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  • 1
    Electronic Resource
    Electronic Resource
    Specificity of Pheromonal and Kairomonal Response of the Israeli Pine Bast Scale Matsucoccus josephi and Its Predator Elatophilus hebraicus (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1649-1657 
    Details
    ISSN: 1573-1561
    Keywords: Matsucoccus josephi ; Homoptera ; Matsucoccidae ; Elatophilus hebraicus ; Hemiptera ; Anthocoridae ; sex pheromone ; kairomone ; analog
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract It has been demonstrated previously that the sex pheromone of the Israeli pine bast scale, Matsucoccus josephi, (2E,5R,6E,8E)-5,7-dimethyl2,6,8-decatrien-4-one (1) is also a potent kairomone of the scale insect's predator Elatophilus hebraicus. Surprisingly, the sex pheromones of M. feytaudi (2) and M. matsumurae (3) also attract E. hebraicus. These results have prompted us to prepare a series of analogs of 1 with variations in the two moieties attached to the C=O group (4–9) in order to probe the structure–activity relationship of the pheromonal/kairomonal response of M. josephi and E. hebraicus. The most selective and active pheromone analog is 8, attracting only M. josephi males and the most selective and active kairomone analog is the M. feytaudi pheromone 2, attracting only adults of E. hebraicus. A dose–response field test of these analogs and the chiral and racemic M. josephi pheromone 1 indicates that the specificity is maintained at a broad range between 25 and 400 μg corresponding to 1. Analog 5, which is neither a parapheromone nor a kairomone, and analog 8, which is only a parapheromone, are not inhibitory to M. josephi or to E. hebraicus. Our study indicates that alterations in the diene side chain of 1, common to all three Matsucoccus pheromones, strongly reduce the kairomonal activity while structural changes in the second side chain significantly reduce the pheromonal activity. The discovery of selective analogs of 1 has practical implications and enables specific monitoring of M. josephi or E. hebraicus. Particularly important is the possibility to mass-trap males of M. josephi without reducing the population of E. hebraicus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005538929610
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  • 2
    Electronic Resource
    Electronic Resource
    Sex Pheromone Components of Nettle Caterpillar, Setora nitens (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1983-1990 
    Details
    ISSN: 1573-1561
    Keywords: Setora nitens ; Setothosea asigna ; nettle caterpillar ; Limacodidae ; Lepidoptera ; sex pheromone ; (Z)-9-dodecenal ; (Z)-9,11-dodecadienal ; (E)-9-dodecenal ; (E)-9,11-dodecadienal ; oil palm ; Elaeis guineensis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts of female nettle caterpillars, Setora nitens, revealed four compounds that consistently elicited responses from male moth antennae. Retention indices on three fused silia columns (DB-5, DB-23, and DB-210) of two EAD-active compounds were almost identical to those of (E)-9-dodecenal (E9–12 : Ald) and (E)-9,11-dodecadienal (E9,11–12 : Ald), two pheromone components previously identified in congeneric Setothosea asigna. However, comparative GC, GC-EAD, and GC-mass spectrometry of extracted S. nitens compounds and authentic standards revealed that the candidate pheromone components were (Z)-9-dodecenal (Z9–12 : Ald) and (Z)-9,11-dodecadienal (Z9,11–12 : Ald). The two other EAD-active compounds in pheromone gland extracts proved to be the corresponding alcohols to these aldehydes. In field-trapping experiments in Tawau, Malaysia, synthetic Z9–12 : Ald and Z9,11–12 : Ald at a 1 : 1 ratio, but not singly, attracted male S. nitens. Attractiveness of these two aldehydes could not be enhanced through the addition of their corresponding alcohols. Whether these differences in pheromone biology and chemistry between S. nitens and S. asigna are sufficient to prevent cross-attraction of heterospecific males or whether nonpheromonal mechanisms are required to maintain reproductive isolation is currently being studied.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005513211225
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  • 3
    Electronic Resource
    Electronic Resource
    Periodical and Age-related Variation in Chemical Communication System of Black Cutworm Moth, Agrotis ipsilon (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 329-342 
    Details
    ISSN: 1573-1561
    Keywords: sex pheromone ; male response ; calling behavior ; pheromone emission ; periodicity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Periodical and age-related changes in sex pheromone signaling and response were studied in the black cutworm moth, Agrotis ipsilon. Females began to call on the first night after eclosion and called mainly during the second half of the scotophase. The percentage of females calling increased from 1- to 3-day-old females and decreased from 3- to 6-day-old females (P 〈 0.001). One-day-old females called later in the scotophase than 2- and 3-day-old females (P = 0.016). The quantity of Z7–12:Ac, Z9–14:Ac, and Z11–16:Ac in pheromone gland extracts of 1- to 6-day-old females varied with time of the photoregime, increasing during scotophase and decreasing during photophase (P ≤ 0.001). These oscillations were described by using equations containing angular terms with a period of 24 hr. The quantities of Z7–12:Ac and Z9–14:Ac, but not of Z11–16:Ac, varied with female age during the calling period (P 〈 0.001, P = 0.021, and P = 0.529, respectively). The ratios of Z9–14:Ac and Z11–16:Ac to Z7–12:Ac did not change with age or time during calling period. Male response to female pheromone in a wind tunnel increased with age and time of the scotophase. The type of response exhibited by the males (taking flight, oriented flight, and pheromone source contact) was affected by both age and time of the scotophase (P 〈 0.001).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005468203045
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  • 4
    Electronic Resource
    Electronic Resource
    Laboratory and Field Study of the Attraction of Male Pea Midges, Contarinia pisi, to Synthetic Sex Pheromone Components (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1941-1952 
    Details
    ISSN: 1573-1561
    Keywords: Contarinia pisi ; Cecidomyiidae ; Diptera ; sex pheromone ; (2S ; 11S)-diacetoxytridecane ; (2S ; 12S)-diacetoxytridecane ; 2-acetoxytridecane ; wind tunnel ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Behavioral activity of the recently identified sex pheromone components of the pea midge, Contarinia pisi, (2S,11S)-diacetoxytridecane, (2S,12S)-diacetoxytridecane, and 2-acetoxytridecane, was tested in wind tunnel and field-trapping experiments. In the wind tunnel, the attractancy of the three-component blend in a 7 : 10 : 0.1 ratio (following the above order, mimicking the ratios found in gland extract) did not differ significantly from female gland extract, whereas a mixture of the two major components (7 : 10) only attracted 2% of the males to the source. In the field, traps baited with the three-component blend caught by far the largest number of males. Traps baited with the two major components only caught slightly more than the blank traps, and catches in traps baited with 2-acetoxytridecane alone did not differ from catches in the blank traps. Traps baited with the racemate of all three components did not catch more than the blank traps, indicating that some of the enantiomers are inhibitory.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005557026246
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  • 5
    Electronic Resource
    Electronic Resource
    Major Sex Pheromone Component of Female Herald Moth Scoliopteryx libatrix is the Novel Branched Alkene (6Z,13)-Methylheneicosene (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1135-1149 
    Details
    ISSN: 1573-1561
    Keywords: Scoliopteryx libatrix ; Noctuidae ; Lepidoptera ; sex pheromone ; methylalkene ; (6Z13)-methylheneicosene ; electroantennogram ; field test
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The major component of the female-produced sex pheromone of Scoliopteryx libatrix has been characterized by chemical analysis, synthesis, electrophysiological studies and field tests as (6Z,13)-methylheneicosene, probably the 13S-isomer. This is the first example of a branched chain alkene as a sex pheromone in the Noctuidae and is markedly different from the pheromones of other members of the family. The systematic position of S. libatrix, belonging to a monotypic genus of a one-member subfamily within the Noctuidae, may reflect the unusual structure of the sex pheromone.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005475725742
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  • 6
    Electronic Resource
    Electronic Resource
    Repeatability of Pheromone Blend Composition in Individual Males of the Southern Green Stink Bug, Nezara viridula (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 2473-2485 
    Details
    ISSN: 1573-1561
    Keywords: Heteroptera ; Nezara viridula ; sex pheromone ; pheromone variability ; volatile collection ; blend ratio ; solid-phase microextraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The males of Nezara viridula (Heteroptera, Pentatomidae) produce a blend of four terpenoid compounds. The proportion of these four compounds varies among different populations. The terpenoid content of the volatile emission from individual males of a French population was monitored for several days with headspace solid-phase microextraction. The total amount of terpenoid compounds collected on an SPME fiber from one virgin male bug emitting over the course of 1 hr was very variable between samples. More than 50% of males released pheromone, at least during one part of the observation period. The relative percentages of bisabolene, nerolidol, trans-bisabolene epoxide, and cis-bisabolene epoxide were calculated and compared. The proportion of nerolidol in the blend showed a large dispersion between samples and a high coefficient of variation. The percentage values for bisabolene and its trans and cis epoxides were less dispersed, and the coefficients of variation for both epoxides were low. The proportion of trans epoxide relative to the two epoxides, which has been considered characteristic of pheromone strains of N. viridula, showed the smallest coefficient of variation. The repeatability index (RI) varied between 0.57 and 0.85 for the four compounds. Repeatability was particularly high for the two epoxide isomers. Stability in epoxide production was confirmed by statistical analysis (ANOVA), which revealed significant differences in the percentages of cis and trans epoxides between individuals. Correspondingly, the RI of the ratio of trans to cis + trans epoxides was over 0.8. Our study confirms the existence of an interindividual variation of the trans to cis epoxide ratio within populations of Nezara viridula but indicates that each individual reproducibly emits both isomers in the same proportion day after day.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005517410299
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  • 7
    Electronic Resource
    Electronic Resource
    Decadienoates: Sex Pheromone Components of Nettle Caterpillars Darna trima and D. bradleyi (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1969-1981 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Limacodidae ; Darna trima ; Darna bradleyi ; Setothosea asigna ; Setora nitens ; nettle caterpillars ; oil palm ; sex pheromone ; 2-methylbutyl (E)-7,9-decadienoate ; (E)-2-hexenyl (E)-7,9-decadienoate ; methyl (E)-7,9-decadienoate ; isobutyl (E)-7,9-decadienoate ; (E)-9dodecenal ; (E)-9,11-dodecadienal ; (Z)-9-dodecenal ; (Z)-9,11-dodecadienal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic–electroantennographic detection (GCEAD) analyses of pheromone gland extracts revealed two antennally active compounds produced by female D. trima and two by female D. bradleyi. Molecular structures of these candidate pheromone components were identified by electron-impact and chemical-ionization mass spectrometry; retention-index calculations on DB-5, DB-23, and DB-210 columns; microanalytical treatments, as well as syntheses of "auxilliary" compounds that facilitated identification of the compounds. The compounds from D. trima were 2-methylbutyl (E)-7,9-decadienoate (A) and (E)-2-hexenyl (E)-7,9decadienoate (B); from D. bradleyi we identified methyl (E)-7,9-decadienoate (C), and isobutyl (E)-7,9-decadienoate (D). In field experiments in Malaysia, (S)-2-methylbutyl (E)-7,9-decadienoate (SA) in combination with B proved to be essential and synergistic pheromone components for attraction of male D. trima. (R)-2-Methylbutyl (E)-7,9-decadienoate (RA) had no behavioral activity. Compound D singly attracted male D. bradleyi, but addition of C to D at a 1 : 10 ratio significantly enhanced attractiveness of the bait. Synthetic pheromone blends were more effective trap baits than unmated female moths and could be developed for monitoring populations of D. trima and D. bradleyi in Asian oil palm plantations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005561127155
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  • 8
    Electronic Resource
    Electronic Resource
    Identification of Sex Pheromones of Anadevidia peponis and Macdunnoughia confusa and Field Tests of Their Role in Reproductive Isolation of Closely Related Plusiinae Moths (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 443-454 
    Details
    ISSN: 1573-1561
    Keywords: sex pheromone ; lepidopteran attractant ; Noctuidae ; Plusiinae ; (Z)-7-dodecenyl acetate ; (Z)-5-decenyl acetate ; (Z)-9-tetradecenyl acetate ; reproductive isolation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Anadevidia peponis and Macdunnoughia confusa are defoliators of plants in the family Cucurbitaceae and Compositae, respectively, in Japan. GC-MS analyses of crude pheromone gland extracts treated with or without dimethyl disulfide indicated that females of A. peponis produced six monoene acetates and two monoene alcohols and that M. confusa females produced five monoene acetates. These components include (Z)-7-dodecenyl acetate as a major common constituent and three other acetates as minor common constituents. The minor constituents are quite different in blend composition. In addition, with (Z)-7-dodecenyl acetate, an indispensable component for male attraction is (Z)-5-decenyl acetate for A. peponis and (Z)-9-tetradecenyl acetate is essential for M. confusa. Field tests with synthetic lures showed synergistic effects of some other minor components and male attraction of three additional Plusiinae species, Macdunnoughia purissima, Ctenoplusia albostriata, and Chrysodeixis eriosoma, suggesting their reproductive isolation is based in part on pheromonal communication.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005465623518
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  • 9
    Electronic Resource
    Electronic Resource
    1-Methylethyl Octanoate, a New Lepidopteran Sex Pheromone from the Bagworm, Megalophanes viciella (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 487-495 
    Details
    ISSN: 1573-1561
    Keywords: Megalophanes viciella ; Psychidae ; Lepidoptera ; bagworm ; sex pheromone ; 1-methylethyl octanoate ; 2-propyl octanoate ; field tests
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts obtained by rinsing the thorax and extracts from the tergal sex pheromone gland of females of the bagworm moth, Megalophanes viciella, as well as headspace samples from live animals, were analyzed to reveal the chemical structure of the pheromone. As a result, 1-methylethyl octanoate was established as a main sex pheromone component of this species. This was further confirmed by numerous catches of conspecific males in traps baited with this compound in Bulgaria and Roumania.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005421808497
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  • 10
    Electronic Resource
    Electronic Resource
    Comparative Studies of the Ability of Males to Discriminate Between Sexes in Caloglyphus spp. (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1299-1309 
    Details
    ISSN: 1573-1561
    Keywords: Mite ; Acaridae ; sex pheromone ; evolution of signals
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female sex pheromones that trigger the mounting behavior of conspecific males have been identified in four species of the genus Caloglyphus—C. polyphyllae, C. rodriguezi, and two unidentified species. Although the sex pheromones are distributed over both males and females, content ratios of female to male vary from 1.4 in Caloglyphus sp. MJ to 3.4 in C. polyphyllae, 6.3 in C. rodriguezi, and 8.4 in Caloglyphus sp. HP. In the former two species the sex pheromones are also detectable in nymphal stages as a major component, while the pheromones are found to be adult specific in the latter two species. Evaluation of the ability of males to recognize conspecific females revealed that males of all three species, except the Caloglyphus sp. MJ, could discriminate between females and males. We conclude that the differences in the amounts of the female sex pheromone function to facilitate in discrimination by males of conspecific females in the three species, while males of Caloglyphus sp. MJ cannot do this because the 1.4-fold difference is insufficient. It is suggested that the sex pheromone of Caloglyphus spp. might have evolved from a common compound, which originally functioned as a male sexual excitant, into the sex-specific compound that now functions to allow males to discriminate females from males.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005496330285
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  • 11
    Electronic Resource
    Electronic Resource
    Trapping Efficiency and Sex Ratio of Maladera matrida Beetles in Yellow and Black Traps (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 2619-2624 
    Details
    ISSN: 1573-1561
    Keywords: Maladera matrida ; beetle ; Scarabaeidae ; sex pheromone ; trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In field experiments, which started several years ago to investigate the means of chemical communication of the Maladera matrida beetle, we found that the ratio of males to females attracted to the bait (live females with food) was 3 : 2–5 : 4 60 : 40–55 : 45). These findings suggested that an aggregation pheromone is involved in the chemical communication, but the constant small preference for attracted males raised the question whether the active compound(s) is indeed an aggregation pheromone or whether it is a sex pheromone released by the female to attract the male. Since the traps used in our field studies were made of yellow plastic, we had to consider the possibility that the yellow color could have influenced the trapping of the flying beetles and biased the findings for the behavior and mode of attraction toward the source of the chemical communication. To clarify this point, we set out, in this study, to conduct field experiments in which we compared the standard yellow traps with black traps. We found that the bright yellow color did indeed affect the results for chemical communication: The total catch in the yellow traps was double that in black traps, and the male–female ratio in the black traps increased to 4 : 1(80 : 20). This result hints that a sex pheromone, and probably not an aggregation pheromone, as previously thought, is involved in the chemical communication of the M. maladera beetle.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005597031681
