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  • 1
    ISSN: 1573-1561
    Keywords: Spruce budworm ; Choristoneura fumiferana ; Lepidoptera ; Tortricidae ; sex pheromone ; small-tree thinnings ; temperature ; precipitation ; wind ; attraction distance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Mean catches of spruce budworm,Choristoneura fumiferana (Clemens), moths were not significantly different among four small-tree thinning treatments of young spruce-fir-hemlock regeneration. Significant inverse relationships were found between trap catches and distances to nearby spruce-fir-hemlock overstory. Prevailing wind directions indicated that moths were attracted anemotactically to upwind pheromone sources. No definite trends were detected between catches and temperature or precipitation.
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  • 2
    ISSN: 1573-1561
    Keywords: Resistance ; mating disruption ; sex pheromone ; (Z,Z)-7 ; 11-hexadecadienyl acetate ; (Z,E)-7 ; 11-hexadecadienyl acetate ; Lepidoptera ; Gelechiidae ; pink bollworm ; Pectinophora gossypiella ; cotton ; pheromone collection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract After an extensive examination of the release rates and blend ratios of pheromonal components emitted by field-collected femalePectinophora gossypiella (Saunders), we find no evidence of resistance to pheromones applied to cotton fields to disrupt mating. Females from fields with 3–5 years of exposure to disruptant pheromones as well as those from fields with only minimal exposure to disruptant pheromones emitted (Z,Z)-7,11-hexadecadienyl acetate at a rate of ca. 0.1 ng/min and (Z,E)7,11-hexadecadienyl acetate at ca. 0.06 ng/min. The ratio of pheromonal components was much less variable than the measured emission rate and was centered about a 61:39Z, Z to Z,E ratio. In contrast to the blend ratio emitted by females, the composition of the pheromonal blend used in monitoring populations and disrupting mating is centered about 50:50 Z,Z to Z.E. In general there was a remarkable consistency in the release rate and blend ratio among populations of females throughout southern California and those from a laboratory colony. It would appear that, although resistance to theP. gossypiella pheromone is still a very real possibility when it is used heavily in pest management as a mating disruptant, there are current agricultural practices and conditions which would hinder its development.
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  • 3
    ISSN: 1573-1561
    Keywords: Pine sawflies ; Neodiprion spp. ; Hymenoptera ; Diprionidae ; electroantennogram ; sex pheromone ; isomers ; jack pine ; Pinus banksiana ; diprionol ; 3,7-dimethylpentadecan-2-ol ; acetate ; propionate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Several species of monophagous jack pine sawflies (Hymenoptera: Diprionidae) were tested in the field and by electroantennograms (EAG) for activity toward the optical isomers of a pine sawfly sex pheromone, the acetate and propionate esters of 3,7-dimethylpentadecan-2-ol.Neodiprion rugifrons andNeodiprion dubiosus were attracted to a mixture of the propionate esters of the 2S,3R,7R and 2S,3R,7S isomers, whereasNeodiprion swainei was attracted to the 2S,3S,7S propionate isomer. Samples containing the 2S,3R,7S propionate isomer elicited the strongest EAG responses in these three species andNeodiprion nigroscutum. The 2S,3S,7S propionate isomer was equally active (EAG) in the case ofN. swainei.
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  • 4
    ISSN: 1573-1561
    Keywords: Oriental fruit moth ; orfralure ; sex pheromone ; traps ; air permeation with pheromone ; Lepidoptera ; Olethreutinae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Orfralure [93% (Z), 7% (E)-8-dodecen-1-ol acetate], the synthetic pheromone of the oriental fruit moth,Grapholitha molesta (Busck), was released into the air of orchard test plots either by hanging plastic laminated dispensers on trees or by aerial dispersal of microcapsules containing a solution of the lure. Trap catch was reduced 95% or more with the most effective formulations, but consistently higher reductions were produced by the dispensers. In tests as long as 28 weeks with dispensers, a single retreatment at midseason maintained an effective concentration.
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  • 5
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    Journal of chemical ecology 6 (1980), S. 565-572 
    ISSN: 1573-1561
    Keywords: Armyworm ; Mythimna unipuncta ; Pseudaletia unipuncta ; Leucania unipuncta ; Cirphis unipuncta ; Lepidoptera ; sex pheromone ; sex attractant ; (Z)-11-hexadecen-1-ol acetate ; (Z)-9-hexadecen-1-ol acetate ; hexadecan-1-ol acetate ; (Z)-11-hexadecen-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z)-11-Hexadecen-1-ol acetate (Z11–16∶Ac) free of theE isomer (〈1%), hexadecan-1-ol acetate (16∶ Ac), and a hexadecen-1-ol [the (Z)-11 isomer based on the retention time on a Carbowax capillary column] were identified in extracts of the sex pheromone glands of adult virgin female armyworms,Pseudaletia unipuncta. Also, gas Chromatographic retention times on polar and nonpolar columns indicated the possible presence of (Z)-9-hexadecen-1-ol acetate (Z9–16∶Ac). The ratioZ11–16∶Ac/16∶Ac/Z11–16∶OH/Z9–16∶Ac was 1∶0.15∶0.13∶0.02. Infield testsZ11–16∶ Ac was attractive alone, and the addition ofZ9–16∶Ac,Zll–16 ∶ OH, or 16 ∶ Ac singly or in combination in ratios found in the gland did not increase trap capture.
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  • 6
    ISSN: 1573-1561
    Keywords: San Jose scale ; Quadraspidiotus perniciosus ; sex pheromone ; synthesis ; 7-methyl-3-methylene-7-octen-1-yl propanoate ; (E)- and (Z)-3,7-dimethyl-2,7-octadien-1-yl propanoate ; attractant ; Homoptera ; Diaspididae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two components of the San Jose scale sex pheromone had previously been identified as 7-methyl-3-methylene-7-octen-1-yl propanoate (I) and (Z)-3,7-dimethyl-2,7-octadien-1-yl propanoate (II). An isomer and various homologs have subsequently been synthesized and tested in a greenhouse bioassay. TheE isomer of II (XI) was found to be attractive to male scales. This compound has now been isolated and identified from airborne extracts of virgin female scales. The composition of the natural pheromone was 48.5%, 46.7%, and 4.8% of I, II, and XI, respectively. In field tests in California and New York, synthetic XI was found to be attractive to male scales alone and in combination with I and II, but there was no obvious increase in trap catch when the synthetic isomers were present in the same ratio as in the natural blend.
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  • 7
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    Journal of chemical ecology 8 (1982), S. 493-506 
    ISSN: 1573-1561
    Keywords: Choristoneurafumiferana (Clem.) ; Lepidoptera ; Tortricidae ; sex pheromone ; mating disruption ; sex attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male spruce budworm [Chorisloneura fumiferana (Clem.)] moths were held for 3 hr in a wind tunnel and subjected to various concentrations of background synthetic pheromone. They were then exposed to calling females and their response was recorded. The background pheromone was presented either as discrete turbulent plumes or as a uniform permeation throughout the tunnel. The numbers of males wing-fanning and flying in response to the calling females decreased as the concentration of background pheromone increased. Of the males which flew, a higher proportion progressed upwind in the discrete plumes than in the uniform permeation, an indication that structure in the pheromone cloud is necessary for upwind progression. In both discrete plumes and uniform permeation fewer males were able to locate the females (i.e., disruption was greater) as the concentration of synthetic pheromone increased, but for the same total release rates, disruption was greater when the synthetic pheromone was released in discrete plumes rather than in a uniform permeation. This implies that disruption which involves luring males to sources of synthetic pheromone is more effective than masking female plumes by uniform permeation and suggests that it is more efficient to release pheromone from a few potent sources than from numerous low-potency sources.
