EP2205091A2 - Salts of 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)carbamoyl]benzenesulfonamide, method for the production thereof and use thereof as herbicides and plant growth regulators - Google Patents

Abstract

The invention relates to salts of 2-iodo-N-[(4-methoxy-6-methyl-1,3,5-triazine-2- yl)carbamoyl]benzenesulfonamide, to methods for the production thereof, and use thereof as herbicides, in particular as herbicides for selectively combating undesired harmful plants in useful plant cultures, permanent crops or uncultivated land, and as plant growth regulators, by themselves, or with safeners and/or combined with other herbicides, use thereof for combating undesired harmful plants (such as unwanted grasses and weeds) in specific plant cultures or as plant protection regulators, with simultaneous and/or sequential use, either as a finished formulation or as a tank mix.

Description

 Salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide, process for their preparation, and their use as herbicides and plant growth regulators

description

This invention relates to salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide, to a process for their preparation and to their use as herbicides, in particular as Herbicides for the selective control of undesired weed plants in crops, permanent crops or non-crops, as well as plant growth regulators alone, or with safeners and / or in combination with other herbicides, their use for controlling unwanted weeds (such as weeds / grass weeds) in specific crops or known as crop protection regulators is, with simultaneous and / or sequential application, either as a ready-made formulation or as a tank mix.

It is known that substituted phenylsulfonylureas have herbicidal properties. These are e.g. phenyl derivatives which are monosubstituted or polysubstituted (for example US 4127405, WO 9209608, BE 853374, WO 9213845, EP 84020, WO 9406778, WO 02072560, US 4169719, US 4629494, DE 4038430). From WO 2006/114220 it is furthermore known that sulphonamides iodinated on the phenyl ring have herbicidal properties.

Surprisingly, it has now been found that salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide are particularly advantageously suitable as herbicides and / or plant growth regulators ,

The present invention thus provides agrochemically active salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide. The preferred subject matter of the present invention are compounds of the general formula (I)

where the cation (M ⁺ ) (a) is an ion of the alkali metals, preferably lithium, sodium, potassium, or

(b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group consisting of (C 1 -C 4) -alkyl, hydroxy (Cr

C ₄₎ alkyl, (C ₃ -C ₆₎ -cycloalkyl, (CrC ₄₎ alkoxy (Ci-C ₄₎ alkyl, hydroxy (CrC ₄₎ alkoxy (Ci-C4) alkyl, ( C ₁ -C ₆ ) -mercaptoalkyl, phenyl or benzyl, where the abovementioned radicals are optionally substituted by one or more identical or different radicals from the group consisting of halogen, such as F, Cl, Br or I, nitro, cyano, azido, ( C _r C ₆ ) alkyl, (C _r C ₆ ) haloalkyl, (C ₃ -C ₆ ) cycloalkyl, (CrC ₆ ) alkoxy, (C _r C ₆ ) haloalkoxy and phenyl are substituted, and wherein each if appropriate, two substituents on the N atom together form an unsubstituted or substituted ring, or

(e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C 1 -C ₄ ) alkyl) sulfonium, or (g) an oxonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) -oxonium, or (h) a saturated or unsaturated / aromatic N-, optionally mono- or polysubstituted and / or (C 1 -C ₄ ) -alkyl-substituted containing heterocyclic ionic compound having 1-10 C atoms in the ring system.

Further preferred are compounds of the formula (I) in which the cation (M ⁺ )

(a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

(b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or (d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group CJ) -alkyl, hydroxy- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) -alkoxy- (C ₁ -C ₂ ) -alkyl, hydroxy- ( CrC ₂ ) alkoxy- (Ci-C ₂ ) -alkyl, (dC ₂ ) -Mercaptoalkyl, phenyl or benzyl are substituted, the aforementioned

Radicals optionally substituted by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (dC ^ alkyl, (C _r C ₂₎ -haloalkyl, (C ₃ - C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) -alkoxy, (C _r C ₂ ) -haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-

Atom together, if appropriate, form an unsubstituted or substituted ring, or

(e) a quaternary phosphonium ion, preferably tetra - _((Ci-C4) - alkyl) phosphonium and tetraphenyl phosphonium, wherein the (CrC ₄₎ alkyl radicals and phenyl radicals optionally monosubstituted or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I, (C _r C ₂ ) -alkyl, (CrC ₂ ) - Haloalkyl, (C ₃ -C ₄₎ -cycloalkyl, (C _r C ₂₎ alkoxy, and (CrC ₂₎ - haloalkoxy substituted, or (T) is a tertiary sulfonium ion, preferably Ti - ((CrC ₄₎ -akyl ) - sulfonium or triphenyl-sulfonium, where the (C 1 -C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, such as F, Cl, Br or I, (C 1 -C ₂ ) -alkyl, ( C _r C ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (dC ₂ ) -alkoxy and (CrC ₂ ) -haloalkoxy, or (g) a tertiary oxonium ion, preferably tri - ((CrC ₄ ) -alkyl) - oxonium, where the (C _r C ₄ ) -alkyl radicals optionally mono- or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I, (C _r C ₂ ) -alkyl, (C ₁ -C ₂ ) - haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (C _r C ₂ ) alkoxy and (CrC ₂ ) - haloalkoxy substituted, or

(h) a cation from the series of the following heterocyclic compounds, such as pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5 Ethyl 2-methylpyridine, piperidine, pyrrolidine, morpholine,

Thiomorpholine, pyrrole, imidazole, 1, 5-diazabicyclo [4.3.0] non-5-ene

(DBN), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).

Preferred are compounds of formula (I) wherein the cation (M ⁺ ) is a sodium ion, a potassium ion, a lithium ion, a magnesium ion, a calcium ion, an NH ₄ ⁺ ion (2-hydroxyeth-1-yl) ammonium ion, bis-N, N- (2-hydroxyeth-1-yl) ammonium ion, tris-N, N, N- (2-hydroxyeth-1-yl) ammonium -lon, a methylammonium ion, a dimethylammonium ion, a trimethylammonium clay, a tetramethylammonium ion, an ethylammonium ion, a diethylammonium ion, a triethylammonium ion, a tretraethylammonium ion, an isopropylammonium ion, a diisopropylammonium ion , a tetrapropylammonium ion, a tetrabutylammonium ion Ion, a 2- (2-hydroxyeth-1-oxy) eth-1-yl ammonium ion, a di (2-hydroxyeth-1-yl) ammonium ion, a trimethylbenzylammonium ion, a tri ( (C 1 -C ₄ ) -alkyl) sulfonium ion, or a tri ((C 1 -C ₄ ) -alkyl) oxonium ion, a benzylammonium ion, a 1-phenylethylammonium ion, a 2-phenylethylammonium ion, a diisopropylethylammonium ion, a pyridinium ion, a piperidinium ion

Imidazolium ion, a morpholinium ion, a 1,8-diazabicyclo [5.4.0] undec-7-enium-ion.

Further preferred are compounds of formula (I) in which the cation (M ⁺ ) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, or an NH ₄ ⁺ ion.

Particular preference is given to compounds of the formula (I) in which the cation (M ⁺ ) is a sodium ion, a potassium ion or an NH ₄ ⁺ ion.

Very particular preference is given to compounds of the formula (I) in which the cation (M ⁺ ) is a sodium ion or a potassium ion.

In formula (I) and all subsequent formulas, the carbon-containing radicals such as alkyl, alkoxy may each be straight-chain or branched, e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.

Cycloalkyl means a carbocyclic saturated ring system preferably having 3-6 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Depending on the nature and linkage of the substituents, the compounds of the formula (I) can exist as stereoisomers. The possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). For example, if one or more alkenyl groups are present, then

Diastereomers (Z and E isomers) occur. For example, if one or more asymmetric carbon atoms are present, then enantiomers and Diastereomers occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which comprises the general formula (I), but are no longer specified with their specific stereoform, and their mixtures.

The preceding examples of radicals or ranges of radicals which fall under the general terms such as "alkyl" are not exhaustive. The general terms also include the definitions given below for residue regions in groups of preferred compounds, in particular residue regions which comprise specific residues from the table examples.

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 remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.

The present invention also provides processes for the preparation of the salts according to the invention, in particular of compounds of the general formula (I).

where you are

a) 2-iodobenzenesulfonamide (II)

with a heterocyclic carbamate of the formula (IM) H

/ γ ^N γγ ^CH 3 (III)

OCH,

wherein R * is a substituted or unsubstituted (CrC ₂ O) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C _{r C4)} alkyl,

implements, or

b) a sulfonylcarbamate of the formula (IV)

wherein R ** is a substituted or unsubstituted (CrC ₂ O) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (Ci-C ₄₎ -alkyl,

with a 2-amino-4-methoxy-6-methyl-triazine of the formula (V)

implements, or

c) 2-iodobenzenesulfonic acid isocyanate (VI)

with the aminoheterocycle of formula (V), or

d) 2-iodobenzenesulfonamide (II) with the isocyanate (VII)

^{> N} γ ^N γ ^CH 3 (VII)

OCH,

in the presence of a base, or

e) the base heterocycle of formula (V) is first base catalysed with a carbonic acid ester, e.g. Diphenyl carbonate, reacted and the intermediate formed in a one-pot reaction with 2-iodobenzenesulfonamide (II) (see variant a)) (see JP1989221366), or

f) a 2-iodobenzenesulfonic acid halide of the formula (VIII)

wherein Hal is a halogen atom, preferably chlorine (Villa), or fluorine (VIIIb), or bromine (VIIIc), with a cyanate, for example a metal cyanate, in particular an alkali metal cyanate, such as sodium cyanate, to the isocyanate of the formula (VI) or a solvated ( stabilized) derivative thereof, and then reacted with the amino heterocycle of formula (V) implements,

g) 2-iodobenzenesulphonamide (II) with a heterocyclic biscarbamate of the formula

(IIIa)

wherein R * is a substituted or unsubstituted (C ₁ -C _{2 0} ) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl (see WO 96/22284),

h) 2-iodobenzenesulfonamide (II) initially base catalysed with a

Carbonic acid esters, e.g. Diphenylcarbamat, and the intermediate formed in a one-pot reaction with the amino heterocycle of the formula (V)

(see variant b)).

The reaction of the compounds of the formulas (II) and (III) according to variant a) is preferably carried out under base catalysis in an inert organic solvent such as dichloromethane, acetonitrile, dioxane or THF at temperatures between 0 ⁰ C and the boiling point of the solvent, preferably at room temperature , Examples of bases used here are organic amine bases, such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), alkali tert-butoxide, such as, for example, NaO tert.-butylate, or alkali metal hydroxides, such as, for example, NaOH , especially when R * = (substituted) phenyl (see EP-A-44 807), or trialkylaluminum such as trimethylaluminum or triethylaluminum, the latter in particular when R ^* = alkyl (see EP-A-166 516) used. The particular base is used, for example, in the range of 1 to 3 molar equivalents, based on the compound of the formula (II). 2-iodobenzenesulfonyl isocyanate is a novel compound which, as well as its preparation and its use for the preparation of compounds of formula (I), are the subject of the present invention.

