FLUORIDE ACTION NETWORK PESTICIDE PROJECT
Return to FAN's Pesticide Homepage
Return to Trifluralin Index Page
Trifluralin. TOXNET profile from Hazardous Substances Data Base.
See for Updates: http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB
TRIFLURALIN
CASRN: 1582-09-8
For other data, click on the Table of Contents
Human Health Effects:
Evidence for Carcinogenicity:
Evaluation: There is inadequate evidence in humans for the carcinogenicity
of trifluralin. There is limited evidence in experimental animals for the carcinogenicity
of technical grade trifluralin. Overall evaluation: Trifluralin is not classifiable
as to its carcinogenicity to humans (Group 3).
CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Classification
is based on the induction of urinary tract tumors (renal pelvis carcinomas and
urinary bladder papillomas) and thyroid
tumors (adenomas/carcinomas combined) in
one animal species (F344 rats) in one study. Trifluralin
is structurally similar to ethalfluralin, a carcinogen in the rat.
HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.
Human Toxicity Excerpts:
SINCE 1969, 16 EPISODES OF TRIFLURALIN POISONING HAVE BEEN REPORTED. THERE
HAVE BEEN NO FATALITIES, & ONLY 1 CASE REQUIRED HOSPITALIZATION. 10 OF 16
CASES INVOLVED SYMPTOMS THAT APPEARED TO BE RELATED TO THE SOLVENT, RATHER THAN
TRIFLURALIN ITSELF.
SUMMARY TOXICITY STATEMENT /ACUTE/= MODERATE VIA ORAL ROUTE. MODERATE= MAY
CAUSE REVERSIBLE OR IRREVERSIBLE CHANGES TO EXPOSED TISSUE, NOT PERMANENT INJURY
OR DEATH; CAN CAUSE CONSIDERABLE DISCOMFORT.
Skin, Eye and Respiratory Irritations:
Cause eye irritation. May cause skin sensitization reactions in certain individuals.
Probable Routes of Human Exposure:
... NO DISCERNIBLE HAZARDS FROM TECHNICAL TRIFLURALIN; SOLVENT SYSTEM IN EMULSIFIABLE
CONCENTRATES MAY BE IRRITATING TO SKIN & EYES. PERSONNEL WHO FORMULATE OR
APPLY TRIFLURALIN HAVE NOT EXPERIENCED DISCOMFORT OR UNTOWARD EFFECTS.
DISCOVERY OF THE VOLATILE NITROSAMINE, N-NITROSODI-N-PROPYLAMINE AS CONTAMINANT
OF TRIFLURALIN, PROMPTED INVESTIGATION INTO POSSIBLE EXPOSURE OF FIELD WORKERS.
SAMPLING & ANALYTICAL TECHNIQUES USED DEMONSTRATED A LOW LEVEL OF EXPOSURE
POTENTIAL.
Occupational exposure to trifluralin may occur by inhalation or dermal contact
during its production, formulation, or application as a herbicide(SRC). Dermal
exposure to trifluralin by farmworkers may also occur long after initial exposure
as this compound has been found to be adsorbed to clothing even after numerous
washings(1,2). Trifluralin residues ranging from 1.6 to 11.9 ng/sq cm were found
on cotton overalls which were worn for four seasons and washed after every day
of use(1). The general population may be exposed to trifluralin by dermal and
inhalation exposure from lawn products and by ingestion of contaminated agricultural
products(3) or the ingestion of fish caught in contaminated waters(4).
Emergency Medical Treatment:
Emergency Medical Treatment:
| EMT Copyright Disclaimer: |
| Portions of the POISINDEX(R) database are provided here for
general reference. THE COMPLETE POISINDEX(R) DATABASE, AVAILABLE FROM MICROMEDEX,
SHOULD BE CONSULTED FOR ASSISTANCE IN THE DIAGNOSIS OR TREATMENT OF SPECIFIC
CASES. Copyright 1974-1998 Micromedex, Inc. Denver, Colorado. All Rights
Reserved. Any duplication, replication or redistribution of all or part
of the POISINDEX(R) database is a violation of Micromedex' copyrights and
is strictly prohibited.
The following Overview, *** TRIFLURALIN ***, 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 Trifluralin is irritating to the eyes, and produces
mild skin irritation after prolonged exposure.
Administration of lethal doses to animals results in
CNS and respiratory depression. Adverse effects in
humans have not been described.
HEENT
0.2.4.1 ACUTE EXPOSURE
o IRRITATION - Lacrimation, photophobia, redness, and
purulent conjunctivitis lasting 5 to 7 days were noted
in rabbits after instillation of trifluralin into the
conjunctival sac.
RESPIRATORY
0.2.6.1 ACUTE EXPOSURE
o RESPIRATORY DEPRESSION - Administration of lethal doses
intragastrically to animals resulted in shallow,
infrequent, and interrupted respirations within 20 to
25 minutes, with death from respiratory arrest within 3
hours to 2 days.
NEUROLOGIC
0.2.7.1 ACUTE EXPOSURE
o CNS DEPRESSION - Administration of lethal doses
intragastrically to animals produced flaccidity,
adynamia, and tremor.
HEMATOLOGIC
0.2.13.1 ACUTE EXPOSURE
o Unspecified adverse hematologic effects were noted in
rats given chronic doses.
DERMATOLOGIC
0.2.14.1 ACUTE EXPOSURE
o HYPEREMIA - Single applications of 5% trifluralin to
the skin was not irritating to rats. Successive daily
applications for 5 days produced mild hyperemia lasting
2 days.
REPRODUCTIVE HAZARDS
o In one mouse study, trifluralin administration was
associated with various skeletal anomalies in the
offspring.
CARCINOGENICITY
0.2.21.2 HUMAN OVERVIEW
o CARCINOGENICITY - Chronic trifluralin produced
hepatocellular carcinomas in animals.
GENOTOXICITY
o MUTAGENICITY - Trifluralin is strongly mutagenic in
plants, producing a 3 to 4 times increase in spontaneous
mitoses and chromosomal aberrations.
|
| Laboratory: |
o Monitor complete blood count in patients with significant
exposures.
|
| Treatment Overview: |
SUMMARY EXPOSURE
o There are no specific antidotes. Trifluralin is
irritating to eyes and skin, and potentially to mucous
membranes, and may rapidly produce CNS and respiratory
depression after large ingestions. Dilution followed by
gastric lavage and activated charcoal may be preferable
to ipecac-induced emesis.
ORAL EXPOSURE
o Because of the potential for the rapid development of
CNS and respiratory depression, ipecac-induced emesis is
not recommended.
o 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 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.
1. 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: 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 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.
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 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.
|
| Range of Toxicity: |
o Minimum lethal human exposure is unknown. |
Antidote and Emergency Treatment:
Skin decontamination: Skin contamination should he 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.
Gastrointestinal decontamination: Ingestion 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 diarrhea has not
already commenced. Dehydration and electrolyte may be severe enough to require
oral or intravenous fluids. There are no specific antidotes for poisoning by
these herbicides. In the case of suicidal ingestions, particularly, the possibility
must always be kept in mind that multiple toxic substances may have been swallowed.
If large amounts of herbicide have been ingested and the patient is seen 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
mouth.
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.
Animal Toxicity Studies:
Evidence for Carcinogenicity:
Evaluation: There is inadequate evidence in humans for the carcinogenicity
of trifluralin. There is limited evidence in experimental animals for the carcinogenicity
of technical grade trifluralin. Overall evaluation: Trifluralin is not classifiable
as to its carcinogenicity to humans (Group 3).
CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Classification
is based on the induction of urinary tract tumors (renal pelvis carcinomas and
urinary bladder papillomas) and thyroid
tumors (adenomas/carcinomas combined) in one animal species (F344 rats) in one
study. Trifluralin is structurally similar to ethalfluralin, a carcinogen in
the rat. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.
Non-Human Toxicity Excerpts:
RABBITS EXPOSED TO 500 MG OF TECHNICAL TRIFLURALIN IN STD DRAIZE SKIN IRRITATION
STUDY HAD SCORE OF 0, INDICATING NO DERMAL IRRITATION. TECHNICAL TRIFLURALIN
ALSO CAUSED NO DAMAGE WHEN TESTED IN RABBIT EYES.
