Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system

J Agric Food Chem. 2009 Feb 11;57(3):951-7. doi: 10.1021/jf803305f.

Abstract

To replace nitromethylene pharmacophore with a nitroconjugated system, a series of novel neonicotinoid analogues bearing five-membered aromatic heterocycles were designed and synthesized. Bioassays indicated that some of the synthesized compounds exhibited higher insecticidal activities than imidacloprid against cowpea aphids ( Aphis craccivora ), armyworm ( Pseudaletia separate Walker), Nephotettix bipunctatus (Fabricius), and small brown rice planthopper ( Laodelphasx striatellus ). Exhilaratingly, the activity levels of derivatives 13a and 13j rivaled that of imidacloprid.

Publication types

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

MeSH terms

  • Anabasine / chemistry*
  • Animals
  • Aphids
  • Drug Design
  • Hemiptera
  • Imidazoles
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Moths
  • Neonicotinoids
  • Nitro Compounds / chemistry*
  • Receptors, Nicotinic

Substances

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