The Dow Chemical Company

Dowelanco

Dow Agrosciences LLC

Other

William A Kleschick

Robert J Ehr

Norman R Pearson

Mark J Costales

John C Van Heertum

Ben C Gerwick, Iii

Anna P Vinogradoff

William T Monte

Walter Reifschneider

Timothy Calvin Johnson

Kim Eric Arndt

Chrislyn M Carson

Richard Kevin Mann

Joseph E Dunbar

Mark Andrew Pobanz

John J Jachetta

Richard W Meikle

Timothy P Martin

Richard Duane Johnston

Richard W Meikle, Deceased

Kimberly Brubaker Bradley

Shannon L Bartley

Zoltan Laszlo Benko

Monte Ray Weimer

Theodore W Holmsen

Patricia G Ray

Mary L Ash

Beth A Swisher

Ben Clifford Gerwick, Iii

Jacob Secor

Pearson, Norman R

By Diane Meikle, Executrix

Deceased Meikle

Zolt An Benk O

N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]-triazolo[1,5-c]pyrimidin-2-yl)b enzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]-triazolo[1,5-c]pyrim idin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo-[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]-pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

N-([1,2,4]triazoloazinyl)benzenesulfonamide and pyridinesulfonamide

N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)be nzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimi din-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy�1,2,4!-triazolo�1,5-c!pyrimidin-2-yl)b enzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy�1,2,4!-triazolo�1,5-c!pyrim idin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy�1,2,4!triazolo�1,5-a!pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino�1,2,4!triazolo-�1,5-c!pyrimidine and 2-amino�1,2,4!triazolo�1,5-a!-pyridine compounds and appropriately substituted benzene-sulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

N-(�1, 2, 4! triazoloazinyl) benzenesulfonamide and pyridinesulfonamide

Substituted N-(1-ethyl-4-pyrazolyl)triazoloazinesulfonamide compounds, such as N-(1-ethyl-5-methyl-3-(trifluoromethyl)-4-pyrazoyl)-5-methoxy-7-methyl-�1, 2,4!triazolo�1,5-c!pyrimidine-2-sulfonamide and N-(1-ethyl-5-methyl-3-(trifluoromethyl)-4-pyrazolyl)-5-methoxy-7-methyl�1, 2,4!triazolo�1,5-a!pyridine-2-sulfonamide, were prepared and found to possess selective herbicidal utility. The compounds are especially useful for the preemergence control of grassy weeds in soybeans

N-(1-ethyl-4-pyrazolyl)triazoloazinesulfonamide herbicides

Substituted N-aryl�1,2,4!triazolo�1,5-a!pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl�1,2,4!triazolo�1,5-a!pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazolyl)-8-chloro-5-methoxy�1,2,4!triazolo�1,5-a!p yridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro�1,2,4!triazolo�1,5-a!p yridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl�1,2,4!triazolo�1,5-a!pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.

N-aryl�1,2,4!triazolo�1,5-a!pyridine-2-sulfonamide herbicides

Substituted N-pyridinyl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compounds, such as N-(2-fluoro-4-methyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide, were prepared bycondensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminopyridine compound, such as 3-amino-2-fluoro-4-methylpyridine, and found to possess herbicidal utility.

N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides

Substituted N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide compounds, such as N-(2,6-difluorophenyl)-5-methoxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2- sulfonamide, N-(4-bromo-1-methyl-3-pyrazoly)-8-chloro-5-methoxy[1,2,4]triazolo[1,5-a]py ridine-2-sulfonamide, and N-(2-fluoro-4-methyl-3-pyridinyl)-8-ethoxy-6-chloro[1,2,4]triazolo[1,5-a]- pyridine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyridine compound with an aryl amine. The compounds prepared were found to possess excellent herbicidal activity on a broad spectrum of vegetation at low application rates.

N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides

Substituted N-pyridinyl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compounds, such as N-(2-fluoro-4-methyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminopyridine compound, such as 3-amino-2-fluoro-4-methylpyridine, and found to possess herbicidal utility.

Substituted N-indazolyl[1,2,4]triazolo[1,5]-c-pyrimidine-2-sulfonamide compounds, such as N-(4-fluoro-1-methyl-3-indazolyl)-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]p yrimidine-2-sulfonamide, were prepared by condensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminoindazole compound, such as 3-amino-4-fluoro-1-methylindazole, and found to possess herbicidal utility.

N-indazolyl[1,2,4]triazolo[1,5-C]pyrimidine-2-sulfonamide herbicides

N-(3-, 4-, and 5-)-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide compounds, substituted on the pyrimidine ring with an alkoxy group and on the pyrazine ring, such as N-(4-bromo-1-methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]p yrimidine-2-sulfonamide, were prepared from alkoxy substituted 1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonyl halides by condensation with substituted (3-, 4-, and 5-aminopyrazoles in the presence of a pyridine base and a catalytic amount of dimethyl sulfoxide. The compounds were found to possess general and, in some cases, selective pre- and postemergence herbicidal activity.

N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides

5-Alkoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamides are prepared from 5-alkoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl halides by condensation with ortho-substituted N-trialkylsilylanilines and by other methods. N-(2,6-dichloro-3-methylphenyl)-8-fluoro-5-methoxy-1,2,4-triazolo[1,5-c]py rimidine-2-sulfonamide is typical. The compounds are general and selective pre- and postemergence herbicides.

Herbicidal alkoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamides

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

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

Alkoxy substituted 1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonamides are prepared from alkoxy substituted 1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl halides by condensation with substituted N-trialkylsilylanilines and by other methods. N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo[1,5-c]pyrimid ine-2-sulfonamide is typical. The compounds are general and selective pre- and postemergence herbicides.

Herbicidal alkoxy-1,2,4-triazolo(1,5-c)primidine-2-sulfonamides

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.

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Indianapolis, IN, United States of America

William A Kleschick