ES2349257T3 - BENZOILCICLOHEXENONAS REPLACED AND ITS USE AS HERBICITY AGENTS. - Google Patents
BENZOILCICLOHEXENONAS REPLACED AND ITS USE AS HERBICITY AGENTS. Download PDFInfo
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- ES2349257T3 ES2349257T3 ES02730231T ES02730231T ES2349257T3 ES 2349257 T3 ES2349257 T3 ES 2349257T3 ES 02730231 T ES02730231 T ES 02730231T ES 02730231 T ES02730231 T ES 02730231T ES 2349257 T3 ES2349257 T3 ES 2349257T3
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- fluoro
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
Compuestos de la fórmula (I) 5 en la que Q representa O (oxígeno) o S (azufre), R1 representa hidrógeno, fluoro, cloro o bromo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, eventualmente sustituido en cada caso con fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, 10 etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, o representa fenilo. R2 representa hidrógeno, fluoro, cloro o bromo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, eventualmente sustituido en cada caso con fluoro o cloro, o eventualmente también en común con R1 representa O (oxígeno), etano-1,2-diílo, 15 propano-1,3-diílo o butano-1,4-diílo, R3 representa hidrógeno, nitro, ciano, carboxi, carbamoílo, tiocarbamoílo, fluoro, cloro, bromo, yodo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butiltio, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, 20 etilsulfonilo, n- o i-propilsulfonilo, en cada caso eventualmente sustituido con fluoro, cloro, metoxi, etoxi, metiltio, etiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, o representa metilamino, etilamino, n- o i-propilamino, n-, i-, s- o t-butilamino, dimetilamino, dietilamino, dimetilaminocarbonilo, dietilaminocarbonilo, dimetilaminosulfonilo o dietilaminosulfonilo. 25 R4 representa hidrógeno, nitro, ciano, carboxi, carbamoílo, tiocarbamoílo, fluoro, cloro, bromo, yodo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butiltio, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, n- o i-propilsulfonilo, en cada caso eventualmente sustituido con 5 fluoro, cloro, metoxi, etoxi, metiltio, etiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, o representa metilamino, etilamino, n- o i-propilamino, n-, i-, s- o t-butilamino, dimetilamino, dietilamino, dimetilaminocarbonilo, dietilaminocarbonilo, dimetilaminosulfonilo o dietilaminosulfonilo. R5 representa hidrógeno, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, n-, 10 i-, s- o t-pentilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, metilamino, etilamino, n- o i-propilamino, n -, i-, s- o t-butilamino, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metoxi, etoxi, n- o i-propoxi, representa dimetilamino o dietilamino, representa 15 etenilo, propenilo, butenilo, pentenilo, etinilo, propinilo, butinilo o pentinilo, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo o ciclohexilmetilo, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metilo o etilo, o representa fenilo, feniltio, fenilsulfinilo, 20 fenilsulfonilo, naftilo, fenilmetilo, feniletilo, naftilmetilo o naftiletilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi o trifluorometoxi, o representa la agrupación -C(Q)-Z. Y representa hidroxi, formiloxi, fluoro, cloro o bromo, representa metoxi, etoxi, n- o i-25 propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo etilsulfonilo, acetiloxi, propioniloxi, n- o i-butiroíloxi, metoxicarboniloxi, etoxicarboniloxi, n- o i-propoxicarboniloxi, metilaminocarboniloxi, etilamino-carboniloxi, n- o i- propilaminocarboniloxi, metilsulfoniloxi, etilsulfoniloxi, n- o i- propilsulfoniloxi, en cada caso eventualmente sustituido con ciano, fluoro, cloro, 30 metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, representa propeniloxi, buteniloxi, propiniloxi o butiniloxi, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, o representa feniloxi, feniltio, fenilsulfinilo, fenilsulfonilo, fenilcarboniloxi, fenilcarbonilmetoxi, fenilsulfoniloxi, fenilmetoxi, fenilmetiltio, fenilmetilsulfinilo o 35 fenilmetilsulfonilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metilsulfinilo, etilsulfinilo, trifluorometilsulfinilo, metilsulfonilo, etilsulfonilo o trifluorometilsulfonilo. 5 Z representa hidrógeno, amino, cianoamino, nitroamino, hidroxiamino, hidrazino, representa metilo sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo o etilsulfonilo, representa etenilo, propenilo, butenilo, pentenilo, etinilo, propinilo, butinilo, pentinilo, propeniloxi, buteniloxi, penteniloxi, propeniltio, buteniltio, penteniltio, 10 propenilamino, butenilamino, pentenilamino, propeniloxiamino, buteniloxiamino, penteniloxiamino, etinilo, propinilo, butinilo, pentinilo, propiniloxi, butiniloxi, pentiniloxi, propinilamino, butinilamino o pentinilamino, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, 15 ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilamino, ciclobutilamino, ciclopentilamino, ciclohexilamino, ciclopropilhidrazino, ciclobutilhidrazino, ciclopentilhidrazino, ciclohexilhidrazino, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, ciclopentilmetoxi, ciclohexilmetoxi, ciclopropilmetilamino, ciclobutilmetilamino, 20 ciclopentilmetilamino o ciclohexilmetilamino, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metilo o etilo, representa fenilo, fenilcarbonilo, fenoxi, fenoxicarbonilo, feniltio, fenilamino, fenilhidrazino, naftilo, naftiloxi, naftiltio, naftilamino, fenilmetilo, feniletilo, fenilmetoxi, feniletoxi, fenilmetiltio, feniletiltio, fenilmetilamino, feniletilamino, 25 naftilmetilo, naftiletilo, naftilmetoxi, naftiletoxi, naftilmetilamino o naftiletilamino, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, o 30 representa heterociclilo, heterocicliloxi, heterociclilamino, la agrupación & 8211;N=(heterociclilo), heterociclilalquilo, heterociclilalcoxi o heterociclilalquilamino monocíclico/a o bicíclico/a, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, difluorometilo, trifluorometilo, diclorometilo, triclorometilo, clorodifluorometilo, 35 fluorodiclorometilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, difluorometiltio, trifluorometiltio, metoxicarbonilo, etoxicarbonilo, n- o i-propoxi-carbonilo, tomado de la serie de furilo, tetrahidrofurilo, furiloxi, tetrahidrofuriloxi, furilamino, tetrahidrofurilamino, furilmetilo, tetrahidrofurilmetilo, furilmetoxi, 5 tetrahidrofurilmetoxi, furilmetilamino, tetrahidrofurilmetilamino, dioxolanilo, dioxolanilmetilo, dioxolanilmetoxi, dioxolanilmetilamino, tienilo, tienilamino, tienilmetilo, tienilmetilamino, ditiolanilo, ditiolanilmetilo, ditiolanilmetoxi, ditiolanilmetilamino, pirrolidinilo, pirrolidinilamino, oxopirrolidinilo, pirrolilo, indolilo, pirrolilmetilo, pirazolilo, pirazoliloxi, pirazolilamino, pirazolilmetilo, imidazolilo, 10 imidazolinilo, imidazolilmetilo, imidazolinilmetilo, oxoimidazolinilo, 2-oxo-1,3-diaza-ciclopentilo, oxazolilo, oxazolilamino, dihidrooxazolilo (oxazolinilo), tetrahidrooxazolilo (oxazolidinilo), isoxazolilo, isoxazolilamino, dihidroisoxazolilo (isoxazolinilo), tetrahidroisoxazolilo (isoxazolidinilo), tetrahidro-(2H)-1,2-oxazin-2-ilo, oxazolilmetilo, tiazolilo, tiazolilamino, tiazolilmetilo, dihidrotiazolilo (tiazolinilo), 15 tetrahidrotiazolilo (tiazolidinilo), tiazolimino, tiazoliniltio, tiazolinilamino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, triazolilamino, oxotriazolinilo, tioxotriazolinilo, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolilmetilo, dioxanilo, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, ditianilo, ditianilmetilo, ditianilmetoxi, ditianilmetilamino, piperidinilo, 20 piperidinilamino, oxopiperidinilo, 2-oxo-1,3-diaza-ciclohexilo, 2-oxo-1-aza-cicloheptilo, 2-oxo-1,3-diaza-cicloheptilo, morfolinilo, morfolinilamino, piperazinilo, piridinilo, piridiniloxi, piridiniltio, piridinilamino, 2-(1H)-piridinimino, piridinilmetilo, piridinilmetoxi, pirimidinilo, pirimidiniloxi, pirimidiniltio, pirimidinilamino, pirimidinilmetilo o pirimidinilmetoxi, 25 incluyendo todas las posibles formas tautómeras de los compuestos de la fórmula general (I) y de las posibles sales de los compuestos de la fórmula general (I)Compounds of the formula (I) in which Q represents O (oxygen) or S (sulfur), R1 represents hydrogen, fluoro, chloro or bromine, represents methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, optionally substituted in each case with fluoro, chloro, methoxy, ethoxy, n- or i -propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or represents phenyl. R2 represents hydrogen, fluoro, chloro or bromo, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted in each case with fluoro or chloro, or possibly also in common with R1 represents O (oxygen), ethane-1,2-diyl, propane-1,3-diyl or butane-1,4-diyl, R3 represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro , bromine, iodine, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butylthio, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl , in each case eventually substituted with fluoro, chloro, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t -butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylamino carbonyl, dimethylaminosulfonyl or diethylaminosulfonyl. R4 represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, iodo, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butylthio, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, in each case optionally substituted with 5 fluoro, chloro, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or methylsulfonyl, or methylsulfonyl, or methylsulphonylamino , n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl. R5 represents hydrogen, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, 10 i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i- propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, in each case eventually substituted with cyano, fluoro, chloro, bromo, methoxy, ethoxy, n- or i-propoxy, represents dimethylamino or diethylamino, represents ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentinyl, in each case optionally substituted with fluoro, chloro and / or bromine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case possibly substituted with cyano, fluoro, chloro, bromo, methyl or ethyl, or represents phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, naphthyl, fe nylmethyl, phenylethyl, naphthylmethyl or naphthylethyl, in each case eventually substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, or represents the group -C (Q) -Z. Y represents hydroxy, formyloxy, fluoro, chloro or bromo, represents methoxy, ethoxy, n- or i-25 propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl ethylsulfonyl, acetyloxy, propionyloxy, n- o i-butyloyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulphonyloxy, n- or i-propylsulfonyloxy, in each case, chloro substituted, in each case , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, represents propenyloxy, butenyloxy, propynyloxy or butynyloxy, in each case eventually substituted by fluoro, and / or bromine, or represents phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl, if any s Used with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy , trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl. 5 Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, represents methyl substituted with cyano, fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl or ethyl sulfonyl , represents ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentinyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, 10 propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentyloxy, pentyloxy, pentenyl , propynyloxy, butynyloxy, pentynyloxy, propylamino, butylamino or pentinylamino, in each case eventually substituted with fluoro, chloro and / or bromine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino , cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl or, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case eventually substituted with cyano, fluoro, methyl or chloro, phenyl, bromo phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino, 25 naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy, naphthylmethylamino or naftiletilamino, in each case optionally substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents heterocyclyl, heterocyclyloxy, heterocyclylamino, grouping &8211; N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino monocyclic / a or bicyclic / a, in each case eventually substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy , trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, taken from the furyl series , tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahidrofurilamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, 5 tetrahidrofurilmetoxi, furylmethylamino, tetrahidrofurilmetilamino, dioxolanyl, dioxolanylmethyl, dioxolanilmetoxi, dioxolanilmetilamino, thienyl, thienylamino, thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanyl methyl, ditiolanilmetoxi, ditiolanilmetilamino, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl 10, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinilo, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl , oxazolylamino, dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, isoxazolylamino, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), tetrahydro- (2H) -1,2-oxazolyl-tiazoyl-tiazoylazoyl-tiazoylazoyl-tiazoyl-tiazoylazoyl-tiazoylazoyl-thiazoyl-thiazoyl-thiazoyl-tiazoylamino-thiazoylamino-thiazoylamino-thiazoylamino-thiazoylamino-thiazoyl-thiazoyl-ethylazyl-thiazoyl-ethylazyl group , dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl 15 (thiazolidinyl), tiazolimino, tiazoliniltio, tiazolinilamino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, triazolilamino, oxotriazolinilo, tioxotriazolinilo, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolylmethyl, dioxanyl, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, dithianyl, ditianilmeti lo, dithianylmethoxy, dithianylmethylamino, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinyl amino , piperazinyl, pyridinyl, pyridinyloxy, pyridinylthio, pyridinylamino, 2- (1 H) -pyridinimino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylthio, pyrimidinylamino, pyrimidinylmethyl, or all possible forms of the formula (including pyrimidinyl) I) and of the possible salts of the compounds of the general formula (I)
Description
El invento se refiere a nuevas benzoílciclohexenonas sustituidas, a procedimientos para su preparación y a su utilización como herbicidas. The invention relates to new substituted benzoylcyclohexenones, processes for their preparation and their use as herbicides.
Ya es conocido que determinadas benzoílciclohexenonas o 5 benzoílciclohexanodionas sustituidas, tales como p.ej. los compuestos N-[2,6-dicloro-3-[(3,3-dimetil-2,6-dioxo-ciclohexil)-carbonil]-fenil]-acetamida, N-[2-cloro-3-[(2,6-dioxo-ciclohexil)-carbonil]-4-nitro-fenil]-acetamida, N-[2-cloro-3-[(2,6-dioxo-ciclohexil)-carbonil]-fenil]-acetamida, N-[2,6-dicloro-3-[(2,6-dioxo-ciclohexil)-carbonil]-fenil]-acetamida (compárese el documento de patente de los EE.UU. US-A-4 780 127), presentan 10 propiedades herbicidas (compárense también los documentos de solicitudes de patentes europeas EP-A-090 262, EP-A-135 191, EP-A-137 963, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, y los documentos de solicitudes de patentes internacionales WO-A-96/26200, WO-A-97/46530, WO-A-99/07688, WO-A-99/10327, WO-A-00/05221, WO-A-00/21924). Sin embargo, el efecto de estos compuestos no es 15 satisfactorio en todas las cuestiones. It is already known that certain benzoylcyclohexenones or substituted benzoylcyclohexanediones, such as, for example, the compounds N- [2,6-dichloro-3 - [(3,3-dimethyl-2,6-dioxo-cyclohexyl) -carbonyl] - phenyl] -acetamide, N- [2-chloro-3 - [(2,6-dioxo-cyclohexyl) -carbonyl] -4-nitro-phenyl] -acetamide, N- [2-chloro-3 - [(2, 6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide, N- [2,6-dichloro-3 - [(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide (compare patent document US-A-4 780 127), have 10 herbicidal properties (also compare European patent application documents EP-A-090 262, EP-A-135 191, EP-A-137 963, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, and international patent application documents WO-A-96/26200, WO-A-97 / 46530, WO-A-99/07688, WO-A-99/10327, WO-A-00/05221, WO-A-00/21924). However, the effect of these compounds is not satisfactory in all matters.
Fue misión del presente invento la puesta a disposición de otros herbicidas adicionales. It was the mission of the present invention to make other additional herbicides available.
Se encontraron por fin las nuevas benzoílciclohexenonas sustituidas de la fórmula general (I) 20 The new substituted benzoylcyclohexenones of the general formula (I) were finally found.
en la que in which
Q representa O (oxígeno) o S (azufre), Q represents O (oxygen) or S (sulfur),
R1 representa hidrógeno, fluoro, cloro o bromo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, eventualmente sustituido en cada caso con fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, o representa fenilo. 5 R1 represents hydrogen, fluoro, chloro or bromo, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, optionally substituted in each case with fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or It represents phenyl. 5
R2 representa hidrógeno, fluoro, cloro o bromo, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, eventualmente sustituido en cada caso con fluoro o cloro, o eventualmente también en común con R1 representa O (oxígeno), etano-1,2-diílo, propano-1,3-diilo o butano-1,4-diílo, R2 represents hydrogen, fluoro, chloro or bromo, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted in each case with fluoro or chloro, or possibly also in common with R 1 represents O (oxygen), ethane-1,2-diyl, propane-1,3-diyl or butane-1,4-diyl,
R3, R4 representan, independientemente uno de otro, hidrógeno, nitro, ciano, carboxi, 10 carbamoílo, tiocarbamoílo, fluoro, cloro, bromo, yodo, representan metilo, etilo, n- o i-propilo, n-, i-, s- o t-butiltio, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, n- o i-propilsulfonilo, en cada caso eventualmente sustituido con fluoro, cloro, metoxi, etoxi, metiltio, etiltio, 15 metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, representan metilamino, etilamino, n- o i-propilamino, n-, i-, s- o t-butilamino, dimetilamino, dietilamino, dimetilaminocarbonilo, dietilaminocarbonilo, dimetilaminosulfonilo o dietilaminosulfonilo. R3, R4 represent, independently of one another, hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, iodo, represent methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butylthio, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, in each case optionally substituted with fluoro, chloro, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, methylsulfinon, methylsulfinon, or ethylsulfonyl, represent methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl.
