Sulfonylurea derivatives and their use

Details Sulfonylurea derivatives and their use Sulfonylurea derivatives and their use

1993-08-06

1995-07-18

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544321, 544323, 544332, C07D23969, C07D23948, A01N 4354

Patent

active

054341248

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP92/00182, filed Jan. 29, 1992.

The present invention relates to substituted sulfonylurea derivatives of the general formula I ##STR2## where R.sup.1 is C.sub.1 -C.sub.4 -alkyl which may carry up to three of the following radicals: halogen or C.sub.1 - or C.sub.2 -alkoxy; C.sub.2 - or C.sub.3 -alkenyl; propargyl; C.sub.1 -C.sub.3 -alkylamino; di-C.sub.1 -C.sub.4 -alkylamino or phenyl which may carry up to three of the following radicals: halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 - or C.sub.2 -alkoxy; carry from 1 to 3 halogen atoms, or C.sub.1 - or C.sub.2 -alkylsulfonyl, nitro or cyano; chlorodifluoromethoxy or fluorine; - or C.sub.2 -haloalkoxy, methoxy, ethoxy, methylamino or dimethylamino; or C.sub.3 - or C.sub.4 -alkynyl and not alkylsulfonyl and R.sup.4 is not methyl or methoxy and agriculturally useful salts thereof.
The present invention furthermore relates to processes for the preparation of the stated compounds of the general formula I and to their use as herbicides.
European Patents EP-B 30 433, 44 212, 125 205, 135 332, 136 061 and 158 600 and U.S. Pat. Nos. 4,534,789 and 4,127,405 describe unsubstituted or substituted alkyl- or arylsulfonates and EP-A 125 205 and U.S. Pat. Nos. 4,576,633 and 4,515,624 describe unsubstituted or substituted aminosulfonates based on sulfonylurea, as herbicides. However, they do not meet all requirements with regard to activity and selectivity.
End products of the formula I which are preferred because of the biological activity are those of the formula I where isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, preferably methyl or ethyl, bromomethyl, 2-fluoroethyl, 2-chloroethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl or 2,2,2-trichloroethyl, preferably 2,2,2-trifluoroethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl or 3-ethoxypropyl, preferably methoxymethyl, ethoxymethyl or 2-methoxyethyl, propargyl, 1-propen-1-yl, preferably vinyl or 1-propen-3-yl, isopropylamino, preferably methylamino, di-C.sub.1 -C.sub.4 -alkyl, such as dimethyl-, diethyl-, di-n-propyl-, di-isopropyl-, di-tert-butyl-, methylethyl- or methylisopropylamino, preferably dimethylamino, aryl, such as phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-tolyl, 3-tolyl, 4-tolyl, 2-tert-butylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2-anisyl, 3-anisyl, 4-anisyl, 2-ethoxyphenyl, 3-ethoxyphenyl or 4-ethoxyphenyl, preferably phenyl, 4-tolyl or 4-anisyl, ethoxy, nitro, cyano, trichloromethyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl, preferably hydrogen, fluorine, chlorine, methyl or methoxy, fluorine, ethyl, trifluoromethyl, 1,1,1-trifluoroethyl, difluoromethoxy, trifluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, methylamino or dimethylamino, preferably methoxy, chlorine, fluorine, methyl, trifluoromethoxy, chlorodifluoromethoxy or trifluoromethyl, and 1-propen-3-yl, propargyl or 2-butyn-1-yl, preferably hydrogen, methyl or 1-propen-3-yl.
The novel sulfonylureas of the formula I are obtainable by various methods which are described in the literature. Particularly advantageous methods (A-D) are described in detail below by way of example. ##STR3## A: A sulfonyl isocyanate II is reacted in a conventional manner (EP-A-162 723 or EP-A-44 212) with about the stoichiometric amount of a 2-amino- 1,3,5-triazine or -pyrimidine derivative III at from 0.degree. to 120.degree. C., preferably from 10.degree. to 100.degree. C. The reaction can be carried out under atmospheric or superatmospheric pressure (up to 50 bar), preferably at from 1 to 5 bar, continuously or batchwise.
Solvents and diluents which are inert under the particular reaction conditions are advantageously used for the reactions. Examples of suitable solvents are halohydrocarbons, in particular chlorohydrocarbons, eg. tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, di

REFERENCES:
patent: 4127405 (1978-11-01), Levitt
patent: 4435205 (1984-03-01), Reap
patent: 4515624 (1985-05-01), Reap
patent: 4534789 (1985-08-01), Reap
patent: 4576633 (1986-03-01), Reap
patent: 4835311 (1989-05-01), Gass et al.

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