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Revision as of 13:42, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Latest revision as of 18:33, 22 December 2024 edit undoCitation bot (talk | contribs)Bots5,429,133 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:(cyano-(3-phenoxyphenyl)methyl) 2,2,3-trimethylcyclopropane-1-carboxylates | #UCB_Category 1/9 
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| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396325007 | verifiedrevid = 460775019
| Name = ''Deltamethrin'' | Name = Deltamethrin
| ImageFile = Decamethrin-2D-skeletal.png | ImageFile = Decamethrin-2D-skeletal.png
⚫ | ImageName = Deltamethrin
<!-- | ImageSize = 300px -->
| ImageName = Deltamethrin | ImageFile1 = Deltamethrin-from-xtal-3D-bs-17.png
| ImageFile1 = Deltamethrin-3D-balls-2.png | ImageName1 = Deltamethrin
| ImageFile2 = Deltamethrin-from-xtal-3D-sf.png
<!-- | ImageSize1 = 300px -->
⚫ | PIN = (''S'')-Cyano(3-phenoxyphenyl)methyl (1''R'',3''R'')-3-(2,2-dibromoethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
⚫ | ImageName1 = Deltamethrin
| OtherNames =
⚫ | IUPACName = (1''R'',3''R'')-3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-1-carboxylate
{{Unbulleted list
| OtherNames = Deltamethrin<br />Decamethrin
| Decamethrin
⚫ | Section1 = {{Chembox Identifiers
| Decis
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Delta dust
| DeltaGard
}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 37079 | ChemSpiderID = 37079
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2JTS8R821G | UNII = 2JTS8R821G
| PubChem = 40585
| Beilstein = 6746312
| EC_number = 258-256-6
| RTECS = GZ1233000
| UNNumber = 3349
| 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 | 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
| InChIKey = OWZREIFADZCYQD-NSHGMRRFBN | InChIKey = OWZREIFADZCYQD-NSHGMRRFBN
Line 25: Line 35:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 52918-63-5 | CASNo = 52918-63-5
| ATCvet = yes
⚫ | ATCCode_prefix = P53
⚫ | ATCCode_suffix = AC11
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1593566 --> | ChEMBL = 1593566
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07785 | KEGG = D07785
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4388 | ChEBI = 4388
| SMILES = Br/C(Br)=C/3(C(=O)O(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C | SMILES = N#C(c1cccc(c1)Oc1ccccc1)OC(=O)1(C1(C)C)C=C(Br)Br
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=22 | H=19 | Br=2 | N=1 | O=3
| Formula = C<sub>22</sub>H<sub>19</sub>Br<sub>2</sub>NO<sub>3</sub>
| MolarMass = 505.21 g mol<sup>−1</sup> | Density = 1.5 g cm<sup>−3</sup>
| MeltingPtC = 98
| Density = 1.5 g cm<sup>−3</sup>
| MeltingPtC = 98 | BoilingPtC = 300
| BoilingPtC = 300
}} }}
|Section6={{Chembox Pharmacology
⚫ | ATCCode_prefix = P03
⚫ | ATCCode_suffix = BA03
| ATC_Supplemental = {{ATCvet|P53|AC11}}
}} }}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS06}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|331|410}}
| PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+340|311|321|330|391|403+233|405|501}}
}}
}}

'''Deltamethrin''' is a ] ] ]. Deltamethrin plays a key role in controlling ] vectors, and is used in the manufacture of long-lasting insecticidal ]s; 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 ]. It is an ] and causes ] in some people.
'''Deltamethrin''' is a ] ] ].


==Usage== ==Usage==
Deltamethrin products are among the most popular and widely used insecticides in the world{{Citation needed|date=September 2008}} and have become very popular with pest control operators and individuals in the United States in the past five years.<ref>{{cite web|url=http://www.pestproducts.com/deltamethrin.htm|title=Deltamethrin Odorless Synthetic Pyrethroid Insecticides |publisher=PestProducts.com |accessdate=2008-09-26}}</ref> This material is a member of one of the safest classes of pesticides: synthetic ]s. While mammalian exposure to deltamethrin is classified as safe{{Citation needed|date=September 2011}}, 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.<ref>{{cite journal|last=Bouwman, B. Sereda and H.M. Meinhardt |first=H.|coauthors=B. Sereda and H.M. Meinhardt |date=December 2006|title=Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa |journal=Environmental Pollution|pmid=16564119|volume=144|issue=3|pages=902–917 |doi=10.1016/j.envpol.2006.02.002|url=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|accessdate=2008-09-26}}</ref>


