Substituted 1,3-dioxan-5-ylamino-hererocyclic compounds,...

Details Substituted 1,3-dioxan-5-ylamino-hererocyclic compounds,... Substituted 1,3-dioxan-5-ylamino-hererocyclic compounds,...

1998-09-25

2001-08-28

Raymond, Richard L. (Department: 1611)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S256000, C514S336000, C514S063000, C544S229000, C544S287000, C544S326000, C544S327000, C544S328000, C546S014000, C546S256000, C546S282400

Reexamination Certificate

active

06281221

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel substituted 1,3-dioxan-5-ylamino-heterocyclic compounds, processes for their preparation and their use as pest control compositions and fungicides.
BACKGROUND OF THE INVENTION
It is already known that certain cycloamino- and -alkoxy-heterocyclic compounds show a fungicidal, acaricidal and insecticidal action (DE-A-42 08 254, incorporated herein by reference). However, the biological action of these compounds is not satisfactory in all examples of use, especially when low amounts are applied and at low concentrations.
SUMMARY OF THE INVENTION
Novel 1,3-dioxan-5-ylamino-heterocyclic compounds have been found of the formula I
in which the radicals and groups are as defined below.
OBJECTS OF THE INVENTION
The invention provides compounds which have a very good plant tolerance and favourable toxicity with respect to warm-blooded animals and are particularly suitable for control of animal pests, such as insects, arachnids, nematodes, helminths and mollusks, for control of endo- and ectoparasites in the veterinary medicine field and for control of harmful fungi.
The foregoing and other objects and advantages of the invention will be set forth in or apparent from the following description.
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 each 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
8
)-trialkylsilylalkynyl, preferably dimethyl-(C
1
-C
8
)-alkyl-silyl-alkynyl, phenyl-(C
1
-C
8
)-dialkyl-silyl-alkynyl, preferably phenyl-dimethyl-silyl-alkynyl, aryl-(C
1
-C
2
)-alkyl-(C
1
-C
8
)-dialkyl-silyl-alkynyl, preferably benzyl-dimethyl-silyl-alkynyl, (C
3
-C
8
)-cycloalkyl-(C
1
-C
8
)-dialkyl-silyl-alkynyl, preferably (C
3
-C
8
)-cycloalkyl-dimethyl-silyl-alkynyl, (1-methyl-sila-(C
3
-C
8
)-cycloalkyl-1-yl)-alkynyl, preferably (1-methyl-silacyclopent-1-yl)-alkynyl or (1-methyl-sila-cyclohex-1-yl)-alkynyl, triphenylsilylalkynyl, (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
1
-C
4
)-haloalkanoyl, (C
3
-C
5
)-cyclo-alkyl, (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
)-alkyl-sulfinyl, (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 isocyclic ring which, if it is a 5-membered ring, can contain one 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 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 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 and Z are oxygen or a group S(O)
m
, where m=0, 1 or 2;
R
4
, R
4′
and R
5
are substituents of the heteroaliphatic ring system;
R
4
and R
4′
are hydrogen, halogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-alkylthio;
R
5
is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned can be unsubstituted or provided with up to three, in the case of fluorine also up to the maximum number of, identical or different radicals, and in the alkyl, alkenyl or alkynyl radicals mentioned, one or more, preferably up to three, non-adjacent saturated carbon units can be replaced by a carbonyl group or by heteroatom units, such as oxygen, S(O)
x
, where x=0, 1 or 2, NR
6
or SiR
7
R
8
, in which R
6
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy or (C
1
-C
4
)-alkanoyl and R
7
and R
8
are (C
1
-C
4
)-alkyl, preferably methyl; and wherein, furthermore, 3 to 12 atoms of these hydrocarbon radicals optionally modified as above can form a ring, and these hydrocarbon radicals, with or without the variations mentioned, can optionally 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 from the series consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl-sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano and nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned 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, or R
4
and R
5
together form a three- to eight-membered ring system which is linked spirocyclically to the ring system containing the heteroatoms Y and Z and in which one or two CH
2
groups, preferably one CH
2
group, can be replaced by heteroatom units, such as oxygen, S(O)
n
, where n=0, 1 or 2, or NR
9
, in which R
9
is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals 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, and the ring system formed from R
4
and R
5
can be unsubstituted or provided with up to three, but preferably one, substituent(s), and these substituents are identical or different and are in each case alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned 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, or the ring system formed from R
4
and R
5
, together with a further benzene ring or cyclohexane ring, forms a fused ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, dekalin 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, and salts thereof, preferably acid addition salts; in particular those compounds for which
R
5
is (C
1
-C
20
)-alkyl, (C
2
-C
20
)-alkenyl, (C
2
-C
20
)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned can be unsubstituted or provided with up to three, in the case of fluorine also up to the maximum number of, identical or different radicals, and in the alkyl, alkenyl or alkynyl rad

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