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테부페노지드

Tebufenozide

HCID 91773
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
112410-23-8
표준 SMILES
CCc1ccc(C(=O)NN(C(=O)c2cc(C)cc(C)c2)C(C)(C)C)cc1
InChIKey
QYPNKSZPJQQLRK-UHFFFAOYSA-N
분자식
C22H28N2O2
평균 분자량
352.5 g/mol
단동위원소 질량
352.21507814

개요

Tebufenozide is a carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by tert-butyl, 3,5-dimethylbenzoyl and 4-ethylbenzoyl groups respectively. It is an insecticide used widely against caterpillars. It has a role as a xenobiotic, an ecdysone agonist and an environmental contaminant. It is functionally related to a N'-benzoyl-N-(tert-butyl)benzohydrazide.

이름 및 식별자

우선 이름
Tebufenozide
IUPAC
N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide
현지명
테부페노지드
영어명
Tebufenozide
분자식
C22H28N2O2
분자량
352.47

이름 및 동의어

Tebufenozide112410-23-8N-tert-Butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazideConfirmRH-5992MimicDTXSID4034948TNN5MI5EKFN'-(t-Butyl)-N'-(3,5-dimethylbenzoyl)-N-(4-ethylbenzoyl)hydrazine3,5-Dimethylbenzoic acid 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazideCHEBI:38452DTXCID2014948
이름 더 보기
테부페노자이드테부페노지드RoMdanConformConfirm(TM)MiMic 240LVMiMic 700WPebufenozide
RH5992RefChem:187654412-850-3601-185-6Tebufenozide [ISO]Tebufenozide-d9MFCD00467963Benzoic acid, 3,5-dimethyl-, 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide

데이터베이스 식별자

CAS
112410-23-8、142583-69-5
PubChem CID
91773
DTXSID
DTXSID4034948
ChEMBL
CHEMBL226968

물성

구조 계산 물성

XLogP
3.9
극성 표면적
49.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
4
무거운 원자 수
26
형식 전하
0
복잡도
479

실험 및 물리화학적 성질

Pesticides · 6건

Insecticides

Active substance -> EU Pesticides database: Approved

Pesticides -> Other Insecticides

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Tebufenozide) -> USDA PDB

LogP · 2건

log Kow= 4.25 (pH 7)

4.25

Density1.03 (20 °C, pycrometer method)
Color/FormOff-white powder
Solubility · 2건

Slightly soluble in organic solvents

In water, 0.83 mg/l @ 25 °C

DecompositionDT50 in natural pond water, in light, 30 days (25 °C).
Melting Point191 °C
Vapor Pressure · 2건

0.00000002 [mmHg]

2.25X10-8 mm Hg @ 25 °C

Physical DescriptionOff-white solid; [HSDB] Off-white powder; [MSDSonline]
Stability/Shelf LifeStable at 94 °C for 7 days. Stable to light in pH 7 aq soln, (25 °C). Stable in dark, sterile water 30 days, (25 °C). DT50 in natural pond water, in light, 30 days (25 °C).

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Warning

H400 (31.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 89 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 5건

Regulation (EC) No 396/2005 (amended)

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

2011/60/EU, Reg. (EU) 2018/1266, Reg. (EU) 2020/2007, Reg. (EU) 2024/1206, Reg. (EU) No 540/2011

REACH registered substance: N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide (EC: 412-850-3)

Tebufenozide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

FIFRA Requirements · 5건

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 129026; Tpye of Pesticide: conventional-insecticide; Use Site: food use/walnuts; Year: 1995.

Tolerances are established for residues of the insecticide tebufenozide, benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, in or on the following raw agricultural commodities: almond, hulls; apple, pomace; apple; berry (crop group 13); canola, refined oil; canola, seed; cotton; cotton, gin byproducts; cranberry; fruiting vegetables (except cucurbits); head and stem Brassica crop subgroup; kiwifruit; leafy Brassica green crop subgroup; leafy greens crop subgroup; leafy petioles crop subgroup; peppermint, tops; pome fruit; spearmint, tops; tree nut crop group including pistachios; turnip, roots; turnip, tops; walnut.

화학 및 산업

약리 정보

Metabolism/Metabolites · 3건

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.

MeSH Pharmacological ClassificationPesticides 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.
Absorption, Distribution and Excretion · 1건

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.

용도 및 제조

Uses · 5건

Used as insecticide for control of lepidopteron larvae on rice, fruit, row crops, nut crops, vegetables, vines, and forestry; [HSBD]

Farming (Pesticides) [Category: Industry]

관련 반응

0건
반응 기록 만들기

현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
ChEBI
CHEBI:38452
UNII
TNN5MI5EKF
EC Number
412-850-3、601-185-6
Nikkaji
J540.289A
Ionization Efficiency · 6건

Positive

2.27

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 2건

193.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID4034948]

202.78 Ų [M+Na]+

물리화학적 성질

녹는점
191 °; · 191°; mp 186-188° (Sundaram, 1081)
밀도
1.074 · 1.074±0.06 g/cm3(Predicted)
증기압
3 x · 3 x 10 -6 Pa (25 °C)
저장 조건
0 · 0-6°C
용해도
Chloroform: Slightly Soluble,Methanol: Slightly Soluble
산도 계수 (pKa)
10.89 · 10.89±0.46(Predicted)
수용성
0.83 mg · 0.83mg l-1(20°C)
물리적 상태
Solid
색상
White to off-white
BRN
7822297 · 7822297
Henry's Law Constant
7.6 · 7.6×102 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
InChI=1S/C22H28N2O2/c1-7-17-8-10-18(11-9-17)20(25)23-24(22(4,5)6)21(26)19-13-15(2)12-16(3)14-19/h8-14H,7H2,1-6H3,(H,23,25)
InChIKey
QYPNKSZPJQQLRK-UHFFFAOYSA-N
SMILES
C(N(C(C)(C)C)NC(=O)C1=CC=C(CC)C=C1)(=O)C1=CC(C)=CC(C)=C1
LogP
4.24 · 4.240 (est)
EPA
Tebufenozide (112410-23-8)

Tolerances are established for the combined residues of tebufenozide and its metabolites benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-((4-carboxymethyl)benzoyl)hydrazide), benzoic acid, 3-hydroxymethyl,5-methyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, the stearic acid conjugate of benzoic acid, 3-hydroxymethyl-5-methyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydr azide /in or on the following raw agricultural commodities/: fat of cattle, goats, hogs, horses, and sheep; meat of cattle, goats, hogs, horses, and sheep; meat byproducts of cattle, goats, hogs, horses, and sheep; milk.

Time-limited tolerances are established for residues of the insecticide benzoic acid in connection with use of the pesticide /tebufenozide/ under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specificed: beet, garden, roots; beet, garden, tops; egg; grape; grass, forage; grass, hay; longan; lychee; peanut; peanut, hay; peanut, meal; peanut, refined oil; poultry, fat; poultry, meat; poultry meat byproducts; sunflower, seed; sweet potato, roots; vegetable, foliage of legume, group; vegetable, legume, group.

Tolerances are established for the indirect or inadvertent combined residues of tebufenozide benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide and its metabolite benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydrazide in or on the raw agricultural commodities when present therein as a result of the application of tebufenozide to growing crops listed ... as follows: foliage of legume vegetables; forage, fodder, hay and straw of cereal grains; forage, fodder, straw and hay of non-grass animal feeds; grass forage, fodder and hay.

Hazard Classes and Categories · 6건

Aquatic Chronic 2 (100%)

Aquatic Acute 1 (31.5%)

Hazardous to the aquatic environment (chronic) - category 2

Specific target organ toxicity - Repeated exposure - Category 2 (blood system, liver)

Reproductive toxicity - Category 2

Aquatic Chronic 2

State Drinking Water Guidelines(ME) MAINE 140 ug/L

안전 및 보호

Disposal Methods · 1건

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.

Allowable Tolerances · 4건

Tolerances are established for residues of the insecticide tebufenozide, benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, in or on the following raw agricultural commodities: almond, hulls: 25 ppm; apple, pomace: 3.0 ppm; apple: 1.0 ppm; berry (crop group 13): 3.0 ppm; canola, refined oil: 4.0 ppm; canola, seed: 2.0 ppm; cotton: 1.5 ppm; cotton, gin byproducts: 30 ppm; cranberry: 1.0 ppm; fruiting vegetables (except cucurbits): 1.0 ppm; head and stem Brassica crop subgroup: 5.0 ppm; kiwifruit: 0.5 ppm; leafy Brassica green crop subgroup: 10.0 ppm: leafy greens crop subgroup: 10.0 ppm; leafy petioles crop subgroup: 2.0 ppm; peppermint, tops: 10.0 ppm; pome fruit: 1.5 ppm; spearmint, tops: 10.0 ppm; tree nut crop group including pistachios: 0.1 ppm; turnip, roots: 0.3 ppm; turnip, tops: 9.0 ppm; walnut: 0.1 ppm.

Tolerances are established for the combined residues of tebufenozide and its metabolites benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-((4-carboxymethyl)benzoyl)hydrazide), benzoic acid, 3-hydroxymethyl,5-methyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, the stearic acid conjugate of benzoic acid, 3-hydroxymethyl-5-methyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydr azide /in or on the following raw agricultural commodities/: fat of cattle, goats, hogs, horses, and sheep: 0.1 ppm; meat of cattle, goats, hogs, horses, and sheep: 0.08 ppm; meat byproducts of cattle, goats, hogs, horses, and sheep: 0.08 ppm; milk: 0.04 ppm.

Time-limited tolerances are established for residues of the insecticide benzoic acid in connection with use of the pesticide /tebufenozide/ under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specificed: beet, garden, roots: 0.3 ppm (12/31/02); beet, garden, tops: 9.0 ppm (12/31/02); egg: 0.01 ppm (06/30/03); grape: 3.0 ppm (12/31/03); grass, forage: 5.0 ppm (06/30/03); grass, hay: 18.0 ppm (06/30/03); longan: 1.0 ppm (12/31/03); lychee: 1.0 ppm (12/31/03); peanut: 0.05 ppm (06/30/03); peanut, hay: 5.0 ppm (06/30/03); peanut, meal: 0.15 ppm (06/30/03); peanut, refined oil: 0.15 ppm (06/30/03); poultry, fat: 0.1 ppm (06/30/03); poultry, meat: 0.01 ppm (06/30/03); poultry meat byproducts: 0.05 ppm (06/30/03); sunflower, seed: 1.5 ppm (12/31/02); sweet potato, roots: 0.25 ppm (12/31/02); vegetable, foliage of legume, group: 7.0 ppm (12/31/02); vegetable, legume, group: 2.0 ppm (12/31/02).

Tolerances are established for the indirect or inadvertent combined residues of tebufenozide benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide and its metabolite benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydrazide in or on the raw agricultural commodities when present therein as a result of the application of tebufenozide to growing crops listed ... as follows: foliage of legume vegetables: 0.1 ppm (expiration/revocation date 9/30/03); forage, fodder, hay and straw of cereal grains: 0.5 ppm (expiration/revocation date 9/30/03); forage, fodder, straw and hay of non-grass animal feeds: 0.5 ppm (expiration/revocation date 9/30/03); grass forage, fodder and hay: 0.5 ppm (expiration/revocation date 9/30/03).

독성 정보

Ecotoxicity Values · 5건

LD50 Quail oral >2150 mg/kg

LC50 Mallard ducks & quail >5000 mg/kg (8 day dietary)

LC50 Rainbow trout 5.7 mg/l (96 hr) /Conditions of bioassay not specified/.

LC50 Bluegill sunfish 3.0 mg/l (96 hr) /Conditions of bioassay not specified/.

For more Ecotoxicity Values (Complete) data for TEBUFENOZIDE (7 total), please visit the HSDB record page.

Environmental Fate · 3건

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).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Ecotoxicity Excerpts · 2건

/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).

Soil Adsorption/Mobility · 1건

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).

Artificial Pollution SourcesTebufenozide'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).
Environmental Biodegradation · 2건

AEROBIC: Studies show that tebufenozide was stable in dark, sterilized stream water with a half-life of 734 days, but degraded more rapidly in dark, unsterilized stream water with half-life of 181 days. 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(1). Studies have also reported a metabolic DT50 of 100 days for aerobic, aquatic soil (3 soil types) at 25 °C(2).

ANAEROBIC: A metabolic half-life of 179 days was reported using an aquatic silt loam soil incubated at 25 °C(1).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1건

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).

Volatilization from Water/Soil · 2건

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).

Non-Human Toxicity Excerpts · 5건

/LABORATORY ANIMALS: Acute Exposure/ The toxicology profile of tebufenozide shows no evidence of physiological effects characteristic of the disruption of the hormone estrogen. Based on structure-activity information, tebufenozide is unlikely to exhibit estrogenic activity. Tebufenozide was not active in a direct in vitro estrogen binding assay. No indicators of estrogenic or other endocrine effects were observed in mammalian chronic studies or in mammalian and avian reproduction studies. Ecdysone has no known effects in vertebrates. Overall, the weight of evidence provides no indication that tebufenozide has endocrine activity in vertebrates.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The NOAEL in a 90-day rat feeding study was 200 ppm (13 mg/kg/day for males, 16 mg/kg/day for females). The LOAEL was 2,000 ppm (133 mg/kg/day for males, 155 mg/kg/day for females). Decreased body weights in males and females was observed at the LOAEL of 2,000 ppm. As part of this study, the potential for tebufenozide to produce subchronic neurotoxicity was investigated. Tebufenozide did not produce neurotoxic or neuropathologic effects when administered in the diets of rats for 3 months at concns up to and including the limit dose of 20,000 ppm (NOAEL=1,330 mg/kg/day for males, 1,650 mg/kg/day for females).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day feeding study with mice, the NOAEL was 20 ppm (3.4 and 4.0 mg/kg/day for males and females, respectively). The LOAEL was 200 ppm (35.3 and 44.7 mg/kg/day for males and females, respectively). Decreases in body weight gain were noted in male mice at the LOAEL of 200 ppm. A 90-day dog feeding study gave a NOAEL of 50 ppm (2.1 mg/kg/day for males and females). The LOAEL was 500 ppm (20.1 and 21.4 mg/kg/day for males and females, respectively). At the LOAEL, females exhibited a decr in rate of weight gain and males presented an increased reticulocyte.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A 10-wk study was conducted in the dog to examine the reversibility of the effects on hematological parameters that were observed in other dietary studies with the dog. Tebufenozide was administered for 6 weeks in the diet to 4 male dogs at concns of either 0 or 1,500 ppm. After the sixth wk, the dogs receiving treated feed were switched to the control diet for 4 weeks. Hematological parameters were measured in both groups prior to treatment, at the end of the 6-wk treatment, after 2 weeks of recovery on the control diet and after 4 weeks of recovery on the control diet. All hematological parameters in the treated/recovery group were returned to control levels indicating that the effects of tebufenozide on the hemopoietic system are reversible in the dog.

For more Non-Human Toxicity Excerpts (Complete) data for TEBUFENOZIDE (13 total), please visit the HSDB record page.

Evidence for CarcinogenicityCancer Classification: Group E Evidence of Non-carcinogenicity for Humans

규제 정보

FIFRA Requirements · 5건

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 129026; Tpye of Pesticide: conventional-insecticide; Use Site: food use/walnuts; Year: 1995.

Tolerances are established for residues of the insecticide tebufenozide, benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, in or on the following raw agricultural commodities: almond, hulls; apple, pomace; apple; berry (crop group 13); canola, refined oil; canola, seed; cotton; cotton, gin byproducts; cranberry; fruiting vegetables (except cucurbits); head and stem Brassica crop subgroup; kiwifruit; leafy Brassica green crop subgroup; leafy greens crop subgroup; leafy petioles crop subgroup; peppermint, tops; pome fruit; spearmint, tops; tree nut crop group including pistachios; turnip, roots; turnip, tops; walnut.

Tolerances are established for the combined residues of tebufenozide and its metabolites benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-((4-carboxymethyl)benzoyl)hydrazide), benzoic acid, 3-hydroxymethyl,5-methyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide, the stearic acid conjugate of benzoic acid, 3-hydroxymethyl-5-methyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydr azide /in or on the following raw agricultural commodities/: fat of cattle, goats, hogs, horses, and sheep; meat of cattle, goats, hogs, horses, and sheep; meat byproducts of cattle, goats, hogs, horses, and sheep; milk.

Time-limited tolerances are established for residues of the insecticide benzoic acid in connection with use of the pesticide /tebufenozide/ under section 18 emergency exemptions granted by EPA. The tolerances will expire and are revoked on the dates specificed: beet, garden, roots; beet, garden, tops; egg; grape; grass, forage; grass, hay; longan; lychee; peanut; peanut, hay; peanut, meal; peanut, refined oil; poultry, fat; poultry, meat; poultry meat byproducts; sunflower, seed; sweet potato, roots; vegetable, foliage of legume, group; vegetable, legume, group.

Tolerances are established for the indirect or inadvertent combined residues of tebufenozide benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide and its metabolite benzoic acid, 3,5-dimethyl-1-(1,1-dimethylethyl)-2-(4-(1-hydroxyethyl)benzoyl)hydrazide in or on the raw agricultural commodities when present therein as a result of the application of tebufenozide to growing crops listed ... as follows: foliage of legume vegetables; forage, fodder, hay and straw of cereal grains; forage, fodder, straw and hay of non-grass animal feeds; grass forage, fodder and hay.

State Drinking Water Guidelines(ME) MAINE 140 ug/L

안전 데이터

wgk
2
ridadr
UN 3077
독성
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)
HS 번호
29280000
risk_code
51/53
hazard_code
N
safety_code
61
포장분류
III
위험 등급
9
기존화학 물질
97-3-728
Hazard Classifications
Aquatic Chronic 2
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
112410-23-8(Hazardous Substances Data)

For Tebufenozide (USEPA/OPP Pesticide Code: 129026) 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./

Control of lepidopteran larvae on rice, fruit, row crops, nut crops, vegetables, vines, and forestry.

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

Methods of ManufacturingA.C. Hsu, H. E. Allen, AU 64289; eidem, US 4985461 (1986, 1991 both to Rohm & Haas)
Formulations/Preparations · 5건

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.

Use Classification · 2건

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

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

응용 분야

용도Tebufenozide is used to control lepidopterous larvae on rice, fruit, row crops, nut crops, vegetables and vines and in forestry.

상·하류 제품 정보

상류 원료

TERT-BUTYL-HYDRAZINE노르말헥산에틸벤젠염화알루미늄트라이클로로아세틸 염화물ChromatographyBenzoic acid, 3,5-diMethyl-, 1-(1,1-diMethylethyl)hydrazide3,5-Dimethylbenzoyl chloride4-Ethylbenzoyl chloride4-에틸벤조산3,5-디메틸벤조산tert-Butylhydrazine hydrochloride

추가 설명

정의ChEBI: A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by tert-butyl, 3,5-dimethylbenzoyl and 4-ethylbenzoyl groups respectively. It is an insecticide used widely against caterpillars.