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(R(*),S(*))-5-羟基-4-甲基-3-庚酮,是水稻象甲(Sitophilus oryzae (L.))和玉米象(S. zeamais motsch.)雄虫产生的聚集信息素。

(R (*),S (*))-5-hydroxy-4-methyl-3-heptanone male-produced aggregation pheromone ofSitophilus oryzae (L.) andS. zeamais motsch.

机构信息

Stored Products and Household Insects Laboratory ARS-USDA, Department of Entomology, University of Wisconsin-Madison, 53706, Madison, Wisconsin.

出版信息

J Chem Ecol. 1985 Sep;11(9):1263-74. doi: 10.1007/BF01024114.

DOI:10.1007/BF01024114
PMID:24310388
Abstract

A male-produced aggregation pheromone, common to the rice weevil,Sitophilus oryzae, and the maize weevil,S. zeamais, was isolated and identified from hexane extracts of highly absorbent paper disks exposed individually to young virgin male weevils. A combination of preparative column and gas-liquid chromatography of disk extracts yielded purified natural pheromone. When analyzed by nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry, the structure of the natural pheromone, "sitophilure," proved to be (R (),S ())-5-hydroxy-4-methyl-3-heptanone, of unknown enantiomeric composition. Synthetic racemic pheromone was highly attractive to males and females of both rice and maize weevils. In addition, both sexes of the granary weevil,S. granarius (L.) were attracted to the racemic preparation.

摘要

一种雄性产生的聚集信息素,在水稻象鼻虫(Sitophilus oryzae)和玉米象鼻虫(S. zeamais)中普遍存在,从单独暴露于年轻处女雄性象鼻虫的高吸收性滤纸盘的己烷提取物中分离和鉴定出来。磁盘提取物的制备柱和气相色谱的组合分离出了纯化的天然信息素。当通过核磁共振波谱法和气相色谱-质谱法分析时,天然信息素“sitophilure”的结构被证明为(R(),S())-5-羟基-4-甲基-3-庚酮,其对映体组成未知。合成外消旋信息素对水稻象鼻虫和玉米象鼻虫的雌雄两性均具有很强的吸引力。此外,谷象(S. granarius(L.))的雌雄两性也被外消旋制剂所吸引。

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本文引用的文献

1
Aggregation pheromone of the male granary weevil,Sitophilus granarius (L.).雄米象聚集信息素,Sitophilus granarius(L.)。
J Chem Ecol. 1982 Apr;8(4):679-87. doi: 10.1007/BF00988309.
2
Male-produced aggregation pheromone of the maize weevil,Sitophilus zeamais, and interspecific attraction between threeSitophilus species.玉米象雄虫聚集信息素及其三种近缘种间的种间吸引
J Chem Ecol. 1983 Jul;9(7):831-41. doi: 10.1007/BF00987808.
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Synthesis and absolute configuration of multistriatin.多纹菌素的合成与绝对构型
象甲(鞘翅目:象甲科)的聚集信息素:鉴定进展及在基于半化学物质的害虫管理策略中的潜在应用。
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Spatial distribution and losses by grain destroying insects in transgenic corn expressing the toxin Cry1Ab.转 Cry1Ab 毒素基因玉米对蛀食性昆虫的空间分布与损失的影响
PLoS One. 2018 Aug 10;13(8):e0201201. doi: 10.1371/journal.pone.0201201. eCollection 2018.
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Aggregation Pheromone of the Bearded Weevil, Rhinostomus barbirostris (Coleoptera: Curculionidae): Identification, Synthesis, Absolute Configuration and Bioactivity.髭毛象甲(Rhinostomus barbirostris)(鞘翅目:象甲科)的聚集信息素:鉴定、合成、绝对构型及生物活性
J Chem Ecol. 2018 May;44(5):463-470. doi: 10.1007/s10886-018-0957-x. Epub 2018 Apr 16.
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Determination of chirality in 5-hydroxy-4-methyl-3-heptanone, the aggregation pheromone ofSitophilus oryzae (L.) andS. zeamais Motschulsky.测定 5-羟基-4-甲基-3-庚酮的手性,5-羟基-4-甲基-3-庚酮是水稻象甲和玉米象的聚集信息素。
J Chem Ecol. 1987 Dec;13(12):2159-69. doi: 10.1007/BF01012564.
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Male-produced aggregation pheromone of the american palm weevil,Rhynchophorus palmarum (L.) (Coleoptera, Curculionidae): Collection, identification, electrophysiogical activity, and laboratory bioassay.美洲棕榈象雄虫聚集信息素的收集、鉴定、电生理活性和实验室生物测定。
J Chem Ecol. 1991 Nov;17(11):2127-41. doi: 10.1007/BF00987996.
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Behavioral responses to food volatiles by two species of stored-product coleoptera,Sitophilus oryzae (curculionidae) andTribolium castaneum (tenebrionidae).两种仓储性鞘翅目昆虫,米象(象甲科)和赤拟谷盗(拟步甲科)对食物挥发物的行为反应。
J Chem Ecol. 1993 Apr;19(4):723-34. doi: 10.1007/BF00985004.
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