Indian Patents. 221178:SUBSTITUTED THIENYL(AMINO)SULPHONYLUREAS OF THE GENERAL FORMULA (I), ITS PROCESS OF PREPARATION AND THE HERBICIDAL COMPOSITION COMPRISING THE SAME

Title of Invention	SUBSTITUTED THIENYL(AMINO)SULPHONYLUREAS OF THE GENERAL FORMULA (I), ITS PROCESS OF PREPARATION AND THE HERBICIDAL COMPOSITION COMPRISING THE SAME
Abstract	The invention relates to thienyl(amino)sulfonylureas of formula (I), wherein A, Q, R?1¿, R?2¿, R?3¿, R?4¿ and R?5¿ have the meaning given in the description, and to a method for the preparation of said compounds and their use as herbicides.

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003 COMPLETE SPECIFICATION [See Section 10; rule 13] SUBSTITUTED THIENYL(AMINO)SULPHONYLUREAS OF THE GENERAL FORMULA (I), ITS PROCESS OF PREPARATION AND THE HERBICIDAL COMPOSITION COMPRISING THE SAME" BAYER AKTIENGESELLSCHAFT, a German company, of D-51368, Leverkusen, Germany, The following specification particularly describes the invention and the manner in which it is to be performed: GRANTED ORIGINAL 640/MUM/2000 5-3-2008 Le A 33 917-Foreign Countries Lu/ngb/NT 10 Substituted thienyl(amino)sulphonylureas The invention relates to novel substituted thienyl(amino)sulphonylureas, to processes for their preparation and to their use as herbicides. It is already known that certain substituted thienylsulphonylureas have herbicidal properties (cf. EP-A-30142 / US-A-4481029 / US-A-4599103 / US-A-4701535, EP-A-97122 / US-A-4549898, EP-A-207609 / US-A-4668281). However, the herbicidal activity of these known compounds is not entirely satisfactory. This invention, accordingly, provides the novel substituted thienyl(amino)sulphonyl-ureas of the general formula (I) 15 in which 20 A represents nitrogen or a CH grouping, Q represents a single bond or represents NH, R1 represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, aryloxy or heterocyclyloxy, R2 represents hydrogen, halogen or in each case optionally substituted alkyl, 25 alkoxy, alkylthio, alkylamino, dialkylamino, aryloxy or heterocyclyloxy, R3 represents hydrogen or optionally substituted alkyl, Le A 33 917-Foreign Countries R4 represents halogen or optionally substituted alkyl and - if Q represents NH -also represents hydrogen, and 5 R5 represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl or heterocyclyl, and salts of compounds of the formula (I). 10 Saturated or unsaturated hydrocarbon groupings, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched as far as this is possible - including in combination with hetero atoms, such as in alkoxy. Optionally substituted radicals can be mono- or polysubstituted, where in the case of 15 polysubstitution the substituents can be identical or different. Preferred substituents or ranges of the radicals which are present in the formulae given above and below are defined below. 20 A preferably represents nitrogen or a CH grouping. Q preferably represents a single bond or represents NH. R1 preferably represents hydrogen, represents halogen, represents in each case 25 optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkyl- thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy. 30 Le A 33 917-Foreign Countries R2 preferably represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkyl- thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, 5 C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy. R3 preferably represents hydrogen or represents optionally C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 10 to 4 carbon atoms. R4 preferably represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms and - if Q represents NH - also represents hydrogen. 15 R5 preferably represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- 20 or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetra-hydrofuryl. 25 A particularly preferably represents nitrogen or a CH grouping. Q particularly preferably represents a single bond or represents NH. 30 R1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano-, fluorine-, chlorine-, Le A 33 917-Foreign Countries 10 15 methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl¬amino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino. R2 particularly preferably represents fluorine, chlorine, bromine, or represents 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. R3 particularly preferably represents hydrogen or represents in each case optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl- substituted methyl or ethyl. R4 particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. 20 R5 particularly preferably represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, 25 chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl. A very particularly preferably represents nitrogen or a CH grouping. 30 Q very particularly preferablytepresents a single bond or represents NH. Le A 33 917-Foreign Countries R1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy- substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methyl- 5 amino, ethylamino, or represents dimethylamino. R2 very particularly preferably represents fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino or ethyl- 10 amino, or represents dimethylamino. R3 very particularly preferably represents hydrogen or methyl. R4 very particularly preferably represents in each case optionally fluorine- or 15 chlorine-substituted methyl, ethyl, n- or i-propyl. R5 very particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluorine- or chlorine-substituted propenyl or 20 propinyl. A most preferably represents a CH grouping. R1and R2most preferably represent methoxy. 25 R3 most preferably represents hydrogen. The invention also preferably provides the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4- 30 alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5or C6-cycloalkyl-ammonium- and di-(C1-C2-alkyl)-benzyl-ammonium salts of Le A 33 917-Foreign Countries compounds of the formula (I), in which A, Q, R1, R2, R3, R4 AND R5 HAVE ME meaning given above as being preferred. The abovementioned general or preferred radical definitions apply both to the end 5 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 one another as desired, i.e. including combinations between the given ranges of preferred compounds. 10 Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being preferred. Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being 15 particularly preferred. Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. 20 Most preference according to the invention is given to the compounds in which R , 2 3 R , R or A have one of the meanings given as being most preferred. Examples of the compounds of the formula (I) according to the invention are listed in 25 the groups below. Le A 33 917-Foreign Countries Group 1 Here, A, Q, R1, R2 and R3 have, for example, the meanings listed below: Group 2 Le A 33 917-Foreign Countries Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10 15 Le A 33 917-Foreign Countries Group 3 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 4 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 5 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10 15 Le A 33 917-Foreign Countries Group 6 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 7 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 8 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10 15 Le A 33 917-Foreign Countries Group 9 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 10 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 11 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Le A 33 917-Foreign Countries Group 12 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 5 1. Group 13 10 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 14 15 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Le A 33 917-Foreign Countries Group 15 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 16 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10 Group 17 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 15 1. 10 15 Le A 33 917-Foreign Countries Group 18 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 19 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 20 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Le A 33 917-Foreign Countries Group 21 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 22 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 10 1. Group 23 15 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Le A 33 917-Foreign Countries Group 24 5 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 25 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10 The novel substituted thienyl(amino)sulphonylureas of the general formula (I) have strong herbicidal activity. The novel substituted thienyl(amino)sulphonylureas of the general formula (I) are 15 obtained when (a) aminoazines of the general formula (II) 5 Le A 33 917-Foreign Countries in which A, R1 and R2 are each as defined above are reacted with thienyl(amino)sulphonyl isocyanates of the general formula (III) in which 10 15 20 Q, R4 and R5 are each as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or when (b) substituted aminoazines of the general formula (IV) in which Le A 33 917-Foreign Countries A, R1 and R2 are each as defined above, Z represents halogen, alkoxy or aryloxy and 5 3 R has the meaning given above for R or represents the grouping -C(0)-Z, are reacted with thiophene derivatives of the general formula (V) 10 in which Q, R4 and R5 are each as defined above, 15 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or when 20 (c) aminoazines of the general formula (II) in which 25 A, R1 and R2 are each as defined above, Le A 33 917-Foreign Countries are reacted with thiophene derivatives of the general formula (VI) 5 in which 10 15 Q, R4 and R5 are 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 (d) aminoazines of the general formula (II) (II) in which 20 A, R1 and R2 are each as defined above, 25 are reacted with chlorosulphonyl isocyanate, if appropriate in the presence of a diluent, and the resulting chlorosulphonylaminocarbonylamino-azines of the general formula (VII) Le A 33 917-Foreign Countries in which 5 A, R1 and R2 are each as defined above are - after intermediate isolation or "in situ" - reacted with substituted aminothiophenes of the general formula (VIII) 10 in which R4 and R5 are each as defined above, 15 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are, if 20 appropriate, converted by customary methods into salts. Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and 4-ethoxycarbonyl- 2-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 25 following formula scheme: Le A 33 917-Foreign Countries Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-ethyl-4-i-propoxycarbonyl-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 formula scheme: 10 Using, for example, 2-amino-4-chloro-6-methoxy-pyrimidine and O-phenyl N-(4-ethoxycarbonyl-2-methyl-thien-3-yl-sulphonyl)-urethane as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme: 15 20 Using, for example, 2-amino-4-methoxy-6-trifluoromethyl-pyrimidine, chloro-sulphonyl isocyanate and ethyl 3-amino-2-ethyl-thiophene-4-carboxylate as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme: Le A 33 917-Foreign Countries The formula (II) provides a general definition of the aminoazines to be used as starting materials in the processes (a), (c) and (d) according to the invention for 5 preparing the compounds of the general formula (I). In the formula (II), A, R1 and R2 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for A, R1 and R2. 10 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 thienyl(amino)sulfonyl isocyanates further to be used as starting materials in the process (a) according to the 15 invention. In the formula (III), Q, R4 and R5 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5. 20 The starting materials of the formula (III) are known and/or can be prepared by processes known per se (cf. EP 30142 / US-A-4481029 / US-A-4599103 / US-A-4701535). Le A 33 917-Foreign Countries The thienyl(amino)sulphonyl isocyanates of the formula (III) are obtained when thiophene derivatives 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 5 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, after the reaction has ended, distilled off under reduced pressure. 10 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 the compounds of the formula (I). In the formula (IV), A, R1 and R2 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being 15 preferred or as being particularly preferred for A, R1 and R2; 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 20 processes known per se (cf. US 4 690 707, DE 19 501 174). The formula (V) provides a general definition of the thiophene derivatives further to be used as starting materials in the process (b) according to the invention. In the formula (V), Q, R4 and R5 each preferably or in particular have those meanings 25 which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5. The starting materials of the formula (V) are known and/or can be prepared by 30 processes known per se (cf. EP 30 142 / US-A-4 481 029 / US-A-4 599 103 / US-A- 4 701 535, Preparation Examples). Le A 33 917-Foreign Countries The formula (VI) provides a general definition of the substituted thiophene derivatives 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, R4 5 and R5 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5; Z preferably represents fluorine, chlorine, bromine, Cj-C^alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy. 10 The starting materials of the formula (VI) are known and/or can be prepared by processes known per se. The formula (VIII) provides a general definition of the substituted aminothiophenes 15 to be used as starting materials in the process (d) according to the invention for preparing compounds of the general formula (I). In the general formula (VIII), R4 and R5 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly 20 preferred for R4 and R5. The starting materials of the general formula (VIII) are known and/or can be prepared by processes known per se (cf. Aust. J. Chem. 48 (1995), 1907-1916). 25 Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are especially 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 30 as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or Le A 33 917-Foreign Countries methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylform-anilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, and sulphoxides, such as dimethyl sulphoxide. 5 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 10 bicarbonates, 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, 15 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 20 reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures between -20°C and +150°C, preferably between -10°C and +120°C. The processes (a), (b), (c) and (d) according to the invention are generally carried out 25 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. For carrying out the processes (a), (b), (c) and (d) according to the invention, the 30 starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components. Le A 33 917-Foreign Countries The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples). 5 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 methods for forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, 10 acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can then - if appropriate after prolonged stirring - be isolated by concentration or filtering off with suction. The active compounds according to the invention can be used as defoliants, 15 desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. 20 The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, 25 Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, 30 Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Le A 33 917-Foreign Countries Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. 5 Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, 10 Scirpus, Setaria, Sorghum. Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. 15 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 active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and 20 railway tracks, and on paths and squares with or without tree plantings. Equally, the active compounds according to the invention can be employed for the control of 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 25 fields, in lawns, turf and pasture-land, and for the selective control of weeds in annual crops. The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts 30 of plants. To a certain extent, they are also suitable for the selective control of Le A 33 917-Foreign Countries monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledo¬nous crops, both pre-emergence and post-emergence. The active compounds can be converted into the customary formulations, such as 5 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. 10 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 dispersants and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic 15 solvents as auxiliary solvents. Suitable liquid solvents are essentially the following: 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 20 glycol and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and also water. Suitable solid carriers are: for example ammonium salts and ground natural minerals, 25 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 30 sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example nonionic and anionic emulsifiers, such as Le A 33 917-Foreign Countries 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. 5 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, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are 10 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, 15 copper, cobalt, molybdenum and zinc. The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%. 20 For the control of weeds, the active compounds according to the invention, as such or in 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 25 acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromo- 30 butide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, Le A 33 917-Foreign Countries chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop- (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, 5 cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), 10 ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, 15 flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-methyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufo-sinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop-(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, 20 imazosulfuron, iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, meto-sulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, 25 naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, 30 pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, sirhazihe, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thia-fluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron. A mixture with other known active compounds, such as fungicides, .insecticides, acaricides, nematicides, bird repellents, 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 ias 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 relatively wide 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 present invention relates to substituted thienyl(amino)sulphonylures of the general formula (I) in which A represents nitrogen, Q represents a single bond or represents NH, R1 represents hydrogen, represents 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, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy, R2 represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylmino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy- substituted phenoxy, oxetanyloxy, furyloxy or tetahydrofuryloxy, R3 represents hydrogen or represents optionally C1-C4alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms, R4 represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, and R5 represents hydrogen, represents optionally cyano-, halogen- or C1-C4 alkoxy- substituted alkyl haying 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyi or cycloalkylalkyl having in/each case 3 to 6 carbon atoms in the cycloalkyi groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl. 25 ...The preparation and use of the active compounds according to the invention can be seen from the following examples below. Le A 33 917-Foreign Countries Preparation Examples: Example 1 5 (Process (b)) 0.75 g (2,9 mmol) of 2-phenoxycarbonylamino-4-methoxy-6-methyl-l,3,5-triazine is dissolved in 40 ml of acetonitrile and admixed successively with 0.75 g (3,2 mmol) of methyl 2-methyl-3-sulphamoyl-thiophene-4-carboxylate and 0.49 g (3.2 mmol) of 10 diazabicycloundecene (DBU). The reaction mixture is stirred at room temperature (about 20°C) for 12 hours and then concentrated under water-pump vacuum. The residue is taken up in methylene chloride and the mixture is washed with 2N hydrochloric-acid and with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with 15 diethyl ether and the resulting crystalline product is isolated by filtration with suction. This gives 0.60 g (52% of theory) of N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(4-methoxycarbonyl-2-methyl-thien-3-yl-sulphonyl)-urea of melting point 195°C. 20 (Process (d)) Example 2 Le A 33 917-Foreign Countries 1.05 g (7.5 mmol) of chlorosulphonyl isocyanate are initially charged in 75 ml of methylene chloride. After cooling to -10°C, a solution of 1.16 g (7.5 mmol) of 2-amino-4,6-dimethoxy-pyrimidine in 30 ml of methylene chloride is added 5 dropwise with stirring to this mixture, and the mixture is stirred at -10°C for 30 minutes. At 0°C, a solution of 1.28 g (7.5 mmol) of methyl 3-amino-2-methyl- thiophene-4-carboxylate and 0.75 g (7.5 mmol) of triethylamine in 50 ml of methylene chloride is then added dropwise, and the reaction mixture is stirred at room temperature (about 20°C) for 12 hours. 100 ml of water in 100 ml of 2N 10 hydrochloric acid are then added and the organic phase is separated off, washed with 50 ml of water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum and the residue is crystallized from ethanol. This gives 2.1 g (66% of theory) of N-(4,6-dimethoxy-pyrimidin-2-yl)-N"- 15 (4-methoxycarbonyl-2-methyl-thien-3-yl-amino-sulphonyl)-urea of melting point 174°C. Analogously to Examples 1 and 2, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for 20 example, the compounds of the general formula (I) listed in Table 1 below. Le A 33 917-Foreign Countries Table 1: Examples of the compounds of the formula (I) Ex. No. A Q R1 R2 R3 R4 R5 Melting point (°Q 3 CH NH OCH3 OCH3 H n-C3H7 C2H5 140 4 CH NH OCH3 OCH3 H i-C3H7 C2H5 154 5 CH NH OCH3 OCH3 H C2H5 CH3 195 6 CH - OCH3 OCH3 H CH3 CH3 194 Starting materials of the formula (V): Example (V-l) 10 Step 1 At from 0°C to 5°C, a solution of 19.9 g (0.29 mol) of sodium nitrite in 60 ml of water is added dropwise with stirring to a solution of 42.7 g (0.25 mol) of methyl 15 3-amino-2-methyl-thiophene-4-carboxylate in 75 ml of 10% strength aqueous hydrochloric acid. The reaction mixture is stirred at from 0°C to 5°C for 60 minutes. The excess of nitrite is subsequently destroyed using amidosulphonic acid. At from 0°C to 5°C, the mixture is then added dropwise with stirring to a solution of 35 g (0.55 mol) of sulphur dioxide in 300 ml of methylene chloride. After addition of Le A 33 917-Foreign Countries 1.5 g of copper(I) chloride and 1.5 g of dodecyl-trimethylammonium bromide, the reaction mixture is stirred at 40°C for 60 minutes and then at 20°C for 12 hours. 18 ml of 35% strength aqueous hydrochloric acid are then added, the mixture is stirred at 20°C for 4 hours and the phases are then separated. The aqueous phase is 5 re-extracted with methylene chloride and the combined organic phases are washed with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum and the residue is crystallized from hexane. This gives 51.7 g (81% of theory) of 4-methoxycarbonyl-2-methyl-thiophene-3- 10 sulphonyl chloride. Step 2 15 A mixture of 45 g (177 mmol) of 4-methoxycarbonyl-2-methyl-thiophene-3- sulphonyl chloride, 34 g (354 mmol) of ammonium carbonate and 400 ml of methylene chloride is stirred at room temperature (about 20°C) for 12 hours. The mixture is filtered and the solvent is distilled off from the filtrate under water-pump vacuum, the residue is digested with diethyl ether and the crystalline product is 20 isolated by filtration with suction. This gives 21.5 g (52% of theory) of 4-methoxycarbonyl-2-methyl-thiophene-3-sulphonamide. Le A 33 917-Foreign Countries -Use Examples: Example A 5 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether 10 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. 15 Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare. 20 After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: 25 0 % = no effect (like untreated control) 100% = total destruction In this test, for example, the compounds of Preparation Examples 1, 2, 3, 4, 5 and 6 30 show very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, cotton, maize and soya. Table Al: Pre-emergence test/greenhouse r a> > -J I o TO P n o c 3 CO Icn Table A2: Pre-emergence test/greenhouse Table A3: Pre-emergence test/greenhouse Table A4: Pre-emergence test/greenhouse Table A5: Pre-emergence test/greenhouse Table A6: Pre-emergence test/greenhouse Le A 33 917-Foreign Countries Example B Post-emergence test 5 Solvent: 5 parts by weight of acetone Emulsifier. 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of 10 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 preparation of active compound such that the particular amounts of active compound desired are applied 15 per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 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. 20 The figures denote: 0 % = no effect (like untreated control) 100% = total destruction 25 In this test, for example, the compounds of Preparation Examples 1, 2, 5 and 6 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, barley and wheat. Table Bl: Post-emergence test/greenhouse r CD -J 1 o D n o c 3 a> en Table B2: Post-emergence test/greenhouse Table B3: Post-emergence test/greenhouse Table B4: Post-emergence test/greenhouse WE CLAIM: Substituted thienyl(amino)sulphonylureas of the general formula (I) in which A represents nitrogen, Q represents a single bond or represents NH, R1 represents hydrogen, represents 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, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy, R2 represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylmino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy- substituted phenoxy, oxetanyloxy, furyloxy or tetahydrofuryloxy, R3 represents hydrogen or represents optionally C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms, R4 represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, and R5 represents hydrogen, represents optionally cyano-, halogen- or C1-C4 alkoxy-substituted alkyl haying 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl. 2. Substituted thienyl(amino)sulphonylureas as claimed in claim 1, wherein R1 represents hydrogen, fluorine, chlorine, bromine, iodine, or represents 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, R2 represents fluorine, chlorine, bromine, or represents 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, R3 represents hydrogen or represents in each case optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl, R4 represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, and R5 represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl. 3. Substituted thienyl(arnino)sulphonylureas as claimed in claim 1, wherein R1 represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, or represents dimethylaminOj R2 represents fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy , ethoxy, methylthio, ethylthio, methylamino or ethylamino, or represents dimethylamino, R3 represents hydrogen or methyl, R4 represents in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n-or i-propyl, and R5 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-siibstituted methyl, ethyl, n-or i-propyl, or represents in each ease optionally fluorine- or chlorine-substituted propenyl or propinyl. 4. 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 as claimed in any one of claim 1 to 4. 5. Process for preparing compounds as claimed in any of claims 1 to 4, wherein (a) aminoazines of the general formula (II) in which A, R1 and R2 are each as defined in any of claims 1 to 3 are reacted with thienyl(amino)sulphonyl isocyanates of the general formula (III) in which Q, R4 and R5 are each as defined in any of claims 1 to 3, in the presence of a reaction auxiliary, of the kind such as herein described and in the presence of a diluent, of the kind such as herein described, wherein the process is carried out under atmospheric pressure and at temperatures between -20°C and +150°C. 6. Process for preparing compounds as claimed in any of claim 1 to 4 wherein, substituted aminoazines of the general formula (IV) in which A, R1 and R2 are each as defined in any of claims 1 to 3, Z represents halogen, alkoxy or aryloxy and R has the meaning given for R3 in any of claims 1 to 3 represents the grouping -C(OJ-Z, are reacted with thiophene derivatives of the general formula (V) in which Q, R4 and R5 are each as defined in any of claims 1 to 3, in the presence of a reaction auxiliary, of the kind such as herein described and in the presence of a diluent, of the kind such as herein described, wherein the process is carried out under atmospheric pressure and at temperatures between -20°C and +1500C. 7. Herbicidal composition, wherein it comprises a compound as claimed in any of claims 1 to 5 between 0.1 and 95% by weight and customary extenders and/or surfactants, of the kind such as herein described. 8. Compounds of the general formula I substantially as herein described with reference to the forgoing examples. 9. Herbicidal composition substantially as herein described with reference to the foregoing examples. Dated this on July 10, 2000 (DR. ANUSHRI GUPTA) OF REMFRY & SAGAR ATTORNEY FOR THE APPLICANTS

