Tebufenpyrad

333.86

333.86

601-585-0

IRU3P7ZB3F

DTXSID0034223

Off-white solid

2933199012

46.92000

3.90

1.1±0.1 g/cm3

61.5 °C

468.4±45.0 °C at 760 mmHg

237.1±28.7 °C

1.565

7.79e-06 M|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

0-6°C

5.99E-09mmHg at 25°C

Oral-rat LD50: 595 mg/kg; inhalation-rat LC50: 2660 mg/m3

Flammable; decomposes toxic hydrogen chloride, nitrogen oxide gas

Slight aromatic odor|Weak halide /Technical product/

Henry's Law constant = <1.2X10-8 atm-cu m/mol at 25 °C (est)

191.25 Ų [M+H]+ [CCS Type: TW]|193.63 Ų [M+H]+

III

6.1(b)

2588

22

36

UQ6276400

Xn

Warehouse low temperature, ventilated, dry

H302

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.

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]

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P314, P321, P330, P333+P313, P363, P391, P405, and P501|H301 (86.01%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P321, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 293 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501

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/

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.

moderately toxic

LD50 Rat (male) oral 595 mg/kg|LD50 Rat (female) oral 997 mg/kg|LD50 Mouse (male) oral 224 mg/kg|LD50 Mouse (female) oral 210 mg/kg|LD50 Rat dermal >2000 mg/kg

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

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 is reported stable to hydrolysis at pH 4, 7 and 9(1). Tebufenpyrad has an aqueous photolysis half-life of 187 days at pH 7 and 25 °C(1).

14.13|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).

Koc values of 1380 to 9310 have been reported for tebufenpyrad(1). According to a classification scheme(2), this Koc range suggests that tebufenpyrad is expected to have low to no mobility in soil.

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).

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).

Occupational exposure to tebufenpyrad may occur through inhalation and dermal contact with this compound at workplaces where tebufenpyrad is produced or used. Limited monitoring data indicate that the general population may be exposed to tebufenpyrad via ingestion of food. (SRC)

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.

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.

...Tebufenpyrad is a powerful and specific inhibitor of /mitochondrial/ complex I

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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/

4-chloro-N-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide

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.

The WHO Recommended Classification of Pesticides by Hazard identifies tebufenpyrad (technical grade) as Class II: moderately hazardous; Main Use: miticide.

The active substance in technical grade material is determined by gas chromatography with flame ionization detector. Residues in plants, soil and water are determined by liquid chromatography-mass spectrometry or gas chromatography-mass spectrometry.

Agrochemicals -> Acaricides|Acaricides|Environmental transformation -> Pesticides (parent, predecessor)

Tebufenpyrad has known environmental transformation products that include CL 810,719, CL 810,721, CL 810,728, CL 810,729, and CL810,723.