DE1278671B - Antiseptic detergent - Google Patents
Antiseptic detergentInfo
- Publication number
- DE1278671B DE1278671B DEST25666A DEST025666A DE1278671B DE 1278671 B DE1278671 B DE 1278671B DE ST25666 A DEST25666 A DE ST25666A DE ST025666 A DEST025666 A DE ST025666A DE 1278671 B DE1278671 B DE 1278671B
- Authority
- DE
- Germany
- Prior art keywords
- atom
- cleaning agent
- dione
- oxygen
- active ingredient
- 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.)
- Pending
Links
- 230000002421 anti-septic effect Effects 0.000 title claims description 5
- 239000003599 detergent Substances 0.000 title description 5
- 239000002994 raw material Substances 0.000 claims description 10
- 239000012459 cleaning agent Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000000344 soap Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- -1 amphoteric Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- UXTZUUVTGMDXNG-UHFFFAOYSA-N 1,2-benzoxazine-3,4-dione Chemical class C1=CC=C2C(=O)C(=O)NOC2=C1 UXTZUUVTGMDXNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000271 synthetic detergent Substances 0.000 claims 1
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GHNLJDPNIAIWOQ-UHFFFAOYSA-N 2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NC=CC2=C1 GHNLJDPNIAIWOQ-UHFFFAOYSA-N 0.000 description 1
- AIPDYRUQGNTLLE-UHFFFAOYSA-N 3-phenyl-1,3-benzoxazine-2,4-dione Chemical class O=C1OC=2C=CC=CC=2C(=O)N1C1=CC=CC=C1 AIPDYRUQGNTLLE-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 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 1
- 244000199866 Lactobacillus casei Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- WPDGFKWDLXLZQM-UHFFFAOYSA-N chloroethane formic acid Chemical compound C(=O)O.C(C)Cl WPDGFKWDLXLZQM-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical class [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/08—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paper (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. Cl.:Int. Cl .:
Deutsche Kl.:German class:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
ClIdClId
A611
C07dA611
C07d
23e-2
30i-3
12 p -3 23e-2
30i-3
12 p -3
P 12 78 671.9-41 (St 25666)P 12 78 671.9-41 (St 25666)
20. Juli 1966July 20, 1966
26. September 196826th September 1968
Die Erfindung betrifft ein antiseptisches Reinigungsmittel mit einem Gehalt an antimikrobiell wirksamen Benzoazindionderivaten einschließlich Benzothiazindion- und Benzoxazindionverbindungen.The invention relates to an antiseptic cleaning agent with an antimicrobial content Benzoazinedione derivatives including benzothiazinedione and benzoxazinedione compounds.
Die Benzoazindionderivate entsprechen der allgemeinen FormelThe benzoazinedione derivatives correspond to the general formula
Antiseptisches ReinigungsmittelAntiseptic detergent
R1R2R3 R 1 R 2 R 3
in der Y ein Sauerstoff- oder Schwefelatom, Z ein Kohlenstoff- oder Schwefelatom und R1 bis R6 unabhängig voneinander Wasserstoff-, Chlor-, Bromoder Jodatome, ein oder zwei von ihnen auch Tnfluormethylreste darstellen, mindestens eines von R1 bis R6 jedoch kein Wasserstoffatom ist, wenn Y ein Sauerstoffatom und Z ein Kohlenstoffatom darstellt.in which Y an oxygen or sulfur atom, Z a carbon or sulfur atom and R 1 to R 6 independently of one another hydrogen, chlorine, bromine or iodine atoms, one or two of them also represent fluoromethyl radicals, but at least one of R 1 to R 6 is not a hydrogen atom when Y is an oxygen atom and Z is a carbon atom.
In der Arbeit von Stanseth, Baker und Roman (J. Med. Chem., Bd. 6, 1963, S. 212ff.) ist beschrieben, daß substituierte 3-Phenyl-l,3-benzoxazjn-2,4-dione eine hohe bactericide Wirkung besitzen.In the work of Stanseth, Baker, and Roman (J. Med. Chem., Vol. 6, 1963, p. 212ff.) It is described that substituted 3-phenyl-1,3-benzoxazin-2,4-diones have a high bactericidal effect.
Die Erfindung betrifft nun ein antiseptisches Reinigungsmittel auf Basis von Seifen und/oder synthetischen Waschrohstoffen, das dadurch gekennzeichnet ist, daß es ein antimikrobiell wirksames Benzoazindionderivat der allgemeinen FormelThe invention now relates to an antiseptic cleaning agent based on soaps and / or synthetic Washing raw materials, which is characterized in that it is an antimicrobially active benzoazinedione derivative the general formula
in der Y ein Sauerstoff- oder Schwefelatom, Z ein 4c Kohlenstoff- oder Schwefelatom und R1 bis R6 unabhängig voneinander Wasserstoff-, Chlor-, Bromoder Jodatome, ein oder zwei von ihnen auch Tnfluormethylreste darstellen, und mindestens einer der Reste R1 bis R6 kein Wasserstoffatom ist, wenn Y ein Sauerstoffatom und Z ein Kohlenstoffatom darstellt, als Wirkstoff enthält. Vorteilhaft kann in dem neuen Reinigungsmittel ein anionischer, amphoterer, kationischer oder nichtipnischer Waschrohstoff vorhanden sein.in which Y is an oxygen or sulfur atom, Z is a carbon or sulfur atom and R 1 to R 6 independently of one another are hydrogen, chlorine, bromine or iodine atoms, one or two of them also represent fluoromethyl radicals, and at least one of the radicals R 1 to R 6 is not a hydrogen atom when Y is an oxygen atom and Z is a carbon atom, contains as an active ingredient. An anionic, amphoteric, cationic or non-Finnish washing raw material can advantageously be present in the new cleaning agent.
Die verwendeten Benzoazindionderivate werden durch Umsetzen von substituierten SalicylanilidenThe benzoazinedione derivatives used are made by reacting substituted salicylanilides
Anmelder:Applicant:
Stecker Chemicals, Inc.,Connector Chemicals, Inc.,
Ho-Ho-Kus, N. J. (V. St. A.)Ho-Ho-Kus, N. J. (V. St. A.)
Vertreter:Representative:
Dr. K. Th. Hegel, Patentanwalt,Dr. K. Th. Hegel, patent attorney,
2000 Hamburg 50, Große Bergstr. 2232000 Hamburg 50, Große Bergstr. 223
Als Erfinder benannt:Named as inventor:
Winthrop E. Lange, Needham, Mass.;Winthrop E. Lange, Needham, Mass .;
Jon C. Anderson, Brockton, Mass. (V. St. A.)Jon C. Anderson, Brockton, Mass. (V. St. A.)
Beanspruchte Priorität: V. St. v. Amerika vom 11. Oktober 1965
(494894)Claimed priority: V. St. v. America October 11, 1965
(494894)
mit Ameisensäure-äthylchlorid oder Thionylchlorid gewonnen. Die Wirkstoffe können in Seifen und Waschrohstoffen in Konzentrationen zwischen 10 ppm bis 5 Gewichtsprozent und darüber verwendet werden. Die Wirkstoffkonzentration kann beispielsweise 50 oder 100 ppm, 0,01%, 0,1%, 0,5% oder 1% betragen. Benzoazindionderivate können insbesondere in Toilettenseifen und kosmetischen Reinigungsmitteln Verwendung finden. Unter der Bezeichnung »Reinigungsmittel« werden dabei alle natürlichen oder synthetischen, reinigend wirkenden Produkte mit einem Gehalt an anionaktiven Waschrohstoffen, beispielsweise handelsübliche Seifen wie die Alkaliseifen hydrolysierter natürlicher oder synthetischer Glyceride von Fettsäuren oder ähnlichen Säuren, insbesondere Natrium- oder Kaliumstearaten oder -oleaten, kationischen Waschrohstoffen, wie beispielsweise Dimethylstearamid-propyl-2-hydroxy-ammoniumdihydrogenphosphat, ampholytischen Waschrohstoffen, beispielsweise Sarkosine, nichtionischen Waschrohstoffen, beispielsweise Polyoxypropylen-Polyoxyäthylen-Kondensationsprodukte, natürlichen Waschrohstoffen, wie beispielsweise Stärke oder Pflanzengummi u. dgl., oder deren Mischungen verstanden. Einer der großen Vorzüge der neuen Reinigungsmittel besteht in der Tatsache, daß die mit Benzoazindionverbindungen versetzten Seifen usw. auch unter dem Einfluß von Sonnenlicht keinerlei Verfärbung zeigen und ihr ursprüngliches Aussehen unverändertobtained with formic acid ethyl chloride or thionyl chloride. The active ingredients can be used in soaps and detergent raw materials in concentrations between 10 ppm to 5 percent by weight and above. The active ingredient concentration can be, for example, 50 or 100 ppm, 0.01%, 0.1%, 0.5% or 1%. Benzoazinedione derivatives can be used in particular in toilet soaps and cosmetic cleaning agents. The term "cleaning agent" refers to all natural or synthetic, cleaning products with a content of anionic detergent raw materials, for example commercially available soaps such as the alkali soaps of hydrolyzed natural or synthetic glycerides of fatty acids or similar acids, in particular sodium or potassium stearates or oleates, cationic Washing raw materials, such as dimethylstearamide-propyl-2-hydroxy-ammonium dihydrogen phosphate, ampholytic washing raw materials, such as sarcosines, nonionic washing raw materials, for example polyoxypropylene-polyoxyethylene condensation products, natural washing raw materials such as starch or vegetable gum and the like. Or their mixtures. One of the great advantages of the new detergents is the fact that the soaps, etc. to which benzoazinedione compounds have been added do not show any discoloration even under the influence of sunlight and their original appearance remains unchanged
«09 618/541«09 618/541
IOIO
beibehalten. Diese Beständigkeit war nicht zu erwarten. maintained. This consistency was not to be expected.
Beispiele der erfindungsgemäß verwendeten Wirkstoffe sind:Examples of the active ingredients used according to the invention are:
6,8-Dibrom-3-(3-trifluormethylphenyl)-5,6-benzol,3-oxazin-2,4-dion, Schmelzpunkt von 233 bis 235° C;6,8-dibromo-3- (3-trifluoromethylphenyl) -5,6-benzene, 3-oxazine-2,4-dione, Melting point from 233 to 235 ° C;
6-Brom-3-(4'-bromphenyl)-5,6-benzo-l,3-oxazin-2,4-dion, Schmelzpunkt 235 bis 236° C;
3 - (3'- Trifluormethylphenyl) - 5,6 - benzo -1,3 - oxazin-2,4-dion,
Schmelzpunkt 198 bis 1990C;
3 -(2'- Chlor - 3'- trifluormethylphenyl) - 5,6 - benzol,3-oxazin-2,4-dion,
Schmelzpunkt 195 bis 198° C; 6,8 - Dijod - 3 - (3',5' - bis - trifluormethylphenyl)- 1S
5,6-benzo-l,3-oxazin-2,4-dion, Schmelzpunkt 214 bis 218°C;6-bromo-3- (4'-bromophenyl) -5,6-benzo-1,3-oxazine-2,4-dione, melting point 235 to 236 ° C;
3 - (3'-trifluoromethylphenyl) -5,6-benzo -1,3-oxazine-2,4-dione, melting point 198 to 199 0 C;
3 - (2'-chloro - 3'-trifluoromethylphenyl) - 5,6 - benzene, 3-oxazine-2,4-dione, melting point 195 to 198 ° C; 6,8 - diiodo - 3 - (3 ', 5' - bis - trifluoromethylphenyl) - 1 S 5,6-benzo-l, 3-oxazin-2,4-dione, melting point 214-218 ° C;
6,8 - Dichlor - 7 - trifluormethyl - 3 - (4' - jodphenyl)-5,6-benzo-l,3-oxazin-2,4-dion, Schmelzpunkt 220 bis 224°C;6,8 - dichloro - 7 - trifluoromethyl - 3 - (4 '- iodophenyl) -5,6-benzo-1,3-oxazine-2,4-dione, Melting point 220 to 224 ° C;
3-(4'-Bromphenyl)-5,6-benzo-l,3-thiazin-2,4-dion, Schmelzpunkt 236 bis 238° C;3- (4'-bromophenyl) -5,6-benzo-1,3-thiazine-2,4-dione, Melting point 236 to 238 ° C;
6,8 - Dibrom - 3 - (l',3'- dichlor - 4'- trifluormethylphenyl)-5,6-benzo-l,3-thiazin-2,4-dion, Schmelzpunk't 238 bis 2400C;6.8 - dibromo - 3 - (l ', 3'-dichloro - 4'-trifluoromethylphenyl) -5,6-benzo-1,3-thiazine-2,4-dione, melting point 238 to 240 0 C;
6,8-Dibrom-3-(3'-trifluormethylphenyl)-5,6-benzo-l,2,3-oxathiazin-2,4-dion, Schmelzpunkt 190.6,8-dibromo-3- (3'-trifluoromethylphenyl) -5,6-benzo-l, 2,3-oxathiazine-2,4-dione, Melting point 190.
bis 195° C;up to 195 ° C;
3 - Phenyl - 5,6 - benzo -1,2,3 - dithiazin - 2,4 - dion, Schmelzpunkt 242 bis 2450C.3 - phenyl - 5,6 - benzo -1,2,3 - dithiazine - 2,4 - dione, melting point 242 to 245 0 C.
Die erfindungsgemäß verwendeten Wirkstoffe haben sich unter anderem auch gegen Mikroorganismen wie S. typhi, E. coli, L. casei als wirksam erwiesen. Das - Brom - 3 - (4'- bromphenyl) - 5,6 - benzo -1,3 - oxazin-2,4-dion ist besonders gegen Alkaligines fecalis, einem gramnegativen Organismus, wirksam.The active ingredients used according to the invention have, inter alia, also against microorganisms such as S. typhi, E. coli, L. casei shown to be effective. The - bromo - 3 - (4'-bromophenyl) - 5,6 - benzo -1,3 - oxazine-2,4-dione is particularly effective against Alkaligines fecalis, a gram-negative organism.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49489465A | 1965-10-11 | 1965-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1278671B true DE1278671B (en) | 1968-09-26 |
Family
ID=23966402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST25666A Pending DE1278671B (en) | 1965-10-11 | 1966-07-20 | Antiseptic detergent |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH475008A (en) |
| DE (1) | DE1278671B (en) |
| GB (1) | GB1099865A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2202872A (en) * | 1987-02-13 | 1988-10-05 | Grace W R & Co | Pitch control aid and dye assistant |
| US5031245B1 (en) * | 1989-04-20 | 1996-09-10 | Smith & Nephew | Gloves their manufacture and use |
| US5261421A (en) * | 1988-04-23 | 1993-11-16 | Smith & Nephew Plc | Gloves, their manufacture and use |
| KR20090090406A (en) | 2000-12-18 | 2009-08-25 | 가부시키가이샤 이야쿠 분지 셋케이 겐쿠쇼 | Inflammatory Cytokine Production Free Inhibitor |
| WO2003103656A1 (en) | 2002-06-06 | 2003-12-18 | 株式会社医薬分子設計研究所 | O-substituted hydroxyaryl derivatives |
| EA009701B1 (en) | 2002-06-06 | 2008-02-28 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Antiallergic |
-
1966
- 1966-06-01 GB GB2437566A patent/GB1099865A/en not_active Expired
- 1966-07-20 DE DEST25666A patent/DE1278671B/en active Pending
- 1966-07-27 CH CH1084566A patent/CH475008A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1099865A (en) | 1968-01-17 |
| CH475008A (en) | 1969-07-15 |
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