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  • Coleoptera  (5)
  • Polymer and Materials Science  (4)
  • enantiomers  (3)
  • pheromone  (3)
  • 1
    ISSN: 1573-1561
    Keywords: Sex pheromone ; cigarette beetle ; Lasioderma serricorne (F.) ; Coleoptera ; Anobiidae ; serricornin ; 7-hydroxy-4,6-dimethyl-3-nonanone ; anhydroserricornin ; 2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Reinvestigation of the pheromonal activity of anhydroserricornin, (2S,3S)-2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran, showed that the magnitude of its activity was less than 1/103 of that of serricornin, 7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.). Neither a synergistic nor an inhibitory effect of anhydroserricornin addition on the action of serricornin was observed.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1573-1561
    Keywords: Dacus oleae ; olive fruit fly ; Diptera ; Tephritidae ; pheromones ; enantiomers ; sex attractants ; sex-specific enantiomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 1,7-Dioxaspiro[5.5]undecane (olean), the major component of the female sex attractant pheromone blend of the olive fruit flyDacus oleae (Gmelin) was shown to be released as a racemate. The response of males and females to pure (R)-(−) and (S)-(+)-enantiomers was tested under laboratory and field conditions. Males in laboratory and field tests responded only to (R)-(−)-olean, which functions as a sex attractant. Females responded only to (S)-(+)-olean in laboratory tests but not in the field. There are indications that the latter enantiomer fuctions as a short-range arrestant throughout the day and as an aphrodisiac in the process of mating.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1573-1561
    Keywords: Tsetse fly ; sex stimulant ; pheromone ; hydrocarbon ; methylalkanes ; gas chromatography ; Diptera ; biting fly
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Study of lipids from male and female laboratory-reared flies led to the demonstration of a potent contact sex stimulant in extracts and cuticular hydrocarbons of the female tsetse fly Glossina tachinoides (Westwood) against conspecific males. Thin-layer and column chromatography indicated that extracts contained hydrocarbons and saponifiable lipids. Biological activity was found in the alkanes from females, including prominent branched-chain alkanes that were detected by gas chromatography (GC). The alkanes were separated and collected by preparative gas chromatography (GC), and only the 37-carbon region showed biological activity. GC–mass spectrometry showed the major peak contained a mixture of isomeric 11,23-, 13,25- plus a minor amount of 11,21-dimethylheptatriacontane. Two racemic isomers were synthesized, and bioassays showed that the greatest activity was possessed by the 11,23- isomer with somewhat less activity in 13,25-dimethyl heptatria-contane. Dose–response data showed ED50 at 5 μg per decoy with solvent-washed males, nonspecific females, or corks as decoys. These alkanes released sexual activity in males that comprised most of the behaviors released by a female fly of the same species.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-1561
    Keywords: Sex pheromone ; cigarette beetle ; Lasioderma serricorne (F.) ; Coleoptera ; Anobiidae ; serricornin ; 7-hydroxy-4,6-dimethyl-3-nonanone ; inhibitory action of diastereoisomer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract By adding the effects of a series of the stereoisomers to the pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.) was investigated. The experiments using synthetic enantiomeric mixtures and optically active stereoisomers showed that the (4S,6S,7R)-isomer inhibited significantly the pheromonal activity of serricornin.
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 1573-1561
    Keywords: Mosquito ; Culex pipiens fatigans ; Diptera ; Culicidae ; oviposition ; attractant ; pheromone ; chiral chromatography ; acetoxyhexadecanolide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (−)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (−)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (−)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P 〈 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.
    Type of Medium: Electronic Resource
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  • 6
    ISSN: 1573-1561
    Keywords: Chirality ; enantiomers ; sex pheromones ; (3Z,9Z)-(6R,7S)-epoxynonadecadiene ; (3Z,9Z)-(6S,7R)-epoxynonadecadiene ; (6Z,9Z)-(3S,4R)-epoxynonadecadiene ; Colotois pennaria ; Erannis defoliaria ; Agriopis aurantiaria ; A. marginaria ; A. leucophearia ; Lepidoptera ; Geometridae ; electroantennogram ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts ofColotois pen-Naria, while inErannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-heneicosatriene was indicated inC. Pennaria only. A 10∶10∶3 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catchingC. Pennaria, whileE. Defoliaria males were optimally caught by a 1∶1 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nona-decatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts ofAgriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flyingA. Aurantiaria and the late winter/early spring flyingA. Leucophearia. Males ofAgriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to theS,R-enantiomer increased captures. Optimal catches were recorded with a 10∶3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.
