ES2565092T3 - Compuestos de ciclohexanona y herbicidas que los comprenden - Google Patents

Compuestos de ciclohexanona y herbicidas que los comprenden Download PDF

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ES2565092T3
ES2565092T3 ES12726909.0T ES12726909T ES2565092T3 ES 2565092 T3 ES2565092 T3 ES 2565092T3 ES 12726909 T ES12726909 T ES 12726909T ES 2565092 T3 ES2565092 T3 ES 2565092T3
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alkyl
aryl
alkoxy
cycloalkyl
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Yosuke NAKASHIMA
Yoshinobu Jin
Masato Konobe
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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Abstract

Un compuesto de ciclohexanona de fórmula (I):**Fórmula** en donde m es un número entero de 1, 2 o 3; n es un número entero de uno cualquiera de 1 a 5; X representa CH2, O, NR9, S, S(O) o S(O)2; R1 representa un átomo de hidrógeno o un grupo metilo; R2 y R3 representan independientemente entre sí un átomo de hidrógeno, un grupo alquilo C1-C6, un grupo haloalquilo C1-C6, un grupo cicloalquilo C3-C8, un grupo halocicloalquilo C3-C9, un grupo (alquil C1- C6)cicloalquilo C3-C8, un grupo (cicloalquil C3-C8)alquilo C1-C6, un grupo (cicloalquil C3-C8)cicloalquilo C3-C8, un grupo (halocicloalquil C3-C8)alquilo C1-C6 o un grupo {(alquil C1-C6)cicloalquil C3-C8}alquilo C1-C6, o R2 y R3 se conectan entre sí para representar una cadena de alquileno C2-C5, o R2 y R3 se combinan entre sí para representar un grupo alquilideno C1-C3 que tiene opcionalmente uno o más átomos de halógeno, con la condición de que cuando m es 2 o 3, dos o tres R2 pueden ser iguales o diferentes entre sí y dos o tres R3 pueden ser iguales o diferentes entre sí; R4 representa un grupo arilo C6-C10 o un grupo heteroarilo de cinco a seis miembros, con la condición de que el grupo arilo C6-C10 y el grupo heteroarilo de cinco a seis miembros pueden tener uno o más sustituyentes seleccionados del grupo que consiste en un átomo de halógeno, un grupo ciano, un grupo nitro, un grupo amino, un grupo (alquil C1-C6)amino, un grupo a (alquil C1-C6)(alquil C1-C6)amino, un grupo benzoilamino, un grupo aminocarbonilo, un grupo (alquil C1-C6)aminocarbonilo, un grupo (alquil C1- C6)(alquil C1-C6)aminocarbonilo, un grupo pentafluorotio, un grupo alquilo C1-C6, un grupo alquenilo C2-C6, un grupo alquinilo C2-C6, un grupo alcoxi C1-C6, un grupo (alquil C1-C6)tio, un grupo (alquenil C3-C6)oxi, un grupo (alquinil C3-C6)oxi, un grupo arilo C6-C10, un grupo aril(C6-C10)oxi, un grupo (alquil C1-C6)sulfinilo, un grupo alquil(C1-C6)sulfonilo, un grupo hidroxilo, un grupo (alquil C1-C6)carbonilo, un grupo hidroxicarbonilo, un grupo (alcoxi C1-C6)carbonilo y un grupo (aril C6-C10)alcoxi C1-C6, y cuando existen dos o más sustituyentes, los sustituyentes pueden ser iguales o diferentes entre sí; y el grupo (alquil C1-C6)amino, el grupo (alquil C1-C6)(alquil C1-C6)amino, el grupo benzoilamino, el grupo (alquil C1-C6)aminocarbonilo, el grupo (alquil C1-C6)(alquil C1-C6)aminocarbonilo, el grupo alquilo C1-C6, el grupo alquenillo C2-C6, el grupo alquinillo C2-C6; el grupo