Synthesis, spectroscopy and biological activity of novel acylhydrazines containing ferrocenyl moiety

In a search for new insect growth regulators, we replaced the phenyl moiety by ferrocenyl in N-tert-butyl-N,N′-dibenzoylhydrazine and synthesized the novel N-tert-butyl-N′-ferrocenoyl-N-substitutedbenzoylhydrazines by the reaction of ferrocenoyl chloride with N-tert-butyl-N-substituted benzoylhydrazines in dry tetrahydrofuran using triethylamine as the acid acceptor. The N-tert-butyl-N-ferrocenoyl-N′-substituted benzoylhydrazines were prepared similarly. Then, the treatment of N-tert-butyl-N′-ferrocenoyl-N-benzoylhydrazine with alkylmethyl(chlorosulfenyl)carbamates in the presence of sodium hydride afforded the novel acylhydrazines containing the ferrocenyl moiety. The title compounds were identified by IR spectroscopy, 1H-NMR spectroscopy, EIMS and elemental analyses. The results of bioassay showed that some of the title compounds exhibit excellent larvicidal activities. Toxicity assays indicated that the title compounds could induce a premature, abnormal and lethal larval molt. We found by chance that one of the title compounds possesses good anti-TMV (Tobacco Mosaic Virus) activity.