cis-Configuration: a new tactic/rationale for neonicotinoid molecular design

J Agric Food Chem. 2011 Apr 13;59(7):2943-9. doi: 10.1021/jf103499x. Epub 2010 Nov 2.

Abstract

Resistance development and limited lepidopteran activities call for the discovery of "super-neonicotinoids" solving these problems. Compounds with the cis-configuration offer an opportunity for further optimization. Fixing the nitro group in the cis-configuration provided a new approach for neonicotinoid molecular design. Introductions of the heterocycle or a bulky group are two synthesis concepts to fix the cis-configuration of the nitro group. The design, synthesis, bioactivity, and preliminary modes of action of five types of cis-neonicotinoids are reviewed. cis- and trans-neonicotinoids have some differences in bioactivities and modes of action. This study focused, especially, on the reaction diversities of nitromethylene analogues of imidacloprid with various aldehydes.

Publication types

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

MeSH terms

  • Anabasine / agonists*
  • Animals
  • Drug Design
  • Imidazoles
  • Insecticide Resistance
  • Insecticides / chemistry*
  • Lepidoptera
  • Molecular Conformation
  • Neonicotinoids
  • Nitro Compounds
  • Structure-Activity Relationship

Substances

  • Imidazoles
  • Insecticides
  • Neonicotinoids
  • Nitro Compounds
  • imidacloprid
  • Anabasine