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Tetramethrin

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Tetramethrin Basic information

Product Name:
Tetramethrin
CAS:
7696-12-0
MF:
C19H25NO4
MW:
331.41
EINECS:
231-711-6
Mol File:
7696-12-0.mol
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Tetramethrin Chemical Properties

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. 
0-6°C
Water Solubility 
1.83 mg l-1 (25 °C)
form 
neat
pka
-2.55±0.20(Predicted)
Merck 
13,9296
BRN 
8807938
Stability:
Stable. Incompatible with strong oxidizing agents.
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 Information

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)

MSDS

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Tetramethrin Usage And Synthesis

Description

Form: Colorless crystals with slight pyrethrum-like odor

Chemical Properties

white crystals or powder

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.

Uses

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

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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TetramethrinSupplierMore

Hubei Jianwen Biomedical Co., Ltd. Gold
Tel:
18971192297 027-87883343-
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2644074018@qq.com
J & K SCIENTIFIC LTD.
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400-666-7788 010-82848833-
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jkinfo@jkchemical.com;market6@jkchemical.com
BEST-REAGENT
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18981987031 400-1166-196
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cdhxsj@163.com;1955352637@qq.com;cdhxsj@163.com
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel:
0571-82693216
Email:
info@yuhaochemical.com
Chengdu Ai Keda Chemical Technology Co., Ltd.
Tel:
4008-755-333 028-85911938-
Email:
800078821@qq.com
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