Fungicidal composition and method for inhibiting the growth of fungus in the lesion

 

(57) Abstract:

Describes the concentrated liquid fungicidal composition based on compounds of formula (Ia) (metconazole):

and method of inhibiting the growth of fungus in the lesion, which involves applying a synergistic effective amount of metconazole and CHLOROTHALONIL or kresoxim-bromide in the presence of solubilizing agent. The technical result consists in the effective suppression of various fungi, especially in crops such as wheat. 2 N. and 11 C.p. f-crystals, 7 PL.

BACKGROUND OF INVENTION

The present invention relates to concentrated liquid fungicidal compositions containing fungicide acceptable carrier and

(a) at least one azole derivative of the formula I

in which

R1and R2each independently represents a hydrogen atom or optionally substituted alkyl, alkenylphenol, alkenylphenol or akadeemiline group;

R3represents a halogen atom or optionally substituted alkyl, alkenylphenol, alkenylphenol, akadeemiline, CNS or aryl group; and

the organisations, which exists in dissolved form; and

(b) one or more additional fungicide active ingredients that exist in the form of a suspension of small particles.

Fungicidal compounds of the formula I, which can be used in the present invention, is described in U.S. patent No. 4938792.

U.S. patent No. 5393770 discloses concentrated fungicidal compositions containing the compounds of formula I and solubilizing agents, and it is proposed to add various fungicide active ingredients, including dithianon, fenpropimorph and CHLOROTHALONIL, tank mixer with a compound of formula I for combating diseases caused by Erysiphe graminis f.sp. tritici.

So far not existed concentrated liquid compositions comprising a compound of formula I and the second fungicide active ingredient. Still upon receipt of compositions comprising a compound of formula I, solubilizers agent and the second fungicide active ingredient could not be obtained homogeneous or stable homogeneous composition due to the interaction between the second active ingredient and solubilization agent. However, the combination solubilizing substances of formula I with finely of diperkirakan zmoney fungicidal activity of the specified drug.

Unexpectedly it was found that the fungicidal composition which comprises a compound of formula I, the second fungicide active ingredient, a polar organic solvent, solubilizers agent and dispersing agent, which has the ability to irreversibly adsorb onto the surface of hydrophobic particles suspended in water or polar organic solvents, forms a stable suspension of particles of the second fungicidal active ingredient in the solution of the compounds of formula I in a liquid mixture of the other components. In addition, it was found that the physical state of the active ingredients is maintained even after these compositions are diluted with water, thus making it possible to create suitable for spraying solutions containing solubilizing compound of formula I and the fine particles of the second active ingredient.

Moreover, in previous works it is not intended that such compositions could be used successfully to suppress diseases of cereals such as Septoria spp.

BRIEF DESCRIPTION OF THE INVENTION

The present invention relates to concentrated liquid fungicidal compositions containing fungicide acceptable is soedineniya; which exists in dissolved form;

(b) one or more additional fungicide active ingredients that exist in the form of a suspension of fine particles;

(C) solubilizers agent; and

(d) dispersing agent that has the ability to irreversibly adsorb onto the surface of hydrophobic particles suspended in water or polar organic solvents.

Another aspect of the present invention is concentrated fungicidal composition containing fungicide acceptable carrier and/or surface-active agent and synergistically effective amount

(a) at least one azole derivative of the formula I, as defined above;

(b) CHLOROTHALONIL or kresoxim-methyl and

(c) solubilizing agent.

The present invention also includes a method of suppressing phytopathogenic fungi, which comprises applying a synergistically effective amount of at least one of the compounds of formula I and CHLOROTHALONIL or kresoxim-bromide in the presence of solubilizing agent.

A DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The composition of the ACC is about weight (weight/weight) of the active ingredients.

