US3243342A - Germicidal compositions containing halogenated anilides of thiophene carboxylic acids - Google Patents
Germicidal compositions containing halogenated anilides of thiophene carboxylic acids Download PDFInfo
- Publication number
- US3243342A US3243342A US347007A US34700764A US3243342A US 3243342 A US3243342 A US 3243342A US 347007 A US347007 A US 347007A US 34700764 A US34700764 A US 34700764A US 3243342 A US3243342 A US 3243342A
- Authority
- US
- United States
- Prior art keywords
- carboxylic acids
- compositions containing
- germicidal
- thiophene carboxylic
- containing halogenated
- 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
- 230000002070 germicidal effect Effects 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 title description 15
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 title description 4
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title description 3
- 150000003931 anilides Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 239000000344 soap Substances 0.000 description 11
- 239000003599 detergent Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 7
- -1 thiophene carbox-ylic acids Chemical class 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical class [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Classifications
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- This invention deals with germicidal compositions containing halogenated anilides of thiophene carboxylic acids; More specifically, it relates to germicidal compositions containing compounds having the following generic formula:
- a H Q -t l wherein X is a halogen atom selected from the class consisting of chlorine, bromine, and iodine, A is an atom selected from the class consisting of oxygen and sulfur, a is a numeral from 0 to 2, and b is a numeral from 1 to 3.
- the germicidal compounds of the present invention may be prepared in accordance with the method outlined by Hopper, MacGregor and Wilson in the January 1941 issue of the Journal of the Society of Dyers and Colourists, page 6. Further details for the preparation of the compounds described herein may be found in the article by Hopper, MacGregor and Wilson, Journal Society of Dyers and Colourists, 1939, 55, 450.
- the procedure for preparing arylamides of 2-hydroxy-3-naphthoic acid is followed, with the exception that the corresponding acid and amine of the desired compound, in the molal quantities required, are substituted.
- 2-thiophene carboxylic acid and p-chloroaniline For example, to prepare compound No. 1 of Table I herein, one would use 2-thiophene carboxylic acid and p-chloroaniline.
- Table I lists a number of compounds prepared in accordance with the present invention, and gives their germicidal effectiveness against S. aureus in agar test plates, as millimeters of zone
- compositions comprising a germicidally inert material, i.e., relatively speaking.
- some soaps and detergents possess a bactericidal action, but such action, relative to those of the compounds of the present invention, is weak and of little effect in comparison with the overall germicidal activity of the composition.
- the compounds of the present invention maybe employedinconcentrations as low as 10 ppm, although, from a practical point of view, it is desirable to use as much as 50 ppm, or 0.001% by weight, or 0.01%, and as much as 0.1%, or more.
- germicidal activity includes inhibiting and killing action against bacteria, fungi and similar organisms.
- compositions of. the. present. invention are those comprising soaps and detergents, and especially toilet soaps or cosmetic detergents in which the compounds of the present invention may be employed in concentrations of 0.1% to 0.5% by'weight, or even as much as 1% or more.
- detergent employed herein will be used toinclude all synthetic and natural cleansing compositions, including cationic detergents, such as dimethyl stearamido-propyl-2hydroxy-ammonium dihydrogen phosphate, anionic detergents such as commercial soaps, e.g., alkali metal soaps of hydrolyzed natural or synthetic glycerides of fatty and similar organic acids, e.g., sodium and potassium stearates or oleates, ampholytic detergents, such as sarcosine, non-ionic detergents such as polyoxypropylene polyoxyethylene condensates, natural detergents, such as starches, vegetable gums, and the like, and mixtures thereof.
- soap employed herein is used in its popular or ordinary meaning, i.e., a cleansing composition prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.
- One valuable use of the compounds of the present invention is the use thereof to sanitize fibrous material such as cotton gauze, dressings, textiles, paper pulp, and the like. They also serve as antiseptic agents when incorporated in plastic or rubber compositions, prior to molding into articles of commerce, such as baby rattles, gloves, food wrappers and the like.
- a method of obtaining germicidal activity against Staphylococcus aureus and other bacteria, fungi ,and similar micro-organisms comprising, i
- a is a numeral from 0 to 2
- b is a numeral from 1 to 3.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
United States Patent 3,243,342 GERMICIDAL COMPOSITIONS CONTAINING HALOGENATED ANILIDES OF THIOPHENE CARBOXYLIC ACIDS Herbert C. Stecker, Ho-Ho-Kus, NJ. No Drawing. Filed Feb. 24, 1964, Ser. No. 347,007 '7 Claims. (Cl. 16733) This application is a-continuation-in-pa1t of copending application Serial No. 328,105, filed on December 4, 1963, by Herbert C. Stecker, now abandoned.
This invention deals with germicidal compositions containing halogenated anilides of thiophene carboxylic acids; More specifically, it relates to germicidal compositions containing compounds having the following generic formula:
A H Q -t l wherein X is a halogen atom selected from the class consisting of chlorine, bromine, and iodine, A is an atom selected from the class consisting of oxygen and sulfur, a is a numeral from 0 to 2, and b is a numeral from 1 to 3.
Condensation products of some carboxylic acids and halogenated anilines have been known to possess some dyeing characteristics, but none of .the compounds have been considered to have suificientgermicidal potency to justify commercial consideration.
It has now been discovered that the amide condensation products of thiophene carbox-ylic acids and thio acids with halogenated anilines show high germicidal potency.
The germicidal compounds of the present invention may be prepared in accordance with the method outlined by Hopper, MacGregor and Wilson in the January 1941 issue of the Journal of the Society of Dyers and Colourists, page 6. Further details for the preparation of the compounds described herein may be found in the article by Hopper, MacGregor and Wilson, Journal Society of Dyers and Colourists, 1939, 55, 450. The procedure for preparing arylamides of 2-hydroxy-3-naphthoic acid is followed, with the exception that the corresponding acid and amine of the desired compound, in the molal quantities required, are substituted. For example, to prepare compound No. 1 of Table I herein, one would use 2-thiophene carboxylic acid and p-chloroaniline. Table I lists a number of compounds prepared in accordance with the present invention, and gives their germicidal effectiveness against S. aureus in agar test plates, as millimeters of zone of inhibition. The tests were carried out in triplicate as follows:
Bacteriological tests were performed against Staphylococcus aureus with a 24-hour culture at 37 C. Each of the compounds in Table I was incorporated in soap of Ivory brand (a neutral white high grade toilet soap consisting of a mixture of 80% sodium soap and 20% potassium soap produced from a 70% tallow and 30% coconut oil glyceride blend, in accordance with US. Patent 2,295,594), in 1% by weight concentration of soap and 0.1% of the compound listed. Cotton disks of mm. diameter were steeped in this mixture, thoroughly rinsed, dried, and applied to seeded agar in Petri dishes, and the zones of inhibition were read after 24 hours, the average data being reported in Table I.
These compounds of the present invention are useful in compositions comprising a germicidally inert material, i.e., relatively speaking. For example, some soaps and detergents possess a bactericidal action, but such action, relative to those of the compounds of the present invention, is weak and of little effect in comparison with the overall germicidal activity of the composition. In such Ice compositions, the compounds of the present invention maybe employedinconcentrations as low as 10 ppm, although, from a practical point of view, it is desirable to use as much as 50 ppm, or 0.001% by weight, or 0.01%, and as much as 0.1%, or more. The term germicidal: activity includes inhibiting and killing action against bacteria, fungi and similar organisms.
Particularly useful compositions of. the. present. invention are those comprising soaps and detergents, and especially toilet soaps or cosmetic detergents in which the compounds of the present invention may be employed in concentrations of 0.1% to 0.5% by'weight, or even as much as 1% or more. The term detergent employed herein will be used toinclude all synthetic and natural cleansing compositions, including cationic detergents, such as dimethyl stearamido-propyl-2hydroxy-ammonium dihydrogen phosphate, anionic detergents such as commercial soaps, e.g., alkali metal soaps of hydrolyzed natural or synthetic glycerides of fatty and similar organic acids, e.g., sodium and potassium stearates or oleates, ampholytic detergents, such as sarcosine, non-ionic detergents such as polyoxypropylene polyoxyethylene condensates, natural detergents, such as starches, vegetable gums, and the like, and mixtures thereof. The term soap employed herein is used in its popular or ordinary meaning, i.e., a cleansing composition prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.
One valuable use of the compounds of the present invention is the use thereof to sanitize fibrous material such as cotton gauze, dressings, textiles, paper pulp, and the like. They also serve as antiseptic agents when incorporated in plastic or rubber compositions, prior to molding into articles of commerce, such as baby rattles, gloves, food wrappers and the like.
T able] Compound Zone of No. Formula Inhibition,
0 H S II I 1 Cl 2.0
s H 5 I1 I 2 N I 2.0
Cl 0 H S I] l 3 GN- I 3.0 Cl
01 l o H l I s H 4 Br O-N- 3.0
5 H S ll 1 5 o1 C-N I 3.0
s H S I] I 6 Br -C-N Br 3.0
1 Br Br 3 Table I--Continued A study of Table I will reveal that the germicidal potency of the compounds of the present invention do not appear to be increased substantially by the addition of extra halogen atoms to the nuclei. This is apparent when Compound No. 3 is compared with No. 4. It therefore appears that thehigh germicidal power of the compounds of the present invention is inherent irrthe 2 structural arrangement of the molecules, rather thanto the halogen substituents.
Iclaim:
1. A method of obtaining germicidal activity against Staphylococcus aureus and other bacteria, fungi ,and similar micro-organisms, comprising, i
contacting said micro-organisms with a germicidally effective concentration of at least one compound having the general formula:
t e- C? where 35 X is chlorine, bromine or iodine, A is oxygen or sulfur, a is a numeral from to 2, and b is a numeral from 1 to 3. 2. A method according to claim 1 in which the compound has the formula:
I 4. A method according to claim 1 in which the compound has the formula: 1
13r 5. A method according to claim 1 in which the compound has the formula:
sI H
Br- Br 6. A method according to claim 1 in which the compound has the formula:
go h-@411 w Xb where X is chlorine, bromine or iodine, A is oxygen or sulfur,
a is a numeral from 0 to 2, and
b is a numeral from 1 to 3.
References Cited by the Examiner Chem. Abstracts 46, 8772d 1952).
Chem. Abstracts 55, 17985d (1961).
"Chem. Abstracts 57, page 1066s, July-December 1962.
Chem. Abstracts 58, page 955s, January-June 1963.
Chem. pages 5398s-5399s.
Chem. Abstracts 6th Collective Index, 19574961,
page 5043s.
Hopper, I.V., et al.: The Preparation of Certain Thiolcarboxylic Acids and Their'Arylmides, J. Soc. Dyers Colourists 57,"pp. 69'(1941); abstracted in Chem. Ab-
stracts 35, 2484(8)-2485(2) (1941).
LEWIS GOTTS, PrimaryExaminer.
S, K. ROSE, Assistant Examiner,
Abstracts Sth Collective Index, 1947-1956,;
Claims (1)
1. A METHOD OF OBTAINING GERMICIDAL ACTIVITY AGAINST STAPHYLOCOCCUS AUREUS AND OTHER BACTERIA, FUNGI AND SIMILAR MICRO-ORGANISMS, COMPRISING, CONTACTING SAID MICRO-ORGANISMS WITH A GERMICIDALLY EFFECTIVE CONCENTRATION OF AT LEAST ONE COMPOUND HAVING THE GENERAL FORMULA:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US347007A US3243342A (en) | 1964-02-24 | 1964-02-24 | Germicidal compositions containing halogenated anilides of thiophene carboxylic acids |
| CH1692765A CH430928A (en) | 1964-02-24 | 1965-02-16 | Detergent composition with germicidal activity |
| CH207265A CH443214A (en) | 1964-02-24 | 1965-02-16 | Use of germicidal compounds consisting of halogenated anilides of thiophenecarboxylide acids for the treatment of textile materials |
| US491901A US3303201A (en) | 1964-02-24 | 1965-09-30 | Halogenated anilides of thiophene carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US347007A US3243342A (en) | 1964-02-24 | 1964-02-24 | Germicidal compositions containing halogenated anilides of thiophene carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3243342A true US3243342A (en) | 1966-03-29 |
Family
ID=23361954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US347007A Expired - Lifetime US3243342A (en) | 1964-02-24 | 1964-02-24 | Germicidal compositions containing halogenated anilides of thiophene carboxylic acids |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3243342A (en) |
| CH (2) | CH443214A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5369124A (en) * | 1992-10-02 | 1994-11-29 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides |
| WO1995027397A1 (en) * | 1994-04-11 | 1995-10-19 | Bayer Aktiengesellschaft | Microbicidal agents based on dibromo-thiophene-carboxylic acid derivatives |
-
1964
- 1964-02-24 US US347007A patent/US3243342A/en not_active Expired - Lifetime
-
1965
- 1965-02-16 CH CH207265A patent/CH443214A/en unknown
- 1965-02-16 CH CH1692765A patent/CH430928A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5369124A (en) * | 1992-10-02 | 1994-11-29 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides |
| WO1995027397A1 (en) * | 1994-04-11 | 1995-10-19 | Bayer Aktiengesellschaft | Microbicidal agents based on dibromo-thiophene-carboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH443214A (en) | 1968-01-31 |
| CH430928A (en) | 1967-02-28 |
| CH207265A4 (en) | 1967-05-31 |
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