AR094112A1 - (hetero)arilacrilamidas utiles para controlar ectoparasitos - Google Patents

(hetero)arilacrilamidas utiles para controlar ectoparasitos

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Publication number
AR094112A1
AR094112A1 ARP130104851A ARP130104851A AR094112A1 AR 094112 A1 AR094112 A1 AR 094112A1 AR P130104851 A ARP130104851 A AR P130104851A AR P130104851 A ARP130104851 A AR P130104851A AR 094112 A1 AR094112 A1 AR 094112A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
cycloalkyl
mono
haloalkyl
Prior art date
Application number
ARP130104851A
Other languages
English (en)
Inventor
Ogawa Chikako
Tahtaoui Chouaib
Nanchen Steve
Gauvry Nolle
Dupont Emilie
Original Assignee
Novartis Tiergesundheit 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 Novartis Tiergesundheit Ag filed Critical Novartis Tiergesundheit Ag
Publication of AR094112A1 publication Critical patent/AR094112A1/es

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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
    • A—HUMAN NECESSITIES
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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
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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
    • A01N37/30—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 containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • 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
    • 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
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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
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    • A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
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    • C07—ORGANIC CHEMISTRY
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    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
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Abstract

Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), incluyendo todos los isómeros geométricos y estereoisómeros, N-óxidos, S-óxidos, sales y prodrogas del mismo, donde T¹, T² y T³ son en forma independiente entre sí C(R⁰) o es N, donde la cantidad de átomos de nitrógeno en T¹ - T³ es entre 0 y 2; R⁰ es H o R¹; n es 1, 2 ó 3; R¹ es halógeno, ciano (-CN), nitro (-NO₂), alquilo C₁₋₆, cicloalquilo C₃₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, alquil C₁₋₆sulfinilo, haloalquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, haloalquil C₁₋₆sulfonilo, N-mono- o N,N-di-alquil C₁₋₆amino, alcoxi C₁₋₆carbonilo, alquil C₁₋₆carbonilo, aminosulfonilo, alquil C₁₋₆aminosulfonilo, alquil C₁₋₆sulfonilamino o fenilo que no está sustituido o está sustituido con halógeno, ciano, nitro, haloalquilo C₁₋₄, haloalcoxi C₁₋₄ o haloalquil C₁₋₄tio; o R¹ es una cadena carbonada C₁₋₄ que contiene opcionalmente 1 - 2 heteroátomos del grupo de N, S, O, que se une dos posiciones del anillo adyacentes y que forma un anillo alifático, aromático, heteroaromático o heterocíclico que está opcionalmente monosustituido o polisustituido con alquilo C₁₋₆ o halógeno, en cuyo caso n es 2; X es alquilo C₁₋₆, alcoxi C₁₋₄-alquilo C₁₋₆, alcoxi C₁₋₆carbonilo, haloalquilo C₁₋₆, cicloalquilo C₃₋₆ o halocicloalquilo C₃₋₆; R² es hidrógeno, ciano, hidroxilo, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆ o cicloalquilo C₃₋₆; R³ es hidrógeno, alquilo C₁₋₆ o alquil C₁₋₆carbonilo; R⁴ y R⁵ son en forma independiente entre sí hidrógeno, halógeno, alquilo C₁₋₆ o alcoxi C₁₋₆; Y es un radical seleccionado del grupo de fórmulas (2), donde el segundo sitio de conexión (derecha) en cada caso se conecta a la unidad C(O)NR⁷R⁸; m es el entero 0, 1 ó 2; m1 es el entero 0 ó 1; R⁶ es halógeno, ciano, nitro, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alquilciclo-alquilo C₄₋₇, cicloalquilalquilo C₄₋₇, alcoxi C₁₋₆, alquil C₁₋₆carbonilo o alcoxi C₁₋₆carbonilo; A es un anillo heteroaromático