AR102294A1 - Compuestos herbicidas, composiciones y un método de control de malezas que los emplea - Google Patents

Compuestos herbicidas, composiciones y un método de control de malezas que los emplea

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Publication number
AR102294A1
AR102294A1 ARP150103350A ARP150103350A AR102294A1 AR 102294 A1 AR102294 A1 AR 102294A1 AR P150103350 A ARP150103350 A AR P150103350A AR P150103350 A ARP150103350 A AR P150103350A AR 102294 A1 AR102294 A1 AR 102294A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
fluoroalkyl
fluoroalkoxy
nitro
Prior art date
Application number
ARP150103350A
Other languages
English (en)
Inventor
Jane Dale Suzanna
Briggs Emma
Black Janice
Stuart Cloudsdale Ian
James Willetts Nigel
Steven Wailes Jeffrey
Hachisu Shuji
Joseph Hennessy Alan
Original Assignee
Syngenta Participations Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of AR102294A1 publication Critical patent/AR102294A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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Abstract

Estos compuestos son adecuados para uso como herbicidas, por lo tanto, también se refiere a un método para controlar malezas, especialmente malezas monocotiledóneas herbáceas, en cultivos de plantas útiles, que comprende aplicar un compuesto de los mencionados, o una composición herbicida que comprende dicho compuesto, a las plantas o a su emplazamiento. Reivindicación 1: Un compuesto de fórmula (1), donde: R¹ se selecciona del grupo que consiste en metilo, etilo, n-propilo, ciclopropilo, trifluorometilo, vinilo, etinilo, flúor, cloro, bromo, metoxi, difluorometoxi y trifluorometoxi; y tanto (a): R² es R²A y R³ es R³A; o (b): R² es R²B y R³ es R³B; donde: R²A se selecciona del grupo que consiste en hidrógeno, metilo, etilo, n-propilo, isopropilo, ciclopropilo, fluoroalquilo C₁₋₂, vinilo, prop-1-enilo, prop-1-inilo, -CºC-R²AA, halógeno y (fluoroalquil C₁₋₂)-metoxi-; donde R²AA se selecciona del grupo que consiste en hidrógeno, flúor, cloro, trifluorometilo, etilo y ciclopropilo; o R²A es fenilo opcionalmente sustituido por 1, 2 ó 3 sustituyentes seleccionados independientemente del grupo que consiste en halógeno, alquilo C₁₋₂, fluoroalquilo C₁₋₂, metoximetilo, vinilo, etinilo, alcoxi C₁₋₃, fluoroalcoxi C₁₋₂, -S(O)ₚ-metilo, ciano o nitro, siempre que tanto uno o ninguno (es decir, no más que uno) de estos sustituyentes opcionales sean metoximetilo, vinilo, etinilo, -S(O)ₚ-metilo o nitro; o R²A es un heteroarilo monocíclico opcionalmente sustituido por 1, 2 ó 3 sustituyentes seleccionados independientemente del grupo que consiste en halógeno, alquilo C₁₋₂, fluoroalquilo C₁₋₂, metoximetilo, vinilo, etinilo, alcoxi C₁₋₃, fluoroalcoxi C₁₋₂, -S(O)ₚ-metilo, ciano y nitro, siempre que tanto uno o ninguno (es decir, no más que uno) de estos sustituyentes opcionales sean metoximetilo, vinilo, etinilo, -S(O)ₚ-metilo o nitro; R³A se selecciona del grupo que consiste en hidrógeno, metilo, flúor y cloro; y donde R²B es hidrógeno, metilo o flúor; y tanto R³B es fenilo opcionalmente sustituido