ES2558166T3 - Compuestos de N-tio-antranilamida y su uso como pesticidas - Google Patents
Compuestos de N-tio-antranilamida y su uso como pesticidas Download PDFInfo
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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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- 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
20
25
- 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
56
Claims (7)
-
imagen1 imagen2 imagen3 - 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
-
- 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.
-
- 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.
-
- 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.
-
- 11.
- Una composición agrícola o veterinaria que comprende al menos un compuesto como se define en una
675 cualquiera de las reivindicaciones 1 a 9 o la combinación plaguicida de la reivindicación 10 y al menos un vehículo líquido y/o sólido. - 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; o15 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.
- 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161522721P | 2011-08-12 | 2011-08-12 | |
US201161522721P | 2011-08-12 | ||
PCT/EP2012/065650 WO2013024009A1 (en) | 2011-08-12 | 2012-08-10 | N-thio-anthranilamide compounds and their use as pesticides |
Publications (1)
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-
2012
- 2012-08-10 EP EP12750733.3A patent/EP2742037B1/en not_active Not-in-force
- 2012-08-10 US US14/235,528 patent/US9044016B2/en not_active Expired - Fee Related
- 2012-08-10 AU AU2012297004A patent/AU2012297004A1/en not_active Abandoned
- 2012-08-10 BR BR112014003217A patent/BR112014003217A2/pt active Search and Examination
- 2012-08-10 EA EA201400212A patent/EA201400212A1/ru unknown
- 2012-08-10 CA CA2842858A patent/CA2842858A1/en not_active Abandoned
- 2012-08-10 KR KR1020147006253A patent/KR20140051402A/ko not_active Application Discontinuation
- 2012-08-10 AR ARP120102940A patent/AR087516A1/es not_active Application Discontinuation
- 2012-08-10 ES ES12750733.3T patent/ES2558166T3/es active Active
- 2012-08-10 IN IN979CHN2014 patent/IN2014CN00979A/en unknown
- 2012-08-10 WO PCT/EP2012/065650 patent/WO2013024009A1/en active Application Filing
- 2012-08-10 JP JP2014524394A patent/JP2014522875A/ja active Pending
- 2012-08-10 MX MX2014001609A patent/MX2014001609A/es not_active Application Discontinuation
- 2012-08-10 CN CN201280048108.7A patent/CN103857666B/zh not_active Expired - Fee Related
-
2014
- 2014-01-22 IL IL230596A patent/IL230596A0/en unknown
- 2014-01-28 CR CR20140045A patent/CR20140045A/es unknown
- 2014-02-11 CO CO14028775A patent/CO6880072A2/es not_active Application Discontinuation
- 2014-03-10 ZA ZA2014/01723A patent/ZA201401723B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ZA201401723B (en) | 2015-08-26 |
CO6880072A2 (es) | 2014-02-28 |
US20140155264A1 (en) | 2014-06-05 |
BR112014003217A2 (pt) | 2017-04-25 |
MX2014001609A (es) | 2014-05-01 |
IL230596A0 (en) | 2014-03-31 |
CN103857666B (zh) | 2016-12-14 |
EP2742037A1 (en) | 2014-06-18 |
EP2742037B1 (en) | 2015-10-14 |
AU2012297004A1 (en) | 2014-03-06 |
US9044016B2 (en) | 2015-06-02 |
EA201400212A1 (ru) | 2014-07-30 |
IN2014CN00979A (es) | 2015-04-10 |
CR20140045A (es) | 2014-03-05 |
AR087516A1 (es) | 2014-03-26 |
CN103857666A (zh) | 2014-06-11 |
JP2014522875A (ja) | 2014-09-08 |
CA2842858A1 (en) | 2013-02-21 |
KR20140051402A (ko) | 2014-04-30 |
WO2013024009A1 (en) | 2013-02-21 |
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