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| | Deltamethrin Basic information |
| | Deltamethrin Chemical Properties |
| Melting point | 98°C | | Boiling point | 300°C | | alpha | +56～+64°(20℃/D)(c=4,C6H6) | | density | 1.5214 (rough estimate) | | vapor pressure | 1.24×10-2Pa (25 °C) | | refractive index | 1.6220 (estimate) | | Fp | -18 °C | | storage temp. | −20°C | | solubility | Soluble in DMSO (up to 50 mg/ml) | | Water Solubility | <0.0002 mg l-1 (25 °C) | | form | Crystalline | | color | Colorless | | λmax | 278nm(Hexane)(lit.) | | Merck | 14,2883 | | BRN | 6746312 | | Stability: | Stable. Incompatible with acids, alkalies, strong oxidizing agents. | | LogP | 6.200 | | IARC | 3 (Vol. 53) 1991 | | NIST Chemistry Reference | Deltamethrin(52918-63-5) | | EPA Substance Registry System | Deltamethrin (52918-63-5) |
| | Deltamethrin Usage And Synthesis |
| Description | Deltamethrin is a type II pyrethroid insecticide and a modulator of voltage-gated sodium channels (Nav). It binds to Drosophila para Nav channels in a use-dependent manner following brief depolarizing prepulses and with increasing concentrations of 1 to 5 nM, indicating that it preferentially binds to the channel in the open state. It slowly activates Nav1.8 channels, delays inactivation by longer than 40 ms, and induces persistent tail currents for channels expressed in X. laevis oocytes. Deltamethrin decreases proliferation of MCF-7 cells and inhibits androgen receptor transactivation when used at concentrations of 10 and 20 μM or greater, respectively. However, it is not cytotoxic to MCF-7 and CHO cells at concentrations of 25 and 100 μM, respectively, and does not induce transactivation of the estrogen receptor. Deltamethrin is lethal to mice with an LD50 value of 50 mg/kg and at low sublethal doses of 0.05 and 0.1 mg/kg it induces histopathological changes in the liver, kidney, spleen, and testes, including a loss of spermatozoa and Sertoli cells. | | Description | Deltamethrin is a kind of synthetic pyrethroids insecticide used worldwide in agriculture for home pest control and protection of foodstuff and disease vector control. Deltamethrin belongs to the type II pyrethroids, which is hydrophobic in nature. It kills the insects through producing severe delay in sodium channel inactivation, leading to a persistent depolarization of the nerve membrane without repetitive discharge. However, this pesticide can be contained in contaminated food and water, and is readily absorbed by the oral route. Recent studies have shown that it can have certain toxicity through inducing oxidative stress. Vitamin can be used to alleviate its toxicity.
| | Chemical Properties | Colorless, white, or off-white crystalline solid
or powder. Odorless. Combustible. | | Chemical Properties | White Powder | | Uses | A Type II pyrethroid insecticide that potently inhibits calcineurin | | Uses | Synthetic pyrethroid insecticide, which acts as a potent inhibitor of calcineurin (protein phosphatase 2B) and has an IC50 of about 100pM. This inhibition action results in cellular hyperexcitability by causing non-mutated calcium channels to remain open for an extended period of time allowing an abundance of Ca2+ to enter the cell. | | Uses | Insecticide. | | Uses | Deltamethrin is effective against a wide range of insects in fruit,
cereals, vegetables, cotton, soyabeans and oilseed rape. It is also used for
the control of crawling and flying insects indoors, in stored grain and
timber and for ectoparasite control on animals. | | Definition | ChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. | | Contact allergens | Pyrethroids, also called pyrethrinoids, are neurotoxic
synthetic compounds used as insecticides, with irritant
properties. Cypermethrin and fenvalerate have been
reported as causing positive allergic patch tests, but
only fenvalerate was relevant in an agricultural worker. | | Potential Exposure | Deltamethrin is a synthetic pyrethroid
insecticide that kills insects on contact and through diges-
tion. It is used to control a variety of chewing and sucking
insects that infest fruit, vegetables and field crops, includ-
ing apples, pears and plums; peas, glasshouse cucumbers,
tomatoes, peppers, potted plants, and ornamentals; hops,
oats, cotton and other field crops. Deltamethrin is also used
to control residential and commercial insect pests. Some
