Affinity to the nicotinic acetylcholine receptor and insecticidal activity of chiral imidacloprid derivatives with a methylated imidazolidine ring

Biosci Biotechnol Biochem. 2011;75(4):780-2. doi: 10.1271/bbb.100846. Epub 2011 Apr 22.

Abstract

Four imidacloprid derivatives with an asymmetrically methylated imidazolidine ring were synthesized. Their affinity to the nicotinic acetylcholine receptor of housefly Musca domestica and insecticidal activity against the housefly were measured. The compound with a 5R-methylated imidazolidine ring demonstrated intrinsic activity comparable to that of the unsubstituted compound. Most of the compounds were synergized by oxygenase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Houseflies
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Imidazoles / metabolism*
  • Imidazolines / chemistry*
  • Insecticides / chemical synthesis
  • Insecticides / chemistry*
  • Insecticides / metabolism*
  • Methylation
  • Neonicotinoids
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry*
  • Nitro Compounds / metabolism*
  • Protein Binding
  • Receptors, Nicotinic / metabolism*
  • Stereoisomerism

Substances

  • Imidazoles
  • Imidazolines
  • Insecticides
  • Neonicotinoids
  • Nitro Compounds
  • Receptors, Nicotinic
  • imidacloprid