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Revision as of 13:37, 26 January 2011 view sourceBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit Latest revision as of 06:24, 28 December 2024 view source Bon courage (talk | contribs)Extended confirmed users66,214 edits Restored revision 1265436281 by Tryptofish (talk): Rv. unreliable; would need WP:MEDRSTags: Twinkle Undo 
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{{short description|Systemic herbicide and crop desiccant}}
{{Distinguish|Glufosinate}}
{{about|the chemical alone|herbicides based on it|Glyphosate-based herbicides|the brand-name formulation developed by Monsanto|Roundup (herbicide)}}
{{pp|small=yes}}
{{Use mdy dates|date=March 2016}}
{{Use American English|date=May 2018}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 400108359
| Watchedfields = changed
| verifiedrevid = 443847907
| Name = Glyphosate | Name = Glyphosate
| pronounce = {{IPAc-en|ˈ|ɡ|l|ɪ|f|ə|s|eɪ|t|,_|ˈ|ɡ|l|aɪ|f|ə|-}},<ref>{{cite Merriam-Webster|glyphosate|access-date=June 28, 2020}}</ref> {{IPAc-en|ɡ|l|aɪ|ˈ|f|ɒ|s|eɪ|t}}<ref>{{cite Dictionary.com|glyphosate|access-date=June 28, 2020}}</ref><ref>{{cite American Heritage Dictionary|glyphosate|access-date=June 28, 2020}}</ref>
| ImageFile = Glyphosate-2D-skeletal.png
| ImageFile1 = Glyphosate.svg
| ImageSize =
| ImageClass1 = skin-invert
| ImageFile2 = Glyphosate-3D-balls.png
| ImageCaption1 = Idealised ] of the uncharged molecule
| IUPACName = ''N''-(phosphonomethyl)glycine
| ImageFile2 = Glyphosate-from-xtal-view-2-3D-bs-17.png
| OtherNames = 2-acetic acid
| ImageCaption2 = ] of the ] (charged form), based on the ]<ref name="PHOGLY05">{{ cite journal | url = https://doi.org/10.5517/ccdc.csd.cc2dmhvd | title = CSD Entry: PHOGLY05 | website = ]: Access Structures | year = 2022 | publisher = ] | doi = 10.5517/ccdc.csd.cc2dmhvd | access-date = 2023-11-04 | last1 = Wilson | first1 = C. J. G. | last2 = Wood | first2 = P. A. | last3 = Parsons | first3 = S. }}</ref><ref>{{ cite journal | first1 = Cameron J. G. | last1 = Wilson | first2 = Peter A. | last2 = Wood | first3 = Simon | last3 = Parsons | title = Discerning subtle high-pressure phase transitions in glyphosate | journal = ] | year = 2023 | volume = 25 | issue = 6 | pages = 988–997 | doi = 10.1039/D2CE01616H | doi-access = free | hdl = 20.500.11820/e81bbc4f-a6d1-4e16-a288-6eb9ff626485 | hdl-access = free }}</ref>
| Section1 = {{Chembox Identifiers
| IUPACName = ''N''-(Phosphonomethyl)glycine
| UNII_Ref = {{fdacite|correct|FDA}}
| SystematicName = acetic acid
| UNII = 4632WW1X5A
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 1071-83-6
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (free acid)
| CASNo1_Ref = {{cascite|changed|CAS}}
| CASNo1 = 38641-94-0
| CASNo1_Comment = (isopropylammonium salt)
| CASNo2_Ref = {{cascite|changed|CAS}}
| CASNo2 = 70393-85-0
| CASNo2_Comment = (sesquisodium salt)
| CASNo3_Ref = {{cascite|changed|CAS}}
| CASNo3 = 81591-81-3
| CASNo3_Comment = (] salt)<!-- 38641-94-0 also verified at CAS Common Chemistry, 70393-85-0 and 81591-81-3 verified at ESIS -->
| Beilstein = 2045054
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27744
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 95764
| DrugBank = DB04539
| EC_number = 213-997-4 <!-- 254-056-8 for isopropylammonium salt, 274-591-0 for sesquisodium salt -->
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3376
| Gmelin = 279222
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01705 | KEGG = C01705
| PubChem = 3496
| RTECS = MC1075000
| UNNumber = 3077 2783
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4632WW1X5A
| InChI = 1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9) | InChI = 1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
| InChIKey = XDDAORKBJWWYJS-UHFFFAOYAE | InChIKey = XDDAORKBJWWYJS-UHFFFAOYAE
| ChEMBL = 95764
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9) | StdInChI = 1S/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XDDAORKBJWWYJS-UHFFFAOYSA-N | StdInChIKey = XDDAORKBJWWYJS-UHFFFAOYSA-N
| SMILES = O=C(O)CNCP(=O)(O)O
| CASNo = 1071-83-6
| CASNo_Ref = {{cascite|correct|CAS}}
| CASOther = <br />38641-94-0 (isopropylammmonium salt)<br />70393-85-0 (sesquisodium salt)<br />81591-81-3 (] salt) <!-- 38641-94-0 also verified at CAS Common Chemistry, 70393-85-0 and 81591-81-3 verified at ESIS -->
| EC-number = 213-997-4 <!-- 254-056-8 for isopropylammmonium salt, 274-591-0 for sesquisodium salt -->
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3376
| RTECS = MC1075000
| PubChem = 3496
| SMILES = O=C(O)CNCP(=O)(O)O
}} }}
| Section2 = {{Chembox Properties |Section2 = {{Chembox Properties
| Reference = <ref name="EHC">{{EHC-ref|number=159|name=Glyphosate|date=1994|isbn=92-4-157159-4}}</ref> | Properties_ref = <ref name="EHC">{{EHC-ref|number=159|name=Glyphosate|date=1994|isbn=92-4-157159-4}}</ref>
| C = 3 | H = 8 | N = 1 | O = 5 | P = 1 | C=3 | H=8 | N=1 | O=5 | P=1
| Appearance = white crystalline powder | Appearance = white crystalline powder
| Density = 1.704 (20&nbsp;°C) | Density = 1.704 (20&nbsp;°C)
| MeltingPt = 184.5&nbsp;°C | MeltingPtC = 184.5
| BoilingPt_notes= decomposes
| BoilingPt = decomp. at 187&nbsp;°C
| Solubility = 1.01 g/100 mL (20&nbsp;°C) | BoilingPtC = 187
| Solubility = 1.01 g/100 mL (20&nbsp;°C)
| LogP = −2.8 | LogP = −2.8
| pKa = <2, 2.6, 5.6, 10.6 | pKa = <2, 2.6, 5.6, 10.6
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| Reference = <ref name="EHC"/><ref>{{CLP Regulation|index=607-315-00-8|pages=570, 1100}}</ref> | Hazards_ref = <ref name="EHC"/><ref>{{CLP Regulation|index=607-315-00-8|pages=570, 1100}}</ref>
| ExternalMSDS = | ExternalSDS =
| GHSPictograms = {{GHS05|Eye Dam. 1}}{{GHS09|Aquatic Chronic 2}}
| EUIndex = 607-315-00-8 <!-- 607-316-00-3 for trimethylsulfonium salt -->
| GHSSignalWord = DANGER
| EUClass = Irritant ('''Xi''')<br />Dangerous for the environment ('''N''')
| RPhrases = {{R41}}, {{R51/53}} | HPhrases = {{H-phrases|318|411}}
| PPhrases = {{P-phrases|273|280|305+351+338|310|501}}
| SPhrases = {{S2}}, {{S26}}, {{S39}}, {{S61}}
| FlashPt = Non-flammable
| GHSPictograms = {{GHS05|Eye Dam. 1}}{{GHS09|Aquatic Chronic 2}}
| GHSSignalWord = DANGER
| HPhrases = {{H-phrases|318|411}}
| PPhrases = {{P-phrases|273|280|305+351+338|310|501}}
| FlashPt = non-flammable
}} }}
}} }}
'''Glyphosate''' (N-(phosphonomethyl) glycine) is a broad-spectrum ] ] used to kill ]s, especially ]. It is typically sprayed and absorbed through the leaves, injected into the ], 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 ] in the 1970s under the tradename '']'', its U.S. ] expired in 2000. Glyphosate is the most used herbicide in the USA,<ref name="EPAusage">US EPA 2000–2001 Pesticide Market Estimates , </ref> where every year, 5–8 million pounds (2,300–3,600 tonnes) are used on lawns and yards and another 85–90 million pounds (39,000–41,000&nbsp;t) are used in agriculture.<ref name="EPAusage"/>


'''Glyphosate''' (]: '''''N''-(phosphonomethyl)glycine''') is a broad-spectrum ] and ]. It is an ], specifically a ], which acts by ] (EPSP). ] are used to kill ]s, especially annual ] and grasses that compete with ]s. Monsanto brought it to market for agricultural use in 1974 under the trade name ]. Monsanto's last commercially relevant United States ] expired in 2000.
Glyphosate's mode of action is to inhibit an ] involved in the synthesis of the ] ]s: ], ] and ]. 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 ].

Farmers quickly adopted glyphosate for agricultural weed control, especially after Monsanto introduced glyphosate-resistant ], enabling farmers to kill weeds without killing their crops. In 2007, glyphosate was the most used herbicide in the United States' agricultural sector and the second-most used (after ]) in home and garden, government and industry, and commercial applications.<ref name="EPAusage">{{cite web | title=2006-2007 Pesticide Market Estimates: Usage (Page 2) - Pesticides - US EPA | website=epa.gov | date=2011-02-18 | url=https://www.epa.gov/opp00001/pestsales/07pestsales/usage2007_2.htm#3_6 | archive-url=https://web.archive.org/web/20150626092432/https://www.epa.gov/opp00001/pestsales/07pestsales/usage2007_2.htm#3_6 | archive-date=2015-06-26 | url-status=dead | access-date=2021-11-30}}</ref> From the late 1970s to 2016, there was a 100-fold increase in the frequency and volume of application of ] (GBHs) worldwide, with further increases expected in the future.

Glyphosate is absorbed through foliage, and minimally through roots, and from there translocated to growing points. It inhibits ], a plant enzyme involved in the synthesis of three ]s: ], ], and ]. It is therefore effective only on actively growing plants and is not effective as a ]. Crops have been ] to be tolerant of glyphosate (e.g. ], the first Roundup Ready crop, also created by Monsanto), which allows farmers to use glyphosate as a post-emergence herbicide against weeds.

While glyphosate and formulations such as Roundup have been approved by regulatory bodies worldwide, concerns about their effects on humans and the environment have persisted.<ref name="biomedcentral_2016">{{cite journal | title=Concerns over use of glyphosate-based herbicides and risks associated with exposures: a consensus statement | journal=]| date=February 17, 2016 |first1=John Peterson |last1=Myers |first2=Michael N. |last2=Antoniou |first3=Bruce |last3=Blumberg |first4=Lynn |last4=Carroll |first5=Theo |last5=Colborn |first6=Lorne G. |last6=Everett |first7=Michael |last7=Hansen |first8=Philip J. |last8=Landrigan |first9=Bruce P. |last9=Lanphear |first10=Robin |last10=Mesnage |first11=Laura N. |last11=Vandenberg |first12=Frederick S. |last12=vom Saal |first13=Wade V. |last13=Welshons |first14=Charles M. |last14=Benbroo | name-list-style = vanc | pages=13 |doi=10.1186/s12940-016-0117-0 | pmid=26883814 |pmc = 4756530|volume=15 |number=19| bibcode=2016EnvHe..15...19M| doi-access=free}}</ref><ref name=NatureonWHO2015/> A number of regulatory and scholarly reviews have evaluated the relative toxicity of glyphosate as an herbicide. The WHO and ] Joint committee on pesticide residues issued a report in 2016 stating the use of glyphosate formulations does not necessarily constitute a health risk, and giving an ] limit of 1 milligram per kilogram of body weight per day for chronic toxicity.<ref>{{Cite web|url=https://www.who.int/foodsafety/jmprsummary2016.pdf|title=Report of the Joint Committee on Pesticide Residues, WHO/FAO, Geneva, 16 May, 2016}}</ref>

The ] among national pesticide regulatory agencies and scientific organizations is that labeled uses of glyphosate have demonstrated no evidence of human carcinogenicity.<ref name=Tarazona>{{cite journal |last1=Tarazona |first1=Jose V. |last2=Court-Marques |first2=Daniele |last3=Tiramani |first3=Manuela |last4=Reich |first4=Hermine |last5=Pfeil |first5=Rudolf |last6=Istace |first6=Frederique |last7=Crivellente |first7=Federica |title=Glyphosate toxicity and carcinogenicity: a review of the scientific basis of the European Union assessment and its differences with IARC |journal=]|date=3 April 2017 |volume=91 |issue=8 |pages=2723–43 |doi=10.1007/s00204-017-1962-5 |pmid=28374158 |pmc=5515989 |bibcode=2017ArTox..91.2723T }}</ref> In March 2015, the ]'s ] (IARC) classified glyphosate as "probably carcinogenic in humans" (]) based on epidemiological studies, animal studies, and '']'' studies.<ref name="NatureonWHO2015" /><ref name="Lancet20March2015">{{cite journal | vauthors = Guyton KZ, Loomis D, Grosse Y, El Ghissassi F, Benbrahim-Tallaa L, Guha N, Scoccianti C, Mattock H, Straif K | title = Carcinogenicity of tetrachlorvinphos, parathion, malathion, diazinon, and glyphosate | journal =]| volume = 16 | issue = 5 | pages = 490–91 | date = May 2015 | pmid = 25801782 | doi = 10.1016/S1470-2045(15)70134-8 }}</ref><ref name="IARC20March2015" /><ref name="iarcmono">{{cite journal | url = https://monographs.iarc.fr/wp-content/uploads/2018/06/mono112-10.pdf | title = Glyphosate | journal = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans | volume = 112 | date = 11 August 2016 | publisher = ] | access-date = July 31, 2019 | archive-date = July 30, 2019 | archive-url = https://web.archive.org/web/20190730162330/https://monographs.iarc.fr/wp-content/uploads/2018/06/mono112-10.pdf | url-status = dead }}</ref> In contrast, the ] concluded in November 2015 that "the substance is unlikely to be ] (i.e. damaging to ]) or to pose a ]ic threat to humans", later clarifying that while carcinogenic glyphosate-containing formulations may exist, studies that "look solely at the active substance glyphosate do not show this effect".<ref>{{Cite web|url=https://www.efsa.europa.eu/sites/default/files/corporate_publications/files/efsaexplainsglyphosate151112en.pdf|title=European Food Safety Authority – Glyphosate report|website=]|access-date=May 23, 2016}}</ref><ref>{{Cite web|url=http://www.efsa.europa.eu/en/press/news/151112|title=Glyphosate: EFSA updates toxicological profile|website=] |access-date=2016-05-23|date=November 12, 2015}}</ref> In 2017, the ] (ECHA) classified glyphosate as causing serious eye damage and as toxic to aquatic life but did not find evidence implicating it as a carcinogen, a mutagen, toxic to reproduction, nor toxic to specific organs.<ref>{{cite web|url=https://echa.europa.eu/-/glyphosate-not-classified-as-a-carcinogen-by-echa|title=Glyphosate not classified as a carcinogen by ECHA|date=15 March 2017 |publisher=ECHA}}</ref>

==Discovery==
Glyphosate was first synthesized in 1950 by Swiss chemist Henry Martin, who worked for the Swiss company ]. The work was never published.<ref name=Dill>{{cite book | editor-last1 = Nandula | editor-first1 = Vijay K. | title = Glyphosate Resistance in Crops and Weeds: History, Development, and Management | first1 = Gerald M. | last1 = Dill | first2 = R. Douglas | last2 = Sammons | first3 = Paul C. | last3 = Feng | first4 = Frank | last4 = Kohn | first5 = Keith | last5 = Kretzmer | first6 = Akbar | last6 = Mehrsheikh | first7 = Marion | last7 = Bleeke | first8 = Joy L. | last8 = Honegger | first9 = Donna | last9 = Farmer | first10 = Dan | last10 = Wright | first11 = Eric A. | last11 = Haupfear | name-list-style = vanc | chapter = Glyphosate: Discovery, Development, Applications, and Properties | chapter-url = http://media.johnwiley.com.au/product_data/excerpt/10/04704103/0470410310.pdf | date = 2010 | publisher =]| location =]| isbn = 978-0-470-41031-8 }}</ref>{{rp|1}} Early studies found it to be a weak chemical ].<ref name="Casida-2017" /><ref>{{cite journal|title=Comments for Mertens et al. (2018), Glyphosate, a chelating agent—relevant for ecological risk assessment?|first1=John T.|last1=Swarthout|first2=Marian S.|last2=Bleeke|first3=John L.|last3=Vicini|journal=Environmental Science and Pollution Research International|date=June 16, 2018|volume=25|issue=27|pages=27662–3|doi=10.1007/s11356-018-2506-0|pmc=6132386|pmid=29907899|bibcode=2018ESPR...2527662S }}</ref>

Glyphosate was independently discovered in the ] at ] in 1970. About 100 ] of ] had been prepaared as potential ] agents. Two were found to have weak herbicidal activity, and ], a chemist at Monsanto, was asked to try to make analogs with stronger herbicidal activity. Glyphosate was the third analog he made.<ref name=Dill/>{{rp|1–2}}<ref name="pmid11248008">{{cite journal | vauthors = Alibhai MF, Stallings WC | title = Closing down on glyphosate inhibition&nbsp;– with a new structure for drug discovery | journal =]| volume = 98 | issue = 6 | pages = 2944–46 | date = Mar 2001 | pmid = 11248008 | pmc = 33334 | doi = 10.1073/pnas.061025898 | bibcode = 2001PNAS...98.2944A | jstor = 3055165 | doi-access = free }}</ref><ref>{{cite journal|title=Monsanto's John E. Franz Wins 1990 Perkin Medal|journal=]|date=12 March 1990|volume=68|issue=11|pages=29–30|doi=10.1021/cen-v068n011.p029 }}</ref> Franz received the ] of the United States in 1987 and the ] for Applied Chemistry in 1990 for his discoveries.<ref name="urlThe National Medal of Technology and Innovation Recipients – 1987">{{cite web | url = http://www.uspto.gov/about/nmti/recipients/1987.jsp | title = The National Medal of Technology and Innovation Recipients – 1987 | publisher = The ]| access-date = 2012-11-29 }}</ref><ref>{{cite journal | title = People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry | journal =]| vauthors = Stong C | date = May 1990 | volume = 4 | issue = 10 | pages = 28 | url = http://classic.the-scientist.com/?articles.view/articleNo/11141/|archive-url=https://web.archive.org/web/20140416133120/http://classic.the-scientist.com/?articles.view/articleNo/11141/title/People--Monsanto-Scientist-John-E--Franz-Wins-1990-Perkin-Medal-For-Applied-Chemistry/|url-status=dead|archive-date=2014-04-16 }}</ref><ref name="SCI Perkin Medal">{{cite web|title=SCI Perkin Medal|url=https://www.sciencehistory.org/sci-perkin-medal|website=]|access-date=24 March 2018|date=May 31, 2016}}</ref>

Monsanto developed and patented the use of glyphosate to kill weeds in the early 1970s and first brought it to market in 1974 under the Roundup brandname.<ref name="Duke" /><ref name="monsantofaq">{{cite web | url=https://monsanto.com/app/uploads/2017/06/back_history.pdf | title=History of Monsanto's Glyphosate Herbicides | publisher=]| access-date=20 December 2015 | archive-date=August 7, 2018 | archive-url=https://web.archive.org/web/20180807095908/https://monsanto.com/app/uploads/2017/06/back_history.pdf | url-status=dead }}</ref> While its initial patent<ref>{{cite patent| country = US| number = 3799758 | status = application| title = N-phosphonomethyl-glycine phytotoxicant compositions | pubdate = 1974-03-26| fdate = 1971-08-09| pridate = 1971-08-09| invent1 = John E. Franz| assign1 = Monsanto Company}}</ref> expired in 1991, Monsanto retained exclusive rights in the United States until its patent<ref>{{cite patent| country = US| number = 4405531 | status = application| title = Salts of N-phosphonomethylglycine| pubdate = 1983-09-20| fdate = 1982-03-08| pridate = 1975-11-10| invent1 = John E. Franz| assign1 = Monsanto Company}}</ref> on the isopropylamine salt expired in September 2000.<ref>{{cite web |url=http://www.frost.com/prod/servlet/market-insight-print.pag?docid=JEVS-5N2CZG |title=The Glyphosate Market: A 'Roundup' |last1=Fernandez |first1=Ivan |date=2002-05-15 |website=]|access-date=2015-03-10 |archive-url=https://web.archive.org/web/20160304085158/http://www.frost.com/prod/servlet/market-insight-print.pag?docid=JEVS-5N2CZG |archive-date=2016-03-04}}</ref>

In 2008, scientists at the United States Department of Agriculture ] (USDA ARS) described glyphosate as a "virtually ideal" herbicide.<ref name=Duke>{{citation |first1=Stephen O. |last1=Duke |first2=Stephen B. |last2=Powles |name-list-style=vanc |date=2008 |url=http://naldc.nal.usda.gov/download/17918/PDF |format=PDF |title=Glyphosate: a once-in-a-century herbicide: Mini-review |journal=]|volume=64 |issue=4 |pages=319–25 |doi=10.1002/ps.1518 |pmid=18273882 |access-date=April 13, 2014 |archive-date=July 2, 2019 |archive-url=https://web.archive.org/web/20190702211642/https://naldc.nal.usda.gov/download/17918/PDF |url-status=dead }}</ref> In 2010 Powles stated: "glyphosate is a one in a 100-year discovery that is as important for reliable global food production as penicillin is for battling disease."<ref name="PNAS_2010_Powles">{{cite journal | vauthors = Powles SB | title = Gene amplification delivers glyphosate-resistant weed evolution | journal =]| volume = 107 | issue = 3 | pages = 955–56 | date = January 2010 | pmid = 20080659 | pmc = 2824278 | doi = 10.1073/pnas.0913433107| bibcode = 2010PNAS..107..955P | doi-access = free }}</ref>

As of April 2017, the Canadian government stated that glyphosate was "the most widely used herbicide in Canada",<ref name=pmrare/> at which date the product labels were revised to ensure a limit of 20% ] by weight.<ref name=pmrare>{{cite web|url=https://www.canada.ca/en/health-canada/services/consumer-product-safety/reports-publications/pesticides-pest-management/fact-sheets-other-resources/request-special-review-glyphosate-herbicides-containing-polyethoxylated-tallowamine/frequently-asked-questions.html|title=Frequently Asked Questions on the Re-evaluation of Glyphosate|publisher=]|date=28 Apr 2017|access-date=10 May 2018}}</ref>{{failed verification|date=October 2020}} ]'s ] found no risk to humans or the environment at that 20% limit, and that all products registered in ] at that time were at or below that limit.

