JPS6243966B2 - - Google Patents
Info
- Publication number
- JPS6243966B2 JPS6243966B2 JP4354481A JP4354481A JPS6243966B2 JP S6243966 B2 JPS6243966 B2 JP S6243966B2 JP 4354481 A JP4354481 A JP 4354481A JP 4354481 A JP4354481 A JP 4354481A JP S6243966 B2 JPS6243966 B2 JP S6243966B2
- Authority
- JP
- Japan
- Prior art keywords
- synergistic effect
- compound
- mic
- alone
- present
- 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
Links
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical class ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 5
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Chemical class 0.000 claims description 4
- 239000002184 metal Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 238000003113 dilution method Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000750 industrial fungicide Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- 229940116368 1,2-benzisothiazoline-3-one Drugs 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Description
本発明は、2−メルカプトピリジン−N−オキ
シドまたはその金属塩、および1・2−ベンズイ
ソチアゾリン−3−オンを有効成分として含有す
ることを特徴とする工業用殺菌剤に関する。
本発明の上記2成分から成る工業用殺菌剤は、
各々の成分の抗菌スペクトルを保持したまま、抗
菌作用のより強い相乗効果をもたらすものであ
る。
水系有機システムの殆んどすべての物は微生物
に侵害される傾向があり、そのような侵害をうけ
ると不快な臭気や懸濁を生じ、エマルジヨンの分
解、分散液の凝固、粘度低下、PHの変化、スライ
ムの形成など、種々の弊害を生じ、その製品の商
品価値を大きく低下させたりする。
たとえば、石油化学工場または化学工場などで
用いられている循環冷却方式の熱交換器や排水、
冷却管などにスライムが発生し、パイプを閉塞し
て冷却効率を低下させたり、あるいは製紙工場に
おいて白水に発生した微生物が泥状のスライムを
形成してこれが剥離して紙に混入すると、巻取り
工程で紙を切断させたり、紙に斑点ができたり、
不快臭が生じたり、各種のトラブルを引き起こす
ものである。
本発明の活性成分の1つである2−メルカプト
ピリジン−N−オキシドの金属塩としては、アル
カリ金属、アルカリ土類金属および亜鉛塩などが
あり、たとえばナトリウム、カリウム、カルシウ
ム、マグネシウム、亜鉛塩があげられるがこれら
に限定されるものではない。
本発明者らは、これらの第1成分単独の場合よ
り強い抗菌力を有し、かつ、持続的な効果を示す
薬剤の組合わせについて鋭意研究を重ねた結果、
第2の成分として1・2−ベンズイソチアゾリン
−3−オンを併用することにより、相乗的に抗菌
力が高められ接続的な効果を示すことを見い出し
た。すなわち、本発明者らは、これらの2成分を
併用することにより、殆んどの被殺菌対象物に対
し効果が期待でき、かつそれぞれ単独使用の場合
における殺菌作用より強力な、換言すれば、単独
使用時の薬剤量の何分の1かの量で同様な効果を
発揮する産業上極めて顕著な相乗効果を見い出
し、本発明を完成するに至つた。
2−メルカプトピリジン−N−オキシドまたは
その金属塩と1・2−ベンズイソチアゾリン−3
−オンを好ましくは32:1〜1:128重量比(一
般に特に好ましくは1:1〜1:4の場合に強力
な相乗作用を示す。)の割合で混合した混合薬剤
を数ppmの濃度で用いれば充分菌の生育を阻止
できることが明らかになつた。また、2成分を併
用することにより相乗作用を示すことから、薬剤
量の大幅な削減が可能となり、その分コストも安
くなつて実用上大きなメリツトをもたらすことに
なつた。
実際の使用に際しては、本発明成分を親水性有
機溶媒(ジメチルホルムアミド、エチレングリコ
ール、メチルセルソルブなど)に溶解させて溶液
(場合によつてはポリオキシエチレンアルキルア
ミン、アルキロールアミンなどの界面活性剤も添
加して均一化させる。)とした後、系にそれらを
添加することによつて微生物の増殖を防止するこ
とが可能である。
次に本発明を完成するのに使用した2成分の相
乗効果試験方法について説明する。
相乗作用効果試験方法
2成分間の相乗作用を二元希釈法により測定す
る。両成分を所定の濃度になるように希釈し、ブ
イヨン培地にそれぞれ一定量添加する。次に、予
め前培養した菌液の一定量を接種し、37℃にて
6.5時間振盪培養した後、660nmでの吸光度増加
が認められない両成分濃度を二元希釈法による最
小発育阻止濃度(以下、TDMICという。)とす
る。
第1図は普通目盛座標を用いて、それぞれの成
分の最小発育阻止濃度(以下、MICという。)を
両軸上に等しくとつたグラフである。このグラフ
では、曲線(すなわち、TDMIC曲線)より上側
の領域は増殖阻止域を示し、下側の領域は増殖域
を示す。また、対角線とTDMIC曲線が一致する
ときは相加作用を、対角線より上側にTDMIC曲
線があるときは拮抗作用を、下側にあるときは相
乗作用を表わす。
つぎに、実施例により本発明を説明する。
なお、実施例中、化合物Aは2−メルカプトピ
リジン−N−オキシドのナトリウム塩を、化合物
Bは1・2−ベンズイソチアゾリン−3−オンを
意味する。
実施例 1
シユードモナス・エルギノーサに対する相乗効
果
化合物Aおよび化合物Bをそれぞれ100μg/
mlより倍数希釈して調製の後、前記試験方法に準
じて相乗効果を検討した。
その結果を、第2図に示す。図より、このシユ
ードモナス・エルギノーサに対するTDMIC曲線
は明らかに著しい相乗作用を意味するものであ
る。菌の生育を完全に抑制した2成分の相乗効果
は、たとえば、化合物Aの濃度が12.5μg/ml
で、化合物Bの濃度が3.2μg/mlである場合に
現われた。すなわち、この薬剤濃度は、化合物A
単独のMICの1/8であり、化合物B単独のMIC
の約1/16の量であることから、この薬剤が強力な
相乗効果を有していることが示された。その他、
相乗効果が現われる化合物A、Bの濃度の組合わ
せとしては、たとえば第1表の通りである。
The present invention relates to an industrial fungicide characterized by containing 2-mercaptopyridine-N-oxide or a metal salt thereof and 1,2-benzisothiazolin-3-one as active ingredients. The industrial fungicide of the present invention comprising the above two components is
