Mixtures of strobilurins with 1-methylcyclopropene

Abstract

The present invention relates to mixtures comprising a) a compound of the formula I in which X, m, Q and a are as defined in the description and b) one or more ethylene modulators (II) selected from the group consisting of: inhibitors of ethylene biosynthesis which inhibit the conversion of S-adenosyl-L-methionine into 1-aminocyclopropane-1-carboxylic acid (ACC), inhibitors of ethylene biosynthesis which block the conversion of ACC into ethylene, or inhibitors of ethylene action, and also to compositions comprising them and to their use for controlling harmful fungi.

1 - 18 . (canceled) 
     
     
         19 . A mixture, comprising
 a) a compound of the formula I   
       
         
           
           
               
               
           
         
         in which 
         X is halogen, C 1 -C 4 -alkyl or trifluoromethyl; 
         m is 0 or 1; 
         Q is C(═CH—CH 3 )—COOCH 3 , C(═CH—OCH 3 )—COOCH 3 , C(═N—OCH 3 )—CONHCH 3 , C(═N—OCH 3 )—COOCH 3  or N(—OCH 3 )—COOCH 3 ; 
         A is —O—B, —CH 2 O—B, —OCH 2 —B, —CH═CH—B, —CH 2 O—N═C(R 1 )—B or —CH 2 O—N═C(R′)—C(R 2 )═N—OR 3 , where
 B is phenyl, naphthyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl which contains one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, where the ring systems are unsubstituted or substituted by one to three radicals R a :
 R a  is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkyloxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -allylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, 
 C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NOR′)—OR″ or OC(R′) 2 —C(R″)═NOR″, 
 where the cyclic radicals for their part are unsubstituted or substituted by one to three radicals R b : 
 R b  is cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(═NOR′)—OR″; 
 R′ is hydrogen, cyano, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 4 -haloalkyl; 
 R″ is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -haloalkenyl or C 3 -C 6 -haloalkinyl; 
 
 R 1  is hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 1 -C 4 -alkoxy; 
 R 2  is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered hetaryl, 5- or 6-membered hetarylcarbonyl or 5- or 6-membered hetarylsulfonyl, where the ring systems are unsubstituted or substituted by one to three radicals R a ,
 is C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkinyl, C 1 -C 10 -alkylcarbonyl, C 2 -C 10 -alkenylcarbonyl, C 3 -C 10 -alkinylcarbonyl, C 1 -C 10 -alkylsulfonyl or C(R′)═NOR″, where the hydrocarbon radicals of these groups are unsubstituted or substituted by one to three radicals R c : 
 R c  is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or hetarylthio, where the cyclic groups for their part may be partially of fully halogenated or may carry one to three radicals R a ; and 
 
 R 3  is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl, where the hydrocarbon radicals of these groups may be unsubstituted or substituted by one to three radicals R c ; and 
 
         b) 1-methylcyclopropene; 
         in a weight ratio of I to 1-methylcyclopropene of from 20:1 to 0.05:1 
       
     
     
         20 . The mixture of  claim 19  where the compound of the formula I is a strobilurin derivative selected from the group consisting of azoxystrobin, dimoxy-strobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, trifloxy-strobin, picoxystrobin or pyraclostrobin. 
     
     
         21 . The mixture of  claim 19  where the compound of the formula I is pyraclostrobin. 
     
     
         22 . The mixture of  claim 19  wherein 1-methylcyclopropene is selected as ethylene modulator (II). 
     
     
         23 . The mixture of  claim 19  which additionally comprises an azole III selected from the group consisting of bromoconazole, cyproconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, metconazole, myclobutanil, propiconazole, prochloraz, prothioconazole, tebuconazole and triticonazole. 
     
     
         24 . The mixture of  claim 19  which additionally comprises a surfactant selected from the group consisting of: polyoxyethylene sorbitan monolaurate, alkylphenoxy polyethoxy ethanol, fatty alcohol, fatty alcohol alkoxylate and sodium dodecylsulfate. 
     
     
         25 . A method for controlling rust infections in legumes, which comprises treating the above-ground plant parts of the legumes with an aqueous formulation of a mixture as claimed in  claim 19 . 
     
     
         26 . The method of  claim 25 , wherein rust infection on leaves and fruits of soya plants is controlled. 
     
     
         27 . The method of  claim 26 , wherein the rust infection is caused by  Phakopsora pachyrhizi  and/or  Phakopsora meibomiae.    
     
     
         28 . The method of  claim 25 , wherein the compound of the formula I is a strobilurin derivative selected from the group consisting of azoxystrobin, dimoxy-strobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, trifloxy-strobin, picoxystrobin or pyraclostrobin. 
     
     
         29 . The method of  claim 28 , wherein the compound of the formula I is pyraclostrobin. 
     
     
         30 . The method of  claim 29 , wherein 1-methylcyclopropene is selected as ethylene modulator (II). 
     
     
         31 . The method of  claim 30 , wherein the mixture additionally comprises an azole III selected from the group consisting of bromoconazole, cyproconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, metconazole, myclobutanil, propiconazole, prochloraz, prothioconazole, tebuconazole or triticonazole. 
     
     
         32 . The method of  claim 31 , wherein the mixture additionally comprises a surfactant selected from the group consisting of: polyoxyethylene sorbitan monolaurate, alkylphenoxy polyethoxy ethanol, fatty alcohol, fatty alcohol alkoxylate and sodium dodecylsulfate. 
     
     
         33 . A method for increasing the yield and quality of legumes comprising treating the above-ground plant parts of the legumes with an aqueous formulation of the mixtures as claimed in  claim 19 . 
     
     
         34 . A method for reducing the ethylene evolution of plants by applying an effective amount of a mixture as claimed in  claim 19 . 
     
     
         35 . The method of  claim 34 , wherein the compound of the formula I is a strobilurin derivative selected from the group consisting of azoxystrobin, dimoxy-strobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, trifloxy-strobin, picoxystrobin or pyraclostrobin. 
     
     
         36 . The method of  claim 35 , wherein the compound of the formula I is pyraclostrobin. 
     
     
         37 . The method of  claim 36 , wherein 1-methylcyclopropene is selected as ethylene modulator (II). 
     
     
         38 . A method for reducing undesired defoliation of crop plants by applying an effective amount of a mixture as claimed in  claim 19 .