ES2553417T3 - Nuevos herbicidas - Google Patents

Nuevos herbicidas Download PDF

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Publication number
ES2553417T3
ES2553417T3 ES09765114.5T ES09765114T ES2553417T3 ES 2553417 T3 ES2553417 T3 ES 2553417T3 ES 09765114 T ES09765114 T ES 09765114T ES 2553417 T3 ES2553417 T3 ES 2553417T3
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formula
compound
alkyl
pyridyl
furanyl
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ES09765114.5T
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John Benjamin Taylor
Jeffrey Steven Wailes
Stephane André Marie JEANMART
Mangala Govenkar
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Syngenta Participations AG
Syngenta Ltd
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Syngenta Participations AG
Syngenta Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Un compuesto de fórmula I**Fórmula** en la que G es hidrógeno o un metal agrícolamente aceptable, sulfonio, amonio o grupo protector, R1 es metilo, etilo, n-propilo, isopropilo, ciclopropilo, halometilo, haloetilo, vinilo, etinilo, halógeno, alcoxi de C1-C2 o haloalcoxi de C1-C2, R2 y R3 son, cada uno independientemente entre sí, hidrógeno, metilo, etilo, n-propilo, isopropilo, ciclopropilo, halometilo, haloetilo, vinilo, propenilo, etinilo, propinilo, halógeno, alcoxi de C1-C2, haloalcoxi de C1-C2, arilo opcionalmente sustituido o heteroarilo opcionalmente sustituido, y en la que, en R2 y R3, cuando están presentes, los susituyentes opcionales en el arilo se seleccionan, independientemente, de: halógeno, nitro, ciano, rodano, isotiocianato, alquilo de C1-C6, haloalquilo de C1-C6, alcoxi de C1-C6-alquilo (C1-C6), alquenilo de C2-C6, haloalquenilo de C2-C6, alquinilo de C2-C6, cicloalquilo de C3-C7 (él mismo opcionalmente sustituido con alquilo de C1-C6 o halógeno), cicloalquenilo de C5-7 (él mismo opcionalmente sustituido con alquilo de C1-C6 o halógeno), hidroxi, alcoxi de C1-C10, alcoxi de C1-C10-alcoxi (C1-C10), tri-alquil (C1- C4)silil-alcoxi (C1-C6), alcoxi de C1-C6-carbonil-alcoxi (C1-C10), haloalcoxi de C1-C10, aril-alcoxi (C1-C4) (en el que el grupo arilo está opcionalmente sustituido con halógeno o alquilo de C1-C6), cicloalquil C3-C7-oxi (en el que el grupo cicloalquilo está opcionalmente sustituido con alquilo de C1-C6 o halógeno), alquenil C3-C10-oxi, alquinil C3-C10-oxi, mercapto, alquil C1-C10-tio, haloalquil C1-C10-tio, aril-alquil (C1-C4)tio, cicloalquil C3-C7-tio (en el que el grupo cicloalquilo está opcionalmente sustituido con alquilo de C1-C6 o halógeno), trialquil (C1-C4)-silil-alquil (C1-C6)tio, ariltio, alquil C1-C6-sulfonilo, haloalquil C1-C6-sulfonilo, alquil C1-C6-sulfinilo, haloalquil C1-C6-sulfinilo, arilsulfonilo, trialquil (C1-C4)sililo, arildi-alquil (C1-C4)sililo, alquil C1-C4-diarilsililo, triarilsililo, alquil C1-C10-carbonilo, HO2C, alcoxi de C1-C10-carbonilo, aminocarbonilo, alquil C1-C6-aminocarbonilo, di(alquil C1-C6)-aminocarbonilo, N-(alquil C1-C3)-N- (alcoxi C1-C3)-aminocarbonilo, alquil C1-C6-carboniloxi, arilcarboniloxi, di-alquil (C1-C6)-aminocarboniloxi, arilo (él mismo opcionalmente sustituido con alquilo de C1-C6 o halógeno), heterociclilo (él mismo opcionalmente sustituido con alquilo de C1-C6 o halógeno), ariloxi (en el que el grupo arilo está opcionalmente sustituido con alquilo de C1-C6 o halógeno), heterocicliloxi (en el que el grupo heterociclilo está opcionalmente sustituido con alquilo de C1-C6 o halógeno), amino, alquil C1-C6-amino, di-alquil (C1-C6)-amino, alquil C1-C6-carbonilamino, N-alquil (C1-C6)carbonil-Nalquil (C1-C6)-amino, o arilcarbonilo (en el que el grupo arilo está él mismo opcionalmente sustituido con halógeno o alquilo de C1-C6); o dos posiciones adyacentes en el sistema arílico se ciclan para formar un anillo heterocíclico o carbocíclico de 5, 6 o 7 miembros, él mismo opcionalmente sustituido con halógeno o alquilo de C1-C6; y en la que, en R2 y R3, cuando están presentes, el heteroarilo está opcionalmente sustituido con alquilo de C1-C4, haloalquilo de C1-C3, alcoxi de C1-C3, haloalcoxi de C1-C3, ciano, nitro, halógeno, alquil C1-C3-tio, alquil C1-C3- sulfinilo o alquil C1-C3-sulfonilo; R4 es metilo, etilo, n-propilo, isopropilo, ciclopropilo, halometilo, haloetilo, vinilo, propenilo, etinilo, propinilo, halógeno, alcoxi de C1-C2 o haloalcoxi de C1-C2, y R5, R6, R7, R8 y R9 son independientemente hidrógeno, halógeno, alquilo de C1-C6, haloalquilo de C1-C6, alcoxi de C1-C6, haloalcoxi de C1-C6, alquenilo de C2-C6, haloalquenilo de C2-C6, alquinilo de C2-C6, alquenil C3-C6-oxi, haloalquenil C3-C6-oxi, alquinil C3-C6-oxi, cicloalquilo de C3-C6, alquil C1-C6-tio, alquil C1-C6-sulfinilo, alquil C1-C6- sulfonilo, alcoxi de C1-C6-sulfonilo, haloalcoxi de C1-C6-sulfonilo, ciano, nitro, fenilo, fenilo sustituido con alquilo de C1-C4, haloalquilo de C1-C3, alcoxi de C1-C3, haloalcoxi de C1-C3, ciano, nitro, halógeno, alquil C1-C3-tio, alquil C1-C3- sulfinilo o alquil C1-C3-sulfonilo, o heteroarilo o heteroarilo sustituido con alquilo de C1-C4, haloalquilo de C1-C3, alcoxi de C1-C3, haloalcoxi de C1-C3, ciano, nitro, halógeno, alquil C1-C3-tio, alquil C1-C3-sulfinilo o alquil C1-C3-sulfonilo, o R6 y R7 o R8 y R9, junto con los átomos de carbono a los que están unidos, forman un anillo carbocíclico opcionalmente sustituido o un heterociclilo opcionalmente sustituido con alquilo de C1-C6 o haloalquilo de C1-C6; y en el que "anillo carbocíclico" significa un grupo cicloalquilo o cicloalquenilo; y en el que, cuando están presentes, los sustituyentes opcionales en ciclolalquilo o cicloalquenilo con alquilo de C1-C3; o

Description

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arilo está sustituido con alquilo de C1-C6 o halógeno), aril-N-alquil (C1-C6)-amino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno), arilamino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno), heteroarilamino (en el que el grupo heteroarilo está sustituido con alquilo de C1-C6 o halógeno), heterociclilamino (en el que el grupo heterociclilo está sustituido con alquilo de C1-C6 o halógeno), aminocarbonilamino, alquil C1-C6-aminocarbonilamino, dialquil (C1-C6)-aminocarbonilamino, arilaminocarbonilamino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno), aril-N-alquil (C1-C6)-aminocarbonilamino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno), alquil C1-C6-aminocarbonil-N-alquil (C1-C6)amino, dialquil (C1-C6)-aminocarbonil-N-alquil (C1-C6)-amino, arilaminocarbonil-N-alquil (C1-C6)-amino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno) y aril-N-alquil (C1-C6)-aminocarbonil-N-alquil (C1-C6)amino (en el que el grupo arilo está sustituido con alquilo de C1-C6 o halógeno).
Para grupos heterociclilo sustituidos, se prefiere que uno o más sustituyentes se seleccionen independientemente de halógeno, alquilo de C1-C6, haloalquilo de C1-C6, alcoxi de C1-C6, haloalcoxi de C1-C6, alquil C1-C6-tio, alquil C1-C6sulfinilo, alquil C1-C6-sulfonilo, nitro y ciano. Se entenderá que los sustituyentes dialquilamino incluyen aquellos en los que los grupos dialquilo junto con el átomo de N al que están unidos forman un anillo heterocíclico de cinco, seis
o siete miembros que puede contener uno o dos heteroátomos adicionales seleccionados de O, N o S y que está opcionalmente sustituido con uno o dos grupos alquilo de C1-C6 seleccionados independientemente. Cuando los anillos heterocíclicos se forman uniendo dos grupos sobre un átomo de N, los anillos resultantes son adecuadamente pirrolidina, piperidina, tiomorfolina y morfolina, cada uno de los cuales puede estar sustituido con uno o dos grupos alquilo de C1-C6 seleccionados independientemente.
La invención también se refiere a las sales agrícolamente aceptables que los compuestos de fórmula I son capaces de formar con bases de metales de transición, de metales alcalinos y de metales alcalino-térreos, aminas, bases de amonio cuaternario o bases de sulfonio terciario.
Entre los formadores de sales de metales de transición, de metales alcalinos y de metales alcalino-térreos, se debería hacer mención especial a los hidróxidos de cobre, hierro, litio, sodio, potasio, magnesio y calcio, pero preferiblemente los hidróxidos, bicarbonatos y carbonatos de sodio y potasio.
Ejemplos de aminas adecuadas para la formación de sales de amonio incluyen amoniaco así como alquil C1-C18aminas, hidroxialquil C1-C4-aminas y alcoxi C2-C4-alquilaminas primarias, secuendarias y terciarias, por ejemplo metilamina, etilamina, n-propilamina, isopropilamina, los cuatro isómeros de butilamina, n-amilamina, isoamilamina, hexilamina, heptilamina, octilamina, nonilamina, decilamina, pentadecilamina, hexadecilamina, heptadecilamina, octadecilamina, metiletilamina, metilisopropilamina, metilhexilamina, metilnonilamina, metilpentadecilamina, metiloctadecilamina, etilbutilamina, etilheptilamina, etiloctilamina, hexilheptilamina, hexiloctilamina, dimetilamina, dietilamina, di-n-propilamina, di-isopropilamina, di-n-butilamina, di-n-amilamina, di-isoamilamina, dihexilamina, diheptilamina, dioctilamina, etanolamina, n-propanolamina, isopropanolamina, N,N-dietanolamina, Netilpropanolamina, N-butiletanolamina, alilamina, n-but-2-enilamina, n-pent-2-enilamina, 2,3-dimetilbut-2-enilamina, dibut-2-enilamina, n-hex-2-enilamina, propilendiamina, trimetilamina, trietilamina, tri-n-propilamina, tri-isopropilamina, tri-n-butilamina, tri-isobutilamina, tri-sec-butilamina, tri-n-amilamina, metoxietilamina y etoxietilamina; aminas heterocíclicas, por ejemplo piridina, quinolina, isoquinolina, morfolina, piperidina, pirrolidina, indolina, quinuclidina y azepina; arilaminas primarias, por ejemplo anilinas, metoxianilinas, etoxianilinas, o-, m-y p-toluidinas, fenilendiaminas, bencidinas, naftilaminas y o-, m-y p-cloroanilinas; pero especialmente trietilamina, isopropilamina y diisopropilamina.
Las base de amonio cuaternario preferidas adecuadas para la formación de sales corresponde, por ejemplo, a la fórmula [N(Ra Rb Rc Rd)]OH en la que Ra, Rb, Rc y Rd son, cada uno independientemente entre sí, hidrógeno, alquilo de C1-C4. Otras bases de tetraalquilamonio adecuadas con otros aniones se pueden obtener, por ejemplo, mediante reacciones de intercambio aniónico.
Las bases preferidas de sulfonio terciario adecuadas para la formación de sal corresponde, por ejemplo, a la fórmula [SReRfRg]OH, en la que Re, Rf y Rg son cada uno, independientemente entre sí, alquilo de C1-C4. Se prefiere de manera especial hidróxido de trimetilsulfonio. Las bases de sulfonio adecuadas se pueden obtener de la reacción de tioéteres, en particular de sulfuros de alquilo, con haluros de alquilo, seguido de la conversión en una base adecuada, por ejemplo un hidróxido, mediante reacciones de intercambio aniónico.
Se debería entender que en aquellos compuestos de fórmula I en la que G es un metal, amonio o sulfonio como se menciona anteriormente y como tal representa un catión, la carga negativa correspondiente está muy deslocalizada a lo largo de la unidad O-C=C-C=O.
Los compuestos de fórmula I según la invención también incluyen los hidratos que se pueden formar durante la formación de sales.
Los grupos protectores G se seleccionan para permitir su eliminación mediante uno o una combinación de procedimientos bioquímicos, químicos o físicos para dar compuestos de fórmula I en la que G es H antes, durante o después de la aplicación al área o plantas tratadas. Los ejemplos de estos procedimientos incluyen escisión enzimática, hidrólisis química, y fotolisis. Los compuestos que poseen tales grupos G pueden ofrecer ciertas
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En particular, el grupo protector G es un grupo -C(Xa)-Ra o -C(Xb)-Xc-Rb, y los significados de Xa, Ra, Xb, Xc y Rb son como se definen anteriormente.
Se prefiere que G sea hidrógeno, un metal alcalino o un metal alcalino-térreo, en el que se prefiere especialmente hidrógeno.
Dependiendo de la naturaleza de los sustituyentes, los compuestos de fórmula I pueden existir en diferentes formas isómeras. Cuando G es hidrógeno, por ejemplo, los compuestos de fórmula I pueden existir en diferentes formas tautómeras:
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Esta invención cubre todos estos isómeros y tautómeros, y sus mezclas en todas las proporciones. También, cuando los sustituyentes contienen dobles enlaces, pueden existir isómeros cis y trans. Estos isómeros están, también, dentro del alcance de los compuestos reivindicados de la fórmula I.
Para los fines de claridad, un compuesto de fórmula I, en la que G es H, se representa como un único tautómero, incluso si está presente en una forma tautómera diferente, o como una mezcla de formas tautómeras. Preferiblemente, en los compuestos de la fórmula I,
R1 es metilo, etilo, n-propilo, vinilo, etinilo, halógeno, alcoxi de C1-C2 o haloalcoxi de C1-C2, especialmente metilo, R2 es metilo, halógeno, alcoxi de C1-C2 o haloalcoxi de C1-C2, o fenilo opcionalmente sustituido, especialmente metilo,
R3 es hidrógeno, y R4 es metilo, etilo, n-propilo, vinilo, etinilo o metoxi, R5, R6, R7, R8 y R9 son independientemente hidrógeno, halógeno, alquilo de C1-C4, haloalquilo de C1-C4, alcoxi de
C1-C4, haloalcoxi de C1-C4, alquenilo de C2-C4, haloalquenilo de C2-C4, alquinilo de C2-C4,
R6 y R7 o R8 y R9, junto con los átomos de carbono a los que están unidos, forman un anillo carbocíclico opcionalmente sustituido o un heterociclilo opcionalmente sustituido, o R5 y R6 forman juntos un enlace, y HetAr es heteroarilo o heteroarilo sustituido una a tres veces con fluoro, cloro, bromo, metilo, metoxi, ciano o
trifluorometilo. Más preferiblemente, R1 es metilo o etilo, R2 es metilo o cloro, R3 es hidrógeno, R4 es metilo, etilo o metoxi, R5, R6, R7, R8 y R9 son
hidrógeno, o R5 y R6 forman juntos un enlace, y HetAr es un heteroarilo de 5 o 6 miembros, o es un heteroarilo de 5 o 6 miembros que está sustituido una a tres
veces con fluoro, cloro, bromo, metilo, metoxi, ciano o trifluorometilo.
Preferiblemente, los heteroátomos en estos restos HetAr se seleccionan de 1 o 2 átomos de nitrógeno, oxígeno o azufre. En particular, HetAr es tienilo, furilo, oxazolilo, isoxazolilo, benzofurilo, tiazolilo, oxazolilo, isotiazolilo, benzotienilo,
benzoisotienilo, benzotiazolilo, bencisotiazolilo, benzoxazolilo y bencisoxazolilo, en el que estos anillos están
opcionalmente sustituidos una o dos veces con fluoro, cloro, bromo, metilo, metoxi, ciano o trifluorometilo. En particular, HetAr es piridilo, pirimidinilo, piridazinilo, quinolinilo, isoquinolinilo, cinolinilo, ftalazinilo, quinazolinilo y quinoxalinilo, en el que estos anillos están opcionalmente sustituidos una o dos veces con fluoro, cloro, bromo, metilo, metoxi, ciano o trifluorometilo.
En otro grupo de compuestos preferidos de la fórmula I, R1 es metilo, etilo, n-propilo, ciclopropilo, halógeno o haloalcoxi de C1-C2, especialmente etilo, R2 es hidrógeno, R3 es fenilo o piridilo, en el que estos anillos están
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opcionalmente sustituidos una a tres veces con fluoro, cloro, bromo, metilo, metoxi, ciano o trifluorometilo, y R4 es hidrógeno.
Ciertos compuestos de fórmula (I) son alquenos, y como tales sufren reacciones adicionales típicas de alquenos para dar compuestos adicionales de fórmula (I) según procedimientos conocidos. El ejemplo de tal reacción incluye, pero no se restringe a, halogenación o hidrogenación.
Los compuestos de fórmula (I) en los que R5 y R6 forman un enlace y R7 es halógeno, preferiblemente cloruro o bromuro, pueden experimentar una reacción de acoplamiento cruzado con una pareja adecuada de acoplamiento bajo condiciones descritas en la bibliografía para las reacciones de Suzuki-Miyaura, Sonogashira y reacciones de acoplamiento cruzado relacionadas, para dar compuestos adicionales de fórmula (I) (véanse, por ejemplo, O’Brien,
C. J. y Organ, M. G. Angew. Chem. Int. Ed. (2007), 46, 2768-2813; Suzuki, A. Journal of Organometallic Chemistry (2002), 653, 83; Miyaura N. y Suzuki, A. Chem. Rev. (1995), 95, 2457-2483).
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en la que R5 y R6 forman un enlace
Los expertos en la técnica apreciarán que los compuestos de fórmula (I) pueden contener un resto aromático que posee uno o más sustituyentes capaces de ser transformados en sustituyentes alternativos en condiciones conocidas, y que estos compuestos pueden servir ellos mismos como intermedios en la preparación de compuestos adicionales de fórmula (I).
Por ejemplo, los compuestos de fórmula (I) en la que R1, R2, R3 o R4 es alquenilo o alquilo, se pueden reducir a compuestos de fórmula (I) en la que R1, R2, R3 o R4 es alquilo en condiciones conocidas, y los compuestos de fórmula (I) en la que R1, R2, R3 o R4 es halógeno, preferiblemente bromuro o yodo, pueden experimentar una reacción de acoplamiento cruzado con una pareja adecuada de acoplamiento en condiciones descritas en la bibliografía para reacciones de Suzuki-Miyaura, Sonogashira y reacciones de acoplamiento cruzado relacionadas, para dar compuestos adicionales de fórmula (I) (véase, por ejemplo, O’Brien, C. J. y Organ, M. G. Angew. Chem. Int. Ed. (2007), 46, 2768-2813; Suzuki, A. Journal of Organometallic Chemistry (2002), 653, 83; Miyaura N. y Suzuki, A. Chem. Rev. (1995), 95, 2457-2483).
Los compuestos de fórmula (I) en la que G es alquilo de C1-C8, haloalquilo de C2-C8, fenil-alquilo de C1-C8 (en el que el fenilo puede estar opcionalmente sustituido con alquilo de C1-C3, haloalquilo de C1-C3, alcoxi de C1-C3, haloalcoxi de C1-C3, alquil C1-C3-tio, alquil C1-C3-sufinilo, alquil C1-C3-sulfonilo, halógeno, ciano o con nitro), heteroaril-alquilo de C1-C8 (en el que el heteroarilo puede estar opcionalmente sustituido con alquilo de C1-C3, haloalquilo de C1-C3, alcoxi de C1-C3, haloalcoxi de C1-C3, alquil C1-C3-tio, alquil C1-C3-sulfinilo, alquil C1-C3-sulfonilo, halógeno, ciano o con nitro), alquenilo de C3-C8, haloalquenilo de C3-C8, alquinilo de C3-C8, C(Xa)-Ra, C(Xb)-Xc-Rb, C(Xd)-N(Rc)-Rd, SO2-Re, -P(Xe)(Rf)-Rg o CH2-Xf-Rh, en los que Xa, Xb, Xc, Xd, Xe, Xf, Ra, Rb, Rc, Rd, Re, Rf, Rg y Rh son como se definen anteriormente, se puede preparar tratando compuestos de fórmula (A), que son compuestos de fórmula (I) en la que G es H, con un reactivo G-Z, en el que G-Z es un agente alquilante tal como un haluro de alquilo (la definición de haluros de alquilo incluye haluros de alquilo de C1-C8 sencillos tales como yoduro de metilo y yoduro de etilo, haluros de alquilo sustituidos tales como éteres de clorometil-alquilo, Cl-CH2-Xf-Rh, en los que Xf es oxígeno, y sulfuros de clorometil-alquilo Cl-CH2-Xf-Rh, en los que Xf es azufre), un sulfonato de alquilo C1-C8, o un sulfato de dialquilo de C1-C8, o con un haluro de alquenilo de C3-C8, o con un haluro de alquinilo de C3-C8, o con un agente acilante tal como un ácido carboxílico, HO-C(Xa)Ra, en el que Xa es oxígeno, un cloruro de ácido, Cl-C(Xa)Ra, en el que Xa es oxígeno, o anhídrido de ácido, [RaC(Xa)]2O, en el que Xa es oxígeno, o un isocianato, RcN=C=O, o un cloruro de carbamoilo, Cl-C(Xd)-N(Rc)-Rd (en el que Xd es oxígeno y con la condición de que ni Rc ni Rd sean hidrógeno), o un cloruro de tiocarbamoilo Cl-C(Xd)-N(Rc)-Rd (en el que Xd es azufre y con la condición de que ni Rc ni Rd sean hidrógeno) o un cloroformiato, Cl-C(Xb)-Xc-Rb, (en el que Xb y Xc son oxígeno), o un clorotioformiato ClC(Xb)-Xc-Rb (en el que Xb es oxígeno y Xc es azufre), o un cloroditioformiato Cl-C(Xb)-Xc-Rb, (en el que Xb y Xc son azufre), o un isotiocianato, RcN=C=S, o por tratamiento secuencial con disulfuro de carbono y un agente alquilante, o con un agente fosforilante tal como un cloruro de fosforilo, Cl-P(Xe)(Rf)-Rg, o con un agente sulfonilante tal como un cloruro de sulfonilo Cl-SO2-Re, preferiblemente en presencia de al menos un equivalente de base.
