Skip to main content
Log in

Diheteroarylurea derivatives as adventitious rooting adjuvants in mung bean shoots and M26 apple rootstock

  • Original Paper
  • Published:
Plant Growth Regulation Aims and scope Submit manuscript

Abstract

The present research investigates the biological profile of eight symmetrical diheteroarylureas and phenylheteroarylureas, testing their hypothetical cytokinin-like activity and rooting activity. Cytokinin-like activity was assayed by the betacyanin (so-called amaranthin) accumulation test and by the tomato regeneration test. The rooting activity was assessed using the mung bean rooting test, the apple stem slice test and the rooting of apple microcuttings. Three compounds, 1,3-di(pyrazin-2-yl)urea (3a), 1,3-di(benzo[d]oxazol-5-yl)urea (3b) and 1,3-di(benzo[d]oxazol-6-yl)urea (3c), enhanced adventitious root formation in apple stem slice test, but only 3b and 3c were active in the mung bean rooting test. Compound 3b, that showed the best rooting activity, was also able to enhance the adventitious root formation in apple microcuttings. None of the compounds showed cytokinin-like activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Bo YY, Chackrabarti PP, Chen N, Doherty EM, Fotsch CH, Han N, Kelly MG, Liu Q, Norman MH, Wang X (2003) Preparation of vanilloid receptor ligands and their use in treatments. PCT Int Appl, pp 611. WO 2003049702

  • Bottomley W, Kefford NP, Zwar JA, Goldacre PL (1963) Kinin activity from plant extracts. Aust J Biol Sci 16:395–409

    CAS  Google Scholar 

  • Boyle RG, Imogai HJ, Cherry M (2003) Preparation of diarylureas as Chk-1 Kinase inhibitors for the treatments of cancer. PCT Int Appl, pp 83. WO 2003101444

  • Branca C, Bucci G, Domiano P, Ricci A, Torelli A, Bassi M (1991) Auxin structure and activity on tomato morphogenesis in vitro and pea stem elongation. Plant Cell Tiss Org Cult 24:105–114

    Article  CAS  Google Scholar 

  • Branca C, Maggiali CA, Morini G, Ronchino F, Ricci D, Scoccianti V (1987) Synthesis and cytokinin-like activity of 7-chloro-imidazo[1,2-c]pyrimidines. Phytochemistry 26:25–29

    Article  Google Scholar 

  • Branca C, Plazzi V, Vitto M, Bordi F, Serafini-Fracassini D, Bagni N (1975) Auxin-like activity of 1,2-benzisothiazole derivatives. Phytochemistry 14:2545–2550

    Article  CAS  Google Scholar 

  • Branca C, Torelli A, Bassi M (1990) Effects of benzisothiazole on tomato plant regeneration in vitro. Plant Cell Tiss Org Cult 21:17–19

    Article  CAS  Google Scholar 

  • Brandstatter I, Kieber JJ (1998) Two genes with similarity to bacterial response regulators are rapidly and specifically induced by cytokinin in Arabidopsis. Plant Cell 10:1009–1020

    Article  PubMed  CAS  Google Scholar 

  • Chan G, Johns A, Jurewicz A, Porter RA, Widdowson K (1999) Preparation of quinolinylureas and related compounds as HFGAN72 antagonists. PCT Int Appl, pp 64. WO 9909024

  • Chieda GB, Hong C (1971) II Synthesis of naturally occurring 6-ureidopurines and their nucleosides. J Med Chem 14:748–753

    Article  Google Scholar 

  • De Klerk GJ, Caillat E (1994) Rooting responses of stem-disks excised from the same “M9 Jork” microcutting. Adv Hort Sci 8:15–18

    Google Scholar 

  • Dey S, Garner P (2000) Synthesis of tert-butoxycarbonyl (Boc)-protected purines. J Org Chem 65(22):7697–7699

    Article  PubMed  CAS  Google Scholar 

  • El-Kerdawy MM, Tantawi AS, Massoud MAM, Abou-zeid LA (1999) Synthesis and antithyroid activity of certain uracil and thiouracil derivatives. Alexandria J Pharm Sci 13:121–125

    CAS  Google Scholar 

  • Gravestock MB (2000) Preparation of new [(heterocyclylamino)methyl]oxazolidinones as antibacterials. PCT Int Appl, pp 148. WO 2000021960

  • Haberer G, Kieber JJ (2002) Cytokinins. New insights into a classic phytohormone. Plant Physiol 128:354–362

    Article  PubMed  CAS  Google Scholar 

  • Hedayatullah M, Challier A, Lion C (1997) Reaction of phenyl isocyanate with cytosine, thymine, uracil, adenine and guanine. Bull Soc Chim Belges 106:115–177

    CAS  Google Scholar 

  • Miller CO (1960) Proceedings of the plant physiology meetings. Plant Physiol 35:xxvi

    Google Scholar 

  • Mok MC, Kim SG, Armstrong DJ, Mok DWS (1979) Induction of cytokinin autonomy by N,N′-diphenylurea in tissue cultures of Phaseolus lunatus L. Proc Natl Acad Sci 76:3880–3884

