Pymetrozine

Last updated
Pymetrozine
Pymetrozin.svg
Pymetrozine.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.121.006 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 602-927-1
KEGG
PubChem CID
UNII
  • InChI=1S/C10H11N5O/c1-8-7-15(10(16)14-13-8)12-6-9-3-2-4-11-5-9/h2-6H,7H2,1H3,(H,14,16)/b12-6+
    Key: QHMTXANCGGJZRX-WUXMJOGZSA-N
  • CC1=NNC(=O)N(C1)/N=C/C2=CN=CC=C2
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: [1]
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H332, H351, H361fd, H410, H412
P201, P273, P280, P301, P308+P313
Lethal dose or concentration (LD, LC):
5820 mg/kg, Oral (Rat); >2000 mg/kg, percutaneous (Rat); >2000 mg/kg, oral (Bobwhite quail)
>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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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] It selectively targets the nervous system of sap-feeding insects, causing them to cease feeding soon after ingestion. This unique mechanism limits impact on non-target beneficial insects. Pymetrozine has been extensively used on rice, potato and brassica crops as an alternative to organophosphorus pesticides. [4] [5]

Contents

Mechanism of action

Pymetrozine is a neurotoxic insecticide that selectively affects chordotonal mechanoreceptors present in the legs of sap-feeding insects. [6] It targetes specific ion channels in the nervous system of insects, particularly the transient receptor potential vanilloid (TRPV) channels. [7] [3] It is in IRAC group 9B. [8] These channels, which consist of two key protein subunits, play a crucial role in insect sensory signal transduction. When pymetrozine binds to these channels, it alters their activity, leading to increased sensitivity and disruption of normal neuronal signaling. This results in abnormal 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. It does not interfere with plant growth processes, even after leaf-targeted applications. [5] [9]

Safety

Pymetrozine can cause cancer according to The Environmental Protection Agency (EPA). [10] Pymetrozine is of low acute toxicity to humans, mammals, birds, aquatic organisms, and bees. [6] It is a respiratory tract irritant and ingestion may affect major organs at high doses. It may cause reproductive or developmental defects. [11]

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. [12] Nicotinaldehyde (3-PCA) and 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine are the primary photolysis products of pymetrozine. [13] Exposure to 3-PCA has been reported to cause developmental toxicity in zebrafish. [14]

Use

The annual usage of pymetrozine was at least 4.45 × 103 t in China according to its consumption (150 g/ha) and area of rice field (2.97 × 107 ha). [15]

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. 1 2 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.
  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. 1 2 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.
  6. 1 2 "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. Bibcode:2021PMSci..77.2609S. 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. Bibcode:2022JESHB..57..339W. 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 (Pt B): 127197. Bibcode:2022JHzM..42327197L. doi:10.1016/j.jhazmat.2021.127197. ISSN   0304-3894. PMID   34844343.
  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. Bibcode:2023EcoES.25314654C. 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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