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Synthesis and Insecticidal Activities of Novel N-Sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-Alkoxysulfenate Derivatives

Zhao, Q., Shang, J., Liu, Y., Wang, K., Bi, F., Huang, R., Wang, Q.
Journal of agricultural and food chemistry 2007 v.55 no.23 pp. 9614-9619
hydrazines, insecticides, synthesis, chemical structure, insect growth regulators, insecticidal properties, bioassays, Mythimna separata, Spodoptera exigua, Ostrinia furnacalis, toxicity
A series of novel N-alkoxysulfenyl-N'-tert-butyl-N,N'-diacylhydrazines were designed and synthesized as insect growth regulators by the key intermediates N-chlorosulfenyl-N'-tert-butyl-N,N'-diacylhydrazines, which were prepared for the first time. Compared to N'-tert-butyl-N,N'-diacylhydrazines, these N-alkoxysulfenyl derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the new compounds were evaluated. The results of bioassays showed that the title compounds possessed a combination of strong stomach as well as contact poison property higher than the corresponding parent compounds. In particular, N-methoxysufenyl-N'-tert-butyl-N-4-ethylbenzoyl-N'-3,5-dimethylbenzoylhydrazide (IIIf) as a field testing candidate has higher stomach toxicities against oriental armyworm and beet armyworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIf exhibits higher contact activities against oriental armyworm, Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992. The sulfenyl substituent was essential for high larvacidal activity.