Antimicrobial composition and antimicrobial active agent

Abstract

To provide an antimicrobial composition which has water solubility and exhibits superior antibacterial effects against Gram-positive bacteria.SOLUTION: An antimicrobial composition of the present disclosure contains a diiodomethane compound (A), a cyclodextrin derivative (B), and a compound (C), wherein the compound (C) includes at least one selected from the group consisting of pyrrolidones, organic acids, terpenes, urea and urea derivatives, alcohols, esters, chelating compounds, antioxidants, surfactants, and thioglycolic acid or salts thereof.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to an antibacterial composition and an antibacterial agent.

Background Art

[0002] Diiodomethyl-p-tolylsulfone (hereinafter also referred to as "DMTS"), which is one of diiodomethane compounds, has been conventionally used as an antifungal agent. The antifungal performance of a conventional antifungal agent containing only DMTS (hereinafter also referred to as "fungicide (DMTS)") is sufficient.

[0003] However, the fungicide (DMTS) does not have a sufficient effect (hereinafter also referred to as "antibacterial effect") of suppressing the growth of bacteria (for example, Staphylococcus aureus, Bacillus subtilis, etc.). Therefore, the development of a composition containing DMTS and showing a high antibacterial effect is desired.

[0004] So far, various studies have been conducted to improve the antibacterial effect of DMTS (for example, Patent Document 1). Patent Document 1 discloses an antimicrobial agent composition containing DMTS and 1,2-dibromo-2,4-dicyanobutane.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, the antibacterial effect of the antimicrobial agent composition disclosed in Patent Document 1 against Gram-positive bacteria may not be sufficient. Furthermore, in order to improve the handleability, a composition containing DMTS is required to have water solubility.

[0007] An object to be solved by one embodiment of the present disclosure is to provide an antibacterial composition containing a diiodomethane compound that has water solubility and is superior in antibacterial effect against Gram-positive bacteria as compared with the case of using the diiodomethane compound alone. Another object to be solved by an embodiment of the present disclosure is to provide an antibacterial agent capable of improving the antibacterial effect against Gram-positive bacteria of a composition containing a diiodomethane compound and a cyclodextrin derivative.

Means for Solving the Problems

[0008] By adding a commercially available antibacterial agent to the composition containing DMTS, the antibacterial effect of the composition can be improved. However, considering the safety to the human body, it is preferable to use a component that is not a commercially available antibacterial agent. Therefore, the present inventors conducted various studies to improve the antibacterial effect of the composition containing the diiodomethane compound. As a result, although the reason is not clear, by adding a cyclodextrin derivative and a compound known to act on intercellular lipids to the diiodomethane compound, an antibacterial composition having water solubility and excellent antibacterial effect against Gram-positive bacteria was obtained, and the present invention was completed.

[0009] Specific means for solving the above problems include the following aspects. <1> A diiodomethane compound (A), A cyclodextrin derivative (B), A compound (C), containing The compound (C) contains at least one selected from the group consisting of pyrrolidones, organic acids, terpenes, ureas and urea derivatives, alcohols, esters, chelate compounds, antioxidants, surfactants, and thioglycolic acid or a salt thereof, an antibacterial composition. <2> The alcohols are propylene glycol, glycerin, or isopropanol, The terpenes are limonene, The pyrrolidones are 1-methyl-2-pyrrolidone, The organic acid is lactic acid, tartaric acid, succinic acid, or propionic acid, The chelate compound is calcium lignate, The antioxidant is tocopherol, The esters are isopropyl myristate, The surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol, The urea and urea derivatives are urea or 1,3-diphenylurea, The thioglycolic acid or its salt is calcium thioglycolate trihydrate, the antibacterial composition according to <1>. <3>The antibacterial composition according to <2>, wherein the compound (C) contains at least one selected from the group consisting of limonene, urea, propylene glycol, and polyoxyethylene polypropylene glycol. <4>The antibacterial composition according to any one of <1> to <3>, wherein the diiodomethane compound (A) contains diiodomethyl p-tolyl sulfone. <5>The antibacterial composition according to any one of <1> to <4>, wherein the cyclodextrin derivative (B) contains a β-cyclodextrin derivative (B1). <6>The antibacterial composition according to <5>, wherein the β-cyclodextrin derivative (B1) contains methyl-β-cyclodextrin. <7>An antibacterial composition containing a diiodomethane compound, a cyclodextrin derivative, and an antibacterial active agent. <8>containing at least one selected from the group consisting of 1-methyl-2-pyrrolidone, oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, propionic acid, (R)-(+)-limonene, L-menthol, urea, 1,3-diphenylurea, propylene glycol, isopropanol, sorbitan monooleate, calcium lignate salt, calcium thioglycolate trihydrate, and polyoxyethylene polyoxypropylene glycol, An antibacterial agent used in a composition containing a diiodomethane compound and a cyclodextrin derivative.

Advantages of the Invention

[0010] According to the present disclosure, there is provided an antibacterial composition having water solubility and excellent antibacterial effect against Gram-positive bacteria. According to the present disclosure, there is provided an antibacterial agent capable of improving the antibacterial effect of a composition containing a diiodomethane compound and a cyclodextrin derivative against Gram-positive bacteria.

Modes for Carrying Out the Invention

[0011] In the present disclosure, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. In the present disclosure, the amount of each component in the composition means the total amount of the plurality of substances present in the composition when there are a plurality of substances corresponding to each component in the composition, unless otherwise specified. In the numerical ranges described stepwise in the present disclosure, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in other stepwise descriptions. In the numerical ranges described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples. In the present disclosure, a combination of preferred embodiments is a more preferred embodiment. In the notation of the group (atomic group) in the present disclosure, the notation without indicating substitution and non-substitution includes both those having no substituent and those having a substituent.

[0012] (1) First Embodiment The antibacterial composition of the first embodiment of the present disclosure contains a diiodomethane compound (A), a cyclodextrin derivative (B), and a compound (C) (hereinafter also referred to as "antibacterial agent (C)"). The compound (C) includes at least one selected from the group consisting of pyrrolidones, organic acids, terpenes, ureas and urea derivatives, alcohols, esters, chelate compounds, antioxidants, surfactants, and thioglycolic acid or a salt thereof.

