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

• Published in: Journal of agricultural and food chemistry 2011-05, Vol.59 (9), p.4801-4813
• Main Authors: He, Hong-Wu, Yuan, Jun-Lin, Peng, Hao, Chen, Ting, Shen, Ping, Wan, Shu-Qing, Li, Yanjun, Tan, Hong-Liang, He, Ya-Hui, He, Jun-Bo, Li, Yan
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; broadleaf weeds; Crop and Animal Protection Chemistry; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Food industries; Fundamental and applied biological sciences. Psychology; herbicidal properties; herbicides; Herbicides - chemical synthesis; Herbicides - chemistry; Herbicides - pharmacology; Molecular Structure; Oryza sativa; Pisum sativum; Plant Proteins - antagonists & inhibitors; Plant Proteins - metabolism; Plants - drug effects; Plants - enzymology; Pyruvate Dehydrogenase Complex - antagonists & inhibitors; Pyruvate Dehydrogenase Complex - metabolism; pyruvic acid; Structure-Activity Relationship; Vigna radiata var. radiata
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf104247w

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.