Fungicidal compositions

Abstract

A composition suitable for control of diseases caused by phytopathogens comprising (A) a compound of formula Iwherein R1 is difluoromethyl or trifluoromethyl and X is chloro, fluoro or bromo; and (B) at least one compound selected from compounds known for their fungicidal activity; and a method of controlling diseases on useful plants, especially rust diseases on soybean plants.

What is claimed is: 
     
         1 . A composition, comprising:
 (A) a compound of formula (I)   
       
         
           
           
               
               
           
         
       
       wherein R 1  is difluoromethyl and X is chloro; and
 (B) mancozeb. 
 
     
     
         2 . The composition of  claim 1 , further comprising:
 (C) at least one of:   
       azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, a compound of formula B-1.1 
       
         
           
           
               
               
           
         
       
       azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, diclobutrazol, etaconazole, furconazole, furconazole-cis and quinconazole, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine, piperalin, a compound of formula B-3.1 
       
         
           
           
               
               
           
         
       
       cyprodinil, mepanipyrim, pyrimethanil, anilazine, arsenates, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, biphenyl, bitertanol, blasticidin-S, bordeaux mixture, boscalid, bupirimate, cadmium chloride, captafol, captan, carbendazim, carbon disulfide, carboxin, carpropamid, cedar leaf oil, chinomethionat, chlorine, chloroneb, chlorothalonil, chlozolinate, cinnamaldehyde, copper, copper ammoniumcarbonate, copper hydroxide, copper octanoate, copper oleate, copper sulphate, cyazofamid, cycloheximide, cymoxanil, dichlofluanid, dichlone, dichloropropene, diclocymet, diclomezine, dicloran, diethofencarb, diflumetorim, dimethirimol, dimethomorph, dinocap, dithianon, dodine, edifenphos, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamiphos, fenarimol, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flusulfamide, flutolanil, folpet, formaldehyde, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, flyodin, fuazatine, hexachlorobenzene, hymexazole, iminoctadine, iodocarb, iprobenfos, iprodione, iprovalicarb, isoprothiolane, kasugamycin, maneb, manganous dimethyldithiocarbamate, mefenoxam, mepronil, mercuric chloride, mercury, metalaxyl, methasulfocarb, metiram, metrafenone, nabam, neem oil (hydrophobic extract), nuarimol, octhilinone, ofurace, oxadixyl, oxine copper, oxolinic acid, oxycarboxin, oxytetracycline, paclobutrazole, paraffin oil, paraformaldehyde, pencycuron, pentachloronitrobenzene, pentachlorophenol, penthiopyrad, perfurazoate, phosphoric acid, polyoxin, polyoxin D zinc salt, potassium bicarbonate, probenazole, procymidone, propamocarb, propineb, proquinazid, prothiocarb, pyrazophos, pyrifenox, pyroquilon, quinoxyfen, quintozene, silthiofam, sodium bicarbonate, sodium diacetate, sodium propionate, streptomycin, sulphur, TCMTB, tecloftalam, tecnazene, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanide, triazoxide,  Trichoderma harzianum , tricyclazole, triforine, triphenyltin hydroxide, validamycin, vinclozolin, zineb, ziram, zoxamide, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenyl sulfone, 
       a compound of formula B-5.1 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.2 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.3 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.4 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.5 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.6 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.7 
       
         
           
           
               
               
           
         
       
       3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl-phenyl)-amide (compound B-5.8), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (compound B-5.9), 1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid [2-(1,3-dimethylbutyl)phenyl]-amide (compound B-5.10), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-amide (compound B-5.11), N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (compound B-5.12), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-amide (compound B-5.13), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-amide (compound B-5.14), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-amide (compound B-5.15), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(4′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.16), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(2′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.17) and 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(2′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.18), acibenzolar-S-methyl, chlormequat chloride, ethephon, mepiquat chloride, trinexapc-ethyl, abamectin, clothianidin, emamectin benzoate, imidacloprid, tefluthrin, thiamethoxam, glyphosate, a compound of formula V 
       
         
           
           
               
               
           
         
       
       fomesafen, a racemic compound of formula VIa (syn) 
       
