Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1996-07-11
2001-09-18
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S131000
Reexamination Certificate
active
06291492
ABSTRACT:
The invention relates to new 3-aryl-alkenyl-1,2,4-oxadiazole derivatives, to a plurality of processes for their preparation, and to their use for combating animal pests.
The preparation of a variety of 3,5-disubstituted 1,2,4-oxadiazoles such as, for example, 5-(2,4-dichlorophenyl)-3-[2-(2,4-dichlorophenyl)-ethenyl]-1,2,4-oxadiazole, has already been described (cf. J. Heterocycl. Chem., 15 (8), 1373-8, 1978).
Equally, it is already known that certain 1,2,4-oxadiazole derivatives have a parasiticidal (in particular endoparaciticidal) activity in humans and animals (cf. U.S. Pat. No. 4,012,377 and German Offenlegungschrift 40 41 474).
Furthermore, it is known that certain 1,2,4-oxadiazole derivatives can be used as insecticides and acaricides (cf. DE 41 24 151).
However, the activity of these prior-art compounds is not always entirely satisfactory in all fields of application, in particular when low amounts and concentrations are applied.
There have now been found new 3-aryl-alkenyl-1,2,4-oxadiazole derivatives of the formula (I)
in which
R
1
represents halogen, alkyl or alkoxy,
R
2
represents hydrogen, halogen, halogenoalkyl or halogenoalkoxy,
R
3
represents hydrogen or alkyl,
R
4
represents halogen, trialkylsilylalkyl, trialkylsilylalkoxy; or a group —A
k
—R
7
, in which
A represents oxygen, sulfur, SO, SO
2
, alkylene, alkyleneoxy, alkylenethio, oxyalkylene, oxyalkyleneoxy, alkyleneoxyalkylene, alkenediyl or alkinediyl,
k represents a number 0 or 1,
R
7
represents alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl or halogenoalkinyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted pyridyl, or
R
4
represents optionally substituted cycloalkyl, where, if appropriate, one or two CH
2
groups which are not linked directly to each other are replaced by oxygen and/or sulfur,
R
5
and R
6
represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy,
m represents a number 1, 2 or 3,
n represents a number 1 or 2,
Y represents a nitrogen atom or the group C—R
9
in which
R
9
represents hydrogen, halogen or alkyl;
with the exception of the compounds:
5- (2,4-dichlorophenyl) -3-[2-(2,4-dichlorophenyl)-ethenyl]-1,2,4-oxadiazole (cf. J. Heterorcycl. Chem. 15 (8), 1373—8, 1978) and 5-(2,6-difluorophenyl)-3-[2-(2,3,4-trimethoxyphenoxy)ethenyl]-1,2,4-oxadiazole (cf. WO 93/01719).
Depending on the nature of the substituents, the compounds of the formula (I) can exist as geometric and/or optical isomers, or variously composed mixtures of isomers. The invention relates to the pure isomers and to the mixtures of isomers.
Furthermore, it has been found that the new 3-aryl-alkenyl-1,2,4-oxadiazole derivatives of the formula (I) are obtained by
a) reacting an amide oxime derivative of the formula (II) and stereoisomers thereof
in which
R
3
, R
4
, R
5
, R
6
and n have the abovementioned meanings
with carboxylic acid derivatives of the formulae (III), (IV) or (V)
in which
R
1
,R
2
, Y and m have the abovementioned meanings,
R represents alkyl, in particular methyl or ethyl, and
Hal represents halogen, such as fluorine, chlorine or bromine, preferably chlorine,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or
b) cyclizing compounds of the formula (VI)
in which
Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, m and n have the above-mentioned meanings,
in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or
c) reacting phosphonium halides of the formula (VII)
in which
R
1
, R
2
, Y and m have the abovementioned meanings and
Ph represents phenyl and
Hal represents chlorine, bromine or iodine, in particular chlorine and bromine, or
phosphonic esters of the formula (VIIa)
in which
R
1
, R
2
, Y and m have the abovementioned meanings and
R represents alkyl, in particular methyl or ethyl,
with aldehydes or ketones of the formula (VIII)
in which
R
3
, R
4
, R
5
, R
6
and n have the abovementioned meanings,
in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
Furthermore, it has been found that the new 3-aryl-alkenyl-1,2,4-oxadiazole derivatives of the formula (I) are highly suitable for combating animal pests. They are distinguished, in particular, by a powerful activity against arthropods and nematodes.
