Biphenyl ether oxazolines and their use as pest-control agents

Details Biphenyl ether oxazolines and their use as pest-control agents Biphenyl ether oxazolines and their use as pest-control agents

1998-05-12

2001-04-03

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S212010, C514S229200, C514S236800, C514S326000, C514S340000, C514S365000, C540S603000, C544S065000, C544S137000, C546S208000, C546S271400, C548S146000, C548S237000

Reexamination Certificate

active

06211214

ABSTRACT:

This application is the national stage of PCT/EP96/04846, filed Nov. 6, 1996.
The present invention relates to novel biphenyl ether-oxazolines, processes for their preparation and their use for controlling animal pests, and to novel intermediate products.
It is already known that certain substituted biphenyl-oxazolines, such as, for example, 2-(2,6-difluorophenyl)-4-(4′-methoxybiphenyl-4-yl)-1,3-oxazoline, have an insecticidal and acaricidal action (cf. EP-A 0 432 661).
However, the level of action and/or duration of action of these known compounds is not completely satisfactory in all fields of use, especially against certain organisms or if low concentrations are used.
Novel biphenyl ether-oxazolines of the formula (I)
in which
X represents hydrogen, fluorine or chlorine,
Y represents fluorine, chlorine or methyl,
Z represents hydrogen, halogen, alkyl, alkoxy or dialkylamino,
R
1
and R
2
independently of one another represent halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,
m and n independently of one another represent 0, 1 or 2 and
A represents the grouping —(CH
2
)
p
—(CR
3
R
4
)
q
—(CH
2
)
r
—R wherein
R
3
and R
4
independently of one another represent hydrogen or alkyl,
p, q and r independently of one another represent 0, 1, 2 or 3, at least one index being other than 0, and
R represents cyano; or represents an optionally substituted, saturated, partly saturated or unsaturated 5- or 6-membered heterocyclic radical, or represents one of the following groupings:
wherein
R
5
represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted cycloalkyl or optionally substituted aryl,
R
6
represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, optionally substituted arylalkyl or in each case optionally substituted cycloalkyl or cycloalkylalkyl,
R
7
and R
8
independently of one another represent hydrogen, alkyl, alkoxy, alkenyl, halogenoalkyl, halogenoalkenyl, in each case optionally substituted aryl or arylalkyl, or in each case optionally substituted cycloalkyl or cycloalkylalkyl, or represent —OR
6
or —NR
5
R
6
, wherein
R
5
and R
6
have the abovementioned meaning, or
R
7
and R
8
together represent a 5- or 6-membered alkylene chain, which optionally contains an oxygen atom,
R
9
and R
10
independently of one another represent alkyl,
R
11
represents —OR
6
, —NR
5
R
6
or —N(R
5
)—COOR
6
, wherein
R
5
and R
6
have the abovementioned meaning, and
R
12
, R
13
and R
14
independently of one another represent alkyl, have now been found.
The biphenyl ether-oxazolines of the formula (I) can be obtained as optical and/or geometric isomers, also depending on the substituents. The present invention relates both to the isomer mixtures and to the pure isomers.
It has furthermore been found that the biphenyl ether-oxazolines of the formula (I) are obtained by a process in which hydroxybiphenyloxazolines of the formula (II)
in which
X, Y, Z, R
1
, R
2
, m and n have the abovementioned meaning,
are reacted with a compound of the formula (III)
M—A  (III)
in which
A has the abovementioned meaning and
M represents a leaving group,
if appropriate in the presence of a base and/or a catalyst and if appropriate in the presence of a diluent.
It has furthermore been found that the novel substituted biphenyl ether-oxazolines of the formula (I) are particularly suitable for controlling animal pests, in particular insects, arachnids and nematodes which occur in agriculture, in forestry, in the preservation 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 and ranges of the radicals listed in the formulae mentioned above and below are explained in the following.
X preferably represents hydrogen, fluorine or chlorine.
Y preferably represents fluorine, chlorine or methyl.
Z preferably represents hydrogen, fluorine, chlorine, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or di(C
1
-C
4
)alkylamino.
R
1
and R
2
independently of one another preferably represent fluorine, chlorine, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy or C
1
-C
4
-halogenoalkylthio.
m and n independently of one another preferably represent 0, 1 or 2.
A preferably represents the grouping (CH
2
)
p
—(CR
3
R
4
)
q
—(CH
2
)
r
—R, wherein
R
3
and R
4
independently of one another represent hydrogen or C
1
-C
4
-alkyl,
p, q and r independently of one another represent 0, 1, 2 or 3, at least one index being other than 0 and the sum of the indices being not greater than 5.
R Preferably represents cyano; or represents a saturated, partly saturated or unsaturated 5- or 6-membered heterocyclic radical which has 1 to 3 identical or different heteroatoms from the series consisting of nitrogen, oxygen and sulfur and is optionally substituted by halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl, or represents one of the following groupings:
wherein
R
5
represents hydrogen, C
1
-C
6
-alkyl, C
1
-C
4
-halogenoalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-halogenoalkyl; or C
3
-C
6
-cycloalkyl which is optionally substituted once or several times in an identical or different manner by C
1
-C
4
-alkyl, halogen or C
1
-C
4
-halogenoalkyl, or represents phenyl which is optionally substituted once to five times in an identical or different manner by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio, di(C
1
-C
4
)alkylamino, C
1
-C
4
-alkylcarbonyl-amino, C
1
-C
4
-alkylcarbonyl-C
1
-C
4
-alkyl amino, cyano, nitro, —COOR
15
or —CONR
16
R
17
,
R
6
represents hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-halogenoalkenyl; or C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, in each case optionally substituted once or several times in an identical or different manner by C
1
-C
4
-alkyl, halogen or C
1
-C
4
-halogenoalkyl,
 or represents C
6
-C
10
-aryl-C
1
-C
6
-alkyl which is optionally substituted once to five times in an identical or different manner by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio, di(C
1
-C
4
)alkylamino, cyano, nitro, —COOR
15
or —CONR
16
R
17
,
R
7
and R
8
independently of one another represent hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-halogenoalkenyl; or C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, in each case optionally substituted once or several times in an identical or different manner by C
1
-C
4
-alkyl, halogen or C
1
-C
4
-halogenoalkyl,
 or represent phenyl or phenyl-C
1
-C
4
-alkyl, in each case optionally substituted once to five times in an identical or different manner by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio, di(C
1
-C
4
)alkylamino, cyano, nitro, —COOR
15
or —CONR
16
R
17
, or represent —OR
6
or —NR
5
R
6
, or
R
7
and R
8
together represent —(CH
2
)
5
—, —(CH
2
)
6
— or —(CH
2
)
2
—O—(CH
2
)
2
—;
R
9
and R
10
independently of one another represent C
1
-C
4
-alkyl;
R
11
represents —OR
6
—, —NR
5
R
6
or —N(R
5
)—COOR
6
, and
R
12
, R
13
and R
14
independently of one another represent C
1
-C
4
-alkyl.
R
15
preferably represents hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl; or C
3
-C
6
-cycloalkyl which is optionally substituted once or several times in an identical or different manner by C
1
-C
4
-alkyl, halogen or C
1
-C
4
-halogenoalkyl,
 or represents phenyl which is optionally substituted once to five times in an identical or different manner by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio, di(C
1
-C
4
)alkylamino, cyano, nitro, C
1
-C
6
-alkoxycarbonyl or di(C
1
-C
6
)alkylaminocarbonyl.
R
1

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