MXPA99000957A - Substituted p-trifluoromethylphenyluracils - Google Patents

Abstract

The invention concerns new substituted p-trifluoromethylphenyluracils having general formula (I) wherein R1 stands for hydrogen, cyano or halogen, R2 stands for the grouping A1-A2-A3, R3 stands for hydrogen, halogen or alkyl optionally substituted by halogen, R4 stands for alkyl optionally substituted by halogen, and R5 stands for hydrogen, amino or alkyl optionally substituted by hydroxy, cyano, halogen or alkoxy, the methods for the production thereof and their use as herbicides.

Description

P - SUBSTITUTE TRIFLUMETHYLENTILATED.

Field of the invention The present invention relates to novel substituted p-trifluoridephenyluracils, processes for their preparation and their use as herbicides.

Description of the prior art It is known that certain substituted p-trifluoromethylphenyl-uracils, such as for example the compound 3- (3-chloro-4-trifluoromethyl-phenyl) -6- (2,6-difluoro-phenyl) - [H, 3H] -pyrimidine -2,4-dione have pesticidal properties, that is to say they are active against certain animal pests, especially against insects and mites (see JP 05025142, cited in Chem. Abstracts 119: 117269). However, nothing has been disclosed about a herbicidal activity of these compounds.

Detailed description of the invention It has now been found that the new substituted p-tri-fluoro-methylphenyluracils of the formula REF .: 29273 general (I) wherein R1 signifies hydrogen, cyano, or halogen, R2 signifies the grouping A1-A2-A3, where A1 signifies a single bond, means O, S, -SO-, -S02-, -CO- or signifies the grouping - N-A4-, where A4 means hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A1 further means alkanediyl, alkenodiyl, azaalkenodiyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or phenylene substituted respectively by halogen , A2 means a single bond, means O, S, -SO-, -S02-, -CO- or the group -N-A4-, where A4 means hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A2 also means alkanediyl, alkenodiyl, azaalkenodiyl, alkynediyl, cycloalkanediyl, cycloalkenodiyl or phenyl, each optionally substituted by halogen, A3 means hydrogen, hydroxy, mercapto, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl or, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl substituted, where appropriate, by halogen or by alkoxy, means alkenyl, alkenyloxy, alkenylamino, alkylidene alkenyloxycarbonyl, alkynyl, alkynyloxy, alkylamino or alkynyloxycarbonyl respectively substituted, if appropriate, by halogen, means cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl respectively substituted, if appropriate, by halogen, cyano, carboxy, alkyl and / or or by alkoxycarbonyl, or means aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl respectively substituted, where appropriate, by nitro, by cyano, by carboxy, by halogen, by alkyl, by haloalkyl, by alkoxy, by haloalkoxy and / or by alkoxy-carbonyl or, A3 further denotes pyrrolyl, piperazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazoalkyl , thiazoalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furyalkoxy, hydrogenated, if appropriate, wholly or in part, respectively, means perhydropyranylalkoxy or pyridylalkoxy, R 3 is hydrogen, halogen or alkyl optionally substituted by halogen, R 4 is alkyl substituted, if appropriate, by halogen, and R 5 means hydrogen, amino or alkyl optionally substituted by hydroxy, by cyano, by halogen or by alkoxy. The new substituted p-trifluoromethylphenyluracils of the general formula (I) are obtained, if aminoalkenoic acid esters of the general formula (II) are reacted wherein R3 and R4 have the meanings indicated above R means alkyl, aryl or arylalkyl, with p-trifluoromethylphenyl isocyanates of the general formula (III) wherein R1 and R2 have the meanings indicated above, or with p-trifluoromethylphenylurethanes (p-trifluoromethylphenylcarbates) of the general formula (IV) wherein R1 and R2 have the meanings indicated above and R means alkyl, aryl or arylalkyl, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and optionally performed on the compounds thus obtained, of the formula (I), in the scope of the definitions of the above substituents, other transformations according to usual methods. The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the definitions of the above substituents, for example by means of conventional electrophilic or nucleophilic substitution reactions (for example R2: F? OH , SH, NH2 / 0CH3, SC2H5, NHC3H7-i, NHS02CH3, R5: H? NH2, CH3), see also the preparation examples. The novel substituted p-trifluoromethylphenyluracils of the general formula (I) are characterized by a potent herbicidal activity. They also show good compatibility with important crop plants, such as, for example, wheat, barley and corn. In the definitions the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl - even in combination with heteroatoms, such as in alkoxy or alkylthio - are respectively straight-chain or branched chain. In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially fluorine or chlorine. The subject of the invention are preferably the compounds of the formula (I), in which R 1 signifies hydrogen, cyano, fluorine, chlorine or bromine, R 2 signifies the grouping A1-A2-A3, where A1 means a single bond, means O , S, -SO-, -S02-, -CO- or the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms carbon or phenyl sulfonyl, A1 further means alkanediyl with the β carbon atoms alkenodiyl with 2 to β carbon