Misplaced Pages

This is an old revision of this page, as edited by Bcebul (talk | contribs) at 20:34, 22 June 2013 (→Human: add reference to human toxicity review). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Glyphosate

Names
IUPAC name N-(phosphonomethyl)glycine
Other names 2-acetic acid
Identifiers
CAS Number	1071-83-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27744
ChEMBL	ChEMBL95764
ChemSpider	3376
ECHA InfoCard	100.012.726
KEGG	C01705
PubChem CID	3496
RTECS number	MC1075000
UNII	4632WW1X5A
CompTox Dashboard (EPA)	DTXSID1024122
InChI InChI=1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)Key: XDDAORKBJWWYJS-UHFFFAOYSA-N InChI=1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)Key: XDDAORKBJWWYJS-UHFFFAOYAE
SMILES O=C(O)CNCP(=O)(O)O
Properties
Chemical formula	C3H8NO5P
Molar mass	169.073 g·mol
Appearance	white crystalline powder
Density	1.704 (20 °C)
Melting point	184.5 °C
Boiling point	decomposes at 187 °C
Solubility in water	1.01 g/100 mL (20 °C)
log P	−2.8
Acidity (pKa)	<2, 2.6, 5.6, 10.6
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H411
Precautionary statements	P273, P280, P305+P351+P338, P310, P501
Flash point	non-flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Glyphosate (N-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide used to kill weeds, especially annual broadleaf weeds and grasses known to compete with commercial crops grown around the globe. It was discovered to be a herbicide by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market in the 1970s under the trade name Roundup, and Monsanto's last commercially relevant United States patent expired in 2000.

Glyphosate "more closely approximates to a perfect herbicide than any other." Glyphosate was quickly adopted by farmers, even more so when Monsanto introduced glyphosate-resistant crops, enabling farmers to kill weeds without killing their crops. In 2007 glyphosate was the most used herbicide in the United States agricultural sector, with 180 to 185 million pounds (82,000 to 84,000 tonnes) applied, and the second most used in home and garden market where users applied 5 to 8 million pounds (2,300 to 3,600 tonnes); additionally industry, commerce and government applied 13 to 15 million pounds (5,900 to 6,800 tonnes). With its heavy use in agriculture, weed resistance to glyphosate is a growing problem. While glyphosate has been approved by regulatory bodies worldwide and is widely used, concerns about its effects on humans and the environment persist.

Glyphosate's mode of action is to inhibit an enzyme involved in the synthesis of the aromatic amino acids tyrosine, tryptophan and phenylalanine. It is absorbed through foliage and translocated to growing points. Because of this mode of action, it is only effective on actively growing plants; it is not effective as a pre-emergence herbicide.

Some crops have been genetically engineered to be resistant to it (i.e. Roundup Ready, also created by Monsanto Company). Such crops allow farmers to use glyphosate as a post-emergence herbicide against both broadleaf and cereal weeds, but the development of similar resistance in some weed species is emerging as a costly problem. Soy was the first Roundup Ready crop.

Chemistry

Glyphosate is an aminophosphonic analogue of the natural amino acid glycine, and the name is a contraction of gly(cine) phos(phon)ate. The molecule has several dissociable hydrogens, especially the first hydrogen of the phosphate group. The molecule tends to exist as a zwitterion where a phosphonic hydrogen dissociates and joins the amine group. Glyphosate is soluble in water to 12 g/L at room temperature.

Main deactivation path is hydrolysis to aminomethylphosphonic acid (AMPA).

Glyphosate was first discovered to have herbicidal activity in 1970 by John E. Franz, while working for Monsanto. Franz received the National Medal of Technology in 1987 and the Perkin Medal for Applied Chemistry in 1990 for his discoveries. Franz was then inducted into the National Inventor's Hall of Fame in 2007.

Biochemistry

Glyphosate kills plants by interfering with the synthesis of the aromatic amino acids phenylalanine, tyrosine and tryptophan. It does this by inhibiting the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), which catalyzes the reaction of shikimate-3-phosphate (S3P) and phosphoenolpyruvate to form 5-enolpyruvyl-shikimate-3-phosphate (ESP).

File:EPSPreactionII.tif

ESP is subsequently dephosphorylated to chorismate, an essential precursor for the amino acids mentioned above. These amino acids are used in protein synthesis and to produce secondary metabolites such as folates, ubiquinones and naphthoquinone.

X-ray crystallographic studies of glyphosate and EPSPS show that glyphosate functions by occupying the binding site of the phosphoenolpyruvate, mimicking an intermediate state of the ternary enzyme substrates complex.

The enzyme that glyphosate inhibits, EPSPS, is found only in plants and micro-organisms. EPSPS is not present in animals, which instead obtain aromatic amino acids from their diet.

Glyphosate has also been shown to inhibit other plant enzymes, and also has been found to affect animal enzymes.

Glyphosate is absorbed through foliage. Because of this mode of action, it is only effective on actively growing plants; it is not effective in preventing seeds from germinating.

Use

Glyphosate is effective in killing a wide variety of plants, including grasses, broadleaf, and woody plants. It has a relatively small effect on some clover species. By volume, it is one of the most widely used herbicides. It is commonly used for agriculture, horticulture, viticulture and silviculture purposes, as well as garden maintenance (including home use). Prior to harvest glyphosate is used for crop desiccation (siccation) to increase the harvest yield.

In many cities, glyphosate is sprayed along the sidewalks and streets, as well as crevices in between pavement where weeds often grow. However, up to 24% of glyphosate applied to hard surfaces can be run off by water. Glyphosate contamination of surface water is highly attributed to urban use. Glyphosate is used to clear railroad tracks and get rid of unwanted aquatic vegetation.

Glyphosate is one of a number of herbicides used by the United States and Colombian governments to spray coca fields through Plan Colombia. Its effects on legal crops and effectiveness in fighting the war on drugs have been disputed. There are reports that widespread application of glyphosate in attempts to destroy coca crops in South America have resulted in the development of glyphosate-resistant strains of coca nicknamed "Boliviana Negra", which have been selectively bred to be both "Roundup Ready" and larger and higher yielding than the original strains of the plant. However, there are no reports of glyphosate-resistant coca in the peer-reviewed literature. In addition, since spraying of herbicides is not permitted in Colombian national parks, this has encouraged coca growers to move into park areas, cutting down the natural vegetation, and establishing coca plantations within park lands.

Formulations and tradenames

This section needs expansion with: examples of formulations of glyphosate – what are other surfactants and adjuvants? what are their qualities? Which are best for various purposes of farmers? What are the risks of those chemicals? There are many.. You can help by making an edit requestadding to it . (September 2012)

Glyphosate is marketed in the United States and worldwide by many agrochemical companies in different solution strengths under many tradenames: Accord, Aquaneat, Aquamaster, Bronco, Buccaneer, Campain, Clearout 41 Plus, Clear-up, Expedite, Fallow Master, Genesis Extra I, Glyfos Induce, Glypro, GlyStar Induce, GlyphoMax Induce, Honcho, JuryR, Landmaster, MirageR, Pondmaster, Protocol, Prosecutor, Ranger, Rascal, Rattler, Razor Pro, Rodeo, Roundup, I, Roundup Pro Concentrate, Roundup UltraMax, Roundup WeatherMax, Silhouette, Touchdown IQ.