Se pueden formar compuestos isoméricos de fórmula (I). Por ejemplo, los compuestos de fórmula (A) pueden dar lugar a dos compuestos isoméricos de fórmula (I), o a mezclas isoméricas de compuestos de fórmula (I). Esta invención cubre ambos compuestos isoméricos de fórmula (I), junto con mezclas de estos compuestos en cualquier relación.
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Los compuestos de fórmula (F) son compuestos conocidos, o se pueden preparar a partir de compuestos conocidos mediante métodos conocidos.
Los compuestos de fórmula (J) se pueden preparar, por ejemplo, por métodos análogos a los descritos por Ballini, R. 5 et al. Synthesis (2002), (5), 681-685; Bergmeier, S. C. e Ismail, K. A. Synthesis (2000), (10), 1369-1371; Groutas, W.
C. et al. J. Med. Chem. (1989), 32 (7), 1607-11 y Bernhard, K. y Lincke, H. Helv. Chim. Acta (1946), 29, 1457-1466.
Los compuestos de fórmula (G) o compuestos de fórmula (H) se pueden preparar a partir de un compuesto de fórmula (J) mediante tratamiento con un alcohol alquílico, R’’’-OH, en presencia de una base, tal como dimetilaminopiridina o un alcóxido de metal alcalino (véanse, por ejemplo, S. Buser y A. Vasella, Helv. Chim. Acta,
10 (2005), 88, 3151, M. Hart et al., Bioorg. Med. Chem. Letters, (2004), 14, 1969), seguido de tratamiento del ácido resultante con un agente clorante tal como cloruro de oxalilo o cloruro de tionilo en condiciones conocidas (véanse, por ejemplo, C. Santelli-Rouvier. Tetrahedron Lett., (1984), 25, (39), 4371; D. Walba y M. Wand, Tetrahedron Lett., (1982), 23 (48), 4995; J. Cason, Org. Synth. Coll. Vol. III, (169), 1955).
imagen14
15 Los compuestos de fórmula (G) y los compuestos de fórmula (H) se pueden obtener a partir de compuestos conocidos por métodos conocidos. Por ejemplo, los métodos análogos para obtener compuestos de fórmula (G) y compuestos de fórmula (H) se describen por Bergmeier, S. C. e Ismail, K. A. Synthesis (2000), (10), 1369-1371.
En un enfoque adicional, los compuestos de fórmula (I) se pueden preparar tratando compuestos de fórmula (K) con compuestos de fórmula (L) en la que LG es un grupo saliente tal como halógeno (preferiblemente yoduro o bromuro)
20 o un alcohol activado (preferiblemente mesilato o tosilato) en condiciones básicas. Las bases adecuadas incluyen diisopropilamiduro de litio, hexametildisilazida sódica, terc-butóxido de potasio, y la reacción se lleva a cabo preferiblemente en un disolvente adecuado (tal como tetrahidrofurano) a una temperatura entre -80ºC y 30ºC.
imagen15
Los compuestos de fórmula (L) son conocidos, o se pueden obtener a partir de compuestos conocidos por métodos 25 conocidos.
5
10
15
20
25
30
35
Los compuestos de fórmula (K) son compuestos conocidos o se pueden obtener a partir de compuestos conocidos por métodos conocidos (véanse, por ejemplo, Song, Y. S. S. et al. Tetrahedron Lett. (2005), 46 (46), 5987-5990; Kuethe, J. T. et al. J. Org. Chem. (2002), 67 (17), 5993-6000).
De manera alternativa, los compuestos de fórmula (K), en los que G es alquilo de C1-C6, se pueden preparar por alquilación de compuestos de fórmula (K), en los que G es hidrógeno, en condiciones conocidas o por métodos conocidos (véase, por ejemplo, Eberhardt, U. et al. Chem. Ber. (1983), 116 (1), 119-135).
Los compuestos de fórmula (K) en los que G es hidrógeno, son conocidos, o se pueden preparar a partir de compuestos conocidos mediante métodos conocidos (véanse, por ejemplo, Nguyen, H. N. et al. J. Am. Chem. Soc. (2003), 125 (39), 11818-11819; Bonjoch, J. et al. Tetrahedron (2001), 57(28), 6011-6017; Fox, J. M. et al. J. Am. Chem. Soc. (2000), 122(7), 1360-1370; documentos US4338122; US4283348).
De manera alternativa, los compuestos de fórmula (I) en los que R5 y R6 forman un enlace se pueden preparar a partir de compuestos de fórmula (M) mediante métodos conocidos (véanse, por ejemplo, Habib-Zahmani, H. et al. Synlett (2007), (7), 1037-1042; Nagaoka, H. et al. Tetrahedron Letters (1985), 26 (41), 5053-5056; Nagaoka, H. et al.
J. Am. Chem. Soc. (1986), 108 (16), 5019-5021; Zuki, M. et al. Bull. Chem. Soc. Japan (1988), 61(4), 1299-1312; Enholm, E. J. et al. J. Org. Chem. (1996), 61 (16), 5384-5390; Clive, D. L. J. et al. Tetrahedron (2001), 57 (18), 38453858; Bartoli, G. et al. J. Org. Chem. (2002), 67 (25), 9111-9114. Jung, M. E. et al. Chem. Comm. (2003), (2), 196197; documentos EP1433772; JP2004203844; IN 194295).
imagen16
en la que R5 y R6 forman un enlace
Los compuestos de fórmula (M) se pueden preparar tratando compuestos de fórmula (K) con compuestos de fórmula
(N) en condiciones básicas. Las bases adecuadas incluyen diisopropilamiduro de litio, hexametildisilazida sódica, terc-butóxido de potasio, y la reacción se lleva a cabo preferiblemente en un disolvente adecuado (tal como tetrahidrofurano) a una temperatura entre -80ºC y 30ºC.
imagen17
Los compuestos de fórmula (N) son compuestos conocidos, o se pueden obtener a partir de compuestos conocidos por métodos conocidos.
Los compuestos de fórmula (I) (en la que G es alquilo de C1-4) se pueden preparar haciendo reaccionar compuestos de fórmula (O) (en la que G es alquilo de C1-4, y Hal es halógeno, preferiblemente bromo o yodo) con ácidos arilborónicos, Ar-B(OH)2, de fórmula (P) en presencia de un catalizador de paladio adecuado (por ejemplo 0,00150% de acetato de paladio(II) con respecto al compuesto (O)) y una base (por ejemplo 1 a 10 equivalentes de fosfato de potasio con respecto al compuesto (O)) y preferiblemente en presencia de un ligando adecuado (por ejemplo 0,001-50% de (2-diciclohexilfosfino)-2’,6’-dimetoxibifenilo con respecto al compuesto (O)), y en un disolvente adecuado (por ejemplo tolueno o 1,2-dimetoxietano), preferiblemente entre 25ºC y 200ºC bajo calentamiento convencional o bajo irradiación de microondas (véanse, por ejemplo, Song, Y. S. S. et al. Tetrahedron Lett. (2005), 46 (46), 5987-5990; Kuethe, J. T. et al. J. Org. Chem. (2002), 67(17), 5993-6000).
imagen18
Un compuesto de fórmula (O) se puede preparar halogenando un compuesto de fórmula (Q), seguido de la alquilación del haluro resultante de fórmula (R) con un haluro de alquilo de C1-4 u ortoformiato de trialquilo de C1-4 en condiciones conocidas, por ejemplo mediante los procedimientos de Shepherd R. G. et al. J. Chem. Soc. Perkin Trans. 1 (1987), 2153-2155 y Lin Y.-L. et al. Bioorg. Med. Chem. (2002), 10, 685-690. Como alternativa, los compuestos de fórmula (O) se pueden preparar alquilando un compuesto de fórmula (Q) con un haluro de alquilo de C1-4 o un ortoformiato de trialquilo de C1-4, y halogenando la enona resultante de fórmula (S) en condiciones conocidas (véanse, por ejemplo, Song, Y. S. et al. Tetrahedron Lett. (2005), 46 (36), 5987-5990; Kuethe, J. T. et al.
J. Org. Chem. (2002), 67(17), 5993-6000; Belmont, D. T. et al. J. Org. Chem. 1985, 50 (21), 4102-4107).
imagen19
Los compuestos de fórmula (S) se pueden preparar tratando compuestos de fórmula (T) con compuestos de fórmula
(L) en los que LG es un grupo saliente tal como halógeno (preferibemente yoduro o bromuro) o una alcohol activado (preferibemente mesilato o tosilato) en condiciones básicas. Las bases adecuadas incluyen diisopropilamiduro de litio, hexametildisilazida sódica, terc-butóxido de potasio, y la reacción se lleva a cabo preferibemente en un
15 disolvente adecuado (tal como terahidrofurano) a una temperatura entre -80ºC y 30ºC (véanse, por ejemplo, Gulias,
M. et al. Org. Lett. (2003), 5(11), 1975-1977; Altenbach, R. J. et al. J. Med. Chem. (2006), 49 (23), 6869-6887; Snowden, R. L. Tetrahedron (1986), 42 (12), 3277-90; Oppolzer, W. et al. Helv. Chim. Acta (1980), 63 (4), 788-92; Mellor, M. et al. Synth. Commun. 1979, 9 (1), 1-4).
imagen20
imagen21
imagen22
imagen23
El reactivo órgano-plumbífero de fórmula (X) se puede preparar a partir de un ácido borónico de fórmula (P), un estannano de fórmula (Y), en la que R’’’’’ es alquilo de C1-C4, o mediante plumbación directa de un compuesto de fórmula (Z) con tetraacetato de plomo según procedimientos conocidos.
imagen24
Otros compuestos de fórmula (A) se pueden preparar haciendo reaccionar compuestos de fórmula (Q) con un compuesto de triarilbismuto adecuado, en condiciones descritas, por ejemplo, por Fedorov A. U. et al., Russ. Chem. Bull. Int. Ed., (2005), 54 (11), 2602, y por Koech P. et al., J. Am. Chem. Soc., (2004), 126 (17), 5350 y las referencias allí.
10 Compuestos adicionales de fórmula (A) se pueden preparar haciendo reaccionar un iluro de yodonio de fórmula (AA), en la que Ar es un grupo fenilo opcionalmente sustituido, y un ácido arilborónico de fórmula (P), en presencia de un catalizador de paladio adecuado, una base y un disolvente adecuado.
imagen25
Los catalizadores de paladio adecuados son generalmente complejos de paladio(II) o paladio(0), por ejemplo
15 dihaluros de paladio(II), acetato de paladio(II), sulfato de paladio(II), dicloruro de bis(trifenilfosfina)paladio(II), dicloruro de bis(triciclopentilfosfina)paladio(II), dicloruro de bis(triciclohexilfosfina)paladio(II), bis(dibencilidenacetona)paladio(0) o tetraquis(trifenilfosfina)paladio(0). El catalizador de paladio también se puede preparar in situ a partir de compuestos de paladio(II) o paladio(0) complejándolos con los ligandos deseados, por ejemplo combinando la sal de paladio(II) a complejar, por ejemplo dicloruro de paladio(II) (PdCl2) o acetato de
20 paladio(II) (Pd(OAc)2), junto con el ligando deseado, por ejemplo trifenilfosfina (PPh3), triciclopentilfosfina, triciclohexilfosfina, 2-diciclohexilfosfino-2’,6’-dimetoxibifenilo o 2-diciclohexilfosfino-2’,4’,6’-triisopropilbifenilo y el
disolvente seleccionado, con un compuesto de fórmula (AA), el ácido arilborónico de fórmula (P) y una base. También son adecuados los ligandos bidendatos, por ejemplo 1,1’-bis(difenilfosfino)ferroceno o 1,2bis(difenilfosfino)etano. Calentando el medio de reacción, el complejo de paladio(II) o complejo de paladio(0) deseado para la reacción de acoplamiento C-C se forma así in situ, y después inicia la reacción de acoplamiento C
5 C.
Los catalizadores de paladio se usan en una cantidad de 0,001 a 50% en moles, preferiblemente en una cantidad de 0,1 a 15% en moles, basado en el compuesto de fórmula (AA). La reacción también se puede llevar a cabo en presencia de otros aditivos, tales como sales de tetraalquilamonio, por ejemplo bromuro de tetrabutilamonio. Preferiblemente, el catalizador de paladio es acetato de paladio, la base es hidróxido de litio, y el disolvente es 1,2
10 dimetoxietano acuoso.
Un compuesto de fórmula (AA) se puede preparar a partir de un compuesto de fórmula (Q) mediante tratamiento con un reactivo de yodo hipervalente, tal como (diacetoxi)yodobenceno o un yodosilbenceno, y una base tal como carbonato de sodio acuoso, hidróxido de litio o hidróxido de sodio en un disolvente tal como agua o un alcohol acuoso tal como etanol acuoso, según los procedimientos de Schank K. et al., Synthesis, (1983), 392, Moriarty R. M.
15 et al., J. Am. Chem. Soc, (1985), 107, 1375, o de Yang Z. et al., Org. Lett., 2002, 4 (19), 3333.
imagen26
De manera alternativa, los compuestos de fórmula (I) se pueden preparar por reacción de compuestos heteroaromáticos (preferiblemente tiofeno, pirrol o furano) con compuestos de fórmula (AB)
imagen27
en la que R5 y R6 forman un enlace
Los compuestos de fórmula (AB) se pueden preparar a partir de compuesto (AH), en los que LG es un grupo saliente tal como halógeno (preferiblemente yoduro o bromuro), un alcohol activado (preferiblemente mesilato o tosilato) en condiciones básicas por métodos conocidos (vénase, por ejemplo, Drege, E. et al. Tetrahedron Letters (2005), 46(42), 7263-7266 y Drege, E. et al. Eur. J. Org. Chem. (2006), (21), 4825-4840).
imagen28
en la que R5 y R6 forman un enlace
Los compuestos de fórmula (AC) se pueden preparar, por ejemplo, a partir de compuestos de fórmula (K) con compuestos de fórmula (AE) en condiciones básicas, seguido de una activación del grupo hidroxilo de los compuestos (AD). Las bases adecuadas incluyen diisopropilamiduro de litio, hexametildisilazida sódica, terc
30 butóxido de potasio, y la reacción se lleva a cabo preferiblemente en un disolvente adecuado (tal como tetrahidrofurano) a una temperatura entre -80ºC y 30ºC (véanse, por ejemplo, Drege, E. et al. Tetrahedron Letters (2005), 46 (42), 7263-7266 y Drege, E. et al. Eur. J. Org. (2006), (21), 4825-4840).
