AR048574A1 - Compuestos azaciclo n-sustituidos y n-oxidos, composiciones y metodos para controlar insectos que los comprenden - Google Patents

Compuestos azaciclo n-sustituidos y n-oxidos, composiciones y metodos para controlar insectos que los comprenden

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AR048574A1
AR048574A1 ARP040103670A ARP040103670A AR048574A1 AR 048574 A1 AR048574 A1 AR 048574A1 AR P040103670 A ARP040103670 A AR P040103670A AR P040103670 A ARP040103670 A AR P040103670A AR 048574 A1 AR048574 A1 AR 048574A1
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Argentina
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optionally substituted
alkylsulfonyloxy
alkyl
haloalkyl
alkoxycarbonyl
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ARP040103670A
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Fmc Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
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    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • 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
    • A01N47/02—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
    • 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
    • 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Compuestos azaciclo N-sustituidos y N-oxidos de la formula (1) donde: m, q, r, t y u están independientemente seleccionados del 0 o 1; y p es 0, 1, 2 o 3; X está seleccionado de halogeno, hidroxilo, hidroxialquilo, alquilo, alcoxi, haloalquilo, haloalcoxi, tio, alquiltio, acetoxialquilo, azidoalquilo, aminoalquilo, acetilaminoalquilo, alquilsulfonilo, alquilsulfoxi, pentahalotio, ciano, nitro, acetiloxi, alquilsulfoniloxi, alquilcarbonilo, alcoxicarbonilo, arilo, o ariloxi; Y está seleccionado de H, halogeno, alquilo haloalquilo, hidroxilo, hidroxialquilo, alcoxi, haloalcoxi, tio, alquiltio, pentahalotio, ciano, nitro, alquilsulfonilo, alquilsulfoxi, alquilsulfoniloxi, alquilcarbonilo, alcoxicarbonilo, arilo, o ariloxi; o X e Y tomados juntos con -OCR12R13O-, forman un anillo 1,3 dioxolano; donde R12 y R13 están independientemente seleccionados de H, halogeno, alquilo, haloalquilo, hidroxialquilo, alcoxi, haloalcoxi, alquiltio, ciano, nitro, alquilsulfoniloxi, alquilcarbonilo, alcoxicarbonilo, arilo, o ariloxi; o R12 y R13 tomados juntos con (=O), forman un anillo 1,3-dioxol-2-ona; R1, R2, R3, R4, y R5 están independientemente seleccionados de H, halogeno, alquilo, haloalquilo, hidroxilo, hidroxialquilo, alcoxi, haloalcoxi, tio, alquiltio, haloalquiltio, pentahalotio, ciano, nitro, alquilsulfonilo, haloalquilsulfonilo, alquilsulfinilo, haloalquil sulfinilo, alquilsulfoniloxi, haloalquilsulfoniloxi, alquilcarbonilo, alcoxicarbonilo, dialcoxialquilcarbonilo, alcoxicarbonilamino, alquilaminoxialquilo, alcoxi iminoalquilo, alqueniloxiiminoalquilo, arilo, ariloxi, dioxanilo, dioxolanilo o cualquiera de R1 y R2, o R2 y R3, o R3 y R4, o R4 y R5 tomados juntos con -OC(R19)2O-, OC(R19)2(R19)2O-, -OC(R19)2(R19)2-, -OC(R19)=N-, o -SC(R19)=N-, forman un anillo benzo fusionado, donde R19 es H, halogeno, alquilo o haloalquilo; y donde al menos uno de R1, R2, R3, R4, y R5 es otro que H; R7, R8, R9, R10, y R11 están independientemente seleccionadas de H, halogeno, alquilo, hidroxi, hidroxialquilo, hidroxialcoxi, alcoxi, alcoxialquilo, alcoxiiminoalquilo, haloalcoxiiminoalquilo, cianoalcoxiiminoalquilo, cianoimino tioalquilamino, alqueniloxiiminoalquilo, alquiniloxiiminoalquilo, cicloalcoxi, cicloalquilalcoxi, fenoxi, alcoxicarbonilfenoxi, alcoxialcoxi, alcoxialcoxialcoxi, alquiltio, alquilsulfonilo, alquilaminosulfonilo, dialquilaminosulfonilo, cicloalquilaminosulfonilo, alqueniloxi, alquiniloxi, haloalqueniloxi, alquilsulfoniloxi, opcionalmente sustituido ariloalcoxi, ciano, nitro, amino, alquilamino, alquil carbonilamino, alcoxicarbonilamino, cicloalquilalcoxi-carbonilamino, alqueniloxi-carbonilamino, alquiniloxi-carbonilamino, haloalquil- carbonilamino, alcoxi-alcoxicarbonil amino, alcoxicarbonilamino, alcoxicarboniloxi, alquenilamino carboniloxi, alquinilaminocarboniloxi, (alquil)(alcoxi carbonil)amino, alquilsulfonil amino, opcionalmente sustituido (heteroaril)(alcoxi carbonil) amino, opcionalmente sustituido arilocarbonil amino, alcoxicarbonilo, alquilaminocarboniloxi, alquil