JPH0881445A - Novel alkyl benzimidazole-2-carbamate ester compound and itsproduction - Google Patents
Novel alkyl benzimidazole-2-carbamate ester compound and itsproductionInfo
- Publication number
- JPH0881445A JPH0881445A JP7216847A JP21684795A JPH0881445A JP H0881445 A JPH0881445 A JP H0881445A JP 7216847 A JP7216847 A JP 7216847A JP 21684795 A JP21684795 A JP 21684795A JP H0881445 A JPH0881445 A JP H0881445A
- Authority
- JP
- Japan
- Prior art keywords
- benzimidazole
- long
- chain alkyl
- catalyst
- represented
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】Detailed Description of the Invention
【０００１】[0001]
【発明の属する技術分野】本発明はプラスチック用途に
適合した新規の化合物とその製造方法及びその抗菌剤と
しての用途に関する。さらに詳しくは、次の構造式(I)
で表わされる長鎖アルキル基で置換されたベンゾイミダ
ゾール−２−カルバミン酸アルキルエステルに関するも
のである。但し、下記式中、ＲはＣ10-24 の長鎖アルキ
ル基を示す。TECHNICAL FIELD The present invention relates to a novel compound suitable for plastic use, a method for producing the same, and use thereof as an antibacterial agent. More specifically, the following structural formula (I)
The present invention relates to a benzimidazole-2-carbamic acid alkyl ester substituted with a long chain alkyl group. However, in the following formula, R represents a C 10-24 long-chain alkyl group.
【０００２】[0002]
【化５】 [Chemical 5]
【０００３】[0003]
【従来の技術】前記式(I) において、Ｒがメチル基であ
る化合物は、次の構造式(II)で表わされるベンゾイミダ
ゾール−２−カルバミン酸メチルエステルであり、一般
名がカルベンダジム（以下、ＣＢＺと表示する）として
広く知られている化合物である。この化合物は、米国特
許第３，０１０，９６８号等に毒性が非常に低い抗菌剤
（ＬＤ50＝６，８００ｍｇ／ｋｇ，ねずみ）として記載
されており、塗料、電気機器及びプラスチック用途にも
広く使用されている。In the above formula (I), the compound in which R is a methyl group is benzimidazole-2-carbamic acid methyl ester represented by the following structural formula (II), and its general name is carbendazim (hereinafter referred to as carbendazim). , CBZ)). This compound is described in US Pat. No. 3,010,968 as an antibacterial agent having extremely low toxicity (LD 50 = 6,800 mg / kg, mouse), and is widely used for paints, electric devices and plastics. in use.
【０００４】[0004]
【化６】 [Chemical 6]
【０００５】[0005]
【発明が解決しようとする課題】しかしながら、ＣＢＺ
のような有機抗菌剤をポリエチレン又はポリプロピレン
のようなプラスチックに添加して使用する場合、抗菌剤
が溶出してプラスチックの抗菌力が急激に低下するとい
う問題がある。このような現象は有機抗菌剤とプラスチ
ックとの相溶性が低いことに起因すると予想される。[Problems to be Solved by the Invention] However, CBZ
When such an organic antibacterial agent is used by being added to a plastic such as polyethylene or polypropylene, there is a problem that the antibacterial agent is eluted and the antibacterial activity of the plastic is sharply reduced. Such a phenomenon is expected to be due to the low compatibility between the organic antibacterial agent and the plastic.
【０００６】そこで、本発明者らは前記のような課題を
解決するために研究した。その結果、プラスチックとの
相溶性が向上した親油性の新規の化合物(I) を開発し、
このような新規の化合物(I) が抗菌剤として有用である
ことを見い出して本発明に至った。Therefore, the present inventors have conducted research to solve the above problems. As a result, we developed a new lipophilic compound (I) with improved compatibility with plastics,
The present invention was completed by finding that such a novel compound (I) is useful as an antibacterial agent.
【０００７】本発明の目的は、下記構造式(I) で表わさ
れる長鎖アルキル基で置換されたベンゾイミダゾール−
２−カルバミン酸アルキルエステルを提供することにあ
る。An object of the present invention is to provide a benzimidazole group substituted with a long chain alkyl group represented by the following structural formula (I).
