JP2001240507A - Antiseptic, anti-fungal and anti-algal agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an antiseptic, anti-fungal and anti-algal agent. SOLUTION: The antiseptic, anti-fungal and anti-algal agent is characterized by containing two kinds of components as effective components, those are a compound represented by general formula (1) (n denotes 5-77 and the average molecular weight of the compound is 250-2,000), being poly[oxyethylene(dimethyliminio)ethylene(dimethylimino)ethylene dichloride] and a compound represented by general formula (2) (m denotes 3-15 and the average molecular weight of the compound is 700-3,300), being polyhexamethylene biguanide hydrochloride.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an antiseptic and antifungal agent for water treatment of pools, fire protection equipment, fountains, leisure lands, etc., and an antiseptic and antifungal agent for water treatment used in the production process of industrial products. The present invention relates to an antiseptic / fungicidal agent for use on floors, walls, ceilings, etc. of storage locations of industrial raw materials and products, floors for manufacturing products, and an antiseptic and antifungal agent for industrial raw materials and industrial products.

[0002]

2. Description of the Related Art Preservatives and fungicides and antialgal agents are used to prevent various adverse effects (environmental pollution and deterioration by microorganisms) due to the growth and proliferation of bacteria, yeasts, molds and algae. Poly [oxyethylene (dimethyliminio) ethylene (dimethyliminio) ethylene dichloride] (hereinafter referred to as "compound (1)") and polyhexamethylene biguanide hydrochloride, which are the active ingredients of the antiseptic / fungicidal agent of the present invention. Hereinafter, each of which is referred to as “compound (2)”) is known as a fungicidal / fungicidal agent or an algicide.

[0003]

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[0004]

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[0005]

In order to prevent environmental pollution and deterioration by microorganisms, it is necessary to non-selectively and eradicate the generation of various microorganisms such as bacteria, yeasts, filamentous fungi and algae. . However, conventional antiseptics and fungicides and anti-algae agents are often much less effective or difficult to maintain their effects over a long period of time when their use is reduced in consideration of toxicity to humans and animals. Further, few of the conventional drugs sufficiently exhibit both the antiseptic and antifungal effects and the antialgal effect. Both the compound (1) and the compound (2) used in the present invention have such disadvantages, and use of the compound alone is not always satisfactory. Accordingly, development of a novel antiseptic and antifungal agent that has both antiseptic and antifungal effects and antialgal effects and can prevent the generation of various microorganisms for a long period of time with a small amount of medicine, in place of conventional agents, has been required. Requested.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, by using compound (1) and compound (2) together, bacteria, yeast, filamentous fungi, algae, etc. The present invention was found to be useful as an antiseptic and fungicide for preventing environmental pollution and deterioration by various microorganisms, and completed the present invention. That is, the present invention relates to the general formula (1)

[0007]

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(Wherein n represents a number from 5 to 77, and the average molecular weight of the compound is in the range of 1250 to 20,000.) Poly (oxyethylene (dimethyliminio) ethylene (dimethyliminio) ) Ethylene dichloride] and the general formula (2)

[0009]

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(Wherein, m represents a number from 3 to 15, and the average molecular weight of the compound is in the range of from 700 to 3,300.)
And a polyhexamethylene biguanide hydrochloride represented by the formula:

The antiseptic / fungicidal agent of the present invention has a synergistic effect on the antiseptic / fungicidal effect while maintaining the anti-algal effect as compared with the case where the compound (1) or the compound (2) is used alone. Express.

[0012] As a result, it is useful as a preservative and fungicide since it exhibits a strong clean-keeping effect at low dose in water storage facilities and the like.

An antiseptic / fungicidal agent means an agent capable of suppressing the generation of bacteria, mold and algae in a water storage facility or the like, and consequently keeping water clean for a long period of time.

In this case, the generation of algae cannot be suppressed only by the agent having an antiseptic and fungicidal action, and the occurrence of bacteria and mold cannot be suppressed by the agent having an antialgal action alone. It cannot be a fungicide.

