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炭酸1-メチルエチル2-(1-メチルプロピル)-4,6-ジニトロフェニル

Dinobuton

HCID 13783
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
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基本情報

CAS
62655-72-5
標準SMILES
CCC(C)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)OC(C)C
InChIKey
HDWLUGYOLUHEMN-UHFFFAOYSA-N
分子式
C14H18N2O7
平均分子量
326.3 g/mol
単同位体質量
326.11140092

概要

Dinobuton is a C-nitro compound.

名称と識別子

優先名称
Dinobuton
IUPAC
(2-butan-2-yl-4,6-dinitrophenyl) propan-2-yl carbonate
現地名
炭酸1-メチルエチル2-(1-メチルプロピル)-4,6-ジニトロフェニル
英語名
DINOBUTON
分子式
C14H18N2O7
分子量
326.3

名称と別名

Dinobuton973-21-7DrawinolAcrexDinofenKasebonSytasolAkrexTalanDESSINIsophen (pesticide)Union Carbide 19786
名称をさらに表示
ジノフェン炭酸(2-sec-ブチル-4,6-ジニトロフェニル)イソプロピルアクレックス炭酸1-メチルエチル2-(1-メチルプロピル)-4,6-ジニトロフェニルタランデッシンジノブトン2-(ブタン-2-イル)-4,6-ジニトロフェニル プロパン-2-イル カルボナートCPBAmc1053ds18302oms1056
2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonateDTXSID4040268MC 1053UC 19786OMS 1056A711XEV1PFENT 27,2442,4-Dinitro-6-sec-butylphenyl isopropyl carbonate

データベース識別子

CAS
62655-72-5、973-21-7
PubChem CID
13783
DTXSID
DTXSID4040268
ChEMBL
CHEMBL1358468
ChEBI
CHEBI:81914
UNII
A711XEV1PF

物性

構造計算による物性

XLogP
4.3
極性表面積
127 Ų
水素結合供与体数
0
水素結合受容体数
7
回転可能結合数
6
重原子数
23
形式電荷
0
複雑度
443

実験および物理化学的性質

Pesticides · 3 件

Acaricides, Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

Color/Form · 2 件

CRYSTALS FROM METHANOL OR PETROLEUM ETHER

PALE YELLOW SOLID

Solubility · 2 件

SOL IN ALIPHATIC HYDROCARBONS, ETHANOL, FATTY OILS; HIGHLY SOL IN LOWER ALIPHATIC KETONES, AROMATIC HYDROCARBONS

In water, 0.1 mg/100 ml at 20 °C. In acetone 120, ethanol 8.3, xylene 89, n-hexane 1.9 (all in g/100 ml at 20 °C)

CorrosivityNon-corrosive
Melting Point · 2 件

56-57 °C

MP: 58-60 °C; NONCORROSIVE /TECHNICAL PRODUCT, 97% PURE/

Vapor Pressure · 2 件

0.0000011 [mmHg]

Less than 10-5 mbar at 20 °C

Physical DescriptionPale yellow solid; [HSDB] Yellowish crystalline solid; [MSDSonline]
Other Experimental PropertiesHYDROLYZED BY ALKALI TO PARENT PHENOL DINOSEB

物理化学的性質

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

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Hazards Summary · 1 件

A metabolic stimulant that causes weight loss in high-dose animal studies; NOAEL for dogs is 4.5 mg/kg daily; [HSDB] One of the nitrocresolic compounds that can cause fatal poisonings after dermal contamination; Effects include uncoupling oxidative phosphorylation, acute hyperthermia, liver and kidney injury, and yellow staining of skin; [EPA Pesticides, p. 104-5] May cause irritation, GI disturbances, and cyanosis; May cause injury to cardiovascular system, kidneys, and liver; [MSDSonline] See Dinocap.

DOT Hazard Classification · 2 件

Dinobuton

Marine pollutant

Hazard Classes and Categories · 3 件

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute Tox. 3 *

安全と保護具

Storage ConditionsFORMULATION SHOULD NOT BE STORED BELOW ZERO.
Disposal Methods · 2 件

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.

