DE19918725A1 - New heterocyclic-substituted N-cyano-sulfonanilide compounds, useful as total or selective pre- or post-emergence herbicides, showing desiccant, defoliant, germination inhibiting and especially weed-killing activities - Google Patents

Abstract

N-Cyano-N-(3-heterocyclyl-phenyl)-sulfonamides (I) are new. N-Cyano-N-(3-heterocyclyl-phenyl)-sulfonamides of formula (I) are new. R1 = H, CN, halo; R2 = OH, CN, NO2, CSNH2, CONH2, halo, -R3, -Q1-R3 or -Q1-C(Q)2-R<3>; R3 = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl or heterocyclylalkyl (all optionally substituted); Z<1> = an optionally substituted heterocyclic group of one of 52 general formulae (mainly containing N; a few bonded via imino); and Q1, Q2 = O, S. Full definitions are given in the 'DEFINITIONS - Full Definitions' field. An Independent claim is included for the preparation of (I).

Description

The invention relates to new substituted N-cyano-sulfonic acid anilides, a process for their preparation and their use as herbicides.

It is already known that certain substituted sulfonic acid anilides are herbicidal Have properties (cf. EP 408382, EP 563384, EP 609734, EP 648749, US 4818275, US 4909831, WO 95/17391, WO 95/29158, WO 95/29168, WO 95/30661, WO 96/18618).

The properties of the previously known substituted sulfonic acid However, anilides do not meet the high standards in various aspects demands on modern plant treatment products.

There have now been new substituted N-cyano-sulfonic acid anilides of the general formula (I)

in which
R ^{1 represents} hydrogen, cyano or halogen,
R ^{2 represents} hydroxy, cyano, nitro, thiocarbamoyl, carbamoyl, halogen or one of the following groups -R ³ , -Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ ,
R ^{3 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and
Z represents one of the heterocyclic groupings below,

in which
Q ^{1 represents} O (oxygen) or S (sulfur),
Q ^{2 represents} O (oxygen) or S (sulfur),
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, cycloalkyl or Cyclo alkylalkyl stands, and
R ^{5 represents} hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where appropriate two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a grouping from the series - SO-, SO ₂ -, -NH- or -N (alkyl) - are interrupted alkanediyl or alkenediyl at the beginning (or at the end) or within the hydrocarbon chain,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or methylene and
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
where Y ¹ and Y ² are different in each individual case,
found.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl - also in connection with heteroatoms, such as in alkoxy - are in each case straight-chain or branched.
R ¹ preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R ² preferably represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or one of the following groups -R ³ , Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ .
R ³ preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each in each case optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, in each case optionally by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ - C ₄ haloalkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by cyano, Nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ - haloalkoxy substituted heterocyclyl or heterocyclylalkyl with each 2 to 6 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part.
Z preferably represents one of the heterocyclic groupings below

R ⁴ preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy having 1 to 6 carbon atoms, each optionally substituted by halogen Alkenyl or alkynyl each having 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen alkenyloxy or alkynyloxy each 3 to 6 carbon atoms, for alkylthio with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each optionally substituted by halogen alkenylthio or alkynylthio each with 3 to 6 carbon atoms, for alkylamino or dialkylamino each with 1 up to 6 carbon atoms in the alkyl groups, or for each given gene Is cycloalkyl or cycloalkylalkyl 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.
R ⁵ preferably represents hydrogen, hydroxyl, amino, cyano, for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, each optionally by halogen substituted alkenyl or alkynyl each having up to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl 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, or for phenyl or phenyl-C ₁ - each optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy C ₄ alkyl.

Two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together preferably represent optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the Series -SO-, SO ₂ -, -NH- or -N (C ₁ -C ₄ alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each with up to 5 carbon atoms.
Y ¹ preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C ₁ -C ₄ alkyl) or methylene.
Y ² preferably represents a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C ₁ -C ₄ alkyl).
Y ¹ and Y ² are different in each individual case.
Q ¹ preferably represents O (oxygen).
Q ² preferably represents O (oxygen).
R ¹ particularly preferably represents hydrogen, fluorine or chlorine.
R ² particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl.
R ³ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. Butyl, for each optionally substituted by fluorine, chlorine or bromine, propenyl, butenyl, ethynyl, propynyl or butinyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl , Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl, or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoro methoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, furylmethyl, thienylmethyl, oxolylylethyl, pyrolylylethyl , Pyridinylmethyl, pyrimidinylmethyl.
R ⁴ particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, and in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyl oxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine , Methoxy or ethoxy substituted methylthio, ethylthio, n- or i-propylthio, for propenylthio optionally substituted by fluorine, chlorine or bromine, butenylthio, propinylthio or butinylthio, for methylamino, Ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl.
R ⁵ particularly preferably represents hydrogen, hydroxy, amino, cyano, methyl, ethyl, n- or i-propyl, n-, i, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy -, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, each optionally with fluorine, chlorine or Bromine-substituted propenyl, butenyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy or trifluoromethoxy substituted phenyl , Benzyl or phenylethyl.

