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Methoxyfenozide

HCID 105010
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Grundinformationen

CAS
161050-58-4
Standard-SMILES
COc1cccc(C(=O)NN(C(=O)c2cc(C)cc(C)c2)C(C)(C)C)c1C
InChIKey
QCAWEPFNJXQPAN-UHFFFAOYSA-N
Summenformel
C22H28N2O3
Durchschnittliche Molmasse
368,5 g/mol
Monoisotopische Masse
368,20999276

Überblick

Methoxyfenozide is a carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by 3-methoxy-2-methylbenzoyl, 3,5-dimethylbenzoyl, and tert-butyl groups respectively. It has a role as an insecticide, a xenobiotic and an environmental contaminant. It is a monomethoxybenzene and a carbohydrazide. It is functionally related to a N'-benzoyl-N-(tert-butyl)benzohydrazide.

Namen und Bezeichner

Bevorzugter Name
Methoxyfenozide
IUPAC
N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide
Englischer Name
Methoxyfenozide
Summenformel
C22H28N2O3
Molmasse
368.47

Namen und Synonyme

Methoxyfenozide161050-58-4IntrepidN'-tert-Butyl-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazideRunner3-Methoxy-2-methylbenzoic acid 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazideBenzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazideRH-2485DTXSID3032628N'-(tert-butyl)-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazideN-tert-butyl-N'-(3-methoxy-o-toluoyl)-3,5-xylohydrazide62A22651ZX
Weitere Namen anzeigen
MethoxyfenozidProdigy 240SC20%Methoxy SCethoxyfenozideResorcinol-13C3CAS:161050-58-4Methoxyphenozide
DTXCID1012628CHEBI:38449RH-112485RefChem:157081N-tert-butyl-N'-(3-methoxy-2-methylbenzoyl)-3,5-dimethylbenzohydrazide605-245-2N'-(tert-Butyl )-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide163442-56-6

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,6
Polarare Oberfläche (TPSA)
58,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
27
Formalladung
0
Komplexität
518

Experimentelle und physikochemische Eigenschaften

Pesticides · 6 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Methoxyfenozide) -> USDA PDB

Pesticide

LogPlog Kow = 3.7 (shake flask)
Color/FormWhite powder
Solubility · 2 Einträge

In DMSO 11, cyclohexanone 9.9, acetone 9 (all in g/100g at 20 °C)

In water, 3.3 mg/L at 20 °C

Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/.
Melting Point · 2 Einträge

206.2 - 208 °C

MP: 204 - 20.6 °C /Technical/

Collision Cross Section201.9 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3032628]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H400 (69.9%): 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 103 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Commission Regulation No 844/2012

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

05/3/EC, Reg. (EU) 2017/841, Reg. (EU) 2018/917, Reg. (EU) 2019/158, Reg. (EU) No 540/2011

REACH registered substance: Methoxyfenozide (EC: 605-245-2)

Methoxyfenozide: 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 · 5 Einträge

Tolerances are established for residues of the insecticide methoxyfenozide per se; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide in or on the following food commodities: [Table#7783]

Reregistration Eligibility Decision (RED) Scheduled for 2013

For combined residues of the insecticide methoxyfenozide; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide and its glucuronide metabolite RH-141,518; beta-D-Glucopyranuronic acid, 3-[2-(1,1-dimethylethyl)-2-(3,5-dimethylbenzoyl)-hydrazino]carbonyl-2-methylphenyl-] in the following commodities: [Table#7784]

Time-limited tolerances specified in the following table are established for residues of the insecticide methoxyfenozide per se (benzoic acid, 3-methoxy-2-methyl-,2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide), in or on the specified agricultural commodities, resulting from use of the pesticide pursuant to FFIFRA section 18 emergency exemptions. The tolerances expire and will be revoked on the date specified in the table. [Table#7785]

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 5 Einträge

Forty two groups of Sprague Dawley rats (up to 5/sex/group) were dosed by oral gavage with either (14)C-t-butyl-, (14)C-A-Ring-, or (14)C-B-Ring-Methoxyfenozide at doses of 10 or 1000 mg/kg. ... (14)C- Methoxyfenozide was extensively metabolized into 32 metabolites (26 identified) isolated from urine and feces, and 24 metabolites were found and characterized from the bile. Seven metabolites comprised of 59-69% and 42-56% of the dose at 10 and 1000 mg/kg dose levels, respectively. Parent comprised of 14-26% and 30-39% of the administered (14)C at 10 and 1000 mg/kg dose levels, respectively.

