2-(carboxy-h-alkyl)ethyltriphenyl phosphonium bromides, having bactericidal and fungicidal activity

FIELD: chemistry.

SUBSTANCE: present invention relates to 2-(carboxy-n-alkyl)ethyltriphenyl phosphonium bromides of general formula I, having bactericidal and fungicidal activity, heat resistance and surfactant resistance, which can be used in veterinary, medicine and agriculture , where R = n-C10H21 n-C12H25, n-C14H29, n-C16H33, n-C18H37.

EFFECT: obtaining novel biologically active compounds.

1 cl, 6 ex, 1 tbl

 

The invention relates to the field of organophosphorus chemistry, in particular chemical compounds, namely 2-carboxy-n-alkyl)ethyltriphenylphosphonium bromides of General formula I:

where R=n-C10H21n-C12H25; n14H29; n16H33n-C18H37,

having high bactericidal and fungicidal activity at low concentrations, which can find application in the field of veterinary medicine and agriculture as drugs and disinfectants.

Known analogue of the claimed compounds on purpose - the active ingredient of many domestic and foreign (France, Germany, the Netherlands) antibacterial, antiseptic drugs - benzalconi chloride (Benzalkonium chloride), which is a chloride alkyldimethyl(phenylmethyl)ammonium [Jansson P.M. Medical encyclopedic dictionary (Collins), Moscow: Astrel, 2006, 1375 S.].

The disadvantage of this drug is its low thermal stability up to 100°C, as well as all of ammonium salts, which when heated decompose the source amines and lose their therapeutic activity. In connection with this difficult and sterilization of these drugs. In addition, all products containing benzalconi chloride, dissolved soap, as stated in the instructions for their application is [Burbelo A.T., Shabrov A.V. Modern medicines. - M.: OLMA Media Group, 2007, - S].

Known structural analogs of compounds (I) - alkylated carboxylated fostamatinib with lower halide alkilani

where R1=CH3C2H5; n3H7; from.-With3H7; n4H9; from.-With4H9; from.-With5H11; Hlg=Cl, Br, I

the method of obtaining of which lies in the interaction of triphenylmethylchloride with lower halide alkilani environment chloroform or benzene at room temperature. However, in this method it is impossible to obtain alkylated betaines with higher halide alkilani, so as to obtain the required temperature (between 50°C and above, and an excess of alkyl halide). In addition, these compounds do not possess fungicidal and bactericidal activity, which is probably due to the fact that salts of Quaternary phosphonium a lower halide alkilani not show biological activity [van Weser. Phosphorus and its compounds. M: Foreign literature. 1962. S].

Known phosphonium salts of long alkyl radicals exhibiting antibacterial, antifungal and antimicrobial properties [Galkin I., Todri E.V., bakhtiyarova J.V., Egorov, S., Galkin V.I. Synthesis, structure and research biologists who eskay activity of phosphonium salts / collection: Pharmacology and toxicology of organophosphorus compounds and other biologically active substances. - Kazan, 2008. - P.23; Pat. JP 2002308713, publ. 23.10.2002; Pat. JP 2005060332, publ. 10.03.2005; Pat. JP 2000316701, publ. 21.11.2003]. However, all these compounds in aqueous solutions in most cases break down into a tertiary phosphine oxide and hydrocarbon part. Thus, these compounds are unstable at temperatures close to the temperatures of sterilization, which significantly limits their wide application in the manufacture of drugs. In addition, they have a serious drawback - decompose conventional surfactants. This line of decomposition reactions was established in 1857 by Kagura and Hoffmann [Purdila D., Vulcano R. Chemistry of organic compounds of phosphorus. // M.: Chemistry, 1972. S-255].

Investigated by the applicant prior art as of the date of filing of application materials did not reveal the presence in the prior art the closest analogs as on the composition and achieved the claimed technical solution technical(it) result(s).

Thus, the objective of the claimed technical solution is the synthesis of new stable, not subject to hydrolysis, fofanah compounds, alkyl betaines (I)having as bactericidal, fungicidal activity at low concentrations, resistant to surfactants that extends the range of known means specified destination.

