Study On The Synthetic Of New Imidazolinone Compounds And Fungicidal Activity

Recently many N-heterocycles are used as fungicides owning to their good activity against most fungi or bacterium. This has resulted in very active study in preparing novel heterocycles to discover new drugs or agricultural chemicals. Among them azole compounds have been fully researched due to their high fungicidal activities. Since Bayer and Janssen company firstly reported the fungicidal activities of 1-substituted triazoles,many triazole-type fungicides have been discovered such as Triadimefon,Triadimenol,Fluotrimazole,Biloxazol, Propiconazole. Until now many other triazoles have been synthesized, however, some synthetic methods are not satisfied due to low yields or harsh conditions. The tandem three component aza-Wittig reaction has the advantages of mild condition and high yields. By successful utility of this method,we report here the synthesis of thirty-one unreported azole compounds as follows: A: 2-(lH-l,2,4-triazol-l-yl)-4H-imidazolin-4-ones (13 compounds)The condition for synthesis of (A) are very important factors influencing the yields and purity of the product. In preparing (A),the catalyst K2CO3(s) must be excess and the reaction time must be 12-13 min.,otherwise a dark solution will be resulted which lead to low yield. By using tandem aza-Wittig reaction,triazolyl and quinolinoxy group were introduced into the molecule of imidazolinones in order to improve their fungicidal activities. This method has the advantages of mild condition and high yields. Thirty-one unreported compounds were synthesized and their fungicidal activities were tested. The results show that some of them exhibited good fungicidal activities.