citricidus, Hyalopterus pruni, Aphis glycines
Matsumura, Rhopalosiphum maidis, Tetraneura
15 nigriabdominalis, Viteus vitifoliae, Daktulosphaira
vitifoliae (Grape Phylloxera), Phylloxera devastatrix
Pergande (Pecan phylloxera), Phylloxera notabilis pergande
(Pecan leaf phylloxera), or Phylloxera russellae Stoetzel
(Southern pecan leaf phylloxera),
20 Pentatomidae (for example, Scotinophara lurida,
Scotinophara coarctata (Malayan rice black bug), Nezara
antennata, Eysarcoris parvus, Halyomorpha mista, Nezara
viridula, Euschistus hers (Brown stink bug), Nezara
viridula (Southern green stink bug), Piezodorus guildinii
25 (Red banded stink bug), Scaptocoris castanea (Burrower 149
brown bug), Oebalus pugnax, or Dichelops melacanthus),
Alydidae (for example, Riptortus clavetus, Leptocorisa
chinensis, Leptocorisa acuta, or Leptocorisa spp.),
Miridae (for example, Trigonotylus caelestialium,
5 Stenotus rubrovittatus, Lygus lineolaris, or Blissus
leucopterus leucopterus (Chinchi bug)),
Aleyrodidae (for example, Trialeurodes vaporariorum,
Bemisia tabaci, Dialeurodes citri, or Aleurocanthus
spiniferus),
10 Coccoidea (for example, Aonidiella aurantii,
Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens,
Icerya purchasi, Planococcus Kraunhiae, Pseudococcus
longispinis, Pseudaulacaspis Pentagona, or Brevennia rehi),
Psyllidae (for example, Diaphorina citri, Psylla
15 pyrisuga, Bactericerca cockerelli),
Tingidae (for example, Stephanitis nasi),
Cimicoidea (for example, Cimex lectularius),
Quesada gigas (Giant Cicada);
and the others.
20 [0160]
Lepidoptera pests:
Pyralidae (for example, Chilo suppressalis, Chilo
polychrysus (Darkheaded stm borer), Tryporyza incertulas,
Chilo polychrysus, Scirpophaga innotata, Scirpophaga
25 incertulas (Yellow stem borer), Sesamia inferens (Pink 150
borer), Rupela albinella, Cnaphalocrocis medinalis,
Marasmia patnalis, Marasmia exigna, Notarcha derogata,
Plodia interpunctella, Ostrinia furnacalis, Hellula undalis,
Pediasia teterrellus, Nymphula depunctalis, Marasmia spp.,
5 Hydraecia immanis (Hop vine borer), Ostrinia nubilalis
(European corn borer), Elasmopalpus lignosellus (Lesser
cornstalk borer), Epinotia aporema (Bean Shoot Borer),
Diatraea saccharalis (Sugarcane borer), Telchin licus
(Giant Sugarcane borer)),
10 Noctuidae (for example, Spodoptera litura, Spodoptera
exigua, Pseudaletia separata, Mamestra brassicae, Sesamia
inferens, Spodoptera mauritia, Spodoptera frugiperda,
Spodoptera exempta, Agrotis ipsilon, Plusia nigrisigna,
Pseudoplusia includens (Soybean looper), Trichoplusia spp.,
15 Heliothis spp. (for example, Heliothis virescens),
Helicoverpa spp. (for example, Helicoverpa armigera) ,
Anticarsia gammatalis (Velvetbean caterpillar), or Alabama
argillacea (Cotton leafworm)),
Pieridae (for example, Pieris rapae),
20 Adokisofiesu genus,
Tortricidae (for example, Grapholita molesta,
Leguminivora glycinivorella, Matsumuraeses azukivora,
Adoxophyes orana fasciata, Adoxophyes honmai, Homona
magnanima, Archips fuscocupreanus, or Cydia pomonella),
25 Gracillariidae (for example, Caloptilia theivora, or 151
Phyllonorycter ringoneella),
Carposinidae (for example, Carposina niponensis,
Ecdytolopha aurantiana (Citrus fruit borer)),
Lyonetiidae (for example, Leucoptera coffeela (Coffee
5 Leaf miner), or Lyonetia spp.)),
Lymantriidae (for example, Lymantria spp., or
Euproctis spp.),
Yponomeutidae (for example, Plutella xylostella),
Gelechiidae (for example, Pectinophora gossypiella, or
10 Phthorimaea operculella) ,
Arctiidae (for example, Hyphantria cunea);
and the others.
[0161]
Thysanoptera pests:
15 Thysanopterae (for example, Frankliniella occidentalis,
Thrips parmi, Scirtothrips dorsalis, Thrips tabaci,
Frankliniella intonsa, Frankliniella occidentalis,
Haplothrips aculeatus, Stenchaetothrips biformis);
and the others.
20
Diptera pests:
Diptera:
House mosquitoes (Culex spp.) (for example, Culex
pipiens pallens, Culex tritaeniorhynchus, or Culex
25 quinquefasciatus), 152
Aedes spp. (for example, Aedes aegypti, or Aedes
albopictus),
Anopheles spp. (for example, Anopheles sinensis),
Chironomidae,
5 Muscidae (for example, Musca domestica, or Muscina
stabulans),
Anthomyiidae (for example, Delia platura, Delia
antiqua, or Tetanops myopaeformis),
Agromyzidae (for example, Agromyza oryzae, Hydrellia
10 griseola, Liriomyza sativae, Liriomyza trifolii, or
Chromatomyia horticola),
Chloropidae (for example, Chlorops oryzae),
Tephritidae (for example, Dacus cucurbitae, or
Ceratitis capitaLa),
15 Ephydridae (for example, Hydrellia philippina, or
Hydrellia sasakii),
Drosophilidae,
Phoridae (for example, Megaselia spiracularis),
Psychodidae (for example, Clogmia albipunctata),
20 Sciaridae,
Cecidomyiidae (for example, Mayetiola destructor, or
Orseolia oryzae),
Diopsidae (for example, Diopsis macrophthalma),
Tipulidae (for example, Tipula oleracea (Common
25 cranefly), or Tipula paludosa (European cranefly)); 153
and the others.
[0162]
Coleoptera pests:
Chrysomelidae (for example, Diabrotica virgifera
5 virgifera, Diabrotica undecimpunctata howardi, Diabrotica
barberi, Diabrotica virgifera zeae, Diabrotica balteata
LeConte, Diabrotica speciosa, Diabrotica speciosa (Cucurbit
Beetle), Cerotoma trifurcata, Oulema melanopus, Aulacophora
femoralis, Phyllotreta striolata, Leptinotarsa decemlineata,
10 Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria,
Epitrix cucumeris, Dicladispa armigera, Stenolophus
lecontei (Seedcorn beetle), or Clivinia impressifrons
(Slender seedcorn beetle)),
Scarabaeidae (for example, Anomala cuprea, Anomala
15 rufocuprea, Popillia japonica, Rhizotrogus majalis
(European Chafer), Bothynus gibbosus (Carrot beetle),
Colaspis brunnea (Grape Colaspis), Myochrous denticollis
(southern Corn leaf beetle), Holotrichia spp., or
Phyllophaga spp. (for example, Phyllophaga crinita)),
20 Erirhinidae (for example, Sitophilus zeamais,
Echinocnemus squameus, Lissorhoptrus oryzophilus, or
Sphenophorus venatus),
Curculionidae (for example, Anthonomus grandis,
Sphenophorus callosus (Southern Corn Billbug), Sternechus
25 subsignatus (Soybean stalk weevil), or Sphenophorus spp. 154
(for example, Sphenophorus levis)),
Epilachna (for example, Epilachna vigintioctopunctata),
Scolytidae (for example, Lyctus brunneus, or Tomicus
piniperda),
5 Bostrichidae,
Ptinidae,
Cerambycidae (for example, Anoplophora malasiaca, or
Migdolus fryanus),
Elateridae (Agriotes sp., Aelous sp., Anchastus sp.,
10 Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp. )
(for example, Melanotus okinawensis, Agriotes ogurae
fuscicollis, or Melanotus legatus),
Staphylinidae (for example, Paederus fuscipes),
Hypothenemus hampei (Coffee Barry Borer);
15 and the others.
[0163]
Orthoptera pests:
Locusta migratoria, Gryllotalpa africana, Dociostaurus
maroccanus, Chortoicetes terminifera, Nomadacris
20 septemfasciata, Locustana pardalina (Brown Locust),
Anacridium melanorhodon (Tree Locust), Calliptamus italicus
(Italian Locust), Melanoplus differentialis (Differential
grasshopper), klanoplus bivittatus (Twostriped
grasshopper), Melanoplus sanguinipes (Migratory
25 grasshopper), Mlanoplus femurrubrum (Red-Legged 155
grasshopper), Camnula pellucida (Clearwinged grasshopper),
Schistocerca gregaria, Gastrimargus musicus (Yellow-winged
locust), Austracris guttulosa (Spur-throated locustt, Oxya
yezoensis, Oxya japonica, Patanga succincta, Grylloidea
5 (for example, Acheta domesticus, Teleogryllus emma, or
Anabrus simplex (Mormon cricket));
and the others.
Hymenoptera pests:
10 Tenthredinidae (for exmaple, Athalia rosae, or Athalia
japonica),
Solenopsis spp.,
Acromyrmex spp. (for example, Atta capiguara (Brown
leaf-cutting ant));
15 and the others.
[0164)
Blattariae pests:
Blattella germanica, Periplaneta fuliginosa,
Periplaneta americana, Periplaneta brunnea, Blatta
20 orientalis, and the others.
Isoptera pests:
Reticulitermes speratus, Coptotermes formosanus,
Incisitermes minor (Coptotermes formosanus), Cryptotermes
25 domesticus, Odontotermes formosanus, Neotermes koshunensis, 156
Glyptotermes satsumensis, Glyptotermes nakajimai,
Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes
kushimensis, Hodotermopsis sjostedti, Coptotermes
guangzhoensis, Reticulitermes amamianus, Reticulitermes
5 miyatakei, Reticulitermes kanmonensis, Nasutitermes
takasagoensis, Pericapritermes nitobei, Sinocapritermes
mushae, or Cornitermes cumulans);
and the others.
[0165]
10 Acarina pests:
Tetranychidae (for example, Tetranychus urticae,
Tetranychus kanzawai, Panonychus citri, Panonychus ulmi,
Oligonychus spp., or Brevipalpus phoenicis (Southern Turkey
spider mites)),
15 Eriophyidae (for example, Aculops pelekassi,
Phyllocoptruta citri, Aculops lycopersici, Calacarus
carinatus, Acaphylla theavagrans, Eriophyes chibaensis, or
Aculus schlechtendali),
Tarsonemidae (for example, Polyphagotarsonemus latus),
20 Tenuipalpidae (for Example, Brevipalpus phoenicis),
Tuckerellidae;
Ixodidae (for Example, Haemaphysalis longicornis,
Haemaphysalis flava, Dermacentor taiwanicus, Dermacentor
variabilis, Ixodes ovatus, Ixodes persulcatus, Ixodes
25 scapularis, Amblyomma americanum, Boophilus microplus, or 157
Rhipicephalus sanguineus),
Acaridae (for example, Tyrophagus putrescentiae, or
Tyrophagus similis) ,
Pyroglyphidae (for example, Dermatophagoides farinae,
5 or Dermatophagoides ptrenyssnus);
Cheyletidae (for example, Cheyletus eruditus,
Cheyletus malaccensis, or Cheyletus moorei);
Sarcoptidae (for example, Octodectes cynotis, or
Sacroptes scabiei),
10 Demodex folliculorum (for example, Demodex canis),
Listrophoridae,
Oribatid mites,
Dermanyssidae (for example, Ornithonyssus bacoti,
Ornithonyssus sylvairum, or Dermanyssus gallinae),
15 Trombiculid mites (for example, Leptotrombidium
akamushi),
and the others.
Araneae:
20 Chiracanthium japonicum, or Latrodectus hasseltii, and
the others.
Chilopoda:
Thereuonema hilgendorfi, or Scolopendra subspinipes,
25 and the others. 158
Diplopoda:
Oxidus gracilis, or Nedyopus tambanus, and the others,
5 Isopoda:
Armadillidium vulgare, and the others.
Gastropoda:
Limax marginatus, or Limax flavus, Pomacea
10 canaliculata, and the others.
[0166]
For example, when the present active ingredient is an
ingredient selected from the sub group a-9, the composition
of the present invention can be used to control harmful
15 nematodes. Also, for example, when the present active
ingredient is an ingredient selected from the sub group (b),
the composition of the present invention can be used to
control phytopathogenic fungus.
Examples of the harmful nematodes and the
20 phytopathogenic fungus include the followings.
[0167]
Harmful nematodes:
Aphelenchoides sp. (for example, Aphelenchoides basseyi);
Pratylenchus sp. (for example, Pratylenchus coffeae,
25 Pratylenchus brachyurus, Pratylenchus neglectus); 159
Meloidogyne sp. (for example, kloidogyne javanica,
Meloidogyne incognita, Meloidogyne hapla) ;
Heterodera sp. (for example, Heterodera glycines);
Globodera sp. (for example, Globodera rostochiensis);
5 Bursaphelenchus sp. (for example, Rotylenchulus reniformis,
Nothotylenchus acris, Radopholus similis, Ditylenchus
dipsaci, Tylenchulus semipenetrans, Longidorus sp.,
Xiphinema sp., Trichodorus sp., Bursaphelenchus
xylophilus);
10 [0168]
Rice diseases: blast (Jvfgnaporthe grisea), brown spot
(Cochliobolus miyabeanus), sheath blight (Rhizoctonia
solani), bakanae disease (Gibberella fujikuroi), and downy
mildew (Sclerophthora macrospora);
15 Wheat diseases: powdery mildew (Erysiphe graminis),
fusarium blight (Fusariun gaminearum, F. avenaceum, F.
culmorum, Microdochium nivale), rust (Puccinia striiformis,
P. graminis, P. recondite), snow mould (Nicronectriella
nivale, M. majus), typhulasnow blight (Typhula sp.), loose
20 smut (Ustilago tritici), stinking smut (Tilletia caries, T.
controversa), eyespot (Pseudocercosporella herpotrichoides),
leaf blotch (Septoria tritici), glume blotch (Stagonospora
nodorum), tan spot (Pyrenophora tritici-repentis),
rhizoctonia seeding blight (Rhizoctonia solani), and take
25 all disease (Gaeumannomyces graminis) 160
Barly diseases: powdery mildew (Erysiphe graninis),
fusarium blight (Fusarium gaminearum, F. avenaceum, F.
culmorum, Microdochium nivale), rust (Puccinia striiformis,
P. graminis, P. hordei), loose smut (Ustilago nuda), scald
5 (Rhynchosporium secalis), net blotch (Pyrenophora teres),
spot blotch (Cochliobolus sativus), leaf stripe
(Pyrenophora graminea), Ramularia disease (Ramularia collo
cygni), and rhizoctonia seeding blight (Rhizoctonia
solani);
10 Corn diseases: rust (Puccinia sorghi), southern rust
(Puccinia polysora), northern leaf blight (Setosphaeria
turcica), tropical rust (Physopella zeae), southern leaf
blight (Cochliobolus heterostrophus), anthracnose
(Colletotrichum gfaminicola), gray leaf spot (Cercospora
15 zeae-maydis), eyespot (Kabatiella zeae), phaeosphaeria leaf
spot (Phaeosphaeria maydis), diplomat over Deer disease
(Stenocarpella maydis, Stenocarpella macrospora), Stalk Rot
(Fusarium graminearum, Fusariumn verticilioides,
Colletotrichum graminicola), corn smut (Ustilago maydis);
20 Cotton diseases: anthracnose (Colletotrichum gossypii),
grey mildew (Ramuraria areola), alternaria leaf spot
(Alternaria macrospora, A. gossypii), Black root rot due to
Thielaviopsis spp. (Thielaviopsis basicola);
Coffee diseases: rust (Hemileia vastatrix), leaf spot
25 (Cercospora coffeicola); 161
Rape seed diseases: sclerotinia rot (Sclerotinia
sclerotiorum), black spot (Alternaria brassicae), and black
leg (Phoma lingam);
Sugarcane diseases: rust (Puccinia melanocephela,
5 Puccinia kuehnii), and smut (Ustilago scitaminea);
Sunflower diseases: rust (Puccinia helianthi), and
downy mildew (Plasmopara halstedii);
Citrus diseases: melanose (Diaporthe citri), scab
(Elsinoe fawcetti), fruit rot (Penicillium digitatum, P.
10 italicum), and epidemics (Phytophthora parasitica,
Phytophthora citrophthora);
Apple diseases: blossom blight (Monilinia mali),
canker (Valsa ceratosperma), powdery mildew (Podosphaera
leucotricha), alternaria leaf spot (Alternaria alternata
15 apple pathotype), scab (Venturia inaequalis), anthracnose
(Glomerella cingulata), brown spot (Diplocarpon mali), ring
spot (Botryosphaeria berengeriana), and epidemics
(Phytophtora cactorum);
Pear diseases: scab (Venturia nashicola, V. pirina),
20 black spot (Alternaria alternata Japanese pear pathotype)
and rust (Gymnosporangium haraeanum) ;
Peach diseases: brown rot (Mfonilinia fructicola), scab
(Cladosporium carpophilum) and Phomopsis rot (Phomopsis
sp.d)t;
25 Grapes diseases: anthracnose (Elsince ampelina) , ripe 162
rot (Glomerella cingulata), powdery mildew (Uncinula
necator), rust (Phakopsora ampelopsidis) , black rot
(Guignardia bidwellii), and downy mildew (Plasmopara
viticola);
5 Diseases of Japanese persimmon: anthracnose
(Gloeosporium kaki) and leaf spot (Cercospora kaki,
Mycosphaerella nawae)
Diseases of gourd family: anthracnose (Colletotrichum
lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy
10 stem blight (Didymella bryoniae) , target spot (Corynespora
cassiicola), fusarium wilt (Fusarium oxysporum), downy
mildew (Pseudoperonospora cubensis), epidemics
(Phytophthora sp.) and damping-off (Pythium sp.);
Tomato diseases: early blight (Alternaria solani),
15 leaf mold (Cladosporium fulvum), leaf mold
(Pseudocercospora fuligena), late blight (Phytophthora
infestans), and powdery mildew (Leveillula taurica);
Eggplant disease: brown spot (Phomopsis vexans) and
powdery mildew (Erysiphe cichoracearum);
20 Diseases of Cruciferous Vegetables: alternaria leaf
spot (Alternaria japonica), white spot (Cercosporella
brassicae), clubroot (Plasmodiophora parasitica), downy
mildew (Peronospora parasitica);
Welsh onion diseases: rust (Puccinia allii);
25 Soybean diseases: purple stain (Cercospora kikuchii), 163
sphaceloma scad (Elsinee glycines), pod and stem blight
(Diaporthe phaseolorum var. sojae), rust (phakopsora
pachyrhizi), target spot (Corynespora cassiicola),
anthracnose (Colletotrithum glycines, C. truncatum),
5 Rhizoctonia aerial blight (Rhizoctonia solani), septoria
brown spot (Septoria glycines), frog eye leaf spot
(Cercospora sojina), sclerotal disease (Sclerotinia
sclerotiorum), Powdery mildew (Microsphaera diffuse), Stem
plague (Phytophthora sojae), downy mildew (Peronospora
10 manshurica), sudden death (Fusarium virguliforme);
Kindney bean diseases: Crown rot (Sclerotinia
sclerotiorum), rust (Uromyces appendiculatus), angular leaf
spot (Phaeoisariopsis griseola), and anthracnose
(Colletotrichum lindernthianum);
15 Peanut diseases: early leaf spot (Cercospora
personata), late leaf spot (Cercospora arachidicola) and
southern blight (Sclerotiurn rolfsii);
Garden pea diseases: powdery mildew (Erysiphe pisi);
Potato diseases: early blight (Alternaria solani),
20 late blight (Phytophthora infestans), Pink rot
(Phytophthora erythroseptica), powdery scab (Spongospora
subterranean f. sp. subterranea), and verticillium wilt
(verticillium albo-atrum, V. dahliae, V. nigrescens) ;
Strawberry diseases: powdery mildew (Sphaerotheca
25 humuli); 164
Tea diseases: net blister blight (Exobasidium
reticulatum), white scab (Elsinoe leucospila), gray blight
(Pestalotiopsis sp.) and anthracnose (Colletotrichum theae
sinensis);
5 Tabacco diseases: brown spot (Alternaria longipes),
powdery mildew (Erysiphe cichoracearum), anthracnose
(Colletotrichum tabacum), downy mildew (Peronospora
tabacina), and epidemics (Phytophthora nicotianae);
Sugar beet diseases: cercospora leaf spot (Cercospora
10 beticola), leaf blight (Thanatephorus cucumeris), root rot
(Thanatephorus cucumeris) and aphanomyces root rot
(Aphanomyces cochlioides);
Rose diseases: black spot (Diplocarpon rosae) and
powdery mildew (Sphaerotheca pannosa);
15 Diseases of Chrysanthemum: leaf blight (Septoria
chrysanthemi-indici) and white rust (Puccinia horiana);
Onion diseases: botrytis leaf blight (Botrytis cinerea,
B. byssoidea, B. squamosa), gray-mold neck rot (Botrytis
alli), and small sclerotial rot (Botrytis squamosa);
20 Various crops diseases: gray mold (Botrytis cinerea),
and sclerotinia rot (Sclerotinia sclerotiorum);
Diseases of Japanese radish: alternaria leaf spot
(Alternaria brassicicola);
Turfgrass diseases: dollar spot (Sclerotinia
25 homeocarpa), brown patch and large patch (Rhizoctonia 165
solani); and
Banana diseases: Sigatoka disease (Vycosphaerella
fijiensis, Mlycosphaerella musicola);
Seed diseases or diseases in the early stages of the
5 growth of various plants caused by bacteria of Aspergillus
spp., Penicillium spp., Fusarium spp., Gibberella spp.,
Tricoderma spp., Thielaviopsis spp., Rhizopus spp., Mucor
spp., Corticium spp., Phoma spp., Rhizoctonia spp., and
Diplodia spp.; and
10 Viral diseases of various plants mediated by Polymixa
genus or Olpidium genus.
Burkholderia plantarii of rice (Burkholderia
plantarii); Angular Leaf Spot of Cucumber (Pseudomonas
syringae pv. Lachrymans); wilt disease of eggplant
15 (Ralstonia solanacearum); Citrus Canker (Xanthomonas
citiri); and Sof rot of white cabbage (Erwinia carotovora).
[0169]
The harmful arthropods, harmful nematodes and
phytopathogenic fungus may be harmful arthropods, harmful
20 nematodes or phytopathogenic fungus whose the sensitivity
to any of the present active ingredient is lowered or whose
the resistance against the present active ingredient is
developed.
[0170)
25 The compound of the present invention or the 166
composition of the present invention can be used to protect
plants from the plant diseases caused by insect-mediated
viruses.
[0171]
5 Examples of the plant diseases caused by the insect
mediated viruses on which the compound of the present
invention or the composition of the present invention has a
control efficacy include as follows.
[0172]
10 Rice dwarf disease (Rice waika virus), Rice tungro
disease (Rice tungro spherical virus, Rice tungro
bacilliform virus), Rice grassy stunt disease (Rice grassy
stunt virus), Rice ragged stunt disease (Rice ragged stunt
virus), Rice stripe disease (Rice stripe virus), Rice black
15 streaked dwarf disease (Rice black streaked dwarf virus),
Southern rice black-streaked dwarf disease (Southern rice
black-streaked dwarf virus), Rice gall dwarf disease (Rice
gall dwarf virus), Rice hoja blanca disease (Rice hoja
blanca virus), White leaf desease of rice (Rice white leaf
20 virus), Yellow dwarf disease (Yellow dwarf virus), Red
disease (Rice penyakit merah virus), Rice yellow stunt
disease (Rice yellow stunt virus), Rice transitory
yellowing disease (Rice transitory yellowing virus), Rice
Yellow Mottle disease (Rice Yellow Mottle Virus), Rice
25 necrosis mosaic disease (Rice necrosis mosaic virus), Rice 167
dwarf stunt disease (Rice dwarf stunt virus),
Wheat northern cereal mosaic disease (Northern Cereal
Mosaic Virus), Barley Yellow Dwarf disease (Barley Yellow
Dwarf Virus), Wheat yellow dwarf disease (Wheat yellow
5 dwarf virus), Oat sterile dwarf disease (Oat sterile dwarf
virus), Wheat streak mosaic disease (Wheat streak mosaic
virus);
Maize dwarf mosaic disease (Maize dwarf mosaic virus),
Maize stripe disease (maize stripe tenuivirus), Maize
10 chlorotic dwarf disease (Maize chlorotic dwarf virus),
Maize chlorotic mottle disease (maize chiorotic mottle
virus), Maize rayado fino disease (maize rayado fino
marafivirus), Corn stunt disease (Corn stunt spiroplasma),
Maize bushy stunt disease (Maize bushy stunt phytoplasma);
15 Sugarcane mosaic disease (Sugarcane mosaic virus);
Soybean mild mosaic disease (Soybean mild mosaic
virus), Mosaic disease (Alfalfa Mosaic Virus, Bean yellow
spot mosaic virus, Soybean mosaic virus, Bean yellow mosaic
virus, Cowpea severe mosaic virus), bean virus disease
20 (Broad bean wilt virus, Bean common mosaic virus, Peanut
stunt virus, Southern bean mosaic virus), Soybean dwarf
disease (Soybean dwarf luteovirus, Milk-vetch dwarf
luteovirus), Bean-pod mottle disease (Bean-pod mottle
virus), Brazilian bud blight disease (Tobbaco streak virus),
25 Cowpea chlorotic mottle disease (Cowpea chlorotic mottle), 168
Mung bean yellow mosaic disease (Mung bean yellow mosaic
virus), Peanut stripe disease (Peanut stripe mottle),
Soybean crinkle leaf disease (Soybean crinkle leaf virus),
Soybean severe stunt disease (Soybean severe stunt virus);
5 Tomato yellow leaf disease (Tomato chlorosis virus),
Tomato spotted wilt disease (Tomato spotted wilt virus),
Tomato yellow leaf curl disease (Tomato yellow leaf curl
virus), Melon spotted wilt disease (Melon yellow spot
virus), Watermelon mosaic disease (Watermelon mosaic virus),
10 Dwarf disease (Cucumber mosaic virus), Zucchini yellow
mosaic disease (Zucchini yellow mosaic virus), Turnip
mosaic disease (Turnip mosaic virus), Cucurbit chlorotic
yellow disease (Cucurbit chlorotic yellows virus), Capsicum
chlorosis disease (Capsicum chlorosis virus), Beet pseudo
15 yellow disease (Beet pseudo yellows virus);
chrysanthemum stem necrosis disease (chrysanthemum
stem necrosis virus), Impatiens necrotic spot disease
(Impatiens necrotic spot virus), Iris yellow spot disease
(Iris yellow spot virus);
20 Sweet potato mottle mosaic disease (Sweet potato
internal cork virus), Sweet potato shukuyo mosaic disease
(Sweet potato shukuyo mosaic virus); and
Mosaic virus diseases of various plants mediated by
Polymixa spp. or Olpidium spp.
25 169
[0173]
The agent for controlling harmful arthropods of the
present invention comprises the compound of the present
invention or the composition of the present invention and
5 an inert active carrier. The agent for controlling harmful
arthropods is usually prepared by mixing the compound of
the present invention or the composition of the present
invention with an inert active carrier such as solid
carrier, liquid carrier or gaseous carrier, and if
10 necessary, adding surfactants and the other auxiliary
agents for formulation, to formulate into emulsifiable
concentrates, oil solutions, dust formulations, granules,
wettable powders, flowables, microcapsules, aerosols,
smoking agents, poison baits, resin formulations, shampoo
15 formulations, paste-like formulations, foams, carbon
dioxide formulations and tablets and the others. Such
formulations may be processed into mosquito repellent coils,
electric mosquito repellent mats, liquid mosquito
formulations, smoking agents, fumigants, sheet formulations,
20 spot-on formulations or formulations for oral treatment.
Also, the agent for controlling harmful arthropods of the
present invention may be mixed with other pesticides,
miticides, nematicides, fungicides, plant growth regulators,
herbicides, and synergists.
25 The agent for controlling harmful arthropods of the 170
present invention comprises usually 0.01 to 95% by weight
of the compound of the present invention or the composition
of the present invention.
The formulation comprising the compound of the present
5 invention and the formulation comprising the active
ingredient of the present invention can be mixed, and then
used as a mixture thereof.
[0174]
Examples of the solid carrier to be used in the
10 formulation include fine powders or granules of clays (for
example, kaolin clay, diatomaceous earth, bentonite,
Fubasami clay, or acid white clay), synthetic hydrated
silicon oxides, talcs, ceramics, other inorganic minerals
(for example, sericite, quartz, sulfur, active carbon,
15 calcium carbonate or hydrated silica) or chemical
fertilizers (for example, ammonium sulfate, ammonium
phosphate, ammonium nitrate, urea or ammonium chloride) and
the others; as well as synthetic resins (for Example,
polyester resins such as polypropylene, polyacrylonitrile,
20 polymethylmethacrylate and polyethylene terephthalate;
nylon resins (for Example, nylon-6, nylon-li and nylon-66);
polyamide resins; polyvinyl chloride, polyvinylidene
chloride, vinyl chloride-propylene copolymers, and the
others).
