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2013 , Vol. 33 >Issue 03: 542 - 550

DOI: https://doi.org/10.6023/cjoc201211018

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
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  • 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

  网络出版日期: 2012-12-18

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.

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

  • Pan Li ,
  • Chen Youwei ,
  • Liu Zhuo ,
  • Li Yonghong ,
  • Li Zhengming
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  • Research Institute of Elemento-organic Chemistry, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received date: 2012-11-08

  Revised date: 2012-12-12

  Online 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

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.

本文引用格式

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 . DOI: 10.6023/cjoc201211018

Abstract

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

参考文献

[1] Guo, W. C.; Ma, Y.; Li, Y. H.; Wang, S. H.; Li, Z. M. Acta Chim. Sinica 2009, 67, 569 (in Chinese).
(郭万成, 马翼, 李永红, 王素华, 李正名, 化学学报, 2009, 67, 569.)

[2] Xue, Y. L.; Liu, X. H.; Zhang, Y. G. Asian J. Chem. 2012, 24, 1571.

[3] Duggleby, R. G.; Pang, S. S. J. Biochem. Mol. Biol. 2000, 33, 1.

[4] Xue, Y. L.; Zhang, Y. G.; Liu, X. H. Asian J. Chem. 2012, 24, 3016.

[5] Xue, Y. L.; Zhang, Y. G.; Liu, X. H. Asian J. Chem. 2012, 24, 5087.

[6] Wang, J. G.; Ma, N.; Wang, B. L.; Wang, S. H.; Song, H. B.; Li, Z. M. Chin. J. Org. Chem. 2006, 26, 648 (in Chinese).
(王建国, 马宁, 王宝雷, 王素华, 宋海斌, 李正名, 有机化学, 2006, 26, 648.)

[7] Wang, H. X.; Li, F.; Xu, L. P.; Li, Y. H.; Wang, S. H.; Li, Z. M. Chem. J. Chin. Univ. 2010, 31, 64 (in Chinese).
(王红学, 李芳, 许丽萍, 李永红, 王素华, 李正名, 高等学校化学学报, 2010, 31, 64.)

[8] Chen, P. Q.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Asian J. Chem. 2012, 24, 2808.

[9] Wang, M. Y.; Li, Z. M.; Li, Y. H. Chin. J. Org. Chem. 2010, 30, 877 (in Chinese).
(王美怡, 李正名, 李玉新, 有机化学, 2010, 30, 877.)

[10] Ban, S. R.; Niu, C. W.; Chen, W. B.; Li, Q. S.; Xi, Z. Chin. J. Org. Chem. 2010, 30, 564 (in Chinese).
(班树荣, 牛聪伟, 陈文彬, 李青山, 席真, 有机化学, 2010, 30, 564.)

[11] Wang, M. Y.; Guo, W. C.; Lan, F.; Li, Y. H.; Li, Z. M. Chin. J. Org. Chem. 2008, 28, 649 (in Chinese).
(王美怡, 郭万成, 兰峰, 李永红, 李正名, 有机化学, 2008, 28, 649.)

[12] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 552.

[13] Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Li, B. J.; Zhao, W. G. Lett. Drug Des. Discovery 2012, 9, 431.

[14] Tong, J. Y.; Shi, Y. X.; Liu, X. H.; Sun, N. B.; Li, B. J. Chin. J. Org. Chem. 2012, 32, 2373 (in Chinese).
(童建颖, 石延霞, 刘幸海, 孙娜波, 李宝聚, 有机化学, 2012, 32, 2373.)

[15] Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Li, B. J.; Zhao, W. G. J. Heterocycl. Chem. 2013, DOI: 10.1002/jhet.1656.

[16] Lan, F.; Xu, J. Y.; Li, Y. H.; Wang, S. H.; Li, Z. M. Chem. J. Chin. Univ. 2009, 30, 712 (in Chinese).
(兰峰, 徐俊英, 李永红, 王素华, 李正名, 高等学校化学学报, 2009, 30, 712.)

[17] Wang, L.; Ma, Y.; Liu, X. H.; Li, Y. H.; Song, H. B.; Li, Z. M. Chem. Biol. Drug Des. 2009, 73, 674.

[18] Wang, L.; Tang, M.; Li, W. M.; Li, Y. H.; Wang, S. H.; Li, Z. M. Chem. J. Chin. Univ. 2008, 29, 1371 (in Chinese).
(王雷, 唐蜜, 李文明, 李永红, 王素华, 李正名, 高等学校化学学报, 2008, 29, 1371.)

[19] Weng, J. Q.; Wang, L.; Liu, X. H. J. Chem. Soc. Pakistan 2012, 34, 1248.

[20] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 558.

[21] Liu, X. F.; Liu, X. H. Acta Crystallogr. 2011, E67, O202.

[22] Liu, H. J.; Weng, J. Q.; Tan, C. X.; Liu, X. H. Acta Crystallogr. 2011, E67, O1940.

[23] Xu, Q. G.; Liu, T. Y.; Tian, R.; Ma, D. Y.; Li, Q. G. Chin. J. Org. Chem. 2008, 28, 234 (in Chinese).
(徐启贵, 刘天渝, 田睿, 马德银, 李勤耕, 有机化学, 2008, 28, 234.)

[24] Liu, X. H.; Pan, L.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Wang, B. L.; Li, Z. M. Mol. Diversity 2012, 16, 251.

[25] Liu, X. H.; Pan, L.; Tan, C. X.; Weng, J. Q.; Wang, B. L.; Li, Z. M. Pestic. Biochem. Phys. 2011, 101, 143.

[26] Liu, X. H.; Zhao, W. G.; Wang, B. L.; Li, Z. M. Res. Chem. Intermed. 2012, 38, 1999.
[27] Liu, X. H.; Pan, L.; Ma, Y.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Shi, Y. X.; Li, B. J.; Li, Z. M.; Zhang, Y. G. Chem. Biol. Drug Des. 2011, 78, 689.
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