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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and field testing of enantiomers of 6Z,9Z-cis-3,4-epoxydienes as sex attractants for geometrid moths (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 2317-2339 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; sex pheromone ; sex attractant ; behavioral antagonist ; enantiomer ; (6Z,9Z,3S,4R)-epoxy-heptadecadiene ; (6Z,9Z,3R,4S)-epoxy-heptadecadiene ; (3Z,9Z,6S,7R)-epoxyheptadecadiene ; (6Z,9Z,3S,4R)-epoxy-nonadecadiene ; (6Z,9Z,3R,4S)-epoxy-nonadecadiene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Stereoselective syntheses of chiral C17 to C21 6Z,9Z-cis-3,4-epoxydienes were developed. Field tests of the enantiomerically enriched epoxides as components of synthetic sex attractant lures were carried out, and those with C17 and C19 chain lengths, particularly, were attractive to male moths of several species. Moths were usually specifically attracted by one of a pair of enantiomers, and the opposite enantiomer could actually be a behavioral antagonist. Males belonging to nine species of Geometridae were captured.Probole amicaria (Herrich-Schäffer) males were taken in traps baited with the mixture (6Z,9Z,3S,4R)-epoxy-nonadecadiene (6Z,9Z,3S,4R-epoxy-19∶H) + 3Z,9Z,6R,7S-epoxy-19∶H + 3Z,6Z,9Z-19∶H(9∶1∶8). Other species responding to the C19 compounds included (attractant components follow in parentheses);Sicya macularia (Harris) (6Z,9Z,3S,4R-epoxy-19∶H + 3Z,6Z,9Z-19∶H),Anavitrinella pampinaria (Guenée) (6Z,9Z-cis-3,4-epoxy-19∶H + 3Z,9Z,6S,7R-epoxy-19∶H), andLycia ursaria (Walker) (6Z,9Z-3S, 4R-epoxy-19∶H + 3Z,6Z,9Z-19∶H). Males of the following species were captured byC 17 epoxides:Itame occiduaria (Packard) (6Z,9Z,3R,4S-epoxy-17∶H + 3Z,6Z,9Z-17∶H),Itame brunneata (Thunberg) (6Z,9Z,3S,4R-epoxy-17∶H),Epelis truncataria (Walker) (both enantiomers of 6Z,9Z-cis-3,4-epoxy-17∶H),Semiothisa ulsterata (Pearsall) (3Z,9Z-6S,7R-epoxy-17∶H), andS. signaria dispuncta (Walker) (3Z,9Z-cis-6,7-epoxy-17∶H + 3Z,6Z,9Z-17∶H). The interactions among enantiomers and regioisomers are discussed as a mechanism by which cross attraction between sympatric species is limited.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01026941
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  • 2
    Electronic Resource
    Electronic Resource
    Behavioral and electrophysiological activity of (Z,E)-7,9,11-dodecatrienyl formate, a mimic of the major sex pheromone component of carob moth,Ectomyelois ceratoniae (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 2331-2352 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; sex pheromone ; (Z,E)-9,11,13-tetradecatrienal ; mimic ; (Z,E)-7,9,11-dodecatrienyl formate ; wind tunnel ; attractant ; electrophysiology ; receptor cell
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The behavioral and electrophysiological activity of a mimic [(Z,E)7,9,11-dodecatrienyl formate] of the major sex pheromone component [(Z,E) 9,11,13-tetradecatrienal] of carob moth was assessed. Wind-tunnel bioassays demonstrated that the formate was as effective as natural gland extracts, and significantly more effective than the trienal alone or than the trienal blended with two minor pheromone components, in evoking source contact. Dispensers containing the formate were as effective as trienal-containing blend lures in attracting males when placed at the same dosage in traps in date gardens. Single-cell recordings showed that at least two olfactory neurons, differentiated by spike amplitude, are located in the long trichoid hairs on male carob moth antennae. Dose-response relationships indicated that puffs from cartridges loaded with at least 0.1 μg of the formate or of the trienal were necessary to elicit spiking by either the small or the large-spiking cell within a sensillum. Cross-adaptation studies demonstrated that both compounds stimulated the same large-spiking cell. The frequencies of spikes evoked from the large cell when stimulated by emissions from 0.1-μg, 1-μg, or 10-μg cartridges of either the formate or the trienal were not significantly different, suggesting that the formate is an effective mimic of the trienal at the antennal receptor cell level.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984953
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  • 3
    Electronic Resource
    Electronic Resource
