EP2211621A2 - Use of 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)carbamoyl]benzenesulfonamide and/or salts thereof for combating undesired plant growth in selected useful plant crops or non-cultivated land - Google Patents

Abstract

The invention relates to the use of 2-iodo-N-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)carbamoyl]benzenesulfonamide and/or the salts thereof for selectively combating undesired plant growth (a) in pre-emergence (PE) in cultivated plants, such as wheat (hard and soft wheat), corn, soja, sugar beet, sugar cane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potatoes and millet (sorghum) and (b) in post-emergence (PO) in cultivated plants such as barley, oats, rye, triticale, potatoes, field beans, flax, grazing land and grassed areas/lawns, wherein the above-mentioned cultures, respectively have Summer and Winter varieties and also genetically or mutagenically modified varieties and, (c) in non-cultivated land and cultivated plantations.

Description

 Use of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts for controlling undesired plant growth in selected crops or non-crop land.

description

The invention relates to the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts for the selective control of undesired harmful plants in crops of permanent crops or non-culture crops, or as plant growth regulators alone, or with safeners and / or in combination with other herbicides, the use of which is known to control undesired weeds (such as weeds) in specific crops or as crop protection regulators, with simultaneous and / or sequential application, either as a finished formulation or as a tank mix.

It is known that certain sulfonylureas, such as, for example, chlorosulfuron and metsulfuron-methyl, have herbicidal properties (cf DE 27 15 786). It is furthermore known from WO 2006/114220 that sulphonamides iodinated on the phenyl ring have herbicidal properties. However, the herbicidal action of these known compounds is not in all respects, such as, for example, tolerability, spectrum of activity, rate of action, environmental behavior, soil or non-target plants / secondary cultures (RJ Hance, K. Hoiley, Weed Control Handbook, 8th edition, Blackwell 1990) or application flexibility, satisfactory.

The object of the present invention was improved control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soybeans, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, Barley, oats, rye, triticale, potato and millet (sorghum) and (b) postemergence (PO) in crops such as barley, oats, Rye, tritcale, potato, horse bean, flax, pasture and green / grassy areas, the summer and winter forms and genetically or mutagenically modified varieties being included in the above-mentioned crops, and (c) non-crop land and plantation crops.

Surprisingly, it has been found that this object can be achieved by using the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, optionally in combination with safeners which give adequate compatibility with respect to the crop in question when 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl ) carbamoyl] benzenesulfonamide and / or its salts is not or not sufficiently given.

The present invention thus relates to the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts for the selective control of undesired plant growth (a) pre-emergence (PE) in crops such as wheat (durum wheat and common wheat), maize, soya, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and millet (sorghum ) as well as (b) postemergence (PO) in crops such as barley, oats, rye, triticale, potato, horse bean, flax, pasture and green / grassy areas, of the aforementioned crops respectively summer and winter forms and genetically or mutagenically Varied varieties are included, and (c) in non-crop land and plantation crops.

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide is known, as is its preparation, e.g. from DE 27 15 786 C2, which is hereby incorporated into the present description.

The invention further relates to the use of salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbarnoyl] benzenesulfonamide obtained from 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide obtained by conventional methods. The preparation of such salts is known in the art known, cf. See also European patent application EP 07020807.9 filed on 24.10.2007 by Bayer CropScience AG entitled: "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 "

The preferred subject matter of the present invention is the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the general formula (I)

wherein 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 the same or different

Radicals from the group (C ₁ -C ₄ -alkyl, hydroxy- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl, hydroxy- ( C _r C ₄₎ - alkoxy- (C-ι-C4) alkyl, (C-ι-C ₆₎ -Mercaptoalkyl, phenyl or benzyl substituted, where the radicals mentioned above optionally substituted by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I _{1 is} nitro, cyano, azido, (CrC ₆₎ alkyl, (CrC ₆₎ -haloalkyl, (C ₃ - CβKtycloalkyl, (dC ₆ ) alkoxy, (C _r C ₆ ) 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 phosphonium ion, or

(f) a sulfonium ion, preferably tri ((CrC ₄ ) alkyl) sulfonium, or

(g) an oxonium ion, preferably tri - ((CrC-4) -alkyl) -oxonium, or (h) a saturated or unsaturated / aromatic N, which is optionally singly or multiply fused and / or substituted by (Ci-GjJ-alkyl -containing heterocyclic ionic

Compound is 1-10 carbon atoms in the ring system. for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soybeans, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale , Potato and millet (sorghum) and (b) postemergence (PO) in crops such as barley, oats, rye, tritcale, potato, horse bean, flax, pasture and green / grassy areas, of the above-mentioned crops each summer also winter forms and genetically or mutagenically modified varieties are included, and (c) in non-crop land and plantation crops.

