AR120330A1 - Compuesto de piperidinamina que contiene un anillo pirimidina fusionado y preparación, método y uso del mismo - Google Patents

Compuesto de piperidinamina que contiene un anillo pirimidina fusionado y preparación, método y uso del mismo

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AR120330A1
AR120330A1 ARP200102987A ARP200102987A AR120330A1 AR 120330 A1 AR120330 A1 AR 120330A1 AR P200102987 A ARP200102987 A AR P200102987A AR P200102987 A ARP200102987 A AR P200102987A AR 120330 A1 AR120330 A1 AR 120330A1
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Argentina
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alkyl
halogenated
alkoxy
piperidin
amine
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ARP200102987A
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English (en)
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Aiying Guan
Changling Liu
Jinlong Yang
Xiaoxi Fan
Pengfei Zhang
Junfeng Wang
Meng Yang
Xiuhui Chang
Huichao Li
Zhonggang Shan
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Shenyang Sinochem Agrochemicals R & D Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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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
    • A—HUMAN NECESSITIES
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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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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D401/14—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 three or more hetero rings
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract

Un compuesto piperidinamina que contiene un anillo pirimidina fusionado. La estructura se muestra en la fórmula (1). La definición de cada sustituyente de la fórmula se describe en la memoria descriptiva. El compuesto de la presente tiene actividad fungicida de amplio espectro, y presenta efectos de control excelentes del mildiú pulverulento de pepino, mildiú pulverulento de trigo, roya de maíz y ántrax de pepino. El compuesto de la presente también tiene una buena actividad insecticida y acaricida, y presente efectos de control excelentes del Plutella xylostella, oruga militar y Tetranychus cinnabarinus. Reivindicación 1: Un compuesto piperidinamina que contiene pirimidina de anillo fusionado, caracterizado porque el compuesto piperidinamina que contiene pirimidina es un compuesto mostrado en la fórmula (1); R¹ y R² y un anillo pirimidina conectado forman un anillo insaturado de cinco miembros, de seis miembros, de siete miembros o de ocho miembros que contiene C, N, O ó S, que además está sustituido con m R⁴; m se selecciona entre un entero de 0 a 4; cuando m es 0, el anillo no está sustituido; cuando m es mayor a 1, R⁴ pueden ser iguales o diferentes; R⁴ se selecciona entre halógeno, ciano, nitro, C₁₋₁₂ alquilo, C₁₋₁₂ alquilo halogenado, C₁₋₁₂ alcoxi, C₁₋₁₂ alcoxilo halogenado, C₃₋₁₂ cicloalquilo, C₁₋₁₂ alquilamino, C₁₋₁₂ alquilamino halogenado, di(C₁₋₁₂ alquil)amino, di(C₁₋₁₂ alquil)amino halogenado, C₁₋₁₂ alquiltio, C₁₋₁₂ alquiltio halogenado, C₂₋₁₂ alquenilo, C₂₋₁₂ alquinilo, C₂₋₁₂ alqueniloxi, C₂₋₁₂ alqueniloxi halogenado, C₂₋₁₂ alquiniloxi, C₂₋₁₂ alquiniloxi halogenado, C₁₋₁₂ alquilsulfonilo halogenado, C₁₋₁₂ alquilcarbonilo, C₁₋₁₂ alquilcarbonilo