==Chemistry==
]
Glyphosate is a derivative of ] and the amino acid ]. Both the ] and ] moieties can ionised (deprotonated) and the ] group can be protonated. Consequently the substance exists as a series of rapidly interchanging ]s. It was originally synthesized by the reaction of chloromethyl] with glycine. Its name is a contraction of its constituents: '''gly'''cine and a '''phos'''phon'''ate'''.<ref name = Chenier>{{cite book|url = https://books.google.com/books?id=gbHeBwAAQBAJ&q=industrial+synthesis+glyphosate&pg=PA384|title = Survey of Industrial Chemistry|author = Chenier, Philip J.|page = 384|year = 2012|publisher = ]|edition = 3rd|isbn = 978-1461506034}}</ref>

:{{chem2|(HO)2P(O)CH2Cl + H2NCH2COOH → (HO)2P(O)CH2NHCH2COOH + HCl}}

The main degradation path for glyphosate is hydrolysis to ].<ref name="urlwww.cdpr.ca.gov">{{cite web | url = http://www.cdpr.ca.gov/docs/emon/pubs/fatememo/glyphos.pdf | title = Environmental Fate of Glyphosate | vauthors = Schuette J | publisher = Department of Pesticide Regulation, State of California | access-date = June 4, 2012 | archive-url = https://web.archive.org/web/20120420013222/http://www.cdpr.ca.gov/docs/emon/pubs/fatememo/glyphos.pdf | archive-date = April 20, 2012 | url-status = dead }}</ref>

===Synthesis===
Two main approaches are used to synthesize glyphosate industrially, both of which proceed via the ]. The first is to react ] and ] with ] (sometimes formed ''in situ'' from ] using the water generated by the ] of the first two reagents). ] of the ] product gives the desired glyphosate product. Iminodiacetic acid is usually prepared on-site by various methods depending on reagent availability.<ref name = Dill />

] approach to glyphosate synthesis]]

The second uses ] in place of iminodiacetic acid. This avoids the need for decarboxylation but requires more careful control of ], as the primary amine can react with any excess formaldehyde to form bishydroxymethylglycine, which must be hydrolysed during the ] to give the desired product.<ref name = Dill />

]

This synthetic approach is responsible for a substantial portion of the production of glyphosate in China, with considerable work having gone into recycling the triethylamine and methanol solvents.<ref name = Dill /> Progress has also been made in attempting to eliminate the need for triethylamine altogether.<ref>{{cite journal|title = Study on a New Synthesis Approach of Glyphosate | vauthors = Zhou J, Li J, An R, Yuan H, Yu F | journal = ]|year = 2012|volume = 60|issue = 25|pages = 6279–85|doi = 10.1021/jf301025p| pmid = 22676441 }}</ref>

===Impurities===
Technical grade glyphosate is a white powder which, according to ] specification, should contain not less than 95% glyphosate. ], classified as a known human carcinogen,
<ref name="IARC2006">{{cite book |last1=International Agency for Research on Cancer |title=IARC Monographs on the Evaluation of Carcinogenic Risks to Humans Volume 88: Formaldehyde, 2-Butoxyethanol and 1-''tert''-Butoxypropan-2-ol. |date=2006 |publisher=IARC/WHO |location=Lyon |url=http://monographs.iarc.fr/ENG/Monographs/vol88/index.phpExit|isbn=978-9283212881 }}</ref>
<ref name="NTP2011">{{cite book |last1=National Toxicology Program |title=Report on Carcinogens |date=June 2011 |publisher=Department of Health and Human Services, Public Health Service, National Toxicology Program |edition= 12th }}</ref>
and ], have been identified as toxicologically relevant impurities.<ref name="ImpuritiesFAO2014">{{cite book |last1=FAO |title=FAO specifications and evaluations for agricultural pesticides: glyphosate |date=2014 |publisher=. Food and Agriculture Organization of the United Nations |page=5 |url=http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/Specs/Glypho_2014.pdf}}</ref> The FAO specification limits the formaldehyde concentration to a maximum of 1.3 g/kg glyphosate. ''N''-Nitrosoglyphosate, "belonging to a group of impurities of particular concern as they can be activated to genotoxic carcinogens",<ref name="ESFApeerRev2015">{{cite journal |last1=European Food Safety Authority |title=Conclusion on the peer review of the pesticide risk assessment of the active substance glyphosate |journal= EFSA Journal|date=2015 |volume=13 |issue=11:4302 |page=10 |doi=10.2903/j.efsa.2015.4302 |doi-access=free }}</ref> should not exceed 1 ppm.<ref name = "ImpuritiesFAO2014"/>

==Formulations==
{{Main|Glyphosate-based herbicides}}
] is the earliest formulation]]
<!-- proprietary? {{Expand section|1=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? |date=September 2012}} -->Glyphosate is marketed in the United States and worldwide by many ] companies in diverse strengths and with diverse ], under dozens of tradenames.<ref>Farm Chemicals International </ref><ref name=AlbertaQuick2015/><ref name="urlISU Weed Science Online – Glyphosate – A Review">{{cite web | url = http://www.weeds.iastate.edu/mgmt/2001/glyphosate%20review.htm#Glyphosate%20Products | series = ISU Weed Science Online | title = Glyphosate: a Review | last1 = Hartzler | first1 = Bob | publisher =]| access-date = August 26, 2012 | archive-url = https://web.archive.org/web/20180518051215/http://www.weeds.iastate.edu/mgmt/2001/glyphosate%20review.htm#Glyphosate%20Products | archive-date = May 18, 2018 | url-status = dead }}</ref><ref name="Weed Handbook Glyphosate">{{cite web | url = http://www.invasive.org/gist/products/handbook/14.Glyphosate.pdf | title = Glyphosate | vauthors = Tu M, Hurd C, Robison R, Randall JM | date = November 1, 2001| work = Weed Control Methods Handbook | publisher = The Nature Conservancy }}</ref> As of 2010, more than 750 glyphosate products were on the market.<ref>National Pesticide Information Center. Last updated September 2010 </ref> In 2012, about half of the total global consumption of glyphosate by volume was for agricultural crops,<ref name=ReuterMarkets2014/> with ] comprising another important market.<ref> {{Webarchive|url=https://web.archive.org/web/20160407094242/http://www.monsanto.ca/products/Documents/vision_label_en.pdf |date=April 7, 2016 }}, 03-FEB-2011</ref> Asia and the Pacific was the largest and fastest growing regional market.<ref name="ReuterMarkets2014">{{cite news|url=https://www.reuters.com/article/2014/04/30/research-and-markets-idUSnBw306202a+100+BSW20140430|title=Press Release: Research and Markets: Global Glyphosate Market for Genetically Modified and Conventional Crops 2013–2019|date=30 April 2014|work=Reuters|url-status=dead|archive-url=https://web.archive.org/web/20150924200327/https://www.reuters.com/article/2014/04/30/research-and-markets-idUSnBw306202a+100+BSW20140430|archive-date=September 24, 2015|df=mdy-all}}</ref> As of 2014, Chinese manufacturers collectively are the world's largest producers of glyphosate and its precursors<ref>China Research & Intelligence, June 5, 2013. {{Webarchive|url=https://web.archive.org/web/20160303222042/http://www.shcri.com/agricultural-chemicals/14-research-report-on-global-and-china-glyphosate-industry-2013-2017.html |date=March 3, 2016 }}</ref> and account for about 30% of global exports.<ref name=ReuterMarkets2014/> Key manufacturers include Anhui Huaxing Chemical Industry Company, ], ] (which also acquired the maker of glyphosate, ]), ], ], Jiangsu Good Harvest-Weien Agrochemical Company, Nantong Jiangshan Agrochemical & Chemicals Co., ], SinoHarvest, ], and Zhejiang Xinan Chemical Industrial Group Company.<ref name=ReuterMarkets2014/>

Glyphosate is an acid molecule, so it is formulated as a ] for packaging and handling. Various salt formulations include isopropylamine, diammonium, monoammonium, or potassium as the ]. The ] of the Monsanto herbicides is the ] ] of glyphosate. Another important ingredient in some formulations is the ] ]. 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. Given that each salt has its own molecular weight, the acid equivalent is a more accurate method of expressing and comparing concentrations.

Adjuvant loading refers to the amount of adjuvant<ref name="Tu_Randall_2003">{{cite web | url = http://www.invasive.org/gist/products/handbook/14.Glyphosate.pdf | title = Glyphosate | vauthors = Tu M, Randall JM | date = 2003-06-01 | work = Weed Control Methods Handbook | publisher = The Nature Conservancy }}</ref><ref name="urlCrops and Soils – Penn State Extension">{{cite web | url = http://extension.psu.edu/pests/weeds/control/adjuvants-for-enhancing-herbicide-performance | title = Adjuvants for Enhancing Herbicide Performance | vauthors = Curran WS, McGlamery MD, Liebl RA, Lingenfelter DD | year = 1999 | publisher =Penn State Extension }}</ref> already added to the glyphosate product. Fully loaded products contain all the necessary adjuvants, including ]; 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.<ref name=UDelFormulations>{{cite web | url = http://agdev.anr.udel.edu/weeklycropupdate/?p=96 | title = Glyphosate Formulations | vauthors = VanGessel M | work = Control Methods Handbook, Chapter 8, Adjuvants: Weekly Crop Update | publisher = University of Delaware Cooperative Extension | access-date = August 27, 2012 | archive-url = https://web.archive.org/web/20100613014135/http://agdev.anr.udel.edu/weeklycropupdate/?p=96 | archive-date = June 13, 2010 | url-status = dead }}</ref>

Products are supplied most commonly in formulations of 120, 240, 360, 480, and 680&nbsp;g/L of active ingredient. The most common formulation in agriculture is 360&nbsp;g/L, either alone or with added ]s.<ref name=AlbertaQuick2015>Alberta Agriculture and Rural Development. April 26, 2006. {{Webarchive|url=https://web.archive.org/web/20170726123020/http://www1.agric.gov.ab.ca/$department/deptdocs.nsf/all/faq8069 |date=July 26, 2017 }}</ref>

For {{Convert|360|g/L}} formulations, European regulations allow applications of up to {{Convert|12|L/ha}} for control of perennial weeds such as ]. More commonly, rates of {{Convert|3|L/ha}} are practiced for control of annual weeds between crops.<ref>{{cite web|url=http://e-phy.agriculture.gouv.fr/|title=e-phy|website=e-phy.agriculture.gouv.fr}}</ref>

==Mode of action==
Glyphosate interferes with the ], which produces the ] ], ] and ] in plants and microorganisms<ref name="Funke_2006">{{cite journal | vauthors = Funke T, Han H, Healy-Fried ML, Fischer M, Schönbrunn E | title = Molecular basis for the herbicide resistance of Roundup Ready crops | journal =]| volume = 103 | issue = 35 | pages = 13010–15 | date = Aug 2006 | pmid = 16916934 | pmc = 1559744 | doi = 10.1073/pnas.0603638103 | bibcode = 2006PNAS..10313010F| jstor = 30050705 | doi-access = free }}</ref> – but does not exist in the genome of animals, including humans.<ref name="pmid22554242">{{cite journal | vauthors = Maeda H, Dudareva N | title = The shikimate pathway and aromatic amino Acid biosynthesis in plants | journal =]| volume = 63 | pages = 73–105 | year = 2012 | issue = 1 | pmid = 22554242 | doi = 10.1146/annurev-arplant-042811-105439 | quote = The AAA pathways consist of the shikimate pathway (the prechorismate pathway) and individual postchorismate pathways leading to Trp, Phe, and Tyr.... These pathways are found in bacteria, fungi, plants, and some protists, but are absent in animals. Therefore, AAAs and some of their derivatives (vitamins) are essential nutrients in the human diet, although in animals Tyr can be synthesized from Phe by Phe hydroxylase....The absence of the AAA pathways in animals also makes these pathways attractive targets for antimicrobial agents and herbicides. }}</ref><ref name="Casida-2017">{{cite journal | last=Casida | first=John E. | title=Organophosphorus Xenobiotic Toxicology | journal=] | publisher=] | volume=57 | issue=1 | date=2017-01-06 | issn=0362-1642 | doi=10.1146/annurev-pharmtox-010716-104926 | pages=309–327| pmid=28061690 | doi-access=free }}</ref> It blocks this pathway by inhibiting the enzyme ] (EPSPS), which ] the reaction of ]-3-phosphate (S3P) and ] to form 5-enolpyruvyl-shikimate-3-phosphate (EPSP).<ref name="pmid7396959">{{cite journal | vauthors = Steinrücken HC, Amrhein N | title = The herbicide glyphosate is a potent inhibitor of 5-enolpyruvyl-shikimic acid-3-phosphate synthase | journal =]| volume = 94 | issue = 4 | pages = 1207–12 | date = Jun 1980 | pmid = 7396959 | doi = 10.1016/0006-291X(80)90547-1 }}</ref> Glyphosate is absorbed through foliage and minimally through roots, meaning that it is only effective on actively growing plants and cannot prevent seeds from germinating.<ref name="NPIC Data Sheet"/><ref name=moneuro/> After application, glyphosate is readily transported around the plant to growing roots and leaves and this ] activity is important for its effectiveness.<ref name=Duke/><ref name=Dill/> Inhibiting the enzyme causes shikimate to accumulate in plant tissues and diverts energy and resources away from other processes, eventually killing the plant. While growth stops within hours of application, it takes several days for the leaves to begin ].<ref name=hock04>{{cite book | first1 = Bertold | last1 = Hock | first2 = Erich F. | last2 = Elstner | name-list-style = vanc | title = Plant Toxicology, Fourth Edition | url = https://books.google.com/books?id=pWqBJpWnK4EC&pg=PA292 | year= 2004 | publisher=CRC Press | isbn = 978-0-203-02388-4 | pages = 292–96 }}</ref> Glyphosate may chelate ] which contributes to its mode of action.<ref name="Shick-Dunlap-2002">{{cite journal | last1=Shick | first1=J. Malcolm | last2=Dunlap | first2=Walter C. | title=Mycosporine-Like Amino Acids and Related Gadusols: Biosynthesis, Accumulation, and UV-Protective Functions in Aquatic Organisms | journal=] | publisher=] | volume=64 | issue=1 | year=2002 | issn=0066-4278 | doi=10.1146/annurev.physiol.64.081501.155802 | pages=223–262| pmid=11826269 }}</ref><ref name="Kishore-Shah-1988">{{cite journal | last1=Kishore | first1=Ganesh M. | last2=Shah | first2=Dilip M. | title=Amino Acid Biosynthesis Inhibitors as Herbicides | journal=] | publisher=] | volume=57 | issue=1 | year=1988 | issn=0066-4154 | doi=10.1146/annurev.bi.57.070188.003211 | pages=627–663| pmid=3052285 }}</ref><ref name="Bentley-Haslam-1990">{{cite journal | last1=Bentley | first1=Ronald | last2=Haslam | first2=E. | title=The Shikimate Pathway — A Metabolic Tree with Many Branches | journal=] | publisher=] | volume=25 | issue=5 | year=1990 | issn=1040-9238 | doi=10.3109/10409239009090615 | pages=307–384 | pmid=2279393 | s2cid=1667907}}</ref>

]

Under normal circumstances, EPSP is ] to ], an essential precursor for the amino acids mentioned above.<ref>Purdue University, Department of Horticulture and Landscape Architecture, Metabolic Plant Physiology Lecture notes, {{Webarchive|url=https://web.archive.org/web/20071219165155/http://www.hort.purdue.edu/rhodcv/hort640c/aromat/ar00007.htm |date=December 19, 2007 }}.</ref> These amino acids are used in protein synthesis and to produce secondary metabolites such as ]s, ]s, and ].

] 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–substrate complex.<ref name="pmid11171958">{{cite journal | vauthors = Schönbrunn E, Eschenburg S, Shuttleworth WA, Schloss JV, Amrhein N, Evans JN, Kabsch W | title = Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail | journal =]| volume = 98 | issue = 4 | pages = 1376–80 | date = Feb 2001 | pmid = 11171958 | pmc = 29264 | doi = 10.1073/pnas.98.4.1376 | bibcode = 2001PNAS...98.1376S | doi-access = free }}</ref><ref> in the Protein Data Bank</ref> Glyphosate inhibits the EPSPS enzymes of diverse species of plants and microbes, although rates vary.<ref>{{cite journal | last1 = Schulz | first1 = A. | last2 = Krüper | first2 = A. | last3 = Amrhein | first3 = N. | name-list-style = vanc | year = 1985 | title = Differential sensitivity of bacterial 5-enolpyruvylshikimate-3-phosphate synthases to the herbicide glyphosate | journal =]| volume = 28 | issue = 3| pages = 297–301 | doi=10.1111/j.1574-6968.1985.tb00809.x| doi-access = free }}</ref><ref name="Pollegioni_2011">{{cite journal | vauthors = Pollegioni L, Schonbrunn E, Siehl D | title = Molecular basis of glyphosate resistance-different approaches through protein engineering | journal = The FEBS Journal| volume = 278 | issue = 16 | pages = 2753–66 | date = Aug 2011 | pmid = 21668647 | pmc = 3145815 | doi = 10.1111/j.1742-4658.2011.08214.x }}</ref>

==Uses==
]
Glyphosate is effective in killing a wide variety of plants, including ]es and ] and ]s. By volume, it is one of the most widely used herbicides.<ref name="NPIC Data Sheet">{{cite web|url=http://npic.orst.edu/factsheets/glyphotech.html|publisher=National Pesticide Information Center|title=Glyphosate technical fact sheet (revised June 2015)|year=2010|access-date=September 1, 2015|archive-url=https://web.archive.org/web/20150828151524/http://npic.orst.edu/factsheets/glyphotech.html|archive-date=August 28, 2015|url-status=bot: unknown}}</ref> In 2007, glyphosate was the most used herbicide in the United States agricultural sector, with 180 to 185 million pounds ({{convert|180000000|to|185000000|lb|t|abbr=off|disp=output only}}) applied, the second-most used in home and garden with 5 to 8 million pounds ({{convert|5000000|to|8000000|lb|t|abbr=off|disp=output only}}) and 13 to 15 million pounds ({{convert|13000000|to|15000000|lb|t|abbr=off|disp=output only}}) in non-agricultural settings.<ref name="EPAusage"/> It is commonly used for ], ], ], and ] purposes, as well as garden maintenance (including home use). It has a relatively small effect on some clover species and ].<ref>{{cite web | first1 = Stevan Z. | last1 = Knezevic | name-list-style = vanc | publisher =] Integrated Weed Management Specialist | date = February 2010 | url = http://elkhorn.unl.edu/epublic/live/g1484/build/ | archive-url = https://archive.today/20100615033810/http://elkhorn.unl.edu/epublic/live/g1484/build/ | archive-date=June 15, 2010| url-status = dead | title = Use of Herbicide-Tolerant Crops as Part of an Integrated Weed Management Program}}</ref>

]
Glyphosate and related herbicides are often used in ] eradication and ], especially to enhance ] establishment in ] ecosystems. The controlled application is usually combined with a selective herbicide and traditional methods of weed eradication such as ]ing to achieve an optimal effect.<ref>{{ cite journal | first1 = Priscilla A. | last1 = Nyamai | first2 = Timothy S. | last2 = Prather | first3 =John M. | last3 = Wallace | name-list-style = vanc | year = 2011 | title = Evaluating Restoration Methods across a Range of Plant Communities Dominated by Invasive Annual Grasses to Native Perennial Grasses | journal =]| volume = 4 | issue = 3 | pages = 306–16 | doi = 10.1614/IPSM-D-09-00048.1 | s2cid = 84696972 }}</ref>

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.<ref>{{cite journal |vauthors=Luijendijk CD, Beltman WH, Smidt RA, van der Pas LJ, Kempenaar C | url = http://www.wageningenur.nl/upload_mm/f/d/9/042e8dca-ba43-4687-99f0-fa082db417f1_Nota_353_totaal.pdf | title = Measures to reduce glyphosate runoff from hard surfaces | journal =]| location = Wageningen | date = May 2005}}</ref> Glyphosate contamination of surface water is attributed to urban and agricultural use.<ref name="pmid19482331">{{cite journal | vauthors = Botta F, Lavison G, Couturier G, Alliot F, Moreau-Guigon E, Fauchon N, Guery B, Chevreuil M, Blanchoud H | title = Transfer of glyphosate and its degradate AMPA to surface waters through urban sewerage systems | journal =]| volume = 77 | issue = 1 | pages = 133–39 | date = Sep 2009 | pmid = 19482331 | doi = 10.1016/j.chemosphere.2009.05.008 | bibcode = 2009Chmsp..77..133B }}</ref> Glyphosate is used to clear ]s and get rid of unwanted aquatic vegetation.<ref name=moneuro/> Since 1994, glyphosate has been used in aerial spraying in Colombia in ] programs; Colombia announced in May 2015 that by October, it would cease using glyphosate in these programs due to concerns about human toxicity of the chemical.<ref name = BBCColumbia>]. May 10, 2015. </ref>

