MXPA99006934A - Substituted phenyltriazolin(thi)ones and their use as herbicides - Google Patents

Abstract

The invention concerns novel substituted phenyltriazolin(thi)ones of general formula (I) in which Q1 and Q2 are identical or different and stand for O or S, R1 stands for hydrogen, cyano, halogen or for one of the groups -R6, -O-R6, -SR6, -SO-R6 or -SO2-R6, R2 stands for hydrogen, hydroxy, amino or for one of the groups -R6, -O-R6 or -N=CR6R7, R3 stands for hydrogen, halogen, alkyl or alkyl halide, R4 stands for hydrogen, alkoxycarbonyl or for one of the groups -R6, -O-R6, -SR6, -NH-R6 or -NR6R7, R5 stands for amino, hydroxy or for one of the groups -R6 or -NR6R7, R6 stands for an in each case optionally substituted group selected from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl, aryloxyalkyl, arylalkoxyalkyl, heterocyclyl or heterocyclyalkyl, and R7 stands for hydrogen or for an in each case optionally substituted group selected from the series comprising alkyl, alkenyl, alkinyl or cycloalkyl. The invention also concerns a process for their preparation and their use as herbicides.

Description

FENILTRIAZOLIN (TIO) ONAS SUBSTITUIDAS AND Sü EMPLOYMENT AS HERBICIDES. Field of the invention. The invention relates to novel substituted phenyltriazolin- (thio) -ones, processes for their preparation and their use as herbicides. Description of the prior art. It has already been disclosed that certain substituted phenyl triazolin (thio) atoms exhibit herbicidal properties (see EP 609734 / US 5464810). The substituted phenyltriazolin (thio) atoms known up to the present, however, have not acquired any special significance. Detailed description of the invention. New substituted phenyltriazolin- (thio) ones of the general formula (I) have now been found, wherein Q1 and Q2 are the same or different and mean O or S, R1 signifies hydrogen, cyano, halogen, or means one of the radicals -R6, -O-R6, -SR6, -SO-R6 or -S02-R6 , R 2 signifies hydrogen, hydroxy, amino, or means one of the radicals -R 6, -O-R 6 or -N = CR 6 R 7, R 3 signifies hydrogen, halogen, alkyl or haloalkyl, R 4 signifies hydrogen, means alkoxycarbonyl, or means one of the residues -R6, -O-R6, -SR6, -NH-R6 or -NR6R7, R5 means amino, hydroxy or means one of the remains -R6 or -NR6R7, R6 means a radical, respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, aryloxyalkyl, arylalkoxyalkyl, heterocycle or heterocyclylalkyl, and R7 is hydrogen or represents a radical , respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl or cycloalkyl. It has also been found that the new substituted triazolin (thio) ons of the general formula (I) are obtained, if phenyltriazolin (thio) ons of the general formula (II) are reacted. wherein Q1, R1, R2, R3 and R5 have the meanings given above, with halogen (thio) carbonyl-compounds of the general formula (III) wherein Q2 and R4 have the meanings indicated above, and X means halogen, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. It has also been found that the new substituted phenyltriazolin (thio) ons of the general formula (I) are characterized by a strong and selective herbicidal activity. The substituted phenyltriazolin (thio) ons according to the invention are generally defined by the formula (I). Preferred are the compounds of the formula (I), in which Q1 and Q2 are the same or different and mean 0 or S, R1 is hydrogen, cyano, fluorine, chlorine, bromine, iodine, or represents one of the radicals -R6, -O-R6, -S-R6, -SO-R6 or -S02-R6, R2 means hydrogen, hydroxy, amino or means one of the radicals -R6, -0-R6 or -N = CR6R7, R3 means hydrogen, fluorine, chlorine, bromine, iodine, means straight chain or branched chain alkyl with 1 to 4 carbon atoms or means straight chain or branched chain halogen with 1 to 4 carbon atoms and 3 equal or different halogen atoms - especially fluorine, chlorine or bromine, R4 means hydrogen, means alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy group, or means one of the radicals -R6, -O-R6, -S-R6, -NH-R6 or -NR6R7, R5 means amino, hydroxy or means one of the remains -R6 or -NR6R7, R6 means straight-chain or branched-chain alkyl, optionally substituted one or more times, in the same or in different forms, with 1 to 10 carbon atoms, with substituents being preferred: halogen -especially fluorine, chlorine and / or bromo-, cyano, carboxy, carbamoyl, thiocarbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N, N-dialkylaminocarbonyl , trialkylsilyl or alkylsulfonylaminocarbonyl, respectively straight-chain or branched chain, with respectively 1 to 6 carbon atoms in the individual alkyl or heterocyclyl groups, the heterocyclyl radical meaning a heterocycle with 5 to 7 members, given benzoanillado, saturated or unsaturated, with 1 to 3 identical or different heteroatoms -especially nitrogen, oxygen and / or sulfur-; R6 also means alkenyl or alkynyl, with 2 to 8 carbon atoms each, optionally substituted one or more times, in the same or different