Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1995-08-04
2001-01-09
Shah, Mukund J. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S237000, C548S239000
Reexamination Certificate
active
06172093
ABSTRACT:
The invention relates to new substituted biphenyloxazolines, to a plurality of processes for their preparation, to new intermediates, and to the use of the substituted biphenyloxazolines for combating animal pests.
It is known that certain substituted biphenyloxazolines, such as 2-(2,6-difluorophenyl)-4-(4′-chlorobiphenyl-4)-2-oxazoline, have an insecticidal and acaricidal activity (cf. EP-A-0 432 661).
However, the level and/or duration of activity of these known compounds are not entirely satisfactory in all fields of application, in particular against certain organisms or when low concentrations are applied.
New substituted biphenyloxazolines of the formula (I)
have been found,
in which
A represents hydrogen, fluoro or chloro,
B represents fluoro or chloro,
in which
R represents R
1
or R
2
, where
R
1
represents halogenoalkyl or halogenocycloalkyl having in each case at least one fluorine atom and additionally at least one hydrogen or chlorine atom, or represents halogenocycloalkenyl having at least one fluorine atom,
R
2
represents hydrogen, alkenyl, alkinyl or represents optionally substituted cycloalkyl, or represents optionally substituted cycloalkylalkyl, or represents optionally substituted cycloalkenylalkyl, or represents optionally substituted cycloalkenyl, or represents phenylalkyl or naphthylalkyl, each of which is optionally substituted, represents optionally substituted heteroarylalkyl, or represents the radical COR
3
,
in which
R
3
represents alkyl, alkoxy, alkenyl, alkenyloxy, or represents cycloalkyl, cycloalkyloxy or cycloalkylalkyloxy, or cycloalkylalkyloxy, each of which is optionally substituted, or represents phenyl or naphthyl, each of which is optionally substituted, or represents the radical NR
4
R
5
,
in which
R
4
represents hydrogen or alkyl and
R
5
represents alkyl, halogenoalkyl, or represents cycloalkyl or cycloalkylalkyl, each of which is optionally substituted, or represents phenyl or phenylalkyl, each of which is optionally substituted,
X represents halogen, alkyl or alkoxy,
m represents 0, 1 or 2 and
n represents 1 or 2.
Due to one or more chiral centers, the compounds of the formula (I) are generally obtained in the form of stereoisomer mixtures. They can be used in the form of their diastereomer mixtures and also as pure diastereomers or enantiomers.
Furthermore, it has been found that the new substituted biphenyloxazolines of the formula (I) are obtained by a process wherein
A) in a first step, to obtain compounds of the formula (II)
in which
R
1
, X, m and n have the abovementioned meanings,
&agr;) to obtain compounds of the formula (IIa)
in which
W and Y independently of one another represent fluorine, chlorine or trifluoromethy,
D represents hydrogen or fluorine,
Z represents fluorine or
W and Z together represent -(CF
2
)
1
in which
1 represents 2, 3, or 4,
n represents 1 or 2 and
m represents 0, 1 or 2,
a hydroxybiphenyl of the formula (III)
in which
X, m and n have the abovementioned meanings,
is reacted with a compound of the formula (IV)
in which
W, Y and Z have the abovementioned meanings,
if appropriate in the presence of a base, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent and, if appropriate, the product is subsequently hydrogenated,
or
&bgr;) to obtain compounds of the formula (IIb)
in which
X, m and n have the abovementioned meanings,
hydroxybiphenyls of the abovementioned formula (III) are reacted with a difluorohalogenomethane of the formula (V)
CHF
2
Hal (V)
in which
Hal represents chlorine or bromine,
if appropriate in the presence of a base, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent,
or
&ggr;) to obtain compounds of the formula (IIc)
in which
X, R
1
, m and n have the abovementioned meanings,
aminophenol derivatives of the formula (VI)
in which
X, R
1
, m and n have the abovementioned meanings,
