# US 2014/0155263 A1 · Fungicidal Mixtures Based on Azolopyrimidinylamines

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- Number: US 2014/0155263 A1
- Document ID: US20140155263A1
- Status: Published application
- Kind: A1
- Application number: 14/176,554
- Filed: 2014-02-10
- Published: 2014-06-05
- Earliest claimed: 2008-01-24
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Christine Beck; Matthias NIEDENBRÜCK; Maria Scherer; Reinhard Stierl; Siegfried Strathmann; Udo HÜNGER
- Web page: https://patentgrep.com/patent/US20140155263A1

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## 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.

## Claims

### Claim 1

A fungicidal mixture comprising, as active components:
1) an azolopyrimidinylamine of formula I
wherein:
R1 is C3-C12-alkyl, C2-C12-alkenyl, C5-C12-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
R2 is C1-C12-alkyl, C2-C12-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl or NRARB;
RA, RB are hydrogen and C1-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, carboxyl, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C1-C6-alkyl-S(O)m—;
m is 0, 1 or 2;
A is CR3 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

The fungicidal mixture of claim 1, wherein the azolopyrimidinylamine of formula I is of the formula IA
wherein
R1 is C3-C12-alkyl, C5-C12-alkoxyalkyl, phenyl or phenyl-C1-C4-alkyl, where phenyl may be substituted by one to three groups Rb;
R2 is C1-C12-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
R3 is hydrogen or NH2.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

The fungicidal mixture of claim 1, wherein the at least one active compound II is selected from the group A, C or E.

### Claim 6 (depends on 1)

The fungicidal mixture of claim 1, wherein the at least one active compound II is selected from the group B, D or F.

### Claim 7 (depends on 1)

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.

### Claim 8

A composition comprising
a liquid or solid carrier; and
a mixture of
1) an azolopyrimidinylamine of formula I
wherein:
R1 is C3-C12-alkyl, C2-C12-alkenyl, C5-C12-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
R2 is C1-C12-alkyl, C2-C12-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl or NRARB;
RA, RB are hydrogen and C1-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, carboxyl, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C1-C6-alkyl-S(O)m—;
m is 0, 1 or 2;
A is CR3 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.

### Claim 9 (depends on 8)

The composition of claim 8, wherein the azolopyrimidinylamine of formula I is of the formula IA
wherein
R1 is C3-C12-alkyl, C5-C12-alkoxyalkyl, phenyl or phenyl-C1-C4-alkyl, where phenyl may be substituted by one to three groups Rb;
R2 is C1-C12-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
R3 is hydrogen or NH2.

### Claim 10 (depends on 8)

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.

### Claim 11 (depends on 8)

The composition of claim 8, wherein the at least one active compound II is selected from the group A, C or E.

### Claim 12 (depends on 8)

The composition of claim 8, wherein the at least one active compound II is selected from the group B, D or F.

### Claim 13 (depends on 8)

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.

### Claim 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:
R1 is C3-C12-alkyl, C2-C12-alkenyl, C5-C12-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
R2 is C1-C12-alkyl, C2-C12-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl or NRARB;
RA, RB are hydrogen and C1-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, carboxyl, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C1-C6-alkyl-S(O)m—;
m is 0, 1 or 2;
A is CR3 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.

### Claim 15 (depends on 14)

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.

### Claim 16 (depends on 14)

The method of claim 14, wherein the azolopyrimidinylamine of formula I is of the formula IA
wherein
R1 is C3-C12-alkyl, C5-C12-alkoxyalkyl, phenyl or phenyl-C1-C4-alkyl, where phenyl may be substituted by one to three groups Rb;
R2 is C1-C12-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
R3 is hydrogen or NH2.

### Claim 17 (depends on 14)

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.

### Claim 18 (depends on 14)

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.

### Claim 19 (depends on 14)

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.

### Claim 20 (depends on 14)

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.

### Claim 21 (depends on 14)

The method of claim 14, wherein harmful fungi from the class of Oomycetes are controlled.

### Claim 22

Seed, comprising a mixture of
1) an azolopyrimidinylamine of formula I
wherein:
R1 is C3-C12-alkyl, C2-C12-alkenyl, C5-C12-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
R2 is C1-C12-alkyl, C2-C12-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl or NRARB;
RA, RB are hydrogen and C1-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, carboxyl, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C1-C6-alkyl-S(O)m—;
m is 0, 1 or 2;
A is CR3 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.

### Claim 23 (depends on 22)

The seed of claim 22, wherein the azolopyrimidinylamine of formula I is of the formula IA
wherein
R1 is C3-C12-alkyl, C5-C12-alkoxyalkyl, phenyl or phenyl-C1-C4-alkyl, where phenyl may be substituted by one to three groups Rb;
R2 is C1-C12-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
R3 is hydrogen or NH2.

### Claim 24 (depends on 22)

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.

### Claim 25 (depends on 22)

The seed of claim 22, wherein the at least one active compound II is selected from the group A, C or E.

### Claim 26 (depends on 22)

The seed of claim 22, wherein the at least one active compound II is selected from the group B, D or F.

### Claim 27 (depends on 22)

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.

### Claim 28

A process for preparing a composition comprising
contacting liquid or solid carriers with a mixture of
1) an azolopyrimidinylamine of formula I
wherein:
R1 is C3-C12-alkyl, C2-C12-alkenyl, C5-C12-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
R2 is C1-C12-alkyl, C2-C12-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkyl or NRARB;
RA, RB are hydrogen and C1-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, carboxyl, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, or C1-C6-alkyl-S(O)m—;
m is 0, 1 or 2;
A is CR3 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.