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  • aggregation pheromones  (5)
  • (Z,Z)-5,8-tetradecadien-13-olide  (3)
  • ipsenol  (3)
  • 1
    Electronic Resource
    Electronic Resource
    Enhanced production of aggregation pheromones in four stored-product coleopterans feeding on methoprene-treated oats (1986)
    Springer
    Cellular and molecular life sciences 42 (1986), S. 164-165 
    Details
    ISSN: 1420-9071
    Keywords: Methoprene ; aggregation pheromones ; pheromone production ; stored-product coleopterans ; Oryzaephilus surinamensis ; Oryzaephilus mercator ; Cryptolestes ferrugineus ; Tribolium castaneum ; insect growth regulator ; juvenile hormone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Production of aggregation pheromones by maleOryzaephilus surinamensis, O. mercator, Cryptolestes ferrugineus, andTribolium castaneum was enhanced by feeding on methoprene-treated oats, implicating juvenile hormone in control of pheromone production. Methoprene application to control insects in stored food products may cause enhanced pheromone production by these insects, thus drawing additional beetles into the treated product.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01952448
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  • 2
    Electronic Resource
    Electronic Resource
    Aggregation Pheromone of Pityokteines elegans (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1333-1347 
    Details
    ISSN: 1573-1561
    Keywords: Semiochemical ; secondary attraction ; pheromone ; Pityokteines elegans ; enantiomer ; ipsenol ; ipsdienol ; ipsenone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In laboratory bioassay experiments, the beetles Pityokteines elegans were attracted to volatiles captured from bolts of grand fir, Abies grandis, colonized by P. elegans males. Male-specific volatiles detected by coupled gas chromatographic–electroantennographic detection (GC-EAD) analysis and by GC–mass spectrometry employing a chiral column were: (S)-(−)-ipsenol, (+)- and (−)-ipsdienol, and ipsenone. Field experiments demonstrated that 1:1 combinations of (−)-ipsenol and (±)-ipsdienol strongly attracted insects of both sexes to multiple-funnel traps. No beetles were attracted to any of these compounds alone, and both enantiomers of ipsdienol were required with (−)-ipsenol to induce attraction. Ipsenol and ipsdienol are now reported as pheromones of five Pityokteines species. Specificity of semiochemical-based communication between sympatric P. elegans and P. minutus appears to be based on host preference and on the composition and chirality of the pheromone blend.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006467.79265.3c
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  • 3
    Electronic Resource
    Electronic Resource
    Sex-specific production of ipsdienol and myrcenol byDendroctonus ponderosae (Coleoptera: Scolytidae) exposed to myrcene vapors (1986)
    Springer
    Journal of chemical ecology 12 (1986), S. 1579-1586 
    Details
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; bark beetle ; Coleoptera ; Scolytidae ; myrcene ; aggregation pheromones ; ipsdienol ; myrcenol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male mountain pine beetles,Dendroctonus ponderosae Hopkins, produced ipsdienol [97.0% ± 0.3S-(+)] and myrcenol (90.3% ± 4.0E) when exposed to myrcene vapors. Females which were exposed to myrcene vapors did not produce any ipsdienol, but did produce low levels of myrcenol (98.0% ± 0.7E). Neither sex produced detectable levels of ipsdienol or myrcenol when fed for 24 hr on lodgepole pine,Pinus contorta var.latifolia Engelmann. The sex-specific conversion of myrcene to ipsdienol and myrcenol suggests that these compounds may have behavioral significance within the species. In addition, the S-(+)-ipsdienol produced by maleD. ponderosae probably functions as a repellent allomone againstIps pini (Say).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020265
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  • 4
    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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  • 5
    Electronic Resource
    Electronic Resource
    Aggregation pheromones of the grain beetle,cryptolestes turcicus (Coleoptera: Cucujidae) (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1071-1081 
    Details
    ISSN: 1573-1561
    Keywords: Cryptolestes turcicus ; Coleoptera ; Cucujidae ; aggregation pheromone ; macrolide ; (Z,Z)-5,8-tetradecadien-13-olide ; (Z)-5-tetradecen-13-olide ; enantiomeric synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two biologically active macrolides were isolated from Porapak Q-captured beetle and frass volatiles ofCryptolestes turcicus (Grouvelle) and identified spectroscopically as (Z,Z)-5,8-tetradecadien-13-olide (I) and (Z)-5-tetradecen-13-olide (II). Natural I was active alone and was synergized by inactive II. The pheromones were male-produced but attractive to both sexes. Pheromone production increased dramatically when insects were aerated on a food source. Pure (R)- and (S)-I were inactive, but mixtures of (R)- and (S)-I were active, the first reported instance of enantiomeric synergism in the Cucujidae.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020676
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  • 6
    Electronic Resource
    Electronic Resource
