Difethialone

Last updated
Difethialone
Difethialone.png
Names
Preferred IUPAC name
3-[3-(4′-Bromo[1,1′-biphenyl]-4-yl)naphthalen-1-yl]-4-hydroxy-2H-1-benzothiopyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.118.383 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C31H23BrO2S/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2 X mark.svgN
    Key: JHELOZJAKXYVBE-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C31H23BrO2S/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2
    Key: JHELOZJAKXYVBE-UHFFFAOYAX
  • O=c1c(C2CC(c3ccc(-c4ccc(Br)cc4)cc3)Cc3ccccc32)c(O)sc2ccccc12
Properties
C31H23BrO2S
Molar mass 539.49 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Difethialone is an anticoagulant used as a rodenticide. [1] It is considered a second generation agent. [2]

In May 2008, the EPA added restrictions on the sale of difethialone in consumer-use rodenticide products and also for exterior use by commercial applicators. [3] [4]

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.

<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">Coumarin</span> Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and considered as a lactone.

<span class="mw-page-title-main">Toxic Substances Control Act of 1976</span> United States federal law

The Toxic Substances Control Act (TSCA) is a United States law, passed by the 94th United States Congress in 1976 and administered by the United States Environmental Protection Agency (EPA), that regulates chemicals not regulated by other U.S. federal statutes, including chemicals already in commerce and the introduction of new chemicals. When the TSCA was put into place, all existing chemicals were considered to be safe for use and subsequently grandfathered in. Its three main objectives are to assess and regulate new commercial chemicals before they enter the market, to regulate chemicals already existing in 1976 that posed an "unreasonable risk of injury to health or the environment", as for example PCBs, lead, mercury and radon, and to regulate these chemicals' distribution and use.

<span class="mw-page-title-main">Federal Insecticide, Fungicide, and Rodenticide Act</span> US federal law governing pesticide regulation

The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) is a United States federal law that set up the basic U.S. system of pesticide regulation to protect applicators, consumers, and the environment. It is administered and regulated by the United States Environmental Protection Agency (EPA) and the appropriate environmental agencies of the respective states. FIFRA has undergone several important amendments since its inception. A significant revision in 1972 by the Federal Environmental Pesticide Control Act (FEPCA) and several others have expanded EPA's present authority to oversee the sales and use of pesticides with emphasis on the preservation of human health and protection of the environment by "(1) strengthening the registration process by shifting the burden of proof to the chemical manufacturer, (2) enforcing compliance against banned and unregistered products, and (3) promulgating the regulatory framework missing from the original law".

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

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

<span class="mw-page-title-main">4-Hydroxycoumarins</span>

4-Hydroxycoumarins are 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.

<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">Tioclomarol</span> Chemical compound

Tioclomarol is an anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type. It is a second generation drug, used as a rodenticide that is effective for the control of rodents that are resistant to this class of drugs.

<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">Food Quality Protection Act</span> US law about pesticides

The Food Quality Protection Act (FQPA), or H.R.1627, was passed unanimously by Congress in 1996 and was signed into law by President Bill Clinton on August 3, 1996. The FQPA standardized the way the Environmental Protection Agency (EPA) would manage the use of pesticides and amended the Federal Insecticide, Fungicide, and Rodenticide Act and the Federal Food Drug and Cosmetic Act. It mandated a health-based standard for pesticides used in foods, provided special protections for babies and infants, streamlined the approval of safe pesticides, established incentives for the creation of safer pesticides, and required that pesticide registrations remain current.

<span class="mw-page-title-main">Bromadiolone</span> 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.

<span class="mw-page-title-main">Household hazardous waste</span>

Household hazardous waste (HHW) was a term coined by Dave Galvin from Seattle, Washington in 1982 as part of the fulfillment of a US EPA grant. This new term was reflective of the recent passage of the Resource Conservation and Recovery Act of 1976 in the US. This act and subsequent regulations strengthened the environmental protection requirements for landfills, in Subpart D, and created a "cradle to grave" management system for hazardous wastes, in Subpart C. From RCRA 1976 the US EPA promulgated rules in 1980 which explicitly excluded any wastes from household origins from regulation as a hazardous waste at the federal level. Most US states adopted parallel regulations to RCRA 1976 but were allowed to be more stringent. California took advantage of this allowance and chose to not exempt household origin wastes from their state hazardous waste laws. HHW products exhibit many of the same dangerous characteristics as fully regulated hazardous waste which are their potential for reactivity, ignitability, corrosivity, toxicity, or persistence. Examples include drain cleaners, oil paint, motor oil, antifreeze, fuel, poisons, pesticides, herbicides and rodenticides, fluorescent lamps, lamp ballasts containing PCBs, some smoke detectors, and in some states, consumer electronics. Except for California, most states exclude HHW from their hazardous waste regulations and regulate the management of HHW largely under their solid waste regulatory schemes.

<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>

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">California Department of Pesticide Regulation</span>

The California Department of Pesticide Regulation, also known as DPR or CDPR, is one of six boards and departments of the California Environmental Protection Agency (Cal/EPA).

<span class="mw-page-title-main">4-Hydroxycoumarin</span> Chemical compound

4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.

d-CON American brand of rodent control products

d-CON is a brand of rodent control products, which is distributed and owned in the United States by the UK-based consumer goods company Reckitt.

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. Nahas K, Lorgue G, Mazallon M (1989). "Difethialone (LM-2219): a new anticoagulant rodenticide for use against warfarin-resistant and -susceptible strains of Rattus norvegicus and Mus musculus". Annales de Recherches Vétérinaires. 20 (2): 159–64. PMID   2751229.
  2. Saravanan K, Kanakasabai R, Thiyagesan K (June 2003). "Field evaluation of difethialone, a new second generation anticoagulant rodenticide in the rice fields". Indian Journal of Experimental Biology. 41 (6): 655–8. PMID   15266918.
  3. EPA, OCSPP, OPP, US (2014-03-04). "Restrictions on Rodenticide Products". www.epa.gov.
  4. "Regulations.gov". www.regulations.gov.