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2,3-ジヒドロ-5,6-ジメチル-1,4-ジチイン1,1,4,4-テトラオキシド

Dimethipin

HCID 41385
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
55290-64-7
標準SMILES
CC1=C(C)S(=O)(=O)CCS1(=O)=O
InChIKey
PHVNLLCAQHGNKU-UHFFFAOYSA-N
分子式
C6H10O4S2
平均分子量
210.3 g/mol
単同位体質量
210.00205114

概要

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

名称と識別子

優先名称
Dimethipin
IUPAC
5,6-dimethyl-2,3-dihydro-1,4-dithiine 1,1,4,4-tetraoxide
現地名
2,3-ジヒドロ-5,6-ジメチル-1,4-ジチイン1,1,4,4-テトラオキシド
英語名
DIMETHIPIN
分子式
C6H10O4S2
分子量
210.27

名称と別名

DIMETHIPIN55290-64-7Caswell No. 472AAHarvade-5FDimethipin [ISO]Dimethipin [ANSI:BSI:ISO]UNI-N252DTXSID0024052HSDB 6615UNII-HLV651AHBBHLV651AHBBEINECS 259-572-7
名称をさらに表示
2,3-ジヒドロ-5,6-ジメチル-1,4-ジチイン1,1,4,4-テトラオキシドハーバド5,6-ジヒドロ-2,3-ジメチル-1,4-ジチイン1,1,4,4-テトラオキシドジメチピンジメチピン標準品ジメチピン STANDARDジメチピン Standard, 100 µg/mL in MeOH2,3-ジメチル-5,6-ジヒドロ-1,4-ジチイン-1,1,4,4-テトラオキシド5,6-ジメチル-1,2,3,4-テトラヒドロ-1,4-ジチイン-1,1,4,4-テトライウム-1,1,4,4-テトラキス(オラート)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

物性

構造計算による物性

XLogP
-0.5
極性表面積
85 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
0
重原子数
12
形式電荷
0
複雑度
371

実験および物理化学的性質

Chemical ClassesCarcinogens
Pesticides · 5 件

Pesticide -> EPA IRIS

Herbicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide (Dimethipin) -> USDA PDB

LogP · 2 件

Log Kow = -0.17

-0.17

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

Long white needles from water.

White crystalline solid /TECHNICAL GRADE/

Solubility · 2 件

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 件

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

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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.

化学と産業

薬理情報

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

用途と製造

Uses · 5 件

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.
応用分野 · 2 件

使用Dimethipin 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.

一般的な説明Colorless crystals with a mild odor. Used as a defoliant.

サプライヤー24 社

安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
55290-64-7
PubChem CID
41385
DTXSID
DTXSID0024052
ChEMBL
CHEMBL3183474
ChEBI
CHEBI:81912
UNII
HLV651AHBB
EC Number
259-572-7
Physical Description · 2 件

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.

物理化学的性質

融点
167 · 167-169℃
沸点
319.8 °C · 319.8°C (rough estimate)
比重(密度)
1.59 g/cm3 · 1.59 g/cm3 (23℃)
屈折率
1.522 · 1.5220 (estimate)
闪点
-4 °C · -4 °C
貯蔵温度
-4 °C · APPROX -4°C
外見
個体
Henry's Law Constant
4.3 · 4.3×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
EPAの化学物質情報
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 件

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 件

Acute Tox. 4 (100%)

Carcinogens

安全と保護具

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 件

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 件

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)]:

毒性情報

Target OrgansHepatic
Ecotoxicity Values · 5 件

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 件

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 件

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 件

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 件

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 件

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 件

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).

法規制情報

FIFRA Requirements · 2 件

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.

安全データ

rtecs
JO5090000
ridadr
2811
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
有毒物質データの
55290-64-7(Hazardous Substances Data)
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