Acetamiprid
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| Surname | Acetamiprid | |||||||||||||||
| other names |
( E ) - N 1 - [(6-chloro-3-pyridyl) methyl] - N 2 -cyano- N 1 -methylacetamidine ( IUPAC ) |
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| Molecular formula | C 10 H 11 ClN 4 | |||||||||||||||
| Brief description |
white to slightly yellowish, powdery, odorless solid |
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| properties | ||||||||||||||||
| Molar mass | 222.68 g · mol -1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
98.9 ° C |
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| Vapor pressure |
<1 · 10 −6 Pa (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 . | ||||||||||||||||
Acetamiprid is a heterocyclic aromatic chemical compound that is used as an insecticide and belongs to the group of neonicotinoids . Acetamiprid -containing insecticides are sold on the market, particularly under the trade name Careo .
Presentation and extraction
The synthesis starts with the reaction of trimethyl orthoacetate with cyanamide with the formation of the intermediate compound methyl N -cyanoacetimidate. The reaction with 3-aminomethyl-6-chloropyridine and subsequent methylation using dimethyl sulfate lead to the target compound. Alternatively, the reaction with 6-chloro-3- (methylamino) methylpyridine gives the acetamiprid directly.
use
Acetamiprid is used as an insecticidal active ingredient in crop protection products. It is suitable for the control of biting and sucking insects such as scale insects , moth sign lice (uA whitefly), fungus gnats , cydalima perspectalis and mealybugs . In Germany, Austria and Switzerland, the approved products are mostly intended for the treatment of potted and ornamental plants. However, it is also approved in vegetable cultivation, for example on cucumber, tomato and salads, and to control aphids on pome fruit . Acetamiprid is also highly effective against the larvae of the cherry fruit fly and is therefore approved for commercial cherry cultivation in Switzerland and Austria. In arable farming, individual preparations can also be used against the rapeseed beetle or the larvae of the Colorado potato beetle . Acetamiprid comes in the form of “plant sticks”, as a spray, granulate or concentrate. It is approved as an active ingredient in plant protection products in many EU countries , including Germany and Austria, as well as Switzerland.
regulation
The use of acetamiprid is approved in the EU and 26 member states. The permitted daily dose , the acute reference dose and the acceptable user exposure are each 0.025 milligrams per kilogram of body weight and day.
The European Food Safety Authority (EFSA) proposed in December 2013 that the permitted daily dose, the acute reference dose and the acceptable user exposure be reduced from 0.07 mg / kg to 0.025 mg / kg body weight due to possible effects on the developing nervous system.
In 2016, the limit values for acetamiprid in various foods were raised by EFSA. For example, for olives from 0.1 mg / kg to 0.9 mg / kg, wheat from 0.03 mg / kg to 0.1 mg / kg or tomatoes from 0.2 mg / kg to 0.5 mg / kg .
In Switzerland there is a tolerance value of 0.5 mg / kg for lettuce, 0.1 mg / kg for peas, leek, pome fruit and cherries and 0.05 mg / kg for potatoes, onions, plums and plums.
Individual evidence
- ↑ a b c US EPA : Pesticide Fact Sheet Acetamiprid
- ↑ a b c d Tomio Yamada, Hidemitsu Takahashi, Renpei Hatano: A Novel Insecticide, Acetamiprid in “Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor”, Ed. Izuru Yamamoto, John E. Casida, Springer-Verlag 1999, ISBN 978-4-431-68011-6 , pp. 149-176.
- ↑ a b Entry on acetamiprid in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
- ↑ Entry on (E) -N1 - [(6-chloro-3-pyridyl) methyl] -N2-cyano-N1-methylacetamidine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturer or . marketer can use the harmonized classification and labeling expand .
- ↑ Acetamiprid PESTANAL data sheet from Sigma-Aldrich , accessed on October 24, 2016 ( PDF ).
- ↑ From Buchsbaumzuensler.net, accessed on August 31, 2016
- ↑ a b Directorate-General for Health and Food Safety of the European Commission: Entry on acetamiprid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
- ↑ EFSA: EFSA assesses possible association between two neonicotinoids and developmental neurotoxicity , press release of December 17, 2013.
- ↑ EFSA: EFSA increases limit values for acetamiprid , EFSA Journal of February 16, 2016.
- ↑ Federal Department of the Interior: Ordinance on foreign substances and ingredients in food (Foreign and Ingredients Ordinance, FIV) (PDF; 543 kB) .