The safener effect of chiral derivatives of 3-dichloroacetyl oxazolidine against haloxyfop-P-methyl-induced toxicity in maize

Fei, Ye; Cao, Hai-Feng; Fu, Ying; Zhao, Li‐Xia; Gao, Shuang

doi:10.13080/z-a.2016.103.004

Cited by 8 publications

(10 citation statements)

References 21 publications

(26 reference statements)

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“…In summary, the R -isomer can improve the GSH content as well as the activity of GST in maize seedlings so as to promote the conjugation of glutathione with chlorsulfuron and then protect maize from injury caused by sulfonylurea herbicides. The GST activity toward CDNB was previously reported to increase significantly after treatment with a safener compared with treatment with chlorsulfuron [35]. Similarly, our results indicate that the R -isomer changed the kinetic parameters V max and K M obviously, while the other two safeners led to relatively small changes.…”

Section: Discussionsupporting

confidence: 80%

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

et al. 2019

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Herbicide safeners selectively protect crops from herbicide injury while maintaining the herbicidal effect on the target weed. To some extent, the detoxification of herbicides is related to the effect of herbicide safeners on the level and activity of herbicide target enzymes. In this work, the expression of the detoxifying enzyme glutathione S-transferase (GST) and antioxidant enzyme activities in maize seedlings were studied in the presence of three potential herbicide safeners: 3-dichloroacetyl oxazolidine and its two optical isomers. Further, the protective effect of chiral herbicide safeners on detoxifying chlorsulfuron in maize was evaluated. All safeners increased the expression levels of herbicide detoxifying enzymes, including GST, catalase (CAT), and peroxidase (POD) to reduce sulfonylurea herbicide phytotoxicity in maize seedlings. Our results indicate that the R-isomer of 3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine can induce glutathione (GSH) production, GST activity, and the ability of GST to react with the substrate 1-chloro-2,4-dinitrobenzene (CDNB) in maize, meaning that the R-isomer can protect maize from damage by chlorsulfuron. Information about antioxidative enzyme activity was obtained to determine the role of chiral safeners in overcoming the oxidative stress in maize attributed to herbicides. The interaction of safeners and active target sites of acetolactate synthase (ALS) was demonstrated by molecular docking modeling, which indicated that both isomers could form a good interaction with ALS. Our findings suggest that the detoxification mechanism of chiral safeners might involve the induction of the activity of herbicide detoxifying enzymes as well as the completion of the target active site between the safener and chlorsulfuron.

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Section: Discussionsupporting

confidence: 80%

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

et al. 2019

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“…The chlorophyll content of plant leaves directly affects photosynthesis associated with plant growth [39]. A positive correlation between growth level and recovery of root length, recovery of plant weight and chlorophyll content has been observed in previous research [40]. As seen from Table 2, it was observed that compounds 5 showed different recoveries of wheat growth.…”

Section: Resultsmentioning

confidence: 68%

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

et al. 2019

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The dominance of safener can unite with herbicides acquiring the efficient protection of crop and qualifying control of weeds in agricultural fields. In order to solve the crop toxicity problem and exploit the novel potential safener for fenoxaprop-P-ethyl herbicide, a series of trichloromethyl dichlorobenzene triazole derivatives were designed and synthesized by the principle of active subunit combination. A total of 21 novel substituted trichloromethyl dichlorobenzene triazole compounds were synthesized by substituted aminophenol and amino alcohol derivatives as the starting materials, using cyclization and acylation. All the compounds were unambiguously characterized by IR, 1H-NMR, 13C-NMR, and HRMS. A greenhouse bioassay indicated that most of the title compounds could protect wheat from injury caused by fenoxaprop-P-ethyl at varying degrees, in which compound 5o exhibited excellent safener activity at a concentration of 10 μmol/L and was superior to the commercialized compound fenchlorazole. A structure–activity relationship for the novel compounds was determined, which demonstrated that those compounds containing benzoxazine groups showed better activity than that of oxazole-substituted compounds. Introducing a benzoxazine fragment and electron-donating group to specific positions could improve or maintain the safener activity for wheat against attack by the herbicide fenoxaprop-P-ethyl. A molecular docking model suggested that a potential mechanism between 5o and fenoxaprop-P-ethyl is associated with the detoxication of the herbicide. Results from the present work revealed that compound 5o exhibited good crop safener activities toward wheat and could be a promising candidate structure for further research on wheat protection.

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“…Overall, the R-isomer could protect maize from chloroacetanilide herbicide injury with enhanced GSH content and stimulated GST activity to promote glutathione conjugation with acetochlor in the maize seedlings. Compared with treated by acetochlor, dynamics of GST activity toward CDNB in safener-treatment increased significantly (Ye et al 2016). The data showed that the R-isomer significantly altered the kinetic parameter V max and K M .…”

Section: Pod and Cat Activitymentioning

confidence: 93%

“…It was found that the ability of safeners to protect maize from herbicide damage was related to the induction of glutathione-s-transferase activity (Fu et al 2011;Li et al 2017). Moreover, the researches had suggested that the detoxification ability of safener was involved in the level of glutathione conjugation in plant (Jo et al 2011;Ye et al 2016). However, the effects of chloroacetanilide safeners on the herbicide detoxification pathway were rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Effects of Chiral 3-Dichloroacetyl Oxazolidine on Glutathione S-Transferase and Antioxidant Enzymes Activity in Maize Treated with Acetochlor

Cao

Chen

et al. 2018

Tarım Bilimleri Dergisi

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The objective of this paper was to investigate the protective effect of three potential herbicide safeners (3-dichloroacetyl oxazolidine and its two optical isomers) on detoxifying to chloroacetanilide herbicide acetochlor in maize. In this study, physiological and biochemical tests were conducted under laboratory condition in 2015. All safeners increased the expression levels of herbicide detoxifying enzymes, including glutathione S-transferases (GST), catalase (CAT) and peroxidase (POD) to reduce chloroacetanilide herbicide phytotoxicity in maize seedlings. Our results suggest that the R-isomer of R-29148 can induce glutathione (GSH) expression, GST activity, and affinity for the 1-chloro-2,4-dinitrobenzene (CDNB) substrate in maize, which can protect maize from injury by chloroacetanilide herbicide acetochlor. Further information on the chiral safener role in antioxidative enzymes activation was obtained from CAT and POD activity to overcome oxidative stress caused by the herbicide.

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The safener effect of chiral derivatives of 3-dichloroacetyl oxazolidine against haloxyfop-P-methyl-induced toxicity in maize

Cited by 8 publications

References 21 publications

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

Protective Responses Induced by Chiral 3-Dichloroacetyl Oxazolidine Safeners in Maize (Zea mays L.) and the Detoxification Mechanism

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

Effects of Chiral 3-Dichloroacetyl Oxazolidine on Glutathione S-Transferase and Antioxidant Enzymes Activity in Maize Treated with Acetochlor

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