In the preferred embodiment of the present invention the liquid composition of the present invention includes

from 0.5 to 10%, preferably from 1 to 7%, by weight of the azole derivative of the formula I;

- from 15 to 60%, preferably from 20 to 40% by weight of at least one of the second fungicide active ingredient;

from 10 to 50%, preferably from 15 to 35%, by weight solubilizing agent;

from 0.1 to 5%, preferably from 0.2 to 2% by weight of one or more dispersing agent, one of which has the ability to irreversibly adsorb onto the surface of hydrophobic particles suspended in water or polar organic solvents;

from 0.1 to 5%, preferably from 0.5 to 2.5% by weight of the agent to prevent foaming;

from 5 to 30%, preferably from 7.5 to 25% by weight mixed with water or partially miscible with water and organic solvent;

from 0.01 to 0.5% by weight of a preservative;

from 0.05 to 1%, in particular from 0.1 to 0.6% by weight of a structuring agent; and

- optional, from 5 to 40%, in particular from 10 to 35% by weight water;

and the sum of all ingredients of the composition is 100%.

Before the R1and R2represents a C1-6alkyl group, preferably methyl group; and

R3attached in the para-position and represents a fluorine atom or a chlorine or C1-6halogenating group.

A particularly preferred compound for use in the present invention is metconazole having the formula IA

which is described in The Pesticide Manual, 11th Edition, The British Crop Protection Council and The Royal Society of Chemistry, 1997 (below referred to as "the Pesticide Manual"), page 803.

The compound of formula I, due to the basic nature of the azole ring, capable of forming salts or addition products with inorganic or organic acids or with metal ions. Examples of inorganic acids which form salts, are hydrogen halides), such as hydrofluoric acid, hydrochloric acid, Hydrobromic acid and uudistoodetena acid, and also sulfuric acid, phosphoric acid and nitric acid. Suitable organic acids include formic acid and alcamovia acid, such as acetic acid, triperoxonane acid, trichloroacetic acid and propionic acid, and, in togata, oxalic acid, alkylsulfonate acid, arylsulfonic acid, alkylphosphonate acid, arylphosphonate acid in which the alkyl and aryl fragments optionally substituted, as, for example, para-toluensulfonate acid, salicylic acid, para-phenoxybenzoic acid, 2-acetoxybenzoic acid or etc.

Metal ions, which are weak Lewis acid suitable for the formation of products of accession, are preferably ions of chromium, manganese, iron, cobalt, Nickel, copper, zinc, calcium, magnesium, aluminum, tin and lead.

However, the active ingredients of the formula I and a second fungicidal active ingredient is preferably used as such.

Second fungicidal compound is, as a rule, water-immiscible organic, in particular aromatic, solid compound, which has a melting point of at least 60°C, preferably between 70 and 280°C.

Second fungicidal compound can be, for example, so that it has the ability to fight diseases of cereals (e.g. wheat and barley), such as those that cause Erysiphe, Puccinia, Septoria, Gibberella, Rhynchosporium and Helminthosporium spp., braakenburg crops and vegetables, with powdery mildew and scab on apples and brassica disease, etc., These mixtures of fungicides provide a broader spectrum of activity than the compounds of General formula I separately.