R5 representa hidrógeno, representa metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, n-, 20 i-, s- o t-pentilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, metilamino, etilamino, n- o i-propilamino, n -, i-, s- o t-butilamino, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metoxi, etoxi, n- o i-propoxi, representa dimetilamino o dietilamino, representa 25 etenilo, propenilo, butenilo, pentenilo, etinilo, propinilo, butinilo o pentinilo, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo o ciclohexilmetilo, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metilo o etilo, o representa fenilo, feniltio, fenilsulfinilo, 30 fenilsulfonilo, naftilo, fenilmetilo, feniletilo, naftilmetilo o naftiletilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi o trifluorometoxi, o representa la agrupación -C(Q)-Z. R5 represents hydrogen, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, 20 i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i- propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, in each case eventually substituted with cyano, fluoro, chloro, bromo, methoxy, ethoxy, n- or i-propoxy, represents dimethylamino or diethylamino, represents ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentinyl, in each case optionally substituted with fluoro, chloro and / or bromine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case possibly substituted with cyano, fluoro, chloro, bromo, methyl or ethyl, or represents phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, naphthyl, f enylmethyl, phenylethyl, naphthylmethyl or naphthylethyl, in each case eventually substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, or represents the group -C (Q) -Z.
Y representa hidroxi, formiloxi, fluoro, cloro o bromo, representa metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo etilsulfonilo, acetiloxi, propioniloxi, n- o i-butiroíloxi, metoxicarboniloxi, etoxicarboniloxi, n- o i-propoxicarboniloxi, metilaminocarboniloxi, etilaminocarboniloxi, n- o i-propilaminocarboniloxi, metilsulfoniloxi, etilsulfoniloxi, n- 5 o i-propilsulfoniloxi, en cada caso eventualmente sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo o etilsulfonilo, representa propeniloxi, buteniloxi, propiniloxi o butiniloxi, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, o representa feniloxi, feniltio, fenilsulfinilo, fenilsulfonilo, fenilcarboniloxi, 10 fenilcarbonilmetoxi, fenilsulfoniloxi, fenilmetoxi, fenilmetiltio, fenilmetilsulfinilo o fenilmetilsulfonilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metilsulfinilo, etilsulfinilo, trifluorometilsulfinilo, 15 metilsulfonilo, etilsulfonilo o trifluorometilsulfonilo. Y represents hydroxy, formyloxy, fluoro, chloro or bromo, represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl ethylsulfonyl, acetyloxy, propionyloxy, n- or i -butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulphonyloxy, n-5 or i-propylsulfonyloxy, with each case, if any, , ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, represents propenyloxy, butenyloxy, propynyloxy or butynyloxy, in each case eventually substituted with fluoro, chloro / o bromine, or represents phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl, in each case eventually substituted gone with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy , trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl.
Z representa hidrógeno, amino, cianoamino, nitroamino, hidroxiamino, hidrazino, Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino,
representa metilo sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo o etilsulfonilo, represents methyl substituted with cyano, fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl or ethylsulfonyl,
representa etenilo, propenilo, butenilo, pentenilo, etinilo, propinilo, butinilo, 20 pentinilo, propeniloxi, buteniloxi, penteniloxi, propeniltio, buteniltio, penteniltio, propenilamino, butenilamino, pentenilamino, propeniloxiamino, buteniloxiamino, penteniloxiamino, etinilo, propinilo, butinilo, pentinilo, propiniloxi, butiniloxi, pentiniloxi, propinilamino, butinilamino o pentinilamino, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, 25 represents ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentinyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentyloxy, pentenyl propynyloxy, butyloxy, pentynyloxy, propylamino, butylamino or pentylamino, in each case eventually substituted with fluoro, chloro and / or bromo,
representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilamino, ciclobutilamino, ciclopentilamino, ciclohexilamino, ciclopropilhidrazino, ciclobutilhidrazino, ciclopentilhidrazino, ciclohexilhidrazino, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, 30 ciclopentilmetoxi, ciclohexilmetoxi, ciclopropilmetilamino, ciclobutilmetilamino, ciclopentilmetilamino o ciclohexilmetilamino, en cada caso eventualmente sustituido con ciano, fluoro, cloro, bromo, metilo o etilo, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, ciclopropilhidrazino, ciclobutilhidrazino, ciclopentilhidrazino, ciclohexilhidrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, 30 cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case eventually substituted with cyano, fluoro, chloro, bromo, methyl or ethyl,
fenilo, fenilcarbonilo, fenoxi, fenoxicarbonilo, feniltio, fenilamino, fenilhidrazino, naftilo, naftiloxi, naftiltio, naftilamino, fenilmetilo, feniletilo, fenilmetoxi, feniletoxi, 35 phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, 35
fenilmetiltio, feniletiltio, fenilmetilamino, feniletilamino, naftilmetilo, naftiletilo, naftilmetoxi, naftiletoxi, naftilmetilamino o naftiletilamino, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metoxicarbonilo, etoxicarbonilo, n- o i-5 propoxicabonilo, o phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy, naphthylmethylamino or naphthylethylamino, in each case eventually substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-5 propoxycarbonyl, or
representa heterociclilo, heterocicliloxi, heterociclilamino, la agrupación –N=(heterociclilo), heterociclilalquilo, heterociclilalcoxi o heterociclilalquilamino monocíclico/a o bicíclico/a, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, 10 difluorometilo, trifluorometilo, diclorometilo, triclorometilo, clorodifluorometilo, fluorodiclorometilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, n-, i-, s- o t-butiltio, difluorometiltio, trifluorometiltio, metoxicarbonilo, etoxicarbonilo, n- o i-propoxi-carbonilo, tomado de la serie de furilo, tetrahidrofurilo, furiloxi, tetrahidrofuriloxi, furilamino, 15 tetrahidrofurilamino, furilmetilo, tetrahidrofurilmetilo, furilmetoxi, tetrahidrofurilmetoxi, furilmetilamino, tetrahidrofurilmetilamino, dioxolanilo, dioxolanilmetilo, dioxolanilmetoxi, dioxolanilmetilamino, tienilo, tienilamino, tienilmetilo, tienilmetilamino, ditiolanilo, ditiolanilmetilo, ditiolanilmetoxi, ditiolanilmetilamino, pirrolidinilo, pirrolidinilamino, oxopirrolidinilo, pirrolilo, indolilo, 20 pirrolilmetilo, pirazolilo, pirazoliloxi, pirazolilamino, pirazolilmetilo, imidazolilo, imidazolinilo, imidazolilmetilo, imidazolinilmetilo, oxoimidazolinilo, 2-oxo-1,3-diaza-ciclopentilo, oxazolilo, oxazolilamino, dihidrooxazolilo (oxazolinilo), tetrahidrooxazolilo (oxazolidinilo), isoxazolilo, isoxazolilamino, dihidroisoxazolilo (isoxazolinilo), tetrahidroisoxazolilo (isoxazolidinilo), tetrahidro-(2H)-1,2-oxazin-2-25 ilo, oxazolilmetilo, tiazolilo, tiazolilamino, tiazolilmetilo, dihidrotiazolilo (tiazolinilo), tetrahidrotiazolilo (tiazolidinilo), tiazolimino, tiazoliniltio, tiazolinilamino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, triazolilamino, oxotriazolinilo, tioxotriazolinilo, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolilmetilo, dioxanilo, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, 30 ditianilo, ditianilmetilo, ditianilmetoxi, ditianilmetilamino, piperidinilo, piperidinilamino, oxopiperidinilo, 2-oxo-1,3-diaza-ciclohexilo, 2-oxo-1-aza-cicloheptilo, 2-oxo-1,3-diaza-cicloheptilo, morfolinilo, morfolinilamino, piperazinilo, piridinilo, piridiniloxi, piridiniltio, piridinilamino, 2-(1H)-piridinimino, piridinilmetilo, represents heterocyclyl, heterocyclyloxy, heterocyclylamino, the grouping –N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclyl alkylamino monocyclic / a or bicyclic / a, in each case eventually substituted with nitro, cyano, fluoro, methyl, bromo, ethyl, bromo or i-propyl, n-, i-, s- or t-butyl, 10 difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl taken from the series of furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl, dioxolanylmethyl, dioxolanylmethyl, dioxolanylmethyl, dioxolanylmethyl, dioxolanylmethyl yl, thienylamino, thienylmethyl, thienylmethylamino, dithiolanyl, ditiolanilmetilo, ditiolanilmetoxi, ditiolanilmetilamino, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, 20 pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinilo, 2-oxo -1,3-diaza-cyclopentyl, oxazolyl, oxazolylamino, dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, isoxazolylamino, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), tetrahydro-2-az) -25 yl, oxazolylmethyl, thiazolyl, thiazolylamino, thiazolylmethyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), tiazolimino, tiazoliniltio, tiazolinilamino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, triazolilamino, oxotriazolinilo, tioxotriazolinilo, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolylmethyl, dioxanyl, gave oxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, dithianyl, dithianylmethyl, dithianylmethoxy, dithianylmethylamino, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-1-aza-1,3-aza -diaza-cycloheptyl, morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylthio, pyridinylamino, 2- (1 H) -pyridinimino, pyridinylmethyl,
piridinilmetoxi, pirimidinilo, pirimidiniloxi, pirimidiniltio, pirimidinilamino, pirimidinilmetilo o pirimidinilmetoxi, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylthio, pyrimidinylamino, pyrimidinylmethyl or pyrimidinylmethoxy,
incluyendo todas las formas tautómeras posibles de los compuestos de la fórmula general (I) y de las sales posibles de los compuestos de la fórmula general (I). including all possible tautomeric forms of the compounds of the general formula (I) and of the possible salts of the compounds of the general formula (I).
R1 de manera muy especialmente preferida, representa hidrógeno, representa metilo, 5 etilo, n- o i-propilo, metiltio, etiltio, n- o i-propiltio, en cada caso eventualmente sustituido con fluoro o cloro, o representa fenilo. R1 very particularly preferably, represents hydrogen, represents methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, in each case eventually substituted with fluoro or chloro, or represents phenyl.
R2 de manera muy especialmente preferida, representa hidrógeno, representa metilo, etilo, n- o i-propilo, en cada caso eventualmente sustituido con fluoro o cloro, o eventualmente también en común con R1 representa etano-1,2-diílo, propano-1,3-10 diílo o butano-1,4-diílo. R2 most particularly preferably represents hydrogen, represents methyl, ethyl, n- or i-propyl, in each case eventually substituted with fluoro or chloro, or possibly also in common with R1 represents ethane-1,2-diyl, propane- 1,3-10 diyl or butane-1,4-diyl.
R3, R4 de manera muy especialmente preferida, representan, independientemente unos de otros, hidrógeno, nitro, ciano, fluoro, cloro, bromo, yodo, metilo, etilo, n- o i-propilo, difluorometilo, trifluorometilo, diclorometilo, triclorometilo, metoximetilo, metiltiometilo, metilsulfinilmetilo, metilsulfonilmetilo, metoxi, etoxi, difluorometoxi, 15 trifluorometoxi, metiltio, etiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo, etilsulfonilo o dimetilaminosulfonilo. R3, R4 very particularly preferably, independently represent one another, hydrogen, nitro, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl , methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
R5 de manera muy especialmente preferida, representa hidrógeno, representa metilo, etilo, n- o i-propilo, n- o i-butilo, en cada caso eventualmente sustituido con ciano, fluoro, cloro, metoxi o etoxi, representa metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, 20 n- o i-propiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, metilamino, etilamino, n- o i-propilamino o dimetilamino, representa propenilo, butenilo, propinilo o butinilo, en cada caso eventualmente sustituido con fluoro y/o cloro, representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo o ciclohexilmetilo, en cada caso 25 eventualmente sustituido con ciano, fluoro, cloro o metilo, o representa fenilo, feniltio, fenilsulfinilo, fenilsulfonilo, fenilmetilo o feniletilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi o trifluorometoxi, o representa la agrupación -C(Q)-Z. 30 R5 very particularly preferably, represents hydrogen, represents methyl, ethyl, n- or i-propyl, n- or i-butyl, in each case eventually substituted with cyano, fluoro, chloro, methoxy or ethoxy, represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, 20 n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, represents propenyl, Butenyl, propynyl or butynyl, in each case optionally substituted with fluoro and / or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case eventually substituted with cyano, fluoro, chloro or methyl, or represents phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl, in each case eventually substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, met oxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, or represents the group -C (Q) -Z. 30
Y de manera muy especialmente preferida, representa hidroxi, representa metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo, etilsulfonilo, acetiloxi, propioniloxi, n- o i-butiroíloxi, metoxicarboniloxi, etoxicarboniloxi, n- o i-propoxicarboniloxi, metilaminocarboniloxi, etilaminocarboniloxi, n- o i-propilaminocarboniloxi, 35 And most particularly preferably, it represents hydroxy, represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i- butyloyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, 35
metilsulfoniloxi, etilsulfoniloxi, n- o i-propilsulfoniloxi, en cada caso eventualmente sustituido con fluoro y/o cloro, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, in each case eventually substituted with fluoro and / or chloro,
representa propeniloxi, buteniloxi, propiniloxi o butiniloxi, en cada caso eventualmente sustituido con fluoro, cloro y/o bromo, o represents propenyloxy, butenyloxy, propynyloxy or butyloxy, in each case optionally substituted with fluoro, chloro and / or bromo, or
representa feniloxi, feniltio, fenilsulfinilo, fenilsulfonilo, fenilcarboniloxi, 5 fenilcarbonilmetoxi, fenilsulfoniloxi, fenilmetoxi, fenilmetiltio, fenilmetilsulfinilo o fenilmetilsulfonilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metilsulfinilo, etilsulfinilo, trifluorometilsulfinilo, 10 metilsulfonilo, etilsulfonilo o trifluorometilsulfonilo. represents phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonymethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl, in each case optionally substituted with nitro, cyano, fluoro, methyl, chloro, methyl or methyl , n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulphinyl trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl.
