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Home > Encyclopedia > Propham

Propham

Propham structure

Propham 

structure
  • CAS No:

    122-42-9

  • Formula:

    C10H13NO2

  • Chemical Name:

    Propham

  • Synonyms:

    Carbamic acid,N-phenyl-,1-methylethyl ester;Carbanilic acid,isopropyl ester;Carbamic acid,phenyl-,1-methylethyl ester;Y 2;Chem-Hoe;IFK;INPC;IPC;Isopropyl carbanilate;Isopropyl phenylcarbamate;O-Isopropyl N-phenylcarbamate;Propham;Tuberit;Profam;Agermin;IPPC;Birgin;Collavin;Tixit;Isopropyl phenylurethane;Tuberite;N-Phenyl-O-isopropylurethane;NSC 2105

  • Categories:

    Agrochemicals  >  Herbicides

Description

White to gray crystalline needles; odorless when pure. Mp 84C (technical grade). Soluble in alcohol, acetone, isopropyl alcohol; insoluble in water. Propham is a colorless crystalline solid.Colorless crystalline solid.


Propham is a colorless crystalline solid.


Propham is a colorless crystalline solid.|Propham is a carbamate ester that is the isopropyl ester of phenylcarbamic acid. It is a selective herbicide used for the control of annual grasses and some broad-leaf weeds and is also a growth regulator for control of sprouting in stored potatoes. It has a role as a herbicide and a plant growth retardant. It is a carbamate ester and a member of benzenes.

Propham Basic Attributes

179.22

179.22

204-542-0

Y647G714RY

2105

3077|2902

DTXSID7020766

White crystalline solid|Colorless crystals|WHITE NEEDLES FROM ALCOHOL

29242990

Characteristics

38.33000

2.65

Dark brown, blue-black Solid

1.09 g/cm3 @ Temp: 20 °C

90 °C

311.75°C (rough estimate)

11 °C

1.4989 (estimate)

9.99e-04 M

APPROX 4°C

1.40e-04 mmHg

Oral-Rat LD50: 1000 mg/kg; Oral-Mouse LD50: 2160 mg/kg

Combustion produces toxic nitrogen oxide gas

Odorless when pure

Henry's Law constant = 1.8X10-7 atm cu m/mol at 25 °C (est)

150.76 Ų [M+Na]+

Sublimes upon heating; decomposition at 150 °C.|Considerable vapor pressure at 85 °C. Sublimes slowly at room temperature.|Hydroxyl radical reaction rate constant = 5.2X10-11 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Carbamates

PROPHAM is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

NON-CORROSIVE

Safety Information

I; II; III

6.1

UN12303/PG2

3

36/37/38-39/23/24/25-23/24/25-11-22

26-36-45-16-7-36/37

FD9100000

F,T,Xn

Warehouse ventilated, low temperature and dry

Unlimited ... sublimes from granular formulation at high temp; low temp may cause crystallization in EC formulation

P210-P260-P280-P301 + P310-P311

H225-H301 + H311 + H331-H370

[40 CFR 240-280, 300-306, 702-799 (7/1/2005)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U373, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|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.

Hydrolysed slowly in acidic and alkaline media.

WHO; Environ Health Criteria V12: Isopropyl Phenylcarbamate (1976)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 48 companies from 3 notifications to the ECHA C&L Inventory.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

Not considered flammable

A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. The system incorporates a two-stage treatment process. The first step is the flocculation/coagulation and sedimentation of the pesticide contaminated wash water. The supernatant from the first step is then passed through activated C columns.|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.

Avoid breathing of vapor or spray mist. Use with adequate ventilation.|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.|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.|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.

The parent compd may cause local skin irritation, but are not skin sensitizers. /Chloropham and related carbamate herbicides/

U373; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). The Agency may adjust the statutory RQ for this hazardous substance in a future rulemaking; until then the statutory one-pound RQ applies.

U373; As stipulated in 40 CFR 261.33, when isopropyl phenylcarbamate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Isopropyl phenylcarbamate was not detected in 35 wells from 3 counties in CA between July 1, 1994 and June 30, 1995(1).