Further preferred is the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of 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 the same or different Radicals from the group (dC ₄₎ -alkyl, hydroxy- (CrC ₄₎ alkyl, (C ₃ - C ₄₎ cycloalkyl, (C _r C ₂₎ alkoxy (CrC ₂₎ alkyl, hydroxy (C _r C ₂ ) - alkoxy- (C _r C ₂ ) alkyl, (CrC ^ mercaptoalkyl, phenyl or benzyl are substituted, wherein the aforementioned radicals optionally by one or more, identical or different radicals from the group halogen, such as F ₁ Cl, Br or I, nitro, cyano, azido, (Ci-C ₂₎ alkyl, (C _r C ₂₎ -haloalkyl, (C ₃ - C ₄₎ cycloalkyl, (C _r C ₂₎ alkoxy, ( CrC 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 - ((C _r C ₄ ) alkyl) phosphonium and tetraphenyl-phosphonium, wherein the (C ₁ -C ₄ ) -alkyl radicals and the phenyl radicals optionally mono- or polysubstituted by the same or various remains from the

Halogen, such as F, Cl, Br or I (-C ₂₎ alkyl, (C ₁ -C ₂₎ - haloalkyl, (C ₃ -C ₄₎ -cycloalkyl, (C _r C ₂₎ alkoxy and (C ₁ -C ₂ ) - substituted haloalkoxy, or

(f) a tertiary sulfonium ion, preferably tri - ((C _{r C4)} alkyl) - sulfonium or triphenyl-sulfonium, wherein the (Ci-C ₄₎ alkyl radicals and the phenyl radicals optionally monosubstituted or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I (-C ₂₎ alkyl, (CrC ₂₎ -haloalkyl, (C ₃ -C ₄₎ - cycloalkyl, (CrC ₂₎ alkoxy and (CrC ₂₎ Haloalkoxy are substituted, or

(g) a tertiary oxonium ion, preferably tri - ((C _{r C4)} alkyl) - oxonium, wherein the (Ci-C ₄₎ -alkyl which is optionally mono- or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I ₁ (C _r C ₂ ) alkyl, (C ₁ -C ₂ ) haloalkyl, (C ₃ -C ₄ ) cycloalkyl, (CrC ₂ ) alkoxy and (C ₁ -C 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, thiomethylhol, pyrrole, imidazole, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1, 8-

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

for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soya,

Sugar beet, cane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and millet (sorghum), and (b) post-emergence (PO) in crops such as barley, oats, rye, triticale, potato, Horse bean, flax, pasture and green / grass areas, the summer and winter forms and genetically or mutagenically modified varieties being included in each of the aforementioned crops, and (c) non-crop land and plantation crops.

Active substances preferably used according to the invention for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soy, sugar beet, sugar cane, rice, cotton, beans, peas, flax, barley, oats , Rye, triticale, potato and millet (sorghum); and (b) post-emergence (PO) in crops such as barley, oats, rye, triticale, potato, horse bean, flax, pasture and green / turf, of the aforementioned crops in summer as well as winter forms and genetically or mutagenically modified varieties are included, and (c) in non-crop land and plantation crops, are the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazine -2-yl) carbamoyl] benzenesulfonamide and the compounds of the formula (I) listed in Table 1 below Table 1: Compounds of general formula (I), wherein by M ⁺ the respective salt is designated

Further preferred is the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the formula (I) in which the cation (M ⁺ ) a sodium ion, a potassium ion, a lithium ion, a magnesium ion, a calcium ion, a NHZ ion, a (2-hydroxyeth-1-yl) ammonium ion, bis- N, N- (2-hydroxyeth-1-yl) ammonium ion, Tris-N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methyl ammonium ion, a dimethyl ammonium ion, a trimethyl ammonium Ion, 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 trimethylbenzyl ammonium ion, a tri (2-hydroxyeth-1-yl) ammonium ion, (C _r C ₄₎ alkyl) -sulfonium- ion, or a tri - ((CrC ₄₎ alkyl) -oxonium ion, a benzylammonium ion, a 1-phenylethylammonium ion, a 2-phenylethylammonium lon, a diisopropylethylammonium ion, a pyridinium ion, a piperidinium ion

Imidazolium ion, a monophosphinium ion, is a 1,8-diazabicyclo [5.4.0] undec-7-enium-ion, for the selective control of undesired plant growth (a) in pre-emergence

(PE) in crops such as wheat (hard and soft wheat), maize, soya, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and millet (sorghum) and (b) post-emergence (PO) in crops such as barley, oats, rye, triticale, potato, horse bean, flax, pasture and green / grassy areas, the summer and winter forms and genetically or mutagenically modified varieties being included in the abovementioned crops, and (c) in non-crop land and plantation crops.