atoms, alkenodiyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenediyl with 3 to 6 carbon atoms or phenylene substituted respectively by fluorine or by chlorine, A2 means a single bond, means 0, S, -SO-, -S02-, -CO- or means the group -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonyl, A2 also means alkanediyl with the β carbon atoms, alkenodiyl with 2 to 6 atoms carbon, alkynediyl with 2 to 6 carbon atoms, cycloalkane ilo with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene substituted respectively where appropriate by fluorine or chlorine, A3 means hydrogen, hydroxy, mercapto, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, Carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl with respectively the β carbon atoms in the alkyl groups, respectively substituted given by fluorine, chlorine, bromine, or alkoxy with 1 to 4 carbon atoms, means alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl with 2 to 6 carbon atoms in the groups alkenyl, alkylidene or alkynyl, respectively substituted, if appropriate, by fluorine, chlorine or bromine, means cycloalkyl, cycloa alkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl with 3 to 6 carbon atoms in the cycloalkyl groups respectivelyand, optionally, from 1 to 4 carbon atoms in the alkyl groups, optionally substituted, respectively, by fluorine, chlorine, bromine, cyano, carboxy, alkyl with 1 to 4 carbon atoms and / or alkoxy carbonyl with 1 to 4 carbon atoms, or means phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl, phenylalkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or phenylalkoxycarbonyl with 1 to 4 carbon atoms, respectively substituted by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by h halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy having 1 to 4 carbon atoms and / or alkoxycarbonyl having 1 to 4 carbon atoms means (respectively, totally or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-alkyl with 1 to 4 carbon atoms, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl-alkyl with 1 to 4 carbon atoms, isoxazole-C 1 -C 4 -alkyl, thiazole-C 1 -C 4 -alkyl pyridinyl-C 1 -C 4 -alkyl, pyrimidinyl-C 1 -C 4 -alkyl, pyrazolylmethoxy , furylmethoxy, means perhydropyranylmethoxy or pyridylmethoxy, R3 means hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine and / or chlorine, R4 means alkyl having 1 to 4 carbon atoms substituted case given by fluorine and / or by chlorine, and R5 means hydrogen, amino or alkyl having 1 to 4 carbon atoms, optionally substituted by hydroxy, by cyano, by fluorine, by chlorine, or by alkoxy with 1 to 4 carbon . The invention relates especially to the compounds of the formula (1), in which R 1 signifies hydrogen, fluorine or chlorine, R 2 signifies the grouping A1-A2-A3, where A1 means a single bond, means 0, S, -SO -, -S02-, CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl , A1 further means methylene, ethane-1, l-diyl, ethane-1,2-diyl, propane-1, l-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1, 2-diyl, propene-1,3-diyl, etino-1,2-diyl or propino-1,3-diyl, A2 means a single bond, means 0, S, -SO- , S02-, -CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or 1-propylsulfonyl or phenylsulfonyl, 2 further means methylene, ethane-1, 1-diyl, ethane-1,2-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-1,3-diyl, ethene-l-2-diyl, propene-1,2-diyl, propene-1,3-diyl, etino-1,2-diyl or propino- 1,3-diyl means hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluoro, chloro, bromo, means methyl, ethyl, n- or 1-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or 1-propylsulfinyl, methylsulfonyl, ethylsulphonyl, n- or 1-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl substituted respectively where appropriate by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenam ino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, Butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butiniloxicarbonilo substituted especially optionally fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, ciciohexilmetilo, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexyl ethoxycarbonyl respectively substituted, where appropriate, by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or by ethoxycarbonyl, or means phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl respectively substituted, where appropriate, by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl, p or trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by difluoromethoxy, by trifluoromethoxy, by methoxycarbonyl and / or by ethoxycarbonyl, means (respectively, if any partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienyl ethyl, oxazolyl ethyl, isoxazolylmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R3 signifies hydrogen, fluorine, chlorine, bromine or means methyl or ethyl substituted respectively by fluorine and / or by chlorine, where R.sup.4 is methyl or ethyl substituted respectively by fluorine and / or chlorine, and R.sup.5 is hydrogen, amino or methyl or ethyl substituted, where appropriate, by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy. -j_5 The definitions of the residues indicated above in a general manner or indicated in preferred ranges are valid both for the final products of the formula (I) and, correspondingly, also for the starting materials or for the necessary intermediate products respectively for obtaining. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated. Examples of compounds of formula (I) according to the invention have been indicated in the following groups.

