GB978860A - New carbanilic acid esters and their use as herbicides and preparations containing them - Google Patents

Abstract

The invention comprises compounds of formula <FORM:0978860/C1/1> wherein R is a saturated or unsaturated C1- 4 aliphatic hydrocarbon radical optionally halogen-substituted, X and X1 are each O or S. Exemplified are compounds in which (a) X=X1=O and R=i-Pr, (b) X=S, X1=O and R=i-Pr, (c) X=O, X1=S and R=i-Pr, and (d) X=X1=O and R=s-Bu, such compounds being prepared by reaction with the appropriate alcohol of the corresponding isocyanate or isothiocyanate. Other preparative methods mentioned are (1) reaction with the appropriate chloroformic ester of 3-methoxy or 3-methylthioaniline and (2) reaction with the appropriate alcohol of 3-methoxy or 3-methylthio-benzoic acid N-chloramide. Intermediates. 3-methoxyphenyl isocyanate and isothiocyanate are made by reacting 3-methoxyaniline with phosgene or thiophosgene; 3-methylthiophenyl isocyanate is made by reacting 3-methylthioaniline with phosgene.ALSO:Herbicidal compositions comprise a compound of formula <FORM:0978860/A5-A6/1> (R is a saturated or unsaturated C1-4-aliphatic hydrocarbon radical, optionally halogenated, X and X1 are each O or S) in admixture with at least one of the following: solid carriers, emulsifiers of the non-ionic, cationic or anionic type, dispersing agents, distributing agents, adhesives, solvents, fertilizers, e.g. superphosphate or urea or other herbicides or pest-combating agents. A number of the usual additives are mentioned. Other herbicides may be halogenated phenoxyalkane carboxylic acids, halogenated benzoic or phenylacetic acids or the corresponding nitriles; halogenated fatty acids or their salts, esters and guides; dodecylhexamethyleneimine or salts thereof or 1,11-ethylene dipyridinium bromide; triazine derivatives, 2-chlorobenzothiazole, 3-amino-1,2,4-triazole, maleic acid hydrazide or 3 : 5-dimethyltetrahydro - 1,3,5 - thiodiazine - 2 - thione; pentachlorophenol, dinitrocresol, dinitrobutylphenol or naphthylphthalamic acid. The use of N-p-(4-chlorophenoxy) phenyl-N,N1-dimethylurea together with e.g. isopropyl 3-methoxycarbasilate is specified (Example 6); other compositions are also described. Specified forms are emulsions, pastes, wettable powders, solutions, granules and dusts.