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2020 , Vol. 40 >Issue 8: 2575 - 2582

DOI: https://doi.org/10.6023/cjoc202003040

研究简报

1,2,4-三唑取代的苯甲酰胺衍生物的合成及其抑菌活性

  • 蒋振华 ,
  • 程绎南 ,
  • 申国富 ,
  • 张蒙萌 ,
  • 苏子洋 ,
  • 孙连省 ,
  • 李洪连
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  • a 河南农业大学植保学院 郑州 450002;
    b 新型农药创制与应用河南省重点实验室 郑州 450002

收稿日期: 2020-03-16

  修回日期: 2020-04-17

  网络出版日期: 2020-05-19

基金资助

国家自然科学基金（No.U1704116）和国家重点研发计划（No.2017YFD0201700）资助项目.

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Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

  • Jiang Zhenhua ,
  • Cheng Yi'nan ,
  • Shen Guofu ,
  • Zhang Mengmeng ,
  • Su Ziyang ,
  • Sun Liansheng ,
  • Li Honglian
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  • a Plant Protection College, Henan Agricultural University, Zhengzhou 450002;
    b Provincial Key Laboratory of the Discovery and Application of Novel Pesticide, Zhengzhou 450002

Received date: 2020-03-16

  Revised date: 2020-04-17

  Online published: 2020-05-19

Supported by

Project supported by the National Natural Science Foundation of China (No. U1704116) and the National Key R&D Program of China (No. 2017YFD0201700).

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摘要

设计了1，2，4-三唑苯甲酰胺衍生物的合成路线，该路线包括2，6-二氯苯腈与1，2，4-三唑的催化偶联、腈的酰胺化、酰胺重氮化水解及酸的酰胺化等步骤.采用该路线合成了14个未见文献报道的1，2，4-三唑苯甲酰胺衍生物，其结构用1H NMR、13C NMR和HRMS进行了表征；利用平皿法测试了它们对小麦全蚀病和小麦根腐病病原菌的抑制活性.结果表明，化合物2-氯-N-苯基-6-（1H-1，2，4-三唑-1基）苯甲酰胺（7i）在100 mg/L浓度下对供试小麦全蚀病病原菌抑制率达到80%，在50和25 mg/L的浓度下抑制率接近对照硅噻菌胺的水平，而对能引起小麦根腐病的假禾谷镰刀菌的抑制活性不显著.

关键词： 1,2,4-三唑苯甲酰胺衍生物; 合成; 小麦全蚀病病原菌; 抑菌活性

本文引用格式

蒋振华 , 程绎南 , 申国富 , 张蒙萌 , 苏子洋 , 孙连省 , 李洪连 . 1,2,4-三唑取代的苯甲酰胺衍生物的合成及其抑菌活性[J]. 有机化学, 2020 , 40(8) : 2575 -2582 . DOI: 10.6023/cjoc202003040

Abstract

The synthetic route of substituted 1,2,4-triazole benzamide derivatives was explored, which included several steps such as catalytic cross-coupling of 2,6-dichlorobenzonitrile with a triazole, amidation of nitrile, diazotization of amide and hydrolysis, and amidation of acid. Unreported 14 new 1,2,4-triazole benzamide derivatives were synthesized. Their chemical structures were characterized by 1H NMR, 13C NMR and HRMS. Their antifungal activities against Gaeumannomyces graminis var. tritici and Fusarium pseudocerealum were evaluated in vitro by the plate method. The results indicated that antifungal activities of compound 2-chloro-N-phenyl-6-(1H-1,2,4-triazol-1-yl)benzamide (7i) against Gaeumannomyces graminis var. tritici reached up to 80% at the concentrations of 100 mg/L, and were comparable to the control level of silthiopham at the concentrations of 50 and 25 mg/L. However, these compounds didn't show obvious antifungal activities against Fusarium pseudocerealum.

Key words： 1,2,4-triazobenzamide derivatives; synthesis; Gaeumannomyces graminis var. tritici; antifungal activity

