FR2473043A1 - Fungicidal 3-anilino-oxazolidine-2-one derivs. - with systemic action and low phytotoxicity, useful against e.g. Plasmopoara viticola - Google Patents

Abstract

(A)Fungal infections on plants are controlled by treatment with oxazolidine derivs. of formula (I). (Z is R,R1,R2-substd. phenyl. R,R1 and R2 are H, halo or 1-4C alkyl or alkoxy. R3 is H or methyl. A is CH2 or CH(CH3). n is zero or 1. R4 is H, 1-5C alkyl (opt. halo substd.), 3-6C cycloalkyl, 2-5C alkenyl, ethynyl, halo (when n is 1), SCN, cyano, phenyl (opt.substd. by 1-5C alkyl or halo), 5-6 membered heterocycle with 1-3 hetero atoms, acetyl, alkoxycarbonyl, OR5, SR5 or NR5R6. R5 and R6 are each H, 1-5C alkyl, 2-5C alkenyl or alkynyl, phenyl,5-6 membered heterocycle with 1-3 hetero atoms, alkylsulphonyl or acetyl). (B) (I) are new cpds. provided that when (A)nR4 is methyl, R,R1,R2 and R3 are not all H. (I) are specified for use against Plasmopara viticola and Peronospora tabacina. They can be used curatively or for prevention, esp. at 100-250 g per hectare.

Description

NEW COMPOUNDS FROM THE CLASS OF 3-INO-OXAZOLIDIN-2-ONES
The present invention relates to novel compounds of the class of 3-amino-oxazolidin-2-ones; these compounds are provided with a high fungicidal activity, and have good compatibility with the higher plants that we want to defend against fungi or champions.

 The fungicidal compounds belonging to the class of N-phenyl-1,3-oxazolidin-2,4-diones have been described, for example, in the published Dutch patent application No. 68/17249 (Sumitomo), in the US Pat. French Patent No. 2,172,295 (BASF), and in the Italian patent application No. 20579 A / 78 in the name of the Applicant.

 The bactericidal and fungicidal activity of certain derivatives of aniline and of glycine which bear on the nitrogen atom has been described a phenyl radical with various substitutions and an acyl group of varied nature.

 More particularly, this acyl group may be an α or β-haloalkanoyl (patent application in the Federal Republic of Germany disclosed under No. 2,513,789 to CIBA-GEIGY), or an acetyl group substituted at a by a a sulfur or oxygen atom, which is in turn bound to groups of various natures (French Patent Application No. 7 510 722 from CIBA-GEIGY), or a 2-furoyl, 2-thienoyl or pyridyl- 2-carbonyl (patent application in the Federal Republic of Germany disclosed under No. 2,513,732 and 2,513,788 of CIBA-GEIGY).

Likewise, has also been described the microbial activity of methylalaninates on the nitrogen atom 2,6-dialkylphenyl and one of the following groups
cyclopropanoyl, acryloyl, crotonoyl (patent applications in Switzerland
Our. 4988/74 and 2 906/75).

 Other acyl aniline derivatives with fungicidal properties have also been described recently in Belgian Patent No. 863,615 (CIBA-GEIGY) and in the German patent application disclosed under No. 2,745,533 ( CHEVRON).

 The interest of carrying out research with a view to disposing of new acylaniline derivatives having a fungicidal action results from the need to have derivatives of acylanilines which have a high fungicidal activity at the same time as they do not give. phytotoxicity.

 In fact, some of the products already known, although they develop an excellent fungicidal activity, have proved however to be toxic vis-a-vis the plants that one wishes to protect against infections due to fungi.

 Damage due to phytotoxicity to the plants to be protected can hardly be avoided by the use of a dose of fungicidal compounds, which is the best compromise between the fungicidal activity of the compound and its phytotoxicity.

 In fact, in practical applications in the agricultural field, the amount of product that remains truly on the plant varies considerably depending on various factors such as, for example, climatic conditions (including the frequency of rainfall), accuracy and the frequency of applications made by the farmer, etc.

