3-(5′-乙氧基-1,3,4-噻二唑-2′-亚甲氨基)-2-氰基-3-取代-丙烯酸酯类化合物的合成、晶体结构及生物活性

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (4): 708.

3-(5′-乙氧基-1,3,4-噻二唑-2′-亚甲氨基)-2-氰基-3-取代-丙烯酸酯类化合物的合成、晶体结构及生物活性

王婷婷, 邴贵芳, 张欣, 秦振芳, 于海波, 秦雪, 戴红, 方建新

南开大学元素有机化学国家重点实验室, 天津市农药科学重点实验室, 天津 300071

收稿日期:2009-05-31 出版日期:2010-04-10 发布日期:2010-04-10
通讯作者: 方建新, 男, 教授, 主要从事新农药创制和有机合成方面的研究. E-mail: yssfjx@yahoo.com.cn
基金资助:
国家自然科学基金(批准号: 20772068)资助.

Synthesis, Crystal Structure and Bioactivities of 2-Cyanoacrylates Containing 5-Ethoxy-1,3,4-thiadiazol-2-methylamine Moiety

WANG Ting-Ting, BING Gui-Fang, ZHANG Xin, QIN Zhen-Fang, YU Hai-Bo, QIN Xue, DAI Hong, FANG Jian-Xin*

State Key Laboratory of Elemento-Organic Chemistry, Tianjin Key Laboratory of Pesticide Science, Nankai University, Tianjin 300071, China

Received:2009-05-31 Online:2010-04-10 Published:2010-04-10
Contact: FANG Jian-Xin. E-mail: yssfjx@yahoo.com.cn
Supported by:
国家自然科学基金(批准号: 20772068)资助.

摘要/Abstract

摘要：

采用氰基丙烯酸酯与5-乙氧基-1,3,4-噻二唑-2-甲氨在乙醇中加热回流的方法合成了一系列3-(5′-乙氧基-1,3,4-噻二唑-2′-亚甲氨基)-2-氰基-3-取代-丙烯酸酯类化合物. 目标化合物结构均经¹H NMR和元素分析确证. 生物活性测试结果表明, 部分化合物对双子叶杂草油菜和苋菜显示出较好的除草活性及良好的选择性, 用化合物6j在600 g/ha剂量下对油菜和苋菜茎叶进行处理, 抑制率仍达100%和95.2%, 与对照样B相当; 氰基丙烯酸酯3位取代基体积对除草活性影响较大, 3位为异丙基时活性最高.

关键词: 5-乙氧基-1,3,4-噻二唑-2-甲氨; 氰基丙烯酸酯; 除草活性

Abstract:

Herbicidal activity of cyanoacrylates has been the subject of intense interest for the past decades. A detailed study revealed that cyanoacrylates are inhibitors of photosystemⅡ(PSⅡ) electron transportation. In this paper, a series of novel 2-cyanoacrylates containing 5-ethoxy-1,3,4-thiadiazol-2-methylamine moiety were synthesized from 5-ethoxy-1,3,4-thiadiazol-2-methanamine and 2-cyanoacrylates in refluxing ethanol. Their structures were confirmed by ¹H NMR and elemental analysis. Biological activity tests showed that some compounds exhibited good herbicidal activities and excellent selectivity against dicotyledonous weeds such as rape and amaranth pigweed. Compound 6j show the highest herbicidal activity at the dose of 600 g/ha with 100% and 95.2% inhibition activity against rape and amaranth pigweed in postemergency treatment. It show the same herbicidal level as the contrast compound B. A appropriate size group at the 3-position of acrylates is essential for high herbicidal activity. 2-Cyanoacrylates containing 5-ethoxy-1,3,4-thiadiazol-2-methylamine moiety have the research potency, further study is underway.

Key words: 5-Ethoxy-1,3,4-thiadiazol-2-methylamine; Cyanoacrylate; Herbicidal activity

TrendMD:

王婷婷, 邴贵芳, 张欣, 秦振芳, 于海波, 秦雪, 戴红, 方建新. 3-(5′-乙氧基-1,3,4-噻二唑-2′-亚甲氨基)-2-氰基-3-取代-丙烯酸酯类化合物的合成、晶体结构及生物活性. 高等学校化学学报, 2010, 31(4): 708.

WANG Ting-Ting, BING Gui-Fang, ZHANG Xin, QIN Zhen-Fang, YU Hai-Bo, QIN Xue, .... Synthesis, Crystal Structure and Bioactivities of 2-Cyanoacrylates Containing 5-Ethoxy-1,3,4-thiadiazol-2-methylamine Moiety. Chem. J. Chinese Universities, 2010, 31(4): 708.

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