Nuarimol

Structural formula
	Basic structural formula (stereocenter is marked with an * )
General
Surname	Nuarimol
other names	Trimidal; Tridal; (±) -α- (2-Chlorophenyl) -α- (4-fluorophenyl) -5-pyrimidinemethanol; ( RS ) -2-chloro-4'-fluoro-α- (pyrimidin-5-yl) benzhydryl alcohol;
Molecular formula	C 17 H 12 ClFN 2 O
External identifiers / databases
EC number	264-071-1
ECHA InfoCard	100.058.228
PubChem	91683
Wikidata	Q15632816
properties
Molar mass	314.74 g mol −1
Physical state	firmly
Melting point	126 ° C
solubility	practically insoluble in water (0.026 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-319
	P: 305 + 351 + 338
Toxicological data	1250 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nuarimol is a mixture of two enantiomeric chemical compounds from the group of pyrimidines (more precisely pyrimidine carbinole ). It was introduced by Eli Lilly in 1975 and was approved as a plant protection product in Germany under the trade name Trimidal until 2000 .

Nuarimol is used as a systemic fungicide to control powdery mildew in special crops (wine, pome fruit, stone fruit and hops). Together with Imazalil it was also used for seed dressing in cereal cultivation. Nuarimol works by inhibiting C14 demethylase .

Extraction and presentation

Nuarimol is made by reacting 5-bromopyrimidine with 2-chloro-4'-fluoro-benzophenone (2-chlorophenyl-4-fluorophenyl ketone).

Stereoisomerism

Nuarimol is chiral , there are two enantiomers : ( R ) -2-chloro-4′-fluoro-α- (pyrimidin-5-yl) benzhydryl alcohol [= ( R ) form] and ( S ) -2-chloro-4 ′ -Fluoro-α- (pyrimidin-5-yl) benzhydryl alcohol [= ( S ) -form]. The ( racemic ) ( RS ) -2-chloro-4'-fluoro-α- (pyrimidin-5-yl) benzhydryl alcohol is used as a fungicide, i.e. a 1: 1 mixture of ( R ) and ( S ) configuration .

Nuarimol (2 enantiomers)
( S ) configuration	( R ) configuration

Admission

In 2004 the EU Commission decided not to include Nuarimol in the list of active ingredients permitted for plant protection products. In Switzerland, Austria and Germany no pesticides with the active ingredient Nuarimol are approved.

Individual evidence

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-300.
↑ ^a ^b ^c Entry on Nuarimol in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 27, 2013.
↑ ^a ^b Nuarimol data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 560 ( limited preview in Google Book search).

↑ Commission Decision of 30 January 2004 not to include certain active substances in Annex I to Directive 91/414 / EEC and the withdrawal of authorizations for plant protection products containing these substances (2004/129 / EC) .

↑ General Directorate Health and Food Safety of the European Commission: Entry on Nuarimol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.

[crc-1] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-300.

[ppdb-2] Entry on Nuarimol in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 27, 2013.

[Sigma-3] Nuarimol data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 560 ( limited preview in Google Book search).

[5] Commission Decision of 30 January 2004 not to include certain active substances in Annex I to Directive 91/414 / EEC and the withdrawal of authorizations for plant protection products containing these substances (2004/129 / EC) .

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on Nuarimol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.