ChemicalBook > CAS DataBase List > Tetramethrin

Tetramethrin

Product Name: Tetramethrin
CAS No.: 7696-12-0
Chemical Name: Tetramethrin
Synonyms: TTM;biwenan;PHTHALTHRIN;etramethrin;TetraMethirn;d-phthalthrin;tetramethrine;1-cyclohexene-1,2-dicarboximidomethyl-2,2-dimethyl-3-(2-dimethyl-1-propenyl)cy;Doom;sp1103
CBNumber: CB9420520
Molecular Formula: C19H25NO4
Formula Weight: 331.41
MOL File: 7696-12-0.mol

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Tetramethrin Property

Melting point:: 60-80°C
Boiling point:: 468.68°C (rough estimate)
Density: d2020 1.108
vapor pressure: 0.94×10^-3 Pa (30 °C)
refractive index: nD21.5 1.5175
storage temp.: Sealed in dry,2-8°C
solubility: Soluble in DMSO
Water Solubility: 1.83 mg l^-1 (25 °C)
pka: -2.55±0.20(Predicted)
form: Solid
color: Off-white to light yellow
Merck: 13,9296
BRN: 8807938
Stability:: Stable. Incompatible with strong oxidizing agents.
LogP: 4.730
CAS DataBase Reference: 7696-12-0(CAS DataBase Reference)
NIST Chemistry Reference: Tetramethrin(7696-12-0)
EPA Substance Registry System: Tetramethrin (7696-12-0)

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Safety

Hazard Codes: Xn,N
Risk Statements: 20-50/53
Safety Statements: 24/25-61-60
RIDADR: UN 2588
WGK Germany: 2
RTECS: GZ1730000
HazardClass: 9
PackingGroup: III
HS Code: 29251900
Hazardous Substances Data: 7696-12-0(Hazardous Substances Data)
Toxicity: LD50 orally in mice: 1000 mg/kg (Kato)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H331Toxic if inhaled

H351Suspected of causing cancer

H371May cause damage to organs

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: CRM03054
Product name: Tetramethrin
Purity: mixture of isomers, certified reference material, TraceCERT?
Packaging: 100MG
Price: $112
Updated: 2025/07/31

Sigma-Aldrich

Product number: 45681
Product name: Tetramethrin
Purity: PESTANAL?, analytical standard
Packaging: 250mg
Price: $106
Updated: 2025/07/31

TCI Chemical

Product number: T4038
Product name: Tetramethrin (mixture of isomers)
Packaging: 5G
Price: $65
Updated: 2025/07/31

TRC

Product number: T298690
Product name: Tetramethrin
Packaging: 1g
Price: $135
Updated: 2021/12/16

AK Scientific

Product number: M948
Product name: Tetramethrin
Packaging: 100mg
Price: $95
Updated: 2021/12/16

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Tetramethrin Chemical Properties,Usage,Production

Description

Form: Colorless crystals with slight pyrethrum-like odor

Chemical Properties

white crystals or powder

Uses

Tetramethrin is used to control flies, wasps, cockroaches and other insects in public health, home and garden situations.

Uses

Tetramethrin is a synthetic pyrethroid pesticide used in large-scale commercial agricultural applications as well as in consumer products for domestic purposes.

Uses

Insecticide.

Definition

ChEBI: Tetramethrin is a phthalimide insecticide, a member of maleimides and a cyclopropanecarboxylate ester. It has a role as a pyrethroid ester insecticide. It is functionally related to a chrysanthemic acid.

General Description

Colorless crystals with slight odor. Non corrosive. Used as an insecticide.

Air & Water Reactions

Hydrolysis occurs with strong acid or base.

Reactivity Profile

A pyrethroid. Tetramethrin is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Agricultural Uses

Insecticide: Tetramethrin is often formulated as an aerosol and used primarily for indoor pest control or in mosquito coils. It is also used in shampoos to control fleas and ticks on pets. It is often formulated with other insecticides and synergists. Not approved for use in EU countries. Registered for use in the U.S.

Trade name

FMC 9260®; ENT-27339; EVERCIDE INTERMEDIATE® 2265 (tetramethrin + fenvalerate); MULTICIDE®; NEO-PYNAMIN®; NEOPYNAMINE®; NEOPYNAMIN FORTE®; NIAGARA®-9260; NIA®- 9260; PHTHALTHRIN®; SP-1103; SUMITOMO® SP-1103

Metabolic pathway

Tetramethrin was the second synthetic pyrethroid to be produced commercially (1964). The compound has a rapid knock-down action and a reasonable killing activity which is enhanced by use with synergists. It is usually used with piperonyl butoxide and in the presence of other insecticides. It has two chiral centres, both in the acid group, and therefore is a 1 RS-cis-trans mixture. A(1R)-rich product containing cis- and trans-isomers in the ratio 20:80 is also used in public health; this is named dtetramethrin. The two products will not be distinguished here because metabolic studies have been performed with various combinations of isomers. Most published information relates to its mode of action in insects and its metabolism in rodents. This is a reflection of its limited outdoor and field use.