2-iodobenzenesulfonamide (II) can be e.g. as shown in the following Schemes 1 to 7.

Scheme 1

butyl

(IX) (IXa) (X)

Starting from the commercially available 2-nitroaniline (IX) can, for example by diazotization of the amino group with an alkali metal nitrite, such as. As sodium nitrite, in the presence of hydrochloric acid at temperatures between -1O ⁰ C and 10 ⁰ C and subsequent exchange of the resulting diazo z. B. with sulfur dioxide in the presence of a diluent, such as. For example, dichloromethane, 1, 2-dichloroethane or acetic acid, and in the presence of a catalyst such. As copper (l) chloride and / or copper (II) chloride, at temperatures between -1O ⁰ C and 5O ⁰ C 2- nitrobenzenesulfonyl chloride (IXa) are obtained (see Meerwein, Chem. Ber 1957, 90, 841) (Scheme 1). As an alternative to the use of sulfur dioxide, Na ₂ S ₂ O ₅ (sodium metabisulfite) can also be used as SO ₂ source.

By treating (IXa) with tert-butylamine, N-tert-butyl-2-nitrobenzenesulfonamide (X) can be obtained. The sulfonamide is, for example, in inert solvents such as dichloromethane, tetrahydrofuran (THF), dioxane, toluene or dimethylformamide (DMF) at temperatures between -70 ⁰ C to the boiling point of the solvent used, preferably carried out at 25 ⁰ C. In this case, preference is given to using an amine of from 1.5 to 2.5 equivalents, based on the sulfonyl chloride used. Scheme 2

The reduction of (X) to N-tert-butyl-2-aminobenzenesulfonamide (XI) is carried out analogously to known methods (cf., for this purpose, Houben-Weyl, "Methoden der Organischen Chemie", 4th ed., Vol. XI / 1 S 360 ff., Thieme Verlag Stuttgart, 1957) (Scheme 2).

Scheme 3

Aniline (XI) can be diazotised under standard conditions for diazotization reactions and then converted into N-tert-butyl-2-iodobenzenesulfonamide (XII). For example, the diazotization takes place in the presence of the acid H ⁺ X ^" , where X ^{" is} preferably Cl ^" , I ^" or HSO ₄ ^" , in aqueous solution, if appropriate using an organic solvent which is inert under the reaction conditions, with a nitrite an alkali metal nitrite such as NaNO ₂ (sodium nitrite) in amounts of from 1.0 to 1.2 mol of nitrite, preferably from 0.01 to 1.05 mol of nitrite, per mole of aniline (XI) Suitable acids are mineral acids or strong organic acids, preferably hydrochloric acid or sulfuric acid. the solvent is water or a mixture of water and an inert organic solvent under the reaction conditions. the reaction temperature is generally between -5 ⁰ C and 5O ⁰ C, preferably 1O ⁰ C to 2O ⁰ C. The reaction of the diazonium salts obtained for iodine compound (XII) is usually carried out without isolation and is carried out in the same aqueous or aqueous-organic solvent or solvent mixture as the diazotization. In the reaction, the diazonium group is replaced by the iodine atom, either by the anion of the diazonium salt (when X ^" = I ^" in the acid) or (if X is ^" not I ^" ) by the reaction with added iodide, e.g. For example, alkali metal iodide, preferably sodium iodide or potassium iodide. The amount of iodide is, for example, 1.1 to 1.5 moles of iodide per mole of originally used aniline (XI). The reaction temperature amounts to here generally 1O ⁰ C to 4O ⁰ C, preferably 15 ⁰ C to 3O ⁰ C (see. This example, DE 19625831 and Bioorg. Med. Chem. 2004, 12, 2079) (Scheme 3).

Scheme 4

(XII) (H)

The cleavage of the tert-butyl protecting group in (XII) to give 2-iodobenzenesulfonamide (II) takes place, for example, by treatment with a strong acid (see WO 89/10921). Examples of strong acids are mineral acids, such as H ₂ SO ₄ or HCl, or strong organic acids, such as trifluoroacetic acid. The reaction takes place for example at temperatures from -20 ⁰ C to the respective reflux temperature of the reaction mixture, preferably at ⁰ C to 40 ⁰ C. The reaction can be in bulk or in an inert solvent such as dichloromethane or trichloromethane, are carried out (Scheme 4). Scheme 5

N-tert-butyl-2-iodobenzenesulfonic acid amide (XII) can also be obtained by reacting N-tert-butyl-benzenesulfonic acid amide (XIV), which is prepared by reacting commercially available benzenesulfonyl chloride (XIII) with tert-butylamine (see Scheme 1) can be obtained with an organometallic compound, such as alkyl or aryllithium, preferably π- or sec-butyllithium in hexane, optionally in the presence of a (further) inert diluent, such as tetrahydrofuran, and under an inert gas atmosphere, such as under argon or nitrogen, at temperatures between -70 ⁰ C and 2O ⁰ C metallated - ie replaced in (XIV) in ortho position to Sθ ₂ NH-tert-butyl group replaced by a metal atom - and then in the same reaction medium with iodine at temperatures between -100 ⁰ C and 4O ⁰ C, preferably between -7O ⁰ C and 2O ⁰ C, whereby the metal atom is replaced by iodine (Scheme 5) is (see also: V. Snieckus et al., J. Org. Chem. 200 1, 66, 3662 and Synlett 2000, (9), 1294).

(XV) (Villa) (»)

2-iodobenzenesulfonamide (II) can also be obtained (Scheme 6) by dissolving 2-iodobenzenesulfonyl chloride (Villa) by diazotizing the amino group in 2-iodoaniline (XV) and then replacing the resulting diazo group with a chlorosulfonyl group (as in Scheme 1 described in more detail) is produced, reacted with ammonia. For this purpose, ammonia gas is introduced in inert solvent, preferably dichloromethane or tetrahydrofuran, until no more ammonia is absorbed.

Alternatively, 2-iodobenzenesulfonyl chloride (Villa) can also be converted to the N-tert-butyl-2-iodobenzenesulfonamide (XII) by reaction with tert-butylamine (analogous to Schemes 1 and 5). Subsequently, the tert-butyl protective group is then removed by means of acid (analogous to Scheme 4) to obtain 2-iodobenzenesulfonamide (II).

The sulfonylcarbamates of the general formula (IV) are prepared analogously to reactions known per se (cf EP-A-120 814). One can e.g. also

2-iodobenzenesulfonyl isocyanate of the formula (VI) in a smooth reaction in an inert solvent, preferably diethyl ether or dichloromethane with phenol in the carbamate of formula (IV) convert. The aminoheterocycles of formula (V) are known, in part commercially available synthetic chemicals. The reaction of the sulfonylcarbamates of the formula (IV) with the aminoheterocycles of the formula (V) is carried out by known processes (cf., for example, WO 2003 091228) (Scheme 7).

Scheme 7

2-iodobenzenesulfonyl isocyanate of the formula (VI) is a novel compound and is therefore also the subject of this invention. It can be prepared by processes known per se from 2-iodobenzenesulfonamide (II) (cf., DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504). The sulfonyl isocyanate of the formula (VI) is obtained when 2-iodobenzenesulfonamide (II) with phosgene, diphosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as butyl isocyanate, optionally in the presence of a reaction auxiliary, such as a tertiary amine, preferably a diazabicyclo [2.2.2] octane, and in the presence of a Verdünnungsmiteis, such as toluene, XyIoI or chlorobenzene, at temperatures between 80 ⁰ C and 150 ⁰ C reacted and after the completion of the reaction, if appropriate, the volatile components distilled off under reduced pressure (Scheme 8 ).

Scheme 8

("I) (VI)

The reaction of 2-iodobenzenesulfonyl isocyanates of the formula (VI) with the aminotriazine of the formula (V) is carried out, for example. by known processes (see WO 2003 091228) (Scheme 9).

Scheme 9

The isocyanates of the general formula (VII) are obtained, for example, from the aminoheterocycles of the type (V) by treatment with oxalyl chloride or phosgene (in analogy to Angew. Chem. 1971, 83, p. 407, EP 388 873). The reaction of the isocyanate of type (VII) with 2-iodobenzenesulfonamide (II) takes place, for example, in analogy to variant c) (Scheme 10). Scheme 10

2-iodobenzenesulphonic acid fluoride (VIIIb) can be prepared by various methods known from the literature: i) from 2-iodobenzenesulphonamide (II) by diazotization with alkali metal nitrite, for example sodium nitrite, and subsequent reaction with hydrogen fluoride (J.Am.Chem. Soc. 1951, 73, 1857 ); ii) reaction of 2-iodobenzenesulfonyl chloride (Villa) with potassium fluoride (J. Chem. Soc, Perkin Trans. 1, 1998, 5, 875); iii) Reaction of 2-iodobenzenesulfonic acid (XVII) with fluorosulfonic acid (US 2686202). 2-iodobenzenesulfonic acid bromide (VIIIc) can be synthesized, for example, by reaction of 2-iodobenzenesulfonyl chloride (Villa) with hydrogen bromide in acetic acid (Dokl. Akad. Nauk SSR 1955, 103, 627).

In one embodiment of variant f), the reaction mixture obtained by reaction of the sulfonic acid halide (VIII) with a cyanate is used directly for the coupling with the aminotriazine of the formula (V) for the synthesis of the precursor (neutral compound) of the formula (I) (cf. WO 2003 091228 and US 5550238).

The salts according to the invention, in particular those of the formula (I), can be selected from the neutral form of the sulphonylurea or sulphonylurea metal salts, in particular alkali metal salts (see for example EP-A-30138, EP-A-7687) or also starting from sulphonamide salts e.g. in the following way:

1. Deprotonation of the neutral sulfonylurea (XX) with a suitable base of the formula M ⁺ B ^" (Scheme 11), where B ^{" is} for example hydride, hydroxy or Alkoxy anions, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy or t-butoxy.

Scheme 11

For this purpose, the sulfonylurea of the formula (I) is dissolved or suspended in an inert solvent or solvent mixture and reacted with one equivalent of M ⁺ B ^" at temperatures between -2O ⁰ C and 100 ⁰ C, preferably between -10 ⁰ C and 5O ⁰ C. ,

2. Salification of metal salts of the sulfonylurea of the formula (Ia) in which Met ^{+ is} a metal cation, preferably an alkali metal ion such as Na ⁺ or K ⁺ , with suitable reagents of the formula M ⁺ X ^' (Scheme 12), where M ^{+ is} an ammonium ion and X ^{'may be} an anion, for example a halo anion such as F ^' , Cl ^" or Br ^' , or may be a phosphate, sulfate or carboxylate anion, which definition includes inorganic and organic salts, as used, for example, in surfactant chemistry (eg, organic phosphate anions, phosphonate anions, sulfate anions, sulfonate anions, carboxylates).

