Human Health Effects: Human Toxicity Excerpts



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BETANAL


CASRN: 13684-63-4

For other data, click on the Table of Contents
Human Health Effects:
Human Toxicity Excerpts:
Two farmers came separately to the same department of dermatology for diagnosis. One had used phenmedipham for 8 or 9 yr without recognized difficulty in spite of a long history of photodermatitis. However, what was considered an exacerbation of photodermatitis began only a few days after he used phenmedipham in 1978, and a patch test required 14 days to subside. The second farmer presented with a severe, spreading, bullous dermatitis of both hands a few days after he used the compound. He too had used it for 8 or 9 yr without difficulty, but a patch test was positive.

[Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991. 1347]**PEER REVIEWED**



Probable Routes of Human Exposure:
Occupational exposure to betanal occurs through dermal contact and inhalation of sprays, especially to workers applying the compound as a herbicide(1).

[(1) Parmeggiani L; Encyl Occup Health & Safety 3rd ed. Geneva,Switzerland: International Labour Office pp. 1616-46 (1983)]**PEER REVIEWED**



Emergency Medical Treatment:
EMT Copyright Disclaimer:

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The following Overview, *** CARBAMATE HERBICIDES AND FUNGICIDES ***, is relevant for this HSDB record chemical.

Life Support:
o This overview assumes that basic life support measures

have been instituted.



Clinical Effects:
0.2.1 SUMMARY OF EXPOSURE

0.2.1.1 ACUTE EXPOSURE

A) Exposure to these agents does not result in cholinergic

findings. Historically, systemic poisoning by these

agents has been very rare. Reported toxic

manifestations have included CNS depression, seizures,

extrapyramidal effects, neuropathy, and

gastrointestinal effects of nausea, vomiting and

diarrhea.

B) These agents are often compounded with

hydrocarbon-based solvents, which may be responsible

for toxicity.

0.2.5 CARDIOVASCULAR

0.2.5.1 ACUTE EXPOSURE

A) A disulfiram-like reaction (flushing, sweating,

headache, weakness, tachycardia and hypotension) may be

noted when ethanol is ingested following exposure to

large amounts of thiram or possibly MBDT-CARB

compounds.

1) The disulfiram-like reaction following ethanol

ingestion does not appear to occur with the CARB,

T-CARB, or the EBDT-CARB compounds.

0.2.6 RESPIRATORY

0.2.6.1 ACUTE EXPOSURE

A) Respiratory failure, requiring ventilatory support, has

been reported following ingestions.

0.2.7 NEUROLOGIC

0.2.7.1 ACUTE EXPOSURE

A) Exposure to thiram or MBDT-CARB (based on animal

studies) may cause weakness, ataxia, ascending

paralysis and hypothermia.

B) Peripheral neuropathy (pain, numbness and weakness of

the extremities) has been noted following exposure to

thiuram (the ethyl analog of thiram).

0.2.8 GASTROINTESTINAL

0.2.8.1 ACUTE EXPOSURE

A) Nausea, vomiting and diarrhea may occur.

0.2.10 GENITOURINARY

0.2.10.1 ACUTE EXPOSURE

A) Two cases of renal failure following maneb exposure

have been reported in Japan.

0.2.14 DERMATOLOGIC

0.2.14.1 ACUTE EXPOSURE

A) Exposure to dusts, sprays, solutions, wettable powder

suspensions or emulsions of these agents may lead to

skin and mucous membrane irritation.

0.2.20 REPRODUCTIVE HAZARDS

A) No adverse reproductive effects (testicular parameters)

in male mice were observed following methyl thiophanate

doses up to 1000 mg/kg orally for 5 consecutive days

(Traina et al, 1998). Maternal toxicity was evident in

female rats.

0.2.21 CARCINOGENICITY

0.2.21.1 IARC CATEGORY

A) IARC Carcinogenicity Ratings for CAS137-26-8 (IARC,

2004):


1) IARC Classification

a) Listed as: Thiram

b) Carcinogen Rating: 3

1) The agent (mixture or exposure circumstance) is not

classifiable as to its carcinogenicity to humans.

This category is used most commonly for agents,

mixtures and exposure circumstances for which the

evidence of carcinogenicity is inadequate in humans

and inadequate or limited in experimental animals.

Exceptionally, agents (mixtures) for which the

evidence of carcinogenicity is inadequate in humans

but sufficient in experimental animals may be placed

in this category when there is strong evidence that

the mechanism of carcinogenicity in experimental

animals does not operate in humans. Agents, mixtures

and exposure circumstances that do not fall into any

other group are also placed in this category.

0.2.22 GENOTOXICITY

A) Neither PROPOXUR nor DITHANE M-45 was clastogenic in

mice (Vasudev & Krishnamurthy, 1994).

B) ETU is not believed to be genotoxic to mammals (Elia et

al, 1995).



Laboratory:
A) Blood levels are not clinically useful.

B) No specific laboratory work (CBC, electrolytes,

urinalysis) is needed unless otherwise indicated, ie,

severe vomiting and diarrhea, etc.



