Fluchloralin

355.7

355.70

251-426-0

98UIF19AH9

DTXSID9032614

Orange-yellow solid

2921430033

94.9

5.07 (est)

1.448 g/cm3

42-43 °C

392.3ºC at 760 mmHg

30 DEG C

1.542

In water, 0.9 mg/L at 20 deg C

0-6°C

3X10-5 mm Hg at 20 deg C

Oral-Rat LD50: 2940 mg/kg; Oral-Mouse LD50: 730 mg/kg

Combustion produces toxic nitrogen oxides, chlorides and fluoride gases

FAINT, MEDICINAL ODOR

Henry's Law constant = 1.5X10-5 atm-cu m/mole at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.6X10-11 cu cm/molec-sec at 25 °C (est)

SLIGHTLY CORROSIVE

UN30779/PG3

2

50/53

60-61

XU5160000

N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Storage stability in the original unopened container is guaranteed for 3 to 4 years at normal room temperatures; sensitive to ultraviolet and visible light.

P273

H400

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.|Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or public waters unless this product is specifically identified and addressed in an NPDES permit. ... Do not apply directly to water. Do not contaminate water by cleaning of equipment or disposal of wastes.

|Warning|H400 (92.68%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.

FLAMMABLE

For several good reasons, all of the herbicides mentioned in this chapter /including fluchloralin/ should be handled and applied only with full attention to safety measures that minimize personal contact. Many formulations contain adjuvants (stabilizers, penetrants, surfactants) that may have significant irritating and toxic effects. A number of premixed formulations contain two or more active ingredients; the companion pesticides may be more toxic than the principal herbicide. Good hygienic practice should not be disregarded just because a pesticide is reported to have a high LD50 in laboratory rodents.|Equipment should be rinsed with a solution of detergent and water.|Keep out of lakes, streams, and ponds. Do not apply where runoff is likely to occur.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

May cause slight reddening to skin and eyes.

LOW LEVEL SOIL RESIDUES MAY PERSIST FOR MORE THAN ONE SEASON AFTER APPLICATION, AND PHYTOTOXICITY TO VERY SENSITIVE CROPS MAY OCCUR.

moderately toxic

LD50 Rat oral 1,550 mg/kg

/BIRDS and MAMMALS/ Bird: Low toxicity to wild fowl.|/AQUATIC SPECIES/ Effect of 120 days of continuous exposure of three sublethal concentrations (1/2, 1/4 and 1/8 fractions of 96 hr LC50) of Basalin on alkaline phosphatase (Alk P), acid phosphatase (Acid P), lactic dehydrogenase (LDH), succinic dehydrogenase (SDH), glutamic oxaloacetic transaminase (GOT), and glutamic pyruvic transaminase (GPT) activities in the liver of Nemacheilus denisonii /freshwater fish/ were studied. Alk P, Acid P, LDH, and GPT activities were significantly inhibited, but GOT activities were not significantly altered. More inhibition was observed with the higher concentration, but Acid P, LDH, and GPT activities were significantly inhibited in all three sublethal concentrations.|/AQUATUC SPECIES/ Hazards to fish: High toxicity poses potential threat to fish populations. ... Potential problems with endangered species: USDI has made a jeopardy assessment, finding threats to slackwater darter and 11 freshwater mussels from use of fluchloralin on soybeans.

Fluchloralin's former production and use in the US as a selective pre-planting herbicide(1) resulted in its direct release to the environment(SRC).

