Glyphosate

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Glyphosate
Glyphosate-2D-skeletal.png
Glyphosate-3D-balls.png
IUPAC name N-(phosphonomethyl)glycine
Other names 2-[(phosphonomethyl)amino]acetic acid
Identifiers
InChI InChI=1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9​)
CAS number [1071-83-6],
38641-94-0 (isopropylammmonium salt)
70393-85-0 (sesquisodium salt)
81591-81-3 (trimethylsulfonium salt)
EC number 213-997-4
RTECS MC1075000
ChemSpider 3376
PubChem 3496
SMILES
Properties[1]
Molecular formula C3H8NO5P
Molar mass 169.07 g mol−1
Appearance white crystalline powder
Density 1.704 (20 °C)
Melting point

184.5 °C

Boiling point

decomp. 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[1][2]
Material safety data sheet (MSDS) ICSC 0160
EU index number 607-315-00-8
GHS pictograms Eye Dam. 1Aquatic Chronic 2
GHS signal word DANGER
GHS hazard statements H318, H411
GHS precautionary statements P273, P280, P305+351+338, P310, P501
Flash point non-flammable
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Glyphosate (N-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide used to kill weeds, especially perennials. It is typically sprayed and absorbed through the leaves, injected into the trunk, or applied to the stump of a tree, or broadcast or used in the cut-stump treatment as a forestry herbicide. Initially patented and sold by Monsanto Company in the 1970s under the tradename Roundup, its U.S. patent expired in 2000. It is now also available in other formulations, e.g. Resolva 24H, which contains glyphosate and diquat.[3] Glyphosate is the most used herbicide in the USA.[4] In the US, 5–8 million pounds (2200–3600 tonnes) are used every year on lawns and yards and 85–90 million pounds (about 40,000 tonnes) are used annually in US agriculture.[4]

The active ingredient is the isopropylamine salt of glyphosate. Glyphosate's mode of action is to inhibit an enzyme involved in the synthesis of the 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). Such crops allow farmers to use glyphosate as a post-emergence herbicide against both broadleaf and cereal weeds. 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 glycine, phospho-, and -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 12g/L at room temperature.

Glyphosate was first discovered to have herbicidal activity in 1970 by John E. Franz, while working for Monsanto.[5] Franz received the National Medal of Technology in 1987,[6] and the Perkin Medal for Applied Chemistry.[7] in 1990 for his discoveries.

Formulas and tradenames

Although the Roundup trademark is registered with the US Patent Office and still extant, the patent has expired. Glyphosate is marketed in the US and worldwide in different solution strengths under many tradenames:[8] Roundup, Buccaneer, Razor Pro (41%), Genesis Extra II (41% w/ Surfactant), Roundup Pro Concentrate (50.2 %), Rodeo (51.2%), Aquaneat (53.8%), and Aquamaster (53.5%)[9]. These products may contain other ingredients, causing them to have different effects. For example, Roundup was found to have different effects to glyphosate alone.[10] Roundup is a water based solution containing glyphosate, a surfactant, and other substances.

Biochemistry

Glyphosate kills plants by interfering with the synthesis of the 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). ESP is subsequently dephosphorylated to chorismate, an essential precursor in plants for the aromatic amino acids: phenylalanine, tyrosine and tryptophan.[11] These amino acids are used as building blocks in peptides, 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 phosphoenol pyruvate, mimicking an intermediate state of the ternary enzyme substrates complex.[12] The shikimate pathway is not present in animals, which instead obtain aromatic amino acids from their diet. Glyphosate has also been shown to inhibit other plant enzymes[13][14] and also has been found to affect animal enzymes.[15]

Use

Roundup used as an alternative to mowing in an apple orchard in Ciardes, Italy

Glyphosate is effective in killing a wide variety of plants, including grasses, broadleaf, and woody plants.[16] It has a relatively small effect on some clover species.[17] By volume, it is one of the most widely used herbicides.[18] It is commonly used for agriculture, horticulture, and silviculture purposes, as well as garden maintenance (including home use).[18]

Glyphosate is supplied in several formulations for different uses:

  • Ammonium salt.
  • Isopropylamine salt.
  • Glyphosate acid - standalone, as ammonium salt or as isopropyl salt.
  • potassium salt

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.[ref. needed] More commonly, rates of 3 litres per hectare are practiced for control of annual weeds between crops.[19]

