Microbial control composition

Abstract

To provide a microorganism control composition that exhibits excellent microorganism control effect even in use environments such as industrial applications and sanitary goods applications.SOLUTION: The microorganism control composition contains the following components (a) and (b): a component (a) being one or more selected from quinolone-based compounds represented by general formula (1) in the figure and salts thereof; and a component (b) being zeolite where the molar ratio of SiO2 / Al2O3 is 10 or more.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a microbial control composition. [Background technology]

[0002] Quinolone compounds are well-known antibacterial agents that are essential for the treatment of infectious diseases. The new quinolones, which emerged after norfloxacin, offer significantly improved antibacterial spectrum and potency compared to the old quinolones, such as nalidixic acid and pipemidic acid, which primarily exhibited antibacterial activity against gram-negative bacteria. Both quinolone compounds and new quinolone compounds are used for the treatment and diagnosis of human infectious diseases (e.g., Patent Documents 1 and 2), and norfloxacin is also used for non-medical purposes, such as as a seed disinfectant in the agricultural chemical field (Patent Document 3). On the other hand, attempts to use new quinolone compounds with excellent antibacterial activity at lower dosages have also been proposed. For example, Patent Document 4 discloses an antibacterial agent that uses a new quinolone compound such as norfloxacin in combination with a lactoferrin hydrolysate or an antibacterial peptide derived from a lactoferrin hydrolysate. However, although the antibacterial agent disclosed in Patent Document 4 is an antibacterial agent that can obtain strong antibacterial activity at a small dose for pharmaceutical use, has few side effects, and can reduce the frequency of emergence of resistant bacteria, it cannot be used in the same way in usage environments such as industrial use. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 08-193024 [Patent Document 2] Japanese Patent Application Publication No. 09-243637 [Patent Document 3] Japanese Patent Application Publication No. 05-155718 [Patent Document 4] Japanese Patent Application Publication No. 11-092375 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a microorganism control composition that exhibits excellent microorganism control effects even in use environments such as industrial and sanitary product applications. [Means for solving the problem]

[0005] As a result of extensive research conducted by the present inventors to solve the above-mentioned problems, they discovered that when a quinolone compound or a salt thereof is used in combination with a zeolite having a SiO2 / Al2O3 (molar ratio) of 10 or more, the antibacterial activity is significantly improved to an extent that cannot be achieved by the quinolone compound or its salt alone, even though the zeolite has no antibacterial effect, and that a microorganism control composition with excellent effects can be produced, thereby solving the above-mentioned problems.

[0006] Specifically, the present invention provides the following: 1. A microorganism control composition comprising the following component (a) and the following component (b): Component (a): one or more quinolone compounds represented by the following general formula (1) and salts thereof: Component (b): Zeolite with SiO2 / Al2O3 (molar ratio) of 10 or more [ka] (In the formula, ring A represents a 6-membered aromatic ring which may be substituted and which may be a heterocyclic ring in which one or two carbon atoms are substituted with nitrogen atoms; R1 and R2 may be the same or different and represent a hydrogen atom or an optionally substituted hydrocarbon group; and R1 may form a ring together with the substituent of ring A.) 2. The microorganism control composition described in 1., wherein the quinolone compound is one or more compounds selected from the group consisting of compounds represented by the following general formula (2) and compounds represented by the following general formula (3): [ka] (In the formula, R1 and R2 are the same or different and each represent a hydrogen atom or an optionally substituted hydrocarbon group; R3 represents a hydrogen atom, a halogen atom, or an amino group; R4 represents a hydrogen atom or a halogen atom; and R5 represents an optionally substituted hydrocarbon group or an optionally substituted cyclic amino group.) [ka] (In the formula, R1 and R2 are the same or different and represent a hydrogen atom or an optionally substituted hydrocarbon group; R3 represents a hydrogen atom, a halogen atom, or an amino group; R4 represents a hydrogen atom or a halogen atom; R5 represents an optionally substituted hydrocarbon group or an optionally substituted cyclic amino group; and R6 represents a hydrogen atom, a halogen atom, an optionally substituted alkoxy group, or an optionally substituted hydrocarbon group. R4 may form an alkylenedioxy group together with R5, and R1 may form a ring together with R6.) 3. The microorganism control composition according to 1, wherein the quinolone compound is one or more selected from the group consisting of enoxacin, tosufloxacin, oxolinic acid, nalidixic acid, norfloxacin, sarafloxacin, difloxacin, fleroxacin, lomefloxacin, enrofloxacin, ciprofloxacin, gatifloxacin, sparfloxacin, danofloxacin, moxifloxacin, garenoxacin, sitafloxacin, orbifloxacin, nadifloxacin, ofloxacin, levofloxacin, pazufloxacin, marbofloxacin, piromidic acid, and pipemidic acid. 4. The microorganism control composition according to any one of 1 to 3, wherein the zeolite is an MFI type zeolite. 5. A product containing the microbial control composition described in any one of 1. to 4. 6. A method for producing a microorganism control material by applying the microorganism control composition according to any one of 1. to 4. to a material. [Effects of the Invention]

[0007] The microbial control composition of the present invention exhibits excellent microbial control activity and can be applied to a variety of industrial products and materials. For example, the composition can be incorporated in small amounts as an additive that exhibits antibacterial activity into indoor and outdoor paints, rubber, fibers, resins, plastics, adhesives, joint compounds, sealants, building materials, caulking agents, soil treatment agents, wood treatment agents, white water in the papermaking process, pigments, printing plate treatment solutions, cooling water, inks, cutting oils, nonwoven fabrics, spinning oils, leather, etc., and can therefore exhibit excellent microbial control activity. Furthermore, the microorganism control composition of the present invention exhibits excellent deodorizing effect in addition to excellent microorganism control activity, and is therefore suitable for use in sanitary products such as disposable diapers to suppress unpleasant odors. DETAILED DESCRIPTION OF THE INVENTION

[0008] The microorganism control composition of the present invention, as well as a product containing the microorganism control composition and a method for applying the microorganism control composition to produce a microorganism control material, will be described in detail below. <About ingredient (a)> The microorganism control composition of the present invention contains, as component (a), one or more compounds selected from the group consisting of quinolone compounds represented by the following general formula (1) and salts thereof. [ka] (In the formula, ring A represents a 6-membered aromatic ring which may be substituted and which may be a heterocyclic ring in which one or two carbon atoms are substituted with nitrogen atoms; R1 and R2 may be the same or different and represent a hydrogen atom or an optionally substituted hydrocarbon group; and R1 may form a ring together with the substituent of ring A.)

