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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
    Sex attractants and sex pheromone components of noctuid mothsEuclidea cuspidea,Caenurgina distincta, and geometrid mothEupithecia annulata (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 2095-2111 
    Details
    ISSN: 1573-1561
    Keywords: Pheromone ; sex attractant ; Noctuidae ; Geometridae ; epoxide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pheromone components and sex attractant blends consisting of 3Z,6Z,9Z-triene hydrocarbons and racemic and chiral forms of3Z,6Z-cis-9, 10-epoxydienes have been elucidated for two noctuid and one geometrid moth species. MaleEuclidea cuspidea moths were attracted to blends of 3Z,6Z,9Z-heneicosatriene (3Z,6Z,9Z-21∶H) with 3Z,6Z-cis-9,10-epoxyheneicosadiene (3Z,6Z-cis-9,10-epoxy-21∶H). In addition to these compounds, 3Z,6Z,9Z-20∶H, and two regioisomeric C21 epoxides were tentatively identified in pheromone gland extracts.Caenurgina distincta moths were attracted by an 8∶∶1 blend of 3Z,6Z,9Z-20∶H with3Z,6Z-cis- 9,10-epoxy-20∶H.Eupithecia annulata moths were attracted by either 3Z,6Z-cis-9,10-epoxy-20∶H or 3Z,6Z-cis-9,10-epoxy-21∶H, and by the 95,10R enantiomer of each epoxide. 3Z,6Z,9Z-21∶H and 3Z,6Z-cis-9,10-epoxy-21∶H were tentatively identified from pheromone glands. Pheromone components were identified by a combination of coupled gas chromatography-electroantennography, gas chromatography-mass spectrometry, and field bioassays.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987994
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    3Z,6Z,9Z-Trienes and unsaturated epoxides as sex attractants for geometrid moths (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 2307-2316 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; sex attractant ; behavioral antagonist ; 6Z,9Z-cis-3,4-epoxy-nonadecadiene ; 3Z,9Z-cis-6,7-epoxy-nonadecadiene ; 3Z,6Z,9Z-heptadecatriene ; 3Z,6Z,9Z-nonadecatriene ; Probole amicaria ; Sicya macularia ; Lomographa semiclarata
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sex attractants for three species of geometrid moths were discovered during field screening of 3Z,6Z,9Z-trienes, and the racemic monoepoxydienes derived therefrom. MaleProbole amicaria moths were attracted to lure blends containing 6Z,9Z-cis-3,4-epoxy-nonadecadiene (6Z,9Z-cis-3,4-epoxy-19∶H) with 3Z,9Z-cis-6,7-epoxy-19∶H. 3Z,6Z,9Z-19∶H was positively identified and 6Z,9Z-cis-3,4-epoxy-19∶H was tentatively identified in extracts of female pheromone glands by coupled gas chromatography-electroantennogram detection (GC-EAD) and gas chromatography-mass spectrometry (GC-MS).Sicya macularia male moths were attracted by blends of 3Z,6Z,9Z-19∶H and 6Z,9Z-cis-3,4-epoxy-19∶H. The attractive response was strongly antagonized by small amounts of 3Z,9Z-cis-6,7-epoxy-19∶H, or by larger amounts of 3Z,6Z-cis-9,10-epoxy-19∶H.Lomographa semiclarata male moths were attracted by a variety of lures containing 3Z,6Z,9Z-17∶H as a major component. 3Z,6Z,9Z-17∶H was tentatively identified in a female pheromone gland extract by GC-EAD.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01026940
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    Paper (German National Licenses)
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