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PubMed1980

The Site of the Inhibition of the Shikimate Pathway by Glyphosate: II. INTERFERENCE OF GLYPHOSATE WITH CHORISMATE FORMATION IN VIVO AND IN VITRO.

In the presence of the nonselective herbicide glyphosate (N-[phosphonomethyl]glycine), buckwheat (Fagopyrum esculentum Moench) hypocotyls and cultured cells of Galium mollugo L. accumulate an organic acid, which was identified as shikimate by mass-spectroscopy of its methyl ester. After growth in 0.5 millimolar glyphosate for 10 days, G. mollugo cells contained shikimate in amounts of up to 10% of their dry weight. Synthesis of chorismate-derived anthraquinones in G. mollugo was blocked by glyphosate. Chorismate and o-succinylbenzoate (an anthraquinone precursor) alleviated the inhibition. The conclusion drawn from these experiments, that glyphosate inhibits a step in the biosynthetic sequence from shikimate to chorismate, was substantiated by the finding that glyphosate is a powerful inhibitor of the conversion of shikimate to chorismate in cell-free extracts from Aerobacter aerogenes 62-1.

Journal Article↗

PubMed2000

[Poisonings with the herbicides glyphosate and glyphosate-trimesium].

Generally the herbicide glyphosate is considered harmless to humans. Glyphosate-trimesium is labelled harmful (Xn), whereas glyphosate-isopropylamine carries no warning sign. As cases of serious poisoning have emerged contacts to the Poison Information Centre have been reviewed. The persons exposed were mainly smaller children and adults 20 to 59 years of age. Oral exposure was recorded in 47 persons, inhalation exposure in 24 and topical contact in 42. About one fourth of the exposed persons were asymptomatic. Most of the symptomatic poisonings demonstrated complaints from the mouth, the gastrointestinal tract and the airways. Eleven patients were admitted to hospital. Two died, one of them having ingested the isopropylamine salt, the other the trimesium salt. Death ensued quickly in the latter patient. A similar fate was observed in a child--not included in the present material--who had also ingested the trimesium compound.

Adult↗

PubMed2000

Glyphosate-tolerant corn: the composition and feeding value of grain from glyphosate-tolerant corn is equivalent to that of conventional corn (Zea mays L.).

Glyphosate-tolerant (Roundup Ready) corn line GA21 has been developed by genetic modification to tolerate glyphosate, the active ingredient in Roundup herbicide. The purpose of this study was to evaluate the compositional and nutritional safety of corn line GA21 compared to that of conventional corn. Compositional analyses were conducted to measure proximate, fiber, amino acid, fatty acid, and mineral contents of grain and proximate, fiber, and mineral contents of forage collected from 16 field sites over two growing seasons. The nutritional safety of corn line GA21 was evaluated in a poultry feeding study conducted with 2-day old, rapidly growing broiler chickens, at a dietary concentration of 50-60% w/w. Compositional analysis results showed that, except for a few minor differences that are unlikely to be of biological significance, the grain and forage of GA21 corn were comparable in their composition to that of the control corn line and to conventional corn. Results from the poultry feeding study showed that there were no differences in growth, feed efficiency, adjusted feed efficiency, and fat pad weights between chickens fed with GA21 grain or with parental control grain. These data taken together demonstrate that Roundup Ready corn is as safe and nutritious as conventional corn for food and feed use.

Amino Acids↗

PubMed2001

IR and EXAFS spectroscopic studies of glyphosate protonation and copper(II) complexes of glyphosate in aqueous solution.

