Cyromazine
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| Names | |
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| IUPAC name
N-Cyclopropyl-1,3,5-triazine-2,4,6-triamine
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| Other names
Citation
Larvadex Trigard Vetrazin | |
| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.060.215 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H10N6 | |
| Molar mass | 166.19 g/mol |
| Appearance | Crystalline |
| Melting point | 219 to 222 °C (426 to 432 °F; 492 to 495 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyromazine is a triazine insect growth regulator used as an insecticide to control dipterans and some other insects. It is a cyclopropyl derivative of melamine. The exact mechanism of action of cyromazine against insects is unclear although it does affect the larval and pupal cuticles.[2]
In veterinary medicine, cyromazine is used as an ectoparasiticide. It has been used since 1979 in Australia and New Zealand to control and prevent flystrike of sheep by blowfly.[3] The exact mechanism of action has not been determined but it is non-toxic to mammals and does not target the nervous system[3]. It is not toxic to adult flys only having its effect on larval forms by disrupting the moulting process and can give 8-10 weeks protection when applied topically.[4] Because of this it has little effect on existing infestations and is commonly used prophylactically. In 2011 resistance was detected in Lucilia cuprina to cyromazine from infested sheep that failed to be protected following treatment.[5]
Regulation
[edit]The Food Safety and Inspection Service (FSIS) of the United States Department of Agriculture (USDA) provides a test method for analyzing cyromazine and melamine in animal tissues in its Chemistry Laboratory Guidebook which "contains test methods used by FSIS Laboratories to support the Agency's inspection program, ensuring that meat, poultry, and egg products are safe, wholesome and accurately labeled."[6][7] In 1999, in a proposed rule published in the Federal Register regarding cyromazine residue, the United States Environmental Protection Agency (EPA) proposed "remov[ing] melamine, a metabolite of cyromazine from the tolerance expression since it is no longer considered a residue of concern."[8]
References
[edit]- ^ Merck Index, 12th Edition, 2845.
- ^ Bel, Yolanda; Wiesner, Petra; Kayser, Hartmut (October 2000). "Candidate target mechanisms of the growth inhibitor cyromazine: Studies of phenylalanine hydroxylase, puparial amino acids, and dihydrofolate reductase in dipteran insects". Archives of Insect Biochemistry and Physiology. 45 (2): 69–78. doi:10.1002/1520-6327(200010)45:2<69::AID-ARCH3>3.0.CO;2-3. ISSN 0739-4462.
- ^ a b Sandeman, R.M.; Levot, G.W.; Heath, A.C.G.; James, P.J.; Greeff, J.C.; Scott, M.J.; Batterham, P.; Bowles, V.M. (October 2014). "Control of the sheep blowfly in Australia and New Zealand – are we there yet?". International Journal for Parasitology. 44 (12): 879–891. doi:10.1016/j.ijpara.2014.08.009.
- ^ Tellam, R.L.; Bowles, V.M. (March 1997). "Control of blowfly strike in sheep: Current strategies and future prospects". International Journal for Parasitology. 27 (3): 261–273. doi:10.1016/S0020-7519(96)00174-9.
- ^ Levot, Gw (November 2012). "Cyromazine resistance detected in A ustralian sheep blowfly". Australian Veterinary Journal. 90 (11): 433–437. doi:10.1111/j.1751-0813.2012.00984.x. ISSN 0005-0423.
- ^ "CYROMAZINE AND MELAMINE" (PDF). USDA FSIS. July 1991. Archived from the original (PDF) on 2007-06-16. Retrieved 2007-04-27.
- ^ "Chemistry Laboratory Guidebook". USDA FSIS. Retrieved 2007-04-27.
- ^ Environmental Protection Agency. Cyromazine; Pesticide Tolerance