manner by halogen, especially fluorine, chlorine and / or bromine; R6 further denotes cycloalkyl with 3 to 7 carbon atoms, optionally substituted one or more times, in the same or different manner by halogen, especially fluorine, chlorine and / or bromine, and / or by straight-chain alkyl or branched chain with 1 to 4 carbon atoms; R6 also means aryl, arylalkyl, aryloxyalkyl or arylalkoxyalkyl, each optionally substituted in the aryl part one or more times, in the same or in different ways, with 6 to 10 carbon atoms respectively in the aryl part and, if appropriate, 1 to 4 carbon atoms in the straight-chain or branched-chain alkyl part, or means a heterocyclyl radical optionally substituted one or more times, in the same or different forms and / or benzo-ring, saturated or unsaturated, with 5 to 7 members, with 1 to 3 identical or different heteroatoms, especially hydrogen, oxygen and / or sulfur - preferred as substituents of aryl or heterocyclyl: halogen, cyano, nitro, amino, N-acetylamino, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, respectively straight-chain or branched chain, with 1 to 6 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl or halogenoalkylsulfonyl, respectively straight-chain or branched chain, with respectively 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, respectively alkoxycarbonyl or alkoxyiminoalkyl, straight-chain or branched chain with respectively 6-carbon atoms carbon in the individual alkyl groups and also phenyl, optionally substituted one or more times, in the same or different manner by halogen and / or by straight-chain or branched-chain alkyl or alkoxy with 1 to 6 carbon atoms and / or by straight chain or branched chain haloalkyl or halogenoalkoxy with 1 to 6 carbon atoms and 1 to 3 same or different halogen atoms; R7 means hydrogen or means straight-chain alkyl 0 of branched chain, replaced if necessary one or several times, in the same or in different ways, with 1 to 8 carbon atoms, by substituting: halogen, especially fluorine, chlorine and / or bromine, cyano, carboxy, carbamoyl, thiocarbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-alkyl aminocarbonyl, N, N-dialkyl-aminocarbonyl, trialkylsilyl or alkylsulfonylaminocarbonyl respectively straight-chain or branched chain with 1 to 8 carbon atoms in the individual alkyl or heterocyclyl groups, the heterocyclyl radical meaning a heterocycle with 5 to 7-membered, optionally benzo-napped, saturated or unsaturated, with 1 to 3 identical or different heteroatoms, -especially nitrogen, oxygen and / or sulfur-; R7 further denotes alkenyl or alkynyl. with respectively 2 to 8 carbon atoms, each optionally substituted one or more times, in the same or in different ways by halogen-especially fluorine, chlorine and / or bromine; R7 further denotes cycloalkyl having 3 to 7 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen - especially fluorine, chlorine and / or bromine - and / or straight-chain alkyl or branched chain with 1 to 4 carbon atoms. Especially preferred are the compounds of the formula (I), in which Q1 and Q2 are the same or different and mean 0 or S, R1 is hydrogen, fluorine, chlorine, bromine, or represents one of the radicals -R6, -O- R6, -SR6, -SO-R6 or -S02R6, R2 means hydrogen, hydroxy, amino or means one of the radicals -R6, -O-R6 or -N = CR6R7, R3 means hydrogen, fluorine, chlorine, bromine, means straight chain or branched chain alkyl having 1 to 3 carbon atoms or straight chain or branched chain halogen alkyl having 1 to 3 carbon atoms and 1 to 3 same or different halogen atoms - especially fluorine or chlorine - R4 means hydrogen, means alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group or means one of the radicals -R6, -O-R6, -S-R6, -NH-R6 or -NR6R7, R5 means amino, hydroxy or means one of the radicals -R6 or -NR6R7, R6 means alkyl having 1 to 6 carbon atoms, straight-chain or branched-chain, substituted on the in a given case, cyano, carboxy, carbamoyl, thiocarbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl alkoxycarbonyl, N-alkylaminocarbonyl, N, N-dialkylaminocarbonyl, trialkylsilyl or alkylsulfonylaminocarbonyl, respectively of chain, are preferred as substituents; linear or branched chain, with respectively 1 to 4 carbon atoms in the individual alkyl or heterocyclyl groups, meaning as the heterocyclyl radical a heterocycle with 5 or 6 members, saturated or unsaturated with 1 to 3 identical or different heteroatoms -especially nitrogen, oxygen and / or sulfur; R > 6b also means haloalkanoalkyl. straight chain or branched chain, with 1 to 4 carbon atoms and 1 to 3 identical or different halogen atoms, especially fluorine, chlorine or bromine. R6 also means alkenyl or alkynyl with 2 to 6 carbon atoms, each optionally substituted one to three times, in the same or different manner by halogen, especially fluorine, chlorine or bromine; R6 also represents cycloalkyl having 3 to 6 carbon atoms, optionally substituted by one to three