Treatment Overview:
0.4.2 ORAL EXPOSURE

A) EMESIS: Ipecac-induced emesis is not recommended because

of the potential for CNS depression and seizures.

B) ACTIVATED CHARCOAL: Administer charcoal as a 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.

C) 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.

D) INTRAVENOUS FLUIDS may be useful in restoring

extracellular fluid volume following severe vomiting and

diarrhea.

E) OXYGEN THERAPY is effective in relieving the distress of

ANTABUSE-LIKE REACTIONS rarely associated with exposure

to thiram and possibly the MBDT-CARB compounds.

F) NO SPECIFIC ANTIDOTES ARE AVAILABLE for poisoning by

these compounds.

G) ACTIVATED CHARCOAL: Administer charcoal as a 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.

0.4.3 INHALATION EXPOSURE

A) 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 inhaled

beta2 agonist and oral or parenteral corticosteroids.

0.4.5 DERMAL EXPOSURE

A) OVERVIEW

1) DECONTAMINATION: Remove contaminated clothing and wash

exposed area thoroughly with soap and water. A

physician may need to examine the area if irritation or

pain persists.



Range of Toxicity:
A) Persons sensitive to thiram may develop dermal reactions

following minimal exposure. With this exception, systemic

toxicity of these compounds is generally low.

B) LD50 values range from 400 mg/kg (nabam and diallate) to

34,000 mg/kg for terbucarb.
[Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2004; CCIS Volume 122, edition expires Nov, 2004. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2004; CCIS Volume 122, edition expires Nov, 2004.]**PEER REVIEWED**

Antidote and Emergency Treatment:
Treatment /of phenmedipham poisoning/ is symptomatic.

[Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991. 1347]**PEER REVIEWED**



Animal Toxicity Studies:

Non-Human Toxicity Excerpts:
FOUR MO FEEDING STUDIES ON RATS SHOWED NO PATHOLOGICAL CHANGES WHEN PHENMEDIPHAM WAS FED AT RATE OF 500 MG/KG OF BODY WT. REDN IN BODY WT ... FOUND TO BE DUE TO LACK OF PALATABILITY OF FEED CONTAINING PHENMEDIPHAM. AFTER 4 WK, NO CUMULATIVE EFFECTS WERE OBSERVED IN RATS FED DAILY DOSES OF 5X1000 MG/KG PHENMEDIPHAM.

[Weed Science Society of America. Herbicide Handbook. 4th ed. Champaign, IL: Weed Science Society of America, 1979. of America, 1979. 331]**PEER REVIEWED**


A TWO YEAR ONCOGNOCITY STUDY ON RAT SHOWED NO HISTOMORPHOLOGIC ALTERATIONS AT DIETARY LEVELS OF 500 PPM AND LESS. A TWO YEAR DOG FEEDING STUDY SHOWED NO CMPD RELATED EFFECTS AT DIETARY LEVELS OF 1000 PPM AND LESS.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 377]**PEER REVIEWED**


... TOXICITY TO ... RAINBOW TROUT: SOME TOXIC SYMPTOMS AT 0.01 ML OF PHENMEDIPHAM/L OF WATER; LETHAL CONCN: 0.02 ML OF PHENMEDIPHAM/L.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 377]**PEER REVIEWED**


Betanal was embryotoxic when administered to rats during pregnancy by the oral route and via inhalation. Its teratogenic and embryotoxic effects in the pregnant animals decreased with reduction in the dose of the herbicide. Single and repeated administration of betanal increased the RNA in the liver of pregnant females and the placenta. A substantial decrease was noted in the liver and moderate decrease in the myocardium of the embryo. DNA increased in both liver and myocardium of the embryo by 36% and 49%, respectively; analogous changes were observed in the placenta. The pregnant rats exposed to betanal showed increased RNA. Embryotoxic and teratogenic effects of betanal play a major role in disrupting the nucleic acid metabolism. The threshold concn of betanal, considering its embryotoxic effects, is 2 mg/cu m.

[Medved IL; Gig Sanit (4): 16-8 (1984)]**PEER REVIEWED**


Rats fed at rates of 125, 250, and 500 mg/kg/day for 120 days survived, but food intake was decreased in a dosage-dependent way.

[Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991. 1347]**PEER REVIEWED**



Non-Human Toxicity Values:
LD50 Dog oral 4000 mg/kg

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


LD50 Guinea pig oral 4000 mg/kg

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


LD50 Chicken oral 3000 mg/kg

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


LD50 Rat percutaneous 4000 mg/kg

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


LD50 Rat oral >8000 mg/kg

[Sittig, M. (ed.) Pesticide Manufacturing and Toxic Materials Control Encyclopedia. Park Ridge, NJ: Noyes Data Corporation. 1980. 605]**PEER REVIEWED**



Ecotoxicity Values:
LC50 Harlequin fish 16.5 mg/l/96 hr /Conditions of bioassay not specified/ /emulsifiable preparation/

[Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A319/Oct 87]**PEER REVIEWED**



Metabolism/Pharmacokinetics:

Metabolism/Metabolites:
WHEN ADMIN TO WHITE RATS, PHENMEDIPHAM ... RAPIDLY METABOLIZED ... HYDROLYSIS YIELDED METHYL N-(3-HYDROXYPHENOL) CARBAMATE (MHPC) ... HYDROXYPHENYLCARBAMATES FORMED ... DEGRADED TO M-AMINOPHENOL WHICH WAS ACETYLATED TO ... 3-HYDROXYACETANILIDE. THESE METABOLITES WERE THEN CONJUGATED AS GLUCURONIDES & SULFATES.

[Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974. 290]**PEER REVIEWED**


BETANAL ... WAS RAPIDLY METABOLIZED BY RATS TO CORRESPONDING PHENOL ... (60-70%)(WHICH WAS PARTLY CONJUGATED) & M-HYDROXYANILINE, WHICH WAS EXCRETED AS M-HYDROXYACETANILIDE ... (2%).

[The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975. 418]**PEER REVIEWED**



Absorption, Distribution & Excretion:
In rats, dogs & humans ... phenmedipham ... /is/ readily absorbed ... .

[Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-327]**PEER REVIEWED**


RECOVERY OF /ORALLY/ ADMIN DOSE /TO RATS/ IN URINE & FECES, AT 72 HR AFTER TREATMENT, WAS ... 99% ... URINE ... PRIMARY ROUTE OF ELIMINATION, WITH 80% ... EXCRETED VIA URINE IN INITIAL 24 HR ... TRACE AMT OF RADIOLABEL ... IN KIDNEY ... 0.039 PPM ... ALL OTHER TISSUES FELL BELOW THIS LEVEL.

[Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975. 648]**PEER REVIEWED**


It is absorbed through leaves & has little action by way of soil & roots.

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**



Mechanism of Action:
BETANAL EXERTS ITS HERBICIDAL ACTION BY DISRUPTING PHOTOCHEMICAL REACTIONS. MAJOR CHANGES INVOLVED PHOSPHORYLATION & ITS RELATED NONCYCLIC ELECTRON TRANSPORT.

[LAPINA TV, KHODEEVA V; MEKH DEISTVIYA GERBITS SINT REGUL ROSTA RAST IKH SUD'BA BIOSFERE MATER MEZHDUNAR SIMP STRAN 1: 82-6 (1975)]**PEER REVIEWED**


PHENMEDIPHAM IS STRONG INHIBITOR OF HILL REACTION /IN PLANTS/.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 377]**PEER REVIEWED**


At concn near 2X10-4 M, phenmedipham inhibited electron transfer in potato and mung bean mitochondria. The inhibition seemed to be localized in the flavoprotein region. It affected preferentially the exogenous nicotinamide-adenine dinucleotide (NADH) dehydrogenase, in potato mitochondria. Succinate dehydrogenase was less inhibited. Photosynthesis was completely inhibited by 2X10-7 M phenmedipham.

[Macherel D et al; Pestic Biochem Physiol 18 (3): 280-8 (1982)]**PEER REVIEWED**



Pharmacology:

Environmental Fate & Exposure:

Environmental Fate/Exposure Summary:
Betanal's use as a post-emergence herbicide releases the compound directly to the environment through applications in sprays, concentrates and other routes of application. If released to the atmosphere, betanal will degrade rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals (half-life of about 2.6 hr). Particulate-phase betanal and aerosols released to air during applications of betanal herbicides will be removed from air physically by dry and wet deposition. If released to soil or water, betanal can degrade through biodegradation and aqueous hydrolysis. The hydrolysis rate increases with increasing pH; at 25 deg C, the hydrolysis half-life is about 7.5 days, 18 hr, and 1.8 hr at respective pHs of 6, 7, and 8. Betanal is reported to remain in the top layers of soil (0 to 2 inches) after herbicidal application and has a high Koc value suggesting a low potential to leach. The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 30 days for betanal; however, the rate could be slower in acidic soil or faster in alkaline soil. Occupational exposure to betanal occurs through dermal contact and inhalation of sprays, especially to workers applying the compound as a herbicide. (SRC)

**PEER REVIEWED**



Probable Routes of Human Exposure:
Occupational exposure to betanal occurs through dermal contact and inhalation of sprays, especially to workers applying the compound as a herbicide(1).

[(1) Parmeggiani L; Encyl Occup Health & Safety 3rd ed. Geneva,Switzerland: International Labour Office pp. 1616-46 (1983)]**PEER REVIEWED**



Artificial Pollution Sources:
Betanal's use as a post-emergence herbicide(1-2) releases the compound directly to the environment through applications in sprays, concentrates and other routes of application(SRC).

[(1) Worthing CR, Walker SB; The Pesticide Manual 8th ed.; Lavenham Suffolk, England: Lavenham Press Ltd p. 652 (1987) (2) Hartley D, Kidd H; The Agrochemicals Handbook. Nottingham,England: The Royal Society of Chemistry (1985)]**PEER REVIEWED**



Environmental Fate:
In soils, 71-86% of amount determined 1 day after treatment was degraded in 90 days.

