MXPA99005614A - Heterocyclyl uracils - Google Patents

Abstract

The invention relates to novel heterocyclyl uracils of formula (I) wherein R1, R2 and Het have the meanings cited in the description, as well as to a method for the production of these substances and the use thereof as herbicides.

Description

HETEROCIC ILURACILOS. Field of the invention. The present invention relates to new heterocyclyluracils, a process for their preparation and their use as herbicides. Description of the prior art. A large number of heterocyclyluracils with herbicidal or insecticidal properties have already been disclosed (see JP-A 91-287 585, JP-A 93 202 031, Chem. Abstr 116, 235650 and Chem. Abstr 120). , 107,048). Thus, for example, 1- (3-chloro-5-trifluoromethylpyridin-2-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine can be used for the fight against weeds. However, with low application quantities, the activity of this product is not always satisfactory. Detailed description of the invention. New heterocyclyluracils of the formula have now been found wherein R 1 means formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, thiocarbamoyl or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, R 2 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen and Het means pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, these radicals being optionally substituted one to three times, in the same or in different forms by hydroxy, mercapto, amino, cyano, nitro, carboxy , carbamoyl, thiocarbamoyl, halogen, alkyl with 1 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms bond and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, halogenoalkylsulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkylsulphinyl with 1 to 6 carbon atoms and 1 to 5 atoms of halogen, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, halogenoalkylcarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, haloalkoxy- carbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, halogenoalkylamino with 1 to 5 carbon atoms of halogen and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, halogenoalkylsulfonylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part, N, N-bis-alkylsulfonylamino with 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonium l-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part N-halogen-alkyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, n-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms carbon in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulphonyl part and / or N-alkylsulphonyl-N-phenylcarbonyl amino with 1 to 6 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different manner by halogen, by alkyl having 1 to 4 carbon atoms, by dialkylamino having 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms. It has also been found that the heterocyclyluracils of the formula (I) are obtained, if a) in a first step, aminoalkenoic acid esters of the formula are reacted in which R1 and R2 have the meanings indicated above and R means alkyl, aryl or arylalkyl, or a) with heterocyclylisocyanates of the formula 0 = C = N-Het (III), in which Het has the meaning indicated above, or ß) with heterocyclic carbamates of the formula H, 3 and Het W) 'O wherein Het has the meaning indicated above and R 3 signifies alkyl, aryl, or arylalkyl, respectively, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, and b) in a second step they are made react the heterocyclyluracils obtained from the formula H RVN? OR Y ° (V),. AND R2? N HHeett O wherein R1, R2 and Het have the meanings indicated above, with l-aminooxy-2,4-dinitrobenzene of the formula if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent. Finally, it has been found that the new heterocyclyluracils of the formula (I) have very good herbicidal properties. Surprisingly, the heterocyclyl uracils according to the invention of the formula (I) have a substantially better herbicidal activity than the previously known active compounds, which are similar from the point of view of their constitution, with the same activity direction. HE. they will mean alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, haloalkoxy and haloalkylthio, in the present case, respectively straight-chain or branched chain residues. In the present case, halogen means, when not otherwise stated, fluorine, chlorine, bromine or iodine. The heterosycliluracils according to the invention are so defined in general by means of formula (I). Prence is given to compounds of the formula (I), in which R.sub.1 is formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy, carbamoyl, thiocarbamoyl group or means alkyl having 1 to 3 carbon atoms optionally substituted one to three times, likewise or difntly by fluorine and / or by chlorine, R 2 means hydrogen, cyano, fluorine, chlorine, bromine or means alkyl having from 1 to 3 carbon atoms, optionally substituted one to three times, in the same or difnt forms by fluorine and / or chlorine and Het means pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, these radicals being optionally substituted. one to three times, in the same or in difnt ways by hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 to 4 atoms of carbon in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, halogenoalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkoxyalkoxy with 1 to 4 atoms of carbon in each part alsoxi, alkylthio with 1 to 4 carbon atoms, halogenalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, halogenalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 halogen atoms and 1 to 4 carbon atoms or, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 atoms of carbon in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl- amino with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the part alkylsulfonyl, N-halogeno-quil-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfo-nil-amino with 1 to 4 carbon atoms carbon in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the haloalkyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the couple halogenalkylsulfonyl and / or N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different ways by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamino, by methoxy, by ethoxy, by n-propoxy and / or by i-propoxy. Particularly preferred are the heterocyclyluracils of the formula (I), in which R 1 is carboxy, methoxycarbonyl, cyano, carbamoyl, thiocarbonyl or means methyl or ethyl substituted one to three times, in the same or in different forms by fluorine and / or per chlorine, R2 means hydrogen, fluorine, chlorine, bromine or methyl and Het means pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, these radicals being optionally substituted one to three times, same or differently by hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 or 2 carbon atoms in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, halogenoalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 or 2 carbon atoms, alkoxyalkoxy with 1 or 2 carbon atoms e Each part is alkoxy, alkylthio having 1 or 2 carbon atoms, haloalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms, halogen- alkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms , alkylcarbonyl with 4 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part , halogen-alkoxycarbonyl having 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino having 1 to 3 carbon atoms, dialkylamino having 1 to 3 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 fluoro and / or chloro atoms and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, hal genoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino not with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkylsulfonyl part, N-haloalkyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N-haloalkylcarbonyl-N -halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atoms of carbon in the halogenoalkylsulphonyl part and / or N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part optionally substituted one to three times, in the same or in different ways by fluorine , by chlorine, by bromine, by methyl, by ethyl, by dimethylamino, by diethyl lamino, by methoxy and / or by ethoxy. Very particular preference is given to heterocyclyluracils of the formula (I), in which R 1 is carboxy, methoxycarbonyl, cyano, carbamoyl, thiocarbamoyl, methyl or trifluoromethyl, R2 means hydrogen and Het means one of the heterocyclic radicals of the following formulas: The definitions of the residues indicated above are valid both for the final products of the formula (I) and correspondingly for the starting materials or the intermediate products necessary respectively for the preparation. The definitions of the remains can be combined arbitrarily with each other, that is to say even between the indicated intervals. If the methyl 3-amino-crotonate and the pyridin-3-yl-isocyanate are used as starting materials, and the l- (pyridin-3-yl) -3,6-dihydro-2,6- is reacted dioxo-4-methyl-l (2H) -pyrimidine, obtained in this case, with l-aminooxy-2,4-dinitro-benzene, the development of the process according to the invention can be represented by means of the following formula scheme: If ethyl 3-amino-4,4,4-trifluorocrotonate and N- (2-chloro-3-cyano-4-methyl-pyridin-6-yl) -carbamate are used as starting compounds and reacted Ial- (2-chloro-3-cyano-4-methyl-pyridin-6-yl) -3,6-dihydro- 2, 6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine, obtained in this case, with l-aminooxy-2,4-dinitro-benzene, the development of the process according to the invention can be represented by the formula scheme following: The esters of the aminoalkenoic acids which are necessary as starting materials in carrying out the first step of the process according to the invention are generally defined by the formula (II). In the formula (II), R1 and R2 preferably have or especially those meanings that have already been mentioned above, preferably or in a manner especially preferred for R1 and R2 in relation to the description of the compounds of the formula (I) according to the invention. In this case, R is preferably alkyl having 1 to 4 carbon atoms, phenyl or benzyl, particularly preferably methyl, ethyl, phenyl or benzyl. The esters of the aminoalkenoic acids of the formula (II) are known or can be prepared by processes known per se (see J. Heterocycl Chem. 9 (1972), 513-522). The heterocyclylisocyanates required as components of the reaction in the embodiment of variant a in the first step of the process according to the invention are generally defined by means of formula (III). In the formula (III), Het preferably has or especially those meanings which have already been mentioned above in a preferred manner or, more preferably, in Het in relation to the description of the compounds of the formula (I) according to the invention. The heterocyclylisocyanates of the formula (III) are known or can be prepared by processes known in principle (cf. EP-A-0555 770 and EP-A 0 600 836). In this way, the hetero-cyclisocyanates of the formula (III) can be prepared, if they are made reacting heterocyclylamines of the formula H2N-Het (VII) in which Het has the meaning indicated above, with phosgene in the presence of a diluent, such as for example chlorobenzene, at temperatures between -20 ° C and + 150 ° C. The heterocyclylamines of the formula (VII) are known or can be prepared by processes known per se. The heterocyclylcarbamates required as components of the reaction in the embodiment according to the β-variant in the first step of the process according to the invention are generally defined by means of formula (IV), Het preferably having or especially those meanings which have already previously mentioned in a preferred manner or, more preferably, in Het in relation to the description of the compounds of the formula (I) according to the invention. Preferably R3 means alkyl having 1 to 4 carbon atoms, phenyl or benzyl, especially means methyl, ethyl or phenyl. The