# US 5,705,456 A · Herbicides

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

- Number: US 5,705,456 A
- Document ID: US5705456A
- Status: Granted
- Kind: A
- Application number: 08/758,537
- Filed: 1996-11-29
- Granted: 1998-01-06
- Earliest claimed: 1995-12-01
- Assignees: Zeneca Limited
- Inventors: Glynn Mitchell; Stephen Christopher Smith
- Web page: https://patentgrep.com/patent/US5705456A

## CPC

- C07D 207/273: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- A01N 43/44: three- or four-membered rings
- A01N 43/74: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- C07D 263/28: Nitrogen atoms not forming part of a nitro radical
- C07D 277/18: Nitrogen atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- 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

Compounds of formula I: ##STR1## where n is 0 or an integer from 1 to 5; X is halogen, nitro or cyano, or C.sub.1-10 hydrocarbyl or C.sub.1-10 hydrocarbyloxy, either of which may be substituted with one or more halogen atoms; Y is CH.sub.2, O or S; and R.sup.1 and R.sup.2 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl or halogen; Processes for the preparation of compounds of formula I, herbicidal compositions and methods utilising them are also disclosed.

## Claims

### Claim 1

A compound of formula I: ##STR8## wherein n is 0 or an integer from 1 to 5; X is halogen, nitro or cyano, or C.sub.1-10 hydrocarbyl or C.sub.1-10 hydrocarbyloxy, either of which may be substituted with one or more halogen atoms;
Y is CH.sub.2, O or S; and
R.sup.1 and R.sup.2 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl C.sub.2-6 alkenyl, C.sub.2-6 alkynyl or halogen.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1, wherein n is an integer from 1 to 5.

### Claim 3 (depends on 1)

A compound of formula I according to claim 1, wherein X is halogen, or C.sub.1-10 hydrocarbyl or C.sub.1-10 hydrocarbyloxy, either of which may be substituted with one or more halogen atoms.

### Claim 4 (depends on 1)

A compound of formula I according to claim 1, wherein R.sup.1 and R.sup.2 independently represent C.sub.1-6 alkyl, C.sub.1-6 haloalkyl or halogen.

### Claim 5 (depends on 1)

A compound of formula I according to claim 1 which is:
1-›1-(3-Trifluoromethoxyphenyl)pyrrolidin-2-one-3-yl!-3,3-dimethylazetidin- 2-one;
1-›1-(3-Trifluoromethoxyphenyl)pyrrolidin-2-one-3-yl!-3-chloro-3-methylazet idin-2-one;
1-›1-(3-Trifluoromethoxyphenyl)pyrrolidin-2-one-3-yl!-3-chloromethyl-3-meth ylazetidin-2-one;
1-›1-(3-Trifluoromethoxyphenyl)pyrrolidin-2-one-3-yl!-3-bromo-3-methylazeti din-2-one;
1-›3-(3-Trifluoromethoxyphenyl)thiazolidin-4-one-5-yl!-3,3-dimethylazetidin -2-one;
1-›3-(3-Trifluoromethoxyphenyl)thiazolidin-4-one-5-yl!-3-bromo-3-methylazet idin-2-one;
1-›3-(3-Trifluoromethoxyphenyl)thiazolidin-4-one-5-yl!-3-chloromethyl-3-met hylazetidin-2-one;
1-›3-(3-Trifluoromethoxyphenyl)thiazolidin-4-one-5-yl!-3-chloro-3-methylaze tidin-2-one;
1-›3-(3-Trifluoromethoxyphenyl)oxazolidin-4-one-5-yl!-3,3-dimethylazetidin- 2-one;
1-›1-(3-Trifluoromethoxyphenyl)oxazolidin-4-one-5-yl!-3-chloromethyl-3-meth ylazetidin-2-one;
1-›3-(3-Trifluoromethoxyphenyl)oxazolidin-4-one-5-yl!-3-bromo-3-methylazeti din-2-one;
1-›3-(3-Trifluoromethoxyphenyl)oxazolidin-4-one-4-yl!-3-chloro-3-methylazet idin-2-one;
1-›1-(3-Chloro-4-fluorophenyl)pyrrolidin-2-one-3-yl!-3,3-dimethylazetidin-2 -one; or
1-›1-(3,5-Dichlorophenyl)pyrrolidin-2-one-3-yl!-3,3-dimethylazetidin-2-one.

### Claim 6 (depends on 1)

A process of severely damaging or killing unwanted plants, which process comprises applying to the plants, or to the growth medium of the plants, a herbicidally effective amount of a compound of formula I according to claim 1.

### Claim 7 (depends on 1)

A herbicidal composition, comprising as an active ingredient a compound of formula I according to claim 1, in admixture with a carrier comprising a solid or liquid diluent, and optionally a surface-active agent.