CZ36084U1 - Polyvalent decontaminating agent to eliminate the effects of chemical and / or biological warfare agents - Google Patents

Description

The technical solution relates to the field of decontamination of materials, specifically a polyvalent decontamination agent for eliminating the effects of chemical and/or biological warfare agents.

State of the art

Infections caused by microorganisms or poisoning caused by chemical substances represent a global problem. An example of the intentional misuse of chemical or biological substances is their use in war as combat agents or for terrorist purposes. A combat chemical substance in the form of a weapon hits the object of attack with inorganic or organic compounds that have an irritating or toxic effect on the organism. The mechanism of action is different - from targeted damage to certain parts of the body, such as blocking the cholinesterase enzyme in the synapses of neurons in nerve agents, to systemic action, when the substance is toxic to the entire body, such as mustard gas. Chemical weapons are very effective when used against unprotected manpower or when misused against the civilian population. A biological weapon is based on the action of a living organism, a pathogen, i.e. bacteria, fungi, viruses or a substance produced, most often a toxin. Their target is most often a person, in whom they are intended to induce a disease, such as e.g. infectious diseases or poisoning resulting in significant impairment of health or even death. The use of biological warfare agents can be assumed, for example, by dispersing powder, creating an aerosol cloud, infecting animals or contaminating food chains, and they can then spread from person to person.

In the case of chemical accidents or microbial infections, when there is unintentional contamination of living and non-living surfaces, as well as in the case of intentional misuse, e.g. by terrorism, it is necessary to react quickly and thus limit further contact and spread of chemical or biological agents. For these cases, so-called decontamination agents, or their mixtures, are used and newly developed. Decontamination mixtures are often focused on only one area of application, e.g. decontamination of chemical substances, as they often contain only one active ingredient and several additives facilitating application. In the case of multi-component decontamination mixtures, the substances often degrade with each other, and therefore it is necessary to mix them just before use (Capoun, T.; Krykorková, J. Ensuring of individual decontamination of dangerous chemicals in the fire rescue service of the Czech Republic. Part 2: Comparison of decontamination effectiveness of selected means and procedures. The science for population protection. 2014, 6 (2), 1-12). The main intention is therefore to find a decontamination mixture with one active ingredient that has a polyvalent effect, i.e. it is applicable against both chemical and biological agents.

Quaternary ammonium salts are among the substances used worldwide in a wide variety of industries, such as the food, pharmaceutical, and textile industries. They are used as disinfectants, surfactants, softeners, and antistatic agents. Benzalkonium salts, or N-alkyl-N-benzyl-N-dimethylamines, or BACs with an alkyl chain length of C10 to C18, are commonly used in the food industry, among other things, because they protect against contamination of food, drugs, and other products by various microorganisms, including molds. They extend shelf life and increase safety (Grillitsch, B.; Gans, O.; Kreuzinger, N.; Scharf, S.; Uhl, M.; Fuerhacker, M. Environmental Risk Assessment for Quaternary Ammonium Compounds: A Case Study from Austria. Water Sci. Technol. 2006, 54 (11-12), 111-118. https://doi.org/10.2166/wst.2006.840). Benzalkonium salts with a C12 chain are usually very effective against fungi, with a C14 chain against Gram-positive bacteria, and with a Ci6 chain against Gram-negative bacteria (Daoud, N.; Dickinson, N.; Gilbert, P. Anti-Microbial Activity and Physicochemical Properties of Some Alkyldimethylbenzylammonium Chlorides. Microbios 1983, 37 (148), 73-85). In the Czech Republic, it is commonly

- 1 CZ 36084 UI used preparation benzalkonium bromide, or a mixture of benzalkonium salts with different chain lengths, a preparation known as Ajatin for skin disinfection.

