Login Register Cart 0
Generic placeholder image

Letters in Drug Design & Discovery

Editor-in-Chief

ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

Back
Research Article

Synthesis and Herbicidal Activities of Novel Thiazole PPO Inhibitors

Author(s): Shu Chen, Guihua Ren, Dan Pei, Fan Zhang, Jie Liu, Donglin Zhang, Ren Yang, Jianjun Shi, Tianming Xu and Chengxia Tan*

Volume 17, Issue 2, 2020

Page: [192 - 198] Pages: 7

DOI: 10.2174/1570180816666190329221521

Price: $65

Abstract

Background: Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a key enzyme in the biosynthesis of chlorophyll and heme, also the target of different types of herbicides. Thiazole compounds shown excellent biological activity, can be designed by using active groups docking for new PPO inhibitors.

Objective: The objective of this study was to synthsize a series of aryl thiazole compounds as PPO inhibitors.

Methods: In this study, a series of aryl thiazole compounds derivatives 11a-l were obtained from 2- chloro-5-nitrobenzoic acid as the starting material via esterification, Iron powder reduction, diazotization, Hantzsch reaction and final acylation. All synthesized compounds have been tested for their herbicidal activities as a PPO inhibitors.

Results: The Petri dish test indicated that all compounds exhibited good herbicidal activities at 200 mg/L using culture dish. And the post-emergence tests showed that at 150g.ai/ha on weed stem leaf spray treatment, some of the title compounds exhibited 80% inhibition rate against the dicotyledonou weeds Amaranthus retroflexus and Eclipta prostrate.

Conclusion: Good activity was noted for some compounds that compounds 11a, 11b, 11c, 11g, 11h had 80% inhibition on stems and leaves of Amaranthus retroflexus at 150g.ai/ha.

Keywords: Thiazole, PPO, inhibitors, herbicidal activity, amaranthus retroflexus, eclipta prostrate.

« Previous Next »
Graphical Abstract

[1]
Poulson, R.; Polglase, W.J. The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX. Protoporphyrinogen oxidase activity in mitochondrial extracts of Saccharomyces cerevisiae. J. Biol. Chem., 1975, 250(4), 1269-1274.
[PMID: 234450]
[2]
Duke, S.O.; Nandihalli, U.B.; Lee, H.J.; Duke, M.V. Protoporphyrinogen oxidase as the optimal herbicide Site in the porphyrin pathway. ACS Symp. Ser., 1994, 559, 191.
[http://dx.doi.org/10.1021/bk-1994-0559.ch014]
[3]
Wang, D.W.; Li, Q.; Wen, K.; Ismail, I.; Liu, D.D.; Niu, C.W.; Wen, X.; Yang, G.F.; Xi, Z. Synthesis and herbicidal activity of pyrido[2,3-d]pyrimidine-2,4-dione-benzoxazinone hybrids as novel protoporphyrinogen oxidase inhibitors. J. Agric. Food Chem., 2017, 65(26), 5278-5286.
[http://dx.doi.org/10.1021/acs.jafc.7b01990] [PMID: 28616976]
[4]
Hao, G.F.; Zuo, Y.; Yang, S.G.; Yang, G.F. Protoporphyrinogen oxidase inhibitor: An ideal target for herbicide discovery. Chimia (Aarau), 2011, 65(12), 961-969.
[http://dx.doi.org/10.2533/chimia.2011.961] [PMID: 22273380]
[5]
Zuo, Y.; Wu, Q.; Su, S.W.; Niu, C.W.; Xi, Z.; Yang, G.F. Synthesis, herbicidal activity, and QSAR of novel N-Benzothiazolyl- pyrimidine-2,4-diones as protoporphyrinogen oxidase inhibitors. J. Agric. Food Chem., 2016, 64(3), 552-562.
[http://dx.doi.org/10.1021/acs.jafc.5b05378] [PMID: 26728549]
[6]
Nam, K.H.; Park, K.W.; Han, S.M.; Kim, S.W.; Lee, J.H.; Kim, C.G. Compositional analysis of protoporphyrinogen oxidase-inhibitingherbicide-tolerant rice and conventional rice. J. Food Sci. Technol., 2016, 51, 1010.
[http://dx.doi.org/10.1111/ijfs.13060]
[7]
Zuo, Y.; Yang, S.G.; Luo, Y.P.; Tan, Y.; Hao, G.F.; Wu, Q.Y.; Xi, Z.; Yang, G.F. Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors. Bioorg. Med. Chem., 2013, 21(11), 3245-3255.
[http://dx.doi.org/10.1016/j.bmc.2013.03.056] [PMID: 23623257]
[8]
Jiang, L.L.; Zuo, Y.; Wang, Z.F.; Tan, Y.; Wu, Q.Y.; Xi, Z.; Yang, G.F. Design and syntheses of novel N-(benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and N-(benzothiazol-5-yl)isoindoline-1,3-dione as potent protoporphyrinogen oxidase inhibitors. J. Agric. Food Chem., 2011, 59(11), 6172-6179.
[http://dx.doi.org/10.1021/jf200616y] [PMID: 21517076]
[9]
Huang, G.; Yang, J.C.; Li, H.C.; Zhang, J.; Liu, C.L. Design, synthesis and herbicidal activity ofnovel PPO inhibitors containing benzothiazole moiety. Pesticide, 2011, 50, 79.
[10]
Chen, S.; He, D. M.; Dong, X.; Cui, J. G.; Gan, C. F.; Huang, Y. M. Research Advance of Thiazole Compounds grochem, 2017, 1-8.
[11]
Liu, C.L.; Chai, B.S. New Agrochemicals Discovery and Synthesis; Beijing, 2013.
[12]
Carter, N.B.; Elliott, A.C.; Mccormack, D. HERBICIDAL PYRIDINO-/PYRIMIDINO-THIAZOLES. 2016. WO Patent 2016046078 A1.
[13]
Tony, T.; Ricky, H.; Negar, G.; Maurice, Y.; Ann, B. Process for the preparation of thiazole derivatives., 2015. E.P. Patent 2604268 B1.
[14]
Zhong, L.K.; Ni, Y.; Kong, X.Y.; Huang, H.Y.; Li, J.; Tang, W.; Zhang, R.R.; Kong, X.L.; Ji, W.J.; Xu, T.M. Synthesis and bioactivities of sulfinic esters containingsubstituted isoxazolyl moieties. Chin. J. Pestic. Sci., 2015, 17, 512.

Rights & Permissions Print Cite
Article Metrics
24
© 2024 Bentham Science Publishers | Privacy Policy