# US 4,392,882 A · N-N-Bis(haloacyl)-diaza-cycloalkanes for protecting plants from herbicide damage

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- Number: US 4,392,882 A
- Document ID: US4392882A
- Status: Granted
- Kind: A
- Application number: 06/166,412
- Filed: 1980-07-07
- Granted: 1983-07-12
- Earliest claimed: 1979-07-26
- Assignees: Bayer Aktiengesellschaft
- Inventors: Hans-Jochem Riebel; Ludwig Eue; Wilfried Faust
- Web page: https://patentgrep.com/patent/US4392882A

## CPC

- C07D 295/185: from aliphatic carboxylic acids
- 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
- C07D 243/08: not condensed with other 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

The use of N,N'-bis-(haloacyl)-diaza-cycloalkanes of the general formula ##STR1## in which R.sup.1 represents alkyl or halogen, R.sup.2 represents halogen, R.sup.3 represents alkyl or halogen, R.sup.4 represents halogen, R.sup.5 represents hydrogen or alkyl with 1 to 4 carbon atoms, R.sup.6 represents hydrogen or alkyl with 1 to 4 carbon atoms and Q represents an alkylene chain which has 2 or 3 carbon atoms in the alkylene chain and is optionally monosubstituted or polysubstituted by alkyl with 1 to 4 carbon atoms, as antidotes for protecting crop plants from damage by herbicides.

## Claims

### Claim 1

Method for protecting maize from damage by herbicidally active acetanilides of the formula ##STR101## wherein R represents pyrazol-1-yl -or pyrazol-1-yl substituted by halogen or alkyl with 1 to 4 carbon atoms,
X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms,
Z represents chlorine and
n represents 0,1 or 2, and herbicidally active acid addition salts and metal salt complexes thereof, which comprises applying to the plants or their habitat an antidotally effective amount of N,N'-bis-(haloacyl)-diazacycloalkane compound of the formula ##STR102## wherein R.sup.1 is methyl or chlorine;
R.sup.2 is chlorine;
R.sup.3 is methyl or chlorine;
R.sup.4 is chlorine;
R.sup.5 is hydrogen or alkyl with 1 or 2 carbon atoms;
R.sup.6 is hydrogen or alkyl with 1 or 2 carbon atoms; and
Q is an alkylene chain which has 2 or 3 carbon atoms and can be mono-substituted by methyl.

### Claim 2 (depends on 1)

Method as claimed in claim 1 wherein the active 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 the active compound is applied to seed in an amount of 10 to 200 per gram kg of seed.

### Claim 4

Herbicidal composition for use in maize comprising a herbicidally active compound selected from acetanilide herbicides of the formula ##STR103## in which R represents pyrazol-1-yl or pyrazol-1-yl substituted by halogen or alkyl with 1 to 4 carbon atoms,
X and Y are identical or different and represent alkyl with 1 to 4 carbon atoms,
Z represents halogen and
n represents 0,1 or 2, and herbicidally active acid addition salts and metal salt complexes thereof, and as an antidote, an N,N'-bis-(haloacyl)-diaza-cycloalkane compound of the formula ##STR104## wherein R.sup.1 is methyl or chlorine;
R.sup.2 is chlorine;
R.sup.3 is methyl or chlorine;
R.sup.4 is chlorine;
R.sup.5 is hydrogen or alkyl with 1 or 2 carbon atoms;
R.sup.6 is hydrogen or alkyl with 1 or 2 carbon atoms; and
Q is an alkylene chain which has 2 or 3 carbon atoms and can be mono-substituted by methyl.

### Claim 5 (depends on 4)

Herbicidal composition as claimed in claim 4 containing from 0.05 to 1 part by weight of the compound of formula (I) per part by weight of said herbicidally active compound.

### Claim 6 (depends on 4)

Herbicidal composition as claimed in claim 4 containing from 0.1 to 0.5 part by weight of the compound of formula (I) per part by weight of said herbicidally active compound.

### Claim 7 (depends on 4)

Method of combating weeds in maize comprising applying to the weeds or their habitat a composition as claimed in claim 4.

### Claim 8 (depends on 7)

Method as claimed in claim 7 wherein the composition is applied at a rate corresponding to 0.5 to 5 kg of acetanilides per hectare.

### Claim 9 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote is N,N'-bis-(dichloroacetyl)-2,5-dimethyl-piperazine.

### Claim 10 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote is N,N'-bis-(alpha-chloropropionyl)-2,5-dimethyl-piperazine.

### Claim 11 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote is N,N'-bis-(dichloroacetyl)-hexahydro-1,4-diazepine.

### Claim 12 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote is N,N'-bis-(alpha-chloropropionyl)-hexahydro-1,4-diazepine.

### Claim 13 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote is N,N'-bis-(alpha-chloropropionyl)-piperazine.

### Claim 14 (depends on 4)

Herbicidal composition as claimed in claim 4 wherein said antidote compound is selected from
N,N'-bis(dichloroacetyl)-2,5-dimethylpiperazine;
N,N'-bis-(alpha-chloropropionyl)-2,5-dimethylpiperazine;
N,N'-bis-(dichloroacetyl)-hexahydro-1,4-diazepine;
N,N'-bis-(alpha-chloropropionyl)-hexahydro-1,4-diazepine; and
N,N'-bis-(alpha-chloropropionyl)-piperazine.

### Claim 15 (depends on 7)

Method as claimed in claim 7 wherein said antidote compound is selected from
N,N'-bis(dichloroacetyl)-2,5-dimethylpiperazine;
N,N'-bis-(alpha-chloropropionyl)-2,5-dimethylpiperazine;
N,N'-bis-(dichloroacetyl)-hexahydro-1,4-diazepine;
N,N'-bis-(alpha-chloropropionyl)-hexahydro-1,4-diazepine; and
N,N'-bis-(alpha-chloropropionyl)-piperazine.