[0009] In the general formula (1), among the "6-membered aromatic ring which may be substituted and may be a heterocyclic ring in which one or two carbon atoms are substituted with nitrogen atoms" represented by ring A, examples of the 6-membered aromatic ring which is a heterocyclic ring include pyridine, pyrimidine, pyridazine, pyrazine, etc., and examples of the 6-membered aromatic ring which is not a heterocyclic ring include benzene. Among these, benzene, pyridine, and pyrimidine are preferred, and benzene or pyridine is particularly preferred. Substituents for the "optionally substituted 6-membered aromatic ring which may be a heterocyclic ring in which one or two carbon atoms are substituted with nitrogen atoms" represented by Ring A include a hydroxyl group, a halogen atom, an optionally substituted alkoxy group, an optionally substituted hydrocarbon group, an optionally substituted amino group, an alkylenedioxy group, etc. Examples of halogen atoms include fluorine, chlorine, bromine and iodine atoms, with fluorine and chlorine atoms being preferred. The alkoxy group of the "optionally substituted alkoxy group" includes an alkoxy group having 1 to 6 carbon atoms, and is preferably an alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, etc. Substituents of the "optionally substituted alkoxy group" include halogen atoms such as fluorine, chlorine, and bromine; alkoxy groups having 1 to 4 carbon atoms; and aryl groups having 1 to 14 carbon atoms, such as phenyl and naphthyl. The hydrocarbon group of the "optionally substituted hydrocarbon group" is preferably a hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrocarbon group having 1 to 14 carbon atoms, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group, and an aralkyl group.

[0010] Examples of the alkyl group include alkyl groups having 1 to 10 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 1-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, n-hexyl, isohexyl, 1-ethyl-1-methylpropyl, 2-ethylbutyl, n-heptyl, isoheptyl, 2,2-dimethylpentyl, n-octyl, isooctyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1,1-dimethylhexyl, 1-ethyl-1-methylpentyl, 1,1-diethylbutyl, 2-ethylhexyl, nonyl, and decyl, and preferably alkyl groups having 1 to 8 carbon atoms. Examples of the alkenyl group include alkenyl groups having 2 to 6 carbon atoms, such as ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl. Examples of the alkynyl group include alkynyl groups having 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, and 5-hexynyl. Examples of the cycloalkyl group include cycloalkyl groups having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of the aryl group include aryl groups having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl, and phenanthrenyl. Examples of the aralkyl group include aralkyl groups having 7 to 14 carbon atoms, such as benzyl, phenylethyl, and naphthylmethyl.

[0011] Substituents of the above-mentioned "optionally substituted hydrocarbon group" include a hydroxyl group; halogen atoms such as chlorine, fluorine, bromine and iodine; a cyano group; an amino group; a carboxyl group; an acyl group having 1 to 6 carbon atoms such as acetyl, propanoyl, butanoyl, hexanoyl, etc.; an alkoxy group having 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, etc.; an aryloxy group having 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms, such as phenoxy, naphthyloxy, etc.; Examples include aralkyloxy groups having 7 to 14 carbon atoms such as thio and phenylethyloxy; alkylthio groups having 1 to 4 carbon atoms such as methylthio, ethylthio, propylthio and butylthio; and arylthio groups having 6 to 20 carbon atoms such as phenylthio. The hydrocarbon group may have two or more of the above-mentioned substituents, and the substituents may be the same or different.

[0012] The amino group of the "optionally substituted amino group" includes cyclic amino groups such as pyrrolidinyl, piperidyl, piperazinyl, azabicyclo[2.2.1]heptanyl, azabicyclo[2.2.2]octanyl, diazabicyclo[2.2.1]heptanyl, diazabicyclo[2.2.2]octanyl, octahydropyrrolopyridinyl, isoindolinyl, and azaspiro[2.4]heptanyl, with piperazinyl or pyrrolidinyl being preferred. Examples of the substituent of the "optionally substituted amino group" include a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, and an amino group. As the "alkylenedioxy group", one having an alkylene group having 1 to 4 carbon atoms is preferred, a methylenedioxy group or an ethylenedioxy group is more preferred, and a methylenedioxy group is particularly preferred.

[0013] Ring A is preferably substituted with 2 to 4 substituents. Preferred examples of the substituents include a halogen atom, a cycloalkyl group having 3 to 6 carbon atoms substituted with an amino group, a cyclic amino group such as pyrrolidinyl, piperidyl, piperazinyl, diazabicyclo[2.2.1]heptanyl, octahydropyrrolopyridinyl, isoindolinyl, and azaspiro[2.4]heptanyl, the above cyclic amino group substituted with a hydroxyl group, an amino group, or an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and the above alkoxy group substituted with a halogen atom. Furthermore, preferred examples of the substituent on ring A include alkylenedioxy groups having 1 to 4 carbon atoms. As such alkylenedioxy groups, methylenedioxy groups or ethylenedioxy groups are more preferred, and methylenedioxy groups are particularly preferred.

[0014] In the above general formula (1), examples of the "optionally substituted hydrocarbon group" represented by R1 or R2 include the same groups as the "optionally substituted hydrocarbon group" of ring A described above. In addition, the group represented by R1 may form a ring together with the substituent at the 8-position of ring A. Examples of such a ring include a hydropyridine ring, a hydroxazine ring, and a hydrooxadiazine ring.

