Antimicrobial composition and antimicrobial active agent

Abstract

To provide an antimicrobial composition which exhibits superior antibacterial effects against at least one of Gram-positive bacteria and Gram-negative bacteria.SOLUTION: An antimicrobial composition of the present disclosure contains a diiodomethane compound (A) and a compound (B), wherein the compound (B) includes at least one selected from the group consisting of organic acids, terpenes, urea and urea derivatives, alcohols, esters, antioxidants, and surfactants.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 the 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 exhibiting 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 at least one of Gram-positive bacteria and Gram-negative bacteria may not be sufficient.

[0007] The problem to be solved by one embodiment of the present disclosure is to provide an antibacterial composition containing a diiodomethane compound that has an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria as compared with the case of using the diiodomethane compound alone.

Means for Solving the Problem

[0008] By adding a commercially available antibacterial agent to a composition containing a diiodomethane compound, 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 a composition containing a diiodomethane compound. As a result, although the reason is not clear, by adding a compound known to act on intercellular lipids to the diiodomethane compound, it was found that an antibacterial composition having an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria can be 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 compound (B), and the compound (B) contains at least one selected from the group consisting of organic acids, terpenes, ureas and urea derivatives, alcohols, esters, antioxidants, and surfactants, an antibacterial composition. <2> The organic acid is decanoic 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 antioxidant is tocopherol, The antibacterial composition according to <1> above, wherein the surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol. <3> The antibacterial composition according to <1> or <2> above, wherein the diiodomethane compound (A) contains diiodomethyl-p-toluenesulfone. <4> An antibacterial composition containing a diiodomethane compound and an antibacterial agent.

Advantages of the Invention

[0010] According to the present disclosure, there is provided an antibacterial composition having an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria.

Modes for Carrying Out the Invention

[0011] In the present disclosure, a numerical range represented using "~" means a range including the numerical values described before and after "~" as a lower limit value and an 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 another stepwise description. 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 a group (atomic group) in the present disclosure, a notation that does not describe substitution and non-substitution includes both those having no substituent and those having a substituent.

[0012] (1) First Embodiment The antibacterial composition of the present disclosure contains a diiodomethane compound (A) and a compound (B) (hereinafter also referred to as "antibacterial agent (B)"). The compound (B) includes at least one selected from the group consisting of organic acids, terpenes, ureas and urea derivatives, alcohols, esters, antioxidants, and surfactants.

[0013] The "antibacterial composition" refers to a composition having an antibacterial effect. 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 "organic acid" refers to an organic compound having at least one carboxyl group and ionizing to produce hydrogen ions. The "terpenes" refers to an organic compound having a skeleton of isoprene represented by the chemical formula CH 2 =C(CH 3 )CH=CH 2 The "urea and urea derivatives" refers to urea-based compounds containing urea or its derivatives, including urea and ureas having substituents. The "alcohols" refers to a compound in which at least one hydrogen atom of a hydrocarbon having a straight-chain, branched-chain or cyclic structure is substituted with a hydroxy group. The "esters" refers to an organic compound obtained by a dehydration condensation reaction between an organic compound containing a hydroxyl group and an organic compound having a carboxyl group. The "antioxidant" refers to an organic compound that contributes to a reaction that detoxifies by capturing reactive oxygen species (for example, oxygen free radicals, hydroxyl radicals, superoxide anions, hydrogen peroxide, etc.).

[0014] ​Since the antibacterial composition of the first embodiment has the above configuration, it is excellent as an antibacterial composition having an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria. The Gram-positive bacteria may be at least one of Staphylococcus aureus and Bacillus subtilis. The Gram-negative bacteria may be at least one of Escherichia coli and Pseudomonas aeruginosa.

[0015] The form of the antibacterial composition is not particularly limited, and examples include solutions (for example, aqueous solutions or non-aqueous solutions), suspensions (that is, slurry liquids), powders, pellets, and the like. The solution is obtained by dissolving the diiodomethane compound (A) in the solvent (C). Details of the solvent (C) 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 expressing a good antibacterial effect of the antibacterial composition, it preferably contains the compound (1) represented by the following general formula (1).

