Substituted N-aryl nitrogen-containing heterocyclic compounds

A substituted N-aryl nitrogen-containing heterocyclic compound of the general formula (I)

• 215
• in which
• Q1 represents oxygen or sulfer,
• Q2 represents oxygen or sulfur,
• R1 represents hydrogen, cyano or formyl or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkoxycarbonyl, alkenyl-oxycarbonyl or alkinyloxycarbonyl,
• R1 furthermore represents alkenyl or alkinyl, in each case optionally substituted by halogen,
• R1 furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
• R1 furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl,
• R2 represents hydrogen, cyano or formyl, or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,
• R2 furthermore represents alkenyl or alkenyl, in each case optionally substituted by halogen,
• R2 furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
• R2 furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl, and
• Ar represents the substituted monocyclic or bicyclic aryl or heteroaryl grouping defined below.
• 216
• in which
• R3 represents hydrogen or halogen,
• R4 represents hydrogen or halogen,
• R5 represents cyano, carboxyl, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl or halogen, or represents alkyl, alkoxy or alkoxycarbonyl, in each case optionally substituted by halogen,
• R6 represents the following grouping
• —A1—A2—A3
• in which
• A1 represents a single bond, or represents oxygen, sulfur, —SO—, —SO2—, —CO— or the grouping —N—A4—, in which A4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl,
• A1 furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
• A2 represents a single bond, or represents oxygen, sulfur, —SO—, —SO2—, —CO— or the grouping —N—A4—, in which A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
• A2 furthermore represents alkanediyl, alkenediyl, azaalkenediyl, akinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
• A3 represents hydrogen, with the proviso that in this case A1 and/or A2 do(es) not represent any single bond,
• A3 furthermore represents hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thio-carbamoyl, sulfo, chlorosulfonyl or halogen, or represents alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)-phosphoryl, in each case optionally substituted by halogen or alkoxy,
• A3 furthermore represents alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylthio, alkinylamino or alkinyloxycarbonyl, in each case optionally substituted by halogen,
• A3 furthermore represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, in each case optionally substituted by halogen, cyano, carboxyl, alkyl and/or alkoxy-carbonyl,
• A3 furthermore represents aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, in each case optionally substituted by nitro, cyano, carboxyl, halogen, alkyl, halogenalkyl, alkyloxy, halogenalkyloxy and/or alkoxy-carbonyl,
• A3 furthermore represents in each case optionally completely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy or furylalkoxy, or represents perhydropyranylalkoxy or pyridylalkoxy, and
• R7 represents hydrogen or halogen,
• or in each case two adjacent radicals—R3 and R4, R4 and R5, R5 and R6 or R6 and R7—together represent one of the following groupings
• —Q3—CQ4—, —Q3—CQ4—Q5—, —Q3—C(R8, R9)—Q5—, —C(R8, R9)—CQ4—, —C(R8, R9)—Q3—CQ4—, —Q3—C(R8, R9)—C(R8, R9)——Q3—C(R8, R9)—C(R8, R9)—Q5—, —C(R8, R9)—C(R8, R9)—CQ4—, —Q3—C(R8)═C(R8)—, —C(R8)═C(R8)—CQ4—, —Q3—(R8, R9)—CQ4—, —N(R10)—C(R8, R9)—CQ4—, —C(R8)═N—, —Q3—CQ4—C(R8, R9)—, —Q3—CQ4—N(R10)—, —Q3—C(R8, R9)—CQ4—N—(R10)—, —C(R8, R9)—Q3—CQ4—N(R10)—, —C(R8, R9)—C(R8, R9)—N(R10)—, —C(R8, R9)—C(R8, R9)—CQ4—N(R10)—, —C(R8)═C(R8)—N(R10)—, —C(R8)═C(R8)—, CQ4—N(R10)—, —C(R8, R9)—CQ4—N(R10)—, —N(R10)—C(R8, R9)—CQ4—N(R10)—, —C(R8)═N—N(R10)—, —Q3—CQ4—C(R8, R9)—N(R10)—, Q3—C(R8, R9)—C(R8, R9)—CQ4—N(R10)—
• m which
• Q3, Q4 and Q5 are identical or different and in each case represent oxygen or sulfur,
• R8 and R9 are identical or different and individually represent hydrogen, halogen or alkyl or together represent alkanediyl, and
• R10 represents hydrogen or hydroxyl, or represents alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl which are optionally substituted by cyano, halogen, alkoxy, alkylcarbonyl or alkoxy-carbonyl, or represents alkenyl or alkinyl, in each case optionally substituted by halogen, or represents cycloalkyl or cycloalkylalkyl, in each case optionally substituted by halogen or alkyl, or represents alkoxy or alkenyloxy, in each case optionally substituted by halogen, or represents arylalkyl or arylalkoxy, in each case optionally substituted by cyano, halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy,
• excluding the compounds 4-(3,4dichlorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and 4-(4-chloro-3-trifluoromethylphenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one.