AR067116A1 - Compuestos derivados de piperazina utiles como agentes herbicidas y procedimiento para combatir el crecimiento indeseado de plantas. - Google Patents

Compuestos derivados de piperazina utiles como agentes herbicidas y procedimiento para combatir el crecimiento indeseado de plantas.

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AR067116A1
AR067116A1 ARP080102673A ARP080102673A AR067116A1 AR 067116 A1 AR067116 A1 AR 067116A1 AR P080102673 A ARP080102673 A AR P080102673A AR P080102673 A ARP080102673 A AR P080102673A AR 067116 A1 AR067116 A1 AR 067116A1
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alkyl
alkynyl
alkenyl
cycloalkyl
cycloalkenyl
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Basf Se
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    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
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    • 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
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    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
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  • Zoology (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicacion 1: Compuestos de piperazina de la formula 1 caracterizados porque A1, A2 son, de modo independiente entre sí, arilo o heteroarilo, en donde Ra está unido en posicion orto respecto del sitio de union de A1 con un átomo de C o átomo de N de A1, Y1 es oxigeno, azufre o un grupo NRi1, en donde Ri1 está seleccionado de hidrogeno, alquilo C1-6, alquenilo C3-6, alquinilo C3-6, cicloalquilo C3-6, cicloalquil C3-6-metilo, OH, alcoxi C1-6, alquenil C3-6-oxi, alquinil C3-6-oxi, cicloalcoxi C3-6 y cicloalquil C3-6-metoxi; Y2 es oxigeno, azufre o un grupo NRi2, en donde Ri2 está seleccionado de hidrogeno, alquilo C1-6, alquenilo C3-6, alquinilo C3-6, cicloalquilo C3-6, cicloalquil C3-6-metilo, OH, alcoxi C1-6, alquenil C3-6-oxi, alquinil C3-6-oxi, cicloalcoxi C3-6 y cicloalquil C3-6-metoxi; en donde las partes alifáticas o cíclicas mencionadas de los sustituyentes Y1 e Y2 no están sustituidas, pueden estar parcial o completamente halogenadas y/o pueden llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; Ra está seleccionado de halogeno, ciano, nitro, SF5, alquilo C1-6, cicloalquilo C3-6, alquenilo C2--6, cicloalquenilo C5-8, cicloalquinilo C5-8, cicloalquil C3-6-alquilo C1-6, cicloalquenil C5-8-alquilo C1-6, cicloalquinil C5-8-alquilo C1-6, cicloalquil C3-6-alquenilo C2-6, cicloalquenil C5-8-alquenilo C2-6, cicloalquinil C5-8-alquenilo C2-6, cicloalquil C3-6-alquinilo C2-6, cicloalquenil C5-8-alquinilo C2-6, cicloalquinil C5-8-alquinilo C2-6, alcadienilo C4-10, alquinilo C2-6, [tri-alquil (C1-6)-silil]-alquinilo C2-6, tri-alquil C1-6-sililo, cicloalquinilo C7-8, arilo, fenil-alquilo C1-6, fenil-alquenilo C2-6, fenil-alquinilo C2-6, fenilsulfonil-alquilo C1-6, heterociclilo, heterociclil-alquilo C1-6, heterociclil-alquenilo C2-6, heterociclil-alquinilo C2-6, fenil-[alcoxi C1-6-carbonil]-alquilo C1-6, Z1P(O)(OR9)2, Z1P(O)(OR9)(R9a), Z2B(OR10)2, Z3COR11, Z4NR12R13, Z5CH=N-O-R14, Z6OR15, Z7SR16, Z7S(O)R16 y Z7SO2R16, en donde las partes alifáticas, cíclicas o aromáticas mencionadas del sustituyente Ra no están sustituidas, pueden estar parcial o completamente