CS215487B1 - N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation - Google Patents

N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation Download PDF

Info

Publication number
CS215487B1
CS215487B1 CS105781A CS105781A CS215487B1 CS 215487 B1 CS215487 B1 CS 215487B1 CS 105781 A CS105781 A CS 105781A CS 105781 A CS105781 A CS 105781A CS 215487 B1 CS215487 B1 CS 215487B1
Authority
CS
Czechoslovakia
Prior art keywords
bis
ethanediamine
alkylmethyl
hydrogen peroxide
mic
Prior art date
Application number
CS105781A
Other languages
Czech (cs)
Slovak (sk)
Inventor
Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Original Assignee
Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ferdinand Devinsky, Ivan Lacko, Ludovit Krasnec filed Critical Ferdinand Devinsky
Priority to CS105781A priority Critical patent/CS215487B1/en
Publication of CS215487B1 publication Critical patent/CS215487B1/en

Links

Landscapes

  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Vynález sa týká N,N'-bis(alkylmetyl)-l,2-etándiamíndioxidov všeobecného vzorca 9 9 R - N - CH2 - CH2 - N - R OH CH 5 3 kde R značí 8 až 14 atomov uhlíka v alkylovom reťazci a sposobu přípravy týchto zlúčenín z N,N'- bis(alkylmetyl)-l,2-etándiamínov oxidáciou vodným roztokom peroxidu vodíka. Finálně zlúčeniny majú výrazný antimikrobiálny účinok ako i povrchovoaktívne vlastnosti.The invention relates to N,N'-bis(alkylmethyl)-1,2-ethanediamine dioxides of the general formula 9 9 R - N - CH2 - CH2 - N - R OH CH 5 3 where R denotes 8 to 14 carbon atoms in the alkyl chain and to a method of preparing these compounds from N,N'-bis(alkylmethyl)-1,2-ethanediamines by oxidation with an aqueous solution of hydrogen peroxide. Finally, the compounds have a significant antimicrobial effect as well as surface-active properties.

Description

Vynález sa týká N,N'-bis(alkylmetyl)-l,2-etándiamíndioxidov všeobecného vzorcaThe invention relates to N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides of the general formula

R - N - CH- - CH- - N - R ( 2 R ,R - N - CH - CH - N - R ( 2 R,

CH5 ch5 kde R značí alkylový reťazec s počtom atómov uhlíka 8 až 14.CH 5 CH 5 wherein R is an alkyl chain having a carbon number 8 to 14.

Z hlediska antimikrobiálnej účinnosti patria nearomatické amínoxidy, ktoré vo svojej molekule obsahujú najmenej jeden dlhý alkylový reťazec medzi účinné zlúčeniny. Okrem biologického účinku vykazuj ú tieto látky aj povrchovoaktívne vlastnosti.In terms of antimicrobial activity, non-aromatic amine oxides which contain at least one long alkyl chain in their molecule are among the active compounds. In addition to their biological activity, they also have surface-active properties.

Doteraz sú známe amínoxidy odvodené od 1,2-etándiamínu typu Ν,Ν'-bisdialkyl, kde alkylový reťazec obsahuje 1 alebo 2 atomy uhlíka. Tieto zlúčeniny sú však antimikrobiálne ako i z hladiska povrchovej aktivity neúčinné.Hitherto known amine oxides are derived from 1,2-ethanediamine of the Ν, Ν'-bisdialkyl type wherein the alkyl chain contains 1 or 2 carbon atoms. However, these compounds are ineffective as well as antimicrobial and surface active.

Zlúčeniny, ktoré sú predmetom vynálezu, sú látky nové, doteraz v chemickej literatúre neopísané, u ktorých sa zistili doteraz neznáme účinky na mikroorganizmy.The compounds of the invention are novel substances which have not been previously described in the chemical literature and have been found to have unknown effects on microorganisms.