To provide an alkyl 2-carbamic acid ester.
【０００８】[0008]
【化７】 [Chemical 7]
【０００９】ここで、ＲはＣ10-24 の長鎖アルキル基を
示す。又、本発明の他の目的は、前記構造式(I) で表わ
される長鎖アルキル基で置換されたベンゾイミダゾール
−２−カルバミン酸アルキルエステルを製造する方法を
提供することにある。又、本発明のさらに他の目的は、
前記構造式(I) で表わされる長鎖アルキル基で置換され
たベンゾイミダゾール−２−カルバミン酸アルキルエス
テルからなる抗菌剤を提供することにある。Here, R represents a C 10-24 long-chain alkyl group. Another object of the present invention is to provide a method for producing a benzimidazole-2-carbamic acid alkyl ester substituted with a long chain alkyl group represented by the structural formula (I). Still another object of the present invention is to
Another object of the present invention is to provide an antibacterial agent comprising a benzimidazole-2-carbamic acid alkyl ester substituted with a long chain alkyl group represented by the structural formula (I).
【００１０】[0010]
【課題を解決するための手段】本発明の新規の化合物
(I) は従来のＣＢＺとして知られたベンゾイミダゾール
−２−カルバミン酸メチルエステルにおいて、メチル置
換基を長鎖アルキル基で置換して親油性を高めることに
より、プラスチックとの相溶性を増大させたものであ
る。本発明による前記化合物(I) は、下記構造式(II)で
表わされるカルベンダジム（ＣＢＺ）と炭素原子数１０
〜２４のアルコールを、触媒の存在下で６０℃以上の温
度で加熱させることにより製造される。The novel compounds of the present invention
(I) is a conventional benzimidazole-2-carbamic acid methyl ester known as CBZ, in which the methyl substituent is substituted with a long-chain alkyl group to increase lipophilicity, thereby increasing compatibility with plastics. It is a thing. The compound (I) according to the present invention comprises carbendazim (CBZ) represented by the following structural formula (II) and 10 carbon atoms.
-24 alcohols are prepared by heating in the presence of a catalyst at temperatures above 60 ° C.
【００１１】[0011]
【化８】 Embedded image
【００１２】前記反応において、ジメチルスルホキシ
ド、ジメチルホルムアミドのような溶媒を使用するか又
は使用せずに反応させ、添加されたアルコールとＣＢＺ
のトランスエステル化反応（Transesterification)によ
り添加アルコールの炭素原子数に相応するベンゾイミダ
ゾール−２−カルバミン酸アルキルエステルが得られ
る。この際、添加されるアルコールの量は、１．０〜１
０当量とすることが望ましい。In the above reaction, the reaction is carried out with or without a solvent such as dimethyl sulfoxide or dimethylformamide, and the added alcohol and CBZ are reacted.
The transesterification reaction of (1) gives benzimidazole-2-carbamic acid alkyl ester corresponding to the number of carbon atoms of the added alcohol. At this time, the amount of alcohol added is 1.0 to 1
It is desirable to make it 0 equivalent.
【００１３】又、前記反応はアルミニウムイソプロポキ
シドのような触媒の存在下で行われる。そして、副生成
物であるメタノールを易しく除去し得るように、メタノ
ールの沸点以上で反応を遂行することが望ましく、特に
６０〜１５０℃の範囲が望ましい。The above reaction is also carried out in the presence of a catalyst such as aluminum isopropoxide. Then, in order to easily remove the by-product methanol, it is desirable to carry out the reaction at the boiling point of methanol or higher, particularly in the range of 60 to 150 ° C.
【００１４】[0014]
【実施例】以下、本発明を次の実施例に従ってより具体
的に説明するが、本発明は下記の実施例に限定されるも
のではない。次の実施例１は前記構造式中のＲがＣ16で
ある化合物（以下ＨＣＢＺと表示する）の製造方法を記
述したものである。実施例２〜４は前記ＨＣＢＺの特性
テスト方法を記述したものである。具体的に実施例２は
プラスチックとのコンパウンディングにより試片を製作
する方法を、実施例３はプラスチック試片の抗菌力測定
方法及びその結果を、実施例４はプラスチック試片の抗
菌力持続性テスト方法及びその結果を記述したものであ
る。EXAMPLES The present invention will now be described more specifically according to the following examples, but the present invention is not limited to the following examples. The following Example 1 describes a method for producing a compound in which R in the above structural formula is C 16 (hereinafter referred to as HCBZ). Examples 2 to 4 describe the HCBZ characteristic test method. Specifically, Example 2 is a method for producing a test piece by compounding with a plastic, Example 3 is a method for measuring the antibacterial activity of a plastic sample and the results thereof, and Example 4 is a sustainability of the antibacterial activity of a plastic sample. It describes the test method and its results.
