Female sex pheromone of Cameraria ohridella Desch. and Dim. (Lepidoptera: Gracillariidae): structure confirmation, synthesis and biological activity of (8E,10Z)-8,10-tetradecadienal and some analogues

Z Naturforsch C J Biosci. 2002 Jul-Aug;57(7-8):739-52. doi: 10.1515/znc-2002-7-832.

Abstract

Mass spectrometric investigations confirmed the structure of the female produced sex pheromone of the horse-chestnut leafminer Cameraria ohridella Desch. and Dim. to be (8E,IOZ)-8,10-tetradecadienal. Pure samples, prepared in a straightforward synthesis, were highly attractive in field tests and proved to be suitable for monitoring of flight activities and population dynamics. In mixtures with the synthetic pheromone, analogues like 9-tridecynal and 7-dodecynyl formate were shown to reduce trap catches. In electroantennographic experiments, pheromone analogues were less active than the pheromone. 9-Tridecynal was the most EAG active analogue tested, followed by 7-dodecyn-1-yl formate and 7-undecyn-1-yl formate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / pharmacology*
  • Animals
  • Chromatography, Gas
  • Female
  • Models, Molecular
  • Molecular Structure
  • Moths / drug effects
  • Moths / physiology*
  • Plant Leaves / parasitology
  • Sex Attractants / chemistry*
  • Sex Attractants / isolation & purification
  • Sex Attractants / pharmacology
  • Structure-Activity Relationship

Substances

  • 8,10-tetradecadienal
  • Aldehydes
  • Sex Attractants