MXPA99005164A - Thienylsulfonylamino(thio)carbonyl compounds - Google Patents

Abstract

This invention concerns new thienylsufonylamino(thio)carbonyl compounds of formula (I) in which Q stands for oxygen of sulfur, R1 stands for cyano, halogen or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, optionally substituted in each case by cyno, halogen or C1-C14 alkoxy and having up to 6 carbon atoms, R2 stands for cyano, halogen or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, optionally substituted in each case by cyano, halogen or C1-C14 alkoxy and having up to 6 carbon atoms, and R3 stands for in each case optionally substituted heterocyclyle with 5 ring members of which at least one stands for oxygen, sulfur or nitrogen and one to three more stand for nitrogen. The invention also relates to salts of compounds of formula (I), processes, and new intermediate products for producing these new compounds, and their use as herbicides.

Description

- i - T-EE COMPOUNDS ILSULFOJILAMINO (UNCLE) CARBO IL / 3 Field of the invention. The invention relates to novel thienylsulfo-nylamino (thio) carbonyl compounds, various processes and new intermediates for their preparation as well as their use as herbicides. Description of the prior art. It is already known that certain sulfonylaminocarbo-nyl-co-acids exhibit herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). However, the effect of these compounds is not satisfactory on all occasions. Detailed description of the invention. The new thienylsulfo-nylamino (thio) carbonyl compounds of the general formula (I) have now been found, wherein Q means oxygen or sulfur, R1 means cyano, halogen or means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy with REF .: 30262- respectively up to 6 carbon atoms, substituted respectively by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means cyano, halogen or means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, with respectively up to 6 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and R3 means heterocyclyl, respectively substituted if appropriate, with 5 members in the ring, meaning at least one of them, oxygen, sulfur or nitrogen and can mean 1 to 3 more nitrogen, as well as the salts of the compounds of the formula (I) ). The new thienylsulfonylamino (-thio) carbonyl-compounds of the general formula (I) are obtained, if (a) sulphonamides of the general formula (II) are reacted wherein R1 and R2 have the meaning indicated above, with (thio) carboxylic acid derivatives of the general formula (III) .X. (H1) Z '"in which Q and R3 have the meaning indicated above and Z means halogen, alkoxy, aryloxy or arylalkoxy, optionally in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (b) sulfonyliso (thio) cyanates of the general formula (IV) are reacted wherein Q, R1 and R2 have the meaning indicated above, with heterocycles of the general formula (V) H-R3"1 (V) wherein > 3-l stands for heterocyclyl, optionally substituted, with 5 members in the ring, meaning at least one of them> NH, if appropriate in the presence of an auxiliary agent of the reaction and optionally in the presence of a diluent, or if (c) sulphonyl chlorides are reacted from the - general mule (VI) wherein R1 and R2 have the meaning indicated above, with heterocycles of the general formula (V) H-R3"1 (V) in which R3-1 has the meaning previously indicated in (b), with (thio) cyanates of the general formula (VII) QCN (VII) in which Q has the meaning indicated above and M means a metallic equivalent, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or if (d) sulphonyl chlorides of the general formula (VI) are reacted wherein R1 and R2 have the meaning indicated above, with (thio) carboxylic acid amides of the general formula (VIII) wherein Q and R3 have the meaning indicated in the case of formula (I), if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (e) they are reacted Sulfonylamino (thio) carbonyl-compounds of the general formula (IX) wherein Q, R1 and R2 have the meaning indicated above and Z means halogen, alkoxy, aryloxy or arylalkoxy, with heterocycles of the general formula (V) H-R3"1 (V) in which R3_1 has the meaning indicated above in (b), if appropriate, in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, and, if appropriate, the compounds obtained according to the procedures (a), (b), (c), (d) and (e) are transformed into sails according to usual methods. The processes (b), (c) and (e) are naturally suitable only for obtaining those compounds of the formula (I) in which R3 means R3-1. The novel thienylsulfonylamino (thio) carbonyl compounds of the general formula (I) are characterized by a potent herbicidal activity. The subject of the invention are preferably compounds of the formula (I), in which Q is oxygen or sulfur, R 1 is cyano, halogen, means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, halogen, or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 2 to 4 carbon atoms or alkynyl with 2 to 4 carbon atoms substituted, if appropriate, by cyano or by halogen, means alkoxy with 1 to 4 carbon atoms optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means alkenyloxy with 2 to 4 carbon atoms or alkynyloxy with 3 to 4 carbon atoms substituted, respectively, by cyano or Halogen, R 2 means cyano, halogen, means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen, or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 2 to 4 carbon atoms or alkynyl with 2 to 4 carbon atoms substituted, where appropriate, by cyano or by halogen, means alkoxy with 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means alkenyloxy with 2 to 4 carbon atoms; carbon or alkynyloxy atoms with 3 to 4 carbon atoms substituted, where appropriate, by cyano or halogen, and R 3 means heterocyclyl, respectively substituted, if appropriate, of the following formulas where Q1, Q2 and Q3 respectively mean oxygen or sulfur, and R4 is hydrogen, hydroxy, amino, cyano, means alkylidenamino having 2 to 10 carbon atoms, meaning alkyl having 1 to 6 carbon atoms, optionally substituted with fluorine , by chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylcarbonyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms, means alkenyl with 2 to 6 carbon or alkynyl atoms with 2 to 6 carbon atoms substituted, if appropriate, by fluorine, chlorine and / or bromine, means alkoxy with 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or alkyl-carbonylamino with 1 to 6 carbon atoms substituted respectively by fluorine, chlorine, bromine, cyano, alkoxy with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms means alkenyloxy with 3 to 6 carbon atoms, means di- (a alkyl with 1 to 4 carbon atoms) -amino, means cycloalkyl with 3 to 6 carbon atoms, cycloalkylamino with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms substituted respectively optionally fluorine, chlorine, bromine, cyano and / or alkyl having 1 to 4 carbon atoms, or phenyl or phenyl-alkylaryl having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine , by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl and / or by alkoxy with 1 to 4 carbon atoms, ignites hydrogen, hydroxy, mercapto, amino, cyano, fluorine , chlorine, bromine, iodine, means alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine by chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkyl-carbonyl with 1 to 4 atoms of carbon or by alkoxy-carbonyl with 1 to 4 carbon atoms, means alkenyl with 2 to 6 carbon or alkynyl atoms having 2 to 6 carbon atoms substituted, if appropriate, by fluorine, chlorine and / or bromine, means alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or alkylcarbonylamino with 1 to 6 carbon atoms, optionally substituted, if appropriate, by fluorine, chlorine, cyano, alkoxy with 1 to 4 carbon atoms, or by alkoxy carbonyl with 1 to 4 carbon atoms means alkenyloxy with 3 to 6 carbon atoms, alkynyloxy with 3 to 6 carbon atoms, alkenylthio with 3 to 6 carbon atoms, alkynylthio with 3 to 6 carbon atoms, alkenylamino with 3 6 carbon atoms or alkynylamino with 3 to 6 carbon atoms, means di- (alkyl having 1 to 4 carbon atoms) -amino, means aziridino, pyrrolidino, piperidino or morpholino, respectively substituted, if appropriate, by methyl and / or ethyl , means cycloalkyl with 3 to 7 carbon atoms, C5-C6alkalkenyl, cycloalkyloxy with 3 to 6 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms, cycloalkylane with 3 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms- alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms-alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms-alkylthio with 1 to 4 carbon atoms or cycloalkyl with 3 carbon atoms; at 6 carbon atoms-alkylamino having 1 to 4 carbon atoms, optionally substituted, respectively, by fluorine, chlorine, bromine, cyano and / or alkyl having 1 to 4 carbon atoms, or means phenyl, phenyl- alkyl with 1 to 4 carbon atoms, phenoxy, phenyl-alkoxy with 1 to 4 carbon atoms, phenylthio, phenyl-alkylthio with 1 to 4 carbon atoms, phenylamino or phenyl-alkylamino with 1 to 4 carbon atoms substituted respectively, where appropriate, fluorine, chlorine, bromine, cyano, nitro, alkyl with 1 to 4 atoms of carbon, by trifluoromethyl, by alkoxy with 1 to 4 carbon atoms and / or by alkoxy-carbonyl with 1 to 4 carbon atoms, and R5 together, mean alkanediyl, if any branched, with 3 to 11 carbon atoms, further R6, R7 and R8 are the same or different and mean hydrogen, cyano, fluorine, chlorine, bromine, or mean alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyl or alkylsulfonyl with respectively up to 6 carbon atoms, each optionally substituted by fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms - or not meaning cycloalkyl with 3 to 6 carbon atoms, optionally substituted by cyano, fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms. The object of the invention is also preferably sodium, potassium, magnesium, calcium, ammonium, alkyl-ammonium salts with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms). carbon) -ammonium, tri- (C1-C4 alkyl) -ammonium, tetra- (C1-C4 alkyl) -ammonium, tri- (C1-C4 alkyl) sulfonium, cycloalkyl ammonium with 5 or 6 carbon atoms and di- (C 1 -C 2 alkyl) -benzyl ammonium of the compounds of the formula (I), wherein Q, R 1, R 2 and R3 have the previously given meaning preferentially.

