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PROFLURALIN
CASRN: 26399-36-0
For other data, click on the Table of Contents
Human Health Effects:
Emergency Medical Treatment:
Emergency Medical Treatment:
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The following Overview, *** GENERAL OR UNKNOWN CHEMICAL ***, is relevant for this HSDB record chemical. |
| Life Support: |
o This overview assumes that basic life support measures
have been instituted.
|
| Clinical Effects: |
SUMMARY OF EXPOSURE
0.2.1.1 ACUTE EXPOSURE
o A SPECIFIC REVIEW on the clinical effects and treatment
of individuals exposed to this agent HAS NOT YET BEEN
PREPARED. The following pertains to the GENERAL
EVALUATION and TREATMENT of individuals exposed to
potentially toxic chemicals.
o GENERAL EVALUATION -
1. Exposed individuals should have a careful, thorough
medical history and physical examination performed,
looking for any abnormalities. Exposure to chemicals
with a strong odor often results in such nonspecific
symptoms as headache, dizziness, weakness, and nausea.
o IRRITATION -
1. Many chemicals cause irritation of the eyes, skin, and
respiratory tract. Respiratory tract irritation, if
severe, can progress to pulmonary edema, which may be
delayed in onset for up to 24 to 72 hours in some
cases.
2. Irritation or burns of the esophagus or
gastrointestinal tract are also possible if caustic or
irritant chemicals are ingested.
o HYPERSENSITIVITY -
1. A number of chemical agents produce an allergic
hypersensitivity dermatitis or asthma with
bronchospasm and wheezing with chronic exposure.
|
| Laboratory: |
o A number of chemicals produce abnormalities of the
hematopoietic system, liver, and kidneys. Monitoring
complete blood count, urinalysis, and liver and kidney
function tests is suggested for patients with significant
exposure.
o If respiratory tract irritation or respiratory depression
is evident, monitor arterial blood gases, chest x-ray, and
pulmonary function tests.
|
| Treatment Overview: |
SUMMARY EXPOSURE
o A specific review on the clinical effects and treatment
of individuals exposed to this agent has not yet been
prepared. The following pertains to the general
evaluation and treatment of individuals exposed to
potentially toxic chemicals.
o Move victims of inhalation exposure from the toxic
environment and administer 100% humidified supplemental
oxygen with assisted ventilation as required. Exposed
skin and eyes should be copiously flushed with water.
1. Rescuers must not enter areas with potential high
airborne concentrations of this agent without
SELF-CONTAINED BREATHING APPARATUS (SCBA) to avoid
becoming secondary victims.
o Measures to decrease absorption may be useful. The
decision to induce or not to induce emesis in ingestions
must be carefully considered. If the patient has any
signs of esophageal or gastrointestinal tract irritation
or burns, or has evidence of a decreased sensorium, a
depressed gag reflex, or impending shock, INDUCED EMESIS
SHOULD BE AVOIDED.
ORAL EXPOSURE
o GASTRIC LAVAGE
1. Significant esophageal or gastrointestinal tract
irritation or burns may occur following ingestion. The
possible benefit of early removal of some ingested
material by cautious gastric lavage must be weighed
against potential complications of bleeding or
perforation.
2. GASTRIC LAVAGE: Consider after ingestion of a
potentially life-threatening amount of poison if it can
be performed soon after ingestion (generally within 1
hour). Protect airway by placement in Trendelenburg
and left lateral decubitus position or by endotracheal
intubation. Control any seizures first.
a. CONTRAINDICATIONS: Loss of airway protective reflexes
or decreased level of consciousness in unintubated
patients; following ingestion of corrosives;
hydrocarbons (high aspiration potential); patients at
risk of hemorrhage or gastrointestinal perforation;
and trivial or non-toxic ingestion.
o ACTIVATED CHARCOAL
1. Activated charcoal binds most toxic agents and can
decrease their systemic absorption if administered soon
after ingestion. In general, metals and acids are
poorly bound and patients ingesting these materials
will not likely benefit from activated charcoal
administration.
a. Activated charcoal should not be given to patients
ingesting strong acidic or basic caustic chemicals.
Activated charcoal is also of unproven value in
patients ingesting irritant chemicals, where it may
obscure endoscopic findings when the procedure is
justified.
2. ACTIVATED CHARCOAL: Administer charcoal as slurry (240
mL water/30 g charcoal). Usual dose: 25 to 100 g in
adults/adolescents, 25 to 50 g in children (1 to 12
years), and 1 g/kg in infants less than 1 year old.
o DILUTION -
1. Immediate dilution with milk or water may be of benefit
in caustic or irritant chemical ingestions.
2. DILUTION: Following ingestion and/or prior to gastric
evacuation, immediately dilute with 4 to 8 ounces (120
to 240 mL) of milk or water (not to exceed 15 mL/kg in
a child).
o IRRITATION -
1. Observe patients with ingestion carefully for the
possible development of esophageal or gastrointestinal
tract irritation or burns. If signs or symptoms of
esophageal irritation or burns are present, consider
endoscopy to determine the extent of injury.
o OBSERVATION CRITERIA -
1. Carefully observe patients with ingestion exposure for
the development of any systemic signs or symptoms and
administer symptomatic treatment as necessary.
