Derivatives dimethylpolysiloxane, protective composition for wood (options), the method of protecting wood

 

(57) Abstract:

The invention relates to dimethylpolysiloxene General formula

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in which the radicals R1and R2may be the same or different, represents hydrogen, C2-C6- alkyl, C3-C6-cycloalkyl, C3-C6alkenyl,

C2-C6-quinil, C1-C3-halogenated, benzoyloxy group containing substituents, benzoylamino, which can also contain one or two Deputy, C2-C6-alkanolamines, C3-C6-cycloalkylcarbonyl, benzyl group which may contain substituents, the phenyl group with possible alternates, and other substituents, provided that at the same time R1and R2are not hydrogen atoms, the second condition is that one of R1and R2is not unsubstituted phenyl group when the other one represents a hydrogen atom, and the third condition is one of R1and R2in anthopology is not an aniline ring, C2-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkoxygroup when the other of them represents an atom of odor the effective amount of the compounds, the way to protect the wood, which consists in the application of a composition containing an effective amount of a compound of a specified formula. The invention also relates to a protective composition for wood, containing a mixture of at least one derivative compound of a specified formula, and at least one compound selected from 3-bromo-2,3-dead-2-propylethylene, 3-iodine-2-propynylbutylcarbamate and 4-chlorophenyl-3-improprieties. The invention allows to create a new preservative for wood. Its application is more secure, and, in addition, it can be used effectively at lower concentrations. The cost antiseptic low. Enhanced activity is also possible in combination with other components, suitable as antiseptics. 4 C. C. p. F.-ly, 9 tab., 2 Il.

The technical field

The present invention relates to new derivatives of dimethylpolysiloxane exhibiting excellent antimicrobial effect, to antiseptic for wood containing derived dimethylpolysiloxane as an active ingredient, and to a protective composition for wood, which is derived dimethylpolysiloxane as one and what about the already confirmed.

Prior art

To protect wood from rotting due to various fungi causing decay of the wood was formerly used various kinds of inorganic and organic compounds. However, these drugs have disadvantages, such as the impact on the human body due to their high toxicity, visible pollution, the necessity of their high concentration in the application, and cost.

With regard to compounds related to the derivatives of dimethylpolysiloxane of the present invention, compounds represented by the following formula, were described in the application Japanese Patent Kokai Appliction Sho 50-10376 as chemicals that will prevent damage to plants; in which, however, the radical R is limited to phenyl, nitrosamines by phenyl, carboxyphenyl by phenyl, phenylselenenyl by phenyl, methylsiloxane by phenyl, halogen-substituted by phenyl or methoxsalen by phenyl. Moreover, this patent is silent about other derivatives, and are not described activity of these compounds against wood destroying fungi.

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The invention

The aim of the present invention is to establish the van at low concentrations and/or the cost must be low.

Considering the situation mentioned above, the authors of the present invention considered derivatives furancarboxylic and intensively researched. The result of research of the applicants was that the new derivatives of dimethylpolysiloxane represented by the following formula I, are very useful as antiseptics for wood, and moreover, if the derived dimethylpolysiloxane as active f combined with any other commercially available antiseptic for wood, you may experience the effect of amplification steps, and can be manufactured protective composition for wood.

The compounds of the present invention are derivatives of dimethylpolysiloxane represented by the General formula

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In this formula, R1and R2the same or different and each represents a hydrogen atom; an alkyl group containing from 2 to 6 carbon atoms; cycloalkyl group containing from 3 to 6 carbon atoms; alkenylphenol group containing from 3 to 6 carbon atoms; alkylamino group containing from 2 to 6 carbon atoms; halogenation group containing from 1 to 3 carbon atoms; alkoxygroup containing from 2 to 6 ATO is holding from 1 to 6 carbon atoms in alkalinous component parts; the cyano; substituted amide group; alkoxycarbonyl group containing from 1 to 6 carbon atoms in the alkoxy part; benzoyloxy group, which can optionally contain from 1 to 2 substituents; benzoylamino, which can optionally contain from 1 to 2 substituents; alkanoyl-amino group containing from 2 to 6 carbon atoms; cycloalkylcarbonyl containing from 3 to 6 carbon atoms in cycloalkyl part; benzyl group which may optionally contain from 1 to 2 substituents; phenyl group which may optionally contain from 1 to 2 substituents; or alkoxycarbonylmethyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 2 to 5 carbon atoms in alkenylamine part; and R1and R2at the same time are not hydrogen atoms.

The present invention relates to the above compounds, antiseptic for wood and antiseptic compositions for wood containing derived dimethylpolysiloxane as an active ingredient.

Brief description of drawings

In Fig. 1 (a) - (e) show the minimum inhibiting concentration (in ppm - mn-1) soy is inhibiting concentration (m-1) connection example 2 in combination with various antiseptics for wood.

The best way to use inventions

In the said General formula I as an alkyl group containing from 2 to 6 carbon atoms, which is included in the definitions for R1and R2may be mentioned an alkyl group with a linear or branched chain, such as ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl or sec-hexyl, particularly preferably an alkyl group containing from 2 to 6 carbon atoms.

In the said General formula I as cycloalkyl group containing from 3 to 6 carbon atoms, which is included in the definitions for R1and R2may be specified cycloalkyl group, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; preferably, cycloalkyl group containing from 3 to 6 carbon atoms; and more preferably, cycloalkyl group containing from 5 to 6 carbon atoms.

In the said General formula I as alkenylphenol group containing from 3 to 6 carbon atoms, which is included in the definitions for R1and R2may be specified as hexenyl; preferably, Alchemilla group containing 3 to 4 carbon atoms; and more preferably, isopropanol.

In the said General formula I as alkenylphenol group containing from 2 to 6 carbon atoms, which is included in the definitions for R1and R2may be specified Alchemilla group, such as ethinyl, propargyl, 2-butynyl, 4-pentenyl or 2-hexenyl; preferably, Alchemilla group containing from 2 to 4 carbon atoms; and more preferably, ethinyl.

In the said General formula I as halogenoalkanes group containing from 1 to 3 carbon atoms, which is included in the definitions for R1and R2may be specified halogenation group, such as trifluoromethyl, trichloromethyl, pentafluoroethyl, 2,2,2-trichlorethyl, or 2,4-dichloropropyl; preferably, halogenation group containing from 1 to 2 carbon atoms; and more preferably trifluoromethyl.

In the said General formula I as alkoxygroup containing from 2 to 6 carbon atoms, which is included in the definitions for R1and R2may be specified alkoxygroup with a linear or branched chain, such as ethoxy, propoxy, isopropoxy, butoxy, pentox or exile the PAP, containing from 2 to 3 carbon atoms.