Further preferred is the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the 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, for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as Wheat (durum and common wheat), maize, soya, sugarbeet, sugar cane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and millet (sorghum) and (b) postemergence (PO) in Crops such as barley, oats, rye, tritcale, potato, horse bean, flax, grazing land and green / grassy areas, of the aforementioned crops each including summer and winter forms and genetically or mutagenically modified varieties; and (c) non-crop land and plantation crops.

Particularly preferred is the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the formula (I) in which the cation (M ⁺ ) is a sodium ion, a potassium ion or an NH ₄ -IOn, to selective control of undesired plant growth (a) in pre-emergence (PE) crops such as wheat (hard and soft wheat), corn, soy, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, Potato and millet (sorghum); and (b) post-emergence (PO) in crops such as barley, oats, rye, tritcale, potato, horse bean, flax, pasture and green / grassy areas, of the aforementioned crops each summer, as well Winter forms and genetically or mutagenically modified varieties are included, and (c) in non-crop land and plantation crops.

Very particular preference is given to the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and of compounds of the formula (I) in which Cation (M ⁺ ) is a sodium ion or a potassium ion, for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soybeans, sugar beet, sugarcane, rice , Cotton, beans, peas, flax, barley, oats, rye, triticale, potato and sorghum, and (b) postemergence (PO) in crops such as barley, oats, rye, triticale, potato, horse bean, flax, pasture and green / turf areas, the summer and winter forms and genetically or mutagenically modified varieties being included in each of the aforementioned crops, and (c) non-crop land and plantation crops.

Among the above-mentioned cultivars, the use in the crops of barley, oats, rye is preferred, more preferably in wheat. Barley and oats, and most preferably in wheat and barley.

The abovementioned salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide are obtained in a simple manner by customary salt formation methods, for example by dissolution or dispersion of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide in a suitable diluent, such as methylene chloride, acetone, tert-butyl methyl ether or Toluene, and adding a suitable base. The salts can then - optionally after prolonged stirring - by concentration or suction be isolated. Further and more detailed information on the salt formation of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide can be obtained from the Bayer application filed with the European Patent Office on the same date CropScience AG entitled: "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 ".

In formula (I), 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, enantiomers and diastereomers may 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.

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts, according to the compounds of the formula (I) can be used to control undesirable plant growth. Undesirable plants are understood to mean all plants that grow in places where they are undesirable. These may be, for example, harmful plants (for example weeds or undesired crop plants), for example those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides. 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide The compounds of the formula (I) can be used, for example, against the following plants:

Monocots weeds, e.g. of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ishaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Dicotyledonous weeds, e.g. of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium,

Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia and Fallopia.

On account of their herbicidal and plant growth-regulating properties, the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts are suitable, in particular compounds of the formula (I), also for controlling harmful plants in crops of known or yet to be developed genetically modified plants (hereinafter synonymously called "transgenic plants") (a) pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn , Soybeans, sugar beet, cane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and sorghum, and (b) postemergence (PO) in crops such as barley, oats, Rye, tritcale, potato, horse bean, flax, pasture and green / lawns are used. The transgenic plants are usually characterized by particular advantageous properties, for example, by resistance / tolerance 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 content of 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, the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), can be obtained by virtue of herbicidal and plant growth regulatory properties also for controlling harmful plants in crops of known or yet to be developed by Mutatantenselektion obtained plants (hereinafter synonymously also called "mutagenic plants" or "mutagenic cultures").

Preference is given to the use of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular of compounds of the formula (I) , in economically important transgenic or by mutant selection cultures (a) pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soy, sugar beet, sugarcane, rice, cotton, beans, peas, flax, barley, oats , Rye, triticale, potato and sorghum, and (b) postemergence (PO) in crops such as barley, oats, rye, tritcale, potato, horse bean, flax, pasture and green / grass.

Preferably, the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), as herbicides (a) Pre-emergence (PE) in crops such as wheat (Durum wheat and common wheat), maize, soya, sugarbeet, sugar cane, rice, cotton, beans, peas, flax, barley, oats, rye, triticale, potato and sorghum, and (b) postemergence (PO) in crops such as barley, oats, rye, tritcale, potato, horse bean, flax, grazing land, and green / grassy areas 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 the above-mentioned 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 and varieties which have modified properties in comparison to previously occurring plants consist for example in classical breeding methods - such as hybridization or selection breeding) 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, genetic modifications of crop plants have been described in several cases for the purpose of modifying the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, US Pat.

