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Chlorpropham

Chlorpropham structure

Chlorpropham 

structure
  • CAS No:

    101-21-3

  • Formula:

    C10H12ClNO2

  • Chemical Name:

    Chlorpropham

  • Synonyms:

    Carbamic acid,N-(3-chlorophenyl)-,1-methylethyl ester;Carbanilic acid,m-chloro-,isopropyl ester;Carbamic acid,(3-chlorophenyl)-,1-methylethyl ester;Y 3;Chloro-IPC;Chloropropham;Chlorpropham;CI-IPC;CIPC;Elbanil;Isopropyl 3-chlorocarbanilate;Isopropyl N-(3-chlorophenyl)carbamate;Metoxon;Preventol 56;Triherbicide CIPC;Chlor IFC;Isopropyl m-chlorocarbanilate;Nexoval;Preventol;Liro CIPC;Chlor IPC;m-Chlorocarbanilic acid isopropyl ester;Furloe 3EC;Isopropyl N-(m-chlorophenyl)carbamate;Chlor IFK;Cl-IFK;Furloe;Bygran;Mirvale;Bud Nip;Keim-Stop;IPCPC;NSC 29466;Shield Potato Sprout Inhibitor;Neo Stop 5;11097-02-2

  • Categories:

    Agrochemicals  >  Plant Growth Regulators

Description

beige to brown solidChEBI: A carbamate ester that is the isopropyl ester of 3-chlorophenylcarbamic acid.Brown chunky solid.A solid with low melting point of 41.4 ℃. The density is d30 1.180 and the refractive index is nD20 (after cooling) 1.5395.At 25 C, the solubility in the water is 89mg/L, and the degree of melting in the oil is medium (10% in the kerosene). It can be mixed with the lower alcohols, aromatics and most organic solvents. The purity of the industrial product is 98.5%, and the me


Isopropyl-n-(3-chlorophenyl)carbamate is a brown chunky solid. (NTP, 1992)|COLOURLESS-TO-BROWN CRYSTALS.


Isopropyl-n-(3-chlorophenyl)carbamate is a brown chunky solid. (NTP, 1992)|Chlorpropham is a carbamate ester that is the isopropyl ester of 3-chlorophenylcarbamic acid. It has a role as a herbicide and a plant growth retardant. It is a carbamate ester, a member of benzenes and a member of monochlorobenzenes.|A carbamate that is used as an herbicide and as a plant growth regulator.

Chlorpropham Basic Attributes

213.66

213.66

202-925-7

0HBU04R8B0

1500

29466

3077

DTXSID7020764

Colorless solid|Light-tan powder|Light brown crystalline solid

2924299035

Characteristics

38.3

3.4

light tan crystalline

1.180 g/cm3 @ Temp: 30 °C

40.7-41.1 °C

149 °C @ Press: 2 Torr

247°C

nD20 1.5388

H2O: 0.009 g/100 ml very poor

APPROX 4°C

24 mPa (1.8X10-4 mm Hg) at 20 deg C (98% pure)

Oral-Rat LD50: 1200 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Faint characteristic odor

Henry's Law constant: 5.7X10-7 atm cu m/mol at 25 °C /Estimated/

Technical grade 98.5% pure; melting point: 38.5-40 °C (tech); log Kow: 3.79 at pH 4, 20 °C; Henry's law constant: 0.047 Pa cu m/mol at 20 °C; stable to UV light; decomposes above 150 °C; hydrolyzed slowly in acidic or alkaline media|Commercial product is a liquid|Hydroxyl radical reaction rate constant = 4.0X10-11 cu cm/molec-sec at 25 °C /Estimated/

Insoluble in water.

Carbamates

ISOPROPYL-N-(3-CHLOROPHENYL)CARBAMATE 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

III

9

UN 3077 9/PG 3

2

22-51/53-36-20/21/22-11

61-36/37-26-16

FD8050000

Xn,N,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.

P273-P301 + P312 + P330-P391-P501

H302-H351-H373-H411

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.|Chlorpropham should be incinerated at high temp in a unit with effluent gas scrubbing to absorb hydrogen chloride. Recommendable method: Incineration.

Toxicology Review: Residue Reviews 63: 1 (1976)|USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Chlorpropham. EPA 738-R-96-023 October 1996. Available from the Database Query page at http://cfpub.epa.gov/oppref/rereg/sta tus.cfm?show=rereg as of February 18, 2005. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.|USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Chlorpropham (July 2002). EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of February 18, 2005: http://www.epa.gov/pesticides/reregistration/status.htm]

Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)|Combustible under specific conditions. Liquid formulations containing organic solvents may be flammable.

