Journal of Plant Growth Regulation

, Volume 23, Issue 4, pp 280–291 | Cite as

Synthesis and Biological Activity of Urea and Thiourea Derivatives from 2-Aminoheterocyclic Compounds

  • P. A. Yonova
  • G. M. Stoilkova


Thirty-eight N-substituted-N′-(2-thiazolyl and furfuryl)ureas and thioureas were prepared by reaction of 2-aminothiazole and 2-furfurylamine with the appropriate iso(thio)cyanate. All compounds were tested for herbicidal activity and selectivity on seedlings of wheat (a monocotyledonous plant) and cucumber (a dicotyledonous plant). Only one compound (1) out of 14 ureas was characterized by considerable herbicidal activity against the wheat seedlings and two compounds (1 and 2) - towards the cucumber seedlings. The phenylurea derivative of 2-aminothiazole (1) was 1.7-fold more and the 3-chlorophenylurea derivative of 2-furfurylamine (23) was equally as active as the standard diuron with respect to selective herbicidal activity. Among 24 thioureas, four compounds (15,16,17, and 18) to displayed the highest selective herbicidal activity and two other compounds (19 and 33) were almost equal to diuron activity. Selective herbicidal ratio (SHR) represents the degree of herbicidal effect of the investigated compounds compared to diuron at both test objects. Four compounds (16,17,18, and 23) possessed SHR << 100 in the wheat seedlings while in the cucumber seedlings they had SHR >> 100. Therefore these compounds were substantially more active herbicides to the wheat seedlings as compared to diuron. The cytokinin-like activity of the synthesized compounds was also investigated in terms of betacyanin synthesis and radish cotyledon enlargement. The urea derivatives exhibited mostly high cytokinin-like activity but their activity remained lower than those of kinetin and N-phenyl-N′-(4-pyridyl)urea. The N-(3-fluorophenyl)-N′-(2-thiazolyl)urea (2) possessed the greatest activity at 10 μM while the corresponding compound with 3-chlorophenyl (4) was the most active cytokinin-like substance in the whole concentration range tested. Attention was also given to structure-activity relationships for the screened compounds. In general, the ureas and thioureas containing a 2-thiazole ring were more active than those containing a 2-furfuryl residue.


Cytokinin Herbicide Synthesis Thiourea Urea 



We sincerely thank Dr. N. G. Vassilev (Institute of Organic Chemistry, BAS, Bulgaria) for recording the NMR spectra and National Foundation for Scientific Research of Bulgaria for financial support. We also thank Mrs. S. Samurova (Department of Chemistry, University of Sofia, Bulgaria) for providing CHN-analyses data.


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Copyright information

© Springer-Verlag 2005

Authors and Affiliations

  1. 1.Institute of Plant PhysiologyBulgarian Academy of SciencesBulgaria

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