EP1115722A1 - SUBSTITUTED THIAZOL(IN) YLIDENEAMINO SULFONYLAMINO (THIO)CARBONYl -TRIAZOLINONES - Google Patents

Abstract

The invention relates to a novel substituted thiazol(in) ylideneamino sulfonylamino (thio)carbonyl -triazolinones of formula (I) in which Q represents oxygen or sulfur, and the radicals R?1, R2, R3, R4 and R5¿ have different meanings. The invention also relates to salts of compounds of formula (I), to methods for producing the novel compounds and to their use as herbicides.

Description

SUBSTITUTED THIAZOL (IN) YLIDENAMINO SULFONYLAMINO (THIO) CARBONYL -TRIAZOLINONE

The invention relates to new substituted thiazole (in) ylidenaminosulfonylamino- (thio) carbonyl-triazolinones, several processes for their preparation and their use as herbicides.

It is already known that certain substituted thiazole (in) ylidene aminosulfonylamino (thio) carbonyl triazolinones have herbicidal properties (cf. EP 341 489, EP 422 469, EP 425 948, EP 431 291, EP 507 171, WO 93 / 24482, WO

94/08979, WO 95/27703, WO 96/22982). However, the action of these compounds is not satisfactory in all respects.

The new substituted thiazoli (di) nyliminosulfonylamino (thio) carbonyltriazolinones of the general formula (I)

in which

Q represents oxygen or sulfur,

R represents hydrogen, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, alkenyl, alkynyl, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 represents hydrogen, cyano, halogen or an optionally substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, alkenyloxy, alkenylthio, alkenylamino, cycloalkyl, cycloalkylalkyl, cycloalkyloxy , Cycloalkylthio, cycloalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio and arylalkylamino,

R3 represents an optionally substituted radical from the series alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl and arylalkyl,

R4 represents hydrogen, cyano, halogen or optionally substituted alkyl,

R5 represents hydrogen, cyano, halogen or optionally substituted alkyl,

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

The general formula (I) represents the sum of the general by the following

Formulas (IA) and (IB) defined compounds.

(IA) (IB) Q, Rl, R ^, R3, R4 _nd R ^ have the same meaning in the general formulas (IA) and (IB) which are specified above in the definition of the compounds of general formula (I). If the compounds of the formula (IB) R ⁴ and R ^{5 are} both different from hydrogen, cis / trans isomerism can occur; the invention comprises both isomers and cis / trans mixtures with any isomer ratio.

The new compounds of general formula (I) are obtained when

(a) chlorosulfonylamino (thio) carbonyltriazolinones of the general formula (II)

in which

Q, R ^ and R ^ have the meaning given above,

with iminothiazoli (di) nen of the general formula (III)

in which

R, R ^ and R ^ have the meaning given above,

- or with acid adducts of compounds of the general formula (III) ^{^} in the presence of a diluent, - optionally in the presence of a reaction auxiliary and if appropriate

and optionally converting the compounds of the formula (I) thus obtained into salts by customary methods,

or if you

(b) triazolinones of the general formula (IV)

in which

Rl and R ^ have the meaning given above,

with chlorosulfonyl iso (thio) cyanate of the general formula (V)

Cl-SO ₂ -N = C = Q (V)

in which

Q has the meaning given above,

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

and the chlorosulfonylamino (thio) carbonyltriazolinones of the general formula (II) formed in this way in which

Q, Rlund R ^ have the meaning given above,

with iminothiazoli (di) nen of the general formula (III)

in which

R ^, R4 and R ^ have the meaning given above,

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

and optionally converting the compounds of the formula (I) thus obtained into salts by customary methods.

Further possible production methods for the compounds of the general formula (I) according to the invention are listed below, where each Q, R, R ^, R- \ R4 and R ^ have the meaning given above.

(c) reaction of triazolinone derivatives of the general formula (VI) in which

Q, Rl and R ^ have the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

with aminosulfonyliminothiazoli (di) nen of the general formula (VII)

in which

R ^, R ^ and R ^ have the meaning given above,

optionally in the presence of an acid acceptor and optionally in

Presence of a diluent,

(d) reaction of triazolinones of the general formula (IV)

in which R and R ^ have the meaning given above,

with sulfamide derivatives of the general formula (IX)

in which

Q, R ^, R ^ and R ^ have the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

optionally in the presence of an acid acceptor and optionally in the presence of a diluent.

