Plant Soil Environ., 2005, 51(11):496-505 | DOI: 10.17221/3623-PSE

Benzothiazole derivatives substituted in position 2 as biologically active substances with plant growth regulation activity

E. Šimonová, M. Henselová, P. Zahradník
Faculty of Natural Sciences, Comenius University in Bratislava, Slovakia

Thirteen of the new synthetized 2-R substituted benzothiazole derivatives have been tested for plant growth regulatory (PGR) activity. The effect on growth elongation was studied on wheat coleoptile segments Triticum aestivum L. cv. Blava, and on the hypocotyl and roots in cucumber Cucumis sativum L. cv. Evita. The formation and number of adventitious roots and the length of hypocotyl in Vigna radiata (L.) Wilczek and, the effect on the length of stem, fresh and dry mass in buckwheat Fagopyrum esculentum Moench. cv. Pyra were evaluated. Cytokinin activity was determined on segments of barley leaves Hordeum vulgare L. cv. Jubilant on the basis of senescence inhibition and chlorophyll content. The benzothiazole derivatives were tested in the range of 10-3-10-7M concentrations, and PGR activity was compared with indole-3-acetic acid, indole-3-butyric acid and 6-furfurylaminopurine. All tested derivatives showed different auxine-like effects on elongation growth of plants and the stimulative effects were found to depend on applicable concentrations. At higher concentration rates, derivatives acted as growth retardants and inhibited the length of cucumber hypocotyl and roots. The derivatives increased the formation of adventitious roots of mung bean hypocotyl cuttings, as well as stem elongation and production of fresh and dry mass of buckwheat. Cytokinin activity was confirmed in one derivate only with a significant effect on the inhibition of leaf senescence and higher chlorophyll content. The tested benzothiazole derivatives may be characterized as biologically active substances with dominant auxine-like growth promoting activity

Keywords: benzothiazole derivatives; elongation growth; root formation, senescence; Cucumis sativum; Fagopyrum esculentum; Hordeum vulgare; Triticum aestivum; Vigna radiata

