Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-04-14
2001-08-07
Gerstl, Robert (Department: 1613)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000, C548S125000
Reexamination Certificate
active
06271226
ABSTRACT:
This application is a 371 of PCT/EP97/05475, which was filed on Oct. 6, 1997.
The invention relates to novel oxime derivatives, to a plurality of processes for their preparation and to their use as fungicides, and also to novel intermediates and to a plurality of processes for their preparation.
It is already known that certain oxime derivatives which are constitutionally similar to those described below have fungicidal properties (cf., for example, WO-A 9504728). However, in many instances the fungicidal activity of these compounds is unsatisfactory.
This invention, accordingly, provides the novel oxime derivatives of the general formula (I)
in which
A represents alkanediyl
Ar represents in each case optionally substituted arylene or heteroarylene,
G represents a single bond, alkanediyl which is optionally interrupted by hetero atoms (but where the carbon atom to which R
1
is attached is in each case linked with a carbon atom of the alkanediyl chain) or a grouping
in which
R
3
represents alkyl,
R
1
represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl,
R
2
represents hydrogen or alkyl,
Y represents oxygen, sulphur or —NH— and
Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, also attached to hetero atoms, such as in alkoxy, alkylthio or alkylamino. If an alkyl or alkanediyl chain is interrupted by more than one hetero atom, these are identical or different. If an alkyl or alkanediyl chain is interrupted by more than one oxygen atom, these are not adjacent to one another.
Halogen generally represents fluorine, chlorine, bromine or iodine, and also pseudohalogens, such as, for example, cyano, preferably fluorine, chlorine, bromine or cyano, in particular 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 which differs from carbon. If the ring contains a plurality of hetero atoms, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form, together with other carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which optionally form a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Furthermore, it has been found that the novel oxime derivatives of the general formula (I) are obtained when (process a)) oximes of the general formula (II)
in which
A, Ar, Y and R
2
are as defined above,
are reacted with an alkylating agent of the general formula (III)
in which
G, R
1
and Z are as defined above and
X represents halogen, alkylsulphonyloxy or optionally substituted arylsulphonyloxy,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Finally, it has been found that the novel oxime derivatives of the general formula (I) have a very strong fungicidal activity.
If appropriate, the compounds according to the invention can be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, or optical isomers. What is claimed are both the E and the Z isomers, the individual enantiomers, the racemates and also any mixtures of these isomers.
The present application preferably provides oxime derivatives of the formula (I) in which
A represents alkanediyl having 1 to 6 carbon atoms,
Ar represents in each case optionally substituted phenylene or naphthylene, represents mono- or bicyclic heteroarylene having in each case 5 or 6 ring members or represents benzo-fused heteroarylene having 5 or 6 ring members at least one of which in each case represents oxygen, sulphur or nitrogen and one or two others optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
G represents a single bond, represents alkanediyl having 1 to 5 chain members which is optionally interrupted by one or two heteroatoms (but where the carbon atom to which R
1
is attached is in each case linked to a carbon atom of the alkanediyl chain) or a grouping
in which
R
3
represents alkyl having 1 to 4 carbon atoms,
R
1
represents hydrogen, cyano, represents in each case optionally halogen-, cyano- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups or represents in each case optionally halogen-, cyano-, carboxyl-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
R
2
represents hydrogen or alkyl having 1 to 4 carbon atoms,
Y represents oxygen, sulphur or —NH— and
Z represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by an identical or different substituent selected from the group consisting of halogen, cyano, hydroxyl, amino, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl and C
1
-C
4
-alkylsulphonyl (each of which may optionally be substituted by halogen);
represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms;
represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogenoalkoxy), C
1
-C
4
-alkyl and C
1
-C
4
-alkoxy-carbonyl;
or represents phenyl, naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members at least one of which represents oxygen, sulphur or nitrogen and one or two others optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having
Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Kruger Bernd-Wieland
Bayer Aktiengesellschaft
Gerstl Robert
Norris & McLaughlin & Marcus
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