AR043065A1 - Piperazinas y piperidinas n-(arilmetil substituidas) 4-(metil disubstituidas) - Google Patents

Piperazinas y piperidinas n-(arilmetil substituidas) 4-(metil disubstituidas)

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AR043065A1
AR043065A1 ARP030104689A ARP030104689A AR043065A1 AR 043065 A1 AR043065 A1 AR 043065A1 AR P030104689 A ARP030104689 A AR P030104689A AR P030104689 A ARP030104689 A AR P030104689A AR 043065 A1 AR043065 A1 AR 043065A1
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Argentina
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optionally substituted
alkyl
formula
substituted
hydrogen
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ARP030104689A
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Fmc Corp
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    • C07D405/00Heterocyclic 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
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    • C07D241/52Oxygen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P33/00Antiparasitic agents
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C07D211/08Heterocyclic 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
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    • C07D211/06Heterocyclic 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
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    • C07D211/20Heterocyclic 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
    • C07D211/22Heterocyclic 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
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    • C07D211/08Heterocyclic 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
    • C07D211/18Heterocyclic 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
    • C07D211/20Heterocyclic 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
    • C07D211/24Heterocyclic 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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    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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
    • C07D211/18Heterocyclic 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
    • C07D211/26Heterocyclic 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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    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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
    • C07D211/18Heterocyclic 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
    • C07D211/26Heterocyclic 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
    • C07D211/28Heterocyclic 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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    • C07D211/18Heterocyclic 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
    • C07D211/30Heterocyclic 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
    • C07D211/32Heterocyclic 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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    • C07D211/94Oxygen atom, e.g. piperidine N-oxide
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Abstract