Genetically modified crops

In 1996, genetically modified soybeans were made commercially available.[20] Current Roundup Ready crops include soy, maize (corn), sorghum, canola, alfalfa, and cotton, with wheat still under development. These cultivars greatly improved conventional farmers' ability to control weeds since glyphosate could be sprayed on fields without hurting the crop. As of 2005, 87% of U.S. soybean fields were planted with glyphosate resistant varieties.[21][22]

While the use of Roundup Ready crops may have increased the usage of herbicides measured in pounds applied per acre.[23], the use of Roundup Ready crops has changed the herbicide use profile away from atrazine, metribuzin, and alachlor. This has the benefit of reducing the dangers of herbicide run off into drinking water.[24]

In 1999, a review of Roundup Ready soybean crops found that, compared to the top conventional varieties, they had a 6.7% lower yield [23]. This so called "yield drag" follows the same pattern observed when other traits are introduced into soybeans by conventional breeding [25] and can not be attributed to the Roundup Ready trait or the GM nature of the crop since Monsanto have recently released Roundup Ready 2 Soybeans which yields 7-11% higher than RR version 1 [26]. There have been no reports of "yield drag" with the other Roundup Ready crops maize, sorghum or canola.

Development

Some micro-organisms have a version of 5-enolpyruvoyl-shikimate-3-phosphate synthetase (EPSPS) that is resistant to glyphosate inhibition. The version used in genetically modified crops was isolated from Agrobacterium strain CP4 (CP4 EPSPS) that was resistant to glyphosate.[27][28] This CP4 EPSPS gene was cloned and transfected into soybeans. The CP4 EPSPS gene was engineered for plant expression by fusing the 5' end of the gene to a chloroplast transit peptide derived from the petunia EPSPS. This transit peptide was used because it had shown previously an ability to deliver bacterial EPSPS to the chloroplasts of other plants. The plasmid used to move the gene into soybeans was PV-GMGTO4. It contained three bacterial genes, two PC4 EPSPS genes, and a gene encoding beta-glucuronidase (GUS) from Escherichia coli as a marker. The DNA was injected into the soybeans using the particle acceleration method. Soybean cultivar A54O3 was used for the transformation. The expression of the GUS gene was used as the initial evidence of transformation. GUS expression was detected by a staining method in which the GUS enzyme converts a substrate into a blue precipitate. Those plants that showed GUS expression were then taken and sprayed with glyphosate and their tolerance was tested over many generations.

Other uses

Glyphosate is one of a number of herbicides used by the United States government to spray Colombian coca fields through Plan Colombia. Its health effects, effects on legal crops, and effectiveness in fighting the war on drugs have been widely disputed.[29] 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 known as Boliviana negra, which have been selectively bred to be both "Roundup ready" and also larger and higher yielding than the original strains of the plant.[30] 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.

Toxicity

Glyphosate is less toxic than a number of other herbicides and pesticides, such as those from the organochlorine family.[31] Roundup has a United States Environmental Protection Agency‎ (EPA) Toxicity Class of III for oral and inhalation exposure,[32] but more recent studies suggest that IV is appropriate for oral, dermal, and inhalation exposure.[33] It has been rated as class I (Severe) for eye irritation, however.[33]

A 2000 review of the available literature concluded that "under present and expected conditions of new use, there is no potential for Roundup herbicide to pose a health risk to humans".[33] A recent study, on the other hand, has shown that Roundup formulations and metabolic products cause the death of human embryonic, placental, and umbilical cells in vitro even at low concentrations. The effects are not proportional to Glyphosate concentrations but dependent on the nature of the adjuvants used in the formulation.[34]

Humans

A review of the literature in 2000 concluded that "under present and expected conditions of new use", and based upon screening tests, there are no known toxic effects for Roundup herbicide to humans.[33] This review considered the likely effects experienced by the two groups most likely to have high exposures, herbicide applicators and children aged 1–6, noting that the normal exposure in those sub-populations does not cause toxic effects.[33] Glyphosate has a United States Environmental Protection Agency‎ Toxicity Class of III in 1993,[32] but more recent studies suggest that IV is appropriate for oral, dermal, and inhalation exposure.[33] It has been rated as class I (Severe) for eye irritation, however.[33] Glyphosate is being evaluated for effects to unborn fetuses and their development. It is currently on the USEPA Endocrine Disrupter Screening list, published in 2007.[35][36]

