US2376650A - Fungicidal and bactericidal compositions - Google Patents
Fungicidal and bactericidal compositions Download PDFInfo
- Publication number
- US2376650A US2376650A US424477A US42447741A US2376650A US 2376650 A US2376650 A US 2376650A US 424477 A US424477 A US 424477A US 42447741 A US42447741 A US 42447741A US 2376650 A US2376650 A US 2376650A
- Authority
- US
- United States
- Prior art keywords
- mixture
- sodium
- parts
- phenolate
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 40
- 230000000844 anti-bacterial effect Effects 0.000 title description 9
- 230000000855 fungicidal effect Effects 0.000 title description 8
- 229940031826 phenolate Drugs 0.000 description 11
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 11
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical class OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 9
- 231100000167 toxic agent Toxicity 0.000 description 8
- 239000003440 toxic substance Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- -1 alkali metal salts Chemical class 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 7
- KPFPEXKMIDAQNO-UHFFFAOYSA-N 3-chloro-2-phenylphenol Chemical compound OC1=CC=CC(Cl)=C1C1=CC=CC=C1 KPFPEXKMIDAQNO-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 150000004707 phenolate Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DSQWWSVOIGUHAE-UHFFFAOYSA-N 4-chloro-2-phenylphenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC=CC=C1 DSQWWSVOIGUHAE-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- SPJMAPNWDLIVRR-UHFFFAOYSA-M sodium;3-chloro-2-phenylphenolate Chemical compound [Na+].[O-]C1=CC=CC(Cl)=C1C1=CC=CC=C1 SPJMAPNWDLIVRR-UHFFFAOYSA-M 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- LMUKIFZFZRTUIY-UHFFFAOYSA-N 5-chloro-2-phenylphenol Chemical compound OC1=CC(Cl)=CC=C1C1=CC=CC=C1 LMUKIFZFZRTUIY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001289435 Astragalus brachycalyx Species 0.000 description 1
- 235000002917 Fraxinus ornus Nutrition 0.000 description 1
- 241001492300 Gloeophyllum trabeum Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-M pentachlorophenolate Chemical compound [O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- YBXNXQNSYXJDAZ-UHFFFAOYSA-M sodium;2,3,4,5-tetrachlorophenolate Chemical compound [Na+].[O-]C1=CC(Cl)=C(Cl)C(Cl)=C1Cl YBXNXQNSYXJDAZ-UHFFFAOYSA-M 0.000 description 1
- YLFFQZKUOUYUFG-UHFFFAOYSA-M sodium;2,3,4,6-tetrachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C=C(Cl)C(Cl)=C1Cl YLFFQZKUOUYUFG-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Definitions
- the present invention is concerned with fungi cidal and bactericidal compositions and particu larly with such compositions comprising as an active toxicant a mixture of phenolates.
- compositions are ob.- tained which exert a fungicidal and bactericidal action greatly in excess of that predictable from a knowledge of the eflectiveness of the component phenolates.
- the proportions of materials employed vary somewhat with the use for which the composition is designed and the particular salts concerned. Generally, from ill to 100 parts byweight of the alkali metal salt of Z-phenyimonochloro-phenol is used for each 100 parts of the alkali metal pentachlorophenolate.
- compositions of the invention may be prepared by grinding or otherwise mixing the 2- phenyl-monochlorophenolate and pentachlorophenolate'to obtain finely-divided solid products adapted to be dissolved in water or other suitable liquid carrier.; In an alternate procedure; a mixture oi the free phenols may be treated with aeous alkali to form liquid phenolate products adapted to be either evaporated to dryness and around, or employed for a fungicidal and germicidal control as obtained or after modification with additional liquid diluent.
- phenolate mixtures have been found" superior to either the pentachlorophenolates or 42-phenyl-monochlorophenolates alone as regards the fungicidal and bactericidal controls accom-' plished in such representative fields as the treatment .of freshly sawn lumber for sap stain control, mold-proofing of canvas and other rough fabrics, preservation of cordage, etc, In such operations aqueous solutions comprising from.
- the treatment also serves to protectthe cellulosic structure irom'attack by termites.
