CA1058199A - Certain oxime carbonates and method of controlling sulfate reducing bacteria - Google Patents
Certain oxime carbonates and method of controlling sulfate reducing bacteriaInfo
- Publication number
- CA1058199A CA1058199A CA243,710A CA243710A CA1058199A CA 1058199 A CA1058199 A CA 1058199A CA 243710 A CA243710 A CA 243710A CA 1058199 A CA1058199 A CA 1058199A
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- Prior art keywords
- compound
- bacteria
- growth
- sulfate reducing
- reducing bacteria
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
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- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Abstract of the Disclosure Compounds having the formula in which R is alkyl having from 1 to 6 carbon atoms. The compounds are useful in inhibiting the growth of bacteria and fungi.
Also, a method of inhibiting the growth of sulfate reducing bacteria by contacting said bacteria with an effec-tive amount of the compound 1,3-dichloroacetoneoxime acetate or 1,3-dichloroacetoneoxime propionate.
Also, a method of inhibiting the growth of sulfate reducing bacteria by contacting said bacteria with an effec-tive amount of the compound 1,3-dichloroacetoneoxime acetate or 1,3-dichloroacetoneoxime propionate.
Description
0 5 ~1.9 9 Description of the Invention This invention relates to novel chemical compounds and to their use in controlling fungi and bacteria. More particularly, the chemical compounds are certain keto oxime carbona~es. Also, this invention relates to a method of inhibiting the growth of sulfate reducing bacteria.
The compounds of the present invention are those having the formula ClCH2\
\C=N-O- 11 -O-R
ClCH /
in which R is alkyl having from l to 6 carbon atoms.
The compounds of the present invention can be pre-pared by reacting a compound of the formula ClCH2\
/C=NOH
ClCH2 with a compound of the formula O
Halo-C-0-R
in which halo is chlorine or bromine and R is as defined.
Preferably, the reaction is carried out in the presence of a base such as pyridine and in a solvent for the reactants. Generally, the reaction is exothermic so no heating is required. Cooling is sometimes required to control lOS~3~99 the reaction rate. The compounds of this invention can be recovered from the mixture and purified by standard procedures.
Compounds of the formula N-OH
ClCH2-C-CH2Cl can be prepared by reacting Cl-CH2-C-CH2Cl with excess hydroxylamine hydrochloride or hydroxylamine hydrobromide in ethanol and water. The reaction can be run with heating under reflux for several hours. The desired product is recovered and purified by conventional techniques.
Example 1 1,3-dichloroacetoneoxime 63.5 grams (0.50 mole) 1,3-dichloropropanone, 69.5 grams (1.00 mole) hydroxylamine hydrochloride, 250 ml.
ethanol and 25 ml. of water were combined and heated under reflux for four hours. The cooled mixture was poured into 500 ml. of water. The aqueous solution was extracted with three 100 ml. portions of chloroformr The chloroform phases were combined and dried with anhydrous MgS04. The chlorofonm was evaporated to give 66.3 g. (93.6% theory) of 1,3-dichloro-acetoneoxime, ClCH2 C=NOH
ClCH /
N30 = 1.5044.
Example 2 1,3-dichloroacetoneoxim-e O-methyl carbonate 14.1 grams (0.10 mole) 1,3-dichloroacetoneoxime, 10.1 grams (0.13 mole) methylchloroformate were combined in 200 ml. of benzene. The mixture was stirred with cooling at 13 to 14C. for 20 minutes with 18.1 ml. (0.13 mole) of triethyl amine. The mixture was allowed to warm to room temperature. The mixture was washed with two 100 ml. portions of water. The benzene phase was dried with anhydrous MgSO4 and evaporated to give 9.7 g. of 1,3-dichloroacetoneoxime O-methyl carbonate, ClCH2 e C=NOC-OCH3 ClCH2 N D = 1.4722.
The following is a table of certain selected compounds that are preparable according to the procedure described hereto. Compound numbers have been assigned to each compound and are used throughout the remainder of the application.