Published: November 30, 2005  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Šimonová E, Henselová M, Zahradník P. Benzothiazole derivatives substituted in position 2 as biologically active substances with plant growth regulation activity. Plant Soil Environ. 2005;51(11):496-505. doi: 10.17221/3623-PSE.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Afsah S.A., Nayer S.A. (1996): Synthesis of some styryl chain substituted benzothiazolium asymmetric cyanines: spectra and antimicrobial studies. Asian Journal of Chemistry, 8: 419-424.
    2. Beckett R.P., Van Staden J. (1992): The effect of thidiazuron on the yield of wheat grown with varying nutrient supply. Plant Growth Regulation, 11: 343-348. Go to original source...
    3. Buffa R., Zahradník P., Foltínová P. (2001): Computer aided benzothiazole derivatives. Synthesis, structure and biological study of new push-pull conjugated benzothiazolium salts. Heterocyclic Communications, 7: 331-336. Go to original source...
    4. Caldiz D.O., Beltrano J., Fernandez L.V., Sarandon S.J., Favoretti C. (1991): Effects of foliar applied benzyladenine on grain yield and grain protein in wheat (Triticum aestivum L.). Plant Growth Regulation, 10: 197-204. Go to original source...
    5. Cavender P.L., Green C.M., Mack S.B. (1988): Antisenescence activity of 4,5-disubstituted imidazoles: new cytokinin mimics. Journal of Agricultural and Food Chemistry, 36: 1076-1079. Go to original source...
    6. Chang I.K., Foy C.L. (1983): Rapid growth responses of dwarf corn coleoptile sections to picloram. Pesticide Biochemistry and Physiology, 19: 203-209. Go to original source...
    7. Chernyad'ev I.I. (1994): Effect of 6-benzylaminopurine and thidiazuron on photosynthesis in crop plants. Photosynthetica, 30: 287-292.
    8. Cuadro A., Perez-Butragueno J., Pastor-Maeso M., Alvarez-Builla J. (1992): Styryl and azastyryl 1,3-benzazoles with antihelmintic activity. Farmaco, 47:477-488. Go to PubMed...
    9. Davis T.D. (1986): Influence of triazole growth retardants on adventitious root formation in bean hypocotyl cuttings. In: Proceedings of Plant Growth Regulation of Society America, 13: 217-223.
    10. Evans M.L., Schmitt M.R. (1975): The nature of spontaneous changes in growth rate in isolated coleoptile segments. Plant Physiology, 55: 757-762. Go to original source... Go to PubMed...
    11. Foltínová P., Sutoris V., Blockinger G. (1978): Antimicrobial effects of some benzothiazole derivatives. Folia Microbiologica, 23: 225-228. Go to original source... Go to PubMed...
    12. Gaspar T., Hofinger M. (1988): Auxin metabolism during adventitious rooting. In: Davis T.D., Haissig B.E., Sankhla N. (eds.): Adventitious root formation in cuttings. Portland, Dioscorides Press: 117-131.
    13. Grandolini G., Ambrogi V., Rossi C. (1986): Synthesis and antibacterial and antifungal activities of some new derivatives of benzothiazole, 1,4-benzothiazine and 1,5-benzothiazepine. Journal of Medical Chemistry, 21: 455-460. Go to original source...
    14. Halevy A.H., Cathey H.M. (1960): Effects of structure and concentration of gibberellins on the growth of cucumber seedlings. Botanical Gazette, 122: 63-67. Go to original source...
    15. Havel L., Konečná H., Snášelová V., Procházka S., Blažková J. (1994): Vliv benzolinonu a auxinu na regeneraci a aktivitu peroxidáz v explantátové kultuře zelí. Rostlinná Výroba, 40: 783-791.
    16. Henselová M., Vizárová G., Macháčková I. (2001): The effect of growth regulator Rastim 30 DKV on the level of endogenous phytohormones in tomato (Solanum lycopersicum L.). Rostlinná Výroba, 47: 411-417.
    17. Kashiyama E., Hutchinson I., Chua M.S. (1999): Antitumor benzothiazoles. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)-benzothiazoles. Journal of Medical Chemistry, 42: 4172-4184. Go to original source... Go to PubMed...
    18. Kingham H.G., Fletcher J.T. (1963): The effects of MCPA and 2,3,6-TBA on glasshouse cucumbers. Weed Research, 3: 242-245. Go to original source...
    19. Klíčová Š., Šebánek J., Vítková H. (1994): Comparison of the effect of β-indolyl acetic acid and benzolinon (Rastim 30 DKV) on the rate of senescence of oat (Avena sativa L.) leaves. Biologia (Bratislava), 49: 119-123.
    20. Kollárová K., Henselová M., Lišková D. (2005): Effect of auxins and plant oligosacharides on the root formation and elongation growth of mung bean hypocotyls. Plant Growth Regulation, (submitted). Go to original source...
