WO2015093519A1 - Composition désinfectante - Google Patents

Composition désinfectante Download PDF

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Publication number
WO2015093519A1
WO2015093519A1 PCT/JP2014/083385 JP2014083385W WO2015093519A1 WO 2015093519 A1 WO2015093519 A1 WO 2015093519A1 JP 2014083385 W JP2014083385 W JP 2014083385W WO 2015093519 A1 WO2015093519 A1 WO 2015093519A1
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WO
WIPO (PCT)
Prior art keywords
component
group
methyl
bromo
formula
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PCT/JP2014/083385
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English (en)
Japanese (ja)
Inventor
陽 濱川
新井　重文
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日本曹達株式会社
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Publication date
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Priority to JP2015553578A priority Critical patent/JP6078170B2/ja
Publication of WO2015093519A1 publication Critical patent/WO2015093519A1/fr

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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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to a fungicide composition. More specifically, the present invention relates to a fungicide composition used for controlling bacteria, molds, yeasts, algae and the like.
  • This application claims priority based on Japanese Patent Application No. 2013-263707 for which it applied to Japan on December 20, 2013, and uses the content here.
  • Microbicidal compounds having a 4-isothiazolin-3-one skeleton are collectively referred to as isothiazoline fungicides and are used to control harmful microorganisms such as bacteria, fungi, yeasts and algae.
  • isothiazoline fungicides include 2-methyl-4-isothiazolin-3-one (hereinafter sometimes abbreviated as H-MIT), 5-chloro-2-methyl-4-isothiazolin-3-one ( Hereinafter abbreviated as Cl-MIT), 1,2-benzisothiazolin-3-one (hereinafter sometimes abbreviated as BIT), 2-n-octyl-4-isothiazolin-3-one, 4 , 5-dichloro-2-octyl-4-isothiazolin-3-one, 2-n-butyl-1,2-benzisothiazolin-3-one, 2-methyl-4,5-trimethylene-4-isothiazoline-3- ON (hereinafter sometimes abbreviated as MTI
  • Patent Document 1 proposes a combination of 2-methyl-4-isothiazolin-3-one and 2-bromo-2-nitro-1,3-propanediol.
  • Patent Document 2 proposes a combination of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-bromo-2-nitro-1,3-propanediol.
  • Patent Document 3 describes an antibacterial N-formal such as hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine and a bactericide such as 2-n-octyl-4-isothiazolin-3-one. Proposes a combination.
  • An object of the present invention is to provide a new fungicide composition using 2-methyl-4,5-trimethylene-4-isothiazolin-3-one.
  • Component (A) 2-methyl-4,5-trimethylene-4-isothiazolin-3-one
  • Component (B) compound represented by formula (1), hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine, didecyldimethylammonium chloride, benzalkonium chloride, zinc pyrithione, polyhexa
  • a disinfectant composition comprising methyleneguanidine hydrochloride and at least one selected from the group consisting of polyhexamethylene biguanide hydrochloride.
  • X 1 and X 2 each independently represent a bromo group, a nitro group or a cyano group, provided that at least one of X 1 and X 2 is a bromo group.
  • R 1 is methyl.
  • R 2 represents a methyl group, a hydroxymethyl group or an aminocarbonyl group.
  • the compound represented by the formula (1) is 2-bromo-2-nitropropane-1,3-diol, 2,2-dibromo-2-nitroethanol, or 2,2-dibromo-3-nitrilo
  • Component (B) is hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine, 2-bromo-2-nitropropane-1,3-diol, 2,2-dibromo- 2-nitroethanol, 2,2-dibromo-3-nitrilopropionamide, didecyldimethylammonium chloride, benzalkonium chloride, zinc pyrithione, polyhexamethyleneguanidine hydrochloride, or polyhexamethylenebiguanide hydrochloride [3] The disinfectant composition described in 1.
  • bactericidal composition having a further excellent bactericidal effect Things are provided.
  • the fungicide composition of the present invention comprises component (A): 2-methyl-4,5-trimethylene-4-isothiazolin-3-one, component (B): a compound represented by formula (1), hexahydro- Selected from the group consisting of 1,3,5-tris (2-hydroxyethyl) -s-triazine, didecyldimethylammonium chloride, benzalkonium chloride, zinc pyrithione, polyhexamethylene guanidine hydrochloride, and polyhexamethylene biguanide hydrochloride And at least one of the above.
  • X 1 and X 2 each independently represent a bromo group, a nitro group or a cyano group, provided that at least one of X 1 and X 2 is a bromo group.
  • R 1 is methyl.
  • R 2 represents a methyl group, a hydroxymethyl group or an aminocarbonyl group.
  • Component (A) 2-methyl-4,5-trimethylene-4-isothiazolin-3-one is a compound represented by the formula (2).
  • One of the components (B), hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine, is a compound represented by the formula (3).
  • Didecyldimethylammonium chloride which is one of the components (B), is a compound represented by the formula (4).
  • Benzalkonium chloride which is one of the components (B), is a compound represented by the formula (5).