25 [0175] 171
Examples of the above-mentioned liquid carriers
include water; alcohols (for example, methanol, ethanol,
isopropyl alcohol, butanol, hexanol, benzyl alcohol,
ethylene glycol, propylene glycol or phenoxy ethanol);
5 ketones (for Example, acetone, methyl ethyl ketone or
cyclohexanone); aromatic hydrocarbons (for example, toluene,
xylene, ethyl benzene, dodecyl benzene, phenyl xylyl ethane
or methylnaphthalene); aliphatic hydrocarbons (for example,
hexane, cyclohexane, kerosene or light oil); esters (for
10 example, ethyl acetate, butyl acetate, isopropyl myristate,
ethyl oleate, diisopropyl adipate, diisobutyl adipate or
propylene glycol monomethyl ether acetate); nitriles (for
Example, acetonitrile or isobutyronitrile); ethers (for
example, diisopropyl ether, 1,4-dioxane, ethyleneglycol
15 dimethyl ether, diethyleneglycol dimethyl ether, diethylene
glycol monomethyl ether, propylene glycol monomethyl ether,
dipropylene glycol monomethyl ether or 3-methoxy-3-methyl
1-butanol); acid amides (for example, dimethylformamide or
dimethylacetamide); halogenated hydrocarbons (for example,
20 dichloromethane, trichloroethane or carbon tetrachloride);
sulfoxides (for example, dimethyl sulfoxide); propylene
carbonate; and vegetable oils (for example, soybean oil or
cottonseed oil).
[0176]
25 Examples of the above-mentioned gaseous carrier 172
include fluorocarbon, butane gas, liquefied petroleum gas
(LPG), dimethyl ether, and carbon dioxide gas.
[0177]
Examples of the surfactants include nonionic
5 surfactants such as polyoxyethylenated alkyl ethers,
polyoxyethylenated alkyl aryl ethers and polyethylene
glycol fatty acid esters; and anionic surfactants such as
alkyl sulfonates, alkylbenzene sulfonates and alkyl
sulfates.
10 [0178]
Examples of the other auxiliary agents for formulation
include a binder, a dispersant, a colorant and a stabilizer.
Specific examples include casein, gelatin, polysaccharides
(for example, starch, gum arabic, cellulose derivatives and
15 alginic acid), lignin derivatives, bentonite, water-soluble
synthetic polymers (for example, polyvinyl alcohol,
polyvinyl pyrrolidone and polyacrylic acids), PAP (acidic
isopropyl phosphate), BHT (2,6-di-tert-butyl-4
methylphenol), BHA (a mixture of 2-tert-butyl-4
20 methoxyphenol and 3-tert-butyl-4-methoxyphenol).
[0179)
Examples of base material of the resin formulation
include polyvinyl chloride polymers, polyurethane and the
others, and a plasticizer such as phthalate esters (for
25 example, dimethyl phthalate, dioctyl phthalate), adipic 173
acid esters and stearic acid may be added to these base
materials, if necessary. The resin formulation can be
prepared by mixing the compound of the present invention
with the above-mentioned base material, kneading the
5 mixture, followed by molding it by injection molding,
extrusion molding or pressure molding and the like. The
resultant resin formulation can be subjected to further
molding or cutting procedure and the like, if necessary, to
be processed into shapes such as a plate, film, tape, net
10 or string shape. These resin formulations can be processed
into animal collars, animal ear tags, sheet products, trap
strings, gardening supports and other products.
Examples of a base material for the poison baits
include bait ingredients such as grain powder, vegetable
15 oil, saccharide and crystalline cellulose, and if necessary,
with addition of antioxidants such as dibutylhydroxytoluene
and nordihydroguaiaretic acid, preservatives such as
dehydroacetic acid, accidental ingestion inhibitors for
children and pets such as a chili powder, insect attraction
20 fragrances such as cheese flavor, onion flavor and peanut
oil.
[0180]
The method for controlling harmful arthropods of the
present invention is conducted by applying an effective
25 amount of the compound of the present invention or the 174
composition of the present invention to a harmful arthropod
directly and/or a habitat thereof (for example, plant
bodies, soil, an interior of a house, animal bodies). In
the method for controlling harmful arthropods of the
5 present invention, the Present compound is usually used in
the form of a harmful arthropod controlling agent.
[0181]
When an agent for controlling harmful arthropods of
the present invention is used for controlling harmful
10 arthropods in an agricultural field, the application dose
as an amount of the compound of the present invention or a
total amount of the compound of the present invention and
the active ingredient of the present invention is usually
2 within a range from 1 to 10,000 g per 10, 000 m . The
15 emulsifiable concentrate, the wettable powder, or the
flowable formulation etc. of an agent for controlling
harmful arthropods of the present invention is usually
applied by diluting it with water in such a way that a
concentration of the compound of the present invention or a
20 total concentration of the compound of the present
invention and the active ingredient of the present
invention is within a range from 0.01 to 10,000 ppm. The
granular formulation, or the dust formulation etc., is
usually applied as itself without diluting it.
25 [0182] 175
When the agent for controlling harmful arthropods of
the present invention is used to control harmful arthropods
that live inside a house, the application dose as an amount
of the Present compound is usually within a range from 0.01
5 to 1,000 mg per 1 m2 of an area to be treated, in the case
of using it on a planar area. In the case of using it
spatially, the application dose as an amount of the Present
compound is usually within a range from 0.01 to 500 mg per
1 m3 of the space to be treated. When the agent for
10 controlling harmful arthropods of the present invention is
formulated into emulsifiable concentrates, wettable powders,
flowables or the others, such formulations are usually
applied after diluting it with water in such a way that a
concentration of the active ingredient is within a range
15 from 0.1 to 10,000 ppm, and then sparging it. In the case
of being formulated into oil solutions, aerosols, smoking
agents, poison baits and the others, such formulations are
used as itself without diluting it.
[0183)
20 When the agent for controlling harmful arthropods of
the present invention is sued for controlling external
parasites of livestock such as cows, horses, pigs, sheep,
goats and chickens and small animals such as dogs, cats,
rats and mice, the pest control agent of the present
25 invention can be applied to the animals by a known method 176
in the veterinary field. Specifically, when systemic
control is intended, the pest control agent of the present
invention is administered to the animals as a tablet, a
mixture with feed or a suppository, or by injection
5 (including intramuscular, subcutaneous, intravenous and
intraperitoneal injections). On the other hand, when non
systemic control is intended, the pest control agent of the
present invention is applied to the animals by means of
spraying of the oil solution or aqueous solution, pour-on
10 or spot-on treatment, or washing of the animal with a
shampoo formulation, or by putting a collar or ear tag made
of the resin formulations to the animal. In the case of
administering to an animal body, the dose of the Present
compound is usually within a range from 0.1 to 1,000 mg per
15 1 kg of an animal body weight.
[0184]
The method for controlling harmful arthropods of the
present invention is carried out by applying an effective
amount of the compound of the present invention or the
20 composition of the present invention directly to harmful
arthropods, and/or habitats of harmful arthropods.
Examples of the habitats of harmful arthropods include
plants, soils for cultivating plants, houses, and animals.
[01851
25 Examples of applying an effective amount of the 177
compound of the present invention or the composition of the
present invention to plant or soils for cultivating plants
include a method of applying an effective amount of the
compound of the present invention or the composition of the
5 present invention to a stem and leaf, a flower, a seedling,
an ear of a plant; a method of applying an effective amount
of the compound of the present invention or the composition
of the present invention to a seed or a bulb such as seed
tuber (for example, a seed disinfection , a seed soaking,
10 or a seed coating), or a method of applying an effective
amount of the compound of the present invention or the
composition of the present invention to soils before
planting plants or soils after planting plants.
[0156]
15 Specific examples of applying an effective amount of
the compound of the present invention or the composition of
the present invention to a stem and leaf, a flower, a
seedling, an ear of a plant include a method for applying
an effective amount of the compound of the present
20 invention or the composition of the present invention to a
surface of a plant (for example, foliage application, and
trunk application), a method for applying an effective
amount of the compound of the present invention or the
composition of the present invention to a flower or a whole
25 plant at flowering times including before flowering, during 178
flowering, and after flowering, and a method for applying
an effective amount of the compound of the present
invention or the composition of the present invention to an
ear or a whole grain at sprouting season of grain.
5 (0187)
Examples of a method of controlling harmful arthropods
by applying an effective amount of the compound of the
present invention or the composition of the present
invention soils before planting plants or after planting
10 plants include a method of applying an effective amount of
a composition of the present invention to a root part of a
crop to be protected from damage such as ingestion by
harmful arthropods, and a method of controlling harmful
arthropods that ingest a plant by permeating and
15 transferring an effective amount of the composition of the
present invention from a root into the interior of the
plant body.
[0188]
Examples of the method of applying an effective amount
20 of the compound of the present invention or the composition
of the present invention to soils before planting plants or
after planting plants include planting hole treatment
(spraying into planting holes, soil mixing after planting
hole treatment), plant foot treatment (plant foot spraying,
25 soil mixing after plant foot treatment, irrigation at plant 179
foot, plant foot treatment at a later seeding raising
stage), planting furrow treatment (planting furrow spraying,
soil mixing after planting furrow treatment), planting row
treatment (planting row spraying, soil mixing after
5 planting row treatment, planting row spraying at a growing
stage), planting row treatment at the time of sowing
(planting row spraying at the time of sowing, soil mixing
after planting row treatment at the time of sowing),
broadcast treatment (overall soil surface spraying, soil
10 mixing after broadcast treatment), side-article treatment,
treatment of water surface (application to water surface,
application to water surface after flooding), other soil
spraying treatment (spraying of a granular formulation on
leaves at a growing stage, spraying under a canopy or
15 around a tree stem, spraying on the soil surface, mixing
with surface soil, spraying into seed holes, spraying on
the ground surfaces of furrows, spraying between plants),
other irrigation treatment (soil irrigation, irrigation at
a seedling raising stage, drug solution injection treatment,
20 irrigation of a plant part just above the ground, drug
solution drip irrigation, chemigation), seedling raising
box treatment (spraying into a seedling raising box,
irrigation of a seedling raising box, flooding into a
seedling raising box with drug solution), seedling raising
25 tray treatment (spraying on a seedling raising tray, 180
irrigation of a seedling raising tray, flooding into a
seedling raising tray with drug solution), seedbed
treatment (spraying on a seedbed, irrigation of a seedbed,
spraying on a lowland rice nursery, immersion of seedlings),
5 seedbed soil incorporation treatment (mixing with seedbed
soil, mixing with seedbed soil before sowing, spraying at
sowing before covering with soils, spraying at sowing after
covering with soils, mixing with covering soil, and other
treatment (mixing with culture soil, plowing under, mixing
10 with surface soil, mixing with soil at the place where
raindrops fall from a canopy, treatment at a planting
position, spraying of a granule formulation on flower
clusters, mixing with a paste fertilizer).
(0189]
15 In a step of applying to a seed or a bulb, a seed
described herein represents a seed of a plant at the state
before seeding to a soil or a culture medium for
cultivating a seed, and a bulb described herein represents
discoid stems, corms, rhizomes, tubers, tuberous, seed
20 tubers, and tuberous roots of a plant at the state before
planting in a soil or a culture medium for cultivating. A
method for controlling harmful arthropods by applying an
effective amount of the compound of the present invention
or the composition of the present invention into a seed or
25 a bulb include a method of applying an effective amount of 181
the compound of the present invention or the composition of
the present invention directly into a seed or a bulb of a
plant to be protected from damage such as ingestion by
harmful arthropods; and a method for controlling harmful
5 arthropods that ingest a seed by applying an effective
amount of the compound of the present invention or the
composition of the present invention in the vicinity of a
seed or a bulb; and a method for controlling harmful
arthropods that ingest a plant by permeating and
10 transferring an effective amount of the compound of the
present invention or the composition of the present
invention from a seed or a bulb into the interior of the
plant body. Examples of a method of applying an effective
amount of the compound of the present invention or the
15 composition of the present invention to a seed or a bulb
include spraying treatment, spray coating treatment,
immersion treatment, impregnation treatment, coating
treatment, film coating treatment, and pellet coating
treatment, and these methods can provide a preparation of a
20 seed or a bulb that retain an effective amount of the
composition of the present invention or the composition of
the present invention on the surface and/or into the
interior thereof.
[0190]
25 When the compound of the present invention or the 182
composition of the present invention are applied to a seed
or a bulb, an effective amount of the compound of the
present invention is usually within a range of 0.001 to
100g, preferably within a range of 0.02 to 20 g, based on 1
5 kg of the seed or the bulb. Also an effective amount of
the composition of the present invention is usually within
a range of 0.000001 to 50 g, preferably within a range of
0.0001 to 30 g of a total amount of the compound of the
present invention and the active ingredient of the present
10 invention, based on 1 kg of the seed or the bulb.
[0191]
The plants to which the compound of the present
invention and the composition of the present invention can
be applied include the followings.
15 Crops:
corn, rice, wheat, barley, rye, triticale, oat, sorghum,
cotton, soybean, peanut, arachis, common bean (kidney bean),
lima bean, adzuki bean, cowpea, mung bean, urd bean,
scarlet runner bean, rice bean, moth bean, tepary bean,
20 broad bean, pea, chick pea, lentils, lupin, pigeon pea,
alfalfa, buckwheat, beet, rape, sunflower, sugarcane,
tobacco, and the others;
Vegetables:
25 solanaceous vegetables (for example, eggplant, tomato, 183
pimento, pepper, bell pepper and potato),
cucurbitaceous vegetables (for example, cucumber, pumpkin,
zucchini, water melon, melon, and squash),
cruciferous vegetables (for example, Japanese radish, white
5 turnip, horseradish, kohlrabi, Chinese cabbage, cabbage,
leaf mustard, broccoli and cauliflower),
asteraceous vegetables (for example, burdock, crown daisy,
artichoke and lettuce),
liliaceous vegetables (for example, green onion, onion,
10 garlic and asparagus),
ammiaceous vegetables (for example, carrot, parsley, celery
and parsnip),
chenopodiaceous vegetables (for example, spinach and Swiss
chard),
15 lamiaceous vegetables (for example, Perilla frutescens,
mint, basil, and lavender),
strawberry, sweet potato, Dioscorea japonica, colocasia,
and the others;
20 Fruits:
pomaceous fruits (for example, apple, pear, Japanese pear,
Chinese quince and quince),
stone fleshy fruits (for example, peach, plum, nectarine,
Prunus mume, cherry fruit, apricot and prune),
25 citrus fruits (for example, Citrus unshiu, orange, lemon, 184
lime and grapefruit),
nuts (for example, chestnut, walnuts, hazelnuts, almond,
pistachio, cashew nuts and macadamia nuts),
berry fruits (for example, blueberry, cranberry, blackberry
5 and raspberry),
grape, kaki persimmon, olive, Japanese plum, banana, coffee,
date palm, coconuts,
and the others;
10 tea, mulberry,
flowering plant,
roadside trees (for example, ash, birch, dogwood,
Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar,
Judas tree, Liquidambar formosana, plane tree, zelkova,
15 Japanese arborvitae, fir wood, hemlock, juniper, Pinus,
Picea, and Taxus cuspidate),
flowers,
ornamental foliage plants,
sods, and
20 grasses.
(0192]
The plants described above are not limited
specifically, as long as they are breeds that are usually
cultivated.
25 [0193] 185
The plant described above may be plants that are bred
by a hybrid technology.
the plants that are bred by a hybrid technology is a first
5 generation hybrid that is produced by breeding two kinds of
different lines of breed variety, and generally speaking,
are plants having a heterosis having superior characters to
those of both parents breeds (in general, for example, it
leads to enhancement of yield potential and improvement of
10 resistance to biological and abiotic stress factors).
[0194]
The plants described above may include genetically
modified crop.
[0195]
15 For example, the genetically-modified crop described
above include also plants having resistance to herbicides
including HPPD (that is, 4-hydroxyphenylpyruvate
dioxygenase) inhibitors such as isoxaflutole; ALS (that is,
acetoacetate synthase) inhibitors such as imazethapyr and
20 thifensulfuron methyl; EPSP (that is, 5
enolpyruvoylshikimate-3-phosphate synthase) inhibitors;
glutamine synthetase inhibitors; PPO (that is,
protoporphyrinogen oxidase) inhibitors; bromoxynil; dicamba,
and the like, which resistance has been imparted by a
25 classical breeding method or gene recombination technology. (0196)
The plants described above may include plants that
have become capable of synthesizing selective toxins and
the like (for example, genus Bacillus such as Bacillus
5 thuringiensis) produced by using a gene recombination
technology; and the plants being capable of synthesizing a
gene segment that match partially an endogenous gene
derived from a harmful insect and also impart with specific
insecticidal activity by inducing a gene silencing (RNAi;
10 RNA interference) in a target harmful insect.
[0197]
In addition, the plants described above include lines
having two or more types of characters related to herbicide
resistance, pest resistance, disease resistance, and the
15 like as described above, which characters are imparted
using a classical breeding technology or gene recombination
technology, and lines having two or more types of
properties possessed by parent lines, which properties are
imparted by crossing genetically-engineered plants having
20 the same or different types of properties. Examples of
such plants include Smart stax (registered trademark).
EXAMPLES
[0198]
25 The following Examples including Preparation examples, 187
Formulation examples and Test examples, serve to illustrate
the present invention in more detail, which should not
intend to limit the present invention.
First, regarding the preparation of the compound of
5 the present invention, the Preparation Examples are shown
below.
[0199]
Preparation example 1
To a mixture of 2,5-dichloropyrazine 3.0 g, sodium
10 hydride (60 %, oily) 880 mg, and NMP 50 mL was added benzyl
alcohol 2.3 g under ice-cooling. The reaction mixtures
were raised to room temperature, and the resulting mixtures
stirred at room temperature for 5 hours. To the resulting
reaction mixtures was added water, and the mixtures were
15 extracted with ethyl acetate. The resulting organic
mixtures were washed with saturated brine, and dried over
anhydrous sodium sulfate, and concentrated under reduced
pressure. The resulting residues were subjected to a
silica gel column chromatography to give an intermediate
20 compound 1 represented by the following formula 3.1 g.
N O\/CI IN/
Intermediate compound 1
'H-NMR (CDCl3 ) 5: 8.12 (1H, d), 8.06 (1H, d), 7.46-7.33 (5H,
m), 5.37 (2H, s).
/ n n 1 /I 1 1 \ .nI I 188
[0200]
Preparation example 2
The mixture of the intermediate compound 1 3.1 g,2-[2
fluoro-4-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3
5 2-dioxaborolane 4.1 g,
tetrakis(triphenylphosphine)palladium(0)
820 mg, and 2M aqueous sodium carbonate solution 18 mL and
dimethoxyethane 60 mL was heated at 800C with stirring for
3 hours. The resulting reaction mixtures were allowed to
10 stand to room temperature, and to the mixtures was added
water, and the mixtures were extracted with ethyl acetate.
The resulting organic layers were washed with saturated
brine, dried over anhydrous sodium sulfate and concentrated
under reduced pressure. The resulting residues were
15 subjected to a silica gel column chromatography to give an
intermediate compound 2 represented by the following
formula 3.2 g.
FCF3 N
Intermediate compound 2
20 'H-NMR (CDCl3 ) 5: 8.69 (1H, dd), 8.40 (1H, d), 8.15 (1H, d),
7.56-7.33 (7H, m), 5.46 (2H, s).
[0201]
Preparation example 3
/ n n 1 /I 1 1 \ .nI I 189
The mixture of the intermediate compound 2 3.2 g,
ethanethiol 680 mg, sodium hydride (60 %, oily) 440 mg, and
NMP 40 mL was stirred at room temperature for 4 fours. To
the resulting reaction mixtures was added water, and the
5 mixtures were extracted with ethyl acetate. The resulting
organic layers were washed with saturated brine, dried over
anhydrous sodium sulfate, and coSoncentrated under reduced
pressure. The resulting residues were dissolved into
chloroform 50 mL, and to the mixtures was added mCPA (75 %)
10 4.6 g under ice-cooling, and the mixtures were stirred for
three hours under ice-cooling. To the resulting reaction
mixtures was added saturated aqueous sodium thiosulfate
solution, and the mixtures were extracted with chloroform.
The resulting organic layers were washed successively with
15 saturated aqueous sodium hydrocarbonate solution and
saturated brine, dried over anhydrous sodium sulfate, and
concentrated under reduced pressure. The resulting
residues were subjected to a silica gel column
chromatography to give an intermediate compound 3
20 represented by the following formula 2.8g.
O_ /-CH3 I S -N
- O \ _ CF3 NX
Intermediate compound 3
'H-NMR (CDCl3 ) 6: 8.45 (1H, d), 8.29 (lH, d), 8.28 (1H, d), 190
7.98 (1H, dd), 7.64 (1H, d), 7.51-7.38 (5H, m), 5.45 (2H,
s), 3.55 (2H, q), 1.32 (3H, t). [02021 Preparation example 4
5 The mixture of the intermediate compound 3 2.8 g,
boron tribromide (2M dichloromethane solution) 11 mL, and
chloroform 60 mL was stirred for 2 hours under ice-cooling.
To the resulting reaction mixtures was added water, and the
mixtures were extracted with chloroform. The resulting
10 organic layers were washed successively with saturated
aqueous sodium hydrocarbon solution and saturated brine,
dried over anhydrous sodium sulfate, and concentrated under
reduced pressure. The resulting residues were subjected to
a silica gel column chromatography to give an intermediate
15 compound c-16 represented by the following formula 20 g.
O, /-CH3 S _N0 HO \/ CF 3 N
Intermediate compound c-16
'H-NMR (DMSO-D 6 ) 5: 8.24 (1H, s), 8.21 (1H, d), 8.09 (1H,
d), 7.88 (1H, d), 7.86 (1H, br s), 3.67 (2H, q), 1.17 (3H,
20 t). [0203] Preparation example 5
The mixture of the intermediate compound c-16 300 mg,
/ n 1 /I 1 1 \ .nI I 191
cesium carbonate 350 mg, 2,2,2
trifluoroethyl=trifluoromethanesulfonate 230 mg, and NMP 4
mL was stirred at room temperature for 2.5 hours. To the
resulting reaction mixtures was added water, and the
5 mixtures were extracted with ethyl acetate. The resulting
organic layers were washed with saturated brine, dried over
anhydrous sodium sulfate, and concentrated under reduced
pressure. The resulting residues were subjected to a
silica gel column chromatography to give the Present
10 compound 1 represented by the following formula 220 mg and
the side product 1 100 mg.
[0204)
The Present compounds that are prepared according to
the Preparation example 5 and their physical properties are
15 shown below.
A compound represented by formula (I-1)
/-CH3 (O).S
N R'-O Ni R3b )
wherein Al, Ri, Rb,3 and n are indicated in Table 6.
[0205]
20 Table 6
[Table 63
Present A' R' R n compound 1 CH CF 3CH 2 CF3 2 192
|2 C CF2HCF2CH 2 CF3 2 3 |CH CF3CFHCF2CH 2 CF 3 2 Present compound 1
'H-NMR (CDC13 ) 5: 8.45 (1H, d), 8.38 (1H, d), 8.27 (1H, d),
8.01-7.98 (1H, m), 7.63 (1H, d), 4.83 (2H, q), 3.52 (2H, q),
1.32 (3H, t).
5 Present compound 2
1H-NMR (CDC>) 5: 8.45 (1H, s), 8.35 (1H, t), 8.28 (1H, t),
7.99 (1H, dd), 7.63 (1H, d), 6.18-5.89 (1H, m), 4.82 (2H,
td), 3.52 (2H, q), 1.32 (3H, t).
Present compound 3
10 IH-NMR (CDC13 ) 5: 8.45 (1H, d), 8.36 (1H, d), 8.29 (1H, d),
8.00 (1H, dd), 7.63 (1H, d), 5.26-504 (1H, m), 4.87-4.76
(2H, m), 3.52 (2H, q), 1.33 (3H, t).
[0206]
The side products that are prepared according to
15 Preparation example 5 and their physical properties are
shown below.
A compound represented by formula (B-1)
p-CH 3 (O)IS -N O N R 3b (B-1) N A' R1 wherein Al, RRI , and n are indicated in Table 7.
20 [02071
Table 7 193
[Table 7]
Side Ai Ri R,3E n product
1 CH CF3CH 2 CF3 2 2 CH CF2HCF2CH CF3 2 3 CH CF3CFHCF7CH2, CF3 2 Side product I
'H-NMR (CDC1) 5: 8.43 (IH, s), 8.25 (1H, d), 7.97 (1H, dd),
7.63 (1H, d), 7.42 (iH, s), 4.62 (2H, q), 3.41 (2H, q),
5 1.30 (3H, t).
Side product 2
'H-NMR (CDCl3 ) 6: 8.43 (1H, d), 8.24 (lH, d), 7.96 (1H, dd),
7.63 (1H, d), 7.43 (1H, d), 5.96 (1H, tt), 4.58 (2H, t),
3.42 (2H, q), 1.30 (3H, t).
10 Side product 3
'H-NMR (CDCl3 ) 6: 8.43 (1H, d), 8.25 (iH, d), 7.96 (1H, dd),
7.63 (1H, d), 7.43 (lH, d), 5.17-4.95 (lH, m), 4.71-4.49
(2H, m), 3.41 (2H, q), 1.30 (3H, t).
[0208]
15 Preparation example 6(1)
The mixture of methyl 5-chloro-2-pyridine carboxylate
10 g, sodium methoxide (28 % methanol solution) 28 mL, and
THF 100 mL was stirred for 3 hours under ice-cooling. To
the resulting reaction mixtures was added ethyl methyl
20 sulfone 18 mL under ice-cooling. The reaction mixtures
were raised to 80°C, and heated with stirring for 24 hours.
The resulting reaction mixtures were allowed to cool to 194
room temperature and to the mixtures was added 2N
hydrochloric acid and the mixtures were extracted with
ethyl acetate. The resulting organic layers were dried
over anhydrous sodium sulfate and concentrated. The
5 resulting residues were subjected to a silica gel column
chromatography to give the intermediate compound e-18
represented by the following formula 11 g.
O" /CH3 0 S -N
H 3C N 0
'H-NMR (CDCl3 ) 5: 8.91 (1H, d), 8.25 (1H, d), 4.87 (2H, s),
10 4.08 (3H, s), 3.29 (2H, q), 1.47 (3H, t).
[0209]
Preparation example 6(2)
The mixture of the intermediate compound e-18 5.0 g,
ammonium acetate 7.89 g, and methanol 15.0 g was heated at
15 700C with stirring for 4 hours. The reaction mixtures were
concentrated under reduced pressure to obtain the crude
product 12.9 g, and thereto was added ethyl acetate 25 g to
dissolve it. The mixtures were washed with water 15 g
three times. The resulting organic layers were
20 concentrated under reduced pressure to give the
intermediate compound 18 represented by the following
formula 4.5 g.
/ n n 1 /I 1 1 \ .nI I 195
0, /-CH 3
H 3C N NH2 Intermediate compound 18
1H-NMR (CDC13) 5: 8.52 (1H, d), 8.21 (1H, d), 6.69 (2H, br),
5.31 (1H, s), 4..03 (3H, s), 3.11 (2H, q), 1.41 (3H, t)
5 [0210]
Preparation example 7
To a mixture of DMF 19 mL and chloroform 600 mL was
added oxalyl chloride 21 mL under ice-cooling. The
reaction mixtures were raised to room temperature, and
10 stirred for 2 hours. To the resulting reaction mixtures
was added butyl vinyl ether 64 mL under ice-cooling and the
mixtures were stirred for 3 hours. To the resulting
reaction mixtures were added the intermediate compound e-18
20 g and triethylamine 68 mL. The reaction mixtures were
15 stirred for 6 hours, and then concentrated under reduced
pressure. To the resulting residues were added ethanol 300
mL and 28 % aqueous ammonia solution 30 mL. The reaction
mixtures were heated with stirring at 60°C for 12 hours.
The reaction mixtures were concentrated under reduced
20 pressure. To the resulting residues was added water, and
the mixtures were extracted with ethyl acetate. The
resulting organic layers were dried over anhydrous sodium
sulfate, and concentrated under reduced pressure. The 196
resulting residues were subjected to a silica gel column
chromatography to give the intermediate compound 6
represented by the following formula 11.4 g.
O /-CH3 0 -N .' 0P\./ i\/ H 3C N N
5 Intermediate compound 6
'H-NMR (CDCl 3 ) 5: 8.74 (1H, dd), 8.66 (1H, dd), 8.49 (1H,
d), 8.20 (1H, d), 7.55 (1H, dd), 4.05 (3H, s), 3.85 (2H, q),
1.38 (3H, t).
[0211]
10 Preparation example 8
The mixture of the intermediate compound 6 4.5 g, and
12N hydrochloric acid 20 mL was heated at 1000C with
stirring for 1 hour. The reaction mixtures were allowed to
cool to room temperature, and thereto was added ice water
15 100 mL. The solution was alkalified with saturated aqueous
sodium hydrocarbon solution, and the mixtures were
extracted with ethyl acetate. The resulting organic layers
were dried over anhydrous sodium sulfate, and concentrated
under reduced pressure. The resulting residues were
20 subjected to a silica gel column chromatography to give the
intermediate compound c-2 represented by the following
formula 4.3 g.
[0212]
/ n n 1 /I 1 1 \ .nI I 197
The compounds that prepared according to the method
described in Preparation example 8 and their physical
properties are shown below.
A compound represented by formula (M-3-1)
/-CH3 (O)nS
N -_ HO N- R 3b (M-3-1) 5 N A' wherein A', R3b, and n are indicated in Table 8.
[0213]
Table 8
[Table 8]
Intermediate A' R3 b n compound c-2 N H 2 11 N H 0 10 Intermediate compound c-2
'H-NMR (CDCl3 ) 5: 8.81 (1H, dd), 8.47 (1H, dd), 8.21(1H, d),
7.97 (1H, d), 7.52 (1H, dd), 3.83 (2H, q), 1.39 (3H, t).
Intermediate compound 11
'H-NMR (CDCl3 ) 5: 8.40 (1H, dd), 8.34 (1H, d), 8.04 (1H, br
15 s), 7.69 (1H, dd), 7.24 (1H, dd), 2.94 (2H, q), 1.34 (3H,
t).
[0214]
Preparation example 9
The mixture of the intermediate compound c-2 4.3 g,
20 phosphorus oxychloride 12 mL, and toluene 60 mL was heated
at 1000C with stirring for 2 hours. The resulting reaction
/ n n 1 /I 1 1 \ .nI I 198
mixtures were allowed to cool to room temperature, and
concentrated under reduced pressure. To the resulting
residues was added water, and the mixtures were extracted
with chloroform. The resulting organic layers were dried
5 over anhydrous sodium sulfate and concentrated under
reduced pressure to give the intermediate compound d-2
represented by the following formula 4.6 g.
