CS276184B6 - Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids - Google Patents
Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids Download PDFInfo
- Publication number
- CS276184B6 CS276184B6 CS902338A CS233890A CS276184B6 CS 276184 B6 CS276184 B6 CS 276184B6 CS 902338 A CS902338 A CS 902338A CS 233890 A CS233890 A CS 233890A CS 276184 B6 CS276184 B6 CS 276184B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ethyl
- kak
- alkoxycarbanilic
- acids
- compounds
- Prior art date
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Algicídny prostriedok, ktorý ako účinnú látku obsahuje zlúčeninu obecného vzorca I, kde OR znamená alkoxyl so 4 až 7 atómami uhlíka v orto- alebo meta-polohe benzénového jadra. Syntéza týchto zlúčenín je predmetom čs. autorského osvedčenia č. 211247 autorov: Csollei J., Beneš L., Borovanský A., Švec P. (1985). Zlúčeniny podlá vynálezu_posobia_|lgicídne pri končentráciách 1.10 mól.dm a vyšších (tj. pri koncentráciách 3,9 mg.dm a vyšších).Algicidal agent, which contains as an active substance a compound of the general formula I, where OR means alkoxy with 4 to 7 carbon atoms in the ortho- or meta-position of the benzene ring. The synthesis of these compounds is the subject of Czechoslovak author's certificate No. 211247 of the authors: Csollei J., Beneš L., Borovanský A., Švec P. (1985). The compounds according to the invention act_algicidally at concentrations of 1.10 mol.dm and higher (i.e. at concentrations of 3.9 mg.dm and higher).
Description
'-x CS 276184 B6
Vynález sa týká algicídneho prostriedku, ktorý ako účinnú látku obsahuje zlúčeninuobecného vzorca I
kde OR znamená alkoxyl so 4 až 7 atómami uhlíka v orto- alebo meta- polohe benzénovéhojadra.
Syntéza zlúčenín obecného vzorca I je predmetom čs. autorského osvedčenia č. 211247autorov: Csóllei J., Beneš L., Borovanský A., Švec P. (1985). Tieto zlůčeniny vykazujú lo-kálně anestetickú účinnost (Csollei J.: Farm. obzor 50, 407, 1981).
Pri dalšom štúdiu biologickej účinnosti zlúčenín obecného vzorca I sme zistili, žetieto výrazné inhibujú rast a syntézu chlorofylu rias.
Inhibičná účinnost zlúčenín obecného vzorca I na riasy sa testovala stacionárnou kul-tiváciou synchronněj kultúry rias Chlorella vulgaris. Hodnotil sa nárast buniek rias, akoaj obsah syntetizovaného chlorofylu. Podrobný popis metody hodnotenia je uvedený v příkla-de 1. Miera antialgálnej účinnosti zlúčenín obecného vzorca I je vyjádřená údajmi v tab. 1.Inhibičný vplyv na riasy sa sledoval u nasledujúcich zlúčenín obecného vzorca I: 1. N-etyl-2-pyrolidinylmetylester 2-butoxykarbanilovej kyseliny, hydrochlorid (pracovnéoznačenie KAK 2224) 2. N-ety1-2-pyrolidinylmetylester 2-pentyloxykarbanilovej kyseliny, hydrochlorid (KAK 2225) 3. N-etyl-2-pyrolidinylmetylester 2-hexyloxykarbanilovej kyseliny, hydrochlorid (KAK 2226) 4. N-etyl-2-pyrolidinylmetylester 2-heptyloxykarbanilovej kyseliny, hydrochlorid (KAK 2227) 5. N-etyl-2-pyrolidinylmetylester 3-butoxykarbanilovej kyseliny, hydrochlorid (KAK 2234) 6. N-etyl-2-pyrolidinylmetylester 3-pentyloxykarbanilovej kyseliny, hydrochlorid (KAK 2235) 7. N-etyl-2-pyrolidinylmetylester 3-hexyloxykarbanilovej kyseliny, hydrochlorid (KAK 2236) 8. N-cty1-2-pyrolidinylmctylcstcr 3-hcptyloxykarbanilovcj kyseliny (KAK 2237). TABULKA 1
Inhibičná účinnost látok obecného vzorca I na riasy Chlorella vulgaris Látka IC50 MIC IC50 10-6mól.dm“3 syntézy syntézy rastu chlorofylu chlorofylu rias KAK 2224 39,4 66,1 53,7 KAK 2225 23,4 60,3 30,2 KAK 2226 14,5 50,1 20,9 KAK 2227 8,0 15,8 12,0 KAK 2234 13,2 39,8 20,9 KAK 2235 12,3 25,1 15,0 KAK 2236 6,8 10,0 8,7 KAK 2237 6,9 11,0 8,3 CS 276184 B6 IC,-0 značí koncentráciu študovanej látky, pri ktorej dochádza k 50 %nej inhibícii hodnotc-ncho parametra rias vzhladom na kontrolné vzorky; MIC značí miniraálnu koncentráciu študovanej látky, pri ktorej dochádza k úplncj inhibíciihodnotenóho parametra rias.
