Hydramethylnon

Structural formula
General
Surname	Hydramethylnon
other names	1,5-bis [4- (trifluoromethyl) phenyl] -1,4-pentadien-3-one 2- (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl) hydrazone
Molecular formula	C 25 H 24 F 6 N 4
Brief description	odorless, yellow to yellow-brown solid
External identifiers / databases
EC number	405-090-9
ECHA InfoCard	100.100.669
PubChem	5281875
Wikidata	Q413481
properties
Molar mass	494.48 g mol −1
Physical state	firmly
density	1.23 g cm −3
Melting point	187.5 ° C
Vapor pressure	<0.00001 hPa (25 ° C)
solubility	practically insoluble in water (0.01 mg l −1 at 25 ° C); Easily soluble in alcohols; soluble in acetone, chlorobenzene and 1,2-dichloroethane;
safety instructions
H and P phrases	H: 302-319-372-410
	P: 273-301 + 312 + 330-305 + 351 + 338-314
Toxicological data	817 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 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 .

Hydramethylnon is an active ingredient for crop protection and a chemical compound from the group of trifluoromethylaminohydrazones .

Extraction and presentation

Hydramethylnon can be obtained by a condensation reaction of 4-trifluoromethylbenzaldehyde with acetone and the further reaction of the intermediate product formed with a hydrazine derivative .

properties

As a technical product, hydramethylnon is a yellow to yellow-brown crystalline solid with a characteristic odor of vegetable oil. When exposed to light, it is rapidly broken down by photolysis .

use

Hydramethylnon is used as an insecticide . It was originally developed by American Cyanamid in 1977 and is commercially available under the names Amdro, Combat, Faslan, Maxforce, Sensible and Siege, for example. These products are slow-acting poisons that are mainly used against ants on grassy areas, pastureland, ornamental and sports lawns and similar non-agricultural areas. In the USA, hydramethylnon is also used in households and in commercial operations (outside the food industry) against species of ants, silverfish , termites and cockroaches . The action of hydramethylnon is based on the inhibition of the production of ATP in the mitochondria .

Admission

In the EU countries including Germany and Austria as well as in Switzerland no pesticides with the active ingredient hydramethylnon are permitted.

Individual evidence

↑ extoxnet: hydramethylnon
↑ ^a ^b ^c ^d ^e ^f Datasheet Hydramethylnon at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ ^a ^b ^c ^d EPA: Reregistration Eligibility Decision (RED) Hydramethylnon (PDF file; 426 kB).
↑ ^a ^b Entry on 5,5-dimethyl-perhydro-pyrimidin-2-one-alpha- (4-trifluoro-methylstyryl) -alpha- (4-trifluoromethyl) cinnamylidene hydrazone in the GESTIS substance database of the IFA , accessed on January 8th 2020(JavaScript required) .
↑ Entry on 5,5-dimethyl-perhydro-pyrimidin-2-one-α- (4-trifluoromethylstyryl) -α- (4-trifluoromethyl) cinnamylidenehydrazone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Bruce E. Smart, JC Tatlow: Organofluorine chemistry: principles and commercial applications . Springer US, 1994, ISBN 978-0-306-44610-8 ( page 250 in the Google book search).
↑ Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 1098 in the Google book search).
^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 760 in the Google book search).
↑ Mode of action of the most important biocides, part 1 (PDF file; 996 kB).
↑ General Directorate Health and Food Safety of the European Commission: Entry on hydramethylnon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[1] xtoxnet: hydramethylnon

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f Datasheet Hydramethylnon at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[epa-3] EPA: Reregistration Eligibility Decision (RED) Hydramethylnon (PDF file; 426 kB).

[GESTIS-4] Entry on 5,5-dimethyl-perhydro-pyrimidin-2-one-alpha- (4-trifluoro-methylstyryl) -alpha- (4-trifluoromethyl) cinnamylidene hydrazone in the GESTIS substance database of the IFA , accessed on January 8th 2020(JavaScript required) .

[CLP_100.100.669-5] Entry on 5,5-dimethyl-perhydro-pyrimidin-2-one-α- (4-trifluoromethylstyryl) -α- (4-trifluoromethyl) cinnamylidenehydrazone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[Organofluorine-6] Bruce E. Smart, JC Tatlow: Organofluorine chemistry: principles and commercial applications . Springer US, 1994, ISBN 978-0-306-44610-8 ( page 250 in the Google book search).

[modern-7] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 ( page 1098 in the Google book search).

[Roberts-8] Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 760 in the Google book search).

[9] Mode of action of the most important biocides, part 1 (PDF file; 996 kB).

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on hydramethylnon in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.