CA2268928A1 - Blend of appropriate preservative agents for analysis instruments with ion-selective electrodes - Google Patents
Blend of appropriate preservative agents for analysis instruments with ion-selective electrodes Download PDFInfo
- Publication number
- CA2268928A1 CA2268928A1 CA002268928A CA2268928A CA2268928A1 CA 2268928 A1 CA2268928 A1 CA 2268928A1 CA 002268928 A CA002268928 A CA 002268928A CA 2268928 A CA2268928 A CA 2268928A CA 2268928 A1 CA2268928 A1 CA 2268928A1
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- CA
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- Prior art keywords
- preservative
- oxaban
- ion
- present
- reagents
- 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.)
- Abandoned
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Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
The inventive preservative agent for reagents intended for the diagnostic determination of electrolytes by means of ion-selective electrodes contains a compound which triggers the cleavage of formaldehyde, possibly combined with chloracetamide. The present invention also relates to this blend of preservative agents as well as to the preserved reagents.
Description
Suitable preservative mixture for analyzers with ion selective electrodes Description The present invention concerns preservatives for reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes, their use for preserving the said reagents and reagents to which the preservatives according to the invention have been added.
The determination of electrolytes with the aid of ion-selective electrodes is preferably carried out in flow-through systems which are very vulnerable to any type of microbial contamination. The growth of microorganisms within the system leads to falsifications of the analytical results and with increasing growth of the microorganisms to an inactivation of the electrodes. It is therefore desirable to preserve the reagents used in such flow-through systems.
However, for several reasons it is difficult to preserve the reagents used in the flow-through systems:
1) The diluent used to dilute the samples must not contain any of the electrolytes to be determined or substances that are co-detected by the electrodes due to low selectivity. Unfortunately many biocides cleave off for example C1- or Br' which falsifies the results especially when this process proceeds continuously.
" CA 02268928 1999-04-15 2) The performance as well as the life time of the ion-selective electrodes is impaired by almost all preservatives. The concentration that is tolerated by the electrodes varies from electrode type to electrode type. However, the concentration tolerated by the electrodes is often no longer adequate with regard to its biocidal effectiveness.
The determination of electrolytes with the aid of ion-selective electrodes is preferably carried out in flow-through systems which are very vulnerable to any type of microbial contamination. The growth of microorganisms within the system leads to falsifications of the analytical results and with increasing growth of the microorganisms to an inactivation of the electrodes. It is therefore desirable to preserve the reagents used in such flow-through systems.
However, for several reasons it is difficult to preserve the reagents used in the flow-through systems:
1) The diluent used to dilute the samples must not contain any of the electrolytes to be determined or substances that are co-detected by the electrodes due to low selectivity. Unfortunately many biocides cleave off for example C1- or Br' which falsifies the results especially when this process proceeds continuously.
" CA 02268928 1999-04-15 2) The performance as well as the life time of the ion-selective electrodes is impaired by almost all preservatives. The concentration that is tolerated by the electrodes varies from electrode type to electrode type. However, the concentration tolerated by the electrodes is often no longer adequate with regard to its biocidal effectiveness.
3) The spectrum of microorganisms which can occur in such a system extends from bacteria, yeasts through to fungi. Experience has therefore shown that a single preservative is not sufficient to protect the system against the entire spectrum of microorganisms.
4) Preservatives that come into consideration can often not be used worldwide due to country-specific legal restrictions (such as formaldehyde, antibiotics).
Hence the object of the present invention was to provide preservatives which can be used worldwide and are compatible for all electrodes and whose preservative properties cover the widest possible spectrum of microorganisms and minimize the formation of resistant microorganisms.
This object is achieved according to the invention by a preservative for reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes which contain at least one compound which cleaves off formaldehyde optionally in combination with chloroacetamide as the active substance. Compounds which cleave off formaldehyde have the major advantage over using formaldehyde itself that formaldehyde is only formed in the reagent usually in low amounts which is in turn consumed when it attacks the microbes and hence there are always only low amounts of formaldehyde in the solution. Especially in countries where the use of formaldehyde is generally forbidden, it is possible in this manner to nevertheless utilize the good preservative action of formaldehyde although it is not used directly and is formed in the reagent only in extremely low amounts and is continuously consumed.
Hence one observes the preservative action of formaldehyde although the substance itself is practically only present in extremely small amounts.
