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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
    (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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  • 4
    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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  • 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
    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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  • 8
    Electronic Resource
    Electronic Resource
    Sex pheromone components of fall cankerworm moth,Alsophila pometaria (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 1579-1596 
    Details
    ISSN: 1573-1561
    Keywords: Alsophila pometaria(Harris) ; fall cankerworm ; Lepidoptera ; Geometridae ; sex pheromone ; (Z,Z,Z,E)-3,6,9,11-nonadecatetraene ; (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene ; (Z,Z,Z)-3,6,9-nonadecatriene ; synthesis ; hydrocarbons
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z,Z,Z,E)-3,6,9,11-Nonadecatetraene and (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene, sex pheromone components ofAlsophila pometaria, were synthesized by stereoselective Wittig reactions and found to be spectroscopically and chromatographically identical to isolated natural material. Flight-tunnel bioassays and field-trapping experiments confirmed that the two tetraenes together with (Z,Z,Z)-3,6,9-nonadecatriene are sex pheromone components. While traps baited with either tetraene individually captured conspecific males in field-trapping experiments, addition of the triene, which captured no males by itself, to either tetraene resulted in synergistic responses.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988426
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  • 9
    Electronic Resource
    Electronic Resource
    Sex attractants for Geometrid and Noctuid moths (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 727-756 
    Details
    ISSN: 1573-1561
    Keywords: Sex attractants ; Lepidoptera ; Geometridae ; Noctuidae ; stereospecific synthesis ; (3Z,6Z,9Z)-triene hydrocarbons ; (3Z,6Z,9S,10R)-9,10-epoxydienes ; (3Z,6Z,9R, 10S)-9,10-epoxydienes ; electroantennogram
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male moths belonging to 17 species of Geometridae and nine species of Noctuidae were captured in traps baited with synthetic chemicals as part of a field screening program. The compounds tested were the C18-C22 homologs of: (1) (3Z,6Z,9Z)-triene hydrocarbons; (2) mixtures containing equal quantities of (3Z,6Z)-cis-9,10-expoxydienes, (3Z,92Z)-cis-6,7-epoxydienes, and (6Z,9Z)-cis-3,4-epoxydienes; (3) (3Z,6Z)-9S,10R-epoxydienes; (4) (3Z,6Z)-9R,10S-epoxydienes; and (5) (3Z,6Z,9Z,11E)-nonadecatetraene. Field captures and electroantennographic assays revealed a high degree of specificity in the responses of many species to the synthetic chemicals. In several species the ability of males to discriminate between the 9S,10R and 9R,10S enantiomers of the monoepoxydiene isomers was clearly shown. Synergists and inhibitors were discovered for several of the reported attractants, some of which were not previously known to have semiochemical activity. The geometrid moths captured includedEpirrhoe sperryi (Herbulot),Mesoleuca ruficillata (Guenée),Triphosa haesitata (Guenée),Metanema inatomaria (Guenée),Prochoerodes transversata (Drury),Cabera erythemaria (Guenée),Synaxis jubararia (Hulst),Dysstroma brunneata ethela (Hulst),Eulithes testata (Linnaeus),Sicya macularia (Harris),Xanthorhoe iduata (Guenée),X. abrasaria aquilonaria (Herrich-Schäffer),X. munitata (Hübner),Itame loricaria (Eversmann),Eupithecia annulata (Hulst),E. rovocastaliata (Packard) andE. satyrata dodata (Taylor). The noctuid moths captured includedBleptina caradrinalis (Guenée),Idia américalis (Guenée),I. aemula (Hübner),Rivula propinqualis (Guenée),Lomanaltes eductalis (Walker),Spargaloma sexpunctata (Grote),Caenurgina distincta (Neumuller),Euclidia cuspidea (Hübner), andZale duplicata (Bethune). Six of the nine noctuid species captured belong to three subfamilies for which sex attractants had not been reported previously. Details for the stereospecific synthesis of (3Z,6Z)-cis-9,10-epoxydienes are also reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988302
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  • 10
    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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