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PubMed2001

Dynamics of glyphosate and aminomethylphosphonic acid in a forest soil in Galicia, north-west Spain.

Residues of the herbicide glyphosate (N-phosphonomethylglicine) and its main metabolite, aminomethylphosphonic acid (AMPA), were determined in a forest soil in north-west Spain, previously treated with 5 and 8 l ha(-1) of glyphosate. Both products were monitored in the solid and liquid soil phases for an 8-week period after the treatment. Soil samples were extracted by KH2PO4. Concentrated extracts and liquid phase samples were derivatized with 9-fluorenylmethyl chloroformate (FMOC) before determination by HPLC using an anion exchange column and spectrofluorometric detection. The treated soil peaked at 6.9 microg g(-1) of glyphosate, whereas soil water samples peaked at 0.74 microg ml(-1) of glyphosate. One month after the treatment, both glyphosate and AMPA concentrations in soil and water samples were almost negligible. AMPA peaked at 0.77 microg ml(-1) in soil water samples. Glyphosate and AMPA exhibited high vertical mobility in the treated soil, quickly reaching high concentrations in subsurface horizons where the degradation is slower.

Environmental Monitoring↗

PubMed2006

Molecular orbital theory study on surface complex structures of glyphosate on goethite: calculation of vibrational frequencies.

Six possible complexes of glyphosate (O-PO(OH)-CH2NH2+CH2CO2H) with an Fe-hydroxide dimer were modeled with hybrid molecular orbital/density functional theory calculations to establish the nature of the bonds of glyphosate on goethite (alpha-FeOOH). Monodentate and bidentate coordination of the phosphonate moiety were considered, using three forms of the glyphosate molecule appropriate for different pH ranges: glyphosate with both phosphonate and amino moieties protonated, glyphosate with unprotonated phosphonates, and glyphosate with both unprotonated phosphonates and no hydrogen ion on the amino group. The calculated infrared vibrational modes were compared to experimental values, finding particularly good agreements with the monodentate complexes in all the pH ranges.

Adsorption↗

PubMed2004

A novel approach to determine the glyphosate tolerant trait in soybeans.

The ability of soybean breeders to accurately, economically, and rapidly determine the transfer of the CP4 gene, the gene which confers soybean tolerance to the herbicide glyphosate, to elite soybean lines is essential to development of new glyphosate tolerant soybean (GTS) cultivars. This research focused on a simple greenhouse screening procedure to replace large, costly, and laborious field screening. Non-GTS seed was determined to be susceptible to soaking in a 1% glyphosate solution for 4 h. This process is quicker, more efficient, and as reliable as field screening for determination of glyphosate susceptibility in soybean seed. Furthermore, this research clearly demonstrates that the metabolic pathway of glyphosate activity, the shikimate acid pathway, is active, and the target enzyme of glyphosate, 5-enol-pyruvyl-shikimate-3-phosphate synthase, is present during seed germination.

Absorption↗

PubMed2004

Simultaneous quantification of glyphosate, glufosinate, and their major metabolites in rice and soybean sprouts by gas chromatography with pulsed flame photometric detector.

Procedures were developed for the simultaneous determination of glyphosate [N-(phosphonomethyl)glycine] and glufosinate [dl-homoalanin-4-yl-(methyl)phosphinic acid] and their major metabolites, aminomethylphosphonic acid (AMPA) and 3-(methylphosphinico)propionic acid (3-MPPA), in rice and soybean sprouts by gas chromatography (GC) equipped with a pulsed flame photometric detector (PFPD). Herbicides and their major metabolites were previously derivatized with TMOA (trimethyl orthoacetate (TMOA) in the presence of acetic acid, and their GC responses versus heating temperature (70-90 degrees C) and heating time (30-120 min) were optimized. It was found that increases in heating temperature and heating time were unfavorable for the derivatization of glyphosate or glufosinate, whereas high temperature and extended reaction time remarkably facilitated that of AMPA and 3-MPPA except at 90 degrees C for an extended reaction time (120 min). Combination of AG1-X8 anion-exchange chromatography with a Florisil cartridge cleanup process was favorable for the GC-PFPD analysis. Four types of derivatives spiked in rice and soybean sprout matrices were eluted, reaching a baseline separation, in a sequence of 3-MPPA, AMPA, glyphosate, and glufosinate within 14 min using a DB-608 capillary column. Recoveries of glyphosate, AMPA, glufosinate, and 3-MPPA (0.5 ppm) spiked in both sample matrices were determined to be 72-81, 71-86, 101-119, and 83-90%, respectively, whereas the coefficient of variation was determined to be <10% in three repeated determinations. The instrumental limits of detection for glyphosate, AMPA, glufosinate, and 3-MPPA in sample matrices were 0.02, 0.03, 0.02, and 0.01 ppm, respectively. The limits of quantification for glyphosate, AMPA, glufosinate, and 3-MPPA in sample matrices were 0.06, 0.10, 0.06, and 0.04 ppm, respectively.