The subject of the invention are especially compounds of the formula (I), in which Q is oxygen or sulfur, R 1 is cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i- or s-butyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propinyl or butynyl substituted, where appropriate, by cyano, by fluorine or by chlorine, respectively methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means propenyloxy, butenyloxy, propynyloxy or butynyloxy substituted, where appropriate, by cyano, fluorine or chlorine, R2 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted respectively in case given by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propinyl or bu tinyl substituted, where appropriate, by cyano, fluorine or chlorine, means methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted, where appropriate, by cyano, by fluorine, by chloro, methoxy or ethoxy, or means propenyloxy, butenyloxy, pro-phenyloxy or butynyloxy substituted, where appropriate, by cyano, fluorine or chlorine, and R3 means substituted heterocyclyl, respectively, of the following formulas where Q1, Q2 and Q3 respectively mean oxygen or sulfur, and R4 is hydrogen, hydroxy, amino, means methyl ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, respectively, by fluorine, chlorine, cyano, methoxy or ethoxy, means propenyl, butenyl, propynyl or butynyl substituted, if appropriate, by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, n - i-, s- or t-butoxy, methylamino, ethylamino, n- or i- propylamino, n-, i-, s- or t-butylamino substituted, where appropriate, by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, means propenyloxy, or butenyloxy, means dimethylamino or diethylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclo-pentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted respectively where appropriate by fluorine, by chlorine, by methyl or and / or by ethyl, or means phenol or benzyl substituted, where appropriate, by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy, hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, means ethenyl, propenyl, butenyl , propynyl or butynyl substituted, where appropriate, by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, n-, i- s- or t-butoxy, methylthio, ethylthio, n- or -propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino respectively substituted, if appropriate by fluorine, by chlorine, by cyano, methoxy or ethoxy, means propenyloxy, butenyloxy propynyloxy, butynyloxy, propenylthio, propadienylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propylamino or butyne. ilamino, means dimethylamino, diethylamino or dipropylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylthiamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino substituted, where appropriate, by fluorine, by chlorine, by methyl and / or ethyl, or by phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino substituted, where appropriate, by fluorine, chlorine, methyl, trifluoromethyl, methoxy and / or methoxycarbonyl, or R4 and R5 together mean alkanediyl, optionally branched, with 3 to 11 carbon atoms , further R6, R7 and R8 are the same or different and denote hydrogen, cyano, fluorine, chlorine, bromine, or mean methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , propenyl, butenyl, propynyl, butenyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, propethylthio, butenylthio, propinylthio, butylthio, methylsulph inyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl. A very particularly preferred group of compounds according to the invention are the compounds of the formula (1), in which Q is oxygen p sulfur, R 1 is methyl, ethyl, n- or i-propyl, R 2 is methyl, ethyl, n- or i-propyl and R3 means triazolinyl substituted, if any, of the following formula, N A N- FT N R3 Q 1 is oxygen or sulfur, and R 4 is methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine, chlorine, methoxy or ethoxy, means propenyl or propynyl substituted respectively by fluorine or by chloro means methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, means propenyloxy, means dimethylamino or means cyclo-propyl, means chloro or bromo, means methyl, ethyl, non-i-propyl , n-, i-, s- or t-butyl substituted respectively by fluorine, chlorine, cyano, methoxy or ethoxy, means ethenyl, pro-penyl, butenyl, propynyl or butynyl substituted, respectively, if appropriate by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, ni-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino respectively substituted, if appropriate, by fluorine , by chlorine, by cyano, by methoxy or by ethoxy, means propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, pro-padienylthio, butenylthio, propynylthio, butynylthio, pro-penylamino, butenylamino, propynylamino, or butynylamino, means dimethylamino, diethylamino or dipropylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopro-pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopenthylamino, cyclohexylamino, cyclopropyl ethyl, tilmetilo cyclobutyl, cyclopentylmethyl, cyclohexylmethyl, cyclo- propilmetoxi, cyclobutylmethoxy, cyclopentylmethoxy, ci- clohexilmetoxi, cyclopropylmethylthio, ciclobutilmetil- thio, ciclopentilmetiltio, ciclohexilmetiltio, cyclo- propylmethylamino, cyclobutylmethylamino, cyclopentylmethyl or cyclohexylmethylamino ino linden in each case optionally substituted by fluorine, by chlorine, by methyl and / or by ethyl, or phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino respectively substituted, if appropriate, by fluorine, chlorine, methyl, trifluoromethyl, methoxy and / or ethoxycarbonyl, or R4 and R5 mean together alkanediyl, if appropriate branched, with 3 to 11 carbon atoms. The definitions of the residues indicated above in a general manner or in the preferred ranges are valid both for the final products of the formula (1) and also correspondingly for the starting materials or the intermediate products necessary respectively for the preparation. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated.

