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以环己酮和2-硫代乙内酰脲为起始原料,经Knoevenagel缩合反应制得5-亚环己基-2-硫代咪唑啉-4-酮(1),化合物1在乙醇钠/乙醇体系中与碘甲烷反应得到5-亚环己基-2-甲硫基咪唑啉-4-酮(2),化合物2再与相应的取代苯胺或苄胺在冰醋酸体系中回流制得目标化合物5-亚环己基-2-取代氨基咪唑啉酮3a～3r,它们的化学结构经1H NMR,IR,MS和X-ray单晶衍射确证.5-亚环己基-2-对氯苄氨基咪唑啉酮(3q):Mr=335.83,C16H18ClN3O CH4O,Monoclinic,P2(1)/n,ρ=1.264 g/cm3,F(000)=712,Z=4,a=0.59895(12)nm,b=1.2161(2)nm,c=2.4289(5)nm,β=94.03(3)°.初步生物活性测定结果表明:在50μg/mL浓度下,部分目标化合物均对供试菌种显现出一定的抑制活性,其中5-亚环己基-2-对氟苄氨基咪唑啉酮(3p)对油菜菌核的EC50为24.37μg/mL,3q对辣椒疫霉的EC50为28.68μg/mL.
Using cyclohexanone and 2-thiohydantoin as starting materials, 5-cyclohexylidene-2-thioimidazolidin-4-one (1) was obtained by Knoevenagel condensation reaction. 5-cyclohexylidene-2-methylthioimidazol-4-one (2) was obtained by reaction with methyl iodide in ethanol system. Compound 2 was refluxed with the corresponding substituted aniline or benzylamine in glacial acetic acid system to obtain the target compound 5-cyclohexylidene-2-substituted aminoimidazolidinones 3a ~ 3r whose chemical structures were confirmed by1H NMR, IR, MS and X-ray single crystal diffraction.5-cyclohexylidene-2- (3q): Mr = 335.83, C16H18ClN3O CH4O, Monoclinic, P2 (1) /n,ρ=1.264g/cm3, F (000) = 712, Z = 4, a = 0.59895 (12) nm, b = 1.2161 (2) nm, c = 2.4289 (5) nm, β = 94.03 (3) ° .According to the preliminary bioassay results, some of the target compounds showed some inhibitory effects on the tested strains at a concentration of 50μg / mL The EC50 value of 5-cyclohexylidene-2-p-fluorobenzylaminoimidazolidinone (3p) to B. napus was 24.37μg / mL and that of 3q to P. capsici was 28.68μg / mL.