化学と産業

薬理情報

Mechanism of ActionPESTICIDES AT 0.1 TO 0.01 MEAN LC50 AFFECTED PEROXIDASE ACTIVITY IN SCALY CARP YEARLINGS. ACREX CAUSED BIPHASIC RESPONSE (STIMULATION & NORMALIZATION).
Metabolism/Metabolites · 5 件

TWENTY-EIGHT DAYS AFTER TOPICAL APPLICATION...TO APPLE FRUITS, ABOUT 75 /%/...LOST. ANALYSES OF PEEL INDICATED PRESENCE OF...2-AMINO-6-SEC-BUTYL-4-NITROPHENOL & 3-(3,5-DINITRO-2-HYDROXYPHENYL)BUTYRIC ACID.

...STUDIES WITH [RING-(14)C]DINOBUTON. TREATMENT OF WATER-SOL MATERIALS WITH BETA-GLUCOSIDASE &/OR GLUSULASE LIBERATED SIGNIFICANT PERCENTAGE OF (14)C ACTIVITY AS ETHER-EXTRACTABLE METABOLITES. TLC OF...EXTRACTS REVEALED PRESENCE OF DINOSEB, 4-AMINO-6-NITRO-2-SEC-BUTYLPHENOL, 6-AMINO-4-NITRO-2-SEC-BUTYLPHENOL, & OTHER UNIDENTIFIED PRODUCTS.

AFTER INJECTION OF DINOBUTON INTO STEMS OF BEAN PLANTS, DNBP /DINITRO-ORTHO-SEC-BUTYLPHENOL/, 4-NH2-NBP /4-AMINO-6-NITRO-2-SEC-BUTYLPHENOL/, & 6-NH2-NBP /6-AMINO-4-NITRO-2-SEC-BUTYLPHENOL/...OBSERVED IN CONJUGATED FORM AS BETA-GLUCOSIDES. SOME CO2 RELEASED BY HYDROLYSIS...WAS ALSO INCORPORATED INTO PLANT MATERIALS.

IN FRESH SHEEP RUMEN FLUID, DINOBUTON WAS RAPIDLY DECOMPOSED. SIMULTANEOUSLY, AMT OF 6-ANBP INCR. DIAMINOPHENOL (DABP) WAS END PRODUCT OF RUMINAL METABOLISM.

For more Metabolism/Metabolites (Complete) data for DESSIN (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 1 件

[CARBONYL-(14)C]DINOBUTON...WAS RAPIDLY HYDROLYZED IN ORALLY TREATED MICE & RATS... RATS EXCRETED VIRTUALLY ALL OF DOSE OF [PHENYL-(14)C] DINOBUTON IN 72 HR, BUT MICE EXCRETED LESS (74%); MORE THAN ONE-HALF OF URINARY LABEL IN BOTH...WAS POLAR MATERIAL...BUT SMALL AMT OF TWO AMINO-PHENOLS & TWO CARBOXYLIC ACIDS...IDENTIFIED

用途と製造

Uses · 5 件

Used as non-systemic acaricide, fungicide, and miticide; [HSDB]

Farming (Pesticides) [Category: Industry]

NON-SYSTEMIC ACARICIDE & FUNGICIDE

Miticide

Non-systemic acaricide, principally for control of motile stages of spider mites, with secondary fungicidal activity. Used for the control of spider mites in fruit, vegetable, hop, and vine cultivation. Control of powdery mildew on pome fruit and cucumbers. Also recommended for glasshouse use.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

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
EC Number
213-546-1
Nikkaji
J3.356A
融点
61 · 61-62℃
沸点
464.35 °C · 464.35°C (rough estimate)
比重(密度)
1.2731 · 1.2731 (rough estimate)
屈折率
1.511 · 1.5110 (estimate)
水溶解度
水に不溶
Merck
13 · 13,3315
BRN
2065340 · 2065340
Henry's Law Constant
6.2 · 6.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
CAS データベース
973 · 973-21-7
EPAの化学物質情報
Dinobuton (973-21-7)

Dinobuton is easily converted by hydrolysis into the corresponding dinitrophenol (dinoseb) which is even more toxic than the original product. Incineration is suggested at 1000 °C (2.0 sec minimum) with adequate scrubbing equipment for the removal of NO(x). Recommendable method: Incineration. Not recommendable method: Hydrolysis.