If, for example, 4-bromo-2-methyl-thiophene-3-sulfonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1, 2,4-triazole-3 are used -tiona, as starting products, the development of the reaction in the case of process (a) according to the invention can be schematized by means of the following formula scheme: If, for example, 4-chloro-2-ethyl-3-thienylsulfonyl isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one are used as starting products, the reaction can be schematized in the case of process (b) according to the invention by means of the following formula scheme: If they are used, for example, 4-ethyl-2-methoxy-thiophene-3-sulfochloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and the potassium cyanate as starting compounds, the development of the reaction in the case of process (c) according to the invention can be schematized by means of the following formula scheme: If, for example, 4-cyano-2-iso-propyl-thiophene-3-sulfochloride and 5-methyl-1,2,4-oxadia-zol-3-carboxamide are used as starting compounds, the development of the reaction in the case of process (d) according to the invention by means of the following formula scheme: If, for example, N- (4-fluoro-2-trifluoromethyl-thiophen-3-ylsulfonyl) -O-methyl-urethane and 4-methyl-5-methylthio-2,4-dihydro-3H are used -l, 2, 4-triazol-3-one as starting compounds, the development of the reaction in the case of process (e) according to the invention can be schematized by means of the following formula scheme: S02-NH-COOCH3 N = J ^ _-? F S02 ^ N ^ NN N "CH, SCH, H N = SCH, The sulfonamides to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R 1 and R 2 preferably have, or in particular, that meaning which has already been mentioned above in a preferred manner or, more particularly, for R 1 and R 2 in the description of the compounds of the formula (I) according to invention. The starting materials of the formula (II) are not yet known in the literature; as new products they are also an object of the present application. The novel sulfonamides of the formula (II) are obtained if sulfonyl chlorides of the formula (VI) are reacted wherein R1 and R2 have the meaning indicated above, with ammonia, if appropriate in the presence of a diluent, such as for example water, at temperatures between 0 ° C and 50 ° C (see the preparation examples). The sulfonyl chlorides of the formula (VI) are also not known in the literature; as new products they are also an object of the present application. The novel sulfochlorides of the formula (VI) are obtained if corresponding amino-compounds of the general formula (X) are reacted wherein R1 and R2 have the meaning indicated above, with an alkali metal nitrite, such as for example sodium nitrite, in the presence of hydrochloric acid at temperatures between -10 ° C and + 10 ° C and the solution of the The diazonium salt thus obtained is reacted with sulfur dioxide in the presence of a diluent, such as, for example, dichloromethane, 1,2-dichloroethane or acetic acid, and in the presence of a catalyst, such as, for example, Cuprous chloride (I) and / or cupric chloride (II), at temperatures between -10 ° C and + 50 ° C (see the preparation examples).

