# US 2014/0194623 A1 · Process for preparing tetrazole-substituted anthranilic acid diamide derivatives by reacting benzoxazinones with amines

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- Number: US 2014/0194623 A1
- Document ID: US20140194623A1
- Status: Published application
- Kind: A1
- Application number: 14/240,224
- Filed: 2012-08-24
- Published: 2014-07-10
- Earliest claimed: 2011-08-26
- Assignees: Bayer Intellectual Property GmbH
- Inventors: Sergii Pazenok; Werner Lindner; Hartmut Scheffel
- Web page: https://patentgrep.com/patent/US20140194623A1

## CPC

- C07D 413/14: containing three or more hetero rings
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a process for preparing tetrazole-substituted anthranilic acid diamide derivatives of the formula (I) in which R1, R2, R3, R4, Q and Z have the meanings given in the description, by reacting benzoxazinones with amines.

## Claims

### Claim 1

Process for preparing a compound of formula (I)
in which
R1, R3 independently of one another represent hydrogen, or represent C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl which are each optionally mono- or polysubstituted by identical or different halogen or nitro substituents,
R2 represents C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halogen, cyano, nitro, alkylamino, dialkylamino, cycloalkylamino or C3-C6-trialkylsilyl,
R4 represents hydrogen, halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, SF5, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, C3-C6-cycloalkylamino, (C1-C4-alkoxy)imino, (C1-C4-alkyl) (C1-C4-alkoxy)imino, (C1-C4-haloalkyl)(C1-C4-cyano, nitro, alkoxy)imino or C3-C6-trialkylsilyl,
Q represents a tetrazole ring which is monosubstituted by R5, optionally a tetrazole ring which is monosubstituted by R5 and selected from the group consisting of
R5 represents C1-C5-alkyl which may be mono- to trisubstituted by halogen,
Z represents CH or N,
the compound of formula (I) furthermore may include an N-oxide and/or a salt thereof,
wherein said process comprises reacting a tetrazole-substituted pyrazole acid of formula (II)
with an isatoic anhydride of formula (III)
to give a compound of formula (IV)
and reacting said compound of formula (IV) in the presence of an acid with an amine of formula (V)
R1NH2 (V)
to give a compound of formula (I) and/or an N-oxide and/or a salt thereof.

### Claim 2 (depends on 1)

Process according to claim 1, wherein
R1, R3 independently of one another represent (C1-C5)-alkyl,
R2 represents halogen or C1-C6-alkyl,
R4 represents hydrogen, chlorine or cyano,
Q represents a tetrazole ring which is monosubstituted by R5 and selected from the group consisting of
R5 represents (C1-C3)-perfluoroalkyl,
Z represents N.

### Claim 3 (depends on 1)

Process according to claim 1, wherein
R1, R3 independently of one another represent methyl, ethyl or tert-butyl,
R2 represents fluorine or chlorine,
R4 represents chlorine or cyano,
Q represents Q-1 or Q-2,
R5 represents CF3 or C2F5,
Z represents N.

### Claim 4 (depends on 1)

Process according to claim 1, wherein R5 represents CF3.

### Claim 5 (depends on 1)

Process according to claim 1, wherein R2 represents chlorine, R3 represents methyl and R4 represents cyano.

### Claim 6 (depends on 1)

Process according to claim 1, wherein the ratio of compounds of the formula (I) in which Q represents Q-1 to compounds of the formula (I) in which Q represents Q-2 is from 90:10 to 96:4.

### Claim 7 (depends on 1)

Process according to claim 1, wherein, when the compound of formula (IV) is reacted with the compound of formula (V), from 0.001 to 1.5 mol of an organic and/or inorganic acid is added per 1 mol of compound of formula (IV).

### Claim 8 (depends on 1)

Process according to claim 1, wherein, when the compound of formula (IV) is reacted with the compound of formula (V), from 0.01 to 0.3 mol of CF3COOH is added per 1 mol of compound of formula (IV).

### Claim 9 (depends on 1)

Process according to claim 1, wherein the compound of formula (IV) is reacted at a reaction temperature of from 0° C. to +100° C. with the compound of formula (V) to give an anthranilic acid diamide derivative of formula (I) and/or an N-oxide and/or a salt thereof.