Definition
ChEBI: A member of the class of N-alkylpiperazines in which the two amino groups of piperazine are replaced by 1-formamido-2,2,2-trichloroethyl groups. A fungicide active against a range of diseases including powdery mildew, scab and rust.
General Description
Colorless crystals. Non corrosive. Used as a fungicide.
Reactivity Profile
A piperazine, trichloromethylformamide derivative. Decomposed in strong acid to trichloroacetaldehyde and piperazine salts, and in strongly alkaline media to chloroform and piperazine.
Hazard
Low toxicity by ingestion, inhalation, and
skin contact. Human systemic effects.
Agricultural Uses
Fungicide: Triforine is a systemic fungicide with protectant,
eridicant, and curative activity. It is locally systemic, is
quickly absorbed by the plant and should be applied on or
before an infection occurs. Triforine is used for control of
black spot, brown rot, scab, petal blight, rust and other diseases on fruits such as apples, peaches, plumbs, nectarines,
apricots, and strawberry; in hops, vegetables, cereals, and
ornamentals such as roses and chrysanthemums. Triforine
breaks down rapidly in the environment. Not approved for
use in EU countries
. Registered for use in the U.S.
Trade name
CELA50®; CW524®; DENARIN®
FUNGINEX®; SAPROL®; TRIFORIN®; W524®
Metabolic pathway
Thermal reaction of triforine with several alcohols in a
closed glass tube gives N-(1-alkoxy-2,2,2-
trichloroethyl) formamides.
Degradation
Triforine (1) is stable up to 180°C. It decomposes in aqueous solution
when exposed to daylight or UV light. In strongly acid media, it is
decomposed to trichloroacetaldehyde and piperazine salts. In strongly
basic media, triforine decomposes to give chloroform and piperazine
(DT50 3.5 days at pH 5-7, 25 °C). From an unbuffered aqueous solution
stored for 13 weeks, four hydrolysis products of triforine, 5, 6, 7 and 3,
were isolated by preparative thin-layer chromatography. After 6 months
at room temperature in an unbuffered solution, 7 was the major product.
These products indicate that stepwise removal of substituents from the
nitrogen atoms of the ring occurred and the composition of the mixtures
produced by hydrolysis was shown to be pH- and time-dependent
(Scheme 1).
When solid triforine was irradiated with UV light (254 nm) for 1, 16
or 64 hours, analysis of the products showed that one side chain was
removed preferentially and the second was attacked more slowly.
Products 2, 3, 4 [N-(2,2-dichlorovinyl)formamide], 12 (probably formed
by reaction of 2 with chloral, a photoproduct) and 2,2,2-trichloroethane-
1,1-diol were identified and minor amounts of six other products were
detected by thin-layer chromatography. Compound 2 is probably the
major photolytic product. When triforine was irradiated in solution in
deionised water with a quartz high pressure lamp (maximum energy at
366 nm), 4 was isolated and identified as a product of photolysis but was
itself photolabile and could no longer be detected after 5 hours irradiation
(Darda et al., 1977).
