WO2005063019A1 - Antimicrobial agent - Google Patents

Abstract

An antimicrobial agent comprising 7,8-dihydrokawain as an active ingredient, which antimicrobial agent is capable of controlling or preventing bacteria such as those of the genera Bacillus, Escherichia and Pseudomonas, yeasts such as those of the genera Saccharomyces and Rhodotorula, molds such as those of the genera Alternaria, Cladosporium, Fusarium and Eurotium, etc. The above 7,8-dihydrokawain may be obtained from an organic solvent extract of a plant belonging to the species Piper methysticum or a matter resulting from treatment thereof. This antimicrobial agent exerts high controlling capability, being highly safe to human and livestock, and does not have hazardous impact on environment.

Description

 Specification

 Antimicrobial agent

 Technical field

 [0001] The present invention relates to microorganisms having high safety (for example, in various buildings such as dwellings, stores, factories, warehouses, and hospitals, in various vehicles such as vehicles, ships, and aircraft, in fibers, leather, paints, and adhesives). Chemicals such as chemicals, plastics and metalworking oils, bioactive products such as pharmaceuticals and agricultural chemicals, microorganisms capable of reproducing in cosmetics, foods, etc.).

 Background art

 [0002] In recent years, with the airtightness of a building, the inside of the building tends to be in a high humidity environment suitable for propagation of microorganisms. For example, the propagation of bacteria and the like may cause harm to the human body as a pathogenic bacterium. In addition, microorganisms such as molds not only contaminate the aesthetics of the dwelling, but their spores can cause allergic bronchitis and asthma. In addition, since microorganisms such as molds also serve as nutrients such as mites, they indirectly cause atopic dermatitis. Also, among microorganisms such as yeast, for example, yeast belonging to the genus Rhodotorula contaminates bathrooms and the like in red and black. Microorganisms such as molds belonging to the genus Eurotium can grow in the air and in dry foods, and can also grow in a dry environment.

 [0003] Furthermore, microorganisms inhabit a very wide area and degrade various articles. Biological degradation of articles by microorganisms is not limited to the building and components of various transport vehicles (vehicles, ships, aircraft, etc.), and various articles such as natural products (leather, etc.), chemical products (synthetic fibers, It also occurs in synthetic leather, plastics, paints, adhesives, metalworking oils, etc., metals (iron, aluminum, etc.) products, bioactive products (pharmaceuticals, pesticides, etc.), foods and cosmetics.

[0004] To prevent erosion of buildings and articles by such microorganisms, antimicrobial agents such as germicides containing various compounds as effective components have been used. High safety against microorganisms and high control over microorganisms [0005] Japanese Patent Application Laid-Open No. 2003-252708 (Patent Document 1) discloses a wood preservative containing a compound such as power wine, yangonine, or methistin as an active ingredient. It is described as useful for preventing wood damage, wood decay by wood decay fungi, and wood contamination by wood contaminants. Further, in this document, 7,8-dihydrokine is exemplified together with a power wine, a 5,6-dehydropower wine, and the like. Further, in the examples of this reference, four wood contaminants (Aspergillus niger, Penicillium foniculosum, Aureobasidiumu pullulans, and A high concentration of 7,8-dihydro wine (50000 gZml) was applied to the mixed spores of Gliocladium virens], and no bacterial growth was observed by the third day after application. It is described that you have tried.

 [0006] Further, Japanese Patent No. 3306054 (Patent Document 2) is characterized in that it contains, as an active ingredient, an exudate of a plant belonging to moss species (Piper methysticum) or a treated product thereof, or a treated product thereof. Wood preservatives for fungicidal wood are disclosed. In the examples of this document, a high-concentration acetone or methanol extract (125000 μg / ml) of the above-ground stem of moss (Piper methysticum) was used against the mixed spores of the four wood-contaminating bacteria described in Patent Document 1. It was described that mold growth was observed only on the side of the test sample when the test was applied.

 [0007] Furthermore, Japanese Patent Application Laid-Open No. 2003-267802 (Patent Document 3) discloses that

 A wood preservative which is an antifungal agent for wood containing leaves of a plant belonging to Methysticum) or a processed product thereof as an active ingredient is disclosed. In the example of this document, a high-concentration acetone extract (125000 μg / ml) of mosquito (Piper methysticum) leaves was also used against mixed spores of the above four types of wood-contaminating bacteria described in Patent Document 1. When applied, it is stated that mold growth was observed only on the side of the specimen.

 [0008] However, no more effective control method has been found for bacteria, yeasts and specific molds.

 Patent Document 1: Japanese Patent Application Laid-Open No. 2003-252708 (Claims, Paragraph Number [0003]) Patent Document 2: Patent No. 3306054 (Claims, Paragraph Number [0032] — [0036]) Patent Documents 3: JP 2003-267802 A (Claims, paragraph number [0031] —

[0037]) Disclosure of the invention

 Problems to be solved by the invention

 [0009] Accordingly, an object of the present invention is to provide an antimicrobial agent which has high safety and high controllability against specific microorganisms, and a method for controlling microorganisms using the same.

[0010] Another object of the present invention is to provide an antimicrobial agent capable of effectively controlling microorganisms contaminating a living environment that not only adversely affect humans and livestock, but also to be used in a highly airtight living environment, and to use the same. It is an object of the present invention to provide a method for controlling microorganisms.

 [0011] Still another object of the present invention is to provide an antimicrobial agent capable of controlling microorganisms simply and with high efficiency, and a method for controlling microorganisms using the same.

 Means for solving the problem

 The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that they have a strong inhibitory activity on a specific microorganism, and have completed the present invention.

 [0013] That is, the present invention discloses the following antimicrobial agents.

