Use of 5-amino-pyrazol-derivatives for combating...

Details Use of 5-amino-pyrazol-derivatives for combating... Use of 5-amino-pyrazol-derivatives for combating...

2001-02-20

2002-09-03

Rotman, Alan L. (Department: 1625)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C548S371400, C548S372500, C548S376100

Reexamination Certificate

active

06444612

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the use of 5-amino-pyrazole derivatives, some of which are known, for controlling undesirable microorganisms.
BACKGROUND OF THE INVENTION
It is already known that certain 5-amino-pyrazole derivatives are suitable for controlling animal pests (cf. WO-A 96-21 653). However, the use of these substances against undesirable microorganisms has hitherto not been described.
SUMMARY OF THE INVENTION
5-Amino-pyrazole derivatives of the formula
wherein R
1
, R
2
, R
3
, R
4
, R
5
and Y are defined may be used for controlling undesirable microorganisms.
DETAILED DESCRIPTION
It has now been found that 5-amino-pyrazole derivatives of the formula
in which
R
1
represents alkyl, cycloalkyl, alkoxyalkyl or halogenoalkyl,
R
2
represents hydrogen, halogen, cyano, nitro, halogenoalkylthio, aikoxycarbonyl or alkenyloxycarbonyl,
R
3
represents optionally substituted alkyl or optionally substituted cycloalkyl,
R
4
represents hydrogen, alkyl or optionally substituted cycloalkyl,
Y represents optionally substituted alkanediyl or alkenediyl and
R
5
represents optionally substituted aryl or optionally substituted aryloxy,
are highly suitable for controlling undesirable microorganisms, both in crop protection and in the protection of materials.
Surprisingly, the 5-amino-pyrazole derivatives of the formula (I) which can be used according to the invention exhibit considerably better microbicidal activity than the constitutionally most similar prior-art substances of the same direction of action.
The formula (I) provides a general definition of the 5-amino-pyrazole derivatives which can be used according to the invention.
R
1
preferably represents alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in the alkyl moiety and 1 to 4 carbon atoms in the alkoxy moiety or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,
R
2
preferably represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethylthio, difluoromethylthio, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety or represents alkenyloxycarbonyl having 2 to 4 carbon atoms in the alkenyloxy moiety,
R
3
preferably represents optionally cyano-substituted alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms,
R
4
preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms,
Y preferably represents alkanediyl having 1 to 4 carbon atoms which is optionally mono- or disubstituted by halogen and/or cycloalkyl having 3 to 6 carbon atoms and
R
5
preferably represents phenyl or phenoxy, where each of these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano, C
1
-C
12
-alkyl, C
1
-C
12
-alkoxy, C
1
-C
12
-alkylthio, C
1
-C
12
-halogenoalkyl, C
1
-C
12
-halogenoalkoxy, C
1
-C
12
-halogenoalkylthio, C
2
-C
12
-alkenyl, C
1
-C
4
-alkoxy-C
2
-C
12
-alkenyl, C
1
-C
4
-alkylthio-C
2
-C
12
-alkenyl, C
2
-C
12
-halogenoalkenyl, carboxyl, 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, alkenyloximinoalkyl having 2 to 4 carbon atoms in the alkenyloxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 6 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety, or by phenyl, phenoxy, phenylthio, benzyl, benzyloxy and/or pyridyloxy, where the six lastmentioned radicals for their part may be mono- to trisubstituted by identical or different radicals from the group consisting of halogen, nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy and C
1
-C
4
-halogenoalkylthio,
or
R
5
preferably represents phenyl or phenoxy, where each of these radicals is monosubstituted by a radical of the formula
 in which
R
6
represents phenyl or pyridyl, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,
or
R
5
represents phenyl or phenoxy, where each of these radicals is monosubstituted by a radical of the formula
 in which
R
7
represents alkyl having 1 to 6 carbon atoms or alkoxyalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
or
R
5
represents phenyl or phenoxy, where each of these radicals is monosubstituted by a radical of the formula
 in which
R
8
represents alkyl having 1 to 6 carbon atoms, benzyl or pyridylmethyl, where the two lastmentioned radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,
or
R
5
represents a radical of the formula
R
1
particularly preferably represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl, cyclopropyl, represents methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, 1-chloro-1-ethyl or 1-fluoro- 1-ethyl.
R
2
particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl or allyloxycarbonyl.
R
3
particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents 2-cyanoethyl, cyclopropyl, cyclopentyl or cyclohexyl, where the three lastmentioned radicals may be mono- to trisubstituted by identical or different radicals from the group consisting of fluorine, chlorine, methyl and ethyl.
R
4
particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-, i-, s- or t-butyl or represents cyclopropyl, cyclopentyl or cyclohexyl, where the three lastmentioned radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chorine, methyl and ethyl.
Y particularly preferably represents a grouping of the formula
—CH
2
—, —CH(CH
3
)—, —CH
2
CH
2
—, —CH(C
2
H
5
)—, —CH(C
3
H
7
-i)—, —CHF—, CHCl——CH(cyclopropyl)— or —CH═CH—.
R
5
particularly preferably represents phenyl or phenoxy, where each of these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy, methylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethyithio, carboxyl, hydroximinoalkyl having 1 or 2 carbon atoms in the alkyl moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 or 2 carbon atoms in the alkyl moiety, alkenyloximninoalkyl having 2 to 4 carbon atoms in the alkenyloxy moiety and 1 or 2 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety, or by phenyl, phenoxy, phenylthio, benzyl, benzyloxy and/or pyridyloxy, where the six lastmentioned radicals for their part may be mono- to trisubstituted by identic

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