Synthesis, Crystal Structure and Biological Activity of 3-(2-Chloro-4-trifluoromethylphenoxy)benzoate

doi:10.6023/cjoc201301060

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1994-1998.DOI: 10.6023/cjoc201301060 Previous Articles Next Articles

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3-(2-氯-4-三氟甲基苯氧基)苯甲酸酯的合成、晶体结构及生物活性

彭浩, 高玉焦, 贺红武

华中师范大学化学学院教育部农药与化学生物学重点实验室武汉 430079

收稿日期:2013-02-25 修回日期:2013-05-04 发布日期:2013-05-08
通讯作者: 贺红武 E-mail:he1208@mail.ccnu.edu.cn
基金资助:
国家重点基础研究发展规划(973计划, No. 2010CB126100);国家自然科学基金(Nos. 21002037, 21172090);教育部创新团队(PCSIRT, No. IRT0953)资助项目

Synthesis, Crystal Structure and Biological Activity of 3-(2-Chloro-4-trifluoromethylphenoxy)benzoate

Peng Hao, Gao Yujiao, He Hongwu

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemitry, Central China Normal University, Wuhan 430079

Received:2013-02-25 Revised:2013-05-04 Published:2013-05-08
Supported by:
Project supported by the National Basic Research Program of China ((973 Program, No. 2010CB126100)), the National Natural Science Foundation of China (Nos. 21002037, 21172090) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT, No. IRT0953)

A series of new 3-(2-chloro-4-trifluoromethylphenoxy)benzoates (2) have been synthesized by the reactions of substituted phenols with intermediate 3-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride (1). The structures of compounds have been confirmed by ¹H NMR, IR, EI-MS and elemental analyses. The structure of 3-methylphenyl 3-(2-chloro-4-trifluoromethylphenoxy)benzoate (2f) has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that most of title compounds possess a moderate herbicidal activity against dicotyledonous weeds.

Key words: synthesis, diphenyl ether, herbicidal activity

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Peng Hao, Gao Yujiao, He Hongwu. Synthesis, Crystal Structure and Biological Activity of 3-(2-Chloro-4-trifluoromethylphenoxy)benzoate[J]. Chin. J. Org. Chem., 2013, 33(9): 1994-1998.

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[1] Su, S. Q. Agrochem. Res. Appl. 2011, 15, 1 (in Chinese).
(苏少泉, 农药研究与应用, 2011, 15, 1.)
[2] Li, H. B.; Zhu, Y. Q.; Song, X. W.; Niu, Z. X.; Hu, F. Z.; Liu, B.; Zou, X. M.; Yang, H. Z. Chin. J. Org. Chem. 2009, 29, 909 (in Chinese).
(李华斌, 朱有全, 宋晓薇, 牛子霞, 胡方中, 刘斌, 邹小毛, 杨华铮, 有机化学, 2009, 29, 909.)
[3] Jiang, L. L.; Zuo, Y.; Wang, Z. F.; Tan, Y.; Wu, Q. Y.; Xi, Z.; Yang, G. F. J. Agric. Food Chem. 2011, 59, 6172.
[4] Lei, B. L.; Li, J. Z.; Lu, J.; Du, J.; Liu, H. X.; Yao, X. J. J. Agric. Food Chem. 2009, 57, 9593.
[5] Vicentini, C. B.; Mares, D.; Tartari, A.; Manfrini, M.; Forlani, G. J. Agric. Food Chem. 2004, 52, 1898.
[6] Yang, R. N.; Sun, Y. A.; Jin, M. D. Pesticide 2001, 40, 7 (in Chinese).
(杨芮娜, 孙雨安, 金满斗, 农药, 2001, 40, 7.)
[7] Zhang, M.; Wang, J. X.; Duan, M.; Peng, X. G.; Huan, Z. B. Acta Phytophy. Sin. 2008, 35, 58 (in Chinese).
(张猛, 王金信, 段敏, 彭学岗, 郇志博, 植物保护学报, 2008, 35, 58.)
[8] Wang, Z. Y.; Li, J. H.; Yuan, J. Chem. Intermed. 2012, 10, 13 (in Chinese).
(王中洋, 李京海, 袁军, 化工中间体, 2012, 10, 13.)
[9] Zhang, H. B.; Shen, S. Q.; Zhou, C. H.; Tian, C. M. Zhejiang Chem. Ind. 2005, 36, 19 (in Chinese).
(张海滨, 沈书群, 周昌宏, 田昌明, 浙江化工, 2005, 36, 19.)
[10] Jiang, C. Y. Pesticide 2006, 45, 99 (in Chinese).
(江承艳, 农药, 2006, 45, 99.)
[11] Bai, Y. H.; Li, R, J.; Hong, G. F.; Tian, X. H. Modern Agrochem. 2006, 5, 12 (in Chinese).
(白延海, 李瑞军, 洪广峰, 田新慧, 现代农药, 2006, 5, 12.)
[12] Ge, F. X.; Liang, K. Anhui Chem. Ind. 2003, (2), 28 (in Chinese).
(葛发祥, 梁克俭, 安徽化工, 2003, (2), 28.)
[13] Peng, H.; Ning, L. H.; Tu, H. Y.; He, H. W. Chin. J. Appl. Chem. 2003, 20, 643 (in Chinese).
(彭浩, 宁丽红, 涂海洋, 贺红武, 应用化学, 2003, 20, 643.)
[14] Ning, L. H.; Peng, H.; Tu, H. Y.; He, H. W. Chin. J. Pestic. Sci. 2004, 6, 74 (in Chinese).
(宁丽红, 彭浩, 涂海洋, 贺红武, 农药学学报, 2004, 6, 74.)
[15] Peng, H.; He, H. W. Chin. J. Org. Chem. 2007, 27, 502 (in Chinese).
(彭浩, 贺红武, 有机化学, 2007, 27, 502.)
[16] Liu, J. C.; Cui, Z. P.; He, H. W. Chin. J. Org. Chem. 2012, 32, 1 (in Chinese).
(刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1.)

3-(2-氯-4-三氟甲基苯氧基)苯甲酸酯的合成、晶体结构及生物活性

Synthesis, Crystal Structure and Biological Activity of 3-(2-Chloro-4-trifluoromethylphenoxy)benzoate

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