Trifluralin

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Stephen B. Powles - One of the best experts on this subject based on the ideXlab platform.

  • loss of Trifluralin metabolic resistance in lolium rigidum plants exposed to prosulfocarb recurrent selection
    Pest Management Science, 2020
    Co-Authors: Roberto Busi, Stephen B. Powles, Danica E. Goggin, Christopher Preston, Andrea Onofri, Peter Boutsalis, Hugh J Beckie
    Abstract:

    BACKGROUND Resistance to the dinitroaniline herbicide Trifluralin in Lolium rigidum (annual ryegrass) often is mediated by the enhanced capacity to metabolize the herbicide to less toxic polar conjugates and/or by functionally recessive target-site mutations in α-tubulin. RESULTS In two L. rigidum populations possessing enhanced Trifluralin metabolism, resistance was largely reversed by recurrent selection with the thiocarbamate herbicide prosulfocarb (i.e. plant survival was two- to >20-fold lower). Their ability to metabolize Trifluralin was significantly decreased (by ≈2.3-fold) following recurrent prosulfocarb selection, to levels comparable to those observed in susceptible plants or when Trifluralin metabolism was inhibited by treatment with the insecticide phorate. CONCLUSIONS This study provides evidence that trait(s) enabling efficient Trifluralin metabolism in L. rigidum are purged from the population under prosulfocarb recurrent selection. The level of Trifluralin metabolism in vitro and its inhibition caused by phorate action on Trifluralin-metabolizing enzyme(s) is equivalent to the effect produced by prosulfocarb selection. The hypothetical link between the two phenomena is that the putative monooxygenase(s) conferring Trifluralin metabolic resistance also mediate the activation of prosulfocarb to its toxic sulfoxide. Thus, we speculate that survival to prosulfocarb via a lack of metabolic herbicide activation, and survival to Trifluralin conferred by enhanced herbicide metabolism, are mutually exclusive. These findings not only open up a new research direction in terms of the interaction between different herbicide resistance mechanisms in L. rigidum, but also offer strategies for immediate management of the population dynamics of metabolism-based resistance in the field. © 2020 Society of Chemical Industry.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum.
    Journal of agricultural and food chemistry, 2018
    Co-Authors: Jinyi Chen, Heping Han, Roberto Busi, Danica E. Goggin, Stephen B. Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detec...

  • novel α tubulin mutations conferring resistance to dinitroaniline herbicides in lolium rigidum
    Frontiers in Plant Science, 2018
    Co-Authors: Zhizhan Chu, Jinyi Chen, Heping Han, Alex Nyporko, Stephen B. Powles
    Abstract:

    The dinitroaniline herbicides (particularly Trifluralin) have been globally used in many crops for selective grass weed control. Consequently, Trifluralin resistance has been documented in several important crop weed species and has recently reached a level of concern in Australian Lolium rigidum populations. Here, we report novel mutations in the L. rigidum α-tubulin gene which confer resistance to Trifluralin and other dinitroaniline herbicides. Nucleotide mutations at the highly conserved codon Arg-243 resulted in amino acid substitutions of Met or Lys. Rice calli transformed with the mutant 243-Met or 243-Lys α-tubulin genes were 4- to 8-fold more resistant to Trifluralin and other dinitroaniline herbicides (e.g., ethalfluralin and pendimethalin) compared to calli transformed with the wild type α-tubulin gene from L. rigidum. Comprehensive modeling of molecular docking predicts that Arg-243 is close to the Trifluralin binding site on the α-tubulin surface and that replacement of Arg-243 by Met/Lys-243 results in a spatial shift of the Trifluralin binding domain, reduction of Trifluralin-tubulin contacts, and unfavorable interactions. The major effect of these substitutions is a significant rise of free interaction energy between α-tubulin and Trifluralin, as well as between Trifluralin and its whole molecular environment. These results demonstrate that the Arg-243 residue in α-tubulin is a determinant for Trifluralin sensitivity, and the novel Arg-243-Met/Lys mutations may confer Trifluralin resistance in L. rigidum.

Jinyi Chen - One of the best experts on this subject based on the ideXlab platform.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum.
    Journal of agricultural and food chemistry, 2018
    Co-Authors: Jinyi Chen, Heping Han, Roberto Busi, Danica E. Goggin, Stephen B. Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detec...

