WO2014001357A1 - Herbicidal agents containing flufenacet - Google Patents

Herbicidal agents containing flufenacet Download PDF


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WO2014001357A1 PCT/EP2013/063314 EP2013063314W WO2014001357A1 WO 2014001357 A1 WO2014001357 A1 WO 2014001357A1 EP 2013063314 W EP2013063314 W EP 2013063314W WO 2014001357 A1 WO2014001357 A1 WO 2014001357A1
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German (de)
French (fr)
Dominique Schreiber
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Bayer Cropscience Ag
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Priority to DE102012211036.4 priority
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Publication of WO2014001357A1 publication Critical patent/WO2014001357A1/en



    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms


The invention relates to herbicidal agents comprising an effective amount of flufenacet and the further herbicide aclonifen. Said herbicidal agents have an improved range of application.


 Description Herbicidal agent containing flufenacet

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 Flufenacet and another herbicide.

The herbicidal active ingredient Flufenacet (manufacturer: Bayer CropScience) belongs to the group of heteroaryloxy-acetamides and mixtures of this group with other herbicides are known from the literature: for example (for example) US 5945397 B, US 5593942 B, US 581 1373 B, US 6967188 B. In US 5858920 B among others

 Heteroaryloxy-acetamides in admixture with single agents, e.g. the herbicide Aclonifen, but without experimental data for the

synergistic effect. The herbicidal active ingredient flufenacet is characterized by a broad activity against monocotyledonous and dicotyledonous harmful plants and is used e.g. used in pre-sowing, pre-emergence or postemergence agriculture in sown and / or planted agricultural or horticultural crops and non-crops (eg in cereals such as wheat, barley, rye, oats, triticale, rice, corn, millet, sugar beet, sugarcane, Oilseed rape, cotton, sunflower, soya, potato, tomatoes, beans, flax, pasture grass, fruit growing plants, plantation crops, green areas and lawns, as well as residential and industrial sites, railway tracks).

As an individual active ingredient, Flufenacet is commercially available, for example, under the trade names Cadou®, Drago®, Define® and Tiara®. In addition to using the

 Single agents are also known from mixtures of flufenacet with other herbicides (for example US 5985797 B, US 5912206 B, US 6492301 B, US 6864217 B, US 6486096 B, US 2003/0069138 A, WO 2002/058472 A, US 6365550 B, US Pat.

US 2003/0060367 A, US 6878675 B, US 6071858 B, WO 2007/112834 A) and in Trade: Mixture with metribuzin (eg Axiom®, Bastille®, Artist®, Domain®,

Plateen®, Fedor®, Draeda®), with isoxaflutole (eg Epic®, Cadou Star®), with metosulam (eg Diplome®, Terano®), with diflufenican (eg Herold®, Liberator®), with 2,4-D (eg Drago 3.4®), with atrazine (eg Aspect®), with pendimethalin (eg

Crystal®, Malibu Pack®), with atrazine and metribuzin (e.g., Axiom AT®) and with diflufenican and flurtamones (e.g., Baccara FORTE®).

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

Areas of application, increasing crop plant tolerance, reaction to new production techniques in individual crops and / or 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 '(Abbreviation: TSR;

Weed populations contain biotypes with a site-specific resistance, i. by natural mutations in the gene sequence, the binding site changes at the site of action, so that the drugs no longer or insufficiently bind and act accordingly) and 'Enhanced Metabolism Resistance' (abbreviation: EMR: where the weed populations contain biotypes with a metabolic resistance, ie the plants possess the ability of 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): eg HRAC group A = acetylcoenzyme 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 agents. However, phenomena of physical and biological phenomena often occur in the combined use of several active substances

Incompatibility, e.g. lack of stability in a coformulation, decomposition of an active substance or antagonism of the active ingredients. On the other hand, combinations of active substances having a favorable action profile, high stability and, if possible, synergistically enhanced action, which are associated with a reduction in the active ingredient, are desirable

Application rate compared to the single application of the active ingredients to be combined allowed. Also desirable are combinations of drugs that the

Increase crop plant tolerance in general and / or special

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 Flufenacet with regard to:

 a simplified application method, which reduces the costs for the

 Reduce users and thus would have a gentler impact on the environment.

