HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.9
  1. Home
  2. /Compound

Dinobuton

HCID 13783
New noteNew reactionRequest quotesPrint preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
62655-72-5
Standard SMILES
CCC(C)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)OC(C)C
InChIKey
HDWLUGYOLUHEMN-UHFFFAOYSA-N
Molecular formula
C14H18N2O7
Average molar mass
326.3 g/mol
Monoisotopic mass
326.11140092

Overview

Dinobuton is a C-nitro compound.

Names & identifiers

Preferred name
Dinobuton
IUPAC
(2-butan-2-yl-4,6-dinitrophenyl) propan-2-yl carbonate
English name
DINOBUTON
Molecular formula
C14H18N2O7
Molecular weight
326.3

Names & synonyms

Dinobuton973-21-7DrawinolAcrexDinofenKasebonSytasolAkrexTalanDESSINIsophen (pesticide)Union Carbide 19786
Show more names
CPBAmc1053ds18302oms1056
2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonateDTXSID4040268MC 1053UC 19786OMS 1056A711XEV1PFENT 27,2442,4-Dinitro-6-sec-butylphenyl isopropyl carbonate

Database identifiers

CAS
62655-72-5、973-21-7
PubChem CID
13783
DTXSID
DTXSID4040268
ChEMBL
CHEMBL1358468
ChEBI
CHEBI:81914
UNII
A711XEV1PF
EC Number
213-546-1
Nikkaji
J3.356A

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
127 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
6
Heavy atoms
23
Formal charge
0
Complexity
443

Experimental & physicochemical properties

Pesticides · 3 items

Acaricides, Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

Color/Form · 2 items

CRYSTALS FROM METHANOL OR PETROLEUM ETHER

PALE YELLOW SOLID

Solubility · 2 items

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 items

56-57 °C

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

Vapor Pressure · 2 items

0.0000011 [mmHg]

Less than 10-5 mbar at 20 °C

Physical DescriptionPale yellow solid; [HSDB] Yellowish crystalline solid; [MSDSonline]
Other Experimental Properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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)

Hazard information

Hazards Summary · 1 item

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 items

Dinobuton

Marine pollutant

Hazard Classes and Categories · 3 items

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute Tox. 3 *

Safety & protection

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

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.

Chemistry & industry

Pharmacology

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 items

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 item

[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

Uses & manufacturing

Uses · 5 items

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.

Suppliers

Loading…

Open inquiries

Loading…

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
HYDROLYZED BY ALKALI TO PARENT PHENOL DINOSEB

Physicochemical properties

Melting point
61 · 61-62℃
Boiling point
464.35 °C · 464.35°C (rough estimate)
Density
1.2731 · 1.2731 (rough estimate)
refractive index
1.511 · 1.5110 (estimate)
Water Solubility
Insoluble in water
Merck
13 · 13,3315
BRN
2065340 · 2065340
Henry's Law Constant
6.2 · 6.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
CAS DataBase Reference
973 · 973-21-7
EWG's Food Scores
1 · 1
FDA UNII
711 XEV1PF · A711XEV1PF
EPA Substance Registry System
Dinobuton (973-21-7)
Symbol(GHS)
6 · GHS06,GHS09
Signal word
Danger
Hazard statements
301 · H301-H330-H410
Precautionary statements
260 · P260-P264-P270-P271-P273-P304+P340+P310
Hazard Codes
T,N
Risk Statements
25 · 25-50/53
Safety Statements
37 · 37-45-60-61
RIDADR
2779 · 2779
WGK Germany
3 · 3
RTECS
9100000 · FF9100000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29209090 · 29209090
Hazardous Substances Data
973 · 973-21-7(Hazardous Substances Data)
Toxicity
50 in · LD50 in male, female rats (mg/kg): 59, 71 orally (Gaines)

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.

Toxicology

Environmental Fate · 3 items

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 item

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 item

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 item

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 item

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 item

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 items

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 item

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).

Safety data

wgk
3
rtecs
FF9100000
ridadr
2779
hs_code
29209090
Toxicity
LD50 in male, female rats (mg/kg): 59, 71 orally (Gaines)
risk_code
25-50/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_code
T,N
safety_code
37-45-60-61
hazard_class
6.1(b)
packing_group
III
Hazard statements
H301-H330-H410
Precautionary statements
P260-P264-P270-P271-P273-P304+P340+P310
Hazardous Substances Data
973-21-7(Hazardous Substances Data)
Methods of Manufacturing · 2 items

...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 items

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%.

Applications · 3 items

DescriptionDinobuton is a dinitrophenol multi-use pesticide which is not approved for use in the UK nor the EU. It has a low aqueous solubility but soluble in most organic solvents. Limited information is available regarding its environmental fate but is reported as being non-mobile. It is moderately toxic to mammals, birds and bees but considered highly toxic to fish. Limited data is available on its toxicity to humans but some reports suggest it is a possible cardiovascular, liver and kidney toxicant

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

UsesMiticide.

Additional notes

DefinitionChEBI: Dinobuton is a C-nitro compound.