DE4435470A1 - Substituted phenylaminosulfonylureas - Google Patents

Abstract

The invention relates to novel substituted phenylaminosulphonyl ureas of the formula (I) in which A may be N or CH, Q may be O or S, R<1> and R<2> are mutually independently e.g. C1-C4 alkyl or C1-C4 alkoxy, R<3> may be H, halogen, C1-C4 alkyl or C1-C4 alkoxy, R<4> and R<5> may be individually C1-C6 alkyl or together C2-C5 alkanediyl, and R<6> may be C1-C6 alkyl, and salts of compounds of formula (I), a process for producing the novel compounds and their use as herbicides.

Description

The invention relates to new substituted phenylaminosulfonylureas, a Ver drive to their manufacture and their use as herbicides.

It is already known that certain substituted phenylaminosulfonylureas, such as B. the compounds 1- [2- (1,1-dimethoxy-ethyl) -phenylsulfamoyl] -3- (4- methyl-6-methoxy-1,3,5-triazin-2-yl) urea and 1- [2- (1,3-dioxolan-2-yl-me thyl) -phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea, herbic exhibit both properties (cf. EP-A 184122). Have these connections however, has no significant significance.

The new substituted phenylaminosulfonylureas of the gen my formula (I),

in which
A represents nitrogen, CH or C-halogen,
Q represents oxygen, sulfur, SO or SO₂,
R¹ represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each optionally substituted by halogen or C₁-C₄alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups,
R² stands for halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino or dialkylamino, each optionally substituted by halogen or C₁-C₄alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups,
R³ represents hydrogen-halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl, each optionally substituted by halogen or C₁-C₄alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups,
R⁴ individually represents alkyl with 1 to 6 carbon atoms optionally substituted by halogen or C₁-C₄alkoxy,
R⁵ individually represents alkyl with 1 to 6 carbon atoms optionally substituted by halogen or C₁-C₄alkoxy, or
together with R⁴ represents alkanediyl having 2 to 5 carbon atoms, and
R⁶ represents hydrogen or alkyl optionally substituted by halogen, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl having 1 to 6 carbon atoms,
as well as salts of compounds of formula (I), where the compounds 1- [2- (1,1-dimethoxy-ethyl) -phenylsulfamoyl] -3- (4-methyl-6-methoxy-1, -3.5- triazin-2-yl) urea and 1- [2- (1,3-dioxolan-2-ylmethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazine 2-yl) urea (both known from EP-A 184122) are excluded by disclaimers.

The new substituted phenylaminosulfonylureas of the general are obtained Formula (I) if aminoazines of the general formula (II)

in which
A, R¹ and R² have the meaning given above,
with chlorosulfonyl isocyanate, if appropriate in the presence of a diluent, and the chlorosulfonylureas formed in this process of the general
Formula (III)

in which
A, R¹ and R² have the meaning given above,
with substituted anilines of the general formula (IV)

in which
Q, R³, R⁴, R⁵ and R⁶ have the meaning given above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and optionally convert the compounds of the formula (I) thus obtained into salts by customary methods.

The new substituted phenylaminosulfonylureas of the general formula (I) are characterized by strong and selective herbicidal activity.

The invention preferably relates to compounds of the formula (I) in which
A represents nitrogen, CH or C-halogen,
Q represents oxygen, sulfur, SO or SO₂,
R¹ represents hydrogen-fluorine, chlorine, bromine or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 3 carbon atoms in the individual alkyl groups, optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R² stands for fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkyl sulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups,
R³ represents hydrogen, fluorine, chlorine, bromine, or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups,
R⁴ individually represents alkyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy and has 1 to 4 carbon atoms,
R⁵ individually represents alkyl optionally substituted by fluorine, chlorine, methoxy or ethoxy and has 1 to 4 carbon atoms, or
together with R⁴ represents alkanediyl having 2 to 4 carbon atoms, and
R⁶ represents hydrogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by fluorine, chlorine, C₁-C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulfinyl or C₁-C₃-alkylsulfonyl,
where the compounds 1- [2- (1,1-dimethoxyethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea and 1- [ 2- (1,3-Dioxolan-2-yl-methyl) -phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) -h-urea (both known from EP-A 184122) are excluded by disclaimers.

The invention further preferably relates to sodium, potassium, Magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di- (C₁-C₄-alkyl) - ammonium-, tri- (C₁-C₄-alkyl) -ammonium-, C₅- or C₆-cycloalkyl-ammonium- and di- (C₁-C₂-alkyl) -benzyl-ammonium salts of compounds of the formula (I), in which A, Q, R¹, R², R³, R⁴, R⁵ and R⁶ the above preferably indicated Have meaning.

