Antibacterial or antiviral agent, antibacterial or antiviral material in which an antibacterial or antiviral agent is carried on a substrate, or antibacterial or antiviral paint containing an antibacterial or antiviral agent

Abstract

To provide an antibacterial agent or antiviral agent that has excellent antibacterial activity and antiviral activity, an antibacterial material or antiviral material in which the antibacterial agent or antiviral agent is supported on a substrate, or an antibacterial paint or antiviral paint that contains antibacterial agent or antiviral agent.SOLUTION: Provided is an antibacterial or antiviral agent that contains a metal complex or an adduct thereof represented by the following formula (1) or (2) (in the formula, M is a metal atom, D1 to D28 are each independently a nitrogen atom, a sulfur atom or a carbon atom, and when D1 to D28 are a carbon atom, the carbon atom may be bonded to hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aryl group, alkylsulfonyl group, alkoxy group or alkylthio group.).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an antibacterial or antiviral agent, an antibacterial or antiviral material in which the antibacterial or antiviral agent is carried on a substrate, or an antibacterial or antiviral paint containing the antibacterial or antiviral agent. [Background technology]

[0002] In recent years, interest in antibacterial and antiviral properties has grown as a countermeasure against COVID-19 and other diseases. Various measures have been taken to prevent infection, but there is also a demand for everyday household products with antibacterial and antiviral properties. There is also growing demand for masks, a typical infection prevention measure, that have antibacterial and antiviral properties.

[0003] Antibacterial and antiviral agents containing metal phthalocyanines as active ingredients are known. Patent Document 1 discloses a fiber material carrying an allergen decomposing agent containing a specific metal phthalocyanine derivative as an active ingredient. Patent Document 2 discloses an antiviral agent made of a specific metal phthalocyanine.

[0004] However, the antibacterial and antiviral activities of these antibacterial and antiviral agents containing metal phthalocyanines as active ingredients are sometimes insufficient. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2006-144219 [Patent Document 2] Japanese Patent Application Laid-Open No. 2010-30983 Summary of the Invention [Problem to be solved by the invention]

[0006] The present inventors have discovered a novel metal phthalocyanine compound having excellent antibacterial and antiviral activities and have completed the present invention. That is, an object of the present invention is to provide an antibacterial or antiviral agent having excellent antibacterial and antiviral activities, an antibacterial or antiviral material in which an antibacterial or antiviral agent is supported on a substrate, or an antibacterial or antiviral paint containing an antibacterial or antiviral agent. [Means for solving the problem]

[0007] As a result of extensive research into the above-mentioned problems, the present inventors unexpectedly discovered that the use of a metal complex or an adduct thereof having a specific structure has excellent antibacterial and antiviral activities, and thus arrived at the present invention.

[0008] The object of the present invention is to provide a compound having the following formula (1) or (2): [ka] (In the formula, M is a metal atom, D 1 From D 28 are each independently a nitrogen atom, a sulfur atom, or a carbon atom, D 1 From D 28 is a carbon atom, each of the carbon atoms may independently be bonded to a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylsulfonyl group, an alkoxy group, or an alkylthio group. This is achieved by an antibacterial or antiviral agent comprising a metal complex or an adduct thereof represented by the formula:

[0009] In the formula (1) or (2), M is preferably a manganese atom, an iron atom, a cobalt atom, a nickel atom, a copper atom, or a zinc atom.

[0010] In the formula (1) or (2), D 1 From D 16is preferably a nitrogen atom or a carbon atom, and D 17 From D 28 is preferably a sulfur atom or a carbon atom.

[0011] The metal complex or adduct thereof has the following formula: [ka] [ka] [ka] [ka] [ka] It is preferable that the formula be represented by the following formula:

[0012] The present invention also relates to an antibacterial or antiviral material in which the antibacterial or antiviral agent of the present invention is carried on a substrate.

[0013] The substrate is preferably a fiber or paper, and the fiber is preferably a natural fiber, a recycled fiber, a semi-synthetic fiber, or a synthetic fiber.

