为了寻找具有生物活性的新化合物,以氟乙酸甲酯、氰乙酰胺和甲酸乙酯为起始原料,经环合、氯化、水解、酰氯化等反应合成了含氟吡啶酰氯中间体,再与醇类和酚类反应合成了一系列含氟吡啶羧酸酯类化合物,总收率约38%.其结构经~1H NMR、~(13)C NMR、IR、MS及元素分析测试技术确证.初步杀虫抑菌活性测试表明,部分化合物1e、1i、1j和1k在500 mg/L浓度下,对淡色库蚊的杀死率在61.9%～100%之间,但对几种受试植物病菌的抑制活性很差.化合物1k活性最好,在500 mg/L时对粘虫(armyworm)和淡色库蚊(culex mosquito)的杀死率均为100%.初步构效关系分析表明,芳杂环酚的该类化合物有较好的活性,而脂肪醇的该类化合物无活性.
In the search of bioactive compounds, a series of fluorine-substituted pyridine-heterocyclic carboxylate compounds were synthesized with methyl fluoroacetate, cyanacetamide, ethyl formic ester, alcoholic and phenolic compounds via ring closure, chlorination, hydrolyzation, acylchloriration and esterification reactions. The overall yield was about 38%. All compounds were characterized by ~1H NMR, ~(13)C NMR, IR, MS and elemental analysis. The preliminary bioassay results show that compounds 1e, 1i, 1j and 1k exhibited 61.9%～100% mortality against culex mosquito at 500 mg/L and little inhibition against several tested fungi. Compound 1k had better bioactivity and exhibited 100% mortality against armyworm and culex mosquito at 500 mg/L. The preliminary structure-activity relationship results reveal that the title phenolic compounds have good bioactivities while the alcoholic compounds do not.
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