Nasledujúci příklad bližšie osvětluje inhibičnú účinnost zlúčenín podlá vynálezu nazelené riasy. Příklad 1 Účinok zlúčenín podlá vynálezu na rast rias Chlorella vulgaris a obsahsyntetizovaného chlorofylu
Riasy Chlorella vulgaris sa pěstovali stacionárnou kultiváciou pri teplote 25+1 'c, pri svetelnom režime 16 hodin světlo - 8 hodin tma, v kultivačnom médiu podlá Setlíka (Setlík I.: Annual Report of Algolog Lab. for 1967, 71-140, Třeboň, 1968). K živnému médiu sa přidával roztok študovanej zlúčeniny v destilovanéj vodě takej koncentrácie, aby sa získala séria kultivačných baniek s bdstupňovanou koncentráciou látky a odstupňovaným bio-·· * logickým účinkom. Banky sa inokulovali přesným objemom homogénnej suspenzie rias. Po7-dennej kultivácii sa objem kultivačného média doplnil destilovanou vodou na povodný ob-jem (vyrovnanie odparu vody) a v suspenzii buniek sa merala absorbencia pri 660 nm (úměr-ná množstvu buniek rias) a obsah chlorofylu po jeho extrakcii dimetylformamidom z odcen-trifugovaných buniek rias. Celkový obsah chlorofylu rias v kultivačnom médiu sa vyhodno-til podlá rovnice: Chl /mg.dm 3/ = 17,9 Ag^? + 8,08 Agg^ g, kde A je absorbancia vzorkypri 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 kontrolnýchvzoriek (vyhodnotené ako % kontroly). Na základe týchto hodnot sa extrapoláciou vyčíslilikoncentrácie študovaných zlúčenín, pri ktorých sa dosiahla 50 %ná inhibícia (ICgg) a vpřípade hodnot chlorofylu aj úplná inhibícia (MIC). Z hodnot absorbancie sa MIC nevyhodno-covala, nakolko touto metodou sa stanovujú tiež odfarbené mřtve buňky rias, a teda aj priúplnéj inhibícii sa namerajú určité hodnoty absorbancie.
Například v případe testovania účinku zlúčeniny KAK 2237 sa k 12 ml kultivačného mé-dia s inokulom rias přidalo 0,12 ml vodného roztoku zlúčeniny KAK 2237 nasledovných kon-centrácií: 2,5.10-3, 1.10-3, 7,5.1θ"4, 5.10-4 a 1.10-4 mól.dra~3. Skutočné koncentráciezlúčeniny KAK 2237 v kultivačnom médiu a příslušné hodnoty inhibície rastu rias a synté-’zy chlorofylu, vyjádřené v % kontrolných vzoriek sú uvedené v tab. 2.
Hodnoty koncentrácie študovanej zlúčeniny, pri ktorej dochádza k 50 %nej, resp. úpl-nej inhibícii študovaného parametra rias sa zistuje extrapoláciou zo závislosti vyššieuvedených hodnot % zistenej inhibície sledovaného parametra od logaritmu aplikovanej kon-centrácie študovanej zlúčeniny. TABULKA 2
Inhibícia rastu rias a syntézy chlorofylu v přítomnosti zlúčeniny KAK 2237 G"' = smerodajná odchýlka
Konc. zlúč. KAK 2237 % kontroly + ”*6 ""3 10 mól.dm Chlorofyl Absorbancia 25 0 12,5 + 0 10 9,3 + 0,7 18,5 + 2,0 7,5 47,5 + 7,7 63,3 + 1,1 5,0 85,4 + 3,6 86,0 + 3,0 1,0 110,6 + 3,0 106,2 + 4,4
CS-276184 B6
The present invention relates to an algicidal composition which comprises a compound of formula I as active ingredient
wherein OR is 4 to 7 carbon atoms in the ortho or meta position of the benzene ring.