[0014] The present invention also relates to antibacterial or antiviral paints comprising the antibacterial or antiviral agent of the present invention. [Effects of the Invention]

[0015] According to the present invention, by using the antibacterial agent or antiviral agent of the present invention, excellent antibacterial activity and antiviral activity can be provided.

[0016] The present invention can also provide an antibacterial material and an antiviral material, or an antibacterial paint or an antiviral paint, containing an antibacterial agent and an antiviral agent having excellent antibacterial activity and antiviral activity. DETAILED DESCRIPTION OF THE INVENTION

[0017] [Metal complexes or their adducts] The antibacterial or antiviral agent of the present invention contains a metal complex or an adduct thereof, and the metal complex or the adduct thereof is represented by the following formula (1) or (2): [ka] (In the formula, M is a metal atom, D 1 From D 28 are each independently a nitrogen atom, a sulfur atom, or a carbon atom, D 1 From D 28 is a carbon atom, each of the carbon atoms may independently be bonded to a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylsulfonyl group, an alkoxy group, or an alkylthio group. It is expressed as:

[0018] The bond between a nitrogen atom and M means that the nitrogen atom is coordinated to M. A halogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 8 carbon atoms may further be bonded to M as a ligand. An anionic counter ion may also be present to make M electrically neutral. Furthermore, M may exist as an adduct to which an electrically neutral molecule is added.

[0019] The valence of M is not particularly limited. A halogen atom, a hydroxyl group, or an (alkyloxy)alkoxy group having 1 to 8 carbon atoms may be bonded as a ligand (for example, an axial ligand) so that the metal complex or its adduct is electrically neutral, and an anionic counter ion may be present. Examples of anionic counter ions include halide ions, hydroxide ions, nitrate ions, and sulfate ions. The alkyl group in the (alkyloxy)alkoxy group having 1 to 8 carbon atoms may have a linear, branched, or cyclic structure.

[0020] Examples of M include a scandium atom, a titanium atom, a vanadium atom, a chromium atom, a manganese atom, an iron atom, a cobalt atom, a nickel atom, a copper atom, a zinc atom, a yttrium atom, a zirconium atom, a niobium atom, a ruthenium atom, a rhodium atom, a palladium atom, a lanthanum atom, a cerium atom, a praseodymium atom, a neodymium atom, a promethium atom, a samarium atom, a europium atom, a gadolinium atom, a terbium atom, a dysprosium atom, a holmium atom, an erbium atom, a thulium atom, a ytterbium atom, a lutetium atom, an actinium atom, a thorium atom, a protactinium atom, a uranium atom, a neptunium atom, a plutonium atom, americium atom, a curium atom, a berkelium atom, a californium atom, an einsteinium atom, a fermium atom, a mendelevium atom, a nobelium atom, and a lawrencium atom. Among these, M is preferably a manganese atom, iron atom, cobalt atom, nickel atom, copper atom, or zinc atom, and more preferably an iron atom, cobalt atom, nickel atom, or copper atom.

[0021] In the present invention, halogen atoms include fluorine, chlorine, bromine, and iodine.

[0022] In the present invention, the alkyl group refers to a linear or branched monovalent hydrocarbon group. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 6. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, and an n-hexyl group.

[0023] In the present invention, the cycloalkyl group refers to a cyclic monovalent hydrocarbon group. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and even more preferably 3 to 6 carbon atoms. Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, and a 2,2-dimethylcyclopropyl group.

