JP5398177B2 - 殺菌性組成物 - Google Patents
殺菌性組成物 Download PDFInfo
- Publication number
- JP5398177B2 JP5398177B2 JP2008147463A JP2008147463A JP5398177B2 JP 5398177 B2 JP5398177 B2 JP 5398177B2 JP 2008147463 A JP2008147463 A JP 2008147463A JP 2008147463 A JP2008147463 A JP 2008147463A JP 5398177 B2 JP5398177 B2 JP 5398177B2
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- JP
- Japan
- Prior art keywords
- acid
- compound
- bactericidal
- present
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006174 synthetic rubber latex Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
上記アルキル基は、直鎖アルキル基、分岐アルキル基のいずれであってもよいが、本発明では直鎖アルキル基が好適である。
また、本発明化合物を塩とした場合、イミダゾール環の窒素原子上の非共有電子対にプロトンが配位し、分子が陽電荷を帯びた状態になるものと考えられる。当該化合物の多くが陽イオンとして存在することにより、微生物を構成するリン脂質やタンパク質との相互作用が高まり、殺菌効果が向上することも期待できる。
このような塩は、[化3]に示す構造で表すことができる。なお、Xn−は有機性または無機性のアニオン基であり、nは整数である。
このような塩は、慣用的な化学合成法によって合成することができる。具体的には、水中または有機溶媒中、あるいはこれらの混合溶媒中において、1当量以上の酸とヒドロキシアルキルイミダゾール化合物を反応させる方法等により合成できる。この際、過剰な酸を真空下で除去してもよいし、イオン交換樹脂を用いてアニオン基を交換することも可能である。
20mmolの2−ヒドロキシメチルイミダゾールを30mlのDMF(N,N−ジメチルホルムアミド)に溶解させ、さらに30mmolのナトリウムメトキシドを加え、窒素雰囲気下にて、加熱しながら攪拌した。溶液の色に変化が認められた後に、40mmolの臭化アルキルを滴下し、還流させながら5時間攪拌を行った。反応停止後、反応液をろ過し、沈殿物を除去した後に、減圧蒸留にて溶媒を留去した。残渣をシリカゲルカラムクロマトグラフィー(ジクロロメタン:メタノール=20:1)にて精製を行い、TLC(ジクロロメタン:メタノール=10:1)にて、スポットがRf=0.5〜0.7に現れる画分を集め、濃縮し、前記[化2]に示す殺菌性化合物を得た。
上記方法で得られた8種の殺菌性化合物、及びOIT(2‐n−オクチル‐4‐イソチアゾリン‐3‐オン)について、以下の試験を実施し、殺菌性を評価した。
クロラムフェニコールを添加したポテトデキストロース寒天平板培地の中央に、上記試験片を静置した。次いで、スルホこはく酸ジオクチルナトリウム50mlを蒸留水に添加し、オートクレーブした滅菌水に、カビ胞子を5白金耳加え、ガーゼでろ過した胞子懸濁液を、上記寒天培地に1ml滴下し、28℃に設定したインキュベーターにて1週間培養を行った。カビ胞子としては、表1に示すものをそれぞれ使用した。
◎:試験片上に菌糸の伸長が認められない
○:試験片の1/3未満に菌糸の伸長が認められる
△:試験片の1/3以上2/3未満に菌糸の伸長が認められる
×:試験片の2/3以上に菌糸の伸長が認められる
Claims (1)
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DE4309690A1 (de) * | 1993-03-25 | 1994-09-29 | Bayer Ag | Anstrichmittel |
WO1995014383A1 (de) * | 1993-11-24 | 1995-06-01 | Bayer Aktiengesellschaft | Alkyl-n-azole |
FR2732017B1 (fr) * | 1995-03-21 | 2000-09-22 | Inst Nat Sante Rech Med | Nouveaux derives de l'imidazole antagonistes et/ou agonistes du recepteur h3 de l'histamine, leur preparation et leurs applications therapeutiques |
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