Compounds in.../the phenylcarbamate and carbanilate herbicide/ group incl propham. ...they are very immobile in soil systems. ...these cmpd have been shown to be inactivated by adsorption to soil org matter. ... The mechanism of adsorption to soil org matter is thought to involve hydrogen bonding between the carboxyl groups of the org matter and the nitrogen and carbonyl oxygen of the carbamate.|BIOASSAY TESTS INDICATE HALF LIFE...TO BE ABOUT 15 DAYS @ 16 °C & 5 DAYS @ 29 °C. HOWEVER, THE RATE OF DISSIPATION CAN VARY GREATLY WITH THE MICROBIAL ACTIVITY AND MOISTURE LEVEL OF A GIVEN SOIL.

Toxicity

moderately toxic

LD50 Rat (male) oral 3724 mg/kg|LD50 Rat (female) oral 4315 mg/kg|LD50 Mouse oral 3000 mg/kg|LD50 Mouse ip 1000 mg/kg|For more Non-Human Toxicity Values (Complete) data for ISOPROPYL PHENYLCARBAMATE (6 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ /In male Mallards 3 months old/ regurgitation, high carriage, goose-stepping ataxia, falling when walking, walking with aid of wings. Signs persisted 2 to 4 wk after single oral administration.|/AQUATIC SPECIES/ Both propham and chloropropham were embryotoxic and teratogenic in amphibians.|/AQUATIC SPECIES/ The endomembrane network of the chlamydomonad alga, Gloeomonas kupferri, can be disrupted by the herbicide, isopropyl N-phenyl carbamate (IPC).

Isopropyl phenylcarbmate's production may result in its release to the environment through various waste streams; it's former use in the US as a herbicide(1) will have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values ranging from 51 to 65(2,3) indicate that isopropyl phenylcarbmate is expected to have very high mobility in soil(SRC). Volatilization of isopropyl phenylcarbmate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), derived from a vapor pressure of 1X10-4 mm Hg(4) and a water solubility of 1.79 mg/L(5). Isopropyl phenylcarbmate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Pure culture studies show that phenylcarbates are biodegraded to catechol which is then further metabolized in the TCA cycle(6). Isopropyl phenylcarbamate biodegrades more rapidly in soil that was previously treated with isopropyl phenylcarbamate(7). After 60, days 70% of isopropyl phenylcarbamate from soil previously treated with the pesticide was degraded into CO2 compared to the 20% degraded by soil that had never been treated with the pesticide(7). Similar results were obtained with soil that had been treated with the pesticide carbetamide(8). Isopropyl phenylcarbamate is stable in the presence of anaerobic microorganisms(9).|TERRESTRIAL FATE: Isopropyl phenyl carbamate was applied as a spray on sandy loam soil taken from Bagbroke Hill Farm(1). The soil was then repotted and Italian rye grass was grown under greenhouse environment. Analysis of dry weight samples showed that isopropyl phenylcarbamate had a half life of less than 4.5 weeks in soil where Italian rye grass was grown(1).|AQUATIC FATE: Based on a classification scheme(1), measured Koc values ranging from 51 to 65(2,3) indicate that isopropyl phenylcarbmate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), derived from a vapor pressure of 1X10-4 mm Hg(5) and a water solubility of 1.79 mg/L(6). Isopropyl phenylcarbmate has been shown to be resistant to hydrolysis in the environment(7). According to a classification scheme(8), an estimated BCF of 20(SRC), from its log Kow of 2.6 (9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Pure culture studies show that phenylcarbamates are biodegraded to catechol which is then further metabolized in the TCA cycle(11). Studies show that biodegradation in water may be an important fate process(12,13); however this reaction may be dependent on concentration of the sample(12). Isopropyl phenylcarbamate is stable in the presence of anaerobic microorganisms(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl phenylcarbmate, which has a vapor pressure of 1.4X10-4 mm Hg at 25 deg(2), is expected to exist solely as a vapor phase in the ambient atmosphere. Vapor-phase isopropyl phenylcarbmate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.3 hours(SRC), calculated from its rate constant of 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Isopropyl phenylcarbmate does not contain chromophores that absorb at wavelengths >290 nm and has been shown not to be susceptible to direct photolysis by sunlight(4).

