Method for producing 1,2-benzisothiazolin-3-ones(options)

 

(57) Abstract:

The invention relates to a method for producing 2-alkylbenzoates, which includes the interaction bisimide formula 2 in water or water-containing organic liquid bisulfite or allocating the bisulfite agent with the formation of salts of the Rebellion and the transformation of the salt Riot in alkaline conditions in the 2-alkyl-BIT. R represents alkyl. Preferred R substituents are butyl, hexyl, 2-ethylbutyl, 2-ethylhexyl or cycloalkyl. The technical result is an increase in the yield of N-alkyl-BIT. 3 S. and 7 C.p. f-crystals.

The present invention relates to a method for producing 1,2-benzisothiazolin-3-ones and to the use of the compounds obtained as a technical biocides.

1,2-Benzisothiazolin-3-ones (called hereafter BIT ("BIT") has long been known, including their use as technical biocides.

There are three common ways of getting BIT, as described in the patent application UK N 848130.

The first method includes obtaining 2-halogensubstituted and its reaction with the primary amine of obtaining N-substituted BITS. 2 - Halogensubstituted usually obtained by splitting the dis is UPP carboxylic acid galodamadruga acid.

The second method includes obtaining 2-halogentated and cyclization of this compound in the presence of acid or alkali. Typically, 2-halogenoalkane get through the conversion of 2,2'-dithio-bis-benzoic acid in basamid and subsequent cleavage of disulfide bonds by halogen. Halogen is often chlorine provided by sulfurylchloride.

The third method involves disproportionation 2.2 dithio-bis-benzamide by heating in the presence of sodium hydroxide solution.

Due to the increased ambient pressure, there is increasingly a need to avoid methods that include the cleavage of disulfide bonds in Bismillah predecessors while getting BIT by halogen, as this may give pentachlorphenol, in particular pentachlorphenol. Thus, people have been searching for alternative ways of transformation of 2,2'-dithiobiurea (called hereafter "bisimide") in BIT by using smoke zero halogen cyclization.

One of such ways is the disproportionation bisimide in the presence of oxygen or produce oxygen agent, as described in Europatent 187349. This method gives a high yield of the actual BITS and 6 is also split using bisulphite, that results in the formation of salts of the Rebellion, which can then cilitates under alkaline conditions with getting BIT. This General reaction of obtaining salts Rebellion BITS described by the author Tyrrell (Tetrahedron Letters, 26, 1753 (1985)) using Bismillah predecessors, containing aminosalicyclic in the amide group. This publication provides only one example in which the salt Riot was obtained with a yield of 47% of bisimide with piperidinyloxy group imidazolidine. Baggaley al. in J. Med. Chem. 28, 1661-1667, 1985, described also receive two other derivatives of BITS containing N-ethylpiperidine and N-ethylpyrrolidin group, using the salt Riot as an intermediate product, however, the total output BITS from basamid was again low at 22% and 21%, respectively. Apparently, this method has not found further development, possibly due to the sensitivity of the method to the Deputy detected in the case of diphenyldisulfide, as shown in the publication Lecher (with coauthors) in J. O. C. 20, 475, (1955). It is reported that there have been high outputs salts Rebellion in the case of bis-(3-nitrophenyl) disulfide, bis-(2 - AMINOPHENYL) disulfide, bis-(2-benzoylamino) disulfide and a low yield in the case of diphenyldisulfide. No disulfide and 2,2'-dithio-bis - benzothiazole. Since the output salts Rebellion from diphenyldisulfide clearly affected by the nature of the 2-substituent, in particular, in the publication Lecher, there is no indication whether the presence of 2-carbonamide, as in bismilah, to give high outputs salts Rebellion.

Applicants discovered that some bisimide can be converted into the salt Riot with high yield by reaction with bisulfite and, in particular, to produce the bisulfite agent, and that the thus obtained salt Rebellion can be easily converted into BITS. When using this method, the output of the N-alkyl-a BIT higher than the yield obtained using the method described in Europatent 187349.

