Bromadiolone

Last updated
Bromadiolone
Bromadiolon Grundstruktur V2.svg
Names
IUPAC name
3-[3-[4-(4-Bromophenyl)phenyl]-3-hydroxy-1-phenylpropyl]-2-hydroxychromen-4-one
Other names
Broprodifacoum; Bromatrol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.044.718 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1/C30H23BrO4/c31-23-16-14-20(15-17-23)19-10-12-22(13-11-19)26(32)18-25(21-6-2-1-3-7-21)28-29(33)24-8-4-5-9-27(24)35-30(28)34/h1-17,25-26,32-33H,18H2
    Key: OWNRRUFOJXFKCU-UHFFFAOYSA-N
  • Brc1ccc(cc1)c2ccc(cc2)C(O)CC(C\3=C(/O)c4ccccc4OC/3=O)c5ccccc5
Properties
C30H23BrO4
Molar mass 527.414 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Warning label on a tube of rat poison containing bromadiolone on a dike of the Scheldt river in Steendorp, Belgium Rattenvergifwaarschuwing edit.JPG
Warning label on a tube of rat poison containing bromadiolone on a dike of the Scheldt river in Steendorp, Belgium

Bromadiolone is a potent anticoagulant rodenticide. It is a second-generation 4-hydroxycoumarin derivative and vitamin K antagonist, often called a "super-warfarin" for its added potency and tendency to accumulate in the liver of the poisoned organism. When first introduced to the UK market in 1980, it was effective against rodent populations that had become resistant to first generation anticoagulants.

Contents

The product may be used both indoors and outdoors for rats and mice.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. [1]

Toxicity

Paste contains bromadiolone (0.005%) Bromadiolone paste.jpg
Paste contains bromadiolone (0.005%)

Bromadiolone can be absorbed through the digestive tract, through the lungs, or through skin contact. The pesticide is generally given orally. [2] The substance is a vitamin K antagonist. The lack of vitamin K in the circulatory system reduces blood clotting and will cause death due to internal hemorrhaging. [2]

Poisoning does not show effects for 24 to 36 hours after it is eaten and can take up to 2–5 days to cause death.[ clarification needed ]

Following are acute LD50 values for various animals (mammals): [2]

Chemistry

The compound is used as a mixture of four stereoisomers. Its two stereoisomeric centers are at the phenyl- and the hydroxyl-substituted carbons in the carbon chain of the substituent at the 3 position of the coumarin.

Bromadiolone
(R,S)-Bromadiolon V1.svg
(1R,3S)-isomer
(S,R)-Bromadiolon V1.svg
(1S,3R)-isomer
(R,R)-Bromadiolon V1.svg
(1R,3R)-isomer
(S,S)-Bromadiolon V1.svg
(1S,3S)-isomer

Antidote

Vitamin K1 is used as antidote. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Warfarin</span> Anticoagulant medication

Warfarin, sold under the brand name Coumadin among others, is an anticoagulant medication. While the drug is described as a "blood thinner", it does not reduce viscosity but rather inhibits coagulation. Accordingly, it is commonly used to prevent blood clots in the circulatory system such as deep vein thrombosis and pulmonary embolism, and to protect against stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Less commonly, it is used following ST-segment elevation myocardial infarction (STEMI) and orthopedic surgery. It is usually taken by mouth, but may also be administered intravenously. It is a vitamin K antagonist.

<span class="mw-page-title-main">Chlorfenvinphos</span> Chemical compound

Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.

<span class="mw-page-title-main">Ethion</span> Chemical compound

Ethion (C9H22O4P2S4) is an organophosphate insecticide. It is known to affect the neural enzyme acetylcholinesterase and disrupt its function.

<span class="mw-page-title-main">Rodenticide</span> Chemical used to kill rodents

Rodenticides are chemicals made and sold for the purpose of killing rodents. While commonly referred to as "rat poison", rodenticides are also used to kill mice, woodchucks, chipmunks, porcupines, nutria, beavers, and voles. Despite the crucial roles that rodents play in nature, there are times when they need to be controlled.

<span class="mw-page-title-main">Aminopterin</span> Chemical compound

Aminopterin, the 4–amino derivative of folic acid, is an antineoplastic drug with immunosuppressive properties often used in chemotherapy. Aminopterin is a synthetic derivative of pterin. Aminopterin works as an enzyme inhibitor by competing for the folate binding site of the enzyme dihydrofolate reductase. Its binding affinity for dihydrofolate reductase effectively blocks tetrahydrofolate synthesis. This results in the depletion of nucleotide precursors and inhibition of DNA, RNA, and protein synthesis.