TABLE I
Compound No. R
l* methyl
The compounds of the present invention are those having the formula ClCH2\
\C=N-O- 11 -O-R
ClCH /
in which R is alkyl having from l to 6 carbon atoms.
The compounds of the present invention can be pre-pared by reacting a compound of the formula ClCH2\
/C=NOH
ClCH2 with a compound of the formula O
Halo-C-0-R
in which halo is chlorine or bromine and R is as defined.
Preferably, the reaction is carried out in the presence of a base such as pyridine and in a solvent for the reactants. Generally, the reaction is exothermic so no heating is required. Cooling is sometimes required to control lOS~3~99 the reaction rate. The compounds of this invention can be recovered from the mixture and purified by standard procedures.
Compounds of the formula N-OH
ClCH2-C-CH2Cl can be prepared by reacting Cl-CH2-C-CH2Cl with excess hydroxylamine hydrochloride or hydroxylamine hydrobromide in ethanol and water. The reaction can be run with heating under reflux for several hours. The desired product is recovered and purified by conventional techniques.
Example 1 1,3-dichloroacetoneoxime 63.5 grams (0.50 mole) 1,3-dichloropropanone, 69.5 grams (1.00 mole) hydroxylamine hydrochloride, 250 ml.
ethanol and 25 ml. of water were combined and heated under reflux for four hours. The cooled mixture was poured into 500 ml. of water. The aqueous solution was extracted with three 100 ml. portions of chloroformr The chloroform phases were combined and dried with anhydrous MgS04. The chlorofonm was evaporated to give 66.3 g. (93.6% theory) of 1,3-dichloro-acetoneoxime, ClCH2 C=NOH
ClCH /
N30 = 1.5044.
Example 2 1,3-dichloroacetoneoxim-e O-methyl carbonate 14.1 grams (0.10 mole) 1,3-dichloroacetoneoxime, 10.1 grams (0.13 mole) methylchloroformate were combined in 200 ml. of benzene. The mixture was stirred with cooling at 13 to 14C. for 20 minutes with 18.1 ml. (0.13 mole) of triethyl amine. The mixture was allowed to warm to room temperature. The mixture was washed with two 100 ml. portions of water. The benzene phase was dried with anhydrous MgSO4 and evaporated to give 9.7 g. of 1,3-dichloroacetoneoxime O-methyl carbonate, ClCH2 e C=NOC-OCH3 ClCH2 N D = 1.4722.
The following is a table of certain selected compounds that are preparable according to the procedure described hereto. Compound numbers have been assigned to each compound and are used throughout the remainder of the application.
TABLE I
Compound No. R
l* methyl
2 ethyl
3 n-butyl
4 hexyl *Prepared in Example 2 :` ~
~ 30 105S~g9 In Vitro Vial Test The following test illustrates utility of the compounds in controlling fungi and bacteria. This test measures the bactericidal and fungicidal properties of a compound when in contact with a growing bacterium or fungus.
The test is conducted by partially filling two l-ounce vials with malt broth and one l-ounce vial with nutrient broth.
Next the test compound is added to the vials at a certain concentration, expressed in parts permillion, and mixed with the broth. A water suspension of spores of the desired fungi or cells of the desired bacteria (one organism per vial) is added. The vials are then sealed and incubated for one week; at this time the vials are examined and the results recorded. Table II shows the results of various compounds tested by the In Vitro Vial Test, partial control of the test organism is indicated by parentheses. In such a case, complete control was observed at the next higher concentration.
Table II
Concentration (p.p.m.) Which Inhibited Growth Compound Aspergillus Penicillium Escherichia Staphylococcus Numberniger italicum coli aureus 1(.25) (-25) >50 25 2.125 (.125) >50 5 3.125 (1) >50 25 Sulfate reducing bacteria are anaerobic, i.e. they can thrive in the absence of free oxygen. They are described as sulfate reducing since in their life metabolism they reduce 1~ 5 ~ 1 9 ~
the sulfate ion found in most waters to hydrogen sulfide.