Other examples of fungicidal compounds which may be used in the compositions of the present invention are anilazine, AZOXYSTROBIN, benalaxyl, benomyl, binapacryl, bitertanol, blasticidin S, Bordeaux mixture, bromuconazole, bupirimate, captafol, Captan, carbendazim, carboxin, cropropamide, chlorbenzene, CHLOROTHALONIL, chlozolinate, copper compounds such as copper oxychloride and copper sulfate, cycloheximide, having cymoxanil, lipoferum, tsyprokonazolu, cyprodinil, dichlofluanid, Dylan, dichloran, diclobutrazol, declomycin, dietphenterm, difenoconazol, dimethirimol, dimethomorph, diniconazole, dinocap, datalists, dithianon, dodemont, valleys, edifenphos, epoxiconazol, itaconate, ethirimol, etridiazole, famoxadone, verapamil, fenarimol, fenbuconazole, fanforum, fenpiclonil, fenpropidin, fenpropimorph, fentin, acetate fentin, hydroxide fentin, verison, fluazinam, fludyoksonil flamethower, Fluconazol, flusilazol, glucolipid, flutolanil, flutriafol, folpet, postillonne, fuberidazole, formazin, kitazin P, kresoximmethyl, MANCOZEB, MANEB, mepanipyrim, mepronil, metalaxyl, mefenoxam, myclobutanil, paasonen, Nickel dimethyldithiocarbamate, nitratenitrogen, nuarimol, operas, organic mercury compounds, oxadixyl, oxycarboxin, penconazole, pencycuron, finaince, phtalic, polyoxin D, polishers, provenzal, prochloraz, procymidone, propamocarb, propiconazol, propineb, pyrazophos, pirivenas, Pyrimethanil, pyroxylin, proxyfor, chinomethionat, jenoxifen, hintzen, spiroxamine, SSF-126, SSF-129, streptomycin, sulfur, tebuconazole, telital, tecnazene, tetraconazole, thiabendazol, leflunomid, thiophenemethyl, thiram, cyclophosphates, tolylfluanid, triadimefon, triadimenol, triazolyl, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin And, vinclozolin, XRD-563, Suriname, zineb, Zir, especially CHLOROTHALONIL and kresoximmethyl.

CHLOROTHALONIL is the General name of 2,4,5,6-tetrachloro-1,3-benzodiazepinee formula

which is described in "The Pesticide Manual", page 227.

Kresoximmethyl is the common name methyl(E)-2-methoxyimino-[2-(tolylacetic)phenyl]acetate formula

which is described in "The Pesticide Manual", p, the E. demonstrate synergistic effects.

Was unexpectedly discovered a strong synergy between the azoles of the formula I and CHLOROTHALONIL in experiments in the greenhouse, when these compounds are mixed and when compared the activity of this composition with commercial activity metconazole drug CARAMBA® 60 g/l SL and commercial activity CHLOROTHALONIL drug DACONIL® 500 g/l SC. In addition, it was found a strong synergism between the azoles of the formula I, kresoxim-stands in the presence of solubilizing agent in the experiments in the greenhouse, when these compounds were mixed in the tank and when the activity of this drug was compared with a commercial activity metconazole composition CARAMBA® 60 g/l SL and commercial activity kresoximmethyl composition 500 g/kg WG. Individual compounds and compositions used in the experiments for the treatment of powdery mildew of wheat and shielding experiments on suppression of diseases of wheat, in particular, Septoria spp. All application were conducted per hectare using a track sprayer so as to reproduce the actual conditions.

A mixture of fungicides demonstrates a synergistic effect if the fungicidal activity of the mixture is greater than the sum of the activities from the P CLASS="ptx2">If the actual efficiency (E) exceeds the expected (calculated) efficiency (EE), the mixture shows a synergistic effect.

Compositions of the present invention include compounds of formula I and CHLOROTHALONIL used together, in synergistically effective amounts. When used in this way, they demonstrate exceptional effectiveness against a broad spectrum of phytopathogenic fungi, in particular against fungi belonging to the classes of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. They are systemic and can be used as fungicides leaves and soil or seed treatment.

