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rac-1-[(R*)-2-(2,4-ジクロロフェニル)-3-(1,1,2,2-テトラフルオロエトキシ)プロピル]-1H-1,2,4-トリアゾール

Tetraconazole

HCID 80277
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
112281-77-3
標準SMILES
FC(F)C(F)(F)OCC(Cn1cncn1)c1ccc(Cl)cc1Cl
InChIKey
LQDARGUHUSPFNL-UHFFFAOYSA-N
分子式
C13H11Cl2F4N3O
平均分子量
372.14 g/mol
単同位体質量
371.02153

概要

1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole is a member of the class of triazoles that is 1,2,4-triazole substituted at position 1 by a 2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl group. It is a dichlorobenzene, an ether, a member of triazoles and an organofluorine compound.

名称と識別子

優先名称
Tetraconazole
IUPAC
1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1,2,4-triazole
現地名
rac-1-[(R*)-2-(2,4-ジクロロフェニル)-3-(1,1,2,2-テトラフルオロエトキシ)プロピル]-1H-1,2,4-トリアゾール
英語名
Tetraconazole
分子式
C13H11Cl2F4N3O
分子量
372.15

名称と別名

Tetraconazole112281-77-3EminentDomarkDTXSID8034956AG 4454LOSPEL8FGY868T0G1H-1,2,4-Triazole, 1-(2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl)-M 14360DTXCID60149561-(2-(2,4-Dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl)-1H-1,2,4-triazole
名称をさらに表示
テトラコナゾールサルバトーレrac-1-[(R*)-2-(2,4-ジクロロフェニル)-3-(1,1,2,2-テトラフルオロエトキシ)プロピル]-1H-1,2,4-トリアゾールホクガード(RS)-2-(2,4-ジクロロフェニル)-3-(1H-1,2,4-トリアゾール-1-イル)プロピル=1,1,2,2-テトラフルオロエチル=エーテルテトラコナゾール標準品テトラコナゾル(RS)-2-(2,4-ジクロロフェニル)-3-(1H-1,2,4-トリアゾール-1-イル)プロピル=1,1,2,2-テトラフルオロエチル=エーテル (別名 テトラコナゾール)CS_N-13538-100MG_テトラコナゾールテトラコナゾール STANDARDテトラコナゾール標準物質テトラコナゾール Standard, 100 µg/mL in MethanolボンジョルノハナガードTetraconazole@1000 μg/mL in AcetonitrileARPEGEARBITRE

物性

構造計算による物性

XLogP
4.4
極性表面積
39.9 Ų
水素結合供与体数
0
水素結合受容体数
7
回転可能結合数
7
重原子数
23
形式電荷
0
複雑度
381

実験および物理化学的性質

PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
Pesticides · 4 件

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticide (Tetraconazole) -> USDA PDB

Pesticide

LogP · 2 件

log Kow = 3.56

3.53

Density1.432 at 20 °C
Color/FormColorless, viscous liquid
Solubility · 2 件

Readily soluble in 1,2-dichloroethane, acetone, and methanol

In water, 150 mg/L at 20 °C

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling PointDecomposes at 240 °C without boiling
DecompositionDecomposition at 240 °C (boiling point) /from table/
Melting PointPour point 6 °C
Vapor Pressure1.35X10-6 mm Hg at 20 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302+H332 (89.9%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Regulation (EC) No 396/2005 (amended)

Tetraconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2009/82/EU, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/2592, Reg. (EU) No 540/2011

REACH registered substance: (+/-) 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazole-1-yl)propyl-1,1,2,2-tetrafluoroethylether (EC: 407-760-6)

Tetraconazole: Does not have an individual approval but may be used under an appropriate group standard

Special ReportsUSEPA 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.
FIFRA RequirementsTolerances are established for residues of the fungicide, tetraconazole, 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole in or on the following commodities: [Table#7307]
Hazard Classes and Categories · 5 件

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

Skin, Eye, and Respiratory Irritations

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

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. ...

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Hsdb 7612
Arpege(TM)
etraconazole
AG-44541-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl-1,1,2,2-tetrafluoroethyletherM-14360RefChem:896828CHEBI:81782(rs)-2-(2,4-dichlorophenyl)-3-(1h-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether407-760-6

データベース識別子

CAS
112281-77-3
PubChem CID
80277
DTXSID
DTXSID8034956
ChEMBL
CHEMBL2137654
ChEBI
CHEBI:83999
UNII
8FGY868T0G
EC Number
407-760-6、691-058-1
Ionization Efficiency · 6 件

