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Name:	Deltamethrin
CAS No:	52820-00-5
CAS No:	52918-63-5

PRODUCT DESCRIPTION

【Name】: Cyclopropanecarboxylicacid, 3-(2,2-dibromoethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester

【CAS Registry number】: 52820-00-5, 52918-63-5

【Synonyms】: NRDC 156
NRDC 158
RU 22950

【EINECS(EC#)】: 258-256-6

【Molecular Formula】: C22H19 Br2 N O3 (Products with the same molecular formula)

【Molecular Weight】: 505.20

【Inchi】: InChI=1/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3

【Canonical SMILES】: CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Br)Br)C

【MOL File】
52820-00-5.mol

Chemical and Physical Properties

【Density】: 1.595g/cm³

【Melting Point】: 101-102 deg C

【Boiling Point】: 535.8°Cat760mmHg

【Refractive Index】: 1.653

【Flash Point】: 277.8°C

【Solubilities】: Acetone: 500 g/l @ 20 deg C
Sol in ethanol, acetone, dioxane.
Water solubility=
Acetone (500 g/l), ethanol (15 g/l), cyclohexanone (750 g/l), dioxan (900 g/l), xylene (250 g/l), ethyl acetate.
Solubility; in cyclohexanone 750, dichloromethane 700, benzene 450, dimethyl sulphoxide 450, xylene 250, isopropanol 6 (all in g/l at 20 deg C)
In water, 0.002 mg/l @ 25 deg C

【Color/Form】: Crystals
Colorless crystals
White or slightly beige powder

【Spectral properties】: Specific rotation: +61 deg (40 g/l benzene)

【Computed Properties】: Molecular Weight:505.19916 [g/mol]
Molecular Formula:C₂₂H₁₉Br₂NO₃
XLogP3:6.2
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:7
Exact Mass:504.971122
MonoIsotopic Mass:502.973169
Topological Polar Surface Area:59.3
Heavy Atom Count:28
Formal Charge:0
Complexity:643
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:3
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Hydrophobe Count:4
Feature 3D Ring Count:2
Effective Rotor Count:7.6
Conformer Sampling RMSD:1.4
CID Conformer Count:240

Safety and Handling

【Skin, Eye, and Respiratory Irritations】: The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes.

【Cleanup Methods】: Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning, or by dissolving them in water, or other solvent in the factory environment. /Pesticides/

【Fire Fighting Procedures】: Use carbon dioxide, foam, or dry chemical /on fires involving pyrethroids/. /Pyrethrum/
Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode. /Pyrethrum/

【Formulations/Preparations】: USEPA/OPP Pesticide Code 097805; Trade Names: DECIS, FMC 45498, NRDC 161, Butoflin, Butox, Othrin, RU 22974, Othrine dust, striker IEC Insecticide (097805+121501).
Emulsifiable concentrate; wettable powder; ULV liquid; suspension concentrate; granules; dustable powder, fogging concentrate.
Mixed formulations: (deltamethrin +) heptenophos, sulphur
Domestic Bulgarian insecticide "Dekazol" /contains/ 0.02, 0.04, or 0.08% deltamethrin ... .

【Reactivities and Incompatibilities】: Incompatibility: Strong oxidizers. /Pyrethrins/
... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/

【Other Preventative Measures】: Skin that becomes contaminated with /pyrethrum/ should be promptly washed or showered with soap or mild detergent and water. /Pyrethrum/
Clothing contaminated with /pyrethrum/ should be placed in closed containers for storage until provision is made for the removal of /pyrethrum/ from the clothing. /Pyrethrum/
Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail or need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. /Pyrethrum/
Employees who handle /pyrethrum/ ... should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Pyrethrum/
Avoid contact with skin. Keep out of any body of water. Do not contaminate water by cleaning of equipment or disposal of waste. Do not reuse empty container. Destroy it by perforating or crushing. /Pyrethrum/
Workers should wash: Promptly when skin becomes contaminated. /Pyrethrins/
Work clothing should be changed daily: If it is reasonably probable that the clothing may be contaminated. /Pyrethrins/
Remove clothing: Promptly if it is non-impervious clothing that becomes contaminated. /Pyrethrins/
If /pyrethrins/ are not involved in a fire: keep /pyrethrins/ out of water sources and sewers. Build dikes to contain flow as necessary. /Pyrethrins/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

