Design, synthesis and biological activities of novel urea derivatives with superior plant growth-inhibiting activity

  • PDF / 818,048 Bytes
  • 10 Pages / 595.276 x 790.866 pts Page_size
  • 65 Downloads / 214 Views

DOWNLOAD

REPORT


ORIGINAL PAPER

Design, synthesis and biological activities of novel urea derivatives with superior plant growth‑inhibiting activity Zhikun Yang1 · Linghui Zhu1 · Hao Tian1 · Jine Wang1 · Jiaming Yin1 · Liusheng Duan1 · Weiming Tan1 Received: 10 July 2019 / Accepted: 16 November 2020 © Springer Nature B.V. 2020

Abstract In order to discover novel plant growth regulators and herbicides with new modes of action for crops production management and improvement, a series of new urea derivatives were designed and synthesized. The bioassay results demonstrated that target compounds exhibited remarkable inhibitory activities in the growth of hypocotyls and taproots and good promoting activity in the generation of lateral roots on Arabidopsis and rice, and compound Y9k showed considerable inhibition effects on germination of Bidens and growth of Abutilon in the herbicidal assay. These results suggested that compound Y9k may be a potential lead structure as a novel plant growth regulator for plant type regulation and weed control. Keywords  Urea derivatives · Arabidopsis · Rice · Plant growth-inhibiting activity · Herbicidal activity

Introduction Plant hormones are indispensable substances in the regulation of plant growth, development, and reproduction (Corné et al. 2012). They have been used in agricultural industry as the plant growth regulators (PGRs) to meet human’s demands for regulating plant growth and development for many years (Fahad et al. 2015). Many plant growth regulators including cycocel, uniconazole, mepiquat chloride (Fig. 1), have been applied to regulate crop phenotype based on GAs biosynthesis inhibition, which plays a vital role in solving the agricultural problems resulted from the overgrowth and lodging of crop (Soltanloo et al. 2018; Tan 2012; Tung et al. 2018). However, the growth retardants show manifest disadvantages of reducing leaf area and inhibiting root growth when they decreased plant height (Agehara and Leskovar 2015), and some PGRs also have further negative effects such as high residue and difficult degradation (Bauer et al. 2018). Obviously, it is an urgent demand to develop the novel growth retardants. Gibberellins (GAs), the key phytohormones in regulating plant height, have complex chemical structure (Fig. 1) as a tetracyclic diterpenoid natural product (Eugenio et al. * Weiming Tan [email protected] 1



College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, People’s Republic of China

2014; James et al. 1980) and multiple functions in regulating many developmental processes such as seed germination, root and shoot elongation, flowering and fruit patterning (Petracek et al. 2013; Shani et al. 2013). Meanwhile, the new growth retardants based on GAs’ chemical structure are also being developed, such as exo-16, 17-dihydro-gibberellin A5-13-acetate ­(DHGA5) (Beck et al. 2004) and compound 10d and 10f (Fig. 1) (Tian et al. 2017), they both present good retardation activities, but their chemical structure is still complicated, which makes it difficult to c