DE19525974A1 - Substituted arylsulfonylamino (thio) carbonyltriazolin (thi) one - Google Patents

Abstract

The invention relates to novel substituted aryl sulphonyl amino (thio) carbonyl triazolin(thi)ones of formula (I) in which Ar is possibly substituted arylene or heteroarylene; Q<1> is oxygen or sulphur; Q<2> is oxygen or sulphur; R<1> is hydrogen, hydroxy, amino, alkylidene amino or a possibly substitued radical from the series alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkyl alkyl, aryl, arylalkyl; R<2> is hydrogen, hydroxy, mercapto, amino, halogen or a possibly substituted radical from the series alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, alkenylamino, alkinylamino, dialkylamino, alkanoylamino, aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl alkyl, cycloalkyl alkoxy, cycloalkyl alkylthio, cycloalkyl alkylamino, aryl, aryloxy, arylthio, arylamino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyloxy, heterocyclylthio; or R<1> and R<2> together are possibly branched alkandiyl; and R<3> is possibly substituted heterocyclyl; and salts of the compounds of formula (I), process for producing the novel compounds and their use as herbicides.

Description

The invention relates to new substituted arylsulfonylamino (thio) carbonyltriazoline (thi) one, several processes for their production and their use as Herbicides.

It is already known that certain sulfonylaminocarbonyltriazolinones are herbicidal Have properties (cf. EP-A 341489, EP-A 422469, EP-A 425948, EP-A 431291, EP-A 507171). The effect of these compounds, however, is not in all Satisfactory.

The new substituted arylsulfonylamino (thio) carbonyltriazoline (thi) one of the general formula (I),

in which
Ar represents optionally substituted arylene or heteroarylene,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ represents hydrogen, hydroxy, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,
R² is hydrogen, hydroxyl, mercapto, amino, halogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenyiamino, alkynylamino, dialkylamino, alkanoyl amino , Aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cyclo alkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, aryl oxy, arylthio, arylamino, arylloxy, arylyloxy, arylyloxy, arylyloxy, arylyloxy, arylalkyl, arylalkyl, arylyloxy , or
R¹ and R² together represent optionally branched alkanediyl, and
R³ represents optionally substituted heterocyclyl,
as well as salts of the compounds of formula (I).

The new substituted arylsulfonylamino (thio) carbonyl-triazoline (thi) one of the general formula (I), if one

• (a) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given above, with substituted arylsulfonyliso (thio) cyanates of the general formula (III) R³-O-CO-Ar-SO₂-N = C = Q² (III) in which
  Ar, Q² and R³ have the meanings given above,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  or if you
• (b) triazolin (thi) on derivatives of the general formula (IV) in which
  Q¹, Q², R¹ and R² have the meanings given above and
  Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  with sulfonic acid amides of the general formula (V) R³-O-CO-Ar-SO₂-NH₂ (V) in which
  Ar and R³ have the meanings given above,
  if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
  or if you
• (c) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given above,
  with substituted arylsulfonic acid amide derivatives of the general formula (VI) R³-O-CO-Ar-SO₂-NH-CQ²-Z (VI) in which
  Ar, Q² and R³ have the meanings given above and
  Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
  or if you
• (d) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given above,
  with substituted arylsulfonic acid halides of the general formula (VII) R³-O-CO-Ar-SO₂-X (VII) in which
  Ar and R³ have the meanings given above and
  X represents halogen,
  and metal (thio) cyanates of the general formula (VIII) MQ²CN (VIII) in which
  Q² has the meaning given above and
  M represents an alkali metal or an alkaline earth metal equivalent,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  and optionally the compounds of the formula (1) obtained by processes (a), (b), (c) or (d) are converted into salts by customary methods.

The new sulfonylamino (thio) carbonyl-triazolin (thi) one of the general formula (I) are characterized by a strong herbicidal activity.

