Diflubenzuron
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| General | ||||||||||||||||
| Surname | Diflubenzuron | |||||||||||||||
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| Molecular formula | C 14 H 9 ClF 2 N 2 O 2 | |||||||||||||||
| Brief description |
white powder with a faint odor |
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| properties | ||||||||||||||||
| Molar mass | 310.69 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| density |
1.56 g cm −3 (20 ° C) |
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| Melting point |
230–232 ° C (decomposition) |
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| solubility |
practically insoluble in water |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Diflubenzuron is an insecticide from the group of benzamides and benzoylureas that acts as a chitin synthesis inhibitor. Important areas of application are the control of the mass occurrence of caterpillars in forestry or of mosquitoes. Diflubenzuron was developed in 1975 by the Dutch chemical company Philips-Duphar.
synthesis
Diflubenzuron is made from chlorophenyl isocyanate ( p -chloroaniline , phosgene ) and 2,6-difluorobenzamide .
effect
Diflubenzuron is absorbed by the larvae as they feed and inhibits the synthesis of chitin during molting . The cuticle of the larvae is not formed again, which leads to the death of the animals. The insecticide also works against insect eggs (ovicide) by interfering with the incorporation of chitin into the skin of the embryo. Diflubenzuron has no effect on adult insects ( adults ).
commitment
Diflubenzuron is marketed as a water- dispersible powder. In Switzerland, plant protection products containing diflubenzuron are approved for use against butterflies on ornamental trees and shrubs, in fruit growing and against cabbage whites and the coal owl in the cultivation of cabbage, but not in forestry. Diflubenzuron can also be used against fungus gnats in fungal cultures and against red-necked beetle and Oulema gallaeciana when growing cereals .
Admission
In accordance with European legislation (Directive 98/8 / EC on the placing of biocidal products on the market) and with Directive 2013/6 / EU of February 20, 2013, a decision has been made to add the active ingredient diflubenzuron to the corresponding list from February 1, 2015 (Appendix I of Directive 98/8 / EC) for product type 18 (insecticides). The sale of biocidal products that contain the active ingredient diflubenzuron is therefore permitted in the EU (Switzerland has adopted this provision) for product type 18 (insecticides) until December 31, 2018.
Diflubenzuron was approved in Germany for the control of various caterpillars in the forest and in the cultivation of ornamental plants as well as against the fungus gnat in mushroom cultures, but there is no longer a national approval.
In Austria, use in the forest and in the cultivation of pome fruit and ornamental plants was permitted. Here Diflubenzuron was used to combat the ever increasing chestnut leaf miner ( Cameraria ohridella ). There is no longer any approval in Austria either.
Ecotoxicology
Diflubenzuron was classified as not dangerous to bees . The lethal concentration (LC 50 ) for the rainbow trout was 140 mg / l in the 96-hour test. An EC 50 (49 hours) of 16 µg / l was found in the large water flea . The oral lethal dose (LD 50 ) for the red-shouldered blackbird was 3762 mg / kg body weight. The product is classified as harmful to populations of the common lacewing ( Chrysoperla carnea ) and the hover fly ( Episyrphus balteatus ).
literature
- W. Buchberger: Effects and side effects of Dimilin , Federal Research and Training Center for Forests, Natural Hazards and Landscape, 2000 ( Memento from July 3, 2013 in the Internet Archive )
- H. Doppelreiter & M. Korioth: Developmental inhibition by diflubenzuron in the soil termites Heterotermes indicola and Reticulitermes flavipes , Zeitschrift für Angewandte Entomologie, Vol. 91, 1981
Individual evidence
- ↑ a b c d e f g h Entry on diflubenzuron in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
- ↑ Entry on diflubenzuron. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.
- ↑ Benzoylurea insecticides and other pesticides in pome fruit ( Memento from October 15, 2007 in the Internet Archive )
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 226 (English, limited preview in Google Book search).
- ^ Diflubenzuron, Extension Toxicology Network .
- ↑ a b Werner Perkow: Active Ingredients of Plant Protection and Pesticides , 2nd Edition, 3rd Erg. Current issue March 1992, Paul Parey publishing house.
- ↑ a b c Directorate General for Health and Food Safety of the European Commission: Entry on diflubenzuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland and Germany ; accessed on March 12, 2016.
- ↑ Directive 98/8 / EC of February 16, 1998 on the placing of biocidal products on the market . In: Official Journal of the European Communities . L, No. 123, April 24, 1998, pp. 1-63.
- ↑ Directive 2013/6 / EU of 20 February 2013 amending Directive 98/8 / EC to include in Annex I of diflubenzuron . In: Official Journal of the European Communities. L, No. 48, February 21, 2013, pp. 10-13.
- ↑ Study by the Federal Environment Agency on the use of pesticides and biocidal products. Vienna 2001.