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Molecules 2015, 20(1), 1088-1103;

Synthesis and Herbicidal Activity of Novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl Carboxylic Esters

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
Department of Fundamental Science, Beijing University of Agriculture, Beijing 102206, China
Novo Nordisk, Inc., Princeton, NJ 08540, USA
These authors contributed equally to this works.
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 14 November 2014 / Accepted: 16 December 2014 / Published: 12 January 2015
(This article belongs to the Section Organic Chemistry)
Full-Text   |   PDF [717 KB, uploaded 12 January 2015]   |  


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. View Full-Text
Keywords: carboxylic esters; IGPD; synthesis; herbicidal activity carboxylic esters; IGPD; synthesis; herbicidal activity

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Jin, Y.; Zhao, H.; Lu, H.; Kuemmel, C.M.; Zhang, J.; Wang, D. Synthesis and Herbicidal Activity of Novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl Carboxylic Esters. Molecules 2015, 20, 1088-1103.

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