Another group of compounds that is structurally similar to benzalkonium salts are compounds containing two hydroxyethyl groups linked to a quaternary nitrogen. Compared to benzalkonium salts, these substances are not as widely used. A commercially available representative of this group is benzoxonium chloride or benzyl-dodecyl-bis(2-hydroxyethyl)azanium chloride, which is most often used against biological agents as a mucosal disinfectant in the form of gargles, lozenges or oral sprays. In dentistry it is used to remove dental plaque, it is also used in hospitals to disinfect surfaces and medical instruments, it is also very often used in ophthalmology, where it is used as a preservative, as stated, for example, in patent documents CA2025728C or US20060211753A1 or Labranche, L.-P.; Dumont, S. N.; Levesque, S.; Carrier, A. Rapid Determination of Total Benzalkonium Chloride Content in Ophthalmic Formulations. J. Pharm. Biomed. Anal. 2007, 43(3), 989-993. https://doi.org/10.1016/jjpba.2006.09.022.

Some quaternary ammonium salts have also been tested to accelerate the decomposition of toxic chemicals such as organophosphates, which are used as pesticides in agriculture. A typical representative of pesticides is, for example, Fenitrothion. However, there are substances structurally similar to pesticides that have much higher toxicity. They have been abused several times as chemical warfare agents due to their neurotoxic effects. These are nerve agents such as tabun, soman or sarin (Tiwari, S.; Ghosh, K. Κ.; Marek, J.; Kuca, K. Cationic Micellar-Catalyzed Hydrolysis of Pesticide Fenitrothion Using α-Nucleophiles. Lett. Drug Des. Discov. 2010, 7 (3), 194-199. https://doi.org/10.2174/157018010790596650). Organophosphorus pesticides are often used experimentally as so-called model substances for the above-mentioned nerve agents. However, the tested substances from the group of quaternary ammonium salts did not demonstrate sufficient decontamination efficiency.

The essence of the technical solution

The subject of the technical solution solving the above problem is a polyvalent decontamination agent that is effective simultaneously against chemical and/or biological contaminants of the type of warfare agents, i.e. it has a disinfecting effect on a wide range of bacterial strains in free and sessile form, on a wide range of viruses, but at the same time it also ensures the removal of organophosphorus pesticides and chemical nerve agents, i.e. it exhibits a polyvalent decontamination effect, the use of which is particularly suitable in the event of accidents, pandemics or terrorist attacks.

The subject of the technical solution is therefore a polyvalent decontamination agent for eliminating the effects of chemical and/or biological warfare agents. The agent is a quaternary ammonium salt of the general formula I

OH (I)

-2CZ 36084 UI where:

R is an alkyl chain with a carbon number of C10, C12, C14, C16 or C18,

X is an anion in the form of a halide: bromide, chloride or iodide.

In a preferred embodiment, the quaternary ammonium salt is selected from the group: benzyl-decyl-bis(2-hydroxyethyl)azanium chloride, benzyl-dodecyl-bis(2-hydroxyethyl)azanium chloride, benzyl-tetradecyl-bis(2-hydroxyethyl)azanium chloride, benzyl-hexadecyl-bis(2-hydroxyethyl)azanium chloride and benzyl-octadecyl-bis(2-hydroxyethyl)azanium chloride.

The quaternary ammonium salt according to the technical solution can be used for decontamination of solid and/or liquid and/or gaseous forms of contaminants such as chemical and/or biological warfare agents, and is suitable for living or non-living surfaces, i.e. for various materials such as tools, equipment, terrain, etc., or for people, directly on the skin. The quaternary ammonium salt is used in a liquid application form.

The quaternary ammonium salt is preferably used in the form of a decontamination preparation, which is in the form of a hydrolysis solution or a disinfectant solution or an aerosol. The quaternary ammonium salt can thus be applied to affected material and/or persons by spraying the solution or aerosol onto the respective contaminated surface.

