4-クロロ-2-メチル-5-エチル-N-(4-tert-ブチルベンジル)-2H-ピラゾール-3-カルボアミド

Pesticides

Acaricides

Active substance -> EU Pesticides database: Approved

Pesticides -> Other Insecticides

Acaricides

Environmental transformation -> Pesticides (parent, predecessor)

log Kow = 4.93 at 25 °C

4.61

Slight aromatic odor

Weak halide /Technical product/

1.0214 g/cu cm

Density = 0.5 g/mL at 24.1 °C /Technical product/; 8.71 lbs/gal /End-use product/

In water, 2.61 mg/L at 25 °C

Solubility in water = 2.61 ppm at pH 5.9, 3.21 ppm at pH 4, 2.39 ppm at pH 7, and 2.32 ppm at pH 10 /Technical product/

Solubility (mg/L at 25 °C): in hexane 255; toluene 772; dichloromethane 1044; acetone 819; methanol 818; acetonitrile 785

178.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Pesticides]

191.25 Ų [M+H]+ [CCS Type: TW]

193.63 Ų [M+H]+

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P317, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (77.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Commission Regulation (EC) No 1490/2002

2009/11, Reg. (EU) 2022/1480, Reg. (EU) 2023/1757, Reg. (EU) No 540/2011

USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Tebufenpyrad, Reason for Issuance: Unconditional Registration (August 26, 2002)[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]

Acute Tox. 3 (77.6%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 3

Acute Tox. 3

Store in cool, dark place.

Do not contaminate water, food or feed by storage or disposal. Do not store in direct sunlight or heat. Keep away from heat, open flame, or sparks. ... Keep out of reach of children and animals. Use with adequate ventilation. Store in original container in a cool. dry place. Replace lid and keep tightly closed after opening. /AC 801,757 3EC Miticide-Insecticide/

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.

Container Disposal: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, by incineration or, if allowed by State and local authorities, by burning. If burned, stay out of smoke. /AC 801,757 3EC Miticide-Insecticide/

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /AC 801,757 3EC Miticide-Insecticide/

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /AC 801,757 3EC Miticide-Insecticide/

Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet; Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing; Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /AC 801,757 3EC Miticide-Insecticide/

Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry. /AC 801,757 3EC Miticide-Insecticide/

For more Preventive Measures (Complete) data for TEBUFENPYRAD (8 total), please visit the HSDB record page.

Chemical resistant gloves. Protective eyewear.

Applicators and other handlers must wear: long-sleeved shirt and long pants; chemical-resistant gloves, such as barrier laminate or Viton (greater than or equal to 14 mils; shoes plus socks. /AC 801,757 3EC Miticide-Insecticide/

/Restricted entry interval (REI) of twelve (12) hours/ PPE required for early entry into 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, is: coveralls; chemical-resistant gloves, such as barrier laminate or Viton (greater than or equal to 14 mils); shoes plus socks. /AC 801,757 3EC Miticide-Insecticide/

LC50; Species: Carp; Concentration: 0.073 mg/L for 48 hr /Conditions of bioassay not specified in source examined/

LD50; Species: Colinus virginianus (Bobwhite quail) oral >2000 mg/kg

LC50; Species: Anas platyrhyncos (Mallard duck) dietary >5000 mg/kg for 8 days

LC50; Species: Colinus virginianus (Bobwhite quail) dietary >5000 mg/kg for 8 days

LC50; Species: Baetis rhodani (Mayfly); Conditions: freshwater, static, 15 °C, pH 7.4, hardness 180 mg/L CaCO3; Concentration: 2.69 ug/L for 48 hr (95% confidence interval: 1.41-5.12 ug/L) /100% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), reported Koc values of 1380 to 8310(2), indicate that tebufenpyrad is expected to have low to no mobility in soil(SRC). Volatilization of tebufenpyrad from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of <1.2X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, <7.3X10-8 mm Hg(3), and water solubility, 2.61 mg/L(2). Tebufenpyrad is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Specific biodegradation data were unavailable, but tebufenpyrad had reported soil dissipation half-lives in laboratory studies of 19 to 56 days and in the field as 2 to 50 days(2).

AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 1380 to 8310(2), indicate that tebufenpyrad 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 <1.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, <7.3X10-8 mm Hg(4), and water solubility, 2.61 mg/L(2). According to a classification scheme(5), an estimated BCF of 830(SRC), from its log Kow of 4.93(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Microbially-mediated degradation has been identified as a major route of dissipation for tebufenpyrad(4). Tebufenpyrad is reported to be stable to hydrolysis at environmental pHs and has an aqueous photolysis half-life of 187 days at pH 7 and 25 °C(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tebufenpyrad, which has a vapor pressure of <7.3X10-8 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tebufenpyrad may be removed from the air by wet or dry deposition(SRC).

Tebufenpyrad residues were detected in 12 of 86 apple samples taken during a study of pesticides in agricultural products in Hyogo Prefecture, Japan from 1995 to 1999. Five of these residues were detected at <0.01 ug/g, five were detected at 0.01 to <0.05 ug/g and two were detected at 0.05 to <0.1 ug/g(1).

/GENOTOXICITY/ /In/ in vitro cytogenetics assays with human lymphocytes tebufenpyrad /at concentrations of/ a)6, 8, 20, 40, 60, 80 ug/mL for 21 hours without activation and 8.25, 11, 27.5, 55, 82.5, 110 ug/mL for 4 hours with activation /or/ b)6.25, 12.5, 25 :g/ml for 2 hours without activation and 12.5, 25 and 50 ug/mL for 3 hours with activation, the combined data from both studies indicate that without S9 activation, tebufenpyrad induced variable but nevertheless reproducible significant increases in the percentage of aberrant cells in two of three experiments using treatment times of 20-24 hours. In general, levels causing < 40% decrease in the MI /mitotic index/ were negative, whereas concentrations causing >42% decrease in the MI induced significant effects with reproducibly flat dose response curves. Furthermore, the same type of aberrations (chromatid breaks) was induced in both studies. Based on these considerations, it is concluded that MK-239 exhibited reproducible but weak evidence of a clastogenic response but only after prolonged exposure to cytotoxic doses and only in the absence of S9 activation. /from table/

An estimated BCF of 830 was calculated in fish for tebufenpyrad(SRC), using a log Kow of 4.93(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).

The Henry's Law constant for tebufenpyrad is estimated as <1.2X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, <7.3X10-8 mm Hg(1), and water solubility, 2.61 mg/L(2). This Henry's Law constant indicates that tebufenpyrad is expected to be essentially nonvolatile from water and moist soil surfaces(3). Tebufenpyrad is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Acute Exposure/ Non-irritating to skin and eyes (rabbits). Sensitizing to skin (guinea pigs).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A uniform picture emerges for 90-day dietary or gavage studies in rats, mice and dogs. The only effects consistently observed were decreased weight gain and increased liver weight at the highest doses (about 28 mg/kg/day in the rat, 160 (M) to 220 (F) mg/kg/day in mice , and 10 mg/kg/day in dogs). Some liver hypertrophy was seen in rats, and vomiting and diarrhea occurred in dogs.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Chronic toxicity in dogs /was studied at doses of/ 0, 1, 6, 20 mg/kg/day. NOAEL in males and females = 1 mg/kg/day; LOAEL = 6 mg/kg/day based on increased incidence of vomiting and diarrhea/loose stools and thickened gastric mucosa and chronic gastritis in the pyloric region. /from table/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Chronic toxicity/carcinogenicity in rats /was studied at doses of/ 0, 5, 20, 150, or 300 ppm (M; 0, 0.21, 0.82, 6.52, 13.43 mg/kg/day: F: 0, 0.26, 1.01, 8.13, 16.95 mg/kg/day). ...Male rats had a significant increasing trend, and a significant difference in the pair-wise comparison of the 300 ppm dose group with the controls, for hepatocellular adenomas, both at p<0.01. The incidence at the high dose (300 ppm) exceeded the historical control range. ...The increase in benign liver tumors /was considered/ to be treatment-related in males. No hepatocellular carcinomas were observed in any group, including controls. Female rats had a significant increasing trend, and a significant difference in the pair-wise comparison of the 150 ppm dose group with the controls, for hepatocellular adenomas, both at p<0.05. However, no dose-related increase in these tumors was noted at the high dose (300 ppm). The incidence at 150 ppm was just outside the historical control range; and the incidence at 300 ppm was within the historical control range. No hepatocellular carcinomas were observed in any group, including controls. /from table/

For more Non-Human Toxicity Excerpts (Complete) data for TEBUFENPYRAD (8 total), please visit the HSDB record page.

Hydroxylations of the ethyl and tert-butyl groups were the predominant reactions both in vitro, using S9 rat liver fraction, and in vivo. Subsequent oxidation of these initial alcohols to carboxylic acids and conjugation of the alcohols with sulfate occurred in vivo.Little cleavage of the amide bond was observed.

The metabolism study in the rat showed that >80% of tebufenpyrad was absorbed from the digestive system within 24 hours. The compound appeared to undergo rapid and extensive first-pass metabolism to primarily hydroxylated or carboxylated products with little of the parent compound appearing in the urine or feces. It was excreted primarily in the feces which accounted for >/=60% of the elimination; however, a significant portion was found in the urine (16-24%). More than 70% of the test material or its metabolites were eliminated within 72 hours of treatment and >90% was eliminated by 7 days. No accumulation of the parent compound or its metabolites was noted.

A slight sex-specific difference in the metabolic disposition of the test material was found with male rats excreting more of the carboxylic acid metabolite on a relative basis while females tended to excrete more of the sulfate conjugate.

Metabolite is N-[4-(1-hydroxymethyl-1-methylethyl)benzyl]-4-chloro-3-(1-hydroxyethyl)-1-methylpyrazole-5- carboxamide.

Metabolites of unlabeled and pyrazole-3-14C-labeled tebufenpyrad, N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide, formed in the in vitro system using 9000 x g supernatant of rat liver homogenate and in vivo system of rats were identified. In the in vitro system, the major metabolites were N-(4-tert-butylbenzyl)-4-chloro-3-(1-hydroxyethyl)-1-methylpyrazole-5-carboxamide ... and N-(4-(1-carboxy-1-methylethyl)benzyl)-4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide ... In the in vivo system, the major metabolite was N(4-(1-carboxy-1-methylethyl)benzyl)-4-chloro- 3 -(1-hydroxyethyl)- 1-methylpyrazole- 5 -carboxamide, which was mainly excreted in urine.

The metabolism study in the rat showed that >80% of tebufenpyrad was absorbed from the digestive system within 24 hours. The compound appeared to undergo rapid and extensive first-pass metabolism to primarily hydroxylated or carboxylated products with little of the parent compound appearing in the urine or feces. It was excreted primarily in the feces which accounted for >/=60% of the elimination; however, a significant portion was found in the urine (16-24%). More than 70% of the test material or its metabolites were eliminated within 72 hours of treatment and >90% was eliminated by 7 days. No accumulation of the parent compound or its metabolites was noted.

...Fish were exposed to 14C-tebufenpyrad treated water (1.2 ug/L) for 28 days, followed by 14 days period for deputation. Bioconcentration factors (BCFs) of 14C reached a steady-state plateau within 7 days of exposure and its maximum BCF was 864. HPLC analysis showed that <4% of the 14C in whole fish was tebufenpyrad to give the maximum BCF of 29. Gall bladder bile contained the highest concentration of 14C, followed by gastrointestinal tract with the contents and liepatopancreas. Tebufenpyrad was not detected in the bile.

Used as acaricide to protect cotton, citrus, fruits, vegetables, and ornamentals; [Merck Index] Registered for use on ornamentals in greenhouses; [Reference #1]

Farming (Pesticides) [Category: Industry]

For tebufenpyrad (USEPA/OPP Pesticide Code: 090102) 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./

Acaricide/Miticide

Tebufenpyrad is registered for use on ornamental plants grown in commercial greenhouses.

Control of all stages of Tetranychus, Panonychus, Oligonychus and Eotetranychus spp.

Trade names: Masai, Pyranica

Emulsifiable concentrate, emulsion oil in water, water dispersible granule, wettable powder.

Trade names: Comanché; Oscar; Acarifas.

Types of Formulations: 98.9% technical product; 34.6% EC /emulsifiable concentrate/ end-use product.

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

Acaricides

Environmental transformation -> Pesticides (parent, predecessor)