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formetanate hydrochloride
Editor	I.G. Ferris
Entity code	FOHYD
CAS registry No.	23422-53-9
Family	Formamidines
Functions	Acaricide, Insecticide
Chemical name	3-[(EZ)-dimethylaminomethyleneamino]phenyl methylcarbamate hydrochloride (IUPAC) (EN); N,N-dimethyl-N′-[3-[[(methylamino)carbonyl]oxy]phenyl]methanimidamide monohydrochloride (CAS) (EN)
Synonyms	3-dimethylaminomethyleneiminophenyl methylcarbamate hydrochloride
Trade names	Dicarzol (Schering); SN 36056 (Schering); Carzol (NOR-AM)
Other names
Last updated	4/2/2009

Fate
Hydrolysis and oxidative demethylation occurs in soil with a DT50 of 1 to 9 days.

Toxicology
Mammals: Formetanate hydrochloride is rapidly and extensively absorbed after oral administration. It is mainly excreted in urine. No tendency for bioaccumulation. Metabolism of formetanate hydrochloride in animals involves hydrolysis and oxidative demethylation.
It is highly toxic after oral administration and by inhalation. Acute oral LD50 for rats 21, mice 18, dogs 19 mg/kg. Formetanate hydrochloride is not toxic by dermal exposure. Acute percutaneous LD50 for rats >5600, rabbits >10,200 mg/kg. It is considered a skin sensitizer and irritating to eyes.
In 2-year feeding trials, rats and dogs receiving 200 mg/kg diet showed no significant ill-effects.

Detection

Sampling

Methods

MRLs

Uses
Control of spider mites (motile stages) and some insects (including thrips, leaf miners, leafhoppers, flea beetles, lygus bugs, etc.) on ornamentals, pomefruit, stone fruit, citrus fruit, vines, beet, and lucerne.

Notes
Formetanate hydrochloride is a derivative of formetanate [22259-30-9].

Bibliography
EFSA Scientific Report (2006) 69, 1-78, Conclusion on the peer review of formetanate (http://www.efsa.europa.eu:80/cs/BlobServer/PRAPER_Conclusion/praper_concl_sr69_formetanate_efsa_conclusion_final1,0.pdf).

Mode of action
Acaricide and insecticide with contact and stomach action and inhibits the enzyme acetylcholinesterase.

Ecotoxicology
Birds: Acute oral LD50 for chickens 21.5 mg/kg. Ten-day dietary LC50 for bobwhite quail >4640, mallard ducks 6810 mg/kg diet.
Fish: LC50 (96 hours) for rainbow trout 2.8, bluegill sunfish 20 mg/l.
Bees: Toxic to bees.

Plant metabolism & residues
The metabolism of formetanate in plants proceeds by hydrolysis and oxidative demethylation. The parent compound has been identified as the major constituent of the residue on various crops and for various pre-harvest intervals. The identified metabolites are less toxic than the parent compound. Thus the residue definition can be restricted to parent compound only, for both risk assessment and monitoring.
Processing at temperatures of 100°C or higher degrades formetanate to a less toxic compound, 3-hydroxyformanilide. The processed commodities obtained after boiling or sterilization have a significantly lower concentration of formetanate than raw tomatoes.

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