Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B50/00—Formazane dyes; Tetrazolium dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B50/00—Formazane dyes; Tetrazolium dyes
  • C09B50/02—Tetrazolium dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/006—Preparation of organic pigments
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
  • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
  • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
  • C12N1/20—Bacteria; Culture media therefor
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
  • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
  • C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
  • C12Q1/04—Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor
• • G—PHYSICS
  • G01—MEASURING; TESTING
  • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
  • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
  • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
  • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
• • G—PHYSICS
  • G01—MEASURING; TESTING
  • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
  • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
  • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
  • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
  • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
• • G—PHYSICS
  • G01—MEASURING; TESTING
  • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
  • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
  • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
  • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
  • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
  • G01N21/80—Indicating pH value
• • 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
  • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
  • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
  • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

• the present disclosure provides compounds, their tautomers or their salts with alkali metals or organic bases, decolorizing compositions, dyes, media compositions for detecting enterohemorrhagic E. coli, and intestinal bleeding in specimens.
• the present invention relates to a method for detecting E.coli.
• JP-A-11-193266 discloses a formazan dye compound having a structure in which a benzene ring is directly linked to an azo group, which is used as a silver halide photographic light-sensitive material.
• pigment compounds are required to develop good color even when used in small amounts. Since the formazan dye compound described in JP-A-11-193266 does not have good color development properties, it needs to be used in a large amount in order to fully exhibit its function as a dye.
• a dye compound is added to the enterohemorrhagic E. coli detection medium in order to enhance the visibility of the enterohemorrhagic E. coli contained in the sample.
• a sample for confirming the presence of enterohemorrhagic E. coli is usually mixed with a plurality of bacteria, so it is not easy to accurately detect only enterohemorrhagic E. coli. Therefore, colonies of bacteria other than enterohemorrhagic E. coli are colored to enhance the visibility of enterohemorrhagic E. coli.
• O157 one of the representative enterohemorrhagic Escherichia coli, is a bacterium that does not decompose D-sorbitol, a type of sugar.
• colonies of bacteria that decompose D-sorbitol are contained in the medium due to a decrease in pH due to the influence of organic acids produced by the decomposition of D-sorbitol. Since the neutral red of the pH indicator used is pink, it is possible to distinguish it from O157 colonies. However, with such a method, it is difficult to distinguish enterohemorrhagic E. coli when bacteria other than enterohemorrhagic E. coli are present in large amounts.
• the problem to be solved by one embodiment of the present disclosure is to provide a medium composition for detecting enterohemorrhagic E. coli, which enables good visualization of enterohemorrhagic E. coli even with a small amount of dye compound used.
• a problem to be solved by another embodiment of the present disclosure is to provide a method for detecting enterohemorrhagic E. coli in a specimen using the medium composition for detecting enterohemorrhagic E. coli.
• Another problem to be solved by other embodiments of the present disclosure is to provide novel compounds, their tautomers, or their salts with alkali metals or organic bases.
• Another problem to be solved by another embodiment of the present disclosure is to provide a coloring and decoloring composition and a dyed article containing the above compound and the like.
• Means for solving the above problems include the following aspects. ⁇ 1> a compound represented by the following formula (1) or a compound represented by the following formula (2); water and, A composition for medium for detecting enterohemorrhagic Escherichia coli containing.
• Ar 1 and Ar 2 each independently represent a heterocyclic group, and R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group, or a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• ⁇ 5> culturing a specimen in a medium containing the enterohemorrhagic E. coli detection medium composition according to any one of ⁇ 1> to ⁇ 4>, and detecting the presence or absence of enterohemorrhagic E. coli, A method for detecting enterohemorrhagic E. coli in a specimen.
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom or an alkyl group. , represents an aromatic ring group or a heterocyclic group.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• Ar 1 and Ar 2 each independently represent a group represented by formula (A-1) below, a group represented by formula (A-2) below, or a group represented by formula (A-2) below.
• (A-3) represents a group represented by the following formula (A-4) or a group represented by the following formula (A-5)
• R is an alkyl group, an aromatic ring group, a hetero represents a cyclic group, an acyl group or a carbamoyl group
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• R 1A represents a hydrogen atom, an alkyl group, a phenyl group, an acyl group or an alkoxycarbonyl group
• R 2A represents a hydrogen atom, a cyano group, a carbamoyl group or an alkylsulfonyl group
• R 3A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group
• R 4A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group.
• R 5A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• R 6A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• * represents a bonding position.
• a medium composition for detecting enterohemorrhagic E. coli which allows the enterohemorrhagic E. coli to be well visualized by using even a small amount of dye compound.
• a method for detecting enterohemorrhagic E. coli in a specimen using the medium composition for detecting enterohemorrhagic E. coli can be provided.
• novel compounds, their tautomers, or their salts with alkali metals or organic bases can be provided.
• a color-changing composition and a dyed article containing the above compounds can be provided.
• a numerical range indicated using “to” means a range including the numerical values before and after "to” as lower and upper limits, respectively.
• upper or lower limits described in a certain numerical range may be replaced with upper or lower limits of other numerical ranges described step by step.
• upper or lower limits described in a certain numerical range may be replaced with values shown in Examples.
• the amount of each component in the composition when referring to the amount of each component in the composition, if there are multiple substances corresponding to each component in the composition, unless otherwise specified, the amount of the multiple components present in the composition is means total volume.
• alkyl group includes not only alkyl groups having no substituents (also referred to as “unsubstituted alkyl groups”) but also alkyl groups having substituents (also referred to as "substituted alkyl groups”). It includes.
• n- means normal and "t-" means tertiary.
• process includes not only an independent process but also a process that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved. .
• the medium composition for detecting enterohemorrhagic E. coli (hereinafter also simply referred to as "medium composition") according to the present disclosure is a composition used in a medium for detecting enterohemorrhagic E. coli, and has the following formula (1 ) or the compound represented by the following formula (2), and water.
• the compound represented by the following formula (2) is an oxidant of the compound represented by the following formula (1).
• Ar 1 and Ar 2 each independently represent a heterocyclic group, and R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group, or a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• the culture medium composition according to the present disclosure allows good visualization of enterohemorrhagic E. coli even when the amount of the pigment compound used is small. Although it is not clear why the culture medium composition according to the present disclosure can exhibit such effects, the present inventors speculate as follows. However, the following assumptions are not to be construed as limiting the composition for medium according to the present disclosure, but are explained as an example.
• the compound represented by Formula (1) and the compound represented by Formula (2) are compounds that develop and decolor due to oxidation-reduction reactions.
• the compound represented by formula (2) is an oxidant of the compound represented by formula (1). In the state of the compound represented by formula (1), it is colored, and when the compound represented by formula (1) is oxidized and becomes the state of the compound represented by formula (2), the color disappears. Further, when the compound represented by the formula (2) is reduced to the state of the compound represented by the formula (1), it exhibits a color.
• the medium composition according to the present disclosure utilizes the reducing power of enterohemorrhagic E. coli to reduce the compound represented by formula (2), thereby coloring enterohemorrhagic E. coli.
• enterohemorrhagic Escherichia coli Since enterohemorrhagic Escherichia coli has a strong reducing power, it is considered that it can satisfactorily reduce the compound represented by formula (2) contained in the medium composition.
• the medium composition according to the present disclosure contains the compound represented by formula (1), after oxidizing the compound represented by formula (1), a sample that may contain enterohemorrhagic E. coli is Enterohemorrhagic E. coli can be colored by inoculating the medium.
• the medium composition according to the present disclosure contains the compound represented by the formula (1) or the compound represented by the formula (2) as a dye compound used for detecting enterohemorrhagic E. coli. Enterohemorrhagic E. coli can be well visualized even when used in small amounts.
• a heteroatom into the formazan dye compound
• the polarization of the formazan dye compound was increased, and the gram extinction coefficient of the formazan dye compound was improved. be done.
• the present inventors have found that formazan dye compounds containing a five-membered heterocycle have high color development when reduced compared to conventional formazan dye compounds, that is, formazan dye compounds based on a benzene ring. I'm sure.
• introduction of a heteroatom into the formazan dye compound improved the hydrophilicity and improved the color development in water, thereby enabling good visual recognition of enterohemorrhagic E. coli.