Manufacturers include Bayer, Dow AgroSciences, Du Pont, Cenex/Land O’Lakes, Helena, Monsanto, Platte, Riverside/Terra, and Zeneca.

Glyphosate is an acid molecule, but it is formulated as a salt for packaging and handling. Various salt formulations include isopropylamine, diammonium, monoammonium, or potassium. Some brands include more than one salt. Some companies report their product as acid equivalent (ae) of glyphosate acid, or some report it as active ingredient (ai) of glyphosate plus the salt, and others report both. In order to compare performance of different formulations it is critical to know how the products were formulated. Since the salt does not contribute to weed control and different salts have different weights, the acid equivalent is a more accurate method of expressing, and comparing concentrations. Adjuvant loading refers to the amount of adjuvant already added to the glyphosate product. Fully loaded products contain all the necessary adjuvants, including surfactant, some contain no adjuvant system; while other products contain only a limited amount of adjuvant (minimal or partial loading) and additional surfactants must be added to the spray tank before application. As of 2000 (just before Monsanto's patent on glyphosate expired) there were 400 commercial adjuvants from over 34 different companies available for use in commercial agriculture.

Products are supplied most commonly in formulations of 120, 240, 360, 480 and 680 g active ingredient per litre. The most common formulation in agriculture is 360 g, either alone or with added cationic surfactants.

For 360 g formulations, European regulations allow applications of up to 12 litres per hectare for control of perennial weeds such as couch grass. More commonly, rates of 3 litres per hectare are practiced for control of annual weeds between crops.

Monsanto's Roundup

Monsanto developed and patented the glyphosate molecule in the 1970s, and has marketed Roundup since 1973. It retained exclusive rights in the United States until its United States patent expired in September, 2000.

As of 2009, sales of the Roundup herbicide line of products represented about 10% of Monsanto's revenue due to competition from other producers of other glyphosate-based herbicides; the overall Roundup line of products (which includes GM seeds) represents about half of Monsanto's yearly revenue.

The active ingredient of Roundup is the isopropylamine salt of glyphosate. Another important ingredient in some formulations of Roundup is the surfactant POEA (polyethoxylated tallow amine), which has been found to be highly toxic to animals and to humans.

Monsanto also produces seeds which grow into plants genetically engineered to be tolerant to glyphosate, which are known as Roundup Ready crops. The genes contained in these seeds are patented. Such crops allow farmers to use glyphosate as a post-emergence herbicide against most broadleaf and cereal weeds. Soy was the first Roundup Ready crop, and was produced at Monsanto's Agracetus Campus located in Middleton, Wisconsin.

In November 2009, a French environment group (MDRGF) accused Monsanto of using chemicals in Roundup formulations not disclosed to the country's regulatory bodies, and demanded the removal of those products from the market.

Toxicity

Glyphosate is the active ingredient in herbicide formulations containing it. However, in addition to glyphosate salts, commercial formulations of glyphosate contain additives such as surfactants which vary in nature and concentration. Laboratory toxicology studies have suggested that other ingredients in combination with glyphosate may have greater toxicity than glyphosate alone. Toxicologists have studied glyphosate alone, additives alone, and formulations.

Glyphosate toxicity

Glyphosate has a United States Environmental Protection Agency (EPA) Toxicity Class of III (on a I to IV scale, where IV is least dangerous) for oral and inhalation exposure. Nonetheless, as with other herbicides, the EPA requires that products containing glyphosate carry a label that warns against oral intake, mandates the use of protective clothing, and instructs users not to re-enter treated fields for at least 4 hours. Glyphosate does not bioaccumulate and breaks down rapidly in the environment. It is excreted in urine and faeces. Health, environmental and food chain effects from alteration of gut flora by wide use of glyphosate are largely unexplored.

Human

Based on an assessment completed in 1993 and published as a Reregistration Eligibility Decision (RED) document, the EPA considers glyphosate to be noncarcinogenic and relatively low in dermal and oral acute toxicity. The EPA considered a "worst case" dietary risk model of an individual eating a lifetime of food derived entirely from glyphosate-sprayed fields with residues at their maximum levels. This model indicated that no adverse health effects would be expected under such conditions. No mention of consideration of potential alteration of human gut flora as it does in other species and its public health implications to humans directly or via the plant animal human food chain was mentioned in the summary.

Human toxicity is dose related. Acute fatal toxicity has been reported in deliberate overdose.

Effects on fish and amphibians

Glyphosate is generally less persistent in water than in soil, with 12 to 60 day persistence observed in Canadian pond water, yet because glyphosate binds to soil, persistence of over a year has been observed in the sediments of ponds in Michigan and Oregon. In streams, maximum glyphosate concentrations were measured immediately post-treatment and dissipated rapidly. Glyphosate is "practically nontoxic to slightly toxic" for amphibians and fish.

Soil degradation, and effects on micro-organism and worms

When glyphosate comes into contact with the soil, it can be rapidly bound to soil particles and be inactivated. Unbound glyphosate can be degraded by bacteria.

In soils, half-lives vary from as little as three days at a site in Texas to 141 days at a site in Iowa. In addition, the glyphosate metabolite aminomethylphosphonic acid has been found in Swedish forest soils up to two years after a glyphosate application. Glyphosate adsorption to soil varies depending on the kind of soil.

It has been suggested that glyphosate can harm the bacterial ecology of soil and cause micronutrient deficiencies in plants, including nitrogen-fixing bacteria. A 2012 study found that while Roundup had toxic effects at low levels on three food microorganisms (e.g. Lactobacillus delbrueckii), "glyphosate at these levels has no significant effect".

Additive toxicity

This section needs expansion. You can help by making an edit requestadding to it . (September 2012)

Polyethoxylated tallow amine

A review of the literature provided to the EPA in 1997 found that polyethoxylated tallow amine (POEA) was more toxic to fish than glyphosate.

Formulation Toxicity

Human

Data from the California Environmental Protection Agency's Pesticide Illness Surveillance Program, which also tracks other agricultural chemicals, shows that glyphosate-related incidents are some of the most common. However, incident counts alone do not take into account the number of people exposed and the severity of symptoms associated with each incident. For example, if hospitalization were used as a measure of the severity of incidents, then glyphosate would be considered relatively safe; over a 13-year period in California, none of the 515 reported hospitalizations were attributed to glyphosate.

Deliberate ingestion of Roundup in quantities ranging from 85 to 200 ml has resulted in death within hours of ingestion, although it has also been ingested in quantities as large as 500 ml with only mild or moderate symptoms. There is a reasonable correlation between the amount of Roundup ingested and the likelihood of serious systemic sequelae or death. Ingestion of >85 ml of the concentrated formulation is likely to cause significant toxicity in adults. Corrosive effects – 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 edema, infiltration on chest x-ray, shock, arrythmias, renal failure requiring haemodialysis, metabolic acidosis, and hyperkalaemia may occur in severe cases. Bradycardia and ventricular arrhythmias often present prior to death.