Parent compound was found only in the feces (not in the urine or bile) and comprised 14-26% and 30-39% of the administered dose for animals at the lower and higher doses, respectively, indicating that animals at the lower dose metabolized a greater fraction of the administered dose compared with animals at the higher dose. Seven metabolites (M10, M14, M16, M22, M24, M28, M30) were found to be present in feces plus urine each at >2% of the administered dose. The predominant metabolites were M14 (desmethylated parent) and M24 (hydroxy methyl derivative). Parent compound plus these seven metabolites accounted for 74-90% of the administered dose (in feces plus urine) in all groups. For each of these groups, the total of parent plus identified metabolites accounted for >/= 83% of the administered dose, i.e. the metabolic profile of methoxyfenozide in feces and urine was well defined. Less than 5% of the administered dose was present as metabolites formed from the cleavage of the amide bridge.

Two metabolites, M16 (A-ring glucuronide of M14) and M26 (A-ring glucuronide of M24), were the main metabolites in bile. M16 was present at 13% and 18% in males and females respectively, M26 was present at 5% in males and 11% in females, all other metabolites represented <3% of the administered dose. The presence of M16 and M26 at higher concentrations in bile than in feces indicates that these two metabolites were subject to subsequent hydrolysis.

The primary /metabolic/ pathway probably involves demethylation of the A-ring methoxy moiety to form the corresponding phenol (M14), which is conjugated with glucuronic acid to form M16. Hydroxylation on the B-ring methyl moieties is also a significant metabolic pathway. Cleavage of methoxyfenozide to release either of the rings or the t-butyl group is only a minor pathway; none of the cleaved metabolites (M06, M07, M13, M32-36) were present at >2% of the dose. In males, however, cleaved metabolites represented up to about 50% of the metabolites found in urine. There was an indication that males cleaved more of the absorbed dose than did females, on the basis of urinary metabolite patterns.

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 212686
HRID 212686als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 260807
HRID 260807als Produktuspto-grants-1996_06
Reaktionsgleichung von HRID 260809
HRID 260809als Produktuspto-grants-1996_06
Reaktionsgleichung von HRID 1227845
HRID 1227845als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
Reaktionsgleichung von HRID 2225934
HRID 2225934als Produktuspto-grants-1994_09
Reaktionsgleichung von HRID 2225936
HRID 2225936als Produktuspto-grants-1994_09

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Datenbank-Bezeichner

CAS
161050-58-4、211236-73-6
PubChem CID
105010
DTXSID
DTXSID3032628
ChEMBL
CHEMBL55772
ChEBI
CHEBI:38449
UNII
62A22651ZX
EC Number
605-245-2
Nikkaji
J981.614C

Physikochemische Eigenschaften

Schmelzpunkt
204 · 204-205°
Dichte
1.098 · 1.098±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
Löslichkeit
25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:6): 0.1 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
pka
10.43 · 10.43±0.46(Predicted)
Aggregatzustand
Solid
Farbe
White to off-white
Henry's Law Constant
2.6 · 2.6×106 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
agricultureenvironmental
InChI
1S/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25)
InChIKey
QCAWEPFNJXQPAN-UHFFFAOYSA-N
SMILES
COc1cccc(C(=O)NN(C(=O)c2cc(C)cc(C)c2)C(C)(C)C)c1C
LogP
3.7 · 3.700
EPA chemische Informationen
Methoxyfenozide (161050-58-4)

For more FIFRA Requirements (Complete) data for Methoxyfenozide (7 total), please visit the HSDB record page.