The invention preferably relates to compounds of the formula (I) in which
Ar for each optionally by halogen, cyano, nitro, by C₁-C₄-alkyl, C₁-C₄-alkoxy, C £ -C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkyl sulfonyl, di- (C₁-C₄ -alkyl) -amino-sulfonyl or N-C₁-C₄-alkoxy-N-C₁-C₄-alkyl-amino-sulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted phenylene or naphthylene, or for optionally by halogen , Cyano, Nitro, by C₁-C₄-alkyl or C₁-C₄-alkoxy (which are each optionally substituted by fluorine and / or chlorine) substituted heteroarylene having 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two other nitrogen,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for hydrogen, hydroxy, amino, for C₂-C₁₀-alkylideneamino, for optionally C₁- substituted by fluorine, chlorine, bromine, cyano, C₁-C₄-alkoxy, C₁-C₄-alkyl carbonyl or C₁-C₄-alkoxy-carbonyl C₆-alkyl, for each optionally substituted by fluorine, chlorine and / or bromine, C₂- C₆-alkenyl or C₂-C₆-alkynyl, for each optionally by fluorine, chlorine, cyano, C₁-C₄-alkoxy or C₁-C₄-alkoxy- carbonyl substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino or C₁-C₆-alkanoylamino, for C₃-C₆-alkenyloxy, for di- (C₁-C₄-alkyl) -amino, each optionally with fluorine, chlorine, bromine, Cyano and / or C₁-C₄-alkyl substituted C₃-C₆-cycloalkyl or C₃-C₆-cydoalkyl-C₁-C₄-alkyl, or for any given case by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, Trifluoromethyl and / or C₁-C₄-alkoxy substituted phenyl or phenyl-C₁-C₄-alkyl,
R² for hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, iodine, for optionally by fluorine, chlorine, bromine, cyano, C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxy-carbonyl substituted C₁-C₆-alkyl, for each optionally substituted by fluorine, chlorine and / or bromine substituted C₂-C₆-alkenyl or C₂-C₆-alkynyl, each optionally substituted by fluorine, chlorine, cyano, C₁-C₄-alkoxy or C₁-C₄ -Alkoxy-carbonyl substituted C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or C₁-C₆-alkanoyl amino, for C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-alkenylthio, C₂ - C₆-Alkynylthio, C₂-C₆-alkenylamino or C₂-C₆-alkynylamino, for di- (C₁-C₄-alkyl) -amino, for aziridino, pyrrolidino, piperidino or morpholino, each optionally substituted by methyl and / or ethyl C₃-C₆-cycloalkyl, C₅-C₆- optionally substituted by fluorine, chlorine, bromine, cyano and / or C₁-C₄- alkyl Cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl -C₁-C₄ alkylthio or C₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or for each where appropriate by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, trifluoromethyl and / or C₁-C₄-alkoxy substituted substituted phenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio, phenyl-C₁-C₄ alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or for each optionally by fluorine, chlorine , Bromine, cyano, nitro, C₁-C₄ alkyl, trifluoromethyl and / or C₁-C₄ alkoxy substituted heterocyclyl oxy or heterocyclylthio, where in each case the heterocyclyl component from the series oxiranyl, oxetanyl, furyl, tetrahydrofuryl, thietanyl, thienyl Tetrahydrothienyl is selected, or
R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and
R³ represents oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetrahydrothienyl optionally substituted by halogen or C₁-C₄-alkyl.

The invention further preferably relates to sodium, potassium, Magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di- (C₁-C₄-alkyl) ammonium-, tri- (C₁-C alkyl-alkyl) -ammonium-, tetra- (C₁-C₄-alkyl) -ammonium-, tri- (C₁-C₄ alkyl) sulfonium, C₅ or C₆ cycloalkyl ammonium and di (C₁-C₂ alkyl) benzyl ammonium salts of compounds of the formula (1) in which Ar, Q¹, Q², R¹, R² and R³ have the meanings preferably given above.

