Journal of Chemical Ecology (1995) 21, 849-858
Ezra Dunkelblum, Regine Gries, Gerhard Gries, Kenji Mori and Zvi Mendel (1995)
Chirality of israeli pine bast scale, Matsucoccus josephi (Homoptera: Matsucoccidae) sex pheromone
Journal of Chemical Ecology 21 (6), 849-858
Abstract: The absolute configuration of the sex pheromone of the Israeli pine bast scale, Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here as R-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated as S-E. The chirality of the quantitatively minor Z isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of natural M. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemic Z andE isomers, the latter elicited the stronger antennal response by male M. josephi. In GC-EAD of all four stereoisomers, employing the chiral column, R-E was the most active stereoisomer. In field tests R-E attracted 10 times more males of M. josephi than did S-E. The racemic E/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many male M. josephi as did an equivalent amount of R-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship.
(The abstract is excluded from the Creative Commons licence and has been copied with permission by the publisher.)
Link to article at publishers website
Database assignments for author(s): Gerhard Gries, Zvi Mendel
Research topic(s) for pests/diseases/weeds:
pheromones/attractants/traps
Pest and/or beneficial records:
Beneficial | Pest/Disease/Weed | Crop/Product | Country | Quarant.
|
---|---|---|---|---|
Matsucoccus josephi |