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  • 1
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of agricultural and food chemistry 16 (1968), S. 549-553 
    ISSN: 1520-5118
    Source: ACS Legacy Archives
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Process Engineering, Biotechnology, Nutrition Technology
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  • 2
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Analytical chemistry 44 (1972), S. 1292-1292 
    ISSN: 1520-6882
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
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  • 3
    Electronic Resource
    Electronic Resource
    [s.l.] : Nature Publishing Group
    Nature 239 (1972), S. 109-109 
    ISSN: 1476-4687
    Source: Nature Archives 1869 - 2009
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Notes: [Auszug] Our experience indicates that the standard procedures used for isolation of sex pheromones from extracts of abdominal tips or of whole insects, will not reveal the presence of all sex pheromones. Previously, in two separate studies only one sex pheromone of the codling moth, Laspeyresia pomonella ...
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  • 4
    ISSN: 1570-7458
    Keywords: Lepidoptera ; Tortricidae ; Olethreutinae ; Cydia caryana ; sex pheromone ; electroantennogram ; flight tunnel ; behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Description / Table of Contents: Résumé Les réponses olfactives antennaires de Cydia caryana, mesurées par électroantennogrammes (EAG), aux alcools et acétates à carbones monounsaturés en positions 12 et 14, ont montré que le système conjugué de double liaison, (E)-8-, (E)-10- du dodecadien-1-ol acétate constitue un composé chimique strutural critique de la phéromone sexuelle de C. caryana. De plus, les acétates: (E)-8-dodecen-1-ol,(Z)-8-dodecen-1-ol,(Z)-9-dodecen-1-ol, et le (Z)-12-tetradecen-1-ol, se sont révélés en AEG comme des composés secondaires de la phéromone. L'étude par AEG de la relation dose-réponse a conduit à l'hypothèse de deux catégories de populations de récepteurs de phéromones. L'analyse comportementale des résponses des papillons mâles dans le tunnel de vol aux composés qui ont provoqués les plus forts AEG, on fait estimer que les acétates (E,E)-8,10-dodécadien-1-ol et (Z)-9-dodecen-1-ol ressemblent (ou sont) les constituants de la phéromone sexuelle de C. caryana; tandis que les (Z)-8-dodecen-1-ol et (E)-10-dodecen-1-ol sont, soit des paraphéromones, soit des constituants mineurs de la phéromone. La signification biologique du (Z)-12-tétradécen-1-ol a été difficile à interprêter avec les expériences en tunnel de vol.
    Notes: Abstract Electroantennogram (EAG) measurement of male Cydia caryana moth antennal olfactory response to monounsaturated 12 and 14 carbon alcohols and acetates indicated that the (E)-8-, (E)-10- conjugated double bond system of a dodecadien-1-ol acetate is a critical chemical structural component of the C. caryana sex pheromone. Additionally, EAG measurements implicated (E)-8-dodecen-1-ol acetate, (Z)-8-dodecen-1-ol acetate, (Z)-9-dodecen-1-ol acetate and (Z)-12-tetradecen-1-ol as potential minor pheromonal components. An EAG dosage-response study suggested that there were at least two heterologous populations of pheromone acceptors. Behavioral analysis of male moth response in a flight tunnel to compounds which evoked the stronger EAG responses suggested that (E,E)-8,10-dodecadien-1-ol acetate and (Z)-9-dodecen-1-ol acetate resemble or are C. caryana sex pheromonal components, while (Z)-8-dodecen-1-ol acetate and (E)-10-dodecen-1-ol acetate are either parapheromones or are minor pheromone components. Behavioral significance of (Z)-12-tetradecen-1-ol was difficult to interpret in the flight tunnel.
