Synergistic Fungicidal Active Compounde Combinations Containing a Carboxamide, an Azole, a Second Azole or a Strobilurin

Abstract

The present invention relates to novel active compound combinations comprising a known carboxamide, a known azole and additionally a second known azole or alternatively a known strobilurin, which combinations are highly suitable for controlling unwanted phytopathogenic fungi.

1 . Fungicidal active compound combinations, comprising
 (A) a carboxamide of the general formula (I)   
     
       
         
         
             
             
         
       
       
         A represents one of the radicals A1 to A8 below: 
       
     
     
       
         
         
             
             
         
       
       
         R 1  represents methyl, ethyl, n- or isopropyl, 
         R 2  represents iodine, methyl, difluoromethyl or trifluoromethyl, 
         R 3  represents hydrogen, fluorine, chlorine or methyl, 
         R 4  represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl, 
         R 5  represents hydrogen, chlorine, methyl, amino or dimethylamino, 
         R 6  represents methyl, difluoromethyl or trifluoromethyl, 
         R 7  represents bromine or methyl, 
         R 8  represents methyl or trifluoromethyl, 
         R 9  represents chlorine or trifluoromethyl, 
         Y represents one of the radicals Y1 to Y4 below: 
       
     
     
       
         
         
             
             
         
       
       
         R 10  represents hydrogen or fluorine, 
         X represents —CH 2 — or O (oxygen), 
         Z represents one of the radicals Z1 or Z2 below: 
       
     
     
       
         
         
             
             
         
       
       
         R 11  represents hydrogen, fluorine, chlorine, methyl, ethyl, n-, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl or trichloromethyl, 
         R 12  represents fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethoxy, —CH═N—OCH 3  or —C(CH 3 )═N—OCH 3 , 
         R 13  represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl; 
       
       and 
       (B) an azole of the general formula (II) 
     
     
       
         
         
             
             
         
       
       
         Q represents hydrogen or SH, 
         m represents 0 or 1, 
         R 14  represents hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy, 
         R 15  represents hydrogen or chlorine, 
         A 1  represents a direct bond, —CH 2 —, —(CH 2 ) 2 — or —O—, 
         A 1  furthermore represents *—CH 2 —CHR 18 — or *—CH═CR 18 —, where the bond marked by the * is attached to the phenyl ring, and 
         R 16  and R 18  together represent —CH 2 —CH 2 —CH[CH(CH 3 ) 2 ]— or —CH 2 —CH 2 —C(CH 3 ) 2 —, 
         A 2  represents C or Si (silicon), 
         A 1  furthermore represents —N(R 18 )— and A 2  furthermore together with R 16  and R 17  represents the group C═N—R 6 , in which case R 18  and R 19  together represent the group 
       
     
     
       
         
         
             
             
         
       
       
          where the bond marked by * is attached to R 18 , 
         R 16  represents hydrogen, hydroxyl or cyano, 
         R 17  represents 1-cyclopropylethyl, 1-chlorocyclopropyl, C 1 -C 4 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 2 -haloalkoxy-C 1 -C 2 -alkyl, trimethylsilyl-C 1 -C 2 -alkyl, monofluorophenyl or phenyl, 
         R 16  and R 17  furthermore together represent —O—CH 2 —CH(R 19 )—O—, —O—CH 2 —CH(R 19 )—CH 2 — or —O—CH-(2-chlorophenyl)-, 
         R 19  represents hydrogen, C 1 -C 4 -alkyl or bromine; 
       
       and 
       (C1) a second azole of the formula (II) (as described above) 
       or 
       (C2) a strobilurin of the formula (III) 
     
     
       
         
         
             
             
         
       
       
         A 3  represents one of the groups 
       
     
     
       
         
         
             
             
         
       
       
         A 4  represents NH or O, 
         A 5  represents N or CH, 
         L represents one of the groups 
       
     
     
       
         
         
             
             
         
       
       
         
           where the bond marked by an asterisk (*) is attached to the phenyl ring, 
         
         R 20  represents phenyl, phenoxy or pyridinyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, cyano, methyl and trifluoromethyl, or represents 1-(4-chlorophenyl)pyrazol-3-yl or represents 1,2-propanedione-bis(O-methyloxim)-1-yl, 
         R 21  represents hydrogen or fluorine. 
       
