Synthesis and insecticidal activities of novel oxime ether pyrethroids

A series of novel 2-methylthio-3'/4'-substituted acetophenone oxime O-ethers were synthesized by the reaction of the corresponding acetophenone oximes with halides of pyrethroid alcohols in the presence of sodium hydroxide and phase-transfer catalysis or with triethyl quaternary ammonium salts of halides of pyrethroid alcohols in the presence of sodium hydroxide. These compounds showed notable insecticidal activity against Homopteran and Lepidopteran pests. 2-Methylthio-4'-fluoroacetophenone oxime O-(2-methylbiphenyl-3-yl)methyl] ether was more effective than the commercial insecticides chlorfenapyr and fenvalerate.