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, and P501|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|Aggregated GHS information provided by 227 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P260, P261, P264, P270, P271, P273, P281, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P312, P314, P321, P337+P313, P391, P405, and P501

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)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec); Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

Extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Carbaryl (agricultural insecticides, nec, liquid); Carbaryl (agricultural insecticides, nec, other than liquid); Carbaryl (insecticides, other than agricultural, nec/|If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos, (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/|Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. 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 carbon columns. /Pesticides/|Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Carbaryl (agricultural insecticides, nec, other than liquid); Carbaryl (insecticides, other than agricultural, nec)/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|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.|Avoid breathing of vapor or spray mist. Use with adequate ventilation. Avoid contact with skin and eyes. ...Keep out of reach of children. Do not use, pour, spill, or store near heat or open flame.

Mild irritant.|Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.

Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.

The substance is mildly irritating to the eyes, skin and respiratory tract.

NO open flames.

Use ventilation (not if powder).

Protective gloves.

Wear safety spectacles.

... ADSORBED READILY TO ORG MATTER IN SOIL. THUS, ORG MATTER CONTENT OF SOIL IS MAJOR CONTROLLING FACTOR IN INFLUENCING DEGREE OF LEACHING WHICH OCCURS. VERY LITTLE ADSORPTION OF CHLORPROPHAM TO MONTMORILLONITE OR KAOLINITE CLAYS OCCURS.

WHEN CLAY GRANULES CONTAINING CHLORPROPHAM WERE APPLIED TO SURFACE OF MOIST SOIL, THE HERBICIDE GRADUALLY MOVED TO THE ATMOSPHERE AS VAPOR & LITTLE ENTERED THE SOIL.

Toxicity

moderately toxic

In order to investigate the various steps of chlorpropham metabolism which could be influenced by cadmium, isolated rat hepatocytes were incubated in the presence of chlorpropham (0.1 mM) and of increasing cadmium concn (0-180 uM). The results showed that cadmium accumulation in hepatocytes was in good correlation to its concn in the incubation medium. At 90 uM cadmium, hydroxylation of chlorpropham was only slightly decreased by 30%, while chlorpropham hydrolysis into 3-chloraniline was unaffected by the presence of cadmium. Accordingly, unchanged chlorpropham increased in hepatocytes. At 27 uM cadmium, free 4-hydroxychlorpropham increased in the intracellular medium as a consequence of a strong suppression of both sulfation and glucuronidation which was related to the strong depletion of the intracellular adenosine triphosphate level under the combined influences of both cadmium and free 4-hydroxychloropropham. Acetylation of 3-chloroaniline, which represents a minor pathway of chlorpropham metabolism, was already markedly suppressed (43%) with the lowest cadmium concn (27 uM). These in vitro results suggest that Phase II reactions are more sensitive to cadmium than Phase I processes and that cadmium enhanced the chloropropham cytotoxicity as shown by alterations of the membrane integrity.

LD50 Rabbit dermal >2000 mg/kg|LC50 Rat oral 1200 mg/kg|LD50 Rat ip 700 mg/kg|LD50 Mouse ip 2600 mg/kg|For more Non-Human Toxicity Values (Complete) data for CHLORPROPHAM (6 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Ataxia, use of wings to aid locomotion from 5th to 8th day after administration of /female mallard ducks, more than 2000 mg/kg orally/|/AQUATIC SPECIES/ Fish were not affected by concn of 5 mg/L.

