Abstract
Methyl 2,6,10-trimethyltridecanoate (1) and methyl 2,6,10-trimethyldodecanoate (2) have been identified as male-produced sex pheromones of the Brazilian soybean stink bugs Euschistus heros (F.) and Piezodorus guildinii (Westwood). In order to establish a defined attractive blend for both species, compounds 1 and 2 were synthesized as mixtures of stereoisomers to be employed in behavior bioassays. (±)-Citronellol (3) was utilized as starting material, and the syntheses was carried out in six steps with good overall yield. When tested alone, synthetic compounds 1 and 2 proved to be active in a two-choice olfactometer; however, a 20 : 1 mixture of 1 and 2 was much more attractive to E. heros females. A similar blend had been found among the headspace volatiles of males.
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Zarbin, P.H.G., Reckziegel, A., Plass, E. et al. Synthesis and Biological Activity of Methyl 2,6,10-Trimethyldodecanoate and Methyl 2,6,10-Trimethyltridecanoate: Male-Produced Sexual Pheromones of Stink Bugs Euschistus heros and Piezodorus guildinii. J Chem Ecol 26, 2737–2746 (2000). https://doi.org/10.1023/A:1026433608967
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DOI: https://doi.org/10.1023/A:1026433608967