The invention relates in particular to compounds of the formula (I) in which
A represents nitrogen or CH,
Q represents oxygen or sulfur,
R¹ represents hydrogen, chlorine or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R² stands for chlorine or for methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R³ stands for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁴ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁵ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or
together with R⁴ stands for ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene), and
R⁶ represents hydrogen or represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
where the compounds 1- [2- (1,1-dimethoxyethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea and 1- [ 2- (1,3-Dioxolan-2-yl-methyl) -phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) -h-urea (both known from EP-A 184122) are excluded by disclaimers.

The connections of the following general are particularly emphasized my formula (Ia), in which Q, R¹, R², R³, R⁴, R⁵ and R⁶ the above as ins have particularly preferred meaning.

The radicals listed above or specified in preferred ranges definitions apply to both the end products of the formula (I) and ent speaking for the respective starting materials or Intermediates. These residual definitions can be among each other, so also between the specified ranges of preferred connections, any com be binated.  

For example, 2-amino-4-chloro-6-methoxy-pyrimidine, chlorine is used sulfonyl isocyanate and 2- (1,1-dimethoxy-ethyl) aniline as starting materials, so can the course of the reaction in the process of the present invention is as follows Formula scheme are outlined:

The process according to the invention for the preparation of the compounds of all general formula (I) to use as starting materials aminoazines are by the formula (II) is generally defined. In formula (II), A, R¹ and R² have before preferably or in particular those meanings already mentioned above in Zu in connection with the description of the compounds of formula (I) as preferred or as particularly preferred for A, R¹ and R².

The starting materials of the formula (II) are known synthetic chemicals.

To continue to be used as starting materials in the process according to the invention The substituted anilines are generally defined by the formula (IV). In the Formula (IV) have Q, R³, R⁴, R⁵ and R⁶ preferably or in particular the those meanings that are already above in connection with the description of the compounds of formula (I) as preferred or as particularly preferred for Q, R³, R⁴, R⁵ and R⁶ were specified.

The starting materials of formula (IV) are also known and / or can be known processes can be prepared (cf. EP-A 184122; US-P  4592776; Synthesis 1983, 203-205; Liebigs Ann. Chem. 1979, 1130-1136; Forth position examples).

The inventive method for producing the new compounds of Formula (I) is preferably carried out using diluents guided. Practically all inert organic come as diluents Solvent in question. 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 iso propyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl esters, nitriles such as B. acetonitrile and propionitrile, amides such as. B. Dimethyl form amide, dimethylacetamide and N-methylpyrrolidone and dimethyl sulfoxide, tetra methylene sulfone and hexamethylphosphoric triamide.

All of the customary acid acceptors can be used in the process according to the invention used for such reactions usable acid binders will. Alkali metal hydroxides such as e.g. B. sodium and Potassium hydroxide, alkaline earth metal hydroxides such. B. calcium hydroxide, alkali metal carbonates and alcoholates such as sodium and potassium carbonate, such as sodium and Potassium tert-butoxide, furthermore 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-diazabicydo [2,2,2] octane (DABCO).

The reaction temperatures can in the process according to the invention in can be varied over a wide range. Generally one works at Tem 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 guided. However, it is also possible to increase or decrease pressure work.  

They are required to carry out the method according to the invention th raw materials generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case to use a larger excess. The reactions are general in a suitable diluent in the presence of an acid acceptor performed, and the reaction mixture is required for several hours at each stirred temperature. Working up takes place in the inventive Processes in each case according to customary methods (cf. the production examples).

From the compounds of general formula (I) according to the invention, ge if necessary salts are produced. Such salts are obtained in a simple manner by conventional salt formation methods, for example by dissolving or dispersing yaw a compound of formula (I) in a suitable solvent, such as e.g. B. methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition a suitable base. The salts can then - if necessary after a long time Stirring - be isolated by concentration or suction.

The active compounds according to the invention can, for. B. in the following plants be used:

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.

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

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

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and Places with and without tree cover. Likewise, the connections to Weed control in permanent crops, e.g. B. forest, ornamental trees, fruit, wine, Citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hops, on ornamental and sports turf and pastures and for selective Weed control can be used in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for selective control of dicotyledon weeds in monocotyledons and dicotyledons Cultures, both pre-emergence and post-emergence.

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as fine encapsulation in poly other fabrics.

These formulations are prepared in a known manner, e.g. B. by Vermi 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 carbons Hydrogen, 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 cyclo hexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
e.g. B. 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: 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 agents come into question: z. B. nonionic 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 and protein hydrolyzates; as dispergents are: B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine 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 Weight percent active ingredient, preferably between 0.5 and 90%.

