Etoxazole

Last updated
Etoxazole
Etoxazol Grundstruktur V2.svg
Etoxazole.png
Names
IUPAC name
2-(2,6-Difluorophenyl)-4-[2-ethoxy-4-(2-methyl-2-propanyl)phenyl]-4,5-dihydro-1,3-oxazole
Other names
(R,S)-5-tert-butyl-2-[2,6-difluorophenyl)-4,5-dihydro-1,3-oxazol-4-yl]phenetole [1]
Identifiers
3D model (JSmol)
8930214
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.107.983 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 604-891-2
KEGG
PubChem CID
UNII
  • InChI=1S/C21H23F2NO2/c1-5-25-18-11-13(21(2,3)4)9-10-14(18)17-12-26-20(24-17)19-15(22)7-6-8-16(19)23/h6-11,17H,5,12H2,1-4H3
    Key: IXSZQYVWNJNRAL-UHFFFAOYSA-N
  • CCOc1cc(ccc1C2COC(=N2)c3c(cccc3F)F)C(C)(C)C
Properties
C21H23F2NO2
Molar mass 359.417 g·mol−1
Appearancecolorless crystalline powder with a musty odor [1]
Density 1.238 [1]
Melting point 101.5–102.5°C [1]
insoluble in H2O, slightly soluble in hexane, n-heptane, soluble in MeOH, EtOH, acetone, cyclohexanone, THF, MeCN, EtOAc, xylene. [1]
log P Kow 5.59 [1]
Vapor pressure 7 mPa @ 25°C [1]
Hazards
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Etoxazole is a narrow spectrum systemic acaricide used to combat spider mites. It targets a variety of mites in the egg, larvae and nymph stages however not the adult stage. It also exhibits insecticidal activity towards aphids, the green rice leafhopper and diamondback moth. The mode of action has been shown to inhibit chitin synthase (IRAC group 10B). [2] Resistance due to its high efficacy and cross resistance when used with other acaricides are both of concern similar to was seen in the fast development of cross resistance in the previous generation of acaricides. The LC50 for resistant mite strains has been observed over 100,000 times greater than that of susceptible strains. Thus resistance management strategies are important in order to limit the increase of etoxazole resistant mite strains. [3] [4]

Contents

Etoxazole has a mammalian toxicity LD50 of 5 g/kg and an environmental persistence DT50 of 19 days. [5] Toxicity towards fish is of potential concern.

Etoxazole was discovered in the 1980s by Yashima and was released for commercial use in 1998 in Japan. It is sold under various commercial preparations for crop application such as TetraSan 5 WDG [6] and Zeal by Valent in the United States.

Stereoisomerism

Etoxazole
(2 stereoisomers)
(S)-Etoxazol V2.svg
(S)-configuration
(R)-Etoxazol V2.svg
(R)-configuration

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References

  1. 1 2 3 4 5 6 7 Müller, Franz; Streibert, Hans Peter; Farooq, Saleem (2009). Acaricides. doi:10.1002/14356007.a01_017.pub2. ISBN   978-3527306732.{{cite book}}: |journal= ignored (help)
  2. Douris, Vassilis; Steinbach, Denise; Panteleri, Rafaela; Livadaras, Ioannis; Pickett, John Anthony; Van Leeuwen, Thomas; Nauen, Ralf; Vontas, John (2016). "2016". Proceedings of the National Academy of Sciences. 113 (51): 14692–14697. doi: 10.1073/pnas.1618258113 . PMC   5187681 . PMID   27930336.
  3. Nauen, Ralf; Smagghe, Guy (2006-05-01). "Mode of action of etoxazole". Pest Management Science. 62 (5): 379–382. doi:10.1002/ps.1192. ISSN   1526-4998. PMID   16555232.
  4. Uesugi, R.; Goka, K.; Osakabe, M. H. (2002-12-01). "Genetic Basis of Resistances to Chlorfenapyr and Etoxazole in the Two-Spotted Spider Mite (Acari: Tetranychidae)". Journal of Economic Entomology. 95 (6): 1267–1274. doi: 10.1603/0022-0493-95.6.1267 . ISSN   0022-0493. PMID   12539841. S2CID   24716020.
  5. Dekeyser, Mark A (2005-02-01). "Acaricide mode of action". Pest Management Science. 61 (2): 103–110. doi:10.1002/ps.994. ISSN   1526-4998. PMID   15625668.
  6. "TetraSan 5 WDG product label" (PDF). Valent. 2011. Archived from the original (PDF) on 2018-04-11. Retrieved 2020-11-10.