Hostname: page-component-78c5997874-94fs2 Total loading time: 0 Render date: 2024-11-12T04:39:04.221Z Has data issue: false hasContentIssue false
  • English
  • Français

Herbicidal activity and molecular docking study of novel PPO inhibitors

Published online by Cambridge University Press:  28 August 2020

Li-Xia Zhao ,
Mao-Jun Jiang ,
Jia-Jun Hu ,
Yue-Li Zou ,
Shuang Gao ,
Ying Fu  and
Fei Ye
Li-Xia Zhao
Affiliation:
Associate Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Mao-Jun Jiang
Affiliation:
Master’s Degree Student, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Jia-Jun Hu
Affiliation:
Master’s Degree Student, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Yue-Li Zou
Affiliation:
Senior Experimentalist, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Shuang Gao
Affiliation:
Associate Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Ying Fu*
Affiliation:
Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Fei Ye*
Affiliation:
Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
*
Authors for correspondence: Ying Fu, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin150030, China. (Email: fuying@neau.edu.cn); and Fei Ye, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin150030, China. (Email: yefei@neau.edu.cn)
Authors for correspondence: Ying Fu, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin150030, China. (Email: fuying@neau.edu.cn); and Fei Ye, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin150030, China. (Email: yefei@neau.edu.cn)
Get access Rights & Permissions [Opens in a new window]

Abstract

Protoporphyrinogen oxidase (PPO) is an important target for discovering new herbicides that interfere with the synthesis of porphyrin. To discover new PPO inhibitors with improved biological activity, a series of new diphenyl ethers containing tetrahydrophthalimide were designed and synthesized. Among them, J6.1 (IC50 = 4.7 nM) and J6.3 (IC50 = 30.0 nM) show higher maize (Zea mays L.) PPO inhibitory activity than the commercial herbicides oxyfluorfen (IC50 = 117.9 nM) and flumioxazin (IC50 = 157.1 nM). The greenhouse herbicidal activity of J6.3 is comparable to that of oxyfluorfen, and it is greater than that of flumioxazin. Even at a dose of 300 g ai ha−1, cotton (Gossypium hirsutum L.) and peanut (Arachis hypogaea L.) show greater tolerance to J6.3, suggesting that J6.3 could be used for further development of new herbicide candidates in those fields. In addition, molecular docking has been used to further study the mechanism of action of J6.3. The results show that the introduction of a nitro group and tetrahydrophthalimide into the diphenyl ether structure is beneficial to biological activity.

Keywords

Biological activitydiphenyl ethertetrahydrophthalimide
Type
Research Article
Information
Weed Science , Volume 68 , Issue 6 , November 2020 , pp. 565 - 574
Copyright
© The Author(s), 2020. Published by Cambridge University Press on behalf of the Weed Science Society of America

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Footnotes

Associate Editor: Dean Riechers, University of Illinois

*

These authors contributed equally to this work.

References

Alcantara-de la Cruz, R, Dominguez-Martinez, PA, Silveira, HM, Cruz-Hipolito, HE, Palma-Bautista, C, Vazquez-Garcia, JG, Dominguez-Valenzuela, JA, De Prado, R (2019) Management of glyphosate-resistant weeds in Mexican citrus groves: chemical alternatives and economic viability. Plants 8:325 10.3390/plants8090325CrossRefGoogle ScholarPubMed
Begunov, RS, Valyaeva, AN, Belyaev, VV, Dobretsova, NO (2015) Ultrasound synthesis of diaryl ethers. Russ Chem Bull 64:1971–1974 CrossRefGoogle Scholar
Cui, M, Chen, Z, Liu, T, Wang, H, Zeng, Z (2017) N-acylsuccinimides: efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via CN cleavage. Tetrahedron Lett 58:3819–3822 10.1016/j.tetlet.2017.08.044CrossRefGoogle Scholar
Dayan, FE, Barker, A, Tranel, PJ (2018) Origins and structure of chloroplastic and mitochondrial plant protoporphyrinogen oxidases: implications for the evolution of herbicide resistance. Pest Manag Sci 74:2226–2234 10.1002/ps.4744CrossRefGoogle ScholarPubMed
Dayan, FE, Dayan, EA (2011) Porphyrins: one ring in the colors of life a class of pigment molecules binds King George III, vampires and herbicides. Am Sci 99:236–243 10.1511/2011.90.236CrossRefGoogle Scholar
Duke, SO, Lydon, J, Becerril, JM, Sherman, TD, Lehnen, LP, Matsumoto, H (1991) Protoporphyrinogen oxidase-inhibiting herbicides. Weed Sci 39:465–473 10.1017/S0043174500073239CrossRefGoogle Scholar
Fu, Y, Zhang, SQ, Liu, YX, Wang, JY, Gao, S, Zhao, LX, Ye, F (2019a) Design, synthesis, SAR and molecular docking of novel green niacin-triketone HPPD inhibitor. Ind Crop Prod 137:566–575 10.1016/j.indcrop.2019.05.070CrossRefGoogle Scholar
Fu, Y, Zhang, D, Zhang, S, Liu, Y, Guo, Y, Wang, M, Gao, S, Zhao, L-X, Ye, F (2019b) Discovery of N-aroyl diketone/triketone derivatives as novel 4-hydroxyphenylpyruvatedioxygenase inhibiting-based herbicides. J Agric Food Chem 67:11839–11847 10.1021/acs.jafc.9b01412CrossRefGoogle Scholar
Gao, S, Liu, YY, Jiang, JY, Li, XM, Zhao, LX, Fu, Y and Ye, F (2020) Encapsulation of thiabendazole in hydroxypropyl-β-cyclodextrin nanofibers via polymer-free electrospinning and its characterization. Pest Manag Sci, 10.1002/ps.5885 10.1002/ps.5885CrossRefGoogle ScholarPubMed
Heap, I, Duke, SO (2018) Overview of glyphosate-resistant weeds worldwide. Pest Manag Sci 74:1040–1049 10.1002/ps.4760CrossRefGoogle ScholarPubMed
Hossian, A, Jana, R (2016) Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement. Org Biomol Chem 14:9768–9779 10.1039/C6OB01758DCrossRefGoogle ScholarPubMed
Jiang, LL, Zuo, Y, Wang, ZF, Tan, Y, Wu, QY, Xi, Z, Yang, GF (2011) 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 59:6172–6179 10.1021/jf200616yCrossRefGoogle Scholar
Jones, JW, Price, TL, Huang, FH, Zakharov, L, Rheingold, AL, Slebodnick, C, Gibson, HW (2018) Pseudocryptand hosts for paraquats and diquats. J Org Chem 83:823–834 10.1021/acs.joc.7b02812CrossRefGoogle ScholarPubMed
Kaur, S, Sandell, LD, Lindquist, JL, Jhala, AJ (2014) Glyphosate-resistant giant ragweed (Ambrosia trifida) control in glufosinate-resistant soybean. Weed Technol 28:569–577 10.1614/WT-D-14-00009.1CrossRefGoogle Scholar
Li, AJ, Zhang, HX (2013) Synthesis of diflufenican. Agrochem 52:565–567 Google Scholar
Li, HB, Li, YH, Liu, B, Wang, YF, Wu, C, Zou, XM, Yang, HZ (2007) Study of method for measuring the inhibition of protoporphyrinogen oxidase activity in vitro. J Plant Physiol 43:1152–1156 Google Scholar
Matsuo, M, Taniguchi, K, Katsura, Y, Kamitani, T, Ueda, I (1985) New 2-aryliminoimidazolidines. 1. Synthesis and antihypertensive properties of 2-(2-phenoxyphenylimino)imidazolidines and related-compounds. Chem Pharm Bull 33:4409–4421 10.1248/cpb.33.4409CrossRefGoogle Scholar
Meng, GR, Szostak, M (2016) Rhodium-catalyzed C-H bond functionalization with amides by double C-H/C-N bond activation. Org Lett 18:796–799 10.1021/acs.orglett.6b00058CrossRefGoogle ScholarPubMed
Powles, SB (2008) Evolved glyphosate-resistant weeds around the world: lessons to be learnt. Pest Manag Sci 64:360–365 10.1002/ps.1525CrossRefGoogle ScholarPubMed
Qin, XH, Sun, L, Wen, X, Yang, X, Tan, Y, Jin, H, Cao, QY, Zhou, WH, Xi, Z, Shen, YQ (2010) Structural insight into unique properties of protoporphyrinogen oxidase from Bacillus subtilis . J Struct Biol 170:76–82 10.1016/j.jsb.2009.11.012CrossRefGoogle ScholarPubMed