It is considered that the antiseptic / fungicidal agent basically needs to have both the antiseptic / fungicidal action and the anti-algal action. Any chemical can be used as long as it can keep the product clean.

The antiseptic and antifungal agents are not limited to water storage facilities,
It can be used wherever water is present in an industrial facility or product where bacteria, mold and algae can develop.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The antiseptic / fungal / algae preventive of the present invention may contain the compound (1) and the compound (2) as active ingredients.

The antiseptic / fungicidal agent of the present invention can also be used as an antiseptic / antifungal agent or an antialgal agent.

The preparation of the antiseptic / fungicidal agent of the present invention is prepared by adding an appropriate carrier and an auxiliary agent such as a surfactant and a binder to the active ingredient containing the compound (1) and the compound (2) used in the present invention. , Stabilizers and the like are mixed and mixed, and formulated into wettable powders, emulsions, liquids, sols (flowables) and other suitable dosage forms according to conventional methods.

When these preparations are prepared, the compounding amount of the active ingredient containing the compound (1) and the compound (2) is limited as long as a wettable powder, an emulsion, a liquid, a sol and other suitable preparations can be prepared. Although not particularly limited, it is in the range of 1-90% by weight, preferably 10-80% by weight, based on the weight of these preparations.

As the carrier that can be used, any solid or liquid can be used as long as it is commonly used for industrial antibacterial and antifungal agents and algicides, and it is not limited to a specific carrier.

Examples of solid carriers include mineral powders such as kaolin, bentonite, clay, montmorillonite, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phosphorous lime, white carbon, slaked lime, silica sand, ammonium sulfate, urea and the like, or Vegetable powders such as soybean flour, starch, crystalline cellulose, etc., alumina, silicates, sugar polymers, highly dispersible silicic acids, waxes and the like can be mentioned.

Examples of liquid carriers include water, alcohols such as methyl alcohol, ethyl alcohol, n-
Propyl alcohol, isopropyl alcohol, ethylene glycol, propylene glycol, benzyl alcohol and the like, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene and the like, or halogenated hydrocarbons,
For example, chloroform, dichloromethane, ethylene dichloride and the like, ethers such as ethyl ether, dioxane, tetrahydrofuran and the like, ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, ethylene glycol acetate, Amyl acetate and the like, nitriles such as acetonitrile, propionitrile, acrylonitrile and the like, sulfoxides such as dimethylsulfoxide and the like, alcohol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and the like, amines such as triethylamine and the like, and Aliphatic and alicyclic hydrocarbons such as n-hexane and cyclohexane, and industrial gasoline (petroleum ether , Solvent naphtha, etc.), and petroleum fractions (paraffins, kerosene, gas oil, etc.), and the like.

Emulsions, wettable powders, sols (flowables),
For preparations such as liquids, emulsification, dispersion, solubilization, wetting,
A surfactant may be added for the purpose of spreading or the like.

Examples of such a surfactant include the following, but are not limited thereto.

Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester and sorbitan alkyl ester.

Examples of the anionic surfactant include alkyl benzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate and lauryl sulfate.

Examples of the cationic surfactant include alkylamines (laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.).

Examples of the amphoteric surfactant include carboxylic acid (betaine type) sulfate and the like.

In addition to these, polyvinyl alcohol (PVA), carboxymethyl cellulose (CM
C), gum arabic, polyvinyl acetate, gelatin, casein, sodium alginate, tragacanth gum,
Thickeners such as guar gum, xanthan gum and hydroxypropylcellulose and various adjuvants can be blended.

If necessary, an appropriate amount of a stabilizer such as an antioxidant, an ultraviolet absorber or the like can be added.

The antiseptic / fungicidal agent of the present invention can be used by further containing other known antiseptic / fungicidal agents or antialgal agents, if necessary.

The following are typical examples, but the present invention is not limited to these examples.

