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 ''Chrysanthemum coccineum, C. coccineum''). Pyrethroids are used as commercial and hou ...
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
. Deltamethrin plays a key role in controlling
malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...
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. It is an
allergen An allergen is an otherwise harmless substance that triggers an allergic reaction in sensitive individuals by stimulating an immune response. In technical terms, an allergen is an antigen that is capable of stimulating a type-I hypersensitivi ...
and causes
asthma Asthma is a common 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 wh ...
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 disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...
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, cypermethrin and
organophosphate In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...
-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 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...
mono-oxygenases and glutathione-S-transferases, and the knockdown resistance (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 bug Bed bugs are parasitic insects from the genus ''Cimex'', which are micropredators that haematophagy, feed on blood, usually at night. Their bites can result in a number of health impacts, including skin rashes, psychological effects, and aller ...
s. 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, it is neurotoxic to humans in high doses. Pyrethroids like Deltamethrin can also be an
allergen An allergen is an otherwise harmless substance that triggers an allergic reaction in sensitive individuals by stimulating an immune response. In technical terms, an allergen is an antigen that is capable of stimulating a type-I hypersensitivi ...
that provokes
asthma Asthma is a common 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 wh ...
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, 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 antidotes, 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 Breast milk (sometimes spelled as breastmilk) or mother's milk is milk produced by the mammary glands in the breasts of women. Breast milk is the primary source of nutrition for newborn infants, comprising fats, proteins, carbohydrates, and a var ...
, together with DDT, in an area that used DDT treatment for malaria control, as well as pyrethroids in small-scale agriculture. A 2015 study conducted in
Brittany Brittany ( ) is a peninsula, historical country and cultural area in the north-west of modern France, covering the western part of what was known as Armorica in Roman Gaul. It became an Kingdom of Brittany, independent kingdom and then a Duch ...
, 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 control.


References


External links


Deltamethrin Technical Fact Sheet - National Pesticide Information CenterDeltamethrin General Fact sheet - National Pesticide Information Center

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