WO2004048348A1 - Substituted 2-aryl-1,2,4-triazine-3,5-di(thi) ones used as herbicides - Google Patents

Abstract

The invention relates to substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of general formula (I), in which Q<1>, Q<2>, R<1>, R<2>, R<3>, R<4>, R<5> and R<6> are defined as cited in the description, to a method for their production and to their use as herbicides.

Description

SUBSTITUTED 2-ARY-1, 2, 4-TRIA ZIN-3, 5-DI (THI) ONE AS HERBICIDES

The invention relates to new substituted 2-A-l-l, 2,4-triazm-3,5-di (thi) one, processes for their preparation and their use as herbicides.

It is known that certain substituted 2-aryl-l, 2,4-triazm- (thi) one have herbicidal properties (cf. EP 011 693 AI, EP 271 170 A2, WO 86/00072 AI, WO 97/30980 AI , WO 00/75119 A2, US 4,755,217 A, US 4,878,941 A, US 4,956,004 A, US 5,262,390 A, US 5,344,812 A). The from the specified

However, patent applications or patents known to patents have not gained any significant significance.

New substituted 2-A-l-l, 2,4-tri-zm-3,5-di (thi) ones of the general formula (I)

in which

Q ^{1 represents} oxygen or sulfur,

Q ^{2 represents} oxygen or sulfur,

R ¹ for hydrogen, cyano, amino, for alkyl, alkoxy, AJ-ylamino, di-, optionally substituted in each case by cyano, halogen or C 1 -C 4 -alkoxy all-ylamino, alkylcarbonyl or alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, AJDnylcarbonyl or alkynyloxycarbonyl, each with 2 to 6 carbon atoms in the alkenyl or Alkynyl groups, or cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part,

R ² for hydrogen, halogen, nitro, carboxy, cyano, thiocarbamoyl, amino, for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each with 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or C 4 -C alkoxy, for in each case optionally substituted by halogen, alkenyl, alkenyloxy, alkenylthio, AJ-inyl, alkynyloxy or alkynylthio each having 2 to 6 carbon atoms in the

Alkenyl or alkynyl groups, or for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C 1 -C 4 -al yl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 6 carbon atoms in the alkyl part,

R ^{3 represents} hydrogen, cyano or halogen,.

R ^{4 represents} halogen,

R ⁵ for hydrogen, for alkoxycarbonyl having 1 to 6 carbon atoms in the

AKkoxygruppe, or for one of the radicals -R ⁷ , -OR ⁷ , -SR ⁷ , -NH-R ⁷ or -NR ⁷ R ° -,

R ^{6 represents} amino, hydroxy or one of the radicals -R ⁷ or -NR ⁷ R ⁸ , R ^{7 represents} optionally mono- or polysubstituted, identically or differently substituted, straight-chain or branched alkyl having 1 to 10 carbon atoms, the following being suitable as substituents:

Cyano, carboxy, carbamoyL thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylcarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-all-1-aminocarbonyl, N, N-di-il-yl-aminocarbonyl, or trialkylsulfonylyl each with 1 to 6 carbon atoms in the individual alkyl parts, or heterocyclic, the heterocyclyl radical being a five- to seven-membered, optionally benzene-fused, saturated or unsaturated heterocycle with 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - stands, or

R ^{7 represents} in each case optionally mono- or polysubstituted, identically or differently, alkenyl or alkynyl substituted by halogen or phenyl, each having 2 to 8 carbon atoms, or

R ⁷ for cycloalkyl which is optionally monosubstituted or polysubstituted, identically or differently, by cyano, halogen and / or C ₁ -C ₄ alkyl

Cycloalkylalkyl each having 3 to 7 coolant atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or

R ⁷ for aryl, in each case optionally in the aryl part, mono- or polysubstituted by identical or different substituents. Arylalkyl, aryloxyalkyl or arylalkoxyalkyl, each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, or for an optionally mono- or polysubstituted, identically or differently and / or benzannellated, saturated or unsaturated, heterocyclyl radical or heterocyclylalkyl radical having five to seven carbon atoms in the heterocycle and 1 to 4 carbon atoms in the alkyl part and with 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -, the following being suitable as aryl or heterocyclyl substituents:

Halogen, cyano, nitro, amino, N- (C ₁ -C ₄ -alkyl-carbonyl) -amrno, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, Haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, singly or multiply, identically or differently by halogen and / or straight-chain or branched alkyl or alkoxy, each with 1 to

6 carbon atoms and / or straight-chain or branched haloalkyl or haloalkoxy each having 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms substituted phenyl, and

stands for hydrogen or for optionally mono- or polysubstituted, identically or differently substituted, straight-chain or branched alkyl having 1 to 8 carbon atoms, the following being suitable as substituents:

Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, A-alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl or alkylsulfonylaminocarbonyl in each case with 1 to 8 alkyllyl radicals, where the heterocyclic radical is a five- to seven-membered, optionally benzene-fused, saturated or unsaturated heterocycle with 1 to 3 identical or different which are heteroatoms - in particular nitrogen, oxygen and or sulfur -, or

R ⁸ for each optionally single or multiple, identical or different, halogen-substituted alkenyl or alkynyl each having 2 to 8

Carbon atoms, or

R ^{8 stands} for cycloalkyl with 3 to 7 carbon atoms which is optionally substituted once or several times, identically or differently, by cyano, halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, or

R ⁸ with R ^{7 represents} alkanediyl (alkylene) having 2 to 6 carbon atoms which is optionally interrupted by O (oxygen), S (sulfur), NH or N (C 1 -C ₄ -alkyl),

found.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are defined below.

