Patent DE-19738084-A1 (DE)
Title: New 3-aryl-methyl-uracil derivatives
Inventor: MENKE OLAF DR
IPC: C07D413/06
Filed: 1997-09-01
Abstract: 3-Arylmethyluracil derivatives (I.1)-(I.4) are new, where A  =  H, 1-4C alkyl, NH2, 1-4C alkylamino or di-(1-4C alkyl)amino; X  =  O or S; n = not defined; R1  =  1-4C haloalkyl; R2  =  H, halo or 1-3C alkyl; R3-R5 = H, CN, thiocyanato, halo, 1-4C haloalkyl, 1-4C haloalkoxy, 1-4C haloalkylthio, 1-4C alkyl or 1-4C alkoxy; R6, R7 = 1-4C alkyl, NH2, 1-4C alkylamino or di(1-4C alkyl)amino, or R6 and R7 together form =O; R8 may be in position  alpha  or  beta  and R3 is in the other position; R8  =  (1) H, halo, amino, 1-4C alkylsulphonylamino or di(1-4C alkyl)amino; (2) 1-6C alkoxy, 1-6C alkylthio, 3-6C cycloalkoxy, 3-6C cycloalkylthio, 2-6C alkenyloxy, 5-7C cycloalkenyloxy, 2-6C alkenylthio, 2-6C alkynyloxy, 2-6C alkynylthio, (1-6C alkyl)carbonyloxy, (1-6C alkyl)carbonylthio, (1-6C alkoxy)carbonyloxy, (2-6C alkenyl)carbonyloxy, (2-6C alkenyl)carbonylthio, (2-6C alkynyl)carbonyloxy, (2-6C alkynyl)carbonylthio, 1-6C alkylsulphonyloxy or 1-6C alkylsulphonyl, where the last 18 groups may contain 1-4 substituents; (3) CT-R11, C(R11)(Y1R12)(Y2R13), C(R11)=C(R14)CN, C(R11)=C(R14)CO-R15, CH(R11)-CH(R14)CO-R15, C(R11)=C(R14)-CH2-CO-R15, C(R11)=C(R14)-C(R16)=C(R17)-CO-R15, C(R11)=C(R14)-CH2-CH(R18)CO-R15, CO-OR19, CO-SR19, CO-N(R19)-OR20, C?=C-CO-NH-OR20, C?=C-CO-N(R19)-OR20, , C?=C-CS-NH-OR20, C?=C-CS-N(R19)-OR20, C(R11)=C(R14)-CO-NH-OR20, C(R11)=C(R14)-CO-N(R19)-OR20, C(R11)=C(R14)-CS-NH-OR20, C(R11)=C(R14)-CS-N(R19)-OR20, C(R11)=C(R14)-C(R21)=N-OR20, C(R21)=N-OR20, C?=C-C(R21)=N-OR20, C(Y1R12)(Y2R13)-OR19, C(Y1R12)(Y2R13)-SR19, C(Y1R12)(Y2R13)-N(R23)(R24), N(R23)(R24), CO-N(R23)(R24), or groups of formula (i), (ii), -C?=C-(i), -C?=C-(ii), -C(R11)=C(R14)-(i) or -C(R11)=C(R14 )-(ii); Y1, Y2 = S or O;  theta  = 1-3C alkylene optionally substituted by 1-6C alkyl; R11  =  H, CN, 1-6C alkyl, 1-6C haloalkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl, 1-6C alkoxy-(1-6C alkyl) or (1-6C alkoxy)carbonyl; R12, R13 = 1-6C alkyl, 1-6C haloalkyl, 3-6C alkenyl, 3-6C alkynyl or 1-6C alkoxy-(1-6C alkyl) or R12 and R13 together form a 2-4 membered carbon chain which is optionally substituted and can contain non-adjacent O, S or N atoms instead of C atoms or be condensed or form a spiro attachment with a 3-7 membered ring; R14 =  H, CN, halo, 1-6C alkyl, 1-6C haloalkyl, 1-6C alkoxy, (1-6C alkyl)carbonyl or (1-6C alkoxy)carbonyl; R15 = H, OR22, SR22, 1-6C alkyl (optionally substituted by one or two 1-6C alkoxy groups), 2-6C alkenyl, 2-6C alkynyl, 1-6C haloalkyl, 3-6C cycloalkyl, 1-6C alkylthio-(1-6C alkyl), 1-6C alkyliminooxy, N(R23)(R24) or optionally substituted phenyl; R22 has the same meanings as R19; R16 = H, CN, halo, 1-6C alkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkoxy-(1-6C alkyl), (1-6C alkyl)carbonyl, (1-6C alkoxy)carbonyl, N(R25)(R26) or optionally substituted phenyl; R25, R26 have the same meanings as R23 and R24; R17 = H, halo, CN, 1-6C alkyl, 1-6C alkoxy, 1-6C haloalkyl, (1-6C alkyl)carbonyl or (1-6C alkoxy)carbonyl; R18 = H, CN, 1-6C alkyl or (1-6C alkoxy)carbonyl; R19 = H, 1-6C alkyl, 1-6C haloalkyl, 2-6C alkenyl or 2-6C alkynyl (where the latter four groups are optionally substituted), (1-6C alkyl)carbonyl, (1-6C haloalkyl)carbonyl, (1-6C alkoxy)carbonyl, 1-6C alkylaminocarbonyl, di-(1-6C alkyl)aminocarbonyl, 1-6C alkoxyimino-(1-6C alkyl), 3-6C cycloalkyl, phenyl or phenyl-(1-6C alkyl), where the phenyl ring is optionally substituted; R20 = H, 1-6C alkyl, 1-6C haloalkyl, 3-6C cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, hydroxy-(1-6C alkyl), 1-6C alkoxy-(1-6C alkyl), 1-6C alkylthio-(1-6C alkyl), cyano-(1-6C alkyl), (1-6C alkyl)carbonyl-(1-6C alkyl), (1-6C alkoxy)carbonyl-(1-6C alkyl), (1-6C alkoxy)carbonyl-(2-6C alkenyl), (1-6C alkyl)carbonyloxy-(1-6C alkyl) or phenyl-(1-6C alkyl), where the phenyl ring may contain 1-3 substituents; R