Patent DE-19929259-A1 (DE)
Title: New cyclohexanone derivatives of bicyclic benzoic acids useful as herbicides
Inventor: OTTEN MARTINA
IPC: C07D333/72
Filed: 1999-06-25
Abstract: Cyclohexanone derivatives of bicyclic benzoic acids (I) are new Cyclohexanone derivatives of bicyclic benzoic acids of formula (I) and their salts are new. X  = O, S, SO, SO2, NR<1> or NR<1>R<17>; R<1>  = H, 1-6C (halo)alkyl, (halo)alkoxy, (halo)alkyl sulfonyl or (halo)alkyl carbonyl, 1-6C alkoxy-1-6C alkyl, 1-6C alkylcarbonyl-1-6C alkyl(carbonyl), 1-6C alkylcarbonyloxy-1-6C alkyl, 3-6C cycloalkyl(carbonyl), 3-6C cycloalkoxy, 3-6C cycloalkyl(carbonyl(oxy))-1-6C alkyl, 3-6C cycloalkoxy(carbonyl(oxy))-1-6C alkyl, 3-6C cycloalkyl sulfonyl, phenyl(sulfonyl), phenyl carbonyl, phenyl-1-6C alkyl(carbonyl), phenyl(oxy)carbonyl-1-6C alkyl, phenoxy-1-6C alkyl, phenylcarbonyloxy-1-6C alkyl, heterocyclyl(-1-6C alkyl), heterocyclylsulfonyl, heterocyclylcarbonyl(oxy)-1-6C alkyl or heterocyclylcarbonyl(1-6C alkyl), where the phenyl, heterocyclyl or cycloalkyl can be substituted by 1-4C (halo)alkyl, (halo)alkoxy, (halo)alkyl carbonyl or (halo)alkyl sulfonyl, nitro, hydroxy or cyano and/or are halogenated;  R<2>  = halo, 1-6C (halo)alkylthio, (halo)alkylsulfinyl or (halo)alkylsulfonyl;  R<3>  = H, halo or 1-6C (halo)alkyl;  Hex  = substituted (3-oxo-1 -cyclohexene-2-yl)carbonyl of formula (i), substituted (1,3-dioxo-2-cyclohexyl)methylidene of formula (ii); or 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl (all optionally substituted with 1-3 1-4C alkyl); R<4>  = OH, SH, halo, OR<11>, SR<11>, SOR<12>, SO2R<12>, OSO2R<12>, P(O)R<13>R<14>, OP(O)R<13>R<14>, P(S)R<13>R<14>, OP(S)R<13>R<14>, NR<15>R<16>, ONR<15>R<16>, N-bound heterocycle optionally halogenated and/or substituted by 1-3 NO2, CN or 1-4C (halo)alkyl or (halo)alkoxy;  R<5>, R<9>  = H or 1-4C alkyl or alkoxycarbonyl; R<6>, R<8>, R<10>  = H or 1-4C alkyl; or R<6> + R<8>, R<8> + R<10> = a bond or 1-5C alkyl (optionally substituted with 2 or 3 halo, CN, 1-4C (halo)alkyl or alkoxycarbonyl); or R<6> + R<10> = 1-4C alkyl (optionally substituted with 2 or 3 halo, CN or 1-4C (halo)alkyl or alkoxycarbonyl); R<7>  = H, OH, halo, 1-6C (halo)alkyl, (halo)alkoxy, (halo)alkylthio, (halo)alkylsulfinyl, (halo)alkylsulfonyl or (halo)alkoxycarbonyl, di-(1-6C alkoxy)methyl, (1-6C alkoxy)-(1-6C alkylthio)-methyl or di(1-6C alkylthio)methyl; or R<7> + R<8> = O(CH)2)pO, O(CH2)pS, S(CH2)pS, O(CH2)q or S(CH2)q (optionally substituted with 1-3 of halo, CN or 1-4C (halo)alkyl or alkoxycarbonyl); or carbonyl; p = 2-5; q = 