2-(2-methylphenyl)-3,4-dihydro-2H-pyrrole derivatives

Compounds of the formula (I)

• in which
• Ar represents the radical
• in which
• m represents 0, 1, 2, 3 or 4,
• R1 represents hydrogen, F, Cl, Br, cyano, trialkylsilyl, —CO—NR4R5, tetrahydropyranyl or represents one of the following groupings
• (l) —X—A
• (m) —B—Z—D or
• (n) —Y—E,
• R2 represents hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkoxy or —S(O)OR3,
• with the proviso that R1 does not represent hydrogen if m=1 and R2=iodine,
• o represents 0, 1 or 2,
• R3 represents alkyl or halogenoalkyl,
• R4 and R5 independently of one another each represent hydrogen, alkyl, halogenoalkyl or represent phenyl or phenylalkyl, each of which is unsubstituted or mono- or polysubstituted by radicals from the list W1,
• X represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or dialkylsilylene,
• A represents phenyl, naphthyl or tetrahydronaphthyl, each of which is unsubstituted or mono- or polysubstituted by radicals from the list W1, or represents 5- to 10-membered heterocyclyl containing one or two aromatic rings and having one or more heteroatoms from the group consisting of nitrogen, oxygen and sulphur and being in each case unsubstituted or mono- or polysubstituted by radicals from the list W2,
• B represents p-phenylene which is unsubstituted or mono- or disubstituted by radicals from the list W1,
• Z represents oxygen or sulphur,
• D represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogeno-alkenyl, represents in each case unsubstituted or halogen-, alkyl-, alkenyl-, halogenoalkenyl, phenyl-, styryl-, halogenophenyl- or halogenostyryl-substituted cycloalkyl or cycloalkylalkyl;
• represents in each case unsubstituted or halogen- or alkyl-substituted cycloalkenyl or cycloalkenyl-alkyl;
• represents in each case unsubstituted or nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenylalkyl, naphthylalkyl, tetrahydronaphthylalkyl or hetarylalkyl having 5 or 6 ring members and one or two heteroatoms from the group consisting of nitrogen, oxygen and sulphur;
• represents —CO—R6, —CO—NR7R8 or represents the grouping
• —(CH2)p—(CR9R10)q—(CH2)rG
• or
• Z and D together represent unsubstituted or nitro-, halogen-, alkyl-, alkoxy-, halo-genoalkyl- or halogenoalkoxy-substituted phenoxyalkyl,
• Y represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or represents p-phenylene which is unsubstituted or mono- or disubstituted by radicals from the list W1,
• E represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogeno-alkenyl, represents in each case unsubstituted or halogen-, alkyl-, alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl- or halogeno-styryl-substituted cycloalkyl;
• represents in each case unsubstituted or halogen- or alkyl-substituted cycloalkenyl;
• represents phenyl which is unsubstituted or mono- to tetrasubstituted by radicals from the list W1 or represents 5- or 6-membered hetaryl having one or two heteroatoms from the group consisting of nitrogen, oxygen and sulphur and being in each case unsubstituted or mono- to tetrasubstituted by radicals from the list W2;
• or represents the grouping
• —(CH2)p—(CR9R10)q—(CH2)rG
• R6 represents alkyl, alkoxy, alkenyl, alkenyloxy, in each case optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyloxy or represents in each case optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or naphthyl,
• R7 represents hydrogen or alkyl,
• R8 represents alkyl, halogenoalkyl;
• represents in each case unsubstituted or halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl or cycloalkylalkyl;
• or represents in each case unsubstituted or halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or phenylalkyl,
• p, q and r independently of one another each represent 0, 1, 2 or 3, their sum being smaller than 6 and greater than 1,
• R9 and R10 independently of one another each represent hydrogen or alkyl,
• G represents cyano, represents an unsubstituted or halogen-, alkyl- or halogenoalkyl- and, at the point of linkage, optionally R11-substituted 5- or 6-membered heterocycle having 1 to 3 identical or different heteroatoms from the group consisting of nitrogen, oxygen and sulphur or one of the following groups
• (a) —CO—RL11
• (b) —CO—OR12
• (c) —CO—NR13R14
• (d) —CS—NR13R14
• R11 represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, represents unsubstituted or halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl;
• or represents phenyl which is unsubstituted or mono- to pentasubstituted by alkylcarbonylamino, alkylcarbonylalkylamino and/or radicals from the list W3,
• R12 represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl;
• represents in each case unsubstituted or halogen-, alkyl- or halogeno-alkyl-substituted cycloalkyl or cycloalkylalkyl or represents arylalkyl which is unsubstituted or mono- to pentasubstituted by radicals from the list W3,
• R13 and R14 independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, represent in each case unsubstituted or halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl, represent aryl or arylalkyl, each of which is unsubstituted or mono- to pentasubstituted by radicals from the list W3, represent —OR12 or —NR11R12 or together represent an alkylene chain having 2 to 6 members in which optionally one methylene group is replaced by oxygen,
• R15 represents —OR12, —NR11R12 or —N(R11)—COOR12,
• R16, R17 and R18 independently of one another each represent alkyl, W1 represents hydrogen, halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, alkyl carbonyl, alkoxycarbonyl, pentafluorothio or —S(O)OR3,
• W2 represents halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkylcarbonyl, alkoxycarbonyl, penta-fluorothio, —S(O)OR3 or —C(R11)=N—R15,
• W3 represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogeno-alkoxy, dialkylamino, —S(O)OR3, —COOR19 or —CONR20R21,
• R19 represents hydrogen, alkyl, halogenoalkyl, represents unsubstituted or halogen-, alkyl or halogenoalkyl-substituted cycloalkyl;
• or represents phenyl which is unsubstituted or mono- to pentasubstituted by radicals from the list W4,
• R20 and R21 independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, represent in each case unsubstituted or halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl;
• or represent aryl or arylalkyl, each of which is unsubstituted or mono- to pentasubstituted by radicals from the list W4, represent —OR16 or —NR17R18 or together represent an alkylene chain having 2 to 6 members in which optionally one methylene group is replaced by oxygen, and
• W4 represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, haiogeno-alkoxy, dialkylamino, alkoxycarbonyl, dialkylaminocarbonyl or —S(O)OR3.