Aklonifen - a herbicide from the group of diphenyl ethers. It was originally developed by the German company Celamerck from Ingelheim and appeared on the market around 1983. Later, a patent for production through a number of intermediaries passed to Bayer CropScience. The patent is currently expired.
| Aklonifen | |
|---|---|
| Are common | |
| Systematic name | 2-chloro-6-nitro-3-phenoxyaniline |
| Chem. formula | C 12 H 9 ClN 2 O 3 |
| Physical properties | |
| Molar mass | 264.67 g / mol |
| Density | 1.46 g / cm³ |
| Thermal properties | |
| T. melt. | 80–81 ° C |
| Chemical properties | |
| Solubility in water | practically insoluble in water [1] |
| Solubility in | soluble in methanol and hexane [2] |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| ChemSpider | |
| Security | |
| LD 50 | > 6500 mg · kg −1 (rat, oral) [3]
|
| R phrases | R50 / 53 |
| S-phrases | S60 S61 |
| H phrases | H351 , H317 , H410 |
| P-phrases | P273 , P501 |
| GHS icons |    |
Content
Synthesis
It is synthesized by condensation of 2,3-dichloro-6-nitroaniline with phenol . 2,3-Dichloro-6-nitroaniline, in turn, is a reaction product of 1,2,3-trichloro-4-nitrobenzene and ammonia [4] [5] .
Physical Properties
Aklonifen is a powder of yellow crystals, but it is usually sold in liquid form as a suspension concentrate, which must be mixed with water and sprayed. It is used against annual grassy and broad-leaved weeds.
Usage
Aklonifen is used as a plant protection product, and as such is approved in Germany, Austria, Switzerland, Ukraine and many other European countries [6] . Sold under the trade name Bandur [7] and Challenge. The mechanism of action is based on impaired synthesis of carotenoids , and selective inhibition of protoporphyrinogen oxidase is an important enzyme in the pathway of chlorophyll synthesis. Effective against herbs and broad-leaved weeds [8] .
Toxicity
Aklonifen has low acute toxicity. According to the results of the study, it was proposed to classify it as an irritating substance, harmful and possibly carcinogenic (category 3). Affected rats showed brain tumors [9] .
Moderately persistent substance, in the soil the half-life is from 30 to 130 days; in water, on the contrary, it is very stable and does not hydrolyze at pH values from 5 to 9. It is also very toxic to aquatic organisms, and therefore is classified as an environmentally hazardous substance [10] .
Notes
- ↑ Datenblatt Aclonifen bei Sigma-Aldrich , abgerufen am 23. Mai 2011 ( PDF ).
- ↑ Ullmann's Agrochemicals, Band 1, Seite 784; ISBN 978-3-527-31604-5 .
- ↑ 1 2 Record of 2-Chlor-6-nitro-3-phenoxyanilin in the GESTIS Substance Database of the IFA .
- ↑ Duits octrooi DE 2831262, "2-chlor-6-nitroaniline" van 31 januari 1980 aan Celamerck GmbH.
- ↑ Patent DE2831262 : 2-Chlor-6-nitroaniline.
- ↑ Generaldirektion Gesundheit und Lebensmittelsicherheit der Europäischen Kommission: Eintrag zu Aclonifen in der EU-Pestiziddatenbank ; Eintrag in den nationalen Pflanzenschutzmittelverzeichnissen der Schweiz (unavailable link) , Österreichs und Deutschlands ; abgerufen am 19.
- ↑ Bayer CropScience: Bandur
- ↑ Kilinc Özgür , Reynaud Stéphane , Perez Laurent , Tissut Michel , Ravanel Patrick. Physiological and biochemical modes of action of the diphenylether aclonifen // Pesticide Biochemistry and Physiology. - 2009. - February ( t. 93 , No. 2 ). - S. 65-71 . - ISSN 0048-3575 . - DOI : 10.1016 / j.pestbp.2008.11.00.00 .
- ↑ Conclusion regarding the peer review of the pesticide risk assessment of the active substance aclonifen (Juli 2008)
- ↑ Richtlijn 2013/39 / EU van 12 augustus 2013 tot wijziging van Richtlijn 200/60 / EG en Richtlijn 2008/105 / EG wat betreft prioritaire stoffen op het gebied van het waterbeleid. Publicatieblad L226 van 24 augustus 2013 blz. one