DK2785708T3 - Insekticide triazinonderivater - Google Patents

Insekticide triazinonderivater Download PDF

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DK2785708T3
DK2785708T3 DK12787459.2T DK12787459T DK2785708T3 DK 2785708 T3 DK2785708 T3 DK 2785708T3 DK 12787459 T DK12787459 T DK 12787459T DK 2785708 T3 DK2785708 T3 DK 2785708T3
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Sebastian Rendler
Jürgen Harry Schaetzer
Shuji Hachisu
Peter Maienfisch
Thomas Pitterna
Olivier Jacop
Jérome Yves Cassayre
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Syngenta Participations Ag
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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
    • 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
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/14—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
    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • 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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  • Agricultural Chemicals And Associated Chemicals (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (19)

1. Forbindelser med formel I eller I':
(I) . <0 hvor R2 er hydrogen, formyl, Ci-C6alkyl, Ci-C3haloalkyl, Ci-C3alkoxy, Ci-C3haloalkoxy, Ci-C6alkoxyCi-C3alkyl, Ci-C6alkoxyCi-C3alkoxyCi-C3alkyl, C2-C6alkynyl, Ci-C4cyanoalkyl, C2-C6alkenyl, phenylCi-C4alkyl, Ci-C6alkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cgalkoxycarbonyl, Ci-C4alkoxycarbonylCi-C4alkyl, phenylCi- Csalkylcarbonyl, phenylCi-Csalkoxycarbonyl, heteroarylcarbonyl, phenylcarbonyl, Ci-C6alkylsulfonyl, phenylsulfonyl, C3- Cecycloalkylcarbonyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkoxycarbonyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkylCi-C4alkylcarbonyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, Ci-C6alkoxyCi-C6alkoxycarbonyl, Y er N eller C-R3, hvor R3 er hydrogen, hydroxy, Ci-C4alkoxy, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkylCi-C4alkyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, halogen, cyano eller nitro, Ci-C3haloalkylthio, C3- C3haloalkylsulfenyl, Ci-C3haloalkylsulfonyl eller Ci~ C3haloalkoxy; W er C-H eller N; n er 0 eller 1; Z er -N=CH- eller -NR4-CH2-, hvor R4 er hydrogen, formyl, Ci-Cealkyl, Ci-C6alkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci- Cealkoxycarbonyl, C2-C6alkenyloxycarbonyl, C2-C6alkynyl, C2- Cgalkenyl eller phenylCi-Csalkyloxycarbonyl; R1 er en hvilken som helst af Q1, Q2 eller Q3
(Q1) (Q2) (Q3) hvor X er 0, S eller NR5, hvor R5 er hydrogen, Ci-C6alkyl, C4-Cghaloalkyl, A1 er hydrogen, Ci-C6alkyl, Ci-C3haloalkyl, C2-C6alkynyl, CR-C4cyanoalkyl, C2-C6alkenyl, phenylCi-C4alkyl, heteroarylCR- C4alkyl, phenyl, heteroaryl, Ci-C6alkylcarbonyl, CR-C6haloalkylcarbonyl, Ci-C6alkoxycarbonyl, phenylCR- C5alkylcarbonyl, phenylcarbonyl, Ci-C6alkylsulfonyl, phenylsulfonyl, C3-C6cycloalkyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, CR-CgcycloalkylCR-C4alkyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkylcarbonyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, eller C3-C6cycloalkylCi-C4alkylcarbonyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S; A2 er hydrogen, Ci-C6alkyl, Ci-C3haloalkyl, C2-C6alkynyl, CR-C4cyanoalkyl, C2-C6alkenyl, phenylCi-C4alkyl, heteroarylCR- C4alkyl, phenyl, heteroaryl, C3-C6cycloalkyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkylCi-C4alkyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, CR-Cgalkylamino, CR-Cgdialkylamino, CR-Cgalkyloxy, hydroxy, amino; B1 