Mechanism of Selective Action of 3′,4′-Dichloropropionanilide

Yih, Roy Y.; McRae, D. Harold; Wilson, Harold F.

doi:10.1104/pp.43.8.1291

Cited by 66 publications

(40 citation statements)

References 8 publications

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“…Although we did not positively identify these metabolites via structural analysis, other researchers studying propanil metabolism in rice using the pyridine ] n-butanol ] water solvent system10 have identiÐed metabolites with similar R f values as 3,4-dichlorophenyl-glucosylamine (R f \ 0É78) and a 3,4-dichlorophenyl-saccharide conjugate (R f \ 0É60). 10,12,13,21 It is likely that the metabolites recovered in our studies are the same conjugates, since they were present in both rice and propanil-resistant barnyardgrass, and similar values were obtained using R f these two solvent systems. These conclusions are supported by the higher level of non-extractable 14C in rice and propanil-resistant barnyardgrass.…”

Section: Laboratory Experimentssupporting

confidence: 70%

“…The propionate moiety is metabolized to carbon dioxide via b-oxidation11 and the DCA moiety is enzymatically conjugated with either glucose to form N- (3,4-dichlorophenyl)glucosylamine, or with other saccharides (glucose, xylose and fructose) to form DCAsaccharide conjugates.12,13 This hydrolytic pathway is the basis of the selectivity mechanism for barnyardgrass control in rice since only extremely low levels of aryl acylamidase are present in sensitive barnyardgrass, hence the absorbed herbicide is not sufficiently hydrolysed (detoxiÐed) to DCA. 10,11,14 Rice is not the only plant, however, that metabolizes propanil via aryl acylamidases. Aryl acylamidase activity has been found in over 30 plant species including red rice (Oryza sativa L.) (a conspeciÐc weed of common rice), tulip (T ulipa gesneriana L.), dandelion (T araxacum officinale Weber) and lettuce (L actuca sativa L.).15h19 Metabolism of propanil to DCA and propionic acid is also the selectivity mechanism for green foxtail (Setaria viridis (L) Beauv.)…”

Section: Introductionmentioning

confidence: 99%

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Resistance Mechanism of Propanil-Resistant Barnyardgrass: II. In-vivo Metabolism of the Propanil Molecule

1997

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Propanil-resistant barnyardgrass populations, previously veriÐed in Arkansas rice Ðelds and in greenhouse tests, were examined in the laboratory to ascertain if the resistance mechanism in this weed biotype was herbicide metabolism. Propanil-resistant barnyardgrass was controlled [95% in the greenhouse when carbaryl (an aryl acylamidase inhibitor) was applied two days prior to propanil. Laboratory studies with 14C-radiolabelled propanil indicated that the herbicide was hydrolysed in propanil-resistant barnyardgrass and rice to form 3,4-dichloroaniline, but no detectable hydrolysis occurred in susceptible barnyardgrass. Two additional polar metabolites were detected in propanil-resistant barnyardgrass and rice and tentatively identiÐed by thin layer chromatography. Overall, metabolites in the resistant barnyardgrass had values similar to those R f in rice, indicating similar metabolism for both species. These data, coupled with data from a previous report on the resistant biotype showing no di †erential absorption/translocation or molecular modiÐcation of the herbicide binding site in the resistant biotype, indicate that the resistance mechanism is metabolic degradation of propanil.

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Section: Laboratory Experimentssupporting

confidence: 70%

Section: Introductionmentioning

confidence: 99%

Resistance Mechanism of Propanil-Resistant Barnyardgrass: II. In-vivo Metabolism of the Propanil Molecule

1997

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“…Attempts to improve efficacy of propanil have included the use of carbamate and organophosphorus insecticides as synergists12h14 since these compounds are known to inhibit aryl acylamidase activity15 thereby enhancing the phytotoxicity of propanil by reducing its metabolism. 3,4,16,17 However, tolerance to propanil in E. colona increases with plant age, possibly due to an observed decrease in uptake of this herbicide. 18 Consequently, selective phytotoxicity of propanil based upon di †erences in aryl acylamidase-mediated metabolism is progressively reduced with plant age, suggesting that even propanilÈ insecticide mixtures would have limited use in the control of older E. colona plants.…”

