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Fluometuron. TOXNET profile from Hazardous Substances Data Base.
from: http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB
FLUOMETURON
CASRN: 2164-17-2Human Health Effects
Evidence for Carcinogenicity:
No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
Human Toxicity Excerpts:
... Mild cholinesterase inhibitor & /causes/ ... an increased leukocyte count in circulating blood in exposed agricultural workers.
No data on humans was available. No evaluation of the carcinogenicity of fluormeturon in humans can be made. ... No data on humans was available.
A frequency of 5.8% of aberrant metaphases was observed in peripheral leukocytes from sowers exposed to an air concn of 4.28-10.90 mg/cu m of a commercial fluometron; a frequency of 4.3% was seen in leukocytes of tractor drivers exposed to concn or 0.64-7.4 mg/cu m, compared with 2.5 % prior to exposure.
DUST MAY BE IRRITATING TO THE EYE ... .
Skin, Eye and Respiratory Irritations:
DUST MAY BE IRRITATING TO THE EYE ... .
Medical Surveillance:
Medical Testing: If symptoms develop or overexposure is suspected, the following may be useful: Liver function tests. Complete blood count. Evaluation by a qualified allergist, including careful exposure history and special testing, may help diagnose skin allergy. Any evaluation should include a careful history of past and present symptoms with an exam. Medical tests that look for damage already done are not a substitute for controlling exposure.
Probable Routes of Human Exposure:
NIOSH (NOES Survey 1983) has statistically estimated that 645 workers are potentially exposed to fluometuron in the USA(1). The NOES Survey does not include farm workers. Occupational exposure to fluometuron may occur through inhalation of dust particles and dermal contact with this compound at workplaces where fluometuron is produced or used(SRC). Field air samples taken from a farm in Tashkent, Uzbekistan in the 1970's indicated that tractor operators were exposed to 0.64-7.4 mg/cu m and seeders to 4.28-10.98 mg/cu m of fluometuron(2).
Emergency Medical Treatment:
Emergency Medical Treatment:
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The following Overview, *** HERBICIDES: UREA-SUBSTITUTED ***, 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 On the basis of animal feeding studies these agents
appear to have low systemic toxicity. Severity of
intoxication should be based on clinical findings.
Methemoglobinemia may be noted in large ingestions.
o If severe symptoms or signs of poisoning are evident,
other than methemoglobinemia, the operation of an
alternative or additional toxicant should be suspected.
HEENT
0.2.4.1 ACUTE EXPOSURE
o Eye exposure may result in ocular irritation.
Irritation of the respiratory mucous membranes may be
noted following prolonged heavy contact.
CARDIOVASCULAR
0.2.5.1 ACUTE EXPOSURE
o CNS depression and hypoxemia may be noted if
methemoglobinemia is present.
GASTROINTESTINAL
0.2.8.1 ACUTE EXPOSURE
o Nausea, vomiting, and diarrhea may be noted following
ingestion.
GENITOURINARY
0.2.10.1 ACUTE EXPOSURE
o Some metabolites may cause irritation of the urinary
tract.
HEMATOLOGIC
0.2.13.1 ACUTE EXPOSURE
o Sulfhemoglobin has been observed in the blood of rats
and dogs given repeated large doses of diuron, and in
one human overdose of monolinuron. Methemoglobinemia
may result from effects of metabolites of some
urea-based herbicides.
DERMATOLOGIC
0.2.14.1 ACUTE EXPOSURE
o Cyanosis unresponsive to oxygen therapy may be noted in
patients with methemoglobinemia due to absorption of
excessive amounts of these agents.
|
| Laboratory: |
o Plasma levels are not clinically useful.
o Obtain methemoglobin concentrations in all cyanotic
patients and patients demonstrating dyspnea or other signs
of respiratory difficulty.
|
| Treatment Overview: |
ORAL EXPOSURE
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 DECONTAMINATION - Remove contaminated clothing and wash
affected areas including the hair thoroughly with soap
and water.
o NATIONAL PESTICIDE TELECOMMUNICATIONS NETWORK -
1. Provides consultation to poison centers and other
health professionals for the management of pesticide
poisoning. Calls regarding emergency cases requiring
immediate medical response will be transferred to the
Oregon Poison Center. The National Pesticide
Telecommunications Network has a toll-free number,
1-800-858-7378, or if outside the U.S., the
non-toll-free number is 541-737-6094. Hours are 6:30
AM to 4:30 PM Pacific time 7 days/week excluding
holidays. FAX: 1-541-737-0761. email:
nptn@ace.orst.edu
o TREATMENT IS PRIMARILY symptomatic and supportive.
o METHEMOGLOBINEMIA: Administer 1 to 2 mg/kg of 1%
methylene blue slowly IV in symptomatic patients.
Additional doses may be required.
INHALATION EXPOSURE
o 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.
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 Insufficient data in the literature to accurately assess
the minimal toxic or lethal dose. Severity of
intoxication should be based on clinical findings.
o On the basis of animal studies these agents appear to have
a low order of systemic toxicity.
|
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:
No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
Non-Human Toxicity Excerpts:
DERMAL APPLICATIONS TO RABBITS AT 400 MG/KG (10 DAY EXPOSURE) HAD NO EFFECT; RATS FED 12 MO @ 10 MG/KG/DAY ... & DOGS @ 15 MG/KG/DAY LEVEL WERE UNAFFECTED.
