Pymetrozine is an insecticide in the pyridine-azomethine chemical class, primarily utilized for controlling homopteran pests, such as aphids and whiteflies, in agricultural settings[1]. 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.[2][3]
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| Names | |
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| IUPAC name
6-methyl-4-[(E)-pyridin-3-ylmethylideneamino]-2,5-dihydro-1,2,4-triazin-3-one
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| Other names
Pymetrozin, Fulfill, Plenum, Endeavor
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
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| Properties | |
| C10H11N5O | |
| Molar mass | 217.23 g/mol |
| Density | 1.36 g/cm3 |
| Melting point | 217 °C |
| 2.25g/l 20 °C(Ethanol); 290mg/l, 25 °C (Water); <0.001g/l, 20 °C (Hexane) | |
| Hazards | |
| GHS labelling:[4] | |
  
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| Warning | |
| H332, H351, H361fd, H410, H412 | |
| P201, P273, P280, P301, P308+P313 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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5820 mg/kg, Oral (Rat); >2000 mg/kg, percutaneous (Rat); >2000 mg/kg, oral (Bobwhite quail) |
LC50 (median concentration)
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>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).
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Mechanism of action
editPymetrozine is a neuroactive insecticide that selectively affects chordotonal mechanoreceptors.[5] It targetes specific ion channels in the nervous system of insects, particularly the transient receptor potential vanilloid (TRPV) channels[6]. These channels, which consist of two key protein subunits, play a crucial role in sensory signal transduction. When pymetrozine binds to these channels, it alters their activity, leading to increased sensitivity and disruption of normal neuronal signaling. This mechanism results in impaired movement and behavior in target insects. Pymetrozine acts both on the plant’s surface and internally, moving through vascular channels in multiple directions. It penetrates leaf tissues and remains effective when applied to either foliage or soil. Its internal movement within the plant does not interfere with growth processes, even after leaf-based applications.[3][7]
Safety
editPymetrozine can cause cancer according to The Environmental Protection Agency (EPA).[8] Pymetrozine has been determined to be of low acute toxicity to humans, birds, aquatic organisms, mammals, and bees.[5]
See also
editReferences
edit- ^ 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 (inactive 2024-10-31), ISBN 978-3-662-03565-8, retrieved 2024-10-29
{{citation}}: CS1 maint: DOI inactive as of October 2024 (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.
- ^ a b 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. doi:10.1242/jeb.01917. ISSN 1477-9145. PMID 16339866.
- ^ "ECHA Classification for Pymetrozine". European Chemicals Agency. Retrieved 2024-10-29.
- ^ a b "T3DB: Pymetrozine". www.t3db.ca. Retrieved 2024-10-29.
- ^ Wang, Li-Xiang; Niu, Chun-Dong; Salgado, Vincent L.; Lelito, Katherine; Stam, Lynn; Jia, Ya-Long; Zhang, Yan; Gao, Cong-Fen; Wu, Shun-Fan (2019-01-01). "Pymetrozine activates TRPV channels of brown planthopper Nilaparvata lugens". Pesticide Biochemistry and Physiology. 153: 77–86. Bibcode:2019PBioP.153...77W. doi:10.1016/j.pestbp.2018.11.005. ISSN 0048-3575. PMID 30744899.
- ^ 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, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 40–49, doi:10.1007/978-3-662-03565-8_3 (inactive 2024-10-31), ISBN 978-3-642-08314-3, retrieved 2024-10-29
{{citation}}: CS1 maint: DOI inactive as of October 2024 (link) - ^ "California Office of Environmental Health Hazard Assessment (OEHHA)". oehha.ca.gov. Retrieved 2024-10-29.