The amino compounds necessary as starting materials of the formula (X) are known and / or can be prepared according to processes known per se (see DE 33 03 388). The derivatives of the (thio) carboxylic acids to be used as starting materials furthermore in the process (a) according to the invention for the preparation of the compounds of the formula (I), are generally defined by means of the formula (III) ). In the formula (III), Q and R3 preferably have or especially that meaning which has already been indicated preferably or particularly preferably for Q and R3 in the description of the compounds of the formula (I) according to the invention; preferably Z means fluorine, chlorine, bromine, alkoxy with 1 to 4 carbon atoms, phenoxy or benzyloxy, especially chlorine, methoxy, ethoxy or phenoxy. The starting materials of the formula (III) are known and / or can be prepared by processes known per se (see EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266). The sulfonyl iso (thio) cyanates to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula '(IV) . In the formula (IV), Q, R1 and R2 preferably have or especially that meaning which has already been indicated above, preferably or especially preferably for Q, R1 and R2 in the description of the compounds of the formula ( I) according to the invention. The iso (thio) cyanates of sulfonyl of the formula (IV) are not yet known from the literature; these constitute, as new products, also an object of the present application. The new iso (thio) cyanates of the sulfonyl of the formula (IV) are obtained if sulfonamides of the general formula (II) are converted prior to phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as, for example, butyl isocyanate, optionally in the presence of a reaction aid, such as, for example, diazabicyclo [2, 2, 2] octane, and in the presence of a diluent, such as, for example, toluene, xylene or chlorobenzene, temperatures between 80 ° C and 150 ° C and, after completion of the reaction, the volatile components are removed by distillation under reduced pressure (see the preparation examples). The heterocycles, to be used as starting materials in processes (b), (c) and (e) according to the invention, are generally defined by means of formula (V). In the formula (V), R3"1 preferably means thiazolinyl, if substituted, of the following formula, Q1 ^ N ~ N: R5 where Q1 signifies oxygen or sulfur and the residues R4 and R5 preferably have or especially those meanings which have already been indicated above, preferably or particularly preferably for R 4 or for R 5 in the description of the compounds of the formula (I) according to the invention The starting materials of the formula (V) are known and or can be prepared according to known processes (see EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266) The sulfonyl chlorides to be used as starting materials in processes (c) and ( d) according to the invention, for the preparation of the compounds of the formula (I), they are generally defined by the formula (VI). In the formula (VI), R1 and R2 preferably have or especially that meaning which It has previously been indicated in a preferred manner or, more preferably, for R1 and R2 in the description of the compounds of the formula (I) according to the invention. The sulfonyl chlorides of the formula (VI) are not yet known from the literature; as new products they are also an object of the present application and can be prepared as described above. The amides of the (thio) carboxylic acids to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (VIII) . In the formula (VIII), Q and R3 preferably have or especially that meaning which has been previously indicated in a preferred manner or in a particularly preferred manner for Q and R3 in the description of the compounds of the formula (I) according to the invention. The starting materials of the formula (VIII) are known and / or can be prepared according to processes known per se (cf. EP 459244). The sulfonylamino (thio) carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (IX). In the formula (IX), Q, R1 and R2 preferably have or especially that meaning which has already been indicated above, preferably or especially preferably for Q, R1 and R2 in the description of the compounds of the invention. formula (I) according to the invention; preferably Z means fluorine, chlorine, bromine, alkoxy with 1 to 4 carbon atoms, phenoxy or benzyloxy, especially chlorine, methoxy, ethoxy or phenoxy. The starting materials of the formula (IX) are known and / or can be prepared according to methods known per se. The processes (a), (b), (c), (d) and (e) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents are practically all inert organic solvents in this case. These preferably include halogenated aliphatic and aromatic hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, to-luene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichloro-benzene; ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl-ethyl-, methyl-isopropyl- and methyl-isobutyl-ketone; esters such as methyl acetate and ethyl acetate; nitriles such as, for example, acetonitrile and propionitrile; amides, such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethylsulfoxide, tetramethylenesulphonane and hexamethylphosphorotriamide. All the acid-binding agents which can be used in such reactions can be used as acid-binding agents or as acid acceptors in processes (a), (b), (c), (d) and (e) according to the invention. Preference will be given to alkali metal hydroxides such as, for example, sodium and potassium hydroxide, alkaline earth metal hydroxide, such as, for example, calcium hydroxide, carbonates and alcoholates of alkali metals such as sodium and potassium carbonate, tere. sodium and potassium butylate, in addition basic nitrogenous compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyl-diisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine , 2-methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl- pyridine, 1,5-diazabicyclo [4, 3,0] -non-5-ene (DBN), 1,8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU) and 1,4-diazabicyclo [2,2,2] -octane (DABCO). The reaction temperatures in the processes (a), (b), (c), (d) and (e) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and + 100 ° C. The processes according to the invention (a), (b), (c), (d) and (e) are generally carried out under normal pressure. However, it is also possible to work under higher pressure or at a lower pressure. To carry out the procedures (a), (b), (c), (d) and (e) according to the invention the starting materials required in each case are generally used in approximately equimolar quantities. However, it is also possible to use one of the components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor and the reaction mixture is stirred for several hours at the temperature required in each case. The preparation is carried out in processes (a), (b), (c), (d) and (e) according to the invention respectively according to customary methods (see the preparation examples). Compounds can be prepared, if appropriate, from the compounds according to the invention of the general formula (I). Such salts are obtained in a simple manner according to the usual methods of salt formation, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tere. -buti1-methy1-ether or toluene, and addition of a suitable base. The salts can then be isolated, if necessary after prolonged stirring, by evaporation or by suction filtration. The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as agents for removing weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: Bad dicotyledonous herbs of the kinds; Sinapis Lepi-diu, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia , Lamium, Veronica, Abutilon, E ex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Cultures of dicotyledonous classes; Gossypium, Gly-cinema, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the kinds; Echino-chloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes; Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Sac-charum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. In the same way, compounds can be used to control weeds in permanent crops, for example in forestry, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, plantains, coffee, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in mono-annual crops. The compounds according to the invention of the formula (I), according to the invention, are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in onocotyledonous cultures both in the pre-emergence procedure and in the post-emergence process. The active products can be transformed into the usual formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as micro-encapsulated materials polymers. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants. santes and / or means generating foam.

