79622-59-6O=[N+]([O-])c1cc(C(F)(F)F)c(Cl)c([N+](=O)[O-])c1Nc1ncc(C(F)(F)F)cc1ClUZCGKGPEKUCDTF-UHFFFAOYSA-NFluazinam 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 a xenobiotic, an allergen, an apoptosis inducer, an environmental contaminant and an antifungal agrochemical. It is a C-nitro compound, an aminopyridine, a chloropyridine, a secondary amino compound, a member of monochlorobenzenes and a member of (trifluoromethyl)benzenes.
79622-59-6Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
Acaricides, Fungicides
Pesticide (Fluazinam) -> USDA PDB
log Kow = 4.1
3.27
Solubility in n-hexane 12, acetone 470, toluene 410, diethyl ether 320, dichloromethane 330, ethanol 150 (all in g/L, 20 °C)
Solubility in methanol 162 g/L, dichloroethane 485 g/L, ethyl acetate 624 g/L
In water, 1.35X10-1 mg/L at 20 °C
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Danger
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P261, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 1.4% (3 of 217) of reports.
Danger
H315 (32.3%): Causes skin irritation [Warning Skin corrosion/irritation]
Commission Regulation (EC) No 1490/2002
Fluazinam is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Dir. 2008/108, Reg. (EU) 2019/168, Reg. (EU) 2019/2094, Reg. (EU) 2021/2068, Reg. (EU) 2021/52, Reg. (EU) 2024/324, Reg. (EU) No 2023/114, Reg. (EU) No 540/2011
Fluazinam: HSNO Approval: HSR002852 Approved with controls
Allergic contact dermatitis reported in manufacturing and farming workers; [Kanerva, p. 1796] Reports of skin irritation and sensitization in agricultural employees; [HSDB] Toxic to the liver in animal experiments; [Reference #2] May cause serious eye injury; May cause skin sensitization; Toxic by inhalation; [Aldrich MSDS]
Tolerances are established for residues of fluazinam, (3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-2-pyridinamine) in or on the following commodities: peanut; and potato.
Metabolites AMPA /(4-chloro-N2-[3-chloro-5- (trifluoromethyl)-2-pyridyl]-3-nitro-5-(trifluoromethyl)-1,2-benzenediamine)/, DAPA /(3-chloro-2-(2,6-diamino-3-chloro-alpha,alpha,alpha- trifluoromethyl) pyridine)/, and some related conjugates and hydrolysis products were isolated, identified and characterized from urine, feces and bile of radiolabelled fluazinam-treated rats. Fluazinam was almost completely metabolized by hydroxylation, followed by conjugation. A quantitative sex difference was not observed.
In a metabolism study in rats, only 33-40% of the administered dose of radio labeled fluazinam was absorbed. Most of the administered dose was recovered in the feces (>89%). Unabsorbed parent compound represented most of the identified radioactivity in the feces. Excretion via the urine was minor (<4%). Total biliary radioactivity, however, represented 25-34% of the administered dose, indicating considerable enterohepatic circulation. Analysis of chromatograms indicated that numerous metabolites were present in the bile.
Used as agricultural fungicide; [Merck Index] Omega 500F: Used in the US as a fungicide for peanuts and potatoes; [Reference #2]
Farming (Pesticides) [Category: Industry]
For fluazinam (USEPA/OPP Pesticide Code: 129098) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Agricultural fungicide
Fungicide; Broad spectrum disease control on Alternaria, Botrytis, Phytophthora/Plasmopara, Sclerotinia,Venturia, and other pathogens. Acaricide on citrus red mites and two spotted spider mites.
Wird geladen…
DTXSID7032551CHEMBL1878267CHEBI:818430.000056 [mmHg]
5.6X10-5 mm Hg at 25 °C
Tolerances are established for residues of fluazinam and its metabolite AMGT 3-[[4-amino-3-[[3-chloro-5-(trifloromethyl)-2-pyridinyl]amino]-2-nitro-6-(trifluoromethyl) phenyl] thio]-2-(beta-D-glucopyranosyloxy) propionic acid) in or on the following commodity: wine grape (No US registration as of March 15, 2002)
Skin Irrit. 2 (32.3%)
Reproductive toxicity - category 2
Acute toxicity (Inhalation: Dusts and mists) - Category 2
Acute toxicity (Inhalation: Dusts and mists) - Category 4
Repr. 2
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Tolerances are established for residues of fluazinam, (3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-2-pyridinamine) in or on the following commodities: peanut 0.02 ppm; and potato 0.02 ppm.
