US20020068681A1

US20020068681A1 - Substituted thienyl(amino)-sulphonyl(thio)ureas as herbicides

Info

Publication number: US20020068681A1
Application number: US09/925,801
Authority: US
Inventors: Ernst Rudolf Gesing; Johannes Jansen; Klaus-Helmut Muller; Ulrich Philipp; Markus Dollinger
Original assignee: Individual
Current assignee: Individual
Priority date: 1996-12-09
Filing date: 2001-08-09
Publication date: 2002-06-06
Anticipated expiration: 2017-11-27
Also published as: US6451738B1; AU5556898A; CN1239868A; CA2274079C; DK0942652T3; BR9714589B1; BR9714589A; DE19651037A1; DE59712211D1; JP2001507681A; EP0942652A1; WO1998025467A1; AU729462B2; CN1191757C; EP0942652B1; CA2274079A1; JP4261621B2; US6303541B1; ES2235263T3

Abstract

The invention relates to novel substituted thienyl(amino)sulphonyl(thio)ureas of the formula (I)

in which

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R¹and R²independently of one another represent hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,

R³represents hydrogen or optionally substituted alkyl,

R⁴and R⁵independently of one another each represent cyano, halogen or represent in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy, and

R⁶represents hydrogen, cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy,

and to salts of compounds of the formula (I), to processes for preparing the novel compounds and to their use as herbicides.

Description

The invention relates to novel substituted thienyl(amino)sulphonyl(thio)ureas, to processes for their preparation and to their use as herbicides.

It is already known that certain substituted thienylsulphonylureas have herbicidal properties (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,398,939, U.S. Pat. No. 4,523,943). However, the herbicidal activity of these known compounds is not satisfactory in all aspects.

This invention, accordingly, provides the novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I)

in which

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R ¹represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,

R ²represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,

R ³represents hydrogen or optionally substituted alkyl,

R ⁴represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy,

R ⁵represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy, and

R ⁶represents hydrogen, cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy,

and salts of compounds of the formula (I).

The novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I) are obtained when

in the case of E representing a single bond in the general formula (I)

(a) aminoazines of the general formula (II)

in which

A, R ¹, R²and R³are each as defined above,

are reacted with thienylsulphonyl iso(thio)cyanates of the general formula (III)

in which

Q, R ⁴, R⁵and R⁶are each as defined above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or

(b) substituted aminoazines of the general formula (IV)

in which

A, Q, R ¹, R²and R³are each as defined above and

Z represents halogen, alkoxy or aryloxy,

are reacted with thiophenesulphonamides of the general formula (V)

in which

R ⁴, R⁵and R⁶are each as defined above,

(c) aminoazines of the general formula (II)

in which

A, R ¹, R²and R³are each as defined above,

are reacted with substituted thiophenesulphon(thio)amides of the general formula (VI)

in which

Q, R ⁴, R⁵and R⁶are each as defined above and

Z represents halogen, alkoxy or aryloxy,

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

or when in the case that E represents an NH grouping

(d) aminoazines of the general formula (II)

in which

A, R ¹, R²and R³are each as defined above

are reacted with chlorosulphonyl iso(thio)cyanate, if appropriate in the presence of a diluent, and the resulting chlorosulphonylureas of the general formula (VII)

in which

A, Q, R ¹, R²and R³are each as defined above

are reacted with aminothiophenes of the general formula (VIII)

in which

R ⁴, R⁵and R⁶are each as defined above,

and the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are optionally converted into salts by customary methods.

The novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I) have strong herbicidal activity.

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

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R ¹represents hydrogen, halogen, represents in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,

R ²represents hydrogen or halogen, represents in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,

R ³represents hydrogen or optionally C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms,

R ⁴represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy,

R ⁵represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy, and

R ⁶represents hydrogen, represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy.

The invention furthermore preferably provides sodium, potassium, magnesium, calcium, ammonium, C ₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, E, Q, R¹, R², R³, R⁴, R⁵and R⁶are each preferably as defined above.

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

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R ¹represents hydrogen, fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethlylamino or diethylamino,

R ²represents fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,

R ³represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl,

R ⁴represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

R ⁵represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy, and

R ⁶represents hydrogen, represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy.