     
   
   
       2 . Active compound combinations according to  claim 1 , wherein Z represents the radical Z3 below: 
     
       
         
         
             
             
         
       
       wherein R 22  represents hydrogen or C 1-4 -alkyl. 
     
   
   
       3 . Active compound combinations according to any one of  claims 1  or  2 , wherein Y represents the radical Y5 below: 
     
       
         
         
             
             
         
       
       wherein m is an integer from 1 to 4 and 
       R 23  and R 24  represent fluorine, chlorine, bromine, difluoromethyl or trifluormethyl. 
     
   
   
       4 . Active compound combinations according to any one of  claims 1  to  3 , comprising a carboxamide of the formula (I) selected from the group consisting of
 (I-1) N-[2-(1,3-dimethylbutyl)phenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (I-3) N-[2-(1,3-dimethylbutyl)phenyl]-5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (14) 3-difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, (I-5) 3-(trifluoromethyl)-N-[2-1,3-dimethylbutyl)phenyl]-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (I-6) 3-(trifluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-5-chloro-1-methyl-1H-pyrazole-4-carboxamide, (I-7) 1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-8) 5-fluoro-1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-9) 3-(difluoromethyl)-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-10) 3-(trifluoromethyl)-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-11) 3-(trifluoromethyl)-5-fluoro-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-12) 3-(trifluoromethyl)-5-chloro-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide, (I-13) N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide, (I-14) 2-iodine-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, (I-15) N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide, (I-16) 2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide, (I-17) 2-chloro-N-(1,1,3-trimethylindan-4-yl)nicotinamide, (I-18) boscalid, (I-19) furametpyr, (I-20) N-(3-p-tolylthiophen-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, (I-21) penthiopyrad, (I-22) N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide, (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (I-24) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide, (I-25) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide, (I-26) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-arboxamide, (I-27) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide, (I-28) N-4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide, (I-29) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide, (I-30) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (I-31) N-(4′-iodine-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide, (I-32) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(difluoromethyl)-,3-thiazole-5-carboxamide.   
   
   
       5 . Active compound combinations according to any one of  claims 1  to  4 , comprising at least one azole of the formula (II) selected from the group consisting of
 (II-1) azaconazole, (II-2) etaconazole, (II-3) propiconazole, (II-4) difenoconazole, (II-5) bromuconazole, (II-6) cyproconazole, (II-7) hexaconazole, (II-8) penconazole, (II-9) myclobutanil, (II-10) tetraconazole, (II-11) flutriafol, (II-12) epoxiconazole, (II-13) flusilazole, (II-14) simeconazole, (II-15) prothioconazole, (II-16) fenbuconazole, (II-17) tebuconazole, (II-18) ipconazole, (II-19) metconazole, (II-20) triticonazole, (II-21) bitertanol, (II-22) triadimenol, (II-23) triadimefon, (II-24) fluquinconazole, (II-25) quinconazole.   
   
   
       6 . Active compound combinations according to any one of  claims 1  to  5  comprising a strobilurin of the formula (III) selected from the group consisting of
 (III-1) azoxystrobin, (III-2) fluoxastrobin, (III-3) (2E)-2-(2-{[6-3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide, (1H-4) trifloxystrobin, (III-5) (2E)-2-(methoxyimino)-N-methyl-2-2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]-ethylidene}amino)oxy]methyl}phenyl)ethanamide, (III-6) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide, (III-7) orysastrobin, (III-8) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}-amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (III-9) kresoxim-methyl, (III-10) dimoxystrobin, (III-11) picoxystrobin, (III-12) pyraclostrobin, (III-13) metominostrobin.   
   