 [0014] (A) An antimicrobial agent containing 7,8-dihydro wine as an active ingredient, for controlling or preventing at least one microorganism selected from the group consisting of (1) and (3) also having strength.

[0015] (1) bacteria,

 (2) yeasts,

 (3) Molds belonging to at least one genus selected from the genus Alternaria, the genus Cladosporium, the genus Fusarium, and the genus Eurotium

 The present invention also discloses the following antimicrobial agents.

(B) The antimicrobial agent according to (A), wherein the bacterium is at least one selected from the genus Bacillus, the genus Escherichia, and the genus Pseudomonas.

 (C) The antimicrobial agent according to (A), wherein the yeast is at least one selected from the genus Saccharomyces and the genus Rhodotorula.

[0018] (D) Molds of Cladosporium cladosporioides , Eurotium tonophilum, Alternaria 'SP (

(A), which is at least one selected from Alternaria sp. And Fusarium sp.

[0019] (E) The antimicrobial agent according to the above (A), which contains 7,8-dihydropower wine contained in an organic solvent extract of a plant belonging to the species of Piper methysticum or a processed product thereof.

[0020] (F) A defatted plant of a plant belonging to the species of Piper methysticum or a processed product thereof was extracted with at least one extraction solvent selected from alcohols, esters, and ketones. The antimicrobial agent according to the above (A), comprising 7,8-dihydro power wine contained in the extract.

 [0021] The present invention further includes a method for controlling or preventing the following microorganisms.

(G) A method for controlling or preventing microorganisms by applying the antimicrobial agent according to the above (A) to an object to be treated (or an area to be treated) in which microorganisms can grow or propagate.

(H) The method according to (G) above, wherein the antimicrobial agent is applied to a growth or propagation area of a microorganism.

 The invention's effect

 [0024] Since the antimicrobial agent of the present invention contains 7,8-dihydropowered wine present in natural plants, it has high safety and high controllability against specific microorganisms. In addition, even when used in a highly airtight living environment, microorganisms that contaminate the living environment without adversely affecting humans and animals can be effectively controlled. Further, in the present invention, microorganisms can be controlled or prevented simply and efficiently.

 Detailed description of the invention

[0025] [Antimicrobial agent]

 The antimicrobial agent contains 7,8-dihydro wine as an active ingredient. (1) Bacteria, (2) Enzymes, and (3) Genus Alternaria, Cladosporium, Fusarium Microorganisms such as molds belonging to the genera (Fusarium) and Eurotium can be effectively controlled or prevented.

[0026] (7, 8-dihydropower wine)

Plants rich in 7,8-dihydro-powered wines include plants belonging to the species Pipper methysticum. The plant belonging to the species Kapi (Piper methysticum) is Newgear It grows in the Polynesian Islands, etc., and includes wild species (Piper wichmannii) in addition to mosquito species (Piper methysticum). Plants belonging to the mosquito species (Piper methysticum) are large herbs with a height of 2 to 3 m. In the Polynesian Islands, for example, their roots are crushed and squeezed, and dried roots are crushed and extracted with water. There is a custom of drinking soup as a luxury item. Kaji (Piper methysticum) is sometimes called Likva, Likwaka ヮ, Likvakava, Yangona, Shakao, etc., depending on the region.

 [0027] The 7,8-dihydro wine is present both above and below the plant of the species belonging to the genus Piper methysticum. For example, the above-ground parts include stems (stems, branches, rinds, stems, etc.), leaves (leaves, petiole, etc.), flowers (flowers, bracts, stalks, florals, etc.), seeds (fruits, etc.) , Seeds, temporary seed coat, pericarp, etc.), and the underground part includes a root part (root, root bark, etc.) and a rhizome part (rhizome or rhizome, etc.). These sites can be used alone or in combination of two or more. Of these parts, 7,8-dihydro wines are more abundant in above-ground parts (for example, stems).

 [0028] In addition, 7,8-dihydro wines have low solubility in water, and therefore cannot be efficiently extracted with water. For this reason, 7,8-dihydro power wines are often obtained by extracting with plants belonging to the species of mosquitoes (Piper methysticum) or by treating them with organic solvents.

 [0029] Examples of the processed product include shreds, dried products, pulverized products, extracts, exudates, and the like. The treated product can be obtained by subjecting the plant body to processing such as shredding, drying, pulverizing, extracting, and exuding (including the extraction of exudate from the plant). Drying, shredding, grinding, extracting, and exuding) can be used alone or in combination of two or more. The exudate also includes substances separated and exuded in the cutting, drying, pulverizing processes, etc., using only exudates of plant vitality.

[0030] Examples of the extraction solvent for the plant or its processed product include alcohols (eg, methanol, ethanol, _n -propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, monohydric alcohols such as n-octanol, 2-butyloctanol, lauryl alcohol, cyclohexanol; dihydric or polyhydric alcohols such as glycerin, ethylene glycol, propylene glycol, etc.); ethers [for example, Chain ethers (eg, ethyl ether, propyl ether, isopropyl ether , Dimethoxyethane, etc.), cyclic ethers (eg, dioxane, tetrahydrofuran, etc.), mono- or dialkylene glycol monoalkyl ethers (eg, cellosolves such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), diethylene glycol monoethyl ether Ketones (eg, acetone, methylethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.); esters (eg, acetates such as ethyl acetate, butyl acetate, etc.); Adipic esters such as dihexyl adipate, dioctyl adipate, diisonol adipate (DINA), and didecyl adipate; esters of citrate such as acetyl triethyl citrate and acetyl tributyl atenate Halogenated hydrocarbons (eg, carbon tetrachloride, chlorohonolem, dichloromethane, 1,2-dichloroethane, etc.), aliphatic hydrocarbons (eg, hexane, octane, etc.); Alicyclic hydrocarbons (eg, cyclohexane, cycloheptane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, etc.); -tolyls (eg, acetonitrile, benzo-tolyl, etc.); Acids (formic acid, acetic acid, etc.); aprotic polar solvents (eg, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, pyridine and the like). These solvents can be used alone or in combination of two or more.