[0018] [Chemical formula]

[0019] In the 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] R 1The 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 straight-chain alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure, and is preferably a straight-chain 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 [alkyl group] 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 [halogen atom] include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0028] R 2 The substitution position of [substitution position] is not particularly limited. The substitution position of R 2 may be the ortho position, the meta position, or the para position based on the carbon atom to which L1 is bonded in the benzene ring of the general formula (1), and is preferably the 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 the commercially available product include "Yotole (registered trademark) DP95" (manufactured by Mitsui Chemicals, Inc., main component: DMTS).

[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, and still more preferably 1.0% by mass to 3.0% 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 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 based on 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 (blending ratio) of the diiodomethane compound (A).

[0035] (1.2) Compound (B) The antibacterial composition of the first embodiment contains an antibacterial agent (B).

[0036] The antibacterial agent (B) of the first embodiment contains at least one selected from the group consisting of organic acids, terpenes, ureas and urea derivatives, alcohols, esters, antioxidants, and surfactants.

[0037] Examples of the organic acid include fatty acids or their salts (for example, 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 their salts (for example, lactic acid, malic acid, sodium lactate, etc.), and carboxylic acids (for example, tartaric acid, succinic acid, propionic acid, salicylic acid, etc.). Examples of the terpenes include limonene (for example, (R)-(+)-limonene, etc.), menthol (for example, L-menthol, etc.), camphor, geraniol, etc. Examples of the urea derivatives include 1,3-diphenylurea, N,N'-dimethylpropyleneurea (DMPU), etc. Examples of the alcohols include polyhydric alcohols (for example, propylene glycol, glycerin, polyethylene glycol, 1,3-butylene glycol, dipropylene glycol, etc.), aliphatic alcohols (for example, oleyl alcohol, isostearyl alcohol, octyldodecanol, lauryl alcohol, myristyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, cetyl alcohol, cetanol, benzyl alcohol, etc.), and lower alcohols (for example, 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, and the like. Examples of the antioxidants include tocopherol (e.g., (±)-α-tocopherol, etc.), ascorbic acid, dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and the like. 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 tetrastearate, 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-acylsarcosine salt, and the like.

[0038] In the antibacterial active agent (B), it is preferable that the organic acid is decanoic 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 antioxidant is tocopherol, and the surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol. In other words, the antibacterial agent (B) is preferably at least one selected from the group consisting of decanoic acid, limonene, menthol, urea, 1,3-diphenylurea, propylene glycol, glycerin, isopropanol, isopropyl myristate, tocopherol, sorbitan monooleate, and polyoxyethylene polyoxypropylene glycol. Thereby, the antibacterial effect of the antibacterial composition against Gram-positive bacteria is more excellent.

[0039] (1.2.1) Content The content of the antibacterial agent (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 antibacterial agent (B) 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. When the form of the antibacterial composition is a solution, the content of the antibacterial agent (B) 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 (B) 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 (B) is regarded as the same as the addition ratio (blending ratio) of the antibacterial agent (B).

[0040] (1.3) Solvent The antibacterial composition of the first embodiment may further contain a solvent (C) in addition to the diiodomethane compound (A) and the antibacterial agent (B), or may not contain the solvent (C). When the antibacterial composition contains the solvent (C), 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.

[0041] Examples of the solvent (C) include aqueous solvents or non-aqueous solvents. The aqueous 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 non-aqueous solvent may be any solvent not containing water, and examples thereof include organic solvents and the like. 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.), and the like. These solvents may be used alone or in combination of two or more.

[0042] (1.3.1) Content The content of the solvent (C) 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 (C), the content of the solvent (C) 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 (C) is regarded as the same as the addition ratio (mixing ratio) of the solvent (C).

[0043] (1.4) Other components The antibacterial composition of the first embodiment may further contain other components (D) as needed, or may not contain other components (D), in addition to the diiodomethane compound (A) and the antibacterial agent (B). The other components (D) may be known components, for example, pH adjusters, defoamers, 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, and the like. These other components may be blended alone or in combination of two or more kinds.