The invention relates in particular to compounds of the formula (1) in which
Ar for 1,2-phenylene (ortho-phenylene) which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio or ethylthio , Pyridine-2,3-diyl, thiophene-2,3-diyl or pyrazole-4,5-diyl,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for hydrogen, hydroxy, amino, for C₃-C₈-alkylideneamino, for each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for prenpenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyloxy or butenyl oxy, for dimethylamino or diethylamino, each optionally with fluorine , Chlorine, methyl and / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl methyl, cyclopentylmethyl or cyclohexylmethyl, or for phenyl or benzyl which is optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy
R² for hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or substituted by fluorine, chlorine, cyano, methoxy or ethoxy t-butyl, for propenyl, butenyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, i-, 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, for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, for dimethylamino, diethylamino or dipropylamino, for each, if appropriate, by fluorine Methyl and / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyc lopentenyl, cyclohexenyl, cyclo propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyl thio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, Cyclobutylmethylthio , Cyciopentylmethylthio, Cyclohexylmethylthio, Cyclopropylmethylamino, Cyclobutylmethylamino, Cyclopentylmethylamino or Cyclohexylmethylamino, or for each optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy represents phenyl, benzyl, phenoxy, benzylamino or phenylamino, phenylamino, phenylthioamino, phenylthioamino, phenylthioamino each optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy oxetanyloxy, furyloxy, tetrahydrofuryloxy, thienyloxy or tetrahydro thienyloxy, or
R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and
R³ represents in each case optionally substituted by fluorine, chlorine, methyl or ethyl oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetra hydrothienyl.

A very particularly preferred group of compounds of formula (I) are Compounds of formula (Ia)

in which
Q¹, Q², R¹, R² and R³ have the meanings given above as being particularly preferred.

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

For example, 2- (oxetan-3-yl-oxy-carbonyl) -phenylsulfonyliso is used cyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting substances, the course of the reaction in process (a) according to the invention can be carried out the following formula scheme are outlined:

For example, 2- (thietan-3-yl-oxy-carbonyl) -benzenesulfonamide is used and 2-chlorocarbonyl-4-dimethylamino-5-methyl-2,4-dihydro-3H-1,2,4-triazo-l-3- thione as starting materials, the course of the reaction in the invention Process (b) are outlined by the following formula scheme:

For example, one uses N-methoxycarbonyl-2- (2-tetrahydrofuryl-methoxy carbonyl) benzenesulfonamide and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazole 3-one as starting materials, so the course of the reaction in the invention Process (c) can be outlined by the following formula scheme:

For example, if 4-ethyl-5-ethylthio-2,4-dihydro-3H-1,2,4-triazole-3- is used on and 2- (3-thietanyl-oxy-carbonyl) -benzenesulfochloride and potassium cyanate as Starting materials, so the course of the reaction in the process according to the invention (d) are sketched by the following formula scheme:

The processes (a), (c) and (d) for the preparation of Compounds of the formula (I) triazoline (thi) to be used as starting materials one are generally defined by formula (II). In formula (II), Q¹, R¹ have and R² preferably or in particular those meanings which have already been given above in connection with the description of the compounds according to the invention of formula (I) preferably or as particularly preferred for Q¹, R¹ and R² were specified.

The triazolin (thi) one of the general formula (II) are known and / or can can be produced by processes known per se (cf. Arch. Pharm. 301 (1968), 827; loc. cit. 1974, 307: 889; Bull. Soc. Chim. France 1962, 1365; loc. cit. 1975, 1191; Chem. Ber. 90 (1957) 909-921; loc. cit. 98 (1965), 3025-3099; loc. cit. 102: 755; 1969; J. Heterocycl. Chem. 15: 237-240 (1978); J. Indian Chem. Soc. 6 (1929), 565; Liebigs Ann. Chem. 637 (1960), 135; Monthly magazines  Chemie 123 (1992), 257; Tetrahedron 32 (1976) 2347-2352; Helv. Chim. Acta 63 (1980), 841-859; J. Chem. Soc. C 1967, 746-751; loc. cit. 1970, 26-34; J. Chem. Soc. Perkin 11973, 2644; Fen Fak. Derg., Seri A (Ege Univ.) 7 (1984), 1-6 cited in Chem. Abstracts 101: 90846m; EP-A 283876; EP-A 294666; EP-A 298371; EP-A 301946; EP-A 305844; EP-A 341489; EP-A 362633; EP-A 370293; EP-A 391187; EP-A 398096; EP-A 398097; EP-A 399294; EP-A 415196; EP-A 422469; EP-A 425948; EP-A 431291; EP-A 477646; EP-A 502307; EP-A 503437; EP-A 505819; EP-A 511569; EP-A 513621; DE-A 23 36 827; DE-A 38 39 206; DE- A 39 16 208; DE-A 39 16 930; DD-P 64970; WO-A 93/04050; Manufacturing case games).