V príkladoch sú uvedené vybrané zlúčeniny, ktoré sú predmetom vynálezu a metoda ich přípravy ako i ich charakterizácia spolu s uvedením ich antimikrobiálnej účinnosti (udanej ako minimálnaThe examples show selected compounds of the invention and methods for their preparation as well as their characterization together with an indication of their antimicrobial activity (given as the minimum

Claims (2)

PREDMET 1. N,N'-bis(alkylmetyl)-1,2-etándiamíndioxidy všeobecného vzorca 0 0 B - N - CHg - 0¾ - N - R ch3 Íh3 kde R značí alkylový reťazec obsahujúci 8 až 14 atómov uhlíka.PREDMET 1. N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides of the formula 0 0 B - N - CH 3 --O 3 --N - R 3 CH 3 where R represents an alkyl chain containing from 8 to 14 carbon atoms. 2. Spósob přípravy zlúčenín všeobecného vzor- 215487 inhibičná koncentrácia — MIC - v pg/ml na kmeňóch Staphylococcus aureus, Escherichia coli a Candida albicans). Příklad 1 0,1 mol N,N'-bis(metylnonyl)- 1,2-etándiamínu sa rozpustí v metanole a pri teplote 40 až 50 °C sa přidá 0,3 mol 20 až 30 % vodného roztoku peroxidu vodíka. Zmes sa nechá reagovat’ 4 hodiny pri teplote 60 až 70 °C. Po ochladení sa nadbytocný peroxid vodíka rozloží, rozpúšťadlo a voda sa odpaří a suchý zvyšok sa prekryštalizuje zo suchého acetonu. Vzniká N,N'-bis(metylnonyl)-l,2etándiamíndioxid s t. t. 128. až 130 °C; Rt = 0,85 (Silufol; sústava aceton : 1 N HC1 (1 : 1), detekcia Dragendorfovým činidlom); výťažok 84 % teorie; MIC 50; 200; 90; IČ-spektrálna charakteristika: vNO : 939 a 947 cm'1 (nujol). Příklad 2 Pracovný postup ako i navážky sú zhodné s postupom uvedeným v příklade 1, do reakcie sa použil N,N'-bis(metyltridecyl)-1,2-etándiamín. Produkt N,N'-bis(metyltridecyl)-l,2-etándiamíndioxid má t. t. 107 až 110 °C; R( = 0,45; výťažok 84 % teorie; MIC 70; 800; 70; IČ-spektrálna charakteristika: vNO : 918 a 936 cm-1 (nujol). Všetký zlúčeniny, ktoré sú predmetom vynálezu sa identifikovali elementárnou analýzou a spektrálnými metodami. VYNÁLEZU ca ako v bode 1, vyznačený tým, že sa nechá oxidovat’ N,N'-bis(alkylmetyl)-l,2-etándiamín všeobecného vzorca R - N - CH- - OH- - N - R I I CH, CH, 7 P kde R má ten istý význam ako v bode 1,20 až 30 % vodným roztokom peroxidu vodíka pri teplotách 40 až 70 °C.2. A method of preparing compounds of formula 215487 inhibitory concentration - MIC - in pg / ml on Staphylococcus aureus, Escherichia coli and Candida albicans strains. EXAMPLE 1 0.1 mol of N, N'-bis (methylnonyl) -1,2-ethanediamine was dissolved in methanol and 0.3 mol of a 20-30% aqueous hydrogen peroxide solution was added at 40-50 ° C. The mixture is reacted for 4 hours at 60-70 ° C. After cooling, the excess hydrogen peroxide is decomposed, the solvent and water are evaporated and the dry residue is recrystallized from dry acetone. N, N'-bis (methylnonyl) -1,2-ethanediamine dioxide is obtained, m.p. 128-130 ° C; R t = 0.85 (Silufol; acetone: 1 N HCl (1: 1), Dragendorf reagent detection); yield 84% of theory; MIC 50; 200; 90; IR spectral characteristic: vNO: 939 and 947 cm -1 (nujol). EXAMPLE 2 The working procedure as well as the batches are as described in Example 1, using N, N'-bis (methyltridecyl) -1,2-ethanediamine. The product N, N'-bis (methyltridecyl) -1,2-ethanediamine dioxide has a melting point of 107-110 ° C; R (= 0.45; yield 84% of theory; MIC 70; 800; 70; IR spectral characteristic: vNO: 918 and 936 cm -1 (nujol). All compounds of the invention were identified by elemental analysis and spectral methods DISCLOSURE OF THE INVENTION as in 1, characterized in that N, N'-bis (alkylmethyl) -1,2-ethanediamine of the general formula R - N - CH - OH - N - RII CH, CH is allowed to be oxidized, Wherein P is the same as in 1.20 to 30% aqueous hydrogen peroxide at 40-70 ° C.
CS105781A 1981-02-16 1981-02-16 N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation CS215487B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS105781A CS215487B1 (en) 1981-02-16 1981-02-16 N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS105781A CS215487B1 (en) 1981-02-16 1981-02-16 N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation

Publications (1)

Publication Number Publication Date
CS215487B1 true CS215487B1 (en) 1982-08-27

Family

ID=5343962

Family Applications (1)

Application Number Title Priority Date Filing Date
CS105781A CS215487B1 (en) 1981-02-16 1981-02-16 N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation

Country Status (1)

Country Link
CS (1) CS215487B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109721511A (en) * 2019-01-21 2019-05-07 北京工商大学 A kind of preparation method of the Shuangzi amine oxide of the ethyl of ester group containing alkyl
JP2021109839A (en) * 2020-01-08 2021-08-02 株式会社ニイタカ Gemini compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109721511A (en) * 2019-01-21 2019-05-07 北京工商大学 A kind of preparation method of the Shuangzi amine oxide of the ethyl of ester group containing alkyl
JP2021109839A (en) * 2020-01-08 2021-08-02 株式会社ニイタカ Gemini compound
JP7432185B2 (en) 2020-01-08 2024-02-16 株式会社ニイタカ gemini type compound

Similar Documents

Publication Publication Date Title
US3320229A (en) Complexes of guanidines with completely halogenated acetones
DE3786365T2 (en) 5H-1,3,4-thiadiazolo [3,2-a] pyrimidin-5-one derivatives and horticultural and agricultural fungicidal compositions containing them.
GB975046A (en) Halo-pyridyl phosphorus compounds
IE46471B1 (en) Novel oxime derivatives and their preparation
DE2513732A1 (en) MICROBICIDALS AND GROWTH REGULATORY AGENTS
DE2513730A1 (en) HALOGEN ACETANILIDE AS MICROBICIDAL ACTIVE INGREDIENTS
FI923033A0 (en) N-PHENYLTIOUREADERIVAT OCH PHARMACEUTICAL ANVAENDNING AV DEM.
DE2513789A1 (en) HALOACYLANILIDES AS MICROBICIDAL ACTIVE INGREDIENTS
DE2741437A1 (en) ANILINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND PEST CONTROL
US3178336A (en) Bis-dithiocarbamate fungicides
KR880001998B1 (en) Process for the preparing tetrazoles
CS215487B1 (en) N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides and their preparation
US3177224A (en) N-trichloromethylthiohydantoins
US3594362A (en) Urea complexes
US3624253A (en) Hexamethylenetetramine adducts with haloacetic acid esters
US3027371A (en) Molybdenum-containing derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same
US3660465A (en) Ethynylene containing n-phenyl carbamates
EP0063464A1 (en) Fungicidal composition comprising alpha-substituted ethylphosphinic acids or their salts, and method of preventing or curing plant disease using them
RO87039B1 (en) Process for the preparation of penicillanic acid derivatives
US3879455A (en) Herbicide compositions
US3711271A (en) Method for controlling algae
US3423416A (en) Novel aromatic n-heterocyclic esters of diarylcarbamoyl or diarylthiocarbamoyl halides
US4262127A (en) 3-Alkoxy-2-alkylisothiazolium salts and their derivatives
US2591589A (en) Gamma-nitroalkyl-alpha,beta-dichloro-gamma-crotonolactones
US3660580A (en) Use of certain oxime esters in controlling fungi upon cellulosic materials