JP5112660B2 - New antibacterial agent - Google Patents

Description

  The present invention relates to an antibacterial agent having low mutagenicity. More specifically, the present invention relates to an antibacterial agent having low mutagenicity containing a sulfonium salt.

  Since the growth of bacteria may cause deterioration of industrial materials and final products, decrease in productivity, and decrease in product quality, many antibacterial agents are currently used for industrial use. Examples of industrial general-purpose antibacterial agents include carbendazine used for plastics, orthophenylphenol used for leather, and glutaraldehyde used for environmental hygiene purposes.

  However, when these antibacterial agents are continuously used, the antibacterial effect often decreases due to microorganisms acquiring resistance to the antibacterial agent. Measures have been taken to avoid resistance and maintain the antibacterial effect by replacing the antibacterial agent used every certain period, but this measure also has a limit, especially when bacterial contamination is severe. Since antibacterial properties of existing antibacterial agents are thought to decrease with resistance, antibacterial agents that are effective against bacteria that have become resistant to existing antibacterial agents, including compounds with novel chemical structures, are always available. It has been demanded.

  In addition, industrial antibacterial agents tend to place more emphasis on their antibacterial effects than safety to the human body and the environment, and there are few antibacterial agents containing highly toxic compounds among widely used antibacterial agents. Absent. In particular, general antibacterial agents include compounds that have the property of causing changes in genetic information that may cause tumors and genetic diseases in the human body and change ecosystems in environmental organisms, that is, mutagenicity. ing. Therefore, as antibacterial agents to be developed in the future, antibacterial agents with low mutagenicity are desired in order to ensure safety to living bodies and the environment.

A sulfonium compound having a sulfonium ion in the molecule is known as one of the compounds having an antibacterial effect. The sulfonium compound is classified as a cationic antibacterial agent in terms of chemical structure, like the quaternary ammonium compound widely used as an antibacterial agent.
Regarding the antibacterial effect relating to the sulfonium compound, for example, in Japanese Patent Application Laid-Open No. 2000-16908 (Patent Document 1), an antibacterial resin formed from an antibacterial polymer having a sulfonium base in the main chain and / or side chain has an antibacterial effect. It is described that there is. Regarding antibacterial properties of sulfonium compounds, for example, Reddy et al. Have reported that 1-aroyl-4-oxo-4-allyl-2-butenylide dimethylsulfoniums have antibacterial properties (non-patented). Literature 1: Biochemistry International, 19 (2), 215-218, 1989), and Freedlander, BL et al. Reported that dimethylsulfonium nitrate is weak but antibacterial (Non-patent Literature 2: Proceedings of the Society for Experimental Biology and Medicine, 63, 319-322, 1946). However, reported examples of sulfonium salts having a limited structure presented in the present invention and having sulfonium ions in the limited ClogP range have a high antibacterial effect and low mutagenicity. Never before.
Japanese Unexamined Patent Publication No. 2000-16908 Biochemistry International, 19 (2), 215-218, 1989 Proceedings of the Society for Experimental Biology and Medicine, 63, 319-322, 1946

  An object of the present invention is to provide an antibacterial agent having high antibacterial effect and low mutagenicity, and more specifically, an antibacterial agent comprising a sulfonium salt having high antibacterial effect and low mutagenicity. It is an object to provide an agent.

The inventors of the present invention have made diligent efforts to solve the above-mentioned problems, and a sulfonium salt having a specific structure among various sulfonium salts and having a cation in the limited ClogP range has sufficient antibacterial effect. And having low mutagenicity, the present invention was completed based on this finding.

｛式中、Ｗ₃はイオウ原子に結合する３個のＷを示し、３個のＷは互いに同一又は異なっていてもよく、それぞれ独立に炭素数1〜20のアルキル基〔該アルキル基は、水酸基、ハロゲン原子、−N(R¹)(R²)、−COR³、−SO₃M¹、−R⁴-N(R⁵)(R⁶)、−R⁷-COR⁸、−R⁹-SO₃M²、−COAr（R¹、R²、R⁵、及びR⁶は、互いに同一又は異なっていてもよく、それぞれ独立に水素原子又は炭素数1〜20のアルキル基を示し；R³及びR⁸は、互いに同一又は異なっていてもよく、それぞれ独立に水素原子、−OM³、炭素数1〜20のアルキル基、炭素数1〜20のアルコキシ基、又はアミノ基を示し；R⁴、R⁷、及びR⁹は、互いに同一又は異なっていてもよく、それぞれ各々独立に炭素数1〜20のアルキレン基を示し；M¹、M²、及びM³は、互いに同一又は異なっていてもよく、それぞれ独立に一価のカチオンを形成するのに必要な原子又は分子を示し；Arは芳香族化合物（該芳香族化合物は置換基を有していてもよく、環構成原子としてヘテロ原子を１又は２個以上含んでいてもよい）の残基を示す）、及び-(OCH₂CH₂)_j-CH₃（jは1〜10の整数）からなる群から選ばれる置換基を１個又は２個以上有していてもよい〕、炭素数1〜20のアルコキシ基（該アルコキシ基は、水酸基、ハロゲン原子、−N(R¹)(R²)、−COR³、−SO₃M¹、−R⁴-N(R⁵)(R⁶)、−R⁷-COR⁸、又は−R⁹-SO₃M²、−COAr、及び-(OCH₂CH₂)_j-CH₃からなる群から選ばれる置換基を１個又は２個以上有していてもよい）、又は−COArを示す}を有し、かつ、該スルホニウム塩のカチオンのClogPが7以上18未満である抗菌剤が提供される。 That is, according to the present invention, an antibacterial agent containing a sulfonium salt as an active ingredient, wherein the cation of the sulfonium salt has the following structure:

