Pymetrozine

Structural formula
General
Surname	Pymetrozine
other names	( E ) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2 H ) -one; 6-methyl-4 - [( E ) - (pyridin-3-ylmethylene) amino] -4,5-dihydro-2 H - [1,2,4] -triazin-3-one ( IUPAC );
Molecular formula	C 10 H 11 N 5 O
Brief description	beige solid
External identifiers / databases
EC number	602-927-1
ECHA InfoCard	100.121.006
PubChem	9576037
Wikidata	Q2119621
properties
Molar mass	217.23 g mol −1
Physical state	firmly
density	1.36 g cm −3
Melting point	216 ° C (decomposition)
solubility	very heavy in water (0.29 g l −1 at 25 ° C); soluble in dichloromethane , ethyl acetate and ethanol;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 351-412
	P: 273-281
Toxicological data	5820 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 .

Pymetrozine is an active ingredient for crop protection and a chemical compound from the group of pyridine - azomethines .

Extraction and presentation

Pymetrozine can be obtained by alkylation of 5-trifluoromethyl-1,3,4-oxadiazol-2 (3 H ) -one with chloroacetone, subsequent reaction with hydrazine hydrate and condensation with nicotinaldehyde to form the imine .

Alternatively, it can be obtained by reacting 3-pyridine carbonitrile by forming the corresponding aldehyde and condensing it with 4-amino-6-methyl-4,5-dihydro-1,2,4-triazin-3 (2 H ) -one.

properties

Pymetrozine is a colorless to beige solid that is sparingly soluble in water and, as a technical product, has a slightly sweet odor.

use

Pymetrozine is used as an active ingredient in crop protection products. It is used as a selective insecticide against constant winged animals and replaces organophosphates . The exact biochemical mode of action in insects is not known, but it has effects on neuroregulation or nerve-muscle interaction. Physiologically, it seems to prevent the insects from stinging the plant tissue. It was first synthesized in 1986, patented by Ciba-Geigy in 1989, and marketed by Syngenta .

Admission

Pymetrozine was approved in the EU as an insecticide for fruit, vegetables, potatoes, oilseeds, hops, tobacco and ornamental plants since 2001.

The routine extension of approval in the EU was rejected by the European Commission in October 2018 due to toxic breakdown products in water and plants as well as endocrine effects , so that use as a plant protection product in the EU is no longer permitted from January 31, 2020.

In Switzerland, plant protection products (e.g. Chess, Plenum) with this active ingredient are permitted.

safety instructions

According to the CLP regulation, pymetrozine is classified in the group of substances that can presumably cause cancer.

Web links

Assessment of the ecological sustainability of pymetrozine in comparison with the reference product Sukmeron (PDF; 123 kB)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 123312-89-0 in the GESTIS substance database of the IFA , accessed on July 4, 2012(JavaScript required) .
↑ ^a ^b ^c ^d EPA: Pesticide Fact Sheet of Pymetrozine for Conditional Registration , August 2000.
↑ ^a ^b EU: Review report for the active substance pymetrozine - Finalized in the Standing Committee on Plant Health at its meeting on 29 June 2001 in view of the inclusion of pymetrozine in Annex I of Directive 91/414 / EEC. (PDF; 95 kB)
↑ Entry on (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one 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 .
↑ ^a ^b data sheet pymetrozine, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 674 ( limited preview in Google Book search).
↑ ^a ^b Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 1327 ( limited preview in Google Book search).
↑ Implementing Regulation (EU) 2018/1501 of the Commission of 9 October 2018 on the non-renewal of the approval for the active substance pymetrozine in accordance with Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the implementing regulation (EU) No. 540/2011 of the Commission . 32018R1501, October 10, 2018 ( europa.eu [accessed October 25, 2018]).
↑ General Directorate Health and Food Safety of the European Commission: Entry on pymetrozine in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 123312-89-0 in the GESTIS substance database of the IFA , accessed on July 4, 2012(JavaScript required) .

[EPA-2] EPA: Pesticide Fact Sheet of Pymetrozine for Conditional Registration , August 2000.

[EU-3] EU: Review report for the active substance pymetrozine - Finalized in the Standing Committee on Plant Health at its meeting on 29 June 2001 in view of the inclusion of pymetrozine in Annex I of Directive 91/414 / EEC. (PDF; 95 kB)

[CLP_100.121.006-4] Entry on (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one 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 .

[Sigma-5] ta sheet pymetrozine, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[Unger-6] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 674 ( limited preview in Google Book search).

[Wolfgang_Krämer,_Ulrich_Schirmer-7] Wolfgang Krämer, Ulrich Schirmer: Modern Crop Protection Compounds . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 1327 ( limited preview in Google Book search).

[8] Implementing Regulation (EU) 2018/1501 of the Commission of 9 October 2018 on the non-renewal of the approval for the active substance pymetrozine in accordance with Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the implementing regulation (EU) No. 540/2011 of the Commission . 32018R1501, October 10, 2018 ( europa.eu [accessed October 25, 2018]).

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on pymetrozine in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.