Moreover, these bacteria are resistant or develop resistance to many bacteriostatic and bactericidal agents. Frequently, sulfate reducing bacteria multiply so rapidly, particularly under moist, humid conditions and in a saline environment, that the concentration of known bactericides, e.g., chlorine, required for control becomes so high as itself to cause cor-rosion of unprotected steel equipment.
The sulfate reducing bacteria generally include the species Desulfovibrio desulfuricans, Desulfovibrio ori-entis, Clostridium ni~rificans. Of these, the first is most prevalent.
By "process water" is meant fresh water, slightly saline water, sea water, or concentrated brines, which are utilized in or result from various industrial treatments and whlch-because of their source, mode of storage or utilization, operate as culture media for sulfate reducing bacteria.
Typical industrial systems employing process water are metallurgical operations employing cutting oils, latex paint preparation and storage, oil production including sub-surface disposal of water withdrawn from wells and water used to repressurize wells for secondary oil recovery, packing fluids employed as "dead" layers in the casing of "multiple completion" oil well systems, and neutral drilling mud systems.
In general, any process water which remains quiescent or under reduced rate of flow is subject to growth of sulfate reducing bacteria.
105~99 The harmful effects of growth of these bacteria are enormous. In oil production, for example, the bacteria cause injection well plugging and corrosion of iron and steel pipes and equipment, necessitating expensive shut-down for cleaning. Using the oil as their carbon source, the bacteria reduce sulfate ion ~o hydrogen sulfide ("sour gas") which in turn reacts with iron to form black particles of suspended iron sulfide. These particles clog the injection system and the once water-permeable oil-bearing formations.
The bacteria are often the sole cause of pitting type corro-sion of drilling equipment, either by acting as cathode de-polarizers or by producing corrosive hydrogen sulfide, but more often they accelerate corrosion. See A. W. Baumgartner, "Sulfate-Reducing Bacteria ... Their Role in Corrosion and Well Plugging," presentation at West Texas Oil Lifting Short Course, Texas Technological College, Lubbock, Texas, April 21-22, 1960.
Saline water, e.g. brine or sea water, is commonly employed in primary and secondary oil recovery and as a packing fluid in multiple completion oil well, particularly in coastal areas. Saline water, however, greatly limits the choice of bactericidal agents effective against sulfate reducing bacteria since many of such agents, e.g., amines, quaternary compounds, imidazolines, precipitate out in salt solutions. Others, e.g., silver and mercury compounds, such as phenyl mercuric acetate, are precipitated by the sulfides resulting rom the metabolism of the bacteria.
The problem of effective bactericides in brine systems is further complicated by the fact that saline solutions encourage bacterial growth by removing constituents deleterious to bacterial growth.
In metallurgical operations, shutdown of a plant over a weekend, for example, has permitted the growth of sulfate reducing bacteria in cutting oil tanks, causing unbearable odors of hydrogen sulfide and loss of production time while the cutting oils are replaced and tanks cleaned.
Several requirements for usefulness of a bactericide against sulfate reducing bacteria in the process water must be met. Thus, the antibacterial agent must not only rapidly and effectively inhibit growth of sulfate reducing bacteria, but control must be effective at economically low concentrations.
Additionally, the compound must be compatible with the process water. In particular, it should not salt out in brine solutions or react with other constituents so as to promote plugging. Nor should it coat the filters used, for example, to separate secondary oil from waterfloods. The antibacterial agent must be non-toxic both to personnel and to livestock which may drink from reservoirs. And finally, the agent remaining in the oil separated from waterfloods must not poison the cracking catalysts employed in refinin~ oil.