IT HAS LOW TOXICITY TO BIRDS; THERE WAS NO MORTALITY OF RAINBOW TROUT, GAMMARUS AND TUBIFEX SPECIES, EXPOSED TO CONCN OF 60 PPM.
SKIN SENSITIZATION (GUINEA PIG): NOT A SENSITIZER. SYMPTOMS OF POISONING: DEPRESSION, HYPERPNEA, EMESIS, COMA, DEATH.
FLUOMETURON IS CONSIDERED TO BE RELATIVELY NONTOXIC TO ... WILDLIFE, & BEES. ... IN 90 DAY FEEDING STUDIES, A DIETARY LEVEL OF 1000 PPM (75 MG/KG/DAY) FLUOMETURON TECHNICAL WAS DETERMINED TO BE WITHOUT EFFECT IN RATS ... .
/ACUTE SYMPTOMS IN MALLARDS AFTER ORAL ADMIN ARE/ ATAXIA, WING DROP OR WINGS CROSSED HIGH OVER BACK, TAIL POINTED UPWARD, FLUFFED FEATHERS, HYPEREXCITABILITY, PHONATION, FALLING. SIGNS APPEARED 15 MIN AFTER-TREATMENT & PERSISTED FOR UP TO ONE WK.
Groups of 50 male and 50 female B6C3F1 hybrid mice, seven wk old, were fed diets containing 500 or 1000 mg/kg fluometuron (99% pure; impurities not specified) mixed with corn oil for 103 wk; 25 female and 25 male matched controls received a diet containing 2% corn oil. The mice were observed for another wk before they were killed. Survival to the end of the study among male mice was 14/25 (56%) of the controls, 33/50 (66%) of the low dose and 32/50 (64)% of the high dose group; among females, 16/25 (64%) of the controls, 38/50 (76%) of the low dose and 33/50 (66%) of the high dose group were still alive at that time. Mean body weights of dosed and control mice were comparable throughout the study. Neoplastic and non-neoplastic lesions occurred in similar incidences among control and dosed mice, with the exception of tumors of the liver & of the hematopoietic system in male mice: there were 3/21 (14%) hepatocellular carcinomas in controls, 8/47 (17%) in the low-dose group, and 15/49 (31%) in the high dose group.
Groups of 50 male and 50 female Fischer 344 rats, seven wk old, were fed diets containing 0, 125 or 250 mg/kg fluometuron (99% pure; impurities not specified) with corn oil for 103 wk. Corn oil was also added to control diet at a concn of 2%. Animals were observed for an additional wk. Mean body weights of dosed and control rats were comparable throughout the study. Of the male rats, 38/50 (76%) of the controls, 37/50 (74%) fed 125 mg/kg and 44/50 (88%) fed 250 mg/kg were still alive at 90 wk; at that time, of the females, 44/50 (88%) of controls, 47/50 (94%) fed 125 mg/kg and 48/50 (96%) fed 250 mg/kg were still alive. Although a number of tumors were noted in controls as well as dosed rats, no statistically significant difference was observed between exposed and control animals.
In 90 day feeding studies with Fischer 344 rats, a two fold increase in the weight of the spleen was seen in males fed 4000 mg/kg of diet and in females fed 2000 or 4000 mg/kg of diet. A dose related increase in the incidence of red blood cells with polychromasia & anisocytosis was also observed. Mean body weight gain of females was depressed more than 10% by doses of 4000 mg/kg in the diet.
Treatment of Vicia faba root tips with up to 90 mg/l of a commercial formulation for 24 & 72 hr induced low levels of mitotic aberration. ... Treatment of cotton seeds with 0.01-1% of a commercial formulation resulted in dose and time dependent increases in chromosomal aberrations ... .
Differential metabolism is one of the major factors responsible for the selectivity of phenylurea herbicides. In particular, cotton exhibited a remarkable ability to degrade ... fluometron. /Phenylurea herbicides/
Fluometuron tested negatively for mutagenicity in Salmonella assays.
The available data are inadequate to evaluate the carcinogenicity of fluometuron in experimental animals.
Slightly irritating to skin and mildly irritating to eye of rabbit. May be a skin sensitizer.
In 90 day feeding trials, no effect level for rats was 100 mg/kg diet, and for dogs 400 mg/kg diet.
When diuron and fluometuron were added to a nutrient solution in a concn of 2X10-5 M, they severely inhibited carbon dioxide uptake in carrot plants.
A commercial formulation of fluometron was ineffective in inducing mitotic gene conversion in Saccharomyces cerevisiae strain D4 without exogenous metabolic activation.
National Toxicology Program Studies:
Groups of 50 /B6C3F1/ mice of each sex were fed diets containing 500 or 1,000 ppm of fluometuron for 103 weeks. Matched controls consisted of groups of 25 untreated mice of each sex. All surviving animals were killed at 103 to 105 weeks. Mean body weights of the dosed groups of male and female mice were essentially the same as those of the corresponding control groups. Survival of dosed groups of mice were similar to that of the corresponding control groups. Similarities between mean body weights and survival between dosed and control animals in the chronic study suggest that these animals could have tolerated higher doses. ... The only possible carcinogenic effects from compound administration were in male mice. Incidences of hepatocellular carcinomas or adenomas in male mice were dose related, and the incidence in the high-dose group was marginally higher than that in the corresponding matched controls or pooled controls from concurrent studies. ... Under the conditions of this bioassay, fluometuron was not carcinogenic for female B6C3F1 mice. Equivocal results were obtained for male B6C3F1 mice which may have had an increased incidence of hepatocellular tumors.