alcoxi C1-C6, el grupo (alquil C1-C6)tio, el grupo (alquenil C3-C6)oxi, el grupo (alquinil C3-C6)oxi, el grupo arilo C6-C10, el grupo (aril C6-C10)oxi, el grupo (alquil C1-C6)sulfinilo, el grupo (alquil C1-C6)sulfonilo, el grupo (alcoxi C1-C6)carbonilo y el grupo (aril C6-C10)alcoxi C1-C6 pueden tener cada uno uno o más átomos de halógeno o grupos haloalquilo C1-C3, y cuando existen dos o más átomos de halógeno o grupos haloalquilo C1-C3, los átomos de halógeno o los grupos haloalquilo C1-C3 pueden ser iguales o diferentes entre sí respectivamente; G representa un átomo de hidrógeno o un grupo de una cualquiera de las siguientes fórmulas:**Fórmula**

Description

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Para el presente compuesto, los compuestos de ciclohexanona de fórmula (I) y (II) pueden formar sales agronómicamente aceptables con bases inorgánicas o bases orgánicas y la presente invención puede abarcar las formas de sal del compuesto de ciclohexanona. La sal incluye por ejemplo, sales que se forman mezclando el compuesto con bases inorgánicas (por ejemplo, hidróxidos, carbonatos, hidrogenocarbonatos, acetatos o hidruros de metales alcalinos (por ejemplo, litio, sodio y potasio)), hidróxidos o hidruros de metales alcalinotérreos (por ejemplo, magnesio, calcio y bario) y amonio), bases orgánicas (por ejemplo, dimetilamina, trietilamina, piperazina, pirrolidina, piperidina, 2-feniletilamina, bencilamina, etanolamina, dietanolamina, piridina y colidina) o alcóxidos metálicos (por ejemplo, metóxido de sodio, terc-butóxido de potasio y metóxido de magnesio).
Cuando el presente compuesto tiene uno o más centros asimétricos, pueden existir dos o más estereoisómeros (por ejemplo, enantiómero y diastereómero). El presente compuesto puede abarcar todos estos estereoisómeros y una mezcla de dos o más estereoisómeros.
Asimismo cuando el presente compuesto contiene isómeros geométricos debido al doble enlace y similares, pueden existir dos o más isómeros geométricos (por ejemplo, cada isómero E/Z o trans/cis, cada isómero S-trans/S-cis y otros). El presente compuesto puede abarcar todos estos isómeros geométricos y una mezcla de dos o más isómeros geométricos arbitrarios.
Como una realización del presente compuesto, están incluidos los presentes compuestos por ejemplo.
un compuesto en donde m es 2;
un compuesto en donde n es 3;
un compuesto en donde m es 2 y n es 3;
un compuesto en donde X es S;
un compuesto en donde R2 es un átomo de hidrógeno;
un compuesto en donde R3 es un átomo de hidrógeno;
un compuesto en donde un radical representado por la fórmula:
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en la fórmula (I) representa -S-CH2CH2-, -S-CH2CH(CH3)-,-S-CH(CH3)CH2-, -O-CH2CH2-, -CH2-CH2CH2-, -S(O)-CH2CH2-, -S(O)-CH2CH(CH3)-, -S(O)2-CH2CH2-, -S(O)2-CH2CH(CH3)-S-CH2C(CH3)2-, -S-CH2C(ciclopropil)-, -SCH2CH(C2H5)-, -S-CH2-, -S-CH2CH2CH2-, -N(CH3)-CH2CH(CH3)-o -N(CH3)-CH2CH2-; un compuesto en donde R4 representa un grupo fenilo, un grupo 2-piridilo, un grupo 3-piridilo, un grupo 4piridilo, un grupo 2-pirimidinilo, un grupo 2-pirazinilo, un grupo 3-piridazinilo o un