Synthesis and pheromonal activity of 6,10,13-trimethyl-1-tetradecanol for predatory stink bug,Stiretrus anchorago (Heteroptera: Pentatomidae)

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Abstract
Racemic 6,10,13-trimethyl-1-tetradecanol has been synthesized. Successive elaboration of the molecule using 5-methyl-2-hexanone as the carbon-terminal fragment gave the desired alcohol in a 4% overall yield over 13 steps. Neglecting stereochemistry, the product was shown to be identical to the alcohol previously identified from the sternal glands of maleStiretrus anchorago. It attracts both adult sexes and larvae of this insect in the field, confirming its postulated identity as an aggregation pheromone. The corresponding aldehyde is more than 10 times more concentrated in airbornetrapped samples (5–7% by gas chromatography) than in extracts of glandular setae (0.4–0.5%). This alcohol or its isovalerate ester has been found in other predaceous pentatomids, providing further evidence for pheromones in these species.