CS276062B6 - Alkoxyphenylcarbamic acid dimethylaminoethyl ether aliphatic agent - Google Patents
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Abstract
Algicídny prostriedok, ktorý ako účinnú látku obsahuje zlúčeninu obecného vzoirca I kde OR znamená alkoxyl a 1 až 10 atornami uhlíka v orto-, meta- alebo para-polohe benzénového jadra. NHC00CH2CH2N(CH3)2 © 01© Příprava těchto novoayntetizovaných , zlúčenin je popísaná v práci autorovi ■ Čižmárik J., Mitošinková M., Borovanský A., Švec P.í Pharmazie 33. 509 /1978/. Zlúčeniny posoblagalgicídna pri koncentráclách 4,5.10"° mol.dm"-’ a vyšších /t.j. pri koncentráclách 1,6 mg.dm"-5 a vyšších/.Algicidal agent, which contains as an active substance a compound of the general formula I where OR means alkoxyl and 1 to 10 carbon atoms in the ortho-, meta- or para-position of the benzene nucleus. NHC00CH2CH2N(CH3)2 © 01© The preparation of these newly synthesized compounds is described in the work of the author ■ Čižmárik J., Mitošinková M., Borovanský A., Švec P.í Pharmazie 33. 509 /1978/. The compounds are effective against algae at concentrations of 4.5.10"° mol.dm"-' and higher /i.e. at concentrations of 1.6 mg.dm"-5 and higher/.
Description
CS 276062 B6
Vynález es týká algicídneho prostriedku, ktorý ako účinnú látku obsahuje zlúče-ninu obecného vzorca I
II i IIH000CII2CII2II(CII3)2Θ
Cl' /1/ kde OR znamená alkoxyl s 1 až 10 atómami uhlíka v orto-, meta- alebo para- polohebenzénového jadra. Údaje vztahujúce sa na přípravu novosyntetizovaných zlúčenín podlá obecnéhovzorca I aú obslahnuté v prácach autorov: Čižtnárik J,, Borovanský A., Švec P.:
Acta Fac. Pharmac. Univ. Comenlanae, 29.53/1976/ a Čižtnárik J., Mitošinková M.,Borovanský A., Švec P. s Pharmazle 33. 509/1978/. Tieto zlúčeniny vykazujú lokálněanestetickú účinnost*.
Prl íaleom Studiu biologlckej účinnosti zlúčenín obecného vzorca I sme zlatili,že tieto výrazné inhibujú rast a syntézu chlorofylu rias.
Inhibičná účinnost1 zlúčenín obecného vzorca I na rlasy sa testovala stacionámoukultiváciou synchrónnej kultúry rias Chlorella vulgaris. Hodnotil sa nárast buniekrias, ako aj obsah syntetizovaného chlorofylu. Podrobný popis metody hodnotenia jeuvedený v příklade 1. Miera antialgálnej účinnosti zlúčenín obecného vzorca I je vy-jádřená údajmi v tab, 1. Inhibičný vplyv na riasy sa sledoval u následujúcich zlúče-nín obecného vzorca 1: I. Ií-[2-(2»metoxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid III. H-[2-(4-metoxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid IV. H-j2-(2-etoxyfenylkarbamoyloxy)-etyrj-dimetylamóniumchlorid V. N- [£-(3-etoxyfenylkarbanoyloxy)-etylJ-dimetylamóniumchlorid VI. N- [2-(4-etoxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid VII. ΒΓ-^-(2-propoxyfenylkarbamoyloxy)-etyl?-dimetylamóniumchlorid VIII. N-^-(3-propoxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid IX. N- J2-(4-propoxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid X. N-[2-(2-butoxyfenylkarbameyloxy)-etyí] -dimetylamóniumchlorid XI. N-j2-(3-butoxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid XII. N- |2-(4-butoxyfenylkarbamoyloxyJ-etylJ -dimetylamóniumchlorid XIII. N-j2-(2-pentyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid XIV. N- [2-(3-pentyloxyfenylkarbamoyloxy)-etyl] -dimetylamóniumchlorid XV. H-^-(4-pentyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid XVI. N-|p-(2-hexyloxyfenylkarbamoyloxy)-etyl] -dimetylamóniumchlorid XVII. ΪΓ-j2-(3-hexyloxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid XVIII. N-jž-(4-hexyloxyíenylkarbamoyloxy)-etyl]-dimetylamóniumchlorid XIX. UT-^2-(2-heptyloxyfenylkarbamoyloxy)-etyl3-dimetylamóniumchlorid XX. N- £?