Groups of 50 /F344/ rats of each sex were fed diets containing 125 or 250 ppm of fluometuron for 103 weeks ... Matched controls consisted of groups of 50 untreated rats of each sex. All surviving animals were killed at 103 to 105 weeks. Splenomegaly observed in rats in the subchronic studies influenced selection of doses for the chronic study; however, no splenic effects were observed in the chronic study. Mean body weights of the dosed groups of male and female rats ... were essentially the same as those of the corresponding control groups. Survival of dosed groups of rats ... was similar to that of the corresponding control groups. Similarities between mean body weights and survival between dosed and control animals in the chronic study suggest that these animals could have tolerated doses. Under the conditions of this bioassay, fluometuron was not carcinogenic for F344 rats.
Non-Human Toxicity Values:
LD50 Rat oral 6416-8900 mg/kg
LD50 Rat percutaneous >2000 mg/kg
LD50 Rabbit percutaneous >10,000 mg/kg
LD50 Rat oral 6416 mg/kg
LD50 Rat ip 685 mg/kg
LD50 Mouse oral 900 mg/kg
LD50 Mouse ip 522 mg/kg
LD50 Rabbit oral 2500 mg/kg
LD50 Guinea pig oral 810 mg/kg
Ecotoxicity Values:
LC50 Salmo gairdneri (Rainbow trout) 3.0 mg/l/96 hr @ 12 deg C (95% confidence interval 2.0- 4.5 mg/l), wt 0.7 g. 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 Ictalurus punctatus (Channel catfish) 0.6 mg/l/96 hr @ 18 deg C (95% confidence interval 0.3-1.3 mg/l), wt 0.8 g. 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.
LD50 Anas platyrhynchos (Mallard) oral >2000 mg/kg
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
... FLUOMETURON WAS METABOLIZED IN VIVO, PRIMARILY BY LIVER, TO N-DESMETHYL & N-DEMETHYLATED ANALOGS ... A SMALL AMT WAS EXCRETED AS ANILINE ANALOG. NO LABELED CO2 WAS DETECTED DURING FIRST 48 HR. AFTER TREATMENT OF CUCUMBERS & COTTON WITH FLUOMETURON, (14)C-METABOLITES WERE DETERMINED BY AUTORADIOGRAPHY. MONOMETHYLATED, DEMETHYLATED, & ANILINE DERIVATIVES WERE IDENTIFIED FROM COTTON. ONLY MONO- & DE-METHYLATED DERIVATIVES WERE IDENTIFIED FROM CUCUMBER.
FLUOMETURON HAS BEEN SHOWN TO UNDERGO A 3 STEP DEGRADATION PROCESS IN PLANTS. THE FIRST TWO STEPS ARE DEMETHYLATION TO A MONOMETHYL THEN TO A DEMETHYLATED INTERMEDIATE. THE THIRD STEP IS DEAMINATION-DECARBOXYLATION STEP THAT PRODUCES AN ANILINE MOLECULE.
Ring hydroxylation of phenylureas in animal tissues ... has been observed with fluometuron.
Cmpd that are rapidly translocated to aerial parts, such as ... fluometuron ... would be expected to be metabolized in the leaves.
Human embryonic lung cell homogenate metabolized small amounts of fluometuron through oxidative pathways to N-(3-trifluoromethylphenyl)-N'-formyl-N'-methylurea, N-(3-trifluoromethylphenyl)-N'-methylurea, and N-(3-trifluoromethylphenyl)urea.
The metabolism of fluometuron in corn (Zea mays variety Dixie 18) and wheat (Triticum aestivum variety Wakeland) was studied. In both species, metabolism involved two step demetted. Further metabolism of the aniline derivative into numerous metabolites occurred with an indication of formation of the hydroxyaniline derivative.
Sour orange (Citrus auranthium Leguminatae) or sweet lime (Citrus limetioides Tanaka) were exposed to (14)C fluometuron. After 4 days, analyses showed the presence of desmethylfluometuon, 3-trifluoromethylphenyl urea, and 3-trifluoromethylaniline.
After incubation of fluometuron with Rhizopus japonicus, desmethylfluometuron was observed.
When (14)C fluometuron was incubated with human embryonic lung (HEL) cells, more than 95% was recovered unchanged. Three metabolites were identified: 1-formyl-1-methyl-3-(3-trifluoromethylphenyl)urea; 1-methyl-3- (3-trifluoromethylphenyl)urea; and 3-trifluoromethylphenylurea.
Absorption, Distribution & Excretion:
... UPTAKE BY ROOTS & TRANSLOCATION TO AERIAL PARTS OF (14)C-LABELED ... FLUOMETURON IN FRENCH DWARF BEAN SEEDLINGS, CULTURED IN NUTRIENT SOLN SUPPLIED WITH 2.5 PPM (AND EQUAL CONCN OF RADIOACTIVITY) OF ... HERBICIDE /WAS STUDIED/. ... FLUOMETURON ... /WAS/ RAPIDLY TRANSLOCATED INTO LEAVES. IN CONTRAST /TO BEING/ ... CONFINED TO TRACHEAL VEINS, FLUOMETURON HAD ALMOST COMPLETELY MOVED OUT INTO THE MESOPHYLL TISSUES.
