Mandestrobin

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Structural formula
Structural formula without stereochemistry
Simplified structural formula without stereochemistry
1: 1 mixture of the ( R ) - and the ( S ) -form
General
Surname Mandestrobin
other names
  • ( RS ) -2-methoxy- N -methyl-2- [α- (2,5-xylyloxy) - o -tolyl] acetamide
  • (±) -2-Methoxy- N -methyl-2- [α- (2,5-xylyloxy) - o -tolyl] acetamide
Molecular formula C 19 H 23 NO 3
Brief description

white to pale yellow solid

External identifiers / databases
CAS number
  • 173662-97-0 ( racemate )
  • 394657-24-0 [( R ) -form]
  • 1229001-61-9 [( S ) -form]
EC number 695-819-9
ECHA InfoCard 100.224.551
PubChem 10935908
ChemSpider 9111144
Wikidata Q27156687
properties
Molar mass 313.39 g mol −1
Physical state

firmly

Melting point

102 ° C

boiling point

296 ° C

Vapor pressure

2.26 · 10 −8  Pa (20 ° C)

solubility
  • practically insoluble in water (15.8 mg l −1 at 20 ° C)
  • Easily soluble in acetone (310 g l −1 at 20 ° C) and dichloromethane (480 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances
09 - Dangerous for the environment

Caution

H and P phrases H: 315-317-319
P: 280-305 + 351 + 338
Toxicological data
  • > 2000 mg kg −1 ( LD 50 ,  rat ,  oral )
  • > 2225 mg kg −1 ( LD 50 , bird ( Colinus virginiamus ) ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mandestrobin is a synthetic fungicide from the strobilurin class of substances and is used in agriculture. It was launched by Sumitomo Chemical in 2013 and is marketed as a racemate [1: 1 mixture of the ( R ) and ( S ) form].

presentation

Mandestrobin can be formed from dichloromethyl-2-chloromethylbenzene in a multi-stage reaction. The manufacturer Sumitomo also specifies other synthetic routes with inexpensive starting materials such as o -xylene , toluene and phthalide .

Properties and structure

Mandestrobin is a white to light yellow solid. It is not volatile and only sparingly soluble in water. With a half-life of 140 days, it only degrades very slowly in the soil. It is relatively susceptible to photolysis with a half-life of 4.5 days.

The molecule has a stereocenter . Two different isomers are therefore possible. The fungicide mandestrobin is used as a racemate . The pure enantiomers

  • ( R ) -2-methoxy- N -methyl-2- [α- (2,5-xylyloxy) - o -tolyl] acetamide and
  • ( S ) -2-methoxy- N -methyl-2- [α- (2,5-xylyloxy) - o -tolyl] acetamide

have practically no meaning.

Mode of action and use

The mode of action of mandestrobin is analogous to other strobilurins. It inhibits cell respiration in the mitochondria by interfering with the electron transport in the cytochrome bc complex and thereby preventing ATP production. Due to this mode of action, Mandestrobin has a broad spectrum of activity.

Mandestrobin has a systemic effect and can be used in agriculture for cereals and rapeseed as well as in fruit growing. The areas of application include white stalk and fruit rot .

toxicology

In animal experiments on rats, mandestrobin is neither orally nor dermally or inhalatively acutely toxic . It does not irritate skin or eyes and is not a skin sensitizer. In addition, no genotoxic or carcinogenic potential could be determined. The European Food Safety Authority (EFSA) set the permitted daily dose at 0.19 mg / kg body weight. Due to the low toxic potential, no acute reference dose has been established.

The EFSA classifies the risk of poisoning of birds, wild animals and insects as low. On the other hand, there is a high risk for aquatic life.

Admission

Mandestrobin was approved by the European Union on December 9, 2015. Plant protection products containing this active ingredient are available in Germany and Austria, although use is limited to rapeseed cultivation. There are no approved preparations in Switzerland.

Individual evidence

  1. ↑ a b c d e f g h i j k Entry on Mandestrobin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on September 3, 2019.
  2. ↑ a b SAFETY DATA SHEET Mandestrobin. (PDF) HPC Standards GmbH, February 19, 2019, accessed on September 3, 2019 .
  3. ↑ Peter Jeschke, Matthias Witschel, Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2019, ISBN 978-3-527-34089-7 ( limited preview in Google Book Search [accessed August 5, 2019]).
  4. ↑ Dai Hirotimi, et al .: Research and Development of a Novel Fungicide 'Mandestrobin'. (PDF) In: Sumitomo. Accessed January 16, 2020 (English).
  5. ↑ Heitefuss, Rudolf .: Plant protection: Fundamentals of practical phytomedicine; 22 tables . 3., rework. and exp. Aufl. Thieme, Stuttgart 2000, ISBN 3-13-513303-6 ( limited preview in the Google book search [accessed February 20, 2020]).
  6. ^ Clemens Lamberth, Jürgen Dinges: Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals . John Wiley & Sons, 2016, ISBN 978-3-527-33947-1 ( limited preview in Google Book Search [accessed February 20, 2020]).
  7. ↑ Conclusion on the peer review of the pesticide risk assessment of the active substance mandestrobin . In: EFSA Journal . tape 13 , no. 5 , 2015, ISSN  1831-4732 , p. 4100 , doi : 10.2903 / j.efsa.2015.4100 .
  8. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on mandestrobin in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on January 16, 2020.