According to the invention compounds which cleave off formaldehyde are preferred which only slowly cleave off formaldehyde in small amounts.
Particularly preferred compounds have the formula I
R~
N
in which R1 and R2 represent a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms which can optionally contain heteroatoms and R3 represents H or a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms where one of R1 and R2 can optionally also form a ring closure with R3.
Within the scope of the present invention it has turned out that combinations with chloroacetamide can further increase the biocidal action without adverse effects on all three ion-selective electrodes.
Particularly preferred compounds within the scope of the present invention are Oxaban A* and Oxaban E** (*4,4-dimethyl-1,3-oxazolidine, **
Et ~~0 1 ~, N
Especially Oxaban E already has a very good preservative action when used alone.
However, a combination with chloroacetamide can also in the case of Oxaban E lead to an extension of the spectrum of activities and increase the activity.
Surprisingly it has turned out that the preservatives according to the invention at a concentration that can be used without problems for the electrodes not only has a biocidal action on a large spectrum of different microorganisms but at the same time also does not have an adverse effect on the life time of the electrodes. In a preferred embodiment of the invention the preservative contains the preserving substances at such a concentration that, in the reagents to be preserved, chloroacetamide is present at a concentration of 0.1 to 0.5 mg/ml or/and Oxaban E is present at a concentration of 0.1 to 3 mg/ml or/and Oxaban A is present at a concentration of 0.2 to 1 mg/ml. For this purpose it is also possible to particularly advantageously use a concentrate of the preservative with a ca. 10- to 100-fold concentration of the ingredients. This concentrate can than be introduced into the reagents to be preserved without substantially changing the concentration of the compounds contained therein. Using the said final concentrations for the reagents to be preserved no adverse effects whatsoever on the electrodes are to be expected. Hence the advantages of the preservatives according to the invention are:
- No influence on the performance of all three ion-selective electrodes over their life time. This is important since it is only possible to use all three electrodes simultaneously.
- Adequate preservative properties at the concentration to be used.
- Effective biocidal properties at an optimal pH value for the electrodes of pH 7.0 to 8.2.
- Better avoidance of resistance development by the preferred use of two biocides (formaldehyde cleaver and chloroacetamide).
- Avoidance of legal restrictions in various countries.
In the preservative according to the invention the substances are particularly preferably present in such an amount that chloroacetamide is present in the reagents to be preserved in an amount of 0.1 to 0.4 mg/ml or/and Oxaban E is present in an amount of 0.5 to 1.5 mg/ml or/and Oxaban A is present in an amount of 0.3 to 0.8 mg/ml.
As already mentioned the preservative according to the invention is advantageous since it ensures a very effective preservation without influencing the ion-selective electrodes. Hence a further subject matter of the present invention is the use of the preservative according to the invention to preserve reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes.
Yet a further subject matter of the present invention is a reagent for the diagnostic determination of electrolytes with the aid of ion-selective electrodes which contains a preservative according to the invention. The reagent preserved according to the invention preferably has a pH value of 7.0 to 8.2. The electrodes are not adversely effected within this pH
range with a concurrent optimal action of the preserving agents.
The following example in conjunction with the figures further elucidates the invention.
Example:
Various preservatives were tested for their ability to preserve reagents for the determination of electrolytes with the aid of ion-selective electrodes. In doing so particular attention was paid to possible impairment of the electrodes. The following table 1 shows that only chloroacetamide, Oxaban A and Oxaban E have no effects whatsoever on all three types of electrodes.
The preservative capability of 4,4-dimethyl-1,3-oxazolidine (Oxaban A) and chloroacetamide (CAA) and Oxaban E was examined in further investigations. As a _ 7 _ comparison the microbial growth of a non-preserved composition at pH 7.94 is shown in figure 1.
Figure 2 shows the same composition but with addition of 0.5 mg/ml Oxaban A pH 7.6 and 0.2 mg/ml CAA. It can be clearly seen from figure 2 that fungi as well as both examined types of bacteria are reduced to zero within 6 weeks in the solution. Hence the stated concentration does not only have the ability to prevent growth of germs already present in the solution but severely reduces the germs within a short period.
Figure 3 shows a further investigation in which again the same solution was preserved with 0.3 mg/ml Oxaban A
and 0.12 mg/ml CAA. The pH value of this solution was 8.06. This also shows that bacteria and fungi are in some cases very strongly reduced and in the case of the type 2 bacteria it was at least observed that the number of germs only increased to a negligible extent.