Full Text

FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
[See Section 10; rule 13]
SUBSTITUTED THIENYL(AMINO)SULPHONYLUREAS OF THE GENERAL
FORMULA (I), ITS PROCESS OF PREPARATION AND THE HERBICIDAL
COMPOSITION COMPRISING THE SAME"
BAYER AKTIENGESELLSCHAFT, a German company, of D-51368, Leverkusen, Germany,
The following specification particularly describes the invention and the manner in which it is to be performed:

GRANTED
ORIGINAL
640/MUM/2000 5-3-2008

Le A 33 917-Foreign Countries Lu/ngb/NT

10

Substituted thienyl(amino)sulphonylureas
The invention relates to novel substituted thienyl(amino)sulphonylureas, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted thienylsulphonylureas have herbicidal properties (cf. EP-A-30142 / US-A-4481029 / US-A-4599103 / US-A-4701535, EP-A-97122 / US-A-4549898, EP-A-207609 / US-A-4668281). However, the herbicidal activity of these known compounds is not entirely satisfactory.
This invention, accordingly, provides the novel substituted thienyl(amino)sulphonyl-ureas of the general formula (I)

15 in which

20

A represents nitrogen or a CH grouping,
Q represents a single bond or represents NH,
R1 represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, aryloxy or heterocyclyloxy,

R2 represents hydrogen, halogen or in each case optionally substituted alkyl,
25 alkoxy, alkylthio, alkylamino, dialkylamino, aryloxy or heterocyclyloxy,
R3 represents hydrogen or optionally substituted alkyl,

