Fluazinam Chemical Properties

Melting point:

100-102°

Boiling point:

376.1±42.0 °C(Predicted)

Density 

1.766±0.06 g/cm3(Predicted)

vapor pressure 

1.5 x 10^-3 Pa (25 °C)

Flash point:

2 °C

storage temp. 

2-8°C

solubility 

DMF:25.0(Max Conc. mg/mL);53.75(Max Conc. mM)
DMSO:25.0(Max Conc. mg/mL);53.75(Max Conc. mM)
Ethanol:15.0(Max Conc. mg/mL);32.25(Max Conc. mM)
PBS (pH: 7.2):0.25(Max Conc. mg/mL);0.54(Max Conc. mM)

pka

7.11(at 25℃)

form 

Solid

Water Solubility 

1.7 mg l^-1 (25 °C)

color 

Light yellow to Amber to Dark green

Merck 

14,4117

BRN 

4772672

InChIKey

UZCGKGPEKUCDTF-UHFFFAOYSA-N

LogP

3.560

CAS DataBase Reference

79622-59-6(CAS DataBase Reference)

EPA Substance Registry System

Fluazinam (79622-59-6)

Safety Information

Hazard Codes 

T;N,N,T,Xn,F

Risk Statements 

23-41-43-50/53-36-20/21/22-11-38-20-63

Safety Statements 

26-36/37/39-45-60-61-36/37-16-63-57-56-38-28-27-24/25-20/21-13

RIDADR 

UN 2811

WGK Germany 

3

RTECS 

UR8085000

HazardClass 

6.1

PackingGroup 

II

HS Code 

29333990

Hazardous Substances Data

79622-59-6(Hazardous Substances Data)

Fluazinam Usage And Synthesis

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.

uses

Fluazinam is a pyridinamine fungicide that can control blight caused by Phytophthora infestans in potatoes, beans and other crops (e.g., bushberries, edible-podded beans and cruciferous vegetables such as cabbage and broccoli). Fluazinam has strong persistence of effect against blight and can suppress secondary infection in the field through inhibition of sporulation. Fluazinam has been widely used in the U.S. since the 1990s. Fluazinam is not registered for use in California. Exposure in California would occur mainly through crops imported from other states.

Mode of Action

Fluazinam has a multi-site mode of action that disrupts energy production in fungi. Fluazinam has great protective activity, and while it has limited curative or systemic activity, it possesses very good residual effect and rain fastness.
FRAC code: 29

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 mgL?1, pH6.8, 25?C) 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, discovered and developed by ISK, is a highly active fungicide with broad spectrum activity, including soil borne diseases. Furthermore, it has acaricidal activity. Fluazinam is a multi-site contact fungicide that belongs to the pyridinamine family. Fluazinam has launched in several countries since its commercialization in the early 1990's. Now Fluazinam has established a strong presence in potato late blight, soybean white mold or turf fungicide market.

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.

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 DT₅₀ 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 DT₅₀ 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).

Fluazinam(79622-59-6)Related Product Information

• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• N,N-Dimethylaniline
• PHENYL VALERATE
• Phenylhydrazine
• 2-Chloro-5-chloromethylpyridine
• Epichlorohydrin
• N-Methyl-4-nitroaniline
• 4-Methylpyridine
• Chloroacetic acid
• 4-Chloro-2-nitroaniline
• 4-Nitroaniline
• 2-Nitroaniline
• Difluorochloromethane
• 5-CHLORO-4-METHYL-2-NITROANILINE
• 4-AMINO-3,5-DINITROBENZOTRIFLUORIDE
• 2-Chloro-5-nitrobenzotrifluoride
• 2-Chloro-3,5-dinitrobenzotrifluoride
• 4-AMINO-2-CHLOROBENZOTRIFLUORIDE