WO2014095704A1

WO2014095704A1 - Herbicidal agents containing aclonifen

Info

Publication number: WO2014095704A1
Application number: PCT/EP2013/076676
Authority: WO
Inventors: Dominique Schreiber; Thomas Wilde; Dirk BRÜGGEMANN
Original assignee: Bayer Cropscience Ag
Priority date: 2012-12-18
Filing date: 2013-12-16
Publication date: 2014-06-26
Also published as: AR093998A1

Abstract

The invention relates to herbicidal agents having an effective amount of aclonifen and the additional herbicides chlorotoluron and diflufenican. These herbicidal agents have an improved range of application.

Description

Description Herbicidal agents containing aclonifen

The invention is in the technical field of pesticides which are useful against harmful plants e.g. can be used in crops and contain as active ingredients in the herbicidal compositions a combination of aclonifen and another herbicide.

The herbicidal active ingredient Aclonifen (manufacturer: Bayer CropScience) belongs to the group of diphenyl ethers and mixtures of this group with other herbicides are known from the literature: for example (for example) US Pat. No. 4,394,159 A, EP 0007482 A. In US Pat. No. 5,858,920 B, inter alia heteroaryloxy-acetamides are mixed With

Single agents, e.g. the herbicide Aclonifen, but without experimental data for the synergistic effect.

The herbicidal active ingredient Aclonifen is characterized by a broad activity against monocotyledonous and dicotyledonous harmful plants and is obtained e.g. predominantly pre-emergence in sown and / or planted agricultural or horticultural crops, as well as on non-crop areas (e.g., in crops such as

Wheat, barley, rye, oats, triticale, rice, maize, millet, sugar beet, sugarcane, rapeseed, cotton, sunflower, soya, potato, tomatoes, beans, flax, pasture, fruit orchards, plantation crops, lawns and lawns, as well as residential squares - and industrial plants, railway tracks).

Aclonifen is commercially available as a single active ingredient, for example under the trade names Challenge®, Bandur®, Fenix® and Prodigio®. In addition to using the

Single active substances are also mixtures of aclonifen with other herbicides known from the literature (eg AU 635599 B, AU 642986 B, AU 641500 B, AU 659028 B, AU 663028 B, AU 712501 B, US 6046133 B, EP 0958742 A) and commercially: Mixture with Amitrole (eg Derby®, lllico TL Express®, Muleta®), with isoxaflutole (eg

Acajou®, Lagon®, Merlin Combi®), with Alachlor (eg Manager®), with Flurtamone (eg Nikeyl®), with oxadiargyl (eg Opalo®, Carioca®) and with oxadiazon (eg Phare®, Cline®).

Despite the good effect of Aclonifen as a single active ingredient and in the already known mixtures there is still a need to improve the application profile of this drug in specific applications. The reasons for this are manifold, such as further increase the effectiveness in special applications and with different soil properties as well

Irrigation conditions, increase crop compatibility, response to new production techniques in individual crops and / or on the increasing occurrence of herbicide-resistant harmful plants (eg in cereals, rice and corn but also in potatoes, sunflowers, peas, carrots and fennel) with, for example, 'target -Site Resistance '(eg TSR (abbreviation: TSR, where the weed populations contain biotypes with a site-specific resistance, ie by natural mutations in the gene sequence changes the binding site at the site of action, so that the drugs no longer or insufficiently bind and can act accordingly) and 'Enhanced Metabolism Resistance' (abbreviation: EMR), where the weed populations contain biotypes with metabolic resistance, ie the plants have the ability via enzyme complexes

The active ingredients are metabolized faster in the plant. According to the 'Herbicide Resistance Action Committee'

(Abbreviation: HRAC, a working group of the research industry)

Resistances for approved drugs classified according to their mode of action (MoA): e.g. HRAC group A = acetyl coenzyme A carboxylase inhibitors (MoA: ACCase) or HRAC group B = acetolactate synthase inhibitors (MoA: ALS). These enhancements to the application profile can be significant both individually and in combination.

One way to improve the application profile of a herbicide may be to combine the active ingredient with one or more other suitable ones

Active ingredients exist. However, phenomena of chemical, physical and chemical phenomena often occur in the combined use of several active substances

biological incompatibility, eg lack of stability in a coformulation, Decomposition of an active substance or antagonism of the active ingredients. Desired, however, are combinations of active ingredients with favorable effect profile, high stability and synergistically enhanced as possible effect, which allows a reduction in the application rate compared to the single application of the active ingredients to be combined. Also desirable are combinations of active ingredients that generally increase crop plant tolerance and / or specific ones

Production techniques can be used. This includes, for example, a reduction in the sowing depth, which can often not be used for reasons of cultural compatibility. This generally achieves a faster casserole of the crop, reduces its risk of casserole diseases (such as Pythium and Rhizoctonia), improves overwintering ability and the degree of tillering. This also applies to late-seed, which would otherwise not be possible due to the risk of cultural compatibility. The object of the present invention was to improve the

Application profile of the herbicidal active ingredient Aclonifen with regard to:

a simplified application method, which reduces the costs for the

Reduce users and thus be more gentle on the environment impact;

- an improvement and application flexibility of the effect safety

Soils with different soil properties (e.g.

