AR088581A1 - 4-ciano-3-fenil-4-(piridin-3-il)butanoatos sustituidos, procedimientos para su preparacion y su uso como herbicidas y reguladores del crecimiento de las plantas - Google Patents

4-ciano-3-fenil-4-(piridin-3-il)butanoatos sustituidos, procedimientos para su preparacion y su uso como herbicidas y reguladores del crecimiento de las plantas

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Publication number
AR088581A1
AR088581A1 ARP120104058A ARP120104058A AR088581A1 AR 088581 A1 AR088581 A1 AR 088581A1 AR P120104058 A ARP120104058 A AR P120104058A AR P120104058 A ARP120104058 A AR P120104058A AR 088581 A1 AR088581 A1 AR 088581A1
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Argentina
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alkyl
substituted
group
halogen
haloalkoxy
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Dr Jakobi Harald
Dr Mosrin Marc
Dr Dietrich Hansjrg
Dr Gatzweiler Elmar
Dr Huser-Hahn Isolde
Dr Heinemann Ines
Hugh Dr Rosinger Christopher
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Bayer Intellectual Property GmbH
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Bayer Intellectual Property GmbH
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    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro 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
    • 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
    • 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
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

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

Abstract

Son adecuados como herbicidas para el control de plantas perjudiciales o como reguladores del crecimiento de las plantas. Reivindicación 1: Compuestos de la fórmula (1) o sus sales, en la que (R¹)ₘ significa m sustituyentes R¹, donde R¹, cuando m = 1, o cada uno de los sustituyentes R¹, cuando m es mayor que 1, independientemente entre sí, significa halógeno, ciano, nitro, hidroxi, alquilo C₁₋₈, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₈, alquiltio C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, haloalquiltio C₁₋₆, haloalquilsulfinilo C₁₋₆, haloalquilsulfonilo C₁₋₆, haloalquenilo C₂₋₆, haloalquinilo C₂₋₆, alcoxi C₁₋₆-alquilo C₁₋₄, haloalcoxi C₁₋₆-alquilo C₁₋₄, cicloalquilo C₃₋₆, que, dado el caso, está sustituido con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, cicloalcoxi C₃₋₆, que, dado el caso, está sustituido con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, o un resto de la fórmula C(O)OR⁵, C(O)NR⁶R⁷, C(O)-Het¹, NR⁸R⁹ o Het², o significan en cada caso dos grupos R¹ que se encuentran en posición orto en el anillo o R¹ y R³ juntos un grupo de la fórmula Z¹-A*-Z², en la que A* representa un grupo alquileno con 1 a 4 átomos de C, que dado el caso, está sustituido con uno o varios restos del grupo de halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ y haloalcoxi C₁₋₄, Z¹ representa un enlace directo, O ó S y Z² representa un enlace directo, O ó S, formando el grupo Z¹-A*-Z² junto con los átomos de C del anillo de fenilo unidos al grupo un anillo de 5 ó 6 miembros condensado; (R²)ₙ significa n sustituyentes R², donde R², cuando n = 1, o cada uno de los sustituyentes R², cuando n es mayor de 1, independientemente entre sí significa halógeno, ciano, nitro, hidroxi, alquilo C₁₋₈, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₈, alquiltio C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, haloalquiltio C₁₋₆, haloalquilsulfinilo C₁₋₆, haloalquilsulfonilo C₁₋₆, haloalquenilo C₂₋₆, haloalquinilo C₂₋₆, alcoxi C₁₋₆-alquilo C₁₋₄, haloalcoxi C₁₋₆-alquilo C₁₋₄, cicloalquilo C₃₋₆, que dado el caso, están sustituidos con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, cicloalcoxi C₃₋₆, que dado el caso, está sustituido con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, o un resto de la fórmula C(O)OR¹⁰, C(O)NR¹¹R¹², C(O)-Het³, NR¹³R¹⁴ o Het⁴, o significando en cada caso dos grupos R² que se encuentran en posición orto en el anillo juntos un grupo de la fórmula Z³-A**-Z⁴, en la que A** representa un grupo alquileno con 1 a 4 átomos de C, que dado el caso, está sustituido con uno o varios restos del grupo de halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ y haloalcoxi C₁₋₄, Z³ representa un enlace directo, O ó S y Z⁴ representa un enlace directo, O ó S, formando el grupo Z³-A**-Z⁴ conjuntamente con los átomos de C del anillo de fenilo unidos al grupo un anillo de 5 ó 6 miembros condensado; R³ significa halógeno, ciano, nitro, hidroxi, alquilo C₁₋₈, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₈, alquiltio C₁₋₈, alquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, haloalquiltio C₁₋₆, haloalquilsulfinilo C₁₋₆, haloalquilsulfonilo C₁₋₆, haloalquenilo C₂₋₆, haloalquinilo C₂₋₆, alcoxi C₁₋₆- alquilo C₁₋₄, haloalcoxi C₁₋₆-alquilo C₁₋₄, cicloalquilo C₃₋₆, que dado el caso está sustituido con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, cicloalcoxi C₃₋₆, que dado el caso está sustituido con uno o varios restos del grupo de halógeno y alquilo C₁₋₄, o un resto de la fórmula C(O)OR¹⁵, C(O)NR¹⁶R¹⁷, C(O)-Het⁵, NR¹⁸R¹⁹ o Het⁶; R⁴ significa hidrógeno o un resto hidrolizable, preferentemente R⁴ hidrógeno o un resto hidrocarburo dado el caso sustituido o un resto heterociclilo dado el caso sustituido, significando cada uno de los dos restos que contienen carbono mencionados en último lugar inclusive los sustituyentes 1 a 30 átomos de C, preferentemente 1 a 24 átomos de C, en especial 1 a 20 átomos de C, o R⁴ significa un resto de la fórmula SiRᵃRᵇRᶜ, -NRᵃRᵇ o N=CRᶜRᵈ, donde en las 3 fórmulas mencionadas en último lugar cada uno de los restos Rᵃ, Rᵇ, Rᶜ y Rᵈ independientemente entre sí significan hidrógeno o un resto hidrocarburo dado el caso sustituido, pero SiH₃ está excluido para SiRᵃRᵇRᶜ, o Rᵃ y Rᵇ junto con el átomo de N del grupo NRᵃRᵇ significan un heterociclo de 3 a 9 miembros, que puede contener adicionalmente al átomo de N uno o dos heteroátomos del anillo adicionales del grupo de N, O y S, y que está sin sustituir o sustituido, o Rᶜ y Rᵈ junto con el átomo de C del grupo N =CRᶜRᵈ significan un resto carbocíclico de 3 a 9 miembros o un resto heterocíclico, que puede contener de 1 a 3 heteroátomos del anillo del grupo de N, O y S, estando sin sustituir o sustituido el resto carbocíclico o heterocíclico, presentando cada uno de los restos Rᵃ, Rᵇ, Rᶜ y Rᵈ inclusive sustituyentes hasta 30 átomos de C, preferentemente hasta 24 átomos de C, en especial hasta 20 átomos de C, o R⁴ significa un resto de la fórmula -C(=O)Rᵉ o -P(=O)(Rᶠ)₂, donde Rᵉ y los Rᶠ independientemente entre sí respectivamente significan hidrógeno, OH, alquilo C₁₋₈, haloalquilo C₁₋₄, alquenilo C₂₋₈, alquinilo C₂₋₈, alcoxi C₁₋₆, alcoxi-C₁₋₆-alquilo C₁₋₈, haloalcoxi C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₈, alqueniloxi C₃₋₈, alqueniloxi C₃₋₈-alquilo C₁₋₈, alquiniloxi C₃₋₈, alquiniloxi C₃₋₈-alquilo C₁₋₈, NR*R**, estando R* y R** definidos más adelante, tri-[alquil C₁₋₄]-sililo, tri-[alquil C₁₋₄]-silil-alquilo C₁₋₈, cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₈, cicloalquenilo C₅₋₆, cicloalquenil C₅₋₆-alquilo C₁₋₈, cicloalquinilo C₅₋₆, cicloalquinil C₅₋₆-alquilo C₁₋₈, fenilo, fenil-alquilo C₁₋₈, fenoxi, fenoxi-alquilo C₁₋₈, fenilamino, fenilamin-alquilo C₁₋₈, un resto Het⁷, Het⁷-alquilo C₁₋₆ o Het⁷-O-alquilo C₁₋₆, estando cada uno de los 15 restos mencionados en último lugar en la parte acíclica sin sustituir o sustituidos con uno o varios restos de RA iguales o diferentes y en la parte cíclica sin sustituir o sustituidos con uno varios restos de RB iguales o diferentes; R⁵, R¹⁰ y R¹⁵ en cada caso significan independientemente entre sí hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₄, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄ o los grupos M mencionados más adelante significan preferentemente alquilo C₁₋₄; R⁶, R⁷, R⁸, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸ y R¹⁹ en cada caso significan, independientemente entre sí, hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆ o alquinilo C₂₋₆, estando cada uno de los 3 restos mencionados en último lugar en cada caso independientemente entre sí sin sustituir o sustituidos con uno o varios restos del grupo de halógeno, nitro, ciano y fenilo, que dado el caso está sustituido, preferentemente sin sustituir o sustituido con uno o varios restos del grupo de halógeno, nitro, ciano, alquilo C₁₋₄ y haloalquilo C₁₋₄, o cicloalquilo C₃₋₆ o fenilo, estando cada uno de los 2 restos menc
ARP120104058A 2011-10-31 2012-10-30 4-ciano-3-fenil-4-(piridin-3-il)butanoatos sustituidos, procedimientos para su preparacion y su uso como herbicidas y reguladores del crecimiento de las plantas Pending AR088581A1 (es)

