Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-09-05
2002-10-08
Rao, Deepak R. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000
Reexamination Certificate
active
06462039
ABSTRACT:
The invention relates to novel benzoheterocyclyloximes, 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, WO 95-04 728, WO 96-25 406, WO 97-07 103). However, the fungicidal activity of these compounds is, in particular at low application rates, unsatisfactory.
This invention, accordingly, provides the novel benzoheterocyclyloximes of the general formula (I)
in which
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represent hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
R represents alkyl or optionally substituted cycloalkyl having 3 to 5 carbon atoms,
X
1
and X
2
independently of one another represent hydrogen or halogen and
Z represents optionally substituted benzoheterocyclyl which is attached via the heterocyclyl moiety.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched, even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, 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 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 or sulphur.
Benzoheterocyclyl represents a heterocyclic ring having a fused-on benzene ring.
Furthermore, it has been found that the novel benzoheterocyclyloximes of the general formula (I) are obtained when oximes of the general formula (II)
in which
R and Z are as defined above,
are reacted with a halogenomethyl compound of the general formula (III)
in which
L
1
, L
2
, L
3
, L
4
, X
1
and X
2
are as defined above and
Y represents halogen,
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 benzoheterocyclyloximes of the general formula (I) have very strong fungicidal activity.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereolsomers, 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 benzoheterocyclyloximes of the formula (Ia), in which
E represents oxygen, sulphur, NH, or N-R
5
, where
R
5
represents alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, where the hydrocarbon groups are in each case optionally substituted by 1 to 5 halogen atoms, or represents benzyl which is optionally mono- to pentasubstituted by halogen, cyano, nitro, alkyl or alkoxy having 1 to 4 carbon atoms, halogenoalkyl or halogenoalkyloxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms,
G represents nitrogen or CH,
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, represents alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case optionally substituted by 1 to 5 halogen atoms, preferably represents hydrogen or methyl and in particular represents hydrogen,
X
1
and X
2
independently of one another represent hydrogen, fluorine or chlorine, in particular hydrogen,
R represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms and being optionally mono- to tetrasubstituted by halogen or alkyl, preferably represents methyl or cyclopropyl, in particular represents methyl,
R
1
, R
2
, R
3
and R
4
are identical or different and independently of one another each represents
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 or 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 respective carbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
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, or
R
1
and R
2
, or R
2
and R
3
, or R
3
and R
4
together represent 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 fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl.
Particular preference is given to benzoheterocyclyloximes of the formula (Ia), in which
E represents oxygen, sulphur, NH, or N-R
5
, where
R
5
represents methyl, ethyl, n- or i-propyl, fluoromethyl, difluoromethyl, allyl, propargyl, benzyl or 4-chlorobenzyl,
G represents nitrogen or CH,
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, fluorine, chlorine, methyl or methoxy, preferably represents hydrogen or methyl and in particular represents hydrogen,
X
1
and X
2
independently of one another represent hydrogen or fluorine, in particular represent hydrogen,
R represents methyl, ethyl, n- or i-propyl, or represents cyclopropyl, cyclobutyl or cyclopentyl, each of which is optionally mono- to tetrasubstituted by fluorine, chlorine, methyl or ethyl, in particular represents methyl,
R
1
, R
2
, R
3
and R
4
are identical or different and independently of one another each represents
fluorine, chlorine, bromine, cyano, nitro, amino, fonnyl, carbamoyl, thiocarbamoyl,
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxymethyl,
methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
methylaminomethyl, dimethylaminomethyl,
vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
trifluoromethyl, trifluoroethyl,
difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl,
methylamino, ethylamino, n- or i-propylamino, dimetlhylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, dimethylaminocarbonyl, acryloyl, propioloyl,
cyclopentyl, cyclohexyl,
or a grouping
in which
A
1
represents hydrog
Gayer Herbert
Gerdes Peter
Hänssler Gerd
Hillebrand Stefan
Krüger Bernd-Wieland
Bayer Aktiengesellschaft
Gil Joseph C.
Rao Deepak R.
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