PL126290B1 - Method of manufacture of novel oxazolydinylacetamides and fungicide - Google Patents

Description

The subject of the invention is a method for preparing new oxazolidinyl acetamides and a fungicide containing these compounds as the active substance. The compounds produced according to the invention have the general formula 1, in which Rx is a group of formula 8, in which R7 and R8, independently of each other, represent an alkyl radical with 1 - 4 carbon atoms, a halogen atom or an alkoxy group with 1 - 4 carbon atoms, and R9 is a hydrogen atom, an alkyl radical with 1 - 4 carbon atoms or a halogen atom; R2 is a group with the formula CO—Rt 0, in which Rt 0 is an alkoxyalkyl radical, in which the alkoxy and alkyl parts contain 1 - 4 carbon atoms each, an alkylthioalkyl radical, in which both alkyl parts contain 1 - 4 carbon atoms, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrazolylmethyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl or haloalkyl with 1-4 carbon atoms; R3, R4, R5 and R0 independently of each other represent a hydrogen atom or an alkyl radical having 1-4 carbon atoms. When any of the substituents R3, R4, R5, R0, R7, R8 or R9 represent an alkyl radical or a group containing an alkyl radical (e.g. alkoxy group), the alkyl radical preferably contains 1-3 carbon atoms, e.g. methyl, ethyl, n-propyl or i-propyl. When R7 or R8 is halogen, it is F, Cl, Br or J , preferably F, Cl or Br, more preferably Cl or Br, and especially Cl. When R9 or R10 is or contains halogen, it is F, Cl, Br or J, preferably F, Cl or Br, especially Cl or Br. Preferred halogenated 2-furyl radicals for the substituent Rx 0 are monohalo-2-furyl radicals, e.g. 5-chloro-2-furyl or 5-bromo-2-furyl. Preferred haloalkyl radicals having 1 to 4 carbon atoms for the substituent Rx 0 are chloroalkyl or bromoalkyl radicals having 1 to 4 carbon atoms, e.g. chloromethyl, bromomethyl or C2H5CHBr-. Preferred halogenated 2-tetrahydrofuryl radicals for the substituent R10 are monohalogen radicals, especially monochloro- or monobromo-2-tetrahydrofuryl radicals, e.g. 5-chloro-2-tetrahydrofuryl. and alkyl groups for the R10 substituent are alkoxymethyl radicals with ol -3 carbon atoms in the alkoxy part. especially CH3 OCH2 - or C2 H5 OCH2 -. Preferred alkylthioalkyl radicals with 1 - 4 carbon atoms in each alkyl part for the R1 o substituent are alkylthiomethyl radicals with 1 - 3 carbon atoms in the alkyl part, e.g. CH3 SCH2 -. R! o preferably represents an alkoxyalkyl, 2-furyl or 5-halo-2-furyl radical. When one of the substituents R3 and R4 represents an alkyl radical with 1-4 carbon atoms, the other one preferably represents a hydrogen atom. When one of the substituents R5 and Ra represents alkyl radical with 1 - 4 carbon atoms, the second one preferably represents a hydrogen atom. A preferred group of compounds prepared according to the invention are compounds of the formula Ia, in which R2' means -COCH2OCH3, -COCH2OC2Hs, -CO-/2-furyl/ or - CO-(5-halo-2-furyl), R7' and R8' independently represent CH3, Cl or Br, and R9' represents H, Cl, Br or methyl, R7' and R8' are preferably the same. The method according to the invention for preparing compounds of formula 1 consists in the fact that the compound of formula 2, in which Rl9 R3, R4, R5, R6 and Rt 0 have the meanings given above and Y is a halogen atom, is subjected to intramolecular condensation. Y is preferably an atom chlorine or bromine, especially chlorine. Intramolecular condensation reactions are carried out in a known manner. The reaction is exothermic. It can, for example, be carried out in an anhydrous medium, using as a solvent an ether such as dimethoxyethane, a hydrocarbon such as toluene or another solvent inert to the reaction conditions. The reaction temperature is not critical and can range from 0-100°C. Because the reaction is exothermic, it is usually started at room temperature and then gradually increases in temperature. The reaction is usually carried out in the presence of an acid-binding agent, such as sodium hydride, sodium