{Wherein W ₃ represents _three Ws bonded to a sulfur atom, and the three Ws may be the same or different from each other, and each independently represents an alkyl group having 1 to 20 carbon atoms [the alkyl group is Hydroxyl group, halogen atom, -N (R ¹ ) (R ² ), -COR ³ , -SO ₃ M ¹ , -R ⁴ -N (R ⁵ ) (R ⁶ ), -R ⁷ -COR ⁸ , -R ⁹ —SO ₃ M ² , —COAr (R ¹ , R ² , R ⁵ , and R ⁶ may be the same or different from each other and each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; R ³ and R ⁸ may be the same or different from each other, and each independently represents a hydrogen atom, —OM ³ , an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an amino group; R ⁴ , R ⁷ and R ⁹ may be the same or different from each other, and each independently represents an alkylene group having 1 to 20 carbon atoms; M ¹ , M ² and M ³ are the same or different from each other; You can, Each independently represents an atom or molecule necessary to form a monovalent cation; Ar represents an aromatic compound (the aromatic compound may have a substituent, and a hetero atom as a ring member atom); One or more substituents selected from the group consisting of — (OCH ₂ CH ₂ ) _j —CH ₃ (j is an integer of 1 to 10). Or an alkoxy group having 1 to 20 carbon atoms (the alkoxy group is a hydroxyl group, a halogen atom, -N (R ¹ ) (R ² ), -COR ³ , -SO ₃ M ¹ , -R ⁴ -N (R ⁵ ) (R ⁶ ), -R ⁷ -COR ⁸ , or -R ⁹ -SO ₃ M ² , -COAr, and-(OCH ₂ CH ₂ ) _j -CH ₃ 1 or 2 or more substituents selected from the group), or —COAr}, and the ClogP of the cation of the sulfonium salt is 7 or more and less than 18 Provided.

  According to a preferred embodiment of the above invention, an antibacterial agent having ClogP of 9 or more and less than 16, and more preferably ClogP of 11 or more and less than 14 is provided. According to a further preferred embodiment, any one of the above antibacterial agents which is an industrial antibacterial agent is provided. Further, an antibacterial composition containing the above antibacterial agent and one or more additives is also provided by the present invention, and an industrial antibacterial composition is provided as a preferred embodiment. Examples of the additive include a surfactant, a binder, and a stabilizer.

  Another aspect of the present invention is the use of a sulfonium salt having a cation represented by the above formula (I) for the production of the antibacterial agent or the antibacterial composition, and a method for inhibiting the growth of microorganisms. There is provided a method comprising a step of contacting and / or adding a sulfonium salt having a cation represented by the above formula (I) to an industrial product or an industrial raw material.

According to the present invention, an antibacterial agent comprising a sulfonium salt having a high antibacterial effect and low mutagenicity is provided.

  In the present specification, a compound having a sulfonium salt or a sulfonium ion means a sulfonium compound comprising a sulfonium ion having a positive charge on a trivalent sulfur atom and an anion.

  In the present specification, the aromatic compound means a cyclic conjugated compound having 4n + 2 π electrons in the ring, and may be either a monocyclic aromatic compound or a condensed polycyclic aromatic compound. Good. For example, benzene, 1,3,5,7,9-decapentaene, 1,3,5,7,9,11,13-tetradecapentaene, naphthalene, anthracene, phenanthrene, indene, tetralin, azulene, perinaphthyl, etc. Preferably, benzene or naphthalene is mentioned, More preferably, benzene is mentioned. The aromatic compound may contain one or more hetero atoms as ring constituent atoms. A hetero atom is a non-metal or metal atom other than a carbon atom, preferably a non-metal atom, and examples thereof include a nitrogen atom, an oxygen atom, and a sulfur atom. When two or more heteroatoms are contained, these heteroatoms may be the same or different. Examples of the aromatic compound containing a hetero atom as a ring atom include pyridine, pyrrole, indolizine, thiophene, furan, cyclopentadienyl ion, tropone, tropolone, ferrocene, borazole, silicon benzene, and the like. The residue represented by Ar means the remaining monovalent group obtained by removing one hydrogen atom from an aromatic compound, and a residue obtained by removing a hydrogen atom at any position can be used. . Ar is preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and particularly preferably a phenyl group.

  In this specification, the alkyl group may be linear, branched, cyclic, or a combination thereof (unless otherwise specified, in this specification, a functional group containing an alkyl group and an alkyl moiety). The alkyl part of (for example, the alkyl part of the alkoxy group) has the same meaning). Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1 , 1-dimethylpropyl group, n-hexyl group, isohexyl group, linear or branched heptyl group, octyl group, nonyl group, decyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, or cyclohexyl group, etc. Can be mentioned.

In the present specification, the term “halogen atom” may be any of a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
Examples of the alkylene group having 1 to 20 carbon atoms include divalent groups formed by removing any two hydrogen atoms of a straight chain, branched chain, cyclic, or combination thereof having 1 to 20 carbon atoms. Can be mentioned.
Examples of the atom or molecule necessary for forming a monovalent cation represented by M ¹ , M ² , or M ³ include a hydrogen atom and an alkali metal atom (such as lithium, sodium, and potassium).

In the present specification, when a functional group such as an alkyl group may have one or more specific substituents, the substitution position or number of the substituents is not particularly limited, and 2 When it has more than one substituent, these substituents may be the same or different.
When the aromatic ring represented by Ar has a substituent, the type of substituent is not particularly limited. Examples of the substituent include a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a phenyl group. It is done. The number of substituents and the substitution position are not particularly limited, but when the residue of the aromatic compound represented by Ar is a phenyl group, it is preferable that one substituent is present in the para position. Ar is preferably a residue of an unsubstituted aromatic compound, more preferably an unsubstituted phenyl group.

  The three Ws may be the same or different, but the two Ws are preferably the same. W is preferably an unsubstituted alkyl group having 4 to 12 carbon atoms, an unsubstituted alkoxy group having 4 to 14 carbon atoms, or an alkyl group having 4 to 14 carbon atoms having -COAr as a substituent. An alkyl group having 4 to 12 carbon atoms or a methyl group having —COAr as a substituent is more preferable.

In this specification, “ClogP” means logP (log [water / octanol partition coefficient]) predicted by calculation from the chemical structure. Many methods have been developed to predict logP from chemical structure by calculation. Typical examples include ClogP (automatic calculation software example 1: clogptalk 4.82 (trademark) (2006), Daylight CIS Inc.), Kow WIN (automatic calculation software example) 2: KowWIN Version 1.66 (2000), Syracuse Res. Corp.) and Pallas (automatic calculation software example 3: Pallas prolog PVersion 6.0 (1995), CompuDrug Chemistry Ltd.). Of these, clogptalk 4.82 (trademark) is preferably used. Hereinafter, the ClogP values referred to in this specification are calculated using clogptalk 4.82 (trademark) .

  Specific examples of the cation of the sulfonium salt used in the present invention include the following ions.

