Epoxiconazole

from Wikipedia, the free encyclopedia
Structural formula
Epoxiconazole
1: 1 mixture ( racemate ) of the two enantiomers shown
General
Non-proprietary name Epoxiconazole
other names
  • (2 RS , 3 SR ) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1 H -1,2,4-triazole
  • (2 R *, 3 S *) - 1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1 H -1,2,4-triazole
Molecular formula C 17 H 13 ClFN 3 O
External identifiers / databases
CAS number
  • 133855-98-8 [racemate with (2 RS , 3 SR ) configuration]
  • 135319-73-2 (mixture of four isomers)
EC number 406-850-2
ECHA InfoCard 100.100.840
PubChem 57484772
ChemSpider 24751862
Wikidata Q411326
properties
Molar mass 329.76 g mol −1
Physical state

firmly

density

1.374 g cm −3

Melting point

134 ° C

Vapor pressure

0.01 mPa (25 ° C)

solubility
  • practically insoluble in water (8.42 ppm, at 20 ° C)
  • soluble in acetone (140 g / l at 20 ° C)
  • soluble in ethyl acetate (100 g / l at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 351-360Df-411
P: 201-273-308 + 313-391-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Epoxiconazole is a fungicidal active ingredient from the triazole class that was developed to protect crops . This active ingredient inhibits the metabolism of various harmful fungi that can attack crops and thus prevents their growth . Epoxiconazole also inhibits the formation of conidia (mitospores) and can thereby limit the spread of the pathogens. Epoxiconazole was brought onto the market by BASF in 1993 . Since then it has been used individually or in a mixture with other active ingredients in many products to combat numerous pathogens to cereals . The crops in which epoxiconazole is used include, for example, cereals (predominantly wheat , barley , rye and triticale ), soybeans , bananas , rice , coffee and sugar beets .

commitment

Septoria leaf drought ( Septoria tritici )

The cereal diseases Septoria leaf drought ( Septoria tritici ) and brown rust ( Puccinia triticina ) are responsible for up to 30% of crop failures. If these diseases are not combated effectively, the availability of wheat and other grasses such as barley as well as the quality of the food made from the grain will be impaired .

resistance

Certain plant pathogens develop resistance to fungicides . In contrast to the relatively rapidly developing resistance to strobilurins , azole fungicides such as epoxiconazole have been able to maintain their effectiveness against the most important cereal diseases for over 20 years. According to a study by the Home Grown Cereals Authority (HGCA), epoxiconazole is one of the two triazole fungicides (alongside prothioconazole ) that still has strong eradicative and protective effects against Septoria tritici . In addition, farmers have additional classes of fungicides such as B. contact fungicides, strobilurins or carboxamides are available. The best effect is achieved with triazole mixtures.

Mode of action

As an azole, epoxiconazole inhibits the metabolism of harmful fungi and thus prevents their growth and spore formation. It blocks an important enzyme in fungi , lanosterol demethylase , which is involved in the formation of ergosterol , an essential part of the fungal cell membrane . Epoxiconazole has an eradicative effect by encapsulating fungal haustoria and cutting it off from the nutrient supply. This causes the haustoria to die. In addition, a positive influence on enzymes of the plant's own defense system ( chitinase , β-1,3-glucanase ), which attack the cell wall of harmful fungi, could be demonstrated. Some fungi impair the quality of the harvest by forming so-called mycotoxins . It has been shown that the use of triazoles such. B. Epoxiconazole in fungicide mixtures can significantly reduce such mytoxin levels.

Admission status

The EU Directive 91/414 / EEC on the placing of plant protection products on the market currently lists epoxiconazole in Annex I. Only the active ingredients listed there may be used in plant protection products and sold to farmers. Active substances can only be listed in Annex I after the EU authorities and EFSA have assessed extensive data on their physical and chemical properties, behavior and fate in the environment as well as toxicological properties. Only the proof that the active ingredient is harmless to users, consumers and the environment when used properly, enables the active ingredient to be included in Annex I. The active ingredients are included in Annex I for 10 years. The current inclusion of epoxiconazole runs until April 30, 2019. Farmers in the EU can use products containing epoxiconazole at least until the expiry date of the listing in Annex I, depending on the national approval. The approval was not extended and expired on April 30, 2020.

At the end of May 2019, France banned the sale and use of epoxiconazole because of its potentially harmful or carcinogenic effects in humans.

Individual evidence

  1. ↑ a b c Datasheet Epoxiconazole from Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
  2. ↑ a b c d e EPA Pesticide Fact Sheet (PDF).
  3. ↑ Müller, F .; Ackermann, P .; Margot, P .: Fungicides, Agricultural, 2. Individual Fungicides in Ullmanns Enzyklopädie der Technischen Chemie , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .
  4. ↑ Entry on epoxiconazole in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  5. ↑ Entry on (2RS, 3RS) -3- (2-chlorophenyl) -2- (4-fluorophenyl) - [(1H-1,2,4-triazol-1-yl) methyl] oxirane Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ XY Zhang, C Loyce, JM Meynard, S Savary: Characterization of multiple disease systems and cultivar susceptibilities for the analysis of yield losses in winter wheat. In: Crop Protection. No. 25, 2006, pp. 1013-1023, doi: 10.1016 / j.cropro.2006.01.013 .
  7. ^ New Challenges for Triazoles. Farmers Journal, Crop Protection ( English , PDF; 474 kB) McCabe T. 2004. Archived from the original on July 22, 2011. Retrieved on May 7, 2011.
  8. ^ Research and Development, Annual Project Report. Project number: RD-2004-3025. Fungicide performance network. Up to date information on fungicide performance for wheat growers. (No longer available online.) HGCA (Home Grown Cereals Authority), 2007, archived from the original on June 6, 2007 ; accessed on May 7, 2011 .
  9. ^ T. McCabe: The wheat disease management guide. (No longer available online.) HGCA (Home Grown Cereals Authority), 2010, archived from the original on July 11, 2011 ; accessed on May 7, 2011 .
  10. ↑ X. Xu, P. Nicholson, A. Ritieni: Effects of fungal interactions among Fusarium head blight pathogens on disease development and mycotoxin accumulation. In: International Journal of Food Microbiology No. 119 (1-2), 2007, pp. 67-71, doi: 10.1016 / j.ijfoodmicro.2007.07.027 .
  11. ↑ Commission Directive 2008/107 / EC of November 25, 2008 amending Council Directive 91/414 / EEC to include the active substances abamectin, epoxiconazole, fenpropimorph, fenpyroximate and tralkoxydim (text with EEA relevance) , accessed on 7 November 2008 May 2011 .
  12. ↑ BVL - Revoked and dormant approvals (last change: June 5, 2020) - Revocation of the approval of plant protection products with the active ingredient epoxiconazole on April 30, 2020. Accessed on June 18, 2020 .
  13. ↑ epoxyconazole ( French ) French Agency for Food, Environmental and Occupational Health & Safety. Retrieved June 1, 2019.