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

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.

Graphical abstractA series of N-fluorine-containing phenyl-N′-pyrimidylurea derivatives were synthesized. Compound 25 (N-(3-trifluoromethylphenyl)-N′-(2-amino-4-chloro-6-methylpyrimidyl) urea) exhibited marked herbicidal activity against Setaria viridis (SV) (IC50 = 11.67 mg/L) and was more potent than bensulfuron (IC50 = 27.45 mg/L), a commercially available herbicide. A statistically significant CoMFA model with high predict abilities (q2 = 0.869, r2 = 0.989) were obtained.Figure optionsDownload full-size imageDownload as PowerPoint slide