 [0031] Further, the 7,8-dihydro-powered wine may be obtained by defatting a plant belonging to moss species (Piper methysticum) or a processed product thereof, and extracting the defatted product. By degreasing, impurities can be removed and high-purity 7,8-dihydro wines can be extracted. Examples of the solvent used in the degreasing treatment include the aliphatic hydrocarbons and alicyclic hydrocarbons described above. These degreasing solvents can be used alone or in combination of two or more. Among these degreasing solvents, aliphatic hydrocarbons (for example, hexane) are preferred.

[0032] Among the extraction solvents, alcohols (for example, monohydric alcohols having about 114 carbon atoms such as methanol, ethanol and i-propanol; dihydric alcohols such as ethylene glycol and propylene glycol), esters ( For example, ethyl acetate, butyl acetate, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.) are preferred. Particularly, methanol, ethanol, i-propanol, propylene glycol, Acetone and the like are preferred. [0033] The amount of the solvent used in the degreasing treatment is 200-10000 parts by weight, preferably <300-5000 parts by weight, and more preferably <500-2000 parts by weight, based on 100 parts by weight of the plant to be extracted. It is about. The extraction solvent may be used within a range that does not impair the extraction efficiency and the extraction operation. For example, 100 to 10,000 parts by weight, preferably 200 to 5000 parts by weight, per 100 parts by weight of the plant to be extracted. And more preferably about 300 to 2000 parts by weight. The degreasing temperature and the extraction temperature are, for example, about 0 to 150 ° C, preferably about room temperature (for example, 15 to 25 ° C) to about 120 ° C.

 [0034] The 7,8-dihydropower wine contained in the antimicrobial agent may be a pure product or a mixture. For example, a pure 7,8-dihydro wine can be synthesized by a method known in the literature (Acta Chemica Scandinavica B 30, 7: 613-678, 1976; Planta Med., 64: 504, 1998). As the 7,8-dihydro wine, it is preferable to use an extract from a plant rich in 7,8-dihydro wine.

 [0035] The formulation of the antimicrobial agent used in the present invention is not particularly limited as long as it contains 7,8-dihydro wine, and examples of the formulation include a solution, a wettable powder, a water solvent, and a suspension. Suspensions, dispersants, emulsions, oils, lotions, coatings, sprays, aerosols and other liquids; pastes, creams and other semi-solids; powders, granules, microcapsules, microspheres, flowables Solidifying agents such as foaming agents, solidifying agents (compressed solidifying agents obtained by compressing powders and Z or granules, solidifying agents obtained by solidifying a fluid formulation with a cooling or coagulating agent, etc.) Is mentioned. These formulation forms can be appropriately selected according to the purpose of use and the site of application. These preparations can be manufactured by a conventional method.

 [0036] The liquid preparation and semisolid preparation can be produced, for example, by diluting the extract or exudate with a suitable liquid diluent or carrier. In the case of a wettable powder, a solid diluent or a carrier may be further used. In the case of aerosols, liquefied gas (fluorinated hydrocarbons, hydrocarbons, liquefied petroleum gas, dimethyl ether, etc.), compressed gas (inert gas such as nitrogen gas, dioxide carbon, etc.) It can be produced by appropriately using a propellant such as

[0037] Examples of the liquid diluent or carrier include water, a plasticizer (for example, an ester plasticizer such as di-2-ethylhexyl adipate) and kerosene in addition to the above-mentioned extraction solvents. Petroleum-based solvents: Aromatic coals such as ethyl naphthalene and phenyloxylethane Hydrogen hydride; phosphoric acid esters such as 2-ethylhexylphenyl phosphate may also be used. These liquid diluents and carriers can be used alone or in combination of two or more. Examples of the solid diluent or carrier include diatomaceous earth, mica, clay, kaolin, talc, quartz powder, bentonite, and the like. These solid diluents or carriers can also be used alone or as a mixture of two or more.

[0038] The solid agent can be produced, for example, by diluting or granulating the extract or exudate with an appropriate solid diluent or carrier. Examples of the solid diluent or carrier include, in addition to the solid diluents described above, talc such as talc powder and laurite powder, tares such as fine powder clay; mineral powders such as calcium carbonate; sulfur powder; urea powder Plant powders such as wood flour and starch; metal stones (such as fatty acid stones); and various carriers commonly used in residential preparations, agricultural chemicals or horticultural preparations. These solid diluents and carriers are often used as extenders. Solid diluents and carriers can be used alone or in combination of two or more.

 [0039] Among these dosage forms, liquid or semi-solid preparations are preferred in order to be efficiently applied to a site contaminated with microorganisms or a treated part, and particularly liquid preparations (for example, coating preparations, spray preparations, and aerosol preparations) are preferred. And the like). In the case of a spray or an aerosol, the liquid to be ejected may be in the form of a mist or a foam, but is preferably in the form of a foam because of its high adhesion to a contaminated site.

 [0040] The antimicrobial agent may be various additives depending on the type of the preparation, if necessary, for example, a stabilizer such as an antioxidant or an ultraviolet absorber; a binder; Emulsifiers, dispersants, spreading agents, wetting agents, penetrants; thickeners; flow aids; anti-caking agents; coagulants; ultraviolet scattering agents; Well.