The process (a) according to the invention for the preparation of compounds of Formula (I) further substituted arylsulfonyl to be used as starting materials Formula (III) generally defines iso (thio) cyanates. In the formula (III) Ar, Q² and R³ preferably or in particular have the meaning which already above in connection with the description of the Ver bonds of the formula (I) preferably or as particularly preferred for Ar, Q² and R³ was specified.

The starting materials of the formula (III) are known and / or per se known methods can be produced (cf. EP-A 496701, EP-A 558445).

The process (b) according to the invention for the preparation of the compounds of general formula (I) to be used as starting materials triazolin (thi) on Derivatives are generally defined by the formula (IV). Have in formula (IV) Q¹, Q², R¹ and R² preferably or in particular those meanings which already above in connection with the description of the connections of the Formula (I) as preferred or as particularly preferred for Q¹, Q², R¹ and R² were specified; Z preferably represents fluorine, chlorine, bromine, methoxy, Ethoxy, benzyloxy, phenoxy, halogen or nitro-phenoxy, especially for Methoxy, phenoxy or 4-nitro-phenoxy.

Some of the starting materials of the formula (IV) are not yet from the literature known and the subject of its own earlier patent applications.

The compounds of general formula (IV) are obtained when Triazolin (thi) one of the general formula (II)

in which
Q¹, R¹ and R² have the meanings given above,
with carbonic acid derivatives of the general formula (IX)

Z-CO-Z¹ (IX)

in which
Z has the meaning given above and
Z 1 represents halogen, alkoxy, aralkoxy or aryloxy (and has the same preferred meanings as Z),
optionally in the presence of an acid acceptor, such as. As sodium or potassium hydroxide, sodium or potassium t-butoxide, and optionally in the presence of a diluent, such as. As methylene chloride, tetrahydrofuran or dimethoxyethane and / or water, at temperatures between 0 ° C and 100 ° C to.

The process (b) according to the invention for the preparation of the compounds of general formula (I) sulfonic acid to be used as starting materials Amides are generally defined by the formula (V). In formula (V), Ar and R³ preferably or in particular the meaning already mentioned above in Connection with the description of the compounds of formula (I) as before added or was specified as particularly preferred for Ar and R³.

The starting materials of the formula (V) are known and / or per se known methods can be produced (cf. EP-A 496701, EP-A 558445).  

The process (c) according to the invention for the preparation of the compounds of Formula (I) substituted arylsulfonic acid to be used as starting materials Formula (VI) provides a general definition of amide derivatives. In the formula (VI) Ar, Q² and R³ preferably or in particular have the meaning which already above in connection with the description of the connections of the Formula (I) as preferred or as particularly preferred for Ar, Q² and R³ would give; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, Benzyloxy, phenoxy, halogen or nitro-phenoxy, especially for methoxy, Phenoxy or 4-nitro-phenoxy.

The starting materials of the formula (VI) are known and / or per se known methods can be produced.

The process (d) according to the invention for the preparation of the compounds of Formula (I) substituted arylsulfonic acid to be used as starting materials Halides are generally defined by the formula (VII). In formula (VII) Ar and R³ preferably or in particular have the meaning which already above in connection with the description of the compounds of the formula (I) was specified as preferred or as particularly preferred for Ar and R³; X preferably represents fluorine, chlorine or bromine, in particular chlorine.

The starting materials of formula (VII) are known and / or per se known methods can be produced (cf. EP-A 496701, EP-A 558445).

The processes (a), (b), (c) and (d) according to the invention for the preparation of the new Compounds of formula (I) are preferably made using Ver carried out fertilizers. These come in handy as diluents all inert organic solvents in question. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as Pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, ligroin, benzene, toluene, Xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorine benzene and o-dichlorobenzene; Ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; Ketones like Acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone; Esters like Methyl acetate and ethyl acetate; Nitriles such as B. acetonitrile and propio nitrile; Amides such as B. dimethylformamide, dimethylacetamide and N-methyl  pyrrolidone, as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethylphos phosphoric tri amide.

