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Synthesis and Herbicidal Activities of Aryloxyacetic Acid Derivatives As HPPD Inhibitors

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Specialty Chemistry
Date 2020 Mar 18
PMID 32180842
Citations 3
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Abstract

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 HPPD (HPPD) inhibitors, in particular compounds ( = 0.011 µM) and ( = 0.012 µM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide ( = 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, exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound 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.

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References
1.
Hall M, Wilks M, Provan W, Eksborg S, Lumholtz B . Pharmacokinetics and pharmacodynamics of NTBC (2-(2-nitro-4-fluoromethylbenzoyl)-1,3-cyclohexanedione) and mesotrione, inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD) following a single dose to healthy male volunteers. Br J Clin Pharmacol. 2001; 52(2):169-77. PMC: 2014534. DOI: 10.1046/j.0306-5251.2001.01421.x. View

2.
Yang C, Pflugrath J, Camper D, Foster M, Pernich D, Walsh T . Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases. Biochemistry. 2004; 43(32):10414-23. DOI: 10.1021/bi049323o. View

3.
Li H, Li L, Li J, Han T, He J, Zhu Y . Novel HPPD inhibitors: triketone 2H-benzo[b][1,4]oxazin-3(4H)-one analogs. Pest Manag Sci. 2017; 74(3):579-589. DOI: 10.1002/ps.4739. View

4.
Borowski T, Bassan A, Siegbahn P . 4-Hydroxyphenylpyruvate dioxygenase: a hybrid density functional study of the catalytic reaction mechanism. Biochemistry. 2004; 43(38):12331-42. DOI: 10.1021/bi049503y. View

5.
Wang W, He H, Zuo N, He H, Peng H, Tan X . Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. J Agric Food Chem. 2012; 60(31):7581-7. DOI: 10.1021/jf301829m. View