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US 5,393,729 AGranted
3-aryl-pyrone derivatives
AssigneeBayer Aktiengesellschaft
InventorsReiner Fischer, Andreas Krebs, Folker Lieb, Michael Ruther, Jorg Stetter, Christoph Erdelen, Ulrike Wachendorff-Neumann, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
Life of this patent
Estimating the term…
Abstract
The invention relates to 3-aryl-pyrone derivatives of the general formula (I) ##STR1## in which the substituents are as defined in the specification. The compounds are useful as pesticides, herbicides and fungicides.
Claims10
A 3-aryl-pyrone of the formula ##STR44## in which A represents hydrogen;
- halogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -alkinyl and C.sub.3 -C.sub.10 -cycloalkyl, each of which is optionally substituted by halogen;
- a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl, each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -halogenoalkoxy and CN;
- or represents the group --COR.sup.1, --CO.sub.2 R.sup.1, --CN, --CONR.sup.1 R.sup.2, --SO.sub.2 R.sup.1 or --P(O)(OR.sup.1)(OR.sup.2), in which
- R.sup.1 and R.sup.2 independently of one another represent hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl and C.sub.3 -C.sub.10 -alkenyl, each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl, each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -halogenoalkoxy and CN;
- or R.sup.1 and R.sup.2 together represent a C.sub.2 -C.sub.7 -alkylene group which is optionally interrupted by nitrogen, oxygen or sulphur;
- B represents hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -alkinyl and C.sub.3 -C.sub.10 -cycloalkyl which are optionally substituted by halogen, CN, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylcarbonyloxy or phenyl;
- or represents a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl which are optionally substituted by at least one of halogen, CN, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl and C.sub.1 -C.sub.8 -halogenoalkoxy, or
- A and B together represent a straight chain or branched C.sub.2 -C.sub.7 -alkylene group which is optionally substituted by at least one of C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio and halogen and which is optionally interrupted by nitrogen, sulphur, oxygen or --O--CO--;
- X represents halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy;
- Y represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -halogenoalkyl;
- Z represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy;
- n represents 1 or 2;
- G represents hydrogen, --COR.sup.3, ##STR45## R.sup.3 represents a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkylthio-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -polyalkoxy-C.sub.1 -C.sub.8 -alkyl and C.sub.3 -C.sub.8 -cycloalkyl which is optionally interrupted by at least one of oxygen and sulphur, each of these radicals optionally being substituted by halogen;
- phenyl which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkyl and C.sub.1 -C.sub.6 -halogenoalkoxy;
- phenyl-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkyl and C.sub.1 -C.sub.6 -halogenoalkoxy;
- hetaryl which is optionally substituted by at least one of halogen and C.sub.1 -C.sub.6 -alkyl;
- phenoxy-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen and C.sub. 1 -C.sub.6 -alkyl;
- or hetaryloxy-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen, amino and C.sub.1 -C.sub.6 -alkyl;
- R.sup.4 represents a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl and C.sub.1 -C.sub.8 -polyalkoxy-C.sub.1 -C.sub.8 -alkyl each of which is optionally substituted by halogen;
- or a radical selected from the group consisting of phenyl and benzyl each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -halogenoalkyl;
- R.sup.5, R.sup.6 and R.sup.7 independently of one another represent a radical selected from the group consisting of C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylamino, di-(C.sub.1 -C.sub.8)-alkylamino, C.sub.2 -C.sub.5 -alkenylthio, C.sub.2 -C.sub.5 -alkinylthio and C.sub.3 -C.sub.7 -cycloalkylthio each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl, phenyloxy and phenylthio, each of which is optionally substituted by at least one of halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.1 -halogenoalkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -halogenoalkylthio, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -halogenoalkyl;
- R.sup.8 and R.sup.9 independently of one another represent hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.2 -C.sub.8 -alkenyl and C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl and benzyl each of which is optionally substituted by at least one of halogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -halogenoalkyl and C.sub.1 -C.sub.20 -alkoxy;
- or R.sup.8 and R.sup.9 together form a C.sub.2 -C.sub.6 -alkylene group which is optionally interrupted by at least one of oxygen and sulphur;
- L represents oxygen or sulphur and
- M represents oxygen or sulphur,
- with the exception of the compound 2,4-pentadienoic acid, 3,5-dihydroxy-2-(o-methoxyphenyl)-5-phenyl-.delta.-lactone.