  • Zinc pyrithione which is one of the components (B), is a compound represented by the formula (6).
  • Polyhexamethylene guanidine hydrochloride which is one of the components (B), is a compound represented by the formula (7).
  • Polyhexamethylene biguanide hydrochloride which is one of the components (B), is a compound represented by the formula (8).
  • Examples of the compound represented by the formula (1) which is one of the components (B) include 2-bromo-2-nitropropane-1,3-diol, 2,2-dibromo-2-nitroethanol, and 2,2 -Dibromo-3-nitrilopropionamide is preferred.
  • 2-bromo-2-nitropropane-1,3-diol is a compound represented by the formula (1a)
  • 2,2-dibromo-2-nitroethanol is a compound represented by the formula (1b
  • 2,2-Dibromo-3-nitrilopropionamide is a compound represented by the formula (1c).
  • component (B) in the fungicide composition of the present invention is not particularly limited with respect to component (A), and may vary depending on the target fungus, but component (A) 100
  • the amount is preferably 1 to 10,000 parts by mass, more preferably 2 to 900 parts by mass with respect to parts by mass.
  • the amount of the component (B) is preferably 10 150 parts by mass.
  • the amount of component (B) is preferably 150 with respect to 100 parts by mass of component (A). ⁇ 900 parts by mass.
  • the amount of component (B) is preferably based on 100 parts by mass of component (A) 20 to 500 parts by mass.
  • component (B) is at least one selected from the group consisting of polyhexamethylene guanidine hydrochloride and polyhexamethylene biguanide hydrochloride
  • the amount of component (B) is based on 100 parts by mass of component (A)
  • the amount is preferably 2 to 300 parts by mass.
  • component (B) is zinc pyrithione
  • the amount of component (B) is preferably 5 to 150 parts by mass with respect to 100 parts by mass of component (A).
  • component (B) When component (B) is 2-bromo-2-nitropropane-1,3-diol, the amount of component (B) is preferably 20 to 30 parts by mass with respect to 100 parts by mass of component (A). It is. When component (B) is 2,2-dibromo-2-nitroethanol, the amount of component (B) is preferably 20 to 80 parts by mass with respect to 100 parts by mass of component (A). When component (B) is 2,2-dibromo-3-nitrilopropionamide, the amount of component (B) is preferably 10 to 150 parts by mass with respect to 100 parts by mass of component (A).
  • the amount of component (B) is preferably 30 to 80 parts by mass with respect to 100 parts by mass of component (A).
  • the amount of the component (B) is preferably 20 to 500 parts by mass with respect to 100 parts by mass of the component (A).
  • the amount of component (B) is preferably 2 to 300 parts by mass with respect to 100 parts by mass of component (A).
  • the amount of component (B) is preferably 3 to 150 parts by mass with respect to 100 parts by mass of component (A).
  • the dosage form of the fungicide composition of the present invention is not particularly limited, but is preferably liquid at room temperature.
  • Specific examples of the liquid disinfectant composition include an aqueous solvent, a suspending agent, an emulsion, an emulsion, and a suspoemulsion. These dosage forms can be selected according to the physical properties of the sterilizing component contained and the application of the sterilizing composition.
  • the fungicide composition of the present invention may contain components such as a solvent and a surfactant as necessary.
  • Organic solvents include nonpolar solvents such as toluene, xylene, and methylnaphthalene; lower alcohols such as ethanol and isopropanol; glycol solvents such as ethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, and glycerin; acetone, methyl ethyl ketone, and cyclohexanone Ketone solvents such as dimethylformamide, propylene carbonate, dimethyl sulfoxide, acetonitrile, and polar solvents such as N-methylpyrrolidone.
  • nonpolar solvents such as toluene, xylene, and methylnaphthalene
  • lower alcohols such as ethanol and isopropanol
  • glycol solvents such as ethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, and glycerin
  • surfactant examples include cationic surfactants such as alkyltrimethylammonium salt, dialkyldimethylammonium salt, alkylbenzyldimethylammonium salt, alkylpyridinium salt, and polyhexamethylene biguanide.
  • Nonionic surfactants such as ether, polyoxyalkylene alkyl phenyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene castor oil, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester; alkylmethylamine oxide, alkyl Examples
  • the biocidal composition of the present invention may contain other biocidal active ingredients.
  • the biocidal active ingredient include those having activities such as microbicidal properties, antiseptic properties, fungicidal properties, algal-proofing properties, ant-proofing properties, and insecticidal properties.
  • the fungicide composition of the present invention has a wide range of control targets and can be stored for a long period of time, or a further synergistic effect may be obtained. is there.
