AR052672A1 - Derivados de pirazina como fungicidas - Google Patents

Derivados de pirazina como fungicidas

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Publication number
AR052672A1
AR052672A1 ARP060100533A ARP060100533A AR052672A1 AR 052672 A1 AR052672 A1 AR 052672A1 AR P060100533 A ARP060100533 A AR P060100533A AR P060100533 A ARP060100533 A AR P060100533A AR 052672 A1 AR052672 A1 AR 052672A1
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AR
Argentina
Prior art keywords
alkyl
haloalkyl
cycloalkyl
ring
cyano
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ARP060100533A
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English (en)
Inventor
James F Bereznak
Paula L Sharpe
Thomas M Stevenson
Andrew E Taggi
Chi-Ping Tseng
Wenming Zhang
Sheth Ritesh Bharat
Original Assignee
Du Pont
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Publication of AR052672A1 publication Critical patent/AR052672A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/18—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/20—Nitrogen atoms
    • 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
    • C07D401/04—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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D403/04—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D403/14—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
    • 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
    • C07D405/04—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
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Derivados de pirazina, compuestos, sus N-oxidos y sales aceptables para su uso en agricultura, con utilidad como funguicidas. Composiciones que contienen los compuestos de formula (1) y un método para controlar enfermedades de plantas causadas por patogenos fungicos de plantas que involucra aplicar una cantidad efectiva de un compuesto de formula (1). Reivindicacion 1: Un compuesto caracterizado porque se selecciona entre la formula 1, un N-oxido o una sal aceptable para su uso en agricultura del mismo, donde R1 es NR4R5, N=CR19R21, OR6, G1 o G2, o C1-8 alquilo, C2-8 alquenilo, C3-8 alquinilo, C3-8 cicloalquilo, C3-8 cicloalquenilo, C4-8 cicloalquilalquilo, C4-8 alquilcicloalquilo, C4-8 cicloalquenilalquilo o C4-8 alquilcicloalquenilo, cada uno opcionalmente sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en halogeno, ciano, nitro, hidroxi, C1-4 alcoxi, C1-4 haloalcoxi, C1-4 alquiltio, C1-4 alquilamino, C1-4 alquilsulfinilo, C1-4 alquilsulfonilo, C2-6 alcoxicarbonilo, C2-6 alquilcarbonilo, C3-6 trialquilsililo, G1 y G2; A es O, S o NR7; R7 es H, C1-4 alquilo, C1-4 haloalquilo, C2-6 alquilcarbonilo o C2-6 alcoxicarbonilo; R2 es ciano, NR8-N=CR9R10, O-N=CR9R10, NR8- NR11R12, O-NR11R12, CR13=NOR14, CR13=NNR11R12, C(W) NR22R23, NC(=O)R30, NC(=O)NR31 o NC(=O)OR32; o R2 es un anillo heteroaromático de 5 o 6 miembros o un sistema de anillos bicíclico heteroaromático de 8, 9 o 10 miembros, donde cada anillo o sistema de anillos está opcionalmente sustituido con hasta 5 sustituyentes seleccionados entre R24; o anillo heterocíclico saturado o parcialmente de 5 o 6 miembros, incluyendo opcionalmente entre 1 y 3 miembros del anillo seleccionados entre el grupo que consiste en C(=O), C(=S), S(O), o S(O)2, opcionalmente sustituido con hasta 5 sustituyentes seleccionados entre R24; W es O, S o =NR25; R3 es H, halogeno, ciano, C1-6 alquilo, C1-4 haloalquilo, C3-6 cicloalquilo, C3-6 halocicloalquilo, C2-6 alquenilo, C3-6 alquinilo, C1-4 alcoxi, C1-4 haloalcoxi, C1-4 alquiltio, C1-4 haloalquiltio, C2-5 alcoxicarbonilo, hidroxicarbonilo, -SCN o -CHO; cada uno de R4 y R5 es en forma independiente H, o C1-8 alquilo, C3-8 alquenilo, C3-8 alquinilo, C3-8 cicloalquilo, C3-8 cicloalquenilo, C4-8 cicloalquilalquilo o C4-8 cicloalquenilalquilo, cada uno opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados entre halogeno, ciano, C1-6 alcoxi, C1-6 tioalquilo, C2-6 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 dialquilamino, -SCN y C3-6 trialquilsililo; o R4 y R5 se toman juntos como -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -CH2CH2OCH2CH2- o CH2CH(CH3)OCH(CH3)CH2-; R6 es H, o C1-8 alquilo, C3-8 alquenilo, C3-8 alquinilo, C3-8 cicloalquilo, C3-8 cicloalquenilo, C4-8 cicloalquilalquilo o C4-8 cicloalquenilalquilo, cada uno opcionalmente sustituido con 1 y 4 sustituyentes seleccionados entre halogeno, ciano, C1-6 alcoxi, C1-6 tioalquilo, C2-6 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 dialquilamino, -SCN y C3-6 trialquilsililo; R8 es H, C1-4 alquilo o C1-4 haloalquilo; R9 es C1-4 alquilo o C1-4 haloalquilo; R10 es H, C1-4 alquilo o C1-4 haloalquilo; o R9 y R10 se toman juntos como -(CH2)3-, -(CH2)4-, -(CH2)5- o -(CH2)6-; R11 es H, C1-4 alquilo o C1-4 haloalquilo; R12 es H, C1-4 alquilo o C1-4 haloalquilo, C2-3 alquilcarbonilo o C2-3 