Le A 33 917-Foreign Countries
R4 represents halogen or optionally substituted alkyl and - if Q represents NH -also represents hydrogen, and
5 R5 represents hydrogen or in each case optionally substituted alkyl, alkenyl,
alkinyl, cycloalkyl, cycloalkylalkyl or heterocyclyl,
and salts of compounds of the formula (I).
10 Saturated or unsaturated hydrocarbon groupings, such as alkyl, alkenyl or alkinyl, are
in each case straight-chain or branched as far as this is possible - including in combination with hetero atoms, such as in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of
15 polysubstitution the substituents can be identical or different.
Preferred substituents or ranges of the radicals which are present in the formulae given above and below are defined below.
20 A preferably represents nitrogen or a CH grouping.
Q preferably represents a single bond or represents NH.
R1 preferably represents hydrogen, represents halogen, represents in each case
25 optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkyl-
thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy. 30

Le A 33 917-Foreign Countries
R2 preferably represents hydrogen, represents halogen, represents in each case
optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkyl-
thio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in
the alkyl groups, or represents in each case optionally cyano-, halogen-,
5 C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or
tetrahydrofuryloxy.
R3 preferably represents hydrogen or represents optionally C1-C4-alkoxy-,
C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1
10 to 4 carbon atoms.
R4 preferably represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms and - if Q represents NH - also represents hydrogen.
15
R5 preferably represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen-
20 or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case
3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetra-hydrofuryl.
25
A particularly preferably represents nitrogen or a CH grouping.
Q particularly preferably represents a single bond or represents NH.
30 R1 particularly preferably represents hydrogen, fluorine, chlorine, bromine,
iodine, or represents in each case optionally cyano-, fluorine-, chlorine-,

Le A 33 917-Foreign Countries

10
15

methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl¬amino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
R2 particularly preferably represents fluorine, chlorine, bromine, or represents 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.
R3 particularly preferably represents hydrogen or represents in each case
optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or
i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-
substituted methyl or ethyl.
R4 particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

20 R5 particularly preferably represents hydrogen, represents in each case optionally
cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-,
25 chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
A very particularly preferably represents nitrogen or a CH grouping.
30
Q very particularly preferablytepresents a single bond or represents NH.

Le A 33 917-Foreign Countries
R1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine,
represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methyl-
5 amino, ethylamino, or represents dimethylamino.
R2 very particularly preferably represents fluorine, chlorine, bromine, represents
in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino or ethyl-
10 amino, or represents dimethylamino.
R3 very particularly preferably represents hydrogen or methyl.
R4 very particularly preferably represents in each case optionally fluorine- or
15 chlorine-substituted methyl, ethyl, n- or i-propyl.
R5 very particularly preferably represents in each case optionally fluorine-,
chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or
represents in each case optionally fluorine- or chlorine-substituted propenyl or
20 propinyl.
A most preferably represents a CH grouping.

R1and R2most preferably represent methoxy.
25
R3 most preferably represents hydrogen.
The invention also preferably provides the sodium, potassium, magnesium, calcium,
ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4-
30 alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium,
C5or C6-cycloalkyl-ammonium- and di-(C1-C2-alkyl)-benzyl-ammonium salts of

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compounds of the formula (I), in which A, Q, R1, R2, R3, R4 AND R5 HAVE ME meaning given above as being preferred.
The abovementioned general or preferred radical definitions apply both to the end
5 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 one another as desired, i.e. including combinations between the given ranges of preferred compounds.
10 Preference according to the invention is given to those compounds of the formula (I)
which contain a combination of the meanings given above as being preferred.
Particular preference according to the invention is given to those compounds of the
formula (I) which contain a combination of the meanings given above as being
15 particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. 20
Most preference according to the invention is given to the compounds in which R ,
2 3 R , R or A have one of the meanings given as being most preferred.
Examples of the compounds of the formula (I) according to the invention are listed in
25 the groups below.

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Group 1

Here, A, Q, R1, R2 and R3 have, for example, the meanings listed below:

Group 2

Le A 33 917-Foreign Countries

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

10
15

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Group 3
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 4
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 5

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

10
15

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Group 6
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 7
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 8

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

10
15

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Group 9
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 10
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 11
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

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Group 12
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group
5 1.
Group 13

10 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 14

15 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

Le A 33 917-Foreign Countries

Group 15
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 16

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
10
Group 17

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group
15 1.

10
15

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Group 18
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 19
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 20

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

Le A 33 917-Foreign Countries

Group 21
Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.
Group 22

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group
10 1.
Group 23

15 Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1.

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Group 24

5

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. Group 25

Here, A, Q, R1, R2 and R3 have, for example, the meaning given above in Group 1. 10
The novel substituted thienyl(amino)sulphonylureas of the general formula (I) have strong herbicidal activity.
The novel substituted thienyl(amino)sulphonylureas of the general formula (I) are
15 obtained when
(a) aminoazines of the general formula (II)

5

Le A 33 917-Foreign Countries

in which
A, R1 and R2 are each as defined above

are reacted with thienyl(amino)sulphonyl isocyanates of the general formula (III)

in which
10

15
20

Q, R4 and R5 are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted aminoazines of the general formula (IV)

in which

Le A 33 917-Foreign Countries
A, R1 and R2 are each as defined above,
Z represents halogen, alkoxy or aryloxy and
5
3 R has the meaning given above for R or represents the grouping -C(0)-Z,
are reacted with thiophene derivatives of the general formula (V)

10

in which
Q, R4 and R5 are each as defined above,
15 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence
of a diluent,
or when
20 (c) aminoazines of the general formula (II)

in which
25 A, R1 and R2 are each as defined above,

Le A 33 917-Foreign Countries
are reacted with thiophene derivatives of the general formula (VI)

5 in which

10
15

Q, R4 and R5 are 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
(d) aminoazines of the general formula (II)

