AR043064A1 - Piperidinas y piridinas n-(arilmetilo sustituidas)-4-(metilo disustituidas) - Google Patents

Piperidinas y piridinas n-(arilmetilo sustituidas)-4-(metilo disustituidas)

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Publication number
AR043064A1
AR043064A1 ARP030104688A ARP030104688A AR043064A1 AR 043064 A1 AR043064 A1 AR 043064A1 AR P030104688 A ARP030104688 A AR P030104688A AR P030104688 A ARP030104688 A AR P030104688A AR 043064 A1 AR043064 A1 AR 043064A1
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AR
Argentina
Prior art keywords
optionally substituted
substituted
alkyl
formula
nr15c
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ARP030104688A
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English (en)
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Fmc Corp
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Publication of AR043064A1 publication Critical patent/AR043064A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
    • C07D241/52—Oxygen atoms
    • 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
    • A01N43/34—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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/24—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
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    • C07—ORGANIC CHEMISTRY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
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    • C07—ORGANIC CHEMISTRY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
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    • 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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    • 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
    • C07D401/10—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 aromatic rings
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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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    • 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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    • C07D417/12—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 chain containing hetero atoms as chain links
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    • C07D513/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
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  • Plural Heterocyclic Compounds (AREA)
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  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Derivados de piperidina y piridina N-(arilo substituidas)-4-(metilo substituidas) que han suministrado una actividad insecticida inesperada. También se revelan las composiciones que comprenden una cantidad insecticidamente efectiva de por lo menos un compuesto de fórmula (1), y opcionalmente, una cantidad efectiva de por lo menos un segundo compuesto, con por lo menos un portador insecticidamente compatible, juntamente con métodos para controlar insectos que comprenden aplicar dichas composiciones en un lugar donde los insectos están presentes o se espera que se encuentren presentes. Reivindicación 1: Un compuesto de la fórmula (1), donde; m, n, q, r, y s son independientemente seleccionados entre 0 ó 1; y p es 0, 1, 2, ó 3; A es seleccionado entre C y CH, formando un anillo azino de seis miembros a partir de piperidina, 1,4-dihidropiridina, y 1, 2, 5, 6-tetrahidropiridina; R2, R3, R4, R5, y R6 son independientemente seleccionados entre hidrógeno, halógeno, alquilo, haloalquilo, hidroxilo, alcoxi, haloalcoxi, pentahalotio, alquiltio, ciano, nitro, alquilcarbonilo, alcoxicarbonilo, arilo, o ariloxi, siempre que por lo menos uno entre R2, R3, R4, R5, y R6 son distintos de hidrógeno; y donde cualquiera entre R2 y R3, o R3 y R4 se toman conjuntamente con -OCF2O-,-OCF2CF2-, -CF2CF2O-, o -CH=CHCH=CH-, formando un anillo benzo-fusionado; y cuando, (a) m y n son 0; se forma un doble enlace entre carbono de metilo (a) y la posición 4 del anillo azino de seis miembros fórmula (2), donde B es fenilo substituido con R9, R10, R11, R12, y