N-(2-(3-Chlorophenylamino)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide：合成、晶体结构、分子对接和生物活性,Chemistry & Biodiversity

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N-(2-(3-Chlorophenylamino)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide：合成、晶体结构、分子对接和生物活性
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2019-06-13 , DOI: 10.1002/cbdv.201900118
Aigui Zhang ₁ , Yihua Yang ₁ , Ying Yue ₁ , Ke Tao ₁ , Taiping Hou ₁ , Hong Jin ₁

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继续我们之前关于开发具有潜在抗真菌活性的新型吡唑-4-甲酰胺的研究，化合物 SCU2028，即 N-[2-[(3-氯苯基)氨基]苯基]-3-(二氟甲基)-1-甲基‐1H-吡唑-4-甲酰胺，采用新方法合成，结构特征采用红外光谱、HR-ESI-MS、1H-和 13C-NMR 光谱，并通过单晶 X 射线衍射进一步鉴定。在盆栽试验中，化合物 SCU2028 对立枯丝核菌 (R. solani) 显示出良好的体内抗真菌活性，其 IC50 值为 7.48 mg L-1。在田间试验中，化合物 SCU2028 在 200 gai ha−1 的第一次喷洒后第 7 天的防效为 42.30 %，在第二次喷洒后的第 14 天为 68.10 %，仅略低于 thifluzamide（57.20% 和 71.40 ％，分别）。进一步的体外抑制活性表明，化合物 SCU2028 的抑制能力是联苯吡菌胺的 45 倍，化合物 SCU2028 与 SDH 的分子对接预测了其在靶蛋白 SDH 活性位点的结合方向。这些结果表明，化合物 SCU2028 是防治水稻纹枯病的潜在杀菌剂。

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N‐(2‐(3‐Chlorophenylamino)phenyl)‐3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazole‐4‐carboxamide: Synthesis, crystal structure, molecular docking and biological activities

In continuation of our previous research on the development of novel pyrazole‐4‐carboxamide with potential antifungal activity, compound SCU2028, namely N‐[2‐[(3‐chlorophenyl)amino]phenyl]‐3‐(difluoromethyl)‐1‐methyl‐1H‐pyrazole‐4‐carboxamide, was synthesized by new method, structurally characterized by IR, HR‐ESI‐MS, 1H‐ and 13C‐NMR spectra and further identified by single‐crystal X‐ray diffraction. In pot tests, compound SCU2028 showed good in vivo antifungal activity against Rhizoctonia solani (R. solani) and IC50 value of it was 7.48 mg L−1. In field trials, control efficacy of compound SCU2028 at 200 g.a.i. ha−1 was 42.30 % on the 7th day after the first spraying and 68.10 % on the 14th day after the second spraying, only slightly lower than that of thifluzamide (57.20 % and 71.40 %, respectively). Further in vitro inhibitory activity showed inhibitory ability of compound SCU2028 was 45‐fold higher than that of bixafen and molecular docking of compound SCU2028 to SDH predicted its binding orientation in the active site of the target protein SDH. These results suggested that compound SCU2028 was a potential fungicide for control of rice sheath blight.

更新日期：2019-06-13

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