WO2012062749A1 - Benzimidazolidinones that can be used as fungicides - Google Patents

Abstract

The invention relates to novel benzimidazolidinones, to a method for producing same, to the use thereof for combating undesired microorganisms, in particular phytopathogenic fungi, in plant protection, in the domestic and hygiene sectors, and in material protection, and to plant protecting agents containing said benzimidazolidinones.

Description

 BENZIMIDAZOLIDINONE USES AS FUNGICIDES

The present invention relates to novel benzimidazolidinones, processes for their preparation, their use for controlling undesirable microorganisms, in particular phytopathogenic fungi, in crop protection, in the household and hygiene sector and in the protection of materials, and pesticides containing these benzimidazolidinones.

Various benzimidazolidinones are already known as fungicides (cf US 3,249,620). Likewise, various fluorodichloromethylthio compounds and their use in crop protection are known (Angew Chem 1964, 76 (19), 807-816).

Since the ecological and economic demands on modern fungicides are constantly increasing, for example as regards the range of action, toxicity, selectivity, application rate, formation of residues and favorable manufacturability, and also, for example, Problems with resistance can occur, there is the constant task of developing new fungicides that better meet the requirements mentioned at least in some areas.

The present invention now relates to novel benzimidazolidinones of the formulas (I)

in which

R ^{1 is} fluorine or chlorine,

R ^{2 is} hydrogen, C ¹ -C 8 -alkyl or C ³ -C 7 -cycloalkyl,

R ^{3 represents} halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -haloalkoxy,

Ci-C8-haloalkylthio,

n is 0, 1 or 2,

and their agrochemically active salts.

Benzimidazolidinones of the formula (I) according to the invention are very suitable for controlling undesired microorganisms, in particular phytopathogenic fungi. The abovementioned compounds according to the invention can be used both in crop protection, in the area of household and hygiene as well as in the protection of materials.

The benzimidazolidinones of the invention are generally defined by the formula (I). Preferred benzimidazolidinones of the formula (I) are those in which the radicals have the following meanings. These preferred meanings apply equally to the intermediates in the preparation of compounds of formula (I). R ¹ is preferably fluorine.

R ¹ is also preferably chlorine.

R ² is preferably hydrogen, C ¹ -C 6 -alkyl or C ³ -C 6 -cycloalkyl.

R ² particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s- or t-

Butyl or cyclopropyl.

R ² very particularly preferably represents hydrogen, methyl, ethyl or isopropyl.

R ³ is preferably fluorine, chlorine, bromine, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C -haloalkoxy, C 1 -C 6 -haloalkylthio.

R ³ particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trichloromethoxy , Trifluoromethylthio, trichloromethylthio.

R ³ very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trichloromethoxy, trifluoromethylthio, trichloromethylthio. n is preferably 0 or 1.

n is particularly preferably 0.

n is also particularly preferred for 1.

An embodiment of the invention are benzimidazolidinones of the formula (I) in which R ^{1 is} chlorine.

The benzimidazolidinones usable according to the invention may optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.

Benzimidazolidinones can be obtained by known methods (see US 3,249,620). Benzimidazolidinone of the formula (I) is obtained, for example, by

(i) 2-B

in which R ³ and n have the meanings given above,

 first with an alkylating reagent of the formula (III)

I-R ² (III)

in which R ^{2 has} the meanings given above, if appropriate in the presence of a base (for example potassium carbonate) and if appropriate in the presence of a diluent (for example dimethylformamide); and

(11) the formula (IV)

in which R ² , R ³ and n have the meanings given above,

subsequently with halogenated chlorosulfanylmethane derivatives of the formula (V)

in which R ^{1 has} the meanings given above,

 optionally in the presence of a base (e.g., sodium hydride) and optionally in the presence of a diluent (e.g., tetrahydrofuran).

The 2-benzimidazolones required as starting materials for carrying out the process (i) according to the invention are generally described by the formula (II). In this formula, R ³ and n have the preferred, particularly preferred, or most preferred meanings given above. 2-Benzimidazolones of the formula (II) are known. The alkylating reagents which are furthermore required as starting materials for carrying out the process (i) according to the invention are generally described by the formula (III). In this formula, R ^{2 has} the preferred, particularly preferred, or most preferred meanings given above. Alkylating reagents of the formula (III) are known.

The chlorosulphanylmethane derivatives required as starting materials for carrying out the process (ii) according to the invention are generally described by the formula (V). In this formula, R ^{1 has} the preferred meanings given above. Chlorosulfanylmethane derivatives of the formula (V) are known.

