Design, Herbicidal Activity, and QSAR Analysis of Cycloalka[<i>d</i>]quinazoline-2,4-dione–Benzoxazinones as Protoporphyrinogen IX Oxidase Inhibitors

Wang, Dawei; Zhang, Ruibo; Ismail, Ismail; Xue, Zhi-Yuan; Liang, Lu; Yu, Shuyi; Wen, Xin; Xi, Zhen

doi:10.1021/acs.jafc.9b02996

Cited by 35 publications

(53 citation statements)

References 39 publications

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“…The herbicidal activity of synthetic compounds was evaluated according to a reported procedure 31 . Clopyralid was used as the reference control and the results represent the bioactivity triplicate.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Yang

Yin

et al. 2021

Pest Management Science

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BACKGROUND Picolinate/picolinic acid compounds are an important class of synthetic auxin herbicides. To explore the herbicidal activity of 6‐pyrazolyl picolinate compounds, a series of 3‐chloro‐6‐pyrazolyl‐picolinate derivatives was designed and synthesized. RESULTS Twenty‐five 3‐chloro‐6‐pyrazolyl‐picolinate derivatives synthesized were tested for herbicidal activity and the IC50 value of compound c5 to the growth of Arabidopsis thaliana root was 27 times lower than that of the commercial herbicide clopyralid. Compound c5 displayed better post‐emergence herbicidal activity and broader (Picloram, Clopyralid, Aminopyralid) herbicidal spectrum at a dosage of 400 g ha−1 in comparison with clopyralid; it also was safe to wheat and maize at this dosage. Arabidopsis thaliana phenotypes and expression of auxin‐response genes demonstrated that compound c5 might be a novel auxin‐type herbicide. Molecular docking analyses revealed that compound c5 had stronger binding ability to receptor AFB5 (auxin signaling F‐box protein 5) than clopyralid. CONCLUSION These 6‐pyrazolyl picolinate compounds could be used as potential lead structures for the discovery of a novel synthetic auxin herbicide. © 2021 Society of Chemical Industry

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Section: Methodsmentioning

confidence: 99%

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Yang

Yin

et al. 2021

Pest Management Science

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“…To determine the half maximal inhibitory concentration (IC 50 ) values of the four HPPD inhibitors (topramezone, mesotrione, tembotrione, and DKN) against Sp HPPD, various concentrations of each inhibitor were diluted with the 50 mM PBS buffer (pH 6.0) and preincubated with Sp HPPD at 35 °C for 30 min. The IC 50 values were calculated via nonlinear regression by fitting data to eq where y is the relative activity in the presence of inhibitor and x is the logarithm of inhibitor concentration. The K i value was calculated by fitting data to eq where K m is the Michaelis constant for 4-HPP, K m app is the apparent Michaelis constant for 4-HPP in the presence of an inhibitor, and [ I ] is the inhibitor concentration.…”

Section: Methodsmentioning

confidence: 99%

Isolation and Characterization of a Topramezone-Resistant 4-Hydroxyphenylpyruvate Dioxygenase from Sphingobium sp. TPM-19

Liu

Peng

Sheng

et al. 2019

J. Agric. Food Chem.

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Topramezone is a 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor. Due to its broad-spectrum, high efficiency, and low toxicity, topramezone is a candidate herbicide for the construction of genetically modified (GM) herbicide-resistant crops. In the present study, we screened a topramezone-resistant isolate Sphingobium sp. TPM-19 and cloned a topramezone-resistant HPPD gene (SphppD) from this isolate. SpHPPD shared the highest similarity (53%) with an HPPD from Vibrio vulnificus CMCP6. SpHPPD was synthesized in Escherichia coli BL21(DE3) and purified to homogeneity using Co2+-affinity chromatography. SpHPPD was found to be a monomer. The K m and k cat of SpHPPD for 4-hydroxyphenylpyruvate (4-HPP) were 82.8 μM and 15.0 s–1, respectively. SpHPPD showed high resistance to topramezone with half maximal inhibitory concentration (IC50) and K i values of 5.2 and 2.5 μM, respectively. Additionally, SpHPPD also showed high resistance to isoxaflutole (DKN) (IC50: 8.7 μM; K i: 6.0 μM) and mesotrione (IC50: 4.2 μM; K i: 1.3 μM) and moderate resistance to tembotrione (IC50: 2.5 μM; K i: 1.0 μM). The introduction of the SphppD gene into Arabidopsis thaliana enhanced obvious resistance against topramezone. In conclusion, this study provides a novel topramezone-resistant HPPD gene for the genetic engineering of GM herbicide-resistant crops.

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“…The effects of herbicides on crop safety is also important when it comes to herbicide development 67,68 . The impact of compound IV‐6 and oxyfluorfen on crop safety was evaluated using five common crops: soybean, cotton, corn, wheat, and rice.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

Zhao

Wang

Peng

et al. 2021

Pest Management Science

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BACKGROUND In recent years, protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors have been widely studied as important agricultural herbicides. Our research focused on the design and synthesis of novel PPO inhibitor herbicides, through linking of a diphenylether pyridine bioisostere structure to substituted coumarins, which aims to enhance environmental and crop safety while retaining high efficacy. RESULTS A total of 21 compounds were synthesized via acylation reactions and all compounds were characterized using infrared, 1H NMR, 13C NMR, and high‐resolution mass spectra. The respective configurations of compounds IV‐6 and IV‐12 were also confirmed using single crystal X‐ray diffraction. The bioassay results showed that the title compounds displayed notable herbicidal activity, particularly compound IV‐6 which displayed better herbicidal activity in greenhouse and field experiments, crop selectivity and safety for cotton and soybean compared with the commercial herbicide oxyfluorfen. CONCLUSION The work revealed that compound IV‐6 deserves further attention as a candidate structure for a novel and safe herbicide. © 2021 Society of Chemical Industry.

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Design, Herbicidal Activity, and QSAR Analysis of Cycloalka[d]quinazoline-2,4-dione–Benzoxazinones as Protoporphyrinogen IX Oxidase Inhibitors

Cited by 35 publications

References 39 publications

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Isolation and Characterization of a Topramezone-Resistant 4-Hydroxyphenylpyruvate Dioxygenase from Sphingobium sp. TPM-19

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

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