Citation: Qiao Lili, Wei Yan, Hao Shuanghong. Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 509-518. doi: 10.6023/cjoc201708004 shu

Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

Research Center of Agro-bionic Engineering & Technology of Shandong Province, College of Chemistry & Pharmacy, Qingdao Agricultural University, Qingdao 266109

Corresponding author: Hao Shuanghong, doublered74@sina.com
Received Date: 17 August 2017
Revised Date: 10 October 2017
Available Online: 20 February 2017
Fund Project: the National Natural Science Foundation of China 31471808Project supported by the National Natural Science Foundation of China (No. 31471808)

Figures(2)

Based on the structure of lead compound of 7-hydroxy-4-methyl-coumarin, a series of novel fluorinated amide coumarin derivatives were designed and synthesized through the principle of bioactive substructure combination. Their structures were characterized by ¹H NMR, ¹³C NMR and HRMS. N-(n-Butyryl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluo-romethyl-coumarin (f1) and N-(p-methylbenzoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f9) were further confirmed by X-ray single crystal diffraction. The results of herbicidal activity indicated that compounds f1, N-phenylacetyl-N-(m-fluorobenzyl)-6-amino-7-methyloxy-4-trifluoromethyl-coumarin (f13), N-methylacryloyl-N-(m-fluoro-benzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f5), N-(cyclopropylcarbonyl)-N-(m-fluorobenzyl)-6-amino-7-meth-oxy-4-trifluoromethyl-coumarin (f7), N-(6-chloronicotinoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-cou-marin (f20), exhibited marked inhibition against the stem growth of Digitaria sanguinalis. And f9, f7, N-(naphthalene-2-carbonyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f17) showed excellent inhibition on the stem of Chenopodium glaucum. The herbicidal activities of the compounds mentioned above were more active than the commercial herbicide acetochlor. The results of crop safety evaluation showed that compounds f1、f9 and f13 were safe to Brassica pekinensis and Brassica napus but sensitive to Triticum aestivum and Sorghum bicolor. Furthermore, N-(m-bromobenzoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f12), f7 and f9 were medium active against the mycelium of phytopathogenic fungi Botrytis cinerea. And N-(hydrocinnamoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f14) was medium active to Valsa mali.
- N-acyl-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin derivatives,
- synthesis,
- herbicidal activity,
- antifungal activity
1. [1]
  Zhou, L. M. S. Thesis, Northwest A & F University, Yangling, 2013 (in Chinese).
2. [2]
  Deshmukh, M.; Pawar, P.; Joseph, M.; Phalgune, M.; Kashalkar, U.; Deshpande, R.; Nirmala, R. Indian J. Exp. Biol. 2008, 46, 788.
3. [3]
  Liu, G. -L. Ph. D. Dissertation, Northwest A & F University, Yangling, 2016 (in Chinese).
4. [4]
  Wu M. -M. M. S. Thesis, Northwest A & F University, Yangling, 2010 (in Chinese).
5. [5]
  Wei, Y.; Yu, M. -Q.; Wang, D.; Hao, S. -H. Chin. J. Pestic. 2016, 55, 793(in Chinese).
6. [6]
  Zhang, F. -H.; Wei, Y.; Wang, D.; Song, W.; Wang, X. -G.; Hao, S. -H. Chin. J. Pestic. 2011, 50, 455(in Chinese). doi: 10.3969/j.issn.1006-0413.2011.06.022
7. [7]
  Zhang, W. -H.; Jiang, M. -G. Chin. J. Org. Chem. 2010, 30, 254(in Chinese).
8. [8]
  Yang, S. -P.; Han, L. -J.; Pan, Y.; Wang, D. -Q.; Zhou Y. -N.; Zhang, F. Sci. China-Chem. 2013, 43, 858(in Chinese).
9. [9]
  Wang, S. -X. M. S. Thesis, Jiangsu University, Zhenjiang, 2010(in Chinese).
10. [10]
  Yu, C. Strait Pharm. J. 2012, 24, 265(in Chinese).
11. [11]
  Manojkumar, P.; Kochupappyravi, T.; Subbuchettiar, G. Acta Pharm. 2009, 59, 159. doi: 10.1111/j.1600-0773.1986.tb02732.x
12. [12]
  Kalkhambkar. R. G.; Kulkarni, G. M.; Kamanavalli, C. M.; Premkumar, N.; Asdaq, S. M. B.; Sun, C. M. Eur. J. Med. Chem. 2008, 43, 2178. doi: 10.1016/j.ejmech.2007.08.007
13. [13]
  Ding, L.; Fu, Y.; Ye, F. Pestic. Sci. Admin. 2011, 9, 22(in Chinese).
14. [14]
  Liu, Q. -X.; Huang, M. -Z.; Liu, A. -P.; Nie, S. -Q.; Lei, M. -X.; Ren, Y. -G.; Pei, H.; He, L. -Y.; Hu, L.; Hu, A. -X. Chin. J. Org. Chem. 2014, 34, 118(in Chinese).
15. [15]
  Liu, B.; Dong, H. -B.; Han, J. -T.; Xu, Z. -H.; Jin, S. -H.; Wang, M. -A. Chin. J. Org. Chem. 2013, 33, 2358(in Chinese).
16. [16]
  Wang, D.; Wei, Y.; Hao, S. -H. Chin. J. Org. Chem. 2015, 35, 1691(in Chinese).
17. [17]
  Liu, Q. -L.; Li, W. -T.; Sun, J. -L. Fine Chem. Intermed. 2012, 42, 49(in Chinese).
18. [18]
  Kommi, D. N.; Kumar, D.; Bansal, R.; Chebolu, R.; Chakraborti, A. K. Green Chem. 2012, 14, 3329. doi: 10.1039/c2gc36377a
19. [19]
  Liu, H. -J. Ph. D. Dissertation, Zhejiang University, Hangzhou, 2005 (in Chinese).
20. [20]
  Tang, C. -C. ; Li, Y. -C; Chen, B. ; Yang H. -Z. ; Jin, G. -Y. Pesticide Chemistry, Nankai University, Tianjin, 1998 (in Chinese).
21. [21]
  Wang, H. -S. Monatsh. Chem. 2013, 144, 411. doi: 10.1007/s00706-012-0823-4
22. [22]
  Degrote, J.; Tyndall, S.; Wong, K. F.; Vanalstine-Parris, M. Tetrahedron Lett. 2014, 55, 6715. doi: 10.1016/j.tetlet.2014.10.025
23. [23]
  Zhang, X. -L.; Wei, Y.; Wei, N. -C.; Hao, S. -H. Chin. J. Pestic. Sci. 2013, 15, 34(in Chinese).
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