Aminobutyrates↗

PubMed2006

New insights on glyphosate mode of action in nodular metabolism: Role of shikimate accumulation.

The short-term effects of the herbicide glyphosate (1.25-10 mM) on the growth, nitrogen fixation, carbohydrate metabolism, and shikimate pathway were investigated in leaves and nodules of nodulated lupine plants. All glyphosate treatments decreased nitrogenase activity rapidly (24 h) after application, even at the lowest and sublethal dose used (1.25 mM). This early effect on nitrogenase could not be related to either damage to nitrogenase components (I and II) or limitation of carbohydrates supplied by the host plant. In fact, further exposure to increasing glyphosate concentrations (5 mM) and greater time after exposure (5 days) decreased nodule starch content and sucrose synthase (SS; EC 2.4.1.13) activity but increased sucrose content within the nodule. These effects were accompanied by a great inhibition of the activity of phosphoenolpyruvate carboxylase (PEPC; EC 4.1.1.31). There were remarkable and rapid effects on the increase of shikimic and protocatechuic (PCA) acids in nodules and leaves after herbicide application. On the basis of the role of shikimic acid and PCA in the regulation of PEPC, as potent competitive inhibitors, this additional effect provoked by glyphosate on 5-enolpyruvylshikimic-3-phosphate synthase enzyme (EPSPS; EC 2.5.1.19) inhibition would divert most PEP into the shikimate pathway, depriving energy substrates to bacteroids to maintain nitrogen fixation. These findings provide a new explanation for the effectiveness of glyphosate as a herbicide in other plant tissues, for the observed differences in tolerance among species or cultivars, and for the transitory effects on glyphosate-resistant transgenic crops under several environmental conditions.

Carbohydrate Metabolism↗

PubMed1999

Development of an enzyme-linked immunosorbent assay for the detection of glyphosate.

A competitive indirect enzyme-linked immunosorbent assay (CI-ELISA) was developed to quantitate the herbicide glyphosate [N-(phosphonomethyl)glycine] in water. The ELISA has a detection limit of 7.6 microg mL(-1) and a linear working range of 10-1000 microg mL(-1) with an IC(50) value of 154 microg mL(-1). The glyphosate polyclonal antisera did not cross-react with a number of other herbicides tested but did cross-react with the glyphosate metabolite aminomethylphosphonic acid and a structurally related herbicide, glyphosine [(N,N-bis(phosphonomethyl)glycine]. The assay was used to estimate, quantitatively with accuracy and precision, glyphosate concentrations in water samples. Water samples were analyzed directly, and no sample preparation was required. To improve detection limits, water samples were concentrated prior to analysis, resulting in the increase of the detection limits by 100-fold. After the sample preconcentration step, the detection limit improved to 0.076 microg mL(-1) with an IC(50) value of 1.54 microg mL(-1), and a linear working range was 0.1-10 microg mL(-1). Glyphosate concentrations determined by ELISA correlated well with those determined by high-pressure liquid chromatography (r(2) = 0.99). This assay contributes to reducing the costs associated with conventional residue analysis techniques for the quantitation of glyphosate in water.

Chromatography, High Pressure Liquid↗

PubMed2005

Alternative herbicides to manage Italian ryegrass (Lolium multiflorum lam) resistant to glyphosate at different phenological stages.

During the growing season of 2002--2003, field and greenhouse experiments were conducted with the objective of evaluating the influence of Italian ryegrass phenological stages and management alternatives on the control of resistant biotypes to glyphosate. Three field experiments were conducted in Lagoa Vermelha, RS, Brazil and glyphosate was applied alone and in combinations with alternative herbicides. Two greenhouse experiments were also conducted at the Department of Crop Science, ESALQ/USP, Piracicaba, SP, Brazil. The Italian ryegrass resistant population was collected from Lagoa Vermelha, RS, Brazil. From the results it was possible to conclude that: (i) the more advanced the phenological stage of application, the more difficult the control of resistant Italian ryegrass by glyphosate, mainly by the rate of 960 g a.i. ha(-1); however, this rate applied at earlier phenological stage (five tillers), the control was higher than 90%; (ii) with the increment of glyphosate rate, it significant response was observed on the control at all stages of application; (iii) the mixture of glyphosate + clethodim (1440 + 72 g a.i. ha(-1)), paraquat + diuron (500 + 250 g a.i. ha(-1)), at all stages of application and clethodim (96 g a.i. ha(-1)) and paraquat + diuron (300 + 150 g a.i. ha(-1)) at the initial stages until pre-flowering were excellent alternatives for management of these populations; and (iv) the response of control was much faster for the mixture of glyphosate + clethodim, independently of growth stage.

