Dichlorprop (ISO)

Dichlorprop

HCID 8427CAS 120-36-5

Grundinformationen

Standard-SMILES
CC(Oc1ccc(Cl)cc1Cl)C(=O)O
InChIKey
MZHCENGPTKEIGP-UHFFFAOYSA-N
Summenformel
C9H8Cl2O3
Durchschnittliche Molmasse
235,06 g/mol
Monoisotopische Masse
233,98504948

Überblick

Yellowish to colorless solid. Soluble in organic solvents. Used as an herbicide.

Namen und Bezeichner

Bevorzugter Name
Dichlorprop
IUPAC
2-(2,4-dichlorophenoxy)propanoic acid
Lokaler Name
Dichlorprop (ISO)
Englischer Name
Dichlorprop
Summenformel
C9H8Cl2O3
Molmasse
235.06

Namen und Synonyme

Dichlorprop120-36-52-(2,4-Dichlorophenoxy)propanoic acid2-(2,4-Dichlorophenoxy)propionic acidDICHLOROPROPHormatoxKildipCelatox-dpHerbizid DPHedonal DPCornox RKSeritox 50
Weitere Namen anzeigen
rd406PATRONU46 DPRD 406PolytoxDROMONEREDIPONWEEDONE
Propanoic acid, 2-(2,4-dichlorophenoxy)-Weedone dp2,4-DPCanapur DPCornoxynilMaycleneWeedone 170Cornox rd

Datenbank-Bezeichner

CAS
120-36-5
PubChem CID
8427
DTXSID
DTXSID0020440
ChEMBL
CHEMBL573221
ChEBI
CHEBI:75370
UNII
J7YV2RKO6Q
EC Number
204-390-5
Nikkaji
J3.254I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
46,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical ClassesCarcinogens
SpringerMaterials PropertiesFusion temperature
Pesticides · 5 Einträge

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Chlorophenoxy

Pesticide (Dichlorprop) -> USDA PDB

Pesticide

LogP · 3 Einträge

log Kow = 3.43

3.43

3.43

Odor · 2 Einträge

ODORLESS

Faint phenolic odor

Density · 2 Einträge

1.42

Relative density (water = 1): 1.4

Physikochemische Eigenschaften

Schmelzpunkt
110 · 110-112 °C(lit.)
Siedepunkt
335.78 °C · 335.78°C (rough estimate)
Dichte
1.3965 · 1.3965 (rough estimate)
Brechungsindex
1.5 · 1.5000 (estimate)
storage temp.
4 °C · APPROX 4°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)

Danger

H302 (98%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

2002/2076

Dichlorprop: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Propanoic acid, 2-(2,4-dichlorophenoxy)-: Environment tier I assessment
DOT LabelClass 9
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards Summary · 1 Eintrag

Decomposed by heat or fire forming toxic and corrosive gases such as phosgene and hydrogen chloride; Can be absorbed through skin; No listed effects of short-term or long-term exposure; May contain carcinogenic impurities; [ICSC] Dichlorprop (racemic mixture) has been replaced commercially by Dichlorprop-p or 2,4-DP-p which contains only the herbicidally active R-isomer (15165-67-0); [HSDB] A skin irritant; May cause serious eye injury; [eChemPortal: ESIS] Chlorophenoxy herbicides are possible human carcinogens; [IARC] Not carcinogenic in rats at up to dietary levels that induce overt toxicity; Not teratogenic at the non-maternotoxic doses tested; No reproductive toxicity identified; [ToxPlanet:CPS&Q: IUCLID] See Dichlorprop-P.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

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

First Aid Measures · 4 Einträge

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer immediately for medical attention.

First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Safe StorageProvision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Separated from food and feedstuffs.
Storage ConditionsIf stored below freezing, /it/ may be necessary to warm to 40 °F and agitate before using.
Cleanup Methods · 1 Eintrag

Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollution Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance contact your State Water Board or Regional Office of the EPA. /Dichlorprop-p/

Toxikologische Informationen

Body Burden · 1 Eintrag

Average concentrations of 1.27 and 3.67 were detected in the urine of workers of a roadside sprayer and a right-of-way sprayer, respectively, exposed to dichlorprop during spray operations in 1980 along an electric power transmission line right-of-way(1). Median urine concentrations of dichlorprop were 0.23 and 0.74 ug/mL in 16 farmers and 6 spraymen exposed to dichlorprop(2).

TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (L346)
Health Effects · 1 Eintrag

It is considered to be a severe eye irritant. There has been concern that chlorophenoxy herbicides including dichlorprop may cause cancer, and in 1987 the International Agency for Research on Cancer (IARC) ranked this class of compounds as group 2B "possibly carcinogenic to humans". The EPA classifies the R-isomer as “Not Likely to be Carcinogenic to Humans.”(L369) Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known human carcinogen. (L177, L178)

Ecotoxicity Values · 5 Einträge

LC50 /Lepomis macrochirus/ (Bluegill sunfish) 165 mg/L/48 hr /Conditions of bioassay not specified/ /Dichlorprop dimethylammonium salt/

LC50 /Lepomis macrochirus/ (Bluegill sunfish) 16 mg/L/48 hr /Conditions of bioassay not specified/ /Dichlorprop isooctyl ester/

LC50 Colinus virginianus (Northern bobwhite, age 14 days) diet 9907 ppm (6938-52102 ppm) for 8 days

LC50 Anas platyrhynchos (Mallard duck, age 14 days) diet >10000 ppm for 8 days

For more Ecotoxicity Values (Complete) data for DICHLOROPROP (19 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 34-129(2), indicate that dichlorprop is expected to have very high to high mobility in soil(SRC). The pKa of dichlorprop is 3.1(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of dichlorprop from moist soil surfaces is not expected to be an important fate process because anions do not volatilize(SRC). Dichlorprop is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.5X10-8 mm Hg(5). Half-lives for the photodegradation of dichlorprop on dry soil ranged from 10 to 19 days(6), increasing to 22 to 59 days for these soils amended with 10% peat(9). Biodegradation half-lives in soil range from 4 days(7) to 124 days(8) and dichlorprop was shown to degrade rapidly after a lag period; the lag period decreased with repeated application and the degradation rate increased with increased pH(9).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 34-129(2) indicate that dichlorprop is expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.1(3) indicates dichlorprop will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of 3.43(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aqueous photodegradation rates of dichlorprop in water from the Danube River, Lake Constance, Kleine Kinzig reservoir, and the Rhine River were 3.02X10-6/sec, 1.54X10-6/sec, 2.81X10-6/sec, and 2.38X10-6/sec, respectively(13), corresponding to half-lives of approximately 3 days, 5 days, and 7 hours, respectively(SRC). Photodegradation products are 6% 2-chlorophenol, 19% 2,4-dichlorophenol, 6% 4-chlorophenol, 6% 2,4-dichlorophenyl acetate, 6% lactone of 2(4-chloro-2-hydroxyphenoxy)propionic acid and 13% 2-(2-chlorophenoxy)propionic acid(12). Several aquatic aerobic studies have reported degradation of dichlorprop in 5 months or less(9-11), indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlorprop, which has a vapor pressure of 7.5X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dichlorprop 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 34 hours(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dichlorprop may be removed from the air by wet or dry deposition(SRC). Dichlorprop contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(4).

Food Survey Values · 1 Eintrag

Dichlorprop was not identified at a concentration above 0.01 mg/kg between 1980 and 1984 in 179 fruit composites Ontario, Canada(1). Dichlorprop was not found at a concentration above 0.01 mg/kg in 354 vegetable composites from Ontario, Canada between 1980 and 1985(2).

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether or not products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing 2,4-DP-p as an active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing 2,4-DP-p. The Agency has determined that 2,4-DP-p-containing products are eligible for reregistration provided that the risk mitigation measures outlined in section C of this document are adopted and label amendments are made to implement these mitigation measures, as outlined in Chapter V.

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. 2-(2,4-Dichlorophenoxy)propionic acid 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: 0294; Pesticide type: herbicide; Registration Standard Date: 09/01/88; Case Status: In Pre-Special Review. The pesticide is in or has completed the reregistration process and, meanwhile, is also the subject of an in-depth Special Review.; Active ingredient (AI): 2-(2,4-Dichlorophenoxy)propionic acid; Data Call-in (DCI) Date(s): 03/03/95; AI Status: Registrants of the pesticide have not made or honored a commitment to seek reregistration, conduct the necessary studies, or pay the requisite fees, or they have asked EPA to cancel their product registrations. Unless some other interested party supports them, products containing the pesticide will be cancelled.