WO 91/19806), - transgenic crops which are resistant to certain herbicides of the type

Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate

(WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant to produce transgenic crops, for example cotton, with the ability Bacillus thuringiensis toxins (Bt toxins), the plants against make certain pests resistant (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, e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., CoId Spring Harbor Laboratory Press, CoId 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 manipulations, nucleic acid molecules can be used in

Plasmids are introduced which allow mutagenesis or a sequence change 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. It is also possible to use DNA sequences which have a high degree of homology to the coding 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. B. the coding region is linked to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 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, the altered properties by

Overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

Preferably, the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular of compounds of formula (I) in transgenic or cultures obtained by mutant selection or crosses thereof, which eg are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances.

In the application of 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular of compounds of the formula (I) in transgenic or by mutant selection obtained cultures or crosses thereof occur in addition to those observed in other cultures

Effects on harmful plants often have effects specific to the application in the respective transgenic or mutant selection cultures or crosses thereof, for example a modified or specially extended weed spectrum that can be controlled, altered application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, as well as influencing the growth and yield of the transgenic Cultivated plants, as well as the cultivation of these cultures after application of the substances according to the invention.

The invention therefore also relates to the use of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular of compounds of Formula (I), as herbicides to

Control of harmful plants in transgenic and / or by mutant selection of the aforementioned crops or crosses thereof.

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of formula (I), for example, have an excellent Selectivity in barley cultures. They are thus suitable e.g. for the selective control of undesired plant growth, e.g. of harmful plants (for example monocotyledonous and dicotyledonous weeds or undesired crop plants), in barley, for example in the pre-sowing, pre-emergence or postemergence process.

As barley come e.g. transgenic, and non-transgenic, or obtained by mutation selection plants or crosses of the aforementioned plants in question. By way of example, barley varieties such as Beiana, Pasadena, Sebastian and Tocada are mentioned here.

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of the formula (I), can be prepared in customary formulations be converted, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient impregnated natural and synthetic substances, Feinstverkapselungen in polymeric materials. The formulations may contain the usual auxiliaries and additives.

These formulations are prepared in known manner, for example by mixing the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), with extenders, ie liquid solvents, under pressure liquefied gases and / or solid carriers, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents.

In the case of using water as extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. 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 or dimethyl sulfoxide, and water.

Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates; suitable solid carriers for granules are: e.g. crushed 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: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Ligninsulfitablaugen and methylcellulose.

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

The herbicidal action of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular

For example, compounds of formula (I) may be improved equally by surfactants, preferably wetting agents from the range 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 can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, are present, the (eg sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts are used for example as alkali metal salts, such as C ₂ / C ₄ -Fettalkohol- diglycol ether sulfate 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 - 20, preferably 3 - 15 ethylene oxide-containing (C1 ₀ - C-iβ) -, preferably (C10-C ₁ 4) - fatty alcohol polyglycol ethers (for example 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 furthermore comprises the combination of the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula ( l), with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 carbon atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and can be nonionic or ionic (eg as fatty alcohol polyglycol ether sulfates). C ₂ / C ₄ fatty alcohol diglycol ether sulfate sodium (Genapol ^® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3 are preferably - 15

Ethylene oxide units, for example from the Genapol ^® X series, such as Genapol ^® X-030, Genapol ^® X-060, Genapol ^® X-080 and Genapol ^® X-150 (all from Clariant GmbH). Furthermore, it is known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol Polyglykolethersulfate) are also suitable as penetration aids and enhancers for a number of other herbicides (see, for example, EP-A-0502014).

It is further known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g., fatty alcohol polyglycol ether sulfates) are also useful as penetration aids and enhancers for a variety of other herbicides (see, e.g., EP-A-0502014).

The herbicidal action of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), can be reinforced 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 C10-C22, preferably C12-C20

Fatty acids. The Cio-C ₂₂ fatty acid esters are, for example, esters of unsaturated or saturated C ₁₀ -C 20 -fatty acids, in particular having an even number of carbon atoms, eg erucic acid, lauric acid, palmitic acid and especially C-is fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

Examples of do-C ₂₂ fatty acid esters are esters obtained by reacting glycerol or glycol with the CIOC ₂₂ fatty acids obtained as they are, for example, in oils from oil-plant species, or -C ₂ o alkyl CIOC ₂₂ fatty acid esters, such as those by transesterification of the aforementioned glycerol or glycol Cio-C22 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, as described for example in Römpp Chemie Lexikon, 9th edition, volume 2, page 1343, Thieme Verlag Stuttgart.

