AR031243A1 - Piridincetonas herbicidamente activas, procedimiento para su preparacion, agentes herbicidas y para inhibir el desarrollo de las plantas, procedimiento para combatir el crecimiento no deseado de plantas, procedimiento para inhibir el crecimiento no deseado de plantas y compuestos utiles como interme - Google Patents

Piridincetonas herbicidamente activas, procedimiento para su preparacion, agentes herbicidas y para inhibir el desarrollo de las plantas, procedimiento para combatir el crecimiento no deseado de plantas, procedimiento para inhibir el crecimiento no deseado de plantas y compuestos utiles como interme

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AR031243A1
AR031243A1 ARP010102734A ARP010102734A AR031243A1 AR 031243 A1 AR031243 A1 AR 031243A1 AR P010102734 A ARP010102734 A AR P010102734A AR P010102734 A ARP010102734 A AR P010102734A AR 031243 A1 AR031243 A1 AR 031243A1
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Argentina
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alkyl
alkoxy
thio
sulfinyl
sulfonyl
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D401/06—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
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C07D405/02—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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • C07D417/02—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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Piridincetonas herbicidamente activas, que tienen la formula (1), en la cual: p significa 0 o 1; R1 representa una cadena de alquileno C1-6, alquenileno C3-6 o alquinileno C3-6, que puede estar substituida de forma sencilla o multiple por halogeno o R5, no estando los enlaces no saturados de la cadena unidos directamente a los substituyentes X1; X1 significa oxígeno, -O(CO)-, -(CO)O-, -O(CO)O-, -N(R6)-O-, -ONR51-, tio, sulfinilo, sulfonilo, -SO2NR7-, -NR52SO2- o -NR8-; R2 representa un grupo alquilo C1-8, alquenilo C3-6 o alquinilo C3-6, que están substituidos de forma sencilla o multiple por halogeno, hidroxilo, amino, formilo, nitro, ciano, mercapto, carbamoílo, alcoxilo C1-6, alcoxi C1-6-carbonilo, alquenilo C2-6, halogenoalquenilo C2-6, alquinilo C2-6, halogenoalquinilo C2-6, cicloalquilo C3-6, cicloalquilo C3-6 substituido por halogeno, o por alqueniloxilo C3-6, alquiniloxilo C3-6, halogenoalcoxilo C1-6, halogenoalquenil-oxilo C3-6, cianoalcoxilo C1-6, alcoxi C1-6-alcoxilo C1-6, alcoxi C1-6-alcoxi C1-6-alcoxilo C1-6, alquil C1-6-tio-alcoxilo C1-6, alquil C1-6-sulfinil-alcoxilo C1-6, alquil C1-6-sulfonil-alcoxilo C1-6, alcoxi C1-6-carbonil-alcoxilo C1-6, alcoxi C1-6-carbonilo, alquil C1-6-carbonilo, alquil C1-6-tio, alquil C1-6-sulfinilo, alquil C1-6-sulfonilo, halogenoalquil C1-6-tio, halogenoalquil C1-6-sulfinilo, halogenoalquil C1-6-sulfonilo, oxiranilo, que a su vez puede estar substituido por alquilo C1-6 o por (3-oxetanil)-oxilo, que a su vez puede estar substituido por alquilo C1-6, o por benciltio, bencilsulfinilo, bencilsulfonilo, alquil C1-6-amino, di-(alquil C1-6)-amino, R9S(O)2O, R10N(R11)SO2, rodano, fenilo, fenoxilo, feniltio, fenilsulfinilo o fenilsulfonilo; pudiendo estar los grupos que contienen fenilo o bencilo a su vez substituidos por uno o más grupos alquilo C1-6, halogenoalquilo C1-6, alcoxilo C1-6, halogenoalcoxilo C1-6, halogeno, ciano, hidroxilo o nitro; o R2 representa fenilo, que puede estar substituido una o varias veces por alquilo C1-6, halogenoalquilo C1-6, alcoxilo C1-6, halogenoalcoxilo C1-6, halogeno, ciano, hidroxilo o nitro; o R2 representa cicloalquilo C3-6, cicloalquilo C3-6 substituido por alcoxilo C1-6 o alquilo C1-6, 3-oxetanilo o 3-oxetanilo substituido por alquilo C1-6; o cuando Q representa Q2 o Q3 o cuando representa Q1, en los cuales R14 y R22 significan una cadena de alquileno C2-3, R2 representa adicionalmente también un sistema anular monocíclico o bicíclico condensado de 5 a 10 miembros, que