ES2558166T3 - Compuestos de N-tio-antranilamida y su uso como pesticidas - Google Patents

Compuestos de N-tio-antranilamida y su uso como pesticidas Download PDF

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ES2558166T3
ES2558166T3 ES12750733.3T ES12750733T ES2558166T3 ES 2558166 T3 ES2558166 T3 ES 2558166T3 ES 12750733 T ES12750733 T ES 12750733T ES 2558166 T3 ES2558166 T3 ES 2558166T3
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cyclopropyl
alkoxy
alkyl
group
radicals
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Florian Kaiser
Karsten KÖRBER
Prashant Deshmukh
Deborah L. Culbertson
Paul Neese
Koshi Gunjima
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BASF SE
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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Un compuesto de la formula general (I)**Fórmula** en donde R1 se selecciona del grupo que consiste de halógeno y halometilo; R2 se selecciona del grupo que consiste de hidrógeno, halógeno, halometilo y ciano; R3 se selecciona de hidrógeno, C1-C6 alquilo, C1-C6 haloalquilo, C2-C6-alquenilo, C2-C6-haloalquenilo, C2-C6-alquinilo, C2-C6-haloalquinilo, C3-C8-cicloalquilo, C3-C8-halocicloalquilo, C1-C4-alcoxi-C1-C4-alquilo, C1-C4-haloalcoxi- C1-C4- alquilo, C(>=O)Ra, C(>=O)ORb y C(>=O)NRcRd; R4 es halógeno; R5, R6 se seleccionan independientemente uno de otro del grupo que consiste de hidrógeno, C1-C10-alquilo, C3-C8- cicloalquilo, C2-C10-alquenilo, C2-C10-alquinilo, en donde los radicales alifáticos y cicloalifáticos antes mencionados pueden ser sustituidos con 1 a 10 sustituyentes Re, y fenilo, que es no sustituido o lleva 1 a 5 sustituyentes RF; o R5 y R6 juntos representan una cadena de C2-C7-alquileno, C2-C7-alquenileno o C6-C9-alquinileno que forman junto con el átomo de azufre al que están unidos un anillo de 3-, 4-, 5-, 6-, 7-, 8-, 9 o 10- miembros saturado, parcialmente insaturado o totalmente insaturado, en donde 1 a 4 de los grupos CH2 en la cadena de C2-C7-alquileno o 1 a 4 de cualquiera de los grupos CH2 o CH en la cadena de C2-C7-alquenileno o 1 a 4 de cualquiera de los grupos CH2 en la cadena de C6-C9-alquinileno puede ser reemplazado por 1 a 4 grupos seleccionados independientemente del grupo que consiste de C>=O, C>=S, O, S, N, NO, SO, SO2 y NH, y en donde los átomos de carbono y/o nitrógeno en la cadena de C2-C7-alquileno, C2-C7-alquenileno o C6-C9-alquinileno pueden ser sustituidos con 1 a 5 sustituyentes seleccionados independientemente del grupo que consiste de halógeno, ciano, C1-C6-alquilo, C1-C6-haloalquilo, C1- C6-alcoxi, C1-C6-haloalcoxi, C1-C6-alquiltio, C1-C6-haloalquiltio, C3-C8-cicloalquilo, C3-C8-halocicloalquilo, C2-C6- alquenilo, C2-C6-haloalquenilo, C2-C6-alquinilo y C2-C6-haloalquinilo; siendo dichos sustituyentes idénticos o diferentes el uno del otro si más de un sustituyente está presente; Ra se selecciona del grupo que consiste de