Antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (ha-31m), 3,3-diethoxy-1-propene (MAR-31), or mixture thereof, and method for preparing same

Abstract

The present invention relates to an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a preparation method therefor. The antibacterial, antifungal, and antiviral composition according to the present invention has low toxicity to the human body, is environmentally friendly, and exhibits a remarkably superior biocidal (disinfection) effect against various microorganisms [bacteria (including spores), fungi, and viruses]. Furthermore, the mixture has the characteristic of simultaneously exerting biocidal (disinfection) effects against various microorganisms.

Description

A composition for antibacterial, antifungal, and antiviral use comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a method for preparing the same

[0001] The present invention relates to an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or a mixture thereof, and a method for preparing the same.

[0002] Humans are exposed to numerous microorganisms in their daily lives, and some bacteria, fungi, and viruses cause various infections in the human body. Due to the risks associated with bacterial, fungal, and viral diseases, a variety of chemical products with antibacterial, antifungal, and antiviral activities are being released.

[0003] Due to the increased use of surgical equipment resulting from recent advancements in medical technology and the COVID-19 pandemic, the demand for sterilization and disinfection products is increasing, and the market for biocides and disinfectants is continuously growing.

[0004] Disinfectants used as biocides must satisfy strict conditions, such as broad-spectrum sterilization efficacy, rapid efficacy, maintenance of product stability, and low toxicity to the human body. Although many biocides and disinfectants have been developed and marketed to date, issues regarding safety and toxicity are constantly being raised. In particular, glutaraldehyde (GA), which is currently the most widely used substance in Korea, has already been banned from use in the healthcare sector in Europe and is expected to be banned in Korea soon as well, creating an urgent need for the development of alternative substances.

[0005] Through in-depth research, the inventors have devised 2-oxoacetic acid (CAA-21), 3-hydroxypropionaldehyde hybrid system (HA-31M), 3,3-diethoxy-1-propene (MAR-31), or mixtures thereof that have low toxicity to the human body, are environmentally friendly, and have a simultaneous killing effect against various microorganisms (bacteria, bacterial spores, fungi, and viruses). Instead of using separate disinfectants for each microorganism, they have discovered a biocide capable of simultaneously eradicating various microorganisms (bacteria, bacterial spores, fungi, and viruses) with a single product, and it is expected that this will lead to the development of a groundbreaking product in this field.

[0006] The objective of the present invention is to provide an antibacterial, antifungal, and antiviral composition that has low toxicity to the human body, is environmentally friendly, and has a biocidal effect against various microorganisms (bacteria, bacterial spores, fungi, and viruses), and a method for manufacturing the same.

[0007] The present invention provides an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid of Formula 1 (CAA-21), 3-hydroxypropionaldehyde hybrid system of Formula 2 (HA-31M), 3,3-diethoxy-1-propene of Formula 3 (MAR-31), or a mixture thereof.

[0008] [Chemical Formula 1]

[0009]

[0010] [Chemical Formula 2]

[0011]

[0012] [Chemical Formula 3]

[0013]

[0014] The antibacterial, antifungal, and antiviral composition of the present invention can be utilized as an eco-friendly, general-purpose biocide and disinfectant.

[0015] The antibacterial, antifungal, and antiviral composition of the present invention has antibacterial activity against one or more bacteria (including bacterial spores) selected from the group consisting of Salmonella Typhimurium, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis. In addition, the antibacterial, antifungal, and antiviral composition of the present invention has sterilizing activity against Bacillus subtilis spores.

[0016] In addition, the antibacterial, antifungal, and antiviral composition of the present invention has antifungal activity against one or more fungi selected from the group consisting of Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0017] In addition, the antibacterial, antifungal, and antiviral composition of the present invention has antiviral activity against the avian influenza virus MS96 / 1996 (H9N2).

[0018] The antibacterial, antifungal, and antiviral composition containing 2-oxoacetic acid (CAA-21) of the above chemical formula 1 is preferably a 0.01% to 5% aqueous solution.

[0019] The composition for antibacterial, antifungal, and antiviral purposes comprising the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Chemical Formula 2 above is preferably a 0.5% to 5% aqueous solution. "3-hydroxypropionaldehyde hybrid system (HA-31M)" refers to a hybrid system substance existing in a dynamic equilibrium state formed by 3-hydroxypropionaldehyde and its hydrate, dimer, etc., as shown in Reaction Scheme 1 below.

[0020] [Reaction Equation 1]

[0021]

[0022] The antibacterial, antifungal, and antiviral composition containing 3,3-diethoxy-1-propene (MAR-31) of the above chemical formula 3 is preferably a 0.01% to 2% aqueous solution.

[0023] In the antibacterial, antifungal, and antiviral composition of the present invention, it is preferable that the mixture of 2-oxoacetic acid of Formula 1 (CAA-21) and 3-hydroxypropionaldehyde hybrid system of Formula 2 (HA-31M), the mixture of 2-oxoacetic acid of Formula 1 (CAA-21) and 3,3-diethoxy-1-propene of Formula 3 (MAR-31), and the mixture of 3-hydroxypropionaldehyde hybrid system of Formula 2 (HA-31M) and 3,3-diethoxy-1-propene of Formula 3 (MAR-31) are each mixed in a ratio of 3:1 to 1:3.

[0024] In addition, the present invention provides a method for preparing an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21) of the following chemical formula 1, comprising the steps of: (a) placing glyoxal of the following chemical formula 4 into a reaction vessel together with concentrated hydrochloric acid (c-HCl) and sodium nitrite (NaNO2) and heating; (b) adding concentrated nitric acid (HNO3) to the reaction product of step (a) and heating; (c) adding hydrogen peroxide (H2O2) to the reaction product of step (b) and heating, adding manganese dioxide (MnO2) and stirring until bubble generation stops after the reaction is finished, and then removing the remaining hydrogen peroxide. and (d) a step of removing solids by filtration after stirring the reaction product of step (c) to obtain a product in the form of a clear aqueous solution, and further obtaining a final aqueous solution product of high concentration (50%) [2-oxoacetic acid (CAA-21) of Formula 1 below] by low-pressure concentration in a concentrator.

[0025] [Chemical Formula 1]

[0026]

[0027] [Chemical Formula 4]

[0028]

[0029] In addition, the present invention provides a method for preparing an antibacterial, antifungal, and antiviral composition comprising a 3-hydroxypropionaldehyde hybrid system (HA-31M) of the following chemical formula 2, comprising the steps of: (a) adding 3,3-diethoxy-1-propanol of the following chemical formula 5 and 2N H2SO4 to a reaction vessel and stirring for 60 minutes at 5°C or lower to terminate the reaction; (b) adding CaCO3 to the solution obtained in step (a) to neutralize it; and (c) stirring the solution obtained in step (b) for 60 minutes at 5°C or lower, and then filtering the reaction solution under reduced pressure to obtain a mixture, which is then diluted with distilled water to a concentration of 10% to obtain a final product in the form of an aqueous solution of the following chemical formula 2 [an antibacterial, antifungal, and antiviral composition comprising a 3-hydroxypropionaldehyde hybrid system (HA-31M) of the following chemical formula 2].