2. Patients symptomatic following exposure should be
observed in a controlled setting until all signs and
symptoms have fully resolved.
INHALATION EXPOSURE
o DECONTAMINATION -
1. INHALATION: Move patient to fresh air. Monitor for
respiratory distress. If cough or difficulty breathing
develops, evaluate for respiratory tract irritation,
bronchitis, or pneumonitis. Administer oxygen and
assist ventilation as required. Treat bronchospasm
with beta2 agonist and corticosteroid aerosols.
o IRRITATION -
1. Respiratory tract irritation, if severe, can progress
to pulmonary edema which may be delayed in onset up to
24 to 72 hours after exposure in some cases.
o PULMONARY EDEMA/NON-CARDIOGENIC -
1. PULMONARY EDEMA (NONCARDIOGENIC): Maintain ventilation
and oxygenation and evaluate with frequent arterial
blood gas or pulse oximetry monitoring. Early use of
PEEP and mechanical ventilation may be needed.
o BRONCHOSPASM -
1. If bronchospasm and wheezing occur, consider treatment
with inhaled sympathomimetic agents.
o OBSERVATION CRITERIA -
1. Carefully observe patients with inhalation exposure for
the development of any systemic signs or symptoms and
administer symptomatic treatment as necessary.
2. Patients symptomatic following exposure should be
observed in a controlled setting until all signs and
symptoms have fully resolved.
EYE EXPOSURE
o DECONTAMINATION: Irrigate exposed eyes with copious
amounts of tepid water for at least 15 minutes. If
irritation, pain, swelling, lacrimation, or photophobia
persist, the patient should be seen in a health care
facility.
DERMAL EXPOSURE
o DERMAL DECONTAMINATION -
1. DECONTAMINATION: Remove contaminated clothing and wash
exposed area thoroughly with soap and water. A
physician may need to examine the area if irritation
or pain persists.
o PESTICIDES -
1. DECONTAMINATION: Remove contaminated clothing and
jewelry. Wash the skin, including hair and nails,
vigorously; do repeated soap washings. Discard
contaminated clothing.
o IRRITATION -
1. Treat dermal irritation or burns with standard topical
therapy. Patients developing dermal hypersensitivity
reactions may require treatment with systemic or
topical corticosteroids or antihistamines.
o DERMAL ABSORPTION -
1. Some chemicals can produce systemic poisoning by
absorption through intact skin. Carefully observe
patients with dermal exposure for the development of
any systemic signs or symptoms and administer
symptomatic treatment as necessary.
|
| Range of Toxicity: |
o No specific range of toxicity can be established for the
broad field of chemicals in general.
|
Antidote and Emergency Treatment:
1. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FLUSH CONTAMINATED EYES
WITH COPIOUS AMT OF FRESH WATER FOR 15 MIN. 3. INGESTIONS OF SMALL AMT (LESS
THAN 10 MG/KG BODY WT) OCCURRING LESS THAN AN HR BEFORE TREATMENT, ARE PROBABLY
BEST TREATED BY: A. SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER. DOSE
FOR ADULTS & CHILDREN OVER 12 YR: 30 ML. DOSE FOR CHILDREN UNDER 12 YR:
15 ML. B. ACTIVATED CHARCOAL ADMIN.../PRC- 30 G IN 3-4 OZ OF WATER (CHILDREN),
100 G IN 8-10 OZ OF WATER (ADULTS)/. C. SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG
IN TAP WATER, AS A CATHARTIC. /PESTICIDES OF LOW OR MODERATE TOXICITY/
4. INGESTIONS OF LARGE AMT (MORE THAN 10 MG/KG) OCCURRING LESS THAN AN HR
BEFORE TREATMENT, SHOULD PROBABLY BE TREATED BY GASTRIC LAVAGE: A. INTUBATE
STOMACH & ASPIRATE CONTENTS. B. LAVAGE STOMACH WITH SLURRY OF ACTIVATED
CHARCOAL.../PRC- 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER
(ADULTS)/. LEAVE 30-50 G ACTIVATED CHARCOAL IN THE STOMACH BEFORE WITHDRAWING
TUBE. C. SODIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. /PESTICIDES
OF LOW OR MODERATE TOXICITY/
CAUTION: HYDROCARBONS (KEROSENE, PETROLEUM DISTILLATES) ARE INCL IN SOME FORMULATIONS...
INGESTION OF VERY LARGE AMT MAY CAUSE CNS DEPRESSION. IN THIS CASE, IPECAC IS
CONTRAINDICATED. ALSO, GASTRIC INTUBATION INCURS RISK OF...PNEUMONITIS. FOR
THIS REASON...(1) IF VICTIM IS UNCONSCIOUS OR OBTUNDED & FACILITIES ARE
AT HAND, INSERT AN ENDOTRACHEAL TUBE (CUFFED, IF AVAIL) PRIOR TO GASTRIC INTUBATION.
