Process for the preparation of N,N'-substituted ureas

A process for the manufacture of compounds of the formula V ##STR11## wherein X.sub.1 is S or O, X.sub.2 is N or CH, Y is H, Cl, F or Br,

• R.sub.1 is H, F, Cl, Br or --COOR.sub.3,
• R.sub.2 is --COO(C.sub.1 -C.sub.4 -alkyl), --(CO)R.sub.3 or C.sub.1 -C.sub.2 -alkyl which is unsubstituted or substituted by halogen atoms, and
• R.sub.3 is H or C.sub.1 -C.sub.4 -alkyl,
• R.sub.8 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy
• R.sub.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, and
• R.sub.10 is H, halogen, NH.sub.2, NH(C.sub.1 -C.sub.3 alkyl), NH(C.sub.1 -C.sub.3 alkyl).sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl,
• C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, by
• a) reacting in a first step 1 mole equivalent of a compound of the formula IIb ##STR12## wherein X.sub.3 represents hydroxyl, --OM or --O(M.sub.1).sub.1/2, where M is an alkali metal atom or a tertiary ammonium group, having from 3 to 18 carbon atoms, and M.sub.1 is an alkaline earth metal atom, with at least 1 mole equivalent of a compound of formula IIIb
• CHR.sub.1 .dbd.CHR.sub.2 (IIIb),
• optionally in the presence of an inert solvent, and in the presence of a catalytic amount of a homogeneous palladium catalyst and a base selected from alkali metal salts, alkaline earth metal salts and a tertiary ammonium salt of a carboxylic acid to give a compound of the formula IVb ##STR13## and b) hydrogenating in a second step the compound of the formula IVb optionally in the presence of an inert solvent and in the presence of catalytic amounts of a hydrogenation catalyst, to form a compound of the formula Ib ##STR14## c) reacting in a third step the compound of formula Ib with at least 1 mole of a halogenating agent to form the sulfochloride, which is then reacted with NH.sub.3 to give the sulfonamide of the formula Ic ##STR15## d) reacting the compound of the formula Ic with COCl.sub.2 or CSCl.sub.2 to obtain a compound of the formula VI ##STR16## e) reacting the compound of the formula VI with a compound of the formula VII ##STR17## to form the compound of the formula V, characterised in that the homogeneous palladium catalyst is reduced to insoluble palladium metal in the step a) reaction mixture, which is subsequently used as the heterogeneous hydrogenation catalyst.