Process for producing sulfonylureas having a herbicidal action

Details Process for producing sulfonylureas having a herbicidal action Process for producing sulfonylureas having a herbicidal action

1983-10-14

1985-06-04

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544211, 544212, 544206, 544207, 544208, 544209, 544113, 544122, 544123, 544 96, 544 63, 544 60, 544 55, 544320, 544321, 544324, 544331, 544323, 544330, 544332, C07D25118, C07D25146, C07D25152, C07D23969

Patent

active

045215979

ABSTRACT:
A novel process for producing sulfonylureas of the formula I having a herbicidal action and an action regulating plant growth ##STR1## wherein A is an unsubstituted or substituted phenyl, naphthyl, furan, thiophene or pyridine group, E is a nitrogen atom or the methine group, R.sub.a is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -haloalkoxy, C.sub.1 -C.sub.5 -alkylthio or C.sub.2 -C.sub.10 -alkoxyalkoxy, and R.sub.b is the same as R.sub.a or is an unsubstituted or substituted amino group, and salts thereof, which process comprises firstly condensing an imidocarbonic acid ester with a sulfonyl chloride of the formula II to the sulfonylimidocarbonic acid diester of the formula IV ##STR2## wherein R is an alkyl group, and reacting this in an ethereal solvent in the presence of sodium hydride or potassium tertbutylate with a 2-aminopyrimidine or 2-amino-1,3,5-triazine of the formula V, and finally reacting the formed sulfonylisourea of the formula VI in an organic solvent with hydrochloric acid to obtain the sulfonylurea of the formula I, and isolating this as such or as a salt; ##STR3## The sulfonylimidocarbonic acid diesters of the formula IV and certain sulfonylisoureas of the formula VI, required as intermediates, are novel compounds. The process has the advantage that no sulfonamides are needed as intermediates.

REFERENCES:
patent: 4301286 (1981-11-01), Schwing et al.
patent: 4302241 (1981-11-01), Levitt
Sandmeyer, "Ueber Derivative der Kohlensaure Chlorimidokohlensaureathylester", Ber. 19, 862 (1886).
Auwers et al., "Ueber Symmetrische .alpha..alpha.-Dimethylglutarsauren", Ann 287, 310-311, (1895).
Meyer, "Oxygen-to-Nitrogen Rearrangement of Diethyl N-(p-Tolylsulfonyl) . . . ", J. Org. Chem. 28, 2902-2903, (1963).
Hoth et al., "Organylsilyl-borane", Chem. Ber. 99, 2197-2205, (1966).

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