Synthesis and Biological Activities of Phenylcarbamates and Phenylthiocarbamates

Abstract

Various kinds of alkyl phenylcarbamates (Substituents in phenyl ring =3-i-Pr, 4-i-Pr, 3-isopropenyl, 2-OH, 3-OH, 4-OH, 4-(p-chlorophenoxy), 2-Me-5-i-Pr, and 2, 6-(i-Pr)2)were prepared by the reaction of anilines with chloroformates. Their biological activities were investigated. The compounds with 3-isopropyl group in phenyl ring were found to be active in herbicidal action to weeds and the cyclohexyl ester was the most active amoung them. The compounds with 3-OH group in phenyl ring were also found to be active in hypnotics. S-Alkyl phenylthiocarbamates (Alky1=Et, Pr, i-Pr, Bu, i-Bu, and s-Bu; substituents in phenyl ring = H, 3-Me, 4-Me, 4-Me(); 3-i-Pr, 3-i-PrO, 3-isopropenyl, 2, 6-(i-Pr)2, 4-OH, 4-C1, and 4-NO2) were prepared mainly by the reaction of anilines with carbonyl sulfid e and alkyl bromides in the presence of BuLi and their herbicidal activity was investigated. All the compounds were found to have herbicidal activities to weeds and the compounds with 3-isopropyl group in phenyl ring were the most active.727