EA042398B1 - 5-FLUORO-4-IMINO-3-(ALKYL/SUBSTITUTED ALKYL)-1-(ARYLSULFONIL)-3,4-DIHYDROPYRIMIDIN-2(1H)-OH AS A SEED TREATMENT - Google Patents

Description

The field of technology to which the invention belongs

The invention relates to methods for controlling phytopathogenic fungi by treating seeds or seedlings of a plant with a novel seed treatment fungicide.

State of the art

In agriculture, seed treatment or seed dressing is used to treat seeds before sowing. The term seed treatment includes all usable seed treatment technologies known in the art, such as seed dressing, seed coating, seed dusting, seed inhibition (soaking), seed foaming (i.e., foam coating), and seed granulation, and it preferably refers to applying the fungicidally active compound(s) directly to the seeds themselves prior to sowing and/or in their immediate vicinity during sowing.

The essence of the invention

One embodiment of the invention includes a method of treating a plant seed or seedling to prevent or control a fungal plant pathogen infestation of a plant, wherein the method comprises treating the plant seed or seedling with a compound of formula ^I0

HN^N^O ι R ₂

I where each R1 and R2 represents -CH ₃ .

In a specific embodiment of the above embodiment, the compound of formula I is applied at a rate of 3.7 to 300 grams per 100 kilograms of seeds.

In one illustrative embodiment, a method is provided for protecting a plant from plant infestation by a fungal pathogen, comprising applying a compound of Formula I as a liquid or solid formulation to a seedling environment.

E - C -

HN^N^O

I r ₂ ι

where each R ₁ and R ₂ represents -CH ₃ .

In another more specific embodiment of the above embodiment, the composition further comprises an auxiliary surfactant selected from the group consisting of ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, salts of sulfosuccinic acid esters, ethoxylated organosilicon compounds, ethoxylated fatty amines, and mixtures of surface -active substances with mineral or vegetable oils.

In another more specific embodiment of any of the above embodiments:

a) a compound of formula I is applied at a rate of 0.5 to 500 grams per 100 kilograms of seeds;

b) the seed or seedling being treated is wheat seed (Triticum sp.; TRZSS), sugar beet (BEAVA) or groundnut (ARHHY), and/or

c) the fungal pathogen is selected from the group consisting of wheat border leaf spot (Zymoseptoria tritici), sugar beet leaf spot (Cercospora beticola) and peanut leaf spot (Cercospora arachidicola and Cercosporidium personatum).

In another embodiment, a seed or seedling of a plant adapted to prevent or control a fungal plant pathogen from attacking a plant by the method described above is provided.

In another embodiment, the use of a compound of formula I is provided.

- 1 042398 for the manufacture of a composition for treating seeds or seedlings of a plant for preventing plant damage by a fungal pathogen or controlling a fungal pathogen of a plant, where each R1 and

R2 is -CH ₃ .

In another embodiment, the use of a compound of formula I is provided.

for the manufacture of a composition in the form of a liquid or solid composition for treating the environment of seedlings to protect the plant from attack by a fungal pathogen, where each R ₁ and R ₂ represents -CH3.

In another embodiment, a composition is provided comprising a compound of formula I

and an auxiliary surfactant selected from the group consisting of ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, sulfosuccinic acid esters, ethoxylated organosilicon compounds, ethoxylated fatty amines, and mixtures of surfactants with mineral or vegetable oils, for seed treatment or seedlings of a plant to prevent or control a fungal pathogen, wherein R ₁ and R ₂ are each —CH ₃ .

In another more specific embodiment of the above embodiment:

a) the composition is a tank mix, or

b) the composition is a wettable powder, water-dispersible granules, emulsifiable concentrate, aqueous suspensions, suspended concentrate, aqueous emulsion, emulsion in water, or emulsion suspension.

