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Pindone

HCID 6732
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
83-26-1
Standard SMILES
CC(C)(C)C(=O)C1C(=O)c2ccccc2C1=O
InChIKey
RZKYEQDPDZUERB-UHFFFAOYSA-N
Molecular formula
C14H14O3
Average molar mass
230.26 g/mol
Monoisotopic mass
230.0942943

Overview

Pindone appears as yellow solid or powder. (NTP, 1992)

Names & identifiers

Preferred name
Pindone
IUPAC
2-(2,2-dimethylpropanoyl)indene-1,3-dione
English name
PINDONE
Molecular formula
C14H14O3
Molecular weight
230.26

Names & synonyms

PINDONE83-26-12-Pivaloyl-1,3-indandioneChemratPivalylPivalynPivalPivalyl ValoneTri-BanPivaldionePindonPivacin
Show more names
PIVAL(R)
2-Pivaloylindane-1,3-dionePivaldion2-Pivalyl-1,3-indandioneParacakes1,3-Indandione, 2-pivaloyl-Contrax-PPara-Pac2-Pivaloyl-indan-1,3-dion

Database identifiers

CAS
83-26-1
PubChem CID
6732
DTXSID
DTXSID1025930
ChEMBL
CHEMBL1369243
ChEBI
CHEBI:82261
UNII
2KFI1XBH7G
EC Number
201-462-8
Nikkaji
J4.628K

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
51.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
17
Formal charge
0
Complexity
351

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
PesticidesPesticides -> Rodenticides, Anticoagulant
OdorAlmost no odor.
TasteTASTELESS
Density · 5 items

1.06 (NIOSH, 2024) - Denser than water; will sink

1.06

1.06 g/cm³

1.06

1.06

Color/Form · 4 items

Yellow crystals

Bright yellow crystals from ethanol

Bright yellow powder

Yellow-brown cystalline solid

Solubility · 6 items

less than 1 mg/mL at 72 °F (NTP, 1992)

SOL IN ALCOHOL, ETHER, ACETONE, AQ ALKALI SOLN

Readily soluble in aq alkali or ammonia to give bright yellow salts

Soluble in most organic solvents

In water, 18 mg/l @ 25 °C

Solubility in water at 25 °C: none

Boiling Point · 4 items

Decomposes (NIOSH, 2024)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P273, P301+P316, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P273, P301+P316, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationPindone: HSNO Approval: HSR002775 Approved with controls
Other Safety InformationIMAP assessments - 1H-Indene-1,3(2H)-dione, 2-(2,2-dimethyl-1-oxopropyl)-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2 items

Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)

Combustible.

Health HazardsExcerpt from NIOSH Pocket Guide for Pindone:
Hazards SummaryA vitamin K antagonist that inhibits prothrombin; [ACGIH]
Reactive GroupKetones
EC ClassificationSymbol: T, N; R: 25-48/25-50/53; S: (1/2)-37-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III

Chemistry & industry

Pharmacology

Mechanism of Action · 3 items

Pindone is a vitamin K antagonist, with delayed inhibition of prothrombin formation, and repeated doses have a cumulative effect on blood coagulation. Death in animals from chronic exposure is due to multiple internal hemorrhage.

These compounds depress the hepatic synthesis of vitamin K1-dependent clotting factors (II, VII, IX, X) by inhibiting the vitamin K1 2,3-reductase enzyme in the vitamin K1-epoxide cycle. /Anticoagulant rodenticides/

Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins ...in the coagulation cascade... are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase... . The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

180 °C @ 1 MM HG

decomposes

Decomposes

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 5 items

227.3 to 230.9 °F (NTP, 1992)

108.5-110.5 °C

108-110 °C

230 °F

230 °F

Vapor Pressure · 5 items

Very low (NIOSH, 2024)

1 mm Hg @ 180 °C

Vapor pressure at 25 °C: negligible

Very low

Very low

Physical Description · 5 items

Pindone appears as yellow solid or powder. (NTP, 1992)

Bright-yellow powder with almost no odor. [rodenticide]; [NIOSH]

YELLOW CRYSTALS.

Bright-yellow powder with almost no odor.