Chlorpropham's production may result in its release to the environment through various waste streams(SRC); its use as a herbicide and plant growth regulator(1) will result in its direct release to the environment.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 245 to 816(2-5), indicates that chlorpropham is expected to have moderate to low mobility in soil(SRC). Volatilization of chlorpropham from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC),derived from its vapor pressure 1.8X10-4 mm Hg(6) and, water solubility, 89 mg/L(6). Chlorpropham is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.8X10-4 mm Hg(6). The leaching of chlorpropham from three types of soil was low and more than 90% of chlorpropham was found in the upper inch of the soil after 4 cm of rain(7). Depending on the nature of soil and climatic conditions, the field half-lives of chlorpropham in soil range from less than 30 days to 65 days(8) with an average half-life of 30 days(9).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 245 to 816(2-5), indicate that chlorpropham is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(6) based upon an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.8X10-4 mm Hg(7), and water solubility, 89 mg/L(7). According to a classification scheme(8), an estimated BCF of 100(SRC), from its log Kow of 3.51(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Chlorpropham was found to not hydrolyze in aqueous buffer solution at pH 4, 7, and 9(11). Based on a mean rate constant of 2.6X10-14 L/organism-hr and a bacterial concn of 5X10+8 organisms/L in water, the half-life of chlorpropham has been estimated to be 2208 days(12). Therefore, biodegradation of chlorpropham should not be important in clear bodies of water(SRC). However, biodegradation may become important if the bacterial population in water is several orders of magnitude higher than 10+8 organisms(13). The estimated minimum half-life for the direct sunlight photolysis of chlorpropham in clear surface layers of water is 121 days(13). In the concn range 6-7 mg/L, chlorpropham did not metabolize in a river water or in a 2% settled sewage solution(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorpropham, which has a vapor pressure of 1.8X10-4 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chlorpropham 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 9.7 hours (SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chlorpropham does not absorb light with wavelengths >290 nm(4), and is therefore not expected to be susceptible to direct photolysis by sunlight.|MOIST SOIL TREATED WITH CHLORPROPHAM TO GIVE CONCN OF 100 PPM AI WAS INCUBATED IN POLYETHYLENE BAGS @ 23 °C FOR 30 WK. CO2 EVOLUTION WAS DETERMINED WEEKLY. CHLORPROPHAM WAS DEGRADED RAPIDLY IN FIRST 6WK & 5% OF ORIGINAL AMT COULD BE DETECTED 30 WK LATER.

The rate constant for the vapor-phase reaction of chlorpropham with photochemically-produced hydroxyl radicals has been estimated as 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chlorpropham was found to not hydrolyze in aqueous buffer solution at pH 4, 7, and 9(2). The estimated minimum half-life for the direct sunlight photolysis of chlorpropham in a clear water body near the surface is 121 days(3). Chloropropham photolyzed in an aqueous solution when irradiated with 300 nm sunlamps in a Rayonet photoreactor to yield isopropyl 3-hydroxycarbanilate(4,5).

An estimated BCF of 100 was calculated for chlorpropham(SRC), using a log Kow of 3.51(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

398.11 L/kg|Koc values for chlorpropham ranging from 245 to 816 have been reported(1-4). According to a classification scheme(5), these Koc values suggest that chlorpropham is expected to have moderate to low mobility in soil. Leaching of chlorpropham from three different types of soil was low(6). More than 90% of recovered chlorpropham was found in the upper inch of the soil profile after 4 cm of rain(6). Very little chlorpropham adsorbs to montmorillonite or kalonite clay(7).

The Henry's Law constant for chlorpropham is estimated as 5.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.8X10-4 mm Hg(1), and water solubility, 89 mg/L(1). This Henry's Law constant indicates that chlorpropham is expected to be essentially nonvolatile from water surfaces(2). Chlorpropham's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Chlorpropham is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).|AT 35 °C, VAPOR LOSSES OF CHLORPROPHAM FROM DRY SOIL ARE NEGLIGIBLE, BUT INCR TEMP & FIELD MOISTURE CAPACITY GREATLY INCR SUCH LOSSES.

GROUNDWATER: Chlorpropham has been detected in one groundwater sample from 28 of California's 58 counties at a concentration of 8.0 ug/L(1-3). One occurrence of chlorpropham was detected at a concentration of 1.6 ug/L in water samples collected over a one-year period (Mar 1990-Feb 1991) from 240 private wells in rural Illinois(4). Chlorpropham was not detected in the 42 wells sampled in 7 counties of California sampled from July 1994-June 1995(5).|DRINKING WATER: EPA tested water from 783 rural domestic wells and 566 community water system wells nationwide for the presence of various chemicals as part of its 5-year National Survey of Pesticides in Drinking Water Wells; chlorpropham was not detected in this study (minimum reporting limit: 0.35 ug/L)(1).|SURFACE WATER: Chlorpropham was found at concentrations >0.1 ug/L in 43% of freshwater samples collected in 1993 in England and Wales(1).|RAIN/SNOW/FOG: Rainwater was sampled at two locations in the province of South-Holland, The Netherlands in 1997(1). Chlorpropham was detected in 1 of 4 samples collected by an open sampler at the site that is characterized by intensive greenhouse horticultural activities at a concentration of 0.13 ug/L(1). Chlorpropham was detected in 1 of 4 samples in the site that was regarded as a background area at a concentration of 0.06 ug/L(1).

