Citation: Lei Kang, Li Pan, Zhou Xiaoyun, Wang Shiben, Wang Xuekun, Ji Lusha, Liu Renmin, Xu Xiaohua. Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2788-2797. doi: 10.6023/cjoc202005031 shu

Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action

Lei Kang ^a,, ,
Li Pan ^a ,
Zhou Xiaoyun ^a ,
Wang Shiben ^a ,
Wang Xuekun ^a ,
Ji Lusha ^a ,
Liu Renmin ^a ,
Xu Xiaohua ^b

a.
School of Pharmacy, Liaocheng University, Liaocheng, Shandong 252000
b.
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Corresponding author: Lei Kang, leikang@lcu.edu.cn
Received Date: 13 May 2020
Revised Date: 15 June 2020
Available Online: 8 July 2020
Fund Project: the Natural Science Foundation of Shandong Province ZR2017BH037the China Postdoctoral Science Foundation 2020M671984the National Natural Science Foundation of China 81803360the National Natural Science Foundation of China 31701827the Natural Science Foundation of Shandong Province ZR2019PC041Project supported by the National Natural Science Foundation of China (Nos. 31701827, 81803360), the China Postdoctoral Science Foundation (No. 2020M671984), the Doctoral Research Startup Foundation of Liaocheng University (No. 318051647), the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University (No. CXCY2020Y179) and the Natural Science Foundation of Shandong Province (Nos. ZR2019PC041, ZR2017BH037)the Doctoral Research Startup Foundation of Liaocheng University 318051647the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University CXCY2020Y179

Figures(7)

In an effort to develop novel β-triketone herbicides containing a barbituric acid moiety, a series of 5-acylbarbituric acid derivatives were designed, synthesized, and tested for herbicidal activity. The bioassay results showed that some of the target compounds, such as 5-(2-(2-chloro-4-fluorophenoxy)-1-hydroxyethylidene)-1, 3-dimethylpyrimidine-2, 4, 6(1H, 3H, 5H)-trione (BBA-22) and 5-(2-(2-bromo-4-fluorophenoxy)-1-hydroxyethylidene)-1, 3-dimethylpyrimidine-2, 4, 6(1H, 3H, 5H)-trione (BBA-27), exhibited excellent herbicidal activity against all tested weeds at a dosage of 1500 g·ha^-1. In particular, compound BBA-22 displayed good pre-emergent herbicidal activity against Brassica campestris, Amaranthus retroflexus and Digitaria sanguinalis even at a dosage of 187.5 g·ha^-1, surpassing that of a commercial herbicide 2, 4-dichlorophenoxyacetic acid (2, 4-D). Investigation of the molecular mode of action of compound BBA-22 upon treatment of Arabidopsis thaliana as a model plant revealed that BBA-22 was degraded to the corresponding phenoxyacetic acid, which explains why the herbicidal mechanism is similar to that of auxin-type herbicides. The present study demonstrates that compound BBA-22 is a proherbicide of the corresponding phenoxyacetic acid auxin herbicide and a potential lead compound for further development of novel auxin herbicides.
- β-triketone,
- 5-acylbarbituric acid,
- synthesis,
- herbicide,
- phenoxyacetic
1. [1]
  Dumas, E.; Giraudo, M.; Goujon, E.; Halma, M.; Knhili, E.; Stauffert, M.; Batisson, I.; Besse-Hoggan, P.; Bohatier, J.; Bouchard, P.; Celle-Jeanton, H.; Costa Gomes, M.; Delbac, F.; Forano, C.; Goupil, P.; Guix, N.; Husson, P.; Ledoigt, G.; Sarraute, S. J. Hazrd. Mater. 2017, 325, 136. doi: 10.1016/j.jhazmat.2016.11.059
2. [2]
  Park, C. G.; Jang, M.; Shin, E.; Kim, J. Molecules 2017, 22, 1050.
3. [3]
  Li, X. C.; Ferreira, D.; Jacob, M. R.; Zhang, Q. F.; Khan, S. I.; ElSohly, H. N.; Nagle, D. G.; Smillie, T. J.; Khan, I. A.; Walker, L. A.; Clark, A. M. J. Am. Chem. Soc. 2004, 126, 6872.