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  • 12
    Electronic Resource
    Electronic Resource
    Synergistic Sex Pheromone Components of White-Spotted Tussock Moth, Orgyia thyellina (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 1091-1104 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lymantriidae ; white-spotted tussock moth ; Orgyia thyellina ; (Z)-6-heneicosen-11-one ; (Z)-6-heneicosen-9-one ; (Z)-6,(E)-8-heneicosadien-11-one ; sex pheromone ; synergism ; quarantine insect ; international trade ; eradication ; Bacillus thuringiensis ; microbial insecticide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic–electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6–11-one) and (Z)-6-heneicosen-9-one, the latter termed here “thyellinone.” In field experiments in Japan, Z6–11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997–1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6–11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020833909739
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  • 13
    Electronic Resource
    Electronic Resource
    The Effect of Atmospheric Pheromone Concentrations on Behavior of Lightbrown Apple Moth in an Apple Orchard (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2011-2025 
    Details
    ISSN: 1573-1561
    Keywords: Epiphyas postvittana ; Tortricidae ; sex pheromone ; mating disruption ; threshold concentration ; behavior ; model ; wind
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A previously validated Lagrangian model was used to estimate the threshold of atmospheric pheromone concentration required to prevent trap catch and wing fanning in mating disruption plots in an apple orchard. Electroantennogram (EAG) traces of 10 min duration were recorded, along with supporting meteorological data needed for the model, to better define the conditions in which successful mating disruption will occur. Pheromone was released from polyethylene tubing dispensers into orchard blocks treated with 10, 100, 1000, and 2000 dispensers/ha. Predicted dusk concentrations of atmospheric pheromone at a height of 1.85 m varied nightly between 4 and 90 ng pheromone/m3 (in plots treated with 1000 dispensers/ha) over 11 weeks. Disruption of traps baited with 1000-μg pheromone lures followed an asymptotic curve with predicted concentration, but they did not show a significant effect of trap height (1.5 and 3.0 m). Wing fanning was reduced by increasing the density of dispensers, but was not completely eliminated even at 1000 dispensers/ha. At this density, the concentrations were usually 〈16 ng pheromone/m3. Electroantennogram recordings of 10 min duration showed a higher frequency of pheromone pulses in plots treated with more point sources per hectare. There was also a positive correlation between the number of pulses recorded by the EAG and predicted concentration for plots treated with 1000 or 2000 dispensers/ha. These results give added support to our model of pheromone release and transport in treated apple orchards.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1021028621262
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  • 14
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    Electronic Resource
    Pheromone Components and Diel Periodicity of Pheromonal Communication in Lymantria fumida (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2305-2312 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lymantriidae ; Lymantria fumida ; Lymantria monacha ; nun moth ; sex pheromone ; periodicity ; calling behavior ; reproductive isolation ; disparlure ; (7R,8S)-cis-7,8-epoxy-2-methyloctadecane ; (7S,8R)-cis-7,8-epoxy-2-methyloctadecane ; 2-methyl-Z7-octadecene ; (7R,8S)-cis-7,8-epoxy-octadecane ; (+)-monachalure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts of pheromone glands from female Lymantria fumida were analyzed by coupled gas chromatographic–electroantennographic detection (GC-EAD) and by coupled GC–mass spectrometry (MS). The two compounds that elicited responses from male L. fumida antennae were identified as cis-7,8-epoxy-2-methyloctadecane (disparlure) and 2-methyl-Z7-octadecene (2me-Z7–18Hy). Field experiments in northern Japan demonstrated that synthetic (7R,8S)-cis-7,8-epoxy-2-methyloctadecane [(+)-disparlure] and 2me-Z7–18Hy are synergistic sex pheromone components of L. fumida. (7S,8R)-cis-7,8-Epoxy-2-methyloctadecane [(−)-disparlure] had no behavioral effect on male L. fumida. Traps baited with (+)-disparlure and 2me-Z7–18Hy captured male L. fumida between 21:00 and 24:00 hr, whereas traps baited with (+)-monachalure [(7R,8S)-cis-7,8-epoxy-octadecane], (+)-disparlure and 2me-Z7–18Hy attracted males of the nun moth, L. monacha L., between 02:00 and 04:00 hr. Both temporal separation of pheromonal communication and specificity of pheromone blends seem to contribute to the reproductive isolation of sympatric and coseasonal L. fumida and L. monacha.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020873807864
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  • 15
    Electronic Resource
    Electronic Resource
    Sex-Related Perception of Insect and Plant Volatiles in Lygocoris pabulinus (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2357-2371 
    Details
    ISSN: 1573-1561
    Keywords: Heteroptera ; Miridae ; green capsid bug ; sex pheromone ; electroantennogram ; odors ; plant volatiles ; esters ; (E-2-hexenyl butanoate ; (E)-2-hexen-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract We recorded electroantennograms of male and female Lygocoris pabulinus antennae to 63 insect and plant volatiles. EAGs were between 100 and 500 μV. Overall, male EAGs were about twice the size of female EAGs. In both sexes, largest EAGs were recorded to (E)-2-hexenyl butanoate and (E)-2-hexen-1-ol. Response profiles were similar in both sexes. However, male antennae were more sensitive to a number of esters, especially the butanoates and pentanoates. Female antennae were more sensitive to nine of the 19 plant volatiles, i.e., to hexan-1-ol, heptan-1-ol, 1-octen-3-ol, 2-heptanone, (R)-carvone, linalool, geraniol, nerol, and methyl salicylate. Sexual differences in responses suggest that males are more sensitive to insect-produced pheromone-type compounds, whereas females are more sensitive to plant compounds for their orientation towards oviposition sites.
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    URL: http://dx.doi.org/10.1023/A:1020834226520
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    Airborne Chemical Communication in the Wolf Spider Pardosa milvina (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2527-2533 
    Details
    ISSN: 1573-1561
    Keywords: Pardosa milvina ; Lycosidae ; airborne ; sex pheromone ; wolf spider ; olfactometer ; pitfall traps
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Most studies involving chemical communication in spiders focus on contact pheromones attached to spider silk. Here we tested if males of the wolf spider Pardosa milvina use airborne pheromones to identify, locate, and follow females. Using a two-choice olfactometer, we tested the response of adult male P. milvina to a number of potential chemical cues while controlling for concomitant visual and vibratory stimuli. An airborne chemical cue from adult virgin female P. milvina elicited a positive taxis response from the male. We also tested adult male responses to penultimate instar female P. milvina, one adult male P. milvina, and two adult males together. In each case, test males showed no attraction to the stimuli. Additional experiments were run with pitfall traps baited with adult virgin female P. milvina as attractants. Again, we controlled for visual and vibratory cues from females. Pitfall traps containing virgin females captured significantly more males than control traps. Collectively, these experiments demonstrate evidence of an airborne sex pheromone in P. milvina.
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    URL: http://dx.doi.org/10.1023/A:1020878225553
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    Resolution of Epoxydienes by Reversed-Phase Chiral HPLC and its Application to Stereochemistry Assignment of Mulberry Looper Sex Pheromone (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 1151-1162 
    Details
    ISSN: 1573-1561
    Keywords: Chiral column ; reversed-phase HPLC ; resolution ; sex pheromone ; lepidopteran attractant ; stereochemistry ; epoxydiene ; mulberry looper
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Resolution of insect pheromonal cis-epoxydiene racemates derived from (Z,Z,Z)-3,6,9-trienes was examined with a reversed-phase chiral HPLC column. The results showed that a Chiralcel OJ-R column was suitable for separating the enantiomers having a C17–C23 unsaturated straight chain except for 9,10-epoxydienes with a C21–C23 chain. To determine the absolute configuration of the separated enantiomers, each of the optically active epoxydienes was hydrogenated over Pd-BaSO4 and its behavior was examined on this chiral column by cochromatography with the corresponding chiral epoxy compound having a saturated chain, which was prepared via a Sharpless epoxidation reaction. This analysis showed that the dextrorotatory C17–C23 3,4- and 6,7-epoxydienes and C17–C20 9,10-epoxydienes with shorter R ts possess (3S,4R)-, (6S,7R)-, and (9R,10S) configurations, respectively, and the levorotatory enantiomers with longer R ts possess the opposite configuration. An abdominal tip extract of the mulberry looper, Hemerophila artilineata Butler (Lepidoptera: Geometridae: Ennominae), included (9S,10R)-(Z,Z)-cis-9,10-epoxy-3,6-octadecadiene as a main sex pheromone component. The synthetic (9S,10R)-9,10-epoxydiene, rather than its antipode, elicited strong antennal and behavioral responses from the male moths in electrophysiological and field tests.
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    URL: http://dx.doi.org/10.1023/A:1020894128395
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  • 18
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    Geographic Variation in Sex Pheromone Blend of Hemileuca electra from Southern California (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2505-2525 
    Details
    ISSN: 1573-1561
    Keywords: Hemileuca electra electra ; Hemileuca electra mojavensis ; Hemileuca burnsi ; (10E,12Z)-hexadeca-10,12-dien-1-yl acetate ; (10E,12Z)-hexadeca-10,12-dien-1-ol ; (10E,12Z)-hexadeca-10,12-dienal ; hexadecyl acetate ; sex pheromone ; reproductive character displacement
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Differences were found in the pheromonally mediated mate location systems of two subspecies of Hemileuca electra, H. electra electra (Hee) and H. e. mojavensis (Hem), from southern California. Hem female pheromone gland extracts contained eight times as much (10E,12Z)-hexadeca-10,12-dienal (E10,Z12–16:Ald) and half as much hexadecyl acetate (16:Ac) as Hee extracts. Relative amounts of the other major component of the pheromone blends, (10E,12Z)-hexadeca-10,12-dien-1-ol (E10,Z12–16:OH) did not differ between the two subspecies. In coupled gas chromatography–electroantennogram studies, responses of male antennae to 1:1:1 mixtures of the three principal components (E10,Z12–16:Ac, E10,Z12–16:OH, E10,Z12–16:Ald) also differed, with Hem antennae producing significantly larger responses to E10,Z12–16:Ald and significantly smaller responses to 10E,12Z–16:Ac than Hee. In field trials, male Hem were attracted to Hem females in preference to Hee females. Males of a second species, H. burnsi, which is sympatric with Hem but not Hee, also were attracted to females of Hee transported to their range. Field tests of blends of synthesized pheromone components confirmed that male Hem preferred E10,Z12–16:Ald ratios of 10–100% of the major component, E10,Z12–16:Ac, whereas males of Hee and H. burnsi responded optimally to ratios of 0.3–1% E10,Z12–16:Ald to E10,Z12–16:Ac. 16:Ac added to lures increased attraction of Hee but not Hem males. The data presented are consistent with reproductive character displacement, whereby the Hem subspecies has modified its pheromone-based mating system to reduce interference from sympatric H. burnsi.
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    Sex Pheromone Components of Casuarina Moth, Lymantria xylina (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2535-2545 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lymantriidae ; Lymantria xylina ; Lymantria dispar ; Lymantria monacha ; Lymantria fumida ; sex pheromone ; reproductive isolation ; (7R,8S)-cis-7,8-epoxy-2-methyleicosane ; (7S,8R)-cis-7,8-epoxy-2-methyleicosane ; 2-methyl-Z7-eicosene ; (7R,8S)-cis-7,8-epoxy-2-methylnonadecane ; (7S,8R)-cis-7,8-epoxy-2-methylnonadecane ; (7R,8S)-cis-7,8-epoxy-3-methylnonadecane ; (7S,8R)-cis-7,8-epoxy-3-methylnonadecane ; disparlure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract cis-7,8-Epoxy-2-methyleicosane is a sex pheromone component of the Casuarina moth, Lymantria xylina Swinhoe. The compound was extracted from pheromone glands of female moths and was identified by coupled gas chromatographic–electroantennographic detection (GC-EAD) and GC–mass spectrometry. In field experiments in Taiwan, traps baited with either or both of (7R,8S)-cis-7,8-epoxy-2-methyleicosane (〉99% ee) [termed here (+)-xylinalure] and (7S,8R)-cis-7,8-epoxy-2-methyleicosane (〉99% ee) [termed here (−)-xylinalure] captured male L. xylina. Addition of further candidate pheromone components to xylinalure did not enhance its attractiveness. Demonstration of whether or not female L. xylina produce both optical isomers of xylinalure, and determination of the ratio, will require pheromone extract analyses on a chiral, enantiomer-separating column (as yet unavailable) or derivatization of epoxides in accumulated gland extracts. Attraction of male L. xylina to either enantiomer of xylinalure contrasts with enantiospecific production of, and/or response to, epoxy pheromones in congeners. With no other nocturnal lymantriid moth known in Taiwan to utilize xylinalure for pheromonal communication, enantiospecific “fine tuning” of xylinalure, or evolution of a more complex pheromone blend, may not have been necessary for L. xylina to maintain specificity of sexual communication. Racemic xylinalure will be appropriate for pheromone-based detection surveys of L. xylina in North America.
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    Identification and Field Evaluation of Components of Female Sex Pheromone of Millet Stem Borer, Coniesta ignefusalis (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 2643-2663 
    Details
    ISSN: 1573-1561
    Keywords: Coniesta ignefusalis ; Acigona ignefusalis ; Lepidoptera ; Pyralidae ; sex pheromone ; (Z)-7-dodecen-1-ol ; (Z)-5-decen-1-ol ; (Z)-7-dodecenal ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecen-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatography (GC) linked to electroantennographic (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7–12:OH), (Z)-5-decen-1-ol (Z5–10:OH), (Z)-7-dodecenal (Z7–12:Ald), (Z)-7-dodecenyl acetate (Z7–12:Ac), and (Z)-9-tetradecen-1-ol (Z9–14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards. Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7–12:OH, and two of the minor components, Z5–10:OH and Z7–12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7–12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7–12:Ac and/or Z9–14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.
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  • 21
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    Sex Pheromone of the Common Sheep Moth, Hemileuca eglanterina, from the San Gabriel Mountains of California (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 687-709 
    Details
    ISSN: 1573-1561
    Keywords: Hemileuca eglanterina ; E10,Z12-hexadeca-10,12-dien-1-yl acetate ; E10,Z12-hexadeca-10,12-dien-1-ol ; E10,Z12-hexadeca-10,12-dienal ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone of Hemileuca eglanterina from the San Gabriel Mountains, California, was determined to be a combination of E10,Z12-hexadeca-10,12-dien-1-yl acetate, E10,Z12-hexadeca-10,12-dien-1-ol, and E10,Z12-hexadeca-10,12-dienal. Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100 : 48 : 1.1 of the acetate, alcohol, and aldehyde, respectively. Field trials with synthetic compounds indicated that the optimum ratio of alcohol to aldehyde was 10 : 1 and that this ratio was more critical than the ratio of either compound to the acetate. A synthetic blend of 100 : 10 : 1 acetatendash;alcoholndash;aldehyde was effective at attracting male moths in the field. Additional compounds found in both extract and aeration samples failed to significantly increase trap catches of male moths, although some of these minor components elicited responses from male moth antennae in coupled gas chromatography–electroantennography studies.
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    URL: http://dx.doi.org/10.1023/A:1020876229787
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  • 22
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    Subtleties in Perception and Discrimination by Cabbage Looper Moths, Trichoplusia ni, of the two 14-carbon Acetate Sex Pheromone Components (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 455-469 
    Details
    ISSN: 1573-1561
    Keywords: T. ni ; sex pheromone ; behavior ; perception ; flight ; orientation ; trapping ; wind tunnel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three compounds that are emitted by virgin female cabbage looper moths, Trichoplusia ni, (Z)-7-dodecenyl acetate (Z7–12:Ac), (Z)-7-tetradecenyl acetate (Z7–14:Ac), and (Z)-9-tetradecenyl acetate (Z9–14:Ac), are detected by antennal olfactory receptor neurons specialized to detect sex pheromone components. The principal evidence signifying that either or both of Z7–14:Ac and Z9–14:Ac have an effect on male behavior comes from an observed reduction in the numbers of males trapped by Z7–12:Ac paired with a six-component mixture. The evidence conforms to a hypothesis that either or both of these compounds are the basis for discrimination between the two mixtures. However, scant evidence for this hypothesis was obtained in paired-source laboratory wind-tunnel assays, even at airborne concentrations of Z7–14:Ac and Z9–14:Ac that ranged up to 1000× that emitted by a female. Furthermore, there was little evidence from single-source laboratory or field trap assays confirming that Z7–14:Ac and Z9–14:Ac at or above natural stimulus strengths modify the moth's perception of Z7–12:Ac. The data suggest that discrimination of small mixture differences may not be resolvable within the confines of a wind tunnel.