[0030] [Chemical Formula 2]

[0031]

[0032] [Chemical Formula 5]

[0033]

[0034] In addition, the present invention provides a method for preparing an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of the following chemical formula 3, comprising the steps of: (a) placing copper sulfate (CuSO4), water, and dimethyl sulfoxide (DMSO) into a reaction vessel, adding allyl bromide of the following chemical formula 6, heating the reaction mixture, diluting it with distilled water, extracting it with diethyl ether, collecting the organic layer, drying it with calcium chloride (CaCl2), and concentrating it under reduced pressure to obtain allyl alcohol of the following chemical formula 7; (b) a step of adding pyridinium chlorochromate (PCC) and CH2Cl2 to a reaction vessel, adding the allyl alcohol of Formula 7 obtained in step (a) and CH2Cl2 under stirring, and stirring at room temperature until the reaction is complete to obtain propenal of Formula 8; and (c) a step of reacting the propenal of Formula 8 obtained in step (b) in a diethyl ether solvent with ethanol and a catalyst of p-toluene sulfonic acid (PTSA, p-TsOH) to obtain a final product in the form of a clear aqueous solution [an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of Formula 3].

[0035] [Chemical Formula 3]

[0036]

[0037] [Chemical Formula 6]

[0038]

[0039] [Chemical Formula 7]

[0040]

[0041] [Chemical Formula 8]

[0042]

[0043] The antibacterial, antifungal, and antiviral composition according to the present invention has low toxicity to the human body, is environmentally friendly, and has a necrotic effect against various microorganisms (bacteria, bacterial spores, fungi, and viruses).

[0044] Figure 1 shows the antibacterial effect of glutaraldehyde (GA) at different concentrations (0.05% to 2%) against Salmonella Typhimurium.

[0045] Figure 2 shows the antibacterial effects of glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) at different concentrations (0.25% to 2%) against Salmonella Typhimurium.

[0046] Figure 3 shows the antibacterial effects of glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5% to 2.5%) against Salmonella Typhimurium.

[0047] Figure 4 shows the antibacterial effects of 2-oxoacetate (CAA-21) at different concentrations (0.25%–1%) against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.

[0048] Figure 5 shows the antibacterial effects of the 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5% to 2.5%) against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.

[0049] Figure 6 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 2-oxoacetic acid (CAA-21) solution against Salmonella Typhimurium, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.

[0050] Figure 7 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution against Salmonella Typhimurium, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.

[0051] Figure 8 shows the antibacterial effects of a 2% glutaraldehyde (GA) solution and a 2% 2-oxoacetic acid (CAA-21) solution on the spores of Bacillus subtilis.

[0052] Figure 9 shows the antibacterial effect of a 2% glutaraldehyde (GA) solution and a 2% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution on the spores of Bacillus subtilis.

[0053] Figure 10 shows the antibacterial effect of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.25% to 2%) against Salmonella Typhimurium.

[0054] Figure 11 shows the antibacterial effects of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.25–1%) against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.

[0055] Figure 12 shows the antibacterial effect of a 2% solution of 3,3-diethoxy-1-propene (MAR-31) against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa.

[0056] Figure 13 shows the antibacterial effect of a 2% solution of 3,3-diethoxy-1-propene (MAR-31) on the spores of Bacillus subtilis.

[0057] Figure 14 shows the antifungal effects of glutaraldehyde (GA) at different concentrations (0.01% to 2%) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0058] Figure 15 shows the antifungal effects of glutaraldehyde (GA) at different concentrations (0.5% to 2.5%) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0059] Figure 16 shows the antifungal effects of the 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5%–2.5%) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0060] Figure 17 shows the antifungal effects of 1% and 2% solutions of 2-oxoacetic acid (CAA-21) on Aspergillus brasiliensis and Candida albicans.

[0061] Figure 18 shows the antifungal effects of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.01% to 2%) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0062] Figure 19 shows the antiviral effects of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) at different concentrations (0.01% to 2%) against avian influenza virus MS96 / 1996 (H9N2).

[0063] Figure 20 shows the antiviral effects of glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (1%–2%) against avian influenza virus MS96 / 1996 (H9N2).

[0064] Figure 21 shows the antiviral effects of 3,3-diethoxy-1-propene (MAR-31) at different concentrations (0.01% to 2%) against avian influenza virus MS96 / 1996 (H9N2).

[0065] Figure 22 shows the antibacterial effect of a mixture of a 2% solution of 2-oxoacetic acid (CAA-21) and a 4% solution of 3-hydroxypropionaldehyde hybrid system (HA-31M) against Salmonella Typhimurium.

[0066] Figure 23 shows the antibacterial effect of a mixture of 0.25% solution of 2-oxoacetic acid (CAA-21) and 0.25% solution of 3,3-diethoxy-1-propene (MAR-31) against Salmonella Typhimurium.

[0067] Figure 24 shows the antibacterial effect of a mixture of a 2% solution of 2-oxoacetate (CAA-21) and a 4% solution of 3-hydroxypropionaldehyde hybrid system (HA-31M) against Pseudomonas aeruginosa.

[0068] Figure 25 shows the antibacterial effect of a mixture of 0.25% solution of 2-oxoacetate (CAA-21) and 0.25% solution of 3,3-diethoxy-1-propene (MAR-31) against Pseudomonas aeruginosa.

[0069] Figure 26 shows the antibacterial effect of a mixture of a 3% solution of 2-oxoacetic acid (CAA-21) and a 5% solution of 3-hydroxypropionaldehyde hybrid system (HA-31M) against Salmonella Typhimurium.

[0070] Figure 27 shows the antibacterial effect of a mixture of 0.5% solution of 2-oxoacetic acid (CAA-21) and 0.5% solution of 3,3-diethoxy-1-propene (MAR-31) against Salmonella Typhimurium.

[0071] Figure 28 shows the antibacterial effect of a mixture of a 5% solution of 2-oxoacetic acid (CAA-21) and a 5% solution of 3-hydroxypropionaldehyde hybrid system (HA-31M) against Salmonella Typhimurium.

[0072] Figure 29 shows the antibacterial effect of a mixture of a 1% solution of 2-oxoacetic acid (CAA-21) and a 1% solution of 3,3-diethoxy-1-propene (MAR-31) against Salmonella Typhimurium.

[0073] Figure 30 shows the antibacterial effects of mixtures of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5%, and 5%+5% solutions, respectively) against Escherichia coli.

[0074] Figure 31 shows the antibacterial effects of mixtures of 0.5% and 1% solutions of 2-oxoacetic acid (CAA-21) and 0.5% and 1% solutions of 3,3-diethoxy-1-propene (MAR-31) against Escherichia coli.

[0075] Figure 32 shows the antibacterial effects of mixtures of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5% and 5%+5% solutions, respectively) against Staphylococcus aureus.

[0076] Figure 33 shows the antibacterial effects of mixtures of 0.5% and 1% solutions of 2-oxoacetic acid (CAA-21) and 0.5% and 1% solutions of 3,3-diethoxy-1-propene (MAR-31) against Staphylococcus aureus.

[0077] Figure 34 shows the antibacterial effects of mixtures of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5%, and 5%+5% solutions, respectively) against Pseudomonas aeruginosa.

