Synthesis, In Vitro Protoporphyrinogen Oxidase Inhibition, and Herbicidal Activity of N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindole‐1,3‐diones and N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindol‐1‐ones

Wu, Qiong‐You; Jiang, Lili; Zuo, Yang; Wang, Zhifang; Xi, Zhen; Yang, Guang‐Fu

doi:10.1111/cbdd.12331

Cited by 15 publications

(8 citation statements)

References 37 publications

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“…Two notable examples of this ring-closure strategy are commercial herbicides flumioxazin and thiadiazimin, in which benzooxazin-3-one was introduced by assembling the substituent at the C-4′ and C-6′ into a six-membered oxazinone ring. Benzothiazole, an important heterocycle with a wide range of biological activities including anticancer, antiviral, antimicrobial, and antifungal activity, − has been widely applied in agrochemistry. , Previously, we successfully integrated the benzothiazole moiety with diverse heterocycles to develop novel agrochemicals with high-potential fungicidal or herbicidal activities. ,,− It was revealed that the incorporation of benzothiazole with heterocycles such as triazolinone or tetrahydro-2 H -isoindole-1,3-dione could result in both an enhancement in herbicidal potency and improvement of the crop selectivity. Inspired by these findings, herein, we report the design and synthesis of a series of novel PPO inhibitors, 1-methyl-3-phenyl-6-(trifluoromethyl)pyrimidine-2,4-dione, by incorporating benzothiazole moiety with a pyrimidine-2,4-dione component (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Zuo

et al. 2016

J. Agric. Food Chem.

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Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is known as a key action target for several structurally diverse herbicides. As a continuation of our research work on the development of new PPO-inhibiting herbicides, a series of novel 3-(2'-halo-5'-substituted-benzothiazol-1'-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-diones 9 were designed and synthesized. The bioassay results indicated that a number of the newly synthesized compounds exhibited higher inhibition activity against tobacco PPO (mtPPO) than the controls, saflufenacil and sulfentrazone. Compound 9F-5 was identified as the most potent inhibitor with a Ki value of 0.0072 μM against mtPPO, showing about 4.2-fold and 1.4-fold higher potency than sulfentrazone (Ki = 0.03 μM) and saflufenacil (Ki = 0.01 μM), respectively. An additional green house assay demonstrated that compound 9F-6 (Ki = 0.012 μM) displayed the most promising postemergence herbicidal activity with a broad spectrum even at a concentration as low as 37.5 g of active ingredient (ai)/ha. Maize exhibits relative tolerance against compound 9F-6 at the dosage of 150 g ai/ha, but it is susceptible to saflufenacil even at 75 g ai/ha. Thus, compound 9F-6 exhibits the potential to be a new herbicide for weed control in maize fields.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Zuo

et al. 2016

J. Agric. Food Chem.

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“…and 0°C for 6 min. Assays were performed in 96‐well plates at 30°C using an ultraviolet–visible spectrophotometer to monitor the concentration of protoporphyrin IX at 410 nm 43,44 . The inhibitory rate of the title compounds on the enzyme was calculated using Equation ():

I = \frac{(a - b)}{a}

where I is the inhibition rate, a is the catalytic rate of the enzyme when no inhibitor is added, b is the catalytic rate of the enzyme when target compounds or commercial herbicide are added.…”

Section: Methodsmentioning

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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“…To date, 13 weeds have been identified as resistant to PPOinhibiting herbicides. 18 Therefore, the development of novel PPO inhibitors has become a key scientific research direction in the global pesticide field.…”

Section: ■ Introductionmentioning

confidence: 99%

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

Zhao

Peng

Liu

et al. 2022

J. Agric. Food Chem.

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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.

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Synthesis, In Vitro Protoporphyrinogen Oxidase Inhibition, and Herbicidal Activity of N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindole‐1,3‐diones and N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindol‐1‐ones

Cited by 15 publications

References 37 publications

Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

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

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

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