Quinoxaline derivatives as herbicide safeners by improving Zea mays tolerance

Self Cite

Cinnamic acid, isolated from cinnamon bark, is a natural product with excellent bioactivity, and it effectively binds with cyclohexanedione to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors. According to the active sub-structure combination principle, a series of novel 3-hydroxy-2-cinnamoyl-2-en-1-one derivatives were designed and synthesized. The title compounds were characterized by infrared, 1H NMR, 13C NMR, and HRMS. The in vitro inhibitory activity of AtHPPD verified that compound II-13 showed the most activity with a half-maximal inhibitory concentration (IC50) value of 0.180 μM, which was superior to that of mesotrione (0.206 μM) in vitro. The preliminary herbicidal activity tests demonstrated that some compounds had good herbicidal activity especially compound II-13 at a concentration of 150 g ai/ha. The binding mode of AtHPPD through molecular docking indicated that two oxygens of compounds II-13 formed bidentate interactions with metal ions, and the benzene ring formed π-π accumulation effects with Phe-381 and Phe-424. The results of molecular dynamics simulations showed that compound II-13 exhibited a more stable binding ability with AtHPPD than mesotrione. This study provided insights into the development of natural and efficient herbicides in the future.

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Structure–Activity Relationship, Molecular Docking, and Herbicidal Evaluation of 2-Cinnamoyl-3-Hydroxycyclohex-2-en-1-one Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Song

Zhao

Zhang

et al. 2021

Self Cite

“…37 In addition, substructure splicing is a common means for inventing new drugs. 38 Therefore, in this article, the pyridine ring is first used to replace one of the benzene rings in the diphenyl ether through bioisosterism design, and then the oxime ester and fivemembered heterocyclic ring are linked through substructure splicing. Thus, a series of novel diphenyl ether derivatives containing five-membered heterocycles were designed and synthesized (Figure 2).…”

Section: ■ Introductionmentioning

confidence: 99%

Design, Synthesis, and Herbicidal Activity of Diphenyl Ether Derivatives Containing a Five-Membered Heterocycle

Zhao

Peng

Liu

et al. 2022

Self Cite

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is an important target for discovering novel herbicides, and it causes bleaching symptoms by inhibiting the synthesis of chlorophyll and heme. In this study, the active fragments of several commercial herbicides were joined by substructure splicing and bioisosterism, and a series of novel diphenyl ether derivatives containing fivemembered heterocycles were synthesized. The greenhouse herbicidal activity and the PPO inhibitory activity in vitro were discussed in detail. The results showed that most compounds had good PPO inhibitory activity, and target compounds containing trifluoromethyl groups tended to have higher activity. Among them, compound G4 showed the best inhibitory activity, with a halfmaximal inhibitory concentration (IC 50 ) of 0.0468 μmol/L, which was approximately 3 times better than that of oxyfluorfen (IC 50 = 0.150 μmol/L). In addition, molecular docking indicated that compound G4 formed obvious π−π stacking interactions and hydrogen bond interactions with PHE-392 and ARG-98, respectively. Remarkably, compound G4 had good safety for corn, wheat, rice, and soybean, and the cumulative concentration in crops was lower than that of oxyfluorfen. Therefore, compound G4 can be used to develop potential lead compounds for novel PPO inhibitors.

“…Due to its excellent properties in photochemistry and photophysics, it is commonly used in construction of chemical sensors. , Inspired by these findings and our continuous interest in pesticide determination, a competitive coordination-based chemosensor, 2-(benzothiazol)-4-(3-hydroxy-4-methylphenyl)imino phenol ( BHMH ), was designed and synthesized through the Schiff base reaction (Scheme ). , Compared with the same type of fluorescent probes, the advantages of BHMH were its lower detection line, good water solubility, and biocompatibility. − The BHMH-Cu 2+ /Fe 3+ complex was employed to selectively and sensitively monitor glyphosate accompanied by a fluorescence “turn-on” mode. Glyphosate exhibited a stronger chelation with Cu 2+ /Fe 3+ than BHMH and the system released free BHMH through the competitive coordination in dimethyl sulfoxide/4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (DMSO/HEPES) (1:4, v/v, pH = 6.0).…”

Section: Introductionmentioning

confidence: 99%

“…23,24 Inspired by these findings and our continuous interest in pesticide determination, a competitive coordination-based chemosensor, 2-(benzothiazol)-4-(3-hydroxy-4-methylphenyl)imino phenol (BHMH), was designed and synthesized through the Schiff base reaction (Scheme 1). 25,26 Compared with the same type of fluorescent probes, the advantages of BHMH were its lower detection line, good water solubility, and biocompatibility. 27−29 The BHMH-Cu 2+ /Fe 3+ complex was employed to selectively and sensitively monitor glyphosate accompanied by a fluorescence "turn-on" mode.…”

Section: ■ Introductionmentioning

confidence: 99%

New Fluorescent Probes for the Sensitive Determination of Glyphosate in Food and Environmental Samples

Sun

Yang

et al. 2021

Self Cite

In this paper, a dual-functional probe, 2-(benzothiazol)-4-(3-hydroxy-4-methylphenyl) imino phenol (BHMH), was synthesized and characterized for the simultaneous detection of Cu2+ and Fe3+ in dimethyl sulfoxide/4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (DMSO/HEPES) (1:4, v/v, pH = 6.0). The limits of detections (LODs) for Cu2+ and Fe3+ were 9.05 and 48 nM, respectively. Based on the competitive coordination, the complex BHMH-Cu 2+ /Fe 3+ exhibited good sensitivity and selectivity for glyphosate. The LODs of BHMH-Cu 2+ and BHMH-Fe 3+ for glyphosate were 0.41 and 0.63 μM, respectively. The probe quantitatively detected glyphosate in tap water, Songhua River water, local water and soil, and food samples. The colorimetric on-site glyphosate sensing through the probe BHMH-Cu 2+ was also studied based on smartphones. BHMH and BHMH-Cu 2+ /Fe 3+ exhibited outstanding imaging capabilities for Cu2+, Fe3+, and glyphosate in living cells with low cytotoxicity, especially the first time for glyphosate.