SK130793A3 - Fungicidal 2-alkoxy-2-imidazoline-5-on derivatives - Google Patents

Abstract

2-Alkoxy-2-imidazolin-5-one derivatives of general formula (I): <IMAGE> in which: R<1> denotes an aryl radical, R<2> denotes an alkyl or haloalkyl radical, R<3> denotes an alkyl or haloalkyl group, R<4> denotes an aryl radical, R<5> denotes H or a formyl, acyl, aroyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphonyl or arylsulphonyl radical. The invention also relates to the preparation of these compounds and to their use as broad-spectrum fungicides.

Description

The invention relates to novel 2-alkoxy-2-imidazolin-5-one compounds which are useful for plant protection. The invention also relates to a process for the preparation of said compounds and products, which may optionally serve as intermediates in these processes. The invention further relates to the use of said compounds as fungicides, fungicidal compositions based on these compounds, and to a method of combating fungal crops diseases using said compounds.

It is an object of the present invention to provide compounds which exhibit improved properties in combating fungal plant diseases.

Another object of the invention is to provide compounds which have an improved application spectrum in the field of fungal plant diseases.

Summary of the Invention wherein these objectives can be achieved in whole or in part thanks to the products of the invention which are 2-and 1-alkoxy-2-imidazolin-2-one derivatives of the general formula I

in which

R 'represents an aryl group selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl and methylenedioxyphenyl, each of which is optionally substituted up to 3; groups selected from the group consisting of R ^s ,

R @ 1 represents an alkyl group or a haloalkyl group containing 1 to 3 carbon atoms, wherein

In addition, R ¹ and R ² together with the carbon atom to which they are attached may form a carbocyclic or heterocyclic group containing 5 to 7 atoms, which cyclic groups may be fused to a phenyl group and each of which may be optionally substituted i to 3 groups selected from the group consisting of meanings

R ³ represents an alkyl or haloalkyl group containing 1 to 3 carbon atoms,

R ^u is an aryl radical from the group consisting of phenyl, naphthyl, pyridyl, pyrimidyl fishing, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, b as well línylovú, i Žoch ino l íny1ovú group, a methylenedioxyphenyl, wherein each of which is optionally substituted with 1 to 3 radicals from the group consisting of R ^a,

R ^p is H, formyl, acyl of 2 to 6 carbon atoms, an aroyl group, an alkoxycarbonyl group having 2 to 6 carbon atoms, aryloxycarbonyl, alkylsulfonyl or aryl sulfonyl 1 s 1 s 1 U is,

R ⁶ is

a halogen atom, or

an alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, and haloalkyloxy, haloalkythio, cyanoalkyl or alkylsulfonyl group having from 1 to 6 carbon atoms.

- cycloalkyl, halo cycloalkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio or a 1 to iynylthio group containing 3 to 6 carbon atoms, or

a nitro group or a cyano group or a thiocyanato group, or

- an amino group which is optionally mono- or disubstituted by an alkyl or acyl group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 2 to 6 carbon atoms,

a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfonyl group or a pyridyloxy group, these groups being optionally substituted by one or more substituents selected from the group consisting of.

- halogen atom,

- an alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl group containing 1 to 6 carbon atoms,

- cycloalkyl, halo-cyclic, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, and from 1 to 6 carbon atoms,

a nitro group. cyano or thiocyanato,

- an amino group which is optionally mono- or disubstituted by an alkyl or acyl group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 2 to 6 carbon atoms, and

a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfonyl group or a pyridyloxy group, and their i Tam i.

Preferred compounds of the invention are compounds of formula II (ΣΙ)

wherein R 1 and R ⁶ have the meanings given above.

Even more preferred compounds of the invention are those wherein R ^d is phenyl, substituted phenyl, pyridyl or substituted pyridyl and R ⁵ is hydrogen or acyl (e.g., acetyl).

Compounds of formula (I) are obtained by reacting a 2aalkyl-10-imidazolin-5-one of formula (III) with an alcohol of formula (R ⁾ OH in the presence of a strong base according to the following reaction scheme:

S — R ' ³ γ — R' i

R ^:

R ³ OH principle

solvent

wherein R ¹ , R ² , R ² and R "have the meanings given in connection with the general formula I and R ' ³ represents an alkyl group having 1 to 3 carbon atoms.