A very particularly preferred group are those compounds of the formula (I) in which

A represents nitrogen or a CH grouping,

E represents a single bond,

Q represents oxygen or sulphur,

R ¹represents hydrogen, fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,

R ³represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl,

R ⁴represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

R ⁵represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy, and

Another very particularly preferred group are those compounds of the formula (I) in which

A represents nitrogen or a CH grouping,

E represents an NH grouping,

Q represents oxygen or sulphur,

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with each other as desired, that is to say combinations between the stated preferred ranges are also possible.

Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and 2-ethyl-4-trifluoromethyl-thien-3-yl-sulphonyl isocyanate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation:

Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 4-ethyl-2-methyl-thiophene-3-sulphonamide as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:

Using, for example, 2-amino-4-chloro-6-methoxy-pyrimidine and N-(2-chloro-4-methyl-thien-3-yl-sulphonyl)-O-phenyl-urethane as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following equation:

Using, for example, 2-amino-4-methoxy-6-methyl-1,3,5-triazine and chlorosulphonyl isocyanate and subsequently 3-amino-4-chloro-2-cyano-thiophene as starting materials, the course of the reaction in process (d) according to the invention can be illustrated by the following equation:

The formula (II) provides a general definition of the aminoazines to be used as starting materials in the process (a) (c) and (d) according to the invention for preparing the compounds of the general formula (I). In the formula (II), A, R ¹, R²and R³each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, R¹, R²and R³.

The aminoazines of the formula (II) are known chemicals for synthesis, some of which are commercially available.

The formula (III) provides a general definition of the thienylsulphonyl iso(thio)cyanates further to be used as starting materials in the process (a) according to the invention. In the formula (III), Q, R ⁴, R⁵and R⁶each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R⁴, R⁵and R⁶.

The starting materials of formula (III) are known and/or can be prepared by processes known per se (cf. EP 30142) and are the subject-matter of a previous application not published before the date of the present application (cf. DE 19650196.2 of Apr. 12, 1996/“Le A 32 173”).

The thienylsulphonyl iso(thio)cyanates of the formula (III) are obtained when thiophenesulphonamides of the general formula (V)—above—are reacted with phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as, for example, butyl isocyanate, if appropriate in the presence of a reaction auxiliary, such as, for example, diazabicyclo[2.2.2]octane, and in the presence of a diluent, such as, for example, toluene, xylene or chlorobenzene, at temperatures between 80° C. and 150° C., and the volatile components are distilled off under reduced pressure after the reaction has ended (cf. the Preparation Examples).

The formula (IV) provides a general definition of the substituted aminoazines to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I). In the formula (IV), A, Q, R ¹, R²and R³each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, Q, R¹, R²or R³; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (IV) are known and/or can be prepared by processes known per se (cf. U.S. Pat. No. 4,690,707, DE 19501174, Preparation Examples).

The formula (V) provides a general definition of the thiophenesulphonamides further to be used as starting materials in the process (b) according to the invention. In the formula (V), R ⁴, R⁵and R⁶each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for R⁴, R⁵and R⁶.

The starting materials of the formula (V) are known and/or can be prepared by processes known per se (cf. EP 30142).

The formula (VI) provides a general definition of the substituted thiophene-sulphon(thio)amides to be used as starting materials in the process (c) according to the invention for preparing the compounds of the formula (I). In the formula (VI), Q, R ⁴, R⁵and R⁶each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R⁴, R⁵and R⁶; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of formula (VI) are known and/or can be prepared by processes known per se.

The formula (VIII) provides a general definition of the aminothiophenes to be used as starting materials in the process (d) according to the invention for preparing the compounds of the formula (I). In the formula (VIII), R ⁴, R⁵and R⁶each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or particularly preferred for R⁴, R⁵and R⁶.

The starting materials of the formula (VIII) are known and/or can be prepared by processes known per se (cf. DE 3303388, U.S. Pat. No. 5,457,085).

Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide.

The processes (a), (b), (c) and (d) according to the invention are preferably carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or dicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the processes (a), (b), (c) and (d) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between −20 C. and +150 C., preferably between 0 C. and +120 C.

The processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

In the practice of the processes (a), (b), (c) and (d) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to employ one of the components in a relatively large excess. The reaction is generally carried out in a suitable solvent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for a number of hours at the temperature required. Work-up is carried out by customary methods (cf. the Preparation Examples).

If required, salts of the compounds of the general formula (I) according to the invention can be prepared. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then be isolated—if required after prolonged stirring—by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weedkillers. By weeds in the broadest sense, there are to be understood all plants which grow in locations 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 be used, for example, in connection with the following plants:

Dicotyledonous 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 and Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and 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 and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

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

The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and railway tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, sports fields and pasture-land and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention are suitable in particular for selectively controlling monocotyledonous and dicotyledonous weeds in monocotyledonous crops, both pre-emergence and post-emergence.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersing agents and/or foam-forming agents.

If the extender used is water, it is also possible to use for example organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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 cyclolhexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-forming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Possible further additives are mineral and vegetable oils.

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

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

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, asulam, atrazine, azimsulfuron, benazolin, benfuresate, bensulfuron(-methyl), bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bromobutide, bromofenoxim, bromoxynil, butachilor, butylate, cafenstrole, carbetamide, chlomethoxyfen, chloramben, chloridazon, chlorimuronl(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clopyralid, clopyrasulfuron, cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, etobenzanid, fenoxaprop(-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, fluazifop(-butyl), flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, fluometuron, fluorocloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, menoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon orbencarb, oryzalin, oxadiazon, oxyfluorfen, paraquat, pendimethalin, plenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propyzamide, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac(-sodium), quinchlorac, quinmerac, quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are 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 customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 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

[0142]
(Process (a)) [0143]
At room temperature (approximately 20° C.), 1.7 g (7.8 mmol) of 2,4-dimethyl-thien-3-yl-sulphonyl isocyanate are added with stirring to a mixture of 1.01 g (7.8 mmol) of 2-amino-4-methoxy-6-methyl-1,3,5-triazine and 40 ml of acetonitrile. The reaction mixture is then heated under reflux for 12 hours and allowed to cool to room temperature. The resulting crystalline product is then isolated by filtration with suction. [0144]
This gives 2.08 g (75% of theory) of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2,4-dimethyl-thien-3-yl-sulplhonyl)-urea of melting point 189° C. [0145]

Example 2

[0146]
(Process (d)) [0147]
2.78 g (19.7 mmol) of chlorosulphonyl isocyanate are dissolved in 200 ml of methylene chloride and cooled to −10° C. A solution of 3.05 g (19.7 mmol) of 2-amino-4,6-dimethoxy-pyrimidine in 50 ml of methylene chloride is then added dropwise with stirring, and the mixture is stirred at 0° C. for 30 minutes. A solution of 2.5 g (10.7 mmol) of 3-amino-2,4-dimethyl-thiophene and 2.0 g (20 mmol) of triethylamine in 100 ml of methylene chloride is subsequently added dropwise. The reaction mixture is then stirred at room temperature (approximately 20° C.) for 15 hours. 100 ml of 1N hydrochloric acid are subsequently added dropwise; the organic phase is separated off, washed with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with ethanol and the resulting crystalline product is isolated by filtration with suction. [0148]
This gives 4.4 g (58% of theory) of N-(4,6-dimethoxy-pyrimidin-2-yl)-N′-(2,4-dimethyl-thien-3-yl-amino-sulphonyl)-urea of melting point 190° C. [0149]

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

TABLE 1


Examples of compounds of the formula (I)

Ex.										Melting
No.	A	E	Q	R¹	R²	R³	R⁴	R⁵	R⁶	point (° C.)