Glyphosate is also used for ] to increase harvest yield and uniformity.<ref name=moneuro>{{cite web | url = https://monsanto.com/app/uploads/2017/06/agronomic-benefits-of-glyphosate-in-europe.pdf | title = The agronomic benefits of glyphosate in Europe | publisher = ] Europe SA | date = February 2010 | access-date = 2013-06-02 | archive-date = September 4, 2017 | archive-url = https://web.archive.org/web/20170904155703/https://monsanto.com/app/uploads/2017/06/agronomic-benefits-of-glyphosate-in-europe.pdf | url-status = dead }}</ref> Glyphosate itself is not a chemical ]; rather crop desiccants are so named because application just before harvest kills the crop plants so that the food crop dries from normal environmental conditions ("dry-down") more quickly and evenly.<ref>{{cite web |last1=MacLean |first1=Amy-Jean |title=Desiccant vs. Glyphosate: know your goals |url=https://www.portageonline.com/ag/desiccant-vs-glyphosate-know-your-goals |website=PortageOnline.com |publisher=]|access-date=19 August 2016 |archive-url=https://web.archive.org/web/20190731205820/https://www.portageonline.com/ag/desiccant-vs-glyphosate-know-your-goals |archive-date=31 July 2019 |language=en}}</ref>{{refn|In agriculture, the term desiccant is applied to an agent that promotes dry down. "True desiccants" are not chemical desiccants either, rather the distinction is whether an agent is a contact herbicide such as ] and ] that rapidly kill the above-ground portion of the plant as it dries out over a few days,<ref>{{cite web |title=Crop Desiccation |url=https://saifood.ca/crop-desiccation/ |website=Sustainable Agricultural Innovations & Food |publisher=]|access-date=31 July 2019 |archive-url=https://web.archive.org/web/20190731214944/https://saifood.ca/crop-desiccation/ |archive-date=31 July 2019 |language=en-CA |date=25 October 2016}}</ref> or an agent such as glyphosate that is absorbed systemically and translocated to the root, a process that can take days to weeks.}} Because glyphosate is systemic, excess residue levels can persist in plants due to incorrect application and this may render the crop unfit for sale.<ref>{{cite web|last1=Sprague|first1=Christy|title=Preharvest herbicide applications are an important part of direct-harvest dry bean production| url=http://msue.anr.msu.edu/news/preharvest_herbicide_applications_are_an_important_part_of_direct_harvest_d|website=]|date=August 20, 2015 |publisher=], Department of Plant, Soil and Microbial Sciences|access-date=20 August 2015}}</ref> When applied appropriately, it can promote useful effects. In sugarcane, for example, glyphosate application increases sucrose concentration before harvest.<ref name="LSUAgExt">{{cite web |last1=Gravois |first1=Kenneth |title=Sugarcane Ripener Recommendations |url=https://www.lsuagcenter.com/topics/crops/sugarcane/harvesting_and_processing/sugarcane-ripener-recommendations--glyphosate |website=]|publisher=Louisiana State University, College of Agriculture |archive-url=https://web.archive.org/web/20180920175015/https://www.lsuagcenter.com/topics/crops/sugarcane/harvesting_and_processing/sugarcane-ripener-recommendations--glyphosate |archive-date=20 September 2018 |date=14 August 2017}}</ref> In grain crops (wheat, barley, oats), uniformly dried crops do not have to be ]ed (swathed and dried) prior to harvest, but can easily be straight-cut and harvested. This saves the farmer time and money, which is important in northern regions where the growing season is short, and it enhances grain storage when the grain has a lower and more uniform moisture content.<ref name=moneuro/><ref>{{cite web |title=Pre-harvest Management of Small Grains |url=https://blog-crop-news.extension.umn.edu/2017/07/pre-harvest-management-of-small-grains.html |website=Minnesota Crop News |publisher=]|archive-url=https://web.archive.org/web/20190527142012/https://blog-crop-news.extension.umn.edu/2017/07/pre-harvest-management-of-small-grains.html |archive-date=27 May 2019 |language=en |date=18 July 2017}}</ref><ref>{{cite web |last1=Fowler |first1=D.B. |title=Harvesting, Grain Drying and Storage – Chapter 23 |url=https://www.usask.ca/agriculture/plantsci/winter_cereals/winter-wheat-production-manual/chapter-23.php |website=Winter Wheat Production Manual |publisher=]|archive-url=https://web.archive.org/web/20181209105427/https://www.usask.ca/agriculture/plantsci/winter_cereals/winter-wheat-production-manual/chapter-23.php |archive-date=9 December 2018|language=en|access-date=2017-05-03}}</ref>

===Genetically modified crops===
{{Main|Genetically modified crops|Genetically modified organism|Genetically modified food|Genetically modified food controversies}}
Some micro-organisms have a version of ] (EPSPS) resistant to glyphosate inhibition. A version of the enzyme that was both resistant to glyphosate and that was still efficient enough to drive adequate plant growth was identified by Monsanto scientists after much trial and error in an '']'' strain called CP4, which was found surviving in a waste-fed column at a glyphosate production facility.<ref name="Pollegioni_2011"/><ref name="Green_2011">{{cite journal | vauthors = Green JM, Owen MD | title = Herbicide-resistant crops: utilities and limitations for herbicide-resistant weed management | journal =]| volume = 59 | issue = 11 | pages = 5819–29 | date = Jun 2011 | pmid = 20586458 | pmc = 3105486 | doi = 10.1021/jf101286h }}</ref><ref>{{cite book | vauthors = Rashid A | title = Introduction to Genetic Engineering of Crop Plants: Aims and Achievements | year = 2009 | publisher = I K International | isbn = 978-93-80026-16-9 | pages = 259 }}</ref>{{rp|56}} This ''CP4'' EPSPS gene was ] and ] into soybeans. In 1996, genetically modified soybeans were made commercially available.<ref name="urlMonsanto | Company History">{{cite web | url = https://monsanto.com/company/history/ | title = Company History | work = Web Site | publisher = Monsanto Company | access-date = June 27, 2017 | archive-date = November 5, 2018 | archive-url = https://web.archive.org/web/20181105125639/https://monsanto.com/company/history/ | url-status = dead }}</ref> Current glyphosate-resistant crops include soy, ] (corn), ], ], ], and ], with ] still under development.

In 2023, 91% of corn, 95% of soybeans, and 94% of cotton produced in the United States were from strains that were genetically modified to be tolerant to multiple herbicides, including ], ], and glyphosate.<ref name=USDA1>{{cite web|title=Adoption of Genetically Engineered Crops in the U.S.|url=http://www.ers.usda.gov/data-products/adoption-of-genetically-engineered-crops-in-the-us/recent-trends-in-ge-adoption.aspx|website=]|publisher=USDA|access-date =26 March 2024}}</ref>

==Environmental fate==
] company in ] applying a weed control product that contains glyphosate]]
Glyphosate has four ionizable sites, with ] values of 2.0, 2.6, 5.6 and 10.6.<ref>P. Sprankle, W. F. Meggitt, D. Penner: ''Adsorption, mobility, and microbial degradation of glyphosate in the soil''. In: ''Weed Sci.'' 23(3), p.&nbsp;229–234, as cited in .</ref> Therefore, it is a zwitterion in aqueous solutions and is expected to exist almost entirely in zwitterionic forms in the environment. Zwitterions generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts.<ref>{{cite web |title = PubChem Compound Summary for CID 3496, Glyphosate | publisher = National Center for Biotechnology Information | access-date = June 16, 2022 | url = https://pubchem.ncbi.nlm.nih.gov/compound/Glyphosate}}</ref> Glyphosate strongly ] onto ] minerals, and, with the exception of ], its soluble residues are expected to be poorly mobile in the free porewater of soils. The spatial extent of ] and ] pollution is therefore considered to be relatively limited.<ref name = "Borggaard_2008" /> Glyphosate is readily degraded by soil microbes to ] (AMPA, which like glyphosate strongly adsorbs to soil solids and is thus unlikely to leach to groundwater). Though both glyphosate and AMPA are commonly detected in water bodies, a portion of the AMPA detected may actually be the result of degradation of detergents and other ]s rather than degradation of glyphosate.<ref>{{cite journal | vauthors = Botta F, Lavisonb G, Couturier G, Alliot F, Moreau-Guigon E, Fauchon N, Guery B, Chevreuil M, Blanchoud H | year = 2009 | title = Transfer of glyphosate and its degradate AMPA to surface waters through urban sewerage systems | journal = Chemosphere | volume = 77 | issue = 1| pages = 133–139 | doi=10.1016/j.chemosphere.2009.05.008 | pmid=19482331| bibcode = 2009Chmsp..77..133B}}</ref> The proportion of AMPA from non-glyphosate sources is claimed to be higher in Europe compared to USA.<ref name="u859">{{cite journal | last=Schwientek | first=M. | last2=Rügner | first2=H. | last3=Haderlein | first3=S.B. | last4=Schulz | first4=W. | last5=Wimmer | first5=B. | last6=Engelbart | first6=L. | last7=Bieger | first7=S. | last8=Huhn | first8=C. | title=Glyphosate contamination in European rivers not from herbicide application? | journal=Water Research | volume=263 | date=2024 | doi=10.1016/j.watres.2024.122140 | page=122140}}</ref> Glyphosate does have the potential to contaminate surface waters due to its aquatic use patterns and through erosion, as it adsorbs to ]al soil particles suspended in ]. Detection in surface waters (particularly downstream from agricultural uses) has been reported as both broad and frequent by the ] (USGS) researchers,<ref>{{cite journal |last1=Battaglin |first1=W.A. |last2=Meyer |first2=M.T. |last3=Kuivila |first3=K.M. |last4=Dietze |first4=J.E. |title=Glyphosate and Its Degradation Product AMPA Occur Frequently and Widely in U.S. Soils, Surface Water, Groundwater, and Precipitation |journal=JAWRA Journal of the American Water Resources Association |date=April 2014 |volume=50 |issue=2 |pages=275–90 |doi=10.1111/jawr.12159|bibcode=2014JAWRA..50..275B |s2cid=15865832 }}</ref> although other similar research found equal frequencies of detection in urban-dominated small streams.<ref>{{cite journal |last1=Mahler |first1=Barbara J. |last2=Van Metre |first2=Peter C. |last3=Burley |first3=Thomas E. |last4=Loftin |first4=Keith A. |last5=Meyer |first5=Michael T. |last6=Nowell |first6=Lisa H. |title=Similarities and differences in occurrence and temporal fluctuations in glyphosate and atrazine in small Midwestern streams (USA) during the 2013 growing season |journal=Science of the Total Environment |date=February 2017 |volume=579 |pages=149–58 |doi=10.1016/j.scitotenv.2016.10.236|pmid=27863869 |bibcode=2017ScTEn.579..149M |doi-access=free }}</ref> Rain events can trigger dissolved glyphosate loss in transport-prone soils.<ref>{{cite journal |last1=Richards |first1=Brian K. |last2=Pacenka |first2=Steven |last3=Meyer |first3=Michael T. |last4=Dietze |first4=Julie E. |last5=Schatz |first5=Anna L. |last6=Teuffer |first6=Karin |last7=Aristilde |first7=Ludmilla |last8=Steenhuis |first8=Tammo S. |title=Antecedent and Post-Application Rain Events Trigger Glyphosate Transport from Runoff-Prone Soils |journal=Environmental Science & Technology Letters |date=23 April 2018 |volume=5 |issue=5 |pages=249–54 |doi=10.1021/acs.estlett.8b00085|bibcode=2018EnSTL...5..249R }}</ref> The mechanism of glyphosate sorption to soil is similar to that of ] fertilizers, the presence of which can reduce glyphosate sorption.<ref>{{cite journal | vauthors = Muniraa S, Farenhorsta A, Flatena D, Grant C | year = 2016 | title = Phosphate fertilizer impacts on glyphosate sorption by soil | journal = Chemosphere | volume = 153 | pages = 471–77 | doi=10.1016/j.chemosphere.2016.03.028| pmid = 27035384 | bibcode = 2016Chmsp.153..471M| hdl = 1993/31877 | hdl-access = free }}</ref> Phosphate fertilizers are subject to release from sediments into water bodies under ] conditions, and similar release can also occur with glyphosate, though significant impact of glyphosate release from sediments has not been established.<ref>{{cite journal | vauthors = Kanissery RG, Welsh A, Sims GK | s2cid = 31227173 | year = 2014 | title = Effect of soil aeration and phosphate addition on the microbial bioavailability of 14C-glyphosate | journal = Journal of Environmental Quality| volume = 44 | issue = 1| pages = 137–44 | doi = 10.2134/jeq2014.08.0331 | pmid = 25602328 }}</ref> Limited leaching can occur after high rainfall after application. If glyphosate reaches surface water, it is not broken down readily by water or sunlight.<ref name="epa_reds"/><ref name = "Borggaard_2008">{{cite journal | vauthors = Borggaard OK, Gimsing AL | title = Fate of glyphosate in soil and the possibility of leaching to ground and surface waters: a review | journal = Pest Management Science | volume = 64 | issue = 4 | pages = 441–56 | date = Apr 2008 | doi = 10.1002/ps.1512 | pmid = 18161065 | doi-access = free }}</ref>

The ] of glyphosate in soil ranges between 2 and 197 days; a typical field half-life of 47 days has been suggested. Soil and climate conditions affect glyphosate's persistence in soil. The median half-life of glyphosate in water varies from a few to 91 days.<ref name="NPIC Data Sheet"/> At a site in Texas, half-life was as little as three days. A site in Iowa had a half-life of 141.9 days.<ref name=Giesy2000 /> The glyphosate metabolite AMPA has been found in Swedish forest soils up to two years after a glyphosate application. In this case, the persistence of AMPA was attributed to the soil being frozen for most of the year.<ref name="pmid2806176">{{cite journal | vauthors = Torstensson NT, Lundgren LN, Stenström J | title = Influence of climatic and edaphic factors on persistence of glyphosate and 2,4-D in forest soils | journal = Ecotoxicology and Environmental Safety | volume = 18 | issue = 2 | pages = 230–39 | date = Oct 1989 | pmid = 2806176 | doi = 10.1016/0147-6513(89)90084-5 | bibcode = 1989EcoES..18..230T }}</ref> Glyphosate adsorption to soil, and later release from soil, varies depending on the kind of soil.<ref name="pmid19447533">{{cite journal | vauthors = Albers CN, Banta GT, Hansen PE, Jacobsen OS | title = The influence of organic matter on sorption and fate of glyphosate in soil--comparing soils and humic substances | journal = Environmental Pollution | volume = 157 | issue = 10 | pages = 2865–70 | date = Oct 2009 | pmid = 19447533 | doi = 10.1016/j.envpol.2009.04.004 | bibcode = 2009EPoll.157.2865A }}</ref><ref>{{cite journal | url = http://www.academyjournal.net/asj/index.php/TSPN/article/viewArticle/193 | title = Does phosphate affect soil sorption and degradation of glyphosate? – A review | vauthors = Ole K, Borggaard OK | journal = Trends in Soil Science and Plant Nutrition | volume = 2 | issue = 1 | year = 2011 | pages = 17–27 }}{{Dead link|date=December 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> Glyphosate is generally less persistent in water than in soil, with 12- to 60-day persistence observed in Canadian ponds, although persistence of over a year has been recorded in the sediments of American ponds.<ref name="epa_reds"/> The half-life of glyphosate in water is between 12 days and 10 weeks.<ref name="Sparling">{{cite journal | vauthors = Sparling DW, Matson C, Bickham J, Doelling-Brown P | year = 2006 | title = Toxicity of glyphosate as Glypro® and LI700 to red-eared slider (''Trachemys scripta elegans'') embryos and early hatchlings | journal = Environmental Toxicology and Chemistry | volume = 25 | issue = 10 | pages = 2768–74 | doi = 10.1897/05-152.1 | pmid = 17022419 | s2cid = 12954689 }}</ref>

===Residues in food products===
According to the ] fact sheet, glyphosate is not included in compounds tested for by the Food and Drug Administration's Pesticide Residue Monitoring Program, nor in the United States Department of Agriculture's Pesticide Data Program.<ref name="NPIC Data Sheet"/> The U.S. has determined the ] of glyphosate at 1.75 milligrams per kilogram of body weight per day (mg/kg/bw/day) while the European Union has set it at 0.5.<ref>{{cite web | last = European Commission| date = 2017 | url = http://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/public/?event=activesubstance.detail&language=EN&selectedID=1438 | title = EU Pesticides database: Glyphosate| access-date = 29 August 2018}}</ref>

Pesticide residue controls carried out by EU Member States in 2016 analysed 6,761 samples of food products for glyphosate residues. 3.6% of the samples contained ] glyphosate residue levels with 19 samples (0.28%) exceeding the European ] (MRLs), which included six samples of honey and other apicultural products (MRL = 0.05&nbsp;mg/kg) and eleven samples of buckwheat and other pseudo‐cereals (MRL = 0.1&nbsp;mg/kg). Glyphosate residues below the European MRLs were most frequently found in dry lentils, linseeds, soya beans, dry peas, tea, buckwheat, barley, wheat and rye.<ref name="ESFA2018residues">{{cite journal |last1=European Food Safety Authority |title=The 2016 European Union report on pesticide residues in food |journal= EFSA Journal|date=July 2018 |volume=16 |issue=7 |page=67 |doi=10.2903/j.efsa.2018.5348 |pmid=32625983 |pmc=7009629 |doi-access=free }}</ref> In Canada, a survey of 7,955 samples of food found that 42.3% contained detectable quantities of glyphosate and only 0.6% contained a level higher than the Canadian MRL of 0.1&nbsp;mg/kg for most foods and 4&nbsp;mg/kg for beans and chickpeas. Of the products that exceeded MRLs, one third were organic products. ] concluded based on the analysis "that there was no long-term health risk to Canadian consumers from exposure to the levels of glyphosate".<ref>{{cite journal |last1=Kolakowski |first1=Beata M. |last2=Miller |first2=Leigh |last3=Murray |first3=Angela |last4=Leclair |first4=Andrea |last5=Bietlot |first5=Henri |last6=van de Riet |first6=Jeffrey M. |title=Analysis of Glyphosate Residues in Foods from the Canadian Retail Markets between 2015 and 2017 |journal=Journal of Agricultural and Food Chemistry |date=6 May 2020 |volume=68 |issue=18 |pages=5201–5211 |doi=10.1021/acs.jafc.9b07819|pmid=32267686 |doi-access=free }}</ref>

==Toxicity==
Glyphosate is the active ingredient in herbicide formulations containing it. However, in addition to glyphosate salts, commercial formulations of glyphosate contain additives (known as adjuvants) such as ]s, which vary in nature and concentration. Surfactants such as ] (POEA) are added to glyphosate to enable it to wet the leaves and penetrate the ] of the plants.

===Glyphosate alone===
====Humans====
The acute oral toxicity for mammals is low,<ref name="pmid29117584">{{cite journal | vauthors = Van Bruggen AC, He MM, Shin K, Mai V, Jeong KC, Finckh MR, Morris JG | title = Environmental and health effects of the herbicide glyphosate | journal = Sci. Total Environ. | volume = 616–17 | pages = 255–68 | date = March 2018 | pmid = 29117584 | doi = 10.1016/j.scitotenv.2017.10.309 | bibcode = 2018ScTEn.616..255V }}</ref> but death has been reported after deliberate overdose of ] formulations.<ref name="pmid22835958">{{cite journal |vauthors= Sribanditmongkol P, Jutavijittum P, Pongraveevongsa P, Wunnapuk K, Durongkadech P |title= Pathological and toxicological findings in glyphosate-surfactant herbicide fatality: a case report |journal= The American Journal of Forensic Medicine and Pathology |volume= 33 |issue=3 |pages= 234–37 |date= Sep 2012 |doi= 10.1097/PAF.0b013e31824b936c |pmid= 22835958 |s2cid= 3457850 }}</ref> The surfactants in glyphosate formulations can increase the relative acute toxicity of the formulation.<ref name="Bradberry_2004">{{cite journal |vauthors= Bradberry SM, Proudfoot AT, Vale JA |s2cid= 5636017 |title= Glyphosate poisoning |journal = Toxicological Reviews |volume= 23 |issue=3 |pages= 159–67 |year= 2004 |pmid= 15862083 |doi= 10.2165/00139709-200423030-00003}}</ref><ref name=SERA2003>{{Citation| title = Glyphosate: Human Health and Ecological Risk Assessment | publisher= Syracuse Environmental Research Associates, Inc.(SERA) |access-date = 2018-08-20| url = https://www.fs.fed.us/r5/hfqlg/publications/herbicide_info/2003_glyphosate.pdf}}</ref> Glyphosate is less toxic than 94% of herbicides, and is also less toxic than household chemicals such as ] or ].<ref name="PennStateExt">{{cite web |last1=Wallace |first1=John |last2=Lingenfelter |first2=Dwight |title=Glyphosate (Roundup): Understanding Risks to Human Health |url=https://extension.psu.edu/glyphosate-roundup-understanding-risks-to-human-health |website=extension.psu.edu |publisher=Pennsylvania State University Extension |access-date=12 July 2024 |language=en}}</ref>

In a 2017 risk assessment, the European Chemicals Agency (ECHA) wrote: "There is very limited information on skin irritation in humans. Where skin irritation has been reported, it is unclear whether it is related to glyphosate or co-formulants in glyphosate-containing herbicide formulations." The ECHA concluded that available human data was insufficient to support classification for skin corrosion or irritation.<ref>{{Cite web|url=https://echa.europa.eu/documents/10162/2f8b5c7f-030f-5d3a-e87e-0262fb392f38|title=Committee of Risk Assessment Opinion proposing harmonised classification and labelling at EU level of glyphosate (ISO); N-(phosphonomethyl)glycine}}</ref> 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.<ref name="Bradberry_2004"/>

====Cancer====
The ] among national pesticide regulatory agencies and scientific organizations is that labeled uses of glyphosate have demonstrated no evidence of human carcinogenicity.<ref name=Tarazona/> The Joint FAO/WHO Meeting on Pesticide Residues (JMPR),<ref name="JMPR2016">{{cite book |last1=Boobis |first1=Alan R. |title=Pesticide residues in food 2016, Joint FAO/WHO Meeting on Pesticide Residues, 9–13 May 2016 |date=2016 |publisher=WHO/FAO |location=Rome |isbn=978-92-5-109246-0 |pages=19–28 |url=https://www.who.int/foodsafety/areas_work/chemical-risks/JMPR_2016_Report_May.pdf}}</ref> the ], the Canadian ], the ]<ref>{{Cite book| publisher = SAGE Publications, Inc.| isbn = 978-1-4129-6987-1| last1 = Guston| first1 = David| last2 = Ludlow| first2 = Karinne| title = Encyclopedia of Nanoscience and Society| chapter = Australian Pesticides and Veterinary Medicines Authority| location = Thousand Oaks, CA| date = 2010| chapter-url = http://sk.sagepub.com/reference/nanoscience/n22.xml}}</ref> and the German ]<ref>{{Cite web| title = The BfR has finalised its draft report for the re-evaluation of glyphosate – BfR| access-date = 2018-08-18| url = https://www.bfr.bund.de/en/the_bfr_has_finalised_its_draft_report_for_the_re_evaluation_of_glyphosate-188632.html}}</ref> have concluded that there is no evidence that glyphosate poses a carcinogenic or ] risk to humans. The ] (EPA) has classified glyphosate as "not likely to be carcinogenic to humans."<ref>{{Cite web| last = US EPA| first = OCSPP| title = EPA Releases Draft Risk Assessments for Glyphosate| work = US EPA| format = Announcements and Schedules| access-date = 2018-08-18| date = 2017-12-18| url = https://www.epa.gov/pesticides/epa-releases-draft-risk-assessments-glyphosate}}</ref><ref name="CARC2015">{{cite book |last1=Cancer Assessment Review Committee, HED, Office of Pesticides Program, US EPA |title=Evaluation of the Carcinogenic potential of Glyphosate, Final Report |date=October 1, 2015 |publisher=US EPA |location=Washington |pages=77–78 |url=http://src.bna.com/eAi}}</ref> One international scientific organization, the ], classified glyphosate in ], "probably carcinogenic to humans" in 2015.<ref name="iarcmono"/><ref name="Lancet20March2015"/>

