Synthesis, Crystal Structure, and Fungicidal activity of Novel 1-Aryl-3-Oxypyrazoles Containing a Z -Configuration Methyl 2-(Methoxyimino) Acetate Moiety

Six novel methyl(Z)-2-(4-{[(1-aryl-1H-pyrazol-3-yl)oxy]methyl}phenyl) 2-(methoxyimino)acetate were synthesised by the reaction of 1-aryl-1H-pyrazol-3-ols with methyl (Z)-2-[4-(bromomethyl)phenyl]-2-(methoxyimino)acetate. The structure of methyl (Z)-2-[4-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}meth...

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Published in:Journal of chemical research 2014-09, Vol.38 (9), p.520-523
Main Authors: Liu, Yuanyuan, Li, Yi, Chen, Nanqing, Xiong, Xiaohui, Yu, Lu, Jing, Chaoxuan, Zheng, Qiang, Du, Kang, Jiang, Huiying
Format: Article
Language:English
Subjects:
Acetates
Bioassay
Crystal structure
Derivatives
Diffraction
Fungicides
Rhizoctonia solani
Synthesis
X-rays
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Summary:Six novel methyl(Z)-2-(4-{[(1-aryl-1H-pyrazol-3-yl)oxy]methyl}phenyl) 2-(methoxyimino)acetate were synthesised by the reaction of 1-aryl-1H-pyrazol-3-ols with methyl (Z)-2-[4-(bromomethyl)phenyl]-2-(methoxyimino)acetate. The structure of methyl (Z)-2-[4-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]- 2 -(methoxyimino)acetate was also determined by single-crystal X-ray diffraction analysis. A preliminary in vitro bioassay indicated that compounds 3-chlorophenyl, 4-chlorophenyl and 4-fluoro-3-(trifluoromethyl) derivatives exhibited moderate fungicidal activity against Rhizoctonia solani at a dosage of 10 mu g mL-1.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751914X14068939771826