Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-01-30
2002-02-26
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...
C548S302100
Reexamination Certificate
active
06350770
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel nitrophenyl-sulphonyl-imidazoles, a process for their preparation and their use for controlling vegetable and animal pests.
BACKGROUND OF THE INVENTION
It has already become known that specific phenylsulphonyl-imidazoles and phenylsulphonyl-benzimidazoles have fungicidal properties (cf. EP-A 0 238 824 and WO 97-06 171). Thus, 1-(2-methyl-5-nitro-phenylsulphonyl)-benzotriazole, 2-methyl-1-(2-methyl-5-nitro-phenylsulphonyl)-imidazole and 1-(2-methyl-5-nitro-phenylsulphonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5-f]-benzimidazole can be used for controlling fungi. The activity of these substances is good but is unsatisfactory in some cases at low application rates.
Novel nitrophenyl-sulphonyl-imidazoles of the formula
in which
a) X represents cyano,
R
1
represents halogen, alkyl or phenyl,
R
2
represents halogen, alkyl or phenyl or
R
1
and R
2
, together with the carbon atoms to which they are bonded, represent an optionally substituted benzene ring or represent an optionally substituted heterocyclic ring and
R
3
represents halogen, alkyl or phenyl or
b) X represents halogen,
R
1
represents halogen, alkyl or phenyl,
R
2
represents halogen, alkyl or phenyl or
R
1
and R
2
, together with the carbon atoms to which they are bonded, represent an optionally substituted heterocyclic ring or
R
1
and R
2
, together represent a doubly bonded radical of the formula
and
R
3
represents halogen, alkyl or phenyl,
have now been found.
It has furthermore been found that nitrophenyl-sulphonyl-imidazoles of the formula (I) are obtained if imidazole derivatives of the formula
in which
R
1
, R
2
and X have the abovementioned meanings,
are reacted with nitrobenzene-sulphonyl halides of the formula
in which
R
3
has the abovementioned meaning and
Hal represents chlorine or bromine,
optionally in the presence of an acid acceptor and optionally in the presence of a diluent.
Finally, it has been found that the nitrophenyl-sulphonyl-imidazoles of the formula (I) are very suitable for controlling vegetable and animal pests in crop protection and in material protection. Surprisingly, the substances according to the invention exhibit a better fungicidal activity than 1-(2-methyl-5-nitro-phenylsulphonyl)-benzotriazole and 2-methyl-1-(2-methyl-5-nitro-phenylsulphonyl)-imidazole, which are constitutionally similar, previously known active substances having the same type of activity.
The substances according to the invention are generally defined by the formula (I).
A preferred group of substances according to the invention are nitrophenyl--sulphonyl-imidazoles of the formula
Here, the substituents preferably have the meanings stated below.
R
1
preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.
R
2
preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.
R
1
and R
2
, together with the carbon atoms to which they are bonded, furthermore preferably represent a benzene ring which can be monosubstituted to trisubstituted, identically or differently, by
halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio or alkylsulphonyl, each having 1 to 5 carbon atoms;
halogenoalkyl, halogenoalkoxy, halogenoalkylthio or halogenoalkylsulphionyl, each having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;
halogenoalkenyl or halogenoalkenyloxy, each of which is straight-chain or branched and each of which has 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;
alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydrox-iminoalkyl, alkoximinoalkyl or cyanoimino(alkoxy)alkyl, each having 1 to 4 carbon atoms in the individual alkyl moieties;
cycloalkyl having 3 to 6 carbon atoms;
phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and/or pyridylthio, it being possible for each of these radicals to be monosubstituted or disubstituted, identically or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and/or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
R
1
and R
2
, together with the carbon atoms to which they are bonded, furthermore preferably represent a benzene ring which is substituted by doubly linked alkylene having 3 or 4 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, it being possible for the alkylene or dioxyalkylene groups to be monosubstituted to tetrasubstituted, identically or differently, by halogen, alkyl having 1 to 4 carbon atoms and/or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms.
R
1
and R
2
, together with the carbon atoms to which they are bonded, furthermore preferably represent a 5- or 6-membered heterocyclic ring which contains one, two or three identical or different heteroatoms, such as oxygen, sulphur and/or nitrogen, and may be monosubstituted to trisubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, 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 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and/or halogenoalkylcarbonyloxy having 1 to 4 carbon atoms in the halogenoalkyl group and 1 to 5 identical or different halogen atoms, the oxygen atoms not being adjacent where the heterocyclic ring contains more than one oxygen atom.
R
3
preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.
A further group of preferred substances according to the invention are nitrophenyl-sulphonyl-imidazoles of the formula
In this formula, the substituents preferably have the meanings stated below.
Hal
1
preferably represents fluorine, chlorine or bromine.
R
1
preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.
R
2
preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.
R
1
and R
2
, together with the carbon atoms to which they are bonded, furthermore preferably represent a 5- or 6-membered heterocyclic ring which contains one, two or three identical or different heteroatoms, such as oxygen, sulphur and/or nitrogen, and may be monosubstituted to trisubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, 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 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbo
Assmann Lutz
Erdelen Christoph
Kugler Martin
Stenzel Klaus
Wachtler Peter
Bayer Aktiengesellschaft
Gil Joseph C.
Morris Patricia L.
LandOfFree
Nitrophenyl-sulfonyl-imidazoles and use thereof for... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Nitrophenyl-sulfonyl-imidazoles and use thereof for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nitrophenyl-sulfonyl-imidazoles and use thereof for... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2934567