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2014 , Vol. 34 >Issue 4: 774 - 782

DOI: https://doi.org/10.6023/cjoc201309004

研究论文

2-甲氧亚胺基-2-(多取代苯基)乙酸甲酯类化合物合成及杀菌活性

  • 姜文涛 ,
  • 胡方中 ,
  • 顾翰 ,
  • 刘传 ,
  • 魏乃翔 ,
  • 万蕾 ,
  • 任士钊 ,
  • 王俊婷 ,
  • 徐凤波
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  • 南开大学元素有机化学国家重点实验室 元素有机化学研究所 天津 300071

收稿日期: 2013-09-02

  修回日期: 2013-12-02

  网络出版日期: 2013-12-13

基金资助

国家“十二五”科技支撑计划（Nos. 2011BAE06B03-12，2011BAE06B05）、国家自然科学基金（No. 21172114）和天津市自然科学基金（No. 11JCYBJC14200）资助项目.

收起

Synthesis and Fungicidal Activity of Methyl 2-Methoxyimino-2-polysubstituted-phenylacetates

  • Jiang Wentao ,
  • Hu Fangzhong ,
  • Gu Han ,
  • Liu Chuan ,
  • Wei Naixiang ,
  • Wan Lei ,
  • Ren Shizhao ,
  • Wang Junting ,
  • Xu Fengbo
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  • State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received date: 2013-09-02

  Revised date: 2013-12-02

  Online published: 2013-12-13

Supported by

Project supported by the National “Twelfth Five-Year” Plan for Science & Technology Support (Nos. 2011BAE06B03-12, 2011BAE06B05), the National Natural Science Foundation of China (No. 21172114) and the Natural Science Foundation of Tianjin City (No. 11JCYBJC14200).

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摘要

以取代甲苯为原料，与草酰氯单甲酯反应生成傅克酰基化产物2-羰基-2-（邻甲基苯基）乙酸甲酯（A），A与甲氧基胺盐酸盐反应得到（Z/E）-2-（甲氧亚胺基）-2-（邻甲基苯基）乙酸甲酯（B），B与溴单质反应得到中间体（Z/E）-2-（2-溴甲基）苯 基-2-甲氧亚胺基乙酸甲酯（C）. E-2-甲氧亚胺基-（2-溴甲基苯基）乙酸甲酯（E）用硝酸硝化得到中间体E-2-甲氧亚胺基-（2-溴甲基-5-硝基苯基）乙酸甲酯（F）. 中间体C和F与芳香酮肟经过缩合反应生成甲氧亚胺基-（4或5-取代基-2-（1-（3或4-取代苯基）-E-亚乙基胺氧甲基）苯基）乙酸甲酯化合物（D，E和G），H可以从G1还原得到. 所得新化合物均通过1H NMR，13C NMR，19F NMR，IR和HRMS等确证. 用生长速率法测试了目标化合物对黄瓜灰霉、番茄早疫、小麦赤霉、辣椒疫霉、油菜菌核和水稻纹枯等6种真菌的离体抑菌活性. 结果表明，部分目标化合物比肟菌酯有更高的杀菌活性.

关键词： 甲氧基丙烯酸酯化合物; 合成; 杀菌活性

本文引用格式

姜文涛 , 胡方中 , 顾翰 , 刘传 , 魏乃翔 , 万蕾 , 任士钊 , 王俊婷 , 徐凤波 . 2-甲氧亚胺基-2-(多取代苯基)乙酸甲酯类化合物合成及杀菌活性[J]. 有机化学, 2014 , 34(4) : 774 -782 . DOI: 10.6023/cjoc201309004

Abstract

Reaction of methyl 2-chloro-2-oxacetate and 4-chlorotoluene (or 3-tert-butyltoluene) in the presence of AlCl3 in CH2Cl2 generated 2-(5-chloro-or 4-tert-butyl-toluene)-2-methyl-phenyl-2-oxoacetate (A), which were treated with O-methyl-hydroxylamine to furnish (Z/E)-methyl-2-(5-chloro (or 4-tert-butyl)-2-methyl phenyl)-2-(methoxyimino)acetates (B). B were brominated with Br2 to afford the intermediate (Z/E)-ethyl-2-(2-bromomethyl-5-chloro (or 4-tert-butyl)-2-methyl-phenyl)-2-(methoxyimino)acetates (C). The intermediate E-methyl-2-(2-(bromomethyl phenyl)-5-nitro-phenyl)-2-(methoxyimino)acetate (F) was obtained from nitration of E-methyl-2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate (E). The intermediates C and F were condensed with various aryl ketoximes to produce the title compounds (D, E and G). Compound H was obtained from the reduction of G1. All of the title compounds have been characterized by 1H NMR, 13C NMR, 19F NMR, IR and HRMS. All of the title compounds were tested for fungicidal activities against cucumber gray mold, tomato disease early, wheat gibberellic, pepper phytophthora, rape sclerotium, rice grain dry and so forth by the mycelium growth rate method, which indicated that some of them displayed better fungicidal activity than that of trifloxystrobin.

Key words： methoxyl acrylate compounds; synthesis; fungicidal activity

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