de 5 ó 6 miembros anelado que comprende T⁸; T⁴ es S ó O; T⁵ es N, CH o C(CH₃); T⁶ y T⁷ son en forma independiente entre sí CH o N donde la cantidad de átomos de nitrógeno en T⁶ - T⁷ es 0 ó 1; T⁸ es N ó O; R⁷ es H, alquilo C₁₋₆ que no está sustituido o está sustituido con halógeno, alcoxi C₁₋₄, alquil C₁₋₂tio, ciano, nitro, amino o N-mono- o N,N-di-alquil C₁₋₄amino, o es alquenilo C₂₋₄, alquinilo C₂₋₄ o cicloalquilo C₃₋₆; R⁸ es H; un grupo -CH=N-OR⁹; un radical Q; un radical Q¹; o es alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alquilciclo-alquilo C₄₋₇, cicloalquilalquilo C₄₋₇, biciclo-alquileno C₅₋₁₀ o cicloalcanona C₃₋₆ que en cada caso no está sustituido o está sustituido en la unidad alquilo, cicloalquilo, alquenilo o alquinilo con halógeno, hidroxi, carboxi (COOH), alquilo C₁₋₄, alcoxi C₁₋₆, halo-alcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, ciano, nitro, amino, N-mono- o N,N-di-alquil C₁₋₆amino, cicloalquil C₃₋₆amino, alcoxi C₁₋₆carbonilo, alquil C₂₋₆carbonilo, alquil C₁₋₆carbonilamino, aminosulfonilo, N-mono- o N,N-di-alquil C₁₋₄aminosulfonilo, un grupo -C(W)NR⁹R¹⁰ o un radical Q; o R⁷ y R⁸ juntos son un grupo =C(R¹¹)-NR¹²R¹³ o =C(R¹¹)-C(NH₂)-OR¹²); o R⁷ y R⁸ junto con el átomo de N al cual están unidos, forman un anillo de entre 3 y 7 miembros que contiene opcionalmente un heteroátomo adicional seleccionado entre el grupo que consiste en N, S y O, y donde el anillo no está sustituido adicionalmente o está monosustituido o polisustituido con alquilo C₁₋₂, haloalquilo C₁₋₂, alcoxi C₁₋₂, hidroxi, halógeno, ciano, nitro, N,N-di-alquil C₁₋₂aminometilo o N,N-di-alquil C₁₋₂aminocarbonilmetilo; Q y Q son en forma independiente entre sí un arilo C₆₋₁₀, un anillo heterocíclico alifático o aromático de 4, 5, ó 6 miembros, o un anillo heterobicíclico fusionado alifático o aromático de 8, 9 ó 10 miembros, donde cada uno de los mismos no está sustituido o está monosustituido o polisustituido con halógeno, hidroxi, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₂, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, ciano, nitro, amino, N-mono- o N,N-di-alquil C₁₋₆amino, cicloalquil C₃₋₆amino, COOH, alcoxi C₁₋₆-carbonilo, alquil C₂₋₆carbonilo, alquil C₁₋₆carbonilamino, aminocarbonilo, N-mono- o N,N-di-alquil C₁₋₆aminocarbonilo, aminosulfonilo, N-mono- o N,N-di-alquil C₁₋₄aminosulfonilo, fenil-alquilo C₁₋₄ no sustituido o sustituido con halógeno o nitro, heterociclil-alquilo C₁₋₄ de 5 ó 6 miembros o un radical Q; Q es un anillo carbocíclico C₆₋₁₀ o un anillo heterocíclico de 4, 5 ó 6 miembros, donde cada uno de los mismos es aromático o no, donde cada uno de los mismos no está sustituido o está monosustituido o polisustituido con halógeno, hidroxi, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, ciano, nitro, amino, N-mono- o N,N-di-alquil C₁₋₆amino, cicloalquil C₃₋₆amino, COOH, alcoxi C₁₋₆carbonilo, alquil C₂₋₆carbonilo, alquil C₁₋₆carbonilamino, aminocarbonilo, N-mono- o N,N-di-alquil C₁₋₆aminocarbonilo, aminosulfonilo, o N-mono- o N,N-di-alquil C₁₋₄aminosulfonilo; Q¹ es un radical de fórmula (3), donde Z es O ó CH₂ y R¹⁴ es H, alquilo C₁₋₄, o haloalquilo C₁₋₄; R⁹ es H o alquilo C₁₋₆; R¹⁰ es H, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alquilciclo-alquilo C₄₋₇ o cicloalquilalquilo C₄₋₇, que en cada caso no está sustituido o está sustituido en la unidad alquilo, alquenilo, alquinilo o cicloalquilo con halógeno, ciano, nitro, hidroxi, carboxi (COOH), alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, amino, N-mono- o N,N-di-alquil C₁₋₆amino, cicloalquil C₃₋₆amino, alcoxi C₁₋₆carbonilo, alquil C₂₋₆carbonilo, alquil C₁₋₆carbonilamino, aminocarbonilo, N-mono- o N,N-di-alquil C₁₋₆amino-carbonilo, aminosulfonilo, N-mono- o N,N-di-alquil C₁₋₄amino-sulfonilo o un radical Q; R¹¹ es H alquilo C₁₋₆ o alcoxi C₁₋₆; R¹² y R¹³ son en forma independiente entre sí alquilo C₁₋₆; y W y W son en forma independiente entre sí O ó S.
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