[0015] Component (a) in the present invention is preferably one or more compounds selected from the group consisting of compounds represented by the following general formula (2) and compounds represented by the following general formula (3). [ka] (wherein R1 and R2 are the same or different and represent a hydrogen atom or an optionally substituted hydrocarbon group; R3 is a hydrogen atom, a halogen atom, or an amino group; R4 is a hydrogen atom or a halogen atom; and R5 is an optionally substituted hydrocarbon group or an optionally substituted cyclic group.) It indicates an amino group. [ka] (In the formula, R1 and R2 are the same or different and represent a hydrogen atom or an optionally substituted hydrocarbon group, R3 represents a hydrogen atom, a halogen atom or an amino group, R4 represents a hydrogen atom or a halogen atom, R5 represents an optionally substituted hydrocarbon group or an optionally substituted cyclic amino group, and R6 represents a hydrogen atom, a halogen atom, an optionally substituted alkoxy group or an optionally substituted hydrocarbon group. In addition, R4 may form an alkylenedioxy group together with R5, and R1 may form a ring together with R6.

[0016] The compound represented by the general formula (2) is a compound having a naphthyridine skeleton, and the compound represented by the general formula (3) includes a compound having a quinoline skeleton. In the above general formulas (2) and (3), the group represented by R1 or R2 has the same meaning as R1 or R2 in the above general formula (1). Examples of the halogen atom represented by R3 or R4 include a fluorine atom, a chlorine atom, and a bromine atom. The same applies to the "optionally substituted hydrocarbon group" and "optionally substituted cyclic amino group" represented by R5. In addition, in the above general formulas (2) and (3), the group represented by R1 is preferably an alkyl group having 1 to 4 carbon atoms such as ethyl; a halogenated alkyl group having 1 to 4 carbon atoms such as 2-fluoroethyl; a cycloalkyl group having 3 to 6 carbon atoms such as cyclopropyl, cyclopentyl, and cyclohexyl; a halogenated cycloalkyl group having 3 to 6 carbon atoms such as fluorocyclopropyl; or a halogenated aryl group such as fluorophenyl or difluorophenyl. The group represented by R2 is preferably a hydrogen atom, the group represented by R3 is preferably a hydrogen atom, a fluorine atom, or an amino group, and the group represented by R4 is preferably a hydrogen atom or a fluorine atom. The group represented by R5 is preferably an aminocyclopropyl group; pyrrolidinyl, piperidyl, piperazinyl, diazabicyclo[2.2.1]heptyl, octahydropyrrolopyridinyl, isoindolinyl, or azaspiro[2.4]heptanyl substituted with a hydroxyl group, an amino group, or an alkyl group having 1 to 4 carbon atoms such as methyl or ethyl.

[0017] Furthermore, the same applies to the "optionally substituted alkoxy group" and "optionally substituted hydrocarbon group" represented by R6 in the above general formula (3). In the above general formula (3), the group represented by R6 is preferably a hydrogen atom; a halogen atom such as a fluorine atom or a chlorine atom; an alkyl group having 1 to 4 carbon atoms such as methyl; an alkoxy group having 1 to 4 carbon atoms such as methoxy; or the above alkoxy group substituted with a halogen atom such as difluoromethoxy. In addition, in the above general formula (3), R4 may form an alkylenedioxy group together with R5, and the "alkylenedioxy group" is the same as above. Furthermore, in the above general formula (3), the group represented by R1 may form a ring together with the group represented by R6, and examples of such a ring include a hydropyridine ring, a hydroxazine ring, and a hydroxadiazine ring. Therefore, in the above general formula (3), compounds having a benzoquinolizine skeleton, a pyridobenzoxazine skeleton, or a pyridobenzoxadiazine skeleton formed by the group represented by R1 and the group represented by R6 forming a ring are also exemplified as preferred compounds. do.

[0018] In addition to the compounds represented by general formulas (2) and (3), the compound represented by the following general formula (4) is also suitable as component (a) in the present invention. That is, component (a) in the present invention is preferably one or more compounds selected from the group consisting of compounds represented by the following general formulas (2) to (4). [ka] (In the formula, R1 and R2 are the same or different and each represent a hydrogen atom or an optionally substituted hydrocarbon group, R3 represents a hydrogen atom, a halogen atom, or an amino group, and R5 represents an optionally substituted hydrocarbon group or an optionally substituted cyclic amino group.) The definitions and specific examples of R1 to R3 and R5 in general formula (4) are the same as those in general formulas (1) to (3). In the compound represented by general formula (4), the group represented by R2 is preferably a hydrogen atom, the group represented by R3 is preferably a hydrogen atom, a fluorine atom, or an amino group, and the group represented by R5 is preferably an aminocyclopropyl group; pyrrolidinyl, piperidyl, piperazinyl, diazabicyclo[2.2.1]heptyl, octahydropyrrolopyridinyl, isoindolinyl, or azaspiro[2.4]heptanyl substituted with a hydroxyl group, an amino group, or an alkyl group having 1 to 4 carbon atoms such as methyl or ethyl.

[0019] Suitable examples of component (a) in the present invention include compounds represented by the above general formula (1), such as enoxacin and tosufloxacin, which have a naphthyridine skeleton, oxolinic acid, which have a quinoline skeleton, norfloxacin, sarafloxacin, difloxacin, fleroxacin, lomefloxacin, enrofloxacin, ciprofloxacin, gatifloxacin, sparfloxacin, danofloxacin, moxifloxacin, garenoxacin, sitafloxacin, orbifloxacin, nadifloxacin, which have a benzoquinolizine skeleton, ofloxacin, levofloxacin, pazufloxacin, marbofloxacin, which have a pyridobenzoxazine skeleton, pipemidic acid and piromidic acid, which have a pyridopyrimidine skeleton, and nalidixic acid, which have a naphthyridine skeleton. One or more of these compounds may be selected for use. Among these, norfloxacin, ofloxacin, levofloxacin, lomefloxacin, enoxacin, tosufloxacin, oxolinic acid, nalidixic acid, piromidic acid, and pipemidic acid are preferred as component (a), norfloxacin, ofloxacin, levofloxacin, oxolinic acid, nalidixic acid, and piromidic acid are more preferred, and norfloxacin and oxolinic acid are particularly preferred. Oxolinic acid is preferred from the viewpoint of heat resistance and water resistance, and norfloxacin is preferred from the viewpoint of safety to humans. The microorganism control composition of the present invention containing oxolinic acid and / or norfloxacin is suitable for application to various industrial products and industrial materials, and for application as a deodorizer to sanitary products such as disposable diapers.

