# US 5,350,861 A · Substituted 3-aryl-pyrrolidine-2,4-diones

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- Number: US 5,350,861 A
- Document ID: US5350861A
- Status: Granted
- Kind: A
- Application number: 07/821,801
- Filed: 1992-01-16
- Granted: 1994-09-27
- Earliest claimed: 1991-01-26
- Assignees: Bayer Aktiengesellschaft
- Inventors: Reiner Fischer; Hermann Uhr; Arno Widdig; Stefan Dutzmann; Christoph Erdelen; Ulrike Wachendorff-Neumann; Klaus Schaller
- Web page: https://patentgrep.com/patent/US5350861A

## CPC

- A01N 43/36: five-membered rings
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- C07D 207/38: 2-Pyrrolones
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

There are provided new substituted 3-aryl-pyrrolidine-2,4-diones of the formula ##STR1## in which X represents hydrogen, alkyl, halogen or alkoxy, Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl, Z represents alkyl, halogen or alkoxy, n represents a number from 0-3, R represents hydrogen or the groups --CO--R.sup.1, --CO--O--R.sup.2 in which R.sup.1 and R.sup.2 have the meanings given in the text of the application, A represents optionally halogen-substituted alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl and cycloalkyl which is optionally interrupted by hetero atoms, or represents arylakyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or nitro, B represents optionally substituted aryl or benzyl. The new compounds of the formula (I) have highly pronounced insecticidal, acaricidal, fungicidal and antimycotic properties.

## Claims

### Claim 1

Substituted 3-aryl-4-hydroxy-2-ones of the formula (I) ##STR352## in which X represents hydrogen, C.sub.1-6 -alkyl, halogen or C.sub.1-6 -alkoxy,
Y represents hydrogen, C.sub.1-6 -alkyl, halogen, C.sub.1-6 -alkoxy or C.sub.1-3 -halogenoalkyl,
Z represents C.sub.1-6 -alkyl, halogen or C.sub.1-6 -alkoxy,
n represents a number from 0-3,
R represents hydrogen (Ia) or the groups of the formula
--CO--R.sup.1 (Ib)
or
--CO--O--R.sup.2 (Ic)
in which
R.sup.1 represents optionally halogen-substituted C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.1-8 -alkoxy-C.sub.2-8 -alkyl, C.sub.1-8 -alkylthio-C.sub.2-8 -alkyl, C.sub.1-8 -polyalkoxy-C.sub.2-8 -alkyl or cycloalkyl which has 3-8 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms,
or represents phenyl which is optionally substituted by halogen, nitro, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -halogenoalkyl or C.sub.1-6 -halogenolakoxy,
or represents phenyl-C.sub.1-6 -alkyl which is optionally substituted by halogen, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -halogenoalkyl or C.sub.1-6 -halogenoalkoxy,
or represents phenoxy-C.sub.1-6 -alkyl which is optionally substituted by halogen or C.sub.1-6 -alkyl,
R.sup.2 represents optionally halogen-substituted C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.1-16 -alkoxy-C.sub.2-6 -alkyl or C.sub.1-8 -polyalkoxy-C.sub.2-8 -alkyl,
or represents phenyl which is optionally substituted by halogen, nitro, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy or C.sub.1-6 -halogenoalkyl,
A represents optionally halogen-substituted straight-chain or branched C.sub.1-12 -alkyl, C.sub.3-8 -alkenyl, C.sub.3-8 -alkinyl, C.sub.1-10 -alkoxy-C.sub.2-8 -alkyl, C.sub.1-8 -polyalkoxy-C.sub.2-8 -alkyl, C.sub.1-10 -alkylthio-C.sub.2-8 -alkyl, cycloalkyl which has 3-8 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms, or represents aryl-C.sub.1-6 -alkyl which is optionally substituted by halogen, C.sub.1-6 -alkyl, C.sub.1-6 -halogenoalkyl, C.sub.1-6 -alkoxy or nitro,
B represents phenyl or benzyl which are optionally monosubstituted or disubstituted by identical or different substituents selected from the group consisting of nitro, halogen, or in each case optionally halogen-substituted C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy,
and the pure enantiomeric forms of compounds of the formula (I).