Section: Introductionmentioning

confidence: 99%

Effect of Mono-oxygenase Inhibitors on Uptake, Metabolism and Phytotoxicity of Propanil in Resistant Biotypes of Jungle-Rice,Echinochloa Colona

et al. 1997

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: The e †ect of the mono-oxygenase inhibitors tridiphane, piperonyl butoxide and prochloraz on propanil uptake, metabolism and phytotoxicity was measured in a resistant (R) biotype of Echinochloa colona. The uptake of propanil was not signiÐcantly a †ected by any of the three mono-oxygenase inhibitors. The Ðrst metabolite of propanil metabolism, 3,4-dichloroaniline, was found to accumulate to higher levels in E. colona treated with each of the mono-oxygenase inhibitors mixed with formulated propanil, compared to propanil applied alone.Accumulation of further metabolites of propanil (glucosyl-3,4-dichloroaniline and bound products) was reduced in the presence of mono-oxygenase inhibitors, compared with propanil application alone. Leaf damage caused by a single drop of propanil compared to propanil ] mono-oxygenase inhibitor was used to assess the degree of propanil tolerance in E. colona biotypes. Leaf damage was signiÐcantly greater in propanil ] mono-oxygenase inhibitor treatments. No leaf damage was observed in mono-oxygenase inhibitor treatments alone at the concentrations used.Peroxidase activity was measured in crude extracts of the R-biotype of E. colona using 3,4-dichloroaniline as substrate, in the presence and absence of mono-oxygenase inhibitors and the speciÐc peroxidase inhibitor salicylhydroxamic acid. Peroxidase activity was inhibited by all three monooxygenase inhibitors at 10 kM and by salicylhydroxamic acid at 1 kM. Glucosyl-3,4-dichloroaniline was found not to be a substrate for peroxidase activity.These results suggest that the incorporation of 3,4-dichloroaniline into bound residues involves peroxidase activity which can be inhibited by mono-oxygenase inhibitors. When peroxidase activity is inhibited, the precursor metabolite 3,4-dichloroaniline accumulates, and propanil resistance in E. colona is reduced, possibly as a consequence of phytotoxicity of this metabolite and/or product inhibition of the Ðrst step in propanil metabolism, responsible for the formation of 3,4-dichloroaniline. Glasshouse trials have demonstrated that the application of mono-oxygenase inhibitors, (particularly tridiphane which is also known to inhibit glutathione transferase activity) with propanil o †ers a promising approach to the control of propanil resistant biotypes of Jungle-Rice.

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“…Unlike the other PSII inhibitors, such as the triazines, the mechanism of resistance to propanil is not target site resistance but metabolic resistance. Propanil has physiological selectivity between emerged rice and grasses due to the existence of an endogenous enzyme in tolerant rice that hydrolyzes propanil into non‐toxic metabolites (3,4‐dichloroaniline and propionic acid) and subsequent inactivation by conjugation of these metabolites with sugars or incorporation with lignin (Still ,; Yih et al ,). The enzyme, arylacylamidase (EC 3.5.1.a), is low, if not totally absent, in susceptible barnyardgrass and most grass weeds (Frear & Still ).…”

Section: Biology and Mechanisms Of Resistancementioning

confidence: 99%

Herbicide‐resistant weeds in the Philippines: Status and resistance mechanisms

Baltazar

2017

Weed Biology and Management

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Two major weeds in rice in the Philippines, Sphenochlea zeylanica Gaertn. and Echinochloa crus‐galli (L.) Beauv., are controlled with chemical and cultural methods. In the 1980s, after >10 years of continuous use of 2,4‐D, S. zeylanica evolved resistance to the chemical in those rice fields that had been treated with 2,4‐D once or twice every cropping season. In the 1990s, E. crus‐galli evolved resistance to butachlor and propanil in rice monocrop areas where both herbicides were used continuously for 7–9 years. Rice farmers continue to use 2,4‐D, butachlor and propanil extensively and are often unaware of herbicide resistance or the potential for cross‐resistance, its causes or its implications. In order to control herbicide‐resistant E. crus‐galli, farmers are shifting to locally available herbicides with different modes of action, such as bispyribac, an acetolactate synthase inhibitor, and cyhalofop, an acetyl coenzyme A carboxylase inhibitor. Follow‐up manual weeding or rotary weeding after herbicide spraying, a common farmers’ practice, removes the susceptible and resistant biotypes and could help to delay or prevent the evolution of resistance. Although the resistance mechanisms of both weeds are not determined yet, they could be related to enhanced degradation that is similar to the mechanisms that are shown by the resistant biotypes in other countries.

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Mechanism of Selective Action of 3′,4′-Dichloropropionanilide

Abstract: Abstract. Studies have been carried out to determine the basis for the unique postemergence selective action of the rice herbicide, 3',4'-dichloropropionanilide (DPA)

Cited by 66 publications

References 8 publications

Resistance Mechanism of Propanil-Resistant Barnyardgrass: II. In-vivo Metabolism of the Propanil Molecule

Resistance Mechanism of Propanil-Resistant Barnyardgrass: II. In-vivo Metabolism of the Propanil Molecule

Effect of Mono-oxygenase Inhibitors on Uptake, Metabolism and Phytotoxicity of Propanil in Resistant Biotypes of Jungle-Rice,Echinochloa Colona

Herbicide‐resistant weeds in the Philippines: Status and resistance mechanisms

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