[0020] Component (a) in the present invention can also be used in the form of a pharmaceutically acceptable salt, such as a salt with an inorganic acid such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, or phosphoric acid; a salt with an organic acid such as formic acid, acetic acid, trifluoroacetic acid, phthalic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, malic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenesulfonic acid; a salt with an alkali metal such as sodium or potassium; a salt with an alkaline earth metal such as magnesium or calcium; an ammonium salt; or a salt with an organic amine such as trimethylamine, triethylamine, pyridine, picoline, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, 1,6-hexamethylenediamine, tert-butylamine, cyclohexylamine, benzylamine, dicyclohexylamine, or N,N-dibenzylethylenediamine.

[0021] <About ingredient (b)> The microorganism control composition of the present invention contains, as component (b), a zeolite with an SiO2 / Al2O3 (molar ratio) of 10 or more. Zeolite is a crystalline porous material with a basic skeleton of SiO2 and Al2O3, and has uniform pores of about 0.1 to 1.0 nm in each skeleton structure, characterized by a sharper pore distribution than activated carbon or silica gel. Component (b) in the present invention contains a zeolite called a high-silica zeolite having a SiO2 / Al2O3 (molar ratio) of 10 or more, preferably a zeolite having a SiO2 / Al2O3 (molar ratio) of 30 or more, and more preferably a zeolite having a SiO2 / Al2O3 (molar ratio) of 50 or more. Among these, MFI-type zeolite is suitable as component (b) in the present invention. The molar ratio (SiO2 / Al2O3) of silica (SiO2) to alumina (Al2O3) in high-silica zeolite can be calculated from quantitative analysis of elements by, for example, inductively coupled plasma atomic emission spectroscopy (ICP-AES). Component (b) in the present invention can be produced by the method described in prior art documents (e.g., International Publication No. 2017 / 142033, etc.), and commercially available products such as Mizuka Sieves EX122, Silton MT-100, MT-400, and MT-8000 can also be used.

[0022] <Regarding the microbial control composition of the present invention> In the microorganism control composition of the present invention, the weight ratio of the component (a) to the component (b) is preferably within the range of 0.1:99.9 to 50:50 (weight ratio), and more preferably 0.2:99.8 It is more preferable that the weight ratio is within the range of 0.5:99.5 to 30:70, and particularly preferably within the range of 0.5:99.5 to 20:80. The experiments described below have confirmed that when component (a) one or more quinolone compounds represented by the above general formula (1) or salts thereof is combined with component (b) zeolite having an SiO2 / Al2O3 (molar ratio) of 10 or more, the antibacterial activity is significantly improved to an extent that cannot be achieved by component (a) alone, even though component (b) zeolite has no antibacterial effect at all. In other words, an extremely excellent activation effect of component (a) is obtained that far exceeds the effect expected when simply applying component (a) and component (b) alone. Although the details of the mechanism of action by which the combination in the microorganism control composition of the present invention exhibits the extremely excellent activation effect of component (a) are unknown, it is presumed that such a remarkable effect is achieved by combining components (a) and (b), which produces an extremely excellent activation effect at the level of the action site where the mechanism of action of component (a) is expressed. Therefore, this extremely excellent activation effect of component (a) can only be achieved by combining components (a) and (b), and this is an especially remarkable effect that the present inventors have confirmed for the first time.

[0023] The microorganism control composition of the present invention can be prepared in various formulation forms by dispersing component (a) and component (b) in various carriers, such as liquid carriers or solid carriers. Examples include liquid formulations such as wettable powders, suspensions, dispersions, emulsions, and oils; solid formulations such as dusts, granules, microcapsules, microspheres, flowables, and foams; semisolid formulations such as pastes and creams; sprays, aerosols, and paints, which can be selected appropriately depending on the purpose of use and the conditions of application. These formulations can be prepared by conventional methods.

[0024] Examples of the liquid carrier that can be used in the present invention include water; lower alcohols such as methanol, ethanol, n-propanol, isopropanol, and n-butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, ethylene glycol monomethyl ether (methyl carbitol), ethylene glycol monoethyl ether (ethyl carbitol), ethylene glycol monobutyl ether (butyl carbitol), diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and triethylene glycol butyl ether; acetone, methyl ethyl Examples of suitable liquid carriers include ketones such as ketone, methyl isobutyl ketone, and propylene carbonate; ethers such as dioxane, tetrahydrofuran, and ethyl ether; esters such as ethyl acetate, butyl acetate, isobutyl acetate, 3-methyl-3-methoxybutyl acetate, γ-butyrolactone, dimethyl adipate, dimethyl glutarate, and dimethyl succinate; aromatic solvents such as benzene, toluene, xylene, methylnaphthalene, dimethylnaphthalene, isopropylnaphthalene, diisopropylnaphthalene, ethylbiphenyl, diethylbiphenyl, and solvent naphtha; halogenated hydrocarbon solvents such as carbon tetrachloride, chloroform, and methylene chloride; and polar organic solvents such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide, acetonitrile, and N-methylpyrrolidone. These liquid carriers may be used alone or in combination. Among these liquid carriers, water, ketones such as propylene carbonate, lower alcohols, and polyhydric alcohols are preferred.