• the medium composition according to the present disclosure can be used regardless of the type of enterohemorrhagic Escherichia coli.
• Enterohemorrhagic E. coli is pathogenic E. coli that produces a toxin called verotoxin.
• Specific examples of enterohemorrhagic Escherichia coli include, but are not limited to, O157, O26, O111, and the like.
• Ar 1 and Ar 2 each independently represent a heterocyclic group.
• the heterocyclic group represented by Ar 1 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the heterocyclic group represented by Ar 2 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by Ar 1 is preferably 1-3, more preferably 1 or 2.
• the number of heteroatoms in the heterocyclic group represented by Ar 2 is preferably 1-3, more preferably 1 or 2.
• the heterocyclic group represented by Ar 1 is preferably a heterocyclic group containing a 5-membered ring, more preferably a 5-membered heterocyclic group.
• the heterocyclic group represented by Ar 2 is preferably a heterocyclic group containing a 5-membered ring, more preferably a 5-membered heterocyclic group.
• the heterocyclic group represented by Ar 1 is a heterocyclic group containing one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring, and is a heterocyclic ring containing a 5-membered heterocyclic ring.
• the heterocyclic group represented by Ar 2 is a heterocyclic group containing one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring, and is a heterocyclic ring containing a 5-membered heterocyclic ring.
• the heterocyclic group represented by Ar 1 and the heterocyclic group represented by Ar 2 may be the same or different.
• the hue can be adjusted by changing the types of the heterocyclic group represented by Ar 1 and the heterocyclic group represented by Ar 2 and the combination thereof.
• the heterocyclic group represented by Ar 1 and the heterocyclic group represented by Ar 2 may be unsubstituted or may have a substituent.
• Each of the heterocyclic group represented by Ar 1 and the heterocyclic group represented by Ar 2 may have one or more substituents, and two or more substituents may be the same or different.
• substituents include halogen groups, hydroxy groups, alkyl groups, cycloalkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heterocyclic groups (heterocyclic groups), alkoxy groups, aryloxy groups, heterocyclic oxy group, sulfo group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carboxy group, carbamoyl group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, cyano group, nitro group, amino groups (including anilino groups), acylamino groups, alkoxycarbonylamino groups, carbamoylamino groups, aryloxycarbonylamino groups, sulfamoylamino groups, alkylsulfonylamino groups, arylsulfonylamino groups, mer
• the substituents include, for example, halogen groups (eg, fluoro, chloro, bromo, and iodo groups), alkyl groups (1 to 10, preferably 1 to 6 carbon straight-chain, branched or cyclic alkyl groups having atoms; for example, methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, 2-chloroethyl, 2-cyanoethyl, 2-ethylhexyl, cyclopropyl, and cyclopentyl) , alkenyl groups (linear, branched or cyclic alkenyl groups having 2 to 10, preferably 2 to 6 carbon atoms; for example, vinyl, allyl, prenyl, and cyclopenten-1-yl), alkynyl groups ( alkynyl groups having 2 to 10, preferably 2 to 6 carbon atoms; e
• halogen groups eg, fluor
• heterocyclic oxy group (heterocyclic oxy group having 1 to 12, preferably 2 to 6 carbon atoms; for example, 1-phenyltetrazol-5-oxy-2-tetrahydropyranyloxy), acyloxy group ( acyloxy groups having 1 to 12 carbon atoms, preferably 1 to 8 carbon atoms; carbamoyloxy groups having to 10, preferably 1 to 6 carbon atoms; for example, N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy, morpholinocarbonyloxy, and N,N-octylcarbamoyloxy ), alkoxycarbonyloxy groups (alkoxycarbonyloxy groups having 2 to 10, preferably 2 to 6 carbon atoms; for example, methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, and n-octyl oxycarbonyloxy), aryloxycarbonyloxy groups (
• Aryloxycarbonylamino groups (aryloxycarbonylamino groups having 7 to 12, preferably 7 to 9 carbon atoms; for example, phenoxycarbonylamino, p-chlorophenoxycarbonylamino, and 4-methoxyphenoxycarbonylamino ), sulfamoylamino groups (sulfamoylamino groups having 0 to 10, preferably 0 to 6 carbon atoms; for example, sulfamoylamino, N,N-dimethylaminosulfonylamino, and N -(2-hydroxyethyl)sulfamoylamino), alkylsulfonylamino groups (alkylsulfonylamino groups having 1 to 10, preferably 1 to 6 carbon atoms; for example, methylsulfonylamino and butylsulfonyl amino), arylsulfonylamino groups (arylsulfonylamino groups having 6
• Alkoxycarbonyl groups (alkoxycarbonyl groups having 2 to 10, preferably 2 to 6 carbon atoms; for example, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, and isobutyloxycarbonyl), aryloxycarbonyl groups ( aryloxycarbonyl groups having 7 to 12, preferably 7 to 9 carbon atoms; for example, phenoxycarbonyl-2-chlorophenoxycarbonyl, 3-nitrophenoxycarbonyl and 4-t-butylphenoxycarbonyl), Carbamoyl groups (carbamoyl groups having 1 to 10, preferably 1 to 6 carbon atoms; for example, carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-(2-hydroxyethyl)carbamoyl, and N-(methylsulfonyl)carbamoyl), aryl azo groups (aryl azo groups having 6 to 12, preferably
• these groups are groups that can be further substituted, these groups can further contain substituents, and the substituents include the heterocyclic group represented by Ar 1 or the heterocyclic group represented by Ar 2 Groups having the same meanings as those described as preferred substituents of the groups are preferably mentioned. When these groups are substituted with two or more substituents, these substituents may be the same or different.
• the substituent of the heterocyclic group represented by Ar 1 is preferably at least one selected from the group consisting of an alkyl group, an aromatic ring group, a heterocyclic group, a carbamoyl group, an alkylthio group, and an arylthio group, and an alkyl group, At least one selected from the group consisting of a carbamoyl group and an alkylthio group is more preferred.
• the substituent of the heterocyclic group represented by Ar 2 is preferably at least one selected from the group consisting of an alkyl group, an aromatic ring group, a heterocyclic group, a carbamoyl group, an alkylthio group, and an arylthio group. At least one selected from the group consisting of a carbamoyl group and an alkylthio group is more preferred.
• R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group, or a carbamoyl group.
• R is preferably an alkyl group or a heterocyclic group.
• the alkyl group represented by R may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by R is preferably, for example, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group.
• the aromatic ring group represented by R may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by R is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by R is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group represented by R may or may not have a substituent.
• the substituent is preferably, for example, a 4-pyridyl group or a 2-furyl group.
• the heterocyclic group represented by R is preferably a 5- or 6-membered ring.
• the heterocyclic group represented by R is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by R is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• the acyl group represented by R is preferably an acyl group having 2 to 30 carbon atoms, more preferably an acyl group having 2 to 15 carbon atoms.
• the acyl group represented by R is preferably, for example, an acetyl group or a pivaloyl group.
• the carbamoyl group represented by R may or may not have a substituent.
• the carbamoyl group represented by R is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• X 1 ⁇ in formula (2) is preferably a chloride ion or an acetate ion.
• the compound represented by formula (1) is preferably a compound represented by formula (3) below, a tautomer thereof, or a salt thereof with an alkali metal or an organic base.
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• X 1 and X 2 may be the same or different.
• X 1 and X 2 are each independently preferably -S- or -N(-Z 1 )-.
• Z 1 in -N(-Z 1 )- is preferably an alkyl group, an aromatic ring group, or a heterocyclic group.
• the alkyl group represented by Z 1 may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by Z 1 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by Z 1 is preferably, for example, a methyl group, an ethyl group, or a t-butyl group.
• the aromatic ring group represented by Z 1 may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by Z 1 is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by Z 1 is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group represented by Z 1 may or may not have a substituent.
• the substituent is preferably, for example, a 2-pyridyl group or a 2-pyrimidyl group.
• the heterocyclic group represented by Z 1 is preferably a 5- or 6-membered ring.
• the heterocyclic group represented by Z 1 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by Z 1 is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• Y 1 , Y 2 , Y 3 and Y 4 may be the same or different.
• the alkyl group represented by Z2 may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by Z 2 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by Z 2 is preferably, for example, a methyl group, an ethyl group, or a t-butyl group.