The decontamination uses the polyvalent effects of the decontamination agent of general formula I. The term polyvalent effect includes the ability of this decontamination agent to have a disinfectant effect on a wide range of nosocomial bacterial strains both in free, i.e. planktonic form, and in a more resistant sessile, i.e. biofilm form. In addition, they include the effect on the model strain Francisella tularensis, which is included in the list of microorganisms that can be misused for bioterrorism. Furthermore, the ability of the decontamination agent to eradicate representatives of enveloped viruses, preferably murine cytomegalovirus (MCMV), is used. Last but not least, the decontamination agent has the ability to detoxify chemicals of the type of organophosphate pesticides, such as Fenitrothion, which are also model substances of more toxic nerve agents, such as sarin, soman or tabun. The decontamination agent therefore appears to be a universal active ingredient in decontamination mixtures for use with chemical and biological agents for use by the armed forces, the integrated rescue system, or other special cleanup components in the event of accidents, pandemics, or terrorist attacks.

For this purpose, the antimicrobial activity against pathogenic resistant strains of bacteria, more resistant biofilm forms of bacteria, the determination of antimicrobial activity against the bacterium F. tularensis as a potentially exploitable model organism and the determination of virucidal efficacy on a representative of enveloped viruses were evaluated. Furthermore, the ability of these decontamination agents to detoxify substances such as organophosphates potentially exploitable as chemical weapons was measured.

The advantages of the polyvalent decontamination agent according to this technical solution lie mainly in the fact that it is effective simultaneously against chemical and/or biological contaminants of the type of warfare agents, i.e. it has a disinfecting effect on a wide range of bacterial strains in free and sessile form, on a wide range of viruses, but at the same time it also ensures the removal of organophosphorus pesticides and chemical nerve agents.

CZ 36084 UI

Example of implementing a technical solution

The antimicrobial effect of the decontamination agent of general formula I against Gram-positive and Gram-negative strains of bacteria is confirmed by examples. Decontamination agents with a hydrocarbon chain length of C12-14 are effective mainly against Gram-positive bacteria, while decontamination agents with a hydrocarbon chain length of C14-16 have a high effectiveness against Gram-negative bacteria. The antimicrobial effect is confirmed, namely, for the bacterial strains Staphylococcus aureus (Cl 947), methicillin-resistant Staphylococcus aureus (Cl 926), Staphylococcus epidermidis (C1936), Vancomycin-resistant Enterococcus (S2484), Escherichia coli (A1235), non-producing extended-spectrum beta-lactamases (ESBLs) Klebsiella pneumoniae (C1950), producing extended-spectrum ESBLs Klebsiella pneumoniae (C1914) and multiresistant Pseudomonas aeruginosa (A1245). The decontamination agents were comparable, or in some cases even better, than commercially used benzalkonium chloride salts, where a broad spectrum of activity ensures coverage of the biological part of the decontamination agent, as shown in Example 2. In determining the effectiveness in a 5-minute exposure time on the methicillin-resistant Staphylococcus aureus strain (Cl926), the substances demonstrated slightly worse efficacy than the Ajatin preparation containing benzalkonium chloride, but the efficacy can nevertheless be considered sufficient. It is possible to accept that at the expense of reduced disinfection efficacy, significant disinfection efficacy was demonstrated for organophosphorus compounds, as shown in Example 1, which benzalkonium-type substances do not have.

For one strain (Staphylococcus aureus - Cl947), the effectiveness of the substances on the so-called biofilm form of the bacterium was also confirmed, with the assumption of effectiveness also on other strains, which are generally considered to be more resistant and more common. In the examples, the minimum biofilm eradicating concentration or MBEC of the decontamination agent of general formula I with a hydrocarbon chain length of C12, C14 and Ci6 was determined. These decontamination agents were confirmed as suitable for the eradication of the respective bacterial biofilm, as shown in Example 4. The justification for the higher resistance of the biofilm is the fact that it is a community of microorganisms attached to a certain type of surface. The cells inside the biofilm are able to communicate with each other and specialize in various functions. The surface of the bacterial cells is protected by an extracellular matrix providing protection against external influences. This makes the microorganisms that are part of the biofilm resistant and for their eradication it is necessary to use antimicrobial substances in a higher concentration compared to the floating form of bacteria.