In the said General formula I as containing from 1 to 6 carbon atoms of alkoxygroup, part alkoxyalkyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 1 to 6 carbon atoms in the alkyl part, which is included in the definitions for R1and R2may be specified alkoxygroup with a linear or branched chain, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentox, neopentane or hexyloxy; preferably, alkoxygroup containing from 1 to 5 carbon atoms; and more preferably, alkoxygroup containing from 1 to 3 carbon atoms or containing 5 carbon atoms.

In the said General formula I as alkalinous group, part of alkoxyalkyl group containing from 1 to 6 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in alkalinous part, which is included in the definitions for R1and R2may be specified Allenova group with a linear or branched chain such as methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene or hexamethylene; preferably, Allenova group containing from 1 to 2 carbon atoms; and, which is included in the definitions for R1and R2may be specified monoalkylamines group, such as methylamide, ethylamide, isopropylated, butylamide, second-butylamide; dialkylamino group, such as dimethylamide, diethylamide, diisopropylamide, dibutylamine, di-sec-butylamide, methylethylamine, methylisophthalic, methylbutylamine, methyl-sec-butylamide, ethylisopropylamine, isopropylacrylamide, pyrrolidine or piperidine; optionally substituted phenylamide, such as phenylamide, 2-chlorpheniramine, 2,4-dichloraniline, 2-methylphenylene, 2-ethylvanillin or 4-methoxybenzylamine; preferably, methylamide, piperidine or phenylamide.

In the said General formula I as alkoxycarbonyl group containing from 1 to 6 carbon atoms in the alkoxy part, which is included in the definitions for R1and R2can be specified in a group that is formed above alkoxygroup containing from 1 to 6 carbon atoms, which is part of alkoxyalkyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 1 to 6 carbon atoms in the alkyl part, and a carbonyl group, such as group methoxycarbonyl, etoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, starbucksstarbucks, tert-butoxy-Kai from 1 to 3 carbon atoms in the alkoxy part.

In the said General formula I as a benzyl group, which may optionally contain from 1 to 2 substituents, which are included in the definitions for R1and R2can be specified optionally substituted benzoline group such as benzoyl, 2-chlorobenzoyl, 2,4-dichlorobenzoyl, 2-methylbenzoyl, 2,4-dimethylbenzoyl 4-ethylbenzoyl or 4-methoxybenzoyl; preferably benzoyl.

In the said General formula I as benzoylamino, which can optionally contain from 1 to 2 substituents, which are included in the definitions for R1and R2can be specified optionally substituted benzoylamino, which is formed by substitution in the amino group (groups) of the above benzene group, which can optionally contain from 1 to 2 substituents, such as benzoylamine, 2-chlorobenzylamino, 2,4-dichlorobenzidine, 2,4-dimethylbenzylamine, 4-methylbenzylamino, 4-ethylbenzylamine or 4 methoxybenzylamine; preferably benzoylamine.

In the said General formula I as alkanolamine containing from 2 to 6 carbon atoms, which is included in the definitions for R1and R2may be specified acetylamino, Propionaldehyde or isocaproate; preferably acetylamino.

In the said General formula I as cycloalkylcarbonyl containing from 3 to 6 carbon atoms in cycloalkyl part, which is included in the definitions for R1and R2can be specified in a group cyclopropanecarboxylate, cyclobutanecarbonyl, cyclopentanecarbonyl or cyclohexylcarbodiimide; preferably cyclohexylcarbodiimide.

In the said General formula I as a benzyl group, which may optionally contain from 1 to 2 substituents, which are included in the definitions for R1and R2may be mentioned benzyl, 2-methylbenzyl, 2,4 - dimethylbenzyl, 2-Chlorobenzyl, 4-methoxybenzyl or 4-ethoxybenzyl; preferably benzyl.

In the said General formula I as alkoxycarbonylmethyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 2 to 5 carbon atoms in alkenylamine part, which is included in the definitions for R1and R2may be mentioned methoxycarbonylamino, etoxycarbonyl-2-propanole, methoxycarbonyl-2-butylen or etoxycarbonyl-2-penttinen; preferably, methoxycarbonylamino.

Preferred with the and different, each of them represents a hydrogen atom; an alkyl group containing from 2 to 6 carbon atoms; alkenylphenol group containing 3 to 4 carbon atoms; alkylamino group containing from 2 to 4 carbon atoms; cycloalkyl group containing from 3 to 6 carbon atoms; alkoxycarbonyl group containing from 1 to 6 carbon atoms in the alkoxy part; alkoxyalkyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 1 to 2 carbon atoms in alkalinous part; cycloalkylcarbonyl, containing from 3 to 6 carbon atoms in cycloalkyl part; alkoxygroup containing from 2 to 4 carbon atoms; benzoyloxy group, which can optionally contain from 1 to 2 substituents; a benzyl group which may optionally contain from 1 to 2 substituents; or alkoxycarbonylmethyl group containing from 1 to 6 carbon atoms in the alkoxy part and containing from 2 to 5 carbon atoms in alkenylamine part; and R1and R2are not simultaneously represent hydrogen atoms. More preferred of these compounds include those in which: (2) R1and R2the same or different and each of them represents a hydrogen atom; alkalinetrio group, containing from 5 to 6 carbon atoms; alkoxycarbonyl group containing from 1 to 3 carbon atoms in the alkoxy part; alkoxymethyl group containing from 1 to 6 carbon atoms in the alkoxy part; cycloalkylcarbonyl containing from 4 to 6 carbon atoms in cycloalkyl part; benzoyloxy group; benzyl group which may optionally contain 1 Deputy; or alkoxycarbonylmethyl group containing from 1 to 3 carbon atoms in the alkoxy part and containing from 2 to 4 carbon atoms in alkenylamine part; and R1and R2are not simultaneously represent hydrogen atoms. Especially preferred of these compounds include those in which:

(3) R1is 3-alkyl group, containing from 2 to 6 carbon atoms; 3-alkoxycarbonyl group containing from 1 to 3 carbon atoms in the alkoxy part; 3-alkoxymethyl group containing from 1 to 3 carbon atoms in the alkoxy part; cycloalkylcarbonyl containing from 4 to 6 carbon atoms in cycloalkyl part; benzyl group which may be substituted by a methoxy group; benzoyloxy group; or alkoxycarbonylmethyl group containing from 1 to 3 carbon atoms in the alkoxy frequent CLASS="ptx2">

Examples of new derivatives of dimethylpolysiloxane that can be used as an active ingredient an antiseptic for wood according to the present invention, shown in the following table.

