TY - JOUR
T1 - The Absolute Configuration of the Sex Pheromone of the Citrophilous Mealybug, Pseudococcus calceolariae
AU - Unelius, C. Rikard
AU - El-Sayed, Ashraf M.
AU - Twidle, Andrew
AU - Bunn, Barry
AU - Zaviezo, Tania
AU - Flores, M. Fernanda
AU - Bell, Vaughn
AU - Bergmann, Jan
N1 - Funding Information:
Acknowledgements This work was supported by the Foundation for Research Science and Technology, FRST (Sustainable Integrated Pest Management in Horticulture, C06X0811) and the Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT grant 11060527). We thank Tom Sullivan (New Zealand) and Alda Romero (Chile) for maintaining mealybug colonies and Lyn Cole for assistance with the New Zealand field trials. Financial funding from the Linnaeus University, Kalmar, is gratefully acknowledged.
PY - 2011/2
Y1 - 2011/2
N2 - 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.
AB - 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.
KW - (R,R,R)-Chrysanthemyl 2-acetoxy-3-methylbutanoate
KW - (R,R,R)-chrysanthemyl 2-hydroxy-3-methylbutanoate
KW - Chrysanthemol
KW - Mealybug pheromone
KW - Pseudococcus calceolariae
UR - http://www.scopus.com/inward/record.url?scp=79951947203&partnerID=8YFLogxK
U2 - 10.1007/s10886-010-9904-1
DO - 10.1007/s10886-010-9904-1
M3 - Article
C2 - 21243408
AN - SCOPUS:79951947203
SN - 0098-0331
VL - 37
SP - 166
EP - 172
JO - Journal of Chemical Ecology
JF - Journal of Chemical Ecology
IS - 2
ER -