The technical result is the new stable is drugs - 2-(carboxy-n-alkyl)-ethyltriphenylphosphonium bromides of the formula (I)having bactericidal and fungicidal activity at low concentrations, resistant to surfactants.

The technical result is achieved by obtaining 2-(carboxy-n-alkyl)-ethyltriphenylphosphonium bromides of the formula (I)have antibacterial and antifungal properties at low concentrations, resistant to surfactants.

The claimed compounds obtained by the interaction of triphenylmethylchloride (II) when heated for 5-7 hours with the highest bromide by alkilani (III) at a molar ratio of 1:2 according to the scheme:

where R=n-C10H21n-C12H25n-C14H29the h16H33n-C18H37.

Source carboxylated fosphenytoin (II) is available, the connection can easily be derived from triphenylphosphine and acrylic acid, the method of its synthesis are described in the paper: [Vigalchin, Yevpatoria, Naalehu, Evelkin etc. // Joh. 2002, T, Issue 3, S-411]. Higher bromide alkali formula (III) is cost-effective connection.

The method is illustrated by the following examples, but is not limited to them.

Example 1. The method of obtaining 2-(carboxymethyl)ethyltriphenylphosphonium bromide:

To a solution 3,34 g (0,01 mol) of triphenylmethylchloride in 50 ml is hloroform added a solution of 4.42 g (0,02 mol) of n-decembered. The reaction mixture is heated to 50°C and heat under reflux for 5 hours, then cooled, the product wikidot diethyl ether. The precipitate was separated, washed with ether and dried. Output 4,32 g (77.8%), oil.

The infrared spectrum, cm-1: 1720 (O-C=O)

C31H40O2PBr

Calculated, %: C 67,03; N 7,21; P 5,59

Found, %: C 66.93; H EUR 7.57; P 6,01

An NMR spectrum31P, chloroform, δ ppm 25,58

Example 2. Synthesis of 2-(carboxymethyl)ethyltriphenylphosphonium bromide:

To a solution 3,34 g (0,01 mol) of triphenylmethylchloride in 50 ml of chloroform is added a solution to 4.98 g (0,02 mol) of n-decembered. The reaction mixture is warm during boiling solvent (61.2°C.) under reflux for 6 hours, then cooled, the product wikidot diethyl ether. The precipitate was separated, washed with ether and dried. The output of 4.67 g (80.1%), oil.

The infrared spectrum, cm-1: 1720 (C=O)

C33H44O2PBr

Calculated, %: C 67,92; N. Of 7.55; P 5,32

Found, %: C 67.41; H 8,01; P 5,55

An NMR spectrum31P, chloroform, δ ppm 24,62

Example 3. Synthesis of 2-(carboxytetramethyl)ethyltriphenylphosphonium bromide:

To a solution 3,34 g (0,01 mol) of triphenylmethylchloride in 50 ml of benzene is added a solution 5,54 g (0,02 mol) of n-tetradecanamide. The reaction mixture is heated to 70°C and heat under reflux in the course is 6 hours, then cooled, the product wikidot diethyl ether. The precipitate was separated, washed with ether and dried. Output to 7.67 g (86.4%), oil.

The infrared spectrum, cm-1: 1720 (O-C=O)

C35H48O2PBr

Calculated, %: C 68,74; N 7,86; P 5,07

Found, %: C 69.01; H Of 8.06; P of 5.05

An NMR spectrum31P, chloroform, δ ppm 25,55

Example 4. Synthesis of 2-(carboxyester)ethyltriphenylphosphonium bromide:

To a solution 3,34 g (0,01 mol) of triphenylmethylchloride in 50 ml of benzene is added a solution 6,10 g (0,02 mol) of n-hexadecylamine. The reaction mixture is heated to 75°C and heat under reflux for 6 hours, then cooled, the product wikidot diethyl ether. The precipitate was separated, washed with ether and dried. Output 5,97 g (93.43%), oil.