Group 1 In this case, R2 has, for example, the meanings indicated in the following list: hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, n-, i-, s- or t-pentyl, difluoromethyl, trifluoromethyl, chloro-difluoromethyl, fluorochloromethyl, fluoroethyl, chloroethyl, chlorofluoroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, tetrafluoroethyl, chlorotrifluoroethyl, pentafluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, dichloropropyl, trifluoropropyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl, methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, methoxycarbonyl bonylethyl, ethoxycarbonylethyl, propoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylpropyl, propoxycarbonylpropyl or, l-propene-3-yl (allyl), 3-methyl-l-propene-3-yl, 2-butene-4-yl (crotonyl), l-propynyl-3-yl (propargyl), 3-methyl -l-propin-3-yl, 2-butin-4-yl, cyclopropyl, cyanocyclopropyl, carboxycyclopropyl, difluorocyclopropyl, dichlorocyclopropyl, methylcyclopropyl, methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl, cyclobutyl, cyanocyclobutyl, carboxycyclobutyl, difluorocyclobutyl, trifluorocyclobutyl, tetrafluorocyclobutyl , clorotriflúorciclobutilo, methylcyclobutyl, cyclopentyl, cyano-cyclopentyl, carboxycyclopentyl, flúorciclopentilo, chlorocyclopentyl, diflúorciclopentilo, dichlorocyclopentyl, methylcyclopentyl, metoxicarbonilciclopentilo, etoxicarbonilciclopentilo, cyclohexyl, cyanocyclohexyl, carboxycyclohexyl, flúorciclohexilo, chlorocyclohexyl, diflúorciclohexilo, dichlorocyclohexyl, methylcyclohexyl, triflúormetilciclohexilo, metoxicarbonilciclohexilo, etoxicarboniIciclohexilo, cyclopropylmethyl , difluorocyclopropylmethyl, dichlorocyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanocyclohexylmethyl, carboxycyclohexylmethyl, fluorocyclohexylmethyl, chlorocyclohexylmethyl, methylcyclohexylmethyl, trifluoromethylcyclohexylmethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, so-butoxy, n-, i -, s- or t-pentoxy, difluoro-methoxy, trifluoromethoxy, chlorodifluoromethoxy, flúordiclo-rometoxi, fluoroethoxy, chloro-ethoxy, cloroflúoretoxi, difluoroethoxy, dichloroethoxy, trifluoroethoxy, trichloroethoxy, ciorodiflúoretoxi, tetrafluoroethoxy, clorotriflúoretoxi, pentafluoroethoxy, fluoropropoxy, chloropropoxy, diflúorpropoxi , dichloropropoxy, triflúorpropoxi, cyanomethoxy, cyanoethoxy, cyanopropoxy, cyanobutoxy, carboxymethoxy, carboxyethoxy, carboxypropoxy, carboxybutoxy, methoxymethoxy, ethoxymethoxy, propoxymethoxy, methoxyethoxy, ethoxyethoxy, propoxyethoxy, methoxypropoxy, ethoxypropoxy, propoxypropoxy, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propoxycarbonyl ethoxy, metoxicarboniloetoxi, ethoxycarbonylethoxy, propoxycarbonylethoxy, methoxy rbonylpropoxy, ethoxycarbonylpropoxy, propoxycarbonylpropoxy, 1-propen-3-yl-oxy (allyloxy), l-methyl-l-propen-3-yl-oxy, 2-buten-4-yl-oxy (crotonyloxy), l-propynyl 3-il-oxy, (propargyloxy), 3-methyl-i-propy-3-yl-oxy, 2-butyn-4-yl-oxy, cyclopropyloxy, cyanocyclopropyloxy, carboxycyclopropyloxy, difluorocyclopropyloxy, dichlorocyclopropyloxy, methylcyclopropyloxy, methoxycarbonylcyclopropyloxy, ethoxycarbonyl-cyclopropyloxy, cyclobutyloxy, cyanocyclobutyloxy, carboxycyclobutyloxy, diflúorciclobutiloxi, triflúorciclobutiloxi, tetraflúorciclobutiloxi, clorotriflúorciclobutiloxi, metilciclobutiloxi, cyclopentyloxy, cianociclopentiloxi, carboxiciclopentiloxi, flúorciclopentiloxi, clorociclopentiloxi, diflúorciclopentiloxi, diclorociclopentiloxi, methylcyclopentyloxy, metoxicarbonilciclopentiloxi, etoxicarbonilciclopentiloxi, cyclohexyloxy, cianociclohexiloxi, carboxiciclohexiloxi, flúorciclohexiloxi, clorociclohexiloxi, diflúorciclohexiloxi, diclorociclohexiloxi, methylcyclohexyloxy, triflúormetilciclohexiloxi, metoxicarbonilciclohexiloxi, Etoxicarbonilciclohexiloxi, cyclopropylmethoxy, diflúorciclopropilmetoxi, diclorociclopropilmetoxi, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cianociclohexilmetoxi, carboxiciclohexilmetoxi, flúorciclohexilmetoxi, clorociclohexilmetoxi, metilciclohexilmetoxi, triflúormetilciclohexilmetoxi, methylthio, ethylthio, n- or i-propylthio, n-, i-, or t-butylthio, n -, i, s- or t-pentylthio, difluoromethylthio, trifluoro ethylthio, chlorodifluoromethylthio, flúordiclorometiltio, flúoretiltio, chloroethylthio, cloroflúoretiltio, diflúoretiltio, dicloroetiltio, trifluoromethylthio, trichloroethylthio, clorodiflúoretiltio, tetraflúoretiltio, clorotriflúoretiltio, pentaflúoretiltio, flúorpropiltio, chloropropylthio, diflúorpropiltio, dicloropropiltio, trifluoropropylthio, cyanomethylthio, cyanoethylthio, cyanopropylthio, cyanobutylthio, carboxymethylthio, carboxyethylthio, carboxypropylthio, carboxybutylthio, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, propoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbon Ilethylthio, propoxycarbonylethylthio, methoxycarbonylpropylthio, ethoxycarbonylpropylthio, propoxycarbonylpropythio, l-propen-3-ylthio (allylthio), 3-methyl-l-propen-3-yl-thio, 2-buten-4-yl-thio, l-propin-3-yl-thio (propargylthio), 3-methyl-l-propin-3-ylthio -, 2-butyn-4-ylthio, cyclopropylthio, cianociclopropiltio, carboxiciclopropiltio, diflúorciclopropiltio, diclorociclopropiltio, metiIciclopropiltio, metoxicarboniIciclopropiltio, etoxicarboniIciclopropiltio, cyclobutylthio, cianociclobutiltio, carboxiciclobutiltio, diflúorciclobutiltio, triflúorciclobutiltio, tetraflúorciclobutiltio, clorotriflúorciclobutiltio, metilciclobutiltio, cyclopentylthio, cianociclopentiltio, carboxiciclopentiltio, flúorciclopentiltio, clorociclopentiltio, diflúorciclopentiltio, diclorociclopentiltio, metilciclopentiltio, metoxicarbonilciclopentiltio, etoxicarbonilciclopentiltio, cyclohexylthio, cianociclohexiltio, carboxy-cyclohexylthio, flúorciclohexiltio, clorociclohexiltio, diflúorciclohexiltio, diclorociclohexiltio, metilciclohexiltio, triflúormetilciclohexiltio, metoxicarbonilciclohexiltio, etoxicarbonilciclohexiltio, cyclopropylmethylthio, difluoro