[0013] The "antibacterial composition" refers to a composition having an antibacterial effect. Specifically, it refers to a composition having a MIC value of Staphylococcus aureus of 31.3 ppm or less. The method for measuring the MIC value of Staphylococcus aureus is the same as the method described in the examples. The "diiodomethane compound (A)" refers to benzene having a diiodomethyl group and its derivatives (for example, α,α-diiodoacetylbenzene derivatives, α,α-diiodomethylsulfonylbenzene derivatives). The "cyclodextrin derivative" refers to a cyclodextrin-based compound containing cyclodextrin or its derivative, and includes cyclodextrin and cyclodextrin having a substituent. The "pyrrolidones" refer to organic compounds having a pyrrolidone skeleton. The "organic acids" refer to organic compounds having at least one carboxyl group and ionizing to produce hydrogen ions. The "terpenes" refer to organic compounds having a skeleton of isoprene represented by the chemical formula CH 2 =C(CH 3 )CH=CH 2 The "ureas and urea derivatives" refer to urea-based compounds containing urea or its derivatives, and include urea and urea having a substituent. The "alcohols" refer to compounds in which at least one hydrogen atom of a hydrocarbon having a linear, branched or cyclic structure is substituted with a hydroxy group. The "esters" refer to organic compounds obtained by a dehydration condensation reaction between an organic compound containing a hydroxyl group and an organic compound having a carboxy group. An "antioxidant" refers to an organic compound that contributes to a reaction that detoxifies by capturing reactive oxygen species (e.g., oxygen free radicals, hydroxyl radicals, superoxide anions, hydrogen peroxide, etc.).

[0014] Since the antibacterial composition of the first embodiment has the above configuration, it has water solubility and excellent antibacterial effect against Gram-positive bacteria. The Gram-positive bacteria may be Staphylococcus aureus.

[0015] The form of the antibacterial composition is not particularly limited, and examples include solutions (e.g., aqueous solutions or non-aqueous solutions), suspensions (i.e., slurry liquids), powders, pellets, and the like. The solution is obtained by dissolving the diiodomethane compound (A) in a solvent (D). Details of the solvent (D) will be described later.

[0016] (1.1) Diiodomethane compound (A) The antibacterial composition of the first embodiment contains a diiodomethane compound (A).

[0017] As the diiodomethane compound (A), known diiodomethane compounds can be used, but from the viewpoint of exhibiting a good antibacterial effect of the antibacterial composition, it preferably contains a compound (1) represented by the following general formula (1).

[0018]

Chemical formula

[0019] In general formula (1), R 1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, an alkylaminocarbonyl group having 2 to 7 carbon atoms, or a dialkylaminocarbonyl group having 3 to 13 carbon atoms, and R 2 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents 0 or 1. L1 represents a carbonyl group or a sulfonyl group.

[0020] R1 The alkyl group having 1 to 6 carbon atoms represented by may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. R 1 The number of carbon atoms of the alkyl group represented by is preferably 1 to 3, more preferably 1 to 2. R 1 Specific examples of the alkyl group having 1 to 6 carbon atoms represented by include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, cyclohexyl group and the like.

[0021] R 1 Specific examples of the acyl group having 1 to 7 carbon atoms represented by include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, pentanoyl group, pivaloyl group, hexanoyl group, heptanoyl group, benzoyl group and the like.

[0022] R 1 As the alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms represented by, an alkoxy group having 1 to 6 carbon atoms is preferable, an alkoxy group having 1 to 3 carbon atoms is more preferable, and an alkoxy group having 1 to 2 carbon atoms is still more preferable. The alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms may be a linear alkoxy group, a branched alkoxy group, or an alkoxy group having a cyclic structure, and is preferably a linear alkoxy group or a branched alkoxy group. Specific examples of the alkoxy group constituting the alkoxycarbonyl group having 2 to 7 carbon atoms include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, cyclobutoxy group, n-pentyloxy group, isopentyloxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropoxy group, cyclopentyloxy group, n-hexyloxy group, 4-methylpentyloxy group, 3-methylpentyloxy group, 2-methylpentyloxy group, 1-methylpentyloxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethylbutoxy group, 2,3-dimethylbutoxy group, 2-ethylbutoxy group, cyclohexyloxy group and the like.

[0023] R 1 The alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms represented by is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and still more preferably an alkyl group having 1 to 2 carbon atoms. The alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. Specific examples of the alkyl group constituting the alkylaminocarbonyl group having 2 to 7 carbon atoms or the dialkylaminocarbonyl group having 3 to 13 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, cyclohexyl group and the like.

[0024] R 1 The two alkyl groups constituting the dialkylaminocarbonyl group having 3 to 13 carbon atoms represented by may be the same or different. The two alkyl groups may be bonded to each other to form a cyclic structure.

[0025] R 1 is preferably a hydrogen atom or an alkoxycarbonyl group having 2 to 7 carbon atoms, and more preferably a hydrogen atom or an ethoxycarbonyl group.

[0026] R 2 The alkyl group having 1 to 6 carbon atoms represented by may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a linear alkyl group or a branched alkyl group. R 2 The number of carbon atoms of the alkyl group represented by is preferably 1 to 3, more preferably 1 to 2, and still more preferably 1. R 2Specific examples of the alkyl group having 1 to 6 carbon atoms represented by include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a cyclobutyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a cyclopentyl group, an n-hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a cyclohexyl group, and the like.

[0027] R 2 Specific examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0028] R 2 The substitution position of is not particularly limited. The substitution position of R 2 may be an ortho position, a meta position, or a para position based on the carbon atom to which L1 is bonded in the benzene ring of the general formula (1), and is preferably a para position.

[0029] R 2 is preferably a methyl group or an ethyl group, and more preferably a methyl group.

[0030] n represents 0 or 1, and is preferably 1.

[0031] L1 represents a carbonyl group or a sulfonyl group.

[0032] Examples of the diiodomethane compound (A) include diiodomethyl-p-toluenesulfone (hereinafter also referred to as "DMTS"), diiodomethyl-o-toluenesulfone, diiodomethyl-m-toluenesulfone, diiodomethyl-p-chlorophenylsulfone, diiodomethyl-p-bromophenylsulfone, diiodomethyl-p-ethylphenylsulfone, diiodomethyl-p-propylphenylsulfone, diiodomethyl phenyl ketone, diiodomethyl(4-methylphenyl)ketone, diiodomethyl(4-chlorophenyl)ketone, methyl 2,2-diiodo-3-oxo-3-phenylpropionate, and the like. Among them, from the viewpoint of expressing a good antibacterial effect of the antibacterial composition, the diiodomethane compound (A) preferably contains at least one selected from the group consisting of diiodomethyl-p-toluenesulfone, diiodomethyl-o-toluenesulfone, diiodomethyl-m-toluenesulfone, and diiodomethyl-p-chlorophenylsulfone, and more preferably contains diiodomethyl-p-toluenesulfone.