Adaptation, Physiological↗

PubMed2001

Glyphosate inhibits melanization of Cryptococcus neoformans and prolongs survival of mice after systemic infection.

Cryptococcus neoformans is a major fungal pathogen and is a relatively common cause of life-threatening meningoencephalitis. Glyphosate is a widely used herbicide that inhibits the synthesis of aromatic amino acids via the shikimate acid pathway. This study investigated the effects of glyphosate on C. neoformans growth, melanization, and murine infection. C. neoformans was relatively resistant to glyphosate, requiring concentrations >250 microg/mL for inhibition. Melanization of C. neoformans in the presence of L-dopa was inhibited by subinhibitory concentrations of glyphosate. Glyphosate inhibited autopolymerization of L-dopa and oxidation of L-epinephrine by cryptococcal cells, which is mediated by a laccase. Administration of glyphosate to mice infected with C. neoformans delayed melanization of yeast cells in vivo and prolonged average mouse survival. The results suggest that inhibition of melanization in vivo may facilitate control of C. neoformans infection.

Animals↗

PubMed1984

5-Enolpyruvylshikimate-3-phosphate synthase of Klebsiella pneumoniae 2. Inhibition by glyphosate [N-(phosphonomethyl)glycine].

The broad-spectrum, non-selective herbicide glyphosate [N-(phosphonomethyl)glycine] is a potent inhibitor of highly purified 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase (3-phosphoshikimate 1-carboxyvinyltransferase, EC 2.5.1.19) of Klebsiella pneumoniae. The inhibition is competitive with phosphoenolpyruvate (PEP) with Ki = 1 microM at pH 6.8 and non-competitive with shikimate 3-phosphate, EPSP, and inorganic phosphate. Non-herbicidal analogues of glyphosate, such as aminomethylphosphonic acid, bis-N-(phosphonomethyl)glycine and iminodiacetic acid, do not inhibit the enzyme. Inhibition of EPSP synthase by glyphosate strongly increases with increasing pH. Glyphosate protects the enzyme against inactivation by phenylglyoxal, 3-bromopyruvate, and N-ethylmaleimide. It is proposed that glyphosate binds to the PEP-binding site of EPSP synthase as a transition-state analogue of PEP. Other PEP-utilizing enzymes were not found to be subject to inhibition by glyphosate.

3-Phosphoshikimate 1-Carboxyvinyltransferase↗

PubMed2004

Discovery and directed evolution of a glyphosate tolerance gene.

The herbicide glyphosate is effectively detoxified by N-acetylation. We screened a collection of microbial isolates and discovered enzymes exhibiting glyphosate N-acetyltransferase (GAT) activity. Kinetic properties of the discovered enzymes were insufficient to confer glyphosate tolerance to transgenic organisms. Eleven iterations of DNA shuffling improved enzyme efficiency by nearly four orders of magnitude from 0.87 mM-1 min-1 to 8320 mM-1 min-1. From the fifth iteration and beyond, GAT enzymes conferred increasing glyphosate tolerance to Escherichia coli, Arabidopsis, tobacco, and maize. Glyphosate acetylation provides an alternative strategy for supporting glyphosate use on crops.

Acetylation↗

PubMed1999

Rapid lethal intoxication caused by the herbicide glyphosate-trimesium (Touchdown).

Two cases of rapid lethal intoxication with the herbicide glyphosate-trimesium (Touchdown) are presented. A 6-year-old boy who accidentally ingested a mouthful of glyphosate-trimesium died within minutes. The same happened to a 34-year-old woman who intentionally ingested approximately 150 ml of glyphosate-trimesium. The post-mortem examination revealed gastric content and oedema of the mucus membranes of the airways, erosion of the mucus membranes of the gastrointestinal tract, pulmonary oedema, cerebral oedema, and dilated right atrium and ventricle of the heart. The speed of which death occurs is much more rapid than lethal intoxications with the herbicide glyphosate (isoprophylamine), also known as 'Roundup'. It is suggested that the lethal mechanism between the two herbicides may be different. The component, trimethylsulfonium, of the glyphosate-trimesium may facilitate the absorption after oral ingestion. This difference can be crucial in the treatment of human intoxication. We propose that containers with glyphosate-trimesium must be labelled because of the apparent effect of lethal intoxication.