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  • 8
    ISSN: 1573-1561
    Keywords: Hyalomma dromedarii ; Hyalomma anitolicum excavatum ; ticks ; Acarina ; Ixodidae ; pheromone ; sex pheromone ; 2,6-dichlorophenol ; phenol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 2,6-Dichlorophenol (2,6-DCP) is the major volatile sex pheromone component in the extracts ofHyalomma dromedarii (35 ng/female) andHyalomma anatolicum excavalum (20 ng/female). The GC fraction containing essentially pure 2,6-DCP, as well as an equal amount of synthetic 2,6-DCP, elicits from the male of each species a hierarchy of responses culminating in attempted copulation.
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  • 9
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    Journal of chemical ecology 9 (1983), S. 219-223 
    ISSN: 1573-1561
    Keywords: Synthesis ; sex pheromone ; processionary moth ; Thaume-topoea pityocampa ; Lepidoptera ; Notodontidae ; (Z)-13-hexadecen-11-yn-1-yl acetate ; acetylene ; carbocupration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The synthesis of the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The synthesis uses the carbocupration of acetylene, followed by the coupling with the appropriate 1-iodoalkyne. This synthetic pheromone was shown to be of 98.8%Z purity.
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  • 10
    ISSN: 1573-1561
    Keywords: (Z)-5-Decenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecenyl acetate ; sex attractant ; sex pheromone ; moth ; Agrotis (Scotia) segetum ; Meristis trigrammica ; Hoplodrina alsines ; Erastria trabealis ; Euxoa nigricans ; Lepidoptera Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z)-5-Decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate were tested as single compounds and blends for field attraction to the turnip moth in Denmark, France, Hungary, and Switzerland. Best attraction was obtained when all three components were present. Attractants for other noctuids are described, e.g.,Meristis trigrammica, Hoplodrina alsines, Erastria trabealis, Euxoa nigricans, Axylia putris, andAutographa gamma, which were caught with some of the components and their blends.
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  • 11
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    Journal of chemical ecology 9 (1983), S. 335-346 
    ISSN: 1573-1561
    Keywords: Euxoa drewseni ; Chorizagrotis thanatologia ; Lepidoptera ; Noctuidae ; sex pheromone ; attractant inhibitor ; parapheromone ; (Z)-5-dodecenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-7-tetradecenyl acetate ; (Z)-7-pentadecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Eleven compounds structurally similar to known lepidopterous pheromone components were identified in the extract from 18 calling female moths ofEuxoa drewseni (Staudinger). The identifications were done by gas chromatography-mass spectrometry and high-resolution gas chromatography with flame ionization and electroantennographic detectors simultaneously. Detector antennae were from five species of moths. In the field, male moths were specifically attracted to a three-component blend of dodecyl, (Z)-5-dodecenyl, and (Z)-7-tetradecenyl acetates in a ratio of 2∶6∶1. This blend at 1000 μg/rubber septum dispenser is recommended as a trap bait for monitoring purposes. Low concentrations of (Z)-7-dodecenyl acetate or (Z)-7-tetradecenol inhibited the attraction of moths to the three-component blend. (Z)-7-Pentadecenyl acetate functioned as a parapheromone in place of (Z)-7-tetradecenyl acetate in the pheromone blend, and they appear to react via the same antennal receptor.
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  • 12
    ISSN: 1573-1561
    Keywords: Behavior ; Caenurgina erechtea (Cramer) ; forage looper ; Lepidoptera ; Noctuidae ; sex pheromone ; (Z,Z,Z)-3,6,9-eicosatriene ; (Z,Z,Z)-3,6,9-heneicosatriene ; flight tunnel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z,Z,Z)-3,6,9-Eicosatriene and (Z,Z,Z)-3,6,9-heneicosatriene have been identified as components of the sex pheromone of the noctuid,Caenurgina erechtea (Cramer), the forage looper. Structural assignments were made on the basis of spectroscopic and chromatographic data and were confirmed by comparison with synthetic material. Flight tunnel behavioral studies demonstrated that either component, when tested individually, would elicit wing fanning responses in males; however, mixtures of the two components increased this response and were essential for initiation of upwind flight and landing. In field experiments, traps baited with either component alone captured few or no adult forage looper males while those baited with both components captured several target males.
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  • 13
    ISSN: 1573-1561
    Keywords: Driedfruit moth ; Vitula edmandsae serratilineella ; Lepidoptera ; Pyralidae ; Phycitinae ; sex pheromone ; attractant inhibitor ; (Z)-9,(E)-12-tetradecadienol ; (Z)-9,(E)-12-tetradecadienal ; alcohol ; aldehyde
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sixteen pheromone-like compounds were identified in abdomen tip washes and excised abdomen tip extracts of calling females of driedfruit moth,Vitula edmandsae serratilineella Ragonot. Identifications were by high-resolution gas chromatography-mass spectrometry, and gas chromatography with flame ionization and electroantennographic detectors. Male moths were attracted to a blend of (Z)-9,(E)-12-tetradecadienol and (Z)-9,(E)-12-tetradecadienal in a ratio of 100∶1 at 500 μg/rubber septum dispenser, which is recommended for monitoring purposes. Low concentrations of (Z)-9-tetradecenol (0.5%) and (Z)-9-tetradecenal (0.1%) may be beneficial for the attraction of males, but 1–2% of (E)-9,(E)-12- or (Z)-9,(Z)-12-tetradecadienol, or (Z)-9,(E)-12-tetradecadienyl acetate inhibited their attraction. Gravid female moths were attracted to traps that captured large numbers of males. Females may be attracted to male hairpencil or forewing gland secretions emitted near the traps or that accumulate in the traps.
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  • 14
    ISSN: 1573-1561
    Keywords: Coleoptera ; Chrysomelidae ; Diabrotica ; western corn rootworm ; Mexican corn rootworm ; sex pheromone ; stereospecificity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The four stereoisomers of 8-methyl-2-decyl propanoate were tested in the United States and Mexico for attractiveness toDiabrotica virgifera virgifera LeConte, the western corn rootworm,D. v. zeae Krysan and Smith, the Mexican corn rootworm, andD. porracea Harold. Males ofD. v. virgifera andD. v. zeae responded strongly to the (2R,8R)-isomer and secondarily to (2S,8R), whileD. ponacea responded exclusively to the (2S,8R)-isomer. The (2S,8S)- and (2R,8S)-isomers were inactive in all tests. Synergism or inhibition was not detected when various mixtures of the isomers were tested withD. v. virgifera. These phenomena were not tested withD. v. zeae andD. ponacea.