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 10 (1984), S. 53-61 
    ISSN: 1573-1561
    Keywords: Melissopus latiferreanus ; Lepidoptera ; Tortricidae ; Olethreutinae ; filbertworm ; sex pheromone ; sex attractant ; (E,E)-8 ; 10-dodecadien-1-ol acetate ; (E,Z)-8,10-dodecadien-1-ol acetate ; conjugated diene isomerization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (E,E)- and (E,Z)-8,10-Dodecadien-1-ol acetates were identified in a 1∶4.3 ratio in the extract of abdominal tips of female filbert-worm moths,Melissopus latiferreanus (Walsingham). The identifications were based on electroantennogram (EAG) analysis, gas chromatography, mass spectrometry, ozonolysis, and synthesis. TheE,Z isomer produced the stronger EAG response. In the field tests of various ratios ofE,E∶E,Z, the ratio found in the extract captured the most males. The pureE,E isomer initially was not attractive by itself (〈0.1%E,Z) but became attractive after a few days, presumably because of isomerization. TheE, Z isomer (〈0.1%E,E) was attractive initially, but this compound might have isomerized faster than theE,E isomer. A study of the isomerization showed that regardless of the initial mixture of 8,10-dodecadien-1-ol acetate isomers, almost complete equilibration existed after one month. The equilibrium mixture consisted of 9%Z8,E10, 65%E8,E10, 23%E8,Z10, and 3%Z8,Z10. Concentrations in rubber septa (1∶4 ratio ofE,E toE,Z) of 0.03–3.0 mg/septum produced equivalent trap catches.
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  • 6
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Pyraustinae ; Pyraustini ; Fumibotys fumalis ; sex pheromone ; (E,E)-10 ; 12-tetradecadienyl acetate ; (Z)-11-tetradecenyl acetate ; (E)-11-tetradecenyl acetate ; (Z)-9-tetradecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Compounds identified in sex pheromone gland extracts of femaleFumibotys fumalis (Guenee) consisted of (E,E)-10,12-tetradecadienyi acetate, (Z)-11-tetradecenyl acetate, (E)-11-tetradecenyl acetate, and (Z)-9-tetradecenyl acetate in a ratio of 100:18: 8:4, respectively. The compounds were identified by electroantennographic, gas Chromatographic, mass spectrometric, and chemical derivatization procedures. In mint fields synthetic components in gray elastomeric septa at ratios found in the sex pheromone gland and at doses of 3 or 10 mg of the diene produced trap catch comparable to traps baited with three females.
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  • 7
    ISSN: 1573-1561
    Keywords: Cranberry fruitworm ; Lepidoptera ; Pyralidae ; Acrobasis vaccinii ; sex pheromone ; (E,Z)-8,10-pentadecadien-l-ol acetate ; (E)-9-pentadecen-l-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The following compounds and (approximate ratios) were identified in sex pheromone gland extracts of femaleAcrobasis vaccinii Riley by comparison of gas chromatography-mass spectrometric traces with those of synthetic standards: (E,Z)-, (Z,E)-, (Z,Z), and (E,E)-8, 10-pentadecadien-l-ol acetates (100:1:2:12), a dodecen-l-ol acetate (8), (Z)-8-, (Z)-9-, and (E)-9-pentadecen-l-ol acetates (3:23:4), two heptadecen-l-ol acetates (4:4), tetradecyl, pentadecyl, hexadecyl, and heptadecyl acetates (3:15:10:8), dodecan-l-ol (6), tetradecan-l-ol (5), and hexadecan-l-ol (23). The amount of (E,Z)-8, 10-pentadecadien-l-ol acetate (E8,Z10–15:Ac) in the extract was about 0.5 ng/female. Electroantennographic analysis of gas chromatographic fractions of female sex pheromone gland extract showed that the fraction containingE8,Z10–15:Ac elicited the greatest response. Alone,E8,Z10–15:Ac failed to elicit upwind flight of males in flight-tunnel tests, and traps baited with it did not catch males in field experiments. WhenE8,Z10–15:Ac was combined with (E)-9-pentadecen-l-ol acetate (100:4), male upwind flight response in flight-tunnel tests was equivalent to those obtained with extract of female sex pheromone glands (synthetic, 62%; natural, 51%), but the percent of males flying upwind that contacted the source was lower (synthetic, 47%; natural, 88%). The lower percent of source contact elicited by the synthetic pheromone could be a result of the difference in isomer ratios of 8,10–15:Ac in the natural and synthetic pheromone or could indicate that the synthetic pheromone is incomplete. Traps baited with the 100:4 combination caught large numbers of males in field experiments.
