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1,2,3-苯并三嗪-4-酮噁二唑硫醚(砜)甲基衍生物的设计、合成及杀菌和杀线虫活性

赵薇a, 李凤宇a, 赵伟a, 查润a, 史彩华b, 徐志红a,*   

  1. a长江大学农学院 荆州 434025;
    b湖北文理学院现代农业研究院 襄阳 441053
  • 收稿日期:2024-03-14 修回日期:2024-05-11
  • 基金资助:
    国家自然科学基金(NO.31672069)、国家自然科学基金(NO.32172400)资助项目.

Design, Synthesis and Fungicidal and Nematocidal Activity of 1,2,3 -benzotriazine-4-one Oxadiazole Thioether (sulfone) Methyl Derivatives

Zhao Weia, Li Fengyua, Zhao Weia, Zha Runa, Shi Caihuab,   

  1. aCollege of Agriculture, Yangtze University, Jingzhou 434025;
    bInstitute of Advanced Agricultural Science,Hubei University of Arts and Science, Xiangyang 441053
  • Received:2024-03-14 Revised:2024-05-11
  • Contact: * E-mail: x_u_78@sina.com
  • Supported by:
    National Natural Foundation of China (NO.31672069) and the National Natural Science Foundation of China (NO.32172400)..

In order to find new compounds with high activity, 20 1,2,3-Benzotriazin-4-one thioether (sulfone) derivatives containing oxadiazole fragments were designed and synthesized. The structure of the compounds was confirmed by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). Compound 7c had a good inhibitory effect on Sclerotinia sclerotiorum, with an EC50 value of 3.84 mg/L, which was comparable to that of the control agent hymexazol (5.43 mg/L); 7c (1.81 mg/L) against Rhizoctonia solani was comparable to that of carbendazim (1.09 mg/L), and significantly higher than that of the control agent hymexazol (45.70 mg/L). At the concentrations of 100 and 200 mg/L, the protective and curative effects of compound 7c against Rhizoctonia solani was 78.51% and 84.48%, and the curative effects was 60.34% and 78.91%, respectively, At low concentrations, the curative effects was comparable to that of carbendazim (61.53%). At a concentration of 100 mg/L, some compounds had certain in vitro activities against Caenorhabditis elegans and Bursaphelenchus xylophilus, and the LC50 value of compound 6a against the J2 of C. elegans was 3.96 mg/L, which was better than that of Fosthiazate (57.39 mg/L) and comparable to that of fluopyram (4.68 mg/L). However, the virulence of compound 6a (50.28 mg/L) against B. xylophilus was lower than that of fosthiazate(24.68 mg/L) and fluopyram (0.57 mg/L). The target compounds synthesized in this study have high fungicidal activity and certain nematicidal activity, which can provide a reference for the study of new 1,2,3- benzotriazine-4-one derivatives.

Key words: 1,2,3-Benzotriazin-4-one, oxadiazole, thioether, sulfone, fungicidal activity, nematocidal activity