cyclopropylmethylthio, dichlorocyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyanocyclohexylmethylthio, carboxycyclohexylmethylthio, fluorocyclohexylmethylthio, chlorocyclohexylthioethyl, methyl-cyclohexylmethylthio, methylamino, ethylamino, n- or i-propyl-amino, n-, i-, s- or t-butylamino, n -, i-, s- or t-pentyl-ano, cyanomethylamino, cyanoethylamino, cyanopropylamino, cyanobutylamino, carboxymethylamino, carboxyethylamino, carboxy-propylamino, carboxybutylamino, methoxymethylamino, ethoxymethylamino, propoxymethylamino, methoxyethylamino, ethoxyethylamino, propoxyethylamino, methoxypropylamino, ethoxypropylamino, propoxypropylamino , methoxycarbonylmethylamino, ethoxycarbonylmethylamino, propoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylethylamino, propoxycarbonylethylamino, methoxycarbonylpropylamino, ethoxycarbonylpropylamino, propoxycarbonylpropylamino, l-propen-3-yl-amino (allylamino), 3-methyl-l-propen-3-ylamino, 2-bu-ten-4-yl-amino (crotonylamino), l-propyn-3-yl-amino (propargylamino), 3-methyl-l- propin-3-yl-amino, 2-butin-4-yl-amino, cyclopropylamino, cyanocyclopropylamino, carboxycyclopropylamino, difluorocyclopropylamino, dichlorocyclopropylamino, methy1-cyclopropylamino, methoxycarbonyl-cyclopropylamino, ethoxycarbonylcyclopropylamino, cyclobutylamino, cyanocyclobutylamino, carboxycyclobutylamino, difluorocyclobutylamino, trifluorocyclobutylamino, tetra- flúorciclobutilamino, chloro-triflúorciclobutilamino, methylcyclobutylamino, cyclopentylamino, cianociclopentil-amino, carboxiciclopentilamino, flúorciclopentilamino, clorociclopentilamino, diflúorciclopentilamino, diclorociclopentilamino, metiIciclopentilamino, metoxicarbonilciclopentilamino, ethoxy-carbonilciclopentilamino, cyclohexylamino, cianociclohexilamino, carboxiciclohexilamino, flúorciclohexilamino, clorociclohexilamino, diflúorciclohexilamino, diclorociclohexilamino, methylcyclohexylamino, triflúormetilciclohexilamino, metoxicarbonilciclohexilamino, etoxicarbonilciclohexilamino, cyclopropylmethyl, diflúorciclopropilmetilamino, di-clorociclopropilmetilamino, ino ciclobutilmetila, cyclopentylmethylamino, cyclohexylmethylamino, cianociclohexilmetilamino, carboxiciclohexilmetilamino, flúorciclohexilmetilamino, clorociclohexilmetilamino, metiIciclohexilmetilamino, trifluoro-metilciclohexilmetilamino, phenyl, cyanophenyl, carboxyphenyl, nitrophenyl, fluoro-phenyl, chlorophenyl, bromophenyl , methylphenyl, trifluoromethylphenyl, methoxyphenyl, diflúormetoxifenilo, trifluoromethoxyphenyl, methoxycarbonylphenyl, ethoxycarbonylphenyl, benzyl, cyanobenzyl, carboxybenzyl, fluorobenzyl, chlorobenzyl, methylbenzyl, trifluoromethylbenzyl, methoxybenzyl, diflúormetoxibencilo, triflúormetoxibencilo, methoxycarbonylbenzyl, ethoxycarbonylbenzyl, phenylethyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl , tetrahydrothienyl, oxetanyl, oxazolyl, isoxazolyl, pheno xi, cyanophenoxy, carboxyphenoxy, nitrophenoxy, fluorophenoxy, chlorophenoxy, bromophenoxy, methylphenoxy, trifluoromethylphenoxy, methoxyphenoxy, Diflúormetoxifenoxi, triflúormetoxifenoxi, methoxycarbonylphenoxy, ethoxycarbonylphenoxy, benzyloxy, cyanobenzyloxy, carboxybenzyloxy, fluorobenzyloxy, chlorobenzyloxy, methylbenzyloxy, trifluoromethylbenzyloxy, methoxybenzyloxy, etoxibenciloxi difluoro, triflúormetoxibenciloxi, methoxycarbonylbenzyloxy, etoxicarbonilbenciloxi, phenylethoxy, furyloxy, furylmethoxy, tetrahydrofuryloxy, tetrahidrofurilmetoxi, thienyloxy, tetrahidrotieniloxi, oxetanyloxy, oxazolyloxy, isoxazolyloxy, phenylthio, cyanophenylthio, carboxyphenylthio, nitrophenylthio, fluorophenylthio, chlorophenylthio, bromophenylthio, methylphenylthio, triflúormetilfeniltio, methoxyphenylthio, diflúormetoxifeniltio, triflúormetoxifeniltio, methoxycarbonylphenylthio, etoxicarbonilfeniltio, benzylthio, cianobenciltio, carboxibenciltio, flúorbenciltio, clorobenciltio, methylbenzylthio, triflúormetilbenciltio, methoxybenzylthio, diflúormetoxibenciltio, trifluoromethoxybenzylthio, methoxycarbonylbenzylthio, ethoxycarbonylbenzylthio, phenyl ethylthio, phenylamino, cyano phenylamino, carboxyphenylamino, nitrophenylamino, fluorophenylamino, chlorophenylamino, bro-mofenil-amino, methylphenylamino, triflúormetilfenilamino, methoxyphenylamino, diflúormetoxifenilamino, triflúormeto-xifenilamino, methoxycarbonylphenylamino, amino, amino, cianobencilamino, carboxybenzylamino, fluorobenzylamino, chlorobenzylamino, methylbenzylamino, triflúormetilbencilamino, methoxybenzylamino, diflúormetoxibencilamino, trifluoromethoxybenzylamino, methoxycarbonylbenzylamino, ethoxycarbonylbenzylamino, phenylethylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonyl-amino, n-, i-, s- or t-butylsulfonylamino, N, N- (bismethylsulfonyl) amino, N, N- ( bis-ethylsulfonyl) -amino, N-methylsulfonyl-N-ethylsulfonyl-amino, N-methylsulfoni-1-N-propylsulfonylamino, N-acetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N-propionyl-N-methylsulfonyl-amino , N-propionyl-N-ethylsulphonyl-amino, Nn-butyroyl-N-methylsulphonyl-amino, N-butyroyl-N-ethylsulphonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-ethyl-sulfonyl-amino, Nn-valeroyl-N-methylsulfonyl-amino, Nn-valeroyl-N-ethyl-sulfonyl-amino, Ni-valeroyl-N-methylsulfonylamino, Ni-valeroyl-N-ethyl- sulfonyl-amino, Ns-valeroyl-N-methylsulfonyl-amino, Ns-valeroyl-N-ethylsulfonylamino, Nt-butyl-carbonyl-N-methylsulfonyl-amino, Nt-butyl-carbonyl-N-ethylsulfonyl-amino, N-benzoyl- N-methylsulfoni-amino, N-benzoyl-N-ethyl-sulfonyl-amino.