[0044] (1.5) Target bacteria The bacteria against which the antibacterial composition of the first embodiment exhibits an antibacterial effect are at least one of Gram-positive bacteria and Gram-negative bacteria. Gram-positive bacteria include Staphylococcus aureus and Bacillus subtilis. Gram-negative bacteria include Escherichia coli and Pseudomonas aeruginosa.

[0045] (1.6) Uses of the antibacterial composition The antibacterial composition of the first embodiment can be used for various purposes. As uses of 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.), textile 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 metalworking fluids, detergents, cooling water, plating solutions, etc., cutting fluids for plastics or glass (e.g., lens processing fluids), 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 / related products / fur field (e.g., leather, etc.), ceramics / stone products field (e.g., ceramics such as tableware, etc.), electrical and mechanical appliances field (e.g., household electrical appliances such as refrigerators and air conditioners and their members, etc.), transportation machinery appliances field (e.g., automobiles and ships for logistics, etc.), precision machinery appliances field (e.g., high-tech devices and optical devices, 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 various fields.

[0046] Among these, the uses of the antibacterial composition are preferably in the fields of interior building materials, paints, inks, printing toners, wallpapers, adhesives, metalworking fluids, surface treatment agents, cutting fluids for plastics or glass (such as lens processing fluids), molded articles (such as films, sheets, and plastic products (such as resin moldings and synthetic leathers (such as polyurethane-based synthetic leathers)), fibers (clothes and futons), ceramics (tableware), paper and pulp products, detergents, deodorants, preservatives, and rubber products.

[0047] That is, by processing the members and products 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.

[0048] (1.7) Formulation of the antibacterial composition The antibacterial composition of the first embodiment may be used in 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, and products as described above. The dosage form obtained by formulation is not particularly limited, and various dosage forms such as aqueous, powder, and solvent systems (for example, oils, emulsions, solubilized preparations, wettable powders, flowables (aqueous suspensions, aqueous emulsions, etc.), microcapsule preparations, powders, tablets, aerosol preparations, and carbon dioxide gas preparations) are applicable. The antibacterial composition of the first embodiment can be formulated together with optional components generally used in formulation.

[0049] (2) Second embodiment The antibacterial composition according to the second embodiment of the present disclosure contains a diiodomethane compound and an antibacterial activator.

[0050] The diiodomethane compound is the same as those exemplified as the diiodomethane compound (A) of the first embodiment.

[0051] The "antibacterial activator" is an agent that exhibits an antibacterial effect in the antibacterial composition and does not include commercially available products of antibacterial agents at the time of filing this application.

[0052] Since the antibacterial composition of the second embodiment has the above configuration, it has an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria. The Gram-positive bacteria may be at least one of Staphylococcus aureus and Bacillus subtilis. The Gram-negative bacteria may be at least one of Escherichia coli and Pseudomonas aeruginosa.

[0053] 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.

[0054] (2.1) Antibacterial agent In addition to those exemplified as the antibacterial agent (B) of the first embodiment, the antibacterial agent of the second embodiment includes amines (such as monoethanolamine, diethanolamine, triethanolamine, etc.), AZONEs (such as AZONE, etc.), enamine derivatives, polyamines, polycations (such as polyarginine, polyethyleneimine, etc.), chitosans (such as chitosan, etc.), hydrocarbon oils (such as liquid paraffin, etc.), silicone oils (such as dimethyl silicone oil, methylphenyl silicone oil, methylhydrogen silicone oil, etc.), dendrimers, and membrane-permeable peptides.

[0055] (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 and the antibacterial agent. The solvent is the same as that exemplified as the solvent (C) of the first embodiment.

[0056] (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 and the antibacterial agent. The other components are the same as those exemplified as the other components (D) of the first embodiment.

[0057] (2.4) Target bacteria The bacteria against which the antibacterial composition of the second embodiment exhibits antibacterial effect are Gram-positive bacteria. Gram-positive bacteria include Staphylococcus aureus and Bacillus subtilis. The antibacterial composition of the second embodiment also exhibits antibacterial effect against Gram-negative bacteria as shown in the following examples. Gram-negative bacteria include Escherichia coli.