State Drinking Water Guidelines(FL) FLORIDA 35 ug/l

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 3077 9 / PGIII
hs_code
29189990
RTECS-Nr.
UF1050000
risk_code
21/22-38-41-36/37/38-20/21/22

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

2,4-DP-p is thought to increase cell-wall plasticity, biosynthesis of proteins, and the production of ethylene. The abnormal increase in these processes result in abnormal and excessive cell division and growth, damaging vascular tissue. The most susceptible tissues are those that are undergoing active cell division and growth. /2,4-DP-p/

Acts as a selective weedkiller by virture of its plant growth regulating properties.

Metabolism/Metabolites · 4 Einträge

Probably not metabolized by animals.

In plants, metabolism involves degradation of the side-chain to 2,4-dichlorophenol, ring hydroxylation, and ring opening.

Degradation products of 2,4-DP-p include 2,4-dichlorophenol, 2,4- dichloroanisole, and carbon dioxide, which are all common degradates to 2,4-D. /2,4-DP-p/

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing CDDs induce both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. (L177)

Absorption, Distribution and Excretion · 5 Einträge

Dermal absorption can occur on prolonged contact of the soln with the skin ... .

Absorbed by the leaves, with translocation to the roots.

Dichlorprop ... has been detected in the urine of exposed farmers and spraymen.

... (14)C-2,4-DP-p ( ... purity 99.3% ai; (phenyl-U-(14)C)-labeled) was admin to Wistar rats (5/sex/dose) via gavage at a single dose of 5 or 100 mg/kg or a single dose of 5 mg/kg following a 14-day pretreatment with unlabeled 2,4-DP-p at 5 mg/kg/day. For each dosing regimen, (14)C-2,4-DP-p was readily absorbed by rats following oral dosing with max plasma concn being attained within 2 to 5 hr of dosing. The total recovery of dosed radioactivity was 91 to 100% within 120 hr of oral dosing at 5 mg/kg as either a single dose or a single dose following pretreatment ... The total recovery of dosed radioactivity was 100 to 102% within 168 hr of oral dosing at 100 mg/kg. For all three dosing regimens, 87 to 96% of the dose was recovered in urine, cage washing, and cage debris. Fecal elimination accounted for 4 to 12% of the dose. There were no apparent differences in elimination between the sexes or among the groups. The levels of radioactivity in tissues were insignificant. Following a single dose of (14)C-2,4-DP-p at 5 mg/kg, a mean peak plasma concn was calculated to be 19.4 and 26.2 ug equiv/g for male and female rats, respectively. A peak plasma concn was reached in 2.4 and 2.7 hr for male and female rats, respectively. The mean t1/2 of elimination was 4.4 hr (male) and 14.8 hr (female). The area under concentration vs time curve (AUC) value was 114 and 130 ug equiv hr/g for male and female rats, respectively. Plasma concn in male and female rats declined rapidly during the first 24 hr and thereafter plasma concn in both sexes were negligible. Following a single dose of (14)C-2,4-DP-p at 100 mg/kg, a mean peak plasma concn was calculated to be 412 and 425 ug equiv/g for male and female rats, respectively. A peak plasma concn was reached in 5.4 and 4.2 hr for male and female rats, respectively. The mean t1/2 of elimination was 16.5 hr (male) and 6.6 hr (female). The AUC value was 9655 and 6109 ug equiv hr/g for male and female rats, respectively. Plasma concn in male and female rats declined rapidly during the first 24 and 48 hr, respectively and thereafter plasma concn declined slowly. In both male and female rats 1 hr after dosing, plasma (26 to 27 ug/g), blood (15 to 16 ug/g), heart (7 to 8 ug/g), lung (6 to 9 ug/g), liver (7 to 8 ug/g), kidney (29 to 34 ug/g), thyroid (17 to 37 ug/g), and adrenals (7 ug/g) contained relatively higher concn of radioactivity. In female rats, gonads (10 ug/g) and uterus (8 ug/g) also contained higher concn of radioactivity. All other tissues contained less than 5 ug equiv/g. The levels of radioactivity at 3 hr after dosing in male and female rats were comparable to the levels at 1 hr after dosing. The levels of radioactivity in most tissues at 6 hr after dosing were less than the levels at 1 hr after dosing. The results of the TLC and HPLC analyses on pooled urine (0 to 6 hr) from Groups A, B and C showed that the majority of the admin dose in the urine samples was identified as unchanged parent cmpd which represented 14.11 to 32.6, 6.16 to 24.8 and 1.68 to 5.65% of the admin dose in dose groups A, B and C, respectively. The chromatograms from 6 to 12 and 12 to 24 hr pooled urine samples showed parent cmpd only. In the 0 to 6 hr urine samples, there were up to 5 minor unknown components but none of them accounted for more than 1% of the admin dose. The results of the HPLC analyses of 0 to 24 hr fecal samples (groups A and B) and 0 to 48 hr fecal samples (group C) showed that the major component in the feces was identified as unchanged parent cmpd. The amt of unchanged parent eliminated in the feces represented 2 to 7% of the admin dose in dose groups A, B and C. In the 0 to 24 hr fecal samples, there were up to 5 minor unknown components but none of them accounted for more than 1% of the admin dose. /2,4-DP-p/