In the sulfonium salt used in the present invention, the anion serving as a counter ion for the cation of the sulfonium salt is not particularly limited, and for example, a monovalent to tetravalent inorganic or organic anion may be used. Examples of the anion include the following examples.
・ Examples of inorganic anions
^{F -, Cl -, Br -} , I -, ClO 4 -, IO 3 -, IO 4 -, MnO 4 -, NO 3 -, NCS -, BrO 3 -, HCO 3 -, ReO 4 -, BrO 4 - ^{_{, C (CN) 3 -,}} CN, ClO 2 -, ClO 3 -, [Co (NO 2) 4 (NH 3) 2] -, H 2 AsO 4 -, HCO 3 -, H 2 PO 4 -, HS _{^{-, HSO 3 -, SCSN 3}} -, HCOO -, OH -, BF 4 -, PF 6 -
CrO ₄ ^2- , SO ₄ ^2- , SiF ₆ ^2- , CO ₃ ^2- , Cr ₂ O ₇ ^2- , B ₄ O ₇ ^2- , MnO ₄ ^2- , S ^2- , SO ₃ ^2- , S ₂ O ₃ ^2- , WO ₄ ^2- , CO ₃ ^2- , C ₂ O ₄ ^2- , CrO ₄ ^2- ,
[Fe (CN) ₅ NO] ^2- , O ^2- , HPO ₄ ^2- , S ₂ O ₄ ^2- , S ₂ O ₆ ^2- , S ₂ O ₈ ^2- , SeO ₄ ^2-
PO ₄ ^3- , [Fe (CN) ₆ ] ^3- , [Co (CN) ₆ ] ^3- , [Fe (CN) ₆ ] ^4-

・ Examples of organic anions
^{_{CH 3 COO -, CH 3 CH}} 2 COO -, CH 3 (CH 2) 2 COO -, CH 3 (CH 2) 3 COO -, CH 3 (CH 2) 4 COO -, CH 3 (CH 2) 5 COO ^{_{-, CH 3 (CH 2)}} 6 COO -, CH 3 (CH 2) 7 COO -, CH 3 (CH 2) 8 COO -, CH 3 (CH 2) 9 COO -, CH 3 (CH 2) 10 COO ^{_{-, FCH 2 COO -, F}} (CH 2) 10 COO -, ClCH 2 COO -, Cl (CH 2) 10 COO -, BrCH 2 COO -, Br (CH 2) 10 COO -, ICH 2 COO -, I (CH _{2) 10} COO ^{-,
_{CH 3 SO 3 -, CH 3}} CH 2 SO 3 -, CH 3 (CH 2) 2 SO 3 -, CH 3 (CH 2) 3 SO 3 -, CH 3 (CH 2) 4 SO 3 -, CH 3 ( ^{_{CH 2) 5 SO 3 -,}} CH 3 (CH 2) 6 SO 3 -, CH 3 (CH 2) 7 SO 3 -, CH 3 (CH 2) 8 SO 3 -, CH 3 (CH 2) 9 SO 3 ^{_{-, CH 3 (CH 2)}} 10 SO 3 -, FCH 2 SO 3 -, F (CH 2) 10 SO 3 -, ClCH 2 SO 3 -, Cl (CH 2) 10 SO 3 -, BrCH 2 SO 3 - _{, Br (CH 2) 10 SO} 3 -, ICH 2 SO 3 -, I (CH 2) 10 SO 3 -,
^{_{CF 3 COO -, CF 3 CF}} 2 COO -, CF 3 (CF 2) 2 COO -, CF 3 (CF 2) 3 COO -, CF 3 (CF 2) 4 COO -, CF 3 (CF 2) 5 COO ^- ,
_{CF 3 (CF 2) 6 COO} -, CF 3 (CF 2) 7 COO -, CF 3 (CF 2) 8 COO -, CF 3 (CF 2) 9 COO -, CF 3 (CF 2) 10 COO -, ^{_{FCF 2 COO -, F (CF}} 2) 10 COO -, ClCF 2 COO -, Cl (CF 2) 10 COO -, BrCF 2 COO -, Br (CF 2) 10 COO -, ICF 2 COO -, I (CF _{2) 10} COO ^{-,
_{CF 3 SO 3 -, CF 3}} CF 2 SO 3 -, CF 3 (CF 2) 2 SO 3 -, CF 3 (CF 2) 3 SO 3 -, CF 3 (CF 2) 4 SO 3 -, CF 3 ( ^{_{CF 2) 5 SO 3 -,}} CF 3 (CF 2) 6 SO 3 -, CF 3 (CF 2) 7 SO 3 -, CF 3 (CF 2) 8 SO 3 -, CF 3 (CF 2) 9 SO 3 ^{_{-, CF 3 (CF 2)}} 10 SO 3 -, FCF 2 SO 3 -, F (CF 2) 10 SO 3 -, ClCF 2 SO 3 -, Cl (CF 2) 10 SO 3 -, BrCF 2 SO 3 - _{, Br (CF 2) 10 SO} 3 -, ICF 2 SO 3 -, I (CF 2) 10 SO 3 -,
^{_{CH 3 OCOO -, CH 3 OCH}} 2 COO -, CH 3 O (CH 2) 2 COO -, CH 3 O (CH 2) 3 COO -, CH 3 O (CH 2) 4 COO -, CH 3 O (CH ^{_{2) 5 COO -, CH 3}} O (CH 2) 6 COO -, CH 3 O (CH 2) 7 COO -, CH 3 O (CH 2) 8 COO -, CH 3 O (CH 2) 9 COO -, _{CH 3 O (CH 2) 10} COO -,
^{_{CH 3 OSO 3 -, CH 3}} OCH 2 SO 3 -, CH 3 O (CH 2) 2 SO 3 -, CH 3 O (CH 2) 3 SO 3 -, CH 3 O (CH 2) 4 SO 3 -, _{CH 3 O (CH 2) 5} SO 3 -, CH 3 O (CH 2) 6 SO 3 -, CH 3 O (CH 2) 7 SO 3 -, CH 3 O (CH 2) 8 SO 3 -, CH 3 _{O (CH 2) 9 SO 3} -, CH 3 O (CH 2) 10 SO 3 -,
^{_{CH 3 OCH 2 OCOO -, CH}} 3 O (CH 2 O) 2 COO -, CH 3 O (CH 2 O) 3 COO -, CH 3 O (CH 2 O) 4 COO -, CH 3 O (CH 2 O ^{_{) 5 COO -, CH 3 O}} (CH 2 O) 6 COO -, CH 3 O (CH 2 O) 7 COO -, CH 3 O (CH 2 O) 8 COO -, CH 3 O (CH 2 O) 9 _{^{COO -, CH 3 O (CH}} 2 O) 10 COO -,
^{_{CH 3 OCH 2 OSO 3 -,}} CH 3 O (CH 2 O) 2 SO 3 -, CH 3 O (CH 2 O) 3 SO 3 -, CH 3 O (CH 2 O) 4 SO 3 -, CH 3 O _{(CH 2 O) 5 SO 3} -, CH 3 O (CH 2 O) 6 SO 3 -, CH 3 O (CH 2 O) 7 SO 3 -, CH 3 O (CH 2 O) 8 SO 3 -, CH _{3 O (CH 2 O) 9} SO 3 -, CH 3 O (CH 2 O) 10 SO 3 -,

