| Identification | Back Directory | [Name]
Triadimefon | [CAS]
43121-43-3 | [Synonyms]
ROFON
NUREX
OTRIA
TYPHON
MILTEK
DAYTON
ACIZOL
Amiral
HALETON
meb6447
Tidifon
Azocene
SAMETON
Webeton
bay6681f
MEB 6447
BAYLETON
AMIRAL(R)
FENXIUNIN
diametomb
bayletone
BAY 6681F
Bayleton 5
Bayer 6588
bayletonbm
bayletoncf
Tridimefon
riadimefon
Tridemifone
BAYLETON(R)
TRIADIMEFON
TRIADIMEPHON
BAY MEB 6447
Triadimefone
bayletonbmgel
bayletontotal
Tripinacloraz
Triadimefon 0
bayletontriple
Bayleton 250 EC
Bayleton special
Triadimefon E.C.
Triadimefon W.P.
Monterey bayleton
Triadimefon, >=96%
TriadiMefon Standard
triadimefon solution
Triadimefon in n-Hexane
TRIADIMEFON, 500MG, NEAT
TRIADIMEFON, 250MG, NEAT
Triadimefon solution,100ppm
TRIADIMEFON PESTANAL, 250 MG
triadimefon (bsi,iso)bayleton
Triadimefon Solution, 1000ppm
Triadimefon@100 μg/mL in MeOH
Triadimefon Reference Material
TriadimefonSolution,100mg/L,1ml
TriadimenolSolution,100mg/L,1ml
Triadimefon@1000 μg/mL in Acetone
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL).
4-triazole,1-((tert-butylcarbonyl-4-chlorophenoxy)methyl)-1h-2
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1,2,4-TRIAZOL-1-YL-2-BUTANONE
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1,2,4-TRIAZOL-1-YL)BUTANONE
1-(tert-Butylcarbonyl-(4-chlorophenoxy)methyl)-1H-1,2,4-triazole
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanon
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1h-1,2,4-triazol-1-yl)butanone
1H-1,2,4-Triazole, 1-((tert-butylcarbonyl-4-chlorophenoxy)methyl)-
3，3-dimethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-1-butanone
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one
1-(4-Chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazo-1-yl) butan-2-one
2-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)-2-BUTANONE
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazole-1-yl)-2-butanone
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl) butan-2-one
3,3-dimethyl-1-(1H-1,2,4-triazole-1-yl)-1- (4-chlorophenoxy)butan-2-one
2-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-
(1R)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone
triadimefon (ISO) 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butanone
Triadimefon:1-(4-Chlorophenoxy)-3,3-Dimethyl-1-(1-H-1,2,4-Triazol-1-Yl)-2-Butanone
1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOLE -1-YL)-2-BUTANONE/TRIADIMEFON | [EINECS(EC#)]
256-103-8 | [Molecular Formula]
C14H16ClN3O2 | [MDL Number]
MFCD00055506 | [MOL File]
43121-43-3.mol | [Molecular Weight]
293.75 |
| Hazard Information | Back Directory | [Uses]
antifungal, P450 inhibitor | [Uses]
Triadimefon is an triazole fungicide is used for the management of mango powdery mildew in South Gujarat. | [Uses]
Systemic agricultural fungicide. | [General Description]
Colorless to pale yellow crystalline solid with a slight odor. | [Air & Water Reactions]
Insoluble in water. | [Reactivity Profile]
Triadimefon is incompatible with strong oxidizing agents and acids. Reacts with acid halides and anhydrides. Also reacts with most active hydrogen compounds . | [Fire Hazard]
Flash point data for Triadimefon are not available; however, Triadimefon is probably combustible. | [Description]
Triadimefon has been a widely used fungicide on crops and
nonfood products since the early 1970s. The metabolite triadimenol
is also active and is registered separately for use as
seed treatment. Triadimenol has a broad regulatory toxicology
database, but its toxicity is considered to be encompassed in
that of triadimefon and therefore the same study was used by
the United States Environmental Protection Agency (US EPA)
in establishing regulatory levels for both pesticides. In
nontarget species, dopaminergic neurotoxicity is the primary
effect, but with chronic exposures its toxicities include hepatic,
carcinogenic, developmental, and reproductive effects. | [Definition]
ChEBI: 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one is a member of the class of triazoles that is 1-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one in which the hydroxyl hydrogen is replaced by a 4-chlorophenyl group. It is a member of triazoles, a member of monochlorobenzenes, an aromatic ether, a ketone and a hemiaminal ether. | [Agricultural Uses]
Fungicide: Triadimefon is a systemic fungicide that is used to
control powdery mildews, rusts, and other fungi on coffee,
seed grasses, cereals, fruits, grapes, vegetables, vines,
pineapple, sugar cane, sugar beets, turf, shrubs, and trees.