The new compounds of the general formula (I) are notable for strong herbicidal activity.

The following also applies to the definitions in formula (I):

Q preferably represents oxygen or sulfur.

R preferably represents hydrogen, amino, Ci-C-alkylidene amino, Ci optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C 1-4 alkyl-carbonyl or Ci-C i-alkoxy-carbonyl -Cg- alkyl, for C2-Cg-alkenyl or C2-Cζ- alkynyl, optionally substituted by fluorine, chlorine and / or bromine, for Ci-Cg-alkyloxy or C2-Cö-alkenyloxy, for each optionally substituted by fluorine and / or chlorine Cj-Cg- ^" " alkylamino, di- (Cι-C4-alkyl) -amino or Cι -C4-alkanoylamino, for each optionally substituted by fluorine, chlorine, bromine and / or C1 - C4-alkyl substituted C3-C6-cycloalkyl or C3-C6-cycloalkyl-Cι -C4-alkyl, or for each optionally by fluorine, chlorine, bromine, cyano, nitro, C1 -C4-

Alkyl, trifluoromethyl, C1 -C4 alkoxy and / or -C -C4 alkoxy carbonyl substituted phenyl or phenyl-Ci -C4-alkyl.

R2 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-

Alkylthio, C1 -C4 alkylsulfinyl, -C-C ₄ -alkylsulfonyl, Cι-C4-alkyl-carbonyl, Cι-C4-alkoxycarbonyl or C -Cg-cycloalkyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by fluorine, chlorine and / or bromine

Alkenyl, alkenyloxy, alkenylthio or alkenylamino each having 2 to 6 carbon atoms in the alkenyl groups, for alkynyl having 2 to 6 carbon atoms, for cycloalkyl, cycloalkylalkyl, cyclo which are optionally substituted by fluorine, chlorine, bromine, cyano and / or C1-C4-alkyl - alkyloxy, cycloalkylthio or cycloalkylamino, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, for each optionally by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4- Alkoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino.

R ^ preferably represents optionally by cyano, carboxy, carbamoyl, fluorine,

Chlorine, C1-C4-alkoxy, -C4-alkylthio, -C4-alkylsulfinyl, C ₁ -C ₄ -alkyl-sulfonyl, Cι-C4-alkyl-carbonyl, Cι-C4-alkoxy-carbonyl, Cj-C4-alkyl- amino-carbonyl or di-Ci-C4-alkyl-amino-carbonyl substituted alkyl with

1 to 6 carbon atoms, optionally by cyano, fluorine, chlorine or C1 -C4 alkoxy substituted alkoxy having 1 to 6 carbon atoms, for each optionally substituted by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 alkoxy carbonyl, C 1 -C 4 Alkylamino-carbonyl or di-Cι-C4-alkyl-amino-carbonyl-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, C1-C4-alkyl, C1 - C4-alkyl-carbonyl, C \ -C4-alkoxy-carbonyl, C \ -C4-alkylamino-carbonyl or di-Cι-C4-alkyl-amino-carbonyl-substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, or for in each case optionally substituted by nitro, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine or by (in each case optionally substituted by fluorine and / or chlorine) C1-C4-alkyl, C1-C4- Alkoxy, C1 -C4 alkylthio, C ^ - C4 alkylsulfinyl, Ci -C4 alkylsulfonyl substituted phenyl or benzyl.

R4 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine.

R5 preferably represents hydrogen, cyano, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and or chlorine.

The invention further preferably relates to sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri (Cι- C4-alkyl) -ammonium-, tetra- (Cι-C4-alkyl) -ammonium-, tri- (C-C4-alkyl) -sulfonium-, C5- or Cg-cycloalkyl-ammonium- and di- (Cι-C2 ~ alkyl) -benzyl-ammonium salts of compounds of the formula (I) in which Q, R, R ^, R3, R _and d R5 have the meanings given above as preferred. A preferred group are the compounds of the general formula (IA) in which Q, R, RS R3, R.4 _and R ^ have the meanings given above as preferred.

Another preferred group are the compounds of the general formula (IB), in which Q, R% R ^, R3 _; R _U and R-> have the meanings given above as preferred.

Q particularly preferably represents oxygen or sulfur.

R particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, for ethenyl, propenyl, butenyl, propenyl or butynyl optionally substituted by fluorine, chlorine or bromine Methoxy, ethoxy, n- or i-propoxy or for allyloxy, for methylamino, ethylamino, n- or i-

Propylamino, dimethylamino or diethylamino, or for cyclopropyl optionally substituted by fluorine, chlorine, bromine, methyl or ethyl.

R ^ particularly preferably represents chlorine or bromine, in each case optionally by fluorine, chlorine, bromine, cyano, methoxy, ethoxy, methylthio, ethylthio,

Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, n-, i-, s- or t-Butylsulfinyl, n-, i-, s- or t-butylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each if appropriate fluorine, chlorine and / or bromine-substituted ethenyl, propenyl, butenyl, ethenyloxy, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, for propynyl, butynyl, propynyloxy, butynyloxy,

Propynylthio or butynylthio, each optionally with fluorine, chlorine, Bromine, cyano and / or methyl substituted cyclopropyl, cyclobutyl, cyclo- - - pentyl, cyclohexyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, each optionally with fluorine, chlorine, bromine Cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino.

particularly preferably represents in each case optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio,

Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl or diethylaminocamino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each methoxy, ethoxy, n- or i-propoxy optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or diethylamino carbonyl substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally with cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acety l, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or diethylamino-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclobutylmethyl, cyclobutylmethyl Cyclohexylmethyl, or for in each case optionally substituted by nitro, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, or by (in each case optionally substituted by fluorine and / or chlorine) methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted phenyl or benzyl.

R ^ particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine.

R ^ particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine.

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.

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

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

If, for example, 2-chlorosulfonylaminocarbonyl-5-ethoxy-4-methyl-2,4-dihydro-3H-1, 2,4-triazol-3-one and 3-ethoxy-3H-thiazol-2-ylidenamine are used as starting materials , the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, 4-ethyl-5-methylthio-2,4-dihydro-3H-l, 2,4-triazol-3-one and chlorosulfonyl isocyanate and then 3- (2-chloro-ethyl) -thiazolin-2-ylidenamine are used as Starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the chlorosulfonylamino (thio) carbonyltriazolinones to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In formula (II), Q, R and ^~ R2 preferably or in particular have those meanings that already above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for Q, Rl and R ^.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. WO 94/08979, WO 95/27703).

Formula (III) provides a general definition of the iminothiazoles (di) ne to be used as starting materials in processes (a) and (b) according to the invention; the compounds of the formula (III) can also be referred to as thiazole (in) ylidenamines. In the formula (III), R ^, R4 and R ^ 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) according to the invention preferably or as particularly preferred for R ^, R4 and R. ^ were specified.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. WO 93/00336 / EP 592676).

The triazolinones to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I) are represented by the formula

(IV) generally defined. In the formula (IV), R and R ^ preferably or in particular have those meanings which have been given above or in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R * and R ^.

The starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf. EP 283 876, EP 294666, EP 301 946, EP 298 371, EP 341 489, EP 399 294, EP 398 096, EP 422 469, EP 425 948, EP 431 291, EP 477 646). Processes (a) and (b) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out using diluents. Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane,

Heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and

ethyl ester, nitriles such as e.g. Acetonitrile and propionitrile, amides such as e.g. Dimethylformamide, dimethylacetamide and N-methylpyrrolidone as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric acid triamide.

Acid acceptors which can be used in processes (a) and (b) according to the invention are all acid binders which can customarily be used for such reactions. Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g. Calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium tert-butoxide, and also basic nitrogen compounds such as trimethylamine, triethylamine,

Tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethylaniline, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl -, 2,6-Dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, l, 5-diazabicyclo [4,3,0] -non-5-ene (DBN) , 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] -octane

(DABCO).

The reaction temperatures can be varied within a substantial range in processes (a) and (b) according to the invention. In general, temperatures between -20 ° C and + 80 ° C, preferably at temperatures between 0 ° C and + 50 ° C Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.

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

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

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,

Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus,

Apera, Aegilops, Phalaris.

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

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

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop- plants, on ornamental and sports turf and pastures and for selective weed control in annual crops. The. Compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when applied to above-ground parts of plants; some of them are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.

To a certain extent, the compounds of the formula (I) according to the invention also show fungicidal activity, for example against Oomycetes and against Fusarium.

