Studies On Design, Synthesis And Properties Of Novel Imidazolinone Derivatives

Imidazolones, one of the most flourishes in the research and development of agrochemicals, have been found to have widespread biological activities. Some of them have been used as herbicides, fungicides, etc. In order to search for novel imidazolone derivatives which have high activities, according as the connecting principle of actively biological groups, seven series and three kinds of two hundred and twenty-nine unreported imidazolone derivatives were designed and synthesized with good yields. Their structure were characterized by 1H NMR, 13C NMR, GC-MS, LC-MS and IR spectroscopies, and element quantitative analysis. The reaction conditions, the physical and spectral properties, and the biological activities of the newly synthesized imidazolone derivatives were also studied , and many of them were found to show good herbicidal and fungicidal activities. It may be summarized as follows :Two hundred and twelve unreported 3-alkyl-5-aryl(heterocycle)idene-2-thio-imidazoiin-4-one and 3-alkyl-5-aryl(heterocycle)idene-2-alkylsulfanyl-3,5-dihydro-imidazol-4-one in six series weredesigned and synthesized by utilizing Staudinger and aza-Wittig reactions with mild condition andgood yields. Their structure were characterized by *H NMR, 13C NMR, GC-MS, LC-MS and IRspectroscopies, and element quantitative analysis. The cyclization reaction of the primary amines with the intermediate ( IV A- IV C,3-aryl-2-isothiocyanato -acrylic acid ethyl ester) in absence of solid potassium carbonate was studied.The result showed that it was a good method for preparation of compounds (VA - VC, 3-alkyl-5-aryl(heterocycle)idene-2-thio-imidazolin-4-one. The S-alkylation of 3-alkyl-5-aryl(heterocycle)idene-2-thio-imidazolin-4-one (VA-VC) with alkylhalide in presence of dry solid potassium carbonate (K2CO3 : alkyl halide = 1 : 1.2 ~ 6 mol) wasstudied, and the compounds (VIA-VIC, 2-alkylsulfanyl-3-alkyl-5-aryl(heterocycle)idene-3,5-dihydro-imidazol-4-one) were conveniently synthesized at lower temperature . Seventeen unreported 5-alkyI-l-[2-(2,4-dichloro-phenoxy)-acetyl]-3-aryl-imidazolidine-2,4-dione(VID) were designed and synthesized with mild condition and good yields. Their structure werecharacterized by 1H NMR, 13C NMR, GC-MS, LC-MS and IR spectroscopies, and elementalquantitative analysis. The spectral and physical properties of all compounds (VA-VD and VIA-VID) weresystematically studied, respectively.The newly synthesized compounds (VIA-VID) and some intermediates were tested for fungicidal activities against specified microorganisms such as Fusarium oxysporium, Botryosphaeria berengeriana and Rhizoctonia solani, and growth inhibition of Barnyard grass and Cole root and stalk, respectively. The results of bioassay show that some of them exhibit significant biological activities.