 It is therefore necessary to have fungicidal products having a good fungicidal activity, and at the same time offering a wide margin of safety, so that even large quantities of products do not cause any damage to the plants to be treated.

dans laquelle:
R, R1 et R2, identiques ou différents, sont un atome d'hydrogène, d'halogène,
ou des radicaux alkyle ou alcoxyle comprenant l à 4 atomes de carbone;
R3 est un atome d'hydrogène ou un radical méthyle;
A = -CH2-,

n est égal à O ou 1;
R4 est un atome d'hydrogène ou un radical alkyle comprenant 1 à 5 atomes de
carbone, éventuellement substitué par des atomes d'halogène;
cycloalkyle comprenant 3 à 6 atomes de carbone;
alkényle comprenant 2 à 5 atomes de carbone; éthynyle,
un halogène (lorsque n = 1); un groupe CN;SCN;
phenyle éventuellement substitué par des radicaux alkyles comprenant 1 à
5 atomes de carbone ou des atomes d'halogène;
des groupes hétérocycliques comprenant 5 ou 6 atomes, dont notamment 1 a
3 hétéro-atomes (en particulier: les groupes furyle, tétrahydrofuryle,
thiényle, pyrimidyle, pyridyle, inlidazolyle, pyrazolyle, triazolyle);
acétyle; C00-alkyle; -OR5 ; -SR5 ;

(R5 et R6 (identiques ou différents) étant un atome
d'hydrogène ou un radical alkyle comprenant
l à 5 atomes de carbone;
alkényle comprenant 2 à 5 atomes de carbone;
alkynyle comprenant 2 a 5 atomes de carbone;
phényle; un groupe hétérocyclique comprenant
5 ou 5 atomes dont 1 a 3 hétéro-atomes ;
un groupe S02-alkyle, ou acétyle, étant entendu qu'au moins un des radicaux R, R, R2 et R3 n'est pas un atome d'hydrogène lorsque -(A)n - R4 = CH3
La préparation des composés de formule générale (I) est effectuée à l'aide des procédés connus de 1 'organicien moyen.The subject of the present invention is, as new industrial products, the compounds having the general formula:

in which:
R, R1 and R2, identical or different, are a hydrogen atom, halogen,
or alkyl or alkoxyl radicals having 1 to 4 carbon atoms;
R3 is a hydrogen atom or a methyl radical;
A = -CH2-,

n is 0 or 1;
R4 is a hydrogen atom or an alkyl radical having 1 to 5 carbon atoms
carbon, optionally substituted with halogen atoms;
cycloalkyl having 3 to 6 carbon atoms;
alkenyl having 2 to 5 carbon atoms; ethynyl,
a halogen (when n = 1); a CN group, SCN;
phenyl optionally substituted with alkyl radicals comprising 1 to
5 carbon atoms or halogen atoms;
heterocyclic groups comprising 5 or 6 atoms, including 1
3 hetero atoms (in particular: furyl, tetrahydrofuryl,
thienyl, pyrimidyl, pyridyl, inlidazolyl, pyrazolyl, triazolyl);
acetyl; C00-alkyl; -OR5; -SR5;

(R5 and R6 (same or different) being an atom
of hydrogen or an alkyl radical comprising
1 to 5 carbon atoms;
alkenyl having 2 to 5 carbon atoms;
alkynyl having 2 to 5 carbon atoms;
phenyl; a heterocyclic group comprising
5 or 5 atoms including 1 to 3 hetero atoms;
an SO 2 -alkyl or acetyl group, it being understood that at least one of the radicals R, R, R 2 and R 3 is not a hydrogen atom when - (A) n - R 4 = CH 3
The compounds of the general formula (I) are prepared using methods known to the average organic.

For example, an arylhydrazine (3) can be prepared by reacting the corresponding aniline (1) with sodium nitrite (NaNO 2) in hydrochloric acid and then reducing the diazonium salt (2) thus obtained (Scheme 1 ,
Equation I, hereinafter), as described, for example, in the Journal of the American Chemical Society, 81, p. 4673 (1959).