amide or sodium alkoxide, e.g. sodium ethoxide. Intramolecular condensation reactions can also be carried out in a two-phase water-organic system, in the presence of an inorganic base, e.g. sodium hydroxide and, optionally, a catalytic amount of a layer transfer catalyst. The organic layer may be any inert, water-immiscible solvent such as hydrocarbons or halogenated hydrocarbons, e.g. xylene, toluene, o-dichlorobenzene or dichloromethane. Suitable layer transfer catalysts are quaternary ammonium compounds such as benzyltrimethylammonium bromide, quaternary phosphonium compounds such as benzyltriphenylphosphonium chloride or crown ethers such as 18-crown-6. The starting compounds of formula 2 are new compounds. They can be obtained by acylation of compounds of formula 3 in which Rt, R3, R4, R5, R' and Y have the meanings given above, with a compound of formula 4 in which R10 has the meaning given above and Z is a halogen atom, preferably chlorine or a group having the formula O-CORi 0, where Rt 0 has the meaning above. Solvents used for the acylation reaction are hydrocarbons such as toluene or halogenated hydrocarbons such as chlorobenzene. The reactions are conveniently carried out at temperatures of about 50-120° C. e.g. 80°C. Compounds of formula 3 can be obtained by converting compounds of formula 5, where Ri is as defined above, with compounds of formula 6, where R3, R4, R5, R6 and Y are as defined above, and X is halogen, preferably Cl. The conversions can be carried out at temperatures from about 0°C to about 10°C, in water or in an organic solvent inert to the reaction conditions, preferably in the presence of a base, e.g. an organic amine or sodium carbonate. Substances starting materials and reagents used in the above-described processes are either known or, if they are not known, they can be prepared in a manner analogous to the above-described or known processes. The compounds of formula 1 have fungicidal activity, in particular against phytopathogenic fungi, especially fungi of the order Oomycetas , as shown by the following tests. Test A. Fungicidal activity against Phytophtora infestans. Young potted potato plants (3-5 leaf stage) were sprayed with an aqueous suspension containing 0.003% (weight/volume) of a compound of formula 1, e.g. 2-methoxy-N - (2,6-dimethylphenyl)-N- (2-keto-3-oxazolidinyl)-acetamide (Preparation 1). Two hours later, the treated plants were inoculated with a spore suspension of Phytophtora infestans and transferred to a tent maintained at 100% relative humidity at an ambient temperature of 16°C and a day length of 16 hours. Disease inhibition was determined 4-5 days later by comparing treated plants with untreated, similarly inoculated plants. It was found that the tested compound caused a significant inhibition of fungal infection, without any signs of phytotoxicity towards the host plants. Test B. Fungicidal effect against Plasmopara viticola. Young, potted vine plants (3-6 leaf stage) were sprayed with an aqueous suspension containing 0.0008% (weight/ volume) of a compound of formula 1, e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide (Preparation 1) two hours later the treated plants were inoculated with a Plasmo spore suspension ¬ para viticola and transferred to a tent where the relative humidity was maintained at 100% with an ambient temperature of 15-22°C (varying over a 24-hour period) and a day length of 16 hours. Disease inhibition was assessed 6 days later by comparing treated plants with untreated, similarly inoculated plants. A significant inhibition of fungal infection was found for the tested compound, with no signs of phytotoxicity in relation to the host plants. Test C. Curative fungicidal effect against Plasmopara viticola. Young potted vine plants (3-6 leaf stage) were inoculated as in test B, while treatment with the compound , e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide (Preparation 1) occurred 3 days after inoculation. The incubation conditions were as described in test B. Disease inhibition was assessed as in