(II)

in which
20
A, R1 and R2 are each as defined above,

25

are reacted with chlorosulphonyl isocyanate, if appropriate in the presence of a diluent, and the resulting chlorosulphonylaminocarbonylamino-azines of the general formula (VII)

Le A 33 917-Foreign Countries

in which
5 A, R1 and R2 are each as defined above
are - after intermediate isolation or "in situ" -
reacted with substituted aminothiophenes of the general formula (VIII)
10

in which
R4 and R5 are each as defined above,
15
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are, if
20 appropriate, converted by customary methods into salts.
Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and 4-ethoxycarbonyl-
2-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
25 following formula scheme:

Le A 33 917-Foreign Countries

Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-ethyl-4-i-propoxycarbonyl-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 formula scheme:

10

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

15

20

Using, for example, 2-amino-4-methoxy-6-trifluoromethyl-pyrimidine, chloro-sulphonyl isocyanate and ethyl 3-amino-2-ethyl-thiophene-4-carboxylate as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme:

Le A 33 917-Foreign Countries

The formula (II) provides a general definition of the aminoazines to be used as
starting materials in the processes (a), (c) and (d) according to the invention for
5 preparing the compounds of the general formula (I). In the formula (II), A, R1 and R2
each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for A, R1 and R2.
10 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 thienyl(amino)sulfonyl
isocyanates further to be used as starting materials in the process (a) according to the
15 invention. In the formula (III), Q, R4 and R5 each preferably or in particular have
those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5.
20 The starting materials of the formula (III) are known and/or can be prepared by
processes known per se (cf. EP 30142 / US-A-4481029 / US-A-4599103 / US-A-4701535).

Le A 33 917-Foreign Countries

The thienyl(amino)sulphonyl isocyanates of the formula (III) are obtained when
thiophene derivatives 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
5 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, after the reaction has ended, distilled off under reduced pressure.
10 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 the compounds of the formula (I). In the formula (IV), A, R1 and R2 each preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I), as being
15 preferred or as being particularly preferred for A, R1 and R2; 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
20 processes known per se (cf. US 4 690 707, DE 19 501 174).
The formula (V) provides a general definition of the thiophene derivatives further to
be used as starting materials in the process (b) according to the invention. In the
formula (V), Q, R4 and R5 each preferably or in particular have those meanings
25 which have already been mentioned above, in connection with the description of the
compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5.
The starting materials of the formula (V) are known and/or can be prepared by
30 processes known per se (cf. EP 30 142 / US-A-4 481 029 / US-A-4 599 103 / US-A-
4 701 535, Preparation Examples).

Le A 33 917-Foreign Countries
The formula (VI) provides a general definition of the substituted thiophene
derivatives 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, R4
5 and R5 each preferably or in particular have those meanings which have already been
mentioned above, in connection with the description of the compounds of the formula (I), as being preferred or as being particularly preferred for Q, R4 and R5; Z preferably represents fluorine, chlorine, bromine, Cj-C^alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy. 10
The starting materials of the formula (VI) are known and/or can be prepared by processes known per se.
The formula (VIII) provides a general definition of the substituted aminothiophenes
15 to be used as starting materials in the process (d) according to the invention for
preparing compounds of the general formula (I). In the general formula (VIII), R4
and R5 each preferably or in particular have those meanings which have already been
mentioned above, in connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred or as being particularly
20 preferred for R4 and R5.
The starting materials of the general formula (VIII) are known and/or can be prepared by processes known per se (cf. Aust. J. Chem. 48 (1995), 1907-1916).
25 Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the
invention are especially 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
30 as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol
dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or

Le A 33 917-Foreign Countries
methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylform-anilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, and sulphoxides, such as dimethyl sulphoxide. 5
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
10 bicarbonates, 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,
15 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
20 reaction temperatures can be varied within a relatively wide range. In general, the
processes are carried out at temperatures between -20°C and +150°C, preferably between -10°C and +120°C.
The processes (a), (b), (c) and (d) according to the invention are generally carried out
25 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.
For carrying out the processes (a), (b), (c) and (d) according to the invention, the
30 starting materials are generally employed in approximately equimolar amounts.
However, it is also possible to use a relatively large excess of one of the components.

Le A 33 917-Foreign Countries
The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples). 5
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
methods for forming salts, for example by dissolving or dispersing a compound of
the formula (I) in a suitable solvent, such as, for example, methylene chloride,
10 acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can
then - if appropriate after prolonged stirring - be isolated by concentration or filtering off with suction.
The active compounds according to the invention can be used as defoliants,
15 desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest
sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
20 The active compounds according to the invention can be used, for example, in
connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,
25 Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,
30 Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Le A 33 917-Foreign Countries
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
5 Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,
Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,
Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,
Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
10 Scirpus, Setaria, Sorghum.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
15 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 active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and
20 railway tracks, and on paths and squares with or without tree plantings. Equally, the
active compounds according to the invention can be employed for the control of 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
25 fields, in lawns, turf and pasture-land, and for the selective control of weeds in annual
crops.
The compounds of the formula (I) according to the invention have strong herbicidal
activity and a broad activity spectrum when used on the soil and on above-ground parts
30 of plants. To a certain extent, they are also suitable for the selective control of

Le A 33 917-Foreign Countries
monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledo¬nous crops, both pre-emergence and post-emergence.
The active compounds can be converted into the customary formulations, such as
5 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.
10 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 dispersants and/or foam formers.
If the extender used is water, it is also possible to employ, for example, organic
15 solvents as auxiliary solvents. Suitable liquid solvents are essentially the following:
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
20 glycol and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone,
methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and also water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals,
25 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
30 sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or
foam-forming agents are: for example nonionic and anionic emulsifiers, such as

Le A 33 917-Foreign Countries
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. 5
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, as well as natural phospholipids, such as cephalins and lecithins, and
synthetic phospholipids, can be used in the formulations. Other possible additives are
10 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,
15 copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
20 For the control of weeds, the active compounds according to the invention, as such or
in 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
25
acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromo-
30 butide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole,
caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben,

