Tebufenozide

352.47

352.47

412-850-3

TNN5MI5EKF

DTXSID4034948

Off-white powder

29280000

49.4

4.25 (pH 7)

1.03 (20 deg C, pycrometer method)

191 °C

1.562

In water, 0.83 mg/l @ 25 deg C

0-6°C

3 x 10 -6 Pa (25 °C)

LD50 orally in rats, mice: >5000 mg/kg; dermally in rats: >5000 mg/kg; LD50 in honey bees (96 hr, contact): >234 mg/bee; LC50 in mallard duck (8-day dietary): >5000 mg/kg; LC50 in rainbow trout (96 hr): 5.7 mg/l (Heller)Low toxicity

202.78 Ų [M+Na]+

III

9

UN 3077

2

51/53

61

N

Stable at 94 deg C for 7 days. Stable to light in pH 7 aq soln, (25 deg C). Stable in dark, sterile water 30 days, (25 deg C). DT50 in natural pond water, in light, 30 days (25 deg C).

P273, P391, P501

H411

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.|Warning|H400 (73.58%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|Aggregated GHS information provided by 212 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P314, and P501

LD50 Rat & Mouse oral >5000 mg/kg|LD50 Rat percutaneous >5000 mg/kg|LC50 Rat (male) inhalation >4.3 mg/l/4 hr|LC50 Rat (female) inhalation >4.5 mg/l/4 hr

/OTHER TERRESTRIAL SPECIES/ ...The effects of single and double pulses of Mimic 240 LV (tebufenozide) /were examined/ on the development, growth, and predator avoidance behavior of 4 frog species (wood frogs Rana sylvatica, leopard frogs R. pipiens, green frogs R. clamitans, and bullfrogs R. catesbeiana) exposed in the laboratory as embryos or tadpoles. Nominal doses ranged from 3.0 mg/L to 9.0 mg/L tebufenozide, and exposures were terminated at 96 hr following single, or 192 hr following double, exposures. More than 90% of the animals exposed as embryos hatched. Embryos exposed late in development and subsequently hatching into tebufenozide-contaminated water all hatched and responded normally. Tadpole growth was not delayed following exposure, and premetamorphic green frogs successfully completed metamorphosis following exposure to the highest concn. The results suggest that Mimic 240 LV, when used at the suggested application rates, will not severely affect the aquatic stages of ranid amphibians. /Mimic 240 LV/|/FIELD STUDIES/ The effects of tebufenozide (RH-5992), a potential forest insecticide, on zooplankton communities were determined in 16 littoral enclosures in a small forest lake of northern Ontario. Community structure in enclosures treated with 9, 36, or 157 ug tebufenozide/l ( 0.2, 0.7, and 3 times the expected environmental concn) was compared with natural zooplankton communities in control enclosures. No significant treatment effects on zooplankton communities were detected, even at 3 times the expected environmental concn. While some changes in community structure of crustacean zooplankton in enclosures occurred through the season, these did not appear to be related to the tebufenozide treatments. Tebufenozide residues in water dissipated following exponential decline kinetics with time to 50% dissipation (DT50) ranging from 32-35 days irrespective of initial concn. There were no differences in pH, dissolved oxygen, conductivity, and phytoplankton abundance among treatment levels (repeated-measures ANOVA, p>0.07).

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

TERRESTRIAL FATE: Using a structure estimation method based on molecular connectivity indices(2), the Koc for tebufenozide can be estimated to be 35,000(SRC). According to a classification scheme(1), this estimated Koc value suggests that tebufenozide is expected to have no mobility in soil. A field microcosm study showed that downward movement of tebufenozide in soil occurred only in trace amounts, indicating strong adsorption to the soil(4). Volatilization of tebufenozide from soil surfaces may occur based on results from a laboratory microcosm study; 200 g aliquots of sandy litter, sandy soil, clay litter, and clay soil each containing tebufenozide at a concn of 10 mg/kg were analyzed. The post volatilization residues (mg/kg) in samples kept in darkness at 30 °C for 10 days were 8.89 for sandy litter, 8.29 for sandy soil, 9.02 for clay litter, and 8.45 for clay soil(4). Aquatic studies determined the half-life for photodegradation of tebufenozide by sunlight in surface waters to be 83 hours and therefore, it is expected that photodegradation in surface soils may occur(SRC). Based on aquatic laboratory studies, tebufenozide is stable to hydrolysis under acidic (pH 4) and neutral (pH 7) conditions at 20 °C.(3). Under basic conditions (pH 10) and at 20 °C, the half-life for the reaction was 34 days(3) indicating that tebufenozide may undergo hydrolysis in soil under wet basic conditions. A field microcosm study was conducted to determine dissipation half-lives of tebufenozide in sandy litter and soil. Tebufenozide was applied at 35, 70, and 140 g AI /ha to sandy forest litter (90% OM, 57% sand, 27% silt, 16% clay, pH 5.4) and the corresponding half-lives were 63.1, 62.3, and 115 days respectively. The same amounts applied to the sandy forest soil (3.9% OM, 51% sand, 42% silt, 7% clay, pH 5.9) corresponded to half-lives of 62.2, 62.2, and 52.4 days, respectively, indicating irregular variations in persistence(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 35,000(SRC), determined from a structure estimation method(2), indicates that tebufenozide is expected to adsorb to suspended solids and sediment(SRC). Data from both a field study and a study conducted under controlled laboratory conditions indicate that tebufenozide moved from treated surface water into sediment due to strong adsorption. The laboratory studies showed that total residues in water gradually declined from 14,000 ug/l on day zero to 5,800 ug/l on the 90th day. A field microcosm study was conducted to determine the downward movement of tebufenozide in soil. Tebufenozide was applied as a spray at 35, 70, and 140 g AI /ha to sandy forest soil and samples were collected at intervals up to 408 days after spraying and analyzed for tebufenozide residues. No tebufenozide was detected (LOD, 0.02 ug/g) in soil samples collected from 2.5 - 5.0 cm depth during zero to 85 days post-spray irrespective of the dosage rate. Samples from the plot sprayed at the highest dosage rate contained 0.05 ug/g on the 107th and 408th day post spray. All the other samples (2.5 - 5.0 cm cores) including the ones from 5.0 - 10 and 10 - 15 cm had no detectable amounts of tebufenozide except for the occasional incidence of "trace" amounts. The lack of downward mobility observed in the study could be due to strong adsorption of the tebufenozide onto the sandy soil. Field studies also indicted that tebufenozide would move from the water column and accumulate in the sediment where at 92 days post-spray the residues in the sediment were about 24.5 times higher (the average of 18.4, 19.0, 16.1, and 44.3 times in enclosures treated at 0.05, 0.10, 0.26, and 0.50 mg/l, respectively) than the applied concn levels(7). Disappearance half-lives from the top and middle layers of the sediment were 64 and >90 days, respectively(7). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-8 mm Hg(5), and water solubility, 0.83 mg/l(5). Photodegradation of tebufenozide by sunlight in surface waters was studied and the rate constant and half-life for the reaction were 8.2X10-3/hr and 83 hours, respectively(6). Studies show that tebufenozide was stable in dark, sterilized stream water with a half-life of 734 days(6), but was degraded more rapidly in dark, unsterilized stream water with a half-life of 181 days(6). The difference in degradation rates between the sterilized and unsterilized stream water suggest that microbial processes are a degradative route for tebufenozide in natural aquatic systems(6). Based on aquatic study data, tebufenozide was shown to be stable to hydrolysis under acidic (pH 4) and neutral (pH 7) conditions at 20 °C with half-lives of 1166 and 529 days, respectively. Under basic conditions (pH 10) and at 20 °C, the half-life for the reaction was 34 days(6). According to a classification scheme(4), an estimated BCF of 370(SRC), derived from an experimental log Kow of 4.25(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Data from laboratory microcosm studies have shown the disappearance half-life of tebufenozide from water to be 67 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tebufenozide, which has a vapor pressure of 2.25X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tebufenozide may be removed from the air by wet and dry deposition(SRC).

Based on aquatic study data, tebufenozide was shown to be stable to hydrolysis under acidic (pH 4) and neutral (pH 7) conditions at 20 °C with half-lives of 1166 and 529 days, respectively. Under basic conditions (pH 10) and at 20 °C, the half-life for the reaction was 34 days(1). Photodegradation of tebufenozide by sunlight in surface waters was studied and the rate constant and half-life for the reaction were 8.2X10-3/hr and 83 hours respectively(1).

An estimated BCF of 370 was calculated for tebufenozide(SRC), using a log Kow of 4.25(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tebufenozide can be estimated to be 35,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that tebufenozide is expected to have no mobility in soil. Downward movement in soil using a field microcosm study occurred only in trace amounts, suggesting strong adsorption(3). IN this study, tebufenozide was applied as a spray at 35, 70, and 140 g AI /ha to sandy forest soil and samples were collected at intervals up to 408 days after spraying and analyzed for tebufenozide residues. No tebufenozide was detected (LOD, 0.02 ug/g) in soil samples collected from 2.5 - 5.0 cm depth during zero to 85 days post-spray irrespective of the dosage rate. Samples from the plot sprayed at the highest dosage rate contained 0.05 ug/g on the 107th and 408th day post spray. All the other samples (2.5 - 5.0 cm cores) including the ones from 5.0 - 10 and 10 - 15 cm had no detectable amounts of tebufenozide except for the occasional incidence of "trace" amounts. The lack of downward mobility observed in the study could be due to strong adsorption of the tebufenozide onto the sandy soil(3).

The Henry's Law constant for tebufenozide is estimated as 1.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-8 mm Hg(1), and water solubility, 0.83 mg/l(1). This Henry's Law constant indicates that tebufenozide is expected to be essentially nonvolatile from water surfaces(2).|Volatilization of tebufenozide from soil surfaces may occur based on results from a laboratory microcosm study; 200 g aliquots of sandy litter, sandy soil, clay litter, and clay soil each containing tebufenozide at a concn of 10 mg/kg were analyzed. The post volatilization residues (mg/kg) in samples kept in darkness at 30 °C for 10 days were 8.89 for sandy litter, 8.29 for sandy soil, 9.02 for clay litter, and 8.45 for clay soil(1).

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

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

The absorption, distribution, excretion and metabolism of tebufenozide in rats was investigated. Tebufenozide is partially absorbed, is rapidly excreted and does not accumulate in tissues. Although tebufenozide is mainly excreted unchanged, a number of polar metabolites were identified.

In the rat, 16 whole-molecule metabolites are formed as a result of oxidation of the alkyl substituents of the aromatic rings, primarily at the benzylic positions.|In apples, grapes, rice, & sugar beet, the major component is unchanged tebufenozide. Metabolites which are detected in small amounts result from oxidation of the alkyl substituents of the aromatic ring, primarily at the benzylic position.|Although tebufenozide is mainly excreted unchanged, a number of polar metabolites were identified. These metabolites are products of oxidation of the benzylic ethyl or methyl side chains of the molecule. These metabolites were detected in plant and other animal (rat, goat, hen) metabolism studies. Common metabolic pathways for tebufenozide have been identified in both plants (grape, apple, rice and sugar beet) and animals (rat, goat, hen). The metabolic pathway common to both plants and animals involves oxidation of the alkyl substituents (ethyl and methyl groups) of the aromatic rings primarily at the benzylic positions. Extensive degradation and elimination of polar metabolites occurs in animals such that residues are unlikely to accumulate in humans or animals exposed to these residues through the diet.

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

N'-(t-butyl)-N'-(3,5-dimethylbenzoyl)-N-(4-ethylbenzoyl)hydrazine

USEPA/OPP Pesticide Code 129026; Trade Names: RH-5992 2F, RH-5992 Technical.|Wettable powder, suspension concentrate, ultra-low volume suspension, dispersible powder, granule|Mimic (Rohm & Haas)|Confirm 2F (23% Tebufenozide)|For more Formulations/Preparations (Complete) data for TEBUFENOZIDE (7 total), please visit the HSDB record page.

Mode of action: Ecdysone agonist which acts by binding to the ecdysone receptor protein. The molting process is lethally accelerated.

Pesticide or Metabolite (M) Common Name: Tebufenozide; Commodity: Apples; Method Source: Rohm & Haas; Method ID: TR 34-94-38; Method Date: 3/22/94; Instrument: HPLC/UV; Estimated LOQ (ppm): 0.1. /From table/|Pesticide or Metabolite (M) Common Name: Tebufenozide; Commodity: Eggs, Liver; Method Source: Rohm & Haas; Method ID: TR 34-96-109; Method Date: 8/7/96; Instrument: HPLC; Estimated LOQ (ppm): 0.02. /From table/|Pesticide or Metabolite (M) Common Name: Tebufenozide; Commodity: Milk; Method Source: Rohm & Haas; Method ID: TR 34-96-109; Method Date: 8/7/96; Instrument: HPLC; Estimated LOQ (ppm): 0.01. /From table/

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

Tebufenozide has known environmental transformation products that include RH-2651, RH-2703, and RH-6595.