imagen29
imagen30
imagen31
imagen32
imagen33
imagen34
imagen35
imagen36
imagen37
imagen38
imagen39
imagen40
imagen41
imagen42
imagen43
imagen44
imagen45
imagen46
imagen47
imagen48
3,80
0,00 100 1,30
4,80
0,00 100 1,30
5,00
90,0 10,0 1,30
6,00
90,0 10,0 1,30
Disolvente A: H2O con 0,05% de HCOOH Disolvente B: CH3CN con 0,05% de HCOOH
Tabla T1
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T1
δ ppm 1,02-1,12 (m, 6H), 2,21-2,46 (m, 10H), 2,55-3,55 (m, 5H), 5,88-5,97 (m, 1H), 6,89-6,98 (m, 2H), 10,12 (s, 1H)
T2
δ ppm 1,94 (s, 3H) 2,09 (s, 3H) 2,27 (s, 3H) 2,45 (d, 1H) 2,71 -2,85 (m, 3H) 2,99 (dd, 1H) 6,31 (s, 1H) 6,91 (d, 2H) 7,29 (s, 1H) 7,36 (s, 1H)
T3
δ ppm 1,84 -2,15 (m, 6H) 2,22 -2,42 (m, 7H) 2,91 -3,19 (m, 3H) 3,13 -3,49 (m, 1H) 5,82 -6,6.98 (m, 1H) 6,82 -6,91 (m, 2H) 10,22 (s, 1H)
T4
δ ppm 1,98 (s, 3H) 2,07 (s, 3H) 2,24 (s, 3H) 2,27 (s, 3H) 2,52 -2,63 (m, 1H) 2,73 -2,89 (m, 2H) 3,05 -3,12 (m, 1H) 3,16 (dd, 1H) 5,85 (d, 1H) 5,95 (d, 1H) 6,89 (d, 2H)
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T5
δ ppm 1,92 (s, 3H) 2,08 (s, 3H) 2,26 (s, 3H) 2,61 -2,67 (m, 1H) 2,84 (dd, 1H) 2,96 -3,09 (m, 2H) 3,38 (dd, 1H) 6,48 (s, 1H) 6,89 (d, 2H) 7,16 -7,26 (m, 2H) 7,39 (d, 1H) 7,49 (d, 1H)
T6
δ ppm 2,11 (s, 3H) 2,15 (s, 6H) 3,37 (s, 2H) 6,60 (s, 1H) 6,92 -6,98 (m, 3H) 7,47 (s, 1H) 7,64 (s, 1H)
T7
δ ppm 1,9 (s, 3H), 2,19 (s, 3H), 2,2 (s, 3H), 2,5 (dd, 1H), 2,8 (dd, 2H), 3,03 (m, 2H), 3,3 (s, 3H), 6,78 (d, 1H), 6,83 (s, 1H), 6,85 (d, 2H), 7,10 (d, 1H)
T8
δ ppm 2,12 (s, 6H) 2,30 (s, 3H) 3,50 (d, 2H) 6,85 (s, 1H) 6,95 (m, 3H) 7,37 (d, 1H) 7,53 (d, 1H)
T9
δ ppm 2,12 (s, 6H) 2,29 (s, 3H) 2,36 (s, 3H) 3,49 (d, 2H) 6,09 (d, 1H) 6,43 (d, 1H) 6,78 (s, 1H) 6,94 (s, 2H)
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T10
LC-MS (Método C) ES: 340, 338 (M-H). rt = 5,09 minutos
T11
LC-MS (Método C) ES: (M-H)= 306. rt = 3,92 minutos
T12
LC-MS (Método C) ES+: MH+ = 326. rt = 3,53 minutos
T13
LC-MS (Método C) ES+: MH+ = 308. rt = 2,42 minutos
T14
LC-MS (Método C) ES+: MH+ = 306. rt = 2,94 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T15
LC-MS (Método C) ES+: MH+ = 306. rt = 2,56 minutos
T16
LC-MS (Método C) ES+: MH+ = 306. rt = 3,24 minutos
T17
imagen49 LC-MS (Método C) ES+: MH+ = 308. rt = 2,96 minutos
T18
imagen50 LC-MS (Método C) ES: 340, 338 (M-H). rt = 3,98 minutos
T19
LC-MS (Método C) ES: (M-H)= 321. rt = 4,02 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T20
LC-MS (Método C) ES: (M-H)= 371. rt = 3,86 minutos
T21
LC-MS (Método A) ES+: MH+ = 309 r.t. = 1,63m
T22
LC-MS (Método C) ES+: 372, 370 (M+H)+ rt = 3,41 minutos
T23
LC-MS (Método C) ES+: MH+ = 370. rt = 3,59 minutos
T24
LC-MS (Método C) ES+: MH+ = 294. rt = 2,58 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T25
LC-MS (Método C) ES: (M-H)= 320. rt = 2,81 minutos
T26
LC-MS (Método C) ES+: MH+ = 320. rt = 2,75 minutos
T27
LC-MS (Método C) ES: 384, 382 (M-H). rt = 4,37 minutos
T28
LC-MS (Método C) ES: 340, 338 (M-H). rt = 4,27 minutos
T29
LC-MS (Método C) ES+: 374, 372 (M+H)+ rt = 3,2 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T30
LC-MS (Método C) ES: 326, 324 (M-H). rt= 3,26 & 3,91 minutos
T31
LC-MS (Método C) ES+: MH+ = 310. rt=2,88&3,66 minutos
T32
LC-MS (Método C) ES+: MH+ = 312. rt = 2,72 minutos
T33
LC-MS (Método C) ES: 328, 326 (M-H). rt = 3,03 minutos
T34
LC-MS (Método C) ES+: MH+ = 326. rt = 3,71 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T35
LC-MS (Método C) ES+: MH+ = 324. rt = 4,01 minutos
T36
LC-MS (Método C) ES+: MH+ = 322. rt = 2,78 minutos
T37
LC-MS (Método C) ES+: MH+ = 320. rt= 2,84 & 3,91 minutos
T38
δ ppm (CD3OD) 1,92 (s, 3H), 2,04 (s, 3H), 2,24 (s, 3H), 2,45 (dd, 1H), 2,85 (dd, 1H), 3,10 (dd, 1H), 3,20 (m, 1H), 3,30 (dd, 1H), 6,85 (s, 1H), 6,87 (s, 1H), 7,92 (dd, 1H), 8,46 (d, 1H), 8,68 (d, 1H), 8,76 (s, 1H)
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T39
LC-MS (Método A) ES+: MH+= 385 r.t. = 1,91 m
T40
LC-MS (Método C) ES: (M-H)= 336. rt = 3,86 minutos
T41
LC-MS (Método C) ES+: MH+ = 336. rt = 4,12 & 4,24 minutos
T42
LC-MS (Método C) ES: (M-H)= 346. rt = 3,46 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T43
LC-MS (Método C) ES+: MH+ = 382. rt = 4,33 minutos
T44
LC-MS (Método C) ES+: MH+ = 384. rt = 3,65 minutos
T45
LC-MS (Método C) ES+: 386, 384 (M+H)+ rt = 4,36 minutos
T46
LC-MS (Método C) ES+: MH+ = 336. rt = 3,21 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T47
LC-MS (Método C) ES+: MH+ = 350. rt = 3,43 minutos
T48
LC-MS (Método C) ES+: MH+ = 350. rt = 3,51 minutos
T49
LC-MS (Método C) ES+: MH+ = 393. rt = 3,15 minutos
T50
LC-MS (Método C) ES+: MH+ = 320. rt = 3,46 minutos
T51
LC-MS (Método C) ES+: MH+ = 322. rt = 3,05 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T52
LC-MS (Método C) ES+: MH+ = 322. rt = 2,94 minutos
T53
LC-MS (Método C) ES+: MH+ = 348. rt = 3,34 minutos
T54
LC-MS (Método C) ES+: MH+ = 324. rt = 2,99 minutos
T55
LC-MS (Método C) ES+: MH+ = 326. rt = 3,68 minutos
T56
LC-MS (Método C) ES+: MH+ = 348. rt = 3,33 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T57
LC-MS (Método C) ES+: MH+ = 331. rt = 4,03 minutos
T58
LC-MS (Método C) ES+: MH+ = 384. rt = 4,17 minutos
T59
imagen51 LC-MS (Método A) ES+: MH+ = 384. rt = 1,80 minutos
T60
LC-MS (Método A) ES+: MH+ = 368. rt = 1,51 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T61
LC-MS (Método A) ES+: MH+ = 416. rt = 1,61 minutos
T62
LC-MS (Método C) ES+: MH+ = 402. rt = 3,81 minutos
T63
LC-MS (Método C) ES+: MH+ = 400. rt = 4,48 minutos
T64
LC-MS (Método C) ES+: MH+ = 384. rt = 3,99 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T65
LC-MS (Método C) ES+: MH+ = 318. rt = 2,98 minutos
T66
LC-MS (Método C) ES+: MH+ = 333. rt = 3,56 minutos
T67
LC-MS (Método C) ES+: 386, 384 (M+H)+ rt= 4,22 & 4,33 minutos
T68
LC-MS (Método C) ES: 340, 338 (M-H). rt = 3,93 minutos
T69
LC-MS (Método C) ES+: MH+ = 368. rt = 3,87 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T70
LC-MS (Método C) ES+: MH+ = 386. rt = 3,86 minutos
T71
LC-MS (Método C) ES+: MH+ = 388. rt = 3,59 minutos
T72
LC-MS (Método C) ES+: MH+ = 334. rt = 3,39 minutos
T73
LC-MS (Método C) ES+: MH+ = 336. rt = 3,16 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T74
LC-MS (Método C) ES+: MH+ = 336. rt = 3,37 minutos
T75
LC-MS (Método C) ES+: MH+ = 319. rt = 2,49 minutos
T76
LC-MS (Método C) ES+: MH+ = 322. rt = 3,08 minutos
T77
LC-MS (Método C) ES: (M-H)= 346. rt = 3,78 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T78
LC-MS (Método C) ES+: MH+ = 348. rt = 3,83 minutos
T79
LC-MS (Método C) ES+: MH+ = 386. rt=4,22&4,33 minutos
T80
LC-MS (Método C) ES+: MH+ = 356. rt = 3,99 minutos
T81
LC-MS (Método B) ES+: MH+ = 376. rt = 1,44 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T82
LC-MS (Método B) ES+: MH+ = 371. rt = 1,41 minutos
T83
LC-MS (Método B) ES+: MH+ = 355. rt = 1,46 minutos
T84
LC-MS (Método B) ES+: MH+ = 347, 349. rt = 1,58 minutos
T85
LC-MS (Método B) ES+: MH+ = 372, 374. rt = 1,54 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T86
LC-MS (Método B) ES+: MH+ = 379. rt = 1,42 minutos
T87
LC-MS (Método B) ES+: MH+ = 326. rt = 1,19 minutos
T88
imagen52 LC-MS (Método B) ES+: MH+ = 370. rt = 1,65 minutos
T89
LC-MS (Método B) ES+: MH+ = 369. rt = 1,52 minutos
T90
LC-MS (Método C) ES+: 386, 384 (M+H)+ rt = 4,24 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T91
LC-MS (Método C) ES+: MH+ = 348. rt = 3,83 minutos
T92
LC-MS (Método C) ES+: MH+ = 352. rt = 2,8 minutos
T93
LC-MS (Método C) ES+: MH+ = 352. rt = 2,69 minutos
T94
LC-MS (Método C) ES+: MH+ = 352. rt = 3,02 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T95
LC-MS (Método C) ES+: MH+ = 348. rt = 3,8 minutos
T96
LC-MS (Método C) ES+: MH+ = 350. rt= 3,13 & 3,59 minutos
T97
LC-MS (Método C) ES+: MH+ = 352. rt=2,89&3,00 minutos
T98
LC-MS (Método C) ES+: MH+ = 354. rt = 3,83 minutos
T99
imagen53 LC-MS (Método C) ES+: MH+ = 340. rt = 3,9 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
T100
LC-MS (Método C) ES+: MH+ = 338. rt = 2,14 minutos
T101
LC-MS (Método C) ES+: MH+ = 354. rt = 3,74 minutos
T102
LC-MS (Método C) ES+: MH+ = 354. rt = 3,64 minutos
T103
LC-MS (Método C) ES+: MH+ = 354. rt = 3,49 minutos
Tabla P1
imagen54
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
P1
δ ppm 1,92 (s, 3H) 2,05 (s, 3H) 2,10 (s, 3H) 2,20 (s, 3H) 2,26 (s, 3H) 2,45 (dd, 1H) 2,82 (dd, 1H) 3,17 (ddd, 1H) 4,71 (d, 1H) 4,95 (s, 1H) 6,12 (s, 1H) 6,87 (s, 2H)
P2
δ ppm 1,12 (s, 9H), 2,09 (s, 6H) 2,26 (s, 3H) 3,81 (s, 2H) 6,62 (s, 1H) 6,83 (s, 2H) 7,41 (s, 1H) 7,52 (s, 1H) 7,78 (s, 1H)
P3
LC-MS (Método A) ES+: MH+ = 326 r.t. = 1,54m
P4
LC-MS (Método C) ES+: MH+ = 392. rt = 3,71 minutos
P5
LC-MS (Método C) ES+: MH+ = 442. rt = 4,54 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
P6
LC-MS (Método A) ES+: MH+ = 488. rt = 2,23 minutos
P7
LC-MS (Método C) ES+: MH+ = 339. rt = 3,24 minutos
P8
LC-MS (Método C) ES+: MH+ = 406. rt = 3,64 minutos
P9
LC-MS (Método C) ES+: MH+ = 406. rt = 3,61 minutos
P10
LC-MS (Método C) ES+: MH+ = 322. rt = 2,84 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
P11
LC-MS (Método C) ES+: MH+ = 338. rt = 3,17 minutos
P12
LC-MS (Método C) ES+: MH+ = 352. rt = 4,26 minutos
P13
LC-MS (Método C) ES+: MH+ = 473. rt = 3,73 minutos
P14
LC-MS (Método C) ES+: MH+ = 366. rt = 3,09 minutos
Compuesto número
Estructura RMN 1H (CDCl3 excepto que es señale) u otro dato físico
P15
LC-MS (Método C) ES+: MH+ = 406. rt = 3,35 minutos
P16
LC-MS (Método C) ES+: MH+ = 350. rt = 4,59 minutos
Los compuestos de las siguientes Tablas 1 a 58 se pueden obtener de una manera análoga. La Tabla 1 cubre 1731 compuestos del tipo estructural T-1:
imagen55
en los que R1 y R3 son metilo, y R2 y R4 son hidrógeno, y en los que R5, R6, R7, R8, R9 y HetAr son como se definen en la tabla a continuación:
Compuesto número
R5 R6 R7 R8 R9 HetAr
1
H H H H H 2-piridilo
2
H H H H H 3-fluoro-2-piridilo
3
H H H H H 4-fluoro-2-piridilo
4
H H H H H 5-fluoro-2-piridilo
5
H H H H H 6-fluoro-2-piridilo
6
H H H H H 3-cloro-2-piridilo
7
H H H H H 4-cloro-2-piridilo
8
H H H H H 5-cloro-2-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
9
H H H H H 6-cloro-2-piridilo
10
H H H H H 3-metil-2-piridilo
11
H H H H H 4-metil-2-piridilo
12
H H H H H 5-metil-2-piridilo
13
H H H H H 6-metil-2-piridilo
14
H H H H H 3-trifluorometil-2-piridilo
15
H H H H H 4-trifluorometil-2-piridilo
16
H H H H H 5-trifluorometil-2-piridilo
17
H H H H H 6-trifluorometil-2-piridilo
18
H H H H H 3-metoxi-2-piridilo
19
H H H H H 4-metoxi-2-piridilo
20
H H H H H 5-metoxi-2-piridilo
21
H H H H H 6-metoxi-2-piridilo
22
H H H H H 3-trifluorometoxi-2-piridilo
23
H H H H H 4-trifluorometoxi-2-piridilo
24
H H H H H 5-trifluorometoxi-2-piridilo
25
H H H H H 6-trifluorometoxi-2-piridilo
26
H H H H H 3-ciano-2-piridilo
27
H H H H H 4-ciano-2-piridilo
28
H H H H H 5-ciano-2-piridilo
29
H H H H H 6-ciano-2-piridilo
30
H H H H H 3-nitro-2-piridilo
31
H H H H H 4-nitro-2-piridilo
32
H H H H H 5-nitro-2-piridilo
33
H H H H H 6-nitro-2-piridilo
34
H H H H H 3-metanosulfonil-2-piridilo
35
H H H H H 4-metanosulfonil-2-piridilo
36
H H H H H 5-metanosulfonil-2-piridilo
37
H H H H H 6-metanosulfonil-2-piridilo
38
H H H H H 3-piridilo
39
H H H H H 2-fluoro-3-piridilo
40
H H H H H 4-fluoro-3-piridilo
41
H H H H H 5-fluoro-3-piridilo
42
H H H H H 6-fluoro-3-piridilo
43
H H H H H 2-cloro-3-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
44
H H H H H 4-cloro-3-piridilo
45
H H H H H 5-cloro-3-piridilo
46
H H H H H 6-cloro-3-piridilo
47
H H H H H 2-bromo-3-piridilo
48
H H H H H 4-bromo-3-piridilo
49
H H H H H 5-bromo-3-piridilo
50
H H H H H 6-bromo-3-piridilo
51
H H H H H 2-metoxi-3-piridilo
52
H H H H H 4-metoxi-3-piridilo
53
H H H H H 5-metoxi-3-piridilo
54
H H H H H 6-metoxi-3-piridilo
55
H H H H H 2-trifluorometoxi-3-piridilo
56
H H H H H 4-trifluorometoxi-3-piridilo
57
H H H H H 5-trifluorometoxi-3-piridilo
58
H H H H H 6-trifluorometoxi-3-piridilo
59
H H H H H 2-metil-3-piridilo
60
H H H H H 4-metil-3-piridilo
61
H H H H H 5-metil-3-piridilo
62
H H H H H 6-metil-3-piridilo
63
H H H H H 2-trifluorometil-3-piridilo
64
H H H H H 4-trifluorometil-3-piridilo
65
H H H H H 5-trifluorometil-3-piridilo
66
H H H H H 6-trifluorometil-3-piridilo
67
H H H H H 2-ciano-3-piridilo
68
H H H H H 4-ciano-3-piridilo
69
H H H H H 5-ciano-3-piridilo
70
H H H H H 6-ciano-3-piridilo
71
H H H H H 2-nitro-3-piridilo
72
H H H H H 4-nitro-3-piridilo
73
H H H H H 5-nitro-3-piridilo
74
H H H H H 6-nitro-3-piridilo
75
H H H H H 2-metanosulfonil-3-piridilo
76
H H H H H 4-metanosulfonil-3-piridilo
77
H H H H H 5-metanosulfonil-3-piridilo
78
H H H H H 6-metanosulfonil-3-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
79
H H H H H 4-piridilo
80
H H H H H 2-fluoro-4-piridilo
81
H H H H H 3-fluoro-4-piridilo
82
H H H H H 2-cloro-4-piridilo
83
H H H H H 3-cloro-4-piridilo
84
H H H H H 2-bromo-4-piridilo
85
H H H H H 3-bromo-4-piridilo
86
H H H H H 2-metoxi-4-piridilo
87
H H H H H 3-metoxi-4-piridilo
88
H H H H H 2-trifluorometoxi-4-piridilo
89
H H H H H 3-trifluorometoxi-4-piridilo
90
H H H H H 2-metil-4-piridilo
91
H H H H H 3-metil-4-piridilo
92
H H H H H 2-trifluorometil-4-piridilo
93
H H H H H 3-trifluorometil-4-piridilo
94
H H H H H 2-ciano-4-piridilo
95
H H H H H 3-ciano-4-piridilo
96
H H H H H 2-nitro-4-piridilo
97
H H H H H 3-nitro-4-piridilo
98
H H H H H 2-metanosulfonil-4-piridilo
99
H H H H H 3-metanosulfonil-4-piridilo
100
H H H H H 2-piridazinilo
101
H H H H H 4-fluoro-2-piridazinilo
102
H H H H H 5-fluoro-2-piridazinilo
103
H H H H H 6-fluoro-2-piridazinilo
104
H H H H H 4-cloro-2-piridazinilo
105
H H H H H 5-cloro-2-piridazinilo
106
H H H H H 6-cloro-2-piridazinilo
107
H H H H H 4-bromo-2-piridazinilo
108
H H H H H 5-bromo-2-piridazinilo
109
H H H H H 6-bromo-2-piridazinilo
110
H H H H H 4-metoxi-2-piridazinilo
111
H H H H H 5-metoxi-2-piridazinilo
112
H H H H H 6-metoxi-2-piridazinilo
113
H H H H H 4-trifluorometoxi-2-piridazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
114
H H H H H 5-trifluorometoxi-2-piridazinilo
115
H H H H H 6-trifluorometoxi-2-piridazinilo
116
H H H H H 4-metil-2-piridazinilo
117
H H H H H 5-metil-2-piridazinilo
118
H H H H H 6-metil-2-piridazinilo
119
H H H H H 4-trifluorometil-2-piridazinilo
120
H H H H H 5-trifluorometil-2-piridazinilo
121
H H H H H 6-trifluorometil-2-piridazinilo
122
H H H H H 4-ciano-2-piridazinilo
123
H H H H H 5-ciano-2-piridazinilo
124
H H H H H 6-ciano-2-piridazinilo
125
H H H H H 4-nitro-2-piridazinilo
126
H H H H H 5-nitro-2-piridazinilo
127
H H H H H 6-nitro-2-piridazinilo
128
H H H H H 4-metanosulfonil-2-piridazinilo
129
H H H H H 5-metanosulfonil-2-piridazinilo
130
H H H H H 6-metanosulfonil-2-piridazinilo
131
H H H H H 3-piridazinilo
132
H H H H H 2-fluoro-3-piridazinilo