In addition, decontamination agents of the general formula I with a hydrocarbon chain length of C12, C14 and C16 are advantageous for the eradication of highly virulent bacteria, preferably Francisella tularensis. This Gram-negative bacterium causes a serious infectious disease called tularemia, manifested by an ulcer at the site of entry and involvement of the lymph nodes. F. tularensis (type A) is also included in the list of substances potentially exploitable as biological weapons, where infection occurs even with an extremely low dose of spores, for example in the form of an aerosol.

Another significant effect of the polyvalent decontamination agent is the confirmation of the virucidal efficacy of the decontamination agent of general formula I (preferably C12 and C14) on representatives of enveloped viruses, preferably on MCMV, where the efficacy met the limit of a 4-log decrease in virus titer for fully virucidal substances according to ČSN ΕΝ 14476+A2 (2020), as shown in Example 6.

Polyvalent decontamination agents of general formula I also have the ability to hydrolyze the P-0 ester bond of toxic organophosphates, and their efficiency increases with increasing hydrocarbon chain length C10 < C12 < C14 < Ci6 < Cis. These substances achieve the highest hydrolytic efficiency when the so-called critical micelle concentration or CMC is exceeded, when micelles are formed in the quaternary ammonium salt solution, which attract the organophosphate to each other due to surface charge, solubilization, electrostatic interactions and polarization and accelerate its decomposition. Hydrolysis of the ester bond of organophosphates thus produces a less toxic product. Adjusting the pH of the decontamination agent solution to values of 10 to 11 also plays a significant role, which additionally enhances the hydrolytic effect, as shown in Example 1. It is clear from the results that when the CMC is exceeded, the decomposition reaction, i.e. detoxification, is significantly accelerated. Increasing the concentration of some decontamination agents

-4CZ 36084 Ul of general formula I further above the CMC, however, does not always lead to further acceleration of the reaction; on the contrary, after the substrate is exhausted, the so-called empty micelle syndrome occurs and the reaction slows down, which are observed with the substances BOX Cl ^- Cio and BOX Cl ^- C12. On the other hand, decontamination agents with longer chains (C14-18), which are in significantly lower concentrations, but still have a more significant effect on the decomposition, did not show this phenomenon in the observed concentrations.

Example 1: Determination of hydrolytic efficiency

Table 1 shows the results of the hydrolytic efficiency measurements of the decontamination agents of general formula I acting on the model organophosphate Fenitrothion. The table includes the concentration series of each decontamination agent with concentrations above and below the CMC, the CMC values below each substance, the half-life and the rate constant. The designation BOX CF Cio-is is used for decontamination agents of general formula I that differ in the length of the long side chain, these are homologues.

10 ⁴ k (s ¹ ) is the rate constant of the pseudo-first-order decomposition reaction and expresses the rate at which the substrate decomposes in an excess of solvent, it is an aqueous solution of the decontamination agent of the general formula I. TV2 (min) indicates the half-life - the time it takes for 50% of the substrate (Fenitrothion) to decompose. The influence of pH on the monitored parameters is obvious from the table. The table does not include standard decontamination agents of a similar type for comparison, as this is a new application.