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

Known herbicides are suitable for the mixtures, for example anilides, such as B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy alkanoic acid esters, such as. B. diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, Haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as e.g. B. Alachlor, Acetochlor, Butachlor, Metaza chlorine, metolachlor, pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, Fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, like e.g. B. chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenz thiazuron; Hydroxylamines, such as. B. alloxydim, clethodim, cycloxydim, Sethoxydim and tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazametha benz, imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlobenil and Ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as. B. Amido sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, Metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifene sulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. Butylates, Cycloates, Diallates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thioben carb and triallates; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Ter butryne and terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and Metribuzin; other, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and tridiphanes.  

Also a mixture with other known active ingredients, such as fungicides, insecticides, Acaricides, nematicides, bird repellants, plant nutrients substances 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 will. 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 can be applied. You can also sow before sowing Be incorporated into the floor.

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 10 g and 10 kg of active ingredient per hectare of soil area, preferably between 50 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

0.6 g (3.8 mmol) of 2-amino-4,6-dimethoxy-pyrimidine become a with stirring solution of 0.5 g (3.5 mmol) of chlorosulfonyl isocyanate in 10 cooled to 0 ° C. ml of methylene chloride are added and the mixture is stirred at 20 ° C. for 30 minutes. Then 0.73 g (3.5 mmol) of 2-methyl-2- (2-amino-3-ethylphenyl) -1,3-dioxolane and 0.53 g (5.25 mmol) triethylamine - each in approx. 10 ml methylene chloride dissolved - added and the reaction mixture is 15 hours at 20 ° C. touched. Then with 1N sodium dihydrogen phosphate solution and still washed twice with water, dried with sodium sulfate and filtered. The The filtrate is concentrated in a water jet vacuum and the residue is digested with ethanol and the crystalline product isolated by suction.

0.7 g (43% of theory) of N- (4,6-dimethoxy-pyrimidin-2-yl) -N ′ - [2- (2- methyl-1,3-dioxolan-2-yl) -6-ethylphenylaminosulfonyl] urea from the enamel point 165 ° C.

Example 2

0.51 g (3.3 mmol) of 2-amino-4,6-dimethoxy-pyrimidine are added with stirring a cooled to 0 ° C solution of 0.43 g (3 mmol) of chlorosulfonyl isocyanate in  10 ml of methylene chloride and the mixture is 30 minutes at 20 ° C. touched. Then 0.8 g (3 mmol) of 2-ethyl-2- (2-amino-3-ethylphenyl) -1,3- dithian and 0.45 g (4.5 mmol) triethylamine - each in approx. 10 ml methylene chloride dissolved - added and the reaction mixture is at 15 hours Stirred at 20 ° C. Then with 1N sodium dihydrogen phosphate solution and washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue digested with petroleum ether and the crystalline product isolated by suction.

0.9 g (57% of theory) of N- (4,6-dimethoxypyrimidin-2-yl) -N ′ - [2- (2- ethyl-1,3-dithian-2-yl) -6-ethylphenylaminosulfonyl] urea, melting point 179 ° C.

Analogous to Examples 1 and 2 and in accordance with the general Description of the manufacturing method according to the invention can for example also the compounds listed in Table 1 below Formula (I) can be prepared.

Starting materials of formula (IV) Example (IV-1)

2.3 g (14 mmol) of 2-acetyl-6-ethyl-aniline are dissolved in 40 ml of ethylene glycol and 4.1 g (37 mmol) of chloro-trimethylsilane are added dropwise at 20 ° C. with stirring. The mixture is stirred at 20 ° C. for 20 hours, then diluted with diethyl ether, washed twice with saturated sodium hydrogen carbonate solution, with Dried sodium sulfate and filtered. The filtrate is concentrated and the Residue by column chromatography (hexane / ethyl acetate, vol .: 9: 1, Silica gel) cleaned.

1.1 g (38% of theory) of 2-methyl-2- (2-amino-3-ethylphenyl) -1,3-di are obtained oxolan as an amorphous product.

Example (IV-2)

3.0 g (17 mmol) of 2-ethyl-6-propionyl-aniline are dissolved in 30 ml of methylene chloride dissolved and at 20 ° C 5.5 g (51 mmol) of propane-1,3-dithiol and 9.6 g (68 mmol) of boron trifluoride etherate was added. The mixture is at 20 hours Stirred at 20 ° C, then diluted with diethyl ether and with 10% sodium hydroxide Solution stirred. The organic phase is then washed with water, with  Dried sodium sulfate and filtered. The filtrate is concentrated and the The residue was purified by column chromatography (methylene chloride / silica gel). 2.0 g (44% of theory) of 2-ethyl-2- (2-amino-3-ethylphenyl) -1,3-dithiane are obtained as an amorphous product.  

Examples of use 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, mix 1 Part by weight of active ingredient with the specified amount of solvent indicates that given amount of emulsifier and dilute the concentrate with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation 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 2000 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, shows the connection according to Production Example 3 with very good tolerance to crops, such as. B. wheat, strong Effect against weeds.  

