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ヒドラメチルノン

Hydramethylnon

HCID 49901
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
67485-29-4
標準SMILES
CC1(C)CN=C(NN=C(C=Cc2ccc(C(F)(F)F)cc2)C=Cc2ccc(C(F)(F)F)cc2)NC1
InChIKey
IQVNEKKDSLOHHK-UHFFFAOYSA-N
分子式
C25H24F6N4
平均分子量
494.5 g/mol
単同位体質量
494.19051575

概要

Hydramethylnon appears as odorless yellow crystals. Insoluble in water. Used as an insecticide.

名称と識別子

優先名称
Hydramethylnon
IUPAC
N-[1,5-bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-ylideneamino]-5,5-dimethyl-4,6-dihydro-1H-pyrimidin-2-amine
現地名
ヒドラメチルノン
英語名
Hydramethylnon
分子式
C25H24F6N4
分子量
494.48

名称と別名

hydromethylnonDTXSID6023868CHEBI:2630NSC-379665AC-217300RefChem:788601DTXCID608102635,5-Dimethyl-perhydro-pyrimidin-2-one alpha-(4-trifluoromethylstyryl)-alpha-(4-trifluoromethyl)cinnamylidenehydrazone405-090-9614-073-7TETRAHYDRO-5,5-DIMETHYL-2(1H)-PYRIMIDINONE(3-(4-(TRIFLUOROMETHYL)PHENYL)-1-(2-(4-(TRIFLUOROMETHYL)PHENYL)ETHENYL)-2-PROPENYLIDENE)HYDRAZONE2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone
名称をさらに表示
3,4,5,6-テトラヒドロ-5,5-ジメチル-2(1H)-ピリミドン[3-[4-(トリフルオロメチル)フェニル]-1-[2-[4-(トリフルオロメチル)フェニル]エテニル]-2-プロペニリデン]ヒドラゾンコンバットアムドロマックスフォースヒドラメチルノンテトラヒドロ-5,5-ジメチル-2(1H)-ピリミジノン[p-(トリフルオロメチル)-α-[p-(トリフルオロメチル)スチリル]シンナミリデン]ヒドラゾンヒドラメチルノン標準品テトラヒドロ5,5ジメチル2(1H)ピリミジノン(p(トリフルオロメチル)α[p(トリフルオロメチル)スチリル)シンナミリデン]ヒドラゾンテトラヒドロ-5,5-ジメチル-2(1H)-ピリミジノン[P-トリフルオロメチル)-Α-[P-(トリフルオロメチル)スチリル]シンナミリデン]ヒドラゾン

物性

構造計算による物性

XLogP
6.4
極性表面積
48.8 Ų
水素結合供与体数
2
水素結合受容体数
8
回転可能結合数
6
重原子数
35
形式電荷
0
複雑度
763

実験および物理化学的性質

Chemical ClassesTeratogens
PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
Pesticides · 4 件

Pesticide -> EPA IRIS

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

LogP · 2 件

log Kow = 2.31

2.31

OdorCharacteristic of vegetable oil
Color/Form · 3 件

Yellow to tan crystals

Yellow-tan, free-flowing granules

Crystals from isopropanol

Solubility · 2 件

In acetone 360, ethanol 72, 1,2-dichloroethane 170, methanol 230, isopropanol 12, xylene 94, chlorobenzene 390 (all in g/L at 20 °C)

In water, 0.006 mg/L at 25 °C

Flash Point>220 °F (SFCC)
Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxide and hydrogen fluoride/

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P319, P330, P337+P317, P391, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P351+P338, P317, P318, P319, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Hazard Traits - Developmental Toxicity; Reproductive Toxicity

2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, [3-[4-(trifluoromethyl)phenyl]-1-[2-[4-(trifluoromethyl)phenyl]ethenyl]-2-propenylidene]hydrazone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, [3-[4-(trifluoromethyl)phenyl]-1-[2-[4-(trifluoromethyl)phenyl]ethenyl]-2-propenylidene]hydrazone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

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

2002/2076

REACH registered substance: 5,5-dimethyl-perhydro-pyrimidin-2-one α-(4-trifluoromethylstyryl)-α-(4-trifluoromethyl)cinnamylidenehydrazone (EC: 405-090-9)

Hydramethylnon: HSNO Approval: HSR003435 Approved with controls

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards SummaryAn eye irritant; [eChemPortal: ERMA; ESIS]

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

... The most abundant metabolite /in rats/ was CL 98,724: 1,5- bis(alpha,alpha,alpha-trifluoro-p-tolyl)-1,4-pentadien-3-one. ...

Sprague-Dawley rats were dosed with hydramethylnon ( ... CL 217,300) by gavage in corn oil at low (3 mg/kg) or high (100 mg/kg) single doses. Also, multiple-dosing was done with 14 consecutive daily treatments of 3 mg/kg, followed by 3 mg/kg of labeled hydramethylnon. In all cases, both phenyl and pyrimidinyl ring-labeled treatments were evaluated. There were no substantial differences associated with sex, dose level, or duration of treatment. ... The two main identified urinary metabolites were a substituted cinnamic acid and a substituted p-toluic acid. ... The major labeled component of tissues was parent compound, with appreciable amounts of moderately polar material as the second-most abundant fraction. ...

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 · 5 件

In rats, following oral admin, rapidly eliminated in the feces and urine.

No residues were detectable in the milk or tissues of goats (0.2 mg/kg in the daily diet for 8 days). No residues were found in the milk or tissues of cows (0.05 mg/kg for 21 consecutive days).

Sprague-Dawley rats were dosed with hydramethylnon ( ... CL 217,300) by gavage in corn oil at low (3 mg/kg) or high (100 mg/kg) single doses. Also, multiple-dosing was done with 14 consecutive daily treatments of 3 mg/kg, followed by 3 mg/kg of labeled hydramethylnon. In all cases, both phenyl and pyrimidinyl ring-labeled treatments were evaluated. There were no substantial differences associated with sex, dose level, or duration of treatment. Elimination was relatively rapid. Most of the label was excreted within 36 hr. Label was excreted principally in feces (about 90%). Parent compound was the major labeled fecal component (70-85% of administered doses ... ). Urinary elimination was about 1-4% of total administered compound ... . The two main identified urinary metabolites were a substituted cinnamic acid and a substituted p-toluic acid. Residues remaining in tissues after 7 days ranged from 3 to 10% of administered dose. The major labeled component of tissues was parent compound, with appreciable amounts of moderately polar material as the second-most abundant fraction. Data suggest inefficient absorption and a modest rate of metabolism of absorbed hydramethylnon. ...

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
ヒドラメチルノン STANDARD
ヒドラメチルノン Standard, 100 µg/mL in MeOH
2-(2-{1,5-ビス[4-(トリフルオロメチル)フェニル]ペンタ-1,4-ジエン-3-イリデン}ヒドラジン-1-イリデン)-5,5-ジメチル-1,3-ジアジナン
Hydramethylon
Matox
Wipeout
MAXFORCE
ac217300
cl217300
5,5-dimethyltetrahydropyrimidin-2(1H)-one (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)prop-2-en-1-ylidene)hydrazone67485-29-4AC 217300AmdroCL 217300CombatHydramethylnonJ265GZ7MFJ

データベース識別子

CAS
67485-29-4
PubChem CID
49901
DTXSID
DTXSID6023868
ChEMBL
CHEMBL464812
EC Number
405-090-9、614-073-7
Melting Point190 °C
Vapor Pressure · 3 件

0.00000002 [mmHg]

Yellow to tan crystalline solid with characteristic vegetable odor. MP 189-191 °C. Insoluble in water, slightly soluble in alcohols, and soluble in acetone, chorobenzene, and 1,2-dichloroethane. VP: 2X10-8 mm Hg at 25 °C. /Technical/

2.03X10-8 mm Hg at 25 °C

物理化学的性質

融点
185 · 185-190°C
沸点
510.5 · 510.5±60.0 °C(Predicted)
比重(密度)
1.2816 · 1.2816 (estimate)
蒸気圧
2.7 x · 2.7 x l0-6 Pa (25 °C)
貯蔵温度
0 · 0-6°C
溶解性
Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
水溶解度
0.005 · 0.005-0.007 mg l-1 (25 °C)
酸解離定数(Pka)
14.38 · 14.38±0.40(Predicted)
BRN
6015162 · 6015162
Henry's Law Constant
4.5 · 4.5×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
安定性
Light Sensitive
主な用途
農業環境
InChIKey
IQVNEKKDSLOHHK-FNCQTZNRSA-N
SMILES
CC1(C)CN\C(NC1)=N\N=C(\C=C\c2ccc(cc2)C(F)(F)F)/C=C/c3ccc(cc3)C(F)(F)F
CAS データベース
67485 · 67485-29-4(CAS DataBase Reference)
NISTの化学物質情報
2 · 2(1H)-pyrimidinone, tetrahydro-5,5-dimethyl-, (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone(67485-29-4)
EPAの化学物質情報
Hydramethylnon (67485-29-4)
化学的性質 · 1 件

化学的特性Yellow to orange crystal, solubility (25°C): water 0.005~0.007mg/L, (20°C) acetone 360g/L, chlorobenzene 390g/L, 1,2-dichloroethane 170g/L, ethanol 72g/L, methanol 230g/L, isopropanol 12g/L, xylene 94g/L. Stable at 25°C for 2 years, stable at 45°C for 90 days, decomposition by sunlight DT50 about 1 hour; fluorantrazone aqueous suspension is stable to hydrolysis, DT50 24-33 days (pH 4.9), 10-11 days (pH 7,03), 11-12 days (pH 8.87). Decomposition of DT50 in soil took about 6 days.

Reactive GroupAmines, Phosphines, and Pyridines
Special Reports · 1 件

USEPA/OPPTS; Reregistration Eligibility Decisions (REDs) Database on Hydramethylnon (67485-29-4). 155 pp. USEPA 738-R-98-023. Dec 1998. This document provides a thorough review of the scientific data underlying hydramethylnon's registration and fulfills the EPA's requirement to determine whether pesticides containing the active ingredient hydramethylnon are eligible for reregistration before calling in data on products.

FIFRA Requirements · 3 件

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6165]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing hydramethylnon. The Agency has completed its review of these generic data and has determined that the data are sufficient to support reregistration of all products containing hydramethylnon. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of hydramethylnon and lists the submitted studies that the Agency found acceptable. The data identified in Appendix B were sufficient to allow the Agency to assess the registered uses of hydramethylnon, and to determine that hydramethylnon can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing hydramethylnon as the active ingredient are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone is found on List B. Case No: 2585; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone; Data Call-in (DCI) Date(s): 4/12/91, 7/12/91, 3/3/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Reactivity ProfileHYDRAMETHYLNON is a trifluoromethyl amidinohydrazone.
Air and Water ReactionsInsoluble in water. Hydrolysis occurs rapidly at low and high pHs.
Hazard Classes and Categories · 6 件

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

Specific target organ toxicity (repeated exposure) - category 1

Acute toxicity (Oral) - Category 4

Teratogens

Acute Tox. 4 *

安全と保護具

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Fire Fighting ProceduresWater, foam, carbon dioxide, or dry chemical.
Storage Conditions · 2 件

Store in a cool, dry, secure place and keep container tightly closed. Use product within 3 months after opening for best results.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential uses/

Cleanup Methods · 3 件

Sweep up any spill and place in a closed container for disposal.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential uses/

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential uses/

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 3 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential uses/

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential uses/

Preventive Measures · 5 件

Users must follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.

User Safety Recommendations: Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing/PPE immediately if pesticide gets inside and then wash thoroughly and put on clean clothing. Remove PPE immediately after handling hydramethylnon, wash the outside of gloves before removing, and as soon as possible, wash thoroughly and change into clean clothing.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application.

For more Preventive Measures (Complete) data for HYDRAMETHYLNON (11 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Allowable Tolerances · 1 件

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6164]

Personal Protective Equipment (PPE) · 3 件

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

End Use Products Intended for Occupational Use (WPS and Non-WPS)): Applicators and other handlers must wear: long-sleeve shirt and long pants, water-resistant gloves, and shoes plus socks.

A 12-hour restricted entry interval (REI) is required. The PPE required for early entry is: coveralls, water resistant gloves, and shoes plus socks.

毒性情報

Target OrgansHepatic
Ecotoxicity Values · 5 件

LD50 /Anas platyrhynchos/ (Mallard duck) oral >2,510 mg/kg

LD50 /Colinus virginianus/ (Bobwhite quail) oral 1,828 mg/kg

LC50 Anas platyrhynchos (Mallard duck, age 14 days) diet 4355 ppm for 8 days (95% confidence interval: 2877-6592 ppm)[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on Tetrahydro-5,5-dimethyl-2(1H)-pyrimidio[3-[4-Trifluoromethyl)phenyl]-1-[2-

LC50 Colinus virginianus (Northern bobwhite, age 14 days) diet 1136 ppm for 8 days (95% confidence interval: 908-1420 ppm)[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on Tetrahydro-5,5-dimethyl-2(1H)-pyrimidio[3-[4-Trifluoromethyl)phenyl]-1-[2-

For more Ecotoxicity Values (Complete) data for HYDRAMETHYLNON (32 total), please visit the HSDB record page.

Environmental Fate · 4 件

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 3,300 and 8,677(2) indicate that hydramethylnon is expected to have very slight to no mobility in soil(SRC). Volatilization of hydramethylnon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.20X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 2.03X10-8 mm Hg(3), and water solubility, 6.0X10-3 mg/L(3). Hydramethylnon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Photolysis on soil is diphasic with a half-life of 4 days for the first phase and about 30 days for the second phase(2). A biodegradation half-life for aerobic soil metabolism of 385 days(2) suggests that biodegradation is not an important environmental fate process in soil(SRC).

TERRESTRIAL FATE: The half-life of hydramethylnon in sandy loam was approximately 7 days, 28 days when incorporated into the soil(1). Using test field plots in Florida and Texas, half-lives of 3 days and 55, respectively, were observed with no detections below the 0-6 inch soil depth. Hydramethylnon is reported as persistent and immobile below soil surfaces(2).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 3,300 and 8,677(2) indicate that hydramethylnon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.03X10-8 mm Hg(4), and water solubility, 6.0X10-3 mg/L(4). The photolysis half-lives in aqueous suspension at 25 °C have been reported as 24-33 days (pH 9), 10-11 days (pH 7.02), and 11-12 days (pH 8.87)(4). According to a classification scheme(5), a BCF of 1,300(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). The half-life for anaerobic aquatic metabolism ranges from 445 to 552 days(2) which suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydramethylnon, which has a vapor pressure of 2.03X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hydramethylnon is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3 hrs(SRC), calculated from its rate constant of 1.35X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hydramethylnon may be removed from the air by wet or dry deposition(SRC). Hydramethylnon is rapidly degraded in sunlight by photolysis, with a half-life of approximately 1 hour(2).

Food Survey ValuesNegligible residues of hydramethylnon were found in radishes, barley, and french beans planted three months after treatment of the soil(1).
Milk Concentrations · 1 件

EXPERIMENTAL: No residues of hydramethylnon were detectable in the milk of goats after being exposed to 0.2 mg/kg hydramethylnon in the daily diet for 8 days(1). No residues were found in the milk of cows after being exposed to 0.05 mg/kg hydramethylnon for 21 consecutive days(1).

Ecotoxicity Excerpts · 4 件

/BIRDS and MAMMALS/ An acute oral toxicity study using the technical grade of the active ingredient (TGAI) was conducted to establish the toxicity of hydramethylnon to birds. In Northern bobwhite quail (Colinus virginianus) administered 92% a.i. the LD50 was 1828 mg/kg, leading EPA to conclude that the substance was slightly toxic to bobwhite quail. In Mallard duck (Anas platyrhynchos) administered 92% a.i. the LD50 was 2510 mg/kg, leading EPA to conclude that the substance was practically nontoxic to Mallard ducks. Two avian subacute toxicity tests were also available. In Northern bobwhite quail (Colinus virginianus) 92% a.i. had an 5-day LC50 of 1136 ppm and in Mallard duck (Anas platyrhynchos) 92% a.i. had a 5-day LC50 of 4355 ppm. EPA judged both studies as showing hydramethylnon to be slightly toxic.

/BIRDS and MAMMALS/ Wild mammal testing is required /by EPA for pesticides/ on a case-by-case basis, depending on the results of lower tier laboratory mammalian studies, intended use pattern and pertinent environmental fate characteristics. In most cases, rat or mouse toxicity values obtained from the Agency's files substitute for wild mammal testing. ... In the Norway Rat (Rattus norvegicus), 95% a.i. administered orally produced an LD50 of 817 mg/kg (m) and 1502 mg/kg (f); combined: 1146 mg/kg; EPA considered this information that hydramethylnon is slightly toxic in an acute oral test. In a 3-generation reproductive study in Norway Rat (Rattus norvegicus), administration of 92% a.i. resulted in male infertility at 100 ppm.

/AQUATIC SPECIES/ Two freshwater fish toxicity studies using the technical grade active ingredient were required by EPA to establish the toxicity of hydramethylnon to fish. Three acute studies of 92% a.i. were available. The 96 hr LC50s indicated that hydramethylnon is highly toxic to Rainbow trout (Oncorhynchus mykiss), moderately toxic to Bluegill sunfish (Lepomis macrochirus), and very highly toxic to Channel catfish (Ictalurus punctatus). In a freshwater aquatic invertebrate toxicity test, a 48-hour LC50/ EC50 of 1.14 ppm indicated that the 92% a.i. was moderately toxic to the waterflea (Daphnia magna).

/OTHER TERRESTRIAL SPECIES/ A honey bee acute contact study using the technical grade active ingredient was required for hydramethylnon because its outdoor use may result in honey bee exposure. The LD50 of 68.0 g/bee using 96.8% a.i. demonstrated that hydramethylnon is practically non-toxic to bees on an acute contact basis.

Plant ConcentrationsResidues of hydramethylnon in grass four months after treatment were <0.01 ppm(1).
Animal Concentrations · 1 件

No residues of hydramethylnon were detectable in tissues of goats after being exposed to 0.2 mg/kg hydramethylnon in the daily diet for 8 days(1). No residues were found in tissues of cows after being exposed to 0.05 mg/kg hydramethylnon for 21 consecutive days(1).

Acute Toxicity LinkChemical: AMDRO
EPA IRIS Information · 3 件

Amdro

Hepatic

3 x 10 ^-4 mg/kg-day

Soil Adsorption/Mobility · 1 件

Koc values of hydramethylnon have been reported as ranging from 3,300 to 8,677 using loamy sand, sandy loam, loam and silt loam soils, with reported Kds of 1,039-1,782 mL/g(1). According to a classification scheme(2), these Koc values suggest that hydramethylnon is expected to be slightly mobile to immobile in soil.

Artificial Pollution SourcesHydramethylnon'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).

法規制情報

FIFRA Requirements · 3 件

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6165]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing hydramethylnon. The Agency has completed its review of these generic data and has determined that the data are sufficient to support reregistration of all products containing hydramethylnon. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of hydramethylnon and lists the submitted studies that the Agency found acceptable. The data identified in Appendix B were sufficient to allow the Agency to assess the registered uses of hydramethylnon, and to determine that hydramethylnon can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing hydramethylnon as the active ingredient are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone is found on List B. Case No: 2585; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone; Data Call-in (DCI) Date(s): 4/12/91, 7/12/91, 3/3/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

安全データ

wgk
3
rtecs
UW7583000
ridadr
UN3077 9/PG 3
risk_code
22-36-48/25-50/53
化審法
一般化学物質
hazard_code
T;N,N,T
safety_code
1/2-22-26-36/37-45-60-61
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2STOT RE 1 Oral
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
67485-29-4(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=1

... This rat study found that 71.5% of oral dose was eliminated in feces unchanged. The lesser amounts of label found in urine yielded no parent compound, but rather a number of polar metabolites. In tissues sampled (including liver), parent compound was generally the most abundant labeled moiety. The most abundant metabolite was CL 98,724: 1,5- bis(alpha,alpha,alpha-trifluoro-p-tolyl)-1,4-pentadien-3-one. ...

For more Absorption, Distribution and Excretion (Complete) data for HYDRAMETHYLNON (6 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used as slow-acting stomach poison insecticide for control of ants and cockroaches; [HSDB]

Farming (Pesticides) [Category: Industry]

For hydramethylnon (USEPA/OPP Pesticide Code: 118401) 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 for ants (big headed, fire, harvester)

Slow activating stomach poison insecticide

A slow-acting toxicant used successfully in bait for the fire ant, other ants, and cockroaches

U.S. Production2023: <50,000 lb
Industry UsesIntermediate
Methods of Manufacturing4-(Trifluormethylbenzaldehyde) + acetone + hydrazine + neopentyl glycol + urea (carbonyl condensation/ imine formation/ condensation/ imine formation)
Formulations/Preparations · 5 件

Formulations: Oil bait

AMDRO GRANULAR INSECTICIDE: Active Ingredient 0.88% Hydramethylnon

AMDRO 20 FIREANT INSECTICIDE: Active Ingredient 0.88% Hydramethylnon.

HYDRAMETHYLNON TECHNICAL INSECTICIDE: Active Ingredient 98% Hydramethylnon.

For more Formulations/Preparations (Complete) data for HYDRAMETHYLNON (38 total), please visit the HSDB record page.

Household ProductsInformation on 15 consumer products that contain Hydramethylnon in the following categories is provided:
Use ClassificationINSECTICIDES
General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing

Registered for the control of ants in grasses and non-crop lands such as lawns, turfs, and non-bearing nursery stocks. Also registered for the control of ants and cockroaches in non-food use areas in domestic dwellings and commercial establishments.

応用分野 · 5 件

用途農薬(殺虫剤)

説明Hydramethylnon is an organic pesticide active ingredient from the trifluoromethyl aminohydrazone chemical class. It is a registered chemical alternative for chlorpyrifos for use as a termiticide and against ants, crickets, and cockroaches around the home and lawn. Hydramethylnon is also used in a wide variety of professional pesticide products and in various formulations, These include foaming products, granular products, gel baits, liquid concentrates.

来歴Hydramethylnon was developed by DuPont in 1975 and introduced to ornamentals industry in the 1990s. Acequinocyl was also discovered by DuPont in the 1970s and further developed by AgroKanesbo Co. Ltd. and Tomen Agro in Japan. Arysta LifeScience first introduced acequinocyl to the U.S. ornamentals market in 2005. Bifenazate was first developed by Uniroyal Chemical in 1990 and commercialized by Crompton Corporation in 1999. Bifenazate was introduced to the ornamental market in 2010.

使用Hydramethylon is an insecticide primarily used in the form of baits for cockroaches and ants.

一般的な説明Hydramethylnon appears as odorless yellow crystals. Insoluble in water. Used as an insecticide.

調製方法

製造方法Hydramethylnon synthesis was achieved through the coupling in alcoholic media refluxing the compound 1,5-bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one afforded the desired product in 50% yield.Synthesis of hydramethylnon

上流・下流製品情報

上流原料

ヘキサメチレンテトラミン4-(トリフルオロメチル)ベンズアルデヒド

サプライヤー100 社

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補足説明 · 1 件

定義ChEBI: Hydramethylnon is a member of the class of hydrazones that is used as an insecticide for control of ants and cockroaches. It has a role as a mitochondrial cytochrome-bc1 complex inhibitor and an insecticide. It is a hydrazone, a member of pyrimidines, a member of (trifluoromethyl)benzenes, an olefinic compound and a member of guanidines.