CS276061B6 - Alkoxyphenylcarbamic acid pyrrolidinoethyl esters - Google Patents
Alkoxyphenylcarbamic acid pyrrolidinoethyl esters Download PDFInfo
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Abstract
Algicídny prostriedok, ktorý ako účinnú látku obsahuje zlúčeninu obecného vzorca I kde OR znamená alkoxyl s 1 až 7 atornami uhlíka v orto-, meta- alebo para- polobe benzónového jadra. Principy přípravy týchto novosyntetizovaných zlúcenín sú popísanév práci autorov: Cižmárik J., Borovanský A., Švec P.; Acta Fac.Pharm. Univ. Comeniane, XXIX, 53, 1976. Zlúčeniny posobiaalgieídne..prl koncentráciách 1,45.10-5 mol.dm"·7 /t.j, 5,4 mg.dm"·7/ a vyšších.Algicidal agent, which contains as an active substance a compound of the general formula I where OR means alkoxyl with 1 to 7 carbon atoms in the ortho-, meta- or para- side of the benzoic nucleus. The principles of preparation of these newly synthesized compounds are described in the work of the authors: Cižmárik J., Borovanský A., Švec P.; Acta Fac.Pharm. Univ. Comeniane, XXIX, 53, 1976. The compounds are algicidal at concentrations of 1.45.10-5 mol.dm"·7 /i.e., 5.4 mg.dm"·7/ and higher.
Description
1 CS 276061 B6
Vynález sa týká alfcicídneho prostriedku, ktorý ako účinnú látku obsahuje zlúče-ninu podlá obecného vzorca I
kde OR znamená alkoxyl β 1 až 7 atornami uhlíka v orto-, meta- alebo para- polohebenzánového jadra.
Principy přípravy týchto novosyntetizovaných zlúčenín sú popísané v práci auto-rov Čižmárik J., Borovanský A., Šveo P.: Acta Pac.Pharm. Univ.Comeniane XXIX,53»1976/.
Pri cíalšom atúdiu biologickej účinnosti zlúčenín obecného vzorca I sme zistili,že tieto výrazné inhibujú rast a syntézu chlorofylu rlas.
Inbiblčná účinnost1 zlúčenín obecného vzorca I na riasy sa testovala stacionář-nou kultiváciou synchrónnej kultury rias Chlorella vulgaris. Hodnotil sa nárast bu-niek rias, ako aj obsah syntetizovaného chlorofylu. Podrobný popis metody hodnoteniaje uvedený v příklade 1, Miera antialgálnej účinnosti zlúčenín obecného vzorca I jevyjádřená údajmi v tab. 1. Inhibičný vplyv na riasy sa sledoval u nasledujúcich zlú-čenín obecného vzorca I: I. N-^2-(2-metoxyfenylkarbamoyloxy)-etylJ-pyrolidíniumchlorid II. N- /2-(3-metoxyfenylkarbamoyloxy)-etyl]-pyrolidíniumchlorid III. N-Í2-(4-metoxyfenylkarbamoyloxy)-etyl]-pyrolidíniumchlorid IV. N-j2-(2-etoxyfenylkarbamoyloxy)-etylJ-pyrolidíniumchlorid V. N-^-(3-etoxyfenylkarbamoyloxy)-etyl}-pyrolidíniumchlorid VI. N- ^-(4-etoxyfenylkarbamoyloxy)-etylJ-pyrolidíniumcblorid VII. N-^-(3-propoxyfenylkarbamoyloxy)-etylJ -pyrolidíniumchlorid VIII. N-^-(4-propoxyfenylkarbamoyloxy)-etyý-pyrolidíniumchlorid IX. N- [2-(2-butoxyfenylkarbamoyloxy)-etylJ -pyrolidíniumchlorid X. N- ^-(3-butoxyfenylkarbamoyloxy)-etylJ-pyrolidíniumchlorid XI. H- [2-(4-butoxyfenylkarbamoyloxy)-etylJ -pyrolidíniumchlorid XII. N-^2-(2-pentyloxyfenylkarbamoyloxy)-etyť/-pyrolidíniumchlorid XIII. N- g-(4-hexyloxyfenylkarbamoyloxy)-etyl]-pyrolidíniumchlorid XIV. N- |2-(2-heptyloxyfenylkarbamoyloxy)-etyl7-pyrolidíniumchlorid XV. N-j2-(4-heptyloxyfenylkarbamoyloxy)-etylj -pyrolidíniumchlorid
