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  • Synanthedon pictipes  (2)
  • trimedlure  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Trimedlure enantiomers: Differences in attraction for mediterranean fruit fly,Ceratitis capitata (Wied.) (Diptera: Tephritidae) (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 475-484 
    Details
    ISSN: 1573-1561
    Keywords: Mediterranean fruit fly ; Ceratitis capitata Diptera ; Tephritidae ; attractant ; trimedlure ; stereoisomers ; enantiomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The most biologically active enantiomer of trimedlure, a synthetic lure attractive to male Mediterranean fruit flies, is the 1S,2S,4R enantiomer of isomer C, the fert-butyl ester of ris-4-chloro-trans-2-methylcyclohexanecarboxylic acid. We also determined that the 1R,2R,5S enantiomer of isomer A is significantly more attractive than its optical antipode. Essential differences in the current synthetic work that are critical to possible commercialization of this preparation are detailed herein.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994346
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  • 2
    Electronic Resource
    Electronic Resource
    Structure-activity relationship observations oftrans-trimedlure enantiomers (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 69-79 
    Details
    ISSN: 1573-1561
    Keywords: Insecta ; Ceratitus capitata ; medfly ; trimedlure ; enantiomer ; attractant ; lure ; SAR ; VdW ; Chem-X
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate (TML), a mixture of four majortrans and four minorcis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly),Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (Å3) of the TML structure to male medfly captures. More recently, thetrans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of thetrans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033663
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  • 3
    Electronic Resource
    Electronic Resource
    Response to pheromone traps and disruption of pheromone communication in the lesser peachtree borer and the peachtree borer (Lepidoptera: Sesiidae) (1976)
    Springer
    Journal of chemical ecology 2 (1976), S. 73-81 
    Details
    ISSN: 1573-1561
    Keywords: Synanthedon pictipes ; Sanninoidea exitiosa ; Sesiidae ; pheromone communication disruption ; insect pheromone trapping ; peachtree borer ; lesser peachtree borer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone communication of the lesser peachtree borer,Synanthedon pictipes (Grote and Robinson), and the peachtree borer,Sanninoidea exitiosa (Say), can be disrupted by permeation of the atmosphere with their respective sex pheromones, (E,Z)- and (Z,Z)-3,13-octadecadien-1-ol acetate. The two isomers seemed equally effective against both species. Disruption was greatest when the pheromone was evaporated from the tops of the peach trees; also, pheromone traps placed in the tree tops captured significantly more males than did traps placed lower in the trees. Neither the color nor the directional placement in a tree (NE, NW, SE, SW) of pheromone-baited traps influenced captures of male lesser peachtree borers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00988026
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of sex pheromones of lesser peachtree borer and peachtree borer (1980)
    Springer
    Journal of chemical ecology 6 (1980), S. 271-284 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; attractants ; (E,Z)-3,13-octadecadien-1-ol acetate ; (Z,Z)-3,13-octadecadien-1-ol acetate ; lesser peachtree borer ; Synanthedon pictipes ; peachtree borer ; Synanthedon exitiosa ; 3,13-octadecadien-1-ol isomers ; homopropargylic acetal cleavage ; stereochemistry of dissolving metal reductions
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromones produced by females of the lesser peachtree borer,Synanthedon pictipes (Grote and Robinson), and the peachtree borer,Synanthedon exitiosa (Say), (E,Z)- and (Z,Z)-3,13-octadecadien-1-ol acetate, respectively, were synthesized from 1,8-dichlorooctane, lithium acetylide, and ethylene oxide. In the course of the synthesis a new carbon-oxygen cleavage reaction of homopropargylic acetals was found, and the stereochemistry of the dissolving metal reductions of acetylenic alcohols was investigated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987545
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