[0025] Examples of the solid carrier that can be used in the present invention include diatomaceous earth, mica, clay, kaolin, talc, silica, bentonite, talc powder, rosewood powder, and other talcs, clays such as finely powdered clay, and mineral powders such as calcium carbonate; sulfur powder; urea powder; plant powders such as wood flour and starch; and various carriers commonly used in microbial control compositions. These solid carriers are often used as extenders. These solid carriers can also be used in one or more types. The above can be mixed and used. The aerosol preparation can be produced by diluting component (a) and component (b) with an appropriate solvent as needed and filling the dilution with a propellant into a container. Examples of the solvent include the liquid carriers exemplified above. Examples of the propellant include chlorofluorocarbons and liquefied natural gas.

[0026] The microbial control composition of the present invention may contain various additives as needed depending on the type of formulation, such as stabilizers such as antioxidants and ultraviolet absorbers; binders; resins with film-forming ability; emulsifiers, dispersants, spreading agents, wetting agents, penetrating agents; thickeners; flow aids; anti-caking agents; flocculants; ultraviolet scattering agents; moisture removers; and colorants.

[0027] Examples of antioxidants include phenolic antioxidants such as 4,4'-thiobis-6-t-butyl-3-methylphenol, butylated hydroxyanisole (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), p-octylphenol, mono(or di- or tri)-(α-methylbenzyl)phenol, 2,6-di-t-butyl-p-cresol (BHT), and pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)]propionate; amine antioxidants such as N,N'-di-2-naphthyl-p-phenylenediamine; hydroquinoline antioxidants such as 2,5-di(t-amyl)hydroquinoline; sulfur antioxidants such as dilaurylthiodipropionate; and phosphorus antioxidants such as triphenyl phosphite. Examples of ultraviolet absorbers include benzotriazole compounds such as 2-(2'-hydroxy-5'-methylphenyl)benzotriazole and 2-(2'-hydroxy-4'-n-octoxyphenyl)benzotriazole; benzophenone compounds such as 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-n-octoxybenzophenone; salicylic acid compounds such as phenyl salicylate and pt-butylphenyl salicylate; 2-cyano-3,3-diphenylacrylate 2-ethylhexyl, 2-ethoxy-2'-ethyloxalic acid bisanilide, and dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate. Examples of binders include sodium carboxymethylcellulose, methylcellulose, ethylcellulose, hydroxymethylcellulose, dextrin, pregelatinized starch, polyvinyl alcohol, polyvinylpyrrolidone, sodium lignosulfonate, and potassium lignosulfonate. Examples of resins capable of forming a coating include thermoplastic resins such as polyolefins such as polyethylene and polypropylene, polyvinyl acetate, polyvinyl alcohol, acrylic resins, polyvinyl chloride, styrene-based resins, fluororesins, chlorinated polyolefins, alkyd resins, polyamides, and polyesters; and thermosetting resins such as phenolic resins, urea resins, melamine resins, furan resins, unsaturated polyester resins, and epoxy resins. These resins may be in any form, such as solvent-based or emulsion-based.

[0028] As the emulsifier, dispersant, spreading agent, wetting agent, and penetrant, conventional surfactants such as anionic surfactants and nonionic surfactants can be used. Examples of anionic surfactants include metal soaps, sulfate ester salts such as sodium alkyl sulfate, alkylbenzenesulfonates such as sodium alkylbenzenesulfonate, alkylnaphthalenesulfonates such as sodium alkylnaphthalenesulfonate (e.g., manufactured by Takemoto Yushi Co., Ltd., trade name Newcalgen BX-C), 2-sulfosuccinate dialkyl salts such as sodium 2-sulfosuccinate dialkylsodium (e.g., manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name Neocol SW-C), polycarboxylic acid surfactants (e.g., manufactured by Sanyo Chemical Industries, Ltd., trade name Toxanon GR-30), α-olefin sulfonates, and polyoxyethylene distyrenated phenyl ether. Examples of suitable surfactants include ammonium sulfate (e.g., Dixsol 60A, product name, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), sodium lignin sulfonate, and potassium lignin sulfonate. Examples of suitable nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers (e.g., Noigen (EA-142), product name, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), polyoxyethylene aryl ethers, fatty acid polyhydric alcohol esters, fatty acid polyhydric alcohol polyoxyethylenes, sucrose fatty acid esters, and block copolymers of ethylene oxide and propylene oxide (e.g., Newpol PE-64, product name, manufactured by Sanyo Chemical Industries, Ltd.). Examples of thickeners include polyvinyl alcohol and polyacrylic acid and its salts. Examples of flow aids include organic lubricants such as PAP aids (e.g., isopropyl phosphate), wax, polyethylene, fatty acid metal salts, paraffin, and silicone oil, and inorganic lubricants such as talc. Examples of anti-caking agents include white carbon, diatomaceous earth, magnesium stearate, aluminum oxide, and titanium dioxide. Examples of flocculants include liquid paraffin, ethylene glycol, diethylene glycol, triethylene glycol, and isobutylene polymers (e.g., IP Solvent-2835, manufactured by Idemitsu Kosan Co., Ltd.). Examples of ultraviolet scattering agents include titanium dioxide. Examples of moisture removers include desiccants such as anhydrous gypsum and silica gel powder. Examples of colorants include organic or inorganic pigments and dyes.

[0029] Furthermore, the microbial control composition of the present invention may contain known antiseptics, antifungals, insecticides, pest repellents, insect growth regulators, and efficacy enhancers.

[0030] The microorganism control composition of the present invention is effective against any of bacteria, fungi such as molds, yeasts and wood-rotting fungi, and algae, and is preferably effective against bacteria. Bacteria include, but are not limited to, gram-negative bacteria and gram-positive bacteria. Examples of gram-negative bacteria include Escherichia and Pseudomonas. (genus Pseudomonas), genus Burkholderia (genus Burkholderia), genus Serratia (genus Serratia) ), Klebsiella genus, Legionella genus, Salmonella genus, Enterobacter genus, Proteus genus Examples of bacteria include those of the genus Branhamella. Examples of Gram-positive bacteria include Staphylococcus, Streptococcus, Bacillus, and Clostridium. Examples of bacteria that can be isolated include bacteria of the genus Clostridium, Enterococcus, Listeria, and Corynebacterium.