Table 1 - Determination of hydrolytic efficiency pHH,t37°C pHHM37°C

Decontamination agent CMC (mmol) c (mM) 10* k (s-1) TU (min) 10* k (s-1) TI .2 (min) 500 6.2 18.6 2.3 50.3 BOX CT CIO 100 12.82 9 3.97 29.2 50 12.68 9.1 3.77' 30.7 (48.36) 10 0.5 230.8 0.18 606.3 5 0.35 323.2 - - WO 8.17 14.1 1.67 69.1 BOX Cl- Cl 2 50 9.35 12.4 2.35 49.3 10 UmI 14 2.65 43.5 (8.71) 5 5.93 19.5 1.15 100.8 I i,8 64.5 - - 10 24.62 4.7 6.77 17.1 BOXCFC14 5 23.62 4.9 5.82 19.9 I li,28 10.2 2.02 57.5 (3.00) 0.5 3.8 30.5 1.12 103 0.1 1.17 98.8 0.5 230.8 10 50.73 2.3 11.56 10.0 BOX Cl C16 5 49.06 2.4 11.14 10.4 1 12.32 9.4 3.97 29.2 (1.16) 0.5 6.47 17.9 2.3 50.3

-5CZ 36084 Ul

0.1 1.77 653 1.1 105.2 5 23.3 5 6.98 16.5 BOX Ci C18 1 13.95 8.3 437 26.4 0.-5 7 82 14.8 -J 38 9 (0.45) 04 E87 62 0.82 142.5 0.05 0.83 13K4 0.28 404.1

Example 2: Evaluation of antibacterial efficacy

Table 2 shows the determination of the antimicrobial efficacy of the decontamination agents of general formula I using the broth microdilution method (CLSI, 2018) for four Gram-positive and four Gram-negative bacterial strains. The result is the determination of the minimum inhibitory concentration or MIC after 24 and 48 hours, and the determination of the minimum bactericidal concentration or MBC after 48 hours. BAC denotes benzalkonium-type reference substances with different chain lengths (Cn-ie). BOX are the tested decontamination agents of general formula I with different side chain lengths (Cio-is).

Table 2 - Determination of antibacterial efficacy against a broad spectrum of bacteria

MIC {psnol/Lfr incubation

MBC 4Sh incubation

BAC B-r C12 BACBrC14 BAC St' C16 box and oio 8OX a· C12 BOX and C14 BOX G <16 sox a- cis 1.95 0.98 0.58. 3.91-7.61 1.95 0.49 0.93 0.49- 3.91 StapAyfoaNXUS oureus + 1^95 0.95-1.95 0.98 3.91-7.81 1.35- 0.98 6.98 -1.95 0.98-3.91 1.95 0.93 - 1.95 1.58 3.91 — 7.81 1.95 0.98-2.95 2.95 0.93- 3.92 MeiftÝdim /east 15.53 3.91 3.91 7.81 -15.63 15.63 1.95-7.81 1:9.5—7:31 15.63 golden + 15.63 3.31 7.31 7.31 -15.63 15.63 3.91-7.81 3.91 — 7.31 15.63 15.53 3.91 7.81 15.63- 31.25 15.63 7.81-15.63 7.81 - 25.63 15.63 Step&ytocQCťtfs 15.53 0.93 - 1.95 1.95-3.91 31.25-62.5 7.81-15.63 1.95-3.91 1.95-3.91 3.91-15.63 e^ermídřs + 15.63 1.55 1.95-3.91 31.25-62.5 15.63 3.91-7.81 3.91-7.31 7.S1 -13.63 15.53 1.95 1.95 - 7.81 62.5 15.63 3.91 — 7.81 3.91 — 7.81 >51.25 cut. 31.25 3.91 15.63 125 15.63 7.83. 7.82 15.63 &?fero£<xttJ5· + 31.25 3.51 15.63 325 15.63-31.25 15.63 7.81 15.63 31.25 7.81 15.63 125 25.63-31.25 15.63 7.81 25.63 — 31.25 15.53 7.31 31.25 250 481 25.63-31.25 > 62.5 15.63 — 31.25 What is Escfceráiřua? - 15.63 7.31 525 2SG 7.81 15.63 — 31.25 > 62.5 25.63-31.25 15.55 7.31 62.5 250 7.81 15.63 — 31.25 > 62.5 15.53-31.25 ftebsíeflíj piteti/nankne - 7,S1 15.63 52.5 250-500 31.25 31.25 > 62.5 >51.25 fS&L- 7.81 15.63 62.5 259-500 31.25 31.22 >52.5 >51.25 7.81 15.63 62.5 25O-SOO 31.25 31.25 > 52.5 >31.25 Ktebsfeffa - 15.53 7.31 62.5 590 31,^= 31.25 >62.5 >31.25 15.53 7.31 62.5 500 31.25 32.25 >52.5 >51.25 15.63 7,S1 62.5 - 125 590 32.25 31.23 > 62.5 >51.25 PseiwfcwiDíWTS íFerwgíritosa ¹ - 250 7,3.1-51,.25 7.82 -125 >500 125 > 62.5 > 62.5 >81.25 Mij/ř/rezfstďnt. 250 - 500 15.63-31.25 225 >500 125 > 62.5 > 62.5 >51.25 250-500 15.63- 31.25 12.5 - 2SO > 500 3.25 > 62.5 >52.5 >31.25