As a strong base may be used an alkali metal alkoxide of formula R ³ 0 ^- M +, an alkali metal or strong organic base. This reaction is preferably carried out in an alcohol R ³ OH as a solvent, using the corresponding sodium alkoxide R ³ M a * as the base. The reaction is carried out at a temperature of 20 to 80 ° C. The 2-alkylthio-2-imidazolin-5ones of formula III are obtained by any of the methods described in European patent application EP 0 551 048. Acylation of compounds of formula I in which R ⁵ is hydrogen is carried out by conventional methods.

Salts of compounds of formula I can be prepared by known methods.

In the following, the invention will be explained in more detail by way of examples of specific embodiments thereof, these examples being for the purpose of illustration only and are not intended to limit the scope of the invention, which is clearly defined by the wording of the claims. These examples illustrate the compounds of the invention, processes for their preparation and their antifungal properties. The chemical structures of the prepared compounds were verified by at least one of the following spectral analyzes: Ή-Nuclear Magnetic Resonance Spectroscopy, ¹³ C-Nuclear Magnetic Resonance Spectroscopy, Infrared Spectroscopy and Mass Spectroscopy. In the table below, the following abbreviations are used for methyl, ethyl, propyl, pyridyl, acetyl and phenyl: Me, Et, Pr, Py, Ac and Ph.

DETAILED DESCRIPTION OF THE INVENTION

Example 1

Preparation of compound no. Second

In a three-necked flask containing 100 ml of dried nitrogen, 1.4 g in 60 ml of ethanol were reacted. To the reaction mixture, 4 g (1.28% v / v) are then added under a sodium atmosphere (1.74 mmol).

6 mmol) of 4-methyl-2-methylthio-4-phenyl-1-phenylamino-2-imidazolin-5-one. The reaction mixture was then heated at reflux for 6 hours. The mixture was cooled to ambient temperature and acidified with 0.4 mL of acetic acid, then diluted with 300 mL of ethyl acetate. The organic solution is washed with water, then dried over magnesium sulphate and concentrated under reduced pressure to give a brown-red honey-like consistency. The product is purified by chromatography on a silica gel column. 1.25 g (yield 31%) of Compound (2) is obtained as a pinkish powder, m.p. 106 ° C.

The following compounds are prepared in the same manner:

table

no. R6 R3 R4 R 5 M.p. (° C) 1 - Me ph H 149 2-- ..... '...... ·. et ph H 106 3 - nPr ph H 80 .1 T 4-Cl Me ph H 140 5 - Me _: 2-Me-Ph H 118 6 4-Cl Me 2-pyridyl H ' 150 8 ' - Me 2-Cl-Ph H 94 9 - Me 4-Cl-Ph H 124 ll; 3,4-di (MeO) Me ph H 150 12 4-Cl Me 4-Cl-Ph H 176 13 4-Cl Me 4-F-Ph H 147 14 4-Cl Me. 2-Cl-Ph H honey konzist. 15 4-Cl Me 3-Cl-Ph H 147 16 4-Cl Me 4-Me-Ph H 162 17 4-Cl Me 3-Me-Ph H 116 18 4-Me Me ph H 110 19 4-F Me ph H 104

Tables (continued)

20 4-Cl Me 2-Me-Ph H honey konzist. 21 4-F Me 3-Me-Ph H 1 14 23 4-F Me 2-Me-Ph H 88 24 4-Me Me 4-Cl-Ph The Loo 25 4-Me Me 3-Cl-Ph H 155 27 4-Me Me 2-Cl-Ph U L 4 86 28 4-Me Me 4-F-Ph The 124 29. 4-F Me 3-Cl-Ph The 160 30 4-Me Me 4-Me-? H H 155 31 4-F Me 4-Me-Ph H 149 32 ' 4-Me Me 2-Me-Ph K. 128 JJ - Me 3-F-Ph The 121 34 4-Me Me 3-Me-Ph H 138 35 4-Ph Me 2-Me-Ph The 120 36 4-F Me 4-Cl-Ph H 142 37 - Me. 4-F-Ph ri 157 38 - Me 2,4-di (F) -Ph H 166 39 - Me 4-Me-Ph H 116 40 4-F Me 2-F-Ph The honey konzist. 41 4-Me Me 2-F-Ph H 90 42 4-C1 Me 2-F-Ph H iredová konzist.

