79622-59-6 Usage
Description
Fluazinam is a protective broad-spectrum contact fungicide with low solubility in water and higher solubility in organic solvents. It belongs to the pyridinamine family and is effective against various soil-borne fungal pathogens and mites in agricultural applications.
Used in Agricultural Industry:
Fluazinam is used as a fungicide for controlling soil-borne pathogens on a variety of crops, such as peanuts, potatoes, beans, etc., for preventing diseases caused by pathogenic fungi like gray mold, downy mildew, melanose, scab, alternaria blotch, clubroot, sclerotinia blight, white root rot, and violet root rot.
Fluazinam is also used as an acaricide to fight against mites in citrus.
Used in Potato Industry:
Fluazinam is used as a fungicide for controlling potato blight and tuber blight on potatoes.
Used in Peanut Industry:
Fluazinam is used as a fungicide for controlling Sclerotinia blight and other soilborne pathogens of peanut.
Used in Vine and Apple Industry:
Fluazinam is used as a fungicide for controlling grey mold and downy mildew on vines, and apple scab.
Used in Crucifer and Sugar Beet Industry:
Fluazinam is used as a fungicide for controlling clubroot on crucifers and rhizomania on sugar beet.
Used in Turf Fungicide Market:
Fluazinam is used as a broad-spectrum fungicide for controlling various fungal diseases in turf management.
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/beeBee LD50 (contact) :> 100 μg/beeDaphnia magna EC50 :0.19 mg/L (48 h)
Environmental Fate
SoilHalf-life- Aerobic = 132 daysAdsorption - Low mobility with Koc values ranged from 1705-2316Persistence- 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.WaterHalf-life via hydrolysis - Stable at pH 5; 42 days at pH 7; and 6 days at pH 9Surface 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.AirVolatilization- Fluazinam has a low vapor pressure 1.73 x 10-7 mm Hg and is not likely to substantially volatilize.DegradatesFluazinam 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
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).
Check Digit Verification of cas no
The CAS Registry Mumber 79622-59-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,6,2 and 2 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 79622-59:
(7*7)+(6*9)+(5*6)+(4*2)+(3*2)+(2*5)+(1*9)=166
166 % 10 = 6
So 79622-59-6 is a valid CAS Registry Number.
InChI:InChI=1/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)
79622-59-6Relevant articles and documents
Method for synthesizing fluazinam
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Paragraph 0012; 0026-0028; 0030-0032; 0034-0036; 0038; ..., (2022/01/05)
The invention discloses a method for synthesizing fluazinam. The method comprises the following steps: S1, enabling 2-amino-3-chloro-5-trifluoromethylpyridine, 4-chloro-3, 5-dinitrobenzotrifluoride, acetonitrile and an alkaline reagent to react for 30 minutes, and heating and refluxing for 4-6 hours; s2, cooling to room temperature, filtering, washing with acetonitrile, heating filtrate to 40 DEG C, slowly adding a chlorination reagent, reacting at 40 DEG C for 3 hours, heating and refluxing for 2 hours, and discharging acidic gas; s3, when acetonitrile is distilled out of the reaction liquid, stopping distillation, adding water, filtering and drying, and obtaining fluazinam. According to the method, weak alkali is used for participating in the reaction, 4-chloro-3, 5-dinitrobenzotrifluoride cannot be hydrolyzed, so that a toxic substance M465 cannot be generated, the content and yield of the fluazinam product prepared through the method are very high, the preparation method is simple, the process is reasonable, cost is saved, and no waste gas is generated.
Method for synthesizing fluazinam (by machine translation)
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Paragraph 0016-0018, (2019/08/12)
The method comprises the following steps: (1) reacting 2 - amino -3 - chlorine -5 - trifluoromethylpyridine and 2, 4 - dichloro -3, 5 -dinitrobenzotrifluoride under the presence of an inorganic base to pH 2, and (1) recrystallizing -toluidine hydrochloride α - α -trifluoro 2 - 6, 85%~95% dinitro- p-toluidine as a recrystallization solvent. (3 -) A fluazinam is obtained by recrystallization using an aqueous ethanol solution having a content 3 - of ethanol as 60%~90% a recrystallization solvent after the reaction; and step (b) . the mixture is obtained.2 α 6 - alpha.trifluoromethyl -5 - pyridyl) - α 3, alphaωdinitrohexafluorobenzoic acid is a mixture of N- (-2 -)-N-methyl-p-98% methyl-p-trifluoromethylbenzylamine. In the method, an ether solvent with lower toxicity is selected; the reaction molar yield is high, the content of related impurities is lower than one-tenth, α - crystal form crystal fluazinam is obtained, and subsequent preparation processing. (by machine translation)
Preparation method of fluazinam
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Paragraph 0047; 0048; 0049; 0050; 0051; 0052; 0053-0080, (2017/04/29)
The invention provides a preparation method of fluazinam. Fluazinam is prepared through a reaction of 2-amino-3-chloro-5-trifluoromethylpyridine and 2,4-dichloro-3,5-dinitrobenzotrifluoride with an inorganic alkali as an alkali and 2-methyltetrahydrofuran as a solvent. The preparation method of fluazinam, adopting 2-methyltetrahydrofuran as the solvent has the advantages of good reaction selectivity, short reaction time, substantial improvement of the productivity of every device, large productivity, suitableness for industrial production, small use amount of the solvent, mild reaction conditions, simplicity in operation, great simplification of the industrial process, and realization of obviously less hydrolysis byproduct due to the poor compatibility with water, and allows the highest mole yield to reach 98.4% and the highest purity to reach 99.8%.