alcoxicarbonilo; o R11 y R12 se toman juntos como -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- o CH2CH(CH3) OCH(CH3)CH2-; R13 es H, NH2, C1-4 alquilo o C1-4 haloalquilo; R14 es H, C1-4 alquilo o C1-4 haloalquilo; J es C1-8 alquilo, C2-8 alquenilo, C3-8 alquinilo, C3-8 cicloalquilo, C3-8 cicloalquenilo, C4-8 cicloalquilalquilo, C4-8 alquilcicloalquilo, C4-8 cicloalquenilalquilo o C4-8 alquilcicloalquenilo, cada uno opcionalmente sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en halogeno, ciano, nitro, hidroxi, C1-4 alcoxi, C1-4 haloalcoxi, C1-4 alquiltio, C1-4 alquilsulfinilo, C1-4 alquilsulfonilo, C2-6 alcoxicarbonilo, C2-6 alquilcarbonilo, C3-6 trialquilsililo y C1-4 alquilamino; o J es un anillo heteroaromático de 5 o 6 miembros o un sistema de anillos bicíclico heteroaromático de 8, 9 o 10 miembros fenilo, bencilo, naftaleno, donde cada anillo o sistema de anillos está opcionalmente sustituido con hasta 5 sustituyentes seleccionados entre halogeno, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, C1-6 haloalquilo, C2-6 haloalquenilo, ciano, nitro, C1-6 alcoxi, C1-6 haloalcoxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 haloalquiltio, C1-6 haloalquilsulfinilo, C1-6 haloalquilsulfonilo, C1-6 alquilamino, C2-6 dialquilamino, C2-6 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 alquilaminocarbonilo, C3-6 dialquilaminocarbonilo y C3-6 trialquilsililo; G1 es un anillo carbocíclico o heterocíclico no aromático de entre 3 y 7 miembros, que incluye opcionalmente 1 o 2 miembros del anillo seleccionados entre el grupo que consiste en C(=O), C(=S), S(O) y S(O)2 y opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados entre R17; G2 es un anillo fenilo, anillo heteroaromático de 5 o 6 miembros, donde cada anillo o sistema de anillos está opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados en forma independiente entre R18; cada R17 es en forma independiente C1-2 alquilo, C1-2 haloalquilo, halogeno, ciano, nitro o C1-2 alcoxi; cada R18 es en forma independiente C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C3-6 cicloalquilo, C1-4 haloalquilo, C2-4 haloalquenilo, C2-4 haloalquinilo, C3-6 halocicloalquilo, halogeno, ciano, nitro, C1-4 alcoxi, C1-4 haloalcoxi, C1-4 alquiltio, C1-4 alquilsulfinilo, C1-4 alquilsulfonilo, C1-4 alquilamino, C2-8 dialquilamino, C3-6 cicloalquilamino, (C1-4 alquil)(C3-6 cicloalquil)amino, C2-4 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 alquilaminocarbonilo, C3-8 dialquilaminocarbonilo o C3-8 trialquilsililo; cada R19 y R21 es en forma independiente H, C1-4 alquilo, C1-4 haloalquilo o C3-8 cicloalquilo; o R19 y R21 se toman juntos como -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- o CH2CH(CH3)OCH(CH3)CH2-; cada R22 y R23 es en forma independiente H, C1-4 alquilo, C3-8 cicloalquilo, C4-8 cicloalquilalquilo cada uno opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados entre halogeno, ciano, alcoxi C1-6, C1-6 tioalquilo, C2-6 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 dialquilamino, -SCN y C3-6 trialquilsililo; o R22 y R23 se toman juntos como -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- o CH2CH(CH3)OCH(CH3)CH2-;cada R24 es en forma independiente halogeno, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, C1-6 haloalquilo, C2-6 alcoxialquilo, C3-6 dialcoxialquilo, C2-6 haloalquenilo, ciano, nitro, C1-6 alcoxi, C1-6 haloalcoxi, C1-6 alquiltio, C1-6 alquilsulfinilo, C1-6 alquilsulfonilo, C1-6 haloalquiltio, C1-6 haloalquilsulfinilo, C1-6 haloalquilsulfonilo, C1-6 alquilamino, C2-6 dialquilamino, C2-6 alquilcarbonilo, C2-6 alcoxicarbonilo, C2-6 alquilaminocarbonilo, C3-6 dialquilaminocarbonilo o C3-6 trialquilsililo; y R25 es H, C1-4 alquilo o C1-4 haloalquilo; R30 es H, C1-6 alquilo, C1-4 haloalquilo, C3-6 cicloalquilo, C3-6 halocicloalquilo, C2-6 alquenilo o C3-6 alquinilo; o anillo fenilo, anillo heteroaromático de 5 o 6 miembros, donde cada anillo o sistema de anillos está opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C3-6 cicloalquilo, C1-4 haloalquilo, C2-4 haloalquenilo, C2-4 haloalquinilo, C3-6 halocicloalquilo, halogeno, ciano, nitro, C1-4 alcoxi y C1-4 haloalcoxi, y cada R31 y R32 es en forma independiente C1-6 alquilo, C1-4 haloalquilo, C3-6 cicloalquilo, C3-6 halocicloalquilo, C2-6 alquenilo o C3-6 alquinilo; o anillo fenilo, opcionalmente sustituido con entre 1 y 4 sustituyentes seleccionados en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C3-6 cicloalquilo, C1-4 haloalquilo, C2-4 halogeno, ciano, nitro, C1-4 alcoxi y C1-4 haloalcoxi, con la condicion de que cuando R2 es NR8-N= CR9R10, O-N=CR9R10, NR8-NR11R12, O-NR11R12, CR13=NOR14 o CR13=NNR11R12, entonces J es fenilo sustituido con al menos un sustituyente seleccionado entre halogeno y metilo.
ARP060100533A 2005-02-15 2006-02-15 Derivados de pirazina como fungicidas AR052672A1 (es)