【Protective Equipment and Clothing】: Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/
Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/
Wear appropriate equipment to prevent: Repeated or prolonged skin contact. /Pyrethrum and pyrethrins/
Wear eye protection to prevent: Reasonable probability of eye contact. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 50 mg/cu m: Respirator Classes: Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. Any supplied-air respirator. May require eye protection. Any self-contained breathing apparatus. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 125 mg/cu m: Respirator Classes: Any supplied-air respirator operated in a continuous flow mode. May require eye protection. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 250 mg/cu m: Respirator Classes: Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece. Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 5,000 mg/cu m: Respirator Class: Any supplied-air respirator with a full facepiece and operated in a pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Classes: Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode. Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Classes: Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus. /Pyrethrins/

【Octanol/Water Partition Coefficient】: log Kow= 6.20

【Disposal Methods】: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incineration would be an effective disposal procedure where permitted. ... /Pyrethrin products/

Use and Manufacturing

【Use and Manufacturing】: Methods of Manufacturing

Deltamethrin is ... /a/ pyrethroid composed of a single isomer of 8 stereoisomers selectively prepared by the esterification of [1R, 3R or cis]-2,2-dimethyl-3-(2,2- dibromovinyl) cyclopropanecarboxylic acid with (alpha S)- or (+)-alpha-cyano-3- phenoxybenzyl alcohol or by selective recrystallization of the racemic esters obtained by esterification of the (1R, 3R or cis)-acid with the racemic or [alpha R, alpha S, or alpha RS or + or -]-alcohol.

Biomedical Effects and Toxicity

【Pharmacological Action】: - Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

【Therapeutic Uses】: Pyrethrins with piperonyl butoxide are used for topical treatment of pediculosis(lice infestations). Combinations of pyrethrins with piperonyl butoxide are not effective for treatment of scabies (mite infestations). Although there are no well-controlled comparative studies, many clinicians consider 1% lindane to be pediculicide of choice. However, some clinicians recommend use of pyrethrins with piperonyl butoxide, esp in infants, young children, & pregnant or lactating women ... . If used correctly, 1-3 treatments ... are usually 100% effective ... Oil based (eg, petroleum distillate) combinations ... produce the quickest results. ... For treatment of pediculosis, enough gel, shampoo, or solution ... should be applied to cover affected hair & adjacent areas ... After 10 min, hair is ... washed thoroughly ... treatment should be repeated after 7-10 days to kill any newly hatched lice. /Pyrethrins/

