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AR120868A1 - Tiofen-2-carboxamidas sustituidas y ácidos tiofen-2-carboxílicos sustituidos y sus derivados - Google Patents

Tiofen-2-carboxamidas sustituidas y ácidos tiofen-2-carboxílicos sustituidos y sus derivados

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Publication number
AR120868A1
AR120868A1 ARP200103606A ARP200103606A AR120868A1 AR 120868 A1 AR120868 A1 AR 120868A1 AR P200103606 A ARP200103606 A AR P200103606A AR P200103606 A ARP200103606 A AR P200103606A AR 120868 A1 AR120868 A1 AR 120868A1
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Argentina
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alkyl
halogen atoms
alkoxy
carbocycle
group
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ARP200103606A
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English (en)
Inventor
Jeremy Dufour
Lionel Nicolas
Thomas Knobloch
Stephane Brunet
Sybille Lamprecht
Tomoki Tsuchiya
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Bayer Ag
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Publication of AR120868A1 publication Critical patent/AR120868A1/es

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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
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    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
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    • 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
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
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    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Abstract

Compuestos derivados de tiofen-2-carboxamidas y de ácidos tiofen-2-carboxílicos; composición que comprende al menos uno de los derivados de tiofenocarboxamidas y el uso de ambos grupos de compuestos para controlar enfermedades bacterianas y/o fúngicas en plantas o partes de plantas. Reivindicación 1: Compuesto de la fórmula (1) en donde R¹ y R² se seleccionan, de modo independiente entre sí, del grupo que consiste en halógeno, ciano, alquilo C₁₋₆ o haloalquilo C₁₋₆, en donde al menos uno de R¹ o R² es halógeno; R³ se selecciona del grupo que consiste en hidrógeno, halógeno, ciano, alquilo C₁₋₆ o haloalquilo C₁₋₆; R⁴ y R⁵ se seleccionan, de modo independiente entre sí, del grupo que consiste en hidrógeno, halógeno, ciano, hidroxilo, alquilo C₁₋₆, hidroxialquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆, -O-C(=O)-alquilo C₁₋₆, carbociclo C₃₋₆, heterociclilo no aromático de 4, 5 ó 6 miembros, -C(=O)-NH₂, -C(=O)-NH(alquilo C₁₋₆), -C(=O)-N(alquilo C₁₋₆)₂, -C(=O)-OH, -C(=O)-O-alquilo C₁₋₆, arilo, heteroarilo de 5 a 9 miembros, -alquil C₁₋₆-alcoxi C₁₋₆, -alquil C₁₋₆-haloalquilo C₁₋₆, -alquil C₁₋₆-carbociclo C₃₋₆, -alquil C₁₋₆-heterociclilo no aromático de 4, 5 ó 6 miembros, -alquil C₁₋₆-arilo, -alquil C₁₋₆-hidroxiarilo, -alquil C₁₋₆-heteroarilo de 5 a 9 miembros, -alquil C₁₋₆-S-alquilo C₁₋₆, -alquil C₁₋₆-S-C(=O)-alquilo C₁₋₆, -alquil C₁₋₆-O-(C=O)-alquilo C₁₋₆, -alquil C₁₋₆-C(=O)-NH₂, -alquil C₁₋₆-C(=O)-NH(alquilo