AR111498A1 - Compuestos heterocíclicos como agentes plaguicidas - Google Patents

Compuestos heterocíclicos como agentes plaguicidas

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Publication number
AR111498A1
AR111498A1 ARP180101174A ARP180101174A AR111498A1 AR 111498 A1 AR111498 A1 AR 111498A1 AR P180101174 A ARP180101174 A AR P180101174A AR P180101174 A ARP180101174 A AR P180101174A AR 111498 A1 AR111498 A1 AR 111498A1
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Argentina
Prior art keywords
alkyl
cycloalkyl
halogen
alkoxy
alkylamino
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ARP180101174A
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English (en)
Inventor
Turberg Andreas Dr
Portz Daniela Dr
Ulrich Grgens
Horn Karin Dr
Vermeer Arnoldus Dr
Horstmann Sebastian Dr
Ilg Kerstin Dr
Bhnke Niels Dr
Arlt Alexander Dr
Velten Robert Dr
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Bayer Cropscience Ag
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Publication of AR111498A1 publication Critical patent/AR111498A1/es

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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
    • C07D213/04—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
    • C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • 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
    • A01N43/34—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
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    • A01P7/00—Arthropodicides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01P7/00—Arthropodicides
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • 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
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    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • General Health & Medical Sciences (AREA)
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  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
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  • Agronomy & Crop Science (AREA)
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  • Insects & Arthropods (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)

