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It has been suggested that Roundup and Talk:Glyphosate#Merge be merged into this article. (Discuss) Proposed since June 2008.

Glyphosate

Names
IUPAC name acetic acid
Identifiers
CAS Number	1071-83-6
3D model (JSmol)	Interactive image
ECHA InfoCard	100.012.726
PubChem CID	3496
CompTox Dashboard (EPA)	DTXSID1024122
SMILES C(C(=O)O)NCP(=O)(O)O
Properties
Chemical formula	C3H8NO5P
Molar mass	169.073 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Glyphosate (N-(phosphonomethyl) glycine) is a broad-spectrum systemic herbicide, absorbed through the leaves, injected into the trunk, or applied to the stump of a tree, used to kill weeds, especially perennials and broadcast or used in the cut-stump treatment as a forestry herbicide. Initially patented and sold by Monsanto 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. Glyphosate is the most used herbicide in the USA. In the US, 5-8 million pounds are used every year on lawns and yards and 85-90 million pounds are used annually in US agriculture.

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 (e.g. 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. Franz received the National Medal of Technology in 1987 , and the Perkin Medal for Applied Chemistry. in 1990 for his discoveries.

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. These amino acids are used as building blocks in peptides, and to produce secondary metabolites such as folates, ubiquinones and naphthoquinone. 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 and also has been found to affect animal enzymes.

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, and silviculture purposes, as well as garden maintenance (including home use).

Glyphosate is supplied in several formulations for different uses:

• Ammonium salt.
• Isopropyl amine 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 680g active ingredient per litre. The most common formulation in agriculture is 360g, either alone or with added cationic surfactants.

For 360g 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.

Genetically modified crops

In 1996, genetically modified soybeans were made commercially available. 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.

As of 2005, 87% of U.S. soybean fields were planted to glyphosate resistant varieties.

While the use of roundup ready crops may have increased the usage of herbiices measured in pounds applied per acre., 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.

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

The use of such 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.

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. 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.

Toxicity

Glyphosate is less toxic than a number of other herbicides and pesticides, such as those from the organochlorine family.

Humans

A review of the literature in 2000 concluded that "under present and expected conditions of new use, there is no potential for Roundup herbicide to pose a health risk to humans". 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 the exposure in those subpopulations was not a health concern. Glyphosate has a United States Environmental Protection Agency‎ Toxicity Class of III in 1993, but more recent studies suggest that IV is appropriate for oral, dermal, and inhalation exposure. It has been rated as class I (Severe) for eye irritation, however.

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.

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.

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. However, incident count does not take into account the number of people exposed and the severity of symptoms associated with each incident. 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.

Greenpeace states that "the acute 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.

Other species

The direct toxicity of pure glyphosate to mammals and birds is low. In vitro studies indicate glyphosate formulations could harm earthworms and beneficial insects. However, the 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. Glyphosate can negatively effect nitrogen-fixing bacteria, and increase the susceptibility of plants to disease. A 2005 study concluded that certain amphibians may be at risk from glyphosate use.

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. Monsanto produces glyphosate products with alternative surfactants that are specifically formulated for aquatic use, for example "Biactive" and "AquaMaster". According to Monsanto, "Conservation groups have chosen glyphosate formulations because of their effectiveness against most weeds as glyphosate has very low toxicity to wildlife".

When glyphosate comes into contact with the soil, it rapidly binds to soil particles and is inactivated. 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.

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

Endocrine disruptor debate

In vitro studies have shown glyphosate affects progesterone production in mammalian cells and can increase the mortality of placental cells. Whether these studies classify glyphosate as an endocrine disruptor is a matter of debate.

Some 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 not occur in an entire organism. Additionally, current in vitro studies expose cell lines to concentrations orders of magnitude greater than would be found in real conditions, and through pathways that would not be experienced in real organism.

Others 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 topic has been planned, and should shed more light on the debate.

Environmental degradation

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. Glyphosphate has been shown to increase the infection rate of wheat by fusarium head blight in fields that have been treated with glyphosphate.

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. 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. 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. Farmers associations are now reporting 103 biotypes of weeds within 63 weed species with herbicide resistance. This problem is likely to be exacerbated by the use of roundup-ready crops .

Tradenames

Glyphosate is marketed in the US and worldwide in different solution strengths under many tradenames: 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%).