- the pheno'late mixtures have been found effective in the preservation of paper and specifically in the mold proofing oi egg case flats and fillers.
- lrornabout Otto 0.5 per cent by weight on a dry basis of the phenolate mixture is incorporated with the paper pulp dur ing the beating step.
- the paper product made from the treated pulp is resistant to mold growth even under conditions of high humidity, and as in the case oi egg flats and fillers, may exert a desirable iungistatic eiiect upon food products wrapped or packed therein.
- composition oi the present invention has been found particularly effective is that of slime and algae control. From 2 to 10 parts of the phenoiate mixture per. million parts of water prevents the growth oi algae and slime organisms in the water systems oi paper mills humidifier and boiler installations, cooling towers, etc. In such application a mixture of 60 per cent by weight pentachlorophenolate-dll per cent by weight fi-phenyl- A series of determinations were carried out to ascertain the eii'ectiveness of a mixture of sodium pentachlorophenolate and sodium 2 phenylmonochloro-phenolate (the ortho-para mixture) against a number of representative organisms.
- the particular product employed consisted of a mechanical mixture of 80 parts-by weight oi the sodium pentachlorophenolate with 40 parts by weight of the 2-phenyi-monochloro-phenolate. Control determinations were made with sodium -pentachlorophenolate alone. The following table sets forth the results obtained in terms of parts by weight of tomcant per million parts of water required to kill the test organisms employed.
- the phenolate mixture was found to completely inhibit and kill C. pillijera at a concentration of between 0.0035 and 0.005 per cent by weight.
- Sodium pentachlorophenolate inhibited and killed this organism at a concentration of between 0.005 and 0.007 per cent.
- the phenolate mixture gave complete inhibition and kill at between 0.0025 and 0.010 per cent.
- sodium pentadispersing agents for example, inorganic and organic mercurials, 'borax, dinitrophenols and their salts, and water-soluble salts of sulfuric acid derivatives of alcohols, phenols, aromatic hydrocarbons, etc. may be incorporated into the phenolate mixtures, if desired, provided only that such addition agents not enter into chemical reaction with the phenol salts.
- a flmgicidal and bactericidal composition comprising as an active toxicant a mixture oi! the alkali metal salts of pentachlorophenol and of 2- phenyl monochlorophenol.
- a fungicidal and bactericidal composition comprising as an active toxicant a mixture of from 10 to 100 parts by weight oi sodium 2-phenylmonochloro-phenolate with 100 parts of sodium pen tachlorophenolate.
- chlorophenoiate between 0.010 and 0.020 per cent was required to give inhibition of growth, and between 0.020 and 0.035 per cent to kill the orenism.
- the phenola'te mixture gave total inhibition and hill at a concentration of between 0.001 and 0.002 per cent.
- concentration required to give total inhibition was between 0.002 and 0.0030.
- a concentration of between 0.0035 and 0.005" was required to kill the organism with the sodium pentachlorophenolate alone.
- compositions as hereinbefore described comprise the mixture of phenolates as the principal active toxicant but may be modified by the addition of other toxicants, or wetting and 3.
- a fimgicidal and bactericidal composition comprising as an active toxicant a mixture of from 10 to 100 parts hyweight of an alkali metal salt of 2-phenyl-monochlorophenol with 100 parts by weight of an alkali metal salt of pentachlorophenoL 4.
- a fungicidal and bactericidal composition comprising as an active tomcant a mixture of from 10 to 100 parts by weight of sodium 2- phenyi-monochloro-phenolate with 100 parts by weight of a mixture of sodium pentachlorophenolate and sodium tetrachlorophenolate.
- a fungicidal and bactericidal composition comprising as an active toxicant a mixture of 00 parts by weight of sodium pentachlorophenolate and parts of sodium 2-p-henyl-monochlorophenolate.
Description
Patented May 1945 moron). AND BACTEBJUIDAL comosrrross with x. Bellman, manna, Mich, assignoi' to The Dow Chemical Company, Midland, Mich, a corporation of Michigan No Drawing. Application December 28, liiil', Serial No. 424,477
Claims.
