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Synthesis, Bioactivities and Structure Activity Relationship of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N '-phenyl Ureas

文献类型： 外文期刊

作者： Guo Dandan 1 ; Wang Zhiwen 1 ; Fan Zhijin 1 ; Zhao Hui 1 ; Zhang Wei 2 ; Cheng Jiagao 2 ; Yang Jiaqiang 3 ; Wu Qingjun 3 ; Z 1 ;

作者机构： 1.Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

2.E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

3.Chinese Acad Agr Sci, Inst Vegetables & Flowers, Beijing 100081, Peoples R China; Sichuan Funct Heterocycl Cpds Engn Technol Res Ct, Mianyang 621000, Sichuan, Peoples R China

4.Chinese Acad Agr Sci, Inst Vegetables & Flowers, Beijing 100081, Peoples R China; Sichuan Funct Heterocycl Cpds Engn Technol Res Ct, Mianyang 621000,

关键词： 4-methyl-1;2;3-thiadiazole derivatives;benzoylurea pesticides;insecticidal activity;3D QSAR model

期刊名称：CHINESE JOURNAL OF CHEMISTRY （ 影响因子：6.0； 五年影响因子：3.19 ）

ISSN： 1001-604X

年卷期： 2012 年 30 卷 10 期

页码：

收录情况： SCI

摘要： Twenty nine novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N'-phenyl ureas were designed and synthesized, and their structures were confirmed by proton nuclear magnetic resonance (1H NMR), infra red spectroscopy (IR) and high-resolution mass spectroscopy (HRMS). Compounds V-9, V-11, V-12, V-15, V-19, V-21, V-22 and V-24 exhibit excellent activity against Culex pipiens pallens. Compounds V-12 and V-22 present good insecticidal activity against Plutella xylostella L. Their median lethal concentrations (LC50) are 164.15 and 89.69 mg center dot L-1, respectively. Compound V-11 also has potential wide spectrum of fungicide activity. Its median effective concentrations (EC50) detected from 3.82 mu g center dot mL-1 against Physalospora piricola to 31.60 mu g center dot mL-1 against Cercospora arachidicola. Compounds V-15 and V-24 show outstanding induction activities as same as positive controls TDL and ningnanmycin, furthermore V-24 has the highest induction activity of 41.85%+/- 4.43%. To elucidate the structure activity relationship in these compounds, a 3D-QSAR model has been built. The established model showed a reliable predicting ability with q2 values of 0.643 and r2 values of 0.982.

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