Agent for antiviral and / or antibacterial use

Abstract

The present invention addresses the problem of finding a novel active active ingredient having both antiviral activity and antibacterial activity, and providing a novel antiviral / antibacterial agent excellent in terms of safety, viral inhibition, and antibacterial effect. More specifically, provided is an agent for antiviral and / or antibacterial use, said agent containing galactaric acid and / or a salt thereof as an active ingredient.

Description

Agents for use as antiviral and / or antibacterial agents

[0001] The present invention relates to an agent for use as an antiviral and / or antibacterial agent, a product having antiviral and / or antibacterial properties, a method for inhibiting viruses and / or infecting nonhumans, a method for producing articles that have been treated with antiviral and / or antibacterial agents, and an antiviral and pest control composition containing the antiviral and / or antibacterial agent and a known pest control agent.

[0002] Viral infections such as influenza and norovirus have repeatedly spread, and because these viruses cause severe symptoms such as high fever, severe vomiting, and diarrhea, consumers are highly conscious of infection prevention. Therefore, there is a growing demand for not only anti-pest control properties (antibacterial, antifungal, anti-algal, etc.) but also antiviral properties in everyday items. However, while conventionally known disinfectants such as ethanol preparations have been reported to be effective against the enveloped virus, the novel coronavirus, within the ethanol concentration range specified by the pharmacopoeia, the antiviral properties are lost once the ethanol evaporates from the applied surface, and the effect does not last, requiring repeated spraying or coating of the treated object. Furthermore, there is a concern that the treated object may deteriorate, making application difficult in some cases. Therefore, although it has been reported that combining quaternary ammonium salts with ethanol can enhance antiviral activity (e.g., Patent Documents 1 and 2), there have been no reports of a new antiviral agent that possesses excellent antiviral properties that can efficiently inactivate viruses in a short time and maintain antiviral properties in a solid state. Furthermore, no drug possessing both antiviral and antibacterial activity has yet been discovered.

[0003] Japanese Patent Publication No. 2022-032131 Japanese Patent Publication No. 2022-029409

[0004] The present invention aims to provide a new antiviral and antibacterial agent that possesses both antiviral and antibacterial activity, and is superior in terms of safety, virus suppression, and antibacterial effect.

[0005] The inventors conducted extensive research to solve the above problems and discovered that galactaric acid, a sugar acid derived from galactose, exhibits not only virus-inhibiting effects but also antibacterial effects, thus resolving the aforementioned issues.

[0006] The present invention is specifically summarized as follows: 1. An agent for antiviral and / or antibacterial use comprising galactaric acid and / or its salt as an active ingredient. 2. A product having antiviral and / or antibacterial properties containing the agent for antiviral and / or antibacterial use described in 1. 3. A method for inhibiting viruses and / or infecting nonhumans using the agent for antiviral and / or antibacterial use described in 1. 4. A method for producing an antiviral and / or antibacterial processed article, comprising incorporating the agent for antiviral and / or antibacterial use described in 1. into the article or coating the surface of the article with it. 5. An antiviral and pest control composition containing the agent for antiviral and / or antibacterial use described in 1. and a pest control agent. 6. An antiviral and pest control product containing the antiviral and pest control composition described in 5. 7.5. A method for producing an article that has been treated with antiviral and pest control, comprising incorporating the antiviral and pest control composition described herein into the article or coating it on the surface of the article.

[0007] The antiviral and / or antibacterial agent of the present invention is extremely useful because it contains galactaric acid as an active ingredient, which is highly safe and, in particular, does not raise concerns about skin irritation, and exhibits excellent virus-suppressing and / or antibacterial effects. In particular, even when the antiviral and / or antibacterial agent of the present invention is used in a paint coating, it exhibits excellent virus-suppressing and / or antibacterial effects, so when applied to various industrial products and materials, it can impart safe virus-suppressing and / or antibacterial effects. Furthermore, by using the antiviral and / or antibacterial agent of the present invention in combination with known pest control agents, a synergistic pest control effect exceeding the additive effect is exhibited, thus reducing the amount of known pest control agents used, which is extremely useful.

[0008] The following describes in detail the agent for use in antiviral and / or antibacterial purposes of the present invention, products having antiviral and / or antibacterial properties, methods for suppressing viruses and / or antibacterial purposes, and methods for producing articles that have been processed with antiviral and / or antibacterial properties. Furthermore, it describes in detail an antiviral and pest control composition containing the agent for use in antiviral and / or antibacterial purposes of the present invention and a known pest control agent. <Galactaric acid and / or its salts> The agent for use in antiviral and / or antibacterial purposes of the present invention contains galactaric acid and / or its salts as active ingredients. Galactaric acid has a formyl group (-CHO) at the 1 position of galactose and a hydroxymethyl group (-CH) at the end of the main chain. ２ Galactaric acid is a dicarboxylic acid having the following chemical structure, in which both OH) groups are carboxyl groups, and is a compound obtained by nitrate oxidation of galactose. Although galactaric acid exists in L and D forms, the L and D forms, mixtures thereof, and any compound having the following chemical structure are included as active ingredients in the present invention. Galactaric acid is an ingredient permitted for use in cosmetics as a chelating agent. In addition to its chelating effect, it also has the effect of prolonging the life of skin cells, and therefore many cosmetics containing galactaric acid are sold. In other words, galactaric acid is a highly safe substance with no concerns regarding skin irritation or damage. The agent for antiviral and / or antibacterial use of the present invention uses galactaric acid as an active ingredient, which is highly safe, especially with no concerns regarding skin irritation. Therefore, products containing the agent for antiviral and / or antibacterial use of the present invention can also be highly safe products. Examples of galactaric acid salts include sodium galactarate, disodium galactarate, potassium sodium galactarate, dipotassium galactarate, diammonium galactarate, and zinc galactarate. The active ingredient of the agent for antiviral and / or antibacterial use of the present invention can be galactaric acid and / or its salts used in combination, one or more of them.

