CS239430B1 - N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation - Google Patents
N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation Download PDFInfo
- Publication number
- CS239430B1 CS239430B1 CS843553A CS355384A CS239430B1 CS 239430 B1 CS239430 B1 CS 239430B1 CS 843553 A CS843553 A CS 843553A CS 355384 A CS355384 A CS 355384A CS 239430 B1 CS239430 B1 CS 239430B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- bis
- dimethyl
- preparation
- compounds
- dibromides
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 title description 2
- -1 p-tert-butylphenyl Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- SFDZPIDEIFZWQV-UHFFFAOYSA-N acetic acid;barium Chemical compound [Ba].CC(O)=O SFDZPIDEIFZWQV-UHFFFAOYSA-N 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000000845 anti-microbial effect Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000645 desinfectant Substances 0.000 abstract description 2
- 241000894006 Bacteria Species 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UPCOSYBELNEQAU-UHFFFAOYSA-L (2-decoxy-2-oxoethyl)-[2-[(2-decoxy-2-oxoethyl)-dimethylazaniumyl]ethyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCOC(=O)C[N+](C)(C)CC[N+](C)(C)CC(=O)OCCCCCCCCCC UPCOSYBELNEQAU-UHFFFAOYSA-L 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- SSURCGGGQUWIHH-UHFFFAOYSA-N NNON Chemical compound NNON SSURCGGGQUWIHH-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical class OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Vynález sa týká N,N -bis/(alkoxykarbonylmetyl)dlmetyl/-1,2-eténdiemónlumdibromldov všeobecného vzorca CH, CH, R-0-C-CH2-+N-CH2-CH2-N+-CH2-C-0-R 2 Br CH, CH, kde R znamená lineárny alebo rozvětvený alkylový reťasec s počtom atomov uhlíka 6 až 16 alebo p-terc.butylfenyl a apOsobu přípravy týchto zlúčenín, ktorý spočívá v reakcií príeluSného esteru kyseliny bromoctovej s N,N -bisdimetyl-1,2-etándiamlnom v prostředí metylkyanidu pri teplotách 20 až 80 °C. Pinálne zlúčeniny majú výrazné povrchovoaktlvne vlastnosti a antimikróbny účinok tak na grampozltívne a gramnegatívne baktérie ako aj na kvasinky a preto sú použitelné, najúcinnejSle z nich, na dezinfekclu, konzerváciu, ako pomocné povrchovoaktlvne látky a pod..The invention relates to N, N-bis ((alkoxycarbonylmethyl) dlmethyl) -1,2-ethanediemone dibromide. formula CH, CH, R-O-C-CH2-N-CH2-CH2-N + -CH2-C-O-R2 Br CH, CH, wherein R is linear or branched an alkyl chain having carbon numbers 6 to 16 or p-tert-butylphenyl and apo the preparation of these compounds in the reaction of an acidic ester bromoacetate with N, N-bis-dimethyl-1,2-ethanediamine in the medium of cyanide at temperatures of 20 to 80 ° C. Pineal compounds have pronounced surface-active properties properties and antimicrobial effect and gram-negative and gram-negative bacteria as well as yeast and are therefore useful, the most effective of them, on disinfectant, preservation as an auxiliary surfactant substances and the like ..
Description
239430 2
Vynález sa týká H,N'-bie/(alkoxykarbonyl)dimetyl/-1,2-etándiamóniumdibromidov vše-obecného vzorca
kde R znamená lineárny alebo rozvětvený alkylový retazec a počtom atoaov uhlíka 6 až 16alebo p-terc.butylfenyl a spOsobu přípravy týchto zlúčenín.
Je známe, Se dlhoreťazcové organické amoniové soli výkazujú okrem velmi dobrýchpovrchovoaktívnych vlastností aj výrazné biologické účinky. NaSli použitle ako vysoko-účinné dezinfekčné prostriedky v zdravotnickéj praxi, v komunálněj hygienie, vo farmácii,v kozmetike, ale aj v 1'ahkom a ťažkom priemysle.