For this purpose, the metal salts of the invention, for. B. alkali salts (eg Met ⁺ = Na ⁺ , K ⁺ ) of the sulfonylurea dissolved in an inert solvent or solvent mixture and reacted with one equivalent of the reagent M ⁺ X ^' . After completion of the reaction by filtration, the by-product salt, z. For example, alkali metal salt (such as NaCl) are separated.

3. In situ deprotonation and resalting (Scheme 13) starting from the neutal sulfonylurea (XX) with suitable reagents a) of the formula M ⁺ X ^' , where M ^{+ is} an ammonium ion and X ^"is an anion, for example, a haloanion such as F ^" , Cl ^" or Br ^' or may be a phosphate, sulfate or carboxylate anion, this definition including inorganic as well as organic salts, such as are commonly used in surfactant chemistry (eg organic phosphate anions, phosphonate anions, sulfate anions, Sulfonate anions, carboxylates) and b) of the formula Met ⁺ B ^" wherein Met ^{+ is} a metal cation, in particular an alkali metal cation such as Na ⁺ or K ⁺ and B ^{" is} a suitable base, for example a hydroxy or alkoxy anion such as methoxy, ethoxy , n-propoxy, / -propoxy or n-butoxy or the anion of an alkoxylated, eg ethoxylated or propoxylated, (Ca-C ₄ o) -alcohol.

Scheme 13

For this purpose, the neutral Sulfonalharnstoff (XX) is dissolved in an inert solvent or solvent mixture and reacted with one equivalent of the reagents M ⁺ X ^' and MetB. After completion of the reaction, the by-produced metal salt, in particular alkali metal salt (eg NaCl) can be separated off by filtration.

4. Reactions of the neutral sulfonylurea (XX) with suitable zwitterions, e.g. B. (Scheme 14) Scheme 14

where R is a (CrC ₂ o) -carbon radical such as (C 1 -C 4) -alkyl, R 'and R "are identical or different and are hydrogen or (C ₁ -C 30) -hydrocarbon radicals such as (C ₁ -C 10) -alkyl and m is an integer of 0 to 100. To this end, the neutral sulfonylurea (XX) is reacted with a zwitterionin, as indicated, for example, in Scheme 14, in an inert solvent such as methanol, tetrahydrofuran or methylene chloride or solvent mixture at temperatures between -2O ⁰ C and 100 ⁰ C, preferably -1O ⁰ C and 8O ⁰ C reacted in equimolar ratios.

5. Reaction of a sulfonic acid amide salt of the formula (IIa) with the isocyanate (VII) (Scheme 15).

Scheme 15

The reaction takes place in an inert solvent or solvent mixture - such as. B. tetrahydrofuran - at temperatures between -2O ⁰ C and 100 ⁰ C, preferably between -1O ⁰ C and 7O ⁰ C, by reacting the isocyanate (VII) equimolar with the sulfonic acid amide salt of the formula (IIa). In this case, the sulfonic acid amide salt of the formula (IIa) can be used directly or be formed in situ - z. By reaction of the corresponding sulfonic acid amide of formula (II) with a suitable base M ⁺ X ^" , where M ^{+ is} an ammonium ion and X ^'is, for example, a hydroxy or alkoxy anion.

6. Reaction of a sulfonic acid amide salt of the formula (IIa) with a carbamate of the general formula (III) (Scheme 16)

The reaction is carried out in an inert solvent (or solvent mixture) - such as tetrahydrofuran - at temperatures between -2O ⁰ C and 100 ⁰ C, preferably between -1O ⁰ C and 70 ⁰ C by reacting the carbamate of the formula (III) equimolar with with the sulfonic acid amide salt of the formula (IIa). In this case, the sulfonic acid amide salt of the formula (IIa) can be used directly or formed in situ - z. By reaction of the corresponding sulfonic acid amide with a suitable base M ⁺ X ^" , where M ^{+ is} an ammonium ion and X ^{" is} e.g. B. a hydroxy or alkoxy anion.

7. Reaction of the neutral sulfonylurea (XX) with a primary, secondary or tertiary amine NRR'R "(Scheme 17) wherein R, R 'and R" are the same or different radical selected from the group consisting of: (a) H .

(b) an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the group (C _{r C4)} alkyl, hydroxy (C _{r C4)} alkyl, ( C ₃ -C ₆ ) cycloalkyl, (C _r C ₄ ) alkoxy (Cr C ₄ ) alkyl, hydroxy (CrC ₄ ) alkoxy (CrC ₄ ) alkyl, (C _r C ₆ ) -Mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned radicals are optionally substituted by one or more, the same or various radicals from the group halogen, such as F, Cl, Br or I ₁ nitro, cyano, azido, (Ci-Cβ) - alkyl, (d-CeJ-haloalkyl, (C ₃ -C ₆ ) -cycloalkyl, (C _r C ₆ ) -alkoxy, (C ₁ -C ₆ ) -

Haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N atom together optionally form an unsubstituted, optionally a substituted ring, or

(C) a possibly singly or multiply fused and / or (C 1 -C ₄ ) alkyl substituted saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 carbon atoms in the ring system correspond

This reaction takes place between temperatures of -2O ⁰ C to 100 ⁰ C, preferably between -1O ⁰ C and 5O ⁰ C, in inert solvent, such as. As tetrahydrofuran, methylene chloride or methanol or mixtures of solvents instead.

By the term "inert solvents" denoted in the above process variants are meant in each case solvents which are inert under the respective reaction conditions, but need not be inert under any reaction conditions.

Collections of salts according to the invention, in particular those of the formula (I) which can be synthesized after the abovementioned reactions, can also be prepared in a parallelized manner, this being manual, in part automated or completely automated way. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood as an approach as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity:"

Automated Synthesis ", Volume 1, published by Escom 1997, pages 69 to 77.

For microwave assisted syntheses, a microwave oven, e.g. Model "Discover" by the company CEM GmbH Microwave Analysis, Carl-Friedrich-Gauss-Str. 9, 47475 Kamp-Lintfort be used.

For parallelized reaction performance and work-up, a variety of commercially available equipment can be used, such as those available from Stern Corporation, Woodrolfe Road, Tollesbury, Essex, England, H + P

Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany or the company Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England. For the parallelized purification of compounds of the general formula (I) or of intermediates obtained during the preparation, there are, inter alia, chromatography apparatuses

Available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems may be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA. In addition to the methods described here, the preparation of the salts according to the invention, in particular of compounds of the general formula (I), can be carried out completely or partially by methods supported by solid phases. For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin. Solid-phase assisted synthetic methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998.

The use of solid-phase assisted synthesis methods allows a number of protocols known from the literature, which in turn can be carried out manually or automatically. For example, the "teabag method" (Houghten, US 4,631,211; Houghten et al., Proc Natl Acad. Sei, 1985, 82, 5131-5135) can be used with products of IRORI, 11149 North Torrey Pines Road, La JoIIa , CA 92037, USA. The automation of solid-phase assisted parallel synthesis succeeds, for example, by equipment of the companies Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein provides the salts according to the invention, in particular compounds of the formula (I), in the form of substance collections called libraries. The present invention also provides libraries containing at least two compounds of the invention, in particular compounds of formula (I).

The salts according to the invention, in particular compounds of the formula (I), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It is It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence procedures.

If the salts according to the invention, in particular compounds of the formula (I), are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die after expiration from three to four weeks completely off. When the active ingredients are applied to the green parts of the plants postemergence, a drastic growth stop also occurs very rapidly after the treatment, and the weed plants remain in the position reached at the time of application

Growth stage or die completely after a certain time, so that in this way harmful to the crops weed competition is eliminated very early and sustainably.

Although the salts according to the invention, in particular the compounds of the formula (I), have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g. Wheat, barley, rye, oats, rice, maize, sugarcane, flax and other plantation crops are marginally or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.

Furthermore, the salts according to the invention, in particular compounds of the formula (I) have very advantageous properties with regard to the behavior in the environment, in particular with respect to the reproduction behavior, i. towards the compounds according to the invention of the formula (I) otherwise sensitive cultures, such as sugar beet, sunflower or Cruciferen, such as rapeseed, mustard and turnip rape.

Moreover, the salts according to the invention, in particular the compounds of the formula (I), have excellent growth-regulatory properties in crop plants. They regulate in the plant's own Metabolism and can thus be used for the targeted influencing of plant ingredients and to facilitate harvesting, such as by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.

Due to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known. Likewise, because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of known or yet to be developed mutant-selected plants.

Preference is given to the use of the salts according to the invention, in particular of compounds of the formula (I), in economically important transgenic or mutant-selected crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or even crops of rapeseed, potato, tomato, pea and other vegetables. Preferably, the salts according to the invention, in particular the compounds of the formula (I), can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant, or obtained by mutant selection. Likewise, the salts according to the invention, in particular the compounds of the formula (I), can likewise be used as herbicides in crops which represent a cross product of genetically resistant plants and plants obtained by mutant selection, as described, for example, in WO 2007/024782.

Well-known routes for the production of new plants which have modified properties compared to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.

Likewise, new plants with altered properties can be produced by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, in several cases, genetic modifications of cultivated plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which are resistant to certain glufosinate-type herbicides (US Pat. see, for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659), - transgenic crop plants, for example Cotton, with the ability

To produce Bacillus thuringiensis toxins (Bt toxins) which render the plants resistant to certain pests (EP-A-0142924, EP-A-

0193259). Transgenic crop plants with modified fatty acid composition (WO 91/13972). Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; See, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).

For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the aid of the abovementioned standard methods, z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments. The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. Also possible is the use of DNA sequences encoding a high degree of homology to the ones

Have sequences of a gene product but are not completely identical. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Be. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

The salts according to the invention, in particular compounds of the formula (I), can preferably be employed in transgenic or mutant-selected cultures or crosses / hybrids thereof which are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate isopropylammonium and analogous active substances.

In the application of the active compounds according to the invention in transgenic or mutant selection-derived cultures or crosses thereof, in addition to the effects observed in other cultures on harmful plants, effects which are specific for the application in the respective transgenic or mutant selection-derived cultures or crosses thereof are often present, For example, a modified or specially extended weed spectrum that can be controlled, changed application rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of transgenic crops. The invention therefore also relates to the use of the salts according to the invention, in particular of compounds of the formula (I), as herbicides for controlling harmful plants in transgenic or mutant-selected crop plants or crosses thereof. The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating agents which contain the compounds of the formula (I).

The salts according to the invention, in particular the compounds of the formula (I), can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water dispersible

Granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,

"Surface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix. Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,

Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, lignosulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonate sodium or oleoylmethyltaurine acid. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,

Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.

Polyoxyethylene.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding by means of commercial bead mills and, if appropriate, addition of surfactants, as already listed above, for example, in the other formulation types.

Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types. Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluid bed, extruder and spray granules, see e.g.