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US (1) US8975412B2 (es)
EP (1) EP2773614B1 (es)
JP (1) JP5952909B2 (es)
KR (1) KR20140084204A (es)
CN (1) CN103889954B (es)
AR (1) AR088581A1 (es)
AU (1) AU2012331286A1 (es)
BR (1) BR112014010366B1 (es)
CA (1) CA2853579A1 (es)
EA (1) EA025426B1 (es)
IN (1) IN2014CN03169A (es)
MX (1) MX2014004779A (es)
WO (1) WO2013064462A1 (es)

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BR112015013816A2 (pt) * 2012-12-21 2017-07-11 Bayer Cropscience Ag 4-ciano-3-(piridil)-4-fenilbutanoatos substituídos, processos para sua preparação e seu uso como herbicidas e reguladores do crescimento da planta
EP3164387A1 (de) * 2014-07-04 2017-05-10 Bayer CropScience Aktiengesellschaft Substituierte 5-hydroxy-2-heteroaryl-3-phenylpentanonitrilderivate, verfahren zu deren herstellung und deren verwendung als herbizide und/oder pflanzenwachstumsregulatoren

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WO2013064462A1 (de) 2013-05-10
US20140296073A1 (en) 2014-10-02
JP2014532634A (ja) 2014-12-08
MX2014004779A (es) 2014-05-27
CN103889954A (zh) 2014-06-25
KR20140084204A (ko) 2014-07-04
EP2773614B1 (de) 2016-11-30
CA2853579A1 (en) 2013-05-10
EA201400519A1 (ru) 2014-10-30
EP2773614A1 (de) 2014-09-10
BR112014010366B1 (pt) 2018-11-21
AU2012331286A1 (en) 2014-05-22
BR112014010366A2 (pt) 2017-04-25
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CN103889954B (zh) 2016-12-07

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