halogenado, C₁₋₁₂ alcoxicarbonilo halogenado, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alcoxicarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alcoxicarboniloC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquiltiocarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alquiltiocarboniloC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquilcarboniloxi, C₁₋₁₂ alquilcarboniloxi halogenado, C₁₋₁₂ alcoxicarboniloxi, C₁₋₁₂ alcoxicarboniloxi halogenado, C₁₋₁₂ alquilsulfoniloxi, C₁₋₁₂ alquilsulfoniloxi halogenado, C₁₋₁₂ alcoxi C₁₋₁₂alcoxi o C₁₋₁₂ alcoxiC₁₋₁₂ alcoxi halogenado, carboxiloC₁₋₁₂ alquilo o 1-pirrolidinilo C₁₋₁₂ alquilo; W se selecciona entre hidrógeno, halógeno, amino, C₁₋₁₂ alquilo, C₁₋₁₂ alquilo halogenado, C₃₋₈ cicloalquilo, C₁₋₁₂ alcoxi, C₁₋₁₂ alquiltio, C₁₋₁₂ alquilsulfonilo, C₁₋₁₂ alcoxicarbonilo, 4-morfolinilo C₁₋₁₂ alquilo o 2,6-bis(C₁₋₁₂ alquil)-4-morfolinilo; R³ se selecciona entre hidrógeno, hidroxi, formilo, C₁₋₁₂ alquilo, C₁₋₁₂ alquilo halogenado, C₁₋₁₂ alcoxi, C₁₋₁₂ alcoxi halogenado, C₃₋₁₂ cicloalquilo, C₁₋₁₂ alquiltio, C₂₋₁₂ alqueniltio, C₂₋₁₂ alquenilo, C₂₋₁₂ alquinilo, C₂₋₁₂ alquenilo halogenado, C₂₋₁₂ alquinilo halogenado, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquilsulfinilo, C₁₋₁₂ alquilsulfinilo halogenado, C₁₋₁₂ alquilsulfonilo, C₁₋₁₂ alquilsulfonilo halogenado, C₁₋₁₂ alquilaminosulfonilo, di(C₁₋₁₂ alquil)aminosulfonilo, C₁₋₁₂ alquilsulfonilaminocarbonilo, C₁₋₁₂ alquilcarbonilaminosulfonilo, C₃₋₁₂ cicloalquiloxicarbonilo, C₁₋₁₂ alquilcarbonilo, C₁₋₁₂ alquilcarbonilo halogenado, C₁₋₁₂ alcoxicarbonilo, C₁₋₁₂ alcoxicarbonilo halogenado, C₁₋₁₂ alquilcarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alcoxicarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alquilaminocarbonilo, di(C₁₋₁₂ alquil)aminocarbonilo, C₂₋₁₂ alqueniloxicarbonilo, C₂₋₁₂ alquiniloxicarbonilo, C₁₋₁₂ alcoxiC₁₋₁₂ alcoxicarbonilo, C₁₋₁₂ alquilaminotio, di(C₁₋₁₂ alquil)aminotio, y arilcarboniloC₁₋₆ alquilo, arilcarbonilo, ariloxicarbonilo, ariloC₁₋₆ alquiloxicarbonilo, ariloC₁₋₆ alquilo, heteroarilcarboniloC₁₋₆ alquilo, heteroarilcarbonilo, heteroariloxicarbonilo, heteroariloC₁₋₆ alquiloxicarbonilo o heteroariloC₁₋₆ alquilo no sustituido o sustituido adicionalmente con 1 - 5 de los siguientes grupos: halógeno, nitro, ciano, C₁₋₆ alquilo, C₁₋₆ alquilo halogenado, C₁₋₆ alcoxi o C₁₋₆ alcoxi halogenado; Q se selecciona entre anillo benceno, piridina, pirimidina, anillo piridazina, anillo pirazina, s-triazina, anillo unsym-triazina, anillo fusionado o heterociclo fusionado, donde estos anillos no están sustituidos o están sustituidos con n R; R se selecciona entre halógeno, amino, ciano, nitro, formilo, C₁₋₁₂ alquilo, C₁₋₁₂ alquilo halogenado, C₁₋₁₂ alcoxi, C₁₋₁₂ alcoxi halogenado, C₃₋₁₂ cicloalquilo, C₁₋₁₂ alquilamino, C₁₋₁₂ alquilamino halogenado, di(C₁₋₁₂ alquil)amino, di(C₁₋₁₂ alquil)amino halogenado, C(=O)NR⁵R⁶, C₁₋₁₂ alquiltio, C₁₋₁₂ alquiltio halogenado, C₂₋₁₂ alquenilo, C₂₋₁₂ alquinilo, C₂₋₁₂ alqueniloxi, C₂₋₁₂ alqueniloxi halogenado, C₂₋₁₂ alquiniloxi, C₂₋₁₂ alquiniloxi halogenado, C₁₋₁₂ alquilsulfonilo, halógeno C₁₋₁₂ alquilsulfonilo, C₁₋₁₂ alquilcarbonilo, C₁₋₁₂ alquilcarbonilo halogenado, C₁₋₁₂ alcoxicarbonilo, C₁₋₁₂ alcoxicarbonilo halogenado, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo, C₁₋₁₂ alcoxiC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo, C₁₋₁₂ alquiltioC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alcoxicarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alcoxicarboniloC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquiltiocarboniloC₁₋₁₂ alquilo, C₁₋₁₂ alquiltiocarboniloC₁₋₁₂ alquilo halogenado, C₁₋₁₂ alquilcarboniloxi, C₁₋₁₂ alquilcarboniloxi halogenado, C₁₋₁₂ alcoxicarboniloxi, C₁₋₁₂ alcoxicarboniloxi halogenado, C₁₋₁₂ alquilsulfoniloxi, C₁₋₁₂ alquilsulfoniloxi halogenado, C₁₋₁₂ alcoxi C₁₋₁₂ alcoxi o C₁₋₁₂ alcoxi C₁₋₁₂ alcoxi halogenado; R⁵ y R⁶ pueden ser iguales o diferentes, y se seleccionan respectivamente entre hidrógeno, C₁₋₁₂ alquilo o C₁₋₁₂ alquilo halogenado; n se selecciona entre un entero de 0 a 4; cuando n es 0, el anillo no está sustituido; cuando n es mayor a 1, R pueden ser iguales o diferentes; cuando Q se selecciona entre fenilo no sustituido o sustituido, los siguientes compuestos no están incluidos: N-(1-(p-tolil)piperidin-4-il)quinazolin-4-amina, 7-cloro-N-(1-(4-metoxifenil)piperidin-4-il)quinazolin-4-amina, 6-bromo-N-(1-(4-metoxifenil)piperidin-4-il)quinazolin-4-amina, N-(1-(4-fluorofenil)piperidin-4-il)quinazolin-4-amina, N-(1-(4-butilfenil)piperidin-4-il)quinazolin-4-amina, N-(1-(4-(tert-butil)fenil)piperidin-4-il)quinazolin-4-amina, N-(1-(4-ciclohexilfenil)piperidin-4-il)quinazolin-4-amina; cuando Q se selecciona entre piridilo no sustituido o sustituido, los siguientes compuestos no están incluidos: 7-cloro-N-(1-(6-metilpiridin-2-il)piperidin-4-il)quinazolin-4-amina y 7-cloro-N-(1-(piridin-2-il)piperidin-4-il)quinazolin-4-amina; cuando Q se selecciona entre pirimidinilo no sustituido o sustituido, los siguientes compuestos no están incluidos: 5-fluoro-N-(1-(pirimidin-2-il)piperidin-4-il)quinazolin4-amina y 6-fluoro-N-(1-(pirimidin-2-il)piperidin-4-il)quinazolin-4-amina; cuando Q se selecciona entre piridazinilo no sustituido o sustituido, el siguiente compuesto no está incluido: 6-fluoro-N-(1-(piridazin-3-il)piperidin-4-il)quinazolin-4-amina; cuando Q se selecciona entre 3-piridazinilo no sustituido, R³ no es metilo; Q no se selecciona entre 4-pirimidinilo sustituido con 5-hidrógeno; cuando R¹ y R² y el anillo pirimidina conectado forman un anillo 6-cloropirido[3,2-d]pirimidina, Q no es 3-piridazinilo, 2-pirazinilo, 6-metil-3-piridilo, 3-piridilo, 2-piridilo o 2-pirimidinilo; cuando R¹ y R² y el anillo pirimidina conectado forman un anillo pirimidopirrol, Q no es fenilo no sustituido, fenilo sustituido con C₁₋₁₂ alquilsulfonilo o 3-piridazinilo; cuando R¹ y R² y el anillo pirimidina conectado forman un anillo pirimidotiofeno, Q no es fenilo no sustituido, 2-pirimidinilo, 2-pirazinilo, 3-piridazinilo; los siguientes dos compuestos no están incluidos: 6-etil-N-(1-(4-fluorofenil)piperidin-4-il)tieno[2,3-d]pirimidin-4-amina y 6-etil-N-(1-(5-(trifluorometil)piridin-2-il)piperidin-4-il)tieno[2,3- d]pirimidin-4-amina; cuando R¹ y R² y el anillo pirimidina conectado forman un anillo pirimidolopirazol, Q no es 2-pirimidinilo no sustituido, 3-metoxifenilo, 4-metoxifenilo, 6-cloropiridazin-3- ilo; cuando R¹ y R² y el anillo pirimidina conectado forman un anillo pirimidoimidazol, Q no es 2-metoxifenilo, 4-metoxifenilo, 2-piridilo, 5-metilpiridin-2-ilo o 6-metilpiridin-2-ilo.
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