Chlorpropham Chemical Properties

Melting point:

41°C

Boiling point:

247°C

Density 

1.18

refractive index 

nD20 1.5388

Flash point:

247°C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

crystalline

pka

13.06±0.70(Predicted)

color 

light tan

Odor

faint char. odor

Water Solubility 

0.009 g/100 ml very poor

Decomposition 

247 ºC

Merck 

14,2187

BRN 

2211397

Exposure limits

An experimental carcinogen and neoplastigen

Stability:

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

CAS DataBase Reference

101-21-3(CAS DataBase Reference)

IARC

3 (Vol. 12, Sup 7) 1987

NIST Chemistry Reference

Chlorpropham(101-21-3)

EPA Substance Registry System

Chlorpropham (101-21-3)

Safety Information

Hazard Codes 

Xn,N,F

Risk Statements 

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

Safety Statements 

61-36/37-26-16

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

FD8050000

HS Code 

2924.29.4300

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

101-21-3(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1.2 g/kg (Boyd, Carsky)

MSDS

• Language:English Provider:Isopropyl 3-chlorocarbanilate
• Language:English Provider:SigmaAldrich

Chlorpropham Usage And Synthesis

Physicochemical properties

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 melting point is 38.5 ~ 40℃. Stable at lower than 100 C, but slowly hydrolyzed in acid and alkaline medium.

Toxicity

The acute oral administration of LD50 is 5 ~ 7.5g/kg in rats, and the acute oral administration is 5g/kg in rabbits. The drug had no toxic effect on rabbit skin for 20 hours or 2g/ kg feed for rats and dogs for 2 years. The acute oral administration is LD50>2g/kg for wild ducks. The TLm (48 hours) of goldfish and carp (48 hours) is 10 ~ 40mg/L.

Mechanism of action

Mitotic inhibitor, in many perennial crops and some annual crops, it can be used alone or with other herbicides as pre-emergent selective weed removal. It is a plant growth regulator as well as a herbicide. It inhibits the activity of beta amylase, inhibits the synthesis of RNA and protein, interferes with oxidative phosphorylation and photosynthesis, and destroys cell division. Chloraniline is volatile. The steam can be absorbed by the bud in order to suppress weed bud growth. The residual effect in soil was longer than that of aniline, and the selectivity for some crops was smaller than that of aniline. In addition, it also regulates the growth of plants. It is used to inhibit the germination of potatoes during storage, flower and fruit thinning etc..

Applicable crops

Alfalfa, wheat, corn, soybean, sunflower, potato, sugar beet, rice, carrots, spinach, onions, etc..

Prevention and control object

Annual grasses and certain broadleaf weeds including ryegrass, barnyard grass, bluegrass, purslane, chickweed and Tusizi etc. annual grasses and certain broadleaf weeds.

Usage method

The amount of effective components is 2.24 ~ 4.5kg per hectare per hectare below 16 C in pre seedling soil treatment. Double the amount above 24 centigrade and mix soil after application. The post seedling treatment is 1.2 ~ 3.5kg. For the post seedling treatment, the activity of herbicide is poor. But it can control amaranth and Polygonum, chickweed and purslane in the seedling. As a growth regulator, it is used to inhibit the germination of potatoes.

Preparation method

It can be made by reaction of inter - Chloroaniline and isopropyl chloroformate or isopropanol and ISO - chlorophenyl isocyanate.

Analysis method

Determine the CO2 produced by acidolysis.
Residue determination:
(1) The H2SO4 is hydrolyzed of 1:1 by the extraction of two hydrogen methane, and the alkali is obtained. The 3- hydrogen aniline is vaporized and the colorimetric determination is carried out by the hypochlorite - phenol method.
(2) Infrared spectroscopy.

Chemical Properties

beige to brown solid

Uses

Preemergent and postemergent herbicide used to regulate plant growth and control of weeds in carrot, onion, garlic and other crops

Uses

Chlorpropham is particularly useful in agricultural settings. It is used in pesticide products for treatment of plants and soil.

Uses

Herbicide; plant growth regulator.

Definition

ChEBI: A carbamate ester that is the isopropyl ester of 3-chlorophenylcarbamic acid.

General Description

Brown chunky solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chlorpropham 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.

Hazard

Toxic by ingestion.

