Chevron Research Company

Chevron Research

Stephen D Ziman

David C Chan

Richard N Reynolds, Jr

Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are alkyl or halo; R.sup.3 is hydrogen or alkyl; Z is halo; and R.sup.4 is alkoxycarbonyl, alkoxy, phenyl, substituted phenyl,

Herbicidal and plant-growth-regulating

Compounds of the formula ##STR1## wherein R.sup.1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 5 of the same or different substituents selected from fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; X is fluoro, bromo, chloro, iodo or alkoxy of 1 to 3 carbon atoms; W and Z are hetero atoms in an aromatic 5-membered ring independently selected from the group consisting of nitrogen, sulfur and oxygen; and n=0, 1 or 2, have herbicidal and plant growth regulating activity.

Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilide

1,2,4-Trisubstituted-1,2,4-triazolidin-3,5-dithiones are prepared by the reaction of a 1,2,4-trisubstituted 1,2,4-triazolidin-3-one-5-thione and phosphorous pentasulfide in the liquid phase. The triazolidin-dithione compounds are useful as herbicides and plant-growth regulators.

A novel process for making 3-(N-arylamino)-gamma-butyrothiolactones from their corresponding butyrolactone analogs is disclosed. The thiolactone products are useful intermediates for making fungicidal compounds.

Process for making 3-(N-arylamino)-gamma-butyrothiolactones

1,2,4-Trisubstituted-1,2,4-triazolidin-3-one-5-thiones are prepared by the reaction of a 1,4-disubstituted 1,2,4-triazolidin-3-one-5-thione and an organohalide in the liquid phase in the presence of a base. The triazolidinonethione compounds are useful as herbicides and plant-growth regulators.

Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl groups containing 1 to 6 carbon atoms; R.sup.3 is a haloalkyl group of the formula C.sub.m Y.sub.(m-1) X.sub.(m+2) wherein X is fluoro, chloro, bromo or iodo and m=1 or 2; Y is hydrogen, fluoro, chloro, bromo or iodo; R.sup.4 is hydrogen, an alkyl group containing 1 to 6 carbon atoms, alkoxy containing 1 to 6 carbon atoms, alkenyl containing 2 to 6 carbon atoms, nitro, hydroxy, alkoxyalkyl containing 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo and n-1, 2, 3 or 4, have fungicidal activity.

Fungicidal n-substituted 4,4-dialkyl homophthalimides

A process for making a compound of the formula ##STR1## which process comprises contacting, in the absence of an acid acceptor, an acyl halide with an aniline substituted gamma-butyrolactone in the presence of a non-basic solvent and at a temperature between 65.degree. and 150.degree. C. Thus, 3-(N-chloroacetyl-N-2,6-dimethylphenylamino)-gamma-butyrolactone is prepared by a process comprising contacting, in the absence of an added acid acceptor, chloroacetylchloride with 3-(N-2,6-dimethylphenylamino)-gamma-butyrolactone in the presence of a non-basic organic solvent and at a temperature between 65.degree. and 150.degree. C. Preferably, the 3-(N-2,6-dimethylphenylamino)-gamma-butyrolactone is formed by reacting alpha-bromo-gamma-butyrolactone with dimethylaniline in the presence of water and in a non-basic organic solvent, and the 3-(N-2,6-dimethylphenylamino)-gamma-butyrolactone in the organic solvent is phase separated and fed straight through to the acetylation step.

Acylation of a lactone-substituted aniline compound in the absence of an

Novel 2,3,5-trisubstituted-1,2,3,5-thiatriazolidin-4-one-2-oxides have been found to have herbicidal activity. These 1,2,3,5-thiatriazolidin-4-one-2-oxides are prepared by reacting an N-aminourea (semicarbazide) and thionyl chloride.

Growing community of inventors

San Francisco, CA, United States of America

Stephen D Ziman