Fungicidal composition and method for controlling plant diseases

Abstract

A fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative represented by the following formula or its salt: wherein X is a halogen atom, a nitro group, a substitutable hydrocarbon group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group, a hydroxyl group, a substitutable alkylthio group, a cyano group, a carboxyl group which may be esterified or amidated, or a substitutable amino group, n is 1, 2, 3 or 4; R 1 is a substitutable alkyl group, R 2′ is a substitutable alkyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group or a hydroxyl group, p is 1, 2 or 3, and R 2″ is a substitutable alkoxy group or a hydroxyl group, provided that at least two of R 2′ and R 2″ optionally form a condensed ring containing an oxygen atom and (b) at least one other fungicide.

1 . A fungicidal composition containing as active ingredients (a) a benzoylpyridine derivative represented by the formula (I) or its salt:  
     
       
         
         
             
             
         
       
     
     (wherein X is a halogen atom, a nitro group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group, a hydroxyl group, a substitutable hydrocarbon group, a substitutable alkylthio group, a cyano group, a carboxyl group which may be esterified or amidated, or a substitutable amino group, n is 1, 2, 3 or 4; R 1  is a substitutable alkyl group, R 2′  is a substitutable alkyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group or a hydroxyl group, p is 1, 2 or 3, and R 2′  is a substitutable alkoxy group or a hydroxyl group, provided that at least two of R 2′  and R 2″  may form a condensed ring containing an oxygen atom) and (b) at least one fungicide selected from the group consisting of a strobilurin compound, an azole compound, a morpholine compound, a pyrimidinamine compound, a guanidine compound, an organic chlorine compound, an imidazole compound, an antibiotic, a pyridinamine compound, a quinoxaline compound, a dithiocarbamate compound, a cyanoacetamide compound, a phenylamide compound, a sulfenic acid compound, a copper compound, an isoxazole compound, an organophosphorus compound, a N-halogenothioalkyl compound, a dicarboxyimide compound, a benzanilide compound, piperazine compound, a pyridine compound, a carbinol compound, a piperidine compound, an organotin compound, an urea compound, a cynnamic acid compound, a phenyl carbamate compound, a cyanopyrrole compound, an oxazolidinone compound, a thiazole carboxyamide compound, a silyl amide compound, an aminoacid amidecarbamate compound, an imidazolidine compound, a hydroxyanilide compound, an oxime ether compound, a phenoxyamide compound, a benzophenone compound, Isoprothiolane, Pyroquilon, Dichlomezine, Quinoxyfen, Propamocarb Hydrochloride, Chloropicrin, Dazomet, Metam-sodium, Nicobifen, Diclocymet and Proquinazid.  
   
   
       2 . The fungicidal composition according to  claim 1 , wherein the fungicide (b) is at least one member selected from the group consisting of Kresoxim-Methyl, Azoxystrobin, Metominofen, Trifloxystrobin, Picoxystrobin, Oryzastrobin, Dimoxystrobin, Fluoxastrobin, Epoxiconazole, Triflumizole, Oxpoconazole fumarate, Tebuconazole, Imibenconazole, Tetraconazole, Triadimefon, Bitertanol, Etaconazole, Propiconazole, Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Hexaconazole, Furconazole cis, Prochloraz, Metconazole, Sipconazole, Prothioconazole, Simeconazole, Tricyclazole, Probenazole, Fluquinconazole, Triadimenol, Fenpropimorph, Spiroxamine, Mepanipyrim, Pyrimethanil, Cyprodinil, Iminoctadine, Chlorothalonil, Fthalide, Quintozene, Cyazofamid, Benomyl, Thiophanate-Methyl, Carbendazim, Polyoxins, Fluazinam, Quinomethionate, Maneb, Zineb, Mancozeb, Polycarbamate, Metiram, Propineb, Cymoxanil, Metalaxyl, Metalaxyl M, oxadixyl, Ofurace, Benalaxyl, Furalaxyl, Cyprofuram, Dichlofluanid, Cupric hydroxide, Oxine Copper, Hymexazol, Fosetyl-Al, Tolcofos-Methyl, S-benzyl O,O-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate, aluminum ethyl hydrogen phosphonate, Captan, Captafol, Folpet, Procymidone, Iprodione, Vinclozolin, Flutolanil, Mepronil, Zoxamid, Tiadinil, Triforine, Pyrifenox, Fenarimol, Flutriafol, Fenpropidine, Fentin Hydroxide, Fentin Acetate, Pencycuron, Dimethomorph, Flumorph, Diethofencarb, Fludioxonil, Fenpiclonil, Famoxadone, Ethaboxam, Silthiopham, Iprovalicarb, Benthiavalicarb, Fenamidone, Fenhexamid, Flusulfamid, Cyflufenamid, Fenoxanil, Isoprothiolane, Pyroquilon, Diclomezine, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin, Dazomet, Metam-sodium, Nicobifen, Metrafenone, Diclocymet and Proquinazid.  
   