133
H H H H H 5-fluoro-3-piridazinilo
134
H H H H H 6-fluoro-3-piridazinilo
135
H H H H H 2-cloro-3-piridazinilo
136
H H H H H 5-cloro-3-piridazinilo
137
H H H H H 6-cloro-3-piridazinilo
138
H H H H H 2-bromo-3-piridazinilo
139
H H H H H 5-bromo-3-piridazinilo
140
H H H H H 6-bromo-3-piridazinilo
141
H H H H H 2-metoxi-3-piridazinilo
142
H H H H H 5-metoxi-3-piridazinilo
143
H H H H H 6-metoxi-3-piridazinilo
144
H H H H H 2-trifluorometoxi-3-piridazinilo
145
H H H H H 5-trifluorometoxi-3-piridazinilo
146
H H H H H 6-trifluorometoxi-3-piridazinilo
147
H H H H H 2-metil-3-piridazinilo
148
H H H H H 5-metil-3-piridazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
149
H H H H H 6-metil-3-piridazinilo
150
H H H H H 2-trifluorometil-3-piridazinilo
151
H H H H H 5-trifluorometil-3-piridazinilo
152
H H H H H 6-trifluorometil-3-piridazinilo
153
H H H H H 2-ciano-3-piridazinilo
154
H H H H H 5-ciano-3-piridazinilo
155
H H H H H 6-ciano-3-piridazinilo
156
H H H H H 2-nitro-3-piridazinilo
157
H H H H H 5-nitro-3-piridazinilo
158
H H H H H 6-nitro-3-piridazinilo
159
H H H H H 2-metanosulfonil-3-piridazinilo
160
H H H H H 5-metanosulfonil-3-piridazinilo
161
H H H H H 6-metanosulfonil-3-piridazinilo
162
H H H H H 2-pirimidilo
163
H H H H H 4-fluoro-2-pirimidilo
164
H H H H H 5-fluoro-2-pirimidilo
165
H H H H H 4-cloro-2-pirimidilo
166
H H H H H 5-cloro-2-pirimidilo
167
H H H H H 4-bromo-2-pirimidilo
168
H H H H H 5-bromo-2-pirimidilo
169
H H H H H 4-metoxi-2-pirimidilo
170
H H H H H 5-metoxi-2-pirimidilo
171
H H H H H 4-trifluorometoxi-2-pirimidilo
172
H H H H H 5-trifluorometoxi-2-pirimidilo
173
H H H H H 4-metil-2-pirimidilo
174
H H H H H 5-metil-2-pirimidilo
175
H H H H H 4-trifluorometil-2-pirimidilo
176
H H H H H 5-trifluorometil-2-pirimidilo
177
H H H H H 4-ciano-2-pirimidilo
178
H H H H H 5-ciano-2-pirimidilo
179
H H H H H 4-nitro-2-pirimidilo
180
H H H H H 5-nitro-2-pirimidilo
181
H H H H H 4-metanosulfonil-2-pirimidilo
182
H H H H H 5-metanosulfonil-2-pirimidilo
183
H H H H H 4-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
184
H H H H H 2-fluoro-4-pirimidilo
185
H H H H H 5-fluoro-4-pirimidilo
186
H H H H H 6-fluoro-4-pirimidilo
187
H H H H H 2-cloro-4-pirimidilo
188
H H H H H 5-cloro-4-pirimidilo
189
H H H H H 6-cloro-4-pirimidilo
190
H H H H H 2-bromo-4-pirimidilo
191
H H H H H 5-bromo-4-pirimidilo
192
H H H H H 6-bromo-4-pirimidilo
193
H H H H H 2-metoxi-4-pirimidilo
194
H H H H H 5-metoxi-4-pirimidilo
195
H H H H H 6-metoxi-4-pirimidilo
196
H H H H H 2-trifluorometoxi-4-pirimidilo
197
H H H H H 5-trifluorometoxi-4-pirimidilo
198
H H H H H 6-trifluorometoxi-4-pirimidilo
199
H H H H H 2-metil-4-pirimidilo
200
H H H H H 5-metil-4-pirimidilo
201
H H H H H 6-metil-4-pirimidilo
202
H H H H H 2-trifluorometil-4-pirimidilo
203
H H H H H 5-trifluorometil-4-pirimidilo
204
H H H H H 6-trifluorometil-4-pirimidilo
205
H H H H H 2-ciano-4-pirimidilo
206
H H H H H 5-ciano-4-pirimidilo
207
H H H H H 6-ciano-4-pirimidilo
208
H H H H H 2-nitro-4-pirimidilo
209
H H H H H 5-nitro-4-pirimidilo
210
H H H H H 6-nitro-4-pirimidilo
211
H H H H H 2-metanosulfonil-4-pirimidilo
212
H H H H H 5-metanosulfonil-4-pirimidilo
213
H H H H H 6-metanosulfonil-4-pirimidilo
214
H H H H H 5-pirimidilo
215
H H H H H 2-fluoro-5-pirimidilo
216
H H H H H 4-fluoro-5-pirimidilo
217
H H H H H 2-cloro-5-pirimidilo
218
H H H H H 4-cloro-5-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
219
H H H H H 2-bromo-5-pirimidilo
220
H H H H H 4-bromo-5-pirimidilo
221
H H H H H 2-metoxi-5-pirimidilo
222
H H H H H 4-metoxi-5-pirimidilo
223
H H H H H 2-trifluorometoxi-5-pirimidilo
224
H H H H H 4-trifluorometoxi-5-pirimidilo
225
H H H H H 2-metil-5-pirimidilo
226
H H H H H 4-metil-5-pirimidilo
227
H H H H H 2-trifluorometil-5-pirimidilo
228
H H H H H 4-trifluorometil-5-pirimidilo
229
H H H H H 2-ciano-5-pirimidilo
230
H H H H H 4-ciano-5-pirimidilo
231
H H H H H 2-nitro-5-pirimidilo
232
H H H H H 4-nitro-5-pirimidilo
233
H H H H H 2-metanosulfonil-5-pirimidilo
234
H H H H H 4-metanosulfonil-5-pirimidilo
235
H H H H H 2-pirazinilo
236
H H H H H 3-fluoro-2-pirazinilo
237
H H H H H 5-fluoro-2-pirazinilo
238
H H H H H 6-fluoro-2-pirazinilo
239
H H H H H 3-cloro-2-pirazinilo
240
H H H H H 5-cloro-2-pirazinilo
241
H H H H H 6-cloro-2-pirazinilo
242
H H H H H 3-bromo-2-pirazinilo
243
H H H H H 5-bromo-2-pirazinilo
244
H H H H H 6-bromo-2-pirazinilo
245
H H H H H 3-metoxi-2-pirazinilo
246
H H H H H 5-metoxi-2-pirazinilo
247
H H H H H 6-metoxi-2-pirazinilo
248
H H H H H 3-trifluorometoxi-2-pirazinilo
249
H H H H H 5-trifluorometoxi-2-pirazinilo
250
H H H H H 6-trifluorometoxi-2-pirazinilo
251
H H H H H 3-metil-2-pirazinilo
252
H H H H H 5-metil-2-pirazinilo
253
H H H H H 6-metil-2-pirazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
254
H H H H H 3-trifluorometil-2-pirazinilo
255
H H H H H 5-trifluorometil-2-pirazinilo
256
H H H H H 6-trifluorometil-2-pirazinilo
257
H H H H H 3-ciano-2-pirazinilo
258
H H H H H 5-ciano-2-pirazinilo
259
H H H H H 6-ciano-2-pirazinilo
260
H H H H H 3-nitro-2-pirazinilo
261
H H H H H 5-nitro-2-pirazinilo
262
H H H H H 6-nitro-2-pirazinilo
263
H H H H H 3-metilsulfonato-2-pirazinilo
264
H H H H H 5-metilsulfonato-2-pirazinilo
265
H H H H H 6-metilsulfonato-2-pirazinilo
266
H H H H H 2-furanilo
267
H H H H H 3-fluoro-2-furanilo
268
H H H H H 4-fluoro-2-furanilo
269
H H H H H 5-fluoro-2-furanilo
270
H H H H H 3-cloro-2-furanilo
271
H H H H H 4-cloro-2-furanilo
272
H H H H H 5-cloro-2-furanilo
273
H H H H H 3-bromo-2-furanilo
274
H H H H H 4-bromo-2-furanilo
275
H H H H H 5-bromo-2-furanilo
276
H H H H H 3-metoxi-2-furanilo
277
H H H H H 4-metoxi-2-furanilo
278
H H H H H 5-metoxi-2-furanilo
279
H H H H H 3-trifluorometoxi-2-furanilo
280
H H H H H 4-trifluorometoxi-2-furanilo
281
H H H H H 5-trifluorometoxi-2-furanilo
282
H H H H H 3-metil-2-furanilo
283
H H H H H 4-metil-2-furanilo
284
H H H H H 5-metil-2-furanilo
285
H H H H H 3-trifluorometil-2-furanilo
286
H H H H H 4-trifluorometil-2-furanilo
287
H H H H H 5-trifluorometil-2-furanilo
288
H H H H H 3-ciano-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
289
H H H H H 4-ciano-2-furanilo
290
H H H H H 5-ciano-2-furanilo
291
H H H H H 3-nitro-2-furanilo
292
H H H H H 4-nitro-2-furanilo
293
H H H H H 5-nitro-2-furanilo
294
H H H H H 3-metanosulfonil-2-furanilo
295
H H H H H 4-metanosulfonil-2-furanilo
296
H H H H H 5-metanosufonil-2-furanilo
297
H H H H H 3-furanilo
298
H H H H H 3-fluoro-2-furanilo
299
H H H H H 4-fluoro-2-furanilo
300
H H H H H 5-fluoro-2-furanilo
301
H H H H H 3-cloro-2-furanilo
302
H H H H H 4-cloro-2-furanilo
303
H H H H H 5-cloro-2-furanilo
304
H H H H H 3-bromo-2-furanilo
305
H H H H H 4-bromo-2-furanilo
306
H H H H H 5-bromo-2-furanilo
307
H H H H H 3-metoxi-2-furanilo
308
H H H H H 4-metoxi-2-furanilo
309
H H H H H 5-metoxi-2-furanilo
310
H H H H H 3-trifluorometoxi-2-furanilo
311
H H H H H 4-trifluorometoxi-2-furanilo
312
H H H H H 5-trifluorometoxi-2-furanilo
313
H H H H H 3-metil-2-furanilo
314
H H H H H 4-metil-2-furanilo
315
H H H H H 5-metil-2-furanilo
316
H H H H H 3-trifluorometil-2-furanilo
317
H H H H H 4-trifluorometil-2-furanilo
318
H H H H H 5-trifluorometil-2-furanilo
319
H H H H H 3-ciano-2-furanilo
320
H H H H H 4-ciano-2-furanilo
321
H H H H H 5-ciano-2-furanilo
322
H H H H H 3-nitro-2-furanilo
323
H H H H H 4-nitro-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
324
H H H H H 5-nitro-2-furanilo
325
H H H H H 3-metanosulfonil-2-furanilo
326
H H H H H 4-metanosulfonil-2-furanilo
327
H H H H H 5-metanosufonil-2-furanilo
328
H H H H H 3-furanilo
329
H H H H H 2-fluoro-3-furanilo
330
H H H H H 4-fluoro-3-furanilo
331
H H H H H 5-fluoro-3-furanilo
332
H H H H H 2-cloro-3-furanilo
333
H H H H H 4-cloro-3-furanilo
334
H H H H H 5-cloro-3-furanilo
335
H H H H H 2-bromo-3-furanilo
336
H H H H H 4-bromo-3-furanilo
337
H H H H H 5-bromo-3-furanilo
338
H H H H H 2-metoxi-3-furanilo
339
H H H H H 4-metoxi-3-furanilo
340
H H H H H 5-metoxi-3-furanilo
341
H H H H H 2-trifluorometoxi-3-furanilo
342
H H H H H 4-trifluorometoxi-3-furanilo
343
H H H H H 5-trifluorometoxi-3-furanilo
344
H H H H H 2-metil-3-furanilo
345
H H H H H 4-metil-3-furanilo
346
H H H H H 5-metil-3-furanilo
347
H H H H H 2-trifluorometil-3-furanilo
348
H H H H H 4-trifluorometil-3-furanilo
349
H H H H H 5-trifluorometil-3-furanilo
350
H H H H H 2-ciano-3-furanilo
351
H H H H H 4-ciano-3-furanilo
352
H H H H H 5-ciano-3-furanilo
353
H H H H H 2-nitro-3-furanilo
354
H H H H H 4-nitro-3-furanilo
355
H H H H H 5-nitro-3-furanilo
356
H H H H H 2-metanosulfonil-3-furanilo
357
H H H H H 4-metanosulfonil-3-furanilo
358
H H H H H 5-metanosufonil-3-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
359
H H H H H 2-tiofenilo
360
H H H H H 3-fluoro-2-tiofenilo
361
H H H H H 4-fluoro-2-tiofenilo
362
H H H H H 5-fluoro-2-tiofenilo
363
H H H H H 3-cloro-2-tiofenilo
364
H H H H H 4-cloro-2-tiofenilo
365
H H H H H 5-cloro-2-tiofenilo
366
H H H H H 3-bromo-2-tiofenilo
367
H H H H H 4-bromo-2-tiofenilo
368
H H H H H 5-bromo-2-tiofenilo
369
H H H H H 3-metoxi-2-tiofenilo
370
H H H H H 4-metoxi-2-tiofenilo
371
H H H H H 5-metoxi-2-tiofenilo
372
H H H H H 3-trifluorometoxi-2-tiofenilo
373
H H H H H 4-trifluorometoxi-2-tiofenilo
374
H H H H H 5-trifluorometoxi-2-tiofenilo
375
H H H H H 3-metil-2-tiofenilo
376
H H H H H 4-metil-2-tiofenilo
377
H H H H H 5-metil-2-tiofenilo
378
H H H H H 3-trifluorometil-2-tiofenilo
379
H H H H H 4-trifluorometil-2-tiofenilo
380
H H H H H 5-trifluorometil-2-tiofenilo
381
H H H H H 3-ciano-2-tiofenilo
382
H H H H H 4-ciano-2-tiofenilo
383
H H H H H 5-ciano-2-tiofenilo
384
H H H H H 3-nitro-2-tiofenilo
385
H H H H H 4-nitro-2-tiofenilo
386
H H H H H 5-nitro-2-tiofenilo
387
H H H H H 3-metanosulfonil-2-tiofenilo
388
H H H H H 4-metanosulfonil-2-tiofenilo
389
H H H H H 5-metanosufonil-2-tiofenilo
390
H H H H H 3-tiofenilo
391
H H H H H 3-fluoro-2-tiofenilo
392
H H H H H 4-fluoro-2-tiofenilo
393
H H H H H 5-fluoro-2-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
394
H H H H H 3-cloro-2-tiofenilo
395
H H H H H 4-cloro-2-tiofenilo
396
H H H H H 5-cloro-2-tiofenilo
397
H H H H H 3-bromo-2-tiofenilo
398
H H H H H 4-bromo-2-tiofenilo
399
H H H H H 5-bromo-2-tiofenilo
400
H H H H H 3-metoxi-2-tiofenilo
401
H H H H H 4-metoxi-2-tiofenilo
402
H H H H H 5-metoxi-2-tiofenilo
403
H H H H H 3-trifluorometoxi-2-tiofenilo
404
H H H H H 4-trifluorometoxi-2-tiofenilo
405
H H H H H 5-trifluorometoxi-2-tiofenilo
406
H H H H H 3-metil-2-tiofenilo
407
H H H H H 4-metil-2-tiofenilo
408
H H H H H 5-metil-2-tiofenilo
409
H H H H H 3-trifluorometil-2-tiofenilo
410
H H H H H 4-trifluorometil-2-tiofenilo
411
H H H H H 5-trifluorometil-2-tiofenilo
412
H H H H H 3-ciano-2-tiofenilo
413
H H H H H 4-ciano-2-tiofenilo
414
H H H H H 5-ciano-2-tiofenilo
415
H H H H H 3-nitro-2-tiofenilo
416
H H H H H 4-nitro-2-tiofenilo
417
H H H H H 5-nitro-2-tiofenilo
418
H H H H H 3-metanosulfonil-2-tiofenilo
419
H H H H H 4-metanosulfonil-2-tiofenilo
420
H H H H H 5-metanosufonil-2-tiofenilo
421
H H H H H 3-tiofenilo
422
H H H H H 2-fluoro-3-tiofenilo
423
H H H H H 4-fluoro-3-tiofenilo
424
H H H H H 5-fluoro-3-tiofenilo
425
H H H H H 2-cloro-3-tiofenilo
426
H H H H H 4-cloro-3-tiofenilo
427
H H H H H 5-cloro-3-tiofenilo
428
H H H H H 2-bromo-3-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
429
H H H H H 4-bromo-3-tiofenilo
430
H H H H H 5-bromo-3-tiofenilo
431
H H H H H 2-metoxi-3-tiofenilo
432
H H H H H 4-metoxi-3-tiofenilo
433
H H H H H 5-metoxi-3-tiofenilo
434
H H H H H 2-trifluorometoxi-3-tiofenilo
435
H H H H H 4-trifluorometoxi-3-tiofenilo
436
H H H H H 5-trifluorometoxi-3-tiofenilo
437
H H H H H 2-metil-3-tiofenilo
438
H H H H H 4-metil-3-tiofenilo
439
H H H H H 5-metil-3-tiofenilo
440
H H H H H 2-trifluorometil-3-tiofenilo
441
H H H H H 4-trifluorometil-3-tiofenilo
442
H H H H H 5-trifluorometil-3-tiofenilo
443
H H H H H 2-ciano-3-tiofenilo
444
H H H H H 4-ciano-3-tiofenilo
445
H H H H H 5-ciano-3-tiofenilo
446
H H H H H 2-nitro-3-tiofenilo
447
H H H H H 4-nitro-3-tiofenilo
448
H H H H H 5-nitro-3-tiofenilo
449
H H H H H 2-metanosulfonil-3-tiofenilo
450
H H H H H 4-metanosulfonil-3-tiofenilo
451
H H H H H 5-metanosufonil-3-tiofenilo
452
H H H H H 2-ozaxol
453
H H H H H 4-fluoro-2-ozaxol
454
H H H H H 5-fluoro-2-ozaxol
455
H H H H H 4-cloro-2-ozaxol
456
H H H H H 5-cloro-2-ozaxol
457
H H H H H 4-bromo-2-ozaxol
458
H H H H H 5-bromo-2-ozaxol
459
H H H H H 4-metoxi-2-ozaxol
460
H H H H H 5-metoxi-2-ozaxol
461
H H H H H 4-trifluorometoxi-2-ozaxol
462
H H H H H 5-trifluorometoxi-2-ozaxol
463
H H H H H 4-metil-2-ozaxol
Compuesto número
R5 R6 R7 R8 R9 HetAr
464
H H H H H 5-metil-2-ozaxol
465
H H H H H 4-trifluorometil-2-ozaxol
466
H H H H H 5-trifluorometil-2-ozaxol
467
H H H H H 4-ciano-2-ozaxol
468
H H H H H 5-ciano-2-ozaxol
469
H H H H H 4-nitro-2-ozaxol
470
H H H H H 5-nitro-2-ozaxol
471
H H H H H 4-metanosulfonil-2-ozaxol
472
H H H H H 5-metanosulfonil-2-ozaxol
473
H H H H H 4-ozaxol
474
H H H H H 2-fluoro-4-ozaxol
475
H H H H H 5-fluoro-4-ozaxol
476
H H H H H 2-cloro-4-ozaxol
477
H H H H H 5-cloro-4-ozaxol
478
H H H H H 2-bromo-4-ozaxol
479
H H H H H 5-bromo-4-ozaxol
480
H H H H H 2-metoxi-4-ozaxol
481
H H H H H 5-metoxi-4-ozaxol
482
H H H H H 2-trifluorometoxi-4-ozaxol
483
H H H H H 5-trifluorometoxi-4-ozaxol
484
H H H H H 2-metil-4-ozaxol
485
H H H H H 5-metil-4-ozaxol
486
H H H H H 4-trifluorometil-4-ozaxol
487
H H H H H 5-trifluorometil-4-ozaxol
488
H H H H H 4-ciano-4-ozaxol
489
H H H H H 5-ciano-4-ozaxol
490
H H H H H 4-nitro-4-ozaxol
491
H H H H H 5-nitro-4-ozaxol
492
H H H H H 4-metanosulfonil-4-ozaxol
493
H H H H H 5-metanosulfonil-4-ozaxol
494
H H H H H 5-ozaxol
495
H H H H H 2-fluoro-5-ozaxol
496
H H H H H 4-fluoro-5-ozaxol
497
H H H H H 2-cloro-5-ozaxol
498
H H H H H 4-cloro-5-ozaxol
Compuesto número
R5 R6 R7 R8 R9 HetAr
499
H H H H H 2-bromo-5-ozaxol
500
H H H H H 4-bromo-5-ozaxol
501
H H H H H 2-metoxi-5-ozaxol
502
H H H H H 4-metoxi-5-ozaxol
503
H H H H H 2-trifluorometoxi-5-ozaxol
504
H H H H H 4-trifluorometoxi-5-ozaxol
505
H H H H H 2-metil-5-ozaxol
506
H H H H H 4-metil-5-ozaxol
507
H H H H H 2-trifluorometil-5-ozaxol
508
H H H H H 4-trifluorometil-5-ozaxol
509
H H H H H 2-ciano-5-ozaxol
510
H H H H H 4-ciano-5-ozaxol
511
H H H H H 2-nitro-5-ozaxol
512
H H H H H 4-nitro-5-ozaxol
513
H H H H H 2-metanosulfonil-5-ozaxol
514
H H H H H 4-metanosulfonil-5-ozaxol
515
H H H H H 2-tiazol
516
H H H H H 4-fluoro-2-tiazol
517
H H H H H 5-fluoro-2-tiazol
518
H H H H H 4-cloro-2-tiazol
519
H H H H H 5-cloro-2-tiazol
520
H H H H H 4-bromo-2-tiazol
521
H H H H H 5-bromo-2-tiazol
522
H H H H H 4-metoxi-2-tiazol
523
H H H H H 5-metoxi-2-tiazol
524
H H H H H 4-trifluorometoxi-2-tiazol
