Chemical protection of pheromones containing an internal conjugated diene system from isomerization and oxidation

Rut Ideses, Arnon Shani

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Conjugated diene systems are common in natural products, including pheromones. The systems are sensitive to heat, light, and oxygen, among other things. They can be protected by antioxidants and UV absorbers, which slow down cis-trans isomerization and oxidation. Three sex pheromones (one as an analog) containing Z,E, E,Z, and E,E units were studied: (Z,E)-9,11-C14OAc, (E,Z)-7,9-C12OAc, and (E,E)-10,12-C16OAc. The UV absorber 2-hydroxy-4-methoxybenzophenone and the antioxidants BHT and BHA were found to be effective in solution. The protective effect of the UV absorber against photoisomerization on paper carriers was not as good as that in solution. Preliminary studies on the utilization of formulations containing these compounds and (Z,E)-9,11-C14OAc in the mass trapping of Egyptian cotton leafworm male in cotton fields showed the new combinations to be as good as a previously used formulation with UOP 688, a compound which is unpleasant to handle.

Original languageEnglish
Pages (from-to)1657-1669
Number of pages13
JournalJournal of Chemical Ecology
Volume14
Issue number8
DOIs
StatePublished - 1 Aug 1988

Keywords

  • Earias insulana
  • Lobesia botrana
  • Spodoptera littoralis
  • UV absorbers
  • antioxidants
  • conjugated dienes
  • photoisomerization
  • protection of pheromones
  • sex pheromone

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