test B. Significant control of the fungal infection by the tested compound was found. Test D. Fungicidal activity leading to complete eradication of Plasmopara viticola. The procedure for determining this type of activity of the compounds was the same as described in test C, except that the treatment was carried out 6 days after inoculation, when sporulation on the lower leaf surface had already been observed. Disease control was determined 7 days after administration of e.g. 0.012% 2-methoxy-N-(2,6-dimethylphenyl-N-/2-keto-3-oxazolidinyl)-acetamide (Preparation 1). The effect of inhibiting the growth of the zones already sporulating and the complete cessation of the spore formation was observed.Test £. Transfer to treated vine leaves. The cut vine leaves were treated by spraying with an aqueous suspension containing 0.012% of a compound of formula I, e.g. /- acetamide (Preparation 1), in such a way that only the lower half of the leaf was treated. Two hours after treatment, the entire leaf was inoculated with a spore suspension of Plasmopara viticola, and the leaves were placed in a tent where the relative humidity was maintained at 100% under the conditions described in Test B. Although only the lower half of the leaf was treated, the test compound was found to cause inhibition of the disease on the entire leaf. The experiment therefore showed that 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide (Preparation 1) was distributed on both sides of the leaf.TestF.Treatment soil In vivo study for Pythium aphanidermatum The fungus was grown in a sterile mixture of sand and corn flour in a volume ratio of 97:3, to which water was added in a volume ratio of 1:4. Cultivation lasted 4 days at a temperature of 25°C. Then the fungus was mixed with a semi-sterile mixture of peat and sand and treated with a suspension containing the active substance preparation to obtain a concentration of 10-160 ppm (e.g. 10, 40 and 160 ppm), calculated in terms of volume ¬ the thickness of the substrate. The substrate was transferred to pots with a diameter of 5 cm and sown with cucumber seeds. The pots were incubated at 24°C and 60-70% relative humidity in a greenhouse for 7 days, and the disease attack was determined by comparing the number of diseased plants with untreated, similarly infected control pots. The compound with code number 1 (Example I), used in the form of a wettable powder, causes complete control of the disease. Analogous tests as in test F, carried out for peas and sugar cane, gave similar results. It was found that each of the compounds listed in the examples below shows fungicidal properties and may be useful as a fungicide. Particularly beneficial fungicidal activity was found in the above tests for compounds of the formula Ia, in which R2' is COCH2OC2H5, R7' and R8' are CH3, R9' is Halbo R2' is CO- (2-furyl), R7' and R8' are CH3, R9' is H or R2' is CO- (5-bromo-2-furyl), R7' and R8' are CH3, R/ is H or R2' is COCH2OCH3, R7' and R*' are Cl, R9' is H or R2' is COCH2OCH3, R7* and R8' are CH3, R9' is 3-Br, especially for the compound of formula Ia. where R2' is COCH2 OCH3, R7' and R8' are CH3 and R9' is H. The agent according to the invention is used to combat phytopathogenic fungi, especially the order Oomycetes. The agent contains a fungicidal amount of the compound of formula 1 and is used to treat plants, seeds or soil.4 126290 Fungi of the order Oomycetes, against which the agent according to the invention has a particularly beneficial effect, belong to the genus Phytophtora and occur on plants such as potatoes, tomatoes, tobacco, citrus trees, cocoa trees, rubber trees, apples, strawberries, vegetables , ornamental plants, e.g. Phytophtora infestans on potatoes and tomatoes; fungi of the genus Plasmopara viticola on vines; genus Peronospora on plants such as tobacco, e.g. Peronospora tabacina on tobacco; Pseudoperonospora species on plants such as hop cones and cucumber, e.g. Pseudoperonospora humuli on hops; genus Bremia on plants such as lettuce, e.g. Bremia lactucae on lettuce, genus