4. [4]
  Wu, J. W.; Li, B. L.; Tang, C.; Ke, C. Q.; Zhu, N. L.; Qiu, S. X.; Ye, Y. J. Nat. Prod. 2019, 82, 1917. doi: 10.1021/acs.jnatprod.9b00064
5. [5]
  Song, J. G.; Su, J. C.; Song, Q. Y.; Huang, R. L.; Tang, W.; Hu, L. J.; Huang, X. J.; Jiang, R. W.; Li, Y. L.; Ye, W. C.; Wang, Y. Org. Lett. 2019, 21, 9579.
6. [6]
  Qin, X. J.; Liu, H.; Yu, Q.; Yan, H.; Tang, J. F.; An, L. K.; Khan, A.; Chen, Q. R.; Hao, X. J.; Liu, H. Y. Tetrahedron 2017, 73, 1803. doi: 10.1016/j.tet.2017.01.052
7. [7]
  Carroll, A. R.; Avery, V. M.; Duffy, S.; Forsterd, P. I.; Guymerd, G. P. Org. Biomol. Chem. 2013, 11, 453. doi: 10.1039/C2OB26931G
8. [8]
  Hellyer, R. O. Aust. J. Chem. 1968, 21, 2825.
9. [9]
  Killeen, D. P.; Larsen, L.; Dayan, F. E.; Gordon, K. C.; Perry, N. B.; van Klink, J. W. J. Nat. Prod. 2016, 79, 564. doi: 10.1021/acs.jnatprod.5b00968
10. [10]
  Igarashi, M.; Tetsuka, Y.; Mimura, Y.; Takahashi, A.; Tamamura, T.; Sato, K. J. Antibiot. 1993, 46, 1843. doi: 10.7164/antibiotics.46.1843
11. [11]
  Kong, L. Y.; Cui, Q.; Jin, Z.; Xu, X. H. Tetrahedron Lett. 2018, 59, 1705. doi: 10.1016/j.tetlet.2018.03.038
12. [12]
  Tagasgira, M.; Watanabe, M.; Uemitsu, N. Biosci., Biotechnol.. Biochem. 1995, 59, 740. doi: 10.1271/bbb.59.740
13. [13]
  Senadeera, S. P. D.; Lucantoni, L.; Duffy, S.; Avery, V. M.; Carroll, A. R. J. Nat. Prod. 2018, 81, 1588. doi: 10.1021/acs.jnatprod.8b00154
14. [14]
  Wang, S. Y.; Lan, X. Y.; Xiao, J. H.; Yang, J. C.; Kao, Y. T.; Chang, S. T. Phytother. Res. 2008, 22, 213. doi: 10.1002/ptr.2289
15. [15]
  Christoph, F.; Kaulfers, P. M.; Stahl-Biskup, E. Planta Med. 2001, 67, 768. doi: 10.1055/s-2001-18350
16. [16]
  van Klink, J. W.; Larsen, L.; Perry, N. B.; Weavers, R. T.; Cook, G. M. Bremer, P. J. Bioorg. Med. Chem. 2005, 13, 6651. doi: 10.1016/j.bmc.2005.07.045
17. [17]
  Cacic, M.; Trkovnik, M.; Cacic, F.; Has-Schon, E. Molecules 2006, 11, 134. doi: 10.3390/11010134
18. [18]
  Beaudegnies, R.; Edmunds, A. J. F.; Fraser, T. E. M.; Hall, R. G.; Hawkes, T. R.; Mitchell, G.; Schaetzer, J.; Wendeborn, S.; Wibley, J. Bioorg. Med. Chem. 2009, 17, 4134. doi: 10.1016/j.bmc.2009.03.015
19. [19]
  Lv, P.; Chen, Y.; Zhao, Z.; Shi, T.; Wu, X.; Xue, J.; Li, Q. X.; Hua, R. J. Agric. Food Chem. 2018, 66, 1023. doi: 10.1021/acs.jafc.7b05491
20. [20]
  Lei, K.; Sun, D.W.; Hua, X. W.; Tao, Y. Y.; Xu, X. H.; Kong, C. H. Pest Manage. Sci. 2016, 72, 1381. doi: 10.1002/ps.4164
21. [21]
  Shestak, O. P.; Novikov, V. L.; Martyyas, E. A.; Anisimov, M. M. Pharm. Chem. J. 2009, 43, 498. doi: 10.1007/s11094-009-0338-4