{{As of|2020}}, the evidence for long-term exposure to glyphosate increasing the risk of human cancer remains inconclusive.<ref>{{cite journal|vauthors = Agostini LP, Dettogni RS, Dos Reis RS, Stur E, Dos Santos E, Ventorim DP, Garcia FM, Cardoso RC, Graceli JB, Louro ID|title= Effects of glyphosate exposure on human health: Insights from epidemiological and in vitro studies|url=https://pubmed.ncbi.nlm.nih.gov/31972943/|journal=Sci Total Environ|volume=705|page=135808|date=2020|doi= 10.1016/j.scitotenv.2019.135808|pmid= 31972943|bibcode= 2020ScTEn.70535808A|s2cid= 210883035}}</ref> There is weak evidence human cancer risk might increase as a result of occupational exposure to large amounts of glyphosate, such as in agricultural work, but no good evidence of such a risk from home use, such as in domestic gardening.<ref name=cruk>{{cite web |publisher=Cancer Research UK| title=Food Controversies&nbsp;– Pesticides and organic foods|url=http://www.cancerresearchuk.org/about-cancer/causes-of-cancer/diet-and-cancer/food-controversies#food_controversies4 |date=2016 |access-date=28 November 2017}}</ref><ref>{{cite journal|vauthors=Donato F, Pira E, Ciocan C, Boffetta P|title=Exposure to glyphosate and risk of non-Hodgkin lymphoma and multiple myeloma: an updated meta-analysis|journal=Med Lav|volume=111|pages=63–73|date=2020|issue=1|pmid=32096774|pmc=7809965}}</ref>

Although some small studies have suggested an association between glyphosate and ], subsequent work confirmed the likelihood this work suffered from bias, and the association could not be demonstrated in more robust studies.<ref name=boff>{{cite journal |vauthors=Boffetta P, Ciocan C, Zunarelli C, Pira E |title=Exposure to glyphosate and risk of non-Hodgkin lymphoma: an updated meta-analysis |journal=Med Lav |volume=112 |issue=3 |pages=194–199 |date=June 2021 |pmid=34142676 |pmc=8223940 |doi=10.23749/mdl.v112i3.11123 |type=Meta-analysis}}</ref><ref name="EFSA2023">{{cite journal |vauthors=Álvarez F, Arena M, Auteri D, Binaglia M, Castoldi AF, Chiusolo A, Crivellente F, Egsmose M, Fait G, Ferilli F, Gouliarmou V, Nogareda LH, Ippolito A, Istace F, Jarrah S, Kardassi D, Kienzler A, Lanzoni A, Lava R, Linguadoca A, Lythgo C, Mangas I, Padovani L, Panzarea M, Parra Morte JM, Rizzuto S, Romac A, Rortais A, Serafimova R, Sharp R, Szentes C, Terron A, Theobald A, Tiramani M, Vianello G, Villamar-Bouza L |title=Peer review of the pesticide risk assessment of the active substance glyphosate |journal=EFSA J |volume=21 |issue=7 |pages=e08164 |date=July 2023 |pmid=37502013 |pmc=10369247 |doi=10.2903/j.efsa.2023.8164 |type=Review |display-authors=5}}</ref><ref>{{Cite web |date=2023-08-25 |orig-date= |title=Peer Review Report on Glyphosate (AIR V) Part 3 of 6: Report of Pesticide Peer Review TC 80 |url=https://open.efsa.europa.eu/study-inventory/EFSA-Q-2020-00140 |archive-format= |access-date=2023-11-16 |pages=59–78 |language=en |publication-place=EFSA|quote= The available epidemiological studies currently do not provide sufficient indication that glyphosate exposure is associated with any cancer-related health effect.}}</ref>

====Other mammals====
Amongst mammals, glyphosate is considered to have "low to very low toxicity". The ] of glyphosate is 5,000&nbsp;mg/kg for rats, 10,000&nbsp;mg/kg in mice and 3,530&nbsp;mg/kg in goats. The acute dermal LD<sub>50</sub> in rabbits is greater than 2,000&nbsp;mg/kg. Indications of glyphosate toxicity in animals typically appear within 30 to 120 minutes following ingestion of a large enough dose, and include initial excitability and ], ], depression, and ], although severe toxicity can develop into collapse and convulsions.<ref name="NPIC Data Sheet"/>

A review of unpublished short-term rabbit-feeding studies reported severe toxicity effects at 150&nbsp;mg/kg/day and "]" doses ranging from 50 to 200&nbsp;mg/kg/day.<ref name="pmid23286529">{{cite journal | vauthors = Kimmel GL, Kimmel CA, Williams AL, DeSesso JM | title = Evaluation of developmental toxicity studies of glyphosate with attention to cardiovascular development | journal = Critical Reviews in Toxicology | volume = 43 | issue = 2 | pages = 79–95 | year = 2013 | pmid = 23286529 | pmc = 3581053 | doi = 10.3109/10408444.2012.749834 }}</ref> Glyphosate can have carcinogenic effects in nonhuman mammals. These include the induction of positive trends in the incidence of ] and ] in male mice, and increased ] in male rats.<ref name="Lancet20March2015" /> In reproductive toxicity studies performed in rats and rabbits, no adverse maternal or offspring effects were seen at doses below 175–293&nbsp;mg/kg/day.<ref name="NPIC Data Sheet"/>

Large quantities of glyphosate-based herbicides may cause life-threatening ]s in mammals. Evidence also shows that such herbicides cause direct electrophysiological changes in the cardiovascular systems of rats and rabbits.<ref>{{cite journal | vauthors = Gress S, Lemoine S, Séralini GE, Puddu PE | s2cid = 17936407 | title = Glyphosate-based herbicides potently affect cardiovascular system in mammals: review of the literature | journal = Cardiovascular Toxicology | volume = 15 | issue = 2 | pages = 117–26 | date = April 2015 | pmid = 25245870 | doi = 10.1007/s12012-014-9282-y }}</ref>

====Aquatic fauna====
In many freshwater invertebrates, glyphosate has a 48-hour ] ranging from 55 to 780 ppm. The 96-hour LC<sub>50</sub> is 281 ppm for ] (''Palaemonetas vulgaris'') and 934 ppm for ] (''Uca pagilator''). These values make glyphosate "slightly toxic to practically non-toxic".<ref name="NPIC Data Sheet"/>

====Antimicrobial activity====
The ] activity of glyphosate has been described in the microbiology literature since its discovery in 1970 and the description of glyphosate's mechanism of action in 1972. Efficacy was described for numerous bacteria and fungi.<ref>Abraham William Wildwood. , US Patent 7, 771, 736 B2; 2010</ref> Glyphosate can control the growth of ]n parasites, such as '']'', '']'' (malaria), and '']'', and has been considered an antimicrobial agent in mammals.<ref name="pmid11865437">{{cite journal | vauthors = Roberts CW, Roberts F, Lyons RE, Kirisits MJ, Mui EJ, Finnerty J, Johnson JJ, Ferguson DJ, Coggins JR, Krell T, Coombs GH, Milhous WK, Kyle DE, Tzipori S, Barnwell J, Dame JB, Carlton J, McLeod R | title = The shikimate pathway and its branches in apicomplexan parasites | journal = The Journal of Infectious Diseases | volume = 185 | issue = Suppl 1 | pages = S25–36 | date = Feb 2002 | pmid = 11865437 | doi = 10.1086/338004 | doi-access = free }}</ref> Inhibition can occur with some ] species important for soybean nitrogen fixation, especially under moisture stress.<ref name="pmid15224916">{{cite journal | vauthors = Zablotowicz RM, Reddy KN | title = Impact of glyphosate on the Bradyrhizobium japonicum symbiosis with glyphosate-resistant transgenic soybean: a minireview | journal = Journal of Environmental Quality | volume = 33 | issue = 3 | pages = 825–31 | year = 2004 | pmid = 15224916 | doi = 10.2134/jeq2004.0825 | bibcode = 2004JEnvQ..33..825Z }}</ref>

====Soil biota====
]
When glyphosate comes into contact with the soil, it can be bound to ], thereby slowing its degradation.<ref name="epa_reds"/><ref name=Andrea>{{cite journal | title = Influence of repeated applications of glyphosate on its persistence and soil bioactivity | year = 2003 | vauthors = Andréa MM, Peres TB, Luchini LC, Bazarin S, Papini S, Matallo MB, Savoy VL | journal = Pesquisa Agropecuária Brasileira | volume = 38 | issue = 11 | pages = 1329–35 | doi = 10.1590/S0100-204X2003001100012 | doi-access = free }}</ref> Glyphosate and its degradation product, ] are considered to be much more benign toxicologically and environmentally than most of the herbicides replaced by glyphosate.<ref>{{cite journal | vauthors = Cerdeira AL, Duke SO | title = Effects of glyphosate-resistant crop cultivation on soil and water quality | journal = GM Crops | volume = 1 | issue = 1 | pages = 16–24 | date = January 2010 | pmid = 21912208 | doi = 10.4161/gmcr.1.1.9404 | s2cid = 38119904 | url = http://ainfo.cnptia.embrapa.br/digital/bitstream/item/47350/1/2010AP03-2.pdf }}</ref> A 2016 meta-analysis concluded that at typical application rates glyphosate had no effect on soil microbial biomass or respiration.<ref name="NguyenRose2016">{{cite journal | last1 = Nguyen | first1 = Duy B. | last2 = Rose | first2 = Michael T. | last3 = Rose | first3 = Terry J. | last4 = Morris | first4 = Stephen G. | last5 = van Zwieten | first5 = Lukas | name-list-style = vanc | title = Impact of glyphosate on soil microbial biomass and respiration: A meta-analysis | journal = Soil Biology and Biochemistry | volume = 92 | year = 2016| pages = 50–57 | issn = 0038-0717 | doi = 10.1016/j.soilbio.2015.09.014 | bibcode = 2016SBiBi..92...50N }}</ref> Some species of earthworms are affected, some are not. Some avoid treated soil.<ref name="RoseCavagnaro2016">{{cite book |last1=Rose|first1=Michael T. |last2=Cavagnaro |first2=Timothy R. |last3=Scanlan |first3=Craig A. |last4=Rose |first4=Terry J.|last5=Vancov |first5=Tony |last6=Kimber |first6=Stephen |last7=Kennedy |first7=Ivan R. |last8=Kookana |first8=Rai S. |last9=Van Zwieten |first9=Lukas |series=Advances in Agronomy | name-list-style = vanc |title=Impact of Herbicides on Soil Biology and Function |volume=136 |year=2016 |pages=168 |doi=10.1016/bs.agron.2015.11.005 |hdl=2440/110451 |isbn=978-0128046814}}</ref>

====Endocrine disruption====
In 2007, the EPA selected glyphosate for further screening through its Endocrine Disruptor Screening Program (EDSP). Selection for this program is based on a compound's prevalence of use and does not imply particular suspicion of ] activity.<ref>{{cite journal | author = United States Environmental Protection Agency | journal = Federal Register | volume = 72 | issue = 116 | pages = 33486–503 | date = 18 June 2007 | title = Draft List of Initial Pesticide Active Ingredients and Pesticide Inerts to be Considered for Screening under the Federal Food, Drug, and Cosmetic Act | url = http://www.epa.gov/endo/pubs/draft_list_frn_061807.pdf }}</ref> On June 29, 2015, the EPA released the Weight of Evidence Conclusions of the EDSP Tier 1 screening for glyphosate, recommending that glyphosate not be considered for Tier 2 testing. The Weight of Evidence conclusion stated "...there was no convincing evidence of potential interaction with the ], ] or ] pathways."<ref>{{cite web |author= United States Environmental Protection Agency |title= Memorandum: EDSP Weight of Evidence Conclusions on the Tier 1 Screening Assays for the List 1 Chemicals |url= http://www2.epa.gov/sites/production/files/2015-06/documents/glyphosate-417300_2015-06-29_txr0057175.pdf |archive-url= https://web.archive.org/web/20160116111524/http://www.epa.gov/sites/production/files/2015-06/documents/glyphosate-417300_2015-06-29_txr0057175.pdf |archive-date= 16 January 2016 |date= 29 June 2015 }}</ref> A review of the evidence by the European Food Safety Authority published in September 2017 showed conclusions similar to those of the EPA report.<ref>{{cite journal |title=Peer review of the pesticide risk assessment of the potential endocrine disrupting properties of glyphosate |journal= EFSA Journal|date=September 2017 |volume=15 |issue=9 |doi=10.2903/j.efsa.2017.4979|pmid= 32625644|doi-access=free |author1= European Food Safety Authority |pages= e04979|pmc= 7010201}}</ref>

====Effect on plant health====
Some studies have found causal relationships between glyphosate and increased or decreased disease resistance.<ref>{{cite book |doi=10.1007/978-1-4020-5799-1_15 |chapter=Interactions of Synthetic Herbicides with Plant Disease and Microbial Herbicides |title=Novel Biotechnologies for Biocontrol Agent Enhancement and Management |series=NATO Security through Science Series |year=2007 | vauthors = Duke SO, Wedge DE, Cerdeira AL, Matallo MB | isbn = 978-1-4020-5797-7 | pages = 277–96 |publisher=Springer |location=Dordrecht | editor1-first = Maurizio | editor1-last = Vurro | editor2-first = Jonathan | editor2-last = Gressel }}</ref> Exposure to glyphosate has been shown to change the species composition of ] in plant hosts, which is highly variable.<ref>{{cite journal | vauthors = Rosenblueth M, Martínez-Romero E | title = Bacterial endophytes and their interactions with hosts | journal = Molecular Plant-Microbe Interactions | volume = 19 | issue = 8 | pages = 827–37 | date = Aug 2006 | pmid = 16903349 | doi = 10.1094/MPMI-19-0827 | doi-access = free }}</ref>

===Glyphosate-based formulations===
Glyphosate-based formulations may contain a number of ], the identities of which may be proprietary.<ref name="www2.epa.gov">{{cite web |url=http://www2.epa.gov/pesticide-registration/pesticide-registration-manual |title=Pesticide Registration Manual &#124; Pesticide Registration &#124; US EPA |date=March 4, 2013 |access-date=March 7, 2014 |archive-date=April 14, 2016 |archive-url=https://web.archive.org/web/20160414065403/https://www.epa.gov/pesticide-registration/pesticide-registration-manual |url-status=dead }}</ref> Surfactants are used in herbicide formulations as ] agents, to maximize coverage and aid penetration of the herbicide(s) through plant leaves. As agricultural spray adjuvants, surfactants may be pre-mixed into commercial formulations or they may be purchased separately and mixed on-site.<ref>{{cite web |title=Adjuvants for Enhancing Herbicide Performance |url=https://extension.psu.edu/adjuvants-for-enhancing-herbicide-performance |website=extension.psu.edu |publisher=Penn State Extension |access-date=15 August 2018 |language=en}}</ref>

] (POEA) is a surfactant used in the original Roundup formulation and was commonly used in 2015.<ref name=usgs.glyphosate.poea>{{cite web|title=Measuring POEA, a Surfactant Mixture in Herbicide Formulations|url=http://toxics.usgs.gov/highlights/glyphosate_poea.html|publisher=U.S. Geological Survey|access-date=May 29, 2015|archive-date=October 7, 2015|archive-url=https://web.archive.org/web/20151007051906/http://toxics.usgs.gov/highlights/glyphosate_poea.html|url-status=dead}}</ref> The percentage of POEA varies. A 1997 US government report said that Roundup is 15% POEA while Roundup Pro is 14.5%.<ref name="fs.fed.us"/> Since POEA is more toxic to fish and amphibians than glyphosate alone, POEA is not allowed in aquatic formulations.<ref name="Langeland"/><ref name="fs.fed.us">Gary L. Diamond and Patrick R. Durkin February 6, 1997, under contract from the United States Department of Agriculture. </ref><ref name=Mann/> As of 2000, at least 58 studies existed on the effects of Roundup on a range of organisms.<ref name=Giesy2000>{{cite book |doi=10.1007/978-1-4612-1156-3_2 |year=2000 | vauthors = Giesy JP, Dobson S, Solomon KR |chapter=Ecotoxicological Risk Assessment for Roundup® Herbicide | isbn = 978-0-387-95102-7 | volume = 167 | pages = 35–120 | chapter-url = https://books.google.com/books?id=7iTdm5ii4NYC&pg=PA35|title=Reviews of Environmental Contamination and Toxicology |publisher=Springer |location=New York, NY }}</ref> This review concluded that "...for terrestrial uses of Roundup minimal acute and chronic risk was predicted for potentially exposed non-target organisms".<ref>{{cite web |title=Ecotoxicological Risk Assessment for Roundup Herbicide |url=https://www.usask.ca/toxicology/jgiesy/pdf/publications/JA-228.pdf |access-date=May 9, 2019 |archive-date=August 7, 2019 |archive-url=https://web.archive.org/web/20190807140955/https://www.usask.ca/toxicology/jgiesy/pdf/publications/JA-228.pdf |url-status=dead }}</ref>

====Human====

Overall, there is no conclusive evidence on glyphosate's effect on human health.<ref>{{cite journal |vauthors=Gillezeau C, van Gerwen M, Shaffer RM, Rana I, Zhang L, Sheppard L, Taioli E |title=The evidence of human exposure to glyphosate: a review |journal=Environ Health |volume=18 |issue=1 |pages=2 |date=January 2019 |pmid=30612564 |pmc=6322310 |doi=10.1186/s12940-018-0435-5 |bibcode=2019EnvHe..18....2G |type=Review |doi-access=free }}</ref><ref>{{cite journal |vauthors=Peillex C, Pelletier M |title=The impact and toxicity of glyphosate and glyphosate-based herbicides on health and immunity |journal=J Immunotoxicol |volume=17 |issue=1 |pages=163–174 |date=December 2020 |pmid=32897110 |doi=10.1080/1547691X.2020.1804492 |s2cid=221541734 |url=|doi-access=free |hdl=20.500.11794/66510 |hdl-access=free }}</ref>

] and ] are dose-related. Skin exposure to ready-to-use concentrated glyphosate formulations can cause irritation, and ] has been occasionally reported. These effects are probably due to the preservative ]. Severe skin burns are very rare.<ref name="Bradberry_2004" /> 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.<ref name="Bradberry_2004" /> Death has been reported after deliberate overdose.<ref name="Bradberry_2004"/><ref name="pmid22835958"/> Ingestion of Roundup ranging from 85 to 200 ml (of 41% solution) 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.<ref name="pmid1673618">{{cite journal | vauthors = Talbot AR, Shiaw MH, Huang JS, Yang SF, Goo TS, Wang SH, Chen CL, Sanford TR | s2cid = 8028945 | title = Acute poisoning with a glyphosate-surfactant herbicide ('Roundup'): a review of 93 cases | journal = Human & Experimental Toxicology | volume = 10 | issue = 1 | pages = 1–8 | date = January 1991 | pmid = 1673618 | doi = 10.1177/096032719101000101 | bibcode = 1991HETox..10....1T }}</ref> Adult consumption of more than 85 ml of concentrated product can lead to corrosive esophageal burns and kidney or liver damage. More severe cases cause "respiratory distress, impaired consciousness, ], ] on chest X-ray, shock, arrhythmias, renal failure requiring haemodialysis, metabolic acidosis, and hyperkalaemia" and death is often preceded by ] and ]s.<ref name="Bradberry_2004" /> While the surfactants in formulations generally do not increase the toxicity of glyphosate itself, it is likely that they contribute to its acute toxicity.<ref name="Bradberry_2004"/>

====Aquatic fauna====
Glyphosate products for aquatic use generally do not use surfactants, and aquatic formulations do not use POEA due to aquatic organism toxicity.<ref name="Langeland">{{cite web |title=SS-AGR-104 Safe Use of Glyphosate-Containing Products in Aquatic and Upland Natural Areas |url=https://edis.ifas.ufl.edu/pdffiles/AG/AG24800.pdf |publisher=University of Florida |access-date=13 August 2018 |archive-date=March 8, 2021 |archive-url=https://web.archive.org/web/20210308112508/https://edis.ifas.ufl.edu/pdffiles/AG/AG24800.pdf |url-status=dead }}</ref> Due to the presence of POEA, such glyphosate formulations only allowed for terrestrial use are more toxic for amphibians and fish than glyphosate alone.<ref name="Langeland"/><ref name="fs.fed.us"/><ref name=Mann>{{cite journal|vauthors=Mann RM, Hyne RV, Choung CB, Wilson SP|title=Amphibians and agricultural chemicals: Review of the risks in a complex environment|journal=Environmental Pollution|year=2009|volume=157|issue=11|pages=2903–27|doi=10.1016/j.envpol.2009.05.015|pmid=19500891|bibcode=2009EPoll.157.2903M |url=http://hdl.cqu.edu.au/10018/35613}}{{Dead link|date=December 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> The half-life of POEA (21–42 days) is longer than that for glyphosate (7–14 days) in aquatic environments.<ref name="Mesnage">{{cite journal | vauthors = Mesnage R, Defarge N, Spiroux de Vendômois J, Séralini GE | title = Potential toxic effects of glyphosate and its commercial formulations below regulatory limits | journal = Food Chem. Toxicol. | volume = 84 | pages = 133–53 | year = 2015 | pmid = 26282372 | doi = 10.1016/j.fct.2015.08.012 | s2cid = 12725778 | author-link4 = Gilles-Éric Séralini | url = https://kclpure.kcl.ac.uk/portal/en/publications/potential-toxic-effects-of-glyphosate-and-its-commercial-formulations-below-regulatory-limits(e185bac2-4db2-4568-b1d2-f258ed2fe7f3).html }}</ref> Aquatic organism exposure risk to terrestrial formulations with POEA is limited to drift or temporary water pockets where concentrations would be much lower than label rates.<ref name="Langeland"/>

Some researchers have suggested the toxicity effects of pesticides on amphibians may differ from those of other aquatic fauna because of their lifestyle; amphibians may be more susceptible to the toxic effects of pesticides because they often prefer to breed in shallow, ], or ephemeral pools. These habitats do not necessarily constitute formal water-bodies and can contain higher concentrations of pesticide compared to larger water-bodies.<ref name="Mann" /><ref name="Govindarajulu">{{cite journal | vauthors= Govindarajulu PP | year = 2008 | title = Literature Review of Impacts of Glyphosate Herbicide on Amphibians: What Risks can the Silvicultural Use of this Herbicide Pose for Amphibians in BC?|publisher=British Columbia, Ecosystems Branch, Ministry of Environment| citeseerx = 10.1.1.314.3577 }}</ref> Studies in a variety of amphibians have shown the toxicity of GBFs containing POEA to amphibian larvae. These effects include interference with gill morphology and mortality from either the loss of osmotic stability or ]. At sub-lethal concentrations, exposure to POEA or glyphosate/POEA formulations have been associated with delayed development, accelerated development, reduced size at ], developmental malformations of the tail, mouth, eye and head, histological indications of intersex and symptoms of oxidative stress.<ref name="Mann" /> Glyphosate-based formulations can cause ] in bullfrog tadpoles.<ref name=iarcmono/>