The mixture in accordance with the invention can preferably be applied to suppress the following phytopathogenic species of fungi belonging to the genera: Alternaria, Ascochyta, Botrytis, Cercospora, Colletotrichum, Erysiphy (Blumeria), Elsinoe, Fusarium, Gibberella, Guignardia, Helminthsporlium, Hemileia, Monilinia, Mycosphaerella, Agent, Pythium, Phytophthora, Plasmopara, Podosphaera, Pseudocercosporella, Pseudoperonospora, Puccinia, Pyraenophora, Pyricularia, Rhizoctonia, Rhynchosporium, Sclerotinia, Sclerotium, Septoria, Sphaerotheca, Tilletia, Typhula, Uncinula, Urcomyces, Ustilago, Venturia, Verticllium and other Mixture in accordance with the present invention is particularly suitable for suppression of Septoria nodorum, Blumeria graminis f.sp. tritici, Blumeria graminis f.sp. , Puccinia , Rhynchosporium secalis, Helminthosporium gramineum, Mycosphaerella pinodes, Botrytis c is located in the range from 1 to 500 grams of active ingredient per hectare (g and.and./ha), moreover, the volume of from 15 to 200 g and.and./ha often allow you to reach a satisfactory suppression. The optimal dose for a particular application depends on a cultivated culture and the predominant species of parasitic fungi and can easily be determined with the help of recognized biological tests, known to specialists in this field.

In General, the preferred dose of applying the second fungicidal active ingredient in accordance with this invention, in particular CHLOROTHALONIL or kresoxim-methyl, is in the range from 20 to 5000 g and.and./ha, preferably from 50 to 1500 g and.and./ha.

The optimal dose of the second fungicidal compounds, in particular CHLOROTHALONIL, depends, however, on a cultivated crop and the level of invasion by fungi and can be easily determined with the help of recognized biological tests.

The ratio (by weight) between the compound of formula I and a second antifungal compound, for example, between metconazole and CHLOROTHALONIL or kresoxim-stands, as a rule, is in the range from 1:200 to 2:1. The preferred ratio metconazole:CHLOROTHALONIL or metconazole:kresoxim-methyl may vary, for example from about 1:100 to about 1:1, ( approximately from 0.5 to 10% by weight of compounds of formula I and 15-60% by weight of the second fungicide active connection.

The active compounds are mixed together in a suitable ratio in accordance with the present invention, together with conventional carriers. Fungicide acceptable carriers are liquid media, preferably miscible with water, or partially miscible with water, organic solvents, or their mixtures with water. The preferred mixture are miscible with water, solvents and water. In the preferred embodiment of the present invention the weight ratio of mixing with the water solvent to water is in the range from 1:5 to 5:1, preferably from 1:2 to 2:1, in particular from 1:1.25 to 1.25 times:1.

Miscible with water or partially miscible with water and organic solvents used in the present invention may be alcohols and glycols and their ethers and esters, e.g. ethanol, propanol, butanol, pentanol, benzyl alcohol, ethylene glycol, propylene glycol, ketones such as methyl ethyl ketone or cyclohexanone, strongly polar solvents, preferably N-alkylpyridine, such as N-methyl-2-pyrrolidone, N-n-octyl-2-pyrrolidone or N-cyclohexyl-2-pyrrolidone, or lactones, such as-butyrolactone and, in particular, propylene glycol. Also suitable with ptx2">Solubilization agent used in the present invention, preferably the surface-active substance, namely alkoxylated aliphatic alcohols. Preferred alkoxylated aliphatic alcohol-based CNS plot with 2 carbon atoms, thus represents ethoxylate, or with 2 or 3 carbon atoms, thus is a mixture of ethoxylates/propoxylate. In the preferred aliphatic alcohol alkoxylate CNS circuit can have at least 5 CNS sections, suitably from 5 to 25 CNS areas, preferably from 5 to 15, and more preferably from 5 to 9. Alcohol area, as a rule, is derived FROM9-18aliphatic alcohol. Preferred alcohols are at least 50% by weight of the primary and at least 50% by weight remotemachine alcohols and at least 50% by weight have a single hydroxyl group. The number solubilizing agent is typically about 10-50% by weight of the composition.

In particular, the preferred solubilizers agents are such agents as alcohol ethoxylates NEODOL® (last DOBANOL®) supplied by Shell Chemical Co. Ltd. In preferably the I lies in the range from 5:1 to 20:1, preferably from 5:1 to 15:1.