Le A 33 917-Foreign Countries
chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron,
cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-
(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl),
cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron,
5 cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,
dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl),
10 ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl),
fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil,
15 flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-methyl),
flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufo-sinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop-(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,
20 imazosulfuron, iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon,
isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, meto-sulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron,
25 naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,
oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,
30 pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate,
pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,

quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, sirhazihe, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thia-fluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
A mixture with other known active compounds, such as fungicides, .insecticides, acaricides, nematicides, bird repellents, 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 ias 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 relatively wide 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 present invention relates to substituted thienyl(amino)sulphonylures of the general formula (I)

in which
A represents nitrogen,
Q represents a single bond or represents NH,
R1 represents hydrogen, represents 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, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,
R2 represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylmino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy- substituted phenoxy, oxetanyloxy, furyloxy or tetahydrofuryloxy,
R3 represents hydrogen or represents optionally C1-C4alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms,
R4 represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6
carbon atoms, and

R5 represents hydrogen, represents optionally cyano-, halogen- or C1-C4 alkoxy-
substituted alkyl haying 1 to 6 carbon atoms, represents in each case optionally
halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms,
represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyi
or cycloalkylalkyl having in/each case 3 to 6 carbon atoms in the cycloalkyi groups and
optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally
cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or
tetrahydrofuryl.
25 ...The preparation and use of the active compounds according to the invention can be seen from the following examples below.

Le A 33 917-Foreign Countries
Preparation Examples:
Example 1
5 (Process (b))
0.75 g (2,9 mmol) of 2-phenoxycarbonylamino-4-methoxy-6-methyl-l,3,5-triazine is dissolved in 40 ml of acetonitrile and admixed successively with 0.75 g (3,2 mmol) of methyl 2-methyl-3-sulphamoyl-thiophene-4-carboxylate and 0.49 g (3.2 mmol) of
10 diazabicycloundecene (DBU). The reaction mixture is stirred at room temperature
(about 20°C) for 12 hours and then concentrated under water-pump vacuum. The residue is taken up in methylene chloride and the mixture is washed with 2N hydrochloric-acid and with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with
15 diethyl ether and the resulting crystalline product is isolated by filtration with
suction.
This gives 0.60 g (52% of theory) of N-(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-N"-(4-methoxycarbonyl-2-methyl-thien-3-yl-sulphonyl)-urea of melting point 195°C.
20

(Process (d))
Example 2

Le A 33 917-Foreign Countries

1.05 g (7.5 mmol) of chlorosulphonyl isocyanate are initially charged in 75 ml of
methylene chloride. After cooling to -10°C, a solution of 1.16 g (7.5 mmol) of
2-amino-4,6-dimethoxy-pyrimidine in 30 ml of methylene chloride is added
5 dropwise with stirring to this mixture, and the mixture is stirred at -10°C for 30
minutes. At 0°C, a solution of 1.28 g (7.5 mmol) of methyl 3-amino-2-methyl-
thiophene-4-carboxylate and 0.75 g (7.5 mmol) of triethylamine in 50 ml of
methylene chloride is then added dropwise, and the reaction mixture is stirred at
room temperature (about 20°C) for 12 hours. 100 ml of water in 100 ml of 2N
10 hydrochloric acid are then added and the organic phase is separated off, washed with
50 ml of water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum and the residue is crystallized from ethanol.
This gives 2.1 g (66% of theory) of N-(4,6-dimethoxy-pyrimidin-2-yl)-N"-
15 (4-methoxycarbonyl-2-methyl-thien-3-yl-amino-sulphonyl)-urea of melting point
174°C.
Analogously to Examples 1 and 2, and in accordance with the general description of
the preparation process according to the invention, it is also possible to prepare, for
20 example, the compounds of the general formula (I) listed in Table 1 below.

Le A 33 917-Foreign Countries

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

Ex. No. A Q R1 R2 R3 R4 R5 Melting point (°Q
3 CH NH OCH3 OCH3 H n-C3H7 C2H5 140
4 CH NH OCH3 OCH3 H i-C3H7 C2H5 154
5 CH NH OCH3 OCH3 H C2H5 CH3 195
6 CH - OCH3 OCH3 H CH3 CH3 194
Starting materials of the formula (V):
Example (V-l)

10

Step 1

At from 0°C to 5°C, a solution of 19.9 g (0.29 mol) of sodium nitrite in 60 ml of
water is added dropwise with stirring to a solution of 42.7 g (0.25 mol) of methyl
15 3-amino-2-methyl-thiophene-4-carboxylate in 75 ml of 10% strength aqueous
hydrochloric acid. The reaction mixture is stirred at from 0°C to 5°C for 60 minutes. The excess of nitrite is subsequently destroyed using amidosulphonic acid. At from 0°C to 5°C, the mixture is then added dropwise with stirring to a solution of 35 g (0.55 mol) of sulphur dioxide in 300 ml of methylene chloride. After addition of

Le A 33 917-Foreign Countries
1.5 g of copper(I) chloride and 1.5 g of dodecyl-trimethylammonium bromide, the
reaction mixture is stirred at 40°C for 60 minutes and then at 20°C for 12 hours.
18 ml of 35% strength aqueous hydrochloric acid are then added, the mixture is
stirred at 20°C for 4 hours and the phases are then separated. The aqueous phase is
5 re-extracted with methylene chloride and the combined organic phases are washed
with water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water-pump vacuum and the residue is crystallized from hexane.
This gives 51.7 g (81% of theory) of 4-methoxycarbonyl-2-methyl-thiophene-3-
10 sulphonyl chloride.
Step 2

15 A mixture of 45 g (177 mmol) of 4-methoxycarbonyl-2-methyl-thiophene-3-
sulphonyl chloride, 34 g (354 mmol) of ammonium carbonate and 400 ml of methylene chloride is stirred at room temperature (about 20°C) for 12 hours. The mixture is filtered and the solvent is distilled off from the filtrate under water-pump vacuum, the residue is digested with diethyl ether and the crystalline product is
20 isolated by filtration with suction.
This gives 21.5 g (52% of theory) of 4-methoxycarbonyl-2-methyl-thiophene-3-sulphonamide.