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  • 15
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    Journal of chemical ecology 10 (1984), S. 973-982 
    ISSN: 1573-1561
    Keywords: Pea moth ; Cydia nigricana (F.) ; Laspeyresia nigricana Steph. ; Lepidoptera ; Olethreutidae ; sex pheromone ; sex attractant ; gas chromatography ; mass spectrometry ; single-ion monitoring ; electroantennography ; (E,E)-8,10-dodecadien-1-yl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone of the pea moth,Cydia nigricana (F.), was identified as (E,E)-8,10-dodecadien-1-ylacetate (E,E8,10–12∶Ac) (approximately 0.1 ng/abdominal tip), in vacuum distillates of virgin female abdominal tips and volatiles emitted by calling females, from its chemical properties and capillary gas chromatography and mass spectrometry data. SyntheticE,E8,10–12∶Ac and the natural pheromone elicited similar quantitative electrophysiological and behavioral responses from male moths. Other related compounds which also attract male moths in the field,viz., (E)-10-dodecen-1-yl acetate, (E,E)-8,10-dodecadien-1-ol, and (E,E)-8,10-dodecadienal, were not detected in the pheromone andE,E8,10–12∶Ac was not found in male moths.
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  • 16
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    Journal of chemical ecology 10 (1984), S. 53-61 
    ISSN: 1573-1561
    Keywords: Melissopus latiferreanus ; Lepidoptera ; Tortricidae ; Olethreutinae ; filbertworm ; sex pheromone ; sex attractant ; (E,E)-8 ; 10-dodecadien-1-ol acetate ; (E,Z)-8,10-dodecadien-1-ol acetate ; conjugated diene isomerization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (E,E)- and (E,Z)-8,10-Dodecadien-1-ol acetates were identified in a 1∶4.3 ratio in the extract of abdominal tips of female filbert-worm moths,Melissopus latiferreanus (Walsingham). The identifications were based on electroantennogram (EAG) analysis, gas chromatography, mass spectrometry, ozonolysis, and synthesis. TheE,Z isomer produced the stronger EAG response. In the field tests of various ratios ofE,E∶E,Z, the ratio found in the extract captured the most males. The pureE,E isomer initially was not attractive by itself (〈0.1%E,Z) but became attractive after a few days, presumably because of isomerization. TheE, Z isomer (〈0.1%E,E) was attractive initially, but this compound might have isomerized faster than theE,E isomer. A study of the isomerization showed that regardless of the initial mixture of 8,10-dodecadien-1-ol acetate isomers, almost complete equilibration existed after one month. The equilibrium mixture consisted of 9%Z8,E10, 65%E8,E10, 23%E8,Z10, and 3%Z8,Z10. Concentrations in rubber septa (1∶4 ratio ofE,E toE,Z) of 0.03–3.0 mg/septum produced equivalent trap catches.
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  • 17
    ISSN: 1573-1561
    Keywords: Dermacentor variabilis ; Acari ; Ixodidae ; tick ; American dog tick ; sex pheromone ; 2,6-dichlorophenol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract No detectable sex pheromone, 2,6-dichlorophenol (2,6-DCP), was found inDermacentor variabilis engorged nymphs, teneral females, replete females, or unfed males. The amount of 2,6-DCP present in unfed females of different ages was extremely variable; no relationship between age and 2,6-DCP content in these unfed females was observed. Partially fed virgin females had less 2,6-DCP than unfed females, but there was no change in pheromone content during the course of feeding. Sex pheromone was also found in partially fed males.
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  • 18
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    Journal of chemical ecology 10 (1984), S. 171-175 
    ISSN: 1573-1561
    Keywords: Aquatic insects ; attractant ; caddisfly ; Gumaga ; odor ; pheromone ; scent ; Sericostomatidae ; sex pheromone ; Trichoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field tests with live, caged females and whole-body extracts of females of the caddisflyGumaga griseola (McLachlan) (Trichoptera: Sericostomatidae) demonstrate, for the first time, the existence of a chemically mediated sexual communication system in this insect order. Both live females and extracts are significantly more attractive to conspecific males than either empty control traps or traps baited withGumaga nigricula (McLachlan) females. Anatomical structures suggest that semiochemicals are widespread in Trichoptera.
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  • 19
    ISSN: 1573-1561
    Keywords: Synthesis ; isomers ; 5,7-dodecadienal ; sex pheromone ; Malacosoma disstria ; Malacosoma californicum ; Lepidoptera ; Lasiocampidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract All four geometrical isomers of 5,7-dodecadien-1-ol have been stereoselectively synthesized by using Wittig condensation reactions. (5 Z,7E)-5,7-Dodecadien-1-ol and its corresponding aldehyde are components of the sex pheromone of the forest tent caterpillar. (5 E,7 Z)-5,7-Dodecadienal is a component of the pheromone of the western tent caterpillar. These compounds have been successfully tested in the field.
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  • 20
    ISSN: 1573-1561
    Keywords: American dog tick ; Dermacentor variabilis ; Acarina ; Ixodidae ; sex pheromone ; mating disruption ; 2,6-dichlorophenol ; control
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Treatment ofD. variabilis-infested dogs with formulations of the sex pheromone, 2,6-dichlorophenol, significantly reduced mating by the attached ticks. Aqueous emulsions of a gelatin microcapsule-xylene slurry and a pheromone-loaded, molecular-sieve powder were used. Concentration was an important variable influencing product efficacy. Such formulations combined with an acaricide may prove effective in reducing tick populations on livestock and pets.
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  • 21
    ISSN: 1573-1561
    Keywords: Red-headed pine sawfly ; Neodiprion lecontei ; Hymenoptera ; Tenthredinidae ; electroantennogram ; field tests ; sex pheromone ; 3,7-dimethylpentadecan-2-yl acetate ; 3,7-dimethylpentadecan-2-yl propionate ; optical isomers ; enantiomers ; esters
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sawfly sex pheromones, the acetate and propionate esters of 3,7-dimethylpentadecan-2-ol, were field tested for activity towardNeodiprion lecontei (Fitch). Only the acetate form of the 2S,3S,7S isomer was active. Field catch decreased with the addition of the 2S,3R,7(R/S) acetate isomer sample. Electroantennogram recordings showed a positive correlation between response and degree to which the chirality of each isomer resembled the attractive isomer.
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  • 22
    ISSN: 1573-1561
    Keywords: (E,Z)-7 ; 9-Dodecadien-1-yl acetate ; European grapevine moth ; Lobesia botrana ; Lepiadoptera ; Tortricidae ; sex pheromone ; purification ; biological activity ; (E,E)-7,9-dodecadien-1-yl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that theE,E isomer does not interfere with the biological activity of the pheromone. It was found that the “crude” preparation has higher activity than purified pheromone or virgin females.