Popři vysokej dezinfekčněj účinnosti majú vSak aj rad negativných vedlejších účinkovako napr. poměrně vysoků toxicitu a dráždivosť. Preto je snahou modifikovat molekulytakýchto zlúčenín skupinami blízkými organizmu (esterová, amidová, hydroxylová, amino,atň.) a eielom zachovat ich vysokú biologická aktivitu ale znížiť vedlajSie nežiaduceúčinky. V chemickej literatáre boli opísané dialkylestery N,N'-bis(karboxymetyl)-N,N,N',N'--tetrametyléndlamoniumdichloridy, z kterých decylderivát sa používá pod názvom Ethoniumako lokálně anestetikum s antimikrobnym účinkom. NaSiel tiež využitie v analytickej chérail,pri prlprave a úpravě vlastností polymérov, pri elektroforetickom nanáSenl kovov na povrchyz umělých hmOt, v biochémii.
Zlúčeniny, ktoré sú predmetom vynálezu nie sú v chemickej literatáre doteraz opísanéa zistili sa u nich doteraz neznáme bilogické účinky.
Organické amoniové soli sa pripravujú najčastejSie substitučnou nikleofilnou reakcioupříslušných halogénderivátov s terciárnymi amlnmi za rOznych podmienok, pričom výtažkyako aj čistota produktov sú variabilné.
Zlúčeniny, ktoré sú predmetom vynálezu sa připravili reakciou esterov kyseliny brom-octovej β N,N -bisdimetyl-1,2-etándlamlnom v prostředí metylkyanidu pri teplotách 20 až80 °C počas 2 ai 4 h. Výhodou spčsobu podl’a vynálezu je, Se vznikájú produkty takmerv kvantitatívnom výtažku, velmi čisté v poměrně krátkom čase. Připravené soli sú ne-hygroskopické, nižšie homology sú dobré rozpustné vo vodě a polárných rozpúStadlách,nerozpustné v nepolárných rozpúStadlách. Příklad ilustruje vSeobecnú metodu přípravy zlúčenín podlá vynálezu, ktoré sú cha-rakterizované v tabulko. Je uvedená aj antimikrobna aktivita vyjádřená ako minimálnainhibičná koncentrácia (MIC) v /ug.cm“^ resp. mmol.dm-^ na kmene Staphylococcus aureus(s.a.), Escherichia coli (E.c.) a Candida albicans (C.a.). V porovnaní s Ajatlnom (benzyldodecyldimetylaméniumbromid) sú najúčinnejSie zlúčeniny,ktoré sú predmetom vynálezu, účinnejšie na grampozitívne baktérie S. aureus 2-x, na gra-negatívne baktérie E. coli 4-x, aktivita na kvasinky C. albicans je srovnatelná. Okremantimlkróbneho účinku sa stanovila aj povrchová aktivita zo zmien povrchového napštia v závislosti na koncentrácli. V tabulke je uvedená hodnota Y q (zníženie povrchového napatia na medzifázovom roz-hraní voda - vzduch pri kritickéj koncentrácli tvorby miciel C^). sa stanovila aj 3 239430 konduktoawtrieky a straní asien voditoatl v sívialoati na měnách konctntrícle a primárníhodnota a oboch aeraní jo uvedení v tabulko. Taktiet eú uvedení spektrálné cbaraktarlatikyalúCenín, ktorá aú předaňte· vynálesu. Hodnoty a překovej analýay holi v ráaci chybyaetody 10,3 4. Příklad V 30 ca^ aetylkyanidu aa roapuatl 0,1 aol M,N -biadimtyl-1,2-etándiaaínu a pcaaly•a přidá 0,2 aol esteru kyseliny bróaoctovej. Saakcia je exoteraioká a tplota aa aa-aovoXne avýSi a pdvodnýoh 20 na M *C, kde aa udráuje 2 h. Po ochladení a odpaření roa-púátadla aa aíaka produkt, který aa kryitaliaujedo konátantnej teploty topenia ao meaiaceton - aetanol. Ciatota aa okrm překovej analýay, iC-spektier sledovala a) tenkovratevnouchreaatoerafiou (celulóaa) v aúatave butanol - kyselina octová - voda, detekcia Dra<en-dorfovýa Činidla·. 239430 oaot"Omo<woNo^Q0to<o»"O<no^ot»Q£oetOř*^· ·-’·- - — © *- O O <-©>Μ©ΟΙ©Ζ|Α(* o;
