Deltamethrin

Deltamethrin
IUPAC name [(S)-cyano-(3-phenoxyphenyl)-methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-1-carboxylate
Other names Deltamethrin Decamethrin
Identifiers
CAS number	52918-63-5 Y
ChemSpider	37079 Y
UNII	2JTS8R821G Y
KEGG	D07785 Y
ChEBI	CHEBI:4388 Y
ChEMBL	CHEMBL1593566 N
ATCvet code	QP53AC11
Jmol-3D images	Image 1
SMILES Br/C(Br)=C/[C@H]3[C@@H](C(=O)O[C@H](C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
InChI 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 Y Key: OWZREIFADZCYQD-NSHGMRRFSA-N Y 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
Properties
Molecular formula	C22H19Br2NO3
Molar mass	505.21 g mol−1
Density	1.5 g cm−3
Melting point	98 °C, 371 K, 208 °F
Boiling point	300 °C, 573 K, 572 °F
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Deltamethrin is a pyrethroid ester insecticide.

Usage

Deltamethrin products are among the most popular and widely used insecticides in the world^{[citation needed]} and have become very popular with pest control operators and individuals in the United States in the past five years.^[1] This material is a member of one of the safest classes of pesticides: synthetic pyrethroids. While mammalian exposure to deltamethrin is classified as safe^{[citation needed]}, this pesticide is highly toxic to aquatic life, particularly fish, and therefore must be used with extreme caution around water. It is neurotoxic to humans and has been found in human breast milk.^[2]

There are many uses for deltamethrin, ranging from agricultural uses to home pest control. Deltamethrin has been instrumental in preventing the spread of diseases carried by tick-infested prairie dogs, rodents and other burrowing animals^{[citation needed]}. It is helpful in eliminating and preventing a wide variety of household pests, especially spiders, fleas, ticks, carpenter ants, carpenter bees, cockroaches and bedbugs. Deltamethrin is also one of the primary ingredients in ant chalk.

Malaria control

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 other 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.

Resistance to deltamethrin

Resistance has been characterised in several important vectors of malaria, including Anopheles gambiae. Methods of resistance include thickening of the cuticle of the vector to facilitate less permeation of the insecticide, metabolic resistance via overexpression of metabolising P450 mono-oxygenases and glutathione-S-transferases, and the kdr sodium channel mutations which render the action of insecticides ineffectual, even when co-administered with piperonyl butoxide. Characterisation of the different forms of resistance has become a top priority in groups studying tropical medicine due to the high mortality of those who reside in endemic areas (Muller, Pie, et al. (2008). Field caught Permethrin-Resistant Anopheles gambiae overexpress CYP6P3, a P450 that metabolises pyrethroids,PLoS Genetics 4(11)).

Poisoning

In humans

While deltamethrin is easy to use and very effective, it should always be treated with caution. It should be applied according to the instructions that come with the insecticide. When care is not taken, deltamethrin poisoning can occur.

Since deltamethrin is a neurotoxin, it attacks the nervous system. Skin contact can lead to tingling or reddening of the skin local to the application. If taken in through the eyes or mouth, a common symptom is facial paraesthesia, which can feel like many different abnormal sensations, including burning, partial numbness, "pins and needles", skin crawling, etc. There are no reports indicating that chronic intoxication from pyrethroid insecticides causes motor neuron damage or motor neuron disease.^[3] However, in 2011, a case report was published demonstrating pathologically proven motor neuron death in a Japanese woman after acute massive ingestion of pesticides containing pyrethroids and organochlorine. ^[4]

Recently, in South Africa, residues of deltamethrin were found in breast milk, together with DDT, in an area that used DDT treatment for malaria control, as well as pyrethroids in small-scale agriculture.^[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.

In domestic animals

Cases of toxicity have been observed in cattle, following use of agricultural deltamethrin preparation in external application in tick control. Symptoms appeared 36 hours after the application, and included muscular tremors that lead to decubitus 12 hours later. After 12 hours, there was spontaneous recovery and the animal could stand up again, although the muscular tremors persisted. The body temperature was then 38.3°C. (normal range 38.0 to 39.5°C.).^{[citation needed]}

References

1. ^ "Deltamethrin Odorless Synthetic Pyrethroid Insecticides". PestProducts.com. http://www.pestproducts.com/deltamethrin.htm. Retrieved 2008-09-26. 
2. ^ Bouwman, B. Sereda and H.M. Meinhardt, H.; B. Sereda and H.M. Meinhardt (December 2006). "Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa". Environmental Pollution 144 (3): 902–917. doi:10.1016/j.envpol.2006.02.002. PMID 16564119. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VB5-4JJGC5N-8&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_version=1&_urlVersion=0&_userid=10&md5=da8b08cb632d6d6a88bce3c6c8001bd3. Retrieved 2008-09-26. 
3. ^ Doi, et al (2006). "Motor neuron disorder simulating ALS induced by chronic inhalation of pyrethroid insecticides". Neurology 67 (10): pp. 1894–1895. doi:10.1212/01.wnl.0000244489.65670.9f. 
4. ^ Doi, et al (2006). "Motor neuron disorder simulating ALS induced by chronic inhalation of pyrethroid insecticides". Neurology 67 (10): pp. 1894–1895. doi:10.1212/01.wnl.0000244489.65670.9f. 
5. ^ Bouwman, B. Sereda and H.M. Meinhardt, H.; B. Sereda and H.M. Meinhardt (December 2006). "Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa". Environmental Pollution 144 (3): 902–917. doi:10.1016/j.envpol.2006.02.002. PMID 16564119. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VB5-4JJGC5N-8&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_version=1&_urlVersion=0&_userid=10&md5=da8b08cb632d6d6a88bce3c6c8001bd3. Retrieved 2008-09-26. 

External links

• Deltamethrin General Fact Sheet - National Pesticide Information Center
• Deltamethrin Technical Fact Sheet - National Pesticide Information Center
• Data Sheet on Pesticides No. 50 - IPCS INCHEM
• Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
• Deltamethrin Pesticide Information Profile - Extension Toxicology Network