52315-07-8 Usage
Uses
Used in Agricultural Industry:
Cypermethrin is used as an insecticide for controlling a variety of insects on cotton, fruit, and vegetable crops. It is a U.S. EPA restricted Use Pesticide (RUP) and is also utilized in soybean, leeks, onions, carrots, turnips, swedes, parsnips, viola spp., spinach, black currant, gooseberries, sunflowers, linseeds, groundnuts, barley, and mushrooms.
Used in Household and Animal Husbandry:
Cypermethrin is used as a pesticide in household settings, as well as in animal husbandry, for the control of insects. It is commonly used to kill household insect pests and is the fourth most commonly-used insecticide in California.
Used in Public Health:
Cypermethrin is employed in public health for the control of Lepidoptera, beetles, and aphids. It is used in various applications, such as crack, crevice, and spot treatments.
Used as a Potent Inhibitor of Calcineurin:
Cypermethrin serves as a potent inhibitor of calcineurin, a phosphatase involved in various cellular processes.
Used as an Ectoparasiticide:
Cypermethrin is used as an ectoparasiticide, effectively reducing the survival of ticks, lice, and other external parasites. It has been shown to decrease the number of ticks on infested cattle and prevent re-infestation in contact-challenged sheep.
Toxicology
Cypermethrin is a moderately toxic material by dermal absorption or ingestion. Symptoms of high dermal exposure include numbness, tingling, itching, burning sensation, loss of bladder control, incoordination, seizures, and possible death. Pyrethroids like cypermethrin may adversely affect the central nervous system. Symptoms of high-dose ingestion include nausea, prolonged vomiting, stomach pains, and diarrhea which progresses to convulsions, unconsciousness, and coma. Cypermethrin is a slight skin or eye irritant, and may cause allergic skin reactions. The oral LD50 for cypermethrin in rats is 250 mg/kg (in corn oil) or 4123 mg/kg (in water). EPA reports an oral LD50 of 187 to 326 mg/kg in male rats and 150 to 500 mg/kg in female rats. The oral LD50 varies from 367 to 2000 mg/kg in female rats, and from 82 to 779 mg/kg in mice, depending on the ratio of cis/trans- isomers present. This wide variation in toxicity may reflect different mixtures of isomers in the materials tested. The dermal LD50 in rats is 1600 mg/kg and in rabbits is greater than 2000 mg/kg.
References
[1] DeeAn Jones, Environmental Fate of Cypermethrin
[2] http://www.inchem.org
[3] http://npic.orst.edu
Trade name
AMMO?; AGROTHRIN?; ARDAP?; ARRIVO?; AVICADE?; BARRICADE?; CCN52?; CNN 52?; CYMBUSH? 2E; CYMBUSH? 3E; CYMPERATOR?; CYNOFF?; CYPERCARE?; CYPERSECT?; CYPERKILL?; CYRUX?; DEMON?; DORSAN-C? (+cypermethrin); DYSECT?; FASTAC?; FLECTRON?; FMC? 30980; FMC 45497; FMC? 45806; FOLCORD?; IMPERATOR?; JF 5705 F?; KAFIL? SUPER; KENCIS?; NAGATA?; NRDC 149?; NRDC 160?; NRDC 166?; NURELLE; POLYTRIN?; PERMASECT C?; PP383?; PREVAIL?; RALO 10?; RIPCORD?; ROCYPER?; RYCOPEL?; SHERPA?; SIPERIN?; STOCKADE?; SUPERSECT?; TOPCLIPPARASOL?; USTAAD?; WL 43467?; WRDC149?
Biological Activity
Type II synthetic pyrethroid insecticide; an extremely potent, cell-permeable inhibitor of calcineurin.
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
Pyrethroid insecticide used to control
pests on cotton, fruit, and vegetable crops. Also used in
commercial and residential settings, ships, laboratories, and
food-processing plants. A United States Environmental
Protection Agency Restricted Use Pesticide (RUP).
Environmental Fate
Soil. The major soil metabolite was reported to be 3-phenoxybenzoic acid (Hartley and Kidd, 1987).The typical half-life of cypermethrin in the soil is 30 days, although it can range from two to eight weeks (6, 9). Soil microbes rapidly break down cypermethrin.Cypermethrin has an extremely low potential to move in the soil. It is unlikely to contaminate groundwater because it binds tightly to soil particles. Cypermethrin is stable in sunlight.The average half-life of cypermethrin on foliage is 5 days.United States Environmental Protection Agency. (1989). Cypermethrin Pesticide Fact Sheet. Washington, D.C.Knisel, W.G. (Ed.). (1993). Groundwater Loading Effects of Agricultural Management Systems. (Version 2.10). [Online]. Tifton, Georgia: United States Department of AgricultureAgricultural Research Service. [Online]. http://www.arsusda.gov/ rsml/ppdb.html
Metabolic pathway
In cabbage plants, (1R)-cis- and (1R)-trans-isomers