grupo 3-furilo; un compuesto en donde Z es un grupo fenilo o un grupo alquilo C1-C6 que tiene opcionalmente uno o más átomos de halógeno; un compuesto de ciclohexanona en donde m es un número entero de 1, 2 o 3; n es un número entero de 1, 2 o 3; X representa CH2, O, S, S(O), S(O)2 o N(CH3) ; R1 representa un átomo de hidrógeno; R2 y R3 representan independientemente entre sí un átomo de hidrógeno o un grupo alquilo C1-C6, o R2 y R3 se conectan entre sí para representar una cadena de alquileno C2-C5; R4 representa un grupo arilo C6-C10 o un grupo heteroarilo de cinco a seis miembros (con la condición de que el grupo arilo C6-C10 y el grupo heteroarilo de cinco a seis miembros pueden tener uno o más sustituyentes seleccionados del grupo que consiste en un átomo de halógeno, un grupo ciano, un grupo nitro, un grupo pentafluorotio, un grupo alquilo C1-C6 y un grupo alcoxi C2-C6, y existen dos o más sustituyentes, los sustituyentes pueden ser iguales o diferentes entre sí), y el grupo alquilo C1-C6 y el grupo alcoxi C1-C6 puede tener uno o más átomos de halógeno); G representa un átomo de hidrógeno o un grupo de una cualquiera de las siguientes fórmulas:
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{en donde L representa un átomo de oxígeno; R5 representa un grupo alquilo C1-C6, un grupo alcoxi C2-C6, un grupo (alquenil C3-C6)oxi o un grupo aril(C6C10)oxi; R6 representa un grupo alquilo C1-C6; R7 representa un átomo de hidrógeno; W representa un grupo alcoxi C2-C6} ; Z representa un átomo de halógeno, un grupo fenilo, un grupo alquilo C1-C6, un grupo alquenilo C2-C6, un grupo
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alquinilo C2-C6 o un grupo heteroariloxi de seis miembros (con la condición de que el grupo fenilo y el grupo heteroariloxi de seis miembros pueden tener uno o más sustituyentes seleccionados del grupo que consiste en un átomo de halógeno y un grupo haloalquilo C1-C6, y existen dos o más sustituyentes, los sustituyentes pueden ser iguales o diferentes entre sí)];
[1-1] un compuesto de ciclohexanona de fórmula (I):
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en donde
m es un número entero de 1, 2 o 3; n es un número entero de uno cualquiera de 1 a 5; X representa CH2, O, NR9, S, S(O) o S(O)2; R1 representa un átomo de hidrógeno o un grupo metilo; R2 y R3 representan independientemente entre sí un átomo de hidrógeno, un grupo alquilo C1-C6, un grupo haloalquilo C1-C6, un grupo cicloalquilo C3-C8, un grupo halocicloalquilo C3-C8, un grupo (alquil C1C6)cicloalquilo C3-C8, un grupo (cicloalquil C3-C8)alquilo C1-C6, a (cicloalquil C3-C8)grupo cicloalquilo C3-C8, un grupo (halocicloalquil C3-C8)alquilo C1-C6 o un grupo {(alquil C1-C6)cicloalquil C3-C8}alquilo C1-C6, o R2 y R3 se conectan entre sí para representar una cadena de alquileno C2-C5, o R2 y R3 se combinan entre sí para representar un grupo alquilideno C1-C3 que tiene opcionalmente uno o más átomos de halógeno (con la condición de que cuando m es 2 o 3, dos o tres R2 pueden ser iguales o diferentes entre sí y dos o tres R3 pueden ser iguales o diferentes entre sí); R4 representa un grupo arilo