Tolerances are established for residues of fluazinam and its metabolite AMGT 3-[[4-amino-3-[[3-chloro-5-(trifloromethyl)-2-pyridinyl]amino]-2-nitro-6-(trifluoromethyl) phenyl] thio]-2-(beta-D-glucopyranosyloxy) propionic acid) in or on the following commodity: wine grape 3.0 ppm (No US registration as of March 15, 2002)
Fluazinam increases the risks of thyroid gland follicular cell and hepatocellular tumors in rats and mice. According to The Cancer Assessment Review Committee (CARC), there is suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential.
LD50 Colinus virginianus (Bobwhite quail) oral 1782 mg/kg
LD50 Anas platyrhynchos (Mallard duck) oral 4190 mg/kg
LC50 Oncorhynchus mykiss (Rainbow trout, juvenile) 111 ug/L/96 hr (95% confidence interval: 100-130 ug/L); hardness: 50-56 mg/L CaCO3, flow through
LC50 Oncorhynchus mykiss (Rainbow trout, juvenile) 36 ug/L/96 hr (95% confidence interval: 33-56 ug/L); hardness: 28-30 mg/L CaCO3, flow through
For more Ecotoxicity Values (Complete) data for FLUAZINAM (15 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values ranging from 1,705-2,316(2) indicate that fluazinam is expected to have slight to low mobility in soil(SRC). Volatilization of fluazinam from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-4 atm-cu m/mole, based upon its vapor pressure, 5.6X10-5 mm Hg(3) and water solubility, 1.35X10-1 mg/L(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Fluazinam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. The measured photolysis half-life of fluazinam in soil was 22 days compared to 69 days for the dark control(2). Biodegradation is expected in the soil environment with reported half-lives for the degradation of fluazinam in aerobic soil ranging from 9 to 49 days(2). Half lives for the degradation of fluazinam in anaerobic soil range from 4.5 to 32 days(4).
AQUATIC FATE: Based on a classification scheme(1), measured Koc values ranging from 1,705-2,316(2), indicate that fluazinam is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.5X10-4 atm-cu m/mole, based upon its vapor pressure, 5.6X10-5 mm Hg(4) and water solubility, 1.35X10-1 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.1 hours and 11 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 120 days if adsorption is considered(5). The pKa of fluazinam is 7.34(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(6). According to a classification scheme(7), measured BCF values ranging from 348-1850(2) suggest the potential for bioconcentration in aquatic organisms is high to very high(SRC). Fluazinam is expected to undergo hydrolysis in the environment based on measured half-lives of 42 days at pH 7 and 6 days at pH 9(2,4). This substance is also expected to undergo direct photolysis based on a measured aquatic photolysis half-life of 2.5 days(2,4). The measured aerobic and anaerobic aquatic metabolism half-lives of fluazinam have both been reported to be less than or equal to 8 hours(2).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluazinam, which has a vapor pressure of 5.6X10-5 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluazinam is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 240 days(SRC), calculated from its rate constant of 6.6X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase fluazinam may be removed from the air by wet and dry deposition(SRC). Fluazinam is expected to undergo direct photolysis based on a measured aquatic photolysis half-life of 2.5 days(2,4).
/AQUATIC SPECIES/ The 34 day chronic early life stage NOEC for fathead minnow based on mortality and hatching success were 5.3 and 10 ug a.i./L, respectively. The 278 day chronic full life cycle NOEC (F0 generation) values based on survival and reproductive success were 6.4 and 2.9 ug a.i./L, respectively. The NOEC (F1 generation) values based on hatching success was 0.69 ug a.i./L. Based on the results of this study, the most sensitive endpoint was F1 generation hatching success.
/AQUATIC SPECIES/ Chronic toxicity to invertebrates are only represented through the Daphnia magna life cycle where the NOAEC was calculated at 0.068 ppm and the LOAEC at 0.140 ppm. The endpoints affected for this study were reproductive (reduced number of young per female) and growth effects.
