Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 2. N-substituted phenoxysulfenate derivatives

J Agric Food Chem. 2008 Jul 9;56(13):5254-9. doi: 10.1021/jf800740z. Epub 2008 Jun 10.

Abstract

A series of novel N-substituted phenoxysulfenyl- 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. Compared to the parent compounds, these N-substituted phenoxysulfenyl 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-(4-chlorophenoxy)sulfenyl -N'- tert-butyl- N-4-ethylbenzoyl- N'-3,5-dimethylbenzoylhydrazide ( IIIi) as a field testing candidate has higher stomach toxicities against oriental armyworm and tobacco cutworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIi exhibits higher contact activities against Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Assay
  • Hydrazines / chemical synthesis*
  • Hydrazines / chemistry
  • Hydrazines / toxicity*
  • Hydrophobic and Hydrophilic Interactions
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / toxicity*
  • Molecular Structure
  • Moths / drug effects*
  • Stomach / drug effects
  • Structure-Activity Relationship

Substances

  • Hydrazines
  • Insecticides
  • N,N'-diacetylhydrazine