Examples of the antioxidant include 4,4′-thiobis 6-t-butyl-3-methylphenol and butylated hydroxysol (a mixture of 2 t-butyl-4-methoxyphenol and 3 t-butyl-4-methoxyphenol) ), P-octylphenol, mono (or di- or tri-)-(0; -methylbenzyl) phenol, 2,6-di-tert-butyl-p-talesol (BHT), pentaerythrityltetrakis [3- (3,5 Phenolic antioxidants such as —di-tert-butyl-4-hydroxyphenyl)] propionate; N, N ′ —di-2-naphthyl-p-phenylene Amine antioxidants such as amines; hydroquinoline antioxidants such as 2,5-di (t-amyl) hydroquinoline; sulfur-based antioxidants such as dilaurylthiodipropionate; triphenylphosphites and the like. Examples thereof include phosphorus-based anti-dandruff agents.

 [0042] Examples of the ultraviolet absorbent include benzotriazole compounds such as 2- (2'-hydroxy-5'methylphenyl) benzotriazole and 2- (2'-hydroxy-4'notatoxyl) benzotriazole; Benzophenone-based compounds such as 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4n-otatooxybenzophenone; salicylic acid-based compounds such as salicylic acid phenol and p-t butylphenol salicylate; 2-ethyl Xyl 2-cyano-3,3-diphenyl acrylate, 2 ethoxy-2'-bisethyl oxalate, dimethyl succinate 1- (2-hydroxyethyl) 4-hydroxy-2,2,6,6-tetramethylbiperidine And condensates.

 Examples of the binder include carboxymethylcellulose sodium salt, methylcellulose, ethylcellulose, hydroxymethylcellulose, dextrin, pregelatinized starch, polybutyl alcohol, polybutylpyrrolidone, sodium lignosulfonate, and potassium ligninsulfonate. And the like.

 [0044] The resin having a film forming ability includes, for example, polyolefins such as polyethylene and polypropylene, polyacetate butyl, polybutyl alcohol, acrylic resin, polychlorinated butyl, styrene resin, fluorine resin, and chlorinated resin. Thermoplastic resins such as polyolefin, alkyd resin, polyamide, polyester; thermosetting resins such as phenol resin, urea resin, melamine resin, furan resin, unsaturated polyester resin, epoxy resin, etc. Can be exemplified.

As the emulsifier, dispersant, spreading agent, wetting agent, and penetrating agent, conventional surfactants such as an ionic surfactant and a nonionic surfactant can be used. Examples of the a-on type surfactant include metal stones, sulfates such as alkyl sodium sulfate, alkylbenzene sulfonates such as sodium alkylbenzene sulfonate, sodium alkylnaphthalene sulfonate [for example, Takemoto Oil and Fat ( Alkylnaphthalenesulfonates such as trade name-Eucalgen BX-C], and dialkyl sodium 2-sulfosuccinate [eg, Neocol SW-C trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.] Dialkyl sulfosuccinate, polycarboxylic acid type surfactant [for example, Toxa (trade name, manufactured by Sanyo Iridari Co., Ltd.) Non-GR-30], α-sulfuric acid sulfonic acid salt, polyoxyethylene distyrenated phenol ether sulfate ammonium salt [for example, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., trade name: Dixsol 60Α], Examples thereof include sodium lignesulfonate and potassium lignesulfonate. Noon-based surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether [for example, manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name: Inogen-J. ], Polyoxyethylene aryl ether, fatty acid polyhydric alcohol ester, fatty acid polyhydric alcohol polyoxyethylene, sucrose fatty acid ester, block copolymer of ethylene oxide and ethylene oxide propylene [for example, Sanyo-Daisei Co., Ltd., brand name New Pole ΡΕ-64].

Examples of the thickener include polybutyl alcohol, xanthan gum, polyacrylic acid and salts thereof, and the like. Examples of the flow aid include organic lubricants (eg, auxiliaries (eg, isopropyl phosphoric acid)), vitamins, petrolatum, polyethylene, fatty acid metal salts, paraffin, and silicone oil, and inorganic lubricants such as talc. Examples of the anti-caking agent include white carbon, diatomaceous earth, magnesium stearate, aluminum oxide, titanium dioxide and the like. Examples of the flocculant include liquid paraffin, ethylene glycol, jeti-lendlycol, triethylene glycol, and isobutylene polymer [for example, manufactured by Idemitsu Petrochemical Co., Ltd., trade name: IP Solvent-2835]. Examples of the ultraviolet scattering agent include titanium dioxide. Examples of the water removing agent include desiccants such as anhydrous gypsum and silica gel powder. Colorants include, for example, organic or inorganic pigments and dyes.

 Furthermore, the antimicrobial agent of the present invention may contain a compound having a known or commonly used antimicrobial action (antibacterial, antiseptic, or antifungal action) and the like.

[0048] Examples of the compound having an antimicrobial activity include, for example, 3 Promo 2,3 Jordo 2 propyl-rutyl carbonate, 3-Prodo 2 propyl butyl carbamate, 2,3,3-Toriodo arinorea Organic compounds such as norecone and parachlorophenylenole 3- 3-propanoreginolehonolemar; benzimidazole and benzothiazole such as 2- (4 thiazolyl) benzimidazole and 2-thiocyanomethylthiobenzozothiazole Compound; 1— (2— (2 ′, 4′—dichloromouth phenol) —1,3-dioxolan-2-ylmethyl) —1 Hl, 2, 4-triazole, 1-(2-(2 ', 4'-dichloromethyl)-4--propyl-1, 3-dioxolane-2-ylmethyl) 1H-1, 2, 4 triazole, α — (2 -— (4-chlorophenyl) ethyl) _—α (1,1-dimethylethyl) —1H—1,2,4-triazole-1 Ethanol and other triazole compounds; zinc bis— (2 —Pyridine-thiol 1-year-old oxide) Organozincs such as zinc phthalate; benzoic acids such as benzoic acid, sodium benzoate, paraoxybenzoic acid esters (parabens, for example, methylparaben, para-hydroxybenzoic acid η-butyl, etc.) 4 Natural compounds such as isopropyl troborone (hinokitiol) and borax, and didecyldimethylammonium-dum chloride. Examples of the compound having an antimicrobial action (for example, an antiseptic / antifungal agent) which is capable of being added to the above compound include compounds represented by the following formula (I).