Dispersing agent that has the ability to irreversibly adsorb onto the surface of hydrophobic particles suspended in water or polar organic solvents, preferably selected from the group of polymeric surfactants, preferably surface-active acrylic graft copolymers (such as those sold under the trade name ATLOX®) or from the group of polymeric naphthalenesulfonate. Additional dispersing agents that can be used in accordance with the present invention, are commercially available salts of esters of polyarilensulphone, especially its sodium, potassium and ammonium salts; and the preferred salts are potassium salts sold under the trademark SOPROPHOR®.

In the preferred embodiment of the present invention the weight ratio between the dispersing agent and additional fungicidal active ingredient is in the range from 1:50 to 1:300, preferably from 1:100 to 1:150. In typical cases, the dispersing agent is present in amount of from about 0.1 to 5% of the composition by weight.

The preferred organic solvent, azole derivative of the formula I, in particular metconazole;

at least one second fungicide active ingredient; in particular CHLOROTHALONIL or kresoximmethyl;

- solubilizers agent, such as alkoxylated aliphatic alcohol, which is an ethoxylate or a mixture of ethoxylates/propoxylate consisting of from 5 to 25 CNS areas, in particular alcohol NEODOL ethoxylates® (commercially available from Shell Chemical Co. Ltd.); and

- one or more dispersing agents, which have the ability to irreversibly adsorb onto the surface of hydrophobic particles suspended in water or polar organic solvents, preferably selected from the group of surface-active acrylic graft copolymers, such as ATLOX® 4913 (commercially available from ICI Surfactants), and polymer naphthalenesulfonates, such as SUPRAGIL® MNS 90 (commercially available from Rhodia, formerly Rhone-Poulenc);

agent for preventing foaming, in particular a mixture of perforaciones acid and/or performancereview acid, in particular Defoamer® SF or Fluowett® PL 80 (commercially available from Clariant GmbH); and

- optional water.

In the preferred vopl in the composition, less than 3.0 mm, preferably from 1.3 to 2.7 μm, especially from 1.5 to 2.5 μm. In typical cases, this amount is achieved using a conventional crushing plant.

Compositions of the present invention are stable suspension of particles of the second fungicide active ingredient, in particular CHLOROTHALONIL, in a solution of the compounds of formula I, in particular metconazole, in the liquid mixture of the other ingredients. Deposition in the compositions accordingly the present invention when stored under normal conditions is acceptable. The physical state of the active ingredients persists after cultivation of these compositions with water, i.e., the obtained solutions for spraying containing the solubilized metconazole and small particles CHLOROTHALONIL without violating separation of phases. The combination solubilizing of metconazole and finely dispersed particles of CHLOROTHALONIL is essential in order to achieve the highest possible fungicidal activity of the specified drug.

Also provided is a method of obtaining such compositions, which comprises bringing a compound of the formula I and additional fungicidal active ingredient, in particular CHLOROTHALONIL, as the definition is or mixtures of isomers may have different levels or spectra of activity and thus, the composition can include individual isomers or mixture of isomers.

A carrier composition in accordance with the invention is any liquid substance, with which is combined an active ingredient, to facilitate application to the treated area, which may be, for example, plants, seeds or soil, or to facilitate storage, transport or use. The composition can be in the form of liquid concentrates using traditional techniques. These methods include intensive mixing and/or grinding the active ingredients with other substances, such as solvents, surface-active substances (surfactants), and optionally solid and/or liquid excipients and/or adjuvants. The method of application, such as spraying, atomization, dispersion or pouring, can be selected as a composition in accordance with achievable goals and these terms and conditions.

The pesticide compositions are often manufactured and transported in a concentrated form, which is then diluted by the user before use. The presence of a small number of media, which is a surfactant that facilitates razvedenia invention was surfactants. For example, the composition may contain two or more media, and at least one of them is a surfactant. Surfactant can be nonionic, anionic, cationic or zwitterionic substance with good dispersing, emulsifying and wetting properties, depending on the nature of the compounds corresponding to General formula I, which is included in the composition. Surfactants can also be a mixture of individual surfactants.