C1-C6-alquilo, C2-C6-alquenilo, C2-C6-alquinilo, C3-C8-cicloalquilo, C1-C6- alcoxi, C1-C6-alquiltio, C1-C6-alquilsulfinilo, C1-C6-alquilsulfonilo, en donde uno o más grupos CH2 de los radicales antes mencionados pueden ser reemplazados por un grupo C>=O, y/o las unidades estructurales alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden llevar 1 o 2 sustituyentes seleccionados de C1-C4 alcoxi; fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales pueden ser no sustituido, parcial o totalmente halogenados y/o llevar 1, 2 o 3 sustituyentes seleccionados de C1-C6-alquilo, C1-C6-haloalquilo, C1-C6-alcoxi, C1-C6- haloalcoxi, (C1-C6-alcoxi)carbonilo, C1-C6-alquilamino y di-(C1-C6-alquil)amino, Rb se selecciona del grupo que consiste de C1-C6-alquilo, C2-C6-alquenilo, C2-C6-alquinilo, C3-C8-cicloalquilo, C1-C6- alcoxi, C1-C6-alquiltio, C1-C6-alquilsulfinilo, C1-C6-alquilsulfonilo, en donde uno o más grupos CH2 de los radicales antes mencionados pueden ser reemplazados por un grupo C>=O, y/o las unidades estructurales alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden llevar 1 o 2 sustituyentes seleccionados de C1-C4-alcoxi; fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales pueden ser no sustituido, parcial o totalmente halogenados y/o llevar 1, 2 o 3 sustituyentes seleccionados de C1-C6-alquilo, C1-C6-haloalquilo, C1-C6-alcoxi, C1-C6- haloalcoxi y (C1-C6-alcoxi)carbonilo; Rc, Rd son, independientemente uno de otro e independientemente de cada ocurrencia, seleccionados del grupo que consiste de hidrógeno, ciano, C1-C6-alquilo, C2-C6-alquenilo, C2-C6-alquinilo, C3-C8-cicloalquilo, en donde uno o más grupos CH2 de los radicales antes mencionados pueden ser reemplazados por un grupo C>=O, y/o las unidades estructurales alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, parcial o totalmente halogenadas y/o pueden llevar 1 o 2 radicales seleccionados de C1-C4-alcoxi; C1-C6-alcoxi, C1-C6-haloalcoxi, C1-C6-alquiltio, C1-C6-alquilsulfinilo, C1-C6- alquilsulfonilo, C1-C6-haloalquiltio, fenilo, bencilo, piridilo y fenoxi, en donde los últimos cuatro radicales mencionados pueden ser no sustituidos, parcial o totalmente halogenados y/o llevar 1, 2 o 3 sustituyentes seleccionados de C1-C6- alquilo, C1-C6-haloalquilo, C1-C6-alcoxi, C1-C6 haloalcoxi y (C1-C6-alcoxi)carbonilo; o Rc y Rd, junto con el átomo de nitrógeno al que están unidos, pueden formar un anillo heterocíclico de 3, 4, 5, 6 o 7 miembros saturados parcialmente insaturados o totalmente insaturados que puede contener adicionalmente 1 o 2 heteroátomos adicionales o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros de anillo, donde el anillo heterocíclico puede ser opcionalmente sustituido con halógeno, C1-C4-haloalquilo, C1-C4-alcoxi o C1-C4-haloalcoxi; Re es independientemente seleccionados del grupo que consiste de halógeno, ciano, nitro, -OH, -SH, -SCN, C1-C6- alquilo, C2-C6-alquenilo, C2-C6-alquinilo, C3-C8-cicloalquilo, en donde uno o más grupos CH2 de los radicales antes mencionados