Patent EP-2589598-A1 (EP)
IPC: A01N43/653
Filed: 2011-11-03
Abstract: Substituted heteroaryl carboxylic acid amide compounds (I) are new. Substituted heteroaryl carboxylic acid amide compounds of formula (I) or their salts are new. A : N or CY1; B1 : N or CH; X : 1-6C alkyl-heterocyclyl (substituted by n number of oxo) or 1-6C alkyl-heteroaryl (both substituted by s number of 1-6C alkyl or 1-6C alkoxy (both optionally halogenated), halo or S(O) n-1-6C alkyl) or 1-6C alkyl, 2-6C alkenyl, 3-6C cycloalkyl or 3-6C cycloalkyl-1-6C alkyl (all optionally halogenated), NO 2, halo, CN, formyl, thiocyanato, 2-6C alkynyl, halo-3-6C alkynyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1) 2, NR1C(O)N(R1) 2, OC(O)N(R1) 2, C(O)NR1OR1, OR1, OCOR1, OSO 2R2, S(O) nR2, SO 2OR1, SO 2N(R1) 2, NR1SO 2R2, NR1COR1, 1-6C alkyl-S(O) nR2, 1-6C alkyl-OR1, 1-6C alkyl-OCOR1, 1-6C alkyl-OSO 2R2, 1-6C alkyl-CO 2R1, 1-6C alkyl-SO 2OR1, 1-6C alkyl-CON(R1) 2, 1-6C alkyl-SO 2N(R1) 2, 1-6C alkyl-NR1COR1, 1-6C alkyl-NR1SO 2R2, NR1R2, P(O)(OR5) 2or CH 2P(O)(OR5) 2; Y1 : 1-6C alkyl-heterocyclyl or heterocyclyl (both substituted by n number of oxo), 1-6C alkyl-phenyl, 1-6C alkyl-heteroaryl, phenyl or heteroaryl (all substituted by s number of 1-6C alkyl or 1-6C alkoxy (both optionally halogenated), halo, NO 2, CN, 3-6C cycloalkyl, S(O) n-1-6C alkyl, 1-6C alkoxy-1-4C alkyl or cyanomethyl) or 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl or 3-6C cycloalkyl-1-6C alkyl (all optionally halogenated), H, NO 2, halo, CN, thiocyanato, 3-6C cycloalkenyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1) 2, NR1C(O)N(R1) 2, OC(O)N(R1) 2, CO(NOR1)R1, NR1SO 2R2, NR1COR1, OR1, OSO 2R2, S(O) nR2, SO 2OR1, SO 2N(R1) 2, 1-6C alkyl-S(O) nR2, 1-6C alkyl-OR1, 1-6C alkyl-OCOR1, 1-6C alkyl-OSO 2R2, 1-6C alkyl-CO 2R1, 1-6C alkyl-CN, 1-6C alkyl-SO 2OR1, 1-6C alkyl-CON(R1) 2, 1-6C alkyl-SO 2N(R1) 2, 1-6C alkyl-NR1COR1, 1-6C alkyl-NR1SO 2R2, N(R1) 2, P(O)(OR5) 2or CH 2P(O)(OR5) 2; Z : heteroaryl, heterocyclyl (substituted by n number of oxo) or phenyl (all substituted by s number of 1-6C alkyl or 1-6C alkoxy (both optionally halogenated), halo, NO 2, CN, 3-6C cycloalkyl or S(O) n-1-6C alkyl) or 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl or 3-6C cycloalkyl-1-6C alkyl (all optionally halogenated), halo, CN, thiocyanato, halo-1-6C alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1) 2, NR1C(O)N(R1) 2, OC(O)N(R1) 2, C(O)NR1OR1, OSO 2R2, S(O) nR2, SO 2OR1, SO 2N(R1) 2, NR1SO 2R2, NR1COR1, 1-6C alkyl-S(O) nR2, 1-6C alkyl-OR1, 1-6C alkyl-OCOR1, 1-6C alkyl-OSO 2R2, 1-6C alkyl-CO 2R1, 1-6C alkyl-SO 2OR1, 1-6C alkyl-CON(R1) 2, 1-6C alkyl-SO 2N(R1) 2, 1-6C alkyl-NR1COR1, 1-6C alkyl-NR1SO 2R2, N(R1) 2or P(O)(OR5) 2, or H, 1-6C alkyl or 1-6C alkoxy (if Y = S(O) nR2); W1 : 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl (all optionally halogenated), 3-7C (halo)cycloalkyl, 1-6C (halo)alkoxy, S(O) n-1-6C (halo)alkyl, 1-6C alkoxy-1-4C (halo)alkyl, halo, NO 2, NR3COR3 or CN; R : 1-8C alkyl, 2-8C alkenyl or 2-8C alkynyl (all optionally halogenated and all substituted by s number of heterocyclyl or Q-heterocyclyl (both substituted by n number of oxo), heteroaryl, phenyl, Q-heteroaryl, Q-phenyl or Q-benzyl (all substituted by s number of CH 3, ethyl, OCH 3, CF 3, CN or halo), OH, NO 2, CN, Si(R5) 3, PO(OR5) 2, S(O) n-1-6C (halo)alkyl, 1-6C alkoxy (optionally halogenated), N(R3) 2, COR3, COOR3, OCOR3, NR3COR3, NR3SO 2R4, O-1-2C alkyl-3-6C cycloalkyl or 3-6C cycloalkyl) or 3-7C cycloalkyl, heteroaryl, heterocyclyl (substituted by n number of oxo) or phenyl (all substituted by s number of 1-6C alkyl or 1-6C alkoxy (both optionally halogenated), halo, NO 2, CN, 3-6C cycloalkyl, S(O) n-1-6C alkyl or 1-6C alkoxy-1-4C alkyl); Q : O, S or NR3; R1 : heterocyclyl, 1-6C alkyl-heterocyclyl, 1-6C alkyl-O-heterocyclyl or 1-6C alkyl-NR3-heterocyclyl (all substituted by n number of oxo), 1-6C (halo)alkyl, 2-6C (halo)alkenyl, 2-6C (halo)alkynyl, 3-6C cycloalkenyl, 3-6C (halo)cycloalkyl, 1-6C alkyl-O-1-6C alkyl, 3-6C cycloalkyl-1-6C alkyl, phenyl, phenyl-1-6C alkyl, heteroaryl, 1-6C alkyl-heteroaryl, 1-6C alkyl-O-heteroaryl or 1-6C alkyl-NR3-heteroaryl (all substituted by s number of CN, halo, NO 2, thiocyanato, OR3, S(O) nR4, N(R3) 2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO 2R4, CO 2R3, COSR4, CON(R3) 2or 1-4C alkoxy-2-6C alkoxycarbonyl); R2 : heterocyclyl, 1-6C alkyl-heterocyclyl, 1-6C alkyl-O-heterocyclyl or 1-6C alkyl-NR3-heterocyclyl (all substituted by n number of oxo), 1-6C (halo)alkyl, 2-6C (halo)alkenyl, 2-6C (halo)alkynyl, 3-6C cycloalkenyl, 3-6C (halo)cycloalkyl, 1-6C alkyl-O-1-6C alkyl, 3-6C cycloalkyl-1-6C alkyl, phenyl, phenyl-1-6C alkyl, heteroaryl, 1-6C alkyl-heteroaryl, 1-6C alkyl-O-heteroaryl or 1-6C alkyl-NR3-heteroaryl (all substituted by s number of CN, halo, NO 2, thiocyanato, OR3, S(O) nR4, N(R3) 2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO 2R4, CO 2R3, COSR4, CON(R3) 2or 1-4C alkoxy-2-6C alkoxycarbonyl); R3 : H, 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl, 3-6C cycloalkyl-1-6C alkyl or phenyl; R4 : 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl, 3-6C cycloalkyl-1-6C alkyl or phenyl; R5 : 1-4C alkyl; n : 0-2; and s : 0-3. An independent claim is also included for an herbicidal agent comprising (I). [Image] ACTIVITY : Herbicide. The herbicidal activity of (I) was tested against Alopecurus myosuroides. The results showed that 2-chloro-5-methyl-3-methylthio-N-(1-methyltetrazole-5-yl)-benzamide exhibited 80% herbicidal effect when compared with untreated plants, which exhibited 0% herbicidal effect. MECHANISM OF ACTION : None given.