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

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters. Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar

Solvents such as dimethylformamide and dimethyl sulfoxide, and water. As. solid carriers are possible: for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are possible as solid carriers for granules : eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl) Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidaz, Chloronben, Chloramben, Chloramben, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), methyloransulamam, Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefüron, dimepiperate, dimethachlor, dimethamet ryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid-Fenoxapanid, Fenoxap Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtetamone - Flu- methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (- isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic,

Imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, ioxynil, iso- propalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metobromuron, metobromuron, metobromuron Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orben-carb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquathamine, Paraquathamine Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyim, Pyribenzoxarbfen, Pyribenzoxarbfen

Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, Terbuthylazine, ter- Butryn, Thiafluamide, thiazopyr, thidiazimin, thifensulfuron thenylchlor (- methyl), uron thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, Triben- ( -methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

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

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing. The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

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

Preparation Examples:

example 1

(Method (b))

A solution of 1.7 g (10 mmol) of 3- (3-fluoropropyl) -3H-thiazol-2-ylidenamine and 1.2 g (12 mmol) of triethylamine in 5 ml of methylene chloride is at room temperature (approx. 20 ° C) with stirring to a mixture of 1.5 g (10 mmol) of 5-ethoxy-4-methyl

2,4-dihydro-3H-l, 2,4-triazol-3-one, 1.5 g (10 mmol) of chlorosulfonyl isocyanate and 50 ml of methylene chloride added dropwise. The reaction mixture is stirred for about 30 minutes at room temperature, then washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with isopropanol and the crystalline product is isolated by suction.

2.2 g (54% of theory) of 2 - [(3-fluoropropyl) -3H-thiazol-2-ylideneaminosulfonylaminocarbonyl] -5-ethoxy-4-methyl-2,4-dihydro-3H- 1, 2,4-triazol-3-one with a melting point of 178 ° C.

Analogous to production example 1 and in accordance with the general description of the production processes according to the invention, for example, those in FIG Compounds of the formula (I) - or of the formulas (IA) and (IB) - listed in Table 1 below.

(IA) (IB)

Table 1: Examples of the compounds of the formula (I) - of the formulas (IA) and (IB)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

annotation

The (greatly reduced) radical R ¹ in Example 139 has the following meaning:

Examples of use:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, the compounds according to Preparation Examples 1, 29, 30, 33, 51, 56, 124, 125, 130 and 131, for example, show very strong activity against weeds, in some cases with good tolerance to crop plants, such as, for example, maize and sugar beets. Table A: Pre emergence test / greenhouse

Active ingredient according to Auf and- Mais Zucker- Echino- Setaria Ama- Matri- Vero-

Production example no. quantity (g ai./ha) beets chloa ranthus caria nica

(124) 125 90 95 70 100 95

Table A (continued):

Active ingredient according to preparation example no. Effort- Digi- Echino- Ama- Cheno-Matri- Vero amount (g ai./ha) taria chloa ranthus podium caria nica

(29) 125 95 100 100 95 100

(30) 125 90 95 100 100 100 100

Table A (continued):

Active ingredient according to preparation example no. Effort- Digi- Echino- Ama- Cheno-Matri- Vero amount (g ai./ha) taria chloa ranthus podium caria nica

(33) 125 80 100 100 100 95

Table A (continued):

Active ingredient according to expenditureEchino- Setaria Ama- Matri- Vero-

Production example no. quantity (g ai./ha) chloa ranthus caria nica

(1) 60 100 100 100 100 100

Table A (continued):

Active ingredient according to expenditureEchino-Ama- Cheno-Matri-Vero Production example no. quantity (g ai./ha) chloa ranthus podium caria nica

(125) 125 90 70 95 100 100

Table A (continued):

Active ingredient according to expenditure Echino Ama- Cheno Matri Vero

Production example no. quantity (g ai./ha) chloa ranthus podium caria nica

(130) 125 100 100 100 100 100

(131) 125 80 100 95 100 95

Table A (continued):

Active ingredient according to expenditureSetaria Ama-Cheno-Matri-Vero Production example no. quantity (g ai./ha) ranthus podium caria nica

(56) 250 100 100 100 100 100

Table A (continued):

Active ingredient according to effort- Ama- Cheno-Matri-Vero Production example no. quantity (g ai./ha) ranthus podium caria nica

(51) 125 100 95 100 100

Example B

Post emergence test

Solvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 1, 2, 9, 33, 34, 41, 48, 49, 55, 125, 130 and 131 show very strong activity against