Z de manera muy especialmente preferida, representa amino, cianoamino, hidrazino, Z very particularly preferably, represents amino, cyanoamino, hydrazino,
representa metilo sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, 15 metilsulfonilo o etilsulfonilo, represents methyl substituted with cyano, fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl,
representa etilo, n- o i-propilo, n-, i-, s- o t-butilo, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilamino, etilamino, n- o i-propilamino, metoxiamino, etoxiamino, n- o i-propoxiamino, metilhidrazino, etilhidrazino, n- o i-propilhidrazino, n-, i-, s- o t-butilhidrazino, dimetilamino, N-metil-metoxiamino o 20 dimetilhidrazino, en cada caso eventualmente sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo o etilsulfonilo, represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n - or i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, dimethylamino, N-methyl-methoxyamino or dimethylhydrazino, in each case optionally substituted with cyano, fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethyl sulfonyl ,
representa etenilo, propenilo, butenilo, etinilo, propinilo, butinilo, propeniloxi, buteniloxi, propeniltio, buteniltio, propenilamino, butenilamino, propeniloxiamino, 25 buteniloxiamino, etinilo, propinilo, butinilo, propiniloxi, butiniloxi, propinilamino o butinilamino, en cada caso eventualmente sustituido con fluoro y/o cloro, represents ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, propenyloxyamino, butenyloxyamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, optionally substituted or butylated in each case fluoro and / or chlorine,
representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilamino, ciclobutilamino, ciclopentilamino, ciclohexilamino, ciclopentilhidrazino, ciclohexilhidrazino, 30 ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, ciclopentilmetoxi, ciclohexilmetoxi, ciclopropilmetilamino, ciclobutilmetilamino, ciclopentilmetilamino o ciclohexilmetilamino, en cada caso eventualmente sustituido con ciano, fluoro, cloro o metilo, 35 represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, ciclopentilhidrazino, ciclohexilhidrazino, 30 cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case possibly substituted with cyano, fluoro, chloro or methyl,
representa fenilo, fenilcarbonilo, fenoxi, fenoxicarbonilo, feniltio, fenilamino, fenilhidrazino, fenilmetilo, feniletilo, fenilmetoxi, feniletoxi, fenilmetiltio, feniletiltio, fenilmetilamino o feniletilamino, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, 5 metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, represents phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino or phenylethylamino, in each case eventually substituted with nitro, cyano, fluoro, chloro, methyl, chloro, methyl , n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
o representa heterociclilo, heterocicliloxi, heterociclilamino, la agrupación -N=(heterociclilo), heterociclilalquilo, heterociclilalcoxi o heterociclilalquilamino monocíclico/a o bicíclico/a, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, 10 difluorometilo, trifluorometilo, diclorometilo, triclorometilo, clorodifluorometilo, fluorodiclorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, tomado de la serie de furilo, tetrahidrofurilo, furiloxi, tetrahidrofuriloxi, furilamino, tetrahidrofurilamino, furilmetilo, 15 tetrahidrofurilmetilo, furilmetoxi, tetrahidrofurilmetoxi, furilmetilamino, tetrahidrofurilmetilamino, dioxolanilo, dioxolanilmetilo, dioxolanilmetoxi, dioxolanilmetilamino, tienilo, tienilmetilo, ditiolanilo, ditiolanilmetilo, ditiolanilmetoxi, ditiolanilmetilamino, pirrolidinilo, pirrolidinilamino, oxopirrolidinilo, pirrolilo, indolilo, pirrolilmetilo, pirazolilo, pirazoliloxi, pirazolilamino, pirazolilmetilo, imidazolilo, 20 imidazolinilo, imidazolilmetilo, imidazolinilmetilo, oxoimidazolinilo, 2-oxo-1,3-diaza-ciclopentilo, oxazolilo, oxazolilmetilo, dihidrooxazolilo (oxazolinilo), tetrahidrooxazolilo (oxazolidinilo), isoxazolilo, dihidroisoxazolilo (isoxazolinilo), tetrahidro-(2H)-1,2-oxazin-2-ilo, tetrahidroisoxazolilo (isoxazolidinilo), tiazolilo, tiazolilmetilo, dihidrotiazolilo (tiazolinilo), tetrahidrotiazolilo (tiazolidinilo), 25 tiazolimino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, oxotriazolinilo, oxatetrazolinilmetilo, tetrazolilmetilo, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolilmetilo, dioxanilo, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, ditianilo, ditianilmetilo, ditianilmetoxi, ditianilmetilamino, triazolilamino, piperidinilo, piperidinilamino, 2-(1H)-piridinimino, 30 oxopiperidinilo, 2-oxo-1,3-diaza-ciclohexilo, 2-oxo-1-aza-cicloheptilo, 2-oxo-1,3-diaza-cicloheptilo, morfolinilo, morfolinilamino, piperazinilo, piridinilo, piridiniloxi, piridinilamino, piridinilmetilo, piridinilmetoxi, pirimidinilo, pirimidiniloxi, pirimidinilmetilo o pirimidinilmetoxi. or represents heterocyclyl, heterocyclyloxy, heterocyclylamino, the grouping -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclyl alkylamino monocyclic / a or bicyclic / a, in each case eventually substituted with nitro, cyano, fluoro, methyl, bromo e methyl - or i-propyl, n-, i-, s- or t-butyl, 10 difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylthio, methylthio , n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, taken from the furyl series, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, tetrahydrofurylmethyl, 15 , tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylmethyl, dithiolanyl, dithiolanylmethyl, d itiolanilmetoxi, ditiolanilmetilamino, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl 20, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinilo, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl , dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl), tetrahydro- (2H) -1,2-oxazin-2-yl, tetrahydroisoxazolyl (isoxazolidinyl), thiazolyl (thiazolyl), thiazolyl (tetrazolothyl), thiazolyl, tetrahydrazyl (thiazolyl), thiazolyl (tetrazolothyl), thiazolyl (tetrazolothyl), thiazolyl (tetrazolothyl), thiazolyl (tetrazolothyl), thiazolyl (tetrahydrazol), thiazolyl (tetrazolothyl) thiazolidinyl), 25 tiazolimino, oxotiazolidinilo, cianoiminotiazolidinilo, oxadiazolilamino, tiadiazolilamino, oxotriazolinilo, oxatetrazolinilmetilo, tetrazolylmethyl, oxotetrazolinilo, oxotetrazolinilmetilo, tetrazolylmethyl, dioxanyl, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, dithianyl, ditianilmetilo, ditianilmetoxi, ditianilmetilamino, triazolilamino, piperidinyl, piperidinila Mino, 2- (1 H) -pyridinimino, 30-oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinyl amino , piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy.
R1 y R2 de manera sumamente preferida, representan hidrógeno. 35 R1 and R2 most preferably represent hydrogen. 35
R3 de manera sumamente preferida, representa hidrógeno, fluoro, cloro, metilo, etilo, trifluorometilo, triclorometilo, metoxi, etoxi, metilsulfonilo o etilsulfonilo. R3 most preferably represents hydrogen, fluoro, chloro, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl.
R4 de manera sumamente preferida representa hidrógeno, fluoro, cloro, metilo, trifluorometilo, triclorometilo, metoxi, etoxi, metilsulfonilo o etilsulfonilo. R4 most preferably represents hydrogen, fluoro, chloro, methyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl.
R5 de manera sumamente preferida representa hidrógeno 5 R5 most preferably represents hydrogen 5
Y de manera sumamente preferida representa hidroxi. And most preferably it represents hydroxy.
Son preferidos conforme al invento los compuestos de la fórmula (I), en los que se presenta una combinación de los significados precedentemente expuestos como preferidos. Compounds of the formula (I) are preferred according to the invention, in which there is a combination of the meanings set forth above as preferred.
Son especialmente preferidos conforme al invento los compuestos de la fórmula 10 (I), en los que se presenta una combinación de los significados precedentemente expuestos como especialmente preferidos. Especially preferred according to the invention are the compounds of the formula 10 (I), in which there is a combination of the meanings set forth above as especially preferred.
Son muy especialmente preferidos conforme al invento los compuestos de la fórmula (I), en los que se presenta una combinación de los significados precedentemente expuestos como muy especialmente preferidos. 15 Compounds of the formula (I), in which there is a combination of the meanings set forth above as very especially preferred, are very particularly preferred according to the invention. fifteen
Son sumamente preferidos conforme al invento los compuestos de la fórmula (I), en los que se presenta una combinación de los significados precedentemente expuestos como sumamente preferidos. Compounds of the formula (I) are highly preferred according to the invention, in which there is a combination of the meanings set forth above as highly preferred.
Un conjunto muy especialmente preferido es el de los compuestos de la fórmula general (I), en la que 20 A very especially preferred set is that of the compounds of the general formula (I), in which
Q representa O ó S, Q represents O or S,
R1 representa hidrógeno, representa metilo, etilo, n- o i-propilo, metiltio, etiltio, n- o i-propiltio, en cada caso eventualmente sustituido con fluoro o cloro, o representa fenilo, R1 represents hydrogen, represents methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, in each case eventually substituted with fluoro or chloro, or represents phenyl,
R2 representa hidrógeno, representa metilo, etilo, n- o i-propilo, en cada caso 25 eventualmente sustituido con fluoro o cloro, o eventualmente también en común con R1 representa etano-1,2-diílo, propano-1,3-diílo o butano-1,4-diílo. R2 represents hydrogen, represents methyl, ethyl, n- or i-propyl, in each case eventually substituted with fluoro or chloro, or possibly also in common with R1 represents ethane-1,2-diyl, propane-1,3-diyl or butane-1,4-diyl.
R3, R4 independientemente uno de otro, representan hidrógeno, nitro, ciano, fluoro, cloro, bromo, yodo, metilo, etilo, n- o i-propilo, difluorometilo, trifluorometilo, diclorometilo, triclorometilo, metoximetilo, metiltiometilo, metilsulfinilmetilo, 30 metilsulfonilmetilo, metoxi, etoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo, etilsulfonilo o dimetilaminosulfonilo. R3, R4 independently of each other, represent hydrogen, nitro, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, 30-methylsulfonylme , methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
R5 representa hidrógeno, representa metilo, etilo, n- o i-propilo, n- o i-butilo, en cada caso eventualmente sustituido con ciano, fluoro, cloro, metoxi o etoxi, representa metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, 35 R5 represents hydrogen, represents methyl, ethyl, n- or i-propyl, n- or i-butyl, in each case eventually substituted with cyano, fluoro, chloro, methoxy or ethoxy, represents methoxy, ethoxy, n- or i-propoxy , methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,
n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, metilamino, etilamino, n- o i-propilamino o dimetilamino, representa propenilo, butenilo, propinilo o butinilo, en cada caso eventualmente sustituido con fluoro y/o cloro, representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo o ciclohexilmetilo, en cada caso eventualmente sustituido con 5 ciano, fluoro, cloro o metilo, o representa fenilo, feniltio, fenilsulfinilo, fenilsulfonilo, fenilmetilo o feniletilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi o trifluorometoxi, o representa la agrupación -C(Q)-Z. 10 n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, represents propenyl, butenyl, propynyl or butynyl, in each case optionally substituted with fluoro and / or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case eventually substituted with cyano, fluoro, chloro or methyl, or represents phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl, in each case eventually substituted with nitro, cyano , fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, or represents the grouping -C (Q) -Z. 10
Y representa hidroxi, representa metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, metilsulfonilo, etilsulfonilo, acetiloxi, propioniloxi, n- o i-butiroíloxi, metoxicarboniloxi, etoxicarboniloxi, n- o i-propoxicarboniloxi, metilaminocarboniloxi, etilaminocarboniloxi, n- o i-propilaminocarboniloxi, metilsulfoniloxi, etilsulfoniloxi, n- o i-propilsulfoniloxi, en cada caso eventualmente 15 sustituido con fluoro y/o cloro, Y represents hydroxy, represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyloyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, ethoxycarbonyloxy, ethoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, in each case eventually substituted with fluoro and / or chlorine,
representa propeniloxi, buteniloxi, propiniloxi o butiniloxi, eventualmente sustituido en cada caso con fluoro, cloro y/o bromo, represents propenyloxy, butenyloxy, propynyloxy or butyloxy, optionally substituted in each case with fluoro, chloro and / or bromo,
representa feniloxi, feniltio, fenilsulfinilo, fenilsulfonilo, fenilcarboniloxi, fenilcarbonilmetoxi, fenilsulfoniloxi, fenilmetoxi, fenilmetiltio, fenilmetilsulfinilo o 20 fenilmetilsulfonilo, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metilsulfinilo, etilsulfinilo, trifluorometilsulfinilo, metilsulfonilo, etilsulfonilo o trifluorometilsulfonilo. 25 represents phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonymethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl, in each case optionally substituted with nitro, cyano, fluoro, methyl, chloro, methyl or methyl , n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulphinyl trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl. 25
Z representa amino, cianoamino, hidrazino, Z represents amino, cyanoamino, hydrazino,
representa metilo, sustituido con ciano, fluoro, cloro, metoxi, etoxi, n- o i-propoxi, metiltio, etiltio, n- o i-propiltio, metilsulfinilo, etilsulfinilo, n- o i- propilsulfinilo, metilsulfonilo o etilsulfonilo, represents methyl, substituted with cyano, fluoro, chloro, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethyl sulfonyl,
representa etenilo, propenilo, butenilo, etinilo, propinilo, butinilo, propeniloxi, 30 buteniloxi, propeniltio, buteniltio, propenilamino, butenilamino, propeniloxiamino, buteniloxiamino, etinilo, propinilo, butinilo, propiniloxi, butiniloxi, propinilamino o butinilamino, en cada caso eventualmente sustituido con fluoro y/o cloro, represents ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, propenyloxyamino, butenyloxyamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, optionally substituted or butylated in each case fluoro and / or chlorine,
representa ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilamino, ciclobutilamino, 35 represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, 35
ciclopentilamino, ciclohexilamino, ciclopentilhidrazino, ciclohexilhidrazino, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, ciclopentilmetoxi, ciclohexilmetoxi, ciclopropilmetilamino, ciclobutilmetilamino, ciclopentilmetilamino o ciclohexilmetilamino, en cada caso eventualmente sustituido con ciano, fluoro, 5 cloro o metilo, cyclopentylamino, cyclohexylamino, ciclopentilhidrazino, ciclohexilhidrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case optionally substituted by cyano, fluoro, 5-chloro or methyl,
representa fenilo, fenilcarbonilo, fenoxi, fenoxicarbonilo, feniltio, fenilamino, fenilhidrazino, fenilmetilo, feniletilo, fenilmetoxi, feniletoxi, fenilmetiltio, feniletiltio, fenilmetilamino o feniletilamino, en cada caso eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, 10 trifluorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, o represents phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino or phenylethylamino, in each case eventually substituted with nitro, cyano, fluoro, chloro, methyl, chloro, methyl , n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or
representa heterociclilo, heterocicliloxi, heterociclilamino, heterociclilalquilo, heterociclilalcoxi o heterociclilalquilamino monocíclico o bicíclico, eventualmente sustituido con nitro, ciano, fluoro, cloro, bromo, metilo, etilo, n- o i-propilo, n-, i-, s- 15 o t-butilo, difluorometilo, trifluorometilo, diclorometilo, triclorometilo, clorodifluorometilo, fluorodiclorometilo, metoxi, etoxi, n- o i-propoxi, difluorometoxi, trifluorometoxi, metiltio, etiltio, n- o i-propiltio, difluorometiltio, trifluorometiltio, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, tomado de la serie de furilo, tetrahidrofurilo, furiloxi, tetrahidrofuriloxi, furilamino, tetrahidrofurilamino, 20 furilmetilo, tetrahidrofurilmetilo, furilmetoxi, tetrahidrofurilmetoxi, furilmetilamino, tetrahidrofurilmetilamino, dioxolanilo, dioxolanilmetilo, dioxolanilmetoxi, dioxolanilmetilamino, tienilo, tienilmetilo, ditiolanilo, ditiolanilmetilo, ditiolanilmetoxi, ditiolanilmetilamino, pirrolidinilo, pirrolidinilamino, oxopirrolidinilo, pirrolilo, indolilo, pirrolilmetilo, pirazolilo, pirazoliloxi, pirazolilamino, pirazolilmetilo, imidazolilo, 25 imidazolinilo, imidazolilmetilo, imidazolinilmetilo, oxoimidazolinilo, 2-oxo-1,3-diaza-ciclopentilo, oxazolilo, oxazolilmetilo, oxotetrazolinilmetilo, tetrazolilmetilo, dihidrooxazolilo (oxazolinilo), tetrahidrooxazolilo (oxazolidinilo), isoxazolilo, dihidroisoxazolilo (isoxazolinilo), tetrahidroisoxalilo (isoxazolidinilo), tiazolilo, tiazolilmetilo, dihidrotiazolilo (tiazolinilo), tetrahidrotiazolilo (tiazolidinilo), 30 oxotiazolidinilo, cianoiminotiazolidinilo, oxotriazolinilo, oxotetrazolinilo, dioxanilo, dioxanilmetilo, dioxanilmetoxi, dioxanilmetilamino, ditianilo, ditianilmetilo, ditianilmetoxi, ditianilmetilamino, piperidinilo, piperidinilamino, oxopiperidinilo, 2-oxo-1,3-diaza-ciclohexilo, 2-oxo-1-aza-cicloheptilo, 2-oxo-1,3-diaza-cicloheptilo, morfolinilo, morfolinilamino, piperazinilo, piridinilo, piridiniloxi, piridinilamino, 35 represents heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkyl monocyclic or bicyclic, optionally substituted with nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, n-, i-, s- t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, taken from the series furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahidrofurilamino, 20 furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahidrofurilmetoxi, furylmethylamino, tetrahidrofurilmetilamino, dioxolanyl, dioxolanylmethyl, dioxolanilmetoxi, dioxolanilmetilamino, thienyl, thienylmethyl, dithiolanyl , dithiolanylmethyl, dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl, pyrrolidin ylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl 25, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinilo, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, oxotetrazolinilmetilo, tetrazolylmethyl, dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl), tetrahidroisoxalilo (isoxazolidinyl), thiazolyl, thiazolylmethyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), 30 oxotiazolidinilo, cianoiminotiazolidinilo, oxotriazolinilo, oxotetrazolinilo, dioxanyl, dioxanilmetilo, dioxanilmetoxi, dioxanylmethylamino, dithianyl, dithianylmethyl, dithianylmethoxy, dithianylmethylamino, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-1,3-diaza morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, 35
piridinilmetilo, piridinilmetoxi, pirimidinilo, pirimidiniloxi, pirimidinilmetilo o pirimidinilmetoxi. pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy.
Se resaltan especialmente los compuestos de las fórmulas (I-1) hasta (I-3): The compounds of the formulas (I-1) to (I-3) are especially highlighted:
5 5
Q, R1, R2, R3, R4, R5, Y y Z tienen en este caso cada vez los significados indicados más arriba como muy especialmente preferidos. Q, R1, R2, R3, R4, R5, Y and Z in this case each time have the meanings indicated above as very especially preferred.
Los radicales R3 o respectivamente R4 están situados a su vez preferentemente junto a la posición (2) o respectivamente (4) del anillo de fenilo. The radicals R3 or respectively R4 are in turn preferably located next to position (2) or respectively (4) of the phenyl ring.