  • novel α tubulin mutations conferring resistance to dinitroaniline herbicides in lolium rigidum
    Frontiers in Plant Science, 2018
    Co-Authors: Zhizhan Chu, Jinyi Chen, Heping Han, Alex Nyporko, Stephen B. Powles
    Abstract:

    The dinitroaniline herbicides (particularly Trifluralin) have been globally used in many crops for selective grass weed control. Consequently, Trifluralin resistance has been documented in several important crop weed species and has recently reached a level of concern in Australian Lolium rigidum populations. Here, we report novel mutations in the L. rigidum α-tubulin gene which confer resistance to Trifluralin and other dinitroaniline herbicides. Nucleotide mutations at the highly conserved codon Arg-243 resulted in amino acid substitutions of Met or Lys. Rice calli transformed with the mutant 243-Met or 243-Lys α-tubulin genes were 4- to 8-fold more resistant to Trifluralin and other dinitroaniline herbicides (e.g., ethalfluralin and pendimethalin) compared to calli transformed with the wild type α-tubulin gene from L. rigidum. Comprehensive modeling of molecular docking predicts that Arg-243 is close to the Trifluralin binding site on the α-tubulin surface and that replacement of Arg-243 by Met/Lys-243 results in a spatial shift of the Trifluralin binding domain, reduction of Trifluralin-tubulin contacts, and unfavorable interactions. The major effect of these substitutions is a significant rise of free interaction energy between α-tubulin and Trifluralin, as well as between Trifluralin and its whole molecular environment. These results demonstrate that the Arg-243 residue in α-tubulin is a determinant for Trifluralin sensitivity, and the novel Arg-243-Met/Lys mutations may confer Trifluralin resistance in L. rigidum.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum
    2018
    Co-Authors: Jinyi Chen, Roberto Busi, Heping Han, Danica Goggin, Stephen Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detection, overcoming the difficulties of quantifying this highly volatile herbicide by chromatographic methods

Roberto Busi - One of the best experts on this subject based on the ideXlab platform.

  • loss of Trifluralin metabolic resistance in lolium rigidum plants exposed to prosulfocarb recurrent selection
    Pest Management Science, 2020
    Co-Authors: Roberto Busi, Stephen B. Powles, Danica E. Goggin, Christopher Preston, Andrea Onofri, Peter Boutsalis, Hugh J Beckie
    Abstract:

    BACKGROUND Resistance to the dinitroaniline herbicide Trifluralin in Lolium rigidum (annual ryegrass) often is mediated by the enhanced capacity to metabolize the herbicide to less toxic polar conjugates and/or by functionally recessive target-site mutations in α-tubulin. RESULTS In two L. rigidum populations possessing enhanced Trifluralin metabolism, resistance was largely reversed by recurrent selection with the thiocarbamate herbicide prosulfocarb (i.e. plant survival was two- to >20-fold lower). Their ability to metabolize Trifluralin was significantly decreased (by ≈2.3-fold) following recurrent prosulfocarb selection, to levels comparable to those observed in susceptible plants or when Trifluralin metabolism was inhibited by treatment with the insecticide phorate. CONCLUSIONS This study provides evidence that trait(s) enabling efficient Trifluralin metabolism in L. rigidum are purged from the population under prosulfocarb recurrent selection. The level of Trifluralin metabolism in vitro and its inhibition caused by phorate action on Trifluralin-metabolizing enzyme(s) is equivalent to the effect produced by prosulfocarb selection. The hypothetical link between the two phenomena is that the putative monooxygenase(s) conferring Trifluralin metabolic resistance also mediate the activation of prosulfocarb to its toxic sulfoxide. Thus, we speculate that survival to prosulfocarb via a lack of metabolic herbicide activation, and survival to Trifluralin conferred by enhanced herbicide metabolism, are mutually exclusive. These findings not only open up a new research direction in terms of the interaction between different herbicide resistance mechanisms in L. rigidum, but also offer strategies for immediate management of the population dynamics of metabolism-based resistance in the field. © 2020 Society of Chemical Industry.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum.
    Journal of agricultural and food chemistry, 2018
    Co-Authors: Jinyi Chen, Heping Han, Roberto Busi, Danica E. Goggin, Stephen B. Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detec...

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum
    2018
    Co-Authors: Jinyi Chen, Roberto Busi, Heping Han, Danica Goggin, Stephen Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detection, overcoming the difficulties of quantifying this highly volatile herbicide by chromatographic methods

Heping Han - One of the best experts on this subject based on the ideXlab platform.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum.
    Journal of agricultural and food chemistry, 2018
    Co-Authors: Jinyi Chen, Heping Han, Roberto Busi, Danica E. Goggin, Stephen B. Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detec...

