Cyprodinil

Structural formula
General
Surname	Cyprodinil
other names	4-Cyclopropyl-6-methyl- N- phenylpyrimidin-2-amine
Molecular formula	C 14 H 15 N 3
Brief description	white to beige solid
External identifiers / databases
CAS number 121552-61-2 EC number 601-785-8 ECHA InfoCard 100.124.179 PubChem 86367 ChemSpider 77885 Wikidata Q3008902
properties
Molar mass	225.29 g mol −1
Physical state	firmly
density	1.21 g cm −3
Melting point	75.9 ° C
boiling point	> 360 ° C at 101.325 kPa
Vapor pressure	0.51 mPa (25 ° C)
solubility	practically insoluble in water soluble in ethanol and acetone
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 317-410 P: 273-280-305 + 351 + 338-333 + 313-391-501
Toxicological data	> 2000 mg kg −1 ( LD 50 ,  rat ,  oral ) > 2000 mg kg −1 ( LD 50 ,  rat ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyprodinil is a chemical compound from the group of the anilino-pyrimidines .

Extraction and presentation

Cyprodinil can be obtained by reacting phenylguanidine with the β-diketone 1-cyclopropyl-butane-1,3-dione . The latter is in turn represented by a Claisen condensation of methyl acetate with methylcyclopropyl ketone .

properties

Cyprodinil is a white to, as a technical product, beige solid that is practically insoluble in water. It is stable to hydrolysis and photolysis .

use

Cyprodinil is a systemic broadband fungicide and is, for example, in wheat and rye against eyespot ( Pseudocercosporella herpotrichoides ) and in orchards against apple scab , and in the wine as a mixture with fludioxonil against Botrytis used. It is said to act as an inhibitor of methionine biosynthesis and disrupt the fungal life cycle by inhibiting mycelial growth. However, the FRAC cyprodinil no longer acts as a methionine synthesis inhibitor. It could act on the mitochondria instead.

Admission

Cyprodinil is approved for agriculture, horticulture and viticulture in many countries. It was launched in 1994.

With effect from May 1, 2007, the EU Commission added cyprodinil to the list of permissible active ingredients in plant protection products.

In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. Switch) containing this active ingredient are approved.

Residues in food

In Switzerland, blueberries , currants and gooseberries have a relatively high maximum residue level of 5 milligrams of cyprodinil per kilogram.

Individual evidence

1. ↑ ^{a b} Entry for CAS no. 121552-61-2 in the GESTIS substance database of the IFA , accessed on April 26, 2013(JavaScript required) (Warning: wrong Lemmaname at GESTIS).
2. ↑ ^{a b c d e} EPA: Pesticide Fact Sheet - Cyprodinil (PDF; 29 kB), April 6, 1998.
3. ↑ ^{a b c d} FAO: FAO Specifications and evaluations for agricultural pesticides CYPRODINIL (PDF; 167 kB)
4. ↑ 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 .
5. ^ ^{A b c} Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 706 ff . ( limited preview in Google Book search).
6. ↑ Entry on 4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
7. ↑ Data sheet Cyprodinil, PESTANAL at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
8. ↑ Rudolf Heitefuss: Plant protection: Basics of the practical Phytomedicin . Georg Thieme Verlag, 2000, ISBN 3-13-513303-6 , p. 153 ( limited preview in Google Book search).
9. ^ Andreas Mosbach, Dominique Edel, Andrew D. Farmer, Stephanie Widdison, Thierry Barchietto: Anilinopyrimidine Resistance in Botrytis cinerea Is Linked to Mitochondrial Function . In: Frontiers in Microbiology . tape 8 , November 30, 2017, ISSN  1664-302X , doi : 10.3389 / fmicb.2017.02361 , PMID 29250050 , PMC 5714876 (free full text).
10. ↑ Directive 2006/64 / EC of the Commission of July 18, 2006 (PDF) amending Council Directive 91/414 / EEC to include the active substances clopyralid, cyprodinil, fosetyl and trinexapac.
11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on cyprodinil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.
12. ↑ Ordinance of the EDI on the maximum levels for pesticide residues in or on products of plant and animal origin. In: admin.ch . Retrieved February 6, 2020 .