[0215]
The compounds that prepared according to the method
10 described in Preparation example 9 and their physical
properties are shown below.
A compound represented by formula (M-4-1)
-- CH3 (O)IS N V / X R3b (M-4-1) N- A' 3b wherein V, A', R and n are indicated in Table 9.
15 [0216}
Table 9
[Table 9] Intermediate V A R3 n compound d-2 Cl N H 2 12 [Cl N H 0 13 [Br N H 2 Intermediate compound d-2
'H-NMR (CDCl3) 5: 8.94 (1H, dd), 8.90(lH, dd), 8.59 (1H, d),
20 8.52 (1H, d), 7.65 (1H, dd), 3.81 (2H, q), 1.39 (3H, t). 199
Intermediate compound 12
'H-NMR (CDCI3 ) 5: 9.10 (1H, d), 8.68 (lH, d), 8.49 (lH, dd),
7.75 (1H, dd), 7.33 (1H, dd), 2.94 (2H, q), 1.33 (3H, t).
Intermediate compound 13
5 'H-NMR (CDCl 3 ) 5: 8.91(1H, d), 8.87 (1H, s), 8.67 (1H, s),
8.50(1H, d), 7.62(1H, q), 3.78 (2H, q), 1.37 (3H, t)
[0217]
Preparation example 10
The mixture of the intermediate compound d-2 300 mg,
10 cesium carbonate 480 mg, 2,2,3,3-tetrafluoropropanol 210 mg,
and NMP 4 mL was heated at 70°C with stirring for 2 hours.
The resulting reaction mixtures were allowed to cool to
room temperature, and thereto was added water, and the
mixtures were extracted with ethyl acetate. The resulting
15 organic layers were washed successively with saturated
brine, dried over anhydrous sodium sulfate and concentrated.
The resulting residues were subjected to a silica gel
column chromatography to give the Present compound 4
represented by the following formula 300 mg.
20 [0218]
The compounds that prepared according to the method
described in Preparation example 10 and their physical
properties are shown below.
A compound represented by formula (I-1) 200
r-CHa (O)nS N R'-OfJ- / z R/ R3b (1) N- A' wherein A', R', R 3b and n are indicated in Table 10.
[0219]
Table 10
[ITable 10] Present AR' 7 n compound ______4 N CF2HCECH2 H 2 5 N CF3CF 2CH2 H 2 6 N CF3CFHCF',CH2 - H 2 7 NF H 2
8 NCP 3CH 2 H 2 9 NCF 2HCH2 H 2 10 N CH3CF2CH2 H 2 11 N CF2CH (CH, ) H -2 12 N CP2CP,-CH (CH3) H 2 13 N CPCF2CF,CH2 H 2 14 N CF3 H 2
15N CPICF2CV2CFCH2 H 2 16 N CPBCFUCF2CH (CH3) H 2 17 N F H 2
18 N CC13CHE H 2 19 N CFQCH=CHCH?, H 2 20 N CF3SCH2CH2 H 2 21 N CF3OCH2CH2 H 2 22 N CF3CC12 CH, H 2 23 N CF3C-=CCH2 H 2 24 jN F3C H 12 25 IN CF3CH=CECH2 H 2 26 JN CF3CECH2 }CF3 2 27 N CF2HCFCH2 CF3 12 201
28 N CF 3 CFHCF2CH 2 CF3 2
29 N CF 3 CF2 CF2 CH2 CF3 2
30 N CF 3 CH (CH3 ) CF3 2
31 N CF 3 CF2 CH (CH3 ) CF3 2
32 N CF 3 CF2 CF2 CH (CH3 ) CF3 2 [0220]
Present compound 4
'H-NMR (CDCl 3 ) 5: 8.90 (1H, dd), 8.66 (1H, d), 8.50 (1H,
dd), 8.31 (1H, d), 7.59 (1H, dd), 6.03 (1H, tt), 4.83 (2H,
5 tt), 3.83 (2H, q), 1.38 (3H, t).
Present compound 5
'H-NMR (CDCl 3 ) 5: 8.90 (1H, dd), 8.66 (1H, d), 8.50 (1H,
dd), 8.33 (1H, d), 7.59 (1H, dd), 4.91 (2H, td), 3.83 (2H,
q), 1.38 (3H, t).
10 Present compound 6
'H-NMR (CDCl 3 ) 5: 8.91 (1H, dd), 8.67 (1H, d), 8.50 (1H,
dd), 8.32 (1H, d), 7.59 (1H, dd), 5.27-5.03 (1H, m), 4.89
4.78 (2H, m), 3.83 (2H, q), 1.39 (3H, t).
Present compound 7
15 'H-NMR (CDCl3 ) 5: 8.91-8.88 (1H, m), 8.63 (1H, d), 8.49 (1H,
dd), 8.22 (1H, d), 7.56 (1H, dd), 4.59-4.39 (2H, m), 3.85
(2H, q), 2.25-2.12 (1H, m), 1.41-1.29 (5H, m).
Present compound 8
'H-NMR (CDCl3 ) 5: 8.89 (1H, d), 8.64 (1H, s), 8.49 (1H, d),
20 8.32 (1H,s), 7.57 (1H, dd), 4.83 (2H, q), 3.82 (2H, q),
1.37 (3H, t),
Present compound 9
/ n n 1 /I 1 1 \ .nI I 202
'H-NMR (CDCl 3 ) 5: 8.89 (1H, d), 8.63 (1H, s), 8.48 (1H, d),
8.28 (1H, s), 7.56 (1H, dd), 6.16 (1H, tt), 4.62 (2H, td),
3.82 (2H, q), 1.37 (3H, t)
Present compound 10
5 1H-NMR (CDCl 3 ) 5: 8.89 (1H, d), 8.63(1H, s), 8.48 (1H, d),
8.28 (1H, s), 7.54-7.58 (1H, m), 4.58 (2H, t), 3.83 (2H, q),
1.77 (3H, t), 1.37 (3H, t)
Present compound 11
'H-NMR (CDCl 3 ) 5: 8.90 (1H, dd), 8.64 (1H, d), 8.50 (1H,
10 dd), 8.27 (1H, d), 7.58 (1H, dd), 5.84-5.74 (1H, m), 3.84
(2H, m), 1.56 (3H, d), 1.39 (3H, t).
Present compound 12
'H-NMR (CDCl 3 ) 5: 8.90 (1H, dd), 8.65 (1H, d), 8.51 (1H,
dd), 8.26 (1H, d), 7.58 (1H, dd), 5.90 (1H, dq), 3.85 (2H,
15 m), 1.58 (3H, d), 1.39 (3H, t).
Present compound 13
'H-NMR (CDCl 3 ) 5: 8.88 (1H, dd), 8.64 (1H, d), 8.48 (1H,
dd), 8.31 (1H, d), 7.57 (1H, dd), 4.93 (2H, t), 3.81 (2H,
q), 1.36 (3H, t).
20 Present compound 14
'H-NMR (CDCl 3 ) 5: 8.89 (1H, dd), 8.61 (1H, d), 8.50 (1H,
dd), 8.28 (1H, d), 7.57 (1H, dd), 5.28 (1H, m), 3.92-3.79
(2H, m), 1.39 (3H, t), 1.34-1.28 (1H, m), 0.82-0.62 (4H, m).
Present compound 15
25 'H-NMR (CDCl3 ) 5: 1.38 (3H, q), 3.82 (2H, q), 4.96 (2H, t),
/ n n 1 /I 1 1 \ .nI I 203
7.57 (1H, dd), 8.32 (1H, s), 8.49 (1H, d), 8.65 (1H, s),
8.89 (1H, d)
Present compound 16
'H-NMR (CDCl3 ) 5: 1.37 (3H, m), 1.54 (3H, m), 3.80-3.88 (2H,
5 m), 5.88-6.00 (1H, m), 7.57 (1H, dd), 8.24 (1H, s), 8.50
(1H, d), 8.65 (1H, s), 8.88 (1H, d)
Present compound 18
'H-NMR (CDCl3 ) 5: 1.38 (3H, t), 3.83 (2H, q), 5.11 (2H, s),
7.53-7.63 (1H, m), 8.37 (1H, s), 8.49 (1H, d), 8.65 (1H, s),
10 8.89 (1H, d)
Present compound 19
'H-NMR (CDCl3 ) 5: 1.38 (3H, t), 3.06-3.18 (2H, m), 3.82 (2H,
d), 4.99-5.09 (1H, m), 7.53-7.66 (2H, m), 8.32 (1H, s),
8.49 (1H, d), 8.65 (1H, d), 8.89 (1H, s)
15 Present compound 24
'H-NMR (CDCl3 ) 5 0.92 (2H, s), 1.18 (2H, s), 1.36 (3H, t),
3.82 (2H, q), 4.51 (2H, s), 7.53-7.56 (1H, m), 8.22 (1H, s),
8.47 (1H, d), 8.60 (1H, s), 8.87 (1H, d)
[0221]
20 Preparation example 11
The mixture of 2-bromo-5-methoxypyradine 4.9 g, (3
fluoropyridin-2-yl)tributyltin 14 g,
tetrakis(triphenylphosphine)palladium(0) 0.60 g, and
copper(I) iodide 1.0 g, lithium chloride 1.7 g, and toluene
25 60 mL was heated under reflux with stirring for 10 hours.
/ n n 1 /I 1 1 \ .nI I 204
The resulting reaction mixtures were allowed to cool to
room temperature, and thereto was added water, and the
mixtures were extracted with ethyl acetate. The resulting
organic layers were washed with saturated brine, dried over
5 anhydrous sodium sulfate, and concentrated. The resulting
residues were subjected to a silica gel column
chromatography to give the intermediate compound 9
represented by the following formula 5.2 g.
F -N 0 / "' / H 3 C N N
10 Intermediate compound 9
'H-NMR (CDCl3 ) 5: 8.80 (1H, s), 8.61-8.58 (1H, m), 8.41 (1H,
d), 7.59-7.53 (1H, m), 7.39-7.33 (1H, m), 4.05 (3H, s).
[02221
Preparation example 12
15 To the mixture of the intermediate compound 9 5.2 g,
sodium hydride (60 %, oily), and DMF 85 mL was added
ethanethiol 1.7 g under ice-cooling. The resulting
mixtures were stirred at room temperature for 3 hours. To
the resulting reaction mixtures was added water, and the
20 mixtures were extracted with ethyl acetate. The resulting
organic layers were washed with saturated brine, dried over
anhydrous sodium sulfate, and concentrated. The resulting
residues were subjected to a silica gel column
/ n n 1 /I 1 1 \ .nI I 205
chromatography to give the intermediate compound 10
represented by the following formula 4.4 g.
CH 3 S
-N
H 3C N N
Intermediate compound 10
5 'H-NMR (CDCla) 6: 8.75 (1H, d), 8.46 (1H, dd), 8.32 (1H, d),
7.71 (lH, dd), 7.27 (1H, dd), 4.04 (3H, s), 2.92 (2H, q),
1.31 (3H, t).
[02231
Preparation example 13
10 The mixture of the intermediate compound 12 2.9 g,
mCPBA (75 %) 5.6 g, and chloroform 40 mL was stirred under
ice-cooling for 4 hours. To the resulting reaction
mixtures was added saturated aqueous sodium thiosulfate
solution, and the mixtures were extracted with chloroform.
15 The resulting organic layers were washed successively with
saturated aqueous sodium hydrocarbon solution, water, and
saturated brine, dried over anhydrous sodium sulfate, and
concentrated under reduced pressure. The resulting
residues were subjected to a silica gel column
20 chromatography to give the intermediate compound d-2 2.8 g.
[02241
Preparation example 14-1
To the mixture of magnesium chloride 5.16 g, 206
triethylamine 9.15 g and THF 24 g was added 1
ethanesulfonyl-2-propanone 8.15 g at room temperature and
the mixtures were stirred for 1 hour. To the mixtures was
added dropwise a mixture of 5-chloro-2-pyradine carboxylic
5 acid chloride 8.0 g and ThF 8 g over 30 minutes, and the
mixtures were stirred at room temperature for 3 hours. To
the mixtures was added 13 % hydrochloric acid 25 g, and the
mixtures were stirred for another 17 hours. The resulting
mixtures were extracted with toluene 40 g, and the organic
10 layers were washed with water twice (water 16 g, water 8 g,
successively). The resulting organic layers were
concentrated under reduced pressure. The resulting
residues were recrystallized from toluene 8 g to give the
intermediate compound e-16 represented by the following
15 formula 9.16 g.
O,/-CH 3 /S 0 N N 0
Intermediate compound e-16
H-NMR (CDC13 ) 5: 9.08 (1H, d), 8.70 (1H, d), 4.89 (2H, s),
3.29 (2H, q), 1.48 (3H, t)
20 £0225]
Preparation example 14-2
The compounds that prepared according to the method
described in Preparation example 14-1 and their physical 207
properties are shown below.
, /-CH3 !F N
F O
Intermediate compound e-24
'H-NMR (CDCl 3 ) 5: 8.90 (1H, d), 8.40 (1H, d), 4.95 (2H, td),
5 4.88 (2H, s), 3.29 (2H, q), 1.47 (3H, t).
[0226]
Preparation example 15-1
The mixture of the intermediate compound e-16 2.2 g,
ammonium acetate 3.4 g and methanol 10 g was stirred at
10 700C for 3 hours. The mixtures were cooled to room
temperature, and thereto was added water, and the mixtures
were extracted with ethyl acetate. The resulting organic
layers were washed with water 10 g, dried over anhydrous
sodium sulfate, and concentrated under reduced pressure to
15 give the intermediate compound f-16 represented by the
following formula 1.6 g.
O/-CH3 ,S
CI N- NH 2 Intermediate compound f-16
'H-NMR (DMSO-d6) 5: 9.05 (1H, d), 8.89 (1H, d), 7.01 (2H,
20 br), 5.67 (1H, s), 3.09 (2H, q), 1.23 (3H, t)
[0227] 208
The compounds that prepared according to the method
described in Preparation example 15-1 and their physical
properties are shown below.
FF O0 /-CH3 F S FFO
N NH 2
5 iH-NMR (CDCl 3 ) 5: 8.52 (1H, d), 8.35 (1H, d), 6.68 (1H, s),
5.34 (1H, s), 4.91 (2H, td), 3.11 (2H, q), 1.41 (3H, t).
[0228)
Preparation example 16(1)
To the mixtures of the intermediate compound f-16 1.0
10 g, acetic acid 0.27 g, and methanol 3.0 g was added
acrolein 0.27 g at 60°C, and the mixtures were stirred for
5 hours. To the mixtures was added acrolein 0.045 g, and
the mixtures were stirred for another 3 hours. The
mixtures were concentrated under reduced pressure to give
15 the intermediate compound 16 represented by the following
formula 1.3 g.
(02-CH3 (O)2S N CI1 N~ HN
O-CH 3
Intermediate compound 16
'H-NMR (CDCl3 ) 5: 8.54 (2H, m), 5.12 (1H, s), 4.60 (1H, q),
20 3.41 (3H, s), 2.95 (2H, m), 2.67(1H, m), 2.53 (1H, m), 2.22 209
(1H, m), 1.77 (1H, m), 1.24 (3H, t)
[0229]
Preparation example 16(2)
The intermediate compound 19 represented by the
5 following formula was obtained by using the intermediate
compound 18 instead of the intermediate compound f-16
according to the method described in Preparation example
16(1).
0 /-CH3
/Z O O -N H3C N~ HN O-CH 3
10 Intermediate compound 19
'H-NMR (CDCl) 5: 8.31 (1H, d), 8.15 (1H, d), 5.21 (1H, br),
4.59 (1H, m), 4.00 (3H, s), 3.37 (3H, s), 2.94 (2H, m),
2.67 (1H, m), 2.52 (1H, m), 2.19 (1H, m), 1.75 (1H, m),
1.22 (3H, t)
15 [0230]
Preparation example 17
The intermediate compound 16 0.10 g, vinyl acetate
0.16 g and acetic acid 1.0 g and 5% Pd-C 0.010 g were mixed,
and the reaction vessel was replaced with nitrogen gas, and
20 the mixtures were heated at 60°C with stirring for 3 hours,
and heated at 100°C with stirring for 2 hours. The
resulting reaction mixtures were analyzed by a high 210
performance liquid chromatography and confirmed that
contained 21 % area percentage of the intermediate compound
d-2.
(0231]
5 Preparation example 18
To the mixtures of the intermediate compound e-16 50 g,
triethylamine 0.41 g, methanol 12.5 g, and toluene 12.5 g
was added acrolein 1.35 g at room temperature, and the
mixtures were stirred for 1 hour. It was confirmed by 'H
10 MAR that the mixtures contained the intermediate compound
17.
o, O-CH 3
NO
N-- 0 OH
Intermediate compound 17
'H-NMR (CDCl3 ) 6: 9.73 (1H, s), 9.08 (1H, d), 8.66 (1H, d),
15 5.83 (1H, dd), 3.17 (2H, m), 2.60 (2H, m), 2.50 (2H, m),
1.41 (3H, t)
Without isolating the intermediate compound 17, to the
resulting reaction mixtures was added ammonium acetate 1.86
g, and the mixtures were stirred at room temperature for 7
20 hours. To the resulting reaction mixtures were added water
10 g, and the mixtures were extracted with ethyl acetate
250 g. The resulting organic layers were washed with water 211
10 g, and concentrated under reduced pressure to give the
intermediate compound 16 6.0 g.
[0232]
Preparation example 19
5 The mixture of the intermediate compound 19 50 g, THF
10.0 g and methanesulfonyl chloride 0.50 g was stirred at
60°C for 3 hours. The resulting reaction mixtures were
analyzed by a high performance liquid chromatography and
confirmed that the mixtures contained 29% area percentage
10 of the intermediate compound 6.
[0233]
Preparation example 20
The mixtures of the intermediate compound 20 20 g,
2,2,3,3,3-hexafluoropropanol 0.61 mL, cesium carbonate 20 g
15 and DMF 20 mL was stirred at 400C for 3 hours. The
reaction mixtures were added to IN hydrochloric acid and
the mixtures were extracted with ethyl acetate. The
resulting organic layeres were dried over anhydrous sodium
sulfate, and concentrated under reduced pressure. The
20 resulting residues were subjected to a silica gel column
chromatography to give the Present compound 343 1.9 g as a
crude product.
0, /CH3
ClN) Os Cl-!' - \ /\ "N N 212
Intermediate compound 20
1 H-NMR (CDCl 3 ) 5: 8.84 (1H, d), 8.63 (lH, d), 8.55 (1H, d),
8.03 (1H, d), 7.48-7.30 (SH, m), 5.27 (2H, s), 3.84-3.77
(2H, m), 1.32 (3H, t).
F F O /CH3
F N F D 0\ 0 5 N N O
Present compound 343
'H-NMR (CDCl 3 ) 5: 8.61 (lH, d), 8.58 (lH, d), 8.30 (1H, d),
8.03 (1H, d), 7.48-7.36 (5H, m), 5.26 (2H, s), 4.89 (2H,
td), 3.80 (2H, q), 1.31 (3H, t).
10 [0234]
Preparation example 21
The mixtures of the Present compound 343 1.9 g as
crude product, and HBr in acetic acid 4 mL was stirred at
70°C for 2 hours. To the reaction mixtures was added water,
15 and the mixtures were extracted with ethyl acetate. The
resulting organic layeres were dried over anhydrous sodium
sulfate, and concentrated under reduced pressure. The
resulting residues were subjected to a silica gel column
chromatography to give the Present compound 344 1.0 g.
F OF /-CH3 F F N F O ~ OH 20 N N
Present compound 344 213
'H-NMR (CDCT 3 ) 5: 8.59 (1H, d), 8.53 (1H, d), 8.30 (1I, d),
7.99 (1H, d), 4.90 (2H, dd), 3.85 (2H, q), 1.39 (3H, t).
[0235]
Preparation example 22
5 The mixture of the Present compound 344 0.33 g,
isopropyl iodide 0.12 mL, cesium carbonate 390 mg, and DMF
2 mL was stirred at room temperature for 1 hour. To the
reaction mixtures was added water, and the mixtures were
extracted with MTBE. The resulting organic layers were
10 dried over anhydrous sodium sulfate, and concentrated under
reduced pressure. The resulting residues were subjected to
a silica gel column chromatography to give the Present
compound 279 0.26 g.
F F O, /-CHs
F ONO
15 Present compound 279
'H-NMR (CDC13) 5: 8.57 (1H, d), 8.51 (IH, d), 8.30 (1H, d),
7.93 (IH, d), 4.89 (2H, t), 4.78-4.72 (1H, m), 3.82 (2H, q),
1.43 (6H, d), 1.38 (3H, t).
[0236]
20 Preparation example 23
The compounds that prepared according to the method
described in Preparation example 22 and their physical
properties are show below. 214
F FO /-CH3 F 12 S F N FF O Of-CH3 =N N
Present compound 274
1 H-NMR (CDC13 ) 5: 8.58 (1H, d), 8.55 (1H, d), 8.30 (1H, d),
7.94 (1H, d), 4.90 (2H, t), 4.23 (2H, q), 3.82 (2H, q),
5 1.51 (3H, t), 1.38 (3H, t).
F F F CS CH3
F 0 \O
Present compound 339
'H-NMR (CDC13 ) 5: 8.57 (1H, d), 8.55 (1H, d), 8.30 (1H, d),
7.94 (1H, d), 4.89 (2H, t), 4.11 (2H, t), 3.82 (2H, q),
10 1.92-1.88 (2H, m), 1.38 (3H, t), 1.10 (3H, t).
F O, /-C H3 F OrCCH3
_N
Present compound 340
'H-NMR (CDC13) 5: 8.58 (1H, d), 8.55 (1H, d), 8.28 (1H, d),
7.94 (1H, d), 6.02 (1H, tt), 4.81 (2H, tt), 4.11 (2H, t),
15 3.82 (2H, q), 1.90 (2H, td), 1.38 (3H, t), 1.09 (3H, t).
F O O N
Present compound 280 215
H-NMR (CDCl 3 ) 6: 8.58 (1H, d), 8.51 (lH, d), 8.28 (1H, d),
7.93 (1H, d), 6.02 (lH, tt), 4.85-4.70 (3H, m) , 3.82 (2H,
q), 1.43 (6H, d), 1.38 (3H, t).
[0237]
5 Preparation example 24
The mixture of the Present compound 345 1.4 g, N
bromosuccinimide 680 mg, and acetic acid 7 mL was heated
under reflux with stirring for 24 hours. The resulting
mixtures were made pH 11 with 1N sodium hydroxide. To the
10 mixtures was added saturated aqueous sodium sulfite
solution, and the precipitated solids were filtered and
washed with water to give the Present compound 346 860 mg.
F F o -CH3 F
F F NO FN N~9 OH Present compound 345
15 'H-NMR (CDCl3 ) 6: 8.52 (1H, d), 8.40 (1H, d), 8.01 (1H, d),
6.63 (1H, d), 4.93 (2H, t), 3.39 (2H, q), 1.31 (3H, t).
F F , -CH3 F ONs F o-Br N N~ OH Present compound 346
'H-NMR (CDCl 3 ) 5: 8.63 (1H, s), 8.42 (1H, s), 8.38 (1H, s),
20 4.93 (2H, t), 3.36-3.27 (2H, m), 1.32 (3H, t).
[0238] 216
Preparation example 25
The mixtures of the Present compound 346 860 mg, 4
fluorophenyl boronic acid 270 mg,
tetrakis(triphenylphosphine)palladium(0) 32 Mg, 2
5 dicyclohexylphosphino-2'-6'-dimethoxybiphenyl 57 Mg,
tripotassium phosphate 1.5 g, and dimethoxyethane 4.5 mL
and was heated under reflux with stirring for 10 hours. To
the resulting mixtures was added water, and the mixtures
were extracted with ethyl acetate. The resulting organic
10 layers were dried over anhydrous sodium sulfate, and
concentrated under reduced pressure. The resulting residues
were subjected to a silica gel column chromatography to
give the Present compound 347 280 mg.
F FI O, /-CH3 F N F SFO F =N N~~ OH 15 Present compound 347
'H-NMR (DMSO-D ) 5: 8.64 (1H, d), 8.60 (1H, d), 7.95 (1H,
s), 7.85 (2H, dd), 7.33-7.-28 (2H, m), 5.27 (2H, t), 3.50
3.39 (2H, m), 1.23-1.15 (3H, m).
[02391
20 Preparation example 26
The mixtures of the Present compound 347 280 mg, and
phosphorus oxychloride 5 mL was heated under reflux with
stirring for 72 hours. The resulting reaction mixtures 217
were concentrated under reduced pressure. To the resulting
residues were added saturated aqueous sodium hydrocarbon
solution under ice-cooling and the mixtures were extracted
with ethyl acetate. The resulting organic layers were
5 dried over anhydrous sodium sulfate, and concentrated under
reduced pressure. The resulting residues were subjected to
a silica gel column chromatography to give the Present
compound 348 130 mg.
F O0 /-CH3 F F F F O F _ _N N~ C1 10 Present compound 348
'H-NMR (CDCl3) 5: 8.75 (1H, d), 8.43 (1H, s), 8.35 (1H, d),
7.57-7.51 (2H, m), 7.26-7.19 (2H, m), 4.93 (2H, t), 3.89
(2H, q), 1.42 (3H, t).
[0240]
15 Preparation example 27
The mixtures of the intermediate compound e-24 390 mg,
the intermediate compound 21 200 mg, sodium hydride (60%,
oily) 95 mg, and THF 5 mL was stirred under ice-cooling for
24 hours. To the resulting reaction mixtures were added
20 ammonium acetate 830 mg and ethanol 5 mL under ice-cooling.
The resulting reaction mixtures were stirred at 80°C for 24
hours. The resulting reaction mixtures were concentrated
under reduced pressure, and the resulting residues were 218
subjected to a silica gel column chromatography to give the
Present compound 194 120 mg.
F F or-CH3 F OIF FF o.-4 j\= / \ F
Present compound 194
5 H-NMR (CDCl 3 ) 6: 9.07 (1H, d), 8.71 (1H, d), 8.63 (1H, d),
8.35 (1H, d), 7.69-7.66 (2H, m), 7.28-7.25 (2H, m), 4.92
(2H, td), 3.89 (2H, q), 1.45-1.40 (3H, m).
[0241]
The compounds represented by formula (100)
,r-CH 3 60 301 R 1 (O) 2S R N R 100 0 R 302 (100) N- -A- A -~ 10 R602 R303
[wherein, R30 , R'02, R 03, RE0i, Rso 2 , R'0', and A' represent
any one of the combination indicated in the following Table
11 to Table 36]
can be prepared according to the processes described above.