/AQUATIC SPECIES/ The fungicide fluazinam, the insecticide lambda-cyhalothrin, and the herbicides asulam and metamitron were applied to indoor freshwater microcosms (water volume approximately 0.6 cu m). ...Concentrations of each pesticide were equal to 0%, 0.2%, 0.5%, 2%, and 5% spray drift emission of label-recommended rates. ...The half-lives of lambda-cyhalothrin, metamitron, and fluazinam were 1 to 2 days; that of asulam was >30 days. ...0.2% treatment regime was considered the community NOEC. The macroinvertebrate populations of Gammarus pulex, Asellus aquaticus, and Proasellus meridianus were the most sensitive end points, followed by species of copepods and cladocerans.
Koc values measured for fluazinam in four types of soils (unspecified) ranged from 1705-2316(1). According to a classification scheme(2), these Koc values suggest that fluazinam is expected to have slight to low mobility in soil. The pKa of fluazinam is 7.34(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4). Fluazinam has been shown to adsorb more strongly in soils that are higher in organic matter(5). During a soil leaching study, 95% of the applied radioactivity remained in the top 5 cm of the soil(6).
/SIGNS AND SYMPTOMS/ There has been a history of skin irritation and sensitization associated with the repeated application of fluazinam in agriculture use.
/CASE REPORTS/ ...Two cases of occupational asthma caused by sensitization to powdered fungicides fluazinam and chlorothalonil, from the same fungicide formulation plant /are reported/. Both developed work related lower respiratory symptoms after a latent interval of asymptomatic exposure.
/SIGNS AND SYMPTOMS/ ...An outbreak of contact dermatitis in a tulip bulb processing company /is described/. Shortly after the introduction of a new pesticide, the fungicide fluazinam, employees started to complain of dermatitis of the arms and the face.
/SIGNS AND SYMPTOMS/ In spring 1992, several farmers in the western part of The Netherlands developed dermatitis on their hands, forearms and face. ...Complaints ranged from a mildly itchy, papular rash to a painful, weeping and blistering dermatitis. Medical aid was needed by 5/9 of them. Some of the farmers had in common that their complaints emerged after repeated application of a new fungicide over several weeks, Shirlan, with fluazinam as its active ingredient.
AEROBIC: Fluazinam was degraded during field dissipation studies conducted in Ephrata, Washington; Kempton, North Dakota; Porterville, California; and Monctezuma, Georgia with dissipation half-lives ranging from 9 to 49 days(1). The measured half-life for the metabolism of fluazinam was reported to be less than or equal to 30 days in a sandy loam soil biodegradation study(1). After 361 days, 6.8 and 9.5% of the applied fluazinam remained intact for the C14-Pyridyl and C14-Phenyl labels, respectively(1). No major degradation products were observed in this study. The measured aerobic aquatic metabolism half-life of fluazinam has been reported to be less than or equal to 8 hours(1).
ANAEROBIC: The measured anaerobic aquatic metabolism half-life of fluazinam has been reported to be less than or equal to 8 hours(1). The half-life of fluazinam was 4.5 days at 1 kg/ha in anaerobic sandy loam (no aerobic pre-incubation) and 32 days at 10 °C and 1 kg/ha in anaerobic sandy loam (aerobic pre-incubation)(2).
Tolerances are established for residues of fluazinam, (3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-2-pyridinamine) in or on the following commodities: peanut; and potato.
Tolerances are established for residues of fluazinam and its metabolite AMGT 3-[[4-amino-3-[[3-chloro-5-(trifloromethyl)-2-pyridinyl]amino]-2-nitro-6-(trifluoromethyl) phenyl] thio]-2-(beta-D-glucopyranosyloxy) propionic acid) in or on the following commodity: wine grape (No US registration as of March 15, 2002)
Control of grey mould and downy mildew on vines; apple scab; southern blight and white mould on peanuts; and Phytophthora infestans and tuber blight on potatoes. Control of clubroot on crucifers, and rhizomania on sugar beet. Applied at 150-750 g/ha.
Wettable powder, suspension concentrate, dustable powder.
Trade names: Omega, Allegro, Altima, Frowncide, Legacy, Ohayo, Shogun
Tradenames: Shirlan; Barclay Cobbler; Mapro; Omego; Sagiterre; Salvo; Sekoya. Mixtures: Epok (+metalaxyl-M).
Allegro 500F Agricultural Fungicide: Formulation type- Water dispersible granule; Guarantee- Fluazinam 40.0% (nominal), certified limits: 38.82-41.23%. /from table/
Acaricides, Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
BeschreibungFluazinam, 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).
VerwendenFluazinam 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.
DefinitionChEBI: 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.