2,5-取代-1,3,4-噁二唑衍生物的合成与杀菌活性

Synthesis and Fungicidal Activity of 2,5-Disubstituted-1,3,4-oxadiazole Derivatives

利用生物活性亚结构拼接原理,将吡啶环、噻唑环引入到1,3,4-噁二唑母体结构中,设计并合成了一系列新型含吡啶(噻唑)的1,3,4-噁二唑衍生物.通过IR,1H NMR,EI-MS及元素分析等方法对所合成的化合物进行了结构表征.代表化合物2-(6-氯吡啶-3-甲硫基)-5-(吡啶-4-基)-1,3,4-噁二唑(I)经单晶X衍射证实了结构.初步测定了所合成化合物的杀菌活性,并比较了在1,3,4-噁二唑母体结构中引入噻唑杂环和引入吡啶杂环后其杀菌活性的差异.结果表明:目标化合物对测试的5种菌均具有一定的杀菌活性,对水稻纹枯病的抑制效果普遍优于对其它菌种的抑制效果;在1,3,4-噁二唑母体结构中引入噻唑杂环比引入吡啶杂环对其杀菌活性更有利.

A series of new 2,5-disubstituted-l,3,4-oxadiazole derivatives have been designed and synthesized by adding pyri- dine ring and thiazole ring to the structure of 1,3,4-oxadiazole. The structures of target compounds have been confirmed by 1H NMR, EI-MS, IR spectroscopy and elemental analyses. The structure of 2-[（6-pyridin-3-yl）methylthio]-5-（pyridin-4-yl）- 1,3,4-oxadazole has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess potential fungicidal activities against Fusarium oxyporium, Gibberella zeae, Rhizoctonia solani, Dothiorella gregaria and Colletotrichum gossypii at a dosage of 5.0 × 10-5 g/mL. The fungicidal activities of 1,3,4-oxadiazole derivatives adding thiazole ring were better than those of those adding pyridine ring.