Substituted pyridines/pyrimidines, their preparation and...

Details Substituted pyridines/pyrimidines, their preparation and... Substituted pyridines/pyrimidines, their preparation and...

1998-10-23

2001-07-24

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S256000, C544S002000, C544S008000, C544S182000, C544S316000, C544S317000, C544S318000, C544S319000, C546S290000, C546S297000

Reexamination Certificate

active

06265398

ABSTRACT:

The invention relates to novel substituted pyridines/pyrimidines, to processes for their preparation, and to their use as pesticides, fungicides and ovicides.
It has already been disclosed that certain cycloalkylamino and -alkoxy heterocycles have a fungicidal, acaricidal and insecticidal activity (U.S. Pat. No. 5,571,815). However, the biological activity of these compounds is not satisfactory for all exemples of use, in particular when low rates and concentrations are applied.
There have been found novel substituted pyridines/pyrimidines of the formula I
in which the radicals and groups are as defined below and which are highly suitable for controlling animal pests such as insects, arachnids, nematodes, helminths and molluscs and eggs of these, for controlling endo- and ectoparasites in the field of veterinary medicine and for controlling harmful fungi while showing good plant tolerance and favorable toxicity to warm-blooded species.
The invention therefore relates to compounds of the formula I in which
R
1
is hydrogen, halogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl or (C
3
-C
5
)-cycloalkyl;
R
2
and R
3
are identical or different and are in each case hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-haloalkenyl, (C
2
-C
4
)-alkynyl, (C
2
-C
4
)-haloalkynyl, tri-(C
1
-C
4
)-alkylsilyl-(C
2
-C
4
)-alkynyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-haloalkoxy-(C
1
-C
4
)-haloalkyl, halogen, hydroxyl, (C
1
-C
4
)-hydroxyalkyl, (C
1
-C
4
)-alkanoyl, (C
1
-C
4
)-alkanoyl-(C
1
-C
4
)-alkyl, (C
2
-C
4
)-haloalkanoyl, (C
3
-C
5
)-cycloalkyl, (C
4
-C
5
)-cycloalkenyl, (C
3
-C
5
)-cycloalkoxy, (C
3
-C
5
)-halocycloalkyl, (C
4
-C
5
)-halocycloalkenyl, cyano, (C
1
-C
4
)-cyanoalkyl, nitro, (C
1
-C
4
)-nitroalkyl, thiocyano, (C
1
-C
4
)-thiocyanoalkyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkoxycarbonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkoxycarbonyl, (C
1
-C
4
)alkanoyloxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio (C
1
-C
4
)-alkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkylthio, (C
1
-C
4
)-alkylsulfinyl, (C
1
-C
4
)-haloalkylsulfinyl, (C
1
-C
4
)-alkylsulfonyl or (C
1
-C
4
)-haloalkylsulfonyl; or
R
2
and R
3
together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered carbocyclic ring which, if it is a 5-membered ring, can contain an oxygen or sulfur atom instead of CH
2
or which, if it is a 6-membered ring, can contain one or two nitrogen atoms instead of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals R
27
, or
R
2
and R
3
together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered carbocyclic ring which can contain oxygen and/or sulfur instead of one or two CH
2
groups and which is optionally substituted by 1, 2 or 3 (C
1
-C
4
)-alkyl groups;
A is CH or N;
X is NH, O or S(O)
q
where q is 0, 1 or 2;
Y
1
, Y
2
and Y
3
independently of one another are a group of the formula —O—, —CO—, —CNR
6
—, —S(O)
r
—, —N(O)
l
R
6
— or CR
7
R
8
where r is 0, 1 or 2 and l is 0 or 1 or
Y
1
or Y
3
replace a direct bond;
R
4
is hydrogen or (C
1
-C
4
)-alkyl;
m is 0, 1, 2, 3 or 4, preferably 1 or 2;
n is 0, 1, 2, 3 or 4, preferably 1 or 2;
Z is a direct bond, NR
9
, O, S(O)
s
where s is 0, 1 or 2, OSO
2
, SO
2
O, NR
10
SO
2
, SO
2
NR
11
, SiR
12
R
13
, U
1
P(W
1
)V
1
V
2
or
 where
U
1
, U
2
independently of one another are a direct bond, NR
14
or O;
W
1
, W
2
independently of one another are oxygen or sulfur, preferably oxygen;