[0033] The diiodomethane compound (A) may be a commercially available product. Examples of commercially available products include "Yotole (registered trademark) DP95" (manufactured by Mitsui Chemicals, Inc., main component: DMTS), "Yotole (registered trademark) DP-CD" (manufactured by Mitsui Chemicals, Inc., main components: DMTS and methyl-β-cyclodextrin (hereinafter also referred to as "MβCD")), and the like.

[0034] (1.1.1) Content The content of the diiodomethane compound (A) is not particularly limited and is appropriately selected according to the form of the antibacterial composition. When the form of the antibacterial composition is a solution, the content of the diiodomethane compound (A) is preferably 0.01% by mass to 10% by mass, more preferably 0.1% by mass to 5.0% by mass, still more preferably 1.0% by mass to 4.0% by mass, and particularly preferably 1.5% by mass to 3.5% by mass with respect to the total amount of the antibacterial composition. When the form of the antibacterial composition is a powder, the content of the diiodomethane compound (A) is preferably 0.01% by mass to 99% by mass, more preferably 0.1% by mass to 40% by mass, and still more preferably 5% by mass to 35% by mass with respect to the total amount of the antibacterial composition. In the present disclosure, the content of the diiodomethane compound (A) is regarded as the same as the addition ratio (mixing ratio) of the diiodomethane compound (A).

[0035] (1.2) Cyclodextrin derivative (B) The antibacterial composition of the first embodiment contains a cyclodextrin derivative (B).

[0036] When the antibacterial composition further contains a cyclodextrin derivative (B), an inclusion compound is likely to be formed. The inclusion compound may include a diiodomethane compound (A) as a guest compound and a cyclodextrin derivative (B) as a host compound. The cyclodextrin derivative (B) has high solubility in water. Therefore, even when the diiodomethane compound (A) has low solubility in water (for example, DMTS), the inclusion compound has high solubility in water. As a result, the antibacterial composition can be used in the form of a solution. Therefore, the handleability of the antibacterial composition is more excellent.

[0037] Examples of the substituent in the cyclodextrin derivative (B) include an alkyl group and a hydroxyalkyl group. The number of carbon atoms in the alkyl group and the hydroxyalkyl group is preferably 1 to 10, more preferably 1 to 3, and still more preferably 1.

[0038] The cyclodextrin derivative (B) may be any of an α-cyclodextrin derivative, a β-cyclodextrin derivative (B1), and a γ-cyclodextrin derivative, or a mixture thereof. Specifically, examples of the cyclodextrin derivative (B) include methyl-β-cyclodextrin, hydroxypropyl-β-cyclodextrin, methyl-γ-cyclodextrin, methyl-α-cyclodextrin, and the like. Among them, from the viewpoint of making it easier to form an inclusion compound, etc., the cyclodextrin derivative (B) preferably contains a β-cyclodextrin derivative (B1) (that is, a β-cyclodextrin-based compound containing β-cyclodextrin or a derivative thereof). From the viewpoint of improving the solubility of the diiodomethane compound (A) in an aqueous solution, etc., the β-cyclodextrin derivative (B1) preferably contains methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin, and more preferably contains methyl-β-cyclodextrin.

[0039] The β-cyclodextrin derivative may be a commercially available product. Examples of commercially available products include "CAVASOL W7 M" (methyl-β-cyclodextrin, manufactured by Cyclochem), "CAVASOL W7 HP" (hydroxypropyl-β-cyclodextrin, manufactured by Cyclochem), "Chemically Modified Cyclodextrin Methyl-β-CD" (manufactured by Shimizu Port Sugar Refining Co., Ltd.), "Chemically Modified Cyclodextrin HP-β-CD" (manufactured by Shimizu Port Sugar Refining Co., Ltd.), "Celdex HP-β-CD" (manufactured by Nippon Food Chemical Co., Ltd.), etc.

[0040] (1.2.1) Content The content of the cyclodextrin derivative (B) is not particularly limited and is appropriately selected according to the form of the antibacterial composition. When the form of the antibacterial composition is a solution or a powder, the content of the cyclodextrin derivative (B) is preferably 300% by mass to 3600% by mass, more preferably 600% by mass to 2700% by mass, and still more preferably 900% by mass to 2100% by mass, based on the total mass of the diiodomethane compound (A), from the viewpoint of improving the solubility of the antibacterial composition in water, etc. When the form of the antibacterial composition is a solution, the content of the cyclodextrin derivative (B) is preferably 5% by mass to 80% by mass, more preferably 20% by mass to 60% by mass, and still more preferably 30% by mass to 40% by mass, based on the total amount of the antibacterial composition. When the form of the antibacterial composition is powder, the content of the cyclodextrin derivative (B) is preferably 10% by mass to 99% by mass, more preferably 50% by mass to 98% by mass, and still more preferably 80% by mass to 95% by mass with respect to the total amount of the antibacterial composition. In the present disclosure, the content of the cyclodextrin derivative (B) is regarded as the same as the addition ratio (blending ratio) of the cyclodextrin derivative (B).

[0041] (1.3) Compound (C) The antibacterial composition of the first embodiment contains an antibacterial agent (C).

[0042] The antibacterial agent (C) of the first embodiment contains at least one selected from the group consisting of pyrrolidones, organic acids, terpenes, ureas and urea derivatives, alcohols, esters, chelate compounds, antioxidants, surfactants, and thioglycolic acid or a salt thereof.

