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Design, Synthesis, and Evaluation of X-ray Crystal Structure, Biological Activities, DFT Calculations, and Molecular Docking of Phenyl Imidazolidin-2-One Derivatives

文献类型： 外文期刊

作者： Deng, Xile 1 ; Jin, Can 1 ; Xie, Yong 2 ; Gao, Junbo 3 ; Zhou, Xiaomao 1 ;

作者机构： 1.Hunan Acad Agr Sci, Hunan Agr Biotechnol Res Inst, Hunan Prov Key Lab Biol & Control Weeds, Changsha 410125, Peoples R China

2.Shenyang Sinochem Agrochem R&D Co Ltd, State Key Lab Discovery & Dev Novel Pesticide, Shenyang 110021, Peoples R China

3.Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

关键词： synthesis; crystal structure; imidazolinones; insecticidal activity; fungicidal activity

期刊名称：CRYSTALS （ 影响因子：2.589； 五年影响因子：2.615 ）

ISSN： 2073-4352

年卷期： 2020 年 10 卷 8 期

页码：

收录情况： SCI

摘要： Eight phenyl imidazolinone derivatives were synthesized fromN(2)-(2,4-dimethylphenyl)-N-1-methyformamidine (DPMF) via scaffold-hopping method using the ring-closure approach. The prepared compounds were verified using(1)H and(13)C NMR and HRMS spectroscopies. The structure of compound3cwas confirmed by single-crystal X-ray diffraction analysis. The mean plane of the phenyl and imidazolinone moieties was almost coplanar with an angle of 8.85(4)degrees. In the crystal, molecules were interlinked with intermolecular hydrogen bonds (N-H center dot center dot center dot O and C-H center dot center dot center dot O), generating a network structure. Additionally, compound3fdisplayed the highest insecticidal activity (86.7%) againstPlutella xylostellaat 600 mg/L, which was significantly higher than the insecticidal activity (23.0%) of DPMF. Also, compound3ddisplayed good fungicidal activities againstPhytophthora capsici,Phytophthora sojae, andPhytophthora infestans. Density functional theory (DFT) calculations were performed to explain the insecticidal and fungicidal activities of phenyl imidazolidin-2-one derivatives, especially potent compounds3fand3d. Moreover, the binding modes of compounds3a-hand DPMF against octopamine receptor ofPlutella xylostellawere studied by homology modeling and molecular docking. Therefore, a preliminary structure-activity relationship (SAR) was derived and discussed. These results encourage the exploration of novel insecticides and fungicides based on DPMF.

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