Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F1/00—Treatment of water, waste water, or sewage
  • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F1/00—Treatment of water, waste water, or sewage
  • C02F1/72—Treatment of water, waste water, or sewage by oxidation
  • C02F1/76—Treatment of water, waste water, or sewage by oxidation with halogens or compounds of halogens
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
  • Y02W10/00—Technologies for wastewater treatment
  • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
  • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

Definitions

• the present invention relates to an algicide / bactericidal agent.
• the algicidal / bactericidal agent of the present invention is used to suppress the growth and proliferation of algae and general bacteria generated in aqueous systems.
• the water system is not limited to this, but circulating cooling water such as cooling towers, various industrial water, waste water, ponds, lakes, reservoir spillways, fountains, and sunlight (in environments such as building exteriors) It also refers to water systems that come into contact with the atmosphere.
• triazine-based algicides such as amethrin, simethrin, promethrin and the like are used because of their high efficacy as algicides. Handbook "(1998 edition Japan Plant Protection Association edition) ⁇ .
• these triazine-based algicides have low solubility in water, and it is necessary to add a large amount of an organic solvent for formulation. When added to an aqueous system, the organic solvent in the formulation is a nutrient for general bacteria. There were problems such as becoming a source. In addition, these triazine-based algicides have problems in terms of safety such as toxicity and carcinogenicity.
• bactericides for suppressing the growth and proliferation of general bacteria include isothiazolone compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2-bromo-2-nitropropane-1, An organic bromine-based compound represented by 3-diol is used (Patent Document 1 and Patent Document 2).
• isothiazolone compounds have strong toxicity, skin irritation and mucous membrane irritation and are inconvenient to handle, and organic bromine compounds have the disadvantage that they have a relatively strong effect on general bacteria but a weak algaecidal effect. .
• N-chlorosulfamic acid or N, N-dichlorosulfamic acid or a salt thereof formed by adding sulfamic acid or a salt thereof to this hypochlorite is bound chlorine, and hypochlorous acid It is known that its bactericidal effect is inferior to free chlorine such as. Bonded chlorine is less likely to cause problems such as corrosion of piping and equipment in the system at high concentrations, although its oxidizing power is reduced compared to free chlorine.
• the algicidal effect of halogen-based oxidizing agents such as hypochlorous acid is lower than that of triazine-based algicidal agents such as amethrin described above, and bound N-chlorosulfamic acid is the same.
• halogen-based oxidizing agents such as hypochlorous acid
• triazine-based algicidal agents such as amethrin described above
• bound N-chlorosulfamic acid is the same.
• a high concentration is required, and as a result, there is a problem that the risk of causing corrosion of piping and equipment in the system is increased.
• currently used drugs have various drawbacks in terms of solubility in water, cost, handleability, safety and the like, and are not always satisfactory.
• N-chloro-2-pyrrolidinone which is one of the algicidal / bactericidal components of the present invention, is used as a disinfectant / bleaching agent in combination with N-chloro-5-methyl-2-oxazolidinone in Patent Document 4.
• Patent Document 4 There is a report, but there is no description about the algicidal effect.
• methods for blending 2-pyrrolidinone with sulfamic acid or hydantoin as N-hydrogen compounds for the purpose of stabilizing hypochlorous acid have been reported in Patent Document 5 and Patent Document 6, but 2-pyrrolidinone is only used.
• N-hydrogen compounds such as these are formulated for the purpose of stabilizing hypochlorous acid, and have not been evaluated as bonded N-chloro compounds or N, N′-dichloro compounds shown in the present invention. There is no mention of the algaecidal effect.
• Patent Document 7 reports a microorganism control method using dimethylhydantoin in combination with free halogen and N-hydrogen compounds, and there is a description of 2-pyrrolidinone as one of N-hydrogen compounds. Has not been evaluated, and there is no mention of the algicidal effect.
• An object of the present invention is to provide an algicidal agent and an algicidal / bactericidal agent that are excellent in solubility in water, low in cost, and excellent in handleability.
• the subject of the present invention also provides a method for controlling algae and / or bacteria in an aqueous system in contact with a metal member where corrosion is not desired.