【００１５】実施例１：ベンゾイミダゾール−２−カル
バミン酸ヘキサデシルエステル（ＨＣＢＺ）の製造 磁気攪拌装置と首の短い蒸留装置（Short Path Distill
ation Set)とを備えた５００ｍｌの丸いフラスコに、Ｃ
ＢＺ（９．０ｇ，５０ｍｍｏｌ）、１−ヘキサデカノー
ル（３０ｇ）及びアルミニウムイソプロポキシド（１０
０ｍｇ）を添加し、油浴で９０℃に加熱し１８時間攪拌
し続ける。この際、レシーバーフラスコに副生成物であ
るメタノールが蒸留されて集まり、薄膜クロマトグラフ
ィーで反応の進捗度を確認する。反応物は冷えながら固
体化するので、約５５℃前後で１リットルのヘキサンを
添加し１時間攪拌した後、濾過して生成物を得る。真空
乾燥後に１７．５ｇのＨＣＢＺを得る（収率８８％）。
このような方法により得られた主生成物をＨ−ＮＭＲで
分析した結果、生成物中には未反応ＣＢＺ又は１−ヘキ
サデカノールが残っていないことが確認された。 ＨＣＢＺの物理的性質： ｍｐ＝３２０℃以上（decomp) Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６，２００ＭＨＺ）８０℃で
ｐｐｍ０．８５（３Ｈ，ｔ）、１．２８（２６Ｈ，
Ｓ）、１．６２（２Ｈ，ｔ）、４．１７（２Ｈ，ｔ）、
７．０８（２Ｈ，ｍ）、７．３９（２Ｈ，ｍ）、１１．
５８（１Ｈ，broad) Example 1: Benzimidazole-2-cal
Manufacture of hexadecyl humic acid ester (HCBZ) Magnetic stirrer and short neck distillation unit (Short Path Distill
ation set) and a 500 ml round flask with
BZ (9.0 g, 50 mmol), 1-hexadecanol (30 g) and aluminum isopropoxide (10
0 mg), heat to 90 ° C. in an oil bath and continue stirring for 18 hours. At this time, by-product methanol was distilled and collected in the receiver flask, and the progress of the reaction was confirmed by thin-layer chromatography. Since the reaction product solidifies while cooling, 1 liter of hexane is added at about 55 ° C., the mixture is stirred for 1 hour, and then filtered to obtain a product. After vacuum drying, 17.5 g of HCBZ is obtained (yield 88%).
As a result of H-NMR analysis of the main product obtained by such a method, it was confirmed that unreacted CBZ or 1-hexadecanol did not remain in the product. Physical properties of HCBZ: mp = 320 ° C. or higher (decomp) H-NMR (DMSO-d6, 200 MHZ) ppm at 80 ° C. 0.85 (3H, t), 1.28 (26H, 26H,
S), 1.62 (2H, t), 4.17 (2H, t),
7.08 (2H, m), 7.39 (2H, m), 11.
