A comparative investigation of the metabolism of the herbicide glufosinate in cell cultures of transgenic glufosinate-resistant and non-transgenic oilseed rape (<i>Brassica napus</i>) and corn (<i>Zea mays</i>)

Ruhland, Monika; Engelhardt, G.; Pawlizki, K.-H.

doi:10.1051/ebr:2002003

Cited by 13 publications

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“…The extraction procedure was repeated three times and the extracts were combined. Aqueous extracts were analysed for extractable 14 C‐radioactivity by scintillation counting and the 14 C‐activity of the non‐extractable residue was determined by combustion as described in a recent publication 5. Before further clean‐up, the volume of the extracts was reduced to 40 ml using rotary evaporation and freeze drying.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Metabolism studies of glufosinate, L ‐glufosinate and D ‐glufosinate have been performed up to now only with cell cultures of both non‐transgenic and transgenic plants of different species 5–7. Comparative investigation in cell cultures of non‐transgenic and transgenic oilseed rape and maize after separate application of glufosinate and its enantiomers showed that L ‐glufosinate was partly metabolised, whilst D ‐glufosinate was found to be stable 5. The main metabolite in non‐transgenic rape and maize cells was 4‐methylphosphinyl‐2‐oxo‐butanoic acid (PPO) together with small amounts of 3‐methylphosphinylpropionic acid (MPP), 4‐methylphosphinyl‐2‐hydroxybutanoic acid (MHB), 4‐methylphosphinylbutanoic acid (MPB) and 2‐methylphosphinylacetic acid (MPA).…”

Section: Introductionmentioning

confidence: 99%

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Distribution and metabolism of D/L‐, L‐ and D‐glufosinate in transgenic, glufosinate‐tolerant crops of maize (Zea mays L ssp mays) and oilseed rape (Brassica napus L var napus)

Ruhland

Engelhardt

Pawlizki

2004

Pest Management Science

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The aim of the present study was to determine whether post-emergence application of glufosinate to transgenic crops could lead to an increase in residues or to the formation of new, hitherto unknown metabolites. Transgenic oilseed rape and maize plants were treated separately with L-glufosinate, D-glufosinate or the racemic mixture. Whereas about 90% of the applied D-glufosinate was washed off by rain and only 5-6% was metabolised, 13-35% of the applied L-glufosinate remained in the form of metabolites and unchanged herbicide in both transgenic maize and oilseed rape. The main metabolite was N-acetyl-L-glufosinate with total residues of 91% in oilseed rape and 67% in maize, together with small amounts, of 5% in oilseed rape and 28% in maize, of different methylphosphinyl fatty acids. These metabolites were probably formed from L-glufosinate by deamination and subsequent decarboxylation. The residues were distributed in all fractions of the plants, with the highest contents in treated leaves and the lowest in the grains (0.07-0.3% in maize and 0.4-0.6% in oilseed rape). There was no indication of an accumulation of total residues or of residue levels above the official tolerances for glufosinate.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Distribution and metabolism of D/L‐, L‐ and D‐glufosinate in transgenic, glufosinate‐tolerant crops of maize (Zea mays L ssp mays) and oilseed rape (Brassica napus L var napus)

Ruhland

Engelhardt

Pawlizki

2004

Pest Management Science

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“…Although DAAOs are found in many microorganisms and animals (Curti et al, 1992) plants do not contain DAAOs at all; TBLASTX searches of RtDAAO against plant DNA databases that include the full-genome sequences of rice and Arabidopsis (Goff et al, 2002; EMBL release version 102; January 11th 2010) fail to find high scoring matches. Neither do plants appear to contain any other activity capable of metabolizing D-glufosinate (Ruhland et al, 2002).…”

Section: Discussionmentioning

confidence: 97%

d‐glufosinate as a male sterility agent for hybrid seed production

Hawkes

Pline-Srnić

Dale

et al. 2011

Plant Biotechnology Journal

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SummaryA chemical male sterility system based on anther-localized conversion of the inactive D-enantiomer of the herbicide, glufosinate (2-amino-4-(methylphosphinyl)-butanoate) to the phytotoxic L is described. Highly pure D-glufosinate was isolated in >98% enantiomeric excess from the racemate via fermentation with a strain of Escherichia with anther expression of a modified DAAO promises to provide a cost-effective conditional chemical male sterility system with the characteristics necessary for practical F 1 hybrid seed production.

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“…In addition, the different biotransformations of rac -glufosinate, l -glufosinate, and d -glufosinate reportedly depend on the plant species. rac -Glufosinate and l -glufosinate were metabolized in non-transgenic and transgenic plant cell cultures, whereas d -glufosinate was not metabolized [27]. However, most chiral pesticides are released into the environment in their racemic forms as equimolar mixtures of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective hydrolyzation and photolyzation of dufulin in water

Zhang

Zhu

et al. 2013

Chemistry Central Journal

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BackgroundDufulin is a novel, highly effective antiviral agent that activatives systemic acquired resistance of plants. This compound is widely used in China to prevent and control viral diseases in tobacco, vegetable and rice. Dufulin can treat plants infected by the tobacco mosaic virus and the cucumber mosaic virus. However, the achiral analysis and residue determination of dufulin remain underdeveloped because of its high enantioselectivity rates and high control costs. The enantioselectivity of an antiviral compound is an important factor that should be considered when studying the effect of chiral pesticides on the environment. The enantioselective degradation of dufulin in water remains an important objective in pesticide science.ResultsThe configuration of dufulin enantiomers was determined in this study based on its circular dichroism spectra. The S-(+)-dufulin and R-(−)-dufulin enantiomers were separated and identified using an amylose tris-(3,5-dimethylphenylcarbamate) chiral column by normal phase high-performance liquid chromatography. The degradation of the rac-dufulin racemate and its separate enantiomers complied with first-order reaction kinetics and demonstrated acceptable linearity. The enantioselective photolysis of rac-dufulin allowed for the faster degradation of R-(−)-dufulin, as compared with S-(+)-dufulin. However, S-(+)-dufulin was hydrolyzed faster than its antipode.ConclusionThe photolysation and hydrolyzation of dufulin in water samples normally complied with the first-order kinetics and demonstrated acceptable linearity (R2>0.66). A preferential photolysation of the R-(−)-enantiomer was observed in water samples. Moreover, the S-(+)-enantiomer was hydrolyzed faster than its antipode.

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A comparative investigation of the metabolism of the herbicide glufosinate in cell cultures of transgenic glufosinate-resistant and non-transgenic oilseed rape (Brassica napus) and corn (Zea mays)

Cited by 13 publications

References 12 publications

Distribution and metabolism of D/L‐, L‐ and D‐glufosinate in transgenic, glufosinate‐tolerant crops of maize (Zea mays L ssp mays) and oilseed rape (Brassica napus L var napus)

Distribution and metabolism of D/L‐, L‐ and D‐glufosinate in transgenic, glufosinate‐tolerant crops of maize (Zea mays L ssp mays) and oilseed rape (Brassica napus L var napus)

d‐glufosinate as a male sterility agent for hybrid seed production

Enantioselective hydrolyzation and photolyzation of dufulin in water

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