Ta bal ka (continued)

43 4-F. Me 2-Cl-Ph H 'speech konzist. 1 f T T - Me 2,3-di (Me) -Ph H 140 45 - Me 3-Cl-2-pyridyl H 140 46 - Me 3-Me-Ph H 54 47 - Me 2-F-Ph H 136 48 - Me 3-Cl-Ph H 93 49 4-F Me 3-Me-2-pyridyl H 126 50 4-F Me 3-F-Ph H 120 5 i 4-Cl Me 3-F-Ph H 125 52 3-Cl Me ph H 155 53 3-Cl Me 3-Me-Ph The 100 54 3-Cl Me 3-Cl-Ph H 105 55 3-Cl Me 3-F-Ph The 135 56th 3-Cl Me 2-Me-Ph H 116 57 3-F Me ph H 134 53 * r- J-R Me 3-F-Ph H 1 i5 59 Me ph Ac 121 60 3-F Me 3-Cl-Ph The 90 ó i 3-Me Me ph H 93 62 3-Me Me 3-F-Ph H 113 63 4-Ph Me 2-pyridyl H 146

Table (continued)

64 2.4 DIF Me ph H 163 65 2.4 DIF Me 3-F-Ph H 162 66 4-Ph Me ph H 114 6 ' 4-Ph Me 3-F-Ph H 56 68 2-C1 Me ph H 214 about? - Me 4-Ph-Ph H 118 70 2-C1 Me 3-F-Ph H 201 71 2-F Me ph H 172 2-F Me 3-F-Ph H 151 73 24-difluoro Me 3-Cl-Ph H 130 74 2-F Me 3-Cl-Ph H · 15i 75 ' 4-iPr Me ph H 132 76 4-Ph Me 3-Me-2-pyridyl H 142 77 4-iPr Me 3-F-Ph H 128 78 3-Me Me. 3-Cl-Ph H 115 79 4-iPr Me 3-Cl-Ph H 139 80 4-3r Me ph H 138 ARE YOU 4-NO2 Me ph H 143 82 3-Ph Me ph H honey konzist 85 2,4-di (F) -L-Ph Me 3-F-Ph. H 71 84 2,4-di (F) 4-Ph Me ph H 76

- 11 Table (continued)

S 5 4-F-4-pho M c ph H 91

Compound # 7:

T., t. = 71’C

2

Compound No. 8 ô:

MP: Mp = 98 ° C.

Example 2

In vivo test for Plasmopara viticola (peronospora)

An aqueous suspension of the active ingredient, the following composition is prepared using fine grinding, is tested:

- active substance: 60 mg,

- Tween 80 surfactant (oleate for polyoxyethylene sorbitan derivative) diluted with water to a concentration of 10%: 0, 3 ml,

- make up to 60 ml with water.

The aqueous suspension is then diluted with water to obtain the desired active concentration. 1 átky.

The cuttings of vine (V i t i s vinifera, Chardonay variety) are allowed to rise in pots. When the vine plants are two months old (8th to 10th leaf stage, 10 to 15 cm high), they are sprayed with the above suspension. Some other plants that serve as control plants in this test are sprayed with aqueous solutions that do not contain the active ingredient. After drying for 24 hours, each ingrowth is contaminated by spraying with an aqueous spore suspension of Plasmopara viticola,

3 at about 13 ° C for 5 days at a temperature of about 90-100% humidity obtained from a 4 to 5 day culture that was suspended to a final concentration of 100,000 units / cm ³ . The infested plants are then incubated for two days at a temperature saturated with humidity and then for 20-22 ° C in an atmosphere of relative humidity. Seven days after infestation of the plant comparisons, an evaluation of the condition of the plants versus the control plants is performed. Under these conditions, good (at least 75%) or total plant protection g / l of the following compounds: 1, 3 to 21, 23, to 83, 84 and 86.

is achieved at dose 1

25, 27-81,

Example 3

In vivo test of recondition (wheat rust)

By finely grinding, an aqueous suspension of the active substance to be tested is prepared with the following composition:

- Active substance: 60 mg

- Tween 80 surfactant (polyoxyethylene sorbitan oleate), diluted with water to a concentration of 10%: 0 · 3 m 1,

- make up to 60 ml with water.

