JPS6084203A - Antimicrobial agent - Google Patents

Antimicrobial agent

Info

Publication number
JPS6084203A
JPS6084203A JP19360383A JP19360383A JPS6084203A JP S6084203 A JPS6084203 A JP S6084203A JP 19360383 A JP19360383 A JP 19360383A JP 19360383 A JP19360383 A JP 19360383A JP S6084203 A JPS6084203 A JP S6084203A
Authority
JP
Japan
Prior art keywords
diol
bromo
based compound
bromonitroalcohol
compound
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
Application number
JP19360383A
Other languages
Japanese (ja)
Inventor
Kingo Chu
忠 錦吾
Fujiaki Mochizuki
望月 富士秋
Yoshiko Yasunaga
安永 佳子
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kurita Water Industries Ltd
Original Assignee
Kurita Water Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kurita Water Industries Ltd filed Critical Kurita Water Industries Ltd
Priority to JP19360383A priority Critical patent/JPS6084203A/en
Publication of JPS6084203A publication Critical patent/JPS6084203A/en
Pending legal-status Critical Current

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

PURPOSE:An antimicrobial agent, containing an isothiazolone based compound and a bromonitroalcohol based compound together, and capable of preventing sufficiently slime trouble in water systems, e.g. cooling water, paper and pulp water systems. CONSTITUTION:An antimicrobial agent containing an isothiazolone based compound of formula I (X is halogen; Y is H or X and Y form benzene ring; R is alkyl) such as 5-chloro-2-methyl-4-isothiazolin-3-one or 1,2-benzisothiazolin-3-one and a bromonitroalcohol based compound of formula II (R and R' are 1-5C alkyl) such as 2-bromo-2-nitropropane-1,3-diol,3-bromo-2-nitropropane-1,3-diol or 3-bromo-3-nitropenten-2,4-diol, preferably at (4:1)-(1:1) ratio in combination.

Description

【発明の詳細な説明】 本発明は用水系の抗菌剤に関する。[Detailed description of the invention] The present invention relates to a water-based antibacterial agent.

冷却水系においては、ズーグレア状細菌、藻類、糸状菌
等によるスライム障害が引き起こされる場合が多い。そ
の結果、熱効率の低下や通水の悪化をもたらすばかシで
なく、機器、配管等の局部腐食発生の原因ともなってい
る。また、紙・パルプ・水系においては、細菌、糸状菌
、酵母類によるスライム障害が主に抄紙工程で引き起こ
される。スライムはパイプスラリーの異物として混入す
ると、製品の品質全低下させるばかりでなく、紙切れを
生じ抄紙機の連続運転を阻害する要因となシ生産効率を
大幅に低下さ謙ト ス、− こうしたスライム障害全防止するには、上記のようなス
ライムl[菌t@壊又は成長阻害する必要がある。この
ため従来よp抗菌剤として、インチアゾロン系化合物あ
るいはブロモニトロアルコール系化合物が別々に提案さ
れている。
In cooling water systems, slime damage is often caused by zooglai bacteria, algae, filamentous fungi, etc. As a result, this not only causes a decrease in thermal efficiency and worsens water flow, but also causes local corrosion of equipment, piping, etc. In addition, in paper/pulp/water systems, slime damage caused by bacteria, filamentous fungi, and yeast is mainly caused during the paper-making process. When slime is mixed in as a foreign substance in pipe slurry, it not only reduces the overall quality of the product, but also causes paper breakage and disturbs the continuous operation of the paper machine, greatly reducing production efficiency. To completely prevent slime bacteria as described above, it is necessary to destroy or inhibit their growth. For this reason, inthiazolone compounds or bromonitroalcohol compounds have been proposed separately as p-antibacterial agents.