The unpredictability of activity of compounds against sulfate reducing bacteria is well known. For example, a wide variation in activity against the same and different sulfate reducing bacterial strains has been noted for imidazolines, quaternaries, chlorinated phenols, amines and glutaraldehyde and hence it was not possible to predict the activity of one bactericide from knowledge of activity of another bactericide. See, for example, "Sulfate-Reducing Bacteria: Their Relation to the Secondary Recovery of Oil", Science Symposium, St. Bonaventure University October 23-24, 1058~9~
1957, particularly page 6~.
In accordance with the present invention a method is provided for inhibiting the growth of sulfate reducing bacteria, and the consequent fouling of process water containing said bacteria, which comprises contacting said bacteria with an effective amount of one of the following compounds:
1,3-dichloroacetoneoxime acetate ClCH2 0 C=NO-C-CH3 ClCH2 1-3-dichloroacetoneoxime propionate ClCH2 0 C=NO-C-C2H2 ClCH2 /
These compounds are known to be useful in controlling aerobic bacteria as taught in U.S. 3,733,419.
The amount of compound for effective control will depend on the particular system in which the process water is employed. Oil well brines used in oil recovery require in the order of 25 p.p.m. or less. Neutral drilling muds are protected against growth of sulfate reducing bacteria by about 50 p.p.m. or less of one of the compounds. Amounts of 150 p.p.m.
less in cutting oils effectively prevent spoilage and offensive odors therein. Generally, the compounds are effective in quantities of the order of about 0.25 to 10,000 p.p.m.
The compounds of the invention may be added directly to the process water in any suitable tank. However, even though lOS8~5~9 the maximum concentrations used are small, the volumes are large and uniform mixing is highly desirable. The most useful mode of addition is to prepare a relatively smaller, but more concen-trated solution than the final dilution desired. This solution can then be metered by a proportioning pump or its equivalent into a suitably agitated tank or flow of water as the latter is being pumped to the point of use. Normal turbulent flow in the conduit produces adequate mixing. In this way, accurate dosages can be supplied and uniform dilutions obtained.
If desired, any of the numerous well known additives may be employed with the compounds provided they are compatible therewith. It may be useful to aid dispersion of a compound by addition of conventional surfactants in order to prepare concentrated suspensions or emulsions, aqueous or nonaqueous, prior to addition to the process water. Suitable dispersions may be prepared by agitating the compounds in the presence of a sur-factant such as sodium lauryl sulfate, aliphatic and aromatic sulfonates, e.g., sulfonated castor oil, or various alkaryl sulfonates, e.g. the sodium salt of mono sulfonated nonyl naphthalene. Non-ionic types of emulsifying agents such as the higher molecular weight alkyl polyglycol ethers and analogous thio ethers such as the decyl, dodecyl and tetradecyl polyglycol ethers and thio ethers containing from about 25 to 75 carbon atoms may be used. The concentration of surfactant in the final emulsion should be sufficient to make the oil and water phases readily dispersible. For purposes of forming a spray emulsion, from about 0.02 to 3~ of the surfactant will be effec-tive. In general, formulations containing a surface active agent in the amount of from 1 to 20~ by weight of active ingredient are satisfactory although such proportion may be varied over a wide range of proportions depending upon the particular ~()581~
circumstance.
Adjuvants such as wetting agents or humectants may, if desired, be employed particularly when compounding an aqueous dispersion. Examples of humectants are glycerine, diethylene glycol, polyethylene glycol and the like.
Sulfate Reducing Bacteria in Vitro Test This test measures the bac~ericidal properties of a compound when in contact with a sulfate reducing bacteria, specifically Desulfovibrio desulfuricans. The test is con-ducted by dissolving the test compound in acetone to give an 0.5~ solution. This toxicant is added to vials containing sterile Sulfate API broth with tryptone under anaerobic con-ditions at such levels to give final toxicant concentrations of 1, 5, 10 and 50 ~g/ml. of solution. An inoculant solution of 0.5 ml. of the growing organism, Desulfovibrio desulfuricans, is added to the vials followed by sufficient sterile distilled water to give a total of 10 ml. of solution in the vials. The vials are incubated at room temperature for 3 to 5 days until untreated controls show growth of the organism as indicated by the black color development in the vials.
