Synthesis and Biological Evaluation of 3,3-Dimethyl-1-(1H-1,2,4-triazole-1-yl)butan-2-One Derivatives as Plant Growth Regulators

Abstract

We synthesized nine novel triazole-compounds and investigated their plant growth regulatory activity. Compound CGR₃, with methoxyacyl on 3-position of triazole ring, showed better activity, promoting root length not only for mungbean, but also for wheat. Additionally, CGR3 changed the level of endogenous hormones in mungbean roots, the most obvious effect was the increase of IAA, being 4.9 times greater than that of the control at the 96th hour after treatment. Among the synthesized new 1,2,4-triazol derivatives, CGR₃ could be applied as a new agrochemical, functioning as a root growth stimulant, which promotes primary root length, influences the levels of endogenous hormones(IAA, ABA and GA₃) to play an important role in controlling the primary root development.

Keywords

1,2,4-Triazole derivatives / Plant growth regulatary activity / Roots

References

[1] Erhardt H., Mohr F., Kirsch S. F. Chemical Communications, 2015, 52(3): 545.

[2] Petrikkos G., Skiada A. International Journal of Antimicrobial Agents, 2007, 30(2): 108.

[3] Peng X. M., Cai G. X., Zhou C. H. Current Topics in Medicinal Chemistry, 2013, 13(16): 1963.

[4] Todoroki Y., Kobayashi K., Yoneyama H., Hiramatsu S., Jin M. H., Watanabe B., Mizutani M., Hirai N. Bioorganic & Medicinal Chemistry, 2008, 16(6): 3141.

[5] Asami T., Min Y. K., Nagata N., Yamagishi K., Takatsuto S., Fujioka S., Murofushi N., Yamaguchi I., Yoshida S. Plant Physiology, 2000, 123(1): 93.

[6] Saito S., Hirai N., Matsumoto C., Ohigashi H., Ohta D., Sakata K., Mizutani S. M. Plant Physiology, 2004, 134(4): 1439.

[7] Funaki Y., Oshita H., Tanaka S., Yamamoto S., Kato T. 1-Phenyl-2-azolyl-4,4-dimethyl-1-pentent-3-ols and the Fungicidal Use Thereof, 1980.

[8] Izumi K., Nakagawa S., Kobayashi M., Oshio H., Sakurai A., Takahashi N. Plant & Cell Physiology, 1998, 29(1): 97.

[9] Zhang M., Duan L., Tian X., He Z., Li J., Wang B., Li Z. Journal of Plant Physiology, 2007, 164(6): 709.

[10] Lucini L., Rouphael Y., Cardarelli M., Bonini P., Baffi C., Colla G. A. Frontiers in Plant Science, 2018, 9(472): 1.

[11] Saito S., Okamoto M., Shinoda S., Kushiro T., Koshiba T., Kamiya Y., Hirai N., Todoroki Y., Sakata K., Nambara E., Mizutani M. Bioscience Biotechnology & Biochemistry, 2006, 70(7): 1731.

[12] Okazaki M., Kittikorn M., Ueno K., Mizutani M., Hirai N., Kondo S., Ohnishi T., Todoroli Y. Bioorganic & Medicinal Chemistry, 2012, 20(10): 3162.

[13] Takeuchi J., Okamoto M., Mega R., Kanno Y., Ohnishi T., Seo M., Todoroki Y. Scientific Reports, 2016, 6: 37060.

[14] Kamran M., Su W., Ahmad I., Meng X., Cui W., Zhang X., Mou S., Khan A., Han Q., Liu T. Scientific Reports, 2018, 8(1): 4818.

[15] Hampton J. G., Hebblethwaite P. D. Grass For. Sci., 1985, 40: 93.

[16] Leul M., Zhou W. J. Journal of Plant Growth Regulation, 1999, 18(1): 9.

[17] Bengough A. G., Mckenzie B. M., Hallett P. D., Valentine T. A. Journal of Experimental Botany, 2011, 62(1): 59.

[18] Thole J. M., Beisner E. R., Liu J., Venkova S. V., Strader L. C. G3-Genes Genomes, 2014, 4(7): 1259.