References

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2. ^ US EPA 2000–2001 Pesticide Market Estimates Agriculture, Home and Garden
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4. Technology Administration: National Medal of Technology RECIPIENTS
5. People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry, The Scientist 1990, 4(10):28 John Franz's Perkin Medal
6. The shikimate pathway - synthesis of chorismate
7. S. cerevisiae Pathway: chorismate biosynthesis
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18. USDA/APHIS Environmental Assessment - In response to Monsanto Petition 06-178-01p seeking a Determination of Non-regulated Status for Roundup RReady2Yield Soybean MON 89788, OECD Unique Identifier MON-89788-1, U.S. Department of Agriculture Animal and Plant Health Inspection Service Biotechnology Regulatory Services page 13
19. National Agriculture Statistics Service (2005) in Acreage eds. Johanns, M. & Wiyatt, S. D. 6 30, (U.S. Dept. of Agriculture, Washington, DC).
20. ^ Charles Benbrook. 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
21. Impact of glyphosate-tolerant soybean and glufosinate-tolerant corn production on herbicide losses in surface runoff. Shipitalo MJ, Malone RW, Owens LB. J Environ Qual. 2008 37(2):401-8 PMID 18268303
22. 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
23. Roundup Ready 2 Yield- Monsanto Web site http://www.monsanto.com/rr2y/
24. Shipitalo MJ, Malone RW, Owens LB (2008). "Impact of glyphosate-tolerant soybean and glufosinate-tolerant corn production on herbicide losses in surface runoff". J. Environ. Qual. 37 (2): 401–8. doi:10.2134/jeq2006.0540. PMID 18268303.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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26. T. Funke; et al. (2006). "Molecular basis for the herbicide resistance of Roundup Ready crops" (Free full text). PNAS. 103: 13010–13015. doi:10.1073/pnas.0603638103. PMID 16916934. {{cite journal}}: Explicit use of et al. in: |author= (help)
27. IRC Americas Program Commentary (2005): Plan Colombia’s Drug Eradication Program Misses the Mark
28. Raspberry IPM Manual -Pesticide Selection
29. ^ GM Williams, R Kroes, JC Munro (2000). "Safety evaluation and risk assessment of the herbicide Roundup and its active ingredient, glyphosate, for humans". Regulatory Toxicology and Pharmacology. 31-N2: 117–165. PMID 10854122.{{cite journal}}: CS1 maint: multiple names: authors list (link)
30. ^ 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).
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32. ^ Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE (2005). "Differential effects of glyphosate and roundup on human placental cells and aromatase" (Free full text). Environ. Health Perspect. 113 (6): 716–20. PMC 1257596. PMID 15929894. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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39. 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.
40. "Effects of glyphosate on nitrogen fixation of free-living heterotrophic bacteria". Letters in Applied Microbiology. 20 (6): 349–352. 1995. Retrieved 2009-04-15. {{cite journal}}: Unknown parameter |authors= ignored (help)
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42. Bette Hileman. (2005) Common herbicide kills tadpoles. Chemical & Engineering News. Washington 83(15):11.
43. Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities", Monsanto Corporation Backgrounder
44. Aquatic Use of Glyphosate Herbicides in Australia, Monsanto Corporation Backgrounder
46. US EPA Reregistration Eligibility Decision - Glyphosate
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50. Balthazor, Terry M and Laurence Hallas (1986) Glyphosate-degrading microorganisms in industrial waste treatment biosystems. Appl. Environ. Microbiol. 51:432-34.
51. "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.
52. Glyphosate Factsheet (part 1 of 2) Caroline Cox / Journal of Pesticide Reform v.108, n.3 Fall98 rev.Oct00
53. ISU Weed Science Online - Are RR Weeds in Your Future II
54. ^ Glyphosate resistance is a reality that should scare some cotton growers into changing the way they do business
55. ^ More glyphosate resistant weeds
56. http://www.chem.purdue.edu/courses/chm333/Roundup%20Article.pdf
57. California Product/Label Database
58. Glyphosate Roadside Vegetation Management Herbicide Fact Sheet

• EU (2002). Review report for the active substance glyphosate. Retrieved October 28, 2005.
• KR Solomon, DG Thompson (2003). "Ecological risk assessment for aquatic organisms from over-water uses of glyphosate". Journal of Toxicology and Environmental Health. 6: 289–324. doi:10.1080/10937400306468.
• Environmental Health Criteria 159: Glyphosate. World Health Organization, (1994).
• History of Glyphosate. Monsanto.

External links

• Glyphosate Technical Fact Sheet - National Pesticide Information Center
• Glyphosate General Fact Sheet - National Pesticide Information Center
• Glyphosate Pesticide Information Profile - Extension Toxicology Network
• EPA Reregistration Eligibility Decision Fact Sheet
• Monsanto Website - Background Information about Glyphosate and Roundup
• US weighs costs of Plan Colombia
• Effect of Glyphosate on human placental cells in culture
• Website of the SynBioC research group, working on different types of aminophosphonates
• Glyphosate Stewardship

• Articles to be merged from June 2008
• Herbicides
• Carboxylic acids
• Amines
• Phosphonates