N,N-ジメチル-N'-フェニル尿素

Fenuron

HCID 7560

基本情報

CAS
101-42-8
標準SMILES
CN(C)C(=O)Nc1ccccc1
InChIKey
XXOYNJXVWVNOOJ-UHFFFAOYSA-N
分子式
C9H12N2O
平均分子量
164.2 g/mol
単同位体質量
164.09496301

概要

Fenuron is a member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a phenyl group while the other is substituted by two methyl groups. It is a herbicide used for the control of weeds in beetroot as well as various vegetable and ornamental crops. It has a role as a herbicide, a photosystem-II inhibitor, an agrochemical, a xenobiotic and an environmental contaminant.

名称と識別子

優先名称
Fenuron
IUPAC
1,1-dimethyl-3-phenylurea
現地名
N,N-ジメチル-N'-フェニル尿素
英語名
FENURON
分子式
C9H12N2O
分子量
164.2

名称と別名

FENURON1,1-Dimethyl-3-phenylurea101-42-8FalisilvanDybarDibarN,N-Dimethyl-N'-phenylureaUrea, N,N-dimethyl-N'-phenyl-Fenidin3-Phenyl-1,1-dimethylureaAmicure URQuintex
名称をさらに表示
1,1-ジメチル-3-[フェニル]尿素N,N-ジメチル-N'-フェニル尿素1-フェニル-3,3-ジメチル尿素フェヌロンフェニュロンジバル1,1-ジメチル-3-フェニル尿素フェヌロン標準品フェニュロン STANDARDフェニュロン Standard, 0.1 mg/mL in Acetonitrileフェニュロン Standard, 100 µg/mL in MeOHN,N-ジメチル-N′-フェニル尿素3,3-ジメチル-1-フェニル尿素redPUDPDUDYRK5KAYRONPDU(R)
Omicure 94Croptex ChromeHerbon YellowCroptex RubyN-Phenyl-N',N'-dimethylureaPUD (herbicide)1-Phenyl-3,3-dimethylureaFikure 62U

データベース識別子

CAS
101-42-8
PubChem CID
7560
DTXSID
DTXSID7037551
ChEMBL
CHEMBL1492698
ChEBI
CHEBI:5013
UNII
O7L040435W
EC Number
202-941-4
Nikkaji
J8.623A

物性

構造計算による物性

XLogP
1
極性表面積
32.3 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
12

実験および物理化学的性質

SpringerMaterials PropertiesBoiling point
Pesticides · 5 件

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Urea Derivative

Pesticide (Fenuron) -> USDA PDB

Pesticide

LogP1.18
Density1.08 at 20 °C/20 °C
Color/Form · 3 件

White, crystalline solid

Colorless crystalline solid

Colorless crystals

Solubility · 6 件

Sol in water 4.8 g/l at room temperature. Moderately sol in acetone and aromatic solvents. sparingly soluble in petroleum oils. /Fenuron trichloroacetate/

3850 ppm @ 25 °C

Sparingly sol in water (0.29% at 24 °C)

Solubility (25 °C): 3.85 g/l water; sparingly soluble in hydrocarbons.

In ethanol 108.8, diethylether 5.5, acetone 80.2, benzene 3.1, chloroform 125, n-hexane 0.2, groundnut oil 1.0 (all in g/kg at 20-25 °C)

In water 3.85 g/l at 25 °C

物理化学的性質

融点
131 · 131-133°
沸点
291.67 °C · 291.67°C (rough estimate)
比重(密度)
1.1062 · 1.1062 (rough estimate)
蒸気圧
0.002 Pa · 0.002Pa at 60℃
屈折率
1.5373 · 1.5373 (estimate)
闪点
2 °C · 2 °C

化学的性質

化学的特性White, crystalline solid. Almost insoluble in water (0.3% at 25C), sparingly soluble in hydrocarbon solvents, stable toward oxidation and moisture.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 12.6% (25 of 199) of reports.

Warning

H319 (27.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P261, P264+P265, P271, P273, P280, P304+P340, P305+P351+P338, P318, P319, P337+P317, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 199 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Urea, N,N-dimethyl-N'-phenyl-

Urea, N,N-dimethyl-N'-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Urea, N,N-dimethyl-N'-phenyl- 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)

REACH registered substance: Fenuron (EC: 202-941-4)

Urea, N,N-dimethyl-N'-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Urea-derived herbicides have low toxicity in animal feeding studies; May induce methemoglobinemia; After daily doses of 150 mg/kg for 10 months, guinea pigs had anemia, hypothyroidism, and injury to the liver, kidneys, and heart; No effects in rats fed 500 ppm for 90 days; [HSDB] Systemic toxicity unlikely unless large amounts ingested; [EPA Pesticides, p. 122] May be hydrolyzed to aniline causing methemoglobinemia; [Merck Index] May cause irritation; May induce methemoglobinemia; [MSDSonline]

Hazard Classes and CategoriesEye Irrit. 2 (27.1%)
Skin, Eye, and Respiratory IrritationsNon-irritating to skin

安全と保護具

Disposal MethodsThe products /of decomposition/ ... are both toxic, thus precluding hydrolysis as a disposal method.