The following is a summary of the minimum inhibitory concentration necessary to control the organism.
Compound Minimum Inhibitory Conc ~g/ml 1,3-dichloroacetoneoxime acetate 5 1,3-dichloroacetoneoxime propionate 1*
Compound Number 2 5 *lowest concentration tested ---` io5~99 As can be seen by the test results, the compounds find particular utility as bactericides and fungicides. The compounds can be applied in a variety of ways at various concentrations. They can be combined with suitable carriers and applied as dusts, sprays, or drenches. The amount applied will depend on the nature of the utility. The rate of application can also vary with the microbiological use intended.
The problems associated with sulfate reducing bacteria and method of application for the control thereof are described in U.S. 3,300,375.
~ 30 105S~g9 In Vitro Vial Test The following test illustrates utility of the compounds in controlling fungi and bacteria. This test measures the bactericidal and fungicidal properties of a compound when in contact with a growing bacterium or fungus.
The test is conducted by partially filling two l-ounce vials with malt broth and one l-ounce vial with nutrient broth.
Next the test compound is added to the vials at a certain concentration, expressed in parts permillion, and mixed with the broth. A water suspension of spores of the desired fungi or cells of the desired bacteria (one organism per vial) is added. The vials are then sealed and incubated for one week; at this time the vials are examined and the results recorded. Table II shows the results of various compounds tested by the In Vitro Vial Test, partial control of the test organism is indicated by parentheses. In such a case, complete control was observed at the next higher concentration.
Table II
Concentration (p.p.m.) Which Inhibited Growth Compound Aspergillus Penicillium Escherichia Staphylococcus Numberniger italicum coli aureus 1(.25) (-25) >50 25 2.125 (.125) >50 5 3.125 (1) >50 25 Sulfate reducing bacteria are anaerobic, i.e. they can thrive in the absence of free oxygen. They are described as sulfate reducing since in their life metabolism they reduce 1~ 5 ~ 1 9 ~
the sulfate ion found in most waters to hydrogen sulfide.
Moreover, these bacteria are resistant or develop resistance to many bacteriostatic and bactericidal agents. Frequently, sulfate reducing bacteria multiply so rapidly, particularly under moist, humid conditions and in a saline environment, that the concentration of known bactericides, e.g., chlorine, required for control becomes so high as itself to cause cor-rosion of unprotected steel equipment.
The sulfate reducing bacteria generally include the species Desulfovibrio desulfuricans, Desulfovibrio ori-entis, Clostridium ni~rificans. Of these, the first is most prevalent.
By "process water" is meant fresh water, slightly saline water, sea water, or concentrated brines, which are utilized in or result from various industrial treatments and whlch-because of their source, mode of storage or utilization, operate as culture media for sulfate reducing bacteria.
Typical industrial systems employing process water are metallurgical operations employing cutting oils, latex paint preparation and storage, oil production including sub-surface disposal of water withdrawn from wells and water used to repressurize wells for secondary oil recovery, packing fluids employed as "dead" layers in the casing of "multiple completion" oil well systems, and neutral drilling mud systems.
In general, any process water which remains quiescent or under reduced rate of flow is subject to growth of sulfate reducing bacteria.
105~99 The harmful effects of growth of these bacteria are enormous. In oil production, for example, the bacteria cause injection well plugging and corrosion of iron and steel pipes and equipment, necessitating expensive shut-down for cleaning. Using the oil as their carbon source, the bacteria reduce sulfate ion ~o hydrogen sulfide ("sour gas") which in turn reacts with iron to form black particles of suspended iron sulfide. These particles clog the injection system and the once water-permeable oil-bearing formations.
The bacteria are often the sole cause of pitting type corro-sion of drilling equipment, either by acting as cathode de-polarizers or by producing corrosive hydrogen sulfide, but more often they accelerate corrosion. See A. W. Baumgartner, "Sulfate-Reducing Bacteria ... Their Role in Corrosion and Well Plugging," presentation at West Texas Oil Lifting Short Course, Texas Technological College, Lubbock, Texas, April 21-22, 1960.
