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  • 1
    Electronic Resource
    Electronic Resource
    Identification of a female-produced sex pheromone of the western corn rootworm (1982)
    Springer
    Journal of chemical ecology 8 (1982), S. 545-556 
    Details
    ISSN: 1573-1561
    Keywords: Chrysomelidae ; Diabrotica ; western corn rootworm ; northern corn rootworm ; Mexican corn rootworm ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone has been isolated and identified from virgin females of the western corn rootworm (WCR),Diabrotica virgifera virgifera LeConte. The synthesized compound, racemic 8-methyl-2-decanol propanoate, was equal in attraction to the natural pheromone when tested in the field as a trap bait against three taxa ofDiabrotica known to respond to pheromone extracts from female WCR. Five taxa (D. virgifera virgifera; D. virgifera zeae Krysan and Smith, Mexican corn rootworm;D. longicornis barberi Smith and Lawrence, northern corn rootworm;D. longicornis longicornis (Say); andD. porracea Harold) were attracted to traps baited with 8-methyl-2-decanol propanoate. The response of male northern corn rootworms (NCR) in the field peaked at a relatively low concentration of 8-methyl-2-decanol propanoate and then was severely reduced at the higher concentrations tested. Conversely, the response of male WCR in the field continued to increase up to the highest dose tested.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987802
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  • 2
    Electronic Resource
    Electronic Resource
    Sex pheromone of the face fly,Musca autumnalis De Geer (Diptera: Muscidae) (1975)
    Springer
    Journal of chemical ecology 1 (1975), S. 195-202 
    Details
    ISSN: 1573-1561
    Keywords: face fly ; Musca autumnalis De Geer ; pheromone ; sex pheromone ; behavioral bioassay ; (Z)-14-nonacosene ; (Z)-13-nonacosene ; (Z)-13-heptacosene ; mating strike
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Components of a sex pheromone that cause male face flies to strike at females were found to be the straight-chain monoalkenes (Z)-14-nonacosene, (Z)-13-nonacosene, and (Z)-13-heptacosene. Although these compounds were found in the extracts of both sexes, extracts from sexually mature males contained a much higher proportion of nonacosane and heptacosane, which attenuated the activity of the active monoalkenes. The monoalkenes were readily synthesized by a Wittig reaction modified by the use of hexamethylphosphoric triamide as a cosolvent with tetrahydrofuran to produce a product containing 94–96% (Z) isomer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987868
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  • 3
    Electronic Resource
    Electronic Resource
    Sex pheromone of the stable flyl: Isolation and preliminary identification of compounds that induce mating strike behavior (1975)
    Springer
    Journal of chemical ecology 1 (1975), S. 377-385 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF00988839
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  • 4
    Electronic Resource
    Electronic Resource
    Response of northern corn rootworm,Diabrotica barberi Smith and Lawrence, to stereoisomers of 8-methyl-2-decyl propanoate (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 21-26 
    Details
    ISSN: 1573-1561
    Keywords: Chrysomelidae ; Diabrotica barberi ; northern corn root-worm ; sex pheromone ; stereospecificity ; inhibition ; enantiomer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The four stereoisomers of 8-methyl-2-decyl propanoate were tested in South Dakota for attractiveness to the northern corn rootworm,Diabrotica barberi Smith and Lawrence (NCR). Only the 2R,8R configuration was attractive to the NCR. Inhibition of the NCR response to 2R,8R occurred when either the 2S,8R or 2S,8S isomers were components of the pheromone source. The 2R,8S configuration elicited no behavioral activity in the NCR.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987600
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  • 5
    Electronic Resource
    Electronic Resource
    Response ofDiabrotica virgifera virgifera, D. v. Zeae, andD. porracea to stereoisomers of 8-methyl-2-decyl propanoate (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 1123-1131 
    Details
    ISSN: 1573-1561
    Keywords: Coleoptera ; Chrysomelidae ; Diabrotica ; western corn rootworm ; Mexican corn rootworm ; sex pheromone ; stereospecificity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The four stereoisomers of 8-methyl-2-decyl propanoate were tested in the United States and Mexico for attractiveness toDiabrotica virgifera virgifera LeConte, the western corn rootworm,D. v. zeae Krysan and Smith, the Mexican corn rootworm, andD. porracea Harold. Males ofD. v. virgifera andD. v. zeae responded strongly to the (2R,8R)-isomer and secondarily to (2S,8R), whileD. ponacea responded exclusively to the (2S,8R)-isomer. The (2S,8S)- and (2R,8S)-isomers were inactive in all tests. Synergism or inhibition was not detected when various mixtures of the isomers were tested withD. v. virgifera. These phenomena were not tested withD. v. zeae andD. ponacea.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987518
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  • 6
    Electronic Resource
    Electronic Resource
    Sex pheromone of the stable fly: Evaluation of methyl- and 1,5-dimethylalkanes as mating stimulants (1977)
    Springer
    Journal of chemical ecology 3 (1977), S. 245-249 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF00988440
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  • 7
    Electronic Resource
    Electronic Resource
    Mating-stimulant pheromone and cuticular lipid constituents of the little house fly,Fannia canicularis (L.) (1977)
    Springer
    Journal of chemical ecology 3 (1977), S. 269-278 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF00988443
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis of the male stable fly polyene (Z,Z)-1,7,13-pentacosatriene and its geometrical isomers (1979)
    Springer
    Journal of chemical ecology 5 (1979), S. 415-422 
    Details
    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 four geometrical isomers of 1,7,13-pentacosatriene were synthesized from 1,7-octadiyne. Two of the required isomers were synthesized using known methodology. Hydrogenation of acetylenic linkages were employed to produce predominantly cis alkenes, and alkali metal/amine reduction was used to produce a trans alkene. It was thus possible to produce the (Z,Z) and the (Z,E) isomers. Methods for olefin inversion were then employed to obtain the other two isomers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987926
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  • 9
    Electronic Resource
    Electronic Resource
    An unusual polyene from male stable flies (1977)
    Springer
    Journal of chemical ecology 3 (1977), S. 251-255 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF00988441
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  • 10
    Electronic Resource
    Electronic Resource
    Identification of sex pheromone produced by female sweetpotato weevil,Cylas formicarius elegantulus (Summers) (1986)
    Springer
    Journal of chemical ecology 12 (1986), S. 1489-1503 
    Details
    ISSN: 1573-1561
    Keywords: Cylas formicarius elegantulus ; sweetpotato weevil ; sweet potato ; (Z)-3-dodecen-1-ol (E)-2-butenoate ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone of the sweetpotato weevil,Cylas formicarius elegantulus (Summers), was obtained from collections of volatiles from virgin females, and pheromone was isolated by means of liquid and gas chromatography. The purification procedure was monitored by quantitative laboratory and field bioassays and the compound was identified as (Z)-3-dodecen-1-ol (E)-2-butenoate by means of spectroscopic and microchemical methods. Synthesis, followed by laboratory and field bioassays, showed that the biological activity of the synthetic material was qualitatively and quantitatively indistinguishable from that of the purified natural product.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012367
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