[0078] Figure 35 shows the antibacterial effects of mixtures of 0.5% and 1% solutions of 2-oxoacetate (CAA-21) and 0.5% and 1% solutions of 3,3-diethoxy-1-propene (MAR-31) against Pseudomonas aeruginosa.

[0079] Figure 36 shows the antibacterial effects of mixtures of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5%, and 5%+5% solutions, respectively) against Bacillus subtilis.

[0080] Figure 37 shows the antibacterial effects of mixtures of 0.5% and 1% solutions of 2-oxoacetic acid (CAA-21) and 0.5% and 1% solutions of 3,3-diethoxy-1-propene (MAR-31) against Bacillus subtilis.

[0081] Figure 38 shows the antibacterial effect of mixtures of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5%, and 5%+5% solutions, respectively) at all mixing ratios (compositions) in the case of disinfection efficacy against Bacillus subtilis spores.

[0082] Figure 39 shows the antibacterial effect of a mixture of a 2% solution of 2-oxoacetic acid (CAA-21) and a 2% solution of 3,3-diethoxy-1-propene (MAR-31) against Salmonella Typhimurium.

[0083] Figure 40 shows the antifungal effect of a mixture of a 1% solution of 2-oxoacetic acid (CAA-21) and a 1% solution of 3,3-diethoxy-1-propene (MAR-31) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0084] Figure 41 shows the antifungal effects of mixtures of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5%, and 5%+5% solutions, respectively) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

[0085] Figure 42 shows the antiviral effects of mixtures of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) (2%+4%, 3%+5% and 5%+5% solutions, respectively) against avian influenza virus MS96 / 1996 (H9N2).

[0086] Figure 43 shows the antiviral effect of a mixture of 0.05% solution of 2-oxoacetate (CAA-21) and 0.05% solution of 3,3-diethoxy-1-propene (MAR-31) against avian influenza virus MS96 / 1996 (H9N2).

[0087] The present invention is described illustratively by the following examples. However, the scope of the present invention should not be interpreted as being limited by the following examples. A person skilled in the art will be able to make various modifications and applications of the following examples.

[0088] 1. Preparation Example

[0089] Preparation of an antibacterial, antifungal, and antiviral composition containing 2-oxoacetate (CAA-21)

[0090] An antibacterial, antifungal, and antiviral composition containing 2-oxoacetic acid (CAA-21) was prepared according to the following reaction scheme 2.

[0091] [Reaction Equation 2]

[0092]

[0093] Specifically, 3 mmol of glyoxal of Formula 4, 0.036 mmol of concentrated hydrochloric acid, and 0.024 mmol of sodium nitrite were placed in a reaction vessel and heated at 70°C for 20 minutes. Subsequently, 1.5 mmol of concentrated nitric acid was added and heated at 70°C for 1.5 hours. Then, 0.3 mmol of 30% hydrogen peroxide was added and heated at 70°C for 2 hours. After the reaction was finished, 0.3 mmol of manganese dioxide was added and stirred until bubble generation stopped to remove residual hydrogen peroxide. After stirring for a certain period, the solids were removed by filtration, and a clear aqueous product was obtained. Additionally, a high concentration (50%) aqueous product [an antibacterial, antifungal, and antiviral composition containing 2-oxoacetic acid (CAA-21) of Formula 1] was obtained by low-pressure concentration in a concentrator.

[0094] Preparation of an antibacterial, antifungal, and antiviral composition comprising a 3-hydroxypropionaldehyde hybrid system (HA-31M)

[0095] An antibacterial, antifungal, and antiviral composition containing a 3-hydroxypropionaldehyde hybrid system (HA-31M) was prepared according to the following reaction scheme 3.

[0096] [Reaction Equation 3]

[0097]

[0098] Specifically, 135 mmol of 3,3-diethoxy-1-propanol of Formula 5 and 100 mL of 2N sulfuric acid were placed in a reaction vessel and stirred for 60 minutes at 5°C or below. After the reaction, 110 mmol of calcium carbonate was slowly added at the same temperature to neutralize the pH to a range of 6.0 to 7.0. The mixture was stirred for an additional 60 minutes at the same temperature. Subsequently, the solids were removed by vacuum filtration (~130 mbar) using a diaphragm pump, and a clear aqueous solution was obtained. Distilled water was added to the obtained aqueous solution to obtain 100 g of a product with a 10% concentration [an antibacterial, antifungal, and antiviral composition containing the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2].

[0099] 1 H-NMR (400 MHz, CD3CN) σ 9.70 (br S, 0.8H), 5.38 (d,J=8.0Hz, 0.2H), 5.22-5.28 (m, 0.2H), 5.06-5.15 (m, 0.06H), 5.02-5.05 (m, 0.10H), 4.80-4.88 (m, 0.22H), 4.68-4.74 (m, 0.42H), 3.95-4.05 (m, 0.49H), 3.75-3.85 (m, 2.01H), 3.62-3.74 (m, 0.64H), 3.48-3.60 (m, 7.46H), 3.44 (t, J=4Hz, 1.23H), 3.21-3.30 (m, 0.38H), 3.16 (t,J=4.0Hz, 3.69H), 2.55 (dt,J=8Hz, 4Hz, 2.7H),1.52-1.80 (m, 2.10H), 1.37-1.44 (m, 0.4H), 1.10 (t,J=6.0Hz, 9.8H).

[0100] GC-MS: HA-31 (Mw: 74) Found 74

[0101] Preparation of an antibacterial, antifungal, and antiviral composition containing 3,3-diethoxy-1-propene (MAR-31)

[0102] An antibacterial, antifungal, and antiviral composition containing 3,3-diethoxy-1-propene (MAR-31) was prepared according to the following reaction scheme 4.

[0103] [Reaction Equation 4]

[0104]

[0105] Specifically, 5 mmol of copper sulfate, 100 mmol of water, and 50 mmol of dimethyl sulfoxide (DMSO) were added to a reaction vessel, followed by the addition of 5 mmol of allyl bromide of Formula 6. Subsequently, the reaction product was heated at 100°C for 30 minutes, diluted with distilled water, and extracted with diethyl ether. The organic layer was collected, dried with calcium chloride, and allyl alcohol of Formula 7 was obtained by concentration under reduced pressure. Next, 4.80 mmol of pyridinium chlorochromate (PCC) and 6 ml of CH2Cl2 solution were added to the reaction vessel. The reaction solution was stirred at room temperature for 3 hours. After the reaction was complete, propenal of Formula 8 was obtained through a work-up process. Subsequently, by reacting in a diethyl ether solvent with ethanol and a p-toluenesulfonic acid (p-TsOH) catalyst, a final product [an antibacterial, antifungal, and antiviral composition containing 3,3-diethoxy-1-propene (MAR-31) of Formula 3] was obtained.

[0106] Preparation of a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M)

[0107] 2-oxoacetate (CAA-21) was diluted to 2%, 3%, and 5%, and 3-hydroxypropionaldehyde hybrid system (HA-31M) was diluted to 4% and 5%. Then, 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) were mixed in ratios of 3:1, 2:1, 1:1, 1:2, and 1:3 to prepare aqueous mixed solutions. The composition of the mixed solutions is presented in Table 1 below.

