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有机化学 ›› 2010, Vol. 30 ›› Issue (06): 923-927. 上一篇    下一篇

研究简报

4-叔丁基-5-（1,2,4-三唑-1-基）-2-苄亚氨基噻唑的合成、晶体结构和生物活性

胡艾希1,覃智2,陈平3,叶姣4   

  1. 1. 湖南大学化学化工学院
    2.
    3. 浙江大学化学系
    4. 湖南大学 化学化工学院
  • 收稿日期:2009-10-20 修回日期:2010-01-11 发布日期:2010-06-30
  • 通讯作者: 胡艾希 E-mail:axhu@hnu.cn
  • 基金资助:
    国家级.863计划

Synthesis, Characterization and Biological Activity of (E)-N-Benzylidene-4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amines

, , ,   

  • Received:2009-10-20 Revised:2010-01-11 Published:2010-06-30

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以氯代片那酮为原料，经1,2,4-三唑取代，溴代，硫脲环合得到4-叔丁基-5-（1,2,4-三唑-1-基）-2-氨基噻唑；再与芳醛缩合合成一系列新4-叔丁基-5-（1,2,4-三唑-1-基）-2-苄亚氨基噻唑（5）。用单晶 X-射线衍射测定了化合物5i 的晶体结构。化合物5i 的晶体属三斜晶系, 空间群为P-1, 晶胞参数为: a = 0.79748(4) nm, b = 1.01803(5) nm, c = 1.14603(6) nm, α = 102.882(1)°, β = 100.253(1) °, γ = 1104.457(1)°; V = 0.850.95(7) nm3, Z = 2, Dc = 1.484 g/ cm3, F (000) = 392, R1 = 0.030, wR2 = 0.100, S = 1.10。生物活性实验结果表明：化合物5c（25 mg/L）对小麦赤霉病菌、稻曲病菌、对黄瓜灰霉病菌和稻纹枯病菌的抑制率分别为分别为100%、100%、82.8%和80.3%。化合物5d（25 mg/L）对稻纹枯病菌、油菜菌核病菌、小麦赤霉病菌和稻曲病菌的抑制率分别为100%、95.5%、100%和100%。化合物5e（25 mg/L）对小麦赤霉病菌的抑制率为100%。5d对小麦赤霉病菌、油菜菌核病菌和水稻纹枯病菌的EC50值分别为1.16mg/L 、1.38 mg/L 和1.47 mg/L。

关键词: 氨基噻唑, 合成, 杀菌活性, 晶体结构

A novel series of (E)-N-benzylidene-4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amines have been designed and synthesized by reaction 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine and substituted aromatic aldehydes. Their structures were clearly established by MS, 1H NMR spectra. The crystal structure of compound 5i has been determined by X-ray diffraction analysis. The compound 5i crystal belongs to Triclinic system with space group P-1 and cell parameters: a = 0.79748(4) nm, b = 1.01803(5) nm, c = 1.14603(6) nm, α = 102.882(1)°, β = 100.253(1) °, γ = 1104.457(1)°; V = 0.850.95(7) nm3, Z = 2, Dc = 1.484 g/ cm3, F (000) = 392, R1 = 0.030, wR2 = 0.100, S = 1.10．The preliminary bioassays indicated that compound 5c exhibited 100 %, 100 % , 82.8% and 80.3% inhibition rate against G. zeae, U. virens, B. cinerea and R. solani at 25 mg/L. The compound 5d exhibited 100%, 95.5%, 100% and 100% inhibition rate against R. solani, S. scerotirum, G. zeae and U. virens) at 25 mg/L. The compound 5e exhibited 100 % inhibition rate against G. zeae . EC50 values of 5d were 1.16 mg/L, 1.38 mg/L and 1.47 mg/L against G. zeae, S. scerotirum and R. solani respectively.