Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-04-06
2002-07-16
Raymond, Richard L (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000, C564S250000, C564S251000
Reexamination Certificate
active
06420362
ABSTRACT:
The invention relates to new azines, a process for their preparation and their use as fungicides.
It has already been disclosed that certain compounds which are structurally similar to those described below have fungicidal properties (compare, for example, WO 95-04728, WO 97-00866). However, the fungicidal action of these compounds leaves something to be desired, especially when low amounts are applied.
The new azines of the general formula (I)
in which
G represents a single bond or a grouping
wherein
R
1
represents in each case optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl,
R represents alkyl or optionally substituted cycloalkyl having 3 to 5 carbon atoms,
Z represents in each case optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another in each case represent hydrogen, halogen, cyano, nitro or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
have now been found.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, also when linked with heteroatoms, such as in alkoxy or alkylthio, are in each case straight-chain or branched.
Halogenoalkyl represents partly or completely 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 also carries further substituents, the maximum possible number of halogen atoms is reduced to the free valencies remaining.
Halogen in general represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Heterocyclyl represents saturated or unsaturated and aromatic, cyclic compounds in which at least one ring member is a heteroatom, that is to say an atom other than carbon. If the ring contains several heteroatoms, these can be identical or different. Heteroatoms are preferably oxygen, nitrogen or sulphur. If the ring contains several oxygen atoms, these are not adjacent. If appropriate, the cyclic compounds form a polycyclic ring system together with further carbocyclic or heterocyclic, fuzed-on or bridged rings. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.
It has furthermore been found that the new azines of the general formula (I) are obtained by a process in which
a) ketones of the general formula (II)
in which
G, R and Z have the abovementioned meanings,
are reacted with an aldehyde of the general formula (III)
in which
L
1
, L
2
, L
3
and L
4
have the abovementioned meanings,
and hydrazine or hydrazine hydrate,
optionally in the presence of a diluent and optionally in the presence of a catalyst, or by a process in which
b) hydrazones of the formula (IV)
in which
G, R and Z have the abovementioned meanings,
are reacted with an aldehyde of the general formula (III), optionally in the presence of a diluent and optionally in the presence of a catalyst, or by a process in which
c) hydrazine derivatives of the formula (V)
in which
L
1
, L
2
, L
3
and L
4
have the abovementioned meanings,
are reacted with a ketone of the general formula (II), optionally in the presence of a diluent and optionally in the presence of a catalyst.
Finally, it has been found that the new azines of the general formula (I) show a very potent fungicidal action.
Where appropriate, the compounds according to the invention can be in the form of mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z isomers or optical isomers. Both the E and the Z isomers, the individual enantiomers, the racemates and also any desired mixtures of these isomers are claimed.
Preferred azines of the formula (I) are those in which
G represents a single bond,
R represents alkyl having 1 to 4 carbon atoms, or cycloalkyl which has 3 to 6 carbon atoms and is optionally mono- to tetrasubstituted by halogen or alkyl,
Z
represents cycloalkyl or cycloalkylalkyl which has in each case 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part and is in each case optionally monosubstituted to tetrasubstituted by halogen or alkyl;
represents heterocyclyl or heterocyclylalkyl which has in each case 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl part and is optionally substituted by halogen or alkyl having 1 to 4 carbon atoms;
or represents aryl or arylalkyl which has in each case 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part and is in each case optionally monosubstituted to tetrasubstituted in the aryl part in an identical or different manner, the possible substituents preferably being chosen from the following list:
halogen, cyano, nitro, amino, formyl, 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, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, alkenylcarbonyl or alkinylcarbonyl having 1 to 6 carbon atoms in the particular hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms; in each case divalent alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, in each case optionally monosubstituted to tetrasubstituted in an identical or different manner by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl;
or a grouping
wherein
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 or dialkylamino having 1 to 4 carbon atoms in the particular alkyl chains and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another in each case represent hydrogen, halogen, cyano, nitro or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and in each case optionally substituted by 1 to 5 halogen atoms, preferably hydrogen or methyl, and in particular hydrogen.
Azines of the formula (I) which are likewise preferred are those in which
G represents a grouping
wherein
R
1
represents hydrogen, or represents alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkinyl having 2 to 6 carbon atoms, in each case optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms, or represents cycloalkyl which has 3 to 8 carbon atoms and is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms, or represents arylalkyl which has 1 to 4 carbon atoms in the alkyl part and is optionally substituted in the aryl part, the substituents being chosen from the following list:
halogen, cyano, nitro, formyl, 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 ea
Gayer Herbert
Hänssler Gerd
Hillebrand Stefan
Krüger Bernd-Wieland
Mauler-Machnik Astrid
Bayer Aktiengesellschaft
Gil Joseph C.
Habte Kahsay
Harmuth Raymond J.
Raymond Richard L
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