Cite this article as:

Rogachaeva S. M., Zhutov A. S., Shilova N. A., Klochkova I. ., Borisova S. V. Assessment of Growth-Regulating Activity and Ecotoxicity of Diarylidene-Substituted Cyclohexanones. Izvestiya of Saratov University. New series. Series: Chemistry. Biology. Ecology, 2020, vol. 20, iss. 2, pp. 137-145. DOI: https://doi.org/10.18500/1816-9775-2020-20-2-137-145


Heading: 
UDC: 
57.084.1:574.64
Language: 
Russian

Assessment of Growth-Regulating Activity and Ecotoxicity of Diarylidene-Substituted Cyclohexanones

Abstract

The search of new biologically active substances to be used as herbicides and plant growth regulators is carried out. The two compounds were used – 2-benzylidene-6-(m-nitrobenzylidene) cyclohexanone (1) and 2-benzylidene-6-(p-fluorobenzylidene) cyclohexanone (2). They are similar in structure, but containing different functional groups in one of the benzene rings: -NO2, and -F. Their dose-dependent effect on the germination and growth of Triticum aestivum and Barbarea vulgaris was investigated. High concentrations of the both substances completely suppressed seed germination (1 g/L) and inhibited the growth of seedlings of the plants (0.1 g/L). It was found that the compounds showed a growth-regulating effect on selected plant species in the concentration range of 0.0001–0.01 g/L. The compound 1 (0.001 g/L) significantly stimulated seed germination (15%) and seedlings growth of T. aestivum (70–100%), but the influence on the growth of B. vulgaris was lesser. Fluorine-containing compound 2 in the same concentration inhibited the stems growth of T. aestivum seedlings and suppressed the growth of B. vulgaris roots in the first days of experience. Ecotoxicological studies showed that a fluorine-containing compound is more toxic than a compound with a nitrogroup. According to the results of two biotests (S. quadricauda, D. magna), substance 2 at the concentration of 0.01 g/L showed acute toxicity. Both compounds in concentrations less than 0.001 g/L are non-toxic, i.e. they are environmentally safe and can be used as plant growth regulators.

References

1. Gubina T. I., Ukhova A. A., Isaeva S. V., Tumskiy R. S., Aniskov A. A., Klochkova I. N. The Determination of Biological Effects of New Heterocyclic Compounds on Plants and the Evaluation of Environmental Safety of Their Application. Izv. Saratov Univ. (N. S.), Ser. Chemistry. Biology. Ecology, 2017, vol. 17, iss. 3, pp. 267–273 (in Russian). DOI: https://doi.org/10.18500/1816-9775-2017-17-3-267-273
2. Korobko V. V., Pchelintseva N. V., Lunyova М. А., Samsonovа E. A. Features of Growth and Development of Wheat Seedlings (Triticum aestivum L.) under the Action of 2,4,6-Triphenyl-3,5-dichloropyridine and 2,6-Diphenyl-3-chloropyridine. Izv. Saratov Univ. (N. S.), Ser. Chemistry. Biology. Ecology, 2017, vol. 17, iss. 1, pp. 72–78 (in Russian). DOI: https://doi.org/10.18500/1816-9775-2017-17-1-72-78
3. Mironova N. V., Korobko V. V., Pchelintseva N., Krylatova Ya. G., Zhestovskaya E. S. The Phytotesting of (thio)semicarbazones 2,4-diarylbicyclo[3.3.1]non-2-en9-ones. Izv. Saratov Univ. (N. S.), Ser. Chemistry. Biology. Ecology, 2019, vol. 19, iss. 3, pp. 305–311 (in Russian). DOI: https://doi.org/10.18500/1816-9775-2019-19-3-305-311
4. Timofeeva Z. Yu., Chadina V. V., Yegorova A. Yu. Growth-stimulating Activity of Some Arylidene Derivatives of Pyridazine-3-ones and 3h-pyrrol-2-ones. Advances in Current Natural Sciences, 2006, iss. 4, pp. 13–15 (in Russian).
5. Report of the OECD Pesticide Aquatic Risk Indicators Expert Group. 2000. 58 p. [Электронный ресурс]. URL: http://www.oecd.org (дата обращения: 15.09.19).
6. Sipulinov R. B., Karagaycheva Yu. V., Shilova N. A., Rogacheva S. M. Estimation the Toxicity of Oil Production Waste by Biotesting Methods. Izv. of Samara Scientifi c Center of the Russian Academy of Sciences, 2015, vol. 17, no. 5, iss. 2, pp. 695–699 (in Russian).
7. Matorin D. N., Bratkovskaya L. B., Yakovleva O. V., Venediktov P. S. Biotesting of Toxicness of Waters on Speed of Absorption of Microalgae Daphnia Registered by Fluorescence of Chlorophyll. Moscow University Biological Sciences Bulletin, 2009, iss. 3, pp. 28–33 (in Russian).
8. Biochemistry of Plant Secondary Metabolism / ed. M. Wink. Oxford: Wiley-Blackwell, 2010. Vol. 40. 445 p. DOI: https://doi.org/10.1002/9781444320503.
9. Federal’nyi reestr (FR) FR.1.39.2007.03223. Metodika opredeleniya toksichnosti vod, vodnykh vytyazhek iz pochv, osadkov stochnykh vod i otkhodov po izmeneniyu urovnya fl uorestsentsii khlorofi lla i chislennosti kletok vodorosley [Federal register (FR) FR.1.39.2007.03223. Method for determining the toxicity of water, water extracts from soil, sewage sludge and waste by changing the level of chlorophyll fl uorescence and the number of algae cells]. Moscow, AKVAROS Publ., 2007, 53 p. (in Russian).
10.  Federal’nyi reestr (FR) FR.1.39.2007.03222. Metodika opredeleniya toksichnosti vody i vodnykh vytyazhek iz pochv, osadkov stochnykh vod, otkhodov po smertnosti i izmeneniyu plodovitosti dafniy [Federal register (FR) FR.1.39.2007.03222. Methods for determining the toxicity of water and water extracts from soils, sewage sludge, waste by mortality and changes in the fertility of daphnia]. Moscow, AKVAROS, 2007. 52 p. (in Russian).

Short text (in English): 
Full text (in Russian):