• the aromatic ring group represented by Z2 may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by Z 2 is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by Z 2 is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group represented by Z2 may or may not have a substituent.
• the substituent is preferably an alkyl group, an alkylthio group, or an alkoxy group, for example.
• the heterocyclic group represented by Z2 is preferably a 5- or 6-membered ring.
• the heterocyclic group represented by Z2 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by Z 2 is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• the acyl group represented by Z 2 is preferably an acyl group having 2 to 30 carbon atoms, more preferably an acyl group having 2 to 15 carbon atoms.
• the acyl group represented by Z2 is preferably, for example, an acetyl group or a pivaloyl group.
• the carbamoyl group represented by Z2 may or may not have a substituent.
• the carbamoyl group represented by Z 2 is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by Z 2 is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• the alkylthio group represented by Z 2 is preferably an alkylthio group having 1 to 12 carbon atoms in the alkyl moiety.
• the alkylthio group represented by Z2 is preferably, for example, a methylthio group or an ethylthio group.
• R 1 and R 2 each independently represent an alkyl group, an aromatic ring group, a heterocyclic group, a carbamoyl group, an alkylthio group or an arylthio group.
• R 1 and R 2 may be the same or different.
• R 1 and R 2 are each independently preferably an alkyl group.
• the alkyl group for R 1 and R 2 may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group for R 1 and R 2 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group for R 1 and R 2 is preferably, for example, a methyl group, an ethyl group, or a t-butyl group.
• the aromatic ring groups for R 1 and R 2 may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group for R 1 and R 2 is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group for R 1 and R 2 is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group for R 1 and R 2 may or may not have a substituent.
• the substituent is preferably, for example, a methoxy group or a dimethylamino group.
• the heterocyclic group for R 1 and R 2 is preferably a 5- or 6-membered ring.
• the heterocyclic group for R 1 and R 2 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group in R 1 and R 2 is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• the carbamoyl groups for R 1 and R 2 may or may not have a substituent.
• the carbamoyl group for R 1 and R 2 is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group for R 1 and R 2 is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• the alkylthio group for R 1 and R 2 is preferably an alkylthio group having 1 to 12 carbon atoms in the alkyl moiety.
• the alkylthio group for R 1 and R 2 is preferably, for example, a methylthio group or an ethylthio group.
• the arylthio group for R 1 and R 2 is preferably an arylthio group having 6 to 30 carbon atoms in the aryl moiety.
• the arylthio group for R 1 and R 2 is preferably, for example, a phenylthio group.
• R 1 and Z 2 may combine to form a ring.
• the ring formed may be a saturated ring or an unsaturated ring.
• the ring to be formed is preferably, for example, a benzene ring or a naphthalene ring.
• R 2 and Z 2 may combine to form a ring.
• the ring formed may be a saturated ring or an unsaturated ring.
• the ring to be formed is preferably, for example, a benzene ring or a naphthalene ring.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• R 3 is preferably an alkyl group or a heterocyclic group.
• the alkyl group represented by R 3 may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R 3 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by R 3 is preferably, for example, a methyl group, an ethyl group, or a t-butyl group.
• the aromatic ring group represented by R 3 may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by R 3 is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by R 3 is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group represented by R 3 may or may not have a substituent.
• the substituent is preferably an alkyl group, an alkylthio group, or an alkoxy group, for example.
• the heterocyclic group represented by R 3 is preferably a 5- or 6-membered ring.
• the heterocyclic group represented by R 3 is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by R 3 is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• the acyl group represented by R 3 is preferably an acyl group having 2 to 30 carbon atoms, more preferably an acyl group having 2 to 15 carbon atoms.
• the acyl group represented by R3 is preferably, for example, an acetyl group or a pivaloyl group.
• the carbamoyl group represented by R 3 may or may not have a substituent.
• the carbamoyl group represented by R 3 is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R 3 is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• Alkali metals include lithium, sodium, potassium and the like.
• organic bases include triethylamine, diisopropylethylamine, morpholine and the like.
• the compound represented by formula (1) is preferably a compound represented by formula (5) below, a tautomer thereof, or a salt thereof with an alkali metal or an organic base.
• Ar 1 and Ar 2 each independently represent a group represented by formula (A-1) below, a group represented by formula (A-2) below, or formula (A-3) below. represents a group represented by the following formula (A-4) or a group represented by the following formula (A-5), R is an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or represents a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• Ar 1 and Ar 2 each independently represent a group represented by formula (A-1) below, a group represented by formula (A-2) below, or formula (A-3) below. represents a group represented by the following formula (A-4) or a group represented by the following formula (A-5).
• Ar 1 and Ar 2 in formula (5) may be the same or different.
• Ar 1 and Ar 2 are each independently a group represented by the following formula (A-1), a group represented by the following formula (A-2), or the following formula (A-5 ) is preferably a group represented by
• Ar 1 is more preferably a group represented by formula (A-1) or a group represented by formula (A-5)
• Ar 2 is represented by formula (A- 2) is more preferred.
• R 1A represents a hydrogen atom, an alkyl group, a phenyl group, an acyl group or an alkoxycarbonyl group
• R 2A represents a hydrogen atom, a cyano group, a carbamoyl group or an alkylsulfonyl group
• R 3A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group
• R 4A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group.
• R 5A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• R 6A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• * represents a bonding position.
• R 1A represents a hydrogen atom, an alkyl group, a phenyl group, an acyl group or an alkoxycarbonyl group.
• R 1A is preferably a hydrogen atom or an alkyl group.
• the alkyl group represented by R 1A may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R 1A is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by R 1A is preferably, for example, a methyl group.
• the acyl group represented by R 1A is preferably an acyl group having 2 to 30 carbon atoms, more preferably an acyl group having 2 to 15 carbon atoms.
• the acyl group represented by R 1A is preferably, for example, an acetyl group or a pivaloyl group.
• the alkoxycarbonyl group represented by R 1A is preferably an alkoxycarbonyl group having 1 to 30 carbon atoms in the alkoxy moiety.
• the alkoxycarbonyl group represented by R 1A is preferably a methoxycarbonyl group or an ethoxycarbonyl group.
• R 2A represents a hydrogen atom, a cyano group, a carbamoyl group or an alkylsulfonyl group.
• R 2A is preferably a hydrogen atom.
• the carbamoyl group represented by R 2A may or may not have a substituent.
• the carbamoyl group represented by R 2A is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R 2A is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• the alkylsulfonyl group represented by R 2A is preferably an alkylsulfonyl group having 1 to 12 carbon atoms in the alkyl moiety.
• the alkylsulfonyl group represented by R 2A is preferably, for example, a methylsulfonyl group or an ethylsulfonyl group.
• R 3A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group.
• R 3A is preferably an alkyl group, an alkylthio group or an aromatic ring group, more preferably an alkyl group.
• the alkyl group represented by R 3A may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R 3A is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by R 3A is preferably, for example, a methyl group.
• the alkoxy group represented by R 3A may be a linear alkoxy group, a branched alkoxy group, or an alkoxy group having a cyclic structure.
• the alkoxy group represented by R 3A is preferably an alkoxy group having 1 to 30 carbon atoms.
• the alkoxy group represented by R 3A is preferably, for example, a methoxy group, an ethoxy group, an n-propoxy group, or an isopropoxy group.
• the alkylthio group represented by R 3A is preferably an alkylthio group having 1 to 12 carbon atoms in the alkyl moiety.
• the alkylthio group represented by R3A is preferably, for example, a methylthio group or an ethylthio group.
• the aromatic ring group represented by R 3A may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by R 3A is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by R 3A is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• R 4A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group.
• R 4A is preferably an alkyl group or an alkylthio group.
• the alkyl group represented by R4A may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R 4A is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• As the alkyl group represented by R4A for example, a methyl group is preferable.
• the alkoxy group represented by R4A may be a linear alkoxy group, a branched alkoxy group, or an alkoxy group having a cyclic structure.
• the alkoxy group represented by R 4A is preferably an alkoxy group having 1 to 30 carbon atoms.
• the alkoxy group represented by R 4A is preferably, for example, a methoxy group, an ethoxy group, an n-propoxy group or an isopropoxy group.
• the alkylthio group represented by R 4A is preferably an alkylthio group having 1 to 12 carbon atoms in the alkyl moiety.
