Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine

Abstract

. 2015. Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine. Can. J. Plant Sci. 95: 897Á903. The protective effects of herbicide safeners, including 3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine (R-28725), 3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (Racemate), and its two enantiomers (R)-3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (R-enantiomer) and (S)-3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (S-enantiomer), on reducing the phytotoxicity of chlorimuronethyl to maize were investigated. Soaking the seeds in safeners increased the endogenous glutathione (GSH) content and glutathione-S-transferase (GST) activity of maize. When induced by R-enantiomer, the GST activity in vivo and in vitro increased 180 and 192% compared with control, respectively. R-28725 and R-enantiomer also increased the acetolactate synthase (ALS) activity inhibited by chlorimuron-ethyl from 45 to 100 and 97% compared with the control, respectively. The kinetic parameter V max of GST in the maize treated with R-28725 and R-enantiomer increased by 103 and 92%, respectively, compared with the control. Our results suggest that R-28725 and R-enantiomer could significantly improve the GSH content, GST activity, and ALS activity of maize. Overall, maize could be protected from the injury caused by chlorimuron-ethyl.Key words: Herbicide injury, safener, 3-dichloroacetyl oxazolidine Zhao, L.-X., Qu, H.-T., Fu, Y., Gao, S. et Ye, F. 2015. Atte´nuation des dommages re´sultant du chlorimuron Á e´thyle chez le maı¨s traite´avec le phytoprotecteur 3-dichloroace´tyl oxazolidine. Can. J. Plant Sci. 95: 897Á903. Les auteurs ont examineć omment divers phytoprotecteurs, notamment la 3-dichloroace´tyl-2,2-dime´thyl-1,3-oxazolidine (R-28725), la 3-dichloroace´tyl-2, 2-dime´thyl-4-e´thyl-1,3-oxazolidine (Racemate) et leurs isome`res optiques (R)-3-dichloroace´tyl-2,2-dime´thyl-4-e´thyl-1,3-oxazolidine (isome`re optique R) et (S)-3-dichloroace´tyl-2,2-dime´thyl-4-e´thyl-1,3-oxazolidine (isome`re optique S), atte´nuent la toxicite´du chlorimuronÁe´thyle pour le maı¨s. Tremper les semences dans le phytoprotecteur augmente la concentration de glutathion endoge`ne (GSH) et l'activite´de la glutathion-S-transfe´rase (GST) du maı¨s. L'isome`re optique R augmente respectivement l'activite´in vivo et in vitro de la GST de 180 % et de 192 % comparativement aux te´moins. Le R-28725 et son isome`re optique R accroissent aussi l'activite´de l'ace´tolactate synthe´tase (ALS) inhibe´e par le chlorimuronÁe´thyle de 45 % a`100 % et de 97 %, respectivement, par rapport aux te´moins. Chez le maı¨s traite´avec du R-28725 et son isome`re optique R, le parame`tre cine´tique V max de la GST augmente respectivement de 103 % e de 92 % comparativement aux te´moins. Ces re´sultats donnent a`penser que le R-28725 et son isome`re optique R pourraient sensiblement augmenter la teneur en GSH, l'activite´de la GST et l'activite´de l'ALS chez le maı¨s. Dans l'ensemble, le maı¨s serait ainsi prote´ge´contre les do...

Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

“…According to our previous research on the biological activity of herbicide safeners [ 9 ], the residual concentration of chlorimuron-ethyl in soil was determined as 24 μg/kg. Before the tests, a preliminary screening was carried out to determine the best concentration of the title compounds, and Compound 4a was selected for the preliminary screening.…”

“…In order to reduce the injury, various methods have been reported, including restricted use of long residual herbicides, developing new herbicides and so on [ 8 ]. In addition to these methods, herbicide safeners, a class of agrochemicals that can reduce the negative effects of a herbicide on crops, have been commercialized [ 9 , 10 ].…”

“…As a mature safener, R-28725 (2,2-dichloro-1-(2,2-dimethyloxazolidin-3-yl)ethan-1-one) shows good safener biological activity [ 9 ], and thiazolidine may possess similar chemical properties to R-28725 due to bioisosterism [ 16 ]. Recently, researchers reported some thiazolidine compounds with favorable biological activities in protecting the maize from herbicide phytotoxicity [ 11 ].…”

Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide

“…However, when used under field conditions, herbicides often exhibit a negative effect on crop growth and yield, including corn, cereal, and rice [1][2][3][4][5][6][7]. In order to protect crops from potential injuries caused by herbicides, the use of herbicide safeners is the most straightforward and cost-effective method [8,9].…”

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

“…Studies indicated that some 3-dichloroacetylsubstituted oxazolidines with a chiral center often have different biological activities (Sriharsha & Shashikanth 2006;Zhao et al 2015). One of the most widely used dichloroacetamide safeners in maize was 3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine (R-29148).…”