    Use of a sex attractant and an inhibitor for monitoring winter moth and bruce spanworm populations (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1319-1330 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Operophtera bruceata (Hulst) ; Bruce spanworm ; Operophetra brumata L. ; winter moth ; sex pheromone ; (Z,Z,Z)-1,3,6,9-nonadecatetraene ; inhibitor ; (E,Z,Z)-1,3,6,9-nonadecatetraene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A single sex pherormone component was isolated from abdominal tip extracts of female Bruce spanworm.Operophtera bruceata (Hulst). This was identified as (Z,Z,Z)-1,3,6,9-nonadecatetraene by capillary gas chromatography (GC), electroantennography, and mass spectrometry. In addition, hexane extracts of female abdominal tips from Bruce spanworm and the winter moth.O. brumata L., were analyzed by GC coupled to an electroantennographic detector (GC-EAD). The extracts ofO. bruceata andO. brumata females elicited only a single response, at the same retention time, from antennae of their conspecific and reciprocal males. In field tests conducted in Saskatchewan, traps baited with the synthetic tetraene captured Bruce spanworm males. In tests carried out on Vancouver Island, British Columbia, where the two species coexist, both Bruce spanworm and winter moth males were captured. The attractancy of lures containing the synthetic pheromone alone and in combination with several structurally related analogs was field tested at both locations. One of these, an isomer of the natural pheromone, (E,Z,Z)-1,3,6,9-nonadecatetraene, inhibited the capture of Bruce spanworm males but had no effect upon the number of winter moth males which were taken. Thus, populations of these two very similar species can be distinguished by employing traps baited with pheromone ± the inhibitor. Coneorifice Hara traps were found useful for field trapping males of both species.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012279
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  • 4
    Electronic Resource
    Electronic Resource
    Sex pheromone components of three species ofSemiothisa (Geometridae), (Z,Z,Z)-3,6,9-heptadecatriene and two monoepoxydiene analogs (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1371-1383 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Semiothisa signaria dispuncta ; Semiothisa bicolorata ; Semiothisa ulsterata ; Semiothisa delectata ; Semiothisa neptaria ; (Z,Z,Z)-3,6,9-heptadecatriene ; (Z,Z)-6,9-cis-3,4-epoxy-heptadecadiene ; (Z,Z)-3,9-cis-6,7-epoxy-heptadecadiene ; sex attractant ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Adult males ofSemiothisa signaria dispuncta (Walker) were attracted to field traps baited with (Z,Z,Z)-3,6,9-octadecatriene and (Z,Z)-6,9-cis-3,4-epoxy-octadecadiene. However, analyses of sex pheromone gland extracts of females of this species by GC-MS and by GC in combination with an electroantennograph detector (GC-EAD) showed the pheromone to be comprised of a mixture of the next lower homologs: (Z,Z,Z)-3,6,9-heptadecatriene and (Z,Z)-6,9-cis-3,4-epoxy-heptadecadiene. Blends of these two C17 compounds were subsequently found to be more attractive to males in the field than the corresponding C18 mixtures. Sex pheromones of two otherSemiothisa species were also found to contain C17 components. (Z,Z,Z)-3,6,9-Heptadecatriene, detected by GC-EAD analysis of a female abdominal tip extract ofS. bicolorata (Fabricius), attracted conspecific males, and this attraction was significantly reduced by additions of (Z,Z)-6,9-cis-3,4-epoxyheptadecadiene, the major pheromone component ofS. signaria dispuncta, to the lure. (Z,Z)-3,9-cis-6,7-Epoxy-heptadecadiene was detected by GC-EAD analysis as the primary male antennal stimulatory component present in abdominal tip extracts ofS. ulsterata (Pearsall), and males of this species were attracted to traps baited with this epoxide. Each of these three C17 compounds constitute previously unknown lepidopteran sex pheromone components. Blends of (Z,Z, Z)-3,6,9-heptadecatriene and (Z,Z)-3,9-cis-6,7-epoxyheptadecadiene attracted males of a fourth species,S. delectata Hulst, but no females of this species were obtained to permit analysis of its sex pheromone. The occurrence of (Z,Z,Z)-3,6,9-heptadecatriene inS. neptaria (Guenee) females was indicated by GC-MS analysis of an abdominal tip extract; however, no males were attracted to any of the fielded mixtures containing this hydrocarbon.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012284
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