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Synthesis, crystal structure, and fungicidal activity of novel 1,5-diaryl-1H-pyrazol-3-oxyacetate derivatives

✍ Scribed by Yuanyuan Liu; Hong Shi; Yufeng Li; Hongjun Zhu


Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
398 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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A series of ethyl 2‐(1,5‐diaryl‐1__H__‐pyrazol‐3‐yloxy)acetate derivatives (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i) have been efficiently synthesized by the reaction of 1,5‐diaryl‐1__H__‐pyrazol‐3‐ols (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 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‐1__H__‐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) Å, b = 11.804(2) Å, c = 12.783(2) Å, α = 83.89(2)°, β = 89.24(3)°, γ = 89.73(3)°, Formula weight: 356.80, Triclinic V = 872.7(3) Å^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‐1__H__‐pyrazol‐3‐yloxy)acetate (5d**)** exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 μg/mL. J. Heterocyclic Chem., (2010).


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