Moisture);

- an improvement and application flexibility of the effect safety under different irrigation conditions;

an improvement in the application flexibility of the active substances from preemergence to postemergence of the cultivated and weed plants, in particular monocotyledonous weed plants;

- an improvement of the efficacy of resistant weed species, which would allow a new possibility for an effective resistance management;

where the last two tasks were in the foreground. This object has been achieved by providing herbicidal compositions comprising aclonifen and the other herbicides chlorotoluron and diflufenican.

An object of the invention are thus herbicidal compositions containing as the only herbicidally active ingredients:

A) Aclonifen (component A),

B) chlorotoluron (component B) and

C) diflufenican (component C). The active ingredients mentioned in this description with their "common name"

(herbicidally active ingredients) are, for example, from "The Pesticide Manual", 15th Edition 2009, or in the corresponding "The e-Pesticide Manual", Version 5.2 (2008-2011), each issued by the BCPC (British Crop Protection Council) , and from "The Compendium of Pesticide Common Names" on the Internet (website: http://www.alanwood.net/pesticides/) known.

The herbicidally active ingredients component A, B and C are hereinafter referred to collectively as "(single) agents", "(single) herbicides" or as "herbicidal components" and are used as individual substances or as a mixture e.g. known from "The Pesticide Manual", 15th edition (s.o.) and have the following

Registration numbers (abbreviation: "PM # .." with the current one

Entry number / "sequential entry number"):

Component A: Aclonifen (PM # 10), e.g. 2-chloro-6-nitro-3-phenoxybenzeneamines;

Component B: chlorotoluron (PM # 154), e.g. A / '- (3-chloro-4-methylphenyl) - Λ /, / V-dimethylurea;

Component C: diflufenican (PM # 271), e.g. A / - (2,4-difluorophenyl) -2- [3- (trifluoromethyl) phenoxy] -3-pyridinecarboxamide.

If the short form of the "common name" of an active substance is used in the context of this description, then - if applicable - are in each case all common derivatives, such as the esters and salts, and isomers, in particular optical isomers includes, in particular the commercial form or forms. Will with the

"Common name" denotes an ester or salt, so are all other common derivatives such as other esters and salts, the free acids and neutral compounds, and isomers, in particular optical isomers, in particular the commercial form or forms. The chemical link names given refer to at least one of the "common name" compounds, often a preferred compound.

As far as the abbreviation "AS / ha" is used in this description, this means "active substance per hectare", based on 100% active ingredient. All percentages in the description are percentages by weight (abbreviation: "% by weight") and, unless otherwise defined, relate to the relative weight of the respective ones

Component based on the total weight of the herbicidal agent (e.g., as a formulation).

The herbicidal compositions according to the invention have a herbicidally active content of the components A, B and C and may contain further constituents, e.g. agrochemical active substances from the group of insecticides, fungicides and safeners and / or additives customary in crop protection and / or

Formulation aids, or used together with these.

In a preferred embodiment, the herbicidal compositions according to the invention have synergistic effects as an improvement of the application profile. These synergistic effects can e.g. co-application of the herbicidal components, but they can often be detected even in case of splitting. It is also possible

Application of the individual herbicides or herbicide combinations in multiple portions (sequence application), eg pre-emergence applications, followed by postemergence applications or early postemergence applications, followed by mid-late post-emergence applications. Preference is given to the joint or the timely application of the active ingredients of the herbicidal compositions of the invention. The synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency at the same rate, the control of previously unrecognized species (gaps), an extension of the

Period of application and / or a reduction in the number of necessary

Individual applications and - as a result for the user - economically and ecologically more advantageous weed control systems.

The application rate of the herbicidal components and their derivatives in the herbicidal composition can vary within wide limits. In applications with application rates of 261-9500 g AS / ha of the herbicide components is in the pre and

Postemergence control a relatively wide range of annual and perennial weeds, grass weeds and Cyperaceae.

The application rates of the herbicidal components are in the herbicidal composition in the following weight ratio to each other:

(Range component A): (range component B): (range component C) in general (1-100) :( 1-100) :( 0.1-100)

preferably (1-25) :( 1-25) :( 0.5-50),

particularly preferred (1-10) :( 1-10) :( 1-10).