Q ¹ preferably represents oxygen.

Q ² preferably represents oxygen.

R ¹ preferably represents hydrogen, cyano, amino, methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Ethoxy, n- or i- propoxy, n-, i-, s- or t-butoxy, me ylamino, e ylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, Dimethylamino, the ylamino, acetyl,

Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, for propenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propenyloxycarbonyl, butenyloxycarbonyl, optionally substituted by fluorine, chlorine or bromine, for propynyl, butynyl, propynylcarbonyl, butynylcarbonyl, propynyloxycarbonyl or butynyloxycarbonyl, or for each optionally substituted by cyano, fluorine, chlorine, Bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.

R ² preferably represents hydrogen, nitro, carboxy, cyano, thiocarbamoyl,

Amino, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy, n which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy - or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylarnino, ethylamino, n - or i-Propylamino, n-, i-, s- or t-butylamino, diniethylamino or die ylamino, for propenyl, propenyloxy, propenylthio, butenyl, butenyloxy or butenylthio, each optionally substituted by fluorine, chlorine or bromine, for propynyl , Propynyloxy, propynylthio, butynyl, butynyloxy or butynylthio, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl.

R ³ preferably represents hydrogen, fluorine or chlorine.

R ⁴ preferably represents fluorine, chlorine or bromine.

R ⁵ preferably represents hydrogen, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or one of the radicals -R ⁷ , -OR ⁷ , -SR ⁷ , -NH-R ⁷ or -NR ⁷ R8. R ⁶ preferably represents methyl, ethyl or n- or i-propyl which is optionally mono- or disubstituted by fluorine.

R ⁷ preferably stands for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo, each optionally substituted once or twice -Pentyl, n-, i- or s-hexyl, the substituents in each case preferably being:

Cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, acetylmethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, trimethylsilyl, methylsulfonylaminocarbonyl or ethylsulfonylaminocarbonyl.

R ⁷ furthermore preferably represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl which is optionally mono- or disubstituted by fluorine and / or chlorine or phenyl.

R ⁷ furthermore preferably represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl which is optionally substituted once or twice, identically or differently, by fluorine, chlorine, methyl and / or ethyl. Cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl or cyclohexylethyl.

R ⁷ furthermore preferably represents phenyl, benzyl, phenylethyl which is optionally mono-, di- or trisubstituted in the same or different ways,

Phenylpropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, furyl, furylmethyl, thienyl benzothienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl,

Oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyrirmdinyl, Pyrrolidinyl, piperidinyl, morpholinyl, 1,3-benzodioxolylmethyl or chromanyl, where the following are preferred as substituents:

Fluorine, chlorine, bromine, cyano, nitro, -A-mino, N-acetylamino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, methylene sulfinyl, methylsulfonyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromoxycarbonyl carbonyl, meth Methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl, phenyl mono- or disubstituted by chlorine or fluorine.

R ⁸ preferably represents hydrogen or, in each case optionally methyl, ethyl, n- or i-propyl, n- or i-butyl, where the substituents are preferably:

Cyano, carboxyl, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethyliminocarbonyl, Dimemylaπiinocarbonyl.

R ⁸ furthermore preferably represents ethenyl propenyl, butenyl, which is optionally mono- or disubstituted by fluorine and / or chlorine,

Ethynyl, propynyl or butynyl.

R ⁸ furthermore preferably represents cyclopropyl, cyclopentyl or cyclohexyl which may be mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl. R ⁸ further preferably together with R ^{7 represents} butane-1,4-diyl, pentane-1,5-diyl or 3-oxapentane-l, 5-diyl.

R ¹ particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine.

R ² particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine.

R ³ particularly preferably represents fluorine or chlorine.

R ⁴ particularly preferably represents chlorine or bromine.

R ⁵ particularly preferably represents hydrogen or one of the radicals -R ⁷ ,

-OR ⁷ , -SR ⁷ -NH-R ⁷ or -NR ⁷ RS.

R ⁷ particularly preferably represents in each case optionally mono- or disubstituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo- Pentyl, the substituents in each case preferably being:

Cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxy-methoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, acetyloxymethyl, acetylrnethoxy.

R ⁷ furthermore particularly preferably represents ethenyl, propenyl, ethynyl or propynyl which is optionally mono- or disubstituted by fluorine and / or chlorine or phenyl. Furthermore, R ⁷ particularly preferably represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl or cyclohexylethyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl.

R ⁷ furthermore particularly preferably represents phenyl, benzyl, phenylethyl, phenylpropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, furyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, optionally substituted once, twice or three times, identically or differently.

Oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrrolidinyl, piperidinyl, 1,3-benzodioxolylmethyl or chromanyl, where the following are preferably used as substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, methylthio, Ethylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, 2-chlorophenyl or 2,6-dichlorophenyl.

R ⁸ particularly preferably represents hydrogen or in each case optionally substituted methyl, ethyl, n- or i-propyl, n- or i-butyl, the following being preferred as substituents:

Cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy.

