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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
Article

Abstract

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.

Keywords

Cytokinin Herbicide Synthesis Thiourea Urea 

Notes

Acknowledgments

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.

References

  1. Arndt, Fr, Schulz, H, Rusch, R (1977) “Composition containing 1,2,3-thiadiazolylurea for defoliating plants” Ger Offen 2 506 960Google Scholar
  2. Basarab, GS, Pifferitti, M, Bolinski, M 1991The chemistry and biological activity of a new class of azole fungicidesPestic Sci31403417Google Scholar
  3. Biddington, NL, Thomas, TH 1973A modified Amaranthus betacyanins bioassay for the rapid determination of cytokinin in plant extractsPlanta (Berl.)111183186Google Scholar
  4. Burkard, W, Rheiner, A, Richle, R (1972) “Antimalarial thiazolylthioureas” U S 3767 804, 1971. Ger. Offen. 2 137 045Google Scholar
  5. Cavender, PL, Green, CM, Mack, SB 1988Antisenescence activity of 4,5-disubstituted imidazoles: new cytokinin mimicsJ Agric Food Chem3610761079CrossRefGoogle Scholar
  6. Chen, H, Li Zh, , Han, Y 2000Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl(alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles)J Agric Food Chem4853125315CrossRefPubMedGoogle Scholar
  7. Creuzburg, D, Kleiner, R, Klepel, M, Gross, M 1977Growth regulating properties of substituted pyrazolyl-phenyl ureas. Int. Conf. on Regulation of Developmental Processes in Plants.Abstracts Halle (Ger.).228Google Scholar
  8. Darlington, A, Vishnevetskaia, K, Blake, TJ 1996Growth enhancement and antitranspirant activity following seed treatment with a derivative of 5-hydroxybenzimidazole (Ambiol) in four drought-stressed agricultural speciesPhysiol Plant97217222CrossRefGoogle Scholar
  9. Dayan, FE, Vincent, AC, Romagni, JG,  et al. 2000Amino- and urea-substituted thiazoles inhibit photosynthetic electron transferJ Agric Food Chem4836893693CrossRefPubMedGoogle Scholar
  10. Dowding, J, Leeds, WG (1971) “Herbicidal haloureidothiazoles” Ger Offen 2 040 580Google Scholar
  11. Durga, DN, Ramesh, MC 1974Synthesis and specrtoscopic studies of N-aryl-N′-2-thiazolyl-thoureasZ Narurforsch Teil B29408409Google Scholar
  12. Gheorghiu, P, Marcu, C, Bratu, V,  et al. 1962Antituberculous activity of certain new thiourea derivativesFarmacia (Bucharest)10229233Google Scholar
  13. Goure, WF, Leschinsky, KL, Wratten, SJ, Chupp, JP 1991Synthesis and herbicidal activity of N-substituted 2,6-bis(polyfluoromethyl)dihydropyridine-3,5-dicarboxylatesJ Agric Food Chem39981986CrossRefGoogle Scholar
  14. Henrie, II RN, Green, CM, Yeager, WH, Ball, III TF 1988Activity optimization of pyridinyl N-oxide urea cytokinin mimicsJ Agric Food Chem36626633CrossRefGoogle Scholar
  15. Irem, SO, Smith, JR, Chanana, GD 1990Evidence for sulfation of 1-phenyl-3-(2-thiazolyl)-2-thioureaProc. West Pharmacol Soc33199203PubMedGoogle Scholar
  16. Isogai, Y. (1981) “Cytokinin activities of N-phenyl-N′-(4-pyridyl)ureas” In: Guern, J, Peaud-Lenoel, C (eds.), Metabolism and molecular activities of cytokinins, Springer-Verlag, Berlin, pp 115Google Scholar
  17. Iwamura, H, Masuda, N, Koshimizu, K, Matsubara, S 1979Cytokinin-agonistic and antagonistic activities of 4-substituted-2-methylpyrrolo[2,3-d]pyrimidmes, 7-deaza analogs of cytokinin-active adenine derivativesPhytochemistry18217222CrossRefGoogle Scholar
  18. Kano, S, Hagiwara, K, Sato, T, Ando, M, Hashimoto, J “Thiazolylthiourea derivatives, acaricides and insecticides” Japan Kokai 7796, 739Google Scholar
  19. Kefford, NP, Bruce, MI, Zwar, JA 1966Cytokinin activities of phenylurea derivatives—bud growthPlanta68292296CrossRefGoogle Scholar
  20. Kerr, JS, Boswell, GA 1992N-[2-(2-oxo-l-imidazolidinyl)ethyl]-3-phenyl-urea and analogs as agents for induction of antioxidant enzymesChem Abstr116P728gGoogle Scholar
  21. Kumar, N, Mittal, PS, Taneja, AP, Kudesia, VP 1989Synthesis of potential fungicides and nematocides; thiazolyl thiocarbamidesActa Cienc Indica Chem15265270Google Scholar