  • biocidal active ingredients examples include 2,4,5,6-tetrachloroisophthalonitrile, 5-chloro-2,4,6-trifluoroisophthalonitrile, 5-chloro-2,4-difluoro- Isophthalonitrile compounds such as 6-methoxyisophthalonitrile; pyridine compounds such as 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine; pyrithione compounds such as zinc pyrithione, sodium pyrithione and copper pyrithione Benzimidazole compounds such as methyl benzimidazol-2-ylcarbamate, methyl 1-butylcarbamoylbenzimidazol-2-ylcarbamate, 2- (thiazol-4-yl) benzimidazole; carbamates such as zinc dimethyldithiocarbamate Compounds: Imazaril, Tebucona Azole compounds such as benzene, hexaconazole and
  • the bactericidal effect of the chemical solution was evaluated by the following test.
  • Pseudomonas aeruginosa Pseudomonas aeruginosa NBRC13275 strain
  • a nutrient broth ordinary bouillon “Eiken” manufactured by Eiken Chemical Co., Ltd.
  • the obtained culture solution was diluted 100 times with a fresh nutrient broth liquid medium to obtain a bacterial solution.
  • Each 40 ⁇ L of the drug solution to be tested was dropped on a 96-well microplate.
  • Each 60 ⁇ L of the bacterial solution was added to the chemical solution.
  • the microplate was allowed to stand in the dark at 31 ° C. for 24 hours and cultured.
  • the presence or absence of bacterial growth was examined with the naked eye. A group in which no growth was observed was determined as a group in which growth inhibition was observed.
  • Example 2-Methyl-4,5-trimethylene-4-isothiazolin-3-one (MTI, manufactured by Nippon Soda Co., Ltd.) was dissolved in dimethyl sulfoxide to obtain an MTI solution.
  • MTI Methyl-4,5-trimethylene-4-isothiazolin-3-one
  • HHT Hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine
  • HHT triazine preservative “Bestside-1087T” manufactured by Nippon Soda Co., Ltd.
  • 2-Bromo-2-nitropropane-1,3-diol (BNPD, manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in dimethyl sulfoxide to obtain a BNPD solution.
  • DBNE 2,2-Dibromo-2-nitroethanol
  • DBNE-75P 2,2-Dibromo-3-nitrilopropionamide
  • DBNPA didecyldimethylammonium chloride
  • DDAC didecyldimethylammonium chloride
  • Benzalkonium chloride (BEC, manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in dimethyl sulfoxide to obtain a BEC solution.
  • Zinc pyrithione (ZPT, manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in dimethyl sulfoxide to obtain a ZPT solution.
  • Polyhexamethylene guanidine hydrochloride (PHMG, Nippon Soda Co., Ltd.) was dissolved in purified water to obtain a PHMG solution.
  • Polyhexamethylene biguanide hydrochloride (PHMB, Nippon Soda Co., Ltd.) was dissolved in purified water to obtain a PHMB solution.
  • MIC with MTI alone is 50 ppm
  • MIC with HHT alone is 200 ppm
  • MIC with BNPD alone is 6.25 ppm
  • MIC with DBNE alone is 6.25 ppm
  • MIC with DBNPA alone is 12.5 ppm
  • DDAC alone The MIC was 12.5 ppm
  • the MIC with BEC alone was 50 ppm
  • the MIC with ZPT alone was 25 ppm
  • the MIC with PHMG alone was 12.5 ppm
  • the MIC with PHMB alone was 12.5 ppm.
  • the FIC index (Fractional Inhibitory Concentration index) was calculated by the following formula.
  • FIC index a / a0 + b / b0 a0: MIC with component A alone b0: MIC with component B alone a: MIC of A component when A component and B component are used together b: MIC of B component when A component and B component are used together
  • the FIC index represents the effect of the combined use of the A component and the B component. When the FIC index is 1, it indicates that there is an additive effect by the combined use of the A component and the B component. When the FIC index is greater than 1, it indicates that there is an antagonistic effect by the combined use of the A component and the B component. When the FIC index is less than 1, it indicates that the combination of the A component and the B component has a synergistic effect. Tables 10 to 18 show MICs when MTI is used in combination with other drugs.
  • the fungicide composition of the present invention comprises MTI, hexahydro-1,3,5-tris (2-hydroxyethyl) -s-triazine, didecyldimethylammonium chloride, benzalkonium chloride, zinc pyrithione,
  • the bactericidal property is improved with a synergistic action by the combined use with polyhexamethylene guanidine hydrochloride, polyhexamethylene biguanide hydrochloride, or a compound represented by the formula (1).
  • the bactericidal composition of the present invention has a sufficient bactericidal effect.
  • a disinfectant composition can be provided.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition désinfectante qui comprend un composant (A) : 2-méthyl-4,5-triméthylène-4-isothiazoline-3-one, et un composant (B) : au moins un composant choisi dans l'ensemble consistant en un composé représenté par la formule (1), l'hexahydro-1,3,5-tris(2-hydroxyéthyl)-s-triazine, le chlorure de didécyldiméthylammonium, chlorure de benzalconium, le zinc pyrithione, le chlorhydrate de polyhexaméthylène guanidine et le chlorhydrate de polyhexaméthylène biguanide. (Dans la formule (1), X1 et X2 représentent chacun indépendamment un groupe bromo, un groupe nitro ou un groupe cyano, sous réserve qu'au moins un parmi X1 et X2 représente un groupe bromo. R1 représente un groupe méthyle, un groupe hydroxyméthyle ou un groupe bromo. R2 représente un groupe méthyle, un groupe hydroxyméthyle ou un groupe aminocarbonyle).
PCT/JP2014/083385 2013-12-20 2014-12-17 Composition désinfectante WO2015093519A1 (fr)