R ⁸ furthermore particularly preferably represents in each case monosubstituted or disubstituted by fluorine and / or chlorine-substituted ethenyl, propenyl, butenyl, etiinyl, propynyl or butynyl. R ⁸ furthermore particularly preferably represents cyclopropyl, cyclopentyl or cyclohexyl which may be mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl.

R ¹ very particularly preferably represents methyl or ethyl which is optionally substituted by fluorine.

R ² very particularly preferably represents hydrogen or methyl or ethyl which is optionally substituted by fluorine.

R ⁵ very particularly preferably represents methyl, ethyl or n- or i-propyl which is optionally mono- or disubstituted by fluorine or chlorine,

for ethenyl or propenyl optionally substituted by fluorine and / or chlorine or phenyl,

for cyclopropyl, cyclopentyl or cyclohexyl optionally substituted once or twice, identically or differently, by fluorine, chlorine, methyl and / or ethyl,

for benzyl, phenylethyl, furyl, thienyl, benzothienyl, oxazolyl, isoxazolyl or 1,3-, each optionally substituted by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, 2-chlorophenyl or 2,6-dichlorophenyl Benzodioxolylmethyl.

The general or residual radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges. Those compounds of the formula (I) which have a combination of the meanings listed above as preferred are preferred according to the invention.

Those compounds of the formula (I) in which a combination of the meanings listed above as particularly preferred are present are particularly preferred according to the invention.

According to the invention, those Nerbindungen are particularly preferred

Formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are in each case straight-chain or branched as far as possible, also in conjunction with heteroatoms, such as in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.

The new substituted 2-aryl-l, 2,4-1ri - zm-3,5-di (thi) one of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.

The new substituted 2-atyl-l, 2,4-triazm-3,5-di (tbi) one of the general formula (I) is obtained if 2-aryl-l, 2,4-triazine-3,5 -di (thi) one of the general formula (II)

in which

Q ¹ , Q ² , R ¹ , R ² , R ³ , R ⁴ and R ^{6 have} the meaning given above,

with halocarbonyl compounds of the general formula (III)

in which

R ^{5 has} the meaning given above and

X represents halogen,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a ner diluent.

If, for example, 2- (4-bromo-2-fluoro-5-methylsulfonylamino-phenyl) -4-methyl-l, 2,4-triazine-3,5 (2H, 4H) -dione and propionic acid chloride are used as starting materials, then the course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the 2-aryl-1,2,4-triazine-3,5-di (thi) ones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (H), Q, Q, R, R, R, R and R preferably have those meanings which are already preferred, particularly preferred or in particular in connection with the description of the compounds of the general formula (I) according to the invention have preferably been given for Q ¹ , Q ² , R ¹ , R ² , R ³ , R ⁴ and R ⁶ .

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. WO 86/00072 A; ACS Symp. Ser. (1992), 504 [Synth. Chem. Agrochem. III, 134 -136]; Manufacturing examples).

Formula (III) provides a general definition of the halocarbonyl compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (HI), R ⁵ preferably or in particular has the meaning which has already been given as preferred, particularly preferred or very particularly preferred for R ⁵ in connection with the description of the compounds of the general formula (I) according to the invention is; X preferably represents fluorine, chlorine or bromine, especially chlorine. The starting materials of the general formula (UT) are known organic synthetic chemicals.

The usual inorganic or organic bases or acid acceptors are generally used as reaction aids for the process according to the invention

Consideration. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride,

Lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, i or t butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triemylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, emyl-cyclohexylamine, N, N-dimethylaniline, N, N- Dimethyl benzyl imine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl ρyridine, 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).

Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention. Examples of such catalysts are:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetjaoctylammonium chloride, tetrabutylammonium hydrogen sulfate, memyl trioctylammomium chloride, hexadecyl-tr-methylammonium chloride, hexadecyl-trin ethylammonium-zammidium-ammonium-bromidium-ammonium-bromide-bromide, chloride, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyl tributylammorium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, butyl triphenylphosphonium chloride, Ernyl trioctylphosphoriium bromide, tetraphenylphosphonium bromide.

In addition to water, suitable diluents for carrying out the process according to the invention are, above all, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether,

Dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as

Dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° 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 elevated or reduced pressure - generally between 0.1 bar and 10 bar. To carry 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 a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, in particular, as original plant legifiers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether 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 e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,

Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Plantaago, Pharb Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,

Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriochaimis, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,

Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the active compounds according to the invention for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for selective use

Control of monocot and dicot weeds in monocot and dicot crops, both pre- and post-emergence.

In certain concentrations or application rates, the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. They can be if used as intermediates or precursors for the synthesis of other active ingredients.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by

Plant variety rights of protectable or non-protectable plant varieties. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or

Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.

The active ingredients can be converted into the usual formulations, such as

Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances. These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as

Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents are possible: e.g. non-ionic and anionic

Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the moldings. Other additives can be mineral and vegetable oils.

It possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin _dyestuffs. Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations in a mixture with known herbicides and / or with substances which improve crop tolerance ("safeners") for weed control, finished formulations or tank mixes being possible. Mixtures are also possible possible with unauthorized agents which contain one or more known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (beflubutamide, ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl) , Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetarnide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidone (-ethyl), Cinmethyl, Clefoximuron, Cinosulfur , Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Clor-ansulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2 , 4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethamamidyn, Dimethyamid , Dinitramine, Diphenarnid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Emofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Fentrazamide -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,

Flufenpyr, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Fluprop-acil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-flurene), , Fluroxypyr (-butoxypropyl, -meptyl), fluorideol, Flurtamone, Fluthiacet (-methyl), Fluthimide, Fomesafen, Foramsulfiiron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop ( -ethoxyethyl, -P-methyl), hexazinones, imazamethabenz (-methyl), imazamethapyr, lnazamox, imazapic, imazapyr, imaza- quin, imazethapyr, -mazosulfuron, iodosulfuron (-methyl -sodium), ioxynil, iso-propalin, isopro Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Ketospiradox, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotione, Metamitron, Metazachlor, Methabei-zthiazuron, Metobenzuron, Metoblora- uram, (Metoblora-) urol Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproaniüde , Napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazafen, pipoxoxamidone, pethoxamidone, pethoxamidone, pethoxamide, pethoxamide, pethoxamide, pethoxamidone - tilachlor, Primisulfuron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolonate, Pyrazolonate , Pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid,

Pyrirninobac (methyl), pyrithiobac (sodium), quinchlorac, quinmerac, quin oclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfirron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxzine, Terbuthylazine, Then , TMafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tri-diphane, trifluralin, trifloxysulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron.

Known safeners are also suitable for the mixtures, for example

AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-

24, dichlormid, dymron, fenclorim, fenchlorazole (-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29,148th

A mixture with other known active ingredients, such as fungicides,

Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners are possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

As already mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, wild plant species and plant cultivars and their parts, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, optionally in combination with conventional methods (Genetically

Modified Organisms) and their parts. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the spectrum of activity and / or an enhancement of the effect of the substances and agents which can be used according to the invention - also in combination with other agrochemicals

Active ingredients, better growth of crops, increased tolerance of crops to high or low temperatures, increased tolerance of crops to dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the crop, higher Shelf life and / or workability of the harvested products possible, which go beyond the effects to be expected.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.

The traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a), CryIA (b), CryΙA (c), CryDA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The traits that are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imide azolinones, sulfonylureas, glyphosate or phosphinothricin (eg "PAT" gene). The genes conferring the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YTELD GARD® (eg

Corn, Cotton, Soybean), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soybeans), Liberty Link® (tolerance to

Phosphinothricin, e.g. Rapeseed), EVH® (tolerance to l-midazolinone) and STS® (tolerance to sulfonylureas e.g. maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be treated according to the invention particularly advantageously with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Preparation Examples:

Example 1:

407 mg (1.0 mmol) of 2- (4-bromo-2-fluoro-5-e ylsulfonylaminophenyl) -4-methyl-l, 2,4-triazine-3,5 (2H, 4H) -dione and 172 mg (1.7 mmol) of Triemyla in are mixed with 157 mg (1.5 mmol) of 2,4-difluorophenyl-propionic acid chloride in 15 ml of 1,2-dichloroethane and the mixture is stirred at 25 ° C. for 12 hours. 10 ml of 10% hydrochloric acid are then added, the organic phase is filtered through a Whatman cartridge and concentrated on a rotary evaporator.

281 mg (49% of theory) of 2- [5- (N-2,4-difluorophenyl-propionyl-N-emylsulfonylam o) -4-bromo-2-fluorophenyl] -4-memyl-1 are obtained , 2,4-triazine-3,5- (2H, 4H) - dione. Melting point: 179 ° C, log P: 3.37 ^a) .

Example 2:

407 mg (1 mmol) of 2- (4-bromo-2-fluoro-5-e ylsulfonylaminophenyl) -4-methyl-1,2,4-triazine-3,5 (2H, 4H) dione and 172 mg (1.7 mmol) of triethylamine in 15 ml of 1,2-dichloroethane are mixed with 307 mg (1.5 mmol) of 2-methoxy-phenyl-propionic acid chloride and the mixture is stirred at 25 ° C. for 12 hours. Then 10 ml of 10% hydrochloric acid are added, the organic phase is filtered through a Whatman cartridge, concentrated and purified by preparative HPLC under the following conditions:

Preparative conditions: Kromasil 100 C18 16μm 250 * 50mm; Acetonitrile / water 62/38 isocratic, flow: 280 ml / min, UV: 210 nm, injection volume: 0.32 g substance / 15 ml acetonitrile, 10 ml water.

135 mg (24% of theory) of 2- [5- (N-2-methoxy-phenyl-propionyl-N-ethylsulfonylannno) -4-bromo-2-fluorophenyl] -4-memyl-1,2 are obtained. 4-azine-3,5- (2H, 4H) - dione. Melting point: 89 ° C, log P: 3.33 ^a) .

Analogously to Examples 1 and 2 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (High Performance Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous

Phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with a).

