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Dinoseb ( CASNO:88-85-7 )

Identification and Related Records
Name:
Dinoseb
CAS Registry number:
88-85-7
Synonyms:
Phenol,2-sec-butyl-4,6-dinitro- (6CI,8CI)
2,4-Dinitro-6-(1-methylpropyl)phenol
2,4-Dinitro-6-sec-butylphenol
2-(1-Methylpropyl)-4,6-dinitrophenol
2-sec-Butyl-4,6-dinitrophenol
4,6-Dinitro-2-(1-methyl-n-propyl)phenol
4,6-Dinitro-2-(2-butyl)phenol
4,6-Dinitro-2-sec-butylphenol
4,6-Dinitro-o-sec-butylphenol
6-sec-Butyl-2,4-dinitrophenol
Aatox
BNP 20
BNP 30
Blaartox
Butaphen
Butaphene
Chemox P.E.
DBNF
DN 289
DNBP
DNOSBP
DNSBP
Desicoil
Dibutox
Dibutox 20CE
Dinoseb
Dow General
Dytop
Hivertox
Ladob
Laseb
Liro DNBP
NSC 202753
Premerge
Super Kabrol
WSX 8365
EINECS(EC#):
201-861-7
Molecular Formula:
C10H12 N2 O5
Molecular Weight:
240.2127
Inchi:
InChI=1S/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3
InChIKey:
OWZPCEFYPSAJFR-UHFFFAOYSA-N
Canonical SMILES:
CCC(C)C1=CC(=CC(=C1O)[N+](=O)[O-])[N+](=O)[O-]
Chemical and Physical Properties
Density:
1.29
Melting Point:
55.5℃
Boiling Point:
318.1°C at 760 mmHg
Refractive Index:
1.589
Flash Point:
>100°C
Water:
0.0052 g/100 mL
Solubilities:
0.0052 g/100 mL
Color/Form:
Yellow crystals
Orange solid
Stability:
Stable. Strong oxidizing agent. Incompatible with reducing agents, combustible material.
Storage temp:
2-8°C
Spectral properties:
Index of refraction 1.5707 @ 45 deg C/D
Intense mass spectral peaks: 211 m/z (100%), 163 m/z (40%), 147 m/z (23%), 117 m/z (19%)
Computed Properties:
Molecular Weight:240.21268 [g/mol]
Molecular Formula:C10H12N2O5
XLogP3:3.6
H-Bond Donor:1
H-Bond Acceptor:5
Rotatable Bond Count:2
Tautomer Count:4
Exact Mass:240.074622
MonoIsotopic Mass:240.074622
Topological Polar Surface Area:112
Heavy Atom Count:17
Formal Charge:0
Complexity:298
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:1
Feature 3D Anion Count:2
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:6
Safety and Handling
Hazard Codes:
T:Toxic;N:Dangerousfortheenvironment;
Risk Statements:
R24/25;R44;R50/53;R61;R62
Safety Statements:
S45;S53;S60;S61
HazardClass:
6.1(a)
PackingGroup:
II
Skin, Eye, and Respiratory Irritations:
Staining of skin & minor irritation by very small amt. ... Mild to moderate irritation ... /of eyes/. Inhalation /of/ dusts may be irritating ...
Cleanup Methods:
Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning, or by dissolving them in water, or other solvent in the factory environment.
Transport:
UN 2810
Formulations/Preparations:
EMULSIFIABLE CONCENTRATE, AQUEOUS SOLUTION & OIL SOLUTION.
The cmpd is usually marketed as soluble sodium, ammonium or alkanolamine salts; the acetylated phenol (dinoseb acetate) & the methacrylate ester (dinoseb methacrylate, also known as binapacryl ...) are also available.
Other Preventative Measures:
Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Protective Equipment and Clothing:
Staining of skin & minor irritation by very small amt. ... Mild to moderate irritation ... /of eyes/. Inhalation /of/ dusts may be irritating ...
Disposal Methods:
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P020, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Dinoseb is a good candidate for liquid injection incineration, with a temp range of 650 to 1,600 deg C and a residence time of 0.1 to 2.0 seconds. Also, a good candidate for rotary kiln incineration, with a temp range of 820 to 1,600 deg C with a residence time of seconds. Also, a good candidate for fluidized bed incineration, with a temp range of 450 to 980 deg C and a residence time of seconds.
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
Incineration is suggested at 1000 deg C (2.0 sec minimum) with adequate scrubbing equipment for the removal of NO(x). Recommendable method: Incineration. Not recommendable method: Hydrolysis. Peer-review: Alkaline and acid hydrolysis not recommendable due to toxicity of the reaction products. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

