3-thiocarbamoylpyrazole derivatives as pesticides

Details 3-thiocarbamoylpyrazole derivatives as pesticides 3-thiocarbamoylpyrazole derivatives as pesticides

1999-05-06

2001-07-24

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, C514S406000, C548S364100, C548S367400, C548S371700

Reexamination Certificate

active

06265430

ABSTRACT:

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-[(trifluoro-methyl)-sulphinyl]-1H-pyrazole, exhibit a good activity against pests (cf. for example EP-A 295 117 and EP-A 352 944).
Also described are a large number of substituted 1-arylpyrazoles which can be employed for controlling pests (cf., for example, EP-A 201 852, EP-A 418 016 or EP-A 0 659 745).
However, the level of action or duration of action of the prior-art compounds is not entirely satisfactory in all fields of application, in particular in the case of specific insects or when low concentrations are applied.
There have now been found new 3-thiocarbamoylpyrazole derivatives of the general formula (I)
in which
R
1
represents H
2
N—CS—,
R
2
represents halogenoalkyl, halogenoalkenyl or halogenoalkinyl,
R
3
represents hydrogen, amino or one of the following groups:
 where
R
4
represents alkyl, halogenoalkyl, alkoxyalkyl or in each case optionally substituted phenyl or pyridyl,
R
5
represents hydrogen or alkyl,
R
6
represents hydrogen, alkyl or in each case optionally substituted phenyl or pyridyl and
R
7
represents alkyl, alkenyl, alkinyl, formyl, alkylcarbonyl, halogenoalkylcarbonyl or alkoxycarbonyl;
Ar represents in each case optionally substituted phenyl or pyridyl and
n represents a number 0, 1 or 2.
It has furthermore been found that the new 3-thiocarbamoylpyrazole derivatives of the formula (I) are obtained when
a) 3-cyanopyrazole derivatives of the formula (II)
 in which
Ar, R
2
, R
3
and n are as defined above are reacted with hydrogen sulphide, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent; or
b) 3-thiocarbamoylpyrazole derivatives of the formula (III)
 in which
Ar is as defined above and
R
3-1
represents one of the following groups:
 where
R
4
, R
5
, R
6
and R
7
are as defined above are reacted with sulphenyl halides of the formula (IV)
Hal—S—R
2
  (IV)
 in which
R
2
is as defined above 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; or
c) the 2-thiocarbamoylpyrazole derivatives of the formula (Ia)
 in which
Ar, R
2
and R
3
are as defined above and which can be obtained by process (a) or (b) are oxidized with oxidants, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Finally, it has been found that the new 3-thiocarbamoylpyrazole derivatives of the formula (I) have highly pronounced biological properties and are suitable, above all, for controlling animal pests, in particular insects, arachnids and nematodes which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals given in the formulae hereinabove and hereinbelow are illustrated in the following text.
R
1
represents H
2
N—CS—.
R
2
preferably represents (C
1
-C
6
)-halogenoalkyl having 1 to 12 halogen atoms; (C
2
-C
6
)-halogenoalkenyl having 1 to 8 halogen atoms or (C
2
-C
6
)-halogenoalkinyl having 1 to 6 halogen atoms.
R
3
preferably represents hydrogen, amino or one of the following groups:
 where
R
4
represents (C
1
-C
6
)-alkyl, (C
1
-C
6
)-halogenoalkyl having 1 to 3 halogen atoms, (C
1
-C
6
)-alkoxy-(C
1
-C
6
)-alkyl, or represents phenyl or pyridyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy or C
1
-C
4
-halogenoalkylthio having in each case 1 to 5 halogen atoms,
R
5
represents hydrogen or (C
1
-C
6
)-alkyl,
R
6
represents hydrogen, (C
1
-C
6
)-alkyl, phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy or C
1
-C
4
-halogenoalkylthio having in each case 1 to 5 halogen atoms or hydroxyl, or represents pyridyl which is substituted by cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy or C
1
-C
4
-halogenoalkylthio having in each case 1 to 5 halogen atoms, and
R
7
represents (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkinyl, formyl, (C
1
-C
6
)-alkylcarbonyl, (C
1
-C
6
)-halogenoalkylcarbonyl having 1 to 6 halogen atoms or (C
1
-C
6
)-alkoxycarbonyl.
Ar preferably represents phenyl or pyridyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen halogeno(C
1
-C
6
)alkyl, halogeno(C
1
-C
6
)alkylthio, halogeno(C
1
-C
6
)alkoxy, (C
1
-C
6
)alkoxy, methoxy, hydrazino, (C
1
-C
6
)-dialkylhydrazino, amino, (C
1
-C
6
)alkylamino, di(C
1
-C
6
)alkylamino, (C
1
-C
6
)alkylimino, cyano, (C
1
-C
6
)alkylthio or the group
 in which
R
8
and R
9
are identical or different and represent hydrogen or (C
1
-C
6
)-alkyl
n preferably represents a number 0, 1 or 2.
R
1
represents H
2
N—CS—.
R
2
particularly preferably represents (C
1
-C
4
)-halogenoalkyl having 1 or 9 identical or different halogen atoms from the series consisting of fluorine, chlorine and bromine, (C
2
-C
4
)-halogenoalkenyl having 1 to 5 identical or different halogen atoms from the series consisting of fluorine, chlorine or bromine or (C
2
-C
4
)-halogenoalkinyl having 1 to 5 identical or different halogen atoms from the series consisting of fluorine, chlorine and bromine.
R
3
especially preferably represents hydrogen, amino or one of the following groups:
 where
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 from the series consisting of hydroxyl, cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
2
-halogenoalkyl, C
1
-C
2
-halogenoalkoxy or C
1
-C
2
-halogenoalkylthio having in each case 1 to 3 halogen atoms,
R
5
represents hydrogen or (C
1
-C
4
)-alkyl,
R
6
represents hydrogen, (C
1
-C
4
)-alkyl or, or phenyl which is optionally monosubstituted or disubstituted by identical or different substitutents from the series consisting of hydroxyl, cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
2
-halogenoalkyl, C
1
-C
2
-halogenoalkoxy or C
1
-C
2
-halogenoalkylthio having in each case 1 to 3 halogen atoms, in particular 4-hydroxy-3-methoxy-phenyl, and
R
7
represents (C
1
-C
4
)-alkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-alkinyl, formyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-halogenoalkylcarbonyl having 1 to 5 identical or different halogen atoms from the series consisting of fluorine, chlorine or bromine or (C
1
-C
4
)-alkoxycarbonyl.
Ar especially preferably represents phenyl or pyridyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of fluorine, chlorine, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, iminomethyl, cyano, methylthio or the group
 where
R
8
and R
9
are identical or different and represent hydrogen or (C
1
-C
4
)-alkyl.
n especially preferably represents a number 0, 1 or 2.
R
1
represents H
2
N—CS—.
R
2
most preferably represents one of the radicals:
—CF
3
, —CHF
2
—CF
2
—CH
3
, —CF
3
—CHF
2
, —CF
2
—CHFCl,
—CH
2
—CF
3
, —CH
2
—CF
2
Cl,
—CH
2
—CF
2
—CHF
2
,
—CF
2
—CFCl—CF
3
,
—C(Cl)(CF
3
)—CF
2
Cl, —C(Cl)(CF
3
)—CHCl—CF
3
,
—C(CF3)═CCl
2
R
3
most preferably represents hydrogen, amino or one of

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