# US 4,394,156 A · Novel N-phenyl-substituted N-heterocyclic compounds, their preparation and use in agents for regulating plant growth

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,394,156 A
- Document ID: US4394156A
- Status: Granted
- Kind: A
- Application number: 06/314,620
- Filed: 1981-10-26
- Granted: 1983-07-19
- Earliest claimed: 1977-04-15
- Assignees: Ciba-Geigy Corporation
- Inventors: Hans Tobler; Werner Fory; Rolf Schurter
- Web page: https://patentgrep.com/patent/US4394156A

## CPC

- C07D 213/64: attached in position 2 or 6
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- 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 present invention relates to novel active compounds having a plant growth-inhibiting and herbicidal action and their preparation and to agents containing these active ingredients, and their use. The novel active compounds are saturated and unsaturated 4-membered to 7-membered ring nitrogen heterocyclic compounds which are substituted on the nitrogen atom by a phenyl radical which itself carries a trifluoromethanesulphonamido group -NH-SO.sub.2 -CF.sub.3 as a substituent. The phenyl radical can also carry other substituents and the heterocyclic structure can also be substituted. Oxo derivatives of the heterocyclic compound, in which the oxo group is preferably adjacent to the nitrogen atom, form a preferred sub-group of compounds.

## Claims

### Claim 1

A compound of the formulae Ia or Ib. ##STR47## or a salt thereof formed with a cation selected from the group consisting of alkali metals, alkaline earth metals, zinc, copper, iron and organic amines, in which formulae
R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl portion, carboxyl, halogen or cyano, and
X and Z independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.5 alkoxy or halogen.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein the heterocyclic ring can be substituted by carboxyl, alkoxycarbonyl and one or more radicals selected from the group halogen, cyano or alkyl.

### Claim 3

The compound 1-(3'-trifluoromethanesulfonamido-4',6'-dimethylphenyl)-3-cyano-4,6-dimeth yl-2-pyridone.

### Claim 4

The compound 1-(3'-trifluoromethanesulfonamido-4',6'-dimethylphenyl)-3-carboxyl-4,6-dim ethyl-2-pyridone.

### Claim 5

The compound 1-(3'-trifluoromethanesulfonamido-4',6'-dimethylphenyl)-3-methoxycarbonyl- 4,6-dimethyl-2-pyridone.

### Claim 6 (depends on 1)

A composition for regulating plant growth which contains, in addition to carrier materials, an effective plant growth regulating amount of at least one trifluoromethanesulphonamido-phenyl-substituted heterocyclic compound according to claim 1 as the active component.

### Claim 7 (depends on 1)

A process for inhibiting and suppressing the plant growth of monocotyledonous and dicotyledonous plants, which comprises the pre-emergence or post-emergence treatment of the sown areas or of the plants with an effective growth inhibiting amount of an active compound according to claim 1.

### Claim 8 (depends on 1)

A process for inhibiting the growth of grasses, cereal crops, tobacco, soya and ornamental plants, which comprises the post-emergence treatment of these plants with an effective growth inhibiting amount of an active compound according to claims 1.