Fungicidal Mixtures Based on Azolopyrimidinylamines

Abstract

Fungicidal mixtures comprising, as active components, 1) azolopyrimidinylamines of the formula I, in which the substituents are as defined in the description and 2) at least one active compound II selected from the following groups: azoles, strobilurins, carboxamides, heterocylic compounds, carbamates and other active compounds selected from the group consisting of guanidines, antibiotics, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, inorganic active compounds, growth retardants and cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone and spiroxamine; in a synergistically effective amount. Methods for controlling harmful fungi using mixtures of the compound I with active compounds II and the use of the compound I with active compounds II for preparing such mixtures, and also compositions comprising these mixtures.

1 . A fungicidal mixture comprising, as active components:
 1) an azolopyrimidinylamine of formula I   
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is C 3 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 5 -C 12 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl; 
         R 2  is C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
 where the aliphatic chains in R 1  and/or R 2  may be substituted by one to four identical or different groups R a : 
 R a  is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or NR A R B ;
 R A , R B  are hydrogen and C 1 -C 6 -alkyl; 
 
 where the cyclic groups in R 1  and/or R a  may be substituted by one to four groups R b : 
 R b  is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , C 1 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy; 
 
         R 3  is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C 1 -C 6 -alkyl-S(O) m —;
 m is 0, 1 or 2; 
 
         A is CR 3  or N; 
       
       and
 2) at least one active compound II selected from the group consisting of: 
 A) bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; 
 B) azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; 
 C) carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, dimethomorph, flumorph; flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid; N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethanesulfonylamino-3-methylbutyramide; 
 D) fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil triforine, fenpiclonil, fludioxonil aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, amisulbrom, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-5-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; 
 E) mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, and methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate; 
 
       and
 F) dodine, iminoctadine, guazatine;
 kasugamycin, streptomycin, polyoxine, validamycin A; 
 binapacryl, dinocap, dinobuton; 
 dithianon, isoprothiolane; 
 fentin salts; 
 edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; 
 chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid; 
 Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine; 
 prohexadione and its salts, trinexapac-ethyl, chlormequat, mepiquat-chloride, diflufenzopyr; 
 
 
       wherein the azolopyrimidinylamine of formula I and the at least one active compound II of the mixture are present in a synergistically effective amount. 
     
     
         2 . The fungicidal mixture of  claim 1 , wherein the weight ratio of the azolopyrimidinylamine of formula I and the at least one active compound of formula II is from 100:1 to 1:100. 
     
     
         3 . The fungicidal mixture of  claim 1 , wherein the azolopyrimidinylamine of formula I is of the formula IA 
       
         
           
           
               
               
           
         
         wherein
 R 1  is C 3 -C 12 -alkyl, C 5 -C 12 -alkoxyalkyl, phenyl or phenyl-C 1 -C 4 -alkyl, where phenyl may be substituted by one to three groups R b ; 
 R 2  is C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 R 3  is hydrogen or NH 2 . 
 
       
     
     
         4 . The fungicidal mixture of  claim 1 , wherein the azolopyrimidinylamine of formula I is selected from the group consisting of
 6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-trifluormethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine and   5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine.   
     
     
         5 . The fungicidal mixture of  claim 1 , wherein the at least one active compound II is selected from the group A, C or E. 
     
     
         6 . The fungicidal mixture of  claim 1 , wherein the at least one active compound II is selected from the group B, D or F. 
     
     
         7 . The fungicidal mixture of  claim 1 , wherein the mixture comprises the azolopyrimidinylamine of formula I and two active compounds II, wherein each active compound II is independently selected from the group A, B, C, D, E or F. 
     
     
         8 . A composition comprising
 a liquid or solid carrier; and   a mixture of
 1) an azolopyrimidinylamine of formula I 
   
       
         
           
           
               
               
           
         
         
           wherein: 
           R 1  is C 3 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 5 -C 12 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl; 
           R 2  is C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
 where the aliphatic chains in R 1  and/or R 2  may be substituted by one to four identical or different groups R a : 
 R a  is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or NR A R B ;
 R A , R B  are hydrogen and C 1 -C 6 -alkyl; 
 
 where the cyclic groups in R 1  and/or R a  may be substituted by one to four groups R b : 
 R b  is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , C 1 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy; 
 
           R 3  is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C 1 -C 6 -alkyl-S(O) m —;
 m is 0, 1 or 2; 
 
           A is CR 3  or N; 
         
         and
 2) at least one active compound II selected from the group consisting of: 
 A) bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; 
 B) azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; 
 C) carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, dimethomorph, flumorph; flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid; N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethanesulfonylamino-3-methylbutyramide; 
 D) fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil triforine, fenpiclonil, fludioxonil aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, amisulbrom, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-5-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; 
 E) mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, and methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate; 
 
         and
 F) dodine, iminoctadine, guazatine; 
 kasugamycin, streptomycin, polyoxine, validamycin A; 
 binapacryl, dinocap, dinobuton; 
 dithianon, isoprothiolane; 
 fentin salts; 
 edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; 
 chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid; 
 Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine; 
 prohexadione and its salts, trinexapac-ethyl, chlormequat, mepiquat-chloride, diflufenzopyr; 
 
         wherein the azolopyrimidinylamine of formula I and the at least one active compound II of the mixture are present in a synergistically effective amount. 
       
