Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-10-30
2002-06-18
Ford, John M. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S002000
Reexamination Certificate
active
06407097
ABSTRACT:
The invention relates to novel methoximinomethyloxathiazines, to two processes for their preparation and to their use as pesticides.
Certain methoximinomethyloxathiazines having a similar substitution pattern, and their fungicidal action, have already been disclosed (WO 96-25406). However, the action of these prior-art compounds is, in particular at low application rates and concentrations, not entirely satisfactory in all areas of use.
This invention, accordingly, provides the novel methoximinomethyloxathiazines of the general formula (I)
in which
Z represents in each case optionally substituted cycloalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
Q represents oxygen or sulphur,
X represents halogen and
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.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as, for example, an alkoxy, alkylthio or alkylamino.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, by way of example and preferably, 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 other than carbon. If the ring contains a plurality of heteroatoms, these may be identical or different. Preferred heteroatoms 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 annular compounds which, if appropriate, form a polycyclic ring system with other carbocyclic fused-on or bridged rings.
Furthermore, it has been found that the novel methoximinomethyloxathiazines of the general formula (I) are obtained when
a) 3-(2-hydroxyphenyl)-3-methoxyiminomethyl-oxathiazines of the formula (II)
in which
L
1
, L
2
, L
3
and L
4
are each as defined above,
are reacted with a substituted halogenopyrimidine of the general formula (III)
in which
Z, Q and X are each as defined above and
Y
1
represents halogen,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst, or when
b) phenoxypyrimidines of the general formula (IV)
in which
X, L
1
, L
2
, L
3
and L
4
are each as defined above an
Y
2
are presents halogen
are reacted with a cyclic compound of the general formula (V)
Z—Q—H (V)
in which
Z and Q are each as defined above,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel methoximinomethyloxathiazines of the general formula (I) have very strong microbicidal action.
If appropriate, the compounds according to the invention can be present as mixtures of various possible isomeric forms, in particular of steroisomers, such as, for example, E and Z. What is claimed are both the E and the Z isomers, and any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
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, each of which is optionally mono- or disubstituted by halogen or alkyl;
represents heterocyclyl or heterocyclylalkyl having in each case 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by halogen or alkyl having 1 to 4 carbon atoms;
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, each of which is 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, formyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkyl sulphonyl 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 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 selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
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,
Q represents oxygen or sulphur,
X represents fluorine, chlorine or bromine, preferably fluorine or chlorine and in particular fluorine 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, 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 hydrogen.
The invention relates in particular to compounds of the formula (I) in which
Z represents cyclopentyl or cyclohexyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;
represents thienyl, pyridyl, furyl, thienylmethyl, pyridylmethyl or furylmethyl, each of which is optionally substituted by methyl, ethyl, fluorine, chlorine or bromine;
or, in particular, represents phenyl or benzyl, each of which is optionally mono- to tetrasubstituted, in particular mono- or disubstituted, by identical or different substituents, where the possible substituents are preferably selected from the list below:
fluorine, chlorine, bromine, cyano, nitro, amino, formyl, 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, propene-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propene-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
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Krüger Bernd-Wieland
Stenzel Klaus
Bayer Aktiengesellschaft
Ford John M.
Gil Joseph C.
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