AR119218A1 - OXADIAZOLE FUNGICIDES - Google Patents
OXADIAZOLE FUNGICIDESInfo
- 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
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- haloalkyl
- aryl
- heteroaryl
- carbocyclyl
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 16
- -1 cyano, hydroxy, amino Chemical group 0.000 abstract 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 abstract 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 229910052731 fluorine Inorganic materials 0.000 abstract 4
- 239000011737 fluorine Substances 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 3
- 125000002015 acyclic group Chemical group 0.000 abstract 3
- 125000004122 cyclic group Chemical group 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 abstract 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 abstract 2
- SHQQYGVGAKIMEX-UHFFFAOYSA-N C1(=CC=CC=C1)C1(CC1)NC1=NC=C(C=N1)C1=NOC(=N1)C(F)(F)F Chemical compound C1(=CC=CC=C1)C1(CC1)NC1=NC=C(C=N1)C1=NOC(=N1)C(F)(F)F SHQQYGVGAKIMEX-UHFFFAOYSA-N 0.000 abstract 2
- 241000233866 Fungi Species 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001204 N-oxides Chemical class 0.000 abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000003032 phytopathogenic effect Effects 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 1
- 125000004740 (C1-C6) haloalkylsulfanyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 abstract 1
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- XDOXQQBUPUADQB-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=NC=NO1 XDOXQQBUPUADQB-UHFFFAOYSA-N 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Chemical group 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 abstract 1
- OMPHAFHZEBBOGW-UHFFFAOYSA-N n-[1-(2-methylpyridin-4-yl)ethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyrimidin-2-amine Chemical compound C=1C=NC(C)=CC=1C(C)NC(N=C1)=NC=C1C1=NOC(C(F)(F)F)=N1 OMPHAFHZEBBOGW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002689 soil Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- 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)
- Plural Heterocyclic Compounds (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)
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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- 2020-06-18 BR BR112021025300A patent/BR112021025300A2/en unknown
- 2020-06-18 EP EP20734340.1A patent/EP3986889A1/en active Pending
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| BR112021025300A2 (en) | 2022-02-01 |
| TW202115045A (en) | 2021-04-16 |
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