FLUOMETURON IS MORE READILY ABSORBED BY ROOTS FROM SOIL APPLICATION THAN FROM FOLIAR APPLICATION. FOLIAR ABSORPTION IS AIDED BY ADDING SURFACTANT OR NONPHYTOTOXIC OIL TO SPRAY SOLN. ... TRANSLOCATION OF ROOT ABSORBED. ... IS VIA APOPLAST TO UPPER PLANT PARTS. FOLIAR APPLICATIONS ARE ALSO TRANSLOCATED IN APOPLAST ... .
Mechanism of Action:
THE PRIMARY SITE OF FLUOMETURON ACTION IS INHIBITION OF THE HILL REACTION. THIS INVOLVES THE OXYGEN EVOLUTION SITE IN THE PHYTOSYSTEM II. THE INHIBITION PREVENTS THE FORMATION OF ATP & NADPH WHICH ARE NECESSARY FOR CARBON DIOXIDE FIXATION.
Pharmacology:
Environmental Fate & Exposure
Environmental Fate/Exposure Summary:
Fluometuron's use as an herbicide for the control of broadleaf weeds and grass is expected to result in its direct release to the environment. If released to air, a vapor pressure of 9.38X10-7 mm Hg at 25 deg C indicates fluometuron will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluometuron will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2.1 days. Particulate-phase fluometuron will be removed from the atmosphere by wet and dry deposition. Fluometuron may photodegrade in the atmosphere based upon its photolysis in water. The photolysis half-life of 10 mg/l aqueous solution of fluometuron with natural sunlight was 1.2 days. If released to soil, fluometuron is expected to have high mobility based upon its Koc ranging from 29 to 173. Volatilization from moist soil surfaces is not expected to be an important fate process based upon its Henry's Law constant of 2.6X10-9 atm-cu m/mole. In soil, fluometuron is transformed primarily through biodegradation. Depending on the nature of soil and climatic conditions, the field half-lives of fluometuron in soil ranged from 10-171 days with an average half-life of 85 days. The major degradation product under aerobic and anaerobic conditions was mono-N-demethylated fluometuron. Fluometuron residues often dissipate to nondetectable levels by four months after application of labeled rates. Half-lives in dissipation studies conducted in cotton fields and sampling at 0 to 15 cm were: 103 days for a loamy sand with 0.9% organic matter and pH 6.4 in Georgia; and 171 days for a sandy loam with 1.3% organic matter and pH 7.3 in California. If released into water, fluometuron is not expected to adsorb to suspended solids and sediment based upon its Koc values. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's Henry's Law constant. An estimated BCF of 15 suggests the potential for bioconcentration of fluometuron in aquatic organisms is low. Hydrolysis is not expected to be an important fate process based upon its hydrolysis half-lives in water of 2.4 yrs (pH 5) and 2.8 yrs (pH 9). Occupational exposure to fluometuron may occur through inhalation of dust particles and dermal contact with this compound at workplaces where fluometuron is produced or used. (SRC)
Probable Routes of Human Exposure:
NIOSH (NOES Survey 1983) has statistically estimated that 645 workers are potentially exposed to fluometuron in the USA(1). The NOES Survey does not include farm workers. Occupational exposure to fluometuron may occur through inhalation of dust particles and dermal contact with this compound at workplaces where fluometuron is produced or used(SRC). Field air samples taken from a farm in Tashkent, Uzbekistan in the 1970's indicated that tractor operators were exposed to 0.64-7.4 mg/cu m and seeders to 4.28-10.98 mg/cu m of fluometuron(2).
Natural Pollution Sources:
Fluometuron is not known to occur naturally(1).
Artificial Pollution Sources:
Fluometuron's use as an herbicide(1) is expected to result in its direct release to the environment(SRC).
Environmental Fate:
TERRESTRIAL FATE: IT IS OF INTERMEDIATE PERSISTENCE WITH A HALF-LIFE OF 60-75 DAYS ACCORDING TO SOIL CONDITIONS.
Terrestrial Fate: Fluometuron decreased from 6 ppm to < 0.5 ppm in approximately 165 days in the 0 to 5 cm layer of a plant-free Swiss clay loam under field conditions. Soil compostion: 18% clay, 12% silt, 67% sand, < 1% humus; pH 5.7. Herbicide applied at the rate of 4 kg active ingredient/ha. /From figure/
TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values ranging from 29 to 173(2-7), indicates that fluometuron is expected to have very high to moderate mobility in soil(SRC). Volatilization of fluometuron from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.6X10-9 atm-cu m/mole(8). Fluometuron is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.38X10-7 mm Hg(9). Biodegradation will be the major process by which fluometuron will be lost from most soils(5). Depending on the nature of soil and climatic conditions, the field half-lives of fluometuron in soil ranged from 10-171 days(5,10-12) with an average half-life of 85 days(7). Some loss of fluometuron from soil surface may occur as a result of photolysis by sunlight(13). The photolysis half-life was 9.7 days on a sandy loam soil at 10 to 36 deg C under natural light; the major photolysis product was the mono-N-demthylated metabolite [N-methyl-N'-[3-(trifluoromethyl)phenyl]urea](13). Based on its slow rate of hydrolysis in water (half-lives ranging from 2.4 to 2.8 years)(10), hydrolysis of fluometuron in moist soil is not expected to be important(SRC).
