イソプロピル－Ｎ－（３－クロロフェニル）カーバメート

Pesticide -> EPA IRIS

Herbicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Herbicides, Plant growth regulators

Environmental transformation -> Pesticides (parent, predecessor)

log Kow= 3.51

3.4

3.42

Faint characteristic odor

Very faint odor

1.18 at 86 °F (NTP, 1992) - Denser than water; will sink

1.180 at 30 °C

1.18 g/cm³

Colorless solid

Light-tan powder

Light brown crystalline solid

less than 1 mg/mL at 64 °F (NTP, 1992)

Readily soluble in most organic solvents (e.g., alcohols, ketones, esters, chlorinated hydrocarbons, aromatic hydrocarbons); moderately soluble in mineral oils (100 g/kg kerosene)

Miscible in acetone, carbon disulfide; very soluble in anhydrous ammonia, aromatic solvents, ethyl and isopropyl alcohol, ketones; soluble in kerosene or diesel oil

In water, 89 mg/L at 25 °C

Solubility in water, g/100ml: 0.009 (very poor)

477 °F at 760 mmHg (decomposition) (NTP, 1992)

149 °C at 2 mm Hg

Boiling point: 246 °C with decomposition

When heated to decomposition it emits highly toxic fumes of /hydrogen chloride, nitrogen oxides and phosgene/.

247 °C

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P260, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.4% (1 of 71) of reports.

Warning

H351 (98.6%): Suspected of causing cancer [Warning Carcinogenicity]

Commission Regulation No 844/2012

Chlorpropham is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

04/20/EC, Reg. (EU) 2017/841, Reg. (EU) 2018/917, Reg. (EU) 2019/989, Reg. (EU) No 540/2011

Chlorpropham: HSNO Approval: HSR002826 Approved with controls

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.

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]

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. Chlorpropham is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0271; Pesticide type: Herbicide; Registration Standard Date: 12/31/87; Case Status: RED Approved 09/95; 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): Chlorpropham; Data Call-in (DCI) Date(s): 04/01/94, 12/03/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Tolerances are established for residues of the plant regulator and herbicide CIPC (isopropyl m- chlorocarbanilate) and its metabolite 1-hydroxy-2-propyl 3'-chlorocarbanilate (calculated as CIPC) in or on the following raw agricultural commodities: potato, postharvest.

While petitions for tolerances for negligible residues are pending and until action is completed on these petitions, interim tolerances are established for residues of the listed pesticide chemicals in or on the following raw agricultural commodities: milk; meat, fat, and meat byproducts of cattle, hog, horse and sheep 0.05 ppm.

There are four Special Local Needs [24(c)] registrations. They are for use on Easter lilies (on approximately 150 acres annually in Oregon and California), on gingko trees in Washington, DC, and on post-harvest stored potatoes growing in high humidity conditions in the state of Maine which requires a higher application rate.

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.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

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.

Give one or two glasses of water to drink.

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.

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)/

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

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.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

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. Chlorpropham is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0271; Pesticide type: Herbicide; Registration Standard Date: 12/31/87; Case Status: RED Approved 09/95; 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): Chlorpropham; Data Call-in (DCI) Date(s): 04/01/94, 12/03/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Tolerances are established for residues of the plant regulator and herbicide CIPC (isopropyl m- chlorocarbanilate) and its metabolite 1-hydroxy-2-propyl 3'-chlorocarbanilate (calculated as CIPC) in or on the following raw agricultural commodities: potato, postharvest.

While petitions for tolerances for negligible residues are pending and until action is completed on these petitions, interim tolerances are established for residues of the listed pesticide chemicals in or on the following raw agricultural commodities: milk; meat, fat, and meat byproducts of cattle, hog, horse and sheep 0.05 ppm.

There are four Special Local Needs [24(c)] registrations. They are for use on Easter lilies (on approximately 150 acres annually in Oregon and California), on gingko trees in Washington, DC, and on post-harvest stored potatoes growing in high humidity conditions in the state of Maine which requires a higher application rate.

(FL) FLORIDA 1,400 ug/L

(CA) CALIFORNIA 1200 ug/L

...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.

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 carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

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.

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.

Used as a herbicide to control many annual grassy and broadleaf weeds in alfalfa, lima and snap beans, blueberries, cane berries, cranberries, carrots, ladino clover, garlic, seed grass, peas, onions, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli, and woody nursery stock; Also used to inhibit potato sprouting and for systemic sucker control in tobacco; [HSDB]

For chloropropham (USEPA/OPP Pesticide Code: 018301) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Chlorpropham acts as highly selective preemergence and early postemergence herbicide; it effectively controls many annual grassy and broadleaf weeds; application during late fall and winter for control of some perennial weeds.

For control of weeds in alfalfa, lima and snap beans, blueberries, cane berries, cranberries, carrots, ladino clover, garlic, seed grass, peas, onions, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli, woody nursery stock. Also for inhibiting potato sprouting and systemic sucker control in tobacco.

Chlorpropham is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

(1975) 3.0X10+6 G (PRINCPL CUSTOMS DISTS)

(1976) 1.00X10+6 G (PRINCPL CUSTMS DISTS)

(1975) 4.99X10+8 G (CONSUMPTION)

(1971) 2.25X10+8 g

(1976) GREATER THAN 2.27X10+6 G

Reaction of 3-chlorophenyl isocyanate with isopropyl alcohol. ... Lab method of purification: recrystallize from n-hexane.

... Reaction of 3-chloroaniline with isopropyl chloroformate.

Preparation: E. D. Witman, US 2695225; Strain, US 2734911 (1954, 1956 both to Columbia-Southern Chem.); Brockway, US 2806051 (1957 to B. F. Goodrich)

Emulsifiable concentrates--3 and 4 lb/gal formulations. Granulars--10% and 20% on attapulgite base.