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Glyphosate
IUPAC name	sodium 2-[(hydroxy-oxido- phosphoryl)methylamino]acetic acid
Identifiers
CAS number	[1071-83-6]
PubChem	61933
SMILES	C(C(=O)O)NCP(=O)(O)[O-].[Na+]
InChI	InChI=1/C3H8NO5P.Na/c5-3(6)1-4-2-10(7,8)9; /h4H,1-2H2,(H,5,6)(H2,7,8,9); /q;+1/p-1/fC3H7NO5P.Na/h5,7H; /q-1;m
Properties
Molecular formula	C3H8NO5P
Molar mass	169.05 g mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Glyphosate (N-(phosphonomethyl) glycine is a non-selective systemic herbicide, absorbed through the leaves, used to kill weeds, especially perennials. Some crops have been genetically engineered to be resistant to it. Glyphosate was first sold by Monsanto under the tradename Roundup, but is no longer under patent. Image File history File links Please see the file description page for further information. ... Roundup is the brand name of a systemic, broad-spectrum herbicide produced by the U.S. life sciences giant Monsanto. ... Image File history File links Broom_icon. ... Image File history File links Size of this preview: 800 × 340 pixel Image in higher resolution (1100 × 468 pixel, file size: 24 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Roundup Glyphosate Talk... Image File history File links Size of this preview: 800 × 413 pixel Image in higher resolution (1100 × 568 pixel, file size: 154 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Roundup Glyphosate Talk... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Systemic Relating to, or affecting a particular body system; especially the nervous system. ... This article or section does not cite its references or sources. ... This article does not cite its references or sources. ... Red Valerian, a perennial plant. ... An iconic image of genetic engineering; this autoluminograph from 1986 of a glowing transgenic tobacco plant bearing the luciferase gene, illustrating the possibilities of genetic engineering. ... The Monsanto Company (NYSE: MON) is a multinational agricultural biotechnology corporation. ... Roundup is the brand name of a systemic, broad-spectrum herbicide produced by the U.S. life sciences giant Monsanto. ... A patent is a set of exclusive rights granted by a state to a patentee (the inventor or assignee) for a fixed period of time in exchange for the regulated, public disclosure of certain details of a device, method, process or composition of matter (substance) (known as an invention) which...

Chemistry

Glyphosate is an aminophosphonic analogue of the natural amino acid glycine and the name is a contraction of glycine, phospho-, and -ate. Glyphosate was first discovered to have herbicidal activity in 1970 by John Franz, while working for Monsanto.^[1] In 1987 Franz received the National Medal of Technology for his discoveries,^[2] and in 1990 he received the Perkin Medal for Applied Chemistry.^[3] For the plant, see Glycine (plant). ... For the plant, see Glycine (plant). ... General Name, Symbol, Number phosphorus, P, 15 Chemical series Nonmetals Group, Period, Block 15 (VA), 3 , p Density, Hardness 1823 kg/m3, __ Appearance colorless/red/silvery white Atomic properties Atomic weight 30. ... The National Medal of Technology is an honor granted by the President of the United States to inventors and innovators that have made significant contributions to the development of new and important technology. ... The Perkin Medal is an award given annually by the American section of the Society of Chemical Industry to a scientist residing in America for an innovation in applied chemistry resulting in outstanding commercial development. ...

Biochemistry

Glyphosate kills plants 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 [16], [17]. 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 obtain aromatic amino acids from their diet. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... In chemistry and biology, catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance, called a catalyst, that is itself not consumed by the overall reaction. ... Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. ... Name Phosphoenolpyruvate; Phosphoenolpyruvic acid; PEP Formula C3H5O6P Mass 167. ... The process of removing phosphate groups from an organic compound (as ATP) by hydrolysis ... Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. ... phenylalanine tryptophan tyrosine thyroxine Aromatic amino acids are amino acids which include an aromatic ring. ... Phenylalanine is one of the standard amino acids. ... Phe redirects here. ... Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in cheese[1][2]), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins. ... Tryptophan is an amino acid and essential in human nutrition. ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... Folic acid (the anion form is called folate) is a B-complex vitamin (once called vitamin M) that is important in preventing neural tube defects (NTDs) in the developing human fetus. ... Coenzyme Q (CoQ), also known as ubiquinone or ubiquinol, is a biologically active quinone with an isoprenoid side chain, related in structure to vitamin K and vitamin E. The oxidized structure of CoQ, or Q, is given here: The various kinds of Coenzyme Q can be distinguished by the number... Vitamin K1 (phylloquinone). ... Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. ...