Priority Applications (1)

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JP2015553578A JP6078170B2 (ja) 2013-12-20 2014-12-17 殺菌剤組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013263707 2013-12-20
JP2013-263707 2013-12-20

Publications (1)

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WO2015093519A1 true WO2015093519A1 (fr) 2015-06-25

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017057194A (ja) * 2015-09-17 2017-03-23 住化エンバイロメンタルサイエンス株式会社 アレルゲン低減化および抗菌組成物
JP2020090545A (ja) * 2015-07-30 2020-06-11 住化エンバイロメンタルサイエンス株式会社 木材用抗菌組成物
EP4003013A4 (fr) * 2019-07-31 2022-09-07 Siemens Healthcare Diagnostics, Inc. Formulations de biocide améliorées pour la conservation d'un capteur de détection d'analyte (s) et procédé (s) d'utilisation et de celle-ci

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JPH0733614A (ja) * 1993-07-20 1995-02-03 Katayama Chem Works Co Ltd 工業用殺菌・静菌剤
JPH0769817A (ja) * 1990-04-27 1995-03-14 Zeneca Ltd 殺微生物組成物及びその使用方法
JPH0977616A (ja) * 1995-09-14 1997-03-25 Kurita Water Ind Ltd 工業用殺菌剤組成物
JPH09278611A (ja) * 1995-12-23 1997-10-28 Riedel De Haen Ag イソチアゾリノン誘導体および錯化剤を含む防腐剤
JPH1135410A (ja) * 1997-04-30 1999-02-09 Nalco Chem Co 過酢酸及び非酸化性殺生剤を包含する微生物の成長を抑制するための組成物及び方法

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GB2341092B (en) * 1998-09-07 2000-12-06 Macgregor Keith Martin Composition for the removal of biological and organic substances
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JP2002193707A (ja) * 2000-12-22 2002-07-10 Mitsubishi Gas Chem Co Inc 多機能型水処理剤
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Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0769817A (ja) * 1990-04-27 1995-03-14 Zeneca Ltd 殺微生物組成物及びその使用方法
JPH04295404A (ja) * 1990-12-20 1992-10-20 Imperial Chem Ind Plc <Ici> 抗菌組成物及びその使用
JPH0733614A (ja) * 1993-07-20 1995-02-03 Katayama Chem Works Co Ltd 工業用殺菌・静菌剤
JPH0977616A (ja) * 1995-09-14 1997-03-25 Kurita Water Ind Ltd 工業用殺菌剤組成物
JPH09278611A (ja) * 1995-12-23 1997-10-28 Riedel De Haen Ag イソチアゾリノン誘導体および錯化剤を含む防腐剤
JPH1135410A (ja) * 1997-04-30 1999-02-09 Nalco Chem Co 過酢酸及び非酸化性殺生剤を包含する微生物の成長を抑制するための組成物及び方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020090545A (ja) * 2015-07-30 2020-06-11 住化エンバイロメンタルサイエンス株式会社 木材用抗菌組成物
JP2017057194A (ja) * 2015-09-17 2017-03-23 住化エンバイロメンタルサイエンス株式会社 アレルゲン低減化および抗菌組成物
JP7007540B2 (ja) 2015-09-17 2022-02-10 住化エンバイロメンタルサイエンス株式会社 アレルゲン低減化および抗菌組成物
EP4003013A4 (fr) * 2019-07-31 2022-09-07 Siemens Healthcare Diagnostics, Inc. Formulations de biocide améliorées pour la conservation d'un capteur de détection d'analyte (s) et procédé (s) d'utilisation et de celle-ci

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JP6078170B2 (ja) 2017-02-08

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