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Dimethrin

HCID 6265
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
70-38-2
Standard SMILES
CC(C)=CC1C(C(=O)OCc2ccc(C)cc2C)C1(C)C
InChIKey
FHNKBSDJERHDHZ-UHFFFAOYSA-N
Molecular formula
C19H26O2
Average molar mass
286.4 g/mol
Monoisotopic mass
286.19328007

Overview

structure

Names & identifiers

Preferred name
Dimethrin
IUPAC
(2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
English name
Dimethrin.
Molecular formula
C19H26O2
Molecular weight
286.41

Names & synonyms

DIMETHRINDimetrin70-38-2DimethrineCaswell No. 359SRP5SEK6S12,4-Dimethylbenzyl chrysanthemumateSHA 034101AI3-21170NSC-15731Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (2,4-dimethylphenyl)methyl ester2,4-Dimethylbenzyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
Show more names
NSC15731NSC 15731Dimethrin.2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2,4-dimethylbenzyl2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2,4-dimethylbenzyl ester2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (2,4-dimethylbenzyl) ester(2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopr opane-1-carboxylateCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (2,4-dimethylphenyl)methyl ester
(2,4-Dimethylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid 2,4-dimethylbenzyl esterCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, 2,4-dimethylbenzyl esterDTXSID8040305(2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylateRefChem:134198DTXCID6020305ENT-21170

Properties

Computed structural properties

XLogP
6.2
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
21
Formal charge
0
Complexity
417

Experimental & physicochemical properties

PesticidesPesticides -> Pyrethrins/Pyrethroids
LogP4.5
Density0.986 @ 20 °C
Color/FormAmber liquid
Solubility · 2 items

Soluble in petroleum hydrocarbons, aromatic petroleum derivatives, alcohols, and methylene chloride.

Insoluble in water.

Boiling Point175 °C @ 3.8 mm Hg
Vapor Pressure0.0000172 [mmHg]
Physical DescriptionAmber liquid; [Hawley]
Other Experimental PropertiesDecomposes by strong alkali

Physicochemical properties

Melting point

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards SummaryRats given by gavage 7 mg/kg/day for 3 weeks had no adverse effects; [HSDB] See Pyrethrum.
State Drinking Water Guidelines(ME) MAINE 2100 ug/l
Federal Drinking Water GuidelinesEPA 2000 ug/l

Safety & protection

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.

Preventive Measures · 5 items

Skin that becomes contaminated with /pyrethrum/ should be promptly washed or showered with soap or mild detergent and water. /Pyrethrum/

Clothing contaminated with /pyrethrum/ should be placed in closed containers for storage until provision is made for the removal of /pyrethrum/ from the clothing. /Pyrethrum/

Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail or need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. /Pyrethrum/

Employees who handle /pyrethrum/ ... should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Pyrethrum/

For more Preventive Measures (Complete) data for DIMETHRIN (9 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 5 items

Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

... Dimethrin (5 mg/kg), administered by intubation to rabbits, is metabolized (by reduction) and excreted in the urine as chrysanthemumic acid and the glucuronic ester of 2,4-dimethyl benzoic acid.

The low toxicity of pyrethroids in mammals is due largely to their rapid biotransformation by ester hydrolysis and/or hydroxylation. /Pyrethroids/

Absorption, Distribution and Excretion... Four rabbits were given 5 ml/kg of undiluted dimethrin by intubation. Urine was collected every 24 hr over a 72 hr period. Identification of two possible metabolites in the urine indicated that dimethrin was absorbed.

Uses & manufacturing

Uses · 4 items

Used as insecticide for mosquito larva in ponds and swamps; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

For Dimethrin (USEPA/OPP Pesticide Code: 034101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticide for use in ponds and swamps as a mosquito larvicide. /Former/

Formulations/PreparationsUSEPA/OPP Pesticide Code 034101; Trade Names: ENT 21,170.
Use ClassificationINSECTICIDES
General Manufacturing Information · 2 items

Discontinued by McLaughlin Gormley King

Synthetic compound produced to duplicate or improve more or less successfully on the biological activity of the pyrethrum plant.

Applications · 2 items

Dimethrin is a pyrethroid ester insecticide mainly used for public health applications. It is largely considered obsolete. It has a low aqueous solubility, low volatility and not considered to be highly mobile. It is toxic to fish. Dimethrin is not particularly toxic to mammals via the oral route and is a recognised irritant.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
70-38-2
PubChem CID
6265
DTXSID
DTXSID8040305
UNII
SRP5SEK6S1
Nikkaji
J4.876C
25 °C · <25 °C
Boiling point
175 °C · 175 °C(Press: 3.8 Torr)
Density
0.986 g/cm3 · 0.986 g/cm3
storage temp.
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Oil
color
Colourless
Henry's Law Constant
1.3 · 1.3×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
FDA UNII
5 SEK6S1 · SRP5SEK6S1
EPA Substance Registry System
Dimethrin (70-38-2)
RIDADR
3082 · 3082
HazardClass
9 · 9
PackingGroup
III
Hazardous Substances Data
70 · 70-38-2(Hazardous Substances Data)

Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/

Wear appropriate equipment to prevent: Repeated or prolonged skin contact. /Pyrethrum and pyrethrins/

Wear eye protection to prevent: Reasonable probability of eye contact. /Pyrethrins/

For more Personal Protective Equipment (PPE) (Complete) data for DIMETHRIN (10 total), please visit the HSDB record page.

Toxicology

Ecotoxicity Values · 4 items

LC50 Perca flavescens 28 ug/l/96 hr. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.

