Antibacterial or antiviral agent

Abstract

The purpose of the present disclosure is to provide a novel antibacterial or antiviral agent capable of imparting an antibacterial or antiviral effect on a space, an article, a human body, or the like. An antibacterial or antiviral agent according to the present disclosure is characterized by containing at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexene-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane.

Description

antibacterial or antiviral agents

[0001] The present disclosure relates to an antibacterial or antiviral agent that can impart an antibacterial or antiviral effect to a space, an object, the human body, etc.

[0002] Since bacterial proliferation and viruses can cause deterioration of the living environment, decay, infection, etc., measures against them are taken using antibacterial or antiviral agents. Most conventional antibacterial or antiviral agents are non-volatile, but volatile agents are also known.

[0003] Non-volatile antibacterial or antiviral agents must be directly attached to or contained in an object before use, whereas volatile antibacterial or antiviral agents can be simply placed in the target space or the space where the object is located and allowed to volatilize, allowing the antibacterial or antiviral effect to spread to every corner of the target space or object, making them superior in terms of ease of use.

[0004] Previously, volatile antibacterial agents reported include diacetyl, thymol, trans-2-hexenal, trans-2-hexenyl acetate, linalool, 1,8-cineole, acetoin (see Patent Document 1), 2-methylpropanoic acid 2,2-dimethyl-1-(2-hydroxy-1-methylethyl)propyl ester or a derivative thereof (see Patent Document 2), and capillin (Patent Document 3). In recent years, awareness of measures against infectious diseases and cleanliness has increased, and there is a demand for further development of antibacterial or antiviral agents.

[0005] JP 2001-29054 A JP 2016-44153 A JP 2015-39353 A

[0006] An object of the present disclosure is to provide a new antibacterial or antiviral agent that can impart antibacterial or antiviral effects to spaces, objects, the human body, etc.

[0007] The present inventors conducted extensive research to solve the above problems and found that 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane have excellent antibacterial or antiviral effects and can be used as antibacterial or antiviral agents. The present inventors also found that these compounds are volatile and can impart antibacterial or antiviral effects to a target object even in a volatilized state. The present invention was completed based on these findings and through further research.

[0008] That is, the present disclosure provides the following aspects of the invention. Item 1. An antibacterial or antiviral agent comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane. Item 2. An antibacterial or antiviral composition for use in space, comprising the antibacterial or antiviral agent according to Item 1 and a solvent. Item 3. An antibacterial or antiviral composition for use in an article, comprising the antibacterial or antiviral agent according to Item 1 and a solvent. Item 4. The antibacterial or antiviral composition for use in an article according to Item 3, wherein the article is a textile product. Item 5. The antibacterial or antiviral composition for use in an article according to Item 3, wherein the article has a hard surface. Item 6. Item 6. Use of at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane for antibacterial or antiviral purposes in a space or an article. Item 7. Use of a composition comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane, and a solvent, for antibacterial or antiviral purposes in a space or an article. Item 8. Use of a composition comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane, and a solvent, as an antibacterial or antiviral composition for use in a space. Item 9. Item 10. Use of a composition comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane, and a solvent, as an antibacterial or antiviral composition for an article. Item 11. The use according to Item 9, wherein the article is a textile product. Item 12. The use according to Item 9, wherein the article has a hard surface.Item 12. An antibacterial or antiviral method for treating an object for which antibacterial or antiviral properties are desired using at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane. Item 13. An antibacterial or antiviral method for treating an object for which antibacterial or antiviral properties are desired using a composition comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane, and a solvent. Item 14. The method of Item 12 or 13, wherein the object for which antibacterial or antiviral properties are desired is a space, and the space is treated with the compound or composition. Item 15. The method of Item 12 or 13, wherein the object for which antibacterial or antiviral properties are desired is an article, and the article is treated with the compound or composition. Item 16. The method according to Item 15, wherein the article is a textile product. Item 17. The method according to Item 15, wherein the article is an article having a hard surface. Item 18. Use of at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane for the manufacture of an antibacterial or antiviral composition.

