Deltamethrin
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Deltamethrin is a
pyrethroid A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. I ...
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...
insecticide. Deltamethrin plays a key role in controlling
malaria Malaria is a mosquito-borne infectious disease that affects humans and other animals. Malaria causes symptoms that typically include fever, tiredness, vomiting, and headaches. In severe cases, it can cause jaundice, seizures, coma, or death. S ...
vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets; however, resistance of mosquitos and bed bugs to deltamethrin has seen a widespread increase. Deltamethrin is toxic to aquatic life, particularly fish. Although generally considered safe to use around humans, it is still
neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specificall ...
. It is an
allergen An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical terms ...
and causes
asthma Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, co ...
in some people.


Usage

Deltamethrin is a highly effective insecticide. It is used, among other applications, for the production of long-lasting insecticidal nets (LLINs), which, along with indoor residual spraying (IRS), are the main vector control strategies recommended by the World Health Organization (WHO) for the management of malaria. Deltamethrin plays a key role in controlling
malaria Malaria is a mosquito-borne infectious disease that affects humans and other animals. Malaria causes symptoms that typically include fever, tiredness, vomiting, and headaches. In severe cases, it can cause jaundice, seizures, coma, or death. S ...
vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets. It is used as one of a battery of pyrethroid insecticides in control of malarial vectors, particularly '' Anopheles gambiae'', and whilst being the most employed pyrethroid insecticide, can be used in conjunction with, or as an alternative to,
permethrin Permethrin is a medication and an 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 onto clothing or mosquito nets to kill the insects th ...
, cypermethrin and organophosphate-based insecticides, such as malathion and fenthion. Resistance to deltamethrin (and its counterparts) is now extremely widespread and threatens the success of worldwide vector control programmes.


Production

Deltamethrin is a pyrethroid composed of a single stereoisomer, of a possible 8 stereoisomers, selectively prepared by the esterification of (1''R'',3''R'')- or ''cis''-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylic acid with (''alpha'',''S'')- or (+)-''alpha''-cyano-3-phenoxybenzyl alcohol or by selective recrystallization of the racemic esters obtained by esterification of the (1''R'',3''R'')- or ''cis''-acid with the racemic or (''alpha''-''R'', ''alpha''-''S'', or ''alpha''-''R''/''S'')- or + or − alcohol.


Resistance

Resistance has been identified in several insects, including important vectors of malaria like the mosquito ''Anopheles gambiae'' as well as non-disease carrying pests like bed bugs.


Mosquitoes

Methods of resistance include thickening of the cuticle of the insect to limit permeation of the insecticide, metabolic resistance via overexpression of metabolizing
cytochrome P450 Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various co ...
mono-oxygenases and glutathione-S-transferases, and the
knockdown resistance Knockdown resistance, also called kdr, describes cases of resistance to diphenylethane (e.g. DDT) and pyrethroid insecticides in insects and other arthropods that result from reduced sensitivity of the nervous system caused by point mutations in ...
(kdr) sodium channel mutations which render the action of insecticides ineffectual, even when co-administered with piperonyl butoxide. Characterization of the different forms of resistance among mosquitoes has become a top priority in groups studying tropical medicine due to the high mortality of those who reside in endemic areas.


Bed bugs

Two mutations, the valine to leucine mutation (V419L) and the leucine to isoleucine mutation (L925I) in voltage-gated sodium channel α-subunit gene, have been identified as responsible for knockdown resistance to deltamethrin in bed bugs. One study found that 88% of bed bug populations in the US had at least one of the two mutations, if not both, meaning that deltamethrin resistance among bed bugs is currently making this insecticide obsolete.


Side effects

Deltamethrin belongs to a group of pesticides called synthetic pyrethroids. This pesticide is toxic to aquatic life, particularly fish, and therefore must be used with extreme caution around water.


In humans

Although generally considered safe to use around humans, it is still
neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specificall ...
. Pyrethroids like Deltamethrin can be
allergen An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical terms ...
s and cause
asthma Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, co ...
in some people. Deltamethrin temporarily attacks the nervous system of any animal with which it comes into contact. Skin contact can lead to tingling or reddening of the skin local to the application. If taken in through the eyes or mouth, the most common symptom is facial
paraesthesia Paresthesia is an abnormal sensation of the skin (tingling, pricking, chilling, burning, numbness) with no apparent physical cause. Paresthesia may be transient or chronic, and may have any of dozens of possible underlying causes. Paresthesias ar ...
, which can feel like many different abnormal sensations, including burning, partial numbness, "pins and needles", skin crawling, etc. There is one case report describing chronic intoxication from pyrethroid insecticides leading to a syndrome clinically similar to motor neuron disease. There are no
antidote An antidote is a substance that can counteract a form of poisoning. The term ultimately derives from the Greek term φάρμακον ἀντίδοτον ''(pharmakon) antidoton'', "(medicine) given as a remedy". Antidotes for anticoagulants are s ...
s, and treatment must be symptomatic, as approved by a physician. Over time, deltamethrin is metabolized, with a rapid loss of toxicity, and passed from the body. A poison control center should be contacted in the event of an accidental poisoning. Deltamethrin is able to pass from a woman's skin through her blood and into her breast milk, although breastfeeding remains safe under prevailing conditions. In South Africa, residues of deltamethrin were found in breast milk, together with
DDT Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound, an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. ...
, in an area that used DDT treatment for malaria control, as well as pyrethroids in
small-scale agriculture A smallholding or smallholder is a small farm operating under a small-scale agriculture model. Definitions vary widely for what constitutes a smallholder or small-scale farm, including factors such as size, food production technique or technology ...
. A 2015 study conducted in
Brittany Brittany (; french: link=no, Bretagne ; br, Breizh, or ; Gallo: ''Bertaèyn'' ) is a peninsula, historical country and cultural area in the west of modern France, covering the western part of what was known as Armorica during the period ...
, France, found a negative correlation between deltamethrin exposure (measured through the presence of a metabolite in urine) and cognitive scores in infants.


In domestic animals

Cases of toxicity have been observed in cattle, following use of agricultural deltamethrin preparation in external application for
tick Ticks (order Ixodida) are parasitic arachnids that are part of the mite superorder Parasitiformes. Adult ticks are approximately 3 to 5 mm in length depending on age, sex, species, and "fullness". Ticks are external parasites, living by ...
control. It is also commonly known as having severe poisoning effects on the cattle, which are vulnerable to the pyrethroid.


References


External links


Deltamethrin General Fact Sheet - National Pesticide Information CenterDeltamethrin Technical Fact Sheet - National Pesticide Information Center
- IPCS INCHEM
Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
* ttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4415012/ Deltamethrin Development Exposure - FASEB Journal {{Insecticides Organobromides (cyano-(3-phenoxyphenyl)methyl) 2,2,3-trimethylcyclopropane-1-carboxylates Pyrethroids