Example 3: Evaluation of antimicrobial efficacy against F. tularensis

The graph in Fig. 1 and Table 3 show the evaluation of the antimicrobial efficacy of the decontamination agents of general formula I against F. tularensis (LVS) using fluorescence flow cytometry (LIVE/DEAD™ BacLight™ Bacterial Viability and Counting Kit). The duration of the decontamination agent exposure was 5 minutes. The results were compared with standards (Ethanol 70%,

-6CZ 36084 UI

Ajatin 0.1%). PK is a positive control, where phosphate buffered saline (PBS) was used instead of the decontamination agent. The results show that the most effective substance is the C12 homologue, which at concentrations of 0.1% and 0.05% shows a relatively high efficiency comparable to the commercially used Ajatin. With increasing chain and decreasing concentration, the activity decreases significantly.

Table 3 - Determination of bactericidal efficacy against Francisella tularensis

Substance Live bacteria [%] Positive control 96.07 ± 1.11 ET 70% 13.45 ±4.88 AJ 0.1% 4.88 ±5.16 BOXC12 0.1% 5.73 ± 8.77 BOX C12 0.05% 14.06 ± 12.30 BOX C12 0.01% 71.38 ±30.17 BOXC14 0.1% 19.53 ± 17.24 BOX C14 0.05% 41.84 ±20.45 BOX C14 0.01% 70.96 ±7.91 BOXC16 0.1% 53.89 ±29.80

Example 4: Determination of the minimum biofilm eradicating concentration (MBEC)

The S. aureus biofilm was formed on a polystyrene surface using the MBEC assay from Innovotech (Ceri, H.; Olson, Μ. E.; Stremick, C.; Read, R. R.; Morek, D.; Buret, A. The Calgary Biofilm Device: new technology for rapid determination of antibiotic susceptibilities of bacterial biofilms. J. Clin Microbiol. 1999, 37 (6), 1771-6; https://doi.Org/10.1128/JCM.37.6.1771· 1776.1999) for 24 hours. It was then exposed to decontamination agents of general formula I with hydrocarbon chain lengths of C12, C14 and C16 for 24 hours. Table 4 summarizes the MBEC (minimum biofilm-eradicating concentration) values. The graph in Fig. 2 shows the MBEC values of these substances compared to the standards (benzalkonium bromide C12, C14, Cie) and the MIC values mentioned above. The graphs show the increased resistance of the biofilm form of the bacteria and the comparable or better efficacy of benzoxonium-type decontamination agents compared to the more commonly used benzalkoniums.