[0058] (2.5) Use of the antibacterial composition The use of the antibacterial composition of the second embodiment is not particularly limited, and examples include the same as those exemplified as the use of the antibacterial composition of the first embodiment.

[0059] (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 as those exemplified as the formulation of the antibacterial composition of the first embodiment.

Examples

[0060] Hereinafter, the present disclosure will be described more specifically by way of 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.

[0061] [1] Raw materials The products used in the examples, reference examples and comparative examples are as follows.

[0062] [1.1] Diiodomethane compound (A) · DMTS: “Yotole (registered trademark) DP95” manufactured by Mitsui Chemicals, Inc. (component: diiodomethyl-p-toluenesulfone, form: powder) was used.

[0063] [1.2] Antibacterial agent (B) · Decanoic 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 · POE polyoxypropylene glycol: Polyoxyethylene polyoxypropylene glycol

[0064] [1.3] Solvent (C) · DMSO: Dimethyl sulfoxide

[0065] [2] Examples and Comparative Examples of Antibacterial Compositions [2.1] Examples 1 to 12 and Comparative Examples 1 to 13 The diiodomethane compound (A), antibacterial agent (B), and solvent (C) shown in Tables 1 and 2 were mixed at the ratios shown in Tables 1 and 2 to obtain an antibacterial composition.

[0066] [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.

[0067] [2.2.1] Evaluation of Antibacterial Effect The antibacterial effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0068] [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.

[0069] [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 LB medium autoclaved at 121°C for 20 minutes.

[0070] 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) Bacterial species (a4): Pseudomonas aeruginosa (NBRC 3080, distributing agency: National Institute of Technology and Evaluation, Pseudomonas aeruginosa)

[0071] [2.2.1.3] Sample preparation The antibacterial compositions shown in Table 1 and Table 2 were added to 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, a culture medium containing the antibacterial composition was obtained. Note that for Pseudomonas aeruginosa (Pseudomonas aeruginosa) only, the maximum concentration of the active ingredient was 4000 ppm. The "maximum concentration of the active ingredient" in the MIC test method (bacteria) in Table 1 indicates the ratio (mass %) of the mass of (B) in the culture medium containing the antibacterial composition calculated from the blending amount of the antibacterial agent (B) to the total mass of the culture medium containing the antibacterial composition. The "maximum concentration of the active ingredient" in the MIC test method (bacteria) in Table 2 indicates the ratio (mass %) of the mass of (A) in the culture medium containing the antibacterial composition calculated from the blending amount of the diiodomethane compound (A) to the total mass of the culture medium containing the antibacterial composition.

[0072] [2.2.1.4] Bacterial solution preparation The test bacterial strain was suspended in an LB medium that had been autoclaved and sterilized at 121°C for 20 minutes, and adjusted so that the O.D. (Optical Density) of the suspension was 1.0 - 2.0. Thereby, a bacterial solution was obtained.

[0073] [2.2.1.5] MIC Measurement (Bacteria) To each 100 μL of the dilution series of the medium containing the antibacterial composition, 2 μL of the bacterial solution of the bacterial strains described in Tables 1 and 2 was inoculated, and cultured under the conditions of 35°C for 18 to 24 hours. The growth of the bacteria was visually confirmed, and the minimum dilution concentration without the growth of the bacteria was taken as the MIC value. When the medium containing the antibacterial composition was clear, it was judged that there was no growth of the bacteria. The lower the MIC value, the more excellent the antibacterial effect. Note that the MIC values described in Table 1 refer to the MIC values of the antibacterial agent, and the MIC values described in Table 2 refer to the MIC values of the diiodomethane compound (DMTS).

[0074] The MIC test (bacteria) was carried out 3 times in total. When the MIC values of the 3 MIC tests (bacteria) were different and the MIC values were within the measurement range, the 3 MIC values were described in Tables 1 and 2. When the MIC values of the 3 MIC tests (bacteria) were different and some of them were outside the measurement range and the numerical values could not be specified, they were described in Tables 1 and 2 in the form of ">1000". ">1000" indicates that the minimum value of the MIC value exceeded 1000 ppm.