Quaternary ammonium compounds such as N, N-didecyl-N, N-dimethylammonium chloride and benzalkonium chloride; aldehyde compounds such as glutaraldehyde; 1,2-dibromo-2,4-dicyanobutane;
2,2-dibromo-3-nitrilopropionamide, 2
-Bromo-2-nitropropanediol, 5-bromo-
Halogenated compounds such as 5-nitro-1,3-dioxane; N-halogen compounds such as bromochlorodimethylhydantoin and trichloroisocyanuric acid; guanide compounds such as poly (hexamethylene biguanide) hydrochloride; zinc dimethyldithiocarbamate; Zinc diethyldithiocarbamate, zinc dibutyldithiocarbamate, zinc ethylphenyldithiocarbamate, zinc ethylenebisdithiocarbamate, zinc propylenebisdithiocarbamate, bis (dimethyldithiocarbamoyl)
Dithiocarbamate-based metal compounds such as zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, nickel dimethyldithiocarbamate, nickel dibutyldithiocarbamate, copper dimethyldithiocarbamate, and iron dimethyldithiocarbamate; copper powder;
Copper-based metal powders such as copper-nickel alloy powder; copper such as cuprous oxide, cuprous thiocyanate (copper rhodan), basic copper carbonate, copper pyrophosphate, copper naphthenate, copper abietic acid, copper oxyquinoline Pyridion-based metal compounds such as zinc salt of 2-pyridinethiol-1-oxide and copper salt of 2-pyridinethiol-1-oxide; tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetra-n-propylthiuram disulfide , Tetraisopropylthiuram disulfide, tetra-n-butylthiuram disulfide, tetraisobutylthiuram disulfide, N, N'-ethylenebisthiocarbamoylsulfide, N, N'-propylenebisthiocarbamoylsulfide, N, N'-butylene Conversion of thiurams such as bisthiocarbamoyl sulfide Compound; 2- (4-thiazolyl) benzimidazole, 2- (methoxycarbonylamino) benzimidazole, methyl-1- (ω-cyanopentylcarbamoyl) -2-benzimidazole,
Benzimidazole compounds such as zinc mercaptobenzimidazole and 2-thiocyanomethylthiobenzimidazole; 2-mercaptobenzothiazole,
(Thiocyanomethylthio) benzothiazole, 2- (thiocyanomethylsulfonyl) benzothiazole, 2-thiocyanoethylthio-4-chlorobenzothiazole, 2
-Thiocyanopropylthio-5,7-dichlorobenzothiazole, 2-thiocyanomethylthio-4,5,6,7
Benzothiazole compounds such as tetrachlorobenzothiazole; tetrafluoroisophthalonitrile, tetrachloroisophthalonitrile, 5-chloro-2,4-difluoro-6-methoxyisophthalonitrile, 2,4,4
Nitrile compounds such as 5,6-tetrachloroisophthalonitrile; 5-chloro-2-methyl-3-isothiazolone, 5-chloro-2-n-decyl-3-isothiazolone, 4,5-dichloro-2- ( 4-chlorobenzyl)-
3-isothiazolone, 4,5-dichloro-2- (4-chlorophenyl) -3-isothiazolone, 4,5-dichloro-2-n-hexyl-3-isothiazolone, 4,5-
Trimethylene-2-methyl-3-isothiazolone, 4-
Methyl-5-chloro-2-n-octyl-3-isothiazolone, 2-methyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-4-isothiazoline-3-
Isothiazoline-based compounds such as on, 2-n-octyl-4-isothiazolin-3-one and 1,2-benzoisothiazolin-3-one; 1- [2- (2,4-dichlorophenyl) -4-propyl-1 , 3-Dioxolanyl-
2-methyl] -1H-1,2,4-triazole, 4,
Triazole compounds such as 4-dimethyl-2 (1,2,4-triazol-1-yl) -1- (4-trifluoromethyl-2-chlorophenyl) -1-penten-2-ol; 5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,3,6-trichloro-4
-Propylsulfonylpyridine, 2,6-dichloro-