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    Simultaneous Disruption of Pheromone Communication in Choristoneura rosaceana and Pandemis limitata with Pheromone and Antagonist Blends (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 501-517 
    Details
    ISSN: 1573-1561
    Keywords: Choristoneura rosaceana ; Pandemis limitata ; Tortricidae ; leafrollers ; communication disruption ; sex pheromone ; pheromone antagonist
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In British Columbia, trapping and wind-tunnel studies demonstrated that (Z)-9-tetradecenyl acetate (Z9–14:OAc), a minor component of the sex pheromone for Pandemis limitata, acted as a pheromone antagonist to a sympatric species, Choristoneura rosaceana. Addition of 〉1% Z9–14:OAc to the four-component C. rosaceana pheromone in a wind tunnel resulted in significant reductions in the proportion of male C. rosaceana that wing fanned, locked on to the plume in flight, oriented upwind, and made source contact, compared to the responses to the pheromone alone. Disruption of pheromone communication was tested in 33.3 × 33.3-m plots, at a release rate of 10 mg/ha/hr using Conrel fiber dispensers. Z9–14:OAc applied alone did not disrupt orientation to virgin-female-baited traps for either C. rosaceana or P. limitata. A 1:1 mixture of Z9–14:OAc and the four-component C. rosaceana pheromone was as effective as the pheromone alone at disrupting orientation of C. rosaceana males to virgin-female-baited traps, demonstrating that disruption apparently did not occur through false-trail following. The 1:1 mixture of Z9–14:OAc and the C. rosaceana pheromone also reduced catches of P. limitata males in virgin-female-baited traps, but not significantly more than the 83% disruption caused by the pheromone alone. Therefore, the C. rosaceana pheromone could be used alone or with Z9–14:OAc to disrupt communication and, presumably, mating in both leafrollers simultaneously.
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    URL: http://dx.doi.org/10.1023/A:1020997619135
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    Sex Pheromone of Nuttall's Sheep Moth, Hemileuca nuttalli, from the Eastern Sierra Nevada Mountains of California (1999)
    Springer
    Journal of chemical ecology 25 (1999), S. 711-726 
    Details
    ISSN: 1573-1561
    Keywords: Hemileuca nuttalli ; Hemileuca eglanterina ; E10,Z12-hexa-decadienyl acetate ; E10,Z12-hexadecadienyl acetate ; E10,Z12-hexadecadienol ; E10,Z12-hexadecadienal ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex attractant pheromone blend of Hemileuca nuttalli (Lepidoptera: Saturniidae) from the eastern slope of the Sierra Nevada Mountains in California was determined to be a combination of E10,Z12-hexadeca-10,12-dien-1-yl acetate (E10,Z12–16:Ac) and E10,E12-hexadeca-10,12-dien-1-yl acetate (E10,E12–16:Ac). Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:48, although the ratio was not critical in field trials. Blends of synthetic E10,Z12–16:Ac and E10,E12–16:Ac in 100:50, 50:100, and 100:100 ratios attracted equal numbers of male moths. Field trials also indicated that E10,Z12–hexadeca-10,12-dien-1-ol (E10,Z12–16:OH) and E10,Z12-hexadeca-10,12-dienal (E10,Z12–16:Ald) were antagonistic at rates of 3.3% and 10%, respectively, of the E10,Z12–16:Ac, despite being found in female moth extracts. E10,E12–16:Ac, E10,Z12–16:OH, and E10,Z12–16:Ald all appear to have roles in maintenance of reproductive isolation between H. nuttalli and H. eglanterina.
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    Rosefuran: The Sex Pheromone of an Acarid Mite, Caloglyphus Sp. (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 1771-1779 
    Details
    ISSN: 1573-1561
    Keywords: Mite ; Acaridae ; sex pheromone ; rosefuran ; Caloglyphus sp
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Rosefuran was identified as a female sex pheromone from an unnamed species of acarid mite, Caloglyphus sp., whose phoretic hypopi had been collected from the elongated yellowish chafer, Heptophylla picea. Behavior of sexually excited males was demonstrated by exposing them to doses of 1–100 ng of synthetic rosefuran. The pheromone was present in females and also in males and was detected in trace amounts in nymphal stages. Pheromone concentrations were estimated to be 87 ± 14.2 ng per female and 10.4 ± 2.5 ng per male. The quantitative difference between sexes may allow males to discriminate females for purposes of mating.
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    Geographic Variation in Sex Pheromone of Asian Corn Borer, Ostrinia furnacalis, in Japan (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 2079-2088 
    Details
    ISSN: 1573-1561
    Keywords: Ostrinia furnacalis ; sex pheromone ; (E)-12-tetradecenyl acetate ; (Z)-12-tetradecenyl acetate ; field trap experiment ; geographic variation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Geographic variation in the sex pheromone of the Asian corn borer, Ostrinia furnacalis (Guenée), was surveyed in populations sampled at four locations ranging from 39.7°N to 32.9°N in Japan. The sex pheromone of the three northern populations was composed of (E)- and (Z)-12-tetradecenyl acetates with a mean E proportion of 36–39%. The southernmost population (Nishigoshi) had the same components but with a significantly higher E composition of 44%. The frequency distribution of the E ratio in the Nishigoshi population exhibited a small peak near 38% and a major peak near 46%. A family-wise analysis of the sex pheromone of this population confirmed that there were two distinct phenotypes regarding the E ratio. An “≍46% E strain” inhabits southern parts of Japan, in addition to an “≍38% E strain,” which seems to be predominant in other regions of Japan.
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  • 27
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    Field Tests of Synthetic Sex Pheromone of the Apple Leafminer Moth, Phyllonorycter ringoniella (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 1939-1947 
    Details
    ISSN: 1573-1561
    Keywords: Phyllonorycter ringoniella ; apple leafminer ; sex pheromone ; (Z)-10-tetradecenyl acetate ; (E,Z)-4,10-tetradecadienyl acetate ; field trapping ; geographical variation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The apple leafminer moth, Phyllonorycter ringoniella, is becoming a more serious insect pest on apple trees with four to five generations a year in Korea. In order to devise a forecasting method for more accurate estimation of their numbers and development timing, the sex attractant was studied. Various ratios, from 10:0 to 0:10, of the two components, (Z)-10-tetradecenyl acetate (Z10–14:Ac) and (E,Z)-4,10-tetradecadienyl acetate (E4,Z10–14:Ac), identified from the sex pheromone gland (Jung and Boo, 1997), were tested for attractivity in terms of behavioral response (taxis, approach, and landing) against P. ringoniella males in a wind tunnel. The lure with Z10–14:Ac/E4,Z10–14:Ac in a ratio of 4:6 elicited the highest response in two (taxis and approach) measurement categories. For eliciting landing behavior, the two blends of 5:5 and 4:6 were best. The single component, Z10–14:Ac, elicited taxis behavior, but a combination of two chemicals was needed for eliciting all three behaviors. In the field, male attraction to various lure mixtures in Pherocon IC traps was usually greater than attraction to virgin females. The best field activity was in the lure baited with a 4:6 ratio of Z10–14:Ac and E4,Z10–14:Ac. Similar results were obtained from tests conducted in a net house. This optimum ratio for attracting P. ringoniella males in Korea is different from those reported in Japan (10:3) or China (7:3 to 6:4). The isomer E10–14:Ac neither improved nor depressed the number of catches when added at up to 10% of the total mixture to lures of the two components in the 4:6 ratio. The attractivity of the lures increased with higher amounts of the pheromones, up to 10 μg in the wind-tunnel experiment and 5 mg in the apple orchard. The number of males captured was not significantly different among traps installed at 0.3, 1.5, or 2 m above the ground, or among wing, delta, or water traps. A rubber septum dispenser impregnated with 1 mg of the 4:6 mixture maintained its field attractivity for up to eight weeks.
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    Sex Pheromone of Apple Blotch Leafminer, Phyllonorycter crataegella, and Its Effect on P. mespilella Pheromone Communication (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 2059-2078 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Gracillariidae ; Phyllonorycter crataegella ; Phyllonorycter mespilella ; sex pheromone ; (Z)-10,(Z)-12-tetradecadienyl acetate ; (E)-10,(E)-12-tetradecadienyl acetate ; (E)-4,(E)-10-dodecadienyl acetate ; interspecific effects
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z)-10,(Z)-12-Tetradecadienyl acetate (Z10,Z12–14:OAc) and (E)-10,(E)-12-tetradecadienyl acetate (E10,E12–14:OAc) are sex pheromone components of the apple blotch leafminer (ABLM), Phyllonorycter crataegella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses, retention index calculations of EAD-active compounds, and by comparative GC-EAD analyses of female ABLM-produced and authentic (synthetic) compounds. In field experiments in apple Malus domestica orchards in Connecticut, Z10,Z12–14:OAc alone attracted ABLM males. Addition of E10,E12–14:OAc to Z10,Z12–14:OAc at 0.1:10 or 1:10 ratios enhanced attractiveness of the lure. Geometrical isomers Z10,E12- or E10,Z12–14:OAc at equivalent ratios were behaviorally benign and slightly inhibitory, respectively. In field experiments in British Columbia, Z10,Z12–14:OAc plus E10,E12–14:OAc did not attract Phyllonorycter moths, supporting the contention that ABLM is not present in the fruit growing regions of British Columbia. Z10,Z12–14:OAc added to P. mespilella pheromone, (E)-4,(E)-10-dodecadienyl acetate, strongly inhibited response by P. mespilella males. Recognition of the ABLM pheromone blend by allopatric P. mespilella males suggests a phylogenetic relationship and previous sympatry of these two Phyllonorycter spp. If pheromonal attraction of ABLM males were reciprocally inhibited by P. mespilella pheromone, a generic Phyllonorycter pheromone blend could be tested for pheromone-based mating disruption of the apple leaf-mining Phyllonorycter guild in North America.
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    Sex Pheromone Components of Pitch Pine Looper, Lambdina pellucidaria (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 491-500 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Lambdina athasaria ; Lambdina fiscellaria ; Lambdina pellucidaria ; sex pheromone ; synergism ; 7,11-dimethyl-heptadecane ; 5,11-dimethylheptadecane ; 7-methylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two methylated hydrocarbons, 7-methylheptadecane (7) and 7,11-dimethylheptadecane (7,11), are sex pheromone components of female pitch pine looper (PPL), Lambdina pellucidaria. Compounds extracted from the pheromone glands of female moths were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD) and coupled GC–mass spectrometry (GC-MS) in selected ion monitoring mode. In field-trapping experiments, 7 and 7,11 in combination, but not singly, attracted numerous male moths. 5,11-Dimethylheptadecane (5,11) was detected by GC-EAD in female PPL pheromone gland extract, but did not significantly increase attraction of PPL males to 7 plus 7,11. Although 7 was 〉 10 times more abundant than 7,11 in pheromone gland extracts, traps baited with synthetic 7 plus 7,11 at a blend ratio of 1:1, rather than 1:0.1 or 1:0.01, captured the most PPL males. The chemical communication of PPL and spring hemlock looper (SHL), Lambdina athasaria, is strikingly similar. Both species employ 7 plus 7,11 as sex pheromone. Restriction of SHL to forests with eastern hemlock or balsam fir and PPL to forests with pitch or other hard pines contributes to their reproductive isolation. PPL and SHL may also use different optical isomers of enantiomeric 7 and stereoisomeric 7,11 to maintain specificity of their chemical communication.
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    Chemical and Behavioral Evidence for a Third Pheromone Component in a North American Population of the Black Cutworm Moth, Agrotis ipsilon (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 999-1011 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Feltia jaculifera ; Agrotis ipsilon ; sex pheromone ; wind tunnel ; pheromone traps ; male attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone of Agrotis ipsilon had been previously identified as a blend of (Z)-7-dodecenyl acetate (Z7–12:Ac) and (Z)-9-tetradecenyl acetate (Z9–14:Ac). A synthetic blend of Z7–12:Ac and Z9–14:Ac (30 μg:10 μg) is effective in attracting males in the field. In several countries, addition of (Z)-11-hexadecenyl acetate (Z11–16:Ac) to the previously identified blend increases male captures, but this had not been demonstrated in North America. We found Z11–16:Ac, in addition to Z7–12:Ac and Z9–14:Ac, from pheromone gland extracts of females from North America. The mean ratio of Z7–12:Ac, Z9–14:Ac, and Z11–16:Ac produced by individual females was 70.5:14.2:15.3, respectively. In Kentucky, addition of Z11–16:Ac (60 μg) to a two-component blend of Z7–12:Ac and Z9–14:Ac significantly increased the trap capture rate in the field. Traps baited with this three-component blend were 3.3 times (1995) and 4.6 times (1996) more effective in capturing male A. ipsilon than the two-component blend. This improved effectiveness resulted in detection of A. ipsilon in 60% more of the sampling periods in the two years. In the wind tunnel, males flew upwind and contacted a rubber septum loaded with a three-component blend including Z11–16:Ac significantly more frequently than they did to any two-component blend. These results demonstrate that Z11–16:Ac is a pheromone component in this North American population of A. ipsilon.
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    Responses of Tea Tussock Moth, Euproctis pseudoconspersa, to Its Pheromone, (R)-10,14-Dimethylpentadecyl Isobutyrate, and to the S-Enantiomer of Its Pheromone (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 1347-1353 
    Details
    ISSN: 1573-1561
    Keywords: Euproctis pseudoconspersa ; 10,14-dimethylpentadecyl isobutyrate ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field trials were conducted with each synthetic enantiomer (〉98% ee) and blends of the two synthetic enantiomers of the female-produced sex pheromone (10,14-dimethylpentadecyl isobutyrate) of the tea tussock moth, Euproctis pseudoconspersa. Male moths were attracted to each enantiomer alone and to various blends of them. Short syntheses of both enantiomers of the pheromone from commercially available (R)- and (S)-citronellyl bromide and a method of checking the enantiomeric purity of the citronellyl bromide enantiomers are described.
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    Attraction of Female and Male Bactrocera papayae to Conspecific Males Fed with Methyl Eugenol and Attraction of Females to Male Sex Pheromone Components (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 753-764 
    Details
    ISSN: 1573-1561
    Keywords: Bactocera dorsalis complex ; Bactrocera papayae ; sex pheromone ; coniferyl alcohol ; 2-allyl-4,5-dimethoxyphenol ; 3,4-dimethoxycinnamyl alcohol ; N-(3-methylbutyl) acetamide ; methyl eugenol ; wind tunnel ; mating competitiveness
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The attraction of female and male Bactrocera papayae to conspecific males fed with methyl eugenol (ME) and female attraction to male synthetic sex pheromone, trans-coniferyl alcohol (CF), were evaluated in a wind tunnel. Earlier and greater attraction were exhibited by both females and males to ME-fed than to non-ME-fed males as dusk approaches. Males increased their precopulatory behavior (i.e., wing fanning and mounting) during the period of higher attractancy. These data confirm that the consumption of ME enhances the mating competitiveness of males and suggest that ME also functions as a precursor to the male sex and aggregation pheromones. Three phenylpropanoid compounds biosynthesized from ME, coniferyl alcohol, 2-allyl-4,5-dimethoxyphenol, and 3,4-dimethoxycinnamyl alcohol, were detected in male rectal gland along with an endogenous rectal compound, N-(3-methylbutyl) acetamide. When offered singly to the females, coniferyl alcohol was found to be most attractive.
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    Sex Pheromone of Female Vine Bud Moth, Theresimima ampellophaga Comprises (2S)-Butyl (7Z)-Tetradecenoate (1998)
    Springer
    Journal of chemical ecology 24 (1998), S. 1141-1151 
    Details
    ISSN: 1573-1561
    Keywords: Theresimima ampellophaga ; Zygaenidae ; Lepidoptera ; sex pheromone ; (2S)-butyl (7Z)-tetradecenoate ; electroantennogram
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone of the vine bud moth, Theresimima ampellophaga, released at the 3rd–5th abdominal tergites, was identified by coupled GC-EAG, GC-MS, and synthesis as (2S)-butyl (7Z)-tetradecenoate. For the first time, full stereochemistry is unambiguously defined for the sex pheromone of a member of the Zygaenidae. The synthetic compound caught significant numbers of males in field-trapping experiments.
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    URL: http://dx.doi.org/10.1023/A:1022438717287
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    (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae) (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 19-34 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lymantriidae ; Orgyia pseudotsugata ; tussock moth ; (Z)6,(Z)9-heneicosadien-11-one ; (Z)6,(E)8-heneicosadien-11-one ; (Z)6,(Z)9-heneicosadien-11-one ; sex pheromone ; synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic–electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC–mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.
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    Sex Pheromone Stereochemistry and Purity Affect Field Catches of Male Aphids (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2547-2554 
    Details
    ISSN: 1573-1561
    Keywords: Aphid ; sex pheromone ; stereochemistry ; (4aS,7S,7aR)-nepetalactone ; (4aS,7S,7aR)-nepetalactols
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male blackberry-cereal aphids, Sitobion fragariae (Walker), were caught in the ield by water traps releasing synthetic (4aS, 7S, 7aR)-nepetalactone, the major sex pheromone component. The presence of the enantiomer (4aR,7R,7aS)-nepetalactone reduced catches and a plant-extracted (4aS,7S,7aR)-nepetalactone was less effective than the 99% (7S)-lactone. A more extensive trial with the bird cherry-oat aphid, Rhopalosiphum padi, involving the pheromone comprising the stereochemically related (4aS,7S,7aR)-nepetalactol showed a similar trend. The (7R)-isomer caught fewer males than the (7S)-isomer, but in this case the addition of high-purity (7S)-lactol to make a 50% blend caught as many males as pure (7S)-lactol. With plant-derived lactol, further purification did not significantly increase the catch. It is suggested that trace compounds associated with reduced enantiomeric purity in terms of the (7S)-configuration or from plant sources reduce activity of the sex pheromone components. Male damson-hop aphids, Phorodon humuli (Schrank), were also caught in the synthetic lactol traps, and it is suggested that this is due to traces of the (4aR,7S,7aS)-nepetalactols, which comprise the sex pheromone for this species. The significance for aphid chemical ecology studies and pest control strategies is discussed.