A 2003 study of various formulations of glyphosate found, " 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."<ref name=Solomon>{{cite journal | vauthors = Solomon KR, Thompson DG | title = Ecological risk assessment for aquatic organisms from over-water uses of glyphosate | journal = Journal of Toxicology and Environmental Health, Part B | volume = 6 | issue = 3 | pages = 289–324 | year = 2003 | pmid = 12746143 | doi = 10.1080/10937400306468 | bibcode = 2003JTEHB...6..289S | s2cid = 42770586 }}</ref>

A 2013 ] reviewed the available data related to potential impacts of glyphosate-based herbicides on amphibians. According to the authors, the use of glyphosate-based pesticides cannot be considered the major cause of amphibian decline, the bulk of which occurred prior to the widespread use of glyphosate or in pristine tropical areas with minimal glyphosate exposure. The authors recommended further study of per-species and per-development-stage chronic toxicity, of environmental glyphosate levels, and ongoing analysis of data relevant to determining what if any role glyphosate might be playing in worldwide amphibian decline, and suggest including amphibians in standardized test batteries.<ref name="ReferenceA">{{cite journal | vauthors = Wagner N, Reichenbecher W, Teichmann H, Tappeser B, Lötters S | title = Questions concerning the potential impact of glyphosate-based herbicides on amphibians | journal = Environmental Toxicology and Chemistry | volume = 32 | issue = 8 | pages = 1688–700 | date = Aug 2013 | pmid = 23637092 | doi = 10.1002/etc.2268 | s2cid = 36417341 }}</ref>

====Genetic damage====
Several studies have not found ],<ref>ToxNet. . National Library of Medicine.</ref> so glyphosate has not been listed in the ] or the ] databases.{{Citation needed|date=December 2019|reason=removed citation to predatory publisher content}} Various other studies suggest glyphosate may be mutagenic.{{Citation needed|date=December 2019|reason=removed citation to predatory publisher content}} The IARC monograph noted that glyphosate-based formulations can cause DNA strand breaks in various ] of animals ''in vitro''.<ref name=iarcmono/>

===Government and organization positions===
====European Food Safety Authority====
A 2013 systematic review by the ] (BfR) examined more than 1000<ref>{{cite web|url=http://www.bfr.bund.de/en/press_information/2014/03/glyphosate__no_more_poisonous_than_previously_assumed__although_a_critical_view_should_be_taken_of_certain_co_formulants-188898.html|title=Glyphosate: no more poisonous than previously assumed, although a critical view should be taken of certain co-formulants – BfR|website=Bfr.bund.de}}</ref> ] studies, animal studies, and '']'' studies. It found that "no classification and labelling for carcinogenicity is warranted" and did not recommend a carcinogen classification of either 1A or 1B.<ref name=BFR2014/>{{rp|34–37, 139}} It provided the review to ] in January 2014 which published it in December 2014.<ref name=BFR2014>Renewal Assessment Report: Glyphosate. Volume 1. Report and Proposed Decision. December 18, 2013. German Institute for Risk Assessment, page 65. Downloaded from http://dar.efsa.europa.eu/dar-web/provision {{Webarchive|url=https://web.archive.org/web/20090130105523/http://dar.efsa.europa.eu/dar-web/provision |date=January 30, 2009 }} (registration required)</ref><ref name="Renewal Assessment Report">{{cite web | url=https://www.scribd.com/doc/238082730/Glyphosate-RAR-01-Volume-1-2013-12-18-San#scribd | title=Glyphosate RAR 01 Volume 1 2013-12-18 San | publisher=Hungry4Pesticides | work=Renewal Assessment Report | date=18 December 2013 | access-date=27 March 2015}}</ref><ref>{{cite web|archive-url=https://web.archive.org/web/20151014145339/http://www.bfr.bund.de/cm/349/frequently-asked-questions-on-the-health-assessment-of-glyphosate.pdf|archive-date=October 14, 2015|publisher=Bundesinstitut für Risikobewertung|date=15 January 2014|url=http://www.bfr.bund.de/cm/349/frequently-asked-questions-on-the-health-assessment-of-glyphosate.pdf|title=Frequently asked questions on the health assessment of glyphosate|url-status=dead|df=mdy-all}}</ref>
In November 2015, EFSA published its conclusion in the Renewal Assessment Report (RAR), stating it was "unlikely to pose a carcinogenic hazard to humans".<ref>{{cite journal | year = 2015 | title = Conclusion on the peer review of the pesticide risk assessment of the active substance glyphosate | journal = EFSA Journal| volume = 13 | issue = 11| page = 4302 | doi = 10.2903/j.efsa.2015.4302 | doi-access = free | author1 = European Food Safety Authority (EFSA) }}</ref> The ] was largely informed by this report when it made its decision on the use of glyphosate in November 2017.<ref name="theguardian.com">{{cite news|last1=Nelson|first1=Arthur|title=EU report on weedkiller safety copied text from Monsanto study|url=https://www.theguardian.com/environment/2017/sep/15/eu-report-on-weedkiller-safety-copied-text-from-monsanto-study|newspaper=The Guardian|access-date=September 30, 2017|date=September 14, 2017}}</ref>

EFSA's decision and the BfR report were criticized in an ] published by 96 scientists in November 2015 saying that the BfR report failed to adhere to accepted scientific principles of open and transparent procedures.<ref>{{cite news |url=http://www.dw.com/en/independent-scientists-warn-over-monsanto-herbicide/a-18886833 | title=Independent scientists warn over Monsanto herbicide| publisher=]| date=December 1, 2015| access-date=December 9, 2015}}</ref><ref name=portier>{{cite letter |recipient=Vytenis Andriukaitis | url = http://db.zs-intern.de/uploads/1448884347-151127_Portier_et_al_EFSA-Glyphosate-Letter.pdf | last = Portier | first = Christopher J. | display-authors=et al | subject=Open letter: Review of the Carcinogenicity of Glyphosate by EFSA and BfR | date = November 27, 2015 | access-date = December 9, 2015 }}</ref> The BfR report included unpublished data, lacked authorship, omitted references, and did not disclose conflict-of-interest information.<ref name=portier/>

In July 2023, EFSA re-evaluated after three years of assessment the putative impact of glyphosate on the health of humans, animals and the environment. As a result, no critical areas of concern were identified that would otherwise prevent glyphosate's registration renewal in the ].<ref>{{cite journal |last1=Alvarez |first1=Frenando |last2=Arena |first2=Maria |display-authors=1|title=Peer review of the pesticide risk assessment of the active substance glyphosate |journal=EFSA Journal |date=July 2023 |volume=7 |issue=21 |pages=e08164 |doi=10.2903/j.efsa.2023.8164|pmid=37502013 |pmc=10369247 }}</ref><ref>{{Cite web |date=2023-07-06 |title=Glyphosate: no critical areas of concern; data gaps identified {{!}} EFSA |url=https://www.efsa.europa.eu/en/news/glyphosate-no-critical-areas-concern-data-gaps-identified |access-date=2023-07-06 |website=www.efsa.europa.eu |language=en}}</ref><ref name="Open EFSA m798">{{cite web | title=Supporting documents for EFSA-Q-2020-00140 | website=Open EFSA | url=https://open.efsa.europa.eu/study-inventory/EFSA-Q-2020-00140 | access-date=25 August 2023}}</ref>

====International Agency for Research on Cancer====
In March 2015, the ] (IARC), an intergovernmental agency forming part of the ] of the ], published a summary of their forthcoming monograph on glyphosate, and classified glyphosate as "probably&nbsp;carcinogenic&nbsp;in humans" (category 2A) based on epidemiological studies, animal studies, and ''in vitro'' studies. It noted that there was "limited evidence" of carcinogenicity in humans for ].<ref name=NatureonWHO2015/><ref name=Lancet20March2015/><ref name=IARC20March2015>{{cite web | title = Press release: IARC Monographs Volume 112: evaluation of five organophosphate insecticides and herbicides | date = March 20, 2015 | url = http://www.iarc.fr/en/media-centre/iarcnews/pdf/MonographVolume112.pdf | publisher = International Agency for Research on Cancer, World Health Organization}}</ref><ref name=iarcmono/><ref>{{cite web | first1 = Michael | last1 = Specter | name-list-style = vanc | work = New Yorker | date = 10 April 2015 | url = http://www.newyorker.com/news/daily-comment/roundup-and-risk-assessment | title = Roundup and Risk Assessment | quote = 'Probable' means that there was enough evidence to say it is more than possible, but not enough evidence to say it is a carcinogen," Aaron Blair, a lead researcher on the IARC's study, said. Blair, a scientist emeritus at the National Cancer Institute, has studied the effects of pesticides for years. "It means you ought to be a little concerned about" glyphosate, he said.}}</ref> The IARC classifies substances for their carcinogenic potential, and "a few positive findings can be enough to declare a hazard, even if there are negative studies, as well." Unlike the BfR, it does not conduct a ], weighing benefits against risk.<ref>{{cite web | url = https://www.nytimes.com/2015/03/28/business/energy-environment/decades-after-monsantos-roundup-gets-an-all-clear-a-cancer-agency-raises-concerns.html | title = Weed Killer, Long Cleared, Is Doubted | first = Andrew | last = Pollack | name-list-style = vanc | date = 27 March 2015 | work = ]}}</ref>

The BfR responded that IARC reviewed only a selection of what they{{who|date=October 2020}} had reviewed earlier, and argued that other studies, including a cohort study called ''Agricultural Health Study'', do not support the classification.<ref>{{cite web | url = http://www.bfr.bund.de/cm/343/loest-glyphosat-krebs-aus.pdf | title = Löst Glyphosat Krebs aus? (announcement 007/2015)|date=23 March 2015|publisher=] | language = de}}</ref> The IARC report did not include unpublished studies, including one completed by the IARC panel leader.<ref>{{Cite news|url=https://www.motherjones.com/environment/2017/06/monsanto-roundup-glyphosate-cancer-who/|title=A scientist didn't disclose important data – and let everyone believe a popular weedkiller causes cancer | last = Butler | first = Kiera | name-list-style = vanc |date=June 15, 2017|work=]|access-date=2017-06-19|language=en-US}}</ref> The agency's international protocol dictates that only published studies be used in classifications of carcinogenicity,<ref>{{cite web | url = http://monographs.iarc.fr/ENG/Preamble/index.php | title = Preamble to the IARC Monographs | year = 2006 | publisher =]}}</ref> since national regulatory agencies including the EPA have allowed agrochemical corporations to conduct their own unpublished research, which may be biased in support of their profit motives.<ref>{{cite web | first1 = Sharon | last1 = Lerner| name-list-style = vanc | url = https://theintercept.com/2015/11/03/epa-used-monsanto-funded-research/| title = EPA used Monsanto's Research to Give Roundup A Pass | date=3 November 2015 | website=]|language=en-US}}</ref>

===== Reviews of the EFSA and IARC reports =====
A 2017 review done by personnel from EFSA and BfR argued that the differences between the IARC's and EFSA's conclusions regarding glyphosate and cancer were due to differences in their evaluation of the available evidence. The review concluded that "Two complementary exposure assessments ... suggests that actual exposure levels are below" the reference values identified by the EFSA "and do not represent a public concern."<ref name=Tarazona/>

In contrast, a 2016 analysis by Christopher Portier, a scientist advising the IARC in the assessment of glyphosate and advocate for its classification as possibly carcinogenic, concluded that in the EFSA's ''Renewal Assessment Report'', "almost no weight is given to studies from the published literature and there is an over-reliance on non-publicly available industry-provided studies using a limited set of assays that define the minimum data necessary for the marketing of a pesticide", arguing that the IARC's evaluation of ''probably carcinogenic to humans'' "accurately reflects the results of published scientific literature on glyphosate".<ref>{{cite journal | vauthors = Portier CJ, Armstrong BK, Baguley BC, Baur X, Belyaev I, Bellé R, Belpoggi F, Biggeri A, Bosland MC, Bruzzi P, Budnik LT, Bugge MD, Burns K, Calaf GM, Carpenter DO, Carpenter HM, López-Carrillo L, Clapp R, Cocco P, Consonni D, Comba P, Craft E, Dalvie MA, Davis D, Demers PA, De Roos AJ, DeWitt J, Forastiere F, Freedman JH, Fritschi L, Gaus C, Gohlke JM, Goldberg M, Greiser E, Hansen J, Hardell L, Hauptmann M, Huang W, Huff J, James MO, Jameson CW, Kortenkamp A, Kopp-Schneider A, Kromhout H, Larramendy ML, Landrigan PJ, Lash LH, Leszczynski D, Lynch CF, Magnani C, Mandrioli D, Martin FL, Merler E, Michelozzi P, Miligi L, Miller AB, Mirabelli D, Mirer FE, Naidoo S, Perry MJ, Petronio MG, Pirastu R, Portier RJ, Ramos KS, Robertson LW, Rodriguez T, Röösli M, Ross MK, Roy D, Rusyn I, Saldiva P, Sass J, Savolainen K, Scheepers PT, Sergi C, Silbergeld EK, Smith MT, Stewart BW, Sutton P, Tateo F, Terracini B, Thielmann HW, Thomas DB, Vainio H, Vena JE, Vineis P, Weiderpass E, Weisenburger DD, Woodruff TJ, Yorifuji T, Yu IJ, Zambon P, Zeeb H, Zhou SF | display-authors = 1 | title = Differences in the carcinogenic evaluation of glyphosate between the International Agency for Research on Cancer (IARC) and the European Food Safety Authority (EFSA) | journal = Journal of Epidemiology and Community Health | volume = 70 | issue = 8 | pages = 741–45 | date = August 2016 | pmid = 26941213 | pmc = 4975799 | doi = 10.1136/jech-2015-207005 }}</ref>

In October 2017, an article in ''The Times'' revealed that Portier had received consulting contracts with two law firm associations representing alleged glyphosate cancer victims that included a payment of US$160,000 to Portier.<ref>{{Cite news|url=https://www.faz.net/1.5248763|title=Herbizid: Der dramatische Kampf um die Deutungshoheit von Glyphosat|last=Grossarth|first=Jan|work=FAZ.NET|access-date=2019-01-06|language=de|issn=0174-4909}}</ref><ref>{{Cite news|url=https://www.thetimes.co.uk/article/weedkiller-scientist-was-paid-120-000-by-cancer-lawyers-v0qggbrk6|title=Weedkiller scientist was paid £120,000 by cancer lawyers|last=Webster|first=Ben |date=2017-10-18|work=The Times|access-date=2019-01-06|language=en|issn=0140-0460}}</ref> The IARC final report was also found to have changed compared to an interim report, through the removal of text saying certain studies had found glyphosate was not carcinogenic in that study's context, and through strengthening a conclusion of "limited evidence of animal carcinogenicity," to "sufficient evidence of animal carcinogenicity".<ref>{{Cite news|url=https://www.reuters.com/investigates/special-report/who-iarc-glyphosate/|title=Glyphosate: WHO cancer agency edited out|last=Kelland|first=Kate|website=Reuters|language=en|access-date=2019-01-06}}</ref>

====US Environmental Protection Agency====
In a 1993 review, the ], considered glyphosate to be ] and relatively low in ] and oral acute toxicity.<ref name="epa_reds">{{cite web | url = https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-417300_1-Sep-93.pdf | title = Registration Decision Fact Sheet for Glyphosate (EPA-738-F-93-011) | year = 1993 | work = R.E.D. FACTS | publisher = United States Environmental Protection Agency }}</ref> 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.<ref name="epa_reds" /> In 2015, the EPA initiated a review of glyphosate's toxicity and in 2016 reported that glyphosate is likely not carcinogenic.<ref name=NatureonWHO2015>{{cite journal | first1 = Daniel | last1 = Cressey | name-list-style = vanc | url = http://www.nature.com/news/widely-used-herbicide-linked-to-cancer-1.17181 | title = Widely used herbicide linked to cancer | journal = Nature | date = March 25, 2015 | doi = 10.1038/nature.2015.17181 | s2cid = 131732731 | doi-access = free }}</ref><ref>{{cite news |last=Charles|first=Dan | name-list-style = vanc |date=17 September 2016|title=EPA Weighs In On Glyphosate, Says It Doesn't Cause Cancer|url=https://www.npr.org/sections/thesalt/2016/09/17/494301343/epa-weighs-in-on-glyphosate-says-it-doesnt-cause-cancer|newspaper=]|access-date=19 September 2016}}</ref> In August 2019, the ] announced that it no longer allowed labels claiming glyphosate is a carcinogen, as those claims would "not meet the labeling requirements of the ]" and misinform the public.<ref name="auto">{{cite web |title=EPA Takes Action to Provide Accurate Risk Information to Consumers, Stop False Labeling on Products |url=https://www.epa.gov/newsreleases/epa-takes-action-provide-accurate-risk-information-consumers-stop-false-labeling |publisher=US EPA |access-date=28 October 2019 |language=en |date=8 August 2019}}</ref>

In 2017, evidence collected in a lawsuit brought against Monsanto by cancer patients revealed company emails which appeared to show a friendly relationship with a senior EPA official.<ref>{{cite web |last1=Charles |first1=Dan |title=Emails Reveal Monsanto's Tactics To Defend Glyphosate Against Cancer Fears |url=https://www.npr.org/sections/thesalt/2017/03/15/520250505/emails-reveal-monsantos-tactics-to-defend-glyphosate-against-cancer-fears |website=NPR |date=March 15, 2017 |access-date=May 14, 2019}}</ref>
===== Monsanto response and campaign =====
Monsanto called the IARC report biased and said it wanted the report to be retracted.<ref>{{cite web|url=https://www.reuters.com/article/us-monsanto-herbicide-idUSKBN0MK2GF20150324#TWrEqcrkJiYtdXgJ.97|title=Monsanto seeks retraction for report linking herbicide to cancer|last1=Gillam|first1=Carey|date=24 March 2015|work=Reuters|name-list-style=vanc}}</ref> In 2017, internal documents from Monsanto were made public by lawyers pursuing litigation against the company,<ref>{{Cite web|url=http://baumhedlundlaw.com/pdf/monsanto-documents/72-Document-Details-Monsantos-Goals-After-IARC-Report.pdf|title=Glyphosate: IARC (Monsanto shared document)|date=February 23, 2015|website=Baum Hedlund Law|access-date=2018-06-03}}</ref> who used the term "Monsanto papers" to describe the documents.<ref>{{cite web|url=https://www.baumhedlundlaw.com/toxic-tort-law/monsanto-roundup-lawsuit/monsanto-secret-documents/|title=Monsanto Papers: Secret Documents|publisher=Baum, Hedlund, Aristei & Goldman, PC|access-date=2019-10-31}}</ref> This term was later used also by ]<ref>{{Cite journal|last=McHenry|first=Leemon B.|date=2018|title=The Monsanto Papers: Poisoning the scientific well|journal=International Journal of Risk & Safety in Medicine|url=https://content.iospress.com/articles/international-journal-of-risk-and-safety-in-medicine/jrs180028|volume=29|issue=3–4|pages=193–205|doi=10.3233/JRS-180028|issn=1878-6847|pmid=29843257|s2cid=44179710 }}</ref> and others.<ref>{{Cite web|url=https://www.industrydocuments.ucsf.edu/chemical/collections/roundup-litigation-documents/|title=Chemical Industry Documents Library|language=en-US|access-date=2019-11-02}}</ref> The documents indicated Monsanto had planned a public relations effort to discredit the IARC report, and had engaged ] to write a 2015 opinion piece in '']'' challenging the report. Miller did not reveal the connection to Forbes, and according to the '']'', when Monsanto asked him if he was interested in writing such an article, he replied "I would be if I could start from a high-quality draft" provided by the company.<ref>{{Cite news|url=https://www.nytimes.com/2017/08/01/business/monsantos-sway-over-research-is-seen-in-disclosed-emails.html|title=Monsanto Emails Raise Issue of Influencing Research on Roundup Weed Killer|last=Hakim|first=Danny|date=2017-08-01|work=The New York Times|access-date=2019-10-26|language=en-US|issn=0362-4331}}</ref> Once this became public, Forbes removed his blog from their site.

Two journalists from '']'' won the 2018 ] for a series of articles on the documents, also titled ''Monsanto Papers''. Their reporting described, among other things, Monsanto's lawyers' letters demanding that IARC scientists turn over documents relating to ''Monograph 112'', which contained the IARC finding that glyphosate was a "probable carcinogen"; several of the scientists condemned these letters as intimidating.<ref name="EPP">{{cite web|website=European Press Prize|url=https://www.europeanpressprize.com/article/monsanto-papers/|author1=Stéphane Foucart|author2=Stéphane Horel|title= The Investigative Reporting Award 2018 Winner: Monsanto Papers|access-date=31 March 2019|quote=he non-American scientists who had been members of the IARC panel on glyphosate all received the same letter. Sent by Monsanto’s law firm, Hollingsworth, the letter told them to hand over all the files related to their work on ''Monograph 112''.}}</ref>

====California Office of Environmental Health Hazard Assessment====
In March 2015, the ] (OEHHA) announced plans to have glyphosate listed as a known carcinogen based on the IARC assessment. In 2016, Monsanto started a case against OEHHA and its acting director, Lauren Zeise,<ref>{{Cite news|title = Monsanto Sues California Over Herbicide Classification|url = https://www.nytimes.com/2016/01/22/business/monsanto-sues-california-over-herbicide-classification.html|newspaper = The New York Times|date=2016-01-21|access-date=2016-01-25|issn = 0362-4331|agency = Reuters}}</ref> but lost the suit in March 2017.<ref>{{Cite news|title=Monsanto loses cancer label lawsuit, accused of ghostwriting study|url = http://www.bizjournals.com/stlouis/news/2017/03/14/monsanto-loses-cancer-label-lawsuit-accused-of.html|newspaper = St. Louis Business Journal|date=2017-03-14|access-date=2017-06-28}}</ref>


Glyphosate was listed as "known to the State of California to cause cancer" in 2017, requiring warning labels under ].<ref>{{Cite web|url=https://oehha.ca.gov/proposition-65/crnr/glyphosate-listed-effective-july-7-2017-known-state-california-cause-cancer|title=Glyphosate Listed Effective July 7, 2017, as Known to the State of California to Cause Cancer |website=oehha.ca.gov|language=en|access-date=2017-07-07}}</ref> In February 2018, as part of an ongoing case, an injunction was issued prohibiting California from enforcing carcinogenicity labeling requirements for glyphosate until the case was resolved. The injunction stated that arguments by a ] for the ] " not change the fact that the overwhelming majority of agencies that that have examined glyphosate have determined it is not a cancer risk."<ref>{{cite news |title=Federal judge rules against California's attorney general over glyphosate |url=http://www.agweek.com/business/agriculture/4460533-federal-judge-rules-against-californias-attorney-general-over |access-date=14 August 2018 |publisher=AgWeek|date=14 June 2018|language=en}}</ref> In August 2019, the ] also said it no longer allowed labels claiming glyphosate is a carcinogen, as those claims would "not meet the labeling requirements of the ]" and misinform the public.<ref name="auto"/>
Some crops have been ] 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, but the development of similar resistance in some weed species is emerging as a costly problem. Soy was the first ].


