Patent EP-2210879-A1 (EP)
Inventor: MINN KLEMENS
IPC: C07D239/48
Filed: 2008-12-30
Abstract: Pyrimidine derivative (I) or its salt is new. Pyrimidine derivative of formula (I) or its salt is new. R 1 and R 2 : 3-8C cycloalkyl (optionally substituted by 1-6C-alkyl or halogen); 6-14C-aryl, 6-14C-aryloxy, 6-14C-arylcarbonyl or 6-14C-aryl-oxycarbonyl (all substituted by halogen, 1-6C-alkyl or 1-6C-haloalkyl); H, halogen, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH 2; 1-6C-alkyl, 1-6C-haloalkyl, 1-6C-alkylcarbonyl, 1-6C-haloalkylcarbonyl, 1-6C-alkylcarbonyloxy, 1-6C-haloalkylcarbonyloxy, 1-6C-alkylcarbonyl-(1-4C)-alkyl; 1-6C-alkoxy, 1-6C-haloalkoxy, 1-6C-alkoxycarbonyl, 1-6C-haloalkoxycarbonyl, 1-6C-alkoxycarbonyl-1-6C-alkyl, 1-6C-halo-alkoxycarbonyl-1-6C-alkyl, 1-6C-alkoxycarbonyl-1-6C-haloalkyl, 1-6C-haloalkoxycarbonyl-1-6C-haloalkyl; (2-6C)-alkenyl, 2-6C-haloalkenyl, 2-6C-alkenylcarbonyl, 2-6C-haloalkenylcarbonyl, 2-6C-alkenyloxy, 2-6C-haloalkenyloxy, 2-6C-alkenyloxycarbonyl, 2-6C-haloalkenyloxycarbonyl; 2-6C-alkynyl, 2-6C-haloalkynyl, 2-6C-alkynylcarbonyl, 2-6C-haloalkynylcarbonyl, 2-6C-alkynyloxy, 2-6C-haloalkynyloxy, 2-6C-alkynyloxycarbonyl, 2-6C-haloalkynyloxycarbonyl; tri-1-6C-alkylsilyl-2-6C-alkynyl, di1-6C-alkylsilyl-2-6C-alkynyl, mono-1-6C-alkylsilyl-2-6C-alkynyl; phenylsilyl-2-6C-alkynyl; 6-14C-aryl-1-6C-alkyl, 6-14C-aryl-1-6C-alkoxy, 6-14C-aryl-1-6C-alkylcarbonyl, 6-14C-aryl-1-6C-alkylcarbonyloxy, 6-14C-aryl-1-6C-alkoxycarbonyl, 6-14C-aryl-1-6C-alkoxycarbonyloxy; mono((1-6C)-alkyl)amino, mono(1-6C-haloalkyl)amino, di(1-6C-alkyl)amino, di(1-6C-haloalkyl)amino, (1-6C-alkyl-1-6C-haloalkyl)amino, N-(1-6C-alkanoyl)amino, N-(1-6C-haloalkanoyl)amino, aminocarbonyl-1-6C-alkyl, di-1-6C-alkylaminocarbonyl-1-6C-alkyl; mono((1-6C)-alkyl)aminocarbonyl, mono(1-6C-haloalkyl)aminocarbonyl, di(1-6C-alkyl)aminocarbonyl, di(1-6C-haloalkyl)aminocarbonyl, (1-6C-alkyl-1-6C-haloalkyl)aminocarbonyl, N-(1-6C-alkanoyl)aminocarbonyl, N-(1-6C-haloalkanoyl)aminocarbonyl, mono(6-14C-aryl)aminocarbonyl, di(6-14C-aryl)aminocarbonyl, 1-6C-alkoxy-(1-6C)-alkyl, 1-6C-alkoxy-1-6C-alkoxy, 1-6C-alkoxycarbonyl-1-6C-alkoxy; 3-8C-cycloalkoxy, 3-8C-cycloalkyl-1-6C-alkyl, 3-8C-cycloalkyl-1-6C-haloalkyl, 3-8C-cycloalkyl-1-6C-alkoxy, 3-8C-cycloalkyl-1-6C-haloalkoxy, 3-8C-cycloalkylcarbonyl, 3-8C-cycloalkoxycarbonyl, 3-8C-cycloalkyl-1-6C-alkylcarbonyl, 3-8C-cycloalkyl-1-6C-haloalkylcarbonyl, 3-8C-cycloalkyl-1-6C-alkoxycarbonyl, 3-8C-cycloalkyl-1-6C-haloalkoxycarbonyl, 3-8C-cycloalkylcarbonyloxy, 3-8C-cycloalkoxycarbonyloxy, 3-8C-cycloalkyl-1-6C-alkylcarbonyloxy, 3-8C-cycloalkyl-1-6C-haloalkylcarbonyloxy, 3-8C-cycloalkyl-1-6C-alkoxycarbonyloxy, 3-8C-cycloalkyl-1-6C-haloalkoxy-carbonyloxy; 3-8C cycloalkenyl, 3-8C-cycloalkenyloxy, 3-8C-cycloalkenyl-1-6C-alkyl, 3-8C-cycloalkenyl-1-6C-haloalkyl, 3-8C-cycloalkenyl-1-6C-alkoxy, 3-8C-cycloalkenyl-1-6C-haloalkoxy, 3-8C-cycloalkenylcarbonyl, 3-8C-cycloalkenyloxycarbonyl, 3-8C-cycloalkenyl-1-6C-alkylcarbonyl, 