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  • 11
    Electronic Resource
    Electronic Resource
    Olefinic acetates, Δ-9,11–14: OAc and Δ-7,9–12: OAc used as sex pheromone components in three geometrid moths,Idaea aversata, I. straminata, andI. biselata (Geometridae, Lepidoptera) (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1505-1526 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; Idaea aversata ; Idaea straminata ; Idaea biselata ; (Z,Z)-9,11-tetradecadienyl acetate ; (Z,Z)-7,9-dodecadienyl acetate ; (Z,E)-7,9-dodecadienyl acetate ; Lepidoptera ; Geometridae ; electroantennography ; single cell recording ; biosynthesis ; phylogeny ; evolution
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts ofIdaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GCEAD). In extracts ofI. straminata, (Z,Z)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species,I. biselata, only (Z,Z)-7,9-dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components inI. aversata andI. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings fromI. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11-tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also inI. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding to (Z,Z)-7,9-dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed inI. straminata. In field tests, a two-component blend containing (Z,Z)-9,11-tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males ofI. aversata. This two-component blend was also attractive to males ofI. straminata, but in a ratio of 1:1. High numbers of maleI. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components ofI. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02027728
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  • 12
    Electronic Resource
    Electronic Resource
    A Genetic Analysis of Population Differences in Pheromone Production and Response Between Two Populations of the Turnip Moth,Agrotis segetum (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1487-1503 
    Details
    ISSN: 1573-1561
    Keywords: Turnip moth ; Agrotis segetum ; Lepidoptera ; Noctuidae ; sex pheromone ; genetics ; population variation ; pheromone production ; behavioral response
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The genetic basis of the differences in female pheromone blend ratio and male behavioral response in the turnip moth,Agrotis segetum, was examined by crossing individuals derived from Scandinavian and Zimbabwean populations. These two populations differ both in the ratio of the three major female pheromone components,Z5–10:OAc,Z7–12:OAc, andZ9–14: OAc and in the behavioral response of the males in both wind-tunnel and field-trapping assays. The female pheromone blend in this study is treated as the log ngZ5–10:OAc/ngZ7–12:OAc and log ngZ9–14:OAc/ngZ7–12:OAc for statistical analysis. The mean log ngZ5–10:OAc/ngZ7–12:OAc, is under control by a major autosomal factor or factors, but it is unclear what genetic factor or factors may control the mean log ngZ9–14:OAc/ngZ7–12:OAc. Frequency distributions of the proportions of each component show wide individual variation and also suggest control ofZ5–10:OAc andZ7–12:OAc by major autosomal factors, which forZ5–10:OAc may show partial dominance. Analysis of male behavioral response to synthetic blends in the wind tunnel yields inconclusive results, but suggests thatA. segetum may have a broad window of response that reflects the range of individual variation in female blends.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/B:JOEC.0000006417.71996.46
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  • 13
    Electronic Resource
    Electronic Resource
    Behavioral responses of male turnip moths,Agrotis segetum, to sex pheromone in a flight tunnel and in the field (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1209-1221 
    Details
    ISSN: 1573-1561
    Keywords: Agrotis segetum ; turnip moth ; Lepidoptera ; Noctuidae ; sex pheromone ; flight tunnel ; decyl acetate ; (Z)-5-decenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecenyl acetate ; (Z)-8-dodecenyl acetate ; field tests ; attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The response of individual male turnip mothsAgrotis segetum was observed in a sustained flight tunnel to a mixture of decyl acetate, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate in proportions similar to those found in gland extracts from virgin females (0.6: 1:5:2.5). Lures containing 3–30 μg (Z)-5-decenyl acetate proved to be maximally attractive, with approximately 60% of the males completing all behavioral steps from activation to copulation efforts. A 300-μg dosage caused significant arrestment of upwind flight. Peak response to synthetics, however, was significantly lower than to female glands. Omitting decyl acetate from the blend did not affect the activity, while omission of any of the three monounsaturated acetates caused a dramatic decrease in response. In the field maximum trap catches were achieved with 1- to 30-μg lures. The subtractive assay carried out in the field confirmed the neutrality of decyl acetate and the importance of the three monoenes. Adding 1% of (Z)-8-dodecenyl acetate (earlier reported as an “inhibitor”) to the four-component mixture decreased the trap catch to about 50%, and increasing the amount of (Z)-8-dodecenyl acetate to 27% decreased the activity further to about 10%. (Z)-8-Dodecenyl acetate also decreased the number of successful flights in the flight tunnel.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01024109
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  • 14
    Electronic Resource
    Electronic Resource
    Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 667-684 
    Details
    ISSN: 1573-1561