Outside its intended use, glyphosate can be lethal. For example, with intentional poisonings there is approximately a 10% mortality for those ingesting glyphosate, compared to 70% for those ingesting paraquat.[37]

Laboratory toxicology studies suggest that other ingredients combined with glyphosate may have greater toxicity than glyphosate alone. For example, a study comparing glyphosate and Roundup found that Roundup had a greater effect on aromatase than glyphosate alone.[10]

Statistics from the California Environmental Protection Agency's Pesticide Illness Surveillance Program indicate that glyphosate related incidents are one of the highest reported of all pesticides.[38][39] However, incident count does not take into account the number of people exposed and the severity of symptoms associated with each incident.[39] For example if hospitalization is used as a measure of the severity of pesticide related incidents, then Glyphosate would be considered relatively safe, since over a 13 year period in California none of the 515 pesticide related hospitalizations recorded were attributed to glyphosate.[39]

Greenpeace states that the acute human toxicity of glyphosate is very low, but note that, as mentioned above, other added chemicals (particularly surfactants, e.g. polyoxy-ethyleneamine, POEA) can be more toxic than glyphosate itself.[16] Over-application, or application directly to the soil may impact earth worms.

A review of the toxicological data on Roundup shows that there are at least 58 studies of the effects of Roundup itself on a range of organisms.[40] This review concluded that "for terrestrial uses of Roundup minimal acute and chronic risk was predicted for potentially exposed non-target organisms". It also concluded that there were some risks to aquatic organisms exposed to Roundup in shallow water. More recent research suggests glyphosate induces a variety of functional abnormalities in fetuses and pregnant rats.[41] Also in recent mammalian research, glyphosate has been found to interfere with an enzyme involved testosterone production in mouse cell culture[42] and to interfere with an estrogen biosynthesis enzyme in cultures of Human Placental cells.[43]

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. 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. [44]

Other species

The direct toxicity of pure glyphosate to mammals and birds is low.[45] Template:Verify credibility The acute oral toxicity of Roundup is > 5,000 mg/kg in the rat.[46] It showed no toxic effects when fed to animals for 2 years, and only produced rare cases of reproductive effects when fed in extremely large doses to rodents and dogs. It has not demonstrated any increase in cancer rates in animal studies and is poorly absorbed in the digestive tract. Glyphosate has no significant potential to accumulate in animal tissue.[47][48]

An in vitro study indicates that glyphosate formulations could harm earthworms[49] and beneficial insects.[50] However, the reported effect of glyphosate on earthworms has been criticized.[40] 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.[51] Glyphosate can negatively affect nitrogen-fixing bacteria,[52] and increase the susceptibility of plants to disease.[53] A 2005 study concluded that certain amphibians may be at risk from glyphosate use.[54]

Certain surfactants used in some glyphosate formulations have higher toxicity to fish and invertebrates resulting in some formulations of glyphosate not being registered for use in aquatic applications.[55] Monsanto produces glyphosate products with alternative surfactants that are specifically formulated for aquatic use, for example "Biactive" and "AquaMaster".[56] According to Monsanto, "Conservation groups have chosen glyphosate formulations because of their effectiveness against most weeds as glyphosate has very low toxicity to wildlife".[57] Glyphosate is used with 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. [44]

Glyphosate's effect on soil life may be limited because when glyphosate comes into contact with the soil, it rapidly binds to soil particles and is inactivated.[58][59] Unbound glyphosate is degraded by bacteria. Low activity because of binding to soil particles suggests that glyphosate's effects on soil flora are limited. Low glyphosate concentrations can be found in many creeks and rivers in U.S. and Europe.[ref. needed]

The United States Environmental Protection Agency,[58] the EC Health and Consumer Protection Directorate, and the UN World Health Organization have all concluded that pure glyphosate is not carcinogenic. Opponents of glyphosate claim that Roundup has been found to cause genetic damage, citing Peluso et al.[60] The authors concluded that 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.[61]

Aquatic effects

Fish and aquatic invertebrates are more sensitive to Roundup than terrestrial organisms.[40] Glyphosate is generally less persistent in water than in soil, with 12 to 60 day persistence observed in Canadian pond water, yet persistence of over a year have been observed in the sediments of ponds in Michigan and Oregon.[32]
The EU classifies Roundup as R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.[62]

Roundup is not registered for aquatic uses[63] and studies of its effects on amphibians indicate it is toxic to them.[64] Other glyphosate formulations that are registered for aquatic use have been found to have negligible adverse effects on sensitive amphibians.[65]

Endocrine disruptor debate

In vitro studies have shown glyphosate affects progesterone production in mammalian cells[66] and can increase the mortality of placental cells.[10] Whether these studies classify glyphosate as an endocrine disruptor is debated.