The application rates of the respective herbicidal components in the herbicidal composition are:

Component A: generally 10 to 5000 g AS / ha, preferably 80 to 3000 g AS / ha, more preferably 80 to 1000 g AS / ha aclonifen;

Component B: generally 250-4000 g AS / ha, preferably 350-1800 g AS / ha, more preferably 350-1500 g AS / ha chlorotoluron;

Component C: generally 1 to 500 g AS / ha, preferably 10 to 300 g

AS / ha, more preferably 30-200 g AS / ha diflufenican.

Accordingly, from the above-mentioned application rates

Percent by weight (% by weight) of the herbicidal components based on the

Total weight of herbicidal agents are calculated, which may additionally contain other ingredients. The herbicidal compositions according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants such as weeds, grass weeds or cyperaceans, including species which are resistant to herbicidal active compounds such as glyphosates, glufosinates, atrazine, photosynthesis inhibitors, imidazolinone herbicides , Sulfonylureas, (hetero) aryloxy-aryloxyalkylcarboxylic acids or -phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedione oximes (so-called 'dims') or auxin inhibitors. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients. The substances can be applied, for example, in pre-sowing, pre-emergence or post-emergence processes, for example jointly or separately.

In particular, some representatives of mono- and dicots are

Called weed flora, which can be controlled by the herbicidal compositions according to the invention, without being limited by naming a restriction to certain species.

On the side of the monocotyledonous weeds, e.g. Avena spp., Alopecurus spp., Apera spp., Brachiaria spp., Bromus spp., Digitaria spp., Lolium spp.,

Echinochloa spp., Leptochloa spp., Fimbristylis spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and Cyperus species from the annuelle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusarten well. For dicotyledonous weed species, the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp. , Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. Eclipta spp., Sesbania spp., Aeschynomene spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds. When the herbicidal compositions according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die completely after two to four weeks have elapsed.

When applying the herbicidal compositions of the invention to the green

Plant parts postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the stage of growth existing at the time of application or die after a certain time completely off, so that eliminated in this way harmful to crops weed competition very early and sustainable becomes. The

herbicidal compositions according to the invention can also be applied in rice in the water and are then taken up via soil, shoot and root.

The herbicidal compositions according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action. The rainfastness of the active ingredients in the compositions according to the invention is generally favorable. A particular advantage is the fact that the effective and used in the compositions of the invention dosages of components A, B and C can be set so low that their soil effect is optimally low. Thus, their

Use not only in sensitive cultures only possible, but groundwater contaminations are also virtually avoided. The inventive combination of active ingredients is a significant reduction of the necessary

Application rate of the active ingredients allows.

In the joint application of components A, B and C in the

agents according to the invention occur in a preferred embodiment as an improvement of the application profile superadditive (= synergistic) effects. The effect in the combinations is stronger than the expected sum of the effects of the individual herbicides used. The synergistic effects allow a higher and / or longer potency (lasting effect); the fight against a broader spectrum of weeds, grass weeds and cyperaceans, sometimes with only one or few applications; faster onset of herbicidal activity; Control of previously unrecognized species (gaps); Control, for example, of species that have tolerances or resistances to single or multiple herbicides;

Extension of the period of application and / or a reduction in the number of necessary individual applications or a reduction in the total amount applied and - as a result for the user - economically and ecologically more advantageous weed control systems.

The mentioned properties and advantages are in the practical

To control weed control in order to keep agricultural / forestry / horticultural crops, grassland / pastures or crops for energy production (biogas, bio-ethanol) free of undesired competing plants and thus to secure and / or increase yields qualitatively and quantitatively. The technical standard is due to these new combinations in the

herbicidal compositions according to the invention are significantly exceeded in terms of the properties described.

Although the herbicidal compositions according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.

In addition, the agents according to the invention can be partially

have growth-regulatory properties in crops. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as crop losses during storage can be reduced or completely prevented. Due to their improved application profile, the compositions of the invention can also be used to control harmful plants in known crops or to be developed tolerant or genetically engineered culture and

Energy crops are used. The transgenic plants (GMOs) are usually characterized by particular advantageous properties, for example, by resistance to certain pesticides, especially certain herbicides (such as resistance to the components A, B and C in the

inventive means), for example by resistances

Harmful insects, plant diseases or pathogens of plant diseases such as certain microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality,

Shelf life, as well as the composition 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 or increased vitamin content or energy properties are known. More special

Properties may be in tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.

Likewise, because of their herbicidal and other properties, the agents according to the invention can also be used for combating harmful plants in cultures of known or yet to be developed by mutant selection

Plants are used, and from crosses of mutagenic and transgenic plants.

Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist

for example, in classical breeding methods and the generation of mutants. Alternatively, new plants with altered properties can help

genetic engineering methods (see for example EP 0221044 A, EP 0131624 A). In several cases, for example, genetic engineering was described

Alterations of crops to modify the starch synthesized in the plants (eg WO 92/01 1376 A, WO 92/014827 A, WO 91/019806 A); transgenic crop plants which are resistant to certain glufosinate-type herbicides (cf., for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or against combinations or mixtures of these herbicides by gene stacking resistant, such as transgenic crops such as corn or soybean with the trade name or the name Optimum ™ GAT ™ (Glyphosate ALS Tolerant) transgenic

Crops, for example cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) that target the plants

Make pests resistant (EP 0142924 A, EP 0193259 A); transgenic

Crop plants with modified fatty acid composition (WO 91/013972 A); genetically engineered crops with new content or secondary substances, e.g. new phytoalexins which cause increased disease resistance (EP 0309862 A, EP 0464461 A); genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398 A); Transgenic crops that produce pharmaceutically or diagnostically important proteins ("molecular pharming"); transgenic crops that are characterized by higher yields or better quality; transgenic

Crop plants which are characterized by a combination e.g. the o.g. characterize new properties ("gene stacking").

Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; see, e.g. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431). For such genetic manipulations, nucleic acid molecules can be introduced into plasmids containing a

Mutagenesis or a sequence change by recombination of DNA sequences allow. By means of standard methods, e.g.

Base exchanges are made, partial sequences removed or natural or synthetic sequences added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see e.g. Sambrook et al., 1989, Molecular Cloning, A

Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996. 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

Cosuppressionseffekt.es or the expression of at least one appropriately engineered ribozyme, specifically transcripts of the above

Gene product splits.

For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. Also possible is the use of DNA sequences that have a high degree of homology to the coding

Have sequences of a gene product but are not completely identical.

In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. However, to achieve localization in a particular compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those of skill 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 expression of the nucleic acid molecules can also take place in the organelles of the plant cells.

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, i. both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available that changed

Have properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences. The present invention also provides a process for

Control of undesired plant growth (e.g.

preferably in crops such as cereals (e.g., hard and soft wheat, barley, rye, oats, crosses thereof such as triticale, planted or sown rice under 'upland' or 'paddy' conditions, corn, millet such as

Sorghum), sugar beet, cane, canola, cotton, sunflower, soya,

Potato, tomatoes, beans such as bushbeam and horse bean, flax, pasture grass, orchards, plantation crops, lawns and lawns, as well as residential and industrial sites, railway tracks, most preferably in monocotyledonous crops such as cereals, e.g. Wheat, barley, rye, oats,

Crosses thereof, such as triticale, rice, maize and millet, and dicotyledonous crops such as sunflower, soybean, potato, tomato, pea, carrot and fennel, wherein components A, B and C of the herbicidal compositions of the invention are taken together or separately, e.g. in pre-emergence (very early to late), post-emergence or pre-emergence, on the plants, e.g. Harmful plants, plant parts, plant seeds or the area on which the plants grow, e.g. applied the acreage.

The invention also provides the use of the herbicidal compositions according to the invention comprising the components A, B and C for controlling harmful plants, preferably in plant crops, preferably in the abovementioned plant crops. The invention furthermore also relates to the use of the herbicidal compositions according to the invention comprising components A, B and C for controlling herbicidally-resistant harmful plants (for example TSR and EMR resistances in ALS and ACCase), preferably in plant crops, preferably in the abovementioned crops.

The invention also provides the process with the herbicidal compositions according to the invention comprising the components A, B and C for the selective

Control of harmful plants in plant crops, preferably in the above-mentioned crops, and its use.

The invention also provides the method for controlling

undesired plant growth with the herbicidal compositions according to the invention containing the components A, B and C, as well as its use, in plant cultures which are genetically modified (transgenic) or by

Mutation selection were obtained, and which against growth substances, such. 2,4 D, dicamba or against herbicides containing essential plant enzymes, e.g.

Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or

Hydoxyphenylpyruvate Dioxygenases (HPPD) inhibit, respectively against herbicides from the group of sulfonylureas, glyphosate, glufosinate or

Benzoylisoxazole and analogues, or against any combination of these agents, are resistant. Particularly preferably, the

Herbicidal agents according to the invention are used in transgenic crops which are resistant to a combination of glyphosates and glufosinates,

Glyphosaten and sulfonylureas or imidazolinones are resistant. Most preferably, the herbicidal compositions of the invention in transgenic crops such. B. corn or soy with the trade name or the

Name Optimum ™ GAT ™ (Glyphosate ALS Tolerant).

