Synthesis and herbicidal activities of novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives

Xu, Han; Xiao, Hu; Zhu, You‐Quan; Zou, Xiao‐Mao; Liu, Bin; Hu, Fang‐Zhong; Yang, Hai‐Tao

doi:10.1007/s11426-010-0014-2

Cited by 11 publications

(5 citation statements)

References 22 publications

(34 reference statements)

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“…Growth Inhibition of Barnyard Grass (Echinochloa crus-galli (L.) Beauv.). 42 The compounds to be evaluated were made into emulsions to aid dissolution. Five milliliters of inhibitor solution was added to a 50 mL cup covered with a layer of glass beads and a piece of filter paper at the bottom, where ten seeds of E. crus-galli were placed.…”

Section: -((4-methylbenzyl)thio)-4-(3-(trifluoromethyl)phenyl)-4h-124...mentioning

confidence: 99%

“…Root Inhibition of Rape (Brassica napus). 42 The compounds to be tested were made into emulsions to aid dissolution. 2.5 mL of inhibitor solution was added to a filter paper in a 5.6 cm Petri plate, where 10 rape seeds were placed after soaking in distilled water for 4 h. The plate was placed in a dark room and allowed to germinate for 72 h at 28 °C.…”

Section: -((5-(hydroxymethyl)-4-(3-(trifluoromethyl)phenyl)-4h-124tri...mentioning

confidence: 99%

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Discovery of (5-(Benzylthio)-4-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl) Methanols as Potent Phytoene Desaturase Inhibitors through Virtual Screening and Structure Optimization

Zhang

Zhou

Yang

et al. 2022

J. Agric. Food Chem.

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Phytoene desaturase (PDS) is not only an important enzyme in the biosynthesis of carotenoids but also a promising target for herbicide discovery. However, in recent years, no expected PDS inhibitors with new scaffolds have been reported. Hence, a solution for developing PDS inhibitors is to search for new compounds with novel chemotypes based on the PDS protein structure. In this work, we integrated structure-based virtual screening, structure-guided optimization, and biological evaluation to discover some PDS inhibitors with novel chemotypes. It is noteworthy that the highly potent compound 1b, 1-(4-chlorophenyl)-2-((5-(hydroxymethyl)-4-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)thio)ethan-1-one, exhibited a broader spectrum of post-emergence herbicidal activity at 375–750 g/ha against six kinds of weeds than the commercial PDS inhibitor diflufenican. Surface plasmon resonance (SPR) assay showed that the affinity of our compound 1b (K D = 65.9 μM) to PDS is slightly weaker but at the same level as diflufenican (K D = 38.3 μM). Meanwhile, determination of the phytoene content and PDS mRNA quantification suggested that 1b could induce PDS mRNA reduction and phytoene accumulation. Moreover, 1b also caused the increase of reactive oxygen species (ROS) and the change of ROS-associated enzyme activity in albino leaves. Hence, all these results indicated the feasibility of PDS protein structure-based virtual screen and structure optimization to search for highly potent PDS inhibitors with novel chemotypes for weed control.

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Section: -((4-methylbenzyl)thio)-4-(3-(trifluoromethyl)phenyl)-4h-124...mentioning

confidence: 99%

Section: -((5-(hydroxymethyl)-4-(3-(trifluoromethyl)phenyl)-4h-124tri...mentioning

confidence: 99%

Discovery of (5-(Benzylthio)-4-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl) Methanols as Potent Phytoene Desaturase Inhibitors through Virtual Screening and Structure Optimization

Zhang

Zhou

Yang

et al. 2022

J. Agric. Food Chem.

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“…The synthetic routes for the intermediates 7-12 were the same as for our previous reports [13,17,20]. The details are shown in the Supporting Information.…”

Section: Preparation Of the Intermediates 7-12mentioning

confidence: 99%

In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors

Yang

Wang

et al. 2021

Molecules

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A series of novel 3-phenoxy-4-(3-trifluoromethylphenyl)pyridazines 2–5 were designed, based on the structure of our previous lead compound 1 through the in silico structure-guided optimization approach. The results showed that some of these new compounds showed a good herbicidal activity at the rate of 750 g ai/ha by both pre- and post-emergence applications, especially compound 2a, which displayed a comparable pre-emergence herbicidal activity to diflufenican at 300–750 g ai/ha, and a higher post-emergence herbicidal activity than diflufenican at the rates of 300–750 g ai/ha. Additionally, 2a was safe to wheat by both pre- and post-emergence applications at 300 g ai/ha, showing the compound’s potential for weed control in wheat fields. Our molecular simulation studies revealed the important factors involved in the interaction between 2a and Synechococcus PDS. This work provided a lead compound for weed control in wheat fields.

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“…They were explained as anti-inflammatory drugs including, Emorfazone and related compounds, for therapeutic intervention of renal-urologic (FK838), cardiovascular (EMD57283), respiratory (NIP502), dermatologic diseases (FR- [12], and antihypertensive [13] activities. They possess antimicrobial [14], anti-inflammatory [15,16], anti feedant [17], herbicidal [18], and anti nocieceptiv [19] activities, as well. Some pyridazinones are well known as potent analgesics, antiplatelet [20,21] and anticancer agents [22] antidepressant, antithrombotic, diureti, anti-HIV makes curious interest towards the construction of new pyridazinone compounds as well as other anticipated biological and pharmacological properties [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

A Review on Pyridazinone Ring Containing Various Cardioactive Agents

Asif

2019

J. Chem. Rev.

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In this work, some pyridazinones were studied for their cardioactive activity. These compounds showed significant cardio-active action with respect to the regular used drugs. However, it was found that the existence of the pyridazine ring is a crucial necessity in the structure of these pyridazinonecompounds to show the improved cardioactive activities. It was also understood that the substitution of the different group on the pyridazinone ring with other related bioisosteres or isosteres along with the existence of pyridazine ring may provide better cardioactive compounds. Pyridazinoneis, a component of various cardio-active agents, which are in uses clinically or in clinical trials. These contain pimobendan, indolidan, levosimendan, imazodan, CI-930, meribendan, bemoradan, senazodan, siguazodan, amipizone, prinoxodan, Y-590, SK&F-93741, SKF 95654, NSP-805, NSP-804 and KF 15232. This study briefly reviews the pyridazinone ring for the progress of new cardio-active drugs.

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Synthesis and herbicidal activities of novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives

Cited by 11 publications

References 22 publications

Discovery of (5-(Benzylthio)-4-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl) Methanols as Potent Phytoene Desaturase Inhibitors through Virtual Screening and Structure Optimization

Discovery of (5-(Benzylthio)-4-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl) Methanols as Potent Phytoene Desaturase Inhibitors through Virtual Screening and Structure Optimization

In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors

A Review on Pyridazinone Ring Containing Various Cardioactive Agents

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