Deltamethrin

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Deltamethrin
Deltamethrin
Deltamethrin
Names
Preferred IUPAC name
(S)-Cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
Other names
  • Decamethrin
  • Decis
  • Delta dust
  • DeltaGard
Identifiers
3D model (
JSmol
)
6746312
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.052.943 Edit this at Wikidata
EC Number
  • 258-256-6
KEGG
RTECS number
  • GZ1233000
UNII
UN number 3349
  • InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1 checkY
    Key: OWZREIFADZCYQD-NSHGMRRFSA-N checkY
  • InChI=1/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1
    Key: OWZREIFADZCYQD-NSHGMRRFBN
  • N#C[C@H](c1cccc(c1)Oc1ccccc1)OC(=O)[C@@H]1[C@@H](C1(C)C)C=C(Br)Br
Properties
C22H19Br2NO3
Molar mass 505.206 g·mol−1
Density 1.5 g cm−3
Melting point 98 °C (208 °F; 371 K)
Boiling point 300 °C (572 °F; 573 K)
Pharmacology
QP53AC11 (WHO
)
Hazards
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H331, H410
P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 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 and causes asthma 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.[1]

Deltamethrin plays a key role in controlling malaria 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-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 (1R,3R)- 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 (1R,3R)- 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 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.[2]

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 is currently making this insecticide obsolete.[3]

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. Pyrethroids like Deltamethrin can be allergens and cause asthma in some people.[4]

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

motor neuron disease.[5] 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

small-scale agriculture.[6]

A 2015 study conducted in Brittany, France, found a negative correlation between deltamethrin exposure (measured through the presence of a metabolite in urine) and cognitive scores in infants.[7]

In domestic animals

Cases of toxicity have been observed in cattle, following use of agricultural deltamethrin preparation in external application for tick control.[citation needed]

References

  1. ISBN 978-92-4-156515-8
    .
  2. PMID 19043575
    .
  3. PMID 20301216
    .
  4. ^ "Cockroach Control". Archived from the original on August 12, 2017. Retrieved August 10, 2016.
  5. S2CID 29920559
    .
  6. PMID 16564119
    .
  7. PMID 26057254
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Deltamethrin&oldid=1189034466"