Chloropropylate
-
Chloropropylate
structure -
-
CAS No:
5836-10-2
-
Formula:
C17H16Cl2O3
-
Chemical Name:
Chloropropylate
-
Synonyms:
Benzeneacetic acid,4-chloro-α-(4-chlorophenyl)-α-hydroxy-,1-methylethyl ester;Benzilic acid,4,4′-dichloro-,isopropyl ester;ENT 26999;Isopropyl 4,4′-dichlorobenzilate;Acaralate;Chloropropylate;Rospin;Rospine
- Categories:
-
CAS No:
Description
Chloropropylate is an organochlorine acaricide, a member of monochlorobenzenes, a tertiary alcohol and an isopropyl ester. It has a role as a bridged diphenyl acaricide. It derives from a 4,4'-dichlorobenzilic acid.
Chloropropylate Basic Attributes
339.21
339.21
227-421-4
GI03ROM7HQ
DTXSID5041778
WHITE POWDER|Colorless crystals.
29181990
Characteristics
46.5
4.18090
1.36 g/cm3 @ Temp: 20 °C
73 °C
148-150 °C @ Press: 0.5 Torr
230.6ºC
1.578
In water, 10 mg/L @ 20 deg C.
1.8X10-7 mm Hg @ 20 deg C
Oral-Rat LD50: 5000 mg/kg; Oral-Mouse LD50: 5000 mg/kg
Combustion produces toxic chloride gas
Henry's Law constant = 8.03X10-9 atm-cu m/mol @ 25 °C /Estimated/
Hydroxyl radical reaction rate constant = 6.87X10-12 cu cm/molecule-sec @ 25 °C /Estimated/
Safety Information
NONH for all modes of transport
41
26-39
DD2450000
Xi
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Unstable in alkaline media and strongly acidic media
P280-P305 + P351 + P338
H318
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.
FAO/WHO; Evaluation of the Toxicity of Pesticide Residues in Food: Chloropropylate (1969). Available from: http://www.inchem.org/documents/jmpr/jmpmono/v068pr09.htm as of July 13, 2004.
|Danger|H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/
If material on fire or involved in 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. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: 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. /Organochlorine pesticides, solid, toxic/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Toxicity
moderately toxic
LD50 Rat oral 5000 mg/kg|LD50 Mouse oral 5000 mg/kg|LD50 Rabbit dermal 10.2 g/kg|LD50 Chicken oral 2500 mg/kg
/BIRDS and MAMMALS/ No deaths resulted when mallard ducks were fed diets containing 0.8% chloropropylate for seven days, although reduced food consumption and body-weight occurred at this dose level.|/BIRDS and MAMMALS/ Bobwhite quail were fed for 7 days on diets containing 0.8, 0.4 and 0.2% chloropropylate. The LD50 was about 0.4% and reduced food intake and weight loss were apparent in all groups.
Chloropropylate's former production and use(1) as an acaricide(2) may have resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a water solubility of 10 mg/L(2) and a regression-derived equation(3), indicates that chloropropylate is expected to have low mobility in soil(SRC). Volatilization of chloropropylate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant estimated as 8.03X10-9 atm-cu m/mol(SRC) derived from its vapor pressure, 1.80X10-7 mm Hg(4), and water solubility(2). Chloropropylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.80X10-7 mm Hg(4). The structurally analogous compound chlorobenzilate underwent 40 and 82% degradation in soil grab samples after 21 days(5). The rate of loss of chlorobenzilate in fine sand grab samples ranged from 12 to 88% after 56 days(5). Based on the behavior of this structurally similar compound, biodegradation of chloropropylate in soil may be an important environmental fate process.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a water solubility of 10 mg/L(2) and a regression-derived equation(3), indicates that chloropropylate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a an estimated Henry's Law constant estimated as 8.03X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.80X10-7 mm Hg(4), and water solubility(2). According to a classification scheme(5), an estimated BCF of 170(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The structurally analogous compound chlorobenzilate underwent 29-40 and 52-92% primary degradation at concentrations of 0.0022 and 2-0.0032 ppm, respectively in water samples collected from lakes in the New York Finger Lakes Region(7). Based on the behavior of this structurally similar compound, chloropropylate is expected to biodegrade in water.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloropropylate, which has a vapor pressure of 1.80X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chloropropylate 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 23 hours(SRC), calculated from its rate constant of 6.87X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase chloropropylate may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of chloropropylate with photochemically-produced hydroxyl radicals has been estimated as 6.87X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chlorpropylate is stable to hydrolysis at neutral pH but less stable under alkaline and acid conditions(2). Chloropropylate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).