Finally figure 4 shows an even lower concentration of the two preservatives which also prevents growth of the germs.
Figure 5 shows, in comparison to this, preservation with only one of the two preserving components i.e. with 0.5 mg Oxaban A. Whereas a very strong germ-reducing effect was observed with this concentration of Oxaban in combination with CAA in figure 2, such a strong effect is not detected with Oxaban A alone at a concentration of 0.5 mg/ml.
Figures 6 to 14 show the effect of various preservatives on the three types of electrodes. It can be seen that - g -Oxaban A as well as CAA and Oxaban E do not have any effects whatsoever on the electrodes in the functional range preferably used according to the invention whereas other preservatives which are also listed in table 1 have adverse effects at least in the functional ranges required for these preservatives.
Table 1 O - no adverse effect O - small adverse effect O - large adverse effect sodium potassium chloride electrode electrode electrode bromo-nitro-dioxane (BND) O O
methylisothiazolone (MIT) O O
hydroxypyridine oxide (HPO) O O O
imidazolidinyl urea (IZU) ~ O O
chloroacetamide (CAA) O O O
1,2-dibromo-2,4-dicyano- O O
butane and phenoxyethanol (Euxyl K400) 4,4-dimethyl-1,3- O O O
oxazolidine (Oxaban A) Oxaban E O O O
Figures 15 to 19 show the preservative action of Oxaban E. at various concentrations and in combination with CAA.
From this it can be seen that Oxaban E even alone already has a very good preservative action.
Hence the object of the present invention was to provide preservatives which can be used worldwide and are compatible for all electrodes and whose preservative properties cover the widest possible spectrum of microorganisms and minimize the formation of resistant microorganisms.
This object is achieved according to the invention by a preservative for reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes which contain at least one compound which cleaves off formaldehyde optionally in combination with chloroacetamide as the active substance. Compounds which cleave off formaldehyde have the major advantage over using formaldehyde itself that formaldehyde is only formed in the reagent usually in low amounts which is in turn consumed when it attacks the microbes and hence there are always only low amounts of formaldehyde in the solution. Especially in countries where the use of formaldehyde is generally forbidden, it is possible in this manner to nevertheless utilize the good preservative action of formaldehyde although it is not used directly and is formed in the reagent only in extremely low amounts and is continuously consumed.
Hence one observes the preservative action of formaldehyde although the substance itself is practically only present in extremely small amounts.
According to the invention compounds which cleave off formaldehyde are preferred which only slowly cleave off formaldehyde in small amounts.
Particularly preferred compounds have the formula I
R~
N
in which R1 and R2 represent a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms which can optionally contain heteroatoms and R3 represents H or a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms where one of R1 and R2 can optionally also form a ring closure with R3.
Within the scope of the present invention it has turned out that combinations with chloroacetamide can further increase the biocidal action without adverse effects on all three ion-selective electrodes.
Particularly preferred compounds within the scope of the present invention are Oxaban A* and Oxaban E** (*4,4-dimethyl-1,3-oxazolidine, **
Et ~~0 1 ~, N
Especially Oxaban E already has a very good preservative action when used alone.
However, a combination with chloroacetamide can also in the case of Oxaban E lead to an extension of the spectrum of activities and increase the activity.
Surprisingly it has turned out that the preservatives according to the invention at a concentration that can be used without problems for the electrodes not only has a biocidal action on a large spectrum of different microorganisms but at the same time also does not have an adverse effect on the life time of the electrodes. In a preferred embodiment of the invention the preservative contains the preserving substances at such a concentration that, in the reagents to be preserved, chloroacetamide is present at a concentration of 0.1 to 0.5 mg/ml or/and Oxaban E is present at a concentration of 0.1 to 3 mg/ml or/and Oxaban A is present at a concentration of 0.2 to 1 mg/ml. For this purpose it is also possible to particularly advantageously use a concentrate of the preservative with a ca. 10- to 100-fold concentration of the ingredients. This concentrate can than be introduced into the reagents to be preserved without substantially changing the concentration of the compounds contained therein. Using the said final concentrations for the reagents to be preserved no adverse effects whatsoever on the electrodes are to be expected. Hence the advantages of the preservatives according to the invention are:
- No influence on the performance of all three ion-selective electrodes over their life time. This is important since it is only possible to use all three electrodes simultaneously.