====European Chemicals Agency====
== Chemistry ==
On March 15, 2017 the ] (ECHA) announced recommendations proceeding from a risk assessment of glyphosate performed by ECHA's Committee for Risk Assessment (RAC). Their recommendations maintained the current classification of glyphosate as a substance causing serious eye damage and as a substance toxic to aquatic life. However, the RAC did not find evidence implicating glyphosate to be a carcinogen, a mutagen, toxic to reproduction, nor toxic to specific organs.<ref>{{cite web|url=https://echa.europa.eu/-/glyphosate-not-classified-as-a-carcinogen-by-echa|title=Glyphosate not classified as a carcinogen by ECHA |website=echa.europa.eu}}</ref> In 2022, the agency reiterated these findings in a later review and stated on cancer risk that, "Based on a wide-ranging review of scientific evidence, the committee again concludes that classifying glyphosate as a carcinogen is not justified."<ref>{{cite web |title=Glyphosate: no change proposed to hazard classification|url=https://echa.europa.eu/sk/-/glyphosate-no-change-proposed-to-hazard-classification |website=echa.europa.eu |publisher=European Chemicals Agency |access-date=26 May 2023 |language=sk-SK}}</ref>
Glyphosate is an aminophosphonic analogue of the natural amino acid ], and the name is a contraction of '']'' '']''. The molecule has several dissociable hydrogens, especially the first hydrogen of the phosphate group. The molecule tends to exist as a ] where a phosphonic hydrogen dissociates and joins the amine group. Glyphosate is soluble in water to 12&nbsp;g/L at room temperature.


==Effects of use==
Glyphosate was first discovered to have herbicidal activity in 1970 by ], while working for Monsanto.<ref>{{cite journal | pmc = PMC33334 | doi = 10.1073/pnas.061025898 | title = Closing down on glyphosate inhibition---with a new structure for drug discovery | year = 2001 | author = Alibhai, M. F. | journal = Proceedings of the National Academy of Sciences | volume = 98 | page = 2944 | pmid = 11248008 | last2 = Stallings | first2 = WC | issue = 6}}</ref> Franz received the ] in 1987,<ref>] RECIPIENTS]</ref> and the ] for Applied Chemistry<ref>''People: Monsanto Scientist John E. Franz Wins 1990 Perkin Medal For Applied Chemistry'', The Scientist '''1990''', 4(10):28 ]]</ref> in 1990 for his discoveries.
===Emergence of resistant weeds===
In the 1990s, no ] weeds were known to exist.<ref name="NYT_2010" /> In 2005 a slow upward trend began, resistant weeds appearing rarely around the world.<ref name="Trends" /> Another ] occurred in 2011 and resistance accelerated globally.<ref name="Trends">
:{{cite journal|issue=2|year=2017|publisher=]|pages=48–60|last=Carvalho|volume=6|first=Fernando|journal=]|issn=2048-3694|s2cid=89994510|doi=10.1002/fes3.108|title=Pesticides, environment, and food safety|doi-access=free}}
:
:{{cite journal|issue=1|year=2016|publisher=]|last1=Peterson|volume=15|first1=John|last2=Antoniou|first2=Michael|last3=Blumberg|first3=Bruce|last4=Carroll|first4=Lynn|last5=Colborn|first5=Theo|last6=Everett|first6=Lorne|last7=Hansen|first7=Michael|last8=Landrigan|first8=Philip|last9=Lanphear|first9=Bruce|last10=Mesnage|first10=Robin|last11=Vandenberg|first11=Laura|last12=vom Saal|first12=Frederick|last13=Welshons|first13=Wade|last14=Benbrook|first14=Charles|journal=]|issn=1476-069X|s2cid=10631819|doi=10.1186/s12940-016-0117-0|title=Concerns over use of glyphosate-based herbicides and risks associated with exposures: a consensus statement|page=19 |pmid=26883814 |pmc=4756530 |bibcode=2016EnvHe..15...19M |doi-access=free }}
:
:These reviews cite this research.
:
:{{cite journal|issue=1|year=2016|publisher=]|volume=28|last=Benbrook|first=Charles|journal=]|issn=2190-4707|s2cid=1660085|doi=10.1186/s12302-016-0070-0|title=Trends in glyphosate herbicide use in the United States and globally|page=3 |pmid=27752438 |pmc=5044953 |doi-access=free }}
</ref> By 2014, glyphosate-resistant weeds dominated herbicide-resistance research. At that time, 23 glyphosate-resistant species were found in 18 countries.<ref name="springer_2016_heap_2014" /> "Resistance evolves after a weed population has been subjected to intense selection pressure in the form of repeated use of a single herbicide."<ref name="NYT_2010">{{cite news| url=https://www.nytimes.com/2010/05/17/opinion/17mon3.html?ref=opinion | work=The New York Times | title=Resisting Roundup | date=May 16, 2010 |access-date=March 24, 2016}}</ref><ref name="canada"/>


According to Ian Heap, a weed specialist, who completed his PhD on resistance to multiple herbicides in annual ryegrass ('']'') in 1988<ref name="Heap_PhD_1988">{{cite book | title=Resistance to herbicides in annual ryegrass (Lolium Rigidum) | publisher=Department of Agronomy, ] | date=1988 | author=Heap, Ian Michael | location=Adelaide}}</ref> – the first case of an herbicide-resistant weed in Australia<ref name="agannex_2015">{{cite web | url=http://www.agannex.com/weeds/history-of-herbicide-resistance | title=History of herbicide resistance Herbicide resistance: Then, now, and the years to come | date=June 2015 | access-date=24 March 2016 | author=King, Carolyn | archive-date=July 3, 2015 | archive-url=https://web.archive.org/web/20150703010649/http://www.agannex.com/weeds/history-of-herbicide-resistance | url-status=dead }}</ref> – by 2014 ''Lolium rigidum'' was the "world’s worst herbicide-resistant weed" with instances in "12 countries, 11 sites of action, 9 cropping regimens" and affecting "over 2 million hectares."<ref name="springer_2016_heap_2014">{{cite book |doi=10.1007/978-94-007-7796-5_12 |chapter=Herbicide Resistant Weeds |title=Integrated Pest Management |pages=281–301 |year=2014 |last1=Heap |first1=Ian |publisher=Springer |location=Dordrecht |isbn=978-94-007-7795-8 }}</ref> Annual ryegrass has been known to be resistant to herbicides since 1982. The first documented case of glyphosate-resistant ''L. rigidum'' was reported in Australia in 1996 near ].<ref name="weeds_iastate_1998">{{citation |url=http://www.weeds.iastate.edu/mgmt/2003/glyresistance.shtml |series=Weed Science Online |title=Are Roundup Ready Weeds in Your Future II |first=Bob |last=Hartzler |name-list-style=vanc |date=January 29, 2003 |access-date=March 24, 2016 |work=Iowa State University (ISU) |archive-date=March 5, 2016 |archive-url=https://web.archive.org/web/20160305021727/http://www.weeds.iastate.edu/mgmt/2003/glyresistance.shtml |url-status=dead }}</ref><ref>{{cite journal | vauthors = Powles SB, Lorraine-Colwill DF, Dellow JJ, Preston C | year = 1998 | title = Evolved Resistance to Glyphosate in Rigid Ryegrass (Lolium rigidum) in Australia | journal = Weed Science | volume = 46 | issue = 5 | pages = 604–07 | jstor = 4045968 | doi = 10.1017/S0043174500091165 | s2cid = 83591923 }}</ref><ref name=ResistanceBook2010>Glyphosate Resistance in Crops and Weeds: History, Development, and Management. Editor, Vijay K. Nandula. John Wiley & Sons, 2010 {{ISBN|978-1118043547}}</ref> In 2006, farmers associations were reporting 107 biotypes of weeds within 63 weed species with herbicide resistance.<ref name="SEFarmPressResistance">{{Cite web|url=http://southeastfarmpress.com/glyphosate-resistant-weeds-reality-cotton-growers/ |title=Glyphosate resistance is a reality that should scare some cotton growers into changing the way they do business |publisher=Southeastfarmpress.com |access-date=2010-08-22|date=February 10, 2006 }}</ref> In 2009, Canada identified its first resistant weed, ], and at that time 15 weed species had been confirmed as resistant to glyphosate.<ref name="canada">{{Cite web|author=Lori |url=http://www.uoguelph.ca/news/2009/05/u_of_g_research_19.html |title=U of G Researchers Find Suspected Glyphosate-Resistant Weed |publisher=Uoguelph.ca |date=2009-05-07 |access-date=2010-08-22}}</ref><ref name="WeedScience-resistance">{{cite web |url=http://weedscience.org/Summary/MOA.aspx?MOAID=12 | title = List of Herbicide Resistant Weeds by Herbicide Mode of Action - Weeds Resistant to EPSP synthase inhibitors (G/9) | publisher=]|website=The International Survey of Herbicide Resistant Weeds | year=2020 | access-date=22 November 2020 | vauthors = Heap I}}</ref> As of 2010, in the United States {{convert|7|to|10|e6acre|e6ha|abbr=off}} of soil were afflicted by herbicide-resistant weeds, or about 5% of the 170 million acres planted with corn, soybeans, and cotton, the crops most affected, in 22 states.<ref name="nytimes">{{Cite news|url=https://www.nytimes.com/2010/05/04/business/energy-environment/04weed.html|title=U.S. Farmers Cope With Roundup-Resistant Weeds | vauthors = Neuman W, Pollack A | date = 4 May 2010 | work = ] | pages = B1 | access-date = 4 May 2010 | location = New York }}</ref> In 2012, Charles Benbrook reported that the ] listed 22 herbicide-resistant species in the U.S., with over {{convert|5.7|e6ha|e6acre|abbr=on}} infested by GR weeds and that ] had carried out a survey and reported a figure of around {{convert|40|e6ha|e6acre|sigfig=1|abbr=on}}.<ref name=Benbrook2012>{{cite journal |doi=10.1186/2190-4715-24-24 |title=Impacts of genetically engineered crops on pesticide use in the U.S. – the first sixteen years |journal=Environmental Sciences Europe |volume=24 |pages=24 |year=2012 |last1=Benbrook |first1=Charles M |issue=1 |doi-access=free }}</ref> The International Survey of Herbicide Resistant Weeds database lists species that are resistant to glyphosate.<ref name="WeedScience-resistance" />
In an editorial on May 17, 2010, the ] noted the appearance of glyphosate-resistant weeds.<ref name="nytimes.com">{{cite news| url=http://www.nytimes.com/2010/05/17/opinion/17mon3.html?ref=opinion | work=The New York Times | title=Resisting Roundup | date=May 16, 2010}}</ref>


In response to resistant weeds, farmers are hand-weeding, using tractors to turn over soil between crops, and using other herbicides in addition to glyphosate.
=== 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:<ref></ref> 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%).<ref></ref> These products may contain other ingredients, causing them to have different effects. For example, Roundup was found to have different effects to glyphosate alone.<ref name=Richard2005/> Roundup is a water-based solution containing glyphosate, a ], and other substances. Other formulations contain additional active ingredients to improve the speed of action. In the UK, Weedol Rootkill Plus, which contains glyphosate and pyraflufen-ethyl, and ]<ref></ref> which contains glyphosate and ], are available.


Monsanto scientists have found that some resistant weeds have as many as 160 extra copies of a gene called ''],'' the enzyme glyphosate disrupts.<ref>{{cite web | title = With BioDirect, Monsanto Hopes RNA Sprays Can Someday Deliver Drought Tolerance and Other Traits to Plants on Demand | work = ] | url = http://www.technologyreview.com/featuredstory/540136/the-next-great-gmo-debate | access-date = 2015-08-31}}</ref>
== Biochemistry ==
Glyphosate kills plants by interfering with the synthesis of the amino acids ], ] and ]. It does this by inhibiting the ] 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), which ] the reaction of ]-3-phosphate (S3P) and ] to form 5-enolpyruvyl-shikimate-3-phosphate (ESP). ESP is subsequently ] to ], an essential precursor in plants for the ] ]s: ], ] and ].<ref>Purdue University, Department of Horticulture and Landscape Architecture, Metabolic Plant Physiology Lecture notes, Aromatic amino acid biosynthesis, The shikimate pathway - synthesis of chorismate.</ref><ref>Saccharomyces Genome Database - S. cerevisiae Pathway: chorismate biosynthesis </ref> These amino acids are used as building blocks in ]s, and to produce secondary metabolites such as ]s, ]s and ]. 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.<ref>E. Schönbrunn et al., Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail, PNAS 2001,98:1376–1380 </ref> The ] 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,<ref>(Su , L.Y. et al. 1992. The relationship of glyphosate treatment to sugar metabolism in sugarcane: New physiological insights. J. Plant Physiol. 140:168-173.)</ref><ref>(Lamb, D.C. et al. 1998. 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. 244:110114.)</ref> and also has been found to affect animal enzymes.<ref>(Hietanen, E., K. Linnainmaa, and H. Vainio. 1983. Effects of phenoxy herbicides and glyphosate on the hepatic and intestinal biotransformation activities in the rat. Acta Pharma. et Toxicol. 53:103-112.)</ref>


== Use == ====Palmer amaranth====
] (''Amaranthus palmeri'')]]
]
In 2004, a glyphosate-resistant variation of ] was found in the U.S. state of Georgia.<ref name="Culpepper">{{cite journal |doi=10.1614/WS-06-001R.1 |title= Glyphosate-resistant Palmer amaranth (''Amaranthus palmeri'') confirmed in Georgia |year=2006 |vauthors=Culpepper AS, Grey TL, Vencill WK, Kichler JM, Webster TM, Brown SM, York AC, Davis JW, Hanna WW |s2cid= 56236569 | journal =] | volume = 54 | issue = 4 | pages = 620–26 | jstor = 4539441 }}</ref> In 2005, resistance was also found in North Carolina.<ref name="Hampton">{{cite web | url = http://www.cals.ncsu.edu/agcomm/magazine/winter09/cotton.html | title = Cotton versus the monster weed| last= Hampton |first = Natalie |date = Winter 2009|website = College of Agriculture and Life Science|publisher = North Carolina State University}}</ref> The species can quickly become resistant to multiple herbicides and has developed multiple mechanisms for glyphosate resistance due to ].<ref>{{cite journal |last1=Ward |first1=Sarah M. |last2=Webster |first2=Theodore M. |last3=Steckel |first3=Larry E. |title=Palmer Amaranth (''Amaranthus palmeri''): A Review |journal=]|date=20 January 2017 |volume=27 |issue=1 |pages=12–27 |doi=10.1614/WT-D-12-00113.1|s2cid=84142912 |doi-access=free }}</ref><ref name="Hampton"/> The glyphosate-resistant weed variant is now widespread in the southeastern United States.<ref name="Culpepper"/><ref name="FS03Mar09">{{cite news | url = http://magissues.farmprogress.com/TFS/FS03Mar09/tfs024.pdf | title = Resistance a growing problem | vauthors = Smith JT | date = March 2009 | work = The Farmer Stockman | access-date = 2009-07-19 | archive-date = July 10, 2011 | archive-url = https://web.archive.org/web/20110710224650/http://magissues.farmprogress.com/TFS/FS03Mar09/tfs024.pdf | url-status = dead }}</ref> Cases have also been reported in Texas<ref name="FS03Mar09"/> and Virginia.<ref>{{cite web | url = http://agfax.com/news/2009/peanutfax/0716pf.htm | title = Peanuts: variable insects, variable weather, Roundup resistant Palmer in new state | vauthors = Taylor O | date = 2009-07-16 | work =]| publisher =]| access-date = 2009-07-19 | archive-date = July 7, 2011 | archive-url = https://web.archive.org/web/20110707093545/http://agfax.com/news/2009/peanutfax/0716pf.htm | url-status = dead }}</ref>
Glyphosate is effective in killing a wide variety of plants, including ]es, ], and ]s.<ref name="greenpeace">''Greenpeace''. (1997). </ref> It has a relatively small effect on some clover species.<ref></ref> By volume, it is one of the most widely used herbicides.<ref name="epa tech">U.S. Environmental Protection Agency. (2006). Technical Factsheet on: GLYPHOSATE </ref> It is commonly used for ], ], and ] purposes, as well as garden maintenance (including home use).<ref name="epa tech"/>


====''Conyza'' species====
Glyphosate is supplied in several formulations for different uses:
]]]
'']'' (also known as hairy fleabane and buva) and '']'' (known as horseweed or marestail) are other weed species that have lately developed glyphosate resistance.<ref>{{cite journal |doi=10.1590/S0100-83582007000300017 |title=Buva (''Conyza bonariensis'') resistente ao glyphosate na região sul do Brasil |trans-title=''Conyza bonariensis'' biotypes resistant to the glyphosate in southern Brazil |language=pt |year=2007 |vauthors=Vargas L, Bianchi MA, Rizzardi MA, Agostinetto D, Dal Magro T |journal=Planta Daninha |volume=25 |issue=3 |pages=573–78|doi-access=free }}</ref><ref>{{cite journal |doi=10.1614/WS-05-010R |title=Assessment of two nondestructive assays for detecting glyphosate resistance in horseweed (''Conyza canadensis'') |year=2005 |vauthors=Koger CH, Shaner DL, Henry WB, Nadler-Hassar T, Thomas WE, Wilcut JW |s2cid=198128423 | journal =]| volume = 53 | issue = 4 | pages = 438–45 | jstor = 4047050}}</ref><ref name="pmid20063320">{{cite journal | vauthors = Ge X, d'Avignon DA, Ackerman JJ, Sammons RD | title = Rapid vacuolar sequestration: the horseweed glyphosate resistance mechanism | journal = ] | volume = 66 | issue = 4 | pages = 345–48 | date = Apr 2010 | pmid = 20063320 | pmc = 3080097 | doi = 10.1002/ps.1911 }}</ref> A 2008 study on the current situation of glyphosate resistance in South America concluded "resistance evolution followed intense glyphosate use" and the use of glyphosate-resistant soybean crops is a factor encouraging increases in glyphosate use.<ref name="pmid18161884">{{cite journal | vauthors = Vila-Aiub MM, Vidal RA, Balbi MC, Gundel PE, Trucco F, Ghersa CM | title = Glyphosate-resistant weeds of South American cropping systems: an overview | journal =]| volume = 64 | issue = 4 | pages = 366–71 | date = Apr 2008 | pmid = 18161884 | doi = 10.1002/ps.1488 }}</ref> In the 2015 growing season, glyphosate-resistant marestail proved to be especially problematic to control in Nebraska production fields.<ref name=cw-marestail>{{cite news|last1=Jhala|first1=Amit|title=Post-Emergence Herbicide Options for Glyphosate-Resistant Marestail in Corn and Soybean|url=http://cropwatch.unl.edu/controlling-glyphosate-resistant-marestail|access-date=17 August 2015|agency=]|publisher=]|date=4 June 2015 | name-list-style = vanc }}</ref>


====Ryegrass====
* Ammonium salt.
]]]
* Isopropyl amine salt.
Glyphosate-resistant ] (''Lolium'') has occurred in most of the Australian agricultural areas 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 resistant ryegrass does not compete well against nonresistant plants and their numbers decrease when not grown under conditions of glyphosate application.<ref>{{cite journal | title = A Decade of Glyphosate-Resistant Lolium around the World: Mechanisms, Genes, Fitness, and Agronomic Management |year=2009 |vauthors=Preston C, Wakelin AM, Dolman FC, Bostamam Y, Boutsalis P |s2cid=85725624 | journal =]| volume = 57 | issue = 4 | pages = 435–41 | doi = 10.1614/WS-08-181.1 }}</ref>
* Glyphosate acid - standalone, as ammonium salt or as isopropyl salt.
* Potassium salt


====Johnson grass====
Products are supplied most commonly in formulations of 120, 240, 360, 480 and 680&nbsp;g active ingredient per litre. The most common formulation in agriculture is 360&nbsp;g, either alone or with added cationic surfactants.
Glyphosate-resistant ] (''Sorghum halepense'') has been found in Argentina as well as Arkansas, Louisiana, and Mississippi.<ref>{{cite journal |last1=Peerzada |first1=Arslan Masood |last2=Ali |first2=Hafiz Haider |last3=Hanif |first3=Zarka |last4=Bajwa |first4=Ali Ahsan |last5=Kebaso |first5=Lynda |last6=Frimpong |first6=David |last7=Iqbal |first7=Nadeem |last8=Namubiru |first8=Halima |last9=Hashim |first9=Saima |last10=Rasool |first10=Ghulam |last11=Manalil |first11=Sudheesh |last12=van der Meulen |first12=Annemieke |last13=Chauhan |first13=Bhagirath Singh |display-authors=1|title=Eco-biology, impact, and management of ''Sorghum halepense'' (L.) Pers. |journal=]|date=16 March 2017 |volume=25 |issue=4 |pages=955–973 |doi=10.1007/s10530-017-1410-8|s2cid=17096998 |url=https://espace.library.uq.edu.au/view/UQ:547820/UQ547820_OA.pdf }}</ref>