[0108]

[0109] Preparation of a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31)

[0110] 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) were diluted to concentrations of 0.05%, 0.25%, 0.5%, 1%, and 2%, respectively, and then aqueous mixed solutions were prepared by mixing 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) in ratios of 3:1, 2:1, 1:1, 1:2, and 1:3. The composition of the mixed solutions is presented in Table 2 below.

[0111]

[0112] Example 1: Evaluation of the biotic (disinfectant) activity of 2-oxoacetate (CAA-21) against harmful microorganisms

[0113] The results of the disinfection efficacy test against harmful bacteria (including spores), fungi, and viruses were expressed as the log reduction value of the target organism in the test group compared to the control group, and Table 3 below shows the evaluation criteria table for harmful microorganisms.

[0114]

[0115] Biocidal (disinfectant) activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against harmful bacteria (including spores)

[0116] To evaluate the bactericidal (disinfection) activity of glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) against harmful bacteria, tests were conducted according to the test for determining the effective dilution factor of disinfectants against bacteria, etc., in the guidelines for disinfectant efficacy testing notified by the Animal and Plant Quarantine Agency. Five bacterial strains [A: Salmonella Typhimurium (ACTC 13311), B: Escherichia coli (ACTC 1175), C: Staphylococcus aureus (ATCC 25923), D: Pseudomonas aeruginosa (ATCC 13388), E: Bacillus subtilis (ATCC 6633)] were inoculated into nutrient media (nutrient broth and trypricase soy broth) and cultured at 37°C for 16–22 hours. The bacterial concentration was 10 8 The concentration was maintained at CFU / ml or higher. Each medium was treated with control substances glutaraldehyde (GA) and 2-oxoacetate (CAA-21) at concentrations of 0.01%, 0.05%, 0.1%, 0.25%, 0.5%, 1%, and 2%, respectively, and the reaction was carried out at 4°C for 30 minutes. After the reaction, the medium was mixed with a neutralizing solution to eliminate the disinfectant activity. Subsequently, the neutralized reaction solution was inoculated into the medium and incubated at 37°C for 24 hours to measure the titer of the remaining bacteria. The disinfectant efficacy was evaluated by counting the number of remaining colonies after incubation.

[0117] As a result of evaluating the disinfection efficacy of glutaraldehyde (GA) at different concentrations (0.05%–2%) against Salmonella Typhimurium, excellent disinfection activity was observed at all concentrations (above 5 log reduction values) (see Fig. 1).

[0118] As a result of evaluating the disinfection efficacy of glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) against Salmonella Typhimurium at different concentrations (0.25%, 0.5%, 1%, 2%), glutaraldehyde (GA) showed excellent disinfection efficacy (greater than 5 log reduction values) at all concentrations, while 2-oxoacetic acid (CAA-21) showed good disinfection efficacy (greater than 1 log reduction value) at a concentration of 0.25% and excellent disinfection efficacy (greater than 5 log reduction values) at concentrations of 0.5% or higher. It exhibited a level of disinfection efficacy similar to that of the control substance, glutaraldehyde (GA) (see Figure 2).

[0119] As a result of evaluating the disinfection efficacy of 2-oxoacetic acid (CAA-21) at different concentrations (0.25%, 0.5%, 1%) against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis, the disinfection efficacy was good (above 1 log reduction value) for all tested strains at a concentration of 0.25%. At a concentration of 0.5%, the disinfection efficacy against Escherichia coli and Staphylococcus aureus was excellent (5 log reduction value or higher), and against Pseudomonas aeruginosa and Bacillus subtilis was excellent (3 log reduction value or higher). At a concentration of 1%, the disinfection efficacy against all tested strains was excellent (5 log reduction value or higher) (see Figure 4).

[0120] The 2% glutaraldehyde (GA) solution and the 2% oxoacetic acid (CAA-21) solution showed excellent performance (5 log reduction value or higher) against 5 test strains (see Fig. 6), and excellent sterilization activity against Bacillus subtilis (5 log reduction value or higher) (see Fig. 8).

[0121] Based on the above results, the evaluation results of the disinfection activity of each concentration of oxoacetic acid (CAA-21) solution against harmful bacteria (including spores) are summarized in Table 4 below.

[0122]

[0123] Biocide (disinfectant) activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against harmful fungi

[0124] To evaluate the disinfectant activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against harmful fungi, the "Fungal Agent Suspension Test Method - Fungi" (NIER-BP-E1-011) from the Biocide Efficacy Test Methods of the National Institute of Environmental Research was referenced. For biocides, testing under contamination conditions (3.0 g / L bovine serum albumin) is mandatory, and the three strains were as follows: X: Aspergillus brasiliensis (ATCC 16404), Y: Candida albicans (ATCC 10231), Z: Penicillium funiculosum (ATCC 11797). Prior to the test, fungal strains were cultured at 25°C for 5 days, and a suspension was prepared. The bactericidal substance was mixed with the suspension, and the reaction was carried out under contaminated conditions at 25°C for 5 minutes. Phosphate-buffered saline (PBS) was used as the control group instead of the test substance; after the reaction, the sample was serially diluted 10 times, plated onto Potato Dextrose Agar (PDA) medium, and incubated at 25°C for 5 days. The bactericidal activity was evaluated by checking the culture results and counting the number of colonies.

[0125] At a concentration of 0.01%, glutaraldehyde (GA) showed good disinfection efficacy against Aspergillus brasiliensis and Candida albicans (greater than 1 log reduction value) and very excellent disinfection efficacy against Penicillium funiculosum (greater than 4 log reduction values). At a concentration of 0.05% or higher, glutaraldehyde (GA) showed very excellent disinfection efficacy against all fungal strains (greater than 4 log reduction values) (see Fig. 14).

[0126] A 2% solution of 2-oxoacetic acid (CAA-21) was insufficient for disinfecting Aspergillus brasiliensis and Candida albicans (see Fig. 17).

[0127] Based on the above results, the evaluation results of the disinfection activity of glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) against harmful fungi are summarized in Table 5 below.

[0128]

[0129] Biocidal (disinfectant) activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against harmful viruses

[0130] The disinfectant activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against avian influenza virus MS96 / 1996 (H9N2) was evaluated. The evaluation method was conducted in accordance with the test for determining effective dilution factors of virus disinfectants within the guidelines for disinfectant efficacy testing notified by the Animal and Plant Quarantine Agency. After mixing the subcultured virus suspension with hard water, equal amounts of the control substances glutaraldehyde (GA) and 2-oxoacetate (CAA-21) were reacted at 4°C for 30 minutes. After the reaction, the mixture was mixed with a neutralizing agent to eliminate the disinfectant activity. After neutralization, decimal subdilution was performed, and the reaction solution was inoculated into the allantral cavities of five hatching eggs for each dilution factor and incubated at 37°C for 120 hours. After incubation, the allantral fluid was extracted, and an HA test was performed using chicken RBCs to calculate the titer of the remaining virus.

[0131] Glutaraldehyde (GA) showed excellent disinfection efficacy (greater than 3 log reduction values) at a concentration of 0.01%, and 2-oxoacetic acid (CAA-21) showed good disinfection efficacy (greater than 1 log reduction value) at a concentration of 0.01%. Both glutaraldehyde (GA) and 2-oxoacetic acid (CAA-21) showed excellent disinfection efficacy (greater than 5 log reduction values) at concentrations of 0.05% or higher (see Fig. 19).