Two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together are particularly preferably optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or one Grouping from the series -SO-, SO ₂ -, -NH- or -N (methyl) - propane-1,3-diyl (trimethylene), butane-1, interrupted at the beginning (or at the end) or within the hydrocarbon chain, 4-diyl (tetramethylene), pentane-1,5-diyl (penta methylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl.
Y ¹ particularly preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or methylene.
Y ² particularly preferably represents a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (methyl).
R ¹ very particularly preferably represents fluorine.
R ² very particularly preferably represents cyano or chlorine.
R ³ very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine or chlorine.
R ⁴ very particularly preferably represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy methoxy, ethoxy, n- or i-propoxy, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for methylthio, ethylthio, n optionally substituted by fluorine or chlorine - or i-Propylthio, for methylamino, ethylamino, n- or i-propylamino or dimethylamino, or for cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl.
R ⁵ very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, meth- or ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or substituted by fluorine, chlorine, methoxy or ethoxy. or i-propylamino, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine or chlorine, for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, or for each optionally with nitro , Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluor methoxy substituted benzyl.

The individual radicals R ⁴ and R ⁵ - insofar as they are connected to the same heterocyclic grouping more than once, can have the same or different meanings in the context of the definitions given above as preferred, particularly preferred or very particularly preferred.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.  

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

According to the invention, particular preference is given to those compounds of the formula (I) in which a combination of those listed as particularly preferred above Meanings exist.

According to the invention, those compounds of the Formula (I), in which a combination of the above is particularly preferred added listed meanings is present.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

Examples of the compounds of the general formula (I) according to the invention are listed in the following groups.

Group 1

R ¹ , R ² and R ³ have the meanings given in the list below:

Group 2

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 3

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 4

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 5

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 6

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 7

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 8

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 9

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 10

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 11

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 12

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 13

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 14

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 15

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 16

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 17

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 18

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 19

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 20

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 21

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 22

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 23

R ¹ , R ² and R ³ have the meanings given above for group 1.

Group 24

R ¹ , R ² and R ³ have the meanings given above for group 1.

The new substituted N-cyano-sulfonic acid anilides of the general formula (I) have interesting biological properties. They stand out in particular characterized by strong and selective herbicidal activity.

The new substituted N-cyano-sulfonic acid anilides of the general formula (I) are obtained if substituted sulfonic acid anilides of the general formula (II)

in which
R ¹ , R ² , R ³ and Z have the meanings given above,
with cyanating agents, if appropriate in the presence of reaction auxiliaries and if appropriate in the presence of diluents.

If, for example, 5-chloro-4-methyl-2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -2,4-dihydro-3H-1,2,4-triazol-3-one and cyanogen bromide are used as Starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the substituted N-cyano sulfonic acid anilides 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 (II), R ¹ , R ² , R ³ and Z preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R ¹ , R ² , R ³ and Z have been given.

The starting materials of the general formula (II) are known and / or can be according to processes known per se (cf. EP 408 382, EP 563 384, EP 609 734, EP 648 749, US 4,818,275, US 4,909,831, WO 95/17391, WO 95/29158, WO 95/29168, WO 95/30661, WO 96/18618).

The inventive method for the production of substituted N-cyano-sul Fonsäureaniliden the general formula (I) is using Cyanie resources carried out. Suitable cyanating agents are, for example, cyano halogen compounds, such as. B. cyanogen bromide or cyanogen chloride, or sulfonic acid cyanides, such as B. benzenesulfonic acid cyanide or p-toluenesulfonic acid cyanide.

The cyanating agents required are known synthetic chemicals.  

As reaction aids for the process according to the invention generally come mean the usual inorganic or organic bases or acid acceptors in Consideration. These preferably include alkali metal or alkaline earth metal or acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as for example 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, -methanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; further also basic organic nitrogen compounds, such as trimethyl amine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N- Dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-Di methyl 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-diaza bicyclo [5,4,0] -undec-7-ene (DBU).