[0009] <Target Viruses> The target viruses for the antiviral and / or antibacterial agents of the present invention are not particularly limited, but include, for example, influenza viruses (e.g., type A, type B, etc.), rubella viruses, Ebola viruses, coronaviruses, measles viruses, varicella-zoster viruses, herpes viruses, mumps viruses, arboviruses, RSV viruses, SARS viruses, hepatitis viruses (e.g., hepatitis A virus, hepatitis B virus, hepatitis C virus, hepatitis D virus, hepatitis E virus, etc.), yellow fever viruses, HIV, rabies viruses, hantaviruses, dengue viruses, nipah viruses, lyssaviruses, and other enveloped viruses (viruses having an envelope); and non-enveloped viruses (viruses without an envelope) such as adenoviruses, noroviruses, rotaviruses, feline caliciviruses, human papillomaviruses, polioviruses, enteroviruses, coxsackieviruses, human parvoviruses, encephalomyocarditis viruses, polioviruses, rhinoviruses, and others. Viruses possess genes, which are contained within an outer shell protein called a capsid. Therefore, viruses are broadly classified according to whether their genes are DNA or RNA, and further classified into those with and without an envelope covering the capsid. Specifically, herpes viruses are examples of viruses with DNA genes and an envelope, adenoviruses are examples of viruses with DNA genes and no envelope, influenza viruses are examples of viruses with RNA genes and an envelope, and noroviruses, feline caliciviruses, and polioviruses are examples of viruses with RNA genes and no envelope. The antiviral and / or antibacterial agent of the present invention can be suitably used to suppress enveloped viruses and non-enveloped viruses. In terms of effectiveness, application to the suppression of enveloped viruses is more preferable, and application to the suppression of influenza viruses is even more preferable.

[0010] <Target Fungi> The target fungi of the antiviral and / or antibacterial agents of the present invention refer to bacteria, and do not include fungi such as molds, yeasts, and wood-rotting fungi, or algae. Examples of bacteria include Gram-negative bacilli such as Escherichia coli, Pseudomonas aeruginosa, and Serratia marcescens; Gram-positive bacilli such as Bacillus subtilis and Clostridium species; Gram-negative cocci such as Branhamella; and Gram-positive cocci such as Staphylococcus aureus.

[0011] <Formulation> The antiviral and / or antibacterial agent of the present invention can be made into various formulations by dissolving, dispersing, etc., in various carriers such as liquid carriers and solid carriers, in addition to the active ingredient galactaric acid and / or its salt, depending on the purpose and use, within a range that does not affect the virus-inhibiting effect, antibacterial effect and stability. Examples include liquid formulations such as wettable powders, suspensions, dispersants, emulsions, and oils; solid formulations such as powders, granules, microcapsules, microspheres, flowables, and foaming agents; semi-solid formulations such as pastes and creams; sprays and aerosols; and paints, which can be appropriately selected according to the purpose of use and application conditions. These formulations can be manufactured by conventional methods. The content of the active ingredient galactaric acid and / or its salt in the antiviral and / or antibacterial agent of the present invention can be adjusted according to the desired virus-inhibiting effect and antibacterial effect, and is not particularly limited, but can be, for example, 0.0001 to 100% by weight, preferably 0.001 to 50% by weight.

[0012] The liquid carriers that can be used in the present invention include water; lower alcohols such as methanol, ethanol, n-propanol, isopropanol, and n-butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, ethylene glycol monomethyl ether (methyl carbitol), ethylene glycol monoethyl ether (ethyl carbitol), ethylene glycol monobutyl ether (butyl carbitol), diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and triethylene glycol butyl ether; acetone, methyl ethyl Examples of liquid carriers include ketones such as ketones, methyl isobutyl ketone, and propylene carbonate; ethers such as dioxane, tetrahydrofuran, and ethyl ether; esters such as ethyl acetate, butyl acetate, isobutyl acetate, 3-methyl-3-methoxybutyl acetate, γ-butyrolactone, dimethyl adipate, dimethyl glutarate, and dimethyl succinate; aromatic solvents such as benzene, toluene, xylene, methylnaphthalene, dimethylnaphthalene, isopropylnaphthalene, diisopropylnaphthalene, ethyl biphenyl, diethyl biphenyl, and solvent naphtha; halogenated hydrocarbon solvents such as carbon tetrachloride, chloroform, and methylene chloride; and polar organic solvents such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide, acetonitrile, and N-methylpyrrolidone. These liquid carriers may be used individually or in combination of two or more. Among these liquid carriers, water, ketones such as propylene carbonate, lower alcohols, and polyhydric alcohols are preferably used.

[0013] Examples of solid carriers that can be used in the present invention include diatomaceous earth, mica, clay, kaolin, talc, silica, bentonite, talc powder, soapstone powder, and other talc-based materials, as well as mineral powders such as fine clay and calcium carbonate; sulfur powder; urea powder; plant-based powders such as wood flour and starch; and various carriers commonly used as agents for antiviral and / or antibacterial purposes. These solid carriers are also often used as fillers. These solid carriers can be used individually or in combination of two or more. The aerosol agent can be manufactured by diluting the active ingredient, galactaric acid and / or its salt, with a suitable solvent as needed, and filling it into a container together with a propellant. Examples of solvents include the liquid carriers exemplified above. Examples of propellants include chlorofluorocarbons (CFCs) and liquefied natural gas.

[0014] The antiviral and / or antibacterial agent of the present invention may contain various additives as needed, depending on the type of formulation, such as stabilizers such as antioxidants and ultraviolet absorbers; binders; resins having film-forming ability; emulsifiers, dispersants, spreading agents, wetting agents, penetrating agents; thickeners; flow aids; anticaking agents; flocculants; ultraviolet scattering agents; water removal agents; colorants, etc.

