Citation: Yang Sen, Ding Chengrong, Liu Xinghai, Weng Jianquan, Yuan Jing, Tan Chengxia. Synthesis and Herbicidal Activity of Chiral Aryloxyphenoxypropionic Amides Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3588-3593. doi: 10.6023/cjoc201905028 shu

Synthesis and Herbicidal Activity of Chiral Aryloxyphenoxypropionic Amides Compounds

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b.
College of Forestry and Biotechnology, Zhejiang Agriculture and Forestry University, Hangzhou 311300

Corresponding author: Yuan Jing, 1015251265@qq.com Tan Chengxia, tanchengxia@zjut.edu.cn
Received Date: 13 May 2019
Revised Date: 3 June 2019
Available Online: 19 December 2019
Fund Project: Project supported by the National Key R & D Program (No. 2017YFD0200507)the National Key R & D Program 2017YFD0200507

Figures(3)

In order to find pesticidal lead compounds with high herbicidal activity, a series of novel chiral aryloxyphenoxypropionic amides were designed and synthesized using the principle of active substructure combination and the technology of biological enzyme splitting. The structures of the target compounds were confirmed by ¹H NMR and HRMS. The preliminary bioassay data showed that all target compounds displayed excellent herbicidal activity and selectivity against monocotyledonous weeds. At the dosage of 150 g/ha, the target compounds showed herbicidal activity against Backmannia syzigachne, Polypogon fugax and Poa acroleuca with more than 75%. And the control effects of three compounds against Polypogon fugax Nees were 100%.
- aryloxyphenoxypropionic acids,
- herbicide,
- chirality,
- herbicidal activity,
- synthesize,
- enzyme splitting
1. [1]
  Mu, J. X.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Liu, X. H.; Li, B. J.; Sun, N. B. Molecules. 2016, 21, 68. doi: 10.3390/molecules21010068
2. [2]
  Liu, X. H.; Fang, Y. M.; Xie, F.; Zhang, R. R.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Xu, T. M.; Huang, H. Y. Pest Manage. Sci. 2017, 73, 1900. doi: 10.1002/ps.4556
3. [3]
  Wang, H.; Zhai, Z. W.; Shi, Y. X.; Tan, C. X.; Weng, J. Q.; Han, L.; Li B. J.; Liu, X. H. Lett. Drug Des. Discovery 2019, DOI: 10. 2174/1570180815666180704103047. doi: 10.2174/1570180815666180704103047
4. [4]
  Cheng, L.; Zhang, R. R.; Wu, H. K.; Xu, T. M.; Liu, X. H. Front. Chem. Sci. Eng. 2019, 13, 369. doi: 10.1007/s11705-018-1734-7
5. [5]
  Zhou, J. H.; Dai, H.; Qian, H. W.; Du, X. C, ; Mao, X. Y.; Shi, Y. J.; Feng, H.; Shi, J.; Yao, Y. Chin. J. Org. Chem. 2018, 38, 2122 (in Chinese).
6. [6]
  Liu, X. H.; Xu, X. Y.; Tan, C. X.; Weng, J. Q.; Xin, J. H.; Chen, J. Pest Manage. Sci. 2015, 71, 292. doi: 10.1002/ps.3804
7. [7]
  Liu, X. H.; Zhai, Z. W.; Xu, X. Y.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Chen, J. Bioorg. Med. Chem. Lett. 2015, 25, 5524. doi: 10.1016/j.bmcl.2015.10.064
8. [8]
  Cheng, L.; Zhao, W.; Shen, Z. H.; Xu, T. M.; Wu, H. K.; Peng, W. L.; Liu, X. H. Lett. Drug Des. Discovery 2019, 16, 29.
9. [9]
  Fang, Y. M.; Zhang, R. R.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Xu, T. M.; Liu, X. H. Huang, H. Y.; Wu, H. K. Lett. Drug Des. Discovery 2018, 15, 1314. doi: 10.2174/1570180815666180313121735
10. [10]
  Liu, X. H.; Wang, Q.; Sun, Z. H.; Wedge, D. E.; Becnel, J.-J.; Estep, A. S.; Tan, C. X.; Weng, J. Q. Pest Manage. Sci. 2017, 73, 953. doi: 10.1002/ps.4370
11. [11]
  Shen, Z. H.; Sun, Z. H.; Becnel, J.-J.; Estep, A.; Wedge, D. E.; Tan, C. X.; Weng, J. Q.; Han, L, Liu. X. H. Lett. Drug Des. Discovery 2018, 15, 951. doi: 10.2174/1570180815666180102141640
12. [12]
  Shi, Y. J.; Zhou, Q.; Wang, Y.; Qian, H. W.; Ye, Y. L.; Feng, X.; Chen, H.; Li, Y. T.; Dai, H.; Wei, Z. H.; Wu, J. M. Chin. J. Org. Chem. 2018, 38, 2450 (in Chinese).
13. [13]
  Li, Z. F.; Luo, F. Y. Chin. J. Org. Chem. 2001, 21, 317 (in Chinese).
14. [14]
  Bao, W. J.; Wu, Y. G.; Mao, C. H.; Chen, M.; Huang, M. Z. Fine Chem. Intermed. 2007, 37, 1009 (in Chinese).