[0031] Examples of mold include zygomycetes such as those of the genus Absidia, Mucor, and Rhizopus, and those of the genus Chaetomium, Eurotium, Neurospora, and Saccharomyces. Any Ascomycetes, such as Acremonium, Alternaria, Aspergillus, Aureobasidium, Cladosporium, Fusarium, Penicillium, Phoma, Trichoderma, Rhodotorula, Candida, Trichophyton, and other imperfect fungi. Examples include: Examples of yeast include the genus Schizosaccharomyces, Protomyces Protoascomycetes such as the genera Protomyces and Taphrina; Euascomycetes such as the genus Endomyces; Hemiascomycetes such as the genus Saccharomyces; Imperfect ascomycete yeasts such as the genus Candida; and the genus Filobasidiella. Heterobasidiomycetes such as Rhodotorula and Trichosporon basidiomycete yeasts such as the genera Rhodosporidium, Sporidiobolus, and Xanthophyllomyces Examples include basidiomycete yeasts such as those of the genus Xanthophyllomyces. Examples of wood-decaying fungi include the genus Coniophora, the genus Trametes, the genus Postia, the genus Poria, the genus Gloeophyllum, the genus Lentinus, the genus Paxillus, the genus Fomitopsis, the genus Pleurotus, the genus Donkioporia, the genus Cell Genus Serpula, Glenospora, Perenniporia Examples include basidiomycetes such as the genus Antrodia. Algae are plants that live in water or on land, have assimilated pigments, and live independently, including, for example, cyanobacteria, glaucophytes, red algae, xanthophytes, yellow-green algae, green algae, diatoms, brown algae, dinoflagellates, green algae, brown algae, green zooxanthellae, charophytes, etc. The microbial control composition of the present invention exhibits excellent algae control effects, particularly in controlling cyanobacteria and green algae. Examples of cyanobacteria include the genera Oscillatoria and Phormidium, and examples of green algae include the genera Chlamydomonas, Chlorococcum, Chlorella, Desmodesmus, Klebsormidium, Trebouxiophyceae, and Ulothrix.

[0032] The microorganism control composition of the present invention is suitable for use as an industrial microorganism control composition or as a microorganism control composition for sanitary products to impart antibacterial properties to sanitary materials. It can also be suitably used to impart antibacterial properties to textile products (e.g., curtains, mats, felt, cushions, chairs, shoe insoles, clothing, shoes, hats), building materials (e.g., wallpaper, flooring, ceiling materials, handrails), pet products (e.g., pet sheets, pet toilets, cat litter, pet mats and carpets, pet beds, pet cages and houses, straw, deodorizing sprays, pet detergents, pet dishes, grooming supplies, trimming supplies, carrier bags, cat towers, pet toys, water treatment agents for aquatic organisms), and household products (e.g., toiletry products, detergents and finishing agents (fabric softeners), air fresheners, deodorizers, and deodorizers (standing, spray, and atomizing types), household goods, and the like). On the other hand, the microorganism control composition of the present invention does not include use as a pharmaceutical agent for internal administration by mammals such as humans, or agricultural and horticultural applications for application to cultivated plants. When used in industrial applications, the microbial control composition of the present invention can be effectively used to impart antibacterial properties to various industrial products, such as various industrial waters used in paper and pulp factories, cooling water circulation processes, etc., metalworking oils such as cutting oil, coated paper, paper coating solutions, paints, adhesives, casein, starch paste, glue, binders, synthetic rubber latex, resin emulsions, inks, polyvinyl alcohol films, vinyl chloride films, plastic products, cement admixtures, sealants, joint fillers, deodorizers, fibers, leather products, wood products, wood materials, paper products, filters, etc. More specifically, it is useful as a slime control agent in paper and pulp factories and cooling water circulation processes, etc., an antibacterial and antifungal agent for paper products, resin products, etc., and an antibacterial agent for paints, synthetic rubber latex, resins, inks, silicone sealants, etc. When the microbial control composition of the present invention is used in industrial applications, the amount added can be selected appropriately depending on the target of application, the type of microorganism to be controlled (bacteria, molds, yeasts, algae, etc.), and the control period. For example, when used as a slime control agent, the total amount of the antibacterial ingredients (a) and (b) per 1 kg of product should be 0.01 mg to 50,000 mg, preferably 0.5 mg to 10,000 mg; when used as a preservative, the total amount of the antibacterial ingredients (a) and (b) per 1 kg of product should be 0.01 mg to 50,000 mg, preferably 0.5 mg to 10,000 mg; and when used as an antifungal / yeast agent or antialgae agent, the total amount of the antibacterial ingredients (a) and (b) per 1 kg of product should be 0.01 mg to 100,000 mg, preferably 0.05 mg to 50,000 mg.

[0033] When used in hygiene product applications, the microbial control composition of the present invention can be effectively used to impart antibacterial properties to various hygiene products, such as paper, fibers, nonwoven fabrics, water-absorbent polymers, plastics, etc., by adding the microbial control composition of the present invention to such products as disposable diapers, textile products such as clothing, and pet litter boxes such as mats, pet sheets, and cat litter. In particular, the microbial control composition of the present invention exhibits excellent deodorizing effects in addition to excellent antibacterial activity, and is therefore suitable for use in these hygiene products, as it can suppress unpleasant odors. When the microorganism control composition of the present invention is used in hygiene products, the amount added can be selected appropriately depending on the object and purpose of application. For example, when used in disposable diapers, the total amount of the antibacterial components (a) and (b) per product is 1 mg to 10,000 mg, preferably 10 mg to 5,000 mg; when used in textile products, the total amount of the antibacterial components (a) and (b) per kg of product is 10 mg to 50,000 mg, preferably 50 mg to 10,000 mg; when used in pet sheets, the total amount of the antibacterial components (a) and (b) per product is 1 mg to 10,000 mg, preferably 10 mg to 5,000 mg; and when used in pet toilets, the total amount of the antibacterial components (a) and (b) per product is 10 mg to 100,000 mg, preferably 50 mg to 50,000 mg. [Example]

[0034] The present invention will be explained in more detail below by way of test examples, but the present invention is not limited to these examples. Test examples demonstrate that the microorganism control composition of the present invention has antibacterial activity.