-(3-heptyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid XXI. N- £2-(4-heptyloxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid XXII. N-Í2-(2-oktyloxyfenylkarbamoyloxy)-etyl] -dimetylamóniumchlorid XXIV. N-Í2-(4-oktyloxyfenylkarbemoyloxy)-etylJ -dimetylamóniumchlorid XXV. N- {2-(2-nonyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid XXVI. ÍT- [2-(3-nonyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid CS 276062 B6 XXVIII. N“ [2-(2-decyloxyfenylkarbamoyloxy)-etylJ-dimetylamóniumchlorid XXIX. N-j2-(3-decyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid XXX. H- [2-(4-decyloxyfenylkarbamoyloxy)-etylJ -dimetylamóniumchlorid
Tabuťka 1
Inhibičná účinnost1 látok obecného vzorca I na riasy Chlorella vulgaris Látka IC50 syntézy chlorofylu MIC syntézy chlorofylu IC5Q 10"6 mól.dm"3 rastu rias I 158,5 500,0 100,0 III 90,8 363,0 281,8 IV 112,2 275,4 190,5 V 75,9 166,0 91,8 VI 46,8 151,4 53,1 VII 83,2 302,0 156,6 VIII 31,6 75,9 45,7 IX 22,9 50,0 29,5 X 75,9 109,6 55,0 XI 23,4 50,0 55,0 XII 11,0 25,1 12,0 XIII 27,5 5.7,5 32,7 XIV 11,0 25,0 12,5 XV 9,5 25,0 13,2 XVI 13,8 46,7 24,0 XVII 5,8 9,1 6,6 XVIII 5,6 12,6 7,2 XIX 6,3 7,6 7,1 XX 2,1 4,5 2,5 XXI 4,0 5,0 4,5 XXII 5,9 7,6 4,4 XXIV 5,5 11,7 5,6 XXV 5,8 7,6 6,3 XXVI 5,9 6,3 6,3 XXVIII 5,3 6,3 6,3 XXIX 4,5 33,1 10,2 XXX 4,1 72,4 4,4 IC,j0 značí koncentráciu Studovanej látky, pri ktorej dochádza k 50%nej inhibíciibodnotneného parametre rias vzhladom na kontrolně vzorky MIC značí minimálnu koncentráciu Studovanej látky, pri ktorej dochádza k upínej in-hibícii hodnoteného parametre rias.
Nasledujúci příklad bližSie osvětluje inhiblčnú účinnost' zlúčenín podlá vynále-zu na zelené riasy.
I 3 CS 276062 B6 Příklad 1 Účinek zlúčenín podlá vynálezu na rast rias Chlorella vulgaris a obsah syntetizova-ného chlorofylu
Riasy Chlorella vulgaris se pěstovali stacionémou kultlváciou prl teplotě25+1 °C, prl svetelnom režime 16 hodin světlo - 8 hodin tma, v kultlvačnom médiupodlá Šetlika /Šetlík I.: Annual Report of Algolog lab. for 1967, 71-140, Třeboň,1968/. K živnému médiu sa přidával roztok študovanej zlúčeniny v destilovanej vodětakej koncentrácie, aby sa získala série kultlvačnýcb banlek s odstupňovanou končen-tráciou látky a odstrupňovaným biologickým účinkom. Banky sa inokulovali přesnýmobjemem homogénnej suspenzie rias. Po 7-dennej kultlvácil sa objem kultlvačného médiadoplnil destilovanou vodou na povodný objem /vyrovnanle odpáru vody/ a v suspendiibuniek sa merala absorbancla pri 660 nm /úměrná množstvu bunlek rias/ a obsah chloro-fylu po jeho extrakci! dimetylformamidom z odcentrifugováných bunlek rias. Celkovýobsah chlorofylu rias v kultlvačnom médiu se vyhodnotil podťa rovnice:
Chl /mg.dm“3/ a 17,9 Αθ^γ + Agg^ . 8,06, kde A je absorbancla vzorky pri 647, resp. 664,5 nm v 1 cm kývete /Inskeep W.P., Bloom P.R.: Plant Physiol. 77/2/. 483-5, 1985/. Získané hodnoty týchto parametrov sa porovnávali s hodnotami parametrov kontrol-ných vzoriek /vyhodnotené ako % kontroly/. Ba základe týchto hodnot sa extrapoláclouvyčíslili koncentrácie Studovaných zlúčenín, pri ktorých sa dosiahla 50%ná inhibícia/ΙΟ^θ/ a v případe hodnot chlorofylu aj úplná inhibícia /MIC/. Z hodnot absorbanciesa MIC nevyhodnocovala, nakoíko touto metodou sa stanovujú tlež odfarbené mrtvébuňky rias, a teda aj pri úplnej inhlbícli sa namerajú určité hodnoty absorbancie.
