Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1994-06-17
1996-01-30
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544211, C07D25142, A01N 4366
Patent
active
054880297
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to N-[(1,3,5-traizin-2-yl)-aminocarbonyl]-benzenesulfonamides of the general formula I ##STR2## where R.sup.1 is methyl or ethyl; methoxy groups; -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.3 - or C.sub.4 -alkynyl or C.sub.3 -C.sub.6 -cycloalkyl which may carry from 1 to 3 or from 1 to 5 halogen atoms, with the exception of difluoromethoxy; C.sub.1 - or C.sub.2 -haloalkoxy, fluorine or chlorine, with the exception of 6-chloro and 6-fluoro when R.sup.3 is alkyl or C.sub.1 - or C.sub.2 -alkoxy;
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.
U.S. Pat. No. 4,127,405 describes a triazine compound A and U.S. Pat. No. 4,169,719 the pyrimidine derivative B, which have the most similar structures. ##STR3##
EP-A 44 807 describes two sulfonylureas C having an ortho allyloxy group. ##STR4##
R.dbd.CH.sub.3 or C.sub.2 H.sub.5
EP-A 44 808 describes sulfonylureas D which are substituted by 2-chloroethoxy or difluoromethoxy in the phenyl moiety. ##STR5##
D.sub.1 :
D.sub.2 :
EP-A 48 143 describes two N-methylated sulfonyl-ureas E, which are not further characterized. ##STR6##
Z.dbd.CH or N
EP-A 388 873 relates to benzoates having the structure F. ##STR7##
R.dbd.CH.sub.3 or C.sub.2 H.sub.5
U.S. Pat. No. 4,127,405 discloses sulfonylureas derivatives which are substituted by chlorine or trifluoromethyl in the ortho position of the phenyl ring and by CH.sub.3 /OCH.sub.3 in the triazine ring ##STR8## The compound G is known under the name chlorsulfuron (Glean.RTM.).
Sulfonylurea derivatives substituted by fluoroalkoxy, sulfamoyl, acyl or alkyl in the ortho position of the phenyl radical are represented by general formulae in EP-A 173 212, U.S. Pat. No. 4,515,624, U.S. Pat. No. 4 425 153 and EP-A 44 209, without more detailed information on specific structures being given.
The earlier German Applications WO 92/09608 of Dec. 1, 1990 and Wo 92/14715 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 herbicidal class and in particular exhibit high selectivity in sensitive crops, such as rice or corn.
We have found that this object is achieved by the N-[(1,3,5-traizin-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: isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, which may carry from one to three methoxy groups, such as methoxymethyl or 2-methoxyethyl; 2-chloropropyl, 3-chloropropyl, 4-chlorobutyl, 1,1,2,2,2-pentafluoroethyl, 2,2,2-trifluoroethyl or 1,1-difluoroethyl; -alkyl which may carry from one to three fluorine atoms when R.sup.5 is methoxy and from one to five fluorine atoms when R.sup.5 is ethoxy, with the exception of difluoromethoxy; or C.sub.1 - or C.sub.2 -haloalkoxy, such as C.sub.1 or C.sub.2 -fluoro- or chloroalkoxy, for example trifluoromethoxy, fluorine or chlorine, with the exception of 6-chloro and 6-fluoro when R.sup.3 is alkyl or C.sub.1 - or C.sub.2 -alkoxy; preference is given to compounds I where R.sup.1 is methyl, R.sup.2 and R.sup.4 are each hydrogen and R.sup.3 is trifluoromethoxy, to compounds I where R.sup.1 is methyl, R.sup.2 is hydrogen, R.sup.3 is thiomethyl and R.sup.4 is thiomethyl, in particular 6-thiomethyl, and to compounds I where R.sup.1 is methyl, R.sup.2 and R.sup.4 are each hydrogen and R.sup.3 is nitro or methoxy.
The novel sulfonylureas of the formula I are obtainable by various methods which are described in the literature. Particularly advantageous methods (A-D) are illustrated below by way of example. ##STR9##
A: A sulfonylisocyanate II is reacted in a
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Gerber Matthias
Hamprecht Gerhard
Kardorff Uwe
Mayer Horst
Walter Helmut
BASF - Aktiengesellschaft
Ford John M.
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