   
       7 . Active compound combinations according to any one of  claims 1  to  6  selected from the group consisting of 
     2.1 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-24) fluquinconazole, (III-2) fluoxastrobin 
     2.2 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (III-22) triadimenol, (III-2) fluoxastrobin 
     2.3 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, II-24) fluquinconazole, (II-22) triadimenol 
     2.4 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-18) ipconazole, (III-4) trifloxystrobin 
     2.5 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (II-15) prothioconazole 
     2.6 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (II-17) tebuconazole 
     2.7 (I-2) N-[2-1 ,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (III-2) fluoxastrobin 
     2.8 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (III-4) trifloxystrobin 
     2.9 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (II-17) tebuconazole 
     2.10 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (III-2) fluoxastrobin 
     2.11 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (III-4) trifloxystrobin 
     2.12 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-17) tebuconazole, (III-2) fluoxastrobin 
     2.13 (I-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (II-17) tebuconazole, (III-4) trifloxystrobin 
     2.14 (I-18) boscalid, (II-11) flutriafol, (II-15) prothioconazole 
     2.15 (I-18) boscalid, (II-11) flutriafol, (II-17) tebuconazole 
     2.16 (I-18) boscalid, (II-11) flutriafol, (III-2) fluoxastrobin 
     2.17 (I-18) boscalid, (II-11) flutriafol, (III-4) trifloxystrobin 
     2.18 (I-18) boscalid, (II-15) prothioconazole, (II-17) tebuconazole 
     2.19 (I-18) boscalid, (II-15) prothioconazole, (III-2) fluoxastrobin 
     2.20 (I-18) boscalid, (II-15) prothioconazole, (III-4) trifloxystrobin 
     2.21 (I-18) boscalid, (II-17) tebuconazole, (III-2) fluoxastrobin 
     2.22 (I-18) boscalid, (II-17) tebuconazole, (III-4) trifloxystrobin 
     2.23 (I-21) penthiopyrad, (II-11) flutriafol, (II-15) prothioconazole 
     2.24 (I-21) penthiopyrad, (II-11) flutriafol, (II-17) tebuconazole 
     2.25 (I-21) penthiopyrad, (II-11) flutriafol, (II-2) fluoxastrobin 
     2.26 (I-21) penthiopyrad, (II-11) flutriafol, (III-4) trifloxystrobin 
     2.27 (I-21) penthiopyrad, (II-15) prothioconazole, (II-17) tebuconazole 
     2.28 (I-21) penthiopyrad, (II-15) prothioconazole, (III-2) fluoxastrobin 
     2.29 (I-21) penthiopyrad, (II-15) prothioconazole, (III-4) trifloxystrobin 
     2.30 (I-21) penthiopyrad, (II-17) tebuconazole, (III-2) fluoxastrobin 
     2.31 (I-21) penthiopyrad, (II-17) tebuconazole, (III-4) trifloxystrobin 
     2.32 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (II-15) prothioconazole 
     2.33 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (II-17) tebuconazole 
     2.34 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (III-2) fluoxastrobin 
     2.35 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-11) flutriafol, (III-4) trifloxystrobin 
     2.36 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (II-17) tebuconazole 
     2.37 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (III-2) fluoxastrobin 
     2.38 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-15) prothioconazole, (III-4) trifloxystrobin 
     2.39 (I-23) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-17) tebuconazole, (III-2) fluoxastrobin 
     2.40 (I-23) N-(3′,4′-dichloro-5-fluoro-, 1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (II-17) tebuconazole, (III-4) trifloxystrobin. 
   
   
       8 . Use of active compound combinations according to any one of  claims 1  to  7  for controlling unwanted phytopathogenic fungi. 
   
   
       9 . Use of active compound combinations according to any one of  claims 1  to  7  for treating seed. 
   
   
       10 . Use of active compound combinations according to any one of  claims 1  to  7  for treating transgenic plants. 
   
   
       11 . Use of active compound combinations according to any one of  claims 1  to  7  for treating seed of transgenic plants. 
   
   
       12 . Seed which has been treated with an active compound combination according to any one of  claims 1  to  7 . 
   
   
       13 . Use of seed which has been treated with an active compound combination according to any one of  claims 1  to  7  for controlling unwanted phytopathogenic fungi. 
   
   
       14 . Method for controlling unwanted phytopathogenic fungi, characterized in that active compound combinations according to any one of  claims 1  to  7  are applied to the unwanted phytopathogenic fungi and/or their habitat and/or seed. 
   
   
       15 . Process for preparing fungicidal compositions, characterized in that active compound combinations according to any one of  claims 1  to  7  are mixed with extenders and/or surfactants.