毒性情報

Ecotoxicity ValuesLC50 Guppy 610 mg/l/48 hr /Conditions of bioassay not specified/
Environmental Fate · 4 件

TERRESTRIAL FATE: In soil, enzymic and microbial degradation involves step by step N-demethylation.

TERRESTRIAL FATE: The complete degradation of fenuron in soil has been experimentally determined to be 4.5 months at 15 °C and 2.2 months at 30 °C(1). Biodegradation will be the primary fate process in soil(2). Measured Kocs of 27(3) and 43(4) indicate that adsorption to soil will not be important(SRC). A visible change in color occurred within 2 hours when paper saturated with fenuron was exposed to sunlight(5) suggesting that some fenuron may be removed from soil surfaces via direct photolysis(SRC).

AQUATIC FATE: After 2 weeks, approximately 20% of 10 ug/L fenuron remained in raw river water samples exposed to sunlight and artificial fluorescent light(1). Biodegradation is expected to be the primary fate process in aquatic ecosystems(2,SRC). Measured Kocs of 27(3) and 43(4) indicate that adsorption of fenuron from the water column to sediment and suspended material will not be important(SRC). An estimated BCF of 6(3) indicates that fenuron will not bioconcentrate in fish(SRC). A visible change in color occurred within 2 hours when paper saturated with fenuron was exposed to sunlight(5) suggesting that some fenuron may be removed from water via direct photolysis(SRC). Volatilization from water will not be important(7) based on a low Henry's Law constant of 1.68X10-10 atm-cu m/mole at 25 °C(6,SRC).

ATMOSPHERIC FATE: Based on a measured water solubility of 4,027 mg/L at 25 °C(1) and an estimated Henry's Law constant of 9.71X10-10 atm-cu m/mole at 25 °C(2), the vapor pressure of fenuron can be estimated to be 1.81E-5 mm Hg at 25 °C(SRC). This vapor pressure value suggests that fenuron will exist in the vapor and particulate phases in the ambient atmosphere(3). Vapor-phase fenuron is rapidly degraded in the ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for this reaction in air can be estimated to be about 2.3 hrs(4,SRC). A visible change in color occurred within 2 hours when paper saturated with fenuron was exposed to sunlight(5) suggesting that fenuron may be removed from the atmosphere via direct photolysis(SRC). Particulate-phase fenuron is removed via dry deposition(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Plant ConcentrationsIn plants, N-demethylation occurs step by step.
Soil Adsorption/MobilityAverage Koc values of about 27(1) and 43(2) have been experimentally determined for fenuron. Based on a suggested classification scheme(3), these Koc values indicate that fenuron will have very high soil mobility.
Artificial Pollution SourcesFenuron is released to the environment during its use as a herbicide(1).

安全データ

wgk
2
tsca
TSCA listed
rtecs
YT1450000
ridadr
UN 1648 3/PG 2
毒性
LD50 orally in rats: 7500 mg/kg (Bailey, White)
hs_code
29242990

化学と産業

薬理情報

Mechanism of ActionInhibits photosynthesis.
Metabolism/MetabolitesDealkylation and hydroxylation of aromatic ring of phenylureas take place during animal metabolism.
Absorption, Distribution and ExcretionNonselective systemic herbicide, absorbed predominantly by the roots, with translocation acropetally in the xylem.

用途と製造

Uses · 5 件

Used as herbicide to control woody plants and perennial weeds (especially on non-crop land); [HSDB]

Farming (Pesticides) [Category: Industry]

Weed and brush killer.

Herbicide

Control of woody plants and deep rooted perennial weeds, particularly on non crop land. Often used in combination with chloropropham to extend the weed spectrum and range of crops.

U.S. Production2023: 25,000 - <50,000 lb
Consumer UsesAdhesion/cohesion promoter
Industry UsesCatalyst
Formulations/Preparations · 3 件

May be supplied in combination with other herbicides such as chlorpropham or propham. Also supplied as the salt of trichloroacetic acid.

Croptex Chrome, Croptex Ruby, Red, Herbon Yellow (fenuron + chloropropham); Electrum (20 g fenuron + 240 g chloridazon + 30 g chloropropham + 120 g propham/l); Gold, Premalox, Quintex (fenuron + chlroopropham + propham/l)

Wettable powder

General Manufacturing Information · 2 件

All Other Chemical Product and Preparation Manufacturing

Urea, N,N-dimethyl-N'-phenyl-: ACTIVE

応用分野

使用Fenuron is an phenylurea based herbicide used to control brush on chaparral watersheds.

サプライヤー100 社

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
楗桥化学(上海)有限公司13248325872
北京福源坊科技有限公司010-57903446 15869909019 · [email protected]

補足説明

定義electrum: 1. An alloy of gold andsilver containing 55–88% of gold.2. A German silver alloy containing52% copper, 26% nickel, and 22%zinc.

関連反応

4 件

化合物ノート

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