Citation: Xia-Li Yue, Hu Li, Shuang-Shuang Liu, Qing-Ye Zhang, Jing-Jing Yao, Fei-Yan Wang. N-Fluorinated phenyl-N'-pyrimidyl urea derivatives：Synthesis, biological evaluation and 3D-QSAR study[J]. Chinese Chemical Letters, ;2014, 25(7): 1069-1072. doi: 10.1016/j.cclet.2014.03.046 shu

N-Fluorinated phenyl-N'-pyrimidyl urea derivatives：Synthesis, biological evaluation and 3D-QSAR study

1.
College of Science, Huazhong Agricultural University, Wuhan 430070, China

Corresponding author: Qing-Ye Zhang,
Received Date: 31 December 2013
Available Online: 17 March 2014
Fund Project: This work was supported by the National Natural Science Foundation of China (No.30900935) (No.30900935)

With the increase of herbicide-resistant weeds, novel, more selective and even more potent herbicides to control weeds are needed. In this paper, a series of N-Fluorinated phenyl-N'-pyrimidyl urea derivatives were synthesized and screened for their herbicidal activities against Amaranthus retroflexus (AR) and Setaria viridis (SV). Compound 25 (N-(3-trifluoromethylphenyl)-N'-(2-amino-4-chloro-6-methylpyrimidyl) urea) exhibited marked herbicidal activity against SV (IC₅₀=11.67 mg/L) and is more potent than bensulfuron (IC₅₀=27.45 mg/L), a commercially available herbicide. A statistically significant CoMFA model with high prediction abilities (q²=0.869, r²=0.989) was obtained.
- Fluorinated phenyl,
- Pyrimidine,
- QSAR,
- Herbicidal activities
1. [1]
  [1] H.J. Beckie, F.J. Tardif, Herbicide cross resistance in weeds, Crop Prot. 35 (2012) 15-28.
2. [2]
  [2] B. Chauvel, J.P. Guillemin, J. Gasquez, C. Gauvrit, History of chemical weeding from 1944 to 2011 in France: changes and evolution of herbicide molecules, Crop Prot. 42 (2012) 320-326.
3. [3]
  [3] C. Andreasen, H. Stryhn, J. Streibig, Decline of the flora in Danish arable fields, J. Appl. Ecol. 33 (1996) 619-626.
4. [4]
  [4] K.M. Khan, S. Saeed, M. Ali, et al., Unsymmetrically disubstituted urea derivatives: a potent class of antiglycating agents, Bioorg. Med. Chem. 17 (2009) 2447-2451.
5. [5]
  [5] P.A. Yonova, G.M. Stoilkova, Synthesis and biological activity of urea and thiourea derivatives from 2-aminoheterocyclic compounds, J. Plant Growth Regul. 23 (2004) 280-291.
6. [6]
  [6] R.H. Tale, A.H. Rodge, G.D. Hatnapure, A.P. Keche, The novel 3,4-dihydropyrimidin-2(1H)-one urea derivatives of N-aryl urea: synthesis, anti-inflammatory, antibacterial and antifungal activity evaluation, Bioorg. Med. Chem. Lett. 21 (2011) 4648-4655.
7. [7]
  [7] S.A. Khan, N. Singh, K. Saleem, Synthesis, characterization and in vitro antibacterial activity of thiourea and urea derivatives of steroids, Eur. J. Med. Chem. 43 (2008) 2272-2280.
8. [8]
  [8] J.C. Emerson, L.H. Steimel, Corrosion inhibitor composition enhanced by carbamide addition for scale removal on galvanized metal surfaces, US 20070164258, 2007.
9. [9]
  [9] J.Z. Chen, G. Ling, S.W. Lu, Synthesis of N-phenyl-N'-pyrimidylurea derivatives by selenium-or selenium dioxide-catalyzed reductive carbonylation of nitroaromatics, Eur. J. Org. Chem. (2003) 3446-3452.
10. [10]
  [10] B.E. Smart, Fluorine substituent effects (on bioactivity), J. Fluorine Chem. 109 (2001) 3-11.
11. [11]