15. [15]
  Rendina, A. R.; Felts, J. M.; Beaudoin, J. D.; Craig-Kennard, A. C.; Look, L.-L.; Paraskos, S. L.; Hagenah, J. A. Arch. Biochem. Biophys. 1988, 265, 219. doi: 10.1016/0003-9861(88)90387-6
16. [16]
  Smith, A. E. J. Agric. Food Chem. 1977, 25, 893. doi: 10.1021/jf60212a020
17. [17]
  Walker, K. A.; Ridley, S. M.; Harwood, J. L. Biochem. J. 1988, 254, 811. doi: 10.1042/bj2540811
18. [18]
  Song, L. Y.; Hua, R. M.; Zhao, Y. C. J. Hazard. Mater. 2005, 118, 247. doi: 10.1016/j.jhazmat.2004.10.020
19. [19]
  Zhao, W.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Front. Chem. Sci. Eng. 2017, 11, 363. doi: 10.1007/s11705-016-1595-x
20. [20]
  Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, 54, 1751. doi: 10.1002/jhet.2753
21. [21]
  Cheng, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng, W. L.; Liu. X. H. J. Heterocycl. Chem. 2018, 55, 946. doi: 10.1002/jhet.3123
22. [22]
  Zhao, W.; Shen, Z. H.; Xing, J. H.; Yang, G.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chem. Pap. 2017, 71, 921. doi: 10.1007/s11696-016-0012-8
23. [23]
  Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chin. J. Struct. Chem. 2017, 36, 423.
24. [24]
  Liu, X. H.; Qiao, L.; Zhai, Z. W.; Cai, P.-P.; Cantrell, C. L.; Tan, C. X.; Weng, J. Q.; Han, L.; Wu, H. K. Pest Manage. Sci. 2019, 75, 2892.. doi: 10.1002/ps.5463
25. [25]
  Sun, N. B.; Shi, Y. X.; Liu, X. H.; Ma, Y.; Tan, C. X.; Weng, J. Q.; Jin, J. Z.; Li, B. J. Int. J. Mol. Sci. 2013, 14, 21741. doi: 10.3390/ijms141121741
26. [26]
  Zhang, J, H.; Niu, L. Z.; Li, Y.; Liu, S.; Jiang, L. Chin. J. Org. Chem. 2018, 38, 1842 (in Chinese).
27. [27]
  Liu, X. H.; Weng, J. Q.; Wang, B. L.; Li, Y. H.; Tan, C. X.; Li, Z. M. Res. Chem. Intermed. 2014, 40, 2605. doi: 10.1007/s11164-013-1113-4
28. [28]
  Che, C. L.; Hu, Y. M.; Ding, S.-S.; Xiao, Y. M.; Li, J. Q.; Qin, Z. H. Chin. J. Org. Chem. 2019, 39, 419 (in Chinese).
29. [29]
  Moon, J. K.; Keum, Y. S.; Hwang, E. C.; Park, B. S.; Chang, H. R.; Li, Q. X.; Kim, J. H. J. Agric. Food Chem. 2007, 55, 5416. doi: 10.1021/jf070358f
30. [30]
  Yu, Z. H.; Shi, D. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2316. doi: 10.1080/10426501003598663
31. [31]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626. doi: 10.1016/j.bmcl.2016.06.004
32. [32]
  Asad, M. A. U.; Lavoie, M.; Song, H.; Jin, Y. J.; Fu, Z. W.; Qian, H. F. Sci. Total Environ. 2017, 580, 1287. doi: 10.1016/j.scitotenv.2016.12.092
33. [33]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881. doi: 10.1016/j.ejmech.2016.10.017
34. [34]
  Schurter, R. US 4713109, 1988 [Chem. Abstr. 1988, 109, 128841].
35. [35]
  Kim, D. W. WO 2000005956, 2000 [Chem. Abstr. 2000, 132, 118794].
36. [36]
  Zheng, J. Y.; Wu, J. Y.; Zhang, Y. J.; Wang, Z. J. Mol. Catal. B: Enzym. 2013, 97, 62. doi: 10.1016/j.molcatb.2013.07.016
37. [37]
  Kourist, R.; Pablo, D. D. M.; Miyamoto, K. Green Chem. 2011, 13, 2607. doi: 10.1039/c1gc15162b
38. [38]
  Erdemir, S.; Yilmaz, M. J. Inclusion Phenom. Macrocyclic Chem. 2012, 72, 189. doi: 10.1007/s10847-011-9962-1
39. [39]
  Telschow, J. E. US 4614814, 1989 [Chem. Abstr. 1989, 111, 57259].
40. [40]
  Han, C. P.; Sun, J.; Huang, T. H. Chem. Reag. 2015, 37, 354 (in Chinese).
41. [41]
  Zhang, P. F.; Zhong, H.; Villain, F. US 20050240049, 2005 [Chem. Abstr. 2005, 143, 422130].
42. [42]
  Sobotka, H.; Austin, J. J. Am. Chem. Soc. 1952, 74, 3813. doi: 10.1021/ja01135a028
43. [43]
  Shen, Y. C.; Li, Y. X.; Wang, P. Chin. J. Synth. Chem. 2006, 14, 398 (in Chinese).
44. [44]
  Sugata, R.; Shashi, B. S. J. Environ. Sci. Health, Part B 2005, 40, 525. doi: 10.1081/PFC-200061518
45. [45]
  Sun, Z. H.; Huang, W.; Gong, Y.-Y.; Lan, J.; Liu, X. H.; Weng, J. Q.; Li, Y. S.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 2612 (in Chinese).
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