Abstract
Twenty-eight Cl-substituted diphenylurea derivatives differing in either the number and the position of the substituents, or in the type of substitution, that is, symmetric or asymmetric, were synthesized. Their hypothetical enhancement of rooting activity was assayed using the mung bean shoot bioassay; their possible cytokinin-like activity was assesed using the betacyanin (so-called “amaranthin”) accumulation test and the tomato regeneration test. Seven Cl-substituted diphenylurea derivatives (2E, 4A, 4B, 4E, 4G, 6A, 6B) having two substituted phenyl rings showed the capacity to enhance adventitious root formation in mung bean shoots. Furthermore the presence of a halogen substituent was not sufficient to reach the adventitious rooting activaties shown by the N,N′-bis-(2,3-methylenedioxyphenylurea) and the N,N′-bis-(3,4-methylenedioxyphenylurea), two diphenylurea derivatives for which an interaction with auxin was the first reported in enhancing adventitious root formation. Seven compounds (1B, 3E, 3D, 4B, 4E, 4F, 6B) showed cytokinin-like activity and three of them (4B, 4E, 6B) also evidenced rooting activity, once more demonstrating the wide action spectrum of diphenylurea derivatives.
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References
Arrieta A, Palomo C. 1981. Phosphorus in organic chemistry. Part. II. A new method of preparingN-N′ disubstituted aryl ureas using phenyl N′-phenylphosphoramidoazidate reagent Tetrahedron Lett 2218:1729–1732.
Beaver DJ, Roman DP, Stoffel PJ. 1957. Preparation and bacteriostatic activity of substituted ureas. J Am Chem Soc 79:1236–1245
Branca C, Torelli A, Bassi M. 1990. Effects of benzisothiazole on tomato plant regenerationin vitro. Plant Cell Tiss Org Cult 21:17–19
Briody JM, Narinesingh D. 1977. Ortho-effecgs in the acylation of substituted phenylureas with isocyanates and acetic anhydride J Chem Soc, Perkin Transaction 2: Phys Org Chem 7:934–939.
Bruce MI, Zwar JA. 1966. Cytokinin activity of some substituted ureas and thioureas. Proc R Soc 165:245–265.
Buu-Hoi NgPh, Xuong NgD, Suu VT. 1958 NewN,N′-disubstituted thioureas and ureas of biological interest (abstract) J. Chem. Soc.:2815–2821.
De Klerk GJ, De Hanecakova J, Jasik J. 2001. The role of cytokinins in rooting of stem slices cut from apple microcuttings. Plant Biosystems 1351:79–84.
Dondoni A, Barbaro G, Battaglia A. 1977. Synthesis of 1,2,3,5-oxathiadiazole 2-oxides from amidoximes and thionyl chloride and the mechanism of their thermally induced fragmentation and rearrangement to carbidiimides. J Org Chem 4221:3372–3377.
Fahmy AFM, Esawy SA. 1973. Acid azides II. Reactions of acid azides with hydrazides, amides, and amino acids. Indian J Chem 119:871–873.
Georges LW, Hamalainen C. 1949. Some new polyhalogenated phenyl isocyanates. J Am Chem Soc 71:743–744.
Hongu T, Osaki S. 1962. Syntheses and ultraviolet absorption spectra of phenylurea derivatives. Nippon Kagaku Zasshi 83:816–819.
Iwamura H, Fujita T, Koyama S, Koshimizu K, Kumazawa Z. 1980. Quantitative structure-activity relationship of cytokinin-active adenine and urea derivatives. Phytochemistry 197:1309–1319.
Katritzky AR, Nie P-L, Dondoni A, Tassi D. 1977. A new synthesis of diaryl carbodiimides. Synth Commun. 76:387–392.
Kevers C, Hausman JF, Faivre-Rampant O, Evers D, Caspar T. 1997. Hormonal control of adventitious rooting: progress and questions. Angew Bot 71:71–79.