30 more elements
A method of combating anthropods, nematodes, parasites or undesired vegetation which comprises applying thereto or to a locus from which it is desired they be excluded an amount effective therefor of a 3-aryl-pyrone of the formula ##STR51## in which A represents hydrogen;
- halogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -alkinyl and C.sub.3 -C.sub.10 -cycloalkyl, each of which is optionally substituted by halogen;
- a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl, each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -halogenoalkoxy and CN;
- or represents the group --COR.sup.1, --CO.sub.2 R.sup.1, --CN, --CONR.sup.1 R.sup.2, --SO.sub.2 R.sup.1 or --P(O)(OR.sup.1)(OR.sup.2), in which R.sup.1 and R.sup.2 independently of one another represent hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl and C.sub.3 -C.sub.10 -alkenyl, each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl, each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -halogenoalkoxy and CN;
- or R.sup.1 and R.sup.2 together represent a C.sub.2 -C.sub.7 -alkylene group which is optionally interrupted by nitrogen, oxygen or sulphur;
- B represents hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -alkinyl and C.sub.3 -C.sub.10 -cycloalkyl which are optionally substituted by halogen, CN, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylcarbonyloxy or phenyl;
- or represents a radical selected from the group consisting of phenyl, naphthyl, hetaryl, phenyl-C.sub.1 -C.sub.6 -alkyl and hetaryl-C.sub.1 -C.sub.6 -alkyl which are optionally substituted by at least one of halogen, CN, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkyl and C.sub.1 -C.sub.8 -halogenoalkoxy, or
- A and B together represent a straight chain or branched C.sub.2 -C.sub.7 -alkylene group which is optionally substituted by at least one of C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio and halogen and which is optionally interrupted by nitrogen, sulphur, oxygen or --O--CO--;
- X represents halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy;
- Y represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -halogenoalkyl;
- Z represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy;
- n represents 1 or 2;
- G represents hydrogen, --COR.sup.3, ##STR52## R.sup.3 represents a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkylthio-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -polyalkoxy-C.sub.1 -C.sub.8 -alkyl and C.sub.3 -C.sub.8 -cycloalkyl which is optionally interrupted by at least one of oxygen and sulphur, each of these radicals optionally being substituted by halogen;
- phenyl which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkyl and C.sub.1 -C.sub.6 -halogenoalkoxy;
- phenyl-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkyl and C.sub.1 -C.sub.6 -halogenoalkoxy;
- hetaryl which is optionally substituted by at least one of halogen and C.sub.1 -C.sub.6 -alkyl;
- phenoxy-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen and C.sub. 1 -C.sub.6 -alkyl;
- or hetaryloxy-C.sub.1 -C.sub.6 -alkyl which is optionally substituted by at least one of halogen, amino and C.sub.1 -C.sub.6 -alkyl;
- R.sup.4 represents a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl and C.sub.1 -C.sub.8 -polyalkoxy-C.sub.1 -C.sub.8 -alkyl each of which is optionally substituted by halogen;
- or a radical selected from the group consisting of phenyl and benzyl each of which is optionally substituted by at least one of halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -halogenoalkyl;
- R.sup.5, R.sup.6 and R.sup.7 independently of one another represent a radical selected from the group consisting of C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylamino, di-(C.sub.1 -C.sub.8)-alkylamino, C.sub.2 -C.sub.5 -alkenylthio, C.sub.2 -C.sub.5 -alkinylthio and C.sub.3 -C.sub.7 -cycloalkylthio each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl, phenyloxy and phenylthio, each of which is optionally substituted by at least one of halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -halogenoalkylthio, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -halogenoalkyl;
- R.sup.8 and R.sup.9 independently of one another represent hydrogen;
- a radical selected from the group consisting of C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.2 -C.sub.8 -alkenyl and C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl each of which is optionally substituted by halogen;
- or represent a radical selected from the group consisting of phenyl and benzyl each of which is optionally substituted by at least one of halogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -halogenoalkyl and C.sub.1 -C.sub.20 -alkoxy;
- or R.sup.8 and R.sup.9 together form a C.sub.2 -C.sub.6 -alkylene group which is optionally interrupted by at least one of oxygen and sulphur;
- L represents oxygen or sulphur and
- M represents oxygen or sulphur.
28 more elements
Dependencies are inferred from the claim text.