[0024] In the present invention, the alkenyl group refers to a linear or branched monovalent hydrocarbon group containing a double bond. The alkenyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and even more preferably 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0025] In the present invention, the term "alkynyl group" refers to a linear or branched monovalent hydrocarbon group containing a triple bond. The number of carbon atoms in the alkynyl group is preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 6. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a (1-butynyl group) 1-butyn-1-yl group, a (2-butynyl group) 2-butyn-1-yl group, a (3-butynyl group) 3-butyn-1-yl group, a (1-methyl-2-propynyl group) 1-methyl-2-propyn-1-yl group, a (2-methyl-3-butynyl group) 2-methyl-3-butyn-2yl group, a (1-pentynyl group) 1-pentyn-1-yl group, a (2-pentynyl group) Examples include (1-pentynyl) 2-pentyn-1-yl, (3-pentynyl) 3-pentyn-2-yl, (4-pentynyl) 4-pentyn-1-yl, 1-methyl-2-butynyl (1-methyl-2-butyn-1-yl), (2-methyl-3-pentynyl) 2-methyl-3-pentyn-1-yl, (1-hexynyl) 1-hexyn-1-yl, and (1,1-dimethyl-2-butynyl) 1,1-dimethyl-2-butyn-1-yl.

[0026] In the present invention, the term "aryl group" refers to a monovalent aromatic hydrocarbon group. The number of carbon atoms in the aryl group is preferably 6 to 40, and more preferably 6 to 30. Examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a benzophenanthryl group, a benzanthracenyl group, a chrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzanthracenyl group, a perylenyl group, and a helicenyl group.

[0027] In the present invention, the term "alkylsulfonyl group" refers to a monovalent group in which an alkyl group is bonded to a sulfonyl group. The alkyl group in the alkylsulfonyl group can be any of the groups described above as "alkyl group." The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 6. Examples of alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, tert-pentylsulfonyl, neopentylsulfonyl, 2,3-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1-methylbutylsulfonyl, n-hexylsulfonyl, isohexylsulfonyl, and 1,1,2-trimethylpropylsulfonyl.

[0028] In the present invention, an alkoxy group refers to a monovalent group to which a hydrocarbon group is bonded via an ether bond. The number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 6. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and an isohexyloxy group.

[0029] In the present invention, the alkylthio group refers to a group in which the oxygen atom in the ether bond of an alkoxy group is substituted with a sulfur atom. The number of carbon atoms in the alkylthio group is preferably 1 to 20, more preferably 1 to 16, and even more preferably 1 to 12. Examples of the alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an isopropylthio group.

[0030] The alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aryl group, alkylsulfonyl group, alkoxy group, and alkylthio group may be unsubstituted, or may be substituted with one or more substituents such as halogen, alkyl group, alkenyl group, alkynyl group, aryl group, alkoxy group, alkylthio group, cyano group, carbonyl group, carboxyl group, amino group, nitro group, silyl group, and sulfo group.

[0031] D 1 From D 16 is preferably a nitrogen atom or a carbon atom, and D 17 From D 28 is preferably a sulfur atom or a carbon atom. 1 From D 16 The number of nitrogen atoms in the group is preferably 2 to 12, and more preferably 4 to 8. 17 From D 28 The number of sulfur atoms is preferably 2 to 10, and more preferably 4 to 8.

[0032] Preferably, the metal complex or adduct thereof of the present invention is a compound represented by the following formula:

[0033] [ka] [ka] [ka] [ka] [ka]

[0034] The method for producing the metal complex or its adduct is not particularly limited, but an example thereof is a method in which a dicyano compound such as pyridine-2,3-dicarbonitrile and a metal atom are heated in an alcohol solvent in the presence of a basic substance, examples of which include inorganic bases such as potassium carbonate, sodium carbonate, calcium carbonate, sodium bicarbonate, and sodium acetate, and organic bases such as triethylamine, tributylamine, and diazabicycloundecene.

[0035] [Antibacterial and antiviral agents] The antibacterial or antiviral agent of the present invention contains a metal complex or an adduct thereof as an active ingredient, and may contain only one type of metal complex or an adduct thereof, or may contain a combination of two or more types of metal complexes or adducts thereof.

[0036] In the present invention, "antibacterial" means killing or eliminating bacteria and fungi, or inhibiting the development, growth, or proliferation of bacteria and fungi. "Antiviral" means inactivating or inhibiting the proliferation of pathogenic viruses.

