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
收稿日期: 2024-03-14
修回日期: 2024-05-11
网络出版日期: 2024-06-07
基金资助
国家自然科学基金(31672069); 国家自然科学基金(32172400)
Design, Synthesis and Fungicidal and Nematocidal Activity of 1,2,3-Benzotriazine-4-one Oxadiazole Thioether (Sulfone) Methyl Derivatives
Received date: 2024-03-14
Revised date: 2024-05-11
Online published: 2024-06-07
Supported by
National Natural Foundation of China(31672069); National Natural Foundation of China(32172400)
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. 离体抑菌活性测定结果显示, 6-氯-3-(5-乙砜基)-1,3,4-噁二唑-2-基甲基)苯并[d][1,2,3]三嗪-4(3H)-酮(7c)对油菜菌核病菌Sclerotinia scleotiorum具有较好抑制效果, 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, 3-(5-乙硫基)-1,3,4-噁二唑-2-基甲基)苯并[d][1,2,3]三嗪-4(3H)酮(6a)对秀丽隐杆线虫二龄幼虫的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和一定的杀线虫活性, 为新型1,2,3-苯并三嗪-4-酮类衍生物活性研究提供参考.
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, 2024 , 44(11) : 3446 -3455 . DOI: 10.6023/cjoc202403019
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 results of in vitro antibacterial activity assay showed that 6-chloro-3-(5-ethylsulfonyl)-1,3,4-oxadiazo-2-ylmethyl)benzo[d][1,2,3]triazin-4(3H)-one (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). The toxicity of 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 effects of compound 7c against Rhizoctonia solani were 78.51% and 84.48%, and the curative effects of compound 7c were 60.34% and 78.91%, respectively. At low concentrations, the curative effect 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 3-(5-ethylthio)-1,3,4-oxadiazo-2-ylmethyl)benzo[d][1,2,3]triazin-4(3H)one (6a) against 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 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.
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