United States Patent (19) 11 Patent Number: 6,057,352 Brown Et Al
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US006057352A United States Patent (19) 11 Patent Number: 6,057,352 Brown et al. (45) Date of Patent: May 2, 2000 54 FUNGICIDAL CYCLIC AMIDES WO 96/17851 6/1996 WIPO ............................... CO7F 7/08 WO 96/26.191 8/1996 WIPO ... ... CO7D 249/12 75 Inventors: Richard James Brown, Newark, Del.: WO 96/36633 11/1996 WIPO ... ... CO7D 405/04 Deborah Ann Frasier, Martinez, Calif.; WO96/36229 11/1996 WIPO ... ... A01N 43/653 Michael Henry Howard, Jr., WO 97/02255 1/1997 WIPO m CO7D 261/12 Rockland; Gerard Michael Koether, OTHER PUBLICATIONS Bear, both of Del. Zvilichovsky, G., J. Heterocyclic Chem., 24,465–470, 1987. 73 Assignee: E. I. du Pont de Nemours and Zvilichovsky, G. et al., J. Heterocyclic Chem., 25, Company, Wilmington, Del. 1307-1310, 1988. Davis, M. et al., Australian J. Chem., 30(8), 1815-1818, 21 Appl. No.: 08/952,380 1977. 22 PCT Filed: May 8, 1996 Primary Examiner Mukund J. Shah 86 PCT No.: PCT/US96/06534 Assistant Examiner Deepak R. Rao S371 Date: Nov. 13, 1997 57 ABSTRACT S 102(e) Date: Nov. 13, 1997 Compounds of Formula (I), 87 PCT Pub. No.: WO96/36616 (I) PCT Pub. Date: Nov. 21, 1996 1.Y. Nz Related U.S. Application Data x - W 63 Continuation-in-part of application No. 08/442,433, May NY 17, 1995, abandoned. A-N 60 Provisional application No. 60/004,183, Sep. 22, 1995. Ye 51) Int. Cl." ...................... C07D 249/12; CO7D 233/30; AO1N 43/74; AO1N 43/56 and their N-oxides and agriculturally Suitable Salts are 52 U.S. Cl. ....................... 514/384; 514/386; 548/263.4; disclosed which are useful as fungicides, wherein E is 548/264.6; 548/316.7: 548/325.1; 548/325.5; 1.2-phenylene optionally substituted with one of R, R", or 548/263.8 both R and R'; A is O; S; N; NR; or CR'; G is C or N; 58 Field of Search ..................................... 514/384, 359, provided that when G is C, then A is O, S or NR and the 514/386, 360; 548/263.4, 263.8, 264.6, floating double bond is attached to G, and when G is N, then 316.7, 325.1, 325.5 A is N or CR'' and the floating double bond is attached to A; W is O; S; NH; N(C-C alkyl); or NO(C-C alkyl); X 56) References Cited is OR; S(O).R'; or halogen; R is C-C alkyl; C-C, haloalkyl, C-C alkenyl, C-C haloalkenyl, C-C alky U.S. PATENT DOCUMENTS nyl, C-C haloalkynyl, C-C cycloalkyl, C-C alkylcar 4,098,896 7/1978 Edwards .................................. 424/269 bonyl; or C-C alkoxycarbonyl; R is H; C1-C alkyl; 5,108,486 4/1992 Kondo et al. ............................... 71/92 C-Chaloalkyl, C-C alkenyl: C-C haloalkenyl, C-C, 5,416,110 5/1995 Wingert et al. .. ... 514/488 alkynyl, C-C haloalkenyl, C-C cycloalkyl, C-C alky 5,474,974 12/1995 Kruger et al. ... ... 504/236 lcarbonyl: C-alkoxycarbonyl, hydroxy; C1-C alkoxy; or 5,747,516 5/1998 Brown et al. ........................... 514/359 acetyloxy; and Y, Z, R, R", R, R'' and mare as defined in FOREIGN PATENT DOCUMENTS the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling O 508 126 10/1992 European Pat. Off. ...... CO7D 231/32 plant diseases caused by fungal plant pathogens which O 617 014 9/1994 European Pat. Off. ... CO7C 327/58 44 13 669 1/1995 Germany ..................... CO7D 307/94 involves applying an effective amount of a compound of WO 94/11334 5/1994 WIPO ......... ... CO7C 70/734 Formula (I). WO95/14009 5/1995 WIPO ..... ... CO7D 249/12 WO95/18789 7/1995 WIPO .......................... CO7C 251/60 10 Claims, No Drawings 6,057,352 1 FUNGCIDAL CYCLIC AMIDES ii This application is a national filing under 35 USC 371 of International Application Number PCT/US96/06534 filed May 8, 1996 and claiming priority of U.S. Provisional S Ne Application No. 60/004,183 filed Sep. 22, 1995 which is R2 R3 --(R'), continuation-in-part of U.S. patent application Ser. No. N S 08/442,433 filed May 17, 1995, now abandoned. OR1 O BACKGROUND OF THE INVENTION wherein R" is C-C alkyl; This invention relates to certain cyclic amides, their R’ is OR or NHR; N-oxides, agriculturally Suitable Salts and compositions, and 15 R is C-Cs cycloalkyl; methods of their use as fungicides. R" is, among others, C-Clio alkoxy, C-C, alkoxycarbonyl, halogen, cyano, C-C alkylthio, The control of plant diseases caused by fungal plant C-C alkyl, or C-C haloalkyl, pathogens is extremely important in achieving high crop R and Rare C-C alkyl; and efficiency. Plant disease damage to ornamental, vegetable, n is 0–5. EP-A-656,351, WO 95/18789 and WO 95/21153 also field, cereal, and fruit crops can cause Significant reduction disclose amides and esters Similar to those in the above two in productivity and thereby result in increased costs to the publications as fungicides. consumer. Many products are commercially available for The cyclic amides of the present invention are not dis these purposes, but the need continues for new compounds 25 closed in any of the above publications. which are more effective, leSS costly, leSS toxic, environ J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988), 25, 1307, and Australian J. Chem., (1977), mentally safer or have different modes of action. 