Hydramethylnon

Hydramethylnon
Names
IUPAC name
2(1H-4,4-dimethyl tetrahydro pyrimidinylidene )

(3-(4-(trifluoromethyl)phenyl) -1-(2-(4-(trifluoromethyl)phenyl)ethenyl)

-2-propenylidene)hydrazone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.100.669 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+ checkY
    Key: IQVNEKKDSLOHHK-FNCQTZNRSA-N checkY
  • InChI=1/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+
    Key: IQVNEKKDSLOHHK-FNCQTZNRBM
  • FC(F)(F)c1ccc(cc1)C=CC(=NNC2=NCC(C)(C)CN2)C=Cc3ccc(cc3)C(F)(F)F
Properties
C25H24F6N4
Molar mass 494.485 g·mol−1
Appearance Yellow to orange crystalline solid
Melting point 185 to 190 °C (365 to 374 °F; 458 to 463 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Hydramethylnon (AC 217,300) is an insecticide used primarily in the form of baits for cockroaches and ants.[1][2][3] It works by inhibiting complex III in the mitochondrial inner membrane and leads to a halting of oxidative phosphorylation (IRAC class 20A). Some brands of hydramethylnon are Amdro, Blatex, Combat, Cyaforce, Cyclon, Faslane, Grant's, Impact, Matox, Maxforce, Pyramdron, Siege, Scuttle and Wipeout. Hydramethylnon is a slow-acting poison with delayed toxicity that needs to be eaten to be effective.[4]

Toxicology

Hydramethylnon has low toxicity in mammals.[2][4] The oral LD50 is 1100–1300 mg/kg in rats and above 28,000 mg/kg in dogs.[4] Hydramethylnon is toxic to fish; the 96-hour LC50 in rainbow trout is 0.16 mg/L, 0.10 mg/L in channel catfish, and 1.70 mg/L in bluegill sunfish.

Hydramethylnon, when fed to rats for two years, led to an increase in uterine and adrenal tumors at the highest dose; therefore, the Environmental Protection Agency classifies hydramethylnon as a possible human carcinogen.[4]

See also

  • Fipronil, another insecticide used for similar purposes

References

  1. ^ Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "32.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1156–1201. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)
  2. ^ a b Veterinary Support Personnel Network
  3. ^ "Hydramethylnon". PubChem.
  4. ^ a b c d "Hydramethylnon" (PDF). National Pesticide Information Center.

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