AR123193A1 - BORON-CONTAINING COMPOUNDS AND THEIR USES - Google Patents

BORON-CONTAINING COMPOUNDS AND THEIR USES

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Publication number
AR123193A1
AR123193A1 ARP210102224A ARP210102224A AR123193A1 AR 123193 A1 AR123193 A1 AR 123193A1 AR P210102224 A ARP210102224 A AR P210102224A AR P210102224 A ARP210102224 A AR P210102224A AR 123193 A1 AR123193 A1 AR 123193A1
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Argentina
Prior art keywords
hydrocarbyl
substituted
partially
fully halogenated
cyclohydrocarbyl
Prior art date
Application number
ARP210102224A
Other languages
Spanish (es)
Inventor
Chunliang Liu
Chun Yu Liu
Yong Zhang
- Zhou Yasheen Kang
Christopher Michael Hahne
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5Metis Inc
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Publication of AR123193A1 publication Critical patent/AR123193A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

La presente invención contempla un compuesto que contiene boro, una composición que contiene una cantidad plaguicida eficaz de ese compuesto disuelto o disperso en un medio portador y un método para reducir, mejorar o controlar una infestación por una plaga, particularmente un hongo, mediante la administración de una composición contemplada a una planta o un animal que lo necesita. Reivindicación 1: Un compuesto de una, dos o la totalidad de las fórmulas estructurales (1), (2) y (3) o una forma de sal de él, caracterizado porque: Y es O ó S, donde, en la fórmula (2), cada Y es el mismo; X es halógeno, CN, S(hidrocarbilo de C₁₋₃), O(hidrocarbilo de C₁₋₃), arilo, arilo sustituido, heteroarilo o heteroarilo sustituido; n es un número seleccionado del grupo que consiste en: cero, 1, 2, 3 y 4, de manera tal que cuando n es cero, X esté ausente; R¹ se selecciona del grupo que consiste en: hidrógeno, hidrocarbilo de C₁₋₄ y ciclohidrocarbilo de C₃₋₄; y cuando n es 1 o más, R² es hidrocarbilo de C₁₋₆, hidrocarbilo de C₁₋₆ sustituido, ciclohidrocarbilo de C₃₋₆, ciclohidrocarbilo de C₃₋₆ sustituido, fenilo, fenilo sustituido, naftilo, naftilo sustituido, heteroarilo, heteroarilo sustituido, en donde el grupo hidrocarbilo de C₁₋₆ sustituido, ciclohidrocarbilo de C₃₋₆ sustituido, fenilo sustituido, naftilo sustituido o heteroarilo sustituido tiene 1, 2 ó 3 sustituyentes independientemente seleccionados de uno o más del grupo que consiste en: CN, hidrocarboiloxi (C₁₋₇), NO₂, OH, O(hidrocarbilo de C₁₋₆), O(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), S(hidrocarbilo de C₁₋₆), S(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), halógeno, hidrocarbilo de C₁₋₆, hidrocarbilo de C₁₋₆ parcial o totalmente halogenado, NHSO₂(hidrocarbilo de C₁₋₃), SO₂NH₂, SO₂(hidrocarbilo de C₁₋₃), NHC(O)(hidrocarbilo de C₁₋₃) y ciclohidrocarbilo de C₃₋₆; y cuando n es cero, R² es R²ᵃ, en donde: R²ᵃ es hidrocarbilo de C₁₋₆, hidrocarbilo de C₁₋₆ sustituido, ciclohidrocarbilo de C₃₋₆, ciclohidrocarbilo de C₃₋₆ sustituido, naftilo, naftilo sustituido, heteroarilo no sustituido diferente de piridilo o heteroarilo sustituido, en donde dicho grupo hidrocarbilo de C₁₋₆ sustituido, ciclohidrocarbilo de C₃₋₆ sustituido, naftilo