AR035087A1 - Piridil-alquinos y piridil-n-oxido-alquinos herbicidas activos, procedimiento para su preparacion, composicion herbicida y para inhibir el crecimiento de plantas, metodo para el control del crecimiento de plantas indeseables , y metodo para la inhibicion del crecimiento de plantas - Google Patents

Piridil-alquinos y piridil-n-oxido-alquinos herbicidas activos, procedimiento para su preparacion, composicion herbicida y para inhibir el crecimiento de plantas, metodo para el control del crecimiento de plantas indeseables , y metodo para la inhibicion del crecimiento de plantas

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AR035087A1
AR035087A1 ARP020102991A ARP020102991A AR035087A1 AR 035087 A1 AR035087 A1 AR 035087A1 AR P020102991 A ARP020102991 A AR P020102991A AR P020102991 A ARP020102991 A AR P020102991A AR 035087 A1 AR035087 A1 AR 035087A1
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hydrogen
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alkoxy
substituents
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    • 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
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    • C07D213/60Heterocyclic 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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    • C07D213/60Heterocyclic 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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    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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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    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Abstract

Piridil alquinos y piridil-N-óxidos-alquinos herbicidas activos que tienen la fórmula (1) en la que: Z es =N- o fórmula (2), n es 0, 1, 2, 3, 4 o 5; cada R1, independientemente entre sí, es halógeno, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9, -C(R10)=NOR11, -COR12, -OR13, -SR14, -SOR15, -SO2R16, -OSOR17, alquilo C1-8, alquenilo C2-8, alquinilo C2-8 o cicloalquilo C3-6, o es alquilo C1-8, alquenilo C2-8 o alquinilo C2-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(alquil C1-4 tio)=NR26, -OR29, -SR30, -SOR31, -SO2R32 o cicloalquilo C3-6; o cada R1, independientemente entre sí, es cicloalquilo C3-6 sustituido con uno o más sustituyentes de la serie halógeno, -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27 -C(alquil C1-4 tio)=NR28, -SR30, -SOR31, -SO2R32 o cicloalquilo C3-6; o cada R1, independientemente entre sí, es fenilo, que a su vez puede estar sustituido con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o dos R1 adyacentes conjuntamente forman un puente de alquileno C1-7, que puede estar interrumpido por 1 o 2 átomos de oxígeno no vecinos y que puede estar sustituido con alquilo C1-6 o alcoxilo C1-6, donde el número total de átomos del anillo es de por lo menos 5 y como máximo 9; o dos R1 adyacentes conjuntamente forman un puente de alquenileno C2-7, que puede estar interrumpido por 1 o 2 átomos de oxígeno no vecinos y que puede estar sustituido con alquilo C1-6 o alcoxilo C1-6, donde el número total de átomos del anillo es de por lo menos 5 y como máximo 9; R3 y R4 son cada uno, independientemente entre sí, hidrógeno, halógeno, -CN, alquilo C1-4 o alcoxilo C1-4; o R3 y R4 son, conjuntamente, alquileno C2-5; R5 es hidrógeno o alquilo C1-8; R6 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo; donde a su vez el fenilo y el bencilo pueden estar sustituidos con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R5 y R6 son, conjuntamente, una cadena de alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o azufre; R7 es hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o es alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 sustituido con uno o más sustituyentes de la serie halógeno, alcoxilo C1-4 o fenilo, donde a su vez el fenilo puede estar sustituido con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4 sulfonilo; R8 es hidrógeno o alquilo C1-8; R9 es hidrógeno o alquilo C1-8, o es alquilo C1-8 sustituido con uno o más sustituyentes de la serie -COOH, alcoxi C1-8-carbonilo o -CN, o R9 es alquenilo C3-8, alquinilo C3-8 fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R8 yRr9 son, conjuntamente, alquileno C2-5; R10 es hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R11 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R12 es hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R13 es hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8; o R13 es fenilo o fenil-alquilo C1-6, donde ambos anillos de fenilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R13 es alquilo C1-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN, alquil C1-6-amino, di (alquil C1-6)-amino o alcoxilo C1-4; R14 es hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o es alquilo C1-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN o alcoxilo C1-4; R15, R16 y R17 son cada uno, independientemente entre sí, alquilo C1-8, alquenilo C3-8 o alquinilo C3-7, o alquilo C1-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN o alcoxilo C1-4; R18 es hidrógeno o alquilo C1-8; R19 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R18 y R19 son, conjuntamente, una cadena de alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o azufre; R20 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; R21 es hidrógeno o alquilo C1-8; R22 es hidrógeno o alquilo C1-8 o es alquilo C1-8 sustituido con uno o más sustituyentes de la serie -COOH, alcoxi C1-8-carbonilo o -CN, o R22 es alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R21 y R22 son, conjuntamente, alquileno C2-5; R23 es hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R24 es hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R25 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R26 es hidrógeno o alquilo C1-8; R27 es hidrógeno o alquilo C1-8, o es alquilo C1-8 sustituido con uno o más sustituyentes de la serie -COOH, alcoxi C1-8-carbonilo o -CN, o R27 es alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R26 y R27 son, conjuntamente, alquileno C2-5; R28 es hidrógeno o alquilo C1-8; R29 y R30 son cada uno, independientemente entre sí, hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN o alcoxilo C1-4; R31 y R32 son cada uno, independientemente entre sí, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 sustituido con uno o más sustituyentes de la serie halógeno, -CN o alcoxilo C1-4; m es 0, 1, 2, 3 o 4; cada R2 es, independientemente entre sí, halógeno, -CN, -SCN, -OCN, -N3, -SF5, -NO2, -NR33R34, -CO2R35, -CONR37R37, -C(R38)=NOR39, -COR40, -OR41, -SR42, -SOR43, -SO2R44, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61, -CR62(OR63)OR64, -OC(O)NR65R66, -SC(O)N-R67R68, -OC(S)NR69R70 o N-ftalimida; o R2 es un sistema anular heterocíclico de 5 a 7 miembros que puede ser aromático o parcial o totalmente saturado y que puede contener de 1 a 4 heteroátomos seleccionados entre nitrógeno, oxígeno y azufre, donde es posible que dicho sistema anular heterocíclico esté a su vez sustituido con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, hidroxialquilo C1-4, alcoxilo C1-4, alcoxi C1-4-alquilo C1-4, -CN, -NO2, alquil C1-6-tio, alquil C1-6-sulfinilo o alquil C1-6-sulfonilo; R33 es hidrógeno o alquilo C1-8; y R34 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R33 y R34 son, conjuntamente, una cadena de alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o azufre; R35 es hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o es alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 sustituidos con uno o más sustituyentes de la serie halógeno, alcoxilo C1-4 o fenilo, donde a su vez el fenilo puede estar sustituido con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo, R36 es hidrógeno o alquilo C1-8; R37 es hidrógeno o alquilo C1-8, o es alquilo C1-8 sustituido con uno o más sustituyentes de la serie -COOH, alcoxi C1-8-carbonilo o -CN, o R37 es alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, donde el fenilo y el bencilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; o R36 y R37 son, conjuntamente, alquileno C3-5; R38 es hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R39 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R40 es hidrógeno, alquilo C1-4, haloalquilo C1-4, alquil C1-8-tio, -C(O)-C(O)O- alquilo C1-4 o cicloalquilo C3-8, R41 es hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, alcoxi C1-6-alquilo C1-6, alquil C1-8-carbonilo, alcoxi C1-8-carbonilo, alqueniloxi C3-8-carbonilo, alcoxi C1-6-alcoxi C1-6-carbonilo, alquil C1-6-tio-alquilo C1-6, alquil C1-6-sulfinil-alquilo C1-6 o alquil C1-6-sulfonil-alquilo C1-6; o R41 es fenilo o fenil-alquilo C1-6, donde ambos anillos de fenilo pueden estar sustituidos a su vez con uno o más sustituyentes de la serie halógeno, alquilo C1-4, haloalquilo C1-4, alcoxilo C1-4, -CN, -NO2 o -S(O)2-alquilo C1-8; o R41 es alquilo
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