[0037] The antibacterial or antiviral agent of the present invention can exhibit antibacterial activity or antiviral activity against, for example, bacteria such as gram-negative bacteria such as Klebsiella pneumoniae and gram-positive bacteria such as Staphylococcus aureus, fungi such as cryptococcosis and tinea fungi, or viruses such as enveloped viruses such as influenza virus and non-enveloped viruses such as feline calicivirus.

[0038] The concentration of the metal complex or adduct thereof contained in the antibacterial or antiviral agent of the present invention is not particularly limited, but may be preferably 0.001 mg / mL or more, more preferably 0.01 mg / mL or more, and most preferably 0.1 mg / mL or more, and may be preferably 10 mg / mL or less, more preferably 5 mg / mL or less, and most preferably 3 mg / mL or less. When the concentration of the metal complex or adduct thereof is equal to or greater than the above-mentioned lower limit, excellent antibacterial activity and antiviral activity can be obtained.

[0039] The solvent for the antibacterial or antiviral agent is not particularly limited, and may be an inorganic solvent such as water, or an organic solvent. Specific examples of organic solvents include alcohols such as methanol, ethanol, propanol, isopropanol (2-propanol), and 1-hexanol; dimethyl sulfoxide; tetrahydrofuran; aprotic polar solvents such as N-methylpyrrolidone, dimethylformamide, and acetone; and nonpolar solvents such as chloroform, dichloromethane, 1,4-dioxane, benzene, and toluene. One solvent may be used alone, or two or more solvents may be used in combination.

[0040] The antibacterial and antiviral agents of the present invention may contain any additive as an optional component. The additive is not particularly limited as long as it does not inhibit the antibacterial and antiviral effects of the present invention, and examples thereof include surfactants, dispersants, thickeners, pH adjusters, antioxidants, moisturizers, colorants, UV absorbers, stabilizers, and fragrances.

[0041] Furthermore, the antibacterial and antiviral agents of the present invention may contain an antibacterial or antiviral substance other than the metal complex or its adduct.

[0042] The form of the antibacterial and antiviral agent of the present invention is not particularly limited, and may be in the form of a liquid, cream, ointment, gel, wax, spray, or the like.

[0043] [Antibacterial and antiviral materials] In one embodiment, the present invention relates to an antibacterial or antiviral material in which the antibacterial or antiviral agent of the present invention is supported on a substrate. For example, the antibacterial or antiviral agent can be supported on a substrate by applying the antibacterial or antiviral agent to the surface of the substrate or by immersing the substrate in the antibacterial or antiviral agent and then removing the solvent.

[0044] The substrate on which the antibacterial or antiviral agent is carried is not particularly limited, and may be fiber or paper, and may be formed into thread, fabric, web, nonwoven fabric, net, etc. The fiber may be natural fiber, regenerated fiber, semi-synthetic fiber, or synthetic fiber. Natural fibers include plant fibers such as hemp and cotton, and animal fibers such as wool and silk. Regenerated fibers include rayon and cupra. Semi-synthetic fibers include acetate and triacetate. Synthetic fibers include polyamide fibers, polyester fibers, polyacrylic fibers, polyvinyl alcohol fibers, polyolefin fibers, and polyurethane fibers.

[0045] The antibacterial or antiviral material of the present invention can be used, without particular limitation, in products that require antibacterial or antiviral properties, such as clothing, bedding such as sheets, packaging materials, architectural interior materials such as curtains and wallpaper, sanitary products such as masks, daily necessities such as towels, interior materials for vehicles, mouthwash, and toothpaste.

[0046] [Antibacterial and antiviral paints] In one embodiment, the present invention relates to an antibacterial paint or antiviral paint comprising the antibacterial agent or antiviral agent of the present invention. The metal complex or adduct thereof contained in the antibacterial agent or antiviral agent of the present invention may itself act as a colorant, or another colorant may be added to the antibacterial agent or antiviral agent of the present invention to form a paint.

[0047] The antibacterial paint or antiviral paint of the present invention can be used without any particular limitation on the interior and exterior wall surfaces of buildings such as ordinary houses. [Example]

[0048] The present invention will be described in more detail below using examples and comparative examples, but the scope of the present invention is not limited to the examples.

