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AR070228A1 - Derivados de 5-fluoro pirimidina - Google Patents

Derivados de 5-fluoro pirimidina

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Publication number
AR070228A1
AR070228A1 ARP090100193A ARP090100193A AR070228A1 AR 070228 A1 AR070228 A1 AR 070228A1 AR P090100193 A ARP090100193 A AR P090100193A AR P090100193 A ARP090100193 A AR P090100193A AR 070228 A1 AR070228 A1 AR 070228A1
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AR
Argentina
Prior art keywords
alkyl
optionally substituted
phenyl
benzyl
haloalkyl
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ARP090100193A
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English (en)
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Dow Agrosciences Llc
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    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • A01N47/18Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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    • A01N47/40Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
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    • A01N47/00Biocides, 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
    • A01N47/40Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44Guanidine; Derivatives thereof
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    • A01NPRESERVATION 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
    • A01N57/00Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
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    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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  • Organic Chemistry (AREA)
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  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La presente se refiere al campo de las 5-fluoro pirimidinas y a los derivados de las mismas y al uso de estos compuestos como fungicidas. Composiciones fungicidas y método de control o prevencion de un ataque fungico a una planta. Reivindicacion 1: Un compuesto de la formula 1 en donde R1 es -N(R3)R4; R2 es -OR21; R3 es H, alquilo C1-6 opcionalmente sustituido con 1-3 R5, alquenilo C2-6 opcionalmente sustituido con 1-3 R5, un anillo heteroaromático de 5 o 6 miembros seleccionado a partir del grupo formado por furanilo, piridinilo, piridinil-N-oxido, pirimidinilo, piridazinilo, pirazinilo, tiazolilo, triazinilo, tiadiazolilo, oxazolilo, isoxazolilo, triazolilo, en donde cada anillo heteroaromático es opcionalmente sustituido con 1-3 R30; imidazol fusionado con un anillo aromático o heteroaromático seleccionado entre el grupo formado por benceno, oxazol, isoxazol, furan, tiazol, pirimidina, piridina, pirrol, pirazina, tiofeno, en donde cada anillo aromático heteroaromático es opcionalmente sustituido con 1-3 R30; benzo[1,3]dioxolilo; 3H-isobenzofuran-1-onilo; ciano; alquinilo C3-6 opcionalmente sustituido con 1-3 R5, -C(=O)R6; -C(=S)NHR8 , -OR7; -P(O)(OR15)2; -S(O)2R8, -SR8, -Si(R8)3, -N(R9)R10; -N=C(R15)R16; -(CHR22)mR23; -(CHR24)OR29; -C(=O)N(R8)R10; en donde m es un entero de 1-3; R4 es alquilo C1-6, opcionalmente sustituido con 1-3 R5; o -C=O(R6); -C(=O)N(R8)R10; alternativamente R3 y R4 pueden tomarse juntos para formar: un anillo saturado o insaturado de 5 o 6 miembros que contiene 1-3 heteroátomos en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R11; =C(R12)N(R13)R14; =C(R13)(R14); o =C(R15)OR15; R5 es independientemente halogeno, alquilo C1-6, haloalquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, alquiltio C1-4, haloalquiltio C1-4, amino, alquilamino C1-3, alcoxicarbonilo C2-6, alquilcarbonilo C2-6, alquilaminocarbonilo C2-6, -OH, N-metil piperazina o trialquilsililo C3-6; R6 es independientemente H, alquilo C1-6, haloalquilo C1-5, alcoxi C1-5, alcoxicarbonilo