When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed , aluminum oxide and silicates, as solid excipients for granulates come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice foot, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; suitable emulsifiers and / or foam generators are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfone-tos, as well as albumin hydrolysates.; Suitable dispersants are, for example, sulfitic leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids can be used in the formulations. . Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations also for combating weeds in admixture with herbicides, ready-to-use preparations or tank mixtures being possible. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydi (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl) ), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetami-de, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu-rum (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransu-lam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfa-muron, Cycloxydim, Cyhalofop (-butyl), 2,4-D , 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-meti-lo), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, diquat, dithiopyr, diuron, dymron, EPTC, Es-procarb, ethalfluralin, ethametsulfuron (-methyl), Ethofu-mesate, Ethoxyfen, etobenzanid, Fenoxaprop- (ethyl), Fram-prop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (me-linden), flazasulfuron, fluazifop (butyl), Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, Fluome-turon, fluorochloridone, fluoroglycofen (-ethyl), Flupo-xam , Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flur-primidol, Flurtamone, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl) - Hexazinone, Imazamethabenz (-methyl), Imazamet-hapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazo-sulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Metha-benzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metsulfuron (-methyl), Metribuzin, Molinate, Monoli Nuron, Naproanilide, Napropamide, Nebu-ron, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phen e-dipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide , Prosulfocarb, Prosulfuron, Pyrazolate, Pyra-zosulfuron (-ethyl), pyrazoxyfen, pyributicarb, Pyridate, pyrithiobac (-sodium), Quinchlorac, quinmerac, Quizalofop- (ethyl), quizalofop (-P-tefuryl), rimsulfuron, Sethoxy-dim , Simazine, simetryn, sulcotrione, Sulfentrazone, Sul-fometuron (-methyl), Sulfosate, tebutam, Tebuthiuron, Ter-buthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thia-zopyr, hidiazimin, thifensulfuron (-methyl), hiobencarb, tiocarbazil, tralkoxydim , Triallate, Triasulfuron, Tribe-nuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Tri-flusulfuron. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground. The active compounds can be used as such, in the form of their formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plans. They can also be incorporated into the soil before sowing. The quantities of active product used can vary within a wide range. These depend fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active substances according to the invention is apparent from the following examples: Preparation examples. Example 1 (Procedure (a)). They are added to a solution of 1.6 g (6.4 mmoles) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1, 2,4-triazole-3-. ona, in 30 ml of acetonitrile, successively, 1.3 g (6.8 mmoles) of 2,4-dimethyl-thiophene-3-sulfonamide and 1.1 g (7 mmoles) of 1,8-diazabicyclo- [5, 4, 0] -un-dec-7-ene (DBU). The reaction mixture is stirred for about 15 hours at room temperature (approximately 20 ° C) and then concentrated by evaporation under vacuum of the water tube. The residue is then taken up in methylene chloride, washed with IN hydrochloric acid and then with water. The organic phase is dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump and the residue is recrystallized from isopropanol. 1.1 g (50% of theory) of 5-ethoxy-4-methyl-2- (2,4-dimethyl-thien-3-yl-sulfonylaminocarbonyl) -2,4-dihydro-3H- are obtained 1,2,4-triazol-3-one with a melting point of 158 ° C. Example 2 (Procedure (d)) 2.0 g (36 mmol) of potassium hydroxide powder, at 20 ° C up to 35 ° C maximum, are added to a solution of 1.52 g (12.0 mmol) of 5- methyl-1,2,4-oxadiazole-3-carboxamide in 150 ml of dioxane. After 30 minutes, about 50 ml of dioxane is distilled off under vacuum from the water tube at 30 ° C to 35 ° C. The mixture is then combined, in portions, with 2.65 g (12.6 mmol) of 2,4-dimethyl-thiophene-3-sulfochloride and the reaction mixture is stirred for approximately 12 hours at room temperature (20). ° C approximately). It is then concentrated by evaporation under vacuum of the water pump, the residue is taken up in water and acidified with 2N hydrochloric acid. It is then extracted twice with 100 ml of methylene chloride each time. The combined organic solutions are washed with water, dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump and the residue is recrystallized from ethanol. 0.7 g (19% of theory) of N- (2,4-dimethyl-thien-3-ylsulfonyl) -5-methyl-1,2,4-oxadiazole-3-carboxamide are obtained with a dot of fusion of 164 ° C. In a manner analogous to that of Examples 1 and 2 and according to the general description of the preparation processes according to the invention, for example, the form-mule (I) compounds set out in Table 1 below can also be prepared.

Table 1; Examples of compounds of the formula (I) bla 1 Continuation) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Starting products of the formula (II); Example (Il-li.

A mixture of 6.0 g (29 mmol) of 2,4-dimethyl-thiophene-3-sulfochloride and 30 ml of 25% strength aqueous ammonia solution is stirred for 12 hours at room temperature, about 20 ° C. . The crystalline product formed in this case is then isolated by suction filtration. 4.3 g (80% of theory) of 2,4-dimethyl-thiophene-3-sulfonamide having a melting point of 135 ° C are obtained. Starting products of the formula (IV); Example (1V-1).