         
           
           
               
               
           
         
       
       wherein Ra 7  is trifluoromethyl or difluoromethyl; 
       a racemic mixture of formula VIb (anti) 
       
         
           
           
               
               
           
         
       
       wherein Ra 7  is trifluoromethyl or difluoromethyl, and a compound of formula VIc 
       
         
           
           
               
               
           
         
       
       which is an epimeric mixture of racemic compounds of formulae F-10 (syn) and F-11 (anti), wherein the ratio from racemic compounds of formula F-10 (syn) to racemic compounds of formula F-11 (anti) is from 1000:1 to 1:1000 and wherein Ra 7  is trifluoromethyl or difluoromethyl. 
     
     
         3 . The composition of  claim 1 , further comprising:
 (C) at least one of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, a compound of formula B-1.1   
       
         
           
           
               
               
           
         
       
       azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, penconazole, prochloraz, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, etaconazole, bitertanol, famoxadone, fenamidone, fenarimol, nuarimol, pyrifenox, and triforine. 
     
     
         4 . The composition of  claim 2 , wherein there is only one of (C). 
     
     
         5 . The composition of  claim 2 , wherein the agrochemical combination of the composition consists of (A), (B), and (C). 
     
     
         6 . The composition of  claim 5 , wherein there is only one of (C). 
     
     
         7 . The composition of  claim 3 , wherein there is only one of (C). 
     
     
         8 . The composition of  claim 3 , wherein the agrochemical combination of the composition consists of (A), (B), and (C). 
     
     
         9 . The composition of  claim 8 , wherein there is only one of (C). 
     
     
         10 . A composition, comprising:
 (A) a compound of formula (I)   
       
         
           
           
               
               
           
         
       
       wherein R 1  is difluoromethyl and X is chloro; and
 (B) prothioconazole; and 
 (C) at least one of: 
 
       azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, a compound of formula B-1.1 
       
         
           
           
               
               
           
         
       
       azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, pefurazoate, penconazole, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, diclobutrazol, etaconazole, furconazole, furconazole-cis and quinconazole, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine, piperalin, a compound of formula B-3.1 
       
         
           
           
               
               
           
         
       
       cyprodinil, mepanipyrim, pyrimethanil, anilazine, arsenates, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, biphenyl, bitertanol, blasticidin-S, bordeaux mixture, boscalid, bupirimate, cadmium chloride, captafol, captan, carbendazim, carbon disulfide, carboxin, carpropamid, cedar leaf oil, chinomethionat, chlorine, chloroneb, chlorothalonil, chlozolinate, cinnamaldehyde, copper, copper ammoniumcarbonate, copper hydroxide, copper octanoate, copper oleate, copper sulphate, cyazofamid, cycloheximide, cymoxanil, dichlofluanid, dichlone, dichloropropene, diclocymet, diclomezine, dicloran, diethofencarb, diflumetorim, dimethirimol, dimethomorph, dinocap, dithianon, dodine, edifenphos, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenaminosulf, fenamiphos, fenarimol, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flusulfamide, flutolanil, folpet, formaldehyde, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, flyodin, fuazatine, hexachlorobenzene, hymexazole, iminoctadine, iodocarb, iprobenfos, iprodione, iprovalicarb, isoprothiolane, kasugamycin, mancozeb, maneb, manganous dimethyldithiocarbamate, mefenoxam, mepronil, mercuric chloride, mercury, metalaxyl, methasulfocarb, metiram, metrafenone, nabam, neem oil (hydrophobic extract), nuarimol, octhilinone, ofurace, oxadixyl, oxine copper, oxolinic acid, oxycarboxin, oxytetracycline, paclobutrazole, paraffin oil, paraformaldehyde, pencycuron, pentachloronitrobenzene, pentachlorophenol, penthiopyrad, perfurazoate, phosphoric acid, polyoxin, polyoxin D zinc salt, potassium bicarbonate, probenazole, procymidone, propamocarb, propineb, proquinazid, prothiocarb, pyrazophos, pyrifenox, pyroquilon, quinoxyfen, quintozene, silthiofam, sodium bicarbonate, sodium diacetate, sodium propionate, streptomycin, sulphur, TCMTB, tecloftalam, tecnazene, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanide, triazoxide,  Trichoderma harzianum , tricyclazole, triforine, triphenyltin hydroxide, validamycin, vinclozolin, zineb, ziram, zoxamide, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenyl sulfone, 
       a compound of formula B-5.1 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.2 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.3 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.4 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.5 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.6 
       