[0009] According to the present disclosure, a novel antibacterial or antiviral agent is provided. Furthermore, by volatilizing the antibacterial or antiviral agent of the present disclosure in a space, it is possible to impart antibacterial or antiviral effects not only to the space but also to objects present in the space and components that separate the space, thereby making it possible to create a hygienic living space in a simple manner and reducing the risk of contracting an infectious disease. Furthermore, because bacteria present in living spaces are also a cause of bad odors, the antibacterial or antiviral agent of the present disclosure can prevent or remove bad odors, creating a comfortable living space.

[0010] 1. Definitions In the present disclosure, the notation "X to Y" regarding a numerical range indicates a numerical range of not less than X and not more than Y.

[0011] In the present disclosure, volatile means volatilizing at room temperature and normal pressure (20°C, 1 atmosphere).

[0012] In this disclosure, "antibacterial" refers to reducing bacterial activity, resulting in the killing of bacteria or the inhibition of bacterial growth. Also, in this disclosure, "antiviral" refers to reducing viral activity, resulting in a decrease in the number of viruses or a decrease in viral infectivity. In this disclosure, "antibacterial" or "antiviral" refers to a substance used for antibacterial or antiviral purposes.

[0013] In the present disclosure, an antibacterial or antiviral composition for space refers to a composition that is used by treating a space with an antibacterial or antiviral agent for the purpose of making the space antibacterial or antiviral.

[0014] In this disclosure, an antibacterial or antiviral composition for an article refers to a composition used by treating an article with an antibacterial or antiviral agent for the purpose of providing the article with antibacterial or antiviral properties.

[0015] In this disclosure, topical antibacterial or antiviral compositions refer to compositions that are applied to the skin for antibacterial or antiviral use.

[0016] In the present disclosure, an antibacterial or antiviral method refers to a method of imparting an antibacterial or antiviral effect to a subject for which antibacterial or antiviral effect is desired.

[0017] In the present disclosure, a hard surface refers to the surface of a hard member such as resin, ceramic, or glass.

[0018] 2. Antibacterial or Antiviral Agent The antibacterial or antiviral agent of the present disclosure is characterized by containing, as an active ingredient, at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane. The antibacterial or antiviral agent of the present disclosure is described in detail below.

[0019] [Active ingredient] The antibacterial or antiviral agent of the present disclosure contains, as an active ingredient, at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane. All of the compounds are volatile compounds.

[0020] In the antibacterial or antiviral agent of the present disclosure, one active ingredient may be selected from 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane and used alone, or two or more active ingredients may be used in combination.

[0021] Of the above compounds, 3-methyl-1-pentanol and 2,5-dimethylfuran are preferred from the viewpoint of exhibiting superior antibacterial activity against synthetic resins such as polyethylene terephthalate and polyurethane.

[0022] [Bacteria or Viruses to be Applied to] The antibacterial or antiviral agent of the present disclosure can inhibit the growth of a wide variety of bacteria or viruses.

[0023] The type of bacteria to which the antibacterial or antiviral agent of the present disclosure is applied is not particularly limited, and may be either gram-positive or gram-negative bacteria. Specifically, gram-positive bacteria to which the antibacterial or antiviral agent of the present disclosure is applied include Staphylococcus aureus, etc.; Bacillus bacteria; Listeria bacteria; Alicyclobacillus bacteria, etc. Gram-negative bacteria to which the antibacterial or antiviral agent of the present disclosure is applied include Escherichia bacteria, such as Escherichia coli; Klebsiella bacteria, such as Klebsiella pneumoniae; Pseudomonas bacteria, such as Pseudomonas aeruginosa; Salmonella bacteria; Vibrio bacteria; Acinetobacter bacteria, etc. Among these bacteria, preferred examples of bacteria to which the antibacterial or antiviral agent of the present disclosure is applied include Staphylococcus, Escherichia bacteria, and Klebsiella bacteria.

[0024] The type of virus to which the antibacterial or antiviral agent of the present disclosure is applied is not particularly limited, and may be either an enveloped virus or a non-enveloped virus. Specifically, enveloped viruses to which the antibacterial or antiviral agent of the present disclosure is applied include influenza virus, coronaviruses (HCoV-229E, HCoV-OC43, HCoV-NL63, HCoV-HKU1), novel coronavirus (SARS-CoV-2), herpes virus, respiratory syncytial virus, etc. Non-enveloped viruses to which the antibacterial or antiviral agent of the present disclosure is applied include feline calicivirus, norovirus, rotavirus, poliovirus, adenovirus, etc. Among these viruses, influenza virus, feline calicivirus, and norovirus are preferred examples of viruses to which the antibacterial or antiviral agent of the present disclosure is applied.

