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Dimethipin

HCID 41385
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Grundinformationen

CAS
55290-64-7
Standard-SMILES
CC1=C(C)S(=O)(=O)CCS1(=O)=O
InChIKey
PHVNLLCAQHGNKU-UHFFFAOYSA-N
Summenformel
C6H10O4S2
Durchschnittliche Molmasse
210,3 g/mol
Monoisotopische Masse
210,00205114

Überblick

Dimethipin appears as colorless crystals with a mild odor. Used as a defoliant.

Namen und Bezeichner

Bevorzugter Name
Dimethipin
IUPAC
5,6-dimethyl-2,3-dihydro-1,4-dithiine 1,1,4,4-tetraoxide
Englischer Name
DIMETHIPIN
Summenformel
C6H10O4S2
Molmasse
210.27

Namen und Synonyme

DIMETHIPIN55290-64-7Caswell No. 472AAHarvade-5FDimethipin [ISO]Dimethipin [ANSI:BSI:ISO]UNI-N252DTXSID0024052HSDB 6615UNII-HLV651AHBBHLV651AHBBEINECS 259-572-7
Weitere Namen anzeigen
n252HARVADEUBI-N 252imethipinHARVADE(R)harvade25ftetrathiinharvadef-25OXYDIMETHIN
EPA Pesticide Chemical Code 1189012,3-Dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetraoxideDIMETHIPIN [HSDB]DTXCID704052UBI-N2522,3-Dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxideDimethipin (ANSI:BSI:ISO)2,3-Dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide

Datenbank-Bezeichner

CAS
55290-64-7
PubChem CID
41385
DTXSID
DTXSID0024052
ChEMBL
CHEMBL3183474
ChEBI
CHEBI:81912
UNII
HLV651AHBB

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,5
Polarare Oberfläche (TPSA)
85 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
0
Schwere Atome
12
Formalladung
0
Komplexität
371

Experimentelle und physikochemische Eigenschaften

Chemical ClassesCarcinogens
Pesticides · 5 Einträge

Pesticide -> EPA IRIS

Herbicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide (Dimethipin) -> USDA PDB

LogP · 2 Einträge

Log Kow = -0.17

-0.17

OdorMild odor
Density1.59 g/cu cm at 23 °C
Color/Form · 2 Einträge

Long white needles from water.

White crystalline solid /TECHNICAL GRADE/

Solubility · 2 Einträge

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.

Melting Point167 to 169 °C
Vapor Pressure · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Regulation (EC) No 1107/2009 (amended)

Dimethipin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2007/553

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,4-Dithiin, 2,3-dihydro-5,6-dimethyl-, 1,1,4,4-tetraoxide: Environment tier I assessment
DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards SummaryMay cause irritation; [MSDSonline]
Reactive GroupHydrocarbons, Aliphatic Unsaturated
FIFRA Requirements · 2 Einträge

Tolerances are established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following raw agricultural commodities: cottonseed; cattle, fat; cattle, meat; cattle, mbyp; goats, fat; goats, meat; goats, mbyp; hogs, fat; hogs, meat; hogs, mbyp; horses, fat; horses, meat; horses mbyp; sheep, fat; sheep, meat; and sheep, mbyp.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of ActionDefoliant and desiccant. Interferes with protein synthesis in plant epidermis.

Verwendung und Herstellung

Uses · 5 Einträge

Used as plant growth regulator, defoliant (cotton, nursery stock, rubber trees, dry beans, and vines), and desiccant (seed harvest of maize, rice, oilseed rape, flax, canola, and sunflowers); [HSDB] Registered as a cotton growth regulator and herbicide for weeds in nursery stock except apples; [Reference #1]

Farming (Pesticides) [Category: Industry]

Plant growth regulator.

Defoliation of cotton, nursery stock, rubber trees, and vines. Potato haulm desiccant. Reduces seed moisture content at harvest of maize, rice, oilseed rape, flax and sunflowers.

Defoliates dry beans; used as a desiccant for seed of canola.

U.S. Production88,000 pounds active ingredient/year in 1989.
Methods of ManufacturingAcetoin + 1,2-ethanedithiol (sulfide formation/oxidation)
Formulations/PreparationsSuspension concentrate.
Anwendungen · 1 Eintrag

VerwendenDimethipin is a defoliation herbicide (1,2) which is found in pesticide formulations for protection of crops. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

Anbieter24 Anbieter

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EC Number
259-572-7

0.00000038 [mmHg]

3.83X10-7 mm Hg at 25 °C

Henry's Law ConstantHenry's Law constant = 2.3X10-6 Pa-cu m/mole at 25 °C
Physical Description · 2 Einträge

Dimethipin appears as colorless crystals with a mild odor. Used as a defoliant.