Například v případe testovanla účinku zlúčeniny XIV sa k 12 ml kultlvačného mé-dia a inokulom rias přidalo 0,12 ml vodného roztoku zlúčeniny XIV nasledovných kon-centrácií: 2.5.1Ο"3, l,25.1O”3, 9,0.10-4 a 7.5.1Ο"4 mól.dm"3.
Skutočné koncentrácie zlúčeniny XIV v kultlvačnom médiu a příslušné hodnoty inhibí-cie rastu rias a syntézy chlorofylu, vyjádřené v % kontrolných vzoriek sú uvedenév tab. 2.
Hodnoty koncentrácie študovanej zlúčeniny, pri ktorej dochádza k 50%nej, resp.úplnej inhlbícli študovaného parametre rias sa zistuje extrapoláclou zo závislostivyššie uvedených hodnot % zlstenej inhibícia sledovaného parametra od logaritmu apli-kované j koncentrácie študovanej zlúčeniny.
Tabuťka 2
Inhibícia rastu rias a syntézy chlorofylu v přítomnosti zlúčeniny XIV
Konc.zlúč.XIV 10"6 mól.dm"3 % kontroly + Chlorofyl Absorbancla 25,0 0 21,6 + 1,2 12,5 43,6 + 2,5 50,1 + 2,7 9,0 77,2 + 4,8 86,1 + 2,5 7,5 80,6 + 0,7 91,5 + 4,3 (3 - smerodajná odchýlka
CS 276062 B6
The invention relates to an algicidal composition which comprises as active ingredient a compound of formula I
II i IIH000CII2CII2II (CII3) 2Θ
Cl '(1) wherein OR is a C 1 -C 10 alkoxy in the ortho, meta- or para- position of the benzene ring. Data related to the preparation of the newly synthesized compounds according to general formula I and are included in the works of the authors: Čižtnárik J ,, Borovanský A., Švec P .:
Acta Fac. Pharmac. Univ. Comenlanae, 29.53 (1976) and Čižtnárik J., Mitošinková M., A. Borovanský, and Švec P. with Pharmazle 33. 509 (1978). These compounds exhibit local anesthetic efficacy *.
A further study of the biological efficacy of the compounds of formula (I) was that these marked inhibition of the growth and synthesis of algal chlorophyll.
The inhibitory activity of the compounds of the formula I on the rash was tested by stationary culture of the synchronous algal culture Chlorella vulgaris. The growth of cell lines as well as the content of chlorophyll synthesized was evaluated. A detailed description of the evaluation method given in Example 1. The level of anti-algal efficacy of the compounds of formula I is shown in Table 1. The algae inhibitory effect was followed for the following compounds of formula 1: I.I- [2- (2 Methoxyphenylcarbamoyloxy) ethylJ-dimethylammonium chloride III. H- [2- (4-methoxyphenylcarbamoyloxy) ethyl] -dimethylammonium chloride IV. N- [2- (2-ethoxyphenylcarbamoyloxy) -ethoxy] -dimethylammonium chloride V. N - [(3-Ethoxyphenylcarbanoyloxy) ethyl] dimethylammonium chloride VI. N- [2- (4-Ethoxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride VII. N- [2- (2-propoxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride VIII. N - [(3-propoxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride IX. N- [2- (4-propoxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride X. N- [2- (2-butoxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride XI. N-2- (3-butoxyphenylcarbamoyloxy) ethyl-dimethylammonium chloride XII. N- [2- (4-butoxyphenylcarbamoyloxy] ethyl] -dimethylammonium chloride, XIII, N-2- (2-pentyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride, XIV, N- [2- (3-pentyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride, - (4-pentyloxyphenylcarbamoyloxy) ethyl-dimethylammonium chloride XVI. N- [beta] - (2-Hexyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride XVII. N-2- (2-heptyloxyphenylcarbamoyloxy) -ethyl-3-dimethylammonium chloride N-N - (3-Heptyloxyphenylcarbamoyloxy) -ethyl-N-dimethylammonium chloride XIX-N-2- (4- N, N '-( 4-octyloxyphenylcarbemoyloxy) ethyl] -dimethylammonium chloride XXV, N - {2- (2-nonyloxyphenylcarbamoyloxy) - ethyl-dimethylammonium chloride XXVI, N- [2- (3-nonyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride CS XXVIII, N '[2- (2-decyloxyphenylcarbamoyloxy) ethyl] -dimethylammonium chloride XXIX, N 2 - (3-decyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride XXX. H- [2- (4-decyloxyphenylcarbamoyloxy) ethyl] dimethylammonium chloride
Tabuťka 1
Inhibitory activity of compounds of formula I on Chlorella vulgaris algae Substance IC50 of chlorophyll synthesis MIC chlorophyll synthesis IC5Q 10 "6 mol.dm" 3 algae growth I 158.5 500.0 100.0 III 90.8 363.0 281.8 IV 112 , 2,275.4 190.5 V 75.9 166.0 91.8 VI 46.8 151.4 53.1 VII 83.2 302.0 156.6 VIII 31.6 75.9 45.7 IX 22 , 9 50.0 29.5 X 75.9 109.6 55.0 XI 23.4 50.0 55.0 XII 11.0 25.1 12.0 XIII 27.5 5.7.5 32.7 XIV 11 , 0 25.0 12.5 XV 9.5 25.0 13.2 XVI 13.8 46.7 24.0 XVII 5.8 9.1 6.6 XVIII 5.6 12.6 7.2 XIX 6 , 3 7.6 7.1 XX 2.1 4.5 2.5 XXI 4.0 5.0 4.5 XXII 5.9 7.6 4.4 XXIV 5.5 11.7 5.6 XXV 5 , 8 7.6 6.3 XXVI 5.9 6.3 6.3 XXVIII 5.3 6.3 6.3 XXIX 4.5 33.1 10.2 XXX 4.1 72.4 4.4 IC, is the concentration of the study substance at which 50% of the inhibited algal parameter occurs with respect to the MIC control means the minimum concentration of the study substance at which the algae parameter being evaluated is clamped.