PRODUCED BY NITRATION OF 2-SEC-BUTYLPHENOL, OBTAINED BY THE REACTION OF BUT-2-ENE WITH PHENOL & SEPARATION OF THE 4-ALKYL ISOMER.
BY SULFONATION OF PHENOL TO BLOCK p-POSITION, FOLLOWED BY BUTYLATION & REMOVAL OF SULFONIC GROUP.
REACTION OF O-SEC-BUTYLPHENOL WITH SULFURIC ACID & NITRIC ACID
U.S. Imports

(1977) 1.70X10+7 G (PRINCPL CUSTOMS DISTS)
(1982) 1.14X10+9 G (PRINCPL CUSTOMS DISTS)
U.S. Production

(1978) 3.86X10+9 G (CONSUMPTION-INCL IMPORTS)
(1982) 2.81X10+9 G (CONSUMPTION-INCL IMPORTS)
Consumption Patterns

HERBICIDE FOR SOYBEANS, 32%; VEGETABLES, 23%; DECIDUOUS FRUITS & NUTS, 11%; PEANUTS, 8%; CITRUS, 3%; GRAIN CROPS, 2%; OTHER FIELD CROPS, 6%; INDUSTRIAL/COMMERCIAL USES, 15%. (1982)
Soybeans, 40%; cotton, 15%; potatoes, 16%; peanuts, 9%; alfalfa, 4%; snap beans, 2%; peas, 2%; grapes, 2%; & almonds, 1% (1986; major use sites by volume)
Biomedical Effects and Toxicity
Pharmacological Action:
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
- Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
- Chemicals used to destroy pests of any sort. The concept includes fungicides (FUNGICIDES, INDUSTRIAL); INSECTICIDES; RODENTICIDES; etc.
Biomedical Effects and Toxicity:
... RATS POISONED BY CONSUMPTION, INHALATION, OR SKIN EXPOSURE TO HERBICIDES DINITROISOPROPYL-(DNPP) AND DINITROBUTYLPHENOL (DNBP) ... LIVER, KIDNEY, SPLEEN AND BLOOD CONTAINED METABOLITES.
FOLIAR ABSORPTION CHARACTERISTICS: PRINCIPALLY DIRECT CONTACT EFFECT. ... NO TRUE TRANSLOCATION. NO RESIDUES HAVE BEEN TRACED TO FOLIAR OR ROOT UPTAKE.
DISPOSITION OF (14)C-DINOSEB WAS DETERMINED IN NONPREGNANT MICE EXPOSED TO TEMP OF 0, 24, & 32 DEG C. THE /TIME/ PERIOD OF ENVIRONMENTAL TEMP STUDIED (3-24 HR) HAD NO EFFECT ON THE RATE OF DISAPPEARANCE OF DINOSEB FROM PLASMA OR OTHER TISSUES EXAMINED. [PREACHE MM; TERATOLOGY 12: 147-56 (1975)] PubMed Abstract
AFTER ORAL OR IP ADMIN TO PREGNANT MICE DINOSEB WAS FOUND IN ALL MATERNAL TISSUES & WAS SHOWN TO CROSS THE PLACENTA. RATE OF ABSORPTION WAS 40 TIMES GREATER AFTER IP THAN ORAL ADMIN. DINOSEB WAS EXCRETED IN URINE & FECES, & METABOLITES WERE FOUND IN MATERNAL LIVER & KIDNEY & IN THE EMBRYO. [GIBSON JE, RAO KS; FOOD COSMET TOXICOL 11 (1): 45-52 (1973)] PubMed Abstract
FOOD DEPRIVATION FOR 24 HR SLOWED & PHENOBARBITAL HASTENED DISAPPEARANCE OF DINOSEB FROM PLASMA. FOOD DEPRIVATION FOR 48 HR & SKF-525A PRETREATMENT DID NOT AFFECT DISAPPEARANCE FROM PLASMA, BUT THEY, RESPECTIVELY, INCR & DECR RATE OF DISAPPEARANCE FROM LIVER. [PREACHE MM, GIBSON JE; J TOXICOL ENVIRON HEALTH 1 (1): 107-18 (1975)] PubMed Abstract