Dermal exposure to ready-to-use glyphosate formulations can cause irritation, and photo-contact dermatitis has been occasionally reported. These effects are probably due to the preservative Proxel (benzisothiazolin-3-one). Inhalation is a minor route of exposure, but spray mist may cause oral or nasal discomfort, an unpleasant taste in the mouth, or tingling and irritation in the throat. Eye exposure may lead to mild conjunctivitis. Superficial corneal injury is possible if irrigation is delayed or inadequate.

In vitro studies on human cells

A 2000 review concluded that "under present and expected conditions of new use, there is no potential for Roundup herbicide to pose a health risk to humans". A 2002 review by the European Union reached the same conclusion.

Glyphosate causes oxidative damage to human skin cells. Antioxidants such as vitamins C and E were found by one study to provide some protection against such damage, leading the authors to recommend that these chemicals be added to glyphosate formulations. Severe skin burns are very rare.

Endocrine disruption

A study published in 2000 found that Roundup interfered with an enzyme involved in testosterone production in mouse cell culture. A study by the Seralini lab published in 2005 found that glyphosate interferes with aromatase, an estrogen biosynthesis enzyme, in cultures of human placental cells and that the Roundup formulation of glyphosate had stronger such activity. A follow up study by the Seralini lab, published in 2009, showed similar results in human liver cells. A study on rats published in 2010 found that administering Roundup Transorb orally to prepubescent rats at a dose of 0.25 mL/100 g of body weight, once a day for 30 days, reduced testosterone production and affected testicle morphology, but did not affect levels of estradiol and corticosterone.

Monsanto has responded, saying that (a) Roundup formulations do contain surfactants (detergents) to help the active ingredient penetrate the waxy cuticle of the plant. (b) The surfactants are indeed more toxic than the glyphosate. (c) "If you put a detergent of any sort on cells in a petri dish, the cells get sick (and will die if you get the concentration high enough or recover if you remove the detergent soon enough)"; (d) the cell types chosen in these studies and the parameters measured were selected more to score political points than to help fully describe the risks of glyphosate and surfactants; (e) the experiments are artificial and not helpful – no one is supposed to drink Roundup, and it is not ever put on naked cells (we all have skin and workers are meant to wear protective clothes).

In 2007, the EPA selected glyphosate for further screening through its Endocrine Disruptor Screening Program. Selection for this program is based on a compound's prevalence of use and does not imply particular suspicion of endocrine activity.

Genetic damage

A 2009 study on mice found that a single intraperitoneal injection of Roundup in concentration of 25 mg/kg caused chromosomal aberrations and induction of the micronuclei.

Other mammals

A review of the ecotoxicological data on Roundup shows there are at least 58 studies of the effects of Roundup itself on a range of organisms. This review concluded that "for terrestrial uses of Roundup minimal acute and chronic risk was predicted for potentially exposed non-target organisms".

In a 2001, three groups of pregnant rats were fed, respectively, a regular diet with clean water, a regular diet with 0.2 ml glyphosate/ml drinking water; and a regular diet with 0.4 ml glyphosate/ml drinking water. Glyphosate induces a variety of functional abnormalities in fetuses and pregnant rats. Also in recent mammalian research, glyphosate has been found to interfere with an enzyme involved testosterone production in mouse cell culture.

Glyphosate is low in toxicity to rats when ingested by rats. The acute oral LD50 in rats is greater than 4320 mg/kg. Rats and mice were fed a diet containing 0, 3125, 6250, 12,500, 25,000, or 50,000 ppm of 99% pure glyphosate for 13 weeks. The two highest dose groups of male rats had a significant reduction in sperm concentrations, although concentrations were still within the historical range for that rat strain. The highest dose group of female rats had a slightly longer estrus cycle than the control group. The Reference Dose for glyphosate set by the EPA is 1.75 mg/kg/day and the maximum contaminant level set by the EPA is 0.7 mg/L

The EPA, the EC Health and Consumer Protection Directorate, and the UN World Health Organization have all concluded pure glyphosate is not carcinogenic. Opponents of glyphosate claim Roundup has been found to cause genetic damage, citing Peluso et al. The authors concluded the damage was "not related to the active ingredient, but to another component of the herbicide mixture".

Mammal research indicates oral intake of 1% glyphosate induces changes in liver enzyme activities in pregnant rats and their fetuses.

Laboratory studies have shown teratogenic effects of Roundup in animals. These reports have proposed that the teratogenic effects are caused by impaired retinoic acid signaling. News reports have supposed that regulators have been aware of these studies since 1980.

Effects on fish and amphibians

A study of various formulations of glyphosate found that "risk assessments based on estimated and measured concentrations of glyphosate that would result from its use for the control of undesirable plants in wetlands and over-water situations showed that the risk to aquatic organisms is negligible or small at application rates less than 4 kg/ha and only slightly greater at application rates of 8 kg/ha.".

Glyphosate formulations are much more toxic for amphibians and fish than glyphosate alone. "Aquaculture, freshwater and marine fisheries supply about 10% of world human calorie intake." A study published in 2010 proposed commercial glyphosate can cause neural defects and craniofacial malformations in African clawed frogs (Xenopus laevis). The experiments used frog embryos that were incubated with 1:5000 dilutions of a commercial glyphosate solution. The frog embryos suffered diminution of body size, alterations of brain morphology, reduction of the eyes, alterations of the branchial arches and otic placodes, alterations of the neural plate, and other abnormalities of the nervous system. The authors suggested glyphosate itself was responsible for the observed results because injection of pure glyphosate produced similar results in a chicken model.

Because of this known toxicity, only some formulations of glyphosate are registered for use in aquatic applications. Monsanto and other companies produce glyphosate products with alternative surfactants that are specifically formulated for aquatic use, for example "Biactive" and "AquaMaster". The glyphosate formulations registered for aquatic use have been found to have negligible adverse effects on sensitive amphibians.

Soil degradation and effects on micro-organism and worms

A laboratory study published in 1992 indicated that glyphosate formulations could harm earthworms and beneficial insects. However, the reported effect of glyphosate on earthworms has been criticized. The results conflict with results from field studies where no effects were noted for the number of nematodes, mites, or springtails after treatment with Roundup at 2 kilograms active ingredient per hectare.

A 2009 study using a RoundUp formulation has concluded that absorption into plants delays subsequent soil-degradation, and can increase glyphosate persistence in soil from two to six times.

Effect on plant health

A study published in 2005 found a correlation between an increase in the infection rate of wheat by fusarium head blight and the application of glyphosate, but the authors wrote: "because of the nature of this study, we could not determine if the association between previous GF (glyphosate formulation) use and FHB development was a cause-effect relationship". Other studies have found causal relationships between glyphosate and decreased disease resistance.

Resistance in weeds and microorganisms

Resistance evolves after a weed population has been subjected to intense selection pressure in the form of repeated use of a single herbicide. The first documented cases of weed resistance to glyphosate were found in Australia in 1996, involving rigid ryegrass (Lolium rigidum) near Orange, New South Wales. Weeds resistant to the herbicide have been called superweeds. As of 2010, in the United States 7 to 10 million acres (40,000 km) of soil was afflicted by those superweeds, or about 5% of the 170 million acres planted with corn, soybeans and cotton, the crops most affected, in 22 states. In 2006, farmers associations were reporting 103 biotypes of weeds within 63 weed species with herbicide resistance. In 2009, Canada identified its first resistant weed, giant ragweed, and at that time fifteen weed species had been confirmed as resistant to glyphosate.