Saline water, e.g. brine or sea water, is commonly employed in primary and secondary oil recovery and as a packing fluid in multiple completion oil well, particularly in coastal areas. Saline water, however, greatly limits the choice of bactericidal agents effective against sulfate reducing bacteria since many of such agents, e.g., amines, quaternary compounds, imidazolines, precipitate out in salt solutions. Others, e.g., silver and mercury compounds, such as phenyl mercuric acetate, are precipitated by the sulfides resulting rom the metabolism of the bacteria.
The problem of effective bactericides in brine systems is further complicated by the fact that saline solutions encourage bacterial growth by removing constituents deleterious to bacterial growth.
In metallurgical operations, shutdown of a plant over a weekend, for example, has permitted the growth of sulfate reducing bacteria in cutting oil tanks, causing unbearable odors of hydrogen sulfide and loss of production time while the cutting oils are replaced and tanks cleaned.
Several requirements for usefulness of a bactericide against sulfate reducing bacteria in the process water must be met. Thus, the antibacterial agent must not only rapidly and effectively inhibit growth of sulfate reducing bacteria, but control must be effective at economically low concentrations.
Additionally, the compound must be compatible with the process water. In particular, it should not salt out in brine solutions or react with other constituents so as to promote plugging. Nor should it coat the filters used, for example, to separate secondary oil from waterfloods. The antibacterial agent must be non-toxic both to personnel and to livestock which may drink from reservoirs. And finally, the agent remaining in the oil separated from waterfloods must not poison the cracking catalysts employed in refinin~ oil.
The unpredictability of activity of compounds against sulfate reducing bacteria is well known. For example, a wide variation in activity against the same and different sulfate reducing bacterial strains has been noted for imidazolines, quaternaries, chlorinated phenols, amines and glutaraldehyde and hence it was not possible to predict the activity of one bactericide from knowledge of activity of another bactericide. See, for example, "Sulfate-Reducing Bacteria: Their Relation to the Secondary Recovery of Oil", Science Symposium, St. Bonaventure University October 23-24, 1058~9~
1957, particularly page 6~.
In accordance with the present invention a method is provided for inhibiting the growth of sulfate reducing bacteria, and the consequent fouling of process water containing said bacteria, which comprises contacting said bacteria with an effective amount of one of the following compounds:
1,3-dichloroacetoneoxime acetate ClCH2 0 C=NO-C-CH3 ClCH2 1-3-dichloroacetoneoxime propionate ClCH2 0 C=NO-C-C2H2 ClCH2 /
These compounds are known to be useful in controlling aerobic bacteria as taught in U.S. 3,733,419.
The amount of compound for effective control will depend on the particular system in which the process water is employed. Oil well brines used in oil recovery require in the order of 25 p.p.m. or less. Neutral drilling muds are protected against growth of sulfate reducing bacteria by about 50 p.p.m. or less of one of the compounds. Amounts of 150 p.p.m.
less in cutting oils effectively prevent spoilage and offensive odors therein. Generally, the compounds are effective in quantities of the order of about 0.25 to 10,000 p.p.m.
The compounds of the invention may be added directly to the process water in any suitable tank. However, even though lOS8~5~9 the maximum concentrations used are small, the volumes are large and uniform mixing is highly desirable. The most useful mode of addition is to prepare a relatively smaller, but more concen-trated solution than the final dilution desired. This solution can then be metered by a proportioning pump or its equivalent into a suitably agitated tank or flow of water as the latter is being pumped to the point of use. Normal turbulent flow in the conduit produces adequate mixing. In this way, accurate dosages can be supplied and uniform dilutions obtained.
