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AR109346A1 - Derivados de heterociclos bicíclicos condensados como pesticidas - Google Patents

Derivados de heterociclos bicíclicos condensados como pesticidas

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Publication number
AR109346A1
AR109346A1 ARP170102275A ARP170102275A AR109346A1 AR 109346 A1 AR109346 A1 AR 109346A1 AR P170102275 A ARP170102275 A AR P170102275A AR P170102275 A ARP170102275 A AR P170102275A AR 109346 A1 AR109346 A1 AR 109346A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
cycloalkyl
aminocarbonyl
alkylsulfinyl
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Application number
ARP170102275A
Other languages
English (en)
Inventor
Anthony Millet
Anton Lishchynskyi
Simon Anthony Herbert
Matthieu Willot
Laura Hoffmeister
Dominik Hager
Nina Kausch-Busies
Rdiger Fischer
Marc Mosrin
Andreas Turberg
David Wilcke
Kerstin Ilg
Ulrich Grgens
Original Assignee
Bayer Cropscience Ag
Bayer Ag
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Application filed by Bayer Cropscience Ag, Bayer Ag filed Critical Bayer Cropscience Ag
Publication of AR109346A1 publication Critical patent/AR109346A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La presente solicitud se refiere a compuestos útiles como acaricidas y/o insecticidas para el control de plagas animales y procedimientos e intermedios para su preparación. Reivindicación 1: Los compuestos de la fórmula (1), en la que Aᵃ es -N(R⁷)-, -S(O)ₘ-, -O-, -C(R⁸)(R⁹)- o carbonilo; Aᵇ es -N(R⁷)-, -S(O)ₘ-, -O-, -C(R¹⁰)(R¹¹)- o carbonilo; Aᶜ es -N(R⁷)-, -S(O)ₘ-, -O-, -C(R¹²)(R¹³)- o carbonilo; Aᵈ es -N(R⁷)-, -S(O)ₘ-, -O-, -C(R¹⁴)(R¹⁵)- o carbonilo, en el que como máximo dos de los sustituyentes Aᵃ, Aᵇ, Aᶜ y Aᵈ pueden ser simultáneamente -N(R⁷)-, -O- o -S(O)ₘ-; R¹ es C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ cianoalquilo, C₁₋₆ hidroxialquilo, C₁₋₆ alcoxi-C₁₋₆ alquilo, C₁₋₆ haloalcoxi-C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ alqueniloxi-C₁₋₆ alquilo, C₂₋₆ haloalqueniloxi-C₁₋₆ alquilo, C₂₋₆ haloalquenilo, C₂₋₆ cianoalquenilo, C₂₋₆ alquinilo, C₂₋₆ alquiniloxi-C₁₋₆ alquilo, C₂₋₆ haloalquiniloxi-C₁₋₆ alquilo, C₂₋₆ haloalquinilo, C₂₋₆ cianoalquinilo, C₃₋₈ cicloalquilo, C₃₋₈ cicloalquilo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo-C₃₋₈ cicloalquilo, halo-C₃₋₈ cicloalquilo, amino, C₁₋₆ alquilamino, di-C₁₋₆ alquilo-amino, C₃₋₈ cicloalquilamino, C₁₋₆ alquilcarbonil-amino, C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ haloalquiltio-C₁₋₆ alquilo, C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ haloalquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ haloalquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ alquilcarbonilo-C₁₋₆ alquilo, C₁₋₆ haloalquilcarbonilo-C₁₋₆ alquilo, C₁₋₆ alcoxicarbonilo-C₁₋₆ alquilo, C₁₋₆ haloalcoxicarbonilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilamino, aminosulfonilo-C₁₋₆ alquilo, C₁₋₆ alquilaminosulfonilo-C₁₋₆ alquilo, di-C₁₋₆ alquilo-aminosulfonilo-C₁₋₆ alquilo, o C₁₋₆ alquilo, C₁₋₆ alcoxi, C₂₋₆ alquenilo, C₂₋₆ alquinilo, C₃₋₈ cicloalquilo cada uno opcionalmente mono- o polisustituido de manera idéntica o diferente con arilo, hetarilo o heterociclilo, donde arilo, hetarilo o heterociclilo puede estar cada uno opcionalmente mono- o polisustituido de manera idéntica o diferente con halógeno, ciano, nitro, hidroxi, amino, carboxi, carbamoil, aminosulfonilo, C₁₋₆ alquilo, C₃₋₆ cicloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalquilo, C₁₋₆ haloalcoxi, C₁₋₆ alquiltio, C₁₋₆ alquilsulfinilo, C₁₋₆ alquilsulfonilo, C₁₋₆ alquilsulfimino, C₁₋₆ alquilsulfimino-C₁₋₆ alquilo, C₁₋₆ alquilsulfimino-C₂₋₆ alquilcarbonilo, C₁₋₆ alquilsulfoximino, C₁₋₆ alquilsulfoximino-C₁₋₆ alquilo, C₁₋₆ alquilsulfoximino-C₁₋₆ alquilcarbonilo, C₁₋₆ alcoxicarbonilo, C₁₋₆ alquilcarbonilo, C₃₋₆ trialquilsililo o bencilo, o R¹ es arilo, hetarilo o heterociclilo cada uno opcionalmente mono- o polisustituido de manera idéntica o diferente con halógeno, ciano, nitro, hidroxi, amino, carboxi, carbamoil, C₁₋₆ alquilo, C₃₋₈ cicloalquilo, C₁₋₆ alcoxi, C₁₋₆ haloalquilo, C₁₋₆ haloalcoxi, C₁₋₆ alquiltio, C₁₋₆ alquilsulfinilo, C₁₋₆ alquilsulfonilo, C₁₋₆ alquilsulfimino, C₁₋₆ alquilsulfimino-C₁₋₆ alquilo, C₁₋₆ alquilsulfimino-C₂₋₆ alquilcarbonilo, C₁₋₆ alquilsulfoximino, C₁₋₆ alquilsulfoximino-C₁₋₆ alquilo, C₁₋₆ alquilsulfoximino-C₂₋₆ alquilcarbonilo, C₁₋₆ alcoxicarbonilo, C₁₋₆ alquilcarbonilo, C₃₋₆ trialquilsililo, (=O) (en el caso de heterociclilo solamente) o (=O)₂ (en el caso de heterociclilo solamente); R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ son en forma independiente hidrógeno, ciano, halógeno, nitro, acetilo, hidroxi, amino, SCN, tri-C₁₋₆ alquilsililo, C₃₋₈ cicloalquilo, C₃₋₈ cicloalquilo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo-C₃₋₈ cicloalquilo, halo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ cianoalquilo, C₁₋₆ hidroxialquilo, hidroxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ haloalquenilo, C₂₋₆ cianoalquenilo, C₂₋₆ alquinilo, C₂₋₆ haloalquinilo, C₂₋₆ cianoalquinilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ cianoalcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxi-C₁₋₆ alcoxi, C₁₋₆ alquilhidroxiimino, C₁₋₆ alcoxiimino, C₁₋₆ alquilo-C₁₋₆ alcoxiimino, C₁₋₆ haloalquilo-C₁₋₆ alcoxiimino, C₁₋₆ alquiltio, C₁₋₆ haloalquiltio, C₁₋₆ alcoxi-C₁₋₆ alquiltio, C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ alquilsulfinilo, C₁₋₆ haloalquilsulfinilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfinilo, C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilo, C₁₋₆ haloalquilsulfonilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfonilo, C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfoniloxi, C₁₋₆ alquilcarbonilo, C₁₋₆ alquiltiocarbonilo, C₁₋₆ haloalquilcarbonilo, C₁₋₆ alquilcarboniloxi, C₁₋₆ alcoxicarbonilo, C₁₋₆ haloalcoxicarbonilo, aminocarbonilo, C₁₋₆ alquilo-aminocarbonilo, C₁₋₆ alquilo-aminotiocarbonilo, di-C₁₋₆ alquilo-aminocarbonilo, di-C₁₋₆ alquilo-aminotiocarbonilo, C₂₋₆ alquenil-aminocarbonilo, di-C₂₋₆ alquenil-aminocarbonilo, C₃₋₈ cicloalquil-aminocarbonilo, C₁₋₆ alquilsulfonilamino, C₁₋₆ alquilamino, di-C₁₋₆ alquilamino, aminosulfonilo, C₁₋₆ alquilaminosulfonilo, di-C₁₋₆ alquilo-aminosulfonilo, C₁₋₆ alquilsulfoximino, aminotiocarbonilo, C₁₋₆ alquilo-aminotiocarbonilo, di-C₁₋₆ alquilo-aminotiocarbonilo, C₃₋₈ cicloalquilamino, NHCO-C₁₋₆ alquilo-(C₁₋₆ alquilcarbonilamino), es arilo o hetarilo cada uno opcionalmente mono- o polisustituido de manera idéntica o diferente, en la que (en el caso de hetarilo) opcionalmente puede incluirse al menos un grupo carbonilo y/o donde se consideran como sustituyentes en cada caso: ciano, carboxilo, halógeno, nitro, acetilo, hidroxi, amino, SCN, tri-C₁₋₆ alquilsililo, C₃₋₈ cicloalquilo, C₃₋₈ cicloalquilo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo-C₃₋₈ cicloalquilo, halo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ cianoalquilo, C₁₋₆ hidroxialquilo, hidroxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ haloalquenilo, C₂₋₆ cianoalquenilo, C₂₋₆ alquinilo, C₂₋₆ haloalquinilo, C₂₋₆ cianoalquinilo, C₂₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ cianoalcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxi-C₁₋₆ alcoxi, C₁₋₆ alquilhidroxiimino, C₁₋₆ alcoxiimino, C₁₋₆ alquilo-C₁₋₆ alcoxiimino, C₁₋₆ haloalquilo-C₁₋₆ alcoxiimino, C₁₋₆ alquiltio, C₁₋₆ haloalquiltio, C₁₋₆ alcoxi-C₁₋₆ alquiltio, C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ alquilsulfinilo, C₁₋₆ haloalquilsulfinilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfinilo, C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilo, C₁₋₆ haloalquilsulfonilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfonilo, C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfoniloxi, C₁₋₆ alquilcarbonilo, C₁₋₆ haloalquilcarbonilo, C₁₋₆ alquilcarboniloxi, C₁₋₆ alcoxicarbonilo, C₁₋₆ haloalcoxicarbonilo, aminocarbonilo, C₁₋₆ alquilaminocarbonilo, di-C₁₋₆ alquilo-aminocarbonilo, C₂₋₆ alquenil-aminocarbonilo, di- C₂₋₆ alquenil-aminocarbonilo, C₃₋₈ cicloalquil-aminocarbonilo, C₁₋₆ alquilsulfonilamino, C₁₋₆ alquilamino, di-C₁₋₆ alquilamino, aminosulfonilo, C₁₋₆ alquilaminosulfonilo, di-C₁₋₆ alquilaminosulfonilo, C₁₋₆ alquilsulfoximino, aminotiocarbonilo, C₁₋₆ alquilo-aminotiocarbonilo, di-C₁₋₆ alquilo-aminotiocarbonilo, C₃₋₈ cicloalquilamino, C₁₋₆ alquilcarbonilamino; R⁷ es hidrógeno, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ cianoalquilo, C₁₋₆ hidroxialquilo, C₁₋₆ alcoxi-C₁₋₆ alquilo, C₁₋₆ haloalcoxi-C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ alqueniloxi-C₁₋₆ alquilo, C₂₋₆ haloalqueniloxi-C₁₋₆ alquilo, C₂₋₆ haloalquenilo, C₂₋₆ cianoalquenilo, C₂₋₆ alquinilo, C₂₋₆ alquiniloxi-C₁₋₆ alquilo, C₂₋₆ haloalquinilo, C₃₋₈ cicloalquilo, C₃₋₈ cicloalquilo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo-C₃₋₈ cicloalquilo, halo-C₃₋₈ cicloalquilo, C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo o C₁₋₆ alquilcarbonilo-C₁₋₆ alquilo; Q es un sistema de anillos bicíclico o tricíclico fusionado de 8, 9, 10, 11 ó 12 miembros heterocíclico o heteroaromático saturado o parcialmente saturado, donde al menos un grupo carbonilo puede estar presente opcionalmente y/o donde el sistema de anillos puede estar opcionalmente mono- o polisustituido de manera idéntica o diferente, y donde los sustituyentes se pueden seleccionar de manera independiente entre ciano, halógeno, nitro, acetilo, hidroxi, amino, SCN, tri-C₁₋₆ alquilsililo, C₃₋₈ cicloalquilo, C₃₋₈ cicloalquilo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo-C₃₋₈ cicloalquilo, halo-C₃₋₈ cicloalquilo, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ cianoalquilo, C₁₋₆ hidroxialquilo, hidroxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alquilo, C₁₋₆ alcoxi-C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ haloalquenilo, C₂₋₆ cianoalquenilo, C₂₋₆ alquinilo, C₂₋₆ alquiniloxi-C₁₋₄ alquilo, C₂₋₆ haloalquinilo, C₂₋₆ cianoalquinilo, C₁₋₆ alcoxi, C₁₋₆ haloalcoxi, C₁₋₆ haloalcoxi-C₁₋₆ alquilo, C₂₋₆ alqueniloxi-C₁₋₆ alquilo, C₂₋₆ haloalqueniloxi-C₁₋₆ alquilo, C₁₋₆ cianoalcoxi, C₁₋₆ alcoxicarbonilo-C₁₋₆ alcoxi, C₁₋₆ alcoxi-C₁₋₆ alcoxi, C₁₋₆ alquilhidroxiimino, C₁₋₆ alcoxiimino, C₁₋₆ alquilo-C₁₋₆ alcoxiimino, C₁₋₆ haloalquilo-C₁₋₆ alcoxiimino, C₁₋₆ alquiltio, C₁₋₆ haloalquiltio, C₁₋₆ alcoxi-C₁₋₆ alquiltio, C₁₋₆ alquiltio-C₁₋₆ alquilo, C₁₋₆ alquilsulfinilo, C₁₋₆ haloalquilsulfinilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfinilo, C₁₋₆ alquilsulfinilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfonilo, C₁₋₆ haloalquilsulfonilo, C₁₋₆ alcoxi-C₁₋₆ alquilsulfonilo, C₁₋₆ alquilsulfonilo-C₁₋₆ alquilo, C₁₋₆ alquilsulfoniloxi, C₁₋₆ alquilcarbonilo, C₁₋₆ alquilcarbonilo-C₁₋₆ alquilo, C₁₋₆ alquiltiocarbonilo, C₁₋₆ haloalquilcarbonilo, C₁₋₆ alquilcarboniloxi, C₁₋₆ alcoxicarbonilo, C₁₋₆ haloalcoxicarbonilo, aminocarbonilo, C₁₋₆ alquilo-aminocarbonilo, C₁₋₆ alquilo-aminotiocarbonilo, di-C₁₋₆ alquilo-aminocarbonilo, di-C₁₋₆ alquilo-aminotiocarbonilo, C₂₋₆ alquenil-aminocarbonilo, di-C₂₋₆ alquenil-aminocarbonilo, C₃₋₈ cicloalquil-aminocarbonilo, C₁₋₆ alquilsulfonilamino, C₁₋₆ alquilamino, di-C₁₋₆ alquilamino, aminosulfonilo, C₁₋₆ alquilaminosulfonilo, di-C₁₋₆ alquilo-aminosulfonilo, C₁₋₆ alquilsulfoximino, aminotiocarbonilo, C₁₋₆ alquilo-aminotiocarbonilo, di-C₁₋₆ alquilo-aminotiocarbonilo, C₃₋₈ cicloalquilamino, NHCO-C₁₋₆ alquilo-(C₁₋₆ alquilcarbonilamino), o donde los sustituyentes se pueden seleccionar de manera independiente entre fenilo o un anillo heteroaromático de 5 ó 6 miembros, donde el fenilo o el anillo puede estar opcionalmente mono- o polisustituido de manera idéntica o diferente con C₁₋₆ alquilo, C₂₋₆ alquenilo, C₂₋₆ alquinilo, C₃₋₆ cicloalquilo, C₁₋₆ haloalquilo, C₂₋₆ haloalquenilo, C₂₋₆ haloalquinilo, C₃₋₆ halocicloalquilo, halógeno, CN, NO₂, C₁₋₄ alcoxi, C₁₋₄ haloalcoxi; m es 0, 1 ó 2; n es 0, 1 ó 2.
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