AR087515A1 - Compuestos de n-tio-antranilamida y sus usos como plaguicidas - Google Patents

Compuestos de n-tio-antranilamida y sus usos como plaguicidas

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AR087515A1
AR087515A1 ARP120102938A ARP120102938A AR087515A1 AR 087515 A1 AR087515 A1 AR 087515A1 AR P120102938 A ARP120102938 A AR P120102938A AR P120102938 A ARP120102938 A AR P120102938A AR 087515 A1 AR087515 A1 AR 087515A1
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Argentina
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radicals
substituted
partially
nr9a
totally
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Basf Se
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
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    • C07D239/28—Heterocyclic 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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    • 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
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Abstract

Compuestos de N-tio-antranilamida y los estereoisómeros, las sales, los tautómeros y los N-óxidos de estos, y las composiciones que los comprenden. También, uso de los compuestos de N-tio-antranilamida o de las composiciones que comprenden tales compuestos para combatir las plagas de invertebrados. Además, métodos para aplicar dichos compuestos.Reivindicación 1: Un compuesto de la fórmula general (1) en donde A1, A2, A3 y A4 son N o CH, siempre que, como máximo, dos de A1, A2, A3 y A4 sean N; B1 es N o CH; cada R1 se selecciona independientemente del grupo que consiste en halógeno; ciano; azido; nitro; -SCN; SF5; alquilo C1-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; cicloalquilo C3-8 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; alquenilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; alquinilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; -Si(R14)2R13; -OR8; -OS(O)nR8; -SR8; -S(O)mR8; -S(O)nN(R9a)R9b; -N(R9a)R9b; -N(R9a)C(=O)R7; -C(=O)R7; -C(=O)OR8; -C(=NR9a)R7; -C(=O)N(R9a)R9b; -C(=S)N(R9a)R9b; fenilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10; y un anillo heterocíclico saturado, parcial o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir con uno o más radicales R10; o dos radicales R1 unidos en átomos de carbono adyacentes pueden ser, en forma conjunta, un grupo seleccionado de -CH2CH2CH2CH2-, -CH=CH-CH=CH-, -N=CH-CH=CH-, -CH=N-CH=CH-, -N=CH-N=CH-, -OCH2CH2CH2-, -OCH=CHCH2-, -CH2OCH2CH2-, -OCH2CH2O-, -OCH2OCH2-, -CH2CH2CH2-, -CH=CHCH2-, -CH2CH2O-, -CH=CHO-, -CH2OCH2-, -CH2C(=O)O-, -C(=O)OCH2-, -O(CH2)O-, -SCH2CH2CH2-, -SCH=CHCH2-, -CH2SCH2CH2-, -SCH2CH2S-, -SCH2SCH2-, -CH2CH2S-, -CH=CHS-, -CH2SCH2-, -CH2C(=S)S-, -C(=S)SCH2-, -S(CH2)S-, -CH2CH2NR18-, -CH2CH=N-, -CH=CH-NR18-, -OCH=N- y -SCH=N-, para así formar, junto con los átomos de carbono a los que están unidos, un anillo de 5 ó 6 miembros, en donde los átomos de hidrógeno de los grupos anteriores se pueden reemplazar por uno o más sustituyentes seleccionados de halógeno, metilo, halometilo, hidroxilo, metoxi y halometoxi, o uno o más grupos CH2 de los grupos anteriores se pueden reemplazar por un grupo C=O; R2 se selecciona del grupo que consiste en hidrógeno; ciano; alquilo C1-10 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; cicloalquilo C3-8 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; alquenilo C2-10 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; alquinilo C2-10 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7; -N(R9a)R9b; -Si(R14)2R13; -OR8; -SR8; -S(O)mR8; -S(O)nN(R9a)R9; -C(=O)R7; -C(=O)OR8; -C(=O)N(R9a)R9b; -C(=S)R7; -C(=S)OR8; -C(=S)N(R9a)R9b; -C(=NR9a)R7; fenilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10; y un anillo heterocíclico saturado, parcial o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir con uno o más radicales R10; cada R3 se selecciona independientemente del grupo que consiste en halógeno, ciano, azido, nitro, -SCN, SF5, alquilo C1-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, cicloalquilo C3-8 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, alquenilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, alquinilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, -Si(R14)2R13, -OR8, -OS(O)nR8, -SR8, -S(O)mR8, -S(O)nN(R9a)R9b, -N(R9a)R9b, -N(R9a)C(=O)R7, -C(=O)R7, -C(=O)OR8, -C(=S)R7, -C(=S)OR8, -C(=NR9a)R7, -C(=O)N(R9a)R9b, -C(=S)N(R9a)R9b, fenilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10, y un anillo heterocíclico saturado, parcial o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir con uno o más radicales R10; cada R4 se selecciona independientemente del grupo