   
       3 . The fungicidal composition according to  claim 1 , wherein fungicide (b) is at least one member selected from the group consisting of a strobilurin compound, an azole compound, a morpholine compound, a pyrimidinamine compound, a guanidine compound, an organic chlorine compound, an imidazole compound, an antibiotic, a piperidine compound and a benzophenone compound.  
   
   
       4 . The fungicidal composition according to  claim 3 , wherein the fungicide (b) is at least one member selected from the group consisting of Kresoxim-Methyl, Azoxystrobin, Epoxiconazole, Triflumizole, Oxpoconazole fumarate, Tebuconazole, Imibenconazole, Tetraconazole, Cyproconazole, Metconazole, Fluquinconazole, Triadimenol, Fenpropimorph, Spiroxamine, Mepanipyrim, Iminoctadine, Chlorothalonil, Cyazofamid, Polyoxins, Fenpropidine and Metrafenone.  
   
   
       5 . The fungicidal composition according to  claim 1 , wherein the benzoylpyridine derivative is a compound represented by the formula (I′):  
     
       
         
         
             
             
         
       
     
     (wherein when A is —N═, B is —CX 4 ═; when A is —CH═, B is —CN═; each of X 1  and X 2  which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3  group or an alkylthio group; X 3  is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3  group or an alkylthio group; X 4  is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3  group or an alkylthio group; R 1  is an alkyl group; R 2′  is an alkoxy group; p is 1, 2 or 3; and each of R 2″  and R 2′″  is an alkoxy group).  
   
   
       6 . The fungicidal composition according to  claim 5 , wherein the benzoylpyridine derivative is a compound represented by the formula (I′-1):  
     
       
         
         
             
             
         
       
     
     (wherein each of X 1  and X 2  which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3  group or an alkylthio group; X 3  is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3  group or an alkylthio group; R 1  is an alkyl group; R 2′  is an alkoxy group; p is 1, 2 or 3; and each of R 2″  and R 2′″  is an alkoxy group).  
   
   
       7 . The fungicidal composition according to  claim 6 , wherein the benzoylpyridine derivative is at least one member selected from the group consisting of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-5-chloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-ethyl-2-methoxypyridine, 3-(4,5-dimethoxy-2-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(5-ethoxy-4-methoxy-2-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-5-chloro-2-ethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-ethoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-ethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-5-iodo-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-iodo-2,4-dimethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylthiopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2,4-dimethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dibromo-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-2-methoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-iodopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-methoxy-4,5-dimethylpyridine, 3-(2-ethoxy-3,4-dimethoxy-6-methylbenzoyl)-2-ethoxy-4,5-dimethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dimethyl-2-methylthiopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-2-methoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-5-trifluoromethyl-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-trifluoromethyl-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-trifluoromethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-5-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-ethinyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-fluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-fluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-fluoromethyl-2-methoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-difluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-ethyl-4-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine and 3-(4,5-dimethoxy-2-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine.  
   
   
       8 . The fungicidal composition according to  claim 5 , wherein the benzoylpyridine derivative is a compound represented by the formula (I′-2):  
     
       
         
         
             
             
         
       
     
     (wherein each of X 1  and X 2  which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3  group or an alkylthio group; X 3  is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3  group or an alkylthio group; X 4  is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3  group or an alkylthio group; R 1  is an alkyl group; R 2′  is an alkoxy group; p is 1, 2 or 3; and each of R 2″  and R 2′″  is an alkoxy group).  
   
   
       9 . The fungicidal composition according to  claim 8 , wherein the benzoylpyridine derivative is at least one compound selected from the group consisting of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3-trifluoromethylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,3,5-trichloropyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3,5-dichloropyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3-chloro-5-methoxypyridine and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-bromo-5-methylpyridine).  
   
   
       10 . The fungicidal composition according to  claim 1 , wherein the mixing weight ratio of the benzoylpyridine derivative or its salt (a) to the fungicide (b) is from 1:10,000 to 10,000:1.  
   
   
       11 . A method for controlling plant diseases, which comprises applying the fungicidal composition as defined in  claim 1  to plants.