During 1988-1990, chlorpropham was found with a frequency of 3-5% in total diet samples(1-3). The residue level of chlorpropham in post-harvest treated potatoes declined faster when potatoes were stored at room temperature compared to refrigeration(4). During storage at ambient temperature chlorpropham residues dissipated rapidly during the first few days of storage and then at a slower rate(4). This two phase dissipation was not observed for potatoes stored under refrigeration(4). Residue levels declined from 1.81 ppm to 0.6 ppm and 1.3 ppm after 80 days of storage at ambient temperature and at -5 °C, respectively(4). After 6 weeks of storage at -5 °C, potatoes were processed into starch(4). Less than 1% of the initial chlorpropham remained in the starch(4). Pesticide residues were measured in plantbased food in the Belgian total diet from 1991-1993; chlorpropham was found in boiled potatoes at concentrations ranging from 0.5-5.0 mg/kg(5). Chlorpropham was found in 33.3% of sample of fresh potatoes at a mean concentration of 0.553 mg/kg in a monitoring study of fresh vegetables, fruits, and other selected food items in Belgium (1991-93)(6). Detection of chlorpropham was found to occur with a frequency of 4, 4, 4 and 6% in the US FDA Total Diet Study 1982-1984, 1984-1986, 1986-1991 and 1994, respectively(7-9).|Chlorpropham residues in potato chips purchased from supermarkets in Nara, Japan from 1994-1995 ranged from 0.01 to approximately 0.12 mg/kg(1). Chlorpropham was found in 7 of 769 and 28 of 225 samples of fresh potatoes of domestic and imported origin, respectively, in a Canadian study (1992-1994) at concentrations ranging from 0.10 to >2.0 and <0.05 to >2.0 mg/kg, respectively(2). Chlorpropham was detected in 10.3% of potatoes at a mean concentration of 0.12 mg/kg in the 1991-1995 monitoring study of fruits and vegetables from Ontario, Canada(3). In a ten-year accumulated frequency of pesticides and industrial chemicals found in 234 ready-to-eat foods, chlorpropham was detected in 54 foods at an average concentration of 0.1261 mg/kg(4). Chlorpropham residues were reported in 1 of 82 potato samples that were part of the 1996 Danish National Monitoring Program for fruits and vegetables(5).

PUPS OF LACTATING RATS THAT WERE GIVEN LABELLED CHLOROPROPHAM ALSO CONTAINED RADIOACTIVITY.

Occupational exposure to chlorpropham may occur through inhalation and dermal contact with this compound at workplaces where chlorpropham is produced or used. Monitoring data indicate that the general population may be exposed to chlorpropham via ingestion of food. (SRC)|... A day's ration /of potatoes/ for an average adult contains 23 ug of the herbicide chloropropham which is rarely found in other foods.

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)|Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)

After oral or ip administration of (14)C isopropyl and (14)C ring-labelled chloropropham to rats, 4 day urinary excretions were 50 and 85% of dose, respectively for two sites of labelling; in case of isopropyl-labelled compound, an additional 17-20% of dose was excreted as CO2 via lungs. ...When pregnant rats were given (14)C chloropropham, radioactivity was readily transferred to fetuses, and its level did not decline in fetal tissues as rapidly as it did in maternal organs. Pups of lactating rats that were given labelled chloropropham also contained radioactivity.|In Wistar rats given single oral dose of labeled chlorpropham average urinary excretions of radioactivity were 55.9% and 82.6% of chain (14)C CIPC and ring (14)C CIPC. With chain CIPC 35.4 + or - 7.5% of administered dose was excreted in respired air.|Dermal absorption is not significant.|Chlorpropham or its metabolites are readily transported acropetally following root absorption and may be transported basipetally from foliar application in some plants. ...Polar metabolites are not translocated once they are formed in either roots or shoots.|For more Absorption, Distribution and Excretion (Complete) data for CHLORPROPHAM (7 total), please visit the HSDB record page.

In rats, most important metabolic transformation of chloropropham is hydroxylation in the para-position and conjugation of the resulting 4-hydroxychloropropham with sulfate. Hydroxylation of the isopropyl residue accounts for about 1/3 of the metabolism of this herbicide. ...Approximately 4 times more monohydroxy compound than dihydroxy compound were detected. Compound undergoes further oxidation... hydrolytic fission... yields meta-chloroaniline, carbon dioxide and isopropanol, which is further oxidized to acetone and carbon dioxide. Hydroxylation of... meta-chloroaniline also takes place to give N-acetyl-4-amino-2-chlorophenol... plus N-acetyl-2-amino-4-chlorophenol... .|...It was... suggested that chlorpropham... metabolized differently between sensitive and resistant plants. ...Intact carbamates /found/ in sensitive plants... were not observed in resistant plant.|Hydrolysis of carbamate linkage occurred in neomycin treated rats, and in vitro investigation suggested that liver is site of hydrolysis.|Following oral administration... to rats, renal excretion was followed. ...Although the expected hydrolysis products were not found free, n-acetyl hydroxyl analogs were excreted and identified. The 1-carbethoxy compound and a metabolite believed to be 1-hydroxypropyl-2-n-(3-chloro-4-hydroxyphenyl) carbamate was found... after root treatment of soybean plants with CIPC, polar metabolites of CIPC from root and shoot tissues were isolated and purified. Data showed major root metabolite was o-glucoside of 2-hydroxy CIPC. This was also found in shoots... .|For more Metabolism/Metabolites (Complete) data for CHLORPROPHAM (15 total), please visit the HSDB record page.