definido para R3; R5, R6 se seleccionan, independientemente entre sí, del grupo que consiste en alquilo C1-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, alquenilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, alquinilo C2-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R7, R7, -C(=G)R7, -C(=NOR8)R7, C[=NN(R9a)R9b]R7, -C(=G)OR8, -C(=G)N(R9a)R9b, -OC(=G)R7, -OC(=G)OR8, -NR9aC(=G)R7, -N[C(=G)R7]2, -NR9aC(=G)OR8, -C(=G)N(R9a)-N(R9b)2, -C(=G)NR9a-NR9b[C(=G)R7], -NR9a-C(=G)N(R9b)2, -NR9aNR9bC(=G)R7, -NR9a-N[C(=G)R7]2, -N[(C=G)R7]-N(R9a)2 -NR9a-NR9b[(C=G)GR8], -NR9a[(C=G)N(R9b)2], -NR9a[C=NR9b]R7, -NR9a(C=NR9b)N(R9b)2, -O-N(R9a)2, -O-NR9a(C=G)R7, -SO2NR9aR9b, -NR9aSO2R8, -SO2OR8, -OSO2R8, -OR8, -NR9aR9b, -SR8, -Si(R14)2R13, -PR9aR9b, -P(=G)R9a, -SOR8, -SO2R8, -PG2(R9a)2 y -PG3R72; en donde G es O, S o NR9a; o R5 y R6 junto con el átomo de azufre al que están unidos, forman un anillo saturado, parcial o totalmente insaturado de 3, 4, 5, 6, 7 u 8 miembros que contiene, de manera opcional, 1, 2, 3 ó 4 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2 como miembros del anillo, en donde el anillo puede estar fusionado con uno o dos anillos carbocíclicos o heterocíclicos saturados, parcial o totalmente insaturados de 5 ó 6 miembros que pueden contener 1, 2, 3 ó 4 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde todos los anillos anteriores son no sustituidos o sustituidos mediante cualquier combinación de 1, 2, 3, 4, 5 ó 6 radicales R10; cada R7 se selecciona independientemente del grupo que consiste en ciano, azido, nitro, -SCN, SF5, cicloalquilo C3-8, halocicloalquilo C3-8, -Si(R14)2R13, -OR8, -OSO2R8, -SR8, -S(O)mR8, -S(O)nN(R9a)R9b, -N(R9a)R9b, -C(=O)N(R9a)R9b, -C(=S)N(R9a)R9b, -C(=O)OR8, -C(=O)R19, fenilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10, y un anillo heterocíclico saturado, parcial o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir con uno o más radicales R10; y, en caso de que R7 se una a un grupo cicloalquilo o a un anillo heterocíclico, R7 también se puede seleccionar del grupo que consiste en alquilo C1-6, haloalquilo C1-6, alcoxi C1-6-alquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6 y bencilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10; y en grupos -C(=O)R7, -C(=S)R7, -C(=NR9a)R7, -N(R9a)C(=O)R7, -C(=G)R7, -C(=NOR8)R7, -C[=NN(R9a)R9b]R7, -OC(=G)R7, -NR9aC(=G)R7, -N[C(=G)R7]2, -C(=G)NR9a-NR9b[C(=G)R7], -NR9a-NR9bC(=G)R7, -NR9a-N[C(=G)R7]2, -N[(C=G)R7]-N(R9a)2, -NR9a[C=NR9b]R7, -O-NR9a(C=G)R7 y -PG3R72, R7 también se puede seleccionar de hidrógeno, halógeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6-alquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6 y bencilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10; o dos radicales R7 unidos de manera geminal forman junto un grupo seleccionado de =CR11R12, =S(O)mR8, =S(O)mN(R9a)R9b, =NR9a, =NOR8 y =NNR9aR9b; o dos radicales R7, junto con los átomos de carbono a los que están unidos, forman un anillo carbocíclico o heterocíclico de 3, 4, 5, 6, 7 u 8 miembros, saturado o parcialmente insaturado que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo; cada R8 se selecciona independientemente del grupo que consiste en hidrógeno, ciano, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-4, halocicloalquilo C3-8, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, -Si(R14)2R13, -SR20, -S(O)mR20, -S(O)nN(R9a)R9b, -N(R9a)R9b, -N=CR15R16, -C(=O)R19, -C(=O)N(R9a)R9b, -C(=S)N(R9a)R9b, -C(=O)OR20, fenilo que se puede sustituir con 1, 2, 3, 4 ó 5 radicales R10, y un anillo heterocíclico saturado, parcial o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos de heteroátomos seleccionados de N, O, S, NO, SO y SO2, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir con uno o más radicales R10; siempre que R8 no sea alcoxi C1-6 ni haloalcoxi C1-6 si se une en un átomo de oxígeno; R9a, R9b se seleccionan, independientemente entre sí e independientemente en cada caso, del grupo que consiste en hidrógeno, ciano, alquilo C1-6 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R19, alcoxi C1-6, haloalcoxi C1-6, alquiltio C1-6, haloalquiltio C1-6, en donde la porción alquilo en los cuatro últimos radicales mencionados se puede sustituir con uno o más radicales R19, cicloalquilo C3-8 que puede ser parcial o totalmente halogenado y/o se puede sustituir con uno o más radicales R19, cicloalquil C3-8-alquilo C1-4 que puede ser parcial o totalmente halogenado y/o se puede sustituir con
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US20140243195A1 (en) 2014-08-28
BR112014003221A2 (pt) 2017-04-18

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