### Claim 2 (depends on 1)

Substituted 3-aryl-4-hydroxy-pyrrolidin-2-ones of the formula (I) according to claim 1, in which
X represents hydrogen, methyl, ethyl, propyl, i-propyl, fluorine, chlorine, bromine, methoxy and ethoxy,
Y represents hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, tert.-butyl, fluorine, chlorine, bromine, methoxy, ethoxy and trifluoromethyl,
Z represents methyl, ethyl, i-propyl, butyl, i-butyl, tert.-butyl, fluorine, chlorine, bromine, methoxy and ethoxy,
n represents a number from 0-3,
R represents hydrogen (Ia) or the groups of the formula
--CO--R.sup.1 (Ib)
or
--CO--O--R.sup.2 (Ic)
in which
R.sup.1 represents optionally fluorine- or chlorine-substituted C.sub.1 -C.sub.14 -alkyl, C.sub.2 -C.sub.14 -alkenyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.2 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -polyalkoxy-C.sub.2 -C.sub.4 -alkyl and cycloalkyl which has 3-6 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms,
or represents phenyl which is optionally substituted bu fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or nitro,
or represents phenyl-C.sub.1 -C.sub.3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
or represents phenoxy-C.sub.1 -C.sub.4 -alkyl which is optionally substituted by fluorine, chlorine, methyl or ethyl,
R.sup.2 represents optionally fluorine- or chlorine-substituted C.sub.1 -C.sub.14 -alkyl, C.sub.2 -C.sub.14 -alkenyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -polyalkoxy-C.sub.2 -C.sub.6 -alkyl,
or represents phenyl which is optionally substituted by fluorine, chlorine, nitro, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy or trifluoromethyl,
A represents optionally halogen-substituted straight-chain or branched C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.4 -alkenyl, C.sub.3 -C.sub.4 -alkinyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -polyalkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.2 -C.sub.4 -alkyl or cycloalkyl which has 3-6 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms, or represents aryl-C.sub.1 -C.sub.3 -alkyl which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl or nitro,
B represents unsubstituted phenyl or benzyl, or represents phenyl or benzyl which are substituted by nitro, fluorine, chlorine or optionally fluorine- or chlorine-substituted C.sub.1 -C.sub.2 -alkyl or C.sub.1 -C.sub.2 -alkoxy,
and the pure enantiomeric forms of compounds of the formula I.

### Claim 3 (depends on 1)

Substituted 3-aryl-4-hydroxy-pyrrolidin-2-ones of the formula (I) according to claim 1, in which
X represents hydrogen, C.sub.1-4 -alkyl, halogen or C.sub.1-6 -alkoxy,
Y represents hydrogen, C.sub.1-6 -alkyl, halogen, C.sub.1-4 -alkoxy or C.sub.1-2 -halogenoalkyl,
Z represents C.sub.1-4 -alkyl, halogen or C.sub.1-4 -alkoxy,
n represents a number from 0-3,
R represents hydrogen (Ia) or the groups of the formula
--CO--R.sup.1 (Ib)
or
--CO--O--R.sup.2 (Ic)
in which
R.sup.1 represents optionally halogen-substituted C.sub.1-16 -alkyl, C.sub.2-16 -alkenyl, C.sub.1-6 -alkoxy-C.sub.2-6 -alkyl, C.sub.1-6 -alkylthio-C.sub.2-6 -alkyl, C.sub.1-6 -polyalkoxy-C.sub.2-6 -alkyl or cycloalkyl which has 3-7 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms,
or represents phenyl which is optionally substituted by halogen, nitro, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-3 -halogenoalkyl or C.sub.1-3 -halogenolakoxy,
or represents phenyl-C.sub.1-4 -alkyl which is optionally substituted by halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-3 -halogenoalkyl or C.sub.1-3 -halogenoalkoxy,
or represents phenoxy-C.sub.1-5 -alkyl which is optionally substituted by halogen or C.sub.1-4 -alkyl,
R.sup.2 represents optionally halogen-substituted C.sub.1-16 -alkyl, C.sub.2-16 -alkenyl, C.sub.1-16 -alkoxy-C.sub.2-6 -alkyl or C.sub.1-6 -polyalkoxy-C.sub.2-6 -alkyl,
or represents phenyl which is optionally substituted by halogen, nitro, C.sub.1-4 -alkyl, C.sub.1-3 -alkoxy or C.sub.1-3 -halogenoalkyl,
A represents optionally halogen-substituted straight-chain or branched C.sub.1-10 -alkyl, C.sub.3-6 -alkenyl, C.sub.3-8 -alkinyl, C.sub.1-8 -alkoxy-C.sub.2-6 -alkyl, C.sub.1-6 -polyalkoxy-C.sub.2-6 -alkyl, C.sub.1-8 -alkylthio-C.sub.2-6 -alkyl, cycloalkyl which has 3-7 ring atoms and which can be interrupted by 1-2 oxygen and/or sulphur atoms, or represents aryl-C.sub.1-4 -alkyl which is optionally substituted by halogen, C.sub.1-4 -alkyl, C.sub.1-4 -halogenoalkyl, C.sub.1-4 -alkoxy or nitro,
B represents phenyl or benzyl which are optionally monosubstituted or disubstituted by identical or different substituents selected from the group consisting of nitro, fluorine, chlorine, bromine, optionally fluorine- or chlorine-substituted C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy,
and the pure enantiomeric forms of compounds of the formula (I).

### Claim 4 (depends on 1)

A composition for combating insects, acarids, and fungi, said composition comprising an effective amount therefor of a 3-aryl-4-hydroxy-pyrrolidin-2-one in the formula (I) according to claim 1 and a carrier.

### Claim 5 (depends on 1)

A method of combating insects, arachnids and fungi, comprising applying an effective amount therefor of a 3-aryl-4-hydroxy-pyrrolidin-2-one of the formula (I) according to claim 1 to said insects, arachnids or fungi or to the habitat of said insects, arachnids of fungi.

### Claim 6 (depends on 1)

An antimycotic composition comprising an antimycotically effective amount of a 3-aryl-4-hydroxy-pyrrolidin-2-one of the formula (I) according to claim 1 and a carrier.