title: An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors.
abstract: 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.
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Da-Wei
authors.initials: DW
authors.lastname: Wang
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Hong-Yan
authors.initials: HY
authors.lastname: Lin
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Bo
authors.initials: B
authors.lastname: He
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Feng-Xu
authors.initials: FX
authors.lastname: Wu
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Tao
authors.initials: T
authors.lastname: Chen
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Qiong
authors.initials: Q
authors.lastname: Chen
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.
authors.forename: Wen-Chao
authors.initials: WC
authors.lastname: Yang
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, People's Republic of China.|Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 30071, People's Republic of China.
authors.forename: Guang-Fu
authors.initials: GF
authors.lastname: Yang
mesh_terms: D015111:4-Hydroxyphenylpyruvate Dioxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D017360:Arabidopsis / Q000187:drug effects; D029741:Brassica rapa / Q000187:drug effects; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005021:Ethylamines / Q000737:chemistry; D006540:Herbicides / Q000138:chemical synthesis*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis*; D009570:Nitriles / Q000737:chemistry; D057685:Plant Weeds / Q000187:drug effects; D013329:Structure-Activity Relationship; D058728:Weed Control; D003313:Zea mays / Q000187:drug effects
chemical_list: C000617953:2-(2-((1-bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one; D003512:Cyclohexanones; D004791:Enzyme Inhibitors; D005021:Ethylamines; D006540:Herbicides; D007093:Imidazoles; D009281:Naphthalenes; D009570:Nitriles; C432907:mesotrione; C006900:N,N-carbonyldiimidazole; C010833:acetone cyanohydrin; D015111:4-Hydroxyphenylpyruvate Dioxygenase; C016162:triethylamine
keywords: 4-hydroxyphenylpyruvate dioxygenase; herbicidal activity; one-pot synthesis; structure−activity relationship; triketone