<span class="mw-page-title-main">Coumatetralyl</span> Chemical compound

Coumatetralyl is an anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type used as a rodenticide.

<span class="mw-page-title-main">Toxicity class</span> Pesticide classification system

Toxicity class refers to a classification system for pesticides that has been created by a national or international government-related or -sponsored organization. It addresses the acute toxicity of agents such as soil fumigants, fungicides, herbicides, insecticides, miticides, molluscicides, nematicides, or rodenticides.

<span class="mw-page-title-main">4-Hydroxycoumarins</span> Group of anticoagulant drugs

4-Hydroxycoumarins are a class of vitamin K antagonist (VKA) anticoagulant drug molecules. Chemically, they are derived from coumarin by adding a hydroxy group at the 4 position to obtain 4-hydroxycoumarin, then adding a large aromatic substituent at the 3-position. The large 3-position substituent is required for anticoagulant activity.

<span class="mw-page-title-main">Brodifacoum</span> Chemical compound

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.

<span class="mw-page-title-main">Diphenadione</span> Chemical compound

Diphenadione is a vitamin K antagonist that has anticoagulant effects and is used as a rodenticide against rats, mice, voles, ground squirrels and other rodents. The chemical compound is an anti-coagulant with active half-life longer than warfarin and other synthetic 1,3-indandione anticoagulants.

<span class="mw-page-title-main">Methiocarb</span> Chemical compound

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

<span class="mw-page-title-main">Difenacoum</span> Chemical compound

Difenacoum is an anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type. It has anticoagulant effects and is used commercially as a rodenticide. It was first introduced in 1976 and first registered in the USA in 2007.

<span class="mw-page-title-main">Vitamin K antagonist</span> Group of substances

Vitamin K antagonists (VKA) are a group of substances that reduce blood clotting by reducing the action of vitamin K. The term "vitamin K antagonist" is technically a misnomer, as the drugs do not directly antagonize the action of vitamin K in the pharmacological sense, but rather the recycling of vitamin K. Vitamin K antagonists (VKAs) have been the mainstay of anticoagulation therapy for more than 50 years.

<span class="mw-page-title-main">Flocoumafen</span> Chemical compound

Flocoumafen is a fluorinated, second-generation anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type. It is a second generation chemical in this class, used commercially as a rodenticide. It has a very high toxicity and is restricted to indoor use and sewers. This restriction is mainly due to the increased risk to non-target species, especially due to its tendency to bio-accumulate in exposed organisms. Studies have shown that rodents resistant to first-generation anticoagulants can be adequately controlled with flocoumafen. It was synthesized in 1984 by Shell International Chemical.

<span class="mw-page-title-main">Chlorophacinone</span> Chemical compound

Chlorophacinone is a first-generation anticoagulant rodenticide. The mechanism of action results in internal bleeding due to non-functional clotting factors. It was used as a toxin to control rodent populations. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

<span class="mw-page-title-main">Crimidine</span> Chemical compound

Crimidine is a convulsant poison used as a rodenticide. Crimidine was originally known by its product name, Castrix. It was originally produced in the 1940s by the conglomerate, IG Farben. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. It is also no longer used in the United States as a rodenticide, but is still used to this day in other countries.

<span class="mw-page-title-main">Norbormide</span> Chemical compound

Norbormide is a toxic compound used as a rodenticide. It has several mechanisms of action, acting as a vasoconstrictor and calcium channel blocker, but is selectively toxic to rats and has relatively low toxicity to other species, due to a species specific action of opening the permeability transition pores in rat mitochondria.

α-Naphthylthiourea Chemical compound

α-Naphthylthiourea (ANTU) is an organosulfur compound with the formula C10H7NHC(S)NH2. This a white, crystalline powder although commercial samples may be off-white. It is used as a rodenticide and as such is fairly toxic. Naphthylthiourea is available as 10% active baits in suitable protein- or carbohydrate-rich materials and as a 20% tracking powder.

<span class="mw-page-title-main">Triazofos</span> Chemical compound

Triazofos is a chemical compound used in acaricides, insecticides, and nematicides.

<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an organic compound with the chemical formula FCH2CO2CH3. It is the extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

References

  1. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
  2. 1 2 3 Bromadiolone Archived December 21, 2006, at the Wayback Machine
  3. 1 2 "The Veterinarian's Guide to accidental rodenticide ingestion by dogs & cats" (PDF). Archived from the original (PDF) on 2016-07-09. Retrieved 2016-08-03.
  4. "Bromadiolone (Bromone, Maki) Chemical Profile 1/85". Pesticide Management Education Program, Cornell University. Archived from the original on 2019-09-04. Retrieved 2021-05-24.