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TRIADIMEFONCASRN: 43121-43-3For other data, click on the Table of Contents

Human Health Effects:

Human Toxicity Excerpts:

Overexposures of humans are said to have resulted in hyperactivity followed by sedation. [U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: http://www.epa.gov/pesticides/safety/healthcare 154]**PEER REVIEWED**

Skin, Eye and Respiratory Irritations:

It causes irritation if eyes are contaminated. [U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: http://www.epa.gov/pesticides/safety/healthcare 154]**PEER REVIEWED**

Probable Routes of Human Exposure:

Occupational exposure to triadimefon occurs through dermal contact and inhalation of sprays, especially to workers applying the compound as a pesticide(1). Dermal exposure to triadimefon is reported to occur in tree nursery workers who handle triadimefon pesticides(2). Since triadimefon has been detected occasionally in the U.S. foods (3), limited exposure to the general population may occur through consumption of foods containing triadimefon residues (SRC). [(1) Parmeggiani L; Encycl Occup Health and Safety 3rd ed. Geneva, Switzerland: International Labor Office pp. 1616-46 (1983) (2) Lavy TL et al; Arch Environ Contam Toxic 24: 123-44 (1993) (3) Yess NJ et al; J AOAC International 74: 273-80 (1991)]**PEER REVIEWED**

In a year-long study to evaluate exposure of tree nursery workers to various pesticides, exposure to triadimefon was confirmed via detections in hand rinses and patches attached to clothing(1); some exposure occurred in all four categories of worker types (applicators, weeders, scouts, packers)(1); in one tree nursery using triadimefon, positive patch detections occurred in 12 of 261 patches analyzed with a max and avg concn of 63.33 and 10.08 mg/patch, respectively(1). [(1) Lavy TL et al; Arch Environ Contam Toxicol 24: 123-44 (1993)]**PEER REVIEWED**

The rate of decay of triadimefon and its concentration after application was measured during cucumber cultivation in greenhouses under normal growing conditions(1). In preliminary experiments, the concentration of triadimefon in air was, at a sampling period of 0-2 hours after application, below the detection limit (3 ug/cu m). Hence, air exposure is likely of no concern with respect to human health. On the floor surfaces, the triadimefon concentrations were on average 0.010 ug/sq cm after low-volume spraying and 0.013 ug/sq cm after high-volume spraying. Six days after low-volume spraying, the concentration of triadimefon was below the detection limit (0.002 ug/sq cm), and after high-volume spraying, the concentration of triadimefon was estimated to be 0.004 ug/sq cm(1). [(1) Nilsson, U et al; J Agric Food Chem 44: 2878-2884 (1996)]**PEER REVIEWED**

Body Burden:

It has been reported that low levels of triadimefon metabolites have been detected in the urine of workers using triadimefon(1). [(1) Wang GM; Teratog Carcinog Mutagen 8: 117-26 (1988)]**PEER REVIEWED**

Emergency Medical Treatment:

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The following Overview, *** GENERAL OR UNKNOWN CHEMICAL ***, is relevant for this HSDB record chemical.Life Support:

o This overview assumes that basic life support measures have been instituted.Clinical Effects:

0.2.1 SUMMARY OF EXPOSURE 0.2.1.1 ACUTE EXPOSURE A) A SPECIFIC REVIEW on the clinical effects and treatment of individuals exposed to this agent HAS NOT YET BEEN PREPARED. The following pertains to the GENERAL EVALUATION and TREATMENT of individuals exposed to potentially toxic chemicals. B) GENERAL EVALUATION - 1) Exposed individuals should have a careful, thorough medical history and physical examination performed, looking for any abnormalities. Exposure to chemicals with a strong odor often results in such nonspecific symptoms as headache, dizziness, weakness, and nausea. C) IRRITATION - 1) Many chemicals cause irritation of the eyes, skin, and respiratory tract. In severe cases respiratory tract irritation can progress to ARDS/acute lung injury, which may be delayed in onset for up to 24 to 72 hours in some cases. 2) Irritation or burns of the esophagus or gastrointestinal tract are also possible if caustic or irritant chemicals are ingested. D) HYPERSENSITIVITY - 1) A number of chemical agents produce an allergic hypersensitivity dermatitis or asthma with bronchospasm and wheezing with chronic exposure.Laboratory:

A) A number of chemicals produce abnormalities of the hematopoietic system, liver, and kidneys. Monitoring complete blood count, urinalysis, and liver and kidney function tests is suggested for patients with significant exposure. B) If respiratory tract irritation or respiratory depression is evident, monitor arterial blood gases, chest x-ray,

and pulmonary function tests.Treatment Overview:

0.4.2 ORAL EXPOSURE A) GASTRIC LAVAGE 1) Significant esophageal or gastrointestinal tract irritation or burns may occur following ingestion. The possible benefit of early removal of some ingested material by cautious gastric lavage must be weighed against potential complications of bleeding or perforation. 2) GASTRIC LAVAGE: Consider after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion (generally within 1 hour). Protect airway by placement in Trendelenburg and left lateral decubitus position or by endotracheal intubation. Control any seizures first. a) CONTRAINDICATIONS: Loss of airway protective reflexes or decreased level of consciousness in unintubated patients; following ingestion of corrosives; hydrocarbons (high aspiration potential); patients at risk of hemorrhage or gastrointestinal perforation; and trivial or non-toxic ingestion. B) ACTIVATED CHARCOAL 1) Activated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. In general, metals and acids are poorly bound and patients ingesting these materials will not likely benefit from activated charcoal administration. a) Activated charcoal should not be given to patients ingesting strong acidic or basic caustic chemicals. Activated charcoal is also of unproven value in patients ingesting irritant chemicals, where it may obscure endoscopic findings when the procedure is justified. 2) ACTIVATED CHARCOAL: Administer charcoal as 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) DILUTION - 1) Immediate dilution with milk or water may be of benefit in caustic or irritant chemical ingestions. 2) DILUTION: Immediately dilute with 4 to 8 ounces (120 to 240 mL) of water or milk (not to exceed 4 ounces/120 mL in a child).

