Substituted 1-arylpyrazoles

Details Substituted 1-arylpyrazoles Substituted 1-arylpyrazoles

1997-12-03

2002-01-01

Stockton, Laura L. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S404000, C514S407000, C546S276100, C546S256000, C546S279100, C548S364100, C548S367700, C548S368400, C504S253000, C504S282000

Reissue Patent

active

RE037495

ABSTRACT:

The invention relates to new substituted 1-arylpyrazoles, to a plurality of processes for their preparation, and to their use as pesticides.
It has already been disclosed that certain substituted 1-arylpyrazoles, such as, for example, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-3-cyano-4-[(trifluoromethyl)-sulphinyl]-1H-pyrazole, have a good activity against pests (cf. for example EP-A 295 117 and EP-A 352 944).
Moreover, a large number of substituted 1-arylpyrazoles are described which can be employed for combating pests (cf. for example EP-A 201 852, EP-A 418 016).
In addition, substituted 1-arylpyrazoles are also used as intermediates for the preparation of pesticides (cf. for example EP-A 301 338, EP-A 301 339, EP-A 374 061, EP-A 260 521).
However, the level and duration of action of the previously known compounds is not entirely satisfactory in all fields of application, in particular in the case of certain insects or when low application concentrations are used.
New substituted 1-arylpyrazoles of the general formula (I)
in which
R
1
represents hydrogen, cyano, alkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl or cyanoalkyl,
R
2
represents difluoroethyl or trifluoroethyl,
R
3
represents hydrogen, amino, halogen or one of the following groups
in which
R
4
represents alkyl, halogenoalkyl, alkoxyalkyl or optionally substituted phenyl,
R
5
represents hydrogen or alkyl,
R
6
represents hydrogen, alkyl or optionally substituted phenyl and
R
7
represents alkyl or
R
5
and R
6
together with the carbon atom to which they are bonded represent an optionally substituted heterocycle,
Ar represents optionally substituted phenyl or pyridyl and
n represents a number 0, 1 or 2,
have now been found.
Furthermore, it has been found that the new substituted 1-arylpyrazoles of the general formula (I) are obtained by one of the processes described below:
a) Substituted 1-aryl-4-mercapto-pyrazoles of the formula (Ia)
in which
R
1
, R
2
, Ar and n have the abovementioned meaning and R
3-1
represents hydrogen or amino, are obtained when pyrazole derivatives of the formula (II)
in which
R
1
, R
3-1
and Ar have the abovementioned meanings, are reacted with sulphenyl halides of the formula (III)
R
2
—S—Hal   (III)
in which
R
2
has the abovementioned meaning and Hal represents halogen, in particular chlorine or bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
b) Substituted 1-arylpyrazoles of the formula (Ib)
in which
R
1
, R
2
, R
3-1
have the abovementioned meanings and
n represents the number 1 or 2,
are obtained when compounds of the formula (Ia)
in which
R
1
, R
2
and R
3-1
have the abovementioned meanings,
are oxidized using oxidants, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Other preparation methods for the compounds of the formula (I) according to the invention are given hereinbelow by way of example, but not by limitation, R
1
, R
2
, R
4
, R
5
, R
6
, R
7
, Ar and n having the abovementioned meaning:
c) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with acid halides of the formula (IV) (Hal=chlorine):
d) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with acetals of the formula (V) (R
8
=alkyl):
e) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with tetrahydrofuran derivatives of the formula (VI) (R
8
=alkyl):
f) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with aldehydes or ketones of the formula (VII):
g) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with ortho esters of the formula (VIII):
h) Reaction of substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with tribromomethane, of the formula (IX):
i) Reaction of Substituted 1-arylpyrazoles of the formula (Ic) (R
3-1
=NH
2
) with nucleophiles NU:
The invention preferably relates to compounds of the formula (I) in which
R
1
represents hydrogen, cyano, (C
1
-C
6
)-alkyl, (C1-C4)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
) -halogenoalkyl or (C
1
-C
2
)-cyanoalkyl,
R
2
represents difluoroethyl or trifluoroethyl,
R
3
represents hydrogen, amino, halogen or one of the following groups
in which
R
4
represents (C
1
-C
6
)-alkyl, (C
1
-C
6
)-halogenoalkyl having 1-3 halogen atoms, (C
1
-C
6
)-alkoxy-(C
1
-C
6
)-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,
R
5
represents hydrogen or (C
1
-C
6
)-alkyl,
R
6
represents hydrogen, (C
1
-C
6
)-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,
R
7
represents (C
1
-C
6
)-alkyl or
R
5
and R
6
together with the carbon atom to which they are bonded represent optionally substituted pyridyl,
Ar represents phenyl or pyridyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising halogen, halogeno (C
1
-C
6
)alkyl, halogeno(C
1
-C
6
)alkylthio, halogeno(C
1
-C
6
)alkoxy, alkoxy, hydrazino, (C
1
-C
6
)-dialkylhydrazino, amino, amino(C
1
-C
6
)alkyl, diamino(C
1
-C
6
)alkyl, imino(C
1
-C
6
)-alkyl, cyano, (C
1
-C
6
)alkylthio or the group
in which
R
9
and R
10
are identical or different and represent hydrogen or (C
1
-C
6
)-alkyl, and
n represents a number 0, 1 or 2.
In particular, the invention relates to compounds of the formula (I) in which
R
1
represents hydrogen, cyano, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy-(C
1
-C
2
)-alkyl, (C
1
-C
2
)-halogenoalkyl having 1 to 5 identical or different fluorine, chlorine or bromine atoms, or cyanomethyl,
R
2
represents difluoroethyl or trifluoroethyl,
R
3
represents hydrogen, amino, bromine or one of the following groups
in which
R
4
represents (C
1
-C
4
)-alkyl, (C
1
-C
4
)-halogenoalkyl having 1-3 halogen atoms, (C
1
-C
4
) -alkoxy-(C
1
-C
2
)-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,
R
5
represents hydrogen or (C
1
-C
4
)-alkyl,
R
6
represents hydrogen, (C
1
-C
4
)-alkyl, phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, or 4-hydroxy-3-methoxy-phenyl,
R
7
represents (C
1
-C
4
)-alkyl or
R
5
and R
6
together with the carbon atom to which they are bonded represent optionally substituted pyridyl,
Ar represents phenyl or pyridyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising fluorine, chlorine, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, iminomethyl, cyano, methylthio or the group
in which
R
9
and R
10
are identical or different and represent hydrogen or (C
1
-C
4
)-alkyl, and
n represents a number 0, 1 or 2.
Very particularly preferred compounds of the formula (I) are those in which
R
1
represents hydrogen, cyano, (C
1
-C
4
)-alkyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, bromomethyl or cyanomethyl,
R
2
represents 1,1-difluoroethyl or 2,2,2-trifluoroethyl,
Ar represents phenyl which is disubstituted or trisubstituted by identical or different substituents, substituents in the 2-position being fluorine or chlorine, in the 4-position trifluoromethyl and in the 6-position fluorine, chlorine, cyano, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or
Ar represents a 2-pyridyl radical which is substituted in the 4-position by trifluoromethyl and in the 6-position by fluorine or chlorine, and
R
3
and n have the abovementioned meanings.
The abovementioned general definitions or those where preferred ranges have been mentioned apply to the end products of the formula (I) and, analogously, to the starting materials or intermediates required in each case for the preparation. The definitions can be combined with each other, t

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