por 1, 2 ó 3 sustituyentes seleccionados independientemente del grupo que consiste en halógeno, alquilo C₁₋₂, fluoroalquilo C₁₋₂, metoximetilo, vinilo, etinilo, alcoxi C₁₋₂, fluoroalcoxi C₁₋₂, -S(O)ₚ-metilo, ciano y nitro, siempre que tanto uno o ninguno (es decir, no más que uno) de estos sustituyentes opcionales sean metoximetilo, vinilo, etinilo, -S(O)ₚ-metilo o nitro; o R³B es un heteroarilo monocíclico opcionalmente sustituido por 1, 2 ó 3 sustituyentes seleccionados independientemente del grupo que consiste en halógeno, alquilo C₁₋₂, fluoroalquilo C₁₋₂, metoximetilo, vinilo, etinilo, alcoxi C₁₋₂, fluoroalcoxi C₁₋₂, -S(O)ₚ-metilo, ciano y nitro, siempre que tanto uno o ninguno (es decir, no más que uno) de estos sustituyentes opcionales sean metoximetilo, vinilo, etinilo, -S(O)ₚ-metilo o nitro; R⁴ se selecciona del grupo que consiste en hidrógeno, metilo, etilo, n-propilo, ciclopropilo, trifluorometilo, vinilo, etinilo, flúor, cloro, bromo, alcoxi C₁₋₃, fluoroalcoxi C₁₋₂, alcoxi C₁₋₂-alcoxi C₁₋₃-, o fluoroalcoxi C₁-alcoxi C₁₋₃-; R⁵, R⁶ y R⁷ se seleccionan independientemente del grupo que consiste en hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₃, alquinilo C₂₋₃, haloalquilo C₁₋₂ y alcoxi C₁₋₂-alquilo C₁₋₂-; R⁸ y R⁹ se seleccionan independientemente del grupo que consiste en hidrógeno, flúor y alquilo C₁₋₃; R¹⁰ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, alquil C₁₋₆ ciano, alcoxi C₁₋₆-alquilo C₁₋₆-, alcoxi C₁₋₆-alquenilo C₂₋₆-, alcoxi C₁₋₆-alquinilo C₂₋₆-, alqueniloxi C₁₋₆-alquilo C₁₋₆-, alcoxi C₁₋₆-alcoxi C₂₋₃-alquilo C₂₋₃-, alquilcarbonilo C₁₋₆- y alquilcarbonilo C₁₋₆-alquilo C₁₋₆-; R¹¹ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, alquilciano C₁₋₆, alcoxi C₁₋₆-alquilo C₁₋₆-, alcoxi C₁₋₆-alquenilo C₂₋₆-, alcoxi C₁₋₆-alquinilo C₂₋₆-, alqueniloxi C₁₋₆-alquilo C₁₋₆-, alcoxi C₁₋₆-alcoxi C₂₋₃-alquilo C₂₋₃-, alquilcarbonilo C₁₋₆-, alquilcarbonilo C₁₋₆-alquilo C₁₋₆-; o R¹¹ es -(CRR)ₙ-X¹-R¹³ donde X¹ es un enlace, -(CH=CH)- o -(C=O)- y donde R y R se seleccionan independientemente de hidrógeno y metilo o juntos de una cadena alquileno C₂₋₃; o R¹⁰ y R¹¹ forman juntos un heterociclo de cuatro a seis miembros, donde el heterociclo comprende uno o más heteroátomos seleccionados del grupo que consiste en oxígeno, nitrógeno y azufre; el heterociclo es opcionalmente sustituido por uno o más R¹² independientes; R¹² se selecciona del grupo que consiste en halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, alcoxi C₁₋₆-, nitro, -(CO)OR¹⁴, ciano, fenilo, piridilo; R¹³ es un sistema de anillo mono o bicíclico de tres a diez miembros, que puede ser aromático, saturado o parcialmente saturado y puede contener de 1 a 4 heteroátomos cada uno seleccionado independientemente del grupo que consiste en nitrógeno, oxígeno y azufre siendo el sistema de anillo opcionalmente sustituido por uno o más sustituyentes R¹²; R¹⁴ es H o alquilo C₁₋₆; n = 0, 1, 2, 3 ó 4; p = 0, 1 ó 2; y G es hidrógeno; un metal agrícolamente aceptable, o un grupo sulfonio o amonio agrícolamente aceptable; o G es -C(Xᵃ)-Rᵃ, -C(Xᵇ)-Xᶜ-Rᵇ, -C(Xᵈ)-N(Rᶜ)-Rᵈ, -SO₂-Rᵉ, -P(Xᵉ)(Rᶠ)-Rᵍ, -CH₂-Xᶠ-R¹¹; o fenil-CH₂- o fenil-CH(alquilo C₁₋₂)- (en cada uno de los cuales el fenilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₂, fluoroalquilo C₁, alcoxi C₁₋₂, fluoroalcoxi C₁, flúor, cloro, bromo, ciano o nitro), o heteroaril-CH₂- o heteroaril-CH(alquilo C₁₋₂)- (en cada uno de los cuales el heteroarilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₂, fluoroalquilo C₁, alcoxi C₁₋₂, fluoroalcoxi C₁, flúor, cloro, bromo, ciano o nitro), o fenil-C(O)-CH₂- (donde el fenilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₂, fluoroalquilo C₁, alcoxi C₁₋₂, fluoroalcoxi C₁, flúor, cloro, bromo, ciano o nitro); o alcoxi C₁₋₆-C(O)-CH₂-, alquil C₁₋₆-C(O)-CH₂-, alcoxi C₁₋₆-C(O)-CH=CH-, alquen C₂₋₇-1-il- CH₂-, alquen C₂₋₇-1-il-CH(alquilo C₁₋₂)-, fluoroalquen C₂₋₄-1-il-CH₂-, alquin C₂₋₇-1-il-CH₂-, o alquin C₂₋₇-1-il- CH(alquilo C₁₋₂)-; donde Xᵃ, Xᵇ, Xᶜ, Xᵈ, Xᵉ y Xᶠ son independientemente unos de otros oxígeno o azufre; y donde Rᵃ es H, alquilo C₁₋₂₁, alquenilo C₂₋₂₁, alquinilo C₂₋₁₈, fluoroalquilo C₁₋₁₀, cianoalquilo C₁₋₁₀, nitroalquilo C₁₋₁₀, aminoalquilo C₁₋₁₀, alquilamino C₁₋₅alquilo C₁₋₅, dialquilamino C₂₋₈alquilo C₁₋₅, cicloalquil C₃₋₇alquilo C₁₋₅, alcoxi C₁₋₅alquilo C₁₋₅, alqueniloxi C₃₋₅alquilo C₁₋₅, alquiniloxi C₃₋₅alquilo C₁₋₅, alquil C₁₋₅tioalquilo C₁₋₅, alquil C₁₋₅sulfinilalquilo C₁₋₅, alquil C₁₋₅sulfonilalquilo C₁₋₅, alquil C₂₋₈idenaminoxialquilo C₁₋₅, alquil C₁₋₅carbonilalquilo C₁₋₅, alcoxi C₁₋₅carbonilalquilo C₁₋₅, aminocarbonilalquilo C₁₋₅, alquilamino C₁₋₅carbonilalquilo C₁₋₅, dialquilamino C₂₋₈carbonilalquilo C₁₋₅, alquil C₁₋₅carbonilaminoalquilo C₁₋₅, N-alquil C₁₋₅carbonil-N-alquilamino C₁₋₅alquilo C₁₋₅, trialquil C₃₋₆sililalquilo C₁₋₅, fenilalquilo C₁₋₅ (donde el fenilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), heteroarilalquilo C₁₋₅ (donde el heteroarilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), fluoroalquenilo C₂₋₅, cicloalquilo C₃₋₈; fenilo o fenilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; o heteroarilo o heteroarilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; Rᵇ es alquilo C₁₋₁₈, alquenilo C₃₋₁₈, alquinilo C₃₋₁₈, fluoroalquilo C₂₋₁₀, cianoalquilo C₁₋₁₀, nitroalquilo C₁₋₁₀, aminoalquilo C₂₋₁₀, alquilamino C₁₋₅alquilo C₁₋₅, dialquilamino C₂₋₈alquilo C₁₋₅, cicloalquil C₃₋₇alquilo C₁₋₅, alcoxi C₁₋₅alquilo C₁₋₅, alqueniloxi C₃₋₅alquilo C₁₋₅, alquiniloxi C₃₋₅alquilo C₁₋₅, alquil C₁₋₅tioalquilo C₁₋₅, alquil C₁₋₅sulfinilalquilo C₁₋₅, alquil C₁₋₅sulfonilalquilo C₁₋₅, alquil C₂₋₈idenaminoxialquilo C₁₋₅, alquil C₁₋₅carbonilalquilo C₁₋₅, alcoxi C₁₋₅carbonilalquilo C₁₋₅, aminocarbonilalquilo C₁₋₅, alquilamino C₁₋₅carbonilalquilo C₁₋₅, dialquilamino C₂₋₈carbonilalquilo C₁₋₅, alquil C₁₋₅carbonilaminoalquilo C₁₋₅, N-alquil C₁₋₅carbonil-N-alquilamino C₁₋₅alquilo C₁₋₅, trialquil C₃₋₆sililalquilo C₁₋₅, fenilalquilo C₁₋₅ (donde el fenilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), heteroarilalquilo C₁₋₅ (donde el heteroarilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), fluoroalquenilo C₃₋₅, cicloalquilo C₃₋₈; fenilo o fenilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; o heteroarilo o heteroarilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; y Rᶜ y Rᵈ son cada uno independientemente uno del otro hidrógeno, alquilo C₁₋₁₀, alquenilo C₁₋₁₀, alquinilo C₁₋₁₀, fluoroalquilo C₂₋₁₀, cianoalquilo C₁₋₁₀, nitroalquilo C₁₋₁₀, aminoalquilo C₁₋₁₀, (alquilamino C₁₋₅)-(alquilo C₁₋₅), (dialquilamino C₂₋₈)-(alquilo C₁₋₅), (cicloalquil C₃₋₇)-(alquilo C₁₋₅), (alcoxi C₁₋₅)-(alquilo C₁₋₅), (alqueniloxi C₃₋₅)-(alquilo C₁₋₅), (alquiniloxi C₁₋₅)-(alquilo C₁₋₅), (alquiltio C₁₋₅)-(alquilo C₁₋₅), (alquilsulfinil C₁₋₅)-(alquilo C₁₋₅), (alquilsulfonil C₁₋₅)-(alquilo C₁₋₅), (alquilidenaminoxi C₂₋₈)-(alquilo C₁₋₅), (alquil C₁₋₅)carbonil-(alquilo C₁₋₅), (alcoxi C₁₋₅)carbonil-(alquilo C₁₋₅), aminocarbonil-(alquilo C₁₋₅), (alquilamino C₁₋₅)carbonil-(alquilo C₁₋₅), (dialquilamino C₂₋₈)carbonil-(alquilo C₁₋₅), (alquil C₁₋₅)carbonilamino-(alquilo C₁₋₅), N-(alquil C₁₋₅)carbonil-N-(alquilamino C₂₋₅)alquilo, (trialquilsilil C₃₋₆)-(alquilo C₁₋₅), fenilalquilo C₁₋₅ (donde el fenilo está opcionalmente sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquiltio C₁₋₃, alquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, halógeno, ciano, o nitro), heteroaril-(alquilo C₁₋₅) (donde el heteroarilo está opcionalmente sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquiltio C₁₋₃, alquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, halógeno, ciano, o nitro), fluoroalquenilo C₂₋₅, cicloalquilo C₃₋₈; fenilo o fenilo sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilo o heteroarilo sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilamino o heteroarilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; diheteroarilamino o diheteroarilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; fenilamino o fenilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o con nitro; difenilamino o difenilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; o cicloalquilamino C₃₋₇, di(cicloalquil C₃₋₇)amino o cicloalcoxi C₃₋₇; o Rᶜ y Rᵈ, junto con el nitrógeno al que están enlazados, forman un anillo de 4, 5, 6 ó 7 (p. ej., 5 ó 6) miembros no sustituido que contiene opcionalmente un heteroátomo seleccionado entre O ó S; y Rᵉ es alquilo C₁₋₁₀, alquenilo C₂₋₁₀, alquinilo C₂₋₁₀, fluoroalquilo C₁₋₁₀, cianoalquilo C₁₋₁₀, nitroalquilo C₁₋₁₀, aminoalquilo C₁₋₁₀, alquilamino C₁₋₅alquilo C₁₋₅, dialquilamino C₂₋₈alquilo C₁₋₅, cicloalquil C₃₋₇alquilo C₁₋₅, alcoxi C₁₋₅alquilo C₁₋₅, alqueniloxi C₃₋₅alquilo C₁₋₅, alquiniloxi C₃₋₅alquilo C₁₋₅, alquil C₁₋₅tioalquilo C₁₋₅, alquil C₁₋₅sulfinilalquilo C₁₋₅, alquil C₁₋₅sulfonilalquilo C₁₋₅, alquil C₂₋₈idenaminoxialquilo C₁₋₅, alquil C₁₋₅carbonilalquilo C₁₋₅, alcoxi C₁₋₅carbonilalquilo C₁₋₅, aminocarbonilalquilo C₁₋₅, alquilamino C₁₋₅carbonilalquilo C₁₋₅, dialquilamino C₂₋₈carbonilalquilo C₁₋₅, alquil C₁₋₅carbonilaminoalquilo C₁₋₅, N-alquil C₁₋₅carbonil-N-alquilamino C₁₋₅alquilo C₁₋₅, trialquil C₃₋₆sililalquilo C₁₋₅, fenilalquilo C₁₋₅ (donde el fenilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), heteroarilalquilo C₁₋₅ (donde el heteroarilo