(2) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING INTUBATION & LAVAGE
(TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD).
KEEP VICTIM'S HEAD TURNED TO LEFT. (3) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE
TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. /PESTICIDES OF LOW OR MODERATE
TOXICITY/
5. INGESTIONS OCCURRING MORE THAN AN HR BEFORE TREATMENT ARE PROBABLY BEST
TREATED ONLY BY ACTIVATED CHARCOAL../PRC- 30 G IN 3-4 OZ WATER (CHILDREN), 100
G IN 8-10 OZ WATER (ADULTS)/ & SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG, AS
DESCRIBED ABOVE. 6. THERE IS NO SPECIFIC ANTIDOTE FOR THESE CHEMICALS. BECAUSE
MANIFESTATIONS OF TOXICITY DO OCCASIONALLY OCCUR IN PECULIARLY PREDISPOSED INDIVIDUALS,
MAINTAIN CONTACT WITH VICTIM FOR AT LEAST 72 HR SO THAT UNEXPECTED ADVERSE EFFECTS
CAN BE TREATED PROMPTLY. /PESTICIDES OF LOW OR MODERATE TOXICITY/
Animal Toxicity Studies:
Non-Human Toxicity Excerpts:
IT IS...TOXIC TO HONEY BEES.
THE INFLUENCE OF SGA-10832 ON RHIZOPODA, FLAGELLATA & INFUSORIA WAS STUDIED
IN THE UPPER 20-CM LAYER OF CHERNOZEM TYPE SOIL AT DIFFERENT DATES AFTER TREATMENT
IN EARLY MAY. WHEN APPLIED AT A RATE OF 250 CC/10 SQ M, IT HAD AN INHIBITORY
EFFECT ON THE RHIZOPODS AND FLAGELLATES, WHILE THE INFUSORIA POPULATION REMAINED
UNCHANGED.
THE EFFECT OF A PRE-EMERGENCE HERBICIDE ON THE GROWTH OF ROTTBOELLIA EXALTATA
WAS DETERMINED USING DIFFERENT CONCN OF PROFLURALIN. CONCN OF 5, 10, 25 AND
50 PPM INDUCED INHIBITION OF ROOT AND SHOOT GROWTH ACCOMPANIED BY SWELLING OF
ROOT TIPS AND COLEOPTILAR NODES. ABNORMAL ENLARGEMENT OF THE CELLS WAS APPARENT
IN ALL SWOLLEN TISSUES. MULTI-NUCLEARITY OF THE CELLS IN THE PERICYCLIC LAYER
& INCR IN THE NUMBER OF ROOT & LEAF PRIMORDIUM INITIALS WERE OBSERVED.
Non-Human Toxicity Values:
LD50 Rat oral about 10000 mg/kg
LD50 Rat percutaneous greater than 3170 mg/kg
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
PRESENT DATA INDICATE THAT MINUTE QUANTITIES OF POLAR METABOLITES ARE GENERATED
IN COTTON AND SOYBEANS.
...IN RAT-LIVER MICROSOMES...PROFLURALIN WAS METABOLIZED ANALOGOUSLY /TO TRIFLURALIN,
BY HYDROXYLATION OF THE PROPYL RESIDUE AND/OR N-DEALKYLATION/... THE BENZIMIDAZOLE
WAS A METABOLITE.
Profluralin was extensively metabolized in vitro by normal and phenobarbital-induced
rat liver microsomes. Metabolites produced indicated that profluralin metabolism
involved N-dealkylation, aliphatic hydroxylation, nitro reduction and cyclization.
Analyses ... 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 profluralin
gave the des-n-propyl and di-dealkylated analogs and 2-ethyl-7-nitro-5-trifluoromethyl
benzimidazole ... .
The metabolism of profluralin was studied in rats. Male Sprague-Dawley rats
were administered 1 g/kg or 600 mg/kg profluralin by stomach tube. Bulk urine
samples were collected from rats given 600 mg/kg profluralin for 2 weeks and
analyzed for metabolites using chromatographic methods fluorine-l9 nuclear magnetic
resonance spectroscopy and mass spectrometry. Urine samples were collected 4,
13, 56, or 72 hr after dosing from rats given 1 g/kg profluralin to study the
time course of metabolite excretion. At least 20 metabolites were detected in
the bulk urine samples from their nuclear magnetic resonance chemica1 shifts.
A didea1ky1ated monoreduced compound was the major metabolite. A hydroxylamine
derivative was the first and major profluralin metabolite observed during the
first 4 hr after dosing. 2-Diamino-4-(trifluoromethyl)-6-nitro-benzenamine was
the major metabolite at later times. Approximately 10 to 15 percent of the profluralin
dose was excreted during the first 72 hours after dosing. /It was/ concluded
that profluralin is metabolized by rats into many species that can be distinguished
on the basis of their fluorine-19 chemical shifts. Fluorine-19 nuclear magnetic
resonance spectroscopy is a feasib1e technique for detecting fluorine containing
species in biological fluids and monitorinq the time course of their appearance.