[0043] Examples of pyrrolidones include 1-methyl-2-pyrrolidone and the like. Examples of organic acids include fatty acids or salts thereof (e.g., oleic acid, decanoic acid, isostearic acid, stearic acid, lauric acid, myristic acid, palmitic acid, linoleic acid, sodium oleate, sodium decanoate, sodium isostearate, sodium stearate, sodium laurate, sodium myristate, sodium palmitate, sodium linoleate, etc.), α-hydroxy acids or salts thereof (e.g., lactic acid, malic acid, glycolic acid, citric acid, sodium lactate, etc.), carboxylic acids (e.g., tartaric acid, succinic acid, propionic acid, salicylic acid, etc.). Examples of terpenes include limonene (e.g., (R)-(+)-limonene, etc.), menthol (e.g., L-menthol, etc.), camphor, geraniol, etc. Examples of urea derivatives include 1,3-diphenylurea, N,N'-dimethylpropyleneurea (DMPU), etc. Examples of the alcohols include polyhydric alcohols (e.g., propylene glycol, glycerin, polyethylene glycol, 1,3-butylene glycol, dipropylene glycol, etc.), aliphatic alcohols (e.g., oleyl alcohol, isostearyl alcohol, octyldodecanol, lauryl alcohol, myristyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, cetyl alcohol, cetanol, benzyl alcohol, etc.), and lower alcohols (e.g., isopropanol, ethanol, etc.). Examples of the esters include isopropyl myristate, isopropyl palmitate, diisopropyl adipate, methyl laurate, diethyl sebacate, diisopropyl sebacate, diisobutyl adipate, dimethyl succinate, dibutyl phthalate, etc. Examples of the chelate compounds include calcium lignate, ethylenediaminetetraacetic acid (EDTA), etc. Examples of the antioxidants include tocopherol (e.g., (±)-α-tocopherol, etc.), ascorbic acid, dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), etc. Examples of the surfactants include sorbitan monooleate, polyoxyethylene (POE) polyoxypropylene glycol, glyceryl monostearate, glyceryl monooleate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitol tetra-stearate, polyoxyethylene sorbitol tetraoleate, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyethylene glycol monostearate, polyethylene glycol monooleate, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, N-acylglutamate, N-acylglycine, N-acylsarcosinate, etc. Examples of the thioglycolate include calcium thioglycolate trihydrate and the like.

[0044] In the antibacterial active agent (C), the pyrrolidones are 1-methyl-2-pyrrolidone, the organic acids are oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, or propionic acid, the terpenes are limonene or menthol, the urea and urea derivatives are urea or 1,3-diphenylurea, the alcohols are propylene glycol, glycerin, or isopropanol, the esters are isopropyl myristate, the chelate compound is calcium lignate, the antioxidant is tocopherol, the surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol, and the thioglycolic acid or its salt is preferably calcium thioglycolate trihydrate. In other words, the antibacterial active agent (C) is preferably at least one selected from the group consisting of 1-methyl-2-pyrrolidone, oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, propionic acid, limonene, menthol, urea, 1,3-diphenylurea, propylene glycol, glycerin, isopropanol, isopropyl myristate, calcium lignate, tocopherol, sorbitan monooleate, polyoxyethylene polyoxypropylene glycol, and calcium thioglycolate trihydrate. Thereby, the antibacterial effect of the antibacterial composition against Gram-positive bacteria is more excellent.

[0045] The compound (C) preferably contains at least one selected from the group consisting of limonene, urea, propylene glycol, and polyoxyethylene polypropylene glycol. Thereby, the antibacterial effect of the antibacterial composition against Gram-positive bacteria is further excellent.

[0046] (1.3.1) Content The content of the antibacterial active agent (C) is not particularly limited and is appropriately selected according to the form of the antibacterial composition. When the form of the antibacterial composition is a solution or a powder, the content of the antibacterial agent (C) is preferably 0.1% by mass to 200% by mass, more preferably 1% by mass to 30% by mass, still more preferably 5% by mass to 15% by mass, based on the total mass of the diiodomethane compound (A), from the viewpoint of improving the solubility of the antibacterial composition in water and the like. When the form of the antibacterial composition is a solution, the content of the antibacterial agent (C) is preferably 0.003% by mass to 6% by mass, more preferably 0.03% by mass to 0.9% by mass, still more preferably 0.15% by mass to 0.45% by mass, based on the total amount of the antibacterial composition. When the form of the antibacterial composition is a powder, the content of the antibacterial agent (C) is preferably 0.008% by mass to 16% by mass, more preferably 0.08% by mass to 2.4% by mass, still more preferably 0.4% by mass to 1.2% by mass, based on the total amount of the antibacterial composition. In the present disclosure, the content of the antibacterial agent (C) is regarded as the same as the addition ratio (blending ratio) of the antibacterial agent (C).

[0047] (1.4) Solvent The antibacterial composition of the first embodiment may further contain a solvent (D) in addition to the diiodomethane compound (A), the cyclodextrin derivative (B), and the antibacterial agent (C), or may not contain the solvent (D). When the antibacterial composition contains the solvent (D), the form of the antibacterial composition can be a solution. Therefore, the handleability of the antibacterial composition is superior to the case where the form of the antibacterial composition is a powder.

[0048] Examples of the solvent (D) include water-soluble solvents and water-insoluble solvents. The water-soluble solvent may be any solvent containing water, and examples thereof include water (e.g., purified water, ion-exchanged water), physiological saline, and the like. The water-insoluble solvent may be any solvent not containing water, and examples thereof include organic solvents. Examples of the organic solvent include sulfur atom-containing solvents (e.g., dimethyl sulfoxide, etc.), monohydric alcohols (e.g., ethanol, isopropanol, benzyl alcohol, etc.), glycol-based solvents (e.g., ethylene glycol, diethylene glycol, polyethylene glycol, etc.) and their derivatives, glycerin-based solvents (e.g., glycerin, diglycerin, etc.) and their derivatives, cyclic organic solvents (e.g., N-methylpyrrolidone, N-ethylpyrrolidone, etc.), ester-based solvents (e.g., phthalic acid esters, adipic acid esters, sebacic acid esters, etc.), ketone-based solvents (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), aromatic solvents (e.g., methylnaphthalene, phenylxylylethane, alkylbenzenes, etc.), aliphatic hydrocarbon solvents (e.g., normal paraffin, isoparaffin, etc.). These solvents may be used alone or in combination of two or more.

[0049] (1.4.1) Content The content of the solvent (D) is not particularly limited and is appropriately selected according to the use of the antibacterial composition and the like. When the antibacterial composition further contains the solvent (D), the content of the solvent (D) is preferably 30% by mass to 99% by mass, more preferably 50% by mass to 99% by mass, and still more preferably 50% by mass to 70% by mass based on the total amount of the antibacterial composition. In the present disclosure, the content of the solvent (D) is regarded as the same as the addition ratio (blending ratio) of the solvent (D).

[0050] (1.5) Other Components The antibacterial composition of the first embodiment may further contain other components (E) as needed, or may not contain other components (E), in addition to the diiodomethane compound (A), the cyclodextrin derivative (B), and the antibacterial agent (C). The other components (E) may be known components. For example, pH adjusters, defoaming agents, rust preventives, viscosity adjusters (e.g., thickeners), light stabilizers, ultraviolet absorbers, accelerators, adhesion promoters, fragrances, scale inhibitors, antistatic agents, resin binders, softening agents, antibacterial components, antiviral agents, other antifungal agents, etc. may be mentioned. These other components may be blended alone or in combination of two or more.

