Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2000-10-19
2002-06-25
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S615000, C514S640000, C560S035000, C560S042000, C564S249000
Reexamination Certificate
active
06410600
ABSTRACT:
The invention relates to novel azines, to a process for their preparation and to their use as fungicides.
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 unsatisfactory, in particular at low application rates.
This invention, accordingly, provides the novel azines of the general formula (I)
in which
E represents methoxy, ethoxy, NH
2
or NH—CH
3
,
G represents a single bond or 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,
R represents hydrogen, alkyl or in each case optionally substituted cycloalkyl or aryl,
Z represents cyano, alkoxycarbonyl, alkoxy, cycloalkoxy or in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl 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, alkylsulphinyl or alkylsulphonyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are in each straight-chain or branched, including in combination with hetero atoms, such as in alkoxy or alkylthio.
Halogenoalkyl represents 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 in particular fluorine. If the halogenoalkyl carries further substituents, the maximum possible number of the 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 hetero atom, i.e. an atom different from 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 further 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 mono- or bicyclic, aromatic ring systems.
Benzoheterocyclyl as a sub-group of heterocyclyl represents heterocyclyl which is fused to a phenyl ring.
Dibenzoheterocyclyl represents heterocyclyl which is fused to two phenyl rings.
Furthermore, it has been found that the novel azines of the general formula (I) are obtained when hydrazones of the formula (II)
in which
G, R and Z are as defined above are reacted with an aldehyde of the general formula (III)
in which
E, L
1
, L
2
, L
3
and L
4
are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel azines of the general formula (I) have very strong fungicidal activity.
Compounds of the formula (I) in which E represents amino or methylamino can also be prepared in a simple manner from compounds of the formula (I) in which E represents methoxy or ethoxy, by reaction with ammonia, or methylamine, if appropriate in the presence of a diluent (compare also Tetrahedron Letters 1993, 5151-5154).
The compounds according to the invention can, if appropriate, 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 azines of the formula (I), in which
E represents methoxy, ethoxy, NH
2
or NH—CH
3
, in particular methoxy,
G represents a single bond,
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, and in particular represents methyl or cyclopropyl,
Z 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 and being in each case optionally mono- to tetrasubstituted by halogen or alkyl; or
represents heterocyclyl, benzoheterocyclyl, dibenzoheterocyclyl or hetero-cycloalkyl 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, alkylsulphinyl or alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl 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 case optionally mono- to tetrasubstituted in the aryl moiety by identical or different substituents, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy 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, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
in each case doubly attached alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl;
phenoxy or phenylalkoxy having 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms,
heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulphinyl or heterocyclylsulphonyl having 5 or 6 ring members, each of which is optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms or phenyl,
or a grouping
in which
A
1
represents hydrogen or alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, methyl, phenyl, benzyl, alkoxy, alkylamino, dialkylamino having 1 to 4 carbon atoms in the respective alkyl chains and
L
1
, L
2
, L
3
and L
4
are identical or different and independ
Backhaus Dirk
Gayer Herbert
Gerdes Peter
Krüger Bernd-Wieland
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Patel Sudhaker B.
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