- oM J· o«otno(MO^Stf\o*ocMomocJO^o«**or*o^o^oř*dií>t^<noemwoe<^^íno<Qa»oř*o<Mewe*-o ο» a <o < o i o ·- «- — cl o οι 5 01 o ·- m> <h — ·- ·· o ο?δη<η·ί>· - — <9 — ^n^NNONí*· O ř* CM H < © Ol o © © o o *· ·- ©
Ol *? Ol CM Ol
I O I I I © m — ia © < © < © © r> 0*
O h O kf\o m o oOl Ol O Μ,N'-bis/(alkoxykarbonyleetyl)dl»etyl/-1,2-et4ndiasoniuadibroaidy oř* * IA IA ř*
I _ I I Ol I O*OtOJf\O*ON" n « s» * * ·· * Qh m
<M · fl· · ·— · (O · «“ · © · O· · <*3 · ~ «tf\ ♦ ΙΑ I moioiir\mooiotrttf\<nooi<mr*w\< φφ ·- ·- Ol — οι <n π i i i l o o o t* o
Ol ΓΠ — . S-
Ol
Ol m Ol m σ* ~ 9 • o «- 9 01 O o CA 9* • r- Ol 01 9 < © «» m o <n o i — 1 o 1 *· <n © ΓΊ <n O Ol o m © <*> — 1 Ol 0- Ol 0- Ol 0* Ol Ol Ol Ol 0- 01 0- Ol 0- Ol 0- Ol (* Ol 0- Ol r* Ol Ο^'ύΟΠβΟΟΟΠΝΟΡίί'ΟίΛΝβ’-ΐΑβίΛΐη’-ΟίΛΟβΙ 4oix^<*(nwooi'<oj*»-(*>’-<*’*»-n*’tOJ<»-'í^ oir*-oit*oih-oiř*oif*oit*-oiř*oit*oiř*oit^oi(*oiř-oit*oio- 9<Μ«>*9*Α9*··9<η·οι© — © ia ία o < o οι iř\ <a
SO ř- 8 r- S>
Sk ·» « Sk· Sk Sk φ> Sk Sk ^ο^οΐΑο^*ο9©©©«η©^οο*ο^<A Ch 9i Ot Ch CA. 0* CA CA ¢0 \0 \0 © vo <*> 0*
IA Ol lA IA IA 0- » © * 0- 0- \o «· < *· < < < K0 © 0- t* IA 0- 0· 0- >M OJ 0 0 0 M w M >M »H >tt >N *3 0 0 0 0 ia IA 0 0 IA 0 IA 0 IA © © ia w- < n OJ < VO IA \0 0- VO ia vo © 0- (- 0- 0- 0» 0- 0- OJ s i o 3
P 7 s
A l> 0
JA * rH řř H >> 0 >» P £ H P M H ►> p4 44 O ►s •M rH P >i O « P >5 >> O. P O O 0 0 O 0 44 0 Φ 1 O 0 A 0 •H 0 Ol 0 Ό
H >>
O 0 Ό H >> H H P S >> rH 0 O 0 ►> Λ H 0 0 O • fe Ό *0 0 0 o 0 0 Ό b Φ »4 P 0 0 •0 P 0 H P O 0 0 Φ 1 Ό P O. X! ft o T3 §
239430 2
The present invention relates to H, N'-bia [(alkoxycarbonyl) dimethyl] -1,2-ethanediammonium dibromides of the general formula
wherein R is a linear or branched alkyl chain and a number of carbon atoms of 6 to 16 or p-tert-butylphenyl and a process for preparing such compounds.
It is known that, in addition to very good surface-active properties, long-chain organic ammonium salts also exhibit significant biological effects. NaSli has been used as a highly effective disinfectant in medical practice, in community hygiene, in pharmacy, in cosmetics, but also in the industry and in the heavy industry.
However, in addition to the high disinfection efficiency, a number of negative side effects, such as relatively high toxicity and irritability, have also been reported. Therefore, it is desirable to modify the molecules of such compounds by groups close to the organism (ester, amide, hydroxyl, amino, etc.) to maintain their high biological activity but to reduce the side-effects. In the chemical literature, dialkyl esters of N, N'-bis (carboxymethyl) -N, N, N ', N' - tetramethylenedlammonium dichlorides have been described, of which the decyl derivative is used under the name Ethonium as a topical anesthetic with antimicrobial activity. It has also been used in analytical chemistry, in the preparation and conditioning of polymers, in the electrophoretic deposition of metals on the surface of artificial plastics, in biochemistry.
