新型先导化合物4-[4-(3,4-二甲氧苯基)-2-甲基噻唑-5-甲酰基]吗啉的设计、合成与生物活性

Design, Synthesis, and Biological Activity of a Novel Lead Compound4-[4-(3,4-Dimethoxyphenyl)-2-methylthiazole-5-carbonyl ] morphol ine

以3,4-二甲氧基苯乙酮为原料,经酯化、氯化、环化、水解、酰氯化和胺化六步制得新型先导化合物4-[4-(3,4-二甲氧苯基)-2-甲基噻唑-5-甲酰基]吗啉(5)。化合物5及其中间体的化学结构经红外、核磁、高分辨质谱和元素分析确认。生物活性测定结果表明化合物5在300g a.i.／hm2剂量下对马铃薯晚疫病的防效为90％。

A novel lead compound, 4-[4-(3, 4-dimethoxyphenyl)-2-methyl-thiazole-5-carbonyl] morpholine (5), was designed and synthesized from 3, 4-dimethoxyacetophenone via six steps: esterification, chlormation, ring condensation, and hydrolysis to form the free acid, followed by formation of the acid chloride which, when reacted with morpholine, produces the desired amide (5). The chemical structures of 5 and its precursors were confirmed by IR, 1H NMR, HRMS, and elemental analysis. Biological activity testing in the greenhouse indicated that compound 5 has good fungicidal activity, with 300 g a.i./ha providing 90% control of tomato late blight.