# US 5,707,935 A · Herbicidal compounds

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- Number: US 5,707,935 A
- Document ID: US5707935A
- Status: Granted
- Kind: A
- Application number: 08/699,720
- Filed: 1996-08-06
- Granted: 1998-01-13
- Earliest claimed: 1993-10-08
- Assignees: American Cyanamid Company
- Inventors: Wolfgang Buck
- Web page: https://patentgrep.com/patent/US5707935A

## CPC

- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero 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

A compound of the general formula ##STR1## wherein A represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl or aralkyl group, or a group of general formula X--Y--(CH.sub.2)n-- where X represents an optionally substituted alkyl or aryl group, n represents 1 or 2, and Y represents an oxygen atom or a group of general formula --S(O).sub.m - where m represents 0, 1 or 2; R.sup.1 represents a hydrogen atom or an alkyl group; and R.sup.2 represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl group. Also disclosed are preparative processes, and novel intermediates.

## Claims

### Claim 1

A method of combating undesired plant growth at a locus comprising application to the locus of a herbicidal composition which composition comprises an agronomically acceptable carrier, and at least one compound of formula I ##STR4## wherein A represents an optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl group;
R.sup.1 represents a hydrogen atom or an alkyl group;
R.sup.2 represents an optionally substituted aralkyl or heteroaralkyl group; wherein the optional substituents for alkyl, alkenyl, alkynyl, and cycloalkyl, and alkyl portions of aralkyl or heteroaralkyl groups are independently selected from the group consisting of halogen, nitro, cyano, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C.sub.1-4 alkoxycarbonyl, amino, alkyl- and phenyl-sulphinyl, -sulphenyl and -sulphonyl, and C.sub.1-4 alkylamino groups, and optional substituents for aryl portions of aralkyl and heteroaralkyl groups are independently selected from the group consisting of halogen, amino, nitro, cyano, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, and C.sub.1-4 alkoxy groups.

### Claim 2 (depends on 1)

A method according to claim 1, wherein in said at least one compound of formula I A represents a branched alkyl, alkenyl, or alkynyl group containing up to 6 carbon atoms.

### Claim 3 (depends on 1)

A method according to claim 1, wherein in said at least one compound of formula I A represents a branched alkyl group having 3 to 6 carbon atoms.

### Claim 4 (depends on 1)

A method according to claim 1, wherein in said at least one compound of formula I
R.sup.1 represents a hydrogen atom; and
R.sup.2 represents optionally substituted heteroaralkyl.

### Claim 5 (depends on 4)

A method according to claim 4 wherein in said at least one compound of formula I
R.sup.1 represents a hydrogen atom; and
R.sup.2 represents a group of formula
--CH(R.sup.3)--R.sup.4,
in which
R.sup.3 represents hydrogen or a C.sub.1-4 alkyl group; and
R.sup.4 represents a pyridyl, furyl or thienyl group.

### Claim 6 (depends on 5)

A method according to claim 5, wherein in said at least one compound of formula I
A represents a branched alkyl group having 3 to 6 carbon atoms;
R.sup.1 represents a hydrogen atom; and
R.sup.2 represents a group of formula
--CH(R.sup.3)--R.sup.4,
in which
R.sup.3 represents hydrogen or a C.sub.1-4 alkyl group; and
R.sup.4 represents a pyridyl, furyl or thienyl group.

### Claim 7 (depends on 5)

A method according to claim 5 wherein said at least one compound of formula I is optically active and R.sup.1 represents a hydrogen atom; and
R.sup.2 represents a chiral group having (S)-configuration of formula
--CH(R.sup.3)--R.sup.4,
in which
R.sup.3 represents a C.sub.1-4 alkyl group; and
R.sup.4 represents a pyridyl, furyl or thienyl group.