- Adequate preservative properties at the concentration to be used.
- Effective biocidal properties at an optimal pH value for the electrodes of pH 7.0 to 8.2.
- Better avoidance of resistance development by the preferred use of two biocides (formaldehyde cleaver and chloroacetamide).
- Avoidance of legal restrictions in various countries.
In the preservative according to the invention the substances are particularly preferably present in such an amount that chloroacetamide is present in the reagents to be preserved in an amount of 0.1 to 0.4 mg/ml or/and Oxaban E is present in an amount of 0.5 to 1.5 mg/ml or/and Oxaban A is present in an amount of 0.3 to 0.8 mg/ml.
As already mentioned the preservative according to the invention is advantageous since it ensures a very effective preservation without influencing the ion-selective electrodes. Hence a further subject matter of the present invention is the use of the preservative according to the invention to preserve reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes.
Yet a further subject matter of the present invention is a reagent for the diagnostic determination of electrolytes with the aid of ion-selective electrodes which contains a preservative according to the invention. The reagent preserved according to the invention preferably has a pH value of 7.0 to 8.2. The electrodes are not adversely effected within this pH
range with a concurrent optimal action of the preserving agents.
The following example in conjunction with the figures further elucidates the invention.
Example:
Various preservatives were tested for their ability to preserve reagents for the determination of electrolytes with the aid of ion-selective electrodes. In doing so particular attention was paid to possible impairment of the electrodes. The following table 1 shows that only chloroacetamide, Oxaban A and Oxaban E have no effects whatsoever on all three types of electrodes.
The preservative capability of 4,4-dimethyl-1,3-oxazolidine (Oxaban A) and chloroacetamide (CAA) and Oxaban E was examined in further investigations. As a _ 7 _ comparison the microbial growth of a non-preserved composition at pH 7.94 is shown in figure 1.
Figure 2 shows the same composition but with addition of 0.5 mg/ml Oxaban A pH 7.6 and 0.2 mg/ml CAA. It can be clearly seen from figure 2 that fungi as well as both examined types of bacteria are reduced to zero within 6 weeks in the solution. Hence the stated concentration does not only have the ability to prevent growth of germs already present in the solution but severely reduces the germs within a short period.
Figure 3 shows a further investigation in which again the same solution was preserved with 0.3 mg/ml Oxaban A
and 0.12 mg/ml CAA. The pH value of this solution was 8.06. This also shows that bacteria and fungi are in some cases very strongly reduced and in the case of the type 2 bacteria it was at least observed that the number of germs only increased to a negligible extent.
Finally figure 4 shows an even lower concentration of the two preservatives which also prevents growth of the germs.
Figure 5 shows, in comparison to this, preservation with only one of the two preserving components i.e. with 0.5 mg Oxaban A. Whereas a very strong germ-reducing effect was observed with this concentration of Oxaban in combination with CAA in figure 2, such a strong effect is not detected with Oxaban A alone at a concentration of 0.5 mg/ml.
Figures 6 to 14 show the effect of various preservatives on the three types of electrodes. It can be seen that - g -Oxaban A as well as CAA and Oxaban E do not have any effects whatsoever on the electrodes in the functional range preferably used according to the invention whereas other preservatives which are also listed in table 1 have adverse effects at least in the functional ranges required for these preservatives.
Table 1 O - no adverse effect O - small adverse effect O - large adverse effect sodium potassium chloride electrode electrode electrode bromo-nitro-dioxane (BND) O O
methylisothiazolone (MIT) O O
hydroxypyridine oxide (HPO) O O O
imidazolidinyl urea (IZU) ~ O O
chloroacetamide (CAA) O O O
1,2-dibromo-2,4-dicyano- O O
butane and phenoxyethanol (Euxyl K400) 4,4-dimethyl-1,3- O O O
oxazolidine (Oxaban A) Oxaban E O O O
Figures 15 to 19 show the preservative action of Oxaban E. at various concentrations and in combination with CAA.
From this it can be seen that Oxaban E even alone already has a very good preservative action.
Claims (10)
1. Preservative for reagents for the diagnostic determination of electrolytes with the aid of ion- selective electrodes, wherein it contains at least one compound which cleaves off formaldehyde in combination with chloroacetamide as the active substance, wherein the preservative does not have an adverse effect on the performance of the electrodes.
