# US 5,344,813 A · Hydroxypyridonecarboxamides, their manufacture and use as herbicides

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- Number: US 5,344,813 A
- Document ID: US5344813A
- Status: Granted
- Kind: A
- Application number: 07/981,361
- Filed: 1992-11-25
- Granted: 1994-09-06
- Earliest claimed: 1991-11-26
- Assignees: BASF SE
- Inventors: Hans Theobald; Wolfgang von Deyn; Christoph Nuebling; Helmut Walter; Uwe Kardorff; Karl-Otto Westphalen; Thomas Kappe; Matthias Gerber
- Web page: https://patentgrep.com/patent/US5344813A

## CPC

- C07D 213/82: in position 3
- A01N 43/40: six-membered rings
- C07D 213/83: Thioacids; Thioesters; Thioamides; Thioimides
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Hydroxypyridonecarboxamides of the formula I ##STR1## where: X is oxygen or sulfur; R.sup.1, R.sup.2 independently of each other are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or alkoxy, and these organic radicals are substituted or unsubstituted; R.sup.3 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, halogen or nitro; R.sup.4 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, phenyl or a 5- or 6-membered heterocyclic, aliphatic or aromatic radical containing from one to three heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and these radicals are substituted or unsubstituted; with the exception of 6-methyl-4-hydroxypyrid-2-one-3-carboxamide and 6-methyl-4-hydroxypyrid-2-one-3-carboxylic acid-tert-butylamide.

## Claims

### Claim 1

A hydroxypyridonecarboxamide of the formula I, ##STR55## where: X is oxygen or sulfur;
R.sup.1, R.sup.2 independently of each other are hydrogen, straight-chain or branched C.sub.1 -C.sub.25 -alkyl, C.sub.3 -C.sub.25 -alkenyl, C.sub.3 -C.sub.25 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.17 -alkyl or C.sub.1 -C.sub.25 -alkoxy, the organic radicals being optionally substituted by halogen, cyano, C.sub.1 -C.sub.5 -alkylcarbonyl, C.sub.1 -C.sub.5 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, or C.sub.1 -C.sub.6 -haloalkylthio;
R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, halogen or nitro;
R.sup.4 is C.sub.1 -C.sub.10 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 -alkylthio, phenyl, the said radicals being optionally substituted by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -haloalkylthio or phenyl optionally substituted by a member selected from the group consisting of halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -haloalkoxy and C.sub.1 -C.sub.3 -alkoxyl;
and environmentally acceptable salts thereof, with the exception of 6-methyl-4-hydroxypyrid-2-one-3-carboxamide and 6-methyl-4-hydroxypyrid-2-one-3-carboxylic acid-tert-butylamide.

### Claim 2 (depends on 1)

A hydroxypyridonecarboxamide of the formula I as set forth in claim 1, where X and the radicals R.sup.1 to R.sup.4 have the following meanings:
X is oxygen or sulfur;
R.sup.1 is hydrogen;
R.sup.2 is branched or straight-chain C.sub.1 -C.sub.15 -alkyl, C.sub.3 -C.sub.15 -alkenyl, C.sub.3 -C.sub.15 -alkynyl, C.sub.1 -C.sub.15 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl, and these radicals are optionally substituted by halogen, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy or phenyl which is optionally substituted by from one to five halogen atoms and/or from one to three members selected from the group consisting of cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;
R.sup.3 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -haloalkylthio, halogen or nitro;
R.sup.4 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio or phenyl and the said radicals substituted by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -haloalkylthio, or phenyl optionally substituted by a member selected from the group consisting of halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl or C.sub.1 -C.sub.3 -haloalkoxy.

### Claim 3 (depends on 1)

A hydroxypyridonecarboxamide of the formula I as set forth in claim 1, where X and the radicals R.sup.1 to R.sup.4 have the following meanings:
X is oxygen or sulfur;
R.sup.1 is hydrogen;
R.sup.2 is branched or straight-chain C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.1 -C.sub.4 -alkoxy;
R.sup.3 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, halogen or nitro;
R.sup.4 is C.sub.1 -C.sub.6 -alkyl or phenyl, each of which is optionally substituted by from one to three radicals selected from the group consisting of halogen, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -haloalkylthio or substituted or unsubstituted phenyl optionally substituted by a member selected from the group consisting of halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl or C.sub.1 -C.sub.3 -haloalkoxy.

### Claim 4 (depends on 1)

A herbicidal composition comprising an effective amount of a hydroxypyridonecarboxamide of the formula I as set forth in claim 1 and conventional inert additives.

### Claim 5

A method of combating the growth of unwanted plants, wherein the unwanted plants and/or their habitat are treated with a herbicidally effective amount of a hydroxypyridonecarboxamide of the formula I ##STR56## where: X is oxygen or sulfur;
R.sup.1, R.sup.2 independently of each other are hydrogen, straight-chain or branched C.sub.1 -C.sub.25 -alkyl, C.sub.3 -C.sub.25 -alkenyl, C.sub.3 -C.sub.25 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.17 -alkyl or C.sub.1 -C.sub.25 -alkoxy, the organic radicals being optionally substituted by halogen, cyano, C.sub.1 -C.sub.5 -alkylcarbonyl, C.sub.1 -C.sub.5 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, or phenyl which in turn is optionally substituted by from one to five halogen atoms and/or from one to three members selected from the group consisting of cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;
R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, halogen or nitro; R.sup.4 is C.sub.1 -C.sub.10 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkynyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 -alkylthio, phenyl, the said radicals being optionally substituted by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -haloalkylthio, or phenyl optionally substituted by a member selected from the group consisting of halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkyl and C.sub.1 -C.sub.3 -haloalkoxy.

### Claim 6 (depends on 1)

A hydroxypyridonecarboxamide of the formula I as set forth in claim 1, wherein X is oxygen, R.sup.1 is hydrogen, R.sup.2 is isopropyl, R.sup.3 is hydrogen, and R.sup.4 is methyl.

### Claim 7 (depends on 2)

A method of combating the growth of unwanted plants, wherein the unwanted plants and/or their habitat are treated with a herbicidally effective amount of a hydroxypyridonecarboxamide of the formula I as defined in claim 2.

### Claim 8 (depends on 3)

A method of combating the growth of unwanted plants, wherein the unwanted plants and/or their habitat are treated with a herbicidally effective amount of a hydroxypyridonecarboxamide of the formula I as defined in claim 3.