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AR048229A1 - Derivados de carboxamidas, procedimiento de obtencion y composiciones antimicrobianas. - Google Patents

Derivados de carboxamidas, procedimiento de obtencion y composiciones antimicrobianas.

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Publication number
AR048229A1
AR048229A1 ARP050100372A ARP050100372A AR048229A1 AR 048229 A1 AR048229 A1 AR 048229A1 AR P050100372 A ARP050100372 A AR P050100372A AR P050100372 A ARP050100372 A AR P050100372A AR 048229 A1 AR048229 A1 AR 048229A1
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Argentina
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alkyl
halogen
halogenoalkyl
hydrogen
formula
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ARP050100372A
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Bayer Cropscience Ag
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    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01N47/00—Biocides, 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
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    • A01N47/06—Biocides, 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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Pyridine Compounds (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Procedimiento para la obtencion de estos productos y su empleo para la lucha contra los microorganismos indeseados, así como nuevos productos intermedios y su síntesis. Composiciones antimicrobianas. Reivindicacion 1: Carboxamidas de la formula (1), en la que: R1 significa hidrogeno, alquilo C1-8, alquilsulfinilo C1-6, alquilsulfoniloC1-6, alcoxiC1-4-alquiloC1-4, cicloalquilo C3-8; halogenoalquilo C1-6, halogenoalquilo C1-6, halogenoalquiltio C1-4, halogenoalquilsulfinilo C1-4, halogenoalquilsulfonilo C1-4, halogeno-alcoxi(C1-4)-alquilo(C1-4), halogenocicloalquilo C3-8 con, respectivamente, 1 hasta 9 átomos de fluor, de cloro y/o de bromo; formilo, formil-alquiloC1-3, (alquilo C1-3)carbonil-alquilo(C1-3), (alcoxi C1- 3)carbonil-alquiloC1-3; halogeno-(alquilo C1-3)carbonil-alquiloC1-3, halogeno-(alcoxi C1-3)carbonil-alquiloC1-3 con, respectivamente, 1 hasta 13 átomos de fluor, de cloro y/o de bromo; (alquilo C1-8)carbonilo, (alcoxi C1-8)carbonilo, (alcoxiC1-4- alquiloC1-4)carbonilo, (cicloalquilo C3-8)carbonilo; (halogenoalquilo C1-6)carbonilo, (halogenalcoxi C1-6)carbonilo, (halogeno-alcoxiC1-4-alquiloC1-4)carbonilo, (halogenocicloalquilo C3-8)carbonilo con, respectivamente, 1 hasta 9 átomos de fluor, de cloro y/o de bromo; o -C(=O)C(=O)R2, -CONR3R4 o -CH2NR5R6; R2 significa hidrogeno, alquilo C1-8, alcoxi C1-8, alcoxiC1-4-alquiloC1-4, cicloalquilo C3-8; halogenoalquilo C1-6, halogenalcoxi C1-6, halogeno-alcoxiC1-4-alquiloC1-4, halogenocicloalquilo C3-8 con, respectivamente, 1 hasta 9 átomos de fluor, de cloro y/o bromo; R3 y R4 significan, independientemente entre sí, respectivamente, hidrogeno, alquilo C1-8, alcoxiC1-4-alquiloC1-4, cicloalquilo C3-8; halogenoalquilo C1-8, halogeno-alcoxiC1-4- alquiloC1-4, halogenocicloalquilo C3-8, con, respectivamente, 1 hasta 9 átomos de fluor, de cloro y/o de bromo; R3 y R4 forman, además, junto con el átomo de nitrogeno, con el que están enlazados, un heterociclo saturado con 5 hasta 8 átomos en el anillo sustituido, en caso dado una o varias veces, de forma igual o de formas diferentes por halogeno o por alquilo C1-4, pudiendo contener el heterociclo 1 o 2 heteroátomos más, no contiguos, de la serie formado por oxígeno, azufre o NR7; R5 y R6 significan, independientemente entre sí, hidrogeno, alquilo C1-8, cicloalquilo con C3-8; halogenoalquilo C1-8, halogenocicloalquilo C3-8, con, respectivamente, 1 hasta 9 átomos de fluor, de cloro y/o de bromo; R5 y R6 forman, además, junto con el átomo de nitrogeno, con el que están enlazados, un heterociclo saturado, con 5 hasta 8 átomos en el anillo sustituido, en caso dado una o varias veces, de forma igual o de formas diferentes por halogeno o por alquilo C1-4, pudiendo contener el heterociclo 1 o 2 heteroátomos más, no contiguos, de las serie formada o oxígeno, azufre o NR7; R7 significa hidrogeno o alquilo C1-6; M significa un anillo de fenilo, de piridina o de pirimidina, de piridazina o de pirazina monosustituidos, respectivamente, por R8 o significa un anillo de tiazol sustituido por R8-A; R8 significa hidrogeno, fluor, cloro, metilo, iso-propilo, metiltio o trifluormetilo; R8-A significa hidrogeno, metilo, metiltio o trifluormetilo; L1 significa alquileno C1- 10 (alcanodiilo); Q significa O, S, SO, SO2 o NR9; L2 significa un enlace directo, SiR10R11 o CO; R significa hidrogeno, alquilo C1-8, alcoxi C1-8, alcoxiC1-4-alquiloC1-4, alquiltioC1-4-alquiloC1-4, alquenilo C2-8, alquinilo C2-8, halogenoalquilo C1- 6, halogenoalquenilo C2-6, halogenoalquinilo C2-6 o cicloalquilo C3-6; R9 significan hidrogeno, alquilo C1-8, alcoxiC1-4-alquiloC1-4, alquiltio C1-4, alquiloC1-4-alqueniloC2-8, alquinilo C2-8, halogenoalquilo C1-6, halogenoalquenilo