HERBICIDALLY-ACTIVE SUBSTITUTED PHENYL-THIOCARBAMATES AND THEIR MANUFACTURE AND USE

摘要

1369491 Substituted phenylthiocarbamates SCHERING AG 27 Sept 1971 [24 Nov 1970] 44945/71 Heading C2C Substituted phenylthio carbamates of the general formula in which R 1 represents a C 1-5 alkyl group and R 2 represents a phenyl, alkylphenyl, alkoxyphenyl, alkylthiophenyl or halogenophenyl group are prepared by (a) reacting a compound of the general formula in the presence of an inorganic or organic base with an amine of the formula or (b) reacting a compound of the general formula: or salt thereof in the presence of an inorganic or organic base with a carbamoyl chloride of the general formula or (c) catalytically reducing a compound of the general formula to the corresponding amine and reacting this with a compound CH 3 -S-CO-Cl. Compounds claimed per se are S-methyl-N-[3-(N1-methyl- N1 - phenylcarbamoyloxy)- phenyl] - thiocarbamate; S - methyl - N - {3 - [N1 - methyl - N1- (41 - ethylphenyl) - carbamoyloxy} - phenyl}- thiocarbamate; S - methyl - N - {3 - [N1 - ethyl- N1 - (41 - methylphenyl) - carbamoyloxy]- phenyl} - thiocarbamate; S - methyl - N - [3- (N1 - ethyl - N1 - phenylcarbamoyloxy) - phenyl] - thiocarbamate; S - methyl - N - {3 - [N1- ethyl - N1 - (31 - methylphenyl) - carbamoyl]- phenyl} - thiocarbamate; S - methyl - N - {3- [N1 - ethyl - N1 - (21 - methylphenyl) - carbamoyloxy]-phenyl}-thiocarbamate; S-methyl- N - [3 - (N1 - isopropyl - N1 - phenyl - carbamoyloxy) - phenyl] - thiocarbamate; S - methyl - N- {3 - [N1 - methyl - N1 - (31 - methylphenyl)- carbamoyloxy]-phenyl}-thiocarbamate. The compounds have herbicidal properties. The chloroformic acid-3-methyl-mercapto carbamoyl aminophenyl ester used as starting material was prepared from the 3-hydroxythio carbanilic acid-S-methyl ester and phosgene with the addition of dimethyl aniline in ethyl acetate.