[0015] Examples of antioxidants include phenolic antioxidants such as 4,4'-thiobis-6-t-butyl-3-methylphenol, butylated hydroxyanisole (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), p-octylphenol, mono(or di or tri)-(α-methylbenzyl)phenol, 2,6-di-t-butyl-p-cresol (BHT), and pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)]propionate; amine antioxidants such as N,N'-di-2-naphthyl-p-phenylenediamine; hydroquinoline antioxidants such as 2,5-di(t-amyl)hydroquinoline; sulfur-based antioxidants such as dilaurylthiodipropionate; and phosphorus-based antioxidants such as triphenyl phosphite. Examples of UV absorbers include benzotriazole compounds such as 2-(2'-hydroxy-5'-methylphenyl)benzotriazole and 2-(2'-hydroxy-4'-n-octoxyphenyl)benzotriazole; benzophenone compounds such as 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-n-octoxybenzophenone; salicylic acid compounds such as phenyl salicylate and p-t-butylphenyl salicylate; 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, bisanilide 2-ethoxy-2'-ethyl oxalate, and dimethyl-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate. Examples of binders include sodium carboxymethylcellulose salt, methylcellulose, ethylcellulose, hydroxymethylcellulose, dextrin, pregelatinized starch, polyvinyl alcohol, polyvinylpyrrolidone, sodium ligninsulfonate, and potassium ligninsulfonate.Examples of resins having film-forming ability include thermoplastic resins such as polyethylene, polyolefins such as polypropylene, polyvinyl acetate, polyvinyl alcohol, acrylic resins, polyvinyl chloride, styrene resins, fluororesins, chlorinated polyolefins, alkyd resins, polyamides, and polyesters; and thermosetting resins such as phenolic resins, urea resins, melamine resins, furan resins, unsaturated polyester resins, and epoxy resins. These resins include all forms, such as solvent-based and emulsion-based types.

[0016] Conventional surfactants such as anionic surfactants and nonionic surfactants can be used as emulsifiers, dispersants, spreading agents, wetting agents, and penetrating agents. Examples of anionic surfactants include metal soaps, sulfate esters such as alkyl sodium sulfate, alkylbenzene sulfonates such as alkylbenzene sulfonate, alkylnaphthalene sulfonates such as alkylnaphthalene sulfonate (e.g., manufactured by Takemoto Oil Co., Ltd., trade name New Calgen BX-C), dialkyl 2-sulfosuccinate salts such as dialkyl sodium 2-sulfosuccinate (e.g., manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name Neocol SW-C), polycarboxylic acid type surfactants (e.g., manufactured by Sanyo Chemical Industries, Ltd., trade name Toxanon GR-30), α-olefin sulfonates, polyoxyethylene distyrenated phenyl ether sulfate ammonium salt (e.g., manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name Dixzol 60A), sodium ligninsulfonate, and potassium ligninsulfonate. Examples of nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers (e.g., Daiichi Kogyo Seiyaku Co., Ltd., trade name Neugen (EA-142)), polyoxyethylene aryl ethers, fatty acid polyhydric alcohol esters, fatty acid polyhydric alcohol polyoxyethylene, sucrose fatty acid esters, and block copolymers of ethylene oxide and propylene oxide (e.g., Sanyo Chemical Industries, Ltd., trade name Newpol PE-64). Examples of thickeners include polyvinyl alcohol, polyacrylic acid and its salts, and examples of flow aids include PAP aids (e.g., isopropyl phosphoric acid), waxes, polyethylene, fatty acid metal salts, paraffin, organic lubricants such as silicone oil, and inorganic lubricants such as talc. Examples of anticaking agents include white carbon, diatomaceous earth, magnesium stearate, aluminum oxide, and titanium dioxide. Examples of flocculants include liquid paraffin, ethylene glycol, diethylene glycol, triethylene glycol, and isobutylene polymer (e.g., Idemitsu Kosan Co., Ltd., trade name IP Solvent-2835). Examples of ultraviolet scattering agents include titanium dioxide.Examples of moisture-removing agents include desiccants such as anhydrous gypsum and silica gel powder. Coloring agents include, for example, organic or inorganic pigments and dyes.

[0017] The antiviral and / or antibacterial agent of the present invention can be widely used in various fields requiring viral suppression and / or antibacterial effects. For example, the antiviral and / or antibacterial agent of the present invention can be used in various fields such as industry, livestock farming, cleaning, medical care, nursing care, food, and cosmetics to not only suppress viruses but also exhibit antibacterial effects. In particular, the antiviral and / or antibacterial agent of the present invention is preferably used as an antiviral and / or antibacterial agent in industrial settings, livestock farms such as poultry farms, and nursing care settings. More specific uses of the antiviral and / or antibacterial agent of the present invention include application to non-human objects (e.g., articles), specifically, by compounding it into articles, coating it on the surface of articles, and by spraying, misting, applying, or wiping it onto target locations or areas in livestock farming, medical care, nursing care, etc. This allows for simultaneous antiviral and antibacterial processing / treatment of articles and target locations or areas. In other words, it exerts a viral inhibitory effect and / or antibacterial effect against viruses and fungi already attached to articles or target locations, and also exerts a viral inhibitory effect and / or antibacterial effect against viruses and fungi that will be attached to articles or target locations in the future. Furthermore, it can exert a viral inhibitory effect and / or antibacterial effect against viruses and fungi already attached to, or that will be attached to, other articles, locations, or places that will come into contact with the said article or target location. Conventional known antiviral and / or antibacterial agents often contain active ingredients that raise safety concerns, and articles containing these agents have had problems such as skin irritation from contact. However, the antiviral and / or antibacterial agent of the present invention uses highly safe galactaric acid as its active ingredient, so articles treated with the antiviral and / or antibacterial agent of the present invention can also be made highly safe. In addition, the antiviral and / or antibacterial agent of the present invention is highly safe for people who perform treatments such as spraying, making it extremely useful.

