title: Antagonism of pheromone response of Ostrinia nubilalis males and implications on behavior in the laboratory and in the field.
abstract: The antagonistic effect on the pheromone response and catabolism of male European corn borers, Ostrinia nubilalis, by several trifluoromethyl ketones is reported. (Z)-11-Tetradecenyl trifluoromethyl ketone (Z11-14:TFMK), the most closely related analogue of the main component of the pheromone, elicits a remarkable disruptive effect on close approach and source contact of males flying to a source baited with mixtures of the pheromone and the antagonist in 5:1 and 10:1 ratios. In this experiment, the male displayed an erratic flight track with frequent counter turns and intersections with the plume. In the field, the TFMK significantly lowered the number of males caught when mixed with the pheromone in a 10:1 ratio in comparison with the natural attractant. The compound was also a good inhibitor of the antennal esterase of the insect with a IC(50) value of 0.28 muM. The homologous (Z)-10-tridecenyl trifluoromethyl ketone, with one carbon less in the chain, also elicited an antagonistic effect in the wind tunnel, but in the field, the results were not conclusive. The effect induced was lower than the one displayed by Z11-14:TFMK including the activity as the esterase inhibitor (IC(50) value of 7.55 muM). The saturated tetradecyl trifluoromethyl ketone, tetradecyltrifluoropyruvamide, and (Z)-11-2-thiatetradecenyl trifluoromethyl ketone resulted completely inactive. The results obtained in conjunction to the previously shown low toxicity to mice by related trifluoromethyl ketones provide new important data for the putative utilization of these chemicals as new pest control agents.
authors.affiliation: Universitat de Lleida, Centre UdL-IRTA, Rovira Roure 177, 25198 Lleida, Spain. mriba@quimica.udl.es
authors.forename: Magi
authors.initials: M
authors.lastname: Riba
authors.forename: Albert
authors.initials: A
authors.lastname: Sans
authors.forename: Joan
authors.initials: J
authors.lastname: Solé
authors.forename: Lourdes
authors.initials: L
authors.lastname: Muñoz
authors.forename: M Pilar
authors.initials: MP
authors.lastname: Bosch
authors.forename: Gloria
authors.initials: G
authors.lastname: Rosell
authors.forename: A
authors.initials: A
authors.lastname: Guerrero
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects*; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004950:Esterases / Q000037:antagonists & inhibitors; D007306:Insecticides; D007659:Ketones / Q000494:pharmacology*; D008297:Male; D009036:Moths / Q000502:physiology*; D010675:Pheromones / Q000037:antagonists & inhibitors*
chemical_list: C480312:11-hexadecenyl trifluoromethyl ketone; D004791:Enzyme Inhibitors; D007306:Insecticides; D007659:Ketones; D010675:Pheromones; D004950:Esterases