Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 397-405.DOI: 10.6023/cjoc201807009 Previous Articles     Next Articles

ARTICLE

苯基吡唑氧基丙酸衍生物的设计、合成及其对水稻纹枯病的杀菌活性

于福强a,b, 关爱莹b, 孙旭峰b, 李慧超b, 李小武a   

  1. a 东北大学材料科学与工程学院 材料物理与化学系 材料各向异性与织构教育部重点实验室 沈阳 110819;
    b 沈阳中化农药化工研发有限公司 新农药创制与开发国家重点实验室 沈阳 110021
  • 收稿日期:2018-07-04 修回日期:2018-09-05 出版日期:2019-02-25 发布日期:2018-10-12
  • 通讯作者: 关爱莹, 李小武 E-mail:guanaiying@sinochem.com;xwli@mail.neu.edu.cn
  • 基金资助:

    辽宁省科技计划基金(No.2015306001)资助项目.

Design, Synthesis and Fungicidal Activity against Rhizoctonia solani of New Phenylpyrazoloxyl Propionic Acid Derivatives

Yu Fuqianga,b, Guan Aiyingb, Sun Xufengb, Li Huichaob, Li Xiaowua   

  1. a Key Laboratory for Anisotropy and Texture of Materials, Ministry of Education, Department of Materials Physics and Chemistry, School of Material Science and Engineering, Northeastern University, Shenyang 110819;
    b State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R & D. Co. Ltd., Tiexi District, Shenyang 110021
  • Received:2018-07-04 Revised:2018-09-05 Online:2019-02-25 Published:2018-10-12
  • Contact: 10.6023/cjoc201807009 E-mail:guanaiying@sinochem.com;xwli@mail.neu.edu.cn
  • Supported by:

    Project supported by the Liaoning Provincal Science and Technology Plan Projects (No. 2015306001).

Rice sheath blight disease, one of three most important diseases in rice, can lead to crop production loss seriously. However, the application of fungicides is an effective way to prevent rice from diseases. After being used for a period of time, the plant pathogenic fungi may develop resistance to chemical fungicide, so it is necessary to discover compounds with novel structures and further to address the problem of fungicide resistance. By employing the intermediate derivatisation method (IDM), twenty-five new phenylpyrazoloxyl propionic acid derivatives were designed and synthesized. The biological activities of title compounds were tested against Rhizoctonia solani and their structure-activity relationships (SAR) were discussed as well. The preliminary bioassay results displayed that some compounds exhibited an excellent fungicidal activity against Rhizoctonia solani, especially 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)-N-(4-nitrophenyl)propanamide (17) (EC50=1.05 mg/L) and 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)-N-(pyridin-2-yl)propanamide (22) (EC50=1.02 mg/L) showing a com-parable activity to the commercial contrast tebuconazole (EC50=1.02 mg/L), and 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy)-N-(3,4-dichlorophenyl)propanamide (20) (EC50=0.95 mg/L) is a little more active than tebuconazole (EC50=1.02 mg/L).

Key words: phenylpyrazoloxyl propionic acid derivatives, intermediate derivatization method, fungicidal activity, Rhizoctonia solani, structure-activity relationship