er CR6R7 eller C (0) , S(0)m, hvor m er 1 eller 2; B2 er CR8R9, 0, NR10, hvor R10 er hydrogen, C4-C6alkyl eller CR-Cghaloalkyl; C1 er CRnR12, C (0) ; C2 er CR13R14; C3 er CR15R16, 0, NR17; hvor R17 er hydrogen, Ci-C6alkyl eller CR-Cghaloalkyl, hvor R6, R7, R8, R9, R1:i,R12, R13, R14, R15 og R16 hver uafhængigt af hinanden er hydrogen, Ci-C6alkyl, CR-CRhaloalkyl, phenyl, heteroaryl, C3-C6cycloalkyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, C3-C6cycloalkyl(C4- C4)alkyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, eller hvor R6, R7, R8, R9, R11, R12, R13, R14, R15 og R16 danner en 3-6-leddet carbonring, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, hvor phenyl- og heteroarylgrupperne ovenfor uafhængigt af hinanden eventuelt kan være substitueret med Ci-C3alkyl, Ci-Cahaloalkyl, Ci-C3alkoxy, Ci-C3haloalkoxy, Ci-C3alkylthio, Ci-Csalkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller med nitro, eller en tautomer deraf i hvert tilfælde i en fri form eller i saltform.
2. Forbindelse ifølge krav 1, hvor R2 er hydrogen, Ci~ C6alkylcarbonyl, Ci-C6alkoxycarbonyl, formyl, phenylCi- Csalkylcarbonyl, phenylCi-Csalkoxycarbonyl, phenylcarbonyl, C3-Cecycloalkylcarbonyl, Ci-C6alkoxyCi-C6alkoxycarbonyl, fortrinsvis hydrogen, Ci-C6alkylcarbonyl, Ci-C6alkoxycarbonyl eller formyl og mest fortrinsvis hydrogen, hvor phenylgrupperne ovenfor uafhængigt af hinanden eventuelt kan være substitueret med Ci-C3alkyl, Ci-C3haloalkyl, Ci-C3alkoxy, Ci-C3haloalkoxy, Ci-C3alkylthio, Ci~C3alkylsulfinyl, Ci- Csalkylsulfonyl, halogen, cyano eller med nitro.
3. Forbindelse ifølge krav 1, hvor Y er C-H, C-F, N, C-CF3, C-Cl, C-CH3, C-cyclo-Pr eller C-CN, fortrinsvis C-H, C-F, N, C-CF3 eller C-CN og mest fortrinsvis C-F, C-H eller N.
4. Forbindelse ifølge krav 1, hvor W er C-H.
5. Forbindelse ifølge krav 1, hvor n er 0.
6. Forbindelse ifølge krav 1, hvor Z er -N=CH- eller -NH-CH2- og mest fortrinsvis -N=CH-.
7. Forbindelse ifølge krav 1, hvor R1 er Q1, X er 0, N-CH3 eller N-H og fortrinsvis 0, A1 er hydrogen, Ci-C6alkyl, Ci-C3haloalkyl, C2-C6alkynyl, C2- Cealkenyl, phenylCi-C4alkyl, heteroarylCi-C4alkyl, C3- Cecycloalkyl, hvor en ringmethylengruppe eventuelt kan være erstattet med 0 eller S, eller C3-C6cycloalkylCi-C4alkyl, hvor en ring- eller kædemethylengruppe eventuelt kan være erstattet med 0 eller S, og fortrinsvis hydrogen, Ci-C6alkyl, C4-Cshaloalkyl og mest fortrinsvis Ci-C6alkyl eller Ci-C3haloalkyl, og A2 er hydrogen, Ci-C6alkyl, Ci-C3haloalkyl, phenyl, heteroaryl eller C3-C6cycloalkyl og fortrinsvis hydrogen, Ci-C6alkyl, C4-Cshaloalkyl eller cyclopropyl og mest fortrinsvis hydrogen eller Ci-C4alkyl, hvor phenyl- og heteroarylgrupperne ovenfor uafhængigt af hinanden eventuelt kan være substitueret med C4-C3alkyl, Ci-C3haloalkyl, Ci~C3alkoxy, Ci-C3haloalkoxy, C4-Csalkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller med nitro
8. Forbindelse ifølge krav 1, hvor R1 er Q2, X fortrinsvis er 0, N-CH3 eller N-H og mest fortrinsvis 0, B1 er CH2, CH(CH3), CH(CF3), C (CF3) (CH3) , C(CH3)2, C(CF3)2, C(CH2)2, S (0)2, C(aryl) (H) eller C(aryl) (CH3) og fortrinsvis C(CH3)2, C(CF3)2 eller CH(CH3) og mest fortrinsvis C(CH3)2 eller C (CF3) 2, og B2 er 0, NH, N(CH3) eller CH2 og fortrinsvis 0 eller CH2 og mest fortrinsvis CH2.