TERRESTRIAL FATE: Fluometuron residues often dissipate to nondetectable levels by four months after application of labeled rates. Half-lives in dissipation studies conducted in cotton fields and sampling at 0 to 15 cm were: 103 days for a loamy sand with 0.9% organic matter and pH 6.4 in Georgia; and 171 days for a sandy loam with 1.3% organic matter and pH 7.3 in California(1). Application rate and weather conditions can significantly impact half-life. In field experiments conducted in cotton grown in Georgia and California, no quantifiable fluometuron residues (limit of detection = 10 ppb) were found below 30 cm (12 inches)(1). Volatilization of fluometuron is negligible(1).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 29-173(2-7), indicate that fluometuron is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(8) based upon a Henry's Law constant of 2.6X10-9 atm-cu m/mole(9). According to a classification scheme(10), an estimated BCF of 15(SRC), from its log Kow of 2.42(11) and a regression-derived equation(12), suggests the potential for bioconcentration in aquatic organisms is low. Based on its observed biodegradation rate in soil (half-lives ranging from 10-171 days)(13-15), biodegradation of fluometuron in water is expected to be an important fate process(SRC). Photolysis in water is expected to occur based upon an experiment in which 10 mg/l of fluometuron had a half-life of 1.2 days with exposure to natural sunlight(16). Based on its slow rate of hydrolysis in water (half-life ranging from 2.4 to 2.8 years)(15), hydrolysis of fluometuron in water is not expected to be important(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluometuron, which has a vapor pressure of 9.38X10-7 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fluometuron 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 2.1 days(SRC), calculated from its rate constant of 7.6X10-12 cu cm/molecule-sec at 25 deg C(SRC) determined using a structure estimation method(3). Particulate-phase fluometuron may be removed from the air by wet and dry deposition(SRC). Fluometuron may photolyze in the atmosphere based upon its photolysis in water. At a concentration of 10 mg/l in water, fluometuron had a half-life of 1.2 days with exposure to natural sunlight(4).
Environmental Biodegradation:
The 3-trifluoromethyl moiety of fluometuron seems to be accessible to some extent to biochemical transformation reactions. A slight but measurable amount of radioactivity (< 5% of the dose applied) evolved as carbon dioxide during the 52 day observation period on incubation of the (14)C trifluoromethyl-labeled herbicide in soils. Oxidation of the trifluoromethyl carbon represents a minor pathway of degradation for fluometuron in the soil.
THE PATHWAY OF DEGRADATION OF FLUOMETURON IN A SANDY LOAM SOIL INVOLVED 2 STEP DEALKYLATION ... FOLLOWED BY HYDROLYSIS TO FORM ANILINE DERIVATIVE ... SOME ... (14)CO2 WAS OBSERVED. MONO- AND DI-DEMETHYL COMPD ... /AND/ ANILINE PRODUCT WERE OBSERVED.
After 35 days incubation, Rhizoctonia solani degraded 88% of (14)C- fluometuron to polar and water-soluble metabolites. No (14)CO2 was observed. Two major metabolites were identified by TLC and UV as 1-methyl-3-(3-trifluoromethylphenyl)urea and 3-trifluoromethylphenylurea. Five other metabolites were not identified.
AEROBIC: Several pure cultures of microorganisms degrade fluometuron(1-2). The biodegradation proceeds by two successive dealkylation to the corresponding 3-(trifluoromethylphenyl) urea which then hydrolyze to the corresponding aniline(1,3). Mixed populations of microorganisms from two soils also metabolized fluometuron in a similar way and the 3-(trifluoromethyl) aniline formed was immediately acetylated to the corresponding acetanilide(4). The release of carbon dioxide observed during the biodegradation of fluometuron(5) may at least be partly the result of the hydrolysis of phenylurea to the aromatic amine and not from ring cleavage(4). The half-life of fluometuron in unsterilized surface soil in the dark was 18 days compared to 315 days in sterilized soil(6). Biodegradation has also been observed in cover crop residues on the soil surface(7). In annual ryegrass, fluometuron was demethylated, at rates similar to those in soils, when the crop had high (78%) moisture conditions(7). The half-life of fluometuron was 189 days for aerobic microbial metabolism in a sandy loam soil at 25 deg C(8). The major degradation product under aerobic and anaerobic conditions was mono-N-demethylated fluometuron. Microbial metabolism is the most important contributor to field dissipation, but rates are moderate(8). In soil, microbial degradation is significant and rapid, with continual liberation of carbon dioxide(9).
ANAEROBIC: The half-life of fluometuron was 378 days in a sandy loam soil at 25 deg C under anaerobic conditions(1).
Environmental Abiotic Degradation:
The rate constant for the vapor-phase reaction of fluometuron with photochemically-produced hydroxyl radicals has been estimated as 7.6X10-12 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The hydrolysis half-life of fluometuron in water is 2.4 yrs at pH 5 and 2.8 yrs at pH 9(2,3). Therefore, hydrolysis of fluometuron in water is not expected to be important degradation pathway. When irradiated by a Rayonet photoreactor fitted with sunlamps, the photolysis half-life of a 90 mg/l aqueous solution of fluometuron at 50 deg C was 4.2 hr(4).The photolysis is also sensitized by methylene blue, particularly at basic pH(5). The photolysis half-life of 10 mg/l aqueous solution of fluometuron with natural sunlight was 1.2 days(6). The photolysis half-life was 9.7 days on a sandy loam soil at 10 to 36 deg C under natural light; the major photolysis product was the mono-N-demethylated metabolite [N-methyl-N'-[3-(trifluoromethyl)phenyl]urea](6). Photodegradation losses are substantial when little or no rainfall is received soon after application, but are moderate to slow with adequate rainfall(6).
