JP5703381B2 - ジブロモマロンアミドの組成物および殺生物剤としてのその使用 - Google Patents
ジブロモマロンアミドの組成物および殺生物剤としてのその使用 Download PDFInfo
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- JP5703381B2 JP5703381B2 JP2013531547A JP2013531547A JP5703381B2 JP 5703381 B2 JP5703381 B2 JP 5703381B2 JP 2013531547 A JP2013531547 A JP 2013531547A JP 2013531547 A JP2013531547 A JP 2013531547A JP 5703381 B2 JP5703381 B2 JP 5703381B2
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- 230000003115 biocidal effect Effects 0.000 title claims description 42
- 239000000203 mixture Substances 0.000 title claims description 27
- SWHQVMGRXIYDSF-UHFFFAOYSA-N 2,2-dibromopropanediamide Chemical group NC(=O)C(Br)(Br)C(N)=O SWHQVMGRXIYDSF-UHFFFAOYSA-N 0.000 title claims description 26
- 239000003139 biocide Substances 0.000 title description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 244000005700 microbiome Species 0.000 claims description 18
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 claims description 17
- 239000012530 fluid Substances 0.000 claims description 13
- SKDNDVDHYMEGNJ-UHFFFAOYSA-N (2-bromo-2-nitroethenyl)benzene Chemical compound [O-][N+](=O)C(Br)=CC1=CC=CC=C1 SKDNDVDHYMEGNJ-UHFFFAOYSA-N 0.000 claims description 12
- DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 12
- 230000000813 microbial effect Effects 0.000 claims description 12
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- 244000063299 Bacillus subtilis Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
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- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
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- 239000000498 cooling water Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
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- 230000010534 mechanism of action Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 239000012266 salt solution Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/48—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A—HUMAN NECESSITIES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/42—Amides
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- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
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Description
第2の形態においては、本発明は水性または水含有システムにおける微生物を抑制する方法を提供する。この方法は、有効量の本明細書において記載される殺生物組成物でこのシステムを処理することを含む。
このアッセイは活性物質間の相乗効果の予備的な評価として使用される。手順は以下の通りである。無機塩溶液(1Lの水中の0.2203gのCaCl2、0.1847gのMgSO4、および0.2033gのNaHCO3、pH約8)に、同量(約100CFU/ml)のシュードモナスアエルギノーサATCC 10045、および黄色ブドウ球菌ATCC 6538の混合物が接種された。次いで、この細胞懸濁液のアリコートが2,2−ジブロモマロンアミド(DBMAL)、求電子部分含有殺生物剤、およびそれらの組み合わせで、様々な濃度レベルで処理された。37℃で2時間インキュベートした後で、このアリコートにおけるバクテリア細胞を完全に殺すのに必要とされる最小殺生物剤濃度(MBC)に基づいて、殺生物有効性が決定される。このMBC値は、次いで、相乗指数(SI)値を計算するために使用される。
相乗指数=MDBMAL/CDBMAL+MB/CB
式中、