9. Forbindelse ifølge krav 1, hvor R1 er Q3, X fortrinsvis er 0, N-CH3 eller N-H og mest fortrinsvis 0, C er CH2, C (0) , CH(CH3), C(CH3)2 eller C(CH2)2 og fortrinsvis C(0) eller CH2 og mest fortrinsvis CH2, C er CH2, CH(CH3), C(CH3)2 eller C(CH2)2 og mest fortrinsvis CH2 eller C(CH3)2 og mest fortrinsvis CH2, og C er CH2, NH, N(CH3) eller 0 og mest fortrinsvis CH2 eller 0 og mest fortrinsvis 0.
10. Forbindelse ifølge krav 1, hvor: R2 er H, C(0)CH3, C(0)0t-Bu, C(0)0CH2Ph, C(0)0Et, C (0) 0 (CH2) 2OCH3, C (0) isobutyl, C (0) isopropyl eller C(0)cyclo-Pr og fortrinsvis H, - Y er C-H, C-F, C-Cl, C-Br, C-CH3, C-CF3, C-cyclo-Pr, C-C=N, C-CH=CH2 eller N og fortrinsvis C-H, C-F eller N, - W er C-H eller N, - n er 0 eller 1 og fortrinsvis 0, - Z er N=CH eller NH-CH2, - R1 er Q1 med X er O, N-Me eller NH og fortrinsvis O, A1 er H, CH3, ethyl, CH2CF3, tert-butyl, 3,5-Cl2C6H3, CH2-2, 6-Cl2C6H3 og fortrinsvis H, CH3, ethyl, A2 er H, CH3, ethyl, CF3, t-C4H9, 3,5-Cl2C6H3, fortrinsvis H eller CH3.
11. Forbindelse ifølge krav 1, hvor: R2 er H, C(0)CH3, C(0)0t-Bu, C(0)0CH2Ph, C(0)0Et, C (O) O (CH2) 2OCH3, C (O) isobutyl, C (O) isopropyl eller C (O) cyclo-Pr og fortrinsvis H, - Y er C-H, C-F, C-Cl, C-Br, C-CH3, C-CF3, C-cyclo-Pr, C-C=N, C-CH=CH2 eller N og fortrinsvis C-H, C-F eller N, - W er C-H eller N, - n er 0 eller 1 og fortrinsvis 0, - Z er N=CH eller NH-CH2, - R1 er Q2 med X er O, N-Me eller NH og fortrinsvis O, B1 er CMe2, CHMe, C(CF3)Me, C(CF3)2, CH(CF3), CH (3, 5-Cl2C6H3) , CH(2,6-C12C6H3) , C (CF3) (3,5-Cl2C6H3) , C(CH2)2 og fortrinsvis CMe2 eller C(CF3)2, B2 er CH2, O eller NH og fortrinsvis CH2.