The varying degrees of protonation of N-(phosphonomethyl)glycine (PMG, glyphosate) were investigated with infrared (IR) spectroscopy and ab initio frequency calculations. The zwitterionic nature of PMG in solution was confirmed, and intramolecular hydrogen bonding was identified. Successive protonation of the PMG molecule follows the order amine, phosphonate, carboxylate. Intramolecular hydrogen bonding is indicated to exist at all stages of protonation: between both RCO(2-) and RNH(2)(+) and RPO(3)(2-) and RNH(2+) in HL(2)(-) (where L represents the ligand PMG); between RCO(2)(-) and RNH(2)(+) in H(2)L(-); predominantly between RPO(3)(2-) and RNH(2)(+) in H(3)L. There are strong indications that the zwitterion is intact throughout the pH range investigated. Results from IR and extended X-ray absorption fine structure (EXAFS) spectroscopies provide new evidence for structures of N-(phosphonomethyl)glycinecopper(II) complexes. The structures of 1:1 complexes, CuL(-) and CuHL, are essentially the same, differing only in protonation of the phosphonate group. Copper(II) lies at the center of a Jahn-Teller distorted octahedron with all three donor groups (amine, carboxylate, phosphonate) of PMG chelating with copper(II) to form two five-membered chelate rings oriented in the equatorial plane. EXAFS indicates that oxygen (most likely a water molecule) is a fourth ligand, which would thus occupy the fourth corner in the equatorial plane of the elongated octahedron. CuL(2)(4-) most probably forms an isomeric mixture in solution, and there are indications that this mixture is dominated by complexes where two PMG ligands are bound to copper(II) via equatorial and axial positions, with both phosphonate and carboxylate donor groups responsible for chelation at axial positions.

Journal Article↗

PubMed2002

A mechanistic analysis of penetration of glyphosate salts across astomatous cuticular membranes.

Penetration of glyphosate salts across isolated poplar (Populus canescens (Aiton) Sm) cuticular membranes (CM) was studied using Na+, K+, NH4+, trimethylsulfonium+ (TMS) and isopropylamine+ (IPA) as cations. After droplet drying, humidity over the salt residues on the outer surfaces of the CM was kept constant, and cuticular penetration was monitored by sampling the receiver solution facing the inner surfaces of the CM. Glyphosate salts disappeared exponentially with time from the surfaces of the CM. This first-order process could be quantitatively described using rate constants (k) or half-times (time for 50% penetration; t1/2). Humidity strongly affected the velocity of penetration, as k increased by factors of 5.3 (K-glyphosate), 6.9 (TMS-glyphosate), 7.1 (NH4-glyphosate), 8.5 (Na-glyphosate) and 10.5 (IPA-glyphosate) when humidity was increased from 70 to 100%. Depending on the type of cation and humidity, t1/2 varied between 4 and 70h, but the humidity effect was statistically significant only at 100% humidity, when half-times were highest with IPA-glyphosate and lowest with TMS-glyphosate. Glyphosate acid penetration was measured only at 90% humidity and found to be extremely slow (t1/2 = 866 h). Adding 0.2 g litre-1 of a wetter (alkylpolyglucoside) to the donor increased IPA-glyphosate rate constants by about four times, but increasing concentration produced no further increase in k. When donors contained 0.2 g litre-1 wetter, further additions of 4 g litre-1 Ethomeen T25 did not change rate constants measured with IPA-glyphosate at 90% humidity, while Genapol C-100 and diethyl suberate increased k by only 35%. Concentration of IPA-glyphosate (1, 2 and 4 g litre-1) did not influence k at 90% humidity, and pH of donor solutions (4.0, 7.7, 9.5) had no effect on k of K-glyphosate at 90% humidity. Temperature (10 to 25 degrees C) had only a small influence on velocity of penetration of IPA-glyphosate and K-glyphosate, as energies of activation amounted to only 4.26 and 2.92 kJ mole-1, respectively. These results are interpreted as evidence for penetration of glyphosate salts in aqueous pores.

Cations↗

PubMed2006

Foliar-applied glyphosate substantially reduced uptake and transport of iron and manganese in sunflower (Helianthus annuus L.) plants.