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  • 23
    ISSN: 1573-1561
    Keywords: Agrotis segetum ; turnip moth ; Lepidoptera ; Noctuidae ; sex pheromone ; straight-chain acetates ; single-cell recordings ; electroantennography ; behavior ; gas chromatography-mass spectrometry ; entrainment
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Analysis of female abdominal tips ofAgrotis segetum by means of GC-MS showed the presence of 13 aliphatic acetates and alcohols. (Z)-7-Dodecenyl acetate was found to be the main component in the extracts at amounts of about 1 ng/female. (Z)-9-Tetradecenyl acetate and (Z)-7-dodecenol were present to the extent of 49 and 19%, respectively, of the main component. Minor components could be identified as decyl acetate, (Z)-5-decenyl acetate, dodecyl acetate, (Z)-9-dodecenyl acetate, tetradecyl acetate, a tetradecenyl acetate, hexadecyl acetate, a hexadecenyl acetate, (Z)-5-decenol, and (Z)-9-tetradecenol. The presence and biological activity of decyl acetate, (Z)-5-decenyl acetate, and (Z)-7-dodecenyl acetate in the extracts could be detected by GC-EAD. Tested by EAG (Z)-5-decenyl acetate evoked the highest response among pheromone candidates, followed by (E)-5-decenyl acetate and (Z)-7-dodecenyl acetate. Single-cell recordings from 100 male antennal sensilla trichodea revealed receptorcells highly sensitive to (Z)-5-decenyl, (Z)-7-dodecenyl, (Z)-8-dodecenyl, and (Z)-9-tetradecenyl acetate as well as (Z)-5-decenol. The (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate receptors were activated significantly also by female extracts. When tested in a tube olfactometer, a blend of decyl, (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate evoked the same male response as did female glands. Tested in the field, this blend was more attractive than virgin females. Other authors previously reported many of the compounds identified in the present study. However, both quantitative and qualitative discrepancies exist among the various investigations, possibly due to the existence of geographical races.
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  • 24
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    Journal of chemical ecology 10 (1984), S. 1-7 
    ISSN: 1573-1561
    Keywords: Choristoneura fumiferana ; spruce budworm ; sex pheromone ; pheromone release rates ; (E)-11-tetradecenal ; (Z)-11-tetradecenal ; airborne collection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The rate of pheromone [(E)- and (Z)-11-tetradecenal] release from calling virginChoristoneura fumiferana females and synthetic lures was determined in both static and aerated atmospheres. In a static system ca. 2 ng/hr was recovered per female. Owing to the 〉 75% adsorption onto the females' bodies in static atmospheres, the actual release rate has to be corrected to roughly 9–27 ng/hr, depending on the percentage adsorbed. In the air-flow system, females were found to release between 4 and 20 ng/hr. On a 16∶8 light-dark cycle, calling began 1–2 hr before lights-off and continued nonstop until lights-on. Pheromone was emitted throughout calling, while no pheromone was detected during the noncalling periods.
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  • 25
    ISSN: 1573-1561
    Keywords: Alsophila pometaria (Harris) ; fall cankerworm ; Lepidoptera ; Geometridae ; sex pheromone ; (Z,Z,Z)-3,6,9-nonadecatriene ; (Z,Z,Z,E)-3,6,9,11-nonadecatetraene ; (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone extract from fall cankerworm moths,Alsophila pometaria, attracted conspecific males in field tests. Four EAG-active components were isolated from the extract and identified by GC-MS, highfield PMR spectroscopy, and microchemical techniques asn-nonadecane (I), (Z,Z,Z)-3,6,9-nonadecatriene (II), (Z,Z,Z,E)-3,6,9,11-nonadecatetraene (III), and (Z,Z,Z,Z)-3,6,9,11-nonadecatetrane (IV). Studies of the behavioral responses of male moths in a flight tunnel to the isolated components showed II, III, and IV were the major components of the sex pheromone. No sex pheromone behavioral responses were observed for I.
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  • 26
    ISSN: 1573-1561
    Keywords: Z-9-Dodecenyl acetate ; Z-10-tridecenyl acetate ; dodecyl acetate ; sex pheromone ; synergism ; behavior ; wind tunnel ; field trapping ; European grape moth ; Eupoecilia ambiguella ; Lepidoptera ; Tortricidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Attraction ofE. ambiguella males toZ-9-dodecenyl acetate (Z9-12∶Ac), alone and in combination with dodecyl acetate (12∶Ac) orZ-10-tridecenyl acetate (Z10-13∶Ac) was tested in both wind-tunnel and field experiments. In the laboratory, response toZ9-12∶Ac reached a distinct dosage optimum at which attraction was nearly as good as to live females. Addition of 12∶Ac, a minor component of female glands and effluvia, had no effect at low doses ofZ9-12∶Ac and only marginally improved attraction at the optimum. However, inclusion of 12∶Ac with an overdose ofZ9-12∶ Ac fully restored activity. In the field,Z9-12∶Ac alone was not very attractive at any dose; catches markedly increased by adding 12∶Ac and climbed with increasing dose of each compound up to 10 mg. Optimum ratio ofZ9-12∶Ac to 12∶Ac was 1∶1 to 1∶5. Another compound,Z10-13∶Ac, had the same effect as 12∶Ac in the laboratory and the field but was effective at a lower dose. In the field, inclusion of the synergist permits use of high cap loads to attract more males, perhaps from greater distances.
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  • 27
    ISSN: 1573-1561
    Keywords: Earias insulana ; spiny bollworm ; Lepidoptera ; Noctuidae ; sex pheromone ; (E,E)-10,12-hexadecadienal ; trimerization ; Chromatographic analysis ; nuclear magnetic resonance ; mass spectrometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone ofEarias insulana, (E,E)-10,12-hexadecadienal, may trimerize extensively to form a crystalline trioxane derivative. The structure of the trimer was deduced from its CI-MS and NMR spectra. Capillary GC analysis resulted in the thermal decomposition of the trimer to the monomer. This process could be studied on a 2-m packed column under specific conditions. A convenient separation between the pheromone and its trimer was achieved by TLC. The trimer was inactive in the field, and it has a harmful effect on the performance of the polyethylene dispenser. Material which contains large amounts of the trimer is unsuitable for field use, even if applied at high dosage. The pheromone should be analyzed by NMR or TLC in addition to GC in order to detect the presence of its trimer. The trimerization process is catalyzed by acid which should therefore be completely eliminated from the storing vessels.
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  • 28
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    Journal of chemical ecology 6 (1980), S. 473-485 
    ISSN: 1573-1561
    Keywords: Synthesis ; sex pheromone ; Japanese beetle ; Popillia japonica ; (Z)- and (E)-5-(1-decenyl)dihydro-2(3H)-furanone isomers ; enantiomers of (Z)-5-(1-decenyl)dihydro-2(3H)-furanone
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    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The stereospecific synthesis of the sex pheromone produced by the female Japanese beetle (Popillia japonica Newman), (R,Z)-5-1-decenyl)-dihydro-2(3H)-furanone, is described. The pure syntheticR,Z form is a powerful attractant for males of the species in field bioassays and was competitive in attractiveness with live females, whereas the racemicZ isomer and theS,Z enantiomer were strong inhibitors of male response. The saturated analogs of both enantiomers were also synthesized stereospecifically.