The carbamate herbicide propham photodecomposes by at least two pathways.|The rate constant for the vapor-phase reaction of isopropyl phenylcarbmate with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Isopropyl phenylcarbmate has been shown to be resistant to hydrolysis in the environment(2). Isopropyl phenylcarbmate does not contain chromophores that absorb at wavelengths >290 nm and has been shown not to be susceptible to direct photolysis by sunlight(3).

An estimated BCF of 20 was calculated for isopropyl phenylcarbmate(SRC), using a log Kow of 2.6(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

67.61 L/kg|...PROPHAM IS READILY ADSORBED TO ACTIVATED CARBON & ORG MATTER...BOND IS RATHER WEAK, ALLOWING WATER TO LEACH PROPHAM THROUGH SOIL COLUMN.|The Koc of isopropyl phenylcarbmate has reported values between 51 to 65(1,2). According to a classification scheme(3), this estimated Koc value suggests that isopropyl phenylcarbmate is expected to have very high mobility in soil.

INCR FIELD MOISTURE CAPACITY & TEMP GREATLY INCR VAPOR LOSSES TO POINT WHERE @ 35 °C VOLATILITY MAY BE MAJOR MEANS OF DISSIPATION.|The Henry's Law constant for isopropyl phenylcarbmate is estimated as 1.8X10-7 atm-cu m/mole(SRC) derived from a vapor pressure of 1X10-4 mm Hg(1) and a water solubility of 1.79 mg/L(2). This Henry's Law constant indicates that isopropyl phenylcarbmate is expected to be essentially nonvolatile from water and moist soil surfaces(2). Isopropyl phenylcarbmate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Isopropyl phenylcarbamate was detected but not quantified in 1 out of 1,060 wells sampled in the US from 1971-1991(1). In a separate study, isopropyl phenylcarbamate was detected with 0.5% frequency in the public stream water of Denver CO with a maximum concentration of 0.07 ug/L(2).|RAIN/SNOW/FOG: Isopropyl phenylcarbamate was not detected in rainwater collected from Konigsmoor, Germany during 1996(1).

Isopropyl phenylcarbamate was detected in boiled potatoes(1). There were 97 reports of isopropyl carbamate in imported food in Sweden from 1990-1994(2).

Main route of excretion of propham by goat was via urine. Small amount appeared in milk and feces.

Occupational exposure and general population exposure should be low or non-existent since isophenyl carbamate is no longer produced or used in the US (1998). In the past, isopropyl phenyl carbamate was applied directly to the potato, clover, lentil, sugar beet, safflower, pea, flax and spinach crops as an herbicide and exposure to this compound was primarily by dermal contact and in the field where it was applied. (SRC)

