title: Synthesis and herbicidal activity of novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl carboxylic esters.
abstract: A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1H-1,2,3-triazol-1-yl)propan-2-yl carboxylic esters, were designed on the basis of the diazafulvene intermediate of imidazole glycerol phosphate dehydratase (IGPD) and high-activity inhibitors of IGPD, and synthesized as inhibitors targeting IGPD in plants. Their structures were confirmed by 1H-NMR, 13C-NMR, 31P-NMR and HR-MS. The herbicidal evaluation performed by a Petri dish culture method showed that most compounds possessed moderate to good herbicidal activities. Six compounds were chosen for further herbicidal evaluation on barnyard grass by pot experiments. 1-(Diethoxyphosphoryl)-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propan-2-yl 2-(naphthalen-1-yl)acetate (5-A3) and ethyl 1-(2-acetoxy-3-(diethoxyphosphoryl)propyl)-1H-1,2,3-triazole-4-carboxylate (5-B4) showed good herbicidal activities. Compared with the compounds with the best herbicidal activity ever reported, both compounds 5-A3 and 5-B4, which can inhibit the growth of barnyard grass at the concentration of 250g/hm2, efficiently gave rise to a nearly 4-fold increase of the herbicidal potency. However, their herbicidal activities were lower than that of acetochlor (62.5 g/hm2) in the pot experiments.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. walterjin@126.com.
authors.forename: Yan
authors.initials: Y
authors.lastname: Jin
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. zhaohanqing@bua.edu.cn.
authors.forename: Hanqing
authors.initials: H
authors.lastname: Zhao
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. luhz@cau.edu.cn.
authors.forename: Huizhe
authors.initials: H
authors.lastname: Lu
authors.affiliation: Novo Nordisk, Inc., Princeton, NJ 08540, USA. colleenkuemmel@gmail.com.
authors.forename: Colleen M
authors.initials: CM
authors.lastname: Kuemmel
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. zhangjianjun@cau.edu.cn.
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. wangdq@cau.edu.cn.
authors.forename: Daoquan
authors.initials: D
authors.lastname: Wang
mesh_terms: D029741:Brassica rapa / Q000187:drug effects; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002264:Carboxylic Acids / Q000737:chemistry* / Q000494:pharmacology; D004952:Esters / Q000737:chemistry; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013058:Mass Spectrometry; D066244:Proton Magnetic Resonance Spectroscopy; D014908:Triticum / Q000187:drug effects
chemical_list: D002264:Carboxylic Acids; D004952:Esters; D006540:Herbicides