sustituido o heteroarilo sustituido tiene 1, 2 ó 3 sustituyentes independientemente seleccionados de uno o más del grupo que consiste en: CN, hidrocarboiloxi (C₁₋₇), NO₂, OH, O(hidrocarbilo de C₁₋₆), O(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), S(hidrocarbilo de C₁₋₆), S(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), halógeno, hidrocarbilo de C₁₋₆, hidrocarbilo de C₁₋₆ parcial o totalmente halogenado, NHSO₂(hidrocarbilo de C₁₋₃), SO₂NH₂, SO₂(hidrocarbilo de C₁₋₃), NHC(O)(hidrocarbilo de C₁₋₃) y ciclohidrocarbilo de C₃₋₆; o R²ᵃ es fenilo sustituido que tiene 2 ó 3 sustituyentes seleccionados del grupo que consiste en: OH, O(hidrocarbilo de C₁₋₆), O(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), S(hidrocarbilo de C₁₋₆), S(hidrocarbilo de C₁₋₆ parcial y totalmente halogenado), halógeno, hidrocarbilo de C₁₋₆, hidrocarbilo de C₁₋₆ parcial y totalmente halogenado, NHSO₂(hidrocarbilo de C₁₋₃), SO₂NH₂, SO₂(hidrocarbilo de C₁₋₃) y NHC(O)(hidrocarbilo de C₁₋₃) o R²ᵃ es fenilo sustituido que tiene 1 sustituyente seleccionado del grupo que consiste en: OH, O(hidrocarbilo de C₁₋₆), O(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), S(hidrocarbilo de C₁₋₆), S(hidrocarbilo de C₁₋₆ parcial o totalmente halogenado), hidrocarbilo de C₁₋₆ parcial o totalmente halogenado, NHSO₂(hidrocarbilo de C₁₋₃), SO₂NH₂, SO₂(hidrocarbilo de C₁₋₃), NHC(O)(hidrocarbilo de C₁₋₃), halógeno que es meta con respecto al punto de unión al resto de la molécula, hidrocarbilo de C₁₋₆ que es orto o meta con respecto al punto de unión al resto de la molécula; en donde, en un compuesto de la fórmula (1), un X se puede combinar con el oxígeno ilustrado unido al átomo de boro y formar un anillo de entre 5 y 8 miembros, que puede contener uno o más heteroátomos adicionales seleccionados de N, O y S; en donde cada uno de dichos grupos fenilo o fenilo sustituido puede estar unido a través de un grupo hidrocarbilo de C₁₋₃ divalente; y en donde cada grupo heteroarilo contiene 1 anillo o 2 anillos fusionados que incluyen 1, 2 ó 3 heteroátomos del anillo que son iguales o diferentes y se seleccionan de uno o más de nitrógeno, oxígeno y azufre.The present invention contemplates a boron-containing compound, a composition containing a pesticidally effective amount of that compound dissolved or dispersed in a carrier medium, and a method of reducing, ameliorating, or controlling an infestation by a pest, particularly a fungus, by administering of a contemplated composition to a plant or an animal that needs it. Claim 1: A compound of one, two or all of the structural formulas (1), (2) and (3) or a salt form thereof, characterized in that: Y is O or S, where, in the formula ( 2), each Y is the same; X is halogen, CN, S(C₁₋₃ hydrocarbyl), O(C₁₋₃ hydrocarbyl), aryl, substituted aryl, heteroaryl, or substituted heteroaryl; n is a number selected from the group consisting of: zero, 1, 2, 3 and 4, such that when n is zero, X is absent; R¹ is selected from the group consisting of: hydrogen, C₁₋₄ hydrocarbyl and C₃₋₄ cyclohydrocarbyl; and when n is 1 or more, R² is C₁₋₆ hydrocarbyl, substituted C₁₋₆ hydrocarbyl, C₃₋₆ cyclohydrocarbyl, substituted C₃₋₆ cyclohydrocarbyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl, substituted heteroaryl , wherein the substituted C₁₋₆ hydrocarbyl, substituted C₃₋₆ cyclohydrocarbyl, substituted phenyl, substituted naphthyl, or substituted heteroaryl group has 1, 2, or 3 substituents independently selected from one or more from the group consisting of: CN, hydrocarboyloxy ( C₁₋₇), NO₂, OH, O(C₁₋₆ hydrocarbyl), O(C₁₋₆ hydrocarbyl partially or fully halogenated), S(C₁₋₆ hydrocarbyl), S(C₁₋₆ hydrocarbyl partially or fully halogenated), halogen, C₁₋₆ hydrocarbyl, partially or fully halogenated C₁₋₆ hydrocarbyl, NHSO₂(C₁₋₃ hydrocarbyl), SO₂NH₂, SO₂(C₁₋₃ hydrocarbyl), NHC(O)(C₁₋ hydrocarbyl ₃) and C₃₋₆ cyclohydrocarbyl; and when n is zero, R² is R²ᵃ, where: R²ᵃ is C₁₋₆ hydrocarbyl, substituted C₁₋₆ hydrocarbyl, C₃₋₆ cyclohydrocarbyl, substituted C₃₋₆ cyclohydrocarbyl, naphthyl, substituted naphthyl, different unsubstituted heteroaryl of substituted pyridyl or heteroaryl, wherein said substituted C₁₋₆ hydrocarbyl, substituted C₃₋₆ cyclohydrocarbyl, substituted naphthyl or substituted heteroaryl group has 1, 2 or 3 substituents independently selected from one or more of the group consisting of: CN, (C₁₋₆)hydrocarboyloxy, NO₂, OH, O(C₁₋₆ hydrocarbyl), O(partially or fully halogenated C₁₋₆ hydrocarbyl), S(C₁₋₆ hydrocarbyl), S(partial C₁₋₆ hydrocarbyl or fully halogenated), halogen, C₁₋₆ hydrocarbyl, partially or fully halogenated C₁₋₆ hydrocarbyl, NHSO₂(C₁₋₃ hydrocarbyl), SO₂NH₂, SO₂(C₁₋₃ hydrocarbyl), NHC(O)( C₁₋₃) and C₃₋₆ cyclohydrocarbyl; or R²ᵃ is substituted phenyl having 2 or 3 substituents selected from the group consisting of: OH, O(C₁₋₆ hydrocarbyl), O(partially or fully halogenated C₁₋₆ hydrocarbyl), S(C₁₋₆ hydrocarbyl) , S(partially and fully halogenated C₁₋₆ hydrocarbyl), halogen, C₁₋₆ hydrocarbyl, partially and fully halogenated C₁₋₆ hydrocarbyl, NHSO₂(C₁₋₃ hydrocarbyl), SO₂NH₂, SO₂(C₁₋₃ hydrocarbyl ) and NHC(O)(C₁₋₃ hydrocarbyl) or R²ᵃ is substituted phenyl having 1 substituent selected from the group consisting of: OH, O(C₁₋₆ hydrocarbyl), O(C₁₋₆ hydrocarbyl partially or wholly halogenated), S(C₁₋₆ hydrocarbyl), S(partially or fully halogenated C₁₋₆ hydrocarbyl), partially or fully halogenated C₁₋₆ hydrocarbyl, NHSO₂(C₁₋₃ hydrocarbyl), SO₂NH₂, SO₂( C₁₋₃), NHC(O)(C₁₋₃ hydrocarbyl), halogen which is meta with respect to the point of attachment to the rest of the molecule, C₁₋₆ hydrocarbyl which is ortho or meta with respect to the point of attachment n to the rest of the molecule; wherein, in a compound of formula (1), an X may combine with the illustrated oxygen attached to the boron atom to form a 5- to 8-membered ring, which may contain one or more additional heteroatoms selected from N, O and S; wherein each of said phenyl or substituted phenyl groups may be attached through a divalent C₁₋₃ hydrocarbyl group; and wherein each heteroaryl group contains 1 ring or 2 fused rings including 1, 2, or 3 ring heteroatoms that are the same or different and are selected from one or more of nitrogen, oxygen, and sulfur.

ARP210102224A 2020-08-10 2021-08-10 BORON-CONTAINING COMPOUNDS AND THEIR USES AR123193A1 (en)

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