58 (1H, broad)
【００１６】実施例２：プラスチック試片製作 有機及び無機抗菌剤と基本樹脂としてＨＤＰＥ（油公の
ＢＤ８００ grade) とのコンパウンディング例を記述し
たものである。抗菌剤濃度１％の試片を製造するため、
有機抗菌剤の場合にはＣＢＺ又は実施例１によるＨＣＢ
Ｚそれぞれ１ｇずつと基本樹脂９９ｇを乾式混合した
後、ブラベンダープラスティコーダー（Brabender Plas
ticoder)のバンバリミキサーを使用して３分間ブレンデ
ィング（５０ｒｐｍ，１６０℃）した。無機抗菌剤の場
合には、ＣＣＩＣ社のＡＩＳ抗菌剤を１７％含有したマ
スターバッチ６ｇに９４ｇの基本樹脂を前記と同方法で
ブレンディングした。このように得られた抗菌剤濃度１
％のプラスチックコンパウンドを圧縮成形（１９０℃で
予備加熱５分、硬化５分、冷却１分）して厚さ１ｍｍの
プラスチック試片を製造し、次の実施例３〜４により抗
菌性及びその持続性をテストした。 Example 2 Production of Plastic Specimen A compounding example of organic and inorganic antibacterial agents and HDPE (BD800 grade of Yukiko) as a basic resin is described. In order to manufacture a specimen with an antibacterial agent concentration of 1%,
In the case of an organic antibacterial agent, CBZ or HCB according to Example 1
After dry-mixing 1 g each of Z and 99 g of the base resin, Brabender Plascoder (Brabender Plas
It was blended (50 rpm, 160 ° C.) for 3 minutes using a Banbury mixer of ticoder). In the case of an inorganic antibacterial agent, 94 g of the basic resin was blended in the same manner as described above to 6 g of a masterbatch containing 17% of AIC antibacterial agent manufactured by CCIC. Antimicrobial concentration 1 thus obtained
% Plastic compound by compression molding (preheating at 190 ° C. for 5 minutes, curing for 5 minutes, cooling for 1 minute) to produce a plastic specimen with a thickness of 1 mm. Tested for sex.
【００１７】実施例３：ＨＣＢＺを含有したプラスチッ
ク試片の抗菌力測定 黴の成長が良い“芋澱粉−デキストロース培地”で作っ
た寒天培地（５ｍｌ）と“アスペルジラスナイザー”及
び５種の黴胞子溶液（１ｍｌ）を良く混合した後、４５
℃に維持しながら固くならないようにする。２０×３０
ｍｍの大きさに切ったプラスチック試片をエタノールで
滅菌して平板培地上に置き、前記準備した寒天培地を薄
くまき散らしながら固める。３０℃で５〜７日間培養し
ながら黴の成長を観察する。標準対照試片での黴の成長
度と比較して黴の成長程度を数値で表示する（表１）。
このような方法によりそれぞれＨＣＢＺ、ＣＢＺ、無機
抗菌剤ＡＩＳが１％含まれたプラスチック試片の抗菌力
を測定した。その結果、ＨＣＢＺの抗菌力がＣＢＺ及び
ＡＩＳより優秀であった（表２）。 Example 3: HCBZ-containing plastic
Measurement of antibacterial activity of test pieces Agar medium (5 ml) made of "potato starch-dextrose medium" with good mold growth, "Aspergillus nizer" and 5 types of mold spore solution (1 ml) were mixed well, and then 45
Keep it at ℃ so that it does not become hard. 20 x 30
A plastic test piece cut into a size of mm is sterilized with ethanol and placed on a plate medium, and the prepared agar medium is thinly scattered and solidified. The growth of mold is observed while culturing at 30 ° C. for 5 to 7 days. The degree of mold growth is indicated numerically in comparison with the degree of mold growth in the standard control sample (Table 1).
By such a method, the antibacterial activity of each of the plastic specimens containing HCBZ, CBZ and 1% of the inorganic antibacterial agent AIS was measured. As a result, the antibacterial activity of HCBZ was superior to that of CBZ and AIS (Table 2).
【００１８】[0018]
【表１】 [Table 1]
【００１９】[0019]
【表２】 [Table 2]
【００２０】実施例４：プラスチック試片の抗菌力持続
性テスト 抗菌剤を入れなかった基本樹脂試片を始めとし、次の表
３の４種の試片を循環水の温度が５０℃に維持される恒
温水槽内に入れ、溶出された抗菌剤による影響を除去す
るために１日１回程度循環水を交替した。一定期間が経
過した後、試片を恒温水槽から取り出して実施例３と同
じ方法で抗菌力を測定した。４週間経過後に採取した試
片の黴に対する抗菌力と実験開始当時の試片の抗菌力と
を比較した結果を次の表３に示した。 Example 4: Sustaining antibacterial activity of plastic samples
The basic resin test piece without the antibacterial agent was put in the constant temperature water bath where the temperature of the circulating water was maintained at 50 ° C. The circulating water was replaced about once a day to eliminate the effect. After a certain period of time passed, the test piece was taken out from the constant temperature water bath and the antibacterial activity was measured by the same method as in Example 3. The following Table 3 shows the results of comparison between the antibacterial activity against mold of the test pieces collected after 4 weeks and the antibacterial activity of the test pieces at the start of the experiment.
