# US 4,565,565 A · Dichloroacetamides, herbicides containing acetanilides as herbicidal active ingredients and the dichloroacetamides as antagonists, and the use of these herbicides in controlling undesired plant growth

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- Number: US 4,565,565 A
- Document ID: US4565565A
- Status: Granted
- Kind: A
- Application number: 06/519,821
- Filed: 1983-08-03
- Granted: 1986-01-21
- Earliest claimed: 1979-12-03
- Assignees: BASF SE
- Inventors: Wolfgang Rohr; Hanspeter Hansen; Peter Plath; Bruno Wuerzer
- Web page: https://patentgrep.com/patent/US4565565A

## CPC

- C12N 7/00: Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00)
- 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 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61K 35/12: Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells (vaccines or medicinal preparations containing antigens or antibodies A61K39/00)
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C12N 1/02: Separating microorganisms from their culture media
- G01N 33/5434: {using magnetic particle immunoreagent carriers which constitute new materials per se}
- G01N 33/544: the carrier being organic
- C12M 47/04: {Cell isolation or sorting (purging biological preparations of unwanted cells C12N5/0081, determining the presence or kind of microorganism C12Q1/04)}
- C12N 2710/16051: Methods of production or purification of viral material
- G01N 2333/31: from Staphylococcus (G)
- G01N 2333/76: Assays involving albumins other than in routine use for blocking surfaces or for anchoring haptens during immunisation
- G01N 2446/20: the magnetic material being present in the particle core
- G01N 2446/30: the magnetic material being dispersed in the polymer composition before their conversion into particulate form
- G01N 2446/84: Polymer coating, e.g. gelatin
- Y10S 436/828: Protein A
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- 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
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C12M: APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; {APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS}
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Novel dichloroacetamides of the formula (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, m, n, p and q have the meanings given in the description. The compounds are antagonists which increase the toleration, by crops, of herbicidal acetanilides. Herbicides containing the dichloroacetamides of the formula I in combination with acetanilides may be used for controlling undesired plant growth in Indian corn and cereals.

## Claims

### Claim 1

A herbicidal agent containing, as herbicidal active ingredient, an effective amount of at least one acetanilide of the formula ##STR43## where R.sup.7 is hydrogen or linear or branched alkyl or alkoxy of up to 5 carbon atoms,
R.sup.8 is hydrogen, halogen or linear or branched alkyl or alkoxy of up to 5 carbon atoms,
R.sup.9 is hydrogen, halogen or linear or branched alkyl or alkoxy of up to 5 carbon atoms,
R.sup.7 together with R.sup.8 may also be alkylene of up to 6 carbon atoms which is ortho-linked to the benzene ring and is unsubstituted or substituted by linear or branched alkyl of up to 4 carbon atoms,
X is chlorine or bromine and
A is alkoxy or alkoxyalkyl of up to 4 carbon atoms, or is an azole radical which is bonded via a ring nitrogen and which may be monosubstituted or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of up to 4 carbon atoms, cyano, carboxyl or alkoxycarbonyl, where alkoxy is of up to 4 carbon atoms, and may also be a salified azole radical if the azole ring contains 2 or 3 nitrogens,
and, as antagonist, an effective amount of at least one dichloroacetamide of the formula ##STR44## where R.sup.1 is hydrogen, methyl or ethyl,
R.sup.2 and R.sup.3 are identical or different and are hydrogen, methyl or methoxy,
R.sup.4 is hydrogen or methyl and
R.sup.5 and R.sup.6 are identical or different and are hydrogen or methyl, and
m is 0 or 1, n is 1 or 2, p is 0, 1 or 2 and q is 0, 1 or 2.

### Claim 2 (depends on 1)

A herbicidal agent as claimed in claim 1, wherein the ratio of acetanilide to dichloroacetamide, applied conjointly or separately, is from 1:2 to 1:0.01 parts by weight.

### Claim 3 (depends on 1)

A process for the selective control of unwanted plants, wherein the acetanilide of the formula II and the dichloroacetamide of the formula I as claimed in claim 1 are applied, simultaneously or one after the other in any sequence, before, during or after sowing of the crop plants, or before or during emergence of the crop plants.

### Claim 4 (depends on 1)

A process for the selective control of unwanted plants with acetanilides of the formula II, wherein the crop plant seed is treated with a dichloroacetamide of the formula I as claimed in claim 1.

### Claim 5 (depends on 3)

A process as set forth in claim 3 wherein the crop plant is a cereal.

### Claim 6 (depends on 4)

A process as set forth in claim 4 wherein the crop plant is a cereal.

### Claim 7 (depends on 1)

A herbicidal agent as set forth in claim 1, wherein the sum of p+q in the compound of formula I is 1 or 2.

### Claim 8 (depends on 1)

A herbicidal agent as defined in claim 1, wherein the acetanilide of the formula II is selected from the group consisting of 2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(pyrazol-1-yl-methyl)-acetanilide, 2-chloro-2',6'-dimethyl-N-(4-methyl-pyrazol-1-yl-methyl)-acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(4-methoxy-pyrazol-1-yl-methyl)-acetanilide, 2-chloro-2',6'-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(3-methylpyrazol-1-yl-methyl)-acetanilide, 2-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide and 2-chloro-2',3',6'-trimethyl-N-(pyrazol-1-yl-methyl)-acetanilide.

### Claim 9 (depends on 1)

A herbicidal agent as defined in claim 1, wherein A an is azole radical and the antagonist is selected from the group consisting of 5-dichloroacetyl-6-methyl-9-oxo-1,5-diazabicyclo[4.3.0]-nonane and 5-dichloroacetyl-3,3,6-trimethyl-9-oxo-1,5-diazabicyclo[4.3.0]nonane.

### Claim 10 (depends on 1)

A herbicidal agent as defined in claim 1, wherein the acetanilide of the formula II is 2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide and wherein the antagonist of formula I is selected from the group consisting of 5-dichloroacetyl-6-methyl-9-oxo-1,5-diazabicyclo[4.3.0]-nonane and 5-dichloroacetyl-3,3,6-trimethyl-9-oxo-1,5-diazabicyclo[4,3.0]nonane.

### Claim 11 (depends on 3)

A process as set forth in claim 3, wherein the crop plant is Indian corn.

### Claim 12 (depends on 4)

A process as set forth in claim 4, wherein the crop plant is Indian corn.