     
     
         9 . The composition of  claim 8 , wherein the azolopyrimidinylamine of formula I is of the formula IA 
       
         
           
           
               
               
           
         
         wherein
 R 1  is C 3 -C 12 -alkyl, C 5 -C 12 -alkoxyalkyl, phenyl or phenyl-C 1 -C 4 -alkyl, where phenyl may be substituted by one to three groups R b ; 
 R 2  is C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 R 3  is hydrogen or NH 2 . 
 
       
     
     
         10 . The composition of  claim 8 , wherein the azolopyrimidinylamine of formula I is selected from the group consisting of
 6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-trifluormethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine and   5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine.   
     
     
         11 . The composition of  claim 8 , wherein the at least one active compound II is selected from the group A, C or E. 
     
     
         12 . The composition of  claim 8 , wherein the at least one active compound II is selected from the group B, D or F. 
     
     
         13 . The composition of  claim 8 , wherein the mixture comprises the azolopyrimidinylamine of formula I and two active compounds II, wherein each active compound II is independently selected from the group A, B, C, D, E or F. 
     
     
         14 . A method for controlling phytopathogenic harmful fungi comprising
 treating fungi, their habitat, or plants to be protected against fungal attack, soil or seed with an effective amount of
 1) an azolopyrimidinylamine of formula I 
   
       
         
           
           
               
               
           
         
         
           wherein: 
           R 1  is C 3 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 5 -C 12 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl; 
           R 2  is C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
 where the aliphatic chains in R 1  and/or R 2  may be substituted by one to four identical or different groups R a : 
 R a  is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or NR A R B ;
 R A , R B  are hydrogen and C 1 -C 6 -alkyl; 
 
 where the cyclic groups in R 1  and/or R a  may be substituted by one to four groups R b : 
 R b  is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , C 1 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy; 
 
           R 3  is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C 1 -C 6 -alkyl-S(O) m —;
 m is 0, 1 or 2; 
 
           A is CR 3  or N; 
         
         and
 2) at least one active compound II selected from the group consisting of: 
 A) bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; 
 B) azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; 
 C) carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, dimethomorph, flumorph; flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid; N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethanesulfonylamino-3-methylbutyramide; 
 D) fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil triforine, fenpiclonil, fludioxonil aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, amisulbrom, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-5-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; 
 E) mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, and methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate; 
 
         and
 F) dodine, iminoctadine, guazatine; 
 kasugamycin, streptomycin, polyoxine, validamycin A; 
 binapacryl, dinocap, dinobuton; 
 dithianon, isoprothiolane; 
 fentin salts; 
 edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; 
 chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid; 
 Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine; 
 prohexadione and its salts, trinexapac-ethyl, chlormequat, mepiquat-chloride, diflufenzopyr; 
 
         wherein the azolopyrimidinylamine of formula I and the at least one active compound II of the mixture are present in a synergistically effective amount; 
         wherein the phytopathogenic harmful fungi are controlled. 
       
     
     
         15 . The method of  claim 14 , wherein the weight ratio of the azolopyrimidinylamine of formula I and the at least one active compound of formula II is from 100:1 to 1:100. 
     
     
         16 . The method of  claim 14 , wherein the azolopyrimidinylamine of formula I is of the formula IA 
       
         
           
           
               
               
           
         
         wherein
 R 1  is C 3 -C 12 -alkyl, C 5 -C 12 -alkoxyalkyl, phenyl or phenyl-C 1 -C 4 -alkyl, where phenyl may be substituted by one to three groups R b ; 
 R 2  is C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 R 3  is hydrogen or NH 2 . 
 
       
     
     
         17 . The method of  claim 14 , wherein the azolopyrimidinylamine of formula I is selected from the group consisting of
 6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-trifluormethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine and   5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine.   
     
     
         18 . The method of  claim 14 , wherein the azolopyrimidinylamine of formula I and the at least one active compound II are applied simultaneously, separately, or in succession. 
     
     
         19 . The method of  claim 14 , wherein the azolopyrimidinylamine of formula I and the at least one active compound II are applied in an amount of from 5 g/ha to 2000 g/ha. 
     
