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

doi:10.6023/oc202403019

研究论文

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,*

^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 Wei^a, Li Fengyu^a, Zhao Wei^a, Zha Run^a, Shi Caihua^b,

^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)..

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摘要/Abstract

为了寻找高活性的新化合物, 设计并合成了20个含噁二唑片段的1,2,3-苯并三嗪-4-酮硫醚(砜)类衍生物. 通过¹H NMR、¹³C NMR和高分辨质谱（HRMS）确证了化合物的结构. 离体抑菌活性测定结果显示: 化合物7c对油菜菌核病菌Sclerotinia scleotiorum具有较好抑制效果, 其EC₅₀值为3.84 mg/L, 与对照药剂噁霉灵(5.43 mg/L)相当; 7c (1.81 mg/L)对水稻纹枯病菌Rhizoctonia solani的毒力与对照药剂多菌灵(1.09 mg/L)相当, 显著高于对照药剂噁霉灵(45.70 mg/L). 在100和200 mg/L浓度下, 化合物7c对水稻纹枯病菌保护防效分别为78.51%和84.48%, 治疗防效分别为60.34%和78.91%, 低浓度时的治疗防效与多菌灵(61.53%)相当. 离体杀线虫活性测定结果显示: 浓度为100 mg/L时, 部分化合物对秀丽隐杆线虫和松材线虫有一定的活性, 化合物6a对秀丽隐杆线虫二龄幼虫LC₅₀值为3.96 mg/L, 优于对照药剂噻唑磷(57.39 mg/L), 与氟吡菌酰胺(4.68 mg/L)相当; 化合物6a(50.28 mg/L)对松材线虫的毒力低于噻唑磷(24.68 mg/L)和氟吡菌酰胺(0.57 mg/L). 本研究所合成的目标化合物具有较高杀菌活性与一定的杀线虫活性, 可为新型1,2,3-苯并三嗪-4-酮类衍生物活性研究提供参考.

关键词: 1,2,3-苯并三嗪-4-酮, 噁二唑, 硫醚, 砜, 抑菌活性, 杀线虫活性

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 by¹H 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

引用此文

赵薇, 李凤宇, 赵伟, 查润, 史彩华, 徐志红. 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[J]. 有机化学, doi: 10.6023/oc202403019.

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, doi: 10.6023/oc202403019.

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