In another embodiment, a method is provided for treating a seed or seedling of a plant to prevent or control a fungal pathogen of a plant, the method comprising treating the seed or seedling of a plant with the above composition.

In another embodiment, a method is provided for protecting a plant from a plant attack by a fungal pathogen, comprising applying the above composition in the form of a liquid or solid composition to the seedling environment.

Additional features and advantages of the present invention will become apparent to those skilled in the art upon consideration of the following detailed description of illustrative embodiments illustrating the best mode for realizing the benefits described herein as currently expected.

Detailed description of the invention

The embodiments of the invention described herein are not intended to be exhaustive or to limit the invention to the specific forms described. Rather, the embodiments selected for description are chosen to enable those skilled in the art to carry out the invention.

Seed treatment may independently include applying a compound of formula I directly to the seed as a coating, or exposing the seed to the environment as a liquid or solid formulation. In addition, the compound of formula I can be applied as a liquid or solid formulation to the seedling environment.

Seeds are interpreted broadly to include any object that can be sown and can potentially be planted in situ (in soil) to grow crops. The term seed encompasses seeds and sprouts of plants of all kinds, including, but not limited to, whole seeds, seed pieces, grains, root shoots, corms, bulbs, fruits, tubers, clothespins, cut bushes and similar forms, and preferably means whole seeds.

Seedlings are germinated seeds.

The seedling environment is the soil or other growth medium surrounding the seedling.

The present invention encompasses all carrier media with which a compound of formula I can be prepared for delivery and use as a seed treatment fungicide. Conventional seed treatment formulations include, for example, flowable concentrates, solutions, dry treatment powders, water-dispersible slurry treatment powders, water-soluble powders, and formulations in the form of emulsions and gels. These formulations may be applied diluted or undiluted.

Typically, formulations are applied after diluting the concentrated formulation with water, in the form of aqueous solutions, suspensions or emulsions, or combinations thereof. Such solutions, suspensions or emulsions can be prepared from water-soluble, water-suspendable or emulsifiable formulations or combinations thereof, which are in solid form, these include and are commonly known as wettable powders or water-dispersible granules; or liquids, these include and are commonly known as emulsifiable concentrates, aqueous suspensions or suspended concentrates, and aqueous or emulsions in water, or mixtures thereof, such as suspension emulsions. As will be apparent, any material to which this composition may be added may be used, provided that it produces the desired beneficial effect without significantly adversely affecting the desired activity of the pesticidally active ingredients as pesticidal agents, improves retention time, or reduces the effective concentration required to achieve pesticide exposure.

Wettable powders, which can be compacted to form water-dispersible granules, contain a finely mixed mixture of one or more pesticidally active ingredients, an inert carrier, and surfactants. The concentration of the pesticidally active ingredient in the wettable powder is typically from about 10 percent to about 90 percent by weight based on the total weight of the wettable powder, more preferably from about 25 percent by weight to about 75 percent by weight. When preparing wettable powder formulations, pesticidally active ingredients may be compounded with any finely divided solid product such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earth, purified silicates or something similar. In such operations, the finely divided carrier and surfactants are typically mixed with the compound(s) and ground.

Emulsifiable pesticide active ingredient concentrates contain a typical concentration, eg, from about 10 weight percent to about 50 weight percent, of the pesticide active ingredient, in an appropriate liquid, based on the total weight of the concentrate. The pesticidally active ingredients are dissolved in an inert carrier which is either a water-miscible solvent or a mixture of water-immiscible organic solvents and emulsifiers. The concentrates can be diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions. Suitable organic solvents include aromatic compounds, in particular high boiling naphthalene and olefinic parts of the oil, such as heavy aromatic naphtha. Other organic solvents may also be used, such as, for example, terpene solvents, including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.