15 [0242]
Table 11
[Table 11]
Prese A R k R0 R3T7 R601 R 62 nt compo und L3 N CF2HCH2 H H NH2 H H 219
34 N CF3CF2CH2 H H NH 2 H H 35 N CF2HCF2CH 2 H H NH2 H H 36 N CF3CF2CF2CH H H NH2 H H 2 37 N CF3CFHCF2CH H H NH 2 H H 2 38 N CF 2HCH 2 H H NHCH 3 H H 39 N CP2CP2 OCH2 H H NHCH 3 H H 40 N CF 2HCF 2CH 2 H H NHCH3 H H 41 N CF3CF2 CF2CH H H NHCH 3 H H 2 42 N CF3CFHCF2CH H H NHCH 3 H H 2
43 N CF2HCH 2 H H N (CH 3 ) 2 H H 44 N CF3 CF2CH2 H H N (CH 3 ) 2 H H 45 N CF2 HCF2CH2 H H N(CH 3 ) 2 H H
46 N CF3CF2CF2CH H H N(CH 3 ) 2 H H
47 N CF3CFHCF2CH H H N(CH 3 ) 2 H H 2 HC2 N(C2H3_ 48 N CF2HCH 2 H H N(CH 2CH 3 ) H H 50 N CF2HCF2CH2____ H H (C2CH 2 49 N CF 3CF2CH2 H H N(CH 2CH3 ) H H 2 _ 2 50 N CF2HCF2 CH2 H H N (CH 2CH 3) H H
51 N CF3CP2C 2 CH H H N(CH 2CH 3) H H
_ _ 2 2 22_ __ _ 52 N CF3CFHCP2CH H H N(CH 2CH 3) H H
53 N OF>)HCH2, H H NHCH2CF3 H H 54 N CF3CF2CH 2 H H NHCH 2OF3 H H 55 N CF 2HCF 2CH2 H H NHCH2CF3 H H 56 N CF3CF2CF2CH H H NHCHPCF3 H H 2 57 N CF 3CFHCF2CH H H NHCH 2CF3 H H 2 [0243]
Table 12
[Table 12]
R'0 Present A R 3 m Rm R compound
58 N CF2 HCH2 H H C1 H H 220
59 N CF3CF2 CH2 H H Cl H H 60 N CF2HCF2CH 2 H H Cl H H 61 N CF3CCF2 CH 2 H H Cl H H 62 N CF3CFHCF2CH 2 H H Cl H H 63 N CF2 HCH2 H Cl H H H 64 N CF3CF 2CH 2 H Cl H H H 65 N CF2HCF 2CH2 H Cl H H H
66 N CF3CF2 CF 2 CH2 H Cl H H H 67 N CF3CFHCF2CH2 H Cl H H H 68 N CF2HCH 2 H H OCH 3 H H 69 N CF 3CF 2CH 2 H H OCH3 H H 70 N CF2HCF2CH 2 H H OCH 3 H H 71 N CF3CF2CF2CH2 H H OCH 3 H H 72 j N CF3 CFHCF2CH2 H H OCH 3 H H [0244]
Table 13
[Table 13}
6 6 2 Present A-- RR 3 Rm 30 R compound N CF 2HCH, H H -N H H 73 N
N CF3 CF2CH2 H H N H H
N CFYHCF2CH2 H H IN\N H H
75 N 7 N CF3CFHCFCH2 H H N H H
76•,-- N CF3CFHCF2 CHQ H H N NN H H 77N
N CF 2HCH, H H N CI H H 78 N
N CF3CF2 CH 2 H H N
N CF 2 HCF2 CH2 H H N~ CI H H
N CF3CFCFCH? H H N~ C1 H H 81 N'
N CF 3CFHCF2CH2 H H N CI H H 82 --N
[0245] 221
Table 14
[Table 14] Present A R 00 R30 R302 R303 Roi R602 compound;
N CF2HCH 2 H H N OCH 3 H H
\- N _
N CF3 CF2CH2 H H N OCH 3 H H -N
N CF2HCF2 CH2 H H N OCH 3 H H ---N
N CF 3CF2 CF2 CH2 H H N\,N OCH3 H H
86 \-- N N
N CF2HCH2CF3CCF2CH2 H H NzzN OC32NH 2 H H 88,_ \:-N
N CF3 CF2CH2 H H N NH2 H H 89•
N CF2HCFCH, H H N NH 2 H H 90 -- N N _ _ _ _
91 N CF3 CFCF2CH2 H H ~NNNH 2 H H N
N CF3CFHCF2CH7 H H N~ NH2 HH 92 •-NN __
[0246]
Table 15
5 [Table 15)
Present A' R R 3 R R 6° R compound |
N CF2HCH2 H H ,N, S(0)2CH 3 H H
\:N
N CF3CF2CH2 H H ,N S(O)2CH 3 H H \--N
N CF2HCF2CH2 H H N S(0) 2 CH 3 H H 95 -N 222
N CF 3CF 2CF 2CH 2 H H ,N' S(O) 2CH 3 H H 96 ,N\N
N CF 3 CFHCF 2 CH 2 H H Ns S(0) 2 CH3 H H
N CF 2HCH 2 H H N CN H H 98 ,_N \-N
N CF 3 CF 2 CH 2 H H ,N CN H H
\N N CF 2HCF 2CH 2 H H N CN H H 100 ,_N \-,N N CF 3CF 2CF 2CH 2 H H ,N CN H H 101 ,_ \-,N
N CF 3CFHCF 2CH 2 H H N CN H H 102 *-N _N [0247]
Table 16
[Table 16]
Present A' R10 0 R 3 0 1 R 3 0 2 R 3 03 R 6 0 1 R 60 2 compound H H H CF 3 H 103 N CF 2HCH 2 \sN H H H CF 3 H 104 N CF 3CF 2CH 2 N H H H •-N CF 3 H 105 N CF 2HCF 2CH 2 N H H H CF 3 H 106 N CF 3CF 2CF 2CH 2 \sN H H CH H H CF 3 107 N CF 3CFHCF 2 2 \sN
N CF 2HCH 2 H H N CF 3 H H 108 ,_N
N CF 3CF 2CH 2 H H N CF 3 H H 109 ,_N 223
N CF 2HCF2CH2 H H N CF3 H H 110 •-N
N CF3CF2CF2CH2 H H N CF3 H H 111 -NN
N CF H H 112 N CF3CFHCF2CH 2 H H 3
[0248]
Table 17
[Table 17] Present A R 0 R3 R 2R R R compound N CF2HCH 2 H H N-N H H 113 •-N
N CF3CF2CH2 H H IN2N H H 114 ~N
115 N CF2HCF2CH2 H H NN H H
N CF3CF2CF2CH2 H H NzN H H 116 .- N
N CF3CFHCF2CH2 H H NaN H H 117 •-N
N CF2HCH 2 H H N, H H 118• N N CF3CF2CH 2 H H -N H H 119N N N CF2HCF2CH2 H H N H H 120•
N CF3CF2CF2CH2 H H IN H H 121 N N N CF3CFHCF2 CH2 H H N H H 122 N
[0249]
5 Table 18 224
[Table 18] Presen 4 R R R37 R27 Rti R7 corapori
N- H H 13 N CFHCH2 , H ~H 0
N- H H 14 N CP3 CF2 CH2 H H 0 124 / N- H H 15 N CF2 HCF2 CH2 H H 0 125 N
N CP2 CF2 CF2 CH H H N- 0 H H 126/
N CF3 CFHCF2 C H H N- 0 H H 127 H 2 /
N CF2HCH , H H N-~N H H 128 /- S CF3 ______
N CP 3 CF2 CHQ H H N-N H H 129
______s CF3 _ _ _ _ _ N CF2 HCF2 CH- H H N-~N H H 130 J s CF 3
N CF3 CFPCF2 CH H H N-N H H
131 2 - s CF 3 ______
N CF3 CPHCF2 0 H H IN-N H H 132 H2 S CF 3 ______
[02 50]
Table 19
[Table 19] 225
H 13 N CE5,HCH 2 H 0-'N1 H H
H 14 N CF3CF2 .CH2 H O N - H H
H H 15 N CF2 HCF2 CH9 H N - H
H H 16 N CFBOF2 CF 2 CH2 H N -. H
H H 17 N CR3OFHOE2 CH2 H NN . H
137 FHH -N zI
H 139__ v FcFC2 N' Nzz__ CI H
H 10 N CF2HCF2H 2 H N zz7CI H H 138
-N
N CF3 CCF2 CH 2 H N~ C I H H H
140 N [0251N
Table 20______v~ __
NTbl C2C0C 2 H HN I 226
Present A R1 0c R 0 R302 R303 R R compound
N CF2 HCH2 H N OCH3 H H H 14 3 -- N \__ N H N CF 3CF 2CH2 H N OCHa H H 144 -- N I______\-N
N CF2 HCF2 CH 2 H N OCH, H H H 145~ ~. H N CFJCF2CF 2 CH 2 H ,N OCH3 H H 146 -N
N CF CFHCF CH H N OCH3 H H H 147--N 3 2 2
N CF2 HCH2 H -N NH2 H H H 14-N
N CF 3CF2 CH2 H N NH 2 H H H 14\9 -N
N CF2 HCF2 CH 2 H N NH 2 H H H 150 -N \ N H N CF 3CF2CF 2CH 2 H N NH 2 H H 151 N
N CF 3CFHCF2 CH 2 H N NH2 H H H 152 ~NNN______N
[02521
Table 21
[Table 21]
Present A R R R 2' R303 R R compound
N CF2 HCH 2 H IN S(O) 2CH 3 H H H 153 .- N \-N
N CF 3CF2 CH 2 H N S(0) 2CH 3 H H H 154 •-N N______\--N
N CF 2HCF 2 CH2 H N S(0)2CH 3 H H H 155• \-- N
N CF3CF2 CF 2CH 2 H N S(0) 2CH 3 H H H 156 -N N H N CF 3CFHCF2 CH- H N S(0) 2CH3 H H 157N
______N _ _ _ _ _ 227
H H H 18N CF2IHCH H -N ON -N H H H 19N CP2 CP2 CH 2 H N OzzrN
H H 10N CP),HCF 2CH2 H p Nz ON H 160 H H 11N CP 3CE 2 CFQCH2 H -N OrN H
H H 12N CF'3 CFHCF2 CH2 H -N~ O: N H 162 -N
[025 31
Table 22
[Table 223
Present Al R10R30 02R compound ______H H 13N CF2 HCH 2 H -lrCF 3 H -N ______. .... N...... H H 14N CP 3 CF2 CH2 H CF3 H
164 -N H H 16N CP2CF2CF2H2 H CF3 H 165 -N H H 17N CF3CF2 CF2 CH2 H Nlz CF3 H
H H 19 N CF3CFH 2 CH2 HN CF3 H
H H 10 N CF 2HCFH2 H N OF3 H
H H 11 N CF3 CF 2 CH H N~ CF3 H
H H H 12N CF3CFHCF2 CH 2 H N CF3
[02543 228
Table 23
[Table 23] Present A R ° R3 R302 RTc7 R R602 compound N CFHCH, H 3 . NN H H H 17 3-N
N CF 3CF2CH2 H ,N zN H H H 174 •-N N CF2HCF2CH, H NaN H H H 175 N
N CF3CF2CF2CH 2 H NRN H H H 176 •-N N CF3CFHCF2CH2 H N zN H H H 177 -- N N CF2HCH2 H IN H H H 178 +-N ,N N CF3CF2CH2 H N H H H 179 N
N CF9 HCF2CH2 H N H H H 180 -- N,1 N CF3CFCF2CH2 H N H H H 181 -N
N CF3CFHCF2,CH2 H IN H H H 182 •-N N I
[0255]
Table 24
5 [Table 24] Present A R R R0 3303 R R compound N CF2HCH. H N- H H H 183 N N CF3CF2CH2 H N- 0 H H H 184 N 229
N CF2HCF2CH2 H N- 0 H H H
185N N CF3CFPCF2CH2 H N- 0 H H H 186 N N CF3CFHCF2CH 2 H N- 0 H H H 187 •/
N CF2HCH 2 H N'N H H H 188 j C S1 CF 3 N CF2CF2CH 2 H N-N H H H 189 SCF3 N CF2HCF2 CH 2 H N-N H H H 190 SCF3 N CF3CF2 CF2CH 2 H N-N H H H 191
sj CF ___ 3 __ __
N CFBCPHCF2CH 2 H N-N H H H 192
I CF 3 [0256]
Table 25
[Table 25] Present A R 303 R compound F H H H 193 N CF2 HCH2 H
19N CF3CF2CH2 H F H H H
N CF2HCF2 CH2 H F H H H
N CF3CF 2CF2CH 2 H H H H
N CF3CFHCF2CH2 H F H H H
19N CF2HCH2 H CI H H H
N CF3 CF2 CH 2 H C H H H 230
200 N CF2 HCF2 CH2 H G- H H H
201 N CF3 CF2 CF2 CH 2 H H H H
202 N CF3 CFHCF2 CH 2 H H H H
Table 26
[Table 26] Present A' R'0 0 R3 0 1 R3 02 R3 03 R6 0 1 R6 02 campaund H H 23 N CF2 HCH 2 H -& NH 203 N/ F3FH2H aCNHHH
H H 25 N CF2CF2 CH2 H -&C H 204 N H aCNHHH/FC2C2H
H H 27N CF3CHCF2 CH 2 H -C H 205 N /FHHCN3 H
- F H H H 29N CF3 CF2 CF2H 2 H 210 N CFHF2H H -0 CN3H
C3H H H 21N CF3 CFHCF2 CH 2 H -a
H H H 22N CF3 CCF2 CH2 H -- F
21 n1 A1CF . 3 231
N CF2HCH2 H F H H H 213
N CF 3CF2CH 2 H F H H H 214
N CF2HCF 2CH 2 H F H H H 215
N CF3CF2CF2CH2 H F H H H 216
N CF3CFHCF2CH2 H F H H H 217
N CF 2HCH2 H CN H H H 218
N CF3CF2CH2 H CN H H H 219
N CF2 HCF2 CH2 H CN H H H 220
N CF3CF2 CF 2 CH2 H CN H H H 221
N CF3CFHCF2CH 2 H CN H H H 222
[0259]
Table 28
[Table 28] 232
Present A 1 10 P, t R $017 RP 303 P 601 602 compound ______
N CP¼HCHI H - H H H 223
N PCF2CH H - H H H 224 2 ______N__ _
N CF2HCF2CH2 H - H H H 225
N CF3CF2CF2 CH2 H - H H H 226 ______N ___ _ _
- H H H 27N CF2 CEHCF2CH2 H 228
N CF 2CH 2 H -N H H H 229
N CF 3 CF2CH 2 H -N H H H 229
N CE' 2 HCF2CH, H -N H H H 230
N CF3CFHCP 2CH2 H -N H H H 232
[02601
Table 29
[Table 29} Present A' RO 302 RP303R601R c2 campaund ______N CF2HICH 2 H -N H H H 233_
24N CF3CFhCH, H -N H H H 234/ H H 25N C-F,HOF3 CH2 H -N H
H H H 26N CF3CF2CP 2CH2 H -N 233
H 27N CP3CFHCF2CH2 H -N H H 237
N CF2HCH 2 H -N H H H 238 -- C/
N CF3CF2 CH2 H -N H H H 239
______\__N _ _ H H 20N CP2HCE 2CHQ H -N H
N CF3CF2CBCH 2 H ~ .. N H H H 241 /
N CF3CFHCF2CH2 H -N H H H 242 -< /
[0261]
Table 30
[Table 30] Present A 1 Ri100 7~0 3 R0 2 R 3Rr601RH6 2
JN ~CF2HCH2 H CF3 H {H H 243
______N___ N CP3CP 2CH2 H CF3 H H H 244
N CF 2HCF2CH9, H CF3 H H H 245
______~N___ _ N CF3CF2CP 2CH 2 H CF3 H H H 246
______~ N______N CF3CFHCF2CH? H CF3 H H H 247
______N _ _ ___
28N CFHCH2 H - F H H H
29N CF3CF2 CH2 H -CF H H H 234
F3H H H 20N CF2 HCP2 CH 2 H
C3H H H 21N CF3CW 2 CP 2 CH2 - H
- F H H H 22N CF3 CEHCFOCH< H
[02 621
Table 31
[Table 31] Present A I R l-R31 R32R 0 01RCl compound:__
23N CF2 HCH2 H -NH H
N CF2 CP2CH 2 H -N H H H 254 \/ F
_ .___ __ ...... N __ N CF2 HCF2 CH2 H -N H H H 255 -\ F
______~~ N______N CP3OP12CF2 CH 2 H -N H H H 256 \/>-F
______N ______N CF3 CFHCF2 CH2 H -N H H H 257 -C/F
______N _ _ _ _ N CF2HCH2 H ND H H H 258 -<
N CE2CP2 CH2 H N-7 H 259 <\/
N CP12HCP 2CH2 H N- H H H 260 -1D
N CE' 3OF2CF 2CHQ H N- H H H 261 -- \
22N CF 3CFHCF 2CH 2 H N-7
[0263]
5 Table 32 235
[Table 32] Present A R R R R R compound 7 N CF2HCH 2 H CF 3 H H H 263 -N; 0 N CF3CF2CH2 H CF3 H H H 264 •N /
N CF2HCF2CH2 H CF3 H H H 265 -N /
N CF3CF2CF2CH2 H CF 3 H H H 266 -N
N CF3CFHCF2CH2 H CF3 H H H 267 -N /
[0264]
Table 33
[Table 33]
Present A R10 P1 R302 R R o 602 compound 268 N CF2HCH 2 H OCH3 H H H 269 N CF3CF2CH2 H OCH3 H H H 270 N CF2HCF2CH2 H OCH3 H H H 271 N CF3CF2CF2 CH2 H OCH3 H H H 272 N CF3CFHCF2CH2 H OCH 3 H H H 273 N CF2HCH2 H OCHCH3 H H H 274 N CF3CF2CH2 H OCH2CH3 H H H 275 N CF2HCF2CH2 H OCH2CH3 H H H 276 N CF3CF2CF2CH2 H OCH2CH,3 H H H 277 N CF3CFHCF2CH, H OCH2CH3 H H H 278 N CF2HCH2 H OCH (CH3)2 H H H 279 N CF3CF2CH2 H OCH(CH3) H H H 236
280 N CF 2HCF 2 CH2 H OCH (CH 3 ) 2 H H H
281 N CF 3CF 2 CF2 CH2 H OCH(CH 3 ) 2 H H H
282 N CF 3CFHCF2 CH 2 H OCH (CH 3 ) 2 H H H
283 N CF 2HCH 2 H OCH 2 CH2N(CH 3 )2 H H H
284 N CF 3CF 2 CH2 H OCH 2 CH2N (CH 3 2 H H H
285 N CF 2HCF 2 CH2 H OCH 2 CH2N(CH 3 )2 H H H
286 N CF 3CF 2 CF2 CH2 H OCH 2 CH2N(CH 3 )2 H H H
287 N CF 3CFHCF2 CH 2 H OCH 2 CH2N (CH 3 2 H H H 288 N CF 2HCH 2 H OCH 2 CF3 H H H 289 N CF 3CF 2 CH2 H OCH 2 CF3 H H H 290 N CF 2HCF 2 CH2 H OCH 2 CF3 H H H 291 N CF 3CF 2 CF2 CH2 H OCH 2 CF3 H H H 292 N CF 3CFHCF2 CH 2 H OCH 2 CF3 H H H [0265] Table 34 [Table 34] Present Al R' 0 0 R3 0 1 R 3 0 2 R3 0 3 R 6 01 R60 2 compound 293 N CF2 HCH 2 H OCH2 CF 3 H H H
294 N CF3 CF 2CH 2 H OCH2 CF 3 H H H 295 N CF2 HCF 2 CH2 H OCH2 CF 3 H H H 296 N CF3 CF 2CF 2 CH2 H OCH2 CF 3 H H H 297 N CF3 CFHCF2 CH2 H OCH2 CF 3 H H H 298 N CF2 HCH 2 H OCH2 CF 2CF 2 H H H H
299 N CF3 CF 2CH 2 H OCH2 CF 2CF 2 H H H H 300 N CF2 HCF 2 CH2 H OCH2 CF 2CF 2 H H H H 301 N CF3 CF 2CF 2 CH2 H OCH2 CF 2CF 2 H H H H 302 N CF3 CFHCF2 CH2 H OCH2 CF 2CF 2 H H H H 303 N CF2 HCH 2 H OCH2 CF 2CF 3 H H H
304 N CF3 CF 2CH 2 H OCH2 CF 2CF 3 H H H 305 N CF2 HCF 2 CH2 H OCH2 CF 2CF 3 H H H 306 N CF3 CF 2CF 2 CH2 H OCH2 CF 2CF 3 H H H 307 N CF3 CFHCF2 CH2 H OCH2 CF 2CF 3 H H H 308 N CF2 HCH 2 H NHC(O)CH 3 H H H
309 N CF3 CF 2CH 2 H NHC (O) CH3 H H H 310 N CF2 HCF 2 CH2 H NHC(O)CH 3 H H H 311 N CF3 CF 2CF 2 CH2 H NHC (O) CH3 H H H 312 N CF3 CFHCF2 CH2 H NHC (0) CH3 H H H 313 N CF2 HCH 2 H NHC (O) CH2 CH 3 H H H
314 N CF3 CF 2CH 2 H NHC (0) CH2 CH 3 H H H 315 N CF2 HCF 2 CH2 H NHC (0) CH2 CH 3 H H H 316 N CF3 CF 2CF 2 CH2 H NHC (O) CH2 CH 3 H H H 317 N CF3 CFHCF2 CH2 H NHC (0) CH2 CH 3 H H H
/ n A 1 1 1\ 1.nr 237
[0266]
Table 35
[Table 35]
30 3 0 Present Al R D°R 1 R 2 R303 R |R62 compound N CF2HCH2 H -NH H H H 318
N CF3CF2CH2 H -NH H H H 319
N CF2HCF2CH2 H -NH H H H 320
N CF3CF2CF2CH2 H -NH H H H 321
N CF3CFHCF2CH2 H -NH H H H 322
N CF2HCH2 H CH3 H H H 323 N
N CF3CF2CH 2 H OCH3 H H H 324 C-N
N CF2HCF2CH2 H CH3 H H H 325 -N
N CF3CF 9CF2CH2 H CH 3 H H H 326 -N
N CF3CFHCF2CH 2 H CH 3 H H H 327 -N
[0267]
5 Table 36
[Table 36] Present A R° R R 2 R compound 328 N I CF2HCH 2 H NHC (O) OCH 3 H H 238
329 N CF 3 CF2 CH2 H NHC(O)OCH 3 H H H 330 N CF 2 HCF2 CH2 H NHC(O)OCH 3 H H H 331 N CF 3 CF2 CF2 CH2 H NHC(O)OCH 3 H H H 332 N CF 3 CFHCF2CH 2 H NHC(O)OCH 3 H H H 333 N CF 2 HCH2 H NHC (O) OCH 2 CH3 H H H 334 N CF 3 CF2 CH2 H NHC (0) OCH 2 CH3 H H H 335 N CF 2 HCF2 CH2 H NHC (0) OCH 2 CH3 H H H 336 N CF 3 CF2 CF2 CH2 H NHC (O) OCH 2 CH3 H H H 337 N CF 3 CFHCF2CH 2 H NHC(0)OCH 2 CH3 H H H 338 N CF 2 HCH2 H OCH 2 CH2 CH3 H H H 339 N CF 3 CF2 CH2 H OCH 2 CH2 CH3 H H H 340 N CF 2 HCF2 CH2 H OCH 2 CH2 CH3 H H H 341 N CF 3 CF2 CF2 CH2 H OCH 2 CH2 CH3 H H H 342 N CF 3 CFHCF2CH 2 H OCH 2 CH2 CH3 H H H [0268]
A compound represented by formula (M-100)
R601 V R301
R 100 0 -N/ \ N- - A'- R 602 R303
(M-100)
[wherein, R3 0 1 , R 3 0 2 , R 3 0 3 , R6 0 1 , R 60 2 , R1 0 0 , A', and V represent
5 any combination indicated in the Table 37 below.]
can be prepared according to the processes described above.
[0269]
Table 37
[Table 37]
2 Intermediate A' V R1 0 0 R 3 0 1 R3 0 2 R3 0 3 R 6 01 R 60 compound
a-1 N F CF3 CH2 H H H H H a-2 N F CF2HCH2 H H H H H a-3 N F CF3CF2 CH2 H H H H H a-4 N F CF2 HCF2 CH 2 H H H H H
/ n n 1 /I 1 1 \ .nI I 239
a-5 N F CF3 CF2 CF2 CH 2 H H H H H a-6 N F CF3 CFHCF2 CH2 H H H H H a-7 N F CF2 HCF2 CF 2CF 2 CH2 H H H H H a-8 N Cl CF3 CH2 H CF3 H H H a-9 N Cl CF2 HCH2 H CF3 H H H a-10 N Cl CF3 CF2 CH2 H CF3 H H H a-11 N Cl CF2HCF2CH 2 H CF3 H H H a-12 N Cl CF3 CF2 CF2 CH 2 H CF3 H H H a-13 N Cl CF3 CFHCF2 CH2 H CF3 H H H a-14 N Cl CF2HCF2CF 2CF 2CH2 H CF3 H H H a-15 CH F CF3 CH2 H CF3 H H H a-16 CH F CF2HCH2 H CF3 H H H a-17 CH F CF3CF2CH2 H CF3 H H H a-18 CH F CF2 HCF2 CH 2 H CF3 H H H a-19 CH F CF3CF2CF2CH 2 H CF3 H H H a-20 CH F CF3CFHCF 2CH2 H CF3 H H H a-21 CH F CF2 HCF2 CF 2CF 2 CH2 H CF3 H H H [0270]
A compound represented by formula (M-200)
R601 HS R301
R 100 0 -N/ \ N-- Al R 602 R303
(M-200)
[wherein, R 3 0 1 , R 3 0 2 , R3 0 3 , R6 0 1 , R 60 2 , R1 0 0 , and A' represent
5 any combination indicated in the Table 38 below.]
can be prepared according to the processes described above.
[0271] Table 38 [Table 38]
3 6 0 60 2 Intermediate A' R1 0 0 R3 0 1 R 30 2 R 0 3 R 1 R compound
b-1 N CF3 CH2 H H H H H
/ n n 1 /I 1 1 \ nri 240
b-2 N CF2HCH2 H H H H H
b-3 N CF 3CF2 CH2 H H H H H b-4 N CF2 HCF2CH 2 H H H H H b-5 N CF3CF2 CF 2CH 2 H H H H H b-6 N CF3CFHCF2 CH 2 H H H H H b-7 N CF2 HCF2CF2CFCH 2 H H H H H b-8 N CF3CH, H CF3 H H H b-9 N CF2HCH2 H CF3 H H H b-10 N CF3CF2CH2 H CF3 H H H b-11 N CF2HCF2CH2 H CF3 H H H b-12 N CFCF2CF2CH2 H CF3 H H H b-13 N CF3CFHCF2CH2 H CF3 H H H b-14 N CF2HCF2CF2CF2CH2 H CF3 H H H b-15 CH CF3CH2 H CF3 H H H b-16 CH CF2HCH2 H CF3 H H H b-17 CH CF3CF2CH2 H CF3 H H H b-18 CH CF,HCF2CH2 H CF3 H H H b-19 CH CF3CF2CF2CH, H CF3 H H H b-20 CH CF3CFHCF2CH2 H CF3 H H H b-21 CH CF2HCF2CF2CF2CH2 H CF3 H H H [0272]
A compound represented by formula (M300)
R200 R601 (O)nS R 301
HO R 302 N~- Al R602 R303 (M-300)
[wherein, R301, R3C2, R303, RE01, R602, R1° , and A' represent
5 any combination indicated in the Table 39 below.]
can be prepared according to the processes described above.
[0273]
Table 39
[Table 39]
Intermediate [A R n Rm R302 R0 RC1 R"7 241
compound c-1 N CH3 2 H H H H H c-2 N CH3CH 2 2 H H H H H c-3 N CH3CH 2CH 2 2 H H H H H c-4 N CH (CH 3) 2 2 H H H H H c-5 N CF3CH 2 2 H H H H H c-6 N 2 H H H H H c-7 N 2 H H H H H
c-8 N CH3 2 H CF3 H H H c-9 N CH3CH 2 2 H CF3 H H H c-10 N CH3CH 2CH 2 2 H CF3 H H H c-11 N CH (CH 3 ) 2 2 H CF3 H H H c-12 N CF3CH 2 2 H CF3 H H H c-13 N 2 H CF3 H H H
c-14 N 2 H CF3 H H H
c-15 CH CH3 2 H CF3 H H H c-16 CH CH3CH 2 2 H CF3 H H H c-17 CH CH3CH 2CH 2 2 H CF3 H H H c-18 CH CH (CH 3 ) 2 2 H CF3 H H H c-19 CH CF3CH 2 2 H CF3 H H H c-20 CH 2 H CF3 H H H
c-21 CH 2 H CF3 H H H
[0274]
A compound represented by formula (M400)
R601 (O),S R 30 1
V R 2 N- -- A R602 R33 (M-400)
/ n n 1 /I 1 1 \ .nrriv- 242
[wherein, R3 0 1 , R3 0 2 , R3 0 3 , R6 0 1 , R6 0 2 , R 20 0 , V and A' represent
any combination indicated in the Table 40 below.]
can be prepared according to the processes described above.
[0275]
5 Table 40
[Table 40]
Intermediate A' V R2 0 0 n R3 0 1 R3 0 2 R 3 03 R 6 0 1 R 60 2 compound
d-1 N Cl CH3 2 H H H H H
d-2 N Cl CH3 CH 2 2 H H H H H
d-3 N Cl CH3 CH 2CH 2 2 H H H H H
d-4 N Cl CH (CH 3 ) 2 2 H H H H H
d-5 N Cl CF3 CH 2 2 H H H H H d-6 N Cl 2 H H H H H
d-7 N Cl 2 H H H H H
d-8 N Cl CH3 2 H CF 3 H H H
d-9 N Cl CH3 CH 2 2 H CF 3 H H H
d-10 N Cl CH3 CH 2CH 2 2 H CF 3 H H H
d-11 N Cl CH (CH 3 ) 2 2 H CF 3 H H H
d-12 N Cl CF3 CH 2 2 H CF 3 H H H
d-13 N Cl 2 H CF 3 H H H
d-14 N Cl 2 H CF 3 H H H
d-15 CH Cl CH3 2 H CF 3 H H H
d-16 CH Cl CH3 CH 2 2 H CF 3 H H H
d-17 CH Cl CH3 CH 2CH 2 2 H CF 3 H H H
d-18 CH Cl CH (CH 3 ) 2 2 H CF 3 H H H
d-19 CH Cl CF3 CH 2 2 H CF 3 H H H
d-20 CH Cl 2 H CF 3 H H H
/ n n 1 /I 1 1 \ .nr1 243
d-21 CH Cl 2 H CF 3 H H H
[0276]
A compound represented by formula (M330)
R 200
R601 (O)nS
4 -N R 00 / N- 0
(M-330)
[wherein, R6 0 1 , R 6 o 2 , R 20 o and R 4 00 represent any combination
5 indicated in the Table 41 to Table 43 below.]
can be prepared according to the processes described above.