Las definiciones de radicales generales arriba expuestas o expuestas en intervalos preferentes son válidas tanto para los productos finales de la fórmula (1) como también de manera correspondiente para los productos de partida o intermedios que se 5 necesitan en cada caso para la preparación. Estas definiciones de radicales se pueden combinar arbitrariamente unas con otras, por lo tanto también entre los intervalos preferidos que se indican. The definitions of general radicals set forth above or set out at preferred intervals are valid for both the final products of the formula (1) and also correspondingly for the starting or intermediate products that are needed in each case for the preparation. These radical definitions can be arbitrarily combined with each other, therefore also between the preferred ranges indicated.
En las definiciones precedentes y subsiguientes son válidas, siempre que no se señale otra cosa distinta, las siguientes definiciones: 10 In the preceding and subsequent definitions, the following definitions are valid, unless otherwise indicated: 10
Las cadenas de hidrocarbilo saturadas o insaturadas, tales como las de alquilo, alcanodiílo, alquenilo o alquinilo, también en unión con heteroátomos, tales como por ejemplo las de alcoxi, alquiltio o alquilamino, son en cada caso lineales o ramificadas. Se prefieren, en el caso de no se indique otra cosa distinta, cadenas de hidrocarbilo con 1 a 6 átomos de carbono. 15 The saturated or unsaturated hydrocarbyl chains, such as those of alkyl, alkanediyl, alkenyl or alkynyl, also in conjunction with heteroatoms, such as for example those of alkoxy, alkylthio or alkylamino, are in each case linear or branched. Hydrocarbyl chains with 1 to 6 carbon atoms are preferred, if not indicated otherwise. fifteen
Un arilo representa anillos de hidrocarbilo aromáticos, mono- o policíclicos, tales como p.ej. fenilo, naftilo, antranilo, fenantrilo, de manera preferida fenilo o naftilo, en particular fenilo. An aryl represents aromatic, mono- or polycyclic hydrocarbyl rings, such as eg phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Un heterociclilo representa compuestos de forma anular, saturados, insaturados o aromáticos, en los que por lo menos un miembro del anillo es un heteroátomo, es decir 20 un átomo diferente de carbono. Si el anillo contiene varios heteroátomos, éstos pueden ser iguales o diferentes. Los heteroátomos son de manera preferida oxígeno, nitrógeno o azufre. Si este anillo contiene varios átomos de oxígeno, éstos no están situados en posición contigua. Eventualmente, los compuestos de forma anular forman, en común con otros anillos carbocíclicos o heterocíclicos, condensados o puenteados, un sistema 25 de anillo policíclico, y los anillos condensados o puenteados forman en común un sistema de anillo policíclico. Un sistema de anillo policíclico puede estar unido a través del anillo heterocíclico o de un anillo carbocíclico condensado. Se prefieren los sistemas de anillos mono- o bicíclicos, en particular los sistemas de anillos monocíclicos con 5 a 6 miembros del anillo y los sistemas de anillos bicíclicos con 7 a 9 miembros de anillo. 30 A heterocyclyl represents ring-shaped, saturated, unsaturated or aromatic compounds, in which at least one member of the ring is a heteroatom, that is, a different carbon atom. If the ring contains several heteroatoms, they may be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If this ring contains several oxygen atoms, they are not located in an adjacent position. Eventually, the ring-shaped compounds form, in common with other carbocyclic or heterocyclic, condensed or bridged rings, a polycyclic ring system 25, and the condensed or bridged rings together form a polycyclic ring system. A polycyclic ring system may be linked through the heterocyclic ring or a condensed carbocyclic ring. Mono- or bicyclic ring systems are preferred, in particular monocyclic ring systems with 5 to 6 ring members and bicyclic ring systems with 7 to 9 ring members. 30
Un cicloalquilo representa compuestos de forma anular, carbocíclicos, saturados, que eventualmente forman con otros anillos carbocíclicos, condensados o puenteados, un sistema de anillo policíclico. Se prefieren, caso de que no se indique otra cosa distinta, ciclopropilo, ciclopentilo y ciclohexilo. A cycloalkyl represents ring-shaped, carbocyclic, saturated compounds that eventually form a polycyclic ring system with other carbocyclic rings, condensed or bridged. If not otherwise indicated, cyclopropyl, cyclopentyl and cyclohexyl are preferred.
Las nuevas benzoílciclohexenonas sustituidas de la fórmula general (I) se distinguen por una actividad herbicida fuerte y selectiva. The new substituted benzoylcyclohexenones of the general formula (I) are distinguished by a strong and selective herbicidal activity.
Se obtienen las nuevas benzoílciclohexenonas sustituidas de la fórmula general (I), cuando The new substituted benzoylcyclohexenones of the general formula (I) are obtained, when
se hacen reaccionar unas ciclohexanodionas (“hidroxiciclohexenonas”) de la fórmula 5 general (II) cyclohexanediones ("hydroxycyclohexenones") of the general formula (II) are reacted
en la que in which
R1 y R2 tienen los significados antes indicados, R1 and R2 have the meanings indicated above,
con unos ácidos benzoicos sustituidos de la fórmula general (III), 10 with substituted benzoic acids of the general formula (III), 10
en la que in which
Q, R3, R4, R5 y Z tienen los significados más arriba indicados, Q, R3, R4, R5 and Z have the meanings indicated above,
- o con unos derivados capaces de reaccionar de los mismos, tal como p.ej. con correspondientes halogenuros de ácidos, anhídridos de ácidos o ésteres - 15 - or with derivatives capable of reacting thereof, such as for example with corresponding acid halides, acid anhydrides or esters - 15
eventualmente en presencia de un agente de deshidratación, eventualmente en presencia de uno o varios agentes auxiliares de reacción y eventualmente en presencia de uno o varios agentes diluyentes, possibly in the presence of a dehydration agent, possibly in the presence of one or more auxiliary reaction agents and possibly in the presence of one or more diluting agents,
y eventualmente a continuación de ello, en los compuestos de la fórmula (I) obtenidos de esta manera se llevan a cabo, dentro del marco de la definición de los sustituyentes, de 20 un modo usual, reacciones de sustitución electrófilas o nucleófilas o respectivamente reacciones de oxidación o reducción, o los compuestos de la fórmula (I) se transforman de un modo usual en sales. and possibly following this, in the compounds of the formula (I) obtained in this way, electrophilic or nucleophilic substitution reactions or reactions respectively are carried out within the framework of the definition of the substituents. of oxidation or reduction, or the compounds of the formula (I) are transformed in the usual way into salts.
Las nuevas benzoílciclohexenonas sustituidas de la fórmula general (I) se pueden obtener en principio tal como se representa esquemáticamente a continuación: The new substituted benzoylcyclohexenones of the general formula (I) can be obtained in principle as schematically represented below:
Reacción de aminobenzoílciclohexenonas de la fórmula general (IV) con unos compuestos de halógeno(tio)carbonilo de la fórmula general (V) o eventualmente con unos correspondientes iso(tio)cianatos (Q, R1, R2, R3, R4, R5, Y y Z tienen los significados 5 arriba indicados, X representa halógeno): Reaction of aminobenzoylcyclohexenones of the general formula (IV) with halogen (thio) carbonyl compounds of the general formula (V) or possibly with corresponding iso (thio) cyanates (Q, R1, R2, R3, R4, R5, Y and Z have the meanings 5 indicated above, X represents halogen):
Los compuestos que se han de utilizar como sustancias de partida en los casos de los procedimientos () y () conformes al invento, están definidos generalmente por las fórmulas (IV) y (V). En las fórmulas (IV) y (V) Q, R1, R2, R3, R4, R5, Y y Z tienen 10 preferiblemente aquellos significados, que ya se indicaron más arriba, en conexión con la descripción de los compuestos de la fórmula (I) conformes al invento, como preferidos, especialmente preferidos, muy especialmente preferidos o como sumamente preferidos para Q, R1, R2, R3, R4, R5, Y y Z. The compounds to be used as starting substances in the cases of the processes () and () according to the invention are generally defined by formulas (IV) and (V). In formulas (IV) and (V) Q, R1, R2, R3, R4, R5, Y and Z preferably have those meanings, which are already indicated above, in connection with the description of the compounds of the formula ( I) according to the invention, as preferred, especially preferred, very especially preferred or as highly preferred for Q, R1, R2, R3, R4, R5, Y and Z.
Las sustancias de partida de la fórmula (V) son compuestos conocidos para un 15 experto en la especialidad. The starting substances of the formula (V) are compounds known to a person skilled in the art.
Las sustancias de partida de la fórmula (IV) se pueden obtener de una manera conocida para un experto en la especialidad. The starting substances of the formula (IV) can be obtained in a manner known to a person skilled in the art.
Reacción de iso(tio)cianatobenzoílciclohexenonas de la fórmula general (VI) con unos compuestos nucleófilos de la fórmula (VII); (Q, R1, R2, R3, R4, R5, Y y Z tienen en 20 este caso los significados arriba indicados): Reaction of iso (thio) cyanatobenzoylcyclohexenones of the general formula (VI) with nucleophilic compounds of the formula (VII); (Q, R1, R2, R3, R4, R5, Y and Z have in this case the meanings indicated above):
Si se utilizan por ejemplo la ciclohexano-1,3-diona y el ácido 2-cloro-4-[(dimetilaminocarbonil)-metilamino)]-benzoico como sustancias de partida, entonces el transcurso de la reacción en el caso del procedimiento conforme al invento se puede 5 esbozar mediante el siguiente esquema de fórmulas If, for example, cyclohexane-1,3-dione and 2-chloro-4 - [(dimethylaminocarbonyl) -methylamino)] -benzoic acid are used as starting substances, then the course of the reaction in the case of the process according to invention can be outlined by the following formula scheme
Las ciclohexanodionas que se han de utilizar en el caso del procedimiento conforme al invento como sustancias de partida para la preparación de compuestos de la fórmula general (I), se definen en términos generales por la fórmula (II). En la fórmula 10 general (II) R1 y R2 tienen de manera preferida aquellos significados, que ya se han indicado como preferidos, especialmente preferidos, muy especialmente preferidos o como sumamente preferidos para R1 y R2, más arriba en conexión con la descripción de los compuestos de la fórmula general (I) conformes al invento. The cyclohexanediones to be used in the case of the process according to the invention as starting substances for the preparation of compounds of the general formula (I), are defined in general terms by the formula (II). In the general formula (II) R1 and R2 preferably have those meanings, which have already been indicated as preferred, especially preferred, very especially preferred or as highly preferred for R1 and R2, above in connection with the description of the compounds of the general formula (I) according to the invention.
Las sustancias de partida de la fórmula general (II) son conocidas y/o se pueden 15 preparar de acuerdo con procedimientos en sí conocidos. The starting substances of the general formula (II) are known and / or can be prepared according to procedures known per se.
Los ácidos benzoicos sustituidos, que se han de utilizar adicionalmente como sustancias de partida en el caso del procedimiento conforme al invento, son definidos generalmente por la fórmula (III). En la fórmula (III) Q, R3, R4, R5 y Z tienen preferiblemente aquellos significados, que ya se indicaron más arriba como preferidos, 20 especialmente preferidos, muy especialmente o como sumamente preferidos para Q, R3, R4, R5 y Z en conexión con la descripción de los compuestos de la fórmula (I) conformes al invento. The substituted benzoic acids, which are to be used additionally as starting substances in the case of the process according to the invention, are generally defined by the formula (III). In the formula (III) Q, R3, R4, R5 and Z preferably have those meanings, which are already indicated above as preferred, especially preferred, very especially or as highly preferred for Q, R3, R4, R5 and Z in connection with the description of the compounds of the formula (I) according to the invention.
Las sustancias de partida de la fórmula general (III) son conocidas y/o se pueden preparar de acuerdo con procedimientos en sí conocidos (compárese el documento de solicitud de patente japonesa JP-A-11292849, Ejemplos de preparación). The starting substances of the general formula (III) are known and / or can be prepared according to procedures known per se (compare Japanese patent application document JP-A-11292849, Preparation Examples).
Se obtienen los ácidos benzoicos sustituidos de la fórmula general (III) cuando se hacen reaccionar ésteres de ácidos benzoicos de la fórmula general (IIIa) 5 The substituted benzoic acids of the general formula (III) are obtained when esters of benzoic acids of the general formula (IIIa) are reacted.
en la que in which
Q, R3, R4, R5 y Z tienen los significados arriba indicados, y Q, R3, R4, R5 and Z have the meanings indicated above, and
R representa alquilo, en particular representa metilo o etilo, R represents alkyl, in particular it represents methyl or ethyl,
con agua, eventualmente en presencia de un agente auxiliar de la hidrólisis, tal como p.ej. 10 lejía de sosa (una solución de hidróxido de sodio), y eventualmente en presencia de un agente diluyente, tal como p.ej. tetrahidrofurano, a unas temperaturas comprendidas entre 0ºC y 100ºC (compárense los Ejemplos de preparación). with water, possibly in the presence of an auxiliary hydrolysis agent, such as 10 sodium hydroxide solution (a solution of sodium hydroxide), and possibly in the presence of a diluting agent, such as, for example, tetrahydrofuran, at temperatures between 0 ° C and 100 ° C (compare Preparation Examples).
Los ésteres de ácidos benzoicos de la fórmula general (IIIa) que se necesitan como productos precursores, son conocidos y/o se pueden preparar de acuerdo con 15 procedimientos en sí conocidos (compárense el documento JP-A-11292849, Ejemplos de preparación). The esters of benzoic acids of the general formula (IIIa) that are needed as precursor products are known and / or can be prepared according to 15 known processes per se (compare JP-A-11292849, Preparation Examples).
Se obtienen los ésteres de ácidos benzoicos de la fórmula (IIIa), cuando The benzoic acid esters of the formula (IIIa) are obtained, when
() se hacen reaccionar unos ésteres de ácidos aminobenzoicos de la fórmula general (IX) 20 () aminobenzoic acid esters of the general formula (IX) are reacted
en la que in which
Q, R3, R4, R5 y Z tienen los significados arriba indicados y Q, R3, R4, R5 and Z have the meanings indicated above and
R representa alquilo, en particular representa metilo o etilo, R represents alkyl, in particular it represents methyl or ethyl,
con unos compuestos de halógeno(tio)carbonilo de la fórmula general (VI) 25 with halogen (thio) carbonyl compounds of the general formula (VI)
en la que in which
Q y Z tienen los significados arriba indicados y Q and Z have the meanings indicated above and
X representa halógeno, en particular fluoro, cloro o bromo, X represents halogen, in particular fluoro, chloro or bromo,
- o eventualmente con unos correspondientes iso(tio)cianatos - 5 - or possibly with corresponding iso (uncle) cyanates - 5
eventualmente en presencia de un aceptor de ácidos, tal como p.ej. carbonato de potasio o trietilamina, y eventualmente en presencia de un agente diluyente tal como p.ej. metil-isobutil-cetona o acetonitrilo, a unas temperaturas comprendidas entre 0ºC y 100ºC (compárense los Ejemplos de preparación), possibly in the presence of an acid acceptor, such as, for example, potassium carbonate or triethylamine, and possibly in the presence of a diluting agent such as, for example, methyl isobutyl ketone or acetonitrile, at temperatures between 0 ° C and 100 ° C (compare Preparation Examples),
o cuando 10 or when 10
() se hacen reaccionar unos ésteres de ácidos iso(tio)cianatobenzoicos de la fórmula general (X) () esters of iso (thio) cyanatobenzoic acids of the general formula (X) are reacted
en la que in which
Q, R3 y R4 tienen los significados arriba indicados, y 15 Q, R3 and R4 have the meanings indicated above, and 15
R representa alquilo, en particular representa metilo o etilo, R represents alkyl, in particular it represents methyl or ethyl,
con unos compuestos nucleófilos de la fórmula general (VIII) with nucleophilic compounds of the general formula (VIII)
en la que in which
Z tiene el significado más arriba indicado, 20 Z has the meaning indicated above, 20
eventualmente en presencia de un agente auxiliar de la reacción, tal como p.ej. trietilamina, y eventualmente en presencia de un agente diluyente, tal como p.ej. acetonitrilo o tolueno, a unas temperaturas comprendidas entre 10ºC y 120ºC (compárense los Ejemplos de preparación). possibly in the presence of a reaction auxiliary agent, such as eg triethylamine, and possibly in the presence of a diluting agent, such as, for example, acetonitrile or toluene, at temperatures between 10 ° C and 120 ° C (compare Examples of preparation).
Los compuestos que se han de utilizar como sustancias de partida en los casos 25 de los procedimientos (α) y (β) conformes al invento, están definidos en términos generales por las fórmulas (IX), (VI), (X) y (VIII). En las fórmulas (IX), (VI), (X) y (VIII) Q, The compounds to be used as starting substances in cases 25 of the processes (α) and (β) according to the invention are defined in general terms by formulas (IX), (VI), (X) and ( VIII). In formulas (IX), (VI), (X) and (VIII) Q,
R3, R4, R5 y Z tienen de manera preferida aquellos significados, que ya se indicaron más arriba como preferidos, especialmente preferidos, muy especialmente preferidos o como sumamente preferidos para Q, R3, R4, R5 y Z en conexión con la descripción de los compuestos de la fórmula (I) conformes al invento. R3, R4, R5 and Z preferably have those meanings, which are already indicated above as preferred, especially preferred, very especially preferred or as highly preferred for Q, R3, R4, R5 and Z in connection with the description of the compounds of the formula (I) according to the invention.