• the alkylthio group represented by R4A is preferably, for example, a methylthio group or an ethylthio group.
• the aromatic ring group represented by R 4A may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by R 4A is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by R 4A is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• R 5A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• R5A is preferably a hydrogen atom or a sulfamoyl group.
• the carbamoyl group represented by R5A may or may not have a substituent.
• the carbamoyl group represented by R 5A is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R 5A is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• the sulfamoyl group represented by R5A may or may not have a substituent.
• the substituent is preferably an alkyl group, for example.
• the sulfamoyl group represented by R5A is preferably, for example, an unsubstituted sulfamoyl group, methylsulfamoyl group or dimethylsulfamoyl group.
• R 6A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• R6A is preferably a sulfamoyl group.
• the carbamoyl group represented by R6A may or may not have a substituent.
• the carbamoyl group represented by R 6A is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R 6A is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• the sulfamoyl group represented by R6A may or may not have a substituent.
• the substituent is preferably an alkyl group, for example.
• the sulfamoyl group represented by R6A is preferably, for example, an unsubstituted sulfamoyl group, methylsulfamoyl group or dimethylsulfamoyl group.
• R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• R is preferably an alkyl group or a heterocyclic group.
• the alkyl group represented by R may be a linear alkyl group, a branched alkyl group, or an alkyl group having a cyclic structure.
• the alkyl group represented by R is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.
• the alkyl group represented by R is preferably, for example, a methyl group, an ethyl group, an n-propyl group or a t-butyl group.
• the aromatic ring group represented by R may or may not have a substituent.
• the substituent is preferably a carbamoyl group or an acetyl group, for example.
• the aromatic ring group represented by R is preferably an aromatic ring group having 6 to 30 carbon atoms, more preferably an aromatic ring group having 6 to 20 carbon atoms.
• the aromatic ring group represented by R is preferably, for example, an aryl group (eg, phenyl group, p-tolyl group, naphthyl group, etc.).
• the heterocyclic group represented by R may or may not have a substituent.
• the substituent is preferably, for example, a methoxy group or a dimethylamino group.
• the heterocyclic group represented by R is preferably a 5- or 6-membered ring.
• the heterocyclic group represented by R is preferably a heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
• the number of heteroatoms in the heterocyclic group represented by R is preferably 1 to 3, more preferably 1 or 2, even more preferably 1.
• the acyl group represented by R is preferably an acyl group having 2 to 30 carbon atoms, more preferably an acyl group having 2 to 15 carbon atoms.
• the acyl group represented by R is preferably, for example, an acetyl group or a pivaloyl group.
• the carbamoyl group represented by R may or may not have a substituent.
• the carbamoyl group represented by R is preferably a carbamoyl group having 1 to 30 carbon atoms, more preferably a carbamoyl group having 1 to 15 carbon atoms.
• the carbamoyl group represented by R is preferably, for example, an N,N-dimethylcarbamoyl group, an N,N-diethylcarbamoyl group or a morpholinocarbonyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• Alkali metals include lithium, sodium, potassium and the like.
• organic bases include triethylamine, diisopropylethylamine, morpholine and the like.
• Ar 1 is a group represented by formula (A-1) or a group represented by formula (A-5), and Ar 2 is represented by formula (A -2), R is an alkyl group or a heterocyclic group, and X 1 - is a chloride ion or an acetate ion.
• the compound represented by formula (2) is preferably a compound represented by formula (4) below or a tautomer thereof.
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• X ⁇ represents chloride, bromide, iodide, acetate or phosphate.
• X 1 and X 2 in formula (4) have the same meanings as X 1 and X 2 in formula (3), and the preferred embodiments are also the same, so the description is omitted here.
• Y 1 , Y 2 , Y 3 and Y 4 in formula (4) have the same meanings as Y 1 , Y 2 , Y 3 and Y 4 in formula (3), and preferred embodiments are also the same. omitted.
• R 1 and R 2 in formula (4) have the same meanings as R 1 and R 2 in formula (3), and the preferred embodiments are also the same, so the description is omitted here.
• R 3 in formula (4) has the same meaning as R 3 in formula (3), and preferred embodiments are also the same, so description thereof is omitted here.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• X ⁇ is preferably chloride or acetate.
• the compound represented by formula (2) is preferably a compound represented by formula (6) below or a tautomer thereof.
• Ar 1 and Ar 2 are each independently a group represented by formula (A-1), a group represented by formula (A-2), and a group represented by formula (A-3). a group represented by formula (A-4) or a group represented by formula (A-5), and R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group .
• X ⁇ represents chloride, bromide, iodide, acetate or phosphate.
• Ar 1 and Ar 2 each independently represent a group represented by formula (A-1), a group represented by formula (A-2), and a group represented by formula (A-3). ), a group represented by formula (A-4) or a group represented by formula (A-5).
• a group represented by formula (A-1) represented by Ar 1 and Ar 2 , a group represented by formula (A-2), a group represented by formula (A-3) , the group represented by the formula (A-4) and the group represented by the formula (A-5) are represented by the formula (A-1) represented by Ar 1 and Ar 2 in the formula (5)
• a group represented by the formula (A-2), a group represented by the formula (A-3), a group represented by the formula (A-4) and represented by the formula (A-5) It is the same as the preferred embodiment of the group.
• Ar 1 and Ar 2 in formula (6) may be the same or different.
• Ar 1 is preferably a group represented by formula (A-1) or a group represented by formula (A-5).
• Ar 2 is preferably a group represented by formula (A-2).
• R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• R is preferably an alkyl group or a heterocyclic group.
• Specific examples of the alkyl group, aromatic ring group, heterocyclic group, acyl group and carbamoyl group represented by R in formula (6) are the alkyl group represented by R in formula (5), aromatic ring group, Specific examples of the heterocyclic group, acyl group and carbamoyl group are the same, and preferred embodiments are also the same.
• X ⁇ represents a chloride ion, bromide ion, iodide ion, acetate ion or phosphate ion.
• X ⁇ is preferably chloride or acetate.
• Ar 1 is a group represented by formula (A-1) or a group represented by formula (A-5), and Ar 2 is represented by formula (A -2), R is an alkyl group or a heterocyclic group, and X 1 - is a chloride ion or an acetate ion.
• the total content of the compound represented by formula (1) and the compound represented by formula (2) in the medium composition according to the present disclosure is 5 mg to 40 mg per 1000 mL of water contained in the medium composition. , more preferably 5 mg to 20 mg, even more preferably 10 mg to 20 mg.
• the compound represented by formula (1) preferably exhibits any one of orange, red, purple, or blue color.
• “orange” refers to a color with a hue angle (h) in the range of 45° to 70°.
• red refers to a color with a hue angle (h) in the range of 20° to 35°.
• “purple” refers to a color with a hue angle (h) in the range of 300° to 330°.
• blue refers to a color with a hue angle (h) in the range of 220° to 270°.
• the medium composition according to the present disclosure preferably further contains a pH indicator.
• the pH indicator is not particularly limited, and can be appropriately selected from known indicators and used. When selecting the pH indicator, for example, from the viewpoint of better discrimination from sugar-degrading bacteria, the color exhibited by the pH indicator under acidic conditions is different from the color exhibited by the compound represented by formula (1). preferably.
• pH indicators are described, for example, in paragraph [0028] of JP-A-2010-75179. These descriptions are incorporated herein by reference.
• Preferred pH indicators are phenol red, phenolphthalein, bromothymol blue (BTB), methyl yellow, methyl orange, methyl red, neutral red, malachite green, or congo red.
• the pH indicator preferably exhibits a color of either yellow, orange, red, purple or green under acidic conditions.
• the pH indicator is preferably selected according to the color exhibited by the compound represented by formula (1).
• the pH indicator exhibits a color with high contrast with the color exhibited by the compound represented by formula (1) under acidic conditions. preferable.
• yellow refers to a color with a hue angle (h) in the range of 85° to 95°.
• green refers to a color with a hue angle (h) in the range of 135° to 180°.
• Range refers to a color with a hue angle (h) in the range of 135° to 180°.
• Preferred combinations of the color that the pH indicator exhibits under acidic conditions and the color that the compound represented by Formula (1) exhibits are shown below.