times, in the same or different manner by halogen, especially fluorine, chlorine or bromine and / or straight-chain or branched-chain alkyl with 1 to 3 carbon atoms; R6 further denotes phenyl, phenylalkyl or phenoxyalkyl respectively substituted, if appropriate, in the phenyl part from one to three times, in the same or different ways, optionally with 1 to 3 carbon atoms in the straight-chain alkyl part or branched chain or means a heterocyclic moiety of 5 to 6 members, saturated or unsaturated, optionally substituted one to three times, in the same or different forms and / or benzo-ring, with 1 to 3 identical or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, being especially preferred as substituents of phenyl or heterocyclyl: fluorine, chlorine, bromine, cyano, nitro, amino, N-acetyl-amine, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, respectively straight-chain or branched chain, with 1 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or halogenoalkylsulfoyl, respectively straight-chain or branched chain with 1 to 4 carbon atoms and 1 to 3 same or different halogen atoms ( especially fluoro or chloro), alkoxycarbonyl or alkoxyiminoalkyl, respectively straight-chain or branched chain, respectively having 1 to 4 carbon atoms in the individual alkyl groups and phenyl, optionally substituted one or more times, in the same or different manner by halogen and / or by alkyl or by straight-chain or branched-chain alkoxy with 1 to 4 carbon atoms and / respectively or by halogenoalkyl or by straight-chain or branched chain halogenoalkoxy having 1 to 4 carbon atoms and 1 to 3 same or different halogen atoms; R7 denotes hydrogen or means alkenyl with 1 to 4 carbon atoms, straight chain or branched chain, optionally substituted, with substituents being particularly preferred: cyano, carboxy, carbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl alkylsulfonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl, trialkylsilyl or alkyl-sulfonylaminocarbonyl respectively straight-chain or branched chain, respectively 1 to 4 carbon atoms in the individual alkyl or heterocyclyl groups, meaning as the heterocyclyl radical a 5- or 6-membered heterocycle, saturated or unsaturated, with 1 to 3 identical or different heteroatoms -especially nitrogen, oxygen and / or sulfur-; R7 further denotes straight chain or branched chain halocarboxyles with 1 to 4 carbon atoms and 1 to 3 same or different halogen atoms - especially fluorine or chlorine. R7 further denotes alkenyl or alkynyl with 2 to 4 carbon atoms, each optionally substituted one to three times, in the same or different manner by halogen, especially fluorine, chlorine or bromine; R7 also represents cycloalkyl with 3 to 6 carbon atoms, optionally substituted one to three times, in the same or different manner by halogen, especially fluorine or chlorine, and / or straight-chain or branched alkyl. with 1 to 3 carbon atoms. Very particularly preferred are the compounds of the formula (I), in which Q 1 and Q 2 are respectively O, R 1 is hydrogen, chlorine, bromine, or represents one of the radicals -R 6, -O-R 6, -S-R 6, -SO-R6 or -S02R6, R2 means hydrogen or means one of the radicals -R6 or -O-R6, R3 means hydrogen, fluorine or chlorine, R4 means hydrogen or means one of the radicals -R6, -O-R6, -S-R6 -NH-R6 or -NR6R7, R5 means one of the radicals -R6 or -NR6R7, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively, optionally once or twice, as substitutes: cyano, carboxy , carbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl, trialkylsilyl or alkylsulfonylaminocarbonyl respectively straight-chain or branched chain, respectively 1 to 4 carbon atoms in the individual alkyl portions; R6 further denotes haloalkyl with 1 to 2 carbon atoms and 1 to 3 same or different halogen atoms - especially fluorine or chlorine; R6 also means alkenyl or alkynyl with 2 to 5 carbon atoms, each optionally substituted once or twice by halogen, especially fluorine or chlorine, R6 is furthermore cyclopropyl, cyclopentyl or cyclohexyl optionally substituted once or twice, Likewise or in different forms by fluorine, chlorine, methyl and / or ethyl, R6 also represents phenyl, benzyl, furyl, thienyl or isoxazolyl substituted, if appropriate, one, two or three times in a the same or in different forms, with fluorine, chlorine, bromine, cyano, nitro, amino, N-acetyl-amine, methyl, ethyl, n- or i-propyl, n-, i- being particularly preferred as substituents respectively; s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, methylsulphinyl, methylsulfonyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy , trifluoromethylthio, trifluoromethyl-sulphonyl, trifluoromethylsulfonyl, methoxy arbonyl, ethoxycarbonyl, methoxyiminomethyl, methoxyiminoethyl, ethoxyiminomethyl, ethoxyiminoethyl, R7 means hydrogen or means methyl, ethyl, n- or i-propyl, n- or i-butyl respectively monosubstituted, if appropriate, as substituents: cyano, carboxyl, Carbamoyl, alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl respectively straight-chain or branched chain with respectively 1 to 4 carbon atoms in the groups I rent; R7 further denotes haloalkyl with 1 or 2 carbon atoms and 1 to 3 same or different halogen atoms - especially fluorine or chlorine; R7 further denotes alkenyl or alkynyl with 2 to 5 carbon atoms, each optionally substituted once or twice by halogen, especially fluorine or chlorine, or R7 is furthermore cyclopropyl, cyclopentyl or cyclohexyl optionally substituted once or twice, in the same or different ways by fluorine, chlorine, methyl and / or ethyl. The definitions of the residues indicated above in a general manner or indicated in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting materials or intermediate products necessary respectively for the obtaining. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated. If, for example, 2- (2-chloro-4-cyano-5-ethylsulfonylamino-phenyl) -5-chloro-4-methyl-2,4-dihydro-3H-1, 2,4- is used; triazol-3-one and pivaloyl chloride as starting materials, the development of the reaction in the case of the process according to the invention can be schematized by means of the following formula scheme: The phenyltriazolin (thio) onas, to be used as starting materials in the case of the process according to the invention for the preparation of the compounds of the formula (I), are defined in general by means of formula (II). In the formula (II), Q1, R1, R2, R3 and R5 preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably for Q1., R1, R2, R3 and R5 in relation to 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 EP 609734 / US 5464810). The halogen (thio) carbonyl compounds, to be used as starting materials in addition in the process according to the invention for the preparation of the compounds of the formula (I), are generally defined by means of the formula (III). In the formula (III), Q2 and R4 preferably have or especially those meanings which have been previously mentioned in a preferred manner or, more particularly, in Q2 and R4 in relation to the description of the compounds according to the invention of the formula (I); in this case X preferably means fluorine, chlorine or bromine, especially chlorine. The starting materials of the formula (III) are chemical products for known organic synthesis. The usual inorganic or organic bases are generally used as reaction auxiliaries for carrying out the process according to the invention. 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 amide. or of calcium, sodium, potassium or calcium carbonate, sodium or potassium bicarbonate or calcium, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate , ethanolate, n- or i-propane-lato, n-, i- s- or sodium or potassium t-butanolate; furthermore, basic organic nitrogenous compounds such as, for example, trimethylamine, triethylamine, tripro-naphne, tributylamine, methyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl-amine, N, N-dimethyl-aniline. , N, N-dimethyl-benzylamine, 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 for carrying out the process according to the invention are, in particular, inert organic solvents. Aliphatic, alicyclic or aromatic halogenated hydrocarbons, for example benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, are especially suitable. carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorustriamide; esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethylsulfoxide. 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 100 ° C, preferably between 10 ° C and 80 ° C. The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under a higher pressure or at a lower pressure, generally between 0.1 bar and 10 bar. For carrying out the process according to the invention, the starting materials are generally used in approximately equimolar quantities. However, it is also possible to use one of the components in a 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 added. In general, it agitates for several hours at the necessary temperature. The preparation is carried out according to usual methods (see the preparation examples). 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 weeds of the following types: Sinapis, Lepi-dium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca , Xanthium, Convolvulus, Ipo oea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanu, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum Cultures of dicotyledonous classes; Gossypium, Gly-cinema, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipo oea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleu, Poa, Festuca, Eleusi-ne, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbrist lis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dac-tyloctenium, Agrotis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active products according to the invention is not, however, limited in any way to these classes, but extends in the same way also over 