SomeTemplate:Who feel that in vitro studies are insufficient, and are waiting to see if animal studies show a change in endocrine activity, since a change in a single cell line may or may not impact an entire organism. Additionally, current in vitro studies expose cell lines to concentrations orders of magnitude greater than would be found in expected exposures, and through pathways that would not be typically experienced in real organisms.

OthersTemplate:Who feel that in vitro studies, particularly ones identifying not only an effect, but a chemical pathway, are sufficient evidence to classify glyphosate as an endocrine disruptor, on the basis that even small changes in endocrine activity can have lasting effects on an entire organism that may be difficult to detect through whole organism studies alone. Further research on the endocrine effects of glyphospate is ongoing, including through the EPA endocrine screening program on 73 chemicals, published in 2007.

Environmental degradation

When glyphosate comes into contact with the soil it can be rapidly bound to soil particles and be inactivated.[32] Unbound glyphosate can be degraded by bacteria.[67] However, glyphosphate has been shown to increase the infection rate of wheat by fusarium head blight in fields that have been treated with glyphosphate. [68]

In soils, half lives vary from as little as 3 days at a site in Texas, 141 days at a site in Iowa, to between 1–3 years in Swedish forest soils.[69] It appears that higher latitude sites have the longest soil persistences such as in Canada and Scandinavia.

Resistance in weeds and microorganisms

The first documented cases of weed resistance to glyphosate were found in Australia, involving rigid ryegrass near Orange, New South Wales.[70] Some farmers in the United States have expressed concern that weeds are now developing with glyphosate resistance, with 13 states now reporting resistance, and this poses a problem to many farmers, including cotton farmers, that are now heavily dependent on glyphosate to control weeds.[71][72] Farmers associations are now reporting 103 biotypes of weeds within 63 weed species with herbicide resistance[71][72]. This problem is likely to be exacerbated by the use of roundup-ready crops [73].

Legal cases

False advertising

In 1996 Monsanto was accused of false and misleading advertising of glyphosate products, prompting a law suit by the New York State attorney general.[74]
On Fri Jan 20, 2007, Monsanto was convicted of false advertising of Roundup for presenting Roundup as biodegradable and claiming that 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 France planned to appeal the verdict at the time. [75]

Scientific fraud

On two occasions the United States Environmental Protection Agency has caught scientists deliberately falsifying test results at research laboratories hired by Monsanto to study glyphosate.[76][77][78] In the first incident involving Industrial Biotest Laboratories, an EPA reviewer stated after finding "routine falsification of data" that it was "hard to believe the scientific integrity of the studies when they said they took specimens of the uterus from male rabbits".[79][80][81] In the second incident of falsifying test results in 1991, the owner of the lab (Craven Labs), and three employees were indicted on 20 felony counts, the owner was sentenced to 5 years in prison and fined 50,000 dollars, the lab was fined 15.5 million dollars and ordered to pay 3.7 million in restitution.[82][83] Craven laboratories performed studies for 262 pesticide companies including Monsanto.

Monsanto has stated that the studies have been repeated and that Roundup's EPA certification does not now use any studies from Craven Labs or IBT. Monsanto also claims that the Craven Labs investigation was started by the EPA after a pesticide industry task force discovered irregularities.[84]

