The Dow Chemical Company

Dowelanco

Norman R Pearson

William A Kleschick

Robert J Ehr

Mark J Costales

William T Monte

Ben C Gerwick, Iii

Chrislyn M Carson

Richard W Meikle

Richard W Meikle, Deceased

Shannon L Bartley

Andrew S Kende

Jon A Orvik

Timothy J Adaway

Larry D Kershner

Anthony P Haag

William A Kleschik

By Diane Meikle, Executrix

Deceased Meikle

Alkyl 3-chloroanthranilates are the major product from the chlorination of alkyl esters of anthranilic acid with 1,3-dichloro-5,5-dimethylhydantoin. The 3-chloro isomer can be readily separated from the accompanying 5-chloro isomer by selective acetylation of the latter.

Process for the preparation of alkyl 3-chloroanthranilates

N-(Substituted-phenyl)-7-ethoxy-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimid ine-2-sulfonamides are prepared from 2-benzylthio-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines and found to be herbicidal. The compounds, illustrated by 7-ethoxy-5-fluoromethyl-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5-a ]-pyrimidine-2-sulfonamide, are degradable in the soil and are selective to wheat.

7-ethoxy-5-fluoromethyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides

A method for preparing substituted phenoxyphenols which are useful in the preparation of herbicidal (phenoxyphenoxy)propionates is disclosed. The process involves the oxidation of substituted phenoxyphenones to the corresponding phenoxyphenyl esters and their conversion to the desired phenoxyphenol. Novel intermediates for the process are similarly disclosed.

Phenoxyphenoxypropionates, intermediates thereof and methods of

Novel substituted triazolo [1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salts are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.

2,6-disubstituted anilines

N-(Substituted-phenyl)-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sul fonamides are prepared from 2-benzylthio-5-fluoromethyl-1,2,4-triazolo[1,5-a]-pyrimidines and found to be herbicidal. The compounds, illustrated by 5-fluoromethyl-7-methoxy-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5- a]pyrimidine-2-sulfonamide, are degradable in the soil.

5-fluoromethyl-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonamides

N-(Substituted-phenyl)-7-ethoxy-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimid ine-2-sulfonamides are prepared from 2-benzylthio-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines and found to be herbicidal. The compounds, illustrated by 7-ethoxy-5-fluoromethyl-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5-a ]pyrimidine-2-sulfonamide, are degradable in the soil and are selective to wheat.

7-ethoxy-5-fluoromethyl-1,2,4-triazole[1,5-a]-pyrimidine-2-sulfonamindes

Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salt are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.

Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions

N-(Substituted-phenyl)-5-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sul fonamides are prepared from 2-benzylthio-5-fluoromethyl-1,2,4-traizolo[1,5-a]pyrimidines and found to to be herbicidal. The compounds, illustrated by 5-fluoromethyl-7-methoxy-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5- a]pyrimidine-2-sulfonamide, are degradable in the soil.

5-Fluoromethyl-1,2,4-triazolo(1,5-A)-pyrimidines

Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides

Novel substituted imidazolo[1,2-a[pyrimidine-2-sulfonanilides are prepared are prepared from novel substituted imidazolo[1,2-a]pyrimidine-2-sulfonic acids by conversion to the corresponding sulfonyl halides and condensation with substituted anilines and by other methods. N-(2,6-difluorophenyl)-3-chloro-4,6-dimethylimidazolo[1,2-a]pyrimidine-2-s ulfonamide is typical of the compounds prepared. The compounds are useful general and selective pre- and post-emergence herbicides.

Herbicidal imidazolo(1,2-a)pyrimidine-2-sulfonanilides

Novel compounds, e.g., 5,7-dimethyl-N-(2,6-dichlorolphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sul fonamide and their compositions and use in the control of weeds and in the suppression of nitrification of ammonium nitrogen in soil. Other novel compounds and their compositions and use in the inhibition of bolting in sugar beets. Other novel compounds and their compositions and use as plant gametocides.

Novel substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides and

Novel compounds, e.g., 5,7-dimethyl-N-(2,6-dichlorolphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sul fonamide and their compositions and use in the control of weeds and in the suppression of nitrificatin of ammonium nitrogen in soil. Other novel compounds and their compositions and use in the inhibition of bolting in sugar beets. Other novel compounds and their compositions and use as plant gametocides.

Substituted 1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides and

Novel substituted imidazolo[1,2-a]pyrimidine-2-sulfonanilides are prepared from novel substituted imidazolo[1,2-a]pyrimidine-2-sulfonic acids by conversion to the corresponding sulfonyl halides and condensation with substituted anilines and by other methods. N-(2,6-difluorophenyl)-3-chloro-4,6-dimethylimidazolo[1,2-a]pyrimidine-2-s ulfonamide is typical of the compounds prepared. The compounds are useful general and selective pre- and post-emergence herbicides.

Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides

Novel compounds, e.g., N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]-1,3,5-triazin-2-yl)-(2-chlorobenzene sulfonamide) and their compositions and use in the control of weeds.

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Walnut Creek, CA, United States of America

Norman R Pearson