  22. Lee, EH, Chen, CM 1982Studies on the mechanisms of ozone tolerance: cytokinin-like activity of N-[2-(2-oxo-l-imidazolidinyl)ethyl]-N′-phenylurea, a compound protecting against ozone injuryPhysiol Plant56486491Google Scholar
  23. Lee, EH, Bennett, JA 1985Superoxide dismutase: A possible protective enzyme against ozone injury in snapbeans (Phaseolus vulgaris L.)Physiol Plant76479484Google Scholar
  24. Letham, DS 1971Regulators of cell division in plant tissues. XII. A cytokinin bioassay using excised radish cotyledonsPhysiol Plant25391396Google Scholar
  25. Mallipudi, NM, Lee, A, Kapoor, IP, Hollingsaus, GJ 1994Synthesis and insecticidal activity of novel N-oxalyl-N-methylcarbamatesJ Agric Food Chem4210191025CrossRefGoogle Scholar
  26. Mishra, AR, Singh, S, Wahab, A 2000Antifungal activity of new 1,3,4-oxadiazolo[3,2-a]-s-triazine-5,7-diones and their 5-thioxo-7-onesJ Agric Food Chem4854655468CrossRefPubMedGoogle Scholar
  27. Mok, MC, Mok, DWS, Armstrong, DJ, Shudo, K, Isogai, Y, Okamoto, T 1982Cytokinin activity of N-phenyl-N′-(1,2,3-thiadiazol-5-yl)urea (thidiazuron)Phytochemistry2115091511CrossRefGoogle Scholar
  28. Nishikawa, S, Kurono, M, Shibayama, K, Okuno, S, Inagaki, M, Kashimura, N 2000Synthesis and cytokinin activity of fluorescent 7-phenylethynylimidazo[4,5-b]pyridine and its ribosideJ Agric Food Chem4825592564CrossRefPubMedGoogle Scholar
  29. Okamoto, T, Shudo, K, Isogai, Yo (1983) “Structural and biological links between urea and purine cytokinins” In: Miyamoto, J, Kearney, PC (eds.), lupac pesticide chemistry (vol 1) Human welfare and the environment, Pergamon Press, pp 333-338Google Scholar
  30. Pevarello, P, Orsini, P, Traquandi, G,  et al. 20013(5)-Acylaminopyrazole derivatives: process for their preparation and their use as antitumor agentsChem (abstract)134P178552eGoogle Scholar
  31. Qian, X 1999Quantitative studies on structure-activity relationship of sulfonylurea and benzoylphenylurea type pesticides and their substituents’ bioisosterism using Synthons’ activity contributionJ Agric Food Chem4744154418CrossRefPubMedGoogle Scholar
  32. Santrucek, M, Krepelka, J 1988Antioxidants - potential chemotherapeutic agentsDrugs Future13974996Google Scholar
  33. Sasse, K, Braden, R, Eue, L, Hack, H (1969) “Furfurylurea herbicides” Pat S African 69 00 256Google Scholar
  34. Smirnov, LD, Kuznetsov, YV, Apasheva, LM,  et al. 19844-Aminomethyl derivatives of 2-methyl-5-hydroxy-benzimidazole with growth stimulating activityChem (abstract)101P186147kGoogle Scholar
  35. Steel, RGD, Torrie, JH. 1960Principles and procedures of statistics with special reference to the biological sciencesMcGraw-Hill Book Company, Inc.New York, Toronto, LondonGoogle Scholar
  36. Sumiyuki, A, Masayoshi, O 1967Antiviral activity of thiazole-thiourea derivativesYakugaku Zasshi8710061024PubMedGoogle Scholar
  37. Takahashi, S, Shudo, K, Okamoto, T, Yamada, K, Isogai Yo,  1978Cytokinin activity of N-phenyl-N′-(4-pyridyl)urea derivativesPhytochemistry1712011207CrossRefGoogle Scholar
  38. Teruhisa, N, Naoo, I, Yoshisuke, K, Saburo, K 1972Thiazole urea plant growth regulatorsJapan719214Google Scholar
  39. Vassilev, GN, Yonova, PA, Mihailov, VI, Raikov, ZD 1984Synthesis and biological activity of certain N-(2-chloroethyl)-N′-pyridyl and methylpyridylureasCompt Rend Acad Bulg Sci37811814Google Scholar
  40. Yonova, PA, Izvorska, ND, Lilov DTs, , Vassilev, GN, Belcheva, RN 1989Action of the synthetic cytokinins of the urea type on the growth and development of cytokinin-dependent tissue culturesCompt Rend Acad Bulg Sci42135138Google Scholar
  41. Zee-Cheng, RKJ, Cheng, CC 1979Antileukemic activity of substituted ureido-thiazoles, ureidothiadiazoles and related compoundsJ Med Chem222832CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag 2005

Authors and Affiliations

  1. 1.Institute of Plant PhysiologyBulgarian Academy of SciencesBulgaria

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