    Keywords: Structure-activity ; single-cell recordings ; receptor interaction ; (Z)-5-decenyl acetate ; chain-shortened analogs ; volatility ; vapor pressure ; Agrotis segetum ; Lepidoptera ; Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, have been studied by electrophysiological single-sensillum technique and interpreted in terms of a previously reported receptor-interaction model. The results indicate that the terminal methyl group, as well as the acetate group, interacts with highly complementary receptor sites. The terminal alkyl chain is suggested to interact with a hydrophobic “pocket” extending over the two methylene groups closest to the terminal methyl group. The amounts of stimulus actually released from the odor source have been studied. The results demonstrate the necessity to take differences of volatility into account in comparisons of electrophysiological data for compounds of different chain lengths. It is shown that relative vapor pressures may to a good approximation be employed to estimate correction factors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01016478
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  • 15
    Electronic Resource
    Electronic Resource
    Pheromone variation among eastern European and a western Asian population of the turnip mothAgrotis segetum (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 1611-1622 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; Agrotis segetum ; Lepidoptera ; Noctuidae ; (Z)-5-decenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecenyl acetate ; population variation ; olfactory receptors ; single sensillum response ; gas chromatography ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The female sex pheromone composition and the male electro-physiological response with respect to the three main sex pheromone components, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, were investigated in populations ofAgrotis segetum from Armenia and Bulgaria. The percentage composition of the female-produced pheromone was 1∶52∶47 and 1∶42∶57 for the respective populations. Corresponding male receptor frequencies were 9∶90∶1 and 6∶92∶2. EAG response profiles of the male antennae were similar for the two populations. The populations from Armenia and Bulgaria differed from the earlier investigated French and Swedish populations, which have larger amounts of (Z)-5-decenyl acetate in gland extracts and have a majority of (Z)-5-decenyl acetate-sensitive receptors. Investigation of receptor frequencies on antennae of male Hungarian moths showed that individuals could be classified as either Swedish or Armenian/Bulgarian type. Males of the Swedish type were preferentially attracted to the three-component pheromone blend, whereas blends of (Z)-7-dodecenyl and (Z)-9-tetradecenyl acetate, and (Z)-7-dodecenol [pure or in mixture with (Z)-5-decenol] attracted the Armenian/Bulgarian type. The nature of pheromone variation among European and Asian populations of the turnip moth and possible mechanisms maintaining the variation are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014094
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  • 16
    Electronic Resource
    Electronic Resource
    Pheromone differences between sibling taxaDiachrysia chrysitis (linnaeus, 1758) andD. tutti (Kostrowicki, 1961) (Lepidoptera: Noctuidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 91-109 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Diachrysia chrysitis ; Diachrysia tutti ; pheromones ; sibling taxa ; electroantennographic responses ; biosynthesis ; cross-attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The noctuid sibling taxaDiachrysia chrysitis s. str. andD. tutti, of yet uncertain taxonomic status, have previously been shown to possess differences in morphology and to be attracted to different mixtures of the two presumed pheromone components (Z)-5-decenyl acetate and (Z)-7-decenyl acetate. TypicalD. tutti males (clearly broken forewing marking) are known to respond to a 2: 100 mixture of the two isomers, whereasD. chrysitis males (unbroken marking) are attracted to a 100: 10 mixture. We investigated female pheromone production and male electroantennographic (EAG) response inDiachrysia families raised in the laboratory from field-collected gravid females. Extracts of individual females from typicalD. tutti andD. chrysitis families were subjected to gas chromatography with simultaneous flame ionization and electroantennographic detection. All females produced mixtures of Z5- and Z7-10:OAc, but femaleD. chrysitis produced predominantly Z5-10:OAc and the antennae of their brothers responded more strongly to the Z5 peak than to the Z7-10:OAc peak, whereas the opposite was true forD. tutti families. The pheromone components were shown to be biosynthesized from hexadecanoic and tetradecanoic acid, respectively by Z11-desaturation followed by chain shortening, reduction, and acetylation. The EAG responses of males trapped with the typicalD. tutti andD. chrysitis blends, as well as with an intermediate blend, were investigated. Males trapped with theD. tutti mixture almost exclusively had a clearly broken wing marking and showed strongest EAG response to Z7-10:OAc. The intermediate blend and theD. chrysitis mixture gave more mixed catches, but with a prevalence of males with an unbroken (or almost unbroken) wing marking and with a higher mean response to Z5-10:OAc. Some males with typicalD. tutti EAG responses were attracted in the field to theD. chrysitis pheromone. In the flight tunnel someD. chrysitis males were attracted also to theD. tutti mixture. This indicates that cross attraction may take place between the two taxa under natural conditions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02065993
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  • 17
    Electronic Resource
    Electronic Resource
    Electrophysiological and behavioral responses of turnip moth males,Agrotis segetum to fluorinated pheromone analogs (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 143-157 
    Details
    ISSN: 1573-1561
