Phenyl-Substituted Bicyclooctane-1,3-Dione-Derivatives

A compound of formula (II)

• in which
• if
• Q represents a bond, a C1-C3-alkylene, a C2-C3-alkenylene or a C2-C3-alkynylene chain,
• then
• Y represents the groups —OR6, —S(O)pR6, —CO2R7, —CH═CH2, cyano, —SCN, —CONR8R9, —SO2NR8R9, —CR10═O, —NR11R12, —CR10═N—OR13, —CR10═N—R14, CR10═N—NR15R16, —CR10(OR17OR18), —CR10(SR17OR18), —CR10(SR17SR18), —CR10(NHR17NHR18), —CR10(NHR17OR18), —CR10(NHR17SR18), —CH(CN)2, —CH(OH)R6, halogen, —O(C=M)R10, —S(C=M)R10, —O(C=M)NR11R12, —S(C=M)NR11R12, —NH(C=M)NR11R12, —O(C=M)OR7, —S(C=M)OR7, —NH(C=M)OR7 or represents the group W,
• or Q, Y and R5 together form one of the groups CHCN═, CH(CO2C1-C6-alkyl)=,
• W represents a 3- to 7-membered saturated or partially saturated heterocycle which contains at least one heteroatom optionally oxygen, sulphur or nitrogen and may additionally be mono- or polysubstituted by identical or different substituents,
• G represents hydrogen, methyl, ethyl or benzyl (a) or represents one of the groups
• E represents a metal ion equivalent, a tertiary sulphonium ion or an ammonium ion,
• L represents oxygen or sulphur,
• M represents oxygen or sulphur,
• R1 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl or halo-C1-C3-alkylsulphonyl,
• R2 and R3 independently of one another are identical or different and represent hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl, halo-C1-C3-alkylsulphonyl, phenyl or phenyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl, halo-C1-C4-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, nitro and cyano,
• R4 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, or halo-C3-C6-cycloalkoxy,
• R5 represents hydrogen or C1-C4-alkyl,
• R6 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, halo-C3-C4-cycloalkoxy-C1-C4-alkyl, represents benzyl, phenyl, heteroaryl, —CH2—heteroaryl, —CH2CH2-heteroaryl, pyranyl, tetrahydrofuranyl, C1-C4-alkanoyl, halo-C1-C4-alkanoyl, benzoyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxyalkyl, halo-C1-C4-alkoxy-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl and halo-C3-C6-cycloalkoxy-C1-C6-alkyl, or represents benzoyl, which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl and halo-C3-C6-cycloalkyl,
• R7 represents hydrogen, represents in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or represents a cation E,
• R8 and R9 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R8 and R9 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R10 represents hydrogen, C1-C6-alkyl, halo-C1-C4-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, represents phenyl or benzyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C6-alkyl and halo-C1-C6-alkyl,
• R11 and R12 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R11 and R12 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R13 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, each of which is optionally interrupted at least once by oxygen or sulphur and is optionally mono- or polysubstituted by halogen, represents benzyl or —CH2-heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl,
• R14 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, phenyl, benzyl or represents phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C3-alkyl, halo-C1-C3-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, nitro and cyano,
• R15 and R16 independently of one another are identical or different and represent hydrogen, C1-C5-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R15 and R16 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R17 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R18 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R19 represents optionally halogen-substituted C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4alkyl, C1-C3-alkylthio-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or represents C3-C6-cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy and may optionally be interrupted in the ring by oxygen or sulphur, represents phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, each of which is optionally substituted by halogen or C1-C4-alkyl,
• R20 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, or represents C3-C6-cycloalkyl which may optionally be interrupted in the ring by oxygen or sulphur, or represents benzyl,
• R21, R22 and R23 independently of one another are identical or different and represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6 alkylamino, C1-C6 dialkylamino, C1-C3-alkylthio, C2-C4-alkenylthio, C3-C6-cycloalkylthio, each of which is optionally mono- or polysubstituted by identical or different halogen, or represent phenyl, benzyl, phenoxy or phenylthio,
• R24 and R25 independently of one another are identical or different and represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, represent phenyl or benzyl, optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl or
• R24 and R25 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• p represents the number 0, 1 or 2,
• or if
• Q, Y and R5 together represent the group CH2═, then
• G represents methyl, ethyl or benzyl (a),
• and
• R26 represents alkyl.