Weeds. Table B: Post emergence test / greenhouse

Active ingredient according to effort- Setaria Abu- Ama- Cheno- Sola- StelManufacturing example no. quantity (g ai./ha) tilon ranthus podium num laria

(2) 60 90 90 90 95 90

Table B (continued):

Active ingredient according to effort- Setaria Abu- Ama- Cheno- Sola- StelManufacturing example no. quantity (g ai./ha) tilon ranthus podium num laria

(33) 125 80 100 100 100 95 95

(34) 125 70 95 100 100 100 100

Table B (continued):

Active ingredient according to expenditureSetaria Abu- Ama- Cheno- Sola- Stel- Manufacturing sample no. quantity (g ai./ha) tilon ranthus podium nu laria

(41) 125 70 90 90 90 95

Table B (continued):

Active ingredient according to expenditureSetaria Abu- Ama- Cheno- Sola- Stel- Manufacturing sample no. quantity (g ai./ha) tilon ranthus podium num laria

(49) 125 70 100 100 95 95

(55) 125 95 100 100 90 100

Table B (continued):

Active ingredient according to expenditure Echino-Sor-Ama- Poly-Vero Production example no. amount (g ai./ha) chloa ghum ranthus gonum nica

(1) 60 95 95 95 90 90

Table B (continued):

Active ingredient according to effortAbu- Poly-Sola- Stel- Manufacturing sample no. quantity (g ai./ha) tilon gonum num laria

(125) 60 90 90 90 90

Table B (continued):

Active ingredient according to expenditureAbu- Ama- Cheno-Matri- Stel- Vero - Production example no. quantity (g ai./ha) tilon ranthus podium caria laria nica

(130) 60 95 100 100 100 95 100

(131) 60 90 100 95 95 95 90

Claims

claims

1. Substituted thiazole (in) ylidenamino sulfonylamino (thio) carbonyl-triazolinone ones of the general formula (I),

in which

represents oxygen or sulfur,

R1 represents hydrogen, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, alkenyl, alkynyl, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl,

R2 represents hydrogen, cyano, halogen or an optionally substituted radical from the series alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, alkenyloxy, alkenylthio, alkenylamino, cycloalkyl, cycloalkylalkyl,

Cycloalkyloxy, cycloalkylthio, cycloalkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio and arylalkylamino, R3 represents an optionally substituted radical from the series alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl and arylalkyl,

R4 represents hydrogen, cyano, halogen or optionally substituted alkyl,

R5 represents hydrogen, cyano, halogen or optionally substituted alkyl,

and salts of compounds of formula (I).

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

Q represents oxygen or sulfur,

Rl for hydrogen, amino, C ^ -Cg-alkylideneamino, for C ^ optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, Ci-Ci-alkylcarbonyl or Cι-C-ι-alkoxy-carbonyl -Cg- alkyl, for each optionally substituted by fluorine, chlorine and / or bromine C ₂ -Cö-alkenyl or C ₂ -Cg-alkynyl, for Ci -Cg-alkyloxy or C ₂ -Cg-alkenyloxy, each optionally substituted by fluorine and / or chlorine-substituted Cj-Cg-alkylamino, di- (-C-C-ι-alkyl) -amino or Cι-C4-alkanoylamino, each optionally with fluorine, chlorine,

Bromine and / or C1-C4.-A.kyl substituted C -C6 cycloalkyl or C ₃ -C (5-cycloalkyl-Cι-C4-alkyl, or for each optionally by fluorine, chlorine, bromine, cyano, nitro, C1 -C4- alkyl, trifluoromethyl, Cj- C4- alkoxy and / or Cι-C4-alkoxy-carbonyl-substituted phenyl or phenyl-C 1 -C4-alkyl, R2 for hydrogen, cyano, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, bromine, cyano, -C-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, Ci-C ^ alkylsulfonyl, C ^ -alkyl carbonyl, -C-C4-alkoxy-carbonyl or C ₃ -Cg-cycloalkyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl,

Alkylamino or dialkylamino, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylthio or alkenylamino, each optionally substituted by fluorine, chlorine and / or bromine, each having 2 to 6 carbon atoms in the alkenyl groups, for alkynyl having 2 to 6 Carbon atoms for cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino, each optionally substituted by fluorine, chlorine, bromine, cyano and / or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, for each optionally by fluorine, chlorine,