• the color of the pH indicator under acidic conditions is yellow, and the color of the compound represented by formula (1) is red, purple or blue.
• the color of the pH indicator under acidic conditions is orange, and the color of the compound represented by formula (1) is red, purple or blue.
• the color of the pH indicator under acidic conditions is red, and the color of the compound represented by formula (1) is purple or blue.
• the color of the pH indicator under acidic conditions is purple, and the color of the compound represented by formula (1) is orange, red or blue.
• the color of the pH indicator under acidic conditions is green, and the color of the compound represented by formula (1) is orange, red, purple or blue.
• the medium composition according to the present disclosure preferably further contains a selection agent that suppresses the growth of bacteria other than enterohemorrhagic E. coli in the specimen.
• selective agents include bile salts, tellurite salts (eg, potassium tellurite), and the like.
• antibiotics are mentioned as said selection agent.
• Antibiotics include cephem antibiotics, penicillin antibiotics, and the like. Inclusion of at least one selection agent in the medium composition according to the present disclosure can suppress recent proliferation that may affect discrimination of enterohemorrhagic E. coli, including O157.
• penicillin antibiotics include benzylpenicillin, benzylpenicillin benzathine, pheneticillin, aspoxicillin, cyclacillin, renai-ipicillin, sulbenicillin, methicillin, oxacillin, penicillin N, penicillin O, penicillin V, penicillin G, cloxacillin, dicloxacillin, temocillin, piperacillin, azocillin, ampicillin, amoxicillin, bacampicillin, talampicillin, carbenicillin, ticarcillin, mezlocillin, avalacillin, sultamycillin, pibumecillinum and the like.
• cephem antibiotics include cefixime, cephalothin, cefazolin, ceftezole, cephaloridine, cephalexin, cefatridin propylene glycol, cefadroxil, cephradine, cefuroxazine, cefachlor, cefamandol, cefotiam, cefotiam hexetil, cefuroxime, and cefuroxime.
• the medium composition according to the present disclosure contains a selection agent, it may contain only one selection agent, or may contain two or more selection agents.
• the content of the selection agent is appropriately set according to the purpose.
• a medium composition according to the present disclosure can contain components contained in a medium commonly used for detecting enterohemorrhagic E. coli.
• Such ingredients include sugars, peptones, extracts, agar, and the like. The content of these components is appropriately set according to the purpose.
• sugars include D-sorbitol (D-sorbitol), inositol, adonitol, raffinose, rhamnose, salicin, sorbose and the like.
• D-sorbitol D-sorbitol
• inositol adonitol
• raffinose rhamnose
• salicin sorbose
• peptone include casein peptone, soybean peptone, and the like.
• extracts include yeast extract and the like.
• the medium can be made into a liquid medium, a semisolid medium, or a solid medium by adjusting the content of agar in the medium composition.
• a liquid medium is useful for a microdilution method using a microplate or the like.
• a semi-solid medium is suitable for puncture culture, and is useful as a medium for preservation of bacteria, transportation of specimens, and the like.
• a solid medium is useful as a medium for general bacterial culture and as a medium for plate dilution method.
• the method for detecting enterohemorrhagic Escherichia coli in a sample according to the present disclosure is a method for detecting enterohemorrhagic Escherichia coli in a sample in a medium containing the medium composition for detecting enterohemorrhagic Escherichia coli according to the present disclosure. and detecting the presence or absence of enterohemorrhagic E. coli.
• the specimen is cultured in a medium containing a medium composition for detecting enterohemorrhagic Escherichia coli, which enables good visualization of enterohemorrhagic Escherichia coli even when the use of a small amount of a dye compound is used.
• E. coli detection sensitivity is high.
• Preferred examples of the detection method according to the present disclosure include the following method.
• An oxidizing agent such as, for example, hydrogen peroxide solution is added to the composition for medium according to the present disclosure, which contains the compound represented by formula (1) and water.
• this oxidizing agent By the addition of this oxidizing agent, the compound represented by formula (1) in the medium composition changes to the compound represented by formula (2), which is its oxidant, and is represented by formula (1).
• the color exhibited by the compound disappears.
• the oxidizing agent is aqueous hydrogen peroxide
• the amount of the oxidizing agent to be added may be an amount equimolar to the amount of the compound represented by formula (1) contained in the medium composition according to the present disclosure. preferable.
• the medium composition according to the present disclosure containing the compound represented by formula (2) and water is preferably added with a pH indicator, and then added with additives such as the aforementioned selection agent, sugar, and extract. , stir.
• agar is added, heated and stirred, and then cooled to obtain a solid medium.
• a liquid or semi-liquid medium can be obtained.
• a sample is then inoculated into the resulting medium and cultured.
• Culture conditions include, for example, conditions for culturing at a temperature of 35° C. to 37° C. for 12 hours to 48 hours. In the above detection method, the reducing power of enterohemorrhagic E.
• the coli reduces the compound represented by formula (2), which is the oxidized form of the compound represented by formula (1), to be represented by formula (1). It changes to a compound, and colonies in which enterohemorrhagic E. coli are present become colored.
• sugar-degrading bacteria such as K. pneumoniae are present in the sample
• the sugar-decomposing bacteria decompose sugars, which lowers the pH of the culture medium. colored with an indicator.
• the use of a small amount of the compound represented by formula (1) makes it possible to easily distinguish between enterohemorrhagic Escherichia coli and sugar-degrading bacteria with the naked eye.
• Specimens in the detection method according to the present disclosure include foods suspected of food poisoning (e.g., lunch boxes, school lunches, sushi, etc.), water (e.g., rivers, lakes, wells, tap water, groundwater, etc.), feces (e.g., stool test specimen) and the like.
• foods suspected of food poisoning e.g., lunch boxes, school lunches, sushi, etc.
• water e.g., rivers, lakes, wells, tap water, groundwater, etc.
• feces e.g., stool test specimen
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• the compound represented by the formula (3) according to the present disclosure, its tautomer, or a salt thereof with an alkali metal or an organic base is represented by the formula (3 ), a tautomer thereof, or a salt thereof with an alkali metal or an organic base, and preferred embodiments are also the same, so description thereof is omitted here.
• the method for producing the compound represented by formula (3) according to the present disclosure is not particularly limited.
• the compound represented by formula (3) according to the present disclosure can be produced by known methods or with reference to known methods.
• the compound represented by formula (3) according to the present disclosure can be synthesized, for example, according to the method described in WO2018/051686. Specifically, the raw material aromatic hydrazine and aldehyde are condensed to obtain a hydrazone compound. Then, a separately prepared diazonium salt is added dropwise to the resulting hydrazone compound to synthesize it.
• the compound represented by Formula (3) according to the present disclosure can be suitably produced by the method described in Examples below.
• a compound or a tautomer thereof according to the present disclosure is a compound represented by Formula (4) or a tautomer thereof.
• the compound represented by formula (4) according to the present disclosure is an oxidant of the compound represented by formula (3) according to the present disclosure.
• X 1 and X 2 each independently represent -S-, -O- or -N(-Z 1 )-, and Z 1 is a hydrogen atom, an alkyl group, an aromatic ring group or represents a heterocyclic group.
• R3 represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group.
• X ⁇ represents chloride, bromide, iodide, acetate or phosphate.
• the compound represented by formula (4) according to the present disclosure or a tautomer thereof is the compound represented by formula (4) or a tautomer thereof described in the section of the medium composition according to the present disclosure. Since they have the same meaning and preferred embodiments are also the same, the description is omitted here.
• the method for producing the compound represented by formula (4) according to the present disclosure is not particularly limited.
• the compound represented by formula (4) according to the present disclosure can be produced by known methods or with reference to known methods.
• a compound represented by formula (4) according to the present disclosure can be produced using a compound represented by formula (3) according to the present disclosure. Specifically, it can be produced by oxidizing the compound represented by the formula (3) according to the present disclosure using an oxidizing agent such as hydrogen peroxide.
• Ar 1 and Ar 2 each independently represent a group represented by formula (A-1) below, a group represented by formula (A-2) below, or formula (A-3) below. represents a group represented by the following formula (A-4) or a group represented by the following formula (A-5), R is an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or represents a carbamoyl group.
• M represents a hydrogen atom, and the hydrogen atom may be dissociated to form a salt with an alkali metal or an organic base.