Pyridine compounds such as 3,5-dicyano-4-phenylpyridine; 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 2-chloro-4-methylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis (ethylamino) -s-triazine,
2-chloro-4,6-bis (isopropylamino) -s
-Triazine, 2-methylthio-4,6-bis (ethylamino) -s-triazine, 2-methylthio-4-ethylamino-6-isopropylamino-s-triazine,
Triazine-based compounds such as 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine; N- (3,4-dichlorophenyl) -N′-methylurea, 3- (3,4-dichlorophenyl) ) -1,1-Dimethylurea, 3- (3,4-dichlorophenyl) -1-
Methoxy-1-methylurea, 1- (α, α′-dimethylbenzyl) -3-methyl-3-phenylurea, 1- (2
-Methylcyclohexyl) -3-phenylurea, 3-
Urea compounds such as (4-isopropylphenyl) -1,1-dimethylurea; 2,3-dichloro-1,4-naphthoquinone, 2-amino-3-chloro-1,4-naphthoquinone, 2,3-dicyano Quinone compounds such as -1,4-dithiaanthraquinone; N-trichloromethylthiotetrahydrophthalimide, N-1,1,2,2-tetrachloroethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide, N-fluorodichloromethylthiophthalimide, N , N-Dimethyl-N'-phenyl-N '-(fluorodichloromethylthio) sulfamide, trichloromethylthiomethanesulfone-p-chloroanilide, N- (1,1,2,2, -tetrachloro-2-fluoroethylthio) ) Methanesulfonanilide,
N-fluorodichloromethylthio-N-3-chlorophenyl-N'-dimethylurea, N-fluorodichloromethylthio-N-3,4-dichlorophenyl-N'-methylurea, N-fluorodichloromethylthio-N-trissulfonyl-N N-haloalkylthio compounds such as -methylamine; N-phenethyldichloromaleimide;
Benzyldichloromaleimide, N- (2-chlorophenyl) maleimide, N- (4-fluorophenyl) maleimide, N- (3,5-dichlorophenyl) maleimide,
N- (2,4,6-trichlorophenyl) maleimide,
N-4-tolylmaleimide, N-2,4-xylylmaleimide, 2,3-dichloro-N- (2 ′, 6′-diethylphenyl) maleimide, 2,3-dichloro-N- (2 ′
-Methyl-6'-diethylphenyl) maleimide, 2,
3-dichloro-N- (2 ', 6'-dimethylphenyl) maleimide, 2,3-dichloro-N- (2', 4 ', 6'-
Maleimide compounds such as trimethylphenyl) maleimide; 3,5-dimethyl-tetrahydro-1,3,5,
2 (H) -thiadiazin-2-one, 3,3′-ethylenebis (tetrahydro-4,6-dimethyl-2H-1,
3,5-thiadiazin-2-one, 3,5-dimethyl-
2-thiotetrahydro-1,3,5-thiadiazine,
Thiadiazine-based compounds such as 3,5-dibenzyltetrahydro-1,3,5-thiadiazine-2-thione; methyl thiocyanate, chloromethyl thiocyanate, ethyl thiocyanate, methylenebisthiocyanate, chloromethylenebisthiocyanate, ethylenebisthiocyanate Chloroethylene bisthiocyanate, isobornyl thiocyanate, methyl isothiocyanate, allyl isothiocyanate, phenyl isothiocyanate,
Thiocyan compounds such as benzyl isothiocyanate;
Alkyl phenol compounds such as capryl phenol and nonyl phenol; tris (octyl phenyl) phosphite, tris (nonyl phenyl) phosphite, tris (dinonyl phenyl) phosphite, tris (mono,
Alkyl phenyl phosphite compounds such as di-mixed nonylphenyl) phosphite; alkyls such as tris (octyl phenyl) phosphate, tris (nonyl phenyl) phosphate, tris (dinonyl phenyl) phosphate and tris (mono, di-mixed nonyl phenyl) phosphate Phenyl phosphate compound; O-3-iodo-2-propynyl-N-butyl carbamate, N-3-
Iodo-2-propynyl-O-butyl carbamate,
Iodine compounds such as 2,3,3-triiodoallyl alcohol and diiodomethylparatolylsulfone; polysulfide compounds such as n-octylchloromethyl disulfide; boron compounds such as pyridinetriphenylborane; phenyl (bispyridyl) bismuth dichloride and the like Bismuth compounds.