An estimated BCF of 170 was calculated for chloropropylate(SRC), using a water solubility of 10 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).
The Koc of chloropropylate is estimated as 1200(SRC), using a water solubility of 10 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chloropropylate is expected to have low mobility in soil(SRC).
The Henry's Law constant for chloropropylate is estimated as 8.03X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 1.80X10-7 mm Hg(1), and water solubility, 10 mg/L(2). This Henry's Law constant indicates that chloropropylate is expected to be essentially nonvolatile(3). Chloropropylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Chloropropylate was detected in domestic and import commodities at unreported concentrations during a 4 year study of pesticides in food(1).
Occupational exposure and general population exposure to chloropropylate in the United States is expected to be low or non-existent since chloropropylate is no longer produced or used in the US. (SRC)
Drug Information
In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/|Metabolic studies extending over 10 days were performed on pairs of dogs (one male and one female) treated orally with technical chloropropylate at 12.8 or 64.1 mg/kg on five consecutive days. Urinary excretion accounted for 5.2 and 33.2% of the total dose in the urine of the males at low and high dose levels, the corresponding figures for the female being 3.2 and 33.7%. In the feces, 6.4 and 3.4% were detected in the male, at low and high doses respectively, and 16.9 and 7.3% in the female. No residues were detected in blood, brain, fat, liver, kidney or muscle at sacrifice. The method of analysis employed would not detect dichlorobenzilic acid conjugates. The presence of the probable metabolite, dichlorobenzilic acid has been demonstrated in dog urine, by thin layer chromatography.|When (14)carbon-labelled chloropropylate was administered orally to pairs of male and female rats at about 1.6 mg/kg the radioactivity was excreted in the urine and feces. No radioactive carbon dioxide was expired. The excretion pattern of the radioactivity differed between the two sexes, the male voiding 75% of the dose in the feces, and 6% in the urine, and the female 49% in the feces and 31% in the urine. Most of the radioactivity was eliminated in the first 48 hours. The total tissue residue of radioactivity 120 hours after administration was 0.9% and 1.0% in the male and female respectively. The majority of these residues were in the liver and fat.|When chloropropylate was fed to cow, major route of elimination was via urine (more than 80% of total dose). ... Chloropropylate was stable (up to 7 hr) in rumen fluid but decomposed in 10,000xg supernatant fraction of beef liver.|For more Absorption, Distribution and Excretion (Complete) data for CHLOROPROPYLATE (6 total), please visit the HSDB record page.
When chloropropylate was fed to cow, major route of elimination was via urine (more than 80% of total dose). About 28% of material was identified as 4,4'-dichlorobenzilic acid and 55% as conjugates, not further identified. ... Spider mites and house flies ... metabolized chloropropylate to corresponding chlorine-containing analogs of benzilic acid, benzhydrol, benzophenone, and benzoic acid.|... Chlorobenzilate (CB), chloroprppylate (CP), orbromopropylate (BP). Samples were incubated aerobically for 4 hours in flasks in a water bath at 37 degrees-C. Major metabolites from degradation were identified by cochromatography. The metabolites were subjected to infrared analysis and mass spectrometry. CB, CP, and BP were degraded by the rat liver preparations; however, CB was metabolized appreciably more than the other two acaricides. The maximum activity with CB was associated with the nuclear supernatant and the microsomal fractions. The major degradation products were 4,4'-dichlorobenzophenone (DBP) and p-chlorobenzoic-acid (CBA). For CP, the nuclear and mitochondrial fractions were the most active. The major metabolite was DBP. More than 93 percent of remained after 4 hours of incubation. p-Bromobenzoic-acid BP was the major metabolite.|... Rats fed C-14 chloropropylate in a single dose at level simulating a dietary intake of 35 ppm were found to eliminate three radioactive components in the urine and feces. ... No respired radioactivity could be demonstrated. Analysis of internal organs resulted in the recovery of significant amounts of radioactivity in the kidney, liver, heart, stomach contents, and gastrointestinal tract.|... Three identified metabolites resulting from the degradation of /chloropropylate/, were 4,4'-dichlorobenzilic acid, 4,4'-dichlorobenzophenone, and carbon dioxide.|For more Metabolism/Metabolites (Complete) data for CHLOROPROPYLATE (6 total), please visit the HSDB record page.
