Cyfluthrin

Last updated
Cyfluthrin
Cyfluthrin Marco 201809017.svg
Cyfluthrin 3D.png
Names
Preferred IUPAC name
(R)-Cyano(4-fluoro-3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.063.485 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1 Yes check.svgY
    Key: QQODLKZGRKWIFG-QSFXBCCZSA-N Yes check.svgY
  • InChI=1/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1
    Key: QQODLKZGRKWIFG-QSFXBCCZBF
  • Cl/C(Cl)=C/[C@H]3[C@@H](C(=O)O[C@@H](C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C
Properties
C22H18Cl2FNO3
Molar mass 434.29 g·mol−1
Melting point 60 °C (140 °F; 333 K)
2 μg/L
Pharmacology
P03BA01 ( WHO ) QP53AC12 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Cyfluthrin is a pyrethroid insecticide and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of isomers. Like most pyrethroids (MoA 3a), [1] it is highly toxic to fish and invertebrates, but it is far less toxic to humans. [2] It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.

Contents

Safety

In rats, the LD50s are 500, 800 (oral), and 600 (skin) mg/kg. [2]

Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures. In humans, it is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, whose urinary excretion half-lives are in a range of 5–7 hours. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantification of cyfluthrin in blood or plasma. [3]

Health and safety risks are controlled by right to know laws that exist in most developed countries. Cyfluthrin is regulated in the US by the EPA. [4]

See also

Related Research Articles

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Cypermethrin Chemical compound

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Piperonyl butoxide Chemical compound

Piperonyl butoxide (PBO) is a waxy white solid organic compound used as a synergist component of pesticide formulations. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole.

Pyrethrin

The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.

Bifenthrin Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations, including the invasive red fire ant, by influencing its nervous system. It has a high toxicity to aquatic organisms.

Pyrethroid

A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.

Permethrin Medication and insecticide

Permethrin, sold under the brand name Nix among others, is a medication and insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed on clothing or mosquito nets to kill the insects that touch them.

Chlorfenvinphos Chemical compound

Chlorfenvinphos is the common name of 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 cancelled in 1991.

Organophosphate

Organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid. Like most functional groups organophosphates occur in a diverse range of forms, with important examples including key biomolecules such as DNA, RNA and ATP, as well as many insecticides, herbicides, nerve agents and flame retardants. OPEs have been widely used in various products as flame retardants, plasticizers, and performance additives to engine oil. The popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants. The low cost of production and compatibility to different polymers made OPEs to be widely used in different industries including textile, furniture, electronics as plasticizers and flame retardants. These compounds are added to the final product physically rather than by chemical bond. Due to this OPEs leak into the environment more readily through volatilization, leaching, as well as abrasion. OPEs have been detected in different environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.

Diazinon Chemical compound

Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.

Allethrins

The allethrins are a group of related synthetic compounds used in insecticides. They are synthetic pyrethroids, a synthetic form of a chemical found naturally in the chrysanthemum flower. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.

Deltamethrin Chemical compound

Deltamethrin is a pyrethroid ester insecticide. Deltamethrin plays a key role in controlling malaria vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets; however, resistance of mosquitos and bed bugs to deltamethrin is becoming widespread.

Dichlorvos

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961 and has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. The insecticide has been banned in EU since 1998.

Nitenpyram Insecticide

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Cyhalothrin Synthetic pyrethroid used as insecticide

Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

Etofenprox Chemical compound

Etofenprox is a pyrethroid derivative which is used as an insecticide. Mitsui Chemicals Agro Inc. is the main manufacturer of the chemical. It is also used as an ingredient in flea medication for cats and dogs.

Acetamiprid Chemical compound

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

Tefluthrin Synthetic pyrethroid used as insecticide

Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.

References

  1. "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
  2. 1 2 Robert L. Metcalf (2002). "Insect Control". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_263.
  3. R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 388–389.
  4. "Pyrethroids and Pyrethrins". United States Environmental Protection Agency.