【００２１】[0021]
【表３】 [Table 3]
【００２２】前記表３の結果から分かるように、本発明
によるＨＣＢＺが含有されたプラスチック試片が従来の
ＣＢＺを含有した試片に比べ、抗菌力の持続性が数等向
上された。As can be seen from the results shown in Table 3, the antibacterial activity of the HCBZ-containing plastic test piece of the present invention was improved several times as compared with the conventional CBZ-containing test piece.
【００２３】[0023]
【発明の効果】以上説明したように、このような本発明
の製造方法により得られた化合物をプラスチックに添加
して製造した試片はＣＢＺを添加した試片及び無機系抗
菌剤を添加した常用製品（日本国、触媒化成工業）より
抗菌力が優秀であり、長期間持続される効果があること
が確認された。As described above, the test piece manufactured by adding the compound obtained by the manufacturing method of the present invention to the plastic is a CBZ-added test piece or an inorganic antibacterial agent. It was confirmed that the product has superior antibacterial activity than that of the product (Catalyst Kasei Co., Ltd.) and has a long-lasting effect.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 チュン ダェウォン 大韓民国、ダエジェゥン、ユスング、ジン スンドン、ダエリン・デュレ・アパート 106−105 (72)発明者 バン サング 大韓民国、ダエジェゥン、スーグ、ウェル ピュンドン、ダモア・アパート 101− 1409 (72)発明者 チョン ジャェウー 大韓民国、ダエジェゥン、ダェドクグ、ジ ュンミンドン 243−40 (72)発明者 ハーン ジョンソク 大韓民国、キュンギド、スウォン、ジャン ガング、ソンジュクドン、ドンジン・アパ ート ２−205 (72)発明者 リム クァンミン 大韓民国、ダエジェゥン、ユスング、ジュ ンミンドン、セジョン・アパート 109− 504 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Chun Daewon South Korea, Daejeung, Yusung, Jin Sung Dong, Daerin Dure Apartment 106-105 (72) Inventor Bansang Republic of Korea, Daejeong, Sugu, Wel Phun Dong, Damoa Apartment 101-1409 (72) Inventor Chung Jae Woo South Korea, Daejeung, Daed Cuk, Jung Min Dong 243-40 (72) Inventor Hahn Jong Suk Republic of Korea, Kyun Gide, Suwon, Jiang Gang, Song Juk Dong, Dong Jin Apat 2-205 (72) Inventor Lim Kwang Min South Korea, Daejeung, Yusung, Jun Min Dong, Sejong Apartment 109-504
Claims (6)
の長鎖アルキル基を示す。］で表わされるベンゾイミダ
ゾール−２−カルバミン酸アルキルエステル。 【化１】 1. A compound represented by the following general formula (I) [wherein R is C 10-24:
The long-chain alkyl group of ] The benzimidazole-2-carbamic acid alkyl ester represented by these. Embedded image
ダジムと炭素原子数１４〜２４のアルコールを触媒存在
下で６０℃以上の温度に加熱して製造することを特徴と
する下記の構造式(I) ［但し、ＲはＣ10-24 の長鎖アル
キル基を示す。］で表わされるベンゾイミダゾール−２
−カルバミン酸アルキルエステルの製造方法。 【化２】 【化３】 2. The following structure characterized by being produced by heating carbendazim represented by the following structural formula (II) and an alcohol having 14 to 24 carbon atoms to a temperature of 60 ° C. or higher in the presence of a catalyst. Formula (I) [wherein R represents a C 10-24 long-chain alkyl group. ] Benzimidazole-2 represented by
-Method for producing carbamic acid alkyl ester. Embedded image [Chemical 3]
あることを特徴とする請求項２記載の方法。3. The method according to claim 2, wherein the catalyst is aluminum isopropoxide.
ることを特徴とする請求項２又は３記載の方法。4. The method according to claim 2 or 3, wherein the amount of alcohol is 1.0 to 10 equivalents.