Accordingly, the present invention relates to a method for the BIT formula 1

< / BR>
which includes interaction bisimide formula 2

< / BR>
in water or water-containing organic liquid bisulfite, or allocating the bisulfite agent, or mixtures thereof;

if this

R represents hydrogen, cycloalkyl, alkyl, alkyl, substituted hydroxyl group, halogen, C1-6-alkoxygroup, carboxypropyl, carbonamide, sulfonamide, nitrile or aryl or optionally substituted aryl;

X represents halogen, a nitro-group, Alcock is slow and represents preferably, C1-20-alkyl, preferably - C1-12-alkyl, and in particular WITH1-8-alkyl. Examples of such groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, amyl, isoamyl, n-hexyl, isohexyl, 2-ethylbutyl, n-heptyl, n-octyl, isooctyl, 2-ethylhexyl, n-decyl and n-dodecyl.

When R is zilouchian, alicyclic ring contains preferably up to 8 carbon atoms, as cyclopropyl and especially cyclohexyl.

When R is aryl, it contains preferably up to 10 carbon atoms, and especially preferably, when R is a phenyl.

When R is substituted aryl, the Deputy may be the same as that described in the case of the substituted alkyl.

When R is alkyl, substituted aryl, the aryl group is preferably phenyl, and especially benzyl, and preferably 2-phenylethyl. The phenyl ring in these substituted alkyl groups itself can also be substituted as described in the case of substituted aryl, but preferably when it is unsubstituted.

Halogen denotes fluorine, iodine, bromine and especially chlorine.

Preferably, n is equal to zero.

Kind of the, what aka agent is a sulfur dioxide in aqueous-alkaline medium and, especially, metabisulfite.

The reaction bisimide bisulfite or allocating the bisulfite agent can be catalyzed by oxygen or such a metal as copper, iron and cobalt, which may be present as a salt.

When BIT 1 R represents H, BITS can be obtained in the form of its salt with an alkali metal or ammonia. Examples of alkali metals are potassium and especially lithium or sodium.

Particularly preferably, R represents unsubstituted alkyl or 2-phenylethyl.

Good results are obtained when R is a methyl, n-butyl, n-hexyl, isohexyl, n-octyl, 2-phenylethyl, 2-ethylbutyl and 2-ethylhexyl.

The bisulfite or metabisulfite is present, preferably in the form of a water-soluble salt such as a salt of an alkali metal or ammonium salt. Preferred alkali metals are lithium, potassium and especially sodium.

Preferred are metabisulfite, because in many cases it gives higher yields of salt Rebellion and, therefore, a BIT.

The amount of bisulfite or allocating the bisulfite agent sostavlyaya. As a rule, the use of a large excess of bisulphite or allocating the bisulfite agent does not benefit. Thus, the number of metabisulfite is, preferably, less than 8 mol, in particular less than 5 moles, per mole bisimide. Higher yields of N-alkyl-BITS received from 2.5 to 3 moles, for example, from 2.75 by moles, metabisulfite per mol bisimide. In the case of bisulfite its amount is preferably less than 10 moles, especially less than 8 moles, per mole bisimide.

As noted above, the environment in which beamed enter into interaction with bisulfite or allocating the bisulfite agent may be water, and found that it is effective reaction medium for the BIT (formula I, R represents N) and for N1-2-alkyl-BIT. However, for N-substituted BITS of the reaction medium, preferably, is an organic liquid.

The organic liquid may be hydrophilic or hydrophobic, but preferably when it is hydrophilic.

When the organic liquid is hydrophobic, it preferably is a solvent for bisimide, and may represent aliphatic hydrocarbon, chlorinated organic liquids are methylene chloride, chloroform, carbon tetrachloride, trichlorethylene, perchlorethylene, trichloroethane, n-heptane, petroleum ether, diethyl ether, ethyl acetate and toluene.

When the organic liquid is hydrophobic, bisulphite or allocating the bisulfite agent can be dissolved in water and turn basamid in salt Revolt by mixing the two phases. Sol Rebellion is water-soluble and remains in the aqueous phase, after which it can be easily separated by simple phase separation.

When the organic liquid is hydrophilic, it preferably represents a glycol, a ketone, carbitol, amide, sulfoxide, and especially alcohol. Examples of such solvents are ethylene glycol, diethylene glycol, propylene glycol, acetone, methyl ethyl ketone, methyl and ethylcarbitol, dimethylformamide, dimethylacetamide, dimethylsulfoxide, methanol, ethanol, propanol, isopropanol, butanol, Isobutanol and tert-butanol, including mixtures thereof. Methanol, ethanol and ethylene glycol are particularly preferred, in particular methanol.