【Biomedical Effects and Toxicity】: In rats, following oral administration, elimination occurs within 2-4 days. The phenyl ring is hydroxylated, the ester bond hydrolyzed, and the acid moiety is eliminated as the glucuronide and glycine conjugated.
Three young male human volunteers underwent a complete medical check-up one week prior to the morning of the study. Each of them received a single dose of 3 mg of (14)C deltamethrin mixed in 1 g glucose and diluted first in 10 ml polyethylene glycol300 and again in 150 ml water. Total radioactivity was 1.8 + or - 0.9 mBq. Samples of blood, urine, saliva, and feces were taken at intervals over 5 days. Clinical and biological examinations were performed every 12 hr during the trial and one week after its termination. Radioactivity in the biological samples was measured with a liquid scintillation spectrometer. The clinical and biological checks did not detect any abnormal findings. There were no signs of side effects ... either during or after the trial period. The maximum plasma radioactivity appeared between 1 and 2 hr after administration of the product, and remained over the detection limit (0.2 KBq/l) during the 48 hr. The apparent elimination half-life was between 10.0 and 11.5 hr. The radioactivity of blood cells, as well as the saliva, was extremely low. Urinary excretion was 51-50% of the initial radioactivity; 90% of this radioactivity was excreted during the 24 hr following absorption. The apparent half-life of urinary excretion was 10.0-13.5 hr, which is consistent with the plasma data. Fecal elimination at the end of the observation period represented 10-26% of the dose. The total fecal plus urine elimination was around 64-77% of the initial dose after 96 hr.
In a feeding study, deltamethrin was administered twice daily to lactating dairy cows in portions of their daily feed at the rate of 2 or 10 mg/kg diet for 28 consecutive days. The level of 2 mg/kg diet was the residue level found in a recently treated pasture, whereas 10 mg/kg diet was five times this level. Deltamethrin residues in the milk were dose-dependent and appeared to reach a plateau between 7 and 9 days after the start of treatment. At the high deltamethrin intake of 10 mg/kg diet, the deltamethrin residue in milk was about 0.025 mg/l. Deltamethrin residues in tissues were measured 1, 4, and 9 days after the last dose. At the 10 mg/kg diet intake, very small amounts of deltamethrin residues were found in the liver (
In a metabolic study, (14)C-deltamethrin was administered orally to lactating dairy cows at the rate of 10 mg/kg body weight per day for 3 consecutive days. It was poorly absorbed and mainly eliminated in the feces as unchanged deltamethrin. Only 4-6% of the administered (14)C was eliminated in the urine, and 0.42-1.62% was secreted in the milk. The radiocarbon contents of various tissues were generally very low with the exception of those of the liver, kidney, and fat, which were higher. Deltamethrin degradation occurred by cleavage of the ester bond, as already reported in rats and mice. The enzymes responsible for the ester bond cleavage were located in cow liver homogenate, mainly in the microsomal fraction, as seen in an in vitro study. Metabolites resulting from ester bond cleavage further metabolized and/or conjugated, resulting in a large number of compounds excreted in the urine. In the milk, the major identifiable radiolabelled compound was deltamethrin.
The fate of (14)C-deltamethrin was examined in Leghorn hens. When laying hens were administered 7.5 mg of (14)C-labelled deltamethrin/hen per day orally for 3 consecutive days, about 83% and 90% of the administered (14)C was eliminated during the first 24 hr and 48 hr after dosing, respectively. Tissue residues were generally very low with the exception of those in the liver and kidney. Very low levels of residues were found in eggs obtained within the first 24 h after dosing, but levels increased reaching a peak within 48 hr of the last dose. Residue levels were higher in the yolk (up to 0.6 mg/kg) than the albumen (up to 0.2 mg/kg), which is probably related to the lipid content of yolks. Metabolites were the same as those found in rats and mice.
The comparison between the excreted radioactivity of (14)C- deltamethrin in rats treated by the percutaneous route and iv (controls) showed the only 3.6% of the dosage applied on the skin was absorbed and excreted in 24 hr with 1.1% excreted during the first 6 hr. Since rat skin is more permeable than human skin, the uptake of deltamethrin through the human skin should be relatively weak.
After oral administration to male rats at 0.64-1.60 mg/kg, the acid and alcohol moieties of deltamethrin were almost completely eliminated from the body within 2-4 days. On the other hand, the cyano group was eliminated more slowly, the total recovery during 8 days being 79% of the radiocarbon dose (43% and 36% in the urine and feces, respectively). Tissue residues of deltamethrin labelled with (14)C at the dibromovinyl carbon in the acid moiety and the benzylic carbon in the alcohol moiety were generally very low, whereas residue levels in the fat were somewhat higher (0.1-0.2 mg/kg). Residue levels of the radiocarbon derived from the cyano group were relatively high, especially in the skin and stomach. Essentially, all the radiocarbon in the stomach was thiocyanate. No noticable (14)CO2 was evolved from any of the radioactive preparations, including the CN-labelled group, in contrast to the CN group from fenvalerate, which yielded (14)CO2 in considerable amounts.