A mixture consisting of 19.1 g (100 mmol) of 2,4-dimethyl-thiophene-3-sulfone-mide, 10.0 g (100 mmol) of butyl isocyanate and 100 ml of chloroform is heated to boiling. Phosgene is passed through the mixture at reflux temperature for 4 hours. It is then concentrated by evaporation under vacuum of the water pump and the residue is subjected to a vacuum distillation of the oil pump. 10.3 g (47% of theory) of 2,4-dimethyl-thien-3-yl-sulfonyl isocyanate are obtained with a boiling range of 135 ° C to 140 ° C (at 1 mbar). Starting products of the formula (VI); Example (Vi-D.

A solution of 13.9 g (109 mmol) of 3-amino-2,4-dimethyl-thiophene in 30 ml of 10% hydrochloric acid is cooled to 0 ° C and 50 ml of concentrated hydrochloric acid are combined. Then it is added drop by drop, under cooling at 0 ° C, at -5 ° C, under stirring, a solution of 8.6 g (125-mmoles) of sodium nitrite in 22 ml of water. The reaction mixture is stirred for approximately 1 hour at 0 ° C to -5 ° C. The excess sodium nitrite is then destroyed with amidosulfonic acid. The diazonium salt solution obtained in this way is added, dropwise, at about 15 ° C, a solution of 12 g of sulfur dioxide in 100 ml of 1,2-dichloroethane. Then 600 mg of cuprous chloride (I) and 600 mg of dodecyltrimethylammonium bromide are added and the reaction mixture is stirred for approximately 1 hour at about 40 ° C and for a further 12 hours at room temperature (approximately at 20 ° C). After addition of 6 g of 30% solution of hydrogen peroxide, the mixture is stirred for another 30 minutes. The organic phase is then separated, washed twice with water, dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested in petroleum ether and the crystalline product formed is isolated by suction filtration. 9.6 g (42% of theory) of 2,4-dimethyl-thiophene-3-sulfochloride with a melting point of 79 ° C are obtained. Respectively, analogously to examples (II-1), (IV-1) and (VI-1), it was also possible to prepare, for example, the compounds of formulas (II), (IV) and (VI) indicated in Table 2 below: Table 2; Examples of compounds of the formulas (II), (IV) and (VI) [ie the residues R1 and R2 are valid for each of these formulas]; Q means o or S.

Application examples; Example A. Pre-emergence trial. Solvent; 5 parts by weight of acetone. Emulsifier: 1 part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil. After approximately 24 hours, the soil is sprayed with the active product preparation. In this case, the quantity of water per unit area is suitably constant. The concentration of the preparation does not play any role, the sun being the fundamental amount of application of the active product per unit area. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control. They mean: 0% = no effect (same as untreated controls). 100% = total destruction.

In this test, for example, the compounds according to Preparation Examples 1, 3, 4, 5, 11 and 12 show a partially good compatibility with crop plants, such as, for example, corn and wheat, a potent efesto. against weeds (see table A). ai. "= active product (" active ingredient). Table A; Pre-sprout / greenhouse test Product Quantity Corn Bro- Cype- Lo- Se- Cheno- Matri- Sola-active used mus rus lium tarla podium caria mum according to ex. (g al / ha) of obtaining nfi O NH ? Jl 125 100 100 100 100 100 100 100 H3C C2HS (3) Table A; (Continued) Pre-sprout / greenhouse test Product Quantity Wheat Bro- Cype- Lo- Se- Cheno- Matri- Sola- active used mus rus lium taria podium caria mum according to ex. (g ai / ha) of obtaining na 100 95 100 100 100 100 100 0) Table A (Continued) Pre-sprout / greenhouse test Product Quantity Corn Wheat Bro- Cype- Lo- Se- Cheno- Ma- Sola- active used mus rus lium ta podium tri- mum according to j. (g ai / ha) ria caria of obtaining na (4) Table A (Continued) Pre-sprout / greenhouse test Product Quantity Bro- Cype- Lo- Seta- Cheno- Matri - Sola- active used mus rus lium ria podium caria according to ex. (g ai / ha) of obtaining ns 0 V j, H Y 125 100 100 100 100 95 100 95 H3C O - CH, (H) Table A (Continued) Pre-sprout / greenhouse test Active product Quantity Alope- Abuti- Amaran- Sina-Xan-vo according to ex. employed curus Ion thus obtaining thium pis (g ai / .ha) na ° ^ = J N 250 70 90 90 95 90 H, C O- "> -CH, (5) Y (12) Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. With the active product preparation, test plants are sprayed, having a height of 5-15 cm, so that the desired quantities of active compound per unit of surface are applied respec- tively. The concentration of the sprayable broths is chosen in such a way that the desired quantity in each case of active product is applied in 1,000 liters of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. Signifisan: 0% = no efesto (same as the untreated strings). 100% = total destrussión. In this test they show, for example, the somersaults according to the examples of obtention 6, 13 and 14, with a comparatively good compatibility with the sultivo plants, such as for example maize, a powerful efesto sontra the weeds (see Table B). Table B; Pre-sprout / greenhouse trial Produsto acti- Amount Corn Setaria Abuti- Amaran- Sina-vo according to e. employed Ion thus obtaining pis (g ai /. ha) na (6) (13) Table B (Continued) Pre-sprout / greenhouse test Product active- Amount Corn Setaria Abuti- Amaran- Sina-vo according to e. employed Ion thus obtaining pis (g ai / .ha) na (14) It is noted that in relation to this date, the best method conosido by the solisitant to bring to the prststisa the sitada invention, is the one that is slaro of the present dessripsión of the invention.

