Monsanto Company

Monsanto Technology LLC

Rohm and Haas Company

John Kennedy Pratt

Wendell Gary Phillips

Gabriel Hanna. Srouji

Gerhard Horst Alt

Matthew James Graneto

Dennis Paul Phillion

Sai Chi Wong

Karey Alan Van Sant

Daniel Mark Walker

Diane Susan Braccolino

Michael K Mao

Bruce C Hamper

Thomas L Fevig

Chun Ma

Patrick H Lau

Kenneth Wayne Ratts

Van R Gaertner

Gabriel Hanna Srouji

Diane Susan Gerberich

Fungicides for the control of take-all disease of plants

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

A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula

A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, and isothiazole;

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

Fungicides having thiophene rings may be made from the intermediate compound 3-carbomethoxy-4,5-dimethylthiophene. That compound, and related compounds, may be produced by reacting an alpha mercaptoketone, e.g., 3-mercapto-2-butanone, with an acrylate, e.g., methyl-3-methoxy acrylate, in the presence of an alkoxide base, e.g., NaOMe, to form the substituted tetrahydrothiophene, followed by conversion to the aromatic thiophene with an acid treatment. The substituted tetrahydrothiophene is a novel compound.

Synthesis of 3-carbomethoxy-4,5-dimethylthiophene

A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are C and are part of an aromatic ring that is furan;

A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are C or N and are part of an aromatic ring that is thiophene;

Fungicides for the control of Take-All disease of plants

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.

Growing community of inventors

Glencoe, MO, United States of America

Wendell Gary Phillips