... DDT, DDE, TDE, Kelthane, chlorobenzilate, chloropropylate and Acarol were found to be inhibitory towards both heavy beef heart mitochondrial (HBHM) NADH-oxidase and succinoxidase enzyme systems. Dichlorobenzophenone and p-chlorophenol were less inhibitory towards the HBHM NADH-oxidase and did not inhibit the succinoxidase enzyme system. DDA did not inhibit either of the electron transport systems. Carbaryl was not inhibitory towards both HBHM oxidase systems, whereas its degradative product dihydroxynaphthalene was inhibitory at the same concentration. Furadan, Matacil, Baygon and Dimetilan were only slightly inhibitory towards the mitochondrial NADH-oxidase system and did not inhibit the succinoxidase system. Zectran was inhibitory towards the NADH-oxidase system and was not inhibitory towards the succinoxidase system. DDT, DDE and TDE, dihydroxynaphthalene and 1-naphthol inhibited the NADH-oxidase enzyme system on the substrate side of cytochrome c, whereas Kelthane inhibited on the oxygen side.
Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposed occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. ... /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/|In patients who have been poisoned by organochlorine contamination of skin, clothing, hair and/or eyes, decontamination must proceed concurrently with whatever resuscitative and anticonvulsive measures are necessary to preserve life. Contamination of the eyes should be removed by flushing with copious amounts of clean water. If the pesticide-exposed person remains alert and physically able, a prompt shower and shampoo may be appropriate, provided the patient is carefully observed to insure against sudden appearance of poisoning. If there are any indications of weakness, ataxia, or other neurologic impairment, clothing should be removed and a complete bath and shampoo given while the victim is recumbent, using copious amounts of soap and water. Attendants should wear rubber gloves. Surgical green soap is excellent for this purpose, but ordinary soap is about as good. The possibility of pesticide sequestered under fingernails or in skin folds should not be overlooked. Contaminated clothing should be promptly bagged and not returned until it has been thoroughly laundered. Contaminated leather shoes should be discarded. The possibility that pesticide has contaminated the inside surfaces of gloves, boots, and headgear should be considered. /Solid organochlorine insecticides/|If organochlorine has been ingested in a quantity sufficient to cause poisoning, the stomach and intestine must be emptied, and measures taken to limit toxicant absorption. Because seizure activity may develop rapidly, lavage, with a large bore orogastric tube and with rigorous protection of the airway, is probably preferable to induced emesis in most cases. If the victim is convulsing, it is almost always necessary first to control seizures before attempting gastric intubation. The effectiveness of lavage in removing pesticide from the stomach diminishes rapidly with the passage of time. Particularly in poisoning by large doses of organochlorine, monitor pulmonary ventilation carefully to forestall respiratory failure. Assist pulmonary ventilation mechanically with oxygen whenever respiration is depressed. /Solid organochlorine insecticides/|For more Antidote and Emergency Treatment (Complete) data for CHLOROPROPYLATE (6 total), please visit the HSDB record page.