Claims (1)

CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. - 'Thienylsulphonylamino (thio) carbonyl compound of the general formula (I) characterized in that Q represents oxygen or sulfur, R1 signifies sia, halogen or signifisa alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy with respectively up to 6 sarbone atoms, respectively substituted in saso given by sian, by halogen or by alsoxi with 1 a 4 carbon atoms, R 2 signifisa sia, halogen or signifisa alkyl, alkenyl, alkynyl, alsoxi, alkenyloxy or alkynyloxy, are respec tively up to 6 atoms sarbono substituted resoplastily in saso given by cyano, by halogen or by alkoxy are 1 to 4 atoms of sarbono, and R3 signifisa heterosislilo, resinsively substituted in given saso, are 5 members in the ring, meaning at least one of them, oxygen, sulfur or nitrogen and being able to signify 1 to 3 more nitrogen, thus som salts of the compounds of the formula (I). 2. Compounds of the formula (I) according to claim 1, sarasterized because Q means oxygen or sulfur, R1 means sian, halogen, signifissa alkyl are 1 to 4 atoms of substituted sarbono in saso given by siane, by halogen, or by alkoxy with 1 to 4 carbon atoms, meaning alkenyl or 2 to 4 atoms of sarbono or alkynyl are 2 to 4 atoms of sarbono, substituted respectively in saso given by siao or by halogen, meaning alsoxi are 1 to 4 atoms of sarbono- not substituted in saso given by siano, by halogen or by alsoxi are 1 to 4 atoms of sarbono, or signifisa alkeniloxi are 2 to 4 atoms of sarbono or alkynyloxy are 3 to 4 atoms of sarbono resitually substituted in saso given by cyano or by Halogen, R 2 means cyano, halogen, means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen, or by alkoxy is 1 to 4 atoms of sarbon, meaning alkenyl or 2 to 4 atoms of sarbon or alkynyl are 2 to 4 sarbono atoms substituted respec- tively in saso given by siao or by halogen, signifisa alsoxi are 1 to 4 atoms of sarbono substituted in saso given by sian, by halogen or by alsoxi are 1 to 4 atoms of sarbon, or signifisa alkeniloxi are 2 to 4 atoms of sarbono or alkynyloxy are 3 to 4 carbon atoms substituted respectively in saso given by siao or by halogen, and R3 signifisa heterosislilo, resinsively substituted in given saso, of the following formulas where Q1 / Q2 and Q3 are resitantly oxygen or sulfur, and R4 is hydrogen, hydroxy, amino, siamino, alkylidene amino with 2 to 10 sarbono atoms, signifissa alkyl are 1 to 6 atoms of sarbono, optionally substituted by fluorine, chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylsarbonyl are 1 to 4 atoms of sarbon or by alkoxycarbonyl with 1 to 4 carbon atoms, meaning alkenyl with 2 to 6 carbon atoms. carbon or alkynyl are 2 to 6 sarbono atoms respecifically substituted in saso given by fluorine, by chlorine and / or by bromine, means alsoxi are 1 to 6 atoms of sarbon, alkylamino are 1 to 6 atoms of sarbon or alkyl-sarbonylamino are 1 to 6 sarbono atoms, which are respec- tively substituted in saso given by fluorine, by sloro, by bromine, by sian, by alsoxi are 1 to 4 atoms of sarbono or by alsoxi-sarbo-nile are 1 to 4 atoms of sarbono, signifisa alkeniloxi are 3 to 6 atoms of sarbon, signifisa di- (a alkyl are 1 to 4 atoms of sarbono) -amino, signifisa sisloalquilo are 3 to 6 atoms of sarbono, sisaloalkylamino are 3 to 6 atoms of sarbono or sisloalquilo are 3 to 6 atoms of sarbono-alkyl are 1 to 4 atoms of sarbono replaced respestivamente in saso given by fluorine, by sloro, by bromine, by sian and / or by alkyl are 1 to 4 atoms of sarbono, or signifisa phenyl or phenyl-al-chyl are 1 to 4 atoms of sarbono respectively replaced in saso given by fluorine , by sloro, by bromine, by cyano, by nitro, by alkyl with 1 to 4 atoms of sarbon, by trifluoromethyl and / or by alsoxi are 1 to 4 carbon atoms, means hydrogen, hydroxy, mersapto, amino, siamino, fluorine, sloro, bromine, iodine, signifisa alkyl are 1 to 6 atoms of sarbono substituted in saso given by fluorine by sloro, by bromine, by sian, by alsoxi are 1 to 4 atoms of sarbon, by alkyl-sarbonilo are 1 to 4 atoms of sarbono or by alsoxi-sarbonilo are 1 to 4 atoms of sarbono, signifisa alquenilo are 2 to 6 atoms of sarbono or alquinilo are 2 to 6 atoms of sarbono replaced respestivamente in saso given by fluorine, by sloro and / or by bromine, signifisa alsoxi they are 1 to 6 atoms of sarbono, alkylthio is 1 to 6 atoms of sarbono, al-quilamino are 1 to 6 atoms of sarbono or alquil-sarbo-nilamino are 1 to 6 atoms of sarbono respectively replaced in saso given by fluorine, by sloro , by sian, by alsoxi are 1 to 4 atoms of sarbon, or by alsoxi-sarbonilo are 1 to 4 atoms of sa rbono means alkenyloxy with 3 to 6 carbon atoms, alkynyloxy with 3 to 6 carbon atoms, alkenylthio with 3 to 6 carbon atoms, alkynylthio with 3 to 6 carbon atoms, alkenylamino with 3 to 6 carbon atoms or alkynylamino with 3 to 6 carbon atoms, means di- (alkyl with 1 to 4 atoms of sarbon) -amino, signifisa aziridino, pyrrolidino, piperidino or morpholino resinsively substituted in saso given by methyl and / or by ethyl, signifisa sisloalquilo are 3 to 7 sarbono atoms, sisloalkenyl are 5 to 6 atoms of sarbono, sisloalkyloxy are 3 to 6 atoms of sarbono, sislo-alkylthio are 3 to 6 atoms of sarbono, sisaloalquilami-no are 3 to 6 atoms of sarbono, sicloalquilo with 3 to 6 atoms carbon-alkyl with 1 to 4 carbon atoms, cisloalkyl are 3 to 6 