2. Preservative as claimed in claim 1, wherein the compound which cleaves off formaldehyde corresponds to the following general formula:
in which R1 and R2 represent a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms which can optionally contain heteroatoms and R3 represents H or a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms where one of R1 and R2 can optionally also form a ring closure with R3.
in which R1 and R2 represent a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms which can optionally contain heteroatoms and R3 represents H or a branched or unbranched alkyl, alkenyl or alkinyl group with 1 to 6 C atoms where one of R1 and R2 can optionally also form a ring closure with R3.
3. Preservative as claimed in claim 1 or 2, wherein the compound of formula (I) is Oxaban A or Oxaban E.
4. Preservative as claimed in claim 1, wherein it contains the active substance or active substances at such a concentration that in the reagents to be preserved chloroacetamide is present in an amount of 0.1 to 0.5 mg/ml or/and Oxaban E is present in an amount of 0.1 to 3 mg/ml or/and Oxaban A is present in an amount of 0.2 to 1 mg/ml.
5. Preservative as claimed in claim 2, wherein in the reagents to be preserved chloroacetamide is present in an amount of 0.1 to 0.4 mg/ml or/and Oxaban E is present in an amount of 0.5 to 1.5 mg/ml or/and Oxaban A is present in an amount of 0.3 to 0.8 mg/ml.
6. Use of a preservative as claimed in one of the claims 1 to 5 for preserving reagents for the diagnostic determination of electrolytes with the aid of ion-selective electrodes.
7. Reagent for the diagnostic determination of electrolytes with the aid of ion-selective electrodes, wherein it contains a preservative mixture as claimed in one of the claims 1 to 5.
8. Reagent as claimed in claim 7, wherein it has a pH value of 7.0 to 8.2.
9. Use of a preservative containing at least one compound which cleaves off formaldehyde optionally in combination with chloroacetamide as the active substance to improve the performance of ion- selective electrodes for the diagnostic determination of electrolytes.
10. Use as claimed in claim 9, wherein the compound which cleaves off formaldehyde and chloroacetamide are used.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19643927.2 | 1996-10-30 | ||
| DE1996143927 DE19643927A1 (en) | 1996-10-30 | 1996-10-30 | Suitable preservative mix for analyzers with ion-selective electrodes |
| PCT/EP1997/006011 WO1998018327A1 (en) | 1996-10-30 | 1997-10-30 | Blend of appropriate preservative agents for analysis instruments with ion-selective electrodes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2268928A1 true CA2268928A1 (en) | 1998-05-07 |
Family
ID=7809678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002268928A Abandoned CA2268928A1 (en) | 1996-10-30 | 1997-10-30 | Blend of appropriate preservative agents for analysis instruments with ion-selective electrodes |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0944316A2 (en) |
| JP (1) | JP2001503515A (en) |
| AU (1) | AU718943B2 (en) |
| CA (1) | CA2268928A1 (en) |
| DE (1) | DE19643927A1 (en) |
| WO (1) | WO1998018327A1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2218348A1 (en) * | 1972-04-15 | 1973-10-31 | Henkel & Cie Gmbh | USE OF BICYCLIC OXAZOLIDINES AS ANTIMICROBIAL ACTIVE INGREDIENTS |
| US4088655A (en) * | 1974-05-13 | 1978-05-09 | Imc Chemical Group, Inc. | N-substituted nitroalkyl oxazolidine |
| US5464850A (en) * | 1991-10-04 | 1995-11-07 | Ciba Corning Diagnostics Corp. | Synergistic preservative systems for chemistry reagents |
-
1996
- 1996-10-30 DE DE1996143927 patent/DE19643927A1/en not_active Withdrawn
-
1997
- 1997-10-30 JP JP52006398A patent/JP2001503515A/en active Pending
- 1997-10-30 AU AU53150/98A patent/AU718943B2/en not_active Ceased
- 1997-10-30 EP EP97950054A patent/EP0944316A2/en not_active Withdrawn
- 1997-10-30 CA CA002268928A patent/CA2268928A1/en not_active Abandoned
- 1997-10-30 WO PCT/EP1997/006011 patent/WO1998018327A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE19643927A1 (en) | 1998-05-07 |
| WO1998018327A1 (en) | 1998-05-07 |
| EP0944316A2 (en) | 1999-09-29 |
| AU718943B2 (en) | 2000-05-04 |
| JP2001503515A (en) | 2001-03-13 |
| AU5315098A (en) | 1998-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |