AR119218A1 - OXADIAZOLE FUNGICIDES - Google Patents

OXADIAZOLE FUNGICIDES

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Publication number
AR119218A1
AR119218A1 ARP200101757A ARP200101757A AR119218A1 AR 119218 A1 AR119218 A1 AR 119218A1 AR P200101757 A ARP200101757 A AR P200101757A AR P200101757 A ARP200101757 A AR P200101757A AR 119218 A1 AR119218 A1 AR 119218A1
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Argentina
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alkyl
haloalkyl
aryl
heteroaryl
carbocyclyl
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ARP200101757A
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Spanish (es)
Inventor
Anne Rebstock
- Desbordes Philippe Sophie
Jeremy Dufour
Pierre Coqueron
- Genix Pierre Yves
Vincent Thomas
Sophie Ducerf
Grtz Andreas Dr
Braun Christoph Andreas Dr
Aurelie Mallinger
Jacopo Negroni
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Bayer Ag
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Publication of AR119218A1 publication Critical patent/AR119218A1/en

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    • 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
    • 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
    • A01N43/82—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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

Abstract

Reivindicación 1: Uso de un compuesto conforme a la fórmula (1) para controlar hongos fitopatogénicos en plantas, siendo que X es flúor o cloro; R¹, R² considerados en forma independiente se seleccionan a partir del conjunto que consiste en hidrógeno, ciano, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₂₋₈-alquenilo, C₂₋₈-haloalquenilo, C₂₋₈-alquinilo, C₂₋₈-haloalquinilo, C₃₋₇-carbociclilo, arilo, heterociclilo de 3 a 10 miembros, heteroarilo, aril-C₁₋₈-alquilo, heterociclilo de 3 a 10 miembros-C₁₋₈-alquilo, heteroaril-C₁₋₈-alquilo y C₃₋₇-carbociclil-C₁₋₈-alquilo, siendo que dichos R¹ y R² acíclicos pueden estar sustituidos con, respectivamente, uno o más sustituyentes R¹ᵃ y R²ᵃ y dichos R¹ y R² cíclicos pueden estar sustituidos con, respectivamente, uno o más sustituyentes R¹ᵇ y R²ᵇ, o R¹, R² pueden formar, junto con el átomo de carbono al que están unidos, un C₃₋₇-carbociclilo o un heterociclilo de 3 a 10 miembros, siendo que dicho C₃₋₇-carbociclilo o heterociclilo de 3 a 10 miembros puede estar sustituido con uno o más sustituyentes R¹ᵇ; Cy es arilo, heteroarilo, C₃₋₁₀-carbociclilo o heterociclilo de 3 a 10 miembros; n es 0, 1, 2, 3 ó 4; R³ considerado en forma independiente se selecciona a partir del conjunto que consiste en halógeno, ciano, hidroxi, amino, nitro, carboxilo, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoilo, carbamato, C₁₋₆-alquilo, C₁₋₆-cianoalquilo, C₁₋₆-haloalquilo, C₂₋₆-alquenilo, C₂₋₆-haloalquenilo, C₂₋₆-alquinilo, C₂₋₆-haloalquinilo, C₁₋₆-alcoxi, C₁₋₆-haloalcoxi, C₁₋₆-alcoxi-C₁₋₆-alquilo, C₁₋₆-alquilsulfanilo, C₁₋₆-haloalquilsulfanilo, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₃₋₇-carbociclilo, C₃₋₇-halocarbociclilo, C₁₋₆-hidroxialquilo, C₁₋₆-alquilamino, di-C₁₋₆-alquilamino, C₁₋₆-alquilcarbonilo, C₁₋₆-alcoxicarbonilo, C₁₋₆-haloalcoxicarbonilo, C₁₋₆-alquilcarbamoilo, di-C₁₋₆-alquilcarbamoilo, aminocarbonilo, C₁₋₈-alquilcarboniloxi, C₁₋₈-haloalquilcarboniloxi, C₁₋₈-alquilcarbonilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₆-alquilsulfonilamino, C₁₋₆-haloalquilsulfonilamino, sulfamoilo, C₁₋₈-alquilsulfamoilo, di-C₁₋₈-alquilsulfamoilo, arilo (por ejemplo fenilo), aril-C₁₋₆-alquilo y heteroarilo, siendo que dichos R³ acíclicos y cíclicos pueden estar sustituidos con uno o más sustituyentes, los cuales pueden ser el mismo o diferentes, a seleccionar a partir del conjunto que consiste en halógeno, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi y C₁₋₆-haloalcoxi; R⁴ se selecciona a partir del conjunto que consiste en hidrógeno, hidroxi, formilo, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₂₋₆-alquenilo, C₂₋₆-haloalquenilo, C₂₋₆-alquinilo, C₂₋₆-haloalquinilo, -C(=O)-C₁₋₆-alquilo, -C(=O)-C₁₋₆-haloalquilo, -C(=S)-C₁₋₆-alquilo, -C(=S)-C₁₋₆-haloalquilo, -C(=O)-O-C₁₋₆-alquilo, -C(=O)-O-C₁₋₆-haloalquilo, C₁₋₆-alcoxi, C₁₋₆-haloalcoxi, C₁₋₆-alquilsulfonilo, C₁₋₆-haloalquilsulfonilo, fenilsulfonilo, C₃₋₁₀-carbociclilo, heterociclilo de 3 a 10 miembros, arilo (fenilo), heteroarilo, C₃₋₁₀-carbociclil-C₁₋₆-alquilo, C₃₋₁₀-carbociclil-C₁₋₆-haloalquilo, aril-C₁₋₆-alquilo, aril-C₁₋₆-haloalquilo, heteroaril-C₁₋₆-alquilo y heteroaril-C₁₋₆-haloalquilo, siendo que dichos R⁴ cíclicos y acíclicos pueden estar sustituidos con uno o más sustituyentes a seleccionar a partir del conjunto que consiste en halógeno, ciano, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi y C₁₋₆-haloalcoxi; R⁵ es hidrógeno o flúor; R¹ᵃ, R²ᵃ considerados en forma independiente se seleccionan a partir del conjunto que consiste en nitro, hidroxilo, ciano, carboxilo, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoilo, carbamato, C₃₋₇-cicloalquilo, C₃₋₇-halocicloalquilo, C₁₋₈-alquilamino, di-C₁₋₈-alquilamino, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi, C₁₋₈-alquilsulfanilo, C₁₋₈-haloalquilsulfanilo, C₁₋₈-alquilcarbonilo, C₁₋₈-haloalquilcarbonilo, C₁₋₈-alquilcarbamoilo, di-C₁₋₈-alquilcarbamoilo, C₁₋₈-alcoxicarbonilo, C₁₋₈-haloalcoxicarbonilo, C₁₋₈-alquilcarboniloxi, C₁₋₈-haloalquilcarboniloxi, C₁₋₈-alquilcarbonilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₁₋₈-alquilsulfonilamino, C₁₋₈-haloalquilsulfonilamino, sulfamoilo, C₁₋₈-alquilsulfamoilo y di-C₁₋₈-alquilsulfamoilo; R¹ᵇ, R²ᵇ considerados en forma independiente se seleccionan a partir del conjunto que consiste en halógeno, ciano, hidroxi, amino, nitro, carboxilo, sulfanilo, pentafluoro-l⁶-sulfanilo, formilo, carbamoilo, carbamato, C₁₋₆-alquilo, C₁₋₆-cianoalquilo, C₁₋₆-haloalquilo, C₂₋₆-alquenilo, C₂₋₆-haloalquenilo, C₂₋₆-alquinilo, C₂₋₆-haloalquinilo, C₁₋₆-alcoxi, C₁₋₆-haloalcoxi, C₁₋₆-alcoxiC₁₋₆-alquilo, C₁₋₆-alquilsulfanilo, C₁₋₆-haloalquilsulfanilo, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₁₋₆-alquil-C(=O)-NH-, C₃₋₇-carbociclilo, C₃₋₇-halocarbociclilo, hidroxi-C₁₋₆-alquilo, C₁₋₆-alquilamino, di-C₁₋₆-alquilamino, C₁₋₆-alquilcarbonilo, C₁₋₆-alcoxicarbonilo, C₁₋₆-haloalcoxicarbonilo, C₁₋₆-alquilcarbamoilo, di-C₁₋₆-alquilcarbamoilo, aminocarbonilo, C₁₋₈-alquilcarboniloxi, C₁₋₈-haloalquilcarboniloxi, C₁₋₈-alquilcarbonilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₆-alquilsulfonilamino, C₁₋₆-haloalquilsulfonilamino, sulfamoilo, C₁₋₈-alquilsulfamoilo, di-C₁₋₈-alquilsulfamoilo, arilo (por ejemplo fenilo), aril-C₁₋₆-alquilo y heteroarilo, siendo que dicho arilo (fenilo) o heteroarilo opcionalmente está sustituido con uno o más sustituyentes, los cuales pueden ser el mismo o diferentes, a seleccionar a partir del conjunto que consiste en halógeno, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi y C₁₋₆-haloalcoxi; o una sal N-óxido o solvato de dicha estructura; siendo que el compuesto conforme a la fórmula (1) no es: (a) N-[1-(piridin-2-il)ciclobutil)-5-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]pirimidin-2-amina; (b) 5-{5-[cloro(difluoro)metil)-1,2,4-oxadiazol-3-il}-N-[1-(piridin-2-il)ciclobutil]pirimidin-2-amina; (c) N-(1-fenilciclopropil)-5-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]pirimidin-2-amina; (d) 5-{5-[cloro(difluoro)metil)-1,2,4-oxadiazol-3-il}-N-(1-fenilciclopropil)pirimidin-2-amina. Reivindicación 13: Un método para controlar hongos fitopatogénicos que comprende el paso de aplicar al menos un compuesto conforme a la fórmula (1) conforme a una cualquiera de las reivindicaciones 1 a 12 a las plantas, las partes de planta, las semillas, las frutas o el suelo en el que crecen las plantas. Reivindicación 14: Un compuesto conforme a la fórmula (1’) o un sal, N-óxido o solvato de dicha estructura; siendo que X, R¹, R², R³, R⁴, R⁵, Cy y n son tal como se definen en cualquiera de las reivindicaciones 1 a 12, siendo que cuando X es flúor y R⁴ es hidrógeno o C₁₋₆-alquilo, R¹ y R² no son ambos hidrógeno; siendo que se excluyen los compuestos en los que X es flúor, Cy es fenilo o heteroarilo de 6 miembros, n es 0 y R¹, R² y R⁴ se seleccionan, considerando cada uno en forma independiente, a partir de hidrógeno y C₁₋₃-alquilo; y siendo que el compuesto conforme a la fórmula (1’) no es: (a) N-[1-(piridin-2-il)ciclobutil)-5-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]pirimidin-2-amina; (b) 5-{5-[cloro(difluoro)metil)-1,2,4-oxadiazol-3-il}-N-[1-(piridin-2-il)ciclobutil]pirimidin-2-amina; (c) N-(1-fenilciclopropil)-5-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]pirimidin-2-amina; (d) 5-{5-[cloro(difluoro)metil)-1,2,4-oxadiazol-3-il}-N-(1-fenilciclopropil)pirimidin-2-amina; (e) N-[1-(2-metilpiridin-4-il)etil)-5-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]pirimidin-2-amina. Reivindicación 16: Una composición que comprende al menos un compuesto conforme a la fórmula (1’) conforme a la reivindicación 14 ó 15 y al menos un vehículo apto para uso agrícola.Claim 1: Use of a compound according to formula (1) to control phytopathogenic fungi in plants, where X is fluorine or chlorine; R¹, R² taken independently are selected from the group consisting of hydrogen, cyano, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₂₋₈-alkenyl, C₂₋₈-haloalkenyl, C₂₋₈-alkynyl, C₂₋₈-haloalkynyl, C₃₋₇-carbocyclyl, aryl, 3-10 membered heterocyclyl, heteroaryl, aryl-C₁₋₈-alkyl, 3-10 membered heterocyclyl-C₁₋₈-alkyl, heteroaryl-C₁₋₈- alkyl and C₃₋₇-carbocyclyl-C₁₋₈-alkyl, wherein said acyclic R¹ and R² may be substituted with, respectively, one or more R¹ᵃ and R²ᵃ substituents and said cyclic R¹ and R² may be substituted with, respectively, one or further substituents R¹ᵇ and R²ᵇ, or R¹, R² may form, together with the carbon atom to which they are attached, a C₃₋₇-carbocyclyl or a 3- to 10-membered heterocyclyl, said C₃₋₇-carbocyclyl or heterocyclyl being 3 to 10 members may be substituted with one or more R¹ᵇ substituents; Cy is 3- to 10-membered aryl, heteroaryl, C₃₋₁₀-carbocyclyl or heterocyclyl; n is 0, 1, 2, 3 or 4; R³ taken independently is selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, carboxyl, sulfanyl, pentafluoro-l⁶-sulfanyl, formyl, carbamoyl, carbamate, C₁₋₆-alkyl, C₁₋₆- cyanoalkyl, C₁₋₆-haloalkyl, C₂₋₆-alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₂₋₆-haloalkynyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₁₋₆-alkoxy - ₇-halocarbocyclyl, C₁₋₆-hydroxyalkyl, C₁₋₆-alkylamino, di-C₁₋₆-alkylamino, C₁₋₆-alkylcarbonyl, C₁₋₆-alkoxycarbonyl, C₁₋₆-haloalkoxycarbonyl, C₁₋₆-alkylcarbamoyl, di- C₁₋₆-alkylcarbamoyl, aminocarbonyl, C₁₋₈-alkylcarbonyloxy, C₁₋₈-haloalkylcarbonyloxy, C₁₋₈-alkylcarbonylamino, C₁₋₈-haloalkylcarbonylamino, C₁₋₆-alkylsulfonylamino, C₁₋₆-haloalkylsulfonyl, C₁-amino, sulfamo alkylsulfamoyl, di-C₁₋₈-alkylsulfamoyl, aryl (for example phenyl), aryl-C₁₋₆-alkyl and heteroaryl, wherein said acyclic and cyclic R³ may be substituted with one or more substituents, which may be the same or different, to be selected from the group consisting of halogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy and C₁₋₆-haloalkoxy; R⁴ is selected from the group consisting of hydrogen, hydroxy, formyl, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₂₋₆-alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₂₋₆- haloalkynyl, -C(=O)-C₁₋₆-alkyl, -C(=O)-C₁₋₆-haloalkyl, -C(=S)-C₁₋₆-alkyl, -C(=S)-C₁₋ ₆-haloalkyl, -C(=O)-O-C₁₋₆-alkyl, -C(=O)-O-C₁₋₆-haloalkyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₁₋₆- alkylsulfonyl, C₁₋₆-haloalkylsulfonyl, phenylsulfonyl, C₃₋₁₀-carbocyclyl, 3- to 10-membered heterocyclyl, aryl (phenyl), heteroaryl, C₃₋₁₀-carbocyclyl-C₁₋₆-alkyl, C₃₋₁₋-carbocyclyl- ₆-haloalkyl, aryl-C₁₋₆-alkyl, aryl-C₁₋₆-haloalkyl, heteroaryl-C₁₋₆-alkyl, and heteroaryl-C₁₋₆-haloalkyl, wherein said cyclic and acyclic R⁴ may be substituted with one or more substituents to be selected from the group consisting of halogen, cyano, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy, and C₁₋₆-haloalkoxy; R⁵ is hydrogen or fluorine; R¹ᵃ, R²ᵃ taken independently are selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-l⁶-sulfanyl, formyl, carbamoyl, carbamate, C₃₋₇-cycloalkyl, C₃₋₇- halocycloalkyl, C₁₋₈-alkylamino, di-C₁₋₈-alkylamino, C₁₋₈-alkoxy, C₁₋₈-haloalkoxy, C₁₋₈-alkylsulfanyl, C₁₋₈-haloalkylsulfanyl, C₁₋₈-alkylcarbonyl, C₁₋₈- haloalkylcarbonyl, C₁₋₈-alkylcarbamoyl, di-C₁₋₈-alkylcarbamoyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxycarbonyl, C₁₋₈-alkylcarbonyloxy, C₁₋₈-haloalkylcarbonyloxy, C₁₋₋₈-alkylcarbonylamino, C₁₋₈-alkylcarbonylamino, haloalkylcarbonylamino, C₁₋₈-alkylsulfinyl, C₁₋₈-haloalkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₁₋₈-alkylsulfonylamino, C₁₋₈-haloalkylsulfonylamino, sulfamoyl, C₁₋₁-di- ₈-alkylsulfamoyl; R¹ᵇ, R²ᵇ taken