The aqueous suspension is then diluted with water to obtain the desired concentration of active ingredient.

Wheat sown in pots filled with a mixture (50:50) of peat and pozzolan is sprayed at the height of 10 cm with the above aqueous suspension. After 24 hours, the wheat is sprayed with a spore suspension (100,000 spores / cm ³ ). This suspension was obtained from infested plants. The wheat is then enclosed for 24 hours in an incubation chamber at a temperature of approximately 20 ° C and a relative humidity of 100%. The wheat is then kept for 7-14 days at a relative humidity of 60%. Between 8 and 15 days after the infestation, a plant status assessment is made by comparison with untreated control plants. Under these conditions, good (at least 75%) or complete control is achieved at a dose of 1 g / l of the following compounds:

1, 4 to 10, 14, 15, 19 to 21, 23, 25, 27 to 29, 31 to 33, 35, 37, 39, 40 to 43, 50 to 55, 57, 58, 60, 61, 63 to 67, 69, 71 to 80, 82 to 84 and 86.

Example 4

In vivo test for Phytophthora. infestans

By finely grinding, an aqueous suspension of the active substance to be tested is prepared with the following composition:

- active substance: 60 mg,

- Tween 80 surfactant (oleate for 1-yoxyethylene sorbitan derivative), diluted with water to a concentration of 10%: 0,3 ml,

- make up to 60 ml with water.

The aqueous suspension is then diluted with water to obtain the desired concentration of active ingredient.

Tomato plants (Marmande variety) are grown in pots. When these plants are one month old (Stage 5-6 leaf, height 12-15 cm), they are sprayed with the above suspension with different concentrations of the compound to be tested. After 24 hours, each plant is infested by spraying an aqueous spore suspension (30,000 spores / cm ³ ) of Phytophthora infestans. After this infestation, the tomato plants are incubated for 7 days at approximately 20 ° C in an atmosphere saturated with humidity. Seven days after the infestation, the condition of the plants treated with the active substance is evaluated by comparison with the condition of the plants used as control subjects. Under these conditions, good (at least 75%) or complete plant protection is achieved at a dose of 1.g / l of the following compounds: 1, 4 to 10,

15, 18 to 21, 23, 28, 29, 31 to 33, 36, 37, 39, 42 to 44, 46, to 55, 57, 58, 60 to 67, 72 to 74, 81, 84 and 86.

5

Example 5

In vivo test for P i ricolari and oryzae (rice piriculariosis)

By finely grinding, an aqueous suspension of the active substance to be tested is prepared with the following composition:

- active substance: 60 mg,

- surfactant (polyoxyethylene sorbitan derivative oate), diluted with water to a concentration of 10%: 0,3 ml,

- make up to 60 ml with water.

The aqueous suspension is then diluted with water to obtain the desired concentration of active ingredient.

The rice, sown in condensers filled with a mixture (50:50) of enriched peat and pozzolan, is sprayed at the 10 cm height (corresponding to leaf stages 2-3) with the above aqueous suspension. After 24 hours, an aqueous spore suspension of Piricularia oryzae, obtained from a 15-day culture, is applied to the leaves of the rice plants, which is suspended to a concentration of 100,000 units / cm ³ . The rice plants are then incubated for 24 hours (25 ° C, 100% relative humidity), then placed under the same conditions in an observation chamber for 5 days. 6 days after the infestation, the plant condition is evaluated.

Under these conditions, reaches good (at least 7 5%) . or úp 1 - protection at dose 1 g / l of the following plants : 1, 4 to 7 17, 19, 20 23 _: , 25, 29 , 31 and 33, 35, U-0 and az 4 3, 46 47 , 5 0 52, 54, 5 5, 57. 5 N, 6 1, 53-67, 71, 72.74, 73, 32, 3i and 35 Example 6 Test in vivo on the Septoria tritici p š e n i ce)

By fine grinding, an aqueous suspension of the active substance to be tested, 1 g / l, is prepared with the following composition:

6

- effective dose: 60 mg,

- acetone: 5 m 1,

- surfactant (oleate for 1-yoxyethylene sorbitan derivative), diluted with water to a concentration of 10%: 0,3 ml,

- make up to 60 ml with water.