[0075] [2.2.2] Evaluation of Antifungal Effect The antifungal effect of the antibacterial composition was evaluated by the MIC (Minimum Inhibitory Concentration) test method.

[0076] [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 was 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 was 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 was 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.

[0077] [2.2.2.2] Pre-culture In the MIC test (fungus), the following fungal species (b1) were used. The fungal species (b1) were test fungal species cultured at 25°C for 7 days or more using PDA medium autoclaved at 121°C for 20 minutes.

[0078] Fungal species (b1): Aspergillus niger (NBRC 105649, distributing agency: National Institute of Technology and Evaluation, black mold)

[0079] [2.2.2.3] Sample preparation The antibacterial compositions shown in Table 1 and Table 2 were added to PDB medium autoclaved at 121°C for 20 minutes to prepare an 11-step two-fold dilution series with the maximum concentration of the active ingredient set at 100 ppm. 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 ratio (mass %) of the mass of the antibacterial agent (B) in the antibacterial composition-containing medium calculated from the amount of the antibacterial agent (B) blended with respect to the total mass of the antibacterial composition-containing medium. In Table 2, the "maximum concentration of active ingredient" in the MIC test method (fungus) 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.

[0080] [2.2.2.4] Fungus liquid preparation The test fungus species was suspended in a surfactant solution autoclaved at 121 °C for 20 minutes, and the spore count was adjusted to 1×10 5 / mL to 100×10 5 / mL using a hemocytometer. Thus, a fungus liquid was obtained.

[0081] [2.2.2.5] MIC measurement (fungus) 100 μL of the fungus liquid 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 clumps of the mycelium of the fungus 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 more excellent the antifungal effect is indicated.

[0082] The MIC test (fungus) was carried out 2 times in total. When the MIC values actually measured in the two MIC tests (fungus) were different, the two MIC values were described in Table 1 and Table 2.

[0083] [2.2.2] Evaluation results

Table 1

[0084]

Table 2

[0085] In Tables 1 and 2, “(A)” represents the diiodomethane compound (A). “(B)” represents the antibacterial agent (B). “(C)” represents the solvent (C). “S.aureus” represents Staphylococcus aureus. “B.subtilis” represents Bacillus subtilis. “E.coli” represents Escherichia coli. “P.aeruginosa” represents Pseudomonas aeruginosa. “A.niger” represents Aspergillus niger. The “*” for the MIC value of Staphylococcus aureus in Comparative Example 5 in Table 1 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.

[0086] In Comparative Examples 1 to 13, the antibacterial composition contained the antibacterial agent (B) and did not contain the diiodomethane compound (A). In Examples 1 to 12, the antibacterial composition contained the diiodomethane compound (A) and the antibacterial agent (B).

[0087] Hereinafter, the MIC value against Staphylococcus aureus is also referred to as “MIC value (S.aureus)”. The MIC value against Bacillus subtilis is also referred to as “MIC value (B.subtilis)”. The MIC value against Escherichia coli is also referred to as “MIC value (E.coli)”. The MIC value against Pseudomonas aeruginosa is also referred to as “MIC value (P.aeruginosa)”. The MIC value against Aspergillus niger is also referred to as “MIC value (A.niger)”.

[0088] The MIC value (P.aeruginosa) of Example 1 was lower than the MIC value (P.aeruginosa) of Comparative Example 1. That is, it was found that the antibacterial composition of Example 1 has a superior antibacterial effect against Gram-negative bacteria than Comparative Example 1.

[0089] The MIC value (B.subtilis) of Example 2 was lower than the MIC value (B.subtilis) of Comparative Example 2. That is, it was found that the antibacterial composition of Example 2 has a superior antibacterial effect against Gram-positive bacteria than Comparative Example 2.

[0090] The MIC value of Example 3 (B. subtilis) was lower than that of Comparative Example 3 (B. subtilis). The MIC value of Example 3 (E. coli) was lower than that of Comparative Example 3 (E. coli). That is, it was found that the antibacterial composition of Example 3 was superior in antibacterial effect against each of Gram-positive bacteria and Gram-negative bacteria than Comparative Example 3.

