Enantioselective effects of chiral amide herbicides napropamide, acetochlor and propisochlor: The more efficient R-enantiomer and its environmental friendly

Xie, Jianhua; Zhao, Lu; Liu, Kai; Guo, Fei; Liu, Weiping

doi:10.1016/j.scitotenv.2018.01.140

Cited by 48 publications

(22 citation statements)

References 32 publications

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“…Liu et al, in their studies on chiral herbicides, concluded that the reactions between chlorine atoms and weed (Echinochloa crusgalli) proteins were characterized by the biological stereoselectivity. 39 In previously mentioned studies, it was observed that the (R)-enantiomers of napropamide, acetochlor and propisochlor had a stronger herbicidal effect than the (S)-enantiomers. The same research group studied enantioselective herbicidal properties of metolachlor, where, as in our research, it was shown that (S)-enantiomers exhibited stronger herbicidal properties than (R)-enantiomers.…”

Section: Herbicidal Activitymentioning

confidence: 96%

“…On the other hand, the reverse dependence has been reported for green algae S. obliquus in the case of (S)enantiomers of metolachlor and diclofop-methyl being more toxic. 38 In the case of M. aeruginosa, studies on napropamide, acetochlor and propisochlor, 39 as well as metolachlor 40 showed greater toxicity of the (S)-enantiomers than that of the (R)-enantiomers, based on the EC 20 values. Based on these literature data, it cannot be stated that enantioselective toxicity depends mainly on the type of the species investigated but rather it is related to a specific chemical structure of the herbicide and its interaction with a chiral biological environment.…”

Section: Microtox® Testmentioning

confidence: 99%

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The need to change the approach to the safe use of herbicides by developing chiral and environmentally friendly formulations: a series of enantioselective (R)- and (S)-phenylethylammonium chloroacetates

et al. 2022

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Section: Herbicidal Activitymentioning

confidence: 96%

Section: Microtox® Testmentioning

confidence: 99%

The need to change the approach to the safe use of herbicides by developing chiral and environmentally friendly formulations: a series of enantioselective (R)- and (S)-phenylethylammonium chloroacetates

et al. 2022

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“…Normally, biological systems exist exclusively in one enantiomeric form, so that they will interact differently with the two enantiomers of active compounds [35,36]. Numerous herbicides have chiral structures, and the two enantiomers have different actions against target weeds [37][38][39][40][41]. Therefore, we studied the different herbicidal effects of isomers of common amino acids (Figure 1), together with their racemic mixtures, on representative monocot and dicot plants.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective and Synergistic Herbicidal Activities of Common Amino Acids Against Amaranthus tricolor and Echinochloa crus-galli

2021

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Amino acids have a wide range of biological activities, which usually rely on the stereoisomer presented. In this study, glycine and 21 common α-amino acids were investigated for their herbicidal property against Chinese amaranth (Amaranthus tricolor L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). Both d- and l-isomers, as well as a racemic mixture, were tested and found that most compounds barely inhibited germination but moderately suppressed seedling growth. Various ratios of d:l-mixture were studied and synergy between enantiomers was found. For Chinese amaranth, the most toxic d:l-mixtures were at 3:7 (for glutamine), 8:2 (for methionine), and 5:5 (for tryptophan). For barnyard grass, rac-glutamine was more toxic than the pure forms; however, d-tryptophan exhibited greater activity than racemate and l-isomer, indicating the sign of enantioselective toxicity. The mode of action was unclear, but d-tryptophan caused bleaching of leaves, indicating pigment synthesis of the grass was inhibited. The results highlighted the enantioselective and synergistic toxicity of some amino acids, which relied upon plant species, chemical structures, and concentrations. Overall, our finding clarifies the effect of stereoisomers, and provides a chemical clue of amino acid herbicides, which may be useful in the development of herbicides from natural substances.

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“…For example, the effects of chiral pesticides have been widely studied (e.g. Qu et al, 2014;Xie et al, 2018), but less is known about the ecotoxicity of pharmaceutical enantiomers, with most of the research to date focusing on β-blockers, such as propranolol, and the antidepressant fluoxetine (Sanganyado et al, 2017). For example, Sun et al (2014) observed no enantiospecific differences in heart rate, hatching rate and mortality in zebrafish embryos after exposure to the (R)and (S)-enantiomers of propranolol and metoprolol.…”

Section: Introductionmentioning

confidence: 99%

Evaluating the enantiospecific differences of non-steroidal anti-inflammatory drugs (NSAIDs) using an ecotoxicity bioassay test battery

Neale

Branch

Khan

et al. 2019

Science of The Total Environment

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Wastewater treatment plants are a major pathway for pharmaceuticals to the aquatic environment. Many pharmaceuticals, including non-steroidal anti-inflammatory drugs (NSAIDs), are chiral chemicals and the biological activity of their enantiomers can differ. Few studies have assessed the effects of different NSAID enantiomers on non-target organisms. However, this information is important for environmental risk assessment to ensure that the effects of more potent enantiomers are not overlooked. In the current study, enantiomers of naproxen, ibuprofen, ketoprofen and flurbiprofen were evaluated in bioassays with bacteria, algae and fish cells. All enantiomers induced bacterial toxicity, with (R)-naproxen more toxic than (S)-naproxen (EC50 0.75 vs 0.93 mg/L) and (S)flurbiprofen more toxic than (R)-flurbiprofen (EC50 1.22 vs 2.13 mg/L). Both (R)-flurbiprofen and (S)-flurbiprofen induced photosystem II inhibition in green algae, with (R)-flurbiprofen having a greater effect in the assay after 24 h (EC10 6.92 vs 9.79 mg/L). Only the (R)-enantiomers of flurbiprofen and ketoprofen induced ethoxyresorufin-O-deethylase (EROD) activity in fish cells, while (S)-naproxen was 2.5 times more active than (R)-naproxen in the EROD assay. While enantiospecific differences were observed for all assays, the difference was less than an order of magnitude. This indicates that the risk of overlooking the effect of more potent NSAID enantiomers is minor for the studied test systems and supports the use of racemic (or single enantiomer) effect data for environmental risk assessment. However, further investigation of the (R)-enantiomer of commonly used NSAID ketoprofen is recommended as it was at least six times more potent in the EROD assay than the inactive (S)-ketoprofen.

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Enantioselective effects of chiral amide herbicides napropamide, acetochlor and propisochlor: The more efficient R-enantiomer and its environmental friendly

Cited by 48 publications

References 32 publications

The need to change the approach to the safe use of herbicides by developing chiral and environmentally friendly formulations: a series of enantioselective (R)- and (S)-phenylethylammonium chloroacetates

The need to change the approach to the safe use of herbicides by developing chiral and environmentally friendly formulations: a series of enantioselective (R)- and (S)-phenylethylammonium chloroacetates

Enantioselective and Synergistic Herbicidal Activities of Common Amino Acids Against Amaranthus tricolor and Echinochloa crus-galli

Evaluating the enantiospecific differences of non-steroidal anti-inflammatory drugs (NSAIDs) using an ecotoxicity bioassay test battery

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