The invention also provides the use of the herbicidal compositions according to the invention comprising the components A, B and C for controlling harmful plants, preferably in plant crops, preferably in the abovementioned plant crops.

The herbicidal compositions of the invention may also be non-selective to

Control of undesired plant growth, e.g. in

Plantation crops, on roadsides, squares, industrial plants or

Railway installations; or selectively used to control undesired plant growth in crops for energy production (biogas, bio-ethanol).

The herbicidal compositions according to the invention can be present both as mixed formulations of components A, B and C and optionally with further agrochemical active ingredients, additives and / or customary formulation auxiliaries which are then diluted with water in the customary manner, or as so-called tank mixtures by joint dilution the separately formulated or partially separately formulated components prepared with water become. Under certain circumstances, the blending formulations may be diluted with other liquids or solids or used undiluted.

The components A, B and C or their sub-combinations can be formulated in various ways, depending on which biological and / or chemical-physical parameters are given. As a general

Formulation options are for example: wettable powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions,

sprayable solutions or emulsions, suspension concentrates (SC),

Dispersions, oil dispersions (OD), suspoemulsions (SE), dusts (DP), mordants, granules for soil or litter application (GR) or

water-dispersible granules (WG), ultra-low-volume formulations,

Microcapsule or wax dispersions.

The individual formulation types are known in principle and will be

for example, described in: "Manual on Development and Use of FAO and WHO Specifications for Pesticides", FAO and WHO, Rome, Italy, 2002; Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker N.Y. 1973; K.

Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials, surfactants,

Solvents and other additives are also known and are described in, for example, Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridegewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986. On the basis of these formulations, it is also possible to prepare combinations with other agrochemical active substances, such as fungicides, insecticides, and safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix.

Spray powders (wettable powders) are uniformly dispersible in water

Preparations which, in addition to the active substances other than one or more diluents or inert substances, also contain ionic and / or nonionic surfactants (wetting agents, dispersants), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, propylene oxide-ethylene oxide copolymers, alkanesulfonates or alkylbenzenesulfonates or alkylnaphthalenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalene-sodium sulfonate or sodium oleoylmethyltaurine.

Emulsifiable concentrates are made by dissolving the active ingredients in one

organic solvent or solvent mixture, e.g. Butanol, Cydohexanon, dimethylformamide, acetophenone, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic and / or nonionic surfactants (emulsifiers) produced. Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide copolymers, alkyl polyethers, sorbitan fatty acid esters,

Polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

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

Formulation also be solved.

Oil dispersions are oil-based suspensions of active ingredients, where by oil is meant any organic liquid, e.g. As vegetable oils, aromatic or aliphatic solvents, or fatty acid alkyl esters. They can be prepared, for example, by wet milling using commercially available bead mills and, if appropriate, addition of further surfactants (wetting agents, dispersants), as described, for example, in US Pat. are already listed above for the other formulation types. In addition to the suspended drug or agents, other drugs in the

Formulation also be solved.

Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers from mixtures of water and water-immiscible organic solvents and optionally other surfactants, as described e.g. listed above for the other formulation types. The active ingredients are present in dissolved form.

Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying

Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites, chalk or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.

Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluidized bed, extruder and spray granules, see for example methods in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. See, for example, GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD Freyer, SA Evans, "Weed Control Handbook," for further details on pesticide formulation. 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations usually contain from 0.1 to 99

Percent by weight, in particular from 2 to 95% by weight, of active substances of the herbicidal components, the following concentrations being customary depending on the type of formulation: In wettable powders, the active compound concentration is e.g. about 10 to 95 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the drug concentration may be e.g. 5 to 80 wt .-%, amount. Dusty formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 0.2 to 25 wt .-% of active ingredient. In the case of granules such as dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.

In addition, the active substance formulations mentioned optionally contain the customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers,

Evaporation inhibitors and agents that affect the pH or viscosity.

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

Polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part. The fatty alcohol polyglycol ethers may be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates or phosphates, which are used, for example, as alkali salts (eg sodium and potassium salts) or ammonium salts, or else as alkaline earth salts such as magnesium salts, such as C 12 / _Ci-4 fatty alcohol diglykolethersulfat- sodium (Genapol ^® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity ", 227-232 (1988). Nonionic fatty alcohol polyglycol ethers are, for example, 2 to 20, preferably 3 to 15,

Ethylene oxide-containing (C10- Cis) -, preferably (Cio-Ci ₄₎ -Fettalkohol- 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 further comprises the combination of components A, B and C with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (For example, as fatty alcohol polyglycol ether) may be present. Preferred are

Ci ₂ / Ci fatty alcohol diglycol ether Nathum (Genapol ^® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3-15 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) as a penetration aid and

Are also suitable for a number of other herbicides, including herbicides from the series of imidazolinones (see, for example, EP-A-0502014).

The herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils. Under the term

Vegetable oils are 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, especially rapeseed understood, and their

Transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or Rapsolethylester.

The vegetable oils are preferably esters of C10-C22, preferably C12-C20 fatty acids. The C 10 -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 in particular cis-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid. Examples of Cio-C22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 -fatty acids, as contained for example in oils from oil-yielding plant species, or C 1 -C 20 -alkyl-C 10 -C 22 -fatty acid Esters, as can be obtained, for example, by transesterification of the abovementioned glycerol or glycol C 10 -C 22 -fatty acid esters with C 1 -C 20 -alcohols (for example methanol, ethanol, propanol or butanol). The transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.

Preferred C 1 -C 20 -alkyl-C 10 -C 22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters. As glycol and

Glycerol-Cio-C22-fatty acid esters preferred are the uniform or mixed glycol esters and glycerol esters of Cio-C22 fatty acids, especially those

Even numbered carbon fatty acids, e.g. 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 in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ^® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ^® B

(Novance, France, hereinafter 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. The present invention comprises in a further embodiment

Combinations of components A, B and C with the aforementioned

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 ^®, ^® Actirob B, Rako-Binol ^®, Renol ^® or Stefes Mero ^®.

For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-form preparations, soil or spreading granulates, as well as sprayable formulations are usually no longer diluted with further inert substances before use.

The active substances can be applied to the plants, plant parts, plant seeds or the acreage (field soil), preferably to the green plants and plant parts and optionally additionally to the field soil.

One possibility of application is the joint application of the active ingredients in the form of tank mixes, with the optimally formulated concentrated

Formulations of the individual active ingredients are mixed together in the tank with water and the resulting spray mixture is discharged.

A common herbicidal formulation of the herbicidal compositions according to the invention with the components A, B and C has the advantage of easier applicability, because the amounts of the components are already set in the correct ratio to each other. In addition, the adjuvants in the formulation can be optimally matched to one another. A. General Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a

Active substance / active ingredient mixture and 90 parts by weight of talc mixed as an inert material and comminuted in a hammer mill. b) A readily dispersible in water, wettable powder is obtained by adding 25 parts by weight of an active substance / active ingredient mixture, 64 parts by weight of kaolinhaltigen clay as inert material, 10 parts by weight of lignosulfonate potassium and 1 part by weight of oleoylmethyltaurine sodium as wetting and dispersing agent and ground in a pin mill.

An easily water-dispersible suspension concentrate is obtained by adding 20 parts by weight of an active substance / active substance mixture with 5 parts by weight of tristyrylphenol polyglycol ether (Soprophor BSU), 1 part by weight

Lignosulfonate sodium (Vanisperse CB) and 74 parts by weight of water mixed and ground in a ball mill to a fineness of less than 5 microns.

An easily dispersible in water oil dispersion is obtained by adding 20 parts by weight of an active ingredient / active ingredient mixture with 6 parts by weight

Alkylphenol polyglycol ether (Triton ^® X 207), 3 parts by weight

Isotridecanolpolyglykolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277 ° C) and mixed in a

Grinding ball mill to a fineness of less than 5 microns milled.

An emulsifiable concentrate is obtained from 15 parts by weight of an active substance / active substance mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

A water-dispersible granules are obtained by

75 parts by weight of an active ingredient / active substance mixture,

10 parts by weight of lignosulfonic acid calcium,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight kaolin

milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit.

A water-dispersible granule is also obtained by mixing 25 parts by weight of an active substance / active substance mixture,

5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,

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

17 parts by weight of calcium carbonate and

50 parts by weight of water

Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.

B. Biological Examples a) Method Descriptions

Greenhouse experiments

In the standard experiment, the seeds of different weeds and grass weeds were found in one with natural soil

Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm diameter seeded and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were placed on a laboratory sprayer with spray liquors containing the

inventive compositions, mixtures of the prior art or treated with the individually applied components. The application of the active ingredients or combinations of active substances formulated as WG, WP, EC or otherwise took place at the corresponding growth stages of the plants. The amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were placed back in the greenhouses.

