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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 15 (1989), S. 601-617 
    ISSN: 1573-1561
    Keywords: Ostrinia nubilalis ; Lepidoptera ; Pyralidae ; redbanded leafroller ; Argyrotaenia velutinana ; Tortricidae ; pheromone analogs ; sex stimulation ; bioassay ; flight-tunnel behavior ; field bioassay ; molecular mechanics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The biological activity of analogs of the pheromone components of the European corn borer,Ostrinia nubilalis, (Z)- and (E)-11-tetradecen1-ol acetate, in which modifications were made in the terminal alkyl portion were studied in the three pheromonal types of the insect. European corn borer males respond to pheromonal stimuli at three levels of behavioral activity, i.e., short-range sexual stimulation, activation in the flight tunnel, and response in the field. Structural requirements for elicitation of response at these levels were found to be increasingly restrictive, respectively. Flighttunnel activity was induced only by compounds that had a total chain length of 13 or 14 carbons and in which branching at carbon 13 was limited to one methyl group or a cyclopropyl group. Three new analogs were active in the flight tunnel, viz., (E and (Z)-13-methyl-11-tetradecen-1-ol acetate and (Z)-12-cyclopropyl-11-dodecen-1-ol acetate. The cyclopropyl analog was the most active analog against theZZ type of the European corn borer. TheE isomer, however, was pheromonally inactive in theEE type and was shown to be a pheromone antagonist. This dissimilarity is most likely due to differences in structure of the receptors in the European corn borer strains. Analogs that were biologically active against the European corn borer were tested against the redbanded leafroller,Argyrotaenia velutinana, which also uses (Z)- and (E)-11-tetradecen-1-ol acetate as part of its pheromone. Results showed that the redbanded leafroller pheromone acceptor system is different from that of the European com borer; marginal behavioral response was elicited by only one of the new analogs. Thus, although both species use 11-tetradecen-1-ol acetate isomers as their pheromone, the mechanisms by which they are perceived are different.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 18 (1992), S. 283-298 
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Ostrinia nubilalis ; European corn borer ; tritiated pheromone ; 11-tetradecenyl acetate ; sensory biochemistry ; catabolism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Isomers of [11,12-3H2]-11-tetradecenyl acetate (57 Ci/mM) were synthesized. Behavioral assay of the two compounds using Z- and E-type European corn borer (ECB) males showed that introduction of tritons into the double bond of the pheromone caused a significant isotope effect in the E-type ECB but not in the Z-type ECB. Measurements of tritium associated with the male antennae after a 3-min exposure showed that radioactivity equivalent to 10−7 mol pheromone was adsorbed onto male antennae. Time-course in vivo metabolic studies with picogram amounts of compound applied topically to antennae of E- and Z-type males and Z-type females showed that they metabolized pheromone similarly but females degraded pheromone more slowly than males. Pheromone was hydrolyzed, and the only other major radiolabeled metabolite observed by combined high-pressure liquid chromatography-radiodetection was tritiated water. Capillary gas chromatography and radiomonitoring permitted detection of a trace amount of 11-tetradecenoic acid, which indicated alcohol oxidase activity is associated with the antennae. Evidence shows that clearing of pheromone from the ECB male antennae involves hydrolysis and oxidation of the alcohol to fatty acid, which in turn is degraded, probably via β-oxidation, to carbon dioxide and water.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1573-1561
    Keywords: stable fly ; Stomoxys calcitrans (L.) ; pheromone ; sex pheromone ; branched alkanes ; mating stimulant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Each of 20 methyl-branched and 1,5-dimethyl-branched alkanes that comprise the active principle of saturated hydrocarbons of the female stable fly,Stomoxys calcitrans (L.), was synthesized and evaluated for mating stimulant activity. The compounds that showed the highest degree of activity in bioassays were 15-methyl- and 15,19-dimethyltritriacontanes.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-1561
    Keywords: Fannia canicularis (L.) ; little house fly ; pheromone ; sex pheromone ; (Z)-9-pentacosene ; heneicosan-8-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chromatograms of the cuticular lipids washed from recently emerged female and maleFannia canicularis (L.) flies were nearly identical, but by the time the flies were 5 days old, the cuticular components of the two sexes differed considerably. A monoolefin which constituted 66% of the cuticular lipid from 5-day-old females stimulated a copulatory response from males and was identified as (Z)-9-pentacosene. The cuticular lipid of the same age males contained only 1% of this compound. Although all the major constituents of the cuticular lipid from mature females were hydrocarbons, 27% of the lipid washed from 5-day-old males was a nonhydrocarbon material that was represented by a single GLC peak. This material was identified as heneicosan-8-ol acetate.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 5 (1979), S. 353-361 
