# US 5,707,932 A · Herbicidal picolinamide derivatives

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- Number: US 5,707,932 A
- Document ID: US5707932A
- Status: Granted
- Kind: A
- Application number: 08/325,173
- Filed: 1995-08-04
- Granted: 1998-01-13
- Earliest claimed: 1992-10-22
- Assignees: American Cyanamid Company
- Inventors: Axel Kleemann; Robert John Griffith Searle
- Web page: https://patentgrep.com/patent/US5707932A

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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

Herbicidal picolinamide derivatives are provided having the formula I ##STR1## which Z represents an oxygen or sulphur atom, R.sup.1 and R.sup.2 each independently represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, alkylcarbonyl, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, arylalkylamino or dialkylcarbamoyl group, or together represent an alkylene chain which is optionally interrupted by an oxygen or sulphur atom or by a group --NR-- in which R represents a hydrogen atom or an alkyl group, R.sup.3 independently represents a halogen atom or an alkyl or haloalkyl group, R.sup.4, R.sup.5 and R.sup.6 each independently represents a hydrogen or halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, alkoxy, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, dialkylcarbamoyl, acyl or acylamido group or a cyano group, with the proviso that R.sup.5 and R.sup.6 do not represent an acyl, acylamido or cyano group, and n represents 0, 1, 2 or 3.

## Claims

### Claim 1

A compound of the formula I ##STR22## in which Z represents an oxygen or sulphur atom,
R.sup.1 and R.sup.2 each independently represents a hydrogen atom or an optionally substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-8 cycloalkyl, (C.sub.3-8 cycloalkyl) C.sub.1-10 alkyl, C.sub.6-10 aryl, C.sub.6-10 arylC.sub.1-10 alkyl or C.sub.1-10 alkylC.sub.6-10 aryl group or one but not both of R.sup.1 and R.sup.2 may additionally represent a hydroxy group or an optionally substituted C.sub.1-10 alkoxy, C.sub.2-10 alkenyloxy, C.sub.2-10 alkynyloxy, C.sub.1-10 alkylcarbonyl, amino, mono- or di-C.sub.1-10 alkylamino, C.sub.1-10 alkoxycarbonylamino, C.sub.6-10 arylamino, C.sub.6-10 arylC.sub.1-10 alkylamino or diC.sub.1-10 alkylcarbamoyl group,
R.sup.3 independently represents a halogen atom, a C.sub.1-10 alkyl, C.sub.1-10 alkoxy, C.sub.1-10 alkylthio, diC.sub.1-10 alkylamino or C.sub.1-10 haloalkyl group,
R.sup.4 represents a hydrogen or halogen atom, an optionally substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-8 cycloalkyl, (C.sub.3-8 cycloalkyl) C.sub.1-10 alkyl, C.sub.6-10 aryl, C.sub.6-10 arylC.sub.1-10 alkyl, C.sub.1-10 alkylC.sub.6-10 aryl, C.sub.1-10 alkoxy, diC.sub.1-10 alkylcarbamoyl, acyl or a cyano group,
R.sup.5 and R.sup.6 each independently represents a hydrogen or halogen atom, an optionally substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-8 cycloalkyl, (C.sub.3-8 cycloalkyl)C.sub.1-10 alkyl, C.sub.6-10 aryl, C.sub.6-10 arylC.sub.1-10 alkyl, C.sub.1-10 alkylC.sub.6-10 aryl, C.sub.1-10 alkoxy, amino, mono-or di-C.sub.1-10 alkylamino, C.sub.1-10 alkoxycarbonylamino, C.sub.6-10 arylamino, diC.sub.1-10 alkylcarbamoyl group, and
n represents 0, 1, 2 or 3, and in which said optional substituents are selected from the group consisting of halogen atoms or nitro, cyano, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, formyl, C.sub.1-6 alkoxycarbonyl, carboxyl, phenyl or amino groups, said amino optionally substituted by one or two groups selected from C.sub.1-10 alkyl, C.sub.6-10 aryl, C.sub.3-8 cycloalkyl, (C.sub.3-8 cycloalkyl)C.sub.1-10 alkyl, C.sub.6-10 arylC.sub.1-10 alkyl, and C.sub.1-10 alkylC.sub.6-10 aryl.

### Claim 2 (depends on 1)

A compound according to claim 1, in which Z represents an oxygen atom.

### Claim 3 (depends on 1)

A compound according to claim 1 in which R.sup.1 and R.sup.2 each independently represents a hydrogen atom or a C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.3-6 cycloalkyl, (C.sub.3-6 cycloalkyl) C.sub.1-8 alkyl, C.sub.1-6 alkoxy, phenyl, naphthyl, phen-C.sub.1-6 alkyl, C.sub.1-8 alkylamino, C.sub.1-6 dialkylamino or phenylamino group, each group optionally substituted by one or more halogen atoms, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylamino, C.sub.1-4 dialkylamino, cyano or phenyl amino groups.

### Claim 4 (depends on 1)

A compound according to claim 1 in which R.sup.3 represents a methyl, methoxy, methylthio or dimethylamino group.

### Claim 5 (depends on 1)

A compound according to claim 1 in which R.sup.4, R.sup.5 and R.sup.6 each independently represents a hydrogen atom, a cyano group, a C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 acyl, C.sub.2-4 alkenyl, phenyl or naphthyl group, each group optionally substituted by one, more halogen atoms or C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylamino, C.sub.1-4 dialkylamino or C.sub.6-10 aryl amino groups.

### Claim 6 (depends on 1)

A herbicidal composition which comprises, as active ingredient, a compound as claimed in claim 1, together with at least one carrier.

### Claim 7 (depends on 6)

The composition of claim 6 which comprises at least two carriers, at least one of which is a surface active agent.

### Claim 8 (depends on 1)

A method of combating undesired plant growth at a locus, which comprises treating the locus with a compound as claimed in claim 1.

### Claim 9 (depends on 8)

A method of combating undesired plant growth at a locus, which comprises treating the locus with a composition as claimed in claim 8.

### Claim 10 (depends on 1)

A process for the preparation of a compound of the formula I as defined in claim 1, which comprises reacting a compound of the formula II, ##STR23## or an activated derivative thereof wherein the hydroxy group of the acid function is replaced by a leaving group selected from the group consisting of halogen, C.sub.1-4 alkoxy and imidazole group, and in which R.sup.3 and n are as defined in claim 1, and Q represents a leaving group selected from the group consisting of halogen, C.sub.1-4 alkoxy, C.sub.1-6 alkyl or aryl-sulphonium group, and C.sub.1-6 alkyl or aryl-sulphonic acid group, with a compound of the formula III
HNR.sup.1 R.sup.2 III
in which the substituents are as defined in claim 1 and, followed by reaction of the product thus obtained with a compound of the formula ##STR24## in which the substituents are defined in claim 1, while in the case that R.sup.1 and/or R.sup.2 represents a hydrogen atom, the hydrogen atom may be exchanged by another substituent within the definition of R.sup.1 and/or R.sup.2 by reaction with an alkylating agent.