# US 4,396,416 A · N-Acyl-piperidon compounds and their use as antidotes for protecting crop plants from herbicidal damage

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- Number: US 4,396,416 A
- Document ID: US4396416A
- Status: Granted
- Kind: A
- Application number: 06/252,982
- Filed: 1981-04-10
- Granted: 1983-08-02
- Earliest claimed: 1979-09-21
- Assignees: Bayer Aktiengesellschaft
- Inventors: Hans-Jochem Riebel; Ludwig Eue; Wilfried Faust
- Web page: https://patentgrep.com/patent/US4396416A

## CPC

- C07D 211/74: Oxygen atoms
- A01N 25/32: Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- A01N 43/40: six-membered rings
- 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

N-Acyl-piperidones of the formula ##STR1## wherein R represents methyl or chloro, and their use as antidotes for protecting crop plants from herbicidal damage.

## Claims

### Claim 1

Method for the protection of maize from damage by herbicidally active acetanilides of the formula ##STR21## in which R.sup.4 is pyrazol-1-yl or pyrazol-1-yl substituted by one or more radicals selected from fluorine, chlorine, bromine and alkyl with one to four carbon atoms,
X and Y are identical or different and represent alkyl with one to four carbon atoms,
Z represents halogen and
n represents 0, 1 or 2,
which method comprises applying to the maize plants or to their habitat, an antidotally effective amount of an N-acyl-piperidone compound of the formula ##STR22## wherein R is methyl or chloro.

### Claim 2 (depends on 1)

Method as claimed in claim 1 wherein said compound is applied to an area of agriculture in an amount of from 0.1 to 5 kg per hectare.

### Claim 3 (depends on 1)

Method as claimed in claim 1 wherein said compound is applied to seed in an amount of 10 to 300 grams per kg of seed.

### Claim 4 (depends on 1)

Method as claimed in claim 1 wherein said antidotal compound is selected from
N-dichloroacetyl-piperid-4-one and
N-(.alpha.-chloropropionyl)-piperid-4-one.

### Claim 5

Herbicidal composition comprising an herbicidally active compound selected from acetanilide herbicides of the formula ##STR23## in which R.sup.4 is pyrazol-1-yl or pyrazol-1-yl substituted by one or more radicals selected from fluorine, chlorine, bromine and alkyl with one to four carbon atoms,
X and Y are identical or different and represent alkyl, with one to four carbon atoms,
Z represents halogen and
n represents 0, 1 or 2, and, as an antidote, an effective amount of an N-acyl-piperidone compound of the formula ##STR24## wherein R is methyl or chloro.

### Claim 6 (depends on 5)

Herbicidal composition as claimed in claim 5 containing from 0.1 to 95% of a mixture consisting of an N-acyl-piperidone compound and a herbicidally active compound selected from thiolcarbamates and acetanilide herbicides.

### Claim 7 (depends on 5)

Herbicidal composition as claimed in claim 5 containing from 0.04 to 1 part by weight of said antidote compound per part by weight of said herbicidally active compound.

### Claim 8 (depends on 5)

Herbicidal composition as claimed in claim 5 containing from 0.1 to 0.5 part by weight of said antidote compound per part by weight of said herbicidally active compound.

### Claim 9 (depends on 5)

Herbicidal composition as claimed in claim 5 wherein said antidotal compound is selected from
N-dichloroacetyl-piperid-4-one and
N-(.alpha.-chloropropionyl)-piperid-4-one.