In table. 1 used the following abbreviations:

Bz - benzyl

Bu - butyl

Et - ethyl

Hx - hexyl

Me - methyl

Ph - phenyl

Pip - piperidyl

Pn - pencil

Pr - propyl

Among the above compounds, preferred to apply the compounds N 3, 4, 5, 6, 7, 8, 10, 11, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 31, 33, 35, 36, 38, 40, 42, 43, 44, 45, 46, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 69, 70, 71, 72, 75, 80, 81, 82, 83, and 85; and the most preferred are compounds NN 3, 6, 10, 19, 22, 24, 26, 27, 33, 35, 36, 38, 40, 42, 44, 45, 46, 48, 53, 55, 60, 61, 69, 70, 81, 83 and 85.

Compounds according to the abovementioned General formula I can be obtained according to the method, represented either by the following method A or method B.

How A

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Method B

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In the above formulas, R1and R2defined as above. R1represents a C1-C6alkyl group, a C3-C6cycloalkyl group or a benzyl group which may optionally contain 1 or 2 substituent. Connected is SUP>1denotes a hydrogen atom. The compound of formula V is izlesene aniline. X denotes a halogen atom such as chlorine, bromine or iodine, preferably chlorine. X denotes a halogen atom such as chlorine, bromine or iodine, preferably bromine or iodine.

Compounds of the present invention can be obtained by well known methods.

Stage A1 includes obtaining compounds of General formula I by reacting compounds of General formula III with a compound of General formula IV in an inert solvent in the presence of dehydrohalogenating agent.

The compound of formula III used as starting product at this stage, can be obtained by hydrolysis of 2,5-dimethylfuran-3-carboxylate, which can be obtained by condensation of chloroacetone with acetoacetate and subsequent halogenoalkanes.

The compound of the formula IV used as starting product at this stage, is a derivative of aniline, which is commercially available or can be obtained using well known methods.

Examples of inert solvents include, for example, ethers such as ether, isopropyl ether, tetrahydrate, such as dichloromethane, chloroform or carbon tetrachloride; and mixtures of two or more of these solvents; preferably, aromatic hydrocarbons, especially toluene).

The examples used dehydrohalogenating agents include, for example, tertiary amines such as triethylamine, N,N-dimethylaminopyridine or the like, and pyridine. This reaction can be carried out in the presence or in the absence of solvent. In order to smoothly carry out the reaction solvent, the reaction is carried out at a temperature of from 0oC to the boiling point of the used solvent, preferably from room temperature to 100oC. the Time required for the reaction is generally from 30 minutes to 5 hours, preferably from 30 minutes to 2 hours.

Stage B1 includes obtaining compounds having General formula (VI), by reacting compounds having the General formula III with a compound having the General formula V in an inert solvent in the presence of dehydrohalogenating agent.

The compound of formula V used as starting product at this stage, is a derivative of aniline, which is industrially available or can be obtained by , conditions, used on stage A1.

Stage B2 includes obtaining compounds having the General formula Ia by reacting compounds having the General formula VI, with a Grignard reagent having the General formula:

R1MgX,

in an inert solvent in the presence of a catalyst.

Examples of preferred used inert solvents include, for example, ethers such as diethyl ether, isopropyl ether, tetrahydrofuran or dioxane; particularly preferably diethyl ether.

As a particularly preferred catalyst may be used chloride, [1,1'-bis(diphenylphosphino)-ferrocene]palladium (II) (Pd(dppf)Cl2).

The Grignard reagents used in this process are commercially available or can be obtained by reacting magnesium with alkylhalogenide represented by the formula (where R1and X' are defined as above) in accordance with well known methods.

The reaction is usually carried out at a temperature of from 0oC to 50oC, preferably at room temperature. Although the time required for the reaction varies depending on the nature of the solvent and reagent, codeinone, having indicated the General formula I in accordance with the present invention, possess strong antiseptic activity against wood at low concentrations, compared to the activity, show the existing antiseptics for wood. A composition consisting of a combination of the above compound I with a known antiseptic for wood, creates a synergistic effect, and requires a lower concentration than would be expected on the basis of the activity shown by each component separately, so that the composition manifests an effective antiseptic activity against wood at low concentrations. Therefore, new derivatives of dimethylpolysiloxane are extremely effective as antiseptics for wood in low concentration than it solves one of the problems of improving the quality of life.

The following examples illustrate the formation of compounds of the present invention and the preparation of compositions based on them in more detail. These examples may not be construed as limiting the scope of the present invention.

Example 1

3'-Acetylamino-2,5-dimethylfuran-3-carboxanilide

To a solution of 0.50 g of 2,5 dimethyl the drop ice and the resulting mixture was stirred at room temperature for 2.5 hours, then was heated under reflux for 4.5 hours. After the reaction mixture was cooled, it was diluted by adding 10 ml of dichloromethane. The diluted mixture was sequentially washed with 1 N. sodium hydroxide, 1 N. hydrochloric acid and saturated aqueous sodium chloride and dried over sodium sulfate, and then drove the solvent. The residue was purified using column chromatography on silica gel, and the desired fraction was recrystallized from ethyl acetate to obtain 0.51 g of the desired compound in the form of white crystals with a yield of 59.4 per cent.

So pl.: 172,0 - 172,5oC

1H NMR (CDCl3+ DMCO) million-1: 8,4 (1H, usher.), of 7.95 (1H, usher.), 7,88 (1H, m), and 7.4 (1H, m), 7,32 (1H, m), 7,25 (1H, t, J=8 Hz), and 6.25 (1H, s), 3,55 (3H, in), 2.25 (3H, s), of 2.15 (3H, s).

IR (KBr) cm-1: 3306, 1672, 1651, 1086, 781.

Elemental analysis (%): Calculated for C15H16N2O3: C, 66,16; H, OF 5.92; N, 10,29. Found: C, To 66.30; H, 5,98; N, 10,32.

Following a methodology similar to that described above but using the appropriate derivative of aniline instead of 3-acetylaminophenol received the following connections.

Example 2

3'-(N-methylcarbamoyl)-2,5-d-1: 8,5 (1H, usher.), with 8.05 (1H, m), 7,88 (1H, m), 7,52 (1H, m), 7,38 (1H, t, J=8 Hz), 6,8 (1H, usher.), 6.35mm (1H, s), 2,95 (3H, d, J=1.4 Hz), to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3293, 1638, 1581, 1074, 689.

Elemental analysis (%): Calculated for C15H16N2O3: C, 66,16; H, OF 5.92; N, 10,29. Found: C, 66,08; H, 6,20; N, 10,28.