[0025] [Target of application, method of use, etc.] The antibacterial or antiviral agent of the present disclosure is used to impart an antibacterial or antiviral effect to a target for which antibacterial or antiviral effect is desired by treating the target. Targets for which antibacterial or antiviral effect is desired include not only spaces or objects where bacteria or viruses are present or attached, but also spaces or objects for which bacterial attachment or proliferation or viral attachment is desired to be inhibited even when bacteria or viruses are not present or attached.

[0026] By treating a space with the antibacterial or antiviral agent of the present disclosure, an antibacterial or antiviral effect can be imparted not only to the space but also to items present in the space. Examples of items present in the space that can be imparted with an antibacterial or antiviral effect include trash cans, sofas, chairs, desks, electrical appliances, sinks, toilets, bathtubs, washbasins, curtains, carpets, bedding, clothing, shoes, leather products, storage furniture, wallpaper, doors, floors, windows, and ceilings.

[0027] To treat a space with the antibacterial or antiviral agent of the present disclosure, the antibacterial or antiviral agent of the present disclosure may be vaporized or sprayed in the space. When the antibacterial or antiviral agent of the present disclosure is used for antibacterial or antiviral purposes in a space, the antibacterial or antiviral agent of the present disclosure may be mixed with a volatilizable solvent to provide an antibacterial or antiviral composition for use in a space.

[0028] The content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral composition for space may be set appropriately depending on the type, size, and the like of the space to which it is to be applied; for example, the amount of the compound is 0.1 to 99.9 wt %, preferably 1 to 99.9 wt %, and more preferably 1 to 80 wt %.

[0029] The solvent used in the antibacterial or antiviral composition for air space may be any solvent that can solubilize or disperse the antibacterial or antiviral agent of the present disclosure and that is volatilizable at room temperature, and examples thereof include water, paraffinic hydrocarbons (transparent liquid isoparaffin, transparent liquid normal paraffin), 3-methoxy-3-methyl-1-butanol, propylene glycol monomethyl ether, etc. These solvents may be used alone or in combination of two or more. In the antibacterial or antiviral composition for air space, the content of the solvent may be any solvent as long as it accounts for the remainder other than the antibacterial or antiviral agent of the present disclosure and any additives added as needed.

[0030] Furthermore, the antibacterial or antiviral composition for spatial use may contain other additives in addition to the antibacterial or antiviral agent of the present disclosure. Examples of other additives that can be incorporated into the antibacterial or antiviral composition for spatial use include surfactants, antioxidants, pH adjusters, fragrances, deodorizers, disinfectants, UV absorbers, insecticidal components, insect repellent components, repellent components, gelling agents, etc.

[0031] The form of the antibacterial or antiviral composition for space is not particularly limited, as long as it allows the antibacterial or antiviral agent of the present disclosure to be vaporized or sprayed; for example, if the composition is to be left to volatilize by standing, it may be in a liquid or gel form, or if the composition is to be sprayed, it may be in a liquid form.

[0032] To volatilize the antibacterial or antiviral composition for space in a space, the antibacterial or antiviral composition for space may be left stationary in the space in a volatilizable state in the same manner as conventional stationary air fresheners. To spray the antibacterial or antiviral composition for space in a space, a spray container, an aerosol container, an ultrasonic diffuser, an electric diffuser, or the like may be used.

[0033] The space to which the antibacterial or antiviral composition for space can be applied may be any space separated from the outdoors, and examples thereof include box spaces such as trash cans and shoe cabinets; indoor spaces such as living rooms, toilets, bathrooms, washrooms, entrances, and closets; interior spaces of automobiles, buses, trucks, and the like; and spaces within facilities such as restaurants, factories, offices, and conference rooms. A suitable example of a space into which the antibacterial or antiviral agent of the present disclosure is to be vaporized is the inside of a trash can or a space where a trash can is installed. Because trash cans are prone to bacterial growth and can also cause bad odors, the bad odor can be prevented or eliminated by vaporizing the antibacterial or antiviral agent of the present disclosure into the inside of a trash can or a space where a trash can is installed.