Tabuťka 1
Inhibičná účinnost’ látok obecného vzorca I na riasy Chlorella vulgaris CS 276061 B6 Látka IC50 syntézy chlorofylu MIC syntézy chlorofylu Ι05θ 10"6 mól.dm-3 rastu rlas I 49,0 234,0 91,6 II 26,9 200,0 44,6 III 15,1 57,5 21,4 IV 61,7 25,1 83,2 V 25,7 61,7 34,7 VI 22,9 50,0 29,5 VII 11,5 26,3 17,8 VIII 9,3 25,1 13,8 IX 26,9 51,3 34,7 X 13,8 25,1 27,5 XI 9,1 25,1 10,0 XII 18,6 28,2 23,4 XIII 9,3 14,5 10,0 XIV 8,7 18,2 10,0 XV 10,0 17,4 11,2 IC^q značí koncentráclu Študovanej látky, pri ktorej dochádza k 50%nej inhibíciihodnoteného parametra rias vzhladom na kontrolně vzorky. MIC značí minimálnu koncentráclu študovanej látky, pri ktorej dochádza k upínejlnhibícli hodnoteného parametra rlas.
Nasledujúci příklad bližšie osvětluje lnhlbičnú účinnost' zlúčenín podlá vyná-lezu na zelené riasy. Příklad 1 Účinok zlúčenín podťa vynálezu na rast rlas Chlorella vulgaris a obsah syntetizova-ného chlorofylu
Riasy Chlorella vulgaris sa pěstovala staclonáraou kult i vádou pri teplote25 + 1 °C, prl svetelnom režime 16 hodin světlo -8 hodin tma, v kultlvačnom médiupodlá Šetlíka /šetlík I.: Annual Report of Algolog.Lab. for 1967, 71-140, Třeboň,1968/. K živnému médiu sa přidával roztok študovanej zlúčenlny v destllovanej vodětakej koncentrácie, aby sa získala séria kultlvačných baniek a odstupňované^ koncen-tráclou látky a odstupňovaným biologickým účlnkom. Banky sa inokulovali přesným ob-jemem homogénnej suspenzie rlas. Po 7-dennej kultlvácii sa objem kultivačného médiadoplnil destilovanou vodou na povodný objem /vyrovnanie odparu vody/ a v suspenzi!buniek sa merala absorbancla při 660 nm /úměrná množstvu buniek rlas/ a obsah chlo-rofylu po jeho extrakci! dimetylformamidom z odcentrifugováných buniek rlas. Celkovýobsah chlorofylu rias v kultlvačnom médiu sa vyhodnotil podlá rovnice:
Chl/mg.dm“^/ 17,9 Ag4? +8,08 Agg4 kde A je absorbancla vzorky pri 647, resp. 664,5 nm v 1 cm kývete /Inskeep W.P., Bloom P.R.: Plant Physlol. 77/2/. 483-5, 1985/
1 CS 276061 B6
The present invention relates to an alcicidal composition which comprises as active ingredient a compound of the formula I
wherein OR represents an alkoxy β of 1-7 carbon atoms in the ortho-, meta-, or para-benzobenzene ring.
The principles of preparation of these newly synthesized compounds are described in the work of Čižmárik J., Borovanský A., Šveo P .: Acta Pac.Pharm. Univ.Comeniane XXIX, 53 (1976).
In a more thorough assessment of the biological activity of the compounds of formula I, we have found that these markedly inhibit the growth and synthesis of chlorophyll rlas.
