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Herbicides

Current Location: Home > Products > Herbicides

Glyphosate

HRAC G WSSA 9 For a general review, see Glyphosate. For glyphosate-trimesium, see Superseded Entries. glycine derivative

NOMENCLATURE
glyphosate
Common name glyphosate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA, JMAF) IUPAC name N-(phosphonomethyl)glycine
Chemical Abstracts name N-(phosphonomethyl)glycine Other names sulfosate* (for discontinued dimethylsulfonium salt) CAS RN [1071–83–6] EC no. 213–997–4 Development codes MON-0573 (Monsanto); CP 67573 (Monsanto) Smiles code OC(=O)CNCP(=O)(O)O
glyphosate-ammonium
CAS RN [40465–66–5] monoammonium salt; [114370–14–8] mono- or di- ammonium salt (unspecified) Development codes MON 8750 (Monsanto)
glyphosate-diammonium
CAS RN [69254–40–6]; [114370–14–8] mono- or di- ammonium salt (unspecified)
glyphosate-dimethylammonium
CAS RN [34494–04–7]
glyphosate-isopropylammonium
CAS RN [38641–94–0] EC no. 254–056–8 Development codes MON 0139 (Monsanto); MON 77209 (Monsanto)
glyphosate-potassium
CAS RN [39600–42–5] monopotassium salt; [70901–12–1] unspecified potassium salt
glyphosate-sesquisodium
CAS RN [70393–85–0], formerly [68822–12–8]; [34494–03–6] monosodium salt Development codes MON 8000; MON 8722 for glyphosate-sodium (both Monsanto)
PHYSICAL CHEMISTRY
Composition Tech. is ≥95% pure. Zwitterion structure (P. Knuuttila & H. Knuuttila, Acta Chem. Scand., 1979, 33, 623). Mol. wt. 169.1 M.f. C3H8NO5P Form Odourless, white crystals. M.p. 189.5 °C V.p. 1.31 × 10-2 mPa (25 °C) Kow logP <–3.2 (pH 5–9, 20 °C) (OECD 107; EEC A8) Henry <2.1 × 10-7 Pa m3 mol-1 (calc.) S.g./density 1.704 (20 °C) Solubility In water 10.5 g/l (pH 1.9, 20 °C). in acetone 0.078, dichloromethane 0.233, ethyl acetate 0.012, methanol 0.231, propan-2-ol 0.02 and toluene 0.036 g/l (20 °C). The alkali-metal and amine salts are readily soluble in water. Stability Glyphosate and all its salts are non-volatile, do not photochemically degrade in buffered water and are stable in air. Glyphosate is stable to hydrolysis at pH 3, 6 and 9 (5–35 °C). pKa 2.34 (20 °C), 5.73 (20 °C), 10.2 (25 °C) F.p. Not flammable
glyphosate-ammonium
Composition Tech. is 95.2% pure. Mol. wt. 186.1 M.f. C3H11N2O5P Form Odourless, white powder. M.p. Decomp. >190 °C, without melting V.p. 9 × 10-3 mPa (25 °C) Kow logP <–3.7 (20 °C). Henry 1.16 × 10-8 Pa m3 mol-1 (calc.) S.g./density 1.433 (22 °C) Solubility In water 144±19 g/l (pH 3.2). Essentially insoluble in organic solvents. In acetone 2.3, methanol 159 mg/l (20 °C). Stability Stable over 5 days at 50 °C (pH 4, 7 and 9). pKa 5.50 (20 °C) F.p. Not flammable
glyphosate-diammonium
Mol. wt. 203.1 M.f. C3H14N3O5P
glyphosate-dimethylammonium
Mol. wt. 214.2 M.f. C5H15N2O5P
glyphosate-isopropylammonium
Composition As a wet cake, contains c. 62% w/w isopropylammonium salt, c. 35% water. Mol. wt. 228.2 M.f. C6H17N2O5P Form Odourless, white powder. M.p. Occurs in 2 steps, 143–164 °C and 189–223 °C B.p. Decomposes without boiling V.p. 2.1 × 10-3 mPa (25 °C) Kow logP = –5.4 (20 °C) Henry 4.6 × 10-10 Pa m3 mol-1 (25 °C, calc.) S.g./density 1.482 (20 °C) Solubility In water 1050 g/l (25 °C, pH 4.3). In ethyl acetate 0.04 mg/l, heptanes 0.04 mg/l, methanol 15.7-28.4 g/l (all at 20 °C). Stability Stable 5 days at pH 4, 5 and 9 (50 °C). pKa 5.77±0.03, 2.18±0.02 (20±2 °C) (OECD 112)
glyphosate-potassium
Composition In products described as containing glyphosate-potassium, the CAS Registry Number for the salt with unspecified potassium content is usually quoted. Mol. wt. 207.2 (monopotassium salt) M.f. C3H7KNO5P (monopotassium salt) M.p. 219.8 °C Kow logP = <-4.0 (20°C) Henry 3.38 × 10-7 Pa m3 mol-1 (20 °C, calc.) Solubility In water 918.7 g/l (pH 7, 20 °C), Methanol 217 mg/l (20 °C). pKa 5.70 (20 °C)
glyphosate-sesquisodium
Mol. wt. 405.2; 191.1 glyphosate-sodium M.f. C6H14N2Na3O10P2; C3H7NNaO5P (glyphosate-sodium) Form Odourless, white powder. M.p. Decomp. >260 °C V.p. 7.56 × 10-3 mPa (25 °C) Kow logP = –4.58 (tech., 25 °C) Henry 4.27 × 10-9 Pa m3 mol-1 (glyphosate-sodium, calc.) S.g./density 1.622 (20 °C) (glyphosate-sodium) Solubility In water 335±31.5 g glyphosate-sodium/l of solution (or 414±51.8 g glyphosate-sodium/l of water) (pH 4.2, 20 °C). Stability Stable over 5 days (pH 4, 7 and 9, 50 °C).