Abstract

Procedimientos e intermediarios para su preparación y a su uso para combatir plagas animales, en particular para combatir insectos. Reivindicación 1: Compuestos de la fórmula (1), en la que Z representa naftilo, dibenzo[b,d]furanoilo, dibenzo[b,d]tiofenilo, carbazolilo, indanilo, benzotiofenilo, benzofuranoilo, indolilo, fluoroenilo, fenantrenilo, antracenilo eventualmente sustituido o representa un fenilo de la fórmula estructural (2), y el fenilo sustituido de la fórmula estructural (2) que puede portar hasta dos otros sustituyentes seleccionados del grupo de halógeno, ciano, alquilo C₁₋₄, halógenoalquilo C₁₋₄, alcoxi C₁₋₄, halógenoalcoxi C₁₋₄, alquilsulfanilo C₁₋₄, cicloalquilo C₃₋₆ o halógenocicloalquilo C₃₋₆; Y representa O, S, -CH₂, -NR⁵; A¹ representa N o -CR¹; A² representa N o -CR²; A³ representa N o -CR³; A⁴ representa N o -CR⁴; allí al menos uno y como máximo dos de los átomos A¹, A², A³ o A⁴ en el anillo aromático representa N; X representa oxígeno, sulfanilo, sulfinilo, sulfonilo, -CH₂, carbonilo, -CHOH o -NR⁶; R¹, R², R³ y R⁴ cada uno independientemente entre sí representa hidrógeno, halógeno, nitro, ciano, aminocarbonilo, aminosulfonilo, y alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄, alqueniloxi C₂₋₄, alquiniloxi C₂₋₄, cicloalcoxi C₃₋₆, N-mono-alquilamino C₁₋₄, N-mono-cicloalquilamino C₃₋₆, N,N-di-alquilamino C₁₋₄, N,N-di-cicloalquilamino C₃₋₆, N,N-cicloalquil C₃₋₆-alquilamino C₁₋₄, N-alcanoilamino C₁₋₄, N-cicloalcanoilamino C₃₋₆, N-alcanoil C₁₋₄-N-alquilamino C₁₋₄, N-cicloalcanoil C₃₋₆-N-alquilamino C₁₋₄, N-cicloalcanoil C₃₋₆-N-cicloalquilamino C₃₋₆, N-alcanoil C₁₋₄-N-cicloalquilamino C₃₋₆, alcoxicarbonilo C₁₋₄, cicloalcoxicarbonilo C₃₋₆, alcanoilo C₁₋₄, cicloalcanoilo C₃₋₆, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, cicloalquilsulfanilo C₃₋₆, cicloalquilsulfinilo C₃₋₆, cicloalquilsulfonilo C₃₋₆, N-alquilaminocarbonilo C₁₋₄, N-cicloalquilaminocarbonilo C₃₋₆, N,N-di-alquilaminocarbonilo C₁₋₄, N,N-di-cicloalquilaminocarbonilo C₃₋₆, N,N-cicloalquil C₃₋₆-alquilaminocarbonilo C₁₋₄, -CH=N-O-[alquil C₁₋₄], -CH=N-O-[cicloalquilo C₃₋₆], -C[alquil C₁₋₄]=N-O-[alquil C₁₋₄], -C[cicloalquilo C₃₋₆]=N-O-[alquil C₁₋₄], -C[alquil C₁₋₄]=N-O-[cicloalquilo C₃₋₆], -C[cicloalquilo C₃₋₆]=N-O-[cicloalquilo C₃₋₆] cada uno eventualmente sustituido; R⁵ representa hidrógeno o alquilo C₁₋₄, cicloalquilo C₃₋₆, alcanoilo C₁₋₃ dado el caso sustituidos; R⁶ representa hidrógeno o alquilo C₁₋₄, cicloalquilo C₃₋₆, alcanoilo C₁₋₄ dado el caso sustituidos o una conformación de anillo con R⁸ que se forma de 1 a 3 grupos CH₂; R⁷ representa hidrógeno o alquilo C₁₋₄, cicloalquilo C₃₋₆ dado cl caso sustituidos o una conformación de anillo con R⁸ que se forma de 1 a 3 grupos CH₂; R⁸ representa hidrógeno o representa alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, cicloalquilo C₃₋₆ dado el caso sustituidos o junto con R⁶ o R⁷ cierran un anillo que se forma de 1 a 3 grupos CH₂ o junto con R⁹ cierran un anillo heterocíclico de 4 a 6 miembros, el que en el caso de un anillo heterocíclico de 5 a 6 miembros pueda contener otros heteroátomos y dado el caso puede estar mono- o polisustituido, de manera igual o diferente con halógeno, ciano o alquilo C₁₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄ cada uno eventualmente puede estar mono- o polisustituido, de manera igual o diferente con halógeno; R⁹ representa alquilo C₁₋₄, cicloalquilo C₃₋₆, alquenilo C₂₋₄, alquinilo C₂₋₄, N-mono-alquilamino C₁₋₄, N,N-di-alquilamino C₁₋₄, alcoxi C₁₋₄, alqueniloxi C₂₋₄, alquiniloxi C₂₋₄, cicloalcoxi C₃₋₆, alquilcarbonilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, alcoxicarbonilo C₁₋₄ cada uno eventualmente sustituido, para el caso que R⁷ representa hidrógeno o alquilo C₁₋₄, cicloalquilo C₃₋₆ eventualmente sustituido o para el caso que R⁷ con R⁸ forme un anillo de 5 ó 6 miembros, o R⁹ representa alquilo C₁₋₄, cicloalquilo C₃₋₆, alquenilo C₂₋₄, alquinilo C₂₋₄, N-mono-alquilamino C₁₋₄, N,N-di-alquilamino C₁₋₄, alcoxi C₁₋₄, alqueniloxi C₂₋₄, alquiniloxi C₂₋₄, cicloalcoxi C₃₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄ cada uno eventualmente sustituido, para el caso que R⁷ forme un anillo de 4 miembros junto con R⁸ o R⁸ y R⁹ representan una conformación de anillo heterocíclico de 4 a 6 miembros, el que en el caso de un anillo heterocíclico de 5 a 6 miembros pueda contener otros heteroátomos y dado el caso esta mono- o polisustituido, de manera igual o diferente con halógeno, ciano o alquilo C₁₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄, pudiendo cada uno eventualmente estar mono- o polisustituido, de manera igual o diferente con halógeno; R¹⁰ representa halógeno, nitro, ciano, -SF₅ o representa fenilo, pirid-2-ilo, pirid-3-ilo, pirid-4-ilo, tiofen-2-ilo, tiofen-3-ilo, alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄, alqueniloxi C₂₋₄, alquiniloxi C₂₋₄, cicloalcoxi C₃₋₆, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, cicloalquilsulfanilo C₃₋₆, cicloalquilsulfinilo C₃₋₆, cicloalquilsulfonilo C₃₋₆, -CH=N-O-[alquil C₁₋₄], -C[alquil C₁₋₄]=N-O-[alquil C₁₋₄] dado el caso mono- o polisustituido, de manera igual o diferente con halógeno, ciano, nitro, -SF₅, alquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, halógenoalquilo C₁₋₄, halógenoalquenilo C₂₋₄, alcoxi C₁₋₄, halógenoalcoxi C₁₋₄, alqueniloxi C₂₋₄, halógenoalquenil C₂₋₄oxi, alquiniloxi C₂₋₄, cicloalcoxi C₃₋₆, halógenocicloalcoxi C₃₋₆, cicloalquilo C₃₋₆, halógenocicloalquilo C₃₋₆, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, halógenoalquilsulfonilo C₁₋₄, halógenoalquilsulfanilo C₁₋₄, halógenoalquilsulfinilo C₁₋₄, cicloalquilsulfanilo C₃₋₆, cicloalquilsulfinilo C₃₋₆, cicloalquilsulfonilo C₃₋₆, arilo C₆-,C₁₀-,C₁₄, ariloxi C₆-,C₁₀-,C₁₄, bencilo, benciloxi, benciltio, ariltio C₆-,C₁₀-,C₁₄, arilamino C₆-,C₁₀-,C₁₄, bencilamino, heterociclilo, trialquilsililo; R¹¹ representa hidrógeno, halógeno, ciano o nitro o representa alquilo C₁₋₄, cicloalquilo C₃₋₅, alcoxi C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, -CH=N-O-[alquil C₁₋₄], -C[alquil C₁₋₄]=N-O-[alquil C₁₋₄] cada uno eventualmente sustituido; así como sales, complejos metálicos, N-óxidos y formas tautoméricas de los compuestos de la fórmula (1); con la condición que esté excluido el compuesto 1-[4-(6-{2-[3-(clorometil)fenil]etil}piridin-3l-il)piperazin-1-il]etanona.
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