Group 2 In this case R2 has for example the meanings indicated above in group 1.

Group 3 In this case R 'has for example the meanings indicated above in group 1.

Group 4 In this case R2 has for example the meanings indicated above in group 1.

Team 5.

C 2H '"5 CF3 In this case R has for example the meanings indicated above in group 1.

Group 6 In this case R has for example the meanings indicated above in group 1.

Group 7 In this case R has for example the meanings indicated above in group 1 Group 8 In this case R has for example the meanings indicated above in group 1.

Group 9 In this case R2 has for example the meanings indicated above in group 1.

Group 10 In this case R2 has for example the meanings indicated above in group 1. If, for example, 3-amino-crotonate-methyl and 2,5-difluoro-4-trifluoromethyl-phenyl-isocyanate are used as starting material , the development of the reaction of the process according to the invention can be represented by means of the scheme of the following formulas: The esters of the aminoalkenoic acids to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R3 and R4 preferably have or especially those meanings which have already been indicated in a preferred manner or, more preferably, for R3 and R4 in connection with the description of the compounds of the formula (I) according to the invention. The starting materials of the formula (II) are known and / or can be prepared according to known processes (see J. Heterocycl, Chem. 9 (1972), 513-522). The p-trifluoromethylphenyl isocyanates to be further used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (III). In the formula (III), R1 and R2 preferably have or especially those meanings which have already been mentioned preferably or particularly preferably for R1 and R2 in connection with the description of the compounds of the formula (I) according to the invention . The starting materials of the formula (III) are known and / or can be prepared according to known processes (cf. EP 246061). The p-trifluoromethylphenyl isocyanates of the general formula (III) are obtained if p-trifluoromethylanilines of the general formula (V) are reacted wherein R1 and R2 have the meanings given above, with phosgene in the presence of a diluent, such as for example chlorobenzene, at temperatures between -20 ° C and +150 ° C (see for example also EP 648749). The p-trifluoromethylphenylurethanes, to be used as starting materials if appropriate in the process according to the invention, are generally defined by the formula (IV). In the formula (IV), R1 and R2 preferably have or especially those meanings which have already been mentioned preferably or, especially, preferred for R1 and R2 in relation to the description of the compounds of the formula (I) according to the invention; R preferably means alkyl having 1 to 4 carbon atoms, phenyl or benzyl, especially methyl or phenyl. The starting materials of the formula (IV) are not known by the literature; they are also an object of the present application as new products. The novel p-trifluoromethylphenylurethanes of the general formula (IV) are obtained if p-trifluoromethylanilines of the general formula (V) are reacted wherein R1 and R2 have the indicated meanings, with chlorocarbonyl compounds of the general formula (SAW) RO-CO-C1 (VI) wherein R has the above-indicated compound, optionally in the presence of an acid acceptor, such as, for example, pyridine, and, if appropriate, in the presence of a diluent, such as, for example, methylene chloride, at temperatures comprised between -20 ° C and + 100 ° C (see the preparation examples). Suitable reaction auxiliaries for the process according to the invention for the preparation of the compounds of the formula (I) are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals, such as, for example, sodium, potassium or calcium acetate, lithium amide, sodium, potassium or sodium amide. calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate, ethanolate, not i-propanolate, n-, i-, s- or sodium or potassium t-butanolate; also basic organic nitrogenous compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl -benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2, -dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3, 5-dimethyl-pi-ridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methylpiperidine, 1,4-diazabicyclo [2,2,2] -octane (DABCO), 1,5-diazabicyclo [4, 3, 0] -non-5-ene (DBN), or 1,8-diazabicyclo [5, 4, 0) -undec-7-ene (DBU).

Suitable diluents for carrying out the process according to the invention are, in particular, inert organic solvents. These include aliphatic, alicyclic, aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetraeloride; 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-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexainethyl-phosphorotriamide; esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethylsulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monooetiieter, their mixtures with water or water pure The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C. The process according to the invention is generally carried out at normal pressure. However, it is also possible to carry out the process according to the invention under higher pressure or at a lower pressure, generally between u, 1 bar and 10 bar. For carrying out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in the larger excess. The reaction is generally carried out in a suitable diluent in the presence of an auxiliary agent of the reaction and the reaction mixture is generally stirred for several hours at the required temperature. The processing is carried out according to the usual methods (see the preparation examples). The active compounds according to the invention can also be used as defoliants, desiccants, agents for removing broad-leaved plants and, especially, for destroying weeds. By weeds, plants that grow in places where they are unwanted are to be understood in the broadest sense. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: Bad dicotyledonous herbs of the following types: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Geleopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledonous crops of the classes: Cossypiu, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicum, Arachis, Brassica, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactuloctenium, Agrotis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

