New 4-(pyridine-3-carbonyl)-cyclohex-4-ene-1,3-dione derivatives, useful as herbicides and plant growth inhibitors, especially for selective weed control in crops such as cereals, cotton or soya

摘要

5-(Substituted thio, sulfinyl or sulfonyl)-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-cyclohex-4-ene-1,3-dione derivatives (I) are new. Pyridine derivatives of formula (I) (including all stereoisomeric and tautomeric forms) and their salts are new. R = 1-12C alkyl, 2-12C alkenyl, 2-12C alkynyl, 3-12C allenyl, 3-12C cycloalkyl, 5-12C cycloalkenyl, -R'-R1, phenyl (optionally substituted (os) by 1-5 R2), Cyc, halo, 1-12C alkylthio, CN, C(X1)R6, C(X2)X3R7 or C(X4)NR8R9, H, CN, NC, OH or NR8R92; Cyc = 3-12 membered, mono or bicyclic, aromatic, partially saturated or completely saturated ring system, bonded directly (via N or C) or via 1-6C alkylene or 2-6C alkenylene (both optionally interrupted by O or S(O)p), and optionally (i) containing 1-5 N, O or S heteroatoms, (ii) containing 1 or 2 CO groups and/or (iii) substituted by 1-3 R3; R' = 1-12C alkylene or 2-12C alkenylene (both optionally interrupted by O, S(O)p or CO and os by 1-5 R2); R1 = halo, CN, SCN, NO2, OH, OT, 2-6C alkenyloxy, 2-6C alkynyloxy, SH, ST, SOT, SO2T, 2-6C alkenylthio, 2-6C alkenylsulfinyl, 2-6C alkynylthio, 2-6C alkynylsulfinyl, SO3H, OSO2T, OSO2Ph', OCOT, OCOPh', OCOOU, OCOSU, OCSOU, SCSOU, NH2, NHU, NU2, CHO, COT, COOH, COOU, COPh', CSU, CSOU, CONH2, CONHU, Si(OH)3, SiU3, SiPh;Me2, 3-6C cycloalkyl, Ph', OPh', SPh', SOPh' or SO2Ph'; Ph' = phenyl (os by V, OV, halo, CN or NO2); R2, R4 = OH, halo, T, OT, ST, SOT, SO2T, CN, CONH2, COOH, COOU or Ph'; R3 = T', 2-6C alkenyl, 2-6C haloalkenyl, 2-6C alkynyl, 2-6C haloalkynyl, OT', 3-6C alkenyloxy, 3-6C alkynyloxy, SH, ST', 3-6C alkenylthio, 2-6C haloalkenylthio, 3-6C alkynylthio, 3-6C haloalkynylthio, SOT', SO2T', SO2NH2, SO2NHT, SO2NU2, NH2, SNHT, NU2, halo, CN, -R''-R5, Ph' or OPh'; R'' = 1-3C alkylene or 2-3C alkenylene (both optionally interrupted by O or S(O)p and os by R4); R5 = T, (1-3C) alkoxy-(1-3C) alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, COOU, ST, SOT, SO2T, 3-6C alkenylthio, 3-6C alkynylthio or Ph'; R6 = 1-12C alkyl, 3-6C cycloalkyl or Ph'; R7 = 1-12C alkyl; R8 = H, 1-12C alkyl or Ph'; R9 = H or 1-12C alkyl; R8 + R9 = 4-7C alkylene (optionally interrupted by O, S, SO, SO2 or NR10); R10 = H or 1-12C alkyl; R11 = halo, U', 2-4C alkenyl, OH, OU', SH, SU', SOU', SO2U', OSO2U', NH2, NHU, NU2, SO2NHU', SO2NU2, NO2, CN, COOH, COOU, OCOU, NHCOU, COT, Ph', OPh', CH2Ph' or OCH2Ph'; X1-X4 = O or S; p, n = 0-2; q = 0 or 1; T = 1-6C alkyl; T' = T or 1-6C haloalkyl; U = 1-4C alkyl; U' = U or 1-4C haloalkyl; V = 1-3C alkyl or 1-3C haloalkyl. Provided that when: (1) R is H, CN or NC, n is 0; (2) R is OH or NR8R9, n is 1 or 2; and (3) Cyc may be substituted by 1-3 R3 when no N-halo groups are present. An Independent claim is included for the preparation of (I).