===Monarch butterfly populations===
For 360&nbsp;g formulations, European regulations allow applications of up to 12 litres per hectare for control of perennial weeds such as ]. More commonly, rates of 3 litres per hectare are practiced for control of annual weeds between crops.<ref></ref>
Use of glyphosate and other herbicides like ] to clear ] along roads and fields may have contributed to a decline in ] populations in the Midwestern United States.<ref>{{cite web |url=http://weedcontrolfreaks.com/2014/02/are-herbicides-responsible-for-the-decline-in-monarch-butterflies/ |title=Are herbicides responsible for the decline in Monarch butterflies? |last1=Kniss |first1=Andrew |name-list-style=vanc |date=2014-02-10 |website=Control Freaks |access-date=2016-06-16 |quote=The evidence seems clear that the number of milkweed plants through this region has indeed declined. The cause for the milkweed decline, though, is a little less certain. |archive-date=August 29, 2016 |archive-url=https://web.archive.org/web/20160829045127/http://weedcontrolfreaks.com/2014/02/are-herbicides-responsible-for-the-decline-in-monarch-butterflies/ |url-status=dead }}</ref> Along with deforestation and adverse weather conditions,<ref>{{cite news |url=https://www.washingtonpost.com/news/wonk/wp/2014/01/29/the-monarch-butterfly-population-just-hit-a-record-low-heres-why/ |title=Monarch butterflies keep disappearing. Here's why. |last=Plumer |first=Brad | name-list-style = vanc |date=January 29, 2014 |newspaper=The Washington Post |access-date=2016-06-16}}</ref> the decrease in milkweed contributed to an 81% decline in monarchs.<ref>{{cite journal |doi=10.1111/j.1752-4598.2012.00196.x |title=Milkweed loss in agricultural fields because of herbicide use: Effect on the monarch butterfly population |journal=]|volume=6 |issue=2 |pages=135–44 |year=2013 |last1=Pleasants |first1=John M |last2=Oberhauser |first2=Karen S |s2cid=14595378 |url=http://osf.io/wmj6e | name-list-style = vanc }}</ref><ref>{{cite journal |doi=10.1016/s0261-2194(00)00024-7 |title=Occurrence of common milkweed (Asclepias syriaca) in cropland and adjacent areas |journal=]|volume=19 |issue=5 |pages=363–66 |year=2000 |last1=Hartzler |first1=Robert G |last2=Buhler |first2=Douglas D |bibcode=2000CrPro..19..363H | name-list-style = vanc |url=https://lib.dr.iastate.edu/agron_pubs/32 }}</ref> The ] (NRDC) filed a suit against the ] in 2015, in which it argued that the agency ignored warnings about the potentially dangerous impacts of glyphosate usage on monarchs.<ref>{{cite web | title = NRDC Sues EPA Over Demise of Monarch Butterfly Population | url = http://www.nbcnews.com/science/environment/nrdc-sues-epa-over-demise-monarch-butterfly-population-n314371 | year = 2015 | work = NBC }}</ref>


==Legal status==
=== Genetically modified crops ===
Glyphosate was first approved for use in the 1970s, and as of 2010 was labelled for use in 130 countries.<ref name=Dill/>{{rp|2}}
In 1996, genetically modified soybeans were made commercially available.<ref></ref> Current ''Roundup Ready'' crops include ], ] (corn), ], ], ], and ], with ] still under development. These cultivars greatly improved conventional farmers' ability to control ]s, since glyphosate could be sprayed on fields without damaging the crop. As of 2005, 87% of U.S. soybean fields were planted with glyphosate-resistant varieties.<ref>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, p. 13 </ref><ref>National Agriculture Statistics Service (2005) in Acreage eds. Johanns, M. & Wiyatt, S. D. 6 30, (U.S. Dept. of Agriculture, Washington, DC).</ref>


In 2017 Vandenberg ''et al.'' cited a 100-fold increase in the use of glyphosate-based herbicides from 1974 to 2014, the possibility that herbicide mixtures likely have effects that are not predicted by studying glyphosate alone, and reliance of current safety assessments on studies done over 30 years ago. They recommended that current safety standards be updated, writing that the current standards "may fail to protect public health or the environment."<ref>{{cite journal|url= |title=Is it time to reassess current safety standards for glyphosate-based herbicides?|vauthors=Vandenberg LN, Blumberg B, Antoniou MN, Benbrook CM, Carroll L, Colborn T, Everett LG, Hansen M, Landrigan PJ, Lanphear BP, Mesnage R, vom Saal FS, Welshons WV, Myers JP|date=June 2017|journal=]|volume=71|issue=6|pages=613–18|doi=10.1136/jech-2016-208463|pmid=28320775|pmc=5484035}}</ref>
While the use of ''Roundup Ready'' crops may have increased the usage of herbicides measured in pounds applied per acre,<ref name="Benbrook">Charles Benbrook. . Ag BioTech InfoNet Technical Paper Number 1</ref> its use has changed the herbicide use profile away from ], metribuzin, and ]. This has the benefit of reducing the dangers of herbicide runoff into drinking water.<ref>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</ref><ref>{{cite journal |author=Shipitalo MJ, Malone RW, Owens LB |title=Impact of glyphosate-tolerant soybean and glufosinate-tolerant corn production on herbicide losses in surface runoff |journal=] |volume=37 |issue=2 |pages=401–8 |year=2008 |pmid=18268303 |doi=10.2134/jeq2006.0540 |url=}}</ref>


===Europe===
In 1999, a review of ''Roundup Ready'' soybean crops found that, compared to the top conventional varieties, they had a 6.7% lower yield.<ref name="Benbrook" /> This "yield drag" is similar to what is observed when other traits are introduced into soybeans by conventional breeding <ref>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</ref> and may not be due to the ''Roundup Ready'' trait or the genetically modified nature of the crop since Monsanto has recently released ''Roundup Ready'' 2 soybeans, which are claimed to yield 7–11% higher than RR version 1.<ref>Roundup Ready 2 Yield- Monsanto Web site http://www.monsanto.com/rr2y/</ref> There have been no reports of "yield drag" with the other ''Roundup Ready'' crops maize, sorghum or canola.
In April 2014, the legislature of the ] passed legislation prohibiting sale of glyphosate to individuals for use at home; commercial sales were not affected.<ref>Staff, Sustainable Pulse. Apr 4 2014 </ref>


In June 2015, the ] asked nurseries and garden centers to halt over-the-counter sales of glyphosate in the form of Monsanto's Roundup. This was a nonbinding request and all sales of glyphosate remain legal in France until 2022, when it was planned to ban the substance for home gardening.<ref name="url_Reuters_France">{{cite news | url = https://www.reuters.com/article/france-monsanto-idUSL5N0Z00H120150614?type=companyNews | title = French minister asks shops to stop selling Monsanto Roundup weedkiller | newspaper = ] | date = June 14, 2015 }}</ref> However, subsequently the French parliament decided to not to impose a definitive date for such a ban.<ref>
=== Development ===
French parliament does not vote for a date to terminate glyphosate:
Some micro-organisms have a version of 5-enolpyruvoyl-shikimate-3-phosphate synthetase (EPSPS) that is resistant to glyphosate inhibition. The version used in ] was isolated from '']'' strain CP4 (CP4 EPSPS) that was resistant to glyphosate.<ref>{{cite journal | doi = 10.2135/cropsci2005.0329 | title = Development and Characterization of a CP4 EPSPS-Based, Glyphosate-Tolerant Corn Event | author = G. R. Heck, ''et al.'' | journal = ] | volume = 45 | pages = 329–339 | date=1 January 2005| url = http://crop.scijournals.org/cgi/content/full/45/1/329 | format = Free full text | issue = 1 }}</ref><ref>{{cite journal | title = Molecular basis for the herbicide resistance of Roundup Ready crops | author = T. Funke ''et al.'' | journal = ] | year = 2006 | volume = 103 | pages = 13010–13015 | url = http://www.pnas.org/cgi/content/full/103/35/13010 | format = Free full text | doi = 10.1073/pnas.0603638103 | pmid = 16916934 | issue = 35 | pmc = 1559744}}</ref> This CP4 EPSPS gene was ] and ] into ]. The CP4 EPSPS gene was engineered for plant ] by ] the 5' end of the gene to a ] ] derived from the ] EPSPS. This transit peptide was used because it had shown previously an ability to deliver bacterial EPSPS to the chloroplasts of other plants. The ] used to move the gene into soybeans was PV-GMGTO4. It contained three bacterial genes, two PC4 EPSPS genes, and a gene ] ] (]) from '']'' as a marker. The DNA was injected into the soybeans using the ]. Soybean cultivar A54O3 was used for the ]. 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 ] into a blue ]. Those plants that showed GUS expression were then taken and sprayed with glyphosate, and their tolerance was tested over many generations.
</ref> In January 2019, "the sale, distribution, and use of Roundup 360 s banned" in France. Exemptions for many farmers were later implemented, and a curb of its use by 80% for 2021 is projected.<ref>{{Cite web|url=https://www.france24.com/en/20190116-weedkiller-roundup-banned-france-after-court-ruling|title=Weedkiller Roundup banned in France after court ruling|date=2019-01-16|website=France 24|language=en|access-date=2019-01-16}}</ref><ref name=FrenchBan>{{cite news|newspaper=Reuters|title=French court cancels Monsanto weedkiller permit on safety grounds|date=15 January 2019|access-date=16 January 2019|url=https://www.reuters.com/article/us-bayer-monsanto-france/french-court-cancels-monsanto-weedkiller-permit-on-safety-grounds-idUSKCN1P91F6}}</ref>


A vote on the relicensing of glyphosate in the EU stalled in March 2016. Member states France, Sweden, and the Netherlands objected to the renewal.<ref>{{cite news|url=https://www.theguardian.com/environment/2016/mar/08/eu-vote-on-controversial-weedkiller-licence-postponed-glyphosate|title=Vote on controversial weedkiller's European licence postponed|author=Arthur Nelson|newspaper=The Guardian|date=2016-03-08}}</ref> A vote to reauthorize on a temporary basis failed in June 2016<ref>{{cite news|url=https://www.theguardian.com/environment/2016/jun/06/recall-of-monsantos-roundup-likely-as-eu-refuses-limited-use-of-glyphosate|title=Recall of Monsanto's Roundup likely as EU refuses limited use of glyphosate|agency=Reuters|date=2016-06-06}}</ref> but at the last minute the license was extended for 18 months until the end of 2017.<ref>{{cite news|url=https://www.theguardian.com/business/2016/jun/29/controversial-chemical-roundup-weedkiller-escapes-immediate-ban|title=Controversial chemical in Roundup weedkiller escapes immediate ban|author=Arthur Nelson|newspaper=]|date=2016-06-29}}</ref>
== Other uses ==
]
Glyphosate is one of a number of herbicides used by the ] government to spray ]n ] fields through ]. Its effects on legal crops and effectiveness in fighting the ] have been disputed.<ref>{{Failed verification|date=August 2010}}</ref> 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 ], which have been ] to be both "Roundup Ready" and larger and higher yielding than the original strains of the plant.<ref>{{Dead link|date=August 2010}}</ref> 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.{{Citation needed|date=August 2010}}


On 27 November 2017, in the ] a majority of eighteen member states voted in favor of permitting the use of glyphosate for five more years. A ] of sixteen states representing 65% of EU citizens was required to pass the law.<ref>
== Effects ==
. '']'' {{in lang|nl}}, 28 November 2017.</ref> The German Minister of Agriculture, ], unexpectedly voted in favor while the German coalition government was internally divided on the issue which usually results in Germany abstaining.<ref> {{in lang|nl}}. '']'', 28 November 2017.</ref>


In December 2018, attempts were made to reopen the decision to license the weed-killer. These were condemned by Conservative MEPs, who said the proposal was politically motivated and flew in the face of scientific evidence.<ref>{{cite news |title= Move to re-open Glyphosate case attacked by Conservative MEPs |url= http://conservativeeurope.com/news/move-to-re-open-glyphosate-case-attacked-by-conservative-meps |work= Conservative Europe |date= 6 December 2018 |access-date= January 30, 2019 |archive-date= January 30, 2019 |archive-url= https://web.archive.org/web/20190130162344/http://conservativeeurope.com/news/move-to-re-open-glyphosate-case-attacked-by-conservative-meps |url-status= dead }}</ref>
Glyphosate is rated least dangerous in comparison to other herbicides and pesticides, such as those from the ] family.<ref></ref> Roundup has a ] (EPA) ] of III (on a I to IV scale, where IV is least dangerous) for oral and inhalation exposure.<ref name="epa_reds">U.S. EPA ReRegistration Decision Fact Sheet for Glyphosate (EPA-738-F-93-011) 1993. </ref> It does not bioaccumulate, and breaks down rapidly in the environment.<ref>http://www.monsanto.com/products/Documents/glyphosate-background-materials/gly_human_risk.pdf</ref>


In March 2019, the ] (ECJ) ordered the ] (EFSA) to release all carcinogenicity and toxicity pesticide industry studies on glyphosate to the general public.<ref>, 7 March 2019.</ref>
=== Humans ===
]) are very rare, but possible]]


In March 2019, the ] of ] outlawed the private use of glyphosate in residential areas while the commercial application of the herbicide is still permitted for farmers. The use of glyphosate by public authorities and road maintenance crews was already halted a number of years prior to the current ban by local authorities.<ref> (in German). ''Die Presse''. Retrieved 29 April 2019.</ref>
The ] considers glyphosate to be relatively low in toxicity, and without carcinogenic or teratogenic effects.<ref name="autogenerated7">http://www.epa.gov/oppsrrd1/REDs/factsheets/0178fact.pdf</ref> The EPA considered a "worst case" dietary risk model of an individual eating a lifetime of food entirely from glyphosate-sprayed fields, and with residue levels remaining at their maximum levels, and concluded that no adverse effects would exist under these conditions<ref name="autogenerated7"/>
In 2007, the EPA selected glyphosate for further screening for endocrinal disruptor effects.<ref>USEPA Federal Register http://www.epa.gov/endo/pubs/draft_list_frn_061807.pdf</ref><ref>Accustandard, Chemical Reference Standards, http://www.accustandard.com/asi/np_endocrine_disruptors.php3</ref>


In June 2019, ] and ] announced that glyphosate and other commonly used herbicides for weed eradication along railway tracks will be phased out by 2025, while more environmentally sound methods for vegetation control are implemented.<ref>Briner M (July 2018). {{Webarchive|url=https://web.archive.org/web/20190627064202/https://www.aargauerzeitung.ch/wirtschaft/schluss-mit-glyphosat-sbb-wollen-unkraut-anders-vernichten-132845313 |date=June 27, 2019 }} ''Aargauer Zeitung'' (in German). Retrieved 26 June 2019.</ref><ref>Schlesiger Ch (June 2019). ''Wirtschaftswoche'' (in German). Retrieved 26 June 2019.</ref>
Laboratory toxicology studies suggest that other ingredients combined with glyphosate may have greater toxicity than glyphosate alone. For example, a study comparing glyphosate and ] found that Roundup had a greater effect on ] than glyphosate alone.<ref name=Richard2005>{{cite journal |author=Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE |title=Differential effects of glyphosate and roundup on human placental cells and aromatase |journal=] | format = Free full text | volume=113 |issue=6 |pages=716–20 |year=2005 |month=June |pmid=15929894 |pmc=1257596 |doi= 10.1289/ehp.7728|url=http://ehpnet1.niehs.nih.gov/members/2005/7728/7728.html}}</ref> Another study has shown that Roundup formulations and metabolic products cause the death of human embryonic, placental, and umbilical cells '']'' even at low concentrations. The effects are not proportional to Glyphosate concentrations but dependent on the nature of the ]s used in the formulation.<ref name="human cells">{{cite journal|last=Benachour|first=Nora |coauthors=Gilles-Eric Séralini|date=December 23, 2008|title=Glyphosate Formulations Induce Apoptosis and Necrosis in Human Umbilical, Embryonic, and Placental Cells|journal=Chemical Research in Toxicology|url=http://pubs.acs.org/doi/abs/10.1021/tx800218n|doi=10.1021/tx800218n|volume=22|page=97|pmid=19105591|issue=1}}</ref>
Statistics from the ]'s Pesticide Illness Surveillance Program indicate that glyphosate-related incidents are one of the highest reported of all pesticides.<ref>G{{cite journal |author=Goldstein DA, Acquavella JF, Mannion RM, Farmer DR |title=An analysis of glyphosate data from the California Environmental Protection Agency Pesticide Illness Surveillance Program |journal=] |volume=40 |issue=7 |pages=885–92 |year=2002 |pmid=12507058 |doi= 10.1081/CLT-120016960|url=}}</ref><ref name="EPA1996">California EPA 1996, California Pesticide Illness Serveillance Program Report HS-1733 </ref> However, incident count does not take into account the number of people exposed and the severity of symptoms associated with each incident.<ref name="EPA1996"/> For example, if hospitalization were 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 ], none of the 515 pesticide-related hospitalizations recorded were attributed to glyphosate.<ref name="EPA1996"/>


In July 2019, the ]n parliament voted to ban glyphosate in Austria.<ref name=a-report-constitution-water-public>, Austrian parliament votes to forbid Glyphosphat & water is a public good necessary for the existence of a human, orf.at, 2019-07-02</ref>
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.<ref name=Giesy2000/> 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.<ref>{{cite journal |author=Daruich J, Zirulnik F, Gimenez MS |title=Effect of the herbicide glyphosate on enzymatic activity in pregnant rats and their fetuses |journal=Environmental Research |volume=85 |issue=3 |pages=226–31 |year=2001 |month=March |pmid=11237511 |doi=10.1006/enrs.2000.4229}}</ref> Also in recent mammalian research, glyphosate has been found to interfere with an enzyme involved testosterone production in mouse cell culture<ref name="walsh">{{cite journal |author=Walsh LP, McCormick C, Martin C, Stocco DM |title=Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (StAR) protein expression |url=http://jstor.org/stable/3434731 |journal=Environmental Health Perspectives |volume=108 |issue=8 |pages=769–76 |year=2000 |month=August |pmid=10964798 |pmc=1638308 |doi=10.2307/3434731}}</ref> and to interfere with an estrogen biosynthesis enzyme in cultures of human placental cells.<ref name="Aromatase">{{cite journal |doi=10.1289/ehp.7728 |author=Richard S, Moslemi S, Sipahutar H, Benachour N, Seralini GE |title=Differential effects of glyphosate and roundup on human placental cells and aromatase |journal=Environmental Health Perspectives |volume=113 |issue=6 |pages=716–20 |year=2005 |month=June |pmid=15929894 |pmc=1257596}}</ref>


In September 2019, the German Environment Ministry announced that the use of glyphosate will be banned from the end of 2023. The use of glyphosate-based herbicides will be reduced starting from 2020.<ref>{{cite news |last1=Rinke |first1=Andreas |title=Germany to ban use of glyphosate from end of 2023 |url=https://www.reuters.com/article/us-germany-glyphosate/germany-to-ban-use-of-glyphosate-from-end-of-2023-sources-idUSKCN1VP0TY |work=]|date=September 4, 2019}}</ref>
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.<ref name="autogenerated1" />


The assessment process for an approval of glyphosate in the European Union will begin in December 2019. France, Hungary, the Netherlands and Sweden will jointly assess the application dossiers of the producers. The draft report of the assessment group will then be peer-reviewed by the EFSA before the current approval expires in December 2022.<ref>{{cite web |last1=European Commission |title=Glyphosate Current status of glyphosate in the EU |url=https://ec.europa.eu/food/plant/pesticides/glyphosate_en |access-date=October 29, 2019|date=July 12, 2017 }}</ref>
=== Other species ===
The direct toxicity of ''pure'' glyphosate to ] and ] is low.<ref>{{cite web |url=http://www.ipmofalaska.com/files/Glyphosate.html |title=pest control from ipmofalaska.com |work= |accessdate=}}</ref> {{Verify credibility|date=January 2009}} The acute oral toxicity of Roundup is > 5,000&nbsp;mg/kg in the rat.<ref></ref> 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.<ref></ref><ref>http://npic.orst.edu/factsheets/glyphogen.pdf</ref>


The date has since been pushed back, partially due to very high interest and input in the participation process, with the ] (EFSA) even calling it an “unprecedented number”.<ref>{{Cite web |date=10 May 2022 |title=Glyphosate: EFSA and ECHA update timelines for assessments |url=https://www.efsa.europa.eu/en/news/glyphosate-efsa-and-echa-update-timelines-assessments |access-date=28 May 2022 |website=European Food Safety Authority}}</ref> Because the EFSA has to review all these 2400 comments and almost 400 responses, the process is expected to take longer. The created document is under extra review by the specially formed Glyphosate Renewal Group (GRG) and the Assessment Group on Glyphosate (AGG), the panel consisting of the four mentioned member states. With their responses now being scheduled for September 2022, the consultations with member states are supposed to be held by the very end of 2022.<ref>{{Cite web |date=11 May 2022 |title=Glifosato: La EFSA pospone su evaluacion ante la avalancha de comentarios recibidos |url=https://www.agrodigital.com/2022/05/11/glifosato-la-efsa-pospone-su-evaluacion-ante-la-avalancha-de-comentarios-recibidos/ |access-date=28 May 2022 |website=Agrodigital}}</ref><ref>{{Cite web |last=Case |first=Philip |date=11 May 2022 |title=EU delays glyphosaterenewal decision until 2023 |url=https://www.fwi.co.uk/news/farm-policy/eu-delays-glyphosate-renewal-decision-until-2023 |access-date=28 May 2022 |website=Farmers Weekly}}</ref> This would allow to finish the final assessment by mid-2023 and pass it on to further legislature to decide.
A study published in 2010 proposes that commercial glyphosate can cause neural defects and craniofacial malformations in ]s (Xenopus laevi). The experiments used frog ] that were incubated with 1/5000 dilutions of the commercial glyphosate. The frog embryos suffered diminution of the body size, size alterations on the cephalic area compromising the brain, reduction of the eyes, alterations of the ] and ], alterations of the ] and deficiency of the ]. The authors suggest that glyphosate itself was responsible for the observed results because the injection of pure glyphosate produced similar results. The results suggest that previous negative results of clinical studies on the offspring of those exposed to glyphosate in agricultural fields may not be correct.<ref name=AndresCarrasco>{{cite journal|author=Alejandra Paganelli, Victoria Gnazzo, Helena Acosta, Silvia L. Lpez and Andrs E.Carrasco|title=Glyphosate-Based Herbicides Produce Teratogenic Effects on Vertebrates by Impairing Retinoic Acid Signaling|journal=]|format=abstract|volume=23|page=100809132507020|date=2010-08-09|pmid=20695457|doi=10.1021/tx1001749|url=http://pubs.acs.org/doi/full/10.1021/tx1001749}}</ref>