     
         20 . The method of  claim 14 , wherein the azolopyrimidinylamine of formula I and the at least one active compound II are applied in an amount of from 1 g to 1000 g/100 kg of seed. 
     
     
         21 . The method of  claim 14 , wherein harmful fungi from the class of Oomycetes are controlled. 
     
     
         22 . Seed, comprising a mixture of
 1) an azolopyrimidinylamine of formula I   
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is C 3 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 5 -C 12 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl; 
         R 2  is C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
 where the aliphatic chains in R 1  and/or R 2  may be substituted by one to four identical or different groups R a : 
 R a  is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or NR A R B ;
 R A , R B  are hydrogen and C 1 -C 6 -alkyl; 
 
 where the cyclic groups in R 1  and/or R a  may be substituted by one to four groups R b : 
 R b  is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , C 1 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy; 
 
         R 3  is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C 1 -C 6 -alkyl-S(O) m —;
 m is 0, 1 or 2; 
 
         A is CR 3  or N; 
       
       and
 2) at least one active compound II selected from the group consisting of: 
 A) bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; 
 B) azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; 
 C) carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, dimethomorph, flumorph; flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid; N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethanesulfonylamino-3-methylbutyramide; 
 D) fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil triforine, fenpiclonil, fludioxonil aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, amisulbrom, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-5-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; 
 E) mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, and methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate; 
 
       and
 F) dodine, iminoctadine, guazatine; 
 kasugamycin, streptomycin, polyoxine, validamycin A; 
 binapacryl, dinocap, dinobuton; 
 dithianon, isoprothiolane; 
 fentin salts; 
 edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; 
 chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid; 
 Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine; 
 prohexadione and its salts, trinexapac-ethyl, chlormequat, mepiquat-chloride, diflufenzopyr; 
 
       wherein the azolopyrimidinylamine of formula I and the at least one active compound II of the mixture are present in a synergistically effective amount; 
       in an amount of from 1 to 1000 g/100 kg of seed. 
     
     
         23 . The seed of  claim 22 , wherein the azolopyrimidinylamine of formula I is of the formula IA 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is C 3 -C 12 -alkyl, C 5 -C 12 -alkoxyalkyl, phenyl or phenyl-C 1 -C 4 -alkyl, where phenyl may be substituted by one to three groups R b ; 
 R 2  is C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
 R 3  is hydrogen or NH 2 . 
 
     
     
         24 . The seed of  claim 22 , wherein the azolopyrimidinylamine of formula I is selected from the group consisting of
 6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;   6-octyl-5-trifluormethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine and   5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine.   
     
     
         25 . The seed of  claim 22 , wherein the at least one active compound II is selected from the group A, C or E. 
     
     
         26 . The seed of  claim 22 , wherein the at least one active compound II is selected from the group B, D or F. 
     
     
         27 . The seed of  claim 22 , wherein the mixture comprises the azolopyrimidinylamine of formula I and two active compounds II, wherein each active compound II is independently selected from the group A, B, C, D, E or F. 
     
     
         28 . A process for preparing a composition comprising 
       contacting liquid or solid carriers with a mixture of
 1) an azolopyrimidinylamine of formula I 
 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is C 3 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 5 -C 12 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-C 1 -C 4 -alkyl; 
         R 2  is C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
 where the aliphatic chains in R 1  and/or R 2  may be substituted by one to four identical or different groups R a : 
 R a  is halogen, cyano, hydroxyl, mercapto, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or NR A R B ;
 R A , R B  are hydrogen and C 1 -C 6 -alkyl; 
 
 where the cyclic groups in R 1  and/or R a  may be substituted by one to four groups R b : 
 R b  is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , C 1 -C 10 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy; 
 
         R 3  is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkoxy, C 3 -C 8 -cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C 1 -C 6 -alkyl-S(O) m —;
 m is 0, 1 or 2; 
 
         A is CR 3  or N; 
       
       and
 2) at least one active compound II selected from the group consisting of: 
 A) bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole, hymexazole; 
 B) azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate; 
 C) carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide, dimethomorph, flumorph; flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid; N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethanesulfonylamino-3-methylbutyramide; 
 D) fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil triforine, fenpiclonil, fludioxonil aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, amisulbrom, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-5-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; 
 E) mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, and methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propanoate; 
 
       and
 F) dodine, iminoctadine, guazatine; 
 kasugamycin, streptomycin, polyoxine, validamycin A; 
 binapacryl, dinocap, dinobuton; 
 dithianon, isoprothiolane; 
 fentin salts; 
 edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; 
 chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid; 
 Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine; 
 prohexadione and its salts, trinexapac-ethyl, chlormequat, mepiquat-chloride, diflufenzopyr; 
 wherein the azolopyrimidinylamine of formula I and the at least one active compound II of the mixture are present in a synergistically effective amount; 
 
       wherein a composition is prepared.