[0035] <Antibacterial Evaluation 1: Ingredient (a) Norfloxacin> (1) Test specimen Example 1 Component (a) norfloxacin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 1 part by weight and component (b) zeolite with a SiO2 / Al2O3 (molar ratio) of 100 (manufactured by Mizusawa Industrial Chemicals, Ltd., Silton MT-100) 99 parts by weight were mixed in a mortar for 1 minute, and 100 mg of this mixture was dispersed in 10 mL of sterilized water to obtain the test specimen of Example 1. <Example 2, Comparative Examples 1 and 2> In Example 2 and Comparative Examples 1 and 2, test samples were prepared in the same manner as in Example 1 by dispersing the components (a) and (b) in 10 mL of sterilized water so as to achieve the contents shown in Table 1. The contents of component (a) and component (b) in the test samples of Examples 1 and 2 and Comparative Examples 1 and 2 are shown in Table 1.

[0036] [Table 1]

[0037] (2) Antibacterial (antibacterial) testing method The above test samples were each added to glucose broth medium (pH 6.0), and then a bacterial suspension containing the following bacteria was inoculated using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.) and cultured at 33°C for 1 day. The growth of the bacteria after culture was then observed, and the minimum inhibitory concentration (MIC: μg / mL) was calculated for each. Bacillus subtilis Pseudomonas aeruginosa Serratia marcescens Table 2 shows the minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Examples 1 and 2 and Comparative Examples 1 and 2 against the above three bacteria.

[0038] [Table 2]

[0039] As shown in Table 2, Comparative Example 2, which contains only zeolite with a SiO2 / Al2O3 (molar ratio) of 100, which is component (b) of the present invention, shows no antibacterial effect. However, it was confirmed that the microorganism control compositions of Examples 1 and 2, which contain a combination of component (a) and component (b) of the present invention, have significantly reduced minimum inhibitory concentrations (MIC) (μg / mL) against bacteria compared to Comparative Example 1, which contains only component (a) of the present invention. In other words, it has been confirmed that the microbial control composition of the present invention, by combining norfloxacin, a quinolone compound represented by the above general formula (1) as component (a), with zeolite having an SiO2 / Al2O3 (molar ratio) of 100 as component (b), greatly improves the antibacterial activity of component (a) alone, even though component (b) does not exhibit any antibacterial activity, thereby achieving an extremely excellent activation effect of component (a) that far exceeds expectations.

[0040] <Antibacterial Evaluation 2: Component (a) Ofloxacin> Test specimens of Example 3 and Comparative Example 3 were prepared in the same manner as in Example 2 and Comparative Example 1 in the above "Evaluation of antibacterial activity 1," except that component (a) norfloxacin was replaced with ofloxacin. The minimum inhibitory concentrations (MIC: μg / mL) of the test specimens of Example 3 and Comparative Example 3 against Bacillus subtilis, Pseudomonas aeruginosa, and Serratia marcescens were calculated in the same manner as in the "Test method for antibacterial activity (antibacterial activity)." The minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Example 3 and Comparative Examples 2 and 3 against the above bacteria are shown in Table 3.

[0041] [Table 3]

[0042] <Antibacterial Evaluation 3: Component (a) Oxolinic Acid> Test specimens of Example 4 and Comparative Example 4 were prepared in the same manner as in Example 2 and Comparative Example 1 in the above "Evaluation of antibacterial activity 1," except that component (a) norfloxacin was replaced with oxolinic acid. The minimum inhibitory concentrations (MIC: μg / mL) of the test specimens of Example 4 and Comparative Example 4 against Bacillus subtilis and Serratia marcescens were calculated in the same manner as in the "Test method for antibacterial activity (antibacterial activity)." The minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Example 4 and Comparative Examples 2 and 4 against the above bacteria are shown in Table 4.

[0043] [Table 4]

[0044] <Antibacterial Evaluation 4: Component (a) Nalidixic Acid> Test specimens of Example 5 and Comparative Example 5 were prepared in the same manner as in Example 2 and Comparative Example 1 in the above "Evaluation of antibacterial activity 1," except that component (a) norfloxacin was replaced with nalidixic acid. The minimum inhibitory concentrations (MIC: μg / mL) of the test specimens of Example 5 and Comparative Example 5 against Bacillus subtilis and Serratia marcescens were calculated in the same manner as in the "Test method for antibacterial activity (antibacterial activity)." Table 5 shows the minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Example 5 and Comparative Examples 2 and 5 against the above bacteria.

[0045] [Table 5]

[0046] <Antibacterial Evaluation 5: Component (a) Piromidic Acid> Test specimens of Example 6 and Comparative Example 6 were prepared in the same manner as in Example 2 and Comparative Example 1 in the above "Evaluation of antibacterial activity 1," except that component (a) norfloxacin was replaced with piromidic acid. The minimum inhibitory concentrations (MIC: μg / mL) of the test specimens of Example 6 and Comparative Example 6 against Bacillus subtilis were calculated in the same manner as in the "Test method for antibacterial activity (antibacterial activity)." Table 6 shows the minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Example 6 and Comparative Examples 2 and 6 against the above bacteria.