Not approved for use in EU countries. Registered for
use in the U.S.
U.S. Maximum Allowable Residue Levels for Triadimefon | [Trade name]
ACCOST®; ACIZOL®; AMIRAL®;
BAY® 6681-F; BAYLETON®; BAY®-MEB-6447;
BAYER® 6681-F; BAYER® MEB-6447; MEB 6447®;
PRO-TEK®; ROFON® | [Pharmacology]
Triadimefon (36) and its alcohol analog triadimenol
(37) have been intensively investigated to determine
the influence of their enantiomeric difference on
fungicidal activity. Between stereoisomeric triadimefon,
no significant difference is observed in their fungicidal
activity. However, triadimenol, which shows a much
higher fungicidal activity than triadimefon, exhibits a clear stereochemistry-dependent activity difference.
Greater fungicidal activity is possessed by the (1S,
2R)-isomer (28). | [Environmental Fate]
Soil. In a culture study, the microorganism Aspergillus niger degraded 32% of tri-
adimefon to triadimenol after 5 days (Clark et al., 1978).
Plant. In soils and plants, triadimefon degrades to triadimenol (Clark et al., 1978;
Rouchaud et al., 1981). In barley plants, triadimefon was metabolized to triadimenol and
p-chlorophenol (Rouchaud et al., 1981; Rouchaud, 1982). In the grains an
Photolytic. When triadimefon was subjected to UV light for one week, p-chlorophenol,
4-chlorophenyl methyl carbamate and a 1,2,4-triazole formed as products (Clark et al.,
1978). | [Metabolic pathway]
Enzymic reduction of triadimefon is an important pathway in plants, soils
and fungi and may be regarded as an activation process, which produces
fungicidally active triadimenol. Two diastereoisomers of triadimenol, A
and B [( 1RS,2SR)-l-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)
butan-2-ol is referred to as diastereoisomer A; 1RS,2RS- is referred to as
diastereoisomer β], are produced in different amounts by plants and fungi
and the proportions may differ within the plant. Similar metabolic pathways
are followed in mammals where reduction of the keto group yields
triadimenol as the principal metabolite and oxidation of the butyl group
gives alcohol and carboxylic acid derivatives. | [Degradation]
Triadimefon is stable to hydrolysis with a DT50 of more than 1 year at pH
3,6 and 9 (22 °C).
On photolysis in methanol in borosilicate glass apparatus using a
medium pressure mercury lamp, triadimefon undergoes cleavage of the
C-1-N bond giving 1,2,4-triazole (2), 4-chlorophenyl methyl carbonate
(3) and 4-chlorophenol(4) (Clark et al., 1978) (Scheme 1).
Sensitised photolysis of triadimefon irradiated by light from a highpressure
mercury lamp, with a Pyrex filter to exclude wavelengths below
290 nm, in the presence of fulvic acid and humic acid gave a variety of
products. In water, the products formed were 4 and a dihydroxychlorobenzene
(5). Although there are some ambiguities in the report concerning
the allocation of structures to the compounds obtained, these included a dihydroxybenzaldehyde (6) and 5-chlorosalicylaldehyde (7). Major
products in the presence of fulvic acid were 4 and a dihydroxychlorobenzene
(5). In the presence of humic acid 4,5, a dihydroxybenzaldehyde
(6) and 1-phenoxy-33-dimethyl-1- ( 1H-1,2,4-triazol-l- yl) -2-butanone (8)
were formed (Moza et al., 1995). | [Toxicity evaluation]
Triadimefon inhibits the lanosterol demethylase, thereby
interfering with ergosterol synthesis that is necessary for the
integrity of fungal cell walls. This action confers specificity for
fungi over vertebrates; however, by a similar mechanism
triazoles have been reported to disrupt steroid and cholesterol
metabolism in mammals. Perturbations of fatty acid, steroid,
and xenobiotic metabolism pathways in liver through specific
nuclear signaling pathways (constitutive androstane receptor
(CAR) and pregnane X receptor (PXR)) have been suggested to
contribute to the observed reproductive and hepatic toxicities.
Triadimefon also both inhibits and induces specific hepatic
cytochrome P-450 enzymes. A series of studies comparing
triadimefon with other two conazoles (propiconazole and
myclobutanil) have shown different modes of action in terms
of carcinogenicity, hepatotoxicity, and developmental and
reproductive toxicities.
Studies in several species have shown that neurotoxicity is the
endpoint of concern with both acute and repeated exposures to
triadimefon and triadimenol. Triadimefon causes accumulation
of synaptic dopamine, both in vivo and in vitro. Pharmacological
challenges and neurochemical studies have shown that
triadimefon blocks dopamine reuptake by binding to the
dopamine transporter in a manner similar to other indirect
dopamine agonists, such as cocaine and d-amphetamine. |
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