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    URL: http://dx.doi.org/10.1023/B:JOEC.0000006665.05409.97
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    Identification of Sex Pheromone of Adzuki Bean Borer,Ostrinia scapulalis (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2791-2802 
    Details
    ISSN: 1573-1561
    Keywords: Ostrinia scapulalis ; sex pheromone ; (Z)-11-tetradecenyl acetate ; (E)-11-tetradecenyl acetate ; GC-EAD ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract By means of gas chromatography with electroantennographic detection (GC-EAD), gas chromatography–mass spectrometry (GC-MS), and a series of bioassays, (Z)-11-tetradecenyl acetate (Z11–14:OAc) and (E)-11-tetradecenyl acetate (E11–14:OAc) at a ratio of 100:3 were identified as the female sex pheromone of the adzuki bean borer,Ostrinia scapulalis. The average amounts ofZ11–14: OAc andE11–14:OAc in a single sex pheromone gland were 6.6 ± 2.4 ng and 0.2 ± 0.1 ng, respectively. In a wind-tunnel bioassay, the binary blend ofZ11- andE11–14:OAc elicited almost the same male behavioral responses as did virgin females and sex pheromone gland extract. In field trapping experiments, rubber septa impregnated with the binary blend (50 μg/septum) attracted more males than virgin females. The sex pheromone ofO. scapulalis thus turned out to be similar to that of theZ-type European corn borer,O. nubilalis, in both components and their ratio.
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    Identification of Sex Pheromones of Leucania anteoclara Sm. and Leucania commoides Gn. (Lepidoptera: Noctuidae: Hadeninae) (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 473-485 
    Details
    ISSN: 1573-1561
    Keywords: Leucania anteoclara ; Leucania commoides ; Lepidoptera ; Noctuidae ; sex pheromone ; (Z)-11-hexadecenyl acetate ; (Z)-9-tetradecenyl acetate ; (Z)-11-hexadecenyl aldehyde ; (Z)-11-hexadecenyl alcohol ; seasonal flight period ; abundance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone components of two species of Leucania that occur sympatrically in western Canada were identified in abdomen-tip extracts from calling female moths. (Z)-11-hexadecenyl acetate was the main component and (Z)-9-tetradecenyl acetate the second component in both species. The third component necessary for specific attractancy was (Z)-11-hexadecenyl aldehyde for L. anteoclara and (Z)-11-hexadecenyl alcohol for L. commoides. The third component for each species was an attractant inhibitor when added as a fourth component to the attractant blend for the reciprocal species. The most effective synthetic blend for the attraction of males in the field was Z9–14:Ac/Z11–16:Ac/Z11–16:Ald in a ratio of 1:10:4 for L. anteoclara and Z9–14:Ac/Z11–16:Ac/Z11–16:OH in a ratio of 5:4:1 for L. commoides.
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    Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1119-1130 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lyonetiidae ; Lyonetia prunifoliella ; Perileucoptera coffeella ; Lyonetia clerkella ; Leucoptera malifoliella ; sex pheromone ; synergism ; 10,14-dimethyloctadec-1-ene ; 5,9-dimethyloctadecane ; 5,9-dimethylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three methylated hydrocarbons, 10,14-dimethyloctadec-1-ene (10Me14Me-1-ene-18Hy = 5Me9Me-17-ene-18Hy), 5,9-dimethyloctadecane (5Me9Me-18Hy), and 5,9-dimethylheptadecane (5Me9Me-17Hy), are synergistic sex pheromone components of the leafminer Lyonetia prunifoliella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD), and one compound, 10Me14Me-1-ene-18Hy, also by coupled GC–mass spectrometry. In field trapping experiments, 10Me14Me-1-ene-18Hy, 5Me9Me-18Hy, and 5Me9Me-17Hy singly were unattractive to males but in ternary combination attracted numerous male moths. Attractiveness of the three-component blend significantly exceeded that of two-component blends. No attraction of males to pheromone lures without 10Me14Me-1-ene-18Hy indicates that this compound is essential for pheromone communication of L. prunifoliella. Common C-5 and C-9 methyl branches in lyonetiid pheromone hydrocarbons suggest a common biosynthetic pathway; the presence of 5Me9Me-17Hy and 5Me9Me-18Hy in pheromone blends of L. prunifoliella and Leucoptera malifoliella provides evidence for phylogeny of lyonetiid chemical communication. Determination of the stereoisomeric composition is required to completely describe the pheromone blend of L. prunifoliella and to support the hypothesis of phylogenetically related sex pheromones.
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    Cuticular Hydrocarbons of Glossina, III: Subgenera Glossina and Nemorhina (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1291-1320 
    Details
    ISSN: 1573-1561
    Keywords: Tsetse fly ; sex pheromone ; gas–liquid chromatography ; mass spectrometry ; methylalkanes ; patterns ; Diptera ; hydrocarbons
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cuticular methyL-branched alkanes of tsetse flies of the subgenera Glossina (sensu stricto, formerly morsitans) and Nemorhina (formerly palpalis) were identified and quantified by capillary gas–liquid chromatography (GC) and gas chromatography–mass spectrometry (GC-MS). Males of Glossina (Nemorhina) are differentiated from G. (Glossina) by dominant 27-, 28-, and/or 29-carbon backbone trimethylalkanes with the methyl positions at 3,7,11-, 4,8,12-, and 3,7,11-, respectively. All females contain major quantities of long-chain internally branched di- and/or trimethylalkanes that were previously implicated as mediators of sexual behavior in males. Taxa within these two subgroups that are closely related and/or conspecific, based upon conventional morphological and ecological criteria, exhibit similar GC patterns and similar internally branched di- and trimethylalkane isomers in females. Examination of these potentially stimulatory methylalkanes may provide reasons for the reproductive isolation of closely related species from each other.
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    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.
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    Optimization of Pheromone Dispensers for Diamondback Moth Plutella xylostella (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2145-2159 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Plutellidae ; (Z)-11-hexadecenyl acetate ; (Z)-11-hexadecenal ; Plutella xylostella L. ; diamondback moth ; sex pheromone ; dispenser ; cabbage ; pheromone evaporation rate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract We have investigated the effects of pheromone dispenser design, pheromone release rate, and the products of Z11–16:Ald decomposition on the attractiveness of the pheromone blend (Z)-11-hexadecenyl acetate, (Z)-11-hexadecenal, and (Z)-11-hexadecen-1-ol) in traps to Plutella xylostella males. Rubber minidispensers (K-50) were shown to have an active exposure time of at least two months and in delta traps to be capable of monitoring a population of P. xylostella throughout the summer in Estonia. Pheromone release rates between 8 and 17 ng/hr are recommended for maximum trap catches. The attractive blend contained 15–35% of Z11–16:Ac. Decomposition products of Z11–16:Ald inhibited the activity of the pheromone blend when more than 50% of the aldehyde had decomposed.
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    Essential Amino Acid Methyl Esters: Major Sex Pheromone Components of the Cranberry White Grub, Phyllophaga anxia (Coleoptera: Scarabaeidae) (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 231-245 
    Details
    ISSN: 1573-1561
    Keywords: Phyllophaga anxia ; Coleoptera ; Scarabaeidae ; cranberry white grub ; sex pheromone ; chirality ; L-valine methyl ester ; L-isoleucine methyl ester ; electroantennographic detection ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chiral capillary gas chromatographic–electroantennographic detection (GC-EAD) analysis indicates that L-valine and L-isoleucine methyl esters are the major sex pheromone components released by females of the cranberry white grub, Phyllophaga anxia (LeConte). The GC retention times and GC-mass spectrometry of the two natural compounds were identical to those of authentic standards. Of five reproducible GC-EAD active components revealed with female volatiles, the L-valine and L-isoleucine methyl esters elicited the strongest male antennal responses. The ratio of L-valine and L-isoleucine methyl esters was determined to be 3:1 by analysis of pheromone gland extracts. Chirality was shown to be critical by GC-EAD, since only the L-form of these amino acid methyl esters elicited an EAD response. In field experiments conducted in Massachusetts, a synthetic 3:1 blend of L-valine and L-isoleucine methyl esters on a rubber septum was attractive to P. anxia males.
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    Resolution of Pheromonal Epoxydienes by Chiral HPLC, Stereochemistry of Separated Enantiomers, and Their Field Evaluation (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1403-1417 
    Details
    ISSN: 1573-1561
    Keywords: Chiral HPLC ; sex pheromone ; Lepidoptera ; Geometridae ; epoxydiene ; stereochemistry ; Mosher's method
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Resolution of insect pheromonal cis-epoxydiene racemates derived from (Z,Z,Z)-3,6,9-trienes with a C18–C23 chain was examined utilizing chiral HPLC columns, and the result showed that a Chiralpak AS column was suitable to separate enantiomers of the 3,4-epoxides, and a Chiralpak AD column was indispensable for the resolution of the racemic 6,7- and 9,10-epoxides. The absolute configuration of the enantiomers of the 3,4- and 9,10-epoxides separated by HPLC was studied after methanolysis of their epoxy rings. Examination of the 1H NMR data from esters of the methoxyalcohols produced by a modified Mosher's method with (S)- and (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid indicated that the dextrorotatory parent epoxides with a shorter R t were 3S,4R and 9S,10R isomers and the levorotatory enantiomers having a longer R t possessed 3R,4S and 9R,10S configuration. Field tests with both enantiomers of (Z,Z)-6,9-cis-3,4-epoxynonadecadiene separated by HPLC with the chiral column revealed new specific attraction of geometrid forest defoliators, Pachyerannis obliquaria, to the 3R,4S isomer and Zethenia albonotaria nesiotis to the 3S,4R isomer.
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    Sex Pheromone of the Mirid Bug Phytocoris relativus (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1743-1754 
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    ISSN: 1573-1561
    Keywords: Phytocoris relativus ; Miridae ; sex pheromone ; pistachio ; monitoring ; hexyl acetate ; (E)-2-octenyl butyrate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex attractant pheromone produced by adult females of the mirid bug Phytocoris retativus has been identified as a 2:1 blend of hexyl acetate with (E)-2-octenyl butyrate. The pheromone is stage-, sex-, and species-specific, attracting only adult male P. relativus. Hexyl acetate was identified in aeration extracts from both sexes, while (E)-2-octenyl butyrate was produced only by females. Both males and females also produced hexyl butyrate and octyl acetate, while only females produced (E)-2-hexenyl and octenyl acetates, and (Z)-3-octenyl acetate. The function(s) of these chemicals were not determined. Attraction of males increased with dose, with doses of 0.1 to 33 mg loaded on grey rubber septa. Attractiveness of rubber septum lures decreased quickly with age due to the volatility of the two pheromone components.
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    Individual Variation and Repeatability of Sex Pheromone Emission of Female Turnip Moths Agrotis segetum (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1833-1850 
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    ISSN: 1573-1561
    Keywords: Agrotis segetum ; Lepidoptera ; (Z)-5-decenyl acetate ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecenyl acetate ; sex pheromone ; individual variation ; repeatability ; effluvia entrainment
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Individual variation of the female sex pheromone signal in Agrotis segetum was determined by gas chromatographic analysis. The individuals varied extensively, both in absolute and relative amounts of the three major pheromone components; Z5–10:OAc, Z7–12:OAc and Z9–14:OAc. Within individuals there was a strong correspondence between the sex pheromone gland content and the signal actually emitted. Both pheromone amounts and proportions of components were correlated with effluvia and extracts; with coefficients of 0.55 for total amounts and 0.66 for proportions. In addition, the repeatability of emitted pheromone components by individual females over three calling periods was high, with correlation coefficients between 0.43 and 0.72. Variation among individual females, however, was observed. There were no significant differences between wild-collected and laboratory-reared females in average ratios of the major pheromone components in pheromone gland extracts, only in total amounts. The biological significance of the inter-individual variation among females is discussed in the context of population dynamics and sexual selection.
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    Identification of Sex Pheromone Components of Nettle Caterpillar, Setothosea asigna (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2187-2196 
    Details
    ISSN: 1573-1561
    Keywords: Setothosea asigna ; nettle caterpillar ; Limacodidae ; Lepidoptera ; sex pheromone ; (E)-9-dodecenal ; (E)-9,11-dodecadienal ; oil palm ; Elaeis guineensis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic–electroantennographic detection (GC-EAD) analyses of female nettle caterpillar, Setothosea asigna, pheromone gland extracts revealed seven antennally active compounds. Based on their retention indices on three fused silica columns (DB-5, DB-23, and DB-210), these compounds were hypothesized and, through comparative GC, GC-EAD and GC-mass spectrometry with authentic standards, confirmed to be Δ10-undecenal, dodecanal, (E)-9-dodecenal (E9–12:Ald), (Z)-9-dodecenal, (E)-9-dodecen-1-ol, (E)-9,11-dodecadienal (E9,11–12:Ald), and (E)-9,11-dodecadienol. E9–12:Ald and E9,11–12:Ald were most abundant in female S. asigna pheromone extracts. In field trapping experiments in Palembang, Indonesia, synthetic E9–12: Ald and E9,11–12:Ald at a 1:1 ratio, but not singly, attracted S. asigna males. Attractiveness of these two aldehydes could not be enhanced further through the addition of their corresponding alcohols and/or other aldehydic candidate pheromone components. Use of E9–12:Ald and E9,11–12:Ald for pheromone-based monitoring of S. asigna populations will require lure formulations that minimize pheromone degradation by ultraviolet radiation and atmospheric oxidation.
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    Disruption Mechanisms of Pheromone Communication in the European Grape Moth Lobesia botrana Den & Schiff. III. Sensory Adaptation and Habituation (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 83-95 
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    ISSN: 1573-1561
    Keywords: Lobesia botrana ; European grape moth ; sex pheromone ; mating disruption ; insect marking technique
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Disruption experiments were carried out under vineyard conditions and in the laboratory. Males from laboratory cultures were conditioned in an atmosphere permeated with pheromone (E7 Z9-12Ac), marked externally with fluorescent powder, and released in the middle of vine plots. They were then trapped in a series of traps baited with virgin females or dispensers loaded with various amounts of pheromone. Over 10,000 males were released in these experiments between 19 May and 22 July. Electroantennography tests were used for studying olfactory sensitivity in pheromone-permeated air by measuring the EAG responses of male antennae in constant pheromone air-flows. The conclusion is that both sensory adaptation and central nervous system habituation mechanisms acted simultaneously in air laden with pheromone, but they are probably not relevant when concentrations are of the same order of magnitude as those obtained under field conditions in which mating disruption methods are used for controlling the European grape moth.
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    Two Regional Strains of a Phoretic Egg Parasitoid, Telenomus euproctidis (Hymenoptera: Scelionidae), That Use Different Sex Pheromones of Two Allopatric Tussock Moth Species as Kairomones (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 153-161 
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    ISSN: 1573-1561
    Keywords: Telenomus euproctidis ; phoresy ; kairomone ; sex pheromone ; Euproctis taiwana ; Euproctis pseudoconspersa ; egg parasitoid ; tussock moth
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The egg parasitoid, Telenomus euproctidis Wilcox (Hymenoptera: Scelionidae), is phoretic on females of two allopatrically distributed tussock moths, Euproctis pseudoconspersa (Strand) and Euproctis taiwana (Shiraki) (Lepidoptera: Lymantriidae). Crossing experiments between the two regional parasitoid strains indicated no evidence for their reproductive isolation. More wasps were found on the locally occurring host, E. pseudoconspersa, than on E. taiwana, when virgin females of the two moth species were exposed concurrently in the field for 24 hr in Ibaraki Japan. In Ibaraki, many wasps were caught in traps baited with the synthetic sex pheromone of E. pseudoconspersa, 10,14-dimethylpentadecyl isobutyrate (10Me14Me-15:iBu), but none with that of E. taiwana, (Z)-16-methyl-9-heptadecenyl isobutyrate (16Me-Z9-17:iBu) or blank traps. In Okinawa, Japan, more wasps were found on E. taiwana than on E. pseudoconspersa, and many wasps were caught in traps baited with 16Me-Z9-17:iBu, but only a few with 10Me14Me-15:iBu, and none with blank traps. These results suggest that local wasp strains discriminate between the two sex pheromones, and they strongly prefer the sex pheromone of the moth occurring at their location.