aminocarbonilamino, dialquilaminocarbonilamino, alquilamino(tiocarbonil)amino, dialquilfosforoureido, acetoxialcoxi, sulfoniloxialcoxi, dialcoxialcoxi, trialcoxialcoxi, dialcoxialquiloacetal, trialcoximetiloortoester, acetal cíclico, opcionalmente sustituido acetal cíclico, opcionalmente sustituido tienilo, opcionalmente sustituido 1,3-tiazoliloalcoxi, opcionalmente sustituido arilo, opcionalmente sustituido ariloxi, opcionalmente sustituido ariloxialquilo, opcionalmente sustituido arilaminocarboniloxi, opcionalmente sustituido ariloalcoxicarbonilamino, opcionalmente sustituido heteroarilo, opcionalmente sustituido heteroariloxi, opcionalmente sustituido pirrolilo, opcionalmente sustituido pirazolilo, opcionalmente sustituido piraziniloxi, opcionalmente sustituido cicloalquilcarbonilamino, opcionalmente sustituido 1,3-oxazolinilo, opcionalmente sustituido 1,3- oxazoliniloxi, opcionalmente sustituido 1,3-oxazolinilamino, opcionalmente sustituido 1,2,4-triazolilo, opcionalmente sustituido 1,2,3-tiadiazolilo, opcionalmente sustituido 1,2,5-tiadiazolilo, opcionalmente sustituido 1,2,5-tiadiazoliloxi, opcionalmente sustituido 2H-tetrazolilo, opcionalmente sustituido piridilo, opcionalmente sustituido piridiloxi, opcionalmente sustituido piridilamino, opcionalmente sustituido pirimidinilo, opcionalmente sustituido pirimidiniloxi, opcionalmente sustituido 3,4,5,6-tetrahidropirimidiniloxi, opcionalmente sustituido piridaziniloxi, u opcionalmente sustituido 1,2,3,4-tetrahidronaftalenilo, donde el sustituyente opcional está seleccionado de uno o más halogeno, alquilo, haloalquilo, alcoxi, ciano, nitro, amino, alquilcarbonilo, alcoxicarbonilo, alcoxiiminoalquilo, dialquilacetal, alquiltiol, alquilsufoxido, o alcoxicarbonilamino; y, donde al menos uno de R7, R8, R9, R10, y R11 es otro que H; R es alquilo, cicloalquilo, alquenilo, alcoxicarbonilo, opcionalmente sustituido pirid-2-ilo donde el sustituyente opcional está seleccionado de H, halogeno, haloalcoxi o haloalquilo, o el fenilo sustituido tiene la estructura de formula (2) donde R14, R15, R16, R17, y R18 están independientemente seleccionados de H, halogeno, alquilo, haloalquilo, hidroxilo, hidroxialquilo, alcoxi, haloalcoxi, tio, alquiltio, haloalquiltio, pentahalotio, ciano, nitro, alquilsulfonilo, haloalquilsulfonilo, alquilsulfinilo, haloalquilsulfinilo, alquilsulfoniloxi, haloalquilsulfoniloxi, alquilcarbonilo, alcoxicarbonilo, dialcoxialquilcarbonilo, alcoxicarbonilamino, alquilaminoxialquilo, alcoxiiminoalquilo, alqueniloxiiminoalquilo, arilo, ariloxi, dioxanilo, dioxolanilo o cualquiera de R14 y R15, o R15 y R16, o R16 y R17, o R17 y R18 tomadas juntas con -OC(R19)2O-, OC(R19)2(R19)2O-, -OC(R19)2(R19)2-, -OC(R19)=N-, o SC(R19)=N-, forman un anillo benzo fusionado, donde R19 es H, halogeno, alquilo o haloalquilo; y donde al menos uno de R14, R15, R16, R17, y R18 es otro que H; A está seleccionada de -CH2-, -CH2CH2-, -CH2CH2CH2-, OCH2CH2-, OCH2CH2CH2-, -OCH2CH2CH2CH2-, -OCH2CH(OH)CH2-, NHCH2CH2-, N(CH3)CH2CH2-, N[C(=O)CH3]CH2CH2-, o -N[C(=O)OCH3]CH2CH2-; B está seleccionada del -O-, -S-, -CH2O-, -OCH2-, -OC(=O)NH-, -OC(=O)O-, o -NHSO2-; cuando p es 1, 2 o 3; D es -CH2-; R6 está seleccionada de alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, dialquilaminoalquilo, alquilaminocarboniloxialquilo, alquiltioalquilo, alquilsulfonilalquilo, alquilcarboniloxialquilo, alcoxicarbonil alquilo, carboxialquilo, ariloalquilo, arilocarbonilo, sulfonato, o sulfonatoalquilo, y pueden llevar una carga negativa resultando en una sal más interna y el ion separado es cloruro, bromuro, yoduro, o un alquilo o fenil sulfato o sulfonato; y las sales agrícolamente aceptables de los mismos. Composiciones y métodos para controlar insectos que los comprenden
ARP040103670A 2003-10-10 2004-10-08 Compuestos azaciclo n-sustituidos y n-oxidos, composiciones y metodos para controlar insectos que los comprenden AR048574A1 (es)

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US60953304P 2004-09-13 2004-09-13

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MXPA06003860A (es) 2006-07-03
US8119563B2 (en) 2012-02-21
EP1673083A2 (en) 2006-06-28
WO2005036961A2 (en) 2005-04-28
JP2007508306A (ja) 2007-04-05
IL174421A0 (en) 2006-08-01
KR20060119996A (ko) 2006-11-24
US20090215821A1 (en) 2009-08-27
AU2004281683A1 (en) 2005-04-28

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