Compound (1) and compound (2) of the present invention
The antiseptic / fungus / algae preventive agent containing as an active ingredient can be used for the following applications. 1) Antiseptic, mold and algae for water treatment of pools, fire protection equipment, fountains, leisure lands, etc. 2) Antiseptic and antifungal algae for water treatment used in building air conditioning and manufacturing processes of industrial products, for example, preservation of cutting oil; cooling towers in factory manufacturing equipment and building air conditioning; disinfection and pulp and paper mills; Prevent slime formation; protect slime deposits on sugarcane and sugar beet sugar production equipment; prevent microbial accumulation and deposition in air washers, scrubber systems and industrial freshwater supply systems; oilfield cutting oil, muddy water and secondary oil recovery processes Prevention of microbial contamination and sedimentation in plants; prevention of microbial accumulation in photographic processing. 3) Antiseptic, fungus- and alga-proofing used on floors, walls, ceilings, etc. of storage locations for industrial raw materials and products, product manufacturing locations, etc.
Protection against attack by bacteria, fungi, and algae that occur while the paint film, especially the paint film of the exterior paint, is exposed to the elements; weather; maintenance of sanitary conditions in food factories; washing of manufacturing facilities, sewage treatment plants, and human waste Deodorant sterilization of treatment plants. 4) Preservatives and fungicides of industrial raw materials and products, for example, water-based paints, adhesives, latex, emulsion products such as acrylics, starches, pigments, slurry products such as calcium carbonate, and bacteria in joint cement, Inhibition of fungal and algae growth; preservation of wood of building materials (building materials, civil engineering materials, etc.); fungicide of surfactants; antibacterial and antifungal treatment by spraying or dipping fibers, fabrics and leather; vinyl chloride, polyurethane Interior / exterior materials (for housing and medical facilities), building materials (building materials, civil engineering materials, etc.), home appliances, household goods, made of resins such as polyethylene, polypropylene, silicone, modified silicone, nylon, epoxy, etc.
Antibacterial / antifungal and anti-algae for sporting goods; prevention of growth of bacteria and fungi in paper coating materials and coating processing; prevention of microbial contamination of cosmetics and toiletry products;
Prevent microbial contamination of electrodeposition systems, diagnostic and pharmaceutical products, medical equipment, etc.