puede ser aromático, saturado o parcialmente saturado y que puede contener de 1 a 4 heteroátomos seleccionados del grupo formado por nitrogeno, oxígeno y azufre, estando unido el sistema anular directamente o por medio de un grupo alquileno C1-4, alquenil C2-4-alquileno C1-4, alquinil C2-4-alquileno C1-4, -N(R12)-alquileno C1-4, -SO-alquileno C1-4 o -SO2-alquileno C1-4 a los substituyentes X1, no pudiendo contener cada sistema anular más de 2 átomos de oxígeno ni más de 2 átomos de azufre, estando el sistema anular mismo sustituido una, dos o tres veces por alquilo C1-6, halogenoalquilo C1-6, alquenilo C2-6, halogenoalquenilo C2-6, alquinilo C2-6, halogenoalquinilo C2-6, alcoxilo C1-6, hidroxilo, halogenoalcoxilo C1-6, alqueniloxilo C3-6, alquiniloxilo C3-6, mercapto, alquil C1-6-tio, halogenoalquil C1-6-tio, alquenil C3-6-tio, halogenoalquenil C3-6-tio, alquinil C3-6-tio, alcoxi C2-5-alquiltio, acetilalquil C3-5-tio, alcoxi C3-6-carbonilalquiltio, cianoalquil C2-4-tio, alquil C1-6-sulfinilo, halogenoalquil C1-6-sulfinilo, alquil C1-6-sulfonilo, halogenoalquil C1-6-sulfonilo, aminosulfonilo, alquil C1-2-aminosulfonilo, di(alquil C1-2)-aminosulfonilo, di-(alquil C1-4)-amino, halogeno, ciano, nitro, fenilo y benciltio, pudiendo estar sustituido a su vez el fenilo y el benciltio en el anillo fenolico por alquilo C1-3, halogenoalquilo C1-3, alcoxilo C1-3, halogenoalcoxilo C1-3, halogeno, ciano o nitro, siendo los sustituyentes en el nitrogeno en el anillo heterocíclico distintos de halogeno; o R2 representa hidrogeno o alquilo C1-8 sin sustituir, cuando: (a) R1 está sustituido por el grupo R5, o (b) Q representa el grupo Q2, o (c) Q representa el grupo Q3, en el cual X1 significa -O(CO)-, -(CO)O-, -N(R6)-O-, -ONR51-, -SO2NR7-, -NR52SO2- o -NR8-, o (d) Q representa el grupo Q1, en el cual X1 significa -N(R6)-O-, -ONR51-, -SO2NR7-, -NR52SO2- o -NR8-, o (e) Q representa el grupo Q1, en el cual R14 y R22 en Q1 significan una cadena de alquileno C2-3 y X1 -O(CO)- o -(CO)O-; R3 significa halogenoalquilo C1-3; R4 significa hidrogeno, halogeno, alquilo C1-3, halogenoalquilo C1-3, alcoxilo C1-3, alcoxi C1-3-alquilo C1-3 o alcoxi C1-3-alcoxilo C1-3; R5 representa hidroxilo, alcoxilo C1-6, cicloalcoxilo C3-6, alcoxi C1-6-alcoxilo C1-6, alcoxi C1-6-alcoxi C1-6-alcoxilo C1-6 o alquil C1-2-sulfoniloxilo; R6, R7, R8, R9, R10, R11, R12, R51 y R52 significan independientemente entre sí hidrogeno, alquilo C1-6, halogenoalquilo C1-6, alcoxi C1-6-carbonilo, alquil C1-6-carbonilo, alcoxi C1-6-alquilo C1-6, alcoxi C1-6-alquilo C1-6 sustituido por alcoxilo C1-6, bencilo o fenilo, pudiendo estar sustituido a su vez el fenilo y bencilo una o varias veces por alquilo C1-6, halogenoalquilo C1-6, alcoxilo C1-6, halogenoalcoxilo C1-6, halogeno, ciano, hidroxilo o nitro, no representando al mismo tiempo R6 hidrogeno y R9 hidrogeno, alcoxi C1-6-carbonilo o alquil C1-6-carbonilo; Q representa Q1, en la cual: A1 significa C(R14R15), NR16 u oxígeno; A2 significa C(R17R18), C(O), -C=N-O-R19, oxígeno, tio, sulfinilo, sulfonilo, NR20 o etileno, con las condiciones de que A1 sea distinto de oxígeno cuando A2 representa oxígeno, C(O), tio, sulfinilo, -C=N-O-R19, NR20 o C(R17R18), significando R17 y R18, independientemente entre sí, alcoxilo C1-4, alquil C1-4-tio, alquil C1-4-sulfinilo, alquil C1-4-sulfonilo y de que A1 sea distinto de NR16 cuando A2 representa tio, sulfinilo o C(R17R18), significando R17 y R18, independientemente entre sí, alcoxilo C1-4, alquil C1-4-tio, alquil C1-4-sulfinilo, alquil C1-4-sulfonilo; R14 y R22 representan, independientemente entre sí, hidrogeno, alquilo C1-4, haloalquilo C1-4, alquenilo C3-4, alquinilo C3-4, alquil C1-4-tio, alquil C1-4-sulfinilo, alquil C1-4-sulfonilo, alquil C1-4-sulfoniloxilo, alcoxilo C1-4, alcoxi C1-4-carbonilo o alquil C1-4-carbonilo; R15 y R21 significan independientemente entre sí, hidrogeno, alquilo C1-4, halogenoalquilo C1-4, alquenilo C3-4 o alquinilo C3-4; R17 significa