Compositions of the invention may also contain other additives, such as agents that prevent foaming, preservatives, corrosion inhibitors, stabilizers, structuring agents, agents promoting penetration, adhesives and water or an organic liquid in which the active ingredient is essentially insoluble; in the composition may be some organic solids or inorganic salts in dissolved form to prevent sedimentation and crystallization or as agents for preventing the freezing of water. Suitable preservatives include antimicrobial 1,2-benzisothiazolin-3-one sodium, sold under the trademark Proxel®. Suitable structuring agents are clays such as glecting ingredient may also be increased using the inclusion of the adjuvant solution for spraying. Adjuvant is defined here as a substance that may enhance the biological activity of the active ingredient, but it does not possess significant biological activity. Adjuvant may either be included in the composition as an integral part or the media, or may be added to the tank for spraying with a composition containing the active ingredient.

As a consumer product composition preferably may be in a concentrated form, while the user usually uses a diluted composition. The composition can be diluted to a concentration of active ingredient 0.001%. Usual doses are in the range of from 0.01 to 10 kg.to./ha.

Examples of compositions in accordance with the invention are:

Composition And receive, dissolving metconazole in propylene glycol and Neodol 91-6 (pre-mixture (I) by mixing together the remaining ingredients using a high-speed mixer (pre-mixture (II) and mixing together the preliminary mixture I and the preliminary mixture II.

The song get In, dissolving metconazole in propylene glycol and Neodol 91-6 (pre-mixture (I) mixing together the rest of ingredkents to an average particle size of 1.5 to 2.5 μm (pre-mixture (II) and mixing together the preliminary mixture I and the preliminary mixture II.

Composition To receive in accordance with the same technique as composition A.

The ingredients of the compositions a, b and C are available from the following sources:

1)available from ICI Surfactants

2)available from Shell Chemical Co., Ltd.

3)available from Rhodia

4)available from Clariant GmbH

5)available from Zeneca

6)available from Engelhard Corp.

The separation of compositions a and b were tested as follows.

The composition was stored for 8 weeks at different temperatures or temperature cycle between 0 and 35°C (0/35), respectively. The volume of liquid supernatant (W.with.) evaluated visually and expressed in volume percent. The precipitate (sieges.) assessed through careful introduction of glass sticks to the vessel and found that it is negligible (NESN.) or present only in trace quantities (SL.). The results of this experiment are shown in table I.

As a consumer product composition in accordance with the present invention are provided in a concentrated form, while the end user usually uses a diluted composition. The composition may be diluted to conticini crop yields, infected by diseases caused by fungi, preferably Ascomycete fungi, in particular Blumeria graminis, Botrytis cinerea and Micosphaerella or Basidiomycote fungi, in particular Puccinia hordei and Uromyces pisi, which includes the protection of crops from diseases caused by these fungi, or handling infected plants or the environment in which they are grown an effective amount of diluted fungicide composition in accordance with the invention, in particular comprising metconazole and CHLOROTHALONIL or kresoxim-methyl in combination with solubilizers agent.

In the preferred embodiment of the barley harvest, which protect against powdery mildew and/or rust, and protein yields of peas, which protects against spots on leaves, grey mildew and/or rust, can be increased by using the method of the present invention.

The following examples illustrate specific embodiments of the present invention; however, the invention is not limited to the illustrated thus the embodiments, but includes the whole scope of the claims attached formula.

EXAMPLES

Action CARAMBA® (60 g/l of metconazole), DACONIL® (500 g/l CHLOROTHALONIL) and metconazole/CHLOROTHALONIL 30/375 g/l SC mixed compositions (Kosirnik font) CARAMBA and DACONIL in different doses were evaluated in comparison with the shares of metconazole/CHLOROTHALONIL composition (Composition C) against wheat Septoria nodorum in 3-day residual test (pollinate with a sprayer on tracks with sprinkler nozzle uniform spraying for 3 days before infection by a pathogen).