D) IRRITATION - 1) Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury. E) OBSERVATION CRITERIA - 1) Carefully observe patients with ingestion exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary. 2) Patients symptomatic following exposure should be observed in a controlled setting until all signs and symptoms have fully resolved. 0.4.3 INHALATION EXPOSURE A) DECONTAMINATION - 1) INHALATION: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. B) IRRITATION - 1) Respiratory tract irritation, if severe, can progress to pulmonary edema which may be delayed in onset up to 24 to 72 hours after exposure in some cases. C) ACUTE LUNG INJURY - 1) ACUTE LUNG INJURY: Maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Early use of PEEP and mechanical ventilation may be needed. D) BRONCHOSPASM - 1) If bronchospasm and wheezing occur, consider treatment with inhaled sympathomimetic agents. E) OBSERVATION CRITERIA - 1) Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary. 2) Patients symptomatic following exposure should be observed in a controlled setting until all signs and symptoms have fully resolved. 0.4.4 EYE EXPOSURE A) DECONTAMINATION: Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a

health care facility. 0.4.5 DERMAL EXPOSURE A) OVERVIEW 1) DERMAL DECONTAMINATION - a) 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. 2) PESTICIDES - a) DECONTAMINATION: Remove contaminated clothing and jewelry. Wash the skin, including hair and nails, vigorously; do repeated soap washings. Discard contaminated clothing. 3) IRRITATION - a) Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. 4) DERMAL ABSORPTION - a) Some chemicals can produce systemic poisoning by absorption through intact skin. Carefully observe patients with dermal exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.Range of Toxicity:

A) No specific range of toxicity can be established for the broad field of chemicals in general.[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**

Animal Toxicity Studies:

Non-Human Toxicity Excerpts:

Ornamentals may be damaged if used at excessive rates. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1000]**PEER REVIEWED**

Triadimefon is a fungicide that has recently been shown to incr motor activity & rates of schedule-controlled responding. These findings indicate that triadimefon resembles psychomotor stimulants & in this respect is a unique pesticide. The present experiment

was designed to evaluate triadimefon's effects on performance maintained by a multiple schedule of reinforcement & to compare triadimefon to known psychomotor stimulants. Four rats were trained to perform under a multi- FI 1-min & FI 5-min schedule of milk reinforcement. They then received a series of dosages of triadimefon (10-170 mg/kg, ip) & of methylphenidate (1-17.3 mg/kg, ip) in a counterbalanced order. Triadimefon increased response rates in both the FI 1-min & FI 5-min components. Methylphenidate did not consistently alter response rates in either component. Temporal patterns of responding were disrupted much more in the FI 5-min component than in the FI 1-min component by both triadimefon & methylphenidate. Performances were then evaluated following a series of dosages of d-amphetamine (0.3-3.0 mg/kg, ip) & chlorpromazine (0.5-2.0 mg/kg, ip). Response rates were increased by d-amphetamine in the FI 1-min component but not in the FI 5-min component. Like triadimefon & methylphenidate, d-amphetamine produced a greater disruption of response patterning in FI 5-min than in FI 1-min. Only chlorpromazine decreased response rates in both components. Chlorpromazine also disrupted FI 5-min response patterning, but left FI 1-min patterning intact. Although triadimefon did not closely resemble any of the comparison drugs, it had opposite effects on response rates from chlorpromazine in both components of the schedule & resembled d-amphetamine in its effects on FI 1-min response rates. The rate-increasing effects frequently obtained with psychomotor stimulants were more evident for triadimefon than for either methylphenidate or d-amphetamine. [Allen AR, Macphail RC; Pharmacol Biochem Behav 40 (4): 775-80 (1991)]**PEER REVIEWED**

Eight pesticides were tested in a medium-term bioassay based upon the induction of preneoplastic lesions in the liver. Rats were initially given diethylnitrosamine ip at a dose of 200 mg/kg body weight and 2 weeks later were treated with the pesticides for 6 weeks and then killed; all rats had a partial hepatectomy at week 3. Hepatocarcinogenic potential was assessed by comparing the number and area of glutathione S-transferase placental form positive foci in the liver with those of controls given diethylnitrosamine alone. Positive results were seen with p,p-DDT and triadimefon. Permethrin (mixture of 39% cis form and 61% trans form) showed borderline results. Permethrin (25/75), deltamethrin, cypermethrin (52/48), while trimorphamide and propineb gave negative results. These findings provide experimental evidence to indicate that compounds active in this assay have a potential for liver carcinogenicity in rodents. [Hakoi K et al; Teratogenesis Carcinog Mutagen 12 (6): 269-76 (1992)]**PEER REVIEWED**

Triadimefon, a triazole fungicide, has been observed to increase locomotion and induce stereotyped behavior in rodents. The present experiments designed to characterize the stereotyped behavior induced by triadimefon used a computer-supported observational method, and tested the hypothesis that these observed effects involved central dopaminergic systems. Adult male and female Sprague Dawley rats were injected with triadimefon (0, 50, 100, and 200 mg/kg) in corn oil (2 ml/kg ip) 4 hr prior to behavioral assessment. The two lowest doses of triadimefon increase the frequency of locomotion and rearing, while the highest dose induced highly stereotyped behaviors, including backward locomotion, circling, and head weaving. Immediately after behavioral testing,

the rats were sacrificed, and the striata and olfactory tubercles, terminal fields of the nigrostriatal and mesolimbic dopamine systems, respectively, were removed. Steady-state concentrations of the monoamines dopamine and serotonin and their metabolites were determined by HPLC-EC. In independent experiments, the direct effects of triadimefon on dopamine (D1 and D2) receptor binding and dopamine sensitive adenylate cyclase activity were assessed in vitro using rat striata. Dopamine concentrations were increased in olfactory tubercles, but decreased in striatum. Concentrations of 5-hydroxyindoleacetic acid (the major metabolite of serotonin) were increased only in striatum, and only in animals treated with 200 mg/kg triadimefon. In vitro, triadimefon neither competed with D1 or D2 dopaminergic radioligands nor affected dopamine stimulated adenylate cyclase activity. Together these behavioral and biochemical data lend support to the hypothesis that triadimefon may have actions similar to those produced by indirect-acting dopamine agonists. [Walker QD et al; Toxicol Appl Pharmacol 102 (3): 474-85 (1990)]**PEER REVIEWED**

Ergosterol biosynthesis inhibitor. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1000]**PEER REVIEWED**

Non-Human Toxicity Values:

LD50 Rat oral 90 mg/kg [Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-336]**PEER REVIEWED**

LD50 Rat dermal 310 mg/kg [Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-336]**PEER REVIEWED**