Las sustancias de partida de las fórmulas (VI) y (VIII) son unos compuestos 5 conocidos para un experto en la especialidad. The starting substances of the formulas (VI) and (VIII) are compounds known to a person skilled in the art.
Las sustancias de partida de las fórmulas (IX) y (X) se pueden obtener de un modo conocido para un experto en la especialidad. The starting substances of the formulas (IX) and (X) can be obtained in a manner known to a person skilled in the art.
El procedimiento conforme al invento para la preparación de las nuevas benzoílciclohexenonas sustituidas de la fórmula general (I) se lleva a cabo de manera 10 preferida mediando utilización de un agente de deshidratación. En este caso entran en cuestión los agentes químicos usuales que son apropiados para la fijación de agua. The process according to the invention for the preparation of the new substituted benzoylcyclohexenones of the general formula (I) is preferably carried out by using a dehydration agent. In this case, the usual chemical agents that are suitable for water fixing come into question.
Como ejemplos de ellos se han de mencionar diciclohexilcarbodiimida, anhídrido de ácido propanofosfónico y carbonil-bis-imidazol. Examples of them are dicyclohexylcarbodiimide, propanophosphonic acid anhydride and carbonyl bis-imidazole.
Como agentes de deshidratación especialmente bien apropiados se han de 15 mencionar diciclohexilcarbodiimida y anhídrido de ácido propanofosfónico. As especially suitable dehydration agents, dicyclohexylcarbodiimide and propanophosphonic acid anhydride should be mentioned.
El procedimiento conforme al invento para la preparación de las nuevas benzoílciclohexenonas de la fórmula general (I) se lleva a cabo eventualmente mediando utilización de un agente auxiliar de la reacción. The process according to the invention for the preparation of the new benzoylcyclohexenones of the general formula (I) is optionally carried out through the use of an auxiliary reaction agent.
Como ejemplos de éste se han de mencionar cianuro de sodio, cianuro de 20 potasio, cianhidrina de acetona, 2-ciano-2-(trimetilsililoxi)-propano y cianuro de trimetilsililo. As examples thereof, sodium cyanide, potassium cyanide, acetone cyanohydrin, 2-cyano-2- (trimethylsilyloxy) -propane and trimethylsilyl cyanide are mentioned.
Como agente auxiliar de la reacción especialmente bien apropiado se ha de mencionar el cianuro de trimetilsililo. As an especially suitable reaction auxiliary agent, trimethylsilyl cyanide should be mentioned.
El procedimiento conforme al invento se lleva a cabo de manera preferida 25 mediando utilización de uno o varios agentes auxiliares de la reacción. Como agentes auxiliares de la reacción para el procedimiento conforme al invento entran en cuestión en general las bases o los aceptores de ácidos inorgánicas/os u orgánicas/os que son usuales. A ellos pertenecen de manera preferida acetatos, amiduros, carbonatos, hidrógenocarbonatos, hidruros, hidróxidos o alcanolatos de metales alcalinos o alcalino-30 térreos, tales como acetato de sodio, potasio o calcio, amiduro de litio, sodio, potasio o calcio, carbonato de sodio, potasio o calcio, hidrógenocarbonato de sodio, potasio o calcio, hidruro de litio, sodio, potasio o calcio, hidróxido de litio, sodio, potasio o calcio, metanolato, etanolato, n- o i-propanolato, n-, i-, s- o -t-butanolato de sodio o potasio; además también unos compuestos orgánicos de carácter básico, tales como por ejemplo 35 The process according to the invention is preferably carried out by using one or more auxiliary agents of the reaction. As auxiliary agents of the reaction for the process according to the invention, the bases or acceptors of inorganic / organic or organic acids which are usual are generally in question. To them belong preferably acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkali metal or alkaline earth alkanolates, such as sodium acetate, potassium or calcium, lithium amide, sodium, potassium or calcium, carbonate sodium, potassium or calcium, sodium hydrogen carbonate, potassium or calcium, lithium hydride, sodium, potassium or calcium, lithium hydroxide, sodium, potassium or calcium, methanolate, ethanolate, n- or i-propanolate, n-, i- , s- or -t-sodium or potassium butanolate; also also basic organic compounds, such as for example 35
trimetilamina, trietilamina, tripropilamina, tributilamina, etil-diisopropilamina, N,N-dimetil-ciclohexilamina, diciclohexilamina, etil-diciclohexilamina, N,N-dimetil-anilina, N,N-dimetil-bencilamina, piridina, 2-metil-, 3-metil-, 4-metil-, 2,4-dimetil-, 2,6-dimetil-, 3,4-dimetil- y 3,5-dimetil-piridina, 5-etil-2-metil-piridina, 4-dimetilamino-piridina, N-metil-piperidina, N-etil-piperidina, N-metil-morfolina, N-etil-morfolina, 1,4-diazabiciclo[2.2.2]-octano (DABCO), 5 1,5-diazabiciclo[4.3.0]-non-5-eno (DBN), o 1,8-diazabiciclo[5.4.0]-undec-7-eno (DBU). trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl -methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4- dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine, N-methyl-morpholine, N-ethyl-morpholine, 1,4-diazabicyclo [2.2.2] -octane (DABCO), 5 1,5-diazabicyclo [4.3.0] -non-5-eno (DBN), or 1,8-diazabicyclo [5.4.0] -undec-7-eno (DBU).
Como otros agentes auxiliares de la reacción para el procedimiento conforme al invento entran en consideración también catalizadores de transferencia de fases. Como ejemplos de tales catalizadores se han de mencionar: As other reaction auxiliary agents for the process according to the invention, phase transfer catalysts are also considered. As examples of such catalysts are mentioned:
Bromuro de tetrabutil-amonio, cloruro de tetrabutil-amonio, cloruro de tetraoctil-amonio, 10 hidrógenosulfato de tetrabutil-amonio, cloruro de metil-trioctil-amonio, cloruro de hexadecil-trimetil-amonio, bromuro de hexadecil-trimetil-amonio, cloruro de bencil-trimetil-amonio, cloruro de bencil-trietil-amonio, hidróxido de bencil-trimetil-amonio, hidróxido de bencil-trietil-amonio, cloruro de bencil-tributil-amonio, bromuro de bencil-tributil-amonio, bromuro de tetrabutil-fosfonio, cloruro de tetrabutil-fosfonio, bromuro de tributil-hexadecil-15 fosfonio, cloruro de butil-trifenil-fosfonio, bromuro de etil-trioctil-fosfonio y bromuro de tetrafenil-fosfonio. Tetrabutyl ammonium bromide, tetrabutyl ammonium chloride, tetraoctyl ammonium chloride, 10 tetrabutyl ammonium hydrogensulfate, methyl trioctyl ammonium chloride, hexadecyl trimethyl ammonium chloride, hexadecyl trimethyl ammonium bromide, chloride of benzyl trimethyl ammonium, benzyl triethyl ammonium chloride, benzyl trimethyl ammonium hydroxide, benzyl triethyl ammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributyl ammonium bromide, tetrabutyl bromide -phosphonium, tetrabutyl phosphonium chloride, tributyl-hexadecyl-15-phosphonium bromide, butyl-triphenyl-phosphonium chloride, ethyl-trioctyl-phosphonium bromide and tetraphenyl-phosphonium bromide.
El procedimiento conforme al invento para la preparación de los compuestos de la fórmula general (I) se lleva a cabo preferiblemente en cada caso mediando utilización de uno o varios agentes diluyentes. Como agentes diluyentes para la realización del 20 procedimiento conforme al invento entran en consideración sobre todo disolventes orgánicos inertes. A ellos pertenecen en particular hidrocarburos alifáticos, alicíclicos o aromáticos, eventualmente halogenados, tales como por ejemplo bencina, benceno, tolueno, xileno, clorobenceno, diclorobenceno, éter de petróleo, hexano, ciclohexano, diclorometano, cloroformo, tetracloruro de carbono; éteres, tales como dietil-éter, 25 diisopropil-éter, dioxano, tetrahidrofurano o el éter dimetílico o dietílico de etilenglicol; cetonas, tales como acetona, butanona o metil-isobutil-cetona; nitrilos, tales como acetonitrilo, propionitrilo o butironitrilo; amidas, tales como N,N-dimetil-formamida, N,N-dimetil-acetamida, N-metil-formanilida, N-metil-pirrolidona o hexametil-triamida de ácido fosfórico; ésteres tales como el éster metílico de ácido acético o el éster etílico de ácido 30 acético; sulfóxidos, tales como dimetil-sulfóxido; alcoholes. tales como metanol, etanol, n- o i-propanol, éter monometílico de etilenglicol, éter monoetílico de etilenglicol, éter monometílico de di(etilenglicol) o éter monoetílico de di(etilenglicol). The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out in each case by using one or more diluting agents. As diluting agents for carrying out the process according to the invention, especially inert organic solvents are considered. To them belong in particular aliphatic, alicyclic or aromatic hydrocarbons, possibly halogenated, such as for example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethyl-formamide, N, N-dimethyl-acetamide, N-methyl-formailide, N-methyl-pyrrolidone or hexamethyl-triamide of phosphoric acid; esters such as acetic acid methyl ester or acetic acid ethyl ester; sulfoxides, such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n- or i-propanol, monomethyl ether of ethylene glycol, monoethyl ether of ethylene glycol, monomethyl ether of di (ethylene glycol) or monoethyl ether of di (ethylene glycol).
Las temperaturas de la reacción se pueden hacer variar en un mayor intervalo en el caso de la realización del procedimiento conforme al invento. Por lo general, se trabaja 35 The reaction temperatures can be varied over a longer range in the case of performing the process according to the invention. Usually it works 35
a unas temperaturas comprendidas entre 0ºC y 150ºC, de manera preferida entre 10ºC y 120ºC. at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
El procedimiento conforme al invento se lleva a cabo por lo general bajo una presión normal. Sin embargo, también es posible realizar el procedimiento conforme al invento bajo una presión elevada o reducida - en general comprendida entre 0,1 bares y 5 10 bares -. The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under a high or reduced pressure - in general between 0.1 bar and 5-10 bar -.
Para la realización del procedimiento conforme al invento, las sustancias de partida se emplean en general en unas cantidades aproximadamente equimolares. Sin embargo, también es posible utilizar uno de los componentes en un exceso mayor. La reacción se lleva a cabo en general en el seno de un apropiado agente diluyente en 10 presencia de un agente auxiliar de la reacción y la mezcla de reacción se agita en general durante varias horas a la temperatura necesaria. El tratamiento es llevado a cabo de acuerdo con métodos usuales (compárese los Ejemplos de preparación). For carrying out the process according to the invention, the starting substances are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out within an appropriate diluting agent in the presence of an auxiliary reaction agent and the reaction mixture is generally stirred for several hours at the necessary temperature. The treatment is carried out according to usual methods (compare Preparation Examples).
Las sustancias activas conformes al invento se pueden utilizar como agentes desfoliantes, desecantes, agentes para la destrucción de hierbas y en particular como 15 agentes para la aniquilación de malezas. Como una maleza han de entenderse en su sentido más amplio todas las plantas, que crecen en sitios, en donde ellas son indeseadas. El hecho de si las sustancias conformes al invento actúen como herbicidas totales o selectivos, depende en lo esencial de la cantidad consumida. Las sustancias activas conformes al invento se pueden utilizar p.ej. en los casos de las siguientes 20 plantas: The active substances according to the invention can be used as scrubbing agents, desiccants, agents for the destruction of herbs and in particular as agents for the annihilation of weeds. As a weed they have to be understood in their broadest sense all plants, which grow in places, where they are unwanted. Whether the substances according to the invention act as total or selective herbicides, depends essentially on the amount consumed. The active substances according to the invention can be used eg in the cases of the following 20 plants:
Malezas dicotiledóneas de los géneros: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, 25 Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Euphorbia, Euphorbia, Euphorbia, Gap Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, 25 Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Senegal , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Plantas cultivadas dicotiledóneas de los géneros: Arachis, Beta, Brassica, 30 Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. Dicotyledonous cultivated plants of the genera: Arachis, Beta, Brassica, 30 Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Malezas monocotiledóneas de los géneros: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, 35 Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, 35
Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Plantas cultivadas monocotiledóneas de los géneros: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 5 Cultivated monocot plants of the genera: Allium, Ananas, Asparagus, Oats, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 5
La utilización de las sustancias activas conformes al invento no está limitada, sin embargo, de ninguna de las maneras a estos géneros, sino que se extiende de igual manera también a otras plantas. The use of the active substances according to the invention is not limited, however, in any way to these genera, but also extends to other plants as well.
Las sustancias activas conformes al invento son apropiadas, dependiendo de la concentración, para la represión total de malezas, p.ej. en instalaciones industriales y de 10 vías ferroviarias, y en caminos y plazas con o sin vegetación de arbolado. Asimismo, las sustancias activas conformes al invento se pueden emplear para la represión de malezas en cultivos permanentes, p.ej. bosques, plantaciones de árboles de madera ornamental, frutícolas, vinícolas, citrícolas, nogales, bananales, café, té, caucho, palma oleífera, cacao, frutas de bayas y lúpulo, en céspedes ornamentales y deportivos, y en superficies 15 de prados, así como para la represión selectiva de malezas en cultivos monoanuales. The active substances according to the invention are appropriate, depending on the concentration, for the total repression of weeds, eg in industrial facilities and 10 railway tracks, and on roads and squares with or without woodland vegetation. Likewise, the active substances according to the invention can be used for the suppression of weeds in permanent crops, eg forests, tree plantations of ornamental, fruit, wine, citrus, walnut, bananas, coffee, tea, rubber, palm trees oleiferous, cocoa, berry fruits and hops, in ornamental and sports lawns, and on meadows 15 surfaces, as well as for the selective repression of weeds in single-year crops.
Los compuestos de la fórmula (I) conformes al invento muestran una fuerte actividad herbicida y un amplio espectro de efectos en el caso de la aplicación sobre el suelo y sobre las partes de las plantas situadas por encima de la tierra. Ellos son apropiados en cierto grado también para la represión selectiva de malezas 20 monocotiledóneas y dicotiledóneas en cultivos de plantas monocotiledóneas y dicotiledóneas, en el procedimiento tanto de antes del brote como también de después del brote. The compounds of the formula (I) according to the invention show a strong herbicidal activity and a wide spectrum of effects in the case of application on the soil and on the parts of the plants located above the earth. They are also suitable to a certain degree for the selective repression of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous plant cultures, in the procedure both before the outbreak and also after the outbreak.
Las sustancias activas conformes al invento se pueden utilizar, en determinadas concentraciones y respectivamente cantidades consumidas, también para la represión de 25 plagas animales y enfermedades fúngicas o bacterianas de las plantas. Eventualmente, ellas se pueden utilizar también como productos intermedios o precursores para la síntesis de otras sustancias activas. The active substances according to the invention can be used, in certain concentrations and respectively quantities consumed, also for the suppression of 25 animal pests and fungal or bacterial diseases of the plants. Eventually, they can also be used as intermediates or precursors for the synthesis of other active substances.
Conforme al invento, se pueden tratar todas las plantas y partes de plantas. Como plantas se entienden en este caso todas las plantas y poblaciones de plantas, tales como 30 plantas silvestres deseadas e indeseadas o plantas cultivadas (incluyendo plantas cultivadas que se presentan en la naturaleza). Las plantas cultivadas pueden ser unas plantas, que se pueden obtener por métodos convencionales de cultivación, procreación y optimización o por métodos de biotecnología y tecnología genética, o por combinaciones de estos métodos, incluyendo a las plantas transgénicas e incluyendo a 35 According to the invention, all plants and parts of plants can be treated. As plants, in this case, all plants and plant populations are understood, such as 30 desired and unwanted wild plants or cultivated plants (including cultivated plants that occur in nature). Cultivated plants can be plants, which can be obtained by conventional methods of cultivation, procreation and optimization or by methods of biotechnology and genetic technology, or by combinations of these methods, including transgenic plants and including 35
las variedades de plantas que son protegibles o no protegibles por derechos de protección de variedades. Como partes de plantas deben de entenderse todas las partes situadas por encima de la tierra y por debajo de la tierra, y todos los órganos de las plantas, tales como retoños, hojas, flores y raíces, señalándose a modo de ejemplo hojas, agujas, peciolos, tallos, troncos, flores, cuerpos de frutas, frutas y semillas, así como 5 raíces, tubérculos y rizomas. A las partes de plantas pertenecen también un material cosechado, así como un material de reproducción vegetativa y generativa, por ejemplo plantones, tubérculos, rizomas, esquejes y semillas. varieties of plants that are protectable or non-protectable by variety protection rights. As parts of plants should be understood all the parts located above the earth and below the earth, and all the organs of the plants, such as sprouts, leaves, flowers and roots, indicating by way of example leaves, needles, petioles, stems, trunks, flowers, fruit bodies, fruits and seeds, as well as 5 roots, tubers and rhizomes. To the parts of plants belong also a harvested material, as well as a vegetative and generative reproduction material, for example seedlings, tubers, rhizomes, cuttings and seeds.
