Herbicidal sulfonylureas

Details Herbicidal sulfonylureas Herbicidal sulfonylureas

1994-02-28

1997-01-07

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544321, C07D23952, C07D23969, A01N 4354

Patent

active

055916945

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP92/01879 filed Sep. 25, 1992, and published as WO93/05048 Mar. 18, 1993.
The present invention relates to substituted sulfonylureas of the formula I ##STR2## where n and m are each 0 or 1; C.sub.3 -C.sub.6 -alkynyl; -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl when m i s 1 or trifluoro- or chlorodifluoromethyl when X is O or S and -alkyl; -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkoxy; R.sup.7, a group ER.sup.7, where E is O, S or NR.sup.9, ##STR3## C.sub.1 -C.sub.4 -alkyl which is unsubstituted or mono-, di- or trisubstituted by methoxy, ethoxy, SO.sub.2 CH.sub.3, cyano, thiocyanato or SCH.sub.3, or C.sub.2 -C.sub.4 -alkenyl which is unsubstituted or mono-, di- or trisubstituted by halogen, nitro or cyano; following radicals: halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 - or C.sub.2 -alkoxy, C.sub.3 -C.sub.7 -cycloalkyl and/or phenyl; C.sub.5 -C.sub.7 -cycloalkyl which may carry from one to three C.sub.1 -C.sub.4 -alkyl groups; C.sub.2 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; R.sup.6 is hydrogen, C.sub.1 - or C.sub.2 -alkoxy or C.sub.1 -C.sub.6 -alkyl, or, together with R.sup.7, forms a C.sub.4 -C.sub.6 -alkylene chain in which a methylene group may be replaced with an oxygen atom or a C.sub.1 -C.sub.4 -alkylimino group; or C.sub.4 -alkynyl, it being possible for the stated radicals to carry a further one to four halogen or C.sub.1 -C.sub.4 -alkoxy radicals, or is C.sub.3 -C.sub.6 -cycloalkyl, or where E is NR.sup.9, is furthermore methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, acetyl which may carry one to three halogen atoms, or methoxycarbonyl, dimethylcarbamoyl or dimethylsulfamoyl; or C.sub.2 -alkoxy-C.sub.1 - or C.sub.2 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 - or C.sub.3 -haloalkenyl, or, where p is 1 and q is 0, is furthermore C.sub.1 -C.sub.3 -alkylamino or di-(C.sub.1 - or C.sub.2 -alkyl)-amino,
The present invention furthermore relates to a process for the preparation of the compounds I and to their use as herbicides and intermediates for the preparation of the sulfonylureas I.
U.S. Pat. No. 4,547,215 discloses, as herbicides, various sulfonylureas which are substituted in the pyrimidine moiety by chlorine. EP-A-72 347, 84 020 and 169 815 describe sulfonylureas which are substituted in the pyrimidine moiety by difluoromethoxy or bromodifluoromethoxy. However, these compounds have unsatisfactory selectivity with respect to weeds. Sulfonylureas with different substitution patterns on the phenyl radical are disclosed in the prior Applications EP-A-446 743 and EP-A-469 460.
It is an object of the present invention to provide novel compounds from the class consisting of the sulfonylpyrimidylureas, having improved herbicidal properties.
We have found that this object is achieved by the sulfonylureas defined at the outset.
We have furthermore found that the compounds of the formula I and the alkali and alkaline earth metal salts thereof have good selectivity with respect to weeds in crops such as cereal and corn.
we have also found chemically unique processes for the preparation of the compounds I. In comparison with the prior art, the sulfonylureas I can unexpectedly be prepared in regioselective form and in high yield and purity starting from substituted 2-amino-4-fluoroalkoxy-6-pyrimidines of the general formula IIIa ##STR4## where m is 1 and n is 0 or 1; C.sub.3 -C.sub.6 -alkynyl; -C.sub.6 -alkynyl;
For the preparation of compounds which are halogen-substituted in the pyrimidine moiety (R.sup.2 =Hal, m=0), correspondingly substituted 2-amino-4-fluoroalkoxy-6-halopyrimidines of the structure IIIb are used as starting materials (cf. Scheme 2), the preparation of such pyrimidines being the subject of German Application P 40 07 316 (O.Z. 0050/41451). The pyrimidine intermediates in which m is 0 and R.sup.2 is trifluoromethyl are obtained in a similar manner according to Scheme 3.
The novel sulfonylureas of the formula I are o

REFERENCES:
patent: 4547215 (1985-10-01), Wolf
patent: 5188657 (1993-02-01), Hamprecht
patent: 5276007 (1994-01-01), Hamprecht et al.

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