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디노부톤

Dinobuton

HCID 13783
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
62655-72-5
표준 SMILES
CCC(C)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)OC(C)C
InChIKey
HDWLUGYOLUHEMN-UHFFFAOYSA-N
분자식
C14H18N2O7
평균 분자량
326.3 g/mol
단동위원소 질량
326.11140092

개요

Dinobuton is a C-nitro compound.

이름 및 식별자

우선 이름
Dinobuton
IUPAC
(2-butan-2-yl-4,6-dinitrophenyl) propan-2-yl carbonate
현지명
디노부톤
영어명
DINOBUTON
분자식
C14H18N2O7
분자량
326.3

이름 및 동의어

Dinobuton973-21-7DrawinolAcrexDinofenKasebonSytasolAkrexTalanDESSINIsophen (pesticide)Union Carbide 19786
이름 더 보기
디노부톤디노브톤데신2,4-다이나이트로-6-sec-뷰틸페닐 아이소프로필 카보네이트2-sec-뷰틸-4,6-다이나이트로페닐 아이소프로필 카보네이트다이나이트로-sec-뷰틸페닐 아이소프로필 카보네이트아이소프로필 2,4-다이나이트로-6-sec-뷰틸페닐 카보네이트카본산, 1-메틸에틸 2-(1-메틸프로필)-4,6-다이나이트로페닐 에스터카본산, 2-sec-뷰틸-4,6-다이나이트로페닐 아이소프로필 에스터탄산,1-메틸에틸2-(1-메틸프로필)-4,6-디니트로페닐에스테르탄산,2-sec-부틸-4,6-디니트로페닐이소프로필에스테르CPBAmc1053ds18302oms1056
2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonateDTXSID4040268MC 1053UC 19786OMS 1056A711XEV1PFENT 27,2442,4-Dinitro-6-sec-butylphenyl isopropyl carbonate

데이터베이스 식별자

CAS
62655-72-5、973-21-7
PubChem CID
13783

물성

구조 계산 물성

XLogP
4.3
극성 표면적
127 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
7
회전 가능 결합 수
6
무거운 원자 수
23
형식 전하
0
복잡도
443

실험 및 물리화학적 성질

Pesticides · 3건

Acaricides, Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

Color/Form · 2건

CRYSTALS FROM METHANOL OR PETROLEUM ETHER

PALE YELLOW SOLID

Solubility · 2건

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 · 2건

56-57 °C

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

Vapor Pressure · 2건

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

안전 및 규제

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

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Hazards Summary · 1건

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 · 2건

Dinobuton

Marine pollutant

Hazard Classes and Categories · 3건

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute Tox. 3 *

안전 및 보호

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

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.

화학 및 산업

약리 정보

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 · 5건

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 · 1건

[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

용도 및 제조

Uses · 5건

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.

관련 반응

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
DTXSID
DTXSID4040268
ChEMBL
CHEMBL1358468
ChEBI
CHEBI:81914
UNII
A711XEV1PF
EC Number
213-546-1
Nikkaji
J3.356A

물리화학적 성질

녹는점
61 · 61-62℃
끓는 점
464.35 °C · 464.35°C (rough estimate)
밀도
1.2731 · 1.2731 (rough estimate)
굴절률
1.511 · 1.5110 (estimate)
수용성
물에 불용성
Merck
13 · 13,3315
BRN
2065340 · 2065340
Henry's Law Constant
6.2 · 6.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
EPA
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.

독성 정보

Environmental Fate · 3건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 2건

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 · 1건

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).

안전 데이터

wgk
3
rtecs
FF9100000
ridadr
2779
독성
LD50 in male, female rats (mg/kg): 59, 71 orally (Gaines)
HS 번호
29209090
risk_code
25-50/53
hazard_code
T,N
safety_code
37-45-60-61
포장분류
III
위험 등급
6.1(b)
기존화학 물질
KE-04283
유해 물질 데이터
973-21-7(Hazardous Substances Data)
함량 및 규제정보
물질구분: 유독물질; 혼합물(제품)함량정보: 디노브톤 및 이를 1% 이상 함유한 혼합물
유해화학물질 필터링
97-1-23
Methods of Manufacturing · 2건

...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 · 2건

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%.

응용 분야

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

공급사27 곳

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亚索试剂400-873-6778 18660992876 · [email protected]
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