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  • 1
    Electronic Resource
    Electronic Resource
    Isolation and identification of two macrolide pheromones from the frass ofCryptolestes ferrugineus (Coleoptera: Cucujidae) (1983)
    Springer
    Journal of chemical ecology 9 (1983), S. 451-474 
    Details
    ISSN: 1573-1561
    Keywords: Cryptolestes ferrugineus ; rusty grain beetle ; aggregation ; pheromone ; macrolide ; (E,E)-4,8-dimethyl-4,8-decadien-10-olide ; (3Z,11S)-3-dodecen-11-olide ; (Z,Z)-3,6-dodecadien-11-olide ; (Z)-5-tetradecen-13-olide ; 11-dodecanolide ; 4-nonanolide ; Coleoptera ; Cucujidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two synergistic macrolide aggregation pheromones were isolated from Porapak Q-trapped volatiles obtained from the frass ofCryptolestes ferrugineus (Stephens). These compounds were identified as (E,E)-4,8-dimethyl-4,8-decadien-10-olide (I) and (3Z,11S)-3-dodecen-11-olide (II) and given the trivial names ferrulactone I and II, respectively. Analysis of captured volatiles from separated male and female adults disclosed that the pheromones are male-produced. Additional macrolides were identified in frass volatiles, but were devoid of any pheromonal activity. The structures of I and II were confirmed by comparison with synthetic materials.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00990219
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  • 2
    Electronic Resource
    Electronic Resource
    Influence of pheromone chirality on response byOryzaephilus surinamensis andOryzaephilus mercator (Coleoptera: Cucujidae) (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1525-1542 
    Details
    ISSN: 1573-1561
    Keywords: Oryzaephilus surinamensis ; Oryzaephilus mercator ; aggregation pheromone ; macrolide lactone ; (Z)-3-dodecen-11-olide ; (Z,Z)-3,6-dodecadien-11-olide ; (Z,Z)-5,8-tetradecadien-13-olide ; (Z, Z)-3,6-dodecadienolide ; (Z)-5-tetradecen-13-olide ; enantiomers ; racemate ; chirality ; aggregation behavior ; Coleoptera ; Cucujidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The response of the sawtoothed grain beetle,Oryzaephilus surinamensis (L.), and the merchant grain beetle,O. mercator (Fauvel), to synthetic racemic and chiral macrolide aggregation pheromones was assessed in pitfall olfactometers.O.mercator utilizes theR enantiomers of (Z)-3-dodecen-11-olide and (Z,Z)-3,6-dodecadien-11-olide.O. surinamensis utilizes theR enantiomers of (Z,Z)-3,6-dodecadien-11-olide and the Synergist (Z,Z)-5,8-tetradecadien-13-olide in combination with achiral (Z,Z)-3,6-dodecadienolide. For both species, the racemates of the respective chiral pheromones were effective attractants. The respectiveS enantiomers were inactive for both species and had no effect on the biological activity of the active antipodes. No diel periodicity in responsiveness to pheromones was detected inOryzaephilus spp. reared either on a 12∶12 light-dark photoperiod or in darkness. Nonpheromone macrolides, naturally released in trace amounts byOryzaephilus spp., did not affect the aggregation response of either species to its pheromones when these additional macrolides were combined with the pheromone mixtures.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012295
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