C2-6; alquilaminocarbonilo C2-6; 1-benzo[1,2,3]tiadiazol-7-ilo, tiazolilo, bencilo, fenilo, fenoxi , o benciloxi en donde tiazol, bencilo, fenilo, fenoxi, o benciloxi pueden ser opcionalmente sustituidos con 1-3 R20; R7 es H, alquilo C1-6, alquenilo C2-6, haloalquilo C1-5, bencilo que pueden ser opcionalmente sustituidos con 1-5 R20, un anillo saturado o insaturado de 5 o 6 miembros que contiene 1-3 heteroátomos en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R11, o CHR18C(O)OR19; R8 es alquilo C1-6, haloalquilo C1-6, o fenilo opcionalmente sustituido con 1-3 R20; R9 es H, alquil C1-6-haloalquilo C1-6, o fenilo opcionalmente sustituido con 1-3 R20, o -C(=O)R17; R10 es H o alquilo C1-6; haloalquilo C1-6, o fenilo opcionalmente sustituido con 1-3 R20; R11 es independientemente halogeno, alquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, amino, alquilamino C1-6, dialquilamino C2-6, alcoxicarbonilo C2-6, o alquilcarbonilo C2-6; R12 es H o alquilo C1-4; R13 y R14 son independientemente H, ciano, -OH, alquilo C1-4, alcoxi C1-6, alquilcarbonilo C2-6, fenilo, o bencil en donde el fenilo o bencilo pueden ser opcionalmente sustituidos con 1-3 R20; alternativamente R13 y R14 pueden tomarse conjuntamente para formar: un anillo saturado o insaturado de 5 o 6 miembros que contiene 1-3 heteroátomos en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R11, o 3,4-dihidro-1H-isoquinolin-2-ilo; R15 es H o alquilo C1-6; R16 es H, alquilo C1-6, fenilo opcionalmente sustituido con 1-3 R20, alternativamente R15 y R16 pueden tomarse conjuntamente como -(CH2)4- o -(CH2)5-; R17 es H, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, fenilo, fenoxi , o benciloxi en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R20; R18 es H, alquilo C1-6, o haloalquilo C1-6; R19 es H, alquilo C1-6, haloalquilo C1-6, o bencilo; R20 es independientemente halogeno, ciano, nitro, amino, alcoxialcoxi C1-6, alquilo C1-6, haloalquilo C1-6, hidroxi C1-6 alquilo, alcoxialquilo C2-6, haloalcoxialquilo C2-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C3-6, haloalquiniloxi C3-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, alqueniltio C2-6, haloalqueniltio C2-6, haloalquenilsulfonilo C2-6, alquiniltio C3-6, alquinilsulfonilo C3-6, haloalquinilsulfonilo C3-6, alquilamino C1-6, dialquilamino C2-8, dialquilaminocarbonilo C3-8, trialquilsililo C3-6, 2-[(E)-metoxi imino]-N-metil-acetamidilo, fenilo, bencilo, benciloxi, fenoxi, un anillo heteroaromático de 5 o 6 miembros, en donde cada fenilo, bencilo, benciloxi, fenoxi, o anillo heteroaromático de 5 o 6 miembros puede ser opcionalmente sustituido con 1-3 sustituyentes independientemente seleccionados entre R31; R21 es H, alquilo C1-14; haloalquilo C1-6; alquenilo C2-4; haloalquenilo C2-4; alquinilo C3-4, haloalquinilo C3-4; fenilo, naftilo, o tetrahidroquinolinilo en donde cada uno es opcionalmente sustituido con 1-3 R20; -(CHR22)mR23; -(CHR24)mC(O)OR25; -(CHR24)mC(O)R26; -(CHR24)mC(O)N(R27)R28; -(CHR24)mOR29; -(CHR24)mSR29, -(CHR24)mN(R27)R28, -C(=O)R32; -N=C(R24)(R32); -Si(R8)3; -SO2R33; alcoxi C2-6 carbonilo; alquilaminocarbonilo C2-6, alquilcarbonilo C2-6; azucares seleccionados entre el grupo formado por beta-D-glucosa- tetraacetato, ramnosa, fructosa, y pentosa; o un anillo heteroaromático de 5 o 6 miembros que incluye furanilo, piridinilo, piridinil-N-oxido, pirimidinilo, piridazinilo, pirazinilo, pirazolilo, tiazolilo, triazinilo, tiadiazolilo, oxazolilo, triazolilo o isoxazolilo en donde cada anillo heteroaromático de 5 o 6 miembros puede ser opcionalmente sustituido con 1 a 5 R20; R22 es independientemente H; halogeno; ciano; nitro; alquilo C1-6, haloalquilo C1-6; fenilo o bencilo opcionalmente sustituido con 1-3 R20; hidroxi C1-6 alquilo; alcoxialquilo C2-6; haloalquinilo C3-6; alquenilo C2-6, haloalquenilo C2-6; alquinilo C3-6; alcoxi