8-氯-6-(三氟甲基)咪唑并[1,2-a]吡啶衍生物的设计合成及其杀线虫和杀菌活性OA
Design,synthesis,and nematicidal and fungicidal activities of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine derivatives
为寻找具有优异活性的新型咪唑并[1,2-a]吡啶类衍生物,本研究以 2-氨基-3-氯-5-三氟甲基为原料,基于活性亚结构拼接策略,设计合成了 2 个系列共 17 个未见文献报道的咪唑并[1,2-a]吡啶类衍生物,其中氨基吡啶类衍生物 12 个(1～12),磺酰肼类衍生物 5 个(13～17),目标化合物结构均通过1 H NMR、13C NMR和HRMS确证,并进行了杀线虫和杀菌活性测定.离体杀线虫活性测定结果显示,目标化合物对秀丽隐杆线虫(Caenorhabditis elegans)和松材线虫(Bursaphelenchus xylophilus)都具有一定的活性,其中化合物 13、15、16 和 17 对秀丽隐杆线虫的 LC50 值分别为 41.04、7.64、36.33 和 34.17 mg/L,优于对照药剂噻唑膦(LC50 值63.69 mg/L).盆栽测定结果显示,化合物 15 和 16 在 50 和 100 mg/L质量浓度下对番茄南方根结线虫(Meloidogyne incognita)的防效分别为 66.11%和 70.00%、58.33%和 66.67%,均略优于对照药剂氟吡菌酰胺(43.33%和 63.33%).离体杀菌活性测定结果显示,化合物 8 对小麦全蚀病菌(Gaeumannomyces graminis)的EC50 值为 2.44 mg/L,显著优于氟吡菌酰胺(144.98 mg/L).整体而言,本研究中含磺酰肼结构的目标化合物显示出一定的杀线虫和杀菌活性,可为 8-氯-6-(三氟甲基)咪唑并[1,2-a]吡啶衍生物的结构修饰提供研究思路.
In order to find new imidazo[1,2-a]pyridine derivatives with excellent activity,using 2-amino-3-chloro-5-(trifluoromethyl)pyridine as the starting material,17 new imidazo[1,2-a]pyridine derivatives,which belong to two series,were designed and synthesized via the active substructure splicing strategy in this study,including 12 aminopyridine derivatives(1-12)and 5 sulfohydrazide derivatives(13-17),followed by the determination of their nematicidal and fungicidal activities.The structures of all the target compounds were confirmed by 1H NMR,13C NMR and HRMS.The in vitro nematicidal activity of target compounds was determined,and the results revealed a certain level of toxicity to Caenorhabditis elegans and Bursaphelenchus xylophilus.The LC50 values of compounds 13,15,16 and 17 against C.elegans were 41.04,7.64,36.33 and 34.17 mg/L,respectively,which were better than that of fosthiazate(63.69 mg/L).The pot assay results for controlling Meloidogyne incognita showed thatthat compounds 15 and 16 achieved control efficacies of 66.11%and 70.00%(at a concentration of 50 mg/L),58.33%and 66.67%(at a concentration of 100 mg/L),respectively.Both compounds outperformed the reference agent fluopyram,which achieved efficacies of 43.33%and 63.33%.The results of in vitro fungicidal activity showed that the EC50 value of compound 8 against Gaeumannomyces graminis was 2.44 mg/L,which was significantly better than that of fluopyram(144.98 mg/L).The target compounds of sulfonyl hydrazide derivatives synthesized in this study showed certain nematicidal and fungicidal activity,which can provide research ideas for the design and modification of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine derivatives.
严越;路炎坤;吴坤;徐志红
长江大学 农学院,湖北 荆州 434025长江大学 农学院,湖北 荆州 434025长江大学 农学院,湖北 荆州 434025长江大学 农学院,湖北 荆州 434025
化学化工
咪唑并[1,2-a]吡啶衍生物氨基吡啶磺酰肼杀线虫活性杀菌活性
imidazo[1,2-a]pyridine derivativesaminopyridinesulfonyl hydrazidesnematicidal activityfungicidal activity
《农药学学报》 2026 (1)
96-105,10
国家自然科学基金(No.31672069,32172400). Supported by the National Natural Foundation of China(No.31672069,32172400).
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