Amitraz

Amitraz
Ball-and-stick model of the amitraz molecule
Names
IUPAC name
N,N'-[(Methylimino)dimethylidyne]di-2,4-xylidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.691 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+ checkY
    Key: QXAITBQSYVNQDR-ZIOPAAQOSA-N checkY
  • InChI=1/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+
    Key: QXAITBQSYVNQDR-ZIOPAAQOBL
  • N(=C/N(\C=N\c1ccc(cc1C)C)C)\c2ccc(cc2C)C
Properties
C19H23N3
Molar mass 293.41 g/mol
Melting point 86 to 87 °C (187 to 189 °F; 359 to 360 K)
Insoluble
Vapor pressure 2.6 x 10−6 mmHg
Pharmacology
QP53AD01 (WHO)
Legal status
  • AU: S6 (Poison)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Amitraz (development code BTS27419) is a non-systemic acaricide and insecticide[1] and has also been described as a scabicide. It was first synthesized by the Boots Co. in England in 1969.[2] Amitraz has been found to have an insect repellent effect, works as an insecticide and also as a pesticide synergist.[3] Its effectiveness is traced back on alpha-adrenergic agonist activity, interaction with octopamine receptors of the central nervous system and inhibition of monoamine oxidases and prostaglandin synthesis.[4] Therefore, it leads to overexcitation and consequently paralysis and death in insects. Because amitraz is less harmful to mammals, amitraz is among many other purposes best known as insecticide against mite- or tick-infestation of dogs.[1] It is also widely used in the beekeeping industry as a control for the Varroa destructor mite, although there are recent reports of resistance (driven by overuse and off label use).[citation needed]

  1. ^ a b Corta, E., Bakkali, A., Berrueta, L. A., Gallo, B., & Vicente, F. (1999). Kinetics and mechanism of amitraz hydrolysis in aqueous media by HPLC and GC-MS. Talanta, 48(1), 189-199
  2. ^ Harrison, I. R., et al. (1973). 1,3,5-Triazapenta-1, 4-dienes: Chemical aspects of a new group of pesticides. Pestic. Sci. 4: 901
  3. ^ PubChem Substance. Amitraz – Substance Summary. retrieved from https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=24868774#x332
  4. ^ Cite error: The named reference Bonsall was invoked but never defined (see the help page).