As a _{Ci-C2o-alkyl-Cio-C 22} fatty acid esters are preferably Methylester, ethyl ester, propyl ester, butyl ester, 2-ethyl-hexyl and dodecyl. Preferred glycol and glycerol-C 20 -C ₂₂ -fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C 1 -C ₂₂ -fatty acids, in particular those fatty acids having an even number of carbon atoms, eg erucic acid, lauric acid, palmitic acid and in particular Cis 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 commercially available in the form of oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ^® (Victorian Chemical Company, Australia, hereinbelow Hasten mentioned, main ingredient: rapeseed oil ethyl ester), Actirob ^® B (Novance, France, hereinafter referred to ActirobB, main component:

Called Rapsölmethylester), Rako-Binol ^® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ^® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ^® (Stefes, Germany, termed Mero called, main component: rapeseed oil methyl ester) may be included.

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, hereinafter referred to as Hasten, main constituent: rapeseed oil ethyl ester), Actirob ^® B (Novance, France, hereinafter referred ActirobB, main ingredient: Rapsölmethylester), Rako-binol ^® (called Bayer AG, Germany, referred to as Rako-binol, main ingredient: rapeseed oil), Renol ^® (Stefes, Germany, termed Renol, vegetable oil ingredient : Rapeseed oil methyl ester) or Stefes ^Mero® (Stefes, Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester). Further, dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

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

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of the formula (I), as such or in their formulations also in mixture with other agrochemical active substances such as known herbicides for controlling unwanted plant growth, eg for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.

As a combination partner for 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of the formula (I), For example, in mixture formulations or in tank mix, for example, known agrochemical active substances can be used, preferably herbicidal active substances which are based on an 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 also in" The Compendium of Pesticide Common Names "available on the Internet as herbicides known from the literature, with 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide or the compounds of the formula (I) can be mentioned, for example, the active compounds from the following list: (Note: The herbicides are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name, if necessary together with a common code number and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers, in particular the commercial form or the commercial forms, unless the context otherwise indicates Salts also include those which are formed by the exchange of a hydrogen atom on the sulfonamide group by a cation, one and in some cases also several A. named forms of application): acetochlor; acibenzolar-S-methyl; acifluorfen (-sodium); aclonifen; AD-67; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] - 2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; Ammoniumpelargonate; AMS, ie ammonium sulfamate; ancimidol; anilofos; asulam; atrazine; aviglycine; azafenidine, azimsulfuron (DPX

A8947); aziprotryn; barban; BAS 516H, ie 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; bilanaphos; 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, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie diethyldithiocarbamic acid 2-chloroallyl ester; 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; diethyl (-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., ethyl ester, 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, eg 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); flurprimidol; 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, i. 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazineamine; MT 5950, i. 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 ester, 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

Although 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of formula (I) already in the The above-mentioned cultures have very good to sufficient selectivity, in principle, in some cultures and especially in the case of mixtures with other herbicides, the less are selective, phytotoxicities occur on crops. In this regard, combinations of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts according to the invention, in particular of compounds of the formula (I) are of particular Interest, which contain these in combination 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. As in economically important crops such as cereals (such as wheat, barley, rye, corn, rice, millet, triticale or oats), sugar beet, sugar cane, oilseed rape, 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: n _A is a natural number from 0 to 5, preferably 0 to 3; RA ¹ is halogen, (C _{r C4)} alkyl, (CrC 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 ),

ITIA is 0 or 1; RA ² is ORA ³ , SR _A ³ or NRA ³ RA 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 bonded to 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 ^, 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, (C _r C ₈ ) alkyl, C ₁ -C 6 haloalkyl), (C ₁ -C ₄ ) alkoxy (C ₁ -C ₈ ) alkyl, cyano or COORA ⁹ , wherein R _A ^{9 is} hydrogen, (C _r C ₈₎ -alkyl, (C _r C ₈₎ haloalkyl, (C _{r C4)} - alkoxy- (C _r C4) alkyl, (Ci-C ₆₎ hydroxyalkyl, _(C3-Ci2) -cycloalkyl or Tn- (C 1 -C ₄ ) -alkyl-silyl;

RA ⁶ , RA ⁷ . RA ⁸ are the same or different hydrogen, (C 1 -C ₈ ) -alkyl,

(CrCβ) -haloalkyl, _(C3-Ci2) -cycloalkyl or substituted or unsubstituted phenyl;

preferably: a) compounds of the type of 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 Fertilize 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 Ethyl 3-carboxylate (S1-3), 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 type of triazole carboxylic acids, preferably compounds such as fenchlorazole (ethyl ester), ie

1- (2,4-Dichloro-phenyl) -5-trichloromethyl- (1 H) -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) Ethyl 2-isoxazoline-3-carboxylate (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds as described in WO 91/08202 or 5,5 -Diphenyl-2-isoxazoline-carboxylic acid ethyl ester (S1-9) ("isoxadifen-ethyl") or n-propyl ester (S1-10) or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3- carboxylic acid ethyl ester (S1-11) as described in the patent application WO-A-95/07897.