22. [22]
  Gilardoni, G.; Clericuzio, M.; Tosi, S.; Zanoni, G.; Vidari, G. J. Nat. Prod. 2007, 70, 137. doi: 10.1021/np060512c
23. [23]
  Christoph, F.; Kaulfers, P. M.; Stahl-Biskup, E. Planta Med. 2000, 66, 556. doi: 10.1055/s-2000-8604
24. [24]
  Khambay, B. P. S.; Beddie, D. G.; Hooper, A. M.; Simmonds, M. S. J. Tetrahedron 2003, 59, 7131. doi: 10.1016/S0040-4020(03)01095-0
25. [25]
  Li, H. B.; Li, L.; Li, J. X.; Han, T. F.; He, J. L.; Zhu, Y. Q. Pest Manage. Sci. 2018, 74, 579. doi: 10.1002/ps.4739
26. [26]
  Wang, D. W.; Lin, H. Y.; He, B.; Wu, F. X.; Chen, T.; Chen, Q.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2016, 64, 8986. doi: 10.1021/acs.jafc.6b04110
27. [27]
  Wang, D. W.; Lin, H. Y.; Cao, R. J.; Ming, Z. Z.; Chen, T.; Hao, G. F.; Yang, W. C.; Yang, G. F. Pest Manage. Sci. 2015, 71, 1122.
28. [28]
  Wang, D. W.; Lin, H. Y.; Cao, R. J.; Chen, T.; Wu, F. X.; Hao, G. F.; Chen, Q.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2015, 63, 5587. doi: 10.1021/acs.jafc.5b01530
29. [29]
  Wang, D. W.; Lin, H. Y.; Cao, R. J.; Yang, S. G.; Chen, Q.; Hao, G. F.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2014, 62, 11786. doi: 10.1021/jf5048089
30. [30]
  Palwinder Singh, S. Eur. J. Med. Chem. 2014, 74, 440. doi: 10.1016/j.ejmech.2013.12.047
31. [31]
  Singh, P.; Kaur, M.; Verma, P. Bioorg. Med. Chem. Lett. 2009, 19, 3054. doi: 10.1016/j.bmcl.2009.04.014
32. [32]
  Siddiqui, Z. N.; Musthafa, T. N. M.; Ahmad, A.; Khan, A. U. Bioorg. Med. Chem. Lett. 2011, 21, 2860. doi: 10.1016/j.bmcl.2011.03.080
33. [33]
  Yan, Q.; Cao, R. H.; Yi, W.; Chen, Z. Y.; Wen, H.; Ma, L.; Song, H. C. Eur. J. Med. Chem. 2009, 44, 4235. doi: 10.1016/j.ejmech.2009.05.023
34. [34]
  Neumann, D. M.; Cammarata, A.; Backes, G.; Palmer, G. E.; Jursic, B. S. Bioorg. Med. Chem. 2014, 22, 813. doi: 10.1016/j.bmc.2013.12.010
35. [35]
  Gao, Y.; Xie, J. S.; Tang, R. T.; Yang, K. Y.; Zhang, Y. H.; Chen, L. X.; Li, H. Bioorg. Chem. 2019, 85, 168. doi: 10.1016/j.bioorg.2018.12.018
36. [36]
  Laxmi, S. V.; Reddy, Y. T.; Kuarm, B. S.; Reddy, P. N.; Crooks, P. A.; Rajitha, B. Bioorg. Med. Chem. Lett. 2011, 21, 4329. doi: 10.1016/j.bmcl.2011.05.055
37. [37]
  Freeman-Cook, K. D.; Reiter, L. A.; Noe, M. C.; Antipas, A. S.; Danley, D. E.; Datta, K.; Downs, J. T.; Eisenbeis, S.; Eskra, J. D.; Garmene, D. J.; Greer, E. M.; Griffiths, R. J.; Guzman, R.; Hardink, J. R.; Janat, F.; Jones, C. S.; Martinelli, G. J.; Mitchella, P. G.; Yocuma, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 6529. doi: 10.1016/j.bmcl.2007.09.085
