Hydramethylnon

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]

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
CAS Number	67485-29-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:38531 Y
ChEMBL	ChEMBL464812 Y
ChemSpider	4445168 Y
ECHA InfoCard	100.100.669
KEGG	C10994 Y
PubChem CID	5281875
UNII	J265GZ7MFJ Y
CompTox Dashboard (EPA)	DTXSID6023868
InChI 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+ Y Key: IQVNEKKDSLOHHK-FNCQTZNRSA-N Y 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
SMILES FC(F)(F)c1ccc(cc1)C=CC(=NNC2=NCC(C)(C)CN2)C=Cc3ccc(cc3)C(F)(F)F
Properties
Chemical formula	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)	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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