Journal of Chemical Ecology (2006) 32, 2525-2541

Erik Hedenström, Helene Edlund, Ann-Britt Wassgren, Gunnar Bergström, Olle Anderbrant, Fredrik Östrand, Andrzej Sierpinski, Marie-Anne Auger-Rozenberg, Annette Herz, Werner Heitland and Martti Varama (2006)
Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity
Journal of Chemical Ecology 32 (11), 2525-2541
Abstract: We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.
(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): Erik Hedenström, Annette Herz, Olle Anderbrant, Werner Heitland

Research topic(s) for pests/diseases/weeds:
pheromones/attractants/traps

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Pest and/or beneficial records:

Beneficial	Pest/Disease/Weed	Crop/Product	Country	Quarant.
	Gilpinia pallida