         
           
           
               
               
           
         
       
       a compound of formula B-5.7 
       
         
           
           
               
               
           
         
       
       3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl-phenyl)-amide (compound B-5.8), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (compound B-5.9), 1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid [2-(1,3-dimethylbutyl)phenyl]-amide (compound B-5.10), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-amide (compound B-5.11), N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (compound B-5.12), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-amide (compound B-5.13), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-amide (compound B-5.14), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-amide (compound B-5.15), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(4′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.16), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(2′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.17) and 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-(2′-trifluoromethyl-biphen-2-yl)-amide (compound B-5.18), acibenzolar-S-methyl, chlormequat chloride, ethephon, mepiquat chloride, trinexapc-ethyl, abamectin, clothianidin, emamectin benzoate, imidacloprid, tefluthrin, thiamethoxam, glyphosate, a compound of formula V 
       
         
           
           
               
               
           
         
       
       fomesafen, a racemic compound of formula VIa (syn) 
       
         
           
           
               
               
           
         
       
       wherein Ra 7  is trifluoromethyl or difluoromethyl; 
       a racemic mixture of formula VIb (anti) 
       
         
           
           
               
               
           
         
       
       wherein Ra 7  is trifluoromethyl or difluoromethyl, and a compound of formula VIc 
       
         
           
           
               
               
           
         
       
       which is an epimeric mixture of racemic compounds of formulae F-10 (syn) and F-11 (anti), wherein the ratio from racemic compounds of formula F-10 (syn) to racemic compounds of formula F-11 (anti) is from 1000:1 to 1:1000 and wherein Ra 7  is trifluoromethyl or difluoromethyl. 
     
     
         11 . The composition of  claim 10 , wherein (C) is at least one of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, a compound of formula B-1.1 
       
         
           
           
               
               
           
         
       
       azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, mancozeb, metconazole, myclobutanil, oxpoconazole, penconazole, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, etaconazole, bitertanol, famoxadone, fenamidone, fenarimol, nuarimol, pyrifenox, and triforine. 
     
     
         12 . The composition of  claim 10 , wherein there is only one of (C). 
     
     
         13 . The composition of  claim 10 , wherein the agrochemical combination of the composition consists of (A), (B), and (C). 
     
     
         14 . The composition of  claim 13 , wherein there is only one of (C). 
     
     
         15 . The composition of  claim 11 , wherein there is only one of (C). 
     
     
         16 . The composition of  claim 11 , wherein the agrochemical combination of the composition consists of (A), (B), and (C). 
     
     
         17 . The composition of  claim 16 , wherein there is only one of (C). 
     
     
         18 . A composition suitable for control of diseases caused by phytopathogens, comprising:
 a synergistically effective amount of:
 (A) a compound of formula I 
   
       
         
           
           
               
               
           
         
         wherein R 1  is difluoromethyl or trifluoromethyl and X is chloro, fluoro or bromo, and
 (B2) an azole fungicide; and 
 
       
       wherein the composition further comprises mancozeb. 
     
     
         19 . The composition of  claim 18 , wherein component (A) is a compound of formula (I), wherein R 1  is difluoromethyl and X is chloro. 
     
     
         20 . The composition of  claim 19 , wherein component (B2) is prothioconazole. 
     
     
         21 . The composition of  claim 20 , wherein the weight ratio of (A) to (B2) is from 2000:1 to 1:1000. 
     
     
         22 . A method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof a composition according to  claim 20 . 
     
     
         23 . A method of controlling diseases on soybean plants caused by phytopathogens, which comprises applying to the soybean plants or to the locus thereof a composition according to  claim 20 . 
     
     
         24 . The method according to  claim 23 , wherein the phytopathogen is  Phakopsora pachyrhizi.