The in carrying out the process (ii) further used as starting materials l-alkyl-2-benzimidazolone are generally described by the formula (IV). In this formula, R ² , R ³ and n have the abovementioned preferred, particularly preferred or very particularly preferred meanings. 1-Alkyl-2-benzimidazolones of the formula (IV) are known and can be obtained by process (i). l-Alkyl-2-benzimidazolones of the formula (IV) can also be obtained by (iii) 2-nitro

in which R ³ and n have the meanings given above, first with an alkylating reagent of the formula (III)

I-R ² (III)

in which R ^{2 has} the meanings given above, if appropriate in the presence of a base (for example sodium hydride) and if appropriate in the presence of a diluent (for example tetrahydrofuran); and N-alkyl-2-nitroanilines of the formula (VII) obtained

 in which R, R and n have the abovementioned meanings, hydrogenated under pressure on Pd / C, if appropriate in the presence of a diluent (for example tetrahydrofuran), and the resulting N-alkylbenzene-1,2-diamines of the formula (VIII)

 wherein R, R and n are as defined above, then reacted with methyl chloroformate, optionally in the presence of a base (e.g., sodium hydride) and optionally in the presence of a diluent (e.g., tetrahydrofuran).

The 2-nitroanilines required as starting materials for carrying out the process (iii) according to the invention are generally described by the formula (VI). In this formula, R ³ and n have the preferred, particularly preferred, or most preferred meanings given above.

2-Nitroanilines of the formula (VI) are known.

The present invention further relates to a crop protection agent for controlling undesirable fungi comprising at least one of the benzimidazolidinones of the formula (I). Preferably, they are fungicidal Agents containing agriculturally useful auxiliaries, solvents, carriers, surfactants or extenders.

In addition, the invention relates to a method for controlling unwanted microorganisms, characterized in that according to the invention Benzimidazohdinone of the formula (I) on the phytopathogenic fungi and / or their habitat auszustingt.

According to the invention, the carrier means a natural or synthetic, organic or inorganic substance with which the active ingredients for better applicability, v. A. for application to plants or plant parts or seeds, mixed or combined. The carrier, which may be solid or liquid, is generally inert and should be useful in agriculture. Suitable solid or liquid 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 highly-dispersed silicic acid, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used. Suitable solid carriers for granules are: e.g. Cracked 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 stems.

Suitable liquefied gaseous diluents or carriers are those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halocarbons, as well as butane, propane, nitrogen and carbon dioxide.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may optionally be modified mineral and vegetable oils or waxes. In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane, 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 and dimethyl sulfoxide, and water.

The compositions of the invention may additionally contain other ingredients, such as surfactants. Surface-active substances are emulsifying and / or foam-forming agents, dispersants or wetting agents with ionic or nonionic properties or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, protein hydrolysates, lignin sulphite liquors and methylcellulose. The presence of a surfactant is necessary when one of the active ingredients and / or one of the inert carriers is not soluble in water and when applied in water. The proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.

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. Optionally, other additional components may also be included, e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers, sequestering agents, complexing agents. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

The formulations generally contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% of active ingredient , most preferably between 10 and 70 weight percent.

The active compounds or compositions according to the invention can be used as such or as a function of their physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seeds, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, Foams, pastes, pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, active substance impregnation nated natural and synthetic substances and Feinstverkapselungen in polymeric materials and in coating compositions for seeds, as well as ULV cold and warm mist formulations are used.

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one customary extender, solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, if appropriate Siccative and UV Stabilizers and optionally dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.

The compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.

The active compounds according to the invention, as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) agents such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers , Safeners or semiochemicals. The treatment according to the invention of the plants and plant parts with the active ingredients or agents is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomizing, atomizing, sprinkling, foaming, brushing, spreading, drenching, drip irrigation and propagating material, in particular for seeds by dry pickling, wet pickling, slurry pickling, encrusting, single or multilayer coating, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.

The invention further comprises a method of treating seed.

The invention further relates to seed which has been treated according to one of the methods described in the previous paragraph. The seeds according to the invention are used in methods for protecting seed from undesirable fungi. In these, a seed treated with at least one active ingredient according to the invention is used.

The active compounds or compositions according to the invention are also suitable for the treatment of seed. Much of the damage to crop plants caused by harmful organisms is caused by the seed being dropped during storage or after sowing, as well as during and after germination of the plant. This phase is particularly critical because the roots and shoots of the growing plant are particularly sensitive and may cause only a small damage to the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using suitable means. The control of phytopathogenic fungi by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods of protecting the seed and the germinating plant that provide the additional spreading of plant protection products after sowing or after emergence of plants make redundant or at least significantly reduce. It is also desirable to optimize the amount of active ingredient used so that the seed and the germinating plant are best protected against attack by phytopathogenic fungi, but without damaging the plant itself by the active ingredient used. In particular, methods for treating seed should also include the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of pesticide use.

The present invention therefore also relates to a method of protecting seed and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention. The invention also relates to the use of the seed treatment agents of the invention for protecting the seed and the germinating plant from phytopathogenic fungi. Furthermore, the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.

