新型含三唑啉酮的磺酰脲类化合物的合成、晶体结构及除草活性研究

doi:10.6023/cjoc201211018

有机化学 ›› 2013, Vol. 33 ›› Issue (03): 542-550.DOI: 10.6023/cjoc201211018 上一篇下一篇

研究论文

新型含三唑啉酮的磺酰脲类化合物的合成、晶体结构及除草活性研究

潘里, 陈有为, 刘卓, 李永红, 李正名

南开大学元素有机化学研究所元素有机化学国家重点实验室天津 300071

收稿日期:2012-11-08 修回日期:2012-12-12 发布日期:2012-12-18
通讯作者: 李正名 E-mail:nkzml@vip.163.com
基金资助:
国家自然科学基金(No. 21272129)、国家重点基础研究发展计划(973, No. 2010CB126106)、国家科技攻关计划(No. 2011BAE06B05)资助项目.

Synthesis, Crystal Structure and Herbicidal Activity of Novel Sulfonylureas Containing Triazolinone Moiety

Pan Li, Chen Youwei, Liu Zhuo, Li Yonghong, Li Zhengming

Research Institute of Elemento-organic Chemistry, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2012-11-08 Revised:2012-12-12 Published:2012-12-18
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272129), the National Basic Research Program of China (No. 2010CB126106) and the National Key Technologies R&D Program (No. 2011BAE06B05).

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摘要/Abstract

为了进一步寻找高效的磺酰脲类除草剂, 以商品化磺酰脲类除草剂为基础, 将三唑啉酮杂环引入到分子中, 合成了23个未见文献报道的新型磺酰脲化合物, 通过¹H NMR、高分辨质谱以及X射线单晶衍射确定了其结构. 经盆栽法和平皿法测试了所有化合物的除草活性以及部分化合物对油菜的IC₅₀值. 结果表明, 化合物5h具有优秀的除草活性, 其对油菜的IC₅₀值与对照药醚苯磺隆和醚磺隆相近, 在3.75 g/ha浓度下对单子叶杂草稗草具有优异的盆栽抑制活性.

In order to search for efficient sulfonylurea herbicides, the title compounds were designed by introducing triazolinones into some known sulfonylurea structures. 23 novel sulfonylurea compounds had been synthesized and characterized by ¹H NMR, HRMS and X-ray diffraction. Herbicidal activities of title compounds were determined by pot-culture method. IC₅₀ values of some effective sulfonylurea compounds were tested by culture dish method. It was found that compound 5h attained the super-active level which was comparable to the controls as triasulfuron and cinosulfuron. It was worthy to note that compound 5h had potent inhibitory activity against Echinochloa crusgalli by pot-culture method at 3.75 g/ha.

Key words: sulfonylurea, triazolinone, synthesis, crystal structure, herbicidal activity

引用此文

潘里, 陈有为, 刘卓, 李永红, 李正名. 新型含三唑啉酮的磺酰脲类化合物的合成、晶体结构及除草活性研究[J]. 有机化学, 2013, 33(03): 542-550.

Pan Li, Chen Youwei, Liu Zhuo, Li Yonghong, Li Zhengming. Synthesis, Crystal Structure and Herbicidal Activity of Novel Sulfonylureas Containing Triazolinone Moiety[J]. Chin. J. Org. Chem., 2013, 33(03): 542-550.

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新型含三唑啉酮的磺酰脲类化合物的合成、晶体结构及除草活性研究

Synthesis, Crystal Structure and Herbicidal Activity of Novel Sulfonylureas Containing Triazolinone Moiety

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