[0034] Antibacterial or antiviral use of articles By treating an article with the antibacterial or antiviral agent of the present disclosure, it is possible to impart an antibacterial or antiviral effect to the article.

[0035] To treat an article with the antibacterial or antiviral agent of the present disclosure, the antibacterial or antiviral agent of the present disclosure may be applied or sprayed onto the article. When the antibacterial or antiviral agent of the present disclosure is used for antibacterial or antiviral purposes on an article, the antibacterial or antiviral agent of the present disclosure may be mixed with a solvent to provide an antibacterial or antiviral composition for the article.

[0036] The content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral composition for use on articles may be set appropriately depending on the space to which it is to be applied, the type of article, and the like; for example, the amount of the compound is 0.1 to 99.9 wt %, preferably 1 to 99.9 wt %, and more preferably 1 to 80 wt %.

[0037] The solvent used in the antibacterial or antiviral composition for articles may be any solvent that can solubilize or disperse the antibacterial or antiviral agent of the present disclosure, and examples thereof include water, ethanol, propanol, etc. These solvents may be used alone or in combination of two or more. In the antibacterial or antiviral composition for articles, the content of the solvent may be any content that accounts for the remainder other than the antibacterial or antiviral agent of the present disclosure and any additives added as needed.

[0038] Furthermore, the antibacterial or antiviral composition for an article may contain other additives in addition to the antibacterial or antiviral agent of the present disclosure. Examples of other additives that can be incorporated into the volatile antibacterial or antiviral composition include surfactants, antioxidants, pH adjusters, fragrances, deodorizers, disinfectants, UV absorbers, insecticidal components, insect repellent components, and repellent components.

[0039] The antibacterial or antiviral composition for an article may be provided in the form of a wipe sheet, for example, by impregnating a fabric such as a nonwoven fabric, or in the form of a spray or aerosol, so that it can be easily applied or sprayed onto the article to which it is to be applied.

[0040] Examples of articles to which the antibacterial or antiviral compositions for articles can be applied include textile products such as fabric sofas, bedding, clothing, curtains, masks, diapers, wet towels, and carpets; hard surfaces such as toilets, bathtubs, washbasins, sinks, tiles, and glass; architectural structures such as wallpaper, doors, handrails, floors, windows, and ceilings; trash cans, chairs, desks, electrical appliances, storage furniture, shoe cabinets, shoes, and leather products.

[0041] A suitable example of an article to which the antibacterial or antiviral agent of the present disclosure can be applied is a trash can. Because trash cans are prone to bacterial growth and can cause bad odors, treating the trash can with the antibacterial or antiviral agent of the present disclosure can prevent or eliminate the bad odors.

[0042] Another suitable example of an article to which the antibacterial or antiviral agent of the present disclosure can be applied is a textile product.

[0043] Furthermore, still another suitable example of an article to which the antibacterial or antiviral agent of the present disclosure can be applied is a hard surface, particularly a hard surface made of plastic. A suitable embodiment of treating a hard surface with the antibacterial or antiviral agent of the present disclosure is to use 3-methyl-1-pentanol and / or 2,5-dimethylfuran as the antibacterial or antiviral agent of the present disclosure.

[0044] - Antibacterial or antiviral use on the body When applied to the skin, the antibacterial or antiviral agent of the present disclosure can impart antibacterial or antiviral effects to the skin and keep the skin in a hygienic state.

[0045] When the antibacterial or antiviral agent of the present disclosure is applied to the skin, it may be provided as an antibacterial or antiviral topical composition containing the antibacterial or antiviral agent of the present disclosure.

[0046] The content of the antibacterial or antiviral agent of the present disclosure in the antibacterial or antiviral composition for topical use may be set appropriately depending on the formulation form of the composition for topical use, etc., and examples of the amount of the compound include 0.1 to 50 wt %, preferably 0.1 to 30 wt %, and more preferably 0.1 to 10 wt %.