[0047] [Table 6]

[0048] As shown in Tables 3 to 6, it was confirmed that the microbial control compositions of Examples 3 to 6, which use a combination of component (a) and component (b) of the present invention, have significantly reduced minimum inhibitory concentrations (MIC) (μg / mL) against bacteria compared to Comparative Examples 3 to 6, which contain only component (a) of the present invention. In other words, the microbial control composition of the present invention is a quinolone compound represented by the above general formula (1) of which component (a) is one of ofloxacin, oxolinic acid, nalidixic acid, or piromidic acid, combined with a zeolite having an SiO2 / Al2O3 (molar ratio) of 100 as component (b). This significantly improves the antibacterial activity of component (a) alone, even though component (b) does not exhibit any antibacterial activity. In other words, it has been confirmed that this composition exhibits an extremely excellent activation effect of component (a) that far exceeds expectations.

[0049] <Evaluation of antibacterial properties 6: Verification of the SiO2 / Al2O3 (molar ratio) of component (b)> Test specimens of Examples 7 to 9 and Comparative Example 7 were prepared in the same manner as in Example 2 of the above "Evaluation of Antibacterial Activity 1," except that the zeolite with an SiO2 / Al2O3 (molar ratio) of 100 (Shilton MT-100, manufactured by Mizusawa Industrial Chemicals, Ltd.) was replaced with zeolites with an SiO2 / Al2O3 (molar ratio) of 3.8 (Comparative Example 7), 30 (Example 7), 400 (Example 8), or >2000 (Example 9). The minimum inhibitory concentrations (MIC: μg / mL) of the test specimens of Examples 7 to 9 and Comparative Example 7 against Bacillus subtilis, Pseudomonas aeruginosa, Serratia marcescens, and Staphylococcus aureus were calculated in the same manner as in the "Test method for antibacterial activity (antibacterial activity)." The zeolites used were all the following products manufactured by Mizusawa Industrial Chemicals, Ltd. Comparative Example 7: Mizuka Sieves Y-400: SiO2 / Al2O3 (molar ratio): 3.8 Example 7: Mizuka Sieves EX-122: SiO / AlO (molar ratio): 30 Example 8: Silton MT-400: SiO / AlO (molar ratio): 400 Example 9: Silton MT-8000: SiO / AlO (molar ratio): >2000 Table 7 shows the minimum inhibitory concentrations (MIC: μg / mL) of the test samples of Examples 7 to 9 and Comparative Example 7 against the above bacteria, as well as the results of Example 2 in the above "Antibacterial Evaluation 1," and the minimum inhibitory concentrations (MIC: μg / mL) against Staphylococcus aureus. Test samples were prepared in the same manner as in Comparative Example 2 of "Evaluation of Antibacterial Activity 1" above, except that the zeolite with a SiO2 / Al2O3 (molar ratio) of 100 (Shilton MT-100, manufactured by Mizusawa Industrial Chemicals, Ltd.) was replaced with zeolites with SiO2 / Al2O3 (molar ratios) of 3.8, 30, 400, and >2000.The minimum inhibitory concentrations (MIC: μg / mL) against Bacillus subtilis, Pseudomonas aeruginosa, Serratia marcescens, and Staphylococcus aureus were calculated, and all were found to be >10,000.It was also confirmed that the minimum inhibitory concentration (MIC: μg / mL) against Staphylococcus aureus of the test sample of Comparative Example 2 was also >10,000.

[0050] [Table 7]

[0051] As shown in Table 7, it was confirmed that the microorganism control compositions of Examples 2 and 7 to 9, which contain component (b) of the present invention, i.e., a zeolite with an SiO2 / Al2O3 (molar ratio) of 10 or more, have significantly reduced minimum inhibitory concentrations (MIC) (μg / mL) against bacteria compared to the microorganism control composition of Comparative Example 7, which contains a zeolite with an SiO2 / Al2O3 (molar ratio) of less than 10. In other words, it has been revealed that the microorganism control composition of the present invention employs a zeolite with an SiO2 / Al2O3 (molar ratio) of 10 or more as component (b), and by using it in combination with component (a), it exhibits a remarkable effect of significantly improving antibacterial activity to a level that cannot be achieved by component (a) alone. The microorganism control compositions of the present invention exhibit excellent deodorizing effects in addition to the excellent microorganism control activity described above, and Examples 1 to 9 have a superior deodorizing effect compared to Comparative Example 7. [Industrial Applicability]

[0052] The microbial control composition of the present invention exhibits excellent antibacterial activity and can be applied to various industrial products and industrial materials, and can exhibit excellent antibacterial activity by simply adding a small amount as an additive that exhibits antibacterial activity. Furthermore, the microorganism control composition of the present invention exhibits excellent deodorizing effect in addition to excellent antibacterial activity, and is therefore suitable for use in sanitary products such as disposable diapers to suppress unpleasant odors.

Claims

1. A microorganism control composition comprising the following component (a) and the following component (b), wherein the weight ratio of the component (a) to the component (b) is within the range of 0.1:99.9 to 20:80: Component (a): One or more selected from enoxacin, tosufloxacin, oxolinic acid, nalidixic acid, norfloxacin, sarafloxacin, difloxacin, fleroxacin, lomefloxacin, enrofloxacin, ciprofloxacin, gatifloxacin, sparfloxacin, danofloxacin, moxifloxacin, garenoxacin, sitafloxacin, orbifloxacin, nadifloxacin, ofloxacin, levofloxacin, pazufloxacin, marbofloxacin, piromidic acid, pipemidic acid, and salts thereof. Component (b): SiO ２ / Al ２ O ３ Zeolite with a molar ratio of 10 or more

2. 2. The microorganism control composition according to claim 1, wherein the component (a) is one or more selected from the group consisting of oxolinic acid, nalidixic acid, norfloxacin, ofloxacin, piromidic acid, and salts thereof.

3. 3. The microorganism control composition according to claim 1, wherein the zeolite is an MFI type zeolite.

4. A product containing the microbial control composition according to any one of claims 1 to 3.

5. A method for producing a microorganism control material by applying the microorganism control composition according to any one of claims 1 to 3 to a material.

Images