Substituted benzene fungicides

1. A compound selected from Formula 1, N-oxides and salts thereof,

wherein

each R 1 and R 2 is independently H, halogen, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 15 trialkylsilyl or C 3 -C 15 halotrialkylsilyl;

V is NR 3 ;

R 3 is H, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl;

R 4 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino or C 3 -C 6 cycloalkylamino;

W is O or S;

Q is CR 6a R 6b , or NR 7 ;

Y is Z;

Z is;

R 6a is H, OH, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylsulfonyl;

R 6b is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; or

R 6a and R 6b are taken together with the carbon atom to which they are attached to form a C 3 -C 6 cycloalkyl ring or C 3 -C 6 halocycloalkyl ring;

R 7 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;

each R 14 is independently H, halogen, cyano, hydroxy, amino, nitro, —CH(═O) or —C(═O)NH 2 ; or C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 2 -C 8 alkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 1 -C 6 alkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl, naphthalenyl or G A , each optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, —CH(═O),—C(═O)OH,—C(═O)NH 2 , —C(R 15 )═N—O—R 16 , —C(R 15 )═N—R 16 , C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 1 -C 6 alkylthio, benzylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 C 6 haloalkylsulfonylamino and G B ;

each G A is independently a phenyl ring, benzyl, benzyloxy, benzoyl, phenoxy or phenylsulfonyl or a 5-or 6-membered heteroaromatic ring;

each G B is independently a phenyl ring or a 5-or 6-membered heteroaromatic ring each optionally substituted with one or more substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy and C 1 -C 6 alkylthio;

each R 15 is H, C 1 -C 3 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 3 haloalkyl;

each R 16 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl; and

m is 1 or 2.

2. A compound of claim 1 wherein:

R 1 is halogen, CN, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkyl or C 1 -C 2 haloalkoxy;

R 2 is H, halogen, CN, methyl or trifluoromethyl;

R 3 is H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;

R 4 is C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylamino or C 2 C 4 dialkylamino; and

W is O.

3. A compound of claim 2 wherein:

R 1 is halogen, CN, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;

R 2 is H or halogen;

R 3 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; and

R 4 is C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy.

4. A compound of claim 3 wherein:

each R 14 is independently C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy or G A , each optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, —CH(═O), —C(═O)OH, —C(═O)NH 2 , C(R 15 )═N—O—R 16 , C(R 15 )═N—R 16 , C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy and C 3 -C 10 trialkylsilyl.

5. A compound of claim 4 wherein:

each G A is independently phenyl or 1,2,4-thiadiazole, each optionally substituted with one or more substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy and C 3 -C 10 trialkylsilyl.

6. A compound of claim 3 wherein Q is CR 6a R 6b .

7. A compound of claim 3 wherein

each R 14 is independently C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or G A , each optionally substituted with one or more substituents independently selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, —CH(═O), —C(═O)OH, —C(═O)NH 2 , C(R 15 )═N—O—R 16 , C(R 15 )═N—R 16 , C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy and C 3 -C 10 trialkylsilyl.

8. A compound of claim 1 which is selected from the group consisting of:

methyl N-[[2-chloro-5-[1-(4-chlorophenyl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate;

methyl N-[[2-chloro-5-[1-(4-methoxyphenyl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate;

methyl N-[[5-[1-(4-acetylphenyl)-1H-pyrazol-3-yl]-2-chlorophenyl]methyl]carbamate;

methyl N-[[2-chloro-5-[1-[3-(trimethylsilyl)propyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate; and

methyl N-[[2-chloro-5-[1-[4-(methylphenyl)methyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate.

9. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one compound that is fungicidal.

10. A fungicidal composition comprising (1) a fungicidally effective amount of a compound of claims 1 ; and (2) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

11. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of claim 1 .

12. The fungicidal composition of claim 9 wherein component (b) comprises at least one compound selected from the group consisting of: acibenzolar-S-methyl, aldimorph, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, bethoxazin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture, boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carboxin, carpropamid, chloroneb, chlorothalonil, chlozolinate, clotrimazole, copper oxychloride, copper salts such as copper sulfate and copper hydroxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole M, dinocap, dithianon, dodemorph, dodine, edifenphos, enestroburin, epoxiconazole, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methasulfocarb, metiram, metominostrobin, metrafenone, myclobutanil, naftifine, neo-asozin, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefurazoate, penconazole, pencycuron, penthiopyrad, phosphorous acid and salts thereof, phthalide, picobenzamid, picoxystrobin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propamocarb-hydrochloride, propiconazole, propineb, proquinazid, prothiocarb, prothioconazole, pryazophos, pyraclostrobin, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyrrolnitrin, pyroquilon, quinomethionate, quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, validamycin, valiphenal, vinclozolin, zineb, ziram, zoxamide, N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide, N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, α-[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)-phenyl]-ethoxy]imino]methyl]benzeneacetamide, 2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide, 2-[[2-fluoro-5-(trifluoromethyl)phenyl]thio]-2-[3-(2-methoxyphenyl)-2-thiazolidinylidene]acetonitrile, 2-butoxy-6-iodo-3-propyl-4H-1-benzopyran-4-one, 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine, 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]-methyl]propyl]carbamate, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide, N-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3 difluorophenyl]methylene]benzeneacetamide, N′-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyll-N-ethyl-N-methylmethanimidamide, and 1-[(2-propenylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino-1H-pyazol-3-one.

13. The fungicidal composition of claim 9 wherein component (b) comprises at least one compound selected from the group consisting of: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, clotrimazole, imazalil, oxpoconazole, prochloraz, pefurazoate, triflumizole, fenarimol, nuarimol, triforine and pyrifenox.

14. The fungicidal composition of claim 9 wherein component (b) comprises at least one compound selected from the group consisting of: benodanil, flutolanil, mepronil, fenfuram, carboxin, oxycarboxin, thifluzamide, furametpyr, penthiopyrad, bixafen, N-[2-(1S,2R)-[1,1′-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide and boscalid.

15. The fungicidal composition of claim 9 wherein component (b) comprises at least one compound selected from the group consisting of: azoxystrobin, enestroburin, picoxystrobin, pyraclostrobin, kresoxim-methyl, trifloxystrobin, dimoxystrobin, metominostrobin, orysastrobin, α[methoxyimino]-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]-ethoxy]imino]methyl]benzeneacetamide, 2-[[[3-(2,6-dichlorophenyl)-1-methyl-2-propen-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide, famoxadone, fluoxastrobin, fenamidone and pyribencarb.

16. The fungicidal composition of claim 9 wherein component (b) comprises at least one compound selected from the group consisting of: copper oxychloride, copper sulfate, copper hydroxide, Bordeaux mixture (tribasic copper sulfate), elemental sulfur, mancozeb, metiram, propineb, ferbam, maneb, thiram, zineb, ziram, folpet, captan, captafol, chlorothalonil, dichlofluanid, tolyfluanid, dodine, guazatine, iminoctadine albesilate, iminoctadine triacetate, anilazine and dithianon.