9 research outputs found

    Assembly and Selective Photocatalysis of Two Multifunctional Copper(II) Complexes Derived From a Bis-Pyridyl-Bis-Amide and Two Dicarboxylates

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    <p>Two multifunctional metal-organic coordination polymers, namely [Cu(4-bpah)(2,6-PDA)] (<b>1</b>) and [Cu(4-bpah)(3-NIP)]·H<sub>2</sub>O (<b>2</b>), where 4-bpah = <i>N, N</i>′-bis(4-pyridinecarboxamide)-1,2-cyclohexane, 2,6-H<sub>2</sub>PDA = pyridine-2,6-dicarboxylic acid, 3-H<sub>2</sub>NIP = 3-nitrophalic acid, have been hydrothermally synthesized and structurally characterized by IR, TG, and single-crystal X-ray diffraction analyses. Complex <b>1</b> is a 1D infinite helix chain structure. Complex <b>2</b> possesses a 2D polymeric layer containing two kinds of <i>meso</i>-helical chains: [Cu-4-bpah]<sub>n</sub> and [Cu-3-NIP]<sub>n</sub>. The adjacent 1D chains for <b>1</b> or the adjacent 2D layers for <b>2</b> are further linked by hydrogen bonding interactions to form 2D or 3D supramolecular networks, respectively. The fluorescent, electrochemical and photocatalytic properties of complexes <b>1–2</b> have also been investigated.</p

    An Effective Strategy To Construct Novel Polyoxometalate-Based Hybrids by Deliberately Controlling Organic Ligand Transformation <i>In Situ</i>

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    Deliberately controlling organic ligand transformation <i>in situ</i> has remained a challenge for the construction of polyoxometalate (POM)-based inorganic–organic hybrids. In this work, four POM-based hybrids assembled from an <i>in situ</i> bifurcating organic ligand[Cu<sub>2</sub>(DIBA)<sub>4</sub>]­(H<sub>3</sub>PMo<sub>12</sub>O<sub>40</sub>)·6H<sub>2</sub>O (<b>1</b>), [Cu<sub>2</sub>(DIBA)<sub>4</sub>]­(H<sub>4</sub>SiW<sub>12</sub>O<sub>40</sub>)·6H<sub>2</sub>O (<b>2</b>), [Ag­(HDIBA)<sub>2</sub>]­(H<sub>2</sub>PMo<sub>12</sub>O<sub>40</sub>)·2H<sub>2</sub>O (<b>3</b>), [Ag<sub>3</sub>(HDIBA)<sub>2</sub>(H<sub>2</sub>O)]­[(P<sub>2</sub>W<sub>18</sub>O<sub>62</sub>)<sub>1/2</sub>]·4H<sub>2</sub>O (<b>4</b>) (DIBAH = 3,5-di­(1H-imidazol-1-yl) benzoic acid)have been designed and obtained under hydrothermal conditions. Compounds <b>1</b> and <b>2</b> are isostructural, displaying a three-dimensional (3D) 2-fold interpenetrating framework with two types of channels, and the bigger channels are occupied by Keggin polyoxoanions and crystallization water molecules, but only crystallization water molecules in the smaller ones. Compound <b>3</b> displays a 3D supramolecular structure constructed from {Ag­(HDIBA)<sub>2</sub>} segments and PMo<sub>12</sub>O<sub>40</sub><sup>3–</sup> polyoxoanions through hydrogen bonding interactions. Compound <b>4</b> shows a 3D 2-fold interpenetrating framework based on (3, 3, 4)-connected network, which is constructed from {Ag<sub>3</sub>(HDIBA)<sub>2</sub>}<sub><i>n</i></sub> chains and P<sub>2</sub>W<sub>18</sub>O<sub>62</sub><sup>6–</sup> polyoxoanions as linkers. The DIBAH ligand was generated <i>in situ</i> from 3,5-di­(1H-imidazol-1-yl)­benzonitrile by deliberate design, which illustrates that the strategy to construct novel POM-based hybrids by controlling ligand transformation <i>in situ</i> is rational and feasible. In addition, the effects of the central metal and POMs on the structures of the target compounds were discussed. Finally, the electrochemical and photocatalytic properties of compounds <b>1</b>–<b>4</b> have been investigated in this paper

