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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 713-717. 上一篇    下一篇

研究简报

含氮五元杂环酮的拟除虫菊酯的合成、结构和生物活性

孙娜波*,a，沈德隆b，谭成侠b，翁建全b，丛杉b，傅昊b   

  1. (a浙江树人大学生环学院 杭州 310015)
    (b浙江工业大学化学工程与材料学院 杭州 310032)
  • 收稿日期:2006-12-11 修回日期:2007-06-20 发布日期:2008-04-17
  • 通讯作者: 孙娜波

Synthesis, Structure and Biological Activities of Pyrethroids with Ni-trogen Containing Five-Membered Heterocyclic Ketone Moieties

SUN Na-Bo*,a,SHEN De-Longb,TAN Cheng-Xiab,WENG Jian-Quanb
CONG Shanb,FU Haob   

  1. (a College of Biological and Environmental Engineering, Zhejiang Shuren University, Hang-zhou 310015)
    (b College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032)
  • Received:2006-12-11 Revised:2007-06-20 Published:2008-04-17
  • Contact: SUN Na-Bo

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803

被引次数

8

以1-对乙氧基-2,2-二氯环丙烷甲酸(1a)和3-(2-氯-3,3,3-三氟-1-丙烯)-2,2-二甲基环丙烷甲酸(1b)为原料, 经酰氯化反应得到酰氯, 再以三乙胺为缚酸剂, 分别与2-烷酮、2-噻唑烷酮、2-噻唑硫酮、1-乙酰基-2-咪唑烷酮、1-甲磺酰 基-2-咪唑烷酮反应, 得到10个新的含氮五元杂环酮的拟除虫菊酯. 化合物结构经1H NMR, IR, MS和元素分析进行表征. 并用X-ray单晶衍射测定了化合物3-(1-对乙氧基-2,2-二氯环丙烷甲酰)-2-噁唑烷酮(4a-1)的晶体结构. 对合成的化合物进行了初步的生物活性测试, 结果表明, 在试验浓度下部分目标化合物对黄瓜灰霉病菌具有一定得防效作用; 其中, 化合物(4a-1)和3-(3-(2-氯-3,3,3-三氟-1-丙烯)-2,2-二甲基环丙烷甲酰)-2-噻唑烷酮(4b-3)对粘虫也分别有50%及90%的杀虫活性.

关键词: 拟除虫菊酯, 含氮五元杂环酮, 生物活性, 合成, 结构

Ten new pyrethroids with nitrogen containing five-membered heterocyclic ketone moieties were synthesized by the reaction of 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (1a) or 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane-1-carboxylic acid (1b), with thionyl chloride, and then condensation reaction with 2-oxazolidinone, 2-thiazolidinethione, 2-thiazolidinone, 1-acetylimidazolidin-2-one and 1-(methylsulfonyl)imidazolidin-2-one respectively in the presence of triethylamine. Their structures were confirmed by 1H NMR, IR, Mass Spectra and elemental analysis. The crystal structure of 3-(1-(4-ethoxyphenyl)-2,2-dichlorocyclopropylcarbonyl)oxazolidin-2-one (4a-1) was determined by X-ray diffraction analysis. The preliminary bioassay showed that some of the compounds exhibited certain fungicidal activities against Botrytis cinerea, 4a-1 and 3-(3-(2-chloro-3,3,3-trifluoro- prop-1-enyl)-2,2-dimethylcyclopropylcarbonyl)thiazolidin-2-one (4b-3) exhibited 50% and 90% in-hibition activities against Mythimnaseparate respectively.

Key words: nitrogen containing five-membered heterocyclic ketone, pyrethroid, synthesis, biological activity, structure