• the present invention provides: (1) an algicidal agent containing N-chloro-2-pyrrolidinone, (2) The algicidal agent according to (1), which is a water-soluble liquid preparation further comprising water or a mixed solution of water and a water-soluble organic solvent, (3) Formula (I):
• X represents a methylene group, a secondary amino group or an N-chloro group
• R represents an alkylene group having 2 to 5 carbon atoms, provided that when X is an N-chloro group, R represents a carbon atom.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam, N-chloro- ⁇ -hepta.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is N-chloro-2-pyrrolidinone, N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam N-chloro- ⁇ -heptalactam, N-chloro-2-imidazolidinone, N, N′-dichloro-2-imidazolidinone, N-chloro-tetrahydro-2-pyrimidinone, and N, N′-dichloro -Algae / sterilization method according to (6), characterized in that it is at least one selected from tetrahydro-2-pyrimidinone, (8) Use of N-chloro-2-pyrrolidinone to kill algae, (9) Algae killing method using N-chloro-2-pyrrol
• Algae method (where "algae control is desired” refers to, for example, an aqueous system), (10) Use of N-chloro-2-pyrrolidinone for the production of an algicide (11) Method for producing an algicide using N-chloro-2-pyrrolidinone; specifically, N-chloro-2 -A method for producing an algicide, comprising a step of blending pyrrolidinone (the method may further comprise a step of blending other components as appropriate), (12) One kind selected from cyclic N-chloro compounds represented by formula (I) (excluding N-chloro-2-pyrrolidinone) or N, N′-dichloro compounds for algaecidal / sterilizing Use of the above compounds, (13) The cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam, N-chloro- ⁇ -hepta
• a target for which control of algae and / or bacteria is desired refers to, for example, an aqueous system
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam, N-chloro- ⁇ -hepta.
• Method for producing algicide / bactericidal agent specifically, a method for producing algicide / bactericidal agent, comprising the step of blending the compound (this method may further comprise a step of blending other components as appropriate) it can),
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam, N-chloro- ⁇ -hepta.
• algicidal / bactericidal agent refers to “algicidal and / or bactericidal agent”.
• the “algaecidal / sterilizing method” refers to “a method of controlling algae and / or bacteria”.
• Algae-killing refers to “controlling algae and / or bacteria”.
• algae control refers to, for example, suppression or prevention of algae growth or proliferation.
• control of algae and / or bacteria refers to suppression or inhibition of growth or proliferation of algae and / or bacteria, for example.
• an algicide / disinfectant composition that has excellent solubility in water, exhibits excellent algicidal and bactericidal effects, and is low in cost and easy to handle, It can be handled as a liquid formulation, has excellent solubility in water, is stable in aqueous solution, and exhibits excellent algicidal and bactericidal effects, even though effective chlorine is a combined N-chloro or N, N'-dichloro compound. Furthermore, the present inventors have found an algicidal / bactericidal composition having low corrosive properties and excellent handleability, and has reached the present invention.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) can be handled as an aqueous solution because it dissolves in water at an arbitrary ratio. It has also been found that the aqueous solution is stable and maintains an effective chlorine concentration.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) of the present invention is a hypothetical compound in water such as the corresponding N-hydrogen cyclic amide compound and sodium hypochlorite. Another advantage is that it can be prepared as a stable aqueous solution at a low cost by mixing with a compound that generates chloric acid.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) of the present invention is extremely low in corrosiveness and corrodes equipment and piping even when used at a high concentration. It is also an advantage that the risk of falling is low.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) is preferably N-chloro-2-pyrrolidinone, N-chloro-2-piperidone, N-chloro- ⁇ -caprolactam, N-chloro- ⁇ -heptalactam, N-chloro-2-imidazolidinone, N, N′-dichloro-2-imidazolidinone, N-chloro-tetrahydro-2-pyrimidinone, and N, N One or more selected from '-dichloro-tetrahydro-2-pyrimidinone.
• algicidal agent and “algicidal / bactericidal agent” each contain at least a predetermined active ingredient and may contain other ingredients, or an algaecidal compound or composition, In addition, it refers to a compound or composition for algicidal and / or sterilizing.
• Examples of the above-mentioned other components include media such as diluents and excipients for formulation, and other active ingredients.
