Studies On Synthesis And Biological Activity Of Imidazolones And Their Fused Heterocyclic Compounds

Imidazolones have been found to show fungicidal, herbicidal, pesticidal and medicinal activities, and have the applied foreground extensively. In this paper, we have synthesized novel imidazolones by utilizing aza-Wittig reaction, condensation reaction and other cyclizative reactions, which have the advantage of easily accessible starting material, mild condition and good yield. We have studied the spectral properties, biological activities and the good conditions for synthesis. It may be summarized as follows:1. Forty eight unreported imidazolone derivatives in tow series were synthesized. The spectral properties of the products were researched.I : 5-Arylidene-3-benzylimino-2-methylthio-4H-imidazolin-4-onesI -7A~ D. (Forty eight)II: 6-Aryl(heterocyclic)idene-2-bromomethyl-2, 3-dihydrogen-imidazo[2,l-b]thiazol-5 -one II -6A~G.(Seven)2. The condensation of 3- amino-2-methylthio-imidazol-4-ones I -6 with aryl(heterocyclic)aldehyde was carried out in the presence of acetic acid, at between 30DEG and 50DEG, which method was researched deeply. The results show that it is a good method for preparing 5-arylidene-3-benzylimino-2-methylthio-4H-imidazolin-4-ones I -7A~ D.3. The cyclization of 3-allyl-5-arylidene -2-thio-imidazol-4-diones with bromine were researched, by which the 6-aryl(heterocyclic)idene-2-bromomethyl-2, 3-dihydrogen--imidazo[2,l-b]thiazoI-5-one II -6A~G were synthesized. The condition of the reaction and the spectral properties of the products were studied.4. The biological activities of imidazolones derivatives were studied. The results showed that they exhibited herbicidal activity and fungicidal activity. Six of them exhibited 100% inhibition of Cole and Barnyard grass root in 100mg/L. Eighteen of them exhibited 100% inhibition of partial fungi in 50mg/L. The best compounds of I -7Aj(Ar=4-CH3O-C6H4, A1r=2-Thienyl) I -7Bj(Ar=4-CH3-C6H4, Ar1=2-Thienyl), I -7Dg(Ar=4-F-C6H4, Ar1=4-Cl-C6H4) I -7Dh(Ar=4-F-C6H4, Ar1=2-Cl-C6H4), I -7Di(Ar=4-F-C6H4, Ar1=3-Cl-C6H4), I -7Dj(Ar=4-F-C6H4, Ar1=2-Thienyl) exhibited 100% inhibition of Fusarium Osysporum,Gibberella zeae, Cercospora Eticola, Physalospora Piricola, Pellicularia Sasakii in50 mg/L.