[0018] Articles in this invention include industrial products and their raw materials used in various fields, as well as those used in various fields such as livestock farming, medical care, nursing care, food, and cosmetics. Specific examples include paints, adhesives, synthetic rubber latex, inks, polyvinyl alcohol films, vinyl chloride films, resin products, gypsum boards, roofing materials, wall materials, flooring materials, joinery, coated paper, wallpaper, exterior floor coverings, office automation equipment, home appliances, air conditioning equipment, vacuum cleaners, desks, chairs, sofas, benches, windows, straps, handles, seats, automatic ticket gates, automatic ticket vending machines, vending machines, doors, fences, handrails, tableware, cooking utensils, packaging films, packaging bags, bottles, containers, packaging packs, sinks, toilets, stationery, books, shelves, toothbrushes, mirrors, filters, masks, etc. Examples of articles in this invention include trousers, jackets, trousers, skirts, dress shirts, knit shirts, blouses, sweaters, cardigans, nightwear, underwear, diapers, supporters, socks, tights, stockings, hats, scarves, mufflers, neck wraps, stoles, gloves, clothing linings, clothing interlinings, clothing padding, work clothes, uniforms, school uniforms, and other clothing items, as well as curtains, screen doors, bedding fabrics, bedding cotton, bedding covers, pillowcases, sheets, mats, carpets, towels, handkerchiefs, wall coverings, bandages, plasters, gauze, cosmetics, and composite materials thereof. Industrial products are preferred as articles in this invention.

[0019] "Incorporating into an article" is not particularly limited as long as it involves the active ingredient of galactaric acid and / or its salt being contained in the article (preferably, in a manner in which the active ingredient of galactaric acid and / or its salt is present on the surface of the article), and can be appropriately selected depending on the type of article. Examples of incorporation include mixing into an article, kneading into an article during the manufacturing process, or impregnating an article (for example, an article made of a fiber aggregate).

[0020] "Coating the surface of an article" is not particularly limited as long as the active ingredient galactaric acid and / or its salt is present on the surface of the article, and can be appropriately selected depending on the type of article. Examples of coating methods include applying to the surface of the article, spraying onto the surface of the article, and immersing the surface of the article. The coating methods include both methods in which the active ingredient galactaric acid and / or its salt is fixed to the surface of the article and methods in which it is not fixed. In addition to "coating the surface of an article," the antiviral and / or antibacterial agent of the present invention can also be suitably used in diluted or undiluted form when spraying, misting, applying, wiping, etc., on places or areas where antiviral and / or antibacterial treatment is intended in livestock farming, medical care, nursing care, etc. This is useful because it allows for simultaneous antiviral and / or antibacterial treatment of the target place or area.

[0021] The amount of the antiviral and / or antibacterial agent of the present invention can be appropriately selected depending on the manner of use, the type of article to which it is applied, the period for which the virus-suppressing effect or antibacterial effect is expected, etc. For example, when incorporated into industrial products, there are no particular restrictions, but it is possible to incorporate 10 mg or more of the active ingredient galactaric acid and / or its salt per 1 kg of industrial product, and it is preferable to incorporate it in a way that the maximum amount is 300 g.

[0022] The antiviral and / or antibacterial agent of the present invention, when used in combination with known pest control agents to form an antiviral and pest control composition, exhibits a synergistic pest control effect that exceeds the additive effect, thereby reducing the amount of known pest control agents used. The pest control agents in the present invention include known antifungal and antiseptic agents, antibacterial agents, anti-algal agents, insecticides, and insect repellents. As an antiseptic and antifungal agent, which is one of the pest control agents in the present invention, isothiazoline-based: 2-methyl-4-isothiazolin-3-one (H-MIT), 5-chloro-2-methyl-4-isothiazolin-3-one (Cl-MIT), 1,2-benzothiazolin-3-one (BIT), 2-butyl-1,2-benzoisothiazol-3-one (B-BIT), 2-n-octyl-4-isothiazolin-3-one (OIT), 4,5-dichloro-2-n-octylisothiazol-3-one (DCOIT), etc., organobromine-based: 2-bromo-2-nitro-1,3-propanediol (BNPD), 2,2-dibromo-2-nitro-1-ethanol (DBNE), bis(1,4-bromoacetoxy)-2-butene (BBAB), 1, 2-Bis(bromoacetoxy)ethane (BBAE), etc., Benzimidazole derivatives: Carbendazim (1H-benzimidazole-2-ylcarbamate methyl, MBC), Thiabendazole (2-(1,3-thiazole-4-yl)-1H-benzimidazole, TBZ), Benomyl, Thiaphanate-methyl, etc., Azole derivatives: Imazalil, Tebuconazole, Hexaconazole, Propiconazole, Fluconazole, Itraconazole, Policonazole, Posaconazole, Isubconazole, etc., Iodine derivatives: N-butylcarbamate 3-iodo-2-propynyl (IPBC), Diiodomethyl-p-tolylsulfone (DMTS), Iodoacetamide (IAA), etc., Cationic derivatives: Benzalkonium chloride, Dimer 38 (N,N'-Hexamethylenebis(4-carbamoyl-1-decylpyridinium bromide), benzethonium chloride, cetylpyridinium chloride, didecylmethylammonium chloride, alkyldimethylbenzylammonium chloride, lauryltrimethylammonium chloride, myristoltrimethylammonium chloride, stearyltrimethylammonium chloride, dimethyldioctylammonium chloride, trimethylbenzylammonium chloride, trimethylammonium chloride, etc., Biguanide derivatives: poly(hexamethylenebiguanidine) hydrochloride (PH Pyrithione-based: Zinc pyrithione (ZPT), sodium pyrithione (NaPT), copper pyrithione (CuPT), iron pyrithione (FePT), magnesium pyrithione (MgPT), calcium pyrithione (CaPT), etc. Thiocyanate-based: (2-(thiocyanate methylthio)-1,3-benzothiazole) (TCMTB), methylene bisthiocyanate (MBTC), etc. Cyanide-based: 2,2-dibromo-3-nitrilopropionamide (DBNPA), chlorothalonyl, etc. Paraben-based: Methylparaben, ethylparaben Lavenders, propylparaben, butylparaben, isopropylparaben, isobutylparaben, hexylparaben (NHPB), benzylparaben, phenylparaben, etc. Glycol-based: phenoxyethanol, ethylhexylglycerin, caprylyl glycol, hexylene glycol, 1,2-hexanediol, 1,2-octanediol, butylene glycol, pentylene glycol, isoprene glycol, etc. Phenolic-based: chlorphenesin, o-cymen-5-ol, triclosan, hinokitiol, thymol, bio Zole (isopropylmethylphenol), 4-chloro-3-methylphenol, chlorooxylenol (PCMX), orthophenylphenol (OPP), paraphenylphenol (PPP), etc., Dimethylphenyl sulfamide series: diclofluanide, tolfluanide, dimethylphenyl sulfamide, etc., Organic acid series: benzoic acid, sorbic acid, propionic acid, acetic acid, lactic acid, citric acid, maleic acid, salicylic acid, galsolic acid, dehydroacetic acid, p-aminobenzoic acid, etc., Higher alcohol series: 1-decanol, 1-undecanol, 1,Examples include 2-dodecanediol, 2-dodecanol, and aldehydes such as glutaraldehyde and formaldehyde.

