Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 2. N-substituted phenoxysulfenate derivatives.

Qiqi Zhao, Jian Shang, Zhiqiang Huang, Kaiyun Wang, Fuchun Bi, Runqiu Huang, Qingmin Wang

Index: J. Agric. Food Chem. 56(13) , 5254-9, (2008)

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Abstract

A series of novel N-substituted phenoxysulfenyl- N'- tert-butyl- N, N'-diacylhydrazines were designed and synthesized as insect growth regulators via the key intermediates N-chlorosulfenyl- N'- tert-butyl- N, N'-diacylhydrazines. Compared to the parent compounds, these N-substituted phenoxysulfenyl 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-(4-chlorophenoxy)sulfenyl -N'- tert-butyl- N-4-ethylbenzoyl- N'-3,5-dimethylbenzoylhydrazide ( IIIi) as a field testing candidate has higher stomach toxicities against oriental armyworm and tobacco cutworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIi exhibits higher contact activities against Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992.