[0049]

(Wherein, R ¹ and R ² are the same or different and each represents a C alkyl group or a C

 1-18 2-18

R ³ and R ⁴ are the same or different and represent a hydrogen atom, a hydroxyl group, an amino group, a C alkyl group or a C alkoxy group, and R ⁵ is a C alkylene group, a C alkyl group;

1-6 1-6 2-18 3-18 represents a rene group, a phenylene group or a xylylene group, wherein R ¹ — R ⁵ is a C alkyl group,

 1-6 1-6 Can be substituted with an alkoxy group, c alkoxy carboxy group or halogen

 1-6

Upsilon ¹ or, -NHCO-, -CONH-, -NHCS -, - COO- COS- O- Also I or one S- a, Υ ² ί Also, -CONH-, -NHCO-, -CSNH -, - OOC SOC Ο or ί indicates S—, and Ζ— indicates a turn on. ).

[0050] Examples of the halogen include chlorine, fluorine, bromine, and iodine. Examples of the union represented by Ζ— include a halogen ion (eg, Cl Br— and Γ) and a nitrate ion (NO— ), And, for example, acetate ion (CH 2 COO—), propionate ion (

3 3

Organic acid ions such as CH 2 COO—). Of these ars, inorganic On is preferred.

Such a bisquaternary ammonium salt conjugate can be produced by a known method according to the specific compounds shown below, and specific examples thereof include, for example, N, N'-hexamethylenebis (4 rubumoylu 1-decylpyridi-pembromide) (dimer 38, made of pine rice), N, N-hexamethylenebis (4-lbumbamoyl-1-decylpyridi-pumacetate) (dimer 38A, made of ynui), 4, 4 '(tetramethylene dicarbyl diamino) bis (1 decyl pyridi-dimethyl bromide) (Dimer 136, made by Iny), 4, 4, 1 (tetramethylenedicarbyl diamino di) bis (1 decyl pyridi-dimethyl acetate) (dimer) 136A, manufactured by Inui Corporation), 1,4-tetramethylene bis (4 rubamoyl 1-hexadecyl pyridi-dimethylbromide), 1,6-hexamethylene Bis (3-force rubamoyl-1-dodecylpyridi-dimethyl bromide), 1,6 Ottatamethylenebis (3-force rubamoyl-1-tetradecylpyridi-dimethyl bromide), 3,3,1- (1,3, tri) Methylenedicarbol-diamino) bis (1-dodecylpyridi-dimethylbromide), 4,4, (p-xylyldithio) bis (1 year old octylpyridyl-dimethyliodide), 3,3, — (m-xylyldithio) bis (1-tetra) Decylpyridi-pembromide), N, N,-(p-phenylene) bis (4 lb. 1-dodecylpyridi-dimethylbromide), 4,4,-(p-phthalamide) bis (1-octylpyridyl-dimethylbromide), 3,3,1- (mphthalamide) bis (1 year old Pyridi-dimethylbromide), 4,4,1 (1,8 otatamethylenedioxy) bis (1-dodecylpyridi-dimethylbromide), 3,3, — (1,6-hexamethylenedioxy) bis (1 1-hexadodecylpyridi-dimethylbromide), 4,4,1- (1,6-hexamethylenedioxydicarbol) bis (1 year old octylpyridyl-dimethylbromide), 3,3,1- (1,6 —Tetramethylenedioxydicarbol) bis (1-dodecylpyridi-dimethyl bromide), 4,4 '-(1,4-tetramethylenedicarbol-ldioxy) bis (1 year old octyl pyridine-dimethyl bromide), 3,3,1- (p-phthaloyldioxy) bis (1 decylpyridi-dimethoxylate), 4,4'1- (1,8-otatamethylenedicarboxy-ldithioxy) bis (1-octadecylpyridi-di-bromobromide), 3, 3, one (m phthaloyldithio Xy) bis (1-decylpyridi-dimethiodide) and the like. Among these compounds, dimer 38, dimer 38A, dimer 136, dimer 136A and the like are preferably used. For details of the compound of the formula (I), reference can be made to JP-A-2003-252708.

[0053] These compounds having antimicrobial activity can be used alone or in combination of two or more. Among these compounds having an antimicrobial activity, compounds of the formula (I) are preferred. Particularly, when the compound of the formula (I) is combined with other compounds, excellent antimicrobial activity (antibacterial, antiseptic, or antibacterial) is obtained. (Mold effect).

[0054] The content of the 7,8-dihydro wine can be appropriately selected according to the dosage form and application method of the antimicrobial agent, and is not particularly limited. For example, the concentration of 7,8-dihydro-powered wine may be 0.01 to 80% by weight, preferably 0.05 to 50% by weight, more preferably 0.1 to 30% by weight in the antimicrobial agent. %. In the case of aerosols, 7 of the packing in which is filled in a container, 8-dihydro-force wine concentration, for example 0.5 01- 50 wt%, rather preferably is 0. 05 20 wt _^0/0, more preferably about 0.1 1 10 weight ^_0/0.

