The Dow Chemical Company

Dowelanco

Merrell Dow Pharmaceuticals

Walter Reifschneider

Mark J Costales

William A Kleschick

Robert J Ehr

Kim Eric Arndt

John C Van Heertum

Barat Bisabri-Ershadi

James E Dripps

J Brian Barron

Doris L Paroonagian

John J Jachetta

Donald H DeVries

Larry L Larson

Kimberly Brubaker Bradley

Timothy Calvin Johnson

Zoltan Laszlo Benko

Mary L Ash

Beth A Swisher

Donald H De Vries

Doris L Parconagian

Zolt An Benk O

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-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

O,S-Dailkyl ((nitrogen heterocyclyl)carbonyl)phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with selected five and six membered nitrogen heterocycles and found to be effective plant systemic and contact insecticides. Ethyl 1-(((methoxy(methylthio)phosphinyl)amino)carbonyl)-4-piperidinecarboxylate , for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and ethyl 4-piperidinecarboxylate and found to control aster leafhopper when applied to rice plants.

((N-heterocyclyl)carbonyl)phosphoramidothioate ester insecticides

O,S-Dialkyl ((nitrogen heterocyclyl)carbonyl)-phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with selected 5 and 6 membered nitrogen heterocycles, such as thiomorpholine and tetrahydroquinoline, and found to be effective plant systemic and contact insecticides. O,S-dimethyl ((4-thiomorpholinyl)carbonyl)phosphoramidothioate, for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and thiomorpholine and found to control aster leafhopper when applied to rice plants.

Ester and amide derivatives of N-(((alkoxy-(alkylthio)phosphinyl)amino)carbonyl)amino)alkanecarboxylic acids of the formula: ##STR1## (wherein R.sup.2 represents an alkyl group containing a carboxylic acid ester or amide moiety) were prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates and ester and amide derivatives of naturally occurring and synthetic aminoacids and were found to be effective plant systemic and contact insecticides. Ethyl N-(((methoxy(methylthio)phosphinyl)amino)-carbonyl)methioninate, for example, were prepared from O,S-dimethyl phosphoroisocyanatidothioate and ethyl methioninate and found to control aster leafhoppers when applied to rice plants.

N-(((alkoxy(alkylthio)phosphinyl)amino)carbonyl)-aminoalkanoate ester

O,S-Dialkyl ((piperazinyl)carbonyl)phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with substituted piperazines and found to be effective plant systemic and contact insecticides. ((4-(1,1-Dimethylethyl)-1-piperazinyl)carbonyl)phosphoramidothioate, for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and 4-(1,1-dimethylethyl)piperazine and found to control aster leafhoppers when applied to rice plants.

((1-piperazinyl)carbonyl)phosphoramidothioate ester insecticides

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

The compound, 2-chloro-4-((cyanomethyl)thiolphenyl N-methyl carbamate, is a therapeutic agent in the treatment of patients afflicted with carcinomas or lymphocytic leukemia.

2-chloro-4-((cyanomethyl)thio)phenyl N-methyl carbamate for treating

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.

Compounds of the formula: ##STR1## wherein R is hydrogen; alkyl of 1 to 8 carbons; alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl wherein alkyl contains 1 to 4 carbons; phenyl; phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons;

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Walnut Creek, CA, United States of America

Walter Reifschneider