Adult↗

PubMed1998

Safety assessment of genetically engineered food: detection and monitoring of glyphosate-tolerant soybeans.

A detection technique for the genetically engineered food, glyphosate-tolerant soybean (GTS), was designed. Commercial soybeans imported from North America were cultured in pots and genomic DNA was isolated from their leaves. To detect the genes, promoter and terminator, involved in the expression of glyphosate tolerance, PCR was done using the genomic DNA and chemically synthesized primers specific to the genes. DNAs with predicted sizes were amplified and confirmed by DNA sequencing to be the genes responsible for the expression of glyphosate tolerance. Glyphosate-tolerant soybeans were found to form approximately 1.1% of the commercial soybeans, when commercially available soybeans were cultivated and number of soybeans resistant to glyphosate was found. This level is somewhat lower than an estimated value announced officially on the basis of the cultivation area of the glyphosate-tolerant soybeans.

Base Sequence↗

PubMed2004

Glyphosate biomonitoring for farmers and their families: results from the Farm Family Exposure Study.

Glyphosate is the active ingredient in Roundup agricultural herbicides and other herbicide formulations that are widely used for agricultural, forestry, and residential weed control. As part of the Farm Family Exposure Study, we evaluated urinary glyphosate concentrations for 48 farmers, their spouses, and their 79 children (4-18 years of age). We evaluated 24-hr composite urine samples for each family member the day before, the day of, and for 3 days after a glyphosate application. Sixty percent of farmers had detectable levels of glyphosate in their urine on the day of application. The geometric mean (GM) concentration was 3 ppb, the maximum value was 233 ppb, and the highest estimated systemic dose was 0.004 mg/kg. Farmers who did not use rubber gloves had higher GM urinary concentrations than did other farmers (10 ppb vs. 2.0 ppb). For spouses, 4% had detectable levels in their urine on the day of application. Their maximum value was 3 ppb. For children, 12% had detectable glyphosate in their urine on the day of application, with a maximum concentration of 29 ppb. All but one of the children with detectable concentrations had helped with the application or were present during herbicide mixing, loading, or application. None of the systemic doses estimated in this study approached the U.S. Environmental Protection Agency reference dose for glyphosate of 2 mg/kg/day. Nonetheless, it is advisable to minimize exposure to pesticides, and this study did identify specific practices that could be modified to reduce the potential for exposure.

Adolescent↗

PubMedDate not supplied

Leaching of glyphosate and amino-methylphosphonic acid from Danish agricultural field sites.

Pesticide leaching is an important process with respect to contamination risk to the aquatic environment. The risk of leaching was thus evaluated for glyphosate (N-phosphonomethyl-glycine) and its degradation product AMPA (amino-methylphosphonic acid) under field conditions at one sandy and two loamy sites. Over a 2-yr period, tile-drainage water, ground water, and soil water were sampled and analyzed for pesticides. At a sandy site, the strong soil sorption capacity and lack of macropores seemed to prevent leaching of both glyphosate and AMPA. At one loamy site, which received low precipitation with little intensity, the residence time within the root zone seemed sufficient to prevent leaching of glyphosate, probably due to degradation and sorption. Minor leaching of AMPA was observed at this site, although the concentration was generally low, being on the order of 0.05 microg L(-1) or less. At another loamy site, however, glyphosate and AMPA leached from the root zone into the tile drains (1 m below ground surface [BGS]) in average concentrations exceeding 0.1 microg L(-1), which is the EU threshold value for drinking water. The leaching of glyphosate was mainly governed by pronounced macropore flow occurring within the first months after application. AMPA was frequently detected more than 1.5 yr after application, thus indicating a minor release and limited degradation capacity within the soil. Leaching has so far been confined to the depth of the tile drains, and the pesticides have rarely been detected in monitoring screens located at lower depths. This study suggests that as both glyphosate and AMPA can leach through structured soils, they thereby pose a potential risk to the aquatic environment.

Agriculture↗

PubMed2001

Adjuvant influence on glyphosate efficacy in the presence of CA2+.