Toxicity

Glyphosate is less toxic than a number of other herbicides and pesticides, such as those from the organochlorine family [18]. An organochlorine compound is an organic compound of chlorine. ...

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".^[4] 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.^[4] Glyphosate has an EPA Toxicity Class of III in 1993,^[5] but more recent studies suggest that IV is appropriate for oral, dermal, and inhalation exposure.^[4] It has been rated as class I (Severe) for eye irritation, however.^[4] EPA redirects here. ... Toxicity Class refers to a classification system for pesticides created by a national or international government-related or -sponsored organization. ...

Outside its intended use, glyphosate can be lethal. For example, with intentional poisonings (e.g. suicide), there is approximately a 10% mortality for those ingesting glyphosate, compared to 70% for those ingesting paraquat.^[6] It has been suggested that Suicide method be merged into this article or section. ... // Paraquat is the trade name for N,N-Dimethyl-4,4-bipyridinium dichloride, a viologen. ...

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.^[7] Roundup is the brand name of a systemic, broad-spectrum herbicide produced by the U.S. life sciences giant Monsanto. ... Aromatase belongs to the group of cytochrome P450 enzymes (EC 1. ...

Statistics from the Californian Environmental Protection Agencies Pesticide Illness Surveillance Program program indicate that glyphosate related incidents are one of the highest reported of all pesticides.^[8] However, incident count does not take into account the number of people exposed and the severity of symptoms associated with each incident.^[9] 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.^[9] Official language(s) English Capital Sacramento Largest city Los Angeles Area  Ranked 3rd  - Total 158,302 sq mi (410,000 km²)  - Width 250 miles (400 km)  - Length 770 miles (1,240 km)  - % water 4. ...

Greenpeace states that "the acute toxicity of glyphosate is very low", but note that, as mentioned above, other chemicals (particularly surfactants, e.g., POEA) can be more toxic than glyphosate itself.^[10] Surfactants, also known as wetting agents, lower the surface tension of a liquid, allowing easier spreading. ...

Other species

The direct toxicity of pure glyphosate to mammals and birds is low [19]. In vitro studies indicate Glyphosate formulations could negatively impact earthworms^[11] and beneficial insects.^[12] However these 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 kg active ingredient per ha.^[13] Orders Subclass Monotremata Monotremata Subclass Marsupialia Didelphimorphia Paucituberculata Microbiotheria Dasyuromorphia Peramelemorphia Notoryctemorphia Diprotodontia Subclass Placentalia Xenarthra Dermoptera Desmostylia Scandentia Primates Rodentia Lagomorpha Insectivora Chiroptera Pholidota Carnivora Perissodactyla Artiodactyla Cetacea Afrosoricida Macroscelidea Tubulidentata Hyracoidea Proboscidea Sirenia The mammals are the class of vertebrate animals primarily characterized by the presence of mammary... For other meanings of bird, see bird (disambiguation). ... Families   Acanthodrilidae   Ailoscolecidae   Alluroididae   Almidae   Criodrilidae   Eudrilidae   Exxidae   Glossoscolecidae   Lumbricidae   Lutodrilidae   Megascolecidae   Microchaetidae   Ocnerodrilidae   Octochaetidae   Sparganophilidae Earthworm is the common name for the hugest members of the Oligochaeta (which is either a class or subclass depending on the author) in the phylum Annelida. ... Orders See taxonomy Insects (Class Insecta) are a major group of arthropods and the most diverse group of animals on the Earth, with over a million described species—more than all other animal groups combined. ...

Certain surfactants used in some glyphosate formulations have have higher toxicity to Fish and invertebrates resulting in some formulations of glyphosate not being registered for use in aquatic applications.^[14] Monsanto produces Glyphosate products with alternative surfactants that are specifically formulate for aquatic use - eg "Biactive" and "AquaMaster".^[15]According to Monsanto "Conservation groups have chosen glyphosate formulations because of their effectiveness against most weeds as glyphosate has very low toxicity to wildlife".[20] A giant grouper at the Georgia Aquarium Fish are aquatic vertebrates that are typically cold-blooded; covered with scales, and equipped with two sets of paired fins and several unpaired fins. ... Invertebrate is a term that describes any animal without a spinal column. ...