Environmental Bioconcentration:
An estimated BCF of 15 was calculated for fluometuron(SRC), using a log Kow of 2.42 (1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. However, in a study of unicellular green algae (Chlorella fusca), a log BCF of 1.96(4) was determined for fluometuron, corresponding to a BCF of 91.2 and indicating a moderate potential for bioconcentration in algae.
Soil Adsorption/Mobility:
Experimental Koc values for fluometuron in soil range from 29 to 173(1-6). This range of the Koc values indicate that fluometuron would have very high to moderate mobility in soil(7). Soil thin layer chromatography studies confirm that fluormeturon adsorbs weakly to moderately to soil based on experimental Rf values determined in 13 soils (organic matter 0.36-10.26%) ranging from 0.17 to 0.89(8-10). The Koc for fluometuron ranges from 29 to 200 for various soil types (including sandy and loam soils)(11). It is moderately leachable in all but very sandy soils; the Koc value range from 31 to 117 (8 soil types); Kd = 0.15 to 1.13(12). The adsorption of fluometuron increases with increases in organic content(13,14) and clay content of soil(14).
Volatilization from Water/Soil:
The Henry's Law constant for fluometuron is 2.6X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that fluometuron is expected to be essentially nonvolatile from water and moist soil surfaces(2). Fluometuron is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.38X10-7 mm Hg(3).
Environmental Water Concentrations:
GROUNDWATER: Based on the records maintained in the STORET database of EPA, fluometuron was not detected in any of the 156 groundwater samples analyzed from 125 locations in the U.S.(1). Fluometuron was not detected (detection limit 0.5 ug/l) in water from 119 wells, springs and municipal drinking water supplies sampled throughout Arkansas, during 1985-1987(2). In a study of groundwater sampled in 1992-1998 from 231 wells in 14 counties in the Arkansas Delta, fluometuron was detected at high and persistent concentrations in two of the wells, at 0.4-0.9 ug/l in a well used for a machine shop and at 19-24 ug/l in a well designated for domestic use(3).
SURFACE WATER: Based on the records maintained in the STORET database of EPA, fluometuron was not detected in 14 surface water samples from 14 locations in the US(1). In a study of the Mississippi River and its tributaries in July/Aug 1991, fluometuron was detected in three tributaries and at three Mississippi River sites at concns of 9-411 ng/l(2).
Environmental Standards & Regulations:
FIFRA Requirements:
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. Fluometuron 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: 0049; Pesticide type: herbicide; Registration Standard Date: 12/17/85; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Fluometuron; Data Call-in (DCI) Date(s): 09/11/91, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
A tolerance is established for negligible residues of the herbicide fluometuron (1,1-dimethyl-3-(alpha, alpha, alpha-trifluoro-m-toly)urea) in or on the following raw agricultural commodity: cotton, undelinted seed.
Federal Drinking Water Guidelines:
EPA 90 ug/l
State Drinking Water Guidelines:
(FL) FLORIDA 91 ug/l
(ME) MAINE 90 ug/l
Allowable Tolerances:
A tolerance is established for negligible residues of the herbicide fluometuron (1,1-dimethyl-3-(alpha, alpha, alpha-trifluoro-m-toly)urea) in or on the following raw agricultural commodity: cotton, undelinted seed, 0.1 ppm.
Chemical/Physical Properties:
Molecular Formula:
C10-H11-F3-N2-O
Molecular Weight:
232.21
Color/Form:
White crystals
Colorless crystals
Odor:
Odorless
Boiling Point:
approx. 280 deg C @ 760 mm Hg
Melting Point:
163-164.5 deg C
Density/Specific Gravity:
1.39 g/cu cm (20 deg C)
Octanol/Water Partition Coefficient:
log Kow= 2.42
Solubilities:
Sol in N,N-dimethylformamide, acetone, ethanol, isopropanol, and other org solvents
Sol (20 deg C): 23 g/l dichloromethane; 170 mg/l hexane; 110 g/l methanol; 22 g/l octan-1-ol.
Solubility in acetone: 3 ppm
110 mg/l @ 22 deg C
Spectral Properties:
Intense mass spectral peaks: 72 m/z (100%), 232 m/z (25%), 44 m/z (22%), 42 m/z (11%)
Vapor Pressure:
9.38X10-7 mm Hg @ 25 deg C
Other Chemical/Physical Properties:
MP: ABOUT 155 DEG C; NONCORROSIVE /TECHNICAL PRODUCT/
On hydrolysis at 20 deg C, 50% loss (calc) occurs in 1.6 yr at pH 1, 2.4 yr at pH 5, 2.8 yr at pH 9.
Henry's Law constant= 2.60X10-9 atm-cu m/mole @ 25 deg C
Chemical Safety & Handling:
Skin, Eye and Respiratory Irritations:
DUST MAY BE IRRITATING TO THE EYE ... .
Hazardous Decomposition:
When heated to decomposition it emits very toxic fumes of /hydrogen fluoride and nitrogen oxides/.
Preventive Measures:
SAFETY PRECAUTIONS FOR HANDLING & APPLICATION: (A) KEEP OUT OF REACH OF CHILDREN & DOMESTIC ANIMALS, (B) MAY BE HARMFUL IF SWALLOWED, (C) AVOID INHALING DUST; DUST MAY BE IRRITATING TO THE EYE, & (D) WASH HANDS WITH SOAP & WATER BEFORE EATING, DRINKING OR SMOKING.