If desired, any of the numerous well known additives may be employed with the compounds provided they are compatible therewith. It may be useful to aid dispersion of a compound by addition of conventional surfactants in order to prepare concentrated suspensions or emulsions, aqueous or nonaqueous, prior to addition to the process water. Suitable dispersions may be prepared by agitating the compounds in the presence of a sur-factant such as sodium lauryl sulfate, aliphatic and aromatic sulfonates, e.g., sulfonated castor oil, or various alkaryl sulfonates, e.g. the sodium salt of mono sulfonated nonyl naphthalene. Non-ionic types of emulsifying agents such as the higher molecular weight alkyl polyglycol ethers and analogous thio ethers such as the decyl, dodecyl and tetradecyl polyglycol ethers and thio ethers containing from about 25 to 75 carbon atoms may be used. The concentration of surfactant in the final emulsion should be sufficient to make the oil and water phases readily dispersible. For purposes of forming a spray emulsion, from about 0.02 to 3~ of the surfactant will be effec-tive. In general, formulations containing a surface active agent in the amount of from 1 to 20~ by weight of active ingredient are satisfactory although such proportion may be varied over a wide range of proportions depending upon the particular ~()581~
circumstance.
Adjuvants such as wetting agents or humectants may, if desired, be employed particularly when compounding an aqueous dispersion. Examples of humectants are glycerine, diethylene glycol, polyethylene glycol and the like.
Sulfate Reducing Bacteria in Vitro Test This test measures the bac~ericidal properties of a compound when in contact with a sulfate reducing bacteria, specifically Desulfovibrio desulfuricans. The test is con-ducted by dissolving the test compound in acetone to give an 0.5~ solution. This toxicant is added to vials containing sterile Sulfate API broth with tryptone under anaerobic con-ditions at such levels to give final toxicant concentrations of 1, 5, 10 and 50 ~g/ml. of solution. An inoculant solution of 0.5 ml. of the growing organism, Desulfovibrio desulfuricans, is added to the vials followed by sufficient sterile distilled water to give a total of 10 ml. of solution in the vials. The vials are incubated at room temperature for 3 to 5 days until untreated controls show growth of the organism as indicated by the black color development in the vials.
The following is a summary of the minimum inhibitory concentration necessary to control the organism.
Compound Minimum Inhibitory Conc ~g/ml 1,3-dichloroacetoneoxime acetate 5 1,3-dichloroacetoneoxime propionate 1*
Compound Number 2 5 *lowest concentration tested ---` io5~99 As can be seen by the test results, the compounds find particular utility as bactericides and fungicides. The compounds can be applied in a variety of ways at various concentrations. They can be combined with suitable carriers and applied as dusts, sprays, or drenches. The amount applied will depend on the nature of the utility. The rate of application can also vary with the microbiological use intended.
The problems associated with sulfate reducing bacteria and method of application for the control thereof are described in U.S. 3,300,375.
Claims (13)
1) A compound of the formula in which R is alkyl having 1 to 6 carbon atoms.
2) The compound of claim 1 in which R is methyl;
3) The compound of claim 1 in which R is ethyl.
4) The compound of claim 1 in which R is n-butyl
5) Method of inhibiting the growth of bacteria which com-prises apply thereto a bactericidally effective amount of a compound of the formula in which R is alkyl having 1 to 6 carbon atoms.
6) A method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of a compound of the formula in which Ris alkyl having 1 to 6 carbon atoms.
7) A method of inhibiting the growth of sulfate reducing bacteria which comprises contacting said bacteria with an effective amount of a compound of the formula in which R is alkyl having 1 to 6 carbon atoms.
8) The method of claim seven in which R is ethyl.
9) The method of claim seven in which said bacteria is of the species Desulfovibrio.
10) A method of inhibiting the growth of sulfate re-ducing bacteria which comprises contacting said bacteria with an effective amount of the compound 1,3-dichloroacetone-oxime acetate or 1,3-dichloroacetoneoxime propionate.
11) The method of claim ten in which said compound is 1,3-dichloroacetoneoxime acetate.
12) The method of claim ten in which said compound is 1,3-dichloroacetoneoxime propionate.