  [11] B. Nathalie, W. Marco, E.L. Mark, et al., Structure-activity relationships in tripodal transmembrane anion transporters: the effect of fluorination, J. Am. Chem. Soc. 133 (2011) 14136-14148.
12. [12]
  [12] Y.C. Wang, Z.Y. Bai, Z.J. Wei, et al., Facile synthesis and biological evaluation of novel fluorine-containing N-nitro-N'-substituted phenylurea, Res. Chem. Intermed. 37 (2011) 1029-1039.
13. [13]
  [13] P. Jeschke, The unique role of fluorine in the design of active ingredients for modern crop protection, ChemBioChem 5 (2004) 570-589.
14. [14]
  [14] P. Zhou, J.W. Zou, F.F. Tian, Z.C. Shang, Fluorine bonding -how does it work in protein-ligand interactions? J. Chem. Inf. Model. 49 (2009) 2344-2355.
15. [15]
  [15] P. Jeschke, The unique role of halogen substituents in the design of modern agrochemicals, Pest Manag. Sci. 66 (2010) 10-27.
16. [16]
  [16] S.M.A. Hai, S. Perveen, R.A. Khan, et al., Tertiary amines promoted synthesis of symmetrical 1,3-disubstituted ureas, Nat. Prod. Res. 17 (2003) 351-354.
17. [17]
  [17] S. Perveen, S.M.A. Hai, R.A. Khan, et al., Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas, Synth. Commun. 35 (2005) 1663-1674.
18. [18]
  [18] Pesticides guidelines for laboratory bioactivity tests. Part 1: Petri dish test for herbicide bioactivity [Code: NY/T 1155.1-2006].
19. [19]
  [19] R.A. Patil, P.B. Choudhari, M.S. Bhatia, et al., 3D-QSAR study on pyrazole derivatives containing thiourea as EGFR inhibitors, Asian J. Biochem. Pharm. Res. 2 (2012) 352-366.
20. [20]
  [20] D. Kumar, A. Kapoor, A. Thangadurai, P. Kumar, B. Narasimhan, Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides, Chin. Chem. Lett. 22 (2011) 1293-1296.
21. [21]
  [21] Q.Y. Zhang, J. Wan, X. Xu, et al., Structure-based rational quest for potential novel inhibitors of human HMG-CoA reductase by combining CoMFA 3D QSAR Modeling and Virtual Screening, J. Comb. Chem. 9 (2007) 131-138.
22. [22]
  [22] Q.Y. Zhang, C. Yu, J. Min, et al., Rational questing for potential novel inhibitors of FabK from Streptococcus pneumoniae by combining FMO calculation, CoMFA 3DQSAR modeling and virtual Screening, J. Mol. Model. 17 (2011) 1483-1492.
23. [23]
  [23] R. Vijayaraj, M.L.V. Devi, V. Subramanian, P.K. Chattaraj, 3D-QSAR studies on the inhibitory activity of trimethoprim analogues against Escherichia coli dihydrofolate reductase, Chem. Biol. Drug Des. 79 (2012) 935-942.
24. [24]
  [24] M. Clark, R.D. Cramer, O.N. Van, Validation of the general purpose tripos 5.2 force field, J. Comput. Chem. 10 (1989) 982-1012.
25. [25]
  [25] B.L. Bush, R.B. Nachbar, Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA, J. Comput. Aided Mol. Des. 7 (1993) 587-619.
26. [26]
  [26] J.H. Jiang, X.F. Liu, C.H. Zhen, et al., Acrosin structure-based design, synthesis and biological activities of 7-azaindol derivatives as new acrosin inhibitors, Chin. Chem. Lett. 22 (2011) 272-275.
27. [27]
  [27] G.F. Hao, G.F. Yang, C.G. Zhan, Structure-based methods for predicting target mutation-induced drug resistance and rational drug design to overcome the problem, Drug Discov. Today 17 (2012) 1121-1126.
28. [28]
  [28] L. Zhang, Y. Tan, N.X. Wang, et al., Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors, Bioorg. Med. Chem. 18 (2010) 7948-7956.
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沈阳化工大学材料科学与工程学院沈阳 110142