Absorption, Distribution & Excretion:
ROOTS OR SHOOTS OF OATS AND PEAS WERE EXPOSED TO VAPORS OF (14)C-LABELED PROFLURALIN.
THE HERBICIDE WAS ABSORBED BY ROOTS AND SHOOTS OF GERMINATING OATS AND PEAS.
SOME ROOT-SHOOT TRANSLOCATION WAS OBSERVED IN PEAS, BUT NO SHOOT-ROOT TRANSPORT
COULD BE DETECTED IN EITHER PEAS OR OATS. IN PEAS, (14)C FROM ROOT-ABSORBED
PROFLURALIN WAS DETECTED IN SHOOTS.
SORGHUM, BARNYARDGRASS, SOYBEAN, AND PALMER AMARANTH WERE TREATED WITH (14)C-LABELED
PROFLURALIN IN NUTRIENT SOLN FOR 24 HR @ 26 OR 38 DEG C. PROFLURALIN ACCUM IN
ROOTS TO A GREATER EXTENT AT 16 DEG, WHEREAS METAB WAS GREATEST AT 35 DEG. VERY
LITTLE PROFLURALIN WAS TRANSLOCATED TO THE TOPS OF PLANTS. THESE EFFECTS MAY
RELATE TO EXCESS TOXICITY OF PROFLURALIN AT 16 DEG IN SPECIES WHICH NORMALLY
EXHIBIT RESISTANCE TO THE HERBICIDES.
Mechanism of Action:
CGA-10832 (AT 1X10-6 MOLAR) INHIBITED CYCLIC PHOTOPHOSPHORYLATION OF ISOLATED
PEA CHLOROPLASTS AND DECR STATE-3 RESPIRATION OF BOTH ISOLATED BEAN HYPOCOTYLS
AND RAT LIVER MITOCHONDRIA.
CGA 10832 PARTIALLY INHIBITED THE PHOTOSYNTHESIS (MEASURED BY OXYGEN EVOLUTION)
OF SPINACH LEAF DISCS.
Interactions:
TOBACCO TISSUE CULTURES WERE USED IN A BIOASSAY SYSTEM FOR DETERMINING THE
EFFECT OF PROFLURALIN ON GROWTH. THE MOLAR CONCN REQUIRED TO INHIBIT FRESH WT
GAIN BY 50% (I50) WAS DETERMINED. EXOGENOUSLY APPLIED D-ALPHA-TOCOPHEROL ACETATE
AT 100 TIMES THE I50 CONCN DECR THE INHIBITION OF TISSUE GROWTH BY PROFLURALIN.
Pharmacology:
Interactions:
TOBACCO TISSUE CULTURES WERE USED IN A BIOASSAY SYSTEM FOR DETERMINING THE
EFFECT OF PROFLURALIN ON GROWTH. THE MOLAR CONCN REQUIRED TO INHIBIT FRESH WT
GAIN BY 50% (I50) WAS DETERMINED. EXOGENOUSLY APPLIED D-ALPHA-TOCOPHEROL ACETATE
AT 100 TIMES THE I50 CONCN DECR THE INHIBITION OF TISSUE GROWTH BY PROFLURALIN.
Environmental Fate & Exposure:
Environmental Fate/Exposure Summary:
Profluralin's production and former use as a selective pre-planting herbicide
has in the past resulted in its release to the environment through various herbicidal
applications. Profluralin has been detected in one groundwater well out of 86.
If released to the atmosphere, profluralin will exist in both the vapor and
particulate phases. Vapor-phase profluralin will react with photochemically
produced hydroxyl radicals with an estimated half-life of 167 hours. Particulate-phase
profluralin may be physically removed from the air by wet and dry deposition.
If released to water, profluralin will adsorb to suspended solids and sediment
in the water. Profluralin may volatilize from water surfaces with estimated
half-lives for a model pond of 150-178 days. Hydrolysis is expected to be very
slow for profluralin in water. Bioconcentration in aquatic organisms will be
an important fate process for profluralin. If released to soil, profluralin
will be immobile. Volatilization from moist soil and photodegradation of profluralin
may be important from soil surfaces. Profluralin is persistent in soil and may
carryover to the following growing season. Biodegradation of profluralin can
occur in both aerobic and anaerobic conditions but may not be important in comparison
to volatility and chemical decomposition. (SRC)
Artificial Pollution Sources:
Profluralin's former production and use as a selective pre-planting herbicide(1)
resulted in its release to the environment through various herbicidal applications(SRC).