Example 3

3'-(1-Piperidinylcarbonyl)-2.5-dimethylfuran-3-carboxanilide

Output: 50,0% T. pl.: USD 183.0 - to 185.0oC

1H NMR (CDCl3) million-1: to 7.68 (1H, m), 7,55 (2H, m), 7,35 (1H, t, J=8 Hz), and 7.1 (1H, m), x 6.15 (1H, s), 3,7 (2H, usher.), the 3.35 (2H, usher.), to 2.55 (3H, in), 2.25 (3H, s), 2,75 - 1,4 (6H, m).

IR (KBr) cm-1: 3302, 1663, 1615, 1065, 808.

Elemental analysis (%): Calculated for C19H22N2O3: C, 69,92; H, 6,79; N, 8,58. Found: C, 69,52; H, To 6.88; N, 8,48.

Example 4

3'-(N-phenylcarbamoyl)-2.5-dimethylfuran-3-carboxanilide

Output: 53.5% of

T. pl.: 182,5 - 184,0oC

1H NMR (CDCl3+ DMCO) million-1: 8,48 (1H, usher.), of 8.2 (1H, usher.), 8,1 (1H, s), 7,95 (1H, m), and 7.7 (2H, d, J = 8 Hz), the 7.65 (1H, d, J=8 Hz), was 7.45 (1H, t, J=8 Hz), 7,35 (2H, t, J=8 Hz), to 7.15 (1H, t, J=8 Hz), 6,28 (1H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3282, 1646, 1080, 755, 691

Elemental analysis (%): Calculated for C20H18N2O3: C, 71,84; H, 5,43; N, SCORED 8.38. Found: C, 71,87; H, 5,64; N, 8.34 Per.

Example 5

3'-Tert-butoxy the SUB>) million-1: with 8.05 (1H, m), 7,88 (1H, m), of 7.75 (1H, m), and 7.4 (1H, t, J=8 Hz), 7,35 (1H, usher.), 6,1 (1H, s) to 2.55 (3H, in), 2.25 (3H, s), of 1.65 (9H, s).

IR (KBr) cm-1: 3362, 1687, 1672, 1067, 757.

Elemental analysis (%): Calculated for C18H21HO4: C, 68,55; H, OF 6.71; N, OF 4.44. Found: C, 68,04; H; 7,00; N, 4,40.

Example 6

3 Methoxycarbonyl-2,5-dimethylfuran-3-carboxanilide

Output: 77,1%

T. pl. 104,0 - to 106.0oC

1H NMR (CDCl3) million-1: with 8.05 (1H, m), 7,98 (1H, m), and 7.8 (1H, m), 7,42 (1H, t, J=8 Hz), 7,38 (1H, usher.), 6,1 (1H, s) to 3.92 (3H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3437, 1704, 1675, 1070, 759.

Elemental analysis (%): Calculated for C15H15NO4: C, 65,92; H, OF 5.53; N, 5,13. Found: C, 66,02; H, The Ceiling Of 5.60; N, 5.08 To.

Example 7

3'-Benzoyl-2,5-dimethylfuran-3-carboxanilide

Output: 69,1%

T. pl.: 137,0 - 139,0oC

1H NMR (CDCl3) million-1: with 8.05 (1H, m), a 7.85 - in 7.7 (3H, m), and 7.6 (1H, m), 7,55 - to 7.35 (5H, m), 6,1 (1H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3386, 1672, 1647, 1069, 707.

Elemental analysis (%): Calculated for C20H17NO3: C, 75,22; H, LOWER THAN THE 5.37; N, 4,39. Found: C, 75,38; H, 5,43; N, To 4.38.

Example 8

3'-Benzoylamine 2.5-dimethylfuran-3-carboxanilide

Output:46,0%

T. pl.: 194,5 - 195,0oC

1H NMR (CDCl3+ DMCO) million-1: 8,7 (1H,SUP>: 3283, 1642, 1074, 791, 705

Elemental analysis (%) : Calculated for C20H18N1O3: C, 71,84; H, 5,43; N, SCORED 8.38. Found: C, 71,96; H, Of 5.53; N, 8,28.

Example 9

3'-Valeriano-2,5-dimethylfuran-3-carboxanilide

Yield: 70.3% of

T. pl.: 104,0 - 105,0oC

1H NMR (CDCl3) million-1: 7,9 (1H, usher.), 7,45 to 7.1 (5H, m), 6,1 (1H, s) to 2.55 (3H, s) to 2.35 (2H, t, J=7 Hz), of 2.25 (3H, s), 1,7 (2H, m), 1,4 (2H, m) of 0.95 (1H, t, J=7 Hz).

IR (KBr) cm-1: 3250, 1660, 1644, 1074, 781

Elemental analysis (%): Calculated for C18H22N2O3: C, 68,77; H, 7,05; N, 8,91. Found: C, 68,73; H, 7,17; N, 8,90.

Example 10

3'-Cyclohexylcarbodiimide-2,5-dimethylfuran-3-carboxanilide

Output: 45,1%

So pl.: 212,5 - 213,0oC

1H NMR (CDCl3+ DMCO) million-1: a 7.92 (1H, usher.), 7,88 (1H, usher.), 7,45 - to 7.35 (2H, m), 7,25 (1H, t, J = 8 Hz), to 6.22 (1H, s) to 2.55 (3H, in), 2.25 (3H, s), 2,25 - 2,2 (1H, m) , a 2.0 a 1.2 (10H, m).

IR (KBr) cm-1: 3238, 1651, 1639, 1076, 781.

Elemental analysis (%): Calculated for C20H24N2O3: C, 70,57; H, 7,11; N, 8,23. Found: C, 70,56; H, 7,26; N, 8,16.

Example 11

2.5-Dimethylfuran-3-carboxy(3-methoxyethylamine)

Output: 73,3%

So pl.: 102,5 - 103,5oC

1H NMR (CDCl3) million-1: of 7.55 (1H, m), 7,52 (1H, d, J = 8 Hz), 7,32 (1H, t, J = 8 Hz), 7,32 (1H, usher.), of 6.9 (1H, the elemental analysis (%): Calculated for C15H17NO3: C, 69,48; H, IS 6.61; N, 5.40 TO. Found: C, 69,22; H, 7,02; N, Lower Than The 5.37.

Example 12

3'-Ethoxyethyl-2,5-dimethylfuran-3-carboxanilide

Output: 64,4%

So pl.: 85,0 - 85,5oC

1H NMR (CDCl3) million-1: the 7.65 at 7.55 (2H, m), 7,38 (1H, t, J = 8 Hz), 7,35 (1H, usher.), to 7.15 (1H, d, J = 8 Hz), x 6.15 (1H, s) 4,55 (2H, s) to 3.58 (2H, q, J = 8 Hz), to 2.55 (3H, in), 2.25 (3H, s), 1,3 (3H, t, J = 8 Hz).

