title: Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides.
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.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. dsj5216@163.com.
authors.forename: Shijie
authors.initials: S
authors.lastname: Du
authors.affiliation: College of Agricultural and Forestry Science and Technology, Hebei North University, Zhangjiakou 075131, Hebei, China. nkxtzm@163.com.
authors.forename: Zaimin
authors.initials: Z
authors.lastname: Tian
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. yangdy@cau.edu.cn.
authors.forename: Dongyan
authors.initials: D
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. lixiuyun0115@163.com.
authors.forename: Xiuyun
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. lihong129106@163.com.
authors.forename: Hong
authors.initials: H
authors.lastname: Li
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. cauchangqing@gmail.com.
authors.forename: Changqing
authors.initials: C
authors.lastname: Jia
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. chechuanliang@cau.edu.cn.
authors.forename: Chuanliang
authors.initials: C
authors.lastname: Che
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. woookooo@cau.edu.cn.
authors.forename: Mian
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. qinzhaohai@263.net.
authors.forename: Zhaohai
authors.initials: Z
authors.lastname: Qin
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000494:pharmacology; D002227:Carbazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development*; D009536:Niacinamide / Q000031:analogs & derivatives / Q000494:pharmacology; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000577:Amides; D000935:Antifungal Agents; D001713:Biphenyl Compounds; D002227:Carbazoles; D009536:Niacinamide; C550088:2-chloro-N-(4-chlorobiphenyl-2-yl)nicotinamide
keywords: CoMFA; SDHIs; fungicidal activity; molecular docking