Tetraconazole

372.15

372.15

407-760-6

DTXSID8034956

Colorless, viscous liquid

39.9

3.56

1.432 at 20 deg C

6 °C

Decomposes at 240 deg C without boiling

219.0±31.5 °C

1.544

In water, 150 mg/L at 20 deg C

0-6°C

1.8 x l0 -4 Pa

LD50 orally in rats: 1150 mg/kg (Garavaglia)

Henry's Law constant = 4.23X10-9 atm-cu m/mol at 25 °C (est)

174.34 Ų [M+H]+ [CCS Type: TW]|178.08 Ų [M+Cl]-

Yellow to yellowish-brown liquid /Technical/|Hydroxyl radical reaction rate constant = 1.09X10-11 cu cm/molec-sec at 25 °C (est)

UN 3082 9 / PGIII

3

20/22-40-51/53

36/37-41-61-36

Xn,N

P273

H302 + H332-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|PESTICIDE DISPOSAL: Wastes resulting from the use of this product may be disposed of on-site or at an approved waste disposal facility. CONTAINER DISPOSAL: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or incinerate, or if allowed by state and local authorities, by burning. If burned, stay out of smoke.|For bulk and mini-bulk containers (4000 gal. tanker truck and 260 gal. totes), ...when the container is empty, replace the cap and seal all openings that have been opened during use; and return to the point of purchase, or to a designated location named at the time of purchase of this product. This container must only be refilled with this pesticide product. Do Not Reuse the Container for Any Other Reason. Prior to refilling, inspect carefully for damage such as cracks, punctures, abrasions, worn-out threads and closure devices. Check for leaks after refilling and before transporting. Do not transport if this container is damaged or leaking. If the container is damaged or leaking, call Chem-Trec. /Eminent 125SL Fungicide/|Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or other waters unless in accordance with the requirements of.a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment authority. For guidance contact your State Water Board or Regional Office of the EPA.

USEPA Office of Prevention, Pesticides, and Toxic Substances; Pesticide Fact Sheet for Tetraconazole 36 pp. (April 2005) was issued to provide information on EPA's decision to register this chemical as a new pesticide.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 79 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302+H332 (17.92%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|Aggregated GHS information provided by 212 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

Applicators and other handlers must wear: long sleeved shirt and long pants, shoes plus socks, and chemical-resistant gloves. Some materials that are chemical-resistant to this product are barrier laminate, butyl rubber 14 mils, nitrile rubber 14 mills, polyvinyl chloride (PVC) 14 mils, and viton 14 mills. If you want more options, follow the instructions for category C on an EPA chemical-resistance category selection chart. /Eminent 125SL Fungicide/|Use this product /for agriultural use/ only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170... Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. For early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, wear: coveralls, chemical-resistant gloves, and shoes plus socks. /Eminent 125SL Fungicide/

If the container is damaged and leaking or material has been spilled, follow these procedures: Cover spill with absorbent material. Sweep into disposal container. Wash area with detergent and water and follow with clean water rinse. Do not allow to contaminate water supplies. Dispose of according to instructions. /Eminent 125SL Fungicide/

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.|Avoid contact with eyes, skin, and clothing. Wash thoroughly with soap and water after handlingand before eating, drinking, chewing gum, or using tobacco. /Eminent 125SL Fungicide/|Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. /Eminent 125SL Fungicide/|Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Eminent 125SL Fungicide/|For more Preventive Measures (Complete) data for TETRACONAZOLE (8 total), please visit the HSDB record page.

Causes moderate eye irritation /Tetraconazole technical/

LD50 Rat (male) oral 1030 mg a.i./kg bw|LD50 Rat (female) oral 1248 mg a.i./kg bw

