US3193451A - Fungicidal composition of undecylenic acid derivatives - Google Patents
Fungicidal composition of undecylenic acid derivatives Download PDFInfo
- Publication number
- US3193451A US3193451A US87123A US8712361A US3193451A US 3193451 A US3193451 A US 3193451A US 87123 A US87123 A US 87123A US 8712361 A US8712361 A US 8712361A US 3193451 A US3193451 A US 3193451A
- Authority
- US
- United States
- Prior art keywords
- undecylenic acid
- parts
- acid derivatives
- fungicidal composition
- undecylenic
- 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
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N Undecylenic acid Chemical group OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 title description 26
- 230000000855 fungicidal Effects 0.000 title description 10
- 239000000203 mixture Substances 0.000 title description 8
- 244000005700 microbiome Species 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000344 soap Substances 0.000 description 20
- 229960002703 undecylenic acid Drugs 0.000 description 20
- 241000894006 Bacteria Species 0.000 description 10
- 241000233866 Fungi Species 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- 239000006071 cream Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
- 210000003491 Skin Anatomy 0.000 description 8
- 229940043237 diethanolamine Drugs 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000002070 germicidal Effects 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-hydroxypropyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 2
- OLFMBPYPRDPNQA-UHFFFAOYSA-N ClC1=C(C(C(C=C1)(C)O)Cl)C Chemical compound ClC1=C(C(C(C=C1)(C)O)Cl)C OLFMBPYPRDPNQA-UHFFFAOYSA-N 0.000 description 2
- ISTASGAHDLTQRU-UHFFFAOYSA-N N-(2-hydroxyethyl)undec-10-enamide Chemical compound OCCNC(=O)CCCCCCCCC=C ISTASGAHDLTQRU-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 208000006641 Skin Disease Diseases 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M Sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 239000008294 cold cream Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 201000009910 diseases by infectious agent Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000116 mitigating Effects 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000002335 preservative Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229940093625 propylene glycol monostearate Drugs 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
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
- 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
- A01N37/20—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 containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
Definitions
- amidic derivatives of undecylenic acid described and claimed hereinafter have fungicidal effects and that these amidic derivatives are active not only against fungi but also against bacteria and other microorganisms.
- these undecylenic acid derivatives are of W efIect against gram negative bacteria but are rather effective against many gram positive organisms. They are also effective against many molds and yeasts and against many fungi.
- the undecylenic acid derivatives used in this invention show consider-able advantages over the undecylenic acid monoethanolamide, either because in some cases their etiectivness is greater and may embrace a greater range of organisms, or because in other cases the product possesses characteristics which make it more convenient in use, as for example, greater solubility in water.
- the present invention relates to a process for inhibiting the growth of microorganisms, killing microorganisms and for the relief and treatment of diseases resulting from the action of microorganisms, comprising the use for said purposes of undecylenic acid derivatives corresponding to the general formula CmHmC O.N.(CHz) (CHzO) yH wherein the group C ,,H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms; n stands for an integer of 1-4 and y is an integer in the range of 1-30.
- the scope of the present invention includes compounds as defined above when these are associated with excess alkylolarnine in the form of such a complex. Indeed, since these complexes are often more soluble in water than the pure amide they may very well be useful for incorporation in aqueous compositions.
- An example of such a material is the product obtained by condensing undecylenic acid with diethanolamine in the proportion of 1 gram molecule of the former to 2 gram molecules of the latter at 150 to 170 C.
- the products of this invention may also be incorporated in dusting powders or may be applied to the skin in some cases as solutions in an organic solvent, for example, ethyl alcohol. They may be incorporated in creams or lotions in which other materials commonly used in cosmetics or pharmacy are also present. They may also be incorporated in compositions based mainly on wax, oil or grease, for example, lipstick, brilliantines or water-in-oil emulsions such as cold cream or some types of hair cream.
- the amides may also be incorporated in shampoos or detergent preparations intended to cleanse the hair or skin. They may also be incorporated in soap preparations including the conventional bars or tablets, liquid soaps, shaving creams, and the like.
- amidic derivatives described shall be used for cosmetic or pharmaceutical purposes, it will be appreciated that they may be incorporated in a wide range of preparations not necessarily cosmetic or pharmaceutical, where a germicidal or fungicidal action is desired. They may further be incorporated in preparations not intended to act as fungicides or germicides but where a preservative is required to prevent spoilage through microorganisms.
- Example 1 A lotion was prepared by dissolving in parts of water 5 parts of a product obtained by reacting 1 gram molecule of undecylenic acid with 2 gram molecules of diethanol-amine at C. to C. till the free fatty acid content fell to about 5%. This lotion was suitable for treating skin conditions caused by fungi.
- Example 2 Three parts of undecylenic monoisopropanolamide were dissolved in ten parts of isopropyl alcohol at about 30 C. and sprayed onto 97 parts of cosmetic grade talc. The whole was intimately mixed and kept warm during the mixing operation so as to volatilise as much as possible of the alcohol. The resulting powder was suitable as a foot powder for treating conditions such as atheletes foot.
- Example 3 Three parts of undecylenic acid monoisopropanolamide are stirred into 92.5 parts of water at 65 C. together with 4.5 parts of sodium N-lauroyl sarcosinate which acts as a dispersing agent. When cool, the resulting product constitutes a very fine dispersion of undecylenic acid monoisopropanolamide which, when first made, is almost transparent. This dispersion can be used for the treatment of skin conditions caused by bacteria or fungi.
- Example 4 2 parts of undecylenic acid n-propanolamide, in the form of fine flakes, are added to 97.5 parts of toilet soap flakes on a triple roller soap mill.
- the soap is a product made from tallow and coconut oil.
- 0.5 part of a soap perfume having a rose odor is also added.
- the whole is milled and then fed back into the mill to pass through again and again until the undecylenic n-propanolamide is uniformly dispersed. Four millings in all were adequate.
- the resulting soap was fed into a soap plodder, extruded, cut and finally stamped as toilet soap tablets in accordance with the usual techniques.
- the resultant toilet soap has germicidal and fungacidal powers and can be used for preventing or mitigation of skin diseases caused by infection.
- Example 5 0.1 part of dichlormetaxylenol together with 2 parts of undecylenic acid monoisopropanolamide are dissolved in 20 parts of propylene glycol monostearate and 5 parts of stearic acid are added, all at 70 C. The whole is poured into 70.9 parts of water together with 2 parts of triethanolamine, all at 55 C. The mixture is vigorously stirred and then cooled with stirring to 25 C. The resulting product is a nearly white cream. This cream is efiective against a very wide range of micro- The efiectiveness of. the undecylenic derivaorganisms. v tive against fungi is supplemented by the etfectiveness of the dichlometaxylenol against bacteria, particularly against gram negative bacteria against which the undecylenic product is less effective.
- a process for combatting micro-organisms which comprises applying thereto a biocidally effective amount wherein the group C H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms;;n stands'for an integer of'14 and y is an integer in the range of 1-30.
- a process for c'ombatting micro-organisms which comprises applying thereto a biocidally efiective amount of a compound:
Description
United States Patent 2 Claims. (51. 167-22) It has been known previously that the monoethanolamide of undecylenic acid has a fungicidal effect and it has been proposed to use this monoethanolamide derivative as a fungicidal agent.
It has now been discovered that certain other amidic derivatives of undecylenic acid described and claimed hereinafter have fungicidal effects and that these amidic derivatives are active not only against fungi but also against bacteria and other microorganisms.
In general these undecylenic acid derivatives are of W efIect against gram negative bacteria but are rather effective against many gram positive organisms. They are also effective against many molds and yeasts and against many fungi.
The undecylenic acid derivatives used in this invention show consider-able advantages over the undecylenic acid monoethanolamide, either because in some cases their etiectivness is greater and may embrace a greater range of organisms, or because in other cases the product possesses characteristics which make it more convenient in use, as for example, greater solubility in water.
The present invention relates to a process for inhibiting the growth of microorganisms, killing microorganisms and for the relief and treatment of diseases resulting from the action of microorganisms, comprising the use for said purposes of undecylenic acid derivatives corresponding to the general formula CmHmC O.N.(CHz) (CHzO) yH wherein the group C ,,H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms; n stands for an integer of 1-4 and y is an integer in the range of 1-30.
The scope of the present invention includes compounds as defined above when these are associated with excess alkylolarnine in the form of such a complex. Indeed, since these complexes are often more soluble in water than the pure amide they may very well be useful for incorporation in aqueous compositions. An example of such a material is the product obtained by condensing undecylenic acid with diethanolamine in the proportion of 1 gram molecule of the former to 2 gram molecules of the latter at 150 to 170 C.
The products of this invention may also be incorporated in dusting powders or may be applied to the skin in some cases as solutions in an organic solvent, for example, ethyl alcohol. They may be incorporated in creams or lotions in which other materials commonly used in cosmetics or pharmacy are also present. They may also be incorporated in compositions based mainly on wax, oil or grease, for example, lipstick, brilliantines or water-in-oil emulsions such as cold cream or some types of hair cream. The amides may also be incorporated in shampoos or detergent preparations intended to cleanse the hair or skin. They may also be incorporated in soap preparations including the conventional bars or tablets, liquid soaps, shaving creams, and the like. While it is primarily intended that the amidic derivatives described shall be used for cosmetic or pharmaceutical purposes, it will be appreciated that they may be incorporated in a wide range of preparations not necessarily cosmetic or pharmaceutical, where a germicidal or fungicidal action is desired. They may further be incorporated in preparations not intended to act as fungicides or germicides but where a preservative is required to prevent spoilage through microorganisms.
While it is intended that the compounds described above should be able to be used alone, their use together with other materials known to those skilled in the art to be active against microorganisms is not excluded.
The following example illustrates some specific embodiment of and best modes for carrying out the invention, to which the invention is not limited. All parts are by weight.
Example 1 A lotion was prepared by dissolving in parts of water 5 parts of a product obtained by reacting 1 gram molecule of undecylenic acid with 2 gram molecules of diethanol-amine at C. to C. till the free fatty acid content fell to about 5%. This lotion was suitable for treating skin conditions caused by fungi.
Example 2 Three parts of undecylenic monoisopropanolamide were dissolved in ten parts of isopropyl alcohol at about 30 C. and sprayed onto 97 parts of cosmetic grade talc. The whole was intimately mixed and kept warm during the mixing operation so as to volatilise as much as possible of the alcohol. The resulting powder was suitable as a foot powder for treating conditions such as atheletes foot.
Example 3 Three parts of undecylenic acid monoisopropanolamide are stirred into 92.5 parts of water at 65 C. together with 4.5 parts of sodium N-lauroyl sarcosinate which acts as a dispersing agent. When cool, the resulting product constitutes a very fine dispersion of undecylenic acid monoisopropanolamide which, when first made, is almost transparent. This dispersion can be used for the treatment of skin conditions caused by bacteria or fungi.
Example 4 2 parts of undecylenic acid n-propanolamide, in the form of fine flakes, are added to 97.5 parts of toilet soap flakes on a triple roller soap mill. The soap is a product made from tallow and coconut oil. 0.5 part of a soap perfume having a rose odor is also added. The whole is milled and then fed back into the mill to pass through again and again until the undecylenic n-propanolamide is uniformly dispersed. Four millings in all were adequate. The resulting soap was fed into a soap plodder, extruded, cut and finally stamped as toilet soap tablets in accordance with the usual techniques. The resultant toilet soap has germicidal and fungacidal powers and can be used for preventing or mitigation of skin diseases caused by infection.
Example 5 0.1 part of dichlormetaxylenol together with 2 parts of undecylenic acid monoisopropanolamide are dissolved in 20 parts of propylene glycol monostearate and 5 parts of stearic acid are added, all at 70 C. The whole is poured into 70.9 parts of water together with 2 parts of triethanolamine, all at 55 C. The mixture is vigorously stirred and then cooled with stirring to 25 C. The resulting product is a nearly white cream. This cream is efiective against a very wide range of micro- The efiectiveness of. the undecylenic derivaorganisms. v tive against fungi is supplemented by the etfectiveness of the dichlometaxylenol against bacteria, particularly against gram negative bacteria against which the undecylenic product is less effective.
Whatis claimed is: v
1. A process for combatting micro-organisms, which comprises applying thereto a biocidally effective amount wherein the group C H CO is the acyl derivative of undecylenic acid, R is selected from the group consisting of alkyl and alkylol, and containing up to 4 carbon atoms;;n stands'for an integer of'14 and y is an integer in the range of 1-30.
2. A process for c'ombatting micro-organisms, which comprises applying thereto a biocidally efiective amount of a compound:
* CH CH OH CmHieC ON CHg.CHz.OH
admixed with excess diethanolamine such thatthere is present an excess of diethanolamine about equal to the amount combined in the undecylenic acid diethanolamide.
September 1945, pp. 415425, esp. p. 422.
Broder'sen et al.: Acta Pharmacologica et Toxicologica, vol. 3 (1947) pp. 17-29.
Reinisch at al.:v J. Soc. Cosmetic Chemists, 5: 3, Nov. 1954, pp. 169478;
Claims (1)
- 2. A PROCESS FOR COMBATING MICRO-ORGANISMS, WHICH COMPRISES APPLYING THERETO A BIOCIDALLY EFFECTIVE AMOUNT OF A COMPOUND:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3193451A true US3193451A (en) | 1965-07-06 |
Family
ID=2939683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US87123A Expired - Lifetime US3193451A (en) | 1961-02-06 | Fungicidal composition of undecylenic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3193451A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392600A1 (en) * | 1977-05-31 | 1978-12-29 | Block Drug Co | INSECTICIDES BASED ON ALKANOLAMIDES |
| US4325973A (en) * | 1977-01-12 | 1982-04-20 | Gaf Corporation | Hydroxyalkyl amides as fungicides to eumycotina in phanerogamia plant life |
| WO1996035767A1 (en) * | 1995-05-10 | 1996-11-14 | Elf Atochem S.A. | Bacteriostatic compositions and use in metal working fluids |
| US6103768A (en) * | 1991-05-01 | 2000-08-15 | Mycogen Corporation | Fatty acid based compositions and methods for the control of plant infections and pests |
| EP1161223A1 (en) * | 1999-03-02 | 2001-12-12 | Shaw Mudge & Company | Fragrance and flavor compositions containing odor neutralizing agents |
| US6495097B1 (en) | 1999-03-02 | 2002-12-17 | Shaw Mildge & Company | Fragrance and flavor compositions containing odor neutralizing agents |
| US20130101530A1 (en) * | 2011-10-25 | 2013-04-25 | Galaxy Surfactants Ltd. | Antimicrobial preservative compositions for personal care products |
| US8871280B1 (en) * | 2011-09-12 | 2014-10-28 | The United States Of America, As Represented By The Secretary Of Agriculture | Compositions and methods for treating fungal activity in plants or soil |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1065984B (en) * | 1957-12-12 | 1959-09-24 | Dreiturm Seifenindustrie G M B | Fungicidal skin care and shampoo products |
-
1961
- 1961-02-06 US US87123A patent/US3193451A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1065984B (en) * | 1957-12-12 | 1959-09-24 | Dreiturm Seifenindustrie G M B | Fungicidal skin care and shampoo products |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325973A (en) * | 1977-01-12 | 1982-04-20 | Gaf Corporation | Hydroxyalkyl amides as fungicides to eumycotina in phanerogamia plant life |
| FR2392600A1 (en) * | 1977-05-31 | 1978-12-29 | Block Drug Co | INSECTICIDES BASED ON ALKANOLAMIDES |
| US6103768A (en) * | 1991-05-01 | 2000-08-15 | Mycogen Corporation | Fatty acid based compositions and methods for the control of plant infections and pests |
| WO1996035767A1 (en) * | 1995-05-10 | 1996-11-14 | Elf Atochem S.A. | Bacteriostatic compositions and use in metal working fluids |
| AU701305B2 (en) * | 1995-05-10 | 1999-01-28 | Elf Atochem S.A. | Bacteriostatic compositions and use in metal working fluids |
| EP1161223A1 (en) * | 1999-03-02 | 2001-12-12 | Shaw Mudge & Company | Fragrance and flavor compositions containing odor neutralizing agents |
| EP1161223A4 (en) * | 1999-03-02 | 2002-07-24 | Shaw Mudge & Company | Fragrance and flavor compositions containing odor neutralizing agents |
| US6495097B1 (en) | 1999-03-02 | 2002-12-17 | Shaw Mildge & Company | Fragrance and flavor compositions containing odor neutralizing agents |
| US8871280B1 (en) * | 2011-09-12 | 2014-10-28 | The United States Of America, As Represented By The Secretary Of Agriculture | Compositions and methods for treating fungal activity in plants or soil |
| US20130101530A1 (en) * | 2011-10-25 | 2013-04-25 | Galaxy Surfactants Ltd. | Antimicrobial preservative compositions for personal care products |
| US9661847B2 (en) | 2011-11-25 | 2017-05-30 | Galaxy Surfactants Ltd. | Antimicrobial preservative compositions for personal care products |
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