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  • 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
    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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  • 3
    Electronic Resource
    Electronic Resource
    Aggregation pheromone of square-necked grain beetle,Cathartus quadricollis (Guér.) (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 2169-2184 
    Details
    ISSN: 1573-1561
    Keywords: Cathartus quadricollis (Guér.) ; square-necked grain beetle ; Coleoptera ; Cucujidae ; aggregation pheromone ; (3R,6E)-7-methyl-6-nonen-3-yl acetate ; (E)-7-methyl-6-nonen-3-one ; (E)-7-methyl-6-nonen-3-ol ; (6E)-7-methyl-3-propyl-2,6-nonadienyl acetate ; 1-octen-3-ol ; repellent
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract When feeding on rolled oats, male square-necked grain beetles,Cathartus quadricollis (Guér.), produced the aggregation pheromone (3R,6E)-7-methyl-6-nonen-3-yl acetate, for which the trival name “quadrilure” is proposed. The pheromone was highly attractive to both sexes in a two-choice, pitfall olfactometer modified to retain responding beetles by placing a food stimulus (an oat flake) in the glass vials containing the experimental and control stimuli. TheS enantiomer of the pheromone was inactive. Males also produced small amounts of (E)-7-methyl-6-nonen-3-one, (E)-7-methyl-6-nonen-3-ol, and (6E)-7-methyl-3-propyl-2,6-nonadienyl acetate, but these compounds were inactive in the laboratory bioassay. Segregated males and females both produced (R)-(−)-1-octen-3-ol, which by itself was repellent to both sexes but did not diminish beetle response to the aggregation pheromone.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014023
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  • 4
    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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  • 5
    Electronic Resource
    Electronic Resource
    Sites of production and occurrence of volatiles in Douglas-fir beetle,Dendroctonus pseudotsugae hopkins (1988)
    Springer
    Journal of chemical ecology 14 (1988), S. 1305-1317 
    Details
    ISSN: 1573-1561
    Keywords: Douglas-fir beetle ; Dendroctonus pseudotsugae ; Coleoptera ; Scolytidae ; monoterpenes ; volatiles ; frass ; cross-attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Volatiles were found to be distributed throughout adult Douglasfir beetles,Dendroctonus pseudotsugae Hopkins, suggesting that the hindgut may not be the sole site of production. The volatile content of individual beetles increased dramatically with feeding; qualitative changes reflected the different bark habitats of newly emerged and established beetles. All detected volatiles were also found in beetle frass. Myrcene was the predominant monoterpene of emergent beetles and α-pinene of fed beetles. Linalool and bornyl acetate occurred in significant amounts after feeding, and diacetone alcohol and sulcatol were also detected for the first time. The presence of sulcatol explains the reported cross-attraction withGnathotrichus spp.cis-Verbenol was also found to occur in addition totrans-verbenol. The volatile content of male beetles was similar to that of females but amounts of individual compounds were less. Acetic acid was found in both emerged and fed beetles and in lesser amounts in frass, suggesting that microbial metabolism could be a potential source of volatile production.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01019354
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  • 6
    Electronic Resource
    Electronic Resource
    Semiochemicals produced by western balsam bark beetle,Dryocoetes confusus Swaine (Coleoptera: Scolytidae) (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 823-836 
    Details
    ISSN: 1573-1561
