新型氯虫酰胺类似杀虫剂的设计 合成与生物活性分析.docx

摘要
摘要
近些年杀虫剂发展史上的又一重要突破是作用于鱼尼丁受体的新杀虫剂的开发。邻甲酰氨基苯甲酰胺类化合物(anthranilic diamides)即为其中一种,美国 DuPont公司于2000年发现这一类作用机制独特的新型杀虫剂,它通过诱导昆虫
鱼尼丁受体(ryanodine receptor,RyR)的活化使内源钙离子库释放,进而导致昆虫死亡。氯虫酰胺(Ryna)【),pyr删)是此类化合物中第一个商品化杀虫剂,可用于防治各种鳞翅目害虫,与传统农药没有交互抗性,对目标生物具有很好的选择性, 对人畜安全。
本论文以以商品化的氯虫酰胺结构为基础,利用类似合成及活性片段拼接等分子设计方法,设计并合成了三个系列邻甲酰氨基苯甲酰胺的类似物以及两个系列新的中间体共41个未见文献报道的新化合物。合成的所有新化合物的化
学结构均已通过1H1心很、瓜、MS和HImS的确认。
通过已经构建的化合物杀虫活性筛选体系,对本论文合成的化合物进行了杀虫活性的系统测试。部分化合物对于东方粘虫(4龄幼虫)表现出较好的杀虫活性,其中一系列化合物探讨了氰基取代吡啶吡唑结构的引入以及邻苯双酰胺简化为单酰胺结构对氯虫酰胺活性的影响。
关键词:鱼尼丁受体,氯虫酰胺,杀虫活性,,邻甲酰氨基苯甲
酰胺
Abstract
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Abstract
One of the latest breakthroughs in pesticide research is the R&D of a series pounds targeting at the Ryanodine Receptor(RyR).Being one class of pounds,anthranilic diamides was discovered by DuPont in 2000,which,with its new targeting machanisms,induces the activition of Ryanodine receptor to release endogeIlouS caldum store in all uncontrolled ),r1M Was the first
pound from such class,which bears exceptional activity on a broad renge of Lepidoptera and has no cross-resistance to existing insecticides,with its extraordinary selectivity to target machenism secures its safety to humans and
other animals.
Based on the structure of Rynaxyp—and the molecular design approach,
sudl as coordination,4 1 unreported pounds,
including three series of anthranilic diamides analogues and two series of new imermediates,were designed and structures of pounds synthesized were determined by 1H NMR,IR,MS and elemental analysis or HRMS.
Bv means of the estabilshed insecticidal activity screening system,the insecticidal activities of these pounds were systematically results of the biological assay showed that some of them exhibited good insecticidal
activities against Oriental Armyworm(Mythinma separata Walker)and Culex pipiells pallens. Among which by introducing group to the Nopyridylpyraz