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US 5,593,945 AGranted
N-cyanoaryl-nitrogen heterocycles
AssigneeBayer Aktiengesellschaft
InventorsRoland Andree, Mark-Wilhelm Drewes, Albrecht Marhold, Hans-Joachim Santel, Markus Dollinger
Life of this patent
Estimating the term…
Abstract
The invention relates to new N-cyanoaryl-nitrogen heterocycles of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Z have the meanings given in the description, to a plurality of processes for their preparation, to their use as herbicides and to novel intermediates.
Claims26
A N-cyanoaryl-nitrogen heterocycle of the formula ##STR887## wherein R.sup.2 is fluorine, chlorine, bromine, cyano, amino or the group --N(A.sup.1)SO.sub.2 A in which
- A is a radical selected from the group consisting of alkyl, alkenyl and alkinyl, each of which has up to 10 carbon atoms and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxy, or
- A is cycloalkyl or cycloalkylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkyl, or
- A is aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by dimethylaminosulphonyl or diethylaminosulphonyl, by C.sub.1 -C.sub.4 -alkoxycarbonyl (which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy), by phenyl, phenyloxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy), or
- A is thienyl, pyrazolyl or pyridyl, or thienyl-pyrazolyl- or pyridyl-alkyl having 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by phenyl, phenoxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- A.sup.1 is hydrogen or alkyl, alkenyl, alkinyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each of which has up to 6 carbon atoms and each of which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or is phenylcarbonyl, naphthylcarbonyl, phenylmethylcarbonyl, naphthylmethylcarbonyl, phenoxycarbonyl or napthyloxycarbonyl (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- R.sup.3 is hydrogen, fluorine, chlorine, bromine, cyano or alkyl having 1 to 6 carbon atoms which is optionally substituted by at least one of fluorine and/or chlorine,
- R.sup.4 is alkyl having 1 to 6 carbon atoms which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy,
- or together with R.sup.3 is alkanediyl having 2 to 8 carbon atoms, and
- Z is ##STR888## or a salt thereof with a base.
6 more elements
A N-cyanoaryl-nitrogen heterocycle of the formula ##STR893## wherein R.sup.1 is hydrogen, fluorine, chlorine or bromine,
- R.sup.2 is fluorine, chlorine, bromine, cyano, amino or the group --N(A.sup.1)SO.sub.2 A in which
- A is a radical selected from the group consisting of alkyl, alkenyl and alkinyl, each of which has up to 10 carbon atoms and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxy, or
- A is cycloalkyl or cycloalkylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkyl, or
- A is aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by dimethylaminosulphonyl or diethylaminosulphonyl, by C.sub.1 -C.sub.4 -alkoxy carbonyl (which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy), by phenyl, phenyloxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy), or
- A is thienyl, pyrazolyl or pyridyl, or thienyl-, pyrazolyl- or pyridyl-alkyl having 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by phenyl, phenoxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- A.sup.1 is hydrogen or alkyl, alkenyl, alkinyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each of which has up to 6 carbon atoms and each of which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or is phenylcarbonyl, naphthylcarbonyl, phenylmethylcarbonyl, naphthylmethylcarbonyl, phenoxycarbonyl or napthyloxycarbonyl (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- R.sup.3 is hydrogen, fluorine, chlorine, bromine, cyano or alkyl having 1 to 6 carbon atoms which is optionally substituted by at least one of fluorine and chlorine,
- R.sup.4 is alkyl having 1 to 6 carbon atoms which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, or together with R.sup.3 is alkanediyl having 2 to 8 carbon atoms,
- or a salt thereof with a base.
6 more elements
A N-cyanoaryl-nitrogen heterocycle of the formula ##STR894## wherein R.sup.2 is fluorine, chlorine, bromine, cyano, amino or the group --N(A.sup.1)SO.sub.2 A in which
- A is a radical selected from the group consisting of alkyl, alkenyl and alkinyl, each of which has up to 10 carbon atoms and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkoxy, or
- A is cycloalkyl or cycloalkylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C.sub.1 -C.sub.4 -alkyl, or
- A is aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by dimethylaminosulphonyl or diethylaminosulphonyl, by C.sub.1 -C.sub.4 -alkoxy carbonyl (which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy), by phenyl, phenyloxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy), or
- A is thienyl, pyrazolyl or pyridyl, or thienyl-, pyrazolyl- or pyridyl-alkyl having 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl (each of which is optionally substituted by at least one of fluorine and chlorine), by phenyl, phenoxy or phenylthio (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- A.sup.1 is hydrogen or alkyl, alkenyl, alkinyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each of which has up to 6 carbon atoms and each of which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or is phenylcarbonyl, naphthylcarbonyl, phenylmethylcarbonyl, naphthylmethylcarbonyl, phenoxycarbonyl or napthyloxycarbonyl (each of which is optionally substituted by at least one of fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and trifluoromethoxy),
- R.sup.3 is hydrogen, fluorine, chlorine, bromine, cyano or alkyl having 1 to 6 carbon atoms which is optionally substituted by at least one of fluorine and chlorine,
- R.sup.4 is alkyl having 1 to 6 carbon atoms which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, or together with R.sup.3 is alkanediyl having 2 to 8 carbon atoms,
- or a salt thereof with a base.
5 more elements
Dependencies are inferred from the claim text.