Schryver, MG, Soltani, N, Hooker, DC, Robinson, DE, Tranel, PJ, Sikkema, PH (2017) Control of glyphosate-resistant common waterhemp (Amaranthus rudis) in three new herbicide-resistant soybean varieties in ontario. Weed Technol 31:828–837 10.1017/wet.2017.81CrossRefGoogle Scholar
Shibata, A, Kodaka, R, Fujisawa, T, Katagi, T (2011) Degradation of flumioxazin in illuminated water-sediment systems. J Agric Food Chem 59:11186–11195 10.1021/jf202542vCrossRefGoogle ScholarPubMed
Ucles, S, Hakme, E, Ferrer, C, Fernandez-Alba, AR (2018) Analysis of thermally labile pesticides by on-column injection gas chromatography in fruit and vegetables. Anal Bioanal Chem 410:6861–6871 10.1007/s00216-018-1286-1CrossRefGoogle ScholarPubMed
Urai, Á, Váradi, A, Szőcs, L, Komjáti, B, Le Rouzic, V, Hunkele, A, Pasternak, GW, Majumdar, S, Hosztafi, S (2017) Synthesis and pharmacological evaluation of novel selective MOR agonist 6β-pyridinyl amidomorphines exhibiting long-lasting antinociception. Med Chem Commun 8:152–157 10.1039/C6MD00450DCrossRefGoogle ScholarPubMed
Wang, BF, Wen, X, Qin, XH, Wang, ZF, Tan, Y, Shen, YQ, Xi, Z (2013) Quantitative structural insight into human variegate porphyria disease. J Biol Chem 288:11731–11740 10.1074/jbc.M113.459768CrossRefGoogle ScholarPubMed
Wang, DW, Li, Q, Wen, K, Ismail, I, Liu, DD, Niu, CW, Wen, X, Yang, GF, Xi, Z (2017) Synthesis and herbicidal activity of pyrido 2,3-d pyrimidine-2,4-dione-benzoxazinone hybrids as protoporphyrinogen oxidase inhibitors. J Agric Food Chem 65:5278–5286 10.1021/acs.jafc.7b01990CrossRefGoogle ScholarPubMed
Wang, DW, Zhang, RB, Yu, SY, Liang, L, Ismail, I, Li, YH, Xu, H, Wen, X, Xi, Z (2019) Discovery of novel N-isoxazolinylphenyltriazinones as promising protoporphyrinogen IX oxidase inhibitors. J Agric Food Chem 67:12382–12392 10.1021/acs.jafc.9b04844CrossRefGoogle ScholarPubMed
Wang, MJ, Nan, X, Feng, G, Yu, HT, Hu, GF, Liu, YQ (2014) Design, synthesis and bioactivity evaluation of novel acylthiourea derivatives of cantharidin. Ind Crop Prod 55:11–18 10.1016/j.indcrop.2014.02.007CrossRefGoogle Scholar
Yang, R (2001) Advances on development of tetrahydrophthalimide herbicides. Pesticides 41:7–9 Google Scholar
Ye, F, Ma, P, Zhang, YY, Li, P, Yang, F, Fu, Y (2018) Herbicidal activity and molecular docking study of novel accase inhibitors. Front Plant Sci 9:10 10.3389/fpls.2018.01850CrossRefGoogle ScholarPubMed
Ye, F, Zhai, Y, Guo, KL, Liu, YX, Li, N, Gao, S, Zhao, LX, Fu, Y (2019a) Safeners improve maize tolerance under herbicide toxicity stress by increasing the activity of enzymes in vivo. J Agric Food Chem 67:11568–11576 CrossRefGoogle ScholarPubMed
Ye, F, Zhai, Y, Kang, T, Wu, SL, Li, JJ, Gao, S, Zhao, LX, Fu, Y (2019b) Rational design, synthesis and structure-activity relationship of novel substituted oxazole isoxazole carboxamides as herbicide safener. Pest Biochem Physiol 157:60–68 CrossRefGoogle ScholarPubMed
Yu, HB, Yang, HB, Gui, DL, Lv, L, Li, B (2011) Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates. J Agric Food Chem 59:11718–11726 10.1021/jf2039444CrossRefGoogle ScholarPubMed
Zhang, YY, Gao, S, Hoang, MT, Wang, ZW, Ma, X, Zhai, Y, Zhao, LX, Fu, Y, Ye, F (2020a) Protective efficacy of novel phenoxyacetyl oxazolidine derivatives as safeners against nicosulfuron toxicity in maize. Pest Manag Sci, 10.1002/ps.6005 CrossRefGoogle Scholar
Zhang, YY, Gao, S, Liu, YX, Wang, C, Jiang, W, Zhao, LX, Fu, Y, Ye, F (2020b) Design, synthesis, and biological activity of novel diazabicyclo derivatives as safeners. J Agric Food Chem 68:3403–3414 10.1021/acs.jafc.9b07449CrossRefGoogle ScholarPubMed
Zhao, LX, Jiang, MJ, Hu, JJ, Zou, Y-L, Cheng, Y, Ren, T, Gao, S, Fu, Y, Ye, F (2020) Design, synthesis, and herbicidal activity of novel diphenyl ether derivatives containing fast degrading tetrahydrophthalimide. J Agric Food Chem 68:3729–3741 CrossRefGoogle ScholarPubMed
Supplementary material: File

Zhao et al. Supplementary Materials

Zhao et al. Supplementary Materials

Download Zhao et al. Supplementary Materials(File)
File 59.9 MB