AR098484A1 - Insecticidas de 1-aril-3-alquilpirazol - Google Patents

Insecticidas de 1-aril-3-alquilpirazol

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Publication number
AR098484A1
AR098484A1 ARP140104359A ARP140104359A AR098484A1 AR 098484 A1 AR098484 A1 AR 098484A1 AR P140104359 A ARP140104359 A AR P140104359A AR P140104359 A ARP140104359 A AR P140104359A AR 098484 A1 AR098484 A1 AR 098484A1
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Argentina
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alkyl
ring
substituted
unsubstituted
cyano
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ARP140104359A
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English (en)
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Khaled Ahmad Omar
Francis Pahutski Thomas Jr
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Du Pont
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Publication of AR098484A1 publication Critical patent/AR098484A1/es

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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
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    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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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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    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • 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
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • 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
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • 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
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Veterinary Medicine (AREA)
  • Soil Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

También se describen las composiciones que contienen los compuestos y los métodos para controlar una plaga invertebrada; el método comprende la etapa de poner la plaga invertebrada o su ambiente en contacto con cantidad biológicamente eficaz de un compuesto o una composición de la presente. Reivindicación 1: Un compuesto seleccionado de la fórmula (1), un N-óxido o una sal del estos, caracterizado porque Q es un resto de fórmula (2); R¹ es alquilo C₁₋₆, alquenilo C₂₋₆ o alquinilo C₂₋₆, cada uno insustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, C(X)R⁵ᵃ, C(O)OR⁶ᵃ, C(X)NR⁷ᵃR⁸ᵃ, NR⁹ᵃR¹⁰ᵃ, OR¹²ᵃ, S(O)ₙR¹¹ᵃ, SO₂NR⁹ᵃR¹⁰ᵃ, Si(R¹⁴)₃ y Z¹; o R¹ es un anillo de 3 a 10 miembros totalmente o parcialmente saturado o un sistema anular de 7 a 11 miembros totalmente o parcialmente saturado, cada anillo o sistema anular contiene miembros anulares seleccionados de átomos de carbono y hasta 4 heteroátomos independientemente seleccionados de hasta 2 O, hasta 2 S, y hasta 4 N, en donde hasta 3 miembros anulares de los átomos de carbono son independientemente seleccionados C(=O) y C(=S) y los miembros anulares de los átomos de azufre son independientemente seleccionados de S, S(O) o S(O)₂, cada anillo o sistema anular insustituido o sustituido con 1 a 4 R⁴; Z es fenilo sustituido con 1 a 3 R⁴; o Z es un anillo heteroaromático de 5 ó 6 miembros o un sistema anular bicíclico heteroaromático de 8 a 10 miembros, cada anillo o sistema anular no sustituido o sustituido con 1 a 3 R⁴; Z¹ es un anillo de 3 a 10 miembros o un sistema anular de 7 a 11 miembros, cada anillo o sistema anular contiene miembros anulares seleccionados de átomos de carbono y hasta 4 heteroátomos independientemente seleccionados de hasta 2 O, hasta 2 S, y hasta 4 N, en donde hasta 3 miembros anulares de los átomos de carbono son independientemente seleccionados C(=O) y C(=S) y los miembros anulares de los átomos de azufre son independientemente seleccionados de S, S(O) o S(O)₂, cada anillo o sistema anular insustituido o sustituido con 1 a 4 R⁴; R²ᵃ y R²ᶜ son, independientemente, cada uno, H, halógeno, ciano, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, OR¹² o S(O)ₙR¹¹; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con por lo menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; R²ᵇ y R²ᵈ son, independientemente cada uno, H, halógeno, ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con por lo menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R⁴; J¹ es un enlace directo, -C(R³ᵃR³ᵇ)- o -C(R³ᵃR³ᵇ)C(R³ᵃR³ᵇ)-; J² es un enlace directo o -C(R³ᶜR³ᵈ)-; M es -C(R³ᵉ)(A)-, -N(A¹)-, -O- o -S(O)ₙ-; A es halógeno, ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C₁₋₄, haloalquilo C₁₋₄, C₍O₎R⁵ᵃ, C(O)OR⁶ᵃ, C(O)NR⁷ᵃR⁸ᵃ, NR⁹ᵃR¹⁰ᵃ, OR¹²ᵃ y S(O)ₙR¹¹ᵃ; o fenilo, un anillo heteroaromático de 5 ó 6 miembros o un sistema anular heteroaromático de 7 a 11 miembros, cada anillo o sistema anular no sustituido o sustituido con 1 a 3 R⁴; A¹ es ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, alquilo C₁₋₄, haloalquilo C₁₋₄, C₍O₎R⁵ᵃ, C(O)OR⁶ᵃ, C(O)NR⁷ᵃR⁸ᵃ, NR⁹ᵃR¹⁰ᵃ, OR¹²ᵃ y S(O)ₙR¹¹ᵃ; o fenilo, un anillo heteroaromático de 5 ó 6 miembros o un sistema anular heteroaromático de 7 a 11 miembros, cada anillo o sistema anular no sustituido o sustituido con 1 a 3 R⁴; o bencilo no sustituido o sustituido con 1 a 3 R⁴; cada R³ᵃ y cada R³ᶜ son independientemente H, halógeno, ciano, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, OR¹² o S(O)ₙR¹¹; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇,cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con por lo menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; cada R³ᵇ y R³ᵈ son, independientemente cada uno, H, halógeno, ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con por lo menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R⁴; R³ᵉ es H, halógeno, ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, OR¹², NR⁹R¹⁰, S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆,alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ o cicloalquenilo C₃₋₆, cada uno no sustituido o sustituido con por lo menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R⁴; R³ᵉ y A pueden tomarse junto con el átomo de carbono al cual están unidos para formar un anillo de 3 a 7 miembros que contiene miembros anulares seleccionados de átomos de carbono y hasta 2 heteroátomos independientemente seleccionados de un átomo de oxígeno, un átomo de azufre, y hasta 2 átomos de nitrógeno, en donde hasta 2 miembros anulares de los átomos de carbono son independientemente seleccionados C(=O) y C(=S) y el miembro anular del átomo de azufre se selecciona de S, S(O) o S(O)₂, el anillo es insustituido o sustituido con hasta 4 sustituyentes independientemente seleccionados del grupo que consiste en halógeno, ciano, y alquilo C₁₋₄; o cuando dos cualquiera de R²ᵃ, R²ᵇ, R²ᶜ, R²ᵈ, R³ᵃ, R³ᵇ, R³ᶜ, R³ᵈ o R³ᵉ son independientemente alquilo C₁₋₄, entonces los dos R²ᵃ, R²ᵇ, R²ᶜ, R²ᵈ, R³ᵃ, R³ᵇ, R³ᶜ, R³ᵈ o R³ᵉ pueden tomarse juntos para formar un anillo; cada R⁴ es independientemente halógeno, ciano, nitro, C(X)R⁵, C(O)OR⁶, C(X)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(O)ₙR¹¹ o SO₂NR⁹R¹⁰; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; cada R⁵ es independientemente H; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R⁵ᵃ es independientemente alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R⁶ es independientemente alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R⁶ᵃ es independientemente alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R⁷ y cada R⁸ son independientemente H; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R⁷ᵃ y R⁸ᵃ es independientemente H, alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R⁹ y cada R¹⁰ son independientemente H, C(X)R⁵, C(O)OR⁶ o C(X)NR⁷R⁸; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R⁹ᵃ y R¹⁰ᵃ es independientemente H, C(X)R⁵ᵃ, C(O)OR⁶ᵃ, C(X)NR⁷ᵃR⁸ᵃ, alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R¹¹ es independientemente alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6 miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R¹¹ᵃ es independientemente alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R¹² es independientemente H; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; o fenilo o un anillo heteroaromático de 5 ó 6miembros, cada anillo no sustituido o sustituido con 1 a 3 R¹³; cada R¹²ᵃ es independientemente alquilo C₁₋₄ o haloalquilo C₁₋₄; cada R¹³ es independientemente halógeno, ciano, nitro, C(X)R⁵ᵃ, C(O)OR⁶ᵃ, C(X)NR⁷ᵃR⁸ᵃ, NR⁹ᵃR¹⁰ᵃ, OR¹²ᵃ, S(O)ₙR¹¹ᵃ o SO₂NR⁹ᵃR¹⁰ᵃ; o alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇ o cicloalquilalquilo C₄₋₈, cada uno no sustituido o sustituido con al menos un sustituyente independientemente seleccionado del grupo que consiste en halógeno, ciano, nitro, OR¹²ᵃ, alquilo C₁₋₄, haloalquilo C₁₋₄ y S(O)ₙR¹¹ᵃ; cada R¹⁴ es independientemente alquilo C₁₋₄; cada X es independientemente O ó S; y cada n es, independientemente, 0, 1 ó 2.
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