Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-alkoxysulfenate derivatives |
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Authors: | Zhao Qiqi Shang Jian Liu Yuxiu Wang Kaiyun Bi Fuchun Huang Runqiu Wang Qingmin |
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Affiliation: | State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China. |
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Abstract: | 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. |
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