Hydrolysis of 3′,4′‐dichloropropionanilide by plant aryl acylamidases

Hoagland, Robert E.; Graf, George; Handel, E. D.

doi:10.1111/j.1365-3180.1974.tb01077.x

Cited by 26 publications

(13 citation statements)

References 14 publications

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“…in rice crops.1,2 The basis of selectivity between propanil-susceptible biotypes of Echinochloa colona (L.) Link and resistant rice has been established as the di †erential metabolism of this herbicide3,4 whereby propanil is Ðrstly converted to 3,4-dichloroaniline via a reaction catalysed by an aryl acylamidase. 5,6 Further metabolism of propanil is thought to involve glucosylation7,8 followed by incorporation into lignin9 and/or pectin cell wall polymers. 10 Extensive use of propanil has resulted in the selection of resistant biotypes of E. colona11 which has become a major problem weed in rice crops.…”

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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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 selectivity of propanil in rice crops is caused by differences in herbicide metabolism by the enzyme aryl acylamidase, which is present in both rice and Echinochloa spp. However, its activity is 60‐fold greater in rice than in grass weeds (Bowling & Hudgins, 1966; Frear & Still, 1968; Hoagland et al ., 1974; Pothuluri et al ., 1991). Fluorescence emission of chlorophyll has been used as an indirect measurement of the inhibitory effect of herbicides on photosynthesis.…”

Section: Introductionmentioning

confidence: 99%

Propanil activity, uptake and metabolism in resistant Echinochloa spp. biotypes

López-Martínez

Gonzalez-Gutierrez

2001

Weed Research

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Field resistance of Echinochloa spp. to propanil has been previously reported in Costa Rica, Colombia and Arkansas (USA). In this study, the mechanism of resistance was investigated in three resistant (R) and three susceptible (S) biotypes. The shoot fresh weight reduction in pot‐grown plants from a post‐emergence spray of propanil at 2.44 kg a.i. ha−1 on biotypes R/S from Costa Rica, Colombia and Arkansas was 35/98%, 25/79% and 20/82% respectively. In vitro chlorophyll fluorescence data from leaf tissue incubated in propanil showed that photosynthesis was inhibited in all biotypes, indicating that the propanil‐binding site and enzyme were not altered. After transfer to herbicide‐free solution, photosynthesis recovered only in resistant biotypes, indicating that the mechanism of resistance was caused by enhanced metabolism of the herbicide. Simultaneous treatment with fenitrothion, an aryl acylamidase inhibitor, prevented the recovery of photosynthesis in leaf tissue in two resistant biotypes. In contrast, the cytochrome P450 mono‐oxygenase inhibitor, 1‐aminobenzotriazole, did not prevent recovery from propanil in leaf tissue. Application of 14C‐propanil to the second leaf of intact Echinochloa plants showed that c. 90% of the radioactivity remained in the treated leaf for up to 72 h after application. No major differences in translocation between R and S biotype plants were found. TLC analysis of tissue extracts from the treated leaves showed substantially less radioactivity associated with propanil, present after 72 h in rice or in the three R biotypes, compared with S biotypes.

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“…Two replicates of 3 ml aliquots were taken from each cylinder and the concentration of 3,4-DCA was determined by the spectrophotometric method (Hoagland et al, 1974) First, 0.5 ml of a freshly prepared 1% solution of ΝaNO 2 was added to the aliquot with immediate mixing. After 10 min, 1.0 ml of a 10% solution of H 3 NO 3 S, followed by 1.0 ml MeOH was added to the aliquot with immediate mixing.…”

Section: Quantitative Determination Of 34-dca Plant Uptakementioning

confidence: 99%

A study of the role of micrometeorological conditions on uptake of 3,4-dichloroaniline in maize

Droulia

Odos²

2013

Global NEST Journal

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<p>3,4-dichloroaniline (3,4-DCA) is a hardly biodegradable and hydrolysable compound, characterized as a persistent pollutant for water, soil and sediment and highly toxic for living organisms. In this work, the impact of different micrometeorological conditions on uptake of 3,4-DCA was investigated in maize (Zea mays L.) plants grown hydroponically. For this purpose, seedlings of a uniform vigor were developed in appropriate nutrient solution supplied with an initial amount of 3,4-DCA (growth solution) under controlled high light (HL) and low light intensity (LL) conditions and under high (HH) and low relative humidity (LH) conditions in the combinations of HL/HH, LL/HH and HL/LH. Plants grown under HL/LH were replenished with the initial amount of 3,4-DCA after 48 h from the application of the growth solution (AGS). The measurements which took place were related to the uptake of 3,4-DCA and of growth solution by plants. Also, the fresh weight of plants was measured. Results showed that maize was capable of removing noticeably high amounts of 3,4-DCA (up to three quarters of the initial amount) from the growth solution after completion of the first 24 h period from AGS, irrespective of micrometeorological conditions. It was also demonstrated that almost the whole available amount of 3,4-DCA was removed from the growth solution after a 48 h period from AGS under HL/LH. Plants under these conditions removed a significantly higher volume of growth solution compared to the HH conditions, irrespective of measurement time. The significant increase of the 3,4-DCA uptake (almost the whole available amount) by maize plants which were replenished with this compound under LH compared to HH, indicated a considerable capability of these plants to remove high concentrations of 3,4-DCA from the growth solution after 72 h from AGS. The fresh weight of maize plants under the examined micrometeorological conditions did not change significantly in the majority of the cases, as regards to different micrometeorological conditions. On the contrary, this plant parameter was significantly higher in 3rd compared to 1st measurement day in all examined conditions. The increase of 3,4-DCA uptake rates by maize plants grown under low relative humidity conditions, 72 hrs from AGS, could be associated with the expected acceleration of the plants transpiration rates and with the plant growth rate, as expressed by the fresh weight, as in these conditions plants remove considerably high volume of growth solution. The information obtained from the aforementioned results on plant uptake of 3,4-DCA in maize plants could be a first step in designing suitable management practices such as phytoremediation strategies which might reduce environmental pollution.</p>

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Hydrolysis of 3′,4′‐dichloropropionanilide by plant aryl acylamidases

Cited by 26 publications

References 14 publications

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

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

Propanil activity, uptake and metabolism in resistant Echinochloa spp. biotypes

A study of the role of micrometeorological conditions on uptake of 3,4-dichloroaniline in maize

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