The control of phytopathogenic fungi which damage plants after emergence is first and foremost due to the treatment of the soil and the aerial plant parts with pesticides. Due to concerns about the potential impact of pesticides on the environment and human and animal health, efforts are being made to reduce the amount of active ingredients applied.

One of the advantages of the present invention is that because of the particular systemic properties of the active compounds or compositions according to the invention, the treatment of the seeds with these active compounds or agents not only the seed itself, but also the resulting plants after emergence before phytopathogenic Protects mushrooms. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.

Likewise, it is to be regarded as advantageous that the active compounds or agents according to the invention can also be used in particular in the case of transgenic seed, wherein the plant growing from this seed is capable of expressing a protein which acts against pests. By treating such seeds with the active compounds or agents according to the invention, it is possible to combat pests already determined by the expression of, for example, insecticidal protein. Surprisingly, a further synergistic effect can be observed, which additionally increases the effectiveness for protection against pest infestation. The compositions according to the invention are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture and viticulture. In particular, these are seeds of cereals (such as wheat, barley, rye, triticale, millet and oats), corn, cotton, soybean, rice, potatoes, sunflower, bean, coffee, turnip (eg sugarbeet and fodder beet), peanut, Rapeseed, poppy, olive, coconut, cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onions and lettuce), turf and ornamental plants (see below). Of particular importance is the treatment of the seeds of cereals (such as wheat, barley, rye, triticale and oats), corn and rice.

As also described below, the treatment of transgenic seed with the active compounds or agents according to the invention is of particular importance. This concerns the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed may e.g. from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Preferably, this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European corn borer and / or Western Com Rootworm. Most preferably, the heterologous gene is from Bacillus thuringiensis.

In the context of the present invention, the agent according to the invention is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a condition that is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used which has been harvested, cleaned and dried to a moisture content of below 15% by weight. Alternatively, seed may also be used which, after drying, e.g. treated with water and then dried again.

In general, care must be taken in the treatment of the seed that the amount of the agent and / or other additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This must be taken into account, above all, with active ingredients which can show phytotoxic effects at certain application rates.

The agents according to the invention can be applied directly, ie without containing further components and without being diluted. In general, it is preferable to apply the agents to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 A, WO 02/080675, WO 02/028186.

The active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.

These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, Wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.

Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.

Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates.

Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably used are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and also tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably used are silicone defoamers, magnesium stearate, silicone emulsions, long-chain alcohols, fatty acids and their salts and also organofluoro compounds and mixtures thereof.

Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.

Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferably, cellulose derivatives, acrylic acid derivatives, polysaccharides, e.g. Xanthan or Veegum, modified clays, phyllosilicates, e.g. Attapulgites and bentonites, and fumed silica.

Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. Gibberellins which may be present in the seed dressing formulations which can be used in accordance with the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmitter", Vol. 2, Springer Verlag, 1970, pp. 401-412). The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds, including seed of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.

For the treatment of seed with the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water, all mixing devices which can usually be used for the dressing can be considered. Specifically, in the pickling procedure, the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed. Optionally, a drying process follows. The active compounds or compositions according to the invention have a strong microbicidal action and can be used to combat undesired microorganisms, e.g. Mushrooms and Bacteria, used in crop protection and material protection.

The benzimidazolidinones according to the invention can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

In crop protection, fungicides for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes can be used.

The fungicidal compositions according to the invention can be used curatively or protectively for controlling phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the active compounds or compositions according to the invention, which are applied to the seed, the plant or plant parts, the fruits or the soil in which the plants grow.

The compositions of the invention for controlling phytopathogenic fungi in crop protection comprise an effective but non-phytotoxic amount of the active compounds according to the invention. "Effective but non-phytotoxic amount" means an amount of the agent of the invention sufficient to control or completely kill the fungal disease of the plant and at the same time not cause any significant symptoms of phytotoxicity size- range vary. It depends on several factors, for example the fungus to be controlled, the plant, the climatic conditions and the ingredients of the compositions according to the invention.

The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offspring and seeds.

The active compounds according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

As plants which can be treated according to the invention, the following main crops are mentioned: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (eg canola), Brassica rapa, B. juncea (eg (field) mustard) and Brassica carinata, rice, Wheat sugar beet, cane, oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables of various botanical taxa such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Tuluaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp. , Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, organs and grapefruit); Solanaceae sp. (for example, tomatoes, potatoes, peppers, eggplants), Liliaceae sp., Compositae sp. (for example, lettuce, artichoke and chicory - including root chicory, endive or common chicory), Umbelliferae sp. (for example, carrots, parsley, celery and celeriac), Cucurbitaceae sp. (for example cucumber - including gherkin, squash, watermelon, gourd and melons), Alliaceae sp. (for example, leek and onion), Cruciferae sp. white cabbage, red cabbage, broccoli, floral cabbage, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage), Leguminosae sp. (for example, peanuts, peas, and beans - such as barley bean and field bean), C enopodiaceae sp. (for example, Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), asparagaceae (for example asparagus); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") Both have been bred by conventional breeding, by magenagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.

The treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially refers to a gene that is provided or assembled outside the plant and that when introduced into the nuclear genome, chloroplast genome or mitochondrial genome imparts new or improved agronomic or other properties to the transformed plant Protein or polypeptide expressed or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference]) , A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location and their growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention can also lead to superadditive ("synergistic") effects. Thus, for example, the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to dryness or water or soil salinity, increased flowering efficiency, harvest relief, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, better shelf life and / or processability of the harvested products.

At certain application rates, the active compound combinations according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi. Plant-strengthening (resistance-inducing) substances in the present context should also mean those substances or substance combinations capable of stimulating the plant defense system in such a way that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi, have a considerable degree of resistance to these undesired ones exhibit phytopathogenic fungi. The substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment. The period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.

Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).

Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

Examples of nematode-resistant plants are e.g. following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 1 1/657,964, 12 / 192,904,111 / 396,808, 12 / 166,253 , 12 / 166,239, 12/166, 124, 12 / 166,209, 1 1 / 762,886, 12 / 364,335, 11 / 763,947, 12 / 252,453, 12 / 209,354, 12 / 491,396 and 12 / 497,221.

Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.

Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved plant growth and plant development, such as water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination power and accelerated maturation. Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and spacing, rooting, Seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in nontoxic compounds, improved processability, and improved shelf life.

Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (e.g., in maize) by delaving (i.e., mechanically removing the male genitalia (s)); however, it is more common for male sterility to be due to genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be achieved by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) which can be treated according to the invention are herbicidally tolerant plants, ie plants that have been made tolerant to one or more given herbicides. Such plants can either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.

Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant of glyphosate using a variety of methods. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpymvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol., 7, 139-145), the genes useful for EPSPS from petunia (Shah et al., 1986, Science 233, 478-481), for an EPSPS from tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704). It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants which select naturally occurring mutations of the above mentioned genes. Plants expressing EPSPS genes conferring glyphosate tolerance are described. Plants which confer other genes which confer glyphosate tolerance, e.g. Decarboxylase genes are described.

Other herbicidally resistant plants are, for example, plants which have been tolerated against herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.

Further herbicide-tolerant plants are also plants which have been made tolerant of the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787. The tolerance of plants to HPPD inhibitors can also be improved by: In addition to a gene coding for an HPPD-tolerant enzyme, plants are transformed with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004/024928. In addition, plants can be made even more tolerant to HPPD inhibitors by incorporating into their genome a gene encoding an enzyme that metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008 / 150473).

Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as acetohydroxy acid synthase, AUAS) confer tolerance to different herbicides or groups of herbicides, e.g. in Tranel and Wright (Weed Science 2002, 50, 700-712). The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described. Other sulfonylurea and imidazolinone tolerant plants are also described.

Other plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf., for example, for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.

The term "insect-resistant transgenic plant" as used herein includes any plant containing at least one transgene comprising a coding sequence encoding: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins by Crickmore et al., (Microbiology and Molecular Biology Reviews 1998, 62, 807-813), updated by Crickmore et al. (2005) on Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac .uk / Home / Neil_Crickmore / Bt /)

or insecticidal parts thereof, e.g. Cry protein class proteins CrylAb, CrylAc, CrylB, CrylC, CrylD, CrylF, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (eg, EP-A 1999141 and WO 2007/107302), or such proteins encoded by synthetic genes as in US Patent Application 12 / 249,016; or

2) a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second crystal protein other than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Nat. Biotechnol. 2001, 19, 668-72; Applied En- vironm. Microbiol. 2006, 71, 1765-1774) or the binary toxin consisting of the CrylA or CrylF proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Application 12 / 214,022 and EP08010791.5); or

 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or

 4) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bbl in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604;

 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VIPs) available at http://www.lifesci.sussex.ac.uk/ Home / Neil_Crickmore / Bt / vip.htm ^ are listed, z. B. Proteins of protein class VIP3Aa; or

 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or

 7) an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or

 8) a protein according to any of items 5) to 7) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102; or

9) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a crystal protein of Bacillus thuringiensis, such as the binary toxin consisting of the proteins VIP3 and CrylA or CrylF (US patent applications 61/126083 and 61/195019), or the binary toxin consisting of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Application 12 / 214,022 and EP 08010791.5); or

10) a protein according to item 9) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or to expand the spectrum of the corresponding target insect species and / or or because of changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein).

Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes coding for the proteins of any of the above-mentioned classes 1 to 10. In one embodiment, an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 10 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor-binding sites in the insect.

An "insect-resistant transgenic plant" as used herein further includes any plant containing at least one transgene comprising a sequence for producing a double-stranded RNA which prevents the growth of that pest after ingestion by an insect pest.

Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:

a. Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.

b. Plants containing a stress tolerance enhancing transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells;

c. Plants containing a stress tolerance enhancing transgene encoding a plant functional enzyme of the nicotm amide dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, have an altered amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product on, such as:

1) Transgenic plants which synthesize a modified starch whose chemical-physical properties, in particular amylose content or amylose / amylopectin ratio, degree of branching, average chain length, side chain distribution, viscosity behavior, gel strength, starch grain size and / or starch grain morphology in comparison with the synthesized starch in wild-type plant cells or plants is altered, so that this modified starch is better suited for certain applications.

 2) Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants that produce polyfructose, especially the inulin and levan type, plants that produce alpha-1,4-glucans, plants that produce alpha-1,6-branched alpha-1,4-glucans, and plants that produce Produce alternan.

 3) Transgenic plants that produce hyaluronan.

 4) Transgenic plants or hybrid plants such as onions with certain properties such as 'high soluble solids content', 'low pungency',

LP) and / or long storage (LS).

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:

a) plants such as cotton plants containing an altered form of cellulose synthase genes,

b) plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants having increased expression of sucrose phosphate synthase; c) plants such as cotton plants with increased expression of sucrose synthase;

d) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. By down-regulating the fiber-selective β-1,3-glucanase; e) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:

a) plants, such as oilseed rape plants, which produce oil of high oleic acid content;

b) plants such as oilseed rape plants, which produce oil with a low linolenic acid content.

c) plants such as rape plants that produce oil with a low saturated fatty acid content.

Plants or plant varieties (which can be obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention are plants such as potatoes, which are virus-resistant, for example against the potato virus Y (Event SY230 and SY233 of Tecnoplant, Argentina), or which are resistant to diseases such as late blight (eg RB gene), or which show reduced cold-induced sweetness (which carry the genes Nt-Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).

Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered seed shattering properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered properties, and include plants such as oilseed rape with delayed or reduced seed failure. Particularly useful transgenic plants which can be treated according to the invention are plants with transformational events or combinations of transformation events which are the subject of issued or pending petitions in the United States Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the non-regulated status. The information is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http: //www.aphis.usda.gov^s/not_reg.html. At the filing date of this application, the APHIS had either given or is pending petitions with the following information:

- Petition: identification number of the petition. The technical description of the transformation event can be found in the individual petition document available from APHIS on the website via the petition number. These descriptions are hereby incorporated by reference. - Enlargement of a petition: reference to a previous petition for which an extension or extension is requested.

 - Institution: name of the person submitting the petition.

 - Regulated article: the affected plant species.

 Transgenic phenotype: the trait conferred on the plant by the transformation event.

 - transformation event or line: the name of the event (sometimes called a line (s)) for which the unregulated status is requested.

- APHIS Documente: various documents that may be published by APHIS regarding the petition or may be obtained from APHIS upon request. Particularly useful transgenic plants which can be treated according to the invention are plants having one or more genes which code for one or more toxins, the transgenic plants sold under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). herbicide-tolerant Plants to be mentioned include corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).

Particularly useful transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities (see, for example, http: // / gmoinfo. jrc. it / gmp _ browse. aspx and http://cera-gmc.org/index.php?evidcode=&hstf^

de = & action = gm_crop_database & mode = Submit).

The active compounds or compositions according to the invention can also be used in the protection of materials for the protection of industrial materials against infestation and destruction by undesired microorganisms, such as e.g. Mushrooms, are used.

Technical materials as used herein mean non-living materials that have been prepared for use in the art. For example, technical materials to be protected from fungal change or destruction by the active compounds of the present invention may be adhesives, glues, paper, wallboard and board, textiles, carpets, leather, wood, paints and plastics, coolants, and other materials infested by microorganisms or can be decomposed. In the context of the materials to be protected, parts of production plants and buildings, e.g. Cooling water circuits, cooling and heating systems and ventilation and air conditioning systems, which may be affected by the proliferation of microorganisms. In the context of the present invention are as technical materials preferably adhesives, glues, papers and cardboard, leather, wood, paints, coolants and heat transfer fluids mentioned, particularly preferably wood. The active compounds or compositions according to the invention can prevent adverse effects such as decay, deterioration, decomposition, discoloration or mold. In addition, the compounds according to the invention can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, wharfage systems and signal systems, which come into contact with seawater or brackish water.

The inventive method for controlling unwanted fungi can also be used for the protection of so-called storage goods. The term "storage goods" is understood to mean natural substances of plant or animal origin or their processed products which have been taken from nature and are desired for long-term protection Storage goods of plant origin, such as plants or plant parts, such as stems, leaves, tubers , Seeds, fruits, grains, can in freshly harvested condition or after processing by (pre-) drying, wetting, crushing, grinding, pressing or roasting. Storage goods also include timber, be it unprocessed, such as timber, power poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin include, for example, skins, leather, furs and hair. The active compounds according to the invention can prevent adverse effects such as modernization, deterioration, decomposition, discoloration or mold.