されることを特徴とする請求項２〜４のいずれか１項に
記載の方法。5. The method according to any one of claims 2 to 4, wherein the reaction temperature is maintained in the range of 60 to 150 ° C.
の長鎖アルキル基を示す。］で表わされるベンゾイミダ
ゾール−２−カルバミン酸アルキルエステルからなる抗
菌剤。 【化４】 6. The following general formula (I) [wherein R is C 10-24
The long-chain alkyl group of ] The antibacterial agent which consists of benzimidazole-2-carbamic acid alkyl ester represented by these. [Chemical 4]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR94-21450 | 1994-08-29 | ||
| KR1019940021450A KR100314828B1 (en) | 1994-08-29 | 1994-08-29 | Benzimidazol-2-carbamate alkylester and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0881445A true JPH0881445A (en) | 1996-03-26 |
Family
ID=19391411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7216847A Pending JPH0881445A (en) | 1994-08-29 | 1995-08-25 | Novel alkyl benzimidazole-2-carbamate ester compound and itsproduction |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH0881445A (en) |
| KR (1) | KR100314828B1 (en) |
| CN (1) | CN1122332A (en) |
| TW (1) | TW293023B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004043473A (en) * | 2002-07-03 | 2004-02-12 | Samsung Electronics Co Ltd | Antibacterial additive and ink composition containing the same |
| KR100484154B1 (en) * | 2002-08-28 | 2005-04-19 | 삼성전자주식회사 | Antibiotic colorant and ink composition comprising the same |
| EP1671958A1 (en) * | 2004-09-27 | 2006-06-21 | Fuji Photo Film Co., Ltd. | Method of producing amide compound |
| KR100773576B1 (en) * | 2001-11-14 | 2007-11-05 | 에스케이케미칼주식회사 | Preservative having improved fungicidal and algicidal effect |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100346251B1 (en) * | 2000-05-13 | 2002-08-01 | 정대원 | Water-soluble carbendazim derivatives and process for preparing same |
| CN104530008B (en) * | 2014-12-18 | 2016-08-24 | 浙江工业大学 | A kind of benzimidazoles compound containing 1,2,3-triazole and application thereof |
| CN104496975B (en) * | 2014-12-18 | 2017-01-11 | 浙江工业大学 | Benzimidazole compound containing isoxazole and application of compound |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2227919C2 (en) * | 1972-06-08 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | Process for the preparation of benzimidazol-2-yl-carbamic acid methyl ester |
| IL43396A (en) * | 1972-10-14 | 1976-07-30 | Hoechst Ag | Process for the preparation of 2-benzimidazole-carbamic acid alkyl and benzyl esters |
| JPS5857367A (en) * | 1981-09-30 | 1983-04-05 | Shinto Paint Co Ltd | Industrial antifungal composition |
-
1994
- 1994-08-29 KR KR1019940021450A patent/KR100314828B1/en not_active IP Right Cessation
-
1995
- 1995-08-14 TW TW084108466A patent/TW293023B/zh not_active IP Right Cessation
- 1995-08-25 JP JP7216847A patent/JPH0881445A/en active Pending
- 1995-08-29 CN CN95109524A patent/CN1122332A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100773576B1 (en) * | 2001-11-14 | 2007-11-05 | 에스케이케미칼주식회사 | Preservative having improved fungicidal and algicidal effect |
| JP2004043473A (en) * | 2002-07-03 | 2004-02-12 | Samsung Electronics Co Ltd | Antibacterial additive and ink composition containing the same |
| KR100484154B1 (en) * | 2002-08-28 | 2005-04-19 | 삼성전자주식회사 | Antibiotic colorant and ink composition comprising the same |
| EP1671958A1 (en) * | 2004-09-27 | 2006-06-21 | Fuji Photo Film Co., Ltd. | Method of producing amide compound |
| US7541459B2 (en) | 2004-09-27 | 2009-06-02 | Fujifilm Corporation | Method of producing amide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| KR960007569A (en) | 1996-03-22 |
| KR100314828B1 (en) | 2002-02-19 |
| CN1122332A (en) | 1996-05-15 |
| TW293023B (en) | 1996-12-11 |
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