New 4-pyridylcarbonyl-cyclohexene-dione derivatives, useful as both total and selective herbicides and effective against mono- and di-cotyledonous weeds, for use on e.g. cereals, cotton, soya, sugar beet/cane and rape

    公开(公告)号:DE10256364A1

    公开(公告)日:2003-06-18

    申请号:DE10256364

    申请日:2002-12-03

    Abstract: 5-Amino-4-(pyridinylcarbonyl)-cyclohexene-1,3-dione derivatives (I) and their salts, all isomers and tautomers are new. 5-Amino-4-(pyridinylcarbonyl)-cyclohexene-1,3-dione derivatives of formula (I) and their salts, all isomers and tautomers are new. R1 = H, 1-12C alkyl, 2-12C alkenyl or alkynyl, 3-12C allenyl, 3-12C cycloalkyl, R3-(1-12C alkylene or 2-12C alkenylene) where alkylene and alkenylene may be interrupted by oxygen, S(O)n, NR21 or CO and substituted by R4, or phenyl (optionally substituted 1-5 times by R5), 3-12 membered, mono- or bi-cyclic ring system, aromatic, partly or fully saturated, optionally containing 1-5 heteroatoms (nitrogen, oxygen and/or sulfur) or 1-2 carbonyl, and optionally substituted by 1-3 R6, with the system attached through a C or N atom, directly or via a 1-6C alkylene or alkenylene chain, itself optionally interrupted by oxygen or S(O)n and/or substituted by R7, to which NR1R2 is attached, and substituents on N are other than halo, or cyano, C(X1)X2R8, C(X3)NR9R10, 1-12C alkoxy or alkylthio; R2 = H, cyano, 1-12C (halo)alkyl, 2-12C (halo)alkenyl or (halo)alkynyl, 3-12C allenyl, 3-12C cycloalkyl, R11-(1-12C alkylene or 2-12C alkenylene) where alkylene and alkenylene may be interrupted by oxygen, or S(O)n and substituted by R12, or R2 and R1 are together 2-12C alkylene or alkenylene (optionally interrupted by 1-3 O, S(O)n, NR13 or CX4) and optionally substituted by 1-4 R14, or NR1R2 is pyrrolyl, pyrazolyl, imidazolyl, triazolyl or tetrazolyl, all but the last optionally substituted by 1-3 R15; n = 0-2; X1 = O or S; X2 = bond, O or S; X3 = O, S or NR21; X4 = O, S, OCH2CH2O or OCH2CH2CH2O; and Q = N or N -O . The full definitions are given in the DEFINITIONS (Full Definitions) Field. An Independent claim is also included for a method for making (I) by reacting the corresponding 5-halo compound (II) with HNR1R2, or its alkali or alkaline earth metal salt.

    New 5-thiol-4-pyridylcarbonyl-cyclohexene-dione derivatives, useful as herbicides and plant growth inhibitors, with improved leaching properties and selectivity

    公开(公告)号:DE10256354A1

    公开(公告)日:2003-06-18

    申请号:DE10256354

    申请日:2002-12-03

    Abstract: 5-substituted thiol-4-(pyridinylcarbonyl)-cyclohexene-1,3-dione derivatives (I) and their salts, all isomers and tautomers are new. 5-substituted thiol- 4-(pyridinylcarbonyl)-cyclohexene-1,3-dione derivatives of formula (I) and their salts, all isomers and tautomers are new. R = 1-12C alkyl, 2-12C alkenyl or alkynyl, 3-12C allenyl, 3-12C cycloalkyl, 5-12C cycloalkenyl, R1-(1-12C alkylene or 2-12C alkenylene) (where alkylene and alkenylene may be interrupted by oxygen, S(O)p, or CO and substituted by one or more R2, or phenyl (optionally substituted 1-5 times by R11)), 3-12 membered aromatic or partially or fully saturated mono- or bi-cyclic ring system, (optionally containing 1-5 heteroatoms (nitrogen, oxygen and/or sulfur)) or 1-2 carbonyl (optionally substituted by one or more R3), with the ring system attached, via C or N atoms, directly or through a 1-6C alkylene or alkenylene linker (optionally interrupted by O or S(O)p and/or substituted by R4) to the S of S(O)nR, and substituents on N are other than halo, or halo, 1-12C alkylthio, cyano, C(X1)R6, C(X2)X3R7, C(X4)NR8R9, or, if n = 0, also hydrogen, cyano or isocyano or hydroxy, or NR80R90 when n = 1 or 2; Z1 = 1-3C alkyl; Y = hydrogen, chloro, bromo or 1-2C (halo)alkyl; n and p = 0-2; q = 0 or 1; and X1-X4 = oxygen or sulfur; The full definitions are given in the DEFINITIONS (Full Definitions) Field. An Independent claim is also included for the preparation of (I).