halogenadas y/o pueden llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; Rb, Rc, Rd, Re y Rf representan en cada caso, de modo independiente entre sí, hidrogeno o presentan uno de los significados indicados para Ra; y en donde dos radicales Ra unidos a átomos de anillo adyacentes, de A1, Rb o Rc o dos radicales Rd unidos a átomos de anillo adyacentes de A2, Re o Rf también pueden ser alquileno C3-6, que puede ser parcial o totalmente halogenado y que puede llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; en donde un grupo CH2 en alquileno C3-6 puede estar reemplazado por un grupo carbonilo, un grupo tiocarbonilo o sulfonilo y en donde uno o dos grupos CH2 no adyacentes en alquileno C3-6 pueden estar reemplazados, en cada caso, por oxígeno, azufre o un grupo NR34, en donde R34 presenta uno de los significados indicados para R12; R1 y R2 están seleccionados, de modo independiente entre sí, de: ciano, alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, cicloalquenilo C5-8, alquinilo C3-6, cicloalquinilo C7-8, cicloalquil C3-6-alquilo C1-6, cicloalquenil C5-8-alquilo C1-6, cicloalquinil C5-8-alquilo C1-6, cicloalquil C3-6-alquenilo C2-6, cicloalquenil C5-8-alquenilo C2-6, cicloalquinil C3-6-alquenilo C2-6, cicloalquil C3-6-alquinilo C2-6, cicloalquenil C5-8-alquinilo C2-6, cicloalquinil C5-8-alquinilo C2-6, fenilo, fenil-alquilo C1-6, fenil-alquenilo C2-6, fenil-alquinilo C2-6, heterociclilo, heterociclil-alquilo C1-6, heterociclil-alquenilo C2-6, heterociclil-alquinilo C2-6, fenil-[alcoxi C1-6-carbonil]-alquilo C1-6, C(O)R21, NR22R23, OR24, SR24, S(O)R25, SO2R25 y Si(R25a)3; en donde R1 puede significar adicionalmente hidrogeno, y en donde las partes alifáticas, cíclicas o aromáticas mencionadas de los sustituyentes R1 y R2 de modo independiente entre sí no están sustituidas, pueden estar parcial o completamente halogenadas y/o pueden llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; R3 es halogeno, ciano, nitro o un radical R26, OR27, SR28, S(O)R28, SO2R28, NR29R30 o N(OR31)R32; R4 es hidrogeno, halogeno, ciano, alquilo C1-6, cicloalquilo C3-6, alquenilo C2-6, cicloalquenilo C5-8, alquinilo C2-6, cicloalquinilo C5-8, fenilo, fenil-alquilo C1-6, heterociclilo, heterociclil-alquilo C1-6, fenil-[alcoxi C1-6-carbonil]-alquilo C1-6, o un radical COR21, OR27, SR28, S(O)R28, SO2R26, NR29R30 o N(OR31)R32, en donde las partes alifáticas, cíclicas o aromáticas mencionadas del sustituyente R4 de modo independiente entre si no están sustituidas, pueden estar parcial o completamente halogenadas y/o pueden llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; R5 es hidrogeno, halogeno, ciano, nitro, hidroxi, alquilo C1-8, alquenilo C2-8, cicloalquilo C3-8, cicloalquenilo C5-8, alquinilo C2-8, alcadienilo C4-8, cicloalquinilo C7-8, cicloalquenil C5-8-alquilo C1-6, cicloalquinil C5-8-alquilo C1-6, cicloalquil C3-6-alquenilo C2-6, cicloalquenil C5-8-alquenilo C2-6, cicloalquinil C5-8-alquenilo C2-6, cicloalquil C3-6-alquinilo C2-6, cicloalquenil C5-8-alquinilo C2-6, cicloalquinil C5-8-alquinilo C2-6, tri-alquil C1-6-sililo, [tri-alquil C1-6-silil]-alquinilo C2-6, fenilo, fenil-alquilo C1-6, fenil-alquenilo C2-6, fenil-alquinilo C2-6, heterociclilo, heterociclil-alquilo C1-6, heterociclilalquenilo C2-6, heterociclil-alquinilo