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

(S-Il) where the symbols and indices have the following meanings:

RB ^{1 is} halogen, (Ci-C ₄₎ -alkyl, (C _r C ₄₎ -alkoxy, nitro or (dC ^ haloalkyl; n _B is a natural number from 0 to 5, preferably from 0 to 3;

RB ² ORB ³ , SR _B ³ or NR ₆ 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 OR _B ³ , NHR _B 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 Pesticide Mananual.), (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), (5-chloro-8-quinolinoxy) allyl acetate (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-492,366, as well as their hydrates and salts as described in U.S. Pat WO-A-2002/034048. 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) malonic acid, (5-chloro-8-quinolinoxy ) Malonic acid methyl ethyl ester and related compounds, as described in EP-AO 582 198.

C) Compounds of the formula (S-III)

where the symbols and indices have the following meanings: ¹ Rc is (CrC ₄₎ alkyl, (C _{r C4)} -haloalkyl, (C ₂ -C ₄₎ alkenyl, _(C2-C4) haloalkenyl,

(C ₃ -C ₇ ) -cycloalkyl, preferably dichloromethyl;

Rc ² . R c ³ is identical or different hydrogen, (C 1 -C 4) -alkyl, (C 2 -C 4) -alkenyl,

(C ₂ -C ₄₎ -alkynyl, (C _{r C4)} -haloalkyl, (C ₂ -C ₄₎ haloalkenyl, (C _{r C4)} alkylcarbamoyl

(C _{r C4)} alkyl, (C ₂ -C ₄₎ -Alkenylcarbamoyl- (CrC ₄₎ alkyl, (Ci-C ₄₎ alkoxy- (C _{r C4)} alkyl, dioxolanyl (CrC 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 substances of the dichloroacetamide type, often as pre-emergence safeners

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

"Dichloromid" (see Pestic.Man.) (= N, N-diallyl-2,2-dichloroacetamide), "R-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine of the company 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-dioxolan ^ -yO-methyll-dichloroacetamide from PPG Industries),

"DKA-24" (= N-allyl-N-kallylaminocarbonyO-methyll-dichloroacetamide from the company

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 ¹¹ BAS 145138 "or" LAB 145138 "(= 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 R ₀ ⁶ or NHCO-R ₀ ⁷ ;

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

RD ⁶ is hydrogen, (C _r C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl or (C ₂ -C ₆ ) alkynyl, wherein the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy, (C _{r C4)} alkyl, (CrC ₄₎ -alkoxy and (CrC ₄₎ alkylthio, or

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

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

no is 0, 1 or 2; ITID 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 R _D ⁷ (dC ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, wherein the latter two radicals by v _D

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

(CrC ₄ ) alkylthio and in the case of cyclic radicals also (dC ₄ ) alkyl and (Cr

C ₄ ) haloalkyl are substituted;

RD ^{4 is} halogen, (C 1 -C ₄ ) -alkyl, (C 1 -C ₄ ) -alkoxy, CF _3; triD is 1 or 2; v _D is 0, 1, 2 or 3;

such as

Acylsulfamoylbenzoesäureamide, for example, the following formula (S-Vl), for example, are known from WO 99/16744, eg those in which

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

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

RD ⁵ = ethyl and (R ₀ ⁴ ) = 2-OMe is (S3-3),

RD 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 is (S3-5);

such as

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

wherein

R ₀ R ₀ ⁸ and ⁹ are each independently hydrogen, (CrC ₈₎ -alkyl, (C ₃ -C ₈₎ - cycloalkyl, (C ₃ -C ₆₎ -alkenyl, (C ₃ -C ₆₎ -alkynyl, ⁴⁴ RRDD HHaallooggeenn ,, ((CC _r rCC ₄₄ )) - / alkyl, (CrC ₄ ) alkoxy, CF ₃ m _D 1 or 2;

of which in particular 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-methyl-urea,

1- [4- (N-Naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,

G) Active substances from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives, for example ethyl 3,4,5-triacetoxybenzoate, 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 are described;

H) active compounds from the class of 1, 2-dihydroquinoxaline-2-ones, e.g. 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 hydrochloride, 1- (2-methylsulphonylaminoethyl) -3- (2-thienyl) -1,2-dihydrochloride quinoxalin-2-one as described in WO 2005/12630,

I) active substances, in addition to a herbicidal activity against harmful plants also

Safenerwirkung on crop plants such as rice, such as. 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 of the herbicide Molinate,

"Daimuron" or "SK 23" (see Pestic. Man.) (= 1- (1-methyl-1-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron , "Cumyluron" = "JC-940" (= 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254), which is useful as safener for rice against damage some herbicides is known