Calcium ion in the spray water diminishes the efficacy of glyphosate. Ammonium sulphate (AS) is long shown to be the most efficacious remedy to this antagonism. However, it is sometimes claimed that acidified lecithins or terpenic alcohols can also be used to this aim, and even ethoxylated amines (EA) provided that calcium concentrations are not higher than 5 mM. We investigated these claims by examining dose-response curves of barley plants treated with glyphosate at various calcium concentrations in the presence of these adjuvants. Calcium ion increased the slope of the curves and ED50 values, indicating a decrease in efficacy. Acidified lecithins and terpenic alcohols did not modify the response of barley to glyphosate observed in the presence of calcium ion. AS restored the ED50 and slope values observed in the absence of calcium ion. It was concluded that the inhibition of glyphosate efficacy by calcium ion was not relieved by terpenic alcohols and acidified lecithins but was completely reverted by AS. EA decreased ED50 and ED90 values of the response curves established in the presence of calcium ion without influencing the slopes (which remained high). As a consequence, at calcium concentrations up to 5 mM the response curves obtained with AS and EA intersected. It followed that in the presence of EA, ED50 values were higher than AS, whereas ED90 values were lower. By contrast, at 10 mM calcium the response curves did not intersect and consequently, in the presence of EA, ED50 and ED90 values were both higher than AS. Since ED90 relates to efficacies sought in the field, our experiments explain why at low calcium concentrations EA may appear as a better remedy than AS. Glyphosate formulations containing ammonium sulphate or a higher concentration in surfactants than usual glyphosate formulations were also studied. In the presence of calcium ion they behaved in a way which was in agreement with the above observations.

Alcohols↗

PubMed2005

[Effects of glyphosate on life histroy characteristics of freshwater rotifer Brachionus calyciflorus].

The life table study on the life history characteristics of freshwater rotifer Brachionus calyciflorus under effects of different concentrations glyphosate showed that glyphosate had significant effects on the embryonic developmental time, duration of juvenile and reproductive periods, average lifespan, net reproductive rate, and intrinsic population increasing rate of the rotifer. The embryonic developmental time was significantly lengthened when exposed to 3 and 8 mg x L(-1) glyphosate, the juvenile period began to be lengthened significantly when exposed to 3 mg x L(-1) glyphosate, while the net reproductive rate and intrinsic population increasing rate decreased significantly when the rotifer was exposed to 8.00 and 10.50 mg x L(-1) glyphosate, respectively. Among all the parameters, intrinsic population increasing rate was the most sensitive parameter which could be used in monitoring the effects of glyphosate on the life history characteristics of B. calyciflorus.

Animals↗

PubMed2005

Glyphosate resistance in a Chilean Lolium multiflorum.

Lolium multiflorum (Italian ryegrass) has recently demonstrated itself to be poorly controlled with glyphosate in cereal crops of South Chile. The concentration of glyphosate necessary to reduce shoot length by 50% (ED50) in seedlings, after eight days of root contact was 7.3-fold in the resistant Vil-1 than in the susceptible (S) biotype. The obtained spray retention values were higher on S than the resistant (Vil-1) biotype. Contact angles measured on the adaxial surface of S and Vil-1 were similar. However, on the abaxial surface contact angles were of 63 degrees on Vil-1 as compared to 42 degrees on S. A greater glyphosate uptake was observed through the abaxial surface of S. Regarding translocation, glyphosate accumulated mainly in the tip of the treated leaf of Vil-1, 24 h after treatment. It was afterwards also well distributed to the rest of the leaves and roots, as in the susceptible biotype. Nevertheless, 14C-glyphosate remained higher in the foliar apex of Vil-1. Hence, resistance to glyphosate by the Vil-1 Lolium multflorum biotype seems to involve a lower uptake through the abaxial leaf surface and a different migration pattern.

Adaptation, Physiological↗

PubMed1985

Solid-state NMR determination of glyphosate metabolism in a Pseudomonas sp.

The metabolism of the broad-spectrum herbicide, glyphosate (N-phosphonomethylglycine) in a soil Pseudomonas sp. PG2982 has been determined by cross-polarization magic-angle spinning 15N and 13C NMR of intact lyophilized cells. Using samples grown on 13C- and 15N-labeled glyphosate, we find that PG2982 does not metabolize glyphosate to aminomethylphosphonate as has been reported for mixed cultures of soil microbes. Rather, the phosphonomethyl carbon-nitrogen bond in glyphosate is cleaved, releasing glycine. Solid-state NMR analysis reveals that 20% of this glycine is used in the synthesis of purines, 35% is incorporated into protein as glycyl residues, with an additional 35% incorporated as seryl residues. The phosphonomethyl carbon of glyphosate is ultimately incorporated into a number of sites, including the C-2 and C-8 positions of the purine rings of nucleic acids, methyl groups of methionine and thymidine, and the methylene group of serine. The pattern of phosphonomethyl carbon incorporation indicates the involvement of tetrahydrofolate, a coenzyme which facilitates single-carbon transfers. This is the first complete determination of the metabolism of glyphosate in a pure culture, and the first bacterial metabolic study using both single and double cross-polarization solid-state NMR.

Biodegradation, Environmental↗