Myclobutanil

Structural formula
	Structural formula without specifying the stereochemistry (stereocenter is marked with a * )
General
Surname	Myclobutanil
other names	( RS ) -2- (4-chlorophenyl) -2- (1 H -1,2,4-triazol-1-ylmethyl) hexanenitrile ( IUPAC ) ; Deccotanil; eagle; Fungi; nova; Systhane; (±) -2- (4-chlorophenyl) -2- (1 H -1,2,4-triazol-1-ylmethyl) hexanenitrile;
Molecular formula	C 15 H 17 ClN 4
Brief description	pale yellow crystals
External identifiers / databases
EC number	410-400-0
ECHA InfoCard	100,101,000
PubChem	6336
ChemSpider	6096
Wikidata	Q413587
properties
Molar mass	288.77 g · mol -1
Physical state	firmly
density	1.22 g cm −3
Melting point	70-71.5 ° C ; 63-68 ° C;
boiling point	202-208 ° C (133 Pa)
Vapor pressure	0.213 mPa (25 ° C)
solubility	practically insoluble in water (142 mg l −1 at 25 ° C); soluble in most organic solvents;
safety instructions
H and P phrases	H: 302-319-361d-411
	P: 201-264-273-280-308 + 313
Toxicological data	1600 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Myclobutanil is a racemic mixture of two enantiomeric chemical compounds from the group of the triazoles , nitriles and chlorophenyls and a systemic azole fungicide developed by Rohm and Haas in the late 1980s .

Stereoisomerism

Myclobutanil is a 1: 1 mixture ( racemate ) of the ( R ) - and ( S ) -configured enantiomer.

Enantiomers of myclobutanil
Surname	( S ) -Myclobutanil	( R ) -Myclobutanil
other names	(-) - myclobutanil	(+) - myclobutanil
Structural formula
CAS number	244094-39-1	244094-40-4
	88671-89-0 (mixture of isomers)
EC number	410-400-0, 618-198-8 (mixture of isomers)
ECHA info card	100.101.000 , 100.115.883 (mixture of isomers)
PubChem	38989055	11077077
	6336 (mixture of isomers)
Wikidata	Q27157152	Q27157150
	Q413587 (mixture of isomers)

synthesis

In the production of myclobutanil, 4-chlorophenylacetonitrile and 1-chlorobutane first react with one another. A bromomethane group is then added by reaction with dibromomethane . The bromine is substituted with 1,2,4-triazole in the last step .

use

Estimated US application rate in 2011

Myclobutanil is used as a broad-spectrum fungicide in agriculture and in home gardens (especially in ornamental plants, fruit trees and in viticulture against scab , rust and mildew ).

The action is based on inhibition of ergosterol - biosynthesis .

Admission

Myclobutanil is approved as an active ingredient in plant protection products in many EU countries, including Germany and Austria, and Switzerland.

safety instructions

Myclobutanil is only slightly toxic to humans. In animal experiments, damage to embryos was demonstrated at high doses. It is highly toxic to fish, algae and zooplankton .

Individual evidence

↑ ^a ^b ^c Entry on myclobutanil. In: Römpp Online . Georg Thieme Verlag, accessed on May 14, 2014.
↑ ^a ^b ^c ^d ^e Decision Document of the Plant Industry Directorate of Canada ( Memento of October 5, 2006 in the Internet Archive ).
↑ entry to myclobutanil at ChemBlink , accessed on February 25 2011th
↑ Product Sheet .
↑ ^a ^b Entry on myclobutanil in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .
↑ Entry on α-n-butyl-α- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturer or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 714 ( limited preview in Google Book search).
^ Joint Meeting on Pesticide Residues (JMPR), Monograph for Myclobutanil , accessed December 9, 2014.
↑ Directorate-General for Health and Food Safety of the European Commission: Entry on myclobutanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[roempp-1] Entry on myclobutanil. In: Römpp Online . Georg Thieme Verlag, accessed on May 14, 2014.

[pmra-2] Decision Document of the Plant Industry Directorate of Canada ( Memento of October 5, 2006 in the Internet Archive ).

[3] try to myclobutanil at ChemBlink , accessed on February 25 2011th

[4] Product Sheet .

[GESTIS-5] Entry on myclobutanil in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .

[CLP_100.101.000-6] Entry on α-n-butyl-α- (4-chlorophenyl) -1H-1,2,4-triazole-1-propanenitrile in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturer or distributors can expand the harmonized classification and labeling .

[unger-7] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 714 ( limited preview in Google Book search).

[8] Joint Meeting on Pesticide Residues (JMPR), Monograph for Myclobutanil , accessed December 9, 2014.

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on myclobutanil in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.