• R 1A represents a hydrogen atom, an alkyl group, a phenyl group, an acyl group or an alkoxycarbonyl group
• R 2A represents a hydrogen atom, a cyano group, a carbamoyl group or an alkylsulfonyl group
• R 3A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group
• R 4A represents an alkyl group, an alkoxy group, an alkylthio group or an aromatic ring group.
• R 5A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• R 6A represents a hydrogen atom, a cyano group, a carbamoyl group or a sulfamoyl group.
• * represents a bonding position.
• the compound represented by the formula (5) according to the present disclosure, its tautomer, or a salt thereof with an alkali metal or an organic base is represented by the formula (5 ), a tautomer thereof, or a salt thereof with an alkali metal or an organic base, and preferred embodiments are also the same, so description thereof is omitted here.
• a compound or a tautomer thereof according to the present disclosure is a compound represented by Formula (6) or a tautomer thereof.
• the compound represented by formula (6) according to the present disclosure is an oxidant of the compound represented by formula (5) according to the present disclosure.
• Ar 1 and Ar 2 are each independently a group represented by formula (A-1), a group represented by formula (A-2), and a group represented by formula (A-3). a group represented by formula (A-4) or a group represented by formula (A-5), and R represents an alkyl group, an aromatic ring group, a heterocyclic group, an acyl group or a carbamoyl group .
• X ⁇ represents chloride, bromide, iodide, acetate or phosphate.
• the group and the group represented by formula (A-5) are the group represented by formula (A-1) in formula (5), the group represented by formula (A-2), the group represented by formula (A-3 ), the group represented by formula (A-4) and the group represented by formula (A-5).
• the compound represented by formula (6) according to the present disclosure or a tautomer thereof is the compound represented by formula (6) or a tautomer thereof described in the section of the medium composition according to the present disclosure. Since they have the same meaning and preferred embodiments are also the same, the description is omitted here.
• the present disclosure discloses a first color-removable composition and a second color-removable composition.
• matters common to the first color-developing and erasing composition and the second color-developing and erasing composition will be described as "color-developing and erasing composition according to the present disclosure”.
• color-developing/decoloring property means the property of developing or decoloring due to a change in the maximum absorption wavelength due to oxidation-reduction.
• the first color-changing composition is a compound represented by formula (3), a tautomer thereof, a salt thereof with an alkali metal or an organic base, or a compound represented by formula (4) or Including its tautomers and water.
• compounds represented by formula (3), tautomers thereof, and salts of these with alkali metals or organic bases are also referred to as “compounds represented by formula (3), etc.”.
• the compound represented by Formula (4) or its tautomer is also called “the compound etc. which are represented by Formula (4).”
• the compound and the like represented by Formula (3) and the compound and the like represented by Formula (4) contained in the first color-developing/decoloring composition are compounds that develop or decolor by oxidation-reduction.
• the compound or the like represented by formula (4) is an oxidized form of the compound or the like represented by formula (3), and the compound or the like represented by formula (3) is oxidized to be represented by formula (4).
• the color exhibited by the compound or the like represented by formula (3) disappears.
• the compound or the like represented by the formula (4) is reduced to change into the compound or the like represented by the formula (3) to develop a color.
• the second decolorizing composition is a compound represented by formula (5), a tautomer thereof, a salt thereof with an alkali metal or an organic base, or a compound represented by formula (6) or Including its tautomers and water.
• compounds represented by formula (5), tautomers thereof, and salts of these with alkali metals and organic bases are also referred to as “compounds represented by formula (5), etc.”.
• the compound represented by formula (6) and its tautomer is also referred to as “the compound represented by formula (6) and the like”.
• the compound and the like represented by Formula (5) and the compound and the like represented by Formula (6) contained in the second color-developing/decoloring composition are compounds that develop or decolor by oxidation-reduction.
• the compound or the like represented by formula (6) is an oxidized form of the compound or the like represented by formula (5), and the compound or the like represented by formula (5) is oxidized to be represented by formula (6).
• the color exhibited by the compound or the like represented by Formula (5) disappears.
• the compound or the like represented by the formula (6) is reduced to change into the compound or the like represented by the formula (5) to develop a color.
• the first color-developing/decoloring composition may contain only one type of the first specific compound, or may contain two or more types.
• the content of the first specific compound in the first color-developing/erasing composition is determined, for example, by the type of substituent in the first specific compound.
• the content of the first specific compound in the first color-developing and decoloring composition is preferably 10% by mass to 50% by mass, and 10% by mass to It is more preferably 30% by mass, and even more preferably 10% to 20% by mass.
• the content of the first specific compound in the first color-developing and decoloring composition is 10% by mass or more with respect to the total mass of the color-developing and decoloring composition, the coloring density of the dye on the medium to be colored is increased. can be secured.
• the content of the first specific compound in the first color-removing composition is 50% by mass or less with respect to the total mass of the color-removing composition, a low-viscosity color-removing composition is obtained. Since it can be prepared, handling of the color-developing and decoloring composition becomes easy.
• the second color-developing/erasing composition may contain only one type of the second specific compound, or may contain two or more types.
• the content of the second specific compound in the second color-changing composition is determined, for example, by the type of the second specific compound, more specifically by the type of substituent in the second specific compound.
• the content of the second specific compound in the second color-developing and decoloring composition is preferably 10% by mass to 50% by mass, and 10% by mass to It is more preferably 30% by mass, and even more preferably 10% to 20% by mass.
• the coloring concentration of the dye on the medium to be colored is increased. can be secured.
• the content of the second specific compound in the second color-removing composition is 50% by mass or less with respect to the total mass of the color-removing composition, a low-viscosity color-removing composition is obtained. Since it can be prepared, handling of the color-developing and decoloring composition becomes easy.
• the decolorizing composition according to the present disclosure contains water.
• the color-changing composition according to the present disclosure can be produced by using water as a medium and dissolving a specific compound in the water.
• water is not particularly limited, for example, distilled water, ion-exchanged water, pure water, and the like are preferably used from the viewpoint of less impurities.
• the content of water in the color-developing and decoloring composition according to the present disclosure is preferably 50% to 90% by mass, more preferably 70% to 90% by mass, relative to the total mass of the color-developing and decoloring composition. and more preferably 80% by mass to 90% by mass.
• the color-developing and decoloring composition according to the present disclosure may contain an aqueous medium other than water.
• the color-developing and decoloring composition according to the present disclosure may contain a lipophilic medium, if necessary, within a range that does not impair the effects of the present disclosure.
• aqueous solvents other than water include organic solvents that are soluble in water (preferably soluble at 25°C).
• Such organic solvents include methanol, ethanol, isopropanol, n-propanol, butanol, n-pentanol, propylene glycol, ethylene glycol monoethyl ether, 1,2-hexanediol, butoxyethanol, phenoxyethanol, benzyl alcohol, propylene.
• the pH of the color-developing/decoloring composition according to the present disclosure is not particularly limited, and is appropriately set according to the purpose.
• the pH of the decolorizing composition according to the present disclosure is, for example, preferably 5 to 11, more preferably 6 to 11, and 7 to 10 from the viewpoint of the stability of the specific compound. is more preferred.
• the pH value in the present disclosure is the value at 25°C.
• the decolorizing composition according to the present disclosure may contain a pH adjuster.
• pH adjusters include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, ammonia, monoethanolamine, diethanolamine, guanidine and the like.
• the decolorizing composition according to the present disclosure can contain a surfactant.
• a surfactant When the color-developing/erasing composition according to the present disclosure contains a surfactant, it may contain only one type of surfactant, or may contain two or more types.
• Surfactants include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric or zwitterionic surfactants, and the like.
• anionic surfactants include monoalkylsulfuric acid or salts thereof, alkylbenzenesulfonic acids or salts thereof, ⁇ -olefin sulfonates or salts thereof, and particularly sodium dodecylbenzenesulfonate, sodium dodecylsulfate and sulfosuccinic acid half esters. (for example, monooctyl sulfosuccinate disodium salt), chain monoalkylethoxy sulfosuccinate alkali salts, and the like.
• nonionic surfactants include alkyl polyglycoside compounds, sorbitan ester compounds, acetylene glycol compounds, and the like.
• a quaternary ammonium compound is preferable, and a quaternary ammonium compound having a long-chain alkyl group is more preferable.
