# US 7,608,564 B2 · 3-heterocyclyl-substituted benzoyl derivatives

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- Number: US 7,608,564 B2
- Document ID: US7608564B2
- Status: Granted
- Kind: B2
- Application number: 11/739,928
- Filed: 2007-04-25
- Published: 2008-02-14
- Granted: 2009-10-27
- Earliest claimed: 1997-01-17
- Assignees: BASF SE
- Inventors: Wolfgang von Deyn; Regina Luise Hill; Uwe Kardorff; Ernst Baumann; Stefan Engel; Guido Mayer; Matthias Witschel; Michael Rack; Norbert Götz; Joachim Gebhardt; Ulf Miβlitz; Helmut Walter; Karl-Otto Westphalen; Martina Otten; Joachim Rheinheimer
- Web page: https://patentgrep.com/patent/US7608564B2

## CPC

- C07D 413/10: linked by a carbon chain containing aromatic rings
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C07D 231/20: One oxygen atom attached in position 3 or 5
- C07D 261/04: having one double bond between ring members or between a ring member and a non-ring member
- C07D 261/20: condensed with carbocyclic rings or ring systems
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 417/10: linked by a carbon chain containing aromatic 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

Benzoyl derivatives of the formula I where the variables have the following meanings: R1, R2 are hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or C1-C6-haloalkylsulfonyl; R3 is hydrogen, halogen or alkyl; R4, R5 are hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, dialkylamino, phenyl or carbonyl, it being possible for the 6 last-mentioned radicals to be substituted; X is O, S, NR9, CO or CR10R11; Y is O, S, NR12, CO or CR13R14; R15 is pyrazole which is unsubstituted or substituted, linked in the 4-position and has attached to it in the 5-position a hydroxyl or sulfonyloxy radical; and the agriculturally useful salts thereof; processes and intermediates for the preparation of the 3-heterocyclyl-substituted benzoyl derivatives; compositions comprising them; and the use of these derivatives or compositions comprising them for controlling undesirable plants.

## Claims

### Claim 1

A 3-heterocyclyl-substituted benzoic acid compound of formula III,
wherein:
R19 is hydroxyl or a member selected from the group consisting of alkoxy, phenoxy, alkylthio and phenylthio radicals which are unsubstituted or substituted, halides, hetaryl radicals which are bonded via nitrogen; and amino, imino radicals which are unsubstituted or substituted,
R1, R2 is nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
R3 is hydrogen;
R4 is halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, C3-C8-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, COR6, phenyl or benzyl, it being possible for the two last-mentioned substituents to be partially or fully halogenated and/or to have attached to them one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C6-alkoxy or C1-C4-haloalkoxy;
R5 is C1-C4-alkyl;
R6 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy or NR7R8;
X is O;
Y is CR13R14;
R13, R14 are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl or CONR7R8;
R7 is hydrogen or C1-C4-alkyl; and
R8 is C1-C4-alkyl.

### Claim 2 (depends on 1)

The 3-heterocyclyl-substituted benzoic acid compound of formula III defined in claim 1, wherein R19 is halogen, hydroxyl or C1-C6-alkoxy.

### Claim 3

A 3-heterocyclyl-substituted benzoyl compound of formula I
wherein:
X is O;
R1, R2 is nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
R3 is hydrogen;
R4 is halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, C1-C8-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, COR6, phenyl or benzyl, it being possible for the two last-mentioned substituents to be partially or fully halogenated and/or to have attached to them one to three of the following groups: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R5 is C1-C4-alkyl;
R6 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-C4alkoxy, C1-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy or NR7R8;
Y is CR13R14;
R13, R14 are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl or CONR7R8;
R7 is hydrogen or C1-C4-alkyl;
R8 is C1-C4-alkyl;
R15 is a pyrazole of the formula II which is linked in the 4-position
wherein
R16 is methyl, ethyl, n-propyl or n-butyl;
Z is H or SO2R17;
R17 is C1-C4-, C1-C4-haloalkyl, phenyl or phenyl which is partially or fully halogenated and/or has attached to it one to three of the following groups:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; and
R18 is hydrogen or methyl.

### Claim 4 (depends on 3)

A composition comprising a herbicidally active amount of at least one 3-heterocyclyl-substituted benzoyl compound of formula I or of the agriculturally useful salt of formula I defined in claim 3, and auxiliaries conventionally used for the formulation of crop protection products.

### Claim 5 (depends on 4)

A process for the preparation of the composition defined in claim 4, which comprises mixing a herbicidally active amount of at least one 3-heterocyclyl-substituted benzoyl compound of the formula I or of the agriculturally useful salt of I and auxiliaries conventionally used for the formulation of crop protection products.

### Claim 6 (depends on 3)

A method of controlling undesirable vegetation, which comprises allowing a herbicidally active amount of at least one 3 -heterocyclyl-substituted benzoyl compound of the formula I or of the agriculturally useful salt of I defined in claim 3 to act on plants, their environment and/or on seeds.

### Claim 7 (depends on 3)

The 3-heterocyclyl-substituted benzoyl compound of the formula I defined in claim 3, wherein R1 is methyl, R2 is methylsulfonyl, R3 is hydrogen, R16 is methyl and R18 is hydrogen.

### Claim 8 (depends on 3)

The 3-heterocyclyl-substituted benzoyl compound of the formula I defined in claim 3, wherein R1 is methyl, R2 is methylsulfonyl, R3 is hydrogen, R16 is ethyl and R18 is hydrogen.

### Claim 9 (depends on 3)

The 3-heterocyclyl-substituted benzoyl compound of the formula I defined in claim 3, wherein R1 is methyl, R2 is methyl-sulfonyl, R3 is hydrogen, R16 is methyl and R18 is methyl.

### Claim 10 (depends on 3)

The 3-heterocyclyl-substituted benzoyl compound of the formula I defined in claim 3, wherein R1 is methyl.

### Claim 11 (depends on 1)

The 3-heterocyclyl-substituted benzoic acid compound of the formula III defined in claim 1, wherein R1 is methyl.

### Claim 12 (depends on 2)

The 3-heterocyclyl-substituted benzoic acid compound of the formula III defined in claim 2, wherein R1 is methyl.

### Claim 13 (depends on 3)

The 3-heterocyclyl-substituted benzoyl compound of the formula I defined in claim 3, wherein
X is O;
R1 is C1-C2-alkyl;
R2 is C1-C6-alkylthio or C1-C6-alkylsulfonyl;
R3 is hydrogen;
Y is CR13R14; and
R13, R14 are hydrogen or C1-C4-alkyl.

### Claim 14 (depends on 4)

The composition defined in claim 4, comprising a herbicidally active amount of at least one 3-heterocyclyl-substituted benzoyl compound of the formula I or of the agriculturally useful salt the formula of I, wherein
X is O;
R1 is C1-C2-alkyl;
R2 is C1-C4-alkylthio or C1-C6-alkylsulfonyl;
R3 is hydrogen;
Y is CR13R 14; and
R 13, R14 are hydrogen or C1-C4-alkyl.

### Claim 15 (depends on 1)

The 3-heterocyclyl-substituted benzoic acid compound of the formula III defined in claim 1, wherein
X is O;
R1 is C1-C2-alkyl;
R2 is C1-C6-alkylthio or C1-C6-alkylsulfonyl;
R3 is hydrogen;
Y is CR13R14; and
R13, R14 are hydrogen or C1-C4-alkyl.