Evidence clearly shows that cationic micronutrients in spray solutions reduce the herbicidal effectiveness of glyphosate for weed control due to the formation of metal-glyphosate complexes. The formation of these glyphosate-metal complexes in plant tissue may also impair micronutrient nutrition of nontarget plants when exposed to glyphosate drift or glyphosate residues in soil. In the present study, the effects of simulated glyphosate drift on plant growth and uptake, translocation, and accumulation (tissue concentration) of iron (Fe), manganese (Mn), zinc (Zn), and copper (Cu) were investigated in sunflower (Helianthus annuus L.) plants grown in nutrient solution under controlled environmental conditions. Glyphosate was sprayed on plant shoots at different rates between 1.25 and 6.0% of the recommended dosage (i.e., 0.39 and 1.89 mM glyphosate isopropylamine salt). Glyphosate applications significantly decreased root and shoot dry matter production and chlorophyll concentrations of young leaves and shoot tips. The basal parts of the youngest leaves and shoot tips were severely chlorotic. These effects became apparent within 48 h after the glyphosate spray. Glyphosate also caused substantial decreases in leaf concentration of Fe and Mn while the concentration of Zn and Cu was less affected. In short-term uptake experiments with radiolabeled Fe (59Fe), Mn (54Mn), and Zn (65Zn), root uptake of 59Fe and 54Mn was significantly reduced in 12 and 24 h after application of 6% of the recommended dosage of glyphosate, respectively. Glyphosate resulted in almost complete inhibition of root-to-shoot translocation of 59Fe within 12 h and 54Mn within 24 h after application. These results suggest that glyphosate residues or drift may result in severe impairments in Fe and Mn nutrition of nontarget plants, possibly due to the formation of poorly soluble glyphosate-metal complexes in plant tissues and/or rhizosphere interactions.

Biological Transport↗

PubMed2004

Glyphosate poisoning.

Glyphosate is used extensively as a non-selective herbicide by both professional applicators and consumers and its use is likely to increase further as it is one of the first herbicides against which crops have been genetically modified to increase their tolerance. Commercial glyphosate-based formulations most commonly range from concentrates containing 41% or more glyphosate to 1% glyphosate formulations marketed for domestic use. They generally consist of an aqueous mixture of the isopropylamine (IPA) salt of glyphosate, a surfactant, and various minor components including anti-foaming and colour agents, biocides and inorganic ions to produce pH adjustment. The mechanisms of toxicity of glyphosate formulations are complicated. Not only is glyphosate used as five different salts but commercial formulations of it contain surfactants, which vary in nature and concentration. As a result, human poisoning with this herbicide is not with the active ingredient alone but with complex and variable mixtures. Therefore, It is difficult to separate the toxicity of glyphosate from that of the formulation as a whole or to determine the contribution of surfactants to overall toxicity. Experimental studies suggest that the toxicity of the surfactant, polyoxyethyleneamine (POEA), is greater than the toxicity of glyphosate alone and commercial formulations alone. There is insufficient evidence to conclude that glyphosate preparations containing POEA are more toxic than those containing alternative surfactants. Although surfactants probably contribute to the acute toxicity of glyphosate formulations, the weight of evidence is against surfactants potentiating the toxicity of glyphosate. Accidental ingestion of glyphosate formulations is generally associated with only mild, transient, gastrointestinal features. Most reported cases have followed the deliberate ingestion of the concentrated formulation of Roundup (The use of trade names is for product identification purposes only and does not imply endorsement.) (41% glyphosate as the IPA salt and 15% POEA). There is a reasonable correlation between the amount ingested and the likelihood of serious systemic sequelae or death. Advancing age is also associated with a less favourable prognosis. Ingestion of >85 mL of the concentrated formulation is likely to cause significant toxicity in adults. Gastrointestinal corrosive effects, with mouth, throat and epigastric pain and dysphagia are common. Renal and hepatic impairment are also frequent and usually reflect reduced organ perfusion. Respiratory distress, impaired consciousness, pulmonary oedema, infiltration on chest x-ray, shock, arrythmias, renal failure requiring haemodialysis, metabolic acidosis and hyperkalaemia may supervene in severe cases. Bradycardia and ventricular arrhythmias are often present pre-terminally. Dermal exposure to ready-to-use glyphosate formulations can cause irritation and photo-contact dermatitis has been reported occasionally; these effects are probably due to the preservative Proxel (benzisothiazolin-3-one). Severe skin burns are very rare. Inhalation is a minor route of exposure but spray mist may cause oral or nasal discomfort, an unpleasant taste in the mouth, tingling and throat irritation. Eye exposure may lead to mild conjunctivitis, and superficial corneal injury is possible if irrigation is delayed or inadequate. Management is symptomatic and supportive, and skin decontamination with soap and water after removal of contaminated clothing should be undertaken in cases of dermal exposure.

