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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
    Identification and field testing of female-produced sex pheromone components of the spring cankerworm,Paleacrita vernata Peck (Lepidoptera: Geometridae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 3393-3409 
    Details
    ISSN: 1573-1561
    Keywords: Pheromone ; attractant ; 6(Z),9(Z)-nonadecadiene ; 3(Z),6(Z),9(Z)-nonadecatriene ; 3(Z),6(Z),9(Z)-eicosatriene ; 6(Z),9(Z)-cis-3 ; 4-epoxynonadecadiene ; Paleacrita vernata ; spring cankerworm ; Lepidoptera ; Geometridae ; trap height ; behavioral antagonist
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two sex pheromone components, 3(Z),6(Z),9(Z)-nonadecatriene (3Z,6Z,9Z-19 ∶ H), and 3(Z),6(Z),9(Z)-eicosatriene (3Z,6Z,9Z-20∶ H), have been positively identified, and a third component, 6(Z),9(Z)-nonadecadiene (6(Z),9(Z)-19 ∶ H) has been tentatively identified from abdominal tip extracts of female spring cankerworm moths,Paleacrita vernata Peck (Lepidoptera∶ Geometridae). The pheromone components were identified by a combination of gas chromatography, electroantennography, mass spectrometry, chemical tests, comparison with standards, and field testing. Only 3Z,6Z,9Z-20 ∶ H exhibited significant attractant activity when tested alone, and it was potentiated by the other two components. The attractive blend was an 8∶2∶1 ratio of 3Z,6Z,9Z-20∶H/3Z,6Z,9Z-19∶H/6Z,9Z-19∶H. However, the two-component blend of 3Z,6Z,9Z-20 ∶ H and 6Z,9Z-19 ∶ H (8∶1 ratio) was as attractive as the three-component blend in further field tests. A series of related compounds, the diene monoepoxides available from epoxidation of C19 and C20 3Z,6Z,9Z-trienes, some of which have been found in the pheromone blends of other moth species, were tested as behavioral antagonists. The attraction of male moths to synthetic lures was suppressed by the addition of 6Z,9Z-cis-3,4-epoxy-nonadecadiene to the lures. Additional experiments were performed to determine the effects of lure dosage, trap height, and trap design on the numbers of male moths captured.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982106
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  • 4
    Electronic Resource
    Electronic Resource
    Geometrical and positional isomerization of alkenyl acetates produced by hydrogenation of alkynyl acetates over palladium metal catalysts (1978)
    Springer
    Journal of chemical ecology 4 (1978), S. 657-663 
    Details
    ISSN: 1573-1561
    Keywords: Pheromone ; trans isomer ; cis isomer ; alkenyl acetate ; alkynyl acetate ; hydrogenation ; isomerization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Alkenyl acetates containing both geometrical isomers can be produced by a single controlled catalytic hydrogenation of the corresponding alkynyl acetate. The hydrogenation is capable of yielding formulations containing up to 60% trans isomer; the reduction is attended by positional isomerization in both geometrical isomers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00990276
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 911-929 
    Details
    ISSN: 1573-1561
    Keywords: Sex attractant ; pheromone ; enantiomer ; Lepidoptera ; Noctuidae ; Geometridae ; Euchlaena madusaria ; Xanthotype sospeta ; Palthis angulalis ; Anacamptodes humaria ; (Z,Z)-6,9-nonadecadiene ; (Z)- 6- cis- 9,10-epoxynonadecene ; (Z)-9-cis-6,7-epoxynonadecene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Enantiomerically enriched forms of (Z)-6-cis-9,10-epoxymonoenes and (Z)-9-cis-6,7-epoxymonoenes of chain lengths C17−20 were synthesized by Sharpless asymmetric epoxidation of allylic alcohol intermediates, followed by tosylation or halogenation and chain extension. The resulting monounsaturated epoxides were field tested as sex attractants for lepidopteran species.Euchlaena madusaria Walker males were attracted to blends of the enantiomers of (Z)-6- cis- 9,10-epoxynonadecene 6Z-cis-9,10-epoxy-19:H; IUPAC name [2α,3α(Z)]-2-pentyl-3-(2-dodecenyI)oxirane in combination with 6Z,9Z-19: H. The response was antagonized by 9Z-cis-6,7-epoxy-19: H. 6Z,9Z-19: H was tentatively identified in pheromone gland extracts.Xanthotype sospeta Drury male moths were attracted to lures containing 6Z-9S,10R-epoxy-19: H; the response was antagonized by the opposite enantiomer.Pal-this angulalis Hübner males were attracted to 9Z-6S,7R-epoxy-19:H; the opposite enantiomer was antagonistic. 6Z,9Z-19:H and 9Z-cis-6,7-epoxy-19:H and 9Z-cis-6,7-epoxy-19:H were tentatively identified in pheromone gland extracts fromAnacamptodes humaria Guenée females. In field trails, 9Z-6R,7S-epoxy-19:H proved to be the attractive enantiomer, and the response was potentiated by 6Z,9Z-19:H. Mechanisms by which unique chemical communication channels are maintained by each species are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01395599
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