Bright-yellow powder with almost no odor. [rodenticide]

Physicochemical properties

Melting point
108 · 108-110°
Boiling point
312.25 °C · 312.25°C (rough estimate)
Density
1.1914 · 1.1914 (rough estimate)
refractive index
1.5557 · 1.5557 (estimate)
storage temp.
20 °C · APPROX 20°C
solubility
Soluble in most organic solvents (Worthing and Hance, 1991)
pka
3.47 · 3.47±0.10(Predicted)
color
Bright yellow crystals
Water Solubility
18 ppm · 18 ppm at 25 °C (Gunther et al., 1968)
Merck
13 · 13,7526
BRN
2051258 · 2051258
Henry's Law Constant
1.1 · 1.1×106 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits
0.1 mg/m3OSHA:PEL-TWA · ACGIH:TLV-TWA 0.1 mg/m3OSHA:PEL-TWA 0.1 mg/m3NIOSH:REL-TWA 0.1 mg/m3
Major Application
agricultureenvironmental
InChI
1S/C14H14O3/c1-14(2,3)13(17)10-11(15)8-6-4-5-7-9(8)12(10)16/h4-7,10H,1-3H3
InChIKey
RZKYEQDPDZUERB-UHFFFAOYSA-N
SMILES
CC(C)(C)C(=O)C1C(=O)c2ccccc2C1=O
EWG's Food Scores
1 · 1
FDA UNII
2 KFI1XBH7G · 2KFI1XBH7G
EPA Substance Registry System
Pindone (83-26-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06,GHS08,GHS09
Signal word
Danger
Hazard statements
301 · H301-H372-H410
Precautionary statements
264 · P264-P270-P260-P273-P301+P310-P330-P314-P391-P405-P501
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T,N
Risk Statements
25 · 25-48/25-50/53
Safety Statements
37 · 37-45-60-61
RIDADR
3027 · 3027
OEB
D
OEL
0.1 mg/m3 · TWA: 0.1 mg/m3
WGK Germany
3 · 3
RTECS
6300000 · NK6300000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29143990 · 29143990
Storage Class
6.1 C · 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 1 Oral
Hazardous Substances Data
83 · 83-26-1(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in male rats: 280 mg/kg (Gaines)
IDLA
100 mg/m3 · 100 mg/m3
Special Reports · 1 item

USEPA; Reregistration Eligibility Decision Document - Rodenticide Cluster. Washington, DC: USEPA, Off Pest Prog. USEPA 738-R-98-007 July 1998. Available from the Database Query page at http://www.epa.gov/REDs/ as of March 17, 2003. The Reregistration Eligibility Decision (RED) contains the Agency's evaluation of the data base of this chemical, its conclusions of the potential human health and environmental risks of the current product uses, and its decisions and conditions under which these uses and products will be eligible for reregistration.

FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Pivalyl-1,3-indandione is found on List B. Case No: 2810; Pesticide type: Rodenticide; Case Status: OPP has made a decision that products containing the pesticide are not eligible for reregistration.; Active ingredient (AI): 2-Pivalyl-1,3-indandione; Data Call-in (DCI) Date(s): 06/17/91; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

OSHA StandardsPermissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.1 mg/cu m.

Safety & protection

Fire Fighting · 2 items

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

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

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 a slurry of activated charcoal in water to drink. Refer for medical attention .

First Aid · 2 items

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.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs.
Fire Fighting Procedures · 1 item

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 foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

Cleanup Methods · 1 item

1. VENTILATE AREA OF SPILL. 2. FOR SMALL QUANTITES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). 2. LARGE QUANTITIES MAY BE RECLAIMED; HOWEVER, IF THIS IS NOT PRACTICAL, DISSOLVE IN FLAMMABLE SOLVENT (SUCH AS ALC) & ATOMIZE IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 3 items

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

1. BY MAKING PACKAGES OF PIVAL IN PAPER OR OTHER FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 2. BY DISSOLVING PIVAL IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

Incineration: Dissolve it in a flammable solvent and spray into the fire chamber.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Preventive Measures · 5 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

IN EMERGENCIES DURING MFR OR USE WHEN THERE MAY BE DANGER OF HEAVY EXPOSURE, SUITABLE RESP PROTECTIVE EQUIPMENT SHOULD BE WORN TO PREVENT DUST FROM ENTERING MOUTH. PERSONAL HYGIENE ... PRACTICED TO ENSURE THAT FOOD EATEN BY PEOPLE ... DOES NOT BECOME CONTAMINATED. /COUMARIN & INDANDIONE DERIV/

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.

Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear safety spectacles.

Toxicology

Interactions · 4 items

FACTORS THAT MAY ENHANCE TOXICITY OF ANTICOAGULANT RODENTICIDES INCL...PRESENCE OF DRUGS (PHENYLBUTAZONE, OXYPHENBUTAZONE, DIPHENYLHYDANTOIN, SALICYLATES) THAT DISPLACE ANTICOAGULANT FROM PLASMA ALBUMIN...ADMIN OF ADRENOCORTICOTROPIC HORMONE (ACTH), STEROIDS, OR THYROXIN, WHICH MAY INCR RECEPTOR SITE AFFINITY FOR ANTICOAGULANT... /ANTICOAGULANT RODENTICIDES/

IS SYNERGISTIC WITH ALLETHRIN & PYRETHRIN.

The following drugs ... may increase ... response to coumarin or indandione derivatives: alcohol (acute intoxication), allopurinol, aminosalicylic acid, amiodarone, anabolic steroids, chloral hydrate, chloramphenicol, cimetidine, clofibrate, co-trimoxazole, danazol, dextrothyroxine sodium, diazoxide, diflunisal, disulfiram, erythromycin, ethacrynic acid, fenoprofen calcium, glucagon, ibuprofen, indomethacin, influenza virus vaccine, isoniazid, meclofenamate, mefenamic acid, methylthiouracil, metronidazole, miconazole, nalidixic acid, neomycin (oral), pentoxifylline, phenylbutazone, propoxyphene, propylthiouracil, quinidine, quinine, salicylates, streptokinase, sulfinpyrazone, sulfonamides, sulindac, tetracyclines, thiazides, thyroid drugs, tricyclic antidepressants, urokinase, vitamin E. /Coumarin & indandione derivatives/

The following drugs ... may ... decrease ... response to coumarin or indandione derivatives: alcohol (chronic alcoholism), barbiturates, carbamazepine, corticosteroids, corticotropin, ethchlorvynol, glutethimide, griseofulvin, mercaptopurine, methaqualone, oral contraceptives containing estrogen, rifampin, spironolactone, vitamin K. /Coumarin & indandione derivatives/

Target OrgansBlood prothrombin
Ecotoxicity Values · 4 items

LC50 Mallard duck oral 250 mg/kg/8 days

LC50 Bobwhite quail oral 1,560 mg/kg/8 days

LC50 Bluegill sunfish 1.6 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Rainbow trout 0.21 mg/l/96 hr /Conditions of bioassay not specified/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a water solubility of 18 mg/l(2) and a regression-derived equation(3), indicates that pindone is expected to have low mobility in soil(SRC). Volatilization of pindone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.3X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Pindone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.4X10-6 mm Hg(SRC), determined from a fragment constant method(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a water solubility of 18 mg/l(2) and a regression-derived equation(3), indicates that pindone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.3X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 120(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pindone, which has an estimated vapor pressure of 8.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pindone 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 6 days(SRC), calculated from its rate constant of 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase pindone may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 items

The substance can be absorbed into the body by ingestion.

inhalation, ingestion

Ecotoxicity Excerpts · 2 items

/BIRDS and MAMMALS/ The sensitivity of a number of avian species to the rabbit poison pindone was investigated using increase of prothrombin time (PT) as an index of poisoning. Daily dose levels of pindone were 0.25 mg kg-1 for eagles, 4.0 mg kg-1 for magpies and 5.0 mg kg-1 for pigeons, parrots and ducks. Considerable species variation in response was observed, and within each species there was considerable individual variation in response to pindone. The PTs of magpies and ducks increased to approximately twice baseline levels. Significant elevations (4- to 7-fold) occurred in parrots, pigeons and eagles. Clinical symptoms were observed in only one species, the wedge-tailed eagle. Results of our dosing trials indicate that all species tested are theoretically at risk of pindone poisoning, although the risk to some species is minimized by factors such as population size, food availability and bait placement.

