WO1994018177A1

WO1994018177A1 - Arylaminosulphonyl ureas

Info

Publication number: WO1994018177A1
Application number: PCT/EP1994/000138
Authority: WO
Inventors: Hans-Jochem Riebel; Hans-Joachim Santel; Markus Dollinger
Original assignee: Bayer Aktiengesellschaft
Priority date: 1993-02-01
Filing date: 1994-01-20
Publication date: 1994-08-18
Also published as: DE4302701A1; AU5969294A

Abstract

The invention relates to novel arylaminosulphonyl ureas of the general formula (I) in which R1 is possibly substituted alkyl with 2 to 10 carbon atoms, aryl or aralkyl, R2 is hydrogen, hydroxy, cyano, alkoxycarbonyl or possibly substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, aralkyloxy, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkylsulphonyl or arylsulphonyl, R3 is hydrogen or possibly substituted alkyl, alkenyl, alkinyl or aralkyl, X is hydrogen, halogen, cycloalkyl or possibly substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, Y is hydrogen, halogen or possibly substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, and Z is nitrogen or the C-R4 group, in which R4 is hydrogen, halogen, alkyl or alkoxy, and salts of compounds of the formula (I), and also processes for producing the novel compounds and their uses as herbicides.

Description

Arylaminosulfonylureas

The invention relates to new arylaminosulfonylureas, processes for their preparation and their use as herbicides.

It is already known that certain aminosulfonylureas, e.g. N- (4-methoxy-6-methyl-s-triazin-2-yl) -N '- (2-methyltMophenylaminosulfonyl) urea and N- (4,6-dimethyl-pyrimidm-2-yl) -N '- (2-methylthio-phenyl_unmosulfonyl) -haπιstoflF, have herbicidal properties (see. DE-OS 3243533).

However, these connections have not gained any significant importance.

The new arylaminosulfonylureas of the general formula (I)

in which

R 1 represents in each case optionally substituted alkyl having 2 to 10 carbon atoms, aryl or aralkyl,

R2 represents hydrogen, hydroxy, cyano, alkoxycarbonyl or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, aralkyloxy, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl,

R ^* - ^{* stands} for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl, X represents hydrogen, halogen, cycloalkyl or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,

Y represents hydrogen, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino and

Z represents nitrogen or the grouping C-R ^, wherein

R4 represents hydrogen, halogen, alkyl or alkoxy,

as well as salts of compounds of formula (I) found.

The new arylaminosulfonylureas of the general formula (I) are obtained if aminoazines of the general formula (II)

in which

R ^* - ^* , X, Y and Z have the meaning given above,

with chlorosulfonyl isocyanate, if appropriate in the presence of a diluent, and the chlorosulfonylureas of the general formula (III) formed in this process

in which

R ^*** , X, Y and Z have the meaning given above,

with arylamines of the general formula (IV)

in which

Rl and R2 have the meaning given above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and if appropriate converting the compounds of the formula (I) thus obtained into salts by customary methods.

Another possible production method for the compounds of the formula (I) according to the invention is outlined below, where R--, R- ^* R * - ^* , X, Y and Z have the meaning given above and R ^ for alkyl (in particular methyl or ethyl), aralkyl (in particular benzyl) or aryl (in particular phenyl):

(IV) (V)

The new arylaminosulfonylureas of the general formula (I) are notable for strong herbicidal activity. Surprisingly, the new compounds of the formula (I) have a considerably stronger herbicidal action than the structurally similar known compound N- (4-methoxy-6-methyl-s-triazin-2-yl) -N '- (2-methylthio- phenylaminosulfonyl) urea.

The invention preferably relates to compounds of the formula (I) in which

Rl for C2-C6-alkyl optionally substituted by halogen or for in each case optionally by halogen, C1-C4-alkyl, Cj-C ^ haloalkyl, C1-C4-alkoxy, C _] -C4-haloalkoxy, Cι -C4 Alkoxycarbonyl, cyano or nitro substituted phenyl or benzyl,

