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| | TRIFORINE Basic information |
| Product Name: | TRIFORINE | | Synonyms: | SAPROL;SAPROL(R);N,N'-[PIPERAZINE-1,4-DIYLBIS(TRICHLOROMETHYL)METHYLENE]-DIFORMAMIDE;PIPERAZIN-1,4-DIYL-BIS-[1-(2,2,2-TRICHLOROETHYL)FORMAMIDE];TRIFORIN;TRIFORINE;1,4-bis(1-formamido-2,2,2-trichloroethyl)-piperazin;1,4-bis(1-formamido-2,2,2-trichloroethyl)piperazine | | CAS: | 26644-46-2 | | MF: | C10H14Cl6N4O2 | | MW: | 434.96 | | EINECS: | 247-872-0 | | Product Categories: | Amide structureAlphabetic;Fungicides;Pesticides;TP - TZ;Alpha sort;Amide structurePesticides&Metabolites;Q-ZAlphabetic | | Mol File: | 26644-46-2.mol |  |
| | TRIFORINE Chemical Properties |
| Melting point | 155℃ (decomposition) | | Boiling point | 561.5±50.0 °C(Predicted) | | density | 1.5269 (rough estimate) | | vapor pressure | 8 x 10-2 Pa (25 °C) | | refractive index | 1.6000 (estimate) | | storage temp. | 0-6°C | | solubility | DMSO (Slightly) | | pka | 10.6 (base) | | Water Solubility | 9 mg l-1 (20 °C) | | form | Solid | | color | White to Off-White | | Merck | 13,9762 | | BRN | 626358 | | Henry's Law Constant | 2.6×103 mol/(m3Pa) at 25℃, HSDB (2015) | | Major Application | agriculture
environmental | | InChI | 1S/C10H14Cl6N4O2/c11-9(12,13)7(17-5-21)19-1-2-20(4-3-19)8(18-6-22)10(14,15)16/h5-8H,1-4H2,(H,17,21)(H,18,22) | | InChIKey | RROQIUMZODEXOR-UHFFFAOYSA-N | | SMILES | ClC(Cl)(Cl)C(NC=O)N1CCN(CC1)C(NC=O)C(Cl)(Cl)Cl | | CAS DataBase Reference | 26644-46-2 | | EPA Substance Registry System | Triforine (26644-46-2) |
| Hazard Codes | Xn | | Risk Statements | 52/53-20 | | Safety Statements | 61 | | RIDADR | UN3077 (solid); UN3082
(liquid) | | WGK Germany | 2 | | RTECS | TK9200000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Inhalation
Aquatic Chronic 2 | | Hazardous Substances Data | 26644-46-2(Hazardous Substances Data) | | Toxicity | LD50 oral in rat: 6gm/kg |
| | TRIFORINE Usage And Synthesis |
| 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. | | Chemical Properties | Pure product is white crystal, m.p. 155℃, vapor pressure 2.67×10-8Pa (25℃). Solubility at room temperature: 28.3g/L in dimethylformamide, 1.13g/L in methanol, 1.66g/L in dioxane, 0.88g/L in toluene, slightly soluble in acetone, benzene, carbon tetrachloride, chloroform, dichloromethane, insoluble in dimethylsulfoxide, solubility in water is 27～29mg/L. | | Uses | This pesticide is widely used in flower growing. Cross
reactions are expected to diehlorvos. | | Uses | 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. | | Uses | food additive; fungicide; agricultural chemical. | | 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. | | Production Methods | The commercial production of triforine involves a multi-step synthesis beginning with the formation of two key intermediates: trichloromethyl-substituted aldehydes and piperazine derivatives. These intermediates are then coupled through formylation reactions, where formamide groups are introduced to link the piperazine ring with the trichloromethyl moieties. The process typically uses controlled conditions to ensure the correct substitution pattern and minimize unwanted byproducts. After the coupling step, the crude product undergoes purification, often via crystallisation or solvent extraction, to yield technical-grade triforine—a mixture of isomers used in fungicidal formulations. | | 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. | | Mechanism of action | Systemic with protectant, eradicant and curative characteristics | | 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). | | Pesticide Type | Fungicide |
| | TRIFORINE Preparation Products And Raw materials |
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