4-trifluoromethyl-3-oxazolylpyridines, processes for their...

Details 4-trifluoromethyl-3-oxazolylpyridines, processes for their... 4-trifluoromethyl-3-oxazolylpyridines, processes for their...

1999-12-15

2003-04-29

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S271400

Reexamination Certificate

active

06555501

ABSTRACT:

The invention relates to 4-trifluoromethyl-3-oxazolylpyridines, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.
It is already known that suitably substituted pyridines have acaricidal and insecticidal action. Thus, WO 95/07891 discloses pyridines which carry, in the 4 position, a cycloalkyl radical which is attached via a heteroatom and, in the 3 position, a group of various substituents. However, the desired action with respect to harmful organisms is not always satisfactory. Additionally, these compounds frequently have undesirable toxicological properties with respect to mammals and aquatic animals.
International Application WO-A-98/57969, which is no prior publication, proposes 4-haloalkyl-3-heterocyclylpyridines and -pyrimidines for use as pesticides.
It was an object of the present invention to provide compounds having good insecticidal and acaricidal properties, combined with low toxicity with respect to mammals and aquatic animals.
It has now been found that compounds of the formula (I), if desired also as salts, have, compared with the prior-art compounds, a broader activity spectrum with respect to animal pests, combined with more favorable toxicological properties with respect to mammals and aquatic animals.
Accordingly, the invention provides compounds of the formula (I),
where the symbols and indices are as defined below:
m is 0 or 1;
R
1
and R
2
are
a) H, CH
3
, —C
2
H
5
, —CH
2
—CH
2
—CH
3
, —CH
2
(CH
3
)
2
or cyclopropyl or
b) —CH
3
, —CH
2
XR
3
, —CHY, —CO
2
R
4
or —CONR
5
R
6
,
where in each case one of the radicals R
1
, R
2
is of the group a and the other is of the group b;
X is O, S, SO, SO
2
or NR
7
;
Y is O, BR
2
, —O—(CH
2
)
2
—O—, ((C
1
-C
4
)-alkoxy)
2
, ((C
1
-C
4
)-alkylthio)
2
, V—(CH
2
)
2
or
3
—V, where V=O, S, where an H atom is optionally replaced by (C
1
-C
4
) alkyl;
R
3
is R
8
, COR
9
, CO
2
R
10
, CONR
11
R
12
or, if X is O or NR
7
, SO
2
R
13
,
R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
are identical or different and are independently of one another H, (C
1
-C
10
)-alkyl, (C
2
-C
10
)-alkenyl, (C
2
-C
10
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-C
8
)-cycloalkenyl, (C
6
-C
8
)-cycloalkynyl, aryl or heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, if appropriate, in each case R
5
and R
6
and R
11
and R
12
together are —(CH
2
)
4
—, —(CH
2
)
5
—, —(CH
2
)
2
—O—(CH
2
)
2
— or —(CH
2
)
2
—NR
4
—(CH
2
)
2
;
with the proviso, that the compounds in which
R
1
=CO
2
C
2
H
5
and R
2
=H,
R
1
=H and R
2
=CH
2
NHC
6
H
5
,
R
1
=CH
3
and R
2
=CO
2
H,
R
1
=CH
3
and R
2
=CO
2
C
2
H
5
,
R
1
=CH
3
and R
2
=CON(CH
3
)
2
,
R
1
=CH(CH
3
)
2
and R
2
=CO
2
H,
R
1
=CH(CH
3
)
2
and R
2
=CO
2
C
2
H
5
are not included.
Preferred compounds of the formula (I) are, for example,
1. compounds in which R
1
is H and R
2
is a radical of the group b;
2. compounds in which R
1
is a radical of the group b and R
2
is H,
3. compounds in which R
1
is a radical of the group a, with the exception of hydrogen, and R
2
is a radical of the group b.
m is preferably 0.
If m=1 and R
1
or R
2
=CH
2
S(O)
n
R
3
, n is preferably 2.
From the group a, H, CH
3
and cyclopropyl are preferred. From the group b, CH
2
XR
3
and —CONR
5
R
6
are preferred.
R
4 . . . 13
are preferably
a) H, (C
1
-C
10
)-alkyl, (C
2
-C
10
)-alkenyl, (C
2
-C
10
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-C
8
)-cycloalkenyl, (C
6
-C
8
)-cycloalkynyl, where the six last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of:
halogen, cyano, citro, hydroxyl, —C(═W)R
14
, —C(═NOR
10
)R
14
, —C(═NNR
14
2
)R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
, —OC(═W)R
14
, —OC(═W)OR
14
, —NR
5
C(═W)R
14
, —N[C(═W)R
14
]
2
, —NR
14
C(═W)OR
14
, —C(═W)NR
14
—NR
14
2
, —C(═W)NR
14
—NR
14
[C(═W)R
15
], —NR
14
—C(═W)NR
14
2
, —NR
14
—NR
14
C(═W)R
14
, —NR
14
—N[C(═W)R
14
]
2
, —N[(C═W)R
14
]—NR
14
2
, —NR
14
—NR
14
[(C═W)WR
14
], —NR
14
(C═NR
14
)R
14
, —NR
14
(C═NR
14
)—NR
14
2
, —O—NR
14
2
, —O—NR
14
(C═W)R
14
, —SO
2
NR
14
2
, —NR
14
SO
2
R
14
, —SO
2
OR
14
, —OSO
2
R
14
, —OR
14
, —NR
14
2
, —SR
14
, —SiR
14
3
, —SeR
14
, —PR
14
2
, —P(═W)R
14
2
, —SOR
14
, —SO
2
R
14
, —PW
2
R
14
2
, —PW
3
R
14
2
, aryl and
heterocyclyl,
the two last-mentioned radicals of which are unsubstituted or substituted by one or more radicals from the group consisting of
(C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-C
8
)-cycloalkenyl, (C
6
-C
8
)-cycloalkynyl, (C
1
-C
6
)-haloalkyl, (C
2
-C
6
)-haloalkenyl, (C
2
-C
6
)-haloalkynyl, halogen, —OR
14
, —NR
14
2
, —SR
14
, —SiR
14
3
, —C(═W)R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
, —SOR
14
, —SO
2
R
14
, nitro, cyano and hydroxyl,
b) aryl, which is unsubstituted or substituted by one or more radicals from the group consisting of (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-C
8
)-cycloalkenyl and (C
6
-C
8
)-cycloalkynyl, where these six abovementioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, —C(═W(R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
, —OR
14
, —NR
14
2
, —SR
14
, —SOR
14
and —SO
2
R
14
, halogen, cyano, nitro, —C(═W)R
14
, —C═NOR
10
)R
14
, —C(═NNR
14
2
)R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
, —OC((═W)R
14
, —OC(═W)OR
14
, —NR
14
C(═W)R
14
, —[C(═W)R
14
]
2
, —NR
14
C(═W)OR
14
, —OR
14
, —NR
14
2
, —SR
14
, —SiR
14
3
, —PR
14
2
, —SOR
14
, —SO
2
R
14
, —PW
2
R
14
2
and —PW
3
R
14
2
,
c) heterocyclyl which is unsubstituted or substituted by one or more radicals from the group consisting of
(C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-C
8
)-cycloalkenyl and (C
6
-C
8
)-cycloalkynyl,
where these six abovementioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, —C(═W)R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
), OR
14
, —NR
14
2
, —SR
14
, —SOR
14
and —SO
3
R
14
,
halogen, cyano, nitro, —C(═W(R
14
, —C(═NOR
10
)R
14
, —C(═NNR
14
2
)R
14
, —C(═W)OR
14
, —C(═W)NR
14
2
, —OC(═W)R
14
, —OC(═W)OR
14
, —NR
14
C(═W)R
14
, —[C(═W)R
14
]
2
, —NR
14
C(═W)OR
14
, —OR
14
—NR
14
2
, —SR
14
, SiR
14
3
, —PR
14
2
, —SOR
14
, —SO
2
R
14
, —PW
2
R
14
and —PW
3
R
14
2
,
W is O or S;
R
14
is identical or different and is hydrogen, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
4
-(C
8
)-cycloalkenyl, (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkyl, (C
4
-C
8
)-cycloalkenyl-(C
1
-C
4
)alkyl, (C
3
-C
8
)-cycloalkyl-(C
2
-C
4
)alkenyl, (C
4
-C
8
)-cycloalkenyl-(C
1
-C
4
)-alkenyl, (C
1
-C
6
)-alkyl-(C
3
-C
8
)-cycloalkyl, (C
2
-C
6
)-alkenyl-(C
3
-C
8
)-cycloalkyl, (C
2
-C
6
)-alkynyl-(C
3
-C
8
)-cycloalkyl, (C
1
-C
6
)-alkyl-(C
4
-C
8
)-cycloalkenyl, (C
2
-C
6
)-alkenyl-(C
4
-C
8
)cycloalkenyl, where the fourteen last-mentioned radicals are unsubstituted or substituted by one or more, preferably 1 to 3, radicals from the group consisting of
halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C
1
-C
6
)-alkoxy, (C
2
-C
6
)-alkenyloxy, (C
2
-C
6
)-alkynyloxy, (C
1
-C
6
)-haloalkyloxy, (C
2
-C
6
)-haloalkenyloxy, (C
2
-C
6
)-haloalkynyloxy, (C
3
-C
8
)-cycloalkoxy, (C
4
-C
8
)-cycloalkenyloxy, (C
3
-C
8
)-halocycloalkoxy, (C
4
-C
8
)-halocycloalkenyloxy, (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkoxy, (C
4
-C
8
)-cycloalkenyl-(C
1
-C
4
)-alkoxy, (C
3
-C
8
)-cycloalkyl-(C
2
-C
4
)-alkenyloxy, (C
4
-C
8
)-cycloalkenyl-(C

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