しかしながら、これらの抗菌剤によっては必ずしもスラ
イム障害全十分に防止することはできなかった。特にイ
ンチアゾロン系化合物は、長期的に使用するとスライム
構成菌に耐性がつきやすく、抵抗性のある細菌が優先し
やすいということが知られている。更に、近年は処理コ
スト低下の意味で、よシ効力の高い抗菌剤か要求されて
いる。
However, these antibacterial agents were not always able to completely prevent slime damage. In particular, it is known that when intiazolone compounds are used over a long period of time, slime-constituting bacteria tend to develop resistance, and resistant bacteria tend to take priority. Furthermore, in recent years, there has been a demand for highly effective antibacterial agents in order to reduce processing costs.

本発明の目的は、冷却水系、紙・パルプ水系等の用水系
におけるスライム障害を十分に防止できるだけの高い効
力を有する抗菌剤全提供する所にある。
An object of the present invention is to provide an antibacterial agent that is highly effective enough to sufficiently prevent slime damage in water systems such as cooling water systems and paper/pulp water systems.

本発明者らは、各々単独で使用さtてい友上記抗菌剤の
併用によって格段に優れた効力が発) 揮されることを見い出した。即ち、本発明はイソテアゾ
ロン系化合物とブロモニトロアルコール系化合物とを含
む抗菌剤である。
The present inventors have discovered that the above antibacterial agents are more effective when used in combination than when used alone. That is, the present invention is an antibacterial agent containing an isoteazolone compound and a bromonitroalcohol compound.

インチアゾロン系化合物は、一般式 (XはH又はハロゲン原子を示し、YはHt示し、Xと
Yでベンゼン14に表わすこともできる。Ri’l:炭
素数1〜5のアルキル基を示す。) で表わすことができる化合物である。この代表例として
は、5−クロロ−2−メチル−4−インチアブリン−3
−オン、112−””ンダインチアゾリンー3−オンが
挙げらnる。
The intiazolone compound has the general formula (X represents H or a halogen atom, Y represents Ht, and X and Y can also be represented as benzene 14. Ri'l: represents an alkyl group having 1 to 5 carbon atoms.) It is a compound that can be expressed as A typical example of this is 5-chloro-2-methyl-4-inthiabulin-3
-one, 112-one, 112-one, dithiazolin-3-one, etc.

ブロモニトロアルコール系化合物は、一般式%式% (R及びR′は炭素数1〜5のアルキル基金示す。) で表わすことができる化合物である。この代表例トシて
は、2−ブロモ−2−二トロプロパンー1.3−ジオー
ル、3〜ゾロモー3−ニトロペンテン−2,4−ジオー
ルが挙ケラれる。
The bromonitroalcohol compound is a compound that can be represented by the general formula % (R and R' represent an alkyl group having 1 to 5 carbon atoms). Representative examples include 2-bromo-2-nitropropane-1,3-diol and 3-zolomo-3-nitropentene-2,4-diol.

インチアゾロン系化合物とブロモニトロアルコール系化
合物との混合比は、特に限定されないが、4:1〜l:
lの範囲の場合に特に高い効力を発揮する。また本発明
の使用法は、従来と同様に用水系に添加すれば良く、両
者は予め所定濃度まぜ合わせても別々に系に添加しても
良い。添加濃度は用水系等によっても異なるが、通常0
.5〜500〜/l程度であれは良い。
The mixing ratio of the intiazolone compound and the bromonitroalcohol compound is not particularly limited, but is 4:1 to 1:1:
Particularly high efficacy is exhibited in the range of l. Further, in the method of use of the present invention, it is sufficient to add them to the water system in the same manner as in the past, and both may be mixed in advance at a predetermined concentration or may be added to the system separately. The concentration added varies depending on the water system, etc., but is usually 0.
.. It is good if it is about 5-500-/l.

本発明によれば、インチアゾロン系化合物とブロモニト
ロアルコール系化合物全併用することによp1従来知ら
れていなかったような優れた相乗効果が得られる。即ち
、スライムコントロール効果が単独使用時よジも向上し
、抗菌スペクトルが単独使用時よりも広くな9、また耐
性がつきにくくなってよジ長期的な使用が可能となる。
According to the present invention, an excellent synergistic effect, which has not been known in the past, can be obtained by using an intiazolone compound and a bromonitroalcohol compound in combination. That is, the slime control effect is improved when used alone, the antibacterial spectrum is broader than when used alone9, and resistance is less likely to develop, allowing long-term use.

