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  • Glyphosate
Name:Glyphosate
CAS No:1071-83-6

PRODUCT DESCRIPTION

【Name】
Glyphosate
【CAS Registry number】
1071-83-6
【Synonyms】
N-Phosphonomethyl-glycine
N-(phosphonomethyl)gtycine
Glyphosate aqueous solution (10%)
Glyphosate isopropyl amine salt aqueous solution(41%)
Glyphosate ammonium solution(10%)
Glyphosate S.P.
(Carboxymethylamino)methylphosphonic acid
Phosphonomethylaminoacetic acid
N-Phosphomethylglycine
Bronco
【EINECS(EC#)】
213-997-4
【Molecular Formula】
C3H8NO5P (Products with the same molecular formula)
【Molecular Weight】
169.07
【Inchi】
InChI=1/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)
【Canonical SMILES】
C(C(=O)O)NCP(=O)(O)O
【MOL File】
1071-83-6.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.74
【Melting Point】
230℃
【Boiling Point】
465.8 °C at 760 mmHg
【Refractive Index】
1.576
【Flash Point】
235.5 °C
【Water】
1.2 g/100 mL
【Solubilities】
1.2 g/100 mL in water
【Color/Form】
White solid
Colorless crystals
【Stability】
Stable. Incompatible with metals, strong oxidizing agents, strong bases. May be light sensitive.
【Storage temp】
APPROX 4°C
【Computed Properties】
Molecular Weight:169.073081 [g/mol]
Molecular Formula:C3H8NO5P
XLogP3-AA:-4.6
H-Bond Donor:4
H-Bond Acceptor:6
Rotatable Bond Count:4
Exact Mass:169.014009
MonoIsotopic Mass:169.014009
Topological Polar Surface Area:107
Heavy Atom Count:10
Formal Charge:0
Complexity:162
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:1
Feature 3D Anion Count:2
Feature 3D Cation Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:7

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R41;R51/53
【Safety Statements 】
S2;S26;S39;S61
【Skin, Eye, and Respiratory Irritations】
Glyphosate in the formulated product can cause eye and skin irritation. /Formulated herbicide/
Concentrated solutions /of glyphosate/ can cause dermal irritation.
Some glyphosate end-use products are in Toxicity Categories I or II form primary eye irritation or skin irritation. In California, glyphosate ranks high among pesticides causing illness or injury to workers, who report numerous incidents of eye and skin irritation from splashes during mixing and loading.
【Cleanup Methods】
Sweep spilled substance into plastic containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
Hydrolysis: Mix glyphosate with excess CaO /calcium oxide/ or NaOH /sodium hydroxide/ and sand or lye and sand or other adsorbent in a pit or trench at least 0.5 m deep in a clay soil. NaOH (or Na2CO3) /sodium carbonate/ can also be added to the mixture to help speed the reactions when CaO is used as the main alkali. The amt of CaO or NaOH to use depends on the amt of pesticide to be disposed of and, to some extent, the concentration of active ingredient in the pesticide and the actual chemical nature of the active ingredient. A practical guideline, in the absence of specific directions, is to use an approx volume or weight of alkali from one-half of to the same as that of the pesticide. For dilute formulations, such as a 1% soln or dust, the amount of CaO of NaOH can be reduced by one-half. For very concentrated pesticides (over 80% active ingredient) the amount of CaO or NaOH can be doubled, but the concentrate should be mixed first with water (or soapy water) before reaction with the alkali. For safety, a preliminary test should be made in which very small amt of the pesticide and alkali are mixed and observed briefly to make sure it does not react too vigorously. Sizable quantities of pesticides can be disposed of in several smaller batches, rather than all at once, for added safety. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
【Transport】
UN 3077 9/PG 3
【Fire Fighting Procedures】
/To fight fire use/ powder, alcohol-resistant foam, water spray, carbon dioxide.
【Formulations/Preparations】
Aqueous solution, water-soluble liquid, water soluble concentrate.
Polado (plant growth regulator), water soluble powder (750 g glyphosate-sesquisodium/kg) /Glyphosate sesquisodium/
... Technical grade glyphosate (averaging 96% purity on a dry weight basis).
Clearout TEC, 96.7% Glyphosate
Fozzate, 80% Glyphosate
Gly-Flo 96% Acid Technical, 96.3% Glyphosate
Glygran WDG, 80% Glyphosate
Glyphogan Herbicide, 41% Glyphosate
Glyphosate Technical, 88% glyphosate
Glyphosate Acid Technical Dry, 96% glyphosate
Kleeraway SYstemic Weed & Grass Killer2, 5% Glyphosate
Kull Tgai Glyphosate, 96.1% Glyphosate
RD1619 Herbicide, 71.4% Glyphosate
Recoil Broad Spectrum Herbicide, 11.38% 2-4,D; 23.03% Glyphosate
Roundup Dry Concentrate, 95.2% glyphosate
Standout Herbicide, 2.7% Imazethapyr, 21.9% Glyphosate
Touchdown 008, 0.6% Dicamba, 43.4% Glyphosate
Touchdown Diquat Home and Garden Concentrate, 0.73% Diquat dibromide, 13.4% glyphosate
Touchdown Herbicide, 28.3% Glyphosate
Touchdown Hitech Herbicide, 52.3% glyphosate
Touchdown Total, 36.5% glyphosate
【Other Preventative Measures】
Avoid contacting the skin or eyes with the undiluted substance ... Keep out of the reach of children. Prevent drifting over neighboring crops.
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Worker Protection Standard (WPS) Requirements. Any product whose labeling permits use in the production of an agricultural plant on any farm, forest, nursery or greenhouse must comply with the labeling requirements of: PR Notice 93-7, "Labeling Revisions Required by the Worker Protection Standard (WPS)," andPR Notice 93-11, "Supplemental Guidance for PR Notice 93-7." Unless specifically directed in the RED, all statements required by these two PR Notices must appear on product labeling exactly as instructed in the Notices. Labels /for glyphosate/ were required to/ be revised by April 21, 1994, for products distributed or sold by the primary registrant or supplementally registered distributors, and by October 23, 1995, for products distributed or sold by anyone.
/Glyphosate/ Products Not Primarily Intended for Home Use: Uses Within the Scope of the Worker Protection Standard (WPS) - A 12-hour restricted entry interval (REI) is required for all products with uses within the scope of the WPS, except products intended primarily for home use. The PPE for early entry should be that required for applicators of glyphosate, except any applicator requirement for an apron or respirator is waived. This REI and PPE should be inserted into the standardized statements required by PR Notice 93-7. Sole Active Ingredient End-Use Products - Labels must ... adopt the entry restrictions set forth in this section. ... Multiple Active Ingredient Products - ... A specific time period in hours or days is considered more protective than "until sprays have dried" or "dusts have settled."
【Protective Equipment and Clothing】
Glyphosate in the formulated product can cause eye and skin irritation. /Formulated herbicide/
Concentrated solutions /of glyphosate/ can cause dermal irritation.
Some glyphosate end-use products are in Toxicity Categories I or II form primary eye irritation or skin irritation. In California, glyphosate ranks high among pesticides causing illness or injury to workers, who report numerous incidents of eye and skin irritation from splashes during mixing and loading.
【Octanol/Water Partition Coefficient】
log Kow = -3.40
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Waste streams were subjected to biol treatments following lime-pretreatment to reduce amt of glyphosate. Glyphosate itself showed only partial reduction with biol treatment.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

J. E. Franz, DE patent 2152826; idem, US patent 3799758 and US patent 3853530 (1972, 1974, 1974 all to Monsanto).
The classical synthesis starts with iminodiacetic acid, phosphorous trichloride and formaldehyde, but also sequences using glycine and dimethyl phosphate have been applied.
【Usage】

Non-selective, non-residual post-emergence herbicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
- Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
- Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes.
【Biomedical Effects and Toxicity】
The disposition of glyphosate was studied in rats. Male F344/N rats were gavaged with 5.6 or 56 mg/kg radiolabeled glyphosate. Urine and feces were collected at 24 hour intervals for 72 hr and analyzed for activity. Selected rats were killed 3 to 96 hr post dosing to determine the tissue distribution of radioactivity. Approximately 20 to 30% of either dose was eliminated in the urine and 70 to 80% in the feces over 72 hr. Only about 1% of the dose remained in the tissues, mostly in the liver and small intestine.
... There is rapid elimination, no biotransformation, and minimal tissue retention of glyphosate in various species, including mammals, birds, and fish.
Greater than 90% of an orally administered dose of glyphosate is rapidly eliminated in 72 hr /by laboratory animals/. ... Typically, approximately 70% of the administered dose is eliminated in the feces, with the remainder eliminated in the urine. In all cases, less than 0.5% of the administered dose is found in the tissue and organs, demonstrating that glyphosate does not bioaccumulate in edible tissues.
Rats orally dosed with 14C-labeled glyphosate acid in water absorbed 20-30% and excreted the remainder in the feces. A 10-fold higher dose resulted in 30-fold higher blood concentrations, suggesting an enhanced absorption ratio at higher doses. Pretreatment of rats with surfactant and glyphosate in drinking water did not increase the subsequent absorption of the labeled glyphosate.
Dermal absorption has been determined experimentally in an in vitro human skin model using 14C-labeled glyphosate in formulated herbicide. After 16 hours, not more than 2.3% of the applied dose was recovered in the plasma receptor fluid. In vivo dermal absorption studies in rhesus monkeys confirmed poor absorption; total urinary recovery of labeled glyphosate was only 0.4% of applied dose in 24 hours and 2% in 7 days. Water or soap and water washing removed the applied glyphosate; 50% was still recoverable by washing at 24 hours. Several worker-biomonitoring studies verify poor dermal absorption by failing to find detectable levels of glyphosate in the urine. /Glyphosate herbicide formulations/
Following IV dosing of labeled glyphosate in rats, 90% was recovered in urine in 6 hours, and essentially all within 24 hours. IV dosing of glyphosate in dogs resulted in a /volume of distribution/ of 0.28 L/kg, and average elimination half-life of 82 minutes, and a renal clearance of 2.5 + or - 0.5 mL/min/kg.
Single or repeated doses of radiolabeled 14C-glyphosate were administered orally to male and female Sprague-Dawley rats. Following a single oral dose of 14C-glyphosate, 30 to 36% of the dose was absorbed, less than 0.27% of the dose was eliminated as CO2 /and 97.5%/ of the administered dose was excreted in the urine and feces as the parent compound, glyphosate. ... Less than 1.0% of the absorbed dose remained in tissues and organs, primarily in bone tissue. Repeated dosing at 10 mg/kg did not significantly change the metabolism, distribution or excretion of glyphosate.
Male and female Sprague-Dawley rats received single intraperitoneal injections of radiolabeled 14C-glyphosate. The dose level of glyphosate used for male and female rats was 1150 mg/kg. Blood samples were collected 0.25, 0.50, 1, 2, 4, 6 and 10 hours after injection. Femoral bone marrow samples were collected from one third of the male and female rats sacrificed at 0.5, 4, or 10 hours after injection. Thirty minutes after injection of glyphosate, the concentration of radioactivity in the bone marrow of male and female rats was equivalent to 0.0044% and 0.0072%, respectively, of the administered dose. These findings indicate that very little glyphosate reaches bone marrow, that it is rapidly eliminated from bone marrow and that it is even more rapidly eliminated from plasma.
In a 14-day oral study in rats with application of 14C-glyphosate via the diet (dose levels 1, 10 and 100 mg/kg feed), the observed total excretion in urine was 
Pretreatment with unlabelled compound for 14 days /to rats/ (carried out at the low dose level; /10 mg/kg/bw/) did not have an effect on whole body elimination. Seven days after dosing, 
In the period of 0-5 days after a single oral application of 14C-glyphosate (6.7 mg/kg body weight) to rats the total excretion in urine was 15% (males) and 35-43% (females) of the administered dose; total excretion in feces was 85% (males) or 50-55% (females). Less than 1% of the radiolabel was expired as 14CO2. In a more recent study, the very low level of expiration as 14CO2 was confirmed but no significant inter-sex difference in the level of 14C in excreta was observed. The result of the latter study was that at both oral dose levels (10 and 1000 mg/kg body weight) elimination in feces was 62-70% and excretion in urine was 14-18% (1000 mg/kg body weight) or 22-29% (10 mg/kg body weight); less than 0.2% of the dose was expired as 14CO2.
In rabbits > 80% was eliminated in feces (with additional 14C present in the gut) and 7-11% in urine within 5 days after administration of a single oral dose (6.7 mg/kg body weight) of 14C-glyphosate. Less than 1% of the dose was expired as 14CO2. In one oral study in lactating goats lasting 5 days, total excretion in urine varied from 20 to 24% and in feces from 60 to 66%.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2,600 to 4,900(2), indicate that glyphosate is expected to have slight mobility in soil(SRC). Volatilization of glyphosate from moist soil surfaces is not expected to be an important fate process because it exists in zwitterionic form in the environment and ionic compounds do not volatilize(3). Glyphosate is not expected to volatilize from dry soil surfaces based on a vapor pressure of 9.8X10-8 mm Hg(4). The biodegradation half-life of glyphosate in a Kickapoo sandy loam and Dupo silt loam soil were 1.85 and 2.06 days, respectively under aerobic conditions(5).
TERRESTRIAL FATE: After 16 wk, 
TERRESTRIAL FATE: Would not be expected to persist from one growing season to the next.
TERRESTRIAL FATE: Half-life in soil is normally less than 60 days.
TERRESTRIAL FATE: After glyphosate is applied to forests, fields, and other land by spraying, its mobility in soil is limited and is affected by pH and phosphate levels, as well as by soil type(3). In addition to binding to organic matter and clay in soil, it may also form insoluble complexes with metal ions in the soil. Distribution data for glyphosate after spraying in a coastal forest ecosystem indicate that glyphosate is strongly adsorbed to the upper layers of soil and has a low propensity for leaching(2). Glyphosate residues dissipated with a half-life of 45-60 days. After 360 days, residues levels were 6-18% of initial levels(2). Field studies on eleven different soils covering a full range of soil types and geographical areas indicates an avg half-life of 60 days for glyphosate in soil(4). Other sources also report an avg half-life of 60 days from literature surveys(1,5).
TERRESTRIAL FATE: The half-life of glyphosate applied to forest foliage was 14.4 days(1) and that applied to two Finnish agricultural fields were 69 and 127 days, respectively(2). Persistence studies with glyphosate in sandy test sites in a boreal forest in Ontario, Canada indicate that the half-life of glyphosate was 24 days and residues were reduced to 
TERRESTRIAL FATE: In a Finnish study where the glyphosate was applied to two agricultural fields in September to control quackgrass and the fields plowed after six days, 76% and 10% remained in the field containing loam soil after 28 days and 8 months, respectively(1). The corresponding values for the field with fine silt was 92% and 53%. The loam soil in which degradation was more rapid had a higher respiration rate. In a similar study in eight forest soils in Sweden at higher temperatures, an avg 20% of the glyphosate applied in August was present in samples taken the following May(1). [(1) Muller MM et al; Bull Environ Contam Toxicol 27: 724-30 (1981)] PubMed Abstract
AQUATIC FATE: Based on a classification scheme(1), Koc values of 2,600 to 4,900(2), indicates that glyphosate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process because glyphosate exists as a zwitterion in water (3), and ionic species do not volatilize. The aerobic and anaerobic biodegradation half-life of glyphosate in a flooded silty clay loam sediment was 7 and 8.1 days, respectively(4). Glyphosate was stable to hydrolysis at pH 5, 7, and 9 at 5 to 35 deg C(5). According to a classification scheme(6), BCF values of 0.2 to 0.63 measured in fish(7,8), suggest bioconcentration in aquatic organisms is low(SRC).
AQUATIC FATE: When glyphosate enters water as runoff or inadvertent overspray or spray drift, it adsorbs strongly to sediment and particulate matter in the water column. It may also form insoluble complexes with metal ions and precipitate. Evidence from microcosm studies suggests that sediment adsorption and/or biodegradation represents the major dissipation process in aquatic systems(2). Glyphosate levels in sediment rise at first and then fall to very low or undetectable levels(2). After glyphosate was sprayed over two streams in the rainy coastal watershed of British Columbia, glyphosate levels in the streams rose dramatically after the first rain event, 27 hr postapplication, and fell to undetectable levels 96 hr postapplication(1). The highest residues were associated with sediments, indicating that they were the major sink for glyphosate. Residues persisted throughout the 171 day monitoring period. Suspended sediment is not a major mechanism for glyphosate transport in rivers(1). The half-lives of glyphosate in three forest ponds in Manitoba, Canada that were aerially spray in August was 1.51 to 1.99 days and glyphosate was not detected in any sample by day 38(2). The pond in which glyphosate had the longest half-life had much higher levels of calcium and magnesium than the other ponds.
AQUATIC FATE: In aerially treated forest brush fields in the Oregon Coast range, the concentration in streamwater peaked at 0.28 ppm shortly after spraying and declined sharply to undetectable levels in about 6 days(1). Concentrations in sediment increased slowly to a peak value of 0.55 ppm after 14 days and then slowly declined; at the end of the 55 day study the level was about 0.1 ppm. The concn pattern for aminomethylphosphonic acid, a glyphosphate metabolite in sediment was similar to that of glyphosate, but at much lower levels. Sediments adsorb glyphosate from flowing water; once adsorbed, it is not readily eluted. In experiments where glyphosate was added to water in two irrigation canals, the fractional reduction in load was 13 and 27% per km with uptake by the benthic sediment being 365 and 603 g/km(2). In two other experiments in which glyphosate was added to flowing water to simulate contamination during foliar spaying, 63% of the glyphosate was scavenged by sediment in 14 km and 43% was removed in 14 km(2). In a field study, glyphosate was sprayed on sediment in an irrigation channel in spring and 4 days afterwards the channel was filled with water. Based on the observed concentration levels, less than 7% of the applied glyphosate eluted with water(2).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glyphosate, which has a vapor pressure of 9.8X10-8 mm Hg at 25 deg C(2), is expected to exist solely in the particulate-phase in the ambient atmosphere. Particulate-phase glyphosate may be removed from the air by wet and dry deposition(SRC).

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