Patent ID: 6455697
Filing Date: 2002-09-24
Classification: A01N,C07D

Abstract:
A process for preparing substituted phenyluracils of the general formula (I) in whichR1 represents hydrogen, halogen or optionally substituted alkyl, R2 represents optionally substituted alkyl, R3 represents hydrogen, amino or respectively optionally substituted alkyl, alkenyl or alkinyl, R4 represents hydrogen, cyano or halogen, R5 represents cyano or thiocarbamoyl, and R6 represents one of the groupings below â€”C(R7,R8)â€”C(R7,R8)â€”R9 or â€”C(R7)&boxH;C(R8)â€”R9 â€ƒin which R7 and R8 are identical or different and each represents independently of the other hydrogen, hydroxyl, mercapto, halogen or respectively optionally substituted alkyl, alkoxy or alkylthio, and R9 represents cyano, formyl, alkylcarbonyl, the grouping â€”COâ€”OR10 or the grouping â€”COâ€”N(R11,R12), where R10 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl and heterocyclylalkyl, R11 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkoxy, alkenyl and alkinyl, and R12 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl and heterocyclylalkyl, or together with R11 represents alkanediyl characterized in that (a) aminophenyluracils of the general formula (II) in which R1, R2, R3, R4, and R5 are each as defined above, or acid adducts of compounds of the formula (II) are reacted with an alkali metal nitrite or alkyl nitrite and with a hydrogen halide (HX1) or a metal halide (MX1), if appropriate in the presence of a diluent and the resulting diazonium salts of the general formula (III) â€ƒin which R1, R2, R3, R4 and R5 are each as defined above and X1 represents halogen, are reacted with acrylic acid derivatives of the general formula (IV) C(R7,R8)&boxH;C(R7)â€”R9â€ƒâ€ƒ(IV) in which R7, R8, and R9 are each as defined above, in the presence of hydrogen halides (HX1), if appropriate in the presence of catalysts, if appropriate in the presence of water and if appropriate in the presence of the organic solvent employed initially, or (b) substituted phenyluracils of the general formula (Ia) in which R1 R2, R3, R4, R5, R7, R8, and R9 are each as defined above, but where at least one of the radicals R7/R8 represents hydrogen and at least one further radical R7/R8 in a position vicinal to the first represents halogen are reacted with an acid acceptor, if appropriate in the presence of a diluent.