are diazotized and the resulting diazonium salt is reacted with benzene in the presence of acid and iron powder or in the presence of a base and in each case, if appropriate, in the presence of a diluent,
or
&dgr;) to obtain compounds of the formula (IId)
in which
X, m and n have the abovementioned meanings,
a hydroxybiphenyl of the abovementioned formula (III) is reacted with carbon tetrachloride in the presence of hydrofluoric acid, if appropriate in the presence of a diluent,
B) in a second step, to obtain compounds of the formula (VII)
in which
X, R
1
, m and n have the abovementioned meanings,
&agr;) the compounds of the formula (II) which can be obtained by process A) are reacted with acetyl chloride in the presence of an acid or Lewis acid and in the presence of a diluent,
or
&bgr;) to obtain compounds of the formula (VIIa)
in which
B, X, m, n, W, Y and Z have the abovementioned meanings,
a hydroxybiphenyl derivative of the formula (IIIa)
in which
X, m and n have the abovementioned meanings,
is reacted with a compound of the formula (IV)
in which
W, Y and Z have the abovementioned meanings,
if appropriate in the presence of a base, if appropriate in the presence of a catalyst and if appropriate in the presence of a solvent and, if appropriate, the product is subsequently hydrogenated,
or
&ggr;) to obtain compounds of the formula (VIIb)
in which
X, m and n have the abovementioned meanings,
a hydroxybiphenyl derivative of the formula (IIIa) shown above is reacted with a difluorohalogenomethane of the formula (V) shown above, if appropriate in the presence of a base, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent,
C) in a third step, to obtain compounds of the formula (VIII)
in which
X, R
1
, m and n have the abovementioned meanings and
Hal represents chlorine or bromine,
&agr;) the compounds of the formula (VII) shown above, which can be obtained by process B), are chlorinated or brominated, if appropriate in the presence of a diluent,
or
&bgr;) the compounds of the formula (II) shown above, which can be obtained by process A), are reacted with halogenoacetyl chlorides of the formula (IX)
HalCH
2
COCl (IX)
in which
Hal represents chlorine or bromine,
in the presence of an acid or Lewis acid and in the presence of a diluent,
D) in a fourth step, to obtain compounds of the formula (X)
in which
X, R
1
, m and n have the abovementioned meanings,
the compounds of the formula (VIII) shown above, which can be obtained by process C), are reacted with a salt of formic acid, in the presence of a diluent and if appropriate in the presence of a catalyst,
E) in a fifth step, to obtain compounds of the formula (XI)
in which
X, R
1
, m and n have the abovementioned meanings,
the compounds of the formula (X) shown above, which can be obtained by process D), are reacted with the compound of the formula (XII)
H
2
N—OCH
3
(XII),
if appropriate in the presence of a diluent,
F) in a sixth step, to obtain compounds of the formula (XIII)
in which
R
1
, X, m and n have the abovementioned meanings,
the compounds of the formula (XI) shown above, which can be obtained by process E), are reduced using a reducing agent in the presence of an acid and if appropriate in the presence of a diluent,
G) in a seventh step, to obtain compounds of the formula (XIV)
in which
A, B, R
1
, X, m, and n have the abovementioned meanings, either
&agr;) the compounds of the formula (XIII) shown above, which can be obtained by process F), are reacted with 2-A, 6-B- benzoyl chloride if appropriate in the presence of a base and if appropriate in the presence of a dituent,
or
&bgr;) the compounds of the formula (II) shown above, which can be obtained by process A), are first reacted with a compound of the formula (XV)
in which
A and B have the abovementioned meanings,
V represents chlorine, hydroxyl or C
1
-C
4
-alkoxy and
R
6
represents hydrogen or alkyl, preferably hydrogen or C
1
-C
6
-alkyl,
in the presence of an acidic catalyst and if appropriate in
Erdelen Christoph
Kr{umlaut over (a)}mer Wolfgang
Lantzsch Reinhard
Marhold Albrecht
Mencke Norbert
Bayer Aktiengesellschaft
Coleman Brenda
Norris McLaughlin & Marcus P.A.
Shah Mukund J.
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