Degradation

Tetramethrin is a stable chemical but it is base labile and it is also sensitive to strong acids. It is hydrolysed to (1RS)-cis-trans-2,2-dimethyl-3-(2- methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid, 2) and tetrahydrophthalimide (4). It is oxidised by m-chloroperbenzoic acid to form epoxy-tetramethrin (5) which is ring-opened to the diol (6) in dilute aqueous acid (Smith and Casida, 1981). This reaction has been postulated as initiating the opening of the cyclopropane ring with the ultimate formation of CO ₂ in biological systems (see below). Another biomimetic reaction of tetramethrin and its ester cleavage product 4 is Michael addition of thiols to the double bond. Glutathionyl-tetramethrin (7) is formed by incubation of the constituents in buffered aqueous methanol (Smith et al., 1982). Its formation on incubation with mouse liver microsomes is probably non-enzymatic. At the time of this discovery there appeared to be no equivalent reaction in vivo but the more recent discovery of sulfonate metabolites (see below) demonstrates its role.
The chrysanthemic acid esters are very sensitive to photodegradation, being subject to ring-opening initiated by the formation of epoxides such as 5 (Ruzo et al., 1982) as described under bioallethrin and phenothrin. Isomerisation was observed only in de-oxygenated benzene solution because photo-oxidative degradation predominated under most conditions. Many products were seen in oxygenated benzene solution and in a thin film in sunlight.
These chemical and photochemical reactions are summarised in Scheme 1.

Toxicity evaluation

Acute oral LD₅₀ for rats: >5,000 mg/kg

Tetramethrin Preparation Products And Raw materials

Raw materials

1,2,3,6-Tetrahydrophthalic anhydride 1,6-Hexanediol Formaldehyde CHLOROETHANE Glycine ethyl ester hydrochloride Urea Tetrahydrophthalimide Phthalic acid Phosphorus trichloride Permethric acid 3,4,5,6-Tetrahydrophthalic anhydride Ethyl chrysanthemumate Chrysanthemoyl chloride

Preparation Products

Sanitary pesticide

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View Lastest Price from Tetramethrin manufacturers

Qingdao Trust Agri Chemical Co.,Ltd

Product: Tetramethrin 7696-12-0
Price: US $0.00/kg
Min. Order: 1kg
Purity: 95
Supply Ability: 20tons
Release date: 2025-09-28

RongNa Biotechnology Co.,Ltd

Product: Tetramethrin 7696-12-0
Price: US $10.00/ASSAYS
Min. Order: 1ASSAYS
Purity: 99%
Supply Ability: 1 ton
Release date: 2025-08-21

Shaanxi Dideu Medichem Co. Ltd

Product: Tetramethrin 7696-12-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 1T
Release date: 2025-04-29

7696-12-0, TetramethrinRelated Search:

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1-cyclohexene-1,2-dicarboximidomethyl-2,2-dimethyl-3-(2-dimethyl-1-propenyl)cy

1-cyclohexene-1,2-dicarboximidomethyl-2,2-dimethyl-3-(2-methylpropenyl)cyclopr

2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylicacidesterwithn-(hydr

2,3,4,5-tetrahydrophthalimidomethylchrysanthemate

3,4,5,6,7-2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylicacid(1

3,4,5,6-tetrahydrophthalimidomethyl(+-)-cis,trans-chrysanthemate

3,4,5,6-Tetrahydrophthalimido-methyl(±)cis,trans-chrysanthemate

3,4,5,6-tetrahydrophthalimidomethylcisandtransdlchrysanthemummonocarboxy

3,4,5,6-tetrahydro-phthalimidomethylesterderdl-cis-trans-chrysanthemumsaeur

(1-cyclohexane-1,2-dicarboximido)methylchrysanthemumate

(1-cyclohexene-1,2-dicarboximido)methylchrysanthemumate

(1,3,4,5,6,7-hexahydro-1,3-dioxo-2h-isoindol-2-yl)methyl2,2-dimethyl-3-(2-me

TETRAMETHRIN 90

TETRAMETHRI

TETRAMETHRIN 97

Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl ester

phthalthrin (jmaf)

tetramethrin (bsi,iso,ansi)

tetramethrin [(1r)-isomers]

3,4,5,6-TETRAHYDROPHTHALIMIDOMETHYLCIS-CHRYSANTHEMATE

3,4,5,6-TETRAHYDROPHTHALIMIDOMETHYLTRANS-CHRYSANTHEMATE

(1-CYCLOHEXENE-1,2-DICARBOXIMIDO)METHYL2,2-DIMETHYL-3-(2-.

Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-propenyl)-,(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-methyl ester

(1,3,4,5,6,7-Hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

(1-Cyclohexene-1,2-dicarboximido)methyl 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylate

2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl ester

2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid 1,3,4,5,6,7-hexahydro-1,3-dioxy-2H-isoindol-2-yl)methyl ester

3，4，5，6-trtrahydrophthalimidomethyl-(±)cis,trans-chrysanthemate

TETRAMETHRIN, 100MG, NEAT

TETRAMETHRIN PESTANAL, 250 MG

Tetramethrin（mixture of isomers）

2,2-dimethyl-3-(2-methylprop-1-enyl)-1-cyclopropanecarboxylic acid (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl ester

biwenan

7-hexahydro-1,3-dioxo-2h-isoindol-2-yl)methylester

bioneopynamin

cyclohex-1-ene-1,2-dicarboximidomethyl(1rs)-cis,trans-2,2-dimethyl-3-(2-methy

cyclohex-1-ene-1,2-dicarboximidomethyl(1rs)-cis,trans-chrysanthemate

Cyclopropanecarboxylicacid,2,2-dimethyl-3-(2-methyl-propenyl)-,(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-methylester

d-phthalthrin

ent27339

fmc-9260

hexahydro-1,3-dioxo-2h-isoindol-2-yl)methylester

insectol

l-prop-1-enyl)cyclopropanecarboxylate

multicide

n-(3,4,5,6-tetrahydrophthalimide)methyl-cis,trans-chrysanthemate

n-(3,4,5,6-tetrahydrophthalimido)-methyldl-cis-trans-chrysanthemate

n-(chrysanthemoxymethyl)-1-cyclohexene-1,2-dicarboximide

neopinamin

neopynaminforte

nia-9260

niagarania-9260

nsc190939

oxymethyl)-1-cyclohexene-1,2-dicarboximide

py-kill

sp1103

sp-1103

sp1103forte