AR119203A1 - HYDROXYISOXAZOLINES AND DERIVATIVES THEREOF - Google Patents

HYDROXYISOXAZOLINES AND DERIVATIVES THEREOF

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Publication number
AR119203A1
AR119203A1 ARP200101741A ARP200101741A AR119203A1 AR 119203 A1 AR119203 A1 AR 119203A1 AR P200101741 A ARP200101741 A AR P200101741A AR P200101741 A ARP200101741 A AR P200101741A AR 119203 A1 AR119203 A1 AR 119203A1
Authority
AR
Argentina
Prior art keywords
alkyl
halo
trifluoromethyl
oxazol
dihydro
Prior art date
Application number
ARP200101741A
Other languages
Spanish (es)
Inventor
Anne Rebstock
- Desbordes Philippe Sophie
Jeremy Dufour
Pierre Coqueron
- Naud Sebastien Yves
Pierre Genix
Vincent Thomas
Sophie Ducerf
Aurelie Mallinger
Jacopo Negroni
Grtz Andreas Dr
Braun Christoph Andreas Dr
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of AR119203A1 publication Critical patent/AR119203A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • 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
    • C07D413/02—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
    • C07D413/04—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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Reivindicación 1: Un compuesto que posee la fórmula (1) siendo que R¹ se selecciona a partir del conjunto que consiste en hidrógeno, C₁₋₈-alquilo, C₃₋₈-cicloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, -C₁₋₈-alquil-arilo, -C₁₋₈-alquil-C₁₋₈-alcoxi, -Si(C₁₋₈-alquil)₃, -Si-aril(C₁₋₈-alquil)₂, -C₁₋₈-alquil-C₃₋₈-cicloalquilo, arilo, heteroarilo, -C₁₋₈-alquil-heteroarilo, di-C₁₋₈-alquil-fosfato, -C(=O)Rᵃ, -C(=S)Rᵃ, -C(=O)N(Rᵃ)₂, -C₁₋₆-alquil-OC(=O)Rᵃ y -C₁₋₆-alquil-C(=O)Rᵃ, siendo que Rᵃ se selecciona a partir del conjunto que consiste en hidrógeno, amino, C₁₋₁₀-alquilo, C₁₋₆-haloalquilo, C₂₋₈-alquenilo, C₂₋₈-haloalquenilo, C₂₋₈-alquinilo, C₂₋₈-haloalquinilo, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi, C₁₋₈-alquilsulfanilo, C₁₋₈-alquilamino, di-C₁₋₈-alquilamino, -C₁₋₆-alquil-C₁₋₆-alcoxi, C₃₋₁₀-carbociclilo, C₃₋₁₀-halocarbociclilo, heterociclilo de 3 a 10 miembros, arilo, heteroarilo, heterocicliloxi, ariloxi y heteroariloxi, siendo que los radicales R¹ o Rᵃ acíclicos pueden estar sustituidos con uno o más sustituyentes R¹ᵃ y siendo que los radicales R¹ o Rᵃ cíclicos pueden estar sustituidos con uno o más sustituyentes R¹ᶜ; A representa un compuesto del grupo de fórmulas (2), siendo que A-1, A-2, A-3 y A-4 opcionalmente están sustituidos con uno o dos flúor; Y se selecciona en forma independiente a partir del conjunto que consiste en cloro, bromo, yodo, CN, formilo, COCH₃, CO₂H, CONH₂, C(=NOH)H, C(=NOH)CH₃, C(=NOCH₃)H, C(=NOCH₃)CH₃, CH₂Cl, CH₂Br, CH₂I, CH₂OH, CH₂OCH₃, CH₂OC(=O)CH₃, CH₂NH₂, CH₂SH, CH₂SCH₃, CH₂SCF₃, OH, OCF₃, OCHF₂, OCH₃, OC(=O)CH₃, OS(O)₂CH₃, SH, SCF₃, SCH₃, S(O)CH₃, S(O)₂CH₃, SF₅, CH₃, CF₃, CHF₂, NH₂, CF₂Br, CF₂I, CF₂Cl, CCH, isociano