Example B 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, 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 desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours the soil is poured with the active ingredient preparation. You keep the what amount of water per unit area expediently constant. The active ingredient con Concentration in the preparation does not matter, only the opening is decisive amount of active ingredient per unit area. 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, shows the connection according to Production Example 3 with very good tolerance to crops, such as. B. cotton, star ke effect against weeds.

Claims (9)

1. Substituted phenylaminosulfonylureas of the general formula (I), in which
A represents nitrogen, CH or C-halogen,
Q represents oxygen, sulfur, SO or SO₂,
R¹ represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the individual alkyl groups, optionally substituted by halogen or C₁-C Kohlenstoffatalkoxy,
R² stands for halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each optionally substituted by halogen or C₁-C₄alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups,
R³ represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl, each optionally substituted by halogen or C₁-C₄alkoxy, each having 1 to 4 carbon atoms in the individual alkyl groups,
R⁴ individually represents alkyl which is optionally substituted by halogen or C₁-C₄alkoxy and has 1 to 6 carbon atoms,
R⁵ individually represents alkyl optionally substituted by halogen or C₁-C₄alkoxy having 1 to 6 carbon atoms, or
together with R⁴ represents alkanediyl having 2 to 5 carbon atoms, and
R⁶ represents hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl,
and salts of compounds of the formula (I), where the compounds 1- [2- (1,1-dimethoxyethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-t- riazin-2-yl) urea and 1- [2- (1,3-dioxolan-2-ylmethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazine 2-yl) urea are excluded. 2. Compounds of formula (I) according to claim 1, characterized in that therein
A represents nitrogen, CH or C-halogen,
Q represents oxygen, sulfur, SO or SO₂,
R¹ represents hydrogen, fluorine, chlorine, bromine or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each with 1 to 3 carbon atoms in the individual alkyl groups, optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R² stands for fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, each with 1 to 3 carbon atoms in the individual alkyl groups, optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R³ stands for hydrogen, fluorine, chlorine, bromine, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxy carbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each having 1 to 3 carbon atoms in the individual alkyl groups,
R⁴ individually represents alkyl with 1 to 4 carbon atoms optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁵ individually represents alkyl with 1 to 4 carbon atoms optionally substituted by fluorine, chlorine, methoxy or ethoxy, or
together with R⁴ represents alkanediyl having 2 to 4 carbon atoms, and
R⁶ represents hydrogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by fluorine, chlorine, C₁-C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulfinyl or C₁-C₃-alkylsulfonyl,
where the compounds 1- [2- (1,1-dimethoxyethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea and 1- [ 2- (1,3-Dioxolan-2-yl-methyl) -phenylsulfamoyl] -3 (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea are excluded. 3. Compounds of formula (I) according to claim 1, characterized in that therein
A represents nitrogen or CH,
Q represents oxygen or sulfur,
R¹ represents hydrogen, chlorine or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R² represents chlorine or represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R³ stands for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁴ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁵ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or
together with R⁴ stands for ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene), and
R⁶ represents hydrogen or represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl,
where the compounds 1- [2- (1,1-dimethoxyethyl) phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea and 1- [ 2- (1,3-Dioxolan-2-yl-methyl) -phenylsulfamoyl] -3- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) -h-urea are excluded. 4. Compounds of formula (Ia) according to claim 1, in which
Q represents oxygen or sulfur,
R¹ represents hydrogen, chlorine or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R² represents chlorine or represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R³ stands for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁴ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R⁵ individually represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or
together with R⁴ stands for ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene), and
R⁶ for hydrogen or for optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl, methyl, ethyl, n- or i-propyl. 5. A process for the preparation of substituted phenylaminosulfonylureas of the formula (I) according to claim 1, characterized in that aminoazines of the general formula (II) in which
A, R¹ and R² have the meaning given in claim 1,
with chlorosulfonyl isocyanate, if appropriate in the presence of a diluent, and the chlorosulfonylureas formed in this way of the general formula (III) in which
A, R¹ and R² have the meaning given in claim 1,
with substituted anilines of the general formula (IV) in which
Q, R³, R⁴, R⁵ and R⁶ have the meaning given in claim 1,
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. 6. Herbicidal agents, characterized by a content of at least one A compound of formula (I) according to claim 1. 7. Use of compounds of general formula (I) according to claim 1 to combat unwanted plant growth. 8. A method of combating weeds, characterized in that to compounds of the general formula (I) according to claim 1 Weeds or their habitat. 9. A process for the preparation of herbicidal compositions, characterized in that that compounds of the general formula (I) according to Claim 1 with Extenders and / or surfactants mixed.