Abstract
The behavioral response of processionary males (Thaumetopoea pityocampa) to the natural pheromone (Z)-13-hexadecen-11-ynyl acetate (1) and structurally related analogs in a wind tunnel is presented. Stereomerically pureZ-1 and a mixture with theE isomer in 80:20 ratio elicited similar attraction responses at 1 µg and higher. The activity was dose-dependent, being optimum at 1 µg with 90% and 80% of males contacting with the source in the presence of theZ-1 andZ/E-1, respectively. 11-Hexadecynyl acetate (2) functioned as a pheromone mimic, being able to induce the complete mate-finding behavioral sequence, although its activity was much lower than that of the pheromone. (Z)-13-Hexadecen-11-ynyl alcohol (3) and, particularly, (Z)-13-hexadecen-11-ynal (4) were potent inhibitors of the upwind flight response in mixtures withZ-1 in 99:1, 95:5, and 91:9 ratios. (Z)-1,1,1-Trifluoro-16-nonadecen-14-yn-2-one (5) also inhibited the response of males to pheromone, particularly in the source contact behavior. Comparison with activity displayed by analogs in field tests is also reported.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Albans, K.R., Baker, R., andJones, O.T. 1984. Inhibition of response ofHeliothis virescens to its natural pheromone by antipheromones.Crop Prot. 3:501–506.
Camps, F., Canela, R., Coll, J., Guerrero, A., andRiba, M. 1981a. Synthesis of the two isomers of the potential sex pheromone ofThaumetopoea pityocampa (Lepidoptera, Notodontidae) and related model compounds.Chem. Lett. 1981:703–706.
Camps, F., Coll, J., Guerrero, A., andRiba, M. 1981b. Procedimiento para la preparación por síntesis del acetato de (Z)-13-hexadecen-11-inilo con possible actividad de feromona sexual sobre la procesionaria del pino. Spain Patent 502990.
Camps, F., Coll, J. Guerrero, A., andRiba, M. 1983. Simple and stereoselective synthesis of sex pheromone of processionary mothThaumetopoea pityocampa (Denis and Schiff.).J. Chem. Ecol. 9:869–875.
Camps, F., Gasol, V., Guerrero, A., andLlebaría, A. 1987. Procedimiento para la preparación por síntesis del acetato de (Z)-13-hexadecen-11-inilo y su aplicación como feromona sexual para el control de la procesionaria del pinoThaumetopoea pityocampa. Spain Patent 87800834.
Camps, F., Fabriàs, G., Gasol, V., Guerrero, A., Hernández, R., andMontoya, R. 1988. Analogs of the sex pheromone of processionary mothThaumetopoea pityocampa: Synthesis and biological activity.J. Chem. Ecol. 14:1331–1346.
Camps, F., Gasol, V., andGuerrero, A. 1990a. Inhibitory pheromonal activity promoted by sulfur analogs of the processionary mothThaumetopoea pityocampa (Denis and Schiff.).J. Chem. Ecol. 16:1155–1172.
Camps, F., Gasol, V., Guerrero, A., Hernández, R., andMontoya, R. 1990b. Inhibition of the processionary moth sex pheromone by some haloacetate analogues.Pestic. Sci. 29:123–134.
Cardé, R.T. 1984. Chemo-orientation in flying insects, pp. 111–124,in W.J. Bell and R.T. Cardé (eds.). Chemical Ecology of Insects. Chapman and Hall, London.
Corey, E.J., andSchmidt, G. 1979. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media.Tetrahedron Lett. 1979:399–400.
Cuevas, P., Montoya, R., Bellés, X., Camps, F., Coll, J., Guerrero, A., andRiba, M. 1983. Initial field trials with the synthetic sex pheromone of the processionary mothThaumetopoea pityocampa (Denis & Schiff.).J. Chem. Ecol. 9:85–93.
David, C.T. 1982. Competition between fixed and moving stripes in the control of orientation by flyingDrosophila.Physiol. Entomol. 7:151–156.
Durán, I., Parrilla, A., Feixas, J., andGuerrero, A. 1993. Inhibition of antennal esterases of the Egyption armywormSpodoptera littoralis by trifluoromethyl ketones.Bioorg. Med. Chem. Lett. 3:2593–2598.