heterocyclylcarbamates of the formula (IV) are known or can be prepared by processes known in principle (cf. EP-A 0555 770 and EP-A O 600836). In this way, the heterocyclylcarbamates of the formula (IV) are obtained if heterocyclylamines of the formula H 2 N-Het (VII) are reacted, wherein Het has the meaning indicated above, with chlorocarbonyl compounds of the formula R 30 -C0- C1 (VIII), in which R3 has the meaning indicated above, optionally in the presence of an acid acceptor, such as, for example, pyridine, and optionally in the presence of a diluent, such as, for example, methylene chloride, at temperatures between -20 ° C and + 100 ° C. The heterocyclyl uracils required as starting materials in carrying out the second step of the process according to the invention are generally defined by the formula (V). In this case, these are products that can be prepared according to the first stage of the process according to the invention. The l-aminooxy-2,4-dinitro-benzene necessary as a component of the reaction in the embodiment of the second stage of the process according to the invention, of the formula (VI), is also known (cf. EP-A 0476 697) .

As acid acceptors in carrying out the first step of the process according to the invention, both the usual inorganic and organic bases are suitable according to variant (a) and also according to the variant (ß). Preference is given to using acetates, amines, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals, such as sodium, potassium or calcium acetate, lithium amide, sodium, potassium or calcium amines. , 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 trimethylamine, triethylamine, tripro-phenylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethylbenzylamine, pyridine, 2-methyl-, 3-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, 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 in carrying out the first step of the process according to the invention according to variants (a) or (ß) are all customary inert organic solvents and also water. Aliphatic, alicyclic or aromatic hydrocarbons, optionally halogenated, may be used, 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, pro-pionitrile or butyronitrile; amides, such as N, N-dimethyl-formamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; or sulfoxides, such as dimethylsulfoxide. The reaction temperatures in carrying out the first step of the process according to the invention can vary within wide limits. Both in the embodiment of the variant (a) and also of the variant (ß), the working is generally between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C. In carrying out the first stage of the pro- According to the invention, according to the variants (a) and (ß), the process is generally carried out under atmospheric pressure. However, it is also possible to work under higher pressure or at a lower pressure, for example between 0.1 and 10 bar. In carrying out the first step of the process according to the invention, in the case of variant (a), an approximately equimolar amount of heterocyclylisocyanate of the formula is used per 1 mole of the aminoalkenoic acid ester of the formula (II) III) and, in the case of the variant (ß), an approximately equimolar amount of heterocyclic carbamate of the formula (IV). However, it is also possible to use one of the components in a larger excess respectively. The reactions are carried out, in general, in a suitable diluent and in the presence of an acid-accepting agent. In this case, the process is carried out in such a way that the reaction mixture is stirred at the required temperature for as long as necessary and then processed according to usual methods. As acid-binding agents, all the usual inorganic and organic bases are suitable for carrying out the second step of the process according to the invention. Preferably, those acid acceptors which have already been mentioned can be used in relation to the description of the first step of the method according to the invention. Suitable diluents in the embodiment of the second stage of the process according to the invention are all the usual inert organic solvents for this type of reaction. Preference is given to using nitriles, such as acetonitrile and bu-tironitrile, ketones, such as acetone and furthermore amides, such as dimethylformamide and N-methylpyrrolidone. The reaction temperatures in the embodiment of the second stage of the process according to the invention can also vary within wide limits. In general, work is carried out at temperatures between 0 ° C and 80 ° C, preferably between 10 ° C and 60 ° C. Also in the embodiment of the second stage of the process according to the invention, work is generally carried out under atmospheric pressure. However, it is also possible to work under higher pressure or at a lower pressure as long as no volatile components participate in the reaction. In the embodiment of the second step of the process according to the invention, an approximately equimolar amount of l-aminooxy-2,4-di-nitrobenzene of the formula is used per 1 mole of the heterocyclyluracil of the formula (V). SAW) . However it is possible also use one of the components in a larger excess. Working up is carried out by customary methods. The active compounds according to the invention can be used as defoliants, desiccants, agents for removing harmful plants, especially for destroying weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. 