新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究
收稿日期: 2015-08-07
修回日期: 2015-11-06
网络出版日期: 2015-11-16
基金资助
国家自然科学基金(No. 21371052)和黑龙江省博士后科研启动基金(No. LBH-Q14138)资助项目.
Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group
Received date: 2015-08-07
Revised date: 2015-11-06
Online published: 2015-11-16
Supported by
Project supported by the the National Natural Science Foundation of China (No. 21371052) and the Heilongjiang Postdoctoral Scientific Research Foundation (No. LBH-Q14138).
温彦鹏 , 张爽 , 侯广峰 , 于颖慧 , 高金胜 . 新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究[J]. 有机化学, 2016 , 36(3) : 642 -647 . DOI: 10.6023/cjoc201508008
To obtain new herbicidal candidates with novel structure and high herbicidal activities, six new pyrazol compounds based on the structure of tembotrione were designed and synthesized. The meta substituent of benzene ring and the cyclohexadione ring in the original tembotrione structure are replaced. The six target compounds were achieved with 3-chloro-2-methylaniline as the starting material after nine steps reactions, namely diazotization, acetylization, oxidation, esterization, bromization, nucleophilic substitution, chlorination and condensation reactions. All the structures of target products and their intermediates are characterized and confirmed by 1H NMR, 13C NMR, FTIR and elemental analysis. Herbicidal activity tests are also conducted for the six compounds. The results show that each compound exhibits certain herbicidal activity toward mustard, chickweed, amur foxtail, chenopodium and polypogon fugax.
Key words： pyrazol; methylsulfonyl; tembotrione; synthesis; reaction conditions; herbicidal activities
[1] Su, S.-Q. Modern Agrochem. 2002, (3), 1 (in Chinese). (苏少泉, 现代农药, 2002, (3), 1.)
[2] Beaudegnies, R.; Edmunds, A. J. F.; Fraser, T. E. M.; Hall, R. G.; Hawkes, T. R.; Mitchell G.; Schaetzer, J.; Wendeborn, S.; Wibley, J. Bioorg. Med. Chem. 2009, 17, 4134.
[3] Yang, L.; Zhang, R.-Q.; Ye, F. Modern Agrochem. 2003, (2), 1 (in Chinese). (杨丽, 张荣全, 叶非, 现代农药, 2003, (2), 1.)
[4] Yang, J.-C.; Wu, Q.; Reng, L.-H.; Liu, C.-L. Agrochemicals 2012, 51, 547 (in Chinese). (杨吉春, 吴峤, 任兰会, 刘长令, 农药, 2012, 51, 547.)
[5] Guo, S.; Yang, F.-M.; Zhang, L. Agrochemicals 2001, 40, 20 (in Chinese). (郭胜, 杨福民, 张林, 农药, 2001, 40, 20.)
[6] Cheng, Z.-Z.; Wang, Y.; Gong, K.; Wang, G-H.; Li, W.-B.; Ye, L. Agrochemicals 2013, 52, 328 (in Chinese). (程正载, 王洋, 龚凯, 王光华, 李文兵, 叶龙, 农药, 2013, 52, 328.)
[7] Zou, X.-J.; Gao, S.; Lin, C.-F.; Dong, H.; Zhang, Z.-J. Agrochemicals 2005, 44, 382 (in Chinese). (邹晓锦, 高爽, 林长福, 董海, 张宗俭, 农药, 2005, 44, 382.)
[8] Liu, Y.-X.; Zhou, B.-Q.; Chai, B.-S.; Liu, C.-L. Agrochemicals 2007, 46, 649 (in Chinese). (刘远雄, 邹本勤, 柴宝山, 刘长令, 农药, 2007, 46, 649.)
[9] Fellman, J. H. Methods Enzymol. 1987, 142, 148.
[10] Buckthal, D. J.; Roche, P. A.; Moorehead, T. J.; Forbes, B. J. R.; Hamilton, G. A. Methods Enzymol. 1987, 142, 132.
[11] Zhang, M.; Wei, J.-F.; Bai, Y.-J.; Gao, Y.; Wu, D.; Miao, Y.-Q.; Shi, Z. Chin. J. Org. Chem. 2006, 26, 207 (in Chinese). (张敏, 魏俊发, 白银娟, 高勇, 吴亚, 苗延青, 史真, 有机化学, 2006, 26, 207.)
[12] Sui, X.-F.; Yuan, J.-Y.; Zhou, M.; He, Y.-H. Chin. J. Org. Chem. 2006, 26, 1518 (in Chinese). (隋晓峰, 袁金颖, 周密, 何永洪, 有机化学, 2006, 26, 1518.)
[13] Nayak, M.; Batchu, H.; Batra, S. Tetrahedron Lett. 2012, 53, 4206.
[14] Markovic, V.; Eric, S.; Juranic, Z. D.; Stanojkovic, T.; Ljubinka, J. L.; Rankovic, B.; Kosanic, M.; Joksovic, M. D. Bioorg. Chem. 2011, 39, 18.
[15] Huang, Y. Y.; Lin, H. C.; Cheng, K. M.; Su, W. N.; Sung, K. C.; Lin, T. P.; Huang, J. J.; Lin, S. K.; Wong, F. F. Tetrahedron 2009, 65, 9592.
[16] Mei, S.-K.; Chen, Y.-Z.; Gao, Z.-C. Chin. J. Appl. Chem. 1985, 2, 8 (in Chinese). (梅盛开, 程渝祖, 高忠潮, 应用化学, 1985, 2, 8.)
[17] Cui, R.-R.; Zhang, X.-Z.; Zhang, M.-F. Shangdong Pestic. News 2009, (7), 18 (in Chinese). (崔蕊蕊, 张秀珍, 张梅凤, 山东农药信息, 2009, (7), 18.)
[18] Van Almsick, A.; Willms, L.; Auler, T.; Bieringer, H.; Rosinger, C. US 6376429, 2002 [Chem. Abstr. 2000, 132, 264966].
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