IR (KBr) cm-1: 3279, 1646, 1115, 785.

Elemental analysis (%): Calculated for C16H19NO3: C, 70,31; H, 7,01; N, 5,12. Found: C, 70,14; H, 7,27; N Is 5.06.

Example 13

3'-Isopropylaminomethyl-2,5-dimethylfuran-3-carboxanilide

Yield: 92.7% of

So pl.: 68,0 - 69,5oC

1H NMR (CDCl3) million-1: of 7.55 (1H, d, J = 8 Hz), and 7.5 (1H, m), and 7.3 (1H, t, J = 8 Hz), and 7.3 (1H, usher.), for 7.12 (1H, d, J = 8 Hz) and 6.1 (1H, s), and 4.5 (2H, s), and 3.7 (1H, m) to 2.55 (3H, in), 2.25 (3H, s), 1,25 (6H, d, J = 7 Hz).

IR (liquid film) cm-1: 3321, 1651, 1072, 785.

Elemental analysis (%): Calculated for C17H21NO3: C 71,06; H, 7,37; N, 4,87. Found: C, 70,35; H, 7,14; N, 4,91.

Example 14

3'-(4-Methoxybenzyl)-2.5-dimethylfuran-3-carboxanilide

Yield: 86.8% of the

So pl.: 100,0 - 102,5oC

1H NMR (CDCl3) million-1: was 7.45 (1H, m), 7,35 (1H, m), 7,25 (1H, t, J = 8 Hz), 7,25 (1H, usher.), and 7.1 (2H, d, J = 8 Hz), 6,92 (1H, d, J = 8 Hz), 6,88 to 6.75 (1H, m), PC 6.82 (2H, dementy analysis (%): Calculated for C21H21NO3: C, 75,20; H, OF 6.31; N, 4,18. Found: C, To 75.28; H, 6,32; N, 4,21.

Example 15

3'-(2-Methoxycarbonylbenzyl)-2.5-dimethylfuran-3-carboxanilide

Yield: 63.3% of

So pl.: 159,5 - 161,5oC

1H NMR (CDCl3) million-1: of 7.82 (1H, m), and 7.7 (1H, d, J = 15 Hz), 7,58 (1H, m), 7,38 (1H, usher.), to 7.35 (1H, t, J = 8 Hz), 7,28 (1H, m), 6.48 in (1H, d, J = 15 Hz), 6,12 (1H, s), 3,82 (3H, s) to 2.55 (3H, in), 2.25 (3H, s)

IR (KBr) cm-1: 3387, 1685, 1670, 1068, 800.

Elemental analysis (%): Calculated for C17H17NO4: C, 68,22; H, 5,72; N, 4,68. Found: C 67,55; H, 5,64; N, 4,62.

Example 16

3'-Phenyl-2,5-dimethylfuran-3-carboxanilide

Output: 50,0%

So pl.: 90,0 - 92,0oC

1H NMR (CDCl3) million-1: of 7.82 (1H, s), and 7.6 (2H, d, J = 8 Hz), 7,55 (1H, d, J = 8 Hz), 6.48 in - 6,3 (6H, m), 6,12 (1H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3367, 1646, 1074, 755.

Elemental analysis (%): Calculated for C19H17NO2: C, 78,33; H, 5,88; N, 4,81. Found: C, 78,17; H; 6,00; N, 4.72 In.

Example 17

3'-Neopentylene-2,5-dimethylfuran-3-carboxanilide

Output: 50,0%

So pl.: 95,5 - 97,0oC

1H NMR (CDCl3) million-1: of 7.48 (2H, m), 7,32 (1H, t, J = 8 Hz), and 7.3 (1H, user. ), 7,12 (1H, d, J = 8 Hz), to 4.52 (2H, s), of 3.12 (2H, s) to 2.55 (3H, in), 2.25 (3H, s) of 0.95 (9H, s).

IR (KBr) cm-1: 3324, 1646, 1091, 700.

Element the EP 18

3'-Isopropenyl-2,5-dimethylfuran-3-carboxanilide

Output: 50,0%

So pl.: 71,0 - 72,0oC

1H NMR (CDCL3) million-1: the 7.65 (1H, m), and 7.5 (1H, m), and 7.3 (1H, usher.), of 7.3 (1H, t, J=8 Hz), 7,22 (1H, m), 6,12 (1H, s), 5,4 (1H, s), 5,1 (1H, s), 2,6 (3H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3275, 1641, 1580, 1078, 790.

Elemental analysis (%): Calculated for C16H17NO2: C, 75,27; H, OF 6.71; N, 5,49. Found: C, 75,29; H, To 6.88; N, 5,48.

Example 19

3'-Ethinyl-2,5-dimethylfuran-3-carboxanilide

Output: 50,0%

So pl.: 83,0 - 84,0oC

1H NMR (CDCl3) million-1: 7,7 (1H, m), and 7.6 (1H, m), 7,32 to 7.2 (3H, m), 6,1 (1H, s), 3,05 (1H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3245, 1644, 1079, 796.

Elemental analysis (%): Calculated for C15H13NO: C, 75,30; H, OF 5.48; N, 5,85. Found: C, 75,50; H, 5,46; N, 5,96.

Example 20

3'-Ethyl-2,5-dimethylfuran-3-carboxanilide

Output: 91,0%

So pl.: level 113.0 - 115,0oC

Mass spectrometry (m/z: 243 (M+), 123,94

1H NMR (CDCL3) million-1: 7,47 - to 6.95 (4H, m), 6,1 (1H, s) to 2.66 (3H, HF), 2,60 (3H, s) to 2.29 (3H, S), 1,25 (3H, t).

Example 21

3'-Isopropyl-2,5-dimethylfuran-3-carboxanilide

Output: 84,0%

So pl.: 79 - 80oC

Mass spectrometry (m/z): 257 (M+), 149,135

1H NMR (CDCl3) million-1: -3-carboxanilide

Output: an 85.2%

So pl.: USD 128.0 - 131,0oC

Mass spectrometry (m/z): 271 (M+), 242,228

1H NMR (CDCl3) million-1: 7,28 for 7.12 (3H, m), PC 6.82 (1H, usher.), 6,16 (1H, s), 2.63 in (4H, HF), 2,58 (3H, s), 2,31 (3H, s) of 1.20 (6H, t).