IN 10-DAY STUDY OF CATTLE, SHEEP, & CHICKENS ORALLY TREATED WITH TRIFLURALIN
... NO-ADVERSE-EFFECT DOSAGE WAS 100 MG/KG/DAY ... .
HARLAN RATS (6 MALES & 6 FEMALES IN EACH GROUP) WERE FED TECHNICAL TRIFLURALIN
AT 20, 200, 2000, & 20,000 PPM IN DIET FOR 2 YR. AT HIGHEST DOSAGE LEVEL,
RATS SHOWED SIGNIFICANT GROWTH RETARDATION & BILE DUCT PROLIFERATION &
SURVIVED MAX OF 460 DAYS. IN ALL OTHER GROUPS ... NO SIGNIFICANT DIFFERENCES
BETWEEN TREATED ANIMALS & CONTROLS ... .
TECHNICAL GRADE TRIFLURALIN DID NOT INDUCE POINT MUTATIONS IN SALMONELLA/MAMMALIAN
MICROSOME ASSAY OR STIMULATION OF UNSCHEDULED DNA SYNTHESIS, BUT INDUCED AN
INCR OF MITOTOC CROSSING-OVER IN ASPERGILLUS NUDULANS. A PURIFIED SAMPLE SHOWED
NO GENETIC ACTIVITY WHEN TESTED IN THE SAME GENETIC SYSTEM.
IN TERATOLOGY STUDIES THERE WAS NO EFFECT WITH: RATS AT 2000 MG/KG DIET; DOGS
AT 1000 MG/KG DIET; RABBITS AT 1000 MG/KG BODY WT DAILY.
... 8 MONGREL DOGS WERE GIVEN DAILY ORAL DOSES IN CAPSULES OVER 2-YR PERIOD.
1 MALE & 1 FEMALE IN EACH GROUP WERE GIVEN 2.5 MG/KG, 5 MG/KG, & 25
MG/KG. 2 FEMALES WERE GIVEN 10 MG/KG. THERE WERE NO ADVERSE EFFECTS @ ANY DOSAGE.
IN 3-YR STUDY, PUREBRED BEAGLES WERE GIVEN TRIFLURALIN ORALLY @ 10 & 25
MG/KG. EACH TREATMENT GROUP INCL 2 ANIMALS OF EACH SEX, & CONTROL GROUP
WAS ESTABLISHED WITH 3 ANIMALS OF EACH SEX. AT 25 MG/KG, INCR LIVER:BODY-WEIGHT
RATIO WAS OBSERVED. THEREFORE, NO-ADVERSE-EFFECT DOSAGE WAS CONSIDERED TO BE
10 MG/KG.
CHICKENS, WHICH ARE SENSITIVE TO CATARACTOGENIC PROPERTIES OF COMPOUNDS, WERE
EXPOSED TO TRIFLURALIN. THERE WAS NO EFFECT IN TRIFLURALIN-TREATED CHICKENS
...
ORAL TOXICITY /FEMALE MALLARD DUCKS & MALE PHEASANTS 3-4 MO OF AGE/ ACUTE
SYMPTOMS: VERY MILD ATAXIA ONLY.
OCCURRENCE OF VERTEBRAL DYSPLASIA IN BROWN TROUT SALMO TRUTTA WAS ATTRIBUTED
TO PREEMERGENCE HERBICIDE, ACTIVE INGREDIENT TRIFLURALIN, WHICH WAS ACCIDENTALLY
DISCHARGED INTO STREAM.
OF 19 HERBICIDES INCUBATED AT 1 TO 100 PPM FOR 7 DAYS WITH EARTHWORMS IN SAND
SOIL SAMPLES, ONLY 100 PPM TRIFLURALIN CAUSED MORTALITY, KILLING ALL WORMS.
The dinitroanilines /including trifluralin/ are considered to be moderately
persistent herbicides in the soil. They are generally considered to have a very
low degree of toxicity to mammals and are degraded in the environment to products
without significant adverse effects on organisms.
Examples of dinitroanilines include ... trifluralin ..., the oral LD50 value
/for rats/ ... is >10,000 mg/kg. Not only /does this/ cmpd have a low acute
toxicity in mammals, but rats and dogs showed no ill effect when fed a dietary
level of 1,000 ppm for 2 years.
TRIFLURALIN AFFECTS PHYSIOLOGICAL GROWTH PROCESSES ASSOC WITH SEED GERMINATION.
Trifluralin (2,6-dinitro-N,N-di-N-propyl-alpha,alpha,alpha-trifluoro-p-toluidine)
is the active ingredient in the herbicide TREFLAN. The potential developmental
toxicity of trifluralin was evaluated in rats and rabbits. Pregnant rats and
rabbits were dosed once daily by gavage on gestation days 6-15 and 6-18, respectively.
Doses for rats were 0, 100, 225, 475, and 1000 mg/kg; doses for rabbits were
0, 100, 225, 500 and 800 mg/kg. Cesarean sections performed on rats and rabbits
on gestation days 20 and 28, respectively. In rats, maternal toxicity was indicated
at the 475 and 1000 mg/kg dose levels by depression of body weight gain and
food consumption. Fetal viability and morphology were not adversely affected
at any dose level. Developmental toxicity was indicated at the 1000 mg/kg dose
level by depressed fetal weight. The no observed effect levels for maternal
and developmental toxicity in the rat were 225 and 475 mg/kg, respectively.
The A/D /adult to developmental/ ratio in rats was less than 1. In rabbits,
maternal toxicity was indicated at the 225, 500, and 800 mg/kg dose levels by
abortions and/or deaths in conjunction with depression of body weight gain and
food consumption. Developmental toxicity was indicated at the 500 and 800 mg/kg
dose levels by depressed fetal viability and weight. Fetal morphology was not
adversely affected at any dose level. The no observed efect levels for maternal
and developmental toxicity in the rabbit were 100 and 225 mg/kg, respectively.
The A/D /adult to developmental/ ratio in rabbits was less than 1. Based on
these data, trifluralin did not exhibit selective toxicity toward the developing
conceptus.
National Toxicology Program Studies:
A bioassay for possible carcinogenicity of technical grade trifluralin was
conducted using Osborne-Mendel rats and B6C3F1 mice. Analysis of the technical
product established the presence of 84 to 88 ppm dipropylnitrosamine. The product
was admin in the feed, at either of two concn, to groups of 50 male and 50 female
animals of each species. 50 animals of each sex were placed on test as controls
for the rat bioassay, while 20 of each sex were utilized as controls on the
mouse study. The time weighted avg high and low dietary concentrations of trifluralin
were, respectively, 8,000 and 4,125 ppm for male rats, 7,917 and 4,125 ppm for
female rats, 3,744 and 2,000 ppm for male mice, and 5,192 and 2,740 ppm for
female mice. After a 78 wk treatment period, there was an additional observation
period of 33 wk for rats and 12 wk for mice. For female mice the association
between incr dosage and elevated incidence of hepatocellular carcinomas was
significant (0/20, 12/47, and 21/44 of the control, low dose, and high dose,
respectively) as was the relationship between dose and incidence of alveolar/bronchiolar
adenomas. Significance of incidence for both types of tumors was supported by
tests for significance at each dose level. Squamous cell carcinomas of the stomach
were observed in dosed female mice, but not in controls. Although incidences
of these tumors were not statistically significant, they are unusual lesions
in B6C3F1 mice and are considered treatment related. Neoplasms observed in treated
rats were types that have occurred spontaneously in this strain and were apparently
unrelated to trifluralin treatment. Evaluation of the results of this bioassay,
technical grade trifluralin is a carcinogen in female B6C3F1 mice, being associated
with incr incidences of hepatocellular carcinomas, alveolar/bronchiolar adenomas
and squamous cell carcinomas of the forestomach. Sufficient evidence was not
provided for the carcinogenicity or tumorigenicity of trifluralin in male B6C3F1
mice or Osborne-Mendel rats. Evaluation of the results of this bioassay indicates
that technical grade trifluralin is a carcinogen in female B6C3F1 mice, being
associated in these animals with an elevated incidence of hepatocellular carcinomas,
alveolar/bronchiolar adenomas and squamous cell carcinomas of the forestomach.
Sufficient evidence was not provided for the carcinogenicity or tumorigenicity
of trifluralin in male B6C3F1 mice or in Osborne-Mendel rats of either sex.
Levels of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male
Mice: Negative; Female Mice: Positive.
