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  • 1
    ISSN: 1573-1561
    Keywords: Pine sawflies ; Neodiprion spp. ; Hymenoptera ; Diprionidae ; electroantennogram ; sex pheromone ; isomers ; jack pine ; Pinus banksiana ; diprionol ; 3,7-dimethylpentadecan-2-ol ; acetate ; propionate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Several species of monophagous jack pine sawflies (Hymenoptera: Diprionidae) were tested in the field and by electroantennograms (EAG) for activity toward the optical isomers of a pine sawfly sex pheromone, the acetate and propionate esters of 3,7-dimethylpentadecan-2-ol.Neodiprion rugifrons andNeodiprion dubiosus were attracted to a mixture of the propionate esters of the 2S,3R,7R and 2S,3R,7S isomers, whereasNeodiprion swainei was attracted to the 2S,3S,7S propionate isomer. Samples containing the 2S,3R,7S propionate isomer elicited the strongest EAG responses in these three species andNeodiprion nigroscutum. The 2S,3S,7S propionate isomer was equally active (EAG) in the case ofN. swainei.
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  • 2
    ISSN: 1573-1561
    Keywords: Sawflies ; Neodiprion nanulus ; Neodiprion sertifier ; Hymenoptera ; Diprionidae ; pheromones ; chiral ; chirality ; 3,7-dimethylpentadecan-2-yl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The male red pine sawflyNeodiprion nanulus nanulus Schedl responds mainly to the (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2S,3S,7S-A) in the field. No other isomer is as effective by itself or syner-gizes 2S,3S, 7S-A in this species. ForNeodiprion sertifer (Geoffroy), however, we confirmed our earlier report that males responded significantly to a 5∶0.003 mixture of 2S,3S,7S-A and either 2S,3R,7R-A or 2S,3R,7R/S-A. The 2S,3S,7S-A isomer was separated from 2S,3R,7R-A by capillary gas-liquid chromatographic (GLC) analysis using Carbowax 20 M and DB-5 columns. The latter column also separated 2S,3S,7S-A from 2S,3R,7S-A. Only 2S,3S,7S-A was found in the natural pheromones ofN. n. nanulus andN. sertifer by GLC analysis.
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  • 3
    ISSN: 1573-1561
    Keywords: Aggregation ; Brachymeria ; Hymenoptera ; Chalcididae ; 3-hexanone ; parasitoid ; pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The parasitoidsB. intermedia andB. lasus aggregate at sites previously frequented. Extracts from filter paper conditioned by aggregated parasitoids were chromatographed (adsorption column and gas-liquid chromatography) and bioassayed. An active component that elicited aggregation response forB. intermedia was isolated and identified as 3-hexanone. This molecule was found in trace quantities (5–10 ng/female or male) on filter paper conditioned by either male, female or a combination of the sexes.
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  • 4
    ISSN: 1573-1561
    Keywords: Social wasp ; Polistes fuscatus ; Hymenoptera ; Vespidae ; Formicidae ; ant repellent ; defensive allomone ; fatty acid esters ; methyl myristate ; methyl palmitate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two active components were isolated from the ant repellent secretion produced by glandular cells on the sixth (terminal) gastral sternite ofPolistes fuscatus (F.) females. One of the components was identified as methyl palmitate. Field bioassays with synthetic methyl palmitate showed it had repellent activity againstSolenopsis geminata (F.)Forelius pruinosus (Roger), andPheidole sp. The effectiveness of the repellent was greater againstF. pruinosus andPheidole sp. than againstS. geminata. Four methyl ester homologs of methyl palmitate also were field tested for repellent activity: methyl myristate had repellent activity against all three ant species, whereas methyl stearate, methyl linoleate, and methyl linolenate exhibited no repellency.
