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Electrophilic derivatives antagonise pheromone attraction in cydia pomonella

AuthorsSans, Albert; Gago, Rafael ; Mingot, A. ; García, Wanda; Bosch, Dolors; Coll, Josep C.; Rosell, Glòria; Bosch, María Pilar ; Riba, Magí V.; Guerrero, Angel
KeywordsCodling moth
Cydia pomonella
Pest control
Pheromone analogues
Pheromone antagonists
Issue Date4-Jun-2015
AbstractPheromone antagonists are good disruptants of the pheromone communication in insects as such, have been used in mating disruption experiments. In this study, new non-fluorinated electrophilic keto derivatives structurally related to the pheromone of Cydia pomonella (codlemone) have been synthesised and tested as putative pheromone antagonists. RESULTS: Codlemone (1) was prepared in excellent stereoselectivity in a new, iterative approach involving two Horner-Wadsworth-Emmons reactions. Methyl ketone (2), keto ester (3) and diketone (4) were obtained from codlemone in straightforward approaches in good overall yields and excellent stereochemical purity (≥98% E,E). In electrophysiology, only compound 2 displayed inhibition of the antennal response to the pheromone after presaturation of the antennal receptors. Compounds 2 to 4 did not inhibit the pheromone-degrading enzyme responsible for codlemone metabolism, but mixtures of ketone 2 and diketone 4 with codlemone elicited erratic flights on males in a wind tunnel. In the field, blends of either compound (2 or 4) with the pheromone caught significantly fewer males than codlemone alone. CONCLUSION: Codlemone and the potential antagonists 2 to 4 have been synthesised in good yields and excellent stereoselectivity. These chemicals behave as pheromone antagonists of the codling moth both in the laboratory and in the field.
Publisher version (URL)10.1002/ps.3500
Appears in Collections:(IQAC) Artículos
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