 - An improvement in the application flexibility of the active ingredients from Voraufiauf to postemergence of the crop and weed plants.

 an improvement and application flexibility of the effect safety on soils with different soil properties (e.g.

 Soil moisture).

- an improvement of the efficacy of resistant weed species, which would allow a new possibility for an effective resistance management; the last mentioned task was in the foreground.

This object has been achieved by providing herbicidal compositions containing flufenacet and the further herbicide aclonifen.

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

 A) flufenacet (component A),

 B) Aclonifen (component B).

The active ingredients mentioned in this description with their "common name"

(herbicidally active ingredients) are, for example, from "The Pesticide Manual", 14th Edition 2006/2007, or in the corresponding "The e-Pesticide Manual", Version 4.0 (2006-07), each published by the British Crop Protection Council and the Royal Soc. of Chemistry, and known from "The Compendium of Pesticide Common Names" on the Internet (http://www.alanwood.net/pesticides/).

The herbicidally active components component A and B 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", 14th edition (s.o.) and have the following

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

Entry number / "sequential entry number"): - Component A: Flufenacet (PM # 381), syn. thiafluamide, e.g. N- (4-fluorophenyl) -N- (1-methylethyl) -2 - [[5- (trifluoromethyl) -1, 3,4-thiadiazol-2-yl] oxy] acetamide;

 Component B: Aclonifen (PM # 9), e.g. 2-chloro-6-nitro-3-phenoxybenzenamine.

If the short form of the "common name" of an active ingredient is used in the context of this description, then - if applicable - are all common Derivatives, such as the esters and salts, and isomers, in particular optical isomers, 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 and B and may contain further constituents, e.g. agrochemical active substances from the group of insecticides, fungicides and safeners and / or additives and / or formulation auxiliaries customary in crop protection, 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. Preferred is the common or timely application of the active ingredients of the invention

Herbicidal agents.

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 15 to 7000 g AS / ha of 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:

 (Area component A): (area component B)

 in general (2 - 400): (1 - 100),

 preferably (1-10): (1-25),

 particularly preferred (1-5): (1-10).

The application rates of the respective herbicidal components in the herbicidal composition are: Component A: in general 5-2000 g AS / ha, preferably 30-400 g

 AS / ha, more preferably 50-300 g AS / ha flufenacet;

 Component B: generally 10 to 5000 g AS / ha, preferably 80 to 3000 g AS / ha, more preferably 80 to 1000 g AS / ha aclonifen. Accordingly, from the above-mentioned application rates

Percent by weight (% by weight) of the herbicidal components based on the Total weight of herbicide center! calculated, which may also contain other ingredients.

The herbicidal compositions of the present invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds, such as weeds, grass weeds or cyperaceans, including species resistant to herbicidal active compounds, e.g. Glyphosate, glufosinate, atrazine, photosynthesis inhibitors, imidazolinone herbicides, sulfonylureas, (hetero) aryloxy-aryloxyalkylcarboxylic acids or -phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedione oximes (so-called 'dims') or auxin inhibitors. Hard-to-control perennial weeds that sprout out of rhizomes, rhizomes or other endemic organs are also well recognized by the active ingredients. The substances may be e.g. be applied in pre-sowing, pre-emergence or post-emergence, e.g. together 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. Ave na 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.

In dicotyledonous weed species, the spectrum of activity extends to species such as e.g. 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 annuel! page as well as Convolvulus, Cirsium, Rumex and Artemisia in perennial weeds.

Are the herbicidal compositions of the invention before germination on the

Applied to the earth's surface, 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. 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 and B can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contamination is also virtually avoided. The combination of active substances according to the invention enables a considerable reduction in the required application rate of the active substances.

In the joint application of components A and B in the

agents according to the invention occur in a preferred embodiment as an improvement of the application profile superadditive (= synergistic) effects. It is the Effect in the combinations 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 control of a broader spectrum of weeds, grass weeds and cyperaceans, sometimes with only one or a few applications; faster onset of herbicidal activity; Control of p