Environmental Fate:
TERRESTRIAL FATE: Experimental Koc values of 8600(2) and 10,232(3) indicate
that profluralin will have no mobility in soil(SRC) according to a suggested
classification scheme(1). Volatilization of profluralin may be important from
moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.15X10-4
atm-cu m/mole(SRC) calculated from experimental values of water solubility(5)
and vapor pressure(6). Vapor losses of profluralin from moist Lakeland soil
at 50 deg C approached 25 percent after 3 hours(7). A number of studies have
examined the persistence (which includes degradation, chemical decomposition,
and volatilization) of profluralin in soils(8-11). The following results were
obtained: In Crowley silt loam used for soybeans and rice (at 0.84 kg/ha) profluralin
had a half-life of approximately 11 weeks(8); at 1.5 kg/ha, 20 percent of the
profluralin applied remained after one year on sandy loam, heavy clay, and silty
clay(9); Profluralin remained at 90.6, 92, 72, and 84 percent of the initial
concentration 48, 115, 187, and 248 days after application on a Plano silt loam
at 5 deg C(10); Profluralin had half-lives of 60 and 124 days, on Bosket sandy
loam and Sharkey clay, respectively(11). Photodegradation may also contribute
to the loss of profluralin from soil surfaces(12-15). Biodegradation of profluralin
can occur in both aerobic and anaerobic conditions but may not be important
in comparison to volatility and chemical decomposition(8).
AQUATIC FATE: Based on a recommended classification scheme(1), experimental
Koc values of 8600(2) and 10232(3) indicate that profluralin may adsorb to suspended
solids and sediment(SRC) in the water. Profluralin may volatilize from water
surfaces based on an estimated Henry's Law constant of 3.15X10-4 atm-cu m/mole(SRC),
calculated from its experimental values for vapor pressure, 6.9X10-5 mm Hg at
20 deg C(6), and water solubility, 0.1 mg/L at 20 deg C(7). Taking adsorption
to sediment and suspended solids into account, the half-life for a model pond
has been estimated to be 150-178 days(5,SRC). An estimated BCF value of 10,200(6,SRC),
from an experimental log Kow(4), suggests that bioconcentration of profluralin
in aquatic organisms will be very high(SRC) according to a classification scheme(9).
At 20 deg C, hydrolysis half-lives for profluralin were: 29 days at a pH of
13, 150 days at a pH of 1, and 1200 days in deionized water(10). Biodegradation
of profluralin can occur in both aerobic and anaerobic conditions but may not
be important in comparison to volatility and chemical decomposition(11).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental
vapor pressure of 6.9X10-5 mm Hg at 20 deg C(2) indicates that profluralin will
exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase
profluralin 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 17 hours(3,SRC). Particulate-phase profluralin may be physically
removed from the air by wet and dry deposition(SRC).
Environmental Biodegradation:
INVESTIGATIONS WERE CARRIED OUT ON THE DEGRADATION OF PROFLURALIN BY SOIL
MICROORGANISMS. THE MOST ACTIVE DEGRADERS WERE TENTATIVELY IDENTIFIED AS ARTHROBACTER
SIMPLEX, CELLULOMONAS FLAVIGENUM, AND MICROBACTERIUM FLAVUM. STEPS IN THE DEGRADATION
PATHWAY INVOLVE DEALKYLATION OF THE AMINO NITROGEN AND REDN OF AT LEAST ONE
OF THE NITRO GROUPS. CO-METABOLIC PROCESSES WERE APPARENTLY INVOLVED, &
EXOGENOUS CARBON AND NITROGEN WERE REQUIRED FOR DEGRADATION.
SAMPLES OF (14)C-LABELED PROFLURALIN WERE INCUBATED WITH SEWAGE AEROBICALLY
AND UNDER DISCONTINUOUS ANAEROBIOSIS FOR 88 DAYS AND FRESH SEWAGE WAS ADDED
AT INTERVALS. YIELD OF RECOVERED PRODUCTS REACHED 87%. NONE OF THE RADIOACTIVITY
FROM THE HERBICIDE ENTERED THE NUCLEOSIDE POOL OF THE SEWAGE MICROFLORA.THE
LACK OF INCORPORATION OF SUBSTRATE C INTO CELLS AND THE ALMOST STOICHIOMETRIC
CONVERSION OF THE SUBSTRATE TO ORGANIC PROD INDICATE THAT MEMBERS OF THE MICROBIAL
COMMUNITY WERE COMETABOLIZING THE TEST CMPD.
CGA 10832 WAS METABOLIZED BY ASPERGILLUS FUMIGATUS, FUSARIUM OXYSPORUM, AND
PAECILOMYCES SPECIES FUNGI.
Profluralin has a half-life of 110 days in soil(1). Profluralin metabolites
were recovered at yields of 87 and 23 percent in aerobic and discontinuous anaerobic
conditions, respectively, in sewage(2). Cometabolism appears to be involved
in the microbial degradation of profluralin since detection of profluralin's
isolates only occurred when the cultures were provided with additional sources
of nitrogen and carbon(3). Two pathways have been proposed for the degradation
of dinitroaniline herbicides in soil: under aerobic conditions, the herbicides
are first dealkylated and the nitro groups are reduced; under anaerobic conditions,
the process is reversed(4).
