Synthesis and insecticidal evaluation of novel N-(S-amino)sulfenylated derivatives of diacylhydrazines.
A series of new N-(S-amino)sulfenylated derivatives of diacylhydrazines were synthesized by the reaction of S-aminosulfenyl chlorides with N-tert-butyl-N'-benzoyl-N-substituted benzoylhydrazines in the presence of sodium hydride, and evaluated for moulting hormone mimicking activity. In the course of syntheses, N-N bond cleavage in diacylhydrazines was found and the reaction was studied in some detail. The results of bioassay showed that the title compounds exhibit excellent larvicidal activity. Toxicity assays indicated that these compounds can induce a premature, abnormal and lethal larval mount.
Wang
Qingmin
Q
Research Institute of Elemento-Organic Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China. wang98h@263.net
Cheng
Junran
J
Huang
Runqin
R
D000818:Animals; D001549:Benzamides / Q000138:chemical synthesis / Q000633:toxicity*; D001681:Biological Assay; D006834:Hydrazines / Q000138:chemical synthesis / Q000633:toxicity*; D007313:Insecta / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis / Q000378:metabolism / Q000633:toxicity*; D007814:Larva / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D001549:Benzamides; D006834:Hydrazines; D007306:Insecticides