38. [38]
  Kim, S. H.; Pudzianowski, A. T.; Leavitt, K. J.; Barbosa, J.; McDonnell, P. A.; Metzler, W. J.; Rankin, B. M.; Liu, R.; Vaccaro, W.; Pitts, W. Bioorg. Med. Chem. Lett. 2005, 15, 1101. doi: 10.1016/j.bmcl.2004.12.016
39. [39]
  Cordato, D. J.; Herkes, G. K.; Mather, L. E.; Morgan, M. K. J. Clin. Neurosci. 2003, 10, 283. doi: 10.1016/S0967-5868(03)00034-1
40. [40]
  Willow, M.; Johnston, G. A. R. Int. Rev. Neurobiol. 1983, 24, 15. doi: 10.1016/S0074-7742(08)60219-6
41. [41]
  Reddy, Y. T.; Sekhar, K. R.; Sasi, N.; Reddy, P. N.; Freeman, M. L.; Crooks, P. A. Bioorg. Med. Chem. Lett. 2010, 20, 600. doi: 10.1016/j.bmcl.2009.11.082
42. [42]
  Altowyan, M. S.; Barakat, A.; Soliman, S. M.; Al-Majid, A. M.; Ali, M.; Elshaier, Y. A. M. M.; Ghabbour, H. A. J. Mol. Struct. 2019, 1175, 524. doi: 10.1016/j.molstruc.2018.07.105
43. [43]
  Haldar, M. K.; Scott, M. D.; Sule, N.; Srivastavab, D. K.; Mallik, S. Bioorg. Med. Chem. Lett. 2008, 18, 2373. doi: 10.1016/j.bmcl.2008.02.066
44. [44]
  Guerin, D. J.; Mazeas, D.; Musale, M. S.; Naguib, F. N. M.; Safarjalani, O. N. A.; Kouni, M. H.; Panzica, R. P. Bioorg. Med. Chem. Lett. 1999, 9, 1477. doi: 10.1016/S0960-894X(99)00238-3
45. [45]
  Lee, D. L.; Carter, C. G. US4797147, 1989.
46. [46]
  Lei, K.; Li, P.; Yang, X. F.; Wang, S. B.; Wang, X. K.; Hua, X. W.; Sun, B.; Ji, L. S.; Xu, X. H. J. Agric. Food Chem. 2019, 67, 10489. doi: 10.1021/acs.jafc.9b03109
47. [47]
  Lei, K.; Liu, Y.; Wang, S. B.; Sun, B.; Hua, X. W.; Xu, X. H. Chem. Res. Chin. Univ. 2019, 35, 609. doi: 10.1007/s40242-019-9029-1
48. [48]
  Li, N.; Fu, L. L.; Wang, S. B.; Liu, Y.; Lei, K.; Xu, X. H. J. Liaocheng Univ. (Nat. Sci. Ed.) 2018, 31, 53(in Chinese).
49. [49]
  Xu, C.; Zhang, Y.; Yu, Y.; Li, Y.; Wei, S. Bioelectromagnetics 2018, 39, 15. doi: 10.1002/bem.22086
50. [50]
  Song, Y. J. Integr. Plant Biol. 2014, 56, 106. doi: 10.1111/jipb.12131
51. [51]
  Scherer, G. F. E.; Zahn, M.; Callis, J.; Jones, A. M. FEBS Lett. 2007, 581, 4205. doi: 10.1016/j.febslet.2007.07.059
52. [52]
  Raghavan, C.; Ong, E. K.; Dalling, M. J.; Stevenson, T. W. Funct. Integr. Genomics 2006, 6, 60. doi: 10.1007/s10142-005-0012-1
53. [53]
  Bayramoğlu, D.; Kurtay, G.; Güllü, M. Synth. Commun. 2020, 50, 649. doi: 10.1080/00397911.2019.1705349
54. [54]
  Thinnes, C. C.; Lohans, C. T.; Abboud, M. I.; Yeh, T. L.; Tumber, A.; Nowak, R. P.; Attwood, M.; Cockman, M. E.; Oppermann, U.; Loenarz, C.; Schofield, C. J. Chem. Eur. J. 2019, 25, 2019.
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