It brings about a stronger synergistic effect of antibacterial action while maintaining the antibacterial spectrum of each component. Almost everything in an aqueous organic system is prone to attack by microorganisms, which can lead to unpleasant odors and suspensions, decomposition of emulsions, coagulation of dispersions, loss of viscosity, and pH changes. This can cause various harmful effects such as changes and the formation of slime, which can greatly reduce the commercial value of the product. For example, circulating cooling type heat exchangers and waste water used in petrochemical factories or chemical factories, etc.
Slime may form in cooling pipes, clogging the pipes and reducing cooling efficiency, or microorganisms generated in white water at paper mills may form muddy slime that peels off and mixes with the paper. The paper may be cut during the process, or spots may appear on the paper.
This can cause unpleasant odors and various other problems. Metal salts of 2-mercaptopyridine-N-oxide, which is one of the active ingredients of the present invention, include alkali metal, alkaline earth metal, and zinc salts, such as sodium, potassium, calcium, magnesium, and zinc salts. These include, but are not limited to. As a result of extensive research into drug combinations that have stronger antibacterial activity than the first component alone and exhibit sustained effects, the present inventors have found that:
It has been found that the combined use of 1,2-benzisothiazolin-3-one as the second component synergistically enhances antibacterial activity and exhibits a connective effect. That is, the present inventors have found that by using these two components together, it can be expected to be effective against most objects to be sterilized, and that the sterilization effect is stronger than that when used alone. The present invention was completed by discovering an industrially significant synergistic effect in which the same effect can be achieved with a fraction of the amount of the drug used. 2-Mercaptopyridine-N-oxide or its metal salt and 1,2-benzisothiazoline-3
-one in a weight ratio of preferably 32:1 to 1:128 (generally particularly preferably 1:1 to 1:4 shows a strong synergistic effect) at a concentration of several ppm. It has become clear that the use of this method can sufficiently inhibit the growth of bacteria. In addition, since the two components exhibit a synergistic effect when used together, it is possible to significantly reduce the amount of drug used, and the cost is reduced accordingly, bringing great practical benefits. In actual use, the components of the present invention are dissolved in a hydrophilic organic solvent (dimethylformamide, ethylene glycol, methylcellosolve, etc.) and a solution (in some cases, a surfactant such as polyoxyethylene alkylamine, alkylolamine, etc.) is added. It is possible to prevent the growth of microorganisms by adding them to the system. Next, the method for testing the synergistic effect of two components used to complete the present invention will be explained. Synergistic Effect Test Method The synergistic effect between two components is measured by the binary dilution method. Both components are diluted to a predetermined concentration, and a fixed amount of each is added to the bouillon medium. Next, inoculate a certain amount of pre-cultured bacterial solution and incubate at 37℃.