(b) Eluents for determination in the neutral range: 0.01 molar aqueous

Phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with b). The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

Starting materials of the formula (ID:

Example (II-l)

step 1

(see DE 199 62 932, example (XI-1)

Level 2

8.914 g (30 mmol) of N- (2-bromo-4-fluoro-5-amo-phenyl) -emanesulfonamide are concentrated in 400 ml of water and 50 ml. Hydrochloric acid was stirred at 40 ° C. for 10 minutes, cooled to 0 ° C., 2.07 g (30 mmol) of sodium nitrite dissolved in 30 ml of water were added dropwise and the mixture was stirred at 0 ° C. for 30 minutes. 20.4 g of sodium acetate trihydrate (150 mmol), dissolved in 80 ml of water, are then added dropwise at 0.degree. This solution is then stirred at 10 ° C. into a further solution of 7.4 g (30 mmol) of malonyl urethane (J. Chem. Soc, 350, (1921), 98.6 g of sodium acetate trihydrate in 1500 ml of water, 60 Stirred minutes, the solid is isolated by suction, washed with water and dried.

14.2 g (85% of theory) of [2 - [[4-bromo-5 - [(ethylsulfonyl) amino] -2-fluorophenyl] hydrazono] -3 - [(ethoxycarbonyl) ammo] -l are obtained, 3-dioxopropyl] carbamic acid ethyl ester. Melting point: 200 ° C, log P: 2.63 ^a) .

level 3

14.2 g (25.6 mmol) [2 - [[4-bromo-5 - [(emylsulfonyl) amino] -2-fluoro-phenyl] hydrazono] -3 - [(ethoxycarbonyl) am o3-l, 3-dioxopropyl] -carbarnidsäure-ethyl ester (product of stage 2) are in 190 g of N, N-Dimemyl-foπnarmd with 5.69 g

(64 mmol) sodium hydroxide stirred for 4 hours at 100 ° C, concentrated on a rotary evaporator, the residue stirred in water, with conc. Acidified hydrochloric acid, extracted with ethyl acetate, the organic phase dried over sodium sulfate and again concentrated on a rotary evaporator. 9.4 g (79% of theory) of 2- [4-bromo-5 - [(ethylsulfonyl) arino] -2-fluorophenyl] -3,5-dioxo-2,3,4,5-tetrahydro are obtained -l, 2,4-triazine-6-carboxylic acid. log P: 0.93 ^a) .

Level 4

22.8 g (52.15 mmol) of 2- [4-bromo-5 - [(emylsulfonyl) amino] -2-fluorophenyl] -3,5-dioxo-2,3,4,5-tetxahydro-l , 2,4-triazine-6-carboxylic acid (product of stage 3) are stirred with 100 ml of mercaptoacetic acid at 140 ° C. for 12 hours, then stirred in 500 ml of water, neutralized by adding sodium hydrogen carbonate, extracted with ethyl acetate, the organic phase over Dried sodium sulfate and. concentrated on a rotary evaporator. The residue is recrystallized from isopropanol.

11.6 g (54% of theory) of 2- [4-bromo-5 - [(emylsulfonyl) amino] -2-fluorophenyl] -3,5-dioxo-2,3,4,5-tetrahydro are obtained -l, 2,4-triazine. Melting point: 204 ° C, log P: 1.40 ^a) . Level 5

22.7 g (57.7 mmol) of 2- [4-bromo-5 - [(ethylsulfonyl) amino] -2-fluorophenyl] -3,5-dioxo-2,3,4,5-tetrahydro-l , 2,4-triazine (product of stage 4) are initially charged with 9.0 g (65.2 mmol) of potassium carbonate in 500 ml of acetonitrile, mixed with 8.17 g (63.5 mmol) of ethanesulfonic acid chloride and added for 12 hours Stirred at 25 ° C. The mixture is then concentrated on a rotary evaporator, the residue is stirred with water and concentrated. Acidified hydrochloric acid, filtered off the precipitated product, washed with water and dried.

23.8 g (76.5% of theory) of N- [2-bromo-5- (3,5-dioxo-4,5-dihydro-1,2,4-triazm-2 (3H) -yl are obtained ) -4-fluorophenyl] -N- (ylsulfonyl) ethanesulfonamide. Melting point: 266 ° C, log P: 2.09 ^a) .

Level 6

23.8 g (44.14 mmol) of N- [2-bromo-5- (3,5-dioxo-4,5-dmydro-l, 2,4-triazin-2 (3H) -yl) -4-fluorine -phenyl] -N- (ethylsulfonyl) -ethanesulfonamide (product of stage 5) in 400 ml of acetonitrile with 6.7 g (48.55 mmol) of potassium carbonate and 6.9 g (48.55 mmol) of methyl iodide for 15 hours at 25 ° C stirred, concentrated on a rotary evaporator, the residue stirred with water, with conc. Acidified hydrochloric acid, filtered off the precipitated product, washed with water and dried.

22 g (94% of theory) of N- [2-bromo-5- (3,5-dioxo-4,5-dihydro-4-methyl-1,2,4-triaz-n-2 (3H) - yl) -4-fluoro-phenyl] -N- (emylsulfonyl) -ethanesulfonamide. Melting point: 294 ° C, log P: 2.5 l ^a) .

Level 7

22 g (41.4 mmol) of N- [2-bromo-5- (3,5-dioxo-4,5-dihydro-4-methyl-l, 2,4-triazine-2 (3H) -yl) - 4-fluorophenyl] -N- (ethylsulfonyl) -eth-msulfonamide (product of stage 6) are stirred with 6.96 g (82.83 mmol) of sodium hydrogen carbonate in 200 ml of acetone and 160 ml of water at 55 ° C. for 12 hours , rotated in on a rotary evaporator, the residue stirred with water, with conc. Acidified hydrochloric acid, filtered off the precipitated product, washed with water and dried.