[0132] Based on the above results, the evaluation results of the disinfection activity of glutaraldehyde (GA) and 2-oxoacetate (CAA-21) against harmful viruses are summarized in Table 6 below.

[0133]

[0134] Example 2: Evaluation of the Biocidal (Disinfectant) Activity of the 3-Hydroxypropionaldehyde Hybrid System (HA-31M) Against Harmful Microorganisms

[0135] The results of the disinfection efficacy test against harmful bacteria (including spores), fungi, and viruses were expressed as the log reduction value of the target organism in the test group compared to the control group, and Table 7 below shows the evaluation criteria table for harmful microorganisms.

[0136]

[0137] Biocidal (disinfectant) activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful bacteria (including spores)

[0138] To evaluate the bactericidal (disinfection) activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful bacteria, a test was conducted in accordance with the test for determining the effective dilution factor of disinfectants against bacteria, etc., within the guidelines for disinfectant efficacy testing notified by the Animal and Plant Quarantine Agency. Five bacterial strains [A: Salmonella Typhimurium (ACTC 13311), B: Escherichia coli (ACTC 1175), C: Staphylococcus aureus (ATCC 25923), D: Pseudomonas aeruginosa (ATCC 13388), E: Bacillus subtilis (ATCC 6633)] were inoculated into nutrient media (nutrient broth and trypricase soy broth) and cultured at 37°C for 16–22 hours. The bacterial concentration was 10 8 The CFU / ml level was maintained above 0.5%, 1%, 2%, and 2.5% of the control substances, glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M), were treated in each medium, and the reaction was carried out at 4°C for 30 minutes. After the reaction, the medium was mixed with a neutralizing solution to eliminate the disinfectant activity. Subsequently, the neutralized reaction solution was inoculated into the medium to measure the titer of the remaining bacteria, and the medium was incubated at 37°C for 24 hours. The disinfectant efficacy was evaluated by counting the number of remaining colonies after incubation.

[0139] As a result of evaluating the disinfection efficacy of glutaraldehyde (GA) at different concentrations (0.05%–2%) against Salmonella Typhimurium, excellent disinfection activity was observed at all concentrations (above 5 log reduction values) (see Fig. 1).

[0140] As a result of evaluating the disinfection efficacy of glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against Salmonella Typhimurium at different concentrations (0.5%, 1%, 2%, 2.5%), glutaraldehyde (GA) showed excellent disinfection efficacy at all concentrations (5 log reduction value or higher), while the 3-hydroxypropionaldehyde hybrid system (HA-31M) showed insufficient disinfection efficacy at all concentrations (less than 1 log reduction value). It exhibited relatively lower disinfection efficacy compared to the control substance, glutaraldehyde (GA) (see Figure 3).

[0141] As a result of evaluating the disinfection efficacy of the 3-hydroxypropionaldehyde hybrid system (HA-31M) at different concentrations (0.5%, 1%, 2%, 2.5%) against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis, at a concentration of 0.5%, the disinfection efficacy against Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis was insufficient (less than 1 log reduction value), while the disinfection efficacy against Escherichia coli was good (1 log reduction value ...and so on. At a 1% concentration, the disinfection efficacy against Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis was insufficient (less than 1 log reduction value), while the disinfection efficacy against Escherichia coli was good (more than 1 log reduction value). At a 2% concentration, the disinfection efficacy against Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis was insufficient (less than 1 log reduction value), while the disinfection efficacy against Escherichia coli was good (more than 1 log reduction value). 2.At a concentration of 5%, the disinfection efficacy against Escherichia coli and Staphylococcus aureus was good (1 log reduction value or more), and the disinfection efficacy against Pseudomonas aeruginosa and Bacillus subtilis was excellent (3 log reduction value or more) (see Fig. 5).

[0142] The 2% glutaraldehyde (GA) solution showed excellent performance (5 log reduction values ​​or higher) against 5 test strains, and the 2% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution showed good disinfection efficacy against Escherichia coli (1 log reduction value or higher), but insufficient disinfection efficacy (less than 1 log reduction value) against 4 other strains (see Fig. 7). In addition, the 3-hydroxypropionaldehyde hybrid system (HA-31M) showed insufficient sterilization activity (less than 1 log reduction value) against Bacillus subtilis spores (see Fig. 9).

[0143] Based on the above results, the evaluation results of the disinfection activity of each concentration of 3-hydroxypropionaldehyde hybrid system (HA-31M) solution against harmful bacteria (including spores) are summarized in Table 8 below.

[0144]

[0145] Biocide (disinfectant) activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful fungi

[0146] To evaluate the disinfection activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful fungi, the "Fungiicide Suspension Test Method - Fungi" (NIER-BP-E1-011) from the National Institute of Environmental Research's Biocide Efficacy Test Methods was referenced. For biocides, testing under contamination conditions (3.0 g / L bovine serum albumin) is mandatory, and the three strains were as follows: X: Aspergillus brasiliensis (ATCC 16404), Y: Candida albicans (ATCC 10231), Z: Penicillium funiculosum (ATCC 11797). Prior to the test, fungal strains were cultured at 25°C for 5 days, and a suspension was prepared. The suspension was then mixed with the bactericidal test substance, and the reaction was carried out under contaminated conditions at 25°C for 5 minutes. PBS was used as the control group instead of the test substance; after the reaction, the sample was serially diluted 10 times, plated onto Potato Dextrose Agar (PDA) medium, and incubated at 25°C for 5 days. The bactericidal activity was evaluated by checking the culture results and counting the number of colonies.

[0147] Glutaraldehyde (GA) showed excellent disinfection efficacy (greater than 4 log reduction value) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum at concentrations of 0.5% to 2.5% (see Fig. 15).

[0148] The 3-hydroxypropionaldehyde hybrid system (HA-31M) showed insufficient disinfection efficacy against Aspergillus brasiliensis (less than 1 log reduction value) only at a concentration of 0.5%, and excellent (3 log reduction value) to very excellent (4 log reduction value) disinfection efficacy against Candida albicans and Penicillium funiculosum at a concentration of 1–2.5% (see Fig. 16).

[0149] Based on the above results, the evaluation results of the disinfection activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful fungi are summarized in Table 9 below.

[0150]

[0151] Biocidal (disinfectant) activity of glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful viruses

[0152] The disinfectant activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against avian influenza virus MS96 / 1996 (H9N2) was evaluated. The evaluation method was conducted in accordance with the test for determining the effective dilution factor of virus disinfectants within the guidelines for disinfectant efficacy testing notified by the Animal and Plant Quarantine Agency. After mixing the subcultured virus suspension with hard water, equal amounts of the control substance glutaraldehyde (GA) and the 3-hydroxypropionaldehyde hybrid system (HA-31M) were reacted at 4°C for 30 minutes. After the reaction, the mixture was mixed with a neutralizing agent to eliminate the disinfectant activity. After neutralization, decimal subdilution was performed, and the reaction solution was inoculated into the allantral cavities of five hatching eggs for each dilution factor and incubated at 37°C for 120 hours. After incubation, the allantral fluid was extracted, and the HA test was performed using chicken RBCs to calculate the titer of the remaining virus.

