Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-04-09
2001-02-27
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S460000, C514S448000, C549S029000, C549S065000, C549S072000, C549S074000, C549S076000, C549S078000, C546S001000
Reexamination Certificate
active
06194443
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel arninophenol derivatives, to a process for their preparation and to their use as fungicides.
BACKGROUND OF THE INVENTION
It is already known that certain aminophenol derivatives have fungicidal activity (compare, for example, EP-A 293718).
However, the activity of these prior-art compounds, in particular at low application rates and concentrations, is not entirely satisfactory in all areas of use.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides the novel arninophenol derivatives of the general formula (I)
in which
y
1
, Y
2
, Y
3
and Y
4
independently of one another each represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio,
R
1
represents in each case optionally substituted alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl or heterocyclyl and
Z represents a grouping
in which
R
2
represents alkyl, alkoxy or alkylthio, each of which is optionally interrupted by oxygen atoms, and
R
3
represents alkyl which is optionally interrupted by oxygen atoms, or
Z represents a grouping
in which
R
4
represents alkyl which is optionally interrupted by oxygen atoms, or
Z represents a grouping
in which
Het represents optionally substituted heterocyclyl,
A represents a single bond, oxygen, sulphur, alkanediyl or represents
where
R
5
represents hydrogen or alkyl, and
Q represents oxygen or sulphur.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, including those in combination with hetero atoms, such as in alkoxy, alkylthio or alkylarnino, are in each case straight-chain or branched. If the hydrocarbon chains are interrupted by oxygen atoms, the oxygen atoms are not in a terminal position, and two oxygen atoms in a chain are in each case interrupted by at least two carbon atoms.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine and in particular represents fluorine or chlorine.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a hetero atom, i.e. an atom other than carbon. If the ring contains a plurality of hetero atoms, these can be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. If the ring contains a plurality of oxygen atoms, these are not adjacent. If appropriate, the cyclic compounds form, together with other carbocyclic or heterocyclic fused-on or bridged rings, a polycyclic ring systemn Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated, carbocyclic compounds which, if appropriate, form a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Furthermore, it has been found that the novel compounds of the general formula (I) are obtained when a) hydroxyl compounds of the general formula (II)
in which
R
1
, Y
1
, Y
2
, Y
3
and Y
4
are each as defined above,
are reacted with a halogen compound of the general formula (III)
Z—X
1
(III),
in which
Z is as defined above and
X
1
represents halogen,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when b)
amino compounds of the general formula (IV)
in which
Y
1
, Y
2
, Y
3,
Y
4
and Z are each as defined above,
are reacted with a carboxylic acid derivative of the general formula (V)
in which
R
1
is as defined above and
X
2
represents halogen or
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
Finally, it has been found that the novel compounds of the general formula (I) have very strong fungicidal activity.
If appropriate, the compounds according to the invention are present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers. What is claimed are both the E and the Z isomers, and also the threo and erythro and the optical isomers, and any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
Y
1
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
Y
2
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
Y
3
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
Y
4
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case from 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
where at least two of the radicals Y
1
to Y
4
represent halogen,
R
1
represents in each case optionally mono- to pentasubstituted alkyl or alkenyl having in each case 4 to 10 carbon atoms, and the possible substituents are preferably selected from the following list: halogen, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 2 carbon atoms and 1 to 5 halogen atoms or optionally halogen- or alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, where the carbon atom which is attached to the carbonyl group does not carry a hydrogen atom, or
R
1
represents in each case optionally mono- to pentasubstituted cycloalkyl or cycloalkenyl having in each case 3 to 12 carbon atoms, and the possible substituents are preferably selected from the following list: halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 2 carbon atoms and 1 to 5 halogen atoms or optionally halogen- or alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, and
Z represents a grouping
in which
R
2
represents alkyl, alkoxy or alkylthio having 1 to 8 carbon atoms, each of which is optionally interrupted by 1 to 2 oxygen atoms, and
R
3
represents alkyl having 1 to 8 carbon atoms which is optionally interrupted by 1 to 2 oxygen atoms, or
Z represents a grouping
R
4
—O—CH
2
—,
in which
R
4
represents alkyl having 1 to 8 carbon atoms which is optionally interrupted by 1 to 2 oxygen atoms.
The present invention also preferably provides compounds of the formula (I) in which
Y
1
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
Y
2
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different halogen atoms,
Y
3
represents hydrogen, halogen, alkyl, alkoxy, alkylthio having in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 3 carbon atoms and 1 to 5 identical or different hal
Dehne Heinz-Wilhelm
Kruger Bernd-Wieland
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Patel Sudhaker B.
Raymond Richard L.
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