UN PROCEDIMIENTO PARA LA PREPARACION DE NUEVOS DERIVADOS DE URAZOL 1,2,4-SUSTITUIDOS.

摘要

1497189 Substituted phenyl urazoles MITSUBISHI CHEMICAL INDUSTRIES Ltd 8 Dec 1975 [6 Dec 1974 13 Dec 1974] 50277/75 Heading C2C The invention comprises compounds of the formula wherein X and Y are each O or S, R 1 and R 2 are H, alkyl, alkenyl, alkynyl, aryl which may be substituted by halogen or alkyl; alkanoyl, alkylcarbamoyl, alkoxycarbonyl, alkylthiocarbamoyl or (alkylthio)thiocarbonyl (provided that R 1 and R 2 are not both H when X and Y are both oxygen) or R 1 and R 2 together form a (C 3 -C 8 ) alkylene radical which may have CH 3 substituents as branches. They may be obtained by (a) reacting an alkali metal, alkaline earth metal or NH 4 salt of 4-(31,51-dichlorophenyl) urazole with a halide of formula RHal wherein R is R1 or R2 to give either a product in which R1 and R2 are the same, or a product in which R1 is R and R2 is H and, if required, further reacting with a different halide of formula RHal to give a product in which R1 and R2 are different; (b) reacting 4-(31,51-dichlorophenyl) urazole in one or more stages with an isocyanate or isothiocyanate of the formula R4NCX wherein R4 is alkyl and X is O or S; (c) when one or both of X and Y is S, reacting a compound of Formula I in which X and Y are both O with P 2 S 5 ; (d) reacting a 1,2-disubstituted-1-alkoxycarbonyl hydrazine of the formula wherein R 5 is lower alkyl, with 3,5-dichlorophenyl isocyanate or isothiocyanate, and cyclizing the resulting carbamoyl- or thiocarbamoyl - hydrazine by treating the carbamoyl-hydrazine with KOH or NaOC 2 H 5 and heating the thiocarbamoyl-hydrazine; (e) Diels-Alder condensation of 4-(31,51-dichlorophenyl)urazole with a diene of the formula wherein R6, R7, R8 and R9 are each H or CH 3 , to give a compound of the formula and then hydrogenating this compound to give a compound of the formula or (f) when R 1 and R 2 together form a (C 3 -C a ) alkylene radical which may have CH 3 substituents, reacting a monovalent or bivalent metal salt of amine salt of 4-(31,51-dichlorophenyl)urazole with an alkylene dihalide. A fungicidal composition comprises a compound of Formula I above together with a carrier or diluent. It is useful in preventing rice sheath blight disease, Botrysis gray mould disease, rice brown spot disease, Altemaria leaf spot and Sclerotinia spot disease.