CS276185B6 - Algicide based on 1- (2-alkoxycarbaniloyloxy) cyclohexylmethyl / dimethylammonium chloride - Google Patents

Abstract

Algicidal agent, which contains as an active substance a compound of the general formula I, where R is a straight alkyl with 1 to 5 carbon atoms. The synthesis of compounds according to the general formula X is the subject of Czechoslovak author's certificate No. 253447 of the authors: Gregáň F., Ďurinda J., Tůmová I., Borovanský A. (1982). The compounds according to the invention have an algicidal effect at concentrations of 1.0.10- mol.dm-^ and higher (i.e. 3.9 mg.dm and higher). The compounds can be used alone or in a mixture with other substances as an active component of anti-algal preparations.

Description

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

wherein R is direct alkyl of 1 to 5 carbon atoms.

The synthesis of compounds of formula I is the subject of MS. author's certificate No.-253447 authors: Gregáň F., Ďurinda J., Tůmová I., Borovanský A. (1982). The compounds also have a local anesthetic effect (Gregáň F., Ďurinda J., Tůmová I., Borovanský A .: Ceskoslov. Farm. XXXVI, 448, 1987).

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 algae was tested by stationary cultivation of a synchronous algal culture of Chlorella vulgaris. The growth of algal 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 antialgal activity of the compounds of general formula I is expressed by the data in tab. 1.

The inhibitory effect on algae was monitored for the following compounds of formula I:

I. 1- (2-methoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride

II. [1- (2-ethoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride

III. [1- (2-propoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride

IV. [1- (2-butoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride

V. 1- (2-pentyloxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride

TABLE 1

Inhibitory activity of substances of general formula I on algae Chlorella vulgaris

Fabric ^ 50 chlorophyll synthesis MIC of chlorophyll synthesis ^IC 50 growth algae 10 6mol.dm ~ 3 I. 50.7 107.0 74.1 II. 42.6 107.0 61.7 III. 22.0 60.0 35.1 IV. 6.2 10.0 11.4 in. 209.0 661.0 490.0

IC ₅₀ indicates the concentration of 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 complete inhibition of the evaluated ries parameter occurs.

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

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 stationary cultivation at a temperature of 25 + 1 'c, in a light regime of 16 hours light / 8 hours dark, in the culture medium according to Šctlík (Šetlík I .: Annual Report of Algolog Lab. For 1967, 71 to 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 algae suspension. After culturing for 7 days, the volume of the culture medium was supplemented with distilled water to the flood volume (water evaporation compensation), and the absorbance at 660 nm (proportional to the number of algal cells) and chlorophyll content after its extraction with dimethylformamide from centrifuged algal cells were measured. The total chlorophyll content of algae in the culture medium was evaluated according to the equation: Chi /mg.dm ^ / = 17.9 Ag ^ _? + 8.08 Ag _{64 5} , where A is the absorbance of the sample at 647, resp. Swing 664.5 nm in 1 cm (Inskeep WP, Bloom PB: 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 (IC ₅₀ ) was achieved and, in the case of chlorophyll values, also complete inhibition (MIC) were calculated by extrapolation. The MIC was not evaluated from the absorbance values, since this method also determines discolored dead algal cells, and thus even with complete inhibition, certain absorbance values are measured. .

For example, in the case of testing the effect of [1- (2-butoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride (Compound No. IV), 0.12 ml of an aqueous solution of Compound No. 1 was added to 12 ml of algal inoculum culture medium. IV of the following concentrations: 5.10 ^- ^, I.IO ^- ^, 7,5.10 ^-4 , —4 —4 - —3

5.10 and 1.10 mol.dm. Actual concentrations of compound no. IV 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.

TABLE 2

Inhibition of algal growth and chlorophyll synthesis in the presence of Li- (2-butoxycarbaniloyloxy) cyclohexylmethyl] dimethylammonium chloride (Compound No. IV)

Conc. substance no. IV 10 ® mól.dm $ % control + 0 Chlorophyll Absorbance 50 0 15.3 + 0.7 ¹⁰ 0 12.5 + 0.1 7.5 6.0 ± 0.6 37.2 ± 1.9 5.0 67.5 + 7.0 82.4 + 1.9 1.0 82.8 + 0 90.5 + 3.4

Claims (1)

PATENT CLAIMS Algicidal composition, characterized in that it contains a compound of the general formula as active ingredient