Animals↗

PubMed2024

Revealing novel protein interaction partners of glyphosate in Escherichia coli.

Despite all debates about its safe use, glyphosate remains the most widely applied active ingredient in herbicide products, with renewed approval in the European Union until 2033. Non-target organisms are commonly exposed to glyphosate as a matter of its mode of application, with its broader environmental and biological impacts remaining under investigation. Glyphosate displays structural similarity to phosphoenolpyruvate (PEP), thereby competitively inhibiting the 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), crucial for the synthesis of aromatic amino acids in plants, fungi, bacteria, and archaea. Most microbes, including the gut bacterium Escherichia coli (E. coli), possess a glyphosate-sensitive class I EPSPS, making them vulnerable to glyphosate's effects. Yet, little is known about glyphosate's interactions with other bacterial proteins or its broader modes of action at the proteome level. Here, we employed a quantitative proteomics and thermal proteome profiling (TPP) approach to identify novel protein binding partners of glyphosate in the E. coli proteome. Glyphosate exposure significantly altered amino acid synthesizing pathways. The abundance of shikimate pathway proteins was increased, suggesting a compensatory mechanism. Extracellular riboflavin concentrations were elevated upon glyphosate exposure, while intracellular levels remained stable. Beyond the target enzyme EPSPS, thermal proteome profiling indicated an effect of glyphosate on the thermal stability of certain proteins, including AroH and ProA, indicating interactions. Similar to the competitive binding between PEP and glyphosate at EPSPS, one reason for the interaction of AroH and ProA with the herbicide could be a high structural similarity between their substrates and glyphosate. Overall, glyphosate induced metabolic disturbances in E. coli, extending beyond its primary target, thereby providing new insights into glyphosate's broader impact on microbial systems.

Glyphosate↗

PubMed2004

Interactions of calcium ions with weakly acidic active ingredients slow cuticular penetration: a case study with glyphosate.

Potassium and calcium salts of glyphosate were obtained by titrating glyphosate acid with the respective bases to pH 4.0, and rates of penetration of these salts across isolated astomatous cuticular membranes (CMs) were measured at 20 degrees C and 70, 80, 90, and 100% humidity. K-glyphosate exhibited first-order penetration kinetics, and rate constants (k) increased with increasing humidity. Ca-glyphosate penetrated only when the humidity above the salt residue was 100%. At 90% humidity and below, Ca-glyphosate formed a solid residue on the CMs and penetration was not measurable. With Ca-glyphosate, the k value at 100% humidity decreased with time and the initial rates were lower than for K-glyphosate by a factor of 3.68. After equimolar concentrations of ammonium oxalate were added to Ca-glyphosate, high penetration rates close to those measured with K-glyphosate were measured at all humidities. Adding ammonium sulfate or potassium carbonate also increased rates between 70 and 100% humidity, but they were not as high as with ammonium oxalate. The data indicate that at pH 4.0 one Ca2+ ion is bound to two glyphosate anions. This salt has its deliquescence point near 100% humidity. Therefore, it is a solid at lower humidity and does not penetrate. Its molecular weight is 1.82 times larger than that of K-glyphosate, and this greatly slows down rates of penetration, even at 100% humidity. The additives tested have low solubility products and form insoluble precipitates with Ca2+ ions, but only ammonium oxalate binds Ca2+ quantitatively. The resulting ammonium salt of glyphosate penetrates at 70-100% humidity and at rates comparable to K-glyphosate. The results contribute to a better understanding of the hard water antagonism observed with glyphosate. It is argued that other pesticides and hormones with carboxyl functions are likely to respond to Ca2+ ions in a similar fashion. In all of these cases, ammonium oxalate is expected to overcome hard water antagonism.

Ammonium Sulfate↗

PubMed2005

Differential response of Amaranthus tuberculatus (Moq ex DC) JD Sauer to glyphosate.

