5836-10-2CC(C)OC(=O)C(O)(c1ccc(Cl)cc1)c1ccc(Cl)cc1AXGUBXVWZBFQGA-UHFFFAOYSA-NChloropropylate is a tertiary alcohol, an isopropyl ester, an organochlorine acaricide and a member of monochlorobenzenes. It has a role as a bridged diphenyl acaricide. It is functionally related to a 4,4'-dichlorobenzilic acid.
5836-10-2DTXSID5041778CHEMBL1552611CHEBI:39411Acaricides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organochlorine Pesticides
WHITE POWDER
Colorless crystals.
At 20 °C: 700 g/L acetone, dichloromethane; 50 g/L hexane; 300 g/L methanol; 130 g/L n-octanol; 500 g/L toluene
In water, 10 mg/L @ 20 °C.
73 °C
MP: 66-72 °C /Technical product/
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.
Danger
H318 (92.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.
49 216 72; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, nec, other, than agricultural).
49 216 73; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, agricultural, nec, other than 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)./
... 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.
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.
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Wird geladen…
0.00000018 [mmHg]
1.8X10-7 mm Hg @ 20 °C
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.
UN 2761; Organochlorine pesticides, solid, toxic, not otherwise specified (compounds & preparations)
UN 2762; Organochlorine pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C (compounds & preparation)
UN 2995; Organochlorine pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint 23 °C or more
UN 2996; Organochlorine pesticides, liquid, toxic, not otherwise specified
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for CHLOROPROPYLATE (6 total), please visit the HSDB record page.
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/
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.
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/
LC50 Rainbow trout 0.45 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LC50 Goldfish 0.6 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LC50 Bluegill 0.66 mg/L/96 hr /Conditions of bioassay not specified in source examined/
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).
/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.
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).
/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 is metabolized by a yeast, Rhodotorula gracilis, in two major reaction steps, an initial hydrolytic process and a subsequent decarboxylation-dehydrogenation to form 4,4'-dichlorobenzophenone and CO2(1). Following a 10 day period, the percent distribution of metabolites was 94.4% chloropropylate, 1.7% 4,4'-dichlorobenzilic acid, 0.6% 4,4'-dichlorobenzophenone, and 3.4% unknown metabolites; after 20 days, 84.4% was chloropropylate, 0.2% 4,4'-dichlorobenzilic acid, 11.6% 4,4'-dichlorobenzophenone and 3.6% unknown metabolites(1). After an 8 week incubation period, a small amount of chloropropylate still existed in solution(2).
AEROBIC: Aerobic biodegradation data for chloropropylate are lacking. However, biodegradation data for the structurally analogous compound chlorobenzilate have been found. Chlorobenzilate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). Chlorobezilate underwent 29-40% primary degradation at a concentration of 0.0022 ppm in Cayuga, Cayuta, and Seneca Lakes (New York State Finger Lakes Region, US) water grab samples after 22 days(2). This substance underwent 52, 88, and 92% primary degradation at concentrations of 2, 0.072, and 0.0032 ppm, respectively, in Beebe Lake (Ithaca, New York) water grab samples after 22 days. Chlorobenzilate underwent 12 and 14% primary degradation at 3 ppm in Green Lake and Wai-Shuang River (Taipei Prefecture, Taiwan) water grab samples, respectively(3). This substance underwent 82% degradation after 21 days in a Lukang silty clay loam grab sample from Chang-Hwa Prefecture, Taiwan and 40% degradation after 21 days in a Pincheng clay grab sample from Taipei Prefecture, Taiwan(3). The chemical concentration in both of these samples was 0.0022 ppm. The rate of loss of chlorobenzilate at 0.25, 0.50, and 1 ppm in Leon fine sand grab samples were 12, 59, and 77%, respectively, after 56 days(4). The rate of loss of chlorobenzilate at 0.25, 0.50, and 1 ppm in lakeland fine sand grab samples were 50, 74, and 88%, respectively, after 56 days. Leon fine sand has a higher organic content than Lakeland soil. Based on the behavior of the structurally analogous compound chlorobenzilate in these grab sample tests, chloropropylate is expected to biodegrade in water and soil(SRC).
ANAEROBIC: Chloropropylate may be resistant to anaerobic biodegradation since it is stable in ruminal fluid(1).
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 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).
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of 5 male and 5 female rats dosed orally by intubation 6 times weekly for 4 weeks with 50, 250 or 500 mg/kg/day chloropropylate suspended in gum arabic failed to show any toxic effects as judged by changes in survival, body-weight gain and microscopic examination of tissues after autopsy. Administration over 12 weeks of 0, 100, 1000, 5000 and 25,000 ppm of chloropropylate in the diet to groups of 21 male and 21 female rats resulted in a mortality of 29% at the 5,000 ppm level and 70% at the 25,000 ppm level. At the highest level, hair loss occurred after 2 weeks, and bloody nasal discharge was frequently observed. Body-weight gain was doubtfully depressed in males at 1000 ppm and definitely depressed in both sexes at higher dose levels. Food intake levels were reduced in both sexes at 25,000 ppm. Histopathological examination of tissues revealed dose related changes in the liver, and an increasing incidence of testicular atrophy at doses of 1000 ppm and above.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Dichlorbenzilic acid, was fed to groups of 20 male and 20 female rats for 99 days at dose levels of 0, 20, 100, 500 and 2500 ppm active ingredient in a 20% powder. Food consumption body-weight gain, mortality, organ weights and gross and histopathology showed no significant changes from the controls. A tendency to slight depression of kidney and testes weight was noted at 2500 ppm. /Dichlorbenzilic acid (metabolite)/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Administration over 3 months of 0, 100, 500 or 3000 ppm of chloropropylate in a dry diet to groups of 3 male and 3 female dogs resulted in slight depression of average bodyweight gain in male dogs at 3000 ppm. Hematology, biochemical studies, urinalysis, gross and histopathology were all comparable to controls. Organ to body-weight ratios were increased in the case of liver and kidney at 3000 ppm in both sexes.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ A 1-yr interim report of a 2-yr feeding study using chloropropylate 40% wettable formulation in groups of 3 male and 3 female dogs at 0, 100, 500 and 3000 ppm active ingredient indicates some depression of female growth rate in 2 out of 3 female dogs at 500 ppm. At 3000 ppm, body-weight loss or insufficient gain (5 out of 6) gastric stress and trauma (5 out of 6), elevated alkaline phosphatase (4 out of 4, day 90), and mortality (3 out of 6) occurred. The survivors were reduced to an intake of 2000 ppm after 104 days and were taken off the test at the 116th day. They were again dosed with 2000 ppm from the 198th day of the study. After one year, this 2000 ppm group showed no adverse effect, except slightly high urinary albumin in one male and one female animal.
For more Non-Human Toxicity Excerpts (Complete) data for CHLOROPROPYLATE (7 total), please visit the HSDB record page.
... 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.
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.
Used as non-systemic contact acaricide for cotton, fruit, nuts, vegetables, and ornamentals; Also used as marine anti-fouling agent; [HSDB]
No longer registered as a pesticide for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
For chloropropylate (USEPA/OPP Pesticide Code: 026801) there are 0 labels match. /SRP: Not registered for current 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./
Non-systemic contact acaricide; discontinued in 1978
Marine anti-fouling agent.
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.
VerwendenChloropropylate is a dichlorobenzylic acid derivative and a related compound of DDT. Chloropropylate is an aracicide used for mite control.