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 9 (1983), S. 1491-1502 
    ISSN: 1573-1561
    Keywords: Insect attractants ; pheromone formulations ; pheromone evaporation rate ; sex pheromones ; Lepidoptera pheromones ; measuring pheromone evaporation ; silanized silica gel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A new method for determining half-lives for the evaporation of sex pheromones from formulations has been developed. A previously unexploited mathematical relationship makes possible the determination of half-lives of over 1000 days by collecting evaporated pheromone for 1–4 hr and measuring the amount collected and the amount left in the formulation. Purified nitrogen flows over the test material and the evaporated pheromone is qualitatively collected on an adsorbent of 80–100 mesh silica gel silanized with octadecyltrichlorosilane. Quantitation is by gas chromatography. Quantitative mass balance was achieved and half-lives determined by this new method are in agreement with half-lives previously determined by measuring the amount of pheromone left in septa after a sequence of time intervals. Previously undetermined half-lives for acetates and alcohols are reported.
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 7 (1981), S. 627-633 
    ISSN: 1573-1561
    Keywords: Insect sex pheromones ; insect sex attractants ; Lepidoptera ; pheromones ; pheromone formulations ; insect population monitoring
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The half-lives (t 1/2) of alcohol sex pheromones, 1-alkanols, acetate sex pheromones, and an epoxide (disparlure) were determined on natural rubber septa. Thet 1/2 values for the homologous alcohols from decanol to heptadecanol increased regularly from 2.2 to 1117 days, but thet 1/2 of octadecanol was 609 days. Thet 1/2 values of (Z)7-, (E)7-, and (Z)9-tetradecen-1-ol acetates were 154, 168, and 199 days, respectively, whereas those of five other tested 14-carbon acetates ranged from 310 to 350 days. The dependence oft 1/2 values on chain length and double-bond position is consistent with the hypothesis that molecular size is an important variable affectingt 1/2 values. Also, in accordance with the hypothesis, when aZ-alkenyl compound has a much shortert 1/2 than the corresponding saturated compound, thet 1/2 values of theZ compound and itsE isomer may be quite different. Thus, (E)-9-tetradecen-l-ol acetate had at 1/2 of 331 days. Thet 1/2 of disparlure was 180 days. The effect of thecis-7,8 epoxide group is apparently similar to that of the olefin group in lowering thet 1/2 below the value that would be expected solely on the basis of chain length.
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 15 (1989), S. 779-790 
    ISSN: 1573-1561
    Keywords: Insect sex pheromones ; controlled release ; formulations ; formulation substrates ; acetates ; n-alkyl acetates ; n-alkenyl acetates ; heat of vaporization ; enthalpy of vaporization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The half-lives (t 1/2) for evaporative loss ofn-alkyl andn-alkenyl acetates from rubber septa were determined at temperatures varying from 15 to 35 °C. The changes int 1/2 with temperature gave high correlations with the equation, Int 1/2 = ΔH/RT+y o where ΔΔH is the heat of vaporization,R is the gas constant,T is the absolute temperature, andy o is a constant. Half-lives changed dramatically with temperature and the degree of change with temperature increased with increasing molecular weight. For mixtures, component ratios changed with temperature, but the degree was modest. At 20 °C there was a 7.5-fold ratio oft 1/2 between members of the homologousn-alkyl orn-alkenyl acetates differing by two carbon atoms. The large change int 1/2 with temperature and with number of carbon atoms is a consequence of the thermodynamic relationships and the temperature range of pheromone usage. Therefore, a similar degree of change inf 1/2 with temperature and number of carbon atoms will apply to other formulations of the same type (those in which the rate of evaporation is first order). The values oft 1/2 at 20 °C mainly agreed very well with those reported previously at room temperature. However, our previously reported values for pentadecyl and hexadecyl acetate were revised. Half-lives were shown to depend on the vapor pressure of a compound in the formulation substrate, but not on the vapor pressure of the pure compound.
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