DIFENOCONAZOLE
Fungicide
FRAC 3; DMI: triazole
|
 |
 |
 |
| |
NOMENCLATURE
Common name difenoconazole (BSI, draft E-ISO)
IUPAC name cis,trans-3-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]phenyl
4-chlorophenyl ether
Chemical Abstracts name 1-[2-[4-(4-chlorophenoxy)-2-chlorophenyl]-4-methyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
CAS RN [119446-68-3] unstated stereochemistry Development codes CGA 169 374 (Ciba-Geigy) |
| |
|
 |
|
|
| |
| Composition Ratio of cis- to trans-
isomers is in the range 0.7 to 1.5.
Mol. wt. 406.3
M.f. C19H17Cl2N3O3 Form White to light beige crystals. M.p. 78.6 ºC V.p. 3.3 ´ 10-5 mPa (25 ºC) KOW logP = 4.20 (25 ºC) Henry 1.5 ´ 10-6 Pa m3 mol-1 (calc.) S.g./density 1.40 (20 ºC)
Solubility In water 15 mg/l (25 ºC). In ethanol 330, acetone 610, toluene 490,
n-hexane 3.4, n-octanol 95 (all
in g/l, 25 ºC). Stability Stable up to 150 ºC. Hydrolytically
stable. |
| |
|
|
|
|
| |
APPLICATIONS
Biochemistry Sterol demethylation
inhibitor. Inhibits cell membrane ergosterol
biosynthesis, stopping development of the fungus.
Mode of action Systemic fungicide with preventive and
curative action. Absorbed by the leaves, with
acropetal and strong translaminar translocation.
Uses Systemic fungicide with a novel broad-range activity protecting the yield
and crop quality by foliar application or seed
treatment. Provides long-lasting preventive
and curative activity against Ascomycetes, Basidiomycetes
and Deuteromycete,s including Alternaria, Ascochyta, Cercospora, Cercosporidium, Colletotrichum, Guignardia, Mycosphaerella, Phoma, Ramularia, Rhizoctonia, Septoria, Uncinula, Venturia spp., Erysiphaceae, Uredinales and several
seed-borne pathogens. Used against disease complexes
in grapes, pome fruit, stone fruit, potatoes,
sugar beet, oilseed rape, banana, cereals, rice,
soya beans, ornamentals and various vegetable
crops, at 30-125 g/ha. Used as a seed treatment
against a range of pathogens in wheat and barley,
at 3-24 g/100 kg seed.
Phytotoxicity In wheat, early foliar applications at growth stages 29-42 might cause, in
certain circumstances, chlorotic spotting of
leaves, but this has no effect on yield. Formulation types DS; EC; FS; SC; WG. |
| |
|
|
|
|
|
| ANALYSIS
Residue determination
by glc. Details from Syngenta. |
| |
|
|
|
|
|
| MAMMALIAN
TOXICOLOGY
Oral Acute oral LD50 for rats 1453, mice >2000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits
>2010 mg/kg. Non-irritant to eyes and skin
(rabbits). Non-sensitising to skin (guinea pigs).
Inhalation LC50 (4 h) for rats ³3300 mg/m3 air.
NOEL (2 y) for rats 1.0 mg/kg b.w. daily; (1.5 y)
for mice 4.7 mg/kg b.w. daily; (1 y) for dogs
3.4 mg/kg b.w. daily. ADI 0.01 mg/kg b.w. Other Not teratogenic or mutagenic. Toxicity class WHO (a.i.) III EC hazard (R22) |
| |
|
|
| |
|
|
| ECOTOXICOLOGY
Birds LD50 (9-11 d) for mallard ducks >2150 mg/kg.
LC50 for bobwhite quail >4760, mallard
ducks >5000 ppm.
Fish LC50 (96 h) for rainbow trout 0.8, bluegill
sunfish 1.2, sheepshead minnow 0.82 mg/l.
Daphnia LC50 (48 h) 0.77 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 1.2
mg/l.
Other aquatic spp. EC50 (96 h) for Eastern oysters 0.45 mg/l; (14 d)
for Lemna gibba 18.5 mg/l.
Bees Non-toxic to honeybees; LD50 (oral) >187
mg/bee; LC50 (contact) >100 mg/bee. Worms LC50 for earthworms >610 mg/kg. |
| |
|
|
|
|
|
| |
ENVIRONMENTAL
FATE
Animals After oral administration, difenoconazole was
rapidly eliminated practically to entirety,
with urine and faeces. Residues in tissues were
not significant and there was no evidence for
accumulation. Plants Two routes of metabolism: one by a triazole route to triazolylalanine and
triazolylacetic acid; the other by hydroxylation
of the phenyl ring followed by conjugation.
Soil/Environment Practically immobile in soil, strong adsorption
to soil particles, low potential to leach below
top soil layer. Soil dissipation rate is slow
and dependent on application rate. DT50 for photolysis 145 d (natural sunlight). |
| |
|
|
Products
Products--กทFUNGICIDES