Example 23

3'-Hexyl-2,5-dimethylfuran-3-carboxanilide

(Stage 1) To a solution of 3.95 g of 2,5-dimethylfuran-3-carbonylchloride in 60 ml of chloromethane added to 3.45 ml of triethylamine and 2,99 ml m-itanyone under ice cooling and the resulting mixture was stirred at room temperature.

(Stage 1) To a solution of 3.95 g of 2,5-dimethylfuran-3-carbonylchloride in 60 ml of chloromethane added to 3.45 ml of triethylamine and 2,99 ml m-itanyone under ice cooling, and the resulting mixture was stirred at room temperature for 6.5 hours. After the reaction mixture was cooled, it was diluted by adding 50 ml of dichloromethane. The diluted mixture was sequentially washed with 1 N. sodium hydroxide, 1 N. hydrochloric acid and saturated aqueous sodium chloride and dried over sodium sulfate, and then drove the solvent. The residue was subjected to purification using column chromatography on silica gel with receipt of 7.64 g of 2,5-dimethylfuran-3-carboxy(3-loganlea) in the form of pale yellow crystals, which is suitable for obavljale of 29.3 mg of chloride, [1,1'-bis(diphenylphosphino)ferrocene] palladium II and 11 ml of 1 M hexylaniline, obtained from hexylboronic and magnesium, divided into 6 equal parts, and the resulting mixture was stirred at room temperature for 47 hours. After adding 2 N. hydrochloric acid to the reaction mixture, the catalyst was filtered and the filtrate was extracted with diethyl ether. The extract was sequentially washed with an aqueous solution of sodium bicarbonate and saturated aqueous sodium chloride and dried over sodium sulfate. After removal of the solvent the residue was purified using column chromatography on silica gel, and then on a column filled with phase D-ODS-5, YMC, obtaining 316 mg of the desired compound in the form of white crystals, which corresponds to a yield of 52.8%.

So pl.: 71,5 - 72,0oC

1H NMR (CDCl3) million-1: was 7.45 (1H, m), 7,35 (1H, m), 7,25 (1H, usher.), 7,22 (1H, t, J=8 Hz), to 6.95 (1H, d, J=8 Hz) and 6.1 (1H, s), 2,65 - 2,5 (2H, m) to 2.55 (3H, in), 2.25 (3H, s), 1,7 - 1,5 (2H, m), 1,4 - 1,2 (6H, m) of 0.85 (3H, t, J=7 Hz).

IR (KBr) cm-1: 3310, 1643, 1077, 788.

Elemental analysis (%): Calculated for C19H25NO2: C, 76,22; H, 8,42; N, 4,68. Found: C, 76,15; H, 8,54; N, 4,55.

Following a methodology similar to that described above but using the appropriate Grignard reagent instead of hexylaniline received the following connections.

Example (CDCL3) million-1: was 7.45 (1H, m), 7,35 (1H, m), 7,25 (1H, usher.), 7,22 (1H, t, J=8 Hz), to 6.95 (1H, d, J=8 Hz) and 6.1 (1H, s), 2,65 is 2.55 (2H, m) to 2.55 (3H, in), 2.25 (3H, s), 1,6 (2H, m) of 1.35 (2H, m) to 0.92 (1H, t, J=7 Hz).

IR (KBr) cm-1: 3285, 1646, 1075, 702.

Elemental analysis (%): Calculated for C17H21NO2: C, 75,25; H, 7,80; N, 5,16. Found: C, 75,13; H, 7,87; N, 5,13.

Example 25

3'-sec-butyl-2,5-dimethylfuran-3-carboxanilide

Output: 38,1%.

So pl.: 80,0 - 81,0oC

1H NMR (CDCl3) million-1: 7,4 (1H, m), 7,38 (1H, m), 7,25( 1H, usher.), 7,22 (1H, t, J=8 Hz), to 6.95 (1H, d, J=8 Hz) and 6.1 (1H, s), 2,65-2,5 (1H, m) to 2.55 (3H, in), 2.25 (3H, s), 1,68-1,5 (1H, m), 1,25 (3H, d, J=7 Hz), of 0.85 (3H, t, J=7 Hz).

IR (KBr) cm-1: 3255, 1647, 1078, 791.

Elemental analysis (%): Calculated for C17H21NO2: C, 75,25; H, 7,80; N, 5,16. Found: C, 75,19; H, To 7.68; N, 5,14.

Example 26

3'-Pentyl-2,5-dimethylfuran-3-carboxanilide

Output: 18,3%

So pl.: 97,0 - 97,5oC

1H NMR (CDCl3+ DMCO) million-1: was 7.45 (1H, m), 7,35 (1H, m), 7,28 (1H, user. ), to 7.25 (1H, t, J=8 Hz), to 6.95 (1H, d, J=8 Hz) and 6.1 (1H, s), 2,65-2,5 (2H, m) to 2.55 (3H, in), 2.25 (3H, s), 1,7-1,5 (2H, m), 1,4-1,2 (4H, m) to 0.88 (3H, t, J=7 Hz).

IR (KBr) cm-1: 3304, 1644, 1077, 710.

Elemental analysis (%): Calculated for C18H23NO2: C, 75,76; H, 8,12; N, 4,91. Found: C, 75,77; H, 8,18; N Is 5.06.

Example 27
>H NMR (CDCl3) million-1: of 7.48 (1H, m), 7,35 (1H, m), 7,28 (1H, usher.), of 7.25 (1H, t, J= 8 Hz), 6,98 (1H, d, J=8 Hz) and 6.1 (1H, s) to 2.55 (3H, s), 2,55 at 2.45 (1H, m), of 2.25 (3H, s) 1,95 by 1.68 (5H, m), 1,55-1,15 (5H, m).

IR (KBr) cm-1: 3324, 1646, 1230, 1074, 791.

Elemental analysis (%): Calculated for C19H23NO2: C, 76,74; H, 7,80; N, 4,71. Found: C, 76,62; H, 7,78; N, 4,67.

Example 28

3'-Cyclopentyl-2,5-dimethylfuran-3-carboxanilide

Output: 35,9%.

So pl.: 92,0 - 93,0oC

1H NMR (CDCl3) million-1: was 7.45 (1H, m), 7,35 (1H, m), 7,25 (1H, usher.), 7,22 (1H, t, J=8 Hz), 7,00 (1H, d, J=8 Hz) and 6.1 (1H, s), is 3.08 and 2.9 (1H, m) to 2.55 (3H, in), 2.25 (3H, s), 2,15-of 1.95 (2H, m), 1,9-1,5 (6H, m).

IR (KBr) cm-1: 3322, 1647, 1232, 1076, 700.

Elemental analysis (%): Calculated for C18H21NO2: C, 76,30; H, 7,47; N, 4,94. Found: C, 76,21; H, 7,56; N Is 4.93.