 [0055] The antimicrobial agent of the present invention can effectively control or prevent specific power plants other than bacteria and yeasts. Examples of the bacteria include bacteria belonging to the genus Bacillus such as Bacillus subtilis (Bacillus subtilis), bacteria belonging to the genus Escherichia such as Escherichia coli (Escherichia coli), and the like. Bacteria belonging to the genus Pseudomonas, such as Pseudomonas aeruginosa; green fe J, can be exemplified.

 [0056] As yeasts, for example, yeasts belonging to the genus Saccharomyces such as Saccharomyces cerevisiae (pan yeast) and Rhodotorula belonging to the genus Rhodotorula rubra such as Rhodotorula rubra. Examples include yeasts.

 The molds include, for example, molds belonging to the genus Alternaria (Alternaria sp.), Such as Alternaria sp., And Cladosporium “Cladosporioides”

(Cladosporium cladosporioides) and other molds belonging to the genus Cladosporium, molds belonging to the genus Fusarium such as Fusarium sp., And Eurotium such as Eurotium tonophilum. ) The genus belonging to the genus can be exemplified. [0058] These microorganisms may adversely affect the human body, etc., as microbes containing spores and the like that not only aesthetically contaminate the inside of a house, but as pathogenic bacteria or as a causative agent of allergic bronchitis or asthma. is there.

 [0059] Further, these microorganisms can grow or reproduce on various substances that can be replaced only by biological substances (eg, plant-derived substances such as cotton and hemp, and animal-derived substances such as wool and leather). Examples of such a substance include resins and the like such as paints, adhesives, and plastic members; rubbers such as natural rubber and synthetic rubber; synthetic fibers and their cloths (such as woven and nonwoven fabrics); Metals such as aluminums and stainless steels; ceramics such as concretes, pottery, and glass; Microorganisms use nutrients that adhere to these substances (e.g., foods, excretions of humans and animals, etc.), which can be grown using these substances as nutrient sources. Can grow.

 For example, specifically, bacteria such as Pseudomonas and fungi such as Cladosporium and Fusarium are easily propagated on cotton and hemp. Bacteria such as the genus Bacillus and molds such as the genus Alternaria and Fusarium tend to breed on wool. Basilas on leather

 Bacteria such as (Bacillus) and molds such as Eurotium easily proliferate! /,

[0061] In addition, resins such as paints, adhesives, and plastic members include Clados polymer.

 Molds such as the genus (Cladosporium), the genus Anorenaria (Alternaria) and the genus Eurotium are easy to breed. Molds such as Alternaria spp. Synthetic fibers include the genus Cladosporium, Alternaria

 Molds such as the genus (Alternaria) and the genus Eurotium tend to breed. Aluminum includes bacteria such as Pseudomonas and Cladosporium.

 Molds such as (Cladosporium) are easy to breed. Yeasts such as Rhodotorula and molds such as Cladosporium and Alternaria spawn easily on concrete. Molds such as the genus Eurotium are easy to breed in glasses!

[0062] Furthermore, nutrients that adhere to these materials include Bacillus spp. Bacteria such as the genus (Escherichia) and the genus Pseudomonas; Saccharomyces

 Yeasts such as Saccharomyces and Rhodotorula; molds such as Alternaria, Cladosporium, Fusarium, and Eurotium are easily propagated. ! /.

 [0063] In the present invention, microorganisms that grow or propagate on the above-described various substances can be appropriately controlled or prevented, so that the microorganisms originate from the growth or propagation of microorganisms that can effectively prevent contamination by microorganisms in a house. Various diseases can be effectively prevented. Furthermore, it is possible to effectively prevent deterioration and embrittlement of the above-mentioned resin and the like, and deterioration of various products (for example, electric products and the like) using such a substance as a component (or member).

 [Method for controlling or preventing microorganisms using antimicrobial agent]

 In the method for controlling or preventing microorganisms of the present invention, the antimicrobial agent can be effectively controlled or prevented by applying the antimicrobial agent to an object to be treated (or a treated part) in which the microorganism can grow or proliferate. . Further, the antimicrobial agent of the present invention can be usefully applied to both home use and industrial use.

 [0065] The substance to be treated (or the part to be treated) is not particularly limited as long as it is a place where a microorganism can grow or proliferate (or a place where a microorganism can proliferate). Or breeding section). Further, the antimicrobial agent may be applied to skin (for example, skin of limbs).

 [0066] For example, the portion to be processed may be in a dry state or a wet state depending on the type of microorganism. For example, the part to be treated may be (i) an article, part or member existing in a non-humid environment (or a dry environment), an article, part or member exposed to a GO wet environment, or (m) water content. An article, a part, or a member that can be brought into contact with the object is exemplified.

[0067] The humid environment refers to, for example, a high humidity of 70 to 100% RH, preferably 80 to 100% RH, more preferably 90 to 100% RH, and particularly preferably about 95 to 100% RH. Environment is acceptable. Also, the frequency (or degree) of exposure of the treated part to a humid environment or the frequency (or degree) of contact with moisture may be intermittent or irregular, which need not be constant or regular. . In addition, contact with moisture includes dew condensation or contact with water droplets rather than just contact with the use of water. [0068] Specifically, (i) articles, parts or members existing in a non-wet environment (or a dry environment) include foods, papers (books and the like), cloths [curtains, covers ( Sofa cover, table cloth, etc.), width or towels, etc.), rugs (carpets, mats, etc.), clothing, shoes, bedding, interior materials [wallpaper (including fat products), flooring , Panels, tatami mats, knockers, filters, etc.), exterior materials [earth and timber, building materials (wall materials, floor materials, ceiling materials, joints, tiles, windows, sashes, ventilation fans, exteriors, etc.), piping, etc.], Furniture (closets, shelves, tapes, chairs, waste bins, etc.), various types of equipment [electronics, electric appliances, precision equipment (cameras, telescopes, binoculars, etc.), etc.], various types of vehicles (vehicles) Aircraft, ships, rockets, etc.) or their components, crafts, soil, plants, etc. That.