Compound (1) is disclosed in US Pat. No. 3,771,9.
No. 89 and U.S. Pat. No. 4,250,269, and a commercially available product can be used as it is.

In the structural formula of the compound (1), the value of n is 5
And the average molecular weight of compound (1) is 12
It is in the range of 50 to 20,000.

Compound (2) is disclosed in British Patent 702,268.
No. 1,152,243 and British Patent 1,1
No. 67,249, and can be synthesized.
Alternatively, a commercially available product can be used as it is.

In the structural formula of the compound (2), the value of m is 3
And the average molecular weight of compound (2) is 70.
It is in the range of 0-3300.

The compounding ratio (weight ratio) of compound (1) to compound (2) is 0.05 to 19 (compound (1) / compound (2)), preferably 0.2 to 10 (compound (1)). / Compound (2)), more preferably 0.2 to 5 (compound (1) / compound (2)), still more preferably 1 to 5 (compound (1) / compound (2)), and still more preferably 2 to 5. A range of 5 (compound (1) / compound (2)) can be used.

Formulation examples when the active ingredients containing the compound (1) and the compound (2) are used as industrial antibacterial and antifungal agents and algicides are shown below. The type and amount of the agent are not limited to these.

[0042]

Table 1 Formulation Example 1 (Liquid) Ingredient% by weight Active ingredient (Compound 1 + Compound 2) 40 Ethylene glycol 10 Distilled water 50 100

By mixing and dissolving the above, a liquid preparation containing 40% of the active ingredient was obtained.

[0044]

Table 2 Formulation Example 2 (Liquid) Ingredient% by weight Active ingredient (Compound 1 + Compound 2) 40 Propylene glycol 10 Distilled water 50 100

By mixing and dissolving the above, a liquid preparation containing 40% of the active ingredient was obtained.

[0046]

Table 3 Formulation Example 3 (Emulsion) Ingredient% by weight Active ingredient (Compound 1 + Compound 2) 30 Distilled water 20 Dimethyl sulfoxide 45 Methyl isobutyl ketone 2.5 Solpol 800A 2.5 (Emulsifier manufactured by Toho Chemical Co., Ltd.) １００ 100

By mixing and dissolving the above, an emulsion containing 30% of the active ingredient was obtained.

[0048]

Table 4 Formulation Example 4 (Wettable powder) Ingredient% by weight Active ingredient (Compound 1 + Compound 2) 20 Distilled water 12 Lauryl sulfate 5 Clay 63 100

The above ingredients are uniformly mixed and pulverized to obtain an active ingredient of 20%
Was obtained.

[0050]

Table 5 Formulation Example 5 (Floable agent) Ingredient% by weight Active ingredient (Compound 1 + Compound 2) 30 Lauryl sulfate 2 Xanthan gum 2 Hydroxypropylcellulose 1 Distilled water 65 100

The above composition was placed in a ball mill and pulverized and mixed for 12 hours to obtain a flowable composition containing 30% of the active ingredient.

The preservative and fungicide compositions of the present invention can be applied to various preparations as they are or after dilution with water or a suitable organic solvent.

When used as an antiseptic and fungicidal agent for industrial raw materials and industrial products, they can be added to or mixed with various industrial raw materials or products, or can be applied to the surfaces of various industrial raw materials or products by coating or Industrial methods that have been commonly used in the past, including a method of spraying or a method of dipping various industrial raw materials and products in a diluent of the industrial antibacterial / antifungal agent and algicide of the present invention, etc. It can be used by various methods according to the method of use of the antibacterial / antifungal agent and the algicide for use, but is not limited to any particular method.

[0054]

EXAMPLES The present invention will be described below in more detail with reference to examples using the compounds of the present invention. However, the present invention is not limited to these examples.

Example 1 (Evaluation of antibacterial and antifungal activities)

Solution 1: Compound 1 solution (60% compound 1, 40% water) Solution 2: Compound 2 solution (20% compound 2, 80% water) Solution 3 Mixed solution of Solution 1 and Solution 2 (Solution 1) : Solution 2 =
2: 1)

Each of the above solutions was diluted with dimethyl sulfoxide to prepare solutions having various concentrations. For this, 0.5 ml of the above solution was added to 9.5 ml of each, and the mixture was added to a petri dish using a susceptibility medium-N (Nissui Pharmaceutical) for bacteria and a potato dextrose agar medium (Nissui Pharmaceutical) for fungi. The solidified plate was poured. The inoculated bacteria were cultured for 20 hours at 37 ° C. in a bouillon for sensitivity measurement (Nissui Pharmaceutical), and the fungi were cultured for 10 days on a potato dextrose agar medium (Nissui Pharmaceutical), each having 10 ⁶ CFU / ml.
Was prepared. The suspension of the test bacteria was streaked on a drug-mixed agar plate using a platinum loop, and 37 ± 1 for bacteria.
C. for 18 to 20 hours and for fungi at 27.degree. C. for 7 days, and the concentration at which no growth was observed was defined as the minimum inhibitory concentration (MIC). However, the density (pp
m) represents the concentration of the solution itself (including water), not the concentration of the compound. The results are shown in Table 1. However, the symbols in the table mean the following.

