Fludioxonil

Structural formula
General
Surname	Fludioxonil
other names	4- (2,2-Difluoro-benzo [1,3] dioxol-4-yl) pyrrole-3-carbonitrile ( IUPAC ); 4- (2,2-Difluoro-1,3-benzodioxol-4-yl) -1 H -pyrrole-3-carbonitrile; CGA173506;
Molecular formula	C 12 H 6 F 2 N 2 O 2
Brief description	odorless, pale yellowish solid
External identifiers / databases
EC number	603-476-3
ECHA InfoCard	100.125.684
PubChem	86398
Wikidata	Q975876
properties
Molar mass	248.19 g mol −1
Physical state	firmly
density	1.54 g cm −3
Melting point	199.8 ° C
boiling point	306 ° C (decomposition)
solubility	almost insoluble in water (1.8 mg l −1 at 25 ° C); soluble in acetone and ethyl acetate ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fludioxonil is a chemical compound from the group of the pyrroles , more precisely the phenylpyrroles, which is derived from pyrrolnitrine .

history

Fludioxonil, together with fenpiclonil, is based on pyrrole nitrine, a secondary metabolite of the bacterium Pseudomonas pyrrocinia .

Extraction and presentation

Fludioxonil can be obtained by a multistage reaction beginning with the regioselective lithiation of 2,2-difluorobenzodioxole and via intermediate steps the conversion of the intermediate product with TosMIC . The synthesis starting with the reaction of 4-amino-2,2-difluorobenzodioxole with acrylonitrile , triethylamine and toluenesulfonylmethyl isocyanate is also possible .

properties

Fludioxonil is an odorless, pale yellowish powder, as a technical product olive green powder, which is practically insoluble in water. It is stable to hydrolysis at pH values of 5, 7 and 9.

use

Fludioxonil is used as a non-systemic fungicide . The effect is based on the inhibition of MAP kinase , which is required for signal transmission for osmoregulation during glycerol synthesis. Fludioxonil is used to treat leaves and seeds in order to combat diseases caused by fungi in the Ascomycetes , Basidiomycetes and Fungi imperfecti departments . It was brought onto the market by Ciba-Geigy in 1993 and was first approved in the USA in 1995.

Admission

In 2007, the EU Commission decided to include fludioxonil in the list of approved active ingredients for plant protection products. In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. Celest) containing this active ingredient are approved. In Switzerland, pineapples have a relatively high maximum residue level of 7 milligrams of fludioxonil per kilogram.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g FAO: FLUDIOXONIL
↑ ^a ^b ^c data sheet Fludioxonil, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Melanie Kettering: Fungal metabolites as chemical messengers and inhibitors of infection-relevant morphogenesis in phytopathogens (diss.) . Tenea, 2005, ISBN 978-3-86504-118-0 , pp. 5 ( limited preview in Google Book search).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 723 ( limited preview in Google Book search).
↑ Viacheslav A. Petrov: Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications . John Wiley & Sons, 2009, ISBN 0-470-52894-X , pp. 411 ( limited preview in Google Book search).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 578 ( limited preview in Google Book search).
↑ Reasoned opinion on the modification of the existing MRLs for fludioxonil in cucurbits inedible peel and radishes . In: EFSA Journal . tape 11 , no. 2 , 2013, p. 3113 , doi : 10.2903 / j.efsa.2013.3113 .
^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49068-X , p. 496 ( limited preview in Google Book search).
↑ Fludioxonil Summary Document. (PDF; 4.9 MB) EPO , June 2011, accessed on July 14, 2017 .
↑ Directive 2007/76 / EC of the Commission of December 20, 2007 (PDF) amending Council Directive 91/414 / EEC to include the active substances fludioxonil, clomazone and prosulfocarb.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Fludioxonil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.
↑ 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 7, 2020 .

[FAO-1] ↑ ^a ^b ^c ^d ^e ^f ^g FAO: FLUDIOXONIL

[Sigma-2] ta sheet Fludioxonil, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[3] Melanie Kettering: Fungal metabolites as chemical messengers and inhibitors of infection-relevant morphogenesis in phytopathogens (diss.) . Tenea, 2005, ISBN 978-3-86504-118-0 , pp. 5 ( limited preview in Google Book search).

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-4] Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 723 ( limited preview in Google Book search).

[Viacheslav_A._Petrov-5] Viacheslav A. Petrov: Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications . John Wiley & Sons, 2009, ISBN 0-470-52894-X , pp. 411 ( limited preview in Google Book search).

[Thomas_A._Unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 578 ( limited preview in Google Book search).

[EFSA-7] Reasoned opinion on the modification of the existing MRLs for fludioxonil in cucurbits inedible peel and radishes . In: EFSA Journal . tape 11 , no. 2 , 2013, p. 3113 , doi : 10.2903 / j.efsa.2013.3113 .

[Horst_Börner,_Klaus_Schlüter-8] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49068-X , p. 496 ( limited preview in Google Book search).

[EPA-9] Fludioxonil Summary Document. (PDF; 4.9 MB) EPO , June 2011, accessed on July 14, 2017 .

[10] Directive 2007/76 / EC of the Commission of December 20, 2007 (PDF) amending Council Directive 91/414 / EEC to include the active substances fludioxonil, clomazone and prosulfocarb.

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Fludioxonil 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 7, 2020 .