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  • 1
    Electronic Resource
    Electronic Resource
    Analogs of sex pheromone of processionary moth,Thaumetopoea pityocampa: Synthesis and biological activity (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 1331-1346 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; inhibition ; synergism ; processionary moth ; Thaumetopoea pityocampa ; Lepidoptera ; Thaumetopoeidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The synthesis and biological activity of some analogs of (Z)-13-hexadecen-11-ynyl acetate1, the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The analogs have been formally derived by structural modification of the enyne and acetate functions of the parent compound1. In field tests, trifluoroacetate ester16 and the analog,11, with fluorine substitution at the olefin site, decreased the pheromone action, whereas epoxy derivative,10, from epoxidation of the olefin moiety in1, and propionate ester15 gave synergistic activity. The formate14 had a variable effect according to the composition of the lure. Formal reduction of the enyne to give the acetylene2 was found to retain activity. Alcohols12 and13, resulting from hydrolysis of the enyne1 and acetylene2, respectively, inhibited the action of their parent compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020138
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  • 2
    Electronic Resource
    Electronic Resource
    Inhibitory pheromonal activity promoted by sulfur analogs of the sex pheromone of the female processionary mothThaumetopoea pityocampa (Denis and schiff) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 1155-1172 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; inhibition ; processionary moth ; Thaumetopoea pityocampa ; sulfur analogs ; Lepidoptera ; Thaumetopoeidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract New sulfur analogs of the sex pheromone of the female processionary mothThaumetopoea pityocampa have been found to be effective inhibitors of the natural pheromone activity both in EAG bioassays and field tests. The structures of these analogs have been derived from replacement of the oxygen atom(s) of the acetate group by sulfur (compounds 3-5) and the olefinic moiety of the enyne function by the isosteric SCH2 group (compounds 6 and 7). The synthesis and biological activity of 3-[(Z)-12-pentadecen-10-ynylthio]-1,1,1-trifluoropropan-2-one (8), a closely related structure to the pheromone is also described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021017
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  • 3
    Electronic Resource
    Electronic Resource
    Reinvestigation of Female Sex Pheromone of Processionary Moth (Thaumetopoea pityocampa): No Evidence for Minor Components (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 713-726 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; processionary moth ; Thaumetopoea pityocampa ; Lepidoptera ; Thaumetopoeidae ; minor component ; single cell recording ; behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The female sex pheromone of the processionary moth Thaumetopoea pityocampa has been reinvestigated to look for possible minor components. Examination by GC-MS and GC-EAD of the contents of virgin female glands, after stimulation with PBAN (pheromone-biosynthesis-activating neuropeptide), showed that the major component, (Z)-13-hexadecen-11-ynyl acetate (1), appears to be the only pheromone compound present in the gland. Comparison of female attractivity with that of the natural extract and synthetic (Z)-13-hexadecen-11-ynyl acetate showed that this chemical is able to elicit a similar activity to that displayed by virgin females in a wind tunnel. In single cell recording experiments, two specialist receptor cell types were found in the trichoid sensilla. One cell type was tuned to enyne acetate 1. The other one was tuned to (Z,Z)-11,13- hexadecadienal and (Z)-13-hexadecen-11-ynal, the major components of the pheromone blend of other Thaumetopoea spp., and constitutes a further example of interspecific inhibitor receptor cells. Our results show that the processionary moth may not need minor components for successful mate recognition.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006406.30444.69
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  • 4
    Electronic Resource
    Electronic Resource
    Behavior of processionary males (Thaumetopoea pityocampa) induced by sex pheromone and analogs in a wind tunnel (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1957-1969 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; processionary moth ; Thaumetopoea pityocampa ; Lepidoptera ; Thaumetopoeidae ; behavior ; wind tunnel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033855
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  • 5
    Electronic Resource
    Electronic Resource
    Initial field trials with the synthetic sex pheromone of the processionary mothThaumetopoea pityocampa (Denis and Schiff.) (1983)
    Springer
    Journal of chemical ecology 9 (1983), S. 85-93 
    Details
    ISSN: 1573-1561
    Keywords: Sex attractant ; sex pheromone ; processionary moth ; Thaumetopoea pityocampa ; Lepidoptera ; Notodontidae ; (Z)-13-hexadecen-11-ynyl acetate ; field test
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Synthetic (Z)-13-hexadecen-11-ynyl acetate has been shown to be highly active in catchingThaumetopoea pityocampa (Denis and Schiff.) males in field trials carried out in different parts of Spain. A variety of formulations containing antioxidants or solid paraffin were tested. Formulations containing 3 and 10% ofE isomer showed a decrease of activity compared with those prepared with pureZ isomer. Dodecyl acetate, also found in the virgin female gland, did not show any synergistic effect when tested in a 9∶1 mixture with the synthetic pheromone. The product exhibited a remarkable persistence of activity under the field conditions even in the absence of stabilizer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987772
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