Fungicidal Mixtures Comprising Substituted 1-methylpyrazol-4-ylcarboxanilides

Abstract

Fungicidal mixtures, comprising as active components 1) at least one 1-methylpyrazol-4-ylcarboxanilide of the formula I where R 1 ═C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, R 2 =hydrogen or halogen, X=hydrogen or halogen, Q=direct bond, a cyclopropylene or an anellated bicyclo[2.2.1]heptane ring; R 3 ═C 1 -C 6 -alkyl, cyclopropyl or phenyl substituted with two or three halogen atoms or a trifluoromethylthio radical; and 2) at least one active compound II, selected from the active compound groups A) to K): A) organo(thio)phosphates; B) carbamates; C) pyrethroids; D) growth regulators; E) GABA antagonist compounds; F) macrocyclic lactone insecticides; G) METI I acaricides; H) METI II and III compounds; J) oxidative phosphorylation inhibitor compounds; K) various compounds; in a synergistically effective amount, methods for controlling harmful fungi using mixtures of at least one compound I and at least one active compound II, the use of a compound I or compounds I with active compounds II for preparing such mixtures, and also compositions and seed comprising such mixtures.

1 . A mixture for controlling phytopathogenic harmful fungi comprising, as active components,
 1) at least one 1-methylpyrazol-4-ylcarboxanilide of the formula I   
       
         
           
           
               
               
           
         
         in which the substituents are as defined below: 
         R 1  is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
         R 2  is hydrogen or halogen; 
         X is hydrogen or fluorine; 
         Q is a direct bond; 
         R 3  is phenyl substituted with two or three halogen atoms; 
         and 
         2) at least one active compound II, selected from the active compound groups A) to K): 
         A) an organo(thio)phosphate selected from the group consisting of acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxy-demeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos and trichlorfon; 
         B) a carbamate selected from the group consisting of: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb and triazamate; 
         D) a growth regulator selected from the group consisting of the following 
       
       a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, -flucycloxuron, hexaflumuron, lufenuron, novaluron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole and clofentazine; 
       b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, and azadirachtin; 
       c) juvenoids: pyriproxyfen, methoprene and fenoxycarb; 
       d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen and spirotetramat;
 E) a GABA antagonist compound selected from the group consisting of endosulfan, ethiprole, vaniliprole, pyrafluprole, pyriprole and the phenylpyrazole of the formula E 1   
 
       
         
           
           
               
               
           
         
         F) a macrocyclic lactone insecticide selected from the group consisting of abamectin, emamectin, milbemectin, lepimectin, spinosad and spinetoram; 
         G) a METI I acaricide selected from the group consisting of fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad and flufenerim 
         H) a METI II and III compound selected from the group consisting of acequinocyl, fluacyprim and hydramethylnon; 
         an oxidative phosphorylation inhibitor compound selected from the group consisting of cyhexatin, diafenthiuron, fenbutatin oxide and propargite; 
         a compound selected from the group consisting of amidoflumet, benclothiaz, bifenazate, bistrifluron, cartap, chlorfenapyr, cryomazine, cyazypyr (HGW86), cyenopyrafen, cyflumetofen, flonicamid, flubendiamide, flupyrazofos, imicyafos, indoxacarb, metaflumizone, piperonyl butoxide, pymetrozine, pyridalyl, pyrifluquinazon, thiocyclam and the thiazole compound of formula K 1   
       
       
         
           
           
               
               
           
         
         in a synergistically effective amount. 
       
     
     
         2 . The fungicidal mixture of  claim 1 , comprising as component 1) a 1-methylpyrazol-4-ylcarboxanilide of the formula I where R 1  is C 1 -C 4 -haloalkyl, R 2  is hydrogen, Q is a direct bond and R 3  is phenyl substituted by two or three halogen atoms. 
     
     
         3 .- 4 . (canceled) 
     
     
         5 . The fungicidal mixture of  claim 1 , comprising as component 1) a 1-methylpyrazol-4-ylcarboxanilide of the formula I where R 1  is C 1 -C 4 -alkyl, R 2  is halogen, X is hydrogen, Q is a direct bond, and R 3  is C 1 -C 6 -alkyl. 
     
     
         6 . The fungicidal mixture of  claim 1 , comprising an additional active compound. 
     