El tratamiento conforme al invento de las plantas y las partes de plantas con las sustancias activas se efectúa de manera directa o por acción sobre su entorno, espacio 10 de vida o espacio de almacenamiento, de acuerdo con los métodos usuales de tratamiento, p.ej. por inmersión, atomización, proyección, evaporación, nebulización, esparcimiento, extensión y, en el caso de un material de reproducción, en particular en el caso de semillas, además por envolvimiento con una o múltiples capas. The treatment according to the invention of the plants and the parts of plants with the active substances is carried out directly or by action on their environment, living space 10 or storage space, according to the usual methods of treatment, e.g. By immersion, atomization, projection, evaporation, nebulization, spreading, extension and, in the case of a breeding material, in particular in the case of seeds, also by wrapping with one or multiple layers.
Las sustancias activas se pueden transformar en las formulaciones usuales, tales 15 como soluciones, emulsiones, polvos para proyectar, suspensiones, polvos, agentes para espolvorear, pastas, polvos solubles, granulados, concentrados para suspensión y emulsión, sustancias naturales y sintéticas impregnadas con sustancias activas, así como encapsulaciones finísimas en sustancias poliméricas. The active substances can be transformed into the usual formulations, such as solutions, emulsions, projecting powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, concentrates for suspension and emulsion, natural and synthetic substances impregnated with substances active, as well as very fine encapsulations in polymeric substances.
Estas formulaciones se preparan de una manera conocida, p.ej. por mezcladura 20 de las sustancias activas con agentes extendedores, es decir disolventes líquidos y/o materiales de soporte sólidos, eventualmente mediando utilización de agentes con actividad superficial (tensioactivos), por lo tanto agentes emulsionantes y/o agentes dispersantes y/o agentes generadores de espuma. These formulations are prepared in a known manner, eg by mixing 20 of the active substances with spreading agents, i.e. liquid solvents and / or solid support materials, possibly mediating the use of agents with surface activity (surfactants), whereby both emulsifying agents and / or dispersing agents and / or foam generating agents.
En el caso del uso de agua como agente extendedor, se pueden utilizar como 25 disolventes auxiliares p.ej. también disolventes orgánicos. Como disolventes líquidos entran en cuestión en lo esencial: compuestos aromáticos, tales como xileno, tolueno o alquilnaftalenos, compuestos aromáticos clorados e hidrocarburos alifáticos clorados, tales como clorobencenos, cloroetilenos o cloruro de metileno, hidrocarburos alifáticos, tales como ciclohexano o parafinas, p.ej. fracciones de petróleo, aceites minerales y 30 vegetales, alcoholes, tales como butanol o glicol, así como sus éteres y ésteres, cetonas tales como acetona, metil-etil-cetona, metil-isobutil-cetona o ciclohexanona, disolventes fuertemente polares, tales como dimetil-formamida y dimetil-sulfóxido, así como agua. In the case of the use of water as a spreading agent, they can be used as auxiliary solvents, eg also organic solvents. As liquid solvents, the following are essential: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. eg petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl formamide and dimethyl sulfoxide, as well as water.
Como materiales de soporte sólidos entran en cuestión: p.ej. sales de amonio y polvos finos de piedras naturales, tales como caolines, tierras arcillosas, talco, greda, 35 As solid support materials come into question: eg ammonium salts and fine powders of natural stones, such as kaolins, clay soils, talcum powder, clay, 35
cuarzo, attapulgita, montmorillonita o tierra de diatomeas y polvos finos de piedras sintéticas, tales como un ácido silícico muy disperso, un óxido de aluminio y silicatos, como materiales de soporte sólidos para granulados entran en cuestión: p.ej. piedras naturales machacadas y fraccionadas, tales como calcita, mármol, piedra pómez, sepiolita, dolomita, así como granulados sintéticos a base de polvos finos inorgánicos y 5 orgánicos, así como granulados a base de un material orgánico tales como aserrín, cáscaras de nuez de coco, mazorcas de maíz y tallos de tabaco; como agentes emulsionantes y/o generadores de espuma entran en cuestión: p.ej. agentes emulsionantes no ionógenos y aniónicos, tales como poli(oxietilen)-ésteres de ácidos grasos, poli(oxietilen)-éteres de alcoholes grasos, p.ej. alquilaril-poliglicol-éteres, 10 alquilsulfonatos, alquilsulfatos, arilsulfonatos así como materiales hidrolizados de proteínas; como agentes dispersantes entran en cuestión: p.ej. lejías residuales del procedimiento al sulfito para la obtención de lignina, y una metil-celulosa. Quartz, attapulgite, montmorillonite or diatomaceous earth and fine powders of synthetic stones, such as a widely dispersed silicic acid, an aluminum oxide and silicates, as solid support materials for granules come into question: eg crushed natural stones and fractionated, such as calcite, marble, pumice stone, sepiolite, dolomite, as well as synthetic granules based on inorganic and organic fine powders, as well as granules based on an organic material such as sawdust, coconut nut shells, cobs of corn and tobacco stalks; As emulsifying agents and / or foaming agents, the following are in question: eg non-ionic and anionic emulsifying agents, such as poly (oxyethylene) fatty acid esters, poly (oxyethylene) fatty alcohol ethers, eg. alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates as well as hydrolyzed protein materials; As dispersing agents, the following are: eg residual lye from the sulphite process to obtain lignin, and a methyl cellulose.
En las formulaciones se pueden utilizar agentes adhesivos, tales como carboximetil-celulosa, polímeros naturales y sintéticos, en forma pulverulenta, granular o 15 de látex, tales como goma arábiga, un poli(alcohol vinílico), un poli(acetato de vinilo), así como fosfolípidos naturales, tales como cefalinas y lecitinas, y fosfolípidos sintéticos. Otros aditivos pueden ser aceites minerales y vegetales. Adhesive agents, such as carboxymethyl cellulose, natural and synthetic polymers, in powdered, granular or latex form, such as gum arabic, a polyvinyl alcohol, a polyvinyl acetate, can be used in the formulations. as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Se pueden utilizar colorantes, tales como pigmentos inorgánicos, p.ej. un óxido de hierro, óxido de titanio, azul de ferrocianuro y colorantes orgánicos, tales como colorantes 20 de alizarina, azoicos y de metal-ftalocianina, y sustancias nutritivas trazas tales como sales de hierro, manganeso, boro, cobre, cobalto, molibdeno y zinc. Dyes, such as inorganic pigments, eg an iron oxide, titanium oxide, ferrocyanide blue and organic dyes, such as alizarin, azoic and metal-phthalocyanine dyes, and trace nutrients such as trace substances such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Las formulaciones contienen por lo general entre 0,1 y 95 por ciento en peso de una sustancia activa, de modo preferido entre 0,5 y 90 %. The formulations generally contain between 0.1 and 95 percent by weight of an active substance, preferably between 0.5 and 90%.
Las sustancias activas conformes al invento se pueden utilizar como tales o en 25 sus formulaciones también en mezcla con herbicidas conocidos y/o con unas sustancias que mejoran la compatibilidad con las plantas cultivadas ("antídotos") para la represión de malezas, siendo posibles unas formulaciones acabadas o unas mezclas de depósito. Por lo tanto, son posibles también unas mezclas con agentes para la represión de malezas, que contienen uno o varios herbicidas conocidos y un antídoto. 30 The active substances according to the invention can be used as such or in their formulations also in admixture with known herbicides and / or with substances that improve compatibility with cultivated plants ("antidotes") for weed suppression, being possible finished formulations or tank mixes. Therefore, mixtures with weed repression agents, which contain one or more known herbicides and an antidote, are also possible. 30
Para las mezclas entran en cuestión herbicidas conocidos, por ejemplo Known herbicides come into question, for example
acetocloro, acifluorfeno (-sodio), aclonifeno, alacloro, aloxidim (-sodio), ametrina, amicarbazona, amidocloro, amidosulfurón, anilofos, asulam, atrazina, azafenidina, azimsulfurón, beflubutamida, benazolina (-etilo), benfuresato, bensulfurón (-metilo), bentazona, benzofendizona, benzobiciclón, benzofenap, benzoílprop (-etilo), bialafos, 35 acetochlor, acifluorfen (-sodium), aclonifen, alachlor, aloxidim (-sodium), ametrine, amicarbazone, amidochloro, amidosulfuron, anilophos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benamethylsulphon (benazoline, benzymethyl) ), bentazone, benzofendizona, benzobicyclone, benzophenap, benzoylprop (-ethyl), bialafos, 35
bifenox, bispiribac (-sodio), bromobutida, bromofenoxima, bromoxinilo, butacloro, butafenacilo (-alilo), butroxidim, butilato, cafenstrol, caloxidim, carbetamida, carfentrazona (-etilo), clometoxifeno, clorambén, cloridazona, clorimurón (-etilo), cloronitrofeno, clorosulfurón, clorotolurón, cinidón (-etilo), cinmetilina, cinosulfurón, clefoxidim, cletodim, clodinafop (-propargilo), clomazona, clomeprop, clopiralida, clopirasulfurón (-metilo), 5 cloransulam (-metilo), cumilurón, cianazina, cibutrina, cicloato, ciclosulfamurón, cicloxidim, cihalofop (-butilo), 2,4-D, 2,4-DB, desmedifam, dialato, dicamba, dicloroprop (-P), diclofop (-metilo), diclosulam, dietatilo (-etilo), difenzoquat, diflufenicán, diflufenzopir, dimefurón, dimepiperato, dimetacloro, dimetametrina, dimetenamida, dimexiflam, dinitramina, difenamida, diquat, ditiopir, diurón, dimrón, epropodán, EPTC, esprocarb, 10 etalfluralina, etametsulfurón (-metilo), etofumesato, etoxifeno, etoxisulfurón, etobenz-anida, fenoxaprop (-P-etilo), fentrazamida, flamprop (-isopropilo, -isopropilo-L, -metilo), flazasulfurón, florasulam, fluazifop (-P-butilo), fluazolato, flucarbazona (-sodio), flufenacet, flumetsulam, flumiclorac (-pentilo), flumioxazina, flumipropina, flumetsulam, fluometurón, fluorocloridona, fluoroglicofeno (-etilo), flupoxam, flupropacilo, flurpirsulfurón (-metilo, -15 sodio), flurenol (-butilo), fluridona, fluroxipir (-butoxipropilo, -meptilo), flurprimidol, flur-tamona, flutiacet (-metilo), flutiamida, fomesafeno, foramsulfurón, glufosinato (-amonio), glifosato (-isopropilamonio), halosafeno, haloxifop (-etoxietilo, -P-metilo), hexazinona, imazametabenz (-metilo), imazametapir, imazamox, imazapic, imazapir, imazaquin, imazetapir, imazosulfurón, yodosulfurón (-metilo, -sodio), ioxinilo, isopropalina, 20 isoproturón, isourón, isoxabeno, isoxaclortol, isoxaflutol, isoxapirifop, lactofeno, lenacilo, linurón, MCPA, mecoprop, mefenacet, mesotriona, metamitrón, metazacloro, metabenzotiazurón, metobenzurón, metobromurón, (alfa-) metolacloro, metosulam, metoxurón, metribuzina, metsulfurón (-metilo), molinato, monolinurón, naproanilida, napropamida, neburón, nicosulfurón, norflurazona, orbencarb, orizalina, oxadiargilo, 25 oxadiazona, oxasulfurón, oxaziclomefona, oxifluorfeno, paraquat, ácido pelargónico, pendimetalina, pendralina, pentoxazona, fenmedifam, picolinafeno, piperofos, pretilacloro, primisulfurón (-metilo), profluazol, prometrina, propacloro, propanilo, propaquizafop, prop-isocloro, propoxicarbazona (-sodio), propizamida, prosulfocarb, prosulfurón, piraflufeno (-etilo), pirazogilo, pirazolato, pirazosulfurón (-etilo), pirazoxifeno, piribenzoxima, piributi-30 carb, piridato, piridatol, pirftalida, piriminobac (-metilo), piritiobac (-sodio), quinclorac, quin-merac, quinoclamina, quizalofop (-P-etilo, -P-tefurilo), rimsulfurón, setoxidim, simazina, simetrina, sulcotriona, sulfentrazona, sulfometurón (-metilo), sulfosato, sulfosulfurón, tebutam, tebutiurón, tepraloxidim, terbutilazina, terbutrina, tenilcloro, tiafluamida, tiazopir, tidiazimina, tifensulfurón (-metilo), tiobencarb, tiocarbazilo, tralkoxidim, trialato, triasulf-35 bifenox, bispiribac (-sodium), bromobutide, bromofenoxime, bromoxynil, butachlor, butafenacil ((allyl), butroxidim, butylate, cafenstrol, caloxidim, carbetamide, carfentrazone (-ethyl), chlomethoxyphene, chlorambethenyl, chlorambethenyl, chlorambethenyl, chlorambethenyl, chlorambetone, chlorambethenyl chloronitrofen, chlorosulfuron, chlorotoluron, cinidon (-ethyl), cinmethyline, cinosulfuron, clefoxidim, cletodim, clodinafop (-propargyl), clomazone, clomeprop, clopiralida, clopirasulfuron (-methyl), 5 chloransulam (-methyl), cumiluronine , cycloate, cyclosulfamuron, cycloxidim, cihalofop (-butyl), 2,4-D, 2,4-DB, desmedifam, dialate, dicamba, dichloroprop (-P), diclofop (-methyl), diclosulam, diethyl (-ethyl) , diphenzoquat, diflufenican, diflufenzopir, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimetenamide, dimexiflam, dinitramine, diphenamide, diquat, dithiopyr, diuron, dimron, epropodan, EPTC, esprocarb, 10-meth-ethamphephthalophene, phenoephthaphthalene, ethylophthalophenephthaphthalene ethoxy sulfur, ethobenz-anide , phenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumracula (-pentyl), flumioxazine, flumipropin, flumetsulam, fluometuron, fluorochloridone, fluoroglycophene (-ethyl), flupoxam, flupropacillus, flurpirsulfuron (-methyl, -15 sodium), flurenol (-butyl), fluridone, fluroxypyl (dipropyl-diphenyl) ), flurprimidol, flur-tamona, flutiacet (-methyl), flutiamide, fomesaphene, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosaphene, haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazametaben methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon 20, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA , mecoprop, mefenacet, mesotrione, methamitron, metazachlor, metabenzothiazuron, metobenzuron, metobromuron, (alpha-) metolachloro, metosulam, methoxuron, metribuzine, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazone, orbencarb, oxadiazonazine oxazonazonazine, oxazadiazonazine, oxazadiazonazine, oxazadiazonazine, oxazyl azazonazine, oxazadyl azamothinone , oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendraline, pentoxazone, fenmedifam, picolinaphene, piperofos, prethylachloro, primisulfuron (-methyl), profluazole, promethrine, propachloro, propanyl, propaquizafop, prop-isochlorodio, pro-xylorozodone, prosulfocarb, prosulfuron, pyrafluphene (-ethyl), pyrazogyl, pyrazolate, pyrazulfuron (-ethyl), pyrazoxyphene, pyribenzoxime, pyributi-30 carb, pyridate, pyridatol, pyrftalide, pyriminobac (-methyl), piritiobac (-sodium), quincea, quincea -merac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, setoxidim, simazine, simetrin, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfate, sulfosulfur ón, tebutam, tebutiuron, tepraloxidim, terbutylazine, terbutrine, tenylchloro, thiafluamide, thiazopir, thidiazimine, tifensulfuron (-methyl), thiobencarb, thiocarbazyl, tralkoxidim, trialate-triasulf
urón, tribenurón (-metilo), triclopir, tridifano, trifluralina, trifloxisulfurón, triflusulfurón (-metilo), tritosulfurón. uron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxisulfuron, triflusulfuron (-methyl), tritosulfuron.
Para las mezclas entran en cuestión además antídotos conocidos, por ejemplo In addition, known antidotes also come into question, for example
AD-67, BAS-145138, benoxacor, cloquintocet (-mexilo), ciometrinilo, 2,4-D, DKA-24, dicloromida, dimrón, fenclorim, fenclorazol (-etilo), flurazol, fluxofenim, furilazol, 5 isoxadifeno (-etilo), MCPA, mecoprop (-P), mefenpir (-dietilo), MG-191, oxabetrinilo, PPG-1292, R-29148. AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinyl, 2,4-D, DKA-24, dichloromide, dimron, fenclorim, pheclorazol (-ethyl), flurazole, fluxophenim, furilazole, 5 isoxadifen (- ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinyl, PPG-1292, R-29148.