Non-Human Toxicity Values:
LD50 Rat oral >10,000 mg/kg
LD50 Mouse oral 500 mg/kg
LD50 Rabbit oral >2000 mg/kg
LD50 Dog oral >2000 mg/kg
LD50 Chicken oral >2000 mg/kg
LD50 Mouse acute oral 5,000 mg/kg
LD50 Rat oral 1930 mg/kg
LD50 Rat skin >5,000 mg/kg
LD50 Mouse oral 3197 mg/kg
LD50 Dog oral >2000 mg/kg
LD50 Rabbit oral >2000 mg/kg
LD50 Rat oral 0, 100, 225, 475, and 1000 mg/kg
LD50 Rabbit oral 0, 100, 225, 500 and 800 mg/kg.
Ecotoxicity Values:
THE 24 HR MEDIAN LETHAL CONCN (LC50) OF TRIFLURALIN FOR MOSQUITOFISH &
JUVENILE CRAWFISH WERE 28 & 13 PPM. THE 96 HR LC50 WAS 12 PPM.
LC50 SIMOCEPHALUS 900 UG/L/48 HR @ 15 DEG C (95% CONFIDENCE LIMIT 651-1,245
UG/L), FIRST INSTAR /TECHNICAL MATERIAL, 95.9%/ STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 DAPHNIA MAGNA 560 UG/L/48 HR @ 21 DEG C (95% CONFIDENCE LIMIT 320-1000
UG/L), FIRST INSTAR /TECHNICAL MATERIAL, 95.9%/ STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY Ff
30-35 MG/L.
LC50 DAPHNIA PULEX 625 UG/L/48 HR @ 15 DEG C (95% CONFIDENCE LIMIT 446-876
UG/L), FIRST INSTAR /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 GAMMARUS FASCIATUS 2,200 UG/L/96 HR @ 21 DEG C (95% CONFIDENCE LIMIT
1,400-3,400 UG/L), MATURE /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT
AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY
OF 30-35 MG/L.
LC50 PTERONARCYS 2,800 UG/L/96 HR @ 15 DEG C (95% CONFIDENCE LIMIT 2,100-3,700
UG/L), SECOND YR CLASS /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT
AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY
OF 30-35 MG/L.
LC50 RAINBOW TROUT 41 UG/L/96 HR @ 12 DEG C (95% CONFIDENCE LIMIT 26-62 UG/L),
WT 0.8 G /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5,
WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
LC50 FATHEAD MINNOW 105 UG/L/96 HR @ 18 DEG C (95% CONFIDENCE LIMIT 83-134
UG/L), WT 0.8 G /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 CHANNEL CATFISH 2,200 UG/L/96 HR @ 22 DEG C (95% CONFIDENCE LIMIT 1,420-3,410
UG/L), WT 0.8 G /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 BLUEGILL 58 UG/L/96 HR @ 22 DEG C (95% CONFIDENCE LIMIT 47-70 UG/L),
WT 0.8 G /TECHNICAL MATERIAL, 95.9%/. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5,
WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
LC50 LARGEMOUTH BASS 75 UG/L/96 HR @ 18 DEG C (95% CONFIDENCE LIMIT 65-87
UG/L), WT 0.7 G /EMULISIFIABLE CONCENTRATE, 46%/. STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 GOLDFISH 145 UG/L/96 HR @ 18 DEG C (95% CONFIDENCE LIMIT 108-195 UG/L),
WT 1.0 G /EMULISIFIABLE CONCENTRATE, 46%/. STATIC BIOASSAY WITHOUT AERATION,
PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF
30-35 MG/L.
LC50 Channel catfish 417 ug/l/96 hr /Conditions of bioassay not specified/
LC50 Bluegill 0.019 ppm/48 hr /Conditions of bioassay not specified/
LC50 Rainbow trout 0.011 ppm/48 hr /Conditions of bioassay not specified/
LC50 Gammarus lacustris 2200 ug/l/96 hr /Conditions of bioassay not specified/
LC50 Gammarus fasciatus 1000 ug/l/96 hr /Conditions of bioassay not specified/
LC50 Daphnia magna 560 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Daphnia pulex 240 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Simocephalus serrulatus 450 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Cypridopsis vidua 250 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Asellus brevicaudus 200 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Palaemonetes kodiakensis 1200 ug/l/48 hr /Conditions of bioassay not
specified/
LC50 Orconectes nais 50,000 ug/l/48 hr /Conditions of bioassay not specified/
LC50 Pteronarcys californica 3000 ug/l/96 hr /Conditions of bioassay not specified/
LC50 Cyprinodon variegatus 190 ug/l/96 hr /Conditions of bioassay not specified/
LC50 Coturnix oral > 5,000 ppm (95% confidence interval)
LC50 Rainbow trout young 10-40 ug/l/96 hr and young bluegill sunfish 20-90
ug/l/96 hr; bluegill sunfish 19 ppb for 48 hr and rainbow trout 11 ppb for 48
hr.
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
MAJOR METABOLITES /FOUND IN URINE & FECES OF TREATED RUMINANTS/ WERE UNIDENTIFIED
POLAR COMPD, BUT N',N'-DIPROPYL-3-NITRO-5-TRIFLUOROMETHYL-ORTHO-PHENYLENEDIAMINE
& N(4)N(4)-DIPROPYL-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE-3,4,5-TRIAMINE WERE
ALSO FORMED.
TRIFLURALIN IS DEALKYLATED IN RUMEN /OF DAIRY ANIMALS/, LOSING 1 OR BOTH PROPYL
GROUPS; NITRO GROUPS ARE REDUCED TO 1 OR 2 AMINO GROUPS. 2 TYPES OF REACTIONS
OCCUR SIMULTANEOUSLY, LEADING TO A TRIFLUOROMETHYLTRIAMINOBENZENE.
METAB IN VITRO BY RAT LIVER MICROSOMES INDICATES ALIPHATIC HYDROXYLATION,
N-DEALKYLATION, REDN OF A NITRO GROUP, & CYCLIZATION TO BE MAJOR METABOLIC
ROUTES. A BENZIMIDAZOLE METABOLITE WAS FORMED.
The predominant metabolic pathways appear to be hydroxylation of alkyl groups
or N-dealkylation. To a lesser extent, a cyclized compound, benzimidazole, and
the reduction product of a nitro group, an amine, are also included in the pathways.
...
Absorption, Distribution & Excretion:
APPROX 80% OF INGESTED CMPD WAS EXCRETED IN FECES, REMAINDER IN URINE /OF
RATS & DOGS STUDIED/.
SALMON PARR SALMO SALAR WERE SUBJECTED TO HIGH INITIAL CONCN OF TRIFLURALIN
& THEN MAINTAINED IN CLEAR WATER FOR 12 MO. SOME WERE REMOVED AT PRESELECTED
INTERVALS FOR EXAM BY X-RAY & CHEM ANALYSIS. HALF-LIFE OF TRIFLURALIN IN
SALMON PARR WAS 40.5 DAYS.
Interactions:
MICE WERE FED TRIFLURALIN AT 1000, 1500 & 2000 PPM IN DIET FOR 12 OR 14
WEEKS. TUMORS WERE INDUCED BY ADMIN 8 MG OF BENZO(A)PYRENE ORALLY AT TWO TIME
PERIODS. INHIBITION OF TUMORIGENESIS IN LUNG & FORESTOMACH BY TRIFLURALIN
WAS OBSERVED WHEN IT WAS FED IN DIET 1 WK BEFORE OR 1 DAY FOLLOWING EXPOSURE
TO BENZO(A)PYRENE.
Pharmacology:
Interactions:
MICE WERE FED TRIFLURALIN AT 1000, 1500 & 2000 PPM IN DIET FOR 12 OR 14
WEEKS. TUMORS WERE INDUCED BY ADMIN 8 MG OF BENZO(A)PYRENE ORALLY AT TWO TIME
PERIODS. INHIBITION OF TUMORIGENESIS IN LUNG & FORESTOMACH BY TRIFLURALIN
WAS OBSERVED WHEN IT WAS FED IN DIET 1 WK BEFORE OR 1 DAY FOLLOWING EXPOSURE
TO BENZO(A)PYRENE.
