Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-06-19
2001-07-03
Gerstl, Robert (Department: 1613)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S146000
Reexamination Certificate
active
06255328
ABSTRACT:
The invention relates to novel substituted thiazolines, processes for their preparation, and to their use for controlling animal pests.
It is already known that certain oxazoline derivatives have insecticidal and acaricidal properties (cf. for example EP-A-0 345 775 or EP-A-0 432 661).
However, the potency and/or persistency of these prior-art compounds is not entirely satisfactory in all fields of application, in particular when used against certain organisms or at low application rates.
The invention provides novel substituted thiazolines of the formula (I)
in which
Ar
1
and Ar
2
each represent independently of one another optionally substituted phenyl.
The invention further provides a process for preparing the novel substituted thiazolines of the formula (I) by reacting
a) oxazolines of the formula (II)
in which
Ar
1
and Ar
2
each have the abovementioned meaning with a sulphurizing agent, optionally in the presence of a diluent;
or by reacting
b) thiazolines of the formula (Ia)
in which
Ar
1
has the abovementioned meaning and
Ph represents optionally substituted halogenophenyl
with boronic acids of the formula (III)
Ph
1
—B(OH)
2
(III)
in which
Ph
1
represents optionally substituted phenyl
in the presence of a base, optionally in the presence of a catalyst and in the presence of a diluent.
Furthermore, it has been found that the novel substituted thiazolines of the formula (I) are highly suitable for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field.
Surprisingly, the substituted thiazolines of the formula (I) according to the invention have a considerably higher activity against animal pests than the prior-art compounds of a similar structure.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals mentioned in the formulae given hereinabove and hereinbelow are illustrated below.
Ar
1
preferably represents phenyl which is optionally substituted by one to five identical or different substituents from the group consisting of:
halogen, nitro, cyano, hydroxyl, amino,
C
1
-C
6
-alkyl,
C
1
-C
6
-alkoxy,
C
1
-C
6
-alkylthio,
C
1
-C
6
-alkylsulphinyl,
C
1
-C
6
-alkylsulphonyl,
C
1
-C
6
-halogenoalkyl,
C
1
-C
6
-halogenoalkoxy,
C
1
-C
6
-halogenoalkylthio,
C
1
-C
6
-halogenoalkylsulphinyl,
C
1
-C
6
-halogenoalkylsulphonyl,
C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
C
1
-C
6
-alkylamino,
di-(C
1
-C
6
-alkyl)-amino,
and phenyl, benzyl, benzyloxy, phenethyl, phenethenyl, phenethinyl, phenoxy or phenylthio, each of which is optionally substituted in particular in the phenyl moiety by one to five identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-alkylthio or C
1
-C
4
-halogenoalkylthio.
Ar
2
preferably represents phenyl which is optionally substituted by one to five identical or different substituents from the group consisting of:
halogen,
C
1
-C
18
-alkyl,
C
1
-C
8
-alkoxy-C
1
-C
8
-alkyl,
C
1
-C
8
-halogenoalkoxy,
C
1
-C
4
-halogenoalkyl,
C
1
-C
18
-alkoxy which is optionally interrupted by a further 1 to 3 oxygen atoms,
C
1
-C
18
-alkylthio,
C
1
-C
8
-halogenoalkylthio,
tri-C
1
-C
8
-alkylsilyl,
phenyl-di-C
1
-C
8
-alkylsilyl,
3,4-difluoromethylenedioxo,
3,4-tetrafluoroethylenedioxo,
a benzo-fused group,
a fused C
4
-alkanediyl group,
benzyliminooxymethyl which is optionally substituted by C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl or halogen,
cyclohexyl or cyclohexyloxy, each of which is optionally substituted by C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, cyclohexyl or phenyl,
pyridyloxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl,
and phenyl, phenyl-C
1
-C
6
-alkyl, phenethenyl, phenethinyl, phenoxy, phenylthio, phenyl-C
1
-C
6
-alkyloxy or benzylthio, each of which is optionally substituted in particular in the phenyl moiety by one to three identical or different R
1
and/or optionally substituted in particular in the phenyl moiety by one or two identical or different —OR
2
.