• the long-chain alkyl group includes, for example, an alkyl group having 10 or more carbon atoms, preferably an alkyl group having 10 to 24 carbon atoms.
• cationic surfactants include cetyltrimethylammonium chloride, dimethylstearylammonium chloride, trimethylacetylammonium bromide, stearyltrimethylammonium chloride, dimethylstearylbenzylammonium chloride, benzyltetradecyldimethylammonium chloride, dimethyldi-hydrogenated beef tallow.
• amphoteric or zwitterionic surfactants include betaine compounds such as fatty acid-amidoalkylbetaine and sulfobetaine.
• betaine compounds include lauryl hydroxysulfobetaine and the like.
• the decolorizing composition according to the present disclosure may contain a thickening agent.
• Thickeners include oleic acid, cetyl alcohol, oleyl alcohol, sodium chloride, cetearyl alcohol, stearyl alcohol and the like.
• the content of the thickener in the color-developing and decoloring composition according to the present disclosure is preferably 0.05% by mass to 20% by mass with respect to the total mass of the color-developing and decoloring composition, and 0.1 It is more preferably from 0.5% to 5% by mass, more preferably from 0.5% by mass to 10% by mass.
• the color-developing/decoloring composition according to the present disclosure may optionally contain coloring compounds other than the specific compounds (eg, pigments, dyes, etc.) as long as the effects of the present disclosure are not impaired.
• coloring compounds other than the specific compounds eg, pigments, dyes, etc.
• the color-developing and decoloring composition according to the present disclosure may contain a binder polymer, a polymerizable compound, a polymerization initiator, and the like.
• a binder polymer a polymerizable compound
• a polymerization initiator a polymerization initiator
• Known binder polymers, polymerizable compounds, and polymerization initiators can be used.
• the color-developing/decoloring composition according to the present disclosure can further contain other additives as necessary within a range that does not impair the effects of the present disclosure. Examples of additives for each application will be described later.
• the color-developing and erasable composition according to the present disclosure may be used as a color-developing and erasable composition for color toners.
• the content of the specific compound in the color-developing and decoloring composition for color toner is based on the total mass of the color-developing and decoloring composition for color toner. , preferably 0.1% by mass or more, more preferably 1% by mass to 20% by mass, and even more preferably 2% by mass to 10% by mass.
• the color-developing and decoloring composition for color toner preferably contains a binder resin. All commonly used binders can be used as the binder resin. Examples of binder resins include resins such as styrene resins, acrylic resins, styrene/acrylic resins, and polyester resins.
• the color-developing and decoloring composition for color toners contains, for example, inorganic particles and/or organic It can contain particles.
• the color-developing and decoloring composition for color toners preferably contains, for example, silica particles or titania particles (so-called titanium dioxide) whose surfaces are treated with an alkyl group-containing coupling agent or the like.
• the diameter is preferably between 10 nm and 500 nm.
• the content of these particles in the color-developing and decoloring composition for color toners is preferably 0.1% by mass to 20% by mass with respect to the total mass of the color-developing and decoloring composition for color toners.
• the color-developable and erasable composition for color toners preferably contains a release agent.
• the mold release agent all conventionally used mold release agents can be used. Specific examples of release agents include polyolefins such as low-molecular-weight polypropylene, low-molecular-weight polyethylene, and ethylene-propylene copolymers, microcrystalline wax, carnauba wax, sasol wax, and paraffin wax.
• the content of the releasing agent in the color forming and decoloring composition for color toners is preferably 1% by mass to 5% by mass with respect to the total mass of the color forming and decoloring composition for color toners.
• the color-developable and erasable composition for color toners preferably contains a charge control agent.
• Charge control agents include quaternary ammonium salt compounds, calixarene compounds and the like.
• the color-developing and decoloring composition for color toner can contain a carrier.
• the carrier may be an uncoated carrier composed only of magnetic material particles such as iron or ferrite, or a resin-coated carrier in which the surfaces of magnetic material particles are coated with a resin or the like.
• the volume average particle size of the carrier is preferably 30 ⁇ m to 150 ⁇ m.
• the volume-average particle size of the carrier is a value measured using a particle size distribution analyzer employing a dynamic light scattering method.
• the decolorizing composition according to the present disclosure may be used as an ink for inkjet recording.
• the ink for inkjet recording uses, for example, an aqueous medium containing water as a medium, and at least one specific compound in the aqueous solvent. It is preferably an ink obtained by dissolving seeds.
• the content of the specific compound in the inkjet recording ink is 0.2% by mass to 10% by mass with respect to the total mass of the inkjet recording ink. % by mass is preferable, and 1 to 6% by mass is more preferable.
• the inkjet recording ink may contain other dyes.
• the total content of the dyes is preferably within the above range.
• the aqueous medium containing water contains water as a main component.
• Constaining water as a main component means that the proportion of water in the aqueous medium is 50% by mass or more, preferably 60% by mass or more, and more preferably 70% by mass or more. , more preferably 80% by mass or more.
• the proportion of water in the aqueous medium may be 100% by mass.
• water is not particularly limited, for example, distilled water, ion-exchanged water, pure water, and the like are preferably used from the viewpoint of less impurities.
• Examples of the medium other than water contained in the aqueous medium include water-miscible organic solvents.
• Water-miscible organic solvents include monohydric alcohols (e.g., methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, t-butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol, etc.), polyhydric alcohols Alcohol (e.g.
• glycol derivatives e.g., ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, etc.
• glycol derivatives e.g.
• ethanolamine diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyl diethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenetriamine, triethylenetetramine, polyethyleneimine, tetramethylpropylenediamine, etc.
• other polar solvents e.g.
• the inkjet recording ink may optionally contain a drying inhibitor (also referred to as a "wetting agent"), an antifading agent, and an emulsification stabilizer.
• a drying inhibitor also referred to as a "wetting agent”
• an antifading agent also referred to as a "wetting agent”
• an emulsification stabilizer agents, penetration accelerators, ultraviolet absorbers, preservatives, antifungal agents, pH adjusters, surface tension adjusters, antifoaming agents, viscosity adjusters, dispersants, dispersion stabilizers, rust inhibitors, chelating agents, etc. may contain additives.
• the anti-drying agent is used for the purpose of preventing clogging due to drying of the ink for ink jet recording at the ink ejection port of the nozzle used in the ink jet recording system.
• a water-soluble organic solvent having a vapor pressure lower than that of water is preferred.
• Specific examples of anti-drying agents include ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol, 2-methyl-1,3-propanediol, 1,2,6-hexanetriol, and acetylene glycol.
• Polyhydric alcohol compounds represented by derivatives, glycerin, trimethylolpropane, etc.; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl ether, etc.
• heterocyclic compounds such as 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-ethylmorpholine; sulfolane, dimethyl sulfoxide, 3 - sulfur-containing compounds such as sulfolene; polyfunctional compounds such as diacetone alcohol and diethanolamine; urea derivatives; Among these, polyhydric alcohol compounds such as glycerin and diethylene glycol are preferable as drying inhibitors.
• the ink for inkjet recording contains an anti-drying agent, it may contain only one kind of anti-drying agent, or may contain two or more kinds of anti-drying agents.
• the content of the anti-drying agent is preferably 10% by mass to 50% by mass with respect to the total mass of the ink for inkjet recording.
• Ultraviolet absorbers are used for the purpose of improving the storage stability of images.
• the ultraviolet absorber is described in JP-A-58-185677, JP-A-61-190537, JP-A-2-782, JP-A-5-197075, JP-A-9-34057, etc.
• inkjet recording ink contains an ultraviolet absorber, it may contain only one ultraviolet absorber, or may contain two or more ultraviolet absorbers.
• the content of the ultraviolet absorber is appropriately set according to the purpose.
• Antifading agents are used for the purpose of improving the storage stability of images.
• various organic anti-fading agents and metal complex anti-fading agents can be used.
• organic anti-fading agents include hydroquinone compounds, alkoxyphenol compounds, dialkoxyphenol compounds, phenol compounds, aniline compounds, amine compounds, indane compounds, chroman compounds, alkoxyaniline compounds, and heterocyclic compounds.