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


TERRESTRIAL FATE: Betanal can degrade in soil through microbial degradation and chemical hydrolysis. Biological screening studies have demonstrated that betanal will biodegrade(1-2); in one study, chemical degradation was faster than microbial degradation(2). Betanal is susceptible to alkaline hydrolysis. The following aqueous hydrolysis half-lives have been reported for buffered betanal solutions at 22 deg C(3): 70 days at pH 5, 24 hr at pH 7 and 10 min at pH 9(3). The second-order hydrolysis rate constant was experimentally determined to be 106 L/mol-sec at 25 deg C(4) which corresponds to half-lives of 7.5 days at pH 6, 18 hr at pH 7 and 1.8 hr at pH 8(4,SRC). Therefore, degradation rates can be expected to increase with increasing pH; microbial degradation will become more important as the acidity increases(SRC).

[(1) Fuka T, Pitter P; Vodni Hospod 34: 205-9 (1984) (2) Knowles CO, Benezet HJ;Bull Environ Contam Toxicol 27: 529-33 (1981) (3) Worthing CR, Walker SB; The Pesticide Manual 8th ed.; Lavenham Suffolk,England: Lavenham Press Ltd p. 652 (1987) (4) Bergon M et al; J Agric Food Chem 33: 577-83 (1985)]**PEER REVIEWED**


TERRESTRIAL FATE: The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 30 days for betanal(1). At recommended application rates, the resultant avg persistence is reported to be 25 days(4). In slightly acidic soils of low humus content, half-lives of 28-55 days were observed(2). Using an alkaline soil (pH 8) and C14-labelled betanal, the concn of betanal dropped from 89.6% at time zero to approximately 11% in 32 days(3); methyl hydroxyphenylcarbamate was the major metabolite with small amounts of m-aminophenol(3). Betanal is reported to remain in the top layers of soil (0 to 2 inches) after herbicidal applications(4) and its Koc value of 2400(1) would suggest a low potential to leach(SRC).

[(1) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991) (2) Kossmann K; Weed Res; 10: 349 (1970) (3) Sonawane BR; Knowles CO; Bull Environ Contam Toxicol 6: 322-7 (1971) (4) WSSA; Herbicide Handbook of the Weed Science Society of America 6th ed. Champaign,IL pp. 208-9 (1989)]**PEER REVIEWED**


AQUATIC FATE: Betanal can degrade in water through microbial degradation and chemical hydrolysis. Biological screening studies have demonstrated that betanal will biodegrade(1-2). Betanal is susceptible to alkaline hydrolysis. The following aqueous hydrolysis half-lives have been reported for buffered betanal solutions at 22 deg C(3): 70 days at pH 5, 24 hr at pH 7 and 10 min at pH 9(3). The second-order alkaline hydrolysis rate constant was experimentally determined to be 106 L/mol-sec at 25 deg C(4) which corresponds to half-lives of 7.5 days at pH 6, 18 hr at pH 7 and 1.8 hr at pH 8(4,SRC). Therefore, degradation rates in water may increase with increasing pH; microbial degradation may become more important as the acidity increases(SRC). Based upon a Koc value of 2400(5), some partitioning from the water column to sediment and suspended material may occur(SRC). Aquatic volatilization is not expected to be important fate process(SRC).

[(1) Fuka T, Pitter P; Vodni Hospod 34: 205-9 (1984) (2) Knowles CO, Benezet HJ;Bull Environ Contam Toxicol 27: 529-33 (1981) (3) Worthing CR, Walker SB; The Pesticide Manual 8th ed.; Lavenham Suffolk,England: Lavenham Press Ltd p. 652 (1987) (4) Bergon M et al; J Agric Food Chem 33: 577-83 (1985) (5) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991)]**PEER REVIEWED**


ATMOSPHERIC FATE: Based upon a reported vapor pressure of 1X10-11 mm Hg at 25 deg C(1), betanal can exist in both the vapor and particulate phases in the ambient atmosphere, although the particulate phase may dominate(2,SRC). It will degrade rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 2.6 hr(3,SRC). Particulate phase betanal and aerosols released to air during applications of betanal herbicides will be physically removed from air dry and wet deposition(SRC).

[(1) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991) (2) BidlemanTF; Environ Sci Technol 22: 361-7 (1988) (3) Meylan WM, Howard PH; Chemosphere 26: 2293-9 (1993) (4) Nations BK, Hallberg GR; J Environ Qual 21: 486-92 (1992)]**PEER REVIEWED**


The mineralization of phenmedipham in soil (control) and in soil amended with compost during a 1 yr incubation depended on compost type. It was highest during the entire year when straw compost was added and only slightly higher than in the control when the soil was amended with compost from mushroom bed (2nd highest), oak bark-hen manure mixture, and grape residues. During the 1st wk, the mineralization rate in soil treated with the bark-hen manure compost was lower than in the control soil, but slightly increased over that in the soil alone after the 1st mo of incubation. The maximum rate of herbicide degradation by the soil amended with straw compost (176% of the control) was observed after the 1st month of incubation; at the year end the degradation was 128% of the control for the straw compost but only 101.5-102% for the other composts. The (14)CO2 released was 37.6% for straw compost and 29.4% for the control. Of the residual (14)C, 74.4 and 73.3%, resp, were found in humates + fulvates. Other than straw, composts resulted in higher incorporations of residual (14)C in the humic substances (79.6-89.5%). The total of (14)CO2 + (14)C in the humic substances was 81.2% in control soil, 84.3% for straw compost, 85.7% for grape compost and 90.5 and 92.6% for the mushroom bed and bark-hen manure compost, resp. The free (14)C constituted 39.2-83.9% of that in the control (100%), being lowest for the bark-manure and highest for the straw compost.

