高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (8): 1375-1382.doi: 10.7503/cjcu20170024

• 有机化学 • 上一篇    下一篇

(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

谭英1, 肖梦武1, 叶姣1, 胡艾希1, 曾子清1, 欧晓明2   

  1. 1. 湖南大学化学化工学院, 长沙 410082;
    2. 湖南化工研究院, 国家农药创制工程技术研究中心, 长沙 410007
  • 收稿日期:2017-01-11 修回日期:2017-06-16 出版日期:2017-08-10 发布日期:2017-06-16
  • 通讯作者: 胡艾希,男,博士,教授,博士生导师,主要从事药物化学研究.E-mail:axhu@hnu.edu.cn;叶姣,女,博士,副教授,主要从事药物化学和制药工艺研究.E-mail:yejiao@hnu.edu.cn E-mail:axhu@hnu.edu.cn;yejiao@hnu.edu.cn
  • 基金资助:

    长沙市科技计划项目(批准号:Kq1602039)资助.

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

TAN Ying1, XIAO Mengwu1, YE Jiao1, HU Aixi1, ZENG Ziqing1, OU Xiaoming2   

  1. 1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;
    2. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, China
  • Received:2017-01-11 Revised:2017-06-16 Online:2017-08-10 Published:2017-06-16
  • Supported by:

    Supported by the Science and Technology Program of Changsha, China(No. Kq1602039).

摘要:

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%.

关键词: 1,3,4-噁二唑, 二乙酸碘苯, 单晶结构, 抑菌活性

Abstract:

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.

Key words: 1,3,4-Oxadiazole, Iodobenzene diacetate, Single-crystal structure, Fungicidal activity

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