In response, farmers are hand-weeding, using tractors to turn over soil between crops, and using other herbicides in addition to glyphosate. Agricultural biotech companies are also developing genetically engineered crops resistant to other herbicides. "Bayer is already selling cotton and soybeans resistant to glufosinate, another weedkiller. Monsanto's newest corn is tolerant of both glyphosate and glufosinate, and the company is developing crops resistant to dicamba, an older pesticide. Syngenta is developing soybeans tolerant of its Callisto product. And Dow Chemical is developing corn and soybeans resistant to 2,4-D, a component of Agent Orange, the defoliant used in the Vietnam War."

Palmer amaranth

In 2004, a glyphosate-resistant variation of Palmer amaranth, commonly known as pigweed, was found in Georgia and confirmed by a 2005 study. In 2005, resistance was also found in North Carolina. Widespread use of Roundup Ready crops led to an unprecedented selection pressure and glyphosate resistance followed. The weed variation is now widespread in the southeastern United States. Cases have also been reported in Texas and Virginia.

Conyza

Conyza bonariensis (also known as hairy fleabane and buva) and Conyza canadensis (known as horseweed or marestail), are other weed species that had lately developed glyphosate resistance. A 2008 study on the current situation of glyphosate resistance in South America concluded that "resistance evolution followed intense glyphosate use" and the utilization of glyphosate-resistant soybean crops is a factor encouraging increase in glyphosate use.

Ryegrass

Glyphosate resistant ryegrass (Lolium) has occurred in most of the Australian agricultural area and other areas of the world. All cases of evolution of resistance to glyphosate in Australia were characterized by intensive use of the herbicide while no other effective weed control practices were used. Studies indicate that resistant ryegrass does not compete well against non-resistant plants and their numbers decrease when not grown under conditions of glyphosate application.

Johnson grass

Glyphosate-resistant Johnson grass (Sorghum halepense) has occurred in glyphosate-resistant soybean culture in Argentina.

Coca

Boliviana negra, also known as "supercoca", is a relatively new strain of coca that is resistant to glyphosate, which is a key ingredient in the multibillion-dollar aerial coca eradication campaign undertaken by the government of Colombia with United States financial and military backing known as Plan Colombia. Spraying Boliviana negra with glyphosate would serve to strengthen its growth by eliminating the non-resistant weeds surrounding it. Joshua Davis, writing in Wired magazine, found no evidence of CP4 EPSPS, a protein produced by the Roundup Ready soybean, suggesting Bolivana negra was not created in a laboratory but by selective breeding in the fields. According to Davis, the growing popularity of Boliviana negra amongst growers could have serious repercussions for the United States war on drugs.

Legal cases

False advertising

The New York Times reported that in 1996, "Dennis C. Vacco, the Attorney General of New York, ordered the company to pull ads that said Roundup was "safer than table salt" and "practically nontoxic" to mammals, birds and fish. The company withdrew the spots, but also said that the phrase in question was permissible under E.P.A. guidelines."

On Fri Jan 20, 2007, Monsanto was convicted in France of false advertising of Roundup for presenting it as biodegradable, and claiming it left the soil clean after use. Environmental and consumer rights campaigners brought the case in 2001 on the basis that glyphosate, Roundup's main ingredient, is classed as "dangerous for the environment" and "toxic for aquatic organisms" by the European Union. Monsanto appealed and the court upheld the verdict; Monsanto appealed again to the French Supreme Court, and in 2009 it also upheld the verdict.

Scientific fraud

On two occasions, the United States EPA has caught scientists deliberately falsifying test results at research laboratories hired by Monsanto to study glyphosate. The first incident involved Industrial Biotest Laboratories (IBT). The United States Justice Department closed the laboratory in 1978, and its leadership was found guilty in 1983 of charges of falsifying statements, falsifying scientific data submitted to the government, and mail fraud. In 1991, Don Craven, the owner of Craven Laboratories and three employees were indicted on 20 felony counts. Craven, along with fourteen employees were found guilty of similar crimes.

Monsanto has stated the Craven Labs investigation was started by the EPA after a pesticide industry task force discovered irregularities, that the studies have been repeated, and that Roundup's EPA certification does not now use any studies from Craven Labs or IBT.

Trade dumping allegations

United States companies have cited trade issues with glyphosate being dumped into the western world market areas by Chinese companies and a formal dispute was filed in 2010.

Genetically modified crops

Some micro-organisms have a version of 5-enolpyruvoyl-shikimate-3-phosphate synthetase (EPSPS) that is resistant to glyphosate inhibition. The version used in the initial round of genetically modified crops was isolated from Agrobacterium strain CP4 (CP4 EPSPS) that was resistant to glyphosate. This CP4 EPSPS gene was cloned and transfected into soybeans.

In 1996, genetically modified soybeans were made commercially available. Current glyphosate-resistant crops include soy, maize (corn), sorghum, canola, alfalfa, and cotton, with wheat still under development.

Genetically modified crops have become the norm in the United States. For example, in 2010, 70% of all the corn that was planted was herbicide-resistant; 78% of cotton, and 93% of all soybeans.

See also

• Environmental impact of pesticides
• Health effects of pesticides
• 2,4-Dichlorophenoxyacetic acid
• Atrazine
• Integrated pest management