By way of example, but not by way of limitation, some pathogens of fungal diseases which can be treated according to the invention are named:

Diseases caused by powdery mildews such as e.g. Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotropha species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;

 Diseases caused by causative agents of rust diseases, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phospopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondita or Puccinia triticina; Uromyces species, such as Uro- myces appendiculatus;

 Diseases caused by pathogens of the group of Oomycetes, e.g. Bremia species such as Bremia lactucae; Peronospora species such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species such as Pythium ultimum;

Leaf spot diseases and leaf wilt caused by, for example, Alternaria species such as Alternaria solani; Cercospora species, such as Cercospora beticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium); Colletotrichum species, such as Colletotrichum lindemuthanium; Cycloconium species such as cycloconium oleaginum; Diaphorous species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloósporium species, such as, for example, Gloeosporium laeticolor; Glomerella species, such as, for example, Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Microdochium species such as Microdochium nivale; Mycosphaerella species, such as Mycosphaerella graminicola and M. fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as, for example, Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species such as Venturia inaequalis; Root and stem diseases caused by, for example, corticium species, such as, for example, Corticium granearum; Fusarium species such as Fusarium oxysporum; Gaeumannomyces species such as Gaeumannomyces graminis; Rhizoctonia species, such as Rhizoctonia solani; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola;

Ear and panicle diseases (including corncob) caused by e.g. Alternaria species, such as Alternaria spp .; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species such as Monographella nivalis; Septoria species, such as Septoria nodorum;

 Diseases caused by fire fungi, e.g. Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species such as Tilletia caries, T. controversa; Urocystis species, such as Urocystis occulta; Ustilago species such as Ustilago nuda, U. nuda tritici; Fruit rot caused by e.g. Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species such as Penicillium expansum and P. purpurogenum; Sclerotinia species, such as Sclerotinia sclerotiorum;

Verticilium species such as Verticilium alboatrum;

 Seed and soil rots and wilts, as well as seedling diseases caused by e.g. Fusarium species such as Fusarium culmorum; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;

Cancers, galls and witches brooms caused by e.g. Nectria species, such as Nectria galligena;

 Wilt diseases caused by e.g. Monilinia species such as Monilinia laxa;

Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, such as Taphrina deformans;

 Degenerative diseases of woody plants caused by e.g. Esca species such as Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;

Flower and seed diseases caused by e.g. Botrytis species, such as Botrytis cinerea;

 Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani;

Diseases caused by bacterial agents such as e.g. Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora.

Preferably, the following diseases of soybean beans can be controlled: Fungus diseases on leaves, stems, pods and seeds caused by, for example, Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Dandelion leaf leaf (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii) Phyllostica Leaf Spot (Phylosticta sojaecola), Pod and Stem Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi, Phakopsora meibomiae), Scab (Sphaceloma glycines), Leaf Blight Stemphyli (Stemphylium botryosum), Target Spot (Corynespora cassiicola) ,

 Fungal diseases on roots and stem base caused by e.g. Black Root Red (Calonectria cro- talariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wilt, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semi- titectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris ), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium red (Pythium aphanidermatum, Pythium irregular, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).

As organisms that can cause degradation or alteration of the technical materials, mushrooms are called. The active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes). Examples are fungi of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, like Chaetomium globosum; Coniophora, like Coniophora puetana; Lentinus, like Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophomapityophila; Trichoderma, like Trichoderma viride.

In addition, the active compounds according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character. When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the mode of administration. The application rate of the active compounds according to the invention in the treatment of plant parts, eg leaves: from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, particularly preferably from 50 to 300g / ha (when used by casting or Drops can even reduce the rate of application, especially if inert substrates such as rockwool or perlite are used);

in seed treatment: from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12.5 g per 100 kg of seed;

in the case of soil treatment: from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.

These application rates are given by way of example only and not by way of limitation within the meaning of the invention.

The active compounds or compositions according to the invention can therefore be used to protect plants within a certain period of time after the treatment against attack by the mentioned pathogens. The period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active ingredients or up to 200 days after seed treatment.

In addition, can be reduced by the treatment according to the invention, the mycotoxin content in the crop and the food and feed produced therefrom. Specifically, but not exclusively, mycotoxins include: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxin, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxyscirpenol (DAS) , Beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which may be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acuminatum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum ( Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. slowethiae, F. subglutinans, F. tricinctum, F. verticillioides, and others as well as of Aspergillus spec., Penicillium spec., Claviceps purpurea, Stachybotrys spec. et al

The listed plants can be treated particularly advantageously according to the invention with the benzimidazolidinones of the formula (I) or the agents according to the invention. The preferred ranges given above for the active compounds or agents also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or agents specifically mentioned in the present text. Preparation Examples

 Preparation of 1 - {(dichloro (fluoro) methyl-1-sulfanyl} -3-tetrahydro-1,3-dihydro-2H-benzimidazol-2-one