[0023] The antimicrobial agents used as pest control agents in this invention include: Old quinolone types: oxolinic acid, nalidixic acid, pipemidic acid, pyromidic acid, etc.; New quinolone types: norfloxacin, tosufloxacin, difloxacin, ofloxacin, marbofloxacin, levofloxacin, etc.; Sulfonamides: sulfadiazine, sulfadimethoxine, sulfanilamide, sulfamethoxazole, diaphenylsulfone, etc.; Tetracycline types Examples include: tetracyclines, daunorubicin hydrochloride, minocycline hydrochloride, chlortetracycline, etc.; lincomycin derivatives: lincomycin, clindamycin, etc.; chloramphenicol derivatives: chloramphenicol, etc.; penicillins: benzylpenicillin, ampicillin, methicillin, etc.; cephalosporins: cefazolin, cephalexin, cefotiam, etc.; aminoglycosides: kanamycin, streptomycin, gentamicin, etc.

[0024] Examples of algal repellents used as pest control agents in the present invention include triazine-based agents such as sibutrin, terbutrin, ametrin, simetrin, promethrin, zimagine, and 2-methylthio-4-cyclopropylamino-6-t-butylamino-1,3,5-triazine (MBACT), and hexahydrotriazine-based agents such as 5-tris(2-hydroxyethyl)-1,3,5-triazine (HTHE), 1,3,5-triacetylhexahydro-1,3,5-triazine, and 1,3,5-tributyrylhexahydro-1,3,5-triazine.

[0025] Examples of insecticides used as pest control agents in the present invention include: natural types: capsaicin, citronella oil, eucalyptus oil, etc.; neonicotinoid types: clothianidin, imidacloprid, acetamiprid, dinotefuran, thiamethoxam, nitenplum, thiacloprid, etc.; pyrethroid types: cyfluthrin, permethrin, deltamethrin, phenothrin, etofenprox, transfluthrin, resmethrin, etc.; organophosphate types: malathion, fenitrothion, chlorpyrifos, dichlorvos, etc.; carbamate types: carbaryl, propoxur, methomyl, etc.; phenylpyrazole types: fipronil, etc.; and others: spinosad, indoxacarb, pymetrozine, lufenuron, novaron, etc.

[0026] In this invention, the pest control effect refers to a synergistic pest control effect that exceeds the additive effect of combined use, as described above, against targets such as bacteria, molds, yeasts, wood-rotting fungi, algae, and insects. Examples of targets for control include bacteria, molds, yeasts, wood-rotting fungi, and algae. Examples of bacteria include Gram-negative bacilli such as Escherichia coli, Pseudomonas aeruginosa, and Serratia; Gram-positive bacilli such as Bacillus subtilis and Clostridium; Gram-negative cocci such as Branhamella; and Gram-positive cocci such as Staphylococcus aureus. Examples of fungi include zygomycetes such as the genera Absidia, Mucor, and Rhizopus; ascomycetes such as the genera Chaetomium, Eurotium, Neurospora, and Saccharomyces; and species such as Acremonium, Alternaria, and Aspergillus. Examples include imperfect fungi such as those belonging to the genera Aspergillus, Aureobasidium, Cladosporium, Fusarium, Penicillium, Phoma, Trichoderma, Rhodotorula, Candida, and Trichophyton.Examples of yeasts include protistascomycetes such as those of the genera Schizosaccharomyces, Protomyces, and Taphrina; euscomycetes such as those of the genera Endomyces; hemiscomycetes such as those of the genera Saccharomyces; incomplete forms of ascomycetic yeasts such as those of the genera Candida; heterobasidiella such as those of the genera Filobasidiella; incomplete forms of basidiomycete yeasts such as those of the genera Rhodotorula, Trichosporon, and Sporobolomyces; and basidiomycete yeasts such as those of the genera Rhodosporidium, Sporidiobolus, and Xanthophyllomyces. Examples of wood-decaying fungi include basidiomycetes such as the genera Coniophora, Trametes, Postia, Poria, Gloeophyllum, Lentinus, Paxillus, Fomitopsis, Pleurotus, Donkioporia, Serpula, Glenospora, Perenniporia, and Antrodia. Algae are plants that inhabit water and land, possess assimilated pigments, and live independently as a nutrient-rich life. Examples include cyanobacteria, gray algae, red algae, yellow flagellates, yellow-green algae, green algae, diatoms, brown flagellates, dinoflagellates, green flagellates, brown algae, zooxanthellae, and charophytes.

[0027] The present invention will be described in more detail below with reference to test examples, but the present invention is not limited to these examples. Test examples show that the agent for use in antiviral and / or antibacterial purposes of the present invention exhibits viral inhibitory and antibacterial effects.