A compound of formula (XIII)

• in which
• if
• Q represents a bond, a C1-C3-alkylene, a C2-C3-alkenylene or a C2-C3-alkynylene chain,
• then
• Y represents the groups —OR6, —S(O)pR6, —CO2R7, —CH═CH2, cyano, —SCN, —CONR8R9, —SO2NR8R9, —CR10═O, —NR11R12, —CR10═N—OR13, —CR10═N—R14, CR10═N—NR15R16, —CR10(OR17OR18), —CR10(SR17OR18), —CR10(SR17SR18), —CR10(NHR17NHR18), —CR10(NHR17OR18), —CR10(NHR17SR18), —CH(CN)2, —CH(OH)R6, halogen, —O(C=M)R10, —S(C=M)R10, —O(C=M)NR11R12, —S(C=M)NR11R12, —NH(C=M)NR11R12, —O(C=M)OR7, —S(C=M)OR7, —NH(C=M)OR7 or represents the group W,
• or Q, Y and R5 together form one of the groups CHCN═, CH(CO2C1-C6-alkyl)=,
• W represents a 3- to 7-membered saturated or partially saturated heterocycle which contains at least one heteroatom optionally oxygen, sulphur or nitrogen and may additionally be mono- or polysubstituted by identical or different substituents,
• G represents hydrogen, methyl, ethyl or benzyl (a) or represents one of the groups
• E represents a metal ion equivalent, a tertiary sulphonium ion or an ammonium ion,
• L represents oxygen or sulphur,
• M represents oxygen or sulphur,
• R1 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl or halo-C1-C3-alkylsulphonyl,
• R2 and R3 independently of one another are identical or different and represent hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl, halo-C1-C3-alkylsulphonyl, phenyl or phenyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl, halo-C1-C4-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, nitro and cyano,
• R4 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6 alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, or halo-C3-C6-cycloalkoxy,
• R5 represents hydrogen or C1-C4-alkyl,
• R6 represents hydrogen, C1-C6-alkyl, halo-C1-C6 alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, halo-C1-C4-alkoxy-C1-C4 alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, halo-C3-C4-cycloalkoxy-C1-C4-alkyl, represents benzyl, phenyl, heteroaryl, —CH2—heteroaryl, —CH2CH2-heteroaryl, pyranyl, tetrahydrofuranyl, C1-C4-alkanoyl, halo-C1-C4-alkanoyl, benzoyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6 alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxyalkyl, halo-C1-C4 alkoxy C1-C6 alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl and halo-C3-C6-cycloalkoxy-C1-C6-alkyl, or represents benzoyl, which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6 alkyl, C3-C6-cycloalkyl and halo-C3-C6-cycloalkyl,
• R7 represents hydrogen, represents in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or represents a cation E,
• R8 and R9 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R8 and R9 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R10 represents hydrogen, C1-C6-alkyl, halo-C1-C4 alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, represents phenyl or benzyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C6-alkyl and halo-C1-C6-alkyl,
• R11 and R12 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R11 and R12 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R13 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, each of which is optionally interrupted at least once by oxygen or sulphur and is optionally mono- or polysubstituted by halogen, represents benzyl or —CH2-heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl,
• R14 represents hydrogen, C1-C6-alkyl, halo-C1-C6 alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, phenyl, benzyl or represents phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C3-alkyl, halo-C1-C3 alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, nitro and cyano,
• R15 and R16 independently of one another are identical or different and represent hydrogen, C1-C5-alkyl, C2-C6-alkenyl, C2-C6-alkenyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R15 and R16 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R17 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R18 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R19 represents optionally halogen-substituted C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4alkyl, C1-C3-alkylthio-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or represents C3-C6-cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy and may optionally be interrupted in the ring by oxygen or sulphur, represents phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, each of which is optionally substituted by halogen or C1-C4-alkyl,
• R20 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, or represents C3-C6-cycloalkyl which may optionally be interrupted in the ring by oxygen or sulphur, or represents benzyl,
• R21, R22 and R23 independently of one another are identical or different and represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C3-alkylthio, C2-C4-alkenylthio, C3-C6-cycloalkylthio, each of which is optionally mono- or polysubstituted by identical or different halogen, or represent phenyl, benzyl, phenoxy or phenylthio,
• R24 and R25 independently of one another are identical or different and represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, represent phenyl or benzyl, optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl or
• R24 and R25 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• p represents the number 0, 1 or 2,
• or if
• Q, Y and R5 together represent the group CH2═, then
• G represents methyl, ethyl or benzyl (a).

