AR082987A1 - Arilpirrolidinas pesticidas - Google Patents

Arilpirrolidinas pesticidas

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Publication number
AR082987A1
AR082987A1 ARP110103347A ARP110103347A AR082987A1 AR 082987 A1 AR082987 A1 AR 082987A1 AR P110103347 A ARP110103347 A AR P110103347A AR P110103347 A ARP110103347 A AR P110103347A AR 082987 A1 AR082987 A1 AR 082987A1
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AR
Argentina
Prior art keywords
alkyl
amino
haloalkyl
haloc
sulfonyl
Prior art date
Application number
ARP110103347A
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English (en)
Inventor
Simon Maechling
Michael Maue
Arnd Voerste
Tetsuya Murata
Mamoru Hatazawa
Peter Bruechner
Reiner Fischer
Johannes-Rudolf Jansen
Tobias Kapferer
Hidekazu Watanabe
Jun Mihara
Hidetoshi Kishikawa
Daiei Yamazaki
Katsuhiko Shibuya
Koichi Araki
Eiichi Shimojo
Teruyuki Ichihara
Tadashi Ishikawa
Original Assignee
Bayer Cropscience Ag
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Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of AR082987A1 publication Critical patent/AR082987A1/es

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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • 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
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    • 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
    • A01N43/48—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
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
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    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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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    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
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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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
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    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
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  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Los compuestos se usan como pesticidas y agentes para controlar parásitos animales y de la agricultura, la horticultura y la silvicultura. Dichos parásitos son, entre otros los insectos, nematodos, helmintos y moluscos.Reivindicación 1: Arilpirrolidinas de fórmula (1) en la que R1 es alquilo C1-12, cicloalquilo C3-8, haloalquilo C1-12, halocicloalquilo C3-8; R2 es oxo y/o tioxo y n es 1 ó 2, si la línea discontinua en la fórmula (1) representa un enlace, de modo que R2 está unido a través de un enlace doble o sencillo al anillo de pirrolidina; o R2 es independientemente halógeno, nitro, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, alcoxi C1-12, haloalcoxi C1-12, (alquil C1-12)sulfenilo, (alquil C1-12)sulfinilo, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfenilo, (haloalquil C1-12)sulfinilo, (haloalquil C1-12)sulfonilo, pentafluoruro de azufre, alcoxi C1-12-carbonilo, haloalcoxi C1-12-carbonilo, alcoxi C1-12-carboniloxi o haloalcoxi C1-12-carboniloxi, n es 1 ó 2, si la línea discontinua en la fórmula (1) no representa nada, de modo que R2 está unido a través de un enlace sencillo al anillo de pirrolidina; A es C-X3 o nitrógeno; X1, X2, X3 y X4 es cada uno independientemente hidrógeno, halógeno, nitro, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, alcoxi C1-12, haloalcoxi C1-12, (alquil C1-12)sulfenilo, (alquil C1-12)sulfinilo, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfenilo, (haloalquil C1-12)sulfinilo, (haloalquil C1-12)sulfonilo, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12)(haloalquil C1-12)amino o pentafluoruro de azufre; B1 es C-Y1 o nitrógeno; B2 es C-Y2 o nitrógeno; B3 es C-Y3 o nitrógeno; B4 es C-Y4 o nitrógeno; B3, B4 y un enlace entre B3 y B4 representan juntos azufre; Y1, Y2, Y3, y Y4 es cada uno independientemente hidrógeno, halógeno, nitro, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, cicloalquilo C3-8, halocicloalquilo C3-8, alcoxi C1-12, haloalcoxi C1-12, (alquil C1-12)sulfenilo, (alquil C1-12)sulfinilo, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfenilo, (haloalquil C1-12)sulfinilo, (haloalquil C1-12)sulfonilo, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12)(haloalquil C1-12)amino, pentafluoruro de azufre, arilo o heterociclilo; o en la que en la fórmula (1) el resto químico de fórmula (a) significa unos de los restos químicos de fórmula (b) ó (g), en los que B4 y B3 son como se han definido antes; Y5 es hidrógeno, halógeno, nitro, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, cicloalquilo C3-8, halocicloalquilo C3-8, alcoxi C1-12, haloalcoxi C1-12, (alquil C1-12)sulfenilo, (alquil C1-12)sulfinilo, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfenilo, (haloalquil C1-12)sulfinilo, (haloalquil C1-12)sulfonilo, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12)(haloalquil