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  • 29
    ISSN: 1573-1561
    Keywords: Electroantennographic detector ; Euxoa ochrogaster ; Lepidoptera ; identification ; mass chromatograms ; mass spectrometry ; redbacked cutworm ; sex pheromone ; (Z)-5-dodecenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-dodecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pheromone washes from calling female moths of redbacked cutworm,Euxoa ochrogaster (Guenée), contained the following acetates that are structurally similar to those of known lepidopteran pheromones (%): decanyl (8.7), dodecanyl (8.5), (E)-5-dodecenyl (3.3), (Z)-5-dodecenyl (76.4), (Z)-7-dodecenyl (3.1), and (Z)-9-dodecenyl (trace〈0.5%). This is the first time that (Z)-5-dodecenyl acetate has been identified as a pheromone component. Three types of specific receptor cells were found in the male antennae, and they responded to (Z)-5-decenyl acetate, (Z)-5- and (Z)-7-dodecenyl acetates, respectively. Strong electroantennographic detector responses were also recorded for these three acetates and for (Z)-5-undecenyl acetate. The evidence for the presence of (Z)-5-decenyl acetate in the pheromone washes was inconclusive. The presence of (Z)-7- and the absence of (Z)-8-dodecenyl acetates were confirmed by a special electroantennographic detector technique in which the detector antennae were from males of other species that were known to have strong responses to these acetates. This is a very useful technique. Field results show that low concentrations (0.1–1.3%) of (Z)-5-decenyl acetate were synergistic when tested in a previously reported blend, but 6% was inhibitory. Similarly, (Z)-7-dodecenyl acetate at 2% or less may be essential for the attraction of males, but in previous tests at 14% it also was inhibitory. Species-specific attractant blends for redbacked cutworm males are described.
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  • 30
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    Journal of chemical ecology 6 (1980), S. 875-881 
    ISSN: 1573-1561
    Keywords: (Z,E)-9,11-Tetradecadienyl acetate ; prodlure ; Egyptian cotton leafworm ; Spodoptera littoralis ; photoisomerization ; sex pheromone ; mass trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Samples of pheromone carriers, after use for 4–5 weeks in traps in the field, were analyzed. Partial isomerization of prodlure, (Z,E)-9,11-tetradecadienyl acetate (TDDA), the main component of the sex pheromone of femaleSpodoptera littoralis, took place. All three other possible isomers were formed to yield a mixture of ∼50% (Z,E)-9,11 -TDDA, ∼30% (E,E)-9,11-, ∼13% (E,Z)-9,11-, and ∼7% (Z,Z)-9,11 isomer. The process was found to be photochemically induced; none of these isomers was found under heating alone. Most of the pheromone, however, decomposed under field conditions.
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  • 31
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    Journal of chemical ecology 7 (1981), S. 285-290 
    ISSN: 1573-1561
    Keywords: Abstinon ; sex pheromone ; Glossina ; Musca ; Diptera ; Muscidae ; homosexual mating inhibitor
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Glossina morsitans morsitans Westwood andMusca domestica Linne have an efficient strategy for preventing wasteful homosexual activity in males: hexane-soluble substances on the cuticle of the male flies terminate courting by other males on contact. The inhibitory activity of these materials is demonstrated by the abstention of males from mating with females treated with male extract.
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  • 32
    ISSN: 1573-1561
    Keywords: Dermacentor variabilis ; Dermacentor andersoni ; 2,6-dichlorophenol ; sex pheromone ; neutral lipid ; sex pheromone glands ; ticks
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Evidence is presented indicating the presence of the tick sex pheromone, 2,6-dichlorophenol in lipid droplets in the foveal glands ofDermacentor variabilis (Say) andDermacentor andersoni Stiles. The pheromone appears to be dissolved in the lipid droplets. The droplets consist of neutral lipids, mostly triacylglycerides and cholesterol esters. The esterified fatty acid profiles of foveal gland triacylgylcerides are different from those of other tissues examined or reported for other ticks. The percentage of shorter chain, mostly saturated fatty acids were decreased, while the longer chain polyunsaturated fatty acids were increased. The biological advantages of lipid solution for storage, translocation, and release of the sex pheromone from the female tick are discussed.
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  • 33
    ISSN: 1573-1561
    Keywords: Disruption of communication ; Oriental fruit moth ; Grapholitha molesta ; Lepidoptera ; Tortricidae ; sex pheromone ; sex attractant ; (Z)-8-dodecenyl acetate ; (E)-8-dodecenyl acetate ; (Z)-8-dodecen-1-ol
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    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The relative efficacy of disruptant blends comprised of different combinations of the Oriental fruit moth's pheromone components was determined in field tests. Disruption was evaluated by comparing male moth catch at synthetic and female-baited traps in disruptant and non-treatment areas. Three atmospheric dosages of a 8-dodecenyl acetate (93.5%Z∶6.5%E) blend, representing two successive 10-fold decreases in concentration (2.5 × 10−2 g/hectare/day to 2.5 × 10−4 g/hectare/day) were tested alone and in combination with an additional percentage of (Z)-8-dodecen-1-ol. Male moth orientation to traps was eliminated in plots exposed to the two highest binary acetate dosages. However, significantly more males were captured in synthetic-baited traps in the lowest acetate-alone treatment, indicating a diminution of disruption efficiency. In contrast, inclusion of (Z)-8-dodecen-1-ol in the disruptant blend effected essentially complete disruption of orientation at all concentrations tested. Mating success ofG. molesta pairs confined in small cages apparently was not affected by the presence of relatively high concentrations of the binary acetate and the acetate-alcohol blends. This suggests that habituation and/or adaptation of male response, at least for comparatively “close-range” behaviors, did not occur.
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  • 34
    ISSN: 1573-1561
    Keywords: American cockroach ; Periplaneta americana ; Orthoptera ; Blattidae ; sex pheromone ; periplanone B ; locomotion ; orientation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Bioassays were performed on malePeriplaneta americana L. using concentrations of (±)-periplanone B of 10−9-10−3 μg and a serial dilution of natural female sex pheromone extract. Synthetic (±)-periplanone B stimulated the complete repertoire of behavior released by the extract: increased rate of locomotion, upwind orientation, and the wingraising component of courtship display. Quantitative behavioral comparisons of the activity of natural extracts prepared by this and other laboratories are possible by the standardization of the stimulus in terms of μg of (±)-periplanone B applied per assay.
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  • 35
    ISSN: 1573-1561
    Keywords: Western avocado leafroller ; Amorbia cuneana ; sex pheromone ; Tortricidae ; (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetate ; Lepidoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The major volatile components in the extract of the female sex pheromone gland ofAmorbia cuneana consisted of (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates. The identification was based on electroantennogram bioassay of gas Chromatographic effluent from sex pheromone gland extract, relative retention times on polar and nonpolar gas chromatographic columns, chemical degradation (ozonolysis, saponification), mass spectrometry, chemical synthetic methods, and field tests. Based on mass spectrometry and retention times by capillary gas chromatography, traces of (E)-10-tetradecen-1-ol acetate and 1-tetradecanol acetate were also present in the extract. Traps baited with a combination of synthetic (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates caught more males than did traps baited with females.
