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Pymetrozine

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Pymetrozine
Names
IUPAC name 6-methyl-4--2,5-dihydro-1,2,4-triazin-3-one
Other names Pymetrozin, Fulfill, Plenum, Endeavor
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.121.006 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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/cm
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 GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pymetrozine is an insecticide in the pyridine-azomethine chemical class, primarily utilized for controlling homopteran pests, such as aphids and whiteflies, in agricultural settings. 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.

Mechanism of action

Pymetrozine is a neuroactive insecticide that selectively affects chordotonal mechanoreceptors present in the legs of sap-feeding insects. It targetes specific ion channels in the nervous system of insects, particularly the transient receptor potential vanilloid (TRPV) channels. It is in IRAC group 9B. 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.

Safety

Pymetrozine can cause cancer according to The Environmental Protection Agency (EPA). Pymetrozine is of low acute toxicity to humans, mammals, birds, aquatic organisms, and bees. It is a respiratory tract irritant and ingestion may affect major organs at high doses. It may cause reproductive or developmental defects.

Ecotoxicity

Pymetrozine has low off-target effects.

The half-life of pymetrozine in water, soil, and rice plants is 2.81, 6.95, and 3.70 days respectively. 3-pyridinecarboxaldehyde (3-PCA) and 4-amino-6-methyl-2 H-1,2,4-triazine-3-one are the primary degradation products of pymetrozine on photodegradation. Exposure to 3-PCA has been reported to cause developmental toxicity in zebrafish.

Use

The annual usage of pymetrozine was at least 4.45 × 10 t in China according to its consumption (150 g/ha) and area of rice field (2.97 × 107 ha).

References

  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
  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. 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.
  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. doi:10.1242/jeb.01917. ISSN 1477-9145. PMID 16339866.
  6. ^ "T3DB: Pymetrozine". www.t3db.ca. Retrieved 2024-10-29.
  7. 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.
  8. Sparks, Thomas C; Storer, Nicholas; Porter, Alan; Slater, Russell; Nauen, Ralf (2021). "Insecticide resistance management and industry: the origins and evolution of the I nsecticide R esistance A ction C ommittee (IRAC) and the mode of action classification scheme". Pest Management Science. 77 (6): 2609–2619. doi:10.1002/ps.6254. ISSN 1526-498X. PMC 8248193. PMID 33421293.
  9. 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, ISBN 978-3-642-08314-3, retrieved 2024-10-29
  10. "California Office of Environmental Health Hazard Assessment (OEHHA)". oehha.ca.gov. Retrieved 2024-10-29.
  11. Hertfordshire, University of. "Pymetrozine (Ref: CGA 215944)". sitem.herts.ac.uk. Retrieved 2024-11-07.
  12. Wei, Haifeng; Chen, Guiquan; Yang, Xiaoyun (2022-05-04). "Residues and degradation dynamics of pymetrozine and chlorpyrifos in rice field ecosystem". Journal of Environmental Science and Health, Part B. 57 (5): 339–349. doi:10.1080/03601234.2022.2056393. ISSN 0360-1234. PMID 35362360.
  13. Liang, Ximei; Guan, Fangling; Ling, Zhiyou; Wang, Honghong; Tao, Yunwen; Kraka, Elfi; Huang, Huajun; Yu, Chenglong; Li, Danping; He, Jinbao; Fang, Hansun (2022-02-05). "Pivotal role of water molecules in the photodegradation of pymetrozine: New insights for developing green pesticides". Journal of Hazardous Materials. 423: 127197. doi:10.1016/j.jhazmat.2021.127197. ISSN 0304-3894.
  14. Cho, Yerin; Jeon, Hwang-Ju; Kim, Kyeongnam; Kim, Chaeeun; Lee, Sung-Eun (2023-03-15). "Developmental toxicity of a pymetrozine photo-metabolite, 3-pyridinecarboxaldehyde, in zebrafish (Danio rerio) embryos: Abnormal cardiac development and occurrence of heart dysfunction via differential expression of heart formation-related genes". Ecotoxicology and Environmental Safety. 253: 114654. doi:10.1016/j.ecoenv.2023.114654. ISSN 0147-6513. PMID 36801540.
  15. (National Bureau of Statistics of China, 2020, Preetha et al., 2010)
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