Bromine, cyano, nitro, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino,

R3 for optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4- alkylsulfinyl, C1-C4- alkylsulfonyl, Cι-C4-alkylcarbonyl, Cι-C4- Alkoxy-carbonyl, C1-C4-alkylamino-carbonyl or Di-Cι-C4-alkyl-amino-carbonyl-substituted alkyl having 1 to 6 carbon atoms, for alkoxy optionally substituted by cyano, fluorine, chlorine or C1-C4-alkoxy 1 to 6 carbon atoms, each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 alkoxy carbonyl, C 1 -C 4 alkylamino carbonyl or di-C 1 -C 4 -alkyl-amino-carbonyl-substituted alkenyl or alkynyl

- With 2 to 6 carbon atoms each, each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, C1-C4-alkyl, -C-C4-alkyl-carbonyl, Cι-C4-alkoxy-carbonyl, C _j -C4-alkylamino-carbonyl or di-Cι-C4- alkyl-amino-carbonyl-substituted cycloalkyl or cycloalkylalkyl, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, or by (in each case substituted by fluorine and / or chlorine substituted) C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, Cj-C4-alkylsulfonyl-substituted phenyl or benzyl,

R4 represents hydrogen, cyano, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine, and

R5 represents hydrogen, cyano, fluorine, chlorine, bromine or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine,

as well as the sodium, potassium, magnesium, calcium, ammonium, C1-C4

Alkyl ammonium, di (C 4 -C 4 alkyl) ammonium, tri (C 4 -C 4 alkyl) ammonium, tetra (C 1 -C 4 alkyl) ammonium, tri (-C-C4-alkyl) sulfonium, C5 or Cg-cycloalkyl-ammonium and di- (-C ^ C -alkyl) -benzyl-ammonium salts of compounds of formula (I).

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

Q represents oxygen or sulfur, Rl for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, for ethenyl, propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy , n- or i-propoxy or for allyloxy, for methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for cyclopropyl optionally substituted by fluorine, chlorine, bromine, methyl or ethyl,

R represents chlorine or bromine, each optionally by fluorine, chlorine,

Bromine, cyano, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, n-, i-, s- or t-butylsulfinyl, n-, i-, s- or t-butylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, ethenyloxy which are each optionally substituted by fluorine, chlorine and / or bromine,

Propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, for propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyl, optionally substituted in each case by fluorine, chlorine, bromine, cyano and / or , Cyclopropyloxy,

Cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, for each phenyl, phenoxy, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio, phenylthio

- Benzylthio or Benzylamino stands, R3 for each optionally by cyano, carboxy, carbamoyl, fluorine,

Chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,

5 ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or diethylamino-carbonyl substituted methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, for each optionally by cyano,

10 fluorine, chlorine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl , Methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino

15 carbonyl or diethylamino carbonyl substituted ethenyl,

Propenyl, butenyl, ethynyl, propynyl or butynyl, each in each case optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-

20 carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-

Propylaminocarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro,

25 cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, or by (in each case optionally substituted by fluorine and or chlorine substituted) methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl sub-

30 substituted phenyl or benzyl, R represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine, and

R5 for hydrogen, cyano, fluorine, chlorine, bromine or optionally through

Fluorine and / or chlorine substituted methyl, ethyl, n- or i-propyl.

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

(a) chlorosulfonylamino (thio) carbonyltriazolinones of the general formula (II)

in which

Q, Rl and R2 have the meaning given in claim 1,

with iminothiazoli (di) nen of the general formula (III)

in which

R3, R4 and R ^ have the meaning given in claim 1, - or with acid adducts of compounds of the general formula (III) -

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

and optionally converting the compounds of the formula (I) thus obtained into salts by customary methods,

or that one

(b) triazolinones of the general formula (IV)

in which

Rl and R have the meaning given above,

with chlorosulfonyl iso (thio) cyanate of the general formula (V)

Cl-SO ₂ -N = C = Q (V)

in which

Q has the meaning given above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and the chlorosulfonylamino (thio) carbonyltriazolinones of the general formula (II) formed in this way

in which

Q, Rlund R2 have the meaning given above,

with iminothiazoli (di) nen of the general formula (III)

in which

R3, R4 and R5 have the meaning given above,

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

and optionally converting the compounds of the formula (I) thus obtained into salts by customary methods.

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

6. Use of compounds of formula (I) according to claim 1 for combating undesirable plant growth.

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

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