After 6.5 hours of shaking culture, the concentration of both components at which no increase in absorbance at 660 nm is observed is defined as the minimum inhibitory concentration (hereinafter referred to as TDMIC) determined by the binary dilution method. Figure 1 is a graph in which the minimum inhibitory concentration (hereinafter referred to as MIC) of each component is placed equally on both axes using standard scale coordinates. In this graph, the area above the curve (i.e., the TDMIC curve) indicates the zone of growth inhibition, and the area below indicates the zone of proliferation. Furthermore, when the diagonal line and the TDMIC curve match, it indicates an additive effect, when the TDMIC curve is above the diagonal line, it indicates an antagonistic effect, and when it is below the diagonal line, it indicates a synergistic effect. Next, the present invention will be explained by examples. In the examples, compound A means the sodium salt of 2-mercaptopyridine-N-oxide, and compound B means 1.2-benzisothiazolin-3-one. Example 1 Synergistic effect against Pseudomonas aeruginosa Compound A and compound B were each administered at 100 μg/
After preparing the sample by diluting it multiple times per ml, the synergistic effect was examined according to the test method described above. The results are shown in FIG. From the figure, this TDMIC curve for Pseudomonas aeruginosa clearly indicates a significant synergistic effect. For example, the synergistic effect of the two components that completely inhibited bacterial growth was demonstrated when the concentration of compound A was 12.5 μg/ml.
It appeared when the concentration of compound B was 3.2 μg/ml. That is, this drug concentration is
It is 1/8 of the MIC of compound B alone, and the MIC of compound B alone.
The amount was approximately 1/16 of that of the drug, indicating that this drug has a strong synergistic effect. others,
Examples of combinations of concentrations of compounds A and B that produce a synergistic effect are shown in Table 1.
【表】
第2図には、第1表に記載されていない組合わ
せの結果も示す。
表中、( )は単独のMICの何分の1かを表わ
す。(以下、表中の( )の意味は同様とする。)
なお、化合物単独のMICは、100μg/mlであ
り、化合物B単独のMICは、50μg/mlである。
実施例 2
バチルス・ズブチリスに対する相乗効果
実施例1と同様に試験した結果を第2表および
第3図に示す。[Table] Figure 2 also shows the results of combinations not listed in Table 1. In the table, () represents a fraction of the individual MIC. (Hereinafter, the meaning of ( ) in the table is the same.) The MIC of compound B alone is 100 μg/ml, and the MIC of compound B alone is 50 μg/ml. Example 2 Synergistic effect on Bacillus subtilis The results of the same test as in Example 1 are shown in Table 2 and Figure 3.
【表】
第3図には、第2表に記載されていない組合わ
せの結果も示す。
なお、化合物A単独のMICは3.2μg/mlであ
り、化合物B単独のMICは3.2μg/mlである。
実施例 3
スタフイロコツカス・アウレウスに対する相乗
効果
実施例1と同様に試験した結果を第3表および
第4図に示す。[Table] Figure 3 also shows the results of combinations not listed in Table 2. Note that the MIC of Compound A alone is 3.2 μg/ml, and the MIC of Compound B alone is 3.2 μg/ml. Example 3 Synergistic effect against Staphylococcus aureus The results of the same test as in Example 1 are shown in Table 3 and FIG. 4.