Las composiciones que comprenden una cantidad insecticidamente efectiva de al menos un compuesto de fórmula (1), y opcionalmente, una cantidad efectiva de al menos uno de un segundo compuesto, con al menos un vehículo insecticidamente compatible también se encuentran revelados en la presente; junto con los métodos para controlar los 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 CH o N, formando un anillo de azina de seis miembros seleccionado entre piperidina, y piperazina; R2, R3, R4, R5, y R6 están independientemente seleccionados entre hidrógeno, halógeno, alquilo, haloalquilo, hidroxilo, alcoxi, haloalcoxi, pentahalotio, alquiltio, ciano, nitro, alquilcarbonilo, alcoxicarbonilo, arilo, o ariloxi, o cada uno de R2 y R3, o R3 y R4 están tomadas juntas con -OCF2O-,-OCF2CF2-, -CF2CF2O-, o -CH=CHCH=CH-, formando un anillo benzo-fusionado; siempre que cuando, (a) m y n son 0; se forma un grupo carbonilo con carbono de metilo (a) fórmula (2), donde B es O; (b) m es 0 y n es 1; (i) B y R1 están tomadas juntas con -G-CH(R14)-(CH2)v-J- y con carbono de metilo (a), se forma un anillo heterocíclico; fórmula (3), G y J están independientemente seleccionadas entre O ó S; v es 1 o 2;está seleccionada entre hidrógeno o arilo opcionalmente substituido con halógeno o haloalquilo; o, ii) A es N, se forma un anillo de piperazina, y uniones dobles entre el carbono de metilo (a) y se forman la posición 4 del anillo de piperazina y a sus otros substituyentes fórmula (4); donde B es fenilo substituido con R9, R10, R11, R12, y R13 fórmula (5), donde R9, R10, R11, R12, y R13 están independientemente seleccionados entre hidrógeno, halógeno, alquilo, haloalquilo, hidroxilo, alcoxi, haloalcoxi, mercapto, y alquiltio, ciano, alquilcarbonilo, alcoxicarbonilo, o ariloxi; y, donde cualquiera de R9 y R10, o R10 y R11 pueden ser tomados juntos con -OCF2O-, -OCF2CF2-,o -CF2CF2O-, formando un anillo benzo-fusionado; y R1 está seleccionado entre hidrógeno, alquilo, alcoxialquilo, o arilo; (c) m es 1 y n es 0; se forma una unión doble entre el carbono de metilo (a) y B fórmula (6), donde B es un grupo de puente desde el carbono de metilo (a) a R, y está seleccionado entre CH-, NN=*, nnr15*, NNR15CH2*, NNR15C(=O)*, NNR15SO2*, NNR15C(=O)NR16*, Y NNR15C(=S)NR16*, donde el asterisco denota la unión a R; donde R15 y R16 estás independientemente seleccionados entre hidrógeno, alquilo, alquilaminocarbonilo, y arilcarbonilo donde el arilo está 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 (7); o R es pirid-2-ilo substituido con R18, R19, R20, y R21 fórmula (8), o pirid-3-ilo substituido con R17, R19, R20 y R21 fórmula (9), o pirid-4-ilo substituido con R17, R18, R20 y R21 fórmula (10), o piridazin-3-ilo substituido con R19, R20 y R21 fórmula (11), donde R17, R18, R19, R20, y R21 están 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 de R17 y R18, o R18 y R19 pueden ser tomados juntos con -OCF2O-,-OCF2CF2-, -CF2CF2O-, o -CH2CH=CHCH2-, formando un anillo benzo-fusionado; A es N, se forma un anillo de piperazina, y se forman las uniones dobles entre el carbono de metilo (a) y la posición 4 del anillo de piperazina y a sus otros substituyentes fórmula (12); donde B es un grupo 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 denota la unión al carbono de metilo (a); donde R15 y R16 están descriptas más arriba; donde R y R1 están descriptas más arriba; cuando p es 1, 2, o 3; D es -CH2-, y se forma un derivado azabiciclo del anillo de azina de seis miembros; cuando q es 0, y r es 1, se forma un derivado de óxido-N del nitrógeno del anillo de azina de seis miembros; cuando q es 1 y r es 0 ó 1; R7 está seleccionado entre alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, dialquilaminoalquilo, alquilaminocarboniloxialquilo, alquiltioalquilo, alquilsulfonilalquilo, alquilcarboniloxialquilo, alcoxicarbonilalquilo, carboxialquilo, arilalquilo, arilcarbonilo, sulfonato, o sulfonatoalquilo, y puede soportar una carga negativa que resulta en una sal interior; y un ión separado es cloruro, bromuro, ioduro, o un alquil o fenil sulfato o sulfonato; 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 está seleccionado entre halógeno, alquilo, alcoxi, y nitro; o R8 es fenilo substituido con R22, R23, R24, R25, y R26 fórmula (13), o pirid-2-ilo substituido con R23, R24, R25, y R26 fórmula (14), o pirid-3-ilo substituido con R22 R24, R25, y R26 fórmula (15), o pirid-4-ilo substituido con R22, R23, R25 y R26 fórmula (16), donde R22, R23, R24, R25 y R26 están 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 está 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 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 denota la unión a0 R8, donde x es 1; y es 0, o 1; y, donde R27, R28, R29, y R30 están independientemente seleccionados entre hidrógeno, alquilo, y arilo opcionalmente substituido con alcoxi; N-óxidos; y sales agrícolamente aceptables de los mismos; con la salvedad que cuando A es N, formando dicho anillo de piperazina; s es 0 ó 1; y cuando s es 1 E es dicho grupo puente C(=O), o -(CR27R28)x-(CR29R30)y- donde x es 1, y es 0, y R27 y R28 son hidrógeno, y R8 está seleccionado entre indolilo opcionalmente substituido, arilpirazolilo opcionalmente substituido, y benzo[b]tiofenilo opcionalmente substituido; o, R8 es fenilo substituido con R22, R23, R24, R25, y R26 donde R22, R23, R25, y R26 son hidrógeno; y R24 está seleccionado entre hidrógeno, halógeno, alquilo, hidroxi, alcoxi, cicloalquilalcoxi, arilalcoxi opcionalmente substituido, ciano, nitro alquilamino, alcoxicarbonilamino, (alquil)(alcoxicarbonil)amino, (heteroaril)(alcoxicarbonil)amino, alcoxicarbonilo, ariloxi opcionalmente substituido, 1,2,5-tiadiazolilo
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