It is preferable that the hydrophilic liquid contained sufficient water to dissolve the bisulphite or allocating the bisulfite agent. In the case of bisulfite - is above 20%, relative to the amount of organic liquid. It is preferable that the amount of water was less than 100%, preferably, less than 70%, and particularly preferably less than 50% relative to the weight of the organic liquid.

In the case of metabisulfite amount of water is preferably at least 1%, preferably at least 2%, and especially preferably at least 4% relative to the weight of the organic liquid. The amount of water is preferably less than 20%, preferably less than 15%, and especially preferably less than 12% relative to the weight of the organic liquid. Good results were obtained when the amount of water relative to organic liquid is from 6 to 10%, in particular about 8%.

Bisulphite or metabisulphite can be added to the organic liquid in the aqueous solution or suspension, but it is preferable to add them to bisimide in the organic liquid in the form of solids. This is particularly advantageous in the case of metabisulfite.

The formation of the salt Riot is very easy and can be done by heating bisimide, bisulphite and/or allocating the bisulfite agent in an organic liquid is Tim fridge in the water, organic liquid or mixture of organic liquids with water.

Sol Rebellion can be distinguished by any known technique in a manner such as filtration or evaporation of water, organic liquid or mixture of organic liquids with water. In one of the preferred ways to add hydrophobic liquid which is not a solvent for the salt Riot to remove hydrophilic liquid or a mixture of hydrophilic liquid water in the form of an azeotrope. Another preferred method, when the organic liquid is hydrophilic, is to add more water to make the separation/precipitation of salts of the Rebellion. Found that the latter method is especially effective for N - alkyl-BITS, containing more than three carbon atoms in the alkyl chain.

Examples of preferred hydrophobic liquids, which form azeotropic mixtures with water and/or hydrophilic liquid is xylene, toluene, hexane, cyclohexane and methylcyclohexane.

Preferred hydrophobic liquid which forms an azeotrope mixture is toluene.

Thus obtained Sol Rebellion may be subjected to conversion with high output, which hurt the eyes. Preferably, the alkali is a hydroxide, carbonate or bicarbonate of an alkali metal or ammonium. Preferred are the hydroxides. Preferred alkali metals are lithium, potassium and especially sodium.

The amount of alkali is relatively minor, but usually represents a large excess relative to the amount of salt Revolt. Preferably, the amount of alkali in aqueous solution sufficient to obtain a pH above 9, preferably above 11, especially over 13.

Cyclization of the salt Riot with the formation of the BIT occurs rapidly in the presence of alkali, and, in General, this reaction can be carried out at 20 - 30oC. at higher temperatures, as a rule, are not required.

When the salt Riot separated, it can be directly processed with alkali solution when N-substituted allocate BITS either in the form of oil, either in the form of solids.

When the salt Riot is a hydrophobic liquid in the form of a dispersion, the dispersion can be treated with an aqueous solution of alkali, however, as their education, the BIT is dissolved in a hydrophobic liquid. Then, the BIT can be distinguished by removing the hydrophobic liquid is dependent on the specific BIT, and its subsequent commercial use, it is sometimes convenient to choose a hydrophobic liquid, which BIT should then be entered, so it eliminates the need for pre-allocating BITS.

As noted above, basamid derived from 2,2'-dithio-bis-benzoic acid (referred to hereafter TBK (D)), which are often contaminated with polysulfides of the formula 3

< / BR>
where X and n are as defined above values; and

p is 1 or 2.

When DTBC containing these polysulfides, in turn beamed, became also contains such polysulfide impurities. When converting such bisimide in a BIT with the use of halogen for splitting bisulfide regard, the presence of these polysulfides has an adverse impact on the output BITS. The presence of polysulfides and other contaminants in bisimide may also result in undesirable color change a BIT.

Currently, it is found that these polysulfides can also undergo reaction with bisulfite or allocating the bisulfite agent with obtaining salts Rebellion with high yield and that the BITS received from the polysulfides or bisimide containing polysulfides, has a more acceptable color than BITS, obtained by cleavage of disulfide bonds by halogen.

includes the interaction of the polysulfide of formula 4 or bisimide formula 2, which contains a polysulfide of formula 4, in water or in an organic liquid containing water, bisulfite and/or metabisulfite or mixtures thereof.

< / BR>
In this formula, R, X and n have the above specified values.

When the polysulfide of formula 4 is present in bisimide in the form of impurities, its amount is preferably less than 50 wt.%, preferably less than 20 wt.%, especially preferably less than 10 wt.%, in relation to bisimido.

