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Pest Manag Sci

Title:		Electrophilic derivatives antagonise pheromone attraction in Cydia pomonella
Author(s):		Sans A; Gago R; Mingot A; Garcia W; Bosch D; Coll J; Rosell G; Bosch MP; Riba M; Guerrero A;
Address:		"University of Lleida, Centre UdL-IRTA, Lleida, Spain"
Journal Title:		Pest Manag Sci
Year:		2013
Volume:		20130403
Issue:		11
Page Number:		1280 - 1290
DOI:		10.1002/ps.3500
ISSN/ISBN:		1526-4998 (Electronic) 1526-498X (Linking)
Abstract:		"BACKGROUND: Pheromone antagonists are good disruptants of the pheromone communication in insects and, 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"
Keywords:		Animals Dodecanol/*analogs & derivatives/antagonists & inhibitors/chemical synthesis/chemistry/pharmacology Female Male Moths/*drug effects/*physiology Sex Attractants/antagonists & inhibitors/chemical synthesis/chemistry/*pharmacology Cydia pomonella cod;
Notes:		"MedlineSans, Albert Gago, Rafael Mingot, Ares Garcia, Wanda Bosch, Dolors Coll, Josep Rosell, Gloria Bosch, M Pilar Riba, Magi Guerrero, Angel eng Research Support, Non-U.S. Gov't England 2013/04/05 Pest Manag Sci. 2013 Nov; 69(11):1280-90. doi: 10.1002/ps.3500. Epub 2013 Apr 3"