14.3 g (82% of theory) of 2- (4-bromo-2-fluoro-5-ethylsulfonylaminophenyl) -4-methyl-1,2,4-triazine-3,5 (2H, 4H) are obtained. -dione. Melting point: 227 ° C, log P: 1.80 a)

Example O -2)

step 1

(see WO 86/00072, Ex. 6)

The preparation is carried out analogously to levels 1 to 4 under example (Hl).

In step 1, the product is obtained with a melting point of 203 ° C. (Lit: 202-3 ° C.). log P: 1.68 ^a) .

Level 2

(Cf. WO 86/00072, Ex. 7)

2.0 g (8.28 mmol) of the product of stage 1 are mixed with 1.37 g (9.93 mmol)

Potassium carbonate and 1.41 g (9.93 mmol) of methylhodide in 50 ml of N, N-dimethylformamide were stirred at 25 ° C. for 12 hours, concentrated on a rotary evaporator, the residue was stirred with water, and concentrated. Acidified hydrochloric acid, filtered off the precipitated product, washed with water and dried.

1.8 g (85% of theory) of product of stage 2 are obtained. Melting point: 115 ° C. (Lit .: 114-16 ° C.); log P: 2.14 ^a) . level 3

(WO 86/00072, Compound 46)

1.8 g (7.0 mmol) of product of stage 2 are concentrated in 30 ml. Dissolved sulfuric acid, at 0 ° C with 0.44 g (7.0 mmol) conc. Nitric acid added, stirred for 30 minutes, poured into ice water, filtered off the precipitated product, washed with water and dried.

1.7 g (80% of theory) of product of stage 3 are obtained. Melting point: 140 ° C. (Lit .: 132.34 ° C.), log P: 2.14 ^a) .

Level 4

( ^γ S ^{L W0 86} / ° ⁰⁰⁷² > ^Bs P- ⁴⁷ )

A suspension of 4 ml of water, 20 ml of acetic acid and 1.54 g (27.6 mmol) of iron powder are heated to 80 ° C., stirred at this temperature for 30 minutes, then 1.66 g (5.52 mmol) of product of the step 3, dissolved in 50 ml of ethyl acetate, added dropwise and stirred at 80 ° C for 4 hours. After cooling, it is suctioned off through kieselguhr, the residue is washed with ethyl acetate and with water, the separated organic phase, dried over sodium sulfate and concentrated on a rotary evaporator.

1.2 g (75.5% of theory) of product of stage 4 are obtained. Melting point: 147 ° C. (Lit: 150-52 ° C.), log P: 1.66 ^a) .

Level 5

1.62 g (5.98 mmol) of product of stage 4 and 2.3 g (22.7 mmol) of triethylamine in 50 ml of dichloromethane are mixed with 2.06 g (mmol) of methanesulfonyl chloride, stirred at 25 ° C. for 1 hour, mixed with water, with conc. Acidified hydrochloric acid, the organic phase separated, dried over sodium sulfate and concentrated on a rotary evaporator.

2.72 g (71% of theory) of product of stage 5 are obtained. Log P: 1.99 ^a) . Level ö

2.7 g (6.33 mmol) of product from stage 5 are stirred for 3 hours at 55 ° C. with 1.14 g (1.54 mmol) of sodium hydrogen carbonate in 50 ml of acetone and 25 ml of water, concentrated on a rotary evaporator, the Residue mixed with water, with conc. Acidified hydrochloric acid, extracted with dichloromethane, the organic phase dried over sodium sulfate and concentrated on a rotary evaporator.

1.88 g (85% of theory) of 2- (4-Cωor-2-fluoro-5-methylsulfonylamino-ρhenyl) -4-methyl-l, 2,4-triazine-3,5 (2H, 4H) are obtained. -dione. log P: 1.47 ^a) .

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier 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 sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like uri-treated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 1, 2, 5, 10, 11, 13, 16, 18, 21, 25, 28, 30, 33, 34, 40, 43, 46, 51, 54, 59, 65, 69 and 72 with good tolerance to cultivated plants such as maize, very strong activity against weeds. Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants with a height of 5 - 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

10001 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to the preparation example show

1, 2, 5, 10, 11, 13, 16, 18, 21, 25, 28, 30, 33, 34, 40, 43, 46, 51, 54, 59 and 72 very strong action against weeds.

Claims

Patentansprtiche

1. Compounds of formula (I)

in which

represents oxygen or sulfur,

represents oxygen or sulfur,

R ¹ for hydrogen, cyano, amino, for each optionally substituted by cyano, halogen or C1-C4-alkoxy alkyl, alkoxy, alk lamino, diall-ylamino, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, each optionally halogen-substituted alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynylcarbonyl or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl or alkynyl groups, or for cycloalkyl which is optionally substituted by cyano, halogen or C1-C4-alkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part,

R ² for hydrogen, halogen, nitro, carboxy, cyano, thiocarbamoyl, amino, for each optionally by cyano, halogen or C1-C4- Alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkyl-imino, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or A-lkynylthio optionally substituted by halogen each have 2 to 6 carbon atoms in the alkenyl or

Alkynyl groups, or represents cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C1-C4-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 6 carbon atoms in the alkyl part,