The calculation was performed by assessing the percentage of infected leaf surface at each of the 4 repetitions. The activity in % is calculated using ABBOTT's formula:

% activity = 100% infection treated/% infection untreated × 100

The results are shown in table II, in which the experimentally obtained efficiency in bold, and the expected value is given in brackets in italics.

From these results it is clear that both products one were inactive against wheat Septoria nodorum in the tested quantities, while the effectiveness of the composition was 29-71% of control in the tested doses, which suggests a strong synergism.

Example 2

Efficiency (% from control, in bold) CARAMBA and DACONIL in different doses were evaluated in comparison with the shares of metconazole/CHLOROTHALONIL 30/375 g/l SC composition (Composition C) against powdery mildew of wheat in a 2-day medical test (pollinate with a track sprayer with sprinkler nozzle uniform spray 2 days after infection cereal pathogen).

The results are shown in table III, in which italics.

CHLOROTHALONIL was inactive against powdery mildew of wheat, and a higher dose of metconazole, for example 5.6 g and.and./ha, was less active than the lower dose of metconazole (3.8 g and.and./ha) in combination with CHLOROTHALONIL (47 g and.and./ha) - this combination had an efficiency of 95% from the control of the disease, whereas the expected effectiveness of higher doses of the composition would be less than 70% control. These results clearly show the synergistic combinations.

Example 3

Leaf spot and grey mould in protein peas Lingot® is commercially available WG composition comprising 50% by weight of CHLOROTHALONIL and 16.7% by weight of vinclozolin and is a commercial standard fungicide for protein peas. Caramba® is commercially available SL composition comprising 6% by weight of metconazole. Protein peas were grown in the field. The processing of active ingredients (Lingot®, Caramba® and metconazole/CHLOROTHALONIL 30/375 g/l SC (Composition C) or untreated control) was performed in accordance with a rich agronomic practices. Infection of leaf spots and gray mold was determined by assessing the infected area of the worksheet. The composition of this invention was demonstrated . the received yield and increased yield compared with the untreated control in these field tests shown in table IV.

Example 4

Powdery mildew and rust in barley Punch® is commercially available SE composition comprising 25% by weight of flusilazole and 12.5% by weight carbendazin and is a commercial standard fungicide for barley. Barley was grown in the field. The processing of active ingredients (Punch® and metconazole/CHLOROTHALONIL 30/375 g/l SC (Composition C) or untreated control) was performed in accordance with a rich agronomic practices. Infection of powdery mildew and rust was determined by assessing the infected area of the worksheet. When the pressure powdery mildew low to medium composition of the present invention suppresses the disease equally in comparison with Punch®. At moderate pressure of the rust composition of the present invention suppresses the disease in the superlative degree of comparison with Punch®. Barley was collected. Yield and increased yield compared with the untreated control in these field tests shown in table V.

Example 5

Fu;, 6-day residual test

The tank mixes were obtained from commercially available Caramba® and dispersible in water granulated compositions containing 500 g kresoxim-bromide per kg

The active ingredients in different doses, the observed and expected when this efficiency is given in table VI.

Example 6

Fungicidal efficacy of the mixture metconazole/kresoxim-methyl against Blumeria graminis, wheat, variety 'Kanzler' 15-day residual test

The tank mixes were obtained from commercially available Caramba® and dispersible in water granulated compositions containing 500 g kresoxim-bromide per kg of Active ingredients in different doses, the observed and expected when this efficiency is given in table VII.

1. Concentrated liquid fungicidal composition comprising fungicide-acceptable carrier and

(a) at least one compound of formula IA

or one of its salts or products of accession, which exist in a soluble form; (b) one additional fungicide active ingredient which is not miscible with water and has a melting point of at least orbiculata on the surface of hydrophobic particles, suspended in water or in polar organic solvents, and optionally other additives selected from the group comprising agents that prevent foaming, preservatives, corrosion inhibitors, stabilizers, strukturiruya agents, agents promoting penetration, sticky substance and carrier liquid with water or an organic liquid in which the active ingredient is essentially not soluble in synergistic effective amounts.