525
H H H H H 5-trifluorometoxi-2-tiazol
526
H H H H H 4-metil-2-tiazol
527
H H H H H 5-metil-2-tiazol
528
H H H H H 4-trifluorometil-2-tiazol
529
H H H H H 5-trifluorometil-2-tiazol
530
H H H H H 4-ciano-2-tiazol
531
H H H H H 5-ciano-2-tiazol
532
H H H H H 4-nitro-2-tiazol
533
H H H H H 5-nitro-2-tiazol
Compuesto número
R5 R6 R7 R8 R9 HetAr
534
H H H H H 4-metanosulfonil-2-tiazol
535
H H H H H 5-metanosulfonil-2-tiazol
536
H H H H H 4-tiazol
537
H H H H H 2-fluoro-4-tiazol
538
H H H H H 5-fluoro-4-tiazol
539
H H H H H 2-cloro-4-tiazol
540
H H H H H 5-cloro-4-tiazol
541
H H H H H 2-bromo-4-tiazol
542
H H H H H 5-bromo-4-tiazol
543
H H H H H 2-metoxi-4-tiazol
544
H H H H H 5-metoxi-4-tiazol
545
H H H H H 2-trifluorometoxi-4-tiazol
546
H H H H H 5-trifluorometoxi-4-tiazol
547
H H H H H 2-metil-4-tiazol
548
H H H H H 5-metil-4-tiazol
549
H H H H H 4-trifluorometil-4-tiazol
550
H H H H H 5-trifluorometil-4-tiazol
551
H H H H H 4-ciano-4-tiazol
552
H H H H H 5-ciano-4-tiazol
553
H H H H H 4-nitro-4-tiazol
554
H H H H H 5-nitro-4-tiazol
555
H H H H H 4-metanosulfonil-4-tiazol
556
H H H H H 5-metanosulfonil-4-tiazol
557
H H H H H 5-tiazol
558
H H H H H 2-fluoro-5-tiazol
559
H H H H H 4-fluoro-5-tiazol
560
H H H H H 2-cloro-5-tiazol
561
H H H H H 4-cloro-5-tiazol
562
H H H H H 2-bromo-5-tiazol
563
H H H H H 4-bromo-5-tiazol
564
H H H H H 2-metoxi-5-tiazol
565
H H H H H 4-metoxi-5-tiazol
566
H H H H H 2-trifluorometoxi-5-tiazol
567
H H H H H 4-trifluorometoxi-5-tiazol
568
H H H H H 2-metil-5-tiazol
Compuesto número
R5 R6 R7 R8 R9 HetAr
569
H H H H H 4-metil-5-tiazol
570
H H H H H 2-trifluorometil-5-tiazol
571
H H H H H 4-trifluorometil-5-tiazol
572
H H H H H 2-ciano-5-tiazol
573
H H H H H 4-ciano-5-tiazol
574
H H H H H 2-nitro-5-tiazol
575
H H H H H 4-nitro-5-tiazol
576
H H H H H 2-metanosulfonil-5-tiazol
577
H CH3 H H H 4-metanosulfonil-5-tiazol
578
H CH3 H H H 2-piridilo
579
H CH3 H H H 3-fluoro-2-piridilo
580
H CH3 H H H 4-fluoro-2-piridilo
581
H CH3 H H H 5-fluoro-2-piridilo
582
H CH3 H H H 6-fluoro-2-piridilo
583
H CH3 H H H 3-cloro-2-piridilo
584
H CH3 H H H 4-cloro-2-piridilo
585
H CH3 H H H 5-cloro-2-piridilo
586
H CH3 H H H 6-cloro-2-piridilo
587
H CH3 H H H 3-metil-2-piridilo
588
H CH3 H H H 4-metil-2-piridilo
589
H CH3 H H H 5-metil-2-piridilo
590
H CH3 H H H 6-metil-2-piridilo
591
H CH3 H H H 3-trifluorometil-2-piridilo
592
H CH3 H H H 4-trifluorometil-2-piridilo
593
H CH3 H H H 5-trifluorometil-2-piridilo
594
H CH3 H H H 6-trifluorometil-2-piridilo
595
H CH3 H H H 3-metoxi-2-piridilo
596
H CH3 H H H 4-metoxi-2-piridilo
597
H CH3 H H H 5-metoxi-2-piridilo
598
H CH3 H H H 6-metoxi-2-piridilo
599
H CH3 H H H 3-trifluorometoxi-2-piridilo
600
H CH3 H H H 4-trifluorometoxi-2-piridilo
601
H CH3 H H H 5-trifluorometoxi-2-piridilo
602
H CH3 H H H 6-trifluorometoxi-2-piridilo
603
H CH3 H H H 3-ciano-2-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
604
H CH3 H H H 4-ciano-2-piridilo
605
H CH3 H H H 5-ciano-2-piridilo
606
H CH3 H H H 6-ciano-2-piridilo
607
H CH3 H H H 3-nitro-2-piridilo
608
H CH3 H H H 4-nitro-2-piridilo
609
H CH3 H H H 5-nitro-2-piridilo
610
H CH3 H H H 6-nitro-2-piridilo
611
H CH3 H H H 3-metanosulfonil-2-piridilo
612
H CH3 H H H 4-metanosulfonil-2-piridilo
613
H CH3 H H H 5-metanosulfonil-2-piridilo
614
H CH3 H H H 6-metanosulfonil-2-piridilo
615
H CH3 H H H 3-piridilo
616
H CH3 H H H 2-fluoro-3-piridilo
617
H CH3 H H H 4-fluoro-3-piridilo
618
H CH3 H H H 5-fluoro-3-piridilo
619
H CH3 H H H 6-fluoro-3-piridilo
620
H CH3 H H H 2-cloro-3-piridilo
621
H CH3 H H H 4-cloro-3-piridilo
622
H CH3 H H H 5-cloro-3-piridilo
623
H CH3 H H H 6-cloro-3-piridilo
624
H CH3 H H H 2-bromo-3-piridilo
625
H CH3 H H H 4-bromo-3-piridilo
626
H CH3 H H H 5-bromo-3-piridilo
627
H CH3 H H H 6-bromo-3-piridilo
628
H CH3 H H H 2-metoxi-3-piridilo
629
H CH3 H H H 4-metoxi-3-piridilo
630
H CH3 H H H 5-metoxi-3-piridilo
631
H CH3 H H H 6-metoxi-3-piridilo
632
H CH3 H H H 2-trifluorometoxi-3-piridilo
633
H CH3 H H H 4-trifluorometoxi-3-piridilo
634
H CH3 H H H 5-trifluorometoxi-3-piridilo
635
H CH3 H H H 6-trifluorometoxi-3-piridilo
636
H CH3 H H H 2-metil-3-piridilo
637
H CH3 H H H 4-metil-3-piridilo
638
H CH3 H H H 5-metil-3-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
639
H CH3 H H H 6-metil-3-piridilo
640
H CH3 H H H 2-trifluorometil-3-piridilo
641
H CH3 H H H 4-trifluorometil-3-piridilo
642
H CH3 H H H 5-trifluorometil-3-piridilo
643
H CH3 H H H 6-trifluorometil-3-piridilo
644
H CH3 H H H 2-ciano-3-piridilo
645
H CH3 H H H 4-ciano-3-piridilo
646
H CH3 H H H 5-ciano-3-piridilo
647
H CH3 H H H 6-ciano-3-piridilo
648
H CH3 H H H 2-nitro-3-piridilo
649
H CH3 H H H 4-nitro-3-piridilo
650
H CH3 H H H 5-nitro-3-piridilo
651
H CH3 H H H 6-nitro-3-piridilo
652
H CH3 H H H 2-metanosulfonil-3-piridilo
653
H CH3 H H H 4-metanosulfonil-3-piridilo
654
H CH3 H H H 5-metanosulfonil-3-piridilo
655
H CH3 H H H 6-metanosulfonil-3-piridilo
656
H CH3 H H H 4-piridilo
657
H CH3 H H H 2-fluoro-4-piridilo
658
H CH3 H H H 3-fluoro-4-piridilo
659
H CH3 H H H 2-cloro-4-piridilo
660
H CH3 H H H 3-cloro-4-piridilo
661
H CH3 H H H 2-bromo-4-piridilo
662
H CH3 H H H 3-bromo-4-piridilo
663
H CH3 H H H 2-metoxi-4-piridilo
664
H CH3 H H H 3-metoxi-4-piridilo
665
H CH3 H H H 2-trifluorometoxi-4-piridilo
666
H CH3 H H H 3-trifluorometoxi-4-piridilo
667
H CH3 H H H 2-metil-4-piridilo
668
H CH3 H H H 3-metil-4-piridilo
669
H CH3 H H H 2-trifluorometil-4-piridilo
670
H CH3 H H H 3-trifluorometil-4-piridilo
671
H CH3 H H H 2-ciano-4-piridilo
672
H CH3 H H H 3-ciano-4-piridilo
673
H CH3 H H H 2-nitro-4-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
674
H CH3 H H H 3-nitro-4-piridilo
675
H CH3 H H H 2-metanosulfonil-4-piridilo
676
H CH3 H H H 3-metanosulfonil-4-piridilo
677
H CH3 H H H 2-piridazinilo
678
H CH3 H H H 4-fluoro-2-piridazinilo
679
H CH3 H H H 5-fluoro-2-piridazinilo
680
H CH3 H H H 6-fluoro-2-piridazinilo
681
H CH3 H H H 4-cloro-2-piridazinilo
682
H CH3 H H H 5-cloro-2-piridazinilo
683
H CH3 H H H 6-cloro-2-piridazinilo
684
H CH3 H H H 4-bromo-2-piridazinilo
685
H CH3 H H H 5-bromo-2-piridazinilo
686
H CH3 H H H 6-bromo-2-piridazinilo
687
H CH3 H H H 4-metoxi-2-piridazinilo
688
H CH3 H H H 5-metoxi-2-piridazinilo
689
H CH3 H H H 6-metoxi-2-piridazinilo
690
H CH3 H H H 4-trifluorometoxi-2-piridazinilo
691
H CH3 H H H 5-trifluorometoxi-2-piridazinilo
692
H CH3 H H H 6-trifluorometoxi-2-piridazinilo
693
H CH3 H H H 4-metil-2-piridazinilo
694
H CH3 H H H 5-metil-2-piridazinilo
695
H CH3 H H H 6-metil-2-piridazinilo
696
H CH3 H H H 4-trifluorometil-2-piridazinilo
697
H CH3 H H H 5-trifluorometil-2-piridazinilo
698
H CH3 H H H 6-trifluorometil-2-piridazinilo
699
H CH3 H H H 4-ciano-2-piridazinilo
700
H CH3 H H H 5-ciano-2-piridazinilo
701
H CH3 H H H 6-ciano-2-piridazinilo
702
H CH3 H H H 4-nitro-2-piridazinilo
703
H CH3 H H H 5-nitro-2-piridazinilo
704
H CH3 H H H 6-nitro-2-piridazinilo
705
H CH3 H H H 4-metanosulfonil-2-piridazinilo
706
H CH3 H H H 5-metanosulfonil-2-piridazinilo
707
H CH3 H H H 6-metanosulfonil-2-piridazinilo
708
H CH3 H H H 3-piridazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
709
H CH3 H H H 2-fluoro-3-piridazinilo
710
H CH3 H H H 5-fluoro-3-piridazinilo
711
H CH3 H H H 6-fluoro-3-piridazinilo
712
H CH3 H H H 2-cloro-3-piridazinilo
713
H CH3 H H H 5-cloro-3-piridazinilo
714
H CH3 H H H 6-cloro-3-piridazinilo
715
H CH3 H H H 2-bromo-3-piridazinilo
716
H CH3 H H H 5-bromo-3-piridazinilo
717
H CH3 H H H 6-bromo-3-piridazinilo
718
H CH3 H H H 2-metoxi-3-piridazinilo
719
H CH3 H H H 5-metoxi-3-piridazinilo
720
H CH3 H H H 6-metoxi-3-piridazinilo
721
H CH3 H H H 2-trifluorometoxi-3-piridazinilo
722
H CH3 H H H 5-trifluorometoxi-3-piridazinilo
723
H CH3 H H H 6-trifluorometoxi-3-piridazinilo
724
H CH3 H H H 2-metil-3-piridazinilo
725
H CH3 H H H 5-metil-3-piridazinilo
726
H CH3 H H H 6-metil-3-piridazinilo
727
H CH3 H H H 2-trifluorometil-3-piridazinilo
728
H CH3 H H H 5-trifluorometil-3-piridazinilo
729
H CH3 H H H 6-trifluorometil-3-piridazinilo
730
H CH3 H H H 2-ciano-3-piridazinilo
731
H CH3 H H H 5-ciano-3-piridazinilo
732
H CH3 H H H 6-ciano-3-piridazinilo
733
H CH3 H H H 2-nitro-3-piridazinilo
734
H CH3 H H H 5-nitro-3-piridazinilo
735
H CH3 H H H 6-nitro-3-piridazinilo
736
H CH3 H H H 2-metanosulfonil-3-piridazinilo
737
H CH3 H H H 5-metanosulfonil-3-piridazinilo
738
H CH3 H H H 6-metanosulfonil-3-piridazinilo
739
H CH3 H H H 2-pirimidilo
740
H CH3 H H H 4-fluoro-2-pirimidilo
741
H CH3 H H H 5-fluoro-2-pirimidilo
742
H CH3 H H H 4-cloro-2-pirimidilo
743
H CH3 H H H 5-cloro-2-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
744
H CH3 H H H 4-bromo-2-pirimidilo
745
H CH3 H H H 5-bromo-2-pirimidilo
746
H CH3 H H H 4-metoxi-2-pirimidilo
747
H CH3 H H H 5-metoxi-2-pirimidilo
748
H CH3 H H H 4-trifluorometoxi-2-pirimidilo
749
H CH3 H H H 5-trifluorometoxi-2-pirimidilo
750
H CH3 H H H 4-metil-2-pirimidilo
751
H CH3 H H H 5-metil-2-pirimidilo
752
H CH3 H H H 4-trifluorometil-2-pirimidilo
753
H CH3 H H H 5-trifluorometil-2-pirimidilo
754
H CH3 H H H 4-ciano-2-pirimidilo
755
H CH3 H H H 5-ciano-2-pirimidilo
756
H CH3 H H H 4-nitro-2-pirimidilo
757
H CH3 H H H 5-nitro-2-pirimidilo
758
H CH3 H H H 4-metanosulfonil-2-pirimidilo
759
H CH3 H H H 5-metanosulfonil-2-pirimidilo
760
H CH3 H H H 4-pirimidilo
761
H CH3 H H H 2-fluoro-4-pirimidilo
762
H CH3 H H H 5-fluoro-4-pirimidilo
763
H CH3 H H H 6-fluoro-4-pirimidilo
764
H CH3 H H H 2-cloro-4-pirimidilo
765
H CH3 H H H 5-cloro-4-pirimidilo
766
H CH3 H H H 6-cloro-4-pirimidilo
767
H CH3 H H H 2-bromo-4-pirimidilo
768
H CH3 H H H 5-bromo-4-pirimidilo
769
H CH3 H H H 6-bromo-4-pirimidilo
770
H CH3 H H H 2-metoxi-4-pirimidilo
771
H CH3 H H H 5-metoxi-4-pirimidilo
772
H CH3 H H H 6-metoxi-4-pirimidilo
773
H CH3 H H H 2-trifluorometoxi-4-pirimidilo
774
H CH3 H H H 5-trifluorometoxi-4-pirimidilo
775
H CH3 H H H 6-trifluorometoxi-4-pirimidilo
776
H CH3 H H H 2-metil-4-pirimidilo
777
H CH3 H H H 5-metil-4-pirimidilo
778
H CH3 H H H 6-metil-4-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
779
H CH3 H H H 2-trifluorometil-4-pirimidilo
780
H CH3 H H H 5-trifluorometil-4-pirimidilo
781
H CH3 H H H 6-trifluorometil-4-pirimidilo
782
H CH3 H H H 2-ciano-4-pirimidilo
783
H CH3 H H H 5-ciano-4-pirimidilo
784
H CH3 H H H 6-ciano-4-pirimidilo
785
H CH3 H H H 2-nitro-4-pirimidilo
786
H CH3 H H H 5-nitro-4-pirimidilo
787
H CH3 H H H 6-nitro-4-pirimidilo
788
H CH3 H H H 2-metanosulfonil-4-pirimidilo
789
H CH3 H H H 5-metanosulfonil-4-pirimidilo
790
H CH3 H H H 6-metanosulfonil-4-pirimidilo
791
H CH3 H H H 5-pirimidilo
792
H CH3 H H H 2-fluoro-5-pirimidilo
793
H CH3 H H H 4-fluoro-5-pirimidilo
794
H CH3 H H H 2-cloro-5-pirimidilo
795
H CH3 H H H 4-cloro-5-pirimidilo
796
H CH3 H H H 2-bromo-5-pirimidilo
797
H CH3 H H H 4-bromo-5-pirimidilo
798
H CH3 H H H 2-metoxi-5-pirimidilo
799
H CH3 H H H 4-metoxi-5-pirimidilo
800
H CH3 H H H 2-trifluorometoxi-5-pirimidilo
801
H CH3 H H H 4-trifluorometoxi-5-pirimidilo
802
H CH3 H H H 2-metil-5-pirimidilo
803
H CH3 H H H 4-metil-5-pirimidilo
804
H CH3 H H H 2-trifluorometil-5-pirimidilo
805
H CH3 H H H 4-trifluorometil-5-pirimidilo
806
H CH3 H H H 2-ciano-5-pirimidilo
807
H CH3 H H H 4-ciano-5-pirimidilo
808
H CH3 H H H 2-nitro-5-pirimidilo
809
H CH3 H H H 4-nitro-5-pirimidilo
810
H CH3 H H H 2-metanosulfonil-5-pirimidilo
811
H CH3 H H H 4-metanosulfonil-5-pirimidilo
812
H CH3 H H H 2-pirazinilo
813
H CH3 H H H 3-fluoro-2-pirazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
814
H CH3 H H H 5-fluoro-2-pirazinilo
815
H CH3 H H H 6-fluoro-2-pirazinilo
816
H CH3 H H H 3-cloro-2-pirazinilo
817
H CH3 H H H 5-cloro-2-pirazinilo
818
H CH3 H H H 6-cloro-2-pirazinilo
819
H CH3 H H H 3-bromo-2-pirazinilo
820
H CH3 H H H 5-bromo-2-pirazinilo
821
H CH3 H H H 6-bromo-2-pirazinilo
822
H CH3 H H H 3-metoxi-2-pirazinilo
823
H CH3 H H H 5-metoxi-2-pirazinilo
824
H CH3 H H H 6-metoxi-2-pirazinilo
825
H CH3 H H H 3-trifluorometoxi-2-pirazinilo
826
H CH3 H H H 5-trifluorometoxi-2-pirazinilo
827
H CH3 H H H 6-trifluorometoxi-2-pirazinilo
828
H CH3 H H H 3-metil-2-pirazinilo
829
H CH3 H H H 5-metil-2-pirazinilo
830
H CH3 H H H 6-metil-2-pirazinilo
831
H CH3 H H H 3-trifluorometil-2-pirazinilo
832
H CH3 H H H 5-trifluorometil-2-pirazinilo
833
H CH3 H H H 6-trifluorometil-2-pirazinilo
834
H CH3 H H H 3-ciano-2-pirazinilo
835
H CH3 H H H 5-ciano-2-pirazinilo
836
H CH3 H H H 6-ciano-2-pirazinilo
837
H CH3 H H H 3-nitro-2-pirazinilo
838
H CH3 H H H 5-nitro-2-pirazinilo
839
H CH3 H H H 6-nitro-2-pirazinilo
840
H CH3 H H H 3-metilsulfonato-2-pirazinilo
841
H CH3 H H H 5-metilsulfonato-2-pirazinilo
842
H CH3 H H H 6-metilsulfonato-2-pirazinilo
843
H CH3 H H H 2-furanilo
844
H CH3 H H H 3-fluoro-2-furanilo
845
H CH3 H H H 4-fluoro-2-furanilo
846
H CH3 H H H 5-fluoro-2-furanilo
847
H CH3 H H H 3-cloro-2-furanilo
848
H CH3 H H H 4-cloro-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
849
H CH3 H H H 5-cloro-2-furanilo
850
H CH3 H H H 3-bromo-2-furanilo
851
H CH3 H H H 4-bromo-2-furanilo
852
H CH3 H H H 5-bromo-2-furanilo
853
H CH3 H H H 3-metoxi-2-furanilo
854
H CH3 H H H 4-metoxi-2-furanilo
855
H CH3 H H H 5-metoxi-2-furanilo
856
H CH3 H H H 3-trifluorometoxi-2-furanilo
857
H CH3 H H H 4-trifluorometoxi-2-furanilo
858
H CH3 H H H 5-trifluorometoxi-2-furanilo
859
H CH3 H H H 3-metil-2-furanilo
860
H CH3 H H H 4-metil-2-furanilo
861
H CH3 H H H 5-metil-2-furanilo
862
H CH3 H H H 3-trifluorometil-2-furanilo
863
H CH3 H H H 4-trifluorometil-2-furanilo
864
H CH3 H H H 5-trifluorometil-2-furanilo
865
H CH3 H H H 3-ciano-2-furanilo
866
H CH3 H H H 4-ciano-2-furanilo
867
H CH3 H H H 5-ciano-2-furanilo
868
H CH3 H H H 3-nitro-2-furanilo
869
H CH3 H H H 4-nitro-2-furanilo
870
H CH3 H H H 5-nitro-2-furanilo
871
H CH3 H H H 3-metanosulfonil-2-furanilo
872
H CH3 H H H 4-metanosulfonil-2-furanilo
873
H CH3 H H H 5-metanosufonil-2-furanilo
874
H CH3 H H H 3-furanilo
875
H CH3 H H H 3-fluoro-2-furanilo
876
H CH3 H H H 4-fluoro-2-furanilo
877
H CH3 H H H 5-fluoro-2-furanilo
878
H CH3 H H H 3-cloro-2-furanilo
879
H CH3 H H H 4-cloro-2-furanilo
880
H CH3 H H H 5-cloro-2-furanilo
881
H CH3 H H H 3-bromo-2-furanilo
882
H CH3 H H H 4-bromo-2-furanilo
883
H CH3 H H H 5-bromo-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
884
H CH3 H H H 3-metoxi-2-furanilo
885
H CH3 H H H 4-metoxi-2-furanilo
886
H CH3 H H H 5-metoxi-2-furanilo
887
H CH3 H H H 3-trifluorometoxi-2-furanilo
888
H CH3 H H H 4-trifluorometoxi-2-furanilo
889
H CH3 H H H 5-trifluorometoxi-2-furanilo
890
H CH3 H H H 3-metil-2-furanilo
891
H CH3 H H H 4-metil-2-furanilo
892
H CH3 H H H 5-metil-2-furanilo
893
H CH3 H H H 3-trifluorometil-2-furanilo
894
H CH3 H H H 4-trifluorometil-2-furanilo