[0153] Glutaraldehyde (GA) showed excellent disinfection efficacy at a concentration of 0.01% (greater than 3 log reduction value) and excellent disinfection efficacy at a concentration of 0.05% or higher (greater than 4 log reduction value). The 3-hydroxypropionaldehyde hybrid system (HA-31M) showed excellent disinfection efficacy at concentrations of 1% and 2% (greater than 4 log reduction value) (see Fig. 20).

[0154] Based on the above results, the evaluation results of the disinfection activity of the glutaraldehyde (GA) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful viruses are summarized in Table 10 below.

[0155]

[0156] Example 3: Evaluation of the biotic (disinfectant) activity of a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful microorganisms

[0157] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful bacteria (including spores)

[0158] The disinfection activity against five types of bacteria was evaluated according to the composition of 2-oxoacetate (CAA-21):3-hydroxypropionaldehyde hybrid system (HA-31M) in a mixed solution of 2-oxoacetate (CAA-21) solution and 3-hydroxypropionaldehyde hybrid system (HA-31M). The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) instead of 2-oxoacetate (CAA-21).

[0159] The disinfection efficacy against Salmonella Typhimurium was confirmed according to the composition of a mixture of 2% 2-oxoacetate (CAA-21) and 4% 3-hydroxypropionaldehyde hybrid system (HA-31M). The disinfection efficacy of mixtures with ratios of 2-oxoacetate (CAA-21):3-hydroxypropionaldehyde hybrid system (HA-31M) of 3:1, 2:1, 1:1, 1:2, and 1:3 was excellent (above 5 log reduction values) (see Fig. 22). In terms of disinfectant efficacy against Pseudomonas aeruginosa, all compositions of the mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde (HA-31M) were excellent (5 log reduction value) (see Fig. 24).

[0160] The disinfection efficacy against Salmonella Typhimurium was confirmed according to the mixed composition of a mixed solution of 3% 2-oxoacetic acid (CAA-21) solution and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution and a mixed solution of 5% 2-oxoacetic acid (CAA-21) solution and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution. In terms of disinfection efficacy against Salmonella Typhimurium, mixed solutions of 3% 2-oxoacetic acid (CAA-21) solution and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M) in 3:1, 2:1, 1:1, 1:2, and 1:3 ratios showed excellent disinfection efficacy (greater than 5 log reduction values) (see Fig. 26).

[0161] A mixed solution of 5% 2-oxoacetic acid (CAA-21) solution and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 28).

[0162] In terms of disinfection efficacy against Escherichia coli, the mixed solution of 2-oxoacetate (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, the mixed solution of 3-oxoacetate (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and the mixed solution of 5-oxoacetate (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 30).

[0163] In terms of disinfection efficacy against Staphylococcus aureus, the mixed solution of 2-oxoacetate (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, the mixed solution of 3-oxoacetate (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and the mixed solution of 5-oxoacetate (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 32).

[0164] In terms of disinfection efficacy against Pseudomonas aeruginosa, the disinfection efficacy was excellent (greater than 5 log reduction value) at all mixing ratios (compositions) for the mixed solution of 2-oxoacetate (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, the mixed solution of 3-oxoacetate (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and the mixed solution of 5-oxoacetate (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution (see Fig. 34).

[0165] In terms of disinfection efficacy against Bacillus subtilis, the mixed solution of 2-oxoacetic acid (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, the mixed solution of 3-oxoacetic acid (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and the mixed solution of 5-oxoacetic acid (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 36).

[0166] In terms of disinfection efficacy against Bacillus subtilis spores, the mixed solution of 2-oxoacetate (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, the mixed solution of 3-oxoacetate (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and the mixed solution of 5-oxoacetate (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution showed excellent disinfection efficacy (greater than 3 log reduction value) at all mixing ratios (compositions) (see Fig. 38).

[0167] Based on the above results, the results of the evaluation of the disinfection activity of a mixture of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful bacteria (including spores) at different concentrations are summarized in Table 11 below.

[0168]

[0169] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful fungi

[0170] Disinfectant activity against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum was evaluated according to the composition (mixing ratio) of a mixed solution of 2-oxoacetic acid (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, a mixed solution of 3-oxoacetic acid (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and a mixed solution of 5-oxoacetic acid (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution. The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) instead of 2-oxoacetate (CAA-21).

[0171] A mixed solution of 2-oxoacetic acid (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution showed good disinfection efficacy (1 log reduction value or more) at a composition (mixing ratio) of 3:1, and excellent disinfection efficacy (3 log reduction value or more) or very excellent (4 log reduction value or more) at all other compositions (mixing ratios) (see Fig. 41).

[0172] Based on the above results, the results of the evaluation of the disinfection activity of mixed solutions against harmful fungi according to the concentration and composition (mixing ratio) of the mixture of 2-oxoacetic acid (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) are summarized in Table 12 below.

[0173]

[0174] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) against harmful viruses

[0175] Disinfection activity against avian influenza virus MS96 / 1996 (H9N2) was evaluated according to the composition (mixing ratio) of a mixed solution of 2-oxoacetic acid (CAA-21) 2% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 4% solution, a mixed solution of 3-oxoacetic acid (CAA-21) 3% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution, and a mixed solution of 5-oxoacetic acid (CAA-21) 5% solution and 3-hydroxypropionaldehyde hybrid system (HA-31M) 5% solution. The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetate (CAA-21) and 3-hydroxypropionaldehyde hybrid system (HA-31M) instead of 2-oxoacetate (CAA-21).

[0176] The mixed solution of 2% 2-oxoacetic acid (CAA-21) and 4% 3-hydroxypropionaldehyde hybrid system (HA-31M), the mixed solution of 3% 2-oxoacetic acid (CAA-21) and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M), and the mixed solution of 5% 2-oxoacetic acid (CAA-21) and 5% 3-hydroxypropionaldehyde hybrid system (HA-31M) showed excellent disinfection efficacy (greater than 4 log reduction value) in all compositions (see Fig. 42).

[0177] Based on the above results, the disinfection activity results against avian influenza virus MS96 / 1996 (H9N2) according to the composition (mixing ratio) of a mixed solution of 0.05% 2-oxoacetic acid (CAA-21) solution and 0.05% 3-hydroxypropionaldehyde hybrid system (HA-31M) solution are summarized in Table 13 below.

[0178]

[0179] Example 4: Evaluation of the Biocidal (Disinfectant) Activity of 3,3-Diethoxy-1-Profen (MAR-31) Against Harmful Microorganisms

[0180] Disinfectant activity of 3,3-diethoxy-1-propene (MAR-31) against harmful bacteria (including spores)

[0181] The evaluation method was the same as in Example 1, but the experiment was conducted using 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetate (CAA-21).

[0182] The disinfection efficacy of the 0.25% solution of 3,3-diethoxy-1-propene (MAR-31) against Salmonella Typhimurium was insufficient (less than 1 log reduction value), and the disinfection efficacy of the 0.5% solution was good (more than 1 log reduction value). The disinfection efficacy of the 1% and 2% solutions was excellent (more than 5 log reduction values) (see Fig. 10).