[0047] An antibacterial or antiviral topical composition can be formulated by blending an additive or a base with the antibacterial or antiviral agent of the present disclosure. The antibacterial or antiviral topical composition can be in any formulation, such as a topical skin drug, cosmetic, or skin cleanser, as long as it is applied to the skin. Specific formulations of the antibacterial or antiviral topical composition include topical skin drugs such as creams, lotions, gels, emulsions, liquids, poultices, patches, liniments, aerosols, aqueous ointments, packs, hand gels, and hand sanitizers; cosmetics such as aqueous ointments, creams, emulsions, lotions, packs, and gels; and skin cleansers such as body shampoos, hair shampoos, rinses, and wet wipes.

[0048] Use for the purpose of improving shelf life or durability The antibacterial or antiviral agent of the present disclosure can function as a preservative by being incorporated into products that require antibacterial or antiviral properties, and can also improve the shelf life or durability of the product.

[0049] The types of products that require antibacterial or antiviral properties are not particularly limited, but examples include foods, pharmaceuticals, cosmetics, textile products, resin products, and paper products.

[0050] The content of the antibacterial or antiviral agent of the present disclosure in the product may be set appropriately depending on the type of product and the like, and examples of the amount of the compound include 0.1 to 50 wt %, preferably 0.1 to 30 wt %, and more preferably 0.1 to 10 wt %.

[0051] If the product is a food, pharmaceutical, or cosmetic, the antibacterial or antiviral agent of the present disclosure may be blended as an additive. If the product is a textile, resin, or paper product, the antibacterial or antiviral agent of the present disclosure may be kneaded into the materials used in the production of these products.

[0052] The present disclosure will be explained in more detail below by showing examples, but the present disclosure is not limited to these examples.

[0053] Test Example 1: Evaluation of antibacterial activity against bacteria smeared on agar medium 1. Test materials and test method In this test, a volatile substance and a test strain were placed in a closed space without contact, and the antibacterial activity exerted by the volatilization of the test sample was evaluated. The specific test materials and test method are as follows.

[0054] (1) Test Bacterial Strains Staphylococcus aureus (NBRC12732) and Escherichia coli (NBRC3972) were prepared as test bacterial strains.

[0055] (2) Preparation of test bacterial solution A colony of the test bacterial strain cultured on SCD agar medium was scraped off with a 10 μl disposable loop, and added to 10 mL of sterile saline and thoroughly stirred to prepare a test bacterial suspension. The number of bacteria in the test bacterial suspension was then measured using the colony-forming unit (CFU) counting method (smear plate culture method), and the test bacterial suspension was diluted with sterile saline to a concentration of approximately 1.0 × 10 7 A test bacterial solution of cfu / mL was prepared.

[0056] (3) Preparation of test bacterial plates 0.1 mL of each test bacterial solution was smeared on an SCD plate medium (a petri dish with a diameter of 9.0 cm and a height of 2.0 cm was used) to prepare test bacterial plates. The test bacterial plates were prepared immediately before the antibacterial test described below.

[0057] (4) Assembly of test container The outer bottom of glass Petri dish B (diameter 2.6 cm, height 1.2 cm) was attached to the center of the inner bottom of glass Petri dish A (diameter 8.5 cm, height 3.0 cm) with double-sided tape to form a test container.

[0058] (5) Preparation of test samples The undiluted solutions (100%) of each volatile substance shown in Tables 1 and 2, and diluted solutions obtained by diluting them with isoparaffin to the concentrations shown in Tables 1 and 2, were used as test samples.

[0059] (6) Antibacterial Test: 1 ml of test sample was added to glass Petri dish B of the test container. Next, the test bacterial plate was placed in the test container so that the inner bottom of glass Petri dish A of the test container faced the inner bottom of the test bacterial plate (the side with the SCD plate medium smeared with the test bacterial solution). The test container and the test bacterial plate were then sealed with Parafilm to prevent any gaps at the interface between them. The test sample and the test bacterial strain were then left in a sealed space without contact and incubated at 37°C for 24 hours. A control was also incubated under the same conditions as above, except that no test sample was added to glass Petri dish B. After 24 hours, the extent of test bacterial growth on the test bacterial plate was visually confirmed, and the antibacterial activity was evaluated according to the following criteria. <Criteria for Antibacterial Activity> A: No colonies were formed on the test bacterial plate, indicating complete inhibition of bacterial growth. B: Colonies were observed on the test bacterial plate, but colony formation was clearly suppressed compared to the control, demonstrating bacterial growth inhibition. C: Colonies were observed all over the test bacteria plate, and the number of colonies formed was the same as in the control, and bacterial growth was not suppressed.