^{_{(CH 3) 2 CHCOO -,}} (CH 3) 2 CHCH 2 COO -, CH 3 CH 2 (CH 3) CHCOO -,
^{_{(CH 3 O) 2 CHCOO -}} , (CH 3 O) 2 CHCH 2 COO -, CH 3 OCH 2 (CH 3) CHCOO -,
^{_{(CH 3 O) 2 CHOCOO -}} , (CH 3 O) 2 CHOCH 2 OCOO -, CH 3 OCH 2 O (CH 3 O) CHOCOO -,
^{_{(CH 3) 2 CHSO 3 -}} , (CH 3) 2 CHCH 2 SO 3 -, CH 3 CH 2 (CH 3) CHSO 3 -,
_{(CH 3 O) 2 CHSO 3} -, (CH 3 O) 2 CHCH 2 SO 3 -, CH 3 OCH 2 (CH 3) CHSO 3 -,
_{(CH 3 O) 2 CH 2} OSO 3 -, (CH 3 O) 2 CH 2 OCH 2 OSO 3 -, CH 3 OCH 2 O (CH 3 O) CHOSO 3 -,
_{^{(COO -) CH 2 COO -}} , (COO -) (CH 2) 2 COO -, (COO -) (CH 2) 3 COO -, (COO -) (CH 2) 4 COO -, (COO -) ( ^{_{CH 2) 5 COO -, (}} COO -) (CH 2) 6 COO -, (COO -) (CH 2) 7 COO -, (COO -) (CH 2) 8 COO -, (COO -) (CH 2 _{^{) 9 COO -, (COO -}} ) (CH 2) 10 COO -,
_{^{(COO -) CF 2 COO -}} , (COO -) (CF 2) 2 COO -, (COO -) (CF 2) 3 COO -, (COO -) (CF 2) 4 COO -, (COO -) ( ^{_{CF 2) 5 COO -, (}} COO -) (CF 2) 6 COO -, (COO -) (CF 2) 7 COO -, (COO -) (CF 2) 8 COO -, (COO -) (CF 2 _{^{) 9 COO -, (COO -}} ) (CF 2) 10 COO -,
_{^{(SO 3 -) CH 2 SO}} 3 -, (SO 3 -) (CH 2) 2 SO 3 -, (SO 3 -) (CH 2) 3 SO 3 -, (SO 3 -) (CH 2) 4 SO _{^{3 -, (SO 3 -)}} (CH 2) 5 SO 3 -, (SO 3 -) (CH 2) 6 SO 3 -, (SO 3 -) (CH 2) 7 SO 3 -, (SO 3 -) ^{_{(CH 2) 8 SO 3 -}} , (SO 3 -) (CH 2) 9 SO 3 -, (SO 3 -) (CH 2) 10 SO 3 -,
_{^{(SO 3 -) (CF 2}} ) CF 2 SO 3 -, (SO 3 -) (CF 2) 2 SO 3 -, (SO 3 -) (CF 2) 3 SO 3 -, (SO 3 -) (CF ^{_{2) 4 SO 3 -, (}} SO 3 -) (CF 2) 5 SO 3 -, (SO 3 -) (CF 2) 6 SO 3 -, (SO 3 -) (CF 2) 7 SO 3 -, ( _{^{SO 3 -) (CF 2)}} 8 SO 3 -, (SO 3 -) (CF 2) 9 SO 3 -, (SO 3 -) (CF 2) 10 SO 3 -,

CH ₃ PO ₄ ^2- , CH ₃ CH ₂ PO ₄ ^2- , CH ₃ (CH ₂ ) ₂ PO ₄ ^2- , CH ₃ (CH ₂ ) ₃ PO ₄ ^2- , CH ₃ (CH ₂ ) ₄ PO ₄ ^{2 -} , CH ₃ (CH ₂ ) ₅ PO ₄ ^2- , CH ₃ (CH ₂ ) ₆ PO ₄ ^2- , CH ₃ (CH ₂ ) ₇ PO ₄ ^2- , CH ₃ (CH ₂ ) ₈ PO ₄ ^2- , CH ₃ (CH ₂ ) ₉ PO ₄ ^2- , CH ₃ (CH ₂ ) ₁₀ PO ₄ ^2- , FCH ₂ PO ₄ ^2- , F (CH ₂ ) ₁₀ PO ₄ ^2- , ClCH ₂ PO ₄ ^2- , Cl (CH ₂ ) ₁₀ PO ₄ ^2- , BrCH ₂ PO ₄ ^2- , Br (CH ₂ ) ₁₀ PO ₄ ^2- , ICH ₂ PO ₄ ^2- , I (CH ₂ ) ₁₀ PO ₄ ^2- ,
CF ₃ PO ₄ ^2- , CF ₃ CF ₂ PO ₄ ^2- , CF ₃ (CF ₂ ) ₂ PO ₄ ^2- , CF ₃ (CF ₂ ) ₃ PO ₄ ^2- , CF ₃ (CF ₂ ) ₄ PO ₄ ^{2 -} , CF ₃ (CF ₂ ) ₅ PO ₄ ^2- , CF ₃ (CF ₂ ) ₆ PO ₄ ^2- , CF ₃ (CF ₂ ) ₇ PO ₄ ^2- , CF ₃ (CF ₂ ) ₈ PO ₄ ^2- , CF ₃ (CF ₂ ) ₉ PO ₄ ^2- , CF ₃ (CF ₂ ) ₁₀ PO ₄ ^2- , FCF ₂ PO ₄ ^2- , F (CF ₂ ) ₁₀ PO ₄ ^2- , ClCF ₂ PO ₄ ^2- , Cl (CF ₂ ) ₁₀ PO ₄ ^2- , BrCF ₂ PO ₄ ^2- , Br (CF ₂ ) ₁₀ PO ₄ ^2- , ICF ₂ PO ₄ ^2- , I (CF ₂ ) ₁₀ PO ₄ ^2- ,
CH ₃ OPO ₄ ^2- , CH ₃ OCH ₂ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₂ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₃ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₄ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₅ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₆ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₇ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₈ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₉ PO ₄ ^2- , CH ₃ O (CH ₂ ) ₁₀ PO ₄ ^2-
CH ₃ OCH ₂ OPO ₄ ^2- , CH ₃ O (CH ₂ O) ₂ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₃ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₄ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₅ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₆ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₇ PO ₄ ^2- , CH ₃ O (CH ₂ O ) ₈ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₉ PO ₄ ^2- , CH ₃ O (CH ₂ O) ₁₀ PO ₄ ^2- ,
(CH ₃ ) ₂ CHPO ₄ ^2- , (CH ₃ ) ₂ CHCH ₂ PO ₄ ^2- , CH ₃ CH ₂ (CH ₃ ) CHPO ₄ ^2- ,
(CH ₃ O) ₂ CHPO ₄ ^2- , (CH ₃ O) ₂ CHCH ₂ PO ₄ ^2- , CH ₃ OCH ₂ (CH ₃ ) CHPO ₄ ^2- ,
(CH ₃ O) ₂ CH ₂ OPO ₄ ^2- , (CH ₃ O) ₂ CH ₂ OCH ₂ OPO ₄ ^2- , CH ₃ OCH ₂ O (CH ₃ O) CHOPO ₄ ^2- ,