C6-C10 o un grupo heteroarilo de cinco a seis miembros (con la condición de que el grupo arilo C6-C10 y el grupo heteroarilo de cinco a seis miembros pueden tener uno o más sustituyentes seleccionados del grupo que consiste en un átomo de halógeno, un grupo ciano, un grupo nitro, un grupo amino, un grupo (alquil C1-C6)amino, un grupo (alquil C1-C6)(alquil C1-C6)amino, un grupo benzoilamino, un grupo aminocarbonilo, un grupo (alquil C1-C6)aminocarbonilo, un grupo (alquil C1C6)(alquil C1-C6)aminocarbonilo, un grupo pentafluorotio, un grupo alquilo C1-C6, un grupo alquenilo C2-C6, un grupo alquinilo C2-C6, un grupo alcoxi C1-C6, un grupo (alquil C1-C6)tio, un grupo (alquenil C3-C6)oxi, un grupo (alquinil C3-C6)oxi, un grupo arilo C6-C10, un grupo aril(C6-C10)oxi, un grupo (alquil C1-C6)sulfinilo, un grupo alquil(C1-C6)sulfonilo, un grupo hidroxicarbonillo, un grupo (alcoxi C1-C6)carbonilo y un grupo (aril C6C10)alcoxi C1-C6, y cuando existen dos o más sustituyentes, los sustituyentes pueden ser iguales o diferentes entre sí; y el grupo (alquil C1-C6)amino, el grupo (alquil C1-C6)(alquil C1-C6)amino, el grupo benzoilamino, el grupo (alquil C1-C6)aminocarbonilo, el grupo (alquil C1-C6)(alquil C1-C6)aminocarbonilo, el grupo alquilo C1-C6, el grupo alquenilo C2-C6, el grupo alquinillo C2-C6, el grupo alcoxi C1-C6, el grupo (alquil C1-C6)tio, el grupo (alquenil C3-C6)oxi, el grupo (alquinil C3-C6)oxi, el grupo arilo C6-C10, el grupo (aril C6C10)oxi, el grupo (alquil C1-C6)sulfinilo, el grupo (alquil C1-C6)sulfonilo, el grupo (alcoxi C1-C6)carbonilo y el grupo (aril C6-C10)alcoxi C1-C6 pueden tener cada uno uno o más átomos de halógeno, y cuando existen dos o más átomos de halógeno, los átomos de halógeno pueden ser iguales o diferentes entre sí respectivamente); G representa un átomo de hidrógeno o un grupo de una cualquiera de las siguientes fórmulas:
imagen12
{en donde L representa un átomo de oxígeno o un átomo de azufre; R5 representa un grupo alquilo C1-C6, un grupo cicloalquilo C3-C8, un grupo alquenilo C2-C6, un grupo alquinilo C2-C6, un grupo arilo C6-C10, un grupo (aril C6-C10)alquilo C1-C6, un grupo alcoxi C2-C6, un grupo cicloalcoxi C3-C8, un grupo (alquenil C3-C6)oxi, un grupo (alquinil C3-C6)oxi, un grupo aril(C6-C10)oxi, un grupo (aril C6-C10)alcoxi C1-C6, un grupo (alquil C1-C6)(alquil C1-C6)amino, un grupo (alquenil C3-C6)(alquenil C3-C6)amino, un grupo (alquil C1-C6)(aril C6-C10)amino o un grupo heteroarilo de cinco a seis miembros (con la condición de que estos grupos pueden tener cada uno uno o más átomos de halógeno, y cuando existen dos o más átomos de halógeno, los átomos de halógeno pueden ser iguales o diferentes entre sí; y el grupo cicloalquilo C3-C8, el grupo arilo C6-C10, un radical arilo del grupo (aril C6-C10)alquilo C1-C6, un grupo cicloalcoxi C3-C8, un grupo aril(C6-C10)oxi, un radical arilo del grupo (aril C6-C10)alcoxi C1-C6, un radical arilo del grupo (alquil C1-C6)(aril C6-C10)amino y un grupo heteroarilo de cinco a seis miembros pueden tener
11
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triclorfón (abrev. DEP), vamidotión, forato, cadusafos.