30 (8), 1815 disclose 4-nitrophenyl isoxazoles (iii), phenyl pyrazolones (iv), and aryl isothiazolinones (v) respectively. WO 94/11334 discloses certain amides and esters of Formula i as fungicides iii NO 35 r'2 cifC YR3 MeO O YCH 40 X O-N O M Me iv. 45 wherein n is 0-4, CHCHO O X is CHOCH, CHCH, or NOCH: 50 Y is O or NH; N-N R" is, among others, nitro; cyano; halogen; C1-C alkyl; M N H H C-C haloalkyl, C-C alkoxy; C-C haloalkoxy; or w C-C alkylthio; Air R is, among others, nitro, cyano, halogen, C-C alkoxy, 55 C-C alkylcarbonylanrino, or C-C alkoxycarbony MeS 21 O lamino; S-N R is, among others, R-T-C(=Z)- or R-C M (=Z)-; 60 Me Z' is, among others, O or S; However, no utility as fungicides is alleged and the cyclic Z is, among others, O or S; and amides of the present invention are not disclosed therein. T is, among others, O, S, or NR"; and 65 SUMMARY OF THE INVENTION EP-A-617,014 discloses certain amides and esters of This invention is directed to compounds of Formula I Formula ii as fungicides including all geometric and Stereoisomers, N-oxides, and 6,057,352 S 6 ring System containing one or two nonaromatic rings when Yis-CHRN(R')C(=O)N(R)-, the two R' that each include one or two Q as ring members and attached to nitrogen atoms on Said group can be taken one or two ring members independently Selected together as -(CH2)-; or from C(=O) and S(O), and any remaining rings as when Y is –CHRO-N=C(R7)NR'-, R7 and the aromatic carbocyclic rings, each multicyclic ring adjacently attached R' can be taken together as system substituted with Rand optionally substituted CH-(CH), ; -O-(CH)-, -S-(CH)-; with one or more R'; and O v) adamantyl substituted with R and optionally substi -N(C-C alkyl)-(CH)-; with the directionality tuted with one or more R'; of Said linkage defined Such that the moiety depicted each Q is independently Selected from the group on the left side of the linkage is bonded to the carbon CHR-, -NR13-, -O-, and -S(O)-; and the moiety on the right Side of the linkage is R is H; 1-2 halogen; C-C alkyl; C-C haloalkyl; bonded to the nitrogen; C-C alkoxy; C1-C haloalkoxy, C-C alkenyl, R", R7, and Rare each independently H; C1-C alkyl; C-C haloalkenyl, C-C alkynyl, C-C alkylthio; C-C cycloalkyl, or phenyl optionally Substituted with C-Chaloalkylthio; C-C alkylsulfinyl, C-C alkyl 15 halogen, C-C alkyl, C-Chaloalkyl, C-C alkoxy, Sulfonyl, C-C cycloalkyl, C-C alkenyloxy; CO C-C haloalkoxy, nitro or cyano; (C-C alkyl); NH(C-C alkyl); N(C-C alkyl); R. R. R. R. R., and R' are each independently cyano; nitro; SiR'R'R'; or GeR'R'R'; C-C alkyl, C-C alkenyl; C1-C alkoxy, or phenyl, R’ is H; 1-2 halogen; C-C alkyl, C-C haloalkyl; each R is independently C-C alkyl; C-C haloalkyl; C-C alkoxy; C1-C haloalkoxy, C-C alkenyl, C-C alkenyl, C. alkoxy, or phenyl, C-C haloalkenyl, C-C alkynyl, C-C alkylthio; R’ is H; C-C alkyl, C-C cycloalkyl; or phenyl C-Chaloalkylthio; C-C alkylsulfinyl, C-C alkyl optionally Substituted with halogen, C-C alkyl, Sulfonyl, C-C cycloalkyl, C-C alkenyloxy, CO C-C haloalkyl, C-C alkoxy, C-C haloalkoxy, (C-C alkyl); NH(C-C alkyl); N(C-C alkyl); 25 nitro or cyano; –C(R)=NOR7; cyano; nitro; SF; SiR'R'R'; or R7 and Rare each independently C-C alkoxy; C-C, GeR’RR'; or R is phenyl, benzyl, benzoyl, cycloalkyl, formylamino; C-C alkylcarbonylamino; phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, C-C alkoxycarbonylarnino; NHC(O)NH; (C-C, furanyl, pyrimidinyl, or pyrimidinyloxy each option alkyl)NHC(O)NH; (C-C alkyl)-NC(O)NH; N(C-C, ally substituted with one of R'', R', or both R'' and alkyl); piperidinyl; morpholinyl, cyano; or nitro, R12; R’ is C-C alkoxy; C-C cycloalkyl; formylamino; each R" is independently halogen; C1-C, alkyl, C-C, C-C alkylcarbonylamino; C-C alkoxycarbony haloalkyl, C-C alkoxy, nitro, or cyano, or lamino; NHC(O)NH; (C-C, alkyl)NHC(O)NH; when R and an R' are attached to adjacent atoms on Z.