[0049] (Preparation of metal complexes or their adducts) Synthesis Example 1 Synthesis of compound (16) 10 mL of 1-pentanol was added to 1.29 g of 2,3-dicyanopyridine and 390 mg of anhydrous cobalt chloride, and 0.1 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene was added thereto, followed by heating to 155° C. and reaction overnight.

[0050] 20 mL of N,N-dimethylformamide was added to the reaction mixture, and the mixture was stirred at 155°C for 30 minutes. After cooling to room temperature, the precipitated solid was collected by vacuum filtration, washed with N,N-dimethylformamide, water, methanol, and acetone, and then dried to obtain the target product. Yield: 0.75 g.

[0051] Synthesis Example 2: Synthesis of Compound (8) (1) Synthesis of 5,6-dimethyl-2,3-pyrazinedicarbonitrile 10 mL of acetic acid was added to 3.24 g of diaminomaleonitrile, and 2.64 mL of diacetyl was added. The mixture was heated under reflux for 1 hour. Upon cooling, crystals precipitated. 10 mL of water was added, and the crystals were collected by filtration. After washing with water, the crystals were dried to obtain the target product. Yield: 4.45 g.

[0052] (2) Synthesis of compound (9) 30 mL of 1-pentanol was added to 6.32 g of 5,6-dimethyl-2,3-pyrazinedicarbonitrile, followed by 1.78 g of anhydrous ferric chloride and 1.9 mL of 4-methylpyridine. The mixture was heated in an oil bath set to 145°C and allowed to react. After 5 hours of reaction, the heating was stopped. When the temperature of the reaction solution reached 100°C, 30 mL of methanol was added dropwise. After cooling to room temperature, the mixture was filtered under reduced pressure, carefully washed with water and methanol, then washed with acetone, and dried to obtain the desired product. Yield: 6.8 g.

[0053] (3) Synthesis of compound (8) 1.8 g of compound (9) was taken, 20 mL of concentrated sulfuric acid was added, and the mixture was stirred at room temperature. After 1 hour, the mixture was added dropwise to 200 mL of water. The precipitated solid was separated by centrifugation, and the resulting solid was washed with water and methanol using a centrifuge to obtain compound (8). Yield: 1.0 g.

[0054] (Preparation of samples for antibacterial and antiviral tests) Japanese Pharmacopoeia gauze was immersed in the prepared dimethyl sulfoxide (DMSO) solutions (1 mg / mL) of compound (16) and compound (8), rinsed with methanol, and dried by evaporating the solvent. Untreated Japanese Pharmacopoeia gauze was also prepared as a control.

[0055] (Antibacterial test) The test was conducted in accordance with JIS L 1902:2015 "Test methods for antibacterial properties and antibacterial effects of textile products." Specifically, a bacterial solution was prepared in 1 / 20 nutrient medium, and the bacterial solution was inoculated into a sample placed in a vial, after which the vial was capped. The inoculated sample was cultured at 37°C for 18 hours, and the viable bacterial count was measured immediately after inoculation and after 18 hours of culture.

[0056] The following three types of test bacteria were used: (1) Staphylococcus aureus NBRC 12732 (2) Klebsiella pneumoniae NBRC 13277 (3) Methicillin-resistant Staphylococcus aureus IID 1677

[0057] The number of viable bacteria was measured by the pour plate culture method, and the antibacterial activity value was calculated using the following formula.

[0058] Antibacterial activity value = (log C t -logC0)-(logT t -logT0)

[0059] In the calculation formula, C t is the number of viable bacteria on the standard cloth after 18 hours of incubation, C0 is the number of viable bacteria on the standard cloth immediately after inoculation, T t represents the number of viable bacteria on the antibacterial fabric after 18 hours of incubation, and T0 represents the number of viable bacteria on the antibacterial fabric immediately after inoculation.

