Organic compounds -- part of the class 532-570 series – Organic compounds – Imidate esters
Patent
1985-03-01
1986-12-16
Jiles, Henry R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Imidate esters
546294, 549 65, 549488, 544197, 544198, 544331, 544330, 544320, C07C11920
Patent
active
046298029
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: 3647861 (1972-03-01), Buchanan
Meyer, J. Org. Chem., 28 (1963), 2902.
300 Band des Archivs der Pharmazie, (1967), pp. 553-559, R. Neidlein und W. Haussmann.
Chem. Ber. 99, 2900 (1966), Keten-Dichloride.sup.(2) und N-Dichlormethylensulfonamide.sup.(3,4), Rudolf Gompper.sup.(1) und Rolf Kunz.
Kristinsson Haukur
Topfl Werner
Ciba-Geigy Corporation
Jiles Henry R.
Mansfield Kevin T.
McC. Roberts Edward
Whittenbaugh Robert C.
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