     
         7 . The fungicidal mixture of  claim 1 , comprising the components 1) and 2) in a weight ratio of from 100:1 to 1:100. 
     
     
         8 . A composition, comprising at least one liquid or solid carrier and the mixture of  claim 1 . 
     
     
         9 . A method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or plants to be protected against fungal attack, the soil, seed, areas, materials or spaces with an effective amount of at least one component 1) and at least one component 2) 
       1) a compound of formula I 
       
         
           
           
               
               
           
         
         in which the substituents are as defined below: 
         R 1  is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
         R 2  is hydrogen or halogen; 
         X is hydrogen or fluorine; 
         Q is a direct bond; 
         R 3  is phenyl substituted with two or three halogen atoms; 
         and 
       
       2) a compound II, selected from the active compound groups A) to K):
 A) an organo(thio)phosphate selected from the group consisting of acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxy-demeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos and trichlorfon; 
 B) a carbamate selected from the group consisting of: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb and triazamate; 
 D) a growth regulator selected from the group consisting of the following 
 
       a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, -flucycloxuron, hexaflumuron, lufenuron, novaluron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole and clofentazine; 
       b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, and azadirachtin; 
       c) juvenoids: pyriproxyfen, methoprene and fenoxycarb; 
       d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen and spirotetramat;
 E) a GABA antagonist compound selected from the group consisting of endosulfan, ethiprole, vaniliprole, pyrafluprole, pyriprole and the phenylpyrazole of the formula E 1   
 
       
         
           
           
               
               
           
         
         F) a macrocyclic lactone insecticide selected from the group consisting of abamectin, emamectin, milbemectin, lepimectin, spinosad and spinetoram; 
         G) a METI I acaricide selected from the group consisting of fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad and flufenerim 
         H) a METI II and III compound selected from the group consisting of acequinocyl, fluacyprim and hydramethylnon; 
         an oxidative phosphorylation inhibitor compound selected from the group consisting of cyhexatin, diafenthiuron, fenbutatin oxide and propargite; 
         a compound selected from the group consisting of amidoflumet, benclothiaz, bifenazate, bistrifluron, cartap, chlorfenapyr, cryomazine, cyazypyr (HGW86), cyenopyrafen, cyflumetofen, flonicamid, flubendiamide, flupyrazofos, imicyafos, indoxacarb, metaflumizone, piperonyl butoxide, pymetrozine, pyridalyl, pyrifluquinazon, thiocyclam and the thiazole compound of formula K 1   
       
       
         
           
           
               
               
           
         
         in a synergistically effective amount. 
       
     
     
         10 . The method according to  claim 9 , wherein the components 1) and 2) are applied simultaneously as individual components or as a mixture, separately, or in succession. 
     
     
         11 . The method according to  claim 10 , wherein the components 1) and 2) are applied in an amount of from 5 g/ha to 2000 g/ha. 
     
     
         12 . The method according to  claim 10 , wherein the components 1) and 2) are applied in an amount of from 1 g to 1000 g per 100 kg of seed. 
     
     
         13 . The method of  claim 9 , wherein component 1) is a 1-methylpyrazol-4-ylcarboxanilide of the formula I where R 1  is C 1 -C 4 -haloalkyl, R 2  is hydrogen, Q is a direct bond and R 3  is phenyl substituted by two or three halogen atoms. 
     
     
         14 .- 15 . (canceled) 
     
     
         16 . The method of  claim 9 , wherein component 1) is a 1-methylpyrazol-4-ylcarboxanilide of the formula I where R 1  is C 1 -C 4 -alkyl, R 2  is halogen, X is hydrogen, Q is a direct bond, and R 3  is C 1 -C 6 -alkyl. 
     
     
         17 . A seed, of treated with the mixture  claim 1  in an amount of from 1 g to 1000 g per 100 kg of seed. 
     
     
         18 . The fungicidal mixture of  claim 1 , wherein the active compound II is a macrocyclic lactone insecticide selected from the group consisting of abamectin, emamectin, milbemectin, lepimectin, spinosad and spinetoram. 
     
     
         19 . The method of  claim 9 , wherein the active compound II is a macrocyclic lactone insecticide selected from the group consisting of abamectin, emamectin, milbemectin, lepimectin, spinosad and spinetoram.