Difluoropalmitic acids as potential inhibitors of the biosynthesis of the sex pheromone of the Egyptian armyworm Spodoptera littoralis--IV

Bioorg Med Chem. 1996 Mar;4(3):467-72. doi: 10.1016/0968-0896(96)00027-2.

Abstract

2,2-, 3,3- and 4,4-Difluoropalmitic acids (1-3) have been synthesized and fully characterized. Acids 2 and 3 were prepared through fluorination of the corresponding dithioacetal-protected ketoesters followed by enzymatic saponification. The acids 1-3 were evaluated in vivo as inhibitors of the beta-oxidation step of the biosynthesis of (Z,E)-9,11-tetradecadienyl acetate, the major component of the sex pheromone of the Egyptian armyworm Spodoptera littoralis. Only, the 2,2- and 3,3-derivatives, i.e. those containing the two fluorine atoms at the positions involved in the chain-shortened step, have been found to be active, the activity being similar to or lower than that displayed by the corresponding monofluorinated acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Esters / metabolism
  • Fatty Acids / metabolism
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Palmitic Acids / pharmacology*
  • Sex Attractants / antagonists & inhibitors
  • Sex Attractants / biosynthesis*
  • Spectroscopy, Fourier Transform Infrared
  • Spodoptera / drug effects
  • Spodoptera / metabolism*

Substances

  • 2,2-difluoropalmitic acid
  • 3,3-difluoropalmitic acid
  • 4,4-difluoropalmitic acid
  • Esters
  • Fatty Acids
  • Palmitic Acids
  • Sex Attractants