2-6; R<11> = 1-6C alkyl(carbonyl), alkylthiocarbonyl or alkylaminocarbonyl, 3-6C (halo)alkenyl, (halo)alkynyl, cycloalkyl(carbonyl), alkenyloxycarbonyl, alkylnyloxycarbonyl, alkenylaminocarbonyl or alkynylaminocarbonyl-2-6C alkenylcarbonyl or alkylnylcarbonyl, N,N-di(1-6C alkyl)amino(thio)carbonyl, N-(3-6C alkenyl)-N-(1-6C alkyl)-aminocarbonyl, N-(3-6C alkynyl)-N-(1-6C alkyl)aminocarbonyl, N-(1-6C alkoxy)-N-(1-6C alkyl)aminocarbonyl, , N-(3-6C alkenyl)-N-(1-6C alkoxy)aminocarbonyl, N-(3-6C alkynyl)-N-(1-6C alkoxy)aminocarbonyl or 2-6C alkoxyimino-1-6C alkyl, the (cyclo)alkyl or alkoxy optionally having 2 or 3 of CN, 1-4C alkoxy, alkylthio, alkylcarbonyl or alkoxycarbonyl, di-(1-4C alkyl)amino(carbonyl), 1-4C alkoxy-1-4C alkoxycarbonyl, hydroxycarbonyl, 1-4C alkylaminocarbonyl, aminocarbonyl, 1-4C alkylcarbonyloxy or 3-6C cycloalkyl, phenyl(1-6C alkyl), phenyl(amino)carbonyl, phenoxy(thio)carbonyl, phenylcarbonyloxy-1-6C alkyl, N-(1-6C alkyl)-N-phenylaminocarbonyl, phenyl-2-6C alkenylcarbonyl, heterocyclyl(-1-6C alkyl), heterocyclylcarbonyl, heterocyclyloxy(thio)carbonyl, N-(1-6C alkyl)-N-heterocyclylaminocarbonyl or heterocyclyl-1-6C alkenylcarbonyl, where the phenyl or heterocyclyl can be substituted by NO2, CN, 1-4C (halo)alkyl or (halo)alkoxy; R<12> = 1-6C (halo)alkyl or 1-4C (halo)alkoxy optionally halogenated and/or with 2 or 3 of CN, 1-4C (halo)alkoxy, (halo)alkylthio, alkyl carbonyl or (halo)alkoxycarbonyl, phenyl(1-4C alkyl) or heterocyclyl(1-4C alkyl), the phenyl or heterocycle being optionally halogenated and/or with 2 or 3 of NO2, CN, 1-4C (halo)alkyl, (halo)alkoxy or alkyl carbonyl; R<13>, R<14> = phenyl(1-4C alkyl), phenoxy (both optionally halogenated and/or optionally substituted with 2 or 3 of NO2, CN, 1-4C (halo)alkyl, (halo)alkoxy or alkyl carbonyl), H, 1-6C alkyl(thio) or alkoxy; R<15> = H, 1-6C alkyl(carbonyl), alkoxy or alkylcarbonylamino, 3-6C (halo)alkenyl, cycloalkyl, alkenyloxy, alkynyloxy or (halo)alkynyl, amino, OH or di(1-6C alkyl)amino (the (cycloalkyl) or alkoxy being optionally halogenated and/or optionally substituted with 1-3 of CN, 1-4C alkoxycarbonyl or alkylaminocarbonyl, di-(1-4C alkyl)aminocarbonyl or 3-6C cycloalkyl), phenyl(1-4C alkyl), phenylcarbonyl, heterocyclyl(1-4C alkyl) or heterocyclylcarbonyl (the phenyl and heterocyclyl being optionally halogenated and/or optionally substituted with 1-3 of NO2, CN, 1-4C (halo)alkyl or (halo)alkoxy); and R<16>, R<17> = H, 1-6C alkyl or 3-6C alkenyl or alkynyl. An Independent claim is included for compounds as above but where Hex is replaced by COOH.