The present invention is concerned with fungi cidal and bactericidal compositions and particu larly with such compositions comprising as an active toxicant a mixture of phenolates.
According to the present invention, it has been discovered that when alkali metal salts of pentachlorophenol and of 2 phenyl-monochlorophenol are mixed together, compositions are ob.- tained which exert a fungicidal and bactericidal action greatly in excess of that predictable from a knowledge of the eflectiveness of the component phenolates. The proportions of materials employed vary somewhat with the use for which the composition is designed and the particular salts concerned. Generally, from ill to 100 parts byweight of the alkali metal salt of Z-phenyimonochloro-phenol is used for each 100 parts of the alkali metal pentachlorophenolate.
The compositions of the invention may be prepared by grinding or otherwise mixing the 2- phenyl-monochlorophenolate and pentachlorophenolate'to obtain finely-divided solid products adapted to be dissolved in water or other suitable liquid carrier.; In an alternate procedure; a mixture oi the free phenols may be treated with aeous alkali to form liquid phenolate products adapted to be either evaporated to dryness and around, or employed for a fungicidal and germicidal control as obtained or after modification with additional liquid diluent.
Mixtures of the sodium salts of pentachlorophenol and of 2-phenyl-monochloro-phenol constltute the preferred embodiment of the present invention, although other salts such as the potassium and lithium salts or mixtures of sodium. potassium, and lithium salts may be substituted therefor. The commonest form in which the 2- phenyl mono-chloro-phenolate is employed is as a mixture comprising from '10 to 80 per cent by weight of the ortho-chloro isomer and the bal ance principally the para-chloro isomer. with only'a trace of the meta-chloro compound. This mixture is obtained by forming the alkali metal phenolate from the phenol mixture resulting from the direct chlorination of -2-phenyl-phenol.
If desired, however, pure z-phenyl-fi-chloro .phenolate, 2-phenyl-5-chloro-phenolate, or 2- phenyl-4-chloro-phenolate may beemployed.
The phenolate mixtures have been found" superior to either the pentachlorophenolates or 42-phenyl-monochlorophenolates alone as regards the fungicidal and bactericidal controls accom-' plished in such representative fields as the treatment .of freshly sawn lumber for sap stain control, mold-proofing of canvas and other rough fabrics, preservation of cordage, etc, In such operations aqueous solutions comprising from.
about 4 to about pounds .of to'xicant per 100 gallons (U. S.) are employed. The treatment of a complished eitherby dipping or by pressure impre'gnation; In pressure impregnation of wood.
the treatment also serves to protectthe cellulosic structure irom'attack by termites.
5 Similarly,. the pheno'late mixtures have been found effective in the preservation of paper and specifically in the mold proofing oi egg case flats and fillers. For this use lrornabout Otto 0.5 per cent by weight on a dry basis of the phenolate mixture is incorporated with the paper pulp dur ing the beating step. The paper product made from the treated pulp is resistant to mold growth even under conditions of high humidity, and as in the case oi egg flats and fillers, may exert a desirable iungistatic eiiect upon food products wrapped or packed therein.
A iurther development in which the composition oi the present invention has been found particularly effective is that of slime and algae control. From 2 to 10 parts of the phenoiate mixture per. million parts of water prevents the growth oi algae and slime organisms in the water systems oi paper mills humidifier and boiler installations, cooling towers, etc. In such application a mixture of 60 per cent by weight pentachlorophenolate-dll per cent by weight fi-phenyl- A series of determinations were carried out to ascertain the eii'ectiveness of a mixture of sodium pentachlorophenolate and sodium 2 phenylmonochloro-phenolate (the ortho-para mixture) against a number of representative organisms.
The particular product employed consisted of a mechanical mixture of 80 parts-by weight oi the sodium pentachlorophenolate with 40 parts by weight of the 2-phenyi-monochloro-phenolate. Control determinations were made with sodium -pentachlorophenolate alone. The following table sets forth the results obtained in terms of parts by weight of tomcant per million parts of water required to kill the test organisms employed.