The use of the active compounds according to the invention is, however, not limited in any way to these classes, but extends in the same way also to other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. Likewise, compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, You can use the gum tree, palm oil, cocoa, berry and hops in ornamental and sporting paths and on surfaces for meadows and to selectively control weeds in mono-annual crops. The compounds of the formula (I) according to the invention are suitable for the control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous cultures both in the pre-emergence procedure and in the post-emergence process. The active ingredients can be converted into the customary formulations, such as solutions, emulsions, additives, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the product active, as well as microencapsulated in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid diluents, if appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly suitable liquid solvents are aromatic hydrocarbons, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane. or paraffins, for example, fractions of crude oil, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, solvents strongly polar, such as dimethylformamide and dimethyl sulfoxide as well as water. Suitable solid excipients are, for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid, aluminum and silicates, as solid excipients for granulates can be used broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, nut shells, coconut shells, corn husks and tobacco stalks; as emulsifiers and / or foam generators, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, as well as the products may be used. of albumin hydrolysis; suitable dispersants are, for example, sulphite residual liquors of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdery, granulated or latex-shaped, such as gum arabic, can be used in the formulations., polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue, and organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes and trace nutrients, such as sodium salts, can be employed. iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight. The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides for the control of weeds, with possible finished formulations or tank mixtures. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl). ), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop ( propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop-ethyl, Framprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsula, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoro glycofen (-ethyl), Flupoxam, Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr , Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenz-thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam , Metoxuron, Metsulfuron (-methyl), Metribuzin, Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pnedimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfide (-methyl), Prometryn , Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinch lorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbutbylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyri Tridiphane, Trifluralin and Triflusulfuron. It is also possible to mix with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, products that protect against ingestion by birds, nutrient products for plants and agents that improve the structure of the soil. The active products can be used as such, in the form of their formulations or in the forms of application prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. The application is carried out in a conventional manner, for example by watering, atomising, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated in the field before planting. The amount of active ingredient used can vary within wide limits. This depends, fundamentally, on the type of the desired effect. In general, the amounts applied are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per ha. The preparation and use of the active compounds according to the invention are illustrated by means of the following examples.

Preparation examples: Example 1.

A mixture consisting of 24.4 g (0.97 mol) of ethyl 3-amino-4, 4, 4-trifluoro-crotonate, 3.75 g of sodium hydride and 80 ml of N, N-dimethylformamide is stirred. approximately for 30 minutes at room temperature (approximately 25 ° C). After addition of 26 g (0, 97 mol) of N- (2, 5-difluoro-4-trifluoromethyl-phenyl) -O-ethyl-urethane, the reaction mixture is stirred for approximately 2 hours at 125 ° C to 130 ° C, after slight cooling. pour over ice water, acidify with hydrochloric acid and shake with ethyl acetate. The organic phase is separated, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with a mixture of 5 ml of ethyl acetate, 10 ml of diethyl ether and 300 ml of petroleum ether, and the precipitated crystalline product is isolated by filtration by suction. 19.1 g (55% of the theory) of 1- (2, 5-difluoro-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-2 (2H) are obtained. ) -pyrimidine with a melting point of 217 ° C.

Example 2, A mixture consisting of 1.8 g (5 mmol) of 1- (2, 5-difluoro-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6-dioxo-4 is heated to reflux for about 45 minutes. trifluoromethyl-1 (2H) -pyrimidine, 0.75 g (5 mmol) of dimethyl sulfate, 0.83 g of potassium carbonate and 30 ml of acetone and then evaporated under vacuum from the water tube. The residue is stirred with 50 ml of water / 50 ml of oil and the crystalline product is isolated by suction filtration. 1.4 g (75% of the theory) of 1- (2,5-difluoro-4-trifluoromethyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 are obtained. (2H) -pyrimidine with a melting point of 110 ° C.

Example 3, A mixture of 2.52 g (7 mmol) of 1- (2, 5-difluoro-4-trifluoromethyl-phenyl) -3,6-dihydro-2 is stirred for 8 days at room temperature (approximately 20 ° C). , 6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine, 1.6 g (7 mmol) of l-aminooxy-2,4-dinitro-benzene, 0.75 g of sodium bicarbonate and 20 ml of N , N-dimethylformamide. The mixture is then shaken with 5% sodium hydroxide / diethyl ether. The organic phase is washed with 5% sodium hydroxide solution and then with water, dried over sodium sulfate and filtered. The filtrate is concentrated by evaporation in a water pump vacuum, the residue is digested with 5 ml of diethyl ether / 10 ml of petroleum ether and the crystalline product is isolated by suction filtration. 0.95 g (36% of the theory) of 3-amino-1- (2,5-difluoro-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl are obtained. -l (2H) -pyrimidine with a melting point of 157 ° C.

Example A mixture of 10 g (27.8 mmol) of 1- (2, 5-difluoro-4-trifluophenyl-phenyl) -3,6-dihydro-2-6 is stirred for about 35 hours at 170 ° C. dioxo-4-trifluoromethyl-1 (2H) -pyrimidine, 5.8 g (27.8 mmol) of methanesulfonic acid amide, 12 g of potassium carbonate and 40 ml of N-methyl-pyrrolidone. After cooling to room temperature, pour the mixture over ice water. It is acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation in the vacuum of the water pump, the residue is digested with 0.5 ml of ethyl acetate / 3 ml of diethyl ether and the crystalline product is isolated by suction filtration. 3.6 g (30% of theory) (27.8 mmol) of 1- (2-fluoro-5-methylsulfonyl-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6-dioxo are obtained -4-trifluoromethyl-l (2H) -pyrimidine with a melting point of 227 ° C.