References

1. ^ Glyphosate, Environmental Health Criteria monograph No. 159, Geneva: World Health Organization, 1994, ISBN 92-4-157159-4
2. Index no. 607-315-00-8 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. Official Journal of the European Union L353, 31 December 2008, pp. 1–1355 at pp 570, 1100..
3. US Patent 3,799,758
4. Stephen O Duke and Stephen B. Powles (2008) Glyphosate: a once-in-a-century herbicide: Mini-review. Pest Management Science Pest Manag Sci 64:319–325
5. United States EPA 2007 Pesticide Market Estimates Agriculture, Home and Garden
6. Graves, Lucia (24 June 2011). "Roundup: Birth Defects Caused By World's Top-Selling Weedkiller, Scientists Say". Huffington Post.
7. Environmental Fate of Glyphosate, Jeff Schuette, Department of Pesticide Regulation, California
8. Alibhai, Murtaza F.; Stallings, William C. (2001). "Closing down on glyphosate inhibition – with a new structure for drug discovery". Proceedings of the National Academy of Sciences. 98 (6): 2944–6. Bibcode:2001PNAS...98.2944A. doi:10.1073/pnas.061025898. JSTOR 3055165. PMC 33334. PMID 11248008.
9. United States Patent and Trademark Office Official Website The National Medal of Technology and Innovation Recipients – 1987 Accessed November 29, 2012
10. "People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry". The Scientist. 4 (10): 28. 1990.
11. Inventor's Hall Of Fame Official Website, Inductees for 2007
12. Steinrücken, H.C.; Amrhein, N. (1980). "The herbicide glyphosate is a potent inhibitor of 5-enolpyruvylshikimic acid-3-phosphate synthase". Biochemical and Biophysical Research Communications. 94 (4): 1207–12. doi:10.1016/0006-291X(80)90547-1. PMID 7396959.
13. Purdue University, Department of Horticulture and Landscape Architecture, Metabolic Plant Physiology Lecture notes, Aromatic amino acid biosynthesis, The shikimate pathway – synthesis of chorismate.
14. Schonbrunn, Ernst; Eschenburg, Susanne; Shuttleworth, Wendy A.; Schloss, John V.; Amrhein, Nikolaus; Evans, Jeremy N. S.; Kabsch, Wolfgang (2001). "Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail". Proceedings of the National Academy of Sciences. 98 (4): 1376–80. Bibcode:2001PNAS...98.1376S. doi:10.1073/pnas.98.4.1376. JSTOR 3054883. PMC 29264. PMID 11171958.
15. Glyphosate bound to proteins in the Protein Data Bank
16. Funke, Todd; Han, Huijong; Healy-Fried, Martha L.; Fischer, Markus; Schönbrunn, Ernst (2006). "Molecular basis for the herbicide resistance of Roundup Ready crops". Proceedings of the National Academy of Sciences. 103 (35): 13010–5. Bibcode:2006PNAS..10313010F. doi:10.1073/pnas.0603638103. JSTOR 30050705. PMC 1559744. PMID 16916934.
17. Su, Ling Yuan; Dela Cruz, Amy; Moore, Paul H.; Maretzki, Andrew (1992). "The Relationship of Glyphosate Treatment to Sugar Metabolism in Sugarcane: New Physiological Insights". Journal of Plant Physiology. 140 (2): 168. doi:10.1016/S0176-1617(11)80929-6.
18. Lamb, D.C.; Kelly, D.E.; Hanley, S.Z.; Mehmood, Z.; Kelly, S.L. (1998). "Glyphosate is an Inhibitor of Plant Cytochrome P450: Functional Expression of Thlaspi arvensae Cytochrome P45071B1/Reductase Fusion Protein inEscherichia coli". Biochemical and Biophysical Research Communications. 244 (1): 110–4. doi:10.1006/bbrc.1997.7988. PMID 9514851.
19. Hietanen, Eino; Linnainmaa, Kaija; Vainio, Harri (2009). "Effects of Phenoxyherbicides and Glyphosate on the Hepatic and Intestinal Biotransformation Activities in the Rat". Acta Pharmacologica et Toxicologica. 53 (2): 103–12. doi:10.1111/j.1600-0773.1983.tb01876.x. PMID 6624478.
20. Integrated Pest Management
21. ^ National Pesticide Information Center Technical Factsheet on: GLYPHOSATE
22. Thomas M Amrein (12/21/2012). "Analysis of pesticides in food" (PDF). ETH Zurich. p. 15. Retrieved 06/02/2013. {{cite web}}: Check date values in: |accessdate= and |date= (help)
23. ^ "The agronomic benefits of glyphosate in Europe" (PDF). Monsanto Europe SA. February 2010. Retrieved 06/02/2013. {{cite web}}: Check date values in: |accessdate= (help)
24. Measures to reduce glyphosate runoff from hard surfaces
25. Botta, Fabrizio; Lavison, Gwenaëlle; Couturier, Guillaume; Alliot, Fabrice; Moreau-Guigon, Elodie; Fauchon, Nils; Guery, Bénédicte; Chevreuil, Marc; Blanchoud, Hélène (2009). "Transfer of glyphosate and its degradate AMPA to surface waters through urban sewerage systems". Chemosphere. 77 (1): 133–9. doi:10.1016/j.chemosphere.2009.05.008. PMID 19482331.
26. Plan Colombia
27. Jeremy McDermott. The Scotsman (Scotland) 27 August 2004 New Super Strain of Coca Plant Stuns Anti-Drug Officials
28. Chris Kraul for the Los Angeles Times. February 25, 2008 Picture a natural disaster wrought by drug trade
29. Mirror or Mirror on the Wall Show Me the Best Glyphosate Formulation of All. Wayne Mitchem, North Carolina State University Extension
30. Glyphosate – A Review. Bob Hartzler Iowa State University Extension
31. California Product/Label Database
32. ^ M. Tu, C. Hurd, R. Robison & J.M. Randall. Glyphosate. Weed Control Methods Handbook, The Nature Conservancy
33. ^ Glyphosate Formulations Mark VanGessel, Extension Weed Specialist. University of Delaware Cooperative Extension
34. Tu et al .Weed Control Methods Handbook, Chapter 8, Adjuvants The Nature Conservancy, June 2003.
35. W. S. Curran, M. D. McGlamery, R. A. Liebl, and D. D. Lingenfelter. 1999. Penn State Extension Service. Adjuvants for Enhancing Herbicide Performance
36. Christy Sprague and Aaron Hager for University of Illinois Extension Service. May 12, 2000. Principles of Postemergence Herbicides Accessed November 29, 2012
37. Bryan Young, Southern Illinois University Compendium of Herbicide Adjuvants: Adjuvant Company Contact Information
38. e-phy: Le catalogue des produits phytopharmaceutiques et de leurs usages des matières fertilisantes et des supports de culture homologués en France
39. "The debate over whether Monsanto is a corporate sinner or saint". The Economist. 19 November 2009. Retrieved 20 November 2009.
40. Cavallaro, Matt (2009-06-26). "The Seeds Of A Monsanto Short Play". Forbes. Retrieved 2009-07-11.
41. Altieri, M. A. (2009). "The Ecological Impacts of Large-Scale Agrofuel Monoculture Production Systems in the Americas". Bulletin of Science, Technology & Society. 29 (3): 236. doi:10.1177/0270467609333728.