    Keywords: Agrotis segetum ; Lepidoptera ; Noctuidae ; (Z)-5-decenyl acetate ; fluorinated analogs ; behavioral activity ; electrophysiological activity ; flight tunnel ; single sensillum recording ; field test ; lipophobicity ; lipid solubility ; structure-activity analysis ; pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The electrophysiological and behavioral responses of maleAgrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10∶OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 ∶ OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 ∶ OAc, Z7-12 ∶ OAc, and Z9-14 ∶ OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10∶OAc omitted, the two-component mixture elicited a significantly lower male response. Four analogs, 7,7-F2, 10,10,10-F3, 7,7,8,8-F4, and F9, were added separately to the two-component mixture to replace Z5-10∶OAc. The responses elicited by the mixtures containing the 7,7-F2, 10,10,10-F3, and 7,7,8,8-F4 analogs did not differ significantly from that of the natural three-component mixture and the two-component mixture, whereas the mixture containing F9 elicited a significantly lower male response, as low as the response to the two-component mixture. In a field test the mixtures containing 10,10,10-F3 and 7,7,8,8-F4 were significantly more active than the two-component mixture, but still less active than the natural three-component mixture. It appears that field tests provided greater discrimination among pheromone analogs in assessing their behavioral activity than the flight-tunnel test did. Structure-activity analyses demonstrate the importance of the lipophilic interaction between the terminal alkyl chain and the receptor site for the activity of the stimulus. The lipophobicity of the fluorinated analogs impedes a productive receptor interaction.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987479
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  • 18
    Electronic Resource
    Electronic Resource
    Pheromone specificity inEriocrania semipurpurella (Stephens) andE. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 431-454 
    Details
    ISSN: 1573-1561
    Keywords: Eriocrania semipurpurella ; Eriocrania sangii ; Eriocraniidae ; Lepidoptera ; sex pheromone ; GC-EAD ; chiral gas chromatography ; mass spectrometry ; synthesis ; field trapping ; nonan-2-one ; (Z)-6-nonen-2-one ; (2S,6Z)-nonen-2-ol ; (2R,6Z)-nonen-2-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The fifth abdominal segment of femaleEriocrania semipurpurella (Stephens) andE. sangii (Wood) contains a pair of exocrine glands. Hexane extracts of this segment were prepared from both species and analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). For both species, the EAD active peaks were identified as nonan-2-one, (Z)-6-nonen-2-one, and (Z)-6-nonen-2-ol by means of mass spectrometry and comparison of retention indices with those of synthetic standards. Enantiomeric separation of chiral alcohols from the female extracts was achieved by gas chromatographic analysis on a cyclodextrin column. InE. semipurpurella, a mixture of (2S,6Z)-nonen-2-ol and (2R,6Z)-nonen-2-ol (2: I) was found, whereas inE. sangii (2S,6Z)-nonen-2-ol was the predominant enantiomer and only traces of theR enantiomer were indicated by the antennal response. In field tests, a blend of the three compounds was not attractive to conspecific males. A subtractive assay showed that the alcohol in various enantiomeric mixtures was the only attractive compound, whereas addition of (Z)-6-nonen-2-one to the alcohol completely inhibited the attraction of both species. A trapping experiment including a wide range of ratios between theR andS enantiomers showed that baits containing 95–100% of theS enantiomer were attractive to maleE. sangii, whereas males ofE. semipurpurella were attracted to all tested ratios of the enantiomers. However, the response profiles of maleE. semipurpurella differed between populations from southern Sweden, south Finland, and the Kola Peninsula in Russia. In south Sweden males were maximally attracted to a racemic mixture of the alcohols. At the Kola PeninsulaE. semipurpurella was attracted to baits containing 95–100% of theR enantiomer. In south Finland all tested ratios between 0 and 100%R enantiomer trappedE. semipurpurella, but the trap catches appeared to be bimodally distributed with peaks around 15 and 70%R enantiomer. The trapping results suggest the existence of pheromone races or sibling species among the specimens identified asE. semipurpurella.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033647
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  • 19
    Electronic Resource
    Electronic Resource
    Sex pheromone components of the turnip moth,Agrotis segetum (1982)
    Springer
    Journal of chemical ecology 8 (1982), S. 1305-1321 
    Details
    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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987764
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  • 20
    Electronic Resource
    Electronic Resource
    Individual variation in the pheromone of the turnip moth,Agrotis segetum (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1181-1196 
    Details
    ISSN: 1573-1561
    Keywords: Agrotis segetum ; turnip moth ; Lepidoptera ; Noctuidae ; sex pheromone ; (Z)-5-decenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecenyl acetate ; individual variation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female turnip moths (Agrotis segetum) from a laboratory culture inbred for more than 30 generations, and the offspring (first and third generation) from field-collected insects were analyzed individually for acetates and alcohols in the pheromone gland. Quantitative analysis of individual components was performed at the subnanogram level by gas chromatographymass spectrometry (selected ion monitoring). The titer of the pheromone, i.e., the sum of the homologous acetates (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate was 2.0 ± 0.3 ng in the laboratory culture and 3.2 ± 0.6 ng in the “wild strain.” There was no correlation between pheromone titer and female weight. The relative proportion of the pheromone components varied substantially between individuals, but there was no statistically significant difference between the two populations. The percentages of the respective compounds (¯X ± coefficient of variation) were 14.8 ± 127% for Z5-10:OAc, 55.6 ± 32% for Z7-12:OAc, and 29.6 ± 59% forZ9-14:OAc. The pheromone composition varied more in the wild strain than in the laboratory culture. The significance of the pheromone variation to the attraction of males was tested in a field experiment. The ratio of males trapped by the most attractive blend versus the least attractive one was 2.2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01024107
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