Environmental Abiotic Degradation:
PROFLURALIN IS SUBJECT TO LOSS FROM THE SOIL BY VAPORIZATION AND PHOTODEGRADATION.
RATE OF DISSIPATION IS MOST RAPID WHEN PROFLURALIN IS APPLIED TO A WET OR DAMP
SOIL SURFACE. A HOT, PACKED, OR SMOOTH SOIL SURFACE, WIND, OR STRONG SUNLIGHT
MAY ALSO STIMULATE THE RATE OF PROFLURALIN DISAPPEARANCE.
The rate constant for the vapor-phase reaction of profluralin with photochemically
produced hydroxyl radicals has been estimated as 2.28X10-11 cu cm/molecule-sec
at 25 deg C(SRC) using a structure estimation method(1,SRC). This corresponds
to an atmospheric half-life of about 17 hours at an atmospheric concentration
of 5X10+5 hydroxyl radicals per cu cm(1,SRC). At 20 deg C, hydrolysis half-lives
for profluralin were: 29 days @ pH 13, 150 days @ pH 1, and 1200 days in deionized
water(2). The half-life for the photodecomposition of profluralin was 44 minutes
using UV light (310-410 nm)(3). After exposure to sunlight on soil thin layer
plates for 7 days, profluralin did not degrade to any appreciable extent(4).
Profluralin, in soil, degraded 47.6 percent in another study when exposed to
sunlight after 7 days(5). Using UV light of 385-395 nm, 94 and 53 percent of
the initial profluralin remained on a dry Taloka silt loam thin-layer surface
at 5 and 45 deg C, respectively, after 24 hours(6). Abiotic reduction of profluralin
in homogeneous solutions of quinone redox couples (used to imitate the redox-labile
functional groups in natural organic matter) occurred as a second order reaction
with a rate constant of 79.0 L/min mol(7).
Environmental Bioconcentration:
An estimated BCF value of 10,200 was calculated for profluralin(SRC), using
an experimental log Kow of 5.58(1) and a recommended regression-derived equation(2).
According to a classification scheme, this BCF value suggests that bioconcentration
in aquatic organisms will be very high(3).
Soil Adsorption/Mobility:
DUE TO THE STRONG SOIL ADSORPTION CHARACTERISTICS AND APPLICATION METHODS
(SOIL INCORPORATION), THE POSSIBILITY OF HAZARDOUS CONDITIONS TO FISH RESULTING
FROM RECOMMENDED USAGE IS NIL.
PROFLURALIN IS STRONGLY ADSORBED TO ORGANIC MATTER AND CLAY. THEREFORE, IT
IS NOT LEACHED THROUGH THE SOIL OR CARRIED ACROSS THE SOIL SURFACE AS RUNOFF
UNLESS SOIL MOVEMENT OR EROSION TAKES PLACE. EVEN WHEN MINOR EROSION OCCURS,
RELATIVELY LITTLE PROFLURALIN WILL BE CARRIED FROM THE TREATED AREA IF IT HAS
BEEN MECHANICALLY INCORPORATED INTO THE SOIL.
The Koc of profluralin is estimated as approximately 25,800(SRC), using an
experimental log Kow of 5.58(1) and a regression-derived equation(2,SRC). The
Koc for profluralin has also been experimentally determined to be 8,600(4) and
10,232(5). According to a recommended classification scheme(3), these Koc values
suggest that profluralin is immobile in soil(SRC). Profluralin was adsorbed
66 to 74 percent by organic matter and 9 to 10 percent by montmorillonite after
4 hours of equilibration in an experimental study(6). Desorption solutions of
water and CaCl2 (1 normal) desorbed profluralin 12.8 and 11.8 percent, respectively,
from organic matter and 93.3 and 69 percent, respectively, from montmorillonite(6).
Volatilization from Water/Soil:
The Henry's Law constant for profluralin is estimated as 3.15X10-4 atm-cu
m/mole(SRC) from its experimental values for vapor pressure, 6.9x10-5 mm Hg
at 20 deg C(1), and water solubility, 0.1 mg/l at 20 deg C(2). This value indicates
that profluralin will volatilize from water surfaces(3,SRC). Taking adsorption
to sediment and suspended solids into account, the estimated half-life for a
model pond is 150-178 days(5,SRC). Profluralin's high Henry's Law constant(1,2,SRC)
indicates that volatilization from moist soil may occur(SRC).
Environmental Water Concentrations:
GROUNDWATER: Of 86 wells in Georgia that were sampled for profluralin during
1984-1991, only one well contained profluralin (concentration = 20 ug/l)(1).
Sediment/Soil Concentrations:
PROFLURALIN WAS INCUBATED IN AN ETOWAH SILT LOAM SOIL @ 0.5 PPM AT 73 AND
95 DEG F FOR 7-17 DAYS USING 3 PH LEVELS (5.3, 6.4 AND 7.5). MAX DISAPPEARANCE
OF PROFLURALIN OCCURRED AT A PH OF 6.4.