The infrared spectrum, cm-1: 1720 (O-C=O)

C37H52O2PBr

Calculated, %: C 69,48; N 8,13; P 4,85

Found, %: C 69.11; H 8,46; P 5,17

An NMR spectrum31P, chloroform, δ ppm 25,80

Example 5. Synthesis of 2-(carboxylatomethyl)ethyltriphenylphosphonium bromide:

To a solution 3,34 g (0,01 mol) of triphenylmethylchloride in 50 ml of benzene is added a solution of 6.66 g (0,02 mol) of n-octadecylamine. The reaction mixture is heated up to 80°C and heat under reflux for 7 hours, then cooled, the product wikidot diethyl ether. The precipitate was separated, washed with EPE is om, dried. Output 5,97 g (93.43%), oil.

The infrared spectrum, cm-1: 1720 (O-C=O)

C39H56O2PBr

Calculated, %: C 70,16; N 8,40; P 4,65

Found, %: C 70.71; H 8,64; P 4,95

An NMR spectrum31P, chloroform, δ ppm 25,88

Example 6. Study of biological activity

Fungicidal and bactericidal activity of salts of Quaternary phosphonium formula I were investigated on the test cultures: Candida albicans, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis [Pershin GN. Methods of experimental chemotherapy. - M.: Medicine, 1971. - 245 C.]. For evaluation of biocidal activity of the investigated substance of the formula I were made in the wells apparitional nutrient medium. Of bactericidal and fungicidal activity was judged by the presence of zone of inhibition of growth of the test cultures, which is formed around the hole with the test substance. The results of the study fungicidal and bactericidal activity of 2-(carboxy-n-alkyl)ethyltriphenylphosphonium bromides of formula I are presented in the table.

Fungicidal and bactericidal activity of 2-(carboxy-n-alkyl)ethyltriphenylphosphonium bromide
No.ConnectionThe zone of inhibition of growth of bacteria and fungi, R (mm)
Stphylococcus aureus Escherichia coliPseudomonas aeruginozaProteus mirabilisCandida albicans
1.124.581015
2.146101218
3.1488416
4.1688818
5.1266416

advantages of the proposed connection is they have high bactericidal and high fungicidal activity at low concentrations. In addition, they are thermally stable (according to the method of thermogravimetry and scanning calorimetry) to of 224.8°C and not collapse under the action of the soap solution, because they are cationic surfactants, which makes them promising drugs and disinfectants.

The claimed technical solution meets the criterion of "novelty", presented to the invention, because of the investigated level of technology not identified technical solutions characterized by these traits, leading to the implementation of the claimed technical result of the claimed technical solution, which is the synthesis of new stable, not subject to hydrolysis, fofanah compounds, alkyl betaines (I)having as bactericidal, fungicidal activity, resistant to surfactants that extends the range of known means specified destination.

The claimed technical solution meets the criterion of "inventive step", presented to the invention, since it is not obvious to a person skilled in the art due to the fact that the claimed technical solution provides an implementation of objectively existing in practice, contradictions, is not solvable is by means of conventional design, namely investigated prior art it is known that ammonium salt unlike fofanah decompose at temperatures over 130°C, and the resulting salts of the claimed technical solution is stable even at a temperature of not less than of 224.8°C. (according to the method of thermogravimetry and scanning calorimetry) and not collapse under the action of the soap solution, because they are cationic surfactants, which makes them promising drugs and disinfectants, thus we can conclude that the results are not obvious to a person skilled in this technical field.

The claimed technical solution meets the criterion of "industrial applicability", as may be implemented on any appropriate facility using standard equipment known materials and technologies.

2-(Carboxy-n-alkyl)ethyltriphenylphosphonium bromides of General formula I,

where R=n-C10H21n-C12H25n-C14H29the h16H33n-C18H37,
having bactericidal and fungicidal activity at low concentrations, heat resistance and resistance to surfactants.



 

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5 cl, 12 ex

FIELD: chemistry.

