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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)
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
45681
Product name
Tetramethrin
Purity
PESTANAL?, analytical standard
Packaging
250mg
Price
$104
Updated
2024/03/01
Sigma-Aldrich
Product number
CRM03054
Product name
Tetramethrin
Purity
mixture of isomers, certified reference material, TraceCERT?
Packaging
100MG
Price
$100
Updated
2022/05/15
TRC
Product number
T298690
Product name
Tetramethrin
Packaging
1g
Price
$135
Updated
2021/12/16
AK Scientific
Product number
M948
Product name
Tetramethrin
Packaging
1g
Price
$268
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

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View Lastest Price from Tetramethrin manufacturers

Hebei Duling International Trade Co. LTD
Product
Tetramethrin 7696-12-0
Price
US $9.90/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2022-10-17
Hubei Langyou International Trading Co., Ltd
Product
Tetramethrin 7696-12-0
Price
US $100.00/KG
Min. Order
1KG
Purity
95%
Supply Ability
10000 tons
Release date
2021-08-19
Hebei Yanxi Chemical Co., Ltd.
Product
Tetramethrin 7696-12-0
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-09-19

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