The synthesis of compounds of formula I is the subject of MS. Certificate No. 211247Author: Csóllei J., Beneš L., Borovanský A., Švec P. (1985). These compounds exhibit locally anesthetic activity (Csollei J .: Farming Horizon 50, 407, 1981).
In a further study of the biological activity of the compounds of formula I, we have found that these significantly inhibit the growth and synthesis of algal chlorophyll.
The algae inhibitory activity of the compounds of formula I was tested by stationary culture of synchronous algal culture Chlorella vulgaris. An increase in algal cells was evaluated, such as the content of chlorophyll synthesized. A detailed description of the evaluation method is given in Example 1. The level of anti-oral efficacy of the compounds of Formula I is shown in Table 1 below. 1. The algae inhibitory effect was observed for the following compounds of the formula I: 1. N-ethyl-2-pyrrolidinylmethyl ester of 2-butoxycarbanilic acid hydrochloride (KAK 2224 working label) 2. N-ethyl-2-pyrrolidinylmethyl ester of 2-pentyloxycarbanilic acid hydrochloride (KAK 2225) 3. N-Ethyl-2-pyrrolidinylmethyl ester of 2-hexyloxycarbanilic acid hydrochloride (KAK 2226) 4. N-Ethyl-2-pyrrolidinylmethyl ester of 2-heptyloxycarbanilic acid hydrochloride (KAK 2227) 5. N-ethyl-2- 3-butoxycarbanilic acid pyrrolidinylmethyl ester hydrochloride (KAK 2234) 6. 3-pentyloxycarbanilic acid N-ethyl-2-pyrrolidinylmethyl ester hydrochloride (KAK 2235) 7. N-ethyl-2-pyrrolidinylmethyl ester of 3-hexyloxycarbanilic acid hydrochloride (KAK 2236) N-ethyl-2-pyrrolidinylmethylcyclohexylcarbonic acid (KAK 2237). TABLE 1
Inhibitory activity of compounds of formula I on Chlorella vulgaris algae Substance IC50 MIC IC50 10-6 mole.dm 3 chlorophyll chlorophyll synthesis synthesis algae KAK 2224 39,4 66,1 53,7 KAK 2225 23,4 60,3 30,2 KAK 2226 14,5 50,1 20,9 KAK 2227 8,0 15,8 12,0 KAK 2234 13,2 39,8 20,9 KAK 2235 12,3 25,1 15,0 KAK 2236 6,8 10 IC, -0 indicates the concentration of the study substance at which 50% inhibition of the algal parameter is observed with respect to the control samples; MIC denotes the miniraal concentration of the study substance at which complete inhibition of the measured algal parameter occurs.
The following example further 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 were grown by stationary cultivation at 25 + 1 ° C, under light regime 16 hours light - 8 hours dark, in culture medium by Setlík (Setlík I .: Annual Report of Algolog Lab. For 1967, 71-140, Třeboň , 1968). To the nutrient medium, a solution of the study compound in distilled water was added to a concentration to obtain a series of culture flasks with a graded concentration of substance and a graded bio-logical effect. The flasks were inoculated with an exact volume of homogeneous algae suspension. After 7 days of culture, the volume of the culture medium was supplemented with distilled water to the flood volume (water vapor equalization) and the absorbance at 660 nm (proportional to the amount of algal cells) and the chlorophyll content after extraction with dimethylformamide from the effluent were measured in the cell suspension. cell algae. The total algal chlorophyll content in the culture medium was evaluated according to the equation: Chl / mg.dm 3 / = 17.9 Ag =? + 8.08 Agg / g, where A is the absorbance of the sample at 647, respectively. 664.5 nm in 1 cm nod (Inskeep WP, Bloom PR: Plant Physiol. 77 (2), 483-5, 1985). The obtained values of these parameters were compared with the values of the control sample parameters (evaluated as% of control). Based on these values, extrapolation was used to quantify the concentration of the compounds studied in which 50% inhibition (ICgg) and complete inhibition (MIC) were achieved. From the absorbance values, the MIC was not evaluated because this method also determined bleached algal cell counts, and thus, some absorbance values were also measured by total inhibition.
For example, when testing the effect of compound KAK 2237, 0.12 ml of an aqueous solution of KAK 2237 of the following concentrations was added to 12 ml of algal inoculum culture medium: 2.5.10-3, 1.10-3, 7.5.1θ "4 The actual concentrations of the compound KAK 2237 in the culture medium and the respective algal growth inhibition and chlorophyll synthesis values, expressed as a percentage of the control samples, are shown in Table 2.