Midwest USA farmers have reported inconsistent control of Amaranthus tuberculatus (= rudis) (Moq ex DC) JD Sauer by glyphosate in glyphosate-resistant crops. The potential of selection for decreased A tuberculatus sensitivity to glyphosate was therefore investigated in a reportedly resistant Everly, IA population (P0-EV). Evaluation of six A tuberculatus populations from the Midwest USA estimated a seedling baseline sensitivity of 2.15 mM glyphosate. Based on these results, three generations of divergent recurrent selection were implemented on P0-EV to isolate resistant and susceptible populations. A seedling assay was developed to screen large amounts of seeds and thus expedite the selection process. Whole-plant and seedling rate responses of P0-EV and a known pristine A tuberculatus population from Paint Creek, OH (P0-WT) identified no significant difference in response to glyphosate; however, greater phenotypic variance was ostensibly evident in P0-EV. The first recurrent generation selected for resistance at 3.2 mM glyphosate (RS1-R) had a 5.9- and 1.7-fold resistance increase at the seedling and whole-plant levels, respectively, compared with the susceptible generation selected at 32 microM glyphosate. After three cycles of recurrent selection, 14.6-fold difference in resistance at the seedling level and 3.1-fold difference at the whole-plant level were observed when comparing the populations selected for resistance (RS3-R) and susceptibility (RS3-S). Overall, recurrent selection increased the frequency of resistant individuals and decreased the variability to glyphosate at the population level. Nevertheless, variability for glyphosate resistance was still evident in RS3-R. Results herein suggested that A tuberculatus is inherently variable to glyphosate and that selection decreased the sensitivity to glyphosate. We purport that evolved glyphosate resistance in A tuberculatus may require multiple cycles of selection under field conditions. Historic estimated use of glyphosate alludes to the evolution of tolerant weed populations.

Amaranthus↗

PubMed2005

Oxidative degradation of glyphosate and aminomethylphosphonate by manganese oxide.

Glyphosate (N-(phosphonomethyl)glycine), the most commonly used herbicide worldwide, degrades relatively rapidly in soils under most conditions, presumably by microbial processes. The most frequently detected degradation product in soil and water is AMPA (aminomethylphosphonic acid). We report the first evidence for an abiotic pathway of glyphosate and AMPA degradation under environmentally realistic conditions. Both glyphosate and AMPA degraded at 20 degrees C in dilute aqueous suspensions of birnessite, a manganese oxide common in soils, as evidenced by the accumulation of orthophosphate in solution over a period of several days. It is concluded that the abiotic degradation involved C-P bond cleavage at the Mn oxide surface, although evidence for C-N bond cleavage in the case of glyphosate and sarcosine, a likely degradation product of glyphosate, was found. The degradation of glyphosate was faster than that of AMPA, and higher temperature (50 degrees C) resulted in faster degradation of both glyphosate and AMPA. The addition of sulfate to the solution had no marked effect on the reaction rate, although Cu2+ addition inhibited degradation. As this metal ion complexes strongly with glyphosate, the inhibition can be attributed to the ability of Cu2+ to limit glyphosate coordination to reactive oxidation sites at the Mn oxide surface. Using a similar experimental design, we were unable to detect glyphosate degradation in an equimolar solution of MnCl2 (0.5 mM). However, we demonstrated that the oxidation of Mn2+ is enhanced both in solution and on an inert surface, in the presence of glyphosate (4:1 Mn-glyphosate molar ratio). This result suggests that the oxidative breakdown of glyphosate in the presence of Mn2+ may ultimately occur following the spontaneous oxygen-mediated oxidation of manganese.

Glycine↗

PubMed2005

[Cytotoxicity and genotoxicity of human cells exposed in vitro to glyphosate].