(2)
Compuestos de carbamato alanicarb, bendiocarb, benfuracarb, BPMC, carbarilo, carbofurano, carbosulfán, cloetocarb, etiofencarb, fenobucarb, fenotiocarb, fenoxicarb, furatiocarb, isoprocarb (abrev. MIPC), metolcarb, metomilo, metiocarb, oxamilo, pirimicarb, propoxur (abrev. PHC), XMC, tiodicarb, xililcarb, aldicarb.
(3)
Compuestos piretroides acrinatrina, aletrina, beta-ciflutrina, bifentrina, cicloprotrina, ciflutrina, cihalotrina, cipermetrina, empentrina, deltametrina, esfenvalerato, etofenprox, fenpropatrina, fenvalerato, flucitrinato, flufenoprox, flumetrina, fluvalinato, halfenprox, imiprotrina, permetrina, praletrina, piretrinas, resmetrina, sigma-cipermetrina, silafluofeno, teflutrina, tralometrina, transflutrina, tetrametrina, fenotrina, cifenotrina, alfa-cipermetrina, zeta-cipermetrina, lambdacialotrina, gamma-cihalotrina, furametrina, tau-fluvalinato, metoflutrina, proflutrina, dimeflutrina, 2,2dimetil-3-(2-ciano-1-propenil)ciclopropanocarboxilato de 2,3,5,6-tetrafluoro-4-(metoximetil)bencilo, 2,2,3,3tetrametilciclopropanocarboxilato de 2,3,5,6-tetrafluoro-4-(metoximetil)bencilo, protrifenbute.
(4)
Compuestos de toxina nereis cartap, bensultap, tiociclam, monosultap, bisultap.
(5)
Compuestos neonicotinoides imidacloprid, nitenpiram, acetamiprid, tiametoxam, tiacloprid, dinotefurano, clotianidina.
(6)
Compuestos de benzoilureaclorfluazurón, bistriflurón, diflubenzurón, fluazurón, flucicloxurón, flufenoxurón, hexaflumurón, lufenurón, novalurón, noviflumurón, teflubenzurón, triflumurón.
(7)
Compuestos de fenilpirazol acetoprol, etiprol, fipronilo, vaniliprol, piriprol, pirafluprol.
(8)
Toxinas Bt esporas vivas y toxinas cristalinas originadas a partir de Bacillus thuringiensis y una mezcla de los mismos.
(9)
Compuestos de hidrazina cromafenozida, halofenozida, metoxifenozida, tebufenozida.
(10)
Compuestos organoclorados aldrina, dieldrina, clordano, DDT, dienocloro, endosulfán, metoxicloro.
(11)
Otros ingredientes activos de plaguicidas aceite de maquinaria, nicotin-sulfato; avermectina-B, bromopropilato, buprofezina, clorfenapir, ciromazina, DCIP (éter diclorodiisopropílico), D-D (1,3-Dicloropropeno), emamectina-benzoato, fenazaquina, flupirazofos, hidropreno, metopreno, indoxacarb, metoxadiazona, milbemicina-A, pimetrozina, piridalilo, piriproxifeno, espinosad, sulfluramida, tolfenpirad, triazamato, flubendiamida, lepimectina, fosfuro de aluminio, óxido arsenioso, benclotiaz, cianamida cálcica, polisulfuro de calcio, DSP, flonicamida, flurimfeno, formetanato, fosfuro de hidrógeno, metam-amónico, metam-sódico, bromuro de metilo, oleato de potasio, espiromesifeno, sulfoxaflor, azufre, metaflumizona, spirotretramat, pirifluquinazona, espinetoram, clorantraniliprol, tralopirilo, diafentiurón.
