title: Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties.
abstract: A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L-1. Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides.
authors: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. Electronic address: xhliu@zjut.edu.cn.
authors: Xing-Hai
authors: XH
authors: Liu
authors: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China; Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China.
authors: Wen
authors: W
authors: Zhao
authors: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China.
authors: Zhong-Hua
authors: ZH
authors: Shen
authors: Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China.
authors: Jia-Hua
authors: JH
authors: Xing
authors: Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China.
authors: Tian-Ming
authors: TM
authors: Xu
authors: Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China. Electronic address: pengweili@sinochem.com.
authors: Wei-Li
authors: WL
authors: Peng
mesh_terms: D000577:Amides; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D008322:Mammals; D062105:Molecular Docking Simulation; D009348:Nematoda / Q000187:drug effects; D011485:Protein Binding / Q000187:drug effects; D011720:Pyrazoles / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D011950:Receptors, Cholinergic / Q000378:metabolism; D013329:Structure-Activity Relationship; D014431:Tylenchoidea / Q000187:drug effects*
chemical_list: D000577:Amides; D000969:Antinematodal Agents; D011720:Pyrazoles; D011950:Receptors, Cholinergic
keywords: Difluoromethylpyrazole carboxamide; Docking; Flexible chain; Nematicidal activity