[0277]
Table 41
[Table 41]
Intermediate R4 00 R20o n R 6 0 1 R 60 2 compound
e-1 F CH 3 2 H H e-2 Cl CH 3 2 H H e-3 Br CH 3 2 H H e-4 CH 30 CH 3 2 H H
e-5 CH 3CH 2 0 CH 3 2 H H
e-6 CF 3CH(CH 3 ) CH 3 2 H H
e-7 CF 3CF 2 CH(CH3 ) CH 3 2 H H
e-8 CF 3CH 2 CH 3 2 H H
e-9 CF 2HCH 2 CH 3 2 H H
e-10 CF 3CF 2 CH2 CH 3 2 H H
e-11 CF 2HCF 2 CH2 CH 3 2 H H
e-12 CF 3CF 2 CF2 CH2 CH 3 2 H H
e-13 CF 3CFHCF2 CH 2 CH 3 2 H H
e-14 CF 2HCF 2 CF2 CF2 CH 2 CH 3 2 H H e-15 F CH 3 CH2 2 H H e-16 Cl CH 3 CH2 2 H H
/ n n 1 /I 1 1 \ .nr1 244
e-17 Br 0H 30H 2 2 H H e-18 CH3 0 0H 30H 2 2 H H e-19 0H3 0H2 0 0H 30H 2 2 H H e-20 CF3 CH(OH3 ) 0H 30H 2 2 H H e-21 CF3 CF2 CH(OH3 ) 0H3 0H2 2 H H e-22 0F30H2 0H 30H 2 2 H H e-23 CF 2 HCH2 0H 30H 2 2 H H e-24 0F 30F20H2 0H 30H 2 2 H H e-25 CF2 HCF2 CH2 0H 30H 2 2 H H e-26 0F 3 0F2 0F20H2 0H 30H 2 2 H H e-27 CF3 CFHCF2 CH2 0H 30H 2 2 H H e-28 CF2 HCF2 CF2 CF2 CH 2 0H 30H 2 2 H H [0278]
Table 42
[Table 42] 6 0 602 Intermediate R4 00 R20 n R 1 R campaund e-29 F 2 H H e-30 Cl 2 H H e-31 Br 2 H H e-32 CH3 0 2 H H e-33 0H3 0H2 0 2 H H e-34 CF3 CH(OH3 )2 H H e-35 CF3 CF2 CH(OH3 ) 2 H H e-36 0F3 0H2 2 H H e-37 CF 2 HCH2 2 H H e-38 0F30F20H2 2 H H e-39 CF2 HCF2 CH2 2 H H e-40 0F3 0F2 0F20H2 2 H H e-41 CF3 CFHCF2 CH2 2 H H 245
e-42 CF2HCF 2CF2CF2CH 2 2 H H
[02 79]
Table 43
[Table 43] 60 602 Intermediate R4 0 0 R20n R 1 R compound
e-43 F 2 H2 H
e-44 Cl V- 2 H H
e-45 Br V 2 H H
e-46 CH 30 2 H H
e-47 CH 3CH 2O 2 H H
e-48 CF3CH (OH3 )V 2 H H
e-49 CF3CF2CH (CHA)" 2 H H
e-50 CF 3CH2 vl 2 H H
e-51 CF 2HCH2 vl 2 H H
e-52 CF 3CF2CH2 v 2 H H
e-53 CF 2HCF 2CH2 vl 2 H H
e-54 CF 3CF 2CF 2CH2 l- 2 H H
e-55 CF3 CFHCF2CH2 vl 2 H H
e-56 CF2HCF 2CF2CF2CH2 vl 2 H H
[0280]
5 A compound represented by formula (M331)
R60 1 (0),,S
N- NH 2 R602 (M-331) 246
[wherein, R6 0 1 , R 6 0 2 , R 20 0 and R 4 0 0 represent any combination
indicated in the Table 44 to Table 46 below.]
can be prepared according to the processes described above.
[0281]
5 Table 44
[Table 44]
Intermediate R 4 00 R20o n R6 0 1 R60 2 compound
f-1 F CH3 2 H H f-2 Cl CH3 2 H H f-3 Br CH3 2 H H f-4 CH 30 CH3 2 H H f-5 CH 3CH 2 0 CH3 2 H H
f-6 CF 3CH (CH 3 ) CH3 2 H H
f-7 CF 3CF 2 CH (CH 3 ) CH3 2 H H f-8 CF 3CH 2 CH3 2 H H f-9 CF 2HCH 2 CH3 2 H H f-10 CF 3CF 2 CH2 CH3 2 H H f-11 CF 2HCF 2 CH2 CH3 2 H H f-12 CF 3CF 2 CF2 CH2 CH3 2 H H f-13 CF 3CFHCF2 CH 2 CH3 2 H H f-14 CF 2HCF 2 CF2 CF2 CH 2 CH3 2 H H f-15 F CH3 CH 2 2 H H f-16 Cl CH3 CH 2 2 H H f-17 Br CH3 CH 2 2 H H f-18 CH 30 CH3 CH 2 2 H H f-19 CH 3CH 2 0 CH3 CH 2 2 H H
f-20 CF 3CH (CH 3 ) CH3 CH 2 2 H H
f-21 CF 3CF 2 CH (CH 3 ) CH3 CH 2 2 H H f-22 CF 3CH 2 CH3 CH 2 2 H H
f-23 CF 2HCH 2 CH3 CH 2 2 H H f-24 CF 3CF 2 CH2 CH3 CH 2 2 H H f-25 CF 2HCF 2 CH2 CH3 CH 2 2 H H f-26 CF 3CF 2 CF2 CH2 CH3 CH 2 2 H H f-27 CF 3CFHCF2 CH 2 CH3 CH 2 2 H H f-28 CF 2HCF 2 CF2 CF2 CH 2 CH3 CH 2 2 H H [0282]
/ n n 1 /I 1 1 \ .nr1 247
Table 45
[Table 45]
Intermediate R4 00 R20o n R 6 01 R 60 2 compound
f-29 F 2 H H
f-30 Cl 2 H H
f-31 Br 2 H H
f-32 CH 30 2 H H
f-33 CH 3CH 2 0 2 H H
f-34 CF 3CH (CH 3 ) 2 H H
f-35 CF 3CF 2 CH (CH 3 ) 2 H H
f-36 CF 3CH 2 2 H H
f-37 CF 2HCH 2 2 H H
f-38 CF 3CF 2 CH2 2 H H
f-39 CF 2HCF 2 CH2 2 H H
f-40 CF 3CF 2 CF2 CH2 2 H H
f-41 CF 3CFHCF2 CH 2 2 H H
f-42 CF 2HCF 2 CF2 CF2 CH 2 2 H H
[0283]
Table 46
5 [Table 46]
Intermediate R4 00 R20o n R 6 01 R 60 2 compound
f-43 F 2 H H
f-44 Cl 2 H H
/ n n 1 /I 1 1 \ .nI I 248
f-45 Br 2 H H
f-46 CH 30 2 H H
f-47 CH 3CH 20 2 H H
f-48 CF 3CH (CH3 ) 2 H H
f-49 CF 3CF 2 CH (CH3 ) 2 H H
f-50 CF 3CH 2 2 H H
f-51 CF 2HCH 2 2 H H
f-52 CF 3CF 2CH2 2 H H
f-53 CF 2HCF 2CH2 2 H H
f-54 CF 3CF 2CF2CH2 2 H H
f-55 CF 3CFHCF2 CH 2 2 H H
f-56 CF 2HCF 2CF2CF2CH 2 2 H H
[0284]
Next, the formulation examples of the Present compound
are shown below. The ''parts'' represents ''part by
weight'' unless otherwise specified.
5 [0285]
Formulation Example 1
Into a mixture of 35 parts of xylene and 35 parts of
DMF, 10 parts of each of the Present compounds 1 to 348 is
dissolved, and then 14 parts of polyoxyethylene styryl
/ n n 1 /I 1 1 \ .nI I 249
phenyl ether and 6 parts of calcium dodecylbenzene
sulfonate are added, followed by mixing them to obtain each
formulation.
[0286)
5 Formulation Example 2
Four (4) parts of sodium lauryl sulfate, 2 parts of
calcium lignin sulfonate, 20 parts of synthetic hydrated
silicon oxide fine powder and 54 parts of diatomaceous
earth are mixed, and further 20 parts of each of the
10 Present compounds 1 to 348 is added, followed by mixing
them to obtain each wettable powders.
[0287]
Formulation Example 3
To 2 parts of each of the Present compounds 1 to 348,
15 1 part of synthetic hydrated silicon oxide fine powder, 2
parts of calcium lignin sulfonate, 30 parts of bentonite
and 65 parts of kaolin clay are added, followed by mixing,
granulation with a granulator and forced-air drying to
obtain each granular formulation.
20 [0288]
Formulation Example 4
Into an appropriate amount of acetone, 1 part of each
the Present compounds 1 to 348 is mixed, and then 5 parts
of synthetic hydrous silicon oxide fine powder, 0.3 parts
25 of isopropyl acid phosphate and 93.7 parts of kaolin clay 250
are added, followed by mixing with stirring thoroughly and
removal of acetone from the mixture by evaporation to
obtain each of powder formulation.
[0289]
5 Formulation Example 5
A mixture of 35 parts of polyoxyethylene alkyl ether
sulfate ammonium salt and white carbon (weight ratio of
1:1), 10 parts of each of the Present compounds 1 to 348,
and 55 parts of water are mixed, followed by finely
10 grounding by a wet grinding method to obtain each flowable
formulation.
[0290]
Formulation Example 6
Into a mixture of 5 parts of xylene and 5 parts of
15 trichloroethane, 0.1 parts of each of the Present compounds
1 to 348 is dissolved, and the resulting mixture is then
mixed with 89.9 parts of kerosene to obtain each oil
solution.
[0291]
20 Formulation Example 7
Into 0.5 mL of acetone, 10 mg of each of the Present
compounds 1 to 348 is dissolved and the solution is added
dropwise to 5 g of a solid feed powder for an animal (solid
feed powder for rearing and breeding CE-2, manufactured by
25 CLEA Japan, Inc.), followed by mixing the resulting mixture 251
uniformly, and then by drying them by evaporation of
acetone to obtain each poison bait.
[0292)
Formulation Example 8
5 Into an aerosol can, 0.1 part of each of the Present
compound 1 to 348 and 49.9 parts of Neothiozole (Chuo Kasei
Co., Ltd.) are placed. After mounting an aerosol valve, 25
parts of dimethylether and 25 parts of LPG are filled,
followed by shaking and further mounting an actuator to
10 obtain an oily aerosol.
[0293]
Formulation Example 9
A mixture of 0.6 part of each of the Present compounds
1 to 348, 0.01 part of BHT (2,6-di-tert-butyl-4
15 methylphenol), 5 parts of xylene, 3.39 parts of deodorized
kerosine and 1 part of an emulsifier {Rheodol MO-60
(registered trademark of Kao Corporation)} and 50 parts of
distilled water are filled into an aerosol container, and a
valve part is attached. Then, 40 parts of a propellant
20 (LPG) is filled therein through the valve under pressure to
obtain an aqueous aerosol.
[0294]
Formulation Example 10
Zero point one (0.1) parts of each of the Present
25 compounds 1 to 348 are mixed into 2 mL of propylene glycol, 252
and the resulting solution is impregnated into a ceramic
plate having a size of 4.0 cm x 4.0 cm and a thickness of
1.2 cm, to obtain thermal fumigants.
[0295]
5 Formulation Example 11
Five (5) parts of each of the Present compounds 1 to
348, and 95 parts of ethylene-methyl methacrylate copolymer
(the ratio of the methyl methacrylate in the copolymer: 10
weight %), Acryft (registered by trademark) WD 301,
10 manufactured by Sumitomo Chemical Co. Ltd.) are melted and
kneaded with a closed type pressure kneader, and the
resulting kneaded product is extruded from an extrusion
molding machine through a molding die to obtain a rod
shaped molded product having a length of 15 cm and a
15 diameter of 3 mm.
[0296]
Formulation Example 12
Five (5) parts of each of the Present compounds 1 to
348, and 95 parts of plasticized polyvinyl chloride resin
20 are melted and kneaded with a closed type pressure kneader,
and the resulting kneaded product is extruded from an
extrusion molding machine through a molding die to obtain a
rod-shaped molded product having a length of 15 cm and a
diameter of 3 mm.
25 [0297] 253
Formulation Example 13
One hundred (100) mg of each of the Present compounds
1 to 348, 68.75 mg of lactose, 237.5 mg of corn starch,
43.75 mg of microcrystalline cellulose, 18.75 mg of
5 polyvinylpyrrolidone, 28.75 mg of sodium carbomethyl starch
and 25 mg of magnesium stearate are mixed, and the
resulting mixture was compressed to an appropriate size to
obtain a tablet.
[0298]
10 Formulation Example 14
Twenty five (25) mg of each of the Present compounds 1
to 348, 60 mg of lactose, 25 mg of corn starch, 6 mg of
carmellose calcium and an appropriate amount of 5% of
hydroxypropyl methylcellulose are mixed, and the resulting
15 mixture are filled into a hard shell gelatin capsule or a
hydroxypropyl methylcellulose capsule to obtain capsules.
[0299]
Formulation Example 15
To 100 mg of each of the Present compounds 1 to 348,
20 500 mg of fumaric acid, 2000 mg of granulated sugar, 13,000
mg of sorbitol (70% solution), 100 mg of Veegum K
(manufactured by Vanderbilt Co.), 35 mg of perfume and 500
mg of coloring agent, a distilled water is added so that a
final volume is set to be 100 mL, followed by mixing them
25 to obtain a suspension for oral administration. 254
[0300]
Formulation Example 16
Into a mixture of 5% by weight of an emulsifier, 3% by
weight of benzyl alcohol and 30% by weight of propylene
5 glycol, 5% by weight of each of the Present compounds I to
348 is dissolved, and phosphate buffer is added thereto so
that a pH of the solution is set to be 6.0 to 6.5, and
water is added as the rest parts to obtain the solution for
oral administration.
10 [0301]
Formulation Example 17
To a mixture of 57% by weight of fractional
distillated palm oil and 3% by weight of polysorbate 85, 5%
by weight of aluminum distearate is added, and heated to
15 disperse it. The resulting mixture is cooled to room
temperature, and 25% by weight of saccharin is dispersed in
an oil vehicle. Ten (10) % by weight of each of the
Present compounds 1 to 348 is divided thereto to obtain a
paste for oral administration.
20 [0302]
Formulation Example 18
Five (5) % by weight of each of the Present compounds
1 to 348 is mixed with 95% by weight of limestone filler,
followed by a wet granulation of the resulting mixture to
25 obtain a granule for oral administration. 255
[0303]
Formulation Example 19
Into 80 parts of diethylene glycol monomethyl ether, 5
parts of each of the Present compounds 1 to 348 is
5 dissolved, and 15 parts of propylene carbonate is added
thereto, and the resulting mixture is mixed to obtain a
spot-on solution.
[0304]
Formulation Example 20
10 Into 70 parts of diethylene glycol monomethyl ether,
10 parts of each of the Present compounds 1 to 348 is
dissolved, and 20 parts of 2-octyldodecanol is added
thereto, and the resulting mixture is mixed to obtain a
pour-on solution.
15 [0305]
Formulation Example 21
To 0.5 parts of each of the Present compounds 1 to 348,
60 parts of Nikkol (registered by trademark) TEALS-42
(manufactured by Nikko Chemical Co. Ltd.: 42% of aqueous
20 solution of lauryl sulfuric acid triethanol amine) and 20
parts of propylene glycol are added, and the resulting
mixture is mixed with stirring thoroughly, and 19.5 parts
of water is then added thereto and the resulting mixture is
further mixed with stirring thoroughly to obtain a
25 hydrogenous solution of shampoo formulation. 256
[10306]
Formulation Example 22
Zero point fifteen (0.15)% by weight of each of the
Present compounds 1 to 348, 95% by weight of animal feed,
5 as well as 4.85% by weight of a mixture of dibasic calcium
phosphate, diatomaceous earth, aerosol and carbonate (or
chalk) are mixed with stirring thoroughly to obtain a
premix for animal feed.
[0307]
10 Formulation Example 23
Seven point two (7.2) g of each of the Present
compounds 1 to 348, and 92.8 g of Hosco (registered
trademark) S-55 (manufactured by Maruishi Pharmaceuticals)
are melted and mixed at 100 0 C, and the resulting mixture
15 was poured into a suppository mold, followed by performing
a cooling solidification to obtain a suppository.
[0308]
Next, Test Examples are used to show an efficacy of
the Present compound on controlling harmful arthropods.
20 The following test examples were carried out at 25°C.
[0309]
Test example 1
The test compounds are made to a formulation according
to a similar method to that described in the Formulation
25 Example 5, and thereto is added water containing 0.03 v/v % 257
of a spreader to prepare a diluted solution containing a
prescribed concentration of the test compound.
Cucumber (Cucumis sativus) seedling (on the
developmental stage of the second true leaf) is planted in
5 a polyethylene cup and approximately 30 heads of cotton
aphid (Aphis gossypii) (all stages of life) are released
onto the leaves of the cucumber. After I day, the diluted
solutions are sprayed into the seedling in a ratio of 10
mL/seedling. After 5 days, the number of the surviving
10 insects was examined and the controlling value was
calculated by the following equation.
Controlling value (%) = {1-(CbxTai)/(CaixTb)}xlOO
wherein the symbols in the formula represent the following
descriptions.
15 Cb: Number of the test insects in untreated group;
Cai: Number of the surviving insects at the time of
the investigation in untreated group;
Tb: Number of the test insects in treated group;
Tai: Number of the surviving insects at the time of
20 the investigation in treated group;
Here the ''untreated group'' represents a group where
the similar treatment procedure to that of the treated
group except not using the test compound is done.
[0310]
25 The results of the test that was done according to the 258
Test example 1 are shown below.
When the prescribed concentration was 500 ppm, the
treated group that was treated with each of the below
mentioned Present compounds showed 90% or greater as the
5 controlling value.
Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11,
12, 13, 14, 15, 16, 18, 19, and 24
[0311]
The results of the test that was done according to the
10 Test example 1 are shown below.
When the prescribed concentration was 200 ppm, the
treated group that was treated with each of the below
mentioned Present compounds showed 90% or greater as the
controlling value.
15 Present compound number: 2, 4, 5, 6, 7, 8, 9, 10, 11, 12,
13, 16, 18, and 24
(0312]
Test example 2
The test compounds are made to a formulation according
20 to a similar method to that described in the Formulation
Example 5, and thereto is added water to prepare a diluted
solution containing a prescribed concentration of the test
compound.
Cucumber seedling (on the developmental stage of the
25 second true leaf) is planted in a polyethylene cup, and the 259
diluted solutions in the ratio on 5 mL/seedling were
irrigated into the plant foot. After 7 days, approximately
30 heads of cotton aphid (all stages of life) were
inoculated onto the cucumber leaves. After additional 6
5 days, the number of the surviving insects was examined, and
the controlling value was calculated by the following
equation.
Controlling value (%) = {1-(CbxTai)/(CaixTb)}x100
wherein the symbols in the formula represent the following
10 descriptions.
Cb: Number of the test insects in untreated group;
Cai: Number of the surviving insects at the time of
the investigation in untreated group;
Tb: Number of the test insects in treated group;
15 Tai: Number of the surviving insects at the time of
the investigation in treated group;
Here the ' 'untreated group'' represents a group where
the similar treatment procedure to that of the treated
group except not using the test compound is done.
20 [0313]
The results of the test that was done according to the
Test example 2 are shown below.
When the prescribed concentration was 200 ppm, the
treated group that was treated with each of the below
25 mentioned Present compounds showed 90% or greater as the 260
controlling value.
Present compound number: 4, 5, 6, 8, 9, 10, 11, 12, 13, 16,
18, and 24 [0314] 5 Test exmaple 3
The test compounds are made to a formulation according
to a similar method to that described in the Formulation
Example 5, and thereto is added water containing 0.03 v/v %
of a spreader to prepare a diluted solution containing a
10 prescribed concentration of the test compound.
Rice (Oryza sativa) seedling (on the developmental
stage of the second true leaf) is planted in a polyethylene
cup, and the diluted solutions are sprayed into the
seedling in a ratio of 10 mL/seedling. Thereafter, 20
15 heads of 3rd instar larvae of brown planthopper
(Nilaparvata lugens) were released onto the rice leaves.
After 6 days, the number of the surviving insects was
examined, and the mortality was calculated by the following
equation.
20 Mortality (%) = {1- the number of the surviving
insects/20} x 100 [0315] The results of the test that was done according to the
Test example 3 are shown below.
25 When the prescribed concentration was 500 ppm, each of
the below-mentioned Present compounds showed 90% or greater
/ n n 1 /I 1 1 \ .nI I 261
as the controlling value.
Present compound number: 2, 4, 5, 6, 7, 8, 9, 10, 11, 12,
13, 14, 16, 18, 19,,21, and 24
[03163
5 The results of the test that was done according to the
Test example 3 are shown below.
When the prescribed concentration was 200 ppm, each of
the below-mentioned Present compounds showed 90% or greater
as the controlling value.
10 Present compound number: 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, 12,
13, 15, 16, 18, and 24
[0317]
Test example 4
The test compounds are made to a formulation according
15 to a similar method to that described in the Formulation
Example 5, and thereto is added water to prepare a diluted
solution containing a prescribed concentration of the test
compound.
The diluted solutions described above were added to
20 the polyethylene cup, and therein was installed Rice
seedling (on the developmental stage of the second true
leaf) that had been planted in a polyethylene cup having a
hole in the bottom. After 7 days, 20 heads of 3rd instar
larvae of brown planthopper (Nilaparvata lugens) were
25 released. After additional 6 days, the number of the 262
surviving insects was examined, and the mortality was
calculated by the following equation.
Mortality (%) = {1- the number of the surviving
insects/20} x 100
5 [0318]
The results of the test that was done according to the
Test example 4 are shown below.
When the prescribed concentration was 200 ppm, each of
the below-mentioned Present compounds showed 90% or greater
10 as the mortality of insects.
Present compound number: 2, 4, 5, 6, 7, 8, 10, 11, 12, 13,
14, 18, and 24
[0319]
Test example 5
15 The test compounds are made to a formulation according
to a similar method to that described in the Formulation
Example 5, and thereto is added water to prepare a diluted
solution containing a prescribed concentration of the test
compound.
20 In the polyethylene cup, 7.7 g of Insecta LF
(manufactured by NOSAN CORPORATION), an artificial diet was
placed, and thereto is irrigated 2 mL of the diluted
solution. Five(5) heads of fourth instar larvae of tobacco
cutworm (Spodoptera litura) are released onto the
25 artificial diet, and the cup was sealed with a lid. After
/ n n 1 /I 1 1 \ .nI I 263
5 days, the number of the surviving tobacco cutworm
(Spodoptela litura) was examined, and the mortality was
calculated by the following equation.
Mortality (%) = {1- the number of the surviving
5 insects/5} x 100 [0320] The results of the test that was done according to the
Test example 5 are shown below.
When the prescribed concentration was 500 ppm, each of
10 the below-mentioned Present compounds showed 80% or greater
as the mortality of insects.
Present compound number: 1, 2, 3, 4, 5, 6, 12, 13, 15, and
18 [0321] 15 Test example 6
The test compounds are made to a formulation according
to a similar method to that described in the Formulation
Example 5, and thereto is added water containing 0.03 v/v %
of a spreader to prepare a diluted solution containing a
20 prescribed concentration of the test compound.
The diluted solutions are sprayed into the cabbage
(Brassicae oleracea) seedling (on the developmental stage
of the second to third true leaf) that is planted in the
polyethylene cup in a ratio of 20 mL/seedling. Thereafter,
25 the stem and leaf thereof was cut out and then is installed
into the polyethylene cup that is covered with the filter
/ n n 1 /I 1 1 \ .nI I 264
paper. Five heads of cabbage moth (Plutella xylostella) at
the second instar larval stages were released into the cup
and the cup was covered with the lid. After 5 days, the
surviving insects were counted, and the mortality of
5 insects was calculated by the following equation.
Mortality (%) = {1- the number of the surviving
insects/5} x 100
[0322]
The results of the test that was done according to the
10 Test example 6 are shown below.
When the prescribed concentration was 500 ppm, each of
the below-mentioned Present compounds showed 80% or greater
as the mortality of insects.
Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11,
15 12, 13, 14, 15, 16, 18, 19, 21, and 24
[0323]
Test example 7
The test compounds are made to a formulation according
to a similar method to that described in the Formulation
20 Example 5, and thereto is added water containing 0.03 v/v %
of a spreader to prepare a diluted solution containing a
prescribed concentration of the test compound. The diluted
solutions are sprayed into the cabbage seedling (on the
developmental stage of the third to fourth true leaf) that
25 is planted in the polyethylene cup in a ratio of 20
/ n n 1 /I 1 1 \ .nI I 265
mL/seedling. Thereafter, 10 heads of cabbage moth
(Plutella xylostella) at the third instar larval stages
were released into the cup, and the insects are held in the
polyethylene cup that was covered with a net. After 5 days,
5 the surviving insects are counted, and the mortality of
insects was calculated by the following equation.
Mortality (%) = {1- the number of the surviving
insects/10} x 100
[0324]
10 The results of the test that was done according to the
Test example 7 are shown below.
When the prescribed concentration was 200 ppm, each of
the below-mentioned Present compounds showed 90% or greater
as the mortality of insects.
15 Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11,
12, 13, 14, 15, 16, 18, 19, and 24
[0325]
Test example 8
The test compounds are dissolved into a mixed solution
20 of polyoxyethylene sorbitan mono-cocoate and acetone
(acetone and polyoxyethylene sorbitan mono-cocoate = 5 : 95
(v/v ratio)) in a ratio of 50 pL of the mixed solution per
1 mg of the test compound. Thereto is added water
containing 0.03 % by volume of a spreader to prepare a
25 diluted solution containing a prescribed concentration of
/ n n 1 /I 1 1 \ .nI I 266
the test compound. Corns (Zea mays) are sown on a tray
overlaid with damped KimWipes (registered trademark).
After corns were grown for 5 days, the entire seedling of
the corn is immersed into the diluted solution for 30
5 seconds. Thereafter, each two grains of the seedling are
installed in a plastic petri dish (90 mm radius), and 10
heads of western corn rootworm (Diabrotica virgifera
virgifera) at the second instar larval stages are released
onto the cup and the cup is covered with a lid. After 5
10 days, the number of the died insects is counted and the
mortality of insects is calculated by the following
equation.
Mortality (%) = {1- the number of the surviving
insects/10} x 100
15 [0326]
The results of the test that was done according to the
Test example 8 are shown below.
When the prescribed concentration was 500 ppm, each of
the below-mentioned Present compounds showed 80% or greater
20 as the mortality of insects.
Present compound number: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12,
14, 16, and 18
[0327]
Test example 9
25 The test compounds are dissolved into a mixed solution
/ n 1 /I 1 1 \ .nI I 267
of xylene, DMF and surfactants (xylene, DMF and surfactants
= 4 : 4 : 1 (v/v ratio)) in a ratio of 10 pL of the mixed
solution per 1 mg of the test compound. Thereto is added
water containing 0.03 % by volume of a spreader to prepare
5 a diluted solution containing a prescribed concentration of
the test compound. The diluted solutions are sprayed into
the cucumber seedling (on the developmental stage of the
second to third true leaf) that is planted in the
polyethylene cup in a ratio of 10 mL/seedling. Thereafter,
10 the second leaf is cut out, and then installed into the
polyethylene cup, and ten heads of cucurbit leaf beetle
(Aulacophora femoralis) at the second instar larval stages
were released into the cup and the cup was covered with the
lid. After 5 days, the number of died insects is counted
15 and the mortality of insects is calculated by the following
equation.
Mortality of insects (%) = (Number of dead insects/10)
X 100
[0328]
20 The results of the test that was done according to the
Test example 9 are shown below.
When the prescribed concentration was 50 ppm, each the
below-mentioned Present compounds showed 80% or greater as
the mortality of insects.
25 Present compound number: 2 and 3
/ n n 1 /I 1 1 \ .nI I 268
[03291
Test example 10
The test compounds are made to a formulation according
to a similar method to that described in the Formulation
5 Example 5, and thereto is added water to prepare a diluted
solution containing a prescribed concentration of the test
compound.
The bottom of the polyethylene cup having 5.5 cm
diameter is matted with the same size of a filter paper,
10 and 0.7 mL of the diluted solution is added dropwise to the
filter paper, and 30 mg sucrose as bait is placed in the
cup uniformly. Ten (10) heads of female adult housefly
(Musca domestic) are released into the polyethylene cup,
and the cup was covered with the lid. After 24 hours, the
15 life and death of housefly is examined and the number of
died insects is counted and the mortality of insects is
calculated by the following equation.
Mortality of insects (%) = (Number of dead
insects/Number of test insects) x 100
20 [03301
The results of the test that was done according to the
Test example 10 are shown below.
When the prescribed concentration was 500 ppm, each
the below-mentioned Present compounds showed 100% as the
25 mortality of insects.
/ n n 1 /I 1 1 \ .nI I 269
Present compound number: 4, 5, and 6
[0331]
Next, Test Examples are used to show an efficacy of
the present composition on controlling harmful arthropods.
5 [0332]
Test example 11
Each 1 mg of the Present compound is dissolved into a
10 pL of the mixed solution of xylene, DMF and surfactants
(xylene, DMF and surfactants = 4 : 4 : 1 (v/v ratio)).
10 Thereto is added water containing 0.02 % by volume of a
spreader to prepare a diluted solution containing a
prescribed concentration of the Present compound.
When the commercially available formulation of the
present active ingredient is used, each of the commercially
15 available formulation is diluted with water containing 0.02
v/v % of the spreader to prepare the prescribed
concentration of the diluted solution of the present active
ingredient.
Whereas, when the commercially available formulation
20 of the present active ingredient is not used, each 1 mg of
the present active ingredient is dissolved into a 10 pL of
the mixed solution of xylene, DMF and surfactants (xylene,
DMF and surfactants = 4 : 4 : 1 (v/v ratio)). Thereto is
added water containing 0.02 % by volume of a spreader to
/ n n 1 /I 1 1 \ .nI I 270
prepare a diluted solution containing a prescribed
concentration of the present active ingredient.
The above prepared diluted solution of the Present
compound and the above prepared diluted solution of the
5 present active ingredient are mixed to prepare the test
chemical solution of the composition comprising the Present
compound and the present active ingredient.
A leaf disk (length 1.5 cm) of the seed leaf of
cucumber (Cucumis sativus) is placed into each well in a 24
10 well microplate, and 2 wingless adults of a cotton aphid
(Aphis gossypii) and 8 nymphs of a cotton aphid are
released per 1 well, and the test chemical solution is
sprayed in a ratio of 20 pL per 1 well, which is referred
to as a treated group.
15 Whereas, 20 pL water containing 0.02 v/v % of the
spreader is sprayed into a well instead of the test
chemical solution, which is referred to as an untreated
group.
After the test chemical solution is dried, the upper
20 part of a microplate is covered with the gas permeable film
sheet (Product Name: AeraSal, manufactured by Excel
Scientific Inc.), and 5 days after the release, the number
of the surviving insects of each well is examined.
The controlling value is calculated by the following
25 equation. 271
Controlling value (%) = {l-(Tai)/(Cai)}x100
wherein the symbols in the formula represent the following
descriptions.
Cai: Number of the surviving insects at the time of
5 the investigation in untreated group;
Tai: Number of the surviving insects at the time of
the investigation in treated group;
[03331
The composition that is examined according to a method
10 of Test example 11 is shown in Table 47. As a result, the
composition described in Table 47 show an excellent
efficacy on controlling harmful arthropods.