A: Bacillus subtilis B: Escherichia coli C: Rhodotorula muciginosa
laginosa) D: Trichophyton mentagrophytes
yton mentagrophytes)

[0059]

TABLE 1 Activity against bacteria and fungi 溶液 Solution MIC (ppm) ABCD ───────────────────────── 1 200 780 780 780 2 3.9 200 200 1560 3 7.8 62.5 100 780 ────── ───────────────────

Solution 1 showed almost no antibacterial / antifungal activity. Solution 2 is Bacillus subtilis (Bacillus
subtilis), but showed little activity against other bacteria. Since the solution 3 is a mixed solution of the solution 1 and the solution 2, it is expected that the solution 3 has an intermediate activity between the solution 1 and the solution 2. However, the actual activity showed antibacterial and antifungal activity equivalent to or higher than that of Solution 1 and Solution 2. Therefore, it became clear that the antibacterial and antifungal activities were enhanced (synergistic action) by mixing Compound 1 and Compound 2.

Example 2 (Evaluation of growth inhibitory activity against freshwater green algae) In addition to the solutions 1 to 3 prepared in Example 1, the following solutions were prepared.

Solution 4 A mixed solution of Solution 1 and Solution 2 (Solution 1: Solution 2 =
3: 1) Solution 5 A mixed solution of Solution 1 and Solution 2 (Solution 1: Solution 2 =
4: 1) Solution 6 A mixed solution of Solution 1 and Solution 2 (Solution 1: Solution 2 =
5: 1)

Solutions 1 to 6 were each diluted with dimethyl sulfoxide to prepare solutions having various concentrations. Freshwater green algae in the logarithmic growth phase (Selenastrum capricornutum,
(Selenastrum capricornutum) Each of the above solutions was added to a medium containing 10 ⁴ / ml to prepare samples of various concentrations.
The culture was allowed to stand still at 3 ± 1 ° C. for 24 hours under continuous lighting conditions. 72
After a period of time, the number of cells was measured using a hemocytometer to show the growth inhibitory activity as EC ₅₀ (concentration that inhibits proliferation by 50%) and EC ₉₀ (concentration that inhibits proliferation by 90%).
However, the concentration (ppb) shown is not the concentration of the compound but the concentration of the solution itself (including water). The results are shown in Table 2.

[0064]

[Table 7]

Both Solution 1 and Solution 2 showed high growth inhibitory activity. Since the solution 3 is a mixed solution of the solution 1 and the solution 2, it is expected that the solution 3 has an intermediate activity between the solution 1 and the solution 2. However, the actual activity is between solution 1 and solution 2
The above growth inhibitory activity was demonstrated. Therefore, it was clarified that by mixing Compound 1 and Compound 2, the growth inhibitory activity was enhanced (synergistic action).

Example 3 (Evaluation of growth inhibitory activity against green algae isolated and cultured from pool water) Solutions 1 to 3 prepared in Example 1 were diluted with dimethyl sulfoxide to prepare solutions having various concentrations. Green algae in logarithmic growth phase (A: genus Chlorococcum, B: Choric
ystis genus, C: Chlorella genus) The above solutions were added to a medium containing 10 ⁴ / ml to prepare samples of various concentrations.
The culture was allowed to stand still at 3 ± 1 ° C. for 24 hours under continuous lighting conditions. 16
Eight hours later, the number of cells was measured using a hemocytometer to show the growth inhibitory activity as EC ₉₀ (concentration that inhibits proliferation by 90%). However, the concentration (ppm) shown is not the concentration of the compound but the concentration of the solution itself (including water). The results are shown in Table 3.