    Aggregation Pheromones and Host Kairomones of West Indian Sugarcane Weevil, Metamasius hemipterus sericeus (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 869-888 
    Details
    ISSN: 1573-1561
    Keywords: Coleoptera ; Curculionidae ; Metamasius hemipterus sericeus ; aggregation pheromones ; pheromone chirality ; (4S, 5S)-4-methyl-5-nonanol ; 2-methyl-4-heptanol ; sugarcane ; ethyl acetate ; ethyl propionate ; ethyl butyrate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses and coupled GC-mass spectrometry (MS) of volatiles produced by male and female West Indian sugarcane weevils (WISW), Metamasius hemipterus sericeus (Oliv.), revealed eight male specific, EAD-active compounds: 3-pentanol (1), 2-methyl-4-heptanol (2), 2-methyl-4-octanol (3), 4-methyl-5-nonanol (4), and the corresponding ketones. In field experiments in Florida, alcohols 1–4 in combination with sugarcane were most attractive, whereas addition of the ketones or replacement of alcohols with ketones significantly reduced attraction. In Costa Rica field experiments testing alcohols 1–4 singly and in all binary, ternary, and quaternary combinations revealed 4 in combination with 2 was the major aggregation pheromone, equally attracting male and female WISW. Stereoisomeric 4 and (4S,5S)-4, the only isomer produced by WISW, were equally attractive. Addition of 4S-, 4R- or (±)-2 to (4S,5S)-4 significantly enhanced attraction. Sugarcane stalks in combination with 2 plus 4 (ratio of 1:8) were highly synergistic, whereas EAD-active sugarcane volatiles ethyl acetate, ethyl propionate, or ethyl butyrate only moderately increased attractiveness of the pheromone lure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006377.13235.4b
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  • 7
    Electronic Resource
    Electronic Resource
    Pheromone production by axenically rearedDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae) (1984)
    Springer
    Journal of chemical ecology 10 (1984), S. 281-290 
    Details
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; Ips paraconfusus ; Coleoptera ; Scolytidae ; axenic rearing ; monoterpenes ; aggregation pheromones ; trans-verbenol ; exo-brevicomin ; ipsenol ; ipsdienol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Mountain pine beetles,Dendroctonus ponderosae Hopkins, and California five-spined ips,Ips paraconfusus Lanier, were reared axenically from surface-sterilized eggs on aseptic pine phloem. After 24 hr in host logs, axenip femaleD. ponderosae and maleI. paraconfusus produced the aggregation pheromones,trans-verbenol (D. ponderosae), and ipsenol and ipsdienol (I. paraconfusus). Emergent, axenically reared maleD. ponderosae contained normal amounts of the pheromoneexo-brevicomin. Axenic femaleD. ponderosae treated with juvenile hormone or exposed to vapors of α-pinene, produced the pheromonetrans-verbenol. By 25–35 days after eclosion, axenic females exposed to α-pinene vapors produced over six times as muchtrans-verbenol as wild females, suggesting that while microorganisms in wild females may producetrans-verbenol, they may also inhibit production of the pheromone or use it as a substrate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987856
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  • 8
    Electronic Resource
    Electronic Resource
    Effect of juvenile hormone analog, fenoxycarb, on pheromone production byIps paraconfusus (Coleoptera: Scolytidae) (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 1087-1098 
    Details
    ISSN: 1573-1561
    Keywords: Juvenile hormone analog ; juvenile hormone ; JH III,Ips paraconfusus ; Coleoptera ; Scolytidae ; bark beetles ; aggregation pheromones ; pheromones ; ipsenol ; ipsdienol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Topical application of the juvenile hormone analog, fenoxycarb, in acetone induced newly emerged male California five-spined ips,Ips paraconfusus Lanier, to become attractive to females, as measured by positive responses to male abdominal extracts in a laboratory bioassay. Two pheromones, ipsdienol and ipsenol, were detected by gas chromatography in the abdominal extracts of fenoxycarb-treated males. Pheromone production was minimal at a dose of 0.1 μg/insect of fenoxycarb, maximal at 10 μg, and was reduced to unmeasurable amounts at a dose of 100 μg. In comparison, peak production of pheromones was induced at a dose of 0.1 μg/insect of natural juvenile hormone (JH III). Treatment with 10 μg of fenoxycarb resulted in the occurrence of pheromones 12 hr after exposure, maximal pheromone content between 16 and 20 hr, and undetectable amounts after 36 hr. The demonstration that fenoxycarb is an active juvenile hormone analog for a bark beetle suggests that it may have practical utility in managing these insects.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01019337
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  • 9
    Electronic Resource
    Electronic Resource
    Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1543-1554 
    Details
    ISSN: 1573-1561
    Keywords: Chiral semiochemicals ; pheromones ; enantiomeric composition ; enantiomeric synergism ; Cryptolestes ferrugineux ; Cryptolestes pusillus ; Cryptolestes turcicus ; Oryzaephilus mercator ; Oryzaephilus surinamensis ; Coleoptera ; Cucujidae ; (Z)-3-dodecen-11-olide ; (Z,Z)-3,6-dodecadien 11-olide ; (Z)-5-tetradecen-13-olide ; (Z,Z)-5,8-tetradecadien-13-olide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012296
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