42. Benachour, Nora; SéRalini, Gilles-Eric (2009). "Glyphosate Formulations Induce Apoptosis and Necrosis in Human Umbilical, Embryonic, and Placental Cells". Chemical Research in Toxicology. 22 (1): 97–105. doi:10.1021/tx800218n. PMID 19105591.
43. Hedberg, Daniel; Wallin, Margareta (2010). "Effects of Roundup and glyphosate formulations on intracellular transport, microtubules and actin filaments in Xenopus laevis melanophores". Toxicology in Vitro. 24 (3): 795–802. doi:10.1016/j.tiv.2009.12.020. PMID 20036731.
44. Zeliger, Harold I. (2008). Human Toxicology of Chemical Mixtures. William Andrew. p. 388. ISBN 978-0-8155-1589-0.
45. "Round up: une association veut le retrait". Le Figaro (in French). 2009-11-18. Retrieved 19 November 2009.
46. "Dossier de presse – alerte pesticides: le cas de 3 Roundup" (PDF) (in French). Mouvement pour les droits et le respect des générations futures (MDRGF). 1 November 2009. Retrieved 19 November 2009.
47. ^ Bradberry, Sally M; Proudfoot, Alex T; Vale, J Allister (2004). "Glyphosate Poisoning". Toxicological Reviews. 23 (3): 159–67. PMID 15862083.
48. ^ U.S. EPA ReRegistration Decision Fact Sheet for Glyphosate (EPA-738-F-93-011) 1993. Cite error: The named reference "epa_reds" was defined multiple times with different content (see the help page).
49. Sample label – Roundup Pro
50. Gary Williams, Robert Kroes, and Ian Munro. Updated May, 2005. Backgrounder: Summary of Human Risk Assessment and Safety Evaluation on Glyphosate and Roundup Herbicide
51. Krüger, Monika (NaN undefined NaN). "Glyphosate suppresses the antagonistic effect of Enterococcus spp. on Clostridium botulinum". Anaerobe. 20: 74–78. doi:10.1016/j.anaerobe.2013.01.005. {{cite journal}}: Check date values in: |date= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
52. Shehata, Awad A. (NaN undefined NaN). "The Effect of Glyphosate on Potential Pathogens and Beneficial Members of Poultry Microbiota In Vitro". Current Microbiology. 66 (4): 350–358. doi:10.1007/s00284-012-0277-2. {{cite journal}}: Check date values in: |date= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
53. Arregui, MC (2004 Feb). "Monitoring glyphosate residues in transgenic glyphosate-resistant soybean". Pest management science. 60 (2): 163–6. PMID 14971683. {{cite journal}}: Check date values in: |date= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
54. Sribanditmongkol, Pongruk (1 September 2012). "Pathological and Toxicological Findings in Glyphosate-Surfactant Herbicide Fatality". The American Journal of Forensic Medicine and Pathology. 33 (3): 234–237. doi:10.1097/PAF.0b013e31824b936c. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
55. Bradberry, SM (2004). "Glyphosate poisoning". Toxicological reviews. 23 (3): 159–67. PMID 15862083. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
56. ^ Giesy, John P.; Dobson, Stuart; Solomon, Keith R. (2000). "Ecotoxicological Risk Assessment for Roundup® Herbicide". Reviews of Environmental Contamination and Toxicology. Reviews of Environmental Contamination and Toxicology. 167: 35–120. doi:10.1007/978-1-4612-1156-3_2. ISBN 978-0-387-95102-7.
57. ^ Andréa, Mara Mercedes de; Peres, Terezinha Bonanho; Luchini, Luiz Carlos; Bazarin, Sheila; Papini, Solange; Matallo, Marcus Barifouse; Savoy, Vera Lucia Tedeschi (2003). "Influence of repeated applications of glyphosate on its persistence and soil bioactivity". Pesquisa Agropecuária Brasileira. 38 (11): 1329. doi:10.1590/S0100-204X2003001100012.
58. Balthazor, Terry M.; Hallas, Laurence E. (1986). "Glyphosate-Degrading Microorganisms from Industrial Activated Sludge". Applied and Environmental Microbiology. 51 (2): 432–4. PMC 238888. PMID 16346999.
59. Torstensson, NT; Lundgren, LN; Stenström, J (1989). "Influence of climatic and edaphic factors on persistence of glyphosate and 2,4-D in forest soils". Ecotoxicology and Environmental Safety. 18 (2): 230–9. doi:10.1016/0147-6513(89)90084-5. PMID 2806176.
60. Albers, Christian N.; Banta, Gary T.; Hansen, Poul Erik; Jacobsen, Ole S. (2009). "The influence of organic matter on sorption and fate of glyphosate in soil – Comparing different soils and humic substances". Environmental Pollution. 157 (10): 2865–70. doi:10.1016/j.envpol.2009.04.004. PMID 19447533.
61. Dick, Richard; Lorenz, Nicola; Wojno, Michal; Lane, Matt (2010). "Microbial dynamics in soils under long-term glyphosate tolerant cropping systems" (PDF). 19th World Congress of Soil Science.
62. Santos, A.; Flores, M. (1995). "Effects of glyphosate on nitrogen fixation of free-living heterotrophic bacteria". Letters in Applied Microbiology. 20 (6): 349–52. doi:10.1111/j.1472-765X.1995.tb01318.x.
63. Clair E, Linn L, Travert C, Amiel C, Séralini GE, Panoff JM. Effects of Roundup(®) and glyphosate on three food microorganisms: Geotrichum candidum, Lactococcus lactis subsp. cremoris and Lactobacillus delbrueckii subsp. bulgaricus. Curr Microbiol. 2012 May;64(5):486-91. doi: 10.1007/s00284-012-0098-3. pmid: 22362186
64. Gary L. Diamond and Patrick R. Durkin February 6, 1997, under contract from the United States Department of Agriculture. Effects of Surfactants on the Toxicitiy of Glyphosate, with Specific Reference to RODEO
65. Goldstein, Daniel A.; Acquavella, John F.; Mannion, Rhonda M.; Farmer, Donna R. (2002). "An Analysis of Glyphosate Data from the California Environmental Protection Agency Pesticide Illness Surveillance Program". Clinical Toxicology. 40 (7): 885–92. doi:10.1081/CLT-120016960. PMID 12507058.
66. ^ California EPA 1996, California Pesticide Illness Serveillance Program Report HS-1733
67. Talbot, Alan Ronald; Shiaw, Mon-Han; Huang, Jinn-Sheng; Yang, Shu-Fen; Goo, Tein-Shong; Wang, Shur-Hueih; Chen, Chao-Liang; Sanford, Thomas Richard (1991). "Acute Poisoning with a Glyphosate-Surfactant Herbicide ('Roundup'): A Review of 93 Cases". Human & Experimental Toxicology. 10 (1): 1–8. doi:10.1177/096032719101000101. PMID 1673618.
68. Williams, Gary M.; Kroes, Robert; Munro, Ian C. (2000). "Safety Evaluation and Risk Assessment of the Herbicide Roundup and Its Active Ingredient, Glyphosate, for Humans". Regulatory Toxicology and Pharmacology. 31 (2): 117–65. doi:10.1006/rtph.1999.1371. PMID 10854122.
69. Review report for the active substance glyphosate
