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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
    (3Z,6Z,9Z)-Nonadecatriene and enantiomers of (3Z,9Z)-cis-6,7-Epoxy-nonadecadiene as sex attractants for two geometrid and one noctuid moth species (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 2153-2166 
    Details
    ISSN: 1573-1561
    Keywords: Attractant ; Geometridae ; Noctuidae ; Eufidonia convergaria ; Caripeta angustiorata ; Rivula propinqualis ; (3Z,6Z,9Z)-nonadecatriene ; (3Z,9Z)-(6R,7S)-epoxy-nonadecadiene ; (3Z,9Z)-(6S,7R)-epoxy-nonadecadiene ; (3Z,9Z)-cis-6,7-epoxy-nonadecadiene ; Lepidoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sex attractants for the geometrid mothsEufidonia convergaria andCaripeta angustiorata, and the noctuid mothRivula propinqualis have been elucidated during field screening of a series of (3Z,6Z,9Z)-triene hydrocarbons (C17–22), and the racemic and enantiomerically enriched monoepoxydienes derived from those hydrocarbons. Biologically active compounds were identified by a combination of field testing of synthetic standards, electroantennography, and coupled gas chromatography-electroantennogram detection.E. convergaria males were optimally attracted by a 1∶1 blend of (3Z,9Z)-(6S,7R)-epoxy-nonadecadiene (3Z,9Z-6S,7R-epoxy-19∶H); other abbreviations follow the same system) with (3Z,6Z,9Z)-nonadecatriene (3Z,6Z,9Z-19∶H). The 6R,7S enantiomer of the epoxide had no apparent biological activity, either as an attractant or as a behavioral antagonist. Male moths also were attracted to blends of the C18 and C20 homologs of the triene and the epoxide. 3Z,6Z,9Z-19∶H and 3Z,6Z-cis-6,7-epoxy-19∶H were identified inE. convergaria female pheromone gland extracts. Males of the geometrid moth speciesC. angustiorata were attracted by a 1∶1 blend of 3Z,6Z,9Z-19∶H and enantiomerically enriched 3Z,9Z-6R,7S-epoxy-19∶H. Males of the noctuid mothR. propinqualis were attracted by an approximately 10∶1 blend of 3Z,6Z,9Z-19∶H and enantiomerically enriched 3Z,9Z-6S, 7R-epoxy-19∶H. The components were synergistic, with neither being attractive alone. The blend ratio was quite specific, as the attractiveness of blends decreased sharply on either side of the optimum ratio.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01026927
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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
    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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  • 5
    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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  • 6
    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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  • 7
    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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  • 8
    Electronic Resource
    Electronic Resource
    Identification and bioassay of sex pheromone components of carob moth,Ectomyelois ceratoniae (Zeller) (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 1973-1988 
    Details
    ISSN: 1573-1561
    Keywords: Flight tunnel ; gas chromatography-electrophysiology ; mass ; spectrometry ; aldehydes ; (Z,E)-9,11,13-tetradecatrienal ; (Z,E)-9,11-tetra-decadienal ; (Z)-9-tetradecenal ; pheromone ; Lepidoptera ; Pyralidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three sex pheromone components of the carob moth were isolated and identified from the extract of female pheromone glands, using a variety of techniques including coupled gas chromatographic-electroantennographic recordings, coupled gas chromatographic-mass spectrometric analysis, microozonolysis, electroantennographic assays of monounsaturated standards, wind-tunnel bioassays, and field trials. The major component was identified as (Z,E)-9,11,13-tetradecatrienal, a novel lepidopterous pheromone component structure. Two minor components, either one of which improves the upwind flight response of males when blended with the major component, were identified as (Z,E)-9,11-tetradecadienal, and (Z)-9-tetra-decenal.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00992582
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  • 9
    Electronic Resource
    Electronic Resource
    Effects of host plant,Gossypium hirsutum L., on sexual attraction of cabbage looper moths,Trichoplusia ni (Hübner) (Lepidoptera: Noctuidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2959-2974 
    Details
    ISSN: 1573-1561
    Keywords: Cabbage looper ; Trichoplusia ni ; Lepidoptera ; Noctuidae ; pheromone ; kairomone ; attractants ; host finding ; (S)-(+)-linalool
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Unmated female or male cabbage looper moths,Trichoplusia ni (Hübner), were attracted more often in a flight tunnel to a cage with moths of the opposite sex and a bouquet of cotton foliage. Increased sexual attractiveness of females with plants may be a result of stimulation of pheromone release in response to plant odor, since more males were attracted when odor of cotton foliage was passed over females than when odor of females was passed over cotton foliage before venting into the flight tunnel. Increased sexual attractiveness of males with plants is due in part to host odor enhancement of female attraction to male pheromone, since more females were attracted to synthetic male pheromone (a blend of enantiomers of linalool and isomers of cresol) and a cotton leaf extract than were attracted to male pheromone alone. A short synthesis procedure was developed for (S)-(+)-linalool, the major component of the male sex pheromone, isolated from hair pencils, used in these tests.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02098402
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  • 10
    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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