atoms of sarbon-alsoxi are 1 to 4 atoms of sarbon, sisloalkyl are 3 to 6 atoms of sarbono-alkylthio are 1 to 4 atoms of sarbono or sisloalquilo are 3 to 6 atoms of sarbono-alkyl-amino are 1 to 4 sarbono atoms, which are respec- tively substituted in saso given by fluorine, by sloro, by bromine by cyano and / or by alkyl with 1 to 4 atoms of sarbon, or signifisa phenyl, phenyl-alkyl are 1 to 4 atoms of sarbon, phenoxy, phenyl-alsoxy are 1 to 4 atoms of sarbon, phenylthio, phenyl-alkylthio are 1 to 4 atoms of sarbon, phenyl-amino or phenyl-alkylamino are 1 to 4 atoms of sarbono respectively replaced by fluoro, by sloro, by bromo, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl, by alkoxy are 1 to 4 atoms of sarbon and / or by alsoxi-sarbonyl with 1 to 4 carbon atoms, or R4 and R5 signifisan they are alsanodiyl, in a given branched state, they are 3 to 11 atoms of sarbon, further R6, R7 and R8 are the same or different and are hydrogen, siane, fluorine, sloro, bromine, or they mean alkyl, alkenyl, alkynyl, alsoxi, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyl or alkylsulfonyl with respectively up to 6 carbon atoms, respectively substituted by fluorine, by slurry, by bromine or by arexy, are from 1 to 4 sarbon atoms or by cycloalkyl having 3 to 6 carbon atoms substituted by cyan, by fluorine, chlorine, bromine or alkyl are 1 to 4 atoms of sarbon, so that sodium salts, potassium salts, magnesium salts, salts of sodium, ammonium salts, and alkyl ammonium salts are 1 to 4 carbon atoms. sarbono, of di- (alkyl are 1 to 4 atoms of sarbon) -ammonium, of tri- (C1-C4 alkyl) -ammonium, of tetra- (C1-C4 alkyl) -ammonium, of tri- (alkyl are 1 to 4 atoms of sarbon) -sulfonium, of sisloalkyl-ammonium are 5 or 6 atoms of sarbon and of di- (alkyl are 1 to 2 atoms of sarbon) -bensil-ammonium of the atoms of the formula (I). 3.- Procuring for the obtention of thienyl-sulfonylamino (thio) carbonyl-compounds of the general formula (I) according to claim 1, sarasterized because (a) sulphonamides of the general formula (II) have been resuspended wherein R1 and R2 have the meaning previously undesired, are derives of saridic acid (thio) of the general formula (III) Q,? (lll) R "in which Q and R3 have the meaning previously unsubstantiated and Z signifies halogen, alsoxi, aryloxy or arylalkyloxy, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or because (b) sulfonyliso (thio) cyanates of the general formula (IV) are reacted wherein Q, R1 and R2 have the previously undeserved meaning, are heterosislos of the general formula (V) in which, 3-1 signifisa heterosislilo, in given substituted saso, are 5 members in the ring, meaning at least one of they > NH, if appropriate in the presence of an auxiliary agent of the reation and in saso given in the presence of a diluent, or because (s) sulphonyl slorides of the general formula (VI) (VI) have been reached in which R1 and R2 have the meaning previously unheard, are heterosislos of the general formula (V) H-R3"1 (V) in which R3-1 has the meaning previously indentured in (b), are (thio) metallized siatals of the general formula (VII) QCN (VII) in which Q has the meaning previously uninformed and M means an equivalent metal, in saso given in presensia of an auxiliary agent of reassurance and, in given saso, in the presence of a diluent, or because ( d) sulphonyl sulorides of the general formula (VI) have been reabsorbed wherein R.sup.1 and R.sup.2 have the meaning previously unsubdued, with amides of ursid (thio) sarboxylises of the general formula (VIII) Q I) H2N H. (VII where Q and R3 have the signified indisposed in the saso of the formula (I), in saso given in presensia of a aseptor of ásido and, in saso given, in presensia of a diluent, or because (e) they have been reacting sulfonylamino (thio) carbonyl somatides of the general formula (IX) wherein Q, R1 and R2 have the above-indicated meaning and Z means halogen, alkoxy, aryloxy or arylalkyloxy, with heterocyls of the general formula (V) H-R3"1 (V) in which R3-1 has the meaning previously indicated in (b), if appropriate, in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, and in a given case the compounds obtained according to processes (a), (b), (c) ), (d) and (e) are transformed into salts according to usual methods 4. Herbside agents, which are sarasterized because they have a content in at least one compound of the formula (I) or one of their salts according to claim 1. 5. Use of the compounds of general formula V (I) or their salts according to claim 1, ! 1 ^ characterized because it is the fight against the undesirable growth of plants. 6. - Procedure for lusha sontra the weeds, sarasterized because they are allowed to astuario of the general formula (I) or its salts according to claim 1, on the weeds or on its environment. 7. Process for obtaining herbeside agents, which is sarasterized because mixtures of the general formula (I) or their salts according to claim 1 are admixed with excipients and / or surfactants. 8. Sulfonamides of the general formula (II), characterized in that R1 and R2 have the meanings given in claim 1. 1. Sulfonyl isocyanate (thio) cyanates of the general formula (IV), characterized in that Q, R1 and R2 have the meanings given in claim 1. 10. Sulfonyl chlorides of the general formula (VI) characterized in that R1 and R2 have the meanings indicated in claim

1.