XJIPC OpenIR  > 资源化学研究室
Thesis Advisor阿吉艾克拜尔·艾萨
Degree Grantor中国科学院研究生院
Place of Conferral北京
Degree Name博士
Degree Discipline有机化学
Keyword亚洲玉米螟 性信息素 立体选择性合成 Wittig 反应 引诱效果

许多昆虫在性发育成熟以后能向体外释放具有特殊气味的微量化学物质,以引诱同种异性昆虫前来交配,具有这种特殊功能的化学物质称为昆虫性信息素。人工合成的性信息素或类似物当用来诱捕昆虫时称为昆虫性引诱剂。昆虫性引诱剂由于对环境友好,不伤害天敌,已经成为人们越来越关注的一种新型生物农药。玉米是世界上普遍种植的谷类作物之一,亚洲玉米螟严重地影响了玉米、高粱、等作物的产量和质量,因此防治该害虫势在必行。本论文在前人工作的基础上研究了亚洲玉米螟性信息素顺/反-12-十四碳烯-1-醇乙酸酯的合成方法,并对所合成的亚洲玉米螟性信息素田间应用进行了实验研究,为生物方法防治亚洲玉米螟提供了科学的理论依据。本研究主要获得如下结果:1、成功建立了合适的合成路线,优化了合成方法,以两种不同的路线合成出亚洲玉米螟性信息素。a、分别以1,12-十二碳二醇和10-羟基癸酸为起始原料,最后通过Wittig 反应合成出了目标化合物, 产率约为 31.6%和21.5%,并用红外、质谱、核磁共振等方法对重要中间体和目标产物进行了结构鉴定,结果表明目标产物为亚洲玉米螟性信息素:(顺/反)-12-十四碳烯-1-醇乙酸酯, 经气相色谱检测,含量为97.8%,顺/反(Z/E)异构体比例为:39/61。b、分别对1,12-十二碳二醇、1,10-癸二醇与氢溴酸反应条件进行了摸索,二醇单溴代反应的收率分别达到86.7%和87.5%,经气相色谱检测,含量不低于97%。c、分别以四氢呋喃和二甲基亚砜为溶剂,正丁基锂和 NaH 的二甲基亚砜钠盐作碱,在-150C~250C 下探讨了 Wittig 反应条件,最终确定了以 NaH 的二甲基亚砜钠盐作碱,二甲基亚砜和四氢呋喃作溶剂,在0oC~25o C 进行反应为最佳的反应条件。2、将所合成的化合物制成诱芯,进行田间活性试验。结果表明诱芯具有较高的引诱活性,在100μg/个诱芯剂量下对亚洲玉米螟具有较好的引诱效果。3、对亚洲玉米螟性信息素的应用技术进行了初步探讨。发现采用三角形式和直径为5-7cm 的PVC 发泡排水管式诱捕器比水盆诱捕器省时、省工、诱捕效果更好;诱捕器悬挂在玉米地外围比悬挂在地中央的诱捕效果好,并且随玉米生长过程适时调整诱捕器的高度,使诱捕器处于玉米高度的2/3 处诱捕效果最佳。以上结果表明,采用本文的合成路线成功地合成出了亚洲玉米螟性信息素,并确定了基本的应用技术,为田间大范围防治提供了依据。

Other Abstract

Many insects can release trace compounds with special smell when their sex glands grow maturity in order to attract opposite sex adult to copulate. These compounds with peculiar function are called insect pheromones. Synthesized insect pheromones or similar compounds are called sex attractant when they are used to control the pests. Sex attractants have become one of the new bio-pesticide, which are concerned by more and more people, because they do not pollute environment and bring no harms to people and other animals. Corn is one of the cereal crops which is widely grown in the world, While Asia corn borer does badly harm to the yield and quality of the corn 、the sorghum and so on. So it is imperative to prevent and cure this pest. This paper has discussed the methods of synthesis the sex pheromone of Asia corn borer on the basis of other researchers, and also primarily studied the application of the synthesized sex pheromone in fields in order to provide a basis for further theoretical study to control the pest with bio-method. The main results and conclusion are as follows: 1、Successfully established suitable synthetic routes, optimized the synthetic methods, provided two different synthetic routes of the sex pheromones of Asia corn borer as the following: a、The target molecular(TM)was synthesized with the raw materials of 1, 12-Dodecanediol and 10-Hydroxydecanoic acid respectively via the Scholer Wittig reaction. The overall yield ratios were about 31.6% and 21.5% respectively. and the key intermediates and the target compounds obtained in this paper were identified by NMR,MS , IR etc. The result showed that the TM was the sex pheromone of Asia corn borer (Z/E)-12-tetradecene-1-ol acetate. The GC analysis results indicated that the TM is a mixture of Z / E (at the ratio of 39:61) with content of 97.5% higher. b、The reaction conditions among 1,10-Decanediol and 1,12-Dodecanediol with HBr were investigated .The yield ratio of the singular bromization were respectively up to 86.7% and 87.5%,with the content about 97% higher detected by GC. c、In the process of the Wittig reaction, the coupling reacton was carried out in n-BuLi in THF, n-BuLi in DMSO, NaH in DMSO, NaH in THF and DMSO at the temperature of -15oC~25oC respectively to find a optimum condition. The result showed that the yield is higher in NaH in THF and DMSO at the temperature of 0oC~25oC. 2、The synthesized sex pheromone carried by natural rubber baits was investigated its biological activity under dosages of 50, 100, 200,400 and 600μg in every bait. The results showed that the sex pheromone has the better attractive activity than other dosages when its dosage is 100μg / every bait. 3、The applied technologies of the synthesized sex pheromone in field traps have also been investigated. The triangle traps and PVC blowing up pipe traps are superior to pot traps with less time and work and better trapping effect. The traps placed in the outside of the corn field were superior to that in the middle. At the right moment adjusts the trap along with the corn growth process to be in corn height 2/3 to get better attractive effect. The above results showed that the synthesis route was successful in this paper, and the synthesized sex pheromone of Asia corn borer has better attractive effect in field. and the basic applied technologies were determined . All these provided clues to the field prevention and cure in a larger scale.

Document Type学位论文
Recommended Citation
GB/T 7714
李久明. 亚洲玉米螟性信息素的合成及应用研究[D]. 北京. 中国科学院研究生院,2008.
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