CS276178B6 - Algicidal composition of the type N-alkyl-4-piperidyl esters of alkoxycarbanilic acids - 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 2 to 4 carbon atoms and OR„ is an alkoxyl with 4 to 7 carbon atoms in the ortho- or meta-position of the benzene ring. The synthesis of these newly synthesized compounds is given in the work of the authors CsOllei J., Beneš L., Borovanský A., Švec P., Béderová E., Kozlovský J.: Českoslov. farm. XXXV. 229 (1986). The compounds are algicidal at concentrations of 6.10" mol.dm"J and higher (i.e. at concentrations of 2.3 mg.dm"-5 (and higher).

Description

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

CD, wherein R ₁ is straight alkyl of 2 to 4 carbon atoms and OR 8 is alkoxyl of 4 to 7 atoms in the ortho or meta-position of the benzene ring.

The synthesis of newly synthesized hitherto undescribed compounds of general formula I is described in the work of Csdllei J., Beneš L., Borovanský A., Švec P., Béderová E., Kozlovsky J .: Českoslov. farm. XXXV, 299 (1986). The compounds show local anesthetic activity.

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 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 formula I is expressed by the data in Table 1. The inhibitory effect on algae was monitored for the following compounds of formula I:

1. 2-Butoxycarbanilic acid N-ethyl-N-piperidyl ester, hydrochloride (trade designation 4224) ·

2. 2-Pentyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4225)

3. 2-Hexyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4226)

4. 2-Heptyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4227)

5. 3-Butoxycarbanilic acid N-ethyl-4-piperidyl ester, hydrochloride (PAK 4234)

6. 3-Pentyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4235)

7 · 3-Hexyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4236)

8. 3-Heptyloxycarbanilic acid N-ethyl-4-piperidyl ester hydrochloride (PAK 4237)

9. 2-Butoxycarbanilic acid N-propyl-4-piperidyl ester, hydrochloride (PAK 4324)

10. 2-Pentyloxycarbanilic acid N-propyl-4-piperidyl ester, hydrochloride (PAK 4325)

11. 2-Hexyloxycarbanilic acid N-propyl-4-piperidyl ester hydrochloride (PAK 4326)

12. 2-Heptyloxycarbanilic acid N-propyl-4-piperidyl ester hydrochloride (PAK 4327)

13. 3-Butoxycarbanilic acid N-propyl-4-piperidyl ester, hydrochloride (PAK 4334) 14 · 3-Pentyloxycarbanilic acid N-propyl-4-piperidyl ester, hydrochloride (PAK 4335) 15. 3-Hexyloxycarbanilic acid N-propyl-4-piperidyl ester acids, hydrochloride (PAK 4336) 16. 3-heptyloxycarbanilic acid N-propyl-4-piperidyl ester, hydrochloride (PAK 4337) 17. 2-butoxycarbanilic acid N-butyl-4-piperidyl ester, hydrochloride (PAK 4424) 18. N-butyl 2-Pentyloxycarbanilic acid -4-piperidyl ester, hydrochloride (PAK 4425) 19. 2-Hexyloxycarbanilic acid N-butyl-4-piperidyl ester, hydrochloride (PAK 4426) 20. 2-Heptyloxycarbanilic acid N-butyl-4-piperidyl ester, hydrochloride (PAK 4427) 21. 3-Butoxycarbanilic acid N-butyl-4-piperidyl ester, hydrochloride (PAK 4434) 22. 3-Hexyloxycarbanilic acid N-butyl-4-piperidyl ester, hydrochloride (PAK 4436) 23. N-butyl-4-piperidyl ester 3 -heptyloxycarbanilic acid hydrochloride (PAK 4437) Table 1

Inhibitory activity of the compounds of formula I on algae Chlorella vulgaris

CS 276 ’78 B6

Fabric ^IC 50 of chlorophyll synthesis MIC ' chlorophyll synthesis IC _Kn 10 ' ⁶ mól.dm “ ³ 50 rastu algae PAK 4224 50.0 20.4 27.5 ' PAK 4225 50.0 30.2 34.7 . PAK 4226 33.1 10.7 13.8 PAK 4227 10.2 8.7 8.9 PAK 4234 11, 0 8.7 8.7 PAK 4235 9.1 7.9 7.9 PAK 4236 6.0 3.8 4.6 ’PAK 4237 11.5 7.4 8.4 . PAK 4324 60.3 17.4 28.8 . PAK 4325 25.1 1 1, 8 15.1 PAK 4326 25.1 11.8. 11.5 PAK 4327 25.1 13.5 2 2.9 PAK 4334 16.2 5.4 7.4 PAK 4335 10.0 5.5 6.1 PAK 4336 8.7 4.2 4.6 PAK 4337 10.0 5.8 7.6 PAK 4424 19.9 8.3 12.6 PAK 4425 20.0 10.5 10.5 PAK 4426 39.8 12.0 20.9 PAK 4427 35.5 13.8 16.6 PAK 4434 15.8 9.6 9.1. PAK 4436 10.0 7.1 8.3 PAK 4437 15.1 9.8 ¹ 1.5 ICcq indicates the concentration of the test substance at which 50% occurs inhibition evaluated algae parameters with respect to control samples; MIC indicates the minimum concentration of the study substance, in which it occurs to complete inhibition of the evaluated algae parameter.

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

Chlorella vulgaris algae were grown by stationary cultivation at 25-1 ° C, in a light regime of 16 hours light / 8 hours dark, in the culture medium according to Šetlík (Šetlík I .: Annual Report of Algolog Lab. For 1967, 71-140, Třeboň , 1968). A solution of the study compound in distilled water of such concentration was added to the nutrient medium 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 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: Chl (mg.dm “ ³ ) = 17.9 + 8.08 Agg ^ 5, where A is the absorbance of the sample at 647, resp. Rocking 664.5 nm in 1 cm (Inskeep WP, 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 study 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 is not evaluated from the absorbance values

CS 276 178 B6 1a, since this method also determines discolored dead algal cells and thus, even with complete inhibition, certain absorbance values are measured.

For example, to test the effect of PAK 4324, 0.12 ml of an aqueous solution of PAK 4324 at the following concentrations of 6.0.10 "^, 3.5.10" ^, 2.5.1θ · \ 1.0.10 was added to 12 ml of algal inoculum culture medium. * 3 a 7> 5.10 * ^ mól.dm ^- ^. The actual concentrations of PAK 4324 in the culture medium and the corresponding values for inhibition of algal growth and chlorophyll synthesis, expressed as% of controls, are shown in Table 2.

The 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 study compound.

Table 2

Inhibition of algal growth and chlorophyll synthesis in the presence of PAK 4324

Conc. compound PAK 4324 1mol.dnT ^ % control + oh Chlorophyll Absorbance 60 0 18.7 2 ° » ² 35 25.6 ± 6.5 45.7 2 ¹ > 3 25 38.1 ± 3.7 58.0 ± 2.0 10 68.9 2 ¹⁰ ? ⁸ 87.5 2 2.8 7.5 82.8 ± 3.0 94.8 2 ^{1 .9}

6- standard deviation

Claims (1)

PATENT CLAIMS Algicidal composition, characterized in that it contains a compound of the formula I as active ingredient ^R 1 (I), wherein R ₁ is straight alkyl of 2 to 4 carbon atoms and OR ₂ is alkoxyl of 4 to 7 carbon atoms in the ortho- or meta-position of the benzene ring.