HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.9
  1. Home
  2. /Compound

Fosamine

HCID 33257
New noteNew reactionRequest quotesPrint preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
25954-13-6
Standard SMILES
CCOP(=O)(O)C(N)=O
InChIKey
UCHDFLNGIZUADY-UHFFFAOYSA-N
Molecular formula
C3H8NO4P
Average molar mass
153.07 g/mol
Monoisotopic mass
153.01909473

Overview

Fosamine is a phosphonic ester.

Names & identifiers

Preferred name
Fosamine
IUPAC
carbamoyl(ethoxy)phosphinic acid
English name
fosamine
Molecular formula
C3H8NO4P
Molecular weight
153.07

Names & synonyms

FOSAMINEcarbamoyl(ethoxy)phosphinic acid59682-52-9Ethyl hydrogen carbamoylphosphonateEthyl carbamoylphosphonic acidMonoethyl (aminocarbonyl)phosphonateRS22J9RP83Phosphonic acid, (aminocarbonyl)-, monoethyl esterDTXSID5043976Ammonium-aethyl-carbamoyl-phosphonatRefChem:141364DTXCID3023976
Show more names
ETHYLCARBAMOYLPHOSPHONATECarbamoylphosphonic acid hydrogen ethylCarbamoylphosphonic acid hydrogen ethyl esterPhosphonic acid, P-(aminocarbonyl)-, monoethyl ester
611-862-8Fosamine [BSI:ISO]BRN 2206645UNII-RS22J9RP83Fosamine [ISO]SCHEMBL64451CHEMBL3306792CHEBI:81962

Database identifiers

CAS
25954-13-6、59682-52-9
PubChem CID
33257
DTXSID
DTXSID5043976
ChEMBL
CHEMBL3306792
ChEBI
CHEBI:81962
UNII
RS22J9RP83
EC Number
611-862-8
Nikkaji
J1.092H

Properties

Computed structural properties

XLogP
-1.5
Topological polar surface area
89.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
9
Formal charge
0
Complexity
156

Experimental & physicochemical properties

Pesticides · 2 items

Herbicides

Active substance -> EU Pesticides database: Not approved

Density1.33
Color/Form · 2 items

COLORLESS CRYSTALLINE SOLID

WHITE CRYSTALLINE SOLID

Solubility · 3 items

@ 25 °C: 1.79 KG/KG WATER, 300 MG/KG ACETONE, 400 MG/KG BENZENE, 12 G/KG ETHANOL, 1.4 G/KG DIMETHYLFORMAMIDE, 158 G/KG METHANOL, 200 MG/KG HEXANE

SLIGHTLY SOL IN MOST COMMON ORGANIC SOLVENTS

0.04 g/kg chloroform at 25 °C

CorrosivityCorrosive to copper and brass.
DecompositionDecomposes in dilute solutions of acids.
Melting Point175 °C
Vapor Pressure0.53 mPa @ 25 °C
Stability/Shelf Life · 2 items

AQUEOUS FORMULATIONS AND DILUTED SPRAYS ARE STABLE, BUT IT DECOMP IN ACID MEDIA IN DILUTE SOLN (5 MG/L) ... .

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ammonium ethyl carbamolyphosphonate is found on List B. Case No: 2355; Pesticide type: Herbicide; Case Status: RED Approved 12/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Ammonium ethyl carbamolyphosphonate; Data Call-in (DCI) Date(s): 06/11/91, 03/14/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Safety & protection

Preventive Measures · 3 items

Avoid contact with skin, syes, and clothing. Do not contaminate water by cleaning of equipment or disposal of wastes.

Irritating to eyes. May irritate nose, throat, skin. Avoid breathing spray or mist.

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.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

THE ELIMINATED (14)C IN URINE & FECES WAS 87% INTACT FOSAMINE AND ABOUT 13% CARBAMOYLPHOSPHONIC ACID.