Personal Protective Equipment (PPE)GLOVES & RESPIRATOR FILTER.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6800(SRC), determined from a structure estimation method(2), indicates that Dessin will be immobile in soil(SRC). Dessin may biodegrade under anaerobic conditions; in ruminal fluid, this compound was rapidly degraded(3). In alkaline water, this compound should hydrolyze to dinoseb(4). Volatilization of Dessin is not expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC), using a recommended regression equation(5). Volatilization should not occur from dry soil surfaces(SRC), based on an estimated vapor pressure of 1.1X10-6 mm Hg(SRC), determined from a fragment constant method(6). Photodegradation of Dessin on soil surfaces may occur; dessin, exposed to sunlight on bean foliage, formed several degradation products(7).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6800(SRC), determined from a structure estimation method(2), indicates that Dessin should adsorb to suspended solids and sediment in water(SRC). Dessin may biodegrade under anaerobic conditions; in ruminal fluid, this compound was rapidly degraded(3). In alkaline water, this compound should hydrolyze to the parent compound, dinoseb(4). Dessin is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC), developed from a fragment constant estimation method(5). An estimated BCF value of 580(1,SRC), from an estimated log Kow(6,SRC), suggests that Dessin will bioconcentrate in aquatic organisms(SRC), according to a classification scheme(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Dessin, which has an estimated vapor pressure of 1.1X10-6 mm Hg at 25 °C(2,SRC), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Dessin 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 about 2 days(3,SRC). Particulate-phase Dessin may be physically removed from the air by 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.
Acute Toxicity LinkChemical: DINOBUTON
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for Dessin can be estimated to be about 6800(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that Dessin will be immobile in soil(SRC).

Human Toxicity Excerpts · 1 件

STATE OF IMMUNOLOGICAL REACTIVITY IN 70 FEMALE HOTHOUSE WORKERS WITH PROLONGED EXPOSURE TO PESTICIDES WAS EVALUATED. ANALYSIS OF INDICES OF NONSPECIFIC IMMUNITY SHOWED INCR MICROBIAL DISSEMINATION OF THE SKIN. THE DEGREE OF DISSEMINATION WAS CORRELATED WITH DURATION OF EXPOSURE TO PESTICIDES. WORKERS WITH OVER 2 YR EXPOSURE HAD SIGNIFICANTLY DECR PHAGOCYTIC ACTIVITY OF NEUTROPHILS. SPECIFIC INCR OF BLAST TRANSFORMATION OF PERIPHERAL BLOOD LYMPHOCYTES IN RESPONSE TO ACREX (DINOBUTON) WAS DETECTED IN 47-52% OF WORKERS WITH OVER 5 YR EXPOSURE. GENERAL MORBIDITY INCREASED WITH INCREASE OF DURATION OF EXPOSURE: ALLERGIC SKIN DISEASES WERE MORE FREQUENT AMONG WORKERS WITH 1-5 YR EXPOSURE, WHILE BRONCHIAL ASTHMA, LIVER & KIDNEY DISEASES WERE MORE FREQUENT AMONG WORKERS WITH OVER 5 YR EXPOSURE.

Artificial Pollution SourcesDessin's use as a non-systemic acaricide, fungicide(1), and miticide(2) will result in its direct release to the environment(SRC).
Environmental Biodegradation · 1 件

Dessin, was rapidly metabolized when incubated with bovine ruminal fluid. Metabolites tentatively identified were 2-amino-6-sec-butyl-4-nitrophenol and the 2,4-diamino-6-sec-butylphenol. The latter compound apparently is the end product of the ruminal metabolism of dessin(1).

