Microbiocidal 2-acylamino-thiazole-4-carboxamide derivatives

1 . A compound of formula (I):

wherein,

Y is C;

R 1 is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 hydroxyalkyl, methoxyC 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 2 alkoxyC 1 -C 2 alkoxy, C 1 -C 3 alkoxycarbonyl, methoxycarbonylC 1 -C 3 alkyl, C 1 -C 2 alkoxycarbonyloxyC 1 -C 2 alkyl, C 1 -C 2 alkycarbonyloxyC 1 -C 2 alkyl, C 3 -C 4 alkynyloxy, C 1 -C 3 alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC 1 -C 2 alkyl, or heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising a single heteroatom selected from oxygen and sulfur;

R 2 is C 1 -C 4 alkyl

R 3 is C 3 -C 4 cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R 4 , or R 3 is a 6- to 8-membered non-aromatic spirocyclic carbobi-cyclyl ring system;

R 4 is C 1 -C 4 alkyl;

X is N;

or a salt or an N-oxide thereof.

2 . The compound according to claim 1 , wherein R 1 is hydrogen, methyl, ethyl, methoxy, ethoxy, fluoromethyl, chloromethyl, bromomethyl, 2,2,2-trifuoroethyl, 1-hydroxyethyl, methoxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1-methoxy-1-methylethyl, cyclopropyl, methoxyethoxy, ethoxycarbonyl, 2-methoxy-2-oxo-ethyl, 2-methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1-ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxymethyl, 1-benzyloxyethyl, 2-furanyl, or 2-thiophenyl.

3 . The compound according to claim 1 , wherein R 2 is methyl.

4 . The compound according to claim 1 , wherein R 3 is cyclobutyl, 2,2-dimethylcyclobutyl or spiro[3.4]octanyl.

5 . The compound according to claim 1 , wherein R 1 is hydrogen, methyl, ethyl, methoxy, ethoxy, fluoromethyl, 2,2,2-trifuoroethyl, cyclopropyl, methoxyethoxy, 2-methoxy-2-oxo-ethyl, 2-methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, isopropylsulfanyl, phenyl, phenoxy, 2-furanyl, or 2-thiophenyl.

6 . An agrochemical composition comprising a fungicidally effective amount of the compound of formula (I) according to claim 1 .

7 . The composition according to claim 6 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

8 . A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, applying a fungicidally effective amount of the compound of formula (I) according to claim 1 to the plants, to parts thereof or the locus thereof.

9 . A compound selected from:

[2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2-oxo-ethyl] acetate;

[2-[[4-(cyclobutylcarbamoyl)-5-methyl-thiazol-2-yl]-(2,6-difluoro-4-pyridyl)amino]-1-methyl-2-oxo-ethyl] ethyl carbonate;

[2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2-oxo-ethyl] methyl carbonate;

[2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2-oxo-ethyl] ethyl carbonate;

2-[(2,6-difluoro-4-pyridyl)-(2-hydroxypropanoyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide;

2-[2-benzyloxypropanoyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide;

N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4-carboxamide;

[2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2-oxo-ethyl] acetate;

2-[(2,6-difluoro-4-pyridyl)-(2-phenylacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methoxy-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide;

2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide;

N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4-carboxamide;

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide;

2-[(2-benzyloxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-[(2,6-difluoro-4-pyridyl)-(2-ethoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-[diethylcarbamoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-3-oxo-propanoate;

2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

methyl 5-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-5-oxo-pentanoate;

2-[(2,6-difluoro-4-pyridyl)-(3,3,3-trifluoropropanoyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

S-isopropyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamothioate;

methyl 4-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-4-oxo-butanoate;

2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

prop-2-ynyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamate;

phenyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamate;

2-[(2,6-difluoro-4-pyridyl)-(2-fluoroacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-methoxyethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamate;

2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

ethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamate;

2-[(2,6-difluoro-4-pyridyl)-(thiophene-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

methyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]carbamate;

2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide;

ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2-oxo-acetate;

2-[benzoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide;

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide; or

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide.

10 . The compound of claim 9 , wherein the compound is selected from:

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methoxy-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide;

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide;

methyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]arbamate;

ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2-oxo-acetate;

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide; or

2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide.

11 . An agrochemical composition comprising a fungicidally effective amount of the compound according to claim 9 .

12 . The composition according to claim 11 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.