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  • 36
    ISSN: 1573-1561
    Keywords: Western spruce budworm ; Choristoneura occidentalis ; sex pheromone ; attractants ; moth behavior ; chemical identification
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chemical analyses and field bioassays showed a mixture of 92% (E)- and 8% (Z)-11-tetradecenal to be the sex attractant pheromone of the western spruce budworm,Choristoneura occidentalis Freeman. Females were also found to emit small amounts of the corresponding acetates and alcohols, but these components were not active in the bioassay. In contrast, in whole female tip extracts, (E)-11-tetradecenyl acetate predominates, and aldehyde pheromone components are present in lesser quantities, suggesting that final biosynthesis of pheromone takes place just prior to or during emission. At release rates approximating that of the female (2–4 ng/hr), a 92∶8E∶Z blend of the synthetic aldehydes was at least as attractive as live females. Addition of the corresponding acetates or alcohols up to 50% of the aldehyde content did not significantly enhance or inhibit attraction. No major differences were apparent in pheromone production of females from a laboratory stock or from field collections from diverse geographic locations ranging from Colorado to British Columbia.
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  • 37
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    Journal of chemical ecology 8 (1982), S. 545-556 
    ISSN: 1573-1561
    Keywords: Chrysomelidae ; Diabrotica ; western corn rootworm ; northern corn rootworm ; Mexican corn rootworm ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone has been isolated and identified from virgin females of the western corn rootworm (WCR),Diabrotica virgifera virgifera LeConte. The synthesized compound, racemic 8-methyl-2-decanol propanoate, was equal in attraction to the natural pheromone when tested in the field as a trap bait against three taxa ofDiabrotica known to respond to pheromone extracts from female WCR. Five taxa (D. virgifera virgifera; D. virgifera zeae Krysan and Smith, Mexican corn rootworm;D. longicornis barberi Smith and Lawrence, northern corn rootworm;D. longicornis longicornis (Say); andD. porracea Harold) were attracted to traps baited with 8-methyl-2-decanol propanoate. The response of male northern corn rootworms (NCR) in the field peaked at a relatively low concentration of 8-methyl-2-decanol propanoate and then was severely reduced at the higher concentrations tested. Conversely, the response of male WCR in the field continued to increase up to the highest dose tested.
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  • 38
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    Journal of chemical ecology 8 (1982), S. 663-670 
    ISSN: 1573-1561
    Keywords: Pandemis heparana ; sex pheromone ; Lepidoptera ; Tortricidae ; gas chromatography ; mass spectrometry ; insect behavior ; (Z)-11-tetradecen-1-yl acetate ; (Z)-9-tetradecen-1-yl acetate ; (Z)-11-tetradecenl-ol ; tetradecyl acetate ; dodecyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 90% (Z)-11-tetradecen-1-yl acetate, 5% (Z)-9-tetradecen-1-yl acetate, 5% (Z)-11-tetradecen-1-ol, dodecyl acetate (〈1%), and tetradecyl acetate (〈1%) were identified from gland extracts ofPandemis heparana females by gas chromatography and gas chromatography-mass spectrometry analysis (including mass fragmentography studies), chemical characterization, total synthesis, laboratory and field bioassays. In the field, a mixture of (Z)-11-tetradecen-l-yl acetate and (Z)-9-tetradecen-l-yl acetate (95∶5) was found to be essential for attractiveness ofP. heparana males.
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  • 39
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    Journal of chemical ecology 8 (1982), S. 973-980 
    ISSN: 1573-1561
    Keywords: (E, Z)-7,9-Dodecadien-1-yl acetate ; European grapevine moth ; Lobesia botrana ; Lepidoptera ; Tortricidae ; sex pheromone ; photoisomerization ; conjugated diene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Photo- and radical isomerization of (E, Z)-7,9-dodecadien-1-yl acetate (DDA) leads to an equilibrium mixture of all four possible geometric isomers of 7,9-DDA in the ratio ofE,E, 69–76%;Z,E, 11–13%;E, Z, 12–15%; andZ, Z, 1–3%. Iodine catalysis of the isomerization takes place even in dark at room temperature and is probably a radical reaction.
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  • 40
    ISSN: 1573-1561
    Keywords: Sex attractant ; sex pheromone ; processionary moth ; Thaumetopoea pityocampa ; Lepidoptera ; Notodontidae ; (Z)-13-hexadecen-11-ynyl acetate ; field test
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Synthetic (Z)-13-hexadecen-11-ynyl acetate has been shown to be highly active in catchingThaumetopoea pityocampa (Denis and Schiff.) males in field trials carried out in different parts of Spain. A variety of formulations containing antioxidants or solid paraffin were tested. Formulations containing 3 and 10% ofE isomer showed a decrease of activity compared with those prepared with pureZ isomer. Dodecyl acetate, also found in the virgin female gland, did not show any synergistic effect when tested in a 9∶1 mixture with the synthetic pheromone. The product exhibited a remarkable persistence of activity under the field conditions even in the absence of stabilizer.
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  • 41
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    Journal of chemical ecology 9 (1983), S. 1503-1510 
    ISSN: 1573-1561
    Keywords: Methylp-hydroxybenzoate ; sex pheromone ; dog ; Canis familiaris ; Carcidae ; estrous ; chemical communication ; sex stimulant ; sex attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Behavioral studies using anestrous female beagles, and olfactory tests with dogs in the absence of females, indicate that methylp-hydroxybenzoate cannot be considered a key sexual attractant for male beagles, even though this compound has been found in estrous vaginal secretions.
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  • 42
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    Journal of chemical ecology 9 (1983), S. 225-233 
    ISSN: 1573-1561
    Keywords: Synthesis ; sex pheromone ; smaller clear wing moth ; Synanthedon tenuis Lepidoptera ; Sessiidae (Z,Z)-3,13-octadecadien-1-yl acetate ; (Z)-9-tetradecen-1-yl acetate ; carbocupration ; alkylation ; epoxide opening
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The main component of the sex pheromone of the smaller clear wing moth,Synanthedon tenuis, was synthesized. This iterative synthesis uses the carbocupration of acetylene, followed by the alkylation of the (Z)-alkenyl cuprate or by its reaction with ethylene oxide. (Z,Z)-3,13-octadecadien-1-yl acetate, thus obtained, is of 99.8% stereoisomeric purity. An intermediate of the synthesis was (Z)-9-tetradecene-1-yl acetate which is obtained in high yield and 99.9%Z purity.
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  • 43
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    Journal of chemical ecology 9 (1983), S. 259-266 
    ISSN: 1573-1561
    Keywords: Social wasp ; Polistes fuscatus ; Vespidae ; venom ; sex pheromone ; male reproductive behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Females ofPolistes fuscatus possess a sex pheromone in the venom gland and sac. The pheromone attracts males from short distances and releases male copulatory behavior.
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  • 44
    ISSN: 1573-1561
    Keywords: Vapor pressure ; gas chromatography ; sex pheromone ; olefinic acetates ; turnip moth ; Agrotis segetum ; liquid-vapor equilibrium
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    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The vapor pressures of decyl acetate, five decenyl acetate isomers, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate have been determined at three to six temperatures in the interval 25–45 °C by a gas Chromatographic method suitable for accurate measurements of the low vapor pressures of moth sex pheromone components at biologically relevant temperatures. The vapor pressure values at 30.5 °C are 3.80 Pa for decyl acetate, 4.08–5.40 Pa for the decenyl acetate isomers, 0.562 Pa for (Z)-7-dodecenyl acetate, and 0.094 Pa for (Z)-9-tetradecenyl acetate. The vapor pressures of the decenyl acetates show a small but significant dependence on the double bond position. Four of the compounds in this study, 10∶Ac,Z5–10∶Ac,Z7–12∶Ac, andZ9–14∶Ac have recently been identified as sex pheromone components of the turnip moth,Agrotis segetum. Large differences between the mole percentages of the component as found in liquid extracts of female abdominal tips and the corresponding mole percentages in the vapor phase are predicted.