About 3 weeks after the application, the soil or / and leaf action was evaluated visually according to a scale of 0-100% compared to an untreated control group: 0% = no discernible effect compared to the untreated control group; 100% = complete effect compared to the untreated control group. (Notes: The term "seed" also includes vegetative forms of propagation, such as rhizome pieces, abbreviations used: h light = hours

Lighting duration, g AS / ha = grams of active ingredient per hectare, l / ha = liters each

Hectares, S = sensitive, R = resistant)

1 . Pre-emergence weed effect: seeds of different weeds and weeds

Biotypes (origins) were found in one with natural soil

Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm diameter seeded and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were treated at BBCH stage 00-10 of the seeds / plants on a laboratory spray track with spray mixtures with the agents according to the invention, mixtures or with the individually used components as WG, WP, EC or other formulations. The

Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. 2. Post-emergence weed action: Seeds of different weeds and weed biotypes (origins) were grown in one with natural soil

Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm diameter seeded and covered with a covering layer of the soil of about 1 cm. The pots were then cultivated in a greenhouse (12-16h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were grown at different BBCH stages between 11-25 seeds / plants, i. usually between two to three weeks after the beginning of the cultivation, on a laboratory spray lane with spray liquors with the

agents, mixtures or treated with the individually applied components as WG, WP, EC or other formulations. The amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. Pre-emergence selectivity: seeds of different crops

(Origins) were seeded in a pot of 8-13 cm diameter filled with natural soil of a standard field soil (loamy silt; non-sterile) and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were in the BBCH stage 00-10 of the seeds / plants on a laboratory sprayer with spray mixtures with the compositions of the invention, mixtures or with the individually applied components as WG, WP, EC or others

Treated formulations. The amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. Postemergence selectivity: Seeds of different crops

(Origins) were seeded in a pot of 8-13 cm diameter filled with natural soil of a standard field soil (loamy silt; non-sterile) and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were added to different BBCH stages 1 1 -32 of the seeds / plants, i. usually between two to four weeks after the beginning of the breeding, on one

Laboratory spray booth with spray mixtures with the agents according to the invention,

Treated mixtures or with the individually applied components as WG, WP, EC or other formulations. The

Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) weed action in the pre- and post-emergence at different

Cultivation conditions: seeds of different weeds and grass

Biotypes (origins) were found in one with natural soil Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm diameter seeded and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray

agents, mixtures or treated with the individually applied components as WG, WP, EC or other formulations. The amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). The irrigation was varied according to the question. The individual comparison groups were graded in a range from above the PWP (permanent wilting point) and up to the level of the maximum

Field capacity supplied with water. Weed effect in pre- and post-emergence at different

Irrigation conditions: Seeds of different weeds and weed biotypes (origins) were found in one with natural soil

Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm diameter seeded and covered with a covering layer of the soil of about 1 cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray

agents, mixtures or treated with the individually applied components as WG, WP, EC or other formulations. The amount of water used for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C). The individual comparison groups were different Exposed to irrigation techniques. Irrigation was done either from below or in increments from above (simulated irrigation).

Weed effect in pre- and post-emergence at different

Soil conditions: seeds of different weeds and weed Biotypes (origins) were seeded in a natural soil filled pot of 8-13 cm diameter and covered with a cover layer of the soil of about 1 cm. For a comparison of herbicidal activity, the plants were cultured in different cultivation soil, from a sandy soil to heavy clay soil and various organic substance contents. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were grown to different BBCH stages 00-25 of the seeds / plants on one

Water application rate for the spray application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C).

Pre and postemergence weed action to control resistant weed / weed species: Seeds of different weeds and weed Biotypes (origins) with different resistance mechanisms to different

Mechanisms of action were in one with natural earth

Standard field soil (loamy silt, non-sterile) seeded pot of 8-13 cm in diameter and covered with a covering layer of soil of about 1 cm .. The pots were then placed in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were seeded to different BBCH stages 00-25 of the seeds / plants on a laboratory sprayer with the spray

inventive compositions, mixtures or with the individually applied components as WG, WP, EC or other formulations treated. The amount of water used for the application was 100-600 l / ha. After treatment, the plants were again placed in the greenhouses and fertilized and watered as needed. The pots were cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C).

9. weed effect and culture selectivity in the pre- and postemergence at

Different sowing conditions: seeds of different weeds, weed biotypes (origins) and crops (origins) were seeded in a natural soil filled pot of 8-13 cm in diameter and covered with a cover layer of the soil of about 0-5cm. The pots were then cultured in a greenhouse (12-16 h light, temperature day 20-22 ° C, night 15-18 ° C) until the time of application. The pots were grown to different BBCH stages 00-25 of the seeds / plants on one

field trials

In field trials were under natural conditions in practice

Field preparation and with natural or artificial contamination with

Harmful plants before or after sowing the crops or before or after emergence of the harmful plants, the compositions of the invention, mixtures of the prior art or the individual components applied and in the period of 4 weeks to 8 months after treatment compared to

untreated sections (parcels) visually scored. The were

Damage to crops and the effect against harmful plants recorded as a percentage, as well as the other effects of each test question. b) Results

The following abbreviations were used: BBCH = BBCH code provides information about the morphological developmental stage of a plant. The abbreviation stands officially for the Federal Biological Research Center, Federal Plant Variety Office and Chemical Industry. The range of BBCH 00-10 stands for the stages of germination of the seeds until the surface is pierced. The range of BBCH 1 1 -25 stands for the stages of the sheet development up to the

Assembly (according to the number of tillers or side shoots).