As noted above, one way of obtaining the BIT is in the interaction of 2-halogensubstituted with the primary amine or ammonia. 2-Halogensubstituted get through cleavage of the disulfide bond DTBC halogen and either simultaneous or subsequent formation of galodamadruga acid. If DTBC contains polysulfides, the products of the reaction with the primary amine or ammonia are BITS and mixed bisimide formulas 2 and 4. This output BIT is reduced. Presently discovered that these compounds BIT and mixed bisamides can be turned into high-quality BITS by processing mixtures bisulfite or allocating the bisulfite agent for the conversion of the BIT and mixed bisamides in sootle with another aspect, the present invention relates to a method for the BIT formula 1

< / BR>
which includes processing a mixture of a BIT of formula 1 and bisimide formula 5

< / BR>
where X, R and n are as defined above values;

and q is 0, 1 or 2;

in water or in an organic liquid containing water, bisulfite or allocating the bisulfite agent, or mixtures thereof.

BITS are known industrial biocides, and, in accordance with another aspect, the present invention relates to the use of BITS obtained by the method of the present invention, as industrial biocides, especially as fungicides for paint and fungicides for plastics.

The invention is further described in the following examples, where all quantities are given in parts by weight unless otherwise indicated.

Example 1

Obtaining N-n-butyl-BIT using metabisulphite

The crude mixture of dithio-1,2'-bis(N-n-butylbenzamide) (60 wt.%, on a dry basis, basamid and polysulfides, 13 wt.% N-n-butylbenzothiazole-3-it, the rest not identified) (12,8 parts), sodium metabisulfite (11,4 parts), methanol (59 parts) and water (5 parts) is heated, with stirring, under reflux in the course within 30 minutes, and then filtered. To the filtrate add toluene (65 parts) and remove most of the methanol and water by azeotropic distillation, resulting in a gain of salt Rebellion in the form of a suspension in toluene. To a suspension in toluene add water (100 parts) and increase the pH of the aqueous phase to a value of more than 13,25, adding 47% sodium hydroxide solution. After stirring for 30 min at 20-25oC Sol Rebellion completely cyclized to N-butyl-BIT, which is dissolved in the toluene phase. Toluene phase is separated, washed with water (2 x 25 pieces) and remove the toluene by evaporation. Get N-n-butyl-BITS in the form of a yellow oil (10,8). Output, relative to the crude bisimide, is 95% of theoretical.

Example 2

Obtaining N-n-butyl-BIT using bisulphite

A mixture of dithio-2,2'-bis-(N-n-butylbenzamide) (86,5% by weight, on a dry basis, the rest not identified) (4.0 parts), methanol (15,6 parts) and a solution of sodium bisulfite (58.5% of SO2that is 4.93 parts of sodium bisulfite, and 13.2 parts of water) is boiled, with stirring, under reflux for 2 hours. Then the reactants are cooled, stirred with decolorizing charcoal (0.1 part) for 10 minutes at 20-25oC and filtered. The solid is washed with methanol is sid sodium to increase the pH to a value of more than 13.5 and continue stirring for 30 minutes at 20-25oC to convert the salt Riot in a BIT. Then, the BIT is extracted with toluene (50 parts) and toluene phase is separated and washed with water (2 x 25 pieces). Finally, the toluene is removed by distillation and as a result, there N-n-butyl-BITS in the form of a pale yellow oil (2,42). Output per basamid is 70% of theoretical.

The example for comparison, AND

Obtaining N-n-butyl-BIT with oxygen

A mixture of dithio-2,2'-bis-(N-n-butylbenzamide) (58,8% by weight, on a dry basis bisimide, 9.2% of N-n-butyl-BIT, the rest is not identified) of 20.5 parts), water (200 parts), methanol (20 parts) and an aqueous solution of sodium hydroxide (47% sodium hydroxide; of 12.8 parts) stirred at 55oC for 24 hours, at the same time barbotine through the reaction mixture gaseous oxygen at a speed of 3 ml of gas per second.

Then the reactants are cooled and N-n-butyl-BIT extracted with dichloromethane (200 parts). The organic phase is separated, washed with water (2 x 110 parts) and dried over anhydrous sodium sulfate. Then the dichloromethane is evaporated and the residue N-n-butyl-BITS in the form of a dark oil (9,4). The output of 49.5%. This is much lower than the yield obtained using the method of example 2 and, especially, than the output in example 1.

oC, resulting Sol Rebellion cyclized with the formation of N-n-hexyl-BIT, which is soluble in the toluene phase.