【表】
第4図には、第3表に記載されていない組合わ
せの結果も示す。
なお、化合物A単独のMICは3.2μg/mlであ
り、化合物B単独のMICは50μg/mlである。
実施例 4
トンネル工事現場で発生する地下水のスライム
による汚染、ひいては排水溝の流れが悪くなり閉
塞にまでおよび、同時に亜臭をはなつ現象が各地
で現われている。その原因菌を含んでいる某トン
ネル内排水溝のスライムを用いて、本発明混合物
の効果を試験した。
先ず、予めブイミン培地にて本スライム形成菌
を前培養する。活性化された液を一定量、滅菌水
に接種する。その後、各種本発明混合物の希釈液
を一定量添加し、37℃にて振盪培養を行う。一定
時間振盪した後、生菌数を平板希釈法にて測定し
た。その結果を第4表に示す。[Table] Figure 4 also shows the results of combinations not listed in Table 3. Note that the MIC of Compound A alone is 3.2 μg/ml, and the MIC of Compound B alone is 50 μg/ml. Example 4 The phenomenon of contamination of underground water by slime generated at tunnel construction sites, which in turn impairs the flow of drainage ditches and even causes blockages, is occurring in various places, and at the same time, a sub-odor is emitted. The effectiveness of the mixture of the present invention was tested using slime from a drain in a certain tunnel that contained the causative bacteria. First, the present slime-forming bacteria are pre-cultured in Buimin medium. Inoculate a certain amount of the activated liquid into sterile water. Thereafter, a certain amount of diluted solutions of various mixtures of the present invention are added, and shaking culture is performed at 37°C. After shaking for a certain period of time, the number of viable bacteria was measured by the plate dilution method. The results are shown in Table 4.
【表】【table】
第1図は、二元希釈法による最小発育阻止濃度
曲線を示すグラフであり、第2,3および4図
は、シユードモナス・エルギノーサ(第2図)、
バチルス・ズブチリス(第3図)およびスタフイ
ロコツカス・アウレウス(第4図)に対する、本
発明の工業用殺菌剤の二元希釈法による最小発育
阻止濃度曲線を示すグラフである。
FIG. 1 is a graph showing the minimum inhibitory concentration curve by the binary dilution method, and FIGS. 2, 3, and 4 are graphs showing Pseudomonas aeruginosa (FIG. 2),
FIG. 4 is a graph showing minimum inhibitory concentration curves of the industrial fungicide of the present invention against Bacillus subtilis (FIG. 3) and Staphylococcus aureus (FIG. 4) by a binary dilution method.
Claims (1)
はその金属塩、および1・2−ベンズイソチアゾ
リン−3−オンを有効成分として含有することを
特徴とする工業用殺菌剤。1. An industrial disinfectant characterized by containing 2-mercaptopyridine-N-oxide or a metal salt thereof and 1,2-benzisothiazolin-3-one as active ingredients.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4354481A JPS57156405A (en) | 1981-03-24 | 1981-03-24 | Fungicide for industrial purpose |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4354481A JPS57156405A (en) | 1981-03-24 | 1981-03-24 | Fungicide for industrial purpose |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57156405A JPS57156405A (en) | 1982-09-27 |
JPS6243966B2 true JPS6243966B2 (en) | 1987-09-17 |
Family
ID=12666680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4354481A Granted JPS57156405A (en) | 1981-03-24 | 1981-03-24 | Fungicide for industrial purpose |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57156405A (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9813271D0 (en) | 1998-06-19 | 1998-08-19 | Zeneca Ltd | Composition and use |
JP2000191412A (en) * | 1998-12-28 | 2000-07-11 | Nagase Kasei Kogyo Kk | Microbicidal composition |
GB0012786D0 (en) | 2000-05-26 | 2000-07-19 | Avecia Ltd | Method and compositions |
US7468384B2 (en) | 2004-11-16 | 2008-12-23 | Rohm And Haas Company | Microbicidal composition |
US9723842B2 (en) | 2006-05-26 | 2017-08-08 | Arch Chemicals, Inc. | Isothiazolinone biocides enhanced by zinc ions |
DE102006045066B4 (en) | 2006-09-21 | 2010-07-01 | Schülke & Mayr GmbH | Microbicidal preparation based on 1,2-benzisothiazolin-3-one with an aromatic alcohol content |
JP2008247751A (en) * | 2007-03-29 | 2008-10-16 | Aquas Corp | Granular green alga controller and method for controlling granular green alga |
US8317912B2 (en) * | 2011-03-28 | 2012-11-27 | Arch Chemicals, Inc. | Wet state preservation of mineral slurries |
JP6510383B2 (en) * | 2015-10-26 | 2019-05-08 | 水ing株式会社 | Cooling water treatment chemical and cooling water treatment method |
EP3493679A4 (en) * | 2016-09-09 | 2020-04-29 | Lonza Inc. | Enhanced biocide composition containing an isothiazolinone and a pyrithione |
-
1981
- 1981-03-24 JP JP4354481A patent/JPS57156405A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57156405A (en) | 1982-09-27 |
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