[0051] (1.6) Target bacteria The bacteria against which the antibacterial composition of the first embodiment exhibits an antibacterial effect are Gram-positive bacteria. Gram-positive bacteria include Staphylococcus aureus and Bacillus subtilis. The antibacterial composition of the first embodiment exhibits an antibacterial effect against Gram-negative bacteria as shown in the following examples. Gram-negative bacteria include Escherichia coli.

[0052] (1.7) Uses of the antibacterial composition The antibacterial composition of the first embodiment can be used for various purposes. As uses for the antibacterial composition, for example, it includes all members and products used as various industrial products and daily necessities, etc. Specifically, as the above uses, for example, in the agricultural field (e.g., agricultural chemicals, etc.), forestry field (e.g., wood preservatives, etc.), fishery field (e.g., floats, fishing gear, and aquariums, etc.), livestock field (e.g., feed, feeding troughs, and calf jackets, etc.), construction field (e.g., interior building materials such as wallpapers, wall boards, wall materials, and floor materials, paints, adhesives, filters, tiles, cement, concrete, anti-termite agents and insect repellents for building materials, etc., and materials such as wood, etc.), food field (e.g., food preservatives, etc.), beverage / tobacco / feed field (e.g., water and tobacco, etc.), fiber field (e.g., clothing and futons, etc.), pulp / paper / paper processed products field (e.g., packaging materials such as wrapping paper, etc.), chemical industry field (e.g., surface treatment agents such as metal working fluids, detergents, cooling water, plating solutions, etc., cutting fluids for plastics or glass (e.g., lens processing fluid), inks, printing toners, pharmaceuticals, cosmetics, toiletries, sanitary products, bactericidal disinfectants, deodorants, preservatives, and detergents, etc.), plastic products field (e.g., resin moldings, films, and synthetic leather (e.g., polyurethane-based synthetic leather), etc.), rubber products field, tanned leather / leather products / fur field (e.g., leather, etc.), ceramics / stone products field (e.g., tableware and other ceramics, etc.), electrical and mechanical appliances field (e.g., household electrical appliances such as refrigerators and air conditioners and their components, etc.), transportation machinery appliances field (e.g., automobiles and ships for logistics, etc.), precision machinery appliances field (e.g., high-tech equipment and optical equipment, etc.), other product fields (e.g., sports goods, school supplies, ink for writing instruments, toys, miscellaneous goods made of plastics, etc., and household goods, etc.), and medical / welfare service field (e.g., members and products used in hospitals, nursing homes, and public facilities, etc.), etc., it can be used for the members and products respectively exemplified in each field.

[0053] Among them, as the uses of the antibacterial composition, interior building materials, paints, inks, printing toners, wallpapers, adhesives, metalworking fluids, surface treatment agents, cutting fluids for plastics or glass (e.g., lens processing fluids), molded articles (e.g., films, sheets, and plastic products (e.g., resin moldings and synthetic leathers (e.g., polyurethane-based synthetic leathers), etc.)), fibers (clothes, futons, etc.), ceramics (tableware, etc.), paper and pulp products, detergents, deodorants, preservatives, and rubber product fields are suitable.

[0054] That is, by processing the members and products, etc. in the fields exemplified above so as to contain the antibacterial composition of the first embodiment, it becomes possible to impart an antibacterial effect to the members and products, etc.

[0055] (1.8) Formulation of the antibacterial composition The antibacterial composition of the first embodiment may be used for various applications after formulating the antibacterial composition. By formulating and using the antibacterial composition, the antibacterial composition of the first embodiment may be more easily applicable to the fields, members, products, etc. as described above. The dosage form obtained by formulation is not particularly limited, and various dosage forms such as aqueous systems, powder systems, and solvent systems (e.g., oil agents, emulsions, solubilized preparations, wettable powders, flowables (aqueous suspensions, aqueous emulsions, etc.), microcapsule agents, powders, tablets, aerosol agents, and carbon dioxide gas preparations, etc.) are applicable. The antibacterial composition of the first embodiment can be formulated together with optional components generally used in formulation.

[0056] (2) Second embodiment The antibacterial composition according to the second embodiment of the present disclosure contains a diiodomethane compound, a cyclodextrin derivative, and an antibacterial activator.

[0057] The diiodomethane compound is the same as those exemplified as the diiodomethane compound (A) of the first embodiment. The cyclodextrin derivative is the same as those exemplified as the cyclodextrin derivative (B) of the first embodiment.

[0058] The "antibacterial active agent" is an agent that exhibits an antibacterial effect in an antibacterial composition and does not include commercially available antibacterial agents at the time of this application.

[0059] Since the antibacterial composition of the second embodiment has the above configuration, it has water solubility and is excellent in antibacterial effect against Gram-positive bacteria. The Gram-positive bacteria may be Staphylococcus aureus.

[0060] The form of the antibacterial composition is not particularly limited, and examples include solutions (e.g., aqueous solutions or non-aqueous solutions), suspensions (i.e., slurry liquids), powders, pellets, and the like.

[0061] (2.1) Antibacterial active agent In addition to those similar to those exemplified as the antibacterial active agent (C) of the first embodiment, the antibacterial active agent of the second embodiment includes amines (such as monoethanolamine, diethanolamine, triethanolamine, etc.), AZONEs (such as AZONE), enamine derivatives, polyamines, polycations (such as polyarginine, polyethyleneimine, etc.), chitosans (such as chitosan), hydrocarbon oils (such as liquid paraffin), silicone oils (such as dimethyl silicone oil, methylphenyl silicone oil, methylhydrogen silicone oil, etc.), dendrimers, membrane-permeable peptides, and the like.

[0062] (2.2) Solvent The antibacterial composition of the second embodiment may further contain a solvent or may not contain a solvent in addition to the diiodomethane compound, cyclodextrin derivative, and antibacterial active agent. The solvent is the same as that exemplified as the solvent (D) of the first embodiment.

[0063] (2.3) Other components The antibacterial composition of the second embodiment may further contain other components or may not contain other components as necessary in addition to the diiodomethane compound, cyclodextrin derivative, and antibacterial active agent. The other components are the same as those exemplified as the other components (E) of the first embodiment.

[0064] (2.4) Target bacteria The bacteria against which the antibacterial composition of the second embodiment exhibits an antibacterial effect are Gram-positive bacteria. Gram-positive bacteria include Staphylococcus aureus and Bacillus subtilis. The antibacterial composition of the second embodiment also exhibits an antibacterial effect against Gram-negative bacteria as shown in the following examples. Gram-negative bacteria include Escherichia coli.

