ChemicalBook CAS DataBase List 79622-59-6

79622-59-6

Name	Fluazinam
CAS	79622-59-6
EINECS(EC#)	200-835-2
Molecular Formula	C13H4Cl2F6N4O4
MDL Number	MFCD00214168
Molecular Weight	465.09
MOL File	79622-59-6.mol

Synonyms

3-chloro-n-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2-pyridinamine 3-CHLORO-N-(3-CHLORO-2,6-DINITRO-4-TRIFLUOROMETHYLPHENYL)-5-TRIFLUOROMETHYL-2-PYRIDYLAMINE 3-CHLORO-N-(3-CHLORO-5-TRIFLUOROMETHYL-2-PYRIDYL)-ALPHA,ALPHA,ALPHA-TRIFLUORO-2,6-DINITRO-P-TOLUIDINE FLUAZINAM FROWNCIDE SHIRLAN 3-chloro-n-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2-pyridinamin 3-chloro-n-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-2-pyridinamin 6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-n-(5-chloro- asc66825 asc67178 ikf1216 pp192 shirlan(zeneca) shirlanflow 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluor-2,6-dinitro-p-toluidine fluaziname FLUAZINAM SOLUTION 3-Chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-2,6-dinitro-p-toluidine 2-Pyridinamine, 3-chloro-N-3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl-5-(trifluoromethyl)-

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)
Fp	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)
form	neat
pka	7.11(at 25℃)
Water Solubility	1.7 mg l^-1 (25 °C)
color	Light yellow to Amber to Dark green
Merck	14,4117
BRN	4772672
Henry's Law Constant	3.9×10^-2 mol/(m³Pa) at 25℃, HSDB (2015)
Major Application	agriculture environmental
InChI	1S/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23)
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. less more
InChIKey	UZCGKGPEKUCDTF-UHFFFAOYSA-N
SMILES	[O-][N+](=O)c1cc(c(Cl)c(c1Nc2ncc(cc2Cl)C(F)(F)F)[N+]([O-])=O)C(F)(F)F
LogP	3.560
CAS DataBase Reference	79622-59-6(CAS DataBase Reference)
EPA Substance Registry System	79622-59-6(EPA Substance)

Safety Data

Symbol(GHS)	GHS05,GHS07,GHS08,GHS09
Signal word	Danger
Hazard statements	H317-H318-H332-H361d-H410
Precautionary statements	P273-P280-P302+P352-P304+P340+P312-P305+P351+P338-P308+P313
Hazard Codes	T;N,N,T,Xn,F
Risk Statements	R23:Toxic by inhalation. R41:Risk of serious damage to eyes. R43:May cause sensitization by skin contact. R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . R36:Irritating to the eyes. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R11:Highly Flammable. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S60:This material and/or its container must be disposed of as hazardous waste . S61:Avoid release to the environment. Refer to special instructions safety data sheet . S36/37:Wear suitable protective clothing and gloves . S16:Keep away from sources of ignition-No smoking . less more
RIDADR	UN 2811
WGK Germany	3
RTECS	UR8085000
HazardClass	6.1
PackingGroup	II
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Inhalation Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1 Repr. 2 Skin Sens. 1
Safety Profile	Moderately toxic by ingestion and inhalation. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx, F-, and Cl-. less more
Hazardous Substances Data	79622-59-6(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

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.

Definition

ChEBI: 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 fu gal pathogens.

Uses

Agricultural fungicide.

Hazard

Moderately toxic by ingestion and inhalation. A reproductive hazard.

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.

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®

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).

storage

Store at -20°C

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).

Pesticide Type

Fungicide; Acaricide

Questions And Answer

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 ;

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79622-59-6

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Hazard Information

Chemical Properties

Uses

Definition

Uses

Hazard

Production Methods

General Description

Agricultural Uses

Trade name

Metabolic pathway

storage

Degradation

Pesticide Type

Questions And Answer

Description

Toxicology & Ecotoxicology

Environmental Fate

References

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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