摘要/Abstract

以三氟苯嘧啶为先导化合物，设计并合成了一系列结构新颖的1，3，4-噻二唑并[3，2-a]嘧啶酮类介离子衍生物.利用¹H NMR，¹³C NMR，¹⁹F NMR和HRMS对其进行结构表征.初步生物活性表明，多数化合物在100 μg/mL浓度下表现出一定的杀虫活性，其中2-（（4-溴苄基）硫基）-8-（（2-氯噻唑-5-基）甲基）-5-氧代-6-（3-（三氟甲基）苯基）-5H-[1，3，4]噻二唑并[3，2-a]嘧啶-8-鎓-7-盐（8b）和2-（（（2-氯噻唑-5-基）甲基）硫基）-8-（（2-氯噻唑-5-基）甲基）-5-氧代-6-（3-（三氟甲基）苯基）-5H-[1，3，4]噻二唑并[3，2-a]嘧啶-8-鎓-7-盐（8d）对白背飞虱（white-backed planthopper，WBPH）的致死率均为70%；此外，部分化合物在浓度为50 μg/mL时对水稻白叶枯病菌（Xanthomonas oryzae pv. oryzae，Xoo），水稻细菌性条斑病菌（Xanthomonas oryzae pv. oryzicola，Xoc）和柑橘溃疡病菌（Xanthomonas citri pv. citri，Xcc）表现出较好的抑抗菌性，其中2-（（2-（三氟甲基）苄基）硫基）-8-（（2-氯噻唑-5-基）甲基）-5-氧代-6-（3-（三氟甲基）苯基）-5H-[1，3，4]噻二唑并[3，2-a]嘧啶-8- 鎓-7-盐（8h）对水稻白叶枯病菌和水稻细菌性条斑病菌的抑制率分别为70.91%和53.34%，均优于对照药剂三氟苯嘧啶（42.85%和51.22%）、噻菌铜（47.76%和23.25%）和叶枯唑（66.97%和17.24%）；2-（（3-（三氟甲基）苄基）硫基）-8-（（2-氯噻唑-5-基）甲基）-5-氧代-6-（3-（三氟甲基）苯基）-5H-[1，3，4]噻二唑并[3，2-a]嘧啶-8-鎓-7-盐（8e）对柑橘溃疡病菌的抑制率为68.97%，优于噻菌铜（35.85%）和叶枯唑（37.53%）.
关键词: 介离子, 1,3,4-噻二唑并[3,2-a]嘧啶酮, 杀虫活性, 抑菌活性
A series of 1,3,4-thiadiazolo[3,2-a]pyrimidinone mesoionic derivatives were designed and synthesized with triflumezopyrim as the leading compound, and their structures were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. The preliminary biological activities indicated that the target compounds showed certain insecticidal activities at 100 μg/mL, of which the lethality rates of 2-((4-chlorobenzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phen-yl)-5H-[1,3,4]-thiadiazolo[3,2-a]pyrimidin-8-ium-7-olate (8b) and 2-(((2-chlorothiazol-5-yl)methyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1,3,4]thiadiazolo-[3,2-a]pyrimidin-8-ium-7-olate (8d) against white-backed planthopper (WBPH) were 70%. Some compounds showed good antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas citri pv. citri (Xcc) at 50 μg/mL, and the inhi-bitory rates of 2-((2-(trifluoromethyl)benzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-8-ium-7-olate (8h) to Xoo and Xoc were 70.91% and 53.34%, respectively, which were better than thiodiazole copper (47.76% and 23.25%) and bismerthiazol (66.97% and 17.24%). The inhibition rate of 2-((3-(tri-fluoromethyl)benzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]-pyrimidin-8-ium-7-olate (8e) to Xcc was 68.97%, which was better than thiediazole copper (35.85%) and bismerthiazol (37.53%)
Key words: mesoionic, 1,3,4-thiadiazolo[3,2-a]pyrimidinone, insecticidal activity, antibacterial activity


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