When glyphosate comes into contact with the soil, it rapidly binds to soil particles and is inactivated.^[16][17] Unbound glyphosate is degraded by bacteria. Low activity because of binding to soil particles suggests that glyphosate's effects on soil flora will be limited. Low glyphosate concentrations can be found in many creeks and rivers in U.S. and Europe^{[citation needed]}. Soil texture triangle, showing the 12 major textural classes, and particle size scales. ... Soil flora and Soil fauna are terms used to describe the organisms that live within soils. ...

Mammalian research indicates oral intake of 1% glyphosate induces changes in liver enzyme activities in pregnant rats and their fetuses.[21][22] Subclasses Allotheria* Order Multituberculata (extinct) Order Volaticotheria (extinct) Order Palaeoryctoides (extinct) Order Triconodonta (extinct) Order Docodonta (extinct) Prototheria Order Monotremata Theria Infraclass Trituberculata (extinct) Infraclass Marsupialia Infraclass Eutheria The mammals are the class of vertebrate animals characterized by the production of milk in females for the nourishment of young, from... A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... Human fetus at eight weeks. ...

Use

Glyphosate is effective in killing a wide variety of plants, including grasses, broadleaf, and woody plants.^[10] It has a relatively small effect on clover.^{[citation needed]} 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] Natural vegetaton dominated by grasses Grass is a common word that generally describes a monocotyledonous green plant in the family Poaceae. ... Classes Magnoliopsida - Dicots Liliopsida - Monocots The flowering plants (also angiosperms or Magnoliophyta) are one of the major groups of modern plants, comprising those that produce seeds in specialized reproductive organs called flowers, where the ovulary or carpel is enclosed. ... Woody is used : In botany as an adjective to describe wood. ... Concern has been expressed that this article or section is missing information about: horticulture as used in anthropology, a label for agriculture as used in small-scale societies. ... Silviculture is the art and science of controlling the establishment, growth, composition, health, and quality of forests to meet diverse needs and values of landowners and society on a sustainable basis. ...

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 genetically modified crops was isolated from Agrobacterium strain CP4 (CP4 EPSPS) that was resistant to glyphosate.^[19][20] This CP4 EPSPS gene was cloned and transfected into soybeans, and in 1996, such genetically modified soybeans were made commercially available.^[21] This greatly improved the ability to control weeds in soybean fields 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.^[22][23] This article or section does not cite its references or sources. ... Species Agrobacterium tumefaciens Agrobacterium rhizogenes áAgrobacterium is a genus of bacteria that causes tumors in plants. ... Cloning is the process of creating an identical copy of something. ... Introducing DNA into eukaryotic cells, such as animal cells, is called transfection. ... Binomial name Glycine max Soybeans (US) or soya beans (UK) (Glycine max) are a high-protein legume (Family Fabaceae) grown as food for both humans and livestock. ... 1996 (MCMXCVI) was a leap year starting on Monday of the Gregorian calendar, and was designated the International Year for the Eradication of Poverty. ... This article does not cite its references or sources. ...

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.^[24] Binomial name Erythroxylum coca Lam. ... Plan Colombia is a controversial initiative aimed at resolving the ongoing, fifty-year civil war in Colombia. ... Massive mark-ups for drugs, UK Govt report Prevalance of drug use 1991-2006 The War on Drugs is an initiative undertaken by the United States with the assistance of participating countries, which is intended to combat the illegal drug trade —to curb supply and diminish demand for certain psychoactive...

Health concerns

There are concerns about the effects of glyphosate (and Roundup) on non-plant species even including on possible human reproductive dysfunction. For more information, see the Roundup article. Roundup is the brand name of a systemic, broad-spectrum herbicide produced by the U.S. life sciences giant Monsanto. ...

Endocrine disruptor debate

In vitro studies have shown glyphosate effects progesterone production in mammalian cells^[25] and can increase the mortality of placental cells.^[7] Whether these studies classify glyphosate as an endocrine disruptor is a matter of debate. Endocrine disruptors are substances which interfere with the endocrine system by mimicking, blocking or otherwise disrupting the function of hormones. ...

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.