. Partspermilliontokill with- Organism Muted phenolates Bumble 2 A mixture, of 40 parts by weight or sodium 2- .phenyl-monochloro-phenolate and 30 parts 01 sodium pentachlorophenolate was modified by the inclusion of 30 parts by weight of sodium 2.3.4.6- tetrachlorophenolate. This mixture or toxicant materials was tested according to the well known agar plate method to determine its efficiency against such common wood stainers and destroyera as C. pillifera, H. gelattnosum, and L. trabea. Sodium pentachlorophenolate alone was employed as a control material.
The phenolate mixture was found to completely inhibit and kill C. pillijera at a concentration of between 0.0035 and 0.005 per cent by weight. Sodium pentachlorophenolate inhibited and killed this organism at a concentration of between 0.005 and 0.007 per cent.
Against H. geiatmosum, the phenolate mixture gave complete inhibition and kill at between 0.0025 and 0.010 per cent. With sodium pentadispersing agents. For example, inorganic and organic mercurials, 'borax, dinitrophenols and their salts, and water-soluble salts of sulfuric acid derivatives of alcohols, phenols, aromatic hydrocarbons, etc. may be incorporated into the phenolate mixtures, if desired, provided only that such addition agents not enter into chemical reaction with the phenol salts.
I claimi 1. A flmgicidal and bactericidal composition comprising as an active toxicant a mixture oi! the alkali metal salts of pentachlorophenol and of 2- phenyl monochlorophenol.
2. A fungicidal and bactericidal composition comprising as an active toxicant a mixture of from 10 to 100 parts by weight oi sodium 2-phenylmonochloro-phenolate with 100 parts of sodium pen tachlorophenolate.
chlorophenoiate, between 0.010 and 0.020 per cent was required to give inhibition of growth, and between 0.020 and 0.035 per cent to kill the orenism.
Against L. trclrea, the phenola'te mixture gave total inhibition and hill at a concentration of between 0.001 and 0.002 per cent. With sodium pentachlorophenolate, the concentration required to give total inhibition was between 0.002 and 0.0030. A concentration of between 0.0035 and 0.005" was required to kill the organism with the sodium pentachlorophenolate alone.
The compositions as hereinbefore described comprise the mixture of phenolates as the principal active toxicant but may be modified by the addition of other toxicants, or wetting and 3. A fimgicidal and bactericidal composition comprising as an active toxicant a mixture of from 10 to 100 parts hyweight of an alkali metal salt of 2-phenyl-monochlorophenol with 100 parts by weight of an alkali metal salt of pentachlorophenoL 4. a fungicidal and bactericidal composition comprising as an active tomcant a mixture of from 10 to 100 parts by weight of sodium 2- phenyi-monochloro-phenolate with 100 parts by weight of a mixture of sodium pentachlorophenolate and sodium tetrachlorophenolate.
5. A fungicidal and bactericidal composition comprising as an active toxicant a mixture of 00 parts by weight of sodium pentachlorophenolate and parts of sodium 2-p-henyl-monochlorophenolate.
DONALD K. BAILMAN.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US424477A US2376650A (en) | 1941-12-26 | 1941-12-26 | Fungicidal and bactericidal compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US424477A US2376650A (en) | 1941-12-26 | 1941-12-26 | Fungicidal and bactericidal compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2376650A true US2376650A (en) | 1945-05-22 |
Family
ID=23682760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US424477A Expired - Lifetime US2376650A (en) | 1941-12-26 | 1941-12-26 | Fungicidal and bactericidal compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2376650A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965535A (en) * | 1955-12-05 | 1960-12-20 | Monsanto Chemicals | Pentachlorobenzenesulfenyl chloride |
| US3063895A (en) * | 1959-01-29 | 1962-11-13 | William Pearson Ltd | Disinfectant compositions |
-
1941
- 1941-12-26 US US424477A patent/US2376650A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965535A (en) * | 1955-12-05 | 1960-12-20 | Monsanto Chemicals | Pentachlorobenzenesulfenyl chloride |
| US3063895A (en) * | 1959-01-29 | 1962-11-13 | William Pearson Ltd | Disinfectant compositions |
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