 (Example No. 7)

 A solution consisting of 22.4 g (90.0 mmol) of 1-ethyl-1,3-dihydro-2H-benzimidazol-2-one in 250 ml of tetrahydronfuran was added carefully under argon with 4.68 g (117.0 mmol). Sodium hydride (60%) added. Then 19.8 g (117.0 mmol) of dichloro (chlorosulfanyl) fluoromethane was added dropwise and stirred at 80 ° C for 20 hours. After cooling to room temperature, water was added cautiously. The product was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography (mobile phase cyclohexane, methylene chloride gradient). This gave 25 g (92%) of 1 - {[dichloro (fluoro) methyl] sulfanyl} -3-ethyl-1,3-dihydro-2H-benzimidazol-2-one with a content of 98% according to LC-MS and a logP (sour) of 3.24.

 Ή-NMR (400MHz, DMSO-d) δ ppm: 1, 20-l, 30 (m, 1H); 3.90-4.00 (m, 1H); 7.10-7.40 (m, 1H).

Preparation of starting materials of the formula (IV)

 Preparation of 1-ethyl-1,3-dihydro-2H-benzimidazol-2-one (IV-1)

 A solution consisting of 0.68 g (5.0 mmol) of N-ethylbenzene-l, 2-diamine in 30 ml of toluene was added carefully under argon with 0.30 g (7.5 mmol) of 60% sodium hydride and at room temperature Stirred for 30 minutes. Subsequently, 0.57 g (6.0 mmol) of methyl chloroformate was added and stirred at room temperature for 1 hour and at 140 ° C for 5 hours. After cooling to room temperature, water was added cautiously. The product was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated in vacuo. This gave 0.90 g (91%) of 1-ethyl-1,3-dihydro-2H-benzimidazol-2-one with a content of 82% according to LC-MS and a logP (acid) of 1.28. Preparation of starting materials of the formula (VIII)

Preparation of ethylbenzene-1,2-diamine (VIII-1)

(VIII-1)

A solution consisting of 4.51 g (25 mmol) of N-ethyl-2-nitroaniline in 22 ml of tetrahydrofuran was mixed with 0.3 g of Pd / C (5%) and then hydrogenated at room temperature for 4 hours with 10 bar of hydrogen. Subsequently, the catalyst was filtered off and the product concentrated in vacuo. This gave 3.80 g (> 95%) of N-ethylbenzene-l, 2-diamine with a content of 98% according to GC MS.

Preparation of starting materials of the formula (VIII)

Preparation of ethyl 2-nitroaniline (VII-1)

 A solution consisting of 1.38 g (10.0 mmol) of 2-nitroaniline in 50 ml of tetrahydrofuran was added carefully under argon with 0.479 g (12.0 mmol) of sodium hydride (60%) and stirred at room temperature for 1 hour. Subsequently, 2.31 g (15.0 mmol) of dimethyl sulfate was added and stirred at 80 ° C for 2 hours. After cooling to room temperature, water was added cautiously. The product was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated in vacuo. There was obtained 1.85 g (95%) of N-ethyl-2-nitroaniline with a content of 85% by LC-MS and a logP (acid) of 2.68. According to the general descriptions of the processes according to the invention, the compounds of the formula (I) mentioned in the following table can be obtained.

Table 1

Me = methyl, Et = ethyl, iPr = i-propyl The determination of the logP values given in the preceding Tables and Preparation Examples is carried out according to EEC Directive 79/831 Annex V. A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

 The determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile

 The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).

The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

applications

 Example A: Alternaria - Test (Tomato) / Protective

Solvent: 24.5 parts by weight of acetone

 24.5 parts by weight of dimethylacetamide

 Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

 To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation booth at about 20 ° C and 100% relative humidity. 3 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.

Example B: Blumeria graminis test (barley) / protective

Solvent: 49 parts by weight of N, N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

 To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, the plants are planted with spores of Blumeria graminis f.sp. ordei dusted. The plants are placed in a greenhouse at a temperature of about 18 ° C and a relative humidity of about 80% to promote the development of mildew pustules. 7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficacy of 70% or more at an active ingredient concentration of 1000 ppm.

Example C: Phytophthora test (tomato) / protective

Solvent: 24.5 parts by weight of acetone

 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

 To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation booth at about 20 ° C and 100% relative humidity. 3 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.

Connection No. Efficiency (%)

 1 95

 2 81

 3 78

4 91

Example D: Plasmopara test (vine) / protective

Solvent: 24.5 parts by weight of acetone

 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

 To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then left for 1 day in an incubation booth at about 20 ° C. and 100% relative atmospheric humidity. Subsequently, the plants are placed in the greenhouse for 4 days at about 21 ° C and about 90% humidity. The plants are then moistened and placed in an incubation booth for 1 day. 6 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.