C₁₋₆), -alquil C₁₋₆-C(=O)-N(alquilo C₁₋₆)₂, -alquil C₁₋₆-C(=O)-OH, -alquil C₁₋₆-C(=O)-O-alquilo C₁₋₆, -alquil C₁₋₆-NH-C(=NH)-NH₂, -S-alquilo C₁₋₆, -S-C(=O)-alquilo C₁₋₆, -S-C(=O)-O-alquilo C₁₋₆, -S-C(=S)-O-alquilo C₁₋₆, -S-C(=O)-S-alquilo C₁₋₆, -S-C(=O)-NH₂, -S-C(=O)-NH(alquilo C₁₋₆), -S-C(=O)-NH(alquilo C₁₋₆)₂, -S-C(=S)-NH₂, -S-C(=S)-NH(alquilo C₁₋₆), -S-C(=S)-NH(alquilo C₁₋₆)₂, -alquil C₁₋₆-S-C(=O)-O-alquilo C₁₋₆, -alquil C₁₋₆-S-C(=O)-S-alquilo C₁₋₆, -alquil C₁₋₆-S-C(=O)-NH₂, -alquil C₁₋₆-S-C(=O)-NH(alquilo C₁₋₆), -alquil C₁₋₆-S-C(=O)-NH(alquilo C₁₋₆)₂, -alquil C₁₋₆-S-C(=S)-NH₂, -alquil C₁₋₆-S-C(=S)-NH(alquilo C₁₋₆), -alquil C₁₋₆-S-C(=S)-NH(alquilo C₁₋₆)₂, en donde los radicales cíclicos R⁴, R⁵ pueden estar sustituidos con uno o más sustituyentes de Rʷ, en donde los radicales cíclicos R⁴, R⁵ pueden estar sustituidos con uno o más sustituyentes de Rˣ, en donde al menos uno de R⁴ y R⁵ es hidrógeno, alquilo C₁₋₆ o carbociclo C₃₋₆ o R⁴ y R⁵ forman, junto con el átomo de carbono al que están unidos, un carbociclo C₃₋₆ o un heterociclo de 3 a 6 miembros, en donde dicho carbociclo C₃₋₆ y heterociclo de 3 a 6 miembros pueden estar sustituidos con uno o más sustituyentes de Rˣ, en donde Rʷ está seleccionado, de modo independiente, del grupo que consiste en nitro, hidroxilo, ciano, carboxilo, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoílo, carbamato, cicloalquilo C₃₋₇, halógenocicloalquilo C₃₋₇ que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-amino, di-alquil C₁₋₈-amino, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfanilo, halógenoalquil C₁₋₈-sulfanilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbonilo, halógenoalquil C₁₋₈-carbonilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbamoílo, di-alquil C₁₋₈-carbamoílo, alcoxi C₁₋₈-carbonilo, halógenoalcoxi C₁₋₈-carbonilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carboniloxi, halógenoalquil C₁₋₈-carboniloxi que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbonilamino, halógenoalquil C₁₋₈-carbonilamino que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfinilo, halógenoalquil C₁₋₈-sulfinilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfonilo, halógenoalquil C₁₋₈-sulfonilo que tiene 1 a 5 átomos de halógeno; alquil C₁₋₈-sulfonilamino, halógenoalquil C₁₋₈-sulfonilamino que tiene 1 a 5 átomos de halógeno; sulfamoílo; alquil C₁₋₈-sulfamoílo y di-alquil C₁₋₈-sulfamoílo, en donde Rˣ está seleccionado, de modo independiente, del grupo que consiste en halógeno, nitro, hidroxilo, ciano, carboxilo, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoílo, carbamato, alquilo C₁₋₈, cicloalquilo C₃₋₇, halógenoalquilo C₁₋₈ que tiene 1 a 5 átomos de halógeno, halógenocicloalquilo C₃₋₇ que tiene 1 a 5 átomos de halógeno, alquenilo C₂₋₈, alquinilo C₂₋₈, alquil C₁₋₈-amino, di-alquil C₁₋₈-amino, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfanilo, halógenoalquil C₁₋₈-sulfanilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbonilo, halógenoalquil C₁₋₈-carbonilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbamoílo, di-alquil C₁₋₈-carbamoílo, alcoxi