Disubstituted biphenyloxazolines

Details Disubstituted biphenyloxazolines Disubstituted biphenyloxazolines

1999-08-23

2002-06-25

Morris, Patricia L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C548S239000

Reexamination Certificate

active

06410581

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to novel biphenyloxazolines, to processes for their preparation and to the use of the biphenyloxazolines for controlling animal pests.
BACKGROUND OF THE INVENTION
It is known that certain biphenyloxazolines have insecticidal and acaricidal activity, for example the compounds 2-(2,6-difluorophenyl)-4-(3′-chloro-4′-(1,1,2,2-tetrafluoroethoxy)-biphenyl-4)-2-oxazoline (EP-A-0 696 584) and 2-(2,6-difluorophenyl)-4-(3′-chloro-4′-methylbiphenyl-4)-2-oxazoline (EP-A-0 432 661).
However, the efficacy and/or the duration of action of these known compounds, in particular against certain organisms or at low application concentrations, is not entirely satisfactory in all areas of use.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel disubstituted biphenyloxazolines of the formula (I)
in which
X
1
represents hydrogen, halogen, alkyl, alkoxy or alkylthio,
X
2
represents halogen, alkyl, alkoxy or alkylthio,
X
3
represents hydrogen, halogen, alkyl, alkoxy or alkylthio, in particular hydrogen,
R
1
represents hydrogen, halogen, alkyl or —CH
2
—CR
4
═CH
2
,
R
2
represents alkyl, hydroxyalkyl, respectively optionally substituted alkenyl, alkinyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, phenyl-alkyl, naphthylalkyl or tetrahydronaphthylalkyl and
R
3
represents hydrogen, alkyl, halogen or the radical —CH
2
—CR
4
═CH
2
, where R
1
and R
3
do not simultaneously represent hydrogen, and
R
4
represents hydrogen or respectively optionally substituted alkyl or aryl.
Owing to one or more chiral centres, the compounds of the formula (I) are generally obtained as stereoisomer mixtures. They can be employed both in the form of their diastereomer mixtures and as pure diastereomers or enantiomers.
Furthermore, it has been found that the novel compounds of the formula (I) are obtained when
A) compounds of the formula (II)
 in which
X
1
, X
2
, X
3
, R
3
and R
1
are each as defined above, R
3
═R
1
=hydrogen being possible here if R
2
represents allyl and step B) is carried out,
 are reacted with compounds of the formula (III)
Z—R
2
  (III),
 in which
R
2
is as defined above and
Z represents a leaving group,
 if appropriate in the presence of a diluent and if appropriate in the presence of a base and
B) if appropriate, the compounds of the formula (IV) obtained in this manner for R
2
═—CH
2
—CR
4
═CH
2
and R
3
═H
 in which
R
1
, R
4
, X
1
, X
2
and X
3
are each as defined above,
 are subsequently subjected to a Claisen rearrangement and
C) if appropriate, the resulting compounds of the formula (V)
 in which
X
1
, X
2
, X
3
, R
1
and R
4
are each as defined above,
 are subsequently reacted with compounds of the formula (III)
Z—R
2
  (III),
 in which
R
2
and Z are each as defined above,
 if appropriate in the presence of a diluent and if appropriate in the presence of a base and,
if appropriate, steps B) and C) are then repeated for R
2
═—CH
2
—CR
4
═CH
2
and R
1
═H, affording compounds of formula (Va)
 in which
X
1
, X
2
, X
3
, R
2
and R
4
are each as defined above,
and the radicals R
4
may be identical or different.
Furthermore, it has been found that the novel compounds of the formula (I) are highly suitable for controlling animal pests, in particular insects, arachnids and nematodes which are encountered in agriculture, in forests, in the protection of materials and of stored goods and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated below.
X
1
preferably represents hydrogen, fluorine, chlorine, bromine, iodine, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkylthio.
X
2
preferably represents fluorine, chlorine, bromine, iodine, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkylthio.
X
