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有机化学
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有机化学 ›› 2021, Vol. 41 ›› Issue (2): 826-832.DOI: 10.6023/cjoc202006037 上一篇    下一篇

研究简报

新型含三唑的烯丙基苯甲酸酯类化合物的合成及杀菌活性研究

余玮a, 王翰a, 闵莉静b, 华学文c, 刘幸海a,*()   

  1. a 浙江工业大学化学工程学院 杭州 310014
    b 湖州师范学院生命科学院 浙江湖州 313000
    c 聊城大学农学院 山东聊城 252000
  • 收稿日期:2020-06-19 修回日期:2020-07-20 发布日期:2020-10-22
  • 通讯作者: 刘幸海
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    浙江省自然科学基金(LY19C140002); 浙江省教育厅(Y201941832)

Synthesis and Fungicidal Activity of Novel Allyl Benzoate Compounds Containing Triazole

Wei Yua, Han Wanga, Li-Jing Minb, Xue-Wen Huac, Xing-Hai Liua,*()   

  1. a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
    b Key Laboratory of Vector Biology and Pathogen Control of Zhejiang Province, College of Life Science, Huzhou University, Huzhou, Zhejiang 313000
    c College of Agriculture, Liaocheng University, Liaocheng, Shandong 252000
  • Received:2020-06-19 Revised:2020-07-20 Published:2020-10-22
  • Contact: Xing-Hai Liu
  • Supported by:
    the Natural Science Foundation of Zhejiang Province(LY19C140002); the Research Fund of Department of Education of Zhejiang Province(Y201941832)

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为了寻找高杀菌活性的农药先导化合物, 设计合成了一系列未见文献报道的含三唑的烯丙基苯甲酸酯类化合物, 其结构经1H NMR和HRMS进行了确证, 用X射线单晶衍射测定了(R,S)-(Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基2,3-二氯苯甲酸酯(5j)的晶体结构. 生物活性测定结果表明, 在50 mg/L的浓度下, (R,S)-(Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基苯甲酸酯(5a), (R,S)-(Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基2-氟苯甲酸酯(5g)和(R,S)-(Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基3-甲基苯甲酸酯(5n)对油菜菌核的抑菌率均达到了70%以上, 显示出了较高的杀菌活性.

关键词: 关键词 三唑类杀菌剂, 合成, 杀菌活性, 构效关系(SAR)

In order to find pesticide lead compounds with high fungicidal activity, a series of unreported allyl benzoate compounds containing triazole were designed and synthesized. The structures were confirmed by 1H NMR and HRMS, and the crystal structure of (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl 2,3-dichlorobenzoate (5j) was determined by X-ray single crystal diffraction. The bioassay results showed that (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl benzoate (5a), (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allyl 2-fluorobenzoate (5g) and (R,S)-(Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1- yl)allyl 3-methylbenzoate (5n) exhibited good control efficacy against Sclerotinia sclerotiorummore than 70% at 50 mg/L.

Key words: triazole fungicide, synthesis, fungicidal activity, structure activity relationship (SAR)