| Identification | Back Directory | [Name]
Triflumizole | [CAS]
99387-89-0 | [Synonyms]
Triumizole
Triflumizole
Triflumizole [iso]
fungicide Triflumizole
Triumizole Solution, 1000ppm
N-[4-chloro-2-(trifluoromethyl)phenyl]-1-imidazol-1-yl-2-propoxyethanimine
(E)-1-(1-((4-Chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole
4-Chloro-N-[(E)-1-(1H-imidazol-1-yl)-2-propoxyethylidene]-2-(trifluoromethyl)aniline
(E)-N-[4-Chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-(propyloxy)ethanimine
(E)-4-CHLORO-ALPHA,ALPHA,ALPHA-TRIFLUORO-N-(1-IMIDAZOL-1-YL-2-PROPOXYETHYLIDENE)-O-TOLUIDINE | [Molecular Formula]
C15H15ClF3N3O | [MOL File]
99387-89-0.mol | [Molecular Weight]
345.75 |
| Questions And Answer | Back Directory | [Synthesis]
The reaction of an equimolar mixture of 2-trifluoromethyl-4-chloroaniline and α-propoxyacetic acid in the presence of phosphorus pentachloride produces an amide compound, which undergoes iminochlorination by passing phosgene in the presence of triethylamine, and finally reacts with imidazole to produce Triflumizole. The reaction formula is as follows:
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| Hazard Information | Back Directory | [Uses]
Triflumizole is used for the control of Gymnospurangum and
Venturia spp. in pome fruit, against powdery Erysiphaceae in fruit and
vegetables, and against Fusarium, Fulvia and Monilia spp. It is also
used as a seed treatment against Helminthospurium, Tilletia and Ustilago
spp. in cereals. | [Definition]
ChEBI: Triflumizole is a carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of monochlorobenzenes, a member of imidazoles, a member of (trifluoromethyl)benzenes, a carboxamidine, an ether, a conazole fungicide and an imidazole fungicide. | [Metabolic pathway]
Triflumizole is unstable in aqueous solution when exposed to light and
it is readily metabolised by plants and animals. The primary route
of metabolism is by cleavage of the imidazole ring to give several
metabolites which retain the 4-chloro-2-trifluoromethylaniline moiety.
The major metabolite in crops, 2, is formed by loss of the imidazole
ring. | [Degradation]
Aqueous solutions of triflumizole are degraded by sunlight with a DT50 of
29 hours. The sole hydrolysis product of triflumizole in the dark is 2,
which is formed by loss of the imidazole ring.
The major product of photolysis of triflumizole is 4, which is probably
formed in the presence of oxygen via 3. This compound was soluble in the
solid state but decomposed in solution, even if stored in a refrigerator
(Hashimoto et al., 1990). |
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