Next Article in Journal
Novel Pyrazine Analogs of Chalcones: Synthesis and Evaluation of Their Antifungal and Antimycobacterial Activity
Previous Article in Journal
Development of New 1,3-Diazaphenoxazine Derivatives (ThioG-Grasp) to Covalently Capture 8-Thioguanosine
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(1), 1088-1103; doi:10.3390/molecules20011088

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

1
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
2
Department of Fundamental Science, Beijing University of Agriculture, Beijing 102206, China
3
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 Synthesis)
View Full-Text   |   Download PDF [717 KB, uploaded 12 January 2015]   |  

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

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top