Pesticidal mixtures comprising a pyrazole compound

Abstract

The present invention relates to pesticidal mixtures comprising as active compounds 1) at least one pyrazole compound A selected from the compounds of formula I: wherein the variables have the meaning as defined in the description, and 2) at least one further compound B selected from the compounds of the following groups A.1, A.2, A.3, A.4, A.5, A.6, A.7, A.8, A.9, A.10, A.11, A.12, A.13, A.14, A.15, A.16, A.17, F.1, F.2, F.3, F.4, F.5, F.6, F.7, F.8, F.9, F.10 and F.11 as defined in the specification. The present invention also relates to novel pyrazole compounds of the formula I. The present invention also relates to methods and use of these mixtures and novel compounds for combating invertebrate pests such as insects, arachnids or nematodes in and on plants, and for protecting such plants being infested with pests, especially also for protecting plant propagation material as like seeds.

1 . (canceled) 
     
     
         2 . A pesticidal mixture comprising as active compounds
 1) at least one pyrazole compound A selected from the compound of formula I:   
       
         
           
           
               
               
           
         
         wherein 
         R 1  is H, C 1 -C 2 -alkyl, or C 1 -C 2 -alkoxymethyl; 
         R 2  is CH 3 , CHF 2 , or CF 3 ; 
         R 3  is selected from CN, C 2 H 5 , CH(CH 3 ) 2 , CHF 2 , CH 2 F, CF 3 , CH 2 OCH 3 , c-C 3 H 5 , 1-F-c-C 3 H 4 , 1-CN-c-C 3 H 4 , 1-CH 3 -c-C 3 H 4 , 1-OCH 3 -c-C 3 H 4 , 1-CF 3 -c-C 3 H 4 , 1-OCF 3 -c-C 3 H 4 , 1-SCH 3 -c-C 3 H 4 , 1-SCF 3 -c-C 3 H 4 , C(CH 3 ) 3 , CF(CH 3 ) 2 , C(CN)(CH 3 ) 2 , C(OCH 3 )(CH 3 ) 2 , C(OCF 3 )(CH 3 ) 2 , C(SCH 3 )(CH 3 ) 2 , C(SCF 3 )(CH 3 ) 2 , C(CH 3 ) 2 CF 3 , CHFCH 3 , CH(CN)CH 3 , CF 2 CH 3 , C(OCH 3 ) 2 CH 3 , CH(OCH 3 )CH 3 , CH(OCF 3 )CH 3 , CH(SCH 3 )CH 3 , CH(SCF 3 )CH 3 , CH(CH 3 )CF 3 , CH 2 SCH 3 , CH 2 SCF 3 , CH 2 OCF 3 , CH 2 CN, and CH 2 CF 3 ; 
         R 4  is CH 3 , C 2 H 5 , CHF 2 , or CF 3 ; 
         R 5  is H, F, CN, CH 3 , OCH 3 , SCH 3 , CF 3 , OCF 3 , or SCF 3 ; 
         the stereoisomers, salts, tautomers and N-oxides thereof; and 
         2) at least one further compound B selected from the compounds of the following groups A.2, A.3, A.4, A.5, A.8, A.10, A.13, A.17, F.1, F.2, F.3, F.4, F.6, F.7, and F.8:
 A.2 Pyrethroid compounds, selected from the group consisting of acrinathrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, tau-fluvalinate, silafluofen, tralomethrin; 
 A.3 Nicotinic receptor agonists/antagonists compounds, selected from the group consisting of acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam and thiosultap-sodium; 
 A.4 GABA gated chloride channel antagonist compounds, selected from the group consisting of ethiprole and fipronil; 
 A.5 Chloride channel activators, selected from the group consisting of abamectin, emamectin benzoate, and lepimectin; 
 A.8 Selective feeding blockers, selected from the group consisting of pymetrozine and flonicamid; 
 A.10 Lipid biosynthesis inhibitors, selected from the group consisting of spiromesifen and spirotetramat; 
 A.13 Anthranilamide compounds, selected from the group consisting of chloranthraniliprole, cyantraniliprole; 
 A.17 Various compounds, selected from the group consisting of pyrifluquinazon, sulfoxaflor, and afidopyropen; 
 F.1 Respiration inhibitors selected from the following groups a), b), c) and d): 
 a) Inhibitors of complex III at Qo site (e.g. strobilurins), selected from the group consisting of azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin; 
 c) inhibitors of complex II (e.g. carboxamides), selected from the group consisting of boscalid, fluopyram, fluxapyroxad, penthiopyrad, and sedaxane; 
 d) other respiration inhibitors (e.g. complex I, uncouplers), selected from the group consisting of ametoctradin; and silthiofam; 
 F.2 Sterol biosynthesis inhibitors (SBI fungicides) selected from the following groups a), b) and c): 
 a) C14 demethylase inhibitors (DMI fungicides), selected from the group consisting of the following triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole and uniconazole; the following imidazoles: imazalil, pefurazoate, prochloraz and triflumizol; and the following pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox and triforine; 
 c) Inhibitors of 3-keto reductase: fenhexamid; 
 F.3 Nucleic acid synthesis inhibitors selected from the following groups a) and b): 
 a) phenylamides or acyl amino acid fungicides, selected from the group consisting of metalaxyl, and metalaxyl-M (mefenoxam); 
 F.4 Inhibitors of cell division and cytoskeleton selected from the following groups a) and b): 
 a) tubulin inhibitors, selected from the group consisting of benzimidazoles or thiophanates such as benomyl, carbendazim, fuberidazole, thiabendazole or thiophanate-methyl; and triazolopyrimidines such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 
 F.6 Signal transduction inhibitors selected from the following group: MAP/histidine kinase inhibitors, selected from the group consisting of fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil and fludioxonil; 
 F.7 Lipid and membrane synthesis inhibitors selected from the following group: compounds affecting phospholipid biosynthesis and cell wall deposition, selected from the group consisting of dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester; 
 F.8 Inhibitors with multi-site action selected from the following groups b), c) and d): 
 b) thio- and dithiocarbamates selected from the group consisting of ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb and ziram; 
 c) organochlorine compound chlorothalonil; 
 d) guanidines and others selected from the group consisting of guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate) and dithianon; 
 