    ISSN: 1573-1561
    Keywords: Stable fly ; Stomoxys calcitrans (L) ; pheromone ; mating stimulants ; alkenes ; cuticular lipids ; copulatory behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cuticular alkenes of the female stable fly,Stomoxys calcitrans (L), which were responsible for inducing male fly copulatory behavior are (Z)-9-hentriacontene, (Z)-9-tritriacontene, 13-methyl-1-hen-triacontene and 13-methyl-1-tritriacontene. The identifications of the branched alkenes and the synthesis of these four compounds are described. Bioassays indicate that these materials in combination with previously described methyl branched alkanes are more active than the individual components.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 3 (1977), S. 251-255 
    ISSN: 1573-1561
    Keywords: stable fly ; Stomoxys calcitrans (L.) ; pheromone ; sex pheromone ; polyene ; mating stimulant ; (Z,Z)-1,7,-13-pentacosatriene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The major component of the cuticular lipids of male stable flies,Stomoxys calcitrans (L.), was identified as (Z,Z)-1,7,13-pentacosatriene. The identification was confirmed by synthesis. This material is of unknown biological function; it is apparently not produced by female stable flies.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 16 (1990), S. 1591-1604 
    ISSN: 1573-1561
    Keywords: Ostrinia nubilalis ; Lepidoptera ; Pyralidae ; European corn borer ; (E)- and (Z)-11-tetradecen-1-ol acetate ; pheromone analogs ; insect behavior ; sex pheromone ; inhibition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The male sexual behavior-stimulating and inhibiting properties of a series of analogs of the European corn borer sex pheromone were determined in a flight tunnel. The structural requirements for inhibition of pheromonal response were far less restrictive than those for elicitation of that response. Analogs that by themselves elicited upwind flight response from males at a low dose were generally less inhibitory to male response than many of the analogs that had no pheromonal activity. These findings suggest that many pheromone analogs bind to pheromone receptors without provoking behavioral response and possibly undergo slower degradation on the antenna than pheromonally active compounds. The disparity of response to analogs by two pheromonal types of the European corn borer indicates that the pheromone receptor and pheromone catabolic systems are biochemically very different in the two types.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 1573-1561
    Keywords: Fannia femoralis (Stein) ; pheromone ; mating stimulant pheromone ; (Z)-11-hentriacontene ; cuticular lipid ; fly
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cuticular lipids of male and femaleFannia femoralis were similar for recently emerged insects but soon began to develop chromatographic patterns characteristic of each sex. Mature females contained more C31 and C33 monoolefin in the cuticular lipid than males. Also, the double bonds in the monoolefins of the female lipid were situated predominantly at the eleventh and thirteenth carbons, while most of those from the males were centrally located in the molecule or at the ninth carbon. The female C31 monoolefin stimulated copulation by the males, but more mating activity occurred when the saturated hydrocarbons present in the female cuticular lipids were added. The synthetic monoolefin most active as a mating stimulant pheromone was (Z)-11-hentriacontene, but the addition of female alkanes or of syntheticn-alkanes to (Z)-11-hentriacontene increased the activity of the synthetic pheromone.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 1573-1561
    Keywords: Fannia pusio (Wiedemann) ; pheromone ; mating stimulant pheromone ; (Z)-11-hentriacontene ; cuticular lipid ; fly
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chromatograms of the cuticular lipids washed from newly emerged male and femaleFannia pusio were nearly identical. By the time the flies were 1 day old, the chromatographic profiles for the sexes were different. Mature females contained more C31- and C33-hydrocarbons than the males. The double bonds of the female monoolefins were mostly at the eleventh and thirteenth carbons, but those of the males were predominantly at the ninth carbon. Most active in stimulating copulation by males were the unbranched monoolefins with 31 and 33 carbons from the females. When they were synthesized and tested, the most active compound was (Z)-11-hentriacontene.
    Type of Medium: Electronic Resource
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  • 10
    ISSN: 1573-1561
    Keywords: stable fly ; Stomoxys calcitrans (L.) ; pheromone ; sex pheromone ; C31carbon chain ; C33carbon chain
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Cuticular rinses of the female stable fly,Stomoxys calcitrans (L.), contained saturated and unsaturated hydrocarbons that incited the male fly to attempt couplation. These compounds present in GLC trappings of the saturated hydrocarbon fraction showing highest biological activity were mono- and dimethyl-substituted hentria- and tritriacontanes. Active trappings from the unsaturated hydrocarbon fraction contained (Z)-9-hentriacontene, (Z)-9-tritriacontene, and methyl-branched hentria- and tritriacontenes.
    Type of Medium: Electronic Resource
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