Deltamethrin is a highly effective insecticide. It is used, among other applications, for the production of ] (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.<ref name=WMR2015>{{cite book|author=World Health Organization|title=World Malaria Report 2015|chapter-url=https://books.google.com/books?id=rg4LDgAAQBAJ&pg=PP1|date=30 January 2016|publisher=World Health Organization|isbn=978-92-4-156515-8|page=48 |chapter=5.5 Resistance to insecticides}}</ref>
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 ]s, ]s and other burrowing animals{{Citation needed|date=August 2009}}. It is helpful in eliminating and preventing a wide variety of household pests, especially ]s, ]s, ]s, ]s, ]s, ]es and ]s. Deltamethrin is also one of the primary ingredients in ].


⚫ Deltamethrin plays a key role in controlling ] vectors, and is used in the manufacture of long-lasting insecticidal ]s. It is used as one of a battery of pyrethroid insecticides in control of malarial vectors, particularly '']'', and whilst being the most employed pyrethroid insecticide, can be used in conjunction with, or as an alternative to, ], ] and ]-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.
==Malaria control==
⚫ Deltamethrin plays a key role in controlling ] vectors, and is used in the manufacture of long-lasting insecticidal ]s. 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.


==Production==
==Resistance to deltamethrin==
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 &minus; alcohol.
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 ]. Characterisation of the different forms of resistance has become a top priority in groups studying ] 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 == ==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.
⚫ === In humans ===


===Mosquitoes===
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.
Methods of resistance include thickening of the cuticle of the insect to limit permeation of the insecticide, metabolic resistance via overexpression of metabolizing ] mono-oxygenases and glutathione-S-transferases, and the ] (kdr) sodium channel mutations which render the action of insecticides ineffectual, even when co-administered with ]. Characterization of the different forms of resistance among mosquitoes has become a top priority in groups studying ] due to the high mortality of those who reside in endemic areas.<ref>{{cite journal | doi = 10.1371/journal.pgen.1000286| pmid = 19043575| title = Field-Caught Permethrin-Resistant Anopheles gambiae Overexpress CYP6P3, a P450 That Metabolises Pyrethroids| journal = PLOS Genetics| volume = 4| issue = 11| pages = e1000286| year = 2008| last1 = Müller| first1 = Pie| last2 = Warr| first2 = Emma| last3 = Stevenson| first3 = Bradley J.| last4 = Pignatelli| first4 = Patricia M.| last5 = Morgan| first5 = John C.| last6 = Steven| first6 = Andrew| last7 = Yawson| first7 = Alexander E.| last8 = Mitchell| first8 = Sara N.| last9 = Ranson| first9 = Hilary| last10 = Hemingway| first10 = Janet| last11 = Paine| first11 = Mark J. I.| last12 = Donnelly| first12 = Martin J.| pmc=2583951| doi-access = free}}</ref>


===Bed bugs===
Since deltamethrin is a ], 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 ], 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 ].<ref>{{cite article|author = Doi, ''et al''|title=Motor neuron disorder simulating ALS induced by chronic inhalation of pyrethroid insecticides|journal = Neurology|doi = 10.1212/01.wnl.0000244489.65670.9f |year= 2006 |volume = 67|number= 10|pages = 1894&ndash;1895 }}</ref> 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. <ref>{{cite article|author = Doi, ''et al''|title=Motor neuron disorder simulating ALS induced by chronic inhalation of pyrethroid insecticides|journal = Neurology|doi = 10.1212/01.wnl.0000244489.65670.9f |year= 2006 |volume = 67|number= 10|pages = 1894&ndash;1895 }}</ref>
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 ]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 ] is currently making this insecticide obsolete.<ref>{{Cite journal | last1 = Zhu | first1 = F. | last2 = Wigginton | first2 = J. | last3 = Romero | first3 = A. | last4 = Moore | first4 = A. | last5 = Ferguson | first5 = K. | last6 = Palli | first6 = R. | last7 = Potter | first7 = M. F. | last8 = Haynes | first8 = K. F. | last9 = Palli | first9 = S. R. | title = Widespread distribution of knockdown resistance mutations in the bed bug,Cimex lectularius(Hemiptera: Cimicidae), populations in the United States | doi = 10.1002/arch.20355 | journal = Archives of Insect Biochemistry and Physiology | volume = 73 | issue = 4 | pages = 245–57 | year = 2010 | pmid = 20301216| doi-access = free }}</ref>