The aqueous suspension is then diluted with water to obtain the desired concentration of active ingredient.

Wheat plants (Oarius variety), sown in a mixture (50:50) of peat and pozzolan and grown in a greenhouse at 10 ° C, are sprayed at the first leaf stage (approximately 10 cm high) with the above active ingredient suspension. Some plants used as control subjects are sprayed with aqueous solutions that do not contain the active ingredient. 24 hours after this treatment, the plants are contaminated by spraying with an aqueous spore suspension (500,000 spores / ml) obtained from a 7-day culture. After infestation, the plants are placed in a humid atmosphere at a temperature of ’C. Evaluation of plant condition by comparison with account status, 9, i

52, 54, and 36.

rasti in is done 20 days after the infestation plants. For those- Enok the dos iahne good (at least 75%) or complete och - 11 í n at dose 1 3/1 following the compounds: 1, 4 until o n , u U, , 2 3 , 3, 2, 33, 35 to 37, 40, 42 to 45, 47, 48 50. δ 5, 57. 58, 60, 6 2 to 64, 66, 67, 7 1 to 80, 83. 84

The above results clearly demonstrate the good fungicidal properties of the compounds of the invention to fungal plant diseases caused by fungi belonging to a wide variety of families, including, for example, Phythomycetes, Basidiomycetes, Ascomycetes or Adungomycetes or Fungi Imperfecti, Wheatgrass, wheat and piricouriosis rice.

In practical applications, the compounds of the invention are rarely used alone. These compounds more often form part of fungicidal compositions. These compositions, which can be based on the above-mentioned properties of the active substances which

7 contain, to be used as fungicidal agents, they contain a compound of the invention as active ingredient in combination with solid or liquid vehicles meeting the requirements for their use in agriculture, and with agriculturally acceptable surfactants. In particular, inert and conventional vehicles and conventional surfactant are used in this regard. These compositions also form part of the invention.

The compositions may also contain any other additive such as a protective colloid, an adhesive, a compacting agent, a thixotropic agent, a penetrating agent, a stabilizing agent, a sequestering agent and the like. More usually, the compounds of the invention may be combined with all solid or liquid additives corresponding to conventional formulation techniques.

The compositions of the invention typically contain about 0.05 to 95% by weight of a compound of the invention (hereinafter referred to as the active ingredient), one or more solid or liquid carriers, and optionally one or more surfactants.

The term vehicle or carrier is used herein to mean any natural or synthetic, organic or inorganic material with which the active substance is combined for easy application to the plant, seeds and soil. This carrier is thus generally inert and must be agriculturally acceptable, especially for the plant to be treated. This carrier may be solid (clays, natural or synthetic silicates, silicas, resins, waxes, solid fertilizers and the like) or liquid (water, alcohols, especially butanol, and the like).

The surfactant may be an emulsifying, dispersing or wetting agent of the ionic or non-ionic type. Examples of surfactants which may be mentioned are the salts of polyacrylic acids, salts of ignosic acids, salts of phenolsulfonic or naphthalenesulfonic acids,

3 polycondensates of ethylene oxide with fatty alcohols or fatty acids nec or with fatty amines, substituted phenols (especially alkylphenols or aryl phenylphenols), salts of sulfosuccinic acid esters, taurine derivatives (especially and 1 cytaurates), phosphoric acid esters and polyoxyethylene. phenols or alcohols, fatty acid esters and polyols, and derivatives of the aforementioned compounds containing sulfate, sulfonate and phosphate functional groups. when the active compound and / or the inert carrier is resp. are water insoluble and that the carrier environment is water, the composition must contain at least one surfactant.

The compositions according to the invention intended for agricultural use can thus contain the active compounds according to the invention in a wide concentration range from 0.05 to 95% by weight. The surfactant content of these compositions preferably ranges from 5 to 40% by weight.

The compositions according to the invention themselves are in solid or liquid form.

Solid forms of the compositions according to the invention may include dusting powders (up to 100 S active ingredient), granules, in particular granules obtained by extrusion, compression, impregnation of a granular carrier or powder granulation (in the latter cases the active ingredient content of of these granules (0.5 to 80%), tablets or effervescent tablets.

