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Record Information
Version3.6
Creation Date2012-09-13 11:44:47 UTC
Update Date2013-05-30 04:29:39 UTC
HMDB IDHMDB41866
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeltamethrin
DescriptionDeltamethrin is a pyrethroid ester insecticide. Deltamethrin plays 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. 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. This material is a member of one of the safest classes of pesticides: synthetic pyrethroids. 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. 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. 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. 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.
Structure
Thumb
Synonyms
  1. (S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
  2. Butox
  3. Cislin
  4. Crackdown
  5. Decamethrin
  6. Decamethrine
  7. Decis
  8. Decis 0.5ULV
  9. Decis 1.5ULV
  10. Decis 2.5ULV
  11. Dekametrin
  12. DeltaGard
  13. Deltagran
  14. Deltamethrin
  15. Deltamethrine
  16. Esbecythrin
  17. Glossinex 200
  18. K-Obiol
  19. K-Othrin
  20. K-Othrine
  21. New Musigie
  22. Phagase 1
  23. Suspend
  24. Zorcis
Chemical FormulaC22H19Br2NO3
Average Molecular Weight505.199
Monoisotopic Molecular Weight502.973168773
IUPAC Name(S)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional IUPAC Namedeltamethrin
CAS Registry Number52918-63-5
SMILES
[H][C@@](OC(=O)[C@]1([H])[C@]([H])(C=C(Br)Br)C1(C)C)(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1
InChI Identifier
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
InChI KeyOWZREIFADZCYQD-NSHGMRRFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassPyrethroids
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Pyrethroid insecticides(KEGG)
  • aromatic ether(ChEBI)
  • carboxylic ester(ChEBI)
  • nitrile(ChEBI)
  • organobromine compound(ChEBI)
Substituents
  • Benzyl Alcohol Derivative
  • Benzyl Cyanide
  • Benzyloxycarbonyl
  • Carboxylic Acid Ester
  • Cyclopropane
  • Halogen Derivative
  • Ketene Acetal Or Derivative
  • Nitrile
  • Organic Halide
  • Organobromide
Direct ParentPyrethroids
Ontology
StatusExpected and Not Quantified
Origin
  • Toxin/Pollutant
Biofunction
  • Nutrient
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point100 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2e-06 mg/mL at 25 °CNot Available
LogP6.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP6.13ALOGPS
logP5.74ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.29ChemAxon
Polarizability42.76ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID37079
KEGG Compound IDC10985
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkdeltamethrin
NuGOwiki LinkHMDB41866
Metagene LinkHMDB41866
METLIN IDNot Available
PubChem Compound40585
PDB IDNot Available
ChEBI ID4388
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available