pueden ser reemplazados por un grupo C>=O, y/o las unidades estructurales alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituido, parcial o totalmente halogenados y/o pueden llevar 1 o 2 radicales seleccionados de C1-C4-alcoxi; C1-C6-alcoxi, C1-C6-haloalcoxi, C1-C6-alquiltio, C1-C6-alquilsulfinilo, C1-C6- alquilsulfonilo, C1-C6-haloalquiltio, -ORa, -NRcRd, -S(O)nRa, -S(O)nNRcRd, -C(>=O)Ra, -C(>=O)NRcRd, -C(>=O)ORb, - C(>=S)Ra, -C(>=S)NRcRd, -C(>=S)ORb, -C(>=S)SRb, -C(>=NRc)Rb, -C(>=NRc)NRcRd, fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales pueden ser no sustituido, parcial o totalmente halogenados y/o llevar 1, 2 o 3 sustituyentes seleccionados de C1-C6-alquilo, C1-C6-haloalquilo, C1-C6-alcoxi y C1-C6-haloalcoxi; o dos radicales vecinales Re juntos forman un grupo >=O, >=CH(C1-C4-alquil), >=C(C1-C4-alquil)C1-C4-alquilo, >=N(C1-C6-alquil) o >=NO(C1- C6-alquil); RF es independientemente seleccionados del grupo que consiste de halógeno, ciano, nitro, -OH, -SH, -SCN, C1-C6- alquilo, C2-C6-alquenilo, C2-C6-alquinilo, C3-C8-cicloalquilo, en donde uno o más grupos CH2 de los radicales antes mencionados pueden ser reemplazados por un grupo C>=O, y/o las unidades estructurales alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituido, parcial o totalmente halogenados y/o pueden llevar 1 o 2 radicales seleccionados de C1-C4 alcoxi; C1-C6-alcoxi, C1-C6-haloalcoxi, C1-C6-alquiltio, C1-C6-alquilsulfinilo, C1-C6- alquilsulfonilo, C1-C6-haloalquiltio, -ORa, -NRcRd, -S(O)nRa, -S(O)nNRcRd,- C(>=O)Ra, -C(>=O)NRcRd, -C(>=O)ORb, - C(>=S)Ra, -C(>=S)NRcRd, -C(>=S)ORb, -C(>=S)SRb, -C(>=NRc)Rb, y -C(>=NRc)NRcRd; k es 0 o 1; n es 0, 1 o 2; o un estereoisómero, sal, tautómero o N-óxido del mismo.

Description

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Ej.
R1 R2 R5 R6 HPLC-MS: Rt(min) y [M + H]
S.3
Cl Cl -CH2-CH2-CH2-CH2 3.543 (columna 1) 564.00
S.4
Cl Cl -CH2-S-CH2-CH2 3.613 (columna 1) 583.85
S.5
Cl Cl CH3 CH3 3.372 (columna 1) 539.95
S.6
Cl Cl CH2CH3 CH2CH3 3.496 (columna 1) 567.90
S.7
Cl Cl CH(CH3)2 CH2CH3 1.303 (columna 2) 581.8
S.8
Cl Cl ciclopropilo CH2CH3 1.253 (columna 2) 578.1
S.9
Cl Cl CH2CH(CH3)2 CH2CH(CH3)2 1.408 (columna 2) 623.8
S.10
Cl Cl ciclopropilo CH(CH3)2 1.284 (columna 2) 593.9
S.11
Cl Cl CH2-c-Pr CH2-c-Pr 1.518 (columna 2) 620.0
S.12
Cl Cl CH2-c-Pr Et 3.704 (columna 1) 594.0
S.13
Cl Cl n-Pr n-Pr 3.981 (columna 1) 595.95
S.14
Br Cl i-Pr i-Pr 3.630 (columna 1) 639.90
S.15
Cl Br i-Pr i-Pr 3.710 (columna 1) 639.90
S.16
CF3 Cl i-Pr i-Pr 1.169 (columna 2) 628.1
S.17
Br Br Et Et 1.218 (columna 2) 655.9
S.18
Cl Cl CH2-c-Pr i-Pr 3.993 (columna 1) 607.95
S.19
Br Cl Et Et 3.633 (columna 1) 611.85
S.20
Cl Br Et Et 3.704 (columna 1) 611.85
S.21
Br Br i-Pr i-Pr 3.665 (columna 1) 683.90
S.22
Cl Cl i-Pr 2-Me-3-Bu 1.409 (columna 2) 623.9
S.23
CF3 Br Et Et 1.248 (columna 2) 645.9
S.24
CF3 Br i-Pr i-Pr 1.308 (columna 2) 673.9
S.25
CF3 Cl Et Et 1.231 (columna 2) 600.0
S.26
Cl Cl i-Pr CH(CH3)-c-Pr 1.263 (columna 2) 553.9