Process in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York,

1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. The agrochemical preparations generally contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, particularly preferably from 0.5 to 90% by weight of active ingredient of the salts according to the invention, in particular of the compounds of the formula (I) , In wettable powders, the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight. In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Suitable solid carriers are: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules: For example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: for example, lignin liquors and methylcellulose.

It can be used in the formulations adhesives such as carboxymethyl cellulose, natural and synthetic powdery, kömige or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural

Phospholipids such as cephalins and lecithins and synthetic phospholipids.

The herbicidal activity of the herbicidal combinations according to the invention may be e.g. also be improved by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers. The fatty alcohol

Polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether section. The fatty alcohol polyglycol ethers may be nonionic, or ionic, e.g. in the form of fatty alcohol polyglycol ether sulfates, e.g. as alkali salts (e.g., sodium and potassium salts) or ammonium salts, or as alkaline earth salts such as

Magnesium salts can be used, such as C ₂ / C ₄ fatty alcohol diglykolethersulfat- sodium (Genapol ^® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Nonionic fatty alcohol polyglycol ethers are, for example, 2 to 20, preferably 3 to 15,

Ethylene oxide units containing (do-Ci ₈ ) -, preferably (Ci ₀ -Ci ₄ ) fatty alcohol polyglycol ether (eg isotridecyl alcohol polyglycol ether), for example from the Genapol ^® X series such as Genapol ^® X-030, Genapol ^® X-060, Genapol ^® X-080 or Genapol ^® X-150 (all from Clariant GmbH).

The present invention further comprises the combination of components A and B with the previously mentioned wetting agents from the series of fatty alcohol Polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and may be present nonionically or ionically (for example as fatty alcohol polyglycol ether sulfates). 15 ethylene oxide units, for example from the Genapol ^® X series, such as Genapol ^® X-030, Genapol ^® X - C ₂ / Ci4-fatty alcohol diglycol ether sulfate sodium (Genapol ^® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3 are preferably 060, Genapol ^® X-080 and Genapol ^® X-150 (all from Clariant GmbH). It is also known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol Polyglykolethersulfate) as a penetration aid and enhancer for a number of other herbicides, including for

Herbicides from the series of imidazolinones are suitable (see for example EP-A-0502014).

Furthermore, it is known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol polyglycol ether) are also suitable as penetration aids and effect enhancers for a number of other herbicides, including for herbicides from the series of imidazolinones (see for example EP-A -0,502,014).

The herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils. The term vegetable oils refers to oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

The vegetable oils are preferably esters of C1 -C22- _0, preferably C12-C-20 fatty acids. The C _O -C ₂ 2-fatty acid ester are, for example, esters of unsaturated or saturated Cio-C ₂₂ fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C- | ₈ fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid. Examples of C ₁₀ -C ₂₂ fatty acid esters are esters obtained by reacting glycerol or glycol with the C _O -C ₂₂ fatty acids, as they are, for example, in oils from oil-plant species, or -C ₂ o alkyl -CioC22 fatty acid esters, as for example, by transesterification of the aforementioned glycerol or glycol Ci ₀ -C ₂₂ fatty acid esters with CrC ₂ o-alcohols (eg, methanol, ethanol, propanol or

Butanol) can be obtained. The transesterification can be carried out by known methods, such as e.g. are described in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.

Preferred as CrC ₂ o-alkyl-Cio-C ₂₂ fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters. Preferred glycol- and glycerol-Cio-C ₂₂ fatty acid esters the uniform or mixed Glykolester and Glycerinester of Cio-C ₂₂ fatty acids are preferred, in particular fatty acids having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C ₈ Fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

The vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ^® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ^® B (Novance, France, hereinafter called ActirobB, main ingredient: Rapsölmethylester), Rako-binol ^® (Bayer AG, Germany, referred to as Rako-binol called main constituent: rapeseed oil), Renol ^® (Stefes, Germany, termed Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ^® (Stefes , Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester) may be contained.

In a further embodiment, the present invention comprises combinations with the abovementioned vegetable oils, such as rapeseed oil, preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil, such as ^Hasten® (Victorian Chemical Company, Australia, below Hasten mentioned, main ingredient: rapeseed oil ethyl ester), Actirob ^® B (Novance, France, hereinafter ActirobB called Main Ingredient: (rapeseed oil), Renol ^®: Rapsölmethylester), Rako-Binol ^® (Bayer AG, Germany, termed Rako-Binol, main ingredient , hereinafter referred Stefes, Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ^® (Stefes, Germany, termed Mero called main ingredient: Rapsölmethylester).

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 salts according to the invention, in particular the compounds of the formula (I), can be used as such or in the form of their formulations (formulations) with other pesticide-active substances, such as. As insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, eg. B. as a ready-made formulation or as tank mixes.

Suitable combination partners for the salts according to the invention, in particular for the compounds of the formula (I) in mixture formulations or in a tank mix, are, for example, known, preferably herbicidal active ingredients which are based on inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase. Such compounds as well as other useful compounds with partially unknown or other mechanism of action are described, for example, in Weed Research 26, 441-445 (1986), or in the manual "The Pesticide Manual", 12th edition 2000, or 13th edition 2003 or 14. Edition 2006/2007, or in the corresponding "e-Pesticide Manual", Version 4 (2006), each published by the British Crop Protection Council, (hereinafter also referred to as "PM"), and literature cited there names "are The herbicides known from the literature which can be combined with the compounds of the formula (I) are, for example, the active ingredients listed below:

(Note: The herbicides are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical

Names, if appropriate together with a common code number, and always include all forms of application such as acids, salts, esters and isomers such as

Stereoisomers and optical isomers, in particular the commercial form or the commercially available forms, unless otherwise stated in the context. In the case of sulfonamides such as sulfonylureas, salts also include those which are formed by replacement of a hydrogen atom on the sulfonamide group by a cation. One and sometimes several

Called application forms): acetochlor; acibenzolar-S-methyl; acifluorfen (-sodium); aclonifen; AD-67; AKH 7088, i. [[[1 - [5- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-nitrophenyl] -

2-methoxyethylidene] amino] oxy] acetic acid and acetic acid methyl ester; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; ammonium pelargonate; AMS, i. ammonium sulfamate; ancimidol; anilofos; asulam; atrazine; aviglycine; azafenidin, azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516H, i. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide (UBH-509), benazoline (-ethyl); bencarbazone; benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzfendizone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac (-sodium) (KIH-2023); borax; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos; butenachlor (KH-218); buthidazole; butraline; butroxydim; butylate; cafenstrole (CH-900); caloxydim; carbetamide; carfentrazone (-ethyl); catechin; CDAA, i. 2-chloro-N, N-di-2-propenylacetamide; CDEC, i.

Diethyldithiocarbamic acid 2-chlorallylester; chlormesulone; chlomethoxyfen; chloramben; chlorazifop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorfenprop; chlorflurecol (-methyl); chlorflurenol (-methyl); chloridazon; chlorimuron (-ethyl); chlormequat (chlorides); chlornitrofen; chlorophthalim (MK-616); chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlorotoluron; cinidone (-methyl and -ethyl); cinmethylin; cinosulfuron; clefoxydim; clethodim; clodinafop and its ester derivatives (eg clodinafop-propargyl); clofencet; clomazone; clomeprop; cloprop; cloproxydim; clopyralid; clopyrasulfuron (- methyl); cloransulam (-methyl); cumyluron (JC 940); cyanamide; cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its

Ester derivatives (e.g., butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron;

2,4-D; 2,4-DB; dalapon; daminozide; dazomet; n-decanol; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichlormid; dichlorprop (-P) salts; diclofop and its esters such as diclofop-methyl; diclofop-P (methyl); diclosulam; diethatyl (-ethyl); difenoxuron; difenzoquat (-metilsulfate); diflufenican; diflufenzopyr (-sodium); dimefuron; dimepiperate; dimethachlor; dimethametryn; dimethazone; dimethenamid

(SAN-582H); dimethenamide-P; dimethylarsinic acid; dimethipin; dimetrasulfuron; dimexyflam; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.

5-cyano-1- (1, 1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; epoprodan; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethephon; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (e.g.

HN-252); ethoxysulfuron; etobenzanide (HW 52); F5231, i. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; fenchlorazole (-ethyl); fenclorim; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, e.g. fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide; fenuron; ferrous sulfate; flamprop (-methyl or -isopropyl or

-isopropyl-L); flamprop-M (-methyl or -isopropyl); flazasulfuron; floatsulate (JV-485); florasulam; fluazifop and fluazifop-P and their esters, eg fluazifop-butyl and fluazifop-P-butyl; fluazolate; flucarbazone (-sodium); flucetosulfuron; fluchloralin; flufenacet; flufenpyr (-ethyl); flumetralin; flumetsulam; flumeturon; flumiclorac (-pentyl); flumioxazine (S-482); flumipropyn; fluometuron; fluorochloridone; fluorodifen; fluoroglycofen (-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupropanoate; flupyrsulfuron (-methyl) (- sodium); flurenol (-butyl); fluridone; flurochloridone; fluroxypyr (-meptyl); fluφrimidol; flurtamone; fluthiacet (-methyl) (KIH-9201); fluthiamide; fluxofenim; fomesafen; foramsulfuron; forchlorfenuron; fosamine; furyloxyfen; gibberillic acid; glufosinate (-ammonium); glyphosate (- isopropylammonium); halo safen; halosulfuron (-methyl); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; HC-252; hexazinone; HNPC-C9908, ie, methyl 2 - [[[[[4-methoxy-6- (methylthio) -2-pyrimidinyl] amino] carbonyl] amino] sulfonyl] benzoate; imazamethabenz (-methyl); imazamox; imazapic; imazapyr; imazaquin and salts such as the ammonium salt; imazethapyr; imazosulfuron; inabenfide; indanofan; iodosulfuron-methyl (-sodium); ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole; isoxaflutole; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; Maleic hydrazide (MH); MBTA; MCPA; MCPB; mecoprop (-P); mefenacet; mefluidide; mepiquat (chlorides); mesosulfuron (- methyl); mesotrione; metam; metamifop; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methylarsonic acid; methyl-cyclopropene; methyldymron; methylisothiocyanate; methabenzthiazuron; metobenzuron; metobromuron; (Alpha-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; monosulfuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide, napropamide; naptalam; NC

310, i. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazol; neburon; nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrophenolate mixture; nitrofluorfen; nonanoic acid; norflurazon; orbencarb; orthosulfamuron; oxabetrinil; oryzalin; oxadiargyl

(RP-020630); oxadiazon; oxasulfuron; oxaziclomefone; oxyfluorfen; paclobutrazol; paraquat (dichlorides); pebulate; pelargonic acid; pendimethalin; penoxulam; pentachlorophenol; Pentanochlor; pentoxazone; perfluidone; pethoxamid; phenisopham; phenmedipham; picloram; picolinafen; pinoxaden; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); probenazole; procarbazone- (sodium); procyazine; prodi amines; profluralin; profoxydim; Prohexadione (-Calcium); prohydrojasmon; proglinazine (-ethyl); prometon; prometryne; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propoxycarbazone (-sodium) (MKH-6561); Propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil; pyraflufen (-ethyl)