    Various Polycarboxylate-Directed Cd(II) Coordination Polymers Based on a Semirigid Bis-pyridyl-bis-amide Ligand: Construction and Fluorescent and Photocatalytic Properties

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    Nine new Cd­(II) coordination polymers (CPs) including [Cd<sub>3</sub>(4-bmbpd)<sub>4</sub>­Cl<sub>6</sub>(H<sub>2</sub>O)<sub>2</sub>] (<b>1</b>), [Cd­(4-bmbpd)­(2,2′-BDC)­(H<sub>2</sub>O)] (<b>2</b>), [Cd­(4-bmbpd)­(OBA)]­·H<sub>2</sub>O (<b>3</b>), [Cd­(4-bmbpd)<sub>0.5</sub>­(ADTZ)­(H<sub>2</sub>O)]­·H<sub>2</sub>O (<b>4</b>), [Cd<sub>4</sub>(4-bmbpd)­(1,3-ATDC)<sub>4</sub>­(H<sub>2</sub>O)<sub>6</sub>]­·2H<sub>2</sub>O (<b>5</b>), [Cd­(4-bmbpd)­(3-NPH)­(H<sub>2</sub>O)]­·H<sub>2</sub>O (<b>6</b>), [Cd­(4-bmbpd)<sub>0.5</sub>­(NIP)­(H<sub>2</sub>O)] (<b>7</b>), [Cd­(4-bmbpd)<sub>0.5</sub>­(HIP)]­·H<sub>2</sub>O (<b>8</b>), and [Cd<sub>3</sub>(4-bmbpd)<sub>2</sub>­(1,3,5-BTC)­(H<sub>2</sub>O)<sub>4</sub>]­·4H<sub>2</sub>O (<b>9</b>) (4-bmbpd = <i>N</i>,<i>N</i>′-bis­(4-methylenepyridin-4-yl)-1,4-benzenedicarboxamide, 2,2′-H<sub>2</sub>BDC = 2,2′-biphenyldicarboxylic acid, H<sub>2</sub>OBA = 4,4′-oxybis­(benzoic acid, H<sub>2</sub>ADTZ = 2,5-(s-acetic acid)­dimercapto-1,3,4-thiadiazole, 1,3-H<sub>2</sub>ATDC = 1,3-adamantanedicarboxylic acid, 3-H<sub>2</sub>NPH = 3-nitrophthalic acid, H<sub>2</sub>NIP = 5-nitroisophthalic acid, H<sub>2</sub>HIP = 5-hydroxyisophthalic acid, and 1,3,5- H<sub>3</sub>BTC = 1,3,5-benzenetricarboxylic acid), have been produced with a hydrothermal/solvothermal technique and structurally characterized by single-crystal X-ray diffraction, powder X-ray diffraction, thermogravimetric analysis, and infrared spectroscopy. Complex <b>1</b> exhibits a one-dimensional (1D) wave-like double chain constructed from [Cd<sub>3</sub>(4-bmbpd)<sub>2</sub>­Cl<sub>6</sub>(H<sub>2</sub>O)<sub>2</sub>] subunits and μ<sub>2</sub>-bridging 4-bmbpd ligands. <b>2</b> is a two-dimensional (2D) 4-connected layer consisting of 1D [Cd-4-bmbpd]<sub><i>n</i></sub> zigzag chains and 1D [Cd-2,2′-BDC]<sub><i>n</i></sub> single-strand helix chains. Complex <b>3</b> is also a 2D 4-connected network constituted of 1D [Cd-OBA]<sub><i>n</i></sub> linear chains and [Cd­(4-bmbpd)]<sub><i>n</i></sub> wave-like chains. Complex <b>4</b> has a (2,4,4)-connected 2D architecture based on [Cd<sub>2</sub>(ADTZ)<sub>2</sub>] rings and μ<sub>4</sub>-bridging 4-bmbpd ligands with {4<sup>2</sup>·8<sup>2</sup>·10<sup>2</sup>}­{ 4<sup>2</sup>·8<sup>4</sup>}<sub>2</sub>{4}<sub>2</sub> topology. Complex <b>5</b> exhibits an intriguing 1D chain constructed from [Cd<sub>4</sub>(1,3-ATDC)<sub>4</sub>] rings and μ<sub>2</sub>/μ<sub>4</sub>-bridging 4-bmbpd ligands. Complex <b>6</b> presents a 1D ladder-shaped chain. Complex <b>7</b> displays a 3D (4,4)-connected framework giving an interesting self-penetrating structure. Complex <b>8</b> is a 3D (4,5)-connected architecture with {4<sup>4</sup>·6<sup>2</sup>}­{4<sup>4</sup>·6<sup>6</sup>} topology. <b>9</b> shows a 3D (2,3,4,4)-connected framework, which contains [Cd-1,3,5-BTC]<sub><i>n</i></sub> 1D double chains. The versatile structures reveal the impact of the carboxyl position and number, the flexibility, as well as the functional groups of polycarboxylate auxiliary ligands on the architectures. Furthermore, the effects of different organic solvents on the fluorescent behaviors of <b>1</b>–<b>4</b> and <b>7</b>–<b>9</b>, and the photocatalytic properties of <b>1</b>–<b>9</b> under UV irradiation, were studied