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: Dicotyledonous bad herbs of the kinds: Sinapis, Le-pidium, Galium, Stellaria, Matricaria, Anthemis, Galinso-ga, Chenopodium, Urtica, Senecio, Amaranthus , Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Ro-tala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium , Ra-nunculus, Taraxacu. Dicotyledonous crops of the following classes: Gossypium, Gly-cine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brass Sica, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the following kinds: Echino-chloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Brous, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Oats, 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. Also, 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, tea , of the rubber tree, of oil palms, of cocoa, of berries and hops, on ornamental and sports paths and in 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 cultures both in the pre-emergence procedure and in the post-emergence process. They also show good compatibility with the most important crop plants, such as corn and wheat The active products can be transformed into the usual formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural materials and synthetic impregnated with the active product, as well as micro-encapsulated in polymeric 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 / or foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. As I say liquid solvents are especially suitable: 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, the solvents strongly polar, such as dimethylformamide and dimethylsulfoxide 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 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, can be used. husks of coconut, ears of corn and tobacco stalks; as emulsifiers and / or foam generators, the non-ionogenic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, poly-oxyethylenated fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, can be used. the products of albumin hydrolysis; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or in the form of latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and phospholipids, can be used. synthetic 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 salts of 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 for the 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, Carbetami-de, Chlomethoxyfen, Chloramben, Chloridazon, Chlori u-ron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransu-lam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfa-muron, Cycloxydim, Cyhalofop (-butyl), 2,4 -D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Di-methachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr , Diuron, Dymron, EPTC, Es-procarb, Ethalfluralin, Etham etsulfuron (-methyl), Ethofu- wet, Ethoxyfen, Etobenzanid, Fenoxaprop- (ethyl), Framprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluome-turon, Fluorochloridone, Fluoroglycofen (-ethyl) , Flupoxam, Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimi-dol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl) -Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imaza -mox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflute-le, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobro uron, Metolachlor, Metosulam, Meto-xuron, Metsulfuron (-methyl), Metribuzin, Molinate, Monoli-nuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Preti-lachlor, Primisulfuron (-meti) l), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Pro-sulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarbazil, Tral oxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, 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, new 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. It depends, fundamentally of 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. Examples of obtaining. Example 1 a) First stage A mixture consisting of 14.9 g (50 mmol) of ethyl 3-amino-4,4,4-trifluoro-crotonate, 13,8 g of potassium carbonate and 100 ml of N-methyl-pyrro-lidone is stirred. for 1 hour under nitrogen at 100 ° C. Then 10.0 g (50 mmol) of N- (2-chloro-pyridin-5-yl) -O-ethyl-carbamate are added and the reaction mixture is heated at about 130 ° C for 4 hours in the HE- water hostel. Allow to cool under nitrogen to room temperature, then pour into 1 liter of water and extract three times with 100 ml of methylene chloride each time. After acidification with concentrated hydrochloric acid (up to pH 3), it is left to stand for 1 hour and the crystalline product is isolated by suction filtration. 10.6 g (75% of theory) of l- (2-chloro-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l- (2H) are obtained. ) -pyrimidine with a melting point of 158 ° C. b) Second stage. 3 g (13 mmol) of l-aminooxy-2,4-di-nitro-benzene are added, at room temperature, over the course of 60 minutes, in portions, with stirring, to a mixture consisting of 2.9 g ( 10 mmoles) of l- (2-chloro-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine, 0.9 g of sodium bicarbonate and 50 ml of N, N-dimethyl-formamide. The reaction mixture is stirred for 48 hours at room temperature. Then it is poured over a saturated aqueous solution of Sodium chloride and extracted several times with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and filtered through silica gel. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with ethyl acetate and the crystalline product is isolated by suction filtration. 1.7 g (55% of theory) of 3-ami-no-1- (2-chloro-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4-tri- Fluomethyl-l- (2H) -pyrimidine with a melting point of 235 ° C. Obtaining the starting substance of the formula: 11 g (0.1 mol) of ethyl chloroformate are added dropwise, with stirring, to a mixture of 12.8 g (0.1 mol) of 2-chloro-5-amino-pyridine. , 8 g of pyridine and 200 ml of methylene chloride and the reaction mixture is stirred for 3 hours at room temperature. It is then washed with 1N hydrochloric acid, dried over sodium sulfate and filtered through silica gel. The solvent is carefully removed by distillation of the filtrate under vacuum from the tube of water. 18.6 g (93% of theory) of N- (2-chloro-pyridin-5-yl) -0-ethyl-carbamate are obtained as a crystalline product with a melting point of 110 ° C. According to the methods given above, the compounds of the formula (I) indicated in the following examples are also prepared. Example 2 P.f. = 223 ° C. Example 3 P.f. > 216 ° C.

