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2016 , Vol. 36 >Issue 1: 185 - 190

DOI: https://doi.org/10.6023/cjoc201508028

研究简报

1-甲基-3-三氟甲基-5-取代基-1H-吡唑-4-甲醛-O-(4-三氟甲基苯甲酰基)肟的合成与生物活性研究

  • 戴红 ,
  • 李宏 ,
  • 金智超 ,
  • 刘文永 ,
  • 肖瑶 ,
  • 何海兵 ,
  • 汪清民 ,
  • 石玉军
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  • a 南通大学化学化工学院 南通 226019;
    b 南开大学元素有机化学国家重点实验室 天津 300071;
    c 南通丰田化工有限公司 南通 226005

收稿日期: 2015-08-29

  修回日期: 2015-10-08

  网络出版日期: 2015-10-23

基金资助

国家自然科学基金(Nos. 21202089, 21372135)、江苏省自然科学基金(No. BK20140425)和南通市科技计划(Nos. AS2013004, CP12013002, AS2014011)资助项目.

收起

Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes

  • Dai Hong ,
  • Li Hong ,
  • Jin Zhichao ,
  • Liu Wenyong ,
  • Xiao Yao ,
  • He Haibing ,
  • Wang Qingmin ,
  • Shi Yujun
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    c Nantong Fengtian Chemical Industry Co. Ltd, Nantong 226005

Received date: 2015-08-29

  Revised date: 2015-10-08

  Online published: 2015-10-23

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), the Natural Science Foundation of Jiangsu Province (No. BK20140425), and the Science and Technology Project Fund of Nantong City (Nos. AS2013004, CP12013002, AS2014011).

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摘要

为了从吡唑类化合物中寻找活性较高的农药先导化合物, 采用活性亚结构拼接方法, 设计合成了一系列未见文献报道的新型含三氟甲基苯甲酰肟酯结构的5-取代吡唑类衍生物. 目标化合物的结构均经1H NMR, 13C NMR, MS及元素分析确证. 初步的生物活性测试结果表明, 在测试浓度为500 μg/mL时, 大多数目标化合物表现出一定的杀蚜虫活性. 当测试浓度降为200 μg/mL时, 目标化合物5b、5c、5d、5i、5l和5n对蚜虫仍有较强的抑制作用, 其杀死率分别为90%, 90%, 80%, 80%, 80%和80%.

关键词： 三氟甲基苯甲酰基; 吡唑; 合成; 生物活性

本文引用格式

戴红 , 李宏 , 金智超 , 刘文永 , 肖瑶 , 何海兵 , 汪清民 , 石玉军 . 1-甲基-3-三氟甲基-5-取代基-1H-吡唑-4-甲醛-O-(4-三氟甲基苯甲酰基)肟的合成与生物活性研究[J]. 有机化学, 2016 , 36(1) : 185 -190 . DOI: 10.6023/cjoc201508028

Abstract

In order to find novel pesticide from pyrazole compounds, a series of new pyrazole derivatives carrying trifluoromethyl benzoyl oxime ester moiety were prepared. The structures of all the title compounds were determined by 1H NMR, 13C NMR, MS and elemental analysis. Preliminary bioassay displayed that most of the target compounds showed certain insecticidal activities at the concentration of 500 μg/mL. When the concentration was reduced to 200 μg/mL, compounds 5b, 5c, 5d, 5i, 5l and 5n were still active against Aphis craccivora with inhibitory values of 90%, 90%, 80%, 80%, 80% and 80%, respectively.

Key words： trifluoromethyl benzoyl; pyrazole; synthesis; biological activity

参考文献

[1] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[2] Lahm, G. P., Selby, T. P.; Lahm, G. P., Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[3] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[4] Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J. Am. Chem. Soc. 2010, 132, 185.
[5] Li, Y. X.; Lin, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (in Chinese). (李元祥, 林龙, 陈琼, 有机化学, 2011, 31, 306.)
[6] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
[7] Liang, Y.; He, H. W.; He, H. F.; Yang, Z. W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese). (梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.)
[8] El-Moghazy, S. M.; Barsoum, F. F.; Abdel-Rahman, H. M.; Marzouk, A. A. Med. Chem. Res. 2012, 21, 1722.
[9] Sun, N. B.; Tong, J. Y.; Wu, H. K. Chin. J. Org. Chem. 2013, 33, 101 (in Chinese). (孙娜波, 童建颖, 武宏科, 有机化学, 2013, 33, 101.)
[10] Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin, Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese). (戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[11] Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341.
[12] Guo, C. P.; Peng, Q. L.; Pan, L.; Zhang, D. M.; Chen, H. R. Chin. J. Org. Chem. 2014, 34, 2505 (in Chinese). (国翠平, 彭群龙, 潘龙, 张冬梅, 陈河如, 有机化学, 2014, 34, 2505.)
[13] Xiong, L.; Zhu, X. L.; Shen, Y. Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G. F. Eur. J. Med. Chem. 2015, 95, 424.
[14] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[15] Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Bioorg. Med. Chem. 2007, 15, 3678.
[16] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[17] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[18] Liu, C. L.; Liu, X. N.; Zhang, H.; Lei, X.; Liu, W. C.; Zhang, L. X.; Li, B.; Man, Y.; Hu, X. Z.; Li, Z. C. CN 1188764, 2000 [Chem. Abstr. 2000, 132, 176977].
[19] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 70, 1207.
[20] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[21] Lü, Q.; Lu, X. T.; Dai, M.; Liu, S. M.; Zhu, W. H.; Du, P.; Lü, L. Chin. J. Org. Chem. 2015, 35, 1260 (in Chinese). (吕强, 芦昕婷, 戴明, 刘世梦, 朱为宏, 杜葩, 吕龙, 有机化学, 2015, 35, 1260.)
[22] 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.)
[23] Wang, D.; Wei, Y.; Hao, S. H. Chin. J. Org. Chem. 2015, 35, 1691 (in Chinese). (王栋, 魏艳, 郝双红, 有机化学, 2015, 35, 1691.)
[24] Xu, Y.; Lei, P.; Ling, Y.; Wang, S. W.; Yang, X. L. Chin. J. Org. Chem. 2014, 34, 1118 (in Chinese). (徐炎, 雷鹏, 凌云, 王圣文, 杨新玲, 有机化学, 2014, 34, 1118.)
[25] Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J. Heterocycl. Chem. 1990, 27, 243.
[26] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[27] Dai, H.; Shen, Y. F.; Chen, J.; Chen, H. L.; Shen, Y. J. Acta Crystallogr. 2011, E67, o726.
[28] Dai, H.; Miao, W. K.; Wu, S. S.; Qin, X.; Fang, J. X. Acta Crystallogr. 2011, E67, o775.
[29] Hu, W. Q.; Zhu, W. G.; Chen, D. H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese). (胡伟群, 朱卫刚, 陈定花, 农药学学报, 2007, 9, 240.)

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