Example 5, A mixture of 1.0 g (2.3 mmol) of l- (2-fluoro-5-methylsulfonyl-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6 is heated at reflux for 7 hours. -dioxo-4-trifluoromethyl-l (2H) -pyrimidine, 0.31 g (23 mmol) of di-ethylsulfate, 0.21 g of sodium bicarbonate and 20 ml of acetone and then concentrated by vacuum evaporation of the tube of water. The residue is shaken with diethyl ether and 2N hydrochloric acid, the organic phase is separated, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation in a vacuum of the water pump, the residue is digested with diethyl ether and the crystalline product is isolated by suction filtration. 0.62 g (60% of theory) of 1- (2-fluoro-5-methylsulfonyl-4-trifluoromethyl-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4 are obtained. -trifluoromethyl-l (2H) -pyrimidine with a melting point of 163 ° C, analogously to the production examples 1 to 5, as well as according to the general description of the process for obtaining the invention can be prepared , for example, also the compounds of the formula (I) indicated in table 1 below.

Table i; Examples for obtaining dd products from the fdroula (I).

Starting products of the formula (IV) Example (IV-1). 11.7 g (104 mmol) of ethyl chloroformate are added, under stirring, to a mixture, cooled to 0 ° C, constituted by 20.5 g (104 mol) of 2,5-difluoro-4-trifluoromethyl-aniline, 8.5 g of pyridine and 200 ml of dichloromethane. The reaction mixture is stirred for 60 minutes at 0 ° C, then washed with 2N hydrochloric acid and with water, dried over sodium sulfate and filtered. The filtrate is concentrated by evaporation in a vacuum of the water pump, the residue is digested with petroleum ether and the crystalline product is isolated by suction filtration. 26.2 g (93.5% of the theory) of N- (2, 5-difluoro-4-trifluoromethyl-phenyl) -0-ethyl-urethane are obtained with a melting point of 92 ° C.

Application examples: Example A. Pre-emergence test. Solvent: 5 Parts by weight of acetone Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active substance, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil and after 24 hours are watered with the preparation of active product, so that the amount of active product desired per unit area is applied respectively. The concentration of the sprayable broths will be chosen in such a way that the quantities of active compound desired in each case are applied in 1000 1 of water / ha. After three weeks, the degree of damage of the plants compared with the development of the untreated control is evaluated in%. They mean: O% = no effect (same as untreated controls) 100% = total destruction. In this test, for example, the compounds according to Preparation Examples 2, 4 and 5 are shown, with a good partial compatibility with the crop plants, such as, for example, maize (0-10%), wheat (0). %), soybean (0%) and sugar beet (O%) a potent effect against weeds, such as Cyperus (80%), Sinapis (100%), Abutilon (80 - 100%), Chenopodium (80 - 100) %), Matricaria (90 - 100%) and Solanum (90 - 100% > Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active substance, 1 part by weight of the active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. With the active product preparation, test plants are sprayed, having a height of 5-15 cm, so that in each case the desired amounts of active substance per unit area are applied. The concentration of the sprayable broths is chosen so that the desired quantities of active compound in each case are applied in 1000 1 of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. They mean: I Q 0% = no effect (same as untreated controls) 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 2, 4 and 5, with a good partial compatibility with the plants of -, crop, such as, for example, corn (0), wheat (0 - 5%) and barley (0 - 10%) a potent effect against weeds, such as Sinapis (100%), Datura (100%) ), Ipomoea (100%), Polygonum (95%), Solanum (100%), Abutilon (100%) and Matricaria (100%). twenty It is noted that, in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, the content of the following is claimed as property: 15 20 25

Claims (9)

1. p-Trifluoromethylphenyluracils substituted of the general formula (I), characterized in that R 1 signifies hydrogen, cyano, or halogen, R 2 signifies the grouping A1-A2-A3, where A1 means a single bond, means O, S, -SO-, -S02-, -CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A1 further denotes alkanediyl, alkenodium, azaalkenodium, alkynediyl, cycloalkanediyl, cycloalkenodiyl or phenylene substituted, where appropriate, by halogen, A2 means a single bond, means 0, S, -SO-, -S02-, -CO- or the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A2 also means alkanediyl, alkenodiyl, azaalkenodiyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or substituted phenyl respectively, if appropriate by halogen, A3 means hydrogen, hydroxy, mercapto, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl substituted, where appropriate, by halogen or alkoxy, means alkenyl, alkenyloxy, alkenylamino, alkylidene, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkylamino or alkynyloxycarbonyl respectively substituted, if appropriate, by halogen, means cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloa polyalkoxycarbonyl or cycloalkylalkoxycarbonyl respectively substituted, where appropriate, by halogen, cyano, carboxy, alkyl and / or alkoxycarbonyl, or means aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl respectively substituted by nitro, by cyano by carboxy, by halogen, by alkyl, by haloalkyl, by alkoxy, by haloalkoxy and / or by alkoxycarbonyl, A3 also means pyrrolyl, piperazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl , thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, triazinyl, pyrazolylalkyl, furyalkyl, thienylalkyl, oxazolylalkyl, isoxazoalkyl, thiazoalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy hydrogenated, if appropriate wholly or partly, means perhydropyranylalkoxy or pyridylalkoxy, R3 means hydrogen, halogen or alkyl optionally substituted by halogen, R 4 means alkyl substituted, if appropriate, by halogen, and R 5 is hydrogen, amino or alkyl optionally substituted by hydroxy, cyano, halogen or alkoxy.