[Bellinck C, Mayaudon J; Effect of Some Composts on the Mineralization of (14)C-Phenmedipham in a Fresh Meadow Soil and the Immobilization of the Carbon-14 Labeled Residues. Rev Ecol Biol Sol 20 (3): 291-7 (1983)]**PEER REVIEWED**


Nitrogen and nitrogen-phosphorous-potassium fertilizers (ammonium sulfate, calcium phosphate, and potassium sulfate), glucose, cellulose, and amorphous calcic humates had a positive effect on the mineralization of (14)C-labeled phenmedipham in the fresh meadow soil. All amendments tested increased the quantity of (14)C substances fixed on soil constituents and so decreased pollution. The quantity of free (14)C in the soil after a 1 yr incubation with the various amendments ranged 56-93% of that of the control.

[Bellinck C; Effect of Some Amendments on the Mineralization of (14)C Phenmedipham in a Fresh Meadow Soil and the Immobilization of the (14)C Labeled Residues. Rev Ecol Biol Sol 20 (2): 155-63 (1983)]**PEER REVIEWED**


Soil pH influences the sequence of phenmedipham degradation: in an acid soil, degradation starts by a dealkylation followed by a cleavage of the aromatic ring disposed between the 2 carbamoyl linkages and ends by the degradation of the 2nd benzene ring; in a neutral soil the sequence of degradation of the 2 rings is inversed. The (14)C phenmedipham and its (14)C residues obtained after 1 yr incubation are much stronger adsorbed on the humic-clay complexes of the neutral soil than on those of the acid soil. Soil pollution by the toluidine molecule in acid soil is 4 fold that in neutral medium. This necessitates the adjustment of the amount of pesticide used to treat different types of soils depending on their acidity.

[Bellinck C, Mayaudon J; Effect of Acidity on Mineralization of Phenmedipham in Soil. Rev Ecol Biol Sol 20 (1): 23-8 (1983)]**PEER REVIEWED**


Phenmedipham and lenacil, at 40 ppm air-dry soil, were incubated at 90% field water capactity @ 20 deg. The half-lives were 39 and 108 days, respectively. Lenacil was more persistent in alkaline than in acid soils, with half-life of 138 and 78 days, respectively. In the acid soils, persistence was markedly increased by combining with phenmedipham (half-life 127 days). In alkaline soil, the persistence of thecombination was similar to, or less than, that of lenacil alone.

[Tena M et al; Soil Persistence of Selected Sugar-beet Herbicides and Their Combinations with Lenacil. Weed Res 22 (5): 245-9 (1982)]**PEER REVIEWED**



Environmental Biodegradation:
In slightly acid soil of low humus content, phenmedipham decomposed with a half-life of 28 to 55 days.

[Menzie, C.M. Metabolism of Pesticides, Update II. U.S. Department of the Interior, Fish Wildlife Service, Special Scientific Report - Wildlife No. 2l2. Washington, DC: U.S. Government Printing Office, 1978.222]**PEER REVIEWED**


Using an activated sludge inoculum, betanal had a 5-day theoretical BOD of 52.3%(1). Betanal was found to be very susceptible to microbial attack by a variety of microorganisms isolated from soil(2); in 28-day incubation studies, only 0.6% (or less) of initial betanal remained when the microbes were present while 29.8% remained in the control tests(2); methyl-N-(3-hydroxyphenyl) carbamate was the major degradation product(2).

[(1) Fuka T, Pitter P; Vodni Hospod 34: 205-9 (1984) (2) Knowles CO, Benezet HJ; Bull Environ Contam Toxicol 27: 529-33 (1981)]**PEER REVIEWED**



Environmental Abiotic Degradation:
The rate constant for the vapor phase reaction of betanal with photochemically produced hydroxyl radicals has been estimated to be 1.91X10-10 cu cm/molecule-sec at 25 deg C which corresponds to an atmospheric half-life of about 2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The following aqueous hydrolysis half-lives have been reported for buffered betanal solutions at 22 deg C(2); 70 days at pH 5, 24 hr at pH 7 and 10 min at pH 9(2). The second-order alkaline hydrolysis rate constant was experimentally determined to be 106 L/mol-sec at 25 deg C(3) which corresponds to halves-life of 7.5 days at pH 6, 18 hr at pH 7 and 1.8 hr at pH 8(3,SRC); the hydrolysis products include methyl N-3(hydroxyphenyl) carbamate and m-toluidine via N-(m-tolyl)carbamic acid(3). Betanal absorbs UV light in the environmental solar spectrum(4); therefore, photodegradation may have some importance in the environment(SRC).

[(1) Meylan WM, Howard PH; Chemosphere 26: 2293-9 (1993) (2) Worthing CR, Walker SB; The Pesticide Manual 8th ed.; Lavenham Suffolk, England: Lavenham Press Ltd p. 652 (1987) (3) Bergon M et al; J Agric Food Chem 33: 577-83 (1985) (4) Meallier P et al; Chemosphere 16: 513-7 (1987)]**PEER REVIEWED**



Environmental Bioconcentration:
Based upon a water solubility of 4.7 mg/L at 25 deg C(1), the BCF of betanal can be estimated to be 260 from a regression derived equations(2,SRC). This BCF value suggests that bioconcentration in aquatic organisms may occur(SRC).

[(1) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991) (2) Lyman WJet al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc p. 5-10 (1990)]**PEER REVIEWED**



Soil Adsorption/Mobility:
Molecular modelling techniques used to estimate the mobility of organic chemicals in soils were evaluated. The effect of molecular structure & water solubility on mobility is discussed.

[Dragun J, Helling CS; Evaluation of molecular modelling techniques to estimate the mobility of organic chemicals in soils: II. Water solubility and the molecular fragment mobility coefficient; US Environ Prot Agency, Off Res Dev, EPA (EPA-600/9-81-0026, Land Disposal: Hazardous Waste, Proc Annu Res, 7th, PB81-173882): 58-70 (1981)]**PEER REVIEWED**


Using several different soils, an Rf value of 0.17 was measured via soil thin-layer chromatography which is indicative of low soil mobility(1). Based upon a water solubility of 4.7 mg/L at 25 deg C(2), the Koc of betanal can be estimated to be about 1860 from a regression derived equation(3,SRC). The US Dept Agric's Pesticide Properties Database lists a Koc value of 2400 for betanal(2). According to a suggested classification scheme(4), these Koc values suggest that betanal has low mobility in soil(SRC). Betanal is reported to remain in the top layers of soil (0 to 2 inches) after herbicidal application(5). In a field study in sugar beet soil, applications of betanal remained in the upper 10 cm of soil 2 months after application(6).

[(1) Helling CS et al; Phytopathology 64: 1091-1100 (1974) (2) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods Washington,DC: Amer Chem Soc p. 4-9 (1990) (4) Swann RL et al; Res Rev 85: 23 (1983) (5) WSSA; Herbicide Handbook of the Weed Science Society of America 6th ed. Champaign,IL pp. 208-9 (1989) (6) Bidnenko LI; Khim Sel'sk Khoz 16: 77-8 (1978)]**PEER REVIEWED**



Volatilization from Water/Soil:
Based upon a vapor pressure of 1.0X10-11 mm Hg(1 and a water solubility of 4.7 mg/L at 25 deg C(1), the Henry's Law constant for betanal can be estimated to be 8.41X10-13 atm-cu m/mole(SRC). This value of Henry's Law constant indicates that betanal is essentially nonvolatile from water(3).

[(1) Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991) (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington,DC: Amer Chem Soc pp. 15-15 to 15-29 (1990)]**PEER REVIEWED**



Environmental Water Concentrations:
SURFACE WATER: Betanal has been qualitatively detected in lowland river waters collected in Britain and West Germany (concns, dates, sites not reported)(1).

[(1) Crathorne B et al; Environ Sci Technol 18: 797-802 (1984)]**PEER REVIEWED**


GROUNDWATER: During various sampling periods in 1984, water samples were collected from 206 waterwork wells in Germany and analyzed from 35 different pesticides(1); betanal was not detected above a detection limit of 0.05 ug/L(1).

[(1) Iwan VJ; Gesunde Pflanz 40: 208-13 (1988)]**PEER REVIEWED**



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. Phenmedipham 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: 0277; Pesticide type: Herbicide; Registration Standard Date: 03/30/87; 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): Phenmedipham; Data Call-in (DCI) Date(s): 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.

[USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.141 (Spring, 1998) EPA 738-R-98-002]**QC REVIEWED**


Tolerances are established for residues of the herbicide phenmedipham, methyl m-hydroxycarbanilate m-methylcarbanilate in or on the following raw agricultural commodities: beets, beets (sugar, roots and tops), and spinach.

[40 CFR 180.278 (7/1/92)]**PEER REVIEWED**



Allowable Tolerances:
Tolerances are established for residues of the herbicide phenmedipham, methyl m-hydroxycarbanilate m-methylcarbanilate in or on the following raw agricultural commodities: beets, 0.2 ppm (negligible residue (N)); beets (sugar, roots and tops), 0.1 ppm (N); and spinach, 0.5 ppm.

[40 CFR 180.278 (7/1/92)]**PEER REVIEWED**



Chemical/Physical Properties:

Molecular Formula:
C16-H16-N2-O4

**PEER REVIEWED**



Molecular Weight:
300.3

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**



Color/Form:
Colorless crystals

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**



Odor:
ODORLESS

[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982. 448]**PEER REVIEWED**



Melting Point:
139-142 (143-144 DEG C)

[Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 1149]**PEER REVIEWED**



Corrosivity:
Non-corrosive

[Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A319/Aug 87]**PEER REVIEWED**



Density/Specific Gravity:
0.25-0.30 g/cu c at 20 deg C

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**



Solubilities:
4.7 MG/L WATER; ABOUT 200 G/KG IN ACETONE, CYCLOHEXANONE; ABOUT 50 G/KG IN METHANOL; 20 G/KG IN CHLOROFORM; 2.5 G/KG IN BENZENE; ABOUT 500 MG/KG IN HEXENE AT ROOM TEMP

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**



Spectral Properties:
Intense mass spectral peaks: 167 m/z (100%), 133 m/z (96%), 135 m/z (64%), 104 m/z (53%)

[Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton, FL: CRC Press Inc., 1985. 218]**PEER REVIEWED**



Vapor Pressure:
1.3 nPa at 25 deg C

[Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A319/Aug 87]**PEER REVIEWED**



Other Chemical/Physical Properties:
COLORLESS, ODORLESS, CRYSTALLINE SOLID; MP 143-144 DEG C; SOLUBILITY: 1 MG/L WATER AT 20 DEG C, ACETONE 20%, CYCLOHEXANONE 20%, METHANOL 5% /TECHNICAL MATERIAL 97% PURE/

[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982. 448]**PEER REVIEWED**


Henry's Law constant= 8.41X10-13 atm-cu m/mole (est)

[SRC]**PEER REVIEWED**



Chemical Safety & Handling:

Flash Point:
74 DEG C CC

[Weed Science Society of America. Herbicide Handbook 3rd ed. Champaign, Illinois: Weed Science Society of America, 1974. 340]**PEER REVIEWED**



Protective Equipment & Clothing:
Wear goggles to prevent splashing into eyes.

[Farm Chemicals Handbook 1992. Willoughby, OH: Meister Publishing Co., 1992.,p. C-259]**PEER REVIEWED**



Preventive Measures:
DO NOT BREATHE SPRAY MIST. DO NOT EAT, DRINK, OR SMOKE WHILE SPRAYING.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 376]**PEER REVIEWED**



Stability/Shelf Life:
VERY LOW VOLATILITY; NO CHANGES WERE OBSERVED WHEN HELD FOR 6 DAYS AT 50 DEG C; HYDROLYSIS AT 22 DEG C IN BUFFER SOLN, 50% LOSS OCCURRED IN 70 DAYS AT PH 5, 24 HR AT PH 7, 10 MIN AT PH 9.

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


SHELF LIFE OVER 1 YR

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 376]**PEER REVIEWED**



Occupational Exposure Standards:

Manufacturing/Use Information:

Major Uses:
POST EMERGENT HERBICIDE FOR CONTROL OF CERTAIN BROADLEAF & GRASS WEEDS; RECOMMENDED FOR USE IN SUGAR BEETS, STRAWBERRIES & SUNFLOWERS

[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982. 448]**PEER REVIEWED**



Manufacturers:
Kemira Oy, PO Box 330, Porkkalankatu 3, SF-00101 Helsinki, Finland, 358-0-13211

[Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C 263]**PEER REVIEWED**


Pen-Tsao-Materia-Medica-Center GmbH, Bergstr 11, 2000 Hamburg, Germany, 40-32-1328

[Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C 263]**PEER REVIEWED**


Schering AG, Agrochemical Div, PO Box 65 03 11, 1000 Berlin 65, Germany, 030-468-0

[Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C 263]**PEER REVIEWED**



Methods of Manufacturing:
PRODUCED BY REACTION OF 3-METHOXYCARBONYLAMINOPHENOL & M-TOLYL ISOCYANATE ... .

[Worthing, C. R. (ed.). Pesticide Manual. 6th ed. Worcestershire, England: British Crop Protection Council, l979. 413]**PEER REVIEWED**



General Manufacturing Information:
US PATENT/S/ 3,404,075 & 3,692,820.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 378]**PEER REVIEWED**


IT IS APPLIED EITHER BROADCAST OR AS BAND TREATMENT. RATES: BROADCAST--1 TO 1.25 LB/ACRE AT COTYLEDON TO TWO TRUE LEAF STAGE WEEDS. 1.25 TO 1.5 LB/ACRE AT 2 TO 4 TRUE LEAF STAGE OF WEEDS. USUAL CARRIER: PHENMEDIPHAM IS APPLIED DILUTED WITH WATER AT BROADCAST RATE OF 20 GALLONS/ACRE.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 376]**PEER REVIEWED**



Formulations/Preparations:
'BETANAL' (157 G AI/L); IN UNITED KINGDOM 'BETANAL E' (120 G/L). TECHNICAL PRODUCT IS MORE THAN 95% PURE.

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


EMULSIFIABLE CONCENTRATES 16.7% (WT/VOL) TECHNICAL MATERIAL, 15.9% (WT/VOL) TECHNICAL MATERIAL.

