Synthesis and Properties of Pentafluorosulfanyl Group (SF5)-Containing Meta-Diamide Insecticides

Molecules. 2020 Nov 25;25(23):5536. doi: 10.3390/molecules25235536.

Abstract

Herein, we describe novel pentafluorosulfanyl (SF5) group-containing meta-diamide insecticides. For the facile preparation of the SF5-based compounds 4a-d, practical synthetic methods were applied. Among newly synthesized compounds, 3-benzamido-N-(2,6-dimethyl-4-(pentafluoro-λ6-sulfanyl)phenyl)-2-fluorobenzamide 4d showed (i) a high insecticidal activity, (ii) an excellent selectivity to insects, and (iii) good levels of water solubility and log P values. In this study, we demonstrated that the pentafluorosulfanyl moiety could serve as an attractive functionality for the discovery of a new scope of crop-protecting agents.

Keywords: GABARs; insecticide; meta-diamide; pentafluorosulfanyl.

MeSH terms

  • Chemistry Techniques, Synthetic*
  • Diamide / chemical synthesis*
  • Diamide / pharmacology*
  • GABA Antagonists / chemistry
  • GABA Antagonists / pharmacology
  • Insecticides / chemical synthesis*
  • Insecticides / pharmacology*
  • Metals / chemistry*
  • Molecular Structure
  • Receptors, GABA / chemistry
  • Structure-Activity Relationship

Substances

  • GABA Antagonists
  • Insecticides
  • Metals
  • Receptors, GABA
  • Diamide