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  • 45
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    Journal of chemical ecology 9 (1983), S. 503-512 
    ISSN: 1573-1561
    Keywords: Epiphyas postvittana ; Lepidoptera ; Fortricidae ; lightbrown apple moth ; sex pheromone ; (E)-11-tetradecen-1-yl acetate ; (E,E)-9,11-tetradecadien-1-yl acetate
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    Notes: Abstract Two compounds, (E)-11-tetradecen-1-yl acetate and (E,E)-9,11-tetradecadien-1-yl acetate, have been identified in extracts of females of the lightbrown apple moth,Epiphyas postvittana (Walker). The two compounds are active as a coalitive pair and are present in extracts of females in a ratio of about 20∶1.
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  • 46
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    Journal of chemical ecology 9 (1983), S. 551-560 
    ISSN: 1573-1561
    Keywords: Synthesis ; nitriles ; acetates ; alcohols ; esters ; pheromone ; attractant ; sex pheromone ; Douglas fir tussock moth ; Orgyia pseudotsugata ; peach fruit moth ; Carposina niponensis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract One-pot conversions of terminai alkynes to cyanoethylated and cyanopropylated alkynes are described. Reactions of these nitriles with Grignard reagents produced alkynones, the reductions of which gave alkenones. The described routes provide 3-step syntheses of several insect sex or stimulatory pheromones, namely, those of the peach fruit moth (Carposina niponensis Walsingham), Douglas fir tussock moth (Orgyia pseudotsugata [McDunnough]), and housefly (Musca domestica L.). Additionally, potentially useful one-pot processes for the preparation of hydroxyalkylated and acetoxyalkylated alkynes are reported.
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  • 47
    ISSN: 1573-1561
    Keywords: Epiphyas postvittana ; Lepidoptera ; Tortricidae ; sex pheromone ; dose-response surface ; isobole ; male response
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    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Bioassay studies with mixtures of the two components from the sex pheromone ofE. postvittana are used to construct a dose-response surface. The surface clearly shows the existence of a response maximum and that an optimum ratio of the two components applies over a wide range of concentrations. Probit transformations of the same data are used to construct an isobologram. The isobole has a sharp minimum at a ratio for the two components close to the ratio produced by the females.
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  • 48
    ISSN: 1573-1561
    Keywords: Tobacco budworm ; Heliothis virescens ; Lepidoptera ; Noctuidae ; flight tunnel ; sex pheromone ; moth behavior ; rubber septa
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    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Each of the seven compounds that have been identified from femaleHeliothis virescens sex pheromone glands was examined for its ability to elicit sexual responses from male moths in a flight tunnel. The two compounds initially described as pheromone components, (itZ)-11-hexadecenal and (itZ)-9-tetradecenal, were necessary for behavioral activity to occur. Of the remaining five compounds, hexadecanal was most consistent in elevating behavioral activity of males when it was added to treatments. Live, calling females elicited greater sexual activity from males than did the 7-compound mixture on rubber septa.
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  • 49
    ISSN: 1573-1561
    Keywords: Coleoptera ; Chrysomelidae ; Diabrotica ; southern corn rootworm ; spotted cucumber beetle ; western spotted cucumber beetle ; sex pheromone ; 10-methyl-2-tridecanone ; ketone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone has been isolated and identified from virgin females of the southern corn rootworm (SCR),Diabrotica undecimpunctata howardi Barber. The synthesized compound, 10-methyl-2-tridecanone was shown to be attractive to males of the SCR, and also to males ofD. u. undecimpunctata Mannerheim, the western spotted cucumber beetle (WSCB), and ofD. u. duodecimnotata in Mexico. Males of both the SCR and the WSCB strongly preferred theR over theS enantiomer. The resolved enantiomers were not tested againstD. u. duodecimnotata.
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  • 50
    ISSN: 1573-1561
    Keywords: (Z)-13-Hexadecen-11-yn-1-yl acetate ; pine processionary moth ; Thaumetopoeapityocampa ; Thaumetopoea wilkinsoni ; Lepidoptera ; Notodontidae ; sex pheromone ; synthesis ; biological activity ; ester
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A short and stereoselective synthesis of (Z)-13-hexadecen-1 1-yn-1-yl acetate is described. The main feature is a low-temperature Wittig reaction of a triphenylpropylphosphonium bromide with a long-chain alkylated propargyl aldehyde.
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  • 51
    ISSN: 1573-1561
    Keywords: Spruce budworm moths ; Choristoneura fumiferana ; Lepidoptera ; Tortricidae ; sex pheromone ; attractants ; isomeric blends
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract E∶Z blends of (E)-11-tetradecenal were field tested (three experiments) for their attractiveness to male spruce budworm,Choristoneura fumiferana (Clemens), moths in northern Maine. Blends of 92.5–99%E isomer caught the most moths (three experiments); blend 95%E had the highest cumulative catch throughout two experiments. Rates of catch per hour for the four most attractive blends (92.5–99%E) showed highly variable responses among experiments; however, similarities were noted for rates of catch within the same experiment. For all experiments and observation hours, blend 95%E had the highest mean rate of catch.
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  • 52
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    Journal of chemical ecology 10 (1984), S. 153-160 
    ISSN: 1573-1561
    Keywords: Choristoneura retiniana ; Lepidoptera ; Tortricidae ; sex pheromone ; sex attractant ; forset insects ; Tortricidae ; insect behavior ; E- andZ-11-tetradecenyl acetates ; E- andZ-11-tetradecenol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sex pheromone components collected from femaleChristoneura retiniana included 11-tetradecenyl acetates and alcohols. The major component wasE-11-tetradecenyl acetate (E11–14∶Ac) with a lesser amount ofZ isomer necessary to induce male response. A 92∶8 ratio ofE,Z11–14∶ Ac appeared optimal. The alcohol component was present at about 10% of the total pheromone mixture, and traps baited with acetates plus alcohol surpassed unmated females in their degree of attractiveness. Chemical analysis indicated a 9∶:1 ratio of theE — Z isomers of 11-tetradecenyl alcohol (11–14∶ol) pheromone components, although bait formulations containing a predominance of either theE orZ isomers were equally successful in field bioassays. Based on male response to traps,E- andZ11–14∶Ac (92∶8E — Z) are essential pheromone components for long-range sex attraction. The 11–14∶ ol enhanced attraction when added at 10% of the total pheromone blend.
