Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-03-05
2003-05-20
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...
C548S262200, C548S263800, C548S267600, C548S267800, C548S268600, C548S269400
Reexamination Certificate
active
06566383
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel sulphonyltriazole derivatives, to a process for their preparation and to their use for controlling undesirable microorganisms.
BACKGROUND OF THE INVENTION
It is already known that certain benzotriazole derivatives have fungicidal properties (cf. DE-A 195 23 446). Thus, for example, 1-(3,5-dimethyl-isoxazole-4-sulphonyl)-1H-benzotriazole can be used for controlling fungi. The activity of this substance is good; however, it is sometimes unsatisfactory at low application rates.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel sulphonyltriazole derivatives of the formula
in which
Hal represents fluorine, chlorine or bromine,
R
1
represents hydrogen, alkyl alkoxyalkyl, cycloalkyl, alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy or represents optionally substituted heterocyclyl and
R
2
represents alkyl or represents optionally substituted heterocyclyl or represents a radical of the formula
in which
R
3
represents halogen, alkyl or phenyl,
R
4
represents hydrogen or alkyl and
R
5
represents alkyl or optionally substituted phenyl, or
R
4
and R
5
together with the nitrogen atom to which they are attached form a heterocyclic ring which may be substituted and may also contain an additional heteroatom.
Furthermore, it has been found that sulphonyltriazole derivatives of the formula (I) are obtained when triazoles of the formula
in which
R
1
and Hal are as defined above,
are reacted with sulphonyl halides of the formula
R
2
—SO
2
—Hal
1
(III)
in which
R
2
is as defined above and
Hal
1
represents chlorine or bromine,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the sulphonyltriazole derivatives of the formula (I) have very good microbicidal properties and can be used for controlling undesirable microorganisms in crop protection and in agriculture.
Surprisingly, the sulphonyltriazole derivatives of the formula (I) according to the invention have considerably better fungicidal activity than 1-(3,5-dimethyl-isoxazole-4-sulphonyl)-1H-benzotriazole, which is a known active compound of the same direction of action and of similar constitution.
The sulphonyltriazole derivatives according to the invention are in each case defined substances; however, their structure cannot always be defined unambiguously. They can be present as compounds of one of the formulae
The notation chosen for the formula (I) is meant to indicate that the positions of the double bonds in the triazole ring and the point of attachment of the —SO
2
—R
2
group cannot always be determined unambiguously.
The formula (I) provides a general definition of the substances according to the invention.
Hal also preferably represents fluorine, chlorine or bromine.
R
1
preferably represents hydrogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl having 1 to 6 carbon atoms in the alkoy moiety and 1 to 6 carbon atoms in the alkyl moiety, cycloalkyl having 3 to 8 carbon atoms or represents alkylaminocarbonyl having 1 to 6 carbon atoms in the alkyl moiety, or
R
1
represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-halogenoalkyl having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenalkylthio having 1 to 5 identical or different halogen atoms, cyano and cycloalkyl having 3 to 6 carbon atoms, or
R
1
represents phenoxy which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-halogenoalkyl having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkylthio having 1 to 5 identical or different halogen atoms, cyano and cycloalkyl having 3 to 6 carbon atoms, or
R
1
represents a heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or sulphur, where this radical may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, hydroxyl, 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, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, carbamoyl, alkyaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety, dialkylaminocarbonyl having 1 to 4 carbon atoms in the individual alkyl moieties, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties and cycloalkyl having 3 to 6 carbon atoms.
R
2
preferably represents alkyl having 1 to 6 carbon atoms or represents a heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or sulphur, where this radical may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, hydroxyl, 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 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, carbamoyl, alkyaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety, dialkylaminocarbonyl having 1 to 4 carbon atoms in the individual alkyl moieties, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties or cycloalkyl having 3 to 6 carbon atoms.
R
2
furthermore preferably represents a radical of the formula
R
3
preferably represents fluorine, chlorine, bromine, alkyl having 1 to 6 carbon atoms or represents phenyl.
R
4
preferably represents hydrogen or alkyl having 1 to 6 carbon atoms.
R
5
preferably represents alkyl having 1 to 6 carbon atoms or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-halogenoalkyl having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogeno-alkylthio having 1 to 5 identical or different halogen atoms, cyano and cycloalkyl having 3 to 6 carbon atoms.
R
4
and R
5
furthermore also together with the nitrogen atom to which they are attached preferably represent a saturated heterocyclic ring having 5 or 6 ring members, where the ring may contain a further nitrogen or oxygen atom and may be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms.
Hal also particularly preferably represents fluorine, chlorine or bromine.
R
1
particularly preferably represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, represents alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, represents cycloalkyl having 3 to 7 carbon atoms or represents alkylaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety, or
R
1
particularly preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethy
Assmann Lutz
Hillebrand Stefan
Stenzel Klaus
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Henderson Richard E. L.
Morris Patricia L.
Mrozinski, Jr. John E.
LandOfFree
Sulfonyltriazol derivatives and their use for combating... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Sulfonyltriazol derivatives and their use for combating..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Sulfonyltriazol derivatives and their use for combating... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3050670