(14)C-Fluchloralin was degraded in a loamy sand soil. Degradation products were identified by TLC and GLC and comparison with standard compounds whose structure was confirmed by IR and MS. Degradation products included the following compounds: N-(2-chloroethyl)-2,6-dinitro-4-trifluoromethylaniline, 2,6-dinitro-4-trifluoromethylphenol, 2,6-dinitro-4-trifluoromethylaniline, 1,2-diamino-6-nitro-4-trifluoromethylbenzene, 1,2,3-triamino-5-trifluoromethylbenzene, 2,6-dinitro-N-(2-hydroxypropyl)-N-propyl-4-trifluoromethylaniline, 2,6-dinitro-N-propyl-4-trifluoromethylaniline. ... Some CO was formed and a part of the (l4)C was found in humic acids.|TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 150-550(2) indicate that fluchloralin is expected to have moderate to low mobility in soil(SRC). Volatilization of fluchloralin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3X10-5 mm Hg(3) and water solubility of 0.9 mg/L(4). Volatilization from dry soil surfaces is not expected(SRC) based on the vapor pressure of this compound(3). Fluchloralin degraded 30.4% following application to dry thin layer soil plates and exposure to unfiltered solar radiation for 7 days in July(5). The half-life of fluchloralin in a clay loam (4% sand, 25% silt, 71% clay, 4.2% organic matter) was 52 days at a soil moisture corresponding to the field capacity, but was only 8 days when the soil was flooded(6), suggesting degradation occurs more rapidly under anaerobic conditions(SRC).|TERRESTRIAL FATE: The results of field and laboratory studies conducted over a 3-yr period found that delaying soil incorporation of herbicidal applications of fluchloralin caused important herbicide losses through volatilization and photodecomposition(1); avg losses for delayed incorporation for 1, 3 and 7 days were 11, 29, and 69% respectively(1).|AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 150-550(2) indicate that fluchloralin is expected to adsorb to suspended solids and sediment in the water column. Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3X10-5 mm Hg(4) and water solubility of 0.9 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 103 hours and 54 days, respectively. According to a classification scheme(6) an estimated BCF value of 733(SRC), from an estimated log Kow of 5.07(7) and a regression derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Fluchloralin does not hydrolyze at environmental pH (pH 5-9)(9). Aqueous solutions of fluchloralin exposed to natural sunlight degraded 84 and 97%, after 13 and 48 days of exposure, respectively(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluchloralin, which has a vapor pressure of 3X10-5 mm Hg at 20 °C(1) is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluchloralin 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 about 25 hours(SRC) calculated from its rate constant of 1.6X10-11 cu cm/molecule-sec(SRC), derived using a structure estimation method(3). Fluchloralin absorbs light greater than 290 nm and is susceptible to photolysis in the atmosphere based on its rate of photolysis in aqueous solution(4). Particulate-phase fluchloralin may be physically removed from the air by wet and dry deposition(SRC).

Irradiation of Basalin in methanol-water with a photoreactor yielded nine products. Identification was based mainly on mass spectral data.|The rate constant for the vapor-phase reaction of fluchloralin with photochemically produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 25 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Fluchloralin is stable to hydrolysis over pH range 5-9(2).|The direct photolysis of fluchloralin was examined in 5 ppm aqueous solutions exposed to natural sunlight(1); after 13 and 48 days of exposure, 84 and 97%, respectively, of initial fluchloralin had photolyzed(1); the photolysis products included 2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine, 2,6-dinitro-4-trifluoromethylaniline, and several benzimidazole derivatives(1). Fluchloralin applied to a sandy loam soil was irradiated for a 48-hr period with a photoreactor simulating sunlight; 20% photodegradation was observed(1). When a thin film of fluchloralin on a Pyrex surface was irradiated for a 48-hr period, 52% of initial fluchloralin photolyzed(1). (14)C labeled fluchloralin was applied to dry thin layer soil plates and exposed to unfiltered solar radiation for 7 days in July(2); after the 7-day exposure, it was determined that 30.4% of the initial fluchloralin had photodegraded(2). Using irradiation in the environmental spectrum from a photoreactor, the quantum yield of fluchloralin in aqueous solution was determined to be 0.0041(3); the photodecomposition half-life was 29.2 min(3).

An estimated BCF value of 733 was calculated for fluchloralin(SRC), using an estimated log Kow of 5.07(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests the potential for bioconcentration in aquatic organisms is high(SRC).

3.55e+03 L/kg|The adsorption of fluchloralin was studied in 10 different soils all consisting of varying amounts of sand, clay, silt, and organic matter(1). Soil adsorption (Kd) coefficients ranged from 1.4-17.1 with a mean value of 8.1(1). Koc values calculated from these soils ranged from 150-550(1,SRC). According to a classification scheme(2), this range of Koc values suggest that fluchloralin has moderate to low mobility in soil(SRC).|... IS STRONGLY ADSORBED BY CLAY COLLOIDS & ORGANIC MATTER & THESE TWO CHARACTERISTICS INFLUENCE THE NECESSARY HERBICIDAL RATE REQUIRED.