[0060] 2. Test Results The results are shown in Table 1. 3-methyl-1-pentanol, 1-hexen-3-ol, 4-methyl-2-pentanol, 2,5-dimethylfuran, 1-azacycloheptane, or ethyl pyruvate were able to exert excellent antibacterial activity against Staphylococcus aureus and Escherichia coli by volatilization (Examples 1 to 6).

[0061]

[0062] Test Example 2: Evaluation of antibacterial activity on fiber surfaces 1. Test materials and test method In this test, a fiber piece was left standing in an environment where volatile substances were evaporated, and then the fiber piece was left standing in contact with a test strain to evaluate the antibacterial activity of the fiber piece. The specific test materials and test method are as follows.

[0063] (1) Test Bacterial Strains Staphylococcus aureus (NBRC12732) and Klebsiella pneumoniae (NBRC13277) were prepared as test bacterial strains.

[0064] (2) Preparation of test bacterial solution One loopful of the test strain cultured on SCD agar medium was taken, suspended in 20 mL of NB liquid medium, and cultured with shaking at 37°C for 18 to 24 hours. 0.4 mL of the cultured bacterial solution was taken, suspended in 20 mL of NB liquid medium, and cultured with shaking at 37°C for 2 to 4 hours. The number of bacteria in the resulting culture was then counted by colony-forming unit (CFU) counting (smear plate culture method). The culture was diluted with 1 / 20 NB liquid medium to a concentration of 1.0 to 3.0 x 10 5 A test bacterial solution of cfu / mL was prepared.

[0065] (3) Preparation of test samples The undiluted solutions (100%) of each volatile substance shown in Table 2 and diluted solutions obtained by diluting them with isoparaffin to the concentrations shown in Table 2 were used as test samples.

[0066] (4) Preparation of Test Specimen-Treated and Untreated Fibers. 0.4 g of cut cotton fabric (2 cm × 2 cm square) or 0.2 g of polyethylene terephthalate (PET) fabric (2 cm × 2 cm square) was placed next to glass dish B (2.6 cm diameter, 1.2 cm height) on the inner bottom of glass dish A (8.5 cm diameter, 3.0 cm height). 0.5 mL of the test specimen was added to the inside of glass dish B, and glass dish A was covered with a lid, ensuring that the test specimen and cotton fabric were not in contact with each other in an enclosed space. This was left at room temperature for 30 minutes to obtain test specimen-treated fibers. The test specimen-treated fibers were prepared immediately before the antibacterial test described below. Additionally, 0.4 g of untreated cotton fabric (2 cm × 2 cm square) or 0.2 g of PET fabric (2 cm × 2 cm square) was prepared as untreated treated fibers.

[0067] (5) Antibacterial Test: Test specimen-treated or untreated fiber was placed in a vial, and 200 μL of test bacteria solution was inoculated evenly over the entire surface of the test specimen-treated or untreated fiber. The vial was then capped and allowed to stand at 37°C for 24 hours. Next, 20 mL of SCDLP liquid medium was added to the vial and thoroughly stirred to disperse the bacteria in the SCDLP liquid medium, obtaining a bacterial dispersion. The number of bacteria in the bacterial dispersion was then measured using the colony-forming unit (CFU) counting method (smear plate culture method), and the antibacterial activity value was calculated according to the following formula:

[0068] The antibacterial activity was evaluated based on the antibacterial activity value according to the following criteria: <Criteria for evaluation of antibacterial activity> A: Antibacterial activity value of 3.0 or more (high antibacterial activity) B: Antibacterial activity value of 2.0 or more but less than 3.0 (antibacterial activity) C: Antibacterial activity value of less than 2.0 (no antibacterial activity)

[0069] 2. Test Results The results are shown in Table 2. The fibers placed in a space where 3-methyl-1-pentanol, 1-hexen-3-ol, 2,5-dimethylfuran, or 1-azacycloheptane had been evaporated exhibited excellent antibacterial activity against Staphylococcus aureus or Klebsiella pneumoniae (Examples 1, 2, 4, and 5). However, the fibers placed in a space where hexanol or octanol had been evaporated did not have antibacterial activity against Staphylococcus aureus or Klebsiella pneumoniae (Comparative Examples 1 and 2).

