Dimethipin
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Dimethipin
structure -
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CAS No:
55290-64-7
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Formula:
C6H10O4S2
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Chemical Name:
Dimethipin
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Synonyms:
1,4-Dithiin,2,3-dihydro-5,6-dimethyl-,1,1,4,4-tetraoxide;N 252;2,3-Dihydro-5,6-dimethyl-1,4-dithiine 1,1,4,4-tetroxide;UBI-N 252;Harvade;2,3-Dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide;Tetrathiin (desiccant);Oxidimethiin;Tetrathiin;Dimethipin;Harvade 25F;Harveyd F-25;Harvade F 25
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CAS No:
Description
Dimethipin appears as colorless crystals with a mild odor. Used as a defoliant.
Dimethipin appears as colorless crystals with a mild odor. Used as a defoliant.|Dimethipin is a sulfone.
Dimethipin Basic Attributes
210.27100
210.27
259-572-7
HLV651AHBB
2811
DTXSID0024052
Long white needles from water.|White crystalline solid /TECHNICAL GRADE/
Characteristics
85.04000
2.24260
1.59 g/cm3 @ Temp: 23 °C
167-169 °C
483.6ºC at 760 mmHg
-4ºC
1.514
0.02 M|In acetonitrile 180 g/l, methanol 10.7 g/l, toluene 8.979 g/l (all at 25 °C).|In water, 4.6 g/l at 25 °C.
APPROX -4ºC
3.83e-07 mmHg|3.83X10-7 mm Hg at 25 °C
Mild odor
Henry's Law constant = 2.3X10-6 Pa-cu m/mole at 25 °C
pKa = 10.88
Stable for 1 year at 20 °C; 14 days at 55 °C. Stable to light greater than or equal to 7 days at 25 °C. Undergoes degradation in aqueous solution.|Photolysis rate constants: 9.07X10-3 /day in soil at 25 °C; 0.017 /day in water at 25 °C and pH 5 to 9.|Hydrolysis rate constants: 6.9X10-5 at pH 3; 1.5X10-5 at pH 6; and 7.9X10-4 at pH 9 (all at 25 °C).
Slowly decomposes in water.
Hydrocarbons, Aliphatic Unsaturated
Water-Reactive
DIMETHIPIN slowly decomposes in water to form toxic or flammable products. The decomposition is accelerated by acids. May react with aldehydes, nitrides, and hydrides to generate flammable gases. Reacts with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides.
Safety Information
III
6.1(b)
UN 2811
R11; R36; R66; R67; R22
JO5090000
Stable for 1 yr at 20 °C, 14 days at 55 °C. Stable to light for at least 7 days at 25 °C. Undergoes degradation in aqueous solution.
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.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)
Toxicity
LD50 Rat oral 500 mg/kg|LD50 Rabbit percutaneous >5,000 mg/kg|NOEL Rat 1 mg/kg/day /chronic feeding studies/|NOEL Dog 25 mg/kg/day /chronic feeding studies/|LD50 Rat oral 1,660 mg/kg /Harvade/
Dimethipin's production and use as a defoliant and seed desiccant(1,2) will result in its release to the environment(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), a measured Koc value of 3.3(2), indicates that dimethipin is expected to have very high mobility in soil(SRC). Volatilization of dimethipin from moist soil surfaces is not expected to be important(SRC) given a measured Henry's Law constant of 1.7X10-8 atm-cu m/mole(3). Dimethipin is not expected to volatilize from dry soil surfaces based on its measured vapor pressure(2). The half-life of dimethipin in soil is approximately 104 to 149 days(2). A photolysis half-life of 76 days was calculated for dimethipin in soil(SRC) from a measured rate constant(3,SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), a measured Koc value of 3(2), indicates that dimethipin is not expected to adsorb to suspended solids and sediment in water(SRC). Dimethipin is not expected to volatilize from water surfaces(3,SRC) based on a measured Henry's Law constant of 1.7X10-8 atm-cu m/mole(3). According to a classification scheme(4), an estimated BCF of 0.44(5,SRC), from a measured log Kow of -0.17(2), suggests that bioconcentration in aquatic organisms is low(SRC). A photolysis half-life of 2.0 days was calculated for dimethipin in water at pH 5 to 9(SRC) from a measured rate constant(3). Hydrolysis is not expected to be an important process at environmental pHs(3,SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethipin, which has a measured vapor pressure of 3.8X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dimethipin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be about 3.0 and 3.7 hours, respectively(3,SRC). Particulate-phase dimethipin may be physically removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of dimethipin with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 3.0 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor phase reaction with ozone has been estimated as 7.4X10-17 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 3.7 hours at an average ambient ozone concentration of 7X10+11 molecules/cu cm(1,SRC). Stability of dimethipin to light is greater than or equal to 7 days at 25 °C(2). In aqueous solution, dimethipin is degraded(2); rate and method of degradation were not specified(SRC). The half-life of dimethipin in soil is approximately 104 to 149 days(2); the method of degradation was not specified(SRC). The rate constant for the hydrolysis of dimethipin has been measured to be 1.5X10-5 /day at pH 6 and 25 °C(3). This corresponds to a half-life of about 126 years(3,SRC). Rate constants for the photolysis of dimethipin in both soil and water have been measured to be 9.07X10-3 and 0.017 /day, respectively, at 25 °C(3). These correspond to photolysis half-lives of 76 days in soil and 2.0 days in water at pH 5 to 9(3,SRC).
An estimated BCF of 0.44 was calculated for dimethipin(SRC), using a measured log Kow of -0.17(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF suggests that bioconcentration in aquatic organisms is low(SRC).
3.02 L/kg|A Koc of 3.3 was determined in clay (%organic matter 4.8, pH 5.9)(1,3). According to a recommended classification scheme(2), the measured Koc of dimethipin suggests it is expected to have very high mobility in soil(SRC).
The Henry's Law constant for dimethipin is 1.7X10-8 atm-cu m/mole(1). This value indicates that dimethipin will be essentially nonvolatile from water surfaces(2,SRC). Volatilization from wet and dry soil surfaces is not expected based on dimethipin's measured Henry's Law constant(1) and vapor pressure of 3.8X10-7 mm Hg, respectively(2).
Occupational exposure to dimethipin may occur through inhalation of dust particles and dermal contact with this defoliant/desiccant during or after its application or at workplaces where dimethipin is produced or used. (SRC)
Drug Information
Defoliant and desiccant. Interferes with protein synthesis in plant epidermis.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Carcinogens
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Dimethipin Use and Manufacturing
Acetoin + 1,2-ethanedithiol (sulfide formation/oxidation)
88,000 pounds active ingredient/year in 1989.
Suspension concentrate.
Product analysis by gas liquid chromatography or infrared spectrometry. Residues determined by gas liquid chromatography using a sulfur specific detector.
Agrochemicals -> Herbicides, Plant Growth Regulators|Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:210.3
XLogP3:-0.5
Hydrogen Bond Acceptor Count:4
Exact Mass:210.00205114
Monoisotopic Mass:210.00205114
Topological Polar Surface Area:85
Heavy Atom Count:12
Complexity:371
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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