Patent DE-19822245-A1 (DE)
Title: New diphenylpyrrole derivatives useful for control of animal pests, e.g. in protection of plants, goods and materials and in veterinary medicine
Inventor: PLANT ANDREW
IPC: C07C271/18
Filed: 1998-05-18
Abstract: 2,5-Diphenyl-3,4-dihydro-2H-pyrrole derivatives (I) are new. Aminoketones (VIII) and nitroketones (XVIII) used in their preparation are also new. 2-(2-Methyl-phenyl)-5-phenyl)-3,4-dihydro-2H-pyrrole derivatives (I) are new: Ar = group of formula (a): m = 0-4; R<1> = H; F; Cl; Br; CN; (alkyl)3Si; CONR<4>R<5>; tetrahydropyranyl; -X-A; -B-Z-D; or -Y-E, but is not H when m = 1 and R<2> = H ; R<2> = H; halo; CN; NO2; alkyl, haloalkyl, alkoxy, haloalkoxy; alkoxyalkoxy; or -S(O)oR<3>; o = 0-2; R<3> = alkyl or haloalkyl; R<4> and R<5> = H; alkyl; haloalkyl; or phenyl or phenylalkyl optionally substituted with W<1>; X = direct bond; O; S; C(O); C(O)O; OC(O); alkylene; alkenylene; alkynylene; alkyleneoxy; oxyalkylene; thioalkylene; alkylenedioxy; or dialkylsilylene; A = phenyl, naphthyl or tetrahydronaphthyl optionally substituted with W<1>; or aromatic heterocyclyl optionally substituted with W<2>; B = p-phenylene optionally substituted with W<1>; Z = O or S; D = H; alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; cycloalkyl or cycloalkylalkyl optionally substituted with halo, alkyl or optionally ha lo-substituted alkenyl, phenyl or styryl; optionally halo- or alkyl-substituted cycloalkenyl or cycloalkenylalkyl; phenylalkyl, naphthylalkyl, tetrahydronaphthyl or heteroaryl optionally substituted with 6 groups; -C(O)R<6>; -C(O)NR<7>R<8>; or a group of formula (b): (CH2)p-(CR<9>R<10>)q-(CH2)r-G   (b) or Z and G together form phenoxyalkyl optionally substituted with 6 groups; Y = direct bond; O; S; C(O); C(O)O; OC(O); alkylene; alkenylene; alkynylene; alkyleneoxy; oxyalkylene; thioalkylene; alkylenedioxy; or p-phenylene optionally substituted with W<1>; E = H; alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; cycloalkyl optionally substituted with 8 groups; cycloalkenyl optionally substituted with halo or alkyl; phenyl optionally substituted with W<1>; heteroaryl optionally substituted with W<2>; or a group of formula (b); R<6> = alkyl; alkoxy; alkenyl; alkenyloxy; cycloalkyl, cycloalkyloxy or cycloalkylalkoxy optionally substituted with 5 groups; or phenyl or naphthyl optionally substituted with 6 groups; R<7> = H or alkyl; R<8> = alkyl; haloalkyl; or cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl optionally substituted with 5 groups; p, q and r = 0-3, (p + q + r is less than 6); R<9> and R<10> = H or alkyl; G = CN; heterocyclyl optionally substituted with halo, alkyl or haloalkyl and on the linkage site optionally with R<11>; -C(O)-R<11>; -C(O)-OR<12>; -C(Q)-NR<13>R<14>; -C(R<11>)=N-R<15>; -C(R<11>)(QR<16>)2; -C(R<11>)(NR<17>R<18>)(QR<16>); or -C(QR<18>)=N-R<17>; Q = O or S; R<11> = H; alkyl; alkenyl; haloalkyl; haloalkenyl; cycloalkyl optionally substituted with halo, alkyl or haloalkyl; or phenyl optionally substituted with alkylcarbonylamino, alkylcarbonylalkylamino and/or W<3>; R<12> = H; alkyl; alkenyl; haloalkyl; haloalkenyl; cycloalkyl or cycloalkylalkyl optionally substituted with halo, alkyl or haloalkyl; or arylalkyl optionally substituted with W<3>; R<13> and R<14> = H; alkyl; alkenyl; haloalkyl; haloalkenyl; alkoxy; cycloalkyl or cycloalkylalkyl optionally substituted with halo, alkyl or haloalkyl; aryl or arylalkyl optionally substituted with W<3>; OR<12>; or NR<11>R<12>; or R<13> and R<14> together form alkylene with 1 CH2 optionally replaced with O; R<15> = -OR<12>; -NR<11>R<12>; or -N(R<11>)-COOR<12>; R<16>, R<17> and R<18>  = alkyl; W<1> = H; halo; CN; CHO; NO2; alkyl; (alkyl)3Si; alkoxy; haloalkyl; haloalkoxy; haloalkenyloxy; alkylcarbonyl; alkoxycarbonyl; pentafluorothio; or -S(O)oR<3>; W<2> = halo; CN; CHO; NO2; alkyl; (alkyl)3Si; alkoxy; haloalkyl; haloalkoxy; alkylcarbonyl; alkoxycarbonyl; pentafluorothio; -S(O)oR<3>; or -C(R<11>)=N-R<15>; W<3> = halo; CN; NO2; alkyl; alkoxy; haloalkyl; haloalkoxy; -N(alkyl)2; -S(O)oR<3>; -COOR<19>; or -CONR<20>R<21>; R<19> = H; alkyl; haloalkyl; cycloalkyl optionally substituted with halo, alkyl or haloalkyl; or phenyl optionally substituted with W<4>; R<20> and R<21> = H; alkyl; alkenyl; haloalkyl; haloalkenyl; alkoxy; cycloalkyl or cycloalkylalkyl optionally substituted with halo, alkyl or haloalkyl; aryl or arylalkyl optionally substituted with W<4>; OR<16>; or -NR<17>R<18>; or R<20> and R<21> together form alkylene with 1 CH2 optionally replaced with O; W<4> = H; halo; CN; NO2; alkyl; alkoxy; haloalkyl; haloalkoxy; -N(alkyl)2; alkoxycarbonyl; dialkylaminocarbonyl; or -S(O)oR<3>. The full definitions are given in the DEFINITIONS (Full Definitions) field. Independent claims are also included for: (a) the preparation of compounds (I); (b) aminoketone intermediates of formula (VIII); and (c) nitroketone intermediates of formula (XVIII).