5-亚环己基-2-取代氨基咪唑啉酮类化合物的合成及其杀菌活性研究

Synthesis and Fungicidal Activity of 5-Cyclohexylidene-2-aminoimidazolin-4-one Derivatives

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.

A series,of new 5-cyclohexylidene-2-aminoimidazolin-4-one derivatives 3a-3r were synthesized via Knoevena- gel condensation, methylation and substitution reaction using cyclohexanone and 2-thiohydantoin as starting material. Their structures of compounds 3a-3r were confirmed by 1H NMR, IR, MS techniques and X-ray diffraction. 5-Cyclohexylidene- 2-p-chlorobenzylaminoimidazolin-4-one （3q）： Mr= 335.83, C16H18C1N30＊CH40, Monoclinic, P2（1）/n, p= 1.264 g/cm3, F（000）=712, Z=4, a=0.59895（12） nm, b= 1.2161（2） nm, c=2.4289（5） nm, fl=94.03（3）°. The preliminary bioassay shows that some of the compounds have certain fungicidal activities at the concentration of 50 p.g/mL. The ECs0 value of 5-cyclohexytidene-2-p-fluorobenzylaminoimidazolin-4-one （3p） against Sclerotinia scleotiorum is 24.37 μg/mL, and that ot 3q against Phytophthora capsici is 28.68 μg/mL, respectively.