S.27
Br CF3 Et Et 1.301 (columna 2) 646.1
S.28
Br CF3 i-Pr i-Pr 1.350 (columna 2) 674
S.29
Cl CN i-Pr i-Pr 1.262 (columna 2) 585.3
S.30
Cl CF3 Et Et 1.284 (columna 2) 600.1
S.31
Cl CF3 i-Pr i-Pr 1.358 (columna 2) 628.1
S.32
Cl Cl 3-Me-2-Bu 3-Me-2-Bu 1.488 (columna 2) 652.1
S.33
Cl Cl 3-Me-2-Bu Et 1.351 (columna 2) 610
S.34
Cl CN Et Et 1.171 (columna 2) 557.3
S.35
Cl CN CH2-c-Pr CH2-c-Pr 1.287 (columna 2) 609.1
S.36
Cl CN CH2-c-Pr Et 1.236 (columna 2) 583.2
S.37
Cl CN CH2-c-Pr i-Pr 1.271 (columna 2) 597.1
S.38
Cl Cl n-Pe n-Pe 1.508 (columna 2) 652.1
S.39
Cl Cl 3-Me-1-Bu 3-Me-1-Bu 1.489 (columna 2) 652.1
S.40
Cl Cl CH2-c-Bu CH2-c-Bu 1.449 (columna 2) 648.1
S.41
Cl Cl Et CH2-c-Bu 1.344 (columna 2) 607.9
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Claims (7)

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    fila
    R1 R2 R5 R6
    14
    Cl Cl CH(CH3)2 CH(CH3)2
    15
    Br Cl C2H5 C2H5
    16
    Br Cl CH(CH3)2 CH(CH3)2
    17
    Br Br C2H5 C2H5
    18
    Br Br CH(CH3)2 CH(CH3)2
    19
    CF3 Cl C2H5 C2H5
    20
    CF3 Cl CH(CH3)2 CH(CH3)2
    21
    CF3 Br C2H5 C2H5
    22
    CF3 Br CH(CH3)2 CH(CH3)2
    23
    Br CF3 C2H5 C2H5
    24
    Br CF3 CH(CH3)2 CH(CH3)2
    25
    Cl CF3 C2H5 C2H5
    26
    Cl CF3 CH(CH3)2 CH(CH3)2
    27
    Cl CN C2H5 C2H5
    28
    Cl CN CH(CH3)2 CH(CH3)2
    29
    Cl Cl CH2CH(CH3)2 CH2CH(CH3)2
    30
    Cl CN CH2CH(CH3)2 CH2CH(CH3)2
    31
    Br Cl CH2CH(CH3)2 CH2CH(CH3)2
    32
    Br Br CH2CH(CH3)2 CH2CH(CH3)2
    33
    CF3 Cl CH2CH(CH3)2 CH2CH(CH3)2
    34
    CF3 Br CH2CH(CH3)2 CH2CH(CH3)2
    35
    Cl Cl CH(CH3)2 C2H5
    36
    Cl CN CH(CH3)2 C2H5
    37
    Br Cl CH(CH3)2 C2H5
    38
    Br Br CH(CH3)2 C2H5
    39
    CF3 Cl CH(CH3)2 C2H5
    40
    CF3 Br CH(CH3)2 C2H5
    41
    Cl Cl ciclopropilo C2H5
    42
    Cl CN ciclopropilo C2H5
    43
    Br Cl ciclopropilo C2H5
    44
    Br Br ciclopropilo C2H5
    45
    CF3 Cl ciclopropilo C2H5
    46
    CF3 Br ciclopropilo C2H5
    47
    Cl Cl ciclopropilo CH(CH3)2
    48
    Cl CN ciclopropilo CH(CH3)2
    49
    Br Cl ciclopropilo CH(CH3)2
    50
    Br Br ciclopropilo CH(CH3)2
    51
    CF3 Cl ciclopropilo CH(CH3)2
    52
    CF3 Br ciclopropilo CH(CH3)2
    66
    fila
    R1 R2 R5 R6
    53
    Cl Cl -CH2-S-CH2-CH2
    54
    Cl CN -CH2-S-CH2-CH2
    55
    Br Cl -CH2-S-CH2-CH2
    56
    Br Br -CH2-S-CH2-CH2
    57
    CF3 Cl -CH2-S-CH2-CH2
    58
    CF3 Br -CH2-S-CH2-CH2
    59
    Cl Cl CH2-ciclopropilo CH2-ciclopropilo
    60
    Cl Cl CH2-ciclopropilo C2H5
    61
    Cl Cl CH2CH2CH3 CH2CH2CH3
    62
    Cl Br CH(CH3)2 CH(CH3)2
    63
    Cl Cl CH2-ciclopropilo i-Pr
    64
    Cl Br C2H5 C2H5
    65
    Cl Cl CH(CH3)2 CH(CH3)CH(CH3)2
    66
    Cl Cl CH(CH3)2 CH(CH3)-c-Pr
    67
    Cl Cl CH(CH3)CH(CH3)2 CH(CH3)CH(CH3)2
    68
    Cl Cl CH(CH3)CH(CH3)2 C2H5
    69
    Cl CN CH2-ciclopropilo CH2-ciclopropilo
    70
    Cl CN CH2-ciclopropilo C2H5
    71