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:
STABLE
NO SHELF LIFE LIMITATIONS FOR COTORAN 80WP. NOT HARMED BY FREEZE-THAW CYCLES /COTORAN 80 WP/
FLUOMETURON IS STABLE IN WATER @ PH VALUES RANGING FROM 1 TO 13 @ 20 DEG C. HALF-LIFE VALUES OF FLUOMETURON AQ SOLN OF PH 5-9 ARE BETWEEN 730 & 1010 DAYS @ TEMP OF 20 DEG C.
... Shelf-life of at least 3 to 5 yr when stored in a dry place and minimum storage temp ... are observed.
... The aqueous stability studies routinely carried out in industrial laboratories indicate that urea herbicides are sufficiently stable under practical temperature and soil conditions to resist hydrolytic breakdown, oxidation, or reduction by ... chemical ... means. /Urea herbicides/
Stable in aqueous acids and alkalis at 20 deg C.
Storage Conditions:
Store in cool, dry, well ventilated, secure area out of reach of children and animals.
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:
For Fluometuron (USEPA/OPP Pesticide Code: 035503) 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./
For control of many broadleaf and grass species.
FLUOMETURON IS ... ESPECIALLY SUITABLE FOR CONTROL OF ANNUAL BROAD-LEAVED AND GRASS WEEDS OF COTTON AT 1.6-2.7 KG ACTIVE INGREDIENT/HECTARE; ALSO AS PRE- AND POST-EMERGENCE SPRAYS ON SUGAR CANE, PINEAPPLE AND COFFEE AT RATES OF 3-4 LB ACTIVE INGREDIENT/ACRE. ... HERBICIDAL PROPERTIES ARE SHARED BY THE 4-TRIFLUOROMETHYL DERIVATIVE BUT NOT BY N'3,5-BIS(TRIFLUOROMETHYL)PHENYL-N,N-DIMETHYLUREA.
Methods of Manufacturing:
REACTION OF PHOSGENE WITH M-TRIFLUOROMETHYLANILINE TO PRODUCE M-TRIFLUOROMETHYLPHENYL ISOCYANATE, FOLLOWED BY REACTION OF THIS WITH DIMETHYLAMINE
Made by the reaction of dimethylamine on 3-trifluoromethylphenyl isocyanate.
m-aminobenzotrifluoride + dimethylcarbonyl chloride (dehydrochlorination)
General Manufacturing Information:
COMPATIBLE WITH OTHER HERBICIDES.
COMBINATION OF ... LOW MAMMALIAN TOXICITY & BIODEGRADABILITY /OF PHENYLUREA HERBICIDES/ LEADS TO CONCLUSION THAT THESE CMPD ARE NOT SIGNIFICANT FACTORS IN CONTAMINATION OF SOIL & WATER SYSTEMS, & THEIR SIGNIFICANCE AS ENVIRONMENTAL POLLUTANTS SEEMS TO BE MINIMAL. /PHENYLUREA HERBICIDES/
Formulations/Preparations:
USEPA/OPP Pesticide Code 035503; Trade Names: Cotoran; C-2059; Lanex; Cottonex.
Fluometuron can be used preplant incorporated at 1.8 kg ai/ha (1.6 lb ai/A) and PRE or POST at 1.12-2.24 kg ai/ha (1-2 kb ai/A) ... It can be applied in water or liquid fertilizer.
50% & 80% WETTABLE POWDERS
TECHNICAL PRODUCT IS ABOUT 96% PURITY.
MAY BE TANK MIXED WITH DISODIUM METHANEARSONATE OR MONOSODIUM METHANEARSONATE FOR DIRECTED POST-EMERGENCE WEED CONTROL IN COTTON.
Cotoran 50 and 80 WP, Wettable powder (500 or 800 g ai/kg); Cotoran 500 FW, suspension concentrate (500 g/l); Cotogard, (fluometuron + prometryn (1:1)); Cotoran multi, (fluometuron + metolachlor (1:1)).
Liquid, dry flowable
Consumption Patterns:
100% AS AN HERBICIDE ON COTTON (1975)
4,500,857 lbs applied on cotton in 1992.
U. S. Production:
(1975) 1.9X10+9 G (CONSUMPTION)
U. S. Imports:
(1976) 5.50X10+8 G (PRINCPL CUSTMS DISTS)
Laboratory Methods:
Analytic Laboratory Methods:
Sample matrix: water-dispersible powders and dusts; suspensions. Assay procedure: IR spectroscopy.
Sample matrix: ... soil. Assay procedure: colorimetry & TLC confirmation.
Sample matrix: ... soil. Assay procedure: GC with ECD.
Sample matrix: plants ... Assay procedure: GC with ECD.
Sample matrix: vegetables, cottonseed, sugar cane ... Assay procedure: colorimetry & TLC confirmation.
Method D4861. Analysis of pesticides and polychlorinated biphenyls in indoor atmospheres. Pesticides and other chemicals are extracted from diethyl ether in hexane and determined by GC coupled with an ECD, nitrogen-phosphorus detector, or a MS. For some pesticides HPLC coupled with UV detector may be preferable. Under the prescribed conditions, fluometuron's estimated detection limit is not determined.
EPA Method 632.Determination of carbamate and urea pesticides in industrial and municipal wastewater using HPLC with UV detector. Approximately 1 liter is solvent extracted with methylene chloride, dried and concentrated to a volume of 10 ml or less. Under the prescribed conditions, for fluometuron the method detection limit is 11.00 ug/l as defined by EPA.
