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  • Geometridae  (6)
  • (3S,4R)-3-methyl-octan-4-ol  (1)
  • 2000-2004
  • 1990-1994  (7)
  • 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
    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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  • 6
    Electronic Resource
    Electronic Resource
    Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2653-2671 
    Details
    ISSN: 1573-1561
    Keywords: Coleoptera ; Curculionidae ; Rhynchophorus phoenicis ; Rhynchophorus cruentatus ; aggregation pheromone ; pheromone chirality ; (3S,4S)-3-methyl-octan-4-ol ; (3R,4R)-3-methyl-octan-4-ol ; (3S,4R)-3-methyl-octan-4-ol ; (3R,4S)-3-methyl-octan-4-ol ; (4S,5S)-5-methyl-octan-4-ol ; (4R,5R)-5-methyl-octan-4-ol ; (4S,5R)-5-methyl-octan-4-ol ; (4R,5S)-5-methyl-octan-4-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil,Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by maleR. phoenicis and maleR. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, withR. phoenicis in Côte d'Ivoire andR. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02036199
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  • 7
    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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