Then add activated carbon (1,13 parts) in water (16 parts) and then the reactants stirred for 40 minutes at 40-45oC. After free filter remove the toluene layer washed with water and, finally, removing the toluene by distillation. Get the product as a pale yellow oil (24,72 part with a concentration of 96.8 per cent; output - 80.3% of theoretical).

Example 4

Obtaining N-2-ethylhexyl-BIT using metabisulphite

Connection receive in a manner analogous to the method described above in example 3, except that use dithio-2,2' what (23,93 part, output - 70,3% of theoretical).

Example 5

Obtaining N-2-ethylbutyl-BIT using metabisulphite

Connection receive in a manner analogous to the method described above in example 3, except that use dithio-2,2'-bis-(N-2-ethylbutyrate) (20,3 part 0,043 M) instead of Putilkovo analogue and 16,35 part of sodium metabisulfite instead of the number of metabisulfate specified in example 3.

Get the product as a dark yellow oil, which solidified upon standing (12,0 part, the output is 50% of theoretical). In this example, the output BIT is reduced due to the filtering toluene phase after cyclization benzamide predecessor, if there is no product.

1. Method for producing 1,2-benzisothiazolin-3-one formula 1

< / BR>
wherein the stage includes: (a) interaction bisimide formula 2

< / BR>
in water or an organic liquid containing water, bisulfite, or allocating the bisulfite agent, or their mixture with obtaining salt Rebellion and b) processing the salt Riot lye,

where R is cycloalkyl containing up to 8 carbon atoms, or C1-20-alkyl, optionally substituted by phenyl;

X is halogen, nitro, alkoxy or nitrile;

n = 0 - 4.

1-12-alkyl, optionally substituted phenyl.

4. The method according to p. 3, wherein R represents methyl, n-butyl, n-hexyl, n-octyl, 2-ethylbutyl, 2-ethylhexyl, isohexyl or 2-phenylethyl.

5. The method according to any of paragraphs.1 to 4, wherein allocating the bisulfite agent is a metabisulfite.

6. The method according to any of paragraphs.1 to 5, characterized in that the bisulphite or allocating the bisulfite agent is a solid.

7. The method according to any of paragraphs.1 - 6, characterized in that the organic liquid is hydrophilic.

8. The method according to p. 7, wherein the organic fluid is methanol.

9. Method for producing 1,2-benzisothiazolin-3-one formula 1

< / BR>
wherein the stage includes: (a) interaction of the polysulfide of formula 4

< / BR>
or bisimide formula 2 containing the polysulfide of formula 4, in water or an organic liquid containing water, bisulfite or allocating the bisulfite agent, or mixtures thereof, and b) processing obtained in stage a) product lye,

where R, X and n corresponds specified in paragraph 1;

p = 1 or 2.

10. Method for producing 1,2-benzisothiazolin-3-one formula 1

formula 5

< / BR>
where X, R and n correspond to those specified in paragraph 1;

q = 0, 1, or 2,

in water or an organic liquid containing water, bisulfite or allocating the bisulfite agent, or mixtures thereof, and b) processing obtained in stage a) of the product with alkali.

 

Same patents:

The invention relates to a method for producing 6-fluoro-1,2-benzisothiazole formula

(I) where R is a hydrogen atom, a lower alkyl or a group of the formula

orwhere R1means-Cho or - CN, namely, that on-halogenoalkane derivative of the formula:

where R has the above meanings, is subjected to the interaction with R3SH, where R3- benzyl, environment aprotic organic solvent, with the formation of the compounds of formula

(III)where R and R3have the specified values, which are subjected to interaction with a halogenation agent to obtain the corresponding sulfanilamide formula

(IV)Subjected to interaction obtained sulfanilamide with ammonia in the compounds of the formula

(I)

Polucheniya pharmaceutically active compounds, which can be used, for example, as antipsychotic agents and as inhibitors of reuptake of serotonin

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EFFECT: novel compounds have useful biological properties.

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FIELD: chemistry.

