Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1994-08-24
1997-03-18
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544321, C07D23947, A01N 4354
Patent
active
056122861
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP93/00362, filed Feb. 16, 1993.
The present invention relates to N-[(pyrimidin-2-yl)amincarbonyl]benzenesulfonamides of the general formula I ##STR2## where R.sup.1 is methyl or ethyl; methoxy groups or fluorine atoms; -alkyl, which may carry from 1 to 3 or 1 to 5 fluorine atoms, with the exception of difluoromethoxy, and, if E is O and at the same time R.sup.5 is trifluoromethyl, R.sup.6 may furthermore be methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, allylsulfonyl or propargylsulfonyl; methylthio, ethylthio or C.sub.1 -C.sub.2 -haloalkoxy;
The present invention furthermore relates to a process for the preparation of the compounds I and to their use as herbicides.
The prior art includes a number of patents which relate to sulfonylureas having a herbicidal action.
EP-A 44 808 lists the compounds A-D in the form of a table, without further characterization. ##STR3##
The sulfonylurea E is mentioned in EP-A 44 807, likewise without physical characteristics. ##STR4##
EP-A 338 424 describes methyl benzoates, for example F. ##STR5##
DE-A 39 00 172 relates to benzoates and benzamides and o-halogen-substituted sulfonylureas, for example having the structures G-I. ##STR6##
EP-A 101 308 describes higher sulfones, for example J-M. ##STR7##
U.S. Pat. No. 4,120,691 (DE-A 27 15 786) mentions the sulfonylureas N and O. ##STR8##
U.S. Pat. No. 4,310,346 discloses sulfonamides having the structure P. ##STR9##
Dimethylcarbamoyl-substituted sulfonylureas having the structure R ##STR10## are disclosed in U.S. Pat. No. 4,515,624.
Sulfonylurea derivatives substituted by fluoroalkoxy, sulfamoyl, acyl or alkyl in the ortho position of the phenyl radical are represented by general structural formulae in EP-A 173 312, U.S. Pat. Nos. 4,515,624, 4,425,153 and EP-A 44 209, respectively, without any detailed information on specific structures.
The earlier German Applications P 40 38 430.6 of Dec. 1, 1990 and P 41 05 518.7 of Feb. 22, 1991 describe herbicidal sulfonamides which, compared with the novel compounds, have different substituents in the ortho position of the phenyl radical and/or in the 3/5 positions of the triazine radical.
It is an object of the present invention to synthesize sulfonylureas which have improved properties compared with the known members of this herbicide class.
We have found that this object is achieved by the N-[(pyrimidin-2-yl)aminocarbonyl]benzenesulfonamides of the formula I which are defined at the outset.
In view of their intended use, suitable substituents are, for example, the following radicals: isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, which may carry from one to three methoxy groups or fluorine atoms; -alkyl, which if R.sup.6 is methyl may carry 1 to 3 fluorine atoms and if R.sup.6 is ethyl may carry 1 to 5 fluorine atoms, with the exception of difluoromethoxy, and, if E=O and at the same time R.sup.5 =trifluoromethyl, R.sup.6 may furthermore be methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, allylsulfonyl or propargylsulfonyl; diethylaminosulfonyl if R.sup.5 is fluorine; where up to three hydrogen atoms may be replaced by halogen atoms; methylthio, ethylthio or C.sub.1 -C.sub.2 -haloalkoxy such as trifluoromethoxy or difluoromethoxy; and
Halogen is in general fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Compounds with R.sup.1 =methyl and R.sup.2 =hydrogen are preferred.
Preferred definitions of R.sup.3 are: methylsulfonyloxy, trifluoromethyl, trifluoromethoxy, thiomethyl, nitro, methylsulfonyl, ethylsurfonyl, methoxymethyl and N,N-dimethylsulfamoyl.
Particularly preferred compounds I arise as a result of the following combinations of radicals: R.sup.5 =trifluoromethyl; =trifluoromethyl or fluorine; =trifluoromethyl or fluorine; =6-methylthio, R.sup.5 =trifluoromethyl or fluorine; =trifluoromethyl or fluorine; =trifluoromethyl or fluorine; R.sup.5 =trifluoromethyl or fluorine; R.sup.5 =fluorine.
The novel sulfonylureas of the formula I are obtainable by various methods which are described in the literature.
REFERENCES:
patent: 4120691 (1978-10-01), Levitt
patent: 4169719 (1979-10-01), Levitt
patent: 4310346 (1982-01-01), Levitt et al.
patent: 4425153 (1984-01-01), Adams, Jr.
patent: 4515624 (1985-05-01), Reap
Mayer et al., Chemical Abstracts, vol. 118, entry 6988 (1992).
Levitt, Chemical Abstracts, vol. 92, entry 111047 (1979).
Levitt, Chemical Abstracts, vol. 88, entry 6395 (1977).
Gerber Matthias
Hamprecht Gerhard
Kardorff Uwe
Mayer Horst
Walter Helmut
BASF - Aktiengesellschaft
Ford John M.
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