^{_{(PO 4 2-) CH 2 COO}} -, (PO 4 2-) (CH 2) 2 COO -, (PO 4 2-) (CH 2) 3 COO -, (PO 4 2-) (CH 2) 4 ^{_{COO -, (PO 4 2-)}} (CH 2) 5 COO -, (PO 4 2-) (CH 2) 6 COO -, (PO 4 2-) (CH 2) 7 COO -, (PO 4 2- ^{_{) (CH 2) 8 COO -}} , (PO 4 2-) (CH 2) 9 COO -, (PO 4 2-) (CH 2) 10 COO -,
^{_{(PO 4 2-) CF 2 COO}} -, (PO 4 2-) (CF 2) 2 COO -, (PO 4 2-) (CF 2) 3 COO -, (PO 4 2-) (CF 2) 4 ^{_{COO -, (PO 4 2-)}} (CF 2) 5 COO -, (PO 4 2-) (CF 2) 6 COO -, (PO 4 2-) (CF 2) 7 COO -, (PO 4 2- ^{_{) (CF 2) 8 COO -}} , (PO 4 2-) (CF 2) 9 COO -, (PO 4 2-) (CF 2) 10 COO -,
^{_{(PO 4 2-) CH 2 SO}} 3 -, (PO 4 2-) (CH 2) 2 SO 3 -, (PO 4 2-) (CH 2) 3 SO 3 -, (PO 4 2-) (CH ^{_{2) 4 SO 3 -, (}} PO 4 2-) -2 4 OP (CH 2) 5 SO 3 -, (PO 4 2-) (CH 2) 6 SO 3 -, (PO 4 2-) (CH 2 ^{_{) 7 SO 3 -, (PO}} 4 2-) (CH 2) 8 SO 3 -, (PO 4 2-) (CH 2) 9 SO 3 -, (PO 4 2-) (CH 2) 10 SO 3 - ,
^{_{(PO 4 2-) CF 2 SO}} 3 -, (PO 4 2-) (CF 2) 2 SO 3 -, (PO 4 2-) (CF 2) 3 SO 3 -, (PO 4 2-) (CF ^{_{2) 4 SO 3 -, (}} PO 4 2-) (CF 2) 5 SO 3 -, (PO 4 2-) (CF 2) 6 SO 3 -, (PO 4 2-) (CF 2) 7 SO 3 ^{_{-, (PO 4 2-) (}} CF 2) 8 SO 3 -, (PO 4 2-) (CF 2) 9 SO 3 -, (PO 4 2-) (CF 2) 10 SO 3 -,
(PO ₄ ^2- ) CH ₂ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₂ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₃ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₄ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₅ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₆ PO ₄ ^2- , (PO ₄ ^2- ) ( (CH ₂ ) ₇ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₈ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₉ PO ₄ ^2- , (PO ₄ ^2- ) (CH ₂ ) ₁₀ PO ₄ ^2- ,
(PO ₄ ^2- ) CF ₂ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₂ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₃ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₄ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₅ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₆ PO ₄ ^2- , (PO ₄ ^2- ) ( CF ₂ ) ₇ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₈ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₉ PO ₄ ^2- , (PO ₄ ^2- ) (CF ₂ ) ₁₀ PO ₄ ^2-

  The anion is preferably a halogen ion, a carboxylate ion, or a sulfonate ion, and includes a fluorine ion, a chlorine ion, a bromine ion, an iodine ion, a laurate ion, a pentafluorobenzenesulfonate ion, and 3,5-trifluoromethylbenzene. A sulfonate ion, a 2,4,6-isopropylbenzene sulfonate ion, a heptafluorobutyrate ion, or an acetate ion is more preferable.

  The sulfonium salt used in the present invention may have one or more asymmetric carbons depending on the type of substituent. Moreover, a sulfur atom may act as an asymmetric center. Any optical isomer in optically pure form based on one or more asymmetric centers, any mixture of the above optical isomers, racemate, diastereoisomer based on two or more asymmetric carbons, above Any antibacterial agent containing any mixture of diastereoisomers as an active ingredient is included in the scope of the present invention. The sulfonium salt having a cation represented by the above formula (I) may form a hydrate or a solvate, and such a case is also included in the scope of the present invention.

  Specific examples of preferred sulfonium salts include the following sulfonium salts, but the sulfonium salts used in the antibacterial agent of the present invention are not limited to the following specific sulfonium salts.