 The arylhydrazine is then reacted with 2-haloethyl or 1-methyl-2-haloethylchloroformate (4) (in turn prepared by the action of phosgene on a halohydrin), in the presence of a base , and the intermediate (5) thus obtained is then cyclized in the presence of bases, so as to lead to obtaining the intermediate (6) (Scheme 1, Equation II, hereinafter).

This process has been described in the Journal of the American Chemical Society, 48, 1951 (1926).

 The intermediate product (6) is then condensed with the aid of the acyl halide (7) suitable, according to known techniques (Scheme 1, Equation 3).

The condensation reaction between the intermediate product (6) and the acyl halide (7) can be replaced by a similar reaction known in the technical literature, which makes it possible to introduce particular acyl groups.

peut être preparee par réaction du produit intermédiaire (6) avec du phosgène ou avec des halogenures d'.haloacétyle ou halopropionyle (tels que, par exemple,

respectivement), puis par substitution de l'atome d'halogène selon les techniques connues.For example, the compounds of general formula (I), in which the acyl part:
R4 = -OR5; -SR5;

may be prepared by reacting the intermediate (6) with phosgene or with haloacetyl or halopropionyl halides (such as, for example,

respectively) and then by substitution of the halogen atom according to known techniques.

peuvent être préparés par réaction du produit intermédiaire (6) avec un isocyanate de formule: R5 - N = C = o. Compounds of formula (I), in which the acylic part is and where: R4 = NHR5,

can be prepared by reacting the intermediate (6) with an isocyanate of the formula: R5 - N = C = o.

(A = CH2; R4 = acétyle), peuvent être préparés par réaction du produit intermédiaire (6) avec le dicéténe. The compounds of formula (I), in which the acylic part is:

(A = CH2; R4 = acetyl) may be prepared by reacting the intermediate (6) with dicetene.

[X est un atome d'halogène;
R, R11 R2, R3, R4, A et n ayant les signications indiquées ci-dessus pour la formule générale (I)]. DIAGRAM

[X is a halogen atom;
R, R 11 R 2, R 3, R 4, A and n having the meanings indicated above for the general formula (I)].

The reaction is carried out in an inert solvent in the presence of a hydrohalic acid acceptor base at the reflux temperature.

 The compounds of general formula (I) are provided with an excellent fungicidal activity with respect to phytopathogenic fungi and their action is both preventive (that is to say they prevent the deaths), as well as curative (that is, they even lose when the infection is already under development).

The most important class of phytopathogenic fungi that can be combated using the compounds according to the present invention is that of the Phytomycetes, which comprise:
PZasmopozva spp.,
Phytophttora spp.,
Peronospora spp.,
Pseudoperonospora spp., And
Phythium spp.

 The fungicidal compounds of the present invention are useful for controlling fungal infections on beneficial plants such as vineyards, tomatoes, tobacco, potatoes and other crops.

 These compounds have good systemic properties (i.e. they act on different parts of the plant), which makes it possible to apply them both on the leaves and in the soil.

 In addition, these compounds of general formula (I) prove to be compatible with the plants that it is necessary to protect against the attack of fungi.

 Most of the compounds of the general formula (I) show no sign of phytotoxicity at the amounts at which they have been tested, while the others show only a small phytotoxicity lower in all cases than that of the known fungicides.

 In common agricultural applications, the fungicidal compounds of formula (I) may be used as they are or in the form of suitable compositions comprising the compounds of formula (I) which form the active ingredient, as well as inert, liquid or solids and, optionally, surfactants and other additives.

 If desired, other active compounds, such as other fungicides, insecticides, plant growth regulators, etc. may be present in the compositions.

 The compounds can be formulated in accordance with known agricultural techniques such as powders, dusts, moisturizing powders, emulsifiable liquids, granules, etc.