Kutepov DF, Potashnik AA, Rozanova NS. 1959. Synthesis and transformations of diarylurea series. IX. Synthesis of unsymmetric nuclearly chloro-substituted di-phenylureas. Zurnal Obshchei Khimii 29:3036–3038.
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.
Mok MC, Mok DWS, Turner JE, Mujer CV. 1987. Biological and biochemical effects of cytokinin-active phenylurea derivatives in tissue culture systems. Hort Science 22:1194–1197.
Mok MC, Mok DWS. 1985. The metabolism of [14C]-thidiazuron in callus cultures ofPhaseolus lunatus. Physiol Plant 65:427–432.
Murashige T, Skoog F. 1962. A revised medium for rapid growth and bioassay with tobacco tissue cultures. Physiol Plant 15:473–497.
Ramadas K, Janarthanan N. 1977. New synthetic strategy for urea herbicides. Synthetic Commun 2713:2357–2362.
Ricci A, Carra A, Torelli A et al. 2001a. Cytokinin-like activity of N′-substituted N-phenylureas. Plant Growth Regulation 34:167–172.
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 Mill. Plant Science 1605: 1055–1065.
Ricci A, Carra A, Rolli E, Bertoletti C, Branca C. 2003. 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 Regulation 40:207–212.
Romanov GA, German IA, Schmulling T. 2000. Investigation of early cytokinin effects in a rapid Amaranthus seedling test. Plant Growth Regul 32:337–344.
Salituro F, Gerald B, Guy W, Green J, Kofron JL. 1999. Preparation of urea derivates as inhibitors of p38. PCT Int. Appl. (1999), 93 pp WO 9900357 (Patent numbre).
Schmitz RY, Skoog F. 1970. The use of dimethylsulfoxide as a solvent in the tobacco bioassay for cytokinins. Plant Physiol 45:537–538
Scholz, H. Oxazolidine-2,4-diones. Ger. Offen. (1980), 8 pp DE2827414 (Patent number).
Shantz EM, Steward FC. 1955. The identification of compound A from coconut milk as 1,3-diphenylurea. J Am Chem Soc 77:6351–6353.
Shudo K. 1994. Chemistry of phenylurea cytokinins. In: Mok DWS, Mok MC. Cytokinins-chemistry, activity and function Boca Raton: CRC Press, pp. 35–42.
Sonnenschein H, Schmitz E. 1989. Ureas fromN-chloroamidines: an aza-analogous Hofmann degradation. Synthesis 6:433–444.
Spryskov AA, Solodushenkov SN, Klyuev VN. 1957. Synthesis and uses of carbanilide derivatives. I. Preparation of symmetrical 4,4′-dinitrocarbanilides. Zhur Priklad Khim (Sankt-Peterburg, Russian Federation) 30:1130–1134.
Takahashi S, Shudo K, Okamoto T, Yamada K, Isogai Y. 1978. Cytokinin activity of N′-phenyl-N′-(4-pyridil)urea derivatives Phytochemistry 17:1201–1207.
Thompson HE, Swanson CP, Norman AG. 1946. New growth-regulating compounds. I. Symmary of growth-inhibitory activities of some organic compounds as determined by three tests Botan Gaz (Chicago) 107:476–507.
Yang Y, Lu S. 1999. Selenium-catalyzed reductive carbonylation of nitrobenzene with amines as coreagents to give unsymmetric phenylureas. Tetrahedron Lett 4026:4845–4846.
Zinner G, Gruenefeld J. 1985. Syntheses, reactivities, and spectroscopic properties of chloroformamines from squaric acid dichloride Arch Pharm (Weinheim, Germany) 31811:992–998.
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Online publication: 17 March 2005
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Ricci, A., Carra, A., Rolli, E. et al. Effect of Cl-substitution on rooting-or cytokinin-like activity of diphenylurea derivatives. J Plant Growth Regul 23, 261–268 (2004). https://doi.org/10.1007/BF02637249
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DOI: https://doi.org/10.1007/BF02637249