    DERIVADOS DE N-FENIL-((4-PIRIDIL)-AZINIL-)-AMINA COPMO AGENTES FITOPROTECTORES.

    公开(公告)号:ES2323502T3

    公开(公告)日:2009-07-17

    申请号:ES04723281

    申请日:2004-03-25

    Abstract: Un método de controlar y prevenir una infestación de plantas de cultivo por microorganismos fitopatógenos, que comprende la aplicación a la planta o partes de plantas o al emplazamiento de la misma, como ingrediente activo, de un derivado de N-fenil-[(4-piridil)-azinil]-amina de fórmula I ** ver fórmula** en la que A y A'' ambos son N o A y A'' ambos son CH o A es CH y A'' es N; j es 0 o 1 R 1 es a) hidrazino, que está sin sustituir o sustituido una a tres veces con alquilo opcionalmente sustituido y/o acilo opcionalmente sustituido, b) ciclohexilamino, tetrahidro-4H-piranil-4-amino, pirrolidin-3-amino, 2- o 3-tetrahidro- furilamino, todos opcionalmente sustituidos con amino, hidroxi, alcoxi, alquilo o alcoxialquilo, c) piperazinilo que está opcionalmente sustituido con amino, amino-alquil-C 1-C 6, hidroxi, alcoxi, alquilo o alcoxialquilo, d) morfolinilo que está opcionalmente sustituido con amino, amino-alquil-C1-C6, hidroxi, alcoxi, alquilo o alcoxialquilo, e) amino o mono- o di-(alquil C 1-C 6)amino en el que los restos alquilo C 1-C 6 están sin sustituir o sustituidos con uno o más (preferentemente 1 a 3, especialmente 1 o 2) sustituyentes seleccionados independientemente del grupo que consiste en amino sin sustituir, N-mono- o N,N-di-(alquil C1-C6)-amino, (alcoxi C1-C6)-alcoxi C1-C6, alcoxi (C1-C6)carbonilamino, hidroxi-alcoxi(C1-C6)carbonilamino, alcoxi-C1-C6-alcoxi-C1-C6-carbonilamino, morfolinilo, hidroxialquil-C 1-C 6-amino, ciano, halógeno, oxo, hidroximino, alcoximino, hidrazono opcionalmente sustituido, alquenilo C 1-C 6, alquinilo C 1-C 6, guanidilo, alcanoilamino C 1-C 6, hidroxialcanoil-C 1-C 6-amino, alcoxi-C 1-C 6-alcanoil- C1-C6-amino, haloalcanoil-C1-C6-amino, alquil-C1-C6-aminocarbonilamino, hidroxialquila-C1-C6-minocarbonilamino, alcoxi-C1-C6-alquil-C1-C6-aminocarbonilamino, amidino, dialquil-C1-C6-amino-ciclohexilo, carboxi, alcoxi-C1- C6-carbonilo, hidroxialcoxi-C1-C6-carbonilo, alcoxi-C1-C6-alcoxi-C1-C6-carbonilo, alquil-C1-C6-carbonildioxi (= alcoxi-C 1-C 6-carboniloxi), hidroxialcoxi-C 1-C 6-carboniloxi, alcoxi-C 1-C 6-alcoxi-C 1-C 6-carboniloxi, alcanoiloxi C 1-C 6, haloalcanoiloxi C 1-C 6, hidroxialcanoiloxi C 1-C 6, alcoxi-C 1-C 6-alcanoil-C 1-C 6-oxi, carbamoilo, N-mono- o N,N-dialquil-C1-C6-carbamoilo, N-(hidroxialquil C1-C6)carbamoilo, N-alquil-C1-C6-N-hidroxialquil-C1-C6-carbamoilo, N,Ndi-(hidroxialquil C1-C6)-carbamoilo, N-hidroxi-carbamoilo, hidroxi, alcoxi C1-C6, alqueniloxi C1-C6, alquiniloxi C1- C6, haloalcoxi C1-C6, alquiltio C1-C6, alquilsulfoxilo C1-C6, alquilsulfonilo C1-C6, alcoxisililo C1-C6, 4-tetrahidro-4Hpiranilo, 3-pirrolidinilo, 2- o 3-tetrahidrofurilo, 2- o 3-dihidrofurilo, piperazinilo, alcanoil-C 1-C 6-piperazinilo (incluido formilpiperazinilo), heteroarilo opcionalmente sustituido y heteroariloxi opcionalmente sustituido, f) alcanoilamino opcionalmente sustituido, alquenoilamino opcionalmente sustituido, alquinoilamino opcionalmente sustituido, mono- o di-alquilaminocarbonilamino opcionalmente sustituido, alcoxicarbonilamino opcionalmente sustituido, mono- o di-alquilaminosulfonilamino opcionalmente sustituido, mono- o di-alquilaminosulfoxilamino opcionalmente sustituido, g) N-(alquil opcionalmente sustituido)-N-(alcanoil C1-C6 opcionalmente sustituido)-amino, h) N-(alquil opcionalmente