 The quantities of compounds of formula (I) to be distributed for controlling fungal infections depend on many factors such as the active compound used, the type of composition or formulation used, the type of infection and its rate, the type of crop treated to protect from the action of fungi, climatic conditions and ambient humidity, etc.

 In general, the amounts of fungicidal compounds of formula (I) employed are between 10 and 500 g / ha, although it is particularly preferable that they are between 100 and 250 g / ha.

Other advantages and features of the invention will become apparent, in the remainder of the description, given by way of nonlimiting example, with reference to the appended drawings in which:
EXAMPLE 1
Preparation of N- (methoxyacetyl) -N- (2,6-dimethyl-phenyl) -3-amino-oxazolidin-2-one.

A- Preparation of 2,6-dimethylphenylhydrazine
107 g of 2,6-xylidine are poured dropwise into a solution of 220 ml of concentrated hydrochloric acid in 150 ml of water.

After cooling to a temperature of -5 ° C., the mixture is then added to a solution of 66 ml of NaNO 2 in 150 ml of H 2 O over a period of about 1 hour and with vigorous stirring.

 To the yellow-orange suspension obtained is added, at 0 ° C. and in about 4 hours, 450 ° C. of SnCl 2 · 2H 2 O in 600 ml of a 5N aqueous solution of HCl.

 The mixture is then kept stirring for 24 hours, while the temperature is allowed to return to about + 20 ° C. The solid product thus formed is separated by filtration, dissolved in 700 ml of H 2 O, and then treated with a solution of 230 g of NaOH in 300 ml of H 2 O at a temperature of the order of 10 to 15 C, after which it is extracted with diethyl ether (3 x 250 ml).

The ethereal extract, after washing with H 2 O and anhydrification with Na 2 SO 4, is then brought to a volume of 1500 ml with diethyl ether and then treated with
Anhydrous gaseous HCl, until complete precipitation of 2,6-dimethylhydrazine hydrochloride is obtained.

 The salt is then filtered and dried, thereby obtaining 409 of a white solid, having a melting point (PF) of the order of 205 to 207 ° C (with decomposition).

 By treatment with NaOH, 2,6-dimethylphenylhydrazine is obtained from the hydrochloride salt.

B - Preparation of 3- (2,6-dimethylanitine) oxazotidin-2-one
To 41.49 of 2-bromoethyl-chloroformate, prepared from phosgene and ethylenic bromohydrin, in -200 ml of benzene, the following reagents are added at 10 ° C.
36,59 2,6-dimethylphenylhydrazine (see point A), and
18.0g of pyridine in 100 ml of benzene.

When this addition is complete, the temperature is allowed to return to 20 ° C. with constant vigorous stirring.

 Pyridine hydrochloride is removed by washing with water.

The benzene solution is then washed again with HCl and then with water until a neutral pH is obtained, and then dried on
Na2SO4 and evaporated.

An oily product is thus obtained which, crystallized in the ligand, gives a slightly colored solid, having a melting point of 58 to 63 ° C., and which is formed of 1- (2,6-dimethylphenyl) -2- (5-bromoethyl) -oxycarbonyl hydrazine.

[The infrared spectrum (IR) of this compound leads to the following results:
v (C = O) = 1710 cm-1:
v (NH-CO) = 3180 cm -1;
v (NH-Ar) = 3340 cm -1].

 409 of this intermediate are dissolved in 500 ml of toluene and then treated with 169 tetramethylguanidine. The mixture is then heated at reflux temperature for 3 hours, with stirring.

After cooling, the mixture is washed with 200 ml of H 2 O, then with 100 ml of dilute HCl and finally with 200 ml of H 2 O.

 The combined aqueous phases are extracted with CH 2 Cl 2 (2 x 200 ml).

 The combined organic phases are rendered anhydrous on Na 2 SO 4 and the solvent is evaporated to obtain a solid residue which is crystallized from a mixture of ligroin and ethyl acetate (2/1).