[19] Sun H., Feng F., Liu J., Zhao Q. Frontiers in Plant Science, 2018, 9(659): 1.

[20] Postma J. A., Schurr U., Fiorani F. Biotechnology Advances, 2014, 32(1): 53.

[21] Meffre P., Durand P., Branquet E., Goffic F. C. L. Synthetic Communications, 1994, 24(15): 2147.

[22] Holmwood G., Regel E. Substituted Triazolylmethyl Oxiranes, Process for Their Preparation and Their Application as Intermediates, 1985.

[23] Cai G. R., Zhang D. F., Li B., Feng N. J. Chinese Journal Structure Chemistry, 2017, 36(4): 599.

[24] Stoilkova G. M., Yonova P., Ananieva K. Plant Growth Regulation, 2014, 72(3): 303.

[25] Kučerová D., Kollárová K., Zelko I., Vatehová Z., Lišková D. Journal of Plant Physiology, 2014, 171(7): 518.

[26] Segarra G., Jáuregui O., Casanova E., Trillas I. Phytochemistry, 2006, 67(4): 395.

[27] Reiter J., Pongó L., Dvortsák P. Journal of Heterocyclic Chemistry, 1987, 24(1): 127.

[28] Almajan G. L., Barbuceanu S. F., Saramet G., Almajan G. L., Draghici C., Barbuceanu F., Bancescu G. European Journal of Medicinal Chemistry, 2012, 49(31): 417.

[29] Stefanska J., Stepien K., Bielenica A., Szulczyk D., Miroslaw B. E., Koziol A., Sanna G., Luliano F., Madeddu S., Jozwiak M., Struga M. Medicinal Chemistry, 2016, 12(5): 478.

[30] Todoroki Y., Kobayashi K., Yoneyama H., Hiramatsu S., Jin M. H., Watanabe B., Mizutani M., Hirai N. Bioorganic & Medicinal Chemistry, 2008, 16(6): 3141.

[31] Raskin I. Annual Review of Plant Biology, 1992, 43(1): 439.

[32] Macmillan J., Ward D. A., Phillips A. L., Sánchezbeltrán M. J., Gaskin P., Lange T., Hedden P. Plant Physiology, 1997, 113(4): 1369.

[33] Wells D. M., French A. P., Naeem A., Ishaq O., Traini R., Hijazi H. I., Bennett M. J., Pridmore T. P. Philosophical Transactions of the Royal Society of London, 2012, 367: 1517.

[34] Jiang L., Cedrick M., Belen M. G., Carolien D. C., Lien S., Annick D. K., Franccedil B., Tom B., Stephen D., Sofie G. Journal of Experimental Botany, 2016, 67(1): 379.

[35] Yin C. C., Ma B., Collinge D. P., Pogson B. J., He S. J., Xiong Q., Duan K. X., Chen H., Yang C., Lu X., Wang Y. Q., Zhang W. K., Chu C. C., Sun X. H., Fang S., Chu J. F., Lu T. G., Chen S. Y., Zhang J. S. Plant Cell, 2015, 27(4): 1061.

[36] Fonseca S., Rosado A., Vaughan-Hirsch J. Frontiers in Plant Science, 2014, 5: 709.

[37] Koltai H., Dor E., Hershenhorn J., Joel D. M., Weininger S., Lekalla S., Shealtiel H., Bhattacharya C., Eliahu E., Resnick N., Barg R., Kapulnik Y. Journal of Plant Growth Regulation, 2010, 29(2): 129.

[38] Strader L. C., Chen G. L., Bartel B. Plant Journal, 2010, 64(5): 874.

[39] Desikan R., Cheung M., Bright J., Dan H., Hancock J. T., Neill S. J. Journal of Experimental Botany, 2004, 55(395): 205.

[40] Sah S. K., Reddy K. R., Li J. Frontiers in Plant Science, 2016, 7(571): 1.

[41] Muñoz-Espinoza V. A., López-Climent M. F., Casaretto J. A., Gómez-Cadenas A. Frontiers in Plant Science, 2015, 6(138): 997.