[0065] (2.5) Use of the antibacterial composition The use of the antibacterial composition of the second embodiment is not particularly limited, and examples thereof include the same ones as those exemplified as the use of the antibacterial composition of the first embodiment.

[0066] (2.6) Formulation of the antibacterial composition The antibacterial composition of the second embodiment may be used for various purposes after formulating the antibacterial composition. Examples of the formulation of the antibacterial composition of the second embodiment include the same ones as those exemplified as the formulation of the antibacterial composition of the first embodiment.

[0067] (3) Antibacterial agent The antibacterial agent of the present disclosure includes at least one selected from the group consisting of 1-methyl-2-pyrrolidone, oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, propionic acid, (R)-(+)-limonene, L-menthol, urea, 1,3-diphenylurea, propylene glycol, isopropanol, sorbitan monooleate, calcium lignate, calcium thioglycolate trihydrate, and polyoxyethylene polyoxypropylene glycol. The antibacterial agent of the present disclosure is used in a composition containing a diiodomethane compound and a cyclodextrin derivative.

[0068] Since the antibacterial agent of the present disclosure has the above configuration, it can improve the antibacterial effect against Gram-positive bacteria in a composition containing a diiodomethane compound and a cyclodextrin derivative. The Gram-positive bacteria may be Staphylococcus aureus.

[0069] Among them, the antibacterial agent of the present disclosure preferably contains at least one selected from the group consisting of (R)-(+)-limonene, urea, propylene glycol, and polyoxyethylene polyoxypropylene glycol. Thereby, the antibacterial agent of the present disclosure can further improve the antibacterial effect against Gram-positive bacteria.

Examples

[0070] Hereinafter, the present disclosure will be described in more detail with reference to examples. However, the present disclosure is not limited to the following examples as long as the gist thereof is not exceeded. Unless otherwise specified, "parts" are based on mass.

[0071] [1] Raw materials The products used in the examples and comparative examples are as follows.

[0072] [1.1] Diiodomethane compound (A) · DMTS: "Yotole (registered trademark) DP95" manufactured by Mitsui Chemicals, Inc. (component: diiodomethyl-p-toluenesulfone, form: powder) was used.

[0073] [1.2] Cyclodextrin derivative (B) · MβCD: "CAVASOL (registered trademark) W7 M" manufactured by Cyclochem Co., Ltd. (component: methyl-β-cyclodextrin, form: powder) was used. · βCD: β-Cyclodextrin

[0074] [1.3] Antibacterial agent (C) and antibacterial agent (C1) · 1-Methyl-2-pyrrolidone · Oleic acid · Decanoic acid · Lactic acid · Tartaric acid · Succinic acid · Propionic acid · R+ limonene: (R)-(+)-Limonene · L-menthol: l-Menthol · Urea · 1,3-Diphenylurea · Propylene glycol · Glycerin · Isopropanol · Isopropyl myristate · Sorbitan monooleate · (±)-α-Tocopherol: (+ / -)-α-Tocopherol · Calcium lignate · Calcium thioglycolate trihydrate: Calcium thioglycolate trihydrate · POE polyoxypropylene glycol: Polyoxyethylene polyoxypropylene glycol

[0075] [1.4] Solvent (D) · DMSO: Dimethyl sulfoxide · Water: Purified water

[0076] [1.5] Monoiodo compound (X) · IPBC: 3-Iodo-2-propynyl butylcarbamate

[0077] [2] Examples and comparative examples of antibacterial compositions [2.1] Examples 1-1 to 1-20 and comparative examples 1-1 to 1-42 The diiodomethane compound (A), cyclodextrin derivative (B), antibacterial agent (C), and solvent (D) shown in Tables 1 to 3 were mixed at the ratios shown in Tables 1 to 3 to obtain an antibacterial composition.

[0078] [2.2] Evaluation of antibacterial compositions The antibacterial effect, antifungal effect, and water solubility of the antibacterial composition were evaluated as follows. The evaluation results are shown in Tables 1 to 3.

[0079] [2.2.1] Evaluation of antibacterial effect The antibacterial effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0080] [2.2.1.1] Medium In the antibacterial test, the following LB (Lysogeny Broth) medium was used. The LB medium was prepared by dissolving 25 g of "Difco LB Broth Miller (Luria - Bertani)" (manufactured by Becton Dickinson and Company) in 1000 mL of distilled water.

[0081] [2.2.1.2] Pre - culture In the antibacterial test, the following bacterial species (a1), (a2), and (a3) were used. Bacterial species (a1), (a2), and (a3) are test bacterial species cultured at 35°C for 24 hours using an LB medium autoclaved at 121°C for 20 minutes.

[0082] Bacterial species (a1): Staphylococcus aureus (NBRC 12732, distributing agency: National Institute of Technology and Evaluation, Staphylococcus aureus) Bacterial species (a2): Bacillus subtilis (NBRC 13719, distributing agency: National Institute of Technology and Evaluation, Bacillus subtilis) Bacterial species (a3): Escherichia coli (NBRC 3972, distributing agency: National Institute of Technology and Evaluation, Escherichia coli)

[0083] [2.2.1.3] Sample preparation The antibacterial compositions shown in Tables 1 - 3 were added to an LB medium autoclaved at 121°C for 20 minutes, and a 12 - step two - fold dilution series with a maximum concentration of the active ingredient of 1000 ppm was prepared on a multi - well plate. Thereby, an antibacterial composition - containing medium was obtained. The "maximum concentration of the active ingredient" in the MIC test method (bacteria) in Table 1 indicates the ratio (mass %) of the mass of the antibacterial agent (C) in the antibacterial composition - containing medium calculated from the amount of the antibacterial agent (C) blended with respect to the total mass of the antibacterial composition - containing medium. The "maximum concentration of the active ingredient" in the MIC test method (bacteria) in Tables 2 and 3 indicates the ratio (mass %) of the mass of (A) in the antibacterial composition - containing medium calculated from the amount of the diiodomethane compound (A) blended with respect to the total mass of the antibacterial composition - containing medium.

[0084] [2.2.1.4] Bacterial suspension preparation The test bacterial strain was suspended in LB medium sterilized by autoclaving at 121°C for 20 minutes, and the suspension was prepared so that the O.D. (Optical Density) was 1.0 - 2.0. Thus, a bacterial suspension was obtained.