Un compuesto de fórmula (A):
imagen18
en donde
Xa1 representa un grupo metilo, un átomo de cloro, un átomo de bromo o un átomo de flúor, Xa2 representa un átomo de flúor, un átomo de cloro, un átomo de bromo, un grupo haloalquilo C1-C4 o un grupo haloalcoxi C1-C4, Xa3 representa un átomo de flúor, un átomo de cloro o un átomo de bromo, Xa4 representa un grupo alquilo C1-C4 opcionalmente sustituido, un grupo alquenilo C3-C4 opcionalmente sustituido, un grupo alquinilo C3-C4 opcionalmente sustituido, un grupo cicloalquilalquilo C3-C5 opcionalmente sustituido o un átomo de hidrógeno, Xa5 representa un átomo de hidrógeno o un grupo metilo, Xa6 representa un átomo de hidrógeno, un átomo de flúor o un átomo de cloro, y Xa7 representa un átomo de hidrógeno, un átomo de flúor o un átomo de cloro.
Un compuesto de fórmula (B):
17
imagen19
en donde
Xb1 representa un grupo Xb2-NH-C(=O), un grupo Xb2-C(=O)-NH-CH2, un grupo Xb3-S(O), un grupo pirrol-1-ilo
5 opcionalmente sustituido, un grupo imidazol-1-ilo opcionalmente sustituido, un grupo pirazol-1-ilo opcionalmente sustituido o un grupo 1,2,4-triazol-1-ilo opcionalmente sustituido, Xb2 representa un grupo haloalquilo C1-C4 opcionalmente sustituido tal como un grupo 2,2,2-trifluoroetilo o un grupo cicloalquilo C3-C6 opcionalmente sustituido tal como un grupo ciclopropilo, Xb3 representa un grupo alquilo C1-C4 opcionalmente sustituido tal como un grupo metilo, y Xb4 representa un átomo de hidrógeno, un átomo de cloro, un grupo ciano o un grupo
10 metilo.
Un compuesto de fórmula (C):
imagen20
15 en donde
XC1 representa un grupo alquilo C1-C4 tal como un tal como un grupo 3,3,3-trifluoropropilo, un grupo alcoxi C1-C4 opcionalmente sustituido tal como un grupo 2,2,2-tricloroetoxi, un grupo fenilo opcionalmente sustituido tal como un grupo 4-cianofenilo o un grupo piridilo opcionalmente sustituido tal como un grupo 2-cloro-3-piridilo, XC2
20 representa un grupo metilo o un grupo trifluorometiltio, y XC3 representa un grupo metilo o un átomo de halógeno.
Los ejemplos del ingrediente activo como miticidas incluyen los siguientes:
25 acequinocilo, amitraz, benzoximato, bifenazato, bromopropilato, quinometionato, clorobenzilato, CPCBS (clorfenson), clofentezina, ciflumetofeno, kelthane (que también es referido como dicofol), etoxazol, óxido de fenbutatina, fenotiocarb, fenpiroximato, fluacripirim, halfenprox, hexitiazox, propargita (abrev. BPPS), polinactinas, piridabeno, pirimidifeno, tebufenpirad, tetradifón, espirodiclofeno, espiromesifeno, espirotetramato, amidoflumet y cienopirafeno.
30 Los ejemplos del ingrediente activo como nematocidas incluyen los siguientes:
DCIP, fostiazato, levamisol, isotiocianato de metilo, tartarato de morantel e imiciafos.
35 Los ejemplos del ingrediente activo como fungicidas incluyen los siguientes:
(1) Compuestos de polihaloalquiltio captan, folpet y otros.
(2) Compuestos organofosforados 40 IBP, EDDP, tolclofos-metilo y otros.
(3)
Compuestos de benzimidazol benomilo, carbendazim, tiofanato-metilo, tiabendazol y otros.
(4)
Compuestos de carboxamida carboxina, mepronilo, flutolanilo, tifluzamid, furametpir, boscalid, pentiopirad y otros.
45 (5) Compuestos de dicarboxiimida procimidona, iprodiona, vinclozolina y otros.
(6) Compuestos de acilalanina metalaxilo y otros.