In November 2023, glyphosate received 10 year renewed authorization for use in the EU.<ref>{{Cite web |date=2023-11-16 |title=No qualified majority reached by Member States to renew or reject the approval of glyphosate |url=https://ec.europa.eu/commission/presscorner/detail/en/statement_23_5792 |access-date=2023-11-16 |website=European Commission |language=en}}</ref>
An ''in vitro'' study indicates that glyphosate formulations could harm ]s<ref>{{cite journal | author = JA Springett and RAJ Gray | title = Effect of repeated low doses of biocides on the earthworm ''Aporrectodea caliginosa'' in laboratory culture | journal = ] | volume = 24 | issue = 12 | pages = 1739–1744 | year = 1992 | doi = 10.1016/0038-0717(92)90180-6}}</ref> and beneficial ]s.<ref>{{cite journal | doi = 10.1007/BF02374636 | title = Results of the fifth joint pesticide testing programme carried out by the IOBC/WPRS-Working Group “Pesticides and beneficial organisms” | year = 1991 | author = Hassan, S. A. | journal = Entomophaga | volume = 36 | page = 55 | last2 = Bigler | first2 = F. | last3 = Bogenschütz | first3 = H. | last4 = Boller | first4 = E. | last5 = Brun | first5 = J. | last6 = Calis | first6 = J. N. M. | last7 = Chiverton | first7 = P. | last8 = Coremans-Pelseneer | first8 = J. | last9 = Duso | first9 = C.}}</ref> However, the reported effect of glyphosate on earthworms has been criticized.<ref name=Giesy2000>JP Giesy, KR Solomon, S Dobson (2000). "Ecotoxicological Risk Assessment for Roundup Herbicide". Reviews of Environmental Contamination and Toxicology 167: 35-120</ref> 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.<ref>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.</ref> Glyphosate can negatively affect nitrogen-fixing bacteria,<ref>{{cite journal | title = Effects of glyphosate on nitrogen fixation of free-living heterotrophic bacteria
| url = http://www3.interscience.wiley.com/journal/119834785/abstract | year = 1995 | journal = Letters in Applied Microbiology | pages = 349–352 | volume = 20
| issue = 6 | accessdate = 2009-04-15 | author = Santos A, Flores M. | doi = 10.1111/j.1472-765X.1995.tb01318.x }}</ref> and increase the susceptibility of plants to disease.<ref>{{cite journal | title = Herbicide effects on plant disease | url = http://www.ppi-ppic.org/ppiweb/BRAZIL.NSF/3a773b217d047cd185256c24000746e8/30ad5d7475e1dc98032571f400712b22/$FILE/Herbicide%20Effects%20on%20Plant%20Disease.pdf | year = 2007 | journal = Outlooks Pest Manag | pages = 36–40 | volume = 18 | accessdate = 2009-04-15 | author = Duke SO et al. | doi = 10.1564/18feb13}}</ref> A 2005 study concluded that certain amphibians may be at risk from glyphosate use.<ref>{{cite journal |first1=Bette |last1=Hileman |year=2005 |title=Common herbicide kills tadpoles |journal=Chemical & Engineering News |volume=83 |issue=15 |page=11}}</ref>


===Other countries===
Certain surfactants used in some glyphosate formulations have higher toxicity to ] and ]s, resulting in some formulations of glyphosate not being registered for use in aquatic applications.<ref>Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities", Monsanto Corporation Backgrounder </ref> Monsanto produces glyphosate products with alternative surfactants that are specifically formulated for aquatic use, for example "Biactive" and "AquaMaster".<ref>Aquatic Use of Glyphosate Herbicides in Australia, Monsanto Corporation Backgrounder </ref> According to Monsanto, "Conservation groups have chosen glyphosate formulations because of their effectiveness against most weeds as glyphosate has very low toxicity to wildlife".<ref></ref> Glyphosate is used with five different salts, but commercial formulations of it contain ]s, 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.<ref name="autogenerated1">{{cite journal |author=Bradberry SM, Proudfoot AT, Vale JA |title=Glyphosate poisoning |journal=Toxicological Reviews |volume=23 |issue=3 |pages=159–67 |year=2004 |pmid=15862083 |doi=10.2165/00139709-200423030-00003}}</ref>
In September 2013, the ] approved legislation to ban 53 agrochemicals, including glyphosate; the ban on glyphosate was set to begin in 2015.<ref>Staff, Centralamericadata.com. September 6, 2013 </ref><ref>Staff, Centralamericadata.com. November 27, 2013 </ref><ref>Legislative Assembly of El Salvador. November 26, 2013
{{Webarchive|url=https://web.archive.org/web/20150531075642/http://www.asamblea.gob.sv/noticias/archivo-de-noticias/analizan-observaciones-del-ejecutivo-al-decreto-que-contiene-la-prohibicion-de-53-agroquimicos-que-danan-la-salud |date=May 31, 2015 }} </ref>


In the ], the state of ] preempts local laws that attempt to ban glyphosate. In 2015 there was an attempt to pass legislation at the state level that would repeal that preemption.<ref name="Minnea-StPaul-glyph-res">{{cite web | first1=Robyn | last1=Moore | title=Herbicide a growing problem | website=] | publisher=] | date=2021-08-08 | url=http://www.presspubs.com/citizen/news/herbicide-a-growing-problem/article_09362c4a-e475-11e4-8a7b-7b5484fd9d09.html | access-date=2021-08-09}}</ref>
Glyphosate's effect on ] may be limited, because when glyphosate comes into contact with the soil, it rapidly binds to ] and is inactivated.<ref name="epa.gov"></ref><ref>{{cite journal | author = M.M. de Andréa, ''et al.'' | title = Influence of repeated applications of glyphosate on its persistence and soil bioactivity | journal = ] | volume = 38 | issue = 11 | pages = 1329–1335 | year = 2003 2003 | url = http://www.scielo.br/pdf/pab/v38n11/18929.pdf}}</ref> Unbound glyphosate is degraded by bacteria. Low activity because of binding to soil particles suggests that glyphosate's effects on ] are limited. Low glyphosate concentrations can be found in many creeks and rivers in U.S. and Europe.<ref>Cox C. Glyphosate (Roundup) J Pest Reform. 1998;18:3–17.</ref>


In May 2015, the ] banned the use and import of glyphosate, effective immediately.<ref>Staff, Colombo Page. May 22, 2015 {{Webarchive|url=https://web.archive.org/web/20150630213502/http://www.colombopage.com/archive_15B/May22_1432308620CH.php |date=June 30, 2015 }}</ref><ref>Sarina Locke for the Australian Broadcasting Corporation. Updated May 27, 2015 </ref> However, in May 2018 the Sri Lankan government decided to re-authorize its use in the plantation sector.<ref>{{cite web | title = Glyphosate ban lifted for tea, rubber industries: Navin | url = http://www.dailymirror.lk/article/Glyphosate-ban-lifted-for-tea-rubber-industries-Navin-149402.html | work = Daily Mirror | date = 2018-05-02 }}</ref>
The ],<ref name="epa.gov"/> the EC Health and Consumer Protection Directorate, and the UN ] 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.<ref>Peluso M, Munnia A, Bolognesi C, Parodi S. Environ Mol Mutagen. 1998 31:55-9 PMID 9464316</ref> The authors concluded that the damage was "''not related to the active ingredient, but to another component of the herbicide mixture''".


In May 2015, ] blocked importation on all new orders of glyphosate-based herbicides for a temporary suspension awaiting outcomes of research.<ref name=Bermuda1>{{cite news | title = Health Minister: importation of roundup weed spray suspended | url = http://www.todayinbermuda.com/news/health/item/1471-health-minister-importation-of-roundup-weed-spray-suspended | publisher = Bermuda Today | date = 11 May 2015 | archive-url = https://web.archive.org/web/20150602094518/http://www.todayinbermuda.com/news/health/item/1471-health-minister-importation-of-roundup-weed-spray-suspended | archive-date = June 2, 2015 | url-status = dead }}</ref>
Mammal research indicates oral intake of 1% glyphosate induces changes in liver enzyme activities in ] ]s and their ]es.<ref>{{cite journal |author=Daruich J, Zirulnik F, Gimenez MS |title=Effect of the herbicide glyphosate on enzymatic activity in pregnant rats and their fetuses |journal=] |volume=85 |issue=3 |pages=226–31 |year=2001 |month=March |pmid=11237511 |doi=10.1006/enrs.2000.4229 |url=}}</ref>


In May 2015, ] announced that it would stop using glyphosate by October 2015 in the destruction of illegal plantations of ], the raw ingredient for ]. Farmers have complained that the aerial fumigation has destroyed entire fields of ] and other legal produce.<ref name="BBCColumbia" />
=== Aquatic effects ===
Glyphosate is one of the pesticides that pose the greatest danger to amphibians.<ref>{{cite book|last1=Chivian|first1=Eric|last2=Bernstein|first2=Aaron|editor=Eric Chivian|title=Sustaining Life: How Human Health Depends on Biodiversity|year=2008|publisher=Oxford University Press, USA|isbn=978-0195175097|page=209|chapter=Threatened Groups of Organisms Valuable to Medicine}}</ref> ] and aquatic ] are more sensitive to Roundup than terrestrial organisms.<ref name=Giesy2000/> 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.<ref name="epa_reds"/><br />
The EU classifies Roundup as ''R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.''<ref name="autogenerated3">http://lscgw1.monsanto.com/esh/msdslib.nsf/2B20DAEB04E8631C0625689700650B45/$file/Roundup%20Ultra%203000-5059en-gb.pdf Roundup Material Safety Data sheet page 7, heading 16</ref>


In April 2019, ]'s Ministry of Agriculture and Rural Development banned the use of glyphosate throughout the country.<ref name=Vietnam>{{cite news | title = Việt Nam bans weed killer ingredient glyphosate | url = http://vietnamnews.vn/society/518568/viet-nam-bans-weed-killer-ingredient-glyphosate.html | publisher = Viet Nam News | date = 11 April 2019}}</ref>
Roundup is not registered for aquatic uses<ref>Monsanto Backgrounder 2005 Response to "The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities" </ref> and studies of its effects on amphibians indicate it is toxic to them.<ref>Rick A. Relyea 2005 The impact of insecticides and herbicides on the biodiversity and productivity of aquatic communities Ecological Applications 15:618–627</ref> Other glyphosate formulations that are registered for aquatic use have been found to have negligible adverse effects on sensitive amphibians.<ref>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</ref>


In August 2020, ] President ] announced that glyphosate will be gradually phased out of use in Mexico by late 2024.<ref>{{cite web |title=Mexico to phase out use of herbicide glyphosate |url=https://www.reuters.com/article/us-mexico-herbicide-idUSKCN25902N |website=Reuters |access-date=3 March 2021 |date=13 August 2020}}</ref>
=== Endocrine disruptor debate ===
''In vitro'' studies have shown glyphosate affects progesterone production in mammalian cells<ref>{{cite journal |author=Walsh LP, McCormick C, Martin C, Stocco DM |title=Roundup inhibits steroidogenesis by disrupting steroidogenic acute regulatory (StAR) protein expression |journal=] |volume=108 |issue=8 |pages=769–76 |year=2000 |month=August |pmid=10964798 |pmc=1638308 |doi= 10.2307/3434731|url=http://jstor.org/stable/3434731}}</ref> and can increase the mortality of placental cells.<ref name=Richard2005/> Whether these studies classify glyphosate as an ] is debated.


Thailand's National Hazardous Substances Committee decided to ban the use of glyphosate in October 2019<ref>Reuters (October 25, 2019). </ref> but reversed the decision in November 2019.<ref>{{cite news |title=Thailand reverses ban of chemicals use in pesticides |url=https://www.reuters.com/article/us-thailand-chemicals/thailand-reverses-ban-of-chemicals-use-in-pesticides-idUSKBN1Y1128 |access-date=12 December 2019 |work=Reuters |date=27 November 2019 |language=en}}</ref>
== Environmental degradation ==


After a court-ruling in 2018, glyphosate was temporarily banned in ]. This decision was later overturned, causing major criticism by the federal agency of health (]). This comes, as the latest evaluations declared glyphosate as noncarcinogenic. Since all carcinogenic agrichemicals are automatically banned in the country, this allowed the continuous use.<ref>{{Cite web |last=Spring |first=Jake |date=26 February 2019 |title=Brazil health officials find weed-killer glyphosate non-cancerous |url=https://www.reuters.com/article/us-brazil-agriculture-glyphosate-idUSKCN1QF1J1 |access-date=28 May 2022 |website=Reuters}}</ref>
When glyphosate comes into contact with the soil, it can be rapidly bound to soil particles and be inactivated.<ref name="epa_reds">US EPA Reregistration Eligibility Decision - Glyphosate - (EPA-738-F-93-011) 1993 </ref> Unbound glyphosate can be degraded by bacteria.<ref>Balthazor, Terry M and Laurence Hallas (1986) Glyphosate-degrading microorganisms in industrial waste treatment biosystems. Appl. Environ. Microbiol. 51:432-34.</ref> However, glyphosate has been shown to increase the infection rate of wheat by fusarium head blight in fields that have been treated with glyphosate.<ref name="autogenerated2"> "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.</ref>


In New Zealand, glyphosate is an approved herbicide for killing weeds,<ref name="mpi-nz" /> with the most popular brand being ].<ref name="mpi-nz">{{Cite web|url=https://www.mpi.govt.nz/food-safety-home/safe-levels-of-chemicals-in-food/fertilisers-pesticides-hormones-and-medicines-in-food/glyphosate-in-food/|title=Glyphosate in food &#124; MPI - Ministry for Primary Industries. A New Zealand Government Department.|first=Ministry for Primary|last=Industries|website=www.mpi.govt.nz|date=July 13, 2021 }}</ref><ref name="epa-nz">{{Cite web|url=https://www.epa.govt.nz/everyday-environment/gardening-products/glyphosate/|title=Glyphosate &#124; EPA|website=www.epa.govt.nz}}</ref> Genetically modified crops designed to resist glyphosate are absent in New Zealand.<ref name="mpi-nz" /> Crops applied with glyphosate must be regulated under the HSNO Act 1996 and ACVM Act 1997.<ref name="mpi-nz" /><ref name="govtepa-pdf-nz">{{cite web|url=https://www.epa.govt.nz/assets/Uploads/Documents/Hazardous-Substances/Glyphosate-call-for-information/Glyphosate-call-for-information-summary-report-may22.pdf |title=Glyphosate in Aotearoa New Zealand |date=11 May 2022 |last=New Zealand Government}}</ref> Legal status for glyphosate use in New Zealand is approved for commercial and personal use.<ref name="epa-nz" /> In 2021, exports of New Zealand honey were found to contain traces of glyphosate, causing some concern to Japanese importers.<ref name="honey-nz-shun">{{Cite web|url=https://www.rnz.co.nz/news/country/434807/japan-warns-it-will-block-nz-honey-shipments-if-glyphosate-limits-breached|title=Japan warns it will block NZ honey shipments if glyphosate limits breached|date=January 20, 2021|website=] }}</ref><ref name="honey-nz-shun2">{{Cite web|url=https://thespinoff.co.nz/business/01-06-2021/glyphosate-is-farmings-favourite-weed-killer-can-nz-learn-to-live-without-it|title=Glyphosate is farming's favourite weed killer. Can NZ learn to live without it?|first=Nick|last=Stringer|date=June 1, 2021|website=The Spinoff}}</ref>
In soils, half-lives vary from as little as 3 days at a site in Texas to 141 days at a site in Iowa.<ref name=autogenerated6></ref> In addition, the glyphosate metabolite aminomethylphosphonic acid has been shown to persist up to 2 years in Swedish forest soils.<ref>http://www.labmeeting.com/paper/18974220/torstensson-1989-influence-of-climatic-and-edaphic-factors-on-persistence-of-glyphosate-and-24-d-in-forest-soils</ref> Glyphosate absorption varies depending on the kind of soil.<ref>{{cite doi|10.1016/j.envpol.2009.04.004}}</ref>


==Legal cases==
== Resistance in weeds and microorganisms ==
{{See also|Monsanto legal cases#Roundup}}
The first documented cases of weed resistance to glyphosate were found in Australia, involving rigid ryegrass near Orange, New South Wales.<ref></ref> 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.<ref name="autogenerated5"></ref><ref name="autogenerated4"></ref> Farmers associations are now reporting 103 biotypes of weeds within 63 weed species with herbicide resistance.<ref name="autogenerated5" /><ref name="autogenerated4" /> This problem is likely to be exacerbated by the use of roundup-ready crops.<ref>http://www.chem.purdue.edu/courses/chm333/Roundup%20Article.pdf</ref>
===Lawsuits claiming liability for cancer===
Since 2018, in a number of court cases in the United States, plaintiffs have argued that their cancer was caused by exposure to glyphosate in glyphosate-based herbicides produced by Monsanto/Bayer. Defendant Bayer has paid out over $9.6 billion in judgements and settlements in these cases. Bayer has also won at least 10 cases, successfully arguing that their glyphosate-based herbicides were not responsible for the plaintiff's cancer.<ref name=bayer-wins>{{Cite web |date=December 23, 2023 |title=Bayer wins latest Roundup cancer trial, ending losing streak |url=https://www.reuters.com/legal/bayer-wins-latest-roundup-cancer-trial-ending-losing-streak-2023-12-23/ |website=Reuters}}</ref>


===Advertising controversies===
A report, published in November, 2009 , "Impacts of Genetically Engineered(GE) Crops on Pesticide Use in the United States: The First Thirteen Years using ] data shows that since 1996, U.S. farmers have applied 383 million more pounds of herbicides on GE crops including soybeans than they likely would have applied on non-GE varieties of these crops. The same report states that the rise in pounds per acre is associated with the replacement of older, higher risk herbicides with glyphosate. Forty-six percent of the total increase occurred in the last two years studied (2007 and 2008). The same report states that the report identifies the problem as an increase in herbicide-resistant-weeds.,<ref>http://www.ucsusa.org/food_and_agriculture/science_and_impacts/impacts_genetic_engineering/report-documents-pesticide.html</ref><ref>{{cite news| url=http://www.nytimes.com/2010/04/14/business/energy-environment/14crop.html?hp | work=The New York Times | title=Study Says Overuse Threatens Gains From Modified Crops | first=Andrew | last=Pollack | date=April 13, 2010}}</ref><ref>{{cite news| url=http://www.nytimes.com/2010/05/04/business/energy-environment/04weed.html?emc=eta1 | work=The New York Times | title=Farmers Cope With Roundup-Resistant Weeds | first1=William | last1=Neuman | first2=Andrew | last2=Pollack | date=May 3, 2010}}</ref><ref>{{cite news| url=http://www.nytimes.com/2010/05/13/opinion/lweb13weeds.html?emc=eta1 | work=The New York Times | title=Toxic Weed Control | date=May 12, 2010}}</ref><ref name="nytimes.com"/>
In 2016, a lawsuit was filed against ] in the ] of both ] and ] after trace amounts of glyphosate were found in ]. The lawsuit alleged that the claim of "100% natural" was ].<ref>{{Cite news| issn = 0362-4331| last = Strom| first = Stephanie| title = Quaker Oats' 100% Natural Claim Questioned in Lawsuit| work = The New York Times| access-date = 2018-08-13| date = 2017-12-21| url = https://www.nytimes.com/2016/05/02/business/quaker-oats-100-natural-claim-questioned-in-lawsuit.html}}</ref> That same year ] dropped the label "Made with 100% Natural Whole Grain Oats" from their ] ] after a lawsuit was filed that claimed the ]s contained trace amounts of glyphosate.<ref>{{Cite web| title = General Mills drops '100% Natural' on Nature Valley granola bars after lawsuit| work = USA Today| access-date = 2018-08-25| url = https://www.usatoday.com/story/money/nation-now/2018/08/24/general-mills-drops-100-percent-natural-nature-valley/1082709002/}}</ref>


===Trade dumping allegations===
== Legal cases ==
United States companies have cited trade issues with glyphosate being ] into western world market areas by Chinese companies, and a formal dispute was filed in 2010.<ref name="urlwww.usitc.gov">{{cite web | url = https://www.usitc.gov/trade_remedy/731_ad_701_cvd/investigations/2010/Glyphosate%20from%20China/Preliminary/conference_04-22-2010.pdf | title = In the Matter of: Glyphosate From China | date = 2010-04-22 | publisher = United States International Trade Commission }}</ref><ref>{{cite news |last1=Hoskins |first1=Tim |title=Glyphosate maker complains of Chinese dumping |url=https://agupdate.com/iowafarmertoday/news/state-and-regional/glyphosate-maker-complains-of-chinese-dumping/article_b260291c-1d8d-56a9-8fd3-d460c89c8565.html |access-date=29 December 2023 |publisher=Iowa Farmer Today |date=15 April 2010}}</ref>
=== False advertising ===
In 1996 Monsanto was accused of false and misleading advertising of glyphosate products, prompting a lawsuit by the New York State attorney general.<ref></ref>


== Misinformation campaigns ==
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.
Glyphosate has become a locus of campaigning and misinformation by anti-GMO activists because of its association with genetically-modified glyphosate-resistant crops.<ref name=bogey>{{cite web |publisher=] |first=Bellamy |last=Jann |title=Monsanto gets injunction against California's mandated cancer warning for glyphosate |date=20 July 2020 |url=https://sciencebasedmedicine.org/monsanto-gets-injunction-against-californias-mandated-cancer-warning-for-glyphosate/}}</ref>
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.<ref></ref>


The US politician ] has incorporated glyphosate into his ] rhetoric, falsely claiming that both glyphosate and vaccines may be contributing to the American ].<ref name=bogey/> ] has also falsely claimed that it may have a role in ] and in worsening ].<ref name=ss>{{cite web |publisher=] |vauthors=Gorski DH |title=Quoth RFK Jr.: Vaccines and glyphosate are responsible for the obesity epidemic! |date=24 February 2020 |url=https://sciencebasedmedicine.org/quoth-rfk-jr-vaccines-and-glyphosate-are-responsible-for-the-obesity-epidemic/}}</ref>
=== 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.<ref>(US EPA Communications and Public Affairs 1991 ''Note to correspondents'' Washington DC Mar 1)</ref><ref>(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)</ref><ref>(U.S. Congress. House of Representatives. Com. on Gov. Oper. 1984. ''Problems plague the EPA pesticide registration activities''. House Report 98-1147)</ref> In the first incident involving Industrial Biotest Laboratories (IBT), 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 ] from male rabbits".<ref>(U.S. EPA 1978 Data validation. Memo from K Locke, Toxicology Branch, to R Taylor, Registration Branch. Washington DC Aug 9)</ref><ref>(U.S. EPA Office of pesticides and Toxic Substances 1983, ''Summary of the IBT review program''. Washington D.C. July)</ref><ref>Schneider, K. 1983. Faking it: The case against Industrial Bio-Test Laboratories. The Amicus Journal (Spring):14-26. Reproduced at </ref> 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.<ref>(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)</ref><ref>(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)</ref> Craven laboratories performed studies for 262 pesticide companies, including Monsanto.


==See also==
Monsanto has stated that the studies have been repeated, and Roundup's EPA certification does not now use any studies from Craven Labs or IBT. Monsanto alleges that the Craven Labs investigation was started by the EPA after a pesticide industry task force discovered irregularities.<ref>Backgrounder: Testing Fraud: IBT and Craven Labs, June 2005, Monsanto background paper on RoundUp </ref>
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== References == ==References==
{{Reflist|2}} {{Reflist}}
* EU (2002). . Retrieved October 28, 2005.
* {{cite journal | author=KR Solomon, DG Thompson |title=Ecological risk assessment for aquatic organisms from over-water uses of glyphosate | journal=Journal of Toxicology and Environmental Health | year=2003 | volume=6 | pages=289–324 |doi=10.1080/10937400306468 | pmid=12746143 | issue=3}}
* ], (1994).
* ].


==External links==
== Further reading ==
* Baccara, Mariagiovanna, et al. , 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


{{Commons category}}
== External links ==
* {{PPDB|373|Name=Glyphosate}}
{{Commons category|Glyphosates}}
* {{PPDB|1062|Name=Glyphosate trimesium}}
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