なお、開化合物の併用によって不安定となったり化学的
な反応を起こすこともない。
In addition, when an open compound is used in combination, it does not become unstable or cause a chemical reaction.

また人体に対する毒性が高くなることもない。Moreover, the toxicity to the human body does not become high.

実施例1 大腸菌を用いて最小増殖阻止濃度(MIC24)葡求め
た結果を図に示した。試験条件は、pn 7のペプトン
−酵母エキス金ベースとする液体培地(ペプトン1 g
/II 、酵母エキス19711を含む)に1.0’ 
f@/rnlとなるように接種し、24時間、35Cで
振盪培養した。ここで用いたインチアゾロン系化合物は
、5−クロロ−2−メチル−4−インチアゾリン−3−
オン(A)で純分10%テオル。ブロモニトロアルアル
コールM化合物上、2−7”ロモー2−ニトロプロノξ
ンー1.3−ジオール■)で純分98%である。結果は
2回の平均値で示した。
Example 1 The results of determining the minimum growth inhibitory concentration (MIC24) using Escherichia coli are shown in the figure. The test conditions were peptone-yeast extract gold-based liquid medium of pn 7 (peptone 1 g
/II, containing yeast extract 19711) to 1.0'
The cells were inoculated at f@/rnl and cultured with shaking at 35C for 24 hours. The inthazolone compound used here was 5-chloro-2-methyl-4-inthiazoline-3-
On (A) is 10% pure theol. On bromonitroalcohol M compound, 2-7” bromo 2-nitroprono
-1,3-diol ■) with a purity of 98%. The results are shown as the average value of two measurements.

図に示した結果から、A:Bが4:1〜1:1の範囲で
特に高い相乗効果を示していることが判る。
From the results shown in the figure, it can be seen that a particularly high synergistic effect is exhibited when A:B is in the range of 4:1 to 1:1.

実施例2 次m11/7″IMr−θ)刊)岳二φ、ム4離l奇1
址の蔵fついて、純分10%の1,2−ベンゾイソチア
ゾリン−3−オン(C)と純分98%の3−ブロモ−3
−ニトロペンテン−2,4−ジオール(D)全、各々単
独使用の場合と、CとDi併用した場合の抗菌力全比較
した結果を表−1に示した。試験条件は実施例1と同じ
である。表−1に示しだ結果よシ抗菌スペクトルが広く
なったことが判る。
Example 2 Next m11/7″IMr-θ) Published) Take 2 φ, Mu 4 Release 1
At the warehouse, 1,2-benzisothiazolin-3-one (C) with a purity of 10% and 3-bromo-3 with a purity of 98%.
-Nitropentene-2,4-diol (D) The results of a complete comparison of the antibacterial activity when each was used alone and when C and Di were used in combination are shown in Table 1. The test conditions are the same as in Example 1. The results shown in Table 1 show that the antibacterial spectrum was broadened.