• Other components can be selected from known components as long as the stability is not impaired.
• the algicidal agent and algicidal / bactericidal agent of the present invention may be formulated into an arbitrary form.
• the cyclic N-chloro compound or N, N′-dichloro compound represented by the formula (I) of the present invention is dissolved in water or a mixed solution of water and a water-soluble organic solvent. And water-soluble liquid preparations.
• water-soluble organic solvents include organic acids such as lactic acid, formic acid, acetic acid and citric acid, ketones such as acetone, alcohols such as ethanol, glycols such as ethylene glycol, glycol ethers such as diethylene glycol monomethyl ether, diethyl carbonate And esters such as tetrahydrofuran, ethers such as tetrahydrofuran, cyclic amides, and chain amides such as dimethylformamide.
• organic acids such as lactic acid, formic acid, acetic acid and citric acid
• ketones such as acetone
• alcohols such as ethanol
• glycols such as ethylene glycol
• glycol ethers such as diethylene glycol monomethyl ether
• diethyl carbonate And esters such as tetrahydrofuran, ethers such as tetrahydrofuran, cyclic amides, and chain amides such as dimethylformamide.
• bactericidal active ingredient can be added to the algicidal / bactericidal agent of the present invention within a range not impairing the stability.
• organic bromonitro compounds such as 2,2-dibromo-2-nitroethanol and 2-bromo-2-nitropropane-1,3-diol, and 5-chloro-2-methyl-4-isothiazoline.
• Isothiazolone compounds such as -3-one and 2-methyl-4-isothiazolin-3-one
• dithiocarbamate compounds such as dimethyldithiocarbamate
• thiazole compounds such as sodium 2-mercaptobenzothiazole, 1,2-bis (bromo Acetoxy) -ethane, 1,4-bis- (bromoacetoxy) -2-butene, N-bromoacetamide and other organic bromoacetates or amides
• Bactericides such as quaternary ammonium salts and algae And the like control component.
• a cationic surfactant, an anionic surfactant, a nonionic surfactant, or an amphoteric surfactant can also be blended.
• scale inhibitors such as polymers containing acrylic acid and maleic acid, organic phosphonic acids such as 2-phosphonobutane-1,2,4-tricarboxylic acid, zinc salts, polymerization Corrosion inhibitors such as phosphates, organic phosphonic acids, azole compounds, and molybdates can also be added.
• the effective chlorine concentration of the algicidal / bactericidal composition of the present invention and hypochlorous acid is determined by diethyl-p-phenylenediammonium (DPD) colorimetric method, DPD-ammonium iron (II) sulfate titration method (JIS K 0101). ) Etc., and simple analysis kits are also commercially available.
• the effective chlorine concentration measurement in the present invention was performed using a DPD-ammonium iron (II) sulfate titration method and an effective chlorine counter CL-300 (iodine coulometric titration method) manufactured by Hiranuma Sangyo Co., Ltd.
• the amount of the algicidal / bactericidal agent of the present invention to be added to the aqueous system varies depending on the scale of the aqueous system, the quality of the target aqueous system, the degree of contamination, the frequency of addition, etc. Is preferably 0.1 to 50 mg / L as the residual chlorine concentration in the water.
• the residual chlorine concentration is lower than 0.1 mg / L, the effect of the present invention cannot be expected substantially.
• the residual chlorine concentration is higher than 50 mg / L, it is not preferable in terms of economy.
• the residual chlorine concentration here means all effective chlorine concentrations remaining in water.
• the present invention also relates to a method for inhibiting the growth and / or proliferation of algae and / or bacteria in the aqueous system by adding the above-mentioned compound represented by formula (I) into the aqueous system.
• This method is particularly suitable for the control of algae and / or bacteria in aqueous systems in contact with metal parts where corrosion is not desired.
• the algicide / bactericides of the present invention are less corrosive to iron and copper even at high concentrations.
• the compound represented by formula (I) is 0.2 to 10 mg / L as a residual chlorine concentration (Cl 2 equivalent), Preferably, it is added to the aqueous system so as to be 2.5 to 5.0 mg / L.
• metal members that do not require corrosion include metal pipes and equipment that come into contact with water systems.