 [0069] As the articles, parts or members exposed to the GO wet environment, among the articles, parts or members of the above (i), in addition to those exposed to the wet environment, water surrounding members (for example, faucets, sinks) (Or sink), bath tub, toilet bowl, wash basin, drain hole, etc.), various water supplies [eg, bathroom supplies (eg, basin, bath lid, shower curtain, bath rack, soap dish, soap bottle) , Shampoo or conditioner dispenser, scrubber, bath toy, drain hole packing, trash filter, etc .; kitchenware (triangular corner, sponge, drain bat, cutting board, chopsticks, towels, wash tub, drain hole packing, trash Tableware (ceramics, glass, etc.); Toiletries (toothbrush, cup, cup stand, soap dish, soap bottle, etc.); Supplies (paper holders, toiletries (mats, slippers, toilet seat covers, etc.), auxiliary toilet seats, potties, step tables, toilet brushes, brush cases, satellite cases, soap dishes, soap bottles, etc.) it can.

 [0070] (m) The site or member that can come into contact with moisture is not particularly limited as long as it can come into contact with moisture, and includes, for example, various household or industrial equipment. For example, an air conditioner or an air conditioning system ( Filter, etc.), electric toothbrush (brush section, brush replacement section, etc.), refrigerator (refrigerator room, vegetable room, freezer room, etc.); inner lid of washing machine (especially fully automatic washing machine) or around it , A dehydration tub or the inside of a washing tub or the back side thereof), a humidifier (a tank portion or the like) and the like.

[0071] The method of applying the antimicrobial agent is not particularly limited as long as it can be applied to the object to be treated (or the part to be treated), and various embodiments can be mentioned. For example, the antimicrobial agent is It may be applied to the treatment section) by a method such as dipping, coating, spraying, spraying, pouring, or mixing. Further, the antimicrobial agent is prepared by holding a sheet-like base material such as a synthetic resin sheet, a water-soluble film, paper, and cloth by application, impregnation, kneading, or the like to prepare a sheet material, and the sheet material is treated with the object to be treated. (Or a part to be processed) or the like may be applied or attached. Among these aspects, in order to efficiently apply the composition to an object to be treated (or an object to be treated), it is preferable that the antimicrobial agent is dipped, coated, sprayed, or the like. For example, the antimicrobial agent may be applied by directly or appropriately diluting and immersing the liquid agent, or by applying a liquid agent or a semi-solid agent to be applied. Furthermore, you may apply by spraying a liquid formulation in the form of a mist or a foam.

[0072] Amount object to be processed (or to be processed portion) of the antimicrobial agent with respect to the surface area lm ² of the object (or the processing unit), for example 1 one 500 g, preferably 2-250 g, More preferably, it may be about 3-200 g. In addition, the application amount of 7,8-dihydro power wine to the processed material (or processed portion) is, for example, 30 to 30000 μg / m, preferably 30 to 30000 μg / m, as the concentration in the processed material (or processed portion). It may be 50-15000 g / ml, more preferably about 80-10000 g Zml.

 Industrial applicability

[0073] The antimicrobial agent of the present invention is highly safe for humans and animals and has no detrimental effect on the environment, but has high controllability. It can be used as an antimicrobial agent for natural products, chemical products, ceramic products, metal products, foods, cosmetics, bioactive products, and the components and components of these products. Also, in various highly airtight buildings (for example, houses such as apartment houses, stores, factories, warehouses, hospitals, etc.) and various transportation bodies (for example, vehicles, ships, aircraft, etc.), disinfectants and disinfectants are used. It is suitable as such.

 Example

 Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

Example 11

The test bacteria used in the examples are shown below. [0076] Ba: Bacillus subtilis

 Es: Escherichia coli

 Ps: Nyuetomonas no 'Elkinosa (Pseudomonas aeruginosa)

 Rh: Rhodotorula rubra

 Sa: Saccharomyces cerevisiae

 A1: Alternaria sp.

 CI: Cladosporium cladosporioides

 Fu: Fusarium sp.

 Eu: Eurotium tonophilum

 A glucose agar medium supplemented with a predetermined amount of 7,8-dihydro wine is inoculated with the above test bacteria other than Eurotium tonophilum, and bacteria are incubated at 33 ° C for 18 hours. , Molds and yeasts were cultured at 28 ° C. for 3 days. In addition, instead of the glucose agar medium, Eurotium tonophilum is an agar medium prepared by dissolving potato dextrose (3.9 g), NaCl (5 g), and gnorecose (10 g) in 100 ml of water. The cells were cultured at 28 ° C. for 3 hours. The minimum inhibitory concentration [MIC (μg / ml)] was determined by a multiple dilution method of a predetermined amount. The results are shown in Table 1.

[0077] [Table 1] Table 1

表 1から明らかなように、実施例では、顕著に微生物の生育が阻害された。

As is clear from Table 1, in Examples, the growth of microorganisms was remarkably inhibited.

Example 10 18

100 g of stalks were extracted with 800 ml of acetone at 60 ° C. under reflux. The extract is removed under reduced pressure The extract was concentrated to dryness to obtain an extract. As a result of HPLC measurement, the concentration of 7,8-dihydroca wine in this extract was 19.2% by weight / ⁰ . Met. The above test bacteria are inoculated on a glucose agar medium supplemented with a prescribed amount of this extract and cultured for 18 hours at 33 ° C for bacteria and 3 days at 28 ° C for vitreous and yeast. did. The minimum growth inhibition concentration [MIC (μg / ml)] was determined by the multiple dilution method. Table 2 shows the results.

