The Dow Chemical Company

Merrell Dow Pharmaceuticals

Anna P Vinogradoff

William A Kleschick

Joseph E Dunbar

Norton P Peet

Shyam Sunder

Novel substituted pyrazolo[1,5-a]pyrimidine-2-sulfonamide compounds, such as 3-cyano-5,7-dimethyl-N-2,6-dichlorophenylpyrazolo[1,5-a]pyrimidine-2-su lfonamide, were prepared by the condensation of novel substituted 2-benzylthiopyrazolo[1,5-a]pyrimidine compounds, such as 2-benzylthio-5,7-dimethylpyrazolo[1,5-a]pyrimidine, and substituted anilines and found to be useful as herbicides.

Pyrazolo[1,5-a]pyrimidine-2-sulfide compounds

Novel compounds, e.g. 3-cyano-5,7-dimethyl-N-(2,6-dichlorophenyl)pyrazolo[1,5-a]pyrimidine-2-sul fonamide and their use as herbicides and/or for the suppression of nitrification of ammonium nitrogen in soil.

Pyrazolo[1,5-a]pyrimidine-2-sulfonyl chloride and -2-sulfide compounds

Novel compounds, e.g. 3-cyano-5,7-dimethyl-N-(2,6-dichlorophenyl)pyrazolo]1,5-a]pyrimidine-2-sul fonamide and their use as herbicides and/or for the suppression of nitrification of ammonium nitrogen in soil.

Substituted pyrazolo[1,5-a]pyrimidine-2-sulfonamides and compositions

Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]pyrimidines are prepared by reacting a desired sulfonamide with dimethyl N-cyanodithioiminocarbonate in the presence of a base followed by reaction with an excess of hydrazine and then a 1,3-dicarbonyl compound. The resulting products have a variety of herbicidal uses.

Process for the preparation of intermediates useful for making

3-(1H-Tetrazol-5-yl)thieno[2,3-d]pyrimidin-4(3H)-ones useful as antiallergic agents are described herein. The compounds are prepared by cyclization of an appropriate substituted amidine using an alkali metal base. The reaction is carried out in an appropriate inert solvent.

3-(1H-tetrazol-5-yl)thieno[2,3-d]pyrimidin-4(3H)-ones

Process for the preparation of herbicidal sulfonamides

A new process for the preparation of 3-(1H-tetrazol-5-yl)-4(3H)-quinazolinones from anthranilic acid derivatives is described herein. Additional reactants used in the process are 4-aminotetrazole and a trialkoxymethane or the reaction can be carried out using the imidic ester obtained from these two compounds.

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Concord, CA, United States of America

Anna P Vinogradoff