Citation: Shi Yujun, Du Xianchao, Wang Xianglong, Chen Qingwen, Li Ling, Dai Hong, Xu Caiqin, Zhang Jingyuan, Ling Yong. Synthesis and Herbicidal Activity of Novel Cyanoacrylate Derivatives Containing Substituted Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1772-1778. doi: 10.6023/cjoc201802026 shu

Synthesis and Herbicidal Activity of Novel Cyanoacrylate Derivatives Containing Substituted Oxazole Moiety

Shi Yujun ^a ,
Du Xianchao ^a ,
Wang Xianglong ^a ,
Chen Qingwen ^a ,
Li Ling ^a ,
Dai Hong ^a,, ,
Xu Caiqin ^a ,
Zhang Jingyuan ^a ,
Ling Yong ^b,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019
b.
School of Pharmacy, Nantong University, Nantong 226001

Corresponding author: Dai Hong, daihong_2015@aliyun.com Ling Yong, yling2015@aliyun.com
Received Date: 26 February 2018
Revised Date: 9 March 2018
Available Online: 16 July 2018
Fund Project: the Science and Technology Innovation Foundation for the College Students of Jiangsu Province 201710304048Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), the Science and Technology Project Fund of Nantong City (No. MS22015020), and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201710304048)the National Natural Science Foundation of China 21372135the Science and Technology Project Fund of Nantong City MS22015020the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013

Figures(2)

In search of novel cyanoacrylates with potent bioactivity, a series of new cyanoacrylate derivatives containing substituted oxazole moiety were designed and synthesized through the strategy of active substructure combination. They were structurally characterized by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data showed that most title compounds possessed good herbicidal activity at the dosage of 1500 g/ha, 9 compounds exhibited herbicidal activity against Brassica juncea with 80%~100%, 12 compounds had herbicidal activity against Chenopodium serotinum L. with 80%~100%, two compounds both displayed 70% herbicidal activity against Alopecurus aequalis Sobol, and one compound showed 100%, 70%, and 60% herbicidal activity against Rumex acetosa L., Polypogon fugax Nees ex Steud and Poa acroleuca Steud, respectively. Additionally, the inhibitory rates of one compound against Brassica juncea and Rumex acetosa L.were both 30% at 37.5 g/ha.
- oxazole,
- cyanoacrylate,
- synthesis,
- herbicidal activity
1. [1]
  Liu, H. Y.; Tan, H. F.; Yang, H. Z. Chem. J. Chin. Univ. 2000, 21, 1855 (in Chinese). doi: 10.3321/j.issn:0251-0790.2000.12.037
2. [2]
  Song, B. A.; Yang, S.; Zhong, H. M.; Jin, L. H.; Hu, D. Y.; Lin, G. J. Fluorine Chem. 2005, 126, 87. doi: 10.1016/j.jfluchem.2004.10.041
3. [3]
  Ouyang, G. P.; Song, B. A.; Zhang, H. P.; Yang, S.; Jin, L. H.; Li, Q. Z.; Hu, D. Y. Molecules, 2005, 10, 1351. doi: 10.3390/10101351
4. [4]
  Liu, Y. X.; Cao, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2007, 55, 3011. doi: 10.1021/jf0636519
5. [5]
  Zhong, S. H.; Wang, C. F.; Song, Q. X.; Fan, M. L.; Liu, B. Y.; Wei, D. M.; Liu, J. B. Chin. J. Org. Chem. 2014, 34, 2324 (in Chinese).
6. [6]
  Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92 (in Chinese).
7. [7]
  Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese).
8. [8]
  Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472 (in Chinese).
9. [9]
  Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. J. Agric. Food Chem. 2003, 51, 5030. doi: 10.1021/jf034067s
10. [10]
  Song, B. A.; Zhang, H. P.; Wang, H.; Yang, S.; Jin, L. H.; Hu, D. Y.; Pang, L. L.; Xue, W. J. Agric. Food Chem. 2005, 53, 7886. doi: 10.1021/jf051050w
11. [11]
  Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849. doi: 10.1021/jf803632t
12. [12]
  Shi, Y. J.; Fang, Y.; Li, Y.; Chen, J.; Li, G.; Wang, Q. M.; Dai, H. Chem. J. Chin. Univ. 2017, 38, 421 (in Chinese). doi: 10.7503/cjcu20160510
13. [13]
  Wang, M. M.; Zhang, Q. Q.; Yue, K.; Li, Q. S.; Xu, F. B. Chin. J. Org. Chem. 2017, 37, 1774 (in Chinese).
14. [14]
  Gideens, A. C.; Boshoff, H. I. M.; Franzblau, S. G.; Barry Ⅲ, C. E.; Coppa, B. R. Tetrahedron Lett. 2005, 46, 7355. doi: 10.1016/j.tetlet.2005.08.119
15. [15]
  Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347. doi: 10.1016/j.ejmech.2014.06.001
16. [16]
  Lin, J.; Chen, J. W.; Cai, X. Y.; Qiao, X. L.; Huang, L. P.; Wang, D. G.; Wang, Z. J. Agric. Food Chem. 2007, 55, 7626. doi: 10.1021/jf071009o
17. [17]
  Wu, C.; Liang, Z. W.; Xu, Y. Y.; He, W. M.; Xiang, J. N. Chin. Chem. Lett. 2013, 24, 1064. doi: 10.1016/j.cclet.2013.06.026
18. [18]
  Zhong, Z. J.; Zhang, D. J.; Peng, Z. G.; Li, Y. H.; Shan, G. Z.; Zuo, L. M.; Wu, L. T.; Li, S. Y.; Gao, R. M.; Li, Z. R. Eur. J. Med. Chem. 2013, 69, 347.
19. [19]
  Ohnmacht, S. A.; Ciancimino, C.; Vignaroli, G.; Gunaratnam, M.; Neidle, S. Bioorg. Med. Chem. Lett. 2013, 23, 5351. doi: 10.1016/j.bmcl.2013.07.057
20. [20]
  Xiao, L. W.; Zhang, G. X.; Jing, X. M.; Zhou, Q. X.; Feng, R. Chin. J. Org. Chem. 2016, 36, 1000 (in Chinese).
21. [21]
  Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672. doi: 10.1016/j.cclet.2015.04.017
22. [22]
  Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014. doi: 10.1016/j.cclet.2014.06.011
23. [23]
  Dai, H.; Chen, J.; Hong, Yu.; Yuan, B. Y.; Chen, Y. M.; Shi, Y. J.; Ma, R. Y.; Liang, Z. P.; Shi, J. Chin. J. Org. Chem. 2017, 37, 739 (in Chinese).
24. [24]
  Dai, H.; Fang, Y.; Li, Y.; Wang, X. L.; Xiang, X. B.; Ge, S. S.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 2973 (in Chinese).
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