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  • (Z,Z)-11,13-hexadecadienal  (2)
  • Mexican corn rootworm  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Stereospecific synthesis of (Z,Z)-11,13-hexadecadienal, a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae) (1980)
    Springer
    Journal of chemical ecology 6 (1980), S. 221-228 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; navel orangeworm ; Amyelois transitella ; Pyralidae ; (Z,Z)-11,13-hexadecadienal ; (Z,Z)-conjugated diene ; dicyclohexylborane ; conjugated diyne ; liquid crystals for GC
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A synthesis of (Z,Z)-11,13-hexadecadienal, a compound previously identified as the major component of the sex pheromone of the female navel orangeworm,Amyelois transitella (Walker), is described. The key step is the reduction of an unsymmetrical conjugated diyne with dicyclohexylborane. This reduction produced theZ,Z isomer with less than 0.5% total of other isomers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987541
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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Isolation, identification, and synthesis of a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae) (1979)
    Springer
    Journal of chemical ecology 5 (1979), S. 955-966 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; navel orangeworm ; Amyelois transitella ; (Z,Z)-11,13-hexadecadienal ; Pyralidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone of the navel orangeworm,Amyelois transitella (Walker), was obtained from ether rinses of the sex pheromone gland of calling females. The pheromone was isolated by means of liquid and gas chromatography and was identified as one of four possible geometrical isomers of 11,13-hexadecadienal by means of spectroscopic and microchemical methods. Synthesis and laboratory bioassay of all four isomers revealed that only the (Z,Z) isomer was biologically active. (Z,Z)-11,13-hexadecadienal elicited quantitatively similar activation and attraction responses byA. transitella males as did the natural product.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00990218
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  • 4
    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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