Pythium, causing blackleg and root rot in many plants such as vegetables, sugar cane, ornamentals and conifers, e.g. Pythium aphanidermatum on sugarcane; genus Sclerospora on plants such as sorghum and corn, e.g. Sclerospora sorghis on sorghum. The amount of preparation used depends on factors such as the species of fungus to be controlled, the time and type of administration and the amount and type of compound of formula 1 used. However, in general, satisfactory the results are obtained by local application, e.g. to crops or soil, at doses in the range of about 0.05 - 5 kg, preferably 0.1 - 3 kg of the compound of formula 1 per hectare of the treated place, the treatment being repeated if necessary. When used as a seed dressing, satisfactory results are obtained when administered at doses of about 0.05-0.5, preferably about 0.1-03 g of a compound of formula 1 per kilogram of seed. Compounds of formula 1 are preferably used in combination with fungicides acting against phytopathogenic fungi, against which the compounds of formula 1 are less or not at all active, which allows the control of a wider range of fungi than with compounds of formula 1. The fungicide according to the invention contains compounds of formula 1 in combination with an allowable in agriculture as a carrier or diluent. Moreover, in addition to the compound of formula 1 as the active substance, the composition may contain other active substances, such as fungicides. The agent may be in both liquid and solid form, e.g. in the form of a wettable powder, emulsion concentrate, water-dispersed suspension concentrate, dusting powder, granulate, preparation with delayed release of the active substance, and these preparations contain conventional carriers, diluents and /or additions. Such preparations are prepared by known methods. Sprayable preparations, such as water-dispersible concentrates or wettable powders, may contain surfactants, such as wetting or dispersing agents, e.g. fatty alkyl sulfates, ethoxylated alkylphenol or ethoxylated fatty alcohol. The preparations generally contain 0.01 - 90% by weight of the active substance, which is at least one compound of formula 1 or mixtures thereof with other active substances. Concentrated forms of the preparation usually contain 2 - 80 %, preferably 5-70% by weight of the active substance. Liquid preparations may contain 0.01 - 20% by weight, preferably 0.01 - 5% by weight of the active substance. The invention is illustrated by the examples below, in which the parts and percentages are given by weight and the temperature in °C. Preparation 1. Wettable powder 50 parts 2 -methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide is mixed with 2 parts of lauryl sulfate, 3 parts of sodium lignosulfonate and 45 parts of finely ground kaolinite with an average particle size of less than 5 microns. The wettable powder thus obtained is diluted with water to a concentration of 0.01 - 5% of the active substance before use. The obtained liquid can be used for spraying leaves or sprinkling roots. Preparation 2. Granules 0.5 parts of a binding substance (non-ionic surfactant) are injected into 94.5 parts of quartz sand in a drum mixer and the whole mixture is thoroughly mixed. Then 5 parts of powdered 2-methoxy-N/2,6-dimethylphenyl/-N-/2-keto-3-oxazHdinyl/-acetamide are added and mixing is continued until granules are obtained with particle sizes in the range of 0.3-0, 7mm. The granules can be used to introduce into the soil near the plants whose leaves are to be treated with the drug. Example I. Preparation of 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide (code no. 1).. 