LC50 Rat inhalation 3.27 mg/l air/4 hr (dust) [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LD50 Rat dermal >5000 mg/kg [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LD50 Mouse oral approx 1000 mg/kg [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LD50 Rabbit oral 250-500 mg/kg [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LD50 Dog oral >500 mg/kg [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

Ecotoxicity Values:

LD50 Canary oral >1000 mg/kg [Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A401/Aug 87]**PEER REVIEWED**

LD50 Japanese quail oral 1750-2500 mg/kg [Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A401/Aug 87]**PEER REVIEWED**

LC50 Mallard duck oral >10,000 mg/kg diet/8 day [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LC50 Bobwhite quail oral >4640 mg/kg diet/8 day [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LC50 Bluegill sunfish 11 mg/l/96 hr /Conditions of bioassay not specified/ [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

LC50 Carassius auratus (Goldfish) 10-50 mg/l/96 hr /Conditions of bioassay not specified/ [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. 813]**PEER REVIEWED**

Metabolism/Pharmacokinetics:

Metabolism/Metabolites:

Triadimefon was applied to cucumber, tomato, bean and wheat plants. Differences were primarily quantitative. Triadimenol, the 2-butenol analog, was formed in each case.

[Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980. 524]**PEER REVIEWED**

In plants, the carbonyl group is reduced to a hydroxyl group, with the formation of triadimenol. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

... Metabolism occurs in the liver, mostly to triadimenol & its glucuronic acid conjugates. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

Absorption, Distribution & Excretion:

Absorbed by the roots & leaves, with ready translocation in young growing tissues, but less ready translocation in older, woody tissues. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1000]**PEER REVIEWED**

In mammals, following oral admin, 83-96% is excreted unchanged in the urine & feces within 2 to 3 days. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

The percutaneous absorption of (14)C phenoxy ring labeled triadimefon was studied in adult & young male & female Sprague Dawley rats. Triadimefon was applied (41.1 to 46.4 ug/sq cm) in 0.2 ml of acetone to areas comprising 3% of the body surface (7.0 to 14.5 sq cm). Thirty six animals were treated at the initiation of each study.Groups of 3 animals were subsequently killed at 1, 4, 8, 12, 24, 48, 72, 96, 120, 144, 168, & 192 hr after treatment. Skin from the treated area as well as blood, heart, liver, kidneys, remaining carcass, urine, & feces were analyzed for (14)C by scintillation counting techniques. Based on 14 counts, triadimefon was lost more rapidly from the skin of young animals (half-life, 20 to 25 hr) than from the skin of adult animals (half-life, 29 to 53 hr). Recovery studies indicated that adult males, adult females, young males, & young females, respectively, absorbed 53, 82, 57, & 52% of the dose. The rest of the dose based on material balance was presumably lost by evaporation. Approx 2.5 to 3.9% of the dose penetrated the skin in 1 hr & was available for absorption. The rate of entry triadimefon into blood was 2 to 2.5 times faster for young than that observed in adult animals. Elimination of it from blood was faster in the case of the young animals. Triadimefon was absorbed through the skins of the adult male, adult female, young male, & young female rat, respectively, at rates of 0.20, 0.50, 0.58, & 0.48 ug/hr/sq cm of skin. [Knaak JB et al, Toxicol Appl Pharmacol 72 (3): 406-16 (1984)]**PEER REVIEWED**

Triadimefon is absorbed across the skin.

[U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: http://www.epa.gov/pesticides/safety/healthcare 154]**PEER REVIEWED**

Biological Half-Life:

Half-life in blood plasma is approx 2.5 hr. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1001]**PEER REVIEWED**

Mechanism of Action:

In order to elucidate the action mechanism of prochloraz and triadimefon, the mycelia of the Valsa ceratosperma were treated with the compounds in vitro. Analysis by GLC of the sterol extract from Valsa ceratosperma mycelia revealed one major peak and two minor peaks. Their relative retention time relative to chloresterol were 1.29, 1.48 and 1.82. The compounds with relative retention time 1.29 and relative retention time 1.82 and were identified as ergosterol and 2, 4-methylenedihydrolanosterol by GC/MS, respectively. Five ppm of mycelia caused decrease in ergosterol content, whereas increase in 2,4-methylenedihydroanoserol content in mycelia. The longer treatment time and the higher concentrations of the chemicals resulted in the greater decrease in ergosterol and the greater increase in 2,4-methylenedihydrolanosterol. Based on the analysis, it is considered that the two chemicals inhibit the ergosterol biosynthesis in Valsa ceratosperma by blocking C-14 demethylation as found previously in other fungi and yeasts. [Hong JU et al; J Korean Agric Chem Soc 32 (3): 270-7 (1989)]**PEER REVIEWED**

Pharmacology:

Environmental Fate & Exposure:

Environmental Fate/Exposure Summary:

Triadimefon's production and use as a fungicide is expected to result in its direct release to the environment. If released to air, a vapor pressure of 1.50X10-8 mm Hg at 25 deg C indicates triadimefon will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triadimefon will be removed from the atmosphere by wet and dry deposition. If released to soil, triadimefon is expected to have moderate to low mobility based upon a Koc ranging from 150-510. Volatilization from moist soil surfaces

is not expected to be an important fate process based upon a Henry's Law constant of 8.10X10-11 atm-cu m/mole. Triadimefon is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Soil degradation studies have indicated that triadimefon can degrade at extremely variable rates depending upon environmental factors. Laboratory persistence studies using a silty clay loam soil with no prior exposure to triadimefon reported a soil half-life of 15 days, while West German field tests using various soils and conditions found half-lives ranging from 10 days to 7 months. If released into water, triadimefon is not expected to adsorb to suspended solids and sediment based upon the Koc values. Volatilization from water is not expected to be an important fate process based upon this compound's Henry's Law constant. The photo stability of triadimefon in aqueous media when irradiated with UV light (> 290 nm) in the presence of humic and fulvic acids (isolated from soil) and in their absence was studied. The results showed that after four hours of irradiation, 87% was degraded whereas irradiation in the presence of humic and fulvic acids resulted in 91.7 and 93.6% degradation, respectively. An estimated BCF of 27 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis in water can occur, albeit slowly, via catalytic action by water salts, mainly divalent cations; degradation in water at 70 degrees C has been reported to reach 90% in eight weeks. Occupational exposure to triadimefon may occur through inhalation of dust and dermal contact with this compound at workplaces where triadimefon is produced or used. Monitoring data indicate that the general population may be exposed to triadimefon via ingestion of food, but it has been only rarely detected in food. (SRC) **PEER REVIEWED**

