Diphenadione

Last updated
Diphenadione
Diphenadione2.svg
Diphenadione 3D ball.png
Names
Preferred IUPAC name
2-(Diphenylacetyl)-1H-indene-1,3(2H)-dione
Other names
Diphacinone; Diphenandione, Difenacin, [1] Ratindan [2] [3]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.304 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H
    Key: JYGLAHSAISAEAL-UHFFFAOYSA-N
  • InChI=1/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H
    Key: JYGLAHSAISAEAL-UHFFFAOYAR
  • O=C2c1ccccc1C(=O)C2C(=O)C(c3ccccc3)c4ccccc4
Properties
C23H16O3
Molar mass 340.378 g·mol−1
Pharmacology
B01AA10 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. [3] [4]

It is toxic to mammals, in all forms; exposure and oral ingestion of the toxin may cause irregular heartbeat and major maladies associated with its impact on blood clotting, depending on dose. [5] As a "second-generation" anticoagulant, diphenadione is more toxic than the first generation compounds (e.g., warfarin). [6] :436 For purposes of treating toxicity on exposure, diphenadione is grouped with other vitamin K antagonists (coumarins and indandiones); despite being directed at rodents and being judged as less hazardous to humans and domestic animals than other rodenticides in use[ when? ] (by the U.S. Environmental Protection Agency), indandione anticoagulants, nevertheless, "may cause human toxicity at a much lower dose than conventional 'first-generation anticoagulants'… and can bioaccumulate in the liver." [7] :173

Related Research Articles

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

Warfarin Medication used as an anticoagulant

Warfarin, sold under the brand name Coumadin among others, is a medication that is used as an anticoagulant. It is commonly used to treat blood clots such as deep vein thrombosis and pulmonary embolism, and to prevent 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 generally taken by mouth, but may also be used by injection into a vein.

Rodenticide 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, squirrels, woodchucks, chipmunks, porcupines, nutria, beavers, and voles.

Coumarin Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C
9
H
6
O
2
. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone.

Persistent organic pollutant Organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes

Persistent organic pollutants (POPs), sometimes known as "forever chemicals" are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. It is a toxic chemical that adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released. The effect of POPs on human and environmental health was discussed, with intention to eliminate or severely restrict their production, by the international community at the Stockholm Convention on Persistent Organic Pollutants in 2001. The United States has taken strong domestic action to reduce emissions of POPs. For example, none of the original POPs pesticides listed in the Stockholm Convention is registered for sale and distribution in the United States today and in 1978, Congress prohibited the manufacture of PCBs and severely restricted the use of remaining PCB stocks. In addition, since 1987, EPA and the states have effectively reduced environmental releases of dioxins and furans to land, air, and water from U.S. sources.

Bromethalin Chemical compound

Bromethalin is a neurotoxic rodenticide that damages the central nervous system.

Calcium phosphide Chemical compound

Calcium phosphide (CP) is the inorganic compound with the formula Ca3P2. It is one of several phosphides of calcium, being described as the salt-like material composed of Ca2+ and P3−. Other, more exotic calcium phosphides have the formula CaP, CaP3, Ca2P2, and Ca5P8.

Coumatetralyl Chemical compound

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

Zinc phosphide Chemical compound

Zinc phosphide (Zn3P2) is an inorganic chemical compound. It is a grey solid, although commercial samples are often dark or even black. It is used as a rodenticide. Zn3P2 is a II-V semiconductor with a direct band gap of 1.5 eV and may have applications in photovoltaic cells. A second compound exists in the zinc-phosphorus system, zinc diphosphide (ZnP2).

Tetramethylenedisulfotetramine Chemical compound

Tetramethylenedisulfotetramine (TETS) is an organic compound that is used as a rodenticide. It is an odorless, tasteless white powder that is slightly soluble in water, DMSO and acetone, and insoluble in methanol and ethanol. TETS is a sulfamide derivative. It can be synthesized by reacting sulfamide with formaldehyde under acidic condition. When crystallized from acetone, it forms cubic crystals with a melting point of 255–260 °C.

Dicoumarol

Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.

4-Hydroxycoumarins

4-Hydroxycoumarins belong to a class of vitamin K antagonist (VKA) anticoagulant drug molecules 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.

Brodifacoum 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 possum.

Bromadiolone Chemical compound

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.

Vitamin K antagonist

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 antagonise the action of vitamin K in the pharmacological sense, but rather the recycling of vitamin K.

Chlorophacinone Chemical compound

Chlorophacinone is an anticoagulant used as a rodenticide. 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.

Crimidine 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.

Carbophenothion Chemical compound

Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.

d-CON American brand of rodent control products

d-CON is an American brand of rodent control products owned and distributed in the United States by the UK-based consumer goods company Reckitt. The d-CON product line includes traps and baits for use around the home for trapping and killing rats and mice. As of 2015, bait products use first-generation vitamin K anticoagulants as poison.

1-(4-Chlorophenyl)silatrane is an extremely toxic organosilicon compound which was developed by M&T Chemicals as a single-dose rodenticide. It was never registered as rodenticide, except for experimental use. 1-(4-Chlorophenyl)silatrane was one of the chemicals studied in the Project Coast.

References

  1. Kukovinets, O. S.; Abdullin, M. I.; Zainullin, R. A.; Kunakova, R. V. (2008). Chemical and Physical Methods for Protecting Biopolymers Against Pests. New York: Nova Biomedical Books. p. 185. ISBN   9781604563313.
  2. "Catalog.md" . Retrieved 3 April 2020.
  3. 1 2 EXTOXNET Staff (1993-09-01). "Diphacinone". EXTOXNET. Retrieved 2011-12-07.
  4. Meister, R.T. (ed.). 1992. Farm Chemicals Handbook '92. Meister Publishing Company, Willoughby, OH.
  5. Bell Laboratories, Inc. July, 1990. Diphacinone Technical: MSDS. Bell Labs, Madison, WI.
  6. Murphy, Michael J.; Talcott, Patricia A. (2013). "Anticoagulant Rodenticides (Ch. 32)". In Peterson, Michael E.; Talcott, Patricia A. (eds.). Small Animal Toxicology (3rd ed.). St. Louis, MO, US: Elsevier Health Sciences. pp. 435–446, esp. 435–439. ISBN   978-0323241984 . Retrieved 5 April 2016.
  7. Reigart, J. Routt & Roberts, James R. (Eds.) (2013). "Rodenticides (Ch. 18, § Coumarins and Indandiones)" (PDF). Recognition and Management of Pesticide Poisonings (6th ed.). Corvallis, OR, US: National Pesticide Information Center (Oregon State University and the U.S. Environmental Protection Agency . Retrieved 5 April 2016. The first-generation anticoagulants, for example, are reasonably effective against pest rodents and are less toxic than second-generation anticoagulants… / Very small amounts of the extremely toxic rodenticides sodium fluoroacetate, fluoracetamide, strychnine, crimidine, yellow phosphorus, zinc phosphide and thallium sulfate can cause severe and even fatal poisoning. Cholecalciferol is also a highly toxic agent. The anticoagulants, indandiones and red squill, are less hazardous to humans and domestic animals. Some of the newer anticoagulant compounds, termed 'second-generation anticoagulants,' may cause human toxicity at a much lower dose than conventional 'first-generation anticoagulants'… and can bioaccumulate in the liver…CS1 maint: multiple names: authors list (link) CS1 maint: extra text: authors list (link) [p. 173, emphasis in source].

Further reading