The compounds of the formula I can also be used in the form of dusting powders; it is also possible to use a composition comprising 50 g of active ingredient and 950 g of talc; it is also possible to use a composition comprising 20 g of active ingredient, 10 g of finely divided silica and 970 g of talc; these components are mixed and ground together and the mixture is then applied by dusting.

As the liquid form of the compositions, mention may be made here of the forms intended to form the liquid compositions immediately before

9, for example, dispersible concentrates, emulsifiable concentrates, pension concentrates, aerosol, wettable powders for spraying), pastes or gels.

in water of earth, sus (or powders)

Emulsifiable or soluble emulsions contain from 10 to 30% of the active ingredient, solutions which are ready for application, concentrates of the most often being emulsified or contain from 0.001 to 20% of the active ingredient.

The emulsifiable concentrates may optionally contain, in addition to the solvent, 2 to 20% of suitable additives, such as stabilizing agents, surfactants, penetrating agents, corrosion inhibitors, colorants or other additives mentioned above.

By dilution with water, emulsions with any active compound concentration, which are particularly advantageous for application of the crop, can be obtained from these concentrates.

In the following, examples of the composition of two emulsifiable concentrates will be given.

i. an example of an emulable concentrate

- Active substance

- Alkali metal dodecylbenzenesulfonate

- Oxyethylenated nonylphenol containing 10 molecules of ethylene oxide

- Cyclohexanone

Aromatic solvent added to

400 g / l 24 9/1 1 6 9/1 200 g / l 1 i tra.

. an example of an emulable concentrate

-Effects 2 5 0 g

- Epoxy vegetable oil 25 g

- Mixture of arylsulfonate and polyglycol ether and fatty alcohols 100 g

-Dimethylformamide 50 g

-Xylene 575g.

Suspension concentrates, which are also sprayable, are prepared so as to form a stable, liquid, non-sedimented product, which concentrates usually contain 10 to 75% active ingredient, 0.5 to 15% surfactants, 0.1 to 10% % of thixotropic agents and 0 to 10% of suitable additives such as antifoams, corrosion inhibitors, stabilizing agents and penetration agents, and as carrier a water or organic liquid in which the active ingredient is insoluble or substantially insoluble. Certain organic solids or inorganic salts may be dissolved in the carrier as a function of preventing sedimentation or freezing of water. An example of such a suspension concentrate will be given below.

Example of a dry concentrate

- Active substance 5 0 0 g

- Polyethylated tristyryl 1 phenyl phosphate 50 g

Polyethylated alkylphenol 50 g

Sodium polycarboxylate 20 g

-Ethylene glycol 50 g

- Oraanopolysoxane oil (antifoam) 1 g

- Polysaccharide i 1.5 g

-Water 316.5 g.

Wettable powders (or powders for spraying) are usually formulated to contain 20 to 95% active ingredient, in addition to a solid carrier, further comprising 0 to 30% wettable powder, 3 to 20% dispersant and optionally 0.1 to 10%. % of one or more stabilizing agents and / or other additives such as penetrating agents, adhesives, anti-aggregating agents and coloring agents. In order to obtain powders intended for spraying or wettable powders, the active ingredient is intimately mixed in suitable mixers with the other ingredients of the composition, after which the resulting mixture is ground in a mill or other suitable disintegrator. The powders thus obtained have advantageous wettability and suspensibility. They may be at any desired concentration in water and C in water, and the suspensions thus obtained may be advantageously used in particular for application to plant leaves.

Compositions with a paste consistency can be prepared instead of wettable powders. The conditions under which these pastes are prepared and the methods for their preparation are analogous to the conditions and methods for the preparation of wettable powders intended for spraying.

The following are five examples of compositions of wettable powders (or powders for spraying).

i. an example of a wettable powder

-The active substance 50¾

- Ethoxylated fatty alcohol (wetting agent) 2,5%

- Ethoxylated phenylethylphenol (dispersant) 5%

-Chalk (inert carrier) 42.5¾.