3	N	NH	O	CH₃	OCH₃	H	CH₃	CH₃	H	62
4	N	NH	O	OCH₃	OCH₃	H	CH₃	CH₃	H	170
5	CH	NH	O	Cl	OCH₃	H	CH₃	CH₃	H	100
6	N	—	O	OCH₂CF₃	N(CH₃)₂	H	CH₃	CH₃	H	195
7	CH	—	O	OCH₃	OCH₃	H	CH₃	CH₃	H	198
8	N	—	O	OC₆H₅	N(CH₃)₂	H	CH₃	CH₃	H	173
9	N	—	O	OCH₃	OCH₃	H	CH₃	CH₃	H	168

10	N	—	O	OCH₃		H	CH₃	CH₃	H	180

11	N	—	O	CH₃	SCH₃	H	CH₃	CH₃	H	220
12	N	—	O	CH₃	OC₂H₅	H	CH₃	CH₃	H	144
13	N	—	O	C₂H₅	OCH₃	H	CH₃	CH₃	H	161
14	CH	—	O	CH₃	CH₃	H	CH₃	CH₃	H	240
15	CH	—	O	CH₃	OCH₃	H	CH₃	CH₃	H	140
16	CH	—	O	Cl	OCH₃	H	CH₂	CH₃	H	219

Starting Materials of the Formula (III)

Example (III-1)

[0151]
A mixture of 19.1 g (100 mmol) of 2,4-dimethyl-thiophene-3-sulplonamide, 10.0 g (100 mmol) of butylisocyanate and 100 ml of chloroform is heated to the boil, and at reflux temperature, phosgene is introduced into the mixture for 4 hours. The mixture is subsequently concentrated under water pump vacuum and the residue is subjected to a distillation under oil pump vacuum. [0152]
This gives 10.3 g (47% of theory) of 2,4-dimethyl-thien-3-yl-sulphonyl isocyanate having a boiling range of from 135° C. to 140° C. (at 1 mbar). [0153]

Starting Materials of the Formula (V)

Example (V-1)

Step 1 [0154]
A solution of 13.9 g (109 mmol) of 3-amino-2,4-dimethyl-thiophene in 30 ml of 10% strength hydrochloric acid is cooled to 0° C. and admixed with 50 ml of conc. hydrochloric acid. With cooling to from 0° C. to −5° C., a solution of 8.6 g (125 mmol) of sodium nitrite in 22 ml of water is then added dropwise with stirring. The reaction mixture is stirred at from 0° C. to −5° C. for approximately one hour. Excess sodium nitrite is then destroyed with amidosulphonic acid. The resulting diazonium salt solution is then added dropwise at approximately 15° C. to a solution of 12 g of sulphur dioxide in 100 ml of 1,2-dichloro-ethane. 600 mg of copper(I) chloride and 600 mg of dodecyl-trimethlylammonium bromide are then added, and the reaction mixture is stirred for approximately one hour at approximately 40° C. and for a further 12 hours at room temperature (approximately 20° C.). After addition of 6 g of 30% strength hydrogen peroxide solution, the mixture is stirred for a further 30 minutes. The organic phase is then separated off, washed twice with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with petroleum ether and the resulting crystalline product is isolated by filtration with suction. [0155]
This gives 9.6 g (42% of theory) of 2,4-dimethyl-thiophene-3-sulphonyl chloride of melting point 79° C. [0156]
Step 2 [0157]
A mixture of 6.0 g (29 mmol) of 2,4-dimethyl-thiophene-3-sulphonyl chloride and 30 ml of 25% strength aqueous ammonia solution is stirred at room temperature (approximately 20° C.) for 12 hours. The resulting crystalline product is then isolated by filtration with suction. [0158]
This gives 4.3 g (80% of theory) of 2,4-dimethyl-thiophene-3-sulphonamide of melting point 135° C. [0159]

USE EXAMPLES

Example A

Pre-emergence-Test [0160]
Solvent: 5 parts by weight of acetone [0161]
Emulsifier: 1 part by weight of alkylaryl polyglycol ether [0162]
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. [0163]
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 l of water/ha. [0164]
After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control. [0165]
The figures denote: [0166]
0%=no effect (like untreated control) [0167]
100%=total destruction [0168]

In this test, for example the compounds of Preparation Example 1, 6, 7, 8, 9, 10, 12, 14, 15 and 16 exhibit very strong activity against weeds, and some of them are well tolerated by crop plants, such as, for example, wheat and barley (cf. Tables A-1 to A-10); “ai.” active ingredient (active compound).