Drug Information

Main route of excretion of propham by goat was via urine. Small amount appeared in milk and feces.|After oral or ip administration of propham to rats, 80% of (14)C-isopropyl label appeared in urine within 4 days. Smaller amount appeared in feces and respired air.|...Herbicide-related material was distributed throughout the body /of treated rats/, with highest concentration in the kidneys. ...Approximately 30% of iv dose of propham was excreted in 6 hr bile.|Propham is absorbed through coleoptiles of emerging grass seedlings and to lesser degree through roots of plants. ...Absorbed slowly through leaves... propham or its metabolites are readily transported acropetally following root absorption.|The tissue distribution and excretion of 14C-labelled propham (purity >99%, specific activity of chain-labelled molecule 4.9 mCi/mmol and of ring-labelled molecule 4.1 mCi/mmol) were investigated in adult female Wistar rats (mean body-weight 270 g). A single oral dose (2 animals per dose) of 0, 0.67, 19, 38, or 75 mg/kg bw 14C-labelled propham (5 uCi in 1.0 mL of 20% aqueous ethanol solution) was administered by intubation. Rats were housed individually in glass metabolism cages; expired air was continuously monitored for radioactivity for 72 hr. The feces and urine samples were collected at 24, 48, and 72 hr and analyzed for 14C by liquid scintillation counting. The urine was analyzed by paper chromatography and thin-layer chromatography. In a similar experiment, single rats were killed at various times (1-24 hr) after administration of a single dose of 0.81 mg/kg bw 14C-labelled propham/kg bw (5 uCi in 1.0 mL of a 20% aqueous ethanol solution). Tissue samples (kidneys, liver, blood, lungs, heart, spleen, intestine, brain, muscle, and fat) were freeze-dried, and analyzed for 14C... . The average 3-day excretion of radioactivity in urine, feces, and CO2 was 80, 5, and 5%, respectively after chain-labelling of propham, and 85, 5, and 0%, respectively after ring-labelling of propham. There was no significant difference in the rate of excretion or the route of elimination among rats receiving different dosages. The radioactivity was distributed in all examined tissues with the highest concentrations in the kidneys.

Isopropyl N-phenylcarbamate yields aniline in arthrobacter and in achromobacter... . /from table/|Soybean plants were root-treated with propham-(14)C. Analyses of metabolites indicated...glycosides of 2-hydroxypropham and...one...was probably beta-o-glucoside...|After dosing goat and chicken with labeled propham, analyses...showed presence of para-sulfate derivatives in goat milk and goat carcasses. Glucuronide was also found in chicken carcass... .|After administration of phenyl-(14)C-labeled propham to goat /and rats/... metabolites identified were: 1. glucuronic acid conjugate of 4-hydroxypropham, 2. sulfate ester of 4-hydroxypropham, 3. glucuronic acid conjugate of 4-hydroxyacetanilide, 4. sulfate ester of 2-hydroxyaniline, 5. conjugate of 2-hydroxyisopropyl 4-hydroxycarbanilate, 6. sulfate ester of 2-hydroxypropham, 7. sulfate ester of 4-hydroxyacetanilide /rats only/... Partial identification of other metabolites from goat indicated presence of: 1. 4-hydroxypropham conjugate, 2. 2-hydroxypropham conjugate, 3. para-aminophenol conjugate, 4. 3,4-dihydroxypropham conjugate.|For more Metabolism/Metabolites (Complete) data for ISOPROPYL PHENYLCARBAMATE (8 total), please visit the HSDB record page.

In rats, average biological half-life for IPC in internal organs was 5.0 hr, in brain, muscle and fat tissue, 13.3 hr.|The average biological half-life /in adult female Wistar rats/ of propham in most organs was short, ranging between 3 and 8 hr. However, in brain, fat, and muscle, the half-life was about twice the value for other organs.

Root and epicotyl growth inhibition are...phytotoxic effect...in intact plants. Among its actions at cellular level...disrupts normal cell division, inhibits protein and amylase synthesis, inhibits photolytic activity of isolated chloroplasts and effects activity of messenger RNA.|The effects of propham ... on O uptake, ATP synthesis, cell division and cell cycle distribution in root tips of pea (Pisum sativum) (Alaska) are reported. At the lowest concn tested ( ... propham, 1.2 .times. 10-6M) a reduction in the number of cells able to enter into mitosis was observed. ... At the higher range of concn tested ... propham (1.2 .times. 10-3M) caused a rapid decrease in number of mitosis so that by 6 hr <1% of the total cells were dividing and all of them were abnormal, by 24 hr this level was reduced to .apprx. 0.2%.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension if signs of hypovolemia are present, administer fluid cautiously. Watch for signs of pulmonary edema ... . Administer atropine. Correct hypoxia before administration ... . In severely poisoned patients, administer pralidoxime chloride (2 PAM). DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. Rarely is diazepam necessary ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Carbamates and related compounds/|Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Carbamates and related compounds/

