Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-04-01
2001-10-09
Travers, Russell (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S259500, C514S269000, C514S315000, C514S318000
Reexamination Certificate
active
06300333
ABSTRACT:
DESCRIPTION
Substituted piperidines, processes for their preparation and their use as pesticides and fungicides.
The invention relates to substituted piperidines, to processes for their preparation and to their use as pesticides and fungicides.
It has already been disclosed that certain 4-(piperidin-4-ylamino)-pyrimidines have fungicidal, acaricidal and insecticidal activity (DE-A42 08 254). However, the biological action of these compounds is not always satisfactory in all exemplary applications, in particular when low application rates and concentrations are used.
There have been found (piperidin-4-ylamino) heterocycles 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, helminth and mollusks, for controlling endoparasites and ectoparasites in the veterinary medicine field and for controlling harmful fungi, while being well tolerated by plants and having 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
8
)-alkyl, (C
1
-C
8
)-haloalkyl, (C
1
-C
8
)-alkoxy or (C
3
-C
6
)-cycloalkyl;
R
2
and R
3
are identical or different and in each case are hydrogen, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl, (C
2
-C
8
)-alkynyl, (C
1
-C
8
)-alkoxy, halogen, hydroxyl, cyano, nitro, thiocyano, (C
1
-C
8
)-alkanoyl, (C
1
-C
8
)-alkoxycarbonyl, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl, amino, (C
1
-C
8
)-alkylamino, (C
1
-C
8
)-dialkylamino or (C
3
-C
6
)-cycloalkyl,
it being possible for a saturated carbon unit in the alkyl, cycloalkyl, alkenyl and alkynyl radicals or the groups derived from these, such as the alkoxy, alkylthio, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, to be replaced by a hetero atom unit such as oxygen, S(O)
x
, where x=0, 1 or 2 or dimethylsilyl, and it furthermore being possible for up to three hydrogen atoms in these radicals or in the groups derived from these to be replaced by halogen, in the case of fluorine it also being possible for all hydrogen atoms to be replaced by fluorine; or
R
2
and R
3
together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-membered ring, may contain an oxygen or sulfur atom in place of CH
2
or which, if it is a 6-membered ring, may contain one or two nitrogen atoms in place of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals are (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 isocyclic ring which may contain oxygen and/or sulfur in place 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 and Z are identical or different and are in each case oxygen, sulfur or a group NR
5′
or NR
5″
where R
5′
and R
5″
are identical or different and in each case have the meanings given hereinbelow for R
5
; or, in the event that Y is sulfur or a group NR
5′
, Z may also be a direct bond, or, in the event that Y is a group NR
5′
, R
5′
may additionally also be nitro, cyano, hydroxyl, alkoxy or a group NR
5′″
R
5′″
where R
5′″
and R
5′″
are identical or different and in each case may have the meanings given hereinbelow for R
5
,
m and n are identical or different and are the numbers 1, 2, 3, 4 or 5 and the total of m and n does not exceed the number 6;
R
4
and R
4′
are identical or different and are in each case hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, halogen or (C
1
-C
4
)-alkoxy;
R
5
is alkyl, alkenyl, alkynyl, aryl, heterocyclyl, it being possible for the aryl or heterocyclyl radicals mentioned to be unsubstituted or to have attached to them up to three, in the case of fluorine also up to the maximum number of, identical or different radicals, and it being possible, in the alkyl, alkenyl or alkynyl radicals mentioned, for one or more, preferably up to three, non-adjacent saturated carbon units 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
6
or SiR
7
R
8
, R
6
being hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-alkanoyl and R
7
and R
8
being (C
1
-C
4
)-alkyl, preferably methyl;
and in which, in addition, 3 to 12 atoms of these hydrocarbon radicals which are optionally modified as above may form a cycle;
and it being possible for these hydrocarbon 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 selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, halogenalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, it being possible for the cycloaliphatic, aromatic or heterocyclic ring systems amongst the substituents which have just been mentioned to be unsubstituted or to have attached to them up to three, in the case of fluorine also up to the maximum number of, identical or different substituents,
and it furthermore being possible, in the event that Y is a group NR
5′
, R
5′
of group Y and R
5
of group Z to be linked to form a 5-8-membered heteroaliphatic ring system; or it being possible, in the event that Z is a group NR
5″
, for R
5″
and R
5
l to be linked cyclically to form a 3-8-membered ring system and it being possible for one saturated carbon unit in this ring system to be replaced by oxygen, sulfur or a group NG in which G is an optionally substituted phenyl group, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkanoyl or (C
1
-C
4
)-alkoxycarbonyl and it being possible for this ring system to be optionally benzo-fused,
and their tautomers and salts, preferably acid addition salts;
in particular those compounds where
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 in each case 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, trimethylsilylalkynyl, (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
)haloalkanoyl, (C
3
-C
5
)-cycloal kyl, (C
3
-C
5
)-halocycloalkyl, 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
)-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, (C
1
-C
4
)-haloalkylsulfonyl, amino, (C
1
-C
4
)-alkylamino or (C
1
-C
4
)-dialkylamino; or
R
2
and R
3
together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-membered ring, may contain an
Bonin Werner
Braun Ralf
Jakobi Harald
Kern Manfred
Krautstrunk Gerhard
Frommer & Lawrence & Haug LLP
Hoechst Schering AgrEvo GmbH
Travers Russell
Wang Shengjun
LandOfFree
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