[0028] <Example 1> A test was conducted to confirm the effect of suppressing enveloped viruses. (1) Test sample Galactaric acid was used as the test sample. This compound was a reagent manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. (2) Test sample solution 0.01 g of each test sample and 0.50 g of dimethyl sulfoxide (hereinafter referred to as "DMSO") were added to a sterile centrifuge tube to prepare test sample solution A with a concentration of 2% of the test sample. In addition, 0.05 g of test sample solution A and 0.45 g of DMSO were added to a sterile centrifuge tube to prepare test sample solution B with a concentration of 0.2% of the test sample. DMSO was used as the control test sample.

[0029] (3) Antiviral test of test sample solution <Confirmation test of effect on suppressing enveloped viruses> Influenza virus (ATCC VR-1679) 10 ８ TCID ５０ The test virus suspension was prepared by adjusting the concentration to 1 / mL. In a microtube containing a stirring bar, 0.05 mL of test sample solution A or test sample solution B, 0.85 mL of sterile water, and 0.1 mL of the test virus suspension were mixed, and the mixture, with a final concentration of approximately 0.1% or approximately 0.01%, was stirred for 24 hours. 50 μL of the mixture after stirring for the specified time was added to 450 μL of a drug inactivator (SCDLP liquid medium, manufactured by Eiken Chemical Co., Ltd.) and mixed. The inactivated mixture was then used to create 10-fold serial dilutions using dilution medium (E-MEM, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and tested in TCID using host cells (MDCK cells, ATCC CCL-34). ５０The viral infectivity titer was measured using the measurement method (Median Tissue Culture Infectious Dose). Similarly, the viral infectivity titer of the control test sample was also measured. Based on the viral infectivity titer, the viral inhibitory activity value (Mv) was calculated using the following formula: [Formula] Viral inhibitory activity value (Mv) = Ig(Vb) - Ig(Vc) Ig(Vb) = Common logarithm of the viral infectivity titer after mixing with the control test sample Ig(Vc) = Common logarithm of the viral infectivity titer after mixing with the test sample solution The obtained viral inhibitory activity value (Mv) and Ig(Vc) are summarized in Table 1 below. In Table 1, "%" means weight percent. Ig(Vb) was "6.50". A virus suppression activity value (Mv) of approximately "1" or higher was considered to indicate an effect in suppressing enveloped viruses, and a value of approximately "2" or higher was considered to indicate a practical effect in suppressing enveloped viruses.

[0030]

[0031] As shown in Table 1, the antiviral and / or antibacterial agent of the present invention exhibited a virus inhibitory activity value (Mv) of 5 or higher, far greater than "2," at both liquid concentrations of 0.1% and 0.01%, confirming that it exerts an extremely practical inhibitory effect against enveloped viruses. In particular, the remarkable antiviral inhibitory effect exhibited at a liquid concentration of 0.01% proved to be extremely useful.

[0032] <Example 2> A confirmation test for the non-enveloped virus inhibitory effect was conducted. A confirmation test for the virus inhibitory effect was carried out in the same manner as in Example 1 above, except that the influenza virus in the test virus suspension was changed to feline calicivirus (ATCC VR-782), the E-MEM dilution medium was changed to RPMI-1640 (manufactured by Fujifilm Wako Pure Chemical Corporation), and the host cell MDCK cells were changed to CRFK cells (ATCC CCL-94). Based on the measured viral infectivity titer, the virus suppression activity value (Mv) was calculated by the above calculation formula. The obtained virus suppression activity value (Mv) is summarized together with Ig(Vc) in Table 2 below. "%" in Table 2 means % by weight. Ig(Vb) was "5.50". When the virus suppression activity value (Mv) is approximately "1" or more, it was judged to have a non-enveloped virus inhibitory effect, and when it is approximately "2" or more, it was judged to have a practical non-enveloped virus inhibitory effect.

[0033]

[0034] As shown in Table 2, the agent for antiviral and / or antibacterial use according to the present invention has a virus suppression activity value (Mv) of 4, which is far larger than "2", at a concentration of 0.1% in liquid, and it was confirmed that the agent exerts an extremely practical inhibitory effect against non-enveloped viruses.

[0035] <Example 3> A confirmation test for the virus inhibitory effect of a coating film obtained by adding the agent for antiviral and / or antibacterial use according to the present invention to a coating material was conducted. (1) Test specimen Galactaric acid was used as a test specimen. A reagent manufactured by Fujifilm Wako Pure Chemical Corporation was used for this compound. (2) Test specimen coating film 0.464 g of the above test specimen was added to 19.536 g of an acrylic resin emulsion (trade name "Ultrasol FCE-20", manufactured by Aica Kogyo Co., Ltd., solid content 46.40%), the mixture was uniformly mixed using a mortar and pestle, and formulated so that the content of the above test specimen in the dried coating film would be 5% by weight, to prepare a coating material. The obtained coating for antiviral and / or antibacterial use was applied onto the surface of a PET plate with a bar coater (No. 22) such that the wet coating film had a thickness of 50 µm, dried at room temperature for 18 hours, and cut (5 cm × 5 cm) with a cutter, to obtain a test specimen coating film in which the content of the above test specimen in the dried coating film for use in the virus inhibitory effect confirmation test was 5% by weight. Further, a comparative test specimen coating film was obtained by preparation in the same manner, except that the above test specimen, which is the agent for antiviral and / or antibacterial use according to the present invention, was not added. In the method for producing the above test specimen coating film, 0.2784 g and 0.0928 g of the above test specimen were added to 19.7216 g and 19.9072 g of an acrylic resin emulsion (trade name "Ultrasol FCE-20", manufactured by Aica Kogyo Co., Ltd., solid content 46.40%), respectively, the mixture was uniformly mixed using a mortar and pestle, and test specimen coating films were prepared in the same manner except that the mixture was formulated so that the content of the above test specimen in the dried coating film would be 3% by weight and 1% by weight, respectively.