Example 2 of a wetting powder

-Active substance. 10¾

- C 13-branched synthetic oxoalcohol, ethoxylated with up to 10 molecules of ethylene oxide (wetting agent) 0,75¾

- Neutral 1 ignosu 1 calcium phonate (dispersing agent 12¾

- Add calcium carbonate (inert carrier) to. 100%.

3. an example of a wettable powder

This wettable powder contains the same ingredients as the wettable powder of the preceding example in the following amounts:

-Efficiency 7 5%

- Wetting agent 1,50%

-Dispersing agent 3%

- Add calcium carbonate (inert carrier) to 100% wettable powder

-Efficiency 90%

- Ethoxylated fatty alcohol (wetting agent) 4%

- Ethoxylated phenylethylphenol (dispersing agent) 6%

Example 5 of wettable powder

- Active substance

- Anionic and non-ionic surfactant mixture (wetting agent)

- L ignosu1 sodium phonate (dispersing agent)

- Kaolin (inert carrier)

0%

2.5%%

42.5%.

The invention also includes aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or an emulsifiable concentrate according to the invention with water. These emulsions may be water-in-oil or oil-in-water emulsions and may have a consistency such as mayonnaise.

The compounds of the invention may be formulated in a form of from about 1 to about 90%, essentially consisting of water dispersible granules, which are also within the scope of the invention. These dispersible granules having a bulk density of about. 0.3 to 0.3 have a particle size in the range of about 150 to 2000, preferably 300 to 1500, micrometers. The active ingredient content of these granules is usually from 25 to 90%. The remainder of the granules is a solid filler and optionally a surfactant imparting granular dispersibility in water. These granules may be of two basic types, depending on whether the filler is soluble or insoluble in water. Where the filler is water-soluble, the binder may be an inorganic or organic substance. Excellent results have been obtained in this respect with urea, in the case of a water-insoluble binder, the binder preferably consists of an inorganic substance such as kaolin or bentonite. Then, the presence of surfactants (in an amount of 2 to 20%, based on the weight of the granules) is preferred, of which more than half is, for example, at least one dispersant of substantially anionic type such as alkali metal phonate or an alkaline earth metal or alkaline earth metal phonate, while the residual surfactant is composed of nonionic or anionic wetting agents such as alkali metal and alkaline earth metal phonates.

In addition, the granules may contain (although not necessary) other ingredients, including in particular defoaming agents.

Said granules according to the invention can be prepared by mixing the necessary ingredients and then granulating the mixture obtained by one of the known techniques (granulator, fluid bed, sprayer, extruder). The preparation of the aranuli is usually completed by grinding the obtained granulate and sieving the sieves with the abovementioned particle size. Granules prepared by granulating the carrier and optionally additives and subsequently impregnating the granules thus obtained can also be used to contain the active ingredient composition.

The granules are preferably obtained by extrusion, the process of which is given in the following first example d of the dispersible granulate.

1. an example of a dispersible granulate

90% by weight of the active ingredient and 10% by weight of urea in the form of beads are mixed in the mixer. This mixture is then ground in a rotary disintegrator. The powder obtained is moistened with about 5% by weight of water. This wet powder is then extruded in a perforated drum extruder. The obtained granules are dried, crushed and screened to retain only granules with a particle size between 150 and 2000 microns,

2. an example of an dispersible granulate

The following ingredients are mixed in the blender:

- Active substance 75%

- Wetting agent (sodium alkylnaphthalenesulfonate) 2%

- Dispersant (sodium polynaphthalenesulfonate) 8%

- Water insoluble inert filler (kaolin) 15%.

The mixture is then granulated in a fluidized bed in the presence of water, then dried, crushed and screened to retain granules having a particle size between 0.15 and 0.80 mm. These granules may be used alone or in the form of a solution or dispersion in water at the desired application concentration. These granules may also be used to prepare a combination with other active ingredients, in particular fungicides, in the form of wettable powders or granules or aqueous suspensions.

With respect to the compositions which are suitable for storage and transport, the compositions most preferably contain 0.5 to 95% by weight of active ingredient.

Also within the scope of the invention is the use of the compounds of the invention for controlling fungal plant diseases by preventive or curative treatment of these plants or the environment in which they grow.

Said up to 5 kg / ha and the compounds can be used advantageously in doses of 0.005, in particular in doses of 0.01 to 1 kg / ha.