    Structural Diversities and Fluorescent and Photocatalytic Properties of a Series of Cu<sup>II</sup> Coordination Polymers Constructed from Flexible Bis-pyridyl-bis-amide Ligands with Different Spacer Lengths and Different Aromatic Carboxylates

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    Thirteen new Cu<sup>II</sup> coordination polymers, namely, [Cu­(3-dppa)­(1,3,5-HBTC)] (<b>1</b>), [Cu­(3-dpha)­(1,3,5-HBTC)­(H<sub>2</sub>O)]­·H<sub>2</sub>O (<b>2</b>), [Cu<sub>3</sub>(3-dpsea)­(1,3,5-BTC)<sub>2</sub>­(H<sub>2</sub>O)<sub>5</sub>]·4H<sub>2</sub>O (<b>3</b>), [Cu­(3-dpba)­(1,2-BDC)]­·H<sub>2</sub>O (<b>4</b>), [Cu­(3-dpha)­(1,2-BDC)] (<b>5</b>), [Cu­(3-dpsea)­(1,2-BDC)]­·H<sub>2</sub>O (<b>6</b>), [Cu<sub>2</sub>(3-dpyp)­(1,3-BDC)<sub>2</sub>­(H<sub>2</sub>O)<sub>4</sub>]­·3H<sub>2</sub>O (<b>7</b>), [Cu­(3-dppa)­(1,3-BDC)­(H<sub>2</sub>O)]­·2H<sub>2</sub>O (<b>8</b>), [Cu­(3-dppia)­(1,3-BDC)­(H<sub>2</sub>O)<sub>2</sub>]­·2H<sub>2</sub>O (<b>9</b>), [Cu<sub>2</sub>(3-dpsea)<sub>2</sub>­(1,3-BDC)<sub>2</sub>­(H<sub>2</sub>O)<sub>2</sub>]­·7H<sub>2</sub>O (<b>10</b>), [Cu­(3-dpba)­(1,4-NDC)]­·3H<sub>2</sub>O (<b>11</b>), [Cu­(3-dpyh)­(1,4-NDC)­(H<sub>2</sub>O)]­·3H<sub>2</sub>O (<b>12</b>), [Cu­(3-dpyh)<sub>0.5</sub>­(1,4-NDC)]­·H<sub>2</sub>O (<b>13</b>), have been purposefully synthesized under hydrothermal conditions [3-dppa = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­propanediamide, 3-dpba = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­butanediamide, 3-dpha = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­hexanedioicdiamide, 3-dppia = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­pimelicdiamide, 3-dpsea = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­sebacicdiamide, 3-dpyp = <i>N</i>,<i>N</i>′-di­(3-pyridine­carboxamide)-1,3-propane, 3-dpyh = <i>N</i>,<i>N</i>′-di­(3-pyridine­carboxamide)-1,6-hexane, 1,3,5-H<sub>3</sub>BTC = 1,3,5-benzenetricarboxylic acid, 1,2-H<sub>2</sub>BDC = 1,2-benzenedicarboxylic acid, 1,3-H<sub>2</sub>BDC = 1,3-benzenedicarboxylic acid and 1,4-H<sub>2</sub>NDC = 1,4-naphthalenedicarboxylic acid]. Complexes <b>1</b>–<b>3</b> based on the same auxiliary ligand show various structures. Complex <b>1</b> features a one-dimensional (1D) ∞-like double-chain structure, which consists of a [Cu-1,3,5-HBTC]<sub><i>n</i></sub> chain and [Cu-3-dppa]<sub><i>n</i></sub> <i>meso</i>-helical chain. Complex <b>2</b> possesses a (2,4) undulated honeycomb (hcb) net. Complex <b>3</b> is a 3-fold interpenetrating three-dimensional (3D) framework, which shows trinodal (2,3,3)-connected topology with the Schläfli symbol of (10·12<sup>2</sup>)<sub>2</sub>(10<sup>3</sup>)<sub>2</sub>(12). Complexes <b>4</b>–<b>6</b> with 1,2-BDC as secondary ligand exhibit different two-dimensional (2D) layer structures. Complex <b>4</b> exhibits a 2D (2,4)-connected (4·12<sup>4</sup>·14)­(4) net. Complexes <b>5</b> and <b>6</b> have similar structures and show 2D networks with undulated sql topology. For complexes <b>7</b>–<b>10</b> based on 1,3-BDC secondary ligand, complex <b>7</b> shows a 1D zigzag chain, while complexes <b>8</b>–<b>10</b> have similar wave-like 2D structures. When 1,4-NDC was used as the auxiliary ligand, complex <b>11</b> is a 2D puckered (4,4) network, complex <b>12</b> reveals a 4-connected topology with the point symbol of (4<sup>4</sup>·6<sup>2</sup>), while complex <b>13</b> exhibits a 3-fold interpenetrating 3D α-Po framework. The structural diversity indicates that the bis-pyridyl-bis-amide ligands with different spacers and the aromatic polycarboxylates play important roles in tuning the dimensionalities and structures of the title complexes. The fluorescent and photocatalytic properties for <b>1</b>–<b>13</b> have also been investigated in detail

