Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-04-09
2001-01-30
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S221000
Reexamination Certificate
active
06180655
ABSTRACT:
The present invention relates to novel sulphonylbenzazolones, to a process for their preparation and to their use as microbicides in crop protection and in the protection of materials.
TECHNICAL FIELD OF THE INVENTION
It is already known that certain sulphonylbenzazolones have fungicidal properties (cf. DE-A 2 101 150). Thus, for example, N,N-dimethyl-7-nitro-2-oxo-5-trifluoro-methyl-benzothiazole-3-sulphonamide can be used for controlling fungi. The activity of this compound is good, but at times leaves something to be desired at low application rates.
BACKGROUND OF THE INVENTION
Detailed Description of the Invention
This invention, accordingly, provides novel sulphonylbenzazolones of the formula
in which
R
1
, R
2
, R
3
and R
4
independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, represent —Z—K
6
or
in which
R
6
represents optionally substituted aryl or represents optionally substituted heterocyclyl,
z represents a direct bond, represents—CH
2
—, O, S, SO
2
or CO or
represents—CO—O— where the oxygen atom is linked to R
6
, or
represents—SO
2
—O— where the sulphur atom is linked to R
6
, or
represents—S—CH
2
—SO
2
— where the sulphur atom of the thio group is linked to R
6
, or
represents—NH—SO
2
— where the sulphonyl group is linked to R
6
,
R
7
and R
8
independently of one another represent hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted aryl-sulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl or
R
7
and R
8
together with the nitrogen atom to which they are attached represent an optionally alkyl-substituted heterocyclic ring which may contain an additional oxygen atom or an alkylimino group and
W represents a direct bond, a sulphonyl group or a carbonyl group, or
R
1
and R
2
, or R
2
and R
3
, or R
3
and R
4
together each represent an optionally substituted alkylene chain having 3 or 4 members, in which one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms,
R
5
represents optionally substituted unsaturated heterocyclyl and
Q represents oxygen or sulphur.
Furthermore, it was found that sulphonylbenzazolones of the formula (I) are obtained when
benzazolones of the formula
in which
R
1
, R
2
, R
3
, R
4
and Q are each as defined above
are reacted with a sulphonyl halide of the formula
R
5
—SO
2
—X (III)
in which
R
5
is as defined above and
X represents halogen,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it was found that the sulphonylbenzazolones of the formula (I) have very good microbicidal properties and can be employed in crop protection and also in the protection of materials.
Surprisingly, the compounds according to the invention exhibit better fungicidal activity than N,N-dimethyl-7-nitro-2-oxo-5-trifluoromethyl-benzothiazole-3-sulphonamide, an active compound of the prior art having a similar structure and the same direction of action.
Formula (I) provides a general definition of the compounds according to the invention.
R
1
, R
2
, R
3
and R
4
independently of one another each preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to pentasubstituted by identical or different halogens and/or alkyls having 1 to 4 carbon atoms, represents hydroxy-carbonyl, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkoxy moiety, cycloalkylcarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, cycloalkoxycarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, represents —Z—R
6
or
R
6
preferably represents aryl having 6 to 10 carbon atoms, each of these radicals being mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulphinyl having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and/or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
R
6
additionally preferably represents an unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms such as nitrogen, oxygen and/or sulphur, it being possible for these radicals to be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, cyano and/or nitro.
Z also preferably represents a direct bond, and also represents—CH
2
—, O, S, SO
2
or CO or
represents—CO-—O—where the oxygen atom is linked to R
6
, or
represents—SO
2
—O— where the sulphur atom is linked to R
6
, or
represents—S—CH
2
—SO
2
— where the sulphur atom of the thio group is linked to R
6
, or
represents—NH—SO
2
— where the sulphonyl group is linked to R
6
.
R
7
and R
8
independently of one another each preferably represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, aryl having 6 to 10 carbon atoms, arylcarbonyl having 6 to 10 carbon atoms in the aryl moiety, arylsulphonyl having 6 to 10 carbon atoms, arylaminocarbonyl having 6 to 10 carbon atoms in the aryl moiety or represents arylmethylsulphonyl having 6 to 10 carbon atoms in the aryl moiety, it being possible for each of the abovementioned aryl radicals to be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen
Assmann Lutz
Elbe Hans-Ludwig
Markert Robert
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Gil Joseph C.
Morris Patricia L.
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