Claims (7)

PATENT CLAIMS 1. 2-Alkoxy-2-imidazol-5-one compounds of formula I // (I) R ^J wherein is an aryl radical from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolinyl, and the sack and no 1 s alkylcarbonyl and methylpiperazino 1éndioxyfeny1 ov, group, each of which is optionally substituted with groups selected from the group consisting of meanings 1-3 R ⁶ represents an alkyl or haloalkyl group containing 1 to 3 carbon atoms, wherein: R - may additionally be taken together to form a carbocyclic group containing from 5 to 7 atoms, may be fused with groups each of the carbon atom to which they are heterocyclic, wherein the cyclic phenyl group and these groups may be optionally substituted with 1 to R® 3 groups selected from the group consisting of meanings means an alkyl or haloalkyl-containing group II 1 to 3 carbon atoms R ^{@ 1} represents an aryl group selected from the group consisting of phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolinyl, all-ynyl, and methylenedioxy of these groups is optionally substituted with 1 to 3 groups from the group consisting of R ^e , R ^p is H, formyl, acyl of 2 to δ carbon atoms, aroyl, alkoxycarbonyl of 2 to δ carbon atoms, an aryloxy carbonyl group, an alkylsulfonyl group or an arylsulfonyl group, R ^e stands for a halogen atom, or - an alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, cyanoalkylthio or alkylsulfonyl group having 1 to 6 carbon atoms, or - cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio or a (1-6) thienyl group containing from 3 to 6 carbon atoms, or a nitro group or a cyano group or a thiocyanato group and / or - an amino group which is optionally mono- or disubstituted by an alkyl or acyl group containing 1 to 6 carbon atoms or an alkoxycarbonyl group containing 2 to 8 carbon atoms, a phenyl group, a phenoxy group, a phenylthio group, a phenylsulfonyl group or a pyridyloxy group, these groups being optionally substituted by one or more substituents selected from the group consisting of: -halogen, - alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, or (III) an alkylsulfonyl group having 1 to 6 carbon atoms, - cycloalkyl, halocycloalkyl, alkenyl, alkynyl, alkenyloxy-, alkynyloxy-, alkenylthio-, alkynyl-thio-3-C6-alkynyl, - nitro, cyano or thiocyanato, - an amino group which is optionally mono- or disubstituted by an alkyl or aryloxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 2 to 6 carbon atoms, and a phenyl group, a phenoxy group, a phenyl group, a phenylsulfonyl group or a pyridyloxy group, and salts thereof. Compounds according to claim 1 of the general formula II in which R až to R majú have the meanings given for the general formula I. A process for the preparation of compounds according to claim 1, characterized in that the 2-alkylthio-2-imidazolin-5-ones of formula III are reacted with an alcohol R ³ OH in the presence of a strong base according to the reaction scheme: - IV S — R ' ³ N-P? á R ³ OH base _t solvent \ / R ^! Ii o 0 — R ³ “NR * R ^; wherein R ¹ , R ³ , R ³ and R ⁴ have the meanings given for formula (I) and R ' ³ represents an alkyl group having 1 to 3 carbon atoms. A fungicidal composition, characterized in that it contains, in combination with one or more agriculturally acceptable solid or liquid carriers and / or agriculturally acceptable surfactants, at least one active compound which is a compound of the formula I according to claim 1 or a salt thereof. δ. . A fungicidal composition, characterized in that, in combination with one or more agriculturally acceptable solid or liquid carriers and / or equally acceptable surfactants, one active substance, which is a compound of general formula (II) according to claim 2 or a salt thereof Fungicidal composition according to one of claims 4 or 5, characterized in that it contains 0.5 to 95% by weight of the compounds according to one of claims 1 or 2. 7. Method of treatment of crops which are infected with or susceptible to fungal diseases in fungal diseases, characterized by the fact that a preventive or curative application of an effective amount of a compound according to one of Claims 1 or of a compound according to Claims 4 to 6 is applied. The method of claim 7, wherein the effective dose is 0.005 to 5 kg / ha g. The method of claim 3, wherein the effective dose is 0.01 to 1 kg / ha. or their salt or compo- z n a č e n ý team that z n a č e n Ý team that