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    Sex Pheromone of the French Black Cutworm Moth, Agrotis ipsilon (Lepidoptera: Noctuidae): Identification and Regulation of a Multicomponent Blend (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 211-230 
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    ISSN: 1573-1561
    Keywords: Agrotis ipsilon ; sex pheromone ; gas chromatography/high-resolution mass spectrometry ; pheromone biosynthesis activating neuropeptide ; cis-7-dodecenyl acetate ; cis-9-tetradecenyl acetate ; cis-11-hexadecenyl acetate ; polymorphism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone blend of a European strain of the black cutworm moth, Agrotis ipsilon (Hufnagel), was investigated. Chemical analyses of pheromone gland extracts from 4- to 8-day-old females showed that individual isolated glands contained only very small amounts of pheromone. High-resolution gas chromatography combined with mass spectrometry (GC–MS) analyses showed the presence of cis-7-dodecenyl acetate (Z7-12:Ac), cis-9-tetradecenyl acetate (Z9-14:Ac), cis-11-tetradecenyl acetate (Z11-14:Ac), cis-11-hexadecenyl acetate (Z11-16:Ac), and cis-11-hexadecenol (Z11-16:OH) in biologically active pheromone gland extracts. Removing 27-12: Ac, Z9-14:Ac, or Z11-16:Ac from the complete gland extract by GC trapping techniques strongly reduced the attractiveness of the pheromone blend tested in a wind tunnel. Lack of cis-5-decenyl acetate (Z5-10:Ac) or Z11-16:OH did not affect the blend attractiveness. Chemical and behavioral analyses showed that pheromone components are produced during photophase, at least 2 hr before lights off. Quantitative data showed that decapitation inhibited the production of Z7-12:Ac, Z9-14:Ac, Z11-14:Ac, Z11-16:Ac, and Z11-16:OH, but production in decapitated females was stimulated in response to injection of synthetic Heliothis zea PBAN (pheromone biosynthesis activating neuropeptide) or A. ipsilon brain–subesophageal (Br-SEG) homogenates. Moreover, upon injecting BR-SEG homogenates, other minor components were detected, which were tentatively identified as cis-8-dodecenyl actetate (Z8-12:Ac) and Z5-10:Ac. Our study demonstrated that Z11-l6:Ac is one of the main active components produced by the pheromone gland of this European population of A. ipsilon, in addition to Z7-12:Ac/Z9-14:Ac, which were investigated in a previous behavioral analysis. All these data strongly suggest that some polymorphism is present in pheromone communication in different strains of A. ipsilon.
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    Electrophysiological and Behavioral Evidence for a Sex Pheromone in the Wasp Bephratelloides pomorum (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1281-1289 
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    ISSN: 1573-1561
    Keywords: Bephratelloides pomorum ; B. cubensis ; Annona muricata ; portable EAG ; sex pheromone ; Hymenoptera ; Eurytomidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field experiments showed that males of the seed-feeding, Neotropical wasp Bephratelloides pomorum are strongly attracted to females. That this attraction was semiochemically mediated was demonstrated by both the response of male antennae to the whole-body extract of females and by behavioral bioassays. In the field, males were captured in traps baited with female thoraces, but not with other body parts (abdomen and head). Volatiles collected from the headspace of female wasps or whole-body extracts, concentrated and transferred to cotton plugs, elicited a full sequence of sexual behavior in male wasps. The attraction of males to female-baited traps showed a peak of activity at noon, but in indoor bioassays male responded to female extracts even at night.
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    Increase of Trap Catches by a Combination of Male Sex Pheromones and Floral Attractant in Longhorn Beetle,Anaglyptus subfasciatus (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 1635-1640 
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    ISSN: 1573-1561
    Keywords: Anaglyptus subfasciatus ; Coleoptera ; Cerambycidae ; sex pheromone ; methyl phenylacetate ; trap catches ; synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A combination of the synthetic sex pheromone [a 125:1 blend of (R)-3-hydroxy-2-hexanone and (R)-3-hydroxy-2-octanone] with methyl phenylacetate captured significantly moreAnaglyptus subfasciatus Pic females than either the sex pheromone or methyl phenylacetate did alone.
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    Efficacy of nonpheromone communication disruptants of codling moth (Cydia pomonella): Effect of pheromone isomers and of distance between calling females and dispensers (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 415-423 
    Details
    ISSN: 1573-1561
    Keywords: Codling moth ; Cydia pomonella ; sex pheromone ; codlemone ; (E,E)-8,10-dodecadien-1-ol ; sex pheromone isomers ; 8,10-dodecadien-1-ol isomers ; (E,Z)-8,10-dodecadien-1-ol ; mating disruption ; communication disruption
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field tests comparing the ability of codlemone, (E,E)-8,10-dodecadien-1-ol, and isomers of codlemone to disrupt pheromonal communication of codling moth were carried out. In a pear orchard, four nonisomerizing, gray septa dispensers were placed in the upper canopy of each tree containing a trap baited with 10 virgin female codling moths. The dispensers were at trap height and 70 cm from the edge of each trap. Trap catches of released male codling moths in three test areas were compared simultaneously when trees in each of the test areas contained unbaited dispensers, dispensers with 1 mg of codlemone containing 1% isomers, and dispensers with 1 mg of a test communication disruptant. When the test disruptant was an equilibrium mixture of codlemone and its isomers (61% codlemone, 39% isomers), the percent communication disruption was 86.8% compared to 68.7% for codlemone (P 〈 0.001). When the disruptant was (E,Z)-8,10-dodecadien-1-ol (94%EZ, 3%EE), the percentage disruption was 86.4% compared to 62.7% for codlemone (P 〈 0.002). These results show that the previously reported superior disruptant potency (relative to codlemone) of compositions containing codlemone with a high percentage of isomers was not a result of the proximity of the dispensers to the traps. The percent disruption of compositions of codlemone with 10 and 20% isomers was also determined. A plot of percentage disruption versus logarithm of percentage of nonpheromone isomers in the mixture from 1% to 97% gave a straight line withR 2=0.93.
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    Phoretic egg parasitoid,Telenomus euproctidis (Hymenoptera: Scelionidae), uses sex pheromone of tussock mothEuproctis taiwana (Lepidoptera: Lymantriidae) as a kairomone (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1079-1085 
    Details
    ISSN: 1573-1561
    Keywords: Telenomus euproctidis ; kairomone ; sex pheromone ; phoresy ; Euproctis taiwana
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The phoretic egg parasitoid,Telenomus euproctidis Wilcox (Hymenoptera: Scelionidae) was found more frequently on virgin than on mated female moths ofEuproctis taiwana (Shiraki) (Lepidoptera: Lymantriidae), when virgin and mated moths were exposed concurrently in the field for 24 hr. A synthetic component of the moth's sex pheromone. (Z)-16-methyl-9-heptadecenyl isobutyrate, attracted both the wasp,T. euproctidis, and maleE. taiwana. These findings suggest thatT. euproctidis uses the sex pheromone of the female moth,E. taiwana, as a kairomone to locate a host female moth and through her the host eggs.
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    Reproductive biology of the yellow-spotted longicorn beetle,Psacothea hilaris (pascoe) (Coleoptera: Cerambycidae). III. Identification of contact sex pheromone on female body surface (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 259-270 
    Details
    ISSN: 1573-1561
    Keywords: Cuticular hydrocarbon ; contact pheromone ; sex pheromone ; mating behavior ; Coleoptera ; Cerambycidae ; Psacothea hilaris ; (Z)-21-methyl-8-pentatriacontene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A major component of female contact sex pheromone of the yellow-spotted longicorn beetle,Psacothea hilaris (Pascoe), was isolated from the elytra and identified as (Z)-21-methyl-8-pentatriacontene. The synthetic compound released the typical mating behavior including holding, mounting, and abdominal bending in males, although its activity was considerably lower than the extract of female elytra when treated on a gelatin capsule as an artificial female model.
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    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.
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    Structure-activity relationship observations for the bagworm moth pheromone (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1315-1324 
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    ISSN: 1573-1561
    Keywords: SAR ; Psychidae ; Thyridopteryx ephemeraeformis ; bagworm moth ; sex pheromone ; (R)-2-pentyl decanoate ; Chem-X ; molecular modeling
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Structure-activity relationship (SAR) observations were made for the bagworm moth pheromone, (R)-2-pentyl decanoate, and a series of analogs with modifications in the alcohol portion of the molecule. Observed attractiveness of these analogs was related to molecular structure and their physical attributes using computational chemistry. Electrostatic potential and Van der Waals (VdW) electrostatic coded surface three-dimensional (3D) maps of the molecular mechanics (MM) minimized lowest energy conformation of the pheromone show that size, shape, charge distribution, and chirality of the molecule are related to attractiveness.
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    Sex pheromone ofStenoma cecropia Meyrick (Lepidoptera: Elachistidae) (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1103-1121 
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    ISSN: 1573-1561
    Keywords: Lepidoptera ; Elachistidae ; Stenoma cecropia ; sex pheromone ; identification ; electroantennography ; single sensillum recording ; field trapping (Z,E)-9,11-tetradecadienal ; (Z,E)-9,11,13-tetradecatrienal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z,E)-9,11-tetradecadienal (Z9,E11–14: Ald; 11%), (Z,E)-9,11,13-tetradecatrienal (Z9,E11, 13–14: Ald; 67%), (Z,E)-9,11-tetradecadienyl acetate (Z9,E11–14: Ac, 5.5%), and (Z,E)-9,11,13-tetradecatrienyl acetate (Z9,E11,13–14: Ac; 16.5%) were identified in the extracts of female pheromone glands ofStenoma cecropia (Lepidoptera: Elachistidae). From electroantennograms and single sensillum recordings, receptors toZ9,E11,13–14:Ald andZ9,E11–14: Ald were found on male antenna. Behavioral data were obtained from olfactometric tests in the laboratory and field trapping experiments in Colombia. It appeared that a blend ofZ9,E11,13–14:Ald (83%) andZ9,E11–14:Ald (17%) was attractive to males. These aldehydes are assumed to be components of the sex pheromone ofS. cecropia, whereas the acetates found in gland extracts might be precursors of the pheromone.
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    The pheromone of the eastern tent caterpillar,Malacosoma americanum (F.) (lepidoptera, Lasiocampidae) (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 2251-2261 
    Details
    ISSN: 1573-1561
    Keywords: Attractant ; reproductive isolation ; field trapping ; (E,Z)-5,7-dodecadienal ; (E,Z)-5,7-dodecadien-1-ol ; eastern tent caterpillar ; Malacosoma americanum ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The pheromone system of the eastern tent caterpillar,M. americanum, has been identified as a mixture of (E,Z)-5,7-dodecadienal and the corresponding alcohol. Field data on the attractiveness of the aldehyde alone were not consistent, but mixtures of aldehyde and alcohol in varying proportions were attractive to males. Addition of small amounts ofE,Z acetate toE,Z aldehyde had no effect on male response, but larger amounts reduced trap catch. Traps baited withZ,E, E,E, orZ,Z aldehydes were not more attractive than blank traps. Pherocon IC traps fortified with extra adhesive and baited with lures consisting of 500 µg (E,Z)-5,7-dodecadienal with either 250 or 100 µg of the corresponding alcohol trapped as many as 100 males/trap/night with means of 15–20. Lures prepared from purified (94%E,Z) aldehyde and alcohol were more attractive than those prepared from unpurified (58%E,Z) materials.
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    Disruption of male oriental fruit moth to calling females in a wind tunnel by different concentrations of synthetic pheromone (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1971-1986 
    Details
    ISSN: 1573-1561
    Keywords: Oriental fruit moth ; sex pheromone ; mating disruption ; windtunnel tests
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Disruption of male Oriental fruit moth orientation to calling females was studied in a wind tunnel by surrounding calling female moths with septa loaded with synthetic pheromone. At the lowest loadings, 0.01 and 0.1µg, which produced release rates well below those of calling females, some males flew to septa instead of the females. At loadings of 1 and 10µg, which produced release rates close to those of a calling female, more than half the males flew to septa instead of the females, but there was little evidence of habituation at any of these loadings. At higher loadings, 100 and 1000µg, upwind flight of males was arrested, and many males remained inactive, indicating habituation. Preexposure of the males for 3 hr to ambient pheromone concentrations in the tunnel had no significant effect on numbers of disrupted males. However, at the 1000-µg loading, most of the males that had been preexposed to the synthetic pheromone remained inactive. This may indicate a higher level of habituation than among males that had not been preexposed, most of which flew, although they subsequently showed flight arrestment. Levels of disruption were similar to those found for the spruce budworm in comparable experiments. In both species, less than 1% of the males were able to locate females when time-averaged concentrations of synthetic pheromone were above 20 ng/m3. However, levels of inactivity and flight arrestment were higher among male Oriental fruit moths than among male spruce budworms, which may explain why Oriental fruit moths are more susceptible to disruption than are spruce budworms.
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    URL: http://dx.doi.org/10.1007/BF02040089
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    Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 13-27 
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    ISSN: 1573-1561
    Keywords: Stigmella malella ; Stigmella crataegella ; Trifurcula (Glaucolepis) melanoptera ; Lepidoptera ; Nepticulidae ; sex pheromone ; (S)-(E)-6,8-nonadien-2-ol ; (S)-(Z)-6,8-nonadien-2-ol ; (R)-(E)-6,8-nonadien-2-ol ; (R)-(Z)-6,8-nonadien-2-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Short-chain unsaturated chiral methyl carbinols are identified as a new class of lepidopteran pheromone components. The natural female-produced pheromone of the banded apple pigmyStigmella malella (=Nepticula malella) (Stainton) (Lepidoptera: Nepticulidae) was identified to be a mixture of (S)-(E)-6,8-nonadien-2-ol and (S)-(Z)-6,8-nonadien-2-ol. For monitoring traps, a 10:3E:Z blend at 100–1000 µg is recommended. It is suggested that pheromones with similar structures may be specific to Nepticulidae and other related microlepidopteran families.
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    Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 29-43 
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    ISSN: 1573-1561
    Keywords: Eriocrania cicatricella ; Eriocrania sparrmannella ; Eriocraniidae ; Lepidoptera ; sex pheromone ; EAG ; GC-EAD ; mass spectrometry ; synthesis ; evolution ; (Z)-4-hepten-2-one ; (2R)-heptan-2-ol ; (2R)-(Z)-4-hepten-2-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts from different body parts of adult femaleEriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols withS-configuration was attractive to maleE. sparrmannella (Bosc), whereas no males ofE. cicatricella were found in these traps. The sex pheromone compounds inE. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.
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    Controlled-release pheromone dispenser for use in traps to monitor flight activity of false codling moth (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 355-363 
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    ISSN: 1573-1561
    Keywords: Cryptophlebia leucotreta ; controlled-release phermone dispenser ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field trials were conducted in the western Cape Province, South Africa, to develop a sex pheromone dispenser suitable for monitoring the flight activity of false codling moth. A controlled-release dispenser capable of releasing sex pheromone at a predetermined and constant release rate without replacement for more than seven months was produced.
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    URL: http://dx.doi.org/10.1007/BF02036723
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    Use of paired and single traps to assess perception and discrimination of sex pheromone mixtures in the field byTrichoplusia ni (Hübner) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 2057-2068 
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    ISSN: 1573-1561
    Keywords: Behavior ; perception ; discrimination ; trap ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Paired wind-oriented traps (WORT) and single traps were deployed simultaneously in the same field to investigate whether or not inferences about the central nervous system processes of discrimination and perception can be made from differences in moth captures. The stimulus levels deployed were those that typically may be found downwind of a calling virgin female cabbage looper,Trichoplusia ni (Hübner), so that inferences are relevant to natural stimulus intensities. Captures of male cabbage loopers in the WORT traps paralleled prior laboratory measures of pheromone mixture discrimination. The pattern of captures by the two trapping systems probably reflects perceptive and discriminative processing differences in the central nervous system. Captures in traps baited withZ7–12: Ac alone were equal to, or better than, captures in traps baited with three- and six-component mixtures that containedZ7–12: Ac.
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    Pheromones in red pine cone beetle,Conophthorus resinosae hopkins, and its synonym,C. banksianae McPherson (Coleoptera: Scolytidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 169-185 
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    ISSN: 1573-1561
    Keywords: Conophthorus resinosae ; Conophthorus banksianae ; cone beetle ; Scolytidae ; sex pheromone ; repellent ; pityol ; 2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran ; spiroacetal ; 7(E)-methyl-1,6-dioxaspiro[4.5]decane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Analyses of abdominal extracts and beetle-produced volatiles revealed that femaleConophthorus resinosae andC. banksianae produced optically pure (E)-(+)-pityol [(2R,5S)-(+)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran]. In field tests, traps baited with (E)-(±)- or (E)-(+)-pityol captured only males. Addition of host oils to traps baited with pityol did not significantly enhance the capture of males. Males of these former sibling species produced the spiroacetal (5S,7S)-(−)-7-methyl-1,6-dioxaspiro[4.5]decane with high optical purity (96%). Addition of the racemate or the optical isomers of the spiroacetal to traps baited with (E)-(±)-pityol almost completely inhibited the capture of males. It is hypothesized that to ensure their reproductive success, males produce the spiroacetal to repel rival males. Species specificity in pityol and the spiroacetal was not found betweenC. resinosae andC. banksianae, thus supporting their synonymy.
