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Chemical Senses 19: 1-10,
© 1994

research-article

Trifluoromethyl ketones as inhibitors of the processionary moth sex pheromone1

A. Parrilla and A. Guerrero

Department of Biological Organic Chemistry C.I.D. (CSIC) Jordi Girona Salgado, 18-26, 08034 Barcelona, Spain

Aliphatic and aromatic trifluoromethyl ketones have been evaluated in the laboratory and in the field as inhibitors of the pheromone response of the processionary moth Thaumetopoea pityocampa males. Among them, two compounds, (Z)-l, l, l-trifluoro-15-octadecen-13-yn-2-one and (Z)-l, l, l-trifluoro-16-nonadeceo-14-yn-2-one, are closely related analogs of the natural pheromone (Z)-13-hexadecen-11-ynyl acetate. In the laboratory experiments, carried out by pre-exposure of males to vapors of the chemicals, {alpha}-naphthyl trifluoromethyl ketone, ß-naphthyl trifluoromethyl ketone, l, l, l-trifluorotetradecan-2-one and (Z)-16-nonadecen-14-yn-2-one displayed notable blockage of the pheromone detection on EAG. The activity of l, l, l-trifluorotetradecan-2-one is postulated to be due to the inhibition of the pheromone-degrading esterase. In general, the compounds have shown low specificity for the substrate and exhibited only a modest or null EAG intrinsic activity. In the field, benzyl trifluoromethyl ketone, trifluoroacetophenone, (Z)-l, l, l-trifluoro-15-octadecen-13-yn-2-one, (Z)-l, l, l-trifluoro-16-nonadecen-14-yn-2-one and ß-naphthyl trifluoroacetate showed a remarkable disruptant effect when mixed with the pheromone in 1:0.1, 1:1 and 1:10 ratio. (Z)-16-Nonadecen-14-yn-2-one has been found to be a modest agonist of the natural pheromone, exhibiting an attractant activity threefold lower than the parent molecule.

1Presented in part at the OILB/WPRS Meeting held in Chatham, Kent, UK, 1993.


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This article has been cited by other articles:


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 Chem SensesHome page
J. Bau, D. Martinez, M. Renou, and A. Guerrero
Pheromone-triggered Orientation Flight of Male Moths can be Disrupted by Trifluoromethyl Ketones
Chem Senses, October 1, 1999; 24(5): 473 - 480.
[Abstract] [Full Text] [PDF]

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 Chem SensesHome page
M. Renou, A. Berthier, L. Desbarats, J. Van der Pers, and A. Guerrero
Actographic Analysis of the Effects of an Esterase Inhibitor on Male Moth Responses to Sex Pheromone
Chem Senses, August 1, 1999; 24(4): 423 - 428.
[Abstract] [Full Text] [PDF]


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