LC50 Lepomis macrochirus 38 ug/l/96 hr. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.

LC50 Ictalurus punctatus 1,140 ug/l/96 hr. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.

LC50 Pimephales promelas 62 ug/l/96 hr; flow through toxicity test.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 31,000(SRC), determined from a structure estimation method(2), indicates that dimethrin is expected to be immobile in soil(SRC). Volatilization of dimethrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Dimethrin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-5 mm Hg(SRC), determined from a fragment constant method(4). Although biodegradation data for dimethrin are not available, the pyrethroid class of insecticides is readily degraded by environmental microorganisms(5,6) and based upon its structure, dimethrin is also expected to readily biodegrade(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 31,000(SRC), determined from a structure estimation method(2), indicates that dimethrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.6X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hours and 13 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 160 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 520(SRC), from an estimated log Kow of 6.57(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(9). Although biodegradation data for dimethrin are not available, the pyrethroid class of insecticides is readily degraded by environmental microorganisms(10,11) and based upon its structure, dimethrin is also expected to readily biodegrade(10,11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethrin, which has an estimated vapor pressure of 1.7X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase dimethrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase dimethrin may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Acute Toxicity LinkChemical: DIMETHRIN
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dimethrin can be estimated to be 31,000 (SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethrin is expected to be immobile in soil(SRC).

Human Toxicity Excerpts · 2 items

The clinical manifestations of inhalation exposure to pyrethrins can be local or systemic. Localized reactions confined to the upper respiratory tract include rhinitis, sneezing, scratchy throat, oral mucosal edema, and even laryngeal mucosal edema. Localized reaction of the lower respiratory tract include cough, shortness of breath, wheezing, and chest pain. An asthma like reaction occurs with acute exposures in sensitized patients. Hypersensitivity pneumonitis characterized by chest pain, cough, dyspnea, & bronchospasm may occur in an individual chronically exposed. /Pyrethrum and synthetic pyrethroids/

The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/

Artificial Pollution SourcesDimethrin's former(2) production and use as an insecticide(1) may have resulted in its direct release to the environment(SRC).
Environmental Biodegradation · 1 item

Although environmental biodegradation data specific to dimethrin are not available, the pyrethroid class of insecticides is readily degraded by environmental microorganisms(1,2); based upon its structure, dimethrin are also expected to readily biodegrade(1,2).

Environmental Bioconcentration · 1 item

An estimated BCF of 520 was calculated for dimethrin(SRC), using an estimated log Kow of 6.57(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(4).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for dimethrin is estimated as 7.6X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethrin is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 13 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 160 years if adsorption is considered(3). Dimethrin's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Dimethrin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 items

... Male and female albino rabbits (two/sex/dose) and male albino Wistar-CWL rats (five/dose) were given a single dose of 10 or 15 ml/kg (9.8 or 14.7 mg/kg) of technical grade dimethrin (98% pure) by gavage. Albino guinea pigs (four/sex) received a single dose of 10 ml/kg (9.8 mg/kg) by gavage. No effects were observed in rats or rabbits during a 2 wk observation period. ... In guinea pigs, the only effect ... was a refusal to eat or drink for 24 hr following dosing.

... 10 ml/kg (9.8 mg/kg) of technical grade dimethrin (98% pure) /was administered / to 15 male albino Wistar-CWL rats by gavage, 5 days/wk for 3 wk. This corresponds to an average daily dose of 7 mg/kg. No adverse effects, as judged by general appearance, behavior and growth, were observed. At necropsy, no gross abnormalities were observed.

... Single or multiple (3 consecutive days) instillations of 0.1 ml of undiluted dimethrin (98% pure) into the conjunctival sac of eight albino rabbits caused no visible irritation or chemosis and no injury of the cornea as detectable by means of fluorescein staining. When 0.2 ml of dimethrin was applied to the penile mucosa of five albino rabbits on two occasions 6 days apart, no irritation or sloughing of the mucosa was observed during a 1 week observation period.

... Dimethrin (98% pure) /was applied/ to the skin of albino rabbits (five/dose) 5 days/wk for 13 wk (65 applications). Doses admin were 0.5 ml/kg undiluted dimethrin or 0.5 ml/kg of a 50% soln of dimethrin in cottonseed oil (= to 0.25 ml/kg of dimethrin); controls received 0.5 ml/kg of cottonseed oil only. No evidence of any cutaneous reaction was observed. Occasionally, a slight, nonpersistent erythema was observed in all groups of rabbits. At necropsy, all organs from treated animals were indistinguishable from controls. No histopathological differences between control & treated animals were observed.

For more Non-Human Toxicity Excerpts (Complete) data for DIMETHRIN (6 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of dimethrin with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of dimethrin with photochemically- produced ozone has been estimated as 4.3X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 38 minutes at an atmospheric concentration of 7X10+11 hydroxyl radicals per cu cm(2). Reaction with nitrate radicals with vapor-phase dimethrin may also be an important degradation mechanism in air(SRC). A base-catalyzed second-order hydrolysis rate constant of 4.0X10-2 l/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 5.5 years and 200 days at pH values of 7 and 8, respectively(3).

Regulatory information

State Drinking Water Guidelines(ME) MAINE 2100 ug/l
Federal Drinking Water GuidelinesEPA 2000 ug/l

Safety data

ridadr
3082
hazard_class
9
packing_group
III
Hazardous Substances Data
70-38-2(Hazardous Substances Data)
Description

UsesDimethrin is a pesticide, a pyrethroid insecticide. An acaricide for agricultural purposes.

Suppliers6 total

上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
上海杰股生物科技有限公司021-51698675 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]