    Article  PubMed  CAS  Google Scholar 

  • Mok MC, Mok DWS, Armstrong DJ, Shudo K, Isogai Y, Okamoto T (1982) Cytokinin activity of N-phenyl-N′-1,2,3-thiadiazol-5-ylurea (thidiazuron). Phytochemistry 21:1509–1511

    Article  CAS  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassay with tobacco tissue cultures. Physiol Plant 15:473–497

    Article  CAS  Google Scholar 

  • Ricci A, Carra A, Maggiali CA, Incerti M, Branca C (2003a) Weakly cytokinin-active diphenylurea derivatives influence adventitious rooting in M26 Malus pumila microcuttings. Plant Growth Regul 39:19–26

    Article  CAS  Google Scholar 

  • Ricci A, Carra A, Rolli E, Bertoletti C, Branca C (2003b) N,N′-bis-(2,3-methylenedioxyphenyl)urea and N,N′-bis-(3,4-methylenedioxyphenyl)urea cooperate with auxin in enhancing root formation of M26 apple (Malus pumila Mill.) stem slices. Plant Growth Regul 40:207–212

    Article  CAS  Google Scholar 

  • Ricci A, Carra A, Rolli E, Bertoletti C, Morini G, Incerti M, Vicini P (2005) Effect of Cl-substitution on rooting or cytokinin-like activity of diphenylurea derivatives. J Plant Growth Regul 23:261–268

    Article  CAS  Google Scholar 

  • Ricci A, Carra A, Torelli A, Maggiali CA, Morini G, Branca C (2001b) Cytokinin-like activity of N,N′-diphenylureas. N,N′-bis-(2,3-methylenedioxyphenyl)urea and N,N′-bis-(3,4-methylenedioxyphenyl)urea enhance adventitious root formation in apple rootstock M26 (Malus pumila). Plant Sci 160:1055–1065

    Article  CAS  Google Scholar 

  • Ricci A, Carra A, Torelli A, Maggiali CA, Vicini P, Zani F, Branca C (2001a) Cytokinin-like activity of N′-substituted N-phenylureas. Plant Growth Regul 34:167–172

    Article  CAS  Google Scholar 

  • Romanov GA, Getman IA, Schmulling T (2000) Investigation of early cytokinin effects in a rapid Amaranthus seedling test. Plant Growth Regul 32:337–344

    Article  CAS  Google Scholar 

  • Schmitz RY, Skoog F (1970) The use of dimethylsulfoxide as a solvent in the tobacco bioassay for cytokinins. Plant Physiol 45:537–538

    Article  PubMed  CAS  Google Scholar 

  • Shantz EM, Steward FC (1955) The identification of compound A from coconut milk as 1,3-diphenylurea. J Am Chem Soc 77:6351–6353

    Article  CAS  Google Scholar 

  • Shudo K (1994) Chemistry of phenylurea cytokinins. In: Mok DWS, Mok MC (eds) Cytokinins-chemistry, activity and function. CRC Press, Boca Raton, pp 35–42

    Google Scholar 

  • Stanovnik B, Tisler M, Golob V, Hvala I, Nikolic O (1980) Heterocycles. CXCVIII. Heteroacyl azides as acylating agents for aromatic or heteroaromatic amines. J Het Chem 17:733–736

    Article  CAS  Google Scholar 

  • Van der Krieken WM, Breteler H, Visser MHM, Mavridou D (1993) The role of the conversion of IBA into IAA on root regeneration in apple: introduction of a test system. Plant Cell Rep 12:203–206

    Article  Google Scholar 

  • Vicini P, Incerti M, Maggiali CA, Ricci A, Rolli E (2003) Convenient synthetic procedure for the preparation of nitrogen/oxygen containing heteroarylureas interesting as plant growth regulators. In: Kartsev VG (ed) Oxygen and sulfur containing heterocycles. Proceedings of II International conference on the chemistry and biological activity of oxygen- and sulfur-containing heterocycles, vol 1, 14–17 October 2003, Moscow (Russia), IBS Press, Moscow, p 465

  • Werner T, Motyka V, Laucou V, Smets R, Van Onckelen H, Schmulling T (2003) Cytokinin-deficient transgenic Arabidopsis plants show multiple development alterations indicating opposite functions of cytokinins in the regulation of shoot and root meristem activity. Plant Cell 15:2532–2550

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

We thank Dr. A. Scott-Monkhouse for her linguistic revision of the article. The research was supported by MIUR (Ministero dell’Istruzione, dell’Università e della Ricerca).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Ricci.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ricci, A., Incerti, M., Rolli, E. et al. Diheteroarylurea derivatives as adventitious rooting adjuvants in mung bean shoots and M26 apple rootstock. Plant Growth Regul 50, 201–209 (2006). https://doi.org/10.1007/s10725-006-9119-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10725-006-9119-1

Keywords

Navigation