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  • 4-methyloctanoic acid  (1)
  • Conophthorus banksianae  (1)
  • 1995-1999  (2)
  • 1
    ISSN: 1573-1561
    Keywords: Conophthorus resinosae ; Conophthorus banksianae ; cone beetle ; Scolytidae ; sex pheromone ; repellent ; pityol ; 2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran ; spiroacetal ; 7(E)-methyl-1,6-dioxaspiro[4.5]decane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Analyses of abdominal extracts and beetle-produced volatiles revealed that femaleConophthorus resinosae andC. banksianae produced optically pure (E)-(+)-pityol [(2R,5S)-(+)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran]. In field tests, traps baited with (E)-(±)- or (E)-(+)-pityol captured only males. Addition of host oils to traps baited with pityol did not significantly enhance the capture of males. Males of these former sibling species produced the spiroacetal (5S,7S)-(−)-7-methyl-1,6-dioxaspiro[4.5]decane with high optical purity (96%). Addition of the racemate or the optical isomers of the spiroacetal to traps baited with (E)-(±)-pityol almost completely inhibited the capture of males. It is hypothesized that to ensure their reproductive success, males produce the spiroacetal to repel rival males. Species specificity in pityol and the spiroacetal was not found betweenC. resinosae andC. banksianae, thus supporting their synonymy.
    Type of Medium: Electronic Resource
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  • 2
    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
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