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Activity, toxicity, molecular docking, and environmental effects of three imidazolinone herbicides enantiomers

Xie, Jingqian and Zhao, Lu and Liu, Kai and Guo, Fangjie and Gao, Lidi and Liu, Weiping (2018) Activity, toxicity, molecular docking, and environmental effects of three imidazolinone herbicides enantiomers. Science of the Total Environment, 622-623 . pp. 594-602. ISSN 0048-9697. http://resolver.caltech.edu/CaltechAUTHORS:20171213-140836043

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Abstract

All imidazolinone (IMI) herbicides are chiral consisting of two enantiomers; however, studies on the enantioselectivities of their interactions are limited. This study is a systematic assessment of the enantiomers and racemates of IMI herbicides, including semi-preparation and determination of absolute configurations, stereoselective bioactivity toward target organisms (Echinochloa crus-galli and Microcystis aeruginosa), and toxicity toward Michigan Cancer Foundation-7 (MCF-7) cells. R-imidazolinones were found to be more active than S-IMIs in the inhibition of target organisms, and neither enantiomer had estrogenic activity. Moreover, the relationship between the molecular structures and the efficiency of target growth inhibition by the IMI herbicides was investigated. Molecular modeling provided the rational structural basis for the enantioselectivity of the acetohydroxyacid synthase (AHAS) activity of the IMIs. These findings encourage the application of enantiopure R-IMI herbicides to capitalize on their advantages over the racemates.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.scitotenv.2017.11.333DOIArticle
http://www.sciencedirect.com/science/article/pii/S0048969717333910PublisherArticle
ORCID:
AuthorORCID
Liu, Weiping0000-0002-1173-892X
Additional Information:© 2017 Elsevier B.V. Received 16 September 2017, Revised 28 November 2017, Accepted 28 November 2017, Available online 13 December 2017.
Subject Keywords:Chiral; Enantio-activity; Enantio-toxicity; Molecular docking
Record Number:CaltechAUTHORS:20171213-140836043
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20171213-140836043
Official Citation:Jingqian Xie, Lu Zhao, Kai Liu, Fangjie Guo, Lidi Gao, Weiping Liu, Activity, toxicity, molecular docking, and environmental effects of three imidazolinone herbicides enantiomers, Science of The Total Environment, Volumes 622–623, 1 May 2018, Pages 594-602, ISSN 0048-9697, https://doi.org/10.1016/j.scitotenv.2017.11.333. (https://www.sciencedirect.com/science/article/pii/S0048969717333910)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:83886
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Dec 2017 22:12
Last Modified:13 Dec 2017 22:12

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