    Structural Diversities and Fluorescent and Photocatalytic Properties of a Series of Cu<sup>II</sup> Coordination Polymers Constructed from Flexible Bis-pyridyl-bis-amide Ligands with Different Spacer Lengths and Different Aromatic Carboxylates

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    Thirteen new Cu<sup>II</sup> coordination polymers, namely, [Cu­(3-dppa)­(1,3,5-HBTC)] (<b>1</b>), [Cu­(3-dpha)­(1,3,5-HBTC)­(H<sub>2</sub>O)]­·H<sub>2</sub>O (<b>2</b>), [Cu<sub>3</sub>(3-dpsea)­(1,3,5-BTC)<sub>2</sub>­(H<sub>2</sub>O)<sub>5</sub>]·4H<sub>2</sub>O (<b>3</b>), [Cu­(3-dpba)­(1,2-BDC)]­·H<sub>2</sub>O (<b>4</b>), [Cu­(3-dpha)­(1,2-BDC)] (<b>5</b>), [Cu­(3-dpsea)­(1,2-BDC)]­·H<sub>2</sub>O (<b>6</b>), [Cu<sub>2</sub>(3-dpyp)­(1,3-BDC)<sub>2</sub>­(H<sub>2</sub>O)<sub>4</sub>]­·3H<sub>2</sub>O (<b>7</b>), [Cu­(3-dppa)­(1,3-BDC)­(H<sub>2</sub>O)]­·2H<sub>2</sub>O (<b>8</b>), [Cu­(3-dppia)­(1,3-BDC)­(H<sub>2</sub>O)<sub>2</sub>]­·2H<sub>2</sub>O (<b>9</b>), [Cu<sub>2</sub>(3-dpsea)<sub>2</sub>­(1,3-BDC)<sub>2</sub>­(H<sub>2</sub>O)<sub>2</sub>]­·7H<sub>2</sub>O (<b>10</b>), [Cu­(3-dpba)­(1,4-NDC)]­·3H<sub>2</sub>O (<b>11</b>), [Cu­(3-dpyh)­(1,4-NDC)­(H<sub>2</sub>O)]­·3H<sub>2</sub>O (<b>12</b>), [Cu­(3-dpyh)<sub>0.5</sub>­(1,4-NDC)]­·H<sub>2</sub>O (<b>13</b>), have been purposefully synthesized under hydrothermal conditions [3-dppa = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­propanediamide, 3-dpba = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­butanediamide, 3-dpha = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­hexanedioicdiamide, 3-dppia = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­pimelicdiamide, 3-dpsea = <i>N</i>,<i>N</i>′-di­(3-pyridyl)­sebacicdiamide, 3-dpyp = <i>N</i>,<i>N</i>′-di­(3-pyridine­carboxamide)-1,3-propane, 3-dpyh = <i>N</i>,<i>N</i>′-di­(3-pyridine­carboxamide)-1,6-hexane, 1,3,5-H<sub>3</sub>BTC = 1,3,5-benzenetricarboxylic acid, 1,2-H<sub>2</sub>BDC = 1,2-benzenedicarboxylic