Surprisingly, the 3-aryl-alkenyl-1,2,4-oxadiazole derivatives of the formula (I) according to the invention display a considerably better activity against animal pests than the prior-art compounds having the most similar constitution.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents, or ranges of the radicals whose formulae are given hereinabove and hereinbelow will be illustrated in the following text.
R
1
preferably represents fluorine, chlorine, bromine, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy.
R
2
preferably represents hydrogen, fluorine, chlorine, bromine, C
1
-C
6
-halogenoalkyl or C
1
-C
6
-halogenoalkoxy.
R
3
preferably represents hydrogen or C
1
-C
4
-alkyl.
R
4
preferably represents fluorine, chlorine, bromine, tri-(C
1
-C
8
-)-alkylsilyl-(C
1
-C
6
-)-alkyl or tri-(C
1
-C
8
)-alkylsilyl-(C
1
-C
6
-)-alkoxy or a group —A
k
—R
7
, in which
A represents oxygen, sulfur, SO, SO
2
, C
1
-C
6
-alkylene, C
1
-C
6
-alkyleneoxy, C
1
-C
6
-alkylenethio, C
1
-C
6
-oxyalkylene, C
1
-C
6
-oxyalkyleneoxy, C
1
-C
6
-alkyleneoxy-C
1
-C
6
-alkylene, C
2
-C
5
-alkenediyl or C
2
-C
5
-alkinediyl,
k represents a number 0 or 1 and
R
7
represents C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl or C
2
-C
20
-alkinyl, each of which is optionally monosubstituted or polysubstituted by fluorine and/or chlorine, or represents C
3
-C
12
-cycloalkyl which is optionally monosubstituted to trisubstituted by identical or different substituents, where, if appropriate, one or two CH
2
groups which are not directly adjacent to each other are replaced by oxygen and/or sulfur, or represents phenyl which is optionally monosubstituted to pentasubstituted by identical or different substituents, or pyridyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable cycloalkyl, phenyl or pyridyl substituents being those mentioned below:
halogen,
C
1
-C
18
-alkyl,
C
1
-C
8
-alkoxy-C
l
-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 1-3 oxygen atoms,
C
1
-C
18
-alkylthio,
C
1
-C
8
-halogenoalkylthio,
3, 4-difluoromethylenedioxo,
3, 4-tetrafluoroethylenedioxo,
benzyliminooxymethyl which is optionally substituted by C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl and/or halogen,
cyclohexyl and cyclohexyloxy, each of which is optionally substituted by C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, cyclohexyl and/or phenyl;
pyridyloxy which is optionally monosubstituted or disubstituted by identical or different substituents from the series consisting of halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl;
phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio, each of which is optionally monosubstituted to disubstituted by identical or different substituents from the series consisting of C
1
-C
12
-alkyl, halogen, C
1
-C
4
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, C
l
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-ethyleneoxy, C
1
-C
6
-alkylthio and/or C
1
-C
6
-halogenoalkylthio.
R
5
and R
6
independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, C
1
-C
8
-alkyl, C
1
-C
8
-halogenoalkyl, C
1
-C
8
-alkoxy or C
1
-C
8
-halogenoalkoxy.
m preferably represents a number 1, 2 or 3.
n preferably represents a number 1 or 2.
Y preferably represents nitrogen or the group —CR
9
, in which
R
9
represents hydrogen, fluorine, chlorine, bromine or C
1
-C
6
-alkyl.
R
1
particularly preferably represents fluorine, chlorine, bromine, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy.
R
2
particularly preferably represents hydrogen, fluorine, chlorine, bromine, C
1
-C
4
-halogenoalkyl or C
1
-C
4
-halogeno
Erdelen Christoph
Jeschke Peter
Mencke Norbert
Turberg Andreas
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Gerstl Robert
Norris & McLaughlin & Marcus
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