/SIGNS AND SYMPTOMS/ Organochlorines are CNS stimulators that produce apprehension, excitability, paresthesias, dizziness, headache, disorientation, and tremor progressing to stupor, coma, and convulsions in severe cases. Organochlorines may enhance myocardial irritability, leading to cardiac dysrhythmias after heavy exposures. Serious complications involve seizures with resultant hypoxemia, severe metabolic acidosis, and death. Intoxication from acute oral exposures generally begins within 45 minutes to several hours. Subacute toxicity has been reported after the extensive and careless use of chlordane over several weeks. Symptoms included paresthesias, anorexia, nausea, fatigue, and malaise. /Organochlorines/|/SIGNS AND SYMPTOMS/ The chief toxic action of the organochlorine pesticides is on the central nervous system, where these compounds interfere with fluxes of cations across nerve cell membranes, increasing neuronal irritability. This effect is manifest mainly as convulsions, sometimes limited to myoclonic jerking, but often expressed as violent seizures. ... Convulsions may cause death by interfering with pulmonary gas exchange and by generating severe metabolic acidosis. Various disturbances of sensation, coordination, and mental function are also characteristic of acute organochlorine poisoning. High tissue concentrations of organochlorines increase myocardial irritability, predisposing to cardiac arrhythmias. When tissue organochlorine concentrations drop below threshold levels, recovery from the poisoning occurs. Organochlorines are not cholinesterase inhibitors. /Solid organochlorine insecticides/|/EPIDEMIOLOGY STUDIES/ ... A statistically significant increased risk was found for self-reported exposure to ethylan (1,1-dichloro-2,2-bis(4-methoxyphenyl) ethane). Increased odds ratios were observed for self-reported exposures to chloropropylate and DDT, as well as for the summary group of organochlorine pesticides which included all of these materials, though these associations were not significant.
chloropropylate
Chloropropylate Use and Manufacturing
Chloropropylate is made by reacting 4,4'-dichlorobenzilic acid with isopropanol.
Chloropropylate is a dichlorobenzylic acid derivative and a related compound of DDT.Chloropropylate is an aracicide used for mite control.
Rospin 25% emulsifiable soln; 50% wettable powder (50 wp); gesakur 25% emulsifiable concentrate.|Technical product is at least 90% pure ...
The WHO Recommended Classification of Pesticides by Hazard identifies Chloropropylate (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Used to control spider mites on apple and pear trees. /Former use/|.../Chloropropylate is/ suitable for use at 30-60 g ai/100 L on cotton, fruit, nuts, ornamentals, sugar beet, tea and vegetables, applied to obtain full coverage of foliage. It is non-phytotoxic at these rates.|Contact, non-systemic acaricide for control of adult mites; effective against summer eggs and against all postembryonic stages.|For more General Manufacturing Information (Complete) data for CHLOROPROPYLATE (7 total), please visit the HSDB record page.
PRODUCT ANALYSIS IS BY GAS LIQUID CHROMATOGRAPHY. RESIDUES MAY BE DETERMINED BY GLC WITH MICROCOULOMETRIC DETECTION.|A GAS CHROMATOGRAPHIC METHOD FOR DETERMINING CHLOROPROPYLATE AS A TRIFLUOROACETYL DERIVATIVE WAS EXAMINED. RECOVERY FROM FORTIFIED SAMPLES OF STRAWBERRY, CITRUS, & OTHER SAMPLES RANGED FROM 79-89%. GAS CHROMATOGRAPH COLUMN WAS COMPOSED OF 5% DEGS.|Method: 8081A, Organochlorine Pesticides by Gas Chromatography; Analyte: chloropropylate; Matrix: extracts from solid and liquid matrices; Detection Level: not provided.[
Agrochemicals -> Acaricides
Computed Properties
Molecular Weight:339.2
XLogP3:4.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:338.0476498
Monoisotopic Mass:338.0476498
Topological Polar Surface Area:46.5
Heavy Atom Count:22
Complexity:348
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Latest News on Chloropropylate
- The project with an investment of ¥105 million and an annual output of 4000 tons of Propargite is to be built
- Nichino Mexico promotes a new Tolfenpyrad insecticide in Mexico
- Agri Technology Asia(2024) will be held in Lahore from July 27-29
- Bayer: Revenue of 13.765 billion euros( Q1)was in line with expectations
- IHARA plans to launch seven new solutions in Brazil by 2024
Learn More Other Chemicals
-
Deltamethrin
52918-63-5
-
Cypermethrin
86753-92-6
-
Chlorindan
57-74-9
-
S-Bioallethrin Formula
28434-00-6
-
Fenothiocarb1 Formula
62850-32-2
-
Dicyclanil Formula
112636-83-6
-
1,3-Difluoro-2-propanol Structure
453-13-4
-
Naled Structure
300-76-5
-
What is N,N-Diethyl-m-toluamide
134-62-3
-
What is Oxamyl
23135-22-0