TABLE A-1


Pre-emergence Test/Greenhouse

Active compound of	Application rate			Alope-		Ama-	Cheno-	Matri-	Vero-
Preparation Ex. No.	(g of ai./ha)	Barley	Wheat	curus	Lolium	ranthus	podium	caria	nica

	4	0	0	100	100	100	100	100	100

[0170]

TABLE A-2

Pre-emergence Test/Greenhouse

Active compound of Application rate Avena Amaran-

Preparation Ex. No. (g of ai./ha) fatua thus Galium Sinapis

125 80 90 100 90
[0171]

TABLE A-3

Pre-emergence Test/Greenhouse

Active compound of Application rate Echino- Cheno- Matri-

Preparation Ex. No. (g of ai./ha) Wheat chloa Lolium podium caria

60 10 95 95 90 95
[0172]

TABLE A-4

Pre-emergence Test/Greenhouse

Active compound of Application rate Avena Amaran-

Preparation Ex. No. (g of ai./ha) fatua thus Galium Sinapis

125 80 80 90 80
[0173]

TABLE A-5

Pre-emergence Test/Greenhouse

Active compound of Application rate Abuti- Amaran-

Preparation Ex. No. (g of ai./ha) lon thus Sinapis

60 90 90 90
[0174]

TABLE A-6

Pre-emergence Test/Greenhouse

Active compound of Application rate Amaran-

Preparation Ex. No. (g of ai./ha) Setaria thus Galium

60 80 80 100
[0175]

TABLE A-7

Pre-emergence Test/Greenhouse

Active compound of Application rate Alope- Abuti- Ama-

Preparation Ex. No. (g of ai./ha) curus lon ranthus Sinapis

60 80 90 90 90
[0176]

TABLE A-8

Pre-emergence Test/Greenhouse

Active compound of Application rate Amaran-

Preparation Ex. No. (g of ai./ha) Cyperus thus Sinapis

60 100 90 90
[0177]

TABLE A-9

Pre-emergence Test/Greenhouse

Active compound of Application rate Abuti- Amaran-

Preparation Ex. No. (g of ai./ha) lon thus Sinapis

60 100 90 100
[0178]

TABLE A-10

Pre-emergence Test/Greenhouse

Active compound of Application rate Amaran-

Preparation Ex. No. (g of ai./ha) Cyperus thus Sinapis

60 80 95 95

Example B

Post-emergence Test [0179]
Solvent: 5 parts by weight of acetone [0180]
Emulsifier: 1 part by weight of alkylaryl polyglycol ether [0181]
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. [0182]
Test plants which have a height of 5-15 cm are sprayed with the preparation of active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 l of water/ha. [0183]
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. [0184]
The figures denote: [0185]
0%=no effect (like untreated control) [0186]
100%=total destruction [0187]
In this test, for example the compounds of Preparation Example 1, 6, 7, 9, 11, 12, 13, 14, 15 and 16 exhibit strong activity against weeds (cf. Tables B-1 to B-10). [0188]

TABLE B-1

Post-emergence Test/Greenhouse

Active compound of Application rate Ama- Cheno- Matri- Xan-

Preparation Ex. No. (g of ai./ha) Abutilon ranthus podium caria thium

60 95 95 100 95 100
[0189]

TABLE B-2

Post-emergence Test/Greenhouse

Active compound of Application rate Alope- Amaran-

Preparation Ex. No. (g of ai./ha) curus thus Sinapis

125 100 80 100
[0190]

TABLE B-3

Post-emergence Test/Greenhouse

Active compound of Application rate Ama- Cheno- Matri- Xan-

Preparation Ex. No. (g of ai./ha) Abutilon ranthus podium caria thium

60 95 95 95 95 95
[0191]

TABLE B-4

Post-emergence Test/Greenhouse

Active compound of Application rate Abuti- Amaran-

Preparation Ex. No. (g of ai./ha) lon thus Sinapis

60 80 100 95
[0192]

TABLE B-5

Post-emergence Test/Greenhouse

Active compound of Application rate Amaran-

Preparation Ex. No. (g of ai./ha) thus Sinapis

60 100 100
[0193]

TABLE B-6

Post-emergence Test/Greenhouse

Active compound of Application rate Alope- Abuti- Ama-

Preparation Ex. No. (g of ai./ha) curus lon ranthus Sinapis

60 80 90 100 100
[0194]