V
1
, V
2
, V
3
are identical or different and are a direct bond, NR
15
or oxygen, where
R
9
, R
10
, R
11
, R
14
and R
15
are identical or different and are in each case hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
R
5
radicals are substituents which are independent of one another and are halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and it being possible for one or more, preferably up to three, non-adjacent saturated carbon units in the last-mentioned 5 radicals to be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)
x
where x is 0, 1 or 2, NR
16
or SiR
17
R
18
, and it being possible for these last-mentioned 5 radicals, with or without the abovementioned variations, to be optionally substituted by one or more, preferably up to three, in the case of fluorine up to the maximum number of, identical or different radicals D
1
R
19
, or
R
5
can be aryl or heterocyclyl, it being possible for these two radicals to be unsubstituted or to be substituted by up to three, in the case of fluorine also up to the maximum number of, identical or different radicals D
2
R
20
, or two adjacent radicals
Z—R
5
together with the carbon atoms to which they are attached can form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)-alkyl and oxo, or
R
9
, R
10
, R
11
, R
14
or R
15
independently of one another together with the R
5
which is attached to Z can form a 4- to 8-membered ring system in which one or two CH
2
groups, preferably one CH
2
group, can be replaced by hetero atom units such as oxygen, S(O)
t
where t is 0, 1 or 2 or NR
25
, where
R
6
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-haloalkenyl, (C
2
-C
4
)-alkynyl, (C
2
-C
4
)-haloalkynyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkylthio, (C
1
-C
4
)-haloalkylthio, (C
1
-C
4
)-alkanoyl, (C
2
-C
4
)-haloalkanoyl, (C
3
-C
5
)-cycloalkyl, (C
1
-C
4
)-alkylsulfonyl, (C
1
-C
4
)-haloalkylsulfonyl (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxycarbonyl;
R
7
and R
8
independently of one another are hydrogen, hydroxyl, halogen, cyano, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-haloalkenyl, (C
2
-C
4
)-alkynyl, (C
2
-C
4
)-haloalkenyl, (C
3
-C
5
)-cycloalkyl, (C
1
-C
4
)-alkanoyl, (C
1
-C
4
)-haloalkanoyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkylthio or (C
1
-C
4
)-haloalkylthio;
R
12
and R
13
independently of one another are (C
1
-C
4
)-alkyl or phenyl, preferably methyl;
R
16
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-alkanoyl;
R
17
and R
18
independently of one another are (C
1
-C
4
)-alkyl, preferably methyl;
D
1
and D
2
are in each case independent of one another and are a direct bond, oxygen, S(O)
k
, SO
2
O, OSO
2
, CO, OCO, COO, NR
21
, SO
2
NR
21
, NR
21
SO
2
, ONR
21
, NR
21
O, NR
21
CO, CONR
21
or SiR
22
R
23
and k is 0, 1 or 2, where
R
21
radicals independently of one another are hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkanoyl or (C
3
-C
5
)-cycloalkyl;
R
22
and R
23
independently of one another are (C
1
-C
4
)-alkyl;
R
19
and R
20
independently of one another are hydrogen, cyano, nitro, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, it being possible for the cycloaliphatic, aromatic or heterocyclic ring systems in the last-mentioned 8 radicals to be unsubstituted or to be provided with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents R
24
, or
R
19
and R
20
, attached to the same carbon atom, together are an oxo group; where
R
24
radicals independently of one another can be (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, cyano, nitro or halogen;
R
25
independently of one another can be hydrogen, (C
1
-C
8
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkylthio, (C
3
-C
5
)-cycloalkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-alkynyl, (C
1
-C
4
)-alkanoyl, (C
1
-C
4
)-ha

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