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  • 53
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    Journal of chemical ecology 10 (1984), S. 1579-1596 
    ISSN: 1573-1561
    Keywords: Alsophila pometaria(Harris) ; fall cankerworm ; Lepidoptera ; Geometridae ; sex pheromone ; (Z,Z,Z,E)-3,6,9,11-nonadecatetraene ; (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene ; (Z,Z,Z)-3,6,9-nonadecatriene ; synthesis ; hydrocarbons
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z,Z,Z,E)-3,6,9,11-Nonadecatetraene and (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene, sex pheromone components ofAlsophila pometaria, were synthesized by stereoselective Wittig reactions and found to be spectroscopically and chromatographically identical to isolated natural material. Flight-tunnel bioassays and field-trapping experiments confirmed that the two tetraenes together with (Z,Z,Z)-3,6,9-nonadecatriene are sex pheromone components. While traps baited with either tetraene individually captured conspecific males in field-trapping experiments, addition of the triene, which captured no males by itself, to either tetraene resulted in synergistic responses.
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  • 54
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    Journal of chemical ecology 10 (1984), S. 913-921 
    ISSN: 1573-1561
    Keywords: Crab ; Callinectes sapidus ; sex pheromone ; crustecdysone ; molting hormone ; HPLC ; mass spectrometry ; bioassay ; DCI ; desorption chemical ionization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The molting hormone/sex pheromone hypothesis of Kittredge and Takahashi (1972) and Kittredge et al. (1971) was explored inC. sapidus. Two concentrations of crustecdysone (5 × 10−5 M and 5 × 10−6 M) were presented to male crabs in a bioassay system in which courtship behavior was monitored. The results demonstrate that crustecdysone does not stimulate courtship in this species. The physical properties of crustecdysone were also compared to those of the partially purified sex pheromone derived from pubescent females. Using HPLC and mass spectral analysis, no correspondence of crustecdysone with the bioactive material could be shown. These results, in conjunction with the findings of others, do not support an evolutionary relationship between the molting hormone and sex pheromone communication in the Crustacea.
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  • 55
    ISSN: 1573-1561
    Keywords: Corn earworm ; Heliothis zea ; Lepidoptera ; Noctuidae ; flight tunnel ; sex pheromone ; moth behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Each of the four compounds that have been identified from sex pheromone glands ofHeliothis zea female moths was examined for its ability to elicit sexual responses from male moths in a flight tunnel. Males flew upwind to (Z)-11-hexadecenal alone, but greater levels of behavioral activity were evoked with the addition of (Z)-9-hexadecenal to the treatment. Addition of hexadecanal or (Z)-7-hexadecenal to the initial two components had no effect in raising the behavioral response of the males in the flight tunnel whether added singularly at both the normal gland-emission ratio or at varying ratios or in combination at the normal ratio. Live, calling females elicited levels of sexual activity from males not significantly different from that elicited by the mixture of (Z)-11- and (Z)-9-hexadecenal on cotton wicks.
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  • 56
    ISSN: 1573-1561
    Keywords: Pheromonetrap placement ; western spruce budworm ; modoc budworm ; Choristoneura occidentalis ; Choristoneura retiniana ; Lepidoptera ; Tortricidae ; sex pheromone ; sex attractant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pheromone-baited traps located close to both host and nonhost crowns were more attractive than traps located between crowns for bothC. occidentalis Freeman andC. retiniana (Walsingham) at both 10 m and at 1.5 m above the ground. At 10 m height, traps located in host foliage were more attractive than those located in nonhost foliage, but at 1.5m height there was no significant difference. These results were obtained for both dense and sparse populations ofC. occidentalis and sparse populations ofC. retiniana. We conclude that the tree species on which a virgin female is located is not an important factor restricting mating between closely relatedChoristoneura spp. Also, the tree species on which a trap is located may not be an important factor that must be standardized in developing pheromone monitoring systems forC. occidentalis andC. retiniana.
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  • 57
    ISSN: 1573-1561
    Keywords: Sex attractant ; sex pheromone ; lesser peachtree borer ; field test design ; Synanthedon pictipes ; clearwing moths ; Lepidoptera ; Sesiidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Trap capture data from Ohio and Wisconsin show that (E,Z)-3-13-octadecadien-1-ol acetate alone is an effective trap bait for maleSynanthedon pictipes (Grote and Robinson). Attractiveness increased by increasing attractant concentration but not by adding theZ,E geometrical isomer.S. pictipes males partitioned themselves in a linear fashion among traps baited with 10–100 μg of attractant in 10-μg increments. Furthermore, they discriminated between 50- and 100-μg baits placed in the same tree. These and other results indicate that, in clearwing experiments involving noninhibitory compounds and blend tuning, high trap density can be used successfully.
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  • 58
    ISSN: 1573-1561
    Keywords: Furniture carpet beetle ; Anthrenus flavipes ; Coleoptera ; dermestid beetle ; sex pheromone ; (Z)-3-decenoic acid ; aeration apparatus ; Tenax ; gas chromatography ; pentafluorobenzyl bromide ; pheromone release rate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A single-insect aeration apparatus was designed for the study of the pheromone release rate of furniture carpet beetlesAnthrenus flavipes LeConte. Tenax® was selected as the pheromone adsorption agent. The quantity of (Z)-3-decenoic acid (A. flavipes female pheromone) produced per day was estimated by a dose-response curve and bioassay of the collected pheromone. A procedure was established to quantitatively determine the furniture carpet beetle pheromone involving pentafluoro-benzylation of (Z)-3-decenoic acid and subsequent gas chromatographic analysis utilizing flame-ionization and electron-capture detectors.
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  • 59
    ISSN: 1573-1561
    Keywords: Dodecyl acetate ; sex pheromone ; Trichoplusia ni ; Lepidoptera ; Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Dodecyl acetate was identified as a second component of the sex pheromone ofTrichoplusia ni (Hübner). Dodecyl acetate comprised 9.6% by weight of the total pheromone [(Z)-7-dodecenyl acetate plus dodecyl acetate] extracted from glands and 7.3% by weight of the total pheromone evaporated from the surfaces of glands. Dodecyl acetate appears to function as a short-range pheromone component. Evaporation at female release rates of a 10∶90 mixture of dodecyl acetate and (Z)-7-dodecenyl acetate in the field caused a significantly greater percentage of males to land on the pheromone source, increased significantly the time they spent on the source, but decreased significantly the time they spent searching for the source when within 50 cm, as compared to (Z)-7-dodecenyl acetate alone.
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  • 60
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Ostrinia furnacalis ; sex pheromone ; corn borer ; (E)-12-tetradecenyl acetate ; (Z)-12-tetradecenyl acetate ; tetradecyl acetate ; gas chromatography-mass spectrometry ; selected ion monitoring technique
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone components from the corn borer spreading widely in China,Ostrinia furnacalis Guenée, have been identified as (E)-and (Z)-12-tetradecenyl acetates (E andZ12–14∶ Ac). The ratio ofE isomer toZ isomer was 53 ∶ 47. Traps containing 1 × 10−7−1 × 10−5 g of these compounds captured more males than did live females or their tip extract (3–6 female equivalents). Tetradecyl acetate (14 ∶ Ac) was also identified in the tip extract. Its quantity was about 1.8 times the sum of the other two isomers. However, including this compound in its natural ratio in pheromone traps resulted in a decrease in trap catches (P〈 0.05).
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