/OTHER TERRESTRIAL SPECIES/ ... It is important to note that rodenticides and other vertebrate pesticides, such as ... pindone, are widely used in Australia to control introduced mammalian pests. Unintentional exposure of native marsupial fauna to these compounds may result in detrimental effects and pose a threat to some species and populations. ...Possum /are/ less susceptible than eutherians /to/ pindone. /from table/

Signs and Symptoms · 2 items

Spontaneous bleeding from various sites.

epistaxis (nosebleed), excess bleeding from minor cuts, bruises; smoky urine, black tarry stools; abdominal, back pain

ICSC Environmental Data · 1 item

The substance is very toxic to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to birds and mammals. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

Soil Adsorption/Mobility · 1 item

The Koc of pindone is estimated as 900(SRC), using a water solubility of 18 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pindone is expected to have low mobility in soil.

Human Toxicity Excerpts · 5 items

/HUMAN EXPOSURE STUDIES/ Acute clinical effects depend on the site of hemorrhage & include hemoptysis, hematuria, gastrointestinal bleeding, abdominal or back pain (retroperitoneal hemorrhage), hemarthrosis, epistaxis, cerebrovascular accidents, & multiple ecchymotic lesions. /Anticoagulant rodenticides/

/HUMAN EXPOSURE STUDIES/ The usual mode of death is gastrointestinal hemorrhage. /Anticoagulant rodenticides/

/HUMAN EXPOSURE STUDIES/ /Indandione deriv/ ... can produce hemorrhagic accidents if they are absorbed in large or repeated quantities, or by persons with natural or acquired sensitivity. /indandione deriv/

/HUMAN EXPOSURE STUDIES/ If accidental ingestion occurs, the symptoms and signs are anticipated to be similar to those caused by warfarin, which may include hematuria, spontaneous hematomas on the arms and legs, epistaxis, bleeding from the lips, punctate hemorrhages from mucous membranes, abdominal and back pain, vomiting, blood in the feces, petechial rash, and abnormal blood findings, such as increased prothrombin time and blood plasma, blood in urine and feces, and hypochromic and microcytic anemia.

For more Human Toxicity Excerpts (Complete) data for PINDONE (8 total), please visit the HSDB record page.

Artificial Pollution Sources · 1 item

Pindone's former production and use first as an insecticide and rodenticide(1) may have resulted in its direct release to the environment(SRC). The USEPA has ruled that all uses of pindone and its sodium salts are ineligible for reregistration as the manufacturer did not submit required data to continue this product's registration(2).

Regulatory information

FIFRA Requirements · 1 item

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Pivalyl-1,3-indandione is found on List B. Case No: 2810; Pesticide type: Rodenticide; Case Status: OPP has made a decision that products containing the pesticide are not eligible for reregistration.; Active ingredient (AI): 2-Pivalyl-1,3-indandione; Data Call-in (DCI) Date(s): 06/17/91; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Safety data

OEB
D
OEL
TWA: 0.1 mg/m3
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
IDLA
100 mg/m3
tsca
TSCA listed
rtecs
NK6300000
ridadr
3027
hs_code
29143990
Toxicity
LD50 orally in male rats: 280 mg/kg (Gaines)
risk_code
25-48/25-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS08,GHS09
hazard_code
T,N
safety_code
37-45-60-61
hazard_class
6.1(b)
Storage Class
6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H301-H372-H410
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 1 Oral
Precautionary statements
P264-P270-P260-P273-P301+P310-P330-P314-P391-P405-P501
Hazardous Substances Data
83-26-1(Hazardous Substances Data)
Biological Half-LifeThe half time for absorption after oral administration was about 2.3 hours. The average half time for elimination was 110.8 hours for oral and 90.9 hours for iv dosing.
Absorption, Distribution and Excretion · 5 items

... THEY ARE NOT ABSORBED BY LUNGS & THEY DO NOT PENETRATE THE SKIN. /1,3-INDANDIONE DERIV/

ANTICOAGULANT RODENTICIDES ARE ABSORBED SLOWLY BUT FAIRLY COMPLETELY FROM INTESTINAL TRACT. IN BLOODSTREAM, THESE COMPD ARE BOUND TO LARGE EXTENT TO PLASMA ALBUMIN. BOUND POISON IS NOT ACTIVE, BUT EXTENT OF BINDING CAN BE DECR BY OTHER DRUGS & POSSIBLY BY SUBSTANCES ... RELEASED DURING STRESS. /ANTICOAGULANT RODENTICIDES/