[0036] (3) Virus inhibitory effect confirmation test The virus inhibitory effect was confirmed in accordance with a test method for evaluating the antiviral effect on non-absorbent surfaces such as plastic products and ceramic products (ISO 21702). Influenza virus (ATCC VR-1679) and feline calicivirus (ATCC VR-782) were each adjusted to 10 ７ TCID ５０The preparation adjusted to / mL was used as a test virus suspension. 0.4 mL of the test virus suspension was dropped onto a test specimen coating film, the resulting material covered with a 4 cm square polyethylene film was allowed to stand at 25°C for 24 hours. After standing still, the virus on the test piece was washed out and recovered, and the virus infectious titer was determined by TCID ５０ measurement method (Median Tissue Culture Infectious Dose). The virus infectious titer was also measured in the same manner for a comparative test specimen coating film. Based on the virus infectious titer, the antiviral activity value (R) was calculated by the following calculation formula. [Calculation formula] Antiviral activity value (R) = U ｔ - A ｔ U ｔ = average of common logarithms of virus infectious titer after 24 hours of standing on comparative test specimen coating film (TCID ５０ / cm ２ ) A ｔ = average of common logarithms of virus infectious titer after 24 hours of standing on test specimen coating film (TCID ５０ / cm ２ ) Together with the obtained antiviral activity value (R), U ｔ and A ｔ , the results against influenza virus / feline calicivirus for test specimen coating films in which the content of the aforementioned test specimen in the dried coating film is 5% by weight are summarized in Table 3 below, the results against influenza virus / feline calicivirus for test specimen coating films in which the content of the aforementioned test specimen in the dried coating film is 3% by weight are summarized in Table 4 below, and the results against influenza virus for test specimen coating films in which the content of the aforementioned test specimen in the dried coating film is 1% by weight are summarized in Table 5 below. In Tables 3 to 5, "%" means percent by weight. When the antiviral activity value (R) is approximately "1" or more, it was judged to have an enveloped virus / non-enveloped virus inhibitory effect, and when it is approximately "2" or more, it was judged to have a practical enveloped virus / non-enveloped virus inhibitory effect.

[0037]

[0038]

[0039]

[0040] As shown in Tables 3 to 5, it was confirmed that coating films obtained by adding the antiviral and / or antibacterial agent of the present invention to paint also exhibit excellent antiviral activity. The antiviral activity value (R) was 5, which is far greater than "2" for enveloped viruses, was confirmed to exhibit an extremely practical inhibitory effect, even at total formulation amounts of 5%, 3%, and 1% by weight of the above test sample in the coating film when dry, and especially at the low formulation amount of 1% by weight of the above test sample in the coating film when dry. Furthermore, at formulation amounts of 5% and 3% by weight of the above test sample in the coating film when dry, the antiviral activity value (R) was 4 or higher, which is far greater than "2" for non-enveloped viruses, and it was confirmed that this also exhibits an extremely practical inhibitory effect. In Examples 1 and 2, the antiviral and / or antibacterial agent of the present invention comes into direct contact with the virus in a liquid, whereas in Example 3, the antiviral and / or antibacterial agent of the present invention is present in a coating film. Therefore, although the opportunity for contact with the virus is reduced compared to Examples 1 and 2, it exhibits an excellent virus-suppressing effect as shown in Tables 3 to 5, making it extremely useful, for example, in industrial applications applied to various industrial products and materials.

[0041] <Example 4> A test was conducted to confirm the antibacterial effect of the agent for use as an antiviral and / or antibacterial agent of the present invention. (1) Test sample The following compound A was used as test sample A. A: Galactaric acid: Manufactured by Fujifilm Wako Pure Chemical Industries Ltd. The following compounds B1 to B19 were used as test samples B, which are known pest control agents to be used in combination. B1: Carbendazim (1H-benzimidazole-2-ylcarbamate methyl, hereinafter referred to as "MBC"): Manufactured by Tokyo Chemical Industry Co., Ltd. B2: N-butylcarbamate 3-iodo-2-propynyl (hereinafter referred to as "IPBC"): Manufactured by Tokyo Chemical Industry Co., Ltd. B3: Oxolinic acid: Manufactured by Fujifilm Wako Pure Chemical Corporation B4: Norfloxacin: Manufactured by Fujifilm Wako Pure Chemical Corporation B5: Pyrithione zinc (hereinafter referred to as "ZPT"): Manufactured by Fujifilm Wako Pure Chemical Corporation B6: Benzoic acid: Manufactured by Fujifilm Wako Pure Chemical Corporation B7: Butylparaben: Manufactured by Fujifilm Wako Pure Chemical Corporation B8: Phenoxyethanol: Manufactured by Fujifilm Wako Pure Chemical Corporation B9: 2-methyl-4-isothiazolin-3-one (hereinafter referred to as "H-MIT"): Manufactured by Fujifilm Wako Pure Chemical Corporation B10: 2-n-octyl-4-isothiazolin-3-one (hereinafter referred to as "OIT"): Manufactured by Tokyo Chemical Industry Co., Ltd. B11: 2-bromo-2-nitro-1,3-propanediol (hereinafter referred to as "BNPD"): Manufactured by Fujifilm Wako Pure Chemical Corporation B12: Sulfadiazine: Manufactured by Fujifilm Wako Pure Chemical Corporation B13: Chloramphenicol: Manufactured by Fujifilm Wako Pure Chemical Corporation B14: Benzylpenicillin potassium: Manufactured by Fujifilm Wako Pure Chemical Corporation B15: Kanamycin sulfate: Manufactured by Fujifilm Wako Pure Chemical Corporation B16: Tebuconazole: Manufactured by Tokyo Chemical Industry Co., Ltd. B17: B18: Benzalkonium chloride: Manufactured by Fujifilm Wako Pure Chemical Corporation B18: 1,2-Dodecanediol: Manufactured by Tokyo Chemical Industry Co., Ltd. B19: Paraphenylphenol (hereinafter referred to as "PPP"): Manufactured by Fujifilm Wako Pure Chemical Corporation (2) Test sample solution A test sample solution was prepared using 5 parts by weight of test sample A, 5 parts by weight of test sample B1, and purified water to make a total volume of 100 parts by weight, with a ratio of test sample A:test sample B1 = 50:50.Other test sample solutions were prepared according to the above method for preparing the test sample solution of "Test Sample A:Test Sample B1 = 50:50" in accordance with the mixing ratio "(a):(b)" of test sample A and test sample B described in Tables 6 to 14 below. (3) Method for testing antibacterial activity (antibacterial) 1 Dispense 1 mL of the above test sample and 9 mL of glucose broth medium (pH 6.0) into petri dishes, and prepare glucose broth medium by diluting the above test sample solution 10 times, then allow to stand and solidify. Then, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), inoculate with suspensions of bacteria described in Tables 7 to 11, 13, and 14, and culture at 33°C for 18 hours. After that, observe the growth of each bacterium after culture and calculate the minimum inhibitory concentration (MIC: μg / mL) for each. Each test was performed 5 times, and the average value was used as the MIC value. (4) Test method for antibacterial activity (antifungal, antiyeast) 2 Dispense 1 mL of the above test sample and 9 mL of glucose broth medium (pH 6.0) into a petri dish, and prepare glucose broth medium by diluting the above test sample 10 times, then allow to stand and solidify. Then, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), inoculate with a mold suspension or yeast suspension containing the mold or yeast described in Tables 6, 7, 9-14, and culture at 33°C for 18 hours and at 28°C for 2 days. After that, observe the growth of each fungus after culture and calculate the minimum inhibitory concentration (MIC: μg / mL) for each. Each test was performed 5 times, and the average value was used as the MIC value.