Inhibitory activity of the compounds of formula I on algae was tested by stationary cultivation of the synchronous algal culture Chlorella vulgaris. The growth of algal cells as well as the content of chlorophyll synthesized were evaluated. A detailed description of the evaluation method is given in Example 1, and the degree of anti-algal efficacy of the compounds of Formula I is shown in Table 1. 1. The algae inhibitory effect of the following compounds of formula I was followed: I. N- [2- (2-methoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride II. N- [2- (3-methoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride III. N 2 - (4-methoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride IV. N- [2- (2-ethoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride V. N- (3-ethoxyphenylcarbamoyloxy) ethyl} pyrrolidinium chloride VI. N- [4- (4-ethoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride VII. N - [(3-propoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride VIII. N - [4- (4-propoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride IX. N- [2- (2-butoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride X. N- (3-butoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride XI. H- [2- (4-butoxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride XII. N- [2- (2-pentyloxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride XIII. N - (4-Hexyloxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride XIV. N- [2- (2-heptyloxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride XV. N - [2- (4-heptyloxyphenylcarbamoyloxy) ethyl] pyrrolidinium chloride
Tabuťka 1
Inhibitory activity of compounds of formula I on Chlorella vulgaris CS 276061 B6 Substance IC 50 of chlorophyll synthesis MIC chlorophyll synthesis Ι05θ 10 "6 mol.dm-3 growth of rays I 49.0 234.0 91.6 II 26.9 200.0 44 , 6 III 15.1 57.5 21.4 IV 61.7 25.1 83.2 V 25.7 61.7 34.7 VI 22.9 50.0 29.5 VII 11.5 26.3 17 , 8 VIII 9.3 25.1 13.8 IX 26.9 51.3 34.7 X 13.8 25.1 27.5 XI 9.1 25.1 10.0 XII 18.6 28.2 23 , 4 XIII 9.3 14.5 10.0 XIV 8.7 18.2 10.0 XV 10.0 17.4 11.2 IC 50 is the concentration of the study substance at which 50% of the inhibited algal parameter is present MIC denotes the minimum concentration of study substance at which inhibition of the evaluated rlas parameter occurs.
The following example further illustrates the activity of the compounds according to the invention on green algae. Example 1 Effect of Compounds of the Invention on Chlorella vulgaris Growth and Synthesized Chlorophyll Content
Algae Chlorella vulgaris was cultured with a staclonary cult and deflected at a temperature of 25 + 1 ° C, a light regime of 16 hours light -8 hours darkness, in a culture medium according to Seslica / Spoiler I: Annual Report of Algolog.Lab. for 1967, 71-140, Trebon, 1968 /. To the nutrient medium, a solution of the study compound was added in a distilled aqueous concentration to obtain a series of culture flasks and graded with the concentration of the substance and the graded biological effect. The flasks were inoculated with a precise volume of homogeneous suspension of rays. After a 7-day culture, the volume of culture medium was filled with distilled water to a flooding volume / equilibrium of water evaporation and the absorbance at 660 nm / proportional to the amount of cells was measured in the cell suspension and the chlorophyll content after extraction! dimethylformamide from centrifuged rlases. The total content of chlorophyll algae in the culture medium was evaluated by the equation:
Chl / mg.dm “^ / 17.9 Ag4? +8.08 Agg4 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 Physlol. 77/2 /. 483-5, 1985
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS903476A CS276061B6 (en) | 1990-07-13 | 1990-07-13 | Alkoxyphenylcarbamic acid pyrrolidinoethyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS903476A CS276061B6 (en) | 1990-07-13 | 1990-07-13 | Alkoxyphenylcarbamic acid pyrrolidinoethyl esters |
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| Publication Number | Publication Date |
|---|---|
| CS347690A3 CS347690A3 (en) | 1992-01-15 |
| CS276061B6 true CS276061B6 (en) | 1992-03-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS903476A CS276061B6 (en) | 1990-07-13 | 1990-07-13 | Alkoxyphenylcarbamic acid pyrrolidinoethyl esters |
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| CS347690A3 (en) | 1992-01-15 |
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