C1-6; haloalcoxi C1-6, alquiltio C1-6, alquilamino C1-6; dialquilamino C2-8; cicloalquilamino C3-6; alquil C4-6 cicloalquilamino; alquilcarbonilo C2-6, alcoxicarbonilo C2-6; alquilaminocarbonilo C2-6; dialquilaminocarbonilo C3-8; trialquilsililo C3-6; benzo[ 1,3]dioxolilo; anillos heteroaromáticos de anillo fusionado seleccionados entre el grupo formado por benzotiofenilo, quinolinilo, isoquinolinilo, tieno[2,3-b]piridilo, 1-metil-1H-tieno[2,3-c]pirazolilo, y benzoimidazolilo, en donde cada uno de los anillos puede ser además sustituido con 1 a 3 R20; o un anillo heteroaromático de 5 o 6 miembros seleccionado entre el grupo formado por furanilo, piridinilo, piridinil-N-oxido, pirimidinilo, piridazinilo, pirazinilo, tiazolilo, triazinilo, tiadiazolilo, oxazolilo, isoxazolilo, triazolilo o tienilo; R23 es H; halogeno; alquilo C1-6; haloalquilo C1-6; dialquilamino C2-6; fenilo opcionalmente sustituido con 1 a 5 R20; anillo heteroaromáticos de anillo fusionado seleccionados entre el grupo formado por benzotiofenilo, quinolinilo, isoquinolinilo, tieno[2,3-b]piridilo, 1-metil-1H-tieno[2,3-c]pirazolilo, benzofuranil y benzoimidazolilo, en donde cada uno de los anillos puede ser además sustituido con 1 a 3 R20; naftalilo; pirrolidinonilo; oxetanilo; alquiltio C1-6 opcionalmente sustituido con 1 a 5 R20; un anillo saturado o insaturado de 5 o 6 miembros que contiene 1-3 heteroátomos en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R11, o un anillo heteroaromático de 5 o 6 miembros seleccionado entre el grupo formado por furanilo, piridinilo, piridinil-N-oxido, pirimidinilo, piridazinilo, pirazinilo, pirazolilo, tiazolilo, triazinilo, tiadiazolilo, oxazolilo, isoxazolilo, triazolilo, imidazolilo, tiofeno-2-ilo y tiofen-3-ilo en donde cada anillo heteroaromático puede ser opcionalmente sustituido con 1 a 3 R20; R24 es H, alquilo C1-6, alcoxi C1-6, bencilo, o fenilo en donde cada uno, entre bencilo o fenilo pueden ser opcionalmente sustituidos con 1-3 R20; R25 es H, alquilo C1-6, o bencil opcionalmente sustituido con 1-3 R20; R26 es H; alquilo C1-6, alcoxi C1-6; fenilo opcionalmente sustituido con 1-3 R20; o un anillo heteroaromático de 5 o 6 miembros que incluye furanilo, piridinilo, piridinil-N-oxido, pirimidinilo, piridazinilo, pirazinilo, tiazolilo, triazinilo, tiadiazolilo, oxazolilo, triazolilo o isoxazolilo; R27 y R28 son independientemente H, alquilo C1-6; bencilo, o fenilo en donde cada uno entre bencilo o fenilo puede ser opcionalmente sustituido con 1-3 R20 o un anillo saturado o insaturado de 5 o 6 miembros que contiene 1-3 heteroátomos en donde cada anillo puede ser opcionalmente sustituido con 1 a 3 R11; R29 es H, alquilo C1-6, alcoxialquilo C1-6, alquilcarbonilo, bencilo, o fenilo en donde cada uno entre bencil o fenilo puede ser opcionalmente sustituido con 1-3 R20; y R30 es independientemente halogeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, hidroxi C1-6 alquilo, alcoxialquilo C2-6, haloalcoxialquilo C2-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C3-6, haloalquiniloxi C3-6, alquiltio C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, alqueniltio C2-6, haloalqueniltio C2-6, haloalquenilsulfonilo C2-6, alquiniltio C3-6, alquinilsulfonilo C3-6, haloalquinilsulfonilo C3-6, alquilamino C1-6, dialquilamino C2-8, dialquilaminocarbonilo C3-8, trialquilsililo C3-6, tiazolilo, fenilo, pirimidinilo en donde el tiazolilo, fenilo, o pirimidinilo puede ser opcionalmente sustituido con 1 a 3 R20; R31 es independientemente halogeno, ciano, nitro, alquilo C1-6, haloalquilo C1-6, hidroxi C1-6 alquilo, alcoxialquilo C2-6, haloalcoxialquilo C2-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C3-6, haloalquinilo C3-6, hidroxilo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C3-6, haloalquiniloxi C3-6, alquilt
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