R
1
preferably represents halogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy.
R
2
preferably represents hydrogen, or C
1
-C
12
-alkyl, C
3
-C
12
-alkenyl, or C
3
-C
12
-alkinyl, or C
1
-C
6
-halogenoalkyl having one or more fluorine and/or chlorine atoms, or C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, each of which is optionally mono- or polysubstituted in the cycloalkyl moiety by identical or different substituents from the group consisting of:
halogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl which is optionally mono- or polysubstituted by halogen, and phenyl or styryl, each of which is optionally mono- or polysubstituted, in particular in the phenyl moiety, by halogen;
or represents C
4
-C
6
-cycloalkenyl or C
4
-C
6
-cycloalkenyl-C
1
-C
4
-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen and/or C
1
-C
4
-alkyl substituents;
or represents phenyl-C
1
-C
4
-alkyl or naphthylmethyl, each of which is optionally mono- or polysubstituted in the aryl moiety by identical or different substituents from the group consisting of:
halogen, C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl having one or more fluorine and/or chlorine atoms, C
1
-C
12
-alkoxy and C
1
-C
12
-halogenoalkoxy having one or more fluorine and/or chlorine atoms;
or represents the radical —COR
3
.
R
3
preferably represents C
1
-C
12
-alkyl, or C
1
-C
12
-alkoxy, or C
3
-C
12
-alkenyl, or C
3
-C
12
-alkenyloxy, or represents C
3
-C
6
-cycloalkyl, C
3
-C
10
-cycloalkyloxy or C
3
-C
10
-cycloalkyl-C
1
-C
6
-alkoxy, each of which is optionally mono- or polysubstituted in the cycloalkyl moiety by identical or different substituents from the group consisting of:
C
1
-C
4
-alkyl, halogen, C
1
-C
4
-halogenoalkyl having one or more fluorine and/or chlorine atoms and C
2
-C
4
-halogenoalkenyl having one or more fluorine and/or chlorine atoms;
or represents phenyl or naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of:
halogen, C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl having one or more fluorine and/or chlorine atoms, C
1
-C
12
-alkoxy and C
1
-C
12
-halogenoalkoxy having one or more fluorine and/or chlorine atoms;
or represents the radical —NR—R
5
.
R
4
preferably represents hydrogen or C
1
-C
12
-alkyl.
R
5
preferably represents C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl having one or more fluorine and/or chlorine atoms, or C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, each of which is optionally mono- or polysubstituted in the cycloalkyl moiety by identical or different substituents from the group consisting of:
C
1
-C
4
-alkyl, halogen, C
1
-C
4
-halogenoalkyl having one or more fluorine and/or chlorine atoms and C
2
-C
4
-halogenoalkenyl having one or more fluorine and/or chlorine atoms;
or represents phenyl or phenyl-C
1
-C
6
-alkyl, each of which is optionally mono- or polysubstituted, in particular in the phenyl moiety, by identical or different substituents from the group consisting of:
halogen, C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl having one or more fluorine and/or chlorine atoms, C
1
-C
12
-alkoxy and C
1
-C
12
-halogenoalkoxy having one or more fluorine and/or chlorine atoms;
or represents the radical —C(R
6
R
7
)—C(R
8
)═NOR
9
.
R
6
and R
7
are identical or different and preferably represent hydrogen or C
1
-C
4
-alkyl.
R
8
preferably represents hydrogen, C
1
-C
4
-alkyl or C
3
-C
6
-cycloalkyl which is optionally mono-, di- or trisubstituted by identical or different substituents from the group consisting of C
1
-C
4
-alkyl, halogen or C
1
-C
4
-halogenoalkyl.
R
9
preferably represents C
1
-C
4
-alkyl.
Ar
1
particularly preferably represents phenyl which is optionally substituted by one to five, in particular one to three, i
Alig Bernd
Erdelen Christoph
Kraatz Udo
Kramer Wolfgang
Lantzsch Reinhard
Bayer Aktiengesellschaft
Gerstl Robert
Norris McLaughlin & Marcus P.A.
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