Method for producing tetrazole-substituted anthranilic acid diamide derivatives by reacting pyrazolic acids with anthranilic acid esters

1. A process for preparing a compound of formula (I)

in which

R 1 , R 3 independently of one another represent hydrogen, or represent C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl which are each optionally mono- or polysubstituted by identical or different halogen or nitro substituents,

R 2 represents C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halogen, cyano, nitro, alkylamino, dialkylamino, cycloalkylamino or C 3 -C 6 -trialkylsilyl,

R 4 represents hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, SF 5 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 3 -C 6 -cycloalkylamino, (C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -alkyl)(C 1 -C 4 -alkoxy)imino, (C 1 -C 4 -haloalkyl)(C 1 -C 4 -cyano, nitro, alkoxy)imino or C 3 -C 6 -trialkylsilyl,

Q represents a tetrazole ring which is monosubstituted by R 5 ,

R 5 represents C 1 -C 5 -alkyl which may be mono- to trisubstituted by halogen,

Z represents CH or N,

Wherein the compound of formula (I) furthermore may also comprise an N-oxide and/or a salt,

comprising reacting a tetrazole-substituted pyrazole acid of formula (II)

with an anthranilic ester of formula (III)

in which

R represents alkyl, cycloalkyl, alkoxyalkyl, arylalkyl, thioalkyl, alkylthioalkyl, alkylsulphonylalkyl, cyanoalkyl, haloalkyl, nitroalkyl or aryl,

to give a compound of formula (IV)

and reacting said compound of formula (IV) with an amine of general formula (V)

R 1 NH 2   (V)

to give an anthranilamide of formula (I).

2. The process for preparing a compound according to claim 1 , wherein

R 1 , R 3 independently of one another represent (C 1 -C 5 )-alkyl,

R 2 represents halogen or C 1 -C 6 -alkyl,

R 4 represents hydrogen, chlorine or cyano,

Q represents a tetrazole ring which is monosubstituted by R 5 and selected from the group consisting of

R 5 represents (C 1 -C 3 )-perfluoroalkyl,

Z represents N.

3. The process for preparing a compound according to claim 1 , wherein

R 1 , R 3 independently of one another represent methyl, ethyl or tert-butyl,

R 2 represents fluorine or chlorine,

R 4 represents chlorine or cyano,

Q represents Q-1 or Q-2,

R 5 represents CF 3 or C 2 F 5 ,

Z represents N.

4. The process for preparing a compound according to claim 1 , wherein R 5 represents CF 3 .

5. The process for preparing a compound according to claim 1 , wherein R 2 represents chlorine, R 3 represents methyl and R 4 represents cyano.

6. The process for preparing a compound according to claim 1 , wherein a ratio of compound of formula (I) in which Q represents Q-1 to compound of formula (I) in which Q represents Q-2 is from 90:10 to 96:4.

7. The process for preparing a compound according to claim 1 , wherein reaction of a pyrazole acid of formula (II) with an anthranilic ester of formula (III) is carried out with addition of a base.

8. The process for preparing a compound according to claim 1 , wherein a compound of formula (IV) is reacted at a reaction temperature of from 0° C. to +100° C. with a compound of formula (V) to give an anthranilic acid diamide derivative of formula (I).