[0183] In the case of 3,3-diethoxy-1-propene (MAR-31), at a concentration of 0.25%, the disinfection efficacy against Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis was good (1 log reduction value or more), and at a concentration of 0.5%, the disinfection efficacy against Pseudomonas aeruginosa and Bacillus subtilis was very excellent (4 log reduction value or more). At a concentration of 0.25%, the disinfection efficacy against Escherichia coli was excellent (greater than 5 log reduction values), and at a concentration of 0.5%, against Staphylococcus aureus; at a concentration of 1%, the disinfection efficacy against all tested fungal strains was excellent (greater than 5 log reduction values) (see Fig. 11). The 2% solution showed excellent disinfection efficacy (greater than 5 log reduction values) against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa (see Fig. 12). However, the disinfection efficacy against the spores of Bacillus subtilis was insufficient (less than 1 log reduction value) (see Fig. 13).

[0184] Based on the above results, the evaluation results of the disinfection activity of 3,3-diethoxy-1-propene (MAR-31) against harmful bacteria (including spores) at different concentrations are summarized in Table 14 below.

[0185]

[0186] Disinfectant activity of 3,3-diethoxy-1-propene (MAR-31) against harmful fungi

[0187] The evaluation method was the same as in Example 1, but the experiment was conducted using 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetate (CAA-21).

[0188] 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfection efficacy (4 log reduction value or higher) against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum at all concentrations (0.01%–2%) (see Fig. 18).

[0189] Based on the above results, the evaluation results of the disinfection activity of 3,3-diethoxy-1-propene (MAR-31) against harmful fungi at different concentrations are summarized in Table 15 below.

[0190]

[0191] Disinfectant activity of 3,3-diethoxy-1-propene (MAR-31) against harmful viruses

[0192] The evaluation method was the same as in Example 1, but the experiment was conducted using 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetate (CAA-21).

[0193] 3,3-diethoxy-1-propene (MAR-31) showed good disinfection efficacy (1 log reduction value or higher) at a concentration of 0.01% and excellent disinfection efficacy (5 log reduction values ​​or higher) at a concentration of 0.05% or higher (see Fig. 21).

[0194] Based on the above results, the evaluation results of the disinfection activity of 3,3-diethoxy-1-propene (MAR-31) against harmful viruses at different concentrations are summarized in Table 16 below.

[0195]

[0196] Example 5: Evaluation of the biotic (disinfectant) activity of a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) against harmful microorganisms

[0197] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) against harmful bacteria (including spores)

[0198] The disinfectant activity against Salmonella Typhimurium and Pseudomonas aeruginosa was evaluated according to the composition of 2-oxoacetate (CAA-21):3,3-diethoxy-1-propene (MAR-31) in a mixed solution of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31). The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetate (CAA-21).

[0199] The disinfection efficacy against Salmonella Typhimurium was confirmed according to the composition of a 0.25% solution mixture of 2-oxoacetic acid (CAA-21) and 3,3-diethoxy-1-propene (MAR-31). Mixtures with mixing ratios of 2-oxoacetate (CAA-21):3,3-diethoxy-1-propene (MAR-31) of 3:1, 2:1, and 1:1 and 2-oxoacetate (CAA-21) showed good results (above 1 log reduction value), while mixtures with mixing ratios of 2-oxoacetate (CAA-21):3,3-diethoxy-1-propene (MAR-31) of 1:2 and 1:3 and 3,3-diethoxy-1-propene (MAR-31) showed poor results (below 1 log reduction value) (see Fig. 23).

[0200] Regarding the disinfection efficacy against Pseudomonas aeruginosa, all compositions of the mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) showed good to excellent results (2 log reduction value ~ 4 log reduction value), and it was confirmed that the mixture exhibited a synergistic effect with superior disinfection activity compared to 0.25% single solutions of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) (see Fig. 25).

[0201] The disinfection efficacy against Salmonella Typhimurium was confirmed according to the mixed composition of a 0.5% solution of 2-oxoacetic acid (CAA-21) and a 0.5% solution of 3,3-diethoxy-1-propene (MAR-31), and a 1% solution of 2-oxoacetic acid (CAA-21) and a 1% solution of 3,3-diethoxy-1-propene (MAR-31).

[0202] Regarding the disinfection efficacy against Salmonella Typhimurium, the 3:1 and 2:1 mixed solutions of 0.5% 2-oxoacetate (CAA-21) and 0.5% 3,3-diethoxy-1-propene (MAR-31), and the 0.5% 2-oxoacetate (CAA-21) solution showed excellent disinfection efficacy (greater than 5 log reduction values). The 1:1, 1:2, and 1:3 mixed solutions, and the 0.5% 3,3-diethoxy-1-propene (MAR-31) solution showed excellent efficacy (greater than 3 log reduction values) (see Fig. 27). The disinfecting efficacy of the 1% solution of 2-oxoacetic acid (CAA-21) was excellent (greater than 5 log reduction), and the 1% solution of 3,3-diethoxy-1-propene (MAR-31) was good (greater than 1 log reduction). The mixed solution of the 1% solution of 2-oxoacetic acid (CAA-21) and the 1% solution of 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfecting efficacy (greater than 5 log reduction) at all mixing ratios (compositions) (see Fig. 29).

[0203] In terms of disinfection efficacy against Escherichia coli, the mixed solution of 0.5% 2-oxoacetate (CAA-21) and 0.5% 3,3-diethoxy-1-propene (MAR-31), and the mixed solution of 1% 2-oxoacetate (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 31).

[0204] Regarding the disinfectant efficacy against Staphylococcus aureus, the mixed solution of 0.5% 2-oxoacetate (CAA-21) and 0.5% 3,3-diethoxy-1-propene (MAR-31) at a mixing ratio of 3:1 was excellent (greater than 3 log reduction), while the other compositions were superior (greater than 5 log reduction). The mixed solution of 1% 2-oxoacetate (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) was superior (greater than 5 log reduction) in all compositions (see Fig. 33).

[0205] Regarding the disinfection efficacy against Pseudomonas aeruginosa, the mixed solution of 0.5% 2-oxoacetate (CAA-21) and 0.5% 3,3-diethoxy-1-propene (MAR-31) at a mixing ratio of 1:1 was excellent (greater than 5 log reduction), while the other compositions were excellent (greater than 3 log reduction). The mixed solution of 1% 2-oxoacetate (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfection efficacy (greater than 5 log reduction) at all mixing ratios (compositions) (see Fig. 35).

[0206] Regarding the disinfectant efficacy against Bacillus subtilis, a mixed solution of 0.5% 2-oxoacetate (CAA-21) and 0.5% 3,3-diethoxy-1-propene (MAR-31) with a mixing ratio of 3:1 was excellent (greater than 3 log reduction values), while the remaining compositions were superior (greater than 5 log reduction values). A mixed solution of 1% 2-oxoacetate (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) was superior (greater than 5 log reduction values) in all compositions (see Fig. 37).

[0207] In terms of disinfection efficacy against Salmonella Typhimurium, a mixed solution of 2% 2-oxoacetic acid (CAA-21) and 2% 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfection efficacy (greater than 5 log reduction value) at all mixing ratios (compositions) (see Fig. 39).

[0208] In terms of sterilization efficacy against Bacillus subtilis spores, a mixed solution of 2% 2-oxoacetic acid (CAA-21) and 2% 3,3-diethoxy-1-propene (MAR-31) showed good disinfection efficacy (greater than 1 log reduction value) at all mixing ratios (compositions).

