DE1088960B - Process for the preparation of amine addition salts of 2-mercapto-pyridine-1-oxides - Google Patents
Process for the preparation of amine addition salts of 2-mercapto-pyridine-1-oxidesInfo
- Publication number
- DE1088960B DE1088960B DEO6087A DEO0006087A DE1088960B DE 1088960 B DE1088960 B DE 1088960B DE O6087 A DEO6087 A DE O6087A DE O0006087 A DEO0006087 A DE O0006087A DE 1088960 B DE1088960 B DE 1088960B
- Authority
- DE
- Germany
- Prior art keywords
- mercapto
- pyridine
- oxide
- addition salts
- preparation
- 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
- 150000001412 amines Chemical class 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 title description 4
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IOKYPACLTOWHCM-UHFFFAOYSA-N n,n-diethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(CC)CC IOKYPACLTOWHCM-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- ISLXPVNFBRXETD-UHFFFAOYSA-N CC1=CC=C(S)[N+]([O-])=C1 Chemical compound CC1=CC=C(S)[N+]([O-])=C1 ISLXPVNFBRXETD-UHFFFAOYSA-N 0.000 description 1
- OHNOZSBBYIOINT-UHFFFAOYSA-N CC1=CC=CC(S)=[N+]1[O-] Chemical compound CC1=CC=CC(S)=[N+]1[O-] OHNOZSBBYIOINT-UHFFFAOYSA-N 0.000 description 1
- UPFSVUSSQOZMHM-UHFFFAOYSA-N CC1=CC=[N+]([O-])C(S)=C1 Chemical compound CC1=CC=[N+]([O-])C(S)=C1 UPFSVUSSQOZMHM-UHFFFAOYSA-N 0.000 description 1
- IFKMNGINBCKKSK-UHFFFAOYSA-N CCC1=CC=C[N+]([O-])=C1S Chemical compound CCC1=CC=C[N+]([O-])=C1S IFKMNGINBCKKSK-UHFFFAOYSA-N 0.000 description 1
- DXUIGRJXOSACDR-UHFFFAOYSA-N CCCC1=CC=CC(S)=[N+]1[O-] Chemical compound CCCC1=CC=CC(S)=[N+]1[O-] DXUIGRJXOSACDR-UHFFFAOYSA-N 0.000 description 1
- BIRQBZZSSJRQQU-UHFFFAOYSA-N CCOC1=CC=C[N+]([O-])=C1S Chemical compound CCOC1=CC=C[N+]([O-])=C1S BIRQBZZSSJRQQU-UHFFFAOYSA-N 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001460074 Microsporum distortum Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000003141 Plant Poisoning Diseases 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- CSDXILVMMCLAJB-UHFFFAOYSA-N [O-][N+]1=CC(Br)=CC=C1S Chemical compound [O-][N+]1=CC(Br)=CC=C1S CSDXILVMMCLAJB-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Aminadditionss alzen von 2-Mercapto-pyridin-1-oxyden Die Erfindung betrifft die Herstellung von bestimmten Aminadditionssalzen von Säuren der allgemeinen Formel welche fungicide Stoffe darstellen; R bedeutet entweder ein Wasserstoff- oder Halogenatom oder einen niederen Alkyl- oder Alkoxyrest.Process for the preparation of amine addition salts of 2-mercapto-pyridine-1-oxides The invention relates to the preparation of certain amine addition salts of acids of the general formula which represent fungicides; R denotes either a hydrogen or halogen atom or a lower alkyl or alkoxy radical.
Das erfindungsgemäße Verfahren wird so durchgeführt, daß man ein
2-Mercapto-pyridin-1-oxyd der vorstehend genannten Konstitution mit einem Amin der
allgemeinen Formel
Gegenüber den ebenfalls fungiciden Ausgangsstoffen besitzen die erfindungsgemäß erhaltenen Aminadditionssalze beachtliche Vorteile. Compared to the likewise fungicidal starting materials, those according to the invention have obtained amine addition salts have considerable advantages.
Während die Ausgangsverbindungen nur schlecht in organischen Lösungsmitteln, z. B. Benzol und Leuchtpetroleum, dispergiert werden können, sind die Aminadditionssalze in diesen Lösungsmitteln löslich. Solche organischen Lösungen lassen sich jedoch viel besser auf den Pflanzen versprühen als wäßrige Lösungen, und die Folge davon ist, daß dieselben Mengen des Fungicids für eine größere bepflanzte Fläche ausreichen und somit die Spritzkosten wesentlich erniedrigt werden. Ferner werden lokale hohe Konzentrationen auf den Pflanzen und somit Pflanzenvergiftungen vermieden. While the starting compounds are poor in organic solvents, z. B. benzene and kerosene, which can be dispersed, are the amine addition salts soluble in these solvents. Such organic solutions can, however spray much better on the plants than aqueous solutions, and the consequence of it is that the same amounts of the fungicide are sufficient for a larger planted area and thus the injection costs are significantly reduced. Furthermore, local high Avoid concentrations on the plants and thus plant poisoning.
Die Aminadditionssalze besitzen sowohl die baktericide Wirkung des Aminbestandteils als auch die fungicide Wirkung des Mercaptopyridins, d. h., sie sind sowohl gegen Bakterien als auch gegen Pilze anzuwenden. The amine addition salts have both the bactericidal effect of the Amine component as well as the fungicidal effect of mercaptopyridine, d. h., they are to be used against both bacteria and fungi.
Die erfindungsgemäß erhaltenen Verbindungen sind ferner viel stabiler als die Ausgangsstoffe. So hatte bei einem Vergleichstest das 2-Mercapto-pyridin-l-oxyd nach 22 Stunden bei Raumtemperatur in einem organischen Lösungsmittel jede fungicide Wirksamkeit verloren, während die mit Cetylamin gebildete Additionsverbindung unter denselben Bedingungen ihre Wirksamkeit nahezu vollständig beibehielt. The compounds obtained according to the invention are also much more stable than the starting materials. In a comparative test, for example, it had 2-mercapto-pyridine-1-oxide after 22 hours at room temperature in an organic solvent any fungicide Effectiveness lost while the addition compound formed with cetylamine under almost completely retained its effectiveness under the same conditions.
Die erfindungsgemäß erhaltenen Verbindungen sind gegen eine große Gruppe von Mikroorganismen wirksam. The compounds obtained according to the invention are against a large one Group of microorganisms effective.
Da die erfindungsgemäß erhaltenen Verbindungen ausgedehnte baktericide und fungicide Eigenschaften besitzen, können sie als Schutzmittel für eine Vielzahl von Produkten, als Mittel zur Verhütung von Stockflecken und als Sterilisations- und Desinfektionsmittel Verwendung finden. So sind sie z. B. als fungicide Pflanzenschutzmittel, beispielsweise gegen Peronospera, die auf Reben wächst, geeignet. Since the compounds obtained according to the invention have extensive bactericidal properties and possess fungicidal properties, they can be used as preservatives for a variety of products, as a means of preventing mold stains and as a sterilization and disinfectants are used. So they are z. B. as fungicidal pesticides, for example against Peronospera, which grows on vines, suitable.
Außerdem sind sie wertvolle chemotherapeutische Mittel, insbesondere Fungicide, und können zur Behandlung von Dermatophytosis pedis und zur Eindämmung oberflächlicher Pilzinfektionen der Haut und zugänglicher Schleimhäute Anwendung finden. They are also valuable chemotherapeutic agents, in particular Fungicide, and can be used to treat and contain dermatophytosis pedis superficial fungal infections of the skin and accessible mucous membranes Find.
Als 2-Mercapto-pyridin-l-oxyde kommen z. B. in Frage: 2-Mercapto-pyridin-i -oxyd, 3-Äthoxy-2-mercapto-pyridinl-oxyd, 2-Mercapto-3-methoxy-pyndin-l -oxyd, 5-Brom-2-mercapto-pyridin-1 -oxyd, 2-Mercapto-3-äthyl-pyridinl-oxyd, 2-Mercapto-4-methyl-pyridin-1 -oxyd, 2-Mercapto-5-methyl-pyridin-1 -oxyd, 2-Mercapto-6-methyl-pyridinl-oxyd und 2-Mercapto-6-propyl-pyridin- 1-oxyd (siehe z. B. Journ. Am. Chem. Soc., Bd. 72, S. 4362 ff. £1950j, betreffend die Herstellung von substituierten 2-Mercaptopyridin-l -oxyden). As 2-mercapto-pyridine-1-oxides come z. B. in question: 2-mercapto-pyridine-i oxide, 3-ethoxy-2-mercapto-pyridine-oxide, 2-mercapto-3-methoxy-pyndine-1-oxide, 5-bromo-2-mercapto-pyridine-1 oxide, 2-mercapto-3-ethyl-pyridine-oxide, 2-mercapto-4-methyl-pyridine-1-oxide, 2-mercapto-5-methyl-pyridine-1 oxide, 2-mercapto-6-methyl-pyridine-oxide and 2-mercapto-6-propyl-pyridine-1-oxide (please refer z. B. Journ. At the. Chem. Soc., Vol. 72, pp. 4362 ff. £ 1950j, concerning the production of substituted 2-mercaptopyridine-1-oxides).
Die folgenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.
Beispiel 1 Eine Lösung von 1,27 g 2-Mercapto-pyndin-l-oxyd in 3 cm3 absolutem Alkohol wird zu einer Lösung von 2,41 g Cetylamin in 1 cm3 absolutem Alkohol zugegeben. Dann fügt man etwa 25 cm3 trockenen Äther hinzu, und nach Abkühlung und Kratzen der Gefäßwände erfolgt Kristallisation. Der etwa 2,7 g wiegende kristalline Feststoff, der bei etwa 78 bis 80"C schmilzt, ist das Cetylaminsalz von 2-Mercapto-pyridin-1 -oxyd (nach Umkristallisation aus Alkohol-Äther-Gemisch schmilzt die Verbindung bei etwa 79 bis 81"C). Example 1 A solution of 1.27 g of 2-mercapto-pyndine-1-oxide in 3 cm3 absolute alcohol becomes a solution of 2.41 g of cetylamine in 1 cm3 of absolute alcohol admitted. Then add about 25 cm3 of dry ether, and after cooling down and Crystallization occurs when the vessel walls are scratched. The crystalline weighs about 2.7 g Solid, which melts at about 78 to 80 "C, is the cetylamine salt of 2-mercapto-pyridine-1 oxide (after recrystallization from an alcohol-ether mixture, the compound melts at about 79 to 81 "C).
Bei Verwendung der äquivalenten Menge Octylamin an Stelle von Cetylamin im Beispiel 1 erhält man das Octylaminsalz von 2-Mercapto-pyridin-1 -oxyd. When using the equivalent amount of octylamine instead of cetylamine in Example 1, the octylamine salt of 2-mercapto-pyridine-1-oxide is obtained.
Beispiel 2 Eine Lösung von 1,27 g 2-Mercapto-pyridin-l-oxyd in 5 cm3 absolutem Alkohol wird zu 2,69 g Cetyl-dimethylamin zugegeben. Man fügt dann etwa 25 cm3 trockenen Äther hinzu, und nach Abkühlung und Kratzen der Gefäßwände erfolgt Kristallisation. Der etwa 2g wiegende und bei 62 bis 630 C schmelzende Feststoff ist das Cetyldimethyl-aminsalz von 2-Mercapto-pyridin-1 -oxyd. Nach Umkristallisation aus Alkohol-Äther-Gemisch beträgt der Schmelzpunkt 63 bis 64"C. Bei Verwendung der äquivalenten Menge von Lauryl-diäthyl-amin an Stelle von Cetyl-dimethyl-amin im Beispiel 2 erhält man das Lauryldiäthyl-aminsalz von 2-Mercapto-pyndin-l-oxyd. Example 2 A solution of 1.27 g of 2-mercapto-pyridine-1-oxide in 5 cm3 of absolute alcohol is added to 2.69 g of cetyldimethylamine. One then adds Add about 25 cm3 of dry ether, and after cooling and scraping the vessel walls crystallization occurs. The solid, which weighs about 2g and melts at 62 to 630 ° C is the cetyldimethylamine salt of 2-mercapto-pyridine-1-oxide. After recrystallization from an alcohol-ether mixture the melting point is 63 to 64 "C. When using the equivalent amount of lauryl diethyl amine instead of cetyl dimethyl amine im Example 2 gives the lauryl diethyl amine salt of 2-mercapto-pyndine-1-oxide.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1088960XA | 1953-05-19 | 1953-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1088960B true DE1088960B (en) | 1960-09-15 |
Family
ID=22324679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEO6087A Pending DE1088960B (en) | 1953-05-19 | 1954-05-19 | Process for the preparation of amine addition salts of 2-mercapto-pyridine-1-oxides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1088960B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833013A1 (en) * | 1977-07-28 | 1979-02-15 | Oreal | NEW ALUMINUM-SULFUR COMPOUND, METHOD OF MANUFACTURING IT, AND MEANS OF CONTAINING THIS COMPOUND |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB679382A (en) * | 1949-02-11 | 1952-09-17 | Monsanto Chemicals | Improvements in or relating to quaternary ammonium compounds |
-
1954
- 1954-05-19 DE DEO6087A patent/DE1088960B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB679382A (en) * | 1949-02-11 | 1952-09-17 | Monsanto Chemicals | Improvements in or relating to quaternary ammonium compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833013A1 (en) * | 1977-07-28 | 1979-02-15 | Oreal | NEW ALUMINUM-SULFUR COMPOUND, METHOD OF MANUFACTURING IT, AND MEANS OF CONTAINING THIS COMPOUND |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1695274A1 (en) | Process for the preparation of new imidazole carboxylates | |
| CH380734A (en) | Process for the preparation of new s-triazine derivatives | |
| CH641010A5 (en) | PARASITENBEKAEMPFUNGSMITTEL FOR controlling harmful microorganisms. | |
| DE1174018B (en) | Preparations for combating harmful microorganisms | |
| DE2641836B1 (en) | Alkylated polyamines, their production and use as microbicides | |
| AT334134B (en) | FIGHTING FUNGI PEST | |
| DE2635389C2 (en) | Preservatives and disinfectants | |
| DE1088960B (en) | Process for the preparation of amine addition salts of 2-mercapto-pyridine-1-oxides | |
| CH635227A5 (en) | Parasitenbekaempfungsmittel. | |
| DE2244778C3 (en) | 1 -n-dodecylaminomethyl-2-aminocyclopentane, its production and use as a microbicidal active ingredient | |
| DE1034645B (en) | Process for the production of neutral sulfuric acid esters | |
| DE1668616B2 (en) | BISDITHIOCARBAMTE, PROCESS FOR THEIR PRODUCTION AND FUNGICIDAL AGENT CONTAINING THIS | |
| EP0043125B1 (en) | Aluminium-organic compounds, preparation of these compounds, cosmetic compositions containing these compounds as active agents and use of these compositions to combat and prevent seborrhoea | |
| DE2144125A1 (en) | Dithiocarboamic acid salts or urea derivs - from urea derivs and dithio-carbamic acid salts, fungicides, microbicides | |
| DE2744353A1 (en) | HYDANTOIN DERIVATIVES, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE | |
| DE2508420A1 (en) | QUATERNAERE IMIDAZOLIUM JOINTS | |
| AT268271B (en) | Process for the preparation of new imidazole carboxylates and their salts | |
| DE953125C (en) | Agent for combating microorganisms such as fungi, bacteria and protozoa | |
| DE2247370C3 (en) | 1,3,3-Trimethyl-1-noctylaminomethyl-5-n-octylamino-cyclohexane, process for their preparation and their use as a microbicidal active ingredient | |
| DE1593592C (en) | Process for the preparation of adducts of organic mercury compounds which are soluble or dispersible in water or water-miscible solvents and their use as fungicides and bactericides | |
| DE1966863C3 (en) | N, N'-bis [(I -formamido-2 ^, 2.trichlor) ethyl] ethylenediamines, and pesticides which contain these compounds as active ingredients | |
| DE1169948B (en) | Process for the production of antibacterially active N, N'-alkylene-1, 1'-alkylene-bis- (4-aminochinolinium halides) | |
| AT353984B (en) | MICROBICIDAL PREPARATION | |
| DE1140578B (en) | Process for the preparation of quaternary ammonium salts of 2-mercaptopyridine-1-oxides | |
| DE2144123A1 (en) | Dithiocarbamic acid heavy metal salts and guanidines - complexes - fungicides and microbicides |