[0070]

[0071] Test Example 3: Evaluation of antibacterial activity on hard surfaces 1. Test materials and test method In this test, a polyurethane plate was placed in an environment where volatile substances were evaporated, and then the plate was placed in contact with a test strain to evaluate the antibacterial activity of the plate. The specific test materials and test method are as follows.

[0072] (1) Test Bacterial Strains Staphylococcus aureus (NBRC12732) and Escherichia coli (NBRC3972) were prepared as test bacterial strains.

[0073] (2) Preparation of test bacterial solution: Take one loopful of test strain cultured on SCD agar medium at 34-36°C for 16-24 hours, dilute the culture with 1 / 500 NB liquid medium, and prepare 2.5-10 x 10 5 A test bacterial solution of cfu / mL was prepared.

[0074] (3) Preparation of Test Samples The stock solutions of the volatile substances shown in Table 3 were diluted with isoparaffin to the concentrations shown in Table 3 to prepare test samples.

[0075] (4) Preparation of Test Sample-Treated Plates and Untreated Plates: A cut polyurethane plate (4.8 cm × 4.8 cm square) and glass dish B (2.6 cm diameter, 1.2 cm height) were placed side by side on the inner bottom of glass dish A (8.5 cm diameter, 3.0 cm height). 0.5 mL of the test sample was added to glass dish B, and glass dish A was covered, creating a sealed space where the test sample and cotton cloth were not in contact with each other. This was left at room temperature for 30 minutes to obtain a test sample-treated plate. The test sample-treated plate was prepared immediately before the antibacterial test described below. A polyurethane plate (4.8 cm × 4.8 cm square) that had not undergone the above treatment was also prepared as an untreated plate.

[0076] (5) Antibacterial Test: 400 μL of test bacterial solution was evenly inoculated over the entire surface of a test specimen-treated or untreated plate, covered with parafilm (4 cm × 4 cm square), and allowed to stand at 35°C and a relative humidity of 90% or higher for 24 hours. Next, while still covered with parafilm, the test specimen-treated or untreated plate was transferred to a vinyl bag, and 10 mL of SCDLP liquid medium was added. The outside of the vinyl bag was thoroughly kneaded by hand to disperse the bacteria in the SCDLP liquid medium, yielding a bacterial dispersion. The number of bacteria in the bacterial dispersion was then measured using the colony-forming unit (CFU) counting method (smear plate culture method), and the antibacterial activity value was calculated according to the following formula:

[0077] The antibacterial activity was evaluated based on the antibacterial activity value according to the following criteria: <Criteria for evaluation of antibacterial activity> A: Antibacterial activity value of 3.0 or more (high antibacterial activity) B: Antibacterial activity value of 2.0 or more but less than 3.0 (antibacterial activity) C: Antibacterial activity value of less than 2.0 (no antibacterial activity)

[0078] 2. Test Results The results are shown in Table 3. The polyurethane plates placed in the space where 2,5-dimethylfuran or 1-azacycloheptane was evaporated exhibited excellent antibacterial activity against Staphylococcus aureus and Escherichia coli (Examples 4 and 5). However, the polyurethane plates placed in the space where octanol was evaporated did not have antibacterial activity against Staphylococcus aureus or Escherichia coli (Comparative Example 2).

[0079]

[0080] Test Example 4: Evaluation of antiviral activity on fiber surfaces 1. Test materials and test method In this test, a fiber piece was left standing in an environment where volatile substances had been evaporated, and then the fiber piece was left standing in contact with a test virus to evaluate the antiviral activity of the fiber piece. The specific test materials and test method are as follows.

[0081] (1) Test Viruses Influenza A virus (H1N1); strain: ATCC VR-1469, host cells: MDCK (NBL-2) cells) and feline calicivirus (strain: ATCC VR-782, host cells: CRFK cells) were prepared as test viruses.

