Description
Fluazinam is a protective broad-spectrum contact fungicide registered for agricultural use to control various soil-borne fungal pathogens on a variety of crops, such as peanuts, potatoes, beans, etc. It can be applied as a foliar spray or soil treatment, which is effective against a number of diseases caused by pathogenic fungi such as gray mold, downy mildew, melanose, scab, alternaria blotch, clubroot, sclerotinia blight, white root rot, violet root rot. Besides, it shows acaricidal property, which can fight against mites in citrus.
However, as a protective agent, fluazinam is neither systemic or curative, which functions by inhibiting spore germination and spore growth, and also the development of infection structures, thereby giving it protective action with a good residual effect. The anti-fungal property of fluazinam acts by disrupting the energy production of the fungus at multiple sites and therefore preventing resistance.
Toxicology & Ecotoxicology
Rat LD50 (oral) :4,500 mg/kg (m), 4,100 mg/kg (f)
Rat LD50 (dermal) :> 2,000 mg/kg bw (m/f)
Rat LC50 (inhalation) :> 1.1 mg/L (m/f)
Skin irritation :mild irritant (rabbit)
Eye irritation :irritant (rabbit)
Skin sensitization :sensitizer (guinea pig)
Avian LD50 (acute oral) :> 4,190 mg/kg (mallard duck, m/f)
Avian LD50 (acute oral) :> 1,782 mg/kg (quail, m/f)
Fish LC50 :0.11 mg/L (rainbow trout, 96h)
Bee LD50 (oral) :> 100 μg/bee
Bee LD50 (contact) :> 100 μg/bee
Daphnia magna EC50 :0.19 mg/L (48 h)
Environmental Fate
Soil
Half-life- Aerobic = 132 days
Adsorption - Low mobility with Koc values ranged from 1705-2316
Persistence- Total fluazinam residues (fluazinam and its transformation products) are persistent in most environments and are likely to reach aquatic media through runoff. Fluazinam has the potential to bioaccumulate in fish.
Water
Half-life via hydrolysis - Stable at pH 5; 42 days at pH 7; and 6 days at pH 9
Surface water - Fluazinam and its transformation products are moderately persistent and may present concerns for transport to surface water by spray drift or runoff (especially in soils with low organic content)
Groundwater - Fluazinam should not leach substantially to groundwater.
Air
Volatilization- Fluazinam has a low vapor pressure 1.73 x 10-7 mm Hg and is not likely to substantially volatilize.
Degradates
Fluazinam may photolyze relatively rapidly in water (2.5 days) to form a tricyclic compound (G-504). Degradates were included in the drinking water risk assessment. The total fluazinam residues are persistent in most environments and are likely to reach aquatic media as a totality through runoff. The total residues may reach adjacent water bodies via runoff events and may be persistent.
Label use requirements are designed to mitigate related risk concerns
References
https://en.wikipedia.org/wiki/Fluazinam
http://www.agchemaccess.com/Fluazinam
http://www.galchimia.com/chemical-catalog/pesticide-impurities-and-metabolites/fluazinam-standard/
http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/325.htm
Description
Fluazinam, with a LogP of 3.56, has very low
solubility in water (1.7 mgL1, pH6.8, 25C) but higher
solubilities in organic solvents (e.g., acetone 470 g/L,
dichloromethane 330 g/L, ethanol 150 g/L, all at 20 C).
The active ingredient forms light yellow crystals with an
MP of 115 to 117 C and has a vp of 1.5 mPa (25 C). The
compound is stable to acid, alkali, and heat (5).
Chemical Properties
yellow crystal mp 115 ~ 117°C
Uses
Fluazinam is a broad spectrum fungicide. Fluazinam is commonly used for control of Sclerotinia blight and other soilborne pathogens of peanut as well for the control of potato blight.
Uses
Fluazinam is a fungicide with a protective action but with little
curative or systemic activity. It is used to control grey mould and downy
mildew on vines, apple scab, southern blight and white mould on peanuts
and Phytophthora infestans and tuber blight on potatoes. It is also used
against clubroot on crucifers, rhizomania on sugar beet and mites in
apples.
Definition
ChEBI: Fluazinam is a member of the class of aminopyridines that is 2-amino-5-(trifluoromethyl)pyridine in which one of the amino hydrogens is replaced by a 3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl group. A fungicide used to control grey mould, downy mildew and other fungal pathogens. It has a role as an apoptosis inducer, an allergen, a xenobiotic, an environmental contaminant and an antifungal agrochemical. It is a C-nitro compound, a chloropyridine, an aminopyridine, a secondary amino compound, a member of monochlorobenzenes and a member of (trifluoromethyl)benzenes.
Production Methods
Fluazinam is commercially produced through a multi-step synthesis involving the construction of a pyridinamine-based structure. The process typically begins with the preparation of halogenated aromatic intermediates, for example chlorinated and trifluoromethylated nitrobenzene, which are then coupled with substituted pyridines using amination and condensation reactions.
General Description
Fluazinam is a 2,6-dinitroaniline protectant fungicide, which belongs to the pyridinamine group. It can mostly find applications in agriculture.
Hazard
Moderately toxic by ingestion and inhalation. A reproductive hazard.
Agricultural Uses
Fungicide: Used to control Sclerotinia blight on peanuts and
late blight and white mold on potatoes.
Trade name
FLUAZINAM 50 WP®; FROWNCIDE®;
IKF-1216®; ICIA-192®; OMEGA; PP-192®; SHIRLAN®
Contact allergens
Fluazinam is a pesticide with a broad spectrum of anti fungal activity. It caused sensitization in employees in
the tulip bulb industry and in farmers. Fluazinam
induced contact dermatitis in a worker in a plant where
it was manufactured.
Safety Profile
Moderately toxic by
ingestion and inhalation. Experimental
reproductive effects. When heated to
decomposition it emits toxic vapors of NOx,
F-, and Cl-.
Metabolic pathway
Fluazinam may typically be applied to crops of potatoes using up to 10
applications each of 150 g ha
-1. Routes of degradation involve ring
hydroxylation in aerobic soils and reduction of the nitro groups in flooded
soils. A large amount of unextractable residue was observed. In potatoes
and rats, important reactions involve the reduction of nitro groups and
the formation of conjugates. In plants, the trifluoromethyl substituents are
hydrolysed to carboxylic acid groups. Most of the information presented
below was taken from an evaluation of the fungicide published by the UK
Pesticide Safety Directorate (PSD, 1994).
Degradation
Fluazinam is stable to acid, alkali and heat (PM). The DT
50 values for
hydrolysis in buffer solutions held in the dark at 22 °C were 42 and 5.6
days at pH 7 and 9, respectively. There was no appreciable hydrolysis at
pH 5. The major reaction involved hydrolysis of a trifluoromethyl group
to give the nicotinic acid derivative (2). The DT
50 values of fluazinam in
buffer solutions exposed to natural sunlight were in the range 2-3 days.
Up to 11 products were separated but only the major product formed at
pH 9, the nicotinic acid derivative (2), was characterised (PED, 1994).
Pesticide Type
Fungicide; Acaricide