  The sulfonium salt represented by the above formula (I) can be obtained as a commercial product, or known methods such as the method described in J. Am. Chem. Soc., 97, 1188 (1975), J. Am. The method described in Chem. Soc., 73, 1965 (1951), the method described in Chem. Pharm. Bull., 29, 3753 (1981), etc., is used to form a sulfonium ion, which is facilitated by salt exchange with the desired anion. Can be synthesized.

  You may use said sulfonium salt as an antibacterial agent of this invention as it is. Alternatively, an antibacterial composition is prepared and used in combination with the above sulfonium salt and one or more additives such as a suitable carrier and adjuvant, more specifically a surfactant, binder, or stabilizer. You can also. Examples of antibacterial compositions include compositions in the form of powders, wettable powders, emulsions, liquids, flowables (sols), granules, aerosols, solids, coatings, etc. It is not limited to. The antibacterial agent of the present invention is preferably used for uses other than administration to humans, more preferably for uses other than administration to humans or mammals, and more preferably for industrial use. Administration to humans or mammals means, for example, oral or parenteral administration for the purpose of preventing and / or treating infectious diseases.

  In the present specification, industrial use means a use excluding administration to humans or mammals, and preferably a use excluding application to organisms such as fish and plants for food and ornamental use. More preferably, it means a use excluding addition to foods (including processed foods produced in factories, etc.) intended to be consumed or consumed by humans or mammals. The antibacterial agent of the present invention is preferably used by being added to or brought into contact with industrial raw materials or products. Although a contact means is not specifically limited, For example, means, such as application | coating or spraying, are employable. Further, the antibacterial agent of the present invention may be used for disinfection, for example, for disinfection of human hands. The industrial raw material or product to which the antibacterial agent of the present invention is applied is preferably a material or product containing natural and synthetic organic substances, and particularly preferably a material or product containing natural and synthetic polymer compounds. Examples include paint, ink, adhesive, glue, cloth, paper, fiber, pulp, chip, wood, plastic, rubber, leather, metalworking oil, and the like. The concentration of the sulfonium salt, which is an active ingredient when applied to or sprayed on an industrial product, is not particularly limited, but is preferably in the range of 0.00001 to 10% (mass%, the same shall apply hereinafter), more preferably 0.001 to 10%. It is a range. Moreover, when adding to industrial products, it is preferable to add so that the density | concentration of the sulfonium salt which is an active ingredient may be 0.00001-10%, Preferably it is the range of 0.001-10%.

  The carrier that can be used in the antibacterial agent of the present invention may be either solid or liquid as long as it is commonly used as a carrier contained in an antibacterial composition, and is not limited to a specific carrier. For example, as a solid carrier, mineral powder (kaolin, bentonite, clay, montmorillonite, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phosphorus, lime, white carbon, slaked lime, quartz sand, ammonium sulfate, urea, etc.), vegetable powder (Soy flour, wheat flour, wood flour, starch, crystalline cellulose, etc.), alumina, silicate, sugar polymer, highly dispersible silicic acid, waxes and the like can be mentioned. Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene). , Cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, trichlorofluoromethane, dichlorodifluoromethane, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.), Ketones (acetone, methyl ethyl ketone, cyclohexane, methyl isobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, dioctyl phthalate) , Amyl acetate, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, 1-methoxy-2-propanol) ), Amines (ethylamine, dimethylamine, trimethylamine, isobutylamine, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), industrial gasoline (petroleum ether, solvent naphtha, etc.), and petroleum And fractions (paraffins, kerosene, light oil, etc.).

  In addition, when the antibacterial composition of the present invention is prepared in the form of powder, emulsion, wettable powder, sol (flowable agent), granule, aerosol, solid agent, or coating agent, emulsification, dispersion, For the purposes of solubilization, wetting, foaming, spreading, etc., it is preferable to use a surfactant. Examples of such surfactants include nonionic type (polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester, sorbitan alkyl ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil). , Polyoxyethylene polyoxypropylene glycol, etc.), anionic type (alkylbenzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic type (alkylamine salt (laurylamine, stearyltrimethyl) Ammonium chloride, alkyldimethylbenzylammonium chloride), deoxycholate, etc.), amphoteric type (carboxylic acid (betaine type), Ester, etc.), and the like, but not limited thereto.

  In addition, auxiliary agents such as polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC), gum arabic, polyvinyl acetate, gelatin, casein, and sodium alginate can be added to the antibacterial composition of the present invention. Furthermore, an appropriate amount of a stabilizer such as an antioxidant or an ultraviolet absorber can be added as necessary. The antibacterial composition of the present invention may be used by mixing with other antibacterial agents. Also, two or more kinds of sulfonium salts which are active ingredients can be used in combination. In the antibacterial agent or antibacterial composition of the present invention, the content of the sulfonium salt that is an active ingredient is not particularly limited, but when a single sulfonium salt or two or more sulfonium salts are used, the total content thereof is powder, hydrated In the case of agents, emulsions, solutions, flowables, and granules, it is 0.00001 to 100%, preferably 0.001 to 100% (100% means that the sulfonium salt which is an active ingredient is used as it is).

Since the antibacterial agent of the present invention has a high antibacterial effect and low mutagenicity, it can be used for the following applications, but the application is not limited to the applications exemplified below.
(1) Prevention of spoilage problems due to bacterial growth during the manufacturing process, storage and use of water-based or oil-based paints, and prevention of bacterial contamination on the painted surface after painting.
(2) Prevention of spoilage problems caused by the growth of bacteria such as casein, polyvinyl alcohol, starch and other adhesives or paste, and bacterial contamination on the coating adhesion surface.
(3) Prevention of quality deterioration failure due to bacterial growth during storage of papermaking raw materials such as wet pulp and chips.
(4) Prevention of contamination and quality degradation failures due to bacterial growth on processed products and materials such as wood, plywood, bamboo, leather, tatami, joints and tiles.
(5) Prevention of contamination and deterioration of quality due to bacterial growth on natural fibers, synthetic fibers and their blended products and materials.
(6) Prevention of quality deterioration failure due to bacterial growth in synthetic emulsion or emulsion wax.
(7) Prevention of quality deterioration failure due to growth of bacteria in preparations using surfactants.
(8) Prevention of quality deterioration failures due to bacterial growth in hydraulic fluids.
(9) Preventing deterioration of quality due to bacterial growth in plastics, rubber, etc. or antibacterial.
(10) Control of slime damage caused by bacteria during the papermaking process.
(11) Sterilization and disinfection of hospitals, clinics, dental clinics, health facilities, visiting care, osteopathic clinics, acupuncture clinics, massages, animal hospitals, pet shops, nail salons, poultry houses, and the skin and fingers of workers.

