Patent DE-10021568-A1 (DE)
Title: New pyrimidinyl aryl sulfoxide or sulfone derivatives useful as herbicides and plant growth inhibitors
Inventor: LUETHY CHRISTOPH
IPC: C07D239/60
Filed: 2000-05-03
Abstract: Pyrimidinyl aryl sulfoxide or sulfone derivatives (I) are new. Pyrimidinyl aryl sulfoxide or sulfone derivatives of formula (I) and their isomers and salts are new. R1, R2  = H, halo, R, 1-8C haloalkyl, CH2OA, 3-8C cycloalkyl, 2-8C alkenyl, 2-8C alkynyl, OH, OR, 1-8C haloalkoxy, OA'OA, SR, 1-8C haloalkylthio, OAr, SAr, NH2, NHA or NAA;  R  = 1-8C alkyl;  A  = 1-4C alkyl;  A'  = 1-4C alkylene; Ar  = phenyl optionally substituted by halo, A, 1-4C haloalkyl, OA, 1-4C haloalkoxy, NO2 and CN;  R3  = a group of formula (i) or (ii); Y = O, S or NR12;  R4  = H, halo, CN, R, 2-8C alkenyl, 3-8C cycloalkyl, 1-8C haloalkyl, OR, (1-8C)alkoxy(1-8C)alkyl, CH2OH, CHO, COOH, COOR, or phenyl or benzyl optionally substituted by halo, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2;  R5  = H, R, halo or OH, 1-8C alkoxy (optionally substituted by halogen, 2-8C alkenyl, 2-8C haloalkenyl, 2-8C alkynyl, 2-8C haloalkynyl, 3-8C cycloalkyl, OH, OR, SR, SOR, SO2R, CN, COOR, CONH2, CONHR, CONRR, 3-8C alkylideneaminooxy or optionally substituted phenyl), 3-8C cycloalkoxy, formyloxy, COOR, 2-8C alkenylcarbonyloxy, 3-8C cycloalkylcarbonyloxy, benzoyloxy (optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2), OCOOR, OCONRR, SR, SOR, SO2R, CONH2, CN, or phenoxy or phenylthio (both optionally substituted by halo, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2);  X  = O, CHOH, CHOR15, C(OR15)2, C=NR8 or CR18R19;  R6  = H, OH, SH, 1-8C alkoxy or 1-8C alkylthio (both optionally substituted by halo, NO2, CN, OR, SR, SOR, SO2R, Ar', OAr', SAr', SOAr'. SO2Ar', OCH2Ar' SCH2Ar' or COAr', OCOOR or dialkylamino), benzyloxy (optionally substituted by halogen, A, 1-4C haloalkyl, OA or 1-4C haloalkoxy), 3-8C alkenyloxy, 3-8C haloalkenyloxy; 3-8C alkynyloxy, OA'COA, OA'OCOA, OA'SiA3, (1-8C alkylideneaminooxy)ethoxy, OAr, SAr; NR10R11, imidazolyl or -O-N=C(R20)(R21); Ar'  = phenyl (optionally substituted by halogen, R, 1-4C haloalkyl, NH2, NHR, NAA and 1-4C haloalkoxy);  R7  = H, halo, OR, 1-8C alkyl (optionally substituted by halo, OR, SR, SOR, SO2R, COA or CN), 2-8C alkenyl (optionally substituted by halogen, OA or NAA) Ar or CH2Ar;  R8  = H, OH, R, 3-8C cycloalkyl, 1-8C haloalkyl, 1-8C alkoxy (optionally substituted by halo, OA, alkoxycarbonyl, 3-8C cycloalkyl, acyl, NRR or benzyloxy (optionally substituted by halogen, R or OR)), (1-8C)alkoxy(1-8C)alkyl, 2-8C alkenyl, 2-8C alkynyl, 3-8C cycloalkoxy, phenyl or phenoxy (both optionally substituted by halo, A, 3-8C cycloalkyl, 1-4C haloalkyl, OA, 1-4C haloalkoxy, CN or NO2), 3-8C alkenyloxy or alkynyloxy (both optionally substituted by halo or phenyl), benzyloxy (optionally substituted by halo, R, 1-8C haloalkyl, OR or 1-8C haloalkoxy), tetrahydropyranyloxy, OSiA3, OCOR9 or NR16R17;  R9  = R, 3-8C cycloalkyl, 1-8C haloalkyl, OR, Ar, OAr, NH2, NHR or NRR;  R10  = H, 1-8C alkyl (optionally substituted by OH, OA, COOH, COOA, CONH2 or phenyl), 3-8C alkenyl, 3-8C alkynyl, 3-8C cycloalkyl, 1-8C haloalkyl, OR, NHR, NRR, NHAr, N(A)Ar, CH2Ar or Ar;  R11  = H or R;  R12  = H, 1-8C alkyl (optionally substituted by OH, OA, COOH, COOA, CONH2 or phenyl) 3-8C alkenyl, 3-8C alkynyl, 3-8C cycloalkyl, phenyl, OH, OR, 3-8C alkenyloxy, benzyloxy, NHR, NRR, NHAr or N(A)Ar;  R13  = H, halo, CN, CHO, A or 1-4C haloalkyl;  R14  = H, halo, R, 1-8C haloalkyl, 3-8C cycloalkyl, 2-8C alkenyl, 2-8C alkynyl, OH, OR or 1-8C haloalkoxy;  R15  = A; or R15 + R15 = optionally A-substituted OCH2CH2O or OCH2CH2CH2O; R16  = H, R, 3-8C alkenyl, Ar, COAr, COA, COOA, CONHA or CONHAr;  Ar  = phenyl optionally substituted by halo, alkyl, haloalkyl, alkoxy, haloalkoxy, CN or NO2;  R17  = H or R;  R18 = H, halo, 1-8C alkyl (optionally substituted by phenyl, COOA or CN) or Ar;  R19  = H, halo or R;  R20  = H, R, CN, COOA or Ar; R21  = R or Ar;  n  = 1 or 2; or R5 + R4 = optionally A-substituted OCH2CH2CH2; R6 + R7 = NH, NOA, 3-4C alkenyloxyimino, benzyloxyimino, NA, optionally substituted phenylimino, O or S; R6 + R8 = O, NH, NA, NOA or optionally substituted phenylimino; R7 + R8 = forms a 5- or 6-membered ring that can contain another O, S or N atom and is optionally substituted by halogen, A, 1-4C haloalkyl, OA, 1-4C haloalkoxy, SA or 1-4C haloalkylthio; R2 + R13 = CH2CH2O optionally substituted by halo or Me. Independent claims are also included for: (1) the preparation of (I) by oxidizing the corresponding pyrimidinyl aryl sulfides (II); and (2) a herbicidal and plant growth inhibiting composition comprising a compound (I) or (II) on an inert carrier.