C2-6, halogenoalquinilo C2-6 o cicloalquilo C3-6; R10 y R11 significan, independientemente entre sí, hidrogeno, alquilo C1-8, alcoxi C1-8, alcoxiC1-4-alquiloC1-4, alquiltioC1-4-alquiloC1-4 o halogenoalquilo C1-6; A significa el resto de la formula (2), en la que: R12 significa, hidrogeno, ciano, halogeno, nitro, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, cicloalquilo C3-6, halogenoalquilo C1-4, halogenalcoxi C1-4 o halogenoalquiltio C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno, aminocarbonilo o aminoacarbonil-alquiloC1-4; R13 significa hidrogeno, halogeno, ciano, alquilo C1-4, alcoxi C1-4 o alquiltio C1-4; R14 significa hidrogeno, alquilo C1-4, hidroxi-alquiloC1-4, alquenilo C2-4, cicloalquilo C3-6, alquiltioC1-4-alquiloC1- 4, alcoxiC1-4-alquiloC1-4, halogenoalquilo C1-4, halogenoalquiltioC1-4-alquiloC1-4, halogenalcoxiC1-4-alquiloC1-4 con, respectivamente, 1 hasta 5 átomos de halogeno, o fenilo; o A significa el resto de la formula (3), en la que: R15 y R16 significan, independientemente entre sí, hidrogeno, halogenoalquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R17 significa halogeno, ciano o alquilo C1-4, o halogenoalquilo C1-4 o halogenalcoxi C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (4), en la que: R18 y R19 significan, independientemente entre sí, hidrogeno, halogenoalquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R20 significa hidrogeno, halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (5), en la que: R21 significa hidrogeno, halogeno, hidroxi, ciano, alquilo C1-6, halogenoalquilo C1-4, halogenalcoxi C1-4 o halogenoalquiltio C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (6), en la que: R22 significa halogeno, hidroxi, ciano, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, halogenoalquilo C1-4, halogenoalquiltio C1-4 o halogenalcoxi C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno; R23 significa hidrogeno, halogeno, ciano, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, halogenoalquilo C1-4, halogenalcoxi C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o A significa el resto de la formula (7), en la que: R24 significa alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R25 significa alquilo C1-4; Q1 significa S(azufre), SO, SO2 o CH2; P significa 0, 1 o 2, significando R25 restos idénticos o diferentes, cuando p signifique 2; o A significa el resto de la formula (8), en la que: R26 significa alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (9), en la que: R27 significa alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (10), en la que: R28 y R29 significan, independientemente entre sí hidrogeno, halogeno, amino, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R30 significa hidrogeno, halogeno, alquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (11), en la que: R31 y R32 significan, independientemente entre sí hidrogeno, halogeno, amino, nitro, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R33 significa hidrogeno, halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (12), en la que: R34 significa hidrogeno, halogeno, amino, alquilamino C1-4, di-(alquilo C1-4)amino, ciano, alquilo C1-4 o halogenoalquilo C1-4 con hasta 5 átomos de halogeno; R35 significa halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (13), en la que: R36 significa hidrogeno, halogeno, amino, alquilamino C1-4, di-(alquilo C1-4)amino, ciano, alquilo C1-4 o halogenoalquilo C1-4 con hasta 5 átomos de halogeno; R37 significa halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (14), en la que: R38 significa halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (15), en la que: R39 significa hidrogeno o alquilo C1-4; R40 significa halogeno o alquilo C1-4; o A significa el resto de la formula (16), en la que: R41 significa alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (17), en la que: R42 significa hidrogeno, halogeno, alquilo C1-4 o halogenoalquilo C1-4 con hasta 5 átomos de halogeno; o A significa el resto de la formula (18), en la que: R43 significa halogeno, hidroxi, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, halogenoalquilo C1-4, halogenoalquiltio C1-4 o halogenalcoxi C1-4 con, respectivamente, 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (19), en la que: R44 significa hidrogeno, ciano, alquilo C1-4, halogenoalquilo C1-4 con hasta 5 átomos de halogeno, alcoxiC1-4-alquiloC1-4, hidroxi-alquiloC1-4, alquilsulfonilo C1-4, di(alquilo C1-4)aminosulfonilo, alquilcarbonilo C1-6 o significa fenilsulfonilo o Benzoilo substituidos respectivamente en caso dado; R45 significa hidrogeno, halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R46 significa hidrogeno, halogeno, ciano, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; R47 significa hidrogeno, halogeno, alquilo C1-4 o halogenoalquilo C1-4 con 1 hasta 5 átomos de halogeno; o A significa el resto de la formula (20), en la que: R48 significa alquilo C1-4.
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