70. Gehin, Audrey; Guillaume, Yves Claude; Millet, Joëlle; Guyon, Catherine; Nicod, Laurence (2005). "Vitamins C and E reverse effect of herbicide-induced toxicity on human epidermal cells HaCaT: A biochemometric approach". International Journal of Pharmaceutics. 288 (2): 219–26. doi:10.1016/j.ijpharm.2004.09.024. PMID 15620861.
71. ^ Walsh, LP; McCormick, C; Martin, C; Stocco, DM (2000). "Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (StAR) protein expression". Environmental health perspectives. 108 (8): 769–76. doi:10.1289/ehp.00108769. PMC 1638308. PMID 10964798. Cite error: The named reference "walsh" was defined multiple times with different content (see the help page).
72. Richard, Sophie; Moslemi, Safa; Sipahutar, Herbert; Benachour, Nora; Seralini, Gilles-Eric (2005). "Differential Effects of Glyphosate and Roundup on Human Placental Cells and Aromatase". Environmental Health Perspectives. 113 (6): 716–20. doi:10.1289/ehp.7728. PMC 1257596. PMID 15929894.
73. Gasnier, Céline; Dumont, Coralie; Benachour, Nora; Clair, Emilie; Chagnon, Marie-Christine; Séralini, Gilles-Eric (2009). "Glyphosate-based herbicides are toxic and endocrine disruptors in human cell lines". Toxicology. 262 (3): 184–91. doi:10.1016/j.tox.2009.06.006. PMID 19539684.
74. Romano, R. M.; Romano, M. A.; Bernardi, M. M.; Furtado, P. V.; Oliveira, C. A. (2009). "Prepubertal exposure to commercial formulation of the herbicide glyphosate alters testosterone levels and testicular morphology". Archives of Toxicology. 84 (4): 309–17. doi:10.1007/s00204-009-0494-z. PMID 20012598.
75. Monsantoblog: The Skinny on the Seralini Safety Study 2009/06/23
76. EPA Federal Register http://www.epa.gov/endo/pubs/draft_list_frn_061807.pdf
77. Prasad, Sahdeo; Srivastava, Smita; Singh, Madhulika; Shukla, Yogeshwer (2009). "Clastogenic Effects of Glyphosate in Bone Marrow Cells of Swiss Albino Mice". Journal of Toxicology. 2009: 1. doi:10.1155/2009/308985.{{cite journal}}: CS1 maint: unflagged free DOI (link)
78. Daruich, J; Zirulnik, F; Gimenez, MS (2001). "Effect of the Herbicide Glyphosate on Enzymatic Activity in Pregnant Rats and Their Fetuses". Environmental Research. 85 (3): 226–31. doi:10.1006/enrs.2000.4229. PMID 11237511.
79. Roundup PRO Herbicide MSDS
80. United States EPA Reregistration Eligibility Decision – Glyphosate
81. Peluso, Marco; Munnia, Armelle; Bolognesi, Claudia; Parodi, Silvio (1998). "32P-postlabeling detection of DNA adducts in mice treated with the herbicide roundup". Environmental and Molecular Mutagenesis. 31 (1): 55–9. doi:10.1002/(SICI)1098-2280(1998)31:1<55::AID-EM8>3.0.CO;2-A. PMID 9464316.
82. Daruich, Jorgelina; Zirulnik, Fanny; Giménez, María Sofía (2001). "Effect of the Herbicide Glyphosate on Enzymatic Activity in Pregnant Rats and Their Fetuses". Environmental Research. 85 (3): 226–31. doi:10.1006/enrs.2000.4229. PMID 11237511.
83. Lammer, Edward J.; Chen, Diane T.; Hoar, Richard M.; Agnish, Narsingh D.; Benke, Paul J.; Braun, John T.; Curry, Cynthia J.; Fernhoff, Paul M.; Grix, Art W. (1985). "Retinoic Acid Embryopathy". New England Journal of Medicine. 313 (14): 837–41. doi:10.1056/NEJM198510033131401. PMID 3162101.
84. Durston, A. J.; Timmermans, J. P. M.; Hage, W. J.; Hendriks, H. F. J.; De Vries, N. J.; Heideveld, M.; Nieuwkoop, P. D. (1989). "Retinoic acid causes an anteroposterior transformation in the developing central nervous system". Nature. 340 (6229): 140–4. doi:10.1038/340140a0. PMID 2739735.
85. ^ Paganelli, Alejandra; Gnazzo, Victoria; Acosta, Helena; López, Silvia L.; Carrasco, Andrés E. (2010). "Glyphosate-Based Herbicides Produce Teratogenic Effects on Vertebrates by Impairing Retinoic Acid Signaling". Chemical Research in Toxicology. 23 (10): 1586. doi:10.1021/tx1001749. PMID 20695457.
86. Graves, Lucia (7 June 2011). "Roundup Birth Defects: Regulators Knew World's Best-Selling Herbicide Causes Problems, New Report Finds". Huffington Post. Retrieved 9 June 2011.
87. Solomon, Keith; Thompson, Dean (2003). "Ecological Risk Assessment for Aquatic Organisms from Over-Water Uses of Glyphosate". Journal of Toxicology and Environmental Health, Part B. 6 (3): 289–324. doi:10.1080/10937400306468. PMID 12746143.
88. Salbego, Joseânia; Pretto, Alexandra; Gioda, Carolina Rosa; Menezes, Charlene Cavalheiro; Lazzari, Rafael; Radünz Neto, João; Baldisserotto, Bernardo; Loro, Vania Lucia (2010). "Herbicide Formulation with Glyphosate Affects Growth, Acetylcholinesterase Activity, and Metabolic and Hematological Parameters in Piava (Leporinus obtusidens)". Archives of Environmental Contamination and Toxicology. 58 (3): 740–5. doi:10.1007/s00244-009-9464-y. PMID 20112104.
89. Relyea, Rick A. (2005). "The Impact of Insecticides and Herbicides on the Biodiversity and Productivity of Aquatic Communities". Ecological Applications. 15 (2): 618–27. doi:10.1890/03-5342. JSTOR 4543379.
90. World Food Supply UNEP (www.grida.no)
91. Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities", Monsanto Corporation Backgrounder
92. Chivian, Eric; Bernstein, Aaron (2008). "Threatened Groups of Organisms Valuable to Medicine". In Eric Chivian (ed.). Sustaining Life: How Human Health Depends on Biodiversity. Oxford University Press, USA. p. 209. ISBN 978-0-19-517509-7.
93. Aquatic Use of Glyphosate Herbicides in Australia, Monsanto Corporation Backgrounder
94. Wojtaszek, Barbara F.; Staznik, Bozena; Chartrand, Derek T.; Stephenson, Gerald R.; Thompson, Dean G. (2004). "Effects of Vision® Herbicide on Mortality, Avoidance Response, and Growth of Amphibian Larvae in Two Forest Wetlands". Environmental Toxicology and Chemistry. 23 (4): 832–42. doi:10.1897/02-281. PMID 15095877.
95. Springett, J.A.; Gray, R.A.J. (1992). "Effect of repeated low doses of biocides on the earthworm Aporrectodea caliginosa in laboratory culture". Soil Biology and Biochemistry. 24 (12): 1739. doi:10.1016/0038-0717(92)90180-6.
96. Hassan, S. A.; Bigler, F.; Bogenschütz, H.; Boller, E.; Brun, J.; Calis, J. N. M.; Chiverton, P.; Coremans-Pelseneer, J.; Duso, C. (1991). "Results of the fifth joint pesticide testing programme carried out by the IOBC/WPRS-Working Group 'Pesticides and beneficial organisms'". Entomophaga. 36: 55–67. doi:10.1007/BF02374636.
97. Preston, CM; Trofymow, JA (1989). "Effects of glyphosate (Roundup) on biological activity of forest soils". Proceedings of the Carnation Creek Workshop: 122–40. ISBN 0-7726-0917-9.
