The Absolute Configuration of the Sex Pheromone of the Citrophilous Mealybug, Pseudococcus calceolariae

C. Rikard Unelius, Ashraf M. El-Sayed, Andrew Twidle, Barry Bunn, Tania Zaviezo, M. Fernanda Flores, Vaughn Bell, JAN BERGMANN

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae, was determined to be (1R,3R)-[2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl (R)-2-acetoxy-3-methylbutanoate. NMR, derivatization reactions, chiral gas chromatography-mass spectrometry, and comparison with synthetic chiral reference compounds, were used to determine the absolute configuration of this compound. This activity of this compound was further confirmed by testing synthetic stereoisomers of the compound as lures in traps for adult male mealybugs. Traps baited with 1,000 μg of the pheromone compound caught 36 times more males than traps baited with virgin females. A mixture of stereoisomers of the pheromone compound can be used for field trapping without adverse effects on trap catch. A comparison with the structures of other sex pheromones of mealybugs is presented.

Original languageEnglish
Pages (from-to)166-172
Number of pages7
JournalJournal of Chemical Ecology
Volume37
Issue number2
DOIs
StatePublished - 1 Feb 2011

Keywords

  • (R,R,R)-Chrysanthemyl 2-acetoxy-3-methylbutanoate
  • (R,R,R)-chrysanthemyl 2-hydroxy-3-methylbutanoate
  • Chrysanthemol
  • Mealybug pheromone
  • Pseudococcus calceolariae

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