AR092293A1 - Amidas de acido n-(1,2,5-oxadiazol-3-il)-, n-(1,3,4-oxadiazol-2-il)-, n-(tetrazol-5-il)- y n-(triazol-5-il)-arilcarboxilico y su uso como herbicidas - Google Patents

Amidas de acido n-(1,2,5-oxadiazol-3-il)-, n-(1,3,4-oxadiazol-2-il)-, n-(tetrazol-5-il)- y n-(triazol-5-il)-arilcarboxilico y su uso como herbicidas

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AR092293A1
AR092293A1 ARP120104604A ARP120104604A AR092293A1 AR 092293 A1 AR092293 A1 AR 092293A1 AR P120104604 A ARP120104604 A AR P120104604A AR P120104604 A ARP120104604 A AR P120104604A AR 092293 A1 AR092293 A1 AR 092293A1
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Argentina
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alkyl
halogen
cycloalkyl
heterocyclyl
alkynyl
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ARP120104604A
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Dr Lehr Stefan
Hugh Dr Rosinger Christopher
Dr Gatzweiler Elmar
Dr Drner-Rieping Simon
Dr Khn Arnim
Dr Braun Ralf
Dr Ahrens Hartmut
Dr Huser-Hahn Isolde
Dr Dietrich Hansjrg
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Bayer Ip Gmbh
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Publication of AR092293A1 publication Critical patent/AR092293A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—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
    • A01N43/64—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
    • 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
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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
    • A01N43/72—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
    • A01N43/82—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 three ring hetero 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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    • C07—ORGANIC CHEMISTRY
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
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    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • 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
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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
    • C07D403/12—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
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    • C07—ORGANIC CHEMISTRY
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    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
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    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Se describen amidas de ácido N-(1,2,5-oxadiazol-3-il)-, N-(1,3,4-oxadiazol-2-il)-, N-(tetrazol-5-il)- y N-(triazol-5-il)-arilcarboxílico de la fórmula general (1) como herbicidas. Reivindicación 1: Amidas de ácido N-(1,2,5-oxadiazol-3-il)-, N-(1,3,4-oxadiazol-2-il)-, N(tetrazol-5-il)- y N-(triazol-5-il)-arilcarboxílico de la fórmula (1) o sus sales, en la que R significa alquilo C₁₋₆, halógenoalquilo C₁₋₆, alquenilo C₂₋₆, halógenoalquenilo C₂₋₆, alquinilo C₂₋₆, halógenoalquinilo C₃₋₆, cicloalquilo C₃₋₆, halógenocicloalquilo C₃₋₆, cicloalquil C₃₋₆- alquilo C₁₋₆, halógeno-cicloalquil C₃₋₆-alquilo C₁₋₆, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-COOR¹, alquil C₁₋₆-C(O)R¹, alquil C₁₋₆-CN, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², OR¹, COOR¹, CON(R¹)₂, N(R¹)₂, NR¹COOR¹, NR¹CON(R¹)₂ o bencilo sustituido respectivamente con s restos del grupo metilo, etilo, metoxi, nitro, trifluorometilo y halógeno; W significa N o CY; X y Z significan independientemente entre sí respectivamente hidrógeno, nitro, halógeno, ciano, formilo, sulfociano, alquilo C₁₋₆, halógenoalquilo C₁₋₆, alquenilo C₂₋₆, halógenoalquenilo C₂₋₆, alquinilo C₂₋₆, halógenoalquinilo C₃₋₆, cicloalquilo C₃₋₆, halógenocicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, halógeno-cicloalquil C₃₋₆-alquilo C₁₋₆, COR¹, OR¹, OCOR¹, OSO₂R², S(O)ₙR², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-COOR¹, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂, o heteroarilo, heterociclilo o fenilo sustituido respectivamente con s restos del grupo metilo, etilo, metoxi, nitro, trifluorometilo y halógeno; Y significa hidrógeno, nitro, halógeno, ciano, sulfociano, alquilo C₁₋₆, halógeno-alquilo C₁₋₆, alquenilo C₂₋₆, halógeno-alquenilo C₂₋₆, alquinilo C₂₋₆, halógeno-alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógeno-cicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, halógeno-cicloalquil C₃₋₆-alquilo C₁₋₆, COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)N(R¹)OR¹, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)ₙR², SO₂OR¹, SO₂N(R¹)₂, alquil