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72 cl, 1 tbl

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72 cl, 1 tbl

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26 cl, 14 dwg, 16 ex

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10 cl

FIELD: chemistry.

SUBSTANCE: invention refers to organic chemistry, namely, to method of production of functionally substituted fullerenes to be applied as complexing agents, sorbents, biologically active compounds, as well as for production of new materials with specified electronic, magnetic and optical properties. Substance of the method consists in production of 2,3-fullero[60]-7-phenyl-7-phosphabicycklo[2.2.1]heptanes of formula (I) as resulted from reaction of fullerene C60 and phenylphospholane with catalyst Cp2TiCl2 added in toluol medium at temperature 140-160°C within 4-8 hours.

EFFECT: new method of selective production of functionally substituted fullerenes with end product yield 46-68%.

9 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: present invention concerns the salts containing bis(trifluoromethyl)imide anions and saturated, partially or completely unsaturated heterocyclic cations, method of production and application thereof as ionic liquids.

EFFECT: production of new salts to be used as ionic liquids.

19 cl, 5 ex

FIELD: chemistry.

SUBSTANCE: claimed invention relates to copolymers of diallylaminophosphonium salts with sulphur dioxide demonstrating antimicrobial activity with respect to a number of bacteria, as well as to yeast-like fungi and spores, and can be applied as antiseptic and disinfecting means. Claimed copolymers of diallylaminophosphonium salts with sulphur dioxide aree characterised by general formula where A=Cl- or BF4-. They are soluble in methanol, DMSO, DMFA or if A=Cl- are soluble in water. They are obtained by copolymerisation of equimolar amounts of sulphur dioxide and diallylaminophosphonium salt, selected from tris(diethylamino)diallylaminophosphonium chloride or tris(diethylamino)diallylaminophosphonium tetrafluoroborate.

EFFECT: obtaining novel efficient and low-toxic compounds which do not cause corrosion of processed metals.

2 cl, 3 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to ionic liquids based on a cation of formula (1): where substituting groups R1-R9 are selected from hydrogen, alkyl; any carbon atom in R1-R9 can be substituted with a -O-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2- or -SO3- group; X is S, O or C; R8 and R9 exist only when X is carbon; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(FSO2)3C]-, [RCH2OSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [B(OR)4]-, [N(CF3)2]-, [N(CN)2]-, [AlCl4]-, PF6-, BF4-, SO42-, HSO4-, NO3-; where R is hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, Rf is a fluorine-containing substituting group.

EFFECT: obtaining new ionic liquids with improved electrochemical properties.

15 cl, 18 ex, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to ionic liquid used in electrical energy accumulation devices and as a solvent which contains a cation of general formula where X1, X2 and X3 denote N, O, S or C; R1-R11, X1, R1, R2 and R3, X2, R6, R7 and R8, X3, R9, R10 and R11 can form ring structures; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(RfSO2)3C]-, [(FSO2)3C]-, [ROSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [R2P(O)O]-, [RP(O)O2]2-, [(RO)2P(O)O]-, [(RO)P(O)O2]2-, [(RO)(R)P(O)O]-, [Rf2P(O)O]-, [RfP(O)O2]2-, [B(OR)4]-, [N(CN)2]-, [AlCl4]-, PF6-, [RfPF5]-, BF4-, [RfBF3]-, SO42-, HSO4-, NO3- I-, bis(oxalate)borate; R, R1-R11 are selected from hydrogehn, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl and heterocyclyl, halogen, CN- or NO2-; the carbon in R and R1-R11 can be substituted with O-, -Si(R')2-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2-, -SO3-, -N= -N=N-, -NH-, -NR'-, -N(R')2-, -PR'-, -P(O)R4 -P(O)R'-O-, -O-P(O)R'-O- and -P(R')2=N-; where R' denotes alkyl, fluoroalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, phenyl or heterocyclyl; Rf denotes a fluorine-containing substitute.

EFFECT: obtaining novel ionic liquids which are stable in liquid state in a wide temperature range.

14 cl, 76 ex, 3 dwg

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