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US 12,696,899 B2Granted
Microbiocidal 2-acylamino-thiazole-4-carboxamide derivatives
AssigneeSyngenta Crop Protection AG
InventorsDavid Burns, Mattia Riccardo Monaco, Stefano Rendine, Clemens Lamberth, Mathias Blum
Life of this patent
Estimating the term…
Abstract
Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, and especially fungicides.
Claims12
A compound of formula (I):
- wherein,
- Y is C;
- R1 is hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3hydroxyalkyl, methoxyC1-C4alkyl, C3-C4cycloalkyl, C1-C2alkoxyC1-C2alkoxy, C1-C3alkoxycarbonyl, methoxycarbonylC1-C3alkyl, C1-C2alkoxycarbonyloxyC1-C2alkyl, C1-C2alkycarbonyloxyC1-C2alkyl, C3-C4alkynyloxy, C1-C3alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC1-C2alkyl, or heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising a single heteroatom selected from oxygen and sulfur;
- R2 is C1-C4alkyl
- R3 is C3-C4cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R4, or R3 is a 6- to 8-membered non-aromatic spirocyclic carbobi-cyclyl ring system;
- R4 is C1-C4alkyl;
- X is N;
- or a salt or an N-oxide thereof.
5 more elements
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.
35 more elements
Dependencies are inferred from the claim text.