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

Zhao, Li‐Xia; Wang, Zhixin; Peng, Juan; Zou, Yue-Li; Hui, Yong-Zhuo; Chen, Yong‐Zheng; Gao, Shuang; Fu, Ying; Ye, Fei

doi:10.1002/ps.6523

Cited by 18 publications

(8 citation statements)

References 67 publications

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“…This provides a novel structural skeleton for the study of this class of compounds. Compound 15 , which was reported by Kalhor et al [ 37 ], showed fair to good activity, in which the 1,2,4 triazole structure contributed to the improvement of herbicidal activity and crop selectivity.…”

Section: Herbicides Containing Phenoxypyridine Scaffoldmentioning

confidence: 87%

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Liu

Yong

et al. 2022

Molecules

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Phenoxypyridine, the bioisostere of diaryl ethers, has been widely introduced into bioactive molecules as an active scaffold, which has different properties from diaryl ethers. In this paper, the bioactivities, structure-activity relationships, and mechanism of compounds containing phenoxypyridine were summarized, which may help to explore the lead compounds and discover novel pesticides with potential bioactivities.

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Section: Herbicides Containing Phenoxypyridine Scaffoldmentioning

confidence: 87%

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Liu

Yong

et al. 2022

Molecules

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“…Moreover, compared with compound IV-6 and compound 9d, we previously reported excellent activity. 21,64 The inhibitory activity of compound G4 against PPO was comparable to that of compound IV-6 and higher than that of compound 9d. Therefore, the SAR of phenoxypyridine derivatives containing five-membered heterocycles was discussed in detail as follows.…”

Section: A B a = −mentioning

confidence: 90%

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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“…Structure-activity relationship (SAR) studies allow us to reveal approaches to the synthesis of equivalents and simplified analogs of NPs, as well as so-called pseudo-natural compounds [ 217 , 218 , 219 ]. Recently, a large number of SAR studies have appeared on the semi-synthetic derivatives of plant metabolites as potential CHs, for example, with maslinic acid [ 220 ], 2,4,5-trimethoxybenzaldehyde [ 221 ], coumarin [ 222 ], and berberine [ 223 ]. However, there are still relatively few papers on the SAR of microbial phytotoxins.…”

Section: Natural Phytotoxins As Prototypes Of Synthetic Herbicidesmentioning

confidence: 99%

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Berestetskiy

2023

Plants

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Weeds are a permanent component of anthropogenic ecosystems. They require strict control to avoid the accumulation of their long-lasting seeds in the soil. With high crop infestation, many elements of crop production technologies (fertilization, productive varieties, growth stimulators, etc.) turn out to be practically meaningless due to high yield losses. Intensive use of chemical herbicides (CHs) has led to undesirable consequences: contamination of soil and wastewater, accumulation of their residues in the crop, and the emergence of CH-resistant populations of weeds. In this regard, the development of environmentally friendly CHs with new mechanisms of action is relevant. The natural phytotoxins of plant or microbial origin may be explored directly in herbicidal formulations (biorational CHs) or indirectly as scaffolds for nature-derived CHs. This review considers (1) the main current trends in the development of CHs that may be important for the enhancement of biorational herbicides; (2) the advances in the development and practical application of natural compounds for weed control; (3) the use of phytotoxins as prototypes of synthetic herbicides. Some modern approaches, such as computational methods of virtual screening and design of herbicidal molecules, development of modern formulations, and determination of molecular targets, are stressed as crucial to make the exploration of natural compounds more effective.

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

Cited by 18 publications

References 67 publications

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

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

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

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