CS276060B6 - Algicidal composition not based on piperidinoethyl esters of substituted alkoxyphenylcarbamates - Google Patents

Abstract

Algicidal agent, which contains as an active substance a compound of the general formula I where OR means alkoxyl β with 1 to 10 carbon atoms in the ortho-, meta- or para- position of the benzene nucleus. The synthesis of these compounds is the subject of the Czech copyright certificate No. 169379 of the authors: Borovanský A., Čižmárik J., Beneš L., Lukáš A., Švec P. /1977/. The compounds are algicidal at concentrations of 7.9.10”° mol.dm“-’ and higher/i.e. at concentrations of 3.2 mg.dm“-5 and higher/.

Description

The invention relates to an algicidal composition which contains a compound of the formula I as active ingredient

Cl® / 1 / wherein OR represents alkoxy1 β 1 to 10 carbon atoms in the ortho-, meta- or para-position of the benzene nucleus.

The synthesis of compounds of formula I is the subject of Cs. author's certificate No., 168379 authors: Borovanaký A., Čižmárik J., Beneš L., Lukáš A., Švec P. / 1977 /. These compounds show locally anesthetic activity ^{. III. IV. V. VI. VII, VIII. IX. X. XI. XII.} / Čižmárik J „, Borovanský A., Švec P .; Acta Fac. Pharm, Univ.Comeniane XXIX, 53, 1976 /.

In a further study of the biological activity of the compounds of formula I, we found that these significantly inhibited the growth and synthesis of algal chlorophyll.

The inhibitory activity of the compounds of the formula I on rlases was tested by stationary cultivation of a synchronous rlas culture of Chlorella vulgaris. Rise cells as well as the content of synthesized chlorophyll were evaluated. A detailed description of the evaluation method is given in Example 1. The degree of analgesic activity of the compounds of general formula I is expressed by the data in tab. 1. The inhibitory effect on hair was monitored for the following compounds of formula I:

I. N- (2- (2-methoxyphenylcarbamoyloxy) -ethyl] -piperidine hydrochloride

II. N- [3- (3-methoxyphenylcarbamoyloxy) -ethyl] -piperidine hydrochloride

III. N- {2 '(4-methoxyphenylcarbamoyloxy) -ethyl) -piperidine hydrochloride

IV. N- [2 - (2-ethoxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

V. N- [2- (3-ethoxyphenylcarbamoyloxy) -ethyl] -piperidine hydrochloride

VI. N- [2- (4-ethoxyphenylcarbamoyloxy) -ethyl] -piperidine hydrochloride

VII, N- [2- (2-propoxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

VIII. N- (2- (3-propoxyphenylcarbamoyloxy) ethyl) -piperidine hydrochloride

IX. N- [2- (4-propoxyphenylcarbamoyloxy) -ethyl] -piperidine hydrochloride

X. N- [2- (2-butoxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XI. N-E2- (3-butoxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XII. H- [2- (4-butoxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XIV. N- [2- (3-pentyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XV. N- [2- (4-pentyloxyphenylcarbamoyloxy) ethyl] piperidinium chloride

XVI. N- [2- (2-hexyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XVII. N- [2- (3-methoxyloxyphenylcarbamoyloxy) ethyl] -piperidinium chloride

XVIII.N- [2- (4-hexyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XIX. N- [2- (2-heptyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XX. N- [2- (3-heptylozyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XXII. N- [2- (2-octyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XXIII.N- [2- (3-Octyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XXIV. N- [2- (4-octyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XXV. N- [2- (2-nonyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride

XXVI. N-E2- (3-nonyloxyphenylcarbamoyloxy) -ethyl-piperidinium chloride

XXVII. (2- (4-nonyloxyphenylcarbamoyloxy) J-ethyl] -piperidinium chloride XXVIII.N- | 2- (2-decyloxyphenylcarbamoyloxy) -ethyl] -piperidinium chloride XXIX. - {2- (4-decyloxyphenylcarbamoyloxy) -ethyl) -piperidinium chloride

Table 1

Inhibitory activity of the compounds of formula I on Chlorella vulgaris

Fabric 2. ^IC 50 of chlorophyll synthesis MIC chlorophyll synthesis ^IC 50 growth algae 10 “ ⁶ mol.dm“ ^ I 24.5 316.0 107.2 II 30.2 87.1 50.0 III 21.9 57.5 32.3 IV 20.9 100.0 42.7 in 22.9 55.0 35.5 VI 22.9 40.7 33.5 VII 24.0 79.4 33.9 VIII 10.7 39.8 15.1 IX 11.2 20.0 14.1 X 30.9 83.1 28.8 XI 11.5 14.8 13.8 XII 0.9 12.6 9.4 xrv 5.9 11.0 7.9 XV 9.5 13.8 10.7 XVI 9.5 14.1 12.9 XVII 5.8 10.8 8.3 XVIII 5.2 8.1 5.8 XIX 8.3 10.7 8.9 XX 6.9 9.1 9.5 XXII 3.5 13.2 10.2 XXIII 6.8 11.5 10.7 XXIV 1.8 7.9 4.4 XXV 22.9 346.0 22.4 XXVI 19.4 61.7 25.7 XXVII 7.1 11.2 7.8 XXVIII 407.0 1000 1000 XXIX 51.3 126.0 83.2 XXX 33.9 138 38.0

