Synthesis and Insecticidal Activities of Novel N-Sulfenyl-N′-tert-butyl-N,N′-diacylhydrazines. 3. N-(Alkyldithio), N-(Aminothio), and N,N-Dithio Derivatives

Abstract

A series of novel N-(alkyldithio) and N-aminothio derivatives of 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. A series of novel N,N-dithio derivatives were also designed and synthesized with N'-tert-butyl-N,N'-diacylhydrazines and sulfur chloride in the presence of sodium hydride. Compared to the parent compounds, these derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that the target compounds possessed comparable activities against oriental armyworm with the corresponding parent compounds. In particular, N-(morpholinosulfenyl)-N'-tert-butyl-N-4-ethylbenzoyl-N'-3,5-dimethylbenzoylhydrazide (IIIk) has higher toxicities against oriental armyworm and diamondback moth than the parent compound, RH-5992.