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欧洲松叶蜂性信息素手性异构体的田间评价。

Field evaluation of chiral isomers of the sex pheromone of the european pine sawfly,Neodiprion sertifer.

机构信息

Pesticide Research Center and Department of Entomology, Michigan State University, 48824, East Lansing, Michigan.

出版信息

J Chem Ecol. 1983 Jun;9(6):673-93. doi: 10.1007/BF00988775.

DOI:10.1007/BF00988775
PMID:24407616
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.

摘要

在测试的 3,7-二甲基十五烷-2-醇(双丙醇)乙酸酯或丙酸酯的对映异构体中,2S、3S 和 7S 异构体作为合成引诱剂对吸引 N.sertifer 雄虫最有效。2S、3S 和 7R 异构体表现出较弱的活性,但其他对映异构体没有吸引力。毛细管 GC 分析表明,从雌性体提取物中的天然信息素在 GC 行为上与双丙醇的合成乙酸酯相同。然而,天然信息素在野外比最纯化的 2S、3S、7S-双丙醇的合成乙酸酯强约 100 倍。通过对各种异构体组合的研究发现,当 2S、3R、7R-双丙醇的乙酸酯以低浓度添加到 2S、3S、7S-双丙醇制剂中时,后者的捕获量增加。因此,可以得出结论,上述对映异构体的组合可以解释该物种的主要性吸引力。

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引用本文的文献

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2
Field and electroantennogram responses to sex pheromone optical isomers by monophagous jack pine sawflies (Hymenoptera: Diprionidae).单食性马尾松毛虫(膜翅目:卷叶蛾科)对性信息素光学异构体的田间和触角电位反应。
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3
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本文引用的文献

1
Field and electroantennogram responses of the red-headed pine sawfly,Neodiprion lecontei (Fitch), to optical isomers of sawfly sex pheromones.红头松叶蜂(Neodiprion lecontei (Fitch))对松叶蜂性信息素对映体的场和触角电位反应。
J Chem Ecol. 1981 Nov;7(6):1063-72. doi: 10.1007/BF00987628.
2
Field attractiveness of chirally defined synthetic attractants to males ofDiprion similis andGilpinia frutetorum.手性合成引诱剂对斜纹切梢小蠹和松纵坑切梢小蠹雄虫的引诱活性。
J Chem Ecol. 1982 Jan;8(1):301-14. doi: 10.1007/BF00984025.
3
Sex pheromone specificity in the pine sawflies: interchange of acid moieties in an ester.
两种近缘双翅目叶蜂,Neodiprion nanulus nanulus 和Neodiprion sertifer(膜翅目:叶蜂科)中光活性合成和天然信息素的野外反应和气相色谱分离。
J Chem Ecol. 1987 Jun;13(6):1395-408. doi: 10.1007/BF01012286.
4
Pheromone-dependent species recognition mechanisms betweenNeodiprion pinetum andDiprion similis on white pine.松阿扁叶蜂与华山松大小蠹间基于信息素的种间识别机制。
J Chem Ecol. 1988 Apr;14(4):1131-44. doi: 10.1007/BF01019341.
5
Field response of the pine sawflyNeodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate andtrans-perillenal.松叶蜂对乙酸双氧氟虫酯、丙酸双氧氟虫酯和反式-胡椒烯醛的控释的田间反应。
J Chem Ecol. 1992 Oct;18(10):1707-25. doi: 10.1007/BF02751097.
6
Release rates for pine sawfly pheromones from two types of dispensers and phenology of Neodiprion sertifer.两种类型的诱捕器释放松叶蜂性信息素的速率及欧洲松叶蜂的物候学
J Chem Ecol. 2001 Apr;27(4):733-45. doi: 10.1023/a:1010302002735.
7
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