The Dow Chemical Company

Dowelanco

Dow Agrosciences LLC

Mark J Costales

Robert J Ehr

William A Kleschick

Walter Reifschneider

Ben C Gerwick, Iii

William T Monte

Norman R Pearson

John C Van Heertum

Kim Eric Arndt

John J Jachetta

Doris L Paroonagian

Richard W Meikle, Deceased

Richard W Meikle

Donald H DeVries

R Garth Pews

Ravi B Shankar

Jack C Little

Kimberly Brubaker Bradley

Timothy Calvin Johnson

Monte Ray Weimer

Patricia G Ray

Mary L Ash

Susan D Thompson

Kidisti G Mariam

Donald H De Vries

Pearson, Norman R

Zolt An Benk O

Deceased Meikle

By Diane Meikle, Executrix

Doris L Parconagian

William A Kleschik

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-aryl[1,2,4]triazolo[1,5-a]-pyrazine-2-sulfonamide compounds, such as 5-bromo-N-(2,6-dichlorophenyl)-8-methoxy[1,2,4]triazolo[1,5-a]-pyrazine-2- sulfonamide, were prepared by condensation of a substituted 2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyrazine compound, such as 5-bromo-2-chlorosulfonyl-8-methoxy[1,2,4]triazolo[1,5-a]pyrazine with a substituted arylamine compound, such as 2,6-dichloroaniline, and found to possess herbicidal utility.

N-aryl[1,2,4]triazolo[1,5-a]pyrazine-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

5-Acylamino-1,2,4-triazole-3-sulfonamides, which are useful intermediates for the preparation of 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide herbicides are prepared from 5-amino-3-mercapto-1,2,4-triazole by sequential acylation to 5-acylamino-3-mercapto-1,2,4-triazoles, chlorination to 5-acylamino-3-chlorosulfonyl-1,2,4-triazoles, and condensation with substituted anilines to 5-acylamino-1,2,4-triazole-3-sulfonamides. 5-Acylamino-3-chlorosulfonyl-1,2,4-triazole compounds are key intermediates in the process.

Preparation of 5-cylamino-1,2,4-triazole-3-sulfonamides

Preparation of 5-acylamino-1,2,4-triazole-3-sulfonamides

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

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

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

The insecticidal activity of certain pyridinyl phosphorus compounds is enhanced by the admixture therewith of certain 2,4-disubstituted-5-pyrimidinyl phosphoramidothioates.

Method and composition for enhancing the insecticidal activity of

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

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.

The insecticidal activity of certain O,O-dialkyl pyridinyl phosphorus ester compounds is enhanced by the admixture therewith of certain substituted pyridinyl phosphoramidates or phosphoramidothioates.

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Concord, CA, United States of America

Mark J Costales