The Dow Chemical Company

Dowelanco

Dow Agrosciences LLC

Other

John C Van Heertum

William A Kleschick

Robert J Ehr

Timothy Calvin Johnson

Richard Kevin Mann

Walter Reifschneider

Sudarshan K Malhotra

Mark J Costales

Mark Andrew Pobanz

Timothy P Martin

Kim Eric Arndt

John J Jachetta

Thomas L Siddall

David George Ouse

Zoltan Laszlo Benko

Maria P Herrero

Richard Duane Johnston

Thomas D Thibault

James A Turner

Johnny L Jackson

Gail M Garvin

Jeffrey M McQuiston

Kimberly Brubaker Bradley

Ben C Gerwick, Iii

Patricia G Ray

Mary L Ash

Beth A Swisher

Ben Clifford Gerwick, Iii

Zolt An Benk O

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

N-&lsqb;1,2,4&rsqb;triazoloazinyl) benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides

1-Alkyl-4-benzoyl-5-hydroxypyrazole compounds in which the benzoyl moiety is substituted in the 2-position with a halo, alkyl, or alkoxy group, in the 4-position with an alkylsulfonyl group, and in the 3-position with an optionally substituted phenyl group, for example, 1-(1,1-dimethylethyl)-4-(2-methyl-4-methyl-sulfonyl-3-(4-methoxyphenyl)benzoyl-5-hydroxypyrazole, were prepared and found to be useful for the control of a variety of broadleaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation selectively in small grain crops and turf or non-selectively.

Benzoic acid compounds and their use 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)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-([1,2,4]triazoloazinyl) benzenesulfonamide and pyridinesulfonamide

1-Alkyl-4-benzoyl-5-hydroxypyrazole compounds in which the benzoyl moiety is substituted in the 2-position with a halo, alkyl, or alkoxy group, in the 4-position with an alkylsulfonyl group, and in the 3-position with an optionally substituted phenyl group, for example, 1-(1,1-dimethylethyl)-4-(2-methyl-4-methylsulfonyl-3-(4-methoxyphenyl)benz oyl-5-hydroxypyrazole, were prepared and found to be useful for the control of a variety of broadleaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation selectively in small grain crops and turf or non-selectively.

1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use 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 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)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-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 ring annulated 5-alkoxy-N-aryl-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds, such as N-(2,6-dichlorophenyl)-5-methoxycyclopenteno[d]-[1,2,4]triazolo[1,5-c]pyri midine-2-sulfonamide, were prepared by condensation of an appropriate 2-chloro-sulfonyl-5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-5-methoxycyclopenteno[d][1,2,4]triazolo[1,5-c]pyrimidine, with a substituted arylamine compound, such as 2,6-dichloroaniline, and found to possess herbicidal utility.

Ring annulated

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

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.

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Indianapolis, IN, United States of America

John C Van Heertum