AFTER SINGLE DOSE WAS ADMIN TO DOGS, 67% PIVAL WAS ABSORBED & EXCRETION WAS EXTREMELY SLOW WITH T/2 OF NEARLY 5 DAYS, DUE TO STRONG BINDING TO CANINE PLASMA PROTEIN, HIGH LIPOPHILITY & LACK OF TRANSFORMATION TO POLAR METABOLITES. DOGS WERE ADMIN A SINGLE DOSE OF 3 OR 5 MG/KG BY CAPSULE OR IV. PLASMA CONCN INCR RAPIDLY FROM ABOUT 4 MUG/ML 30 MIN AFTER ORAL ADMIN TO MAX OF OVER 10 MUG/ML AFTER 13 HR. IT DECLINED IN A LOGARITHMIC LINEAR MANNER AFTER ORAL & IV ADMIN. HIGHEST CONCN WAS 11.3 MUG/ML IN THE BLOOD OF A DOG THAT DIED 132 HR AFTER ORAL ADMIN OF 5 MG/KG. LOWEST CONCN FOUND IN THIS DOG WAS 0.7 MUG/ML IN THE BRAIN.

ANALYSIS SHOWED THAT PINDONE PASSED THROUGH THE PLACENTAL BARRIER OF A PREGNANT DOG & THE CONCENTRATION WAS HIGHER IN THE PUPPIES THAN IN THE MOTHER SUGGESTING AN INABILITY OF THE PUPPIES TO METABOLIZE OR ELIMINATE THE PINDONE.

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

Uses & manufacturing

Uses · 6 items

Used as an anticoagulant rodenticide and an insecticide; [ACGIH]

Farming (Pesticides) [Category: Industry]

For pindone (USEPA/OPP Pesticide Code: 067703) 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./

Pharmaceutical intermediate; insecticide; rodenticide.

Was originally suggested as a substitute for the greater part of the pyrethrins in pyrethrum sprays ... it is used as an anticoagulant rodenticide in baits containing 250 mg/kg

Control of rats and mice. Bait shyness does not occur after feeding. Renders cereal bait resistant to insect infestation and fungal infection.

U.S. Production · 2 items

(1972) LESS THAN 4.54X10+4 GRAMS (USE)

(1975) PROBABLY GREATER THAN 9.1X10+5 GRAMS

Consumption PatternsLESS THAN 4.54X10+4 GRAMS USED FOR AGRICULTURAL PURPOSES (1971)
Methods of Manufacturing · 2 items

Reaction of ethyl phthalate with pinacolone.

Produced by condensation of diethyl phthalate with 3,3-dimethylbutanone using sodium in benzene as condensing agent... .

Formulations/Preparations · 4 items

Marketed as 0.2% or 0.5% powder and mixed 1 part with 19 parts of bait material. Small amount of edible oil up to 5% prevents dusting and increased acceptability. Pival at concentrations of 0.025% in cereal bait will kill rats.

Mixed formulations: (pindone +) warfarin

Pival CB (5 g active ingredient/kg) powder for use in rat baits; Pivalyn, (pindone-sodium with chelating agent)

Pivalyn (sodium salt)

General Manufacturing Information · 6 items

1H-Indene-1,3(2H)-dione, 2-(2,2-dimethyl-1-oxopropyl)-: ACTIVE

The WHO Recommended Classification of Pesticides by Hazard identifies Pindone (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

Introduced by Kilgore Chem Co (US PATENT 2310949) as trade marks 'Pivalyl volone', 'Pival', 'Pivalyn'... .

Baits should be placed in areas inaccessible to children, pets, wildlife, and domestic animals or in tamper-proof bait boxes. ...Rodents do not develop bait shyness after feeding. Imparts to cereal baits resistance to both insect infestation and molds. Controls Norway rats, roof rats, and house mice.

Suggested for use to replace greater part of pyrethrins in fly sprays... .

For more General Manufacturing Information (Complete) data for PINDONE (6 total), please visit the HSDB record page.

Applications · 3 items

UsesInsecticide; rodenticide

UsesPindone may be used as an analytical reference standard for the quantification of the analyte in biological samples using different chromatography techniques.

General DescriptionYellow solid or powder.

Suppliers19 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
南通合润生物科技有限公司18362409333 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
天津荣燊化工有限公司18317763565; 18317763565 · [email protected]
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
深圳利斯康医药科技有限公司+86-755-89396905 +86-15013857715 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
南通众合化工新材料有限公司0513-85666561 15950816326 · [email protected]

Additional notes

DefinitionChEBI: Pindone is a member of indanones and a beta-triketone.