参考文献

[1] Xu, M. S.; Guo, S.; Yang, F. P.; Wang, Y.; Wu, C. H.; Jiang, X. R.; Zhao, Q. J.; Chen, W. M.; Tian, G. H.; Zhu, F. Q.; Xie, Y. C.; Hu, T. W.; Wang, Z.; He, Y.; Shen, J. S. Arch. Pharm. Chem. Life Sci. 2019, 352, e1800306.
[2] Lu, A.; Luo, H.; Shi, M.; Wu, G.; Yuan, Y.; Liu, J.; Tang, F. Bioorg. Med. Chem. Lett. 2011, 21, 4924.
[3] Zang, J.; Liang, X. W.; Huang, Y. X.; Jia, Y. P.; Li, X. Y.; Xu, W. F.; Chou, C. J.; Zhang, Y. J. J. Med. Chem. 2018, 61, 5304.
[4] Huang, L.; Lai, W. H.; Zhu, L.; Li, W.; Wei, L.; Lee, K. H.; Xie, L.; Chen, C. H. ACS Med. Chem. Lett. 2018, 9, 268.
[5] Shi, J.-J.; Ren, G.-H.; Wu, N.-J.; Liu, X.-H.; Xu, T.-M.; Tan, C.-X. Chin. J. Org. Chem. 2017, 37, 2131(in Chinese). (史建俊, 任贵华, 吴宁捷, 刘幸海, 许天明, 谭成侠, 有机化学, 2017, 37, 2131.)
[6] Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.; Li, Z. M. J. Agric. Food Chem. 2012, 60, 7565.
[7] Chen, K.; Liu, Q.; Ni, P. J.; Zhu, H. J.; Lia, Y. F.; Wang, Q. Pest Manage. Sci. 2015, 71, 1503.
[8] Wang, M.-M.; Zhang, Q.-Q.; Yue, K.; Li, Q.-S.; Xu, F.-B. Chin. J. Org. Chem. 2017, 37, 1774(in Chinese). (王梦梦, 张青青, 岳凯, 李庆山, 徐凤波, 有机化学, 2017, 37, 1774.)
[9] Lahm, G. P.; Stevenson, T. M.; Selby, T. P.; Freudenberger, J. H.; Cordova, D.; Flexner, L.; Bellin, C. A.; Dubas, C. M.; Smith, B. K.; Hughes, K. A.; Hollingshaus, J. G.; Clark, C. E.; Benner, E. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274.
[10] Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
[11] Li, W.-M; Wang, J.-G.; Li, Y.-H.; Wang, S.-H.; Li, Z.-M. Chem. J. Chin. Univ. 2010, 31, 1574(in Chinese). (李文明, 王建国, 李永红, 王素华, 李正名, 高等学校化学学报, 2010, 31, 1574.)
[12] Yang, J.-C.; Zhang, J.-B.; Chai, B.-S.; Liu, C.-L. Agrochemicals 2008, 47, 6(in Chinese). (杨吉春, 张金波, 柴宝山, 刘长令, 农药, 2008, 47, 6.)
[13] Eicken, K.; Goetz, N.; Harreus, A.; Ammermann, E.; Lorenz, G.; Rang, H. EP 545099, 1993[Chem. Abstr. 1993, 119, 160132].
[14] Moradi, W. A.; Schlegel, G.; Schnatterer, A.; Volz, F. WO 2016173998, 2016[Chem. Abstr. 2016, 165, 571164].
[15] Yoshikawa, Y.; Tomitani, K.; Katsuta, H.; Kawashima, H.; Takahashi, T.; Inami, S.; Yanase, Y.; Takashi, A.; Shimotori, H.; Tomura, N. JP 09301974, 1997[Chem. Abstr. 1997, 128, 22908].
[16] Phillion, D.; Wong, S. C.; Shortt, B. US 5486621, 1996[Chem. Abstr. 1996, 124, 253325].
[17] Freeman, J.; Ward, E. Mol. Plant Pathol. 2004, 5, 235.
[18] Xie, G.-Y.; Jin, W.-B.; Zhao, Y.-Q.; Cheng, Y.-N.; Sun, B.-J.; Sun, S.-J.; Wang, M.-Z.; Wei, D.-D.; Li, H.-L. Chin. J. Org. Chem. 2014, 34, 1124(in Chinese). (谢桂英, 靳文波, 赵艳芹, 程绎南, 孙炳剑, 孙淑君, 汪梅子, 位丹丹, 李洪连, 有机化学, 2014, 34, 1124.)
[19] Jin, W.-B.; Xie, G.-Y.; Sun, S.-J.; Zhao, Y.-Q.; Cheng, Y.-N.; Sun, B.-J.; Li, H.-L. Chin. J. Org. Chem. 2014, 34, 2376(in Chinese). (靳文波, 谢桂英, 孙淑君, 赵艳芹, 程绎南, 孙炳剑, 李洪连, 有机化学, 2014, 34, 2376.)
[20] Banerjee, S.; Ganguly, S.; Sen, K. K. J. Adv. Pharm. Educ. Res. 2013, 3, 102.
[21] Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
[22] Hosseini-Sarvari, M.; Razmi, Z. RSC Adv. 2014, 4, 44105.
[23] Hu, S.-S.; Guo, H.-C.; Jiang, H.-J.; Zheng, R.-H. Chin. J. Appl. Chem. 2011, 28, 1179(in Chinese). (胡帅帅, 郭海昌, 蒋华江, 郑人华, 应用化学, 2011, 28, 1179.)
[24] Yang, K.; Qiu, Y. T.; Li, Z.; Wang, Z. Y.; Jiang, S. J. Org. Chem. 2011, 76, 3151.
[25] Lee, S. H.; Kim, M. J.; Lee, S. H.; Kim, J.; Park, H. J.; Lee, J. Eur. J. Med. Chem. 2011, 46, 2662.
[26] Miyamoto, H.; Ueda, H.; Otsuka, T.; Aki, S.; Tamaoka, H.; Tominaga, M.; Nakagawa, K. Chem. Pharm. Bull. 1990, 38, 2472.
[27] Tsukamoto, I.; Koshio, H.; Akamatsu, S.; Kuramochi, T.; Saitoh, C.; Yatsu, T.; Yanai-Inamura, H.; Kitada, C.; Yamamoto, E.; Sakamoto, S.; Tsukamoto, S. Bioorg. Med. Chem. 2008, 16, 9524.
[28] Jautelat, M.; Erdman, D. DE 19744706, 1999[Chem. Abstr. 1999, 130, 267441].
[29] Wang, L.; Zhang, Y.; Wang, D.; Wang, M.; Wang, Y.; Feng, J. J. Agric. Food Chem. 2018, 66, 81.
[30] Jautelat, M.; Tiemann, R.; Dutzmann, S.; Haensler, G.; Stenzel, K. DE 19528046, 1996[Chem. Abstr. 1996, 125, 114638].
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