11.8 g (0.0375 mol) 2-/ 2-chloroethyl methoxyacetyl(-2-(2,6-dimethylphenyl)-hydrazinecarboxylate is added portionwise to a suspension of 2 g of sodium hydride (in the form of approximately 55% by weight in mineral oil) in 100 ml of absolute toluene, at room temperature, under cover nitrogen. The reaction temperature increases gradually during the addition to 40°. After the addition is complete, the mixture is stirred for 30 minutes without cooling and then cooled to 10°. The unreacted sodium hydride is decomposed with ethanol, and the obtained solution is washed with water, dried over MgSO4 and the solvent is removed under reduced pressure. The product obtained is recrystallized from ethanol and colorless crystals of the compound given in the title are obtained, melting point 103- 104°. The starting 2-(methoxyacetyl)-2(2,6-dimethylphenyl)-hydrazine carboxylate used in Example 1 was obtained as follows: A mixture of 14.7 g (0.06 mol) 2-/2,6- 2-chloroethyl dimethylphenylhydrazinocarboxylate and 16.2 g (0.1 mol) of methoxyacetic acid anhydride [/CH3OCH2CO/20] are stirred in 100 ml of dry toluene for 1 hour at 80°. After cooling, the mixture is washed with water, then with a 5% aqueous solution of NaHCO3 and again with water. The solution is dried over MgSO4 and the solvent is removed under reduced pressure to obtain the desired product. 2-Chlorethyl 2-(2,6-dimethylphenyl)-hydrazinocarboxylate used for the above synthesis is obtained as follows: To the mixture: 127 g (0.935 mol) of 2,6-dimethylphenylhydrazine 102.5 g (1.3 mol) of pyridine and 400 ml of water are added, at a temperature of 0-5°, 133.5 g (0.935 mol) of chloroformic acid 0-chloroethyl ester. After the addition is complete, the mixture is stirred for 2 hours at room temperature, the precipitate is filtered off, washed with water and dried. The obtained product is recrystallized with toluene and colorless crystals are obtained, melting point 74-75°. Example II. Preparation of 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-keto-3-oxazolidinyl)-acetamide (code no. 2). 236.1 g (0.75 mol) of 2-chloroethyl 2-(methoxyacetyl)-2-(2,6-dimethylphenyl)-hydrazinocarboxylate, 375 ml of xylene and 187 ml of water are mixed and 82.5 ml are added under external cooling. (0.82 moles) of an aqueous solution of sodium hydroxide (containing about 0.4 g of NaOH per ml) in such portions as to maintain the temperature of the mixture at about 20°. After the addition is complete, the mixture is stirred for 1 hour at 20° and for 2 hours at 0°. The precipitate is filtered off, washed and dried. The desired compound is obtained in the form of a slightly colored solid with an elution temperature of 102 - 103°. The starting 2-(mctoxyacet10)-2-(2,6-di) is obtained by heating (0.825 mol) 2-chloroethyl 2-(2,6-methylphenyl)-hydroxyasylate in 500 ml of xylene to 80 ° and adds to hotX&^? 5.2-methoxyacetic acid chloride in 250 ml of xylene, prepared in situ by treating 73500826 mole of 2-methoxyacetic acid in 250 ml temperature 80°, within 2 hours. The mixture is heated for 30 minutes at 80° and then proceeds as described in Example 1. 2-Chlorethyl 2-(2,6-dimethylphenyl)drazinecarboxylate used in the above synthesis as the starting compound is prepared as follows: 0.1 mol) of 2,6-dimethylphenylhydrazine hydrochloride, 21.2 g (0.2 mol) of sodium carbonate in 50 ml of water and 50 mf of xylene are stirred for 30 minutes at room temperature and then cooled to a temperature of 5° . Then, maintaining the temperature at 5°, 14.3 g (0.1 mol) of chloroformic acid 2-chloroethyl ester are added within an hour. The mixture is stirred for another hour at 5° and at the end 100 ml of water are added. The precipitate formed is filtered off, washed with water and dried. The procedure is continued as described in Example I. In a manner analogous to that described in Examples I and II, the following compounds of formula 1 are prepared. 