IC ₅₀ indicates the concentration of the test substance at which 50% inhibition of the evaluated algal parameter occurs relative to control samples.

MIC indicates the minimum concentration of the test substance at which tight inhibition of algal parameters occurs.

The following example further illustrates the inhibitory activity of the compounds of the invention on green rays.

Example 1

The effect of the compounds according to the invention on the growth of the algae Chlorella vulgaris and the content of synthesized chlorophyll

Algae Chlorella vulgaris were grown by ationic cultivation at 25 + 1 ° C, in avetal regime 16 hours light - 8 hours dark, in culture medium according to Žetlík / Šetlík I .: Annual Report of Algolog. Lab. for 1967, 71-140, Třeboň, 1968 /. A solution of the study compound in distilled water was added to the nutrient medium in such a concentration as to obtain a series of culture flasks with a graded concentration of substance and a graded biological effect. The flasks were inoculated with the exact volume of a homogeneous algal suspension. After culturing for 7 days, the volume of the culture medium was made up to volume with the original volume (equalization of water evaporation) and in suspension! The absorbance at 660 nm (proportional to the number of algal cells) and the chlorophyll content after its extraction were measured. dimethylformamide from centrifuged algal cells. The total chlorophyll content of algae in the culture medium was evaluated according to the equation: Cbl / mg.dm ^ / 17.9 Ag ^ y + 8.08 Agg ₄ where A is the absorbance of the sample at 647, resp. 664.5 nm in 1 cm swing (Inskeep WPJ Bloom PR: Plant Physiol. 77/2 /, 483-5, 1985 /.

The obtained values of these parameters were compared with the values of the parameters of the control samples (evaluated as% of the control). Based on these values, the concentrations of the studied compounds at which 50% inhibition was achieved (ΙΟ ^ θ) and, in the case of chlorophyll values, also complete inhibition (MIC) were calculated by extrapolation. The MIC was not evaluated from the absorbance values, as this method also determines the discolored dead algal cells, and thus even with complete inhibition, certain absorbance values are measured.

For example, to test the effect of Compound XIX, 0.12 mL of an aqueous solution of Compound XIX of the following concentrations was added to 12 ml of algal inoculum culture medium:

2.0.10 \ l, 0.10 \ 8.0.104, 5.0.10 "^ and 2.0.10" ^ mól.dm ^. The actual concentrations of compound XIX in the culture medium and the corresponding values of inhibition of algal growth and chlorophyll synthesis, expressed in% of control samples, are given in Tab. 2.

Values of the concentration of the studied compound at which 50% of it, resp. complete inhibition of the studied algal parameter is determined by extrapolation from the dependence of the above values of the% inhibition of the observed parameter on the logarithm of the applied concentration of the studied compound.

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CS 276060 B6 »

Table 2.

Inhibition of algal growth and chlorophyll synthesis in the presence of compound XIX

Conc. XIX 10θ mol.dm “· ^ % control + Chlorophyll Absorbance 20 0 17.9 ± 0.9 10 17.6 ± 4.9 35.1 ± 4.6 8 58.7 ± 4.2 66.2 ± 4.5 5 102.2 ± 1.6 108.6 ± 1.2 2 104.0 ± 8.2 108.7 +

- standard deviation

Claims (2)

Tabuťka 2. Inhibition of Algae Growth and Chlorophyll Synthesis in the Presence of Compound XIX CS 276060 B6 Final Chain, XIX 10 "θ mole.dm" · ^% Control + (i Chlorophyll Absorbancla 20 0 17.9 + 0.9 10 17.6 + 4, 9 35.1 + 4.6 8 58.7 + 4.2 66.2 + 4.5 5 102.2 + 1.6 108.6 + 1.2 2 104.0 + 8.2 108.7 + - standard deviation PATENT REQUIREMENTS Algicidal plant, characterized by the fact that it contains the compound of general formula I as an active substance Cr * (1) wherein OR is a C 1 -C 10 alkoxy in the ortho, meta- or para- position of the benzene ring.