Positive

3.7

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

物理化学的性質

融点
6 °C · 6 °C
沸点
438.4 · 438.4±55.0 °C(Predicted)
比重(密度)
1.5 · 1.50±0.1 g/cm3(Predicted)
蒸気圧
1.8 x · 1.8 x l0-4 Pa
貯蔵温度
0 · 0-6°C
水溶解度
156 mg · 156 mg l-1 (pH 7、ZO °C)
酸解離定数(Pka)
2.68 · 2.68±0.10(Predicted)
外見
Viscous Liquid
色
Colorless to light yellow
Henry's Law Constant
2.3 · 2.3×103 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
農業洗浄剤化粧品環境食品および飲料パーソナルケア
InChI
1S/C13H11Cl2F4N3O/c14-9-1-2-10(11(15)3-9)8(4-22-7-20-6-21-22)5-23-13(18,19)12(16)17/h1-3,6-8,12H,4-5H2
InChIKey
LQDARGUHUSPFNL-UHFFFAOYSA-N
SMILES
FC(F)C(F)(F)OCC(Cn1cncn1)c2ccc(Cl)cc2Cl
LogP
3.56 · 3.560
EPAの化学物質情報
Tetraconazole (112281-77-3)
Causes moderate eye irritation /Tetraconazole technical/

安全と保護具

Storage Conditions · 2 件

Store in sealed original containers, in well aired, fresh, dry storehouse or in shaded and possibly well aired places. Do not contaminate water, food, or feed by storage or disposal. Do not reuse container.

Do not contaminate water, food, or feed byV storage or disposal. Store unused /pesticide/ in original container only in a cool, dry area out of the reach of children or animals.

Cleanup Methods · 1 件

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/

Disposal Methods · 4 件

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.

Preventive Measures · 5 件

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.

Allowable TolerancesTolerances are established for residues of the fungicide, tetraconazole, 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole in or on the following commodities: [Table#7306]
Personal Protective Equipment (PPE) · 2 件

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/

毒性情報

Ecotoxicity Values · 5 件

LD50 Anas platyrhynchos (Mallard duck) oral 131 mg/kg bw /from table/

LD50 Colinus virginianus (Bobwhite quail) oral 131 mg a.i./kg bw

LC50 Anas platyrhynchos (Mallard duck) diet 382 mg a.i./kg-diet/5 days /from table/

LC50 Colinus virginianus (Bobwhite quail) diet 637 mg/kg diet/5 days

For more Ecotoxicity Values (Complete) data for TETRACONAZOLE (16 total), please visit the HSDB record page.

Environmental Fate · 3 件

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).

Ecotoxicity Excerpts · 5 件

/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.

Soil Adsorption/MobilityA 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.
Human Toxicity Excerpts · 2 件

/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.

Artificial Pollution SourcesTetraconazole'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).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 件

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).

Volatilization from Water/Soil · 1 件

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).

Non-Human Toxicity Excerpts · 5 件

/LABORATORY ANIMALS: Acute Exposure/ Tetraconazole has low acute toxicity (EPA Toxicity category III or IV) via the oral, dermal, and inhalation routes. It is a slight eye irritant, but is not a dermal irritant or a dermal sensitizer.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Five Crl:CD rats/sex/group were dosed orally by gavage with 0, 70, 200 or 500 mg/kg/day of M 14360 Technical (purity: 92%) for 4 weeks. All of the animals in the 500 mg/kg group and 3 females in the 200 mg/kg group were euthanized for moribundity within 3 days of the study initiation. A fourth female was euthanized during the 3rd week due to moribundity as well. The mean body weight of the males in the 200 mg/kg group was less than that of the controls through out the treatment period. The hematology data did not indicate an apparent treatment-related effect. In the clinical chemistry evaluation, the mean serum glucose levels were lower for both sexes in the 70 mg/kg group and for the males in the 200 mg/kg group (p<0.01 or 0.001). The total protein and albumin levels of the males in the 70 and 200 mg/kg group were greater than that of the control (p<0.05 or 0.01). The globulin levels for the 70 mg/kg females and the 200 mg/kg males were increased as well (p<0.01). In the necropsy examination, the mean liver weights were increased for both sexes in the 70 mg/kg group and for the males in the 200 mg/kg group (the one survivor among the females in the 200 mg/kg group also had an increased liver weight) (p<0.01). Target tissue: liver; The presence or absence of adverse effects was not determinable due to the lack of histopathology, particularly on the liver. 4-Week Rat Oral Toxicity NOEL: < 70 mg/kg/day (based upon the effects on the liver and the serum glucose levels of both sexes in the 70 mg/kg/day group).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Ten Crl:CD rats/sex/group received 0, 40, 160, 640, 2500 or 10000 ppm of M 14360 Technical (purity: 92%) in the diet for 4 weeks ((M) 0, 4.4, 17.5, 68.4, 229 mg/kg/day, (F) 0, 3.8, 16.0, 62.3, 217 mg/kg/day). All of the animals in the 10000 ppm group were euthanized in moribund condition within 5 days of the study initiation. The mean body weight gains for both sexes in the 2500 ppm group and the females in the 640 ppm group through out the study were less than those of the controls (p<0.01). The food consumption for these animals was less than that of the controls over this period. The hematology data did not indicate an apparent treatment-related effect. In the clinical chemistry evaluation, the serum glucose levels for both sexes in the 2500 ppm group and the males in the 640 ppm group were less than that of the controls (p<0.05 or 0.01). The total protein and globulin levels in the serum of the males in the 640 and 2500 ppm groups were greater than those of the controls (p<0.05 or 0.01). The mean absolute and relative liver weights of the 40 ppm males and above and the 640 and 2500 females were greater than that of controls (p<0.05 or 0.01). The mean relative kidney weights of the 40 ppm males and above and the 160 ppm females and above were greater than that of the controls (p<0.05 or 0.01). In the histopathological examination, a dose-related enlargement of centrilobular to midzonal hepatocytes in the liver of both sexes of the 160 ppm group and above was noted ((M) 0: 0/10 vs. 160: 3/10, 640: 8/10, 2500: 10/10, (F) 0: 0/10 vs. 160: 5/10, 640: 10/10, 2500: 10/10). The livers of both sexes in the 2500 ppm group exhibited fine vacuolation of centrilobular to midzonal hepatocytes ((M) 0: 0/10 vs. 2500: 8/10, (F) 0: 0/10 vs. 2500: 6/10). Target organ: liver. ...4- Week Rat Dietary NOEL: (M/F) 40 ppm ((M) 4.4 mg/kg/day, (F) 3.8 mg/kg/day) (based upon the enlargement of hepatocytes in the livers of both sexes in the 160 ppm group).

Evidence for Carcinogenicity · 2 件

Cancer Classification: Likely to be Carcinogenic to Humans

Tetraconazole was classified as likely to be carcinogenic to humans based on the occurrence of liver tumors in male and female mice. The Carcinogenicity Assessment Review Committee recommended that a low dose extrapolation model be applied to the experimental animal tumor data and that quantification of risk be estimated for male and female mouse liver tumors for Tetraconazole. The most potent unit risk will be used for the purpose of lifetime cancer risk assessment by the Agency. In this case, the most potent unit risk, Q1*, is that for male mouse liver benign and/or malignant combined tumor rates at 2.30 x 10-2 in human equivalents.

Environmental Abiotic Degradation · 2 件

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).

法規制情報

FIFRA RequirementsTolerances are established for residues of the fungicide, tetraconazole, 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole in or on the following commodities: [Table#7307]

安全データ

wgk
3
ridadr
UN 3082 9 / PGIII
毒性
LD50 orally in rats: 1150 mg/kg (Garavaglia)
PRTR法
第1種指定化学物質
risk_code
20/22-40-51/53
hazard_code
Xn,N
safety_code
36/37-41-61-36
Hazard Classifications
Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 2
ストレージクラス
10 - Combustible liquids
有毒物質データの
112281-77-3(Hazardous Substances Data)

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.

MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Absorption, Distribution and Excretion · 5 件

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.

用途と製造

Uses · 4 件

For tetraconazole (USEPA/OPP Pesticide Code: 120603) 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./

Fungicide; Foliar spray in blueberries, cereals, grapes, ornamentals, peanuts, pome fruits, sugarbeets, vegetables, and as a seed treatment. Effective against Erysiphales, Puccinia, Uromyces, Cercospora beticola, and Venturia.

Agricultural fungicide

This is a man-made compound that is used as a pesticide.

Formulations/Preparations · 5 件

Emulsifiable concentrate, oil-in-water emulsion, liquid for seed treatment.

TETRACONAZOLE TECHNICAL: Active Ingredient 97% Tetraconazole.

EMINENT 125SL FUNGICIDE: Active Ingredient 11.6% Tetraconazole.

TETRACONAZOLE TECHNICAL: Active Ingredient 97% Tetraconazole.

For more Formulations/Preparations (Complete) data for TETRACONAZOLE (6 total), please visit the HSDB record page.

General Manufacturing Information · 4 件

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.

応用分野

用途農薬(殺菌剤)

使用Tetraconazole is an conazole fungicide used to control pests in apple and strawberries.

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/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Ten Crl:CD male rats/group received 0, 2, 5, 15 or 40 ppm of M 14360 Technical (purity: 90.9% (8/10/87), 90.4% (1/26/88)) in the diet for 4 weeks (0, 0.21, 0.52, 1,57, 4.19 mg/kg/day). No deaths resulted from the treatment. The mean body weights and food consumption were not affected by the treatment through out the study. Although the serum GOT and GDH activities of the 40 ppm group were elevated above those of the control, these effects were not toxicologically significant. There were no treatment-related effects upon liver weights or the incidence of lesions in the liver. ...4-Week Rat Dietary NOEL: (M) 40 ppm (4.2 mg/kg/day) (based upon the lack of treatment-related effects at the highest dose tested).

For more Non-Human Toxicity Excerpts (Complete) data for TETRACONAZOLE (20 total), please visit the HSDB record page.