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  • 1
    Electronic Resource
    Electronic Resource
    Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1549-1570 
    Details
    ISSN: 1573-1561
    Keywords: Coleoptera ; Scarabaeidae ; Oryctes rhinoceros ; coconut rhinoceros beetle ; aggregation pheromone ; pheromone chirality ; ethyl 4-methyloctanoate ; ethyl 4-methylheptanoate ; 4-methyloctanoic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male coconut rhinoceros beetles,Oryctes rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl 4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pheromone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps significantly enhanced attraction. With increasing dose, captures ofO. rhinoceros increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to controlO. rhinoceros in oil palm plantations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02035152
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  • 2
    Electronic Resource
    Electronic Resource
    Structure, chirality, and field testing of a male-produced aggregation pheromone of Asian palm weevilRhynchophorus bilineatus (Montr.) (Coleoptera: Curculionidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1619-1629 
    Details
    ISSN: 1573-1561
    Keywords: Coleoptera ; Curculionidae ; Rhynchophorus bilineatus ; aggregation pheromone ; pheromone chirality ; (4S,5S)-4-methyl-5-nonanol ; coconut palm
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 4-Methyl-5-nonanol is a male-produced aggregation pheromone of the Asian palm weevil,Rhynchophorus bilineatus (Montr.). The pheromone was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometric (MS) analyses of male-and female-produced volatiles. Analyses by GC-EAD and GC-MS of weevil-produced and stereoselectively synthesized isomers of 4-methyl-5-nonanol on a Cyclodex B column, which separated isomers with baseline resolution, revealed that only (4S,5S)-4-methyl-5-nonanol is EAD active and produced by the males. In field experiments in Papua New Guinea, (4S,5S)-4-methyl-5-nonanol and a racemic mixture of disatereoisomers of it enhanced attraction of male and female weevils to sugarcane-baited traps. (4S,5S)-4-Methyl-5-nonanol is also an aggregation pheromone of two other Asian palm weevils.R. ferrugineus (Oliv.) andR. vulneratus (Panz.). The stereoisomeric mixture of 4-methyl-5-nonanol is currently used to manage populations ofR. bilineatus in Papua New Guinea.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02035156
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  • 3
    Electronic Resource
    Electronic Resource
    Two Pheromones of Coniferophagous Bark Beetles Found in the Bark of Nonhost Angiosperms (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 805-816 
    Details
    ISSN: 1573-1561
    Keywords: Semiochemicals ; pheromones ; nonhost volatiles ; frontalin ; conophthorin ; 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane ; (E)-7-methyl-1,6-dioxaspiro[4.5]decane ; Coleoptera ; Scolytidae ; Batesian mimicry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Volatiles from fresh bark of black cottonwood, Populus trichocarpa; trembling aspen, P. tremuloides; paper birch, Betula papyrifera; bigleaf maple, Acer macrophyllum; red alder, Alnus rubra; and Sitka alder, Alnus viridis, were collected on Porapak Q and subjected to coupled gas chromatographic–electroantennographic detection analyses by utilizing the antennae of several scolytid beetles (Dendroctonus pseudotsugae, D. rufipennis, D. ponderosae, Ips pini, and Dryocoetes confusus). Among the antennally active volatiles identified by coupled gas chromatographic-mass spectroscopic analysis were frontalin, 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]-octane, in the two Alnus species and conophthorin, (E)-7-methyl-1,6-diox-aspiro[4.5]decane, in the other four species. Field trapping experiments demonstrated that conophthorin had a significant disruptant effect on the response to a pheromone-host kairomone blend by both Dendroctonus pseudotsugae and D. ponderosae. Our results, and the recent identification of other scolytid pheromones in various tree species, pose major questions regarding the evolution and ecological roles of these semiochemicals, including the possibility of Batesian mimicry by the beetles. They also suggest a need for comparative studies on the biosynthetic pathways for these compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020892700653
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