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EP (1) EP1848711A1 (es)
JP (1) JP2008530231A (es)
AR (1) AR052672A1 (es)
CA (1) CA2598897A1 (es)
GT (1) GT200600061A (es)
TW (1) TW200640881A (es)
WO (1) WO2006089060A1 (es)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2034993A2 (en) * 2006-06-21 2009-03-18 E.I. Du Pont De Nemours And Company Pyrazinones as cellular proliferation inhibitors
WO2008107398A2 (en) * 2007-03-02 2008-09-12 Basf Se Pyrazine compounds
BRPI0910833A2 (pt) * 2008-04-29 2015-08-11 Merck Patent Ges Mit Beschränkter Hatfung Derivado de arilpirazinona como estimuladores da secreção de insulina, métodos para obtenção dos mesmos e uso dos mesmos para o tratamento de diabetes
JP6002034B2 (ja) * 2009-05-06 2016-10-05 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 病原体圧の本質的に非存在下で農作物の活力および／または作物収穫量を増加させる方法
TW201247631A (en) 2011-04-28 2012-12-01 Du Pont Herbicidal pyrazinones
WO2018225816A1 (ja) * 2017-06-07 2018-12-13 三井化学アグロ株式会社 含窒素複素環化合物ならびにそれを有効成分とする農園芸用殺菌剤

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CZ65398A3 (cs) * 1995-09-22 1998-07-15 Sumitomo Chemical Company, Limited Derivát pyrazinu-2-on, způsob kontroly nechtěných plevelů a použití derivátu
JP4199309B2 (ja) * 1996-09-06 2008-12-17 日本化薬株式会社 新規アセトアミド誘導体およびプロテアーゼ阻害
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
US6664255B1 (en) * 1999-05-19 2003-12-16 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
SK13752003A3 (en) * 2001-05-14 2004-11-03 Bristol Myers Squibb Pharma Co Substituted pyrazinones, pyridines and pyrimidines as ligands of factor releasing corticotropine
CN1312134C (zh) * 2001-11-19 2007-04-25 巴斯福股份公司 5－苯基嘧啶化合物、包含它们的组合物、其制备方法及其用途
TW200500341A (en) * 2002-11-12 2005-01-01 Astrazeneca Ab Novel compounds

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EP1848711A1 (en) 2007-10-31
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GT200600061A (es) 2006-10-18
CA2598897A1 (en) 2006-08-24
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