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    Production and release of (Z,E)-9,12-tetradecadienal by sex pheromone glands of females ofPlodia interpunctella (lepidoptera: pyralidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 787-799 
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    ISSN: 1573-1561
    Keywords: Plodia interpunctella ; sex pheromone ; pheromone biosynthesis ; Indian meal moth
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts of sex pheromone glands obtained from females ofPloida interpunctella contained detectable amounts of (Z,E,)-9,12-tetradecadien-1-ol acetate (Z9,E12–14:Ac) and (Z,E.)-9,12-tetradecadien-1-ol (Z9,E12–14:OH) 4 hr prior to the first scotophase after adult emergence. The amount of pheromone increased during the first 4 hr of the scotophase and then declined to low levels during the subsequent photophase. Decapitation of females immediately after emergence, prior to expansion of the wings, inhibited production of pheromone during the subsequent 48 hr. Injection of extracts of the heads of 1-day-old females ofP. interpunctella of partially purified extracts of the cephalic ganglia of females of the corn earworm moth into decapitated females stimulated production of bothZ9,E12–14:Ac andZ9,E12–14:OH as well as production of (Z,E)-9,12-tetradecadienal (Z9,E12–14:Al). This aldehyde was subsequently identified from extracts of pheromone glands obtained from naturally calling females as well as from volatiles emitted by calling females. Studies on the terminal steps in biosynthesis of the pheromone showed thatZ9,E12–14:OH was produced from the corresponding acetate and thatZ9,E12–14:Al was produced from the alcohol via the action of an oxidase(s).
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    Structure-activity relationship observations for European corn borer moth pheromone and fluoro analogs via computer molecular modeling (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1921-1930 
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    ISSN: 1573-1561
    Keywords: Molecular modeling ; SAR ; Lepidoptera ; Pyralidae ; Ostrinia nubilalis ; European corn borer moth ; sex pheromone ; attractant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Structure-activity relationship (SAR) observations were made for theZ-type European corn borer moth pheromone, (Z)-11-tetradecen-1-ol acetate, and a series of analogs with fluorination in the alcohol portion of the molecule. The attractiveness of these analogs and the pheromone was compared to the electrostatic potential map of the molecular mechanics (MM) minimized lowest energy conformation for each compound. A critical range of electrostatic potential on the protons of the double-bond appears to be essential for optimal acceptor fit and attractiveness.
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    Biological activity of chemicals identified from extracts and volatiles of maleRhagoletis cerasi (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1287-1297 
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    ISSN: 1573-1561
    Keywords: Rhagoletis cerasi ; cherry fruit fly ; Diptera ; Tephritidae ; EAG ; volatiles ; extracts ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Fractions obtained by chromatographic separation of extracts and volatiles from maleRhagoletis cerasi flies were tested for biological activity on females under laboratory conditions. During the bioassays, the number of incoming flies as well as the time spent by individual flies on the area of stimulus were taken under consideration. Two distinct types of female behavior were observed, i.e., attraction and arrestant behavior. GC-MS analysis of biologically active fractions resulted in tentative identification of 75 compounds. EAG screening for 27 of these compounds was performed, and subsequent laboratory bioassays resulted in the confirmation of arrestant activity for various mixtures of eight fatty acids (octadecanoic, nonadecanoic, eicosatetraenoic, eicosapenaenoic, eicosaenoic, heneicosanoic, docosahexenoic, and docosanoic). Following EAG tests and laboratory bioassays, a possible mode of chemical communication of this species with sex pheromones is proposed.
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    Production of pheromone by hairpencil glands of males obtained from interspecific hybridization betweenHeliothis virescens andH. subflexa (Lepidoptera: Noctuidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 59-67 
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    ISSN: 1573-1561
    Keywords: Hairpencils ; sex pheromone ; Heliothis ; autosomes ; sex chromosomes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pheromone produced by the hairpencil glands of interspecific hybrid- and backcross-generation males from crosses betweenHeliothis virescens (F.) withH. subflexa (Gn.) was studied. Males of reciprocal F1 hybrids, all of which had hairpencil glands morphologically similar to those ofH. virescens, produced neither the same pheromone blend nor amounts of pheromone that were produced by males ofH. virescens. Instead, these hybrid males produced pheromone that was quantitatively and qualitatively similar to that produced byH. subflexa. Hairpencil gland extracts from males obtained from backcrossing F1 females of either cross to males ofH. subflexa were the same as those ofH. subflexa. However, extracts from backcross males of crosses between F1 females andH. virescens were variable. Some extracts from these backcross males were like those ofH. virescens while others were either likeH. subflexa or were intermediate between those of the parent species. These results showed that the production of pheromone by the hairpencil glands of hybrid and backcross males is under the dominant regulation of autosomal genes of theH. subflexa genome.
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    Identification of an attractant for the caneborerSesamia grisescens walker (Lepidoptera: Noctuidae) (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1409-1420 
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    ISSN: 1573-1561
    Keywords: Caneborer ; sugarcane ; trapping ; electroantennogram ; sex pheromone ; attractant ; Insecta
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The composition of the sex pheromone ofSesamia grisescens was investigated using gas chromatography, electroantennograms, and field trapping. (Z)-11-Hexadecenyl acetate and (Z)-11-hexadecenol were identified in field tests as the major attractants. Trapping trials identified a 3:2 blend of these compounds as the most effective bait. Gas chromatography indicated the presence of hexadecyl acetate. (Z)-9-hexadecenyl acetate, (Z)-9-hexadecenol, and (E)-11-hexadecenyl acetate in the pheromone gland, but these compounds had no significant effect on trap catches when added to the major components. Traps baited with the major components in a 1:1 ratio caught more male moths than traps baited with virgin females.
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    URL: http://dx.doi.org/10.1007/BF02035142
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    Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 849-858 
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    ISSN: 1573-1561
    Keywords: Matsucoccus josephi ; Coccoidae ; Homoptera ; Matsucoccidae ; pine bast scales ; sex pheromone ; absolute configuration ; (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one
    Source: Springer Online Journal Archives 1860-2000
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    Notes: Abstract The absolute configuration of the sex pheromone of the Israeli pine bast scale,Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here asR-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated asS-E. The chirality of the quantitatively minorZ isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of naturalM. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemicZ andE isomers, the latter elicited the stronger antennal response by maleM. josephi. In GC-EAD of all four stereoisomers, employing the chiral column,R-E was the most active stereoisomer. In field testsR-E attracted 10 times more males ofM. josephi than didS-E. The racemicE/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many maleM. josephi as did an equivalent amount ofR-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship.
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    Codling moth,Cydia pomonella, (Lepidoptera: Tortricidae): Is its sex pheromone multicomponent? (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1065-1071 
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    ISSN: 1573-1561
    Keywords: Codling moth ; Cydia pomonella ; sex pheromone ; (E,E)-8,10-dodecadien-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract When the nine identified components in the effluvium of calling female codling moths were compared to pure synthetic (E,E)-8,10-dodecadien-1-ol in flight-tunnel tests, equal responses were obtained over a concentration range of 300-fold. When synthetic (E,E)-8,10-dodecadien-1-ol was compared to extract of female sex pheromone glands by a male wing-flutter bioassay, or in flight-tunnel tests, equal responses were obtained over a concentration range of 1000-fold. The sum total of these and previous studies indicate that the codling moth sex pheromone consists of only one component.
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    Spatial distribution of pheromone in vineyards treated for mating disruption of the grape vine mothLobesia botrana measured with electroantennograms (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 1299-1314 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Lobesia botrana ; sex pheromone ; pest control ; mating disruption ; electroantennogram ; field EAG ; vineyard
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The spatial distribution of the pheromone of the grape vine moth.Lobesia botrana (Lepidoptera: Tortricidae), was measured in vineyards treated for mating disruption by using an electroantennogram technique (EAG). Five hundred dispensers per hectare, each containing 0.1 g of the main component of the sex pheromone (E,Z)-7,9-dodecadienyl acetate (E7,Z9-12: Ac) were evenly distributed in the experimental vineyards. The EAG amplitudes measured in the experimental plots were transformed into relative pheromone concentrations by means of a calibration curve. Mean relative pheromone concentrations in the center of a treated plot reached 2.31 × 10−4 relative units. No significant differences in the mean relative pheromone concentrations were found between replicate plots (P 〉 0.01). The mean relative pheromone concentrations measured within one plot along a transect at 5-m intervals also showed no significant differences between the sites. These results indicate that inside the borders of treated areas the pheromone was evenly distributed. No sites with significantly lower pheromone concentrations, frequently assumed to be the cause for higher trap catches in some areas, were found. However, the mean relative pheromone concentration rapidly declined more than 100-fold outside the border of the treated plot. At 10 m from the treated area, the EAGs showed no significant difference compared to the EAGs recorded in an untreated area. A rapid drop in the mean relative pheromone concentration was also found on a vertical transect through the canopy of the vineyard. Measurements in an untreated control block gave a mean antennal response approximately 1000-fold lower than in a nearby pheromone treated plot. The significance of the variation in the pheromone distribution for the success of the mating-disruption method is discussed.
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    Evidence for volatile chemical attractants in the beetleMaladera matrida argaman (Coleoptera: Scarabaeidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2673-2685 
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    ISSN: 1573-1561
    Keywords: Maladera matrida ; Coleoptera ; Scarabaeidae ; collection of volatiles ; field trapping ; olfactometer ; attractants ; host plant volatiles ; synergism ; aggregation ; sex pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract TheMaladera matrida beetle (Coleoptera, Scarabaeidae, Melolonthinae), a relatively new species to science, was first identified in Israel in 1983. In the course of field observations it was found that adultM. matrida beetles emerged from the soil at sunset to feed and mate. During the first 20 min of flight, most of the beetles were males. The females emerged shortly afterwards, and aggregations numbering 20–30 individuals with equal proportions of males and females were eventually formed on peanut plants. Laboratory olfactometer bioassays showed that peanut leaves (food) attracted both males and females. Field-trapping experiments and olfactometer studies showed thatM. matrida beetles were highly attracted by live virgin females in the presence of food (cut-up peanut leaves). Another set of field trapping experiments indicated that airborne volatiles produced by live virgin females plus food had the same attracting ability as live virgin females plus food. The attraction exerted by the combination of live virgin females and peanut leave volatiles suggests a synergism effect. Accordingly, we propose a two-stage mechanism of chemical communication in theM. matrida beetles: first, the males cause mechanical damage to the host plant to attract both sexes; later, the females emit attractants (sex pheromone) while eating or shortly thereafter.
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    Pheromonal secretions from glands on the 5th abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 153-170 
    Details
    ISSN: 1573-1561
    Keywords: Trichoptera ; Rhyacophilidae ; sex pheromone ; aggregation pheromone ; Rhyacophila nubila ; Rhyacophila fasciata Hydropsyche angustipennis ; electroantennogram ; heptan-2-one ; octan-2-one ; nonan-2-one ; decan-2-one ; (Z)-6-nonen-2-one ; heptan-2-ol ; nonan-2-ol ; GC-EAD ; swarming
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts of different body parts of adult Trichoptera were tested for electrophysiological activity. Extracts of the IVth and Vth abdominal sternites of femaleHydropsyche angustipennis, Rhyacophila nubila, andR. fasciata, containing a paired exocrine gland, elicited significant electroan-tennographic responses when tested on conspecific male antennae. The paired gland occurs also in males of all the species, and inH. angustipennis, extracts from males were more active than female extracts when tested on male antennae. Female and male extracts from all species were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). EAD-active peaks in female extracts, stimulating male antennae, were identified inH. angustipennis as nonan-2-one; and inR. nubila andR. fasciata as heptan-2-one, heptan-2-ol, nonan-2-one, and nonan-2-ol. EAD-active components from maleH. angustipennis stimulating male antennae were octan-2-one, nonan-2-one (major peak), (Z)-6-nonen-2-one, decan-2-one, and a methylbranched decan-2-one. Female extracts and synthetic mixtures of compounds identified from femaleH. angustipennis andR. fasciata were tested for attractivity in the field. High catches with control traps obscured the results, but a synthetic mixture of the four identified compounds was significantly attractive and not different from female extracts for attracting maleR. fasciata. InH. angustipennis, a synthetic six-component male blend, in which nonan-2-one was the major component, attracted significant numbers of male and femaleH. angustipennis. Extracts of maleR. nubila andR. fasciata contained acetophenone and hexanoic and octanoic acids but did not have any electrophysiological or behavioral activity on either male or female antennae of conspecifics. The occurrence of a female sex pheromone inRhyacophila and an aggregation pheromone inHydropsyche corresponds to earlier described differences in mating behaviors in the Rhyacophilidae and Hydropsychidae.
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    Evolution of behavioral responses to sex pheromone in mutant laboratory colonies ofTrichoplusia ni (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 231-238 
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    ISSN: 1573-1561
    Keywords: Trichoplusia ni ; Lepidoptera ; Noctuidae ; sex pheromone ; behavior ; evolution ; sexual selection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male cabbage looper moths,Trichoplusia ni, from two colonies in which all females express an abnormal sex pheromone production phenotype were evaluated in a laboratory wind tunnel for upwind flight responses to the normal and abnormal sex pheromones. The abnormal sex pheromone blend consisted of 20 times as much (Z)-9-tetradecenyl acetate and 30-fold less (Z)-5-dodecenyl acetate compared to the normal pheromone blend. Initially, these males exhibited poor behavioral responses to the abnormal sex pheromone and maximum responses to the normal pheromone blend, indicating that there was no linkage between signal production and response. After 49 generations of laboratory rearing, males from the mutant colonies maintained good responses to the normal pheromone and increased their behavioral response to the abnormal sex pheromone to the same levels as for the normal pheromone. Over the same period, normal males maintained their preference for the normal pheromone. These results indicated that evolution had occurred in mutant colonies in favor of greater male responsiveness to the abnormal sex pheromone, resulting in the broadening of the response spectrum to pheromone blend ratios. This evolution presumably resulted from a mating advantage to those males that did not discriminate against mutant-type females in the mutant colonies.
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    Male sex pheromone of cockroachEurycotis floridana (walker) (Blattidae, Polyzosteriinae): Role and composition of tergites 2 and 8 secretions (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2291-2306 
    Details
    ISSN: 1573-1561
    Keywords: Cockroach ; Dictyoptera ; Blattidae ; Eurycotis floridana ; (2R*, 3R*)-butanediol ; dodecanol ; benzyl-2-hydroxybenzoate ; sex pheromone ; sexual behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract InEurycotis floridana, the male calling behavior is associated with the exposition of epidermal glands located under tergites 2, 7, and 8. 4-Hydroxy-5-methyl-3(2H)-furanone and 4-hydroxy-2,5-dimethyl-3(2H)-furanone were recently identified as the specific components of tergite 7 secretion. Methylene chloride extracts of tergite 7 and its major compound 4-hydroxy-5-methyl-3(2H)-furanone attract the conspecific females at a distance. Methylene chloride extracts of tergite 8 are also attractive at a distance to the females, whereas extracts of tergite 2 had no effect on males and females. Our GC investigations showed the absence of specific compounds in tergite 2 secretions. The GC-MS analyses revealed that the male secretion of the gland under tergite 8 is mainly a mixture of (2R*, 3R*)-butanediol, 1-dodecanol and benzyl 2-hydroxybenzoate. These compounds were tested at different concentrations on their own, or as a mixture. Only (2R*, 3R*)-butanediol and 1-dodecanol were attractive for the females. Their functions, as components of the male sex pheromone, in addition with the two derivatives of the furanone are discussed.
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    Identification and synthesis of female sex pheromone of Oriental beetle,Anomala orientalis (Coleoptera: Scarabaeidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2415-2427 
    Details
    ISSN: 1573-1561
    Keywords: Anomala orientalis ; Oriental beetle ; Coleoptera ; Scarabaeidae ; sex pheromone ; (Z)- and (E)-7-tetradecen-2-one ; DMDS derivatization ; flight tunnel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Females of the Oriental beetle,Anomala orientalis (Waterhouse), release a sex pheromone composed of a 9:1 blend of (Z)- and (E)-7-tetradecen-2-one. The double-bond position of the pheromone was determined by DMDS derivatization and interpretation of the fragmentation patterns produced by monounsaturated ketones. In a sustained-flight tunnel, males responded by flying toward female beetles and attempting to copulate with them. Both effluvium and whole-body extracts of OB females were analyzed, and the activity was found only in the airborne extracts. Flight-tunnel bioassays also showed that a synthetic 90:10Z/E blend on a rubber septum was attractive and that the responses of males to this blend were equivalent toZ isomer alone, but much better than to the singleE isomer.
