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

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

1997-04-01

2001-03-27

Ford, John M (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S258100, C514S259500, C514S269000, C514S212020, C514S183000, C540S466000, C540S543000, C540S453000, C540S503000, C540S229000, C540S229000, C540S229000, C540S229000, C540S229000, C540S229000, C540S229000, C540S326000, C540S327000, C540S328000, C540S329000, C540S319000, C540S229000, C540S230000, C540S334000

Reexamination Certificate

active

06207668

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 insectidal action (U.S. Pat. No. 5,571,825). However, the biological activity of these compound is not satisfactory in all respects, in particular when low rates and concentrations are applied.
There have been found novel substituted pyridines/pyrimidines of the formula I
where the radicals and groups are as defined below and which are highly suitable for controlling animal pests such as insects, arachnids, nematodes, helminths and mollusks and their eggs, for controlling endo- and ectoparasites in the veterinary medicine sector and for controlling harmful fungi while having 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
independently of one another are 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
3
-C
5
)-halocycloalkyl, (C
4
-C
5
)-cyCloalkenyl, (C
4
-C
5
)-halocycloalkenyl, (C
3
-C
5
)cycloalkoxy, cyano, cyan-(C
1
-C
4
)-alkyl, nitro, nitro-(C
1
-C
4
)-alkyl, thiocyano, thiocyano-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkoxycarbonyl-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkoxycarbonyl, (C
1
-C
4
)-alkylthio, (C
1
-C
4
)-haloalkylthio, (C
1
-C
4
)-alkylthio-C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio-(C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkylsulfinyl, (C
1
-C
4
)-haloalkylsulfinyl, (C
1
-C
4
)-alkylsulfonyl, (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 and these radicals being (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, preferably trifluoromethyl, halogen, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-haloalkoxy; 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, oxygen or S(O)
q
where q=0, 1 or 2;
Y is a direct bond or CH
2
;
Z is oxygen, NR
7
, S(O)
m
where m=0, 1 or 2;
R
4
,R
5
and W-R
6
are substituents of the heteroaliphatic ring system, where
R
4
and R
5
independently of one another are hydrogen, 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
)-haloalkynyl, (C
3
-C
6
)-cycloalkyl, (C
4
-C
6
)-cycloalkenyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkanoyloxy, (C
1
-C
4
)-haloalkanoyloxy, (C
1
-C
4
)-alkylthio or (C
1
-C
4
)-haloalkylthio;
W is a direct bond, oxygen, —NR
12
—, —CO—, —COO—, CONR
12
—, sulfur, —C=N—, —C=N—O— or —NR
12
O—;
R
6
is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or 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=0, 1 or 2, NR
13
or SiR
14
R
15
, and it being possible for these last-mentioned 5 radicals, with or without the abovementioned variations, optionally to be 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
16
, or
R
6
can be aryl or heterocyclyl, it being possible for these two radicals to be unsubstituted or substituted by up to three, in the case of fluorine also up to the maximum number of, identical or different radicals D
2
R
17
, or
R
4
and R
6
together form a three- to eight-membered ring system which is linked spirocyclically to the ring system which contains the hetero atoms Y and Z and 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)
n
where n=0, 1 or 2, or NR
18
,
where
R
7
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
)-alkanoyl, (C
2
-C
4
)-haloalkanoyl, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylsulfonyl, (C
1
-C
4
)-haloalkylsulfonyl, phenylcarbonyl, phenyl-(C
1
-C
4
)-alkyl or, if A is N, also phenyl, it being possible for the last-mentioned 3 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 substituents R
11
, or
R
7
is CONR
8
R
9
, in which
R
8
and R
9
independently of one another are hydrogen, (C
1
-C
4
)-alkyl or phenyl, it being possible for the phenyl group to be unsubstituted or substituted by up to three, in the case of fluorine also up to the maximum number of, identical or different substituents R
10
, and
R
10
and R
11
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, (C
1
-C
4
)-alkylthio or halogen;
R
12
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkanoyl or (C
3
-C
5
)-cycloalkyl;
R
13
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-alkanoyl;
R
14
and R
15
independently of one another are (C
1
-C
4
)-alkyl, preferably methyl;
R
18
is hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, it being possible for the last-mentioned 3 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
19
;
R
19
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, and the ring system formed by R
4
and R
6
can be unsubstituted or provided with up to three substituents, but preferably one substituent, D
3
R
20
, or the ring system formed by R
4
and R
6
together with a further benzene ring or cydohexane ring forms a fused ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and the benzene ring in these fused systems can be unsubstituted or provided with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents D
4
R
21
, where
D
1
, D
2,
D
3
and D
4
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, SO
2
NR
22
, NR
22
SO
2
, NR
22
O, ONR
22
, NR
22
, NR
22
CO, CONR
22
or SiR
23
R
24
, where k is 0, 1 or 2; and
R
16
, R
17
, R
20
and R
21
in each case independently of one another are hydrogen, cyano, nitro, halogen, (C
1
-C
8
)-alkyl, (C
1
-C
8
)-haloalkyl, (C
2
-C
8
)-alkenyl, (C
2
-C
8
)-haloalkenyl, (C
2
-C
8
)alkynyl, (C
2
-C
8
)-haloalkynyl, (C
1
-C
8
)-alkoxy (C
1
-C
4
)-alkyl, (C
1
-C
8
)-haloalkoxy(C
1
-C
4
)-alkyl, (C
1
-C
8
)-alkylthio(C
1
-C
4
)-alkyl, (C
1
-C
8
)-haloalkylthio(C
1
-C
4
)-alkyl, (C
3
-C
8
)-cycloalkyl

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