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  • 5
    ISSN: 1573-1561
    Keywords: Brachymeria intermedia ; Brachymeria lasus ; courtship behavior ; chromatography ; sex pheromone ; Chalcididae ; Hymenoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The pheromonal basis of the courtship behavior of two gypsy moth parasitoids,Brachymeria intermedia andBrachymeria lasus, was traced to a single component in each case. This component was isolated by a combination of absorption and gas-liquid chromatography and shown to elicit some of the courtship behavior typical of these species. Bioassays of extracts from several independent techniques for sequestering pheromones, as well as interspecific assays, support this conclusion. Comparative analyses of both male and female extracts by capillary chromatography show the uniqueness of the pheromonal peak to the female volatile profile.
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  • 6
    ISSN: 1573-1561
    Keywords: Synthetic attractant ; introduced pine sawfly ; chiral specificity ; Diprion similis ; Gilpinia frutetorum ; esters ; 2S,3S,7S-3,7-dimethylpenta-decan-2-ol acetate and propionate ; Hymenoptera ; Diprionidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field attractiveness of synthetic attractants toward males of two introduced species of sawflies was examined. It was first established that the esters of 2S,3S,7S-3, 7-dimethylpentadecan-2-ol (diprionol), which have been active toward males of manyNeodiprion species, were inactive toward males ofDiprion similis andGilpinia frutetorum, To determine the chiral combination of the alcohol moiety, four different isomers, each containing specific chirally defined carbons, were synthesized. As a result it was concluded that the most active chiral arrangement of diprionol for these species is 2S, 3R, 7R.
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  • 7
    ISSN: 1573-1561
    Keywords: Red-headed pine sawfly ; Neodiprion lecontei ; Hymenoptera ; Tenthredinidae ; electroantennogram ; field tests ; sex pheromone ; 3,7-dimethylpentadecan-2-yl acetate ; 3,7-dimethylpentadecan-2-yl propionate ; optical isomers ; enantiomers ; esters
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sawfly sex pheromones, the acetate and propionate esters of 3,7-dimethylpentadecan-2-ol, were field tested for activity towardNeodiprion lecontei (Fitch). Only the acetate form of the 2S,3S,7S isomer was active. Field catch decreased with the addition of the 2S,3R,7(R/S) acetate isomer sample. Electroantennogram recordings showed a positive correlation between response and degree to which the chirality of each isomer resembled the attractive isomer.
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  • 8
    ISSN: 1573-1561
    Keywords: Neodiprion lecontei ; Hymenoptera ; Diprionidae ; 3,7-di-methylpentadecan-2-ol acetate ; trapping ; pheromone ; time of year ; time of day
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Field tests using the sawfly pheromone [3,7-dimethylpentadecan-2-ol acetate with (−)-erythro configuration (2S,3S)] were conducted near Gainesville, Florida, during 1978–1981 to determine the attraction ofNeodiprion lecontei males to baited traps with respect to time of year and time of day. Greatest numbers of males were caught during May, July, and September in traps placed within a pine stand from July 1978 to July 1979. Males were only caught between 1400 and 2000 hr on 10 dates in June and 10 dates in September–October 1980, and 10 dates in June 1981, with greatest catches from 1600–1800 hr. Catches in a synthetic-baited trap and in virgin female-baited traps were similar with respect to time of day.
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  • 9
    ISSN: 1573-1561
    Keywords: Neodiprion sertifer ; European pine sawfly ; Hymenoptera ; Tenthredinidae ; 3,7-dimethylpentadecan-2-yl acetate and propionate ; optical isomers ; enantiomers ; esters
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Among optical isomers of 3,7-dimethylpentadecan-2-ol (diprionol) acetate or propionate tested as synthetic attractants, the 2S, 3S, and 7S isomers were most effective in attracting the males ofNeodiprion sertifer in the field. The 2S, 3S, and 7R isomers showed weak activity, but the other optical isomers were not attractive. Capillary GC analysis showed that the natural pheromone from body extracts of females was identical with the synthetic acetate of diprionol in its GC behavior. However, the natural pheromone was about 100-fold stronger than the most purified synthetic acetate of 2S,3S,7S-diprionol in the field. As a result of various isomer combination studies, it was found that the acetate of 2S,3R,7R-diprionol, when added to 2S,3S,7S-diprionol preparation at a low concentration, increased the catch by the latter. It was therefore concluded that the above combination of the optical isomers could account for the major sex attractancy in this species.
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