• the metal include iron, copper, and stainless steel.
• the residual chlorine concentration (in terms of Cl 2 ) can be measured by the above-described method for measuring effective chlorine concentration.
• Example 1 In Example 1, 6.8 g of 2-pyrrolidinone [reagent, manufactured by Kanto Chemical Co., Ltd.] was added to 100 g of chloroform [reagent, manufactured by Kanto Chemical Co., Ltd.], and trichloroisocyanuric acid [reagent, Tokyo Chemical Industry ( Co., Ltd.] 9.3 g of koji was added over 40 minutes. The resulting white slurry was filtered with suction after stirring for 6 hours. The filtrate was concentrated on a rotary evaporator and then ice-cooled to obtain 9.4 g of white crystals of N-chloro-2-pyrrolidinone (yield 98.4%, physical properties are shown below).
• Example 2 7.6 g of 2-piperidone [reagent, manufactured by Kanto Chemical Co., Ltd.] ⁇ and 42.8 g of waterpox were mixed, and 4.6 g of acetic acid [reagent, manufactured by Kanto Chemical Co., Ltd.] was added to the aqueous solution.
• Sodium hypochlorite solution with an effective chlorine concentration of 12% [effective chlorine concentration of 12%, manufactured by Yayoi Sangyo Co., Ltd.] 5.0 45.0 g was added, and an N-chloro-2-piperidone aqueous solution with an effective chlorine concentration of 5.4% 100 g of koji was prepared.
• the chlorine form was detected as bound in the DPD-iron ammonium sulfate (II) titration method.
• Example 3 7.9 g of ⁇ -caprolactam [reagent, manufactured by Kanto Chemical Co., Ltd.] was added to 100 g of chloroform, and 8.1 g of trichloroisocyanuric acid was added over 90 minutes under ice cooling. The resulting white slurry was filtered with suction after stirring for 6 hours, and the filtrate was concentrated by a rotary evaporator to obtain 10.1 g of a slightly yellow transparent oil of N-chloro- ⁇ -caprolactam (yield 97.9%, physical properties are as follows). To show).
• Example 4 8.6 g of ⁇ -heptalactam [reagent, manufactured by Tokyo Chemical Industry Co., Ltd.] was dissolved in 31.8 g of water tank instead of 2-piperidone of Example 2, and 10.0 g of ⁇ -butyrolactone was added. Except for the above, the same operation as in Example 2 was carried out to obtain 100 g of an aqueous N-chloro- ⁇ -heptalactam solution having an effective chlorine concentration of 5.4%. In this aqueous solution, the chlorine form was detected as bound in the DPD-iron ammonium sulfate (II) titration method.
• II DPD-iron ammonium sulfate
• Example 5 tetrahydro-2-pyrimidinone [reagent, manufactured by Tokyo Chemical Industry Co., Ltd.] 5.0 g-2 was added dichloromethane [reagent, manufactured by Kanto Chemical Co., Ltd.] 40.0 g, and trichloroisocyanuric acid. 8. 5 g of koji was added over 30 minutes. The resulting white slurry was stirred and filtered for 8 hours, and the filtrate was concentrated with a rotary evaporator and then ice-cooled to obtain 8.1 g of white crystals of N, N'-dichloro-tetrahydro-2-pyrimidinone (yield 96. 2%, physical properties are shown below).
• Example 6 5.6 g of white crystals of N-chloro-tetrahydro-2-pyrimidinone were obtained by performing the same operation while reducing the chlorinating agent trichloroisocyanuric acid in Example 5 to 3.9 g (yield 83). 2%, physical properties are shown below).
• Example 7 6.5 g of ethylene urea [reagent, manufactured by Tokyo Chemical Industry Co., Ltd.] was dispersed in 40 g of ethyl acetate [reagent, manufactured by Kanto Chemical Co., Inc.] to form a suspension. Dimethylhydantoin 15.5g was added over 1 hour. The resulting white slurry was filtered after stirring for 8 hours, and the filtrate was concentrated with a rotary evaporator. The precipitated white crystals were filtered and dried to obtain 3.5 g of N, N′-dichloro-2-imidazolidinone (yield) 30.1%, physical properties are shown below).