Environmental Bioconcentration · 1 件

An estimated BCF value of 580 was calculated for Dessin(SRC), using an estimated log Kow of 3.94(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for Dessin is estimated as 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that Dessin will not volatilize from water surfaces(2,SRC). Dessin's estimated values for vapor pressure, 1.1X10-6 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).

Non-Human Toxicity Excerpts · 2 件

MAX 'NO EFFECT' LEVEL FOR DOGS IS 4.5 MG/KG DAILY, FOR RATS 3-6 MG/KG DAILY. IT ACTS AS METABOLIC STIMULANT, HIGH DOSES CAUSING LOSS OF BODY WT.

PROLONGED FEEDING OF ACREX (FODDER CONTAINING 30% EMULSIFIABLE CONCN FOR 2 MO TO SHEEP; DAILY DOSE OF 35 MG/KG-GROUP 1, 16.6 MG/KG-GROUP 2, OR 8.3 MG/KG-GROUP 3) INDUCED HYPEREMIA OF ORAL MUCOSA, SPLOTCHY LIVER COLORING, CATARRHAL INFLAMMATION OF STOMACH & INTESTINE, HEMORRHAGIC FOCI IN HEART MUSCLE, & ATRIAL HYPOTROPHY. EXPOSURE ALSO RESULTED IN DECR OF RED BLOOD COUNT & TOTAL PROTEIN IN BLOOD SERUM.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of Dessin with photochemically-produced hydroxyl radicals has been estimated as 7.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Anthraquinone enhanced the photodegradation of dessin(2). Bean leaves sprayed with both rotenone and Dessin and then exposed to sunlight for 1 hour gave a 14-C-dessin recovery of 80.8, 67.2, and 29.9% at rotenone concentrations of 0, 10, and 100 ppm, respectively; this suggests that rotenone may act as a photosensitizer to Dessin(3). Dessin, exposed to sunlight on bean foliage, formed several degradation products including dinoseb, one unknown ester and two unknown phenol compounds(4). This compound decomposes under alkaline conditions to dinoseb(5).

Probable Routes of Human ExposureDuring the airblast spraying of fruit orchards workers are exposed to Dessin through both respiratory and dermal routes, potentially at concentrations of 0.02 mg/hr and 31.0 mg/hr, respectively(1).

安全データ

wgk
3
rtecs
FF9100000
ridadr
2779
毒性
LD50 in male, female rats (mg/kg): 59, 71 orally (Gaines)
hs_code
29209090
risk_code
25-50/53
hazard_code
T,N
safety_code
37-45-60-61
hazard_class
6.1(b)
packing_group
III
有毒物質データの
973-21-7(Hazardous Substances Data)
Methods of Manufacturing · 2 件

...BY CONDENSATION OF ALKALI SALT OF DINOSEB WITH ISOPROPYL CHLOROFORMATE.

Production is by esterification of 2-sec-butyl-4,6-dinitrophenol with isopropyl chloroformate.

Formulations/PreparationsWETTABLE PRODUCTS 50%; AQ SUSPENSION 50%; ATOMIZING CONCENTRATES; EMULSIFIABLE CONCENTRATES 30%.
Use ClassificationACARICIDES
General Manufacturing Information · 2 件

IT IS NON-CORROSIVE BUT, TO PREVENT HYDROLYSIS, ALKALINE COMPONENTS MUST BE AVOIDED IN ITS FORMULATION. IT IS COMPATIBLE WITH NON-ALKALINE PESTICIDES BUT IT IS DEACTIVATED BY CARBARYL.

NON-SYSTEMIC ACARICIDE & IS A FUNGICIDE ACTIVE AGAINST POWDERY MILDEWS. GLASSHOUSE & FIELD USE AGAINST RED SPIDER MITES & POWDERY MILDEW OF APPLES, COTTON, AND VEGETABLES AT 0.05%.

応用分野

使用Dinobuton is a non-systemic fungicide, active against powdery mildews in apples, cotton and vegetables.

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