588-32-9Relevant articles and documents
Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action
Lei, Kang,Li, Pan,Yang, Xue-Fang,Wang, Shi-Ben,Wang, Xue-Kun,Hua, Xue-Wen,Sun, Bin,Ji, Lu-Sha,Xu, Xiao-Hua
, p. 10489 - 10497 (2019/10/02)
In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
Facile microwave synthesis, structural diversity and herbicidal activity of six novel alkaline-earth metal complexes (AECs) based on skeletal isomerization chlorophenoxyacetic acids
Xu, Xiuling,Hu, Fan,Ma, Yuwei,Gao, Jinming,Shuai, Qi
, p. 4155 - 4166 (2018/03/21)
Six novel AECs of [Sr(o-CPA)2(H2O)4]·(o-CPA) 1, [Ba(o-CPA)2(H2O)]·H2O 2, [Sr(m-CPA)2(H2O)4]·(m-CPA) 3, [Ba(m-CPA)2(H2O)4]2·2(m-CPA)·H2O 4, [Sr(p-CPA)2(H2O)] 5 and [Ba(p-CPA)2(H2O)] 6 (o-CPA = 2-chlorophenoxyacetic acid, m-CPA = 3-chlorophenoxyacetic acid and p-CPA = 4-chlorophenoxyacetic acid) were synthesized by a facile microwave-assistant reaction. The solid-state structures were well established by X-ray crystallography and routine analyses of Fourier transform infrared, elemental analysis, field emission scanning electron microscope (FESEM) and thermogravimetric analysis. The structure data reveal that complexes of 1, 3 and 4 are one-dimensional chains with a zigzag arrangement, while 2, 5 and 6 are (4, 4) rhomboid two-dimensional grid structures. It is noticed that the carboxyl group in these complexes displays multiple coordination modes of μ2-η1:η1 (1, 2, 3, 4, 5 and 6), μ3-η1:η2 (1, 2, 3 and 4), μ2-η1:η2 (2), μ3-η2:η2 (5 and 6). Interestingly, the oxygen atoms of flexible -OCH2- in phenoxy groups take part in coordination behavior with metal centers through the rotation of the C-O and C-C bonds in complexes 2, 5 and 6, while only carboxyl group coordination can be found in complexes 1, 3 and 4. FESEM images indicate that the surface appearances of complexes are totally different from ligands after coordination. All ligands and complexes were evaluated for activity as plant-growth inhibitors against Amaranth (Amaranthus spp.) and barnyard grass. Compared with ligands, complexes 1, 3 and 4 exhibited better response index (RI) values of Shoot elongation against barnyard grass. Moreover, complexes 1, 3 and 4 demonstrated a higher inhibitory activity than 2, 5 and 6. It is significant to develop a new kind of environmentally-friendly herbicide based on these kinds of complexes for their low toxicity and high efficiency.
Calcium coordination compounds based on phenoxyacetic acids: Microwave synthesis, thermostability and influences on the crystal structures of chlorine substituent group on ligands
Xu, Xiuling,Yan, Saisai,Hu, Fan,Zhao, Wei,Shuai, Qi
, p. 541 - 550 (2016/02/26)
Three calcium coordination compounds, [Ca(CPA)(H2O)4]·(CPA), 1, [Ca(MCPA)2(H2O)2]·H2O, 2, and [Ca(TCPA)2(H2O)3]·2H2O, 3 [HCPA = 3-chlorophenoxyacetic acid, HMCPA = 2-methyl-4-chlorophenoxyacetic acid, and HTCPA = 2,4,6-trichlorophenoxyacetic acid], have been synthesized by the microwave method with advantages that include shorter reaction times, lower energy consumption, and higher product yield. The structures have been characterized by IR, elemental analysis, and single-crystal X-ray diffraction. Influences on the crystal structures by changing the number and position of chlorine substituent group in phenoxyacetic acid are discussed. Steric hindrance effects involving the Cl and an ability to form the O-HCl hydrogen bonds enrich the structure diversity. TG analysis reveals that the thermostability for the three compounds is 3 > 1 > 2, which could be influenced by the existence of hydrogen bonds (O-HCl and O-HO).
