Synthesis, Crystal Structure, and Fungicidal Activity of Novel 1,5-Diaryl-1H-pyrazol-3-oxyacetate Derivatives

A series of ethyl 2-(1,5-diaryl-1H-pyrazol-3-yloxy)acetate derivatives (5a-5i) have been efficiently synthesized by the reaction of 1,5-diaryl-1H-pyrazol-3-ols (4a-4i) with ethyl 2-bromoacetate. The structures of the newly synthesized compounds were characterized by (1)H NMR spectra and elemental analysis, and the crystal structure of the compound ethyl 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)acetate (5c) was determined by single crystal X-ray diffraction analysis. The compound 5c belongs to triclinic system with space group P(-1), a = 5.8170(12) angstrom, b = 11.804(2) angstrom, c = 12.783(2) angstrom, alpha = 83.89(2)degrees, beta = 89.24(3)degrees, gamma = 89.73(3)degrees, Formula weight: 356.80, Triclinic V = 872.7(3) angstrom(3), D(c) = 1.358 mg/m(3), Z = 2, F (000) = 372. Bioassay results indicated that the compound ethyl 2-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)acetate (5d) exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 mu g/mL.