[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982. 448]**PEER REVIEWED**



Laboratory Methods:

Analytic Laboratory Methods:
ACTIVE INGREDIENT IN BETANAL IS DETERMINED BY HYDROLYSIS & STEAM DISTILLATION FOLLOWED BY BROMOMETRIC TITRATION.

[Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983. 378]**PEER REVIEWED**


The use of coupled-column HPLC and MS using field desorption and fast atom bombardment ionization for the separation and identification of organics isolated from river and drinking water was reported. Phenmedipham was identified in river water using field desorption MS.

[Crathorne B et al; Environ Sci Technol 18 (10): 797-802 (1984)]**PEER REVIEWED**


The adsorption properties of Tenax were studied to test the possibility of concentration and recovery of pollutant substances. Pesticides of various classes (chlorinated, phosphorated, carbamates, carbonates) and other organic toxicants having different volatility were employed as substances to be concentrated. They were present in water at 0.1 ppb. Recovery was made by solvent extraction or by thermoelution. Revelation and quantitative analysis were performed by GC and by high pressure TLC.

[Agostiano A et al; Water Air Soil Pollut 19 (4): 309-20 (1983)]**PEER REVIEWED**


Simultaneous determination of several carbamate pesticides including betanal in fruits and vegetables by multistage HPLC in a single run.

[Fogy I et al; Z Lebensm-Unters -Forsch 173 (4): 268-74 (1981)]**PEER REVIEWED**



Special References:

Synonyms and Identifiers:

Synonyms:
CARBAMIC ACID, (3-METHYLPHENYL)-, 3-((METHOXYCARBONYL)AMINO)PHENYL ESTER

**PEER REVIEWED**


CARBANILIC ACID, M-HYDROXY, METHYL ESTER, M-METHYLCARBANILATE (ESTER)

**PEER REVIEWED**


3-(CARBOMETHOXYAMINO)PHENYL 3-METHYLCARBANILATE

**PEER REVIEWED**


EP-452

**PEER REVIEWED**


FENMEDIFAM

**PEER REVIEWED**


KEMIFAM

**PEER REVIEWED**


3-METHOXYCARBONYLAMINOPHENYL N-3'-METHYLPHENYLCARBAMATE

**PEER REVIEWED**


METHYL M-HYDROXYCARBANILATE, M-METHYLCARBANILATE

**PEER REVIEWED**


METHYL-3-HYDROXYCARBANILATE-3-METHYLCARBANILATE

**PEER REVIEWED**


METHYL N-(3-(N-(3-METHYLPHENYL)CARBAMOYLOXY)PHENYL)CARBAMATE

**PEER REVIEWED**


METHYL-3-M-TOLYCARBAMOLOXYPHENYL CARBAMATE

**PEER REVIEWED**


PHENMEDIPHAM

**PEER REVIEWED**


SCHERING-38584

**PEER REVIEWED**


SN-38584

**PEER REVIEWED**


SN 4075

**PEER REVIEWED**


SPIN-AID

**PEER REVIEWED**



Formulations/Preparations:
'BETANAL' (157 G AI/L); IN UNITED KINGDOM 'BETANAL E' (120 G/L). TECHNICAL PRODUCT IS MORE THAN 95% PURE.

[Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987. 652]**PEER REVIEWED**


EMULSIFIABLE CONCENTRATES 16.7% (WT/VOL) TECHNICAL MATERIAL, 15.9% (WT/VOL) TECHNICAL MATERIAL.

[Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982. 448]**PEER REVIEWED**



Administrative Information:

Hazardous Substances Databank Number: 1402
Last Revision Date: 20030214
Last Review Date: Reviewed by SRP on 3/2/1994
Update History:
Complete Update on 02/14/2003, 1 field added/edited/deleted.

Complete Update on 01/14/2002, 1 field added/edited/deleted.

Complete Update on 08/09/2001, 1 field added/edited/deleted.

Complete Update on 04/20/2000, 1 field added/edited/deleted.

Complete Update on 03/09/2000, 1 field added/edited/deleted.

Complete Update on 02/09/2000, 1 field added/edited/deleted.

Complete Update on 02/02/2000, 1 field added/edited/deleted.

Complete Update on 12/27/1999, 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 06/02/1998, 1 field added/edited/deleted.

Complete Update on 10/23/1997, 1 field added/edited/deleted.

Complete Update on 09/17/1997, 1 field added/edited/deleted.

Complete Update on 05/08/1997, 1 field added/edited/deleted.

Complete Update on 04/07/1997, 1 field added/edited/deleted.

Complete Update on 10/13/1996, 1 field added/edited/deleted.

Complete Update on 01/21/1996, 1 field added/edited/deleted.

Complete Update on 05/26/1995, 1 field added/edited/deleted.

Complete Update on 12/28/1994, 1 field added/edited/deleted.

Complete Update on 05/18/1994, 41 fields added/edited/deleted.

Field Update on 03/21/1994, 1 field added/edited/deleted.

Complete Update on 02/05/1993, 1 field added/edited/deleted.

Field update on 12/20/1992, 1 field added/edited/deleted.

Field update on 12/29/1989, 1 field added/edited/deleted.



Complete Update on 04/30/1986


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