(7) Compuestos de azol 50 triadimefón, triadimenol, propiconazol, tebuconazol, ciproconazol, epoxiconazol, protioconazol, ipconazol,
18
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(en donde L, R5, R6, R7 y W se definen como antes)
X1 representa un átomo de halógeno (por ejemplo, un átomo de cloro, un átomo de bromo, un átomo de yodo y similares) o un grupo (alquil C1-C3)sulfoniloxi opcionalmente sustituido con uno o más átomos de halógeno (por ejemplo, un grupo metilsulfoniloxi, un grupo trifluorometilsulfoniloxi) o un grupo de fórmula: OG1 (con la condición de que cuando G1 representa un grupo de fórmula:
imagen23,
X1 representa un átomo de halógeno o un grupo (alquil C1-C3)sulfoniloxi opcionalmente sustituido con uno o más átomos de halógeno), R1, R2, R3, R4, X, n, m y Z se definen como antes].
Esta reacción se puede llevar a cabo en un disolvente. Los ejemplos del disolvente que se puede utilizar incluyen hidrocarburos aromáticos tales como benceno y tolueno; éteres tales como éter dietílico, éter diisopropílico, dioxano, tetrahidrofurano y dimetoxietano; hidrocarburos halogenados tales como diclorometano, cloroformo y 1,2dicloroetano; amidas tales como dimetilformamida y dimetilacetamida; sulfóxidos tales como dimetilsulfóxido; sulfonas tales como sulfolano; y mezclas disolventes de los mismos.
Los ejemplos del compuesto de fórmula (4) que se van a utilizar en esta reacción incluyen haluros de ácidos carboxílicos tales como cloruro de acetilo, cloruro de propionilo, cloruro de isobutirilo, cloruro de pivaloilo, cloruro de benzoilo y cloruro de ácido ciclohexanocarboxílico; anhidruros de ácidos carboxílicos tales como anhidruro de ácido acético y anhidruro de ácido trifluoroacético; haluros de semiésteres carbonato tales como cloroformiato de metilo, cloroformiato de etilo y cloroformiato de fenilo; haluros de ácidos carbámicos tales como cloruro de dimetilcarbamoilo; haluros de ácidos sulfónicos tales como cloruro de metanosulfonilo y cloruro de p-toluenosulfonilo; anhidruros de ácidos sulfónicos tales como anhidruro de ácido metanosulfónico y anhidruro de ácido trifluorometanosulfónico; éteres de alquilhalogenoalquilo tales como éter clorometil-metílico y éter clorometil-etílico. La cantidad utilizada del compuesto de fórmula (4) se encuentra usualmente en un intervalo de 1 equivalente molar
o más y preferiblemente dentro de un intervalo de 1 a 3 equivalentes molares de la cantidad del compuesto de fórmula (1a).
Esta reacción se lleva a cabo usualmente en presencia de una base. Los ejemplos de la base que se va a utilizar en esta reacción incluyen bases orgánicas tales como trietilamina, tripropilamina, piridina, dimetilaminopiridina, 1,8diazabiciclo[5,4,0]-7-undeceno; y bases inorgánicas tales como hidróxido de sodio, hidróxido de potasio, hidróxido de calcio, carbonato de sodio, carbonato de potasio, hidrogenocarbonato de sodio, carbonato de calcio e hidruro de sodio. La cantidad utilizada de la base se encuentra usualmente en un intervalo de 0,5 a 10 equivalentes molares y preferiblemente dentro de un intervalo de 1 a 5 equivalentes molares de la cantidad del compuesto de fórmula (1a).
La temperatura de reacción se encuentra usualmente en un intervalo de -30 a 180°C y preferiblemente dentro de un intervalo de -10 a 50°C. El período de reacción de esta reacción se encuentra usualmente en un intervalo de 10 minutos a 30 horas.