Table 4 - Determination of efficacy against biofilm (S. aureus)

Substance MBEC [μΜ] BAC Br C12 62.5 - 250 BAC Br C14 31.25 -62.50 BAC Br C16 15.63-31.25 BOX Cl C12 31.25 -62.50 BOX Cl C14 31.25 BOX Cl C16 15.63

Example 5: Determination of bactericidal activity

A quantitative test was performed using a suspension to determine bactericidal activity according to ČSN ΕΝ 13727+A2 (2016). The exposure time was 5 minutes, the initial concentration of the suspension of the bacterial strain methicillin-resistant Staphylococcus aureus (Cl926) was 1.18E+09 CFU/ml. The standard for comparing the effectiveness is Ajatin. The results are shown in Table 5. The neutralizing agent is a mixture of substances that prevent further antimicrobial action of the tested decontamination agent. It is therefore clear that for the decontamination agents BOX CF C12 and BOX CF C14,

-7 CZ 36084 UI that the decrease in bacterial growth by 4 orders of magnitude (99.99%) occurs in the first five minutes and does not change further even with the addition of a neutralizing agent. Due to the limit of the method, the eradication of bacteria is expressed as <100. The decontamination agents are comparably effective with Ajatin as a standard. In the case of the substance BOX Cl ^- Ci6, lower activity is evident due to the increase in colonies after neutralization. This decontamination agent is therefore not sufficiently effective.

Table 5 - Determination of bactericidal activity over time

CFU/mL Water Nemraliza _{βoch cj} cni cmídio (NČ) BOX ClC12 + NC BOX Cl- C14 BOX Cl- C14 -řNČ BOX ClC16 BOX Cl· Cl6 -r NČ Ajatin 9.6E<05 6.13E+05 < 100 < 100 < 100 < 100 1.16E<02 E28E+03 < 100

Example 6: Determination of virucidal efficacy on enveloped virus

The determination of the virucidal activity of decontamination agents against murine cytomegalovirus (MCMV) was performed using a quantitative suspension test. The virus titer was evaluated using the Spearman-Karber method and expressed as log 10 TClD50/ml. In accordance with EN 14476 for virucidal activity by disinfection, the substance should demonstrate a reduction in the virus titer by at least 4 orders of magnitude, which corresponds to 99.99% inactivation. To distinguish between virus-induced cytopathic changes and the toxic effect caused by the tested decontamination agents, morphological changes in a single layer of cells were monitored. The measurement results are shown in Table 6 below. The highest efficiency was shown by the substance BOX Ci2, where the decrease in the virus titer was more than 5 orders of magnitude at a concentration of 0.01% (w/v%). For substances at a concentration of 0.1% (w/v %), the decrease could not be determined completely accurately (marked >), because at this concentration the decontamination agent already affected the cell culture on which the virus was cultivated (Table 6).

Table 6 - Determination of virucidal efficacy against MCMV

Disinfection 0' 5' AlogT CID50 concentration BOX C12 7.83 4.49 >3.34 0.01% BOX C12 9 3.67 5.33 0.01% BOX C14 7.49 5.49 >2.34 0.1% BOX C14 9 5.66 3.34 0.01% BOX C16 7.83 4.49 >3.34 0.1% BOX C16 6.83 7.33 -0.5 0.01%

Industrial applicability

The polyvalent decontamination agent for eliminating the effects of chemical and/or biological warfare agents according to this technical solution can be used in particular by the armed forces, the integrated rescue system or other units for decontamination in the event of accidents, pandemics or terrorist attacks.

Claims (2)

1. Quaternary ammonium salt of general formula I 5 (I) where: R is an alkyl chain with a carbon number of C10, C12, C14, C16 or C18, X is an anion selected from bromide, iodide chloride. 2. The quaternary ammonium salt according to claim 1, selected from the group 10 benzyl-decyl-bis(2-hydroxyethyl)azanium chloride, benzyl-dodecyl-bis(2-hydroxyethyl)azanium chloride, benzyl-tetradecyl-bis(2-hydroxyethyl)azanium chloride, benzyl-hexadecyl-bis(2-hydroxyethyl)azanium chloride and benzyl-octadecyl-bis(2-hydroxyethyl)azanium chloride.