TABLE B-7

Post-emergence Test/Greenhouse

Active compound of Application rate Abuti- Amaran-

Preparation Ex. No. (g of ai./ha) lon thus Sinapis

60 90 100 95
[0195]

TABLE B-8

Post-emergence Test/Greenhouse

Active compound of Application rate Alope- Ama-

Preparation Ex. No. (g of ai./ha) curus ranthus Sinapis

60 80 100 100
[0196]

TABLE B-9

Post-emergence Test/Greenhouse

Active compound of Application rate Abuti- Ama-

Preparation Ex. No. (g of ai./ha) Setaria lon ranthus Sinapis

60 90 90 100 100
[0197]

TABLE B-10

Post-emergence Test/Greenhouse

Active compound of Application rate

Preparation Ex. No. (g of ai./ha) Amaranthus Sinapis

60 100 95

Claims

1. Substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I)

in which

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R¹represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,

R²represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,

R³represents hydrogen or optionally substituted alkyl,

R⁴represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkeyloxy, alkinyl or alkinyloxy,

R⁵represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkeyloxy, alkinyl or alkinyloxy, and

and salts of compounds of the formula (I).

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

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R¹represents hydrogen, halogen, represents in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,

R²represents hydrogen or halogen, represents in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,

R³represents hydrogen or optionally C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms,

R⁴represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy,

R⁵represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy, and

R⁶represents hydrogen, represents cyano, halogen, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyl or C₂-C₄-alkinyl, represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₄-alkoxy, or represents in each case optionally cyano- or halogen-substituted C₂-C₄-alkenyloxy or C₂-C₄-alkinyloxy, and the sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I).

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

A represents nitrogen or a CH grouping,

E represents a single bond or an NH grouping,

Q represents oxygen or sulphur,

R¹represents hydrogen, fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethlylamino or diethylamino,

R²represents fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,

R³represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl,

R⁴represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

R⁵represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy, and

R⁶represents hydrogen, represents cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy.

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

A represents nitrogen or a CH grouping,

E represents a single bond,

Q represents oxygen or sulphur,

R¹represents hydrogen, fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,

R⁴represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,

R⁵represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl or butinyl, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy, and

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

A represents nitrogen or a CH grouping,

E represents an NH grouping,

Q represents oxygen or sulphur,

6. Process for preparing compounds of formula (I) according to claim 1, characterized in that

in the case of E representing a single bond in the general formula (I)

(a) aminoazines of the general formula (II)

in which

A, R¹, R²and R³are each as defined in claim 1,

in which

Q, R⁴, R⁵and R⁶are each as defined in claim 1,

if appropriate in the presence of reaction auxiliary and if appropriate in the presence of a diluent, or

(b) substituted aminoazines of the general formula (IV)

in which

A, Q, R¹, R²and R³are each as defined in claim 1 and

Z represents halogen, alkoxy or aryloxy,

are reacted with thiophenesulphonamides of the general formula (V)

in which

R⁴, R⁵and R⁶are each as defined above,

(c) aminoazines of the general formula (II)

in which

A, R¹, R²and R³are each as defined above,

in which

Q, R⁴, R⁵and R⁶are each as defined above and

Z represents halogen, alkoxy or aryloxy,

or in that in the case of E representing an NH grouping

(d) aminoazines of the general formula (II)

in which

A, R¹, R²and R³are each as defined above

in which

A, Q, R¹, R²and R³are each as defined above are reacted with aminothiophenes of the general formula (VIII)

in which

R⁴, R⁵and R⁶are each as defined above,

7. Herbicidal compositions, characterized in that they comprise at least one compound of the formula (I) or one of its salts according to claim 1.

8. The use of compounds of the general formula (I) or salts thereof according to claim 1 for controlling undesirable plant growth.

9. Method for controlling weeds, characterized in that compounds of the general formula (I) or salts thereof according to claim 1 are allowed to act on the weeds or their habitat.

10. Process for preparing herbicidal compositions, characterized in that compounds of the general formula (I) or salts thereof according to claim 1 are mixed with extenders and/or surfactants.