1 Compound code number 3 4 5 6 7 8 9 Ra H H H H H H H R, H H H H CH3 H H Rs H H H H CH3 H H R« H H H H H H H R7 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Rs CH3 Cl CH3 CH3 CH3 CH3 CH3 R9 H H H 4-C1 H H H Rio CHj OC2 H5 CH2OCH3 formula 9 CH2OCH3 CH2OCH3 CHj SCH3 CH2C1 Melting point Cc) 62-4 99-100 190-1 1 107-9 113-5 1 134-6 |6 126 290 1 Compound code number 1 10 1 H 12 13 14 15 16 17 18 19 20 1 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 Rl H H H 1 H H H H H H H H H H H H H H H H H H H H H H H H H H . H H H H H H H H R4 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Rs H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H R7 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Cl Cl Cl CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 C2HS CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 C2HS C2HS R8 Cl CH3 Cl Cl CH3 Cl CH3 CH3 CH3 CH3 Cl Cl Cl CH3 CH3 C2H5 CH3 CH? CH3 CH3 Br Br Br CH3 CH3 CH3 CH3 C2HS CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 C2H5 C2H5 R9 H H H H H H H H H H H H H 4-CH3 H 3-a 3-Br 3-Br 3-Br 4-CH3 4-CH3 4-CH3 H H 4- a 4-C1 H H H H H H H H H H H Rio CH2C1 CH2OCH/CH3/2 CH2OCH/CH3/2 pattern 9 CHjSCHs/n/ CH2SC4H9/n/ pattern 14 pattern 15 pattern 10 CH2OCH3 CH2C1 pattern 9 pattern 11 CH2OCH3 CH2C1 CH2OCH3 CH2OCH3 CH2C1 pattern 9 CH2OCH3 CH2C1 pattern 9 formula 16 formula 12 CH2C1 formula 9 CH2OCH3 CH2OC3H7/n/ CH2OC4H9/n/ formula 7 CH2OCH2CH=CL CH2OCH2C=CH formula 13 CH2OCH3 formula 11 formula 9 CH2C1 Melting point <°C) 135-6 166-7 oil | oil | 123-4 147-8 143-4 119-20 107- 9 142-4 173-4 139-41 oil | oil 90-2 96-7 182-3 145-8 125-6 124-6 193-4 90-4 149 - 52 rubber 1 164-5 109 - 12 oil | 2 98 -100 91-93 107-8 1 79-80 56 142-4 1 88-9 1126290 7 Compound code number 48 49 50 ¦ 51 52 53 Ra H H H H H H R4 H H H H H Rs H H H H H H R« H H H H H H R7 Br ClC2HS Br CH3 CH3 R8 Br Cl C2H5 Cl C2H5 CH3 R, H 4-C1 4-Q 4-CH3 H 4-Br Rio CH2OCH3 CH2OCH3 CH2OCH3 CH2OCH3 CH2OCH3 CH2OCH3 Melting point Cc) 150-2 128-9 114-6 131-4 ' 96-8 137-8 Patent claims 1. Method for preparing new oxazolidinyl acetamides of the general formula 1, in which Rx is a group of formula 8, in which R7 and R8, independently of each other, represent an alkyl radical with 1-4 carbon atoms, a halogen atom or an alkoxy group with 1-4 carbon atoms, and R9 represents a hydrogen atom, an alkyl radical with 1-4 carbon atoms or a halogen atom; R2 is a group with the formula CO-Rt 0, in which Rt 0 is an alkoxyalkyl radical, in which the alkoxy and alkyl parts contain 1 - 4 carbon atoms each, an alkylthioalkyl radical, in which both alkyl parts contain 1 - 4 carbon atoms, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrazolylmethyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl or haloalkyl radicals with 1-4 carbon atoms; R3, R4, R5 and R" independently of each other represent a hydrogen atom or an alkyl radical with 1-4 carbon atoms, characterized in that the compound of formula 2 in which Rt, R3, R4, Rs, R<5 and R10 are higher given meaning, and Y is a halogen atom, undergoes intramolecular condensation. 2. The method according to claim 1, characterized in that in the case of the preparation of compounds of formula 1, wherein R2 is -COCH2OCH3-COCH2 OC2H5, -CO-(2-furyl) or -CO-(5-halo-2-furyl), R3, R4, R5 and Ra represent a hydrogen atom, R7 and R8 independently of each other represent CH3, Cl or Br, R9 represents H. Cl.Br or CH3, the compound of formula 2 in which R3, R4, R5, R6, R7 is subjected to intramolecular condensation , R8 and R9 have the meanings given above, Y is halogen. 3. The method according to claim 2, characterized in that in the case of preparing compounds of formula 1, in which R7, R8, R9 and Rx 0 represent CH3, CH3, H and CH2 OCH3, respectively, the compound of formula 2, in which R7, R8, R9 and Rx0 are as defined above and Y is halogen. 4. A fungicide containing an active substance and an agriculturally acceptable carrier or diluent, characterized in that it contains as the active substance compounds of the formula 1, in which Rx is a group of the formula 8, in which R7 and R8, independently of each other, denote an alkyl radical with 1-4 carbon atoms, a halogen atom or an alkoxy group with 1-4 carbon atoms, and R9 denotes a hydrogen atom, an alkyl radical with 1-4 carbon atoms or a halogen atom; R2 is a group with the formula CO—Rj 0, in which Rt 0 is an alkoxyalkyl radical, in which the alkoxy and alkyl parts contain 1 - 4 carbon atoms each, an alkylthioalkyl radical, in which both alkyl parts contain 1 - 4 carbon atoms, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrazolylmethyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl or haloalkyl radicals with 1-4 carbon atoms; R3, R4, R5 and Rc independently of each other represent a hydrogen atom or an alkyl radical with 1 - 4 carbon atoms.126 290 r: o R, R.N N ^0 A A R3 R4 R5 R6 FORMULA 1 R / / \ R N r: o 8 MODEL 1a HO R„ RK R, R, I ii V6 V N—C—O—C C—Y R—N 'C—R 10 O MODEL 2NH 126 290 o c o R5 R6 R3 RL —c c— Y MODEL R O C- 10 MODEL 4 R1—NH—NH2 FORMULA O Re RR Rq R/ —c c— ¦Y FORMULA126 290 CH20CH C2H5 CH3 FORMULA 7 R / 7 / FORMULA 8 \/0 FORMULA 9 \/0\/Br FORMULA 10126 290 /<=, CH, N 2 \: PATTERN 11 O PATTERN 12 CH2 PATTERN 13126 290 CH—C,H, I Br PATTERN U CH—CH3 Cl PATTERN 15 CH0CH3 CH3 PATTERN 16 Printing Studio UP PRL. 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Claims (4)

1. Patent claims 1. Method for preparing new oxazolidinyl acetamides of the general formula 1, in which Rx is a group of formula 8, in which R7 and R8, independently of each other, represent an alkyl radical with 1-4 carbon atoms, a halogen atom or an alkoxy group with 1 - 4 carbon atoms, and R9 is a hydrogen atom, an alkyl radical with 1 - 4 carbon atoms or a halogen atom; R2 is a group with the formula CO-Rt 0, in which Rt 0 is an alkoxyalkyl radical, in which the alkoxy and alkyl parts contain 1 - 4 carbon atoms each, an alkylthioalkyl radical, in which both alkyl parts contain 1 - 4 carbon atoms, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrazolylmethyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl or haloalkyl radicals with 1-4 carbon atoms; R3, R4, R5 and R" independently of each other represent a hydrogen atom or an alkyl radical with 1-4 carbon atoms, characterized in that the compound of formula 2 in which Rt, R3, R4, Rs, R<5 and R10 are higher given meaning, and Y is a halogen atom, undergoes intramolecular condensation. 2. The method according to claim 1, characterized in that in the case of the preparation of compounds of formula 1, wherein R2 is -COCH2OCH3-COCH2 OC2H5, -CO-(2-furyl) or -CO-(5-halo-2-furyl), R3, R4, R5 and Ra represent hydrogen, R7 and R8 independently represent CH3, Cl or Br, R9 represents H. Cl. Br or CH3, the compound of formula 2 is subjected to intramolecular condensation, in which R3, R4, R5, R6, R7, R8 and R9 have the meanings given above, Y is a halogen atom. 3. The method according to claim 2, characterized in that in the case of preparing compounds of formula 1, in which R7, R8, R9 and Rx 0 represent CH3, CH3, H and CH2 OCH3, respectively, the compound of formula 2, in which R7, R8, R9 and Rx0 are as defined above and Y is halogen. 4. A fungicide containing an active substance and an agriculturally acceptable carrier or diluent, characterized in that it contains as the active substance compounds of the formula 1, in which Rx is a group of the formula 8, in which R7 and R8, independently of each other, denote an alkyl radical with 1-4 carbon atoms, a halogen atom or an alkoxy group with 1-4 carbon atoms, and R9 denotes a hydrogen atom, an alkyl radical with 1-4 carbon atoms or a halogen atom; R2 is a group with the formula CO—Rj 0, in which Rt 0 is an alkoxyalkyl radical, in which the alkoxy and alkyl parts contain 1 - 4 carbon atoms each, an alkylthioalkyl radical, in which both alkyl parts contain 1 - 4 carbon atoms, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrazolylmethyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl or haloalkyl radicals with 1-4 carbon atoms; R3, R4, R5 and Rc independently of each other represent a hydrogen atom or an alkyl radical with 1 - 4 carbon atoms.126 290 r: o R, R. N N ^0 A A R3 R4 R5 R6 FORMULA 1 R / / \ R N r: o 8 MODEL 1a HO R„ RK R, R, I ii V6 V N—C—O—C C—Y R—N 'C—R 10 O MODEL 2NH 126 290 o c o R5 R6 R3 RL —c c— •Y MODEL R O C- 10 MODEL 4 R1—NH—NH2 MODEL O Re RR Rq R/ —c c— ¦Y MODEL126 290 CH20CH C2H5 CH3 MODEL 7 R / 7 / MODEL 8 \/0 MODEL 9 \/0\/Br MODEL 10126 290 /<=, CH,N 2 \: PATTERN 11 •O PATTERN 12 CH2 PATTERN 13126 290 CH—C,H, I Br PATTERN U CH—CH3 Cl PATTERN 15 CH0CH3 CH3 PATTERN 16 UP PRL Printing Workshop. Edition 100 copies. Price PLN 100 PL PL PL PL