Example E: Septoria tritici test (wheat) / protective

Solvent: 49 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours at 20 ° C and 100% relative humidity in an incubation cabin. Thereafter, the plants are placed under a transparent hood at 15 ° C and 100% relative humidity for another 60 hours. The plants are grown in a greenhouse at a temperature of about 15 ° C and a relative humidity of 80%. 21 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficacy of 70% or more at an active ingredient concentration of 1000 ppm.

Example F: Venturia test (apple) / protective

Solvent: 24.5 parts by weight of acetone

 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

 To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequales and then remain in an incubation cabin for 1 day at about 20 ° C. and 100% relative atmospheric humidity. The plants are then placed in the greenhouse at about 21 ° C and a relative humidity of about 90%. 10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed. In this test, the following compounds according to the invention show an efficiency of 70% or more at a concentration of active ingredient of 100 ppm.

Connection No. Efficiency (%)

 1 99

 2 89

 4 93

 5 99

 6 100

 7 100

Claims

claims

Benzimidazolidinones of the formula (I)

 in which

R ^{1 is} fluorine or chlorine,

R ^{2 is} hydrogen, C ¹ -C 8 -alkyl or C ³ -C 7 -cycloalkyl,

R ^{3 represents} halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -synyl

Haloalkoxy, Ci-Cs-haloalkylthio,

 n is 0, 1 or 2,

 and their agrochemically active salts.

2. Benzimidazolidinone of the formula (I) according to claim 1, in which R ^{1 is} chlorine.

3. A composition for controlling unwanted microorganisms, characterized by a content of at least one of the benzimidazolidinones of the formula (I) according to claim 1 in addition to extenders and / or surface-active substances.

4. Use of Benzimidazolidinonen of the formula (I) according to claim 1 for controlling unwanted microorganisms.

5. Use of Benzimidazolidinonen of the formula (I) according to claim 1 for controlling phy- topathogenic fungi in crop protection and material protection.

6. A method for controlling unwanted microorganisms, characterized in that benzimidazolidinones of the formula (I) according to claim 1 to the microorganisms and / or their

Habitat.

7. A process for preparing means for controlling unwanted microorganisms, characterized in that mixing Benzimidazolidinone of the formula (I) according to claim 1 with extenders and / or surface-active substances.

8. Use of Benzimidazolidinone of the formula (I) according to claim 1 for the treatment of transgenic plants.

9. A process for the preparation of Benzimidazolidinonen of the formula (I) according to claim 1, characterized in that (ii) -alkyl-2-benzimidazolones of the formula (IV)

 in which

R ^{2 is} hydrogen, C ¹ -C 8 -alkyl or C ³ -C 7 -cycloalkyl,

R ^{3 is} halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio

Cs-haloalkoxy, Ci-Cs-haloalkylthio,

 n is 0, 1 or 2,

an-derivatives of the formula (V)

 in which

R ^{1 is} fluorine or chlorine,

 optionally in the presence of a base (e.g., sodium hydride) and optionally in the presence of a diluent (e.g., tetrahydrofuran).

Process for the preparation of benzimidazolidinones of the formula (I) according to Claim 1, characterized in that

either

(i) 2-benzimidazolones of the formula (II)

 in which

R ^{3 represents} halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 8 -alkylthio,

Cs-haloalkoxy, Ci-Cs-haloalkylthio,

 n is 0, 1 or 2,

 first with an alkylating reagent of the formula (III)

I-R ² (III)

 in which

R ^{2 is} hydrogen, C ¹ -C 8 -alkyl or C ³ -C 7 -cycloalkyl,

 optionally in the presence of a base (e.g., potassium carbonate) and optionally in

The presence of a diluent (e.g., dimethylformamide) is reacted;

or

(iii) 2-nitroanilines of the formula (VI)

in which R ³ and n have the meanings given above,

first with an alkylating reagent of the formula (III)

I-R ² (III)

in which R ^{2 has} the meanings given above,

optionally in the presence of a base (e.g., sodium hydride) and optionally in the presence of a diluent (e.g., tetrahydrofuran); and

the thus-obtained N-alkyl-2-nitroanilines of the formula (VII)

in which R ² , R ³ and n have the meanings given above,

optionally hydrogenated under pressure of Pd / C in the presence of a diluent (e.g., tetrahydrofuran) and the resulting N-alkylbenzene-1,2-diamines of the formula

(VIII)

in which R ² , R ³ and n have the meanings given above,

subsequently with methyl chloroformate, if appropriate in the presence of a base (for example sodium hydride) and if appropriate in the presence of a diluent (for example tetrahydrofuran); olone of the formula (IV)

in which R ² , R ³ and n have the meanings given above,

an-derivatives of the formula (V)

is fluorine or chlorine, if appropriate in the presence of a base (for example sodium hydride) and if appropriate in the presence of a diluent (for example tetrahydrofuran).