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Molecules 2015, 20(5), 8395-8408; doi:10.3390/molecules20058395

Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides

1
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
2
College of Agricultural and Forestry Science and Technology, Hebei North University, Zhangjiakou 075131, Hebei, China
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 7 April 2015 / Revised: 24 April 2015 / Accepted: 5 May 2015 / Published: 8 May 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [937 KB, uploaded 8 May 2015]   |  

Abstract

A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH. View Full-Text
Keywords: fungicidal activity; SDHIs; CoMFA; molecular docking fungicidal activity; SDHIs; CoMFA; molecular docking
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Du, S.; Tian, Z.; Yang, D.; Li, X.; Li, H.; Jia, C.; Che, C.; Wang, M.; Qin, Z. Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides. Molecules 2015, 20, 8395-8408.

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