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  • 1
    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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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Aggregation pheromones of the grain beetle,cryptolestes turcicus (Coleoptera: Cucujidae) (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1071-1081 
    Details
    ISSN: 1573-1561
    Keywords: Cryptolestes turcicus ; Coleoptera ; Cucujidae ; aggregation pheromone ; macrolide ; (Z,Z)-5,8-tetradecadien-13-olide ; (Z)-5-tetradecen-13-olide ; enantiomeric synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two biologically active macrolides were isolated from Porapak Q-captured beetle and frass volatiles ofCryptolestes turcicus (Grouvelle) and identified spectroscopically as (Z,Z)-5,8-tetradecadien-13-olide (I) and (Z)-5-tetradecen-13-olide (II). Natural I was active alone and was synergized by inactive II. The pheromones were male-produced but attractive to both sexes. Pheromone production increased dramatically when insects were aerated on a food source. Pure (R)- and (S)-I were inactive, but mixtures of (R)- and (S)-I were active, the first reported instance of enantiomeric synergism in the Cucujidae.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020676
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  • 4
    Electronic Resource
    Electronic Resource
    Aggregation pheromones of the flat grain beetle,Cryptolestes pusillus (Coleoptera: Cucujidae) (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1053-1070 
    Details
    ISSN: 1573-1561
    Keywords: Cryptolestes pusillus ; coleoptera ; cucujidae ; flat grain beetle ; aggregation pheromone ; macrolide ; (Z)-3-dodecenolide ; (Z)-5-tetradecen-13-olide ; (Z,Z)-3,6-dodecadienolide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Aggregation pheromones were isolated fromCryptolestes pusillus (Schönherr), a coleopteran pest of stored products. Porapak Q-captured beetle and frass volatiles were fractionated by preparative gas-liquid chromatography. The fractions were bioassayed with an arena olfactometer and/or with a two-choice, pitfall olfactometer. Three biologically active, male-produced compounds eliciting aggregation behavior from adultC. pusillus were isolated and identified by spectroscopic methods as (Z)-3-dodecenolide (I), (Z)-5-tetradecen-13-olide (II), and (Z,Z)-3,6-dodecadienolide (III). Compound I was the major volatile produced and was active alone. Compound II was not active alone, but synergized the response to I. Compound III was active alone at higher concentrations, but did not significantly increase the response when added to the most active mixture of I and II, and so it is probably not part of the aggregation pheromone. Pheromone production increased dramatically when the insects were aerated on a food source.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020675
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  • 5
    Electronic Resource
    Electronic Resource
    Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1543-1554 
    Details
    ISSN: 1573-1561
    Keywords: Chiral semiochemicals ; pheromones ; enantiomeric composition ; enantiomeric synergism ; Cryptolestes ferrugineux ; Cryptolestes pusillus ; Cryptolestes turcicus ; Oryzaephilus mercator ; Oryzaephilus surinamensis ; Coleoptera ; Cucujidae ; (Z)-3-dodecen-11-olide ; (Z,Z)-3,6-dodecadien 11-olide ; (Z)-5-tetradecen-13-olide ; (Z,Z)-5,8-tetradecadien-13-olide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012296
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