3-8C-cycloalkenyl-1-6C-haloalkylcarbonyl, 3-8C-cycloalkenyl-1-6C-alkoxycarbonyl, 3-8C-cycloalkenyl-1-6C-haloalkoxycarbonyl, 3-8C-cycloalkenylcarbonyloxy, 3-8C-cycloalkenyloxycarbonyloxy, 3-8C-cycloalkenyl-1-6C-alkylcarbonyloxy, 3-8C-cycloalkenyl-1-6C-haloalkylcarbonyloxy, 3-8C-cycloalkenyl-1-6C-alkoxycarbonyloxy, 3-8C-cycloalkenyl-1-6C-haloalkoxycarbonyloxy; hydroxy-1-6C-alkyl, hydroxy-1-6C-alkoxy, cyano-1-6C-alkoxy, cyano-1-6C-alkyl; 1-6C-alkylsulfonyl, 1-6C-alkylthio, 1-6C-alkylsulfinyl, 1-6C-haloalkylsulfonyl, 1-6C-haloalkylthio, 1-6C-haloalkylsulfinyl, 1-6C-alkylsulfonyl-1-6C-alkyl, 1-6C-alkylthio-1-6C-alkyl, 1-6C-alkylsulfinyl-1-6C-alkyl, 1-6C-haloalkylsulfonyl-1-6C-alkyl, 1-6C-haloalkylthio-1-6C-alkyl, 1-6C-haloalkylsulfinyl-1-6C-alkyl, 1-6C-alkylsulfonyl-1-6C-haloalkyl, 1-6C-alkylthio-1-6C-haloalkyl, 1-6C-alkylsulfinyl-1-6C-haloalkyl, 1-6C-haloalkylsulfonyl-1-6C-haloalkyl, 1-6C-haloalkylthio-1-6C-haloalkyl, 1-6C-haloalkylsulfinyl-1-6C-haloalkyl, 1-6C-alkylsulfonyloxy, 1-6C-haloalkylsulfonyloxy, 1-6C-alkylthiocarbonyl, 1-6C-haloalkylthiocarbonyl, 1-6C-alkylthiocarbonyloxy, 1-6C-haloalkylthiocarbonyloxy, 1-6C-alkylthio-1-6C-alkyl, 1-6C-alkylthio-1-6C-alkoxy, 1-6C-alkylthio-1-6C-alkylcarbonyl, 1-6C-alkylthio-1-6C-alkylcarbonyloxy, 4-14C arylsulfonyl, 6-14C-arylthio, 6-14C-arylsulfinyl, 3-8C-cycloalkylthio, 3-8C-alkenylthio, 3-8C-cycloalkenylthio, or 3-6C alkynylthio; R 1+R 2 : 2-6C-alkylene group, which comprises oxygen or sulfur atoms (mono- or poly-substituted by halogen); R 3 : H, 1-6C-alkyl or 1-6C-haloalkyl; R 4 and R 5 : H, 1-6C-alkyl, 1-6C-haloalkyl, hydroxy, 1-6C-alkoxy or 1-6C-haloalkoxy;or R 4+R 5+C : three- to seven-membered ring; R 6 and R 7 : H, 1-6C-alkyl, 1-6C-haloalkyl, 1-6C-alkoxy, 1-6C-haloalkoxy, 6-14C-aryl, 6-14C-aryloxy, 6-14C-arylcarbonyl or 6-14C-aryloxycarbonyl; R 6+R 7 : 2-7C-alkylene group comprise oxygen and/or sulfur atoms (mono- or poly-substituted by halogen); R 8, R 9, R 1 0 and R 1 1 : H, halogen, cyano, 1-6C-alkyl, 1-6C-alkylcarbonyl, 1-6C-alkyloxycarbonyl, 1-6C-alkylaminocarbonyl, 1-6C-dialkylaminocarbonyl, 1-6C-haloalkyl, 1-6C-alkoxy, 1-6C-haloalkoxy, 2-6C-alkynyl, 2-6C-haloalkynyl, 2-6C-alkynylcarbonyl, 2-6C-haloalkynylcarbonyl, 2-6C-alkynyloxy, 2-6C-haloalkynyloxy, 2-6C-alkynyloxycarbonyl, 2-6C-haloalkynyloxycarbonyl or nitro; X : bond, CH 2, O, S, carbonyl, NH, CR 1 2R 1 3 or NR 1 4; R 1 2 and R 1 3 : H, 1-6C-alkyl or 1-6C-haloalkyl;and R 1 4 : H, 1-6C-alkyl, or 1-6C-haloalkyl. An independent claim is included for preparation of compound (I). [Image] ACTIVITY : Herbicide; Plant growth regulant. The pre-emergence herbicidal efficacy of 4-amino-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidine-5-carbonitrile (Ia) against Alopecurus myosuroides was tested as follows: compound (Ia) was applied at the rate of 320 l/hectare and percentage control of weed was measured. The compound (Ia) showed 100% control of weed. MECHANISM OF ACTION : None given.