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  • 1
    Electronic Resource
    Electronic Resource
    [s.l.] : Nature Publishing Group
    Nature 332 (1988), S. 354-356 
    ISSN: 1476-4687
    Source: Nature Archives 1869 - 2009
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Notes: [Auszug] Laying queens were immobilized at -20 °C. Mandibular glands were excised, macerated and extracted twice in HPLC-grade methanol to give a combined total extract of 100 JJL! per queen. A 3-queen equivalent (Qeq) HQMC extract was chromatographed on a micro-column of acid-treated silica gel. The ...
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  • 2
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-1561
    Keywords: Blackheaded fireworm ; Rhopobota naevana (Hubner) ; Rhopobota unipunctana (Haw.) ; Lepidoptera ; Tortricidae ; Olethreutinae ; sex pheromone ; (Z)-11-tetradecenyl acetate ; (Z)-11-tetradecenyl alcohol ; (Z)-9-dodecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Splitless capillary gas chromatography indicated the presence of (Z)- and (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl alcohol in the washes of female abdominal tips of the blackheaded fireworm,Rhopobota naevana (Hubner). Gas chromatography combined with mass spectroscopy confirmed the presence of tetradecenyl acetate in extracts of female tips. The low levels observed in these extracts (〈 1 ng/female equivalent), prevented further chemical and spectroscopic identification. These materials were found to be stimulatory at low levels in electroantennogram studies. A combination of 9 μg of (Z)-11-tetradecenyl acetate and 3 μg of (Z)-11-tetradecenyl alcohol on rubber septa in wing traps provided an effective attractant. (Z)-9-Dodecenyl acetate, a previously reported attractant, did not significantly increase field trapping catches when added to the binary mixture, but was found to enhance trap catches when added to each of the primary components.
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  • 5
    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.
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  • 6
    ISSN: 1573-1561
    Keywords: Oblique-banded leafroller ; Choristoneura rosaceana ; Lepidoptera ; Tortricidae ; sex pheromone ; (Z)-11-tetradecen-1-yl acetate ; (E)-11-tetradecen-1-yl acetate ; (Z)-11-tetradecen-1-ol ; (E)-11-tetradecen-1-ol ; (Z)-11-tetradecenal ; (E)-11-tetradecenal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z)-11-Tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol were previously reported as the sex pheromone in New York strains of the oblique-banded leafroller,Choristoneura rosaceana (Harris), and (E)-11-tetradecen-1-ol was tentatively identified in female tip extracts. For Okanagan Valley strains ofC. rosaceana, an additional component, (Z)-11-tetradecenal, was identified from female tip extracts by split-less capillary gas-liquid chromatography and mass spectroscopy and was strongly stimulatory in electroantennogram studies. In field tests, 3 mg of 96.5∶2∶1.5 (Z)-11-tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol (containing approx. 1%E isomer) was not as attractive as female-baited traps, and significant numbers of European leafrollerArchips rosanus L. were attracted. The above blend with 1% (Z)-11-tetradecenal added was significantly more attractive than traps baited with femaleC. rosaceana, butA. rosanus males were still attracted. Increased percentages of (Z)-11-tetradecenal up to 4% caused increased catches ofC. rosaceana and decreased catches ofA. rosanus. Low amounts of (E)-11-tetradecen-1-ol and (E)-11-tetradecenal male also contribute to increased specificity of the synthetic pheromone blend toC. rosaceana.
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 16 (1990), S. 851-860 
    ISSN: 1573-1561
    Keywords: Hymenoptera ; Apidae ; Apis mellifera L. ; honeybee queen mandibular semiochemicals ; retinue pheromone ; splitless capillary gas chromatography ; (E)-9-keto-2-decenoic acid ; methylp-hydroxybenzoate ; 4-hydroxy-3-methoxyphenylethanol ; (R,E)-(−)- and (S,E)-(+)-9-hydroxy-2-decenoic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The ontogeny of the five queen mandibular gland semiochemicals that initiate and maintain the retinue behavior of worker honeybees was investigated by quantitative splitless capillary gas chromatography. No detectable pheromone is present at the time of eclosion, but decenoic acid levels build up rapidly during the first week of the queen's life. Two aromatic components attain detectable levels later, with the more plentiful methylp-hydroxybenzoate preceding the 4-hydroxy-3-methoxyphenylethanol. Pheromone levels are maximal in mature, mated, laying queens. The ratio of (R,E)-(−)-9-hydroxy-2-decenoic acid to the (S,E)-(+) enantiomer increases with the age of the queen. Pheromone levels in queen mandibular glands are largely unaffected by queen banking, restraint with workers in mailing cages, and limited storage on dry ice. All major body parts of typical queens, especially the head and legs, have sufficient mandibular exudate to be highly attractive to worker bees.