98. Doublet, Jérémy; Mamy, Laure; Barriuso, Enrique (2009). "Delayed degradation in soil of foliar herbicides glyphosate and sulcotrione previously absorbed by plants: Consequences on herbicide fate and risk assessment". Chemosphere. 77 (4): 582–9. doi:10.1016/j.chemosphere.2009.06.044. PMID 19625069.
99. Fernandez, M. R.; Selles, F.; Gehl, D.; Depauw, R. M.; Zentner, R. P. (2005). "Crop Production Factors Associated with Fusarium Head Blight in Spring Wheat in Eastern Saskatchewan". Crop Science. 45 (5): 1908–16. doi:10.2135/cropsci2004.0197.
100. Duke, Stephen O.; Wedge, David E.; Cerdeira, Antonio L.; Matallo, Marcus B. (2007). "Interactions of Synthetic Herbicides with Plant Disease and Microbial Herbicides". In Vurro, Maurizio; Gressel, Jonathan (eds.). Novel Biotechnologies for Biocontrol Agent Enhancement and Management. NATO Security through Science Series. pp. 277–96. doi:10.1007/978-1-4020-5799-1_15. ISBN 978-1-4020-5797-7.
101. ^ Lori (2009-05-07). "U of G Researchers Find Suspected Glyphosate-Resistant Weed". Uoguelph.ca. Retrieved 2010-08-22.
102. "Resisting Roundup". The New York Times. 2010-05-16.
103. ISU Weed Science Online – Are RR Weeds in Your Future I
104. Powles, Stephen B.; Lorraine-Colwill, Debrah F.; Dellow, James J.; Preston, Christopher (1998). "Evolved Resistance to Glyphosate in Rigid Ryegrass (Lolium rigidum) in Australia". Weed Science. 46 (5): 604–7. JSTOR 4045968.
105. Tarter, Steve (2009-04-06). "PJStar.com". PJStar.com. Retrieved 2010-08-22.
106. ^ NEUMAN, WILLIAM (4 May 2010). "U.S. Farmers Cope With Roundup-Resistant Weeds". New York Times. New York. pp. B1. Retrieved 4 May 2010. {{cite news}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
107. "Glyphosate resistance is a reality that should scare some cotton growers into changing the way they do business". Southeastfarmpress.com. Retrieved 2010-08-22.
108. "Map of Glyphosate-Resistant Weeds Globally". The International Survey of Herbicide Resistant Weeds. 2010. Retrieved 12 Jan 2013.
109. Culpepper, A. Stanley; Grey, Timothy L.; Vencill, William K.; Kichler, Jeremy M.; Webster, Theodore M.; Brown, Steve M.; York, Alan C.; Davis, Jerry W.; Hanna, Wayne W. (2006). "Glyphosate-resistant Palmer amaranth (Amaranthus palmeri ) confirmed in Georgia". Weed Science. 54 (4): 620–6. doi:10.1614/WS-06-001R.1. JSTOR 4539441. {{cite journal}}: hair space character in |title= at position 57 (help)
110. ^ Hampton, Natalie. "Cotton versus the monster weed". Retrieved 2009-07-19.
111. ^ Smith, J.T. (March 2009). "Resistance a growing problem" (PDF). The Farmer Stockman. Retrieved 2009-07-19.
112. Taylor, Owen (2009-07-16). "Peanuts: variable insects, variable weather, Roundup resistant Palmer in new state". PeanutFax. AgFax Media. Retrieved 2009-07-19.
113. Vargas, L.; Bianchi, M.A.; Rizzardi, M.A.; Agostinetto, D.; Dal Magro, T. (2007). "Buva (Conyza bonariensis) resistente ao glyphosate na região sul do Brasil". Planta Daninha (in Portuguese). 25 (3): 573–8. doi:10.1590/S0100-83582007000300017. {{cite journal}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
114. Koger, Clifford H.; Shaner, Dale L.; Henry, W. Brien; Nadler-Hassar, Talia; Thomas, Walter E.; Wilcut, John W. (2005). "Assessment of two nondestructive assays for detecting glyphosate resistance in horseweed (Conyza canadensis)". Weed Science. 53 (4): 438–45. doi:10.1614/WS-05-010R. JSTOR 4047050.
115. Ge, Xia; d'Avignon, D André; Ackerman, Joseph JH; Sammons, R Douglas (2010). "Rapid vacuolar sequestration: The horseweed glyphosate resistance mechanism". Pest Management Science. 66 (4): 345–8. doi:10.1002/ps.1911. PMC 3080097. PMID 20063320.
116. Vila-Aiub, Martin M; Vidal, Ribas A; Balbi, Maria C; Gundel, Pedro E; Trucco, Frederico; Ghersa, Claudio M (2008). "Glyphosate-resistant weeds of South American cropping systems: An overview". Pest Management Science. 64 (4): 366–71. doi:10.1002/ps.1488. PMID 18161884.
117. Preston, Christopher; Wakelin, Angela M.; Dolman, Fleur C.; Bostamam, Yazid; Boutsalis, Peter (2009). "A Decade of Glyphosate-Resistant Lolium around the World: Mechanisms, Genes, Fitness, and Agronomic Management". Weed Science. 57 (4): 435–41. doi:10.1614/WS-08-181.1.
118. Vila-Aiub, Martin M.; Balbi, Maria C.; Gundel, Pedro E.; Ghersa, Claudio M.; Powles, Stephen B. (2007). "Evolution of Glyphosate-Resistant Johnsongrass (Sorghum halepense) in Glyphosate-Resistant Soybean". Weed Science. 55 (6): 566–71. doi:10.1614/WS-07-053.1. JSTOR 4539618.
119. http://www.state.gov/www/regions/wha/colombia/fs_000328_plancolombia.html United States Support For Colombia
120. The Mystery of the Coca Plant That Wouldn't Die
121. BOLIVIANA NEGRA, LA COCA QUE NO MUERE
122. New York Times article mentioning advertising agreement
123. Monsanto Fined in France for 'False' Herbicide Ads
124. "Monsanto guilty in 'false ad' row". BBC News. 15 October 2009.
125. ^ Backgrounder: Testing Fraud: IBT and Craven Labs, June 2005, Monsanto background paper on RoundUp
126. Schneider, K. 1983. Faking it: The case against Industrial Bio-Test Laboratories. The Amicus Journal (Spring): 14–26. Reproduced at Planetwaves Faking It and Planetwaves IBT Guilty
127. EPA FY1994 Enforcement and Compliance Assurance Accomplishments Report
128. Trade: Albaugh accuses Chinese of dumping herbicide
129. In the Matter of: GLYPHOSATE FROM CHINA
130. Heck, G. R.; Armstrong, C. L.; Astwood, J. D.; Behr, C. F.; Bookout, J. T.; Brown, S. M.; Cavato, T. A.; Deboer, D. L.; Deng, M. Y. (2005). "Development and Characterization of a CP4 EPSPS-Based, Glyphosate-Tolerant Corn Event". Crop Science. 45: 329–39. doi:10.2135/cropsci2005.0329.
131. Funke, Todd; Han, Huijong; Healy-Fried, Martha L.; Fischer, Markus; Schönbrunn, Ernst (2006). "Molecular basis for the herbicide resistance of Roundup Ready crops". Proceedings of the National Academy of Sciences. 103 (35): 13010–5. Bibcode:2006PNAS..10313010F. doi:10.1073/pnas.0603638103. JSTOR 30050705. PMC 1559744. PMID 16916934.
132. Monsanto Company History – Monsanto Web Site – monsanto.com
133. Acreage NASS National Agricultural Statistics Board annual report, June 30, 2010. Retrieved August 26, 2012.

• Herbicides
• Acetic acids
• Amines
• Phosphonic acids