Patent DE-19924805-A1 (DE)
Title: New benzyl, benzoyl or anilino-substituted triazinedionethiones, useful as pre- or post-emergence, total or selective herbicides
Inventor: MENKE OLAF
IPC: C07D251/38
Filed: 1999-05-29
Abstract: 5-Benzyl-, 5-benzoyl- or 5-anilino-triazinedionethiones (I) are new. Triazinedionethiones of formula (I) and their salts and enol ethers are new.  X  = CH2, C(O) or NH;  R1, R2  = Me or NH2;  R3  = H, CN, SCN, halo, T', OT' or ST';  T'  = 1-4C haloalkyl;  R4  = as R4; T, alkenyloxy or alkynyloxy; alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkylaminocarbonyl, hydroxyalkylcarbonyl, NHSO2T or NH2 (all optionally substituted (os) by OT, COOT, NH2 or NHSO2T); T  = 1-4C alkyl;  one of R5, R6  = H, CN, NO2, halo or OT;  the other R5, R6  = H, CN, NO2, halo or NH2; alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, alkenyloxy, 5-7C cycloalkenyloxy, alkenylthio, alkynylthio, alkylcarbonyloxy, alkylcarbonylthio, alkoxycarbonyloxy, alkenylcarbonyloxy, alkenylcarbonylthio, alkynylcarbonyloxy, alkynylcarbonylthio, alkylsulfonyl or alkylsulfonyloxy (all os by 1-4 R'6);-C(Y)-R14, -C(R14)(Z1R15)(Z2R16), C(R14)=C(R17)-CN, C(R14)=C(R17)-COR18, CHR14CHR17-COR18, C(R14)=C(R17)CH2COR18, C(R14)=C(R17)-C(R19)=C(R20)-COR18, C(R14)=C(R17)-CH2CHR21-COR18, COOR22, -CC-CONHOR9, -CC-CON(R22)OR9, -CC-CSNHOR9, -CC-CSN(R22)OR9, -CC-C(R10)=NOR9, -C(R14)=C(R17)-CONHOR9, C(R14)=C(R17)-CON(R22)OR9, C(R14)=C(R17)-CSNHOR9, C(R14)=C(R17)-CSN(R22)OR9, C(R14)=C(R17)-C(R10)=NOR9, NR24R25, -CC-Q or C(R14)=C(R17)-Q; or (iv) CON(R22)OR9, -C(R10)=NOR9, -C(Z1R15)(Z2R16)OR23, -C(Z1R15)(Z2R16)SR23, -C(Z1R15)(Z2R16)NR24R25, Q, COOR23, COSR23, alkylthioalkylcarbonyl or alkyliminooxycarbonyl;  R'6  = halo, NO2, CN, OH, cycloalkyl, alkoxy, cycloalkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, 1-6C alkylideneaminooxy, Ph', OPh', SO2Ph', Het, -O-Het, =O, COR7, COOR7, COSR7, CONR7R8, OCOCR7, OCOOR7, OCOSR7, OCOCNR7R8, NR7R8, =NOR9, -C(R10)=NOR9 or SiR11R12R13;  Ph'  = phenyl (os by 1-3 of halo, NO2, CN, alkyl, haloalkyl, alkoxy and alkoxycarbonyl);  Het  = 3-7 heterocyclyl (os by 1-3 of halo, NO2, CN, alkyl, haloalkyl, alkoxy and alkylcarbonyl);  Z1, Z2  = O or S;  Q  = (a);  Q1  = 1-3C alkylene (os by alkyl);  Q2  = O or S;  R7  = H, alkyl, cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, alkoxyalkyl, alkoxycarbonylalkyl, (3-6C) alkenyloxycarbonylalkyl, Ph' or Ph'-alkyl;  R8  = H, OH, alkyl, cycloalkyl, alkoxy, alkoxycarbonylalkoxy, 3-6C alkenyl or 3-6C alkenyloxy;  NR7R8  = Het;  R9  = H, alkyl, haloalkyl, cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, alkylcarbonylakyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkylcarbonyloxyalkyl or Ph'-alkyl;  R10  = H or halo; alkyl, haloalkyl, alkoxy, haloalkoxy, 3-6C alkenyloxy, alkylthio, haloalkylthio, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylsulfonyloxy or haloalkylsulfonyloxy (all os by OH, CN, COOH, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, mono- or dialkylaminocarbonyl or alkylcarbonyloxy); 3-7 azaheterocycle, bonded at N via a carbonyl bridge; alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxycarbonyloxy, alkylcarbonylthio, haloalkylcarbonylthio, alkoxycarbonylthio, alkenyl, alkenylthio, 