The following example illustrates the green algae inhibitory activity of the compounds of the invention.
Example 1 Effect of the compounds of the invention on the growth of algae Chlorella vulgaris and the content of synthesized chlorophyll
Algae Chlorella vulgaris was grown by stationary culture at a temperature of 25 + 1 ° C, a light regime of 16 hours light - 8 hours darkness, in a culture medium by Šetlika / Šetlík I .: Annual Report of Algolog lab. for 1967, 71-140, Trebon, 1968 /. To the nutrient medium, a solution of the study compound in distilled aqueous concentration was added in order to obtain a series of culture flasks with graded substance concentration and sheared biological effect. The flasks were inoculated with a precise volume of homogeneous algae suspension. After a 7-day culture, the volume of culture medium was filled with distilled water to a volume of water / equal to water evaporation, and absorbance at 660 nm / proportional to the amount of algae cells and chlorophyll content after extraction was measured in the suspension cells. dimethylformamide from centrifuged algal cells. The total content of chlorophyll algae in the culture medium was evaluated by the equation:
Chl /mg.dm"3/ and 17.9 Αθ ^ γ + Agg ^. 8.06, where A is the absorbance of the sample at 647 and 647 respectively. 664.5 nm in 1 cm swing / Inskeep WP, Bloom PR: Plant Physiol. 77/2 /. 483-5 (1985). The values obtained for these parameters were compared with the control parameter values (evaluated as% control). Based on these values, the concentrations of the study compounds at which 50% inhibition (ΙΟ ^ θ) and, in the case of chlorophyll values, complete inhibition (MIC), were also extrapolated. It did not evaluate the absorbance values of the MIC, since this method also determines the bleached dead algae cells, and therefore, even with a full inhibition, certain absorbance values are measured.
For example, in the case of testing the effect of compound XIV, 0.12 ml of an aqueous solution of compound XIV of the following concentrations was added to 12 ml of culture medium and algae inoculum: 2.5.1- " 3.1, 25.1 " and 7.5.1Ο "4 mole.dm" 3.
The actual concentrations of Compound XIV in the culture medium and the respective algal growth and chlorophyll synthesis inhibition values, expressed as a percentage of the control samples, are shown in Tab. 2.
The concentration of the study compound at which 50% and / or complete inhibition of the algal parameter studied is found is extrapolated from the dependence of the% inhibition of the observed parameter on the logarithm of the applied compound concentration.
Tabuťka 2
Inhibition of algal growth and chlorophyll synthesis in the presence of compound XIV
End-end XIV 10 "6 mole.dm" 3% control + Chlorophyll Absorbancla 25.0 0 21.6 + 1.2 12.5 43.6 + 2.5 50.1 + 2.7 9.0 77 , 2 + 4,8 86,1 + 2,5 7,5 80,6 + 0,7 91,5 + 4,3 (3 - standard deviation
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| Application Number | Priority Date | Filing Date | Title |
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| CS903477A CS276062B6 (en) | 1990-07-13 | 1990-07-13 | Alkoxyphenylcarbamic acid dimethylaminoethyl ether aliphatic agent |
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| Application Number | Priority Date | Filing Date | Title |
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| CS903477A CS276062B6 (en) | 1990-07-13 | 1990-07-13 | Alkoxyphenylcarbamic acid dimethylaminoethyl ether aliphatic agent |
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| Publication Number | Publication Date |
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| CS347790A3 CS347790A3 (en) | 1992-01-15 |
| CS276062B6 true CS276062B6 (en) | 1992-03-18 |
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