Patent EP-0637298-B1 (EP)
Inventor: KLINTZ RALF
IPC: C07C255/46
Filed: 1993-04-20
Granted: 1999-03-31
Abstract: Substd. cyclohexene-1,2-dicarboxylic acid derivs. of formula (I), and their salts are new. Where T = CONR1R2 or CN; R1, R2 = H; R, 3-6C alkenyl, or 3-6C alkynyl, all opt. substd. by 1-3 halo, CN, NH2, SH, OH, OR, RSO, RSO2, RCO, COOH, ROCO, RNH, (R)2N, RNHCO, (R)2NCO, (RO)(HO)PO, (RO)2PO, or Ar); or Ar' when R1 is H or R, R2 may also be OH, RO, 3-6C alkenyloxy, 3-6C alkynyloxy, 3-7C cycloalkoxy 5-7 cycloalkenyloxy, 1-6C haloalkoxy, 3-6C halo alkenyloxy, 3-7C cycloalkyl-1-6C alkoxy, RCOO, 1-6C cyanoalkoxy, etc.; NR1R2 = a 3-8 membered non-aromatic heterocycle contg. 1-3N atoms and/or one O or S atom and opt. 1-2 CO gps., the ring being opt. substd. by 1-3R; Ar = phenyl or a 3-8 membered heterocycle (contg. 1-4 heteroatoms selected from 1-4N, 1O or 1S) both opt. substd. on every substitutable atom by OH, halo, CN, NO2, CF3, R or RO; Ar' as Ar except that the heterocycle contains 1-4 heteroatoms selected from 1-4N, 1-20 and 1-2S, and only C-atoms may be substd. R = 1-6C alkyl; R3 = H or R; R4 = H or halo; R5 = H, halo, NO2, CN or CF3; R6 = a 3-8 membered heterocycle (contg. 1-4 heteroatoms selected from 1-4N, 1-2O and 1-2S, and in which 1-2 CH2 gps. are opt. replaced by CO), opt. C-substd. by R, 2-6C alkenyl, 2-6C alkynyl, RO, RS, 3-6C alkenyloxy, 3-6C alkynyloxy, 3-6C alkenylthio, 3-6C alkynylthio, ROCO, NO2, NH2, halo, 1-4C alkylamino, di(1-4C)alkylamino, CN, 1-6C cyanoalkyl, 1-6C haloalkyl or 1-6C haloalkyloxy; ACN, ACOB, OR9, C(O)R10, C(S)R10, C(NR16)R10, A = straight chain 2-4C alkenylene or 2-4C alkynylene, both opt. substd. by 1-2 halo, CN, R, 1-6C haloalkyl, OH, RO, RCOO, ROCO or RCO; B = H, R, 3-6C alkenyl, 3-6C alkynyl, 1-6C haloalkyl, 3-7C cycloalkyl, OR17, SR17, phenyl (opt. substd. by 1-3R, 2-6C alkenyl, halo, CN, NO2, 1-6C haloalkyl, RO or ROCO), 1-6C alkoxy-1-6C alkyl, di(1-6C alkoxy)-1-6C alkyl, 1-6C alkylthio-1-6C alkyl or NR18R19; R17 = H, R, 3-6C alkenyl, 3-6C alkynyl, 3-6C cycloalkyl, 1-6C haloalkyl, 1-6C cyanoalkyl, 3-6C haloalkenyl, ROCO, 1-6C alkoxy(1-6C)alkyl, 1-6C alkoxycarbonyl (1-6C) alkyl, 1-6C alkoxyimino(1-6C)alkyl, or phenyl (opt. substd. by 1-3 R, 2-6C alkenyl, halo, CN, NO2, 1-6C haloalkyl, RO or ROCO); R18, R19 = H, R, 3-6C alkenyl, 3-6C alkynyl, 3-6C cycloalkyl, 1-6C haloalkyl, RCO, ROCO, 1-6C alkoxy (1-6C)alkyl, or phenyl (opt. substd. by 1-3R, 3-6C alkenyl, halo, CN, NO2, RO or ROCO); R9 = 1-6C cyanoalkyl RQ, 1-6C haloalkyl, 3-6C haloalkenyl, 3-6C alkynyl, 3-6C haloalkynyl, 1-6 alkoxycarbonyl-2-6C alkyl, ROQOCOQ, 1-6C alkoxyimino (1-6C)alkyl, or phenyl, phenyl-Q, 3-8 membered heterocyclyl or heterocyclyl-Q (where the heterocycles contain 1-4 heteroatoms, etc.; R10 = H, CN, R, 3-6C alkenyl, 3-6C alkynyl, 1-6C haloalkyl, 3-7C cycloalkyl, ROCO, ROCOQ, or phenyl (opt. substd. by 1-3 halo, CN, NO2, R, 3-6C alkenyl, 1-6C haloalkyl, RO or ROCO); R16 = H, R, 3-6C alkenyl, 3-6C alkynyl, 3-7C cycloalkyl, 1-6C haloalkyl, phenyl (opt. substd. by 1-3R, halo, CN, 2-6C alkenyl, NO2, 1-6C haloalkyl, 1-6C alkoxy, or ROCO), ROQ, OH, RO, 3-6C alkenyloxy, 3-6C alkynyloxy, 5-7C cycloalkoxy, 5-7C cycloalkenyloxy, etc.; R5+R6 = an opt. unsatd. 3-5 membered carbon chain which opt. contains 1-2O, S, N, CO or 1-6C alkoximino gps. and which is opt. substd. by 1-2 CN, NO2, NH2, halo, R, 1-6C haloalkyl, 2-6C alkenyl, 2-6C alkynyl, 1-6C cyanoalkyl, RCOQ, phenyl-Q or 3-8 membered heterocyclyl-1-6C alkyl, where the heterocycle is opt. unsatd. and contains 1-4 heteroatoms selected from 1-4N, 1-20 and 1-2S; provided that when T is CONR1R2 then R9 is not 3-6C alkynyl and R16 is not 1-6C alkoxy, and when T is CN then R9 is not 1-6C haloalkoxy.