2. The composition according to p. 1, wherein the carrier liquid comprises mixing with the water or partially miscible with water, an organic solvent or its mixture with water.

3. Composition under item 1 or 2, characterized in that the compound of formula I is metconazole.

4. Composition according to any one of the preceding paragraphs, characterized in that the ratio (by weight) the azole derivative of the formula I (a) additional fungicidal active ingredient (b) is 12,5:1 - 1:1.

5. The composition according to p. 2, characterized in that the particle size of said additional fungicidal active ingredient is less than 3.0 mm.

6. The composition according to p. 5, characterized in that the particle size mentioned additionally, the additional fungicidal active ingredient is CHLOROTHALONIL or kresoxim-stands.

8. Composition according to any one of the preceding paragraphs, which includes as a carrier 5 to 30% by weight miscible with water or partially miscible with water, an organic solvent, and, optionally, 5 to 40% by weight of water.

9. Composition according to any one of the preceding paragraphs, characterized in that the dispersing agent is a surfactant acrylic graft copolymer enable or polymer naphthalenesulfonate.

10. Composition according to any one of the preceding paragraphs that includes an agent that prevents foaming.

11. The composition according to p. 10, wherein the agent for preventing foaming, is a mixture of perforaciones acids and/or performancereview acids.

12. Composition according to any one of the preceding paragraphs, which comprises 0.5 to 10% by weight of compounds of formula I; 15 to 60% by weight of at least one of the second fungicide active ingredient; 10 - 50% by weight solubilizing agent; 0.1 to 5% by weight of one or more dispersing agents, one of which has the ability to irreversibly adsorbiroval what about the weight of the agent, prevent foaming; 5 to 30% by weight miscible with water or partially miscible with water and organic solvent; from 0.01 to 0.5% by weight of a preservative; 0.05 to 1% by weight of a structuring agent; and, optionally, 5 to 40% water.

13. A method of inhibiting the growth of fungus in the lesion, which includes the dilution of a concentrated composition according to any one of the preceding paragraphs of water and applying the diluted mentioned composition to the lesion.



 

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where R is hydrogen, C1-C3alkyl group, unsubstituted or substituted by one or more halogen atoms, allyl group; X is hydrogen, halogen, C1-C3alkyl group, a C2-C3alkylamino group, unsubstituted or substituted by one or more halogen atoms, C1-C3CNS group, C1-C3alkoxymethyl group

The invention relates to new fungicidal compositions intended for the treatment of phytopathogenic diseases of cultivated plants, in particular of diseases caused by phytopathogenic fungi, and to a method of combating phytopathogenic diseases of cultivated plants

The invention relates to okimawin esters of the formula I or its possible isomers or mixtures of isomers, where X denotes a nitrogen atom, and Y designates O or NH, or X represents CH, a Y denotes Oh, and where further R1represents C1-C4alkyl; R2represents C1-C4alkyl, cyclopropyl, cyano; R3represents C1-C6alkoxycarbonyl, unsubstituted or substituted phenyl, cyano, methoxy group or atenilol, di (C1-C6alkyl)-aminocarbonyl, C1-C6alkyl-S(O)n, aryl-S(O)n, unsubstituted or substituted C1-C6by alkyl; R4means C1-C6alkyl, C1-C6haloalkyl 1-5 halogen atoms; C1-C4alkoxy-C1-C2alkyl; C3-C6quinil; C3-C6-cycloalkyl-C1-C4alkyl, unsubstituted or substituted by 1-4 halogen atoms; n = 1 or 2

The invention relates to the field of pest control, in particular fungicidal tool and method of combating fungi
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