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 aniline s with chloroformates. Their biological activities were investigated. The compounds with 3-isopropyl group in phenyl ring were found to be a ctive in herbicidal action to weeds and the cyclohexyl ester was the m ost active amoung them. The compounds with 3-OH group in phenyl ring w ere 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 t heir herbicidal activity was investigated. All the compounds were foun d to have herbicidal activities to weeds and the compounds with 3-isop ropyl group in phenyl ring were the most active.