79622-59-6 Usage
Description
Different sources of media describe the Description of 79622-59-6 differently. You can refer to the following data:
1. 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.
2. 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).
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/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
Chemical Properties
yellow crystal mp 115 ~ 117°C
Uses
Different sources of media describe the Uses of 79622-59-6 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
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).
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
-
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.
Synthetic process of fluazinam
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Paragraph 0021; 0025-0028; 0032-0035; 0036-0040; 0047-0050, (2019/08/31)
The invention discloses a synthetic process of fluazinam, and belongs to the technical field of pesticide chemical engineering. The process comprises the following steps: taking 2-halogen-3-chloro-5-trifluoromethyl pyridine and ammonia gas as raw materials to carry out an amination reaction in an ether solvent in a high-pressure kettle, carrying out desalination and deamination on the reaction liquid, then carrying out a condensation reaction with 2,4-dichloro-3,5-binitro-trifluorotoluene under an alkaline condition, and carrying out a conventional post-treatment method to obtain the fluazinam. According to the invention, in a continuous process of the two-step process, generation of side reactions of 2,4-dichloro-3,5-binitro-trifluorotoluene during the condensation reaction due to ammoniaresidues in an amine solution is avoided, so that unit consumption of the 2,4-dichloro-3,5-binitro-trifluorotoluene is reduced to a stoichiometric ratio, and product purification and yield are greatly improved. The product does not need to be purified, the purity can reach 99% or above, and the total separation yield of two steps can reach 97% or above.
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%.
