伪-(Substituted-phenoxyacetoxy)-伪-heterocyclylmethylphosphonates: Synthesis, Herbicidal Activity, Inhibition on Pyruvate Dehydrogenase Complex (PDHc), and Application as Postemergent Herbicide against
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- 作者：Hong-Wu He ; Hao Peng ; Tao Wang ; Chubei Wang ; Jun-Lin Yuan ; Ting Chen ; Junbo He ; Xiaosong Tan
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2013
- 出版时间：March 13, 2013
- 年：2013
- 卷：61
- 期：10
- 页码：2479-2488
- 全文大小：325K
- 年卷期：v.61,no.10(March 13, 2013)
- ISSN：1520-5118
文摘
Pyruvate dehydrogenase complex (PDHc) is the site of action of a new class of herbicides. On the basis of the previous work for O,O鈥?dimethyl 伪-(substituted-phenoxyacetoxy)alkylphosphonates (I), further synthetic modifications were made by introducing a fural and a thienyl group to structure I. A series of 伪-(substituted-phenoxyacetoxy)-伪-heterocyclylmethylphosphonate derivatives (II) were synthesized as potential inhibitors of PDHc. The postemergent activity of the title compounds II was evaluated in greenhouse experiments. The in vitro efficacy of II against PDHc was also examined. Compounds II with fural as R3 and 2,4-dichloro as X and Y showed significant herbicidal activity and effective inhibition against PDHc from plants. O,O鈥?Dimethyl 伪-(2,4-dichlorophenoxyacetoxy)-伪-(furan-2-yl)methylphosphonate II-17 had higher inhibitory potency against PDHc from Pisum sativum than against PDHc from Oryza sativa in vitro and was most effective against broadleaf weeds at 50 and 300 ai g/ha. II-17 was safe for maize and rice even at the dose of 900鈥?200 ai g/ha. Field trials at different regions in China showed that II-17 (HWS) could control a broad spectrum of broad-leaved and sedge weeds at the rate of 225鈥?75 ai g/ha for postemergent applications in maize fields. II-17 (HWS) displayed potential utility as a selective herbicide.