y NO₂; siendo que A-1 está sustituido con uno o dos átomos de flúor cuando R¹ es hidrógeno y es cloro, bromo, COMe, CO₂H, CONH₂, C(=NOH)CH₃, C(=NOCH₃)CH₃, CH₂Cl, CH₂OH, CH₂NH₂, OH, OCH₃, OCF₃, SMe, S(O)₂Me, SCF₃, SF₅, CH₃ o NH₂; siendo que A-4 está sustituido con uno o dos átomos de flúor cuando R¹ es hidrógeno y es cloro, bromo o CH₃; y siendo que R¹ᵃ y R¹ᶜ considerados en forma independiente se seleccionan a partir del conjunto que consiste en átomo de halógeno, nitro, hidroxilo, ciano, carboxilo, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoilo, carbamato, C₁₋₆-alquilo, C₃₋₇-cicloalquilo, C₁₋₆-haloalquilo, C₃₋₈-halocicloalquilo, C₂₋₆-(halo)alquenilo, C₂₋₆-(halo)alquinilo, C₁₋₆-alquilamino, di-C₁₋₆-alquilamino, -Si(C₁₋₆-alquil)₃, C₁₋₆-(halo)alcoxiC₁₋₆-(halo)alquilsulfanilo, C₁₋₆-(halo)alquilcarbonilo, C₁₋₆-alquilcarbamoilo, di-C₁₋₆-alquilcarbamoilo, C₁₋₆-(halo)alcoxicarbonilo, ariloxi, C₁₋₆-(halo)alquilcarboniloxi, C₁₋₆-(halo)alquilcarbonilamino, C₁₋₈-(halo)alquilsulfanilo, C₁₋₈-(halo)alquilsulfinilo, C₁₋₈-(halo)alquilsulfonilo, C₁₋₈-alquilsulfonilamino, C₁₋₈-haloalquilsulfonilamino, sulfamoilo, C₁₋₈-alquilsulfamoilo y di-C₁₋₈-alquilsulfamoilo; o una sal, N-óxido o solvato de [la estructura representada por dicha fórmula]; siendo que el compuesto que posee la fórmula (1) no es: ácido 3-fluoro-4-[5-hidroxi-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-3-il)benzoico; ter-butil carbonato de 3-(4-bromofenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ilo; 3-(4-aminofenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ilo pirrolidina-1-carboxilato; 3-(3-fluoro-4-hidroxifenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ol; 3-[3-fluoro-4-(trifluorometil)fenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ol; 3-(4-clorofenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ilo acetato; ni 3-(4-bromofenil)-5-(trifluorometil)-4,5-dihidro-1,2-oxazol-5-ilo acetato.Claim 1: A compound having formula (1) wherein R¹ is selected from the group consisting of hydrogen, C₁₋₈-alkyl, C₃₋₈-cycloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, -C₁₋₈-alkyl-aryl, -C₁₋₈-alkyl-C₁₋₈-alkoxy, -Si(C₁₋₈-alkyl)₃, -Si-aryl(C₁₋₈-alkyl)₂, -C₁₋₈ -C₃₋₈-alkyl-cycloalkyl, aryl, heteroaryl, -C₁₋₈-alkyl-heteroaryl, di-C₁₋₈-alkyl-phosphate, -C(=O)Rᵃ, -C(=S)Rᵃ, -C (=O)N(Rᵃ)₂, -C₁₋₆-alkyl-OC(=O)Rᵃ and -C₁₋₆-alkyl-C(=O)Rᵃ, where Rᵃ is selected from the set consisting of hydrogen, amino, C₁₋₁₀-alkyl, C₁₋₆-haloalkyl, C₂₋₈-alkenyl, C₂₋₈-haloalkenyl, C₂₋₈-alkynyl, C₂₋₈-haloalkynyl, C₁₋₈-alkoxy, C₁₋₈- haloalkoxy, C₁₋₈-alkylsulfanyl, C₁₋₈-alkylamino, di-C₁₋₈-alkylamino, -C₁₋₆-alkyl-C₁₋₆-alkoxy, C₃₋₁₀-carbocyclyl, C₃₋₁₀-halocarbocyclyl, 3-heterocyclyl to 10 members, aryl, heteroaryl, heterocyclyloxy, aryloxy and heteroaryloxy, where the acyclic radicals R¹ or Rᵃ may be substituted with one or more of their R¹ᵃ substituents and where the cyclic R¹ or Rᵃ radicals may be substituted with one or more R¹ᶜ substituents; A represents a compound of the group of formulas (2), where A-1, A-2, A-3 and A-4 are optionally substituted with one or two fluorines; Y is independently selected from the set consisting of chlorine, bromine, iodine, CN, formyl, COCH₃, CO₂H, CONH₂, C(=NOH)H, C(=NOH)CH₃, C(=NOCH₃)H, C(=NOCH₃)CH₃, CH₂Cl, CH₂Br, CH₂I, CH₂OH, CH₂OCH₃, CH₂OC(=O)CH₃, CH₂NH₂, CH₂SH, CH₂SCH₃, CH₂SCF₃, OH, OCF₃, OCHF₂, OCH₃, OC(O, OS)CH )₂CH₃, SH, SCF₃, SCH₃, S(O)CH₃, S(O)₂CH₃, SF₅, CH₃, CF₃, CHF₂, NH₂, CF₂Br, CF₂I, CF₂Cl, CCH, isocyan and NO₂; where A-1 is substituted with one or two fluorine atoms when R¹ is hydrogen and is chlorine, bromine, COMe, CO₂H, CONH₂, C(=NOH)CH₃, C(=NOCH₃)CH₃, CH₂Cl, CH₂OH, CH₂NH₂, OH, OCH₃, OCF₃, SMe, S(O)₂Me, SCF₃, SF₅, CH₃, or NH₂; where A-4 is substituted with one or two fluorine atoms when R¹ is hydrogen and is chlorine, bromine or CH₃; and where R¹ᵃ and R¹ᶜ taken independently are selected from the group consisting of halogen atom, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-l⁶-sulfanyl, formyl, carbamoyl, carbamate, C₁₋₆ -alkyl, C₃₋₇-cycloalkyl, C₁₋₆-haloalkyl, C₃₋₈-halocycloalkyl, C₂₋₆-(halo)alkenyl, C₂₋₆-(halo)alkynyl, C₁₋₆-alkylamino, di-C₁₋₆ -alkylamino, -Si(C₁₋₆-alkyl)₃, C₁₋₆-(halo)C₁₋₆alkoxy-(halo)alkylsulfanyl, C₁₋₆-(halo)alkylcarbonyl, C₁₋₆-alkylcarbamoyl, di-C₁₋₆ -alkylcarbamoyl, C₁₋₆-(halo)alkoxycarbonyl, aryloxy, C₁₋₆-(halo)alkylcarbonyloxy, C₁₋₆-(halo)alkylcarbonylamino, C₁₋₈-(halo)alkylsulfanyl, C₁₋₈-(halo)alkylsulfinyl, C₁₋₈-(halo)alkylsulfonyl, C₁₋₈-alkylsulfonylamino, C₁₋₈-haloalkylsulfonylamino, sulfamoyl, C₁₋₈-alkylsulfamoyl, and di-C₁₋₈-alkylsulfamoyl; or a salt, N-oxide or solvate of [the structure represented by said formula]; wherein the compound having the formula (1) is not: 3-fluoro-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl)benzoic acid; 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-yl tert-butyl carbonate; 3-(4-aminophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-yl pyrrolidine-1-carboxylate; 3-(3-fluoro-4-hydroxyphenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol; 3-[3-fluoro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol; 3-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-yl acetate; nor 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-yl acetate.

ARP200101741A 2019-06-21 2020-06-19 HYDROXYISOXAZOLINES AND DERIVATIVES THEREOF AR119203A1 (en)

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EP (1) EP3986876A1 (en)
AR (1) AR119203A1 (en)
BR (1) BR112021025865A2 (en)
TW (1) TW202115000A (en)
UY (1) UY38764A (en)
WO (1) WO2020254492A1 (en)

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TW202115000A (en) 2021-04-16
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BR112021025865A2 (en) 2022-03-03
UY38764A (en) 2021-01-29

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