title: Studies of O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex.
abstract: On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive synthetic modifications were made to the substituents in alkylphosphonate and phenoxy moieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compounds were studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa , was found to be the most effective compound against broadleaf weeds and showed potential utility as herbicide.
authors: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Institute of Pesticide Chemistry, College of Chemistry, Central China Normal University, Wuhan, People's Republic of China. he1208@mail.ccnu.edu.cn
authors: Hong-Wu
authors: HW
authors: He
authors: Jun-Lin
authors: JL
authors: Yuan
authors: Hao
authors: H
authors: Peng
authors: Ting
authors: T
authors: Chen
authors: Ping
authors: P
authors: Shen
authors: Shu-Qing
authors: SQ
authors: Wan
authors: Yanjun
authors: Y
authors: Li
authors: Hong-Liang
authors: HL
authors: Tan
authors: Ya-Hui
authors: YH
authors: He
authors: Jun-Bo
authors: JB
authors: He
authors: Yan
authors: Y
authors: Li
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010940:Plant Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010944:Plants / Q000187:drug effects / Q000201:enzymology; D011768:Pyruvate Dehydrogenase Complex / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D006540:Herbicides; D010940:Plant Proteins; D011768:Pyruvate Dehydrogenase Complex