Mechanism of selective action of 3',4'-dichloropropionanilide.

doi:10.1104/PP.43.8.1291

Paper

Mechanism of selective action of 3',4'-dichloropropionanilide.

Published Aug 1, 1968 · R. Y. Yih, D. H. McRae, H. F. Wilson

Plant physiology

Q1 SJR score

66

Citations

2

Influential Citations

Full textSemantic Scholar

Abstract

Studies have been carried out to determine the basis for the unique postemergence selective action of the rice herbicide, 3',4'-dichloropropionanilide (DPA), which controls a wide variety of weed species including barnyardgrasses. Absorption studies have shown that both rice (Oryza sativa, L.) and barnyardgrass (Echinochloa crusgalli, L.) foliage absorb DPA readily and equally and, consequently, morphological differences cannot account for its unique selective action. Through the use of uniformly (14)C ring labeled and carbonyl labeled DPA in short-term studies (1-3 days), it has been found that rice and barnyardgrass leaves hydrolyze DPA to 3,4-dichloroaniline (DCA). It is further shown that this is not a direct 1-step hydrolysis, but rather an oxidative metabolism of DPA to 3',4'-dichlorolactanilide (DLA) followed by hydrolysis to DCA and lactic acid. In rice, DLA is a transient intermediate and not isolatable under normal conditions, whereas DLA accumulates in barnyardgrass and is readily isolated. The oxidative metabolism of DPA is rapid in rice but slow in barnyardgrass. Thus, DPA is detoxified rapidly in rice, but accumulates in barnyardgrass to lethal proportions and this difference is proposed as the primary basis for the selective action of DPA.Additional evidence for this mechanism comes from studies on the interaction of certain insecticides with DPA. It is known that the tolerance of rice and other crops to DPA can be completely eliminated when an insecticide such as carbaryl is present with the herbicide in the crop. Under these conditions, it has been found that DLA accumulates in the rice as it does in DPA treated barnyardgrass.

Study Snapshot

The selective action of 3',4'-dichloropropionanilide (DPA) in controlling weeds is primarily based on the rapid detoxification of DPA in rice and the accumulation of DLA in barnyardgrass, which leads to lethal concentrations.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Mechanism of selective action of 3',4'-dichloropropionanilide.

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References

Metabolism of 3',4'-Dichloropropionanilide: 3,4-Dichloroaniline-Lignin Complex in Rice Plants

Rice plants metabolize 3',4'-dichloropropionanilide to 3,4-dichloroaniline, which is mainly bound to lignin, resulting in a complex with carbohydrates.

Metabolism of 3',4'-Dichloropropionanilide: 3,4-Dichloroaniline-Lignin Complex in Rice Plants

Rice plants metabolize 3',4'-dichloropropionanilide to 3,4-dichloroaniline, which is mainly bound to lignin, resulting in a complex with carbohydrates.

Metabolism of 3,4-Dichloropropionanifide in Plants: The Metabolic Fate of the 3,4-Dichloroaniline Moiety

Propanil is metabolized in rice plants, with complexed aniline metabolites accounting for only 10% of the total propanil administered after 14 days.

Enzyme Detoxication of 3′,4′-Dichloropropionanilide in Rice and Barnyard Grass, a Factor in Herbicide Selectivity

3′,4′-dichloropropionanilide selectively destroys barnyard grass in rice fields, with enzyme detoxication playing a key role in its selectiveness.

An acylamidase in mammalian liver hydrolyzing the herbicide 3,4-dichloropropionanilide

Liver acylamidase hydrolyzes the herbicide STAM, which has low toxicity and is found in rats, rabbits, mice, and dogs, with no significant effect on its activity or toxicity.

Citations

Multiple Herbicide-Resistant Junglerice (Echinochloa colona): Identification of Genes Potentially Involved in Resistance through Differential Gene Expression Analysis

Multiple herbicide-resistant junglerice plants show upregulation of certain genes, suggesting potential resistance mechanisms.

Biochemical and Molecular Knowledge about Developing Herbicide-Resistant Weeds

Herbicide resistance in weeds is a useful tool for weed scientists to control and manage weeds, and genetic engineering can be used to produce herbicide-resistant crops.

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

Herbicide-resistant weeds in rice in the Philippines have evolved due to continuous use of 2,4-D, butachlor, and propanil, and farmers are shifting to different modes of action and manual weeding to prevent resistance.

Uptake and decomposition of the herbicide propanil in the plant Bidens pilosa L. dominating in the Yangtze Three Gorges Reservoir (TGR), China

Propanil residues in Bidens pilosa plants can potentially enter the aquatic environment after plant death and submergence, potentially impacting aquatic organisms.

A psbA mutation (Val219 to Ile) causes resistance to propanil and increased susceptibility to bentazon in Cyperus difformis.

The D1 Val219 Ile modification in Cyperus difformis causes resistance to propanil and other herbicides but increased susceptibility to bentazon, suggesting that tank mixing of these two compounds can effectively control both propanil-resistant and susceptible plants.