isopropyl N-phenylcarbamate

Propham Use and Manufacturing

Methods of Manufacturing

Allen, US patent 2,615,916 (1952 to Columbia-Southern Chem Corp)... /SRP: A method of separating isopropyl n-phenyl carbamate from its reaction mixture created by reaction of an isopropyl haloformate with aniline in the presence of water and a base at a temperature at which solid isopropyl n-phenyl carbamate is produced, which comprises heating the reaction mixture to a temperature above the melting point of the carbamate but below the temperature at which the water phase in the mixture biols, thereby forming two immiscible liquid layers, separating the layer containing the product, steam distilling impurities from the product atomizing the product and chilling it to form a uniform, granular, powder-like product./|Reaction of phenyl isocyanate with isopropyl alcohol; or reaction of aniline with isopropyl chloroformate

Uses

Herbicide, applied as a spray to the soil.

Production

(1972) 1.82X10+8 GRAMS (EST)|(1975) 9.08X10+7 GRAMS (CONSUMPTION)

100% IN AGRICULTURAL APPLICATIONS AS A SELECTIVE HERBICIDE FOR ANNUAL GRASSES & BROADLEAF WEEDS ON FORAGE CROPS (CLOVER & ALFALFA), FLAX, LETTUCE, SAFFLOWER, SPINACH, SUGAR BEETS, LENTILS, & PEAS (1975)

EMULSIFIABLE CONCENTRATE (2 LB/GAL), GRANULES (10% & 15%), FLOWABLE SUSPENSION (4 LB/GAL). WETTABLE POWDER 50% (TRI-HERBICIDE-1PC*). COMBINATIONS: TANK MIX WITH BENEFIN FOR WEED CONTROL IN LETTUCE. PROPHAM WITH CHLORPROPHAM + FENURON (BEET-KLEEN*). PROPHAM WITH LENACIL (BAN-HOE*).|Technical grade is 99% pure.|For EC formulation water is used at 10 to 40 gal/acre. Granular formulation involves binding 15% propham onto sand-core base.|AGERMIN|For more Formulations/Preparations (Complete) data for ISOPROPYL PHENYLCARBAMATE (23 total), please visit the HSDB record page.

Carbamic acid, N-phenyl-, 1-methylethyl ester: INACTIVE|SELECTED BY TEMPLEMAN, WG & SEXTON, WA, NATURE, 156, 630, 1945; PROC ROY SOC 133B, 480, 1946, AS MOST ACTIVE OF SERIES OF ARYLURETHANES AS GROWTH SUBSTANCES; BRITISH PATENT 574,995.|Granular formulations of IPC on soils at 4 lb/acre rate lost more than spray applications at same rate & some protection against vapor loss was achieved by covering herbicide with 1/8- to 1/4-in layer of soil.

Propham was extracted from biological material (liver) with acetonitrile (MeCN). The extract was washed with hexane, and pesticides partitioned into CH1Cl2, methylated, and determined by capillary gas chromatog-mass spectrometry using SE-52, and He carrier gas.|Determination of fluorescent pesticides and metabolites by reversed-phase high-performance liquid chromatography.|Method: USGS-NWQL O-2060-01; Procedure: Graphitized carbon-based solid-phase extraction and HPLC-MS; Analyte: isopropyl phenylcarbamate; Matrix: filtered surface water and ground water; Detection Limit: 0.0048 ug/L.|Method: AOAC 992.14; Procedure: liquid chromatographic method with ultraviolet detector; Analyte: isopropyl phenylcarbamate; Matrix: finished drinking water; Detection Limit: not provided.|Product analysis by hydrolysis, the liberated carbon dioxide being determined titrimetrically; ... mixture with chlorpropham by glc. Residues determined by hydrolysis to aniline, a derivative of which is estimated by glc.

Agrochemicals -> Herbicides, Plant Growth Regulators|Pharmaceuticals|HERBICIDES

Food Contaminant -> CONTAMINANT;

Computed Properties

Molecular Weight:179.22
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:38.3
Heavy Atom Count:13
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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