 There is thus obtained 22.59 of 3- (2,6-dimethylaniline) -oxazolidin-2-one, having a melting point of the order of 107 to 110 C.

[The infrared spectrum (IR) of this compound leads to the following results:
. v (C = O) = 1770 cm -1;
. v (NH) = 3340 cm -1]
The cyclization reaction is repeated by dissolving the intermediate product having a melting point of 58 to 62 ° C., in ethanol containing sodium ethoxide, and then by refluxing the solution.

 After a similar treatment of the reaction mixture, the same intermediate having a melting point of the order of 107 to 110 ° C. is isolated.

 C. To 2 g of the intermediate product prepared as described in point B), in 70 ml of toluene and 0.2 ml of dimethylformamide, 1.1 g of methoxyacetyl chloride are added. The reaction mixture is then heated at the reflux temperature for 8 hours. After cooling, the reaction mixture is subjected to complete evaporation of the solvents. The residue, consisting of 2.9 g of a thick oil, is purified on a column of silica gel, the eluent being a mixture of benzene and ethyl acetate (in a ratio 1/1).

 Thus, after removal of the solvents, 1.1 g of a syrupy product, which crystallizes spontaneously and which, after recrystallization from the mixture ligroin / ethyl acetate (1/1), leads to obtaining lg of the compound the characteristics of which are recorded in Table l.

hereinafter (Compound No. 6).

[The infrared spectrum (IR) of this compound leads to the following results:
. v (N-CO-CH 2) = 1680 cm -1;
. v (N-CO-O) = 1780 cm -1).

EXAMPLE 2
By operating in a manner analogous to that described in Example 1, the compounds listed in Table I are prepared, hereinafter:
TABLE I

<tb> Compound <SEP> R <SEP> R1 <SEP> R2 <SEP> R3 <SEP> n <SEP>#<SEP><SEP> R4 <SEP> PF <SEP> IR <SEP> (3)
## EQU1 ## -1) <SEP>
<tb><SEP> 1 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> CL <SEP> 71-4 <SEP> 1690-1760
<tb><SEP> 2 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> C6H5 <SEP> 112-4 <SEP> 1680-1760
<tb><SEP> 3 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> 1.C3H7 <SEP> Oil <SEP> 1680-1770
<tb><SEP> 4 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> Cl <SEP> 88-92 <SEP> 1635- 1770
<tb><SEP> 5 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> C6H5 <SEP> Oil <SEP> 1670-1770
<tb><SEP> 6 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> OCH3 <SEP> 103-6 <SEP> 1680- 1780
<tb><SEP> 7 <SEP> H <SEP> H <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> OCH3 <SEP> 86-91 <SEP> 1690-1760
<tb><SEP> 8 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> O-CO-CH3 <SEP> Oil <SEP> 1690-1770
<tb><SEP> 9 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> OH <SEP> 135-8 <SEP> 1690- 1770
<tb><SEP> 10 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> O <SEP> - <SEP> CO-OCH3 <SEP> 116-9 <SEP> 1680-1730-1790
<tb><SEP> 11 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> H <SE> 132-5 <SEP> 1670- 1770
<tb><SEP> 12 <SEP> 2-CH3 <SEP> 6-CH3 <SEP> H <SEP> H <SEP> 1 <SEP> CH2 <SEP> OC6H5 <SEP> 109-12 <SEP> 1690- 1780
<tb> (1) The elemental analysis of all the compounds shows that they exhibit the
indicated structure.

 (2) The melting points have not been corrected.

(3) Only the bands corresponding to V C = O are recorded.

 (4, V OH = 3300 cm-1.

TABLE II
Curative activity against Peronospora of the vine by foliar application to
doses of 0.5%.