Probable Routes of Human Exposure:

Occupational exposure to triadimefon occurs through dermal contact and inhalation of sprays, especially to workers applying the compound as a pesticide(1). Dermal exposure to triadimefon is reported to occur in tree nursery workers who handle triadimefon pesticides(2). Since triadimefon has been detected occasionally in the U.S. foods (3), limited exposure to the general population may occur through consumption of foods containing triadimefon residues (SRC). [(1) Parmeggiani L; Encycl Occup Health and Safety 3rd ed. Geneva, Switzerland: International Labor Office pp. 1616-46 (1983) (2) Lavy TL et al; Arch Environ Contam Toxic 24: 123-44 (1993) (3) Yess NJ et al; J AOAC International 74: 273-80 (1991)]**PEER REVIEWED**

In a year-long study to evaluate exposure of tree nursery workers to various pesticides, exposure to triadimefon was confirmed via detections in hand rinses and patches attached to clothing(1); some exposure occurred in all four categories of worker types (applicators, weeders, scouts, packers)(1); in one tree nursery using triadimefon, positive patch detections occurred in 12 of 261 patches analyzed with a max and avg concn of 63.33 and 10.08 mg/patch, respectively(1). [(1) Lavy TL et al; Arch Environ Contam Toxicol 24: 123-44 (1993)]**PEER REVIEWED**

The rate of decay of triadimefon and its concentration after application was measured during cucumber cultivation in greenhouses under normal growing conditions(1). In preliminary experiments, the concentration of triadimefon in air was, at a sampling period of 0-2 hours after application, below the detection limit (3 ug/cu m). Hence, air exposure is likely of no concern with respect to human health. On the floor surfaces, the triadimefon concentrations were on average 0.010 ug/sq cm after low-volume spraying and 0.013 ug/sq cm after high-volume spraying. Six days after low-volume spraying, the concentration of triadimefon was below the detection limit (0.002 ug/sq cm), and after high-volume spraying, the concentration of triadimefon was estimated to be 0.004 ug/sq cm(1). [(1) Nilsson, U et al; J Agric Food Chem 44: 2878-2884 (1996)]**PEER REVIEWED**

Body Burden:

It has been reported that low levels of triadimefon metabolites have been detected in the urine of workers using triadimefon(1). [(1) Wang GM; Teratog Carcinog Mutagen 8: 117-26 (1988)]**PEER REVIEWED**

Artificial Pollution Sources:

Triadimefon's production and use as a fungicide(1,2) is expected to result in its direct release to the environment(SRC). [(1) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed. Surrey, England: British Crop Protection Council p. 1217 (1997) (2) Farm Chemicals Handbook 2001. Willoughby, Ohio: Meister p. C 398 (2001)]**PEER REVIEWED**

Environmental Fate:

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value ranging from 150-510(2,3), indicates that triadimefon is expected to have moderate to low mobility in soil(SRC). On September 15 and again on October 27 of 1992, triadimefon was applied to 8 field plots(sand at pH 6.7) at a rate of 11.32 g active ingredient/plot as a dispersible powder in water(9). Analysis of leachate sampled 37 cm below the soil surface found that the concentration of triadimefon was 7, 4, 9, 16, and 4 ppb on October 30, November 7, 12, 24, and December 18, respectively. Although leachate samples were collected and analyzed until June 8 1993, triadimefon was not detected after December 18(9). Volatilization of triadimefon from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.10X10-11 atm-cu m/mole(4). Triadimefon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.50X10-8 mm Hg(5). Soil degradation studies have indicated that triadimefon can degrade at extremely variable rates depending upon environmental factors. Laboratory persistence studies using a silty clay loam soil with no prior exposure

to triadimefon found a soil half-life of 15 days(6), while West German field tests using various soils and conditions found half-lives ranging from 10 days to 7 months(7). Photolysis on soil surfaces may also be an important fate process. Triadimefon was applied to alluvial and laterite soil, irradiated with natural sunlight and monitored for degradation(8). Under these conditions, triadimefon had a half-life of 16.09 and 18.24 days on alluvial and laterite soil, respectively(8). [(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Patil SG et al; Pest Sci 22: 333-42 (1988) (3) Suzuki T et al; Environ Sci Tech 32: 920-929 (1998) (4) USDA; Agric Res Service. ARS Pesticide Properties Database on Triadimefon (43121-43-3). Available at http://wizard.arsusda.gov/acsl/textfiles/TRIADIMEFON as of June 1, 2001. (5) Wauchope RD et al; Rev Environ Contam Tox 123: 1-35 (1991) (6) Patil SG et al; Pest Sci 22: 333-42 (1988) (7) Cabras P et al; Review Environment Contamination Toxicology 99: 82-117 (1987) (8) Nag SK, Dureja P; Pest Sci 48: 247-252 (1996) (9) Peprovic AM et al; Chemosphere 29: 415-419 (1994)]**PEER REVIEWED**

AQUATIC FATE: Based on a classification scheme(1), a Koc value ranging from 150-510(2,3), indicates that triadimefon is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 8.10X10-11 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 27(SRC), from a log Kow of 2.77(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC).The photo stability of triadimefon in aqueous media when irradiated with UV light (> 290 nm) in the presence of humic and fulvic acids (isolated from soil) and in their absence was studied(9). The results showed that after four hours of irradiation, 87% was degraded whereas irradiation in the presence of humic and fulvic acids resulted in 91.7 and 93.6% degradation, respectively. In control experiments (not radiated with and without humic/fulvic acids), there was no degradation(9). [(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Patil SG et al; Pest Sci 22: 333-42 (1988) (3) Suzuki T et al; Environ Sci Tech 32: 920-929 (1998) (4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990) (5) USDA; Agric Res Service. ARS Pesticide Properties Database on Triadimefon (43121-43-3). Available at http://wizard.arsusda.gov/acsl/textfiles/TRIADIMEFON as of June 1, 2001. (6) Franke C et al; Chemosphere 29: 1501-14 (1994) (7) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 122 (1995) (8) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999) (9) Moza PN et al; Chemosphere 30: 605-610 (1995)]**PEER REVIEWED**

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triadimefon, which has a vapor pressure of 1.50X10-8 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triadimefon may be removed from the air by wet and dry deposition(SRC). Triadimefon absorbs light in the environmental spectrum. When triadimefon in aqueous media was irradiated with UV light (> 290 nm), 87% was degraded after four hours(3).