[0082] (2) Preparation of test virus solution The prepared host cells were inoculated with the virus solution diluted with EMEM(-) and cultured overnight at 37°C in the presence of 5% CO2. After centrifugation, the supernatant was collected to prepare 1.0 x 10 7 ~1.0×10 8 A virus suspension of pfu / mL was prepared, and then the resulting virus suspension was diluted 10-fold with sterile purified water to prepare a test virus solution.

[0083] (3) Preparation of test samples Undiluted solutions (100%) of the volatile substances shown in Table 4 and diluted solutions obtained by diluting them with isoparaffin to the concentrations shown in Table 4 were used as test samples.

[0084] (4) Preparation of Test Sample-Treated and Untreated Fibers. A 0.4 g piece of cut cotton cloth (2 cm × 2 cm square) and a glass dish B (2.6 cm diameter, 1.2 cm height) were placed side by side on the inner bottom of a glass Petri dish A (8.5 cm diameter, 3.0 cm height). 0.5 mL of the test sample was added to the inside of glass Petri dish B, and the glass dish A was covered to prevent contact between the test sample and the cotton cloth in an enclosed space. In this state, the test sample was left to stand at room temperature for 30 minutes when a 10% diluted solution was used, and for 3 hours when a 30% diluted solution or the undiluted solution (100%) was used, to obtain test sample-treated fibers. The test sample-treated fibers were prepared immediately before the antiviral test described below. Additionally, 0.4 g of untreated cotton cloth (2 cm × 2 cm square) was prepared as an untreated fiber.

[0085] (5) Antiviral Test: Test specimen-treated or untreated fibers were placed in a vial, and 200 μL of the test virus solution was inoculated evenly over the entire surface of the test specimen-treated or untreated fibers. The vial was then capped and allowed to stand at 25°C for 18 hours. Next, 20 mL of SCDLP liquid medium was added to the vial, and the mixture was thoroughly stirred to disperse the virus in the SCDLP liquid medium, yielding a virus dispersion. Then, 0.1 mL of the virus dispersion was added to 0.9 mL of EMEM(-), and the number of plaques was counted by the plaque assay. The antiviral activity value was calculated according to the following formula:

[0086] The antiviral effect was evaluated based on the antiviral activity value according to the following criteria: <Criteria for evaluating antiviral effect> A: Antiviral activity value of 3.0 or more (high antiviral effect) B: Antiviral activity value of 2.0 or more but less than 3.0 (antiviral effect) C: Antiviral activity value of less than 2.0 (no antiviral effect)

[0087] 2. Test Results The results are shown in Table 4. The fiber pieces placed in a space where 3-methyl-1-pentanol, 1-hexen-3-ol, 4-methyl-2-pentanol, 2,5-dimethylfuran, 1-azacycloheptane, or ethyl pyruvate had been evaporated exhibited excellent antiviral activity against influenza virus or feline calicivirus (Examples 1 to 6). However, the fiber pieces placed in a space where hexanol or octanol had been evaporated did not have antiviral activity against influenza virus or feline calicivirus (Comparative Examples 1 and 2).

[0088]

[0089] Test Example 5: Evaluation of antiviral activity on hard surfaces 1. Test materials and test method In this test, a polyurethane plate was placed in an environment where volatile substances had evaporated, and then the plate was placed in contact with a test virus to evaluate the antiviral activity of the plate. The test materials and test method were the same as those in Test Example 4, except that a polyurethane plate (4.8 cm x 4.8 cm square) was used instead of the fiber piece and the amount of test virus solution placed in the vial was changed to 400 μL.

[0090] 2. Test Results The results are shown in Table 5. The polyurethane plates placed in a space where 2,5-dimethylfuran, 1-azacycloheptane, or ethyl pyruvate had been evaporated exhibited excellent antiviral activity against influenza virus or feline calicivirus (Examples 4 to 6). However, the polyurethane plates placed in a space where hexanol or octanol had been evaporated did not have antiviral activity against influenza virus or feline calicivirus (Comparative Examples 1 and 2).

[0091]

Claims

1. An antibacterial or antiviral agent comprising at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane.

2. An antibacterial or antiviral method for treating a target for which antibacterial or antiviral properties are desired, using at least one compound selected from the group consisting of 3-methyl-1-pentanol, 2,5-dimethylfuran, 1-hexen-3-ol, 4-methyl-2-pentanol, ethyl pyruvate, and 1-azacycloheptane.

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