acid, 1,3-H<sub>2</sub>BDC = 1,3-benzenedicarboxylic acid and 1,4-H<sub>2</sub>NDC = 1,4-naphthalenedicarboxylic acid]. Complexes <b>1</b>–<b>3</b> based on the same auxiliary ligand show various structures. Complex <b>1</b> features a one-dimensional (1D) ∞-like double-chain structure, which consists of a [Cu-1,3,5-HBTC]<sub><i>n</i></sub> chain and [Cu-3-dppa]<sub><i>n</i></sub> <i>meso</i>-helical chain. Complex <b>2</b> possesses a (2,4) undulated honeycomb (hcb) net. Complex <b>3</b> is a 3-fold interpenetrating three-dimensional (3D) framework, which shows trinodal (2,3,3)-connected topology with the Schläfli symbol of (10·12<sup>2</sup>)<sub>2</sub>(10<sup>3</sup>)<sub>2</sub>(12). Complexes <b>4</b>–<b>6</b> with 1,2-BDC as secondary ligand exhibit different two-dimensional (2D) layer structures. Complex <b>4</b> exhibits a 2D (2,4)-connected (4·12<sup>4</sup>·14)­(4) net. Complexes <b>5</b> and <b>6</b> have similar structures and show 2D networks with undulated sql topology. For complexes <b>7</b>–<b>10</b> based on 1,3-BDC secondary ligand, complex <b>7</b> shows a 1D zigzag chain, while complexes <b>8</b>–<b>10</b> have similar wave-like 2D structures. When 1,4-NDC was used as the auxiliary ligand, complex <b>11</b> is a 2D puckered (4,4) network, complex <b>12</b> reveals a 4-connected topology with the point symbol of (4<sup>4</sup>·6<sup>2</sup>), while complex <b>13</b> exhibits a 3-fold interpenetrating 3D α-Po framework. The structural diversity indicates that the bis-pyridyl-bis-amide ligands with different spacers and the aromatic polycarboxylates play important roles in tuning the dimensionalities and structures of the title complexes. The fluorescent and photocatalytic properties for <b>1</b>–<b>13</b> have also been investigated in detail

    Spacers-directed structural diversity of Co(II)/Zn(II) complexes based on S-/O-bridged dipyridylamides: electrochemical, fluorescent recognition behavior and photocatalytic properties