R13 fórmula (3), donde R9, R10, R11, R12, y R13 son independientemente seleccionados entre hidrógeno, halógeno, alquilo, haloalquilo, hidroxilo, alcoxi, haloalcoxi, mercapto, y alquiltio, ciano, alquilcarbonilo, alcoxicarbonilo, o ariloxi; y, donde cualquier R9 y R10, o R10 y R11 pueden tomarse conjuntamente con -OCF2O-, -OCF2CF2-,o -CF2CF2O-, formando un anillo benzo-fusionado, siempre que por lo menos uno de R9, R10, R11, R12 y R13 no es hidrógeno; y cuando (b) m es 1, y n es 0; se forma un doble enlace entre carbono de metilo (a) y la posición 4 del anillo azino de seis miembros fórmula (4), donde B es un grupo de puente desde el carbono de metilo (a) a R; donde B es seleccionado entre O, S, *CH2O, *OCH2, OC(=O)O, *OC(=O)NR15, *NR15C(=O)O, *OC(=S)NR15, *NR15C(=S)O, *OCH2C(=O)NR15, *NR15C(=O)CH2O, *CH2OC(=O)NR15, *NR15C(=O)OCH2, *NR15CH2, *CH2NR15,*NR15C(=O), *C(=O)NR15, *NR15SO2, *SO2NR15, *NR15NHSO2, *SO2NHNR15, *OC(=O)NR15SO2, *SO2NR15C(=O)O, *OC(=O)NR15CHR16, *CHR16NR15C(=O)O, *NR15C(=O)NR16; 1,4-dioxiciclohexilo, o 4-oxipiperidin-1-ilo, donde el asterisco indica la fijación al carbono de metilo (a); donde R15 y R16 son independientemente seleccionados entre hidrógeno, alquilo, alquilaminocarbonilo, y arilcarbonilo donde el arilo es opcionalmente substituido con halógeno, alquilo, alcoxi, haloalquilo, haloalcoxi, o nitro; donde R es alquilo, cicloalquilo, alquenilo, o alcoxicarbonilo; o R es fenilo substituido con R17, R18, R19, R20, y R21 fórmula (5); o R es pirid-2-ilo substituido con R18, R19, R20, y R21 fórmula (6), o pirid-3-ilo substituido con R17, R19, R20 y R21 fórmula (7), o pirid-4-ilo substituido con R17, R18, R20 y R21 fórmula (8), o piridazin-3-ilo substituido con R19, R20 y R21 fórmula (9), donde R17, R18, R19, R20, y R21 son independientemente seleccionados entre hidrógeno, halógeno, alquilo, haloalquilo, alcoxi, haloalcoxi, alquiltio, haloalquiltio, ciano, nitro, alquilcarbonilo, alcoxicarbonilo, alcoxicarbonilamino, arilo, ariloxi, y 2- alquil-2H-tetrazol, y donde cualquiera entre de R17 y R18, o R18 y R19 pueden tomarse conjuntamente con -OCF2O-,-OCF2CF2-, -CF2CF2O-, o -CH=CHCH=CH-, para formar anillos benzo-fusionados; y cuando (c) m y n son 1; se forma un enlace simple entre el carbono de metilo (a) y la posición 4 del anillo azino de seis miembros, fórmula (10), donde B es un grupo de puente desde el carbono de metilo (a) a R; donde B es seleccionado entre O, S, *CH2O, *OCH2, OC(=O)O, *OC(=O)NR15, *NR15C(=O)O, *OC(=S)NR15, *NR15C(=S)O, *OCH2C(=O)NR15, *NR15C(=O)CH2O, *CH2OC(=O)NR15, *NR15C(=O)OCH2, *NR15CH2, *CH2NR15,*NR15C(=O), *C(=O)NR15, *NR15SO2, *SO2NR15, *NR15NHSO2, *SO2NHNR15, *OC(=O)NR15SO2, *SO2NR15C(=O)O, *OC(=O)NR15CHR16, *CHR16NR15C(=O)O, *NR15C(=O)NR16; 1,4-dioxiciclohexilo, o 4-oxipiperidin-1-ilo, donde el asterisco indica la fijación al carbono de metilo (a); donde R15 y R16 se describen anteriormente; y R es alquilo, cicloalquilo, alquenilo, o alcoxicarbonilo; o R es fenilo substituido con R17, R18, R19, R20, y R21; pirid-2-ilo substituido con R18, R19, R20, y R21, o pirid-3-ilo substituido con R17, R19, R20 y R21, o pirid-4-ilo substituido con R17, R18, R20 y R21, o piridazin-3-ilo substituido con R19, R20 y R21, donde R17, R18, R19, R20, y R21, se describen anteriormente; R1 es seleccionado entre hidrógeno, alquilo, alcoxialquilo, o arilo; donde p es 1, 2, o 3; D es -CH2-, y se forma un derivado de azabiciclo del anillo azino de seis miembros; cuando q es 0, y r es 1, se forma un derivado de N-óxido de nitrógeno de anillo azino de seis miembros; cuando q es 1 y r es 0 o 1; R7 es seleccionado entre alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, dialquilaminoalquilo, alquilaminocarboniloxialquilo, alquiltioalquilo, alquilsulfonilalquilo, alquilcarboniloxialquilo, alcoxicarbonilalquilo, carboxialquilo, arilalquilo, arilcarbonilo, sulfonato, o sulfonatoalquilo, y puede llevar una carga negativa que produce una sal interior; y un ión separado es cloruro, bromuro, ioduro, o un sulfonato o sulfato; cuando s es 0 o 1; R8 es seleccionado entre hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo, alcoxi, alcoxialquilo, amino, morfolinilo, indolilo opcionalmente substituido. piperidinilo, (piridil)alquenilo opcionalmente substituido, 1,2, 3,4-tetrahidronaftilenilo opcionalmente substituido, arilpirazolilo opcionalmente substituido, benzo[b]tiofenilo, 5-hidropiridino[1, 2a] pirimidinonilo, 4-hidro-1, 3-tiazolino[3,2a]pirimidinonilo opcionalmente substituido, 1, 2, 3, 4-tetrahidroquinolinilo, 2-tioxo-1, 3-dihidroquinazolinonilo, 1,3- dihidroquinazolindionilo, o benzo[c]azolindionilo, donde el substituyente opcional es seleccionado entre halógeno, alquilo, alcoxi, y nitro; o R8 es fenilo substituido con R22, R23, R24, R25, y R26 fórmula (11), o pirid-2-ilo substituido con R23, R24, R25, y R26 fórmula (12), o pirid-3-ilo substituido con R22 R24, R25, y R26 fórmula (13), o pirid-4-ilo substituido con R22, R23, R25 y R26 fórmula (14), donde R22, R23, R24, R25 y R26 son independientemente seleccionados entre hidrógeno, halógeno, alquilo, hidroxi, alcoxi, alcoxialquilo, dialcoxialquilo, trialcoxialquilo, alcoxiiminoalquilo, alqueniloxiiminoalquilo, alquiniloxiiminoalquilo, cicloalquilalcoxi, alcoxialcoxi, alquiltio, ditioalcoxialquilo, tritioalcoxialquilo, alquilsulfonilo, alquilaminosulfonilo, dialquilaminosulfonilo, cicloalquilaminosulfonilo, alqueniloxi, alquiniloxi, haloalqueniloxi, alquilsulfoniloxi, arilalcoxi opcionalmente substituido, ciano, nitro, amino, alquilamino,alquilcarbonilamino, alcoxicarbonilamino, alqueniloxicarbonilamino, alquiniloxicarbonilamino, haloalquilcarbonilamino, alcoxialcoxicarbonilamino, (alquil)(alcoxicarbonil)amino, alquilsulfonilamino, (heteroaril)(alcoxicarbonil)amino opcionalmente substituido, arilcarbonilamino opcionalmente substituido, formilo, 1,3-dioxolan-2-ilo opcionalmente substituido, 1,3-dioxan-2-ilo opcionalmente substituido, 1,3-oxazolidin-2-ilo opcionalmente substituido, 1,3-oxazaperhidroin-2-ilo opcionalmente substituido, 1,3-ditiolan-2-ilo opcionalmente substituido, 1,3-ditian-2-ilo opcionalmente substituido, alcoxicarbonilo, alquilaminocarboniloxi, alquilaminocarbonilamino, dialquilaminocarbonilamino, alquilamino(tiocarbonil)amino, dialquilfosforoureidilo, tienilo opcionalmente substituido, 1,3-tiazolilalcoxi opcionalmente substituido, arilo opcionalmente substituido, ariloxi opcionalmente substituido, ariloxialquilo opcionalmente substituido, arilaminocarboniloxi opcionalmente substituido, heteroarilo opcionalmente substituido, heteroariloxi opcionalmente substituido, pirrolilo opcionalmente substituido, pirazolilo opcionalmente substituido, piraziniloxi opcionalmente substituido, 1,3-oxazolinilo opcionalmente substituido, 1,3-oxazoliniloxi opcionalmente substituido, 1,3-oxazolinilamino opcionalmente substituido, 1,2,4-triazolilo opcionalmente substituido, 1,2,3-tiadiazolilo opcionalmente substituido, 1,2,5-tiadiazolilo opcionalmente substituido, 1,2,5-tiadiazoliloxi opcionalmente substituido, 2H-tetrazolilo opcionalmente substituido, piridilo opcionalmente substituido, piridiloxi opcionalmente substituido, piridilamino opcionalmente substituido, pirimidinilo opcionalmente substituido, pirimidiniloxi opcionalmente substituido, 3,4,5,6-tetrahidropirimidiniloxi opcionalmente substituido, piridaziniloxi opcionalmente substituido, o 1,2,3,4-tetrahidronaftalenilo opcionalmente substituido, donde el substituyente opcional es seleccionado entre uno o más de halógeno, alquilo, haloalquilo, alcoxi, dialcoxialquilo, ditioalcoxialquilo, ciano, nitro, amino, o alcoxicarbonilamino, siempre que por lo menos uno entre R22, R23, R24, R25, y R26 no es hidrógeno; cuando s es 1; E es un grupo de puente seleccionado entre (CR27R28)x-(CR29R30)y, (CR27R28)x-(CR29R30)yO*, C3H6, C4H8, C(=O), C(=O)C2H4*, C2H4C(=O)*, C3H6C(=O)*,C4H8NHC(=O)*, o C(=S)NH*, donde el asterisco indica la fijación en R8, donde x es 1; y es 0 ó 1; y, donde R27, R28, R29, y R30 son independientemente seleccionados entre hidrógeno, alquilo, y arilo opcionalmente substituido con alcoxi; N-óxidos; y sales agrícolamente aceptables de los mismos.
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