[0334] Table 47 15 [Table 47]
Concentration (ppm) (Present Composition compound + Present active
______ingredient) any one kind of Present compounds 1 ± Clothianidin 200 + 2000 to 348 any one kind of Present compounds 1 + Clothianidin 200 + 200 to 348 any one kind of Present compounds 1 + Clothianidin 500 + 50 to 348 any one kind of Present compounds 1 + Thiamethoxam 200 + 2000 to 348 272 any one kind of Present compounds 1 + Thiamethoxam 200 + 200 any one kind of Present compounds 1 + Thiamethoxam 500 + 50 to 348 any one kind of Present compounds 1 + Imidacloprid 200 + 2000 to 348 any one kind of Present compounds 1 + Imidacloprid 200 + 200 to 348 any one kind of Present compounds 1 + Imidacloprid 500 + 50 to 348 any one kind of Present compounds 1 + Thiacloprid 200 + 2000 to 348 any one kind of Present compounds 1 + Thiacloprid 200 + 200 to 348 any one kind of Present compounds 1 + Thiacloprid 500 t 50 to 348 any one kind of Flupyradifuro Present compounds 1 + 200 + 2000 to 348ne any one kind of Flupyradifuro; Present compounds 1 + 200 + 200 ne to 348 n any one kind of Flupyradifuro Present compounds 1 + l500 + 50 ne to 348 [0335]
Table 47 (Continued)
[Table 48] Concentration (ppm) (Present Composition compound + Present active ingredient) any _one kind of + Sulfoxaflor 200 + 2000 273
Present compounds 1 to 348 any one kind of Present compounds 1 + Sulfoxaflor 200 + 200 to 348 any one kind of Present compounds 1 + Sulfoxaflor 500 + 50 to 348 any one kind of Present compounds 1 + Triflumezopyrim 200 + 2000 to 348 any one kind of Present compounds 1 + Triflumezopyrim 200 + 200 to 348 any one kind of Present compounds I + Triflumezopyrim 500 + 50 to 348 any one kind of Present compounds 1 + Dicloromezotiaz 200 + 2000 to 348 any one kind of Present compounds 1 + Dicloromezotiaz 200 + 200 to 348 any one kind of Present compounds 1 + Dicloromezotiaz 500 + 50 to 348 any one kind of Present compounds I + Beta-cyfluthrin 200 + 2000 to 348 any one kind of Present compounds 1 + Beta-cyfluthrin 200 + 200 to 348 any one kind of Present compounds 1 + Beta-cyfluthrin 500 + 50 to 348 any one kind of Present compounds 1 + Tefiuthrin 200 + 2000 to 348 any one kind of Present compounds 1 + Tefluthrin 200 + 200 to 348 any one kind of Present compounds 1 + Tefluthrin 500 + 50 to 348 [0336] 274
Table 47 (Continued)
[Table 49] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of Present compounds 1 + Fipronil 200 + 2000 to 348 any one kind of Present compounds 1 + Fipronil 200 + 200 to 348 any one kind of Present compounds 1 + Fipronil 500 + 50 to 348 any one kind of Present compounds 1 + Chlorantraniliprole 200 + 2000 to 348 any one kind of Present compounds 1 + Chlorantraniliprole 200 + 200 to 348 any one kind of Present compounds 1 + Chlorantraniliprole 500 + 50 to 348 any one kind of + Present compounds 1 Cyantraniliprole 200 + 2000 to 348 any one kind of + Present compounds 1 Cyantraniliprole 200 + 200 any one kind of + Present compounds 1 Cyantraniliprole 500 + 50 to 348
Present compounds 1 Tetraniliprole 200 + 2000 any one kind of + Present compounds 1 Tetraniliprole 200 + 200 to 348 any one kind of + to 348 Present compounds 1 Tetraniliprole 500 + 50 275
any one kind of + Present compounds 1 Thiodicarb 200 + 2000 to 348 any one kind of + Present compounds 1 Thiodicarb 200 + 200 to 348 any one kind of + Present compounds 1 Thiodicarb 500 + 50 to 348 [0337]
Table 47 (Continued)
[Table 50] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Carbofuran 200 + 2000 to 348 any one kind of + Present compounds 1 Carbofuran 200 + 200 to 348 any one kind of + Present compounds 1 Carbofuran 500 + 50 to 348 any one kind of + Present compounds 1 fluxametamide 200 + 2000 to 348 any one kind of + Present compounds 1 fluxametamide 200 + 200 to 348 any one kind of + Present compounds 1 fluxametamide 500 + 50 to 348 any one kind of + Present compounds 1 Afoxolaner 200 + 2000 to 348 any one kind of + Present compounds 1 Afoxolaner 200 + 200 to 348 any one kind of + Afoxolaner 500 + 50 276
Present compounds 1 to 348 any one kind of + Present compounds 1 fluralaner 200 ± 2000 to 348 any one kind of + Present compounds 1 fluralaner 200 ± 200 to 348 any one kind of + Present compounds 1 fluralaner 500 ± 50 to 348 any one kind of + Present compounds 1 broflanilide 200 ± 2000 to 348 any one kind of + Present compounds 1 broflanilide 200 ± 200 to 348 any one kind of + Present compounds 1 broflanilide 500 ± 50 to 348 [03381 Table 47 (Continued) [Table 51]
Concentration (ppm) (Present Composition compound + Present active _ingredient) any one kind of + Present compounds 1 Abamectin 200 + 2000 to 348 any one kind of + Present compounds 1 Abamectin 200 ± 200 to 348 any one kind of + Present compounds 1 Abamectin 500 ± 5 to 348 any one kind of + Present compounds 1 Fluopyram 200 ± 2000 to 348 any one kind of + Present compounds 1 Fluopyram 200 ± 20 to 348 277
to 348 any one kind of + Present compounds 1 Fluopyram 500 + 0.5 to 348 any one kind of + Present compounds I Fluensulfone 200 + 2000 to 348 any one kind of + Present compounds 1 Fluensulfone 200 + 200 to 348 any one kind of + Present compounds 1 Fluensulfone 500 + 5 to 348 any one kind of + Present compounds 1 Fluazaindolizine 200 + 2000 to 348 any one kind of + Present compounds 1 Fluazaindolizine 200 + 200 to 348 any one kind of + Present compounds 1 Fluazaindolizine 500 + 5 to 348 any one kind of + Present compounds 1 Tioxazafen 200 + 2000 to 348 any one kind of + Present compounds 1 Tioxazafen 200 + 200 to 348 any one kind of + Present compounds 1 Tioxazafen :500 + 5
[0339]
Table 47 (Continued)
[Table 52]
Concentration (ppm) (Present Composition compound + Present active :ingredient) any one kind of + Insecticide P200 + 2p0 Peent copoud compouda 278
to 348 any one kind of + Insecticide Present compounds 1 compound al :2 00 + 200 to 318 any one kind of + Insecticide Present compounds 1 2o00 + 20 compound al any one kind of + to 348 Present compounds 1 Mycorrhizal fungi 200 + 200 any one kind of + to 348 Present compounds 1 Mycorrhizal fungi :200 + 200 to 348 any one kind of + Present compounds 1 BacirrhizaMycorrhizal frmus fungi :500:200 + 20005
kind of + anyto 318one Present compounds 1 Bacillus firmus 200 + 2000
+ toany 348one kind of Present compounds I Bacillus firmus 200 + 200
of + toany 348one kind Present compounds 1 Bacillus firms 500 + 5 to 348 . any one kind of + Bacillus Present compounds 1 , 200 + 2000 amyloliquefaciens
kind of + any one Bacillus Present compounds 1 .n200+ 200 amyloliquefaciens to 348 any one kind of + , Present compounds 1 ;s500 + 2 amyloliquefaciens. to 348 any one kind of + Present compounds 1 Pasteuria nishizawae :200 + 2000
[0340]
Table 47 (Continued) 279
{Table 531 Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + i Pasteuria Present compounds 1 200 + 2000 to 348 penetrans any one kind of + . Pasteuria Present compounds 1 :200 + 200 to 348 penetrans any one kind of + Present compounds 1 500 + 5 to 348 penetrans
Present compounds 1 Tebuconazole 200 + 2000 to 348 any one kind of + Present compounds 1 Tebuconazole 200 + 20 to 348 any one kind of + Present compounds 1 Tebuconazole 500 + 0.5 to 348 any one kind of + Present compounds 1 Prothioconazole 200 + 2000 any one kind of + to 348
Present compounds I Prothioconazole 200 + 20 to 348 any one kind of + Present compounds 1 Prothioconazole 500 + 0.5 to 348 any one kind of + Present compounds 1 Metconazole 200 + 2000 to 348 any one kind of + Present compounds 1 Metconazoie 200 + 20 any one kind of+ to 348
Present compounds 1 Metconazole 500 + 0.5 to 348 any one kind of + Ipconazole 2 00 + 2 00.0 280
Present compounds 1 to 348 any one kind of + Present compounds 1 Ipconazole 200 + 20 to 348 any one kind of + Present compounds 1 Ipconazole 500 + 0.5 to 348
[0341]
Table 47 (Continued)
[Table 54] IConcentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Triticonazole 200 + 2000 to 348 any one kind of + Present compounds 1 Triticonazole 200 + 20 to 348 any one kind of + Present compounds 1 Triticonazole 500 + 0.5 to 348 any one kind of + Present compounds 1 Difenoconazole 200 + 2000 to 348 any one kind of + Present compounds 1 Difenoconazole 200 + 20
any one kind of + Present compounds 1 Difenoconazole 500 + 0.5 to 348 any one kind of + Present compounds 1 Imazalil 200 + 2000 to 348 any one kind of + Present compounds 1 Imazalil 200 + 20 to 348 any one kind of + Imazalil :500 + 0.5 281
Present compounds 1 to 348 any one kind of + Present compounds 1 Triadimenol 200 + 2000 to 348 any one kind of + Present compounds 1 Triadimenol 200 + 20 to 348 any one kind of + Present compounds I Triadimenol 500 + 0.5 to 348 any one kind of + Present compounds 1 Tetraconazole 200 + 2000 to 348 any one kind of + Present compounds 1 Tetraconazole 200 + 20 to 348 any one kind of + Present compounds 1 Tetraconazole 500 + 0.5 to 348 [0342]
Table 47 (Continued)
[Table 55] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Flutriafol 200 + 2000 to 348 any one kind of + Present compounds 1 Flutriafol 200 + 20 to 348 any one kind of + Present compounds 1 Flutriafol 500 + 0.5 to 348 any one kind of + Present compounds 1 Mandestrobin 200 + 2000 to 348 any one kind of + Mandestrobin 200 + 20 282
Present compounds 1 to 348 any one kind of + Present compounds 1 Mandestrobin 500 + 0.5 to 348 any one kind of + Present compounds 1 Azoxystrobin 200 + 2000 to 348 any one kind of + Present compounds 1 Azoxystrobin 200 + 20 to 348 any one kind of + Present compounds 1 Azoxystrobin 500 + 0.5 to 348 any one kind of + Present compounds 1 Pyraclostrobin 200 + 2000 to 348 any one kind of + Present compounds 1 Pyraclostrobin 200 + 20 to 348 any one kind of + Present compounds 1 Pyraclostrobin 500 + 0.5 to 348 any one kind of + Present compounds 1 Trifloxystrobin 200 + 2000 to 348 any one kind of + Present compounds 1 Trifloxystrobin 200 + 20 to 348 any one kind of + Present compounds 1 Trifloxystrobin 500 + 0.5 to 348 £0343]
Table 47 (Continued)
[Table 56] Concentration (ppm) (Present Composition compound + Present active :ingredient) any one kind of + Fluoxastrobin 200 + 2000 283
Present compounds 1 to 348 any one kind of + Present compounds 1 Fluoxastrobin 200 + 20 to 348 any one kind of + Present compounds 1 Fluoxastrobin 500 + 0.5 to 348 any one kind of + Present compounds 1 Picoxystrobin 200 + 2000 to 348 any one kind of + Present compounds 1 Picoxystrobin 200 + 20 to 348 any one kind of + Present compounds 1 Picoxystrobin 500 + 0.5 to 348 any one kind of + Present compounds 1 Fenamidone 200 + 2000 to 348 any one kind of + Present compounds 1 Fenamidone 200 + 20 to 348 ...... ------...... ------...... any one kind of + Present compounds 1 Fenamidone 500 + 0.5 to 348 any one kind of + Present compounds 1 Metalaxyl 200 + 2000 to 348 any one kind of + Present compounds 1 Metalaxyl 200 + 20 to 348 any one kind of + Present compounds 1 Metalaxyl 500 + 0.5 to 348
any one kind of -+ Present compounds 1 Metalaxyl M 200 + 2000 to 348 any one kind of + Present compounds 1 Metalaxyl M 200 + 20 to 348 any one kind of + Present compounds 1 Metalaxyl M 500 + 0.5 to 348 [0344] 284
Table 47 (Continued)
(Table 57] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Fludioxonil 200 + 2000 to 348 any one kind of + Present compounds 1 Fludioxonil 200 + 20 to 348 any one kind of + Present compounds 1 Fludioxonil 500 + 0.5 to 348 any one kind of + Present compounds 1 Sedaxane 200 + 2000 to 348 any one kind of + Present compounds 1 Sedaxane 200 + 20 to 348 any one kind of + Present compounds 1 Sedaxane 500 + 0.5 t o 3 4 8 ...... ------...... - -- any one kind of + Present compounds 1 Penfurufen 200 + 2000 to 348 any one kind of + Present compounds 1 Penfurufen 200 + 20 any one kind of + Present compounds 1 Penfurufen 500 + 0.5 to 348 any one kind of + Present compounds 1 Fluxapyroxad 200 + 2000 any one kind of + Present compounds 1 Fluxapyroxad 200 + 20 to 348 any one kind of + Fluxapyroxad 500 + 0.5 Present compounds 1 285
to 348 any one kind of + Present compounds 1 Benzovindiflupyr 200 + 2000 to 348 any one kind of + Present compounds 1 Benzovindiflupyr 200 + 20 to 348 any one kind of + Present compounds 1 Benzovindiflupyr 500 + 0.5 to 348 [0345]
Table 47 (Continued)
[Table 58] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Boscalid 200 + 2000 to 348 any one kind of + Present compounds 1 Boscalid 200 + 20 to 348 any one kind of + Present compounds I Boscalid 500 + 0.5 to 348 any one kind of + Present compounds 1 Carboxin 200 + 2000 to 348 any one kind of + Present compounds 1 Carboxin 200 + 20 to 348 any one kind of + Present compounds I Carboxin 500 + 0.5 to 348 any one kind of + Present compounds 1 Penthiopyrad 200 + 2000 to 348 any one kind of + Present compounds 1 Penthiopyrad 200 + 20 to 348 286
any one kind of + Present compounds 1 Penthiopyrad 500 + 0.5 to 348 any one kind of + Present compounds 1 Flutolanil 200 + 2000 to 348 any one kind of + Present compounds 1 Flutolanil 200 + 20 to 348 any one kind of + Present compounds 1 Flutolanil 500 + 0.5
any one kind of + Present compounds 1 Captan 200 + 2000 to 348 any one kind of + Present compounds 1 Captan 200 + 20 to 348 any one kind of + Present compounds 1 Captan 500 + 0.5 to 348
[0346]
Table 47 (Continued)
[Table 59] Concentration (ppm) (Present Composition compound + Present active ingredient) any one kind of + Present compounds 1 Thiuram 200 + 2000 to 348 any one kind of + Present compounds 1 Thiuram 200 + 20 t o 3 4 8 ...... ------any one kind of + Present compounds 1 Thiuram 500 + 0.5 to 348 any one kind of + Tolclofos Present compounds 1 200 + 2000 methyl _t o 3 8...... -- -- 287
any one kind of + Present compounds 1 Tolciofos- 200 + 20 to 348 methyl any one kind of + Tolclofos Present compounds 1 500 + 0.5 to 348 methyl any one kind of + Present compounds 1 Thiabendazole 200 + 2000 to 348 any one kind of + Present compounds 1 Thiabendazole 200 + 20 to 348 any one kind of + Present compounds 1 Thiabendazole 500 + 0.5 to 348 any one kind of + Present compounds 1 Ethaboxam 200 + 2000 to 348
any one kind of + Present compounds 1 Ethaboxam 500 + 0.5 to 348 any one kind of + Present compounds 1 Mancozeb 200 + 2000 to 348 any one kind of + Present compounds 1 Mancozeb 200 + 20 any one kind of + to 348
Present compounds 1 Mancozeb 500 + 0.5 to 348 [0347)
Table 47 (Continued)
[Table 60]
Concentration (ppm) (Present Composition compound + Present active ingredient) 288 any one kind of + Present compounds 1 Picarbutrazox 200 + 2000 to 348 any one kind of + Present compounds 1 Picarbutrazox 200 + 20 to 348 any one kind of + Present compounds 1 Picarbutrazox 500 + 0.5 to 348 any one kind of + Present compounds 1 Oxathiapiprolin 200 + 2000 to 348 any one kind of + Present compounds 1 Oxathiapiprolin 200 + 20 to 348 any one kind of + Present compounds 1 Oxathiapiprolin 500 + 0.5 to 348 any one kind of + Present compounds 1 Silthiofam 200 + 2000 t o 3 48...... ------any one kind of + Present compounds 1 Silthiofam 200 + 20 to 348 any one kind of + Present compounds 1 Silthiofam 500 + 0.5 to 348 any one kind of + Fungicide Present compounds 1 200 + 2000 compound pl kind of + Fg. toany 348one Fungicide Present compounds 1 200 + 20 compound D1
Fungicide Present compounds 1 compound + 0.5 to 348 one kind of + any Fungicide Present compounds 1 200 + 2000 compound P2 to_343any one kind of + Fungicide Present compounds 1 200 + 20 compound 2 any one kind of+ Fungicide Present compounds 1 500 + 0.5 compound P2 to 348
[0348] 289
Next, the Test example is used to show an efficacy of
the present composition on controlling harmful arthropods.
[0349]
Test example 12
5 Each 1 mg of the Present compound was dissolved into a
10 pL of the mixed solution of xylene: DMF : surfactants
(Trade name: Sorpol 3005X, manufactured by TOHO CHEMICAL
INDUSTRY CO.LTD) (xylene : DMF : surfactants = 4 : 4 : 1
(v/v ratio)). Thereto was added water containing 0.02 %
10 (v/v) of the spreading agent (Trade name: Sindain,
manufactured by Sumitomo Chemical Company, Limited) so as
to give a diluted solution containing the prescribed
concentration of the Present compound.
When the commercially available formulation of the
15 present active ingredient was used, each of the
commercially available formulation was diluted with water
containing 0.02 v/v % of the spreader to prepare the
prescribed concentration of the diluted solution of the
present active ingredient.
20 Whereas, when the commercially available formulation
of the present active ingredient was not used, each 1 mg of
the present active ingredient was dissolved into a 10 pL of
the mixed solution of xylene, DMF and surfactants (xylene,
DMF and surfactants = 4 : 4 : 1 (v/v ratio)). Thereto was
25 added water containing 0.02 % by volume of a spreader 290
(Trade name: Sindain, manufactured by Sumitomo Chemical
Company, Limited) to prepare a diluted solution containing
a prescribed concentration of the present active ingredient.
The above prepared diluted solution of the Present
5 compound and the above prepared diluted solution of the
present active ingredient were mixed to prepare the test
chemical solution of the composition comprising the Present
compound and the present active ingredient.
A leaf disk (length 1.5 cm) of the seed leaf of
10 cucumber (Cucumis sativus) was placed into each well in a
24 well microplate, and 2 wingless adults of a cotton aphid
(Aphis gossypii) and 8 nymphs were released per 1 well, and
the test chemical solution was sprayed in a ratio of 20 pL
per 1 well, which is referred to as a treated group.
15 Whereas, 20 pL of water containing 0.02 v/v % of the
spreader (Trade name: Sindain, manufactured by Sumitomo
Chemical Company, Limited) was sprayed into a well instead
of the test drug solution, which was referred to as an
untreated group.
20 After the test chemical solution was dried, the upper
part of a microplate was covered with the gas permeable
film sheet (Product Name: AeraSeal, manufactured by Excel
Scientific Inc.), and 5 days after the release, the number
of the surviving insects of each well was examined.
25 The controlling value was calculated by the following
/ n 1 /I 1 1 \ .nI I 291
equation.
Controlling value (%) = {l-(Tai)/(Cai)}x100
wherein the symbols in the formula represent the following
descriptions.
5 Cai: Number of the surviving insects at the time of
the investigation in untreated group;
Tai: Number of the surviving insects at the time of
the investigation in treated group;
[0350)
10 The result of the test that was done according to Test
example 12 is shown below.
Any the present composition wherein the respective
concentration of the Present compound and the present
active ingredient is indicated in the following Tables 48
15 to 61 showed 90 % or greater as a controlling value against
harmful arthropods.
[0351]
Table 48
[Table 611
Composition Concentration (ppm) Present compound 2 + Clothianidin 200 + 2000 Present compound 2 + Clothianidin 500 + 50 Present compound 2 + Imidacloprid 200 + 2000 Present compound 2 + Imidacloprid 500 + 50 Present compound 2 + Thiamethoxam 200 + 2000 Present compound 2 + Thiamethoxam 500 + 50 Present compound 2 + Azoxystrobin 200 + 200 Present compound 2 + Azoxystrobin 500 + 0.5 Present compound 2 + Difenoconazole 200 + 200 292
Present compound 2 + Difenoconazole 500 + 0.5 Present compound 2 + Ethaboxam 200 + 200 Present compound 2 + Ethaboxam 500 + 0.5 Present compound 2 + Fludioxonil 200 + 200 Present compound 2 + Fludioxonil 500 + 0.5 Present compound 2 + Fluopyram 200 + 2000 Present compound 2 + Fluopyram 500 + 0.5 Present compound 2 + Fluoxastrobin 200 + 200 Present compound 2 + Fluoxastrobin 500 + 0.5 Present compound 2 + Flutolanil 200 + 200 Present compound 2 + Flutolanil 500 + 0.5 [0352)
Table 48 (Continued)
[Table 62] .m i .Concentration Composition(ppm) Present compound 2 + Flutriafol 200 + 200 Present compound 2 + Flutriafol 500 + 0.5 Present compound 2 + Fluxapyroxad 200 + 200 Present compound 2 + Fluxapyroxad 500 + 0.5 Present compound 2 + Ipconazole 200 + 200 Present compound 2 + Ipconazole 500 + 0.5 Present compound 2 + Mandestrobin 200 + 200 Present compound 2 + Mandestrobin 500 + 0.5 Present compound 2 + Metalaxyl M 200 + 200 Present compound 2 + Metalaxyl M 500 + 0.5 Present compound 2 + Metalaxyl 200 + 200 Present compound 2 + Metalaxyl 500 + 0.5 Present compound 2 + Metconazole 200 + 200 Present compound 2 + Metconazole 500 + 0.5 Present compound 2 + Oxathiapiprolin 200 + 200 Present compound 2 + Oxathiapiprolin 500 + 0.5 Present compound 2 + Penfurufen 200 + 200 Present compound 2 + Penfurufen 500 + 0.5 Present compound 2 + Penthiopyrad 200 + 200 Present compound 2 + Penthiopyrad 500 + 0.5 [0353]
5 Table 48 (Continued)
[Table 63] Concentratio Composition n 293
(ppm)
200 cPound 2 + Picoxystrobin 200 + Present 0.5 compound 2 + Picoxystrobin 500 + Present compond 2 + Prothioconazole 200 + 200 compound Present 2 + Prothioconazole 500 + 0.5 compound Present compond 2 + Pyraclostrobin 200 + 200 compound Present 2 + Pyraclostrobin 500 + 0.5 compound 200 compnd 2 + Fungicide compound P2 200 + Present,, 500 + 0.5 compound 2 + Fungicide compound s2 Present 2 + Sedaxane 200 + compound 200 Present 2 + Sedaxane 500 + 0.5 compound Present 2 + Tebuconazole 200 + 200 compound Present 2 + Tebuconazole 500 + 0.5 compound compond 2 + Triadimenol 200 + 200 compoundPresent5005
2 + Triadimenol 500 + 0.5 compoundPresent
compond 2 + Trifloxystrobin 200 + 200 compoundPresent,,
Presentcompound 2 + Trifloxystrobin 500 + 0.5 Present 2 + Triticonazole 200 + 200 compound Present compond 2 + Triticonazole 500 + 0.5 compound [0354]
Table 49
[Table 64]
Composition Concentration (ppm) Present compound 4 + Clothianidin 200 + 2000 Present compound 4 + Clothianidin 500 + 50 294
Present compound 4 + Imidacloprid 200 + 2000 Present compound 4 + Imidacloprid 500 + 50 Present compound 4 + Thiamethoxam 200 + 2000 Present compound 4 + Thiamethoxam 500 + 50 Present compound 4 + Azoxystrobin 200 + 200 Present compound 4 + Azoxystrobin 500 + 0.5 Present compound 4 + Difenoconazole 200 + 200 Present compound 4 + Difenoconazole 500 + 0.5 Present compound 4 + Ethaboxam 200 + 200 Present compound 4 + Ethaboxam 500 + 0.5 Present compound 4 + Fludioxonil 200 + 200 Present compound 4 + Fludioxonil 500 + 0.5 Present compound 4 + Fluopyram 200 + 2000 Present compound 4 + Fluopyram 500 + 0.5 Present compound 4 + Fluoxastrobin 200 + 200 Present compound 4 + Fluoxastrobin 500 + 0.5 Present compound 4 + Flutolanil 200 + 200 Present compound 4 + Flutolanil 500 + 0.5 [0355]
Table 49 (Continued)
[Table 65) Concentration Composition (ppm) Present compound 4 + Flutriafol 200 + 200 Present compound 4 + Flutriafol 500 + 0.5 Present compound 4 + Fluxapyroxad 200 + 200 Present compound 4 + Fluxapyroxad 500 + 0.5 Present compound 4 + Ipconazole 200 + 200 Present compound 4 + Ipconazole 500 + 0.5 Present compound 4 + Mandestrobin 200 + 200 Present compound 4 + Mandestrobin 500 + 0.5 Present compound 4 + Metalaxyl M 200 + 200 Present compound 4 + Metalaxyl M 500 + 0.5 Present compound 4 + Metalaxyl 200 + 200 Present compound 4 + Metalaxyl 500 + 0.5 Present compound 4 + Metconazole 200 + 200 Present compound 4 + Metconazole 500 + 0.5 Present compound 4 + Oxathiapiprolin 200 ± 200 Present compound 4 + Oxathiapiprolin 500 + 0.5 Present compound 4 + Penfurufen 200 + 200 Present compound 4 + Penfurufen 500 + 0.5 Present compound 4 + Penthiopyrad 200 + 200 Present compound 4 + Penthiopyrad 500 + 0.5 295
[0356]
Table 49 (Continued)
[Table 66] Concentratio Composition n (ppm) Present compound + Picoxystrobin 200 200 compoundPresent compond 4 + Picoxystrobin 500 + 0.5 Present compoundcompond 4 + Prothioconazole 200 + 200 Present 4 + Prothioconazole 500 + 0.5 compound Present 4+ Pyraclostrobin 200 + 200 compound Present compound 4 + Pyraclostrobin 500 + 0.5 Present . . compound 4 + Fungicide compound $2 200 t 200 compoundPresent compound4 ± Fungicide compound 12 500 + 0.5 Present 4 + Sedcaxane 200 + 200 compound compoundPresent 4 + Sedxan 500 + 0. compound
Present 4 + Tebuconazole 200 + 200 Present 4 + Tebuconazole 500 + 0.5 compound compound Present 4 + Triadimenol 200 + 200 Present compond 4 + Triadimenol 500 + 0.5 compound compond 4 + Trifloxystrobin 200 + 200 compondcompound 4 + Trifloxystrobin 500 + 0.5 Present 4+Tiioale200 + 200 compound +Titcnzl Present 4 + Triticonazole 500 + compound 0.5 [0357] 296
Table 50
[Table 67] Concentration Composition(pm (ppm) Present compound 5 + Clothianidin 200 + 2000 Present compound 5 + Clothianidin 500 + 50 Present compound 5 + Imidacloprid 200 + 2000 Present compound 5 + Imidacloprid 500 + 50 Present compound 5 + Thiamethoxam 200 + 2000 Present compound 5 + Thiamethoxam 500 + 50 Present compound 5 + Azoxystrobin 200 + 200 Present compound 5 + Azoxystrobin 500 + 0.5 Present compound 5 + Difenoconazole 200 + 200 Present compound 5 + Difenoconazole 500 + 0.5 Present compound 5 + Ethaboxam 200 + 200 Present compound 5 + Ethaboxam 500 + 0.5 Present compound 5 + Fludioxonil 200 + 200 Present compound 5 + Fludioxonil 500 + 0.5 Present compound 5 + Fluopyram 200 + 2000 Present compound 5 + Fluopyram 500 + 0.5 Present compound 5 + Fluoxastrobin 200 + 200 Present compound 5 + Fluoxastrobin 500 + 0.5 Present compound 5 + Flutolanil 200 + 200 Present compound 5 + Flutolanil 500 + 0.5 [0358]
Table 50 (Continued)
5 [Table 68] Concentration Composition (ppm) Present compound 5 + Flutriafol 200 + 200 Present compound 5 + Flutriafol 500 + 0.5 Present compound 5 + Fluxapyroxad 200 + 200 Present compound 5 + Fluxapyroxad 500 + 0.5 Present compound 5 + Ipconazole 200 + 200 Present compound 5 + Ipconazole 500 + 0 5 Present compound 5 + Mandestrobin 200 + 200 Present compound 5 + Mandestrobin 500 + 0.5 Present compound 5 + Metalaxyl M 200 + 200 Present compound 5 + Metalaxyl M 500 + 0.5 Present compound 5 + Metalaxyl 200 + 200 Present compound 5 + Metalaxyl 500 + 0.5 Present compound 5 + Metconazole 200 + 200 297
Present compound 5 + Metconazole 500 + 0.5 Present compound 5 + Oxathiapiprolin 200 + 200 Present compound S + Oxathiapiprolin 500 + 0.5 Present compound 5 + Penfurufen 200 + 200 Present compound 5 + Penfurufen 500 + 0.5 Present compound 5 + Penthiopyrad 200 + 200 Present compound 5 + Penthiopyrad 500 + 0.5 [0359]