  In this specification, the term antibacterial means the killing of microorganisms or the inhibition of the growth of microorganisms. The microorganisms targeted by the antibacterial agent of the present invention are not particularly limited, and include bacteria (including all bacteria including gram positive or gram negative bacteria, aerobic or anaerobic bacteria, etc.), fungi (yeast, filamentous fungi), etc. In addition, mutant strains of these microorganisms are included. The bactericidal agent of the present invention can be used for bactericidal or bacteriostatic of any one or more microorganisms. For example, the bacteria listed in the Bergey's Manual of Bacteriology (RGE Murray et al., Williams & Wilkins, 1984) can be cited as bacteria that are the target of the antibacterial agent of the present invention. The fungi listed in Shunichi Udagawa et al., Kodansha, 1986) can be mentioned, but are not limited to these.

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the scope of the present invention is not limited to these examples.
The sulfonium salts used in the examples are commercially available from Sigma-Aldrich Co. (St. Louis, MO USA) or known methods (eg J. Am. Chem. Soc., 97, 1188 ( 1975), J. Am. Chem. Soc., 73, 1965 (1951), Chem. Pharm. Bull., 29, 3753 (1981). And a method of salt exchange with an anion).

Example 1: Evaluation of mutagenicity
10 ml of culture solution (NUTRIENT BROTH No.2, Lot / Ch.-B .: 276098, OXOID) was dispensed into L-shaped tubes (capacity: 23 ml) and stored frozen (below -80 ° C) 10 20 μl of a dimethylsulfoxide (hereinafter referred to as DMSO) suspension (bacterial concentration: about 10 ⁸ CFU / ml) was inoculated. As test bacteria, Salmonella typhimurium TA100, TA 98, TA 1535, TA 1537 (above, sold by Prof. Bruce N. Ames, University of California-Berkeley, Div. Biochem. & Molecular Biology) and Escherichia coli WP2 uvrA Five strains (distributed from the Department of Mutational Genetics, National Institute of Health Sciences) were used.

The culture solution inoculated with the fungus was shaken and cultured at 37 ° C for 10 hours (100 spm), and then the absorbance (660 nm) of the bacterial solution was measured. From the relationship between the bacterial concentration and absorbance (660 nm) determined in advance, After confirming that the concentration was 1 × 10 ⁹ CFU / ml, the bacterial suspension was subjected to the test. The bacterial suspension was subjected to the test within 1 hour after preparation.
The test substance concentration was 50 mg / ml as the maximum dose, and dissolved in DMSO so that there were 5 levels including the maximum dose at a dilution rate of 4 times to prepare a test substance solution. When 0.1 ml of this test substance solution is used for metabolic activation, 0.5 ml of S9mix (0.1 ml of S9 (Kikkoman), MgCl ₂ 8 μmol, KCl 33 μmol, glucose-6-phosphate 5 μmol, NADPH 4 μmol, NADH 4 μmol, sodium-phosphorus) Prepare 1 ml of acid buffer (100 μmol, sterilized distilled water), and add 0.5 ml of 1M sodium-phosphate buffer, and then add 0.1 ml of bacterial suspension when not using metabolic activation. . Then add 2 ml of agar solution (Bacto Agar, BECTONDICKINSON) kept at 50 ° C after warming, stir and overlay on minimal glucose agar plate (Kurimedia, Oriental Yeast) for 48 hours at 37 ° C. Cultured.
Simultaneously with the test substance test, only the solvent (DMSO) was added instead of the test substance solution to make a negative control, and the compounds listed in Table 1 were added instead of the test substance to make a positive control.

AF-2 (Wako special grade, purity 99.1%), NaN ₃ (chemical, purity 99.8%), B [a] P (Wako special grade, purity 100%) and 2- AA (no grade setting, purity 96.6%) was purchased from Wako Pure Chemical Industries, Ltd. 9-AA (no grade set, purity 98%) was purchased from Aldrich Chemical Co., Inc.

  The mutagenicity of the test substance was evaluated by measuring the number of revertant colonies observed on the cultured plate medium according to the test substance concentration according to the Ames test (mutation test using bacteria). When the measured number of revertant colonies increases in a dose-dependent manner and the number of revertant colonies is more than twice that of the revertant colonies in the negative control (natural revertant colonies), the mutagenicity is positive. A case where the number of revertant colonies was less than twice the number of revertant colonies in the negative control (natural revertant colonies) was determined as negative. If dose-dependence was not observed even though an increase in the number of reverse mutant colonies was observed, a retest was conducted to determine the reproducibility of the results and the mutagenicity was determined.

In order to compare the antibacterial properties and the mutagenicity of the general-purpose antibacterial agent and the antibacterial agent of the present invention using the above method, the general-purpose antibacterial agents creosote oil, orthophenylphenol, and glutaraldehyde, and the antibacterial agent of the present invention The sulfonium salts represented by the above formulas (II) to (IV) were evaluated as agents. The results are shown in Table 2.
As can be seen from Table 2, regarding the mutagenicity, orthophenylphenol and glutaraldehyde were positive among the general-purpose antibacterial agents, but both of the antibacterial agents of the present invention were negative.

Example 2: Evaluation of antibacterial activity (1)
A 20 ml sensitivity measurement bouillon (manufacturing number 026307, Nissui Pharmaceutical Co., Ltd.) in a 100 ml Erlenmeyer flask was inoculated with one platinum loop of the test bacteria stored at room temperature. Test bacteria are Staphylococcus aureus subsp.aureus (NRBC No. 15035) (hereinafter referred to as S. sureus), Bacillus subtilis subsp.subtilis (NRBC No. 13719)) (hereinafter referred to as B. subtilis), Escherichia coli (NRBC No. 15034)) (hereinafter referred to as E. coli) and Pseudomonas aeruginosa (NRBC No. 13275)) (hereinafter referred to as P. aeruginosa). All the above four strains were obtained from National Institute of Technology and Evaluation.
The culture solution inoculated with the fungus is shaken and cultured at 30 ° C for 24 hours (80 strokes / min), and the cultured suspension is diluted with Mula Hinton broth (Lot 4026912, Becton, Dickinson and Company). 10 ⁶ / ml bacterial suspension was prepared.