[0060] Generally, an antibacterial activity value of 2.0 or higher indicates an antibacterial effect, and a value of 3.0 or higher indicates a strong antibacterial effect. The results of determining the antibacterial activity values ​​of fabrics treated with compounds (16) and (8) against three types of test bacteria (1) to (3) are shown in Tables 1 and 2 below.

[0061] [Table 1]

[0062] [Table 2]

[0063] As shown in Tables 1 and 2, both compound (16) and compound (8) were found to have a significant effect in reducing the viable bacterial count against all bacterial species, including Staphylococcus aureus, Klebsiella pneumoniae, and methicillin-resistant Staphylococcus aureus. 18 hours after inoculation, the viable bacterial count on the control fabric had increased by approximately 1,000 times, whereas on the fabrics treated with compound (16) and compound (8), the viable bacterial count had decreased to approximately 1 / 1,000 to 1 / 100 of the level immediately after inoculation.

[0064] (Antiviral test) The tests were carried out in accordance with JIS L 1922 "Testing Methods for Antiviral Activity of Textile Products." Specifically, for influenza A virus (H3N2) and influenza A virus (H1N1), host cells, MDCK cells (canine kidney-derived cells), were infected with the virus, and after culturing, the cell debris was removed by centrifugation to obtain a virus suspension. For feline calicivirus (F-9), CRFK cells (feline kidney-derived cells) were infected with the virus, and after culturing, the cell debris was removed by centrifugation to obtain a virus suspension. The obtained virus suspension was diluted 10-fold with sterile distilled water to obtain a concentration of 1 to 5 × 10 7 The test virus suspension was adjusted to PFU / mL.

[0065] Each sample was inoculated with 0.2 mL of the test virus suspension, and after 2 hours at 25°C, 20 mL of washing solution was added, and the sample was stirred with a vortex mixer to wash out the virus from the sample.

[0066] The following three types of test viruses were used: (1) Influenza A virus (H3N2) A / Hong Kong / 8 / 68; TC adapted from ATCC VR-1679 (2) Influenza A virus (H1N1) A / PR / 8 / 34; TC adapted from ATCC VR-1469 (3) Feline calicivirus (F-9); Strain: F-9 ATCC VR-782

[0067] The infectivity titer was measured by the plaque assay method, and the antiviral activity value was calculated using the following formula.

[0068] Antiviral activity value = logV a -logV c

[0069] In the calculation formula, V a is the virus infectivity titer of the standard cloth immediately after inoculation, V c indicates the viral infectivity of the antiviral treated fabric after 2 hours of action.

[0070] The antiviral activity values ​​of the fabric treated with compound (16) against the three test viruses (1) to (3) are shown in Table 3 below.

[0071] [Table 3]

[0072] As shown in Table 3, compound (16) was found to have a viral infectivity reducing effect against all of influenza A virus (H3N2), influenza A virus (H1N1), and feline calicivirus (F-9). [Industrial Applicability]

[0073] The antibacterial or antiviral agent of the present invention is useful because it has excellent antibacterial and antiviral activity against various fungi and viruses. Furthermore, by supporting the antibacterial or antiviral agent of the present invention on a substrate, an antibacterial material or antiviral material exhibiting excellent antibacterial and antiviral activity can be obtained. Furthermore, by including the antibacterial or antiviral agent of the present invention, an antibacterial paint or antiviral paint exhibiting excellent antibacterial and antiviral activity can be obtained.

Claims

1. The following formula: 【Chemistry 1】 【Chemistry 2】 An antibacterial or antiviral agent comprising a metal complex or an adduct thereof represented by the formula:

2. An antibacterial or antiviral material comprising the antibacterial or antiviral agent according to claim 1 carried on a substrate.

3. The antibacterial or antiviral material according to claim 2 , wherein the substrate is a fiber or paper.

4. 4. The antibacterial or antiviral material of claim 3, wherein the fibers are natural, regenerated, semi-synthetic, or synthetic fibers.

5. An antibacterial or antiviral paint comprising the antibacterial or antiviral agent according to claim 1.

Images