Environmental Fate & Exposure:
Environmental Fate/Exposure Summary:
Trifluralin's use as a herbicide has resulted in its direct release to the
environment. If released to air, a vapor pressure of 4.58X10-5 mm Hg at 25 deg
C indicates trifluralin will exist in both the vapor and particulate phases
in the ambient atmosphere. Vapor-phase trifluralin will be degraded in the atmosphere
by reaction with photochemically produced hydroxyl radicals; the half-life for
this reaction in the air is estimated to be 16 hours. Direct photolysis is expected
to be an important environmental fate process based upon the observed half-life
for trifluralin in July sunlight which ranged from 25-60 minutes. Particulate-phase
trifluralin will be removed from the atmosphere by wet and dry deposition. If
released to soil, trifluralin is expected to have moderate to no mobility in
soils based on Koc values in the range of 397 to 16,851 measured in soils. Volatilization
from moist soil surfaces may be an important fate process based upon an experimental
Henry's Law constant of 1.03X10-4 atm-cu m/mole. Trifluralin was volatilized
16%, 28% and 40% in dry, moist and flooded soils over a 32 day incubation period.
Biodegradation is expected to be an important environmental fate process in
the environment. Trifluralin was degraded with half-lives of 189, 202, and 116
days in sandy loam, clay loam, and loam soils, respectively, when incubated
aerobically in the dark at 22 deg C for 364 days. If released into water, trifluralin
is expected to adsorb to suspended solids and sediment based upon its Koc values.
Volatilization from water surfaces may be an important environmental fate process
based upon this compound's experimental Henry's Law constant. Volatilization
half-lives for a model river and model lake are 0.5 days and 12 days, respectively.
Photolysis in sunlit surface waters may be an important environmental fate process
for this compound, based upon a direct photolysis half-life of 22 minutes in
near surface water, latitude 40 deg N in the summer. Trifluralin is stable to
hydrolysis. Experimental BCF values ranging from 1,689 to 9,586 suggest the
potential for bioconcentration in aquatic organisms is very high. Occupational
exposure to trifluralin may occur through inhalation of dust particles and dermal
contact with this compound at workplaces where trifluralin is produced or used.
Monitoring data indicate that the general population may be exposed to trifluralin
via ingestion of contaminated food. (SRC)
Probable Routes of Human Exposure:
... NO DISCERNIBLE HAZARDS FROM TECHNICAL TRIFLURALIN; SOLVENT SYSTEM IN EMULSIFIABLE
CONCENTRATES MAY BE IRRITATING TO SKIN & EYES. PERSONNEL WHO FORMULATE OR
APPLY TRIFLURALIN HAVE NOT EXPERIENCED DISCOMFORT OR UNTOWARD EFFECTS.
DISCOVERY OF THE VOLATILE NITROSAMINE, N-NITROSODI-N-PROPYLAMINE AS CONTAMINANT
OF TRIFLURALIN, PROMPTED INVESTIGATION INTO POSSIBLE EXPOSURE OF FIELD WORKERS.
SAMPLING & ANALYTICAL TECHNIQUES USED DEMONSTRATED A LOW LEVEL OF EXPOSURE
POTENTIAL.
Occupational exposure to trifluralin may occur by inhalation or dermal contact
during its production, formulation, or application as a herbicide(SRC). Dermal
exposure to trifluralin by farmworkers may also occur long after initial exposure
as this compound has been found to be adsorbed to clothing even after numerous
washings(1,2). Trifluralin residues ranging from 1.6 to 11.9 ng/sq cm were found
on cotton overalls which were worn for four seasons and washed after every day
of use(1). The general population may be exposed to trifluralin by dermal and
inhalation exposure from lawn products and by ingestion of contaminated agricultural
products(3) or the ingestion of fish caught in contaminated waters(4).
Artificial Pollution Sources:
Trifluralin's use as a herbicide(1) has resulted in its direct release to
the environment(SRC).
Environmental Fate:
TRIFLURALIN WAS MORE PERSISTENT IN SOIL (PH 6.56) THAN METRIBUZIN. HALF-LIFE
OF TRIFLURALIN WAS 38 DAYS FOR 670 G/HA & 61 DAYS FOR 1100 G/HA.
TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values
ranging from 397 to 16,851(2-8) indicate that trifluralin is expected to have
moderate to no mobility in soil(SRC). Volatilization of trifluralin from moist
soil surfaces may be an important fate process(SRC) given a Henry's Law constant
of 1.03X10-4 atm-cu m/mole(9). Trifluralin is known to rapidly volatilize from
both moist and dry soils to the atmosphere(10-13), although the volatilization
rate is greater for moist soils(14). Trifluralin was volatilized 16%, 28% and
40% in dry, moist and flooded soils over a 32 day incubation period(10). The
persistence of trifluralin in soil has been estimated at 6 months(16) and >40
weeks(15). Its persistence is less in southern climates than in northern ones(16).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from
397 to 16,851(2-8) indicate trifluralin is expected to adsorb to suspended solids
and sediment. Volatilization from water surfaces may be expected(9) based upon
experimental data(10) and a Henry's Law constant of 1.03X10-4 atm-cu m/mole(12),
although its strong adsorption to sediment and suspended organic matter may
attenuate the rate of this process(SRC). Using this Henry's Law constant and
an estimation method(9), volatilization half-lives for a model river and model
lake are 0.5 days and 12 days, respectively, when adsorption is ignored(SRC).
Trifluralin is not expected to hydrolyze in water(11). According to a classification
scheme(13), experimental BCF factors ranging from 1,689 to 9,586(14-17) suggest
the potential for bioconcentration in aquatic organisms is very high. The experimental
half-life for the direct photolysis of trifluralin in near surface water, latitude
40 deg N in the summer is 22 min(18).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile
organic compounds in the atmosphere(1), trifluralin, which has an experimental
vapor pressure of 4.58X10-5 mm Hg(2) at 25 deg C, will exist in both the vapor
and particulate phases in the ambient atmosphere. Vapor-phase trifluralin 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 16
hours(SRC), calculated from its rate constant of 24X10-12 cu cm/molecule-sec
at 25 deg C(SRC), determined using a structure estimation method(3). Particulate-phase
trifluralin may be removed from the air by wet and dry deposition(SRC). If released
to the atmosphere, trifluralin is expected to undergo rapid photolytic degradation;
the observed half-life for trifluralin in July sunlight ranged from 25-60 min(4).
In the presence of ozone, the rate of this reaction increases(5,6).
Environmental Biodegradation:
AEROBIC: Trifluralin biodegrades faster in anaerobic soils than in aerobic
soils(1). Trifluralin degraded with half-lives of 189, 202, and 116 days in
sandy loam, clay loam, and loam soils, respectively, when incubated aerobically
in the dark at 22 deg C for 364 days(2). Seven degradates of trifluralin have
been identified(2): alpha-alpha-alpha-trifluoro-2,6,-dinitro-N-propyl-p-toluidine;
alpha-alpha-alpha-trifluoro-5-nitro-4-propyl-toluene-3,4-diamine; 2-ethyle-7-nitro-1-propyl-5-(trifluoromethyl)benzimidazole-3-oxide;
2-ethyl-7-nitro-1-propyl-5-(trifluoromethyl) benzimidazole; 2-ethyl-7-nitro-5-(trifluoromethyl)benzimidazole;
alpha-alpha-alpha-trifluoro-2,6-dinitro-p-cresol; 2,2'-azoybis(alpha-alpha-alpha-trifluoro-6-nitro-N-propyl-p-toluidine(2).
These degradates were identified in test samples at maximum concns (% applied
radioactivity) of 2.8-4.6%, 1.5-2.1%, 0.1-0.3%, 0.5-1.0%, 2.1-2.6%, 0.1-2.7%,
and 0.8-3.0%, respectively(2). During the testing period of about one year,
trifluralin parent declined to less than 25% of applied radioactivity in all
soils(2). At the same time volatile and unextractable residues increased to
22% and about 45% of applied radioactivity(2). In another laboratory study,
the estimated half-life for the biodegradation of 1,000 ppm trifluralin in soil
was 405 days under aerobic conditions(3). Trifluralin, which was added to soil
obtained from a pesticide disposal site, did not biodegrade in 157 days under
aerobic conditions(4). Aerobic biodegradation of trifluralin proceeds through
an initial dealkylation followed by reduction of the nitro groups(5). The trifluoromethyl
group of trifluralin appears to remain intact in all major metabolites and is
eventually oxidized to the carboxylic acid(6). In a 14-day environmental chamber
study with a 14 hr photoperiod, degradation of 10 ppm trifluralin, present as
a mixture with metolachlor and atrazine, was shown to occur in non-vegetated
soil (47% degradation) but not to the extent of the Kochia scoparia rhizosphere
soil (70% degradation), suggesting that the rhizosphere of certain plant species
may facilitate microbial degradation(7).