C1-12)amino o pentafluoruro de azufre; y n’ es 1, 2, 3 ó 4; G es el resto químico de fórmula (d) ó (e) o es un grupo heterociclilo opcionalmente sustituido seleccionado de los compuestos de fórmula G1 a G9, en los que (Z) es hidrógeno, halógeno, nitro, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, alcoxi C1-12, haloalcoxi C1-12, (alquil C1-12)sulfenilo, (alquil C1-12)sulfinilo, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfenilo, (haloalquil C1-12)sulfinilo, (haloalquil C1-12)sulfonilo o pentafluoruro de azufre; y l es 1, 2 ó 3; R3 es hidrógeno, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, alquenilo C2-12, haloalquenilo C2-12, alquinilo C2-12, haloalquinilo C2-12, alquil C2-12-carbonilo, haloalquil C2-12-carbonilo, alcoxi C2-12-carbonilo o haloalcoxi C1-12-carbonilo, alcoxi C2-12-alquilo C1-12, o ciano-alquilo C1-12; R4 es hidrógeno, ciano, hidroxi, mercapto, amino, alquilo C1-12, haloalquilo C1-12, cicloalquilo C3-8, halocicloalquilo C3-8, cicloalquil C3-8-alquilo C1-12, halocicloalquil C3-8-alquilo C1-12, alquenilo C2-12, haloalquenilo C2-12, alquinilo C2-12, haloalquinilo C2-12, alcoxi C1-12, haloalcoxi C1-12, alcoxi C1-12-alquilo C1-12, haloalcoxi C1-12-alquilo C1-12, alquil C1-12-S-alquilo C1-12, haloalquil C1-12-S-alquilo C1-12, alquil C1-12-S(O)-alquilo C1-12, haloalquil C1-12-S(O)-alquilo C1-12, alquil C1-12-S(O)2-alquilo C1-12, haloalquil C1-12-S(O)2-alquilo C1-12, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfonilo, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12)(haloalquil C1-12)amino, cianoalquilo C1-12, ciano-cicloalquilo C3-8, arilo, aril-alquilo C1-12, un grupo heterocíclico, alquilo C1-12 sustituido con un grupo heterocíclico, alquil C1-12-O-N=CH-, haloalquil C1-12-O-N=CH- o (R8)(R9)N-CO-alquilo C1-12; R5 y R6 es cada uno independientemente hidrógeno, ciano, alquilo C1-12, haloalquilo C1-12, cicloalquilo C3-8, halocicloalquilo C3-8, alcoxi C1-12-carbonilo o haloalcoxi C1-12-carbonilo; R7 es hidrógeno, o alquilo C1-12 opcionalmente sustituido, cianoalquilo C1-12 y haloalquilo C1-12, o cicloalquilo C3-8 opcionalmente sustituido, halocicloalquilo C3-8, cicloalquil C3-8-alquilo C1-12, y halocicloalquil C3-8-alquilo C1-12, alquenilo C2-12, haloalquenilo C2-12, alquinilo C2-12, haloalquinilo C2-12, alcoxi C1-12, haloalcoxi C1-12, alcoxi C1-12-alquilo C1-12, haloalcoxi C1-12-alquilo C1-12, alquil C1-12-S-alquilo C1-12, haloalquil C1-12-S-alquilo C1-12, alquil C1-12-S(O)-alquilo C1-12, haloalquil C1-12-S(O)-alquilo C1-12, alquil C1-12-S(O)2-alquilo C1-12, haloalquil C1-12-S(O)2-alquilo C1-12, amino, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12)(haloalquil C1-12)amino, arilo opcionalmente sustituido y aril-alquilo C1-12, un grupo heterocíclico opcionalmente sustituido, alquilo C1-12 sustituido con un grupo heterocíclico, alquil C1-12-carbonilo, haloalquil C1-12-carbonilo o (R8)(R9)N-CO-; R8 y R9 es cada uno independientemente hidrógeno, ciano, hidroxi, amino, alquilo C1-12, haloalquilo C1-12, cicloalquilo C3-8, halocicloalquilo C3-8, cicloalquil C3-8-alquilo C1-12, halocicloalquil C3-8-alquilo C1-12, alquenilo C2-12, haloalquenilo C2-12, alquinilo C2-12, haloalquinilo C2-12, alcoxi C1-12, haloalcoxi C1-12, alcoxi C1-12-alquilo C1-12, haloalcoxi C1-12-alquilo C1-12, alquil C1-12-S-alquilo C1-12, haloalquil C1-12-S-alquilo C1-12, alquil C1-12-S(O)-alquilo C1-12, haloalquil C1-12-S(O)-alquilo C1-12, alquil C1-12-S(O)2-alquilo C1-12, haloalquil C1-12-S(O)2-alquilo C1-12, (alquil C1-12)sulfonilo, (haloalquil C1-12)sulfonilo, (alquil C1-12)amino, di(alquil C1-12)amino, (haloalquil C1-12)amino, di(haloalquil C1-12)amino, (alquil C1-12) (haloalquil C1-12)amino, ciano alquilo C1-12, ciano-cicloalquilo C3-8, arilo, aril-alquilo C1-12, un grupo heterocíclico o alquilo C1-12 sustituido con un grupo heterocíclico; W es oxígeno o azufre; m es 1 ó 2; y cuando B2 es C-Y2 entonces uno cualquiera de la pareja Y2 y R5 o la pareja Y2 y R6 puede formar, junto con los átomos de carbono a los que están unidos y además junto con el(los) átomo(s) de carbono entre dichos átomos de carbono, un anillo hidrocarbonato de 5 a 7 miembros, que puede ser no saturado; si en los compuestos de fórmula (1), G es el resto químico de fórmula (e), siendo m 1, siendo B2 C-Y2, entonces R5 y Y2 junto con los átomos de carbono a los que éstos están unidos junto con el resto químico de fórmula (a), pueden formar el resto químico cíclico de fórmula (k) en el que R6’ es hidrógeno o alquilo C1-6; E es oxígeno, azufre o un grupo alcano C1-3 diilo, grupo que puede estar opcionalmente sustituido con 1 ó 2 grupos alquilo C1-6; y B1, B3, B4, R3, y R7 son como se han definido antes.
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JP2012082186A (ja) 2012-04-26
JP2013538222A (ja) 2013-10-10
US20140046069A1 (en) 2014-02-13
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BR112013006293A2 (pt) 2017-09-26
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