895
H CH3 H H H 5-trifluorometil-2-furanilo
896
H CH3 H H H 3-ciano-2-furanilo
897
H CH3 H H H 4-ciano-2-furanilo
898
H CH3 H H H 5-ciano-2-furanilo
899
H CH3 H H H 3-nitro-2-furanilo
900
H CH3 H H H 4-nitro-2-furanilo
901
H CH3 H H H 5-nitro-2-furanilo
902
H CH3 H H H 3-metanosulfonil-2-furanilo
903
H CH3 H H H 4-metanosulfonil-2-furanilo
904
H CH3 H H H 5-metanosufonil-2-furanilo
905
H CH3 H H H 3-furanilo
906
H CH3 H H H 2-fluoro-3-furanilo
907
H CH3 H H H 4-fluoro-3-furanilo
908
H CH3 H H H 5-fluoro-3-furanilo
909
H CH3 H H H 2-cloro-3-furanilo
910
H CH3 H H H 4-cloro-3-furanilo
911
H CH3 H H H 5-cloro-3-furanilo
912
H CH3 H H H 2-bromo-3-furanilo
913
H CH3 H H H 4-bromo-3-furanilo
914
H CH3 H H H 5-bromo-3-furanilo
915
H CH3 H H H 2-metoxi-3-furanilo
916
H CH3 H H H 4-metoxi-3-furanilo
917
H CH3 H H H 5-metoxi-3-furanilo
918
H CH3 H H H 2-trifluorometoxi-3-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
919
H CH3 H H H 4-trifluorometoxi-3-furanilo
920
H CH3 H H H 5-trifluorometoxi-3-furanilo
921
H CH3 H H H 2-metil-3-furanilo
922
H CH3 H H H 4-metil-3-furanilo
923
H CH3 H H H 5-metil-3-furanilo
924
H CH3 H H H 2-trifluorometil-3-furanilo
925
H CH3 H H H 4-trifluorometil-3-furanilo
926
H CH3 H H H 5-trifluorometil-3-furanilo
927
H CH3 H H H 2-ciano-3-furanilo
928
H CH3 H H H 4-ciano-3-furanilo
929
H CH3 H H H 5-ciano-3-furanilo
930
H CH3 H H H 2-nitro-3-furanilo
931
H CH3 H H H 4-nitro-3-furanilo
932
H CH3 H H H 5-nitro-3-furanilo
933
H CH3 H H H 2-metanosulfonil-3-furanilo
934
H CH3 H H H 4-metanosulfonil-3-furanilo
935
H CH3 H H H 5-metanosufonil-3-furanilo
936
H CH3 H H H 2-tiofenilo
937
H CH3 H H H 3-fluoro-2-tiofenilo
938
H CH3 H H H 4-fluoro-2-tiofenilo
939
H CH3 H H H 5-fluoro-2-tiofenilo
940
H CH3 H H H 3-cloro-2-tiofenilo
941
H CH3 H H H 4-cloro-2-tiofenilo
942
H CH3 H H H 5-cloro-2-tiofenilo
943
H CH3 H H H 3-bromo-2-tiofenilo
944
H CH3 H H H 4-bromo-2-tiofenilo
945
H CH3 H H H 5-bromo-2-tiofenilo
946
H CH3 H H H 3-metoxi-2-tiofenilo
947
H CH3 H H H 4-metoxi-2-tiofenilo
948
H CH3 H H H 5-metoxi-2-tiofenilo
949
H CH3 H H H 3-trifluorometoxi-2-tiofenilo
950
H CH3 H H H 4-trifluorometoxi-2-tiofenilo
951
H CH3 H H H 5-trifluorometoxi-2-tiofenilo
952
H CH3 H H H 3-metil-2-tiofenilo
953
H CH3 H H H 4-metil-2-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
954
H CH3 H H H 5-metil-2-tiofenilo
955
H CH3 H H H 3-trifluorometil-2-tiofenilo
956
H CH3 H H H 4-trifluorometil-2-tiofenilo
957
H CH3 H H H 5-trifluorometil-2-tiofenilo
958
H CH3 H H H 3-ciano-2-tiofenilo
959
H CH3 H H H 4-ciano-2-tiofenilo
960
H CH3 H H H 5-ciano-2-tiofenilo
961
H CH3 H H H 3-nitro-2-tiofenilo
962
H CH3 H H H 4-nitro-2-tiofenilo
963
H CH3 H H H 5-nitro-2-tiofenilo
964
H CH3 H H H 3-metanosulfonil-2-tiofenilo
965
H CH3 H H H 4-metanosulfonil-2-tiofenilo
966
H CH3 H H H 5-metanosufonil-2-tiofenilo
967
H CH3 H H H 3-tiofenilo
968
H CH3 H H H 3-fluoro-2-tiofenilo
969
H CH3 H H H 4-fluoro-2-tiofenilo
970
H CH3 H H H 5-fluoro-2-tiofenilo
971
H CH3 H H H 3-cloro-2-tiofenilo
972
H CH3 H H H 4-cloro-2-tiofenilo
973
H CH3 H H H 5-cloro-2-tiofenilo
974
H CH3 H H H 3-bromo-2-tiofenilo
975
H CH3 H H H 4-bromo-2-tiofenilo
976
H CH3 H H H 5-bromo-2-tiofenilo
977
H CH3 H H H 3-metoxi-2-tiofenilo
978
H CH3 H H H 4-metoxi-2-tiofenilo
979
H CH3 H H H 5-metoxi-2-tiofenilo
980
H CH3 H H H 3-trifluorometoxi-2-tiofenilo
981
H CH3 H H H 4-trifluorometoxi-2-tiofenilo
982
H CH3 H H H 5-trifluorometoxi-2-tiofenilo
983
H CH3 H H H 3-metil-2-tiofenilo
984
H CH3 H H H 4-metil-2-tiofenilo
985
H CH3 H H H 5-metil-2-tiofenilo
986
H CH3 H H H 3-trifluorometil-2-tiofenilo
987
H CH3 H H H 4-trifluorometil-2-tiofenilo
988
H CH3 H H H 5-trifluorometil-2-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
989
H CH3 H H H 3-ciano-2-tiofenilo
990
H CH3 H H H 4-ciano-2-tiofenilo
991
H CH3 H H H 5-ciano-2-tiofenilo
992
H CH3 H H H 3-nitro-2-tiofenilo
993
H CH3 H H H 4-nitro-2-tiofenilo
994
H CH3 H H H 5-nitro-2-tiofenilo
995
H CH3 H H H 3-metanosulfonil-2-tiofenilo
996
H CH3 H H H 4-metanosulfonil-2-tiofenilo
997
H CH3 H H H 5-metanosufonil-2-tiofenilo
998
H CH3 H H H 3-tiofenilo
999
H CH3 H H H 2-fluoro-3-tiofenilo
1000
H CH3 H H H 4-fluoro-3-tiofenilo
1001
H CH3 H H H 5-fluoro-3-tiofenilo
1002
H CH3 H H H 2-cloro-3-tiofenilo
1003
H CH3 H H H 4-cloro-3-tiofenilo
1004
H CH3 H H H 5-cloro-3-tiofenilo
1005
H CH3 H H H 2-bromo-3-tiofenilo
1006
H CH3 H H H 4-bromo-3-tiofenilo
1007
H CH3 H H H 5-bromo-3-tiofenilo
1008
H CH3 H H H 2-metoxi-3-tiofenilo
1009
H CH3 H H H 4-metoxi-3-tiofenilo
1010
H CH3 H H H 5-metoxi-3-tiofenilo
1011
H CH3 H H H 2-trifluorometoxi-3-tiofenilo
1012
H CH3 H H H 4-trifluorometoxi-3-tiofenilo
1013
H CH3 H H H 5-trifluorometoxi-3-tiofenilo
1014
H CH3 H H H 2-metil-3-tiofenilo
1015
H CH3 H H H 4-metil-3-tiofenilo
1016
H CH3 H H H 5-metil-3-tiofenilo
1017
H CH3 H H H 2-trifluorometil-3-tiofenilo
1018
H CH3 H H H 4-trifluorometil-3-tiofenilo
1019
H CH3 H H H 5-trifluorometil-3-tiofenilo
1020
H CH3 H H H 2-ciano-3-tiofenilo
1021
H CH3 H H H 4-ciano-3-tiofenilo
1022
H CH3 H H H 5-ciano-3-tiofenilo
1023
H CH3 H H H 2-nitro-3-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1024
H CH3 H H H 4-nitro-3-tiofenilo
1025
H CH3 H H H 5-nitro-3-tiofenilo
1026
H CH3 H H H 2-metanosulfonil-3-tiofenilo
1027
H CH3 H H H 4-metanosulfonil-3-tiofenilo
1028
H CH3 H H H 5-metanosufonil-3-tiofenilo
1029
H CH3 H H H 2-ozaxol
1030
H CH3 H H H 4-fluoro-2-ozaxol
1031
H CH3 H H H 5-fluoro-2-ozaxol
1032
H CH3 H H H 4-cloro-2-ozaxol
1033
H CH3 H H H 5-cloro-2-ozaxol
1034
H CH3 H H H 4-bromo-2-ozaxol
1035
H CH3 H H H 5-bromo-2-ozaxol
1036
H CH3 H H H 4-metoxi-2-ozaxol
1037
H CH3 H H H 5-metoxi-2-ozaxol
1038
H CH3 H H H 4-trifluorometoxi-2-ozaxol
1039
H CH3 H H H 5-trifluorometoxi-2-ozaxol
1040
H CH3 H H H 4-metil-2-ozaxol
1041
H CH3 H H H 5-metil-2-ozaxol
1042
H CH3 H H H 4-trifluorometil-2-ozaxol
1043
H CH3 H H H 5-trifluorometil-2-ozaxol
1044
H CH3 H H H 4-ciano-2-ozaxol
1045
H CH3 H H H 5-ciano-2-ozaxol
1046
H CH3 H H H 4-nitro-2-ozaxol
1047
H CH3 H H H 5-nitro-2-ozaxol
1048
H CH3 H H H 4-metanosulfonil-2-ozaxol
1049
H CH3 H H H 5-metanosulfonil-2-ozaxol
1050
H CH3 H H H 4-ozaxol
1051
H CH3 H H H 2-fluoro-4-ozaxol
1052
H CH3 H H H 5-fluoro-4-ozaxol
1053
H CH3 H H H 2-cloro-4-ozaxol
1054
H CH3 H H H 5-cloro-4-ozaxol
1055
H CH3 H H H 2-bromo-4-ozaxol
1056
H CH3 H H H 5-bromo-4-ozaxol
1057
H CH3 H H H 2-metoxi-4-ozaxol
1058
H CH3 H H H 5-metoxi-4-ozaxol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1059
H CH3 H H H 2-trifluorometoxi-4-ozaxol
1060
H CH3 H H H 5-trifluorometoxi-4-ozaxol
1061
H CH3 H H H 2-metil-4-ozaxol
1062
H CH3 H H H 5-metil-4-ozaxol
1063
H CH3 H H H 4-trifluorometil-4-ozaxol
1064
H CH3 H H H 5-trifluorometil-4-ozaxol
1065
H CH3 H H H 4-ciano-4-ozaxol
1066
H CH3 H H H 5-ciano-4-ozaxol
1067
H CH3 H H H 4-nitro-4-ozaxol
1068
H CH3 H H H 5-nitro-4-ozaxol
1069
H CH3 H H H 4-metanosulfonil-4-ozaxol
1070
H CH3 H H H 5-metanosulfonil-4-ozaxol
1071
H CH3 H H H 5-ozaxol
1072
H CH3 H H H 2-fluoro-5-ozaxol
1073
H CH3 H H H 4-fluoro-5-ozaxol
1074
H CH3 H H H 2-cloro-5-ozaxol
1075
H CH3 H H H 4-cloro-5-ozaxol
1076
H CH3 H H H 2-bromo-5-ozaxol
1077
H CH3 H H H 4-bromo-5-ozaxol
1078
H CH3 H H H 2-metoxi-5-ozaxol
1079
H CH3 H H H 4-metoxi-5-ozaxol
1080
H CH3 H H H 2-trifluorometoxi-5-ozaxol
1081
H CH3 H H H 4-trifluorometoxi-5-ozaxol
1082
H CH3 H H H 2-metil-5-ozaxol
1083
H CH3 H H H 4-metil-5-ozaxol
1084
H CH3 H H H 2-trifluorometil-5-ozaxol
1085
H CH3 H H H 4-trifluorometil-5-ozaxol
1086
H CH3 H H H 2-ciano-5-ozaxol
1087
H CH3 H H H 4-ciano-5-ozaxol
1088
H CH3 H H H 2-nitro-5-ozaxol
1089
H CH3 H H H 4-nitro-5-ozaxol
1090
H CH3 H H H 2-metanosulfonil-5-ozaxol
1091
H CH3 H H H 4-metanosulfonil-5-ozaxol
1092
H CH3 H H H 2-tiazol
1093
H CH3 H H H 4-fluoro-2-tiazol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1094
H CH3 H H H 5-fluoro-2-tiazol
1095
H CH3 H H H 4-cloro-2-tiazol
1096
H CH3 H H H 5-cloro-2-tiazol
1097
H CH3 H H H 4-bromo-2-tiazol
1098
H CH3 H H H 5-bromo-2-tiazol
1099
H CH3 H H H 4-metoxi-2-tiazol
1100
H CH3 H H H 5-metoxi-2-tiazol
1101
H CH3 H H H 4-trifluorometoxi-2-tiazol
1102
H CH3 H H H 5-trifluorometoxi-2-tiazol
1103
H CH3 H H H 4-metil-2-tiazol
1104
H CH3 H H H 5-metil-2-tiazol
1105
H CH3 H H H 4-trifluorometil-2-tiazol
1106
H CH3 H H H 5-trifluorometil-2-tiazol
1107
H CH3 H H H 4-ciano-2-tiazol
1108
H CH3 H H H 5-ciano-2-tiazol
1109
H CH3 H H H 4-nitro-2-tiazol
1110
H CH3 H H H 5-nitro-2-tiazol
1111
H CH3 H H H 4-metanosulfonil-2-tiazol
1112
H CH3 H H H 5-metanosulfonil-2-tiazol
1113
H CH3 H H H 4-tiazol
1114
H CH3 H H H 2-fluoro-4-tiazol
1115
H CH3 H H H 5-fluoro-4-tiazol
1116
H CH3 H H H 2-cloro-4-tiazol
1117
H CH3 H H H 5-cloro-4-tiazol
1118
H CH3 H H H 2-bromo-4-tiazol
1119
H CH3 H H H 5-bromo-4-tiazol
1120
H CH3 H H H 2-metoxi-4-tiazol
1121
H CH3 H H H 5-metoxi-4-tiazol
1122
H CH3 H H H 2-trifluorometoxi-4-tiazol
1123
H CH3 H H H 5-trifluorometoxi-4-tiazol
1124
H CH3 H H H 2-metil-4-tiazol
1125
H CH3 H H H 5-metil-4-tiazol
1126
H CH3 H H H 4-trifluorometil-4-tiazol
1127
H CH3 H H H 5-trifluorometil-4-tiazol
1128
H CH3 H H H 4-ciano-4-tiazol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1129
H CH3 H H H 5-ciano-4-tiazol
1130
H CH3 H H H 4-nitro-4-tiazol
1131
H CH3 H H H 5-nitro-4-tiazol
1132
H CH3 H H H 4-metanosulfonil-4-tiazol
1133
H CH3 H H H 5-metanosulfonil-4-tiazol
1134
H CH3 H H H 5-tiazol
1135
H CH3 H H H 2-fluoro-5-tiazol
1136
H CH3 H H H 4-fluoro-5-tiazol
1137
H CH3 H H H 2-cloro-5-tiazol
1138
H CH3 H H H 4-cloro-5-tiazol
1139
H CH3 H H H 2-bromo-5-tiazol
1140
H CH3 H H H 4-bromo-5-tiazol
1141
H CH3 H H H 2-metoxi-5-tiazol
1142
H CH3 H H H 4-metoxi-5-tiazol
1143
H CH3 H H H 2-trifluorometoxi-5-tiazol
1144
H CH3 H H H 4-trifluorometoxi-5-tiazol
1145
H CH3 H H H 2-metil-5-tiazol
1146
H CH3 H H H 4-metil-5-tiazol
1147
H CH3 H H H 2-trifluorometil-5-tiazol
1148
H CH3 H H H 4-trifluorometil-5-tiazol
1149
H CH3 H H H 2-ciano-5-tiazol
1150
H CH3 H H H 4-ciano-5-tiazol
1151
H CH3 H H H 2-nitro-5-tiazol
1152
H CH3 H H H 4-nitro-5-tiazol
1153
H CH3 H H H 2-metanosulfonil-5-tiazol
1154
H CH3 CH3 H H 4-metanosulfonil-5-tiazol
1155
H CH3 CH3 H H 2-piridilo
1156
H CH3 CH3 H H 3-fluoro-2-piridilo
1157
H CH3 CH3 H H 4-fluoro-2-piridilo
1158
H CH3 CH3 H H 5-fluoro-2-piridilo
1159
H CH3 CH3 H H 6-fluoro-2-piridilo
1160
H CH3 CH3 H H 3-cloro-2-piridilo
1161
H CH3 CH3 H H 4-cloro-2-piridilo
1162
H CH3 CH3 H H 5-cloro-2-piridilo
1163
H CH3 CH3 H H 6-cloro-2-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1164
H CH3 CH3 H H 3-metil-2-piridilo
1165
H CH3 CH3 H H 4-metil-2-piridilo
1166
H CH3 CH3 H H 5-metil-2-piridilo
1167
H CH3 CH3 H H 6-metil-2-piridilo
1168
H CH3 CH3 H H 3-trifluorometil-2-piridilo
1169
H CH3 CH3 H H 4-trifluorometil-2-piridilo
1170
H CH3 CH3 H H 5-trifluorometil-2-piridilo
1171
H CH3 CH3 H H 6-trifluorometil-2-piridilo
1172
H CH3 CH3 H H 3-metoxi-2-piridilo
1173
H CH3 CH3 H H 4-metoxi-2-piridilo
1174
H CH3 CH3 H H 5-metoxi-2-piridilo
1175
H CH3 CH3 H H 6-metoxi-2-piridilo
1176
H CH3 CH3 H H 3-trifluorometoxi-2-piridilo
1177
H CH3 CH3 H H 4-trifluorometoxi-2-piridilo
1178
H CH3 CH3 H H 5-trifluorometoxi-2-piridilo
1179
H CH3 CH3 H H 6-trifluorometoxi-2-piridilo
1180
H CH3 CH3 H H 3-ciano-2-piridilo
1181
H CH3 CH3 H H 4-ciano-2-piridilo
1182
H CH3 CH3 H H 5-ciano-2-piridilo
1183
H CH3 CH3 H H 6-ciano-2-piridilo
1184
H CH3 CH3 H H 3-nitro-2-piridilo
1185
H CH3 CH3 H H 4-nitro-2-piridilo
1186
H CH3 CH3 H H 5-nitro-2-piridilo
1187
H CH3 CH3 H H 6-nitro-2-piridilo
1188
H CH3 CH3 H H 3-metanosulfonil-2-piridilo
1189
H CH3 CH3 H H 4-metanosulfonil-2-piridilo
1190
H CH3 CH3 H H 5-metanosulfonil-2-piridilo
1191
H CH3 CH3 H H 6-metanosulfonil-2-piridilo
1192
H CH3 CH3 H H 3-piridilo
1193
H CH3 CH3 H H 2-fluoro-3-piridilo
1194
H CH3 CH3 H H 4-fluoro-3-piridilo
1195
H CH3 CH3 H H 5-fluoro-3-piridilo
1196
H CH3 CH3 H H 6-fluoro-3-piridilo
1197
H CH3 CH3 H H 2-cloro-3-piridilo
1198
H CH3 CH3 H H 4-cloro-3-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1199
H CH3 CH3 H H 5-cloro-3-piridilo
1200
H CH3 CH3 H H 6-cloro-3-piridilo
1201
H CH3 CH3 H H 2-bromo-3-piridilo
1202
H CH3 CH3 H H 4-bromo-3-piridilo
1203
H CH3 CH3 H H 5-bromo-3-piridilo
1204
H CH3 CH3 H H 6-bromo-3-piridilo
1205
H CH3 CH3 H H 2-metoxi-3-piridilo
1206
H CH3 CH3 H H 4-metoxi-3-piridilo
1207
H CH3 CH3 H H 5-metoxi-3-piridilo
1208
H CH3 CH3 H H 6-metoxi-3-piridilo
1209
H CH3 CH3 H H 2-trifluorometoxi-3-piridilo
1210
H CH3 CH3 H H 4-trifluorometoxi-3-piridilo
1211
H CH3 CH3 H H 5-trifluorometoxi-3-piridilo
1212
H CH3 CH3 H H 6-trifluorometoxi-3-piridilo
1213
H CH3 CH3 H H 2-metil-3-piridilo
1214
H CH3 CH3 H H 4-metil-3-piridilo
1215
H CH3 CH3 H H 5-metil-3-piridilo
1216
H CH3 CH3 H H 6-metil-3-piridilo
1217
H CH3 CH3 H H 2-trifluorometil-3-piridilo
1218
H CH3 CH3 H H 4-trifluorometil-3-piridilo
1219
H CH3 CH3 H H 5-trifluorometil-3-piridilo
1220
H CH3 CH3 H H 6-trifluorometil-3-piridilo
1221
H CH3 CH3 H H 2-ciano-3-piridilo
1222
H CH3 CH3 H H 4-ciano-3-piridilo
1223
H CH3 CH3 H H 5-ciano-3-piridilo
1224
H CH3 CH3 H H 6-ciano-3-piridilo
1225
H CH3 CH3 H H 2-nitro-3-piridilo
1226
H CH3 CH3 H H 4-nitro-3-piridilo
1227
H CH3 CH3 H H 5-nitro-3-piridilo
1228
H CH3 CH3 H H 6-nitro-3-piridilo
1229
H CH3 CH3 H H 2-metanosulfonil-3-piridilo
1230
H CH3 CH3 H H 4-metanosulfonil-3-piridilo
1231
H CH3 CH3 H H 5-metanosulfonil-3-piridilo
1232
H CH3 CH3 H H 6-metanosulfonil-3-piridilo
1233
H CH3 CH3 H H 4-piridilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1234
H CH3 CH3 H H 2-fluoro-4-piridilo
1235
H CH3 CH3 H H 3-fluoro-4-piridilo
1236
H CH3 CH3 H H 2-cloro-4-piridilo
1237
H CH3 CH3 H H 3-cloro-4-piridilo
1238
H CH3 CH3 H H 2-bromo-4-piridilo
1239
H CH3 CH3 H H 3-bromo-4-piridilo
1240
H CH3 CH3 H H 2-metoxi-4-piridilo
1241
H CH3 CH3 H H 3-metoxi-4-piridilo
1242
H CH3 CH3 H H 2-trifluorometoxi-4-piridilo
1243
H CH3 CH3 H H 3-trifluorometoxi-4-piridilo
1244
H CH3 CH3 H H 2-metil-4-piridilo
1245
H CH3 CH3 H H 3-metil-4-piridilo
1246
H CH3 CH3 H H 2-trifluorometil-4-piridilo
1247
H CH3 CH3 H H 3-trifluorometil-4-piridilo
1248
H CH3 CH3 H H 2-ciano-4-piridilo
1249
H CH3 CH3 H H 3-ciano-4-piridilo
1250
H CH3 CH3 H H 2-nitro-4-piridilo
1251
H CH3 CH3 H H 3-nitro-4-piridilo
1252
H CH3 CH3 H H 2-metanosulfonil-4-piridilo
1253
H CH3 CH3 H H 3-metanosulfonil-4-piridilo
1254
H CH3 CH3 H H 2-piridazinilo
1255
H CH3 CH3 H H 4-fluoro-2-piridazinilo
1256
H CH3 CH3 H H 5-fluoro-2-piridazinilo
1257
H CH3 CH3 H H 6-fluoro-2-piridazinilo
1258
H CH3 CH3 H H 4-cloro-2-piridazinilo
1259
H CH3 CH3 H H 5-cloro-2-piridazinilo
1260
H CH3 CH3 H H 6-cloro-2-piridazinilo
1261
H CH3 CH3 H H 4-bromo-2-piridazinilo
1262
H CH3 CH3 H H 5-bromo-2-piridazinilo
1263