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SUBSTANCE: invention relates to novel compounds, which possess qualities to estrogen modulators, of general formula (1) or its pharmaceutically acceptable salt, where R1 represents hydrogen atom or (C1-C6)alkyl, -SO2NR7R8, phenyl (C1-C3)alkyl or (C1-C3)alkyl, substituted with 5-8-member heterocyclic radical, containing nitrogen atom; R2 and R3 each independently represents hydrogen atom or hydroxyl, halogen atom or (C1-C6)alkoxy; X represents O, S, SO, SO2 or NR4; R4 represents hydrogen atom or (C1-C6)alkyl, phenyl, phenyl(C1-C3)alkyl, (C1-C3)alkyl, substituted with 5-8-member saturated heterocyclic radical, containing one nitrogen atom, or group -COR7, -CO2R7 or -SO2NR7R8, where phenyl is not substituted or is substituted with at least one substituent, selected from group which includes hydroxyl, halogen atom or phenyl(C1-C3)alkoxy; Y represents direct bond, -(CR10R11)n- or -R10C=CR11-; R7 and R8 each independently represents hydrogen atom or (C1-C6)alkyl group; R10 and R11 each independently represent hydrogen atom or cyano, or group CONR7R8; n equals 1 or 2; A represents (C3-C12)cycloalkyl or phenyl, where phenyl is not substituted or is substituted with at least one substituent, selected from group which includes hydroxyl, halogen atom, (C1-C3)alkyl, (C1-C3)alkoxy; when X represents NR4, Y and R2 together with containing them indazole cycle can also form 1H-pyrano[4,3,2-cd)indazole; on condition that: 1) when X represents O, S or NR4, R1 represents hydrogen atom or (C1-C6)alkyl, and Y stands for direct bond, then A is not optionally substituted phenyl; 2) when X represents O, R1O represents 6-OH or 6-OCH3, Y represents direct bond and A represents cyclopeptyl, then (R2, R3) or (R3, R2) are different from (H, CI) in position 4, 5; 3) when X stands for O, R1O represents 6-OH, R2 and R3 represent H, and Y represents CH=CH, then A is not phenyl or methoxyphenyl; 4) when X represents SO2, A represents phenyl and R1O represents 5-or 6-OCH3, then (R2, R3) or (R3, R2) are different from (H, OCH3) in position 6- or 5-, compound not being one of the following: 3-phenyl-5-(phenylmethoxy)-1H-indazole; n-hydroxy-3-phenylmethyl-7-(n-propyl)-benz[4,5]isoxazole; 3-(4-chlorphenylmethyl)-6-hydroxy-7-(n-propyl)-benz[4,5]isoxazole; 6-hydroxy-3-(2-phenylethyl)-7(n-propyl)-benz[4,5]isoxazole; 3-cyclopropyl-6-hydroxy-3-phenylmethyl-7-(n-propyl)-benz[4,5|isoxazole; 3-cyclohexylmethyl-6-hydroxy-3-phenylmethyl-7-propyl-benz[4,5]isoxazole. Invention also relates to pharmaceutical composition, application and method of prevention and treatment of disease, where modulation of estrogen receptors is required.

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18 cl, 7 dwg, 8 tbl, 97 ex

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12 cl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to fungus control, specifically to 5-iodotetrazole derivatives , in which R1 denotes butylene, straight unsubstituted alkyl with 8-16 carbon atoms, straight or branched unsubstituted or mono- or multi-, identically or differently substituted alkyl with 1-8 carbon atoms, where the substitutes are or mono- or multi-, identically or differently substituted alkyl residues selected from a group comprising unsubstituted alkoxy or 1-6 carbon atoms and alkoxy with 1-6 carbon atoms, substituted with dioxalonyl, phenyl which is up to five times identically or differently substituted with halogen, alkyl with 1-4 carbon atoms, halogenalkyl with 1-4 carbon aotms, alkoxy with 1-3 carbon atoms, alkylthio with 1-4 carbon atoms, morpholinyl, except the following compounds: 1-tert-butyl-5-iodotetrazole, 1-ethyl-5-iodotetrazole, 1-methyl-5-iodotetrazole. Said 5-iodotetrazole derivatives are obtained by treating tetrazoles of general formula , in which R1 assumes values given above, with iodine in an organic solvent in the presence of a base and, if needed, in the presence of a diluent. The invention also relates to a fungicidal agent, containing 5-iodotetrazole derivatives of general formula , in which R1 denotes hydrogen, alkylene with 1-4 carbon atoms, straight unsubstituted alkyl with 8-16 carbon atoms, straight or branched unsubstituted or mono- or multi-, identically or differently substituted alkyl with 1-8 carbon atoms, where the substitutes are mono- or multi-, identically or differently substituted alkyl residues selected from a group comprising unsubstituted alkoxy with 1-6 carbon atoms and alkoxy with 1-6 carbon atoms, substituted dioxalonyl, unsubstituted phenyl, phenyl which is up to five times identically or differently substituted with halogen, alkyl with 1-4 carbon atoms, halogenalkyl with 1-4 carbon atoms, alkoxy with 1-3 carbon atoms, alkylthio with 1-4 carbon atoms, morpholinyl and at least one solvent or diluent, as well as auxiliary additives if necessary. The invention also relates to paint material containing compounds of formula (Ia).