Toxic Combustion ProductsCombustion generates toxic fumes of the following: nitrogen oxides. /Intrepid 2F Insecticide/
Hazard Classes and Categories · 2 Einträge

Aquatic Acute 1 (69.9%)

Hazardous to the aquatic environment (Acute) - Category 2

Sicherheit und Schutzausrüstung

Firefighting HazardsPesticide particulates can become airborne. Dried product can burn. /Intrepid 2F Insecticide/
Fire Fighting Procedures · 3 Einträge

Remain upwind. Avoid breathing smoke. Use water spray to cool containers exposed to fire. Contain run-off. /Intrepid 2F Insecticide/

Wear positive-pressure, self-contained breathing apparatus and full protective clothing. Do not allow water from fire-fighting to enter water supplies. /Intrepid 2F Insecticide/

Use the following extinguishing media when fighting fires involving this material: carbon dioxide, dry chemical, water spray or foam. /Intrepid 2F Insecticide/

Storage Conditions · 2 Einträge

Do not store this material near food, feed or drinking water. The minimum recommended storage temperature for this material is 32 °F (0 °C). The maximum recommended storage temperature for this material is 104 °F (40 °C). Store in a well-ventilated area. Keep container tightly closed when not in use. /Intrepid 2F Insecticide/

Store in a cool dry well-ventilated area, but not below 32 °F. /Intrepid 2F Insecticide/

Cleanup Methods · 2 Einträge

Contain and absorb small spills with inert materials with sand or earth. Transfer liquids and solid diking material to separate suitable containers for recovery or disposal. Avoid breathing vapor. Keep spills and cleaning run-off out of municipal sewers and open bodies of water. ... . If exposed to material during clean-up operations, remove all contaminated clothing promptly. Wash all exposed skin areas with soap and water immediately after exposure. Thoroughly lauder clothing before reuse. Do not take clothing home to be laundered. /Intrepid 2F Insecticide/

Do not contaminate water when cleaning equipment or disposing of equipment washwaters. /Intrepid 2F Insecticide/

Disposal Methods · 3 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Wastes resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. /Intrepid 2F 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.

Preventive Measures · 5 Einträge

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Intrepid 2F Insecticide/

For terrestrial uses, do not apply directly to water or to areas where surface water is present or to intertidal areas below the mean high water mark. /Intrepid 2F Insecticide/

Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove contaminated clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Intrepid 2F Insecticide/

Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If not such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Intrepid 2F Insecticide/

For more Preventive Measures (Complete) data for Methoxyfenozide (7 total), please visit the HSDB record page.

Allowable Tolerances · 5 Einträge

Tolerances are established for residues of the insecticide methoxyfenozide per se; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide in or on the following food commodities: [Table#7777]

For combined residues of the insecticide methoxyfenozide; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide and its glucuronide metabolite RH-141,518; beta-D-Glucopyranuronic acid, 3-[2-(1,1-dimethylethyl)-2-(3,5-dimethylbenzoyl)-hydrazino]carbonyl-2-methylphenyl-] in the following commodities: [Table#7778]

Time-limited tolerances specified in the following table are established for residues of the insecticide methoxyfenozide per se (benzoic acid, 3-methoxy-2-methyl-,2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide), in or on the specified agricultural commodities, resulting from use of the pesticide pursuant to FFIFRA section 18 emergency exemptions. The tolerances expire and will be revoked on the date specified in the table. [Table#7779]

Tolerances with regional registrations. Tolerances are established for residues of the insecticide methoxyfenozide, including its metabolites and degradates. Compliance with the tolerance levels specified in this paragraph is to be determined by measuring only methoxyfenozide, benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide. [Table#7780]

For more Allowable Tolerances (Complete) data for Methoxyfenozide (6 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 2 Einträge

Applicators and other handlers must wear: Long-sleeved shirt and long pants. Chemical-resistant gloves made of any waterproof material. Shoes plus socks. /Intrepid 2F Insecticide/

... Restricted-entry interval (REI) of 4 hours. Personal protective equipment (PPE) required 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 is: Coveralls, Chemical resistant gloves made of any waterproof material. Shoes plus socks. /Intrepid 2F Insecticide/

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50; Species: Anas platyrhynchos (Mallard Duck, age 10 days) diet >5870 ppm for 8 days

LC50; Species: Colinus virginianus (Northern Bobwhite Quail, age 10 days) diet >5870 ppm for 8 days

LD50; Species: Colinus virginianus (Northern Bobwhite Quail, age 10 days) oral via capsule >2250 mg/kg

EC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, static; Concentration: >3400 ug/L for 5 days; Effect: decreased population abundance /98% purity/

For more Ecotoxicity Values (Complete) data for Methoxyfenozide (10 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.7(2) and a regression-derived equation(3), indicates that methoxyfenozide is expected to have low mobility in soil(SRC). Volatilization of methoxyfenozide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Methoxyfenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.70(2) and a regression-derived equation(3), indicates that methoxyfenozide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 130(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Using natural lake water, an aqueous photolysis half-life range of 7 to 10 days has been reported(7). Biodegradation data in water were not available(SRC, 2011).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methoxyfenozide, which has an estimated vapor pressure of 3.5X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase methoxyfenozide may be removed from the air by wet or dry deposition(SRC). Methoxyfenozide contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 Eintrag

The Koc of methoxyfenozide is estimated as 1100(SRC), using a log Kow of 3.70(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methoxyfenozide is expected to have low mobility in soil.

Artificial Pollution SourcesMethoxyfenozide's production may result in its release to the environment through various waste streams; its use as an insecticide(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 Eintrag

An estimated BCF of 130 was calculated in fish for methoxyfenozide(SRC), using a log Kow of 3.70(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 Eintrag

The Henry's Law constant for methoxyfenozide is estimated as 3.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methoxyfenozide is expected to be essentially nonvolatile from water and moist soil surfaces(2). Methoxyfenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-11 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Acute Exposure/ Methoxyfenozide was not irritating to rabbit skin and produced only minimal, transient irritation to rabbit eyes. Negative results were obtained in a Magnusson and Kligman maximization test for skin sensitization in guinea-pigs.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In an initial study, groups of five male and five female Crl: CD BR rats were given diets containing methoxyfenozide (purity, 90%) at concentrations of up to 20,000 mg/kg for 2 weeks. All rats were observed routinely for signs of ill health or reaction to treatment, body weight and feed consumption. After 2 weeks of treatment, blood samples were collected for measurement of hematology (including reticulocytes, but not methemoglobin formation) and clinical chemistry parameters. Histological examination was limited to seven major organs at the highest dose and controls, except for the liver, thyroid and pituitary where there was evidence of substance-related effects at the highest dose. There were no deaths and no effects on clinical signs, body weight or feed consumption were evident. No treatment-related adverse hematological effects were observed in either sex at any dose. No clear treatment-related clinical chemistry changes were seen in males at doses of up to 5,000 mg/kg or in females at doses of up to 20,000 mg/kg. A treatment-related decrease (by 47%, statistically significant) in triglyceride concentrations was observed in males at 20,000 mg/kg. Increases in absolute and relative weights of liver (14-23%) and adrenals (up to 30%) were noted at >5000 mg/kg. Minimal to slight hepatocyte hypertrophy was observed in all rats at 20,000 mg/kg and in three females at 5,000 mg/kg. There was evidence of single cell necrosis in the livers of animals receiving 20,000 mg/kg. A dose-related minimal to slight hypertrophy and/or hyperplasia of the follicular cells of the thyroid occurred in male and female rats at >/= 1,000 mg/kg. Minimal hypertrophy of the zona fasciculata of the adrenal cortex was seen in three females at 20,000 mg/kg. Isolated findings of adrenal hypertrophy in females at 1,000 and 5,000 mg/kg were of questionable significance. The NOAEL was 250 mg/kg (equal to 24 mg/kg per day) on the basis of follicular cell hypertrophy and/or hyperplasia of the thyroid in both sexes at 1000 mg/kg (equal to 98 mg/kg bw per day).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In an initial study, groups of five female Crl:CD-1(ICR)BR mice were given diets containing methoxyfenozide (purity, 99.2%) at a concentration of 0, 50, 250, 1000, 2500 or 7000 mg/kg for 2 weeks. Limited investigations of clinical chemistry and hematology were performed in addition to routine investigations of mortality, clinical signs, body weight and food consumption. Microscopic examination was performed on the thyroid, liver, spleen, adrenals, kidney and pituitary from animals in the control group and the group receiving the highest dose. In addition, the liver from each mouse in all other treatment groups was also examined microscopically. No clinical signs of ill health or reaction to treatment after 2 weeks of dietary exposure to methoxyfenozide were recorded. No treatment-related effects on hematology, clinical chemistry, body weight or food consumption were observed. The only findings of note were a statistically significant increase in relative liver weights at 7000 mg/kg and periportal hepatocyte hyperplasia at >/= 2500 mg/kg. The no-observed-adverse-effect level (NOAEL) was 1000 mg/kg (equal to 217 mg/kg per day) on the basis of histopathological changes in the liver at 2500 mg/kg.

Environmental Abiotic Degradation · 1 Eintrag

Methoxyfenozide is stable to hydrolysis at pH 5, 7 and 9(1) and has been reported as relatively not important in the environment when compared to photolysis(2). Methoxyfenozide contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC). A photolytic half-life in pond water of 77 days has been reported(1). Photodecomposition in aqueous solutions (sterilized lake water from Guishui Lake, south of Beijing China) follows first-order kinetics under UV and natural sunlight. This slightly eutrophic lake is influenced by agricultural runoff(2). Half-lives of 10.85 minutes and 6.63-10.16 days, under UV (detection performed at 230 nm) and natural sunlight conditions (sunlight intensity at 300 to 400 nm), respectively, have been reported(2). Under UV degradation, two products were identified: N-t-butyl-N-(3,5-dimethylbenzoyl) and 3,7-dimethyl-benzoatedihydrofuran(2). A soil photolysis half-life has been reported as 173 days(1).

Probable Routes of Human ExposureOccupational exposure to methoxyfenozide may occur through inhalation and dermal contact with this compound at workplaces where methoxyfenozide is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 Eintrag

Methoxyfenozide's production may result in its release to the environment through various waste streams; its use as an insecticide will result in its direct release to the environment. If released to air, an estimated vapor pressure of 3.5X10-11 mm Hg at 25 °C indicates methoxyfenozide will exist solely in the particulate phase in the atmosphere. Particulate-phase methoxyfenozide will be removed from the atmosphere by wet or dry deposition. Methoxyfenozide contains chromophores that absorb at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight. If released to soil, methoxyfenozide is expected to have low mobility based upon an estimated Koc of 1,100. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 3.8X10-12 atm-cu m/mole. Methoxyfenozide may not volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, methoxyfenozide is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 130 suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism. Methoxyfenozide is stable to hydrolysis at environmental pH. Using natural lake water, an aqueous photolysis half-life range of 7 to 10 days has been reported. Occupational exposure to methoxyfenozide may occur through inhalation and dermal contact with this compound at workplaces where methoxyfenozide is produced or used. (SRC)

Antidote and Emergency Treatment · 3 Einträge

/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/

Regulatorische Informationen

FIFRA Requirements · 5 Einträge

Tolerances are established for residues of the insecticide methoxyfenozide per se; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide in or on the following food commodities: [Table#7783]

Reregistration Eligibility Decision (RED) Scheduled for 2013

For combined residues of the insecticide methoxyfenozide; benzoic acid, 3-methoxy-2-methyl-, 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide and its glucuronide metabolite RH-141,518; beta-D-Glucopyranuronic acid, 3-[2-(1,1-dimethylethyl)-2-(3,5-dimethylbenzoyl)-hydrazino]carbonyl-2-methylphenyl-] in the following commodities: [Table#7784]

Time-limited tolerances specified in the following table are established for residues of the insecticide methoxyfenozide per se (benzoic acid, 3-methoxy-2-methyl-,2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazide), in or on the specified agricultural commodities, resulting from use of the pesticide pursuant to FFIFRA section 18 emergency exemptions. The tolerances expire and will be revoked on the date specified in the table. [Table#7785]

For more FIFRA Requirements (Complete) data for Methoxyfenozide (7 total), please visit the HSDB record page.

Sicherheitsdaten

wgk
2
ridadr
UN 3077 9 / PGIII
hs_code
29145090
risk_code
51/53
Toxizität
LD50 in rats, mice (mg/kg): >5000, >5000 orally; in rats (mg/kg): >2000 dermally; LC50 in rats (mg/l): >4.3 by inhalation; LC50 (8 day dietary) in mallard duck, bobwhite quail (mg/kg diet): >5620, >5620; LC50 in bluegill sunfish, Daphnia magna (mg/l): >4.3 (96 hr); 3.7 (48 hr) (Le)
hazard_code
N
safety_code
60
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
161050-58-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 DermalAquatic Chronic 2

Results for the animals receiving diets containing methoxyfenozide for 14 days plus a single dose of (14C) methoxyfenozide at 10 mg/kg bw by gavage showed evidence of induction of metabolism. Concentrations of M22, M28 and M30 increased, while concentrations of M14 and M24 were reduced relative to concentrations in animals that received only a single dose of (14C) methoxyfenozide at 10 mg/kg bw.

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 · 4 Einträge

Forty two groups of Sprague Dawley rats (up to 5/sex/group) were dosed by oral gavage with either (14)C-t-butyl-, (14)C-A-Ring-, or (14)C-B-Ring-Methoxyfenozide at doses of 10 or 1000 mg/kg. Some treatments were performed by combining appropriate amount of non-labeled or (13)C-labeled Methoxyfenozide to the (14)C-Methoxyfenozide. Three types of experiments were performed: (1) determination of excretion, distribution, and mass balance 120 hours post dose; (2) pharmacokinetics in blood (Cmax and 1/2 Cmax); and (3) tissue distribution of (14)C at Cmax and 1/2 Cmax. The (14)C was mostly excreted during the first 24 hours with 58-77% of the administered dose recovered in the feces and 4-9% of the dose found in urine from day 0-1. The position of the carbon label did not alter the excretion profile significantly. Approximately, 0.07-0.23% of (14)C remained in the tissues, and 0.03-0.11% were recovered as (14)C-CO2 and volatile organics from day 0-5 post dose. The maximum concentrations of (14)C-Methoxyfenozide in the blood were observed at 15-30 minutes post dose for all three (14)C-labels. The highest tissue concentration of (14)C was in the liver. The (14)C residues were rapidly cleared from all organs in the rat. Based on the recovery of (14)C from the bile, urine, tissues and carcasses, 62-70% of the administered dose was systemically absorbed.

The tissue distribution of radioactivity was investigated after a single dose of A-ring-labelled or t-butyl-labelled methoxyfenozide administered by gavage (at Cmax, 1/2 Cmax and at 5 days after dosing at 10 or 1000 mg/kg bw), and after a single dose of B-ring-labelled methoxyfenozide (5 days after dosing at 10 mg/kg bw). Tissue distribution was also investigated after dosing with A-ring-labelled methoxyfenozide at 10 mg/kg bw as a pulse dose (5 days after dosing) and as a repeated dose (at 0.25 hr after the last dose, at about Cmax). Similar results were seen in all experiments. The absorbed radioactivity was widely distributed, with the highest concentration of absorbed radioactivity found in the liver at 0.5-2 hr after dosing (the higher concentrations found in the stomach and intestinal tract were attributed to largely unabsorbed material). ... Clearance from the body was extensive; 5 days after a single dose of 10 mg/kg bw, the highest percentage of radioactivity, representing <0.1% of the administered dose, was found in the liver.

The biliary excretion of radiolabel after a single oral dose of ((14)C-A-ring) methoxyfenozide at 10 mg/kg was investigated in bile-duct cannulated rats. Biliary excretion was rapid, with 22% (females) and 50% (males) of the administered dose being excreted within 12 hr. Overall, 38% (females) and 64% (males) of the radiolabel was excreted in bile within 72 hr. Considerable variability between individual animals was seen in cannulated female rats (bile, 13-55%; and urine, 5-43% within 72 hr), but the overall amount absorbed (in bile, urine, carcass and tissues) was similar for all four females (56-67%). Taking the biliary component into account, the overall extent of oral absorption of methoxyfenozide at a dose of 10 mg/kg bw was 60-70% in both sexes.

The dermal absorption in vivo of methoxyfenozide formulated as an aqueous flow-able liquid (RH-112,485 2F) or as a wettable powder (RH-112,485 280WP) was tested in rats in a study that was designed to comply with US EPA guidelines and GLP. The methoxyfenozide administered was uniformly labelled with (14)C on the methoxyphenyl ring; this is acceptable given the limited cleavage seen in studies of oral metabolism. To provide data on exposure to the concentrated product and in-use-dilutions, groups of four male Crl : CD BR rats received radiolabelled methoxyfenozide at three aqueous dilutions (0.025, 0.25, or 2.5% w/v), applied in a volume of 100 uL to a shaved area of about 10 sq cm for 1, 10, or 24 hr. Systemically absorbed methoxyfenozide was defined as the radiolabel found in the carcass, urine (plus urine funnel and cage washes), feces, and whole blood. For RH-112,485 2F, the total mean recovery of radiolabel in all groups ranged from 98% to 114%. After an exposure of 1, 10, or 24 hr to (14)C-labelled RH-112,485 2F formulation diluted in water to a concentration of 2.5, 0.25, or 0.025% w/v, a small amount of radiolabel (<1-4%) was systemically absorbed. For RH-112,485 280 WP, three animals with poor recoveries were excluded from further analysis. The total mean recovery of radiolabel in all groups ranged from 85% to 110%. After an exposure of 1, 10, or 24 hr to (14)C-labelled RH-112,485 280 WP at a concentration of 2.5, 0.25, or 0.025% w/v, <1-2% of radiolabel was systemically absorbed. Findings were similar for both formulations. The amount of radiolabel that was systemically absorbed did not increase linearly between the 10-hr and 24-hr exposure periods, indicating that most of the radiolabel that remained in or on the skin after washing was tightly bound and was not available for systemic absorption. This study shows that methoxyfenozide is poorly absorbed (<4%) after dermal exposure to either of the formulated products or in-use dilutions. The low rate of dermal absorption may be attributed to very low solubility in water (3.3 mg/L at 20 °C).

Verwendung und Herstellung

Uses · 3 Einträge

For methoxyfenozide (USEPA/OPP Pesticide Code: 121027) 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./

Insecticide

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

Formulations/Preparations · 5 Einträge

Suspension concentrate, wettable powder.

Methoxyfenozide Technical (Dow Agrosciences, LLC) Methoxyfenozide 98.2%

Intrepid 80WSP Agricultural Insecticide (Dow Agrosciences, LLC) Methoxyfenozide 80%

Intrepid 2F Agricultural Insecticide (Dow Agrosciences, LLC) Methoxyfenozide 22.6%

Intrepid Mup (Dow Agrosciences, LLC) Methoxyfenozide 80%

Use Classification · 2 Einträge

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies methoxyfenozide as unlikely to present an acute hazard in normal use; Main Use: insecticide.

Anwendungen

VerwendenInsecticide.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

tert-Butyl-hydrazinen-HexanN,N-Dimethylformamid3,5-Dimethoxybenzoylchlorid3-Methoxy-2-methylbenzoyl chloride2,6-Dichlortoluol3,5-Dimethylbenzoesure3-Methoxy-2-methylbenzoic acidThionyldichloridtert-Butylhydrazinmonohydrochlorid

Anbieter101 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by 3-methoxy-2-methylbenzoyl, 3,5-dimethylbenzoyl, and tert-butyl groups respectively.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Two beagle dogs/sex/group were treated in the diet with 0, 500, 5000, 15000 or 30000 ppm of Methoxyfenozide (RH-112,485 Technical, purity: 98%) for 2 weeks ((M): 0, 17.8, 202.2, 508.9 and 1002.5 mg/kg/day, (F): 0, 19.5, 196.4, 756.9 and 1185.8 mg/kg/day). No treatment-related clinical signs were evident. Mean red blood cell counts were reduced for the females at 15000 and 30000 ppm (66 and 73% of baseline values, respectively). The hemoglobin and hematocrit values were likewise reduced for these females. The mean platelet counts were increased the most for these same females. Methemoglobinemia was quite evident for these females with mean values of 3.4 and 3.3% for the 15000 and 30000 ppm groups, respectively in comparison with pretest values of 0.8%. The percentage of reticulocytes in the blood was increased in all groups including the control animals from that of the baseline values. However, the females in the two highest dose groups experienced the most severe response with values of 6.9 and 5.1%, respectively. Heinz bodies were noted in the blood of all four of these females. Histopathologic examination of the livers from these females revealed hemosiderin in the Kupffer cells and the phagocytic cells lining the hepatic sinusoids. This observation was indicative of an increased rate of removal of red blood cells from circulation.

For more Non-Human Toxicity Excerpts (Complete) data for Methoxyfenozide (21 total), please visit the HSDB record page.