[0085] [2.2.1.5] MIC measurement (bacteria) 2 μL of the bacterial suspension of the bacterial strains listed in Tables 1 - 3 was inoculated into each 100 μL of the dilution series of the medium containing the antibacterial composition, and cultured at 35°C for 18 - 24 hours. The growth of bacteria was visually confirmed, and the minimum dilution concentration without bacterial growth was taken as the MIC value. When the medium containing the antibacterial composition was clear, it was judged that there was no bacterial growth. The lower the MIC value, the better the antibacterial effect. The acceptable range of the MIC value of Staphylococcus aureus is 31.3 ppm or less. The MIC values listed in Table 1 refer to the MIC values of antibacterial agent (C), and the MIC values listed in Tables 2 and 3 refer to the MIC values of diiodomethane compound (DMTS).

[0086] The MIC test (bacteria) was carried out 3 times in total. If the MIC values of the 3 MIC tests (bacteria) are different and some are outside the measurement range and the values cannot be specified, they are described in Tables 1 - 3 in the form of ">1000". ">1000" indicates that the minimum value of the MIC value exceeded 1000 ppm.

[0087] [2.2.2] Evaluation of antifungal effect The antifungal effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0088] [2.2.2.1] Medium and surfactant solution In the MIC test (fungus), the following PDA (Potato Dextrose Agar) medium, PDB (Potato Dextrose Broth) medium, and surfactant solution were used. The PDA medium is prepared by dissolving 39 g of "Difco Potato Dextrose Agar" (manufactured by Becton, Dickinson and Company) in 1000 mL of distilled water, and adding 1 mL of chloramphenicol (reagent grade, manufactured by Fujifilm Wako Pure Chemical Corporation) diluted to 50 mg / mL with ethanol. The PDB medium is prepared by dissolving 24 g of "Difco Potato Dextrose Broth" (manufactured by Becton, Dickinson and Company) in 1000 mL of distilled water, and adding 1 mL of chloramphenicol (reagent grade, manufactured by Fujifilm Wako Pure Chemical Corporation) diluted to 50 mg / mL with ethanol. The surfactant solution is prepared by dissolving 8.5 g of "sodium chloride" (reagent grade, manufactured by Fujifilm Wako Pure Chemical Corporation), 0.5 mL of "polyoxyethylene (20) sorbitan monooleate" (for molecular biology, manufactured by Fujifilm Wako Pure Chemical Corporation) in 1000 mL of distilled water.

[0089] [2.2.2.2] Pre-culture In the MIC test (fungus), the following fungal species (b1) were used. The fungal species (b1) are test fungal species cultured at 25°C for 7 days or more using PDA medium autoclaved at 121°C for 20 minutes.

[0090] Fungal species (b1): Aspergillus niger (NBRC 105649, distributing agency: National Institute of Technology and Evaluation, black koji mold)

[0091] [2.2.2.3] Sample preparation The antibacterial compositions shown in Tables 1 to 3 were added to PDB medium autoclaved at 121°C for 20 minutes, and an 11-step two-fold dilution series with a maximum concentration of the active ingredient of 100 ppm was prepared. Thereby, a medium containing the antibacterial composition was obtained. In Table 1, the "maximum concentration of active ingredient" in the MIC test method (fungus) indicates the percentage by mass (% by mass) of the mass of the antibacterial agent (C) in the antibacterial composition-containing medium calculated from the amount of the antibacterial agent (C) compounded with respect to the total mass of the antibacterial composition-containing medium. In Tables 2 and 3, the "maximum concentration of active ingredient" in the MIC test method (fungus) indicates the percentage by mass (% by mass) of the mass of (A) in the antibacterial composition-containing medium calculated from the amount of the diiodomethane compound (A) compounded with respect to the total mass of the antibacterial composition-containing medium.

[0092] [2.2.2.4] Fungus solution preparation The test fungus species was suspended in a surfactant solution autoclaved at 121 °C for 20 minutes, and using a hemocytometer, the spore count was adjusted to be 1×10 5 / mL to 100×10 5 / mL. Thus, a fungus solution was obtained.

[0093] [2.2.2.5] MIC measurement (fungus) 100 μL of the fungus solution of the fungus species was inoculated into each 2 mL of the dilution series of the prepared antibacterial composition-containing medium, and cultured at 25 °C for 7 days. The growth of the fungus was visually confirmed, and the minimum dilution concentration without the growth of the fungus was taken as the MIC value. When no lumps of the fungus mycelium were visually confirmed in the antibacterial composition-containing medium, it was judged that there was no growth of the fungus. The lower the MIC value, the better the antifungal effect is indicated.

[0094] The MIC test (fungus) was carried out 2 times in total. When the MIC values measured in the two MIC tests (fungus) were different, the two MIC values were described in Tables 1 to 3.

[0095] [2.2.3] Evaluation test of water solubility The water solubility of the antibacterial composition was evaluated by the following evaluation test.

[0096] [2.2.3.1] Evaluation test A water-soluble evaluation antibacterial composition was obtained in the same manner as in Example 1-1 and the like, except that the solvent (D) was not added. The water-soluble evaluation antibacterial composition contained the iodomethane compound (A), cyclodextrin derivative (B), and antibacterial agent (C) shown in Tables 1 to 3 in the proportions shown in Tables 1 to 3.

[0097] 900 mg of the water-soluble evaluation antibacterial composition was charged into 29.1 g of distilled water and stirred with a stirrer chip for 5 minutes. After stopping the stirring, it was observed visually to see if any precipitate remained.

[0098] Based on the observation results, the water solubility of the antibacterial composition was evaluated according to the following evaluation criteria. An acceptable evaluation result for the water solubility of the antibacterial composition is "A".

[0099] [2.2.3.2] Evaluation Criteria "A": No precipitate can be confirmed visually, and it is a uniform aqueous solution. "B": Precipitation of undissolved matter can be confirmed visually.

[0100] [2.2.4] Evaluation Results [Table 1]

[0101] [Table 2]

[0102] [Table 3]

[0103] In Tables 1 to 3, "(A)" indicates the diiodomethane compound (A). "(B)" indicates the cyclodextrin derivative (B). "(C)" indicates the antibacterial agent (C). "(D)" indicates the solvent (D). "S.aureus" indicates Staphylococcus aureus. "B.subtilis" indicates Bacillus subtilis. "E.coli" indicates Escherichia coli. "A.niger" indicates Aspergillus niger.

