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Home > Encyclopedia > 2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate

2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate

2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate structure

2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate 

structure
  • CAS No:

    973-21-7

  • Formula:

    C14H18N2O7

  • Chemical Name:

    2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate

  • Synonyms:

    Carbonic acid,1-methylethyl 2-(1-methylpropyl)-4,6-dinitrophenyl ester;Carbonic acid,2-sec-butyl-4,6-dinitrophenyl isopropyl ester;2,4-Dinitro-6-sec-butylphenyl-isopropylcarbonate;Dinobuton;Isopropyl 2,4-dinitro-6-sec-butylphenyl carbonate;UC 19786;Union Carbide 19786;Dessin;Kasebon;2,4-Dinitro-6-sec-butylphenyl-O-isopropyl carbonate;Acrex;MC 1053;2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate;Drawinol;Isophen;Isophen (pesticide);Akrex;61840-20-8;1135443-32-1

  • Categories:

    Agrochemicals  >  Insecticides

Description

Dinobuton is a C-nitro compound.

2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate Basic Attributes

326.3

326.30

213-546-1

DTXSID4040268

CRYSTALS FROM METHANOL OR PETROLEUM ETHER|PALE YELLOW SOLID

2920909090

Characteristics

127

4.98670

1.269 g/cm3

56-57 °C

419.9ºC at 760 mmHg

163.2ºC

1.556

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

FORMULATION SHOULD NOT BE STORED BELOW ZERO.

Less than 10-5 mbar at 20 deg C

Oral-Rat  LD50: 59 mg/kg; Oral-Mouse LD50: 170 mg/kg

Combustion produces toxic nitrogen oxide gas

HYDROLYZED BY ALKALI TO PARENT PHENOL DINOSEB

Non-corrosive

Safety Information

III

6.1(b)

2779

3

25-50/53

37-45-60-61

FF9100000

T,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

P273-P301 + P310-P501

H301-H410

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.|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.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P301+P310, P321, P330, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 194 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

GLOVES & RESPIRATOR FILTER.

Toxicity

highly toxic

Dessin's use as a non-systemic acaricide, fungicide(1), and miticide(2) will result in its direct release to the environment(SRC).

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).

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).

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).

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).

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).

During 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).

Drug Information

[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

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.

PESTICIDES AT 0.1 TO 0.01 MEAN LC50 AFFECTED PEROXIDASE ACTIVITY IN SCALY CARP YEARLINGS. ACREX CAUSED BIPHASIC RESPONSE (STIMULATION & NORMALIZATION).

Treatment of poisoning ... is largely non-specific. Sedatives must be used with care ... In man, respiratory stress is greatly relieved by the administration of oxygen. /Dinitro compounds/|VET: The animal should be kept in as cool an environment as possible, sedatives (barbiturates) may be given to keep it quiet and water and/or glucose saline may be used .. to combat dehydration due to sweating. /Dinitro compounds/

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.

Acrex

2-sec-Butyl-4,6-dinitrophenyl isopropyl carbonate Use and Manufacturing

Methods of Manufacturing

...BY CONDENSATION OF ALKALI SALT OF DINOSEB WITH ISOPROPYL CHLOROFORMATE.|Production is by esterification of 2-sec-butyl-4,6-dinitrophenol with isopropyl chloroformate.

Uses

Miticide.

WETTABLE PRODUCTS 50%; AQ SUSPENSION 50%; ATOMIZING CONCENTRATES; EMULSIFIABLE CONCENTRATES 30%.

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%.

...RESIDUE ANALYSIS IS BY CHROMATOGRAPHY ON ALUMINA COLUMN & COLORIMETRIC MEASUREMENT OF THE RESULTING DINOSEB AT 378 NM.|SPECTROPHOTOMETRIC METHOD IS DESCRIBED FOR THE DETECTION OF THE ACTIVE-INGREDIENT CONTENT OF TECHNICAL & FORMULATED DNOC & DINOSEB & TECHNICAL DINOBUTON.|Analysis of products: Esterification, with formation of dinoseb, and determination as for the latter: reduction of the nitro group to an amino group with excess titanium chloride solution and back-titration with ferric ammonium sulphate solution.|Extraction with hexane, transfer into benzene, formation of dinoseb by cleavage of ester during column chromatography on aluminium oxide, and determination of the dinoseb as the butylamine salt by spectrophotometry. Determination by gas chromatography after saponification and methylation of the phenol with diazomethane.

Agrochemicals -> Acaricides, Fungicides|ACARICIDES

Computed Properties

Molecular Weight:326.30
XLogP3:4.3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:6
Exact Mass:326.11140092
Monoisotopic Mass:326.11140092
Topological Polar Surface Area:127
Heavy Atom Count:23
Complexity:443
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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