References

1. ^ Murtaza F. Alibhai and William C. Stallings. Closing down on glyphosate inhibition—with a new structure for drug discovery [[Proceedings of the National Academy of Sciences|PNAS 2001, 98(6): 2944–2946. Online access via PubMed
2. ^ Technology Administration: National Medal of Technology RECIPIENTS
3. ^ People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry, The Scientist 1990, 4(10):28 John Franz's Perkin Medal
4. ^ ^{a b c d} 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.
5. ^ U.S. EPA ReRegistration Decision Fact Sheet for Glyphosate (EPA-738-F-93-011) 1993. [1]
6. ^ Nagami et al. (2005). Hospital-based survey of pesticide poisoning in Japan, 1998--2002. Int J Occup Environ Health, 11(2):180-4.PMID 15875894
7. ^ ^{a b} Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE. (2005) Differential effects of glyphosate and roundup on human placental cells and aromatase, Environmental Health Perspectives, 113 (6): 716-720. PMID 15929894 Full Text
8. ^ Goldstein DA et al An analysis of glyphosate data from the California Environmental Protection Agency Pesticide Illness Surveillance Program J Toxicol Clin Toxicol. 2002 40:885-92 [2]
9. ^ ^{a b} California EPA 1996, California Pesticide Illness Serveillance Program Report HS-1733 [3]
10. ^ ^{a b} Greenpeace. (1997). Weed Killing Crops: Glyphosate and Your Food.[4]
11. ^ JA Springett and RAJ Gray, Effect of repeated low doses of biocides on the earthworm Aporrectodea caliginosa in laboratory culture. Soil Biol and Biochem. Vol. 24, no. 12, pp. 1739-1744. 1992.[5]
12. ^ Hassan, S.A., F. Bigler, H. Bogenschutz, E. Boller, J. Brun, P. Chiverton, P. Edwards, F. Mansour, E. Naton, P.A. Oomen, W.P.J. Overmeer, L. Polgar, W. Rieckman, L. Samsoe-Petersen, A. Staubli, G. Sterk, K. Tavares, J.J. Tuset, G. Viggiani, and A.G. Vivas. 1988. Results of the fourth joint pesticide testing programme carried out by the IOBC/WPRS-Working Group
13. ^ 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.
14. ^ Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities", Monsanto Corporation Backgrounder [6]
15. ^ Aquatic Use of Glyphosate Herbicides in Australia, Monsanto Corporation Backgrounder[7]
16. ^ US EPA Reregistration Eligibility Decision - Glyphosate[8]
17. ^ M.M. de Andréa et al, Influence of repeated applications of glyphosate on its persistence and soil bioactivity Pesq. agropec. bras., Brasília, v. 38, n. 11, p. 1329-1335, nov. 2003[9]
18. ^ ^{a b} U.S. Environmental Protection Agency. (2006). Technical Factsheet on: GLYPHOSATE [10]
19. ^ Development and Characterization of a CP4 EPSPS-Based, Glyphosate-Tolerant Corn Event,G. R. Heck et al Crop Sci. 45:329-339 (2005).[11]
20. ^ Molecular basis for the herbicide resistance of Roundup Ready crops, T. Funke et al, PNAS 2006 103:13010-13015 [12]
21. ^ Monsanto Company History - Monsanto Web Site - monsanto.com[13]
22. ^ 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 [14]
23. ^ National Agriculture Statistics Service (2005) in Acreage eds. Johanns, M. & Wiyatt, S. D. 6 30, (U.S. Dept. of Agriculture, Washington, DC).
24. ^ IRC Americas Program Commentary (2005): Plan Colombia’s Drug Eradication Program Misses the Mark
25. ^ Walsh LP, et al (2000). "Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (stAR) protein expression.". Environmental Health Perspectives 108-N8: 769-776.[15]

• EU (2002). Review report for the active substance glyphosate. Retrieved October 28, 2005.
• JP Giesy, KR Solomon, S Dobson (2000). "Ecotoxicological Risk Assessment for Roundup Herbicide". Reviews of Environmental Contamination and Toxicology 167: 35-120. 
• 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. 
• World Health Organization. (1994) Environmental Health Criteria 159: Glyphosate. [23]
• Monsanto History of Glyphosate.[24]

Medline is a comprehensive literature database of life sciences and biomedical information. ... The National Medal of Technology is an honor granted by the President of the United States to inventors and innovators that have made significant contributions to the development of new and important technology. ... The Perkin Medal is an award given annually by the American section of the Society of Chemical Industry to a scientist residing in America for an innovation in applied chemistry resulting in outstanding commercial development. ...

External links

• 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
• Links to external chemical sources