hidrogeno, alquilo C1-4, halogenoalquilo C1-4, alcoxilo C1-4, alquil C1-4-tio, alquil C1-4-sulfinilo o alquil C1-4-sulfonilo; R18 significa hidrogeno, alquilo C1-4, halogenoalquilo C1-4, alquenilo C3-4, alquinilo C3-4, alcoxilo C1-4, alquil C1-4-tio, alquil C1-4-sulfinilo, alquil C1-4-sulfonilo o dialcoxialquil C1-4-alquilo C1-4; R20 significa alquilo C1-4, cicloalquilo C3-6, alquenilo C3-4, alquinilo C3-4, alquil C1-4-carbonilo, alquil C1-4-carboniloxilo, di-(alquil C1-4)-aminocarbonilo o bencilo, pudiendo estar el grupo fenilo sustituido una o varias veces por alquilo C1-6, halogenoalquilo C1-6, alcoxilo C1-6, halogenoalcoxilo C1-6, halogeno, ciano, hidroxilo o nitro; R19 y R16 significan, independientemente entre sí, hidrogeno, alquilo C1-4, cicloalquilo C3-6, alquenilo C3-4, alquinilo C3-4, bencilo o fenilo, pudiendo estar el grupo fenilo y bencilo a su vez sustituido una o varias veces por alquilo C1-6, halogenoalquilo C1-6, alcoxilo C1-6, halogenoalcoxilo C1-6, halogeno, ciano, hidroxilo o nitro; o R14 y R22 forman conjuntamente una cadena de alquileno C2-3; o R14 y R15 conjuntamente y/o R17 y R18 conjuntamente y/o R21 y R22 conjuntamente forman una cadena de alquileno C2-4, que puede estar interrumpida por oxígeno y/o carbonilo y/o azufre, con la condicion de que el átomo de oxígeno y el átomo de azufre estén separados por al menos un grupo metileno; o R14 y R18 forman conjuntamente una cadena de alquileno C2-4; o R22 y R18 forman conjuntamente una cadena de alquileno C2-4; o R18 forma conjuntamente con R22 o R14 un enlace directo; o R16 y R18 forman conjuntamente una cadena de alquileno C2-4; R13 significa hidroxilo, O-M+, en el cual M+ representa un cation de metal alcalino o un cation de amonio, halogeno, alquil C1-12-sulfoniloxilo, amino, alquil C1-4-tio, alquil C1-12-sulfinilo, alquil C1-12-sulfonilo, halogenoalquil C1-12-tio, halogenoalquil C1-12-sulfinilo, halogenoalquil C1-12-sulfonilo, alcoxi C1-6-alquil C1-6-tio, alcoxi C1-6-alquil C1-6-sulfinilo, alcoxi C1-6-alquil C1-6-sulfonilo, alquenil C3-12-tio, alquenil C3-12-sulfinilo, alquenil C3-12-sulfonilo, alquilnil C3-12-tio, alquinil C3-12-sulfinilo, alquinil C3-12-sulfonilo, alcoxi C1-4-carbonil-alquil C1-4-tio, alcoxi C1-4-carbonil-alquil C1-4-sulfinilo, alcoxi C1-4-carbonil-alquil C1-4-sulfonilo, (alcoxi C1-4)2P(O)O, alquil C1-4-(alcoxi C1-4)P(O)O, H-(alcoxi C1-4)P(O)O, R23R24N, R25R26NNH, R27R28NC(O)O-, R29R30NC(O)NH-, alquil C1-18-carboniloxilo, alquenil C2-18-carboniloxilo, alquinil C2-18-carboniloxilo, cicloalquil C3-6-carboniloxilo, alcoxi C1-12-carboniloxilo, alquil C1-12-tio-carboniloxilo, alquil C1-12-tiocarbamoílo, pudiendo los grupos alquilo, alquenilo y alquinilo estar substituidos por halogeno, alcoxilo C1-6, alquil C1-6-tio, alquil C1-6-sulfinilo, alquil C1-6-sulfonilo o ciano; o R13 representa fenoxilo, feniltio, fenilsulfinilo, fenilsulfonilo, fenilsulfonilamino, fenilsulfoniloxilo o benzoiloxilo, pudiendo estar los grupos fenilo substituidos a su vez por uno o varios grupos halogeno, nitro, ciano, alquilo C1-4, halogenoalquilo C1-4, alcoxilo C1-4 o halogenoalcoxilo C1-4; o R13 significa un grupo het1-tio, het2-sulfinilo, het3-sulfonilo, het4-(CO)O o het5-N(R33), en los cuales het1, het2, het3, het4 o het5 representan, independientemente entre sí, un sistema anular monocíclico o bicíclico condensado de 5 a 10 miembros, que puede ser aromático o parcialmente saturado y contener de 1 a 4 heteroátomos seleccionados del grupo formado por nitrogeno, oxígeno y azufre, no pudiendo contener cada sistema anular
ARP010102734A 2000-06-09 2001-06-07 Piridincetonas herbicidamente activas, procedimiento para su preparacion, agentes herbicidas y para inhibir el desarrollo de las plantas, procedimiento para combatir el crecimiento no deseado de plantas, procedimiento para inhibir el crecimiento no deseado de plantas y compuestos utiles como interme AR031243A1 (es)

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