Trifluralin at an initial concn of 100 ug/l underwent 49% removal when incubated
with primary sewage effluent under aerobic conditions; under anaerobic conditions
it underwent 91% removal during the same time period(1). Incubation of radiolabled
trifluralin with sediment samples under aerobic conditions resulted in a concn
reduction equal to 1/4 its original value after 10 days; the microbial community
was not found to adapt to trifluralin(2). The concn of trifluralin in shake
flask tests containing either natural water or a sediment water slurry were
found to decrease; the rate of decrease was less in sterilized flasks(3).
ANAEROBIC: Trifluralin biodegrades faster in anaerobic soils than in aerobic
soils(1). Trifluralin degraded with half-lives of 22-59 days in sandy loam,
loam, and clay loam soils incubated anaerobically in the dark at 22 deg C for
60 days following an aerobic incubation period of 30 days(2). In another laboratory
study, the estimated half-life for the biodegradation of 1,000 ppm trifluralin
in soil was 211 days under anaerobic conditions(3). Degradation under anaerobic
conditions initiates with nitro group reduction followed by dealkylation(4).
The major degradates identified were(2): alpha-alpha-alpha-trifluoro-5-nitro-N4,N4-dipropyl-toluene-3,4-diamine
(which reached a maximum concn of 5.4% and 13.2% of the applied radioactivity
in sandy loam soil and clay loam soil, respectivily, at Day 60 following flooding,
and 11.6% in the loam soil at Day 30 following flooding); 7-amino-2-ethyl-1-propyl-5-(trifluoromethyl)benzimidazole
(which reached 7.3% in sandy loam soil and 8.3% in loam and clay loam soils
at Day 60 following flooding); alpha-alpha-alpha-trifluoro-N4-N4-dipropyltoluene-3,4,5-triamine
(which reached 0.3% in sandy loam soil, 4.1% in loam soil, and 2.6% in clay
loam soil).
Environmental Abiotic Degradation:
The rate constant for the vapor-phase reaction of trifluralin with photochemically-produced
hydroxyl radicals has been estimated as 24X10-12 cu cm/molecule-sec at 25 deg
C(SRC) using a structure estimation method(1). This corresponds to an atmospheric
half-life of about 16 hours at an atmospheric concn of 5X10+5 hydroxyl radicals
per cu cm(1). Trifluralin is stable to hydrolysis(2).
Trifluralin underwent approx 10-15% loss when soil TLC plates incorporated
with the pesticide were exposed to the July sun for 6 days(1). Photodecomposition
of trifluralin in water leads to the formation of highly polar products via
N-dealkylation, nitro reduction and cyclization(2). Photolysis of water suspensions
of trifluralin under summer sunlight leads to the formation of mono and di-dealkylated
products, the corresponding benzimidazole and its N-oxide and the corresponding
phenol(3). In both laboratory and field gas-phase photolysis studies the same
products were produced(4-5). The half-life for the gas-phase photolysis of trifluralin
in the laboratory was 1 hour(6). The observed half-life for trifluralin when
irradiated by July sunlight ranged from 25-60 min(7). Trifluralin was found
to photodegrade to 50% of applied concn after 30 min irradiation to light of
wavelengths above 290 nm(8). Vapor-phase photolysis rates for trifluralin were
determined by sunlight irradiation; half-lives were found to range from 19 to
74 minutes. Simultaneous irradiation of methanolic solutions produced half-lives
of 17 to 25 min(9). Sunlight photolysis of trifluralin adsorbed to soil TLC
plate resulted in 18.4% removal in 7 days(10), although in the field it is not
believed that direct photolysis on the soil surface can compete with volatilization(11,12).
The rate of the gas-phase photolysis of trifluralin was found to increase in
the presence of ozone(13). The experimental half-life for the direct photolysis
of trifluralin in near surface water, latitude 40 deg N in the summer is 22
min(14). No change in the loss rate of trifluralin from soil was observed with
changing pH, indicating that pH dependent hydrolysis was not occurring(15).
Environmental Bioconcentration:
Fish bioconcentration factors estimated from field data were: sauger (Stizostedion
canadense), 5,421, shorthead redhorse (Moxostoma macrolepidolum), 2,832, and
golden redhorse (M. erthrurum), 1,689, and an experimental value of 3,261 for
fathead minnows (Pimephales promelas)(1). An experimental fish bioconcentration
factor of 4,570, species not stated, has been reported for trifluralin(2). The
bioconcentration factor for trifluralin in topmouth gudgeon (Pseudorasbora parva)
has been reported as 3,162(3). Mean bioconcentration factors accumulated in
bluegill sunfish exposed to 0.0059 ppm trifluralin ranged from 2,041 to 9,586(4).
According to a classification scheme(3), these BCF values suggest the potential
for bioconcentration in aquatic organisms is very high(SRC).
Soil Adsorption/Mobility:
Koc values of trifluralin have been experimentally determined to range from
397 to 16,851(1-7). According to a classification scheme(8), this range of Koc
values suggests trifluralin is expected to be moderately mobile to immobile
in soil. An experimental soil adsorption coefficient of 30,550 was determined
for trifluralin using Georgia pond sediment(9). Trifluralin was immobile in
soil TLC experiments using 14 different soils that ranged from sandy loam to
silty clay(10). In a laboratory screening study, trifluralin did not leach past
30 cm in 100 days(11-12). It was estimated that it would take 1580 yrs for trifluralin
to leach through soil to a depth of 3 m(12). Trifluralin was detected at 86%
of 28 agrochemical dealership sites in Iowa at a max concn of 14,200 ug/l(13).
Volatilization from Water/Soil:
The Henry's Law constant for trifluralin is 1.0X10-4 atm-cu m/mole(1). This
Henry's Law constant indicates that trifluralin 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)(3)
is estimated as 12 hours if adsorption is neglected(SRC). The volatilization
half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of
0.5 m/sec)(3) is estimated as 12 days if adsorption is neglected(SRC). The volatilization
from a model pond is about 8 yrs when adsorption is considered(4). Trifluralin's
Henry's Law constant(1) indicates that volatilization from moist soil surfaces
may occur(SRC). In a laboratory study, trifluralin underwent 24% volatilization
loss from a Lakeland soil in 3 hours; the rate of volatilization increased with
increasing soil moisture(5).Volatilization losses for trifluralin amounted to
approx 16% after 32 days in dry soil, approx 28% loss in moist soil and 40%
loss in flooded soil(6). In an ecosystem model mimicking a Northern prairie
wetland, trifluralin underwent approx 15% loss due to volatilization in 42 days(7).
In a laboratory study, trifluralin underwent 5% evaporative losses in 10 days
when incorporated to 10 cm depth in soil samples(8). The measured rate for volatilization
of trifluralin from nonadsorbent sand was 3 kg/ha/day(9).
Environmental Water Concentrations:
TRIFLURALIN WAS DETECTED IN FINISHED WATER IN US ...
GROUNDWATER: Trifluralin was detected in well water samples at a concn of
41 ug/l in 1 out of 179 wells from farms in an agricultural area in Ontario,
Canada, 1984-86(1,2). Trifluralin has been qualitatively detected in groundwater
samples in 4 states(3). It was detected in 1 of 1443 wells monitored in NE,
at a concn of 0.42 ppb(4). In a survey of U.S. groundwater quality, trifluralin
was detected in samples from KS, MD, MS, and NE as a result of normal use at
a mean and maximum concn of 2.20 ppb and 0.40 ppb, it was detected in ND as
a result of a point source contamination at 0.03 ppb and in KS from unknown
origin at a maximum and mean concn of 5.40 ppb and 3.09 ppb(5). Trifluralin
was detected in 3 groundwater samples collected from a small residential community
in South-Central Connecticut, the average detected concn was 0.04 ug/l(6). Trifluralin
was detected in 1 of 62 lake and river/stream sites sampled from 1989 to 1991
in a 4 county region of Arkansas at a maximum concn of 1.3 ug/l(7). Trifluralin
was detected in groundwater samples at 65% of 28 agrochemical dealership sites
in Iowa at a max concn of 58 ug/l(8).
