Synthesis, crystal structure and biological activity of aryl [(N,N'-diacyl-N'-tert-butylhydrazino)thio]methylcarbamates

A series of novel aryl (N,N'-diacyl-N'-tert-butylhydrazino)thio]methylcarbamates were synthesized by the reaction of aryl (chlorothio)methylcarbamates with N,N'-diacyl-N-tert-butylhydrazines in the presence of sodium hydride. X-Ray single crystal diffraction of 2-isobutylphenyl (N,N'-dibenzoyl-N'-tert-butylhydrazino)thio]methylcarbamate demonstrated the presence of N-S-N bonding. All of the compounds exhibited excellent larvicidal activities. Toxicity assays indicated that the products had knockdown activities of aryl methylcarbamates at higher concentrations and insect growth regulator activities of diacylhydrazines at lower concentrations.