... MODERATE VOLATILIZATION OCCURS.|The Henry's Law constant for fluchloralin is estimated as 1.5X10-5 atm-cu m/mole(SRC), derived from its experimental values for vapor pressure, 3X10-5 mm Hg at 20 °C(1), and water solubility, 0.9 mg/L at 20 °C(2). This Henry's Law constant indicates that fluchloralin is expected to volatilize from moist soil and water surfaces(3). 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 103 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 54 days(SRC). Volatilization from dry soil surfaces is not expected(SRC) based on the vapor pressure(1).|Laboratory studies were conducted to measure 3-hr vapor losses of dinitroaniline herbicides from various soils(1); from Lakeland sand at 7% soil moisture, vapor losses of fluchloralin were about 1, 2 and 11% at respective temperatures of 30, 40 and 50 °C(1); from Lakeland sand at 15.3% soil moisture, vapor losses of fluchloralin were about 0.5, 2 and 8.5% at respective temperatures of 30, 40 and 50 °C(1); from Littleton silt loam and Hagerstown clay loam at 50 °C and 25% soil moisture, the respective vapor losses were about 2.5 and 5%(1). In another soil volatilization study, volatilization losses of fluchloralin ranged from about 8 to 30% at 25 °C under dry conditions, field capacity or flooded conditions(2); at 4 °C, losses ranged from about 1-4%(2).

In a US monitoring survey of 6970 produce samples (fruits and vegetables) collected between 1989 and 1991, fluchloralin was detected (detection limit of 0.05 ppm) in only one sample(1); the concn in the sample (onions) was not reported(1).

Occupational exposure and general population exposure should be low or non-existent since fluchloralin is no longer produced or used in the US. In the past, fluchloralin was used as an herbicide and exposure to this compound was primarily by dermal contact in the field where it was applied. (SRC)

Little or no foliar absorption. Fluchloralin is used for soil incorporated applications. Translocation characteristics; root uptake and acropetal movement throughout the entire plant occurs.

Three structurallyrelated (14)C dinitroaniline herbicides including fluchloralin, were extensively metabolized in vitro by both normal and phenobarbital-induced rat liver microsomes. Identification of the metabolites in the ethyl acetate extracts indicated that aliphatic hydroxylation, N-dealkylation, reduction of a nitro group, and cyclization were the predominant metabolic routes in vitro. Of particular interest was the formation of a benzimidazole metabolite.|Soybean roots and shoots metabolized fluchloralin to at least 10 nonpolar metabolites, 6 polar metabolites, and some methanol soluble residue. TLC, GLC, and MS were used to identify metabolites: 1-(2-chloroethyl)2-ethyl-7-nitro-5-trifluoromethylbenzimidazole; alpha-alpha-alpha-trifluoro-N-(2-chloroethyl)-N-propyl-5-nitrotoluene- 3,4-diamine, obtained from excised leaves and roots; 2-chloromethyl-7-nitro-1-propyl-5-trifluoromethylbenzimidazole; and 2-amino-N-(2-chloroethyl)-6-nitro-N-propyl-4-trifluoromethylaniline.|Fluchloralin was extensively metabolized in vitro by normal and phenobarbital induced rat liver microsomes. Metabolites produced indicated that fluchloralin metabolism involved N-dealkylation, aliphatic hydroxylation, nitro reduction and cyclization. Analyses with TLC and GC-MS indicated the formation of 2,6-dinitro-N-(n-propan-3-ol)-alpha,alpha,alpha- trifluoro-p-toluidine and the corresponding N-(n-propan-2-ol) analog. N-dealkylation of fluchloralin gave the des-2-chloroethyl analog and di- dealkylated analogs. Other metabolites observed included 2-amino-6-nitro-alpha,alpha,alpha-trifluoro-p-toluidine, 5-nitro-7-trifluoromethylquinoxaline, and 2-ethyl-7-nitro-5-trifluoromethyl benzimidazole.

