- Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
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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.
- Huang, Hao,Liu, Jian-Min,Shu, Lei,Wang, Man-Man,Yan, Yi-Le,Zhang, Da-Yong,Zhang, Jian-Qiu
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supporting information
p. 233 - 247
(2020/03/27)
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- Aromatic oxyacetic acid HPPD inhibitor or salt thereof, weedicide composition, preparation method and application
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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.
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Paragraph 0085; 0089-0091
(2019/10/23)
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- 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 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.
- Wang, Da-Wei,Lin, Hong-Yan,He, Bo,Wu, Feng-Xu,Chen, Tao,Chen, Qiong,Yang, Wen-Chao,Yang, Guang-Fu
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p. 8986 - 8993
(2016/12/09)
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- Synthesis of chiroptical molecular switches by Pd-catalyzed domino reactions
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New photochromic switches based on helical alkenes can quickly and efficiently be accessed by Pd-catalyzed domino reactions using a modular approach; this allows a wide variability in product formation with the advantages of a convergent synthetic route.
- Tietze, Lutz F.,Duefert, Alexander,Lotz, Florian,Soelter, Lars,Oum, Kawon,Lenzer, Thomas,Beck, Tobias,Herbst-Irmer, Regine
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supporting information; experimental part
p. 17879 - 17884
(2010/03/30)
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- COMPOUNDS USEFUL IN THE TREATMENT OF INFLAMMATORY DISEASES
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There are provided according to the invention, novel compounds of formula (I)wherein R, R, R, R, Rand Rare as defined in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.
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