Example 29

3'-Benzyl-2,5-dimethylfuran-3-carboxanilide

Output: 59,8%.

So pl.: 123,0 - 125,0oC

1H NMR (CDCl3million-1: was 7.45 (1H, m), 7,38 (1H, m), 7,35-to 7.15 (7H, m), to 6.95 (1H, d, J=8 Hz), 3,98 (2H, s) to 2.55 (3H, in), 2.25 (3H, s).

IR (KBr) cm-1: 3314, 1640, 1078, 777, 701.

Elemental analysis (%): Calculated for C21H19NO2: C 78,66; H, 6,27; N 4,59. Found: C, 77,76; H, 6,28; N, 4,55.

Reference example 1

Ethyl(2,5-dimethylfuran-3-carboxylate)

referred to as DMF) was added dropwise a solution of 6.5 ml of ethylacetoacetate in 5 ml of DMF under stirring and cooling with ice, and to this mixture was added dropwise to 5.7 ml chloroacetone under stirring and cooling with ice. After stirring at room temperature for 3 hours, the reaction mixture was poured into water and extraction was performed from the aqueous mixture with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure the residue was distilled in vacuum, obtaining 8,01 g of ethyl ( - acetonitrile) with So pl. 105oC/266,6 PA, which corresponds to a yield of 86%.

To the solution thus obtained complex ester in 20 ml ethanol was added 2 g of p-toluensulfonate acid, and the resulting mixture was heated under reflux for 2 hours. The reaction mixture was allowed to cool to room temperature and kept off the solvent under reduced pressure. The residue was dissolved in ethyl acetate and the solution washed with saturated aqueous sodium chloride, then dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure the residue was purified using column chromatography on silica gel using as eluent a mixture of n-hexane and ethyl acetate in a ratio of 10:Mer 2

2.5-Dimethylfuran-3-carboxylic acid

A mixture of 3.2 g of ethyl(2,5-dimethylfuran-3-carboxylate), 35 ml of ethanol and 20 ml of 2 n sodium hydroxide was stirred at room temperature for 1.5 hours, then was heated under reflux for one hour. After the reaction mixture was allowed to cool to room temperature, it was evaporated under reduced pressure. The residue was dissolved in water and acidified with diluted sulfuric acid. Precipitated precipitated crystals were collected by filtration, washed with water and dried with receipt of 2.27 g of 2,5-dimethylfuran-3-carboxylic acid, which corresponds to a yield of 85%.

The compound having the General formula I mentioned above, and the composition containing compound I as active component, which relates to the present invention can be applied by mixing with the carrier or, if necessary, other additives, and subsequent preparation of commonly used compositions, such as oil solution, emulsibility concentrate, solubilizer, pastes, wettable powder, flowable composition, the dry flowable composition, aerosol and paint, and then the composition can be used according to known methods of processing wood antisepti and strengthen protective effect on the wood, can be mentioned cationogenic, anionic and nonionic surfactants, various high molecular weight polymers such as methyl cellulose and vinyl acetate polymer, and water additives, such as silicone oil and paraffin. Needless to say that the combination with other antiseptics for wood, fungicides and bactericides, including organic iodine compounds, such as Sanplas, IF-1000 and Troysan, azole compounds such as Propiconazole and Tebuconazole, Thiabendazole, Dichlofluanid (dichlofluanid), and connections, which represents a Quaternary ammonium salt; with insecticides, including pyrethroids, such as Permethrin (permethrin), Etofenprox, Cypermethrin (cypermethrin), Silaneophen, Tralomethrin, organophosphorus compounds such as Chloropyrifos, Phoxin and Propetamphos, and Imidacroprid; and with a synergistic effect means, such as bis-(2,3,3,3-tetrafluoropropyl)-ether. When combined in this way can be expected to be superior effect. Almost in the application, although the content of the compounds of the present invention may vary within wide limits depending on the composition or from an object, usually it can be suitable for use in the range from 0.1 to 95 prebody wood: for example, coating, spraying, treatment by dipping, mixing, impregnation, or processing by simultaneously mixing with glue.

Some examples of compositions with the compounds of the present invention will be shown below, in respect of which there is no need to say that the ratio in which the components are combined, and the type of additives can vary widely (data below descriptions "part" in all cases means "part by weight").

Examples of compositions with antiseptics for wood

Example compositions 1 Emulsibility concentrate

Twenty parts of compound 1 was dissolved in 70 parts of xylene, and then added 10 parts polyoxyethyleneglycol ether and mixed sufficiently, getting emulsibility concentrate.

Thus obtained emulsibility the concentrate is diluted with a suitable amount of water immediately before use and can be used for wood materials that must be processed by coating, dipping or spraying, and, in addition, may be used by mixing with adhesives that are used for plywood, chipboard and solid dragoslavele the pits kerosene, getting oil solution.

Thus obtained oil solution can be used for wood materials that must be processed by spraying, coating, dipping or impregnation.

An example of the composition 3. Composition for coating

Ten parts of compound 1, 20 parts of barium dust, 10 parts of vinyl polymer, 25 parts of pine resin and 35 parts of xylene were mixed to a homogeneous state, receiving a composition for coating.

Example of composition 4. Wettable powder

Twelve parts of compound 3, 56 parts of clay, 3 parts sulfonate sodium - lauric alcohol and 1 part of polyvinyl alcohol were mixed until smooth in a blender, and then were crushed by using a hammer mill, receiving a wettable powder.

Examples of tests for the protection of wood

The effectiveness of antiseptics for wood according to the present invention will be specifically explained using the following examples.

(1) According to the test method for the protection of timber described in industry standards of Japan [Japan Industrial standards JIS A-9201 (1991)], each of the tested compounds were dissolved to a certain end is dried in the air. The test for resistance to weathering, in which one cycle of treatment consisted of mixing in water for 8 hours and then heated for 16 hours at 60oC, was repeated 10 times. The test material was placed on flora Serpula lacrymans, which was previously cultivated in the medium of quartz sand (malt extract 2%, glucose 1%, peptone 0.3% yeast 0,2%), and were subjected to accelerated decomposition at 20oC for 12 weeks. From the difference between the dry weight of the test product before the test and its dry weight after the test received the degree of weight loss. The results are shown in table. 2. The test was performed by using 9 samples for each variant test conditions, and the values shown in the table. 2 are the average values computed from the data for 9 samples.

The control compound 1: 4-chlorophenyl-3-iodopropargyl

The product of the company Nagase Co., Ltd.: IF-1000

According to the presented data, the compounds having General formula (I), in a noticeable extent prevent the rotting of wood samples caused derevorazrushayushimi fungi.