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    (E)-11,13-tetradecadienal: Major sex pheromone component of the eastern blackheaded budworm,Acleris variana (Fern.) (Lepidoptera: Tortricidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1-8 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Acleris variana ; sex pheromone ; (E)-11,13-tetradecadienal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (E)-11,13-Tetradecadienal (E11,13–14:Ald) is the major sex pheromone component of the eastern blackheaded budworm (EBB),Acleris variana (Fern.). The compound was identified in female pheromone gland extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD), coupled GC-mass spectrometry in selected ion monitoring mode, and retention index calculations of candidate pheromone components.E11,13–14:Ald alone as trap bait was very attractive to male EBB. Addition of the corresponding diene alcohol or acetate or both did not enhance attraction. (Z)-11,13-Tetradecadienal in binary combination with (E)-11,13–14:Ald neither enhanced nor reduced trap catches. Increasing the amounts of pheromone from 0.01 to 10 µg increased trap catches, but increase of pheromone quantity above 100 µg proportionately reduced attraction. Stabilization of slowly polymerizingE11,13–14:Ald and development of a sustained, adequate release rate is required for pheromone-based monitoring of EBB populations.
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    Sex pheromone activity in a single component of tergal gland extract ofLutzomyia longipalpis (Diptera: Psychodidae) from Jacobina, Northeastern Brazil (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 141-151 
    Details
    ISSN: 1573-1561
    Keywords: sex pheromone ; tergal gland ; Lutzomyia longipalpis ; Diptera ; Psychodidae ; gas chromatography ; high-pressure liquid chromatography
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone component of maleLutzomyia longipalpis tergal gland extract was isolated and its activity confirmed by bioassay. Whole tergal gland extract was analyzed by HPLC and fractions were collected as they eluted from the detector. Each fraction was tested in an attraction bioassay with virgin unfed femaleLutzomyia longipalpis. HPLC analysis showed that whole extract contained several peaks; one large peak, one small peak and several minor peaks. Purity of the HPLC fractions was determined by GC analysis. The bioassays revealed that the large peak was responsible for most of the observed female behavior. The addition of the small peak to the large peak improved the response although by itself the small peak failed to elicit any significant behavior. Minor peaks failed to elicit any response. Chemical analysis revealed the large peak to be a relatively nonpolar hydrocarbon.
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    Codling moth (Cydia pomonella): Disruptants of sex pheromonal communication (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 171-181 
    Details
    ISSN: 1573-1561
    Keywords: Codling moth ; Cydia pomonella ; Lepidoptera ; Tortricidae ; communication disruption ; mating disruption ; sex pheromone ; (E,E)-8,10-dodecadien-1-ol ; (E,Z)-8,10-dodecadien-1-ol ; (Z,E)-8,10-dodecadien-1-ol ; dodecan-1-ol ; tetradecan-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In a small section of an apple orchard, six traps were placed each in control and test areas and baited with live virgin female codling moths. Gray elastomer septa were used to dispense communication disruptants around the traps. Dyed male codling moths were released in control and test areas, and the numbers of males captured in control and test traps were compared. In 1991, linear regression curves of percent communication disruption versus logarithm of dose were obtained for three compositions: (E,E)-8,10-dodecadien-1-ol, codlemone (1); codlemone + dodecan-1-ol + tetradecan-1-ol (2); and an equilibrium mixture of the four isomers of 8,10-dodecadien-1-ol (30, (61%EE, 14%ZE, 20%EZ, and 5%ZZ). All three regressions gaver 2 values greater than 0.90. At the 95% confidence limits, slopes and intercepts of compositions 1 and 2 were equivalent, and different from that of composition 3, which produced the greatest percentages of disruption at all doses. In 1992, five treatments were compared at a single dose: 1, 3, none (4), (Z,E)-8,10-dodecadien-1-ol (5), (E,Z)-8,10-dodecadien-1-ol (6). Compositions 5 and 6 gave the greatest and similar percentages of disruption and were different from codlemone (1) and 4 (95% confidence), but not from composition 3. Communication disruption produced by composition 3 was greater than (codlemone), which was greater than 4.
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    Electrophysiological and field activity of halogenated analogs of (E,E)-8,10-dodecadien-1-ol, the main pheromone component, in codling moth (Cydia pomonella L.) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 489-503 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Cydia pomonella ; codling moth ; sex pheromone ; halogenated analogs ; isosteric replacements ; EAG ; single sensillum recording ; field trapping ; structure-activity relationship ; codlemone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pest monitoring and control of the codling moth,Cydia pomonella L., have been developed using the main pheromone component of this species, (E,E)-8,10-dodecadienol (codlemone). However, the activity of codlemone is not satisfactory for pest control by mating disruption. Thus, we have synthesized halogenated analogs of codlemone to see if they could be used as new agents for pest control of the codling moth. Their biological activity was measured by electrophysiological techniques. In EAG screening, codlemone was the most active compound. F(10,11)-codlemone [(E,E)-10,11-difluoro-8,10-dodecadienol] and Cl-codlemone [(E,E)-11-chloro-8,10-undecadienol] elicited significant EAG responses, F(10,11)-codlemone triggering responses not significantly different from responses to codlemone. EAG cross-adaptation experiments and single sensillum recordings revealed that these compounds were detected by the same receptor neuron type as codlemone. No competitive inhibition with codlemone was observed from nonactive compounds. In field trapping, F(10,11)-codlemone and Cl-codlemone were more attractive to male codling moths than codlemone itself. Possible explanations of this activity are discussed.
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    Response of male eye-spotted bud moth,Spilonota ocellana (Lepidoptera: Tortricidae), to different pheromone blends in north America and The Netherlands (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 625-630 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Spilonota ocellana ; eye-spotted bud moth ; sex pheromone ; (Z)-8-tetradecenyl acetate and (Z)-8-tetradecenyl alcohol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Response of male eye-spotted bud moth,Spilonota ocellana (Denis and Schiffermüller), to different ratios of synthetic sex pheromone components, (Z)-8-tetradecenyl acetate (Z8-14:OAc) and (Z)-8-tetradecenyl alcohol (Z8-14:OH), were compared in four North American locations and in one location in The Netherlands. In British Columbia, Nova Scotia, Michigan, and The Netherlands, a 99:1 blend ofZ8-14:OAc andZ8-14:OH captured significantly more maleS. ocellana thanZ8-14:OAc alone or binary blends containing 10–50%Z8-14:OH. In Ontario, where population sizes were low compared to the other four locations, trends in trap catches were similar, and there was no indication that maleS. ocellana responded differently to the tested pheromone blends. A 99:1 blend ofZ8-14:OAc andZ8-14:OH should be most effective in pheromone-based control programs ofS. ocellana in North America and in The Netherlands. Our results confirm earlier studies that a 99:1 blend ofZ8-14:OAc andZ8-14:OH captures significantly more maleS. ocellana thanZ8-14:OAc alone. However, our finding that a 99:1 blend ofZ8-14:OAc andZ8-14:OH is significantly more attractive than binary blends containing 10–50%Z8-14:OH differs from previous findings in Germany and Switzerland.
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    Field response of maritime pine scale,Matsucoccus feytaudi duc. (Homoptera: Margarodidae), to synthetic sex pheromone stereoisomers (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2159-2170 
    Details
    ISSN: 1573-1561
    Keywords: Maritime pine scale ; Matsucoccus feytaudi ; Homoptera ; Margarodidae ; sex pheromone ; field trapping ; (8E,10E)-3,7,9-trimethyl-8,10-dodecadien-6-one ; absolute configuration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The absolute configuration of the primary component of the maritime pine scale (Matsucoccus feytaudi) pheromone (i.e., (8E, 10E)-3,7,9-trimethyl-8,10-dodecadien-6-one) was determined as 3S,7R by field-trapping experiments using synthetic stereoisomers and according to previous NMR considerations. The 3R,7R isomer showed similar activity to 3S,7R, whereasM. feytaudi males responded very weakly to the two other candidates (3R,7S and 3S,7S). Further studies were conducted to optimize scale trapping for monitoring scale populations. Results of these studies showed that the trapping efficiency was related to pheromone dose, trap area, and wind speed but not to trap height.
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    URL: http://dx.doi.org/10.1007/BF02033194
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    Response ofMatsucoccus thunbergianae males to synthetic sex pheromone and its utilization for monitoring the spread of infestation (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2185-2196 
    Details
    ISSN: 1573-1561
    Keywords: Matsucoccus thunbergianae ; Homoptera ; Coccoidea ; Margarodidae ; black pine bast scale ; sex pheromone ; attractant ; (2E,4E6R,10R)-4 ; 6,10,12-tetramethyl-2,4-tridecadien-7-one ; matsuone ; monitoring ; detection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Attraction of (2E,4E,6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one [1; (6R,10R)-matsuone] and its antipode [2; (6S,10S)-matsuone] toMatsucoccus thunbergianae males was studied in the laboratory and in the field. They showed stronger response to1. In laboratory bioassays, the threshold concentrations for male attraction with1 and2 were 16 fg and 150 pg, respectively. In the field, during the first two days after traps were set, traps baited with 50 µg of1 on rubber septa or filter paper rolls caught more males than control traps. Between the sixth day and the tenth day after traps were set, in a daily trap catch experiment, the traps with 50 µg of1 on filter paper rolls caught more males than control traps on one day only, whereas those on rubber septa were always effective. The shape of the traps did not affect male catches. Males were caught on pheromone traps in locations where no scales were found by the customary detecting procedures.
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    Sex pheromone components of the spring hemlock looper,Lambdina athasaria (Walker) (Lepidoptera: Geometridae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2501-2511 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Lambdina athasaria ; Lambdina fiscellaria fiscellaria ; Lambdina fiscellaria lugubrosa ; sex pheromone ; synergism ; 7,11-dimethylheptadecane ; 7-methylheptadecane ; 5,11-dimethylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two methylated hydrocarbons, 7-methylheptadecane (7) and 7,11-dimethylheptadecane (7,11), are female sex pheromone components of the spring hemlock looper (SHL),Lambdina athasaria (Walker). Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometry (GC-MS) in selected ion monitoring mode. In field trapping experiments, (7) and (7,11) by themselves were behaviorally inactive, but in combination attracted numerous male moths. (5,11)-Dimethylheptadecane (5,11) was detected in female SHL pheromone gland extracts, but did not enhance attraction to the binary blend of (7) and (7,11). The sex pheromone of SHL is related to that of congeneric eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria (Guen.) [(5,11) and 2,5-dimethylheptadecane (2,5)] and western hemlock looper (WHL),L.f. lugubrosa (Hulst) [(5,11), (2,5) and (7)]. Specificity of the pheromonal blend, spatial separation of coseasonal EHL and WHL, and temporal separation of sympatric EHL and SHL contribute to reproductive isolation.
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    (Z,Z)-5,27-Tritriacontadiene: Major sex pheromone ofDrosophila pallidosa (Diptera; Drosophilidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3029-3037 
    Details
    ISSN: 1573-1561
    Keywords: Drosophila pallidosa ; Diptera ; Drosophilidae ; sex pheromone ; cuticular hydrocarbon ; (Z,Z)-5,27-tritriacontadiene ; courtship behavior ; fruit fly
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A crude cuticular extract from both sexes of 3660 fruit flies (Drosophila pallidosa) was subjected to SiO2 and AgNO3/SiO2 column chromatography, accompanied by bioassay for the sex pheromone activity. After three chromatographic steps, the active fraction was obtained. The main component of the active fraction was determined to be (Z,Z)-5,27-tritriacontadiene [(Z,Z)-5,27-C33:2, on the basis of gas-liquid chromatographic analysis, chemical derivatization and gas chromatography-mass spectrometry. Synthetic (Z,Z)-5,27-C33:2 at 5 female equivalents (FE) elicited a clear courtship response with a high courtship index amongD. pallidosa males. Therefore it was concluded that (Z,Z)-5,27-C33:2 was a major sex pheromone component in this species.
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    Bisabolene epoxides in sex pheromone innezara viridula (L.) (Heteroptera: Pentatomidae): Role ofcis isomer and relation to specificity of pheromone (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3133-3147 
    Details
    ISSN: 1573-1561
    Keywords: Nezara viridula ; Heteroptera ; Pentatomidae ; sex pheromone ; trans- andcis-(Z)-α-bisabolene epoxides ; interindividual variation ; bioassay ; pheromonal specificity ; isomer ; enantiomer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Thetrans- andcis-(Z)-α-bisabolene epoxides (trans- andcis-(Z)-αBE) are the main components of the male sex pheromone inNezara viridula. The role of thecis isomer and the importance of thecis/trans proportion for the activity and the specificity of the pheromone are not clearly elucidated and were studied here. Interindividual variation of thecis/trans proportion produced by males was studied by individual hexanic extracts in two strains originating from the south of France (SF) and French West Indies (FWI). Thetrans isomer composed 42–82% of bisabolene epoxides in SF males and 74–94% of bisabolene epoxides in FWI males. Means (± SD) significantly differ between SF (62.8%±8.4) and FWI (82.4%±5.9) males in spite of this interindividual variation. Different isomers of bisabolene epoxide were synthesized and their EAG activity on female antennae was compared. Racemictrans- andcis-(Z)-αBE elicited low EAGs, not different from the nonnaturaltrans andcis (E)-αBE that were inactive on behavior. Behavioral tests revealed that racemictrans- andcis-(Z)-αBE attracted 45% (P〈0.05) and 25% (P〈0.05) of females, respectively. The same levels of attraction were obtained with (−) enantiomers oftrans- andcis-(Z)-αBE, which attracted 40% (P〈0.05) and 20% (P〉0.05) of the females, respectively. Binary blends containing 75/25, 50/50, and 25/75 proportions ofcis/trans isomers were more attractive thantrans-(Z)-αBE alone and response of females to the 25%cis/75%trans blend was significantly more important than the response totrans-isomer alone (P〈0.05). The importance of thecis/trans proportion in relation with the specificity of the male pheromone is discussed.
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    Sex pheromone of cranberry fruitworm,Acrobasis vaccinii riley (Lepidoptera: Pyralidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3269-3279 
    Details
    ISSN: 1573-1561
    Keywords: Cranberry fruitworm ; Lepidoptera ; Pyralidae ; Acrobasis vaccinii ; sex pheromone ; (E,Z)-8,10-pentadecadien-l-ol acetate ; (E)-9-pentadecen-l-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The following compounds and (approximate ratios) were identified in sex pheromone gland extracts of femaleAcrobasis vaccinii Riley by comparison of gas chromatography-mass spectrometric traces with those of synthetic standards: (E,Z)-, (Z,E)-, (Z,Z), and (E,E)-8, 10-pentadecadien-l-ol acetates (100:1:2:12), a dodecen-l-ol acetate (8), (Z)-8-, (Z)-9-, and (E)-9-pentadecen-l-ol acetates (3:23:4), two heptadecen-l-ol acetates (4:4), tetradecyl, pentadecyl, hexadecyl, and heptadecyl acetates (3:15:10:8), dodecan-l-ol (6), tetradecan-l-ol (5), and hexadecan-l-ol (23). The amount of (E,Z)-8, 10-pentadecadien-l-ol acetate (E8,Z10–15:Ac) in the extract was about 0.5 ng/female. Electroantennographic analysis of gas chromatographic fractions of female sex pheromone gland extract showed that the fraction containingE8,Z10–15:Ac elicited the greatest response. Alone,E8,Z10–15:Ac failed to elicit upwind flight of males in flight-tunnel tests, and traps baited with it did not catch males in field experiments. WhenE8,Z10–15:Ac was combined with (E)-9-pentadecen-l-ol acetate (100:4), male upwind flight response in flight-tunnel tests was equivalent to those obtained with extract of female sex pheromone glands (synthetic, 62%; natural, 51%), but the percent of males flying upwind that contacted the source was lower (synthetic, 47%; natural, 88%). The lower percent of source contact elicited by the synthetic pheromone could be a result of the difference in isomer ratios of 8,10–15:Ac in the natural and synthetic pheromone or could indicate that the synthetic pheromone is incomplete. Traps baited with the 100:4 combination caught large numbers of males in field experiments.
