Synthesis And Property Of Imidazolones And Triazoloquinazolinones

Many azole compounds have been found to show widespread biological activities. Some of them have been used as fungicide, herbicide, pesticide and medicine .In this paper, we studied the synthesis of novel imidazolones and triazoloquinazolinones by utilizing aza-Wittig reaction. The spectral properties and biological activities of some compounds were also researched and some of them were found to show good fungicidal activities. More than sixty unreported compounds in two parts were synthesized, it may be summarized as follows:1. Anew synthetic method to 2-dialkylthio-5-arylmethylene- 3-phenylamino-4H-imidazolin- 4-ones was proposed. This synthetic method has the advantage of easily accessible starting material, mild condition and good yields.2. The reaction of isothiocyanates with phenylhydrazine was researched. The results showed that it can generate thioureas or 2-thioxo-4-imidazolin-4(3H)-ones via the intermediates of thioureas.3. A new synthetic approach was used to prepare 2-phenylamino-3-amino -quinazolin-4(3H)-one, from which novel functionalized iminophosphoranes 15 was synthesized. At the same time, the reaction about iminophosphorane 15 was also studied.A: Iminophosphorane 15 reacted with acyl chloride to generate 2-alkyl(aryl)-l,2,4-triazolo[5,l-b]quinazolin-9(3H)-onesB: Iminophosphorane 15 reacted with aromatic isocyanates to generate 2-arylamino-1,2,4-triazolo[5,1 -b]quinazolin-9(3H)-onesC: Iminophosphorane 15 reacted with CS2 or CO2 to generate 2-thioxo-1,2,4-triazolo[5,1-b]quinazolin-9(3H)-ones or 1,3-dihydro-1,2,4-triazolo [5,1-b]quinazolin-2,9-dione, S-Alkylation of l,3-dihydro-2-thioxo-l,2,4-triazolo [5,1-b]quinazolin-9(3H)-ones with alkylhalide in the presence of solid potassium carbonate gave 2-alkylthio-l,2,4-triazolo[5,l-b]quinazolin-9(3/f)-ones insatisfactory yields.4. The biological activities of partial compounds were studied. The results showed that some of compounds exhibit obviously fungicidal activity. In all these compounds, imidazolones compounds 41' exhibited 91% inhibition of Botrytis Cinerea pers in 50mg/L; and l,2,4-triazolo[5,l-b]qumazolin-9(3//)-ones 23c exhibited 100% inhibition of Pyricularia oryzae, Botrytis Cinerea Pers, Cercospora beticola Sacc in 50mg/L.