         comprising the pyrazole compound A and the active compound B in a weight ratio of from 500:1 to 1:100, 
       
       except for pesticidal mixtures comprising a pyrazole compound of formula I, wherein 
       R 1  is H, CH 3 , C 2 H 5 , or CH 2 OCH 3 ; 
       R 2  is CH 3 , CHF 2 , or CF 3 ; 
       R 3  is CF 3 , or c-C 3 H 5 ; 
       R 4  is CH 3 ; and 
       R 5  is H. 
     
     
         3 . The mixture of  claim 2 , where in formula I the variable R 1  is CH 3 , or C 2 H 5 . 
     
     
         4 . The mixture of  claim 2 , wherein the compound of formula I the variables R 3 ,
 R 4  and R 5  have the following meanings:   R 3  is CN, CH(CH 3 ) 2 , CHF 2 , CH 2 OCH 3 , cyclopropyl, 1-F-cyclopropyl or 1-CN-cyclopropyl,   R 4  is CHF 2 ,   R 5  is H, or CH 3 ;
 stereoisomers, salts, tautomers and N-oxides thereof. 
   
     
     
         5 . The mixture of  claim 2 , wherein the compound of formula I the variables R 1 , R 2 , R 3 , R 4  and R 5  have the following meanings:
 R 1  is CH 3  or C 2 H 5 ;   R 2  is CH 3 ;   R 3  is CH(CH 3 ) 2 , CHF 2 , 1-CN-c-C 3 H 4 , CH 2 CHF 2 , CH 2 CF 3 , C(CN)(CH 3 ) 2 , or CHFCH 3 ;   R 4  is CH 3 , and   R 5  is H or CN.   
     