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, the compounds can be used to control weeds in permanent crops, for example, in forest installations, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, Te from the rubber tree, from oil palms, from cocoa, from berries and hops, on 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 dicotyledonous weeds in monocotyledonous and dicotyledonous crops both in the pre-emergence procedure and in the post-emergence process. The active compounds can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as i-cro-encapsulated 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. In the case of using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: 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, crude petroleum fractions, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cycohexanone, strongly polar solvents, 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, ata-pulgite, montmorillonite or diatomaceous earth and molten synthetic minerals, such as highly dispersed silicic acid, aluminum oxide 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 granules of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; as emulsifiers and / or foam generators, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulphates, aryl sulfonates, and albumin hydrolysis products; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and synthetic phospholipids can be used in the formulations. 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, may 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 formulations or tank mixtures. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Allo-xydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron ( -methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Biala-phos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Buta-chlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlori uron (-ethyl), Chlornitrofen , Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfa uron, Cycloxydim, Cyhalofop (-butyl), 2,4-D , 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dmitramme, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, C ' EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop-ethyl, Framprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-me- -L-tyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumi-chlorac (- pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupro-pacil, Flurenol, Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop ( -ethoxyethyl) -Hexa-zinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapy-rifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metsulfu-ron (-methyl), Metribuzin, Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orben-carb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendime-thali n, Phenmedipham, Piperophos, Pretilachlor, Primisulfu-rum (-methyl), Prometryn, Propachlor, Propanil, Propaquiza-fop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium ), Quinchlorac, Quinmerac, Quizalofop - (- ethyl), Quizalofop (-p-tefuril), Rimsulfuron, Sethoxydim, Simazine, Si etryn, Sulcotrione, Sulfentrazone, S? Lfometu-ron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazi-ne, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Thiocarba-zil, Tralkoxydim, 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, nutrient products for plants and agents that improve the structure of the soil. The active compounds can be used as tails, 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 granules. The application is carried out in the usual manner, for example by watering, atomising, pulverizing, 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. Examples of obtaining. Example 1.

A solution of 0.4 g (5 mmol) of acetyl chloride in 20 ml of acetonitrile is added, dropwise, at room temperature (about 20 ° C) under stirring, to a mixture consisting of 2.0 g of acetonitrile. - (4-cyano-5-ethylsulfonylamino-2-fluoro-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1, 2,4-triazol-3-one, 0.50 g ( 5 mmole) of triethylamine and 40 ml of acetonitrile and the reaction mixture is stirred for 4 hours at room temperature. Then another 0.2 g of acetyl chloride and another 0.25 g of triethylamine are added and the mixture is stirred for another 15 hours at room temperature. After dilution with ice water to approximately twice the volume, it is acidified with acid 2N hydrochloric acid and then shaken with methylene chloride. The organic phase is separated, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is stirred with water and the crystalline product precipitated in this case is isolated by suction filtration. 1.8 g (82% of theory) of 2- [5- (N-acetyl-N-ethylsulphonylamino) -4-cyano-2-fluoro-phenyl] -4-methyl-5-trifluoromethyl-2 are obtained. , 4-dihydro-3H-l, 2,4-triazol-3-one with a melting point of 179 ° C. In a manner analogous to that of Example 1, and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) indicated in Table 1 below.

