Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2000-04-27
2002-06-18
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
Reexamination Certificate
active
06407233
ABSTRACT:
The invention relates to new halogenopyrimidines, to a process for their preparation, and to their use as pesticides.
Certain pyrimidines which have a similar substitution pattern have already been disclosed (WO-A 9504728).
However, the activity of these prior-art compounds is not entirely satisfactory in all fields of application, in particular when low rates and concentrations are applied.
There have now been found the new halogenopyrimidines of the general formula (I)
in which
A represents optionally substituted alkanediyl,
R represents in each case optionally substituted cycloalkyl, aryl or benzo-fused heterocyclyl,
E represents —CH═ or nitrogen,
Q represents oxygen, sulphur, —CH
2
—O—, a single bond, or a nitrogen atom which is optionally substituted by alkyl, and
X represents halogen
Furthermore, it has been found that the new halogenopyrimidines of the general formula (I) are obtained when
a) hydroxy compounds of the general formula (II)
in which
A and E have the abovementioned meanings, are reacted with a substituted halogenopyrimidine of the general formula (III)
in which
R, Q and X have the abovementioned meanings 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
A, E and X have the abovementioned meanings and
Y
2
represents halogen are reacted with a cyclic compound of the general formula (V)
R—Q—H (V)
in which
R and Q have the abovementioned meanings, 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 new halogenopyrimidines of the general formula (I) have a very powerful fungicidal activity.
Where appropriate, the compounds according to the invention can exist in the form of mixtures of various isomeric forms which are possible, in particular of stereoisomers, such as, for example, E and Z isomers. Claimed are not only the E and the Z isomers, but also any mixtures of these isomers.
The invention preferably relates to compounds of the formula (I) in which
A represents alkanediyl having 1 to 5 carbon atoms which is optionally substituted by halogen,
R represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally monosubstituted to disubstituted by halogen, alkyl or hydroxyl;
or represents benzodioxanyl which is optionally substituted by alkyl having 1 to 4 carbon atoms;
or represents phenyl or naphthyl, each of which is optionally monosubstituted to tetrasubstituted by identical or different substituents, other substituents which are possible preferably being selected from amongst the enumeration which follows:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thio-carbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms,
in each case straight-chain or branched alkenyl or alkenyloxy, each of which has 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each of which has 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy, each of which has 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl or alkinylcarbonyl, each of which has 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy, each of which has 3 to 6 carbon atoms;
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 by identical or different substituents from the series consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl;
or a group
where
A
1
represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, phenyl, benzyl, or represents alkyl or alkoxy having 1 to 4 carbon atoms, each of which is optionally substituted by cyano, hydroxyl, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl, or represents alkenyloxy or alkinyloxy, each of which has 2 to 4 carbon atoms,
and also phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl, phenylalkyl, phenylalkyloxy, phenylalkylthio or heterocyclylalkyl, each of which has 1 to 3 carbon atoms in the respective alkyl moieties and each of which is optionally monosubstituted to trisubstituted in the cyclic moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms,
E represents —CH═ or nitrogen,
Q represents oxygen, sulphur, a single bond or a nitrogen atom which is optionally substituted by methyl, ethyl or n- or i-propyl and
X represents fluorine, chlorine, bromine or iodine.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, also together with hetero atoms, such as, for example, in alkoxy, alkylthio or alkylamino, are in each case straight-chain or branched.
In particular, the invention relates to compounds of the formula (I) in which
A represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl or butane-2,2-diyl, each of which is optionally substituted by fluorine or chlorine,
R represents cyclopentyl or cyclohexyl, each of which is optionally monosubstituted to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;
or represents benzodioxanyl which is optionally substituted by methyl or ethyl;
or represents phenyl or naphthyl, each of which is optionally monosubstituted to tetrasubstituted by identical or different substituents the substituents which are possible preferably being selected from amongst the enumeration which follows:
fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl,
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,
methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
trifluoromethyl, trifluoroethyl,
difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl,
methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino,
acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxey, diethylaminocarbonyloxy, benzylaminocarbonyl, acryloyl, propioloyl,
cyclopentyl, cyclohexyl,
in each case divalent propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy, each of which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of fluorine, chlorine, oxo, methyl or trifluoromethyl,
or a group
where
A
1
represents hydrogen, methyl or hydroxyl and
A
2
represents hydroxyl, m
Dutzmann Stefan
Gallenkamp Bernd
Gayer Herbert
Gerdes Peter
Hänssler Gerd
Bayer Aktiengesellschaft
Norris & McLaughlin & Marcus
Patel Sudhaker B.
Shah Mukund J.
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