[0091] The MIC value of Example 4 (B. subtilis) was lower than that of Comparative Example 4 (B. subtilis). The MIC value of Example 4 (P. aeruginosa) was lower than that of Comparative Example 4 (P. aeruginosa). That is, it was found that the antibacterial composition of Example 4 was superior in antibacterial effect against each of Gram-positive bacteria and Gram-negative bacteria than Comparative Example 4.

[0092] The MIC value of Example 5 (P. aeruginosa) was lower than that of Comparative Example 5 (P. aeruginosa). That is, it was found that the antibacterial composition of Example 5 was superior in antibacterial effect against Gram-negative bacteria than Comparative Example 5.

[0093] The MIC value of Example 6 (S. aureus) was lower than that of Comparative Example 6 (S. aureus). The MIC value of Example 6 (B. subtilis) was lower than that of Comparative Example 6 (B. subtilis). The MIC value of Example 6 (E. coli) was lower than that of Comparative Example 6 (E. coli). That is, it was found that the antibacterial composition of Example 6 was superior in antibacterial effect against each of Gram-positive bacteria and Gram-negative bacteria than Comparative Example 6.

[0094] The MIC value of Example 7 (S. aureus) was lower than that of Comparative Example 7 (S. aureus). The MIC value of Example 7 (E. coli) was lower than that of Comparative Example 7 (E. coli). That is, it was found that the antibacterial composition of Example 7 was superior in antibacterial effect against each of Gram-positive bacteria and Gram-negative bacteria than Comparative Example 7.

[0095] The MIC value (E. coli) of Example 8 was lower than that of Comparative Example 8. That is, it was found that the antibacterial composition of Example 8 had an antibacterial effect on Gram-negative bacteria superior to that of Comparative Example 8.

[0096] The MIC value (S. aureus) of Example 9 was lower than that of Comparative Example 9. That is, it was found that the antibacterial composition of Example 9 had an antibacterial effect on Gram-positive bacteria superior to that of Comparative Example 9.

[0097] The MIC value (S. aureus) of Example 10 was lower than that of Comparative Example 10. That is, it was found that the antibacterial composition of Example 10 had an antibacterial effect on Gram-positive bacteria superior to that of Comparative Example 10.

[0098] The MIC value (S. aureus) of Example 11 was lower than that of Comparative Example 11. The MIC value (B. subtilis) of Example 11 was lower than that of Comparative Example 11. That is, it was found that the antibacterial composition of Example 11 had an antibacterial effect on Gram-positive bacteria superior to that of Comparative Example 11.

[0099] The MIC value (S. aureus) of Example 12 was lower than that of Comparative Example 12. The MIC value (E. coli) of Example 12 was lower than that of Comparative Example 12. The MIC value (P. aeruginosa) of Example 12 was lower than that of Comparative Example 12. That is, it was found that the antibacterial composition of Example 12 had an antibacterial effect on each of Gram-positive bacteria and Gram-negative bacteria superior to that of Comparative Example 12.

[0100] As a result of these, it was found that the antibacterial compositions of Examples 1 to 12 were "antibacterial compositions having an excellent antibacterial effect against at least one of Gram-positive bacteria and Gram-negative bacteria".

Claims

1. A composition containing a diiodomethane compound (A) and a compound (B), wherein the compound (B) contains at least one selected from the group consisting of organic acids, terpenes, ureas and urea derivatives, alcohols, esters, antioxidants, and surfactants, and is an antibacterial composition.

2. The organic acid is decanoic 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 antioxidant is tocopherol, the surfactant is sorbitan monooleate or polyoxyethylene polyoxypropylene glycol, and the antibacterial composition according to Claim 1.

3. The antibacterial composition according to Claim 1 or Claim 2, wherein the diiodomethane compound (A) contains diiodomethyl-p-toluenesulfone.

4. An antibacterial composition containing a diiodomethane compound and an antibacterial agent. ​

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