Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2001-05-30
2002-04-09
Davis, Zinna Northington (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C560S035000, C560S042000, C564S147000, C564S182000, C514S538000, C514S615000
Reexamination Certificate
active
06369111
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to novel substituted oximes, to a process for their preparation and to their use as fungicides.
BACKGROUND OF THE INVENTION
It is already known that certain compounds of a similar constitution to those described below have fungicidal properties (compare, for example, EP-A 525516). However, the fungicidal action of these compounds is, in particular at low application rates, not entirely satisfactory.
SUMMARY OF THE INVENTION
Substituted oximes according to the invention have microbicidal activity.
DETAILED DESCRIPTION
This invention, accordingly, provides the novel substituted oximes of the general formula (I),
in which
E represents methoxy, ethoxy, amino or methylamino,
G represents a grouping
in which
R
1
and R
2
are identical or different and independently of one another each represents optionally substituted alkyl, alkenyl, alkinyl, aryl, cycloalkyl, alkylcarbonyl or arylcarbonyl, or
R
1
and R
2
together with the nitrogen atom to which they are attached form a saturated or unsaturated heterocyclic ring, and
Z represents cyano, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfonyl, cycloalkoxy or in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R represents hydrogen, alkyl or in each case optionally substituted cycloalkyl or aryl, and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as in alkoxy or alkylthio.
Halogenoalkyl is partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and chlorine and in particular fluorine. If the halogenoalkyl carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valencies.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen and sulfur. 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 system. A polycyclic ring system can be attached via the heterocyclic ring or a fused-on carbocyclic ring. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Benzoheterocyclyl, as a sub-group of heterocyclyl, represents heterocyclyl to which a phenyl ring is fused.
Dibenzoheterocyclyl represents heterocyclyl to which two phenyl rings are fused.
Furthermore, it has been found that the novel substituted oximes of the general formula (I) are obtained when oximes of the formula (II)
in which
G, R and Z are as defined above,
are reacted with a halogen compound of the general formula (III)
in which
E, L
1
, L
2
, L
3
and L
4
are as defined above and
X represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Compounds of the formula (I) in which E represents amino or methylamino can also be obtained in a simple manner from compounds of the formula (I) in which E represents methoxy or ethoxy, by reaction with ammonia and methylamine, respectively, if appropriate in the presence of a diluent (compare also Tetrahedron Letters 1993, 5151-5154).
Compounds of the formula (I) in which R represents alkylsulfonyl can also be obtained in a simple manner from compounds of the formula (I) in which R represents alkylthio, by generally known oxidation methods.
Compounds of the formula (I) in which R represents alkoxy can also be obtained in a simple manner from compounds of the formula (I) in which R represents alkylsulfonyl, by generally known substitution reaction with alcohols.
Finally, it has been found that the novel substituted oximes of the general formula (I) have highly potent fungicidal action.
If appropriate, the compounds according to the invention can be present as mixtures of different 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 any mixtures of these isomers.
Preference is given to substituted oximes of the formula (I) in which
E represents methoxy, ethoxy, amino or methylamino,
G represents a grouping
in which
R
1
and R
2
are identical or different and independently of one another each represents alkyl or alkylcarbonyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkinyl having 2 to 6 carbon atoms, each of which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms, or represents cycloalkyl having 3 to 8 carbon atoms, which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms, or represents phenyl, phenylalkyl or heterocyclylalkyl having 1 to 4 carbon atoms in the alkyl moiety or phenylcarbonyl, each of which is optionally substituted in the phenyl moiety or heterocyclyl moiety, the substituents being selected from the list below:
halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, or
R
1
and R
2
together with the nitrogen atom to which they are attached form a saturated or unsaturated heterocyclic ring having 5 or 6 ring members,
R represents alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms or phenyl, each of which is optionally mono- to tetrasubstituted by halogen or alkyl, preferably represents methyl or cyclopropyl, in particular methyl,
Z represents cyano, alkoxycarbonyl, alkoxy, alkylthio or alkylsulfonyl having in each case 1 to 4 carbon atoms in the alkyl moiety, cycloalkoxy having 5 or 6 carbon atoms or
represents alkyl or halogenoalkyl having in each case 1 to 4 carbon atoms and being in each case optionally monosubstituted by cyano or alkoxy, or
represents cycloalkyl or cycloalkylalkyl having in each case 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally mono- to tetrasubstituted by halogen or alkyl; or
represents heterocyclyl, benzoheterocyclyl, dibenzoheterocyclyl or heterocyclylalkyl having in each case 3 to 7 ring members in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkyl moiety and being optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 4 carbon atoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl;
or represents aryl or arylalkyl having in each case 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and being in each case optionally mono- to tetrasubstituted in the aryl moiety by identical or different substituents, the possible substituents preferably being selected from the list below:
halogen, cyano, nitro, amino, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkoxya
Backhaus Dirk
Gayer Herbert
Gerdes Peter
Hillebrand Stefan
Mauler-Machnik Astrid
Bayer Aktiengesellschaft
Davis Zinna Northington
Gil Joseph C.
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