EFFECT: said fungicidal agent can be used in a method of protecting plants and paint materials from attack and/or decomposition by fungi by exposing the fungi or habitat thereof to the said agent.

11 cl, 2 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: group of inventions refers to a method for preparing an immobilised 1,2-benzisothiazolin-3-one complex, an antimicrobial composition containing it and to using the above composition as an antimicrobial agent. The immobilised 1,2-benzisothiazolin-3-one is prepared by heating 1,2-benzisothiazolin-3-one and zinc chloride brought to the boiling point with partial condensation in C1-C4 alcohol to prepare a solution to be cooled and added with the immobilising effective amount of zinc oxide. The prepared mixture is brought to the boiling point with partial condensation, cooled to room temperature and filtered to prepare the immobilised 1,2 - benzisothiazolin-3-one/zinc oxide complex.

EFFECT: declared inventions provide producing the antimicrobial immobilised 1,2 - benzisothiazolin-3-one/zinc oxide complexes applicable as preserving agents due to their wash-out resistance.

12 cl, 4 dwg, 2 tbl, 22 ex

FIELD: biotechnologies.

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EFFECT: improving compound application efficiency.

19 cl, 29 ex

FIELD: chemistry.

SUBSTANCE: group of inventions relates to 1,2-benzizothiazolin-3-one or its salt, immobilised on zinc oxide (BIT/ZnO), method of obtaining complex of immobilised on zinc oxide 1,2-benzothiazolin-3-one and to application of 1,2-benzizothiazolin-3-one or its salt, immobilised on zinc oxide. Method of obtaining complex of immobilised on zinc oxide 1,2-benzothiazolin-3-one includes: obtaining mixture, which includes immobilising effective quantity of zinc oxide: liquid phase, which includes water, C1-C4 branched or non-branched alcohol or their mixture; and antimicrobial agent, dissolved in liquid phase and selected from the group, which consists of 1,2-benzizothiazolin-3-one, salts of 1,2-benzizothiazolin-3-one and their mixtures; and depositing antimicrobial agent with obtaining complex of 1,2-benzizothiazolin-3-one, immobilised on zinc oxide.

EFFECT: claimed inventions ensure obtaining antimicrobial complexes of immobilised 1,2-benzizothiazolin-3-one/zinc oxide, which are useful as preservatives because of their stability to washing out.

15 cl, 4 dwg, 12 tbl, 22 ex

FIELD: chemistry.

SUBSTANCE: invention relates to production of 1,2-benzisothiazolin-3-one or its sodium salt. Method comprises steps (i) heating a mixture of sodium sulphide hydrate and N-methyl-2-pyrrolidone, (ii) distillation of water from mixture and, optionally, at least part of N-methyl-2-pyrrolidone, leaving sodium sulphide with depleted water content and, optionally, water and/or N-methyl-2-pyrrolidone, (iii) introduction of at least one benzamide, substituted in position 2, selected from a group, consisting of 2-chlorobenzamide, 2-fluorobenzamide, 2-nitrobenzamide, 2-cyanobenzamide and 2-C1-6 alkoxybenzamide with a branched or linear chain, in sodium sulphide with depleted water content to form a composition containing 2-mercaptobenzamide or its sodium salt, and (iv) of oxidative cyclisation of composition, containing 2-mercaptobenzamide or its sodium salt, by reaction with a reagent selected from a group consisting of aqueous hydrogen peroxide, MCPBA (meta-chloroperoxybenzoic acid), peracetic acid, perbenzoic acid and perphthalic acid.

EFFECT: production of 1,2-benzisothiazolin-3-one and its sodium salt with good output and purity.

3 cl, 8 ex

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