The concentration of the study compound at which 50% of the compound is studied, respectively. the complete inhibition of the algal parameter studied is determined by extrapolation from the dependence of the aforementioned% found inhibition of the observed parameter on the logarithm of the applied compound concentration. TABLE 2
Inhibition of algal growth and chlorophyll synthesis in the presence of KAK 2237 G "" = standard deviation
Conc. bile. KAK 2237% control + ”* 6""3 10 mol.dm Chlorophyll Absorbance 25 0 12.5 + 0 10 9.3 + 0.7 18.5 + 2.0 7.5 47.5 + 7.7 63 , 3 + 1.1 5.0 85.4 + 3.6 86.0 + 3.0 1.0 110.6 + 3.0 106.2 + 4.4
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS902338A CS276184B6 (en) | 1990-05-14 | 1990-05-14 | Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS902338A CS276184B6 (en) | 1990-05-14 | 1990-05-14 | Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS233890A3 CS233890A3 (en) | 1992-04-15 |
| CS276184B6 true CS276184B6 (en) | 1992-04-15 |
Family
ID=5360211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS902338A CS276184B6 (en) | 1990-05-14 | 1990-05-14 | Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS276184B6 (en) |
-
1990
- 1990-05-14 CS CS902338A patent/CS276184B6/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS233890A3 (en) | 1992-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Küpper et al. | Environmental relevance of heavy metal-substituted chlorophylls using the example of water plants | |
| EP3061750A1 (en) | Pyrazole amide compound containing diphenyl ether, and application thereof, and pesticide composition | |
| CN103060256B (en) | Culturing method capable of promoting grease accumulation in chlorella | |
| Dorn et al. | [Ag (isonicotinamide) 2NO3] 2–a stable form of silver nitrate | |
| MX392286B (en) | Fungicidal composition and method for controlling plant diseases | |
| Liu et al. | Toxic effects of 1-methyl-3-octylimidazolium bromide on the wheat seedlings | |
| CN102106346A (en) | Water hyacinth inhibitor, preparation method and method for inhibiting water hyacinth by inhibitor | |
| CN119632039B (en) | Application of an organic trisulfide compound in promoting plant growth and a plant growth promoter | |
| CS276184B6 (en) | Algicidal composition of the N-ethyl-2-pyrrolidinylmethyl ester type of alkoxycarbanilic acids | |
| CN112237187B (en) | Application of phenolic compound as nematicide | |
| CS276178B6 (en) | Algicidal composition of the type N-alkyl-4-piperidyl esters of alkoxycarbanilic acids | |
| CS276186B6 (en) | Algicidal composition based on 1- (2- / alkoxycarbaniloyloxycycloheptyl) / methyl / piperidinium chloride | |
| CS276185B6 (en) | Algicide based on 1- (2-alkoxycarbaniloyloxy) cyclohexylmethyl / dimethylammonium chloride | |
| CS276062B6 (en) | Alkoxyphenylcarbamic acid dimethylaminoethyl ether aliphatic agent | |
| SK206092A3 (en) | Algicidal agent of n-£2-(2-heptyloxyphenylcarbamoyloxy)- ethyl|-n-alkylpiperidiniumbromides type | |
| CS276061B6 (en) | Alkoxyphenylcarbamic acid pyrrolidinoethyl esters | |
| SK277958B6 (en) | Algicidal aget | |
| SK205592A3 (en) | Algicide agent of morpholineethylesters of substituted alcoxyphenylecarbame acids type | |
| CN115791716B (en) | A method for detecting the biological toxicity of chlorella pyrenoidosa by fluorescence | |
| LU500238B1 (en) | Efficient inhibitor of microcystis aeruginosa and preparation method and application thereof | |
| SK278130B6 (en) | 1-methyl-2-(2-diethylaminoetoxy)-ethylesters of alkoxyphenylcarbames acids | |
| US8945397B2 (en) | Methods of inhibiting cyanobacteria growth by administering gramine derivatives | |
| SK278266B6 (en) | 1-methyl-2-(n-piperidinyletoxy)ethylesters alcoxyphenylalcarbame acids and method of their production | |
| Jiang et al. | Uptake of nitrogen and production of kainic acid by laboratory culture of the red alga Digenea simplex | |
| CS275634B6 (en) | A regulating effect on algal growth and chlorophyll synthesis |