INTRODUCTION: Glyphosate is a broad-spectrum non-selective herbicide, used to eliminate unwanted weeds in agricultural and forest settings. Herbicide action is achieved through inhibition of aromatic amino acid biosynthesis in plant cells. Since this is not a conserved mechanism between human and plant cells, glyphosate is considered to be a low health risk substance for humans. However, the occurrence of possible harmful side effects of glyphosate use is not well documented and controversial. Toxicity and genotoxicity studies indicate that glyphosate is not harmful, although several investigations suggest that it can alter various cellular processes in animals. Therfore this has potential as a health and environmental risk factor in areas where glyphosate is widely used. OBJECTIVES: The present study evaluated glyphosate cytotoxic and genotoxic effects in normal human cells (GM38) and human fibrosarcoma (HT1080) cells. MATERIALS AND METHODS: Acute and chronic cytotoxicity were determined through the exposure of cultured cells to graded concentrations of glyphosate, and cell viability analysis was performed with crystal violet and Trypan blue staining. Genotoxicity was determined using the comet assay and data significance was evaluated with Dunnet's test. RESULTS: For chronic cytotoxicity a dose-dependent effect was observed in both GM38 and HT1080 cells after treatment with 5.2-8.5 mM and 0.9-3.0 mM glyphosate, respectively. In the acute cytotoxicity study, GM38 cells exposed to 4.0-7.0 mM glyphosate and HT1080 cells exposed to 4.5-5.8 mM glyphosate, had cell viability counts higher than 80%. Genotoxic effects were evidenced in GM38 cells at glyphosate concentrations of 4.0-6.5 mM and in HT1080 cells at glyphosate concentrations of 4.75 -5.75 mM. CONCLUSIONS: The levels of cytotoxicity and genotoxicity of glyphosate occurring in mammalian cells suggested that its mechanism of action is not limited to plant cells.

Cell Line↗

PubMed2004

Inheritance of evolved glyphosate resistance in Conyza canadensis (L.) Cronq.

N-(phosphonomethyl)glycine (glyphosate) resistance was previously reported in a horseweed [Conyza (=Erigeron) canadensis (L.) Cronq.] population from Houston, DE (P (0) (R) ). Recurrent selection was performed on P (0) (R) , since the population was composed of susceptible (5%) and resistant (95%) phenotypes. After two cycles of selection at 2.0 kg ae glyphosate ha(-1), similar glyphosate rates that reduced plant growth by 50%, glyphosate rates that inflicted 50% mortality in the population, and accumulations of half of the maximum detectable shikimic acid concentration were observed between the parental P (0) (R) and the first (RS(1)) and second (RS(2)) recurrent generations. In addition, RS(1) and RS(2) did not segregate for resistance to glyphosate. This suggested that the RS(2) population comprised a near-homozygous, glyphosate-resistant line. Whole-plant rate responses estimated a fourfold resistance increase to glyphosate between RS(2) and either a pristine Ames, IA (P (0) (P) ) or a susceptible C. canadensis population from Georgetown, DE (P (0) (S) ). The genetics of glyphosate resistance in C. canadensis was investigated by performing reciprocal crosses between RS(2) and either the P (0) (P) or P (0) (S) populations. Evaluations of the first (F(1)) and second (F(2)) filial generations suggested that glyphosate resistance was governed by an incompletely dominant, single-locus gene (R allele) located in the nuclear genome. The proposed genetic model was confirmed by back-crosses of the F(1) to plants that arose from achenes of the original RS(2), P (0) (P) , or P (0) (S) parents. The autogamous nature of C. canadensis, the simple inheritance model of glyphosate resistance, and the fact that heterozygous genotypes (F(1)) survived glyphosate rates well above those recommended by the manufacturer, predicted a rapid increase in frequency of the R allele under continuous glyphosate selection. The impact of genetics on C. canadensis resistance management is discussed.

Alleles↗

PubMed2005

Effects of phosphate on the adsorption of glyphosate on three different types of Chinese soils.

Glyphosate (GPS) is a non-selective, post-mergence herbicide that is widely used throughout the world. Due to the similar molecular structures of glyphosate and phosphate, adsorption of glyphosate on soil is easily affected by coexisting phosphate, especially when phosphate is applied at a significant rate in farmland. This paper studied the effects of phosphate on the adsorption of glyphosate on three different types of Chinese soils including two variable charge soils and one permanent charge soil. The results indicated that Freundlich equations used to simulate glyphosate adsorption isotherms gave high correlation coefficients (0.990-0.998) with K values of 2751, 2451 and 166 for the zhuanhong soil(ZH soil, Laterite), red soil(RS, Udic Ferrisol) and Wushan paddy soil (WS soil, Anthrosol), respectively. The more the soil iron and aluminum oxides and clay contained, the more glyphosate adsorbed. The presence of phosphate significantly decreased the adsorption of glyphosate to the soils by competing with glyphosate for adsorption sites of soils. Meanwhile, the effects of phosphate on adsorption of glyphosate on the two variable charge soils were more significant than that on the permanent charge soil. When phosphate and glyphosate were added in the soils in different orders, the adsorption quantities of glyphosate on the soils were different, which followed GPS-soil > GPS-P-soil = GPS-soil-P > P-soil-GPS, meaning a complex interaction occurred among glyphosate, phosphate and the soils.