También es posible una mezcla con otras sustancias activas conocidas, tales como fungicidas, insecticidas, acaricidas, nematicidas, sustancias protectoras contra el ataque de los pájaros, sustancias nutritivas de las plantas y agentes para mejorar la 10 estructura de los suelos. It is also possible to mix with other known active substances, such as fungicides, insecticides, acaricides, nematicides, protective substances against the attack of birds, nutrients of plants and agents to improve the structure of soils.
Las sustancias activas se pueden utilizar como tales, en forma de sus formulaciones o de las formas de utilización preparadas a partir de ellas por dilución adicional, tales como soluciones, suspensiones, emulsiones, polvos, pastas y granulados, que están prestas / prestos para el uso. La aplicación se efectúa de un modo usual, p.ej. 15 por vertimiento, proyección, rociadura o esparcimiento. The active substances can be used as such, in the form of their formulations or of the forms of use prepared therefrom by additional dilution, such as solutions, suspensions, emulsions, powders, pastes and granules, which are ready / ready for use. use. The application is carried out in a usual way, eg 15 by pouring, spraying, spraying or spreading.
Las sustancias activas conformes al invento se pueden aplicar tanto antes como también después del brote de las plantas. Se pueden incorporar en el suelo también antes de la siembra. The active substances according to the invention can be applied both before and after the plant sprout. They can be incorporated into the soil also before planting.
La cantidad aplicada de sustancia activa puede fluctuar en un gran intervalo. Ésta 20 depende en lo esencial del tipo del efecto deseado. Por lo general, las cantidades consumidas están situadas entre 1 g y 10 kg de sustancia activa por hectárea de superficie del suelo, preferiblemente entre 5 g y 5 kg por ha. The applied amount of active substance may fluctuate over a large range. This essentially depends on the type of the desired effect. Generally, the quantities consumed are between 1 g and 10 kg of active substance per hectare of soil surface, preferably between 5 g and 5 kg per ha.
Tal como ya se ha mencionado anteriormente, se pueden tratar conforme al invento todas las plantas y sus partes. En una forma preferida de realización, se tratan 25 especies de plantas y variedades de plantas que se presentan en estado silvestre u obtenidas por métodos convencionales de cultivación o procreación biológica, tales como cruce o fusión de protoplastos, así como sus partes. En una forma preferida adicional de realización, se tratan plantas transgénicas y variedades de plantas que se habían obtenido por métodos de tecnología genética, eventualmente en combinación con 30 métodos convencionales (organismos modificados genéticamente, en inglés genetically modified organisms) y sus partes. El concepto de "partes" o respectivamente "partes de plantas" o "partes de vegetales" se explicó más arriba. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, 25 species of plants and varieties of plants that are presented in the wild or obtained by conventional methods of cultivation or biological procreation, such as crossing or fusion of protoplasts, as well as their parts are treated. In a further preferred embodiment, transgenic plants and plant varieties that had been obtained by genetic technology methods, optionally in combination with 30 conventional methods (genetically modified organisms, genetically modified organisms) and their parts are treated. The concept of "parts" or respectively "parts of plants" or "parts of vegetables" was explained above.
De modo especialmente preferido se tratan plantas conformes al invento de las variedades de plantas que en cada caso son usuales en el comercio o que se encuentran 35 Especially preferred are treated plants according to the invention of the varieties of plants that in each case are usual in commerce or that are found in
en uso. Como variedades de plantas se entienden las plantas con determinadas propie-dades ("rasgos", en inglés "traits"), que se han obtenido por cultivación convencional, por mutagénesis, o también por técnicas de ADN recombinante. Éstas pueden ser variedades, biotipos y genotipos. In use. Plant varieties are understood as plants with certain properties ("traits" in English "traits"), which have been obtained by conventional cultivation, by mutagenesis, or also by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
Dependiendo de las especies de plantas o respectivamente de las variedades de 5 plantas, de su sitio de estancia y de las condiciones de crecimiento (suelos, climas, períodos de vegetación, nutrición) pueden aparecer mediante el tratamiento conforme al invento también efectos superiores a los aditivos ("sinérgicos"). Así, por ejemplo, son posibles unas cantidades consumidas disminuidas y/o unas ampliaciones del espectro de efectos y/o un refuerzo del efecto de las sustancias y de los agentes utilizables conformes 10 al invento - también en combinación con otras sustancias activas agroquímicas -, un mejor crecimiento de las plantas cultivadas, una tolerancia aumentada de las plantas cultivadas frente a temperaturas altas o bajas, una tolerancia aumentada de las plantas cultivadas frente a la sequedad o frente al contenido de agua o respectivamente de sales del suelo, un rendimiento aumentado de floración, una cosecha facilitada, una 15 aceleración de la maduración, mayores rendimientos de cosechas, una calidad más alta y/o un poder nutritivo más alto de los productos cosechados, una más alta capacidad de almacenamiento y/o elaborabilidad de los productos cosechados, que va más allá de los efectos que propiamente son de esperar. Depending on the species of plants or respectively of the varieties of 5 plants, their place of residence and the growth conditions (soils, climates, periods of vegetation, nutrition), effects superior to the effects of the invention can also occur additives ("synergistic"). Thus, for example, decreased quantities consumed and / or extensions of the spectrum of effects and / or a reinforcement of the effect of the substances and of the usable agents according to the invention are possible - also in combination with other agrochemical active substances -, a better growth of the cultivated plants, an increased tolerance of the cultivated plants against high or low temperatures, an increased tolerance of the cultivated plants against dryness or against the water content or respectively of soil salts, an increased yield of flowering, a facilitated harvest, an acceleration of ripening, higher yields of crops, a higher quality and / or a higher nutritional power of harvested products, a higher storage capacity and / or processability of harvested products, that goes beyond the effects that are expected.
A las preferidas plantas o respectivamente variedades de plantas transgénicas 20 (obtenidas por tecnología genética) que se han de tratar conforme al invento, pertenecen todas las plantas que se habían obtenido mediante la modificación por tecnología genética de un material genético, que confiere a estas plantas unas propiedades ("rasgos") valiosas especialmente ventajosas. Ejemplos de tales propiedades son un mejor crecimiento de las plantas, una tolerancia aumentada frente a temperaturas altas o 25 bajas, una tolerancia aumentada frente a la sequedad o frente al contenido de agua o respectivamente de sales del suelo, un rendimiento aumentado de floración, una cosecha facilitada, una aceleración de la maduración, rendimientos más altos de cosechas, una calidad más alta y/o un poder nutritivo más alto de los productos cosechados, una más alta capacidad de almacenamiento y/o elaborabilidad de los productos cosechados. 30 Ejemplos adicionales y resaltados especialmente de tales propiedades son una defensa aumentada de las plantas frente a plagas animales y microbianas, tal como frente a insectos, ácaros, hongos, bacterias y/o virus que son patógenos para las plantas, así como una tolerancia aumentada de las plantas frente a determinadas sustancias activas herbicidas. Como ejemplos de plantas transgénicas se mencionan las importantes 35 To the preferred plants or respectively varieties of transgenic plants 20 (obtained by genetic technology) to be treated according to the invention, belong all the plants that had been obtained by the genetic modification of a genetic material, which confers on these plants valuable properties ("features") especially advantageous. Examples of such properties are a better plant growth, an increased tolerance against high or low temperatures, an increased tolerance against dryness or water content or soil salts, an increased flowering yield, a facilitated harvest, an acceleration of maturation, higher yields of crops, a higher quality and / or a higher nutritional power of harvested products, a higher storage capacity and / or processability of harvested products. 30 Additional and especially highlighted examples of such properties are an increased defense of plants against animal and microbial pests, such as against insects, mites, fungi, bacteria and / or viruses that are pathogenic to plants, as well as increased tolerance. of plants against certain herbicidal active substances. Examples of transgenic plants are the important ones 35
plantas cultivadas, tales como cereales (trigo, arroz), maíz, soja, patata, algodón, colza así como plantas frutícolas (con las frutas manzanas, peras, frutas cítricas y uvas), teniendo que resaltarse especialmente maíz, soja, patata, algodón y colza. Como propiedades ("rasgos") se resaltan especialmente la defensa mejorada de las plantas frente a insectos por medio de unas toxinas que se forman en las plantas, en particular 5 las que son producidas en las plantas por el material genético procedente de Bacillus thuringiensis (p.ej. por los genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb y CryIF así como sus combinaciones) (en lo sucesivo "plantas Bt"). Como propiedades ("rasgos") se resaltan también especialmente la defensa aumentada de las plantas frente a hongos, bacterias y virus mediante resistencia 10 adquirida sistémica (SAR acrónimo de Systemische Akquirierte Resistenz), sistemina, fitoalexinas, elicitores así como genes de resistencia, y proteínas y toxinas expresadas de un modo correspondiente. Como propiedades ("rasgos") se resaltan especialmente además la tolerancia aumentada de las plantas frente a determinadas sustancias activas herbicidas, por ejemplo imidazolinonas, sulfonilureas, glifosato o fosfinotricina (p.ej. el gen 15 "PAT"). Los genes que confieren en cada caso las deseadas propiedades ("rasgos") se pueden presentar también en combinaciones entre ellos en las plantas transgénicas. Como ejemplos de "plantas Bt" se han de mencionar variedades de maíz, variedades de algodón, variedades de soja y variedades de patata, que se venden bajo las denominaciones comerciales YIELD GARD® (p.ej. maíz, algodón, soja), KnockOut® (p.ej. 20 maíz), StarLink® (p.ej. maíz), Bollgard® (algodón), Nucotn® (algodón) y NewLeaf® (patata). Como ejemplos de plantas tolerantes a los herbicidas se han de mencionar variedades de maíz, variedades de algodón y variedades de soja, que se venden bajo las denominaciones comerciales Roundup Ready® (tolerancia frente al glifosato p.ej. en maíz, algodón, soja), Liberty Link® (tolerancia frente a fosfinotricina, p.ej. en colza), IMI® 25 (tolerancia frente a imidazolinonas) y STS® (tolerancia frente a sulfonilureas, p.ej. en maíz). Como plantas resistentes a los herbicidas se han de mencionar también las variedades comercializadas bajo la denominación Clearfield®. Evidentemente, estas declaraciones son válidas también para las variedades de plantas que se desarrollen en el futuro o que lleguen al mercado en el futuro con estas propiedades genéticas ("ras-30 gos") o con unas propiedades genéticas que se desarrolladen en el futuro. cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed as well as fruit plants (with apples, pears, citrus fruits and grapes), especially corn, soybeans, potatoes, cotton and rapeseed. The properties ("traits") especially highlight the improved defense of plants against insects by means of toxins that are formed in plants, in particular those that are produced in plants by genetic material from Bacillus thuringiensis ( eg by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their combinations) (hereinafter "Bt plants"). The properties ("traits") also especially highlight the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (acronym SAR of Systemische Akquirierte Resistenz), systemin, phytoalexins, elicitors as well as resistance genes, and proteins and toxins expressed accordingly. The properties ("traits") especially highlight the increased tolerance of plants against certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (eg gene 15 "PAT"). The genes that confer in each case the desired properties ("traits") can also occur in combinations with each other in transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties, which are sold under the trade names YIELD GARD® (eg corn, cotton, soybeans), KnockOut ® (eg 20 corn), StarLink® (eg corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties, which are sold under the trade names Roundup Ready® (glyphosate tolerance for example in corn, cotton, soybeans) , Liberty Link® (tolerance to phosphinothricin, eg in rapeseed), IMI® 25 (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, eg in corn). As herbicide resistant plants, varieties marketed under the Clearfield® designation should also be mentioned. Obviously, these declarations are also valid for plant varieties that develop in the future or that reach the market in the future with these genetic properties ("ras-30 gos") or with genetic properties that develop in the future.
Las plantas reseñadas se pueden tratar de un modo especialmente ventajoso conforme al invento con los compuestos de la fórmula general I o respectivamente con las mezclas de sustancias activas conformes al invento, apareciendo, de manera adicional a la buena represión de las plantas de malezas, los efectos sinérgicos antes 35 The plants described can be treated in a particularly advantageous manner according to the invention with the compounds of the general formula I or respectively with the active substance mixtures according to the invention, appearing, in addition to the good repression of weed plants, synergistic effects before 35
mencionados con las plantas o variedades de plantas transgénicas. Los intervalos preferentes indicados en los casos de las sustancias activas o mezclas son válidos también para el tratamiento de estas plantas. Se ha de resaltar de un modo especial el tratamiento de las plantas con los compuestos o respectivamente con las mezclas que se exponen especialmente en el presente texto. 5 mentioned with the plants or varieties of transgenic plants. The preferred intervals indicated in the cases of the active substances or mixtures are also valid for the treatment of these plants. The treatment of plants with the compounds or respectively with the mixtures that are especially set forth herein should be highlighted in a special way. 5
La preparación y la utilización de las sustancias activas conformes al invento se desprenden de los siguientes Ejemplos. The preparation and use of the active substances according to the invention are derived from the following Examples.
Ejemplos de preparación: Preparation Examples:
Ejemplo 1-1 10 Example 1-1 10
Una mezcla de 2,80 g (8,43 mmol) de ácido 2,4-dicloro-3-[[(3-metil-2-oxo-1-imidazolidinil)-carbonil]-amino]-benzoico, de 0,945 g (8,43 mmol) de ciclohexano-1,3-diona, de 2,10 g (10,1 mmol) de diciclohexilcarbodiimida y 30 ml de acetonitrilo se agita durante 18 horas a la temperatura ambiente (aproximadamente 20ºC) y luego se filtra. El 15 material filtrado es reunido con 0,335 g (3,37 mmol) de cianuro de trimetilsililo y con 1,70 g (16,9 mmol) de trietilamina, la mezcla se agita durante 18 horas a la temperatura ambiente y a continuación se concentra por evaporación bajo presión reducida. El residuo se mezcla agitando con una solución acuosa al 10 % de carbonato de sodio y luego se agita con dietil-éter. Después de haber separado (y desechado) la fase orgánica, la 20 solución acuosa se acidifica con ácido clorhídrico concentrado, y el producto, que en este caso ha resultado en forma cristalina, se aísla mediante filtración con succión. A mixture of 2.80 g (8.43 mmol) of 2,4-dichloro-3 - [[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid, 0.945 g (8.43 mmol) of cyclohexane-1,3-dione, 2.10 g (10.1 mmol) of dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirred for 18 hours at room temperature (approximately 20 ° C) and then filtered . The filtrate is combined with 0.335 g (3.37 mmol) of trimethylsilyl cyanide and with 1.70 g (16.9 mmol) of triethylamine, the mixture is stirred for 18 hours at room temperature and then concentrated by evaporation under reduced pressure. The residue is mixed by stirring with a 10% aqueous solution of sodium carbonate and then stirred with diethyl ether. After having separated (and discarded) the organic phase, the aqueous solution is acidified with concentrated hydrochloric acid, and the product, which in this case has resulted in crystalline form, is isolated by suction filtration.
Se obtienen 2,20 g (49 % del rendimiento teórico) de N-[2,6-dicloro-3-[(2,6-dioxo-ciclohexil)-carbonil]-fenil]-3-metil-2-oxo-1-imidazolidina-carboxamida. 2.20 g (49% of theory) of N- [2,6-dichloro-3 - [(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -3-methyl-2-oxo- are obtained 1-imidazolidine-carboxamide.
logP (pH=2,3): 2,07. 25 logP (pH = 2.3): 2.07. 25
De una manera análoga a la del Ejemplo 1 así como de una manera correspondiente a la descripción general del procedimiento de preparación conforme al invento, se pueden preparar por ejemplo también los compuestos de la fórmula general (I) - o respectivamente de las fórmulas (I-1), (I-2) o (I-3) - que se exponen en las siguientes Tablas 1-1 hasta 1-5. 30 In a manner analogous to that of Example 1 as well as in a manner corresponding to the general description of the preparation process according to the invention, the compounds of the general formula (I) - or respectively of the formulas (I) can also be prepared for example. -1), (I-2) or (I-3) - which are set out in the following Tables 1-1 through 1-5. 30
Tabla 1-1: Ejemplos de los compuestos de la fórmula (I) en este caso R1 y R2 representan en cada caso hidrógeno e Y representa hidroxi Table 1-1: Examples of the compounds of the formula (I) in this case R1 and R2 in each case represent hydrogen and Y represents hydroxy
5 5
Tabla 1-2: Ejemplos de los compuestos de la fórmula (I) en este caso cada vez R1 representa metilo en posición 4, R2 representa metilo en posición 4 e Y representa hidroxi Table 1-2: Examples of the compounds of the formula (I) in this case each time R1 represents methyl in position 4, R2 represents methyl in position 4 and Y represents hydroxy
5 5
Tabla 1-3: Ejemplos de los compuestos de la fórmula (I) Table 1-3: Examples of the compounds of the formula (I)
En este caso cada vez R1 representa metilo en posición 5, R2 representa hidrógeno e Y representa hidroxi. In this case each time R1 represents methyl in position 5, R2 represents hydrogen and Y represents hydroxy.