[0042] (5) Method for evaluating antibacterial activity The antibacterial activity was evaluated by calculating the theoretical value of MIC when test samples A and B were used together using the following formula, based on the MIC values ​​obtained when each test sample A and B were used individually, and then comparing the actually measured MIC value with these. If the measured value of MIC is smaller than the calculated theoretical value, that is, if "measured value / theoretical value" is less than 1, it can be said that the antibacterial activity is enhanced by the algebraic sum of the values ​​obtained when each of the above components is used individually, and therefore a synergistic effect is observed. Theoretical value of MIC = 1 / (x / C) Ａ +y / C Ｂ ) C Ａ MIC value C when test sample A is used alone Ｂ;MIC value when each of the test samples B is used individually x;Percentage (by weight) of test sample A in the antibacterial components y;Percentage (by weight) of test sample B in the antibacterial components Tables 6 to 12 below show galactaric acid as test sample A and MBC (B1) (Table 6), IPBC (B2) (Table 7), oxolinic acid (B3) and norfloxacin (B4) (Table 8), ZPT (B5) (Table 9), benzoic acid (B6) (Table 10), butylparaben (B7) (Table 11), phenoxyethanol (B8) (Table 12), H-MIT (B9), OIT (B10), BNPD (B11), and sulfadiazine (B12) as test samples B Table 13 and Table 14 show the mixing ratio of test sample A and test sample B "(a):(b)" for the combined use of chloramphenicol (B13) (Table 13), benzylpenicillin potassium (B14), kanamycin sulfate (B15), tebuconazole (B16), benzalkonium chloride (B17), 1,2-dodecanediol (B18), and PPP (B19) (Table 14), and the evaluation results, "measured value," "theoretical value," and "measured value / theoretical value," are all shown together. Note that in Tables 13 and 14, " / " is displayed for the "measured value," "theoretical value," and "measured value / theoretical value" columns, indicating that the test was not performed. In addition, in Tables 6, 7, 9-11, and 13, if the measured value of compound A alone is ">10000", then "C" in the formula for calculating the theoretical value is omitted. Ａ The value was calculated as "10000". Looking at the calculation formula for the "theoretical value of MIC" above, "C Ａ By setting the value of "MIC" to a smaller value than the actual measured value, the "theoretical value of MIC" becomes smaller than when the actual measured value is used, and the "measured value / theoretical value" becomes larger than when the actual measured value is used. Therefore, there is no problem with the evaluation in Tables 6, 7, 9-11, and 13 that a synergistic effect is observed.

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] Table 12 shows that the measured values ​​for compound A and compound B8 alone are greater than 10,000 and 1,000, respectively. Since the measured value for test example 29, in which compound A and compound B8 are used in combination, is "1,000", it is clear that a synergistic effect greater than the additive effect was achieved by using them together, without even needing to calculate "measured value / theoretical value".

[0050]

[0051]

[0052] As shown in Tables 6 to 14, the antiviral and / or antibacterial agents of the present invention exhibit antibacterial activity on their own, but it has been confirmed that when used in combination with known pest control agents, they exhibit a synergistic pest control effect that exceeds the additive effect. The antiviral and / or antibacterial agents of the present invention are extremely useful because, when used in combination with known pest control agents, they can reduce the amount of known pest control agents used.

[0053] The antiviral and / or antibacterial agent of the present invention is extremely useful because it contains galactaric acid, which has excellent safety, as an active ingredient, and exhibits excellent virus-suppressing and / or antibacterial effects. In particular, it is useful in industrial applications applied to various industrial products and materials because it can provide excellent safety and excellent virus-suppressing and / or antibacterial effects.

Claims

1. An agent for antiviral and / or antibacterial use, comprising galactaric acid and / or its salts as an active ingredient.

2. A product having antiviral and / or antibacterial properties, comprising the agent for use as described in claim 1.

3. A method for inhibiting and / or inhibiting viruses using an agent for antiviral and / or antibacterial purposes described in claim 1, but not in humans.

4. A method for producing an antiviral and / or antibacterial treated article, comprising incorporating the agent for use as described in claim 1 into the article or coating it on the surface of the article.

5. An antiviral and pest control composition comprising the antiviral and / or antibacterial agent described in claim 1 and a pest control agent.

6. An antiviral and pest control product containing the antiviral and pest control composition described in claim 5.

7. A method for producing an article that has been treated with antiviral and pest control, comprising incorporating the antiviral and pest control composition described in claim 5 into the article or coating it on the surface of the article.

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