Citation: Ma Hongli, Yan Xiaojing, Xiao Yumei, Yuan Dekai, Zhang Zhenhua, Fu Bin, Yuan Huizhu. Synthesis and Fungicidal Activities of Azaindolyl Thiazoline Compounds[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 158-164. doi: 10.6023/cjoc201507009 shu

Synthesis and Fungicidal Activities of Azaindolyl Thiazoline Compounds

  • Corresponding author: Fu Bin, fubinchem@cau.edu.cn
  • Received Date: 12 July 2015
    Revised Date: 19 August 2015

    Fund Project: the National Natural Science Foundation of China 21172255Project supported by the National S & T Pillar Program of China 2011BAE06B02

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  • In order to find new agrochemical products with high activities, 20 azaindolyl thiazoline compounds were designed and synthesized, and their structures were identified by spectral methods. At the concentration of 50 mg/L, some of the title compounds showed good fungicidal activities. Among those compounds, the EC50 values of 2a and 2d against Phomopsis asparagi and Pyricularia oryzae Cav are 6.55 and 9.66 mg/L, which are superior or comparable to the control pesticides, then they can serve as the lead compounds for new fungicide discovery.
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    1. [1]

      Maryanoff, B. E. Acc. Chem. Res. 2006, 39, 831.
      (b) Lu, H. Tonge, P. J. Acc. Chem. Res.2008, 41, 11.

    2. [2]

      Ye, N.; Neumeyer, J. L.; Baldessarini, R. J.; Zhen, X. C.; Zhang, A. Chem. Rev. 2013, 113, 123.
      (b) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem.Rev. 2010, 110, 4489.

    3. [3]

      Tan, X.; Zhou, Y.; Yao, Q. Z. World Notes Antibiot. 2010, 31, 207 (in Chinese).
      (谭雪, 周莹, 姚启正, 国外医药抗生素分册, 2010, 31, 207.)
      (b) Fan, J.-C.; Ren, A.-M.; Feng, J.-K.; Bo, D.-S. Chem. J. Chin. Univ. 2006, 27, 1091 (in Chinese).
      (范建训, 任爱民, 封继康, 薄冬生, 高等学校化学学报, 2006, 27, 1091.)
      (c) Tian, H.-B.; Yin, R.; Zhang, C.-F.; Zhang, L.; Li, J.-L.; Wang, L.-H.; Zhou, W.; Wang, X.-Y.; Guo, Z.-L. Chin. J. Med. Chem. 2002, 12, 214 (in Chinese).
      (田海滨, 尹端, 张春富, 张岚, 李俊玲, 王丽华, 周伟, 汪勇先, 郭子丽, 中国药物化学杂志, 2002, 12, 214.)

    4. [4]

      Wang, T.; Yin, Z.-W.; Zhang, Z.-X.; Bender, J. A.; Yang, Z.; Johnson, G.; Zheng Y.-Z.; Zadjura, L. M.; D'Arienzo, C. J.; Parker, D. D.; Gesenberg, C.; Yamanaka, G. A.; Gong, Y.-F.; Ho, H.-T.; Fang, H.; Zhou, N.-N.; McAuliffe, B. V.; Eggers, B. J.; Fan, L.; Nowicka-Sans, B.; Dicker, I. B.; Gao, Q.; Colonno, R. J.; Lin, P.-F.; Meanwell, N. A.; Kadow, J. F. J. Med. Chem. 2009, 52, 7778.
      (b) Choi-Sledeski, Y. M.; Kearney, R.; Poli, G.; Pauls, H.; Gardner, C.; Gong, Y.; Becker, M.; Davis, R.; Spada, A.; Liang, G. -Y.; Chu, V.; Brown, K.; Collussi, D.; Leadley, R., Jr.; Rebello, S.; Moxey, P.; Morgan, S.; Bentley, R.; Kasiewski, C.; Maignan, S.; Guilloteau, J.-P.; Mikol, V. J. Med. Chem. 2003, 46, 681.
      (c) Riether, D.; Harcken, C.; Razavi, H.; Kuzmich, D.; Gilmore, T.; Bentzien, J.; Pack, E. J. Jr.; Souza, D.; Nelson, R. M.; Kukulka, A.; Fadra, T. N.; Zuvela-Jelaska, L.; Pelletier, J.; Dinallo, R.; Panzenbeck, M.; Torcellini, C.; Nabozny, G. H.; Thomson, D. S. J. Med. Chem. 2010, 53, 6681.
      (d) Ganser, C.; Lauermann, E.; Maderer, A.; Stauder, T.; Kramb, J.-P.; Plutizki, S.; Kindler, T.; Moehler, M.; Dannhardt, G. J. Med.Chem. 2012, 55, 9531.
      (e) Gourdain, S.; Dairou, J.; Denhez, C.; Bui, L. C.; Rodrigues-Lima, F.; Janel, N.; Delabar, J. M.; Cariou, K.; Dodd, R. H. J. Med. Chem. 2013, 56, 9569.

    5. [5]

      Zhu, Y.-Q.; Wang, D.-Y.; Yuan, Y.-W.; Ma, Y.; Zou, X.-M.; Yang, H.-Zh. Chin. J. Org. Chem. 2012, 32, 2115 (in Chinese).
      (朱有全, 王丹阳, 袁燕伟, 马原, 邹小毛, 杨华铮, 有机化学, 2012, 32, 2115.)
      (b) Dai, H.; Miao, W.-K.; Liu, J.-B.; Wu, S.-S.; Qin, X.; Zhang, X.; Fang, J.-X. Chin. J. Org. Chem. 2012, 32, 1327 (in Chinese).
      (戴红, 苗文科, 刘建兵, 吴珊珊, 秦雪, 张欣, 方建新, 有机化学, 2012, 32, 1327.)
      (c) Dai, H.; Miao, W.-K.; Liu, J.-B.; Wu, S.-S.; Qin, X.; Fang, J.-X. Chin. J. Org. Chem. 2012, 32, 1690 (in Chinese).
      (戴红, 苗文科, 刘建兵, 吴珊珊, 秦雪, 方建新, 有机化学, 2012, 32, 1690.)
      (d) Huang, G.; Yang, J. C.; Li, H.-C.; Zhang, J.; Liu, C.-L. Pesticides 2011, 50, 79 (in Chinese).
      (黄光, 杨吉春, 李慧超, 张静, 刘长令, 农药, 2011, 50, 79.)

    6. [6]

      Li, N.; Wei, X.; Fan, H.-T.; Bi, L.; Li, X.-Y.; Yang, S.; Hu, D. Y.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1300 (in Chinese).
       

    7. [7]

      Liu, L.; Zheng, Z.-B.; Qin, Z.-H.; Fu, B.; Yuan, H.-Z. Chin. J. Org. Chem. 2008, 28, 1841 (in Chinese).
       

    8. [8]

      Fu, B.; Qi, Q.-Q.; Lu, X.-H.; Cheng, X.-M.; Xiao, Y.-M.; Li, N. Chin. J. Org. Chem. 2008, 28, 1358 (in Chinese).
      (傅滨, 齐卿卿, 路绪红, 程学明, 肖玉梅, 李楠, 有机化学, 2008, 28, 1358.)
      (b) Lu, X.-H.; Qi, Q.-Q.; Xiao, Y. M.; Li, N.; Fu, B. Heterocycles2009, 79, 1031.

    9. [9]

      Chen, N.-C. Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, p. 161 (in Chinese).

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