RESIDUES RESULTING FROM 1.7 KG CGA10832/HA IN SEQUATCHIE LOAM SOIL 120 DAYS
AFTER HERBICIDE APPLICATION WERE 0.54-0.86 PPM.
THE AVERAGE PERSISTENCE AT RECOMMENDED RATES OF PROFLURALIN IN SOILS SUCH
AS: SANDY LOAM, FINE SANDY LOAM, SILT LOAM, SILTY CLAY LOAM, CLAY LOAM IS DEGRADED
IN SIX MO 70%, 74%, 74%, 75% AND 82% RESPECTIVELY.
Food Survey Values:
Profluralin was analyzed for but not detected (detection limit = 0.050 ppm)
on 6970 produce samples(1).
Environmental Standards & Regulations:
FIFRA Requirements:
Removed (means the info was taken out of the source).
Chemical/Physical Properties:
Molecular Formula:
C14-H16-F3-N3-04
Molecular Weight:
347.33
Color/Form:
YELLOW-ORANGE CRYSTALS OR LIQUID
Odor:
NO APPRECIABLE ODOR
Melting Point:
33-36 DEG C
Corrosivity:
NON-CORROSIVE
Octanol/Water Partition Coefficient:
Log Kow = 5.58
Solubilities:
O.1 PPM IN WATER AT 27 DEG C; GREATER THAN 1 G/G OF ACETONE
GREATER THAN 1 G/G OF XYLENE, ETHANOL, ULTRACENE, SINCLAIR 90, N-HEXANE, AROMATIC
AND ALIPHATIC HYDROCARBONS, KETONES; GREATER THAN 1 G/3 G OF LOWER ALCOHOLS
READILY SOL IN MOST ORG SOLVENTS
Water solubility = 0.1 mg/L at 20 deg C.
Spectral Properties:
Intense mass spectral peaks: 318 m/z (100%), 330 m/z (54%), 69 m/z (28%),
264 m/z (21%)
Vapor Pressure:
6.9X10-5 MM HG @ 20 DEG C
Other Chemical/Physical Properties:
DECOMPOSITION TEMP APPROX 180 DEG C
SPECIFIC GRAVITY: 1.45 @ 25 DEG C /TECHNICAL/
Chemical Safety & Handling:
Stability/Shelf Life:
SHELF-LIFE OF AT LEAST 3 TO 5 YR
DECOMP BY UV IRRADIATION
Storage Conditions:
STORE...IN DRY PLACE...MINIMUM STORAGE TEMP (-20 DEG F)...
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary
landfill) disposal practices are subject to significant revision. Prior to implementing
land disposal of waste residue (including waste sludge), consult with environmental
regulatory agencies for guidance on acceptable disposal practices.
Occupational Exposure Standards:
Manufacturing/Use Information:
Major Uses:
SELECTIVE PRE-PLANTING HERBICIDE (FORMER USE)
Manufacturers:
Ciba-Geigy Corp, Hq, Saw Mill River Road,
Ardsley. NY 10502, (914)478-3131. Agricultural Div., P.O. Box 18300, Swing Road
at I-40, Greensboro, NC 27419, (919)292-7100. Production
site: McIntosh, Ala 36553.
Methods of Manufacturing:
IT CAN BE MADE BY REACTING 4-CHLORO-3,5-DINITRO BENZOTRIFLUORIDE WITH N-CYCLOPROPYLMETHYL-N-N-PROPYLAMINE.
General Manufacturing Information:
PROFLURALIN SHOULD BE MECHANICALLY INCORPORATED FOR MAXIMUM BIOLOGICAL ACTIVITY.
SUITABLE INCORPORATION EQUIPMENT INCLUDES PTO-DRIVEN CULTIVATORS, HOES, TILLERS,
DOUBLE DISK, ROLLING CULTIVATORS, AND BED CONDITIONERS. APPLICATION AND INCORPORATION
CAN BE PREPLANTING, POST PLANTING, OR AT LAYBY. RATES: SAND, LOAMY SAND, SANDY
LOAM (LIGHT) 0.5 TO 0.75 LB/ACRE; LOAM, SILT LOAM, SILT (MEDIUM) 0.75 TO 1.50
LB/ACRE; CLAY LOAM, SILTY CLAY, CLAY (HEAVY) 1.0 TO 1.5 LB/ACRE. DO NOT USE
ON MUCK AND PEAT.
IN THE GREENHOUSE, SEEDING IN SOIL TREATED WITH PROFLURALIN (1-2 LB/ACRE)
INCR THE SUSCEPTIBILITY OF SOYBEAN TO ROOT ROT, CAUSED BY FUSARIUM OXYSPORUM.
IT DECR ROOT DEVELOPMENT AND CAUSED HYPOCOTYL SWELLING, THUS PREDISPOSING THE
PLANTS TO FUNGAL INFESTATION.
COTTON ROOT PRUNING OCCURRED IN PLOTS TREATED WITH PROFLURALIN (1.5 AND 3.0
LB/ACRE) AT TEMP OF 17-24 DEG C USING OVERHEAD IRRIGATION.