Table 50 (Continued)
[Table 69)
Composition Concentration (ppm) Present compound 5 + Picoxystrobin 200 + 200 Present compond 5 + Picoxystrobin 500 + 0.5 compound Present 5 + Prothioconazole 200 + 200 compound Present s+ Prothioconazole 500 + 0.5 compound Present 5 + Pyraclostrobin 200 + 200 compound Present compound 5 + Pyraciostrobin 500 + 0.5 Present. compond 5 + Fungicide compound P2 200 + 200 compound Present.. compond 5 + Fungicide compound 32 500 + 0.5 compound Present compond 5 + Sedaxane 200 + 200 compound Present Sedaxane 5 + 500 + 0.5 compound Present compond 5 + Tebuconazole 200 + 200 compound Present 5 + Tebuconazole 500 + 0.5 compound Present compond 5 + Triadimenol 200 + 200 compound Present. compond 5 + Triadimenol 500 + 0.5 compound 5 + Trifloxystrobin 200 + 200 Present 5 + Trifloxystrobin 500 + 0.5 compound 298
Present 5 + Triticonazole 200 + 200 compound Present 5 + Triticonazole 500 + 0.5 compound
[0360]
Table 51
[Table 70]
.m i .Concentration Composition(pm (ppm) Preond 6 + Clothianidin 200 + 2000 compound Present 6 + Clothianidin 500 + 50 compound Present 6 + Imidacloprid 200 + 2000 compound Present 6 + Imidacloprid 500 + 50 compound Present 6 + Thiamethoxam 200 + 2000 compound Present 6 + Thiamethoxam 500 + 50 compound Present 6 + Azoxystrobin 200 + 200 compound Present 6 + Azoxystrobin 500 + 0.5 compound Present 6 + Difenoconazole 200 + 200 compound Present 6 + Difenoconazole 500 + 0.5 compound Present 6 + Ethaboxam 200 + 200 compound Present 6 + Ethaboxam 500 + 0.5 compound Present 6 + Fludioxonil 200 + 200 compound Present 6 + Fludioxonil 500 + 0.5 compound Present 6 + Fluopyram 200 + 2000 compound Present 6 + Fluopyram 500 + 0.5 compound Present 6 + Fluoxastrobin 200 + 200 compound 500 0.5 5 -reent 6 + Fluoxastrobin + 299
compound Present 6 + Flutolanil 200 + 200 compound Present 6 + Flutolanil 500 + 0.5 compound
103611
Table 51 (Continued)
[Table 71]
Composition Concentration (ppm) Present 6 + Flutriafol 200 + 200 compound Present 6 + Flutriafol 500 + 0.5 compound Present compond 6 + Fluxapyroxad 200 + 200 compound Present compound 6 + Fluxapyroxad 500 + 0.5 Present + 200 compound 6 + Ipconazole 200 Present compond 6 + Ipconazole 500 + 0.5 compound Present + Mandestrobin 200 + 200 compound Present 6 + Mandestrobin 500 + 0.5 compound Present 6 + Metalaxyl M 200 + 200 compound Present 6 + Metalaxyl M 500 + 0.5 compound Present 6 + Metalaxyl 200 + 200 compound Present 6 + Metalaxyl 500 + 0.5 compound Present compond 6 + Metconazole 200 + 200 compound Present compond 6 + Metconazole 500 + 0.5 compound coesed 6 + Oxathiapiprolin + 200 Present 200 compond 6 + Oxathiapiprolin 200 + 005 compound 6 + Oxathiapiprolin 500 + Present compond 6 + Penfurufen 200 + 200 compound 300
Present 6 + Penfurufen 500 + 0.5 compound Present 6 + Penthiopyrad 200 + 200 compound Present 6 + Penthiopyrad 500 + 0.5 compound [0362)
Table 51 (Continued)
[Table 72]
Composition concentration (ppm) Present 6 + Picoxystrobin 200 + 200 compound Present 6 + Picoxystrobin 500 + 0.5 compound Present 6 + Prothioconazole 200 + 200 compound Present 6 + Prothioconazole 500 + 0.5 compound Present 6 + Pyraclostrobin 200 + 200 compound Present 6 + Pyraclostrobin 500 + 0.5 compound Present 6 + Fungicide compound 200 + 200 compound p2 Present 6 + Fungicide compound 500 + 0.5 compound 6 2 Present 6 + Sedaxane 200 + 200 compound Present 6 + Sedaxane 500 + 0.5 compound Present 6 + Tebuconazole 200 + 200 compound Present 6 + Tebuconazole 500 + 0.5 compound Present 6 + Triadimenol 200 + 200 compound Present 6 + Triadimenol 500 + 0.5 compound Present 6 + Trifloxystrobin 200 + 200 compound Present 6 + Trifloxystrobin 500 + 0.5 compound 6o5 Present 6 + Triticonazole 200 + 200 301
compound
Present6 + Triticonazole 500 + 0.5 compound [0363]
Table 52
[Table 73)
Composition Concentration (ppm) Present 7 + Clothianidin 200 + 2000 compound Present compound 7 + Clothianidin 500 + 50 compound compond 7 + Imidacloprid 200 + 2000 compound Present compond 7 + Imidacloprid 500 + 50 compound Present 7 + Thiamethoxam 200 + 2000 compound Present compond 7 + Thiamethoxam 500 + 50 compound Present compond 7 + Azoxystrobin 200 + 200 compound compond 7 + Azoxystrobin 500 + 0.5 compound Present 7 + Difenoconazole 200 + 200 compound Present compond 7 + Difenoconazole 500 + 0.5 compound Present 7 + Ethaboxam 200 + 200 compound Preent7 + Ethaboxam 500 + 0.5 compoundPresent20 Present 7 + Fludioxonil 200 + 200 compound Present 7 + Fludioxonil 500 + 0.5 compound
compond 7 + Fluopyram 200 + 2000 compoundPresent Present 200 + 0.00 compound7+Floya50 Present 7 + Fluoxastrobin 200 + 200 compound Present 7 + Fluoxastrobin 500 + 0.5 compound 302
Present 7 + Flutolanil 200 + 200 compound Present 7 + Flutolanil 50o0 + 0. 5 compound [0364]
Table 52 (Continued)
[Table 74]
Composition Concentration ______(ppm) Present 7 + Flutriafol 200 + 200 compound Present 7 + Flutriafol 500 + 0.5 compound Present 7 + Fluxapyroxad 200 + 200 compound Present 7 + Fluxapyroxad 500 + 0.5 compound Present -7 + Ipconazole 200 + 200 compound Present 7 + Ipconazole 500 + 0.5 compound Present 7 + Mandestrobin 200 + 200 compound Present 7 + Mandestrobin 500 + 0.5 compound Present 7 + Metalaxyl M 200 + 200 compound Present 7 + Metalaxyl M 500 + 0.5 compound Present 7 + Metalaxyl 200 + 200 compound Present 7 + Metalaxyl 500 + C.5 compound Present 7 + Metconazole 200 + 200 compound Present 7 + Metconazole 500 + 0.5 compound Present 7 + Oxathiapiprolin 200 + 200 compound Present 7 + Oxathiapiprolin 500 + 0.5 compound Present 7 + Penfurufen 200 + 200 compound Present 7 + Penfurufen 500 + 0.5 303
compound Present compound 7 + Penthiopyrad 200 + 200 compound Present compond + Penthiopyrad 500 + 0.5 compound [0365]
Table 52 (Continued)
[Table 75]
Composition Concentration (ppm) Present 7 + Picoxystrobin 200 compound + 200 Present 50. . compond 7 + Picoxystrobin 500 + 0.5 compound Present compond 7 + Prothioconazole 200 + 200 compound Present 7 + Prothioconazole 500 + 0.5 compound Present 7 + Pyraclostrobin 200 + 200 compound Present. compond 7 + Pyraclostrobin 500 + 0.5 compound Present 7 + Fungicide compound 200 + 200 compound P2 Present 7 + Fungicide compound 500 + 0.5 compound $2 Present 7 + Sedaxane 200 + 200 compound Present compond 7 + Sedaxane 500 + 0.5 compound Present 7 + Tebuconazole 200 + 200 compound Present 7 + Tebuconazole 500 + 0.5 compound Present 7 Triadimenol + 200 + 200 compound Preent7 + Triadimenol 500 + 0.5 compoundPresent20 ±20 compond 7 + Trifloxystrobin 200 + 200 compoundPresent50 +0. compond 7 + Trifloxystrobin 500 + 0.5 compoundPresent Present 7 + Triticonazole 200 + 200 compound 304
Present 7 + Triticonazole 500 + 0.5 compound [0366]
Table 53
[Table 76]
Composition Concentration (ppm) Present 8 + Clothianidin 200 + 2000 compound Present 8 + Clothianidin 500 + 50 compound Present 8 + Imidacloprid 200 + 2000 compound Present 8 + Imidacloprid 500 + 50 compound Present 8 + Thiamethoxam 200 + 2000 compound Present 8 + Thiamethoxam 500 + 50 compound Present 8 + Azoxystrobin 200 + 200 compound Present 8 + Azoxystrobin 500 + 0.5 compound Present 8 + Difenoconazole 200 + 200 compound Present 8+ Difenoconazole 500 + 0.5 compound Present 8 + Ethaboxam 200 + 200 compound Present 8 + Ethaboxam 500 + 0.5 compound Present 8 + Fludioxonil 200 + 200 compound Present 8 + Fludioxonil 500 + 0.5 compound Present 8 + Fluopyram 200 + 2000 compound Present 8 + Fluopyram 500 + 0.5 compound Present 8 + Fluoxastrobin 200 + 200 compound Present 8 + Fluoxastrobin 500 + 0.5 compound 800 + 2 Present 8 + Flutolanil 200 + 200 305
compound Present 8 + Flutolanil 500 + 0.5 compound [0367]
Table 53 (Continued)
[Table 77]
Composition Concentration (ppm) Present 8 + Flutriafol 200 + 200 compound Present 8 + Flutriafol 500 + 0.5 compound Present compond 8 + Fluxapyroxad 200 + 200 compound compound 8 + Fluxapyroxad 500 + 0.5 compound Present compond 8 + Ipconazole 200 + 200 compound Present compond 8 + Ipconazcle 500 + 0.5 compound compond 8 + Mandestrobin 200 + 200 compoundPresent Present 8 + Mandestrobin 500 + 0.5 compound Present 8 + Metalaxyl M 200 + 200 compound Present 8 + Metalaxyl M 500 + 0.5 compound Present 8 + Metalaxyl 200 + 200 compound Present 8 + Metalaxyl 500 + 0.5 compound compound 8 + Metconazole 200 + 200 compoundPresent 8 + Metconazole 500 + 0.5 compound Present compond 8 + Oxathiapiprolin 200 + 200 compound Present 8 + Oxathiapiprolin 500 + 0.5 compound Present 8 + Penfurufen 200 + 200 compound Present compond 8 + Penfurufen 500 + 0.5 compound 306
Present 8 + Penthiopyrad 200 + 200 compound Present 8 + Penthiopyrad 500 + 0.5 compound [0368]
Table 53 (Continued)
[Table 78]
composition Concentration Present 8 + Picoxystrobin 200 + 200 compound Present 8 + Picoxystrobin 500 + 0.5 compound Present 8 + Prothioconazole 200 + 200 compound Present 8 + Prothioconazole 500 + 0.5 compound Present 8 + Pyraclostrobin 200 + 200 compound Present 8 + Pyraclostrobin 500 + 0.5 compound Present 8 + Fungicide compound 200 + 200 compound P2 Present 8 + Fungicide compound 500 + 0.5 compound 8 2 Present 8 + Sedaxane 200 + 200 compound Present 8 + Sedaxane 500 + 0.5 compound Present 8 + Tebuconazole 200 + 200 compound Present 8 + Tebuconazole 500 + 0.5 compound Present 8 + Triadimenol 200 + 200 compound Present 8 + Triadimenol 500 + 0.5 compound Present 8 + Trifloxystrobin 200 + 200 compound Present 8 + Trifloxystrobin 500 + 0.5 compound Present 8 + Triticonazole 200 + 200 compound Present 8 + Triticonazole 500 + 0.5 307
compound [0369]
Table 54
[Table 791
Composition Concentration (ppm) Present 9 + Clothianidin 200 + 2000 compound Present., compond 9 + Clothianidin 500 + 50 compound Present compond 9 + Imidacloprid 200 + 2000 compound Present compond ~9 + Imidacloprid 500 + 50 compound Present 9 + Thiamethoxam 200 + 2000 compound Present compond 9 + Thiamethoxam 500 + 50 compound Present 9 + Azoxystrobin 200 + 200 compound compond 9 + Azoxystrobin 500 + 0.5 compound Present 9 + Difenoconazole 200 + 200 compound Present 9 + Difenoconazole 500 + 0.5 compound Present 9 + Ethaboxam 200 + 200 compound Present 9 + Ethaboxam 500 + 0.5 compound Present 9 + Fludioxonil 200 + 200 compound Present 9 + Fludioxonil 500 + 0.5 compound
Presed 9 + Fluopyram 200 + compoundPresent 9±Euprm20±202000 Present + Fluopyram 500 + 0.5 compound Present compond 9 + Fluoxastrobin 200 + 200 compound Present compond 9 + Fluoxastrobin 500 + 0.5 compound Present 9 + Flutolanil 200 + 200 compound 308
Present 9 + Flutolanil 500 + 0.5 compound [0370]
Table 54 (Continued)
[Table 80] Concentration composition ______(ppm) Present 9 + Flutriafol 200 + 200 compound Present 9 + Flutriafol 500 + 0.5 compound Present 9 + Fluxapyroxad 200 + 200 compound Present 9 + Fluxapyroxad 500 + 0.5 compound Present 9 + Ipconazole 200 + 200 compound Present 9 + Ipconazole 500 + 0.5 compound Present 9 + Mandestrobin 200 + 200 compound Present 9 + Mandestrobin 500 + 0.5 compound Present 9 + Metalaxyl M 200 + 200 compound Present 9 + Metalaxyl M 500 + 0.5 compound Present 9 + Metalaxyl 200 + 200 compound Present 9 + Metalaxyl 500 + 0.5 compound Present 9 + Metconazole 200 + 200 compound Present 9 + Metconazole 500 + 0.5 compound Present 9 + Oxathiapiprolin 200 + 200 compound Present 9 + Oxathiapiprolin 500 + 0.5 compound Present 9 + Penfurufen 200 + 200 compound Present 9 + Penfurufen 500 + 0.5 compound Present 9 + Penthiopyrad 200 + 200 309
compound Preent9 + Penthiopyrad 500 + 0.5 compound [0371]
Table 54 (Continued)
[Table 813
Composition Concentration ______(ppm) Present compound 9 + Picoxystrobin 200 + 200 Present compound 9 + Picoxystrobin 500 + 0.5
compoundPresent Present 9 + Prothioconazole 500 + 0.5 compound Present compound 9 + Pyraclostrobin 200 + 200 compound Present compond 9 + Pyraclostrobin 500 + 0.5 compound Present 9 + Fungicide compound 200 + 200 compound 2 Present 9 + Fungicide compound 500 + 0.5 compound 02 Present 9 + Sedaxane 200 + 200 compound Present 9 + Sedaxane 500 + 0.5 compound Present compond 9 + Tebuconazole 200 + 200 compound Present 9 + Tebuconazole 500 + 0.5 compound Present compund9 compound + Triadimenol 200 + 200 Present 9 + Triadimenol 500 + 0.5 compound Present compond 9 + Trifloxystrobin 200 + 200 compound Present compund9 compound + Trifioxystrobin 500 + 0.5 Present 9 + Triticonazole 200 + 200 compound Present500. compond 9 + Triticonazole 500 + 0.5 compoundII 310
[0372]
Table 55
[Table 82]
Composition Concentration ______(ppm) Present 10 + Clothianidin 200 + 2000 compound Present 10 + Clothianidin 500 + 50 compound Present 10 + Imidacloprid 200 + 2000 compound Present 10 + Imidacloprid 500 + 50 compound Present 10 + Thiamethoxam 200 + 2000 compound Present 10 + Thiamethoxam 500 + 50 compound Present 10 + Azoxystrobin 200 + 200 compound Present 10 + Azoxystrobin 500 + 0.5 compound Present 10 + Difenoconazole 200 + 200 compound Present 10 + Difenoconazole 500 + 0.5 compound Present 10 + Ethaboxam 200 + 200 compound Present 10 + Ethaboxam 500 + 0.5 compound Present 10 + Fludioxonil 200 + 200 compound Present 10 + Fludioxonil 500 + 0.5 compound Present 10 + Fluopyram 200 + 2000 compound Present 10 + Fluopyram 500 + 0.5 compound Present 10 + Fluoxastrobin 200 + 200 compound Present 10 + Fluoxastrobin 500 + 0.5 compound Present 10 + Flutolanil 200 + 200 compound Present 10 + Flutolanil 500 + 0.5 311
[compound [0373]
Table 55 (Continued)
[Table 83]
Composition Concentration (ppm) Present 10 + Flutriafol 200 + 200 compound Present 10 + Flutriafol 500 + 0.5 compound Present compound 10 + Fluxapyroxad 200 + 200 Present compound 10 + Fluxapyroxad 500 + 0.5 compound Present compond 10 + Ipconazole 200 + 200 compound Present compound 10 + Ipconazole 500 + 0.5 compound compond 10 + Mandestrobin 200 + 200 compound compond 10 + Mandestrobin 500 + 0.5 compound Present compond 10 + Metalaxyl M 200 + 200 compound Present 10 + Metalaxyl M 500 + 0.5 compound Present 10 + Metalaxyl 200 + 200 compound Present compond 10 + Metalaxyl 500 + 0.5 compound Present compond 10 + Metconazole 200 + 200 compound Present compound 10 + Metconazole 500 + 0.5 compound Present compound 10 + Oxathiapiprolin 200 + 200 Present compond 10 + Oxathiapiprolin 500 + 0.5 compound Present 10 + Penfurufen 200 + 200 compound Present 10 + Penfurufen 500 + 0.5 compound Present compond 10 + Penthiopyrad 200 + 200 compound 312
Present 10 + Penthiopyrad 500 + 0.5 compound [0374]
Table 55 (Continued)
[Table 841 Concentration Composition n (ppm) Present 10 + Picoxystrobin 200 + 200 compound Present 10 + Picoxystrobin 500 + 0.5 compound Present 10 + Prothioconazole 200 + 200 compound Present 10 + Prothioconazole 500 + 0.5 compound Present 10 + Pyraclostrobin 200 + 200 compound Present 10 + Pyraclostrobin 500 + 0.5 compound Present 10 + Fungicide compound s2 200 + 200 compound Present 10 + Fungicide compound P2 500 + 0.5 compound Present 10 + Sedaxane 200 + 200 compound Present 10 + Sedaxane 500 + 0.5 compound Present 10 + Tebuconazole 200 + 200 compoud Present 10 + Tebuconazole 500 + 0.5 compound Present 10 + Triadimenol 200 + 200 compound Present 10 + Triadimenol 500 + 0.5 compound Present 10 + Trifloxystrobin 200 + 200 compound Present 10 + Trifloxystrobin 500 + 0.5 compound Present 10 + Triticonazole 200 + 200 compound Present 10 + Triticonazole 500 + 0.5 compound 313
[0375]
Table 56
[Table 85]
Composition Concentration __(ppm) Present 11 + Clothianidin 200 + 2000 compound Present 11 + Clothianidin 500 + 50 compound Present 11 + Imidacloprid 200 + 2000 compound compond 11 + Imidacloprid 500 + 50 compound compond 11 + Thiamethoxam' 200 + 2000 compound compond 11 + Thiamethoxam 500 + 50 compound compond 11 + Azoxystrobin 200 + 200 compoundPresent compond 11 + Azoxystrobin 500 + 0.5 compound Present 11 + Difenoconazole 200 + 200 compound Present Present 11 + Difenoconazole 500 + 0.5 compound Present 11 + Ethaboxam 200 + 200 compound compond 11 + Ethaboxam 500 + 0.5 compound Present 11 + Fludioxonil 200 + 200 compound Present 11 + Fludioxonil 500 + 0.5 compound Present11 + Fluopyram 200 + 2000 compound Present 500 + 0.5 compound 11 + Fluopyram Present 11 + Fluoxastrobin 200 + 200 compound Present 11 + Fluoxastrobin 500 + 0.5 compound Present 11 + Flutolanil 200 + 200 compound Present 11 + Flutolanil 500 + 0.5 314
[0376]
Table 56 (Continued)
[Table 86] Concentration Composition(ppm)
Present 11 + Flutriafol 200 + 200 compound Present 11 + Flutriafol 500 + 0.5 compound Present 11 + Fluxapyroxad 200 + 200 compound Present 11 + Fluxapyroxad 500 + 0.5 compound Present 11 + Ipconazole 200 + 200 compound Present 11 + Ipconazole 500 + 0.5 compound Present 11 + Mandestrobin 200 + 200 compound Present 11 + Mandestrobin 500 + 0.5 compound Present 11 + Metalaxyl M 200 + 200 compound Present 11 + Metalaxyl M 500 + 0.5 compound Present 11 + Metalaxyl 200 + 200 compound Present 11 + Metalaxyl 500 + 0. compound Present 11 + Metconazole 200 + 200 compound Present 11 + Metconazole 500 + 0.5 compound Present 11 + Oxathiapiprolin 200 + 200 compound Present 11 + Oxathiapiprolin 500 + 0.5 compound Present 11 + Penfurufen 200 + 200 compound Present 11 + Penfurufen 500 + 0.5 compound Present 11 + Penthiopyrad 200 + 200 compound 315
Present compound 11 + Penthiopyrad 500 + 0.5
[0377]
Table 56 (Continued)
[Table 87]
Concentratio Composition n (ppm) Present. compond 11 + Picoxystrobin 200 + 200 compound compound 11 + Picoxystrobin 500 + 0.5 Present 1 + Prothioconazole 200 + 200 compound Present 11 + Prothioconazole 500 + 0.5 compound Present compond 11 + Pyraclostrobin 200 + 200 compound Present compond 11 + Pyraclostrobin 500 + 0.5 compound Present compond 11 + Fungicide compound p2 200 + 200 compound Present compond 11 + Fungicide compound p2 500 + 0.5 compound Present 11 + Sedaxane 200 + 200 compound Present 11 + Sedaxane 500 + 0.5 compound Present 11 + Tebuconazole 200 + compound 200 Present 11 + Tebuconazole 500 + 0.5 compound Present compond 11 + Triadimenol 200 + 200 compound Present 11 + Triadimenol 500 + 0.5 compound Present20 compond 11 + Trifloxystrobin 200 ++20 200 compound Present compond 11 + Trifloxystrobin 500 + 0.5 compound Present 11 + Triticonazole 200 + 200 compound Present, compond 11 + Triticonazole 500 + 0.5 compound 316
[0378)
Table 57
[Table 88] Concentration Composition(pm (ppm) Present 12 + Clothianidin 200 + 2000 compound Present 12 + Clothianidin 500 + 50 compound Present 12 + Imidacloprid 200 + 2000 compound Present 12 + Imidacloprid 500 + 50 compound Present 12 + Thiamethoxam 200 + 2000 compound Present 12 + Thiamethoxam 500 + 50 compound Present 12 + Azoxystrobin 200 + 200 compound Present 12 + Azoxystrobin 500 + 0.5 compound Present 12 + Difenoconazole 200 + 200 compound Present 12 + Difenoconazole 500 + 0.5 compound Present 12 + Ethaboxam 200 + 200 compound Present 12 + Ethaboxam 500 + 0.5 compound Present 12 + Fludioxonil 200 + 200 compound Present 12 + Fludioxonil 500 + 0.5 compound Present 12 + Fluopyram 200 + 2000 compound Present 12 + Fluopyram 500 + 0.5 compound Present 12 + Fluoxastrobin 200 + 200 compound Present 12 + Fluoxastrobin 500 + 0.5 compound Present 12 + Flutolanil 200 + 200 compound Present 12 + Flutolanil 500 + 0.5 317
compound 0379]
Table 57 (Continued)
[Table 891
Composition concentration (ppm) Present 12 -+ Flutriafol 200 + 200 compound Present 12 + Flutriafol 500 + 0.5 compound Present compond 12 + Fluxapyroxad 200 + 200 compound Present 12 + Fluxapyroxad 500 + 0.5 compound Present compond 12 + Ipconazole 200 + 200 compound Present compund12 +r Ipconazale 500 + 0.5 compound Present 12 + Mandestrobin 200 + 200 compound Present 12 + Mandestrobin 500 + 0.5 compound Present 12 + Metalaxyl M 200 + 200 compound Present 12 + Metalaxyl M 500 + 0.5 compound Present 12 + Metalaxyl 200 + 200 compound Present 12 + Metalaxyl 500 + 0.5 compound Present 12 + Metconazole 200 + 200 compound Present compond 12 + Metconazole 500 + 0.5 compound Present 12 + Oxathiapiprolin 200 + 200 compound compond 12 + Oxathiapiprolin 500 + 0.5 compound Present 12 + Penfurufen 200 200 compound Present 12 + Penfurufen 500 + 0.5 compound Present 12 + Penthiopyrad 200 + 200 compound 318
Present 12 + Penthiopyrad 500 + 0.5 compound [03801
Table 57 (Continued)
[Table 90] concentration Composition n (ppm) Present 12 + Picoxystrobin 200 + 200 compound Present 12 + Picoxystrobin 500 + 0.5 compound Present 12 + Prothioconazole 200 + 200 compound Present 12 + Prothioconazole 500 + 0.5 impound Present 12 + Pyraclostrobin 200 + 200 compound Present 12 + Pyraclostrobin 500 + 0.5 compound Present 12 + Fungicide compound P2 200 + 200 compound Present 12 + Fungicide compound P2 500 + 0.5 compound Present 12 + Sedaxane 200 + 200 compound Present 12 + Sedaxane 500 + 0.5 compound Present 12 + Tebuconazole 200 + 200 compound Present 12 + Tebuconazole 500 + 0.5 compound Present 12 + Triadimenol 200 + 200 compound Present 12 + Triadimenol 500 + 0.5 _compound Present 12 + Trifloxystrobin 200 + 200 compound Present 12 + Trifloxystrobin 500 + 0.5 compound Present 12 + Triticonazole 200 + 200 compound Present 12 + Triticonazole 500 + 0.5 compound 319
[03811
Table 58
[Table 91]
Composition Concentration (ppm) Present 13 + Clothianidin 200 + 2000 compound Present compond 13 + Clothianidin 500 + 50 compound compond 13 + Imidacloprid 200 + 2000 compound Present ~+ 5 compond 13 + Imidacloprid 500 + 50 compound Present compound 13 + Thiamethoxam 200 + 2000 Present 13 + Thiamethoxam 500 + 50 compound Present compond 13 + Azoxystrobin 200 + 200 compound Present compond 13 + Azoxystrobin 500 + 0.5 compound Present20 Present 13 + Difenoconazole 200 + 200 compound
Presentcompound 13 + Difenoconazole 500 + 0.5 Present 13 + Ethaboxam 200 + 200 compound Present 13 + Ethaboxam 500 + 0.5 compound Present 13 + Fludioxonil 200 + 200 compound Present 13 + Fludioxonil 500 + 0.5 compound Present compond 13 + Fluopyram 200 + 2000 compound Present compond 13 + Fluopyram 500 + 0.5 compound Present compond 13 + Fluoxastrobin 200 + 200 compound Present compond 13 + Fluoxastrobin 500 + 0.5 compound Present 13 + Flutolanil 200 + 200 compound Present 13 + Flutolanil 500 + 0.5 320
[0382]
Table 58 (Continued)
[Table 92]
Composition Concentration (ppm) Present 13 + Flutriafol 200 + 200 compound Present 13 + Flutriafol 500 + 0.5 compound Present 13 + Fluxapyroxad 200 + 200 compound Present 13 + Fluxapyroxad 500 + 0.5 compound Present 13 + Ipconazole 200 + 200 compound Present 13 + Ipconazole 500 + 0.5 compound Present 13 + Mandestrobin 200 + 200 compound Present 13 + Mandestrobin 500 + 0.5 compound Present 13 + Metalaxyl M 200 + 200 compound Present 13 + Metalaxyl M 500 + 0.5 compound Present 13 + Metalaxyl 200 + 200 compound Present 13 + Metalaxyl 500 + 0.5 compound Present 13 + Metconazole 200 + 200 compound Present 13 + Metconazole 500 + 0.5 compound 1 ..etcona.ole.500.+0.5 Present 13 + Oxathiapiprolin 200 + 200 compound Present 13 + Oxathiapiprolin 500 + 0.5 compound Present 13 + Penfurufen 200 + 200 compound Present 13 + Penfurufen 500 + 0.5 compound Present 13 + Penthiopyrad 200 + 200 compound 321
Preent13 + Penthiopyrad 500 + 0.5 compound [0383]
Table 58 (Continued)
[Table 93] Concentratio Composition n (ppm) Present compond 13 + Picoxystrobin 200 + 200 compound Present. compound 13 + Picoxystrobin 500 + 0.5 Present 13 + Prothioconazole 200 + 200 compound Present compond 13 + Prothioconazole 500 + 0.5 compound Present compound 13 + Pyraclostrobin 200 + 200 Present compound 13 + Pyraclostrobin 500 + 0.5
compond 13 + Fungicide compound 32 200 + 200 Present., compond 13 + Fungicide compound Q2 500 + 0.5 compound Present 13 Sedaxane + 200 + 200 compound Present compond 13 + Sedaxane 500 + 0.5 compound Present compond 13 + Tebuconazole 200 + 200 compound Present 13 + Tebuconazole 500 + 0.5 compound Present compond 13 + Triadimenol 200 + 200 compound Present compond 13 + Triadimenol 500 + 0.5 compound Present compond 13 + Trifloxystrobin 200 + 200 compound Present. compound 13 + Trifloxystrobin 500 + 0.5 Present coond 13 + Triticonazole 200 + 200 compound Present compond 13 + Triticonazole 500 + 0.5 compound 322
[03841
Table 59
[Table 94] Concentration Composition (ppm) Present 16 + Clothianidin 200 + 2000 compound Present 16 + Clothianidin 500 + 50 compound Present 16 + Imidacloprid 200 + 2000 compound Present 16 + Imidacloprid 500 + 50 compound Present 16 + Thiamethoxam 200 + 2000 compound Present 16 + Thiamethoxam 500 + 50 compound Present 16 + Azoxystrobin 200 + 200 compound Present 16 + Azoxystrobin 500 + 0.5 compound Present 16 + Difenoconazole 200 + 200 compound Present 16 + Difenoconazole 500 + 0.5 compound cPuent 16 + Ethaboxam 200 + 200 compound Present 16 + Ethaboxam 500 + 0.5 compound Present 16 + Fludioxonil 200 + 200 compound Present 16 + Fludioxonil 500 + 0.5 compound Present 16 + Fluopyram 200 + 2000 compound Present 16 + Fluopyram 500 + 0.5 compound Present 16 + Fluoxastrobin 200 + 200 compound Present 16 + Fluoxastrobin 500 + 0.5 compound Present 16 + Flutolanil 200 + 200 compound Present 16 + Flutolanil 500 + 0.5 323
compound [0385]
Table 59 (Continued)
[Table 95]
Composition Concentration (ppm) Present 16 + Flutriafol 200 + 200 compound Present 16 + Flutriafol 500 + 0.5 compound Present 16 + Fluxapyroxad 200 + 200 compound Present 16 + Fluxapyroxad 500 + 0.5 compound compond 16 + Ipconazole 200 + 200 compound Present16 + Ipconazole 500 + 0.5 compound Present 16 + Mandestrobin 200 + 200 compound Present 16 + Mandestrobin 500 + 0.5 compound Present 16 + Metalaxyl M 200 + 200 compound Present 16 + Metalaxyl M 500 + 0.5 compound Present 16 + Metalaxyl 200 + 200 compound Present 16 + Metalaxyl 500 + 0.5 compound Present 16 + Metconazole 200 + 200 compound Present 16 + Metconazole 500 + 0.5 compound compond 16 + Oxathiapiprolin 200 + 200 compound Present compond 16 + Oxathiapiprolin 500 + 0.5 compound Present 16 + Penfurufen 200 + 200 compound Present 16 + Penfurufen 500 + 0.5 compound Present compond 16 + Penthiopyrad 200 + 200 compound 324
Present 16 + Penthiopyrad 50 0 + 0. 5 compound [0386]
Table 59 (Continued)