La finalización de esta reacción se puede confirmar tomando muestras de una parte de las mezclas de reacción seguido de la realización de medios analíticos tales como cromatografía en capa fina y cromatografía líquida de alta resolución. Cuando se completa esta reacción, por ejemplo, la mezcla de reacción se mezcla con agua y se extrae con un disolvente orgánico y las capas orgánicas resultantes se tratan (por ejemplo, por medio de secado y concentración) para obtener el compuesto de fórmula (1b).
El compuesto de fórmula (4) es un compuesto conocido, o se puede preparar a partir de un compuesto conocido.
Procedimiento 3
El presente compuesto en donde X representa S(O) se puede preparar oxidando el compuesto en donde X representa S. Cuando un grupo alquiltio, un grupo alquilsulfinilo, un grupo haloalquiltio y/o un grupo haloalquilsulfinilo está/están contenidos en cualquier posición distinta de X en el compuesto de fórmula (1c), estos grupos se pueden oxidar.
imagen24
21
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resultantes se tratan (por ejemplo, por medio de secado y concentración) para obtener el compuesto de fórmula (1f). Procedimiento 5 El presente compuesto de fórmula (1a) en donde G representa un átomo de hidrógeno se puede preparar haciendo
reaccionar el compuesto de fórmula (2) y el compuesto de fórmula (31) en presencia de una base.
imagen26
10 [en donde, R1, R2, R3, R4, X, n, m y Z se definen como antes]
La reacción se lleva a cabo usualmente en un disolvente. Los ejemplos del disolvente que se puede utilizar incluyen hidrocarburos aromáticos tales como benceno, tolueno y xileno; éteres tales como éter dietílico, éter diisopropílico, dioxano, tetrahidrofurano y dimetoxietano; hidrocarburos halogenados tales como diclorometano, cloroformo y 1,2
15 dicloroetano; amidas tales como dimetilformamida y dimetilacetamida; sulfonas tales como sulfolano; y mezclas disolventes de los mismos.
Los ejemplos de la base que se va a utilizar en la reacción incluyen bases orgánicas tales como trietilamina, tripropilamina, piridina, dimetilaminopiridina, 1,8-diazabiciclo[5,4,0]-7-undeceno. La cantidad utilizada de la base se 20 encuentra usualmente en un intervalo de 1 a 10 equivalentes molares y preferiblemente dentro de un intervalo de 1 a 5 equivalentes molares de la cantidad del compuesto de fórmula (2). La cantidad utilizada del compuesto de fórmula
(31) se encuentra usualmente en un intervalo de 1 a 3 equivalentes molares de la cantidad del compuesto de fórmula (2).
25 La temperatura de reacción se encuentra usualmente en un intervalo de -60 a 180°C y preferiblemente dentro de un intervalo de -10 a 100°C. El período de reacción de esta reacción se encuentra usualmente en un intervalo de 10 minutos a 30 horas. La finalización de la reacción se puede confirmar analizando una parte de las mezclas de reacción en medios analíticos tales como cromatografía en capa fina y cromatografía líquida de alta resolución. Cuando se completa la reacción, por ejemplo, después de añadir un ácido a las mezclas de reacción, la mezcla de
30 reacción se mezcla con agua y se extrae con un disolvente orgánico y las capas orgánicas resultantes se tratan (por ejemplo, por medio de secado y concentración) para obtener el compuesto de fórmula (1a).
Procedimiento 6
35 El presente compuesto de fórmula (1 g) se puede preparar haciendo reaccionar el compuesto de fórmula (22) y el
imagen27
[en donde G3 representa un grupo de fórmula:
40 (en donde L y R5 se definen como antes), G4 representa un átomo de hidrógeno o un grupo de fórmula: imagen28
imagen29
(en donde L y R5 se definen como antes), y 45 R1, R2, R3, R9, n, m y Z se definen como antes]
La reacción se lleva a cabo usualmente en un disolvente. Los ejemplos del disolvente incluyen éteres tales como éter dietílico, éter diisopropílico, dioxano, tetrahidrofurano y dimetoxietano; hidrocarburos halogenados tales como
23
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