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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
Molecular Weight:
331.41
MDL Number:
MFCD00084635
MOL File:
7696-12-0.mol
MSDS File:
SDS
Last updated:2024-10-28 23:16:16

Tetramethrin 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. Sealed in dry,2-8°C
solubility Soluble in DMSO
form Solid
Water Solubility 1.83 mg l-1 (25 °C)
pka -2.55±0.20(Predicted)
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)
EWG's Food Scores 1-3
FDA UNII Z72930Q46K
ATC code P03BA04
NIST Chemistry Reference Tetramethrin(7696-12-0)
Pesticides Freedom of Information Act (FOIA) Tetramethrin
EPA Substance Registry System Tetramethrin (7696-12-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H302-H331-H351-H371-H410
Precautionary statements  P201-P202-P273-P301+P312-P304+P340+P311-P308+P311
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
Toxicity LD50 orally in mice: 1000 mg/kg (Kato)

Tetramethrin price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45681 Tetramethrin PESTANAL?, analytical standard 7696-12-0 250mg $104 2024-03-01 Buy
Sigma-Aldrich CRM03054 Tetramethrin mixture of isomers, certified reference material, TraceCERT? 7696-12-0 100MG $100 2022-05-15 Buy
TRC T298690 Tetramethrin 7696-12-0 1g $135 2021-12-16 Buy
AK Scientific M948 Tetramethrin 7696-12-0 1g $268 2021-12-16 Buy
AK Scientific M948 Tetramethrin 7696-12-0 100mg $95 2021-12-16 Buy
Product number Packaging Price Buy
45681 250mg $104 Buy
CRM03054 100MG $100 Buy
T298690 1g $135 Buy
M948 1g $268 Buy
M948 100mg $95 Buy

Tetramethrin Chemical Properties,Uses,Production

Description

Form: Colorless crystals with slight pyrethrum-like odor

Chemical Properties

white crystals or powder

Uses

Insecticide.

Uses

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

Uses

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

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.

Toxicity evaluation

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

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.

Global( 260)Suppliers
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Shaanxi Dideu Medichem Co. Ltd
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View Lastest Price from Tetramethrin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tetramethrin pictures 2024-11-22 Tetramethrin
7696-12-0
US $65.00-20.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
Tetramethrin pictures 2024-10-28 Tetramethrin
7696-12-0
US $0.00-0.00 / KG 1KG 99% 500000kg Hebei Weibang Biotechnology Co., Ltd
Tetramethrin pictures 2024-10-25 Tetramethrin
7696-12-0
US $0.00 / kg 1kg 0.99 20tons Hebei Yanxi Chemical Co., Ltd.
  • Tetramethrin pictures
  • Tetramethrin
    7696-12-0
  • US $65.00-20.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
  • Tetramethrin pictures
  • Tetramethrin
    7696-12-0
  • US $0.00-0.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd
  • Tetramethrin pictures
  • Tetramethrin
    7696-12-0
  • US $0.00 / kg
  • 0.99
  • Hebei Yanxi Chemical Co., Ltd.
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 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 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 sumitomosp-1103 tetralate thyl-1-propenyl)cyclopropanecarboxylate. weo-pynamin 3,4,5,6-TETRAHYDROPHTHALIMIDOMETHYL (1RS)-CIS-TRANS-CHRYSANTHEMATE