For more Absorption, Distribution and Excretion (Complete) data for DICHLOROPROP (6 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

Used as post-emergence herbicide for control of annual and perennial broad-leaved weeds in cereals, turf, rangeland, public easements, aquatic areas, and other non-crop land; Also used to prevent premature fruit drop in apples; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For dichloroprop (USEPA/OPP Pesticide Code: 031401) 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./

When used as directed at 2.5 lb per acre controls Polygonum persicaria, Polygonum lapathifolium, Polygonum convolvulus and Spergula arvensis in addition to many of the weeds controlled by mecoprop.

Herbicide plant growth regulator /for/ brush control on rangeland, rights-of-way, aquatic weeds. /It is used for/ control of polygonum species, calium aparine (cleavers), chickweed, in cereals, pastures, turf, alone or mixed with other hormone type phenoxy herbicides (e.g.,MCPA).

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3259]
Methods of ManufacturingDichlorprop may be made by: (a) condensation of 2-chloropropionic acid with 2,4-dichlorophenol or (b) chlorination of 2-phenoxypropionic acid.
Formulations/Preparations · 5 Einträge

Invert emulsion of butoxyethanol, ester, aqueous solution of (potassium or amine salt), and emulsifiable concentrate of isooctyl and butoxyethanol esters (600-720 g/L), soluble concentrates (600-720 g/L).

Soluble concentrate of alkali metal or amine salts; 'Polyclene', (dichlorprop-potassium); emulsifiable concentrate of esters; emulsifiable concentrate based on dried non-hygroscopic salts. Mixtures include: 'Basagran DP' (BAS 35 801H), soln (260 g bentazone + 340 g ai dichlorprop-ethylammonium/l). ... 'Certrol PA', dichlorprop + ioxynil + MCPA. ... 'Cornoxynil', dichlorprop-(iso-octyl) + bromoxynil octanoate. ... 'Herbitox', (dichlorprop + benazolin + dicamba, as alkali metal salts). 'Mayclene', (dichlorprop + chlopyralid + MCPA). 'Oxytril P', (dichlorprop-(iso-octyl) + bromoxynil octanoate + ioxynil octanoate). 'Tetroxone M', liquid (dichlorprop + bromoxynil + ioxynil + MCPA). 'Ustilan NK25', dichlorprop + amitrole + ethidimuron.

WEEDONE 2,4-DP, WEEDONE 170, & ENVERT 171 (MIXTURES OF 2,4-D & 2,4-DP ESTERS); CORNOX RK 64; CORNOX RK EXTRA CONCENTRATE (2,4-DP & MCPA); TRI-CORNOX SPECIAL (2,4-DP WITH BENAZOLIN & DICAMBA); DICHLORPROP (TECH)

Soluble concentrate; emulsifiable concentrate

For more Formulations/Preparations (Complete) data for DICHLOROPROP (9 total), please visit the HSDB record page.

Household ProductsInformation on 1 consumer products that contain 2-(2,4-Dichlorophenoxy)propionic acid in the following categories is provided:
General Manufacturing Information · 6 Einträge

Propanoic acid, 2-(2,4-dichlorophenoxy)-: ACTIVE

Exists in two optically active forms; only the (+)-isomer shows biological activity.

In Canada dichlorprop is used in combination with 2,4-D acetic acid ... Canadian Patent 736, 882.

USUAL CARRIER: WATER AT NOT LESS THAN 225 L/HA.

DICHLORPROP IS A POST-EMERGENCE TRANSLOCATED HERBICIDE ... USED AT 2.7 KG AE/HA AND MAY BE USED ALONE OR IN COMBINATION WITH OTHER HERBICIDES.

For more General Manufacturing Information (Complete) data for DICHLOROPROP (9 total), please visit the HSDB record page.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

常州帝通化工有限公司+86-0519-88298848 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An aromatic ether that is 2-hydroxypropanoic acid in which the hydroxy group at position 2 has been converted to its 2,4-dichlorophenyl ether.

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