Metabolism of organophosphates occurs principally by oxidation, and hydrolysis by esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Fosamine rapidly passes through the body; elimination is primarily in the feces and less in the urine. It does not bioaccumulate (build up) in mammals.

Absorption, Distribution and Excretion · 2 items

WHEN ADMIN AS A SINGLE ORAL DOSE TO PRECONDITIONED RATS BY INTRAGASTRIC INTUBATION, RADIOACTIVITY WAS RAPIDLY ELIMINATED IN FECES (87%) & URINE (13%). TRACE AMT FOUND IN THE GI TRACT, HIDE & EXHALED AIR RADIOACTIVITY FOUND IN BODY TISSUES AFTER 72 HR.

Uptake via leaves, (not via roots). No downward transport in the plant.

Uses & manufacturing

Uses · 3 items

BRUSH CONTROL AGENT & GROWTH REGULANT

CONTACT HERBICIDE

Used as a herbicide to control growth of woody plants.

Methods of Manufacturing/PRODUCED/ BY REACTION OF TRIETHYL PHOSPHITE WITH METHYL CHLOROFORMATE & AMMONIA.
Formulations/PreparationsKRENITE BRUSH CONTROL AGENT IS A LIQUID FORMULATION FOR FIELD BINDWEED AND LEAFYSPURGE CONTROL IN NONCROPLAND AREAS. GROWTH REGULANT.
General Manufacturing Information · 4 items

... FOSAMINE-AMMONIUM ... WAS INTRODUCED /IN 1974/ BY EI DU PONT DE NEMOURS & CO(INC) (US PATENT 3627507; 3846512) AS CODE NUMBER 'DXP 1108', TRADE MARK 'KRENITE'.

Suppliers

Loading…

Open inquiries

Loading…

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Stable in neutral and alkaline media.

Other Experimental PropertiesVap: 4x10-6 mm Hg at 25 °C

Physicochemical properties

Boiling point
290.3 · 290.3±23.0 °C(Predicted)
Density
1.432 · 1.432±0.06 g/cm3(Predicted)
pka
0.86 · 0.86±0.50(Predicted)
EWG's Food Scores
1 · 1
FDA UNII
22 J9RP83 · RS22J9RP83
EPA Substance Registry System
Phosphonic acid, (aminocarbonyl)-, monoethyl ester (59682-52-9)

Toxicology

Treatment · 1 item

For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 item

Occupational exposure to fosamine occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as a herbicide. Fosamine has low to very low toxicity if individuals accidentally inhale or eat residues and has moderate toxicity if touched. It is not irritating to the eyes, but it can cause mild to moderate skin irritation. Fosamine can cause moderate eye injury or irritation. In one subchronic oral study, the laboratory animals given the highest dose exhibited some statistically significant effects, including effects to the kidneys, bladder and decreases in body weight.

Ecotoxicity Values · 5 items

LD50 Mallard duck oral more than 4150 mg (as emulsifiable concentrate)/kg

LD50 Bobwhite quail oral more than 4150 mg (as emulsifiable concentrate)/kg

LC50 Bluegill 278 mg active ingredient (as emulsifiable concentrate)/l/96 hr /Conditions of bioassay not specified/

LC50 Rainbow trout more than 415 mg active ingredient (as emulsifiable concentrate)/l/96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for FOSAMINE (6 total), please visit the HSDB record page.

Environmental Fate · 5 items

AQUATIC FATE: STUDIES SHOWED THAT IT IS STABLE FOR EXTENDED PERIODS IN NEUTRAL OR ALKALINE WATER.

TERRESTRIAL FATE: UNDER FIELD CONDITIONS T/2 IN SOIL WAS APPROX 1 WK FOLLOWING TREATMENT OF PRACTICAL USE LEVELS.

Terrestrial Fate: Rapidly decomposed by soil microorganisms. Half-life in soil is about 10 days.

TERRESTRIAL FATE: AT 10 PPM IT DID NOT AFFECT THE SOIL POPULATION COUNT OF FUNGI & BACTERIA OVER AN 8 WK PERIOD. IT HAD NO EFFECT ON THE SOIL NITRIFICATION PROCESS.

