SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF PHENYLCARBAMATES AND PHENYLTHIOCARBAMATES

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 (Alkyl=Et, Pr, i-Pr, Bu, i-Bu, and s-Bu ; substituents in phenyl ring=H, 3-Me, 4-Me, 4-MeO; 3-i-Pr, 3-i-PrO, 3-isopropenyl, 2,6-(i-Pr)2, 4-OH, 4-Cl, and 4-NO2) were prepared mainly by the reaction of anilines with carbonyl sulfide 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.