3
preferably represents hydrogen, fluorine, chlorine, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy, in particular hydrogen.
R
1
preferably represents hydrogen, fluorine, chlorine, bromine, C
1
-C
6
-alkyl or —CH
2
—CR
4
═CH
2
.
R
2
preferably represents C
1
-C
8
-alkyl, C
1
-C
6
-hydroxyalkyl, C
3
-C
10
-alkenyl, C
3
-C
12
-alkinyl, preferably represents respectively optionally halogen- or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl or C
4
-C
6
-cycloalkenyl,
preferably represents optionally halogen-, C
1
-C
4
-alkyl-, C
2
-C
4
-alkenyl-, C
2
-C
4
-halogenoalkenyl-, phenyl-, halogenophenyl-, styryl- or halogenostyryl-substituted C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl,
preferably represents optionally halogen- or C
1
-C
4
-alkyl-substituted C
4
-C
8
-cycloalkenyl-C
1
-C
2
-alkyl,
or preferably represents phenyl-C
1
-C
4
-alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of nitro, halogen, C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl, C
1
-C
12
-alkylthio, C
1
-C
12
-halogenoalkylthio, C
1
-C
12
-alkoxy and C
1
-C
12
-halogenoalkoxy, preferably represents naphthyl-C
1
-C
3
-alkyl or tetrahydronaphthyl-C
1
-C
3
-alkyl.
R
3
preferably represents hydrogen, C
1
-C
4
-alkyl, fluorine, chlorine, bromine or represents —CH
2
—CR
4
═CH
2
, where R
1
and R
3
do not simultaneously represent hydrogen.
R
4
preferably represents hydrogen, C
1
-C
12
-alkyl or preferably represents phenyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
12
-alkyl, C
1
-C
12
-halogenoalkyl, C
1
-C
12
-alkoxy and C
1
-C
12
-halogenoalkoxy.
X
1
particularly preferably represents hydrogen, fluorine or chlorine.
X
2
particularly preferably represents fluorine, chlorine, bromine, iodine, C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy.
X
3
particularly preferably represents hydrogen, fluorine, chlorine, C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy, in particular hydrogen.
R
1
particularly preferably represents hydrogen, fluorine, chlorine, bromine, C
1
-C
4
-alkyl or —CH
2
—CR
4
═CH
2
.
R
2
particularly preferably represents C
1
-C
6
-alkyl, C
1
-C
4
-hydroxyalkyl, C
3
-C
10
-alkenyl, C
3
-C
5
-alkinyl, particularly preferably represents respectively optionally halogen- or C
1
-C
4
-alkyl-substituted cyclohexyl or C
4
-C
6
-cycloalkenyl,
particularly preferably represents optionally halogen-, C
1
C
4
-alkyl-, C
2
-C
4
-alkenyl-, C
2
-C
3
-halogenoalkenyl-, phenyl-, halogenophenyl-, styryl- or halogenostyryl-substituted C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl,
particularly preferably represents optionally halogen-substituted C
4
-C
6
-cycloalkenylmethyl or
particularly preferably represents benzyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkylthio,
C
1
-C
4
-halogenoalkylthio, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkoxy, particularly preferably represents naphthylmethyl or tetrahydronaphthyl-methyl.
R
3
particularly preferably represents hydrogen, C
1
-C
3
-alkyl, chlorine, bromine or —CH
2
—CR
4
═CH
2
, where R
1
and R
3
do not simultaneously represent hydrogen.
R
4
particularly preferably represents hydrogen, C
1
-C
4
-alkyl or particularly preferably represents phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy.
In the preferred and particularly preferred radical definitions, halogen represents in particular fluorine, chlorine and bromine.
X
1
very particularly preferably represents hydrogen, fluorine or chlorine.
X
2
very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl or methoxy.
X
3
very particularly preferably represents hydrogen, fluorine, chlorine or methyl, in particular hydrogen.
R
1
very particularly

Affiliated with

Also associated with

Rating

Disubstituted biphenyloxazolines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Disubstituted biphenyloxazolines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Disubstituted biphenyloxazolines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2905025