    Cl CN CH2-ciclopropilo CH(CH3)2
    72
    Cl Cl CH2(CH2)3CH3 CH2(CH2)3CH3
    73
    Cl Cl CH2CH2CH(CH3)2 CH2CH2CH(CH3)2
    74
    Cl Cl CH2-ciclobutilo CH2-ciclobutilo
    75
    Cl Cl C2H5 CH2-ciclobutilo
    76
    Cl Cl CH2(CH2)4CH3 CH2(CH2)4CH3
    77
    Cl Cl CH2CH(C2H5)(CH2)3CH3 CH2CH(C2H5)(CH2)3CH3
    78
    Cl Cl CH2CH2OH CH2CH2OH
    79
    Cl Cl CH2CH2-ciclopropilo CH2CH2-ciclopropilo
    80
    Cl Cl CH2CH2-ciclopropilo i-Pr
    81
    Cl Cl CH2CH2-ciclopropilo C2H5
    82
    Cl Cl CH2-ciclobutilo CH(CH3)2
    83
    Cl Cl CH2-ciclopentilo CH2-ciclopentilo
    84
    Cl Cl CH2-ciclopentilo C2H5
    85
    Cl Cl CH2-ciclopentilo CH(CH3)2
  2. 8.
    El compuesto de fórmula I de acuerdo con la reivindicación 1, que es 2-(3-cloro-2-piridil)-N-[2,4-dicloro-6-[(dietilλ4-sulfaniliden)carbamoil]fenil]-5-(trifluorometil)pirazol-3-carboxamida.
  3. 9.
    Una forma cristalina del compuesto de la reivindicación 8, que en un difractograma de polvo de rayos X a 25ºC y radiación Cu-Kα, muestra al menos cuatro de los siguientes reflejos, dados como valores 2θ: 8.07, 9.53, 11.00, 12.40, 14.31, 16.65, 18.97, 21.14, 21.48, 22.48.
  4. 10.
    Una combinación plaguicida que comprende al menos un compuesto de la fórmula I de acuerdo con cualquiera de las reivindicaciones 1 a 9 y al menos un compuesto activo, seleccionado del grupo que consiste de insecticidas, acaricidas, fungicidas, herbicidas, reguladores del crecimiento de las plantas, aseguradores y nematicidas.
  5. 11.
    Una composición agrícola o veterinaria que comprende al menos un compuesto como se define en una
    67
    5 cualquiera de las reivindicaciones 1 a 9 o la combinación plaguicida de la reivindicación 10 y al menos un vehículo líquido y/o sólido.
  6. 12. Semilla que comprende un compuesto como se define en una cualquiera de las reivindicaciones 1 a 9 o una combinación pesticida de la reivindicación 10 en una cantidad de 0.1 g a 10 kg por 100 kg de material de propagación de las plantas.
    10 13. Uso no terapéutico de un compuesto como se define en una cualquiera de las reivindicaciones 1 a 8, de una combinación pesticida de la reivindicación 9 o de una composición como se define en la reivindicación 10 para uno de los siguientes propósitos:
    -combatir o controlar plagas de invertebrados del grupo de insectos, arácnidos o nematodos;
    -proteger plantas en crecimiento del ataque o infestación por plagas de invertebrados; o
    15 14. Un compuesto como se define en cualquiera de las reivindicaciones 1 a 9 o un estereoisómero, sal aceptable desde el punto de vista veterinario, tautómero o N-óxido del mismo para uso como un medicamento.
  7. 15. Un compuesto como se define en cualquiera de las reivindicaciones 1 a 9, o una combinación de la reivindicación 10 para su uso en el tratamiento, control, prevención o protección de animales contra la infestación o infección por parásitos.
    68
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