[(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) Wauchope RD et al; Rev Environ Contam Tox 123: 1-35 (1991) (3) Moza PN et al; Chemosphere 30: 605-610 (1995)]**PEER REVIEWED**

Environmental Biodegradation:

AEROBIC: To study the fate of pesticides in golf compost heaps, researchers applied triadimefon to soil at 1.4 ug/g and to thatch and grass clippings at 2.7 ug/g and monitored for degradation(1). They found that triadimefon had a half-life in soil, thatch, and grass of 3.9, 7.9, and 1.8 days, respectively. The U.S. Department of Agriculture's Pesticide Properties Database lists a soil half-life of 26 days for triadimefon(2). Laboratory persistence studies using a silty clay loam soil with no prior exposure to triadimefon found a soil half-life of 15 days(3). West German field tests in various soils and conditions found half-lives ranging from 10 days to 7 months(4). Various fungi have been found to metabolize triadimefon to triadimenol(5). [(1) Frederick EK et al; Bull Environ Contam Toxicol 53: 536-542 (1994) (2) Wauchope RD et al; Rev Environ Contam Tox 123: 1-35 (1991) (3) Patil SG et al; Pest Sci 22: 333-42 (1988) (4) Cabras P et al; Rev Environ Contam Tox 99: 82-117 (1987) (5) Deas AHB et al; Pest Sci 15: 63-70 (1984)]**PEER REVIEWED**

Environmental Abiotic Degradation:

Based upon a vapor pressure of 1.50X10-8 mm Hg (1), triadimefon is expected to exist in the particulate phase in the atmosphere and therefore is not expected to react with atmospheric hydroxyl radicals. Hydrolysis in water can occur, albeit slowly, via catalytic action by water salts, mainly divalent cations(2); degradation in water at 70 degrees C has been reported to reach 90% in eight weeks. The photostability of triadimefon in aqueous media when irradiated with UV light (> 290 nm) in the presence of humic and fulvic acids (isolated from soil) and in their absence was studied(3). The results showed that after four hours of irradiation, 87% degraded whereas irradiation in the presence of humic and fulvic acids resulted in 91.7 and 93.6% degradation, respectively. Photodegradation products included 4-chlorophenol, 4-chloro-1,3-benzenediol, 2,4-dihydroxybenzaldehyde, and phenoxy, 3-3 dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone. In control experiments (not radiated with and without humic/fulvic acids), there was no degradation(3). Triadimefon was applied to glass petri dishes and soil(alluvial and laterite), irradiated with both natural sunlight and UV lamp (> 290 nm), and monitored for degradation(4). The study found that while using the UV lamp, triadimefon had a half-life of 9.46, 21.8, and 1.32 hours on alluvial, laterite, and glass, respectively. Using natural sunlight, triadimefon had a half-life of 16.09, 18.24, and 0.12 days on alluvial, laterite, and glass, respectively(4). [(1) Wauchope RD et al; Rev Environ Contam Tox 123: 1-35 (1991) (2) Cabras P et al; Rev Environ Contam Tox 99: 82-117 (1987) (3) Moza PN et al; Chemosphere 30: 605-610 (1995) (4) Nag SK, Dureja P; Pest Sci 48: 247-252 (1996)]**PEER REVIEWED**

Environmental Bioconcentration:

An estimated BCF of 27 was calculated for triadimefon(SRC), using a log Kow of 2.77(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(SRC). [(1) Hansch C et al; Exploring QSAR.Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 122 (1995) (2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999) (3) Franke C et al; Chemosphere 29: 1501-14 (1994)]**PEER REVIEWED**

Soil Adsorption/Mobility:

Triadimefon had a Koc value of 150 in turfgrass soil and 300 in loam soil(1). In another study, a measured soil Kd (partition coefficient) of 8.33 in a silty clay loam soil of 2.8% organic matter(2) can be used to determine a Koc value of 510(SRC). According to a classification scheme(3), these Koc values suggest that triadimefon is expected to have moderate to low mobility depending upon the soil. [(1) Suzuki T et al; Environ Sci Tech 32: 920-929 (1998) (2) Patil SG et al; Pest Sci 22: 333-42 (1988) (3) Swann RL et al; Res Rev 85: 17-28 (1983)]**PEER REVIEWED**

Volatilization from Water/Soil:

The Henry's Law constant for triadimefon is 8.10X10-11 atm-cu m/mole(1). This Henry's Law constant indicates that triadimefon is expected to be essentially nonvolatile from water surfaces(2). Triadimefon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure 1.50X10-8 mm Hg(3). [(1) USDA; Agric Res Service. ARS Pesticide Properties Database on Triadimefon (43121-43-3). Available at http://wizard.arsusda.gov/acsl/textfiles/TRIADIMEFON as of June 1, 2001. (2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (3) Wauchope RD et al; Rev Environ Contam Tox 123: 1-35 (1991)]**PEER REVIEWED**

Environmental Water Concentrations:

GROUNDWATER: From July 1994 through June 1995 the Department of Pesticide Regulation (Cal/EPA) compiled well water sample data from various counties throughout California(1). Out of seven wells sampled, triadimefon was detected in 4 groundwater samples collected from Merced County, in 1 groundwater sample from Santa Barbara County, and in 1 groundwater sample from Ventura County(concentration not reported). EPA tested water samples from 783 rural domestic wells and 566 community water system wells, nationwide, for the presence of 101 water pesticides(time period not indicated)(2). Triadimefon was not detected in any of the wells sampled at a detection

limit of 0.16 ug/l. In 1984, water samples were collected from 206 water work wells in Germany and analyzed for 35 different pesticides(3); triadimefon was not detected above a detection limit of 0.05 ug/l(3). [(1) California EPA; Sampling for Pesticide Residues in California Well Water. in California Environmental Protection Agency, Department Pesticide Regulation, 10th Annual Report (1995) (2) USEPA; National Pesticide Survey: Survey Analytes. US EPA Off of Pest and Tox Sub NTIS PB 93-116 010 (1990) (3) Iwan VJ; Gesunde Pflanz 40: 208-13 (1988)]**PEER REVIEWED**

SURFACE WATER: In 1989, water samples were collected from the Rhine River at several locations in the Netherlands Delta(1). Samples were taken near the German border at Lobith (17/03/89 and 15/09/89), downstream of Rotterdam Harbor at Maassluis (26/05/89 and 22/09/89), along the mainstream at Werkendam (29/09/89), in a semi-stagnant branch of Haringvliet (19/05/89) and in the out lead of the Ijssel at Kampen (21/04/89). Triadimefon was detected only at Lobith on 15/09/89 at 0.019 ug/l(1). [(1) Hendricks AJ et al; Wat Res 28: 581-598 (1994)]**PEER REVIEWED**

Food Survey Values:

Triadimefon is one of many pesticides that has been detected in U.S. foods by the US Food and Drug Admin's regulatory monitoring of domestic foods for fiscal years 1983-1986(1); frequencies of occurrence and concns were not reported(1). In a US monitoring survey of 6970 produce samples (fruits and vegetables) collected between 1989 and 1991, triadimefon was detected (detection limit of 0.75 ppm) in only one sample(2); the concn in the sample (from a pear) was not reported, but it was said to be above the tolerable limit set by the EPA(2). During a 5 yr study conducted during 1981-1986, the Los Angeles District Office of the FDA analyzed 19,851 samples of domestic and imported food for pesticide residues(3,4); triadimefon was detected in 9 samples at concns ranging from 0.05 to 0.5 ppm(3,4). In 1989 monitoring conducted by the California Dept of Food and Agric, triadimefon was not detected (detection limit of 0.3 ppm) in 1 cantaloupe, 18 grape, or 13 sugar beet samples(5). [(1) Yess NJ et al; J AOAC International 74: 273-80 (1991) (2) Schattenberg HJ III, Hsu JP; J AOAC Internatl 75: 925-33 (1992) (3) Luke MA et al; J Assoc Off Anal Chem 71: 415-20 (1988) (4) Hundley HK et al; J Assoc Off Anal Chem 71: 875-92 (1988) (5) Okumura D et al; Rev Environ Contam Toxicol 118: 87-151 (1991)]**PEER REVIEWED**

In 1994, 11,348 food samples were analyzed for pesticide residues; 5474 were domestic and 5874 were imported food items(1). Triadimefon was not detected in any of the samples (detection limit not indicated). Strawberries were bought from the supermarkets in Nara, Japan from January to March 1992 and again in 1993 and analyzed for pesticide concentrations(2). The concentration of triadimefon in strawberries collected in 1992 ranged from 0.02-0.04 ug/g and in 1993 ranged from 0.01-0.04 ug/g. From January 1995 to December 1996, 4182 food samples were collected in Denmark and analyzed by the

Danish National Pesticide Monitoring Program(3). Triadimefon was not detected in any of the samples (detection limit not indicated). [(1) FDA; Food and Drug Administration Pesticide Program. Residue Monitoring-1994. J AOAC Int 78 (1995) (2) Nagami H; Bull Environ Contam Toxicol 58:53-60 (1997) (3) Juhler RK et al; J AOAC Internat 82: 337-358 (1999)]**PEER REVIEWED**

Plant Concentrations:

The rate of decay of triadimefon and its concentration after application was measured during cucumber cultivation in greenhouses under normal growing conditions(1). One day after high-volume spraying, the residue concentration on leaves was on average 0.009 ug/sq cm. One week after spraying, no changes in concentration on the surfaces were observed(1). [(1) Nilsson, U et al; J Agric Food Chem 44: 2878-2884 (1996)]**PEER REVIEWED**

Fish/Seafood Concentrations:

Concentrations of various organic micro contaminants were measured in zebra mussels and eel from the Rhine-Meuse Basin from 1993 to 1994(1). Triadimefon was not detected in either zebra mussels or eel at a detection limit of 5.0 ug/kg wet weight. [(1) Hendricks AJ et al; Environ Tox Chem 17: 1885-1898 (1998)]**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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 1-(4-Chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone is found on List B. Case No: 2700; Pesticide type: fungicide; 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): 1-(4-Chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-

triazol-1-yl)-2-butanone; Data Call-in (DCI) Date(s): 04/29/91, 03/03/95, 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.214 (Spring, 1998) EPA 738-R-98-002]**PEER REVIEWED**

Tolerances are established for the combined residues of the fungicide 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol- 1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in or on the following raw agricultural commodities: apple pomace (wet and dry); apples; barley, milled fractions (except flour); cattle, fat; cattle, meat; cattle, mbyp; chick pea, seed (dry); cucurbits; eggs; grapes; goats, fat; goats, meat; goats, mbyp; grape pomace (wet and dry); grass (forage); grass (seed cleanings including hulls); grass, seed straw (including chaff); hogs, fat; hogs, meat; hogs, mbyp; horses, fat; horses, meat; horses, mbyp; milk; nectarines; pears; pineapples (fresh); poultry, fat; poultry, meat; poultry, mbyp; raisin waste; sheep, fat; sheep, meat; sheep, mbyp; sugar beets; sugar beets (tops); wheat, grain; wheat, green forage; wheat, milled fractions (except flour); wheat, straw. [40 CFR 180.410(a) (7/1/2000)]**PEER REVIEWED**

Time-limited tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in connection with use of the pesticide under the section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table: artichokes, expiration/revocation date: 9/1/99; asparagus, expiration/revocation date: 9/1/99; chili peppers, expiration/revocation date: 11/8/97. [40 CFR 180.410(b) (7/1/2000)]**PEER REVIEWED**

Tolerances with regional registration are established for the combined residues of the fungicide 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in or on the following raw agricultural commodities: raspberries. [40 CFR 180.410(c) (7/1/2000)]**PEER REVIEWED**

Acceptable Daily Intakes:

FAO/WHO ADI: 0.03 mg/kg [FAO/WHO; Pesticide Residues in Food - 1992. Evaluations Part 1 - Residues p.878 Plant Prod Protection Paper 118 (1992)]**PEER REVIEWED**

Allowable Tolerances:

Tolerances are established for the combined residues of the fungicide 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol- 1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in or on the following raw agricultural commodities: apple pomace (wet and dry), 4.0 ppm; apples, 1.0 ppm; barley, milled fractions (except flour), 4.0 ppm; cattle, fat, 1.0 ppm; cattle, meat, 1.0 ppm; cattle, mbyp, 1.0 ppm; chick pea, seed (dry), 0.1 ppm; cucurbits, 0.3 ppm; eggs, 0.04 ppm; grapes, 1.0 ppm; goats, fat, 1.0 ppm; goats, meat, 1.0 ppm; goats, mbyp, 1.0 ppm; grape pomace (wet and dry), 3.0 ppm; grass (forage), 0.2 ppm; grass (seed cleanings including hulls), 145.0 ppm; grass, seed straw (including chaff), 105.0 ppm; hogs, fat, 0.04 ppm, hogs, meat, 0.04 ppm; hogs, mbyp, 0.04 ppm; horses, fat, 1.0 ppm; horses, meat, 1.0 ppm; horses, mbyp, 1.0 ppm; milk, 0.04 ppm; nectarines, 4.0 ppm; pears, 1.0 ppm; pineapples (fresh), 3.0 ppm; poultry, fat, 0.04 ppm; poultry, meat, 0.04 ppm; poultry, mbyp, 0.04 ppm; raisin waste, 7.0 ppm; sheep, fat, 1.0 ppm; sheep, meat, 1.0 ppm; sheep, mbyp, 1.0 ppm; sugar beets, 0.5 ppm; sugar beets (tops), 3.0 ppm; wheat, grain, 1.0 ppm; wheat, green forage, 15.0 ppm; wheat, milled fractions (except flour), 4.0 ppm; wheat, straw, 5.0 ppm. [40 CFR 180.410(a) (7/1/2000)]**PEER REVIEWED**

Time-limited tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in connection with use of the pesticide under the section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specified in the following table: artichokes, 0.6 ppm, expiration/revocation date: 9/1/99; asparagus, 0.15 ppm, expiration/revocation date: 9/1/99; chili peppers, 0.5 ppm, expiration/revocation date: 11/8/97. [40 CFR 180.410(b) (7/1/2000)]**PEER REVIEWED**

Tolerances with regional registration are established for the combined residues of the fungicide 1-(4-chlorophenoxy)-3,3-dimethyl-1(1H-1,2,4-triazol-1-yl)-2-butanone and its metabolites containing chlorophenoxy and triazole moieties (expressed as the fungicide) in or on the following raw agricultural commodities: raspberries, 2.0 ppm. [40 CFR 180.410(c) (7/1/2000)]**PEER REVIEWED**

Chemical/Physical Properties:

Molecular Formula:

C14-H16-Cl-N3-O2 [Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989. 1510]**PEER REVIEWED**

Molecular Weight:

293.75 [Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996. 1636]**PEER REVIEWED**

Color/Form:

Colorless solid [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Odor:

Characteristic odor [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Melting Point:

82 deg C [Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996. 1636]**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. A401/AUG 87]**PEER REVIEWED**

Density/Specific Gravity:

1.283 @ 21.5 deg C [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Octanol/Water Partition Coefficient:

log Kow= 2.77 [Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995. 122]**PEER REVIEWED**

Solubilities:

Solubility in water at 20 deg C: 260 mg/l. Moderately sol in most organic solvents except aliphatics. [Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996. 1636]**PEER REVIEWED**

Solubility (20 deg C): 0.6-1.2 kg/kg cyclohexanone [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. 813]**PEER REVIEWED**

In dichloromethane , toluene >200, isopropanol 99, hexane 6.3 (all in g/l, 20 deg C) [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Water solubility of 71.5 mg/l at 25 deg C. [Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991)]**PEER REVIEWED**

Spectral Properties:

Intense mass spectral peaks: 57 m/z (100%), 208 m/z (44%), 85 m/z (25%), 210 m/z (15%) [Hites, R.A. Handbook of Mass Spectra of Environmental Contaminants. Boca Raton, FL: CRC Press Inc., 1985. 360]**PEER REVIEWED**

Vapor Pressure:

1.5X10-8 mm Hg @ 25 deg C [Wauchope RD et al; Rev Environ Contam Toxicol 123: 1-35 (1991)]**PEER REVIEWED**

Other Chemical/Physical Properties:

Henry's Law constant = 8.10X10-11 atm-cu m/mole @ 25 deg C

[USDA; Agric Res Service. ARS Pesticide Properties Database on Triadimefon (43121-43-3). Available at http://wizard.arsusda.gov/acsl/textfiles/TRIADIMEFON as of June 1, 2001.]**PEER REVIEWED**

Chemical Safety & Handling:

Skin, Eye and Respiratory Irritations:

It causes irritation if eyes are contaminated. [U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: http://www.epa.gov/pesticides/safety/healthcare 154]**PEER REVIEWED**

Flash Point:

162 deg F /100 deg C/ [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

Fire Fighting Procedures:

Water spray, foam, carbon dioxide. [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

Toxic Combustion Products:

When heated to decomposition it emits very toxic fumes of /chlorides & nitrogen oxides/. [Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996. 805]**PEER REVIEWED**

Hazardous Decomposition:

When heated to decomposition it emits very toxic fumes of /hydrogen chloride & nitrogen oxides/. [Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996. 805]**PEER REVIEWED**

Protective Equipment & Clothing:

Wear hat, long sleeved shirt, long legged trousers or overalls during mixing, loading and application. Wear rubber or neoprene gloves and dust mask during mixing and loading. [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

Preventive Measures:

Do not enter treated areas without protective clothing until spray has dried. [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

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. **PEER REVIEWED**

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning. **PEER REVIEWED**

Stability/Shelf Life:

Stable to hydrolysis at 22 deg C. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994. 1000]**PEER REVIEWED**

It is stable at 20 deg C for 7 days at pH1 and pH13. [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. 813]**PEER REVIEWED**

Storage Conditions:

Store in a cool, dry place and prevent cross contamination with other pesticides, fertilizers, food or feed. Store in original container. Keep out of reach of children, preferably in a locked area. [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

Cleanup Methods:

If material is spilled or container leaking, carefully sweep material into a pile. Do not walk through spilled material and keep unauthorized people away. [Farm Chemicals Handbook 1993. Willoughby, OH: Meister Publishing Co., 1993.,p. C-41]**PEER REVIEWED**

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. **PEER REVIEWED**

Occupational Exposure Standards:

Manufacturing/Use Information:

Major Uses:

For Triadimefon (USEPA/OPP Pesticide Code: 109901) 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./ [U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Triadimefon (43121-43-3). Available from the Database Query page at http://www.cdpr.ca.gov/docs/epa/epamenu.htm as of May 24, 2001.]**PEER REVIEWED**

Active against mildews and rusts of grains, fruits, vegetables and ornamentals.

[Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996. 1636]**PEER REVIEWED**

Experimental systemic fungicide used for control of wheat leaf rust. [Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984.,p. II-336]**PEER REVIEWED**

Fungicide [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Triadimefon with carbendazim and sodium alginate is used to protect pruning wounds on apple and pear trees. [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. 813]**PEER REVIEWED**

Manufacturers:

Bayer Corporation, 100 Bayer Rd., Pittsburgh, PA 15205-9741, (412) 777-2000; Production sites: Baytown, TX 77520; Kansas City, MO 64120 [SRI International. 2000 Directory of Chemical Producers -- United States. SRI Consulting, Menlo Park: CA 2000 793]**PEER REVIEWED**

General Manufacturing Information:

Compatible with wettable powder formulations of other pesticides. [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Formulations/Preparations:

USEPA/OPP Pesticide Code 109901; Trade Names: Bayleton; Amiral; Bay MEB 6447; MEB 6447. [U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Triademefon (43121-43-3). Available from the Database Query page at http://www.cdpr.ca.gov/docs/epa/epamenu.htm as of May 24, 2001.]**PEER REVIEWED**

Wettable powder; emulsifiable concentrate; paste; dustable powder; water dispersible granules

[Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Mixtures: Triadimefon + captan; carbendazim; propineb; cymoxanil; tebucanazole; sulfur [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Dry flowable, emulsifiable concentrate, granule, wettable powder [Farm Chemicals Handbook 2001. Willoughby, Ohio: Meister 2001.,p. C 398]**PEER REVIEWED**

Consumption Patterns:

The estimated amount of triadimefon applied in the United States in 1982 and 1989 was 52 and 250 (1000 lbs AI/year), respectively. [Gianessi LP; U.S. Pesticide Use Trends: 1966-1989. Resources for the Future, Washington D.C. (1992)]**PEER REVIEWED**

Laboratory Methods:

Clinical Laboratory Methods:

GC/MS determination of Bayleton and its metabolites in cattle tissues and milk; and in poultry tissues and eggs. Recoveries ranged from 68 to 104% for duplicate beef liver samples fortified at the 0.05 and 0.1 ppm levels. Recoveries ranged from 76 to 120% for duplicate eggs samples fortified at the 0.005 and 0.01 ppm levels. Detection limit for both beef liver and eggs was 0.01 ppm. [FDA Pesticide Analytical Manual Vol 2 (Oct): (1989)]**PEER REVIEWED**

Analytic Laboratory Methods:

Triadimefon in pesticide formulations is determined by liquid chromatography, using 4-chlorophenyl sulfoxide as internal standard. [Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC: Association of Analytical Chemists, 1990,p. V1 228]**PEER REVIEWED**

Product analysis is by HPLC or by IR spectrometry. Residues of triadimefon and the corresponding alcohol (triadimenol) may be determined by GLC.

[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. 814]**PEER REVIEWED**

Analysis of residues: (1) By enzyme-linked immunosorbent assay. (2) By capillary GC. [Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987.,p. A401/AUG 87]**PEER REVIEWED**

Special References:

Synonyms and Identifiers:

Synonyms:

Amiral **PEER REVIEWED**

Bay 6681 F **PEER REVIEWED**

Bayleton **PEER REVIEWED**

Bayleton BM **PEER REVIEWED**

Bayleton BM gel **PEER REVIEWED**

Bayleton CF **PEER REVIEWED**

Bayleton Total **PEER REVIEWED**

Bayleton triple **PEER REVIEWED**

Bay MEB 6447 **PEER REVIEWED**

1-((tert-BUTYLCARBONYL-4-CHLOROPHENOXY)METHYL)-1H-1,2,4-TRIAZOLE

**PEER REVIEWED**

1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butanone **PEER REVIEWED**

1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone **PEER REVIEWED**

Diametom B **PEER REVIEWED**

Pesticide Code: 109901 **PEER REVIEWED**

MEB 6447 **PEER REVIEWED**

Triadimefone **PEER REVIEWED**

Formulations/Preparations:

USEPA/OPP Pesticide Code 109901; Trade Names: Bayleton; Amiral; Bay MEB 6447; MEB 6447. [U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Triademefon (43121-43-3). Available from the Database Query page at http://www.cdpr.ca.gov/docs/epa/epamenu.htm as of May 24, 2001.]**PEER REVIEWED**

Wettable powder; emulsifiable concentrate; paste; dustable powder; water dispersible granules [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Mixtures: Triadimefon + captan; carbendazim; propineb; cymoxanil; tebucanazole; sulfur [Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997 1217]**PEER REVIEWED**

Dry flowable, emulsifiable concentrate, granule, wettable powder [Farm Chemicals Handbook 2001. Willoughby, Ohio: Meister 2001.,p. C 398]**PEER REVIEWED**

Administrative Information:

Hazardous Substances Databank Number: 6857

Last Revision Date: 20030214

Last Review Date: Reviewed by SRP on 9/15/2001

Update History:

Complete Update on 02/14/2003, 1 field added/edited/deleted.Complete Update on 11/08/2002, 1 field added/edited/deleted.Complete Update on 08/06/2002, 1 field added/edited/deleted.Complete Update on 04/19/2002, 46 fields added/edited/deleted.Field Update on 01/14/2002, 1 field added/edited/deleted.Field Update on 08/08/2001, 1 field added/edited/deleted.Field Update on 05/15/2001, 1 field added/edited/deleted.Complete Update on 10/18/2000, 4 fields added/edited/deleted.Field Update on 06/12/2000, 1 field added/edited/deleted.Field Update on 06/12/2000, 1 field added/edited/deleted.Field Update on 02/08/2000, 1 field added/edited/deleted.Field Update on 02/02/2000, 1 field added/edited/deleted.Field Update on 09/21/1999, 1 field added/edited/deleted.Field Update on 08/26/1999, 1 field added/edited/deleted.Field Update on 06/03/1998, 1 field added/edited/deleted.Field Update on 03/10/1998, 1 field added/edited/deleted.Field Update on 11/01/1997, 1 field added/edited/deleted.Complete Update on 02/03/1997, 1 field added/edited/deleted.Complete Update on 05/14/1996, 1 field added/edited/deleted.Complete Update on 02/01/1996, 1 field added/edited/deleted.Complete Update on 01/12/1995, 1 field added/edited/deleted.Complete Update on 11/28/1994, 1 field added/edited/deleted.Complete Update on 06/07/1994, 50 fields added/edited/deleted.