R2 for hydrogen, hydroxy, cyano, Ci-Cg-alkoxy-carbonyl, for Cj-Cö-alkyl optionally substituted by halogen, cyano, carboxy, C ^* (-C4-alkylcarbonyl or Cj-C4-alkoxycarbonyl, for each optionally substituted by halogen C3-Cg-alkenyl or C3-C6-alkynyl, for Cj-Cö-alkoxy or C3-Cg-alkenyloxy, for optionally by halogen, C1-C4-alkyl, Cj-C4-haloalkyl, Cι -C4 ~ alkoxy, Cj-C4-haloalkoxy, C ^* --C4-alkoxy-carbonyl, cyano or nitro substituted benzyloxy, for each Ci-Cg-alkylcarbonyl, C3-C6-cycloalkyl optionally substituted by halogen -carbonyl or phenylcarbonyl, or represents in each case optionally substituted by halogen C _] - Cö-alkylsulfonyl or phenylsulfonyl,

^~ R? for hydrogen, for C 1 -C 4 -alkyl optionally substituted by halogen, cyano, carboxy, C 1 -C 4 -alkyl carbonyl or C 1 -C 4 -alkoxy carbonyl, for C3-Cö-alkenyl optionally substituted by halogen or C3-C6-alkinyl, or represents optionally halogen-, C 1 -C 4 alkyl, C _j-C4 halo- genalkyl, C1-C4 alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkoxy-carbonyl, Cy ¬ ano or nitro substituted benzyl,

X for hydrogen, halogen, cyclopropyl, for C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C] -C 4 -alkylamino, each optionally substituted by halo or C 1 -C 4 -alkoxy, or represents di (C 3 -C 3 -alkyl) amino, Y for hydrogen, halogen, for C-1-C4-alkyl optionally substituted by halogen or C _] - C4-alkoxy, C ^* ! -C4-alkoxy, C \ -C4- alkylthio, C _] - C4- alkylamino, or for di- (C ^* ι-C3-alkyl) -amino, and

Z represents nitrogen or the grouping CR ⁴ , wherein

R ^{4 represents} hydrogen, halogen, C 1 -C 4 alkyl or C -C 4 alkoxy.

The invention further preferably sodium, potassium, magnesium, calcium, ammonium, -C-C4-alkyl-ammonium, di- (C] -C4-all_yl) -ammonium-, tri- (Cι -C4 -alkyl) -ammonium, C5- or Cö-cycloalkyl-ammonium and di- (C ^* --C2-alkyl) -benzyl-ammonium salts of compounds of formula (I), in which n, R--, R2_R ^* - ^* , X, Y and Z have the meanings preferably given above.

The invention relates in particular to compounds of the formula (I) in which

Rl represents ethyl, n- or i-propyl, n-, i- or s-butyl or phenyl,

R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,

R ^ represents hydrogen, methyl or ethyl,

X represents hydrogen, fluorine, chlorine, bromine, cyclopropyl, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,

Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, and

Z represents nitrogen or the grouping CR ⁴ , wherein

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, methyl or methoxy.

The general or preferred 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. This re- Standard definitions can be combined with one another, that is to say also between the specified preferred ranges.

The hydrocarbon radicals mentioned in the radical definitions, such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are straight-chain or branched, even if this is not expressly stated.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

If, for example, 4-chloro-6-methoxy-2-aminopyrimidine, chlorosulfonyl isocyanate and 2-ethyl-aniline are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

The aminoazines of the formula (II) to be used as starting materials in the process according to the invention are known synthetic chemicals, some of which are commercially available.

The arylamines of the formula (IV) which are also required as starting materials are also known and / or can be prepared by processes known per se (cf. DE-OS 3528033).

The process according to the invention for the preparation of the new arylaminosulfonylureas of the formula (I) is preferably carried out using diluents. Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl - And dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, and nitriles such as, for example Acetonitrile and propionitrile, amides such as e.g. Dimethylformamide, dimethyl acetamide and N-methylpyrrolidone as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

Acid acceptors which can be used in the process according to the invention are all acid binders which can customarily be used for such reactions. Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g. Calcium hydroxide, alkali carbonates and alcohols such as sodium and potassium carbonate, such as sodium and potassium tert-butoxide, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo [4,3,0] - non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2 , 2] octane (DABCO).

The reaction temperatures can be varied within a wide range in the process according to the invention. Generally one works at temperatures between -30 ° C and + 80 ° C, preferably at temperatures between -10 ° C and + 60 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.

To carry out the process according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).

If appropriate, salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then be isolated by evaporation or suction, if appropriate after prolonged stirring.

