Uniroyal Inc.

Robert W Neidermyer

Walter Gerhard Brouwer

Ethel Ellen Felauer

Ronald B Ames

Bruce A Graham

Michael A Puttock

Edwin J MacPherson

Arthur D Brewer

William S McIntire

Charles E Crittendon

Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre- and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.

Substituted dithiin tetroxide plant growth regulants

Substituted 2,3-dihydro-1,4-oxathiins of the formula ##STR1## display useful plant growth regulant effects including herbicidal effects. Examples are 2,3-dihydro-5,6-diphenyl-1,4-oxathiin, and 2,3-dihydro-5-(4-methylphenyl)-6-phenyl-1,4-oxathiin 4-oxide. The compounds are useful for the selective control of grasses and as dwarfing agents, as well as for inhibition of vegetative and reproductive axillary growth, and for increasing the sugar content of sugar producing species. A number of these are new compounds.

Substituted 2,3-dihydro-1,4-oxathiin plant growth regulants

Plant growth regulant effects, such as dwarfing, cessation of terminal growth, increased flower set, increased fruit and pod set, fruiting body abortion, twisting and epinastic responses, etc., may be accomplished on crops such as soybeans, cotton, etc., by application of certain 2-(1,3,4-oxadiazol-2-yl) or 2-(2-oxazolyl) or 2-(1,3,4-thiadiazol-2-yl)benzoic acids, salts and esters, having the formula ##STR1## where X is nitrogen or C-R' (R' being hydrogen or methyl), Z is oxygen or sulfur when X is nitrogen, Z is oxygen when X is C-R', R is phenyl or various substituents, and R' is hydrogen or various substituents. An example is 2-(5-phenyl-1,3,4-oxadiazol-2-yl) benzoic acid. The compounds where X is nitrogen and Z is sulfur are new compounds, e.g., 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid.

2-(5-Phenyl-1,3,4-thiadiazol-2-yl)benzoic acid

Plant growth regulation using certain substituted

Plant growth regulant effects, such as dwarfing, cessation of terminal growth, increased flower set, increased fruit and pod set, fruiting body abortion, twisting and epinastic responses, etc., may be accomplished on crops such as soybeans, cotton, etc., by application of certain 2-(1,3,4-oxadiazol-2-yl) or 2-(2-oxazolyl) or 2-(1,3,4-thiadiazol-2-yl)benzoic acids, salts and esters, having the formula ##STR1## where X is nitrogen or C--R' (R' being hydrogen or methyl), Z is oxygen or sulfur when X is nitrogen, Z is oxygen and when X is C--R', R is phenyl or various substituents, and R' is hydrogen or various substituents. An example is 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid. The compounds where X is nitrogen and Z is sulfur are new compounds, e.g., 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid.

Method of retarding the growth of plants using certain oxadiazolyl,

Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre-and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.

Substituted 2,3-dihydro-1,4-oxathiin plant growth

Herbicidal method employing substituted dithin tetroxides

New 2-(1,3,4-oxadiazole-2-yl) benzoic acids and salts and esters thereof, as well as certain 2-(2-oxazolyl) benzoic acids, salts and esters, having the formula: ##SPC1## Where X is nitrogen or C-R' (R' being hydrogen or methyl), R is phenyl or various substituents, and R' and the Y's are hydrogen or various substituents, are effective preemergence or postemergence herbicides, on various crops. The chemicals act selectively and are useful against purple nutsedge and in cranberry. Oxadiazoles of the invention may be made by reacting a benzhydrazide with phthalic anhydride to form a hydrazide which is cyclized by removal of the elements of water, using as a catalyst fuming sulfuric acid or dimethylformamide-sulfur trioxide complex.

Oxadiazole benzoic acid derivatives as herbicides

Plant growth regulant effects, such as dwarfing, cessation of terminal growth, increased flower set, increased fruit and pod set, fruiting body abortion, twisting and epinastic responses, etc., may be accomplished on crops such as soybeans, cotton, etc., by application of certain 2-(1,3,4-oxadiazol-2-yl) or 2-(2-oxazolyl) or 2-(1,3,4-thiadiazol-2-yl)benzoic acids, salts and esters, having the formula ##SPC1## Where X is nitrogen or C--R' (R' being hydrogen or methyl), Z is oxygen or sulfur when X is nitrogen, Z is oxygen when X is C--R', R is phenyl or various substituents, and R' is hydrogen or various substituents. An example is 2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoic acid. The compounds where X is nitrogen and Z is sulfur are new compounds, e.g., 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid.

Plant growth regulants

Substituted 2,3-dihydro-1,4-oxathiins of the formula ##SPC1## Display useful plant growth regulant effects including herbicidal effects. Examples are 2,3-dihydro-5,6-diphenyl-1,4-oxathiin, and 2,3-dihydro-5-(4-methyl-phenyl)-6-phenyl-1,4-oxathiin 4-oxide. The compounds are useful for the selective control of grasses and as dwarfing agents, as well as for inhibition of vegetative and reproductive axillary growth, and for increasing the sugar content of sugar producing species. A number of these are new compounds.

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Cheshire, CT, United States of America

Robert W Neidermyer