MOST NITROPHENOLS ... ARE WELL ABSORBED FROM THE GI TRACT, ACROSS THE SKIN, & BY THE LUNG WHEN VERY FINE DROPLETS ARE INHALED. /NITROPHENOLS/
... The phenolic pesticides appear to be readily assimilated by animals but excreted slowly over a period of many weeks. /Phenolic pesticides/
AFTER ORAL OR IP ADMINISTRATION OF DINOSEB ... TO PREGNANT MICE, THE PARENT CMPD & METABOLITES WERE FOUND @ LOW CONCN IN EMBRYOS. INITIAL LEVELS IN EMBRYOS AFTER IP ADMINISTRATION WERE HIGHER THAN THOSE FOUND AFTER ORAL DOSING, WHICH MIGHT EXPLAIN ... DIFFERENT TERATOGENIC RESPONSE ELICITED BY ORAL (NEG) & IP (POS) ROUTES.
Acrex and its metabolite dinoseb showed reversible binding with human serum albumin. Spectrofluorometry showed that the pesticides caused conformational changes in the protein. Luminescence study indicated albumin to possess 2 high affinity receptors. Equilibrical dialysis suggests the binding of acrex and dinoseb with serum albumin to be low affinity and high capacity type. The numbers of centers for acrex and dinoseb on the albumin are 18 and 12, respectively.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: WATER-SOLUBLE SALTS OF DINOSEB ... LEACH READILY IN SOIL. HOWEVER, OIL-SOLUBLE OR WATER-MISCIBLE FORMULATIONS OF DINOSEB MOVED MUCH LESS THAN WATER-SOLUBLE FORMULATIONS.
TERRESTRIAL FATE: Dinoseb is expected to biodegrade in slowly soil. It should bind weakly to soil. Therefore, leaching in soil is possible and dinoseb has been detected in groundwater. However, it may bind more strongly to clay soils, specialy at acidic pH. Photolytic degrdration of dinoseb from soil surface may be important. Volatilization is not expected to be significant. In the absence of volatilization, the half-life of dinoseb in the vadose zone sandy loam soil was estimated to be about 100 days(1).
AQUATIC FATE: Dinoseb may photodegrade in surface water with a half-life of 14-16 days(1). Hydrolysis in water may not be important(1). Volatilization and adsorption to sediments are not expected to be significant. It is unlikely to undergo significant biodegradation in most natural waters(SRC).
ATMOSPHERIC FATE: Based on its vapor pressure of 8.5X10-2 mm Hg at 20 deg C(1), dinoseb may exist entirely in the vapor phase in the atmosphere(2). The half-life for the reaction of vapor phase dinoseb with photochemically generated hydroxyl radicals in the atmosphere was estimated to be 4.1 days(3). Due to its water solubility of 52 mg/L at 25 deg C(4), some of the atmospheric dinoseb may be removed by wet deposition.
RESULTANT AVERAGE PERSISTENCE OF PHYTOTOXICITY @ RECOMMENDED RATES: 2 TO 4 WK UNDER AVERAGE CONDITIONS OF USE.
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