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    <p>To investigate the effect of the spacers of S-/O-bridged dipyridylamides on the structures of Co(II)/Zn(II) complexes, [Co(L<sup>1</sup>)(chda)]·1.5H<sub>2</sub>O (<b>CP1</b>), [Co(L<sup>2</sup>)(chda)] (<b>CP2</b>), [Zn(L<sup>1</sup>)(hip)]·DMA·2H<sub>2</sub>O (<b>CP3</b>), and [Zn(L<sup>2</sup>)(hip)]·2.8H<sub>2</sub>O (<b>CP4</b>) [L<sup>1</sup> = <i>N,N′</i>-bis(pyridine-3-yl)thiophene-2,5-dicarboxamide, H<sub>2</sub>chda = <i>trans</i>-1,4-cyclohexanedicarboxylic acid, L<sup>2</sup> = <i>N,N′</i>-bis(pyridine-3-yl)-4,4′-oxybis(benzoic) dicarboxamide, H<sub>2</sub>hi<i>p</i> = 5-hydroxyisophthalic acid, DMA = <i>N,N</i>-dimethylacetamide], have been solvothermally synthesized. X-ray single-crystal diffraction shows that <b>CP1</b> is a 2-D 3,5-connected network based on Co-L<sup>1</sup> linear chains and (Co-chda)<sub>2</sub> double chains. <b>CP2</b> features a 1-D structure derived from 1-D wave-like (Co-chda)<sub>2</sub> double chains decorated by terminal L<sup>2</sup> ligands. <b>CP3</b> and <b>CP4</b> show wave-like (4,4) networks constructed by 1-D Zn-L<sup>1</sup> zigzag and Zn-hip zigzag (for <b>CP3</b>)/linear (for <b>CP4</b>) chains. The effect of the spacers of S-/O-bridged dipyridylamides on the structures of the title complexes was discussed. Electrochemical behaviors of <b>CP1</b>–<b>CP2</b> and solid-state luminescent properties of <b>CP3</b>–<b>CP4</b> were studied. The luminescence investigations show that <b>CP3</b> and <b>CP4</b> are recycled fluorescent probes for environmentally relevant Fe<sup>3+</sup> ions. The photocatalytic properties for the degradation of methylene blue (MB) under ultraviolet light irradiation of <b>CP3</b>–<b>CP4</b> and the recyclable materials after fluorescent sensing Fe<sup>3+</sup> ions (named <b>CP3</b>@Fe<sup>3+</sup> and <b>CP4</b>@Fe<sup>3+</sup>) have also been investigated.</p

    Discovery of Subnanomolar Inhibitors of 4‑Hydroxyphenylpyruvate Dioxygenase via Structure-Based Rational Design

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    High-potency 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are usually featured by time-dependent inhibition. However, the molecular mechanism underlying time-dependent inhibition by HPPD inhibitors has not been fully elucidated. Here, based on the determination of the HPPD binding mode of natural products, the π–π sandwich stacking interaction was found to be a critical element determining time-dependent inhibition. This result implied that, for the time-dependent inhibitors, strengthening the π–π sandwich stacking interaction might improve their inhibitory efficacy. Consequently, modification with one methyl group on the bicyclic ring of quinazolindione inhibitors was achieved, thereby strengthening the stacking interaction and significantly improving the inhibitory efficacy. Further introduction of bulkier hydrophobic substituents with higher flexibility resulted in a series of HPPD inhibitors with outstanding subnanomolar potency. Exploration of the time-dependent inhibition mechanism and molecular design based on the exploration results are very successful cases of structure-based rational design and provide a guiding reference for future development of HPPD inhibitors

    An Efficient One-Pot Synthesis of 2‑(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4‑Hydroxyphenylpyruvate Dioxygenase Inhibitors

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    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 <i>N</i>,<i>N</i>′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH<sub>2</sub>Cl<sub>2</sub>. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (<i>At</i>HPPD) inhibitory activity. 2-(2-((1-Bromonaphthalen-2-yl)­oxy)­acetyl)-3-hydroxycyclohex-2-en-1-one, <b>II-13</b>, 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, <b>II-13</b> showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that <b>II-13</b> might have potential as a herbicide for weed control in maize and canola fields. <b>II-13</b> is the first HPPD inhibitor showing good crop safety toward canola

    Synthesis and Herbicidal Activity of Triketone–Quinoline Hybrids as Novel 4‑Hydroxyphenylpyruvate Dioxygenase Inhibitors

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    4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone–quinoline hybrids were designed and subsequently optimized on the basis of the structure–activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (<i>At</i>HPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound <b>III-l</b>, 3-hydroxy-2-(2-methoxy-7-(methylthio)­quinoline-3-carbonyl)­cyclohex-2-enone (<i>K</i><sub>i</sub> = 0.009 μM, <i>At</i>HPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound <b>III-l</b> was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone–quinoline hybrids may serve as new lead structures for novel herbicide discovery
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