The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae.
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.
The New Zealand Institute for Plant & Food Research Ltd, Canterbury Research Centre, Lincoln, New Zealand. rikard.unelius@lnu.se
C Rikard
CR
Unelius
Ashraf M
AM
El-Sayed
Andrew
A
Twidle
Barry
B
Bunn
Tania
T
Zaviezo
M Fernanda
MF
Flores
Vaughn
V
Bell
Jan
J
Bergmann
D000818:Animals; D020148:Butyric Acid / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006430:Hemiptera / Q000737:chemistry* / Q000187:drug effects; D008297:Male; D012724:Sex Attractants / Q000737:chemistry* / Q000494:pharmacology; D012726:Sexual Behavior, Animal / Q000187:drug effects; D013237:Stereoisomerism
D012724:Sex Attractants; D020148:Butyric Acid
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