está opcionalmente sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, halógeno, ciano, o nitro), fluoroalquenilo C₂₋₅, cicloalquilo C₃₋₈; fenilo o fenilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilo o heteroarilo sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilamino o heteroarilamino sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; diheteroarilamino o diheteroarilamino sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; fenilamino o fenilamino sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; difenilamino o difenilamino sustituido por 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; o cicloalquil C₃₋₇amino, di(cicloalquil C₃₋₇)amino, cicloalcoxi C₃₋₇, alcoxi C₁₋₁₀, fluoroalcoxi C₁₋₁₀, alquilamino C₁₋₅ o di(alquil C₁₋₄)amino; Rᶠ y Rᵍ son cada uno independientemente uno del otro alquilo C₁₋₁₀, alquenilo C₂₋₁₀, alquinilo C₂₋₁₀, alcoxi C₁₋₁₀, fluoroalquilo C₁₋₁₀, cianoalquilo C₁₋₁₀, nitroalquilo C₁₋₁₀, aminoalquilo C₁₋₁₀, (alquilamino C₁₋₅)-(alquilo C₁₋₅), (dialquilamino C₂₋₈)-(alquilo C₁₋₅), (cicloalquil C₃₋₇)-(alquilo C₁₋₅), (alcoxi C₁₋₅)-(alquilo C₁₋₅), (alqueniloxi C₃₋₅)-(alquilo C₁₋₅), (alquiniloxi C₃₋₅)-(alquilo C₁₋₅), (alquiltio C₁₋₅)-(alquilo C₁₋₅), (alquilsulfinil C₁₋₅)-(alquilo C₁₋₅), (alquilsulfonil C₁₋₅)-(alquilo C₁₋₅), (alquilidenaminoxi C₂₋₈)-(alquilo C₁₋₅), (alquil C₁₋₅)carbonil-(alquilo C₁₋₅), (alcoxi C₁₋₅)carbonil-(alquilo C₁₋₅), aminocarbonil-(alquilo C₁₋₅), (alquilamino C₁₋₅)carbonil-(alquilo C₁₋₅), (dialquilamino C₂₋₈)carbonil-(alquilo C₁₋₅), (alquil C₁₋₅)carbonilamino-(alquilo C₁₋₅), N-(alquil C₁₋₅)carbonil-N-(alquilamino C₂₋₅) alquilo, (trialquilsilil C₃₋₆)-(alquilo C₁₋₅), fenilalquilo C₁₋₅ (donde el fenilo está opcionalmente sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquiltio C₁₋₃, alquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, halógeno, ciano o nitro), heteroaril-(alquilo C₁₋₅) (donde el heteroarilo está opcionalmente sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, alquiltio C₁₋₃, alquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, halógeno, ciano o nitro), fluoroalquenilo C₂₋₅, cicloalquilo C₃₋₈; fenilo o fenilo sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilo o heteroarilo sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃ fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; heteroarilamino o heteroarilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; diheteroarilamino o diheteroarilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; fenilamino o fenilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; difenilamino o difenilamino sustituido con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno, ciano o nitro; o cicloalquilamino C₁₋₃, di(cicloalquil C₁₋₃)amino, cicloalcoxi C₃₋₇, fluoroalcoxi C₃₋₇, alquilamino C₁₋₅ o di(alquil C₁₋₄)amino; o benciloxi o fenoxi, donde los grupos bencilo y fenilo están a su vez opcionalmente sustituidos con 1, 2 ó 3 de, independientemente, alquilo C₁₋₃, fluoroalquilo C₁₋₃, alcoxi C₁₋₃, fluoroalcoxi C₁₋₃, halógeno,
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