== Side effects ==
⚫ Recently, in ], residues of deltamethrin were found in ], together with ], in an area that used ] treatment for ] control, as well as pyrethroids in small-scale agriculture.<ref>{{cite journal|last=Bouwman, B. Sereda and H.M. Meinhardt |first=H.|coauthors=B. Sereda and H.M. Meinhardt |date=December 2006|title=Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa |journal=Environmental Pollution|pmid=16564119|volume=144|issue=3|pages=902–917 |doi=10.1016/j.envpol.2006.02.002|url=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|accessdate=2008-09-26}}</ref>
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 ===
There are no ]s, and treatment must be symptomatic, as approved by a physician. Over time, deltamethrin is ], with a rapid loss of toxicity, and passed from the body. A ] should be contacted in the event of an accidental poisoning.
Although generally considered safe to use around humans, it is still ]. Pyrethroids like Deltamethrin can be ]s and cause ] in some people.<ref>{{cite web |url=https://www.pesticideresearch.com/site/?page_id=4843 |title=Cockroach Control |access-date=August 10, 2016 |archive-date=August 12, 2017 |archive-url=https://web.archive.org/web/20170812022459/http://www.pesticideresearch.com/site/?page_id=4843 |url-status=dead }}</ref>

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 ], 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 ].<ref name=Doi>{{cite journal | doi = 10.1212/01.wnl.0000244489.65670.9f| pmid = 17130437| title = Motor neuron disorder simulating ALS induced by chronic inhalation of pyrethroid insecticides| journal = Neurology| volume = 67| issue = 10| pages = 1894–5| year = 2006| last1 = Doi| first1 = H.| last2 = Kikuchi| first2 = H.| last3 = Murai| first3 = H.| last4 = Kawano| first4 = Y.| last5 = Shigeto| first5 = H.| last6 = Ohyagi| first6 = Y.| last7 = Kira| first7 = J.| s2cid = 29920559}}</ref> There are no ]s, and treatment must be symptomatic, as approved by a physician. Over time, deltamethrin is ], with a rapid loss of toxicity, and passed from the body. A ] 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 ], together with ], in an area that used DDT treatment for malaria control, as well as pyrethroids in ].<ref>{{cite journal|last1=Bouwman |first1=Sereda B. |first2=H.M. |last2=Meinhardt |date=December 2006|title=Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa |journal=Environmental Pollution |pmid=16564119|volume=144|issue=3|pages=902–917 |doi=10.1016/j.envpol.2006.02.002|bibcode=2006EPoll.144..902B }}</ref>

A 2015 study conducted in ], France, found a negative correlation between deltamethrin exposure (measured through the presence of a metabolite in urine) and cognitive scores in infants.<ref>{{cite journal|title=Pyrethroid insecticide exposure and cognitive developmental disabilities in children: The PELAGIE mother–child cohort|first1=Jean-François |last1=Viel |first2=Charline |last2=Warembourg |first3=Gaïd |last3=Le Maner-Idriss |first4=Agnès |last4=Lacroix |first5=Gwendolina |last5=Limond |first6=Florence |last6=Rouget |first7=Christine |last7=Monfort |first8=Gaël |last8=Durand |first9=Sylvaine |last9=Cordier |first10=Cécile |last10=Chevrier|journal=Environment International|volume=82|issue=September 2015|pages=69–75|doi=10.1016/j.envint.2015.05.009|pmid=26057254|year=2015|bibcode=2015EnInt..82...69V |url=https://hal-univ-rennes1.archives-ouvertes.fr/hal-01162374/file/Pyrethroid%20insecticide%20exposure.pdf}}</ref>


=== In domestic animals === === In domestic animals ===
Cases of toxicity have been observed in ], following use of agricultural deltamethrin preparation in external application in ] control. Symptoms appeared 36 hours after the application, and included muscular tremors that lead to ] 12 hours later. After 12 hours, there was spontaneous recovery and the animal could stand up again, although the muscular tremors persisted. The ] was then 38.3°C. (normal range 38.0 to 39.5°C.).{{Citation needed|date=September 2008}} Cases of toxicity have been observed in cattle, following use of agricultural deltamethrin preparation in external application for ] control.{{citation needed|date=February 2015}}


==References== ==References==
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==External links== ==External links==
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{{Insecticides}} {{Insecticides}}


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