    Keywords: Semiochemicals ; pheromones ; enantiomers ; western balsam bark beetle ; Dryocoetes confusus ; Coleoptera ; Scolytidae ; exo- andendo-brevicomin ; trans-verbenol ; verbenone ; myrtenol ; trans-pinocarveol ; cis- andtrans-p-menthen-7-ol ; 3-caren-10-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The most prominent beetle-produced volatiles identified in the abdominal extracts of maleDryocoetes confusus Swaine after they had bored for 24 hr in logs of subalpine fir,Abies lasiocarpa (Hook.) Nutt. were:exo andendo-brevicomin,trans-verbenol, verbenone, myrtenol,trans-pinocarveol,cis- andtrans-p-menthen-7-ol, 3-caren-10-ol, and several monoterpenes and sesquiterpenes. Myrtenol was the only conspicuous compound in extracts from males that had been exposed toA.lasiocarpa resin volatiles for 24 hr. Laboratory bioassays indicated that both (−)- and (+)-exo-brevicomin were attractive to femaleD. confusus, and that the (−) enantiomer did not inhibit response to its antipode. Results from field trapping experiments indicated that bothero-brevicomin and myrtenol are aggregation pheromones forD. confusus.exo-Brevicomin baits were effective in causing attack byD. confusus on baited and surrounding trees, suggesting that this pheromone may have utility in manipulating populations of the beetle.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020163
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  • 7
    Electronic Resource
    Electronic Resource
    Aggregation pheromones of the flat grain beetle,Cryptolestes pusillus (Coleoptera: Cucujidae) (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1053-1070 
    Details
    ISSN: 1573-1561
    Keywords: Cryptolestes pusillus ; coleoptera ; cucujidae ; flat grain beetle ; aggregation pheromone ; macrolide ; (Z)-3-dodecenolide ; (Z)-5-tetradecen-13-olide ; (Z,Z)-3,6-dodecadienolide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Aggregation pheromones were isolated fromCryptolestes pusillus (Schönherr), a coleopteran pest of stored products. Porapak Q-captured beetle and frass volatiles were fractionated by preparative gas-liquid chromatography. The fractions were bioassayed with an arena olfactometer and/or with a two-choice, pitfall olfactometer. Three biologically active, male-produced compounds eliciting aggregation behavior from adultC. pusillus were isolated and identified by spectroscopic methods as (Z)-3-dodecenolide (I), (Z)-5-tetradecen-13-olide (II), and (Z,Z)-3,6-dodecadienolide (III). Compound I was the major volatile produced and was active alone. Compound II was not active alone, but synergized the response to I. Compound III was active alone at higher concentrations, but did not significantly increase the response when added to the most active mixture of I and II, and so it is probably not part of the aggregation pheromone. Pheromone production increased dramatically when the insects were aerated on a food source.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020675
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  • 8
    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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  • 9
    Electronic Resource
    Electronic Resource
    Monoterpene metabolism in female mountain pine beetles,Dendroctonus ponderosae Hopkins, attacking ponderosa pine (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1455-1480 
    Details
    ISSN: 1573-1561
    Keywords: Dendroctonus ponderosae ; mountain pine beetle ; Coleoptera ; Scolytidae ; monoterpene metabolism ; monoterpene alcohols ; pheromones ; allylic hydroxylation ; anti-Markovnikov hydration ; Pinus ponderosa
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Abdominal volatiles of female mountain pine beetles,Dendroctonus ponderosae Hopkins, fed in ponderosa pine,Pinus ponderosa Dougl. ex Laws, and in lodgepole pine,P. contorta var.latifolia Engelmann, were analyzed by gas chromatography and coupled gas chromatography-mass spectrometry and were found to comprise host oleoresin components and beetle-produced alliylic alcohols, aldehydes, and ketones derived from host monoterpenes. Neitherexo- andendo-brevicomin nor frontalin were detected. Three metabolic pathways are proposed to account for the distribution of beetle-produced monoterpene alcohols. The first pathway involves hydroxylation of monoterpene substrates on allylic methyl groups which areE to a methylene or vinyl group. This oxidation pathway is indiscriminate with respect to substrate and probably functions to detoxify monoterpenes. A second pathway, which hydroxylates theendo-cyclic methyleneE to a vinyl methyl group of bicyclic monoterpenes to give almost exclusively thetrans alcohol, is hypothesized to be involved in pheromone production. A third detoxification pathway involves anti-Markovnikov addition of water to theexo-cyclic double bond of β-phellandrene to give predominantlytrans-2-p-menthen-7-ol.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012291
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  • 10
    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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