As reaction auxiliaries or as acid acceptors in the Invention Processes (a), (b), (c) and (d) all usually for such reactions usable acid binders can be used. Preferably in question come alkali metal hydroxides such. B. sodium and potassium hydroxide, alkaline earth hydroxides such as As calcium hydroxide, alkali carbonates and alcoholates such as Sodium and potassium carbonate, sodium and potassium tert-butoxide, also basic Nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributyl amine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclo hexylamine, 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 processes (a), (b), (c) and (d) can be varied over a wide range. Generally works one at temperatures between -20 ° C and + 150 ° C, preferably at Temperatures between 0 ° C and + 100 ° C.

The processes (a), (b), (c) and (d) according to the invention are in general carried out under normal pressure. However, it is also possible to increase or to work under reduced pressure.

To carry out processes (a), (b), (c) and (d) according to the invention the starting materials required in each case generally in approximately equimolar Amounts used. However, it is also possible to use one of the respectively used To use components in a larger excess. The reactions are generally in a suitable diluent in the presence an acid acceptor, and the reaction mixture becomes several Stirred for hours at the required temperature. The workup takes place in processes (a), (b), (c) and (d) in each case according to the invention usual methods (see the manufacturing examples).

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

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers, and especially as weed killers. Weeds in the broadest sense are understood to mean all plants that are in places grow up where they are undesirable. Whether the substances according to the invention as total or selective herbicides act essentially depends on the applied Amount off.

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

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, apera.

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

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

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

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocot and dicot weeds in mono cotyledonous and dicotyledon cultures both in the pre- and post-emergence Method.

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

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

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic carbons Hydrogen, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclo  hexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispergents are: B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 weight percent active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their Formulations also in a mixture with known herbicides for weeds Combat use, where ready formulations or tank mixtures are possible.  

Known herbicides are suitable for the mixtures, for example anilides, such as B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichlor picolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy alkanoic acid esters, such as. B. diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, Haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as e.g. B. Alachlor, Acetochlor, Butachlor, Metaza chlorine, metolachlor, pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, Fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, like e.g. B. chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenz thiazuron; Hydroxylamines, such as. B. alloxydim, clethodim, cycloxydim, Sethoxydim and tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, imazapyr and imazaquin; Nitriles such as B. bromoxynil, Dichlobenil and ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as B. amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, such as B. butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, Thiobencarb and triallates; Triazines, e.g. B. atrazine, cyanazine, simazine, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, Metamitron and metribuzin; Others, such as B. aminotriazole, benfuresate, Bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, Ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used will. The application is done in the usual way, e.g. B. by pouring, spraying, Spraying, spreading.  

The active compounds according to the invention can be used both before and after run of the plants can be applied. You can also sow in the soil before sowing be incorporated.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 10 g and 10 kg of active ingredient per hectare of soil area, preferably between 50 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1 (Method (d))

A mixture of 2.3 g (8 mmol) of 2-chlorosulfonyl-benzoic acid (tetrahydrofur-3- yl) ester, 1.2 g (8 mmol) of 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3 -one, 1.0 g (8 mmol) of sodium cyanate and 100 ml of acetonitrile is added for about 15 hours Stir heated to reflux. The mixture is then concentrated in a water jet vacuum Shaken residue with methylene chloride and hydrochloric acid water (pH 1), the separated organic phase, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product isolated by suction.

0.7 g (20% of theory) of 4-methyl-5-methylthio-2- [2- (tetrahydro-fur-3- yl-oxycarbonyl) -phenylsulfonyl-aminocarbonyl] -2,4-dihydro-3H-1,2,4-triazol-3 -one melting point 160 ° C.  

