Synthesis and insecticidal efficacy of pyripyropene derivatives focusing on the C-1, C-7, and C-11 positions' substituent groups

J Antibiot (Tokyo). 2018 Sep;71(9):785-797. doi: 10.1038/s41429-018-0064-9. Epub 2018 May 23.

Abstract

The C-1, C-7, and C-11 positions of pyripyropene A were chemically modified to improve the insecticidal activity. Some derivatives showed higher insecticidal activities against aphids than pyripyropene A. In particular, the derivative 5c, which possesses three cyclopropyl carbonyl groups at the C-1, C-7, and C-11 positions, had excellent insecticidal activity levels in field and laboratory trials.

MeSH terms

  • Animals
  • Aphids / drug effects*
  • Aspergillus fumigatus / metabolism
  • Insecticides / chemical synthesis*
  • Insecticides / pharmacology*
  • Mice
  • Penicillium / metabolism
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Rats
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology*

Substances

  • Insecticides
  • Pyridines
  • Sesquiterpenes
  • pyripyropene A