     
         6 . The mixture of  claim 2 , where the compound of formula I is selected from the compounds of the following table: 
       
         
           
                 
                 
                 
                 
                 
                 
               
                     
                 
                   No. 
                   R 1   
                   R 2   
                   R 3   
                   R 4   
                   R 5   
                 
                     
                 
                   I-673 
                   CH 3   
                   CH 3   
                   CH(CH 3 ) 2   
                   CH 3   
                   H 
                 
                   I-674 
                   CH 2 CH 3   
                   CH 3   
                   CH(CH 3 ) 2   
                   CH 3   
                   H 
                 
                   I-680 
                   CH 2 CH 3   
                   CH 3   
                   CHF 2   
                   CH 3   
                   H 
                 
                   I-698 
                   CH 2 CH 3   
                   CH 3   
                   1-CN—c-C 3 H 4   
                   CH 3   
                   H 
                 
                     
                 
             
                
                
                
               
               
                
                
                
                
                
               
            
           
         
       
     
     
         7 . The mixture of  claim 2  comprising a compound of formula I and a compound B from the groups A.2 to A.17. 
     
     
         8 . The mixture of  claim 2  comprising a compound of formula I and a compound B from the groups F.1 to F.8. 
     
     
         9 . The mixture of  claim 2 , wherein at least one active compound B is selected from the group consisting of acrinathrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, tau-fluvalinate, silafluofen, tralomethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, thiacloprid, ethiprole, fipronil, abamectin, emamectin benzoate, lepimectin, flonicamid, pymetrozine; spiromesifen, spirotetramat, chloranthraniliprole, cyantraniliprole, pyrifluquinazon, sulfoxaflor, afidopyropen, azoxystrobin, pyraclostrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, boscalid, fluopyram, fluxapyroxad, penthiopyrad, sedaxane, silthiofam, ametoctradin, difenoconazol, epoxiconazole, fluquinconazole, ipconazole, prothioconazole, tebuconazole, triticonazole, prochloraz, fenhexamid, metalaxyl, metalaxyl-M, carbendazim, thiophanate-methyl, iprodione, iprovalicarb, thiram, benthiavalicarb, mancozeb, and chlorothalonil. 
     
     
         10 . The mixture of  claim 2 , wherein the at least one active compound B is selected from fipronil, alpha-cypermethrin, thiamethoxam, abamectin, spirotetramat, imidacloprid, flonicamid, chloranthraniliprole, pymetrozine, sulfoxaflor and afidopyropen. 
     
     
         11 . The mixture of  claim 2 , wherein the at least one active compound B is selected from azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, fluxapyroxad, benthiavalicarb, iprovalicarb, fenhexamid, boscalid, mancozeb, ametoctradin, metalalxyl-m, carbendazim, iprodione, prochloraz, chlorothalonil, penthiopyrad, difenoconazole, epoxiconazole, ipconazole, prothioconazole and tebuconazole. 
     
     
         12 . A composition comprising a pesticidal mixture according to  claim 2  and at least one inert liquid and/or solid carrier. 
     
     
         13 . An agricultural composition for combating animal pests comprising a pesticidal mixture according to  claim 2  and at least one inert liquid and/or solid acceptable carrier and, if desired, at least one surfactant. 
     
     
         14 . A method for combating or controlling invertebrate pests comprising contacting the pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of a pesticidal mixture according to  claim 2 . 
     
     
         15 . A method for protecting growing plants or plant propagation materials from attack or infestation by invertebrate pests comprising contacting a plant, a plant propagation material or soil or water in which the plant is growing, with a pesticidally effective amount of a pesticidal mixture according to  claim 2 . 
     
     
         16 . Plant propagation material comprising a pesticidal mixture according to  claim 2  in an amount of from 0.1 g to 10 kg per 100 kg of seed. 
     
     
         17 . A method for protection of plant propagation material comprising contacting the plant propagation material with a pesticidal mixture according to  claim 2  in an amount of from 0.1 g to 10 kg per 100 kg of plant propagation material. 
     
     
         18 . A method for controlling phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a pesticidal mixture according to  claim 2 , wherein the at least one further compound B selected from the compounds of the groups F.1, F.2, F.3, F.4, F.6, F.7, and F.8. 
     
     
         19 . A method for protecting plants from phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a pesticidal mixture according to  claim 2 , wherein the at least one further compound B selected from the compounds of the groups F.1, F.2, F.3, F.4, F.6, F.7, and F.8.