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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.

A series of novel triazone derivatives containing acylhydrazone and phenoxypyridine motifs were designed, synthesized, and evaluated for their biological activities. The bioassay results indicated that most of the target compounds exhibited excellent insecticidal activities against bean aphids. In particular, compounds 3i and 3e showed excellent aphicidal activities comparable to pymetrozine, thus emerging as novel insecticidal lead compounds. Additionally, compounds 3c (60%), 3e (60%), and 3f (60%) exhibited good larvicidal activities against C. pipiens pallens at 0.5 mg/kg. Further fungicidal activity tests revealed that most derivatives exhibited broad-spectrum fungicidal activities. A total of twelve compounds exhibited better fungicidal activities against cercospora arachidicola hori than carbendazim, and eight compounds exhibited better fungicidal activities against fusarium moniliforme than carbendazim. This work suggests that compound 3e could serve as an insecticidal lead compound for further structural optimization.

In this paper, a series of phenoxypyridine-containing chalcone derivatives ( L1 – L28 ) were designed and synthesized, characterized on NMR and HRMS. Ningnanmycin (NNM) was used as a control agent. The results of the antiviral activity testing showed that the curative activity EC 50 values of L1 and L4 against TMV were 140.5 and 90.7 μg/mL, respectively, which were superior to that of NNM (148.3 μg/mL). The EC 50 values of 154.1, 102.6 and 140.0 μg/mL for the anti-TMV protective activities of L1 , L4 and L15 were superior to that of NNM (188.2 μg/mL). The mechanism of action between L4 and NNM and tobacco mosaic virus capsid protein (TMV-CP) was preliminarily investigated. The results of microscale thermophoresis (MST) experiments showed that L4 had a strong binding affinity for TMV-CP with a dissociation constant Kd value of 0.00149 µM, which was better than that of NNM (2.73016 µM). The results of molecular docking experiments showed that L4 formed shorter hydrogen bonds with amino acid residues of TMV-CP than NNM and formed more amino acid residues than NNM, which indicated that L4 was more tightly bound to TMV-CP. This study suggested that phenoxypyridine-containing chalcone derivatives can be used as new anti-TMV drugs through further research and development. Graphical abstract

The herbicide fomesafen has the advantages of low toxicity and high selectivity, and the target of this compound is protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4). However, this herbicide has a long residual period and can have phytotoxic effects on succeeding crops. To protect maize from fomesafen, a series of thiazole phenoxypyridines were designed based on structure–activity relationships, active substructure combinations, and bioisosterism. Bioassays showed that thiazole phenoxypyridines could improve maize tolerance under fomesafen toxicity stress to varying degrees at a dose of 10 mg·kg−1. Compound 4i exhibited the best effects. After being treated by compound 4i, average recovery rates of growth index exceeded 72%, glutathione content markedly increased by 167% and glutathione S-transferase activity was almost 163% of fomesafen-treated group. More importantly, after being treated by compound 4i, the activity of PPO, the main target enzyme of fomesafen, recovered to 93% of the control level. The molecular docking result exhibited that the compound 4i could compete with fomesafen to bind with the herbicide target enzyme, which consequently attained the herbicide detoxification. The present work suggests that compound 4i could be developed as a potential safener to protect maize from fomesafen.