As a diluent for carrying out the method according to the invention inert organic solvents are particularly suitable. This includes ins special aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra chlorinated carbon; 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-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as acetic acid methyl ester or ethyl acetate, or sulfoxides such as dimethyl sulfoxide.  

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between -20 ° C and + 150 ° C, preferably between 10 ° C and 100 ° C.

The process according to the invention is generally carried out under normal pressure leads. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar to lead.

To carry out the process according to the invention, the starting materials in 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 were carried out a reaction auxiliary and the reaction mixture is in space agitated several hours at the required temperature. The on work is carried out according to customary methods (cf. games).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used. The active compounds according to the invention can, for. B. ver in the following plants be applied:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,  Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.  

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, 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 areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.

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 im impregnated natural and synthetic materials as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, ie emulsifiers and / or dispersants and / or foam generating means.  

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. 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 funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates as well as protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite leach and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.  

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (- sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, Butylates, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo methoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorine sulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra sulfuron (methyl), chlorosulam (methyl), cumyluron, cyanazine, cybutryne, Cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (- methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone,  Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet sulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, fluprop acil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (- meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiaz uron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxa diazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendi methalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primi sulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulf uron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (- methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl), quizalofop (-P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, sulfentrazone, sulfometuron (methyl), sulfosate, sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thia fluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarb azil, tralkoxydim, triallate, triasulftiron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin and triflusulfuron.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.  

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1

3.9 g (10 mmol) of 4- (4-chloro-2-fluoro-5-methylsulfonylaminophenyl) -1-methyl-2- difluoromethyl-1,2,4-triazolin-3,5-dione in 50 ml of tetrahydrofuran with 0.4 g (12 mmol) sodium hydride (75% in paraffin) and the mixture becomes 10 Minutes at 20 ° C stirred. Then 4.3 g (24 mmol) of p-toluenesulfonyl cyanide added and the reaction mixture is stirred at 20 ° C for 12 hours. The suspension is concentrated on a rotary evaporator, the residue with water stirred, extracted with dichloromethane, the organic phase with saturated sodium hydrogen carbonate solution and then washed with water, over sodium sulfate dried and concentrated on a rotary evaporator. For cleaning, the viscous Product stirred in diisopropyl ether, the precipitated solid is suction filtered and dried.

2.2 g (53% of theory) of 4- [5- (N-cyano-N-methylsulfonylamino) - are obtained. 4-chloro-2-fluoro-phenyl] -1-methyl-2-difluoromethyl-1,2,4-triazoline-3,5-dione from Melting point 80 ° C.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, for example the compounds of the general formula (I) listed in Table 1 below can also be prepared.

Table 1

Examples of the compounds of the formula (I)

Examples of use Example A Pre-emergence test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is sprayed with the active ingredient preparation so that the ge desired amount of active ingredient is applied per unit area. The concentration the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired amount of active ingredient is 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 annihilation.

In this test, for example, the compounds according to the preparation example show 1, 2 and 3 with good tolerance to crops, such as. B. Wheat and soy, very effective 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, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5-15 cm have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l 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 annihilation.

In this test, for example, the compounds according to the preparation example show 1, 2 and 3 with good tolerance to crops, such as. B. wheat, very strong action against weeds.

Claims (10)