PE = pre-emergence application on the ground; BBCH of seeds / plants 00-10.

PO = postemergence application to the green plant parts; BBCH of plants 1 1 - 25.

HRAC = 'Herbicide Resistance Action Committee', which classifies the approved active substances according to their mode of action (MoA). HRAC group A = acetylcoenzyme A carboxylase inhibitors (MoA: ACCase).

HRAC group B = acetolactate synthase inhibitors (MoA: ALS).

AS = active substance (based on 100% active ingredient, syn. A.i. (English)). Dose g AS / ha = application rate in grams of active substance per hectare.

For the designation of the respective ryegrass biotypes in the results, the botanical names, i.a. Lolium spp. (LOLSS), Lolium multiflorum (LOLMU), Lolium perenne (LOLPE) (in brackets: EPPO code or former Bayer code).

The effects of the herbicidal compositions according to the invention correspond to the stated requirements and thus solve the object of improving the Application profile of the herbicidal active ingredient Aclonifen (including providing more flexible solutions in relation to the necessary application rates with constant to increased efficacy). As far as herbicidal effects of the agents according to the invention in comparison with mixtures of the prior art or with individually applied components against economically important monocotyledonous and dicotyledonous harmful plants were in focus, the synergistic herbicidal effects using the 'Colby formula' (see SR Colby, Weeds 15 (1967), 20-22):

E ^c = (A + B + C) - (AxB + + AxC BxC) / 100 + (AxBxC) / 10000 which means:

A, B, C = in each case the effect of the components A or B or C in percent at a dosage of a or b or c gram AS / ha;

E ^c = expected value according to Colby in% at a dosage of a + b + c gram AS / ha.

Δ = difference (%) from measured value (%) to expected value (%)

(measured value minus expected value).

Evaluation: - measured values: in each case for (A), (B) and (C) and (A) + (B) + (C) in%.

Rating: - measured value (%) greater> than E ^c : synergism (+ Δ). - measured value (%) equals = E ^c : £ additive effect (± 0Δ).

- measured value (%) less <than E ^c : antagonism (-Δ). Table 1: Comparison of the effect of the mixture on different ryegrass biotypes - greenhouse experiment; Post-emergence treatment (PO, BBCH 1 1).

Chlortoluron and BRODAL for Diflufenican; (1) Comparative product for representing the existing resistance in the different biotypes.

In the investigated plant species, a clear synergistic effect against the resistant biotypes of HRAC groups A and B could be detected by the mixture (Δ + 27% and Δ + 5.6%, respectively).

In addition, during the postemergence treatment with the mixture an increased synergistic effect could be detected in the non-resistant biotype (Δ + 7.5%).

Claims

claims:

1 . Herbicidal agents containing as the only herbicidally active ingredients

A) Aclonifen (component A),

B) chlorotoluron (component B) and

C) diflufenican (component C).

2. A herbicidal composition according to claim 1, wherein the herbicidal components are in the weight ratio indicated below:

preferably (1-25) :( 1-25) :( 0.5-50),

particularly preferred (1-10) :( 1-10) :( 1-10).

3. A herbicidal composition according to claim 1 or 2, containing for the respective

Herbicidal components indicated below

Component A: generally 10 to 5000 g AS / ha, preferably 80 to 3000 g

AS / ha, more preferably 80-1000 g AS / ha aclonifen;

Component C: in general 1-500 g AS / ha, preferably 10-300 g AS / ha, more preferably 30-200 g AS / ha diflufenican.

4. A herbicidal composition according to any one of claims 1 to 3, additionally containing customary in plant protection additives and / or formulation auxiliaries.

5. A herbicidal composition according to any one of claims 1 to 4, additionally containing one or more further components from the group of agrochemical active substances comprising insecticides, fungicides and safeners.

6. Use of the defined according to any one of claims 1 to 5 herbicidal compositions for controlling harmful plants.

7. Use of the defined in any one of claims 1 to 5 herbicidal compositions for controlling herbicide-resistant harmful plants.

8. A method for controlling undesired plant growth, wherein the components A, B and C of the herbicidal agents, defined according to one of

Claims 1 to 5, applied together or separately to the plants, plant parts, plant seeds or the area on which the plants grow.

9. The method of claim 8 for the selective control of harmful plants in crops.

10. The method of claim 9, wherein the crops have been genetically engineered or obtained by mutation selection.