Fluazinam

465.09200

465.09

616-712-5

0P91PCK33Q

DTXSID7032551

Light yellow crystals

2933399053

116.56000

7.10540

Light yellow crystals

1.766 g/cm3

113 °C

376.1ºC at 760 mmHg

181.3ºC

1.571

In water, 1.35X10-1 mg/L at 20 deg C

2-8ºC

1.5 x 10 -3 Pa (25 °C)

Pungent at 23 °C

pH = 5.8 at 25 °C (1% aqueous solution)

Henry's Law constant = 2.5X10-4 atm-cu m/mol at 25 °C /Estimated/

pKa = 7.34 at 20 °C

183.51 Ų [M-H]-

Hydroxyl radical reaction rate constant = 6.6X10-14 cu cm/molecule-sec at 25 °C /Estimated/

No visible changes in commercial packaging (polyethylene jugs) following storage at 50 °C for 91 days. No physical changes in plastic containers after 12 months at 25 °C.

UN 2811

3

R23; R41; R43; R50/53

S26-S36/37/39-S45-S60-S61

UR8085000

T; N

Storage stability: No change in active content (before and after storage: 41.4%, 41.5%) over 12 months at 25 deg C and 50% humidity. /Allegro 500F/ /from table/

P201-P261-P273-P280-P304 + P340 + P312-P305 + P351 + P338 + P310

H315-H318-H332-H361d-H410

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.

Health Canada, Pest Management Regulatory Agency; Regulatory Note- Fluazinam REG2003-12 (October 27, 2003). Available from: http://www.pmra-arla.gc.ca/english/pdf/reg/reg2003-12-e.pdf as of October 20, 2004.

|Danger|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P333+P313, P363, P391, P405, and P501|H315 (13%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P332+P313, P333+P313, P362, P363, P391, P405, and P501|Aggregated GHS information provided by 326 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P333+P313, P337+P313, P363, P403+P233, P405, and P501

Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear. Waterproof hat and boots.

LD50 Rat oral >5000 mg/kg|LD50 Rabbit dermal >2000 mg/kg

/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.

Fluazinam's production may result in its release to the environment through various waste streams; it's use as a fungicide(1) will result in its direct release to the environment(SRC).

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).

The rate constant for the vapor-phase reaction of fluazinam with photochemically-produced hydroxyl radicals has been estimated as 6.6X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 240 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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(2,3). The major hydrolysis product is 5-chloro-6-(3-chloro-alpha, alpha, alpha-trifluoro-2,6-dinitro-p-toluidino)nicotinic acid(2,4). This substance is also expected to undergo direct photolysis based on a measured aquatic photolysis half-life of 2.5 days(2,3). The measured photolysis half-life of fluazinam in soil was 22 days compared to 69 days for the dark control(2).

Measured BCF values for fluazinam in fish were 348 for fillet, 1220 for whole fish, and 1850 for viscera(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is high to very high(SRC), provided the compound is not altered physically or chemically once released into the environment.

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).

The Henry's Law constant for fluazinam is estimated as 2.5X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 5.6X10-5 mm Hg(1), and water solubility, 1.35X10-1 mg/L(1). This Henry's Law constant indicates that fluazinam is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 11 days(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(3). Fluazinam's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Fluazinam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to fluazinam may occur through inhalation and dermal contact with this compound at workplaces where fluazinam is produced or used(SRC). Exposure studies indicate that field workers may be exposed to fluazinam during mixing, loading, and application activities involving this substance(1,2). Inhalation exposure levels for operators applying fluazinam to potato fields ranged from 0.58 to 9.76 ug/kg during mixing and loading and from 1.2 to 1.4 ug/kg during application(2). Dermal exposure levels measured in this study ranged from 280.48 to 680.42 ug/kg during mixing and loading and from 281.73 to 315.27 ug/kg during application(2).

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.

... Fluazinam was almost completely metabolized /in treated rats/ by hydroxylation, followed by conjugation. A quantitative sex difference was not observed.

Fluazinam is a lipophilic weak acid with strong uncoupling activity on mitochondria in vitro.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/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.

3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine

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/

Preparation: R. Nishiyama et al., EP 31257; eidem, US 4331670 (1981, 1982 both to Ishihara Sangyo Kaisha).

Agrochemicals -> Fungicides|Acaricides, Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Fluazinam has known environmental transformation products that include 5-((3-chloro-5-(trifluoromethyl)-2-pyridyl)amino)-alpha,alpha,alpha-trifluoro-4,6-dinitro-o-cresol.|Fluazinam has known environmental transformation products that include DAPA compound VIII, HYPA compound XII, and MAPA compound VII.