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    Behavioral and electrophysiological response of cabbage seed weevils (Ceutorhynchus assimilis) to conspecific odor (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 979-989 
    Details
    ISSN: 1573-1561
    Keywords: Ceutorhynchus assimilis ; Coleoptera ; Curculionidae ; olfactometer ; sex pheromone ; aggregation pheromone ; electroantennogram
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The responses ofCeutorhynchus assimilis Payk. (Coleoptera, Curculionidae) to the odor of overwintered and new generation weevils were studied using an olfactometer, choice tests in a laboratory cage, field tests using sticky traps baited with live weevils, and by electroantennograms (EAG's). Unmated male weevils and, to a lesser extent, female weevils of the overwintered generation were attracted to the odor of live unmated over-wintered female weevils. New generation weevils exhibited no behavioral response to conspecific odor. Male and female weevils of the overwintered generation exhibited positive EAGs to hexane extracts of overwintered female weevils, whereas EAGs of new-generation weevils of either sex were unresponsive to these extracts. This suggests that the unmated female weevils from the overwintered generation produce a volatile chemical or chemicals that attracts unmated male and female weevils. The new generation of female weevils does not produce this attractive chemical before overwintering, and male and female weevils of this generation can not detect the chemical(s) via their antennal chemoreceptors until they have undergone their overwintering period.
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    Kairomone from dandelion,Taraxacum officinale, attractant for scarab beetleAnomala octiescostata (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1697-1704 
    Details
    ISSN: 1573-1561
    Keywords: cis-3-Hexenyl acetate ; benzaldehyde ; phenylacetaldehyde ; benzyl alcohol ; phenethyl alcohol ; phenylacetonitrile ; benzyl benzoate ; anethol ; geraniol ; phenethyl propionate ; kairomone ; sex pheromone ; dandelion ; Taraxacum officionale ; Coleoptera ; Scarabidae ; Anomala oritescostata ; scarab beetle
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The attraction of the scarab beetleAnomala octiescostata to dandelion,Taraxacum officinale, was demonstrated to be chemically mediated by a mixture ofcis-3-hexenyl acetate, benzaldehyde, phenylacetaldehyde, benzyl alcohol, phenethyl alcohol, phenylacetonitrile, and benzyl benzoate, in the ratio 4:8:14:3:5:19:11. Combination of the synthetic kairomone and sex pheromone (buibuilactone + japonilure, 8:2), significantly increased the total catches ofA. octiescostata. Catches of male (but not female) beetles were significantly higher with the kairomone-pheromone blend than with kairomone alone. The synergistic effect of the kairomone from dandelion on the attractiveness did not significantly differ from that of a food-type lure, anethol, geraniol, and phenethyl propionate (9:0.5:0.5). The latter combined with the synthetic sex pheromone resulted in better attraction of female (but not male)A. octiescostata than the sex pheromone alone.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059891
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    Chiral esters: Sex pheromone of the bagworm,Oiketicus kirbyi (Lepidoptera: Psychidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3083-3096 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Psychidae ; Oiketicus kirbyi ; bagworm ; sex pheromone ; pheromone chirality ; 1-methylbutyl octanoate ; 1-methylbutyl non-anoate ; 1-methylbutyl decanoate ; 1-methylbutyl dodecanoate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract of female bagworms,Oiketicus kirbyi (Guilding), revealed five EAD-active compounds. Retention index calculations, GC-mass spectrometry in both full-scan and selected-ion monitoring modes and GC-EAD analyses of authentic standards identified the compounds as 1-methylbutyl octanoate (MBO), 1-methylbutyl nonanoate (MBN), 1-methylbutyl decanoate (MBD), 1-methylpentyl decanoate (MPD), and 1-methylbutyl dodecanoate (MBDD). Of these five chiral esters, MBD was most abundant in extracts and elicited the strongest antennal response. In field experiments in Costa Rica, (R)-MBD attractedO. kirbyi males, whereas (S)-MBD in combination with (R)-MBD inhibited response.R but notS enantiomers of MBO, MBN, and MBDD strongly synergized attraction to (R)-MBD. (S)-MBO and (S)-MBDD were inactive, whereas (S)-MBN was inhibitory. (R)-, (S)- and racemic MPD were inactive. Blends of (R)-MBD in ternary combination with either (R)-MBO and (R)-MBN or (R)-MBN and (R)-MBDD were as attractive as the five-ester blend. Five- and four-ester blends were equally attractive, suggesting redundancy of pheromone components for attraction of males. The multiple sex pheromone component blend of chiral esters inO. kirbyi may have evolved to maintain species-specific communication in bagworm communities of tropical Americas.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033712
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  • 92
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    Unusual periodicity of sex pheromone production in the large black chaferHolotrichia parallela (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1381-1391 
    Details
    ISSN: 1573-1561
    Keywords: Holotrichia parallela ; large black chafer ; scarab beetle ; Coleoptera ; Scarabaeidae ; isoleucine methyl ester ; linalool ; sex pheromone ; circabidian periodicity ; pheromone titer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (R)-(−)-Linalool was identified as a minor component sex pheromone of the scarab beetleHolotrichia parallela (Coleoptera: Scarabaeidae). Field evaluations revealed that, although not attractive per se, (R)-(−)-linalool enhances the attractiveness of the major sex pheromone,L-isoleucine methyl ester (LIME). Analyses of the pheromone titers in the glands of field-collected females demonstrated the occurrence of peak levels of 48-hr (“circabidian”) periodicity. The levels of LIME in the glands of 45-day-old virgin females increased over three times from the scototo the photophase of a calling day, but the amounts of (R)-(−)-linalool did not significantly change. Virgin females had in average two times more LIME and 3.6 times more (R)-(−)-linalool than the average amount found in the field-captured beetles throughout the season.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984883
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  • 93
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    Field evaluation ofAnomala schonfeldti ohaus (Coleoptera: Scarabaeidae) synthetic sex pheromone (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1453-1459 
    Details
    ISSN: 1573-1561
    Keywords: Anomala schonfeldti ; Popillia japonica ; scarab beetle ; Coleoptera ; Scarabaeidae ; 2-(E)-nonenol ; sex pheromone ; mark-and-recapture ; field test ; mass trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Synthetic 2-(E)-nonenol, previously identified as the sex pheromone ofAnomala schonfeldti (Coleoptera: Scarabaeidae), is demonstrated to be very attractive to males in the field. Nevertheless, no significant differences were found between treatments with 1, 5, 10, and 20 mg dosages. Males ofA. schonfeldti were more significantly attracted to traps at 30 cm high than at 90 cm. Although the observed behavior seemed to indicate a trend of more attraction to buried traps than those placed at 30 cm, there was no statistical difference between the two treatments. Pheromone-baited traps caught significantly more beetles than traps containing three virgin females. Over 70% of released beetles were recaptured in six traps surrounding the point of release and separated from each other by 50 m, suggesting a possible use of the pheromone (in combination with floral compounds) in mass trapping.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984889
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  • 94
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    Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer,Eldana saccharina walker (Lepidoptera: Pyralidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2255-2277 
    Details
    ISSN: 1573-1561
    Keywords: Eldana saccharina ; Lepidoptera ; Pyralidae ; exocrine secretions ; sex pheromone ; aggregation pheromone ; electroantennograms ; electroantennographic detection ; NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In addition totrans-3,7-dimethyl-6-octen-4-olide (eldanolide), vanillin, and 4-hydroxybenzaldehyde, identified by French workers in the wing gland and abdominal hair pencil secretions of the male African sugarcane borer,Eldana saccharina, we have, in an earlier note, reported the presence of several other terpenoid, aromatic, and unbranched-chain compounds such as, (Z)-3,7-dimethylocta-2,6-dienoic acid, 6,10,14-trimethyl-2-pentadecanol, 4-hydroxy-3-methoxybenzyl alcohol, 1-octadecane thiol, 16-hexadecanolide, and 18-octadecanolide in these secretions. In the present paper experimental details and spectral evidence supporting the identification of these compounds, as well as the identification of (Z)-9-hexadecenal and cw-3,7-di-methyl-6-octen-4-olide (cis-eldanolide), are reported. Using electroantennography it was found that male and female antennae reacted approximately equally strongly to both secretions. This result was confirmed in analyses of the secretions using coupled gas chromatography-electroantennography and it was found that male as well as female antennae responded to eldanolide. Vanillin, substituted phenols related to vanillin, and some oxygenated monoterpenes elicited weak responses in male and female antennae. In some analyses 6,10,14-trimethyl-2-pentadecanol, present in the secretions of the insect, gave a strong antennal response. The results obtained in dynamic and static headspace determinations showed that several of the organic compounds present in the glandular secretions are released in detectable quantities and are present in widely varying quantitative ratios in the effluvia of individual calling male moths.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00979662
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  • 95
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    Diel rhythms of calling behavior and pheromone production of oriental tobacco budworm moth,Helicoverpa assulta (Lepidoptera: Noctuidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2953-2963 
    Details
    ISSN: 1573-1561
    Keywords: Helicoverpa assulta ; sex pheromone ; calling ; diel periodicity ; Lepidoptera ; Noctuidae ; (Z)-9-hexadecenal ; hexadecanal ; (Z)-11-hexadecenal ; (Z)-9-hexadecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Both calling behavior and titer of (Z)-9-hexadecenal (Z9-16: Al), the major sex pheromone component ofHelicoverpa assulta, in pheromone glands showed distinct diel periodicity, and these two were synchronous. Calling was most actively performed and the pheromone titer reached a maximum from 2 to 6 h after lights-off. During photophase, no calling was shown and only a relatively small amount of Z9-16:A1 was detected. However, there was a time lag of a few days between peak calling activity and maximum pheromone titer. The pheromone titer was maximal from age 1 day to age 5 days and thereafter decreased while calling was most actively performed after age 3 days. Titers of three minor components, hexadecenal, (Z)-11-hexadecenal, and (Z)-9-hexadecenyl acetate, showed similar daily fluctuation patterns to that of Z9-16:Al, but relative to the titer of Z9-16:Al, the titer of the two aldehyde components remained relatively constant whereas that ofZ9-16:Ac increased in the late scotophase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00980595
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    (6Z,9Z-3R,4S)-Epoxy-heptadecadiene: major sex pheromone component of the larch looper,Semiothisa sexmaculata (Packard) (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 843-850 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Semiothisa ; S. sexmaculata ; S. marmorata ; S. neptaria ; sex pheromone ; sex attractant ; enantiomer ; (3Z,6Z,9Z)-heptadecatriene ; (6Z,9Z-3R,4S)-epoxy-heptadecadiene ; (6Z,9Z-3S,4R)-epoxy-heptadecadiene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic-electroantennographic analysis (GC-EAD) of female larch looper,Semiothisa sexmaculata (Packard), gland extracts revealed two EAD-active compounds. Retention index calculations, GC-mass spectroscopy in selected ion monitoring mode, and GC-EAD analysis of authentic standards identified the compounds as (3Z,6Z,9Z)-heptadecatriene (3Z,6Z,9Z-17∶H) and (6Z,9Z)-cis-3,4-epoxy-heptadecadiene (6Z,9Z-cis-3,4-epoxy-17∶H). Chirality determination of the monoepoxydiene in gland extracts was impeded by small quantities, but field experiments indicated that maleS. sexmaculata were most strongly attracted to enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17∶H (69% ee), while maleS. neptaria (Guenée) responded well to various blends of theR,S- and S,R-epoxide enantiomers. Binary combinations of theR,S-epoxide enantiomer with 3Z,6Z,9Z-17∶H significantly inhibited response by maleS. sexmaculata, but strongly enhanced attraction of sympatric maleS. marmorata Ferguson. Enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17∶H can be used as a trap bait to monitor populations of the larch-defoliatingS. sexmaculata. Whether 6Z,9Z-3R,4S-epoxy-17∶H serves as single component sex pheromone inS. sexmaculata or small amounts of 6Z,9Z-3S,4R-epoxy-17∶H synergize or suppress optimal attraction, will be tested as chirally pure monoepoxydienes become available.
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    URL: http://dx.doi.org/10.1007/BF00985014
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    Male response to natural sex pheromone ofMigdolus fryanus westwood (Coleoptera: Cerambycidae) females as affected by daily climatic factors (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2347-2351 
    Details
    ISSN: 1573-1561
    Keywords: Migdolus fryanus ; Coleoptera ; Cerambycidae ; mating behavior ; sex pheromone ; climatic factors
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Males of the sugarcane borer,Migdolus fryanus (Coleoptera: Cerambycidae), are attracted to females by means of a sex pheromone. Mating usually occurs during a few days from October to March under field conditions in São Paulo State, Brazil. This work reports on mating of this species as affected by daily climatic factors, during a single nuptial flight. Maximum male capture by the natural sex pheromone occurred from 10∶00 to 11∶00 AM at air and soil temperatures of 30.0°C and relative humidity of 57.0%. As these temperatures increased, females burrowed into the soil, as they are more sensitive to heat than males. Thus, it was concluded that sex pheromone-mediated mating in this cerambycid is directly affected by temperatures of air and soil.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00979669
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    Chirality of 5,11-dimethylheptadecane, the major sex pheromone component of the hemlock looper,Lambdina fiscellaria (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1057-1062 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; eastern hemlock looper ; western hemlock looper ; sex pheromone ; pheromone chirality ; dimethylated hydrocarbons ; field trapping ; electrophysiological recordings ; (5R, 11S)-5 ; 11-di-methylheptadecane ; (55,11R-5 ; 11-dimethylheptadecane ; (5R, 11R-5 ; 11-di-methylheptadecane ; (5S,11S)-5 ; 11-dimethyIheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Of the four possible stereoisomers of 5,11-dimethylheptadecane, the major sex pheromone component of the eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria Guen., and the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa Hulst, (5R,11S)-5,11-dimethylheptadecane was the only stereoisomer eliciting electrophysiological responses by male EHL and WHL antennae. In field bioassays with EHL and WHL populations, traps baited with (5R,11S)-5, 11-dimethylheptadecane caught as many males as did traps baited with all four stereoisomers combined or a synthetic mixture of 5,11-dimethylheptadecanes. Catches in traps baited with the other three stereoisomers did not significantly differ from those in the unbaited control traps. We conclude that male antennae lack chemoreceptors for the other three stereoisomers of 5,11-dimethylheptadecane and hypothesize that only (5R,115)-5,11-dimethylheptadecane is produced by female EHLs and WHLs.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987368
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  • 99
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    The scarab beetleAnomala cuprea utilizes the sex pheromone ofPopillia japonica as a minor component (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1303-1313 
    Details
    ISSN: 1573-1561
    Keywords: Japanese beetle ; cupreous chafer ; GC-EAD ; (R,Z)-5-(−)-(oct-1-enyl)oxacyclopentan-2-one ; (R,Z)-5-(−)-(dec-1-enyl)oxacyclopentan-2-one ; sex pheromone ; Anomala cuprea ; Popillia japonica ; Coleoptera ; Scarabaeidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract GC-EAD analyses revealed that the scarab beetleAnomala cuprea, the cupreous chafer, utilizes, in addition to the previously identified major sex pheromone (R,Z)-5-(−)-(oct-1-enyl)oxacyclopentan-2-one, a minor component, (R,Z)-5-(−)-(dec-1-enyl)oxacyclopentan-2-one, which has been previously identified as the sex pheromone of the Japanese beetle. Release of the sex pheromone blend did not significantly differ when collected from feeding or starving female beetles, nor did it differ from volatiles collected in the scoto- and photophase. However, after mating, the amount and the ratio of the two components changed. Field tests revealed that traps baited with the synthetic sex pheromone captured more beetles than traps containing only virgin females. Based on field experiments, 10 mg of a 90∶10 blend of the pheromone was suggested as appropriate for monitoring of the cupreous chafer, although the optimal ratio for attractiveness is yet to be established. The occurrence of minor components in the pheromone system of other scarab beetles is also discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984877
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    3,13-Dimethylheptadecane: Major sex pheromone component of the western false hemlock looper,Nepytia freemani Munroe (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1501-1510 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; sex pheromone ; 3,13-dimethylheptadecane ; 3,13-dimethylhexadecane ; 3, 13-dimethyloctadecane ; 5,13-dimethylheptadecane ; 3,11 -dimethylhexadecane ; 3, 11-dimethylpentadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 3,13-Dimethylheptadecane (3,13-dime-17Hy) is the major sex pheromone component of the western false hemlock looper (WFHL),Nepytia freemani Munroe. It was identified in extracts of female pheromone glands by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectroscopy (GC-MS). Traps baited with 100μg of 3,13-dime-17Hy attracted large numbers of male WFHL. Of five additional candidate pheromone dimethylated hydrocarbons, only 3,13-dimethylhexadecane attracted male WFHL. However, neither 3,13-dime-16Hy nor the other four compounds enhanced attraction to 3,13-dime-17Hy when tested in binary or ternary combination at respective ratios of 100∶10, 100∶1, or 100∶1∶1. Identification of the complete WFHL sex pheromone requires structural elucidation of all 12 EAD-active components in gland extracts, determination of their chirality, and field testing of antennally active isomers in appropriate combinations and ratios. Stereoisomeric 3,13-dime-17Hy as trap bait may already be used to monitor WFHL populations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984893
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