表−1 a:板紙抄紙系よりの分離菌 b=ダンボール故紙系よりの分隙1′菌c:トイレット
ペーパー抄紙糸よシの分離菌実施例3 5−クロロ−2−メチル−4−インテアゾリン−3−オ
ン(4)と2−ブロモ−2−二トロプロパン−1,3−
ジオール(B)と全1:1の割合で り混合したものを
、ブロー水燻当υ5m9/lとなるようにモデル冷却水
ゾラントで1力月間連続添加した。その結果ケ表−2に
示した。また試験 ・開始直後の循環水中の生育菌に対
するMICと試験終了後の循環水中の生育菌に対するM
IC全測定した結果についても示した。比較のためAと
Bを各々単独で試験した場合についても示した。表−2
に示した結果よジ、スライムコントロール効果が上昇す
るとともに、耐性がつきにくく、より長期的な使用が可
能であることが理解される。
Table 1 a: Bacteria isolated from paperboard making system b = Gap 1' from cardboard waste paper system c: Bacteria isolated from toilet paper making yarn Example 3 5-chloro-2-methyl-4-inteazoline- 3-one (4) and 2-bromo-2-nitropropane-1,3-
A mixture of diol (B) and diol (B) in a total ratio of 1:1 was continuously added for one month using model cooling water Zorant so that the amount of blow water was 5 m9/l. The results are shown in Table 2. In addition, the MIC for growing bacteria in the circulating water immediately after the test and the M for growing bacteria in the circulating water after the test is completed.
The results of all IC measurements are also shown. For comparison, cases where A and B were tested individually are also shown. Table-2
As a result, it is understood that the slime control effect is improved, resistance is less likely to develop, and long-term use is possible.

表−2Table-2

【図面の簡単な説明】[Brief explanation of drawings]

図は、インチアゾロン糸化合r#(5)とブロモニトロ
アルコール孫化合’a CB)との併用による相乗りけ
示したものである。
The figure shows the synergistic effects of the combined use of the intiazolone yarn compound r#(5) and the bromonitroalcohol grand compound 'a CB).

Claims (1)

【特許請求の範囲】[Claims] 1、 インチアゾロン系化合物とブロモニトロアルコー
ル系化合物と金含む抗菌剤。
1. An antibacterial agent containing inthiazolone compounds, bromonitroalcohol compounds, and gold.
JP19360383A 1983-10-17 1983-10-17 Antimicrobial agent Pending JPS6084203A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP19360383A JPS6084203A (en) 1983-10-17 1983-10-17 Antimicrobial agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP19360383A JPS6084203A (en) 1983-10-17 1983-10-17 Antimicrobial agent

Publications (1)

Publication Number Publication Date
JPS6084203A true JPS6084203A (en) 1985-05-13

Family

ID=16310687

Family Applications (1)

Application Number Title Priority Date Filing Date
JP19360383A Pending JPS6084203A (en) 1983-10-17 1983-10-17 Antimicrobial agent

Country Status (1)

Country Link
JP (1) JPS6084203A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH049305A (en) * 1989-05-17 1992-01-14 Katayama Chem Works Co Ltd Aqueous preparation of isothiazolone
JPH0451959A (en) * 1990-06-19 1992-02-20 Nippon Soda Co Ltd Treating agent for circulation type toilet
JP2001261509A (en) * 2000-03-17 2001-09-26 Kurita Water Ind Ltd Industrial antimicrobial agent composition and industrial antimicrobial method
WO2002074087A1 (en) * 2001-03-15 2002-09-26 Bayer Aktiengesellschaft Microbicidal mixtures
JP2013040203A (en) * 2012-11-12 2013-02-28 Aquas Corp Medicine for killing ameba, and method for controlling ameba

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53118527A (en) * 1977-03-28 1978-10-17 Permachem Asia Ltd Bactericide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53118527A (en) * 1977-03-28 1978-10-17 Permachem Asia Ltd Bactericide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH049305A (en) * 1989-05-17 1992-01-14 Katayama Chem Works Co Ltd Aqueous preparation of isothiazolone
JPH0451959A (en) * 1990-06-19 1992-02-20 Nippon Soda Co Ltd Treating agent for circulation type toilet
JP2001261509A (en) * 2000-03-17 2001-09-26 Kurita Water Ind Ltd Industrial antimicrobial agent composition and industrial antimicrobial method
JP4552165B2 (en) * 2000-03-17 2010-09-29 栗田工業株式会社 Industrial antibacterial agent composition and industrial antibacterial method
WO2002074087A1 (en) * 2001-03-15 2002-09-26 Bayer Aktiengesellschaft Microbicidal mixtures
JP2013040203A (en) * 2012-11-12 2013-02-28 Aquas Corp Medicine for killing ameba, and method for controlling ameba

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