CDBMAL:単独で使用される場合に、バクテリアの成長を阻止するのに必要なDBMALの濃度。
CB:単独で使用される場合に、バクテリアの成長を阻止するのに必要な殺生物剤(B)の濃度。
MDBMAL:殺生物剤(B)と組み合わせて使用される場合に、バクテリアの成長を阻止するのに必要なDBMALの濃度。
MB:DBMALと組み合わせて使用される場合に、バクテリアの成長を阻止するのに必要な殺生物剤(B)の濃度。
SI<1:相乗的組み合わせ
SI=1:相加的組み合わせ
SI>1:拮抗的組み合わせ
実施例において使用される成長阻止アッセイは微生物集団の成長の阻止(またはその欠失)を測定する。成長の阻止は、細胞を殺すこと(すなわち、成長が起こらない)、再増殖に長時間を必要とするように細胞の集団のかなりの部分を殺すこと、または殺すことなく成長の阻止(静止状態)の結果であり得る。作用のメカニズムに関係なく、殺生物剤(または殺生物剤の組み合わせ)の影響は群落のサイズの増大に基づいて時間の経過とともに測定されうる。
相乗指数=MDBMAL/CDBMAL+MB/CB
式中、
CDBMAL:単独で使用される場合に、バクテリアの成長を〜90%阻止するのに必要なDBMALの濃度。
CB:単独で使用される場合に、バクテリアの成長を〜90%阻止するのに必要な殺生物剤(B)の濃度。
MDBMAL:殺生物剤(B)と組み合わせて使用される場合に、バクテリアの成長を〜90%阻止するのに必要なDBMALの濃度。
MB:DBMALと組み合わせて使用される場合に、バクテリアの成長を〜90%阻止するのに必要な殺生物剤(B)の濃度。
SI<1:相乗的組み合わせ
SI=1:相加的組み合わせ
SI>1:拮抗的組み合わせ
DBMALおよびブロノポール
キルアッセイ結果
表2はDBMALを単独で、および2−ブロモ−2−ニトロプロパン−1,3−ジオール(「ブロノポール」または「BNPD」)との組み合わせで用いたアッセイについての結果をまとめる。この結果はこれら活性物質間の相乗効果を示す(表2)。
表3は、DBMAL、THPSおよび組み合わせについての成長阻止アッセイ結果を示す。このアッセイにおいては、集団の成長が対照よりも少なくとも90%小さい(I90値)DBMALの最小濃度が12.5mg/lである。ブロノポールのI90値は6.25mg/mlである。
DBMALおよびBNS
成長阻止アッセイ結果
表5はDBMAL、ブロモニトロスチレン(BNS)、およびこれらの組み合わせについての成長阻止アッセイ結果を示す。DBMALおよびBNSについてのI90値はそれぞれ12.5mg/lおよび6.25mg/lである。
DBMALおよびMBT
成長阻止アッセイ結果
表7はDBMAL、メチレンビス(チオシアナート)(MBT)、および組み合わせについての成長阻止アッセイ結果を示す。DBMALおよびMBTについてのI90値はそれぞれ12.5mg/lおよび0.78mg/lである。
DBMALおよびDBDCB
成長阻止アッセイ結果
表9はDBMAL、1,2−ジブロモ−2,4−ジシアノブタン(DBDCB)、およびそれらの組み合わせについての成長阻止アッセイ結果を示す。DBMALおよびDBDCBについてのI90値は6.25mg/lである。
Claims (7)
- 水性または水含有システムにおいて微生物を抑制するための殺生物組成物であって、
a.2,2−ジブロモマロンアミドおよび2−ブロモ−2−ニトロプロパン−1,3−ジオール、ここで、2,2−ジブロモマロンアミド:2−ブロモ−2−ニトロプロパン−1,3−ジオールの重量比は、32:1〜1:2である、
b.2,2−ジブロモマロンアミドおよびブロモニトロスチレン、ここで、2,2−ジブロモマロンアミド:ブロモニトロスチレンの重量比は、32:1〜1:2である、
c.2,2−ジブロモマロンアミドおよびメチレンビス(チオシアナート)、ここで、2,2−ジブロモマロンアミド:メチレンビス(チオシアナート)の重量比は、32:1〜4:1である、または
d.2,2−ジブロモマロンアミドおよび1,2−ジブロモ−2,4−ジシアノブタン、ここで、2,2−ジブロモマロンアミド:1,2−ジブロモ−2,4−ジシアノブタンの重量比は、8:1〜2:1である
を含む殺生物組成物。 - 前記組成物が、2,2−ジブロモマロンアミドおよび2−ブロモ−2−ニトロプロパン−1,3−ジオールを含み、かつ2,2−ジブロモマロンアミド:2−ブロモ−2−ニトロプロパン−1,3−ジオールの重量比が32:1〜2:1である請求項1に記載の組成物。
- 前記組成物が塗料、コーティング剤、水性エマルション、ラテックス、接着剤、インク、顔料分散物、家庭用または産業用クリーナー、洗浄剤、食器洗浄剤、鉱物スラリー、ポリマーエマルション、コーキング剤、接着剤、テープジョイントコンパウンド、消毒剤、サニタイザー、金属加工用流体、建築用品、パーソナルケア製品、織物用流体、スピン仕上げ剤、産業プロセス水、油田用機能液、燃料、エアウォッシャー、排水、バラスト水、ろ過システム、水泳用プール、または温泉水である、請求項1または2に記載の組成物。
- 有効量の請求項1〜3のいずれか1項に記載の組成物で水性または水含有システムを処理することを含む、水性または水含有システムにおける微生物の成長を抑制する方法。
- 前記水性または水含有システムが塗料、コーティング剤、水性エマルション、ラテックス、接着剤、インク、顔料分散物、家庭用または産業用クリーナー、洗浄剤、食器洗浄剤、鉱物スラリー、ポリマーエマルション、コーキング剤、接着剤、テープジョイントコンパウンド、消毒剤、サニタイザー、金属加工用流体、建築用品、パーソナルケア製品、織物用流体、スピン仕上げ剤、産業プロセス水、油田用機能液、燃料、エアウォッシャー、排水、バラスト水、ろ過システム、水泳用プール、または温泉水である請求項4に記載の方法。
- 前記組成物が水性または水含有システムにおける微生物の成長を阻止する、請求項4または5に記載の方法。
- 前記組成物が水性または水含有システムにおける微生物を殺す、請求項4または5に記載の方法。
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CN112868650A (zh) * | 2021-02-03 | 2021-06-01 | 山东华特水处理科技有限公司 | 一种杀菌剂及其制备方法和应用 |
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