EPA Method IP-8. Determination of organochlorine pesticides in indoor air using GLC coupled with an ECD. Under the prescribed conditions, for fluometuron the method detection limit is 0.20 ug/l as defined by EPA.
Determination of fluometuron in pesticide formulations using GC method with FID. Diethyl phthalate is used as an internal standard solution.
Analysis of products: By HPLC. Analysis of residues: By hydrolysis to the m-trifluoromethylaniline moiety, which is then determined by spectrophotometry or GLC with ECD.
Special References:
Special Reports:
DHEW/NCI; Bioassay of Fluometuron for Possible Carcinogenicity (1980) Technical Rpt Series No. 195 DHEW Pub No. (NIH) 80-1751
Synonyms and Identifiers:
Synonyms:
C 2059
**PEER REVIEWED**
Cotogard
**PEER REVIEWED**
Cotoran
**PEER REVIEWED**
Cotoron
**PEER REVIEWED**
Cottonex
**PEER REVIEWED**
N,N-DIMETHYL-N'-(3-(TRIFLUOROMETHYL)PHENYL)UREA
**PEER REVIEWED**
1,1-Dimethyl-3-(3-trifluoromethylphenyl)urea
**PEER REVIEWED**
1,1-Dimethyl-3-(alpha, alpha, alpha-trifluoro-m-tolyl)urea
**PEER REVIEWED**
Kotoran
**PEER REVIEWED**
Lanex
**PEER REVIEWED**
NCI-C08695
**PEER REVIEWED**
3-(M-TRIFLUOROMETHYLPHENYL)-1,1-DIMETHYLUREA
**PEER REVIEWED**
N-(meta-trifluoromethylphenyl)-N,N'-dimethylurea
**PEER REVIEWED**
N-(3-trifluoromethylphenyl)-N,N'dimethylurea
**PEER REVIEWED**
N-(3-trifluoromethyl)phenyl)-1,1-dimethylurea
**PEER REVIEWED**
3-(3-TRIFLUOROMETHYLPHENYL)-1,1-DIMETHYLUREA
**PEER REVIEWED**
UREA, N,N-DIMETHYL-N'-(3-(TRIFLUOROMETHYL)PHENYL)-
**PEER REVIEWED**
UREA, 1,1-DIMETHYL-3-(ALPHA,ALPHA,ALPHA-TRIFLUORO-M-TOLYL)-
**PEER REVIEWED**Formulations/Preparations:
USEPA/OPP Pesticide Code 035503; Trade Names: Cotoran; C-2059; Lanex; Cottonex.
Fluometuron can be used preplant incorporated at 1.8 kg ai/ha (1.6 lb ai/A) and PRE or POST at 1.12-2.24 kg ai/ha (1-2 kb ai/A) ... It can be applied in water or liquid fertilizer.
50% & 80% WETTABLE POWDERS
TECHNICAL PRODUCT IS ABOUT 96% PURITY.
MAY BE TANK MIXED WITH DISODIUM METHANEARSONATE OR MONOSODIUM METHANEARSONATE FOR DIRECTED POST-EMERGENCE WEED CONTROL IN COTTON.
Cotoran 50 and 80 WP, Wettable powder (500 or 800 g ai/kg); Cotoran 500 FW, suspension concentrate (500 g/l); Cotogard, (fluometuron + prometryn (1:1)); Cotoran multi, (fluometuron + metolachlor (1:1)).
Liquid, dry flowable
Standard Transportation Number:
49 216 87; Phenylurea pesticide, solid, nos
RTECS Number:
NIOSH/YT1575000
Administrative Information:
Hazardous Substances Databank Number: 1721
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, 43 fields added/edited/deleted.
Complete Update on 06/12/2000, 1 field added/edited/deleted.
Complete Update on 03/09/2000, 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 11/18/1999, 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 03/19/1999, 1 field added/edited/deleted.
Complete Update on 03/17/1999, 1 field added/edited/deleted.
Complete Update on 06/02/1998, 1 field added/edited/deleted.
Complete Update on 02/27/1998, 1 field added/edited/deleted.
Complete Update on 11/03/1997, 1 field added/edited/deleted.
Complete Update on 09/17/1997, 1 field added/edited/deleted.
Complete Update on 09/08/1997, 2 fields added/edited/deleted.
Complete Update on 08/11/1997, 2 fields added/edited/deleted.
Complete Update on 04/23/1997, 2 fields added/edited/deleted.
Complete Update on 01/21/1996, 1 field added/edited/deleted.
Complete Update on 08/04/1995, 1 field added/edited/deleted.
Complete Update on 12/28/1994, 1 field added/edited/deleted.
Complete Update on 05/02/1994, 53 fields added/edited/deleted.
Field Update on 03/21/1994, 1 field added/edited/deleted.
Field Update on 09/02/1993, 1 field added/edited/deleted.
Field update on 12/21/1992, 1 field added/edited/deleted.
Complete Update on 09/03/1992, 1 field added/edited/deleted.
Complete Update on 01/23/1992, 1 field added/edited/deleted.
Complete Update on 09/26/1991, 1 field added/edited/deleted.
Complete Update on 10/04/1990, 7 fields added/edited/deleted.
Field Update on 03/06/1990, 1 field added/edited/deleted.
Field Update on 03/01/1989, 1 field added/edited/deleted.
Complete Update on 11/25/1986