Gulf Research & Development Company

Gulf Oil Corporation

William C Doyle, Jr

Joel L Kirkpatrick

Loren W Hedrich

Marion F Botts

New fluorosulfonyltriazole compounds which are useful as miticides and inseciticides have the general structural formula ##STR1## and tautomeric forms thereof, in which R is hydrogen, C.sub.1 to C.sub.7 alkyl, alkoxyalkyl, phenoxyalkyl, benzyl, phenyl or C.sub.3 to C.sub.6 cycloalkyl.

5-Substituted-3-fluorosulfonyl-4H-1,2,4-triazoles and use as

Undesired vegetation, including crabgrass, Johnson grass and pigweed are effectively controlled in cotton, corn and peanuts in the warm temperate zones by application of an effective amount of 1,3-dimethyl-1-(5-tert.butyl-1,3,4-thiadiazol-2-yl)urea or the corresponding 1-ethyl-3-methyl compound to the locus of the weeds. A particularly desirable procedure is the use of one of the new herbicides in combination with alachlor to give very broad spectrum weed control, including such noxious weeds as nutsedge.

Combating unwanted vegetation with 1,3,4-thiadiazolylureas

Barban (4-chloro-2-butynyl m-chlorocarbanilate) is formulated as liquid emulsifiable concentrates containing as much as twenty to thirty percent of the herbicide which have improved efficacy and unlike other formulations of higher concentration, are also safe to use in wheat fields. A particularly critical component of the improved concentrate is a condensation product of C.sub.12 to C.sub.18 fatty alcohols with from ten to forty units of ethylene oxide.

Barban formulation

Triazolylsulfonamides of a limited class are substantially non-phytotoxic and are useful as insecticides. For example 1-N,N-dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N,N-dimethylsulfona mide is effective in aphid control, both by foliar application and systemically.

1-Dimethylcarbamyl-3-branched alkyl-1,2,4-triazol-5-yl-(N-substituted)

A class of 5-ureido and thioureido-1,3,4-thiadiazole-2-sulfonamides bearing various substituents on both sulfonamide and ureido nitrogen atoms is employed to combat unwanted vegetation both pre- and post-emergently.

Combating unwanted vegetation with 1,3,4-thiadiazole-2-sulfonamides

Unwanted vegetation is combated in the presence of grain crops and soybeans by post-emergent application of one or more of the following compounds:

Selectively herbicidal 2-substituted-4H-3,1-benzoxazin-4-ones

The industrial herbicide 5-(1,3,3-trimethylureido)-N,N-dimethyl-1,3,4-thiadiazole-2-sulfonamide and other compounds of similar structure may be made by a novel procedure in which the first step is the oxidative chlorination of a 2-alkylamino-5-mercapto-1,3,4-thiadiazole to yield the corresponding sulfonyl chloride. The subject compound which possesses five methyl substituent groups is more effective as a herbicide than compounds which contain other alkyl substituents or a lesser number of methyl substituents.

Growing community of inventors

Leawood, KS, United States of America

William C Doyle, Jr