References

  1. ↑ 1.0 1.1 Glyphosate; Environmental Health Criteria monograph No. 159; World Health Organization: Geneva, 1994. ISBN 92-4-157159-4, <http://www.inchem.org/documents/ehc/ehc/ehc159.htm>.
  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. OJEU L353, 31.12.2008, pp 1–1355 at pp 570, 1100..
  3. ↑ <http://www.resolva-weeds.com/index.php> (accessed 4 September 2009), Resolva Weeds; Westland Garden Health.
  4. ↑ 4.0 4.1 Pesticides Industry Sales and Usage: 2000 and 2001 Market Estimates; U.S. Environmental Protection Agency, May 2004; pp 14–15, <http://www.epa.gov/oppbead1/pestsales/01pestsales/market_estimates2001.pdf>.
  5. ↑ Alibhai, Murtaza F.; Stallings, William C. Closing down on glyphosate inhibition—with a new structure for drug discovery. Proc. Natl. Acad. Sci. USA 2001, 98 (6), 2944. PMID 11248008. DOI: 10.1073/pnas.061025898.
  6. ↑ National Medal of Technology Recipients 1987; U.S. Patent and Trademark Office, <http://www.uspto.gov/nmti/recipients_87.html>. (accessed 5 September 2009).
  7. ↑ Stong, Colby People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry. The Scientist 1990, 4 (10), 28, <http://www.the-scientist.com/article/display/10101/>.
  8. ↑ California Product/Label Database; California Department of Pesticide Regulation, <http://www.cdpr.ca.gov/docs/label/labelque.htm#regprods>. (accessed 7 September 2009). Search terms: 2997 Glyphosate (19 entries); 5810 Glyphosate, diammonium salt (9 entries); 5972 Glyphosate, dimethylamine salt (4 entries); 1855 Glyphosate, isopropylamine salt (468 entries); 2301 Glyphosate, monoammonium salt (16 entries); 5820 Glyphosate, potassium salt (12 entries); 2275 Glyphosate, sesquisodium salt (0 entries); 2327 Glyphosate-trimesium (2 entries).
  9. ↑ Glyphosate Roadside Vegetation Management Herbicide Fact Sheet; Washington State Department of Transportation, <http://www.wsdot.wa.gov/maintenance/pdf/glyphosate.pdf>. (accessed 7 September 2009).
  10. ↑ 10.0 10.1 10.2 Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE (June 2005). "Differential effects of glyphosate and roundup on human placental cells and aromatase" (Free full text). Environ. Health Perspect. 113 (6): 716–20. PMID 15929894. 
  11. ↑ Aromatic amino acid biosynthesis. The shikimate pathway – synthesis of chorismate; Department of Horticulture and Landscape Architecture, Purdue University, <http://www.hort.purdue.edu/rhodcv/hort640c/aromat/ar00007.htm>. (accessed 7 September 2009).
  12. ↑ Schönbrunn, Ernst; Eschenburg, Susanne; Shuttleworth, Wendy A.; Schloss, John V.; Amrhein, Nikolaus; Evans, Jeremy N. S.; Kabsch, Wolfgang Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail. Proc. Natl. Acad. Sci. USA 2001, 98 (4), 1376–80, <http://www.pnas.org/cgi/content/full/98/4/1376?ijkey=1b1ce735beee08811872889841023d179742ef2c>.
  13. ↑ Su, L. Y.; de la Cruz, A.; Moore, P. H.; Maretzki, A. The relationship of glyphosate treatment to sugar metabolism in sugarcane: New physiological insights. J. Plant Physiol. 1992, 140, 168–73.
  14. ↑ Lamb, D. C.; Kelly, D. E.; Hanley, S. Z.; Mehmood, Z.; Kelly, S. L. Glyphosate is an Inhibitor of Plant Cytochrome P450: Functional Expression of Thlaspi arvensae Cytochrome P45071B1/Reductase Fusion Protein in Escherichia coli. Biochem. Biophys. Res. Comm. 1998, 244 (1), 110–14. DOI: 10.1006/bbrc.1997.7988.
  15. ↑ Hietanen, Eino; Linnainmaa, Kaija; Vainio, Harri Effects of phenoxy herbicides and glyphosate on the hepatic and intestinal biotransformation activities in the rat. Acta Pharmacol. Toxicol. 1983, 53 (2), 103–12. DOI: 10.1111/j.1600-0773.1983.tb01876.x.
  16. ↑ 16.0 16.1 Greenpeace. (1997). Weed Killing Crops: Glyphosate and Your Food (archived)
  17. ↑ Integrated Pest Management Template:Deadlink
