Synthesis of Novel Diphenyl Ether Herbicides

Sumida, Motoo; Niwata, Shinjiro; Fukami, Hironobu; Tanaka, Takaharu; Wakabayashi, Katsunori; Böger, Peter

doi:10.1021/jf00055a032

Cited by 14 publications

(3 citation statements)

References 7 publications

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“…2 Many of these DPE analogues are (or have been) successful commercial herbicides 1. Structure‐activity relationship (SAR) studies on DPE herbicides published previously3–10 used whole‐plant biological activity. However, in vivo biological activity data are not useful if one is interested in understanding the relationship between structural characteristics of inhibitors and their molecular binding site.…”

Section: Introductionmentioning

confidence: 99%

Are you fit for purpose? The development of a competency framework for diabetes nursing in the UK

Hill¹

2011

European Diabetes Nursing

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Hard and soft centers: the donors O (hard), P and C (soft) are together in the multidentate, oxygen‐substituted, anionic phosphanes I and II, which are particularly suitable for the synthesis of novel calcium organyls. With these mono‐ and dianionic ligands calcium organyl compounds, without cyclopentadiene ligands, could be prepared and structurally characterized: a sodium trialkyl calcate(II) and the first calcium organyl compound with a heterocubane structure. Ph′=p‐tolyl.

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Section: Introductionmentioning

confidence: 99%

Are you fit for purpose? The development of a competency framework for diabetes nursing in the UK

Hill¹

2011

European Diabetes Nursing

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“…[5][6][7][8] Heterocyclic phenyl ethers are highly active both pre-and postemergence on a wide variety of weeds. [9][10][11][12][13][14][15][16][17] A few recently reported examples include 6-aryloxy-1H-benzotriazoles, 18 aryloxyindolin-2-(3H)-ones, 5-aryloxybenzisoxazoles, 6-aryloxyquinoxalin-2,3-diones, benzoheterocycles, [19][20][21] and benzoxazines. 22 Through studying the structure-activity relationships of heterocyclic phenyl ethers, we added an ester or an acylamide on N-3 of quinzaolinediones to improve the activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and herbicidal activity of 1,3-substituted quinazolinedione derivatives

Yu¹,

Wu²,

Cui³

et al. 2008

Arkivoc

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Quinazolinediones derivatives are a new family of diphenyl ether herbicides. Twenty four 1,3-substituted quinazolinediones derivatives were designed and synthesized. Their structures were confirmed by 1 H NMR and elemental analysis. The preliminary bioassay results show that most of these compounds have herbicidal activity in post-emergence treatment. The compounds 3c, 3d, 3e, 3f showed 90-100% herbicidal efficacy at 200 gha -1 against dicotyledonous weeds such as Abutilon theophrasti.

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“…Structure-activity relationship (SAR) studies on diphenyl-ether herbicides have been extensively reported [29][30][31]. Previous QSARs performed at two or multidimensional level reproduced the activity of individual data sets relatively well.…”

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confidence: 99%

Structure–activity relationships of diphenyl-ether as protoporphyrinogen oxidase inhibitors: insights from computational simulations

Hao

Tan

et al. 2011

J Comput Aided Mol Des

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Protoporphyrinogen oxidase (PPO, EC 1.3.3.4), which has been identified as a significant target for a great family of herbicides with diverse chemical structures, is the last common enzyme responsible for the seventh step in the biosynthetic pathway to heme and chlorophyll. Among the existing PPO inhibitors, diphenyl-ether is the first commercial family of PPO inhibitors and used as agriculture herbicides for decades. Most importantly, diphenyl-ether inhibitors have been found recently to possess the potential in Photodynamic therapy (PDT) to treat cancer. Herein, molecular dynamics simulations, approximate free energy calculations and hydrogen bond energy calculations were integrated together to uncover the structure-activity relationships of this type of PPO inhibitors. The calculated binding free energies are correlated very well with the values derived from the experimental k (i) data. According to the established computational models and the results of approximate free energy calculation, the substitution effects at different position were rationalized from the view of binding free energy. Some outlier (e.g. LS) in traditional QSAR study can also be explained reasonably. In addition, the hydrogen bond energy calculation and interaction analysis results indicated that the carbonyl oxygen on position-9 and the NO(2) group at position-8 are both vital for the electrostatic interaction with Arg98, which made a great contribution to the binding free energy. These insights from computational simulations are not only helpful for understanding the molecular mechanism of PPO-inhibitor interactions, but also beneficial to the future rational design of novel promising PPO inhibitors.

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Synthesis of Novel Diphenyl Ether Herbicides

Cited by 14 publications

References 7 publications

Are you fit for purpose? The development of a competency framework for diabetes nursing in the UK

Are you fit for purpose? The development of a competency framework for diabetes nursing in the UK

Synthesis and herbicidal activity of 1,3-substituted quinazolinedione derivatives

Structure–activity relationships of diphenyl-ether as protoporphyrinogen oxidase inhibitors: insights from computational simulations

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