Patent DE-102004054666-A1 (DE)
Title: New substituted pyrazol-3-carboxamide derivatives useful to combat harmful plants and for growth regulation of plants
Inventor: JAKOBI HARALD
IPC: C07D231/56
Filed: 2004-11-12
Abstract: Substituted pyrazol-3-carboxamide derivatives (I) and their salts are new. Substituted pyrazol-3-carboxamide derivatives of formula (I) and their salts are new. R1>, R2>(1-6C) alkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (3-6C)-cycloalkyl, (1-6C)-alkoxy, (3-6C)-cycloalkoxy, (1-6C)-alkanoyl, (1-6C)-alkenylcarbonyl, (2-6C)-alkynylcarbonyl, (1-6C)-alkoxycarbonyl, di-((1-6C)-alkyl)-amino-(1-6C)-alkyl, di-((1-6C)-alkyl)-amino-(1-6C)-alkenyl, di-((1-6C)-alkyl)-amino-carbonyl (all optionally substituted with halo or CN), 6-14C aryl, 4-7C heterocyclyl containing one or more N, O and/or S (both optionally substituted by T), or H; or R1>R2>condensed 8-12C carbocycle or heterocycle containing O, S and/or N (optionally substituted with T, NO2, (3-6C)-halocycloalkyl, 6-14C aryl (optionally substituted with T) or 4-7C heterocyclyl containing one or more N, O and/or S (optionally substituted with T); T : halo, CN, (1-6C)-alkyl, (1-6C)-haloalkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (3-6C)-cycloalkyl, (3-6C)-cycloalkenyl, mono-(1-6C)-alkylamino, di-((1-6C)-alkyl)-amino, N-(1-6C)-alkanoyl)-amino, (1-6C)-alkoxy, (1-6C)-haloalkoxy, (2-6C)-alkenyloxy, (2-6C)-alkynyloxy, (3-9C)-cycloalkoxy, (5-9C)-cycloalkenyloxy, (1-6C)-alkylthio, (3-9C)-cycloalkylthio, (2-6C)-alkenylthio, (5-9C)-cycloalkenylthio, (2-6C)-alkynylthio, (1-6C)-alkanoyl, (2-6C)-alkenylcarbonyl, (2-6C)-alkynylcarbonyl, arylcarbonyl, (1-6C)-alkoxycarbonyl, (2-6C)-alkenyloxycarbonyl, (2-6C)-alkynoxycarbonyl, aryloxycarbonyl, (1-6C)-alkylsulfinyl or (1-6C)-alkylsulfonyl; R3>(1-6C)-alkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (2-3C)-heterocycloalkyl, arylalkyl, (3-6C)-cycloalkyl, (3-6C)-cycloalkenyl, (1-6C)-alkylsulfinyl (all optionally substituted with halo, (1-6C)-alkoxy, (1-6C)-alkylthio or CN), H, -C(O)X or -(SO2)Y; X, Y : (1-6C)-alkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (3-6C)-cycloalkyl, (3-6C)-cycloalkenyl, mono-(1-6C)-alkylamino, di-((1-6C)-alkyl)-amino, N-(1-6C)-alkanoyl)-amino, (1-6C)-alkoxy, (2-6C)-alkenyloxy, (2-6C)-alkynyloxy, (3-9C)-cycloalkoxy, (5-6C)-cycloalkenyloxy (all optionally substituted with halo, CN or NO2), 6-14C aryl (optionally substituted with T) or 4-7C heterocyclyl containing one or more N, O and/or S (optionally substituted with T); and either R4>(1-6C)-alkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (3-6C)-cycloalkyl, (3-6C)-cycloalkenyl (all optionally substituted with halo, NO2, CN, (3-6C)-cycloalkyl, (1-6C)-alkoxy, (1-6C)-haloalkoxy or (1-6C)-alkylthio), benzyl or H; R5>(1-6C)-alkyl or (1-6C)-alkenyl (optionally substituted with halo, NO2, OH, CN, NH2, (1-6C)-alkoxy, (1-6C)-alkoxycarbonyl, (1-6C)-haloalkoxy or (1-6C)-alkylthio), 6-14C aryl (optionally substituted with T1>), 4-7C heterocyclyl containing one or more N, O and/or S (optionally substituted with T1>) or bicyclic group formed by two overlapping alkoxy or alkylthio groups (optionally substituted by T2>); or R4>+R5>4-10C carbocycle or heterocycle containing one or more O, S and/or N (optionally substituted with halo, NO2, CN or (1-6C)-alkyl); T1>halo, CN, (1-6C)-alkyl, (2-6C)-alkenyl, (2-6C)-alkynyl, (3-6C)-cycloalkyl, (3-6C)-cycloalkenyl, mono-(1-6C)-alkylamino, di-((1-6C)-alkyl)-amino, N-(1-6C)-alkanoyl)-amino, (1-6C)-alkoxy, (2-6C)-alkenyloxy, (2-6C)-alkynyloxy, (3-9C)-cycloalkoxy, (5-9C)-cycloalkenyloxy, (1-6C)-alkylthio, (3-9C)-cycloalkylthio, (2-6C)-alkenylthio, (5-9C)-cycloalkenylthio, (2-6C)-alkynylthio, (1-6C)-alkanoyl, (2-6C)-alkenylcarbonyl, (2-6C)-alkynylcarbonyl, arylcarbonyl, (1-6C)-alkoxycarbonyl, (2-6C)-alkenyloxycarbonyl, (2-6C)-alkynoxycarbonyl, aryloxycarbonyl, (1-6C)-alkylsulfinyl or (1-6C)-alkylsulfonyl; and T2>T1> or NO2. When R1> and R2> form 6C carbocycle, then R5> and R4> cannot be 2C-alkyl. An independent claim is also included for the preparation of (I). [Image] ACTIVITY : Plant Growth Regulant; Herbicide. MECHANISM OF ACTION : None given.