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Chinese Journal of Organic Chemistry >

0 240713

DOI: https://doi.org/10.6023/oc202403019

ARTICLE

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

  • Zhao Wei ,
  • Li Fengyu ,
  • Zhao Wei ,
  • Zha Run ,
  • Shi Caihua
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  • aCollege of Agriculture, Yangtze University, Jingzhou 434025;
    bInstitute of Advanced Agricultural Science,Hubei University of Arts and Science, Xiangyang 441053

Received date: 2024-03-14

  Revised date: 2024-05-11

  Online published: 2024-07-15

Supported by

National Natural Foundation of China (NO.31672069) and the National Natural Science Foundation of China (NO.32172400)..

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Abstract

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

Cite this article

Zhao Wei , Li Fengyu , Zhao Wei , Zha Run , Shi Caihua . Design, Synthesis and Fungicidal and Nematocidal Activity of 1,2,3 -benzotriazine-4-one Oxadiazole Thioether (sulfone) Methyl Derivatives[J]. Chinese Journal of Organic Chemistry, 0 : 240713 . DOI: 10.6023/oc202403019

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