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Fosamine

Fosamine structure

Fosamine 

structure
  • CAS No:

    59682-52-9

  • Formula:

    C3H8NO4P

  • Chemical Name:

    Fosamine

  • Synonyms:

    Phosphonic acid,P-(aminocarbonyl)-,monoethyl ester;Phosphonic acid,(aminocarbonyl)-,monoethyl ester;Ethyl carbamoylphosphonic acid;Fosamine

Description

Fosamine is a phosphonic ester.

Fosamine Basic Attributes

153.07400

153.07

611-862-8

RS22J9RP83

DTXSID5043976

COLORLESS CRYSTALLINE SOLID|WHITE CRYSTALLINE SOLID

Characteristics

99.43000

0.98730

1.432g/cm3

175ºC

290.3ºC at 760 mmHg

129.4ºC

1.467

@ 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

0.53 mPa @ 25 °C

Henry's Law constant: 5X10-13 atm-cu m/mole (est).

Vap: 4x10-6 mm Hg at 25 °C

Corrosive to copper and brass.

Safety Information

AQUEOUS FORMULATIONS AND DILUTED SPRAYS ARE STABLE, BUT IT DECOMP IN ACID MEDIA IN DILUTE SOLN (5 MG/L) ... .|Stable in neutral and alkaline media.

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.

Toxicity

LD50 Rat oral 10125 mg active ingredient (as emulsifiable concentrate)/kg|LD50 Rat oral more than 2075 mg (containing surfactant)/kg|LD50 Guinea pig oral 7380 mg/kg|LD50 Rabbit percutaneous more than 1660 mg/kg|LC50 Rat oral 24000 mg/kg

Fosamine-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).

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.

The rate constant for the vapor phase reaction of fosamine-ammonium with photochemically produced hydroxyl radicals has been estimated to be 4.9X10-11 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 7.9 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). In aqueous hydrolysis studies using buffered water at 20 °C, less than 3% of initial fosamine-ammonium degraded over a 4 week period at pHs of 7 and 9(2); however, at pH 5, a degradation half-life of about 10 days was observed(2). Fosamine-ammonium was found to be stable (less than 2% degradation over 4 weeks) to direct photolysis and photosensitized photolysis (using riboflavin and anthraquinone sensitizers) in photolysis studies using sunlight and water at pH 7.9 and a Brandywine River water at pH 6.5(2); when sediments were added to the river water, degradation reached 45% after 4 weeks, but the degradation process was considered to be biological(2).

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).

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).

Based upon a vapor pressure of 4X10-6 mm Hg(1) and a water solubility of 1.79 kg/l at 25 °C(1), the Henry's Law constant for fosamine-ammonium can be estimated to be 5X10-13 atm-cu m/mole (SRC). This value of Henry's Law constant indicates that fosamine-ammonium is essentially nonvolatile from water(2).

Occupational exposure to fosamine-ammonium occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as a herbicide(1).

Drug Information

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.

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

1. SKIN CONTAMINATION SHOULD BE REMOVED PROMPTLY BY WASHING WITH SOAP AND WATER. CONTAMINATION OF THE EYES SHOULD BE TREATED IMMEDIATELY BY PROLONGED FLUSHING OF THE EYES WITH COPIOUS AMOUNTS OF CLEAN WATER. IF DERMAL OR OCULAR IRRITATION PERSISTS, MEDICAL ATTENTION SHOULD BE OBTAINED WITHOUT DELAY. /OTHER HERBICIDES/|2. INGESTIONS OF THESE HERBICIDES ARE LIKELY TO BE FOLLOWED BY VOMITING AND DIARRHEA DUE TO THE IRRITANT PROPERTIES OF MOST OF THE TOXICANTS. ... A. IF LARGE AMOUNTS OF HERBICIDE HAVE BEEN INGESTED, AND IF THE PATIENT IS FULLY ALERT, INDUCE EMESIS WITH SYRUP OF IPECAC, FOLLOWED BY SEVERAL GLASSES OF WATER. DOSAGE FOR ADULTS AND CHILDREN OVER 12 YEARS: 30 ML; DOSAGE FOR CHILDREN UNDER 12 YEARS 15 ML. WHEN VOMITING HAS STOPPED, GIVE ACTIVATED CHARCOAL. ADD SORBITOL TO THE CHARCOAL SLURRY UNLESS DIARRHEA HAS ALREADY COMMENCED. IF, FOR SOME REASON, THE PATIENT IS NOT FULLY ALERT, PUT IN PLACE A CUFFED ENDOTRACHEAL TUBE TO PROTECT THE AIRWAY, THEN ASPIRATE AND LAVAGE THE STOMACH WITH A SLURRY OF ACTIVATED CHARCOAL. LEAVE A QUANTITY OF CHARCOAL, WITH SORBITOL, IN THE STOMACH BEFORE WITHDRAWING THE STOMACH TUBE. REPEATED ADMINISTRATION OF CHARCOAL AT HALF OR MORE THE INITIAL DOSAGE EVERY 2-4 HOURS MAY BE BENEFICIAL. /OTHER HERBICIDES/|2. B. IF THE AMOUNT OF INGESTED HERBICIDES WAS SMALL, IF EFFECTIVE EMESIS HAS ALREADY OCCURRED, OR IF TREATMENT IS DELAYED, ADMINISTER THE ACTIVATED CHARCOAL AND SORBITOL BY MOUTH. C. IF SERIOUS DEHYDRATION AND ELECTROLYTE DEPLETION HAVE OCCURRED AS A RESULT OF VOMITING AND DIARRHEA, MONITOR BLOOD ELECTROLYTES AND AND FLUID BALANCE AND ADMINISTER INTRAVENOUS INFUSIONS OF GLUCOSE, NORMAL SALINE RINGER'S SOLUTION, OR RINGER'S LACTATE TO RESTORE EXTRACELLULAR FLUID VOLUME AND ELECTROLYTES. FOLLOW THIS WITH ORAL NUTRIENTS AS SOON AS FLUIDS CAN BE RETAINED. FLUIDS SERVE TO SUPPORT EXCRETION OF THE TOXICANTS. D. SUPPORTIVE MEASURES ARE ORDINARILY SUFFICIENT FOR SUCCESSFUL MANAGEMENT OF EXCESSIVE EXPOSURES TO THESE HERBICIDES. /OTHER HERBICIDES/

ammonium ethyl carbamoylphosphonate

Fosamine Use and Manufacturing

Methods of Manufacturing

/PRODUCED/ BY REACTION OF TRIETHYL PHOSPHITE WITH METHYL CHLOROFORMATE & AMMONIA.

KRENITE BRUSH CONTROL AGENT IS A LIQUID FORMULATION FOR FIELD BINDWEED AND LEAFYSPURGE CONTROL IN NONCROPLAND AREAS. GROWTH REGULANT.

... 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'.|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.

RESIDUES IN PLANT TISSUES & IN SOIL MAY BE DETERMINED BY GLC OF A DERIVATIVE.|Determination of fosamine-ammonium by iodometric titration. Residue analysis is by GLC with phosphorus specific detection.

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:153.07
XLogP3:-1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:153.01909473
Monoisotopic Mass:153.01909473
Topological Polar Surface Area:89.6
Heavy Atom Count:9
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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