independently are selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, carboxyl, sulfanyl, pentafluoro-l⁶-sulfanyl, formyl, carbamoyl, carbamate, C₁₋₆-alkyl, C₁₋ ₆-Cyanoalkyl, C₁₋₆-haloalkyl, C₂₋₆-alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₂₋₆-haloalkynyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₆₋-₆ C₁₋₆-alkoxy-alkyl, C₁₋₆-alkylsulfanyl, C₁₋₆-haloalkylsulfanyl, C₁₋₈-alkylsulfinyl, C₁₋₈-haloalkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₆-alkyl-C₋( =O)-NH-, C₃₋₇-carbocyclyl, C₃₋₇-halocarbocyclyl, hydroxy-C₁₋₆-alkyl, C₁₋₆-alkylamino, di-C₁₋₆-alkylamino, C₁₋₆-alkylcarbonyl, C₁₋₆ -alkoxycarbonyl, C₁₋₆-haloalkoxycarbonyl, C₁₋₆-alkylcarbamoyl, di-C₁₋₆-alkylcarbamoyl, aminocarbonyl, C₁₋₈-alkylcarbonyloxy, C₁₋₈-haloalkylcarbonyloxy, C₁₋₁-alkylcarbonylamino, C₁₋,halo-alkylcarbonyl ₋₆-alkylsulfonylamino, C₁₋₆-haloalkylsulfonylamino, sulfamoyl, C₁₋₈-alkylsulfamoyl, di-C₁₋₈-alkylsulfamoyl, aryl (for example phenyl), aryl-C₁₋₆-alkyl and heteroaryl, wherein said aryl (phenyl) or heteroaryl is optionally substituted with one or more substituents, which may be the same or different, to be selected from the group consisting of halogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy, and C₁₋₆-haloalkoxy; or an N-oxide salt or solvate of said structure; wherein the compound according to formula (1) is not: (a) N-[1-(pyridin-2-yl)cyclobutyl)-5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3 -yl]pyrimidin-2-amine; (b) 5-{5-[chloro(difluoro)methyl)-1,2,4-oxadiazol-3-yl}-N-[1-(pyridin-2-yl)cyclobutyl]pyrimidin-2-amine; (c) N-(1-phenylcyclopropyl)-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyrimidin-2-amine; (d) 5-{5-[chloro(difluoro)methyl)-1,2,4-oxadiazol-3-yl}-N-(1-phenylcyclopropyl)pyrimidin-2-amine. Claim 13: A method for controlling phytopathogenic fungi comprising the step of applying at least one compound according to formula (1) according to any one of claims 1 to 12 to plants, plant parts, seeds, fruits or the soil in which the plants grow. Claim 14: A compound according to formula (1') or a salt, N-oxide or solvate of said structure; wherein X, R¹, R², R³, R⁴, R⁵, Cy and n are as defined in any of claims 1 to 12, wherein when X is fluorine and R⁴ is hydrogen or C₁₋₆-alkyl, R¹ and R² they are not both hydrogen; with compounds wherein X is fluorine, Cy is phenyl or 6-membered heteroaryl, n is 0 and R¹, R² and R⁴ are selected, each considered independently, from hydrogen and C₁₋₃- I rent; and where the compound according to formula (1') is not: (a) N-[1-(pyridin-2-yl)cyclobutyl)-5-[5-(trifluoromethyl)-1,2,4-oxadiazole -3-yl]pyrimidin-2-amine; (b) 5-{5-[chloro(difluoro)methyl)-1,2,4-oxadiazol-3-yl}-N-[1-(pyridin-2-yl)cyclobutyl]pyrimidin-2-amine; (c) N-(1-phenylcyclopropyl)-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyrimidin-2-amine; (d) 5-{5-[chloro(difluoro)methyl)-1,2,4-oxadiazol-3-yl}-N-(1-phenylcyclopropyl)pyrimidin-2-amine; (e) N-[1-(2-methylpyridin-4-yl)ethyl)-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyrimidin-2-amine. Claim 16: A composition comprising at least one compound according to formula (1') according to claim 14 or 15 and at least one vehicle suitable for agricultural use.