  18. ↑ 18.0 18.1 U.S. Environmental Protection Agency. (2006). Technical Factsheet on: GLYPHOSATE [1] Template:Deadlink
  19. ↑ e-phy: Le catalogue des produits phytopharmaceutiques et de leurs usages des matières fertilisantes et des supports de culture homologués en France; French Ministry of Agriculture and Fisheries, <http://e-phy.agriculture.gouv.fr/>. (accessed 7 September 2009).
  20. ↑ Company History; Monsanto, <http://www.monsanto.com/who_we_are/history.asp>. (accessed 7 September 2009).
  21. ↑ Petition for Non-regulated Status for Soybean Line MON 89788 (APHIS 06-178-01p) – Finding of No Significant Impact; Animal and Plant Health Inspection Service, U.S. Department of Agriculture; p 13, <http://www.aphis.usda.gov/brs/aphisdocs/06_17801p_ea.pdf>.
  22. ↑ Acreage; Johanns, M.; Wiyatt, S. D., Eds.; National Agriculture Statistics Service, U.S. Department of Agriculture, 2005.
  23. ↑ 23.0 23.1 Benbrook, Charles Evidence of the Magnitude and Consequences of the Roundup Ready Soybean Yield Drag from University-Based Varietal Trials in 1998; Ag BioTech InfoNet Technical Paper Number 1, July 1999, <http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.41.823&rep=rep1&type=pdf>.
  24. ↑ Shipitalo, Martin J.; Malone, Robert W.; Owens, Lloyd B. Impact of glyphosate-tolerant soybean and glufosinate-tolerant corn production on herbicide losses in surface runoff. J. Environ. Qual. 2008, 37 (2), 401–8. PMID 18268303. DOI: 10.2134/jeq2006.0540.
  25. ↑ Caviness, C.E., and H.J. Walters. 1971. Effect of phytophthora rot on yield and chemical composition of soybean seed. Crop Science 11:83-84
  26. ↑ Roundup Ready 2 Yield®; Monsanto, <http://www.monsanto.com/rr2y/>. (accessed 7 September 2009).
  27. ↑ Heck, G. R.; et al. Development and Characterization of a CP4 EPSPS-Based, Glyphosate-Tolerant Corn Event. Crop Sci. 2005, 45 (1), 329–39, <http://crop.scijournals.org/cgi/content/full/45/1/329>.
  28. ↑ Funke, Todd; Han, Huijong; Healy-Fried, Martha L.; Fischer, Markus; Schönbrunn, Ernst Molecular basis for the herbicide resistance of Roundup Ready crops. Proc. Natl. Acad. Sci. USA 2006, 103, 13010–15. PMID 16916934. doi:10.1073/pnas.0603638103, <http://www.pnas.org/cgi/content/full/103/35/13010>.
  29. ↑ Isacson, Adam; Myers, John Plan Colombia’s Drug Eradication Program Misses the Mark; Center for International Policy, July 2005, <http://americas.irc-online.org/am/166>. (accessed 7 September 2009).
  30. ↑ McDermott, Jeremy New Super Strain of Coca Plant Stuns Anti-Drug Officials. The Scotsman 27 August 2004, <http://news.scotsman.com/latestnews/New-super-strain-of-coca.2559109.jp>.
  31. ↑ Raspberry IPM Manual -Pesticide Selection
  32. ↑ 32.0 32.1 32.2 32.3 U.S. EPA ReRegistration Decision Fact Sheet for Glyphosate (EPA-738-F-93-011) 1993. [2] Cite error: Invalid <ref> tag; name "epa_reds" defined multiple times with different content
  33. ↑ 33.0 33.1 33.2 33.3 33.4 33.5 33.6 Williams GM, Kroes R, Munro IC. (2000) Safety evaluation and risk assessment of the herbicide Roundup and its active ingredient, glyphosate, for humans. Regulatory Toxicology and Pharmacology, 31 (2): 117-165. PMID 10854122.
  34. ↑ Benachour, Nora; Gilles-Eric Séralini (December 23, 2008). "Glyphosate Formulations Induce Apoptosis and Necrosis in Human Umbilical, Embryonic, and Placental Cells". Chemical Research in Toxicology 22: 97. doi:10.1021/tx800218n. 
  35. ↑ USEPA Federal Register http://www.epa.gov/endo/pubs/draft_list_frn_061807.pdf
  36. ↑ Accustandard, Chemical Reference Standards, http://www.accustandard.com/asi/np_endocrine_disruptors.php3
  37. ↑ Nagami H, Nishigaki Y, Matsushima S, et al. (2005). "Hospital-based survey of pesticide poisoning in Japan, 1998--2002". Int J Occup Environ Health 11 (2): 180–4. PMID 15875894. 
  38. ↑ GGoldstein DA, Acquavella JF, Mannion RM, Farmer DR (2002). "An analysis of glyphosate data from the California Environmental Protection Agency Pesticide Illness Surveillance Program". J. Toxicol. Clin. Toxicol. 40 (7): 885–92. doi:10.1081/CLT-120016960. PMID 12507058. 
  39. ↑ 39.0 39.1 39.2 California EPA 1996, California Pesticide Illness Serveillance Program Report HS-1733 [3]
  40. ↑ 40.0 40.1 40.2 JP Giesy, KR Solomon, S Dobson (2000). "Ecotoxicological Risk Assessment for Roundup Herbicide". Reviews of Environmental Contamination and Toxicology 167: 35-120
  41. ↑ Effect of the herbicide glyphosate on enzymatic ac...[Environ Res. 2001] - PubMed Result
  42. ↑ Walsh et al. Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (StAR) protein expression. Environ Health Perspect. 2000 108: 769–776.[4]
  43. ↑ Richard et al., Differential Effects of Glyphosate and Roundup on Human Placental Cells and Aromatase, Environmental Health Perspectives Vol. 113, No.6, 716-720[5]
  44. ↑ 44.0 44.1 Review article at of glyphosate poisoning at Pubmed by Bradberry SM, Proudfoot AT, Vale JA. of the National Poisons Information Service (Birmingham Centre) and West Midlands Poisons Unit, City Hospital, Birmingham, UK. http://www.ncbi.nlm.nih.gov/pubmed/15862083
  45. ↑ pest control from ipmofalaska.com.
  46. ↑ Roundup PRO Herbicide MSDS
  47. ↑ Extoxnet Pip - Glyphosate
  48. ↑ http://npic.orst.edu/factsheets/glyphogen.pdf
  49. ↑ JA Springett and RAJ Gray (1992). "Effect of repeated low doses of biocides on the earthworm Aporrectodea caliginosa in laboratory culture". Soil Biol and Biochem 24 (12): 1739–1744. doi:10.1016/0038-0717(92)90180-6. 
  50. ↑ Hassan, S. A. (1991). "Results of the fifth joint pesticide testing programme carried out by the IOBC/WPRS-Working Group “Pesticides and beneficial organisms”". Entomophaga 36: 55. doi:10.1007/BF02374636. 
  51. ↑ CM Preston and J.A. Trofymow. 1989. Effects of glyphosate (Roundup) on biological activity of forest soils. In: Proceedings of Carnation Creek Workshop, ed. P. Reynolds. Namaimo 7-10 December 1987. Forest Canada/British Columbia ministry of forests, 122-140.
  52. ↑ Santos A, Flores M. (1995). "Effects of glyphosate on nitrogen fixation of free-living heterotrophic bacteria". Letters in Applied Microbiology 20 (6): 349–352. doi:10.1111/j.1472-765X.1995.tb01318.x. Retrieved on 2009-04-15. 
  53. ↑ Duke SO et al. (2007). "Herbicide effects on plant disease". Outlooks Pest Manag 18: 36–40. doi:10.1564/18feb13. Retrieved on 2009-04-15. 
  54. ↑ Bette Hileman. (2005) Common herbicide kills tadpoles. Chemical & Engineering News. Washington 83(15):11.
  55. ↑ Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities", Monsanto Corporation Backgrounder [6]
  56. ↑ Aquatic Use of Glyphosate Herbicides in Australia, Monsanto Corporation Backgrounder[7]
  57. ↑ [8]
  58. ↑ 58.0 58.1 US EPA Reregistration Eligibility Decision - Glyphosate
  59. ↑ M.M. de Andréa, et al. (2003 2003). "Influence of repeated applications of glyphosate on its persistence and soil bioactivity". Pesq. Agropec. Bras. 38 (11): 1329–1335. 
  60. ↑ Peluso M, Munnia A, Bolognesi C, Parodi S. Environ Mol Mutagen. 1998 31:55-9 PMID 9464316
  61. ↑ Daruich J, Zirulnik F, Gimenez MS (March 2001). "Effect of the herbicide glyphosate on enzymatic activity in pregnant rats and their fetuses". Environ. Res. 85 (3): 226–31. doi:10.1006/enrs.2000.4229. PMID 11237511. 
  62. ↑ http://lscgw1.monsanto.com/esh/msdslib.nsf/2B20DAEB04E8631C0625689700650B45/$file/Roundup%20Ultra%203000-5059en-gb.pdf Roundup Material Safety Data sheet page 7, heading 16
  63. ↑ Monsanto Backgrounder 2005 Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities" [9]