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow 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: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthi- um, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolaxacumumulus.

Dicotyledon 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, Sor¬ ghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittirpum, Eleocharis, Pas , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

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 compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. The compounds 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 and can be used for selective weed control in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon crops, especially in the post-emergence process.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, and soluble Before powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie 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.

The following are suitable as solid carriers:

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 and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfate leaching and methyl cellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue 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 of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids such as dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chloropropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propa-chlorine; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas, such as, for example, amidosulfuron, bensulfüron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfüron, metsulfüron-methyl, nicosulfüron, primisulfüron, pyrazosulfüron-ethyl, thifensulfüron-methyl, triasulfüron and tribenuron-methyl; Thiol carbamates, such as butylates, cyc- loate, dialallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate; Triazines, such as, for example, atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others, such as, for example, aminotriazole, benfüresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofümesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. 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 applied can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.

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

Preparation Examples:

example 1

7.7 g (50 mmol) of 2-amino-4,6-dimethoxy-pyrimidine are added at -5 ° C. with stirring to a mixture of 7.3 g (52 mmol) of chlorosulfonyl isocyanate and 100 ml of methylene chloride and the mixture is stirred at 0 ° C for 30 minutes.

Then 7.7 g (50 mmol) of 2-ethylthio-aniline, 5.5 g (55 mmol) of triethylamine and 50 ml of methylene chloride are added and the reaction mixture is stirred at 20 ° C. for 15 hours.

Then it is washed with water and with 10% hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is crystallized by digesting with ethanol and the product is isolated by suction.

16.3 g (79% of theory) of N- (4,6-dimethoxy-pyrimidin-2-yl) -N- (2-ethylthio-phenylaminosulfonyl) urea of melting point 126 ° C. are obtained.

Analogously to Example 1 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 formula (I) listed in Table 1 below.

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

Example - R1 R2 R3 X Z Schmelz¬

No. point (° C)

2 CH ₅ HH CH ₃ OCH ₃ CH (amorphous)

3 C ₂ H ₅ HH OCH3 OCH3 N 1 ₂ 9

4 C ₂ H ₅ HH CH ₃ OCH3 N 130

5 C ₂ H ₅ H CH3 CH ₃ OCH3 N 68

6 C ₂ H ₅ H CH ₃ OCH3 OCH3 N 88

7 C ₂ H ₅ CH (CH ₃ ) ₂ H OCH3 OCH3 CH 157

8 C ₂ H ₅ CH (CH ₃ ) ₂ H OCH3 OCH3 N 175

9 CH ₅ CH (CH ₃ ) ₂ H CH ₃ OCH3 N 179

10 n-C3Hγ H H OCH3 OCH3 CH 136

11 n-C3H H H OCH3 OCH3 N 1 16

12 nC ₃ H ₇ HH • CH ₃ OCH3 N 1 ₂₂ Table 1 (continued)

Example - Rl R2 R3 X Y Schmelz¬

No. point (° C)

13 CH (CH ₃ ) ₂ HH OCH ₃ OCH3 CH 145

14 CH (CH ₃ ) ₂ HH OCH3 OCH3 N 130

15 CH (CH ₃ ) ₂ HH CH ₃ OCH3 N (amorphous)

16 C ₆ H ₅ HH OCH3 OCH3 CH 141

17 C ₆ H ₅ HH OCH3 OCH3 N 148

18 C ₆ H ₅ HH CH ₃ OCH3 N 105

19 C ₂ H ₅ HH Cl OCH3 CH 160

Examples of use:

In the application examples, the following compound (A) is used as a reference substance:

N- (4-methoxy-6-methyl-s-triazin-2-yl) -N '- (2-methylthio-phenylaminosulfonyl) urea substance (known from DE-OS 3243533).

Example A

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 concentration.

Test plants which have 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 the particular amounts of active compound desired are applied in 2000 l of water / ha. After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

It means:

O% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compound according to Preparation Example 1 shows a clear superiority in effectiveness compared to the prior art.