The compounds of the invention not previously described in the chemical literature have been found to have no known biological effects.
The organic ammonium salts are most often prepared by the substitution nickelophilic reaction of the respective halogenated derivatives with tertiary amines under different conditions, and the product purity is variable.
The compounds of the present invention were prepared by reacting bromoacetic acid esters with N, N-bis-dimethyl-1,2-ethanediamine in methyl cyanide at 20 to 80 ° C for 2 to 4 hours. the products of takmerv are produced quantitatively, very clean in a relatively short time. The salts prepared are non-hygroscopic, the lower homologues are good water-soluble and polar solvents insoluble in non-polar solvents. The example illustrates a general method for preparing compounds of the invention which are characterized in a table. Antimicrobial activity, expressed as minimal inhibitory concentration (MIC) in /ug.cm, is also shown. mmol.dm- to strains of Staphylococcus aureus (sa), Escherichia coli (Ec) and Candida albicans (Ca). Compared to Ajatl (benzyldodecyldimethylammonium bromide), the most effective compounds of the present invention are more potent on Gram-positive bacteria S. aureus 2-x, on negative E. coli bacteria 4-x, the activity on C. albicans is comparable. In addition to the antimicrobial effect, surface activity was also determined from surface tension changes in a concentration-dependent manner. In the table, the value of Y q (reduction of surface tension at the interfacial extent of water-air at critical concentration of formation of micelles) is shown. 3 239430 Conductoawrots were also determined and the Asien voditoatl in sivialoati on currencies and primary value, and both aerani yo were listed in the table. Taktiet eu introduction of spectral cbaractarlatikyalúCénin, which to transmit. Values and overhang analysis of the rod at error 10,3 4. Example V of 30 c a-ethyl cyanide and roapuatl of 0.1 aol of M, N-biadimtyl-1,2-ethanediaine and add and add 0.2 aol of bromoacetic acid ester. The reaction is exothermic and aa and aa-avoxy and 20 to M < + > C, where aa is measured for 2 hours. After cooling and evaporation of the roating agent and any product which has a constant melting point and acetone-acetone. Cotaota and a cross-over analysis, iC-spectra followed by a) thin-cell chromatography (cellulose) in butanol-acetic acid-water, detection of Dra-enorphine reagent. 239430 oaot "Omo <woNo ^ Q0to <o» "O <no ^ ot» Q £ oetOr * ^ · · - '- - - © * - OO <- ©> © ΟΙ © Ζ | Α (* o;
- oM J · o «otno (MO ^ Stf o * ocMomocJO ^ o« ** or * o ^ o ^ oí * dií> t ^ <noemwoe <^^ íno <Qa »oř * o <Mewe * -o ο »A <o <oio · -« - - cl o οι 5 01 o · - m><h - · - ·· o ο? Δη <η · ί> · - - <9 - ^ n ^ NNON * * O * H H <<oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo oo ©
Ol *? Ol CM Ol
IOIII © m © Ã © ©
OO, O, O, N'-bis / (alkoxycarbonylethyl) d1 ethyl / 1,2-ethanedioic diadibroaids IA IA *
I _ II Ol IO * O * ON "n« s »* * ·· * Qh m
M “· I O O · * I I I I I I I I I I I I I I I I I I I I I I I I I - - - οι <n π iiilooot * o
Ol ΓΠ -. WITH-
Ol
Ol m Ol σ * ~ 9 • o «- 9 01 O o CA 9 * • r- Ol 01 9 <©« »mo <noi - 1 o 1 * · <n © n <n Ol Ol © <* Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol Ol ΟΠβΟΟΟΠΝΟΡίί'ΟίΛΝβ'-βΑβίΛΐη'-oίΛΟβΙ 4oix ^ <* (nwooi '<oj * »- (*>' - <* '*» - n *' OJ <»- 'i ^ oir * -oit * oih-oiř * oif * oit * -oi * oit * oiř * oit ^ oi (* oiř-oit * oio- 9 <Μ «> * 9 * Α9 * ·· 9 <η · οι © - © ia o <o οι iř \ t
SO ø- 8 r- S>