Example 2

(Method (d))

A mixture of 2.8 g (10 mmol) of 2-chlorosulfonyl-benzoic acid (oxetan-3-yl) ester, 1.3 g (10 mmol) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 1.3 g (20 mmol) sodium cyanate and 50 ml acetonitrile is refluxed for 90 minutes heated. It is then concentrated in a water jet vacuum and the residue stirred with methylene chloride and 1N hydrochloric acid. The organic phase then dried with sodium sulfate and filtered. The filtrate is concentrated, the back was digested with isopropanol and the resulting product crystallized Suction isolated.

1.7 g (41% of theory) of 5-ethyl-4-methyl-2- [2- (oxetan-3-yl-oxy) are obtained carbonyl) phenylsulfonylaminocarbonyl] -2,4-dihydro-3H-1,2,4-triazol - 3-one from Melting point 137 ° C.

Analogously to Examples 1 and 2 and in accordance with the general description of Manufacturing methods according to the invention can, for example, also in the Compounds of formula (I) listed below in Table 1 - or Formula (Ia) - are produced.

Table 1

Examples of the compounds of the formula (Ia)

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

A solution of 3.4 g of pyridine in 20 ml of methylene chloride is at -10 ° C. Stirring to a mixture of 9.46 g (39 mmol) of 2-chlorosulfonyl-benzoyl chloride, 3.5 g (39 mmol) 3-hydroxymethyl-tetrahydrofuran and 100 ml methylene chloride added dropwise and the reaction mixture is then at about 6 hours Stirred at 20 ° C. The mixture is then concentrated in a water jet vacuum, the back stood shaken with methylene chloride and hydrochloric acid water (pH 1), the separated organic phase, dried with sodium sulfate and filtered. From Filtrate, the solvent is carefully distilled off in a water jet vacuum.

8.2 g (72.5% of theory) of 2-chlorosulfonylbenzoic acid (tetrahydrofuran) are obtained. 3-yl) ester as an oily residue, which as such is used directly for further reactions can be used.

Example VII-2 step 1

A mixture of 68.3 g (0.20 mol) of bis (2-chlorocarbonylphenyl) disulfide, 29.6 g (0.40 mol) 3-hydroxy-oxetane, 42.5 g (0.42 mol) triethylamine and 500 ml Methylene chloride is stirred at 20 ° C for 15 hours. Then 200 ml of 1N salt acid added, the organic phase separated, washed with water, with Dried sodium sulfate and filtered. The filtrate is in a water jet vacuum concentrated, the residue digested with diethyl ether and this crystallized falling product isolated by suction.

48.6 g (58% of theory) of bis- [2- (oxetan-3-yl-oxycarbonyl) phenyl] are obtained. disulfide with a melting point of 143 ° C.

Level 2

In a mixture of 10.5 g (25 mmol) of bis- [2- (oxetan-3-yl-oxycarbonyl) phenyl] disulfide, 12.9 g sodium acetate and 100 ml 50% aqueous acetic acid at -5 ° C to 0 ° C 11.2 g of chlorine introduced within about 15 minutes. The Re Action mixture is stirred for 15 minutes at 0 ° C and with 150 ml of methylene chloride added. Then the methylene chloride phase is separated off with ice water washed, dried with sodium sulfate and filtered. The filtrate is in the water jet vacuum concentrated and the residue by two column chromatography graph on silica gel (first run with methylene chloride, second run with vinegar acid ethyl ester) cleaned.

10.4 g (75% of theory) of 2-chlorosulfonylbenzoic acid (oxetan-3-yl) are obtained. ester as a yellowish oil.

1 H-NMR (CDCl₃, TMS, δ): 4.9 (m, 2H), 5.0 (m, 2H), 5.8 (m, 1H), 7.8 (m, 3H), 8.2 (m, 1H) ppm.  

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 prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is poured with the active ingredient preparation. You keep the The amount of water per unit area expediently constant. The active ingredient con Concentration in the preparation does not matter, only the effort is decisive amount of active ingredient per unit area.

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

It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, the compounds of the formula (I) according to the invention show strong Effect against weeds.  

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, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

The active ingredient preparation is used to inject test plants which are 5 - 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 2000 l water / ha the desired amounts of active ingredient are applied.

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

It means:
0% no effect (like untreated control)
100% total annihilation

In this test, the compounds of the formula (I) according to the invention show strong Effect against weeds.