For more Environmental Fate (Complete) data for FOSAMINE (7 total), please visit the HSDB record page.

Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity SummaryFosamine is an eye irritant. It likely binds to or modifies the TRPA1 protein which leads to a lachrymatory (tearing) response.
Signs and Symptoms · 1 item

Fosamine has low to very low toxicity if individuals accidentally inhale or eat residues and has moderate toxicity if touched. It is not irritating to the eyes, but it can cause mild to moderate skin irritation. Fosamine is not a skin sensitizer.

Soil Adsorption/Mobility · 1 item

In field studies (conducted in DE, FL, and IL), greenhouse studies, and soil column studies, fosamine-ammonium was found to leach very little, either downward or laterally(1); most undegraded fosamine-ammonium remained in the upper 4 inches of soil(1).

Artificial Pollution SourcesFosamine-ammonium's use as a contact herbicide(1-3) releases the compound directly to the environment through applications in sprays and other routes of application(SRC).
Environmental Biodegradation · 1 item

Laboratory studies in biometer flasks on two soil types (pHs of 6.4 and 6.5) treated with C-14 fosamine-ammonium demonstrated rapid degradation by microbial action(1); 14-CO2 evolution in nonsterile soils reached 45-75% after 90 days(1); in soil sterilized by a single autoclaving at steam pressure for 15 min, 14-CO2 evolution was only 8-18%(2).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 item

Based upon a water solubility of 1.79 kg/L at 25 °C(1), the BCF of fosamine-ammonium can be estimated to be 0.2 from a recommended regression derived equation(2,SRC). The BCF value indicates that bioconcentration in aquatic organisms is not an important fate process(SRC). In bioaccumulation studies using channel catfish and (14)C fosamine-ammonium, fosamine-ammonium BCFs of less than 1 were measured(2).

Regulatory information

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ammonium ethyl carbamolyphosphonate is found on List B. Case No: 2355; Pesticide type: Herbicide; Case Status: RED Approved 12/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Ammonium ethyl carbamolyphosphonate; Data Call-in (DCI) Date(s): 06/11/91, 03/14/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

USED AS A FOLIAR SPRAY @ RATES OF 1 1/2 TO 3 GALLONS PRODUCT (6 TO 12 POUNDS AI)/ACRE APPLIED IN LATE SUMMER OR EARLY FALL FOR CONTROL &/OR GROWTH SUPPRESSION OF MANY WOODY SPECIES. SUSCEPTIBLE TREATED PLANTS NORMALLY FAIL TO REFOLIATE DURING GROWING SEASON FOLLOWING TREATMENT & SUBSEQUENTLY DIE. KRENITE MAY BE USED ON NONCROPLAND AREAS SUCH AS RAILROAD, PIPELINE, UTILITY & HIGHWAY RIGHTS-OF-WAY, DRAINAGE DITCHBANKS, STORAGE AREAS, INDUSTRIAL PLANT SITES & OTHER SIMILAR AREAS INCLUDING LAND ADJACENT TO & SURROUNDING DOMESTIC WATER SUPPLY RESERVOIRS, SUPPLY STATIONS, LAKES & PONDS. ... FOR SELECTIVE USE IN FORESTRY (CONTROL OF HARDWOODS IN CONIFERS) & FOR FIELD BINDWEED CONTROL IN NONCROPLAND AREAS.

Not to be used on food or feed crops.

Compatible with dalapon-sodium. In other cases, a preliminary test is recommended. ... Do not spray before rain in order to ensure drying of the spray deposits.

Applications · 1 item

DescriptionFosamine is an organophosphate herbicide and plant growth inhibitor. It is highly soluble in water, is not volatile and is not usually persistent in soil systems. It has a low mammalian oral toxicity but may be a neurotoxin. Available ecotoxicity data is limited but tends to be low.

Additional notes

DefinitionChEBI: Fosamine is a phosphonic ester.