C₁₋₈-carbonilo, halógenoalcoxi C₁₋₈-carbonilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carboniloxi, halógenoalquil C₁₋₈-carboniloxi que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-carbonilamino, halógenoalquil C₁₋₈-carbonilamino que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfanilo, halógenoalquil C₁₋₈-sulfanilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfinilo, halógenoalquil C₁₋₈-sulfinilo que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfonilo, halógenoalquil C₁₋₈-sulfonilo que tiene 1 a 5 átomos de halógeno; alquil C₁₋₈-sulfonilamino, halógenoalquil C₁₋₈-sulfonilamino que tiene 1 a 5 átomos de halógeno; sulfamoílo; alquil C₁₋₈-sulfamoílo y di-alquil C₁₋₈-sulfamoílo; R⁶ y R⁷ se seleccionan, de modo independiente, del grupo que consiste en hidrógeno, alquilo C₁₋₆, carbociclo C₃₋₆ o R⁶ y R⁷ forman, junto con el átomo de carbono al que están unidos, un carbociclo C₃₋₆ o un heterociclo de 3 a 6 miembros; n es 0 ó 1; W es oxígeno o azufre; Y es NR⁸, en donde R⁸ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, cianoalquilo C₁₋₆, hidroxi, alcoxi C₁₋₆ o carbociclo C₃₋₆; Z se selecciona del grupo que consiste en ciano, -C(=O)-ORᵃ, -C(=O)-SRᵃ, -C(=O)-NRᵇRᶜ, -C(=S)-NRᵇRᶜ o -C(=O)-NH-CRᵈRᵉ-C(=O)-ORᵃ, en donde Rᵃ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, cianoalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, arilo, aralquilo, heterociclilo no aromático de 4, 5 ó 6 miembros, -alquil C₁₋₆-Si(alquilo C₁₋₆)₃, -alquil C₁₋₆-cicloalquilo C₃₋₈, heteroarilo de 5 a 9 miembros y -alquil C₁₋₆-heteroarilo de 5 a 9 miembros o Rᵃ puede formar junto con R⁴ y con los átomos a los que están unidos, un heterociclo de 4 a 7 miembros, en donde Rᵇ y Rᶜ se seleccionan, de modo independiente, del grupo que consiste en hidrógeno, alquilo C₁₋₆, hidroxilo, alcoxi C₁₋₆, ciano, cianoalquilo C₁₋₆ o Rᵇ puede formar junto con R⁴ y con los átomos a los que están unidos, un heterociclo de 4 a 7 miembros, en donde Rᵈ y Rᵉ se seleccionan, de modo independiente, del grupo que consiste en hidrógeno, ciano, hidroxilo, alquilo C₁₋₆, hidroxialquilo C₁₋₆, alcoxi C₁₋₆, -O-C(=O)-alquilo C₁₋₆, carbociclo C₃₋₆, -C(=O)-NH₂, -C(=O)-NH(alquilo C₁₋₆), -C(=O)-N(alquilo C₁₋₆)₂, -C(=O)-OH, -C(=O)-O-alquilo C₁₋₆, arilo, heteroarilo de 5 a 9 miembros, -alquil C₁₋₆-alcoxi C₁₋₆, -alquil C₁₋₆-carbociclo C₃₋₆, -alquil C₁₋₆-arilo, -alquil C₁₋₆-hidroxiarilo, -alquil C₁₋₆-heteroarilo de 5 a 9 miembros, -alquil C₁₋₆-S-alquilo C₁₋₆, -alquil C₁₋₆-S-C(=O)-alquilo C₁₋₆, -alquil C₁₋₆-O-(C=O)-alquilo C₁₋₆, -alquil C₁₋₆-C(=O)-NH₂, -alquil C₁₋₆-C(=O)-NH(alquilo C₁₋₆), -alquil C₁₋₆-C(=O)-N(alquilo C₁₋₆)₂, -alquil C₁₋₆-C(=O)-OH, -alquil C₁₋₆-C(=O)-O-alquilo C₁₋₆, -alquil C₁₋₆-NH-C(=NH)-NH₂, en donde al menos uno de Rᵈ y Rᵉ es hidrógeno, alquilo C₁₋₆ o carbociclo C₃₋₆ o Rᵈ y Rᵉ forman, junto con el átomo de carbono al que están unidos, un carbonilo, carbociclo C₃₋₆ o un heterociclo de 3 a 6 miembros; siempre que se excluyan los compuestos de la fórmula (1) con las siguientes combinaciones de R¹, R² y R³ @@@@@@@@@
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