Claims (9)

1. Substituted arysulfonylamino (thio) carbonyltriazolin- (thi) one of the general formula (I), in which
Ar represents optionally substituted arylene or heteroarylene,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R1 represents hydrogen, hydroxyl, amino, alkylidene amino or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,
R² for hydrogen, hydroxy, mercapto, amino, halogen or for an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkyl thio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, alkanoylamino , Aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, aryloxy, arylthio, arylamino, arylthoxy, arylthoxy, arylthoxy, arylalkyloxy or
R¹ and R² together represent optionally branched alkanediyl, and
R³ represents optionally substituted heterocyclyl,
and salts of the compounds of formula (I). 2. Compounds of formula (I) according to claim 1, characterized in that therein
Ar for each optionally by halogen, cyano, nitro, by C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁- C₄-alkylsulfonyl, di- (C₁-C₄-alkyl ) -amino-sulfonyl or N-C₁-C₄-alkoxy-N-C₁-C₄-alkyl-amino-sulfonyl (which are optionally substituted by fluorine and / or chlorine) substituted phenylene or naphthylene, or for optionally by halogen, Cyano, nitro, by C₁-C₄-alkyl or C₁-C₄-alkoxy (which are each optionally substituted by fluorine and / or chlorine) is a heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally are one or two more nitrogen,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for hydrogen, hydroxy, amino, for C₂-C₁₀-alkylidene amino, for C₁- optionally substituted by fluorine, chlorine, bromine, cyano, C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxy-carbonyl C₆-alkyl, for each optionally substituted by fluorine, chlorine and / or bromine, C₂-C₆-alkenyl or C₂-C₆-alkynyl, for each optionally by fluorine, chlorine, cyano, C₁-C₄-alkoxy or C₁-C₄-alkoxy- carbonyl substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino or C₁-C₆-alkanoylamino, for C₃-C₆-alkenyloxy, for di- (C₁-C₄-alkyl) -amino, each optionally with fluorine, chlorine, bromine, Cyano and / or C₁-C₄-alkyl substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, or for each optionally by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, trifluoromethyl and / or C₁-C₄-alkoxy substituted phenyl or phenyl-C₁-C₄- alkyl,
R² for hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, iodine, for optionally by fluorine, chlorine, bromine, cyano, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl or C₁-C₄alkoxycarbonyl Substituted C₁-C₆-alkyl, for each optionally substituted by fluorine, chlorine and / or bromine substituted C₂-C₆-alkenyl or C₂-C₆-alkynyl, each optionally substituted by fluorine, chlorine, cyano, C₁-C₄-alkoxy or C₁- C₄-Alkoxy-carbonyl substituted C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or C₁-C₆-alkanoylamino, for C₂- C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-alkenylthio, C₂ -C₆- alkynylthio, C₂-C₆-alkenylamino or C₂-C₆-alkynylamino, for di- (C₁-C₄-alkyl) -amino, for aziridino, pyrrolidino, piperidino or morpholino, each optionally substituted by methyl and / or ethyl C₃-C₆-cycloalkyl, C₅- C₆- optionally substituted by fluorine, chlorine, bromine, cyano and / or C₁-C₄-alkyl Cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cyclo alkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl -C₁-C₄-alkylthio or C₃-C₆- cycloalkyl-C₁-C₄-alkylamino, or for each optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, trifluoromethyl and / or C₁-C₄-alkoxy substituted phenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio, phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or for each optionally by fluorine, chlorine , Bromine, cyano, nitro, C₁-C₄-alkyl, trifluoromethyl and / or C₁-C₄-alkoxy substituted heterocyclyloxy or heterocyclylthio, where in each case the heterocyclyl component from the series oxiranyl, oxetanyl, furyl, tetrahydrofuryl, thietanyl, thienyl, thienyl is selected, or
R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and
R³ represents oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetrahydrothienyl which is optionally substituted by halogen or C₁-C₄alkyl,
as well as the sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di- (C₁-C₄-alkyl) -ammonium-, tri- (C₁-C₄-alkyl) -ammo nium-, tetra- (C₁-C₄-alkyl) -ammonium-, tri- (C₁-C₄-alkyl) -sulfonium-, C₅- or C₆-cycloalkyl-ammonium- and di- (C₁-C₂-alkyl) -benzyl -ammonium salts of compounds of formula (I). 3. Compounds of formula (I) according to claim 1, characterized in that therein
Ar for 1,2-phenylene (ortho-phenylene), which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio or ethylthio ), Pyridine-2,3-diyl, thiophen-2,3-diyl or pyrazole-4,5-diyl,
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for hydrogen, hydroxy, amino, for C₃-C₈-alkylideneamino, for each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, n-, i., Each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy -, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyloxy or butenyloxy, for dimethylamino or diethylamino, each optionally with fluorine, Chlorine, methyl and / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for phenyl or benzyl which is optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy
R² for hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or substituted by fluorine, chlorine, cyano, methoxy or ethoxy t-butyl, for propenyl, butenyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, i-, 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, for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, for dimethylamino, diethylamino or dipropylamino, for each optionally by fluorine, chlorine / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycl o pentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclo pentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclo pentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethylmethyl, cyclo butyl methyl methyl, cyclo butyl methyl methyl, cyclo butyl methyl, cyclo Cyclopropylmethylthio, Cyclobutylmethylthio, Cyclo pentylmethylthio, Cyclohexylmethylthio, Cyclopropylmethylamino, Cyclobutylmethylamino, Cyclopentylmethylamino or Cyclohexyl methylamino, or for phenyl, benzyl, phenyl, benzyl, phenyl, benzyl, phenyl, benzyl, phenyl, benzyl, benzyl, phenyl, benzyl, benzyl, phenyl, benzyl, phenyl, benzyl, phenyl, benzyl, benzyl, benzyl stands, or for oxetanyloxy, furyloxy, tetrahydrofuryloxy, thienyloxy or tetrahydrothienyloxy optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy, or
R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and
R³ represents in each case optionally substituted by fluorine, chlorine, methyl or ethyl oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl or tetrahydrothienyl. 4. Compounds of formula (Ia) in which
Q¹, Q², R¹, R² and R³ have the meanings given in Claim 3. 5. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

