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Dimethipin

HCID 41385
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
55290-64-7
Standard SMILES
CC1=C(C)S(=O)(=O)CCS1(=O)=O
InChIKey
PHVNLLCAQHGNKU-UHFFFAOYSA-N
Molecular formula
C6H10O4S2
Average molar mass
210.3 g/mol
Monoisotopic mass
210.00205114

Overview

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

Names & identifiers

Preferred name
Dimethipin
IUPAC
5,6-dimethyl-2,3-dihydro-1,4-dithiine 1,1,4,4-tetraoxide
English name
DIMETHIPIN
Molecular formula
C6H10O4S2
Molecular weight
210.27

Names & synonyms

DIMETHIPIN55290-64-7Caswell No. 472AAHarvade-5FDimethipin [ISO]Dimethipin [ANSI:BSI:ISO]UNI-N252DTXSID0024052HSDB 6615UNII-HLV651AHBBHLV651AHBBEINECS 259-572-7
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
-0.5
Topological polar surface area
85 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
371

Experimental & physicochemical properties

Chemical ClassesCarcinogens
Pesticides · 5 items

Pesticide -> EPA IRIS

Herbicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide (Dimethipin) -> USDA PDB

LogP · 2 items

Log Kow = -0.17

-0.17

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

Long white needles from water.

White crystalline solid /TECHNICAL GRADE/

Solubility · 2 items

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 items

0.00000038 [mmHg]

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 · 4 items

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.

Hazard information

Regulatory Information · 4 items

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 items

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.

Chemistry & industry

Pharmacology

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

Uses & manufacturing

Uses · 5 items

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.
Applications · 4 items

DescriptionDimethipin is a plant growth regulator and defoliant. It is highly soluble in water and has a low volatility. Depending on local conditions it may be persistent in both soil and water systems. It also has potential to leach to groundwater. Dimethipin is moderately toxic to aquatic species (except algae), birds, earthworms and honeybees. This substance also has a moderate oral mammalian toxicity, is an irritant and skin sensitizer. There is also the suggestion that it is a carcinogen.

UsesPlant growth regulator.

UsesDimethipin 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.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
EC Number
259-572-7

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 items

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.

Physicochemical properties

Melting point
167 · 167-169℃
Boiling point
319.8 °C · 319.8°C (rough estimate)
Density
1.59 g/cm3 · 1.59 g/cm3 (23℃)
refractive index
1.522 · 1.5220 (estimate)
Flash point
-4 °C · -4 °C
storage temp.
-4 °C · APPROX -4°C
form
solid
Henry's Law Constant
4.3 · 4.3×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
FDA UNII
651 AHBB · HLV651AHBB
Pesticides Freedom of Information Act (FOIA)
Harvade
EPA Substance Registry System
Dimethipin (55290-64-7)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
Hazard Codes
F,Xi,Xn
Risk Statements
11 · 11-36-66-67-22
Safety Statements
16 · 16-26-33
RIDADR
2811 · 2811
RTECS
5090000 · JO5090000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
55290 · 55290-64-7(Hazardous Substances Data)

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 item

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 items

Acute Tox. 4 (100%)

Carcinogens

Safety & protection

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 item

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 items

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)]:

Toxicology

Target OrgansHepatic
Ecotoxicity Values · 5 items

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 items

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 items

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 item

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 item

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 items

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 item

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).

Regulatory information

FIFRA Requirements · 2 items

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.

Safety data

rtecs
JO5090000
ridadr
2811
risk_code
11-36-66-67-22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
F,Xi,Xn
safety_code
16-26-33
hazard_class
6.1(b)
packing_group
III
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501
Hazardous Substances Data
55290-64-7(Hazardous Substances Data)

General DescriptionColorless crystals with a mild odor. Used as a defoliant.

Suppliers24 total

安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
成都梓永智研生物科技有限公司17780686372 · [email protected]
上海艾梯西生物科技有限公司18721763493 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
南京罗迈美生物科技有限公司[email protected]
常州阿桑奇科技有限公司18961267976 · [email protected]
深圳市丽晶生化科技有限公司0755-85201366 18938635012 · [email protected]
北京坛墨质检科技有限公司010-52889049 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
南京枫景晴生物科技有限公司15062262630 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
陕西缔都医药化工有限公司+86-29-87569266 +86-17392581500 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
亚索试剂400-873-6778 18660992876 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]

Additional notes

DefinitionChEBI: Dimethipin is a sulfone.