Example 4 P.f. > 193 ° C. Example 5 P.f. 190 ° C. Example 6 P.f. 270 ° 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 compound, 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: 0% = no effect (same as untreated controls) 100% = total destruction. In this test the compounds according to the preparation examples 1 and 2 are shown, with a partially good compatibility with the crop plants, such like corn and soy, a powerful effect against weeds. 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 compound, 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 preparation of active product, test plants are sprayed, having a height of 5 - 15 cm, so that in each case, the desired quantities of active product per unit area are applied. The concentration of the sprayable broths is selected in such a way that the desired quantities of active product are applied in each case 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: 0% = no effect (same as untreated controls) 100% = total destruction.

In this test, the compounds according to Preparation Examples 1 and 2 show a partially good compatibility with crop plants, such as wheat, a potent effect against weeds. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (5)

1. CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. - Heterocyclyluracils of the formula characterized because; R1 means formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, thiocarbamoyl or means alkyl having 1 to 4 carbon atoms, optioy substituted by halogen, R2 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms substituted in each case by halogen and Het means pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrazolyl, oxazolyl, isoxazolyl or thiazolyl, these radicals being optioy substituted one to three times, in the same or in different forms by hydroxy, mercapto, amino, cyano, nitro, carboxy , carbamoyl, thiocarbamoyl, halogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms , halogeoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, al-coxialkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogeylthio with 1 to 6 carbon atoms and 1 to 5 atoms of halogen, alkylsulfinyl with 1 to 6 carbon atoms, halogenoalkylsulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 atoms of halogen, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, halogenoalkoxy -carbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, halogenoalkylamino with 1 to 5 atoms of halogen and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylatedocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, haloalkyl sulfonylamino with 1 to 5 halogen atoms and 6 carbon atoms in the halogenoalkyl part, N, N-bis-alkylsulfonylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino having 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the part alkylsulfonyl N-halogeno-alkyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, n-alkylcarbonyl-N-alkylsulfonyl-amino with the 6 carbon atoms in the alkyl part of the group alkylcarbonyl and 1 to 6 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part sulfonyl and / or N-alkylsul-fonyl-N-phenylcarbonyl-amino having 1 to 6 carbon atoms in the alkylsulfonyl part, optioy substituted one to three times, in the same or different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms.
2. 2. Process for obtaining heterocyclyluracils of the formula (I) according to claim 1, characterized in that a) in a first step, aminoalkenoic acid esters of the formula are reacted wherein R1 and R2 have the meanings indicated above And R means alkyl, aryl or arylalkyl, or a) with heterocyclylisocyanates of the formula 0 = C = N-Het (III), in which Het has the meaning indicated above, ß) with heterocyclic carbamates of the formula in which Het has the meaning indicated above and R3 means alkyl, aryl, or arylalkyl, respectively, if appropriate in the presence of. an acid-accepting agent and, if appropriate, in the presence of a diluent, and b) in a second step the heterocyclyluracils obtained from the formula are reacted wherein R1, R2 and Het have the meanings given above, with l-aminooxy-2,4-dinitrobenzene of the formula if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent.
3. 3. Herbicidal agents, characterized in that they have a content in at least one heterocyclyluracil of the formula (I) according to claim 1.
4. 4. Use of the heterocyclyluracils of the formula (I) according to claim 1, for the control tra the weeds.
5. 5. - Method for the fight against weeds, characterized in that the heterocyclyluracils of the formula (I) according to claim 1 are applied on the weeds and / or on their environment. 6. - Process for obtaining herbicidal agents, characterized in that heterocyclyluracils of the formula (I) are mixed according to claim 1, with spreaders and / or surfactant products.