New benzyl, benzoyl or anilino-substituted triazinedionethiones, useful as pre- or post-emergence, total or selective herbicides

    公开(公告)号:DE19924805A1

    公开(公告)日:2000-11-30

    申请号:DE19924805

    申请日:1999-05-29

    Applicant: BASF AG

    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).

    1-ARYL-1,3,5-TRIAZINE-4-THIONE-2,6-DIONES, PRODUCTION THEREOF AND USE THEREOF AS HERBICIDES

    公开(公告)号:CA2364660A1

    公开(公告)日:2000-08-31

    申请号:CA2364660

    申请日:2000-02-10

    Applicant: BASF AG

    Abstract: The invention relates to novel 1-aryl-4-thiotriazines of formula (I), wherei n R1 = H, NH2, C1-C4-alkyl, C1-C4-alkyl halide; R2 = H, NH2, C1-C4-alkyl, C1-C 4- alkyl halide; R3 = H, halogen; R4 = CN, halogen; Y = nitrogen, the methine group or together with R5, a bridge ~C-O-C(R6)=N-; R5 = 1) hydrogen, hydroxy , mercapto, nitro, halogen, C1-C6-alkyl, C1-C6-alkyl halide, 2) C1-C6-alkoxy, C1- C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2- C6- alkenylthio, C2-C6-alkinyloxy or C2-C6-alkinylthio, each of these 8 radicals optionally bearing one of the following substituents: halogen, cyano, -CO-R8 , - CO-OR8 or -CO-N(R8)-R9; 3) -CO-R11, -C(R11)(OR13)(OR14), -C(R11)=C(R15)-CO- R16, -CH(R11)-CH(R15)-CO-R16, -CO-OR20, -C(R10)=N-OR7, -N(R21)-R22 or -CO- N(R21)-R22; and R6 = H, halogen, optionally substituted C1-C6-alkyl, C3-C6- alkenyl, C3-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3 - C6-cycloalkyl or C3-C6-cycloalkoxy. The invention also relates to salts and enol ethers of the inventive compounds (I), to a method for producing them a nd to their use as herbicides.

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