COMMERCIALISATION
History Herbicidal activity reported by D. D. Baird et al. (Proc. North Cent. Weed Control Conf., 1971, 26, 64). The isopropylammonium, sodium and ammonium salts introduced by Monsanto Co. in 1974. The trimesium salt (q.v., in Supplementary Entries) introduced in 1989; the potassium salt introduced in 2002. The diammonium salt introduced by Syngenta AG. Patents US 3799758 (to Monsanto); EP 53871; US 4315765 (both to ICI) Manufacturers Monsanto; ACA; Agrochem; AgroDragon; Ancom; Anhui Huaxing; Anpon; Aragro; Atanor; Baocheng; Binnong; CAC; Cheminova; Chongqing Shuangfeng; Comlets; Dow AgroSciences; Drexel; Excel Crop Care; Feinchemie Schwebda; Fertiagro; Guangxin Agrochemical; Hebei Golhil; Herbex; High Kite; Hubei Sanonda; Hui Kwang; Huifeng Agrochemical; Iprochem; Jiangsu Good Harvest; Jiangsu Kuaida; Jiangsu Yangnong; Jinfanda; Jingma; KSA; Makhteshim-Agan; Nantong Jiangshan; Nortox; Nufarm China; Pyosa; Qingdao Kyx; Rainbow; Red Sun; Reposo; Sabero; Sannong; Sanonda Zhengzhou; Shandong Qiaochang; Shanghai Kaipu; Sharda; Sinon; Sundat; Xinan; Zhejiang Linghua
APPLICATIONS
Biochemistry Inhibits 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), an enzyme of the aromatic acid biosynthetic pathway. This prevents synthesis of essential aromatic amino acids needed for protein biosynthesis. Mode of action Non-selective systemic herbicide, absorbed by the foliage, with rapid translocation throughout the plant. Inactivated on contact with soil.
glyphosate
Uses Control of annual and perennial grasses and broad-leaved weeds, pre-harvest, in cereals, peas, beans, oilseed rape, flax and mustard, at c. 1.5–2 kg/ha; control of annual and perennial grasses and broad-leaved weeds in stubble and post-planting/pre-emergence of many crops; as a directed spray in vines and olives, at up to 4.3 kg/ha; in orchards, pasture, forestry and industrial weed control, at up to 4.3 kg/ha. As an aquatic herbicide, at c. 2 kg/ha. Formulation types SG; SL. Compatibility Mixing with other herbicides may reduce the activity of glyphosate.
glyphosate-sesquisodium
Uses A sugar cane ripener. Sodium salts, with unspecified stoichiometry, also used as a non-selective herbicide.