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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018165520A1 (en) 2017-03-10 2018-09-13 Vps-3, Inc. Metalloenzyme inhibitor compounds
JP2023043197A (en) * 2020-03-04 2023-03-29 日本曹達株式会社 Azinyl azole compound and pest control agent
UY39277A (en) * 2020-06-19 2022-01-31 Bayer Ag COMBINATION OF ACTIVE COMPOUNDS, METHOD AND USE OF THE SAME TO CONTROL HARMFUL MICROORGANISMS AND TREATED SEED
UY39854A (en) 2021-07-15 2022-11-30 Kumiai Chemical Industry Co FORMAMIDE DERIVATIVE AND HORTICULTURAL AND AGRICULTURAL CONTROL AGENT FOR THE CONTROL OF DISEASES OF THE

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3639877A1 (en) 1986-11-21 1988-05-26 Bayer Ag HETARYLALKYL SUBSTITUTED 5- AND 6-RINGHETEROCYCLES
CN1255143A (en) 1997-05-09 2000-05-31 阿格拉奎斯特公司 Novel strain of bacillus for controlling plant diseases and corn rootworm
US6245551B1 (en) 1999-03-30 2001-06-12 Agraquest, Inc. Strain of Bacillus pumilus for controlling plant diseases caused by fungi
JP4071036B2 (en) 2001-11-26 2008-04-02 クミアイ化学工業株式会社 Bacillus sp. D747 strain and plant disease control agent and pest control agent using the same
GB0213715D0 (en) 2002-06-14 2002-07-24 Syngenta Ltd Chemical compounds
TWI312272B (en) 2003-05-12 2009-07-21 Sumitomo Chemical Co Pyrimidine compound and pests controlling composition containing the same
GB0414438D0 (en) 2004-06-28 2004-07-28 Syngenta Participations Ag Chemical compounds
KR101310073B1 (en) 2004-10-20 2013-09-24 이하라케미칼 고교가부시키가이샤 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient
JP4871289B2 (en) 2005-10-06 2012-02-08 日本曹達株式会社 Cyclic amine compounds and pest control agents
JP5268461B2 (en) 2008-07-14 2013-08-21 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient
CN101337940B (en) 2008-08-12 2012-05-02 国家农药创制工程技术研究中心 Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity
CN101337937B (en) 2008-08-12 2010-12-22 国家农药创制工程技术研究中心 N-benz-3-substituted amino pyrazoles compounds with insecticidal activity
CN101715774A (en) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 Preparation and use of compound having insecticidal activity
EP2184273A1 (en) 2008-11-05 2010-05-12 Bayer CropScience AG Halogen substituted compounds as pesticides
GB0820344D0 (en) 2008-11-06 2008-12-17 Syngenta Ltd Herbicidal compositions
WO2010066780A1 (en) 2008-12-12 2010-06-17 Syngenta Participations Ag Spiroheterocyclic n-oxypiperidines as pesticides
WO2011085575A1 (en) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 Ortho-heterocyclyl formanilide compounds, their synthesis methods and use
AR081721A1 (en) 2010-02-25 2012-10-17 Nippon Soda Co CYCLING AND ACARICIDE AMINA COMPOUND
KR20130080485A (en) 2010-05-31 2013-07-12 신젠타 파티서페이션즈 아게 Method of crop enhancement
AP3539A (en) 2010-08-31 2016-01-13 Meiji Seika Pharma Co Ltd Pest control agent
CN101967139B (en) 2010-09-14 2013-06-05 中化蓝天集团有限公司 Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof
WO2013050317A1 (en) 2011-10-03 2013-04-11 Syngenta Limited Polymorphs of an isoxazoline derivative
CN102391261A (en) 2011-10-14 2012-03-28 上海交通大学 N-substituted dioxazine compound as well as preparation method and application thereof
WO2013066839A2 (en) * 2011-10-31 2013-05-10 Glaxosmithkline Llc Compounds and methods
AU2012345557A1 (en) 2011-11-28 2014-06-26 Novartis Ag Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease
TWI566701B (en) 2012-02-01 2017-01-21 日本農藥股份有限公司 Arylalkyloxypyrimidine derivatives and agrohorticultural insecticides comprising said derivatives as active ingredients, and method of use thereof
WO2013144213A1 (en) 2012-03-30 2013-10-03 Basf Se N-substituted pyridinylidene compounds and derivatives for combating animal pests
EP2647626A1 (en) 2012-04-03 2013-10-09 Syngenta Participations AG. 1-Aza-spiro[4.5]dec-3-ene and 1,8-diaza-spiro[4.5]dec-3-ene derivatives as pesticides
RU2623233C2 (en) 2012-04-27 2017-06-23 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Pesticidal compositions and methods related thereto
US9282739B2 (en) 2012-04-27 2016-03-15 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
CN103232431B (en) 2013-01-25 2014-11-05 青岛科技大学 Dihalogenated pyrazole amide compound and its use
CN103109816B (en) 2013-01-25 2014-09-10 青岛科技大学 Thiobenzamide compounds and application thereof
WO2014158644A1 (en) 2013-03-13 2014-10-02 Dow Agrosciences Llc Process for the preparation of triaryl rhamnose carbamates
JP6595985B2 (en) 2013-05-23 2019-10-23 シンジェンタ パーティシペーションズ アーゲー Tank mix formulation
CN103265527B (en) 2013-06-07 2014-08-13 江苏省农用激素工程技术研究中心有限公司 Anthranilamide compound as well as preparation method and application thereof
CN103524422B (en) 2013-10-11 2015-05-27 中国农业科学院植物保护研究所 Benzimidazole derivative, and preparation method and purpose thereof
CA2925873A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
WO2015058028A1 (en) 2013-10-17 2015-04-23 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
WO2016005276A1 (en) 2014-07-07 2016-01-14 Bayer Cropscience Aktiengesellschaft Process for preparing fluorinated iminopyridine compounds
WO2016133011A1 (en) 2015-02-17 2016-08-25 日本曹達株式会社 Agrochemical composition
PT3594225T (en) 2015-03-26 2021-12-07 Bayer Cropscience Lp A novel paenibacillus strain, antifungal compounds, and methods for their use
AU2016355949A1 (en) * 2015-11-19 2018-05-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017110862A1 (en) 2015-12-25 2017-06-29 住友化学株式会社 Oxadiazole compound and use thereof
WO2018055135A1 (en) * 2016-09-23 2018-03-29 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
TWI829634B (en) 2017-04-06 2024-01-21 美商富曼西公司 Fungicidal oxadiazoles
CA3086790A1 (en) 2017-12-22 2019-06-27 Bayer Aktiengesellschaft Fungicidal oxadiazoles
CN113473860A (en) * 2018-12-21 2021-10-01 拜耳公司 1, 3, 4-oxadiazoles and derivatives thereof as novel antifungal agents

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