5 5
Tabla 1-4: Ejemplos de los compuestos de la fórmula (I) Table 1-4: Examples of the compounds of the formula (I)
en este caso cada vez R1 representa metilo en posición 5, R2 representa metilo en posición 5 e Y representa hidroxi. 5 in this case each time R1 represents methyl in position 5, R2 represents methyl in position 5 and Y represents hydroxy. 5
Tabla 1-5: Ejemplos de los compuestos de la fórmula (I) Table 1-5: Examples of the compounds of the formula (I)
en este caso cada vez R1 y R2 representan una agrupación de metileno entre las posiciones 4 y 6 – "(4)-CH2CH2-(6)" e Y representa hidroxi. in this case each time R1 and R2 represent a grouping of methylene between positions 4 and 6 - "(4) -CH2CH2- (6)" and Y represents hydroxy.
5 5
La determinación de los valores de logP que se indican en las Tablas 1-1, 1-2, 1-3 y 1-4 se efectuó de acuerdo con la directiva del EEC 79/831 anejo V.A8, mediante una 5 HPLC (acrónimo de High Performance Liquid Chromatography = cromatografía en fase The determination of the logP values indicated in Tables 1-1, 1-2, 1-3 and 1-4 was carried out in accordance with EEC directive 79/831 annex V.A8, using a 5 HPLC ( Acronym for High Performance Liquid Chromatography = phase chromatography
liquida de alto rendimiento) en presencia de una columna con inversión de fases (C 18). Temperatura: 43ºC. high performance liquid) in the presence of a column with phase inversion (C 18). Temperature: 43ºC.
(a) Eluyentes para la determinación en la región ácida: ácido fosfórico acuoso al 0,1 %, acetonitrilo; gradiente lineal de desde 10 % de acetonitrilo hasta 90 % de acetonitrilo – los correspondientes resultados medidos se marcan con a) en la Tabla 1. 5 (a) Eluents for determination in the acid region: 0.1% aqueous phosphoric acid, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile - the corresponding measured results are marked with a) in Table 1. 5
(b) Eluyentes para la determinación en región neutra: solución acuosa 0,01 molar de un tampón de fosfato, acetonitrilo; gradiente lineal de desde 10 % de acetonitrilo hasta 90 % de acetonitrilo – los correspondientes resultados medidos se marcan con b) en la Tabla 1. (b) Eluents for neutral region determination: 0.01 molar aqueous solution of a phosphate buffer, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile - the corresponding measured results are marked with b) in Table 1.
La calibración se efectuó con alcan-2-onas no ramificadas (con 3 a 16 átomos de carbono), cuyos valores de logP son conocidos (la determinación de los valores de logP 10 se efectúa con ayuda de los períodos de tiempo de retención mediante interpolación lineal entre dos alcanonas consecutivas). The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (the determination of the logP 10 values is carried out with the help of retention periods by interpolation linear between two consecutive ranges).
Los valores de lambda-max se determinaron con ayuda de los espectros de UV de desde 200 nm hasta 400 nm en los máximos de las señales cromatográficas. Lambda-max values were determined using the UV spectra from 200 nm to 400 nm at the maximum of the chromatographic signals.
15 fifteen
Sustancias de partida de la fórmula (III) Starting substances of the formula (III)
Ejemplo (III-1) Example (III-1)
Una mezcla de 11,3 g (32,9 mmol) del éster metílico de ácido 2,4-dicloro-3-[[(3-metil-2-oxo-1-imidazolidinil)-carbonil]-amino]-benzoico, de 50 ml de agua, de 50 ml de 20 tetrahidrofurano y de 1,3 g de hidróxido de sodio se agita durante 18 horas a la temperatura ambiente (aproximadamente 20ºC) y a continuación se concentra por evaporación bajo presión reducida hasta dejar aproximadamente la mitad del volumen. Luego se sacude con dietil-éter, la fase orgánica se separa (y desecha) y la fase acuosa se acidifica con ácido clorhídrico concentrado. El producto que en este caso ha resultado 25 en forma cristalina se aísla mediante filtración con succión. A mixture of 11.3 g (32.9 mmol) of the 2,4-dichloro-3 - [[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid methyl ester, 50 ml of water, 50 ml of 20 tetrahydrofuran and 1.3 g of sodium hydroxide is stirred for 18 hours at room temperature (approximately 20 ° C) and then concentrated by evaporation under reduced pressure until approximately half of the volume. It is then shaken with diethyl ether, the organic phase is separated (and discarded) and the aqueous phase is acidified with concentrated hydrochloric acid. The product that in this case has resulted in crystalline form is isolated by suction filtration.
Se obtienen 9,1 g (81,5 % del rendimiento teórico) de ácido 2,4-dicloro-3-[[(3-metil-2-oxo-1-imidazolidinil)-carbonil]-amino]-benzoico. 9.1 g (81.5% of theory) of 2,4-dichloro-3 - [[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid are obtained.
logP (pH = 2,3): 1,35 logP (pH = 2.3): 1.35
30 30
Análogamente al Ejemplo (III-1) se pueden preparar por ejemplo también los compuestos de la fórmula general (III) que se exponen en la Tabla 2 siguiente. Analogously to Example (III-1), for example, the compounds of the general formula (III) set forth in Table 2 below can also be prepared.
5 5
Tabla 2: Ejemplos de los compuestos de la fórmula (III) Table 2: Examples of the compounds of the formula (III)
Sustancias de partida de la fórmula (IIIa) Starting substances of the formula (IIIa)
Ejemplo (IIIa-1) Example (IIIa-1)
Una mezcla de 12,3 g (50 mmol) del éster metílico de ácido 2,4-dicloro-3-isocianato-benzoico, de 5,0 g (50 mmol) de 1-metil-2-oxo-imidazolina, de algunas gotas 5 de trietilamina y de 100 ml de acetonitrilo se agita durante 18 horas a la temperatura ambiente (aproximadamente 20ºC) y a continuación se concentra por evaporación bajo presión reducida. El residuo se digiere luego con dietil-éter y el producto cristalino se aísla mediante filtración con succión. A mixture of 12.3 g (50 mmol) of the 2,4-dichloro-3-isocyanate benzoic acid methyl ester of 5.0 g (50 mmol) of 1-methyl-2-oxo-imidazoline, of some 5 drops of triethylamine and 100 ml of acetonitrile are stirred for 18 hours at room temperature (approximately 20 ° C) and then concentrated by evaporation under reduced pressure. The residue is then digested with diethyl ether and the crystalline product is isolated by suction filtration.
Se obtienen 11,4 g (60 % del rendimiento teórico) del éster metílico de ácido 2,4-dicloro-10 3-[[(3-metil-2-oxo-1-imidazolidinil)-carbonil]-amino]-benzoico, 11.4 g (60% of theory) of 2,4-dichloro-10 3 - [[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid methyl ester are obtained ,
logP (pH=2,3): 1,94. logP (pH = 2.3): 1.94.
Análogamente al Ejemplo (IIIa-1) se pueden preparar por ejemplo también los compuestos de la fórmula general (III) que se exponen en la siguiente Tabla 3. Analogously to Example (IIIa-1), for example, the compounds of the general formula (III) set forth in the following Table 3 can also be prepared.
15 fifteen
Tabla 3: Ejemplos de los compuestos de la fórmula (IIIa) Table 3: Examples of the compounds of the formula (IIIa)
Ejemplos de aplicaciones: Examples of applications:
Ejemplo A Example A
Ensayo antes del brote Trial before the outbreak
Disolvente: 5 partes en peso de acetona 5 Solvent: 5 parts by weight of acetone 5
Emulsionante: 1 parte en peso de un alquilaril-poliglicol-éter Emulsifier: 1 part by weight of an alkylaryl polyglycol ether
Para la preparación de una formulación conveniente de una sustancia activa, se mezcla 1 parte en peso de una sustancia activa con la cantidad indicada de un disolvente, se añade la cantidad indicada de un emulsionante y se diluye el concentrado con agua hasta llegar a la concentración deseada. 10 For the preparation of a convenient formulation of an active substance, 1 part by weight of an active substance is mixed with the indicated amount of a solvent, the indicated amount of an emulsifier is added and the concentrate is diluted with water until it reaches concentration desired. 10
Unas semillas de las plantas sometidas a ensayo se siembran en un suelo normal. Después de 24 horas, el suelo es rociado con la formulación de sustancia activa, de tal manera que se esparce la cantidad en cada caso deseada de la sustancia activa por Seeds of the plants under test are sown in normal soil. After 24 hours, the soil is sprayed with the active substance formulation, so that the amount in each desired case of the active substance is spread by
unidad de superficie. La concentración de la sustancia activa en el caldo para proyectar se escoge de tal manera que en 1.000 litros de agua por hectárea se esparza la cantidad en cada caso deseada de la sustancia activa. surface unit. The concentration of the active substance in the broth to project is chosen in such a way that in 1,000 liters of water per hectare the amount in each desired case of the active substance is spread.
Después de tres semanas se valora el grado de daño para las plantas en % de daño en comparación con el desarrollo del testigo sin tratar. Significan: 5 After three weeks the degree of damage to the plants is assessed in% damage compared to the development of the untreated control. They mean: 5
0 % = ningún efecto (como el testigo sin tratar) 0% = no effect (as the untreated control)
100 % = destrucción total. 100% = total destruction.
En este ensayo, por ejemplo los compuestos de acuerdo con los Ejemplos de preparación 1-1, 1-2, 1-4 y 1-5 muestran una buena compatibilidad frente a plantas cultivadas, tales como p.ej. maíz y un fuerte efecto contra malezas. 10 In this test, for example the compounds according to Preparation Examples 1-1, 1-2, 1-4 and 1-5 show good compatibility against cultivated plants, such as corn and strong effect. Against weeds. 10
Ejemplo B: Example B:
Ensayo después del brote Trial after the outbreak
Disolvente: 5 partes en peso de acetona Solvent: 5 parts by weight of acetone
Emulsionante: 1 parte en peso de un alquilaril-poliglicol-éter 15 Emulsifier: 1 part by weight of an alkylaryl-polyglycol-ether 15
Para la preparación de una formulación conveniente de la sustancia activa, se mezcla 1 parte en peso de una sustancia activa con la cantidad indicada de un disolvente, se añade la cantidad indicada de un emulsionante y el concentrado se diluye con agua hasta llegar a la concentración deseada. For the preparation of a suitable formulation of the active substance, 1 part by weight of an active substance is mixed with the indicated amount of a solvent, the indicated amount of an emulsifier is added and the concentrate is diluted with water until it reaches concentration desired.
Con la formulación de sustancia activa se rocían las plantas sometidas a ensayo, 20 que tienen una altura de 5 a 15 cm, de tal manera que se esparzan las cantidades en cada caso deseadas de la sustancia activa por unidad de superficie. La concentración de la sustancia activa en el caldo para proyectar se escoge de tal manera que en 1.000 litros de agua por hectárea se esparza la cantidad en cada caso deseada de la sustancia activa. 25 With the active substance formulation, the plants under test are sprayed, 20 having a height of 5 to 15 cm, such that the desired quantities of the active substance per unit area are spread in each case. The concentration of the active substance in the broth to project is chosen in such a way that in 1,000 liters of water per hectare the amount in each desired case of the active substance is spread. 25
Después de tres semanas se valora el grado de daño para las plantas en % de daño en comparación con el desarrollo del testigo sin tratar. After three weeks the degree of damage to the plants is assessed in% damage compared to the development of the untreated control.
Significan: They mean:
0 % = ningún efecto (como el testigo sin tratar) 0% = no effect (as the untreated control)
100 % = destrucción total. 30 100% = total destruction. 30
En este ensayo, por ejemplo los compuestos de acuerdo con los Ejemplos de preparación 1, 2, 4 muestran, junto con una buena compatibilidad frente a plantas cultivadas, un fuerte efecto contra malezas y malas hierbas. In this test, for example the compounds according to Preparation Examples 1, 2, 4 show, together with a good compatibility against cultivated plants, a strong effect against weeds and weeds.
Ensayo en arroz sembrado (en invernadero) Test on seeded rice (in greenhouse)
Disolvente: 5 partes en peso de acetona Solvent: 5 parts by weight of acetone
Emulsionante: 1 parte en peso de un alquilaril-poliglicol-éter 5 Emulsifier: 1 part by weight of an alkylaryl-polyglycol-ether 5
Para la preparación de una conveniente formulación para proyectar se mezcla 1 parte en peso de una sustancia activa con la cantidad indicada del disolvente y del emulsionante, y por mezcladura con agua se diluye hasta la concentración desea. For the preparation of a suitable formulation for projecting, 1 part by weight of an active substance is mixed with the indicated amount of solvent and emulsifier, and by mixing with water it is diluted to the desired concentration.
Unos recipientes para plantas (con el tamaño: 20 cm x 20 cm x 9 cm; superficie 1/200 Ar) se llenan con un suelo procedente de un campo de arroz. Las semillas de arroz 10 y de malezas se siembran en la tierra mantenida en estado húmedo. En el estadio de 1,5 – 2 hojas del arroz se esparce la formulación diluida de sustancia activa en forma de una rociadura (tratamiento de las hojas). Containers for plants (with the size: 20 cm x 20 cm x 9 cm; surface 1/200 Ar) are filled with a soil from a rice field. Rice seeds 10 and weeds are sown in the soil kept in a wet state. The diluted formulation of active substance in the form of a spray (leaf treatment) is spread in the 1.5-2 leaf stage of the rice.
Un día después del tratamiento, los recipientes del ensayo se anegan hasta llegar a una profundidad del agua de 3 cm. A continuación las tandas de ensayo se mantienen 15 en condiciones de inundación (profundidad del agua 3 cm). One day after treatment, the test vessels are flooded until they reach a water depth of 3 cm. Then the test batches are kept 15 in flood conditions (water depth 3 cm).
4 Semanas después de la aplicación de la sustancia activa se valora el grado de daño para las plantas en % de daño (o respectivamente de efecto contra malezas) en comparación con un testigo sin tratar. 4 Weeks after the application of the active substance, the degree of damage to the plants is assessed in% damage (or respectively of effect against weeds) compared to an untreated control.
Significan: 20 They mean: 20
0 % = ningún efecto (como el testigo sin tratar) 0% = no effect (as the untreated control)
100 % = destrucción total. 100% = total destruction.
En este ensayo, por ejemplo los compuestos de acuerdo con los Ejemplos de preparación 1, 2, 4 muestran, junto con una buena compatibilidad frente a las plantas cultivadas, un fuerte efecto contra malezas 25 In this test, for example the compounds according to Preparation Examples 1, 2, 4 show, together with a good compatibility against cultivated plants, a strong effect against weeds.
Claims (8)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10123887 | 2001-05-16 | ||
DE10123887 | 2001-05-16 | ||
DE10138576 | 2001-08-06 | ||
DE10138576A DE10138576A1 (en) | 2001-05-16 | 2001-08-06 | New substituted benzoylcyclohexenone derivatives useful as antimicrobials and herbicides, especially for selective application in transgenic crops |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2349257T3 true ES2349257T3 (en) | 2010-12-29 |
Family
ID=7685037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES02730231T Expired - Lifetime ES2349257T3 (en) | 2001-05-16 | 2002-05-03 | BENZOILCICLOHEXENONAS REPLACED AND ITS USE AS HERBICITY AGENTS. |
Country Status (6)
Country | Link |
---|---|
KR (1) | KR20040007541A (en) |
AR (1) | AR034319A1 (en) |
AT (1) | ATE476421T1 (en) |
DE (2) | DE10138576A1 (en) |
ES (1) | ES2349257T3 (en) |
UA (1) | UA77415C2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100881137B1 (en) | 2007-08-07 | 2009-02-02 | 충남대학교산학협력단 | New pig pheromonal compounds, their preparation method and a composite for estrus induction |
-
2001
- 2001-08-06 DE DE10138576A patent/DE10138576A1/en not_active Withdrawn
-
2002
- 2002-03-05 UA UA20031211616A patent/UA77415C2/en unknown
- 2002-04-29 AR ARP020101568A patent/AR034319A1/en unknown
- 2002-05-03 ES ES02730231T patent/ES2349257T3/en not_active Expired - Lifetime
- 2002-05-03 AT AT02730231T patent/ATE476421T1/en active
- 2002-05-03 KR KR10-2003-7014448A patent/KR20040007541A/en not_active Application Discontinuation
- 2002-05-03 DE DE50214569T patent/DE50214569D1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ATE476421T1 (en) | 2010-08-15 |
UA77415C2 (en) | 2006-12-15 |
DE50214569D1 (en) | 2010-09-16 |
DE10138576A1 (en) | 2002-11-21 |
AR034319A1 (en) | 2004-02-18 |
KR20040007541A (en) | 2004-01-24 |
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