    Type of Medium: Electronic Resource
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  • 7
    ISSN: 1573-1561
    Keywords: Dendroctonus pseudotsugae ; Douglas-fir beetle ; Coleoptera ; Scolytidae ; aggregation pheromone ; production ; response ; methylcyclohexenol ; seudenol ; enantiomers ; trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female Douglas-fir beetles,Dendroctonus pseudotsugae, produced an average 45∶55 mixture of the (S)-(−)- and (R)-(+)-enantiomers of 1-methylcyclohex-2-en-1-ol (MCOL). The (S)-(−)∶(R)-(+) ratio of 3-methylcyclohex-2-en-1-ol (seudenol) produced by this population of females was 34∶66. Lindgren funnel traps baited with (R)-(+)-MCOL attracted significantly more males and females than (S)-(−)-MCOL-baited traps, which captured significantly more beetles than unbaited controls. The combined effect of the enantiomers was additive, rather than synergistic. Either enantiomer of MCOL increased catches by frontalin-baited traps. Racemic MCOL can be used for trapping Douglas-fir beetles in south-central British Columbia.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 1573-1561
    Keywords: Enantiomers ; bark beetle ; pheromone ; Dendroctonus frontalis ; Coleoptera ; Scolytidae ; southern pine beetle ; electrophysiology ; olfaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In laboratory and field bioassays, the response ofDendroctonus frontalis was significantly greater to the mixture of (1S, 5R)-(−)-frontalin andalpha-pinene than to (1R,5S)-(+)-frontalin andalpfa-pinene. Electro-physiological studies revealed that antennal olfactory receptor cells were significantly more responsive to (1S, 5R)-(−)-frontalin than to (1R, 5S)-(+)-frontalin. Both enantiomers stimulated the same olfactory cells which suggests that each cell possesses at least two types of enantiomer-specific acceptors.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 1573-1561
    Keywords: Cryptolestes ferrugineus ; C. pusillus ; Coleoptera ; Cucujidae ; aggregation pheromone ; macrocyclic lactone ; electroantennogram ; behavioural bioassay ; interspecific response ; thermal desorption
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Antennal and behavioral responses of the rust-red grain beetle,Cryptolestes ferrugineus, and the flat grain beetle,C. pusillus, to synthetic samples of the macrocyclic lactones reported to comprise their aggregation pheromones were investigated. Electroantennogram (EAG) recordings were obtained successfully from both species for the first time. Females of both species showed larger EAGs than males. The EAGs ofC. ferrugineus showed a high degree of specificity for conspecific aggregation pheromone components;C. pusillus showed much less specificity. Behavioral tests were conducted using two-choice pitfall bioassays. Separation of the results into the two effects of activity stimulation and direction finding showed that both effects contributed to the overall response, although sometimes to different extents. The strain ofC. pusillus studied responded equally well to both components of its pheromone, whereas it had been reported previously that only one was active, the other acting as a Synergist and eliciting no response when tested alone. With both species, behavioral response was elicited with a single lactone, suggesting that it might not be necessary to use both components for field use. Particularly surprising was thatC. pusillus showed a greater response to the pheromone components ofC. ferrugineus than to its own. Aeration of the two species and thermal desorption of the collected volatiles confirmed production of the expected lactones, and aeration of authentic lactones showed that the response was not due to the C.ferrugineus pheromone components being markedly more volatile. This response, which seems to be an actual preference, is the first to be discovered among the cucujid beetles and encourages optimism that a practical lure for various species may not need to be as complex as originally feared.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Applied Polymer Science 43 (1991), S. 221-225 
    ISSN: 0021-8995
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Studies were made of the thermal softening and degradation behavior in air of low- and high-density polyethylene (PE) grafted with acrylonitrile (AN) by electron beam prior irradiation in nitrogen. It was found that both LDPE and HDPE were made to exhibit higher softening points by grafting and that this tendency increased with increasing percent graft. The starting temperatures of the thermal degradation and thermogravimetric curves were also found to shift to higher temperatures. On the other hand, in marked contrast to the thermal softening and degradation behavior of grafted PE in air, its behavior in nitrogen showed substantial dependance on oxidative degradation, suggesting that the oxidation of PE was inhibited by polyacrylonitrile (PAN), which forms graft chains. It was considered that the oxidation-inhibiting mechanism of PAN produced in the amorphous regions prevents oxygen from dissolving and diffusing into the amorphous phase, thus inhibiting the oxidative degradation of PE, and that, when heated, PAN undergoes nitrile oligomerization and the nitrile oligomer end radicals act to trap those radicals which participate in PE oxidative degradation.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
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