Einhorn, J., Menassieu, P., Michelot, D., andRiom, J. 1983. Piégeage sexuel de la processionaire du pinThaumetopoea pityocampa Schiff. (Lepidoptera, Notodontidae) par des attractifs de synthèse. Premiers essais dans le Sud-Ouest de la France.Agronomie 3:499–505.
Gasol, V. 1988. Síntesis y actividad biológica de inhibidores de la feromona sexual de la processionaria del pinoThaumetopoea pityocampa. Relacions estructura-actividad. PhD thesis, Institut Químic de Sarriá, University Ramón Llull (Barcelona).
Guerrero, A., Camps, F., Coll, J., Riba, M., Einhorn, J., Descoins, C., andLallemand, J.Y. 1981. Identification of a potential sex pheromone of the processionary mothThaumetopoea pityocampa.Tetrahedron Lett. 22:2013–2016.
Klun, J.A., Schwarz, M., andUebel, E.C. 1991. European corn borer: Pheromonal catabolism and behavioral response to sex pheromone.J. Chem. Ecol. 17:317–334.
Linderman, R.J., Leazer, J., Roe, R.M., Venkatesh, K., Selinsky, B.S., andLondon, R.E. 1988.19F NMR Spectral evidence that 3-octylthio-1,1,1-trifluoropropan-2-one, a potent inhibitor of insect juvenile hormone esterase, functions as a transition state analog inhibitor of acetylcholinesterase.Pestic. Biochem. Physiol. 31:187–194.
Mafra-Neto, A., andCardé, R.T. 1994. Fine-scale structure of pheromone plumes modulates upwind orientation of flying moths.Nature 369:142–144.
Michelot, D., Guerrero, A., andRatovelomanana, V. 1982. Une synthèse courte et stéréo-selective de l'acetoxyl-l-hexadécène-13(Z)-yne-11: Principal constituant de la secretion phéromonale produite par la femelle vierge de la processionaire du pinThaumetopoea pityocampa (Denis and Schiff) (Lepidoptera, Notodontidae).J. Chem. Res. (S) 1982:93.
Miller, J.R., andRoelofs, W.L. 1978. Sustained-flight tunnel for measuring insect responses to windborne sex pheromones.J. Chem. Ecol. 4:187.
Montoya, R., andHernández, R. 1991. La procesionaria del pino, pp. 59–73,in Miniserio de Agricultura (ed.). Plagas de insectos en las masas forestales españolas. ICONA, Madrid.
Parrilla, A. 1994. Estudios sobre mediadores químicos con actividad sobre el comportamiento de insectos. PhD thesis, University of Barcelona.
Parrilla, A., andGuerrero, A. 1994. Trifluoromethyl ketones as inhibitors of the processionary moth sex pheromone.Chem. Senses 19:1–10.
Parrilla, A., Villuendas, I., andGuerrero, A. 1994. Synthesis of trifluoromethyl ketones as inhibitors of antennal esterases of insects.Bioorg. Med. Chem. 2:243–252.
Preiss, R., andPriesner, E. 1988. Responses of male codling moths (Laspeyresia pomonella) to codlemone and other alcohols in a wind tunnel.J. Chem. Ecol. 14:797–813.
Prestwich, G.D. 1987. Chemistry of pheromone and hormone metabolism in insects.Science 237:999–1006.
Quartey, G.K., andCoaker, T.H. 1993. Role of sex pheromone components in the orientation behaviour ofEphestia cautella.Entomol. Exp. Appl. 66:237–245.
Schwarz, M., Klun, J.A., andUebel, E.C. 1990. European corn borer sex pheromone. Inhibition and elicitation of behavioral response by analogs.J. Chem. Ecol. 16:1591–1604.
Sokal, R.R., andRohlf, F.G. (eds.). 1969. Biometry. Freeman, San Francisco.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Quero, C., Camps, F. & Guerrero, A. Behavior of processionary males (Thaumetopoea pityocampa) induced by sex pheromone and analogs in a wind tunnel. J Chem Ecol 21, 1957–1969 (1995). https://doi.org/10.1007/BF02033855
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02033855