1. Substituted N-cyano-sulfonic acid anilides of the general formula (I),
in which
R ^{1 represents} hydrogen, cyano or halogen,
R ^{2 represents} hydroxy, cyano, nitro, thiocarbamoyl, carbamoyl, halogen or one of the following groups -R ³ , -Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ ,
R ^{3 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and
Z represents one of the heterocyclic groupings below,
in which
Q ^{1 represents} O (oxygen) or S (sulfur),
Q ^{2 represents} O (oxygen) or S (sulfur),
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, di alkylamino, Cycloalkyl or cycloalkylalkyl,
R ^{5 represents} hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenyl alkyl,
where optionally two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO -, SO ₂ -, -NH- or -N (alkyl) - at the beginning (or at the end) or interrupted alkanediyl or alkenediyl within the hydrocarbon chain,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or methylene and
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
where Y ¹ and Y ² are different in each individual case. 2. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, cyano, fluorine, chlorine or bromine,
R ^{2 represents} hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or one of the following groups -R ³ , Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ ,
R ³ for alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy having 1 to 6 carbon atoms, for each optionally substituted by halogen, alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cyclo alkyl group and optionally 1 to 4 carbon atoms in the alkyl, for each optionally by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by Cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted heterocyclyl or heterocyclylalkyl, each with 2 to 6 Koh lenstoffatomen and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen atoms in the heterocyclic group and optionally 1 to 4 carbon atoms in the alkyl part,
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each alkenyl optionally substituted by halogen or Alkynyl each having 2 to 6 carbon atoms, for alkoxy or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, for each alkenyloxy or alkynyloxy optionally substituted by halogen, each having 3 to 6 carbon atoms, for alkylthio optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy having 1 to 6 carbon atoms, for each optionally substituted by halogen, alkenylthio or alkynylthio each having 3 to 6 carbon atoms, for alkylamino or dialkyl amino each 1 to 6 carbon atoms in the alkyl groups, or for each optionally by cyano , Halogen or C ₁ -C ₄ alkyl-substituted cycloalkyl 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 ⁵ for hydrogen, hydroxy, amino, cyano, for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, for alkenyl optionally substituted by halogen or Alkynyl each having up to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl 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, or for each phenyl or phenyl-C ₁ -C ₄ optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy alkyl stands, whereby
two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - for optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO- , SO ₂ -, -NH- or -N (C ₁ -C ₄ alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each having up to 5 carbon atoms,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C ₁ -C ₄ alkyl) or methylene and
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C ₁ -C ₄ alkyl), where
Y ¹ and Y ² are different in each individual case. 3. Compounds according to claim 1 or 2, characterized in that
R ^{1 represents} hydrogen, cyano, fluorine or chlorine,
R ^{2 represents} cyano, thiocarbamoyl, chlorine or trifluoromethyl,
R ³ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butyl, for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, Cyclopentylmethyl or cyclohexylmethyl, each optionally with cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl, or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted heterocyclyl or heterocyclylalkyl from the series comprising furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, furylmethyl, thienylmethyl, pyrrolylmethyl, pyrazolylmethyl, oxazolylmethyl, isoxazolylmethyl, thiazolylmethyl, pyridinylmethyl, pyrimidinyl methyl group,
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n -, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for methoxy optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, for propenyloxy, butenyloxy, propynyloxy or butinyloxy, each optionally substituted by fluorine, chlorine or bromine, for each optionally substituted by cyano, fluorine, chlorine, Methoxy or ethoxy substituted methylthio, ethyl thio, n- or i-propylthio, for propenylthio, butenylthio, propynylthio or butinylthio, each optionally substituted by fluorine, chlorine or bromine, for methylamino, ethylamino, n- or i- Propyl amino, dimethylamino or diethylamino, or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,
R ⁵ for hydrogen, hydroxy, amino, cyano, for each methyl, ethyl, n- or i-propyl, n-, i-, optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, each optionally with fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclo hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, cyano , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy or trifluoromethoxy substituted phenyl , Benzyl or phenylethyl, and
two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - for optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or a grouping from the series SO-, SO ₂ -, -NH- or -N (methyl) - Propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) interrupted at the beginning (or at the end) or within the hydrocarbon chain ), Pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or methylene,
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (methyl), where
Y ¹ and Y ² are different in each individual case. 4. Compounds according to claim 1 to 3, characterized in that
R ^{1 represents} fluorine,
R ^{2 represents} cyano or chlorine and
R ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine or chlorine. 5. Compounds according to one of claims 1 to 4, characterized in that
Z represents one of the heterocyclic groupings below
6. Compounds according to one of claims 1 to 5, characterized in that
Q ^{1 stands} for O (oxygen) and
Q ^{2 stands} for O (oxygen). 7. Compounds according to one of claims 1 to 6, characterized in that
R ⁴ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by cyano, Fluorine, chlorine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, for methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for each methyl thio, ethylthio, n- or i-propylthio optionally substituted by fluorine or chlorine , stands for methylamino, ethylamino, n- or i-propylamino or dimethylamino, or for cyclopropyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, and
R ^{5 represents} hydrogen, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyl, butenyl, propynyl or butynyl which are optionally substituted by fluorine or chlorine, for each cyclo propyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, or for each optionally by nitro, cyano, Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted benzyl. 8. A process for the preparation of compounds according to any one of claims 1 to 7, characterized in that substituted sulfonic acid anilides of the general formula (II)
in which
R ¹ , R ² , R ³ and Z have the meaning given in one of claims 1 to 7,
with cyanating agents, if appropriate in the presence of reaction auxiliaries and if appropriate in the presence of diluents. 9. Herbicidal agents, characterized by the content of at least one compound dung according to one of claims 1 to 7 and conventional extenders. 10. Use of at least one compound according to one of the claims 1 to 7 to control unwanted plants.