Skin decontamination. Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|Gastrointestinal decontamination. Ingestions of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if spontaneous diarrhea has not already commenced. Dehydration and electrolyte disturbances may be severe enough to require oral or intravenous fluids. ... If large amounts of herbicide have been ingested and the patient is seen within an hour of the ingestion, gastrointestinal decontamination should be considered ... If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol by mouth. /Other herbicides/|Intravenous fluids. If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. /Other herbicides/|Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides ... If the patient's condition deteriorates in spite of good supportive care, the operation of an alternative or additional toxicant should be suspected. /Other herbicides/|For more Antidote and Emergency Treatment (Complete) data for FLUCHLORALIN (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ May be mildly irritating. /Flurodinitrotoluidine/ herbicides do not uncouple oxidative phosphorylation or generate methemoglobin.|/GENOTOXICITY/ Cultured human lymphocytes were exposed to three different concentrations (2.5, 5.0 and 10.0 ug/mL) of fluchloralin for 24 and 48 hr to assess chromosomal aberrations. A significant dose-dependent increase of chromatid type aberration was observed in these cells. Multiple aberrations (MA) were scored at all concentrations after 48 hr treatment. To support these results ... /the/ micronucleus (MN) test /was performed/ using cytochalasin B to block cytokinesis. At lower concentrations (2.5 to 10.0 ug/mL) the frequency of MN induction was not significantly different. Higher concentrations of fluchloralin (20, 40 and 50 ug/mL) resulted in a significant dose dependent increase in number of micronucleated cells.|/SIGNS AND SYMPTOMS/ Symptomatology indicates overdosing may produce /CNS depression/ and other general CNS involvement.

Basalin

BAS 392-H-TECHNICAL, BAS 3921 H-3 LB/US GALLON, BAS 3923 H-5% GRANULE.|EMULSIFIABLE CONCENTRATE (4 LB/GALLON); EMULSIFIABLE CONCENTRATE 45% WT/WT.

Crops sensitive to fluchloralin are beets, sorghum, spinach and oats..|Controls smooth crabgrass, large crabgrass, barnyardgrass, giant foxtail, yellowfoxtail, goosegrass, japanese millet, junglerice, fall panicum, broadleaf signalgrass, seedling johnsongrass, texas panicum, pigweed, lambsquarters, common purslane, florida pusley, carpetweed and morningglory. Fluchloralin is selective in cotton, soybeans, peanuts, dry beans, snap beans, lima beans, peas & several vegetable crops.|Discontinued in 1985 by BASF

RESIDUES ARE DETECTED BY GC USING ELECTRON CAPTURE OR NITROGEN-SPECIFIC COULSON ELECTROLYTIC CONDUCTIVITY DETECTION. LIMIT OF SENSITIVITY FOR THE ANALYSIS OF RESIDUES IN WATER IS 1 PPB, SOIL IS 10 PPB, AND PLANT MATERIAL IS 10-50 PPB.|EPA Method 646.Determination of dinitro aromatic pesticides in wastewater by GC with an ECD. Under the prescribed conditions, fluchloralin has an estimated detection limit of 0.0005 ug/l as defined by EPA.|GLC determination of fluchloralin residues and its metabolite in cotton and soybean foliage and seed or grain and soil samples with 10% 3N hydrogen chloride in methanol. Sensitivity is 0.05 ppm. Recoveries obtained by EPA were 84 and 76% and 72 and 74% fluchloralin added to soybean samples at the 0.05 ppm and 0.1 ppm level respectively.|EPA Method 3540. Soxhlet Extraction. A solid sample is mixed with anhydrous sodium sulfate and extracted using an appropriate solvent in a Soxhlet extractor. The sample is then dried and concentrated using a Kuderna-Danish apparatus. This is a procedure for extracting nonvolatile and semivolatile organic compounds from solids such as soils, sludges, and waste.|For more Analytic Laboratory Methods (Complete) data for FLUCHLORALIN (6 total), please visit the HSDB record page.

Pharmaceuticals|HERBICIDES