Adsorption↗

PubMed2000

Safety evaluation and risk assessment of the herbicide Roundup and its active ingredient, glyphosate, for humans.

Reviews on the safety of glyphosate and Roundup herbicide that have been conducted by several regulatory agencies and scientific institutions worldwide have concluded that there is no indication of any human health concern. Nevertheless, questions regarding their safety are periodically raised. This review was undertaken to produce a current and comprehensive safety evaluation and risk assessment for humans. It includes assessments of glyphosate, its major breakdown product [aminomethylphosphonic acid (AMPA)], its Roundup formulations, and the predominant surfactant [polyethoxylated tallow amine (POEA)] used in Roundup formulations worldwide. The studies evaluated in this review included those performed for regulatory purposes as well as published research reports. The oral absorption of glyphosate and AMPA is low, and both materials are eliminated essentially unmetabolized. Dermal penetration studies with Roundup showed very low absorption. Experimental evidence has shown that neither glyphosate nor AMPA bioaccumulates in any animal tissue. No significant toxicity occurred in acute, subchronic, and chronic studies. Direct ocular exposure to the concentrated Roundup formulation can result in transient irritation, while normal spray dilutions cause, at most, only minimal effects. The genotoxicity data for glyphosate and Roundup were assessed using a weight-of-evidence approach and standard evaluation criteria. There was no convincing evidence for direct DNA damage in vitro or in vivo, and it was concluded that Roundup and its components do not pose a risk for the production of heritable/somatic mutations in humans. Multiple lifetime feeding studies have failed to demonstrate any tumorigenic potential for glyphosate. Accordingly, it was concluded that glyphosate is noncarcinogenic. Glyphosate, AMPA, and POEA were not teratogenic or developmentally toxic. There were no effects on fertility or reproductive parameters in two multigeneration reproduction studies with glyphosate. Likewise there were no adverse effects in reproductive tissues from animals treated with glyphosate, AMPA, or POEA in chronic and/or subchronic studies. Results from standard studies with these materials also failed to show any effects indicative of endocrine modulation. Therefore, it is concluded that the use of Roundup herbicide does not result in adverse effects on development, reproduction, or endocrine systems in humans and other mammals. For purposes of risk assessment, no-observed-adverse-effect levels (NOAELs) were identified for all subchronic, chronic, developmental, and reproduction studies with glyphosate, AMPA, and POEA. Margins-of-exposure for chronic risk were calculated for each compound by dividing the lowest applicable NOAEL by worst-case estimates of chronic exposure. Acute risks were assessed by comparison of oral LD50 values to estimated maximum acute human exposure. It was concluded that, under present and expected conditions of use, Roundup herbicide does not pose a health risk to humans.

Abnormalities, Drug-Induced↗

PubMed2006

Glyphosate, paraquat and ACCase multiple herbicide resistance evolved in a Lolium rigidum biotype.