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 17 (1991), S. 1517-1527 
    ISSN: 1573-1561
    Keywords: Pheromone ; ipsenol ; cis-verbenol ; chirality ; Ips latidens ; Coleoptera ; Scolytidae ; predator ; kairomone ; Enoclerus sphegeus ; Thanasimus undatulus ; Cleridae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Ipsenol was identified from the frass of male, but not female,Ips latidens from British Columbia, feeding in phloem tissue of lodgepole pine,Pinus contorta var.latifolia. The responses ofJ. latidens to sources of ips-enol andcis-verbenol were determined with multiple-funnel traps in stands of lodgepole pine in British Columbia. Ipsenol attracted both male and femaleI. latidens, verifying that it is a pheromone for this species. MaleI. latidens showed a slight preference for (S)-(−)-ipsenol.cis-Verbenol was not produced by beetles of either sex and, in contrast to an earlier report, both enantiomers inhibited attraction to ipsenol-baited traps. The predators,Enoclerus sphegeus andThanasimus undatulus (Cleridae), were attracted to traps baited withcis-verbenol and ipsenol.
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 24 (1998), S. 1049-1075 
    ISSN: 1573-1561
    Keywords: Semiochemicals ; primary attraction ; kairomones ; Scolytus ventralis ; Thanasimus undatulus ; Abies grandis ; monoterpenes ; sesquiterpenes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In laboratory bioassays, Porapak Q-captured and steam-distilled volatiles from the bark of host trees, Abies grandis, particularly from root-rot-infected trees, attracted 50–70% of male and female fir engravers, Scolytus ventralis. Gas chromatographic–electroantennographic detection (GC-EAD) analyses of Porapak Q-captured bark volatiles revealed 19 EAD-active compounds of which 13 (mostly monoterpenes) were identified by GC–mass spectrometry (GC-MS). In separate field experiments, multiple-funnel traps baited with two blends of these 13 synthetic volatiles released at 280 and 340 mg/ 24 hr attracted 66 and 93% of the total S. ventralis captured, respectively. The clerid predator, Thanasimus undulatus, also responded strongly to the kairomonal volatiles. Additional experiments produced no evidence for aggregation pheromones in S. ventralis. These included laboratory bioassays and GC and GC-EAD analyses of Porapak Q-captured volatiles from male- and female-infested logs or trees undergoing mass attack in the field, GC analyses and/or bioassays of extracts from female accessory glands, extracted volatiles from emerged, attacking and juvenile hormone-treated beetles of both sexes, and videotape analysis of the behavior of attacking beetles on the bark surface. We argue against the hypothesis of pheromone-mediated secondary attraction in S. ventralis and conclude that the attack dynamics of this species can be explained solely by its sensitive primary attraction response to host volatiles.
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  • 10
    ISSN: 1573-1561
    Keywords: Chiral semiochemicals ; pheromones ; enantiomeric composition ; Ips pini ; Coleoptera ; Scolytidae ; Apis mellifera ; Hymenoptera ; apidae ; Cryptolestes Ferrugineus ; Cucujidae ; acetyl lactate diastereoisomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A method is described for determining the enantiomeric composition of chiral alcohols, lactones, and hydroxy acids in quantities ranging from 25 ng to 10 μg. Derivatization of the substance with chirally pure acetyl lactate, followed by splitless capillary gas chromatography, enables enantiomeric determinations to be made within 1–3% of the actual value. This technique was applied in the determination of semiochemical inIps pini (Say),Apis mellifera (L.), andCryptolestes ferrugineus (Stephens). The results indicate that considerable variability exists within populations of some insects in the composition of their chiral semiochemicals, whereas others produce substances of constant composition.
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