4-Haloalkyl-3-heterocyclylpyridines and...

Details 4-Haloalkyl-3-heterocyclylpyridines and... 4-Haloalkyl-3-heterocyclylpyridines and...

2001-03-14

2003-02-18

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S256000, C544S242000, C544S333000, C544S335000

Reexamination Certificate

active

06521610

ABSTRACT:

DESCRIPTION
The present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines, to processes for their preparation, to compositions comprising them and to the use of novel and known 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.
It is already known that appropriately substituted pyridines or pyrimidines have acaricidal and insecticidal activity. Thus, WO 95/07891 describes pyridines which carry a cycloalkyl radical in position 4 which is linked via a hetero atom and a group of various substituents in position 3. WO 93119050 discloses 4-cycloalkylamino-and 4-cycloalkoxypyrimidines which carry in position 5 inter alia alkyl, alkoxy or haloalkoxy groups. However, the desired activity against the harmful organisms is not always sufficient. Additionally, these compounds often have undesirable toxicologic properties toward mammals and aquatic living beings.
Pyridyl-1,2,4-thiadiazoles having fungicidal properties are described in DE-A 42 39 727. The compounds disclosed therein carry the thiadiazole ring in position 2, 3 or 4 of the unsubstituted pyridine.
EP-A 0 371 925 discloses some 1,3,4-oxadiazolyl- and 1,3,4-thiadiazolyl-pyrimidines having nematicidal and fungicidal properties. In the biologically effective compounds disclosed in this publication, the pyrimidine carries the oxadiazolyl or thiadiazolyl ring either
a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or
b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.
Aryltriazole derivatives for use as pesticides are known from EP-A 0,185,256. In addition to the phenyltriazoles, which are particularly preferred, three haloalkyl-3-pyridyltriazoles are disclosed:
3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole
3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and
3-(2-chloro4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,
their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.
Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:
3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole
3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole
5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazole
5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole
2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole
2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole
2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole
2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole
2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole
2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole
2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide
ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate
N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)4-methyl-5-thiazolyl]carbonylhydrazine
2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide
4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole
4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-py(idyl)thiazole
N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine
2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene
2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1 -methyl-1 H-1,3,4-triazole
2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and
2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.
However, a biological activity toward harmful organisms has hitherto not been disclosed.
It is an object of the present invention to provide compounds having good insecticidal and acaricidal properties and simultaneously low toxicity toward mammals and aquatic living beings.
It has now been found that compounds of the formula I, optionally as salts, have a wider activity spectrum against animal pests and simultaneously more favorable toxicologic properties toward mammals and aquatic living beings than the prior art compounds.
In the formula (I):
Y is halo-C
1
-C
6
-alkyl;
x is CH or N;
m is 0 or 1;
Q is a 5-membered heterocyclic group
in which
a) X
1
= W,
X
2
= NR
a
,
X
3
= CR
b
R
1
or
b) X
1
= NR
a
,
X
2
= CR
b
R
1
,
X
3
= W
or
c) X
1
= V,
X
2
= CR
a
R
1
,
X
3
= NR
b
or
d) X
1
= V,
X
2
= CR
a
R
2
,
X
3
= CR
b
R
3
or
e) X
1
= V,
X
2
= CR
4
R
5
,
X
3
= CR
6
R
7
or
f) X
1
= NR
a
,
X
2
= CR
b
R
1
,
X
3
= NR
8
;
R
a
and R
b
together are a bond
V is oxygen, sulfur or NR
9
;
W is oxygen or sulfur;
R
1
is hydrogen,
(C
1
-C
20
)-alkyl, (C
2
-C
20
)-alkenyl, (C
2
-C
20
)-alkynyl, (C
3
-C
8
)-cycloalkyl,
(C
4
-C
8
)-cycloalkenyl, (C
6
-C
8
)-cycloalkynyl,
where the six last-mentioned radicals are optionally substituted by one or more radicals from the group
halogen, cyano, nitro, hydroxyl, —C(═W)R
10
, —C(═NOR
10
)R
10
, —(═NNR
10
2
)R
10
, —C(═W)OR
10
, —C(═W)NR
10
2
, —OC(═W)R
10
, —OC(═W)OR
10
, —NR
10
C(═W)R
10
, —N[C(═W)R
10
]
2
, —NR
10
C(═W)OR
10
, —C(═W)NR
10
—NR
10
C(═W)NR
10
—NR
10
[C(═W)R
10
], —NR
10
—C(═W)NR
10
2
, —NR
10
—NR
10
C(═W)R
10
, —NR
10
—N[C(═W)R
10
]
2
, —N[(C═W)R
10
]—NR
10
2
, —NR
10
—NR
10
[(C═W)R
10
], —NR
10
—NR
10
[(C═W)WR
10
], —NR
10
—R
10
[(C═W)NR
10
2
], —NR
10
(C═NR
10
)R
10
, —NR
10
(C═NR
10
)NR
10
2
, —O—NR
10
2
, —O—NR
10
(C═W)R
10
, —SO
2
NR
10
2
, —NR
10
SO
2
R
10
, —SO
2
OR
10
, —OSO
2
R
10
—OR
10
, —NR
10
2
, —SR
10
, —SiR
10
3
, —SeR
10
, —PR
10
2
, —P(═W)R
10
2
, —SOR
10
, —SO
2
R
10
, —PW
2
R
10
2
, —PW
3
R
10
2
, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group
(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
10
, —NR
10
2
, —SR
10
, —SiR
10
3
, —C(═W)R
10
, —C(═W)OR
10
, —C(═W)NR
10
2
, —SOR
10
, —SO
2
R
10
, nitro, cyano and hydroxyl, aryl,
which is optionally substituted by one or more radicals from the group (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 optionally substituted by one or more radicals from the group
halogen, cyano, nitro, —C(═W)R
10
, —C(═W)OR
10
, —C(═W)NR
10
2
, —OR
10
, —NR
10
2
, —SR
10
, —SOR
10
and —SO
2
R
10
,
halogen, cyano, nitro, —(═W)R
10
, —C(═NOR
10
)R
10
, —C(═NNR
10
2
)R
10
, —C(═W)OR
10
, —C(═W)NR
10
2
, —OC(═W)R
10
, —OC(═W)OR
10
, —NR
10
C(

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