(Z)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮肟(5-芳基-1,3,4-噁二唑-2-基)甲基醚的合成和抑菌活性

以3,3-二甲基-1-(1H-1,2,4-三唑基)-2-丁酮肟为原料,经醚化、肼解及腙化3步反应得到(E)-N'-(取代苯亚甲基)-2-(Z)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)丁基-2-亚甲氨氧基]乙酰肼(3a~3u),化合物3与二乙酸碘苯(IBD)反应,合成了21个(Z)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮肟-(5-芳基-1,3,4-噁二唑-2-基)甲基醚(4a~4u),化合物4的化学结构经核磁共振谱、高分辨质谱和元素分析确证.采用单晶X射线衍射仪测定了化合物4c的晶体结构.抑菌活性测试结果表明,在500 mg/L浓度下,化合物4k,4f,4j和4n对纹枯病菌的防效率分别为70.9%,60.2%,60.0%和60.6%;在25 mg/L浓度下,化合物4b,4c,4d和4e对菌核病菌的抑制率为71.8%~76.9%.

Synthesis,Crystal Structure and Fungicidal Activity of (Z)-3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]oxime

A series of (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-(5-aryl-1,3,4-oxadiazol-2-yl)methyl]oxime(4a-4u) was designed and synthesized via the reaction between iodobenzene diacetate(IBD) and the intermediates, (E)-N′-substituted benzylidene-2-({(Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ylidene]amino}oxy)acetohydrazide(3), which were prepared from (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime via etherification, hydrazinolysis and condensation with various of substituted benzaldehyde.The structures of target compounds 4 were confirmed by muclear magnetian resonance(NMR), high resolution mass spectrum(HRMS) and elemental analysis.The crystal structure of compound 4c was determined by X-ray diffraction analysis.The results of fungicidal activity indicated that some of the title compounds exhibited moderate control rate against Rhizoctonia solani at 500 mg/L and moderate inhibition rate against Sclerotonia sclerotiorum at 25 mg/L.