Glyphosate is the world's most widely used herbicide. A potential substitute for glyphosate in some use patterns is the herbicide paraquat. Following many years of successful use, neither glyphosate nor paraquat could control a biotype of the widespread annual ryegrass (Lolium rigidum), and here the world's first case of multiple resistance to glyphosate and paraquat is confirmed. Dose-response experiments established that the glyphosate rate causing 50% mortality (LD(50)) for the resistant (R) biotype is 14 times greater than for the susceptible (S) biotype. Similarly, the paraquat LD(50 )for the R biotype is 32 times greater than for the S biotype. Thus, based on the LD(50 )R/S ratio, this R biotype of L. rigidum is 14-fold resistant to glyphosate and 32-fold resistant to paraquat. This R biotype also has evolved resistance to the acetyl-coenzyme A carboxylase (ACCase) inhibiting herbicides. The mechanism of paraquat resistance in this biotype was determined as restricted paraquat translocation. Resistance to ACCase-inhibiting herbicides was determined as due to an insensitive ACCase. Two mechanisms endowing glyphosate resistance were established: firstly, a point mutation in the 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) gene, resulting in an amino acid substitution of proline to alanine at position 106; secondly, reduced glyphosate translocation was found in this R biotype, indicating a co-occurrence of two distinct glyphosate resistance mechanisms within the R population. In total, this R biotype displays at least four co-existing resistance mechanisms, endowing multiple resistance to glyphosate, paraquat and ACCase herbicides. This alarming case in the history of herbicide resistance evolution represents a serious challenge for the sustainable use of the precious agrochemical resources such as glyphosate and paraquat.

3-Phosphoshikimate 1-Carboxyvinyltransferase↗

PubMed2004

Adsorption and cosorption of cadmium and glyphosate on two soils with different characteristics.

Glyphosate [N-(phosphonomethyl)glycine] (GPS; H3G) is a widely used pesticide throughout the world. It affects metal behaviors in soil-plant system due to its functional groups, which react with metal ions to form metal complexes. Adsorption and cosorption of cadmium and glyphosate on a Wushan soil (WS soil, Anthrosol) and a Zhuanhong soil (ZH soil, Udic Ferrisol) as affect by solution pH were studied by means of batch adsorption experiments. It indicated that the adsorption quantity of Cd or glyphosate was highly relevant to soil characteristics. The WS soil had higher adsorption capacity of Cd than the ZH soil, due to its high organic matter content and cation exchange capacity (CEC). In contrast, the adsorption quantity of glyphosate on the WS soil was less than that on the ZH soil, because the WS soil has lower iron and aluminum oxides content but higher pH than the ZH soil. The herbicide glyphosate affected Cd adsorption on the two soils when they coexisted in a same soil solution, which was attributed to a glyphosate-induced pH-decrease and the corresponding decline in negative surface charges of the soil. Beside that, glyphosate reacted with solution Cd to form the water-soluble complexes that had lower affinity to soil surface in comparison with Cd itself. On the other hand, the presence of Cd in the soil solution also affected the adsorption of glyphosate on the soils. The presence of Cd increased adsorption quantity of glyphosate on the WS and ZH soils, which was resulted from the decrease of equilibrium solution pH caused by Cd2+ exchange with H+ ions of soil surface. In addition to that, glyphosate adsorption possibly takes place on sites where Cd was previously adsorbed and acted as a bridge between the soil and glyphosate.

Adsorption↗

PubMed2006

Identification of Arabidopsis thaliana variants with differential glyphosate responses.

To facilitate future investigations of glyphosate-resistance mechanisms, three approaches were taken to obtain Arabidopsis thaliana variants that differed in glyphosate response. Recurrent selection by spraying with sub-lethal glyphosate concentrations was performed with Columbia-0 seedlings. After seven cycles of treatment, no resistance was found. A population of 800,000 ethylmethanesulfonate-mutagenized M(2) seedlings was screened on agar containing 0.2mM glyphosate, a lower concentration than that previously used in other studies, and no resistant mutants were recovered. Seventy-two Arabidopsis ecotypes were screened with glyphosate and a range of responses was observed. In a follow-up experiment on a subset of these ecotypes, reduction of seed yield by 11.5 g/ha glyphosate (about 1% the typical field use rate) ranged among ecotypes from 0% to >90%, relative to untreated controls. However, even the least sensitive ecotypes were severely injured by relatively low glyphosate rates. Overall, attempts to select Arabidopsis seedlings that were significantly glyphosate-resistant were unsuccessful and consistent with previous reports. Arabidopsis ecotypes identified with differential glyphosate responses could be used for further studies though the inherently high sensitivity of Arabidopsis to glyphosate could limit their utility in studying glyphosate-resistance mechanisms.

Arabidopsis↗