White solid; [Merck Index] Colorless solid; [CAMEO] White crystalline solid; [MSDSonline]

Stability/Shelf LifeStable 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.

Physikochemische Eigenschaften

Schmelzpunkt
167 · 167-169℃
Siedepunkt
319.8 °C · 319.8°C (rough estimate)
Dichte
1.59 g/cm3 · 1.59 g/cm3 (23℃)
Brechungsindex
1.522 · 1.5220 (estimate)
Flammpunkt
-4 °C · -4 °C
storage temp.
-4 °C · APPROX -4°C
Aggregatzustand
solid
Henry's Law Constant
4.3 · 4.3×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
EPA chemische Informationen
Dimethipin (55290-64-7)

A tolerances is established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following processed feeds when present therein as a result of application of the harvest growth regulant to the growing crops: cottonseed hulls.

Reactivity AlertsWater-Reactive
Reactivity Profile · 1 Eintrag

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.

Air and Water ReactionsSlowly decomposes in water.
Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (100%)

Carcinogens

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Disposal Methods · 1 Eintrag

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.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Allowable Tolerances · 2 Einträge

Tolerances are established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following raw agricultural commodities: cottonseed 0.5 ppm; cattle, fat 0.02 ppm; cattle, meat 0.02 ppm; cattle, mbyp 0.02 ppm; goats, fat 0.02 ppm; goats, meat 0.02 ppm; goats, mbyp 0.02 ppm; hogs, fat 0.02 ppm; hogs, meat 0.02 ppm; hogs, mbyp 0.02 ppm; horses, fat 0.02 ppm; horses, meat 0.02 ppm; horses mbyp 0.02 ppm; sheep, fat 0.02 ppm; sheep, meat 0.02 ppm; and sheep, mbyp 0.02 ppm.

A tolerances is established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following processed feeds when present therein as a result of application fo the harvest growth regulant to the growing crops: cottonseed hulls 0.7 ppm.

Personal Protective Equipment (PPE)Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Toxikologische Informationen

Target OrgansHepatic
Ecotoxicity Values · 5 Einträge

LC50 Mallard duck >5,000 ppm /8-day dietary/

LC50 Bobwhite quail >5,000 ppm /8-day dietary/

LC50 Rainbow trout 52.8 mg/L/96 hr /conditions of bioassay not specified/

LC50 Bluegill sunfish = 20.9 mg/L/96 hr /conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for DIMETHIPIN (6 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

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).

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.
EPA IRIS Information · 3 Einträge

Dimethipin

Hepatic

2 x 10 ^-2 mg/kg-day

Soil Adsorption/MobilityA 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).
Artificial Pollution SourcesDimethipin's production and use as a defoliant and seed desiccant(1,2) will result in its release to the environment(SRC).
Environmental Bioconcentration · 1 Eintrag

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).

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity ExcerptsExtreme eye irritant, not a dermal irritant (rabbits). Weak sensitizer (guinea pigs).
Evidence for Carcinogenicity · 2 Einträge

Cancer Classification: Group C Possible Human Carcinogen

CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Classification is based on an elevated combined incidence of pulmonary adenomas/carcinomas in male, but not in female, CD-1 mice. A rat study is undergoing further evaluation. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.

Environmental Abiotic Degradation · 1 Eintrag

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).

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

Tolerances are established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following raw agricultural commodities: cottonseed; cattle, fat; cattle, meat; cattle, mbyp; goats, fat; goats, meat; goats, mbyp; hogs, fat; hogs, meat; hogs, mbyp; horses, fat; horses, meat; horses mbyp; sheep, fat; sheep, meat; and sheep, mbyp.

A tolerances is established for residues for the harvest growth regulant dimethipin (2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide) ... in or on the following processed feeds when present therein as a result of application of the harvest growth regulant to the growing crops: cottonseed hulls.

Sicherheitsdaten

ridadr
2811
RTECS-Nr.
JO5090000
risk_code
11-36-66-67-22
hazard_code
F,Xi,Xn
safety_code
16-26-33
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
55290-64-7(Hazardous Substances Data)
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