Emulsifiers that can advantageously be used herein can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a mixture of two or more emulsifiers. Examples of nonionic emulsifiers suitable for use in the preparation of emulsifiable concentrates include polyalkylene glycol ethers and condensates of alkyl and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide, such as ethoxylated alkylphenols and esters of carboxylic acids esterified with a polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts (eg, with calcium) of alkylarylsulfonic acids, oil-soluble ether salts of sulfated polyglycols, and the corresponding phosphated polyglycol ether salts.

Representative organic liquids that can be used in the preparation of emulsified concentrates are aromatic liquids such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, in particular dimethylamides; and glycol ethers such as n-butyl ether, ethyl ether or diethylene glycol methyl ether, and triethylene glycol methyl ether, and the like. Mixtures of two or more organic liquids can also be used in the preparation of an emulsifiable concentrate. Organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some instances. Surface active dispersing agents are typically used in liquid formulations in an amount of 0.1 to 20 weight percent based on the combined weight of the emulsifying agents. The compositions may also contain other compatible additives, such as plant growth regulators, and other biologically active compounds used in agriculture.

Aqueous suspensions contain suspensions of one or more water-insoluble pesticidally active ingredients dispersed in an aqueous carrier medium at a concentration ranging from about 5 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding one or more pesticidally active ingredients and thoroughly mixing the ground material in a carrier medium consisting of water and surfactants selected from the same types discussed above. Other components, such as inorganic salts and synthetic or natural resins, may also be added to increase the density and viscosity of the aqueous carrier medium. Often the most effective is grinding and mixing, simultaneously, by preparing an aqueous mixture and homogenizing it in equipment such as a sand mill, ball mill or piston-type homogenizer.

Aqueous emulsions comprise emulsions of one or more water-insoluble pesticidally active ingredients emulsified in an aqueous carrier medium at a concentration typically in the range of from about 5 to about 50 weight percent, based on the total weight of the aqueous emulsion. If the pesticidally active ingredient is a solid, it must be dissolved in an appropriate water-immiscible solvent before making up an aqueous emulsion. Emulsions are prepared by emulsifying the liquid pesticide active ingredient or a water-immiscible solution thereof in an aqueous medium, typically with the addition of surfactants that help form and stabilize the emulsion, as described above. This is often achieved with vigorous mixing provided by high shear mixers or homogenizers.

The compositions of the present invention may also be granular formulations, which are particularly suitable for use in soil applications. Granular formulations typically contain from about 0.5 to about 10 weight percent, based on the total weight of the granular formulation, of pesticidally active ingredient(s) dispersed in an inert carrier that consists wholly or in large part of coarsely divided inert material such as attapulgite, bentonite, diatomaceous earth, clay or similar inexpensive material. Such formulations are typically prepared by dissolving the pesticide active ingredients in a suitable solvent and applying them to a granular carrier that has been preformed into appropriate particle sizes ranging from about 0.5 to about 3 mm. A suitable solvent is one in which the compound is substantially or completely soluble. Such formulations can also be prepared by preparing a dough or paste from the carrier and compound and solvent, and grinding and drying to obtain the desired granular particles.

Dust can be prepared by finely mixing one or more pesticidally active ingredients in powder form with an appropriate pulverulent agronomic carrier such as, for example, kaolin clay, pulverized volcanic rock, talc, pulverized bark, and the like. Dusts may suitably contain from about 1 to about 10 weight percent compounds relative to the total weight of the dust.

The formulations may additionally contain co-surfactants and polymers to enhance adhesion and flow and to reduce dusting of the active ingredients. These adjuvants may optionally be used as a formulation component or as a tank mix. The amount of co-surfactant may generally vary from 0.01 to 1.0 percent by volume based on the volume of water sprayed, preferably from 0.05 to 0.5 percent by volume. Suitable auxiliary surfactants include, but are not limited to, ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, sulfosuccinic acid ester salts, ethoxylated organosilicon compounds, ethoxylated fatty amines, and mixtures of surfactants with mineral or vegetable oils. The formulations may also include oil-in-water emulsions such as those described in US Patent Application Serial No. 11/495228, the disclosure of which is expressly incorporated herein by reference.