"Methoxyphenone" or "NK 049" (= 3,3'-dimethyl-4-methoxy-benzophenone) known as safener for rice against damage of some herbicides, "COD" (= 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 H ₂ C ' ^Aκ

wherein the symbols and indices have the following meanings: RK ^1, RK ^2, independently of one another are halogen, (CrC ₄₎ alkyl, (C-ι-C-4) alkoxy, (Cr _C4) -haloalkyl, (C _r C ₄ ) -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 O or m nκ ² , n _κ ^{3 are} independently 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, (dC ₄₎ haloalkoxy,

Nitro, (Ci-C ₄₎ alkylthio, (Ci-C ₄₎ alkylsulfonyl, (C _{r C4)} -alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy, RL ^{2 is} hydrogen or (C 1 -C ₄ ) -alkyl

RL ^{3 is} hydrogen, (C ₁ -Cs) -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 from the group consisting of halogen and alkoxy substituted; or their salts.

M) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones, e.g. 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 WO-A-1999000020,

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 independently of one another O or S, ΠN is an integer from 0 to 4, R _N ² (C _r C ₁₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₃ -C ₆ ) -cycloalkyl, aryl; Benzyl, halobenzyl, R _N ^{3 is} hydrogen, (dC ₆ ) alkyl;

O) one or more compounds from group: 1, 8-naphthalic anhydride,

0.0-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.

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.

As herbicidal combination partners of 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), for an application in barley and other crops are preferably compounds that are selective in barley or other crops, such as amidosulfuron or

Fenoxaprop-ethyl, iodosulfuron, flufenacet, isoproturon, flurtamone, diflufenacet, foramsulfuron, fentrazamide, thiencarbazone-methyl, mesosulfuron (-methyl), pyrasulfotole, isoxaflutole, tembotrione, bispyribac (-sodium), propoxycarbazone (-sdium), or flucarbazone (- sodium).

Also, mixtures of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, in particular compounds of the formula (I), with other known agents such as fungicides, insecticides, acaricides, nematicides, safeners, bird repellants, plant nutrients and soil conditioners are possible.

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of the formula (I), as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is done in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The present invention further relates to a method for controlling undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soy, sugar beet, sugar cane, rice,

Cotton, beans, peas, flax, barley, oats, rye, triticale, potato and sorghum, and (b) postemergence (PO) in crops such as barley, oats, rye, tritcale, potato, horse bean, flax, pasture and Greens / turfs, of the above-mentioned crops in each case summer as well as winter forms and genetically and / or mutagenically modified varieties are included, and (c) in non-crop land and plantation crops, preferably in barley, oats, rye and triticale, one or several compounds of 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and its salts, preferably its salts according to the compounds of formula (I) the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crops), the seed (eg grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (eg the acreage) are applied. They can be applied, for example, before sowing, as well as before and after emergence of the plants. The pre-seed application can be done, for example, by spraying or incorporation into the soil. Also split applications eg in early pre-emergence followed by later postemergence application are possible. Preferred is an application to the accumulated harmful plants, especially before the emergence of barley.

Preferred for selective use in barley, oats, rye and / or triticale, preferably in barley and / or oats, is application to accreted plants, in particular to accrued harmful plants (for example weeds or unwanted crop plants), preferably before the emergence of barley, oats, Rye or / and triticale, more preferably in barley and / or oat, most preferably in barley.

The amount of active ingredient used can vary within a substantial range. It depends essentially on the type of effect desired. In general, the application rates are between 0.01 g and 1000 g of active ingredient per hectare (a.i./ha) of soil surface. In general, lower application rates, e.g. in the range of 0.1 g to 500 g a.i./ha, preferably between 1 g and 150 g a.i./ha, especially in the application to crops, in particular to emerged weeds (e.g., weeds or undesirable crops).

2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts, preferably compounds of the formula (I), have, for example, excellent selectivity in barley, oats, rye and triticale, wherein surprisingly even at low doses of active ingredient, an excellent action against the barley, oats, rye and triticale typically occurring harmful plants is maintained. In particular, occurring in crops of barley, oats, rye and triticale, often difficult to control harmful plants such as species of the genera Centaurea cyanus, Matricaria species, Veronica spec, Viola spec, Poa annua, Agrostis spica -venti, Stellaria media, Papaver spec, Amaranthus spec , Chenopodium spec. and Sinapis arvensis effectively fought. This also applies to species which have a partial or total tolerance or resistance to ALSVACCase inhibitors, in particular structurally related ALS inhibitors. 2-iodo-N - [5-triazin-2-yl) carbamoyl (4-methoxy-6-methyl-1, _3)] benzenesulfonamide, and salts of the invention, especially the compounds of formula (I), in addition show a favorable influence on subsequent cultures, ie no or extremely low phytotoxicity (such as in the form of (a) light green to yellow leaf veins, (b) the yellowing of whole plants, (c) retarded plant growth, (d) abnormal development of recent plant parts or the whole plant) to various subsequent cultures that are sensitive to the salts of 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.

