作为除草剂安全剂的新型芳基取代甲酰基恶唑烷衍生物的设计、合成和构效关系,Journal of Agricultural and Food Chemistry

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作为除草剂安全剂的新型芳基取代甲酰基恶唑烷衍生物的设计、合成和构效关系
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-05-16 , DOI: 10.1021/acs.jafc.3c00467
Yu Ding ₁ , Dong-Mei Zhao ₂ , Tao Kang ₁ , Juan Shi ₁ , Fei Ye _{1,

2} , Ying Fu ₁

Affiliation

烟嘧磺隆是全球磺酰脲类（SU）除草剂市场领先的除草剂；它是由杜邦和石原共同开发的。近年来，烟嘧磺隆的广泛使用导致环境危害、对后茬作物的影响等农业生产危害日益突出。除草安全剂的使用可以显着减轻除草剂的药害，保护作物植株，扩大现有除草剂的应用范围。采用活性基团组合法设计了一系列新型芳基取代甲酰基恶唑烷衍生物。使用高效的一锅法合成标题化合物，并通过红外 (IR) 光谱法、¹ H 和^{13进行表征}C核磁共振（NMR）和高分辨率质谱（HRMS）。通过X射线单晶进一步鉴定了化合物V-25的化学结构。生物活性测定和构效关系证明烟嘧磺隆对玉米的植物毒性可以被大多数标题化合物降低。测定了体内谷胱甘肽S-转移酶 (GST) 活性和乙酰乳酸合酶 (ALS) ，化合物V-12显示出与商业安全剂异恶草醚相当的鼓舞人心的活性。分子对接模型表明化合物V-12与烟嘧磺隆竞争乙酰乳酸合酶活性位点，这是安全剂的保护机制。吸收、分布、代谢、排泄和毒性 (ADMET) 预测表明，化合物V-12表现出优于商业化安全剂异恶草醚的药代动力学特性。目标化合物V-12在玉米中表现出较强的除草安全剂活性；因此，它可能是一种潜在的候选化合物，可以帮助进一步保护玉米免受除草剂的损害。

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Design, Synthesis, and Structure–Activity Relationship of Novel Aryl-Substituted Formyl Oxazolidine Derivatives as Herbicide Safeners

Nicosulfuron is the leading herbicide in the global sulfonylurea (SU) herbicide market; it was jointly developed by DuPont and Ishihara. Recently, the widespread use of nicosulfuron has led to increasingly prominent agricultural production hazards, such as environmental harm and influence on subsequent crops. The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of existing herbicides. A series of novel aryl-substituted formyl oxazolidine derivatives were designed using the active group combination method. Title compounds were synthesized using an efficient one-pot method and characterized by infrared (IR) spectrometry, ¹H and ¹³C nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). The chemical structure of compound V-25 was further identified by X-ray single crystallography. The bioactivity assay and structure–activity relationship proved that nicosulfuron phytotoxicity to maize could be reduced by most title compounds. The glutathione S-transferase (GST) activity and acetolactate synthase (ALS) in vivo were determined, and compound V-12 showed inspiring activity comparable to that of the commercial safener isoxadifen-ethyl. The molecular docking model indicated that compound V-12 competed with nicosulfuron for the acetolactate synthase active site and that this is the protective mechanism of safeners. Absorption, distribution, metabolism, excretion, and toxicity (ADMET) predictions demonstrated that compound V-12 exhibited superior pharmacokinetic properties to the commercialized safener isoxadifen-ethyl. The target compound V-12 shows strong herbicide safener activity in maize; thus, it may be a potential candidate compound that can help further protect maize from herbicide damage.

更新日期：2023-05-16

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