A compound of formula (XIV)

• in which
• if
• Q represents a bond, a C1-C3-alkylene, a C2-C3-alkenylene or a C2-C3-alkynylene chain,
• then
• Y represents the groups —OR6, —S(O)pR6, —CO2R7, —CH═CH2, cyano, —SCN, —CONR8R9, —SO9NR8R9, —CR10═O, —NR11R12, —CR10═N—OR13, —CR10═N—R14, CR10═N—NR15R16, —CR10(OR17OR18)—CR10(SR17OR18)—CR10(SR17SR18), —CR10(NHR17NHR18), —CR10(NHR17OR18), —CR10(NHR17SR18), —CH(CN)2, —CH(OH)R6, halogen, —O(C=M)R10, —S(C=M)R10, —O(C=M)NR11R12, —S(C=M)NR11R12, —NH(C=M)NR11R12, —O(C=M)OR7, —S(C=M)OR7, —NH(C=M)OR7 or represents the group W,
• or Q, Y and R5 together form one of the groups CHCN═, CH(CO2C1-C6-alkyl)=,
• W represents a 3- to 7-membered saturated or partially saturated heterocycle which contains at least one heteroatom optionally oxygen, sulphur or nitrogen and may additionally be mono- or polysubstituted by identical or different substituents,
• G represents hydrogen, methyl, ethyl or benzyl (a) or represents one of the groups
• E represents a metal ion equivalent, a tertiary sulphonium ion or an ammonium ion,
• L represents oxygen or sulphur,
• M represents oxygen or sulphur,
• R1 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl or halo-C1-C3-alkylsulphonyl,
• R2 and R3 independently of one another are identical or different and represent hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkyl,
• C2-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl, halo-C1-C3-alkylsulphonyl, phenyl or phenyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl, halo-C1-C4-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, nitro and cyano,
• R4 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, or halo-C3-C6-cycloalkoxy,
• R5 represents hydrogen or C1-C4-alkyl,
• R6 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, halo-C3-C4-cycloalkoxy-C1-C4-alkyl, represents benzyl, phenyl, heteroaryl, —C2—-heteroaryl, —CH2CH2-heteroaryl, pyranyl, tetrahydrofuranyl, C1-C4-alkanoyl, halo-C1-C4-alkanoyl, benzoyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxyalkyl, halo-C1-C4-alkoxy-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl and halo-C3-C6-cycloalkoxy-C1-C6-alkyl, or represents benzoyl, which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl and halo-C3-C6-cycloalkyl,
• R7 represents hydrogen, represents in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or represents a cation E,
• R8 and R9 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R8 and R9 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R10 represents hydrogen, C1-C6-alkyl, halo-C1-C4 alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, represents phenyl or benzyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C6-alkyl and halo-C1-C6-alkyl,
• R11 and R12 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R11 and R12 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R13 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, each of which is optionally interrupted at least once by oxygen or sulphur and is optionally mono- or polysubstituted by halogen, represents benzyl or —CH2-heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl,
• R14 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, phenyl, benzyl or represents phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C3-alkyl, halo-C1-C3-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, nitro and cyano,
• R15 and R16 independently of one another are identical or different and represent hydrogen, C1-C5-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
• R15 and R16 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• R17 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R18 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
• R19 represents optionally halogen-substituted C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4alkyl, C1-C3-alkylthio-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or represents C3-C6-cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy and may optionally be interrupted in the ring by oxygen or sulphur, represents phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, each of which is optionally substituted by halogen or C1-C4-alkyl,
• R20 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, or represents C3-C6-cycloalkyl which may optionally be interrupted in the ring by oxygen or sulphur, or represents benzyl,
• R21, R22 and R23 independently of one another are identical or different and represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C3-alkylthio, C2-C4-alkenylthio, C3-C6-cycloalkylthio, each of which is optionally mono- or polysubstituted by identical or different halogen, or represent phenyl, benzyl, phenoxy or phenylthio,
• R24 and R25 independently of one another are identical or different and represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, represent phenyl or benzyl, optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl or
• R24 and R25 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
• p represents the number 0, 1 or 2,
• or if
• Q, Y and R5 together represent the group C2═, then
• G represents methyl, ethyl or benzyl (a)
• R26 represents alkyl or hydrogen,
• R33 represents alkyl.