(ET-751); pyrasulfotole; pyrazolynate; pyrazon; pyrazosulfuron (-ethyl); pyrazoxyfen; pyribambenz isopropyl (ZJ 0702); pyrimbenzopropyl (ZJ 0273); pyribenzoxim; pyributicarb; pyridafol; pyridate; pyriftalid; pyriminobac (-methyl) (KIH-6127); pyrimisulfan (KIH-5996); pyrithiobac (-sodium) (KIH-2031); pyroxasulfones (KIH-485); pyroxofop and its esters (eg propargyl esters); pyroxsulam; quinclorac; quinmerac; quinoclamine; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives eg quizalofop-ethyl; quizalofop-P-tefuryl and

ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i. 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; sintofen; SN 106279, i. 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] -propanoic acid and methyl ester; sulcotrione; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (-methyl); sulfosate

(ICI-A0224); sulfosulfuron; TCA (-sodium); tebutam (GCP-5544); tebuthiuron; tecnacene; tefuryltrione; tembotrione; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, i. N, N -diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1 H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thidiazuron; thiencarbazone (-methyl); thifensulfuron (-methyl); thiobencarb; Ti 35; tiocarbazil; topramezone; tralkoxydim; tri-allate; triasulfuron; triaziflam; triazofenamide; tribenuron (-methyl); triclopyr; tridiphane; trietazine; trifloxysulfuron (-sodium); trifluralin; triflusulfuron and esters (e.g., methyl esters, DPX

66037); trimeturon; trinexapac; tritosulfuron; tsitodef; Uniconazole; vernolate; WL

110547, i. 5-phenoxy-1- [3- (trifluoromethyl) -phenyl] -1H-tetrazole; D-489; ET-751;

KIH-218; KIH-485; KIH-509; KPP-300; LS 82-556; NC-324; NC-330; DPX-N8189;

SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; TH-547; SYN-523; IDH-100; SYP-249; HOK-201; IR 6396; MTB-951; NC 620th

Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the salts according to the invention, in particular the compounds of the formula (I) already have very good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle in some cultures and above all also in the case of mixtures with other herbicides which are less selective occur. In this regard are Combinations of salts according to the invention, in particular of compounds of the formula (I) of particular interest, which comprise the salts according to the invention, in particular the compounds of the formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.

The safeners are preferably selected from the group consisting of:

A) compounds of the formula (S-I),

where the symbols and indices have the following meanings: ΠA is a natural number from 0 to 5, preferably 0 to 3;

RA ¹ is halogen, (CrC ₄₎ alkyl, (dC ₄₎ -alkoxy, nitro or (C _r C ₄₎ -haloalkyl; WA is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero-ring atoms of the type N or O, at least one N-atom and at most one O-atom in the ring, preferably a radical from the group (W _A ¹ ) to (W _A ⁴ ),

(W _A 1) (WA ² ) (W _A ³ ) (W /) m _A is 0 or 1;

RA ² is ORA ³ , SR _A ³ or NR _A ³ R _A ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one

N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (SI) and is unsubstituted or substituted by radicals from the group (C 1 -C ₄ ) -alkyl, (C 1 -C ₄ ) -alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _A ³ , NHR _A ⁴ or N (CH ₃ ) _2> in particular of the formula OR _A ³ ; RA ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having in total 1 to 18 carbon atoms;

RA ⁴ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -alkoxy or substituted or unsubstituted phenyl;

RA ⁵ is H, (CrC ₈₎ alkyl, C _r C ₈ (haloalkyl), (Ci-C ₄₎ alkoxy (CrC ₈₎ -alkyl, cyano or COOR ^9, wherein R _A ⁹ is hydrogen, (C _r C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -

Alkoxy (Ci-C ₄₎ alkyl, (Ci-C ₆₎ hydroxyalkyl, _(C3-Ci2) -cycloalkyl or Tn (Cr _C4) -alkyl-silyl;

RA ⁶ , RA ⁷ , RA ⁸ are identical or different hydrogen, (C 1 -C ₈ ) -alkyl,

(C-ι-Ca) -haloalkyl, _(C3-Ci2) -cycloalkyl or substituted or unsubstituted phenyl;

preferably: a) compounds of the type dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1 ) ("Mefenpyr-diethyl", see Pestic. Man.), And related compounds as described in WO 91/07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1 -2), 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole 3-carboxylic acid ethyl ester (S1-3),

Ethyl 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylate (S1-4), 1- (2,4-dichlorophenyl) -5-phenyl-pyrazole 3-carboxylic acid ethyl ester (S1 -5) and related compounds as described in EP-A-333,131 and EP-A-269,806; c) compounds of the triazolecarboxylic acid type, preferably compounds such as fenchlorazole (ethyl ester), ie 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1, 2,4- triazole-3-carboxylic acid ethyl ester (S1-6), and related compounds as described in EP-A-174,562 and EP-A-346,620; d) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds such as 5- (2,4-) Dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1 -7) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) and related compounds, as described in WO 91/08202, or the 5th , 5-diphenyl-2-isoxazoline-carboxylic acid ethyl ester (S1-9) ("isoxadifen-ethyl") or n-propyl ester (S1-10) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline 3-Carbonsäureethylester (S1-11), as described in the patent application WO-A-95/07897.

B) quinoline derivatives of the formula (S-II),

(S-II) where the symbols and indices have the following meanings: RB ^{1 is} halogen, (dC ₄₎ alkyl, (C ₁ -C ₄ J -alkoxy, nitro or (C _r C ₄₎ -haloalkyl; n _B is a natural number from 0 to 5, preferably 0 to 3;

RB ² ORB ³ , SR _B ³ or NR ₈ ³ RB ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, via the N - Atom is connected to the carbonyl group in (S-II) and unsubstituted or by

Radicals from the group (C 1 -C ₄ ) -alkyl, (C 1 -C ₄ ) -alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB ³ , NHRB ⁴ or N (CH ₃ ) ₂ , in particular of the formula ORB ³ ;

RB ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;

RB ⁴ is hydrogen, (C 1 -C ₆ ) -alkyl, (C 1 -C ₆ ) -alkoxy or substituted or unsubstituted phenyl. TB is a (Ci or C ₂ ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C ₄ ) -alkyl radicals or by [(C ₁ -C ₃ ) -alkoxy] -carbonyl;

preferably: a) compounds of the 8-quinolinoxyacetic acid (S2) type, preferably

(5-Chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester (Common name

"Cloquintocet-mexyl" (S2-1) (see Pestic. Man.),

(5-chloro-8-quinolinoxy) acetic acid (1, 3-dimethylbut-1-yl) ester (S2-2),

(5-Chloro-8-quinolinoxy) acetic acid 4-allyl oxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy) acetic acid 1 -allyloxy-prop-2-yl ester (S2-4),

(5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),

(5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),

Allyl (5-chloro-8-quinolinoxy) acetates (S2-7),

(5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl-ester (S2-9) and related

Compounds as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-O

492,366, and their hydrates and salts as described in the WO-A-

2002/034048 are described. b) compounds of the (5-chloro-8-quinolinoxy) malonic acid type, preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate,

(5-chloro-8-quinolinoxy) malonate,

(5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.

C) Compounds of the formula (S-III)

where the symbols and indices have the following meanings: Rc ¹ is (C _{r C4)} alkyl, (C _{r C4)} -haloalkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ haloalkenyl, (C ₃ -C ₇ ) -cycloalkyl, preferably dichloromethyl; Rc ^2, rc ³ is identical or different hydrogen, (C _{r C4)} alkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ -alkynyl, (C _{r C4)} -haloalkyl, (C ₂ -C ₄₎ haloalkenyl, (dC ^ O-alkylcarbamoyl (Ci-C ₄₎ alkyl, (C ₂ -C ₄₎ -Alkenylcarbamoyl- (Ci-C ₄₎ alkyl, (C _{r C4)} alkoxy- _(Ci-C4) alkyl, dioxolanyl (Ci-C ₄₎ -alkyl, thiazolyl, furyl, furylalkyl, thienyl , Piperidyl, substituted or unsubstituted phenyl, or Rc ² and Rc ³ together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;

preferably: active agents of the dichloroacetamide type, often as pre-emergence safeners

(soil-active safeners) are used, such. B.

"Dichlormid" (see Pestic.Man.) (= N, N-diallyl-2,2-dichloroacetamide),

"R-29148" (= S-dichloroacetyl ^^. Δ-trimethyl-I .S-oxazolidine from Stauffer),

"R-28725" (= 3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine from Stauffer), "Benoxacor" (see Pestic. Man.) (= 4-dichloroacetyl-3,4-dihydro 3-methyl-2H-1,4-benzoxazine),

"PPG-1292" (= N-allyl-N-KI.S-dioxolane) -y-O-methyl-J-dichloroacetamide from the company

PPG Industries),

"DKA-24" (= N-allyl-N-kallylaminocarbonyO-methyll-dichloroacetamide from Sagro-Chem),

"AD-67" or "MON 4660" (= 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane from the

Company Nitrokemia or Monsanto),

"TI-35" (= 1-dichloroacetyl-azepane from TRI-Chemical RT)

"Diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (= 3-dichloroacetyl-2,5,5-trimethyl, 3-diazabicyclo [4.3.0] nonane from BASF) and

"Furilazole" or "MON 13900" (see Pestic. Man.) (= (RS) -3-dichloroacetyl-5- (2-furyl) -2,2-dimethyloxazolidine)

D) N-acylsulfonamides of the formula (S-IV) and their salts,

wherein

X ₀ is CH or N; R _D ¹ is CO-NRD ⁵ RD ⁶ or NHCO-R ₀ ⁷ ;

RD ² is halogen, (C _{r C4)} -haloalkyl, (Ci-C ₄₎ -haloalkoxy, nitro, (CrC ₄₎ alkyl, (C _{r C4)} alkoxy, (Ci-C ₄₎ alkylsulfonyl, (C 1 -C ₄ ) alkoxycarbonyl or (C 1 -C ₄ ) -alkylcarbonyl; R ₀ ³ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl or (C ₂ -C ₄ ) -alkynyl; R ₀ ⁴ is halogen, nitro, (C _{r C4)} alkyl, (C _{r C4)} -haloalkyl, (C _r C ₄₎ -haloalkoxy, (C ₃ - C ₆₎ cycloalkyl, phenyl, (CrC ₄ ) alkoxy, cyano, (C _{r C4)} alkylthio, (C _{r C4)} alkyl- sulfinyl, (C _r C ₄₎ alkylsulfonyl, (CrC ₄₎ -alkoxycarbonyl or (CrC ₄₎ alkylcarbonyl; R ₀ ⁵ is hydrogen, (C _r C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₂ -Ce) -alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₅ -C ₆ ) -Cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing V ₀ heteroatoms from the group nitrogen, oxygen and sulfur, wherein the seven latter radicals by VD substituents selected from the group consisting of halogen, (Cr C ₆ ) alkoxy, (CrC ₆₎ -haloalkoxy, (C _r C ₂₎ alkylsulfinyl, (C _r C ₂₎ alkylsulfonyl, (C ₃ -C ₆₎ - cycloalkyl, (C _{r C4)} alkoxycarbonyl, (C _{r C4)} alkylcarbonyl and phenyl and in the case of cyclic radicals also (C _r C ₄ ) -alkyl and (CrC ₄ ) -haloalkyl are substituted;