• Comparative Example 1 11.9 g of water syrup, 15.6 g of 48% by weight sodium hydroxide aqueous solution, 12.0 g of sulfamic acid cocoon, 60.0 g of sodium hypochlorite solution with an effective chlorine concentration of 12%, and 0.5 g of benzotriazole
• an algicidal / bactericidal agent containing N-chlorosulfamic acid and N, N-dichlorosulfamic acid was prepared.
• the effective chlorine concentration of this algicide / bactericidal agent was 7.2%.
• the chlorine form was detected as bound in the DPD-iron ammonium sulfate (II) titration method.
• Comparative Example 3 only a sodium hypochlorite solution having an effective chlorine concentration of 12% was used. In this solution, the chlorine form was detected as free in the DPD-iron (II) ammonium sulfate titration method.
• Test example 1 Algae killing test (green algae and cyanobacteria) Using the green alga Chlorella vulgaris C-135 (hereinafter referred to as chlorella) and the cyanobacteria Microcystis aeruginosa Lemmermann NIES-44 (hereinafter referred to as microkitis), the algicidal effect of the algicidal and bactericidal agents of Examples and Comparative Examples Evaluated. Chlorella uses a pre-cultured solution in MDM medium with an absorbance of O.D. D.
• N-chloro and N, N′-dichloro compounds of the present invention showed a high algicidal effect against microkistis, which is a cyanobacteria that constitutes the blue sea urchin and is a biological indicator. It was.
• Test Example 2 Bactericidal power test Cooling water from a cooling tower for air conditioning in Sakai Hospital was used as test water. Table 3 shows the quality of the cooling water.
• each of this cooling water was dispensed into an L-shaped test tube, and each algicidal / bactericidal agent prepared in Examples and Comparative Examples was added so as to have a predetermined concentration as an effective chlorine concentration to evaluate the efficacy.
• the test conditions were carried out by shaking culture in a constant temperature bath at 30 ° C., and measuring the number of general bacteria in the test water 1 hour and 6 hours after the addition of the drug. The results are shown in Table 4. The amount of drug added in Table 4 is shown as effective chlorine concentration.
• the N-chloro and N, N′-dichloro compounds of the present invention showed a very excellent bactericidal effect at a low concentration.
• the N-chloro compound of sulfamic acid shown in Comparative Example 1 has a very weak bactericidal effect, and after 1 hour of addition, it shows only a weaker effect than sodium hypochlorite, which is the free chlorine of Comparative Example 3. Even after the time, the addition of a low concentration showed almost no effect.
• 1-chloro-5,5-dimethylhydantoin of Comparative Example 2 also showed a certain bactericidal effect when added at a high concentration, but the effect was only low compared with the algicidal / bactericidal agent of the present invention. This also indicates that the N-chloro and N, N'-dichloro compounds of the present invention exhibit a bactericidal effect quickly even at low concentrations, even though they are bound N-chloro compounds.
• Test Example 3 Metal Corrosiveness Stainless steel SUS304 (single side # 400 polished finish, 2.5 ⁇ 15 ⁇ 50 mm), iron (SS-400, 2.3 ⁇ 15 ⁇ 30 mm) and copper (C122OP) in a glass container with a lid , 2.0 ⁇ 20 ⁇ 50 mm), a predetermined amount of clean water (Iwata City Shizuoka City water) is measured to a position where a gas phase portion and a solution immersion portion can be formed. 3.
• the algicidal and bactericidal agents of Comparative Examples 1 and 3 were added so that the effective chlorine concentration was 2.5 mg / L and 5 mg / L, and the degree of corrosion of the test piece was observed at 30 ° C.
• the test solution is changed once a week, and after 8 weeks, the test piece is taken out, and the degree of corrosion (gmd; g / m 2 ⁇ day) is obtained.
• the degree of corrosion of each algicide / bactericide was evaluated according to the criteria shown in Table 6 below with respect to the degree of corrosion in the non-agent-added section (only clean water). The results are shown in Table 7 in combination with symbols.

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• 2011
  • 2011-01-07 JP JP2011002059A patent/JP5643117B2/ja active Active
  • 2011-12-26 KR KR20137016670A patent/KR20130141624A/ko not_active Application Discontinuation
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