H CH3 CH3 H H 6-bromo-2-piridazinilo
1264
H CH3 CH3 H H 4-metoxi-2-piridazinilo
1265
H CH3 CH3 H H 5-metoxi-2-piridazinilo
1266
H CH3 CH3 H H 6-metoxi-2-piridazinilo
1267
H CH3 CH3 H H 4-trifluorometoxi-2-piridazinilo
1268
H CH3 CH3 H H 5-trifluorometoxi-2-piridazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1269
H CH3 CH3 H H 6-trifluorometoxi-2-piridazinilo
1270
H CH3 CH3 H H 4-metil-2-piridazinilo
1271
H CH3 CH3 H H 5-metil-2-piridazinilo
1272
H CH3 CH3 H H 6-metil-2-piridazinilo
1273
H CH3 CH3 H H 4-trifluorometil-2-piridazinilo
1274
H CH3 CH3 H H 5-trifluorometil-2-piridazinilo
1275
H CH3 CH3 H H 6-trifluorometil-2-piridazinilo
1276
H CH3 CH3 H H 4-ciano-2-piridazinilo
1277
H CH3 CH3 H H 5-ciano-2-piridazinilo
1278
H CH3 CH3 H H 6-ciano-2-piridazinilo
1279
H CH3 CH3 H H 4-nitro-2-piridazinilo
1280
H CH3 CH3 H H 5-nitro-2-piridazinilo
1281
H CH3 CH3 H H 6-nitro-2-piridazinilo
1282
H CH3 CH3 H H 4-metanosulfonil-2-piridazinilo
1283
H CH3 CH3 H H 5-metanosulfonil-2-piridazinilo
1284
H CH3 CH3 H H 6-metanosulfonil-2-piridazinilo
1285
H CH3 CH3 H H 3-piridazinilo
1286
H CH3 CH3 H H 2-fluoro-3-piridazinilo
1287
H CH3 CH3 H H 5-fluoro-3-piridazinilo
1288
H CH3 CH3 H H 6-fluoro-3-piridazinilo
1289
H CH3 CH3 H H 2-cloro-3-piridazinilo
1290
H CH3 CH3 H H 5-cloro-3-piridazinilo
1291
H CH3 CH3 H H 6-cloro-3-piridazinilo
1292
H CH3 CH3 H H 2-bromo-3-piridazinilo
1293
H CH3 CH3 H H 5-bromo-3-piridazinilo
1294
H CH3 CH3 H H 6-bromo-3-piridazinilo
1295
H CH3 CH3 H H 2-metoxi-3-piridazinilo
1296
H CH3 CH3 H H 5-metoxi-3-piridazinilo
1297
H CH3 CH3 H H 6-metoxi-3-piridazinilo
1298
H CH3 CH3 H H 2-trifluorometoxi-3-piridazinilo
1299
H CH3 CH3 H H 5-trifluorometoxi-3-piridazinilo
1300
H CH3 CH3 H H 6-trifluorometoxi-3-piridazinilo
1301
H CH3 CH3 H H 2-metil-3-piridazinilo
1302
H CH3 CH3 H H 5-metil-3-piridazinilo
1303
H CH3 CH3 H H 6-metil-3-piridazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1304
H CH3 CH3 H H 2-trifluorometil-3-piridazinilo
1305
H CH3 CH3 H H 5-trifluorometil-3-piridazinilo
1306
H CH3 CH3 H H 6-trifluorometil-3-piridazinilo
1307
H CH3 CH3 H H 2-ciano-3-piridazinilo
1308
H CH3 CH3 H H 5-ciano-3-piridazinilo
1309
H CH3 CH3 H H 6-ciano-3-piridazinilo
1310
H CH3 CH3 H H 2-nitro-3-piridazinilo
1311
H CH3 CH3 H H 5-nitro-3-piridazinilo
1312
H CH3 CH3 H H 6-nitro-3-piridazinilo
1313
H CH3 CH3 H H 2-metanosulfonil-3-piridazinilo
1314
H CH3 CH3 H H 5-metanosulfonil-3-piridazinilo
1315
H CH3 CH3 H H 6-metanosulfonil-3-piridazinilo
1316
H CH3 CH3 H H 2-pirimidilo
1317
H CH3 CH3 H H 4-fluoro-2-pirimidilo
1318
H CH3 CH3 H H 5-fluoro-2-pirimidilo
1319
H CH3 CH3 H H 4-cloro-2-pirimidilo
1320
H CH3 CH3 H H 5-cloro-2-pirimidilo
1321
H CH3 CH3 H H 4-bromo-2-pirimidilo
1322
H CH3 CH3 H H 5-bromo-2-pirimidilo
1323
H CH3 CH3 H H 4-metoxi-2-pirimidilo
1324
H CH3 CH3 H H 5-metoxi-2-pirimidilo
1325
H CH3 CH3 H H 4-trifluorometoxi-2-pirimidilo
1326
H CH3 CH3 H H 5-trifluorometoxi-2-pirimidilo
1327
H CH3 CH3 H H 4-metil-2-pirimidilo
1328
H CH3 CH3 H H 5-metil-2-pirimidilo
1329
H CH3 CH3 H H 4-trifluorometil-2-pirimidilo
1330
H CH3 CH3 H H 5-trifluorometil-2-pirimidilo
1331
H CH3 CH3 H H 4-ciano-2-pirimidilo
1332
H CH3 CH3 H H 5-ciano-2-pirimidilo
1333
H CH3 CH3 H H 4-nitro-2-pirimidilo
1334
H CH3 CH3 H H 5-nitro-2-pirimidilo
1335
H CH3 CH3 H H 4-metanosulfonil-2-pirimidilo
1336
H CH3 CH3 H H 5-metanosulfonil-2-pirimidilo
1337
H CH3 CH3 H H 4-pirimidilo
1338
H CH3 CH3 H H 2-fluoro-4-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1339
H CH3 CH3 H H 5-fluoro-4-pirimidilo
1340
H CH3 CH3 H H 6-fluoro-4-pirimidilo
1341
H CH3 CH3 H H 2-cloro-4-pirimidilo
1342
H CH3 CH3 H H 5-cloro-4-pirimidilo
1343
H CH3 CH3 H H 6-cloro-4-pirimidilo
1344
H CH3 CH3 H H 2-bromo-4-pirimidilo
1345
H CH3 CH3 H H 5-bromo-4-pirimidilo
1346
H CH3 CH3 H H 6-bromo-4-pirimidilo
1347
H CH3 CH3 H H 2-metoxi-4-pirimidilo
1348
H CH3 CH3 H H 5-metoxi-4-pirimidilo
1349
H CH3 CH3 H H 6-metoxi-4-pirimidilo
1350
H CH3 CH3 H H 2-trifluorometoxi-4-pirimidilo
1351
H CH3 CH3 H H 5-trifluorometoxi-4-pirimidilo
1352
H CH3 CH3 H H 6-trifluorometoxi-4-pirimidilo
1353
H CH3 CH3 H H 2-metil-4-pirimidilo
1354
H CH3 CH3 H H 5-metil-4-pirimidilo
1355
H CH3 CH3 H H 6-metil-4-pirimidilo
1356
H CH3 CH3 H H 2-trifluorometil-4-pirimidilo
1357
H CH3 CH3 H H 5-trifluorometil-4-pirimidilo
1358
H CH3 CH3 H H 6-trifluorometil-4-pirimidilo
1359
H CH3 CH3 H H 2-ciano-4-pirimidilo
1360
H CH3 CH3 H H 5-ciano-4-pirimidilo
1361
H CH3 CH3 H H 6-ciano-4-pirimidilo
1362
H CH3 CH3 H H 2-nitro-4-pirimidilo
1363
H CH3 CH3 H H 5-nitro-4-pirimidilo
1364
H CH3 CH3 H H 6-nitro-4-pirimidilo
1365
H CH3 CH3 H H 2-metanosulfonil-4-pirimidilo
1366
H CH3 CH3 H H 5-metanosulfonil-4-pirimidilo
1367
H CH3 CH3 H H 6-metanosulfonil-4-pirimidilo
1368
H CH3 CH3 H H 5-pirimidilo
1369
H CH3 CH3 H H 2-fluoro-5-pirimidilo
1370
H CH3 CH3 H H 4-fluoro-5-pirimidilo
1371
H CH3 CH3 H H 2-cloro-5-pirimidilo
1372
H CH3 CH3 H H 4-cloro-5-pirimidilo
1373
H CH3 CH3 H H 2-bromo-5-pirimidilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1374
H CH3 CH3 H H 4-bromo-5-pirimidilo
1375
H CH3 CH3 H H 2-metoxi-5-pirimidilo
1376
H CH3 CH3 H H 4-metoxi-5-pirimidilo
1377
H CH3 CH3 H H 2-trifluorometoxi-5-pirimidilo
1378
H CH3 CH3 H H 4-trifluorometoxi-5-pirimidilo
1379
H CH3 CH3 H H 2-metil-5-pirimidilo
1380
H CH3 CH3 H H 4-metil-5-pirimidilo
1381
H CH3 CH3 H H 2-trifluorometil-5-pirimidilo
1382
H CH3 CH3 H H 4-trifluorometil-5-pirimidilo
1383
H CH3 CH3 H H 2-ciano-5-pirimidilo
1384
H CH3 CH3 H H 4-ciano-5-pirimidilo
1385
H CH3 CH3 H H 2-nitro-5-pirimidilo
1386
H CH3 CH3 H H 4-nitro-5-pirimidilo
1387
H CH3 CH3 H H 2-metanosulfonil-5-pirimidilo
1388
H CH3 CH3 H H 4-metanosulfonil-5-pirimidilo
1389
H CH3 CH3 H H 2-pirazinilo
1390
H CH3 CH3 H H 3-fluoro-2-pirazinilo
1391
H CH3 CH3 H H 5-fluoro-2-pirazinilo
1392
H CH3 CH3 H H 6-fluoro-2-pirazinilo
1393
H CH3 CH3 H H 3-cloro-2-pirazinilo
1394
H CH3 CH3 H H 5-cloro-2-pirazinilo
1395
H CH3 CH3 H H 6-cloro-2-pirazinilo
1396
H CH3 CH3 H H 3-bromo-2-pirazinilo
1397
H CH3 CH3 H H 5-bromo-2-pirazinilo
1398
H CH3 CH3 H H 6-bromo-2-pirazinilo
1399
H CH3 CH3 H H 3-metoxi-2-pirazinilo
1400
H CH3 CH3 H H 5-metoxi-2-pirazinilo
1401
H CH3 CH3 H H 6-metoxi-2-pirazinilo
1402
H CH3 CH3 H H 3-trifluorometoxi-2-pirazinilo
1403
H CH3 CH3 H H 5-trifluorometoxi-2-pirazinilo
1404
H CH3 CH3 H H 6-trifluorometoxi-2-pirazinilo
1405
H CH3 CH3 H H 3-metil-2-pirazinilo
1406
H CH3 CH3 H H 5-metil-2-pirazinilo
1407
H CH3 CH3 H H 6-metil-2-pirazinilo
1408
H CH3 CH3 H H 3-trifluorometil-2-pirazinilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1409
H CH3 CH3 H H 5-trifluorometil-2-pirazinilo
1410
H CH3 CH3 H H 6-trifluorometil-2-pirazinilo
1411
H CH3 CH3 H H 3-ciano-2-pirazinilo
1412
H CH3 CH3 H H 5-ciano-2-pirazinilo
1413
H CH3 CH3 H H 6-ciano-2-pirazinilo
1414
H CH3 CH3 H H 3-nitro-2-pirazinilo
1415
H CH3 CH3 H H 5-nitro-2-pirazinilo
1416
H CH3 CH3 H H 6-nitro-2-pirazinilo
1417
H CH3 CH3 H H 3-metilsulfonato-2-pirazinilo
1418
H CH3 CH3 H H 5-metilsulfonato-2-pirazinilo
1419
H CH3 CH3 H H 6-metilsulfonato-2-pirazinilo
1420
H CH3 CH3 H H 2-furanilo
1421
H CH3 CH3 H H 3-fluoro-2-furanilo
1422
H CH3 CH3 H H 4-fluoro-2-furanilo
1423
H CH3 CH3 H H 5-fluoro-2-furanilo
1424
H CH3 CH3 H H 3-cloro-2-furanilo
1425
H CH3 CH3 H H 4-cloro-2-furanilo
1426
H CH3 CH3 H H 5-cloro-2-furanilo
1427
H CH3 CH3 H H 3-bromo-2-furanilo
1428
H CH3 CH3 H H 4-bromo-2-furanilo
1429
H CH3 CH3 H H 5-bromo-2-furanilo
1430
H CH3 CH3 H H 3-metoxi-2-furanilo
1431
H CH3 CH3 H H 4-metoxi-2-furanilo
1432
H CH3 CH3 H H 5-metoxi-2-furanilo
1433
H CH3 CH3 H H 3-trifluorometoxi-2-furanilo
1434
H CH3 CH3 H H 4-trifluorometoxi-2-furanilo
1435
H CH3 CH3 H H 5-trifluorometoxi-2-furanilo
1436
H CH3 CH3 H H 3-metil-2-furanilo
1437
H CH3 CH3 H H 4-metil-2-furanilo
1438
H CH3 CH3 H H 5-metil-2-furanilo
1439
H CH3 CH3 H H 3-trifluorometil-2-furanilo
1440
H CH3 CH3 H H 4-trifluorometil-2-furanilo
1441
H CH3 CH3 H H 5-trifluorometil-2-furanilo
1442
H CH3 CH3 H H 3-ciano-2-furanilo
1443
H CH3 CH3 H H 4-ciano-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1444
H CH3 CH3 H H 5-ciano-2-furanilo
1445
H CH3 CH3 H H 3-nitro-2-furanilo
1446
H CH3 CH3 H H 4-nitro-2-furanilo
1447
H CH3 CH3 H H 5-nitro-2-furanilo
1448
H CH3 CH3 H H 3-metanosulfonil-2-furanilo
1449
H CH3 CH3 H H 4-metanosulfonil-2-furanilo
1450
H CH3 CH3 H H 5-metanosufonil-2-furanilo
1451
H CH3 CH3 H H 3-furanilo
1452
H CH3 CH3 H H 3-fluoro-2-furanilo
1453
H CH3 CH3 H H 4-fluoro-2-furanilo
1454
H CH3 CH3 H H 5-fluoro-2-furanilo
1455
H CH3 CH3 H H 3-cloro-2-furanilo
1456
H CH3 CH3 H H 4-cloro-2-furanilo
1457
H CH3 CH3 H H 5-cloro-2-furanilo
1458
H CH3 CH3 H H 3-bromo-2-furanilo
1459
H CH3 CH3 H H 4-bromo-2-furanilo
1460
H CH3 CH3 H H 5-bromo-2-furanilo
1461
H CH3 CH3 H H 3-metoxi-2-furanilo
1462
H CH3 CH3 H H 4-metoxi-2-furanilo
1463
H CH3 CH3 H H 5-metoxi-2-furanilo
1464
H CH3 CH3 H H 3-trifluorometoxi-2-furanilo
1465
H CH3 CH3 H H 4-trifluorometoxi-2-furanilo
1466
H CH3 CH3 H H 5-trifluorometoxi-2-furanilo
1467
H CH3 CH3 H H 3-metil-2-furanilo
1468
H CH3 CH3 H H 4-metil-2-furanilo
1469
H CH3 CH3 H H 5-metil-2-furanilo
1470
H CH3 CH3 H H 3-trifluorometil-2-furanilo
1471
H CH3 CH3 H H 4-trifluorometil-2-furanilo
1472
H CH3 CH3 H H 5-trifluorometil-2-furanilo
1473
H CH3 CH3 H H 3-ciano-2-furanilo
1474
H CH3 CH3 H H 4-ciano-2-furanilo
1475
H CH3 CH3 H H 5-ciano-2-furanilo
1476
H CH3 CH3 H H 3-nitro-2-furanilo
1477
H CH3 CH3 H H 4-nitro-2-furanilo
1478
H CH3 CH3 H H 5-nitro-2-furanilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1479
H CH3 CH3 H H 3-metanosulfonil-2-furanilo
1480
H CH3 CH3 H H 4-metanosulfonil-2-furanilo
1481
H CH3 CH3 H H 5-metanosufonil-2-furanilo
1482
H CH3 CH3 H H 3-furanilo
1483
H CH3 CH3 H H 2-fluoro-3-furanilo
1484
H CH3 CH3 H H 4-fluoro-3-furanilo
1485
H CH3 CH3 H H 5-fluoro-3-furanilo
1486
H CH3 CH3 H H 2-cloro-3-furanilo
1487
H CH3 CH3 H H 4-cloro-3-furanilo
1488
H CH3 CH3 H H 5-cloro-3-furanilo
1489
H CH3 CH3 H H 2-bromo-3-furanilo
1490
H CH3 CH3 H H 4-bromo-3-furanilo
1491
H CH3 CH3 H H 5-bromo-3-furanilo
1492
H CH3 CH3 H H 2-metoxi-3-furanilo
1493
H CH3 CH3 H H 4-metoxi-3-furanilo
1494
H CH3 CH3 H H 5-metoxi-3-furanilo
1495
H CH3 CH3 H H 2-trifluorometoxi-3-furanilo
1496
H CH3 CH3 H H 4-trifluorometoxi-3-furanilo
1497
H CH3 CH3 H H 5-trifluorometoxi-3-furanilo
1498
H CH3 CH3 H H 2-metil-3-furanilo
1499
H CH3 CH3 H H 4-metil-3-furanilo
1500
H CH3 CH3 H H 5-metil-3-furanilo
1501
H CH3 CH3 H H 2-trifluorometil-3-furanilo
1502
H CH3 CH3 H H 4-trifluorometil-3-furanilo
1503
H CH3 CH3 H H 5-trifluorometil-3-furanilo
1504
H CH3 CH3 H H 2-ciano-3-furanilo
1505
H CH3 CH3 H H 4-ciano-3-furanilo
1506
H CH3 CH3 H H 5-ciano-3-furanilo
1507
H CH3 CH3 H H 2-nitro-3-furanilo
1508
H CH3 CH3 H H 4-nitro-3-furanilo
1509
H CH3 CH3 H H 5-nitro-3-furanilo
1510
H CH3 CH3 H H 2-metanosulfonil-3-furanilo
1511
H CH3 CH3 H H 4-metanosulfonil-3-furanilo
1512
H CH3 CH3 H H 5-metanosufonil-3-furanilo
1513
H CH3 CH3 H H 2-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1514
H CH3 CH3 H H 3-fluoro-2-tiofenilo
1515
H CH3 CH3 H H 4-fluoro-2-tiofenilo
1516
H CH3 CH3 H H 5-fluoro-2-tiofenilo
1517
H CH3 CH3 H H 3-cloro-2-tiofenilo
1518
H CH3 CH3 H H 4-cloro-2-tiofenilo
1519
H CH3 CH3 H H 5-cloro-2-tiofenilo
1520
H CH3 CH3 H H 3-bromo-2-tiofenilo
1521
H CH3 CH3 H H 4-bromo-2-tiofenilo
1522
H CH3 CH3 H H 5-bromo-2-tiofenilo
1523
H CH3 CH3 H H 3-metoxi-2-tiofenilo
1524
H CH3 CH3 H H 4-metoxi-2-tiofenilo
1525
H CH3 CH3 H H 5-metoxi-2-tiofenilo
1526
H CH3 CH3 H H 3-trifluorometoxi-2-tiofenilo
1527
H CH3 CH3 H H 4-trifluorometoxi-2-tiofenilo
1528
H CH3 CH3 H H 5-trifluorometoxi-2-tiofenilo
1529
H CH3 CH3 H H 3-metil-2-tiofenilo
1530
H CH3 CH3 H H 4-metil-2-tiofenilo
1531
H CH3 CH3 H H 5-metil-2-tiofenilo
1532
H CH3 CH3 H H 3-trifluorometil-2-tiofenilo
1533
H CH3 CH3 H H 4-trifluorometil-2-tiofenilo
1534
H CH3 CH3 H H 5-trifluorometil-2-tiofenilo
1535
H CH3 CH3 H H 3-ciano-2-tiofenilo
1536
H CH3 CH3 H H 4-ciano-2-tiofenilo
1537
H CH3 CH3 H H 5-ciano-2-tiofenilo
1538
H CH3 CH3 H H 3-nitro-2-tiofenilo
1539
H CH3 CH3 H H 4-nitro-2-tiofenilo
1540
H CH3 CH3 H H 5-nitro-2-tiofenilo
1541
H CH3 CH3 H H 3-metanosulfonil-2-tiofenilo
1542
H CH3 CH3 H H 4-metanosulfonil-2-tiofenilo
1543
H CH3 CH3 H H 5-metanosufonil-2-tiofenilo
1544
H CH3 CH3 H H 3-tiofenilo
1545
H CH3 CH3 H H 3-fluoro-2-tiofenilo
1546
H CH3 CH3 H H 4-fluoro-2-tiofenilo
1547
H CH3 CH3 H H 5-fluoro-2-tiofenilo
1548
H CH3 CH3 H H 3-cloro-2-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1549
H CH3 CH3 H H 4-cloro-2-tiofenilo
1550
H CH3 CH3 H H 5-cloro-2-tiofenilo
1551
H CH3 CH3 H H 3-bromo-2-tiofenilo
1552
H CH3 CH3 H H 4-bromo-2-tiofenilo
1553
H CH3 CH3 H H 5-bromo-2-tiofenilo
1554
H CH3 CH3 H H 3-metoxi-2-tiofenilo
1555
H CH3 CH3 H H 4-metoxi-2-tiofenilo
1556
H CH3 CH3 H H 5-metoxi-2-tiofenilo
1557
H CH3 CH3 H H 3-trifluorometoxi-2-tiofenilo
1558
H CH3 CH3 H H 4-trifluorometoxi-2-tiofenilo
1559
H CH3 CH3 H H 5-trifluorometoxi-2-tiofenilo
1560
H CH3 CH3 H H 3-metil-2-tiofenilo
1561
H CH3 CH3 H H 4-metil-2-tiofenilo
1562
H CH3 CH3 H H 5-metil-2-tiofenilo
1563
H CH3 CH3 H H 3-trifluorometil-2-tiofenilo
1564
H CH3 CH3 H H 4-trifluorometil-2-tiofenilo
1565
H CH3 CH3 H H 5-trifluorometil-2-tiofenilo
1566
H CH3 CH3 H H 3-ciano-2-tiofenilo
1567
H CH3 CH3 H H 4-ciano-2-tiofenilo
1568
H CH3 CH3 H H 5-ciano-2-tiofenilo
1569
H CH3 CH3 H H 3-nitro-2-tiofenilo
1570
H CH3 CH3 H H 4-nitro-2-tiofenilo
1571
H CH3 CH3 H H 5-nitro-2-tiofenilo
1572
H CH3 CH3 H H 3-metanosulfonil-2-tiofenilo
1573
H CH3 CH3 H H 4-metanosulfonil-2-tiofenilo
1574
H CH3 CH3 H H 5-metanosufonil-2-tiofenilo
1575
H CH3 CH3 H H 3-tiofenilo
1576
H CH3 CH3 H H 2-fluoro-3-tiofenilo
1577
H CH3 CH3 H H 4-fluoro-3-tiofenilo
1578
H CH3 CH3 H H 5-fluoro-3-tiofenilo
1579
H CH3 CH3 H H 2-cloro-3-tiofenilo
1580
H CH3 CH3 H H 4-cloro-3-tiofenilo
1581
H CH3 CH3 H H 5-cloro-3-tiofenilo
1582
H CH3 CH3 H H 2-bromo-3-tiofenilo
1583
H CH3 CH3 H H 4-bromo-3-tiofenilo
Compuesto número
R5 R6 R7 R8 R9 HetAr
1584
H CH3 CH3 H H 5-bromo-3-tiofenilo
1585
H CH3 CH3 H H 2-metoxi-3-tiofenilo
1586
H CH3 CH3 H H 4-metoxi-3-tiofenilo
1587
H CH3 CH3 H H 5-metoxi-3-tiofenilo
1588
H CH3 CH3 H H 2-trifluorometoxi-3-tiofenilo
1589
H CH3 CH3 H H 4-trifluorometoxi-3-tiofenilo
1590
H CH3 CH3 H H 5-trifluorometoxi-3-tiofenilo
1591
H CH3 CH3 H H 2-metil-3-tiofenilo
1592
H CH3 CH3 H H 4-metil-3-tiofenilo
1593
H CH3 CH3 H H 5-metil-3-tiofenilo
1594
H CH3 CH3 H H 2-trifluorometil-3-tiofenilo
1595
H CH3 CH3 H H 4-trifluorometil-3-tiofenilo
1596
H CH3 CH3 H H 5-trifluorometil-3-tiofenilo
1597
H CH3 CH3 H H 2-ciano-3-tiofenilo
1598
H CH3 CH3 H H 4-ciano-3-tiofenilo
1599
H CH3 CH3 H H 5-ciano-3-tiofenilo
1600
H CH3 CH3 H H 2-nitro-3-tiofenilo
