TRIFORINE

Description

Triforine is a clear light yellow colour with an ethanol (alcohol) odour and a highly flammable liquid. It is used as a fungicide for the control of black spot, powdery mildew, and diseases of rust in roses, fruits, vegetables, cereals, and ornamentals. Application of triforine acts both as a preventative and a curative fungicide and is known to destroying diseases already in the plant and also preventing disease infestations. It is also used as a post-harvest control of brown rot on peaches, nectarines, apricots, cherries, and plums.

The Uses of TRIFORINE

Triforine is used to control powdery mildews on cereals, fruits, vines, hops, ornamentals, cucurbits and some vegetables, rusts on cereals, fruit, ornamentals and beans. It also controls Munilia spp. on stone fruit, Ascochyta blight on chrysanthemums, black spot on roses, scab on apples and fairy rings on turf. Triforine also suppresses tetranychid mite activity.

The Uses of TRIFORINE

food additive; fungicide; agricultural chemical.

The Uses of TRIFORINE

This pesticide is widely used in flower growing. Cross reactions are expected to diehlorvos.

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®

Contact allergens

This pesticide is widely used in flower growing. Cross- reactions are expected to dichlorvos.

Safety Profile

Low toxicity by ingestion, inhalation, and skin contact. Human systemic effects: change in taste function. When heated to decomposition emits toxic fumes of NOx and Cl-.

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).