Monsanto Company

Michael K Mao

Wendell Gary Phillips

Bruce C Hamper

Thomas L Fevig

Chun Ma

The fungicidal compound 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide (Formula (I)) has shown superior and unexpected control of the growth of the soil-borne fungus,(,). The present invention provides a novel compound for synthesizing the compound of Formula (I) which uses the compound 4-hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide (Formula (II)) as well as novel compounds of synthesizing the allylamide. In addition, Formula (II) itself has unexpectedly been found to provide control of,. Therefore, the compounds having Formula (III):

Fungicidal compositions and methods of making thereof

The fungicidal compound 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide (Formula (I) shown superior and unexpected control of the growth of the soil-borne fungus Gaeumannomyces graminis (Gg). The present invention provides a novel compound for synthesizing the compound of Formula (I) which uses the compound 4-hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide (Formula (II)) as well as novel compounds of synthesizing the allylamide. In addition, Formula (II) itself has unexpectedly been found to provide control of Gg. Therefore, the compounds having Formula (III): ##STR1## or an agronomic salts and compositions thereof are expected to provide such control as well; wherein:

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-[1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1H-pyrazole-3-yl]-2,4-dihalo-benzoic acids such as isopropyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl]-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-[1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1H-pyrazole-3-yl]-2,4-dihalo-benzoic acids such as isopropyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl]-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyldiketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-[1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1 H-pyrazole-3-yl]-2,4-dihalo-benzoic acids such as isopropyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-1 H-pyrazole-3-yl]-2-chloro-4-fluorobenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5- �1-(C.sub.1-5 alkyl) -4-halo-5-(C.sub.1-3 haloalkyl) -1H-pyrazole-3-yl!-2,4-dihalo-benzoic acids such as isopropyl 5-�4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl!-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

Esterification of benzoic acid substituents of

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-�1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1H-pyrazole-3-yl!-2,4-dihalo-benzoic acids such as isopropyl 5-�4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl!-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-�1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1H-pyrazole-3-yl!-2,4-dihalo-benzoic acids such as isopropyl 5-�4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl!-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyldiketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

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Chesterfield, MO, United States of America

Michael K Mao