[0067]

[Table 8] Activity against green algae isolated and cultured from pool water ─────────────── ―――――― Solution Growth inhibitory concentration: EC ₉₀ (ppm) No . Green algae A Green algae B Green algae C ──────────────── ―――――― 1 12.0 2.7 10 2 2.3 0.6 2.3 3 1.9 0.6 6.8 ――――――――――― ――――――――――

Solution 1 showed low growth inhibitory activity against green algae A (genus Chlorococcum), while solution 2 showed high growth inhibitory activity. Since the solution 3 is a mixed solution of the solution 1 and the solution 2, it is expected that the solution 3 has an intermediate activity between the solution 1 and the solution 2. However, the actual activity showed a growth inhibitory activity (synergistic action) of the solution 2 or more. Solution 1 and solution 2 both showed high growth inhibitory activity against green algae B (genus Choricystis). Solution 3 showed almost the same activity (additive action) as Solution 1 and Solution 2. Solution 1 showed low growth inhibitory activity against green algae C (genus Chlorella), while solution 2 showed high growth inhibitory activity. Since the solution 3 is a mixed solution of the solution 1 and the solution 2, it is expected that the solution 3 has an intermediate activity between the solution 1 and the solution 2. The actual activity showed, as expected, an intermediate growth inhibitory activity (additive effect) between solution 1 and solution 2. As described above, the solution 3 exhibited the same or higher growth inhibitory activity as the solutions 1 and 2 in all the species of the green algae isolated and cultured from the pool water. Therefore, compound 1 and compound 2
Is expected to enhance (synergistic effect) the growth-inhibiting activity of green algae in the pool water.

Example 4 (Practical tests in three pools where the occurrence of algae has already been confirmed) The solution 3 prepared in Example 1 was added to each of the three pools at a concentration of 20 ppm (not the concentration of the compound but the solution). The concentration of the algae itself) and the change in the number of algae over time were measured. The results are shown in Table 4.

[0070]

[Table 9] Table 4 Field tests in pools where the occurrence of algae has already been confirmed ─────────────── ―――――― ───────── ──── Pool Alga species Algae count result (cells / ml) No. No. Before treatment 1 week after 2 weeks 3 weeks after 4 weeks ──────────────── ―――――― ───────────── 1 16,800 167 0 0 0 625 220 0 0 0 2 12,000 0 0 0 0 469 0 0 0 0 3 1,690 0 0 0 0 ――――――――――――――――――――― ─── ──────────

Algae species No. : Green algae, oval single cell (Tetrastrum s
p.) Algae species No. : Green algae, Tsuzumimo (Cosmarium sp.)

The solution 3 was applied at a dosage of 20 ppm (the concentration of the solution itself, not the concentration of the compound), and was effective for all algae present in the pools 1 to 3 within 2 weeks after the introduction. It was clarified that the algae-preventing effect was maintained even at the time of.

[0073]

The composition containing compound 1 and compound 2 has high safety, exhibits a wide spectrum at a low dose, and is useful as a preservative and fungicide.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C08L 79/02 C08L 79/02 F-term (Reference) 4H011 AA02 AA03 AD01 BA01 BA06 BB04 BB11 BC03 BC05 BC07 BC18 BC19 BC20 DA13 DA15 DC04 DD01 DH02 DH03 DH10 DH14 4J002 CH01W CH05W CM00X CM01W CM01X ER026 FD186 GT00

Claims (3)

[Claims] 1. An active ingredient represented by the following general formula (1): (Wherein, n represents a number from 5 to 77, and the average molecular weight of the compound is in the range of 1250 to 20,000.) Poly [oxyethylene (dimethyliminio) ethylene (dimethyliminio) ethylene dichloride And the general formula (2) (Wherein m represents a number from 3 to 15 and the average molecular weight of the compound is in the range of from 700 to 3300). It is characterized by containing two kinds of components, namely polyhexamethylene biguanide hydrochloride represented by the following formula: Antiseptic and antifungal agents. 2. The weight ratio of the compound represented by the general formula (1) to the compound represented by the general formula (2) (general formula (1) / general formula (2)) is 0.05 to 19. The antiseptic / antifungal agent according to claim 1, which is in a range. 3. The weight ratio of the compound represented by the general formula (1) to the compound represented by the general formula (2) (general formula (1) / general formula (2)) is in the range of 1 to 5. 3. The antiseptic / fungus / algae inhibitor according to claim 2.