Discontinued by Ciba-Geigy Corp.
Formulations/Preparations:
WATER AT 10 TO 40 GAL PER ACRE IS THE CARRIER FOR THE 4 LB/GAL EMULSIFIABLE
CONCENTRATE.
Laboratory Methods:
Analytic Laboratory Methods:
...BY GLC WITH INTERNAL STANDARD.
PROFLURALIN WAS SEPARATED FROM OTHER PESTICIDES BY CAPILLARY GAS CHROMATOGRAPHY.
DETECTION LIMITS OF 50 PG WERE ATTAINED.
RESIDUES MAY BE DETERMINED, AFTER COLUMN CHROMATOGRAPHIC CLEAN-UP, BY GLC
WITH MICROCOULOMETRIC DETECTION.
PROFLURALIN WAS DETERMINED IN INDUSTRIAL OR MUNICIPAL WASTEWATER BY GAS CHROMATOGRAPHY.
THE EXTRACTION FROM SEVERAL FIELD SOILS OF PROFLURALIN APPLIED AT LEAST 6
MO PREVIOUSLY WAS COMPARED USING SIX SOLVENT SYSTEMS. THE RESIDUES WERE QUANTIFIED
USING GAS CHROMATOGRAPHY TECHNIQUES.
Special References:
Synonyms and Identifiers:
Synonyms:
B 4576
**PEER REVIEWED**
BENZENAMINE, N-(CYCLOPROPYLMETHYL)-2,6-DINITRO-N-PROPYL-4-(TRIFLUOROMETHYL)-
**PEER REVIEWED**
CGA 10832
**PEER REVIEWED**
N-CYCLOPROPYLMETHYL-2,6-DINITRO-N-PROPYL-4-TRIFLUOROMETHYLANILINE
**PEER REVIEWED**
N-(CYCLOPROPYLMETHYL)-2,6-DINITRO-N-PROPYL-4-(TRIFLUOROMETHYL)BENZENAMINE
**PEER REVIEWED**
N-CYCLOPROPYLMETHYL-N-N-PROPYL-4-TRIFLUOROMETHYL-2,6-DINITROANILINE
**PEER REVIEWED**
N-(CYCLOPROPYLMETHYL)-ALPHA,ALPHA,ALPHA-TRIFLUORO-2,6-DINITRO-N-PROPYL-P-
TOLUIDINE
**PEER REVIEWED**
ER5461
**PEER REVIEWED**
GA-10832
**PEER REVIEWED**
PREGARD
**PEER REVIEWED**
SGA 10832
**PEER REVIEWED**
TOLBAN
**PEER REVIEWED**
P-TOLUIDINE, N-(CYCLOPROPYLMETHYL)-2,6-DINITRO-N-PROPYL-ALPHA,ALPHA,ALPHA-TRIFLUORO
**PEER REVIEWED**
P-TOLUIDINE, N-(CYCLOPROPYLMETHYL)-ALPHA,ALPHA,ALPHA-TRIFLUORO-2,6-DINITRO-N-PROPYL-
**PEER REVIEWED**
Formulations/Preparations:
WATER AT 10 TO 40 GAL PER ACRE IS THE CARRIER FOR THE 4 LB/GAL EMULSIFIABLE
CONCENTRATE.
RTECS Number:
NIOSH/XU5785000
Administrative Information:
Hazardous Substances Databank Number: 3923
Last Revision Date: 20010809
Last Review Date: Reviewed by SRP on 5/16/1996
Update History:
Complete Update on 08/09/2001, 1 field added/edited/deleted.
Complete Update on 05/15/2001, 1 field added/edited/deleted.
Complete Update on 06/12/2000, 1 field added/edited/deleted.
Complete Update on 02/08/2000, 1 field added/edited/deleted.
Complete Update on 02/02/2000, 1 field added/edited/deleted.
Complete Update on 09/21/1999, 1 field added/edited/deleted.
Complete Update on 08/27/1999, 1 field added/edited/deleted.
Complete Update on 06/02/1998, 1 field added/edited/deleted.
Complete Update on 03/08/1998, 1 field added/edited/deleted.
Complete Update on 10/31/1997, 1 field added/edited/deleted.
Complete Update on 01/28/1997, 1 field added/edited/deleted.
Complete Update on 08/07/1996, 37 fields added/edited/deleted.
Field Update on 05/13/1996, 1 field added/edited/deleted.
Field Update on 01/27/1996, 1 field added/edited/deleted.
Complete Update on 12/30/1994, 1 field added/edited/deleted.
Complete Update on 03/25/1994, 1 field added/edited/deleted.
Field update on 12/31/1992, 1 field added/edited/deleted.
Complete Update on 01/28/1992, 1 field added/edited/deleted.
Complete Update on 03/06/1990, 1 field added/edited/deleted.
Field update on 03/06/1990, 1 field added/edited/deleted.
Complete Update on 12/19/1989, 1 field added/edited/deleted.
Complete Update on 10/03/1986