1601
H CH3 CH3 H H 4-nitro-3-tiofenilo
1602
H CH3 CH3 H H 5-nitro-3-tiofenilo
1603
H CH3 CH3 H H 2-metanosulfonil-3-tiofenilo
1604
H CH3 CH3 H H 4-metanosulfonil-3-tiofenilo
1605
H CH3 CH3 H H 5-metanosufonil-3-tiofenilo
1606
H CH3 CH3 H H 2-ozaxol
1607
H CH3 CH3 H H 4-fluoro-2-ozaxol
1608
H CH3 CH3 H H 5-fluoro-2-ozaxol
1609
H CH3 CH3 H H 4-cloro-2-ozaxol
1610
H CH3 CH3 H H 5-cloro-2-ozaxol
1611
H CH3 CH3 H H 4-bromo-2-ozaxol
1612
H CH3 CH3 H H 5-bromo-2-ozaxol
1613
H CH3 CH3 H H 4-metoxi-2-ozaxol
1614
H CH3 CH3 H H 5-metoxi-2-ozaxol
1615
H CH3 CH3 H H 4-trifluorometoxi-2-ozaxol
1616
H CH3 CH3 H H 5-trifluorometoxi-2-ozaxol
1617
H CH3 CH3 H H 4-metil-2-ozaxol
1618
H CH3 CH3 H H 5-metil-2-ozaxol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1619
H CH3 CH3 H H 4-trifluorometil-2-ozaxol
1620
H CH3 CH3 H H 5-trifluorometil-2-ozaxol
1621
H CH3 CH3 H H 4-ciano-2-ozaxol
1622
H CH3 CH3 H H 5-ciano-2-ozaxol
1623
H CH3 CH3 H H 4-nitro-2-ozaxol
1624
H CH3 CH3 H H 5-nitro-2-ozaxol
1625
H CH3 CH3 H H 4-metanosulfonil-2-ozaxol
1626
H CH3 CH3 H H 5-metanosulfonil-2-ozaxol
1627
H CH3 CH3 H H 4-ozaxol
1628
H CH3 CH3 H H 2-fluoro-4-ozaxol
1629
H CH3 CH3 H H 5-fluoro-4-ozaxol
1630
H CH3 CH3 H H 2-cloro-4-ozaxol
1631
H CH3 CH3 H H 5-cloro-4-ozaxol
1632
H CH3 CH3 H H 2-bromo-4-ozaxol
1633
H CH3 CH3 H H 5-bromo-4-ozaxol
1634
H CH3 CH3 H H 2-metoxi-4-ozaxol
1635
H CH3 CH3 H H 5-metoxi-4-ozaxol
1636
H CH3 CH3 H H 2-trifluorometoxi-4-ozaxol
1637
H CH3 CH3 H H 5-trifluorometoxi-4-ozaxol
1638
H CH3 CH3 H H 2-metil-4-ozaxol
1639
H CH3 CH3 H H 5-metil-4-ozaxol
1640
H CH3 CH3 H H 4-trifluorometil-4-ozaxol
1641
H CH3 CH3 H H 5-trifluorometil-4-ozaxol
1642
H CH3 CH3 H H 4-ciano-4-ozaxol
1643
H CH3 CH3 H H 5-ciano-4-ozaxol
1644
H CH3 CH3 H H 4-nitro-4-ozaxol
1645
H CH3 CH3 H H 5-nitro-4-ozaxol
1646
H CH3 CH3 H H 4-metanosulfonil-4-ozaxol
1647
H CH3 CH3 H H 5-metanosulfonil-4-ozaxol
1648
H CH3 CH3 H H 5-ozaxol
1649
H CH3 CH3 H H 2-fluoro-5-ozaxol
1650
H CH3 CH3 H H 4-fluoro-5-ozaxol
1651
H CH3 CH3 H H 2-cloro-5-ozaxol
1652
H CH3 CH3 H H 4-cloro-5-ozaxol
1653
H CH3 CH3 H H 2-bromo-5-ozaxol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1654
H CH3 CH3 H H 4-bromo-5-ozaxol
1655
H CH3 CH3 H H 2-metoxi-5-ozaxol
1656
H CH3 CH3 H H 4-metoxi-5-ozaxol
1657
H CH3 CH3 H H 2-trifluorometoxi-5-ozaxol
1658
H CH3 CH3 H H 4-trifluorometoxi-5-ozaxol
1659
H CH3 CH3 H H 2-metil-5-ozaxol
1660
H CH3 CH3 H H 4-metil-5-ozaxol
1661
H CH3 CH3 H H 2-trifluorometil-5-ozaxol
1662
H CH3 CH3 H H 4-trifluorometil-5-ozaxol
1663
H CH3 CH3 H H 2-ciano-5-ozaxol
1664
H CH3 CH3 H H 4-ciano-5-ozaxol
1665
H CH3 CH3 H H 2-nitro-5-ozaxol
1666
H CH3 CH3 H H 4-nitro-5-ozaxol
1667
H CH3 CH3 H H 2-metanosulfonil-5-ozaxol
1668
H CH3 CH3 H H 4-metanosulfonil-5-ozaxol
1669
H CH3 CH3 H H 2-tiazol
1670
H CH3 CH3 H H 4-fluoro-2-tiazol
1671
H CH3 CH3 H H 5-fluoro-2-tiazol
1672
H CH3 CH3 H H 4-cloro-2-tiazol
1673
H CH3 CH3 H H 5-cloro-2-tiazol
1674
H CH3 CH3 H H 4-bromo-2-tiazol
1675
H CH3 CH3 H H 5-bromo-2-tiazol
1676
H CH3 CH3 H H 4-metoxi-2-tiazol
1677
H CH3 CH3 H H 5-metoxi-2-tiazol
1678
H CH3 CH3 H H 4-trifluorometoxi-2-tiazol
1679
H CH3 CH3 H H 5-trifluorometoxi-2-tiazol
1680
H CH3 CH3 H H 4-metil-2-tiazol
1681
H CH3 CH3 H H 5-metil-2-tiazol
1682
H CH3 CH3 H H 4-trifluorometil-2-tiazol
1683
H CH3 CH3 H H 5-trifluorometil-2-tiazol
1684
H CH3 CH3 H H 4-ciano-2-tiazol
1685
H CH3 CH3 H H 5-ciano-2-tiazol
1686
H CH3 CH3 H H 4-nitro-2-tiazol
1687
H CH3 CH3 H H 5-nitro-2-tiazol
1688
H CH3 CH3 H H 4-metanosulfonil-2-tiazol
Compuesto número
R5 R6 R7 R8 R9 HetAr
1689
H CH3 CH3 H H 5-metanosulfonil-2-tiazol
1690
H CH3 CH3 H H 4-tiazol
1691
H CH3 CH3 H H 2-fluoro-4-tiazol
1692
H CH3 CH3 H H 5-fluoro-4-tiazol
1693
H CH3 CH3 H H 2-cloro-4-tiazol
1694
H CH3 CH3 H H 5-cloro-4-tiazol
1695
H CH3 CH3 H H 2-bromo-4-tiazol
1696
H CH3 CH3 H H 5-bromo-4-tiazol
1697
H CH3 CH3 H H 2-metoxi-4-tiazol
1698
H CH3 CH3 H H 5-metoxi-4-tiazol
1699
H CH3 CH3 H H 2-trifluorometoxi-4-tiazol
1700
H CH3 CH3 H H 5-trifluorometoxi-4-tiazol
1701
H CH3 CH3 H H 2-metil-4-tiazol
1702
H CH3 CH3 H H 5-metil-4-tiazol
1703
H CH3 CH3 H H 4-trifluorometil-4-tiazol
1704
H CH3 CH3 H H 5-trifluorometil-4-tiazol
1705
H CH3 CH3 H H 4-ciano-4-tiazol
1706
H CH3 CH3 H H 5-ciano-4-tiazol
1707
H CH3 CH3 H H 4-nitro-4-tiazol
1708
H CH3 CH3 H H 5-nitro-4-tiazol
1709
H CH3 CH3 H H 4-metanosulfonil-4-tiazol
1710
H CH3 CH3 H H 5-metanosulfonil-4-tiazol
1711
H CH3 CH3 H H 5-tiazol
1712
H CH3 CH3 H H 2-fluoro-5-tiazol
1713
H CH3 CH3 H H 4-fluoro-5-tiazol
1714
H CH3 CH3 H H 2-cloro-5-tiazol
1715
H CH3 CH3 H H 4-cloro-5-tiazol
1716
H CH3 CH3 H H 2-bromo-5-tiazol
1717
H CH3 CH3 H H 4-bromo-5-tiazol
1718
H CH3 CH3 H H 2-metoxi-5-tiazol
1719
H CH3 CH3 H H 4-metoxi-5-tiazol
1720
H CH3 CH3 H H 2-trifluorometoxi-5-tiazol
1721
H CH3 CH3 H H 4-trifluorometoxi-5-tiazol
1722
H CH3 CH3 H H 2-metil-5-tiazol
1723
H CH3 CH3 H H 4-metil-5-tiazol
imagen56
imagen57
imagen58
imagen59

Claims (7)

  1. imagen1
    imagen2
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    128
    imagen8
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    imagen11
    imagen12
    imagen13
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  2. 14.
    Una composición herbicida según la reivindicación 13, que, además de comprender auxiliares de la formulación, comprende una cantidad herbicidamente eficaz del compuesto de fórmula I, un herbicida adicional, y opcionalmente un protector.
  3. 15.
    Una composición herbicida según la reivindicación 13, que, además de comprender auxiliares de la formulación, comprende una cantidad herbicidamente eficaz del compuesto de fórmula I, un protector, y opcionalmente un herbicida adicional.
  4. 16.
    Un método para controlar hierbas y malas hierbas en cultivos de plantas útiles, que comprende aplicar una cantidad herbicidamente eficaz de un compuesto de fórmula I como se define en cualquiera de las reivindicaciones 1 a 8, o de una composición que comprende tal compuesto, a las plantas o a su locus.
  5. 17.
    Un método según la reivindicación 16, que es un método para controlar hierbas y malas hierbas en cultivo de plantas útiles, que comprende aplicar una cantidad herbicidamente eficaz de una composición que comprende el compuesto de fórmula I a las plantas o a su locus, y en el que
    los cultivos de plantas útiles son trigo, cebada, arroz, maíz, colza, remolacha, caña de azúcar, haba de soja, algodón, girasol, o cacahuete.
  6. 18.
    Un método según la reivindicación 17, en el que los cultivos de plantas útiles son trigo o cebada.
  7. 19.
    Una mezcla de un compuesto de fórmula I, como se define en cualquiera de las reivindicaciones 1 a 8, en combinación con un herbicida adicional, en el que la mezcla del compuesto de fórmula I se selecciona de:
    compuesto de fórmula I + acetoclor, compuesto de fórmula I + acifluorfen, compuesto de fórmula I + acifluorfensodio, compuesto de fórmula I + aclonifen, compuesto de fórmula I + acroleína, compuesto de fórmula I + alaclor, compuesto de fórmula I + aloxidim, compuesto de fórmula I + alcohol alílico, compuesto de fórmula I + ametrina, compuesto de fórmula I + amicarbazona, compuesto de fórmula I + amidosulfurón, compuesto de fórmula I + aminopiralida, compuesto de fórmula I + amitrol, compuesto de fórmula I + sulfamato de amonio, compuesto de fórmula I + anilofós, compuesto de fórmula I + asulam, compuesto de fórmula I + atratón, compuesto de fórmula I + atrazina, compuesto de fórmula I + azimsulfurón, compuesto de fórmula I + BCPC, compuesto de fórmula I + beflubutamida, compuesto de fórmula I + benazolina, compuesto de fórmula I + benfluralina, compuesto de fórmula I + benfuresato, compuesto de fórmula I + bensulfurón, compuesto de fórmula I + bensulfurón-metilo, compuesto de fórmula I + bensulida, compuesto de fórmula I + bentazona, compuesto de fórmula I + benzfendizona, compuesto de fórmula I + benzobiciclón, compuesto de fórmula I + benzofenap, compuesto de fórmula I + bifenox, compuesto de fórmula I + bilanafós, compuesto de fórmula I + bispiribac, compuesto de fórmula I + bispiribac-sodio, compuesto de fórmula I + bórax, compuesto de fórmula I + bromacilo, compuesto de fórmula I + bromobutida, compuesto de fórmula I + bromoxinilo, compuesto de fórmula I + butaclor, compuesto de fórmula I + butafenacilo, compuesto de fórmula I + butamifós, compuesto de fórmula I + butralina, compuesto de fórmula I + butroxidim, compuesto de fórmula I + butilato, compuesto de fórmula I + ácido cacodílico, compuesto de fórmula I + clorato de calcio, compuesto de fórmula I + cafenstrol, compuesto de fórmula I + carbetamida, compuesto de fórmula I + carfentrazona, compuesto de fórmula I + carfentrazona-etilo, compuesto de fórmula I + CDEA, compuesto de fórmula I + CEPC, compuesto de fórmula I + clorflurenol, compuesto de fórmula I + clorflurenol-metilo, compuesto de fórmula I + cloridazón, compuesto de fórmula I + clorimurón, compuesto de fórmula I + clorimurón-etilo, compuesto de fórmula I + ácido cloroacético, compuesto de fórmula I + clorotolurón, compuesto de fórmula I + clorprofam, compuesto de fórmula I + clorsulfurón, compuesto de fórmula I + clortal, compuesto de fórmula I + clortal-dimetilo, compuesto de fórmula I + cinidón-etilo, compuesto de fórmula I + cinmetilina, compuesto de fórmula I + cinosulfurón, compuesto de fórmula I + cisanilida, compuesto de fórmula I + cletodim, compuesto de fórmula I + clodinafop, compuesto de fórmula I + clodinafop-propargilo, compuesto de fórmula I + clomazona, compuesto de fórmula I + clomeprop, compuesto de fórmula I + clopiralida, compuesto de fórmula I + cloransulam, compuesto de fórmula I + cloransulam-metilo, compuesto de fórmula I + CMA, compuesto de fórmula I + 4-CPB, compuesto de fórmula I + CPMF, compuesto de fórmula I + 4-CPP, compuesto de fórmula I + CPPC, compuesto de fórmula I + cresol, compuesto de fórmula I + cumilurón, compuesto de fórmula I + cianamida, compuesto de fórmula I + cianazina, compuesto de fórmula I + cicloato, compuesto de fórmula I + ciclosulfamurón, compuesto de fórmula I + cicloxidim, compuesto de fórmula I + cihalofop, compuesto de fórmula I + cihalofop-butilo, compuesto de fórmula I + 2,4-D, compuesto de fórmula I + 3,4-DA, compuesto de fórmula I + daimurón, compuesto de fórmula I + dalapón, compuesto de fórmula I + dazomet, compuesto de fórmula I + 2,4-DB, compuesto de fórmula I + 3,4-DB, compuesto de fórmula I + 2,4-DEB, compuesto de fórmula I
    + desmedifam, compuesto de fórmula I + dicamba, compuesto de fórmula I + diclobenilo, compuesto de fórmula I + orto-diclorobenceno, compuesto de fórmula I + para-diclorobenceno, compuesto de fórmula I + diclorprop, compuesto de fórmula I + diclorprop-P, compuesto de fórmula I + diclofop, compuesto de fórmula I + diclofopmetilo, compuesto de fórmula I + diclosulam, compuesto de fórmula I + difenzoquat, compuesto de fórmula I + metilsulfato de difenzoquat, compuesto de fórmula I + diflufenican, compuesto de fórmula I + diflufenzopir, compuesto de fórmula I + dimefurón, compuesto de fórmula I + dimepiperato, compuesto de fórmula I + dimetaclor, compuesto de fórmula I + dimetametrin, compuesto de fórmula I + dimetenamid, compuesto de fórmula I + dimetenamid-P, compuesto de fórmula I + dimetipin, compuesto de fórmula I + ácido dimetilarsínico, compuesto de fórmula I + dinitramina, compuesto de fórmula I + dinoterb, compuesto de fórmula I + difenamid,
    137
    imagen16
    piriftalida, compuesto de fórmula I + piriminobac, compuesto de fórmula I + piriminobac-metilo, compuesto de fórmula I + pirimisulfan, compuesto de fórmula I + piritiobac, compuesto de fórmula I + piritiobac-sodio, compuesto de fórmula I + quinclorac, compuesto de fórmula I + quinmerac, compuesto de fórmula I + quinoclamina, compuesto de fórmula I + quizalofop, compuesto de fórmula I + quizalofop-P, compuesto de fórmula I + rimsulfurón, compuesto de fórmula I + setoxidim, compuesto de fórmula I + sidurón, compuesto de fórmula I + simazina, compuesto de fórmula I + simetrina, compuesto de fórmula I + SMA, compuesto de fórmula I + arsenito de sodio, compuesto de fórmula I + azida sódica, compuesto de fórmula I + clorato de sodio, compuesto de fórmula I + sulcotriona, compuesto de fórmula I + sulfentrazona, compuesto de fórmula I + sulfometurón, compuesto de fórmula I + sulfometurón-metilo, compuesto de fórmula I + sulfosato, compuesto de fórmula I + sulfosulfurón, compuesto de fórmula I + ácido sulfúrico, compuesto de fórmula I + aceites de alquitrán, compuesto de fórmula I + 2,3,6-TBA, compuesto de fórmula I + TCA, compuesto de fórmula I + TCA-sodio, compuesto de fórmula I + tebutiurón, compuesto de fórmula I + tepraloxidim, compuesto de fórmula I + terbacilo, compuesto de fórmula I + terbumetón, compuesto de fórmula I + terbutilazina, compuesto de fórmula I + terbutrina, compuesto de fórmula I + tenilclor, compuesto de fórmula I + tiazopir, compuesto de fórmula I + tifensulfurón, compuesto de fórmula I + tifensulfurón-metilo, compuesto de fórmula I + tiobencarb, compuesto de fórmula I + tiocarbazilo, compuesto de fórmula I + topramezona, compuesto de fórmula I + tralkoxidim, compuesto de fórmula I + tri-alato, compuesto de fórmula I + triasulfurón, compuesto de fórmula I + triaziflam, compuesto de fórmula I + tribenurón, compuesto de fórmula I + tribenurón-metilo, compuesto de fórmula I + tricamba, compuesto de fórmula I + triclopir, compuesto de fórmula I + trietazina, compuesto de fórmula I + trifloxisulfurón, compuesto de fórmula I + trifloxisulfurón-sodio, compuesto de fórmula I + trifluralina, compuesto de fórmula I + triflusulfurón, compuesto de fórmula I + triflusulfurón-metilo, compuesto de fórmula I + trihidroxitriazina, compuesto de fórmula I + tritosulfurón, compuesto de fórmula I + éster etílico del ácido [3-[2cloro-4-fluoro-5-(1-metil-6-trifluorometil-2,4-dioxo-1,2,3,4-tetrahidropirimidin-3-il)fenoxi]-2-piridiloxi]acético, compuesto de fórmula I + ácido 4-[(4,5-dihidro-3-metoxi-4-metil-5-oxo)-1H-1,2,4-triazol-1-ilcarbonilsulfamoil]-5metiltiofen-3-carboxílico, compuesto de fórmula I + BAY747 que tiene el número de referencia de Chemical Abstracts Service 335104-84-2, compuesto de fórmula I + topramezona, compuesto de fórmula I + 4-hidroxi-3-[[2[(2-metoxietoxi)metil]-6-(trifluorometil)-3-piridinil]carbonil]-biciclo[3.2.1]oct-3-en-2-ona (, y compuesto de fórmula I
    + 4-hidroxi-3-[[2-(3-metoxipropil)-6-(difluorometil)-3-piridinil]carbonil]-biciclo[3.2.1]oct-3-en-2-ona;
    y en el que la pareja de mezclamiento para el compuesto de fórmula I está opcionalmente en forma de un éster o una sal.
    139
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