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 damage and / or the emergence damage occurred after emergence of the test plants after a test time 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, 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide as well as the compounds Nos. 1-1, 1-2, 1-3 , 1-4, 1-12, 1-18, 1-19 from Table 1 very good herbicidal activity against harmful plants such as, Lolium multiflorum, Matricaria inodora, Papaver rhoeas, Stellaria media, and viola tricolor in VorauflaufVerfahren at an application rate of 0.1 kg and less active ingredient per hectare.

2. weed effect postemergence

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 3 to 4 weeks 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, 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and the compounds Nos. 1-1, 1-2, 1-3, 1-4, 1-12, I-18 and 1-19 from Table 1 very good herbicidal activity against harmful plants such as Amaranthus retroflexus, Lolium multiflorum, Abutilon theophrasti, Matricaria inodora, Ipomoea purpurea, Stellaria media, Veronica persica and Viola tricolor postemergence at an application rate of 0.1 kg and less active substance per hectare. 3. 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 immediately treated as described in Section 1, the rest in the greenhouse until the plants had developed two to three true leaves and then treated as described in Section 2 with the 2-iodo-N - [(4-methoxy) 6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide, as well as, for example, compounds Nos. 1-1, 1-2, 1-3, 1-4, 1-12, 1-18 and 1-19 from Table 1. Four to five weeks after the application and service life in the greenhouse it was found by optical Bonitur that the tested compounds, barley left either completely undamaged, or left, even at higher application rates only marginal damage traces.

4. 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 in the application of (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates. Table B1-1

Table B1 -4

Tables B2-1 to B2-5 disclose the results of sampling of oilseed rape (Brassica napus) in the application of (a) 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) in the application (a) of the compound I-2 according to the invention and (b) Metsulf uron-methyl at various expense amounts.

Table B3-1

Table B3-3

Claims

claims

1. Use of the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts for the selective

Control of undesirable plant growth for the selective control of undesired plant growth (a) in pre-emergence (PE) in crops such as wheat (hard and soft wheat), corn, soybeans, sugarbeet, sugarcane, rice, cotton, beans, peas, flax, barley, oats , Rye, triticale, potato and millet (Sorghum), and (b) postemergence (PO) in

Crops such as barley, oats, rye, tritcale, potato, horse bean, flax, pasture and green / grassy areas, of the aforementioned crops each including summer and winter forms and genetically or mutagenically modified varieties; and (c) non-crop land and plantation crops.

2. Use according to claim 1, characterized in that it is in the salts of 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide to 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- (C 1 -C ₄ ) -alkyl, ( C ₃ -C ₆₎ -cycloalkyl, (C _{r C4)} alkoxy

(C ₁ -C ₄ ) -alkyl, hydroxy (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₆ ) -mercaptoalkyl, phenyl or benzyl, where the abovementioned radicals are unsubstituted or substituted by one or more, identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido,

-NCO ₁ -NCS ₁ (C _r C ₆ ) -alkyl, (C _r C ₆ ) -haloalkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₁ -Ce) -alkoxy, (C _r C ₆ ) - 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 phosphonium ion, or

(f) a sulfonium ion, preferably tri - ((C -C _{4) alkyl!)} - sulfonium, or

(g) an oxonium ion, preferably tri ((CrC ₄ ) alkyl) oxonium, or

(h) a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 C atoms in the ring system which is optionally singly or multiply fused and / or substituted by (C 1 -C ₄ ) -alkyl.

3. Use according to any one of claims 1 and 2, wherein the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts with an application rate of 0.01 to 1000 g ai / ha be applied.

4. Use according to one or more of claims 1 to 3, wherein the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide or its salts the accumulated harmful plants are applied.

5. A method for the selective control of undesirable plant growth in barley, wherein the 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts as defined in claim 1 or 2, to be applied to the plants, the seed or the surface on which the plants grow.

6. The method according to claim 5, wherein the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its salts at an application rate of 0 , 01 to 1000 g ai / ha are applied.

A method according to claim 5 or 6, wherein the undesired plants are weeds / grass weeds or undesirable crops.

8. The method according to one or more of claims 5 to 7, wherein the 2-iodo-N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) carbamoyl] benzenesulfonamide and / or its Salts are applied to the accumulated harmful plants.