PRODUCTS
glyphosate
Selected products ‘Gladiator’ (Devidayal) ; ‘Glyfall’ (Hermoo) ; ‘Karda’ (Lainco) ; ‘Maxweed’ (Crop Health) ; ‘Nasa’ (Agria) ; ‘Pilarsato’ (Pilarquim) ; ‘Rinder’ (Inquiport) ; ‘Rophosate’ (Rotam) ; ‘Seccherba’ (Agrimix) ; ‘Sharp’ (Baocheng) mixtures ‘FlexstarGT’ (+ fomesafen-sodium) (Syngenta, Syngenta) ; ‘Folar’ (+ terbuthylazine) (Syngenta, Syngenta) ; ‘Halex GT’ (+ S-metolachlor + mesotrione) (Syngenta, Syngenta, Syngenta) Other products ‘AllOut’ (United Phosphorus) ; ‘Ancosate’ (Ancom) ; ‘Bounce’ (Zagro) ; ‘Brake’ (Biostadt) ; ‘CDA Vanquish’ (top fruit, etc.) (Bayer CropScience) ; ‘Control’ (Premier.Shukuroglou) ; ‘Crunch’ (Zagro) ; ‘Egret’ (United Agri) ; ‘Eversate’ (Zagro) ; ‘Fez’ (Zagro) ; ‘Fireball’ (Helena) ; ‘Galika’ (Efal) ; ‘Glialka’ (Agro-Chemie, Protex) ; ‘Glifene’ (Chimiberg) ; ‘Glifocas’ (CAS) ; ‘Glifogold’ (Agrimport) ; ‘Glifotox’ (Pyosa) ; ‘Glyagro’ (Agropharm) ; ‘Glyf’ (Chemia) ; ‘Glyfatex’ (Protex) ; ‘Glygran’ (Industria Prodotti) ; ‘Glyweed’ (Sabero) ; ‘Grassato’ (Hui Kwang) ; ‘Herbanil’ (Papaeconomou) ; ‘Herb Neat’ (Zagro) ; ‘Herphosate’ (Agrochem) ; ‘HM-2028’ (Helena) ; ‘Kawal’ (Zagro) ; ‘Krup’ (Krishi Rasayan) ; ‘Lafam’ (Agricultura Nacional) ; ‘Manah’ (Zagro) ; ‘Misa’ (Zagro) ; ‘Noweed’ (Dhanuka) ; ‘Perzocyd’ (Azot) ; ‘Pin Up’ (Zagro) ; ‘Pounce’ (Zagro) ; ‘Pounder’ (Zagro) ; ‘Powex’ (Zagro) ; ‘Punch’ (Zagro) ; ‘Rhizeup’ (Clayton) ; ‘Sarang’ (Zagro) ; ‘Selang’ (Zagro) ; ‘Silglif’ (Siapa) ; ‘Slash’ (Zagro) ; ‘Stacato’ (Sipcam S.p.A.) ; ‘Sunup’ (Sundat) ; ‘Sweep’ (United Phosphorus) ; ‘Tamrok’ (Phyteurop) ; ‘Tecoglif’ (Tecomag) ; ‘Total’ (AgroSan, Chemiplant) ; ‘Trinnashi’ (Hindustan) ; ‘Velox’ (Siapa) ; ‘Wipe Out’ (Zagro) ; ‘Wipe-Out CT Elite’ (Farmoz) ; ‘Resolva 24H’ (Syngenta) mixtures ‘Arimo’ (+ MCPA) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Butazin’ (+ terbuthylazine) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Clipper’ (France) (+ oryzalin + isoxaben) (Dow AgroSciences, Dow AgroSciences, Dow AgroSciences) ; ‘Coctel’ (+ MCPA) (Lainco, Lainco) ; ‘Fosmazina’ (+ simazine) (Probelte, Probelte) ; ‘Glifazin’ (+ terbuthylazine) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Glifo-Pop S’ (+ MCPA) (Agrimport, Agrimport) ; ‘Glisompa’ (+ MCPA) (Probelte, Probelte) ; ‘Pavanett’ (unspecified amine salts) (+ dichlorprop-P + MCPA) (Nufarm SAS, Nufarm SAS, Nufarm SAS) ; ‘Rondo-M’ (+ MCPA) (Crystal, Crystal) ; ‘Starmix’ (+ triclopyr) (Dow AgroSciences, Dow AgroSciences) ; ‘Topanex Ter’ (+ diuron + terbuthylazine) (Aragro, Aragro, Aragro) ; ‘Xanadu’ (+ diuron) (Bayer CropScience, Bayer CropScience) ; ‘Zapper’ (+ oxadiazon) (Bayer CropScience, Bayer CropScience) ; ‘Zoomer’ (+ oxyfluorfen) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Double Clutch SL’ (+ dicamba) (Syngenta, Syngenta) ; ‘Joso-Oh Showers’ (+ dicamba) (Syngenta, Syngenta) ; ‘Enlist Duo’ (+ 2,4-D) (Dow AgroSciences, Dow AgroSciences) Discontinued products ‘Alpha Glyphogan *’ (Makhteshim-Agan) ; ‘Arbex *’ (Crystal) ; ‘Banox *’ (Crystal) ; ‘Caoganlin *’ (Shenzhen Jiangshan) ; ‘CDA Spasor *’ (top fruit, etc.) (Aventis) ; ‘Chimarix *’ (Monsanto) ; ‘Clarion *’ (Zeneca) ; ‘Comet *’ (P I Industries) ; ‘Complete *’ (Stefes) ; ‘Fozzate *’ (Cedar) ; ‘Glennon *’ (Barclay) ; ‘Glider *’ (Portman) ; ‘GLY-480 *’ (Powaspray) ; ‘Glyper *’ (PBI) ; ‘Impulse *’ (unspecified sodium salt) (Monsanto) ; ‘Kickdown *’ (Stefes) ; ‘Nomix G *’ (Nomix-Chipman) ; ‘Nomix Nova *’ (Nomix-Chipman) ; ‘No-Weed *’ (Dow AgroSciences) ; ‘Poise *’ (Unicrop) ; ‘Stampede *’ (Zeneca) ; ‘Supex *’ (Crystal) ; ‘Swing *’ (unspecified sodium salt) (Monsanto) ; ‘Wipe-Out *’ (Farmoz) mixtures ‘Engame *’ (+ urea sulfate) (Arysta LifeScience, Arysta LifeScience) ; ‘Flier *’ (+ imazethapyr) (AGROFINA, AGROFINA) ; ‘Xanadu *’ (+ diuron) (Monsanto, Monsanto)
glyphosate-ammonium
Other products ‘Afdal’ (Ancom) ; ‘Amber’ (Ancom) ; ‘Ammo’ (Ancom) ; ‘Buggy Concentré Sprint’ (Phyteurop) ; ‘Mera 71’ (Excel Crop Care) ; ‘Rembat’ (Ancom) ; ‘Rival’ (Mexico) (Monsanto) ; ‘Rocket’ (China) (Monsanto) ; ‘Rondo Logico’ (Reposo) ; ‘Roundup Hi-Load’ (S Korea) (Monsanto) ; ‘SDF’ (Ancom) mixtures ‘Credit’ (+ glyphosate-isopropylammonium + glyphosate-isopropylammonium) (Nufarm Ltd, Nufarm Ltd, Nufarm UK, Nufarm UK) ; ‘Credit Duo’ (+ glyphosate-isopropylammonium) (Nufarm Americas, Nufarm Americas) ; ‘QuikPRO’ (+ diquat dibromide) (Monsanto, Monsanto) ; ‘Showdown’ (+ glyphosate-isopropylammonium) (Helena, Helena) ; ‘Trounce’ (+ metsulfuron-methyl) (Nufarm Ltd, Nufarm Ltd) ; ‘Weedmaster Duo’ (+ glyphosate-isopropylammonium) (Nufarm Ltd, Nufarm Ltd) Discontinued products ‘Kusatoban *’ (Monsanto) ; ‘Militia *’ (Monsanto) ; ‘Roundup PRODry *’ (Monsanto) ; ‘Roundup UltraDry *’ (Monsanto)
glyphosate-diammonium
Selected products ‘Touchdown’ (some Touchdown products contain glyphosate-potassium) (Syngenta) Other products ‘Fosato’ (Monsanto) ; ‘Polado II’ (Argentina) (Monsanto) ; ‘Touchdown CF’ (Syngenta)
glyphosate-dimethylammonium
Other products ‘Accord XRT II’ (Dow AgroSciences) ; ‘Duramax’ (Dow AgroSciences) ; ‘Durango DMA’ (Dow AgroSciences)
glyphosate-isopropylammonium
Selected products ‘Asset’ (Ancom) ; ‘Cosmic’ (Arysta LifeScience EAME) ; ‘Fozat’ (Agro-Chemie) ; ‘Gallup’ (Barclay) ; ‘Glycel’ (Excel Crop Care) ; ‘Glyfos’ (Cheminova) ; ‘Glyphogan’ (Makhteshim-Agan) ; ‘Glyphomax’ (Dow AgroSciences) ; ‘Glyphotox’ (Aimco) ; ‘Glysate’ (Mobedco) ; ‘Ground-Up’ (Vapco) ; ‘Nufosate’ (Nufarm UK) ; ‘Oxalis’ (Arysta LifeScience EAME) ; ‘Rodeo’ (Dow AgroSciences) ; ‘Rondo’ (Reposo) ; ‘Roundup’ (Monsanto) ; ‘Sanos’ (Hubei Sanonda) ; ‘Vifosat’ (Vipesco) ; ‘Yerbimat’ (Ingeniería Industrial) mixtures ‘PrePass’ (+ florasulam) (Dow AgroSciences, Dow AgroSciences) ; ‘Touchdown B-Power’ (+ butafenacil) (Syngenta, Syngenta) ; ‘Thunderbolt 007’ (non-selective herbicide) (+ pyraflufen-ethyl) (Nihon Nohyaku, Nihon Nohyaku) Other products ‘Accord’ (Dow AgroSciences) ; ‘Akira’ (Ancom) ; ‘Amega’ (Nufarm SAS) ; ‘Amiphosate’ (Agrolex) ; ‘Aqua Master’ (Monsanto) ; ‘Aquaneat’ (Nufarm Americas) ; ‘Aqua Neat’ (Nufarm Americas) ; ‘AquaPro’ (SePRO) ; ‘Aqua Star’ (Albaugh) ; ‘Arrow’ (Phyteurop) ; ‘Asteroid’ (Headland) ; ‘Atila’ (Afrasa) ; ‘Azural’ (Monsanto) ; ‘Barbarian’ (Barclay) ; ‘Boxer’ (Doğal) ; ‘Buggy’ (Sipcam S.p.A.) ; ‘Buggy Plus’ (Phyteurop) ; ‘Buggy Prim’ (Phyteurop) ; ‘Buggy Upper’ (Phyteurop) ; ‘Bypass’ (Dow AgroSciences) ; ‘Catamaran’ (Logofit) ; ‘Clean Up’ (Indofil) ; ‘Clear out’ (Chemical Products) ; ‘Clinic’ (Nufarm Deutschland, Nufarm España, Nufarm GmbH, Nufarm SAS, Nufarm UK) ; ‘Cornerstone’ (Winfield Solutions) ; ‘Credit Extra’ (Nufarm Americas) ; ‘Credit Systemic’ (Nufarm Americas) ; ‘Discman Biograde’ (Barclay) ; ‘Dominator’ (Dow AgroSciences) ; ‘Durango’ (Dow AgroSciences) ; ‘EH-1385’ (PBI/Gordon) ; ‘Envision’ (Headland) ; ‘Erase’ (Dow AgroSciences) ; ‘Exert’ (Ancom) ; ‘Extra Credit’ (Nufarm Americas) ; ‘Figaro’ (Logofit) ; ‘Flame’ (Interfarm) ; ‘Foresters’ (Nufarm Americas) ; ‘Forest Star’ (Albaugh) ; ‘Garryo’ (Barclay) ; ‘Gland-Up’ (Vapco) ; ‘Glifae’ (Cequisa) ; ‘Glifobel’ (Phyteurop) ; ‘Glifonox’ (Crystal) ; ‘Glifos’ (Cheminova) ; ‘Gliluq’ (LUQSA) ; ‘Glion’ (Milenia) ; ‘Glistar’ (ICN Hungary) ; ‘Glyfocal’ (Arysta LifeScience EAME) ; ‘Glyphader’ (Dow AgroSciences) ; ‘Glyphocal’ (Arysta LifeScience EAME) ; ‘Glyphomate’ (PBI/Gordon) ; ‘Glyphoroc’ (Logofit) ; ‘Glyphosan’ (Dow AgroSciences) ; ‘Glypro’ (Dow AgroSciences) ; ‘Glysate’ (Mobedco, Chemvet) ; ‘GlyStar’ (Albaugh) ; ‘Glytex’ (Vapco) ; ‘GP’ (Ancom) ; ‘Helosate’ (Helm Agro) ; ‘Herbocor’ (Herbos) ; ‘Herbolex’ (Aragro) ; ‘Hilite’ (Nomix Enviro) ; ‘Honcho’ (Monsanto) ; ‘Hopper’ (Dow AgroSciences) ; ‘Hoss Ultra’ (Helena) ; ‘Imitator’ (Drexel) ; ‘Jornal’ (Lucava) ; ‘Kalach’ (Arysta LifeScience EAME) ; ‘Kick-off’ (Dow AgroSciences) ; ‘KleenUp’ (Loveland, UAP) ; ‘Klinic’ (Nufarm Ltd) ; ‘Knock-Out’ (Hektaş) ; ‘Lancer’ (Nufarm SAS) ; ‘Lentosate’ (Nufarm Ltd) ; ‘Mad Dog’ (Agsco) ; ‘Madrigal’ (Logofit) ; ‘Makaze’ (Loveland, UAP) ; ‘Mamba’ (Dow AgroSciences) ; ‘Manifest’ (Headland) ; ‘Montana’ (Sapec) ; ‘Nitro Roc’ (Logofit) ; ‘Piton’ (Dow AgroSciences) ; ‘Polado L’ (Monsanto) ; ‘Poliglif’ (Dow AgroSciences) ; ‘Power’ (Monsanto) ; ‘Ranger’ (Monsanto) ; ‘Rascal’ (Winfield Solutions) ; ‘Rattler’ (Helena) ; ‘Razor’ (Nufarm Americas) ; ‘Roundup Original II’ (Monsanto) ; ‘Roundup Pro’ (Monsanto) ; ‘Roundup Ultra’ (Monsanto) ; ‘Roundup UltraMAX’ (Argentina) (Monsanto) ; ‘Rumbo’ (IQV) ; ‘Setter’ (Dow AgroSciences) ; ‘Shield’ (Ancom) ; ‘Solado Gold’ (Monsanto) ; ‘Spark’ (Monsanto) ; ‘Spasor’ (Monsanto) ; ‘Stern’ (Logofit) ; ‘Sting’ (Monsanto) ; ‘Stirrup’ (Nomix Enviro) ; ‘Supresate’ (Ancom) ; ‘Syabas’ (Ancom) ; ‘Taifun’ (Feinchemie Schwebda) ; ‘Tender’ (Monsanto) ; ‘Trop’ (Milenia) ; ‘Typhon’ (Feinchemie Schwebda) ; ‘Typhoon’ (Feinchemie Schwebda) ; ‘Vantage’ (Dow AgroSciences) ; ‘Verdys EV’ (Dow AgroSciences) ; ‘Vinash’ (Sulphur Mills) ; ‘Vival’ (Logofit) ; ‘Weedwallop’ (Nufarm UK) ; ‘Zap It’ (Athea) mixtures ‘Alteza’ (+ imazethapyr) (BASF, BASF) ; ‘Amitril’ (+ amitrole) (Nufarm España, Nufarm España) ; ‘Amok’ (+ diuron) (Cerexagri SA, Cerexagri SA) ; ‘Arsenal Xpress’ (+ imazapyr-isopropylammonium) (Nufarm Ltd, Nufarm Ltd) ; ‘Athado Super’ (+ terbuthylazine) (Probelte, Probelte) ; ‘Backdraft’ (+ imazaquin) (BASF, BASF) ; ‘CoStarr’ (+ dicamba-isopropylammonium) (Albaugh, Albaugh) ; ‘Cottonex PG’ (+ prometryn + fluometuron) (Makhteshim-Agan, Makhteshim-Agan, Makhteshim-Agan) ; ‘Credit’ (+ glyphosate-ammonium + glyphosate-ammonium) (Nufarm Ltd, Nufarm Ltd, Nufarm UK, Nufarm UK) ; ‘Credit Duo’ (+ glyphosate-ammonium) (Nufarm Americas, Nufarm Americas) ; ‘Eclipse’ (+ clopyralid-olamine (clopyralid-2-hydroxyethylammonium)) (Dow AgroSciences, Dow AgroSciences) ; ‘Evo’ (+ 2,4-D-isopropylammonium) (Ancom, Ancom) ; ‘Extreme’ (+ imazethapyr) (BASF, BASF) ; ‘Fallow Star’ (+ dicamba-isopropylammonium) (Albaugh, Albaugh) ; ‘Field Master’ (+ acetochlor + atrazine) (Monsanto, Monsanto, Monsanto) ; ‘Fusta’ (+ MCPA-isopropylammonium) (Monsanto, Monsanto) ; ‘Galaxia’ (+ MCPA-isopropylammonium) (Afrasa, Afrasa) ; ‘Galigan Slapshot’ (+ oxyfluorfen) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Glidus’ (+ diuron) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Glitz’ (+ terbuthylazine) (Sapec, Sapec) ; ‘Glykamba’ (+ dicamba) (Nufarm Americas, Nufarm Americas) ; ‘Glymix’ (+ 2,4-D-isopropylammonium) (Dow AgroSciences, Dow AgroSciences) ; ‘Hat-Trick’ (+ 2,4-D-isopropylammonium) (Ancom, Ancom) ; ‘Herbamide’ (MCPA as unspecified amine salt) (+ MCPA + diuron) (Nufarm SAS, Nufarm SAS, Nufarm SAS) ; ‘Illico’ (+ amitrole) (Nufarm Ltd, Nufarm Ltd) ; ‘Jardiflow’ (MCPA as unspecified amine salt) (+ diuron + MCPA) (Nufarm SAS, Nufarm SAS, Nufarm SAS) ; ‘Kontraktor’ (+ 2,4-D-isopropylammonium) (Ancom, Ancom) ; ‘Landmaster’ (+ 2,4-D-isopropylammonium) (Monsanto, Monsanto) ; ‘Laser Plus’ (+ oxyfluorfen) (Afrasa, Afrasa) ; ‘Montana Trio’ (+ terbuthylazine + linuron) (Sapec, Sapec, Sapec) ; ‘One Shot’ (+ imazaquin-ammonium) (BASF, BASF) ; ‘Onestep’ (+ imazapyr-isopropylammonium) (BASF, BASF) ; ‘ProDeuce’ (+ prodiamine) (Nufarm Americas, Nufarm Americas) ; ‘Razor Burn’ (+ diquat dibromide) (Nufarm Americas, Nufarm Americas) ; ‘Recoil’ (+ 2,4-D) (Nufarm Americas, Nufarm Americas) ; ‘Rustler’ (Canada) (+ dicamba) (Monsanto, Monsanto) ; ‘Sable’ (+ MCPA) (Aragro, Aragro) ; ‘Samba’ (+ diuron) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Showdown’ (+ glyphosate-ammonium) (Helena, Helena) ; ‘Standout’ (+ imazethapyr) (BASF, BASF) ; ‘Staple Plus’ (+ pyrithiobac-sodium) (DuPont, DuPont) ; ‘Thunderbolt’ (+ pyraflufen-ethyl) (Nihon Nohyaku, Nihon Nohyaku) ; ‘Touché’ (+ diuron) (Nomix Enviro, Nomix Enviro) ; ‘Trevissimo’ (+ diuron) (Arysta LifeScience EAME, Arysta LifeScience EAME) ; ‘Ustinex G’ (+ diuron) (Bayer CropScience, Bayer CropScience) ; ‘Weedmaster Duo’ (+ glyphosate-ammonium) (Nufarm Ltd, Nufarm Ltd) Discontinued products ‘Apache *’ (Syngenta) ; ‘Dart *’ (Barclay) ; ‘Erranca *’ (Herbex) ; ‘Expedite II *’ (Monsanto) ; ‘Ezject *’ (Monsanto) ; ‘Forza *’ (Cheminova) ; ‘Garryowen *’ (Barclay) ; ‘Greenfix *’ (Luxan) ; ‘Jury *’ (Agriliance) ; ‘Kernel *’ (Cheminova) ; ‘MSS Glyfield *’ (Nufarm UK) ; ‘Naf522 *’ (Dow AgroSciences) ; ‘Pondmaster *’ (Monsanto) ; ‘Protocol *’ (Monsanto) ; ‘Smash *’ (Herbex) ; ‘Stride *’ (Syngenta) mixtures ‘A-11976E *’ (+ atrazine) (Syngenta, Syngenta) ; ‘Bronco *’ (+ alachlor) (Monsanto, Monsanto) ; ‘Campaign *’ (+ 2,4-D-isopropylammonium) (Monsanto, Monsanto) ; ‘Fallow Master *’ (+ dicamba-isopropylammonium) (Monsanto, Monsanto) ; ‘Hockey Pro *’ (+ diuron) (Monsanto, Monsanto) ; ‘Illico TR *’ (+ amitrole) (Nufarm SAS, Nufarm SAS) ; ‘Nomix TH 20 *’ (+ diuron) (Nomix-Chipman, Nomix-Chipman) ; ‘Oriflam *’ (+ amitrole) (Nufarm SAS, Nufarm SAS) ; ‘Ready Master ATZ *’ (+ atrazine) (Monsanto, Monsanto) ; ‘Rebin GT *’ (+ butafenacil) (Syngenta, Syngenta) ; ‘RT Master *’ (+ 2,4-D-isopropylammonium) (Monsanto, Monsanto) ; ‘Weemax *’ (+ amitrole) (Nufarm SAS, Nufarm SAS)
glyphosate-potassium
Other products ‘DupliKator’ (Drexel) ; ‘Roundup Original Max’ (Monsanto) ; ‘Roundup PowerMax’ (Monsanto) ; ‘Roundup ProMax’ (Monsanto) ; ‘Roundup Transorb’ (Monsanto) ; ‘Roundup WeatherMAX’ (Monsanto) ; ‘RT 3’ (Monsanto) ; ‘RT 540’ (Monsanto) ; ‘Touchdown CT’ (Syngenta) ; ‘Touchdown Hitech’ (Syngenta) ; ‘Touchdown Total’ (Syngenta) mixtures ‘Sequence’ (+ S-metolachlor) (Syngenta, Syngenta) Discontinued products ‘RT Master II *’ (Monsanto) mixtures ‘Mascot *’ (+ diuron + terbuthylazine) (Syngenta, Syngenta, Syngenta)
glyphosate-sesquisodium
Other products ‘Erase Granules’ (unspecified sodium salt) (Plaaskem S.A.) Discontinued products ‘Polado *’ (Monsanto)
ANALYSIS
Product analysis by hplc with uv detection (AOAC Methods, 18th Ed., 983.10; CIPAC Handbook, 1985, 1C, 2132; ibid., 1998, H, 182), or by ion-exchange lc with uv detection (AOAC Methods, 18th Ed., 996.12). Residues determined by gc with MSD (also applicable to aminomethylphosphonic acid, AOAC Methods, 18th Ed., 2000.05), by hplc with o-phthalaldehyde post-column reaction specific for primary amines (J. Agric. Food Chem., 1986, 34(6), 955–960), or by gc/FPD (Resid. Anal. Methods). See also Pestic. Anal. Man., II, 180.364. In water by hplc determination by o-phthalaldehyde post-column reaction system (AOAC Methods, 18th Ed., 991.08), by hplc/FLD (Environ. Chem. Methods), or by gc/FPD (ibid.). In soil by gc/FPD or gc/ms (ibid.).
ENVIRONMENTAL FATE
Animals In mammals, following oral administration, glyphosate is very rapidly excreted unchanged and does not bioaccumulate. Plants Slowly metabolised to aminomethylphosphonic acid ([1066–51–9]), which is the major plant metabolite. Soil/Environment In soil (field), DT50 1–130 d, depending on edaphic and climatic conditions. In water, DT50 varies from a few to 91 d. Photodegradation in natural water occurs, DT50 33–77 d; no substantial photodegradation in soil was recorded over 31 d. In a lab. whole system with water and sediment, DT50 27–146 d (aerobic), 14–22 d (anaerobic). The major metabolite in soil and water is aminomethylphosphonic acid.
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EHC 159 (1994). JMPR Mtg. 103 (2005); JMPR Evaln. I 72 (1994), 81 (1997), 105 (2005); JMPR Evaln. II 49 (1986), 104 (2004); JMPR Evaln. I 81 (1997); JMPR Evaln. II 82 (1997) (for degradation product aminomethylphosphonic acid). PDS 91 (1996). ICSC 0160 (2005); EU Rev. Rep. 6511/VI/99 (2002). EU Status (1107/2009) Approved, 2001/99/EC, expiry date extended 2010/77/EC.