<Tb>

Compound <SEP> No. <SEP> Activity
<tb><SEP> 1 <SEP> 3
<tb><SEP> 2 <SEP> 3
<tb><SEP> 3 <SEP> 4
<tb><SEP> 4 <SEP> 4
<tb><SEP> 5 <SEP> 4
<tb><SEP> 6 <SEP> 4
<tb><SEP> 7 <SEP> 4
<tb><SEP> 8 <SEP> 4
<tb><SEP> 9 <SEP> 4
<tb><SEP> 10 <SEP> 4
<tb><SEP> 11 <SEP> 4
<tb><SEP> 12 <SEP> 4
<Tb>
EXAMPLE 3 Curative activity with respect to the Peronospora of the vine LPZasmopora viticole
(B. and C) BerZ and Tni].

 Dolcetto vine leaves, grown in pots in a conditioned environment stabilized at 25 ° C. and 60% relative humidity, are sprayed on the lower part of the leaves with an aqueous conidia suspension of Plasmopopa vitieola. (200,000 conidia / cm3).

 After 24 hours of treatment in an environment saturated with humidity, stabilized at 21 C, the plants are treated by spraying both sides with the products tested in a hydroacetonic solution at 20% acetone (volume / volume).

At the end of incubation (7 days), the infection rate is determined at sight on the basis of the following scale of values:
0: none against, the infestation is equal to that of the plants
controls (infected but untreated plants);
reduction of 1 to 20% of the infestation;
2: reduction of 20 to 60% of the infestation;
3: reduction of 60 to 90% of the infestation;
4: reduction of the infestation greater than 90%.

On Table II, above, have been recorded the results obtained. t
EXAMPLE 4
Curative activity against tobacco Peronospora (Peronospora tabacina Adam).

 Burley tobacco leaves, grown in pots in a conditioned environment, are sprayed on the lower part of their leaves with an aqueous suspension of conidia of Peronospora tabacina (200 000 conidia / cm3).

 Six hours after this treatment in an environment saturated with moisture, the plants are transferred to a conditioned chamber stabilized at 20 C and 70% relative humidity, to allow the incubation of fungi.

24 hours after the infestation, the treatments are carried out by spraying on both sides of the tested product, in a 20% hydroacetone solution in acetone (volume / volume).

At the end of the incubation period (6 days), the infestation rate is determined visually on the basis of the scale of values given in Example 3.

The results tested are shown in Table III, below.

TABLE III
Curative activity by foliar application at 0.5% doses
on plants infested with Peronospora
tobacco.

<SEP> Compound <SEP> No. <SEP> Activity
<tb><SEP> 4 <SEP> 4
<tb><SEP> 6 <SEP> 4
<Tb>
TABLE IV
Phytotoxicity index for doses of 0.6%.

<Tb>

(2) "Ridomile" : il s'agit du composé consistant en N-(2, 6-diméthylphényl) -N-(l'-carto-
méthoxyéthyl)-méthoxyacétamide :

<SEP> Compose <SEP> No. <SEP><SEP> Index of <SEP> Phytotoxicity
<tb><SEP> 1 <SEP> o <SEP>
<tb><SEP> 3 <SEP> 10
<tb><SEP> 4 <SEP> O
<tb><SEP> 6 <SEP> O <SEP>
<tb>"Furataxle"<SEP> (1) <SEP> 100
<tb>"Ridomite"<SEP> (2) <SEP> 60
<tb> (1) "Furalaxyl": this is the compound consisting of
N- (2,6-dimethylphenyl) -N ~ (1'-carbo
methoxyethyl) -2-formoyl amide:

(2) "Ridomile": this is the compound consisting of N- (2,6-dimethylphenyl) -N- (the
methoxyethyl) -methoxyacetamide:

EXAMPLE 5
Determination of the phytotoxicity rate
Leaves of Dolcetto vine plants, grown in pots in a conditioned chamber stabilized at 25 ° C. and at 60% relative humidity, are treated by spraying on both sides with a 20% solution of hydroacetonic acid. acetone (volume / volume) of the products tested.

 After 7 days, the rate or degree of phytotoxic symptoms is determined at sight according to the scale of values by indices ranging between 100 (for totally damaged plants) and O (for healthy plants).