/BIRDS and MAMMALS/ Two bobwhite quail studies were submitted in conjunction. Based on these two studies the NOAEC and LOAEC values are 12 and 25 mg/kg diet, respectively, for reproduction. In the first study the percentage of 14-day old survivors of eggs set and 14-day old survivor weight were significantly reduced at all treatment levels; the LOAEC was determined to be 25 mg/kg diet. In the second study no effects were noted at 6 or 12 mg/kg diet, therefore 12 mg/kg diet was determined to be the NOAEC value. ...|/BIRDS and MAMMALS/ ...In the mallard duck study there were reductions in the percentage of 14-day old survivors of normal hatchlings (14%), hatchling weight (10%), and 14-day old survivor weight (11%) at the 50 mg/kg diet treatment levels. At the 100 mg/kg diet treatment level, there were also statistically significant reductions in the female body weight (7%), number of eggs laid (55%), egg shell thickness (10%), proportion of viable embryos (56%), proportion of 3-week live embryos (59%), number of normal hatchlings (69%), number of 14 days old survivors (89%), hatchling weight (14%) and 14-day old survivor weight (31%). The NOAEC and LOAEC were determined to be 10 and 50 mg/kg diet, respectively. This study indicates that tetraconazole exposures of 50 mg/kg diet to the mallard duck may result in serious adverse reproductive effects.|/AQUATIC SPECIES/ A freshwater fish early-life stage toxicity study was submitted /to EPA's Office of Pesticides/ for tetraconazole using the fathead minnow (Pimephales promelas). ...Hatching success was significantly reduced at 3.1 mg a.i./L (LOAEC) compared to solvent control. Post-hatch survival was also statistically reduced at 3.1 mg a.i./L (LOAEC). The calculated 28-day LC50 (with 95% C.I.) was 3.3 (2.7-4.4) mg a.i./L. The NOAEC for alevin/fry mortality was 0.96 mg a.i./L. The percentage of observed sub-lethal effects (small and thin) was highest in the 3.1 mg a.i./L treatment group compared to all other groups after 14-28 days post-hatch. Terminal growth measured by length and dry weight was significantly reduced, in which the NOAEC was 0.30 mg a.i./L and the LOAEC was 0.96 mg a.i./L.|/AQUATIC SPECIES/ Four freshwater fish toxicity studies /(using bluegill sunfish (Lepomis macrochirus) and rainbow trout (Orcorhynchus mykiss))/ were submitted /to EPA's Office of Pesticides/ with reported LC50's 3.85, 3.91, >3, and >5.2 mg a.i./L, which classifies tetraconazole as moderately toxic to freshwater fish on an acute exposure basis. ...Sublethal effects in all four studies were similar and included increased pigmentation, loss of equilibrium, fish at the bottom of the test chamber, and/or distended abdomen.|For more Ecotoxicity Excerpts (Complete) data for TETRACONAZOLE (9 total), please visit the HSDB record page.

Tetraconazole's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 531 through 1,922(2) indicates that tetraconazole is expected to have low mobility in soil(SRC). Volatilization of tetraconazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.35X10-6 mm Hg(2), and water solubility, 156 mg/L(2). Tetraconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation data were not available(SRC, 2008).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 531 through 1,922(2) indicates that tetraconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.3X10-6 mm Hg(2), and water solubility, 156 mg/L(2). According to a classification scheme(4), an estimated BCF of 110(SRC), from its log Kow of 3.56(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism. Biodegradation data were not available(SRC, 2008).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetraconazole, which has a vapor pressure of 1.35X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tetraconazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 35 hours(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tetraconazole may be removed from the air by wet or dry deposition(SRC). Tetraconazole is stable in light(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of tetraconazole with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 35 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tetraconazole is not expected to undergo hydrolysis in the environment as it has been reported to be stable in dilute aqueous solutions at pH 5-9(2). Tetraconazole is stable in light(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).|Tetraconazole exhibited half-lives of 5.7 and 5.1 days on leaves at low and high recommended application levels of 0.05 and 0.10 kg active ingredient/ha, respectively, to experimental field plots of sugar beets; half-lives of 5.7 and 5.2 days, respectively, were noted in the roots; detection limits of 0.002 mg/kg (foliage) and 0.001 mk/kg (roots)(1).

An estimated BCF of 110 was calculated in fish for tetraconazole(SRC), using a log Kow of 3.56(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

A Koc range for tetraconazole of 531 through 1,922 in four soil types has been reported(1). According to a classification scheme(2), this Koc range suggests that tetraconazole is expected to have low mobility in soil.

The Henry's Law constant for tetraconazole is estimated as 4.2X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 1.35X10-6 mm Hg(1), and water solubility, 156 mg/L(1). This Henry's Law constant indicates that tetraconazole is not expected to volatilize from water surfaces(2). Tetraconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to tetraconazole may occur through inhalation and dermal contact with this compound at workplaces where tetraconazole is produced or used. (SRC)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

Two Crl:CD rats/sex/group were dosed orally by gavage with 5 or 60 mg/kg of Triazole-14C-ASC-66811 (M14360) (radiochemical purity: >99%, specific activity: 42 mCi/mmole). Unlabelled ASC-66811 (purity: 99.7%) was used to adjust the specific activity of the dosing preparations. Urine, carbon dioxide, and fecal samples were collected at designated intervals up to 168 hours post-dose. The distribution of radiolabel in the tissues was examined at 168 hours post-dose. Excretion via the urine was the primary pathway with 79 to 95% of the administered radiolabel recovered in the urine. Twelve to 16% of the radiolabel was recovered in the feces. At the lower dosing level, 61 and 27% of the administered dose was excreted within the 1st 24 hours post-dose for the males and females, respectively. At the higher dose, 28 and 8% of the dose was excreted during the 1st 24 hours for the males and female, respectively. Recovery of the radiolabel in the exhaled air ranged from 0.13 to 0.23% of the administered dose for both dose levels. The residual radiolabel in the tissues ranged from 0.7 to 1.9% of the administered dose. The radiolabel was not sequestered in a particular tissue at 7 days post-dose.|Two Crl:CD rats/sex/group were dosed orally by gavage with 5 or 60 mg/kg of [U-14C-phenyl]-ASC-66811 (M14360) (radiochemical purity: 99.3% (TLC), 99.0% (HPLC)). Unlabelled ASC-66811 (purity: 94.0%) was used to adjust the specific activity of the dosing preparations. Urine, carbon dioxide, and fecal samples were collected at designated intervals up to 168 hours post-dose. The distribution of radiolabel in the tissues was examined at 168 hours post-dose. Excretion via the urine was the primary pathway with 70 to 79% of the administered radiolabel recovered in the urine. Twenty one to 32% of the radiolabel was recovered in the feces. At the lower dosing level, 70 and 57% of the administered dose was excreted within the 1st 24 hours post-dose for the males and females, respectively. At the higher dose, 64 and 21% of the dose was excreted during the 1st 24 hours for the males and female, respectively. Recovery of the radiolabel in the exhaled air was minimal. The residual radiolabel in the tissues constituted <1% of the dose. The kidneys were the primary site of recovery at 7 days post-dose.|Three Crl:CD BR rats/sex/group were dosed orally by gavage with 5 or 60 mg/kg of (14C)-Phenyl M 14360 (radiochemical purity: 96.90%, specific activity: 37.35 mCi/mmole). Unlabeled M 14360 technical (purity: 97.6%) was used to adjust the specific activity of the dosing preparations. One animal/sex was dosed with the vehicle alone. Blood was drawn at specified times post-dose from each of the study animals. The radiolabel recovered from each sample was determined by combustion of the sample and recovery of the radiolabeled carbon dioxide which was then analyzed by liquid scintillation counting. The maximal blood concentration of the radiolabel could not be determined because the highest level of radioactivity was recorded for the first sample time in each of the treatment groups. The reported half-lives for the radiolabel in the blood were comparable for all of the treatment groups with a mean for all of the groups of 16.3 hours. Likewise the rates of elimination were comparable with the mean value being 0.044 ng equivalents/g/hour.|Five Crl:CD BR rats/sex/group were dosed orally by gavage with 5 or 60 mg/kg of (14C)-Phenyl M 14360 (radiochemical purity: 97.99%, specific activity: 37.33 mCi/mmole). Unlabeled M 14360 (purity: 97.6%) was used to adjust the specific activity of the dosing preparations. Two animals/sex were dosed only with the vehicle. Urine, feces and cage wash samples were collected from each of the groups at designated time intervals after treatment. The animals were euthanized at 72 hours post-dose. The time-to-peak blood levels for the radiolabel ranged from 1.2 hours post-dose for the 5 mg/kg males to 19.2 hours post-dose for the 60 mg/kg females. The half-life in the blood was approximately 15 hours for all of the treatment groups. The urine was the primary pathway of excretion with 62 to 70% of the administered dose being recovered in the urine and cage wash by 72 hours post-dose for both treatment levels. The recovery in the feces from these groups ranged from 25 to 36%. At 72 hours post-dose, 2.8 to 5.8% of the administered dose was recovered in the tissues. The gastrointestinal tract and the liver were the primary sites of recovery.|For more Absorption, Distribution and Excretion (Complete) data for TETRACONAZOLE (10 total), please visit the HSDB record page.

Three Sprague-Dawley rats/sex were dosed orally by gavage with 1.25 mg/kg of (14C-U-triazolyl) tetraconazole (radiochemical purity: 96.34%, specific activity: 41.72 uCi/mg). Unlabeled tetraconazole was used to adjust the specific acitivity of the dosing preparation to 50 uCi/kg. Urine and feces were collected at specific time intervals up to 72 hours post-dose. Urine was the primary route of excretion with 71 and 62% of the administered dose recovered there for the males and females, respectively. An additional 19 and 26% was recovered in the feces of the males and females respectively. The primary metabolite recovered in the urine was triazole (64 and 41% for the males and females, respectively). Beta-glucuronidase-mediated hydrolysis of the urine samples did not greatly alter the metabolic profile. Unmetabolized tetraconazole was the primary radiolabeled moiety recovered in the feces of the females, 8.8% of the administered dose. M14360-DCP-3OH was the primary metabolite in the feces of the males, 3.5% of the administered dose, followed by triazole (1.9%) and M14360-DCP-5OH (1.2%). In the Experimental Addendum..., M14360-DFA was identified in the urine of the female rats. This recovery constituted 1.2% of the administered dose.|Pooled urine and fecal samples derived from the first 48 hours post-dose of both single dose and multiple dose treatment regimens in which Crl:CD BR rats of both sexes were dosed orally by gavage with 5 or 60 mg/kg of (14C)-Phenyl M 14360 (radiochemical purity: 97.99%, specific activity: 37.33 mCi/mmole)... were analyzed for radiolabeled metabolites by means of GC/MS. Oxidation and reduction of the parent compound resulted in the recovery of the M 14360 acid in the urine and the M14360 alcohol in the feces of both sexes at both treatment levels for both treatment regimens. Displacement of the triazole ring from the parent compound by glutathione and subsequent metabolism resulted in the recovery of the sulfoxide (P1) and the N-acetylcysteine (P4) conjugates. P1, P4 and M 14360 acid were recovered in the urine. P4, M 14360 and M 14360 alcohol were recovered in the feces. Additional metabolites, P2 and P3, were recovered in the urine and P5 was isolated in the feces. The structures of these moieties were not elucidated. The unidentified radiolabeled moieties constituted 15 to 33% of the administered dose for both treatment levels under both treatment regimens.|... Triazole was the major metabolite identified in the urine and feces. In the urine M-14360 acid along with minor metabolite of M-14360 alcohol and its glucuronide conjugate (M3) were isolated. In the feces minor amounts of parent M-14360, the acid and alcohol were isolated. ...|Tetraconazole results in the formation of /1,2,4-triazole (T), triazolyl alanine (TA), triazolyl acetic acid (TAA)/ as well as /triazolyl hydroxypropionic acid/ (THP).|For more Metabolism/Metabolites (Complete) data for TETRACONAZOLE (6 total), please visit the HSDB record page.

16.98 Days

/SIGNS AND SYMPTOMS/ Harmful if swallowed or absorbed through skin. Causes moderate eye irritation. /Tetraconazole technical/|/GENOTOXICITY/ Hela S3 cells were exposed to M 14360 technical (purity: 94.6%) at concentrations ranging of 0.25 to 512 ug/mL for 3 hours at 37 °C under conditions of non-activation and activation. Two trials were performed with duplicate plates for each treatment level. An S9 fraction derived from the liver of rats pretreated with Aroclor 1254 was used to metabolize the test material. There was no apparent treatment-related increase in the net grain count under conditions of either nonactivation or activation.

1H-1,2,4-triazole, 1-(2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl)-

Emulsifiable concentrate, oil-in-water emulsion, liquid for seed treatment.|TETRACONAZOLE TECHNICAL: Active Ingredient 97% Tetraconazole.|EMINENT 125SL FUNGICIDE: Active Ingredient 11.6% Tetraconazole.|For more Formulations/Preparations (Complete) data for TETRACONAZOLE (6 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Tetraconazole (technical grade) as Class II: moderately hazardous; Main Use: fungicide.|... /Acts/ mainly on the vegetative stages of the fungi by blocking the mycelial growth both inside and outside the host plant|Tetraconazole is categorized as a triazole systemic fungicide. The triazoles primarily function by interfering with cell growth, particularly the ability to build cell walls. These fungicides arrest ergosterol biosynthesis in cell membranes. Due to its widespread use to fight fungal diseases in agriculture, the issue of resistance to triazoles has emerged. New compounds, such as tetraconazole, have been developed that are active against resistant organisms.|...Tetraconazole, is marketed in its racemic form, an equal mixture of (+)- and (-) Tetraconazole. However, there is a difference in the level of activity against fungi when individual enantiomers of a racemic mixture of triazole compounds are compared. /It was shown/ ...that (+)Tetraconazole was five times more potent in inhibiting the catalytic activity of the fungal pathogen, C. albicans CYP51, than (-)Tetraconazole. ... The difference in the bioactivity of the tetraconazole enantiomers was not provided for the mode of action or toxicity studies for this screening assessment.

Agrochemicals -> Fungicides

Tetraconazole has known environmental transformation products that include 1H-1,2,4-triazol-1-ylacetic acid.