[0079] [Table 2] Table 2

表 2から明らかなように、実施例では、顕著に微生物の生育が阻害された。

As is clear from Table 2, in Examples, the growth of microorganisms was remarkably inhibited.

Formulation Example 1

 A solution was prepared by dissolving 3 parts by weight of 7,8-dihydro power wine in 97 parts by weight of ethanol.

[0081] Formulation Example 2

 7,8-dihydro power wine 2 parts by weight, Vaseline 5 parts by weight, NAROACTY N100 (manufactured by Sanyo Chemical Industries, Ltd.) 5 parts by weight, propylene glycol 10 parts by weight, ethanol 11 parts by weight An emulsion was prepared by mixing 20 parts by weight of a viscosity agent (1% aqueous solution of carboxyvinyl polymer) and 37 parts by weight of water.

[0082] Formulation Example 3

 Osmolin DA-50 (cationic surfactant type antibacterial agent, manufactured by Sanyo Chemical Industries, Ltd.) 15 parts by weight, 7,8-dihydro wine 1 part by weight, propylene glycol 10 parts by weight, ethanol 50 parts by weight , Water and 24 parts by weight of water to prepare a sprayable solution.

[0083] Formulation Example 4

96.0 parts by weight of ethanol, 3.0 parts by weight of 7,8-dihydro power wine, and hinokitiol 0. 5 parts by weight and 0.5 parts by weight of benzene were mixed to prepare a sprayable solution.

[0084] Formulation Example 5

 98 parts by weight of fatty acid stone (powder) and 2 parts by weight of 7,8-dihydro power wine were mixed and compressed and solidified to prepare a solid preparation (solid stone).

Example 19

 Three plastic chopping boards used at home were collected, and the chopping boards were washed with water and then fractionated into three pieces. In the wet state, the first specimen was sprayed with Formulation Example 1, the second specimen was sprayed with ethanol, and the third specimen was treated without any treatment. All specimens were left for 3 days in an atmosphere of room temperature and high humidity (relative humidity 90%). Bacteria were collected with a food stamp and stamped onto a PDA medium that had previously been solidified in a petri dish. As a result, three days later, the bacteria proliferated violently without treatment, slightly proliferated in the ethanol-disinfected area, and the treated area according to Formulation Example 1 showed almost no growth of the bacteria, confirming a sustained antibacterial effect.

[0086] Example 20

 Four tiles (approximately 10 cm square) were placed on a cruciform plate with a 5 mm gap (joint) and solidified with a caulking agent to prepare test specimens. Similarly, a total of three specimens were prepared. Under high humidity (relative humidity of 95% or more), these specimens were subjected to Alternaria sp. (Alternaria sp.), Kufudoshoriumu (Claaosporium cladosponoides) and Fusarium (Fusarium sp.). The first test specimen, on which the mold had propagated, was washed with a brush and then coated with Formulation Example 1. As a control, the second specimen was used as a control. The same treatment was carried out as for the above test specimen 1 except that ethanol was used in place of the liquid preparation of Preparation Example 1. The third test specimen was washed only, and each specimen was air-dried to remove ethanol. The mixture of the three bacteria was sprayed and placed under the same conditions as those under which mold had developed, and after 2 weeks, no mold was observed in the first specimen treated in Formulation Example 1. Mold development was observed in the other two specimens.

[0087] In the same manner as described above, test specimens were prepared, fungi were propagated, and the test specimens on which the mold had propagated were washed with water. The same operation as in the first test specimen was performed except that the liquid preparation of Preparation Example 4 was sprayed on the obtained test specimen (the fourth test specimen) instead of the liquid preparation of Preparation Example 1. After a week, the development of mold was unrecognizable.

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Claims

Claims [1] An antimicrobial agent containing 7,8-dihydro power wine as an active ingredient, for controlling or preventing at least one microorganism selected from the group consisting of the following (1) and (3).  (1) bacteria,  (2) yeasts,  (3) Molds belonging to at least one genus selected from the genus Alternaria, the genus Cladosporium, the genus Fusarium, and the genus Eurotium  [2] Bacterial power Bacillus, Escherichia, and Pseudomonas 2. The antimicrobial agent according to claim 1, which is at least one selected from the group consisting of (Pseudomonas).  3. The antimicrobial agent according to claim 1, wherein the yeast is at least one selected from the genus Saccharomyces and the genus Rhodotorula.  [4] Molds are also selected as Cladosporium cladosporioides, u-titanium, Eurotium tonophilum, Anoletenolenaria 'S (Alternaria sp.), And Fusarium' Fusarium sp. ' The antimicrobial agent according to claim 1, which is at least one of the following:  [5] The antimicrobial agent according to claim 1, wherein the antimicrobial agent contains 7,8-dihydropower wine contained in an organic solvent extract of a plant belonging to a species of Piper methysticum or a processed product thereof.  [6] An extract obtained by extracting a defatted plant of a plant belonging to the species of Piper methysticum or a processed product thereof with at least one extraction solvent selected from alcohols, esters, and ketones The antimicrobial agent according to claim 1, which contains 7,8-dihydro power wine contained in [7] A method for controlling or preventing a microorganism by applying the antimicrobial agent according to claim 1 to an object to be treated in which the microorganism can grow or proliferate. [8] The method according to claim 7, wherein the antimicrobial agent is applied to a growth or propagation area of the microorganism.