Table 1: Examples of compounds of the formula (I) 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. After 24 hours, the soil is irrigated with the preparation of active product in such a way that the quantity of active product per unit area is respectively applied. The concentration of the spray liquors is chosen in such a way that it is applied, 1. 000 liters of water / ha, the amount of active product desired in each case. After three weeks, the degree of damage of the plants compared to the development of the untreated controls is evaluated in%. They mean: 0% = no effect (same as untreated controls) 100% = total destruction.

In this test they show, for example, the application rates between 15 g and 60 g / ha, the compounds according to the preparation examples 2, 3 and 8, with a good compatibility with crop plants, such as corn, soybeans and wheat (respectively 0%), a very potent effect against weeds such as Abutilon (100%), Amaranthus (100%), Chenopodium (100%), Datura (100%), Alopecurus (100%), Galium (100%), Matricaria (100%), Stellaria (100 I) and Verónica (90 to 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 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 amounts 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 essay show, for example, to the application amounts between 15 g and 60 g / ha, the compounds according to the preparation examples 2, 3 and 8, with a good compatibility with the crop plants, such as barley and wheat (respectively %), a very potent effect against weeds such as Amaranthus (100%), Chenopodium (100%), Galium (98 to 100%), Lamium (100%), Stellaria (100%) and Veronica (98 to 100). %). 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 (6)

1. CLAIMS Having described the invention as above, property is claimed as contained in the following claims: 1.- Phenyltriazolin (tio) onas of the general formula
2. (I) characterized because;
3. Q1 and Q2 are the same or different and mean 0 or S, R1 means hydrogen, cyano, halogen, or means one of the radicals -R6, -O-R6, -SR6, -SO-R6 or -S02-R6, R2 means hydrogen, hydroxy, amino, or means one of the radicals -R6, -O-R6 or -N = CR6R7, R3 signifies hydrogen, halogen, alkyl or haloalkyl, R4 signifies hydrogen, means alkoxycarbonyl, or signifies one of the residues -R6, -O-R6, -SR6, -NH-R6 or -NR6R7, R5 means amino, hydroxy or means one of the remains
4. -R6 or -NR6R7, R6 means a radical, respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, aryloxyalkyl, arylalkoxyalkyl, heterocycle or heterocyclylalkyl, and R7 is hydrogen or a residue, respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl or cycloalkyl. 2. Process for obtaining phenyltriazolinium (thio) -ones of the general formula (I) wherein Q1, Q2, R1, R2, R3, R4 and R5 have the meanings indicated in claim 1, characterized in that phenyltriazo-lin (thio) -ones of the general formula (II) are reacted wherein Q 1, R 1, R 2, R 3 and R 5 have the meanings given above, with halogen (thio) carbonyl-co compounds of the general formula
5. (III) R < A. (III) * 'in which Q2 and R4 have the meanings indicated above, and X means halogen, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent. 3. Herbicidal agent, characterized in that it has a content in at least one phenyltriazolin (thio) -one of the formula (I) according to claim 1. 4. - Process for the control of undesirable plants, characterized in that the plants are allowed to act undesirable and / or on their environment phenyl triazolin (thio) ornas of the formula (I) according to claim 1. 5. Use of phenyltriazolin (thio) -ones of the formula (I) according to claim 1, for the fight against undesirable plants.
6. 6. Process for the preparation of herbicidal agents, characterized in that phenyltriazo-lin (thio) -ones of the formula (I) according to claim 1 are mixed with extenders and / or surfactants. SUMMARY OF THE INVENTION The invention relates to novel phenyltriazo-lin (thio) -ones of the general formula (I) where Q1 and Q2 are the same or different and mean O or S, R1 means hydrogen, cyano, halogen, or means one of the radicals -R6, -O-R6, -SR6, -SO-R6 or -S02-R6, R2 means hydrogen, hydroxy, amino, or means one of the radicals - R6, -O-R6 or -N = CR6R7, R3 means hydrogen, halogen, alkyl or haloalkyl, R4 means hydrogen, means alkoxycarbonyl, or means one of the radicals -R6, -O-R6, -SR6, -NH-R6 or -NR6R7, R5 means amino, hydroxy or means one of the radicals -R6 or -NR6R7, R6 means a radical, respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, aryloxyalkyl , arylalkoxyalkyl, heterocycle or heterocyclylalkyl, and R <7> signifies hydrogen or means a moiety, respectively substituted, if appropriate, of the series consisting of alkyl, alkenyl, alkynyl or cycloalkyl, a process for its preparation and its use as herbicides.