[0209] Based on the above results, the results of the evaluation of the disinfection activity of a mixture of 2-oxoacetic acid (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) against harmful bacteria (including spores) at different concentrations are summarized in Table 17 below.

[0210]

[0211] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) against harmful fungi

[0212] The disinfectant activity against Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum was evaluated according to the composition (mixing ratio) of a mixed solution of 1% 2-oxoacetic acid (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31). The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetic acid (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetic acid (CAA-21).

[0213] A mixed solution of 1% 2-oxoacetic acid (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) with a mixing ratio of 2:1 showed excellent disinfection efficacy against Candida albicans (greater than 3 log reduction value), and a mixed solution of the remaining composition showed very excellent disinfection efficacy (greater than 4 log reduction value) (see Fig. 40).

[0214] Based on the above results, the evaluation results of the disinfection activity of a mixed solution of 1% 2-oxoacetic acid (CAA-21) and 1% 3,3-diethoxy-1-propene (MAR-31) against harmful fungi are summarized in Table 18 below.

[0215]

[0216] Disinfectant activity of a mixture of 2-oxoacetate (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) against harmful viruses

[0217] Disinfectant activity against avian influenza virus MS96 / 1996 (H9N2) was evaluated according to the composition (mixing ratio) of a mixed solution of 0.05% 2-oxoacetic acid (CAA-21) solution and 0.05% 3,3-diethoxy-1-propene (MAR-31) solution. The evaluation method was the same as in Example 1, but the experiment was conducted using a mixture of 2-oxoacetic acid (CAA-21) and 3,3-diethoxy-1-propene (MAR-31) instead of 2-oxoacetic acid (CAA-21).

[0218] A mixed solution of 0.05% 2-oxoacetic acid (CAA-21) and 0.05% 3,3-diethoxy-1-propene (MAR-31) showed excellent disinfection efficacy (greater than 4 log reduction value) in all compositions (see Fig. 43).

[0219] Based on the above results, the disinfection activity results against avian influenza virus MS96 / 1996 (H9N2) according to the composition (mixing ratio) of a mixed solution of 0.05% 2-oxoacetic acid (CAA-21) solution and 0.05% 3,3-diethoxy-1-propene (MAR-31) solution are summarized in Table 19 below.

[0220]

Claims

1. An antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid of Formula 1 (CAA-21), 3-hydroxypropionaldehyde hybrid system of Formula 2 (HA-31M), 3,3-diethoxy-1-propene of Formula 3 (MAR-31), or a mixture thereof. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] 2. In Paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antibacterial activity against one or more bacteria selected from the group consisting of Salmonella Typhimurium, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis, and their spores.

3. In Paragraph 2, The above composition is an antibacterial, antifungal, and antiviral composition having sterilizing activity against Bacillus subtilis spores.

4. In Paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antifungal activity against one or more fungi selected from the group consisting of Aspergillus brasiliensis, Candida albicans, and Penicillium funiculosum.

5. In Paragraph 1, The above composition is an antibacterial, antifungal, and antiviral composition having antiviral activity against avian influenza virus MS96 / 1996 (H9N2).

6. In Paragraph 1, An antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21) of the above chemical formula 1, wherein the composition is a 0.01% to 5% aqueous solution.

7. In Paragraph 1, An antibacterial, antifungal, and antiviral composition comprising the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Chemical Formula 2 above is an aqueous solution of 0.5% to 5%.

8. In Paragraph 1, An antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of the above chemical formula 3, wherein the composition is a 0.01% to 2% aqueous solution.

9. In Paragraph 1, A composition for antibacterial, antifungal, and antiviral properties, wherein the mixture of 2-oxoacetic acid (CAA-21) of Formula 1 and 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2, the mixture of 2-oxoacetic acid (CAA-21) of Formula 1 and 3,3-diethoxy-1-propene (MAR-31) of Formula 3, and the mixture of 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2 and 3,3-diethoxy-1-propene (MAR-31) of Formula 3 are each mixed in a ratio of 3:1 to 1:

3.

10. A method for preparing an antibacterial, antifungal, and antiviral composition comprising 2-oxoacetic acid (CAA-21) of the following chemical formula 1, wherein (a) a step of placing glyoxal of the following chemical formula 4 into a reaction vessel with concentrated hydrochloric acid (c-HCl) and sodium nitrite (NaNO2) and heating; (b) adding concentrated nitric acid (HNO3) to the reaction product of step (a) and heating; (c) a step of adding hydrogen peroxide (H2O2) to the reaction product of step (b) and heating, adding manganese dioxide (MnO2) and stirring until bubble generation stops after the reaction is finished, and then removing the remaining hydrogen peroxide; and (d) a method comprising the step of stirring the reaction product of step (c) above, removing solids by filtration to obtain a product in the form of a clear aqueous solution, and further obtaining a final aqueous solution product of high concentration (50%) [2-oxoacetic acid (CAA-21) of Formula 1 below] by low-pressure concentration in a concentrator. [Chemical Formula 1] [Chemical Formula 4] 11. A method for preparing an antibacterial, antifungal, and antiviral composition comprising a 3-hydroxypropionaldehyde hybrid system (HA-31M) of the following chemical formula 2, wherein (a) a step of adding 3,3-diethoxy-1-propanol of the following chemical formula 5 and 2N H2SO4 to a reaction vessel and stirring for 60 minutes at 5°C or lower to terminate the reaction; (b) adding CaCO3 to the solution obtained in step (a) and adjusting the pH to neutral 6.0-7.5; and (c) a method comprising the step of stirring the solution obtained in step (b) at 5°C or lower for 60 minutes, then filtering the reaction solution under reduced pressure using a diaphragm pump (~130 mbar) to obtain a mixture, and then diluting the resulting mixture with distilled water to a concentration of 10% to obtain a final product in the form of an aqueous solution of Formula 2 below [an antibacterial, antifungal, and antiviral composition comprising the 3-hydroxypropionaldehyde hybrid system (HA-31M) of Formula 2 below]. [Chemical Formula 2] [Chemical Formula 5] 12. A method for preparing an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of the following chemical formula 3, wherein (a) a step of adding copper sulfate (CuSO4), water, and dimethyl sulfoxide (DMSO) to a reaction vessel, adding allyl bromide of the following chemical formula 6, heating the reaction mixture, diluting it with distilled water, extracting it with diethyl ether, collecting the organic layer, drying it with calcium chloride (CaCl2), and concentrating it under reduced pressure to obtain allyl alcohol of the following chemical formula 7; (b) a step of adding pyridinium chlorochromate (PCC) and CH2Cl2 to a reaction vessel, adding the allyl alcohol of Formula 7 obtained in step (a) and CH2Cl2 under stirring, and stirring at room temperature until the reaction is complete, thereby obtaining propenal of Formula 8; and (c) a method comprising the step of reacting the propenal of Formula 8 obtained in step (b) above with ethanol and a catalyst of p-toluenesulfonic acid (PTSA, p-TsOH) in a diethyl ether solvent to obtain a final product in the form of a clear aqueous solution [an antibacterial, antifungal, and antiviral composition comprising 3,3-diethoxy-1-propene (MAR-31) of Formula 3 below]. [Chemical Formula 3] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8]

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