cis-Nitromethylene neonicotinoids as new nicotinic family: synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-alpha]pyridine

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6513-6. doi: 10.1016/j.bmcl.2008.10.048. Epub 2008 Oct 14.

Abstract

A series of neonicotinoids analogues of hexahydroimidazo[1,2-alpha]pyridine were modified at 5-, 6-, and 7-positions, and their insecticidal activities were evaluated. Introducing a methyl or ethyl at 7-position increased the insecticidal activities, while other substituents decreased activities. When alkyl substituents were introduced to 7-position, the insecticidal activities against Pea aphids decreased in the order methyl (7a)>ethyl (7b)>n-butyl (7e)>phenyl (7f)>n-propyl (7c)>iso-propyl (7d), p-NO(2)-phenyl (7g). Modifications at 5-, 6- or both at 6- and 7-positions with methyl or ethyl were unfavorable to activities. Interestingly, introducing methyl to 7-position not only increased insecticidal activities against pea aphids, but also show higher insecticidal activities than imidacloprid against imidacloprid-resistant brown planthopper.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chemistry, Pharmaceutical / methods
  • Crystallography, X-Ray
  • Drug Design
  • Imidazoles / chemical synthesis
  • Imidazoles / pharmacology
  • Insecta
  • Insecticides / chemical synthesis*
  • Insecticides / pharmacology
  • Models, Chemical
  • Molecular Conformation
  • Neonicotinoids
  • Nicotinic Acids / chemistry*
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Receptors, Nicotinic / chemistry*
  • Risk

Substances

  • Imidazoles
  • Insecticides
  • Neonicotinoids
  • Nicotinic Acids
  • Nitro Compounds
  • Pyridines
  • Receptors, Nicotinic
  • imidacloprid