• metal complex-based anti-fading agents include nickel complexes and zinc complexes. Specific examples of metal complex-based antifading agents include Research Disclosure No. 17643, Sections VII I-J, Research Disclosure No. 15162, Research Disclosure No. 18716, page 650, left column, Research Disclosure No. 36544, page 527, Research Disclosure No.
• the ink for inkjet recording contains an antifading agent, it may contain only one type of antifading agent, or may contain two or more types.
• the content of the antifading agent is appropriately set according to the purpose.
• Antifungal agents include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, ethyl p-hydroxybenzoate, 1,2-benzisothiazolin-3-one and salts thereof.
• the ink for inkjet recording may contain only one antifungal agent, or may contain two or more antifungal agents.
• the content of the antifungal agent is preferably 0.02% by mass to 1% by mass with respect to the total mass of the ink for inkjet recording.
• a pH adjuster is used, for example, for the purpose of improving the storage stability of an ink for inkjet recording.
• pH adjusters include neutralizing agents (eg, organic bases, inorganic alkalis, etc.).
• the pH adjuster is preferably added so that the ink for inkjet recording has a pH of 6-10, more preferably 7-9.
• Surface tension modifiers include nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants, and the like.
• the surface tension of the ink for inkjet recording is preferably 25 mN/m to 70 mN/m, more preferably 25 mN/m to 60 mN/m at 25°C.
• the viscosity of the ink for inkjet recording is preferably 30 mPa ⁇ s or less, more preferably 20 mPa ⁇ s or less at 25°C.
• Surface tension modifiers include fatty acid salts, alkyl sulfate salts, alkylbenzene sulfonates, alkyl naphthalene sulfonates, dialkyl sulfosuccinates, alkyl phosphate salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl sulfates.
• Anionic surfactants such as salts; polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester, oxy Surfactants such as nonionic surfactants such as ethyleneoxypropylene block copolymers; are preferred.
• SURFYNOLS manufactured by Air Products & Chemicals
• acetylenic polyoxyethylene oxide surfactant can also be suitably used as a surface tension modifier.
• an amine oxide type amphoteric surfactant such as N,N-dimethyl-N-alkylamine oxide can also be suitably used as a surface tension modifier.
• Japanese Patent Application Laid-Open No. 59-157636, pages (37) to (38), Research Disclosure No. 308119 (1989) can also be used as surface tension modifiers.
• the ink for inkjet recording contains a surface tension modifier, it may contain only one surface tension modifier, or may contain two or more thereof.
• the content of the surface tension modifier is appropriately set according to the purpose.
• antifoaming agents examples include fluorine-based compounds and silicone-based compounds.
• Chelating agents such as ethylenediaminetetraacetic acid (EDTA) can also be used as antifoaming agents.
• EDTA ethylenediaminetetraacetic acid
• the ink for inkjet recording contains an antifoaming agent, it may contain only one antifoaming agent, or may contain two or more antifoaming agents.
• the content of the antifoaming agent is appropriately set according to the purpose.
• the present disclosure discloses a first dyeing and a second dyeing.
• matters common to the first dyed article and the second dyed article will be described as "the dyed article according to the present disclosure”.
• the first dyeing contains the compound represented by the formula (3), its tautomer, or its salt with an alkali metal or an organic base.
• the second dyeing contains the compounds represented by formula (5), their tautomers or their salts with alkali metals or organic bases.
• the compound represented by the formula (3), its tautomer, or its salt with an alkali metal or an organic base may be collectively referred to as "the first specific compound B”.
• the compound represented by the formula (5), its tautomer, or its salt with an alkali metal or an organic base may be collectively referred to as "the second specific compound B”.
• the first specific compound B and the second specific compound B may be collectively referred to as "the specific compound B".
• the first dyed article may contain a dye compound (eg, pigment, dye, etc.) other than the first specific compound B, if necessary, as long as the effects of the present disclosure are not impaired.
• the dyed portion containing the first specific compound B in the first dyed article may be part of the dyed article or may be the entire dyed article.
• the second dyed article may contain a dye compound (eg, pigment, dye, etc.) other than the second specific compound B, if necessary, as long as the effects of the present disclosure are not impaired.
• the dyed portion containing the second specific compound B in the second dyed article may be part of the dyed article or may be the entire dyed article.
• Materials to be dyed in the dyed material according to the present disclosure include natural fibers such as silk, cotton, and hemp; synthetic fibers such as nylon, polyester, acrylic, and polyurethane; inorganic materials such as glass, metal, and ceramics; plain paper, and resin-coated paper. , paper such as inkjet recording paper;
• the dyed article according to the present disclosure is produced by a dyeing method using the specific compound B, more specifically, a dyeing method using the color-developing and decoloring composition according to the present disclosure containing at least one specific compound B. be able to.
• the dyeing method using the specific compound B may be a method using the specific compound B as a dye.
• a dyeing method for obtaining a dyed article according to the present disclosure a known dyeing method can be used except that the specific compound B is used.
• methods such as immersion, kneading, coating, printing, and inkjet printing can be employed.
• the diazonium salt solution was added dropwise thereto while maintaining the internal temperature at 10° C. or lower. After dropping, the mixture was stirred for 1 hour while keeping the internal temperature at 10°C or lower. After that, the mixture was allowed to cool to room temperature (25° C.) and further stirred for 1 hour. 100 mL of ion-exchanged water was added thereto, and the precipitated solid (so-called crude substance) was collected by filtration. The resulting crude product was dissolved in 30 mL of a 3 mol/L sodium hydroxide aqueous solution in a 100 mL three-necked flask and stirred at 50° C. for 1 hour.
• the molecular weight of compound D-1 was 278.3. Compound D-1 was confirmed to have the following structure by 1 H-NMR.
• the molecular weight of compound D-2 was 327.4. Compound D-2 was confirmed to have the following structure by 1 H-NMR.
• the molecular weight of compound D-3 was 410.5.
• Compound D-3 was confirmed to have the following structure by 1 H-NMR.
• the molecular weight of compound D-4 was 459.5.
• Compound D-4 was confirmed to have the following structure by 1 H-NMR.
• the diazonium salt solution was added dropwise thereto while maintaining the internal temperature at 10° C. or lower. If the pH of the reaction solution becomes 7 or less during the dropwise addition, dropwise addition of the diazonium salt solution is interrupted, and a solution obtained by dissolving 5 mL of triethylamine in 30 mL of methanol (hereinafter also referred to as "triethylamine solution") is added to the inside of the reaction solution. It was added dropwise while maintaining the temperature below 10°C. Then, when the dropwise addition of the triethylamine solution was completed, the dropwise addition of the diazonium salt solution was resumed.
• triethylamine solution a solution obtained by dissolving 5 mL of triethylamine in 30 mL of methanol
• the molecular weight of compound D-5 was 296.4.
• Compound D-5 was confirmed to have the following structure by 1 H-NMR.
• the diazonium salt solution was added dropwise thereto while maintaining the internal temperature at 10° C. or less. After dropping, the mixture was stirred for 1 hour while keeping the internal temperature at 10°C or lower. After that, the mixture was allowed to cool to room temperature (25° C.) and further stirred for 1 hour. 100 mL of ion-exchanged water was added thereto, and the precipitated solid (so-called crude substance) was collected by filtration. The obtained solid was purified by silica gel column chromatography to obtain 3.1 g of compound D-6 (yield: 69%).
• the molecular weight of compound D-6 was 246.2.
• Compound D-6 was confirmed to have the following structure by 1 H-NMR.
• Comparative Example 1 Comparative compound 1 having the following structure was used.
• the molecular weight of Comparative Compound 1 is 350.4.
• enterohemorrhagic E. coli type: O157
• K. pneumoniae are cultured (culturing temperature: 37°C, culture time: 20 hours) using the enterohemorrhagic E. coli detection medium obtained above, The medium after culturing was visually observed. Then, the visibility of enterohemorrhagic E. coli (O157) was evaluated based on whether it was possible to clearly distinguish between enterohemorrhagic E. coli (O157) and K. pneumoniae with the naked eye. Table 2 shows the results.
• the enterohemorrhagic Escherichia coli detection medium composition of the example allows enterohemorrhagic Escherichia coli (O157) to be well visualized even when the amount of dye compound used is small, and Klebsiella pneumoniae (K. pneumoniae) could be clearly distinguished.

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