formulations are RUPs) | | Environmental Fate | Deltamethrin is a type II pyrethroid, a functional neurotoxin
slowing the inactivation of voltage-gated sodium channels
leading to a state of hyperexcitability which in turn causes fine
tremor, salivation, and choreoathetosis. Other proposed
contributory actions include antagonism of gammaaminobutyric
acid A receptor inhibition and voltage-gated
chloride and calcium channels. | | Metabolic pathway | After oral administration of 14C-deltamethrin to
lactating dairy cows, deltamethrin is metabolized and
excreted in the bile and urine with very little
accumulation in major edible tissues. The major
portion (78-82%) of the radioactivity in feces is
deltamethrin. Only 4-6% is eliminated in the urine and
0.42 ? 1.62% is secreted in the milk. The primary
biotransformation is via the hydrolysis of the ester
linkage followed by oxidation of the geminal methyl
groups of cyclopropane carboxylic acids and phenoxy
benzaldehyde, resulting in dicarboxylic acid,
lactonecarboxylic acid, or phenoxybenzoic acid derivatives. Deltamethrin is not metabolized within
algae cells and mouse fibroblasts, but is partially
transformed into less or not active isomers. In algae
and fibroblast culture media, many metabolites of
deltamethrin resulting mostly from hydrolysis of the
molecule are found. This metabolism seems to be
linked with the release of enzymes by cells into the
culture medium. | | Shipping | UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.UN3349 Pyrethroid pesticide, solid toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | | Degradation | Deltamethrin is very stable as a solid but it is readily hydrolysed in solution
under alkaline conditions with a DT50 of 2.5 days at pH 9 (25 °C). By
analogy with cypermethrin, the rate-determining step in dilute solution is
nucleophilic attack by OH-.
Isomerisation has been shown to occur in natural waters under dark
conditions, yielding the inactive 1 ScisaS isomer (Maguire, 1992). Aqueous
photolysis (sunlight) causes slow degradation but also isomerism to the
insecticidally active 1RtransaS form. These isomerisation reactions, which
are more rapid than those of cypermethrin, were reported much earlier by
Ruzo et al. (1977). This is due to the heavy atom effect (bromine).
Similarly, the decreased bond strength of C-Br (ct C-Cl) leads to photocatalysed
reductive debromination, with tans- favoured over cisdebromination
by a factor of 4. The DT50 on soil photolysis is 9 days (PM).
Photolysis of the ester bond is the main reaction of deltamethrin.
Solvent effects are important. cis-3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropanecarboxylic
acid (2) and 3PBA (4) are the major products in
water (Scheme 1). A minor product (5) was formed by decarboxylation.
Deltamethrin is resistant to photo-oxidation. The mechanisms of photodegradation of the pyrethroids have been reviewed by Ruzo (1982). | | Toxicity evaluation | Deltamethrin is twofold more persistent in aquatic environments
than in soil. Depending on conditions the environmental
half-life ranges from 2 days (for hydrolysis at pH 9) to 80 days
(for degradation in an aquatic environment). | | Incompatibilities | May react violently with strong oxidi-
zers, bromine, 90% hydrogen peroxide, phosphorus
trichloride, silver powders or dust. Incompatible with silver
compounds. Mixture with some silver compounds forms
explosive salts of silver oxalate. | | Waste Disposal | ncineration would be an
effective disposal procedure where permitted. If an efficient
incinerator is not available, the product should be mixed
with large amounts of combustible material and contact
with the smoke should be avoided. In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. | | References | Adams, A. J. "A review of the efficacy and uses of deltamethrin for wood preservation." Document - the International Research Group on Wood Preservation (Sweden) (1996).
Sayeed, I, et al. "Oxidative stress biomarkers of exposure to deltamethrin in freshwater fish, Channapunctatus Bloch." Ecotoxicology & Environmental Safety 56.2(2003):295-301.
Yousef, Mokhtar I., T. I. Awad, and E. H. Mohamed. "Deltamethrin-induced oxidative damage and biochemical alterations in rat and its attenuation by Vitamin E." Toxicology 227.3(2006):240-247.
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| | Deltamethrin Preparation Products And Raw materials |
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