Sk · «Sk φ Sk φ Sk ^ ο ο ο ο Ch Ch Ch Ch Ch Ch Ch Ch Ch Ch Ch Ch 9 9 9 9 9 0 * CA CA ¢ 0 \ t
IA Ol lA IA IA 0- »© * 0- 0- 0 0 0 0 0 0 0 0 0 M 0 M 0 H 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0- OJ sio 3
P 7 s
A l> 0
Y * rH ø H >>0> »P £ HPMH ►> p4 44 O ►s • M rH P> i O« P> 5 >> O. POO 0 0 O 0 44 0 Φ 1 O 0 A 0 • H 0 Ol 0 Ό
H >>
O 0 Ό H >> HHPS >> rH 0 O 0 ►> Λ H 0 0 O • fe Ό * 0 0 0 0 0 0 Ό b Φ »4 P 0 0 • 0 P 0 HPO 0 0 Φ 1 Ό P O X! ft o T3 §
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS355384A1 CS355384A1 (en) | 1985-05-15 |
| CS239430B1 true CS239430B1 (en) | 1986-01-16 |
Family
ID=5375945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS239430B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0427224A1 (en) * | 1989-11-08 | 1991-05-15 | Kao Corporation | Novel polycationic compound and bleach composition containing the same |
-
1984
- 1984-05-14 CS CS843553A patent/CS239430B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0427224A1 (en) * | 1989-11-08 | 1991-05-15 | Kao Corporation | Novel polycationic compound and bleach composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CS355384A1 (en) | 1985-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0038192B1 (en) | 5-alkylsalicylanilides derivatives and method for inhibiting the growth of microorganisms | |
| FI60020C (en) | SOM HERBICID ANVAENDBART 2-CARBOXYTHYL-N-PHOSPHONOMETHYLGLYCINATE OCH DESS SALTER | |
| US4542023A (en) | Fungicidal salts of organophosphorus derivatives | |
| US4608368A (en) | 1-hydroxy-1,1-diphosphonic acids and cytostatic use thereof | |
| US5206386A (en) | Controlled release N-substituted pyrrolidone esters and process for the use thereof | |
| KR20010070962A (en) | Phosphorous organic compounds and their use | |
| ES8502126A1 (en) | Milbemycin D derivatives, their preparation and compositions containing them. | |
| CS239430B1 (en) | N-n-bis//alkoxacarbonylmethyl/dimethyl/-1,2-ethandiamonium dibromides and method of theier preparation | |
| KR19990025064A (en) | Quaternary Ammonium Phosphate Compounds and Manufacturing Method Thereof | |
| KR19980018872A (en) | Disinfectant | |
| OZAWA et al. | Synthesis and antimicrobial activity of salicylanilide derivatives. II | |
| US4108990A (en) | Method of killing bacteria and fungi | |
| FI67856C (en) | FOERFARANDE FOER FRAMSTAELLNING AV ETT ANTIBAKTERIELLT SILVERSALT AV FOSFANILSYRA | |
| WO2008091182A2 (en) | Anti-infective agent production methods | |
| US4965395A (en) | P-oxybenzoic acid compounds | |
| Samota et al. | Synthesis, characterization, and biological activity of organophosphates derived from substituted benzoxazole | |
| FI59803B (en) | FRAMEWORK FOR THE PURPOSE OF THERAPEUTIC ANALYZED PENICILLANSYRADERIVATER | |
| US3597451A (en) | Process for the preparation of (+) cis-1,2-epoxypropyl)-phosphonic acid and derivatives | |
| SU360733A1 (en) | ||
| FI75576C (en) | GUIDELINES AMINOFOSFONSYRAFOERENINGAR, DERAS FRAMSTAELLNING OCH ANVAENDNING SAMT I FOERFARANDET ANVAENDBARA MELLANPRODUKTER. | |
| EP0156729A2 (en) | Inner salts of phosphonic acid useful in the protection of plants from pathogenesis caused by fungi | |
| SU606317A1 (en) | Trinitrophenylphosphonates possessing bactericidic and fungicidic activities and their preparing method | |
| JPH05331057A (en) | Fungicide | |
| CS277139B6 (en) | N-|2-(undecenoylamino)ethyl¨-n,n,n-alkyl dimethylammonium bromides and process for preparing thereof | |
| CN1202107C (en) | 2-(4-methiophnoxy)-5-furfural imidazolone derivative with bactericiding activity |