(Table 96] Concentratio Composition n (ppm) Present 16 + Picoxystrobin 200 + 200 compound Present 16 + Picoxystrobin 500 + 0.5 compound Present 16 + Prothioconazole 200 + 200 compound Present 16 + Prothioconazole 500 + 0.5 compound Present 16 + Pyraclostrobin 200 + 200 compound Present 16 + Pyraclostrobin 500 + 0.5 compound Present 16 + Fungicide compound @2 200 + 200 compound Present 16 + Fungicide compound P2 500 + 0.5 impound Present 16 + Sedaxane 200 + 200 compound Present 16 + Sedaxane 500 + 0.5 compound Present 16 + Tebuconazole 200 + 200 compound Present 16 + Tebuconazole 500 + 0.5 compound Present 16 + Triadimenol 200 + 200 compound Present 16 + Triadimenol 500 + 0.5 compound compond 16 + Trifloxystrobin 200 + 200 cPound 16 + Trifloxystrobin 500 + 0.5 compound Present 16 + Triticonazole 200 + 200 compound Present 16 + Triticonazole 500 + 0.5 compound 325
[03871
Table 60
[Table 97]
Composition Concentration (ppm) Present 18 + Clothianidin 200 + 2000 compound Present 18 + Clothianidin 500 + 50 compound Present 18 + Imidacloprid 200 + 2000 compound Present 18 + Imidacloprid 500 + 50 compound Present 18 + Thiamethoxam 200 + 2000 compound Present 18 + Thiamethoxam 500 + 20 compound compond 18 + Azoxystrobin 200 + 200 compoundPresent50 + 0. Present 18 + Azoxystrobin 500 + 0.5 compound Present 18 + Difenoconazole 200 + 200 compound Present18 + Difenoconazoe 500 + 0.5 compoundPresent Present 8 + Ethaboxam 200 + 200 compound Present 18 + Ethaboxam 500 + 0.5 compound Present 18 + Fludioxonil 200 + 200 compound Present 18 + Fludioxonil 500 + 0.5 compound Present 18 + Fluopyram 200 + 2000 compound compond 18 + Fluopyroam 500 + 0.5 compound Present compond 18 + Fluoxastrobin 200 + 200 compound Present 18 + Fluoxastrobin 500 + 0.5 compound Present 18 + Flutolanil 200 + 200 compound Present 18 + Flutolanil 500 + 0.5 326
compound [0388]
Table 60 (Continued)
[Table 98] Concentration Composition (ppm) Present 18 + Flutriafol 200 + 200 compound Present 18 + Flutriafol 500 + 0.5 compound Present 18 + Fluxapyroxad 200 + 200 compound Present 18 + Fluxapyroxad 500 + 0.5 compound Present 18 + Ipconazole 200 + 200 compound Present 18 + Ipconazole 500 + 0.5 compound Present 18 + Mandestrobin 200 + 200 compound Present 18 + Mandestrobin 500 + 0.5 compound Present 18 + Metalaxyl M 200 + 200 compound Present 18 + Metalaxyl M 500 + 0.5 compound Present 18 + Metalaxyl 200 + 200 compound Present 18 + Metalaxyl 500 + 0.5 compound Present 18 + Metconazole 200 + 200 compound Present 18 + Metconazole 500 + 0.5 compound Present 18 + Oxathiapiprolin 200 + 200 coprsnd compond 18 + Oxathiapiprolin 500 + 0.5 compound Present 18 + Penfurufen 200 + 200 compound Present 18 + Penfurufen 500 + 0.5 compound Present 18 + Penthiopyrad 200 + 200 compound 327
Preent18 + Penthiopyrad 500 + 0.5
[0389]
Table 60 (Continued)
[Table 99]
Concentration Composition n (ppm) Present compond 18 + Picoxystrobin 200 + 200 compound
compound 18 + Picoxystrobin 500 + 0.5 Present 18 + Prothioconazole 200 + compound 200 Present50 I0. compond 18 + Prothioconazole 500 + 0.5 compound
cPound 18 + Pyraclostrobin 200 + 200 Present 18 + Pyraclostrobin 500 + 0.5 compound compond 18 + Fungicide compound @2 200 + 200 compoundPresent Present 18 + Fungicide compound 22500 + 0.5 compound
compond 18 + Sedaxane 200 + 200 compoundPresent compond 18 + Sedaxane 500 + 0.5 compoundPresent Present 18 + Tebuconazole 200 + 200 compound Present 18 + Tebuconazole 500 + 0.5 compound compond 18 + Triadimenol 200 + 200 compound compond 18 + Triadimenol 500 + 0.5 compound Present compond 18 + Trifloxystrobin 200 + 200 compound compond 18 + Trifloxystrobin 500 + 0.5 compound compond 18 + Triticonazole 200 + 200 compound Present compond 18 + Triticonazole 500 + 0.5 compound 328
[03901
Table 61
[Table 100] Concentration Composition {ppm) Present 24 + Clothianidin 200 + 2000 compound Present 24 + Clothianidin 500 + 50 compound Present 24 + Imidacloprid 200 + 2000 compound Present 24 + Imidacloprid 500 + 50 compound Present 24 + Thiamethoxam 200 + 2000 compound Present 24 + Thiamethoxam 500 + 50 compound Present 24 + Azoxystrobin 200 + 200 compound Present 24 + Azoxystrobin 500 + 0.5 compound Present 24 + Difenoconazole 200 + 200 compound Present 24 + Difenoconazole 500 + 0.5 compound Present 24 + Ethaboxam 200 + 200 compound Present 24 + Ethaboxam 500 + 0.5 compound Present 24 + Fludioxonil 200 + 200 compound Present 24 + Fludioxonil 500 + 0.5 compound Present 24 + Fluopyram 200 + 2000 compound Present 24 + Fluopyram 500 + 0.5 compound Present 24 + Fluoxastrobin 200 + 200 compound Present 24 + Fluoxastrobin 500 + 0.5 compound Present 24 + Flutolanil 200 + 200 compound Present 24 + Flutolanil 500 + 0. 5 329
[0391]
Table 61 (Continued)
[Table 101]
Composition Concentration (ppm) Present 24 + Flutriafol 200 + 200 compound Present compond 24 + Flutriafol 500 + 0.5 compound
compond 24 + Fluxapyroxad 200 + 200 compoundPresent 24 + Fluxapyroxad 500 + 00 Preent24 + Fluxapyroxad 500 + 0.5 compoundPresent compond 24 + Ipconazole 200 + 200 compoundPresent compound 24 + Ipconazole 500 + 0.5 compound Present compond 24 + Mandestrobin 200 + 200 compound Present compound 24 + Mandestrobin 500 + 0.5 compound Present 24 + Metalaxyl M 200 + 200 compound Present 24 + Metalaxyl M 500 + 0.5 compound Present 24 + Metalaxyl 200 + 200 compound Present 24 + Metalaxyl 500 + 0.5 compound Present 24 + Metconazole 200 + 200 compound Present 24 + Metconazole 500 + 0.5 compound compond 24 + Pxathiapiprolin 200 + 200 compound Present Present24 + Oxathiapiprolin 500 + 0.5 compound Present compond 24 + Penfurufen 200 + 200 compound Present 24 + Penfurufen 500 + 0. 5 compound Present compond 24 + Penthiopyrad 200 + 200 compound 330
Peet24 + Penthiopyrad 500 + 0.5 compound [0392]
Table 61 (Continued)
[Table 102] Concentratio Composition n (ppm) Present 24 + Picoxystrobin 200 + 200 compound Present 24 + Picoxystrobin 500 + 0.5 compound Present 24 + Prothioconazole 200 + 200 compound Present 24 + Prothioconazole 500 + 0.5 compound Present 24 + Pyraclostrobin 200 + 200 compound Present 24 + Pyraclostrobin 500 + 0.5 compound Present 24 + Fungicide compound 2 200 + 200 compound Present 24 + Fungicide compound @2 500 + 0.5 compound Present 24 + Sedaxane 200 + 200 compound Present 24 + Sedaxane 500 + 0.5 compound Present 24 + Tebuconazole 200 + 200 compound Present 24 + Tebuconazole 500 + 0.5 compound Present 24 + Triadimenol 200 + 200 compound Present 24 + Triadimenol 500 + 0.5 compound Present 24 + Trifloxystrobin 200 + 200 compound Present 24 + Trifloxystrobin 500 + 0.5 compound Present 24 + Triticonazole 200 + 200 compound Present 24 + Triticonazole 500 + 0.5 compound 331
Industrial Applicability
[0393]
The Present compound shows an excellent control effect
against a harmful arthropod. Also, the composition
5 comprising the Present compound and one or more kinds of
ingredients selected from the group consisting of Group (a),
Group (b), Group (c) and Group (d) shows an excellent
control effect against a harmful arthropod. 332
CLAIMS
1. A compound represented by formula (I) or its N oxide
compound:
R2
N (R 3)
N 6Ai 5 (R%
(wherein
A represents a nitrogen atom or a CR 4 ;
R4 represents a hydrogen atom, a OR, a NRR, a
cyano group, a nitro group, or a halogen atom;
10 R' represents a C2-C10 chain hydrocarbon group having
one or more halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl
group having one or more halogen atoms, a (C1-C5
alkylsulfanyl)C2-C5 alkyl group having one or more halogen
atoms, a (Cl-C5 alkylsulfinyl)C2-C5 alkyl group having one
15 or more halogen atoms, a (Cl-C5 alkylsulfonyl)C2-CS alkyl
group having one or more halogen atoms, a (C3-C7
cycloalkyl)Cl-C3 alkyl group having one or more
substituents selected from Group G, or a C3-C7 cycloalkyl
group having one or more substituents selected from Group
20 G;
R2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms, a cyclopropylmethyl group, or a 333
cyclopropyl group;
q represents 0, 1, 2, or 3;
R3 represents independently of each other, a Cl-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more
2 2 substituents selected from Group D, a OR12, a NR"lR1 , a NRilaR1 a, a NR2 9NR"R1 2 , a NR 2 90R", a NR"C (0) R' 3 , a NR 2 9NR"C (0) R' 3 , a
NR"C (0) OR 4 , a NR 2 9NR"C (0) OR 4 , a NR"lC (0) NRR1 6 , a
2 4 6 6 6 NR NR"C (0) NRRl , a N=CHNRlSRl , a N=S (0) XRRl , a S (0) yRl, a
C(0)OR 7 , a C(0)NR"R1 2 , a cyano group, a nitro group, or a halogen atom, and when q is 2 or 3, a plurality of R3 may be identical or different;
p represents 0, 1, or 2,
R6 represents independently of each other, a Cl-C6 alkyl group optionally having one or more halogen atoms, a OR", a
NR18R1 9 , a cyano group, a nitro group, or a halogen atom, and when p is 2, a plurality of R 6 may be identical or different;
R", R17, R'8 , R1 9 , R 24 and R2 9 represent independently of each other a hydrogen atom, or a Cl-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R12 represents a hydrogen atom, a Cl-C6 chain hydrocarbon group optionally having one or more halogen atoms, a Cl-C6 alkyl group having one substituent selected from Group F, or a 334
S (0) 2R2;
R 3 represents a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, or a phenyl
group optionally having one or more substituents selected
5 from Group D;
R 1 a and R12 a combine together with a nitrogen atom to
which they are attached to form a 3 to 7 membered
nonaromatic heterocyclic group optionally having one or
more substituents selected from Group E {the 3 to 7
10 membered nonaromatic heterocyclic group represents
aziridine, azetidine, pyrrolidine, imidazoline,
imidazolidine, piperidine, tetrahydropyrimidine,
hexahydropyrimidine, piperazine, azepane, oxazolidine,
isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane,
15 thiazolidine, isothiazolidine, 1,3-thiazinane,
thiomorpholine, or 1,4-thiazepane};
R1 3 represents a hydrogen atom, a C1-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a C3-C7 cycloalkyl group optionally having one or
20 more halogen atoms, a (C3-C6 cycloalkyl)Cl-C3 alkyl group
optionally having one or more halogen atoms, a phenyl group
optionally having one or more substituents selected from
Group D, or a 5 or 6 membered aromatic heterocyclic group
optionally having one or more substituents selected from
25 Group D; 335
R4 represents a Cl-C6 chain hydrocarbon group
optionally having one or more halogen atoms, a C3-C7
cycloalkyl group optionally having one or more halogen
atoms, a (C3-C6 cycloalkyl)Cl-C3 alkyl group optionally
5 having one or more halogen atoms, or a phenylCl-C3 alkyl
group {the phenyl moiety in the phenylCl-C3 alkyl group may
optionally have one or more substituents selected from
Group D};
R'5 and R 6 represent independently of each other, a
10 Cl-C6 alkyl group optionally having one or more halogen
atoms;
7 R2 and R represent independently of each other, a
hydrogen atom, or a C1-C6 alkyl group optionally having one
or more halogen atoms;
15 n and y represent independently of each other, 0, 1,
or 2;
x represents 0 or 1;
Group B: a group consisting of a Cl-C6 alkoxy group
optionally having one or more halogen atoms, a C3-C6
20 alkenyloxy group optionally having one or more halogen
atoms, a C3-C6 alkynyloxy group optionally having one or
more halogen atoms, a Cl-C6 alkylsulfanyl group optionally
having one or more halogen atoms, a Cl-C6 alkylsulfinyl
group optionally having one or more halogen atoms, a Cl-C6
25 alkylsulfonyl group optionally having one or more halogen 336
atoms, a C3-C6 cycloalkyl group optionally having one or
more halogen atoms, a cyano group, a hydroxy group, and a
halogen atom;
Group C: a group consisting of a Cl-C6 chain
5 hydrocarbon group optionally having one or more halogen
atoms, a Cl-C6 alkoxy group optionally having one or more
halogen atoms, a C3-C6 alkenyloxy group optionally having
one or more halogen atoms, a C3-C6 alkynyloxy group
optionally having one or more halogen atoms, and a halogen
10 atom;
Group D: a group consisting of a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a hydroxy group, a Cl-C6 alkoxy group optionally
having one or more halogen atoms, a C3-C6 alkenyloxy group
15 optionally having one or more halogen atoms, a C3-C6
alkynyloxy group optionally having one or more halogen
atoms, a sulfanyl group, a Cl-C6 alkylsulfanyl group
optionally having one or more halogen atoms, a Cl-C6
alkylsulfinyl group optionally having one or more halogen
20 atoms, a Cl-C6 alkylsulfonyl group optionally having one or
more halogen atoms, an amino group, a NHR, a NRR2 , a
C(O)R OC(O)R2 1 , a C(O)OR', a cyano group, a nitro group,
and a halogen atom {R2 and R t represent independently of
each other a Cl-C6 alkyl group optionally having one or
25 more halogen atoms}; 337
Group E: a group consisting of a Cl-C6 chain
hydrocarbon group optionally having one or more halogen
atoms, a Cl-C6 alkoxy group optionally having one or more
halogen atoms, a C3-C6 alkenyloxy group optionally having
5 one or more halogen atoms, a C3-C6 alkynyloxy group
optionally having one or more halogen atoms, a halogen atom,
an oxo group, a hydroxy group, a cyano group, and a nitro
group;
Group F: a group consisting of a Cl-C6 alkoxy group
10 optionally having one or more halogen atoms, an amino group,
a NHR 2 , a NR 2 1 R2 , a cyano group, a phenyl group optionally
having one or more substituents selected from Group D, a 5
or 6 membered aromatic heterocyclic group optionally having
one or more substituents selected from Group D, a C3-C7
15 cycloalkyl group optionally having one or more halogen
atoms, and a 3 to 7 membered nonaromatic heterocyclic group
optionally having one or more substituents selected from
Group C;
Group G: a group consisting of a halogen atom, and a
20 Cl-C6 haloalkyl group].
2. The compound according to claim 1 wherein R 4
represents a hydrogen atom or a halogen atom, and R3
represents a Cl-C6 chain hydrocarbon group optionally
having one or more halogen atoms, a phenyl group optionally
25 having one or more substituents selected from Group D, a 6 338
membered aromatic heterocyclic group containing one to two
nitrogen atoms {the 6 membered aromatic heterocyclic group
optionally has one or more substituents selected from Group
D}, a 5 membered aromatic heterocyclic group containing one
5 to four nitrogen atoms {the 5 membered aromatic
heterocyclic group optionally has one or more substituents
selected from Group D}, a OR1 2 , a NR11R1 2 , or a halogen atom.
3. The compound according to claim 1 wherein R3
represents a C1-C6 alkyl group having one or more halogen
10 atoms, a OR1 2, a NR11R1 2 , or a halogen atom, and R" and R12
represent independently of each other a hydrogen atom or a
C1-C3 alkyl group optionally having one or more halogen
atoms.
4. The compound according to claim 1 wherein q is 0.
15 5. The compound according to any one of claims 1 to 4
wherein p is 0 or 1, and R 6 represents a C1-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom.
6. The compound according to any one of claims 1 to 4
20 wherein p is 0.
7. The compound according to any one of claims 1 to 5
wherein R' represents a C2-C10 haloalkyl group.
8. The compound according to any one of claims 1 to 6
wherein R' represents a C2-C10 fluoroalkyl group.
25 9. The compound according to any one of claims 1 to 6
/ n n 1 /I 1 1 \ .nI I 339
wherein R represents a C2-C1O alkyl group having two or
more fluorine atoms.
10. The compound according to any one of claims 1 to 6
wherein R1 represents a C3-C5 alkyl group having four or
5 more fluorine atoms.
11. The compound according to any one of claims 1 to 10
wherein R 2 represents a Cl-C6 alkyl group optionally having
one or more halogen atoms.
12. The compound according to any one of claims 1 to 10
10 wherein R2 represents an ethyl group.
13. The compound according to claim 1 wherein
RI represents a C2-C10 haloalkyl group;
R2 represents an ethyl group;
q is 0 or 1, and R represents a Cl-C6 alkyl group
15 optionally having one or more halogen atoms, or a halogen
atom; and
p is 0 or 1, and R 6 represents a Cl-C6 alkyl group
optionally having one or more halogen atoms, or a halogen
atom.
20 14. The compound according to claim 1 wherein
RI represents a C3-CS alkyl group having four or more
fluorine atoms;
R2 represents an ethyl group;
q is 0; and
25 p is 0. 340
15. A composition comprising the compound according to any
one of claims 1 to 14, and one or more ingredients selected
from the group consisting of Groups (a), (b), (c), and (d):
Group (a): a group consisting of insecticidal ingredients,
5 miticidal ingredients, and nematicidal ingredients;
Group (b): fungicidal ingredients;
Group (c): plant growth modulating ingredients; and
Group (d): phytotoxicity-reducing ingredients.
16. A method for controlling a harmful arthropod which
10 comprises applying an effective amount of the compound
according to any one of claims 1 to 14 or the composition
according to claim 15 to a harmful arthropod or a habitat
where a harmful arthropod lives.
17. A method for controlling a harmful arthropod which
15 comprises applying an effective amount of the compound
according to any one of claims 1 to 14 or the composition
according to claim 15 to a plant or soil for growing a
plant.
18. A method for controlling a harmful arthropod which
20 comprises applying an effective amount of the compound
according to any one of claim 1 to 14 or the composition
according to claim 15 to a seed or bulb.
19. A seed or bulb carrying an effective amount of the
compound according to any one of claims 1 to 14 or the
25 composition according to claim 15. 341
20. An agent for controlling a harmful arthropod comprising the compound according to any one of claims 1 to
14 or the composition according to claim 15, and an inert carrier.
21. A compound represented by formula (M-3):
R2 (O)nS ( HO /N
(R 6) (M-3)
[wherein
A' represents a nitrogen atom or a CR4 ;
R 4 represents a hydrogen atom, a OR 2 7 , a NR 2 7 R 2 8 , a cyano group, a nitro group, or a halogen atom;
R 2 7 and R 2 8 represent independently of each other, a hydrogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms;
R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
q represents 0, 1, 2, or 3;
R3 represents independently of each other a C1-C6 chain hydrocarbon group optionally having one or more
/ n n 1 /I 1 1 \ .nI I 342
substituents selected from Group B, a phenyl group optionally having one or more substituents selected from
Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from
2 2 2 2 9 2 2 9 Group D, a OR1 , a NR11R1 , a NR11aR1 a, a NR NR11R1 , a NR 0R11, a NR"1C (O) R1 3, a NR 2 9NR"1C (O)R1 3, a NR"1C (O)OR1 4, a
NR 2 9NR11C (0)OR14, a NR1C0(O)NR1 5 R 6 , a NR 24 NR1C0(O)NR1 5 R 6 , a
N=CHNR1 5R 6 , a N=S (0)xR15 R 6, a S (0)yR 5, a C(O)OR1 7, a
C(O)NR11R1 2 , a cyano group, a nitro group, or a halogen atom, and when q is 2 or 3, a plurality of R 3 may be identical or different;
R"1, R1 7, R1 8, R1 9 , R 2 4 and R 2 9 represent independently of each other a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R1 2 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected
2 3 from Group F, or a S(O) 2 R ;
R 2 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R"a and R12a combine together with a nitrogen atom to which they are attached to form a 3 to 7 membered nonaromatic heterocyclic group optionally having one or 343
more substituents selected from Group E {the 3 to 7 membered nonaromatic heterocyclic group represents aziridine, azetidine, pyrrolidine, imidazoline, imidazolidine, piperidine, tetrahydropyrimidine, hexahydropyrimidine, piperazine, azepane, oxazolidine, isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane, thiazolidine, isothiazolidine, 1,3-thiazinane, thiomorpholine, or 1,4-thiazepane};
R1 3 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from
Group D, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from
Group D;
R1 4 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenylCl-C3 alkyl group {the phenyl moiety in the phenylCl-C3 alkyl group may optionally have one or more substituents selected from
Group D};
/ n n 1 /I 1 1 \ .nI I 344 R'5 and R 6 represent independently of each other, a C1-C6 alkyl group optionally having one or more halogen atoms;
n represents 0, 1, or 2;
x represents 0 or 1;
y represents 0, 1, or 2;
p represents 0, 1, or 2; and
R 6 represents independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms, a OR 8 , a NR18 R1 9, a cyano group, a nitro group, or a halogen atom, and when p is 2, a plurality of R 6 may be identical or different;
Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom;
Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3 C6 alkenyloxy group optionally having 345
one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom;
Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, a NHR 2 1 , a NR 2 1 R2 2 , a
C(0)R21, a OC(O)R 2 1 , a C(O)OR 2 1 , a cyano group, a nitro group, and a halogen atom {R 21 and R 2 2 represent independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms};
Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro
/ n n 1 /I 1 1 \ .nI I 346
group;
Group F: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR 2 1 , a NR 2 1 R 2 2 , a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3 to 7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from
Group C.
22. A compound represented by formula (M-4):
R2 (O)nS
N A\
(M-4)
[wherein
V represents a halogen atom;
A' represents a nitrogen atom or a CR4 ;
R 4 represents a hydrogen atom, a OR 2 7 , a NR 27 R 2 8 , a cyano group, a nitro grouop, or a halogen atom;
R 2 7 and R 2 8 represent independently of each other, a
/ n 1 /I 1 1 \ .nI I 347
hydrogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms;
R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
q represents 0, 1, 2, or 3;
R 3 represents independently of each other a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from
Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from
2 2 2 2 9 2 2 9 Group D, a OR1 , a NR11R1 , a NR11aR1 a, a NR NR11R1 , a NR 0R11, a NR"1C (O)R1 3 , a NR 2 9NR"1C (O)R1 3 , a NR"1C (O)OR1 4 , a
NR 2 9NR11C (0)OR1 4 , a NR1C0(O)NR1 5 R 6 , a NR 24 NR1C0(O)NR1 5 R 6 , a
N=CHNR1 5R 6 , a N=S (0)xR1 5 R 6 , a S (0)yR 5 , a C(O)OR1 7 , a
C(O)NR11R1 2 , a cyano group, a nitro group, or a halogen atom, and when q is 2 or 3, a plurality of R 3 may be identical or different;
R", R1 7 , R' 8 , R1 9 , R 2 4 and R2 9 represent independently of each other a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R1 2 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or a 348
23 S (0) 2R ;
R 2 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D;
R"a and R12a combine together with a nitrogen atom to which they are attached to form a 3 to 7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E {the 3 to 7 membered nonaromatic heterocyclic group represents aziridine, azetidine, pyrrolidine, imidazoline, imidazolidine, piperidine, tetrahydropyrimidine, hexahydropyrimidine, piperazine, azepane, oxazolidine, isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane, thiazolidine, isothiazolidine, 1,3-thiazinane, thiomorpholine, or 1,4-thiazepane};
R1 3 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from
Group D, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from
Group D;
/ n n 1 /I 1 1 \ .nI I 349
R1 4 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenylCl-C3 alkyl group {the phenyl moiety in the phenylCl-C3 alkyl group may optionally have one or more substituents selected from Group D};
R'5 and R 6 represent independently of each other, a C1-C6 alkyl group optionally having one or more halogen atoms;
n represents 0, 1, or 2;
x represents 0 or 1;
y represents 0, 1, or 2;
p represents 0, 1, or 2; and
R 6 represents independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms, a OR 8 , a NR18 R1 9, a cyano group, a nitro group, or a halogen atom, and when p is 2, a plurality of R 6 may be identical or different;
Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 350
alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom;
Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom;
Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, a NHR 21 , a NR 21R22 , a
C(0)R21, a OC(O)R 2 1, a C(O)OR 21 , a cyano group, a nitro group, and a halogen atom {R 21 and R2 2 represent independently of each other a C1-C6 alkyl group optionally having one or
/ n n 1 /I 1 1 \ .nI I 351
more halogen atoms};
Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;
Group F: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR 2 1 , a NR 21 R 2 2 , a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3 to 7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from
Group C.
23. A compound represented by formula (M-30):
/ n n 1 /I 1 1 \ .nI I 352
R2 (0)ns
R40
(RS (M-30)
[wherein
R4 1 represents a halogen atom or a OR';
R' represents a C2-C10 haloalkyl, or a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms ;
R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
n represents 0, 1, or 2;
p represents 0, 1, or 2; and
R6 represents independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms, a
ORk, a NRR19, a cyano group o havin one, or a halogen atom, and w he n p is 2, a plurality of R6 may be identical or different;
R1o and R19 represent independently of each other a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms.
24. A compound represented by formula (M-31):
/ n n 1 /I 1 1 \ .nI I 353
R 2 (0)ns
R40 /
NNH 2
(RS) (M-31)
[wherein
R4 1 represents a halogen atom, a C1-C4 alkoxy group, or a OR';
R' represents a C2-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group
G;
R2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
n represents 0, 1, or 2;
p represents 0, 1, or 2; and
/ n 1 /I 1 1 \ .nI I 354
R6 represents independently of each other a C1-C6 alkyl group optionally having one or more halogen atoms, a
OR 8 , a NR1 8R1 9, a cyano group, a nitro group, or a halogen atom, and when p is 2, a plurality of R 6 may be identical or different;
R1 8 and R1 9 represent independently of each other a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
Group G: a group consisting of a halogen atom, and a
Cl-C6 haloalkyl group.
Sumitomo Chemical Company, Limited Patent Attorneys for the Applicant/Nominated Person SPRUSON & FERGUSON
i/ G A/ 1 1 \ nri