Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2001-01-02
2002-02-26
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C514S327000, C514S331000, C514S345000, C514S352000, C514S360000, C514S367000, C514S385000, C514S393000, C514S412000, C514S438000, C514S443000, C514S445000, C514S456000, C514S461000, C514S473000, C514S616000, C546S216000, C546S229000, C546S290000, C546S329000, C548S124000, C548S146000, C548S152000, C548S302700, C549S049000, C549S051000, C549S065000, C549S076000, C549S462000, C549S475000, C549S491000, C564S142000, C564S144000
Reexamination Certificate
active
06350909
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to new imides, to a plurality of processes for their preparation, and to their use as fungicides.
BACKGROUND OF THE INVENTION
It is known that certain imides which are similar to those mentioned below have fungicidal properties (cf., for example, EP-A 398692, EP-A 528681 and WO 97-00856). However, the action of these compounds is not entirely satisfactory in all fields of application, in particular when low application rates are used.
SUMMARY OF THE INVENTION
Novel imides have general formula (1)
in which
X represents halogen or alkoxy and
Z represents optionally substituted aryl or a group
in which
R
1
represents optionally substituted alkyl, cycloalkyl or arylalkyl,
R
2
represents optionally substituted alkyl, aryl, cycloalkyl, arylalkyl, heterocyclyl or heterocyclylalkyl,
Z
1
represents a single bond, oxygen, sulphur or a group
where
R
4
represents alkyl, or together with R
2
and the nitrogen atom to which they are bonded forms an optionally substituted heterocyclic ring. 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.
Furthermore, it has been found that the new substituted heterocycloalkenes of the general formula (I) are obtained when
carboxamides of the general formula (II)
in which
Z is as defined above,
are reacted with an carbonyl halide of the formula (III),
in which
X is as defined above, and
X
1
represents halogen, or
are reacted with a carboxylic anhydride of the formula (IV)
in which
X is as defined above,
in each case if appropriate in the presence of a diluent and in each case if appropriate in the presence of an acid binder.
Finally, it has been found that the new carboxamide derivatives of the general formula (I) have a very potent fungicidal action.
If appropriate, the compounds according to the invention may exist as mixtures of various isomeric forms which are possible, in particular stereoisomers such as for example, E- and Z-isomers but, if appropriate, also in the form of tautomers. Claimed are the E- and the Z-isomers, any mixtures of these isomers, and the tautomeric forms which are possible.
The present invention preferably relates to imides of the formula (I) in which
X represents chlorine or alkoxy having 1 to 4 carbon atoms and
Z represents phenyl or naphthyl, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, the substituents which are possible preferably being selected from the list hereinbelow:
halogen, cyano, nitro, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which have 1 to 6 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 alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulphonyloxy, each of which has 1 to 6 carbon atoms in the individual alkyl moieties;
in each case divalent alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms and each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the series consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
cycloalkyl having 3 to 6 carbon atoms;
heterocyclyl or heterocyclyl-methyl, each of which has 3 to 7 ring members of which in each case 1 to 3 are identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur;
or a group
in which
A
1
represents alkyl with 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl, each of which has 2 to 4 carbon atoms, optionally substituted by cyano, alkoxy, alkylthio, alkylamino, dial kylamino or phenyl,
Z also represents a group
in which
R
1
represents alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen or alkyl having 1 to 4 carbon atoms, or arylalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, and which is optionally substituted in the aryl moiety, the substituents preferably being selected from the following list:
halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 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;
R
2
represents alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen or alkyl having 1 to 4 carbon atoms,
or represents heterocyclyl, benzoheterocyclyl, dibenzoheterocyclyl or heterocyclylalkyl, each of which has 3 to 7 ring members in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkyl moiety and 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 represents aryl or arylalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted in the aryl moiety, the substituents preferably being selected from the following list:
halogen, cyano, nitro, amino, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, 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, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or arylalkylaminocarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy, each of which has 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 by identical or different substituents from the series consisting of fluorine, chlorine, methyl, trifluoromethyl or ethyl;
phenoxy or phenylalkoxy having 1 to 4 carbon atoms in the alkyl moiety and in each case 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
Gayer Herbert
Gerdes Peter
Hänssler Gerd
Heinemann Ulrich
Jaetsch Thomas
Bayer Aktiengesellschaft
Gil Joseph C.
Kumar Shailendra
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