R ^{3 represents} hydrogen, cyano or halogen,

R ^{4 represents} halogen,

R ^{5 represents} hydrogen, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy group, or one of the radicals -R ⁷ , -OR ⁷ , -SR ⁷ , -NH-R ⁷ or -NR ⁷ R ⁸ ,

R ^{6 represents} amino, hydroxy or one of the radicals -R ⁷ or -NR ⁷ R ⁸ ,

R ^{7 represents} optionally mono- or polysubstituted, identically or differently substituted, straight-chain or branched alkyl having 1 to 10 carbon atoms, the following being suitable as substituents:

Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylcarbonyloxy, aikylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N, N-diall-yl-aminocarbonyl or trialkylsulfonylyl in each case 1 to 6 carbon atoms in the individual alkyl parts, or heterocyclyl, with the heterocyclyl radical a five- to seven-membered, optionally benzene-fused, saturated or unsaturated heterocycle with 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -, or

R ^{7 represents} in each case optionally mono- or polysubstituted, identically or differently, alkenyl or alkynyl substituted by halogen or phenyl, each having 2 to 8 carbon atoms, or

R ⁷ represents cycloalkyl or cycloalkylalkyl, each optionally mono- or polysubstituted, identically or differently, by cyano, halogen and / or C ₁ -C ₄ -alkyl, each having 3 to 7 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or

R ^{7 stands} for aryl, arylalkyl, aryloxyalkyl or arylalkoxyalkyl, each of which is mono- or polysubstituted or substituted in the aryl moiety, in each case with 6 to 10 carbon atoms in the aryl moiety and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, or for an optionally mono- or polysilicon moiety , Identically or differently substituted and / or benz-fused, saturated or unsaturated heterocyclyl radical or heterocyclylalkyl radical with five to seven carbon atoms in the heterocycle and 1 to 4 carbon atoms in the alkyl part and with 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - stands, whereby aryl or heterocyclyl substituents come into consideration:

Halogen, cyano, nitro, amino, N- (C ₁ -C ₄ -alkyl-carbonyl) -a-nino, in each case straight-chain or branched alkyl, alkoxy, alkylthio,

Alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoxaminoalkyl each having 1 to 6 carbon atoms in each Alkyl parts and optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl or alkoxy each having 1 to 6 carbon atoms and / or straight-chain or branched haloalkyl or haloalkoxy each having 1 to 6

Carbon atoms and 1 to 3 identical or different halogen atoms substituted phenyl, and

R ^{8 represents} hydrogen or optionally mono- or polysubstituted, identically or differently substituted, straight-chain or branched alkyl having 1 to 8 carbon atoms, the following being suitable as substituents:

Cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, all-ylamonocarbonyl, dialiylaminocarbonyl, trialkylsilyl or AJ-1-ylsomenonyl-8-sulfonylaminocarbonyl the individual alkyl parts or heterocyclyl, the heterocyclyl radical being a five- to seven-membered, optionally benzyl-fused, saturated or unsaturated

Heterocycle with 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -, or

R ^{8 represents} in each case optionally single or multiple, identical or different from halogen-substituted alkenyl or A-alkynyl each having 2 to 8 carbon atoms, or R ^{8 stands} for cycloalkyl with 3 to 7 carbon atoms which is optionally substituted once or several times, identically or differently, by cyano, halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, or

R ⁸ with R ^{7 represents} alkanediyl (alkylene) having 2 to 6 carbon atoms which is optionally interrupted by O (oxygen), S (sulfur), NH or N (-CC ₄ -alkyl).

IU

Compounds of formula (I) according to claim 1, characterized in that

Q ^{1 represents} oxygen,

15

Q ^{2 represents} oxygen,

R ¹ for hydrogen, cyano, amino, for methyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, 0 ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy , n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, dimethylamino , Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyl, butenyl, which is optionally substituted by fluorine, chlorine or bromine,

Propenylcarbonyl, butenylcarbonyl, propenyloxycarbonyl, butenyloxycarbonyl, for propynyl, butynyl, propynylcarbonyl, butynylcarbonyl, propynyloxycarbonyl or butynyloxycarbonyl, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclo, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl - hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ² for hydrogen, nitro, carboxy, cyano, thiocarbamoyl, amino, fluorine, chlorine, bromine, each optionally with cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t -Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, emylamino, n- or i-propylamino, n-, i-, s- or t-butylamino , Dimethylamino or Diemylamino, for propenyl, propenyloxy, propenylthio, butenyl, butenyloxy or butenylthio, each optionally substituted by fluorine, chlorine or bromine, for propynyl, propynyloxy, propynylthio, butynyl, butynyloxy or butynylthio, or for each optionally substituted by cyano, fluorine, chlorine , Bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} fluorine, chlorine or bromine,

R ^{5 represents} hydrogen, methoxycarbonyl, ethoxycarbonyl, n- or i-prop-oxycarbonyl, or one of the radicals -R ⁷ , -OR ⁷ , -SR ⁷ , -NH-R ⁷ or -NR ⁷ R ⁸ ,

R ⁶ represents methyl, ethyl or n- or i-propyl which is optionally mono- or disubstituted by fluorine,

R ⁷ for each optionally mono- or disubstituted

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or is neo-pentyl, n-, i- or s-hexyl, the substituents in each case being:

Cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxymethoxy, ethoxymethoxy, methoxy-ethoxy, ethoxyethoxy, acetylene methoxy, methylthio, ethylthio, n- or i-propylthio, methyl sulfinyl, ethyl sulfinyl , Methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, memylaminocarbonyl, ethyl aminocarbonyl, dimemylaminocarbonyl, trimethylsilyl, methylsulfonylaminocarbonyl, ethylsulfonylaminocarbonyl,

R ⁷ represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally mono- or disubstituted by fluorine and / or chlorine or phenyl,

R ⁷ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl or cyclohexylethyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl,

R ⁷ furthermore represents phenyl, benzyl, phenylethyl, phenylpropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, furyl, furylmethyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, optionally substituted once, twice or three times, identically or differently.

Pyrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrrolidinyl, piperidinyl, morpholinyl, 1,3-benzo-dioxolylmethyl or chromanyl, where the following are preferably used as substituents: Fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, methcarbonyloxymethyloxoxymoxyloxymoxyloxymoxyloxymoxyloxymoxyloxymoxyloxymoxyloxymoxyloxymoxymoxyloxymoxyloxymoxyloxymoxyloxymoxymoxyloxymoxyloxymoxymoxyloxymoxyloxymoxyloxymoxyloxymethyloxymoxymoxyloxymoxymoxyloxymethyloxymoxyloxymoxyloxymoxymoxyloxymoxyloxymoxyloxymoxoxy Ethoximinomethyl, ethoximinoethyl, phenyl substituted once or twice by chlorine or fluorine,

R ^{8 stands} for hydrogen or for each optionally optionally substituted methyl, ethyl, n- or i-propyl, n- or i-butyl, the following preferably being considered as substituents:

Cyano, carboxyl, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfonyl, methylsulfonyl, ethylsulfylyl, methoxy Ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,

R ⁸ furthermore represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl which is optionally mono- or disubstituted by fluorine and / or chlorine,

R ⁸ furthermore represents cyclopropyl, cyclopentyl or cyclohexyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl, and

R ⁸ together with R ⁷ for butane-1,4-diyl, pentane-l, 5-diyl or

3-oxapentane-1,5-diyl. Compounds of formula (I), characterized in that

R ^{1 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine,

R ^{2 represents} hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine,

R ^{3 represents} fluorine or chlorine,

R ^{4 represents} chlorine or bromine,

R ^{5 represents} hydrogen or one of the radicals -R ⁷ , -OR ⁷ , -SR ⁷ , -NH-R ⁷ or -NR ⁷ R ⁸ ,

R ⁷ for each optionally mono- or disubstituted

Is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo-pentyl, the substituents in each case preferably in

Consider:

Cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, acetyloxymethyl, acetylmethoxy,

R ⁷ furthermore represents ethenyl, propenyl, ethynyl or propynyl which is optionally mono- or disubstituted by fluorine and / or chlorine or phenyl, R ⁷ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl or cyclohexylethyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl,

R ⁷ furthermore represents phenyl, benzyl, phenylethyl which are each substituted once, twice or three times, identically or differently,

Phenylpropyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, furyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl,

Oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrrolidinyl, piperidinyl, 1,3-benzodioxolylmethyl or chromanyl, the following being preferred in each case:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, methylthio, Ethylthio, methylsulfmyl, methylsulfonyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, 2-chlorophenyl, 2,6-dichlorophenyl,

R ^{8 represents} hydrogen or methyl or ethyl, n- or i-propyl, n- or i-butyl, which are each optionally monosubstituted, the following being preferred as substituents:

Cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy,

R ⁸ further represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl which is optionally mono- or disubstituted by fluorine and / or chlorine, and R ⁸ furthermore represents cyclopropyl, cyclopentyl or cyclohexyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl and / or ethyl.

4. Compounds of formula (I) according to claim 1, characterized in that

R ¹ for each methyl or optionally substituted by fluorine

Ethyl stands,

R represents hydrogen or methyl or ethyl optionally substituted by fluorine, and

R ⁵ each represents methyl, ethyl or n- or i-propyl which is optionally mono- or disubstituted by fluorine or chlorine,

for ethenyl or propenyl optionally substituted by fluorine and / or chlorine or phenyl,

for cyclopropyl, cyclopentyl or cyclohexyl, each optionally substituted once or twice, identically or differently, by fluorine, chlorine, methyl and / or ethyl, or

for each optionally by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, diflourmethyl, 2-chlorophenyl or

2,6-dichlorophenyl substituted benzyl, phenylethyl, furyl, thienyl, benzothienyl, oxazolyl, isoxazolyl or 1,3-benzodioxolylmethyl. Process for the preparation of compounds of the formula (I) according to one of Claims 1 to 4, characterized in that compounds of the formula (II)

in which

Q ¹ , QA RR ² . ³ _> R ⁴ and R ^{6 have} the meaning given in one of claims 1 to 4,

with halocarbonyl compounds of the general formula (III)

in which

R ^{5 has} the meaning given in one of claims 1 to 4 and

X represents halogen,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

6. Agent, characterized by a content of at least one compound of formula (I) according to one of claims 1 to 4 and conventional extenders and / or surface-active substances.

7. Use of compounds of formula (I) according to one of claims 1 to 4 for combating undesirable plants.

8. A method for controlling unwanted plants, characterized in that one or more compounds of the formula (I) according to any one of claims 1 to 4 on the undesired plants and / or their

Living space.