Fire Hazard

Flash point data for Chlorpropham are not available, however Chlorpropham is probably combustible.

Agricultural Uses

Herbicide, Plant growth regulator: Chlorpropham is a plant growth regulator that is used primarily in the U.S. to inhibit post-harvest potato sprouting. Other uses include pre-emergence control of grass weeds in alfalfa, beans, blueberries, cane berries, carrots, cranberries, ladino clover, garlic, seed grass, onions, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli and woody nursery stock. It is used to control suckers in tobacco

Trade name

ATLAS® CIPC 40; BEET-KLEEN® (with Fenuron® and isopropyl carbanilate); BUDNIP®; CAMPBELL’S® CIPC 40%; CHLORO IPC®; ELBANIL®; FASCO® WY-HOE; FURLOE®; FURLOE® 4EC; JACK WILSON® CHLORO 51 (OIL); LIRO METOXON®; MIRVALE®; MORCRAN® (with n-1-naphthylphthalamic acid); MSS® CICP; NEXOVAL®; PREVENOL® 56; PREVENTOL®; PREVENTOL® 56; PREWEED®; RESIDUREN®; RESIDUREN® EXTRA; SPROUT NIP®; SPROUT-NIP® EC; SPUDNIC®; SPUD-NIE®; STOPGERME®-S; TATERPEX®; TRIPEC® (with carbamic acid, phenyl-, 1-methylethyl ester); TRIHERBICIDE® CIPC; UNICROP® CIPC; WAREFOG®; Y3®

Environmental Fate

Soil. Hydrolyzes in soil forming 3-chloroaniline (Bartha, 1971; Hartley and Kidd, 1987; Smith, 1988; Rajagopal et al., 1989). In soil, Pseudomonas striata Chester, a Flavobacterium sp., an Agrobacterium sp. and an Achromobacter sp. readily degraded chlorpropham to 3-chloroaniline and 2-propanol. Subsequent degradation by enzymatic hydrolysis yielded carbon dioxide, chloride ions and unidentified compounds (Kaufman, 1967; Rajagopal et al., 1989). Hydrolysis products that may form in soil and in microbial cultures include N-phenyl-3-chlorocarbamic acid, 3-chloroaniline, 2-amino-4-chlorophenol, monoisopropyl carbonate, 2-propanol, carbon dioxide and condensation products (Rajagopal et al., 1989). The reported half-lives in soil at 15 and 29°C are 65 and 30 days, respectively (Hartley and Kidd, 1987)
Plant. Chlorpropham is rapidly metabolized in plants (Ashton and Monaco, 1991). Metabolites identified in soybean plants include isopropyl-N-4-hydroxy-3-chlorophenylcarbamate, 1-hydroxy-2-propyl-3′-chlorocarbanilate and isopropyl-N-5-chloro-2-hy
Photolytic. The photodegradation rate of chlorpropham in aqueous solution was enhanced in the presence of a surfactant (TMN-10) (Tanaka et al., 1981). In a later study, Tanaka et al. (1985) studied the photolysis of chlorpropham (50 mg/L) in aque
Chemical/Physical. Emits toxic phosgene fumes when heated to decomposition (Sax and Lewis, 1987). In a 0.50 N sodium hydroxide solution at 20°C, chlorpropham was hydrolyzed to aniline derivatives. The half-life of this reaction was 3.5 days (El-Dib and Aly, 1976). Simple hydrolysis leads to the formation of 3-chlorophenylcarbamic acid and 2-propanol. The acid is very unstable and is spontaneously converted to 3-chloroaniline and carbon dioxide (Still and Herrett, 1976)

Chlorpropham(101-21-3)Related Product Information

• 2,4-Dichloroaniline
• Allyl chloroformate
• 2,5-Dichloroaniline
• ISOPROPYL LAURATE
• Isopropyl chloroformate
• Formic acid isopropyl ester
• 2-Chloroaniline
• 3,4-Dichloroaniline
• DIALLYL ISOPHTHALATE
• 3-Chloroaniline
• Diisopropyl azodicarboxylate
• 4-Chloroaniline
• 2,6-Dichloroaniline
• Diallyl phthalate
• 2'-Hydroxy-3-phenylpropiophenone
• Isopropyl alcohol
• DICHLORPHENAMIDE BULK POWDER
• CHLORBUFAM