    21. Krieg M., Billitz J. (1996): Structurally modified trimethine thiacarbocyanine dyes. Effect of N-alkyl substituents on antineoplastic behavior. Molecular and Biochemical Pharmacology, 51: 1461-1467. Go to original source... Go to PubMed...
    22. Lee T.T. (1972): Changes in indole acetic acid oxidase isoenzymes in tobacco tissues after treatment with 2,4-dichlorophenoxyacetic acid. Plant Physiology, 49: 957-960. Go to original source... Go to PubMed...
    23. Magdolen P. (1999): Benzotiazolové soli s biologickou aktivitou. [PhD. Thesis.] Faculty of Natural Sciences, Comenius University, Bratislava.
    24. Magdolen P., Zahradník P., Foltínová P. (2000a): Synthesis and antimicrobial activity of new 2-phenylethynylbenzothiazoles and related salts. Arzneimittel-Forschung/ Drug Research, 50: 1023-1027. Go to original source... Go to PubMed...
    25. Magdolen P., Zahradník P., Foltínová P. (2000b): Synthesis, antimicrobial testing and QSAR study of new 2-phenylethenylbenzothiazolium salts substituted by cyclic amines. Pharmazie, 55: 803-810. Go to original source... Go to PubMed...
    26. Matsumoto K., Toda M., Hashimoto S. (1991): Selectivity in the consecutive snar-dequarternization reactions of heteroaromatic chlorides with tertiary amines under high pressure. Chemical Letters, 8: 1283-1286. Go to original source...
    27. Mitchell J.W., Livingston G.A. (1968): Methods of studying plant hormones and growth-regulating substances. Agriculture Handbook No. 336, Agricultural Research Service US Government Printing Office, Washington DC.
    28. Nivalkar K.R., Mashraqui S.H. (1996): Condesation of thioamides with 2-aminothiophenols: A versatile synthesis of benzothiazoles. Synthetic Communication, 26: 3535-3542. Go to original source...
    29. Olson W.A., Nalewaja J.D., Schroeder G.L., Duysen M.E. (1981): Diclofop and MCPA influence on coleoptile growth. Weed Science, 29: 597-600. Go to original source...
    30. Osborne D.J., Hallaway M. (1960): Auxin control of protein levels in detached autumm leaves. Nature, 188: 240-241. Go to original source...
    31. Osborne D.J., McCalla D.R. (1961): Rapid bioassay for kinetin and kinins using senescing leaf tissue. Plant Physiology, 36: 219-221. Go to original source... Go to PubMed...
    32. Pan R., Zhao Z. (1994): Synergistic effects of plant growth retardants and IBA on the formation of adventitious root in hypocotyl cutting of mung beang. Plant Growth Regulation, 14: 15-19. Go to original source...
    33. Procházka S., Šebánek J. (1997): Regulátory růstu rostlin. Academia, Praha.
    34. Pulkrábek J., Šroller J., Zahradníček J. (1999): The effect of growth regulators on the yield and quality of sugar beet roots. Rostlinná Výroba, 45: 379-386.
    35. Richmond A.E., Lang A. (1957): Effect of kinetin on protein content and survival of detached Xanthium leaves. Science, 125: 650-651. Go to original source... Go to PubMed...
    36. Satler S.O., Thimann K.V. (1980): The influence of aliphatic alcohols on leaf senescence. Plant Physiology, 66: 395-399. Go to original source... Go to PubMed...
    37. Sekerka V., Štefáková E., Sutoris V. (1989): 3-benzyloxykarbonylmetyl-2-benzothiazolinón - nový potenciálny stimulátor rastu rastlín. Poľnohospodárstvo, 35: 593-603.
    38. Shimabukuro M.A., Shimabukuro R.H., Nord W.S., Hoerauf R.A. (1978): Physiological effects of methyl 2-[4(2,4-dichlorophenoxy)-phenoxy] propanoate on oat, wild oat and wheat. Pesticide Biochemistry and Physiology, 8: 199-207. Go to original source...
    39. Sirois J.C. (1966): Studies on growth regulators. I: Improved Avena coleoptile elongation test for auxin. Plant Physiology, 41: 1308-1312. Go to original source... Go to PubMed...
    40. Sutoris V., Gáplovský A., Sekerka V. (1993): Benzothiazole compounds. XLVI. 3,4 disubstituted 2-benzothiazolinones with plant growth regulation activity. Chemical Papers, 47: 260-263.
    41. Thomas J.C., Katterman F.R. (1986): Cytokinin activity induced by thidiazuron. Plant Physiology, 81: 681-683. Go to original source... Go to PubMed...
    42. Vernon L.P. (1960): Spectrophotometric determination of chlorophylls and pheophytins in plant extract. Analytical Chemistry, 32: 1144-1150. Go to original source...

    This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.


    Return to the content