[0104] In Table 1, the "*" in the MIC values of Staphylococcus aureus in Comparative Examples 1-11 indicates that the evaluation was not possible because turbidity of the liquid was observed due to precipitation of the antibacterial agent in the liquid medium of the well plate after antibacterial evaluation. From the measurement results of the MIC values of Staphylococcus aureus in Tables 1 to 3 (particularly Comparative Examples 1-32), it was clear that the MIC values of Staphylococcus aureus in Comparative Examples 1-11 were not 31.3 ppm or less.

[0105] In Comparative Examples 1-1 to 1-42, the antibacterial composition did not contain the diiodomethane compound (A), the cyclodextrin derivative (B), and the antibacterial agent (C). Therefore, the evaluation of water solubility in Comparative Examples 1-1 to 1-42 was "B". The MIC values of Staphylococcus aureus in Comparative Examples 1-1 to 1-32, 1-35, 1-39 to 1-42 were more than 31.3 ppm. From these results, it was found that the antibacterial compositions in Comparative Examples 1-1 to 1-42 were not "antibacterial compositions having water solubility and excellent antibacterial effects against Gram-positive bacteria".

[0106] In Examples 1-1 to 1-20, the antibacterial composition contained the diiodomethane compound (A), the cyclodextrin derivative (B), and the antibacterial agent (C). Therefore, the MIC values of Staphylococcus aureus in Examples 1-1 to 1-20 were 31.3 ppm or less. The evaluation of water solubility in Examples 1-1 to 1-20 was "A". From these results, it was found that the antibacterial compositions in Examples 1-1 to 1-20 were "antibacterial compositions having water solubility and excellent antibacterial effects against Gram-positive bacteria".

[0107] [3] Examples and Comparative Examples of Antibacterial Agents [3.1] Examples 2-1 to 2-17 The antibacterial agent (C1) shown in Tables 4 to 6 was prepared.

[0108] [3.2] Evaluation of Antibacterial Effects of Antibacterial Agents The iodoform compound (A), cyclodextrin derivative (B), antibacterial agent (C1), solvent (D) and monoiodomethane compound (X) shown in Tables 4 to 6 were mixed at the ratios shown in Tables 4 to 6 to obtain a composition for evaluation.

[0109] The antibacterial effect of the composition for evaluation was evaluated by the MIC (Minimum Inhibitory Concentration) test method. Specifically, in the same manner as described in "[2.2.1 Evaluation of antibacterial effect]" above, the MIC value of the composition for evaluation was determined. The measurement results are shown in Tables 4 to 6. The MIC values described in Tables 4 and 5 refer to the MIC values of the iodoform compound (DMTS), and the MIC values described in Table 6 refer to the MIC values of the monoiodomethane compound (IPBC).

[0110] [3.3] Evaluation results

Table 4

[0111]

Table 5

[0112]

Table 6

[0113] In Tables 4 to 6, "(C1)" indicates the antibacterial agent (C1). "(A)" indicates the iodoform compound (A). "(B)" indicates the cyclodextrin derivative (B). "(D)" indicates the solvent (D). "(X)" indicates the monoiodomethane compound (X). "S. aureus" indicates Staphylococcus aureus.

[0114] As shown in Tables 4 and 5, the MIC value of Staphylococcus aureus for the composition containing three components (antibacterial agent (C1), DMTS, and MβCD) was lower than that of the composition containing two components (antibacterial agent (C1) and DMTS). That is, it was found that the antibacterial effect can be dramatically improved by adding the antibacterial agent (C1) to the composition containing DMTS and MβCD. The antibacterial agent (C1) is a compound that is usually used as a transdermal absorption enhancer. As a result, it was found that the antibacterial agent (C1), which is used as a transdermal absorption enhancer, is an "antibacterial agent that can improve the antibacterial effect against Gram-positive bacteria of a composition containing a diiodomethane compound and a cyclodextrin derivative".

[0115] As shown in Table 6, the MIC value of Staphylococcus aureus for the composition containing three components (antibacterial agent (C1), IPBC, and βCD) was equivalent to that of the composition containing two components (antibacterial agent (C1) and IPBC). That is, it was found that even if the antibacterial agent (C1) is added to the composition containing IPBC and βCD, the antibacterial effect against Gram-positive bacteria cannot be improved. From these results, it was found that the antibacterial agent (C1) can improve the antibacterial effect against Gram-positive bacteria only for a specific composition containing a diiodomethane compound (A) and a cyclodextrin derivative (B).

Claims

1. An iodoform compound (A), a cyclodextrin derivative (B), and a compound (C), containing wherein the compound (C) comprises at least one selected from the group consisting of pyrrolidones, organic acids, terpenes, ureas and urea derivatives, alcohols, esters, chelate compounds, antioxidants, surfactants, and thioglycolic acid or a salt thereof, an antibacterial composition.

2. wherein the pyrrolidones are 1-methyl-2-pyrrolidone, the organic acids are oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, or propionic acid, the terpenes are limonene or menthol, the ureas and urea derivatives are urea or 1,3-diphenylurea, the alcohols are propylene glycol, glycerin, or isopropanol, the esters are isopropyl myristate, the chelate compound is calcium lignate, the antioxidant is tocopherol, the surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol, and the thioglycolic acid or a salt thereof is calcium thioglycolate trihydrate, the antibacterial composition according to Claim 1.

3. wherein the compound (C) comprises at least one selected from the group consisting of limonene, urea, propylene glycol, and polyoxyethylene polypropylene glycol, the antibacterial composition according to Claim 2.

4. wherein the iodoform compound (A) contains diiodomethyl-p-tolyl sulfone, the antibacterial composition according to Claim 1 or Claim 2.

5. wherein the cyclodextrin derivative (B) contains a β-cyclodextrin derivative (B1), the antibacterial composition according to Claim 1 or Claim 2.

6. wherein the β-cyclodextrin derivative (B1) contains methyl-β-cyclodextrin, the antibacterial composition according to Claim 5.

7. An antibacterial composition containing an iodoform compound, a cyclodextrin derivative, and an antibacterial agent.

8. Comprising at least one selected from the group consisting of 1-methyl-2-pyrrolidone, oleic acid, decanoic acid, lactic acid, tartaric acid, succinic acid, propionic acid, (R)-(+)-limonene, L-menthol, urea, 1,3-diphenylurea, propylene glycol, isopropanol, sorbitan monooleate, calcium lignate, calcium thioglycolate trihydrate, and polyoxyethylene polyoxypropylene glycol, An antibacterial agent used in a composition containing a diiodomethane compound and a cyclodextrin derivative.

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