12. Forbindelse ifølge krav 1, hvor: R2 er H, C(0)CH3, C(0)0t-Bu, C(0)0CH2Ph, C(0)0Et, C(O)O(CH2) 2OCH3, C(O)isobutyl, C(O)isopropyl, eller C(O)cyclo-Pr og fortrinsvis H, - Y er C-H, C-F, C-Cl, C-Br, C-CH3, C-CF3, C-cyclo-Pr, C-C^N, C-CH=CH2 eller N og fortrinsvis C-H, C-F eller N, - W er C-H eller N, - n er 0 eller 1 og fortrinsvis 0, - Z er N=CH eller NH-CH2, - R1 er Q3 med X er O, N-Me eller NH og fortrinsvis O, C1 er CH2 eller C (O), C2 er CH2, og C3 er O, CH2 eller NH.
13. Pesticid sammensætning, der omfatter en pesticid virkende mængde af mindst én forbindelse med formel (I) eller (!') ifølge krav 1.
14. Pesticid sammensætning ifølge krav 13, der foruden at omfatte forbindelsen med formel (I) eller (I') omfatter formuleringsadjuvanser.
15. Fremgangsmåde til bekæmpelse og kontrol af skadedyr med undtagelse af en fremgangsmåde til behandling af menneskeeller dyrekroppen ved hjælp af kirurgi eller terapi og diagnostiske metoder, der udøves på menneske- eller dyrekroppen, som omfatter påføring på et skadedyr, på et locus for et skadedyr eller på en plante, der er modtagelig for angreb af et skadedyr, af en pesticid virkende mængde af en forbindelse med formel (I) eller (I') ifølge krav 1.
16. Fremgangsmåde til bekæmpelse og kontrol af skadedyr med undtagelse af en fremgangsmåde til behandling af menneskeeller dyrekroppen ved hjælp af kirurgi eller terapi og diagnostiske metoder, der udøves på menneske- eller dyrekroppen, som omfatter påføring på et skadedyr, på et locus for et skadedyr eller på en plante, der er modtagelig for angreb af et skadedyr, af en pesticid sammensætning ifølge krav 13.
17. Fremgangsmåde til bekæmpelse og kontrol af insekter fra ordenen Hemiptera, som er resistente over for et neonicotinoid-insekticid, hvilken fremgangsmåde omfatter påføring af en forbindelse med formel (I) eller (I') ifølge krav 1 i fri form eller i en agrokemisk acceptabel saltform på de neonicotinoid-resistente insekter.
18. Planteformeringsmateriale, der omfatter en forbindelse med formel (I) eller (I') ifølge krav 1.
19. Forbindelse med formel (Villa):
hvor R1 er som defineret i krav 1, og Ra er Ci-Cgalkyl.
DK12787459.2T 2011-11-29 2012-11-20 Insekticide triazinonderivater DK2785708T3 (da)

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PCT/EP2012/073032 WO2013079350A1 (en) 2011-11-29 2012-11-20 Insecticidal triazinone derivatives

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EP (1) EP2785708B1 (da)
JP (1) JP6063953B2 (da)
CN (1) CN104011042B (da)
AU (1) AU2012344112B9 (da)
BR (1) BR112014012868B1 (da)
CA (1) CA2856453C (da)
DK (1) DK2785708T3 (da)
ES (1) ES2575212T3 (da)
HU (1) HUE029133T2 (da)
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AU2012344112A1 (en) 2014-06-19
US20140329819A1 (en) 2014-11-06
BR112014012868B1 (pt) 2019-12-17
AU2012344112B2 (en) 2016-12-08
CN104011042A (zh) 2014-08-27
PL2785708T3 (pl) 2017-11-30
CA2856453A1 (en) 2013-06-06
HUE029133T2 (en) 2017-02-28
BR112014012868A2 (pt) 2017-06-13
WO2013079350A1 (en) 2013-06-06
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US20150225387A1 (en) 2015-08-13
EP2785708B1 (en) 2016-03-23
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ES2575212T3 (es) 2016-06-27

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