The compounds of formula I are effective when used on plants in an inhibitory manner.

- 4 042398 disease and phytologically acceptable amount. The term disease-inhibiting and phytologically acceptable amount refers to an amount of a compound that kills or inhibits a plant disease for which such treatment is desirable, but is not significantly toxic to the plant. This amount will typically be from about 0.5 to about 500 g.a. i. / 100 kg of seeds. The exact amount of a compound of formula I that is needed varies with the fungal disease to be prevented, the type of formulation used, method of application, time schedule for application, particular plant species, climatic conditions, and the like. The dilution and application rate will depend on the type of equipment used, the method and frequency of application desired, and the diseases to be prevented.

Another embodiment of the present invention is a method for controlling or preventing fungal attack. This method comprises applying to the seed a fungicidally effective amount of a compound of formula I. The compound of formula I is useful in treating a variety of plants at fungicidal levels while exhibiting low phytotoxicity. The compound can be used both as a dressing agent and/or as an eradicant.

The compounds of formula I have been found to have significant fungicidal effects, in particular for agronomic use. The compounds of formula I are particularly effective for use in crops and horticultural plants. Additional benefits may include, but are not limited to, improved crop protection; improving the yield from the plant (for example, increasing the biomass and/or increasing the content of valuable ingredients); improving plant vitality (eg, improving plant growth and/or greening of leaves); improving the quality of the plant (eg, improving the content or composition of certain ingredients); and improving the tolerance of the plant to abiotic and/or biotic stress.

Those skilled in the art will appreciate that the efficacy of the compounds of formula I against the following fungi establishes the overall usefulness of the compounds as fungicides.

The compounds of formula I have broad ranges of activity against fungal pathogens. Illustrative pathogens may include, but are not limited to, wheat banded leaf spot (Zymoseptoria tritici), sugar beet leaf spot (Cercospora beticola), peanut leaf spot (Cercospora arachidicola and Cercosporidium personatum). The exact amount of active material to be applied depends not only on the specific formulation to be applied, but also on the specific action desired, on the fungal species to be controlled and on its growth stage, and on the part of the plant or other product which must come into contact with the connection.

Any range or desired value given herein may be expanded or changed without losing the impacts under consideration, as will be apparent to those skilled in the art upon understanding the concepts of this document.

Examples.

Evaluation of fungicidal activity in the form of a seed treatment against banded leaf spot of wheat (Zymoseptoria tritici; Bayer code SEPTTR): wheat seeds of the cultivar Yuma are treated with seed dye and a composition of 10% suspension of compound 1 concentrate at a flow rate of 300, 100, 33.3, 11, 3.7 and 0 grams of active ingredient / 100 kilograms of seeds (g a.i. / 100 kg of seeds). The treated seeds are sown in pots containing 50% mineral soil/50% soil-free Metro plant mix 12 days after treatment, 10 seeds per pot, and grown in a greenhouse at 20°C. Four pots of 7 day old seedlings are inoculated with an aqueous suspension of Z. tritici spores and after inoculation the plants are kept at 100% relative humidity to allow the spores to germinate and infect the leaves. The plants are then transferred to a greenhouse maintained at 20°C for disease development.

The activity of various compounds of formula I, when evaluated in these experiments, are presented in table. 2. The effectiveness of the compounds of formula I in controlling diseases is determined by assessing the severity of the disease on the treated plants, then converting this assessment of severity into a percentage of control relative to the level of the disease on the untreated inoculated plants.

The results of the studies show that compound 1 is very active against Z. tritici, providing 93% control of the disease at a consumption of 11 g a. i. / 100 kg of seeds.