• (a) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given in Claim 1,
  with substituted arylsulfonyliso (thio) cyanates of the general formula (III) R³-O-CO-Ar-SO₂-N = C = Q² (III) in which
  Ar, Q² and R³ have the meanings given in Claim 1,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  or that one
• (b) triazolin (thi) on derivatives of the general formula (IV) in which
  Q¹, Q², R¹ and R² have the meanings given above and
  Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  with sulfonic acid amides of the general formula (V) R³-O-CO-Ar-SO₂-NH₂ (V) in which
  Ar and R³ have the meanings given above,
  if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
  or that one
• (c) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given above,
  with substituted arylsulfonic acid amide derivatives of the general formula (VI) R³-O-CO-Ar-SO₂-NH-CQ²-Z (VI) in which
  Ar, Q² and R³ have the meanings given above and
  Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
  or that one
• (d) triazolin (thi) one of the general formula (II) in which
  Q¹, R¹ and R² have the meanings given above,
  with substituted arylsulfonic acid halides of the general formula (VII) R³-O-CO-Ar-SO₂-X (VII) in which
  Ar and R³ have the meanings given above and
  X represents halogen,
  and metal (thio) cyanates of the general formula (VIII) MQ²CN (VIII) in which
  Q² has the meaning given above and
  M represents an alkali metal or an alkaline earth metal equivalent,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  and optionally the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are converted into salts by customary methods.

6. Herbicidal agents, characterized by a content of at least one A compound of formula (I) or one of its salts according to claim 1. 7. Use of compounds of general formula (I) or their Salts according to claim 1 for combating undesirable plants growth. 8. A method of combating weeds, characterized in that compounds of the general formula (I) or their salts according to Claim 1 can act on the weeds or their habitat.   9. A process for the preparation of herbicidal compositions, characterized in that that compounds according to general formula (I) or their salts Claim 1 with extenders and / or surfactants mixes.