Process for producing sulfonylureas having a herbicidal action

Claim 1

A process for producing sulfonylureas which have a herbicidal action and an action regulating plant growth, and which correspond to the formula I ##STR24## wherein A is a radical of the formula ##STR25## Y is oxygen, sulfur or ##STR26## R 1 is hydrogen, halogen, nitro, trifluoromethyl, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, --COR 7 , --S(O) m --C 1 -C 5 -alkyl, --SO 2 R 10 , XR 11 or --OSO 2 C 1 -C 5 -alkyl, R 2 is hydrogen, fluorine, chlorine, bromine, nitro, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, trifluoromethyl, C 1 -C 5 -haloalkoxy or --COR 7 , R 3 is hydrogen, fluorine, chlorine, bromine, nitro, methoxy or trifluoromethyl, R 4 is hydrogen, halogen, nitro, C 1 -C 5 -alkyl, methoxy, --COR 7 or --SO 2 NR 8 R 9 , R 5 is hydrogen, fluorine, chlorine, bromine, nitro, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, trifluoromethyl, --S(O) m C 1 -C 5 -alkyl, --COR 7 or --SO 2 NR 8 R 9 , R 6 is hydrogen, fluorine, methyl or methoxy, R 7 is hydrogen, C 1 -C 5 -alkyl, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkoxy, C 1 -C 5 -haloalkoxy, C 2 -C 10 -alkoxyalkoxy, C 3 -C 5 -alkenyloxy, C 3 -C 5 -alkynyloxy, phenoxy, benzyloxy, C 1 -C 5 -alkylthio or --NR 8 R 9 , R 8 is hydrogen, C 1 -C 5 -alkyl, cyanoalkyl having a maximum of 5 carbon atoms, methoxy, ethoxy or C 3 -C 5 -alkenyl, R 9 is hydrogen, C 1 -C 5 -alkyl or C 3 -C 5 -alkenyl, or R 8 and R 9 together with the nitrogen atom binding them form a 5- or 6-membered, saturated heterocycle which can contain an oxygen or sulfur atom as ring member, R 10 is C 1 -C 5 -haloalkoxy or --NR 8 R 9 , R 11 is C 1 -C 5 -alkyl which is substituted by halogen, C 1 -C 5 -alkoxy, --S(O) m C 1 -C 5 -alkyl, --S(O) m C 1 -C 5 -haloalkyl or C 2 -C 5 -alkenyl which can be substituted by one of the above radicals, X is oxygen or --S(O) m --, m is zero, one or two, E is the methine group or nitrogen, R a is hydrogen, halogen, C 1 -C 5 -alkyl, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkoxy, C 1 -C 5 -haloalkoxy, C 1 -C 5 -alkylthio, C 2 -C 10 -alkoxyalkyl or C 2 -C 10 -alkoxyalkoxy, R b is the same as R a or is an amino group ##STR27## wherein R c is hydrogen, methyl or ethyl, and R d is hydrogen, methyl, ethyl or methoxy, and also the salts of these compounds, which process comprises condensing a sulfonyl chloride of the formula II A--SO.sub.2 Cl (II), in an inert phase system or organic solvent, in the presence of at least the equimolar amount of a base as acid-binding agent and at a temperature of 0° to 100° C., with an imidocarbonic acid ester of the formula III ##STR28## in which R x is C 1 -C 5 -alkyl; isolating the formed sulfonylimidocarbonic acid diester of the formula IV ##STR29## reacting it then in an inert solvent in the presence of a strong base, at a temperature of between 0° and 100° C., with a 2-aminopyrimidine or 2-aminotriazine of the formula V ##STR30## to give a sulfonylisourea of the formula VI ##STR31## and subsequently converting this in the presence of a hydrogen halide in an inert solvent, at a temperature of 0°-100° C., into a sulfonylurea of the formula I; and finally isolating this as such or as a salt.