C₁₋₆-S(O)ₙR², alquil C₁₋₆-OR¹, alquil C₁₋₆-OCOR¹, alquil C₁₋₆-OSO₂R², alquil C₁₋₆-CO₂R¹, alquil C₁₋₆-CN, alquil C₁₋₆-SO₂OR¹, alquil C₁₋₆-CON(R¹)₂, alquil C₁₋₆-SO₂N(R¹)₂, alquil C₁₋₆-NR¹COR¹, alquil C₁₋₆-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, CH=NOR¹, alquil C₁₋₆-CHNOR¹, alquil C₁₋₆-O-NC(R¹)₂, alquil C₁₋₆-fenilo, alquil C₁₋₆-heteroarilo, alquil C₁₋₆-heterociclilo, fenilo, heteroarilo o heterociclilo, donde los 6 restos mencionados por último están sustituidos respectivamente con s restos del grupo que se compone de halógeno, nitro, ciano, alquilo C₁₋₆, halógeno-alquilo C₁₋₆, cicloalquilo C₃₋₆, S(O)-alquilo C₁₋₆, alcoxi C₁₋₆, halógeno-alcoxi C₁₋₆, alcoxi alquilo C₁₋₆ C₁₋₄ y cianometilo, y donde heterociclilo porta n grupos oxo, o Y y Z forman, junto con los dos átomos a los que están unidos, un anillo de 5, 6 ó 7 miembros, insaturado, parcialmente saturado o saturado, que además de átomos de carbono respectivamente comprende s átomos de nitrógeno, n átomos de oxígeno, n átomos de azufre y n elementos S(O), S(O)₂, C=N-R¹⁷, C(OR¹⁷)₂, C[-O-(CH₂)₂-O-] o C(O) como miembros del anillo, cuyos átomos de carbono están sustituidos con s restos del grupo que se compone de halógeno, ciano, alquilo C₁₋₆, alquenilo C₂₋₁₀, alquinilo C₂₋₁₀, haloalquilo C₁₋₆, alcoxi C₁₋₆, fenoxi, halógeno-alcoxi C₁₋₆, cicloalquilo C₃₋₈, alcoxialquilo C₂₋₈ y fenilo, cuyos átomos de nitrógeno están sustituidos con n restos del grupo que se compone de alquilo C₁₋₆ y fenilo, y donde los restos fenilo antes mencionados están sustituidos con s restos del grupo que se compone de ciano, nitro, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆ y alcoxi C₁₋₆; V significa hidrógeno, nitro, halógeno, ciano, alquilo C₁₋₄, halógenoalquilo C₁₋₄, OR¹, S(O)ₙR²; R¹ significa hidrógeno, alquilo C₁₋₆, halógenoalquilo C₁₋₆, alquenilo C₂₋₆, halógenoalquenilo C₂₋₆, alquinilo C₂₋₆, halógenoalquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógenocicloalquilo C₃₋₆, alquil C₁₋₆-O-alquilo C₁₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, fenilo, fenil-alquilo C₁₋₆, heteroarilo, alquil C₁₋₆-heteroarilo, heterociclo, alquil C₁₋₆-heterociclilo, alquil C₁₋₆-O-heteroarilo, alquil C₁₋₆-O-heterociclilo, alquil C₁₋₆-NR³-heteroarilo, alquil C₁₋₆-NR³-heterociclilo, donde los 21 restos mencionados por último están sustituidos con s restos del grupo que se compone de ciano, halógeno, nitro, sulfociano, OR³, S(O)ₙR⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ y alcoxi C₁₋₄-alcoxicarbonilo C₂₋₆, y donde heterociclilo porta n grupos oxo; R² significa alquilo C₁₋₆, halógenoalquilo C₁₋₆, alquenilo C₂₋₆, halógenoalquenilo C₂₋₆, alquinilo C₂₋₆, halógenoalquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₃₋₆, halógenocicloalquilo C₃₋₆, alquil C₁₋₆-O-alquilo C₁₋₆, cicloalquil C₃₋₆-alquilo C₁₋₆, fenilo, fenil-alquilo C₁₋₆, heteroarilo, alquil C₁₋₆-heteroarilo, heterociclilo, alquil C₁₋₆-heterociclilo, alquil C₁₋₆-O-heteroarilo, alquil C₁₋₆-O-heterociclilo, alquil C₁₋₆-NR³-heteroarilo, alquil C₁₋₆-NR³-heterociclilo, donde los 21 restos mencionados por último están sustituidos con s restos del grupo que se compone de ciano, halógeno, nitro, sulfociano, OR³, S(O)ₙR⁴, N(R³)₂, NR³OR³, COR³, OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ y alcoxi C₁₋₄-alcoxicarbonilo C₂₋₆, y donde heterociclilo porta n grupos oxo; R³ significa hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆ o cicloalquil C₃₋₆-alquilo C₁₋₆; R⁴ significa alquilo C₁₋₆, alquenilo C₂₋₆ o alquinilo C₂₋₆, cicloalquilo C₃₋₆ o cicloalquil C₃₋₆-alquilo C₁₋₆; R⁵ significa alquilo C₁₋₄; n significa 0, 1 ó 2; s significa 0, 1, 2 ó 3; Q significa un resto de fórmula (Q1), (Q2), (Q3) ó (Q4); R⁶ significa alquilo C₁₋₆, halógeno-alquilo C₁₋₆, alquenilo C₂₋₆, halógeno-alquenilo C₂₋₆, alquinilo C₂₋₆, halógeno-alquinilo C
ARP120104604A 2011-12-13 2012-12-07 Amidas de acido n-(1,2,5-oxadiazol-3-il)-, n-(1,3,4-oxadiazol-2-il)-, n-(tetrazol-5-il)- y n-(triazol-5-il)-arilcarboxilico y su uso como herbicidas AR092293A1 (es)

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WO2013087577A1 (de) 2013-06-20
ZA201403565B (en) 2015-07-29
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AU2012350749A1 (en) 2014-07-10
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BR112014013872B1 (pt) 2019-11-19
MX352628B (es) 2017-12-01
US9204650B2 (en) 2015-12-08
HK1200832A1 (en) 2015-08-14
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BR112014013872A2 (pt) 2017-06-13
CA2858757C (en) 2019-02-12
ES2622579T3 (es) 2017-07-06
AU2012350749B2 (en) 2017-02-23
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