575-89-3Relevant academic research and scientific papers
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)
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).
Facile synthesis, crystal structure and bioactivity evaluation of two novel barium complexes based on 2,4,6-trichlorophenoxyacetic acid and o-ferrocenylcarbonyl benzoic acid
Xu, Xiuling,Hu, Fan,Shuai, Qi
, p. 13319 - 13326 (2017)
Two novel Ba(ii) complexes [Ba(TCPA)2(H2O)4] 1 and [Ba(H2O)8]·2(o-FcCOC6H4COO)·6H2O 2 [HTCPA = 2,4,6-trichlorophenoxyacetic acid and o-HOOCC6H4-COFc = o-ferrocenylcarbonyl benzoic acid] have been synthesized by a facile microwave method. The solid-state structures were well established by means of X-ray crystallography as well as routine analysis of the infrared spectrum (FTIR), elemental analysis, field emission scanning electron microscopy (FESEM) and thermogravimetric analysis (TG). Different polyhedra of tricapped triangular prisms for 1 and dodecahedra for 2 were present. It is worth noting that the central Ba(ii) ion in 1 is nine-coordinated by two carboxylate oxygen atoms from TCPA ligands and seven oxygen atoms from coordinated water molecules. By contrast, the eight-coordinated Ba(ii) in 2 forms barium-water clusters assembled by O-H?O hydrogen-bonds contributed by coordinated water molecules. The uncoordinated o-OOCC6H4-COFc ligands in 2 play a key role in the process of charge balance. FESEM images exhibited different surface appearances between the ligand and barium complexes, that is: flower-like HTCPA, branch-like o-HOOCC6H4-COFc, block-like complex 1 and corner-truncated cubes for complex 2. The allelopathic activity of the complexes and their corresponding ligands was evaluated against two herbaceous plants of barnyard grass and turnip (Raphanus sativus). All the tested compounds showed certain activity with good RI values. An antifungal bioassay was also carried out in vitro on three strains of Botrytis cinerea Pers., Glomerella cingulata Schr and Cytospora sp. Complex 1 and HTCPA can work against all three tested fungi, whereas o-HOOCC6H4-COFc and 2 only worked for Botrytis cinerea Pers. The complex presented in this paper has potential applications in weed control, and this work provides an experimental basis for future studies on Ba-based pesticides.
Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
Huang, Hao,Liu, Jian-Min,Shu, Lei,Wang, Man-Man,Yan, Yi-Le,Zhang, Da-Yong,Zhang, Jian-Qiu
supporting information, p. 233 - 247 (2020/03/27)
A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.
Aromatic oxyacetic acid HPPD inhibitor or salt thereof, weedicide composition, preparation method and application
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Paragraph 0072; 0076-0078, (2019/10/23)
The invention discloses an aromatic oxyacetic acid HPPD inhibitor shown as a general formula I or II or salt thereof, a weedicide composition, a preparation method and application. The aromatic oxyacetic acid HPPD inhibitor has good weedicidal activity, and the weedicide composition can be prepared into a variety of preparation types for use.
An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
Wang, Da-Wei,Lin, Hong-Yan,He, Bo,Wu, Feng-Xu,Chen, Tao,Chen, Qiong,Yang, Wen-Chao,Yang, Guang-Fu
, p. 8986 - 8993 (2016/12/09)
4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH2Cl2. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity. 2-(2-((1-Bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one, II-13, displayed high, broad-spectrum, and postemergent herbicidal activity at the dosage of 37.5-150 g ai/ha, nearly as potent as mesotrione against some weeds. Furthermore, II-13 showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that II-13 might have potential as a herbicide for weed control in maize and canola fields. II-13 is the first HPPD inhibitor showing good crop safety toward canola.
Eco-friendly microwave synthesis of Mg(II) phenoxy carboxylic acid coordination compounds with specific motifs driven by multiple hydrogen bonding
Xu, Xiuling,Hu, Fan,Yan, Saisai,Lin, Jianguang,Li, Qing,Shuai, Qi
, p. 67610 - 67618 (2016/08/02)
Four novel Mg(ii) coordination compounds [Mg(CPA)2(H2O)4] 1, [Mg(H2O)6]·(MCPA)22, [Mg(DCPA)(H2O)5]·(DCPA) 3 and [Mg(TCPA)2(H2O)4]·2H2O 4 were designed by the strategy of hydrogen bonding driven self-assembly (HCPA = 2-chlorophenoxyacetic acid, HMCPA = 2-methyl-4-chlorophenoxyacetic acid, HDCPA = 2,3-dichlorophenoxyacetic acid and HTCPA = 2,4,6-trichlorophenoxyacetic acid). Single-crystal X-ray diffraction demonstrated that each coordination compound had its own specific motif driven by multiple hydrogen bonding: rectangle motif (compound 1), butterfly motif (compound 2), head and tail connected double heart-rectangle motif (compound 3) and alternative one side shared hexagon-rectangle motif (compound 4). The hydrogen bonding effects (O-H?Cl and O-H?O) on thermostability of the title compounds were well proved by TG analysis. The antibacterial activity of 1-4 has been explored, and all of them showed antibacterial efficiency against colibacillus at certain concentrations. The number of chlorides in the ligands seemed to affect the efficiency of the complexes while their position had no obvious effect. In addition, all the title compounds were evaluated for plant growth regulation by using the lettuce seedling growth bioassay. The results showed that these kinds of compounds had potential to serve as natural plant growth regulators because of their higher allelopathic activity. This research firstly applied the effective microwave method to synthesize Mg(ii) phenoxy carboxylic acid coordination compounds. The design strategy of hydrogen-bonding-driven self-assembly presented here gave a novel insight into the further structural prediction and biofunction achievement of Mg(ii) supramolecular assemblies.
Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.
, p. 199 - 218 (2014/01/06)
In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.
Synthesis, Structure, and Properties of the 2-[5-(Aryloxyacetyl)-Amino-1,3,4-Thiadiazol-2-Ylthio] Propionate Derivatives
Hu, Bing,Zhai, Yue-Yuan,Zhang, Ling,Zhang, You-Ming,Wei, Tai-Bao
, p. 1337 - 1345 (2015/10/29)
A series of novel 2-[5-(aryloxyacetyl)-amino-1,3,4-thiadiazol-2-ylthio] propionate derivatives were synthesized in high yield, and their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis, coupled with one selected single-crystal X-ray structure determination. The herbicidal activities of target compounds were assessed. The preliminary bioassay results showed that some compounds exhibited moderate to strong herbicidal symptoms in preemergence and postemergence tests. At 150 g/ha, S. tritici. show tolerance, while E. crus-galli L., E. Dahuricus, A. retroflexus, and C. glaucum L. were killed or severely injured. The activity of some compounds was comparable to the commercial herbicide 2,4-D. A suitable electron-withdrawing substituent at the 2-and/or 4-position of the phenyl ring was essential for high herbicidal activity. Moreover, the antifungal activities of the compounds have also been studied. The compounds were found to possess broad-spectrum antifungal activity.
Synthesis, antibacterial and antifungal activities of 2,5-disubstituted-1, 3,4-oxadiazoles
Nadagouda,Khochage, Atul,Pradeepkumar,Korat, Haresh,Gadaginamath,Joshi
, p. 85 - 90 (2013/12/04)
A series of 2,5- distributed 1,3,4-oxadiazole derivatives were prepared and evaluated for their antibacterial and antifungal activities. 5-[(2, 4, 6-trichlorophenoxy) methyl]- 1,3,4-oxadiazol-2-thiol 5 was synthesized by the reaction of 2-(2,4,6,-trichlorophenoxy) acetic acid hydrazide 4 with CS 2 and KOH in ethanol. The compound 5 on reaction with ethyl chloroacetate gave ethyl-2-(5-(2,4,6-trichlorophenoxy)methyl)-1,3,4-oxadiazol- 2-ylthio) acetate 6 and this on further hydrolysis by sodium hydroxide, followed by acidification gave 2-(5-((2,4,6-trichlorophenoxy)methyl)-1l3,4-oxadiazol-2- ylthio) acetic acid. 7.The compound 5 on condensation with p-benzoquinone in dry acetone gave 2- (5-((2,4l6-trichlorophenoxy)methyl)-1,3l4-oxadiazol-2-ylthio) benzene-1,4-diol 8.1,3,4- Oxadiazole derivatives 9-15 were prepared by treating hydrazide 4 with aromatic acids, in presence of dehydrating agent. Structures of the newly synthesized compounds were confirmed on the basis of physico-chemical and spectral data. All the synthesized compounds were screened for their antibacterial and antifungal activities using broth micro dilution method. Compounds have shown moderate to good antibacterial and antifungal activities.
Synthesis of 1,1,1-trichloro-2,2-bis-(carboxymethoxyaryl)ethanes as potential antimicrobial and insecticidal agents
Purohit,Shah
, p. 618 - 622 (2007/10/03)
Some new 1,1,1-trichloro-2,2-bis-(carboxymethoxyaryl)-ethanes 2a-t have been synthesised by the treating aryloxyacetic acid (two moles) with chloral hydrate (1 mole) in the presence of catalytic amount of conc. sulphuric acid. The aryloxyacetic acid are prepared by the reaction of substituted phenols with chloroacetic acid in the presence of aq. sodium hydroxide. The antimicrobial activity of these compounds have been assayed against various Gram+ve, Gram-ve bacteria and fungi. The constitution of the products have been elucidated by IR, 1H NMR and mass spectral data and elemental analyses.