13) The method of claim ten in which said bacteria is of a species Desulfovibrio.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54216075A | 1975-01-20 | 1975-01-20 | |
| US05/542,159 US3988357A (en) | 1975-01-20 | 1975-01-20 | Certain oxime carbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058199A true CA1058199A (en) | 1979-07-10 |
Family
ID=27066933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,710A Expired CA1058199A (en) | 1975-01-20 | 1976-01-16 | Certain oxime carbonates and method of controlling sulfate reducing bacteria |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5195021A (en) |
| AR (1) | AR215427A1 (en) |
| BR (1) | BR7600311A (en) |
| CA (1) | CA1058199A (en) |
| DE (1) | DE2601867A1 (en) |
| DK (1) | DK20876A (en) |
| EG (1) | EG11864A (en) |
| ES (1) | ES444439A1 (en) |
| FR (1) | FR2297841A1 (en) |
| NL (1) | NL7600493A (en) |
| NO (1) | NO141406C (en) |
| NZ (1) | NZ179768A (en) |
| PH (1) | PH11401A (en) |
| PL (1) | PL100802B1 (en) |
| RO (1) | RO77422A (en) |
| SE (1) | SE7600485L (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4740524A (en) * | 1986-05-16 | 1988-04-26 | Rohm And Haas Company | Alpha-halopyruvate oxime |
| JPH01268603A (en) * | 1988-04-21 | 1989-10-26 | Shimizu Corp | Inhibition of growth of sulfuric acid-reducing bacterium |
| DE29821292U1 (en) * | 1998-11-20 | 1999-01-28 | Siemens Ag | High-voltage circuit breaker with two interrupters |
-
1976
- 1976-01-15 NO NO760132A patent/NO141406C/en unknown
- 1976-01-15 FR FR7600934A patent/FR2297841A1/en not_active Withdrawn
- 1976-01-15 PH PH17280A patent/PH11401A/en unknown
- 1976-01-16 CA CA243,710A patent/CA1058199A/en not_active Expired
- 1976-01-16 NZ NZ179768A patent/NZ179768A/en unknown
- 1976-01-16 AR AR261943A patent/AR215427A1/en active
- 1976-01-19 EG EG25/76A patent/EG11864A/en active
- 1976-01-19 SE SE7600485A patent/SE7600485L/en unknown
- 1976-01-19 ES ES444439A patent/ES444439A1/en not_active Expired
- 1976-01-19 NL NL7600493A patent/NL7600493A/en not_active Application Discontinuation
- 1976-01-19 BR BR7600311A patent/BR7600311A/en unknown
- 1976-01-20 PL PL1976186648A patent/PL100802B1/en unknown
- 1976-01-20 DE DE19762601867 patent/DE2601867A1/en active Pending
- 1976-01-20 RO RO7684557A patent/RO77422A/en unknown
- 1976-01-20 JP JP51005376A patent/JPS5195021A/ja active Pending
- 1976-01-20 DK DK20876*#A patent/DK20876A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO760132L (en) | 1976-07-21 |
| AR215427A1 (en) | 1979-10-15 |
| FR2297841A1 (en) | 1976-08-13 |
| DK20876A (en) | 1976-07-21 |
| SE7600485L (en) | 1976-07-21 |
| EG11864A (en) | 1978-06-30 |
| PH11401A (en) | 1977-12-14 |
| RO77422A (en) | 1982-02-26 |
| BR7600311A (en) | 1976-08-31 |
| NO141406C (en) | 1980-03-05 |
| JPS5195021A (en) | 1976-08-20 |
| NL7600493A (en) | 1976-07-22 |
| NZ179768A (en) | 1978-03-06 |
| DE2601867A1 (en) | 1976-07-22 |
| PL100802B1 (en) | 1978-11-30 |
| AU1033376A (en) | 1977-07-21 |
| ES444439A1 (en) | 1977-09-01 |
| NO141406B (en) | 1979-11-26 |
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