3-6C alkynyl, 3-6C alkynyloxy, 3-6C alkynylthio, alynylcarbonyloxy, 3-6C alkynylsulfonyloxy, cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylcarbonyloxy or cycloalkylsulfonyloxy; or Ph', Ph'O, Ph'S, Ph'COO, Ph'SO2O, Ph'-alkyl, Ph'-alkoxy, Ph'-alkylthio, or Ph'-alkylsulfonyloxy;  R14  = H, CN, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl or alkoxycarbonyl;  R15, R16  = alkyl, haloalkyl, 3-6C alkenyl, 3-6C alkynyl or alkoxyalkyl;  R15 + R16  = 2-4 (un)saturated C, substituted by 1-3 of CN, NO2, halo, alkyl, alkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, 3-6C alkenyloxyalkyl, (3-6C) alkynyloxyalkyl, cycloalkyl, cycloalkoxy, COOH, alkoxycarbonyl, alkylcarbonyloxy or Ph' and/or having 1 or 2 members forming part of a 3-7 ring, and os by 1 or 2 of CN, alkyl, alkenyl, alkoxy, cyanoalkkyl, haloalkyl and alkoxycarbonyl;  R17  = H, CN, halo, alkyl, haloalkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl;  R18  = H, OR23 SR23, alkyl (os by 1 or 2 alkoxy), alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylthioalkyl, alkyliminooxy, NR24R25 or Ph';  Ph''  = phenyl (os by 1-3 of CN, NO2, halo, alkyl, 3-6C alkenyl, haloalkyl, alkoxy and alkoxycarbonyl);  R19  = H, CN, halo, alkyl, 3-6C alkenyl, 3-6C alkynyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, NR24R25 or Ph'';  R20  = H, CN, halo, alkyl, alkoxy, haloalkyl, alkylcarbonyl or alkoxycarbonyl;  R21  = H, CN, alkyl or alkoxycarbonyl;  R22, R23  = H; alkyl, haloalkyl, alkenyl or alkynyl (all os by 1 or 2 of CN, halo, OH, COOH, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, (3-6C) alkenyloxycarbonyl or 3-7 azaheterocycle (optionally containing O or S), bonded at N via a carbonyl bridge); or alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, mono- or dialkylaminoalkyl, alkoxyiminoalkyl, cycloalkyl, Ph' or Ph'-alkyl; R24, R25  = H, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl (os in the alkenyl part by 1-3 halo and CN), alkylsulfonyl, alkoxycarbonylalkylsulfonyl, Ph'', Ph''SO2, Ph''CH2 or Ph''CH2SO2;  NR24R25  = (un)saturated 4-7  ring, optionally containing a further O, S, N, NH or N(alkyl);  Y  = O, S or N(R28); R28  = H, OH, alkyl, 3-6C alkenyl, 3-6C alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, cycloalkoxy, 5-7C cycloalkenyloxy, haloalkoxy, 3-6C haloalkenyloxy, hydroxyalkoxy, cyanoalkyl, cycloalkylalkoxy, alkoxyalkoxy, alkoxy-(3-6C) alkenyloxy, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylcarbonylalkyl, alkylcarbonylalkoxy, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, alkylthioalkoxy, dialkylaminoalkoxy or Ph''; Ph''-alkoxy, Ph''-(3-6C) alkenyloxy or Ph''-(3-6C) alkynyloxy ( 1 or 2 CH2 in the C chains may be replaced by O, S or N(alkyl)); Het, Het-alkoxy, Het-(3-6C) alkenyloxy or Het-(3-6C) alkynyloxy (1 or 2 CH2 in the C chains may be replaced by O, S or N(alkyl)); or NR29R30; R29, R30  = H, alkyl, 3-6C alkenyl, 3-6C alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl (os in the alkenyl part by 1-3 of halo and CN) or Ph''; and NR29R30  = (un)saturated 4-7 ring, optionally containing a further O, S, N, NH or N(alkyl).  An Independent claim is included for the preparation of (I).