  64. ↑ Rick A. Relyea 2005 The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities Ecological Applications 15:618–627
  65. ↑ Wojtaszek et al. Effects of vision herbicide on mortality, avoidance response, and growth of amphibian larvae in two forest wetlands Environmental Toxicology and Chemistry 23:832–842 2004
  66. ↑ Walsh LP, McCormick C, Martin C, Stocco DM (August 2000). "Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (StAR) protein expression". Environ. Health Perspect. 108 (8): 769–76. doi:10.2307/3434731. PMID 10964798. 
  67. ↑ Balthazor, Terry M and Laurence Hallas (1986) Glyphosate-degrading microorganisms in industrial waste treatment biosystems. Appl. Environ. Microbiol. 51:432-34.[10]
  68. ↑ [11] "Crop Production Factors Associated with Fusarium Head Blight in Spring Wheat in Eastern Saskatchewan", published online 26 August 2005 by M. R. Fernandeza, F. Sellesa, D. Gehlb, R. M. DePauwa and R. P. Zentner.
  69. ↑ Glyphosate Factsheet (part 1 of 2) Caroline Cox / Journal of Pesticide Reform v.108, n.3 Fall98 rev.Oct00
  70. ↑ ISU Weed Science Online - Are RR Weeds in Your Future II
  71. ↑ 71.0 71.1 Glyphosate resistance is a reality that should scare some cotton growers into changing the way they do business
  72. ↑ 72.0 72.1 More glyphosate resistant weeds
  73. ↑ http://www.chem.purdue.edu/courses/chm333/Roundup%20Article.pdf
  74. ↑ Attorney General of the State of New York. Consumer Frauds and Protection Bureau. Environmental Protection Bureau. 1996. In the matter of Monsanto Company, respondent. Assurance of discontinuance pursuant to executive law § 63(15). New York, NY, Nov
  75. ↑ Monsanto Fined in France for 'False' Herbicide Ads
  76. ↑ (US EPA Communications and Public Affairs 1991 Note to correspondents Washington DC Mar 1)
  77. ↑ (US EPA Communications and Public Affairs 1991 Press Advisory. EPA lists crops associated with pesticides for which residue and environmental fate studies were allegedly manipulated. Washington DC Mar 29)
  78. ↑ (U.S. Congress. House of Representatives. Com. on Gov. Oper. 1984. Problems palgue the EPA pesticide registration activities. House Report 98-1147)
  79. ↑ (U.S. EPA 1978 Data validation. Memo from K LOcke, Toxicology Branch, to R Taylor, Registration Branch. Washington DC Aug 9)
  80. ↑ (U.S. EPA Office of pesticides and Toxic Substances 1983, Summary of the IBT review program. Washington D.C. July)
  81. ↑ Schneider, K. 1983. Faking it: The case against Industrial Bio-Test Laboratories. The Amicus Journal (Spring):14-26. Reproduced at Planetwaves
  82. ↑ (US Dept. of Justice. United States Attorney. Western District of Texas 1992. Texas laboratory, its president, 3 employees indicted on 20 felony counts in connection with pesticide testing. Austin TX Sept 29)
  83. ↑ (US EPA Communications, Education, And Public Affairs 1994 Press Advisory. Craven Laboratories, owner, and 14 employees sentenced for falsifying pesticide tests. Washington DC Mar 4)
  84. ↑ Backgrounder: Testing Fraud: IBT and Craven Labs, June 2005, Monsanto background paper on RoundUp[12]

Further reading

  • Baccara, Mariagiovanna, et al. Monsanto's Roundup, NYU Stern School of Business: August 2001, Revised July 14, 2003.
  • Pease W S et al. (1993) Preventing pesticide-related illness in California agriculture: Strategies and priorities. Environmental Health Policy Program Report. Berkeley, CA: University of California. School of Public Health. California Policy Seminar.
  • Wang Y, Jaw C and Chen Y (1994) Accumulation of 2,4-D and glyphosate in fish and water hyacinth. Water Air Soil Pollute. 74:397-403

External links

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Template:Herbicides

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