(2) Each of the solutions of the compounds of the present invention in methanol with a concentration of 0.1% weight to about nom pressure, and then air-dried. The test for resistance to weathering, in which one cycle of treatment consisted of washing (flow rate of about 2 liters per minute) water for 5 hours, and then heated for 19 hours at 60oC, was repeated twice. After sterilization, dry air received the samples.

The test material was placed on flora Coriolus Versicolor, which is a demoralizing lignin fungus, and Tyromyces palustris, which is a demoralizing cellulose fungus, and that both are installed fungi species for samples on preventing the effects of antiseptics for wood. Both fungi were pre-grown on medium of agar (malt extract 2%, glucose 1%, peptone 0.5 percent). After the wood samples were subjected to accelerated destruction at the 26oC for 3 weeks, determined the effectiveness of the degree of hyphal growth on tested material and the presence or absence of reduced maximum strength crush strength. The results are shown in table. 3.

The effectiveness of protection of the wood was assessed on the following criteria.

+ : The test material was not observed hyphal growth, and did not find any differences with povrezhdeniya small growth of hyphae or found a small decrease in maximum strength crush strength.

- : The test material was observed the growth of hyphae or were found a clear decrease of the maximum crushing strength.

- : The test material was observed the growth of hyphae or were found a clear decrease of the maximum crushing strength.

The control compound 2: 3-Bromo-2,3-diid-2-propylethylene

The product of the company Sankyo Co., LTD.: Sanplas

When you want to apply the composition of the present invention, the ratio, which is the combination may be appropriately selected depending on the type of wood and type of wood material, which should be treated with a preservative for wood, or processing method (for example, coating, immersion, spraying, impregnation, mixing or blending together with glue). Usually the ratio, which is a combination of dimethylpolysiloxane and any other antiseptics for wood, can range from 240:1 to 1:35, preferably from 30:1 to 1:10, and more preferably from 5:1 to 1:5.

The content of the composition according to the present invention may vary within a wide range depending on the composition. In General, the content in the composition may range from 0.1 to 95%, predpochtitelen shown below, in respect of which there is no need to say that the ratio in which the components are combined, and the type of additives can vary within wide limits.

Examples of compositions with protective compounds for wood

Example compositions 1 Emulsibility concentrate

Ten parts of compound 1 was dissolved in 30 parts of drug Sanplas and 50 parts of xylene was then added 10 parts polyoxyethyleneglycol ether and mixed sufficiently, getting emulsibility concentrate.

Thus obtained emulsibility the concentrate was diluted with a suitable amount of water immediately before use and can be used for wood materials that must be processed by coating, dipping or spraying, and, in addition, may be used by mixing with adhesives that are used for plywood, chipboard and solid fiberboard.

Example composition 2 Oil solution

Two connection parts 2 and 1 part of drug troysan was dissolved in 96 parts of kerosene, getting oil solution.

An example of the composition 3 Wettable powder

Fifteen parts of compound 3, 25 parts pre is ivali until smooth in a blender, and then were crushed by using a hammer mill, receiving a wettable powder.

The protective effect of compounds for impregnation of wood according to the present invention will be specifically explained using the following examples.

Examples of tests of protective compounds for wood

A sample of minimum inhibitory concentration using the agar dilution.

In accordance with the method of dilution agar, sterilized medium (agar medium based on potato dextrose; powder potato extract 0.4%, glucose 2%, agar 1.5%), while prepared with the content of certain concentrations of the test samples was inoculable flora (about 4 mm in diameter) wood-destroying fungi, Coriolus Versicolor and Tyromyces palustris, which was pre-cultivated on the same medium type. After culturing at 25oC for 5 days and observed for growth of hyphae to determine the minimum inhibitory concentration.

Determining whether any enhanced activity or not, described in C. Kull et al., Applied Microbiology 9, 538 - 541 (1961). Tests were conducted according to the generally used method.

In table. 4 to 6 and figures 1 (a) - (e) shows the results, pnie, as described, was carried out for the connection 2. The results are shown in table. 7 - 9 and figures 2 (a) - (e).

Each of the curves of minimum inhibitory concentration, shown in figures 1 and 2, lies below the diagonal line shown by the dotted line.

These data show that the derived dimethylpolysiloxane enhances the action of each of the drugs Sanplas, Troysan and IF-1000 in combination with them.

1. Derivatives dimethylpolysiloxane General formula I

< / BR>
where R1and R2- same or different, each represents a hydrogen atom, a C2-C6-alkyl, C3-C6-cycloalkyl, C3-C6alkenyl, C2-C6-quinil, C1-C3-halogenated, C2-C6-alkoxygroup, C1-C6-alkoxy-C1-C6-alkyl, substituted amide group, a C1-C6-alkoxycarbonyl, benzoyloxy group which may contain one or two Deputy, benzoylamino, which may contain one or two Deputy, C2-C6-alkanolamines, C3-C6- cycloalkylcarbonyl, benzyl group, which may contain one or two substituent, phenyl group which may SDA, provided that (1) R1and R2at the same time are not hydrogen atoms, (2) one of R1and R2is not unsubstituted phenyl group when the other one represents a hydrogen atom, (3) one of R1and R2in anthopology is not an aniline ring, C2-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkoxygroup when the other one represents a hydrogen atom.

2. Protective composition for wood, containing the active ingredient, characterized in that as the active ingredient it contains an effective amount of a derivative dimethylpolysiloxane under item 1.

3. The way to protect the wood by applying the composition containing the active ingredient, characterized in that the applied composition comprising an effective amount of a derivative dimethylpolysiloxane General formula I

< / BR>
where R1and R2- same or different, each represents a hydrogen atom, a C2-C6-alkyl, C3-C6-cycloalkyl, C3-C6alkenyl, C2-C6-quinil, C1-C3-halogenated, C2-C6-alkoxygroup, C1-C6-alkoxy-C12-C6-alkanolamines, C3-C6-cycloalkylcarbonyl, benzyl group, which may contain one or two substituent, phenyl group, which may contain one or two Deputy, or C1-C6-alkoxycarbonyl-C2-C6-alkynylamino group, provided that R1and R2are not simultaneously represent hydrogen atoms.

4. Protective composition for wood, containing the active ingredient, characterized in that as the active ingredient it contains a mixture of at least one of the derived dimethylpolysiloxane specified in paragraph 3, and at least one compound selected from 3-bromo-2,3-dead-2 - propylethylene, 3-iodine-2-propynylbutylcarbamate and 4-chloro-phenyl-3 - iodopropargyl taken in effective amounts.

 

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