The corresponding data are given in Table IV, below, by comparison with the phytotoxicity index of the two compounds which have recently been placed on the market, namely:
"Furataxyte" (British Patent Number 1,448,810, CIBA-GEIGY), and
"Ridomile" (French Patent Application No. 2,267,042, CIBA-GEIGY).

 Of course, the present invention is not limited to the examples and embodiments mentioned above; it is capable of numerous variants accessible to those skilled in the art, depending on the intended applications and without departing from the spirit of the invention.

Claims (16)

 1. As new industrial products, the compounds of general formula (I):

 in which: R, R1 and R21, which are identical or different, consist of a hydrogen atom,  or halogen, an alkyl or alkoxyl radical comprising 1 to 4 atoms  of carbon;  R3 is H or CH3; A is -CH2-;

 n is O or I; and R4 is a hydrogen atom, or an alkyl radical comprising 1 to 5 atoms  carbon, optionally substituted with halogen atoms;  cycloalkyl having 3 to 6 carbon atoms;  alkenyl having 2 to 5 carbon atoms; ethynyl;  halogen (when n = 1);  a CN group, SCN; phenyle possibly substituted by radicals  alkyl having 1 to 5 carbon atoms or halogen atoms;  the heterocyclic group comprising 5 or 6 atoms, including 1 to 3 hetero atoms;  acetyl; COO-alkyl; -OR5; SR5;

 [R5 and R6, identical or different, consist of atoms  of hydrogen, an alkyl radical comprising 1  at 5 carbon atoms; alkenyl comprising  2 to 5 carbon atoms; alkynyl comprising  2 to 5 carbon atoms; phenyl;  a heterocyclic group having 5 or 6  atoms, including 3 hetero atoms;  SO2-alkyl, or acetyl]. it being understood that when - (A) n-R4 = CH3, at least one of the groups R, R1. R2 or R3, n is not hydrogen.  2. Compounds according to claim 1, characterized in that:  R = R1 = R2 = R3 = H, and  n = 1.  3. As a new industrial product, the compound: N-phenyl-N-chloroacetyl-3-amino-oxazolidin-2-one.  4. As a new industrial product, the compound: N-phenyl-N-phenylacetyl-3-amino-oxazolidin-2-one.  As a new industrial product, the compound: N-phenyl-N- (ss-methyl-) propionyl) -3-amino-oxazolidin-2-one. N-phenyl-N-methoxyacetyl-3-amino-oxazolidin-2-one.  6.- As a new industrial product, the conipose:  7. A compound according to claim 1, characterized in that:  R = R1 = CH3 'and R2 = R3 = H.  8. As a new industrial product, the compost: N- (2,6-dimethylphenyl) -N-chlorodetyl-3-amino-oxazolidin-2-one.  As a new industrial product, the compound: N- (2,6-dimethylphenyl) -N-phenylacetyl-3-amino-oxazolidin-2-one.  10. As a new industrial product, the compound: N- (2,6-dimethylphenyl) -N-methoxyacetyl-3-amino-oxazolidin-2-one.  11. As a new industrial product, the compound: N- (2,6-dimethylphenyl) -N-acetoxyacetyl-3-amino-oxazolidin-2-one.  12. As a new industrial product, the compound: N- (2,6-dimethylphenyl) -N-hydroxyacetyl-3-amino-oxazolidin-2-one.  13. As a new industrial product, the compound: N- (2,6-dimethylphenyl) -N-carbomethoxycarbonyl-3-amino-oxazolidin-2.  14. - From new industrial product, the compound:  .N (2,6-dimethylphenyl) - [N-méthoxyoxalyl] -3-amino-oxazolidin-2-one  15 .- As a new industrial product, the compound:  .N- (2,6-dimethylphenyl) -N-acetyl-3-amino-oxazolidin-2-one.  16 .- As a new industrial product, the compound:  N- (2,6-dimethylphenyl) -N-phenoxyacetyl-3-amino-oxazolidin-2-one.