Amitraz
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| General | |||||||||||||||||||
| Non-proprietary name | Amitraz | ||||||||||||||||||
| other names |
1,5-di- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-dione-bis- N , N - (dimethyl-2,4-phenyliminomethyl) - N - methylamine |
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| Molecular formula | C 19 H 23 N 3 | ||||||||||||||||||
| Brief description |
white to pale yellow crystalline substance |
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| Drug information | |||||||||||||||||||
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| Mechanism of action |
Octopamine receptor antagonist |
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| properties | |||||||||||||||||||
| Molar mass | 293.41 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
86-87 ° C |
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| solubility |
practically insoluble in water (<1 mg l −1 at 25 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Amitraz is a drug from the group of amidines and is used in veterinary medicine as a remedy against ectoparasites such as mites and insects . The substance is also used as an insecticidal active ingredient in plant protection products.
synthesis
Two routes are available for the synthesis of amitraz.
Path 1: 2,4-xylidine + triethyl orthoformate + methylamine
The first step in this reaction path is the reaction of the aniline derivative 2,4-xylidine with triethyl orthoformate . In the next step, methylamine is added, liberating ethanol. In the end, two molecules of N -2,4-dimethyl- N -methylformamidine react with one another, splitting off methylamine to form amitraz.
Path 2: N -methylformamide + 2,4-xylidine:
The first step is the reaction of N -methylformamide with 2,4-dimethylaniline . The reaction is catalyzed by carboxylic acid halides or p -toluenesulfonic acid chloride . In the second step, two molecules of the same intermediate product condense as in 1 with elimination of methylamine to form amitraz.
Analytics
For the reliable qualitative and quantitative determination of Amitraz, coupling methods of gas chromatography and HPLC with mass spectrometry are used. The examination items, such as As urine, fruit or honey make special methods of sample preparation required.
effect
Amitraz is an antagonist of the receptors for octopamine in the parasite's brain. The active ingredient causes overexcitability and thus ultimately paralysis and death of the parasites.
In mammals, only a small part (10%) is absorbed through the skin . Amitraz administered intravenously is rapidly broken down in the liver and excreted via the kidneys .
application
Veterinary medicine
Amitraz can be used on many pets in the form of a bath or washing solution against mites , ticks or animal lice . The effectiveness against fleas is only mediocre. Horses, cats and rodents are particularly sensitive to amitraz, so that use on these animals is not recommended.
At the moment, however, Amitraz is only approved for domestic dogs and for the treatment of varroosis in honey bees ( Apis mellifera ) in Germany. For demodicosis it was the method of choice for many years. However, Chihuahuas , pregnant or lactating bitches, and puppies must not be treated with Amitraz.
When used externally, Amitraz is well tolerated. The side effects result from an agonistic effect on the α 2 -adrenoceptor and range from inappetence , vomiting , drop in blood pressure and slowed heart rate to depression . As an antidote to atipamezole or yohimbine be used.
Plant protection
In Switzerland, plant protection products were available that contained amitraz as an acaricidal active ingredient. They could be used against pear leaf suckers and spider mites in pome fruit. In commercial horticulture, they were allowed to be used against spider mites and red spiders on cut flowers, perennials and potted plants. Amitraz is dangerous for bees and was therefore not allowed to be used on flowering plants. Today in the EU states including Germany and Austria as well as in Switzerland no pesticides with Amitraz are allowed anymore.
Trade names
In veterinary medicine, Amitraz is approved in Germany as a monopreparation for the treatment of beehives (trade name Apivar , or Apitraz ) against varroa mites . The preparation to the washing treatment of dogs ( Ectodex ) is indeed marketable, but no longer commercially available. Until August 31, 2010, a vermin neck soon based on the active ingredient was also approved. There is also a combination preparation with fipronil and methoprene ( Certifect ). The combination with metaflumizone ( ProMeris Duo ) is marketable , but no longer on the market (as of December 11, 2017).
Individual evidence
- ↑ a b c d Entry on Amitraz. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
- ↑ a b Entry on Amitraz in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
- ↑ Entry on Amitraz in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ PM Brown: Toxicological problems associated with the manufacture of triazapentadienes . In: Proceedings of the Royal Society of Medicine . tape 70 , no. 1 , 1977, pp. 41-43 , PMC 1542871 (free full text).
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 836 ( limited preview in Google Book search).
- ↑ X. Gao, Y. Tan, H. Guo: Simultaneous determination of amitraz, chlordimeform, formetanate and their main metabolites in human urine by high performance liquid chromatography-tandem mass spectrometry. In: J Chromatogr B Analyt Technol Biomed Life Sci. 1052, May 1, 2017, pp. 27–33. PMID 28346886 .
- ↑ N. Tokman, C. Soler, M. Farré, Y. Picó, D. Barceló: Determination of amitraz and its transformation products in pears by ethyl acetate extraction and liquid chromatography-tandem mass spectrometry. In: J Chromatogr A. 1216 (15), Apr 10, 2009, pp. 3138-3146. PMID 19232624 .
- ↑ M. Caldow, RJ Fussell, F. Smith, M. Sharman: Development and validation of an analytical method for total amitraz in fruit and honey with quantification by gas chromatography-mass spectrometry. In: Food Addit Contam. 24 (3), Mar 2007, pp. 280-284. PMID 17364930 .
- ↑ a b c Entry on Amitraz at Vetpharm .
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Amitraz in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 11, 2016.
- ↑ vetidata (only accessible to experts).
Web links
- Entry on osaterone acetate at Vetpharm, accessed on August 11, 2012.