C2-6, fenil-[alcoxi C1-6-carbonil]-alquilo C1-6, C(O)R61, Z8NR62R63, Z11CH=N-O-R64, OR65, Z9SR65a, Z9S(O)R66, Z9S(O)2R66 o Z10P(O)(OR67)2; o R3 junto con R5 es un enlace químico; R6 es halogeno, ciano, nitro, alquenilo C2-8, cicloalquilo C3-8, cicloalquenilo C5-8, alquinilo C2-8, alcadienilo C4-8, cicloalquinilo C7-8, cicloalquenil C5-8-alquilo C1-6, cicloalquinil C5-8-alquilo C1-6, cicloalquil C3-6-alquenilo C2-6, cicloalquenil C5-8-alquenilo C2-6, cicloalquinil C5-8-alquenilo C2-6, cicloalquil C3-6-alquinilo C2-6, cicloalquenil C5-8-alquinilo C2-8, cicloalquinil C5-8-alquinilo C2-6, tri-alquil C1-6-sililo, [tri-alquil C1-6-silil]-alquinilo C2-6, fenilo, fenil-alquilo C1-6, fenil-alquenilo C2-6, fenil-alquinilo C2-6, heterociclilo, heterociclil-alquilo C1-6, heterociclil-alquenilo C2-6, heterociclil-alquinilo C2-6, fenil-[alcoxi C1-6--carbonil]-alquilo C1-6, C(O)R61, Z8NR62R63, Z11CH=N-O-R64, OR65, Z9SR65a, Z9S(O)R66, Z9S(O)2R66 o Z10P(O)(OR67)2; en donde las partes alifáticas, cíclicas o aromáticas mencionadas de los sustituyentes R4, R5 y R6 de modo independiente entre sí pueden estar parcial o completamente halogenadas y/o pueden llevar uno a tres de los siguientes grupos: ciano, hidroxi, alquilo C1-4, halogenalquilo C1-4, cicloalquilo C3-6, alcoxi C1-4, alquil C1-4-tio, di-(alquil C1-4)-amino, alquil C1-4-carbonilo, hidroxicarbonilo, alcoxi C1-4-carbonilo, aminocarbonilo, alquil C1-4-aminocarbonilo, di-(alquil C1-4)aminocarbonilo o alquil C1-4-carboniloxi; R7 es halogeno, ciano, nitro o un radical R26, OR27, SR28, S(O)R28, SO2R28, NR29R30 o N(OR31)R32; R8 presenta uno de los significados indicados para R4; R9, R10 y R67 son de modo independiente entre si, hidrogeno o alquilo C1-6 y R10 en Z2B(OR10)2 pueden formar juntos una cadena de alquileno C2-4; o R9a es alquilo C1-6; R11, R61 son, de modo independiente entre si, hidrogeno, alquilo C1-6, cicloalquilo C3-6, alquenilo C2-6, cicloalquenilo C5-8, alquinilo C2-6, cicloalquinilo C7-8, hidroxi, alcoxi C1-6, alquenil C3-6-oxi, alquinil C3-6-oxi, amino, alquil C1-6-amino, di-(alquil C1-6)amino, alcoxi C1-6-amino, di-(alcoxi C1-6)amino, alquil C1-6-sulfonilamino, alquil C1-6aminosulfonilamino, [di-(aIquil C1-6)amino]sulfonilamino, alquenil C3-6-amino, alquinil C3-6-amino, N-(alquenil C2-6)-N-(alquil C1-6)-amino, N-(alquinil C2-6)-N-(alquil C1-6)-amino, N-(alcoxi C1-6)-N-(alquil C1-6)-amino, N-(alquenil C2-6)-N-(alcoxi C1-6)-amino, N-(alquinil C2-6)-N-(alcoxi C1-6)-amino, fenilo, fenoxi, fenilamino, naftilo o heterociclilo, R12 y R62 son, de modo independiente entre sí, hidrogeno, alquilo C1-6, alcoxi C1-6, cicloalquilo C3-6, cicloalquil C3-6-oxi, alquenilo C3-6, alquenil C3-6-oxi, cicloalquenilo C5-8, alquinilo C3-6, alquinil C3-6-oxi, cicloalquinilo C7-8, alquil C1-6-carbonilo, cicloalquil C3-6-carbonilo, di-(alquil C1-6)aminocarbonilo, alcoxi C1-6-carbonilo, alcoxi C1-6-carbonil-alquilo C1-6, alquil C1-6-sulfonilo, alquil C1-6-aminosulfonilo, di-(alquil C1-6)aminosulfonilo, fenilcarbonilo, fenilaminocarbonilo, fenilsulfonilo, fenilsulfonilaminocarbonilo o heterociclilcarbonilo; R13 y R63 son, de modo independiente entre si, hidrogeno, alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, cicloalquenilo C5-8, alquinilo C3-6,
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