  • novel α tubulin mutations conferring resistance to dinitroaniline herbicides in lolium rigidum
    Frontiers in Plant Science, 2018
    Co-Authors: Zhizhan Chu, Jinyi Chen, Heping Han, Alex Nyporko, Stephen B. Powles
    Abstract:

    The dinitroaniline herbicides (particularly Trifluralin) have been globally used in many crops for selective grass weed control. Consequently, Trifluralin resistance has been documented in several important crop weed species and has recently reached a level of concern in Australian Lolium rigidum populations. Here, we report novel mutations in the L. rigidum α-tubulin gene which confer resistance to Trifluralin and other dinitroaniline herbicides. Nucleotide mutations at the highly conserved codon Arg-243 resulted in amino acid substitutions of Met or Lys. Rice calli transformed with the mutant 243-Met or 243-Lys α-tubulin genes were 4- to 8-fold more resistant to Trifluralin and other dinitroaniline herbicides (e.g., ethalfluralin and pendimethalin) compared to calli transformed with the wild type α-tubulin gene from L. rigidum. Comprehensive modeling of molecular docking predicts that Arg-243 is close to the Trifluralin binding site on the α-tubulin surface and that replacement of Arg-243 by Met/Lys-243 results in a spatial shift of the Trifluralin binding domain, reduction of Trifluralin-tubulin contacts, and unfavorable interactions. The major effect of these substitutions is a significant rise of free interaction energy between α-tubulin and Trifluralin, as well as between Trifluralin and its whole molecular environment. These results demonstrate that the Arg-243 residue in α-tubulin is a determinant for Trifluralin sensitivity, and the novel Arg-243-Met/Lys mutations may confer Trifluralin resistance in L. rigidum.

  • Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum
    2018
    Co-Authors: Jinyi Chen, Roberto Busi, Heping Han, Danica Goggin, Stephen Powles
    Abstract:

    Resistance to the pre-emergence herbicide Trifluralin is increasing in Australian annual ryegrass (Lolium rigidum) populations. Three L. rigidum populations (R1, R2, and R3) collected from Australian grain fields were identified with Trifluralin resistance. Both target-site and nontarget-site resistance mechanisms were investigated. No target-site α-tubulin mutations were detected in populations R1 and R3, while an Arg-243-Lys mutation was found in R2. Compared with the three Trifluralin-susceptible populations, enhanced [14C]-Trifluralin metabolism, quantified by measuring the amount of [14C] label partitioning into the polar phase of a hexane:methanol system, was identified in all the three resistant populations. This is the first report of metabolic resistance to Trifluralin. Coevolution of target-site and nontarget-site resistance to Trifluralin is occurring, and metabolic resistance is not rare in L. rigidum populations in Australia. A method was established for Trifluralin metabolic resistance detection, overcoming the difficulties of quantifying this highly volatile herbicide by chromatographic methods

Hiroshi Matsumoto - One of the best experts on this subject based on the ideXlab platform.

  • Mutation of alpha-tubulin genes in Trifluralin-resistant water foxtail (Alopecurus aequalis)
    Pest management science, 2011
    Co-Authors: Saima Hashim, Asad Jan, Yukari Sunohara, Mayumi Hachinohe, Hideki Ohdan, Hiroshi Matsumoto
    Abstract:

    BACKGROUND: Trifluralin-resistant biotypes of water foxtail (Alopecurus aequalis) have been identified in wheat fields from northern Kyushu, Japan. Water foxtail is a winter-annual grassy weed, causing substantial crop losses. This study reports on mutation in α-tubulin (TUA) genes from water foxtail, the site of action of Trifluralin. RESULTS: Two Trifluralin-sensitive (S) Chikugo and Ukiha biotypes and four Trifluralin-resistant (R) Asakura-1, Asakura-2, Tamana and Tosu biotypes of water foxtail were used for herbicide resistance analysis. R biotypes showed 5.7–30.7-fold Trifluralin resistance compared with the S biotypes. No differences in the uptake and translocation of 14C-Trifluralin were observed between Chikugo (S) biotype and Asakura-1 (R) biotype. Most of the 14C detected in the plant material was in the root tissue, and no substantial increases were noted in shoot tissues. Comparative TUA sequence analysis revealed two independent single amino acid changes: change of Val into Phe at position 202 in TUA1 and change of Leu into Met at position 125 in TUA3 in Asakura-1 biotype. In the Tamana (R) biotype, two amino acid changes of Leu to Phe at position 136 and Val to Phe at position 202 were observed in the predicted amino acid sequence of TUA1, compared with Chikugo (S) biotype. CONCLUSION: The results provide preliminary molecular explanation for the resistance of water foxtail to Trifluralin, a phenomenon that has arisen as a result of repeated exposure to this class of herbicide. This is the first report of α-tubulin mutation in water foxtail and for any Alopecurus species reported in the literature. Copyright © 2011 Society of Chemical Industry