sustituido)-N-(alcoxicarbonil opcionalmente sustituido)-amino, i) N-(alquil opcionalmente sustituido)-N-(N'',N''-mono- o di-[alquil opcionalmente sustituido]-aminocarbonil)amino, j) N=C(R7,R8) en el que R7 es hidrógeno, alquilo, amino, mono- o di-alquilamino y R8 es amino, mono- o dialquilamino o en el que R7 y R8, junto con el átomo de carbono de unión, forman un anillo saturado de cinco a siete miembros con 0, 1 o 2 átomos de nitrógeno del anillo que está opcionalmente sustituido con uno o más sustituyentes, preferentemente 1 a 3 sustituyentes, especialmente alquilo C 1-C 6, k) un grupo heterociclilo de 4 a 7 miembros opcionalmente sustituido que contiene uno o dos átomos de nitrógeno, oxígeno o azufre pero por lo menos un átomo de nitrógeno mediante el cual el anillo de heterociclilo se une al resto de la molécula; R2 es hidrógeno, alquilo C1-C4, alquenilo C3-C4, alquinilo C3-C4, -CH2OR16, -CH2SR16, -C(O)R16, -C(O)OR16, SO2R16, SOR16 o SR16; en los que R16 es alquilo C1-C8, alcoxialquilo C1-C8, haloalquilo C1-C8 o fenilalquilo C1-C2, en el que el fenilo puede estar sustituido con hasta tres grupos seleccionados de halo o alquilo C 1-C 4; R 3 es hidrógeno, halógeno, alquilo C 1-C 4, haloalquilo C 1-C 4, haloalcoxi C 1-C 4; hidroxi, mercapto, ciano o alcoxi C 1-C 4; R 4 y R 5 son, independientemente uno de otro, halógeno, alquilo opcionalmente sustituido, alquenilo opcionalmente sustituido, alquinilo opcionalmente sustituido, arilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, alcoxi opcionalmente sustituido, aciloxi opcionalmente sustituido, alqueniloxi opcionalmente sustituido, alquiniloxi opcionalmente sustituido, ariloxi opcionalmente sustituido, heteroariloxi opcionalmente sustituido, acilamino opcionalmente sustituido, tioalquilo opcionalmente sustituido, COOR 17, CONR 18R 19, S(O) kR 20, SO 2NR 21R 22, NR 23R 24, NR 25SO 2R 26, NO 2, CN, C(=O)R 27, C(=NOR 28)R 29 R 6 es hidrógeno, halógeno, alquilo opcionalmente sustituido, alquenilo opcionalmente sustituido, alquinilo opcionalmente sustituido, arilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, alcoxi opcionalmente sustituido, aciloxi opcionalmente sustituido, alqueniloxi opcionalmente sustituido, alquiniloxi opcionalmente sustituido, ariloxi opcionalmente sustituido, heteroariloxi opcionalmente sustituido, acilamino opcionalmente sustituido, tioalquilo opcionalmente sustituido, COOR 17, CONR 18R 19, S(O) kR 20, SO 2NR 21R 22, NR 23R 24, NR 25SO 2R 26, NO 2, CN, C(=O)R 27, C(=NOR 28)R 29 o R 4 y R 5 o R 5 y R 6 juntos forman un sistema de anillo carbocíclico saturado o insaturado de cinco a seis miembros o un sistema de anillo heterocíclico o heteroaromático de cinco a seis miembros que está opcionalmente sustituido y contiene uno a tres heteroátomos seleccionados de O, N o S; k es 0, 1 o 2 y R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 y R29 son independientemente H o alquilo opcionalmente sustituido o arilo opcionalmente sustituido; o una sal del mismo a condición de que cuando A es CH y A'' es N entonces R 1 no es un grupo heterociclilo opcionalmente sustituido de 5 o 6 miembros unido por el N que contiene dos átomos de nitrógeno adyacentes como los únicos heteroátomos en el anillo heterocíclico.

    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

    公开(公告)号:DE10256367A1

    公开(公告)日:2003-06-26

    申请号:DE10256367

    申请日:2002-12-03

    Abstract: 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).

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