Foliar disease control with these seed treatment applications demonstrates that the test compound enters the xylem and is redistributed to the leaves in an amount sufficient to allow the treatment to prevent the disease after seed treatment. In addition, there is no evidence of growth retardation or phytotoxicity after Compound 1 application, even at the highest flow rate tested. Excellent disease prevention without phytotoxicity indicates that the chemical classes represented by the compounds of formula I have potential beneficial effects as a seed treatment.

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Claims (12)

Table 1 Biological Activity Rating Scale Prevention of leaf disease by seed treatment using a compound of formula I Comm. No.* Ri r ₂ Consumption (g a.i./100 kg seeds)* SEPTTR* 1 CH ₃ CH ₃ 300 A 100 A 33.3 A eleven A 3.7 D * Conn. No - connection number; * g a. i. / 100 kg of seeds - grams of active ingredient per 100 kilograms of seeds; SEPTTR - banded leaf spot of wheat (Zymoseptoria tritici). CLAIM 1. A method of treating a plant seed or seedling to prevent or control a fungal plant pathogen infestation of a plant, wherein the method comprises treating the plant seed or seedling with a compound of formula I where each R1 and R2 represents -CH3. 2. A method of protecting a plant from plant damage by a fungal pathogen, comprising applying a compound of formula I in the form of a liquid or solid composition to the seedling environment, where each R ₁ and R ₂ represents -CH ₃ . 3. The method according to claim 1 or 2, in which: a) a compound of formula I is applied at a rate of 0.5 to 500 grams per 100 kilograms of seeds; b) the seed or seedling being treated is wheat seed (Triticum sp.; TRZSS), sugar beet (BEAVA) or groundnut (ARHHY), and/or c) the fungal pathogen is selected from the group consisting of wheat border leaf spot (Zymoseptoria tritici), sugar beet leaf spot (Cercospora beticola) and peanut leaf spot (Cercospora arachidicola and Cercosporidium personatum). 4. The method according to claim 1, wherein the compound of formula I is applied at a rate of 3.7 to 300 grams per 100 kilograms of seeds. - 6 042398 5. The method of claim 2, wherein the formulation further comprises an auxiliary surfactant selected from the group consisting of ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, sulfosuccinic acid ester salts, ethoxylated organosilicon compounds, ethoxylated fatty amines, and mixtures of surfactants. active substances with mineral or vegetable oils. 6. Seeds or seedlings of a plant adapted to prevent or control a fungal pathogen of a plant, treated by the method of π. 1. 7. Use of a compound of formula I I for the manufacture of a composition for treating seeds or seedlings of a plant for preventing or controlling a plant fungal pathogen, wherein Ri and R ₂ are each —CH ₃ . 8. Use of a compound of formula I I for the manufacture of a composition in the form of a liquid or solid composition for treating the environment of seedlings to protect the plant from attack by a fungal pathogen, where each Ri and R ₂ represent -CH ₃ . 9. Composition containing a compound of formula I HN^N^O I r ₂ I and an auxiliary surfactant selected from the group consisting of ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, salts of sulfosuccinic acid esters, ethoxylated organosilicon compounds, ethoxylated fatty amines and mixtures of surfactants with mineral or vegetable oils, for processing seeds or seedlings of a plant to prevent or control a fungal pathogen, wherein Ri and R ₂ are each —CH ₃ . 10. Composition according to claim 9, where: a) the composition is a tank mix, or b) the composition is a wettable powder, water-dispersible granules, emulsifiable concentrate, aqueous suspensions, suspended concentrate, aqueous emulsion, emulsion in water or emulsion suspension. 11. A method of treating a plant seed or seedling to prevent or control a fungal plant pathogen infestation of a plant, wherein the method comprises treating the plant seed or seedling with the composition of claim 9. 12. A method of protecting a plant from a plant attack by a fungal pathogen, comprising applying the composition according to claim 9 in the form of a liquid or solid composition to the seedling environment. Eurasian Patent Organization, EAPO Russia, 109012, Moscow, Maly Cherkassky per., 2