Lactating dairy cows were fed deltamethrin (2 or 10 mg/kg feed) for 28 consecutive days and deltamethrin residues were then measured in milk and tissues. Deltamethrin residues were higher relative to dose administered. The order of relative concentrations of deltamethrin in tissues, measured 1, 4, and 9 days after the last dose was: renal fat > subcutaneous fat > forequarter muscle > hindquarter muscle > liver > kidney. Depletion of deltamethrin residues in milk was very rapid indicating that half-life of the insecticide of about 1 day. Trace amounts of deltamethrin metabolites 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylic acid (
/PYRETHROIDS/ READILY PENETRATE INSECT CUTICLE AS SHOWN BY TOPICAL LD50 TO PERIPLANETA (COCKROACH) ... /PYRETHROIDS/
WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/ [MIYAMOTO J; ENVIRON HEALTH PERSPECT 14: 15-28 (1976)] PubMed Abstract
Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/
The distribution of (14)C-acid-, (14)C-alcohol-, and (14)C-cyano-labelled deltamethrin and selected metabolites in the liver, blood, cerebrum, cerebellum, and spinal cord /was studied/ after iv administration of a toxic, but non-lethal, dose (1.75 mg/kg) to rats. Approximately 50% of the dose was cleared from the blood within 0.7-0.8 min, after which the rate of clearance decreased. 3-Phenoxybenzoic acid (PBacid) was isolated from the blood in vivo, and was also the major metabolite when (14)C-alcohol-labelled deltamethrin was incubated with blood in vitro. Deltamethrin levels in the liver peaked at 7-10 nmol/g at 5 min and then decreased to 1 nmol/g by 30 min. In contrast, peak central nervous system levels of deltamethrin were achieved within 1 min (0.5 nmol/g), decreasing to 0.2 nmol/g at 15 min and remaining stable until 60 min. Peak levels of deltamethrin were not related to the severity of toxicity, though the levels of unextractable pentane radiolabel did appear to be correlated with signs of motor toxicity.
Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/
The cutaneous and gastrointestinal absorption of deltamethrin in humans has been demonstrated after acute poisonings due to occupational overexposure or ingestion of deltamethrin products. The presence of a deltamethrin metabolite (3-2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylic acid) has been reported in the urine of people with acute deltamethrin intoxication, confirming the absorption and metabolic degradation of this insecticide in the human body.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: A base-catalyzed second-order hydrolysis rate constant of 6.1X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(1). This corresponds to half-lives of 36 and 3.6 years at pH values of 7 and 8, respectively(1). Deltamethrin was observed to undergo direct photolysis when hexane, acetonitrile-water, or water solutions were exposed to UV radiation >295 nm(2). In aqueous solution, the photolysis rate increased rapidly when a 2% acetone photosensitizer was added(2). Photolysis rates were slower in water than in hexane or acetonitrile-water(2). The photodegradation reaction went through racemization at the alpha position in the alcohol moiety, ester cleavage and reductive bromination(2). When cotton strips impregnated with deltamethrin were exposed to a UV lamp (simulating midday natural sunlight) for a 24-hr period, 31-99% of the initial deltamethrin degraded(3). The fastest degradation rates occurred on white fabric while the slowest rates occurred on black fabric(3); addition of 2,4-dihydroxybenzophenone (a UV absorber) reduced photodegradation rates(3). Deltamethrin, impregnated on cloth, has been observed to degrade rapidly when exposed to sunlight(4). The photodegradation half-life of deltamethrin in distilled and natural water solutions exposed to sunlight was found to range from 1 to less than 5 days(5). Deltamethrin also photodegraded as thin-films or when sprayed on potato leaves exposed to sunlight(5). Deltamethrin disappears much more rapidly from soil environments from surface application routes as compared to application routes that wash it into or incorporate it into the soil(6) which indicates the importance of photodegradation and volatilization(SRC). A field study involving 4 prairie ponds in Saskatchewan, Canada and aerial spraying found deltamethrin half-lives of 0.6-5 hr in the surface-film formed by the spraying and an avg half-life of 14-hr in the subsurface water(7); degradation products included a cyclopropyl acid derivative and phenoxybenzoic acid(7). In a field study using two small ponds and subsurface injections of deltamethrin, a water column disappearance half-life of 2-4 hr was observed with rapid partitioning to sediment and suspended solids (disappearance included transport, degradation and partitioning)(8); the disappearance half-life in the sediment was 5-14 days(8); major degradation products were cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-carboxylic acid and 3-phenoxybenzoic acid(8).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Use and Manufacturing

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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