For each test substance represented by the formulas (II) to (XII) listed below, the maximum concentration is 318 μM, respectively, and diluted with Mueller Hinton broth so that there are 12 levels including the maximum concentration at a dilution factor of 2 each. A test substance solution was prepared. Dispense 50 μl of the test substance solution into a 96-well microplate, and dispense 50 μl of the approximately 10 ⁶ cells / ml bacterial suspension prepared above into a 96-well microplate containing the test substance solution. The mixture was stirred with a plate shaker (manufactured by BEMarubisi) to give a test solution. The bacterial suspension was subjected to the test within 20 minutes after preparation. (The final concentration of the test substance is 318 μM with a maximum concentration of 12 times including the maximum concentration at a dilution factor of 2 and the final concentration of the bacteria is about 10 ⁵ cells / ml).
A system in which the test substance and bacteria are not added is used as a solvent control, and gentamicin sulfate (purity 82% or more, Wako Pure Chemical Industries, Ltd.) is used instead of the test substance as a control for confirming the test accuracy. Each time, these solvent controls and gentamicin were added for testing. However, the final concentration of gentamicin sulfate was set at 12 levels including 12.5 ppm as the maximum concentration and the maximum concentration at a dilution factor of 2 each.

The prepared test solution was incubated at 30 ° C. for 24 hours. Then, the absorbance (630 nm) is measured with a microplate reader (Microplate Bio-kinetics Reader, BIO-TEK Instruments). If the absorbance of the system to which the test substance is added is less than twice that of the solvent control, the growth of the bacteria Was determined to be the lowest concentration at which growth was suppressed for each test substance, and was defined as the minimum growth inhibitory concentration (hereinafter abbreviated as MIC). Each test substance was tested twice or more, and the highest MIC in each test was defined as the MIC of the test substance. The results are shown in Table 3.
ClogP of the cation of the sulfonium salt was calculated based on the chemical structural formula of each compound using clogptalk 4.82 (trademark) (Daylight CIS Inc.) which is an automatic calculation software.

  As can be seen from Table 3, the sulfonium salt (ClogP: 10.1 to 16.5) according to the present invention represented by the formulas (II) to (VI) has a MIC of at least two of the four types of bacteria subjected to the test. Although the sulfonium salt other than the present invention represented by the formulas (VII) to (XII) (comparative example, ClogP: -1.7 to 2.2) represented by the formulas (VII) to (XII) had a MIC of 318 μM for all four types of bacteria subjected to the test. Became higher. Therefore, it was shown that the sulfonium salt which is an active ingredient of the antibacterial agent of the present invention has stronger antibacterial activity than the sulfonium salts other than the present invention.

Example 3: Evaluation of antibacterial activity (2)
Test bacteria (Table 4) were pre-cultured under the conditions shown in Table 5 and suspended at a predetermined concentration to obtain a test bacteria solution. The test bacteria (8) to (10) (filamentous fungi) were filtered through absorbent cotton to remove the mycelia, and 10 ⁵ CFU / ml bacterial solution was prepared in the form of spores. The number of bacteria in the test bacterial solution was measured under the conditions shown in Table 6 by the flat plate smearing method.
Prepared by dissolving the compound of formula (IV) and the highest concentration solution of benzalkonium chloride in anhydrous DMSO (Wako Pure Chemical Industries) according to Table 7, and doubled in anhydrous DMSO (Wako Pure Chemical Industries) A dilution series was prepared in 10 steps including the highest concentration. 10 μl of each prepared dilution series was dispensed in two series into a test tube containing 1 ml of the medium shown in Table 8.
For the test bacterium (7), 50 μl of each compound dilution series was added to 5 ml of warm-dissolved medium containing 1.5% agar and stirred, and then solidified at room temperature to prepare an agar plate.
25 μl of the bacterial solution shown in Table 7 was added to a dilution series of compounds dispensed in 1 ml, and cultured under the conditions shown in Table 8. For the test bacteria (7), about 10 μl of the bacterial solution was smeared on an agar plate using a platinum loop and cultured under the conditions shown in Table 8. In addition, the test bacteria were inoculated into a medium containing no compound and cultured under the conditions shown in Table 8 as a control for confirming the growth of the bacteria.
After culturing, the presence or absence of growth of the test bacteria was determined with the naked eye, and the lowest concentration at which bacterial growth was not observed was determined as MIC.

As can be seen from Table 9, the sulfonium salt of the present invention represented by the formula (IV) (ClogP: 13.3) is general-purpose for all seven types of bacteria, three types of filamentous fungi, and three types of yeast used in the test. The MIC was lower than that of the antibacterial agent benzalkonium chloride, that is, the antibacterial property was superior to that of the general-purpose antibacterial agent benzalkonium chloride.
The MIC ratio (the value obtained by dividing the MIC of benzalkonium chloride by the MIC of the sulfonium salt according to the present invention represented by the formula (IV)) is 4.4 to 33 for bacteria, 1.6 to 9.9 for filamentous fungi, and 3.6 to 3.6 for yeast. 30. That is, when MIC is used as an index, the sulfonium salt according to the present invention represented by the formula (IV) is 4.4 to 33 times in bacteria and 1.6 to 9.9 in filamentous fungi compared to benzalkonium chloride which is a general-purpose antibacterial agent. The antibacterial activity was 3.6 to 30 times higher in yeast.

Claims (5)

An antibacterial agent containing a sulfonium salt as an active ingredient, wherein the cation of the sulfonium salt has the following structure:

{Wherein W ₃ represents _three Ws bonded to a sulfur atom, and the three Ws may be the same or different from each other, and each independently represents an alkyl group having 7 to 11 carbon atoms} And the antibacterial agent whose ClogP of the cation of this sulfonium salt is 7 or more and less than 18. The antibacterial agent according to claim 1, wherein ClogP of the cation of the sulfonium salt is 9 or more and less than 16. The antibacterial agent according to claim 1, wherein ClogP of the cation of the sulfonium salt is 11 or more and less than 14. The antibacterial agent according to any one of claims 1 to 3, wherein the value of ClogP is a value calculated by automatic calculation software clogptalk 4.82 (trademark) . An antibacterial composition comprising the sulfonium salt according to any one of claims 1 to 3 and one or more additives.