SURFACE WATER: The concn of trifluralin in the Ochre and Turtle River, Canada,
1984, ranged from <0.6 to 3.3 ug/cu m and <0.5 to 5.2 ug/cu m(1). Water
samples taken from the Wabash River, IN, 1974, 8 km downstream from a pesticide
manufacturing facility contained 874 parts/per trillion trifluralin(2). It was
detected in Mississippi River water samples obtained 20 miles below Memphis,
TN, 1984, at a concn of 19 ng/l(3). Trifluralin has been detected in water from
Lake Erie and Lake Michigan watersheds(4). Its concn in the Wabash River, 1975,
ranged from 3.12 ug/l to 548 ug/l <1 mile from a pesticide manufacturing
facility(5). The concn of trifluralin in the Shell Creek, NE, 1988, after a
spring storm event ranged from trace to 0.5 ug/l(6). Trifluralin was detected
in 3 of 69 samples of natural waters from various regions of Greece, at concns
ranging from <0.005 to 0.01 ug/l(7). Trifluralin was detected in seawater,
ice and fog condensate samples taken from the Bering and Chukchi Seas during
the summer of 1993(8). Trifluralin concns ranged from <0.34 to 1150 pg/l
in seawater and ice samples while fog condensate concns ranged from <0.1
to <0.3 ng/l. Trifluralin was detected in air and surface water samples at
different elevations in California's Sequoia National Park during the summer
of 1996; trifluralin concn ranges detected for air and surface waters were 0.03
to 0.64 ng/cu m and non-detectable to 108.12 ng/l, respectively(9).
DRINKING WATER: Trifluralin was qualitatively detected in raw and finished
drinking water obtained from the Llobregat River, Barcelona, Spain(1).
RAIN/SNOW: The concn of trifluralin in "brown snow", snow contaminated by
a long range transport event, 1988, was 764 pg/l(1). Trifluralin was detected
in winter-spring rain/snow precipitation from Sequoia National Park and Lake
Tahoe Basin at concns ranging from 0.5 to 2 ng/l(2).
Effluent Concentrations:
The concn of trifluralin in wastewater samples from a pesticide manufacturer
in Barcelona, Spain, 1984, was 2 ppm(1). The estimated total discharges of trifluralin
into the Ochre and Turtle Rivers, Canada, 1984, from the surrounding watershed
are 119 and 37 g/yr(2).
Sediment/Soil Concentrations:
SOIL: Trifluralin was detected in soil samples from the corn belt states IL,
IA, MN, MO, and OH, 1970, at concns of 0.01-0.08 ppm, 0.02-0.06 ppm, 0.09-0.33
ppm, 0.03 ppm and 0.08 ppm, respectively(1). Trifluralin was detected in 52
of 1533 soil samples from 37 states during the Natl Soils Monitoring Program,
FY 1972, at 0.01-1.29 ppm, mean concn <0.01 ppm(2). During FY 1973, it was
found in 81 of 1483 sites at 0.01-1.86 ppm, mean concn 0.01 ppm(3) and FY 1970
it was found in 8 of 178 sites, 0.01-0.09 ppm mean concn <0.01 ppm(4). Residues
of trifluralin in soil samples from a pesticide disposal pit in CA, 1985, ranged
from <10-1104 ppm(5). Trifluralin was detected in and around 20 Illinois
retail agrichemical facilities that were flooded in 1993 at median on and off-site
concns of 0.71 mg/kg and 0.04 mg/kg, respectively(6). Trifluralin was detected
at 86% of 28 agrochemical dealership sites in Iowa at a max concn of 14,200
ug/l(7).
Atmospheric Concentrations:
SOURCE DOMINATED: Trifluralin was found in 5 of 56 air samples 275 m from
a formulation plant in TN at a mean concn of 10.2 ng/cu m (range 0-30.3 ng/cu
m)(1).
SUBURBAN/RURAL: Trifluralin was detected in 3 of 11 air samples taken from
Pekin, IL, 1980, at concns ranging from 1.3 to 5.0 ng/cu m(1). In a survey of
14 U.S. states, trifluralin was not detected in 787 samples taken in 1970, 7.9%
of 667 samples in 1971 (mean concn 0.2 ng/cu m), and 4.59% of 1025 samples in
1972 (mean concn 0.1 ng/cu m)(2).
Food Survey Values:
IN ANNUAL MARKET BASKET SURVEYS CONDUCTED BY FOOD AND DRUG ADMIN, TRIFLURALIN
RESIDUES HAVE NEVER BEEN DETECTED...
Trifluralin was qualitatively detected in domestic and imported agricultural
commodities in the FDA's pesticide residue monitoring program, FY 83-86(1).
The FDA found residues of trifluralin in 3 of 6391 domestic agricultural commodity
samples and 1 of 12044 imported samples, 1981-6, at concns ranging from 0.10
to 1.0 ppm and 1.0 ppm, respectively(2-3). For 1988, trifluralin was found in
4 of 13980 samples but it was not detected in 13085 samples from 1989(4).
Fish/Seafood Concentrations:
Trifluralin was qualitatively detected in dead carp taken from the Llobregat
River, Barcelona, Spain, 1984(1). Fish obtained from the Wabash River, IN, had
the following mean trifluralin levels: sauger, 10.2 ppm, shorthead redhorse,
5.38 ppm, and golden redhorse, 3.21 ppm(2).
Environmental Standards & Regulations:
FIFRA Requirements:
Tolerances are established for residues of the herbicide and plant growth
regulator trifluralin (alpha, alpha, alpha- trifluoro-2,6-dinitro-N,N-dipropyl-p-toludine)
in or on the following raw agricultural commodities: Alfalfa, hay; asparagus;
barley, hay; barley, straw; bean, mung, sprouts; carrot, roots; corn, field,
grain; corn, field, stover; corn, field, forage; cotton, undelinted seed; cress,
upland; flax, seed; fruit, citrus, group; fruit, stone group; grain, crops,
except corn, sweet and rice grain; grapes; hops; legumes, forage; nut, tree,
group; peanut; peppermint, tops; rapeseed; safflower seed; sorghum, fodder;
sorghum, forage; spearmint, tops; sugarcane, cane; sunflower seed; vegetable,
curcurbit, group; vegetable, fruiting, group; vegetables, leafy; vegetables,
root (exc. carrots); vegetables, seed and pod; wheat, grain; and wheat, straw.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive
review of older pesticides to consider their health and environmental effects
and make decisions about their future use. Under this pesticide reregistration
program, EPA examines health and safety data for pesticide active ingredients
initially registered before November 1, 1984, and determines whether they are
eligible for reregistration. In addition, all pesticides must meet the new safety
standard of the Food Quality Protection Act of 1996. Trifluralin is found on
List A, which contains most food use pesticides and consists of the 194 chemical
cases (or 350 individual active ingredients) for which EPA issued registration
standards prior to FIFRA, as amended in 1988. Case No: 0179; Pesticide type:
Herbicide (growth regulator); Registration Standard Date: 04/01/87; Case Status:
RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide
are eligible for reregistration, as reflected in a Reregistration Eligibility
Decision (RED) document.; Active ingredient (AI): Trifluralin; Data Call-in
(DCI) Date(s): 03/03/95, 04/30/96; AI Status: OPP has completed a Reregistration
Eligibility Decision (RED) document for the case/AI.
Acceptable Daily Intakes:
THE FAO/WHO HAS NOT ESTABLISHED ACCEPTABLE DAILY INTAKE OF TRIFLURALIN OR
ANY OTHER DINITROANILINE HERBICIDE.
CERCLA Reportable Quantities:
Persons in charge of vessels or facilities are required to notify the National
Response Center (NRC) immediately, when there is a release of this designated
hazardous substance, in an amount equal to or greater than its reportable quantity
of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In
the Washington D.C. metropolitan area (202) 426-2675. The rule for determining
when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Atmospheric Standards:
Listed as a hazardous air pollutant (HAP) generally known or suspected to
cause serious health problems. The Clean Air Act, as amended in 1990, directs
EPA to set standards requiring major sources to sharply reduce routine emissions
of toxic pollutants. EPA is required to establish and phase in specific performance
based standards for all air emission sources that emit one or more of the listed
pollutants. Trifluralin is included on this list.
Federal Drinking Water Guidelines:
EPA 5 ug/l
State Drinking Water Guidelines:
(AZ) ARIZONA 2 ug/l
(ME) MAINE 2 ug/l
(WI) WISCONSIN 7.5 ug/l
Allowable Tolerances:
Tolerances are established for residues of the herbicide and plant growth
regulator trifluralin (alpha, alpha, alpha- trifluoro-2,6-dinitro-N,N-dipropyl-p-toludine)
in or on the following raw agricultural commodities: Alfalfa, hay 0.2 ppm; asparagus
0.05 ppm; barley, hay 0.05 ppm; barley, straw 0.05 ppm; bean, mung, sprouts
2.0 ppm; carrot, roots 1.0 ppm; corn, field, grain 0.05 ppm; corn, field, stover
0.05 ppm; corn, field, forage 0.05 ppm; cotton, undelinted seed 0.05 ppm; cress,
upland 0.05 ppm; flax, seed 0.05 ppm; fruit, citrus, group 0.05 ppm; fruit,
stone group 0.05 ppm; grain, crops, except corn, sweet and rice grain 0.05 ppm;
grapes 0.05 ppm; hops 0.05 ppm; legumes, forage 0.05 ppm; nut, tree, group 0.05
ppm; peanut 0.05 ppm; peppermint, tops 0.05 ppm; rapeseed 0.05 ppm; safflower
seed 0.05 ppm; sorghum, fodder 0.05 ppm; sorghum, forage 0.05 ppm; spearmint,
tops 0.05 ppm; sugarcane, cane 0.05 ppm; sunflower seed 0.05 ppm; vegetable,
curcurbit, group 0.05 ppm; vegetable, fruiting, group 0.05 ppm; vegetables,
leafy 0.05 ppm; vegetables, root (exc. carrots) 0.05 ppm; vegetables, seed and
pod 0.05 ppm; wheat, grain 0.05 ppm; and wheat, straw 0.05 ppm.
Chemical/Physical Properties:
Molecular Formula:
C13-H16-F3-N3-O4
Molecular Weight:
335.28
Color/Form:
Yellow crystals
YELLOW-ORANGE PRISMS
Odor:
NO APPRECIABLE ODOR
Boiling Point:
139-140 deg C @ 4.2 mm Hg
Melting Point:
46-47 deg C
Corrosivity:
Technical not corrosive
Density/Specific Gravity:
1.36 @ 22 deg C
Octanol/Water Partition Coefficient:
log Kow= 5.34
Solubilities:
Solubility @ 25 deg C: > 100 g/100 ml acetone; 81 g/100 ml xylene
SOLUBILITY @ 25 DEG C: 7 G/100 ML ETHANOL
Sol at 25 deg C: > 100 g/100 ml acetonitrile; > 100 g/100 ml choloroform;
82 g/100 ml dimethylformamide; 83 g/100 ml dioxane; 5-6.7 g/100 ml hexane; 3-3.4
g/100 ml methanol; 44 g/100 ml methyl cellosolve; 88 g/100 ml methyl ethyl ketone
Slightly sol in water (0.0024 g/100 ml)
In water, 18.4 mg/l @ 25 deg C, pH= 5
Spectral Properties:
Intense mass spectral peaks: 306 m/z (100%), 264 m/z (97%), 43 m/z (95%),
41 m/z (35%)
Vapor Pressure:
4.58X10-5 mm Hg @ 25 deg C
Other Chemical/Physical Properties:
Henry's Law constant= 1.03X10-4 atm-cu m/mol @ 20 deg C
Chemical Safety & Handling:
Skin, Eye and Respiratory Irritations:
Cause eye irritation. May cause skin sensitization reactions in certain individuals.
Fire Potential:
TECHNICAL MATERIAL IS NOT FLAMMABLE. FOR FORMULATED CONCENTRATE USE ORDINARY
PRECAUTIONS FOR VOLATILE SOLVENTS.
Hazardous Decomposition:
When heated to decomposition it emits toxic fumes of /hydrogen fluoride
and nitrogen oxides/.
Susceptible to decomposition by ultraviolet radiation.
Preventive Measures:
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.
Stability/Shelf Life:
SHELF LIFE OF CONCENTRATE IS MORE THAN 2 YR
STABLE IN PURE STATE, IN LIQ OR IN GRANULAR FORMULATIONS
Stable though susceptible to decomposition by ultraviolet radiation.
Storage Conditions:
THIS PRODUCT IS STABLE UNDER NORMAL STORAGE CONDITIONS FOR A MINIMUM OF 3
YR WHEN STORED IN ADEQUATE PACKING IN METAL CONTAINERS WITH POLYETHYLENE LINING,
AT ROOM TEMP. THE BIOLOGICAL ACTIVITY OF DIGERMIN REMAINS PRACTICALLY UNVARIED
FOR 2 YR UNDER ENVIRONMENTAL CONDITIONS, PROVIDED THE PRODUCT IS STORED IN ITS
UNOPENED & UNDAMAGED ORIGINAL CONTAINERS, & IN SHADED & POSSIBLY
WELL-AIRED PLACES. AVOID FREEZING. STORE ABOVE 40 DEG F. DO NOT STORE NEAR HEAT
OR FLAME.
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.
Trifluralin is resistant to oxidation, and acid and alkaline hydrolysis. The
major environ effect of concern in the disposal of trifluralin is its toxicity
to fish. Trifluralin is known to be strongly adsorbed onto the soil and is resistant
to movement by water, and burial in specially designated landfills or isolated
areas away from water supplies is the procedure recommended for the disposal
of small quantities of trifluralin. For the decontamination of trifluralin containers,
the National Agricultural Chemical Association triple rinse and drain procedure
is recommended. Rinse soln from containers can be poured into the spray tank
for application. Trifluralin bags should be destroyed when empty and disposed
of through regular refuse collection system or buried in an isolated area away
from water supplies. Recommendable method: Landfill. Not recommendable methods:
Discharge to sewer, & thermal destruction.
Occupational Exposure Standards:
Manufacturing/Use Information:
Major Uses:
For Trifluralin (USEPA/OPP Pesticide Code: 036101) 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./
Herbicide
Manufacturers:
Dow AgroSciences LLC, 9330 Zionsville Rd., Indianapolis, IN 46268, (317) 337-3000;
Production site: not listed
Methods of Manufacturing:
REACTION OF 4-TRIFLUORO-2,6-DINITROCHLOROBENZENE AND DIPROPYLAMINE IN THE
PRESENCE OF SODIUM CARBONATE
General Manufacturing Information:
TRIFLURALIN IS TOLERATED AT 0.05 PPM BY MOST CROPS; EXCEPTIONS ARE ALFALFA
HAY (0.2 PPM), CARROTS (1 PPM), AND MUNG BEANS (2 PPM).
DETERMINATION OF GAS CHROMATOGRAPH AMENABLE NITROSAMINES IN HERBICIDE FORMULATIONS.
N-NITROSODIPROPYLAMINE WAS DETECTED IN TRIFLURALIN FORMULATIONS USING THERMAL
ENERGY ANALYZER AFTER SEPARATION BY GAS CHROMATOGRAPHY OR HPLC. IDENTITY OF
THE CMPD WAS CONFIRMED BY MASS SPECTROMETRY. RESULTS INDICATE THAT FORMULATIONS
OF AMINE SALTS CAN FORM NITROSAMINES ON STORAGE, AND NITROSAMINES CAN BE FORMED
IN PREPN OF NITROANILINE BASED HERBICIDES.
Formulations/Preparations:
USEPA/OPP Pesticide Code 036101; Trade Names: Treflan.
EMULSIFIABLE CONCENTRATE (4 LB TRIFLURALIN PER US GAL), GRANULAR 5%. PRODUCT
TO CONTAIN LESS THAN 1 PPM NITROSAMINE BY EPA ORDER.
Consumption Patterns:
SELECTIVE HERBICIDE FOR GRASSES & BROADLEAF WEEDS, OF WHICH 52% IS USED
ON SOYBEANS, 40% ON COTTON, 8% ON OTHER FIELD CROPS, VEGETABLES, FRUIT, NUTS,
NURSERY CROPS, ALFALFA, PASTURE LAND, & SUMMER FALLOW, & 2% AS SELECTIVE
HERBICIDE IN OTHER APPLICATIONS (1972)
(1975) 9.86X10+9 GRAMS (CONSUMPTION)
U. S. Production:
(1972) 9.53X10+9 GRAMS
U. S. Imports:
(1972) NEGLIGIBLE
U. S. Exports:
(1972) 1.82X10+9 GRAMS
Laboratory Methods:
Analytic Laboratory Methods:
Analytical method for residue determination requires extraction of crop tissue
or soil with a solvent ... removal of interfering substances on florisil column,
and determination by gas chromatography utilizing electron affinity detector.
AOAC Method 973.13. Benfluralin or trifluralin in pesticide formulations.
Ultraviolet spectroscopic method.
AOAC Method 973.4. Benfluralin or trifluralin in pesticide formulations. Gas
chromatographic method.
A QUANTITATIVE GAS LIQUID CHROMATOGRAPHY/MASS SPECTROMETRY PROCEDURE FOR DETERMINING
TRIFLURALIN RESIDUES IN SOIL IS DESCRIBED.
A SENSITIVE MULTIRESIDUE METHOD IS PRESENTED FOR DETECTION OF 7 NATURAL HERBICIDES
(INCL TRIFLURALIN) IN NATURAL WATERS WITH PRACTICAL DETECTION LIMITS BETWEEN
5 & 100 NG/L.
... TRIFLURALIN DETERMINATION IN FORMULATIONS BY GC, AFTER EXTRACTION WITH
WATER, WITH DIISOBUTYL PHTHALATE AS INTERNAL STD. SHOWS DATA FOR 3 TYPICAL FORMULATIONS.
A method was developed for the simultaneous extraction of trifluralin, methyl
paraoxon, methyl parathion, fenvalerate and 2,4-D dimethylamine salt in pond
water using a solid-phase C18 column. For trifluralin analysis, after elution
from the C18 column the eluate was cleaned up with activated alumina (less than
10 min contact time). A 1 ug spike of trifluralin dissolved in 5 ml solvent
and allowed to remain in contact with 2 g alumina for 30 min resulted in a 25%
loss of trifluralin. Analysis was then made on a capillary gas chromatograph
equipped with an electron-capture detector. Simultaneous extractions of trifluralin,
methyl paraoxon, methyl parathion, fenvalerate and 2,4-D dimethylamine salt
were obtained from 500 g fortified pond water (from wetlands in ND). At 1.0,
0.1, 0.01, and 0.001 ppm trifluralin, percent recoveries were 91 + or - 4.5,
90 + or - 5.3, 92 + or - 9.7 and 79 + or - 3.8%, respectively. Median recovery
for trifluralin was 91%.
Product analysis is by gas liquid chromatography with FID. Residues are determined
by gas liquid chromatography with electron capture detector.
Special References:
Special Reports:
NTP; Bioassay of Trifluralin for Possible Carcinogenicity CAS No. 1582-09-8
Report # 034 (1978). NIH Pub # 78-834.
USEPA; Health Advisories for 50 Psticides (Including Trifluralin) (1988) PB88-245931. Documents summarize health effects of 50 pesticides including trifluralin. Topics discussed include: General effects and properties; Pharmacokinetics; Health effects in humans and animals; Quantification of toxicological effects; Other criteria and standards, Analytical methods and treatment technologies.
Synonyms and Identifiers:
Synonyms:
L-36352
**PEER REVIEWED**
AGREFLAN
**PEER REVIEWED**
AGRIFLAN 24
**PEER REVIEWED**
BENZENAMINE, 2,6-DINITRO-N,N-DIPROPYL-4-(TRIFLUOROMETHYL)-
**PEER REVIEWED**
CRISALIN
**PEER REVIEWED**
DIGERMIN
**PEER REVIEWED**
2,6-DINITRO-N,N-DIPROPYL-4-(TRIFLUOROMETHYL)BENZENAMINE
**PEER REVIEWED**
2,6-DINITRO-N,N-DI-N-PROPYL-ALPHA,ALPHA,ALPHA-TRIFLUORO-P-TOLUIDINE
**PEER REVIEWED**
2,6-DINITRO-6-TRIFLUORMETHYL-N,N-DIPROPYLANILIN (GERMAN)
**PEER REVIEWED**
4-(DI-N-PROPYLAMINO)-3,5-DINITRO-1-TRIFLUOROMETHYLBENZENE
**PEER REVIEWED**
N,N-DI-N-PROPYL-2,6-DINITRO-4-TRIFLUOROMETHYLANILINE
**PEER REVIEWED**
N,N-DIPROPYL-4-TRIFLUOROMETHYL-2,6-DINITROANILINE
**PEER REVIEWED**
ELANCOLAN
**PEER REVIEWED**
LILLY 36,352
**PEER REVIEWED**
NCI-C00442
**PEER REVIEWED**
NITRAN
**PEER REVIEWED**
OLITREF
**PEER REVIEWED**
SU SEGURO CARPIDOR
**PEER REVIEWED**
P-TOLUIDINE, ALPHA,ALPHA,ALPHA-TRIFLUORO-2,6-DINITRO-N,N-DIPROPYL-
**PEER REVIEWED**
TREFICON
**PEER REVIEWED**
TREFLAM
**PEER REVIEWED**
TREFLAN
**PEER REVIEWED**
Treflan EC
**PEER REVIEWED**
TREFLANOCIDE ELANCOLAN
**PEER REVIEWED**
TRIFLUORALIN
**PEER REVIEWED**
ALPHA,ALPHA,ALPHA-TRIFLUORO-2,6-DINITRO-N,N-DIPROPYL-P-TOLUIDINE
**PEER REVIEWED**
TRIFLURALINE
**PEER REVIEWED**
TRIFUREX
**PEER REVIEWED**
TRIKEPIN
**PEER REVIEWED**
TRIM
**PEER REVIEWED**
Formulations/Preparations:
USEPA/OPP Pesticide Code 036101; Trade Names: Treflan.
EMULSIFIABLE CONCENTRATE (4 LB TRIFLURALIN PER US GAL), GRANULAR 5%. PRODUCT
TO CONTAIN LESS THAN 1 PPM NITROSAMINE BY EPA ORDER.
RTECS Number:
NIOSH/XU9275000
Administrative Information:
Hazardous Substances Databank Number: 1003
Last Revision Date: 20010809
Last Review Date: Reviewed by SRP on 1/20/2001
Update History:
Complete Update on 08/09/2001, 1 field added/edited/deleted.
Complete Update on 04/26/2001, 42 fields added/edited/deleted.
Complete Update on 03/22/2000, 1 field added/edited/deleted.
Complete Update on 03/09/2000, 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 08/26/1999, 1 field added/edited/deleted.
Complete Update on 03/29/1999, 1 field added/edited/deleted.
Complete Update on 03/01/1999, 1 field added/edited/deleted.
Complete Update on 06/02/1998, 1 field added/edited/deleted.
Complete Update on 10/20/1997, 1 field added/edited/deleted.
Complete Update on 08/11/1997, 1 field added/edited/deleted.
Complete Update on 04/07/1997, 2 fields added/edited/deleted.
Complete Update on 02/28/1997, 1 field added/edited/deleted.
Complete Update on 09/17/1996, 1 field added/edited/deleted.
Complete Update on 01/21/1996, 1 field added/edited/deleted.
Complete Update on 12/22/1994, 1 field added/edited/deleted.
Complete Update on 11/15/1994, 1 field added/edited/deleted.
Complete Update on 09/08/1994, 2 fields added/edited/deleted.
Complete Update on 09/01/1994, 4 fields added/edited/deleted.
Field Update on 03/21/1994, 1 field added/edited/deleted.
Field Update on 09/15/1993, 1 field added/edited/deleted.
Field update on 12/17/1992, 1 field added/edited/deleted.
Complete Update on 08/17/1992, 3 fields added/edited/deleted.
Complete Update on 07/02/1992, 55 fields added/edited/deleted.
Field Update on 09/12/1991, 1 field added/edited/deleted.
Field Update on 09/10/1991, 1 field added/edited/deleted.
Complete Update on 10/10/1990, 2 fields added/edited/deleted.
Complete Update on 06/04/1990, 7 fields added/edited/deleted.
Field Update on 05/14/1990, 1 field added/edited/deleted.
Field Update on 03/06/1990, 1 field added/edited/deleted.
Complete Update on 10/03/1989, 1 field added/edited/deleted.
Complete Update on 06/19/1989, 2 fields added/edited/deleted.
Complete Update on 03/01/1985