MAMMALIAN TOXICOLOGY
glyphosate
Oral Acute oral LD50 for rats >5000, mice >10 000, goats 3530 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Eye irritant; non-irritating to skin (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >4.98 mg/l air. NOEL In 2 y feeding trials, no ill-effects were observed in rats receiving 410 mg/kg diet daily (ave.) and, in 1 y feeding trials, no ill-effects were observed in dogs receiving 500 mg/kg daily (highest dose treated). Lowest relevant NOAEL (2 y) for rats 31 mg/kg b.w. daily (EU). ADI (JMPR) 1 mg/kg b.w. [2004]; (EC) 0.3 mg/kg b.w. [2001]; (EPA) proposed RfD 2 mg/kg b.w. [1993]. Water GV GV not established (O). Other Not mutagenic, not carcinogenic, not teratogenic, not neurotoxic. No adverse effects on reproduction. Toxicity class WHO (a.i.) U EPA (formulation) III EC classification Xi; R41| N; R51, R53
glyphosate-ammonium
Oral Acute oral LD50 for rats 4613 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Slight eye irritant; not a skin irritant (rabbits). Inhalation LC50 for rats (whole body) >1.9 mg/l air. ADI See glyphosate. EPA (formulation) III EC classification N; R51, R53
glyphosate-diammonium
EC classification N; R51, R53
glyphosate-isopropylammonium
Oral Acute oral LD50 for rats >5000, goats 5700 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Slight eye irritant; not a skin irritant (rabbits). Inhalation LC50 (4 h) for rats >1.3 mg/l air. NOEL In a 6 mo capsule trial, no ill-effects were observed in dogs receiving 300 mg/kg daily (highest dose treated). ADI See glyphosate. EPA (formulation) III EC classification N; R51, R53
glyphosate-potassium
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Moderate eye irritant; not a skin irritant (rabbits). Inhalation LC50 (4 h) for rats >5.27 mg/l air. ADI See glyphosate. EPA (formulation) III EC classification N; R51, R53
glyphosate-sesquisodium
Skin and eye Acute oral LD50 for rats >5000 mg/kg. Slight eye irritant; not a skin irritant (rabbits). EPA (formulation) IV EC classification N; R51, R53
ECOTOXICOLOGY
glyphosate
Birds Acute oral LD50 for bobwhite quail >3851 mg/kg. Dietary LC50 (5 d) for quail and ducks >4640 mg/kg diet. Fish LC50 (96 h) for trout 86, bluegill sunfish 120, harlequin fish 168, sheepshead minnows >1000 mg/l. Daphnia LC50 (48 h) 780 mg/l. Algae EbC50 (72 h) for green algae (Selenastrum capricornutum) 485 mg/l, (7 d) 13.8 mg/l, ErC50 (72 h) 460 mg/l; EC50 (96 h) for marine algae (Skeletonema costatum) 1.3 mg/l, (7 d) 0.64 mg/l; EC50 (7 d) for diatom (Navicula pelliculosa) 42, blue-green algae (Anabaena flos-aquae) 15 mg/l. Other aquatic spp. LC50 (96 h) for mysid shrimps (Mysidopsis bahia) >1000, grass shrimps 281, fiddler crabs 934 mg/l. EC50 (96 h) for sea urchins >1000 mg/l; (14 d) for Lemna gibba 25.5 mg/l; (48 h) for Litoria moorei tadpoles 111 mg/l. Bees LD50 (48 h) (contact) >100 μg/bee; (oral) 100 μg/bee. Other beneficial spp. Formulation of glyphosate had no effects on carabid beetles; harmless to slightly harmful to green lacewing, parasite species, mites/spiders and insects, except moderately harmful to Bembidion lampros (EU Guidelines).
glyphosate-isopropylammonium
Fish LC50 (96 h) for trout and bluegill sunfish >1000, fathead minnows 97, channel catfish 130 mg/l. Daphnia LC50 (48 h) 930 mg/l. Algae EbC50 (72 h) for Scenedesmus subspicatus 72.9 mg/l, ErC50 (72 h) 166 mg/l. Other aquatic spp. EC50 (48 h) for midge larvae 5600, Litoria moorei tadpoles >343 mg/l. Worms LC50 (14 d) for earthworms (Eisenia foetida) >5000 mg/kg soil. Reproductive toxicity NOEC (56 d) 28.79 mg/kg.
glyphosate-potassium
Birds Acute oral LD50 for bobwhite quail >2241 mg a.e./kg. Fish LC50 (96 h) for trout >1227 mg a.e./l. Daphnia LC50 (48 h) >1227 mg a.e./l. Algae EbC50 (72 h) for green algae (Selenastrum capricornutum) 35 mg a.e./l, ErC50 (72 h) 54 mg a.e./l. Bees LD50 (48 h) (contact and oral) >100 g a.e./bee.

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