5-(2-乙基亚环己基)-2-取代氨基咪唑啉酮类化合物的合成及其杀菌活性

Synthesis and fungicidal activity of 5-(2-ethylcyclohexylidene)-2-aminoimidazolin-4-one derivatives

摘要: 以2-乙基环己酮和2-硫代乙内酰脲为起始原料,经Knoevenagel缩合反应制得5-(2-乙基亚环己基)-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-(2-乙基亚环己基)-2-甲硫基咪唑啉-4-酮(2),化合物2再与相应的取代苄胺在冰醋酸体系中回流制得新化合物3a～3f,其化学结构均经1H NMR、IR和MS确证。初步生物活性测定结果表明:在50 μg/mL下,部分目标化合物对油菜菌核病菌Sclerotinia scleotiorum显示出良好的抑制活性,其中3a、3c、3e和3f的EC50值分别为12.10、8.73、10.11和7.67 μg/mL。

Abstract: A series of new 5-(2-ethylcyclohexylidene)-2-aminoimidazolin-4-one derivatives 3a-3f were synthesized via Knoevenagel condensation,methylation and substitution reaction using 2-ethylcyclohexanone and 2-thiohydantoin as starting material.Their structures were confirmed by 1H NMR,IR and MS spectral data.The preliminary bioassay showed that some of the compounds have good fungicidal activity against Sclerotinia scleotiorum at the concentration of 50 μg/mL.The EC50 values of compound 3a,3c,3e and 3f against S.scleotiorum were 12.10,8.73,10.11 and 7.67 μg/mL, respectively.