2. Substituted p-Trifluoromethylphenyluracils of the general formula (I) according to claim 1, characterized in that R 1 is hydrogen, cyano, fluorine, chlorine or bromine, R 2 is the group A1-A2-A3, where A1 is a single bond, means 0, S, -SO-, -S02-, -CO- or the grouping -N-A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl , alkylsulfonyl with 1 to 4 carbon atoms or phenyl sulfonyl, A1 further means alkanediyl with 1 to 6 carbon atoms alkenodiyl with 2 to 6 carbon atoms, alkenodiyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms , cycloalkenediyl having 3 to 6 carbon atoms or phenylene substituted, where appropriate, by fluorine or chlorine, A2 means a single bond, means 0, S, -SO-, -S02-, -CO- or means grouping -N -A4-, where A4 means hydrogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, phenyl, alkylsulfonyl with 1 to 4 carbon atoms or phenylsulfonyl, A2 also means alkanediyl with 1 to 6 carbon atoms, alkenodiyl with 2 to 6 carbon atoms, alkynediyl with 2 to 6 carbon atoms, cycloalkanediyl with 3 to 6 carbon atoms, cycloalkenodiyl with 3 to 6 carbon atoms or phenylene substituted, where appropriate, by fluorine or chlorine, respectively hydrogen, hydroxy, mercapto, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl with respectively 1 to 6 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms, means alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl , alkynyloxy, alkynylamino or alkynyloxycarbonyl with 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, substituted respectively, where appropriate fluorine, chlorine or bromine, means cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl with 3 to 6 carbon atoms in the cycloalkyl groups, and optionally 1 to 4 carbon atoms in the alkyl groups substituted respectively by fluorine, by chlorine, by bromine, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or by alkoxy-carbonyl with 1 to 4 carbon atoms, or phenyl, phenyloxy, phenyl-C 1 -C 4 -alkyl, phenylalkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or phenylalkoxycarbonyl with 1 to 4 carbon atoms, optionally substituted respectively by nitro, by cyano, by carboxy, by fluorine , by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by h halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalco xi with 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms, means (Respectively hydrogenated optionally wholly or partially) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1 4 carbon atoms, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl-alkyl with 1 to 4 carbon atoms, isoxazole-alkyl with 1 to 4 carbon atoms, thiazole alkyl having 1 to 4 carbon atoms pyridinyl-C1-C4-alkyl, pyrimidinyl-alkyl having 1 to 4 carbon atoms, pirazolilmetoxi, furylmethoxy, means perhidropiranilmetoxi or pyridylmethoxy, R3 represents hydrogen, fluorine, chlorine, bromine or alkyl having from 1 to 4 carbon atoms optionally substituted by fluorine and / or by chlorine, R4 means alkyl having 1 to 4 carbon atoms, optionally substituted by fluorine and / or chlorine, and R5 is hydrogen, amino or alkali; uilo with 1 to 4 carbon atoms, optionally substituted by hydroxy, by cyano, by fluorine, by chlorine, or by alkoxy with 1 to 4 carbon.

3. Substituted p-trifluoromethylphenyluracils of the general formula (I) according to claim 1, characterized in that R 1 is hydrogen, fluorine or chlorine, R 2 is the group A1-A-A3, where A1 is a single bond, means O, S, -SW-, -S02-, CO- or means the group -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, A1 also means methylene, ethane-1, l-diyl, ethane-1,2-diyl, propane-1, l-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2- diyl, propene-1, 2-diyl, propene-1,3-diyl, etino-1,2-diyl or propino-1,3-diyl, A2 means a single bond, means O, S, -SO-, S02-, -CO- or means the grouping -N-A4-, where A4 means hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n - or 1-propylsulfonyl or phenylsulfonyl, A2 further means methylene, ethane-1, 1-diyl, ethane-1,2-diyl, propane-1, 1-diyl, propane-1,2-diyl, propane-1, 3-diyl, ethene-1,2-diyl, propene-1, 2-diyl, propene-1,3-diyl, etino-1,2-diyl or propino-1,3-diyl, A3 means hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluoro, chloro, bromo, means methyl, ethyl, n- or 1-propyl, n-, i-, s- or t-butyl, n-, i-, s - or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- i-propylthio, n-, i-, s- or t- butylthio, methylsulfinyl, ethylsulfinyl, n- or 1-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or 1-propylsulfonyl, methylamino, ethylamino, n- or i- propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxy rbonyl ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, means propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino , propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, optionally substituted, if appropriate, by fluorine or chlorine, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, ciciohexilmetilo, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, ciclohexilidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, ciclopentilmetoxicarbonilo substituted or res ciclohexilmetoxicarbonilo spectively optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, or represents phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl substituted in each case optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, eti it, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n - or i- propoxy, by difluoromethoxy, by trifluoromethoxy, by methoxycarbonyl and / or by ethoxycarbonyl, means (optionally hydrogenated, in whole or in part) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolylmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R3 denotes hydrogen, fluorine, chlorine, bromine or means methyl or ethyl substituted respectively by fluorine and / or chlorine, R4 is methyl or ethyl substituted respectively by fluorine and / or chlorine, and R5 is hydrogen, amino or methyl or ethyl substituted respectively by hydroxy, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy.

4. Process for obtaining the substituted p-trifluoromethylphenyluracils of the general formula (I) wherein R1, R2, R3, R4 and R5 have the meanings indicated in claim 1, characterized in that esters of aminoalkenoic acids of the general formula (II) are reacted wherein R3 and R4 have the meanings indicated above and R means alkyl, aryl or arylalkyl, with p-trifluoromethylphenyl isocyanates of the general formula (III) wherein R1 and R2 have the meanings indicated above, or with p-trifluoromethylphenylurethanes (p-trifluoromethylphenylcarbamates) of the general formula (IV) wherein R, R1 and R2 have the meanings indicated above.

5. Herbicidal agents, characterized in that they have a content in at least one p-trifluoromethylphenyluracil of the formula (I) according to claim 1.

6. Process for the control of undesirable plants, characterized in that p-trifluoromethylphenyluracils of the formula (I) according to claim 1 are allowed to act on the undesirable plants and / or on their environment.

7. Use of the p-trifluoromethylphenyluracils of the formula (I), according to claim 1, for the control of undesirable plants.

8. Process for the preparation of herbicidal agents, characterized in that the p-trifluoromethylphenyluracils of the formula (I) are mixed according to claim 1, with excipients and / or surfactants.

9. p-trifluor ethylphenylcarbates of the general formula (IV) characterized in that R1 and R2 have the meanings indicated above, in claim 1 v R represents alauyl, aru or a r i such chyl.