Table A: Post emergence test (greenhouse)

Active ingredient effort- wheat abuti- galium ipomoea poly- viola amount (g / ha) ion gonum

(A) (known) 500 80 80 30

(1) 125 95 90 90 70 70

Claims

1. Arylaminosulfonylureas of the general formula (I)

in which

R 1 stands for optionally substituted alkyl with 2 to 10 carbon atoms, aryl or aralkyl,

R3 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl or aralkyl,

X represents hydrogen, halogen, cycloalkyl or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,

Y stands for hydrogen, halogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino and

Z represents nitrogen or the grouping CR ⁴ , wherein

R ^{4 represents} hydrogen, halogen, alkyl or alkoxy,

and salts of compounds of formula (I).

2. Arylaminosulfonylureas of formula (I) according to claim 1, characterized ge indicates that therein Rl for C2-C6-alkyl which is optionally substituted by halogen or for in each case optionally by halogen, -C-C4-alkyl, C] -C4-haloalkyl, C1-C4-alkoxy, Cι-C4-halogen-alkoxy, -C-C4-alkoxy carbonyl, cyano or nitro substituted phenyl or benzyl,

R ² for hydrogen, hydroxy, cyano, Ci-Cg-alkoxy-carbonyl, for Cf -Cg-alkyl which is optionally substituted by halogen, cyano, carboxy, Cj-C4-alkyl-carbonyl or C \ - C4-alkoxy-carbonyl , for each optionally substituted by halogen C3-Cö-alkenyl or C3-Cg-alkynyl, for CJ-CÖ-alkoxy or C3-C6-alkenyloxy, for optionally by halogen, Cj ^ -alkyl, ^^ - haloalkyl, Cι -C -alkoxy, C! -C - haloalkoxy, Cj-C4-alkoxy-carbonyl, cyano or nitro substituted benzyloxy, for in each case optionally substituted by halogen C ^ - Cg-alkylcarbonyl, C3-C6-cycloalkyl-carbonyl or phenylcarbonyl , or represents in each case optionally substituted by halogen Cj-Cg-alkylsulfonyl or phenylsulfonyl,

R3 for hydrogen, for optionally substituted by halogen, cyano, carboxy, C _j - C4-alkyl-carbonyl or C - [- C4-alkoxy-carbonyl-Ci-Cg-alkyl, for each optionally substituted by halogen C3-C6-alkenyl or C3-C6-alkynyl, or for benzyl optionally substituted by halogen, C \ - C4-alkyl, C ^* (-C4-haloalkyl, Cj- ^ alkoxy, Cj ^ -haloalkoxy, Cι-C4-alkoxycarbonyl, cyano or nitro stands,

X for hydrogen, halogen, cyclopropyl, for C ^* --C4-alkyl, Cι-C4 ~ alkoxy, C1-C4-alkylthio, C1-C4-alkylamino, optionally substituted by halogen or Cj-C4-alkoxy, or for di- (-C-C3-alkyl) -amino,

Y for hydrogen, halogen, in each case optionally substituted by halogen or C1-C4-alkoxy-CjCj-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, -C-C4-alkylamino, or for di- (-C-C3-alkyl) ) -amino stands, and

Z represents nitrogen or the grouping CR ⁴ , wherein R ^{4 represents} hydrogen, halogen, C i -C4-alkyl or C \ -C4-alkoxy,

and salts of these compounds.

3. arylaminosulfonylureas of the formula (I) according to claim 1, characterized in that therein

Rl represents ethyl, n- or i-propyl, n-, i- or s-butyl or phenyl,

R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,

R3 represents hydrogen, methyl or ethyl,

Z represents nitrogen or the grouping CR ⁴ , wherein

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, methyl or methoxy,

and salts of these compounds.

4. A process for the preparation of the arylaminosulfonylureas of the formula (I) according to claim 1, characterized in that aminoazines of the general formula (II)

in which R3, X, Y and Z have the meaning given in claim 1,

with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas of the general formula (III) formed

in which

R3, X, Y and Z have the meaning given above,

with arylamines of the general formula (IV)

in which

R- * and R ^{2 have} the meaning given in claim 1,

Herbicidal agents, characterized in that they contain at least one compound of the formula (I) according to Claim 1.

Use of compounds of the general formula (I) according to Claim 1 for combating undesired plant growth. 7. A method of combating weeds, characterized in that compounds of the general formula (I) according to Claim 1 are allowed to act on the weeds or their habitat.

8. A process for the preparation of herbicidal compositions, characterized in that compounds of the general formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents.