Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer

J Chem Ecol. 2003 Oct;29(10):2189-99. doi: 10.1023/a:1026210111334.

Abstract

It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Female
  • Hymenoptera / chemistry*
  • Insect Control
  • Male
  • Movement
  • Sex Attractants / chemical synthesis
  • Sex Attractants / chemistry*
  • Sex Attractants / pharmacology*

Substances

  • Sex Attractants