Le A 33 917-Foreign Countries
-Use Examples: Example A
5 Pre-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
10 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.
15 Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is
sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
20
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote: 25
0 % = no effect (like untreated control) 100% = total destruction
In this test, for example, the compounds of Preparation Examples 1, 2, 3, 4, 5 and 6
30 show very strong activity against weeds, and some of them are tolerated well by crop
plants, such as, for example, cotton, maize and soya.

Table Al: Pre-emergence test/greenhouse

r
a>
>
-J
I
o
TO
P
n
o
c
3
CO Icn

Table A2: Pre-emergence test/greenhouse

Table A3: Pre-emergence test/greenhouse

Table A4: Pre-emergence test/greenhouse

Table A5: Pre-emergence test/greenhouse

Table A6: Pre-emergence test/greenhouse

Le A 33 917-Foreign Countries
Example B
Post-emergence test
5 Solvent: 5 parts by weight of acetone
Emulsifier. 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, one part by weight of active
compound is mixed with the stated amount of solvent, the stated amount of
10 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 preparation of active
compound such that the particular amounts of active compound desired are applied
15 per unit area. The concentration of the spray liquor is chosen so that the particular
amounts of active compound desired are applied in 1000 1 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. 20
The figures denote:
0 % = no effect (like untreated control)
100% = total destruction 25
In this test, for example, the compounds of Preparation Examples 1, 2, 5 and 6 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, barley and wheat.

Table Bl: Post-emergence test/greenhouse

r
CD
-J 1
o
D
n
o
c
3
a>
en

Table B2: Post-emergence test/greenhouse

Table B3: Post-emergence test/greenhouse

Table B4: Post-emergence test/greenhouse

WE CLAIM:
Substituted thienyl(amino)sulphonylureas of the general formula (I)

in which
A represents nitrogen,
Q represents a single bond or represents NH,
R1 represents hydrogen, represents 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, or represents in each case optionally cyano-, halogen, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,
R2 represents hydrogen, represents halogen, represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylmino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy- substituted phenoxy, oxetanyloxy, furyloxy or tetahydrofuryloxy,

R3 represents hydrogen or represents optionally C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms,
R4 represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, and
R5 represents hydrogen, represents optionally cyano-, halogen- or C1-C4 alkoxy-substituted alkyl haying 1 to 6 carbon atoms, represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally cyano-, halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl.
2. Substituted thienyl(amino)sulphonylureas as claimed in claim 1, wherein
R1 represents hydrogen, fluorine, chlorine, bromine, iodine, or represents 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,
R2 represents fluorine, chlorine, bromine, or represents 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,

R3 represents hydrogen or represents in each case optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl,
R4 represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, and
R5 represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
3. Substituted thienyl(arnino)sulphonylureas as claimed in claim 1, wherein
R1 represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, or represents dimethylaminOj
R2 represents fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy , ethoxy, methylthio, ethylthio, methylamino or ethylamino, or represents dimethylamino,
R3 represents hydrogen or methyl,

R4 represents in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n-or i-propyl, and
R5 represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-siibstituted methyl, ethyl, n-or i-propyl, or represents in each ease optionally fluorine- or chlorine-substituted propenyl or propinyl.
4. 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 as
claimed in any one of claim 1 to 4.
5. Process for preparing compounds as claimed in any of claims 1 to 4,
wherein
(a) aminoazines of the general formula (II)

in which
A, R1 and R2 are each as defined in any of claims 1 to 3
are reacted with thienyl(amino)sulphonyl isocyanates of the general formula (III)

in which
Q, R4 and R5 are each as defined in any of claims 1 to 3, in the presence of a reaction auxiliary, of the kind such as herein described and in the presence of a diluent, of the kind such as herein described, wherein the process is carried out under atmospheric pressure and at temperatures between -20°C and +150°C.
6. Process for preparing compounds as claimed in any of claim 1 to 4 wherein, substituted aminoazines of the general formula (IV)

in which
A, R1 and R2 are each as defined in any of claims 1 to 3,
Z represents halogen, alkoxy or aryloxy and
R has the meaning given for R3 in any of claims 1 to 3 represents the grouping -C(OJ-Z,
are reacted with thiophene derivatives of the general formula (V)

in which
Q, R4 and R5 are each as defined in any of claims 1 to 3,
in the presence of a reaction auxiliary, of the kind such as herein described
and in the presence of a diluent, of the kind such as herein described, wherein
the process is carried out under atmospheric pressure and at temperatures
between -20°C and +1500C.
7. Herbicidal composition, wherein it comprises a compound as claimed in any of claims 1 to 5 between 0.1 and 95% by weight and customary extenders and/or surfactants, of the kind such as herein described.
8. Compounds of the general formula I substantially as herein described with reference to the forgoing examples.
9. Herbicidal composition substantially as herein described with reference to the foregoing examples.
Dated this on July 10, 2000

(DR. ANUSHRI GUPTA)
OF REMFRY & SAGAR
ATTORNEY FOR THE APPLICANTS

Documents:

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Patent Number

221178

Indian Patent Application Number

640/MUM/2000

PG Journal Number

35/2008

Publication Date

29-Aug-2008

Grant Date

18-Jun-2008

Date of Filing

10-Jul-2000

Name of Patentee

BAYER AKTIENGESELLSCHAFT

Applicant Address

D-51368 Leverkusen

Inventors:

#	Inventor's Name	Inventor's Address
1	MARK-WILHELM DREWES	Goethestr. 38, 40764 Langenfeld
2	PETER DIETER FEUCHT	Ackerweg 9, 40789 Monheim
3	ROLF PONTZEN	Am Kloster 69, 42799 Leichlingen
4	ERNEST-RUDOLF F. GESTING	Trillser Graben 4, 40699 Erkrath,
5	JOACHIM KULTH	Virneburgstr.69, 40764 Langenfeld
6	KLAUS-HELMUT MULLER	Solfstr.19, 40593 Dusseldorf

PCT International Classification Number

C07D409/12

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	19937118.0	1999-08-06	Germany