...The average biological half-life of 14C from both compounds in most organs /of rats administered an oral dose of 14C-labelled propham or chloropropham/ was short, ranging from 3-8 hr. However, in brain, fat, and muscle, the half-life was about twice this value.

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)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other Herbicides/|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. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other Herbicides/

Chlorpropham

Sore throat.


Redness.


Redness. Pain.

Chlorpropham Use and Manufacturing

Methods of Manufacturing

Chloramphenicol can be prepared by the action of 3-chlorophenyl isocyanate and isopropanol. Or made from 3-chloroaniline and isopropyl chloroformate.

Uses

Herbicide; plant growth regulator.

Production

(1975) 4.99X10+8 G (CONSUMPTION)|(1971) 2.25X10+8 g|(1964) 3.00X10+8 g (est)|(1976) GREATER THAN 2.27X10+6 G

Herbicide, of which approximately 82% is used on soybeans and 18% on vegetables (1975)

Emulsifiable concentrates--3 and 4 lb/gal formulations. Granulars--10% and 20% on attapulgite base.|Emulsifiable concentration, dust, solution.|...Formulations include a technical grade (from 98%, to 99% active ingredient (a.i.)), aerosol ready-to-use (RTU) (from 46.5 to 98.7% a.i.), and liquid emulsifiable concentrate (EC), (from 23.8 to 36% a.i.).|Trade and Other Names: Spud Nic, Sprout Nip, Pin Nip, and Decco.

... ANALYZED BY EXTRACTING WITH METHYLENE CHLORIDE & MEASURING BY INFRARED ABSORPTION. ABSORBANCE MEASUREMENTS ARE MADE ON CARBONYL BAND @ 1735/CM, & PERCENTAGE CONCN CALCULATED BY USE OF ABSORBANCE INDEX ESTABLISHED BY MEASUREMENT OF METHYLENE CHLORIDE SOLN CONTAINING STD AMT OF CHLORPROPHAM.|TWO SIMPLE, PRECISE & RAPID REVERSED PHASE HPLC PROCEDURES ARE DESCRIBED FOR DETERMINING CHLOROPROPHAM IN EMULSIFIABLE CONCENTRATES.|GC WITH ECD WAS USED TO DETERMINE CHLORPROPHAM EXTRACTED FROM FRUITS AND VEGETABLES. THE METHOD IS SENSITIVE TO ABOUT 0.2 MG/KG. GC WITH ELECTROLYTIC CONDUCTIVITY DETECTION OF CHLORPROPHAM AFTER ALKYLATION HAS BEEN USED TO DETERMINE CHLORPROPHAM EXTRACTED FROM CROPS @ LIMIT OF DETECTION OF ABOUT 0.005 MG/KG.|THIS PROCEDURE INVOLVES THE DIRECT CONVERSION OF CARBAMATES TO COMPOUNDS AMENABLE TO GC. PENTAFLUOROBENZYL BROMIDE WAS USED AS DERIVATIZATION AGENT FOR CHLORPROPHAM. THERE WAS ONE MINOR PEAK FOR CHLORPROPHAM.|For more Analytic Laboratory Methods (Complete) data for CHLORPROPHAM (15 total), please visit the HSDB record page.

HPTLC and HPLC procedures used for the determination of chlorpropham residues in potatoes.|A simpleand quick GC method for the determination of propham chlorpropham in potatoes.|MICRO-DETERMINATION; IN MILK & URINE FROM DAIRY COWS. EXTRACTION, HYDROLYSIS & SPECTROPHOTOMETRIC TECHNIQUES USING N-1-NAPHTHYLETHYLENEDIAMINE & DETERMINING @ 540 NM.

Agrochemicals -> Herbicides, Plant Growth Regulators|Pharmaceuticals|Herbicides, Plant growth regulators|Environmental transformation -> Pesticides (parent, predecessor)

Chlorpropham has known environmental transformation products that include isopropyl (3-chloro-4-methoxyphenyl)carbamate.

Computed Properties

Molecular Weight:213.66
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:213.0556563
Monoisotopic Mass:213.0556563
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:197
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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