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  • 1
    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.
    Type of Medium: Electronic Resource
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  • 2
    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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  • 3
    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.
    Type of Medium: Electronic Resource
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