R ₀ ⁶ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl or (C ₂ -C ₆ ) -alkynyl, where the last three radicals mentioned are represented by VD radicals from the group consisting of halogen, hydroxy, (Cr C ₄ ) alkyl, (dC ₄ ) alkoxy and (dC ₄ ) alkylthio substituted, or

RD ⁵ and RD ⁶ together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

RD ⁷ is hydrogen, (C 1 -C ₄ ) -alkylamino, di- (C ₁ -C ₄ ) -alkylamino, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, where the 2 last-mentioned radicals are represented by VD substituents from the group Group halogen, (Ci-C ₄ ) alkoxy, halogen (CrC ₆ ) alkoxy and (CrC ₄ ) alkylthio and in the case of cyclic radicals are also (Ci-C ₄ ) alkyl and (CrC ₄ ) haloalkyl substituted ;

n _D is 0, 1 or 2; m _D is 1 or 2;

V ₀ is 0, 1, 2 or 3;

preferred are compounds of the type of N-acylsulfonamides, e.g. the following formula (S-V), the z. B. are known from WO 97/45016

wherein

RD ⁷ (Ci-Cβ) alkyl, (C ₃ -C ₆ ) cycloalkyl, where the 2 latter radicals by VD

Substituents from the group halogen, (C ₁ -C ₄ ) alkoxy, halogeno (Ci-C ₆ ) alkoxy and

(CVC ₄ ) alkylthio and in the case of cyclic radicals also (dC ₄ ) alkyl and (C ₁ -

C ₄ ) haloalkyl are substituted;

R ₀ ^{4 is} halogen, (C _r C ₄ ) alkyl, (C _r C ₄ ) alkoxy, CF _3; rn _{D is} 1 or 2; v _D is 0, 1, 2 or 3;

such as

Acylsulfamoylbenzoic acid amides, e.g. of the following formula (S-VI), e.g. are known from WO 99/16744,

eg those in which

R ₀ ⁵ = cyclopropyl and (R ₀ ⁴ ) = 2-OMe ("Cyprosulfamide", S3-1),

R ₀ ⁵ = cyclopropyl and (R ₀ ⁴ ) = 5-CI-2-OMe is (S3-2),

R ₀ ⁵ = ethyl and (R ₀ ⁴ ) = 2-OMe is (S3-3), R ₀ ⁵ = iso-propyl and (R ₀ ⁴ ) = 5-CI-2-OMe is (S3-4) and R ₀ ⁵ = iso-propyl and (R ₀ ⁴ ) = 2-OMe (S3-5 );

such as

N-acylsulfamoylphenylurea type compounds of the formula (S-VII), e.g. are known from EP-A-365484,

wherein

R ₀ 8 u _{ι ιn} nd _A DD R 9 are independently hydrogen, (Ci-Cβ) alkyl, (C ₃ -C ₈₎ -cycloalkyl, (C ₃ -C ₆₎ -alkenyl, (C ₃ -C ₆₎ -alkynyl,

R ₀ ^{4 is} halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, CF ₃ m _D 1 or 2;

especially 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea, 1- [4- (N- 4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,

G) Active ingredients from the class of hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives, e.g.

3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 1, 2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001;

H) active compounds from the class of 1, 2-Dihydrochinoxalin-2-ones, for example 1-methyl-3- (2-thienyl) -1, 2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl ) -1,2-dihydroquinoxaline-2-thione, 1- (2-aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one-hydro- Chloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydro-quinoxalin-2-one, as described in WO 2005/12630,

I) active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crop plants such as rice, such as, for example, rice. B.

"Dimepiperate" or "MY-93" (see Pestic. Man.) (= Piperidine-1-thiocarboxylic acid S-1-methyl-1-phenylethyl ester), which is known as a safener for rice against damage by the herbicide Molinate, "daimuron "or" SK 23 "(see Pestic. Man.) (= 1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea), which is known as a safener for rice against damage of the herbicide imazosulfuron,

"Cumyluron" = "JC-940" (= 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254), which is useful as a safener for rice against damage of some Herbicides is known, "methoxyphenone" or "NK 049" (= 3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against damage of some herbicides, "CSB" (= 1-bromo-4 - (chloromethylsulfonyl) benzene) (CAS Reg. No. 54091-06-4 from Kumiai) which is known as safener against damage of some herbicides in rice,

K) Compounds of the formula (S-IX) as described in WO-A-1998/38856

wherein the symbols and indices have the following meanings: R _κ ^1, R _K ² are each independently halo, (Ci -CO-Al kyl, (CrC ₄₎ alkoxy, (Cr _C4) -haloalkyl, (C _{r C4)} - Alkylamino, di- (C 1 -C ₄ ) -alkylamino, nitro; A _κ COORK ³ or COOR _K ⁴ RK ³ . RK ⁴ independently of one another are hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, cyanoalkyl, (C ₁ -C ₄ ) -haloalkyl, phenyl, nitrophenyl, Benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n _κ ¹ 0 or 1 n « ² , n _κ ³ independently of one another 0, 1 or 2

preferably: methyl (diphenylmethoxy) acetate (CAS Regno: 41858-19-9),

L) Compounds of the formula (S-X) as described in WO-A-98/27049

wherein the symbols and indices have the following meanings:

X _L CH or N, nι_ for the case that X = N, an integer from 0 to 4 and for the case that X = CH, an integer from 0 to 5,

RL ^{1 is} halogen, (C _{r C4)} alkyl, (C _{r C4)} -haloalkyl, (C _{r C4)} alkoxy, (C _{r C4)} haloalkoxy,

Nitro, (C _{r C4)} alkylthio, (C _r C ₄₎ alkylsulfonyl, (dC ₄₎ -alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,

R _L ² is hydrogen or (C _r C ₄₎ alkyl, R _L ³ is hydrogen, (Ci-C ₈₎ alkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ alkynyl, or aryl wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of halogen and alkoxy; or their salts.

M) Active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones, for example 1, 2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Regno: 219479-18-2), 1, 2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Regno: 95855-00-8) as described in the WO-A-1999000020 are described, N) Compounds of the formulas (S-XI) or (S-XII) as described in WO-A-2007023719 and WO-A-2007023764

(S-XI) (S-XII) where R _N ^{1 is} halogen, (C _r C ₄ ) alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ Y, Z are each independently O or S, n _{N is} an integer from 0 to 4,

RN ² (CRCI ₆₎ alkyl, _(C2 -Ce) -alkenyl, (C ₃ -C ₆₎ -cycloalkyl, aryl; Benzyl, halobenzyl, R _N ^{3 is} hydrogen, (Ci-C ₆ ) alkyl;

O) one or more compounds from group:

1, 8-naphthalic anhydride,

O, O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfone), 4-chlorophenyl methylcarbamate (mephenate),

O, O-diethyl-O-phenyl phosphorotioate (dietholate),

4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Regno:

31541-57-8)

2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate (MG-838, CAS Regno: 133993-74-5),

Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (from WO-A-

98/13361; CAS Regno: 205121-04-6),

Cyanomethoxyimino (phenyl) acetonitrile (Cyometrinil),

1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinil), 4'-chloro-2,2,2-trifluoroacetophenone-O-1,3-dioxolan-2-ylmethyloxime (Fluxofenim),

4,6-dichloro-2-phenylpyrimidine (fenclorim),

Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

including the stereoisomers and the salts commonly used in agriculture.

A mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.

Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.

The weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.

With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 10000 g / ha or more of active substance, but is preferably between 0.5 and 5000 g / ha, preferably between 0.5 and

1000 g / ha and most preferably between 0.5 and 500 g / ha.

The active compounds of the invention may e.g. used in the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solarium, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledonous cultures of the genera: Arachis, Cucumis, Cucurbita, Daucus, Glycine, Gossypium, Linum, Lycopersicon, Nicotiana, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishumum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

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

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.

The salts according to the invention, in particular the compounds of the formula (I), are also suitable, depending on the concentration, for total weed control, e.g. on industrial and railway tracks and on paths and squares with and without tree cover. Likewise, the active compounds of the present invention may be used for weed control in permanent crops, e.g. Forest, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and

Hop plants, on ornamental and sports turf and grazing areas and for selective weed control in annual crops are used. The salts according to the invention, in particular the compounds of the formula (I), show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence, or in sequential use.

The salts according to the invention, in particular the compounds of the formula (I), show a favorable influence on subsequent cultures (reproduction behavior), i. there was no or extremely low phytotoxicity (such as in the form of (a) light green to yellow leaf veins, (b) yellowing of whole plants, (c) retarded plant growth, (d) abnormal development of younger plant parts or the whole plant) on different subsequent cultures , which are sensitive to the salts according to the invention, in particular the compounds of formula (I), such as sugar beet, sunflower or Cruciferen, such as oilseed rape, mustard and turnip greens observed.

The preparation and the use of the active compounds according to the invention are evident from the examples below.

A. Synthesis Examples

2-lodbenzolsulfonamid

A solution of 10 g (46.88 mmol) of N-tert-butylbenzenesulfonamide in 150 ml of anhydrous tetrahydrofuran is slowly added at -7O ⁰ C with 61.5 ml (98.45 mmol) of a 1.6 molar / i-butyllithium solution in tetrahydrofuran. The solution is briefly warmed to -3O ⁰ C and cooled again to -7O ⁰ C, then 13.9 g are added (51.57 mmol) iodine dissolved in 80 ml of tetrahydrofuran. After the addition, the solution is slowly warmed to room temperature and stirred at this temperature for 3h. Thereafter, it is treated with 50% aqueous sodium thiosulphate Solution and washed with water. The organic phase is dried and evaporated. This gives 4.3 g (27% of theory) of N-tert-butyl-2-iodobenzenesulfonamide. 4.3 g (12.68 mmol) of N-fe / f-butyl-2-iodobenzenesulfonamide are stirred at room temperature in 15 ml of trifluoroacetic acid for 6 h. The solid which results after evaporation of the solution is washed with water. This gives 3.1 g (86% of theory) of 2-iodobenzenesulfonamide.

2-lodbenzolsulfonylisocyanat

To a solution of 5.0 g (17.66 mmol) of 2-iodobenzenesulfonamide in 50 ml of xylene are added 2.1 g (21.2 mmol) of n-butyl isocyanate and 0.04 g (0.35 mmol) of 1, 4-

Added diazabicyclo [2.2.2] octane and stirred for 1 h at 15O ⁰ C (reflux). Thereafter, a solution of 2.27 g (11.48 mmol) of trichloromethyl chloroformate in 10 ml of XyIoI is added dropwise within 1.5 h at 120-125 ⁰ C. The mixture is then stirred at 15O ⁰ C for ¹ h. Finally, the solvent and all volatiles are removed by vacuum distillation. The residue (5.0 g) is used without further purification for further reactions. 2-iodobenzenesulfonyl isocyanate can be detected by IR spectroscopy by the presence of a strong NCO vibrational band at 2238 cm ^-1 . 1 H NMR data: (400 MHz, CDCl ₃ , δ, ppm): 8.19 (dd, J = 1.6 , 7.6, 1 H);

8.17 (dd, J = 1.6, 7.6, 1H); 7.57 (dt, J = 1.6, 8.0, 1 H); 7.33 (dt, J = 2.0, 8.0, 1 H)

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide 250 mg (0.88 mmol) 2-iodobenzenesulfonamide are mixed with 253 mg (0.97 mmol) of (N-phenyloxycarbonyl) amino-4-methoxy-6-methyl-1,3,5-triazine in 3 ml of acetonitrile. Then 0.26 ml (1.77 mmol) of 1,8-diazabicyclo [5.4.0] undec-7-ene are added and the solution is stirred for 1 h at room temperature. The solution is then adjusted slowly to pH 1 with 2N hydrochloric acid. The precipitated solid is filtered off with suction, washed with diisopropyl ether and dried. This gives 360 mg (90% of theory) of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide. 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide sodium salt (= Compound I-2 of the following Table 1) To a solution of 5.0 g (11.13 mmol) of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide in 500 ml of acetonitrile and 50 ml of water are added 0.47 (11.69 mmol) of sodium hydroxide. The solution is stirred at room temperature overnight. After evaporation of the solvents and drying under high vacuum, the sodium salt is obtained in quantitative yield. 1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.97 (br. S, 1 H); 8.03 (dd, J = 1.7, 7.9, 1 H); 7.94 (dd, J = 1.1, 7.8, 1 H); 7.44 (dt, J = 1.2, 7.4, 1 H); 7.10 (dt, J = 1.7, 7.4, 1 H); 3.83 (s, 3H); 2.29 (s, 3H).

In an analogous manner are obtained:

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide potassium salt (= compound I-3 of the following Table 1) by reaction with

Potassium hydroxide.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 9.06 (br. S, 1 H); 8.04 (dd, J = 1.6,

7.9, 1H); 7.94 (dd, J = 1.0, 7.8, 1 H); 7.45 (dt, J = 1.2, 7.7, 1 H); 7.11 (dt, J = 1.5, 7.6,

1H); 3.84 (s, 3H); 2.29 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide

Lithium salt (= compound 1-1 of the following Table 1) by reaction with

Lithium hydroxide.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 9.56 (br. S, 1 H); 8.05 (dd, J = 1.6, 7.9, 1H); 7.95 (dd, J = 1.1, 7.8, 1H); 7.46 (ddd, J = 1.2, 7.4, 7.8, 1 H); 7.11 (dt, J =

1.7, 7.7, 1 H); 3.86 (s, 3H); 2.30 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide magnesium salt (= Compound I-4 of the following Table 1) by reaction with magnesium hydroxide. 1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.96 (br. S, 1 H); 8.05 (dd, J = 1.6, 7.9, 1H); 7.94 (dd, J = 1.1, 7.8, 1 H); 7.44 (dt, J = 1.2, 7.7, 1 H); 7.10 (dt, J = 1.7, 7.5, 1H); 3.84 (s, 3H); 2.30 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide

Calcium salt (= compound I-5 of the following Table 1) by reaction with calcium hydroxide.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.87 (br. S, 1 H); 8.02 (dd, J = 1.7, 7.9, 1H); 7.93 (dd, J = 1.2, 7.8, 1 H); 7.43 (dt, J = 1.2, 7.7, 1 H); 7.08 (dt, J = 1.7, 7.6, 1H); 3.83 (s, 3H); 2.28 (S ₁ 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide (2-hydroxyeth-1-yl) ammonium salt (= Compound 1-19 of Table 1 below ) by reaction with 2-aminoethanol. 1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.03 (dd, J = 1.7, 7.9, 1H); 7.93 (dd, J = 1.2, 7.8, 1H); 7.71 (brs s, 1 H); 7.44 (dt, J = 1.2, 7.8, 1H); 7.09 (dt, J = 1.7, 7.6, 1 H); 5.11 (brs s, 1 H); 3.83 (s, 3H); 3.57 (t, J = 5.3, 2H); 2.85 (t, J = 5.5, 2H); 2.28 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1 ₎ 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide-bis- N, N- (2-hydroxyeth-1-yl) ammonium salt (= compound I -20 of the following Table 1) by reaction with 2,2'-lminodiethanol.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.02 (dd, J = 1.7, 7.9, 1H); 7.93 (dd, J = 1.2, 7.8, 1 H); 7.43 (dt, J = 1.2, 7.7, 1 H); 7.08 (dt, J = 1.7, 7.5, 1H); 5.13 (brs s, 2H); 3.83 (s, 3H); 3.64 (t, J = 5.2, 4H); 2.98 (t, J = 5.5, 4H); 2.28 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide tris-N, N, N- (2-hydroxyeth-1-yl) ammonium salt (= Compound 1-21 of the following Table 1) by reaction with 2,2,2'-nitrilotriethanol: 1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 9.05 (br.s, 1 H); 8.05 (dd, J = 1.4, 7.8, 1H); 7.97 (br d, J = 8.1, 1 H); 7.47 (br t, J = 7.6, 1 H); 7.14 (br t, J = 8.2, 1H); 4.99 (br, s, 3H); 3.86 (s, 3H); 3.65 (br, s, 6H); 3.08 (br, s, 6H); 2.31 (s, 3H). 2-iodo-N - [(4-methoxy-6-methyl-1,3- _l- 5-triazin-2-yl) carbamoyl] benzenesulfonamide ammonium salt (= Compound I-6 of the following Table 1) by reaction with ammonia. 1 H-NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 9.33 (br. S, 1 H); 8.08 (dd, J = 1.6, 7.9, 1H); 8.00 (d, J = 7.6, 1H); 7.50 (t, J = 7.8, 1H); 7.18 (br t, J = 7.3, 1H); 7.12 (brs s, 3H); 3.87 (s, 3H); 2.34 (s, 3H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide isopropylammonium salt (= Compound 1-15 of Table 1 below) by reaction with isopropylamine.

1H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 9.06 (br. S, 1H); 8.04 (dd, J = 1.6, 7.9, 1H); 7.95 (dd, J = 0.9, 7.7, 1H); 7.63 (br s, 3H); 7.46 (dt, J = 1.0, 7.8, 1 H); 7.12 (dt, J = 1.1, 7.4, 1 H); 3.84 (s, 3H); 3.26 (spt, J = 6.6, 1 H); 2.30 (s, 3H); 1.15 (d, J = 6.5, 6H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide tetraethylammonium salt (= Compound 1-12 of Table 1 below) by reaction with tetraethylammonium hydroxide. 1 H-NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.78 (br. S, 1 H); 8.02 (dd, J = 1.6, 7.9, 1H); 7.93 (dd, J = 1.1, 7.8, 1 H); 7.43 (ddd, J = 1.3, 7.4, 7.8, 1H); 7.08 (ddd, J = 1.7, 7.4, 7.7, 1H); 3.82 (s, 3H); 3.19 (m, 8H); 2.27 (s, 3H); 1.15 (m, 12H).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide tetrapropylammonium salt (= Compound 1-14 of Table 1 below) by reaction with tetrapropylammonium hydroxide.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.76 (br. S, 1 H); 8.02 (dd, J = 1.6, 7.9, 1H); 7.92 (dd, J = 1.1, 7.8, 1H); 7.43 (ddd, J = 1.3, 7.4, 7.8, 1 H); 7.08 (ddd, J = 1.7, 7.4, 7.7, 1H); 3.82 (s, 3H); 3.12 (m, 8H); 2.27 (s, 3H); 1.60 (m, 8H); 0.89 (t, J = 7.3, 12H). 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide tetrabutylammonium salt (= Compound 1-18 of Table 1 below) by reaction with tetrabutylammonium hydroxide.

1 H NMR data: (300 MHz, d ₆ -DMSO, δ, ppm): 8.76 (br. S, 1 H); 8.02 (dd, J = 1.7, 7.9, 1H); 7.92 (dd, J = 1.2, 7.8, 1H); 7.42 (dt, J = 1.3, 7.7, 1H); 7.07 (dt, J = 1.7, 7.6, 1 H); 3.82 (s, 3H); 3.16 (m, 8H); 2.26 (s, 3H); 1.57 (m, 8H); 1.31 (m, 8H); 0.93 (t, J = 7.5, 12H).

The compounds described in Table 1 below are obtained as described directly above or analogously to the above examples.

Table 1: Compounds of general formula (I), wherein by M ⁺ the respective salt is designated

B. Formulation Examples

a) A dust is obtained by mixing 10 parts by weight of a salt according to the invention, in particular a compound of formula (I) and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.

b) A wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a salt according to the invention, in particular a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert material,

10 parts by weight of potassium lignosulfonate and 1 part by weight of oleoylmethyltaurine sodium as wetting and dispersing agent and ground in a pin mill.

c) A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a salt according to the invention, in particular a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.

d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

e) A water-dispersible granules are obtained by

75 parts by weight of a compound according to the invention, in particular a compound of the formula (I), 10 parts by weight of calcium lignosulfonate,

5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin mixed, ground on a pin mill and the powder in a fluidized bed through

Spraying of water as granulating liquid granulated.

f) A water-dispersible granules are also obtained by

25 parts by weight of a compound according to the invention, in particular one

Compound of formula (I) ₁

5 parts by wt. 2,2'-dinaphthylmethane-6,6'-disulfonate sodium

2 parts by weight of oleoylmethyltaurine sodium, 1 part by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and

50 parts by weight of water are homogenized on a colloid mill and pre-comminuted, then ground on a bead mill and the resulting suspension is sprayed in a spray tower by means of a single-fluid nozzle and dried.

C. Biological examples

1. weed effect in pre-emergence

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy soil in cardboard pots and covered with soil. The compounds of the invention formulated in the form of wettable powders or emulsion concentrates were then applied to the surface of the cover soil as aqueous suspensions or emulsions having a water application rate of 100 to 800 l / ha in different dosages.

After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the weeds. The optical assessment of the plant or run-on damage was carried out after emergence of the test plants after a test period of 3 to 4 weeks in comparison to untreated Controls. As the results show, compounds of the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.

For example, compounds Nos. 1-1, 1-2, 1-3, 1-4, 1-12, 1-18, 1-19 have

Table 1 very good herbicidal activity against harmful plants such as, Matricaria inodora, Papaver rhoeas, Stellaria media, and Viola tricolor pre-emergence at an application rate of 0.08 kg and less active ingredient per hectare.

2. Post-emergence weed effect - Greenhouse

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the trefoil stage. The compounds of the invention formulated as wettable powders or as emulsion concentrates were sprayed onto the green plant parts in various dosages with an amount of water applied of from 100 to 800 l / ha. After about 10 to 28 days of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations was optically scored compared to untreated controls. The compositions according to the invention also have a good herbicidal activity against a broad spectrum of economically important weed grasses and weeds in postemergence.

For example, compounds Nos. 1-1, 1-2, 1-3, 1-4, 1-12, 1-18, 1-19 of Table 1 have very good herbicidal activity against harmful plants such as Amaranthus retroflexus, Lolium multiflorum, abutilon theophrasti, Matricaria inodora, Ipomoea purpurea, Panicum minor, Stellaria media, Solanum nigrum, Veronica persica and Viola tricolor postemergence at an application rate of 0.08 kg and less active ingredient per hectare. 3. Post-emergence weed action - EXPERIMENTAL DESCRIPTION field

In a direct comparison were under field trial conditions

(Application time 3-5 leaf stage of the tested weeds) the efficacies of the weed control of the known from DE 27 15 786 free acid "2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2 yl) carbamoyl] benzenesulfonamide "with regard to individual salts according to the invention of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide (compound I-3 (potassium salt of 2-iodo-N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and I-4 (magnesium salt of 2-iodo-N - [(4-methoxy) 6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide), the evaluation being carried out 25 days after the application, in terms of efficacy both a representative of a monocot (Panicum minor) and a dicotyledon (Solarium nigrum) weeds are graded according to the following scheme:

0% = no control 100% = full control

Table A-1 below presents the results obtained which clearly demonstrate the weed control improved by the compounds of formula (I) according to the invention, both with respect to monocot and dicotyledon weeds. Table A-1

In a further direct comparison, the efficacies of the weed control of the free acid "2-iodo-N - [(4-methoxy-6-methyl-1), known from DE 27 15 786, were investigated under field test conditions (application time 2-4 leaf stage of the tested weeds). 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide "over the inventive Na ⁺ salt of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide (Compound I-2 according to the invention) at different application rates, the evaluation being carried out 28 days after the application In terms of efficacy, the weeds Chenopodium album, Fagopyron repens and Pennisetum glauca were scored according to the following scheme:

0% = no control 100% = full control

Table A-2 below shows the results obtained which clearly demonstrate the weed control over the free acid improved by compound I-2 according to the invention. Table A-2

4. Crop compatibility

In further experiments in the greenhouse, seeds of a larger number of crops and weeds were laid in sandy loam soil and covered with soil. One part of the pots was treated immediately as described in Section 1, the rest in the greenhouse until the plants have developed two to three true leaves and then sprayed as described in Section 2 with the compounds of the invention in different dosages. Four to five weeks after the application and service life in the greenhouse was determined by optical Bonitur that compounds of the invention graminaceous crops such as barley, oats, rye or wheat in the pre and

Postemergence process was left undamaged even at high doses of active ingredient. Some of the salts according to the invention show high selectivity and are therefore suitable for controlling undesired plant growth in agricultural crops.

5. Reproduction behavior

In further experiments, the test substances were incorporated into the soil in various dosages. Thereafter, various crops were sown in plastic pots with the treated soil and grown in the greenhouse at a day / night rhythm of 22 ° C / 14 ° C. Four weeks later, the rating was as follows.

0% = no damage 100% = complete damage

Tables B1-1 to B1-5 contain the results when sampling sugar beet when using (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates.

Table B1-1

Table B1 -3 Table B1-4

Table B1 -5

Tables B2-1 to B2-5 contain the results of sampling of rape (Brassica napus) in the application of (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates. Table B2-1 Table B2-2 Table B2-3

Table B2-4

Table B2-5

Tables B3-1 to B3-5 contain the results when sampling the field bean (Vicia faba) when using (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates.

Table B3-1

Table B3-2

Table B3-4 Table B3-5

Claims

claims

1. Agrochemically active salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide.

2. Agrochemically active salts according to claim 1 having the general formula (I)

where the cation (M ⁺ )

(a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

(b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or

(d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group Hydroxy (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₆ ) -

Cycloalkyl, (Ci-C ₄₎ alkoxy (Ci-C ₄₎ alkyl, hydroxy (dC ₄₎ alkoxy (CrC ₄₎ alkyl, (CrC ₆₎ -Mercaptoalkyl, phenyl or benzyl groups, where the abovementioned radicals are optionally substituted by one or more identical or different radicals from the group consisting of halogen, such as F, Cl, Br or I, nitro, cyano, azido, (C ₁ -

C ₆ ) alkyl, (C _r C ₆ ) -haloalkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₁ -Ce) -alkoxy, (C ₁ -C ₆ ) -haloalkoxy and phenyl are substituted, and wherein each two If appropriate, substituents on the N atom together form an unsubstituted or substituted ring, or

(e) a phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((CrC ₄ ) alkyl) sulfonium, or (g) an oxonium ion, preferably tri ((C 1 -C ₄ ) alkyl) oxonium, or

(h) is an optionally mono- or polysubstituted and / or by (C-i-C-O-alkyl substituted saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system.

3. Compounds according to claim 2, characterized in that the cation (M ⁺ )

(a) an ion of the alkali metals, preferably lithium, sodium, potassium, or

(b) an ion of the alkaline earth metals, preferably calcium and magnesium, or

(c) an ion of the transition metals, preferably manganese, copper, zinc and iron, or (d) an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group (C _r C ₄ ) alkyl, hydroxy - ^ - OO alkyl, (C ₃ -C ₄ ) cycloalkyl, (dC ₂ ) alkoxy (Ci-C ₂ ) alkyl, hydroxy (C _r C ₂ ) alkoxy - (C 1 -C ₂ ) -alkyl, (C 1 -C ₂ ) -mercaptoalkyl, phenyl or benzyl, where the abovementioned radicals are optionally substituted by one or more identical or different radicals from the group consisting of halogen, such as F, Cl, Br or I, nitro, cyano, azido, (Cr _C2) alkyl, (C _r C ₂₎ -haloalkyl, (C ₃ -C ₄₎ -cycloalkyl, (C _r C ₂₎ alkoxy, (C ₁ - C ₂₎ - Haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N atom together optionally form an unsubstituted or substituted ring, or (E) a quaternary phosphonium ion, preferably tetra - ((CrC ₄ ) alkyl) - phosphonium and tetraphenyl-phosphonium, wherein the (CrC ₄ ) - alkyl radicals and the phenyl radicals optionally mono- or polysubstituted by identical or different radicals from the group halogen such as F, Cl, Br or I ₁ (-C ₂₎ alkyl, (Ci-C ₂₎ -haloalkyl, (C ₃ -

C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) -alkoxy and (C ₁ -C ₂ ) -haloalkoxy are substituted, or

(f) a tertiary sulfonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) sulfonium or triphenyl-sulfonium, where the (C _r C ₄ ) -alkyl radicals and the phenyl radicals are optionally mono- or polysubstituted by identical or different radicals Radicals from the group halogen, such as F, Cl, Br or I ₁ (C _r C ₂ ) -alkyl, (C _r C ₂ ) -haloalkyl, (C ₃ -C ₄ ) -cycloalkyl, (C ₁ -C ₂ ) - Alkoxy and (CrC ₂ ) -haloalkoxy are substituted, or

(g) a tertiary oxonium ion, preferably tri - ((C 1 -C ₄ ) -alkyl) oxonium, where the (C 1 -C ₄ ) -alkyl radicals are optionally mono- or polysubstituted by identical or different radicals from the group consisting of halogen, such as F, Cl, Br or I ₁ (C _r C ₂ ) alkyl, (C _r C ₂ ) haloalkyl, (C ₃ -C ₄ ) cycloalkyl, (CrC ₂ ) alkoxy and (C _r C ₂ ) haloalkoxy are, or (h) a cation from the series of the following heterocyclic

Compounds such as pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, piperidine, pyrrolidine, Morpholine, thiomorpholine, pyrrole, imidazole, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1, 8-

Diazabicyclo [5.4.0] undec-7-ene (DBU).

4. Compounds according to claim 2, characterized in that the cation (M ⁺ ) is a sodium ion, a potassium ion, a lithium ion, a magnesium ion, a calcium ion, a NH ₄ ⁺ ion, a (2-hydroxyeth-1-yl) ammonium ion, bis-N, N- (2-hydroxy) hydroxyeth-1-yl) ammonium, tris-N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methyl ammonium ion, a dimethyl ammonium ion, a trimethyl ammonium ion, a tetramethyl ammonium ion , an ethylammonium ion, a diethylammonium ion, a triethylammonium ion, a tretraethylammonium ion, an isopropylammonium ion

Diisopropylammonium ion, a tetrapropylammonium ion, a tetrabutylammonium ion, a 2- (2-hydroxyeth-1-oxy) eth-1-yl-ammonium-ion, a di- (2-hydroxyeth-1-yl) -ammonium -lon, a trimethylbenzylammonium ion, a tri- ((CrC ₄ ) -alkyl) -sulfonium-ion, or a tri-> CrC ^ -alkyO-oxonium-lon, a benzylammonium ion, a 1-phenylethylammonium-ion, a 2-

Phenylethylammonium ion, a diisopropylethylammonium ion, a pyridinium ion, a piperidinium ion, an imidazolium ion, a morpholinium ion, a 1.δ-diazabicycloIδAOJundec-Z-enium-ion.

5. Compounds according to claim 2, characterized in that the

Cation (M ⁺ ) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, or an NH ₄ ⁺ ion.

6. Compounds according to claim 2, characterized in that the cation (M ⁺ ) is a sodium ion or a potassium ion.

7. Process for the preparation of compounds of claim 2

8. A method for controlling undesired plant growth, characterized in that at least one compound according to one of

Claims 1 to 6 act on unwanted plants and / or their habitat.

9. Use of at least one compound according to any one of claims 1 to 6 for controlling unwanted plants.

10. A herbicidal composition, characterized by a content of a compound according to any one of claims 1 to 6 and conventional extenders and / or surface-active agents.

11. 2-iodobenzenesulfonyl isocyanate of the formula (VI)

12. A process for the preparation of 2-iodobenzenesulfonyl isocyanate, which comprises: iodobenzenesulfonamide of the formula (II)

(H) is reacted with phosgene, diphosgene, or thiophosgene at temperatures between 80 ⁰ C and 150 ⁰ C.

13. A herbicidal agent, characterized by a content of a compound according to any one of claims 1 to 6 and one or more other agrochemical active ingredients.