Pymetrozine

Pymetrozine
Names
	IUPAC name 6-methyl-4-[(E)-pyridin-3-ylmethylideneamino]-2,5-dihydro-1,2,4-triazin-3-one
	Other names Pymetrozin, Fulfill, Plenum, Endeavor
Identifiers
CAS Number	123312-89-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39311;
ChEMBL	ChEMBL1906026;
ChemSpider	7850487;
ECHA InfoCard	100.121.006
KEGG	C18590;
PubChem CID	9576037;
UNII	F0G3V7874J;
CompTox Dashboard (EPA)	DTXSID2032637 ;
	SMILES CC1=NNC(=O)N(C1)/N=C/C2=CN=CC=C2;
Properties
Chemical formula	C10H11N5O
Molar mass	217.23 g/mol
Density	1.36 g/cm3
Melting point	217 °C
Solubility in water	2.25g/l 20 °C(Ethanol); 290mg/l, 25 °C (Water); <0.001g/l, 20 °C (Hexane)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H332, H351, H361fd, H410, H412
Precautionary statements	P201, P273, P280, P301, P308+P313
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	5820 mg/kg, Oral (Rat); >2000 mg/kg, percutaneous (Rat); >2000 mg/kg, oral (Bobwhite quail)
LC50 (median concentration)	>100 mg/l, (96 hr) (Rainbow trout); >5200 ppm, (8 day) (Bobwhite quail)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pymetrozine is an insecticide in the pyridine-azomethine chemical class, primarily utilized for controlling homopteran pests, such as aphids and whiteflies, in agricultural settings.^[2]^[3] Its mode of action selectively targets the feeding behavior of sap-feeding insects, causing them to cease feeding soon after ingestion. This unique mechanism limits its impact on non-target organisms, including beneficial insects. Pymetrozine has been extensively used on rice, potatoes, a wide variety of vegetable brassica crops and various other crops as an alternative to organophosphorus pesticides.^[4]^[5]

^ "ECHA Classification for Pymetrozine". European Chemicals Agency. Retrieved 2024-10-29.
^ Fuog, D.; Fergusson, S. J.; Flückiger, C. (1998), Ishaaya, Isaac; Degheele, Danny (eds.), "Pymetrozine: A Novel Insecticide Affecting Aphids and Whiteflies", Insecticides with Novel Modes of Action: Mechanisms and Application, Berlin, Heidelberg: Springer, pp. 40–49, doi:10.1007/978-3-662-03565-8_3, ISBN 978-3-662-03565-8, retrieved 2024-10-29
^ Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.6 Selective Feeding Blockers: Pymetrozine, Flonicamid, and Pyrifluquinazon". Modern Crop Protection Compounds (3rd ed.). Wiley-VCH. pp. 1501–1526. doi:10.1002/9783527699261. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)
^ Li, Cun; Yang, Ting; Huangfu, Weiguo; Wu, Yinliang (2011-02-01). "Residues and dynamics of pymetrozine in rice field ecosystem". Chemosphere. 82 (6): 901–904. Bibcode:2011Chmsp..82..901L. doi:10.1016/j.chemosphere.2010.10.053. ISSN 0045-6535. PMID 21074245.
^ Ausborn, Jessica; Wolf, Harald; Mader, Wolfgang; Kayser, Hartmut (2005-12-01). "The insecticide pymetrozine selectively affects chordotonal mechanoreceptors". Journal of Experimental Biology. 208 (23): 4451–4466. Bibcode:2005JExpB.208.4451A. doi:10.1242/jeb.01917. ISSN 1477-9145. PMID 16339866.

[1] "ECHA Classification for Pymetrozine". European Chemicals Agency. Retrieved 2024-10-29.

[2] Fuog, D.; Fergusson, S. J.; Flückiger, C. (1998), Ishaaya, Isaac; Degheele, Danny (eds.), "Pymetrozine: A Novel Insecticide Affecting Aphids and Whiteflies", Insecticides with Novel Modes of Action: Mechanisms and Application, Berlin, Heidelberg: Springer, pp. 40–49, doi:10.1007/978-3-662-03565-8_3, ISBN 978-3-662-03565-8, retrieved 2024-10-29

[:0-3] Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.6 Selective Feeding Blockers: Pymetrozine, Flonicamid, and Pyrifluquinazon". Modern Crop Protection Compounds (3rd ed.). Wiley-VCH. pp. 1501–1526. doi:10.1002/9783527699261. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)

[4] Li, Cun; Yang, Ting; Huangfu, Weiguo; Wu, Yinliang (2011-02-01). "Residues and dynamics of pymetrozine in rice field ecosystem". Chemosphere. 82 (6): 901–904. Bibcode:2011Chmsp..82..901L. doi:10.1016/j.chemosphere.2010.10.053. ISSN 0045-6535. PMID 21074245.

[jeb1-5] Ausborn, Jessica; Wolf, Harald; Mader, Wolfgang; Kayser, Hartmut (2005-12-01). "The insecticide pymetrozine selectively affects chordotonal mechanoreceptors". Journal of Experimental Biology. 208 (23): 4451–4466. Bibcode:2005JExpB.208.4451A. doi:10.1242/jeb.01917. ISSN 1477-9145. PMID 16339866.

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