IPCS INCHEM Home


    TRIFORINE         JMPR 1977

    IDENTITY

    Chemical name

    1,4-bis(2,2,2-trichloro-1-formamidoethyl)piperazine
    1,1'-piperazine-1,4-diyldi-(N-(2,2,2-trichloroethyl)formamide)

    Synonyms

    Cela W 524, W 524, Saprol(R), Flanginex

    Structural formula

    CHEMICAL STRUCTURE 12


    Other information on identity and properties

    State:              colorless and odorless, crystalline
    Melting point:      155C

    Triforine is hydrolysed rapidly in aqueous solutions at 21C, about
    50% being degraded in the first two clays with the formation of
    chloride ions and, through several intermediates,
    1-(dihydroxyacetyl)piperazine and piperazine. On exposure to sunlight,
    about half of the triforine was degraded in 150 hours.

    Photolysis by ultraviolet light in the absence of water leads
    preferentially to the removal of one side chain, the second side chain
    being attacked more slowly.

    In aqueous solution, triforine is rapidly decomposed by ultraviolet
    light. N-(2,2dichlorovinyl)formamide was isolated as an intermediate
    photodecomposition product (Darda et al., 1977),

    After 3 hours irradiation with u.v. light or 30 hours exposure to
    sunlight, 50% of triforine in aqueous solution was inactivated
    (Buchenanery 1975).

    EVALUATION FOR ACCEPTABLE DAILY INTAKE

    BIOCHEMICAL ASPECTS

    Absorption, metabolism and excretion

    Male Wistar rats, weighing approximately 200 g, were dosed orally with
    2.3 3H)-triforine (ring labelled) or 3.75 mg 14C-triforine (side
    chains labelled.

    After oral administration to 9 animals the blood level curve passed
    its maximum (1.3% of the administered dose) 4 hours after dosage,
    followed by a more rapid decrease in the 4-10 hours interval and a
    subsequent slower fall. At the end of this blood level experiment
    (96 hours), an average of 0.3% of the administered radioactivity was
    present in the total blood compartment of the rat. The main portion of
    the total radioactivity, 74.3% of the (3H)-triforine and 52.5% of the
    (14C)-labelled triforine, was excreted reneally within the first
    24 hours. In this period the faecal excretion amounted to 16.5% of the
    (3H)-labelled and 39.5% of the (14C)-labelled triforine. The average
    total triforine eliminated by the rat within one day of dosing was
    90.8% (3H) and 92.0% (14C).

    During a period of 30 hours after dosing, 19% of the orally
    administered (3H) dose was 15% of the (14C) dose was excreted via
    the bile. The elimination in the urine following increased dose of
    triforine (25, 50, 100 and 200 mg/kg for 8 animals) followed the same
    metabolic pattern: 70% of the (3H)-labelled and 50% of the
    (14C)-labelled substance was excreted after 24 hr. The main
    metabolite in the urine was identified as
    N-(2,2,2-trichloro-1-(piperazin-1-yl)ethyl)formaide (Darda, 1977).

    COMMENTS

    In rats, the compound was rapidly absorbed and excreted, mainly in the
    urine. The main metabolite was
    N-(2,2,2-trichloro-1-(piperazin-1-yl)ethyl)formaide.

    Full toxicological data are required before a recommendation of the
    ADI for humans can be made.

    RESIDUES IN FOOD AND THEIR EVALUATION

    No data were available for consideration.

    FURTHER WORK OR INFORMATION

    REQUIRED by 30 June 1978 and before an acceptable daily intake for
    humans (ADI) can be established and maximum residue limits (MRL) can
    be recommended.

    1.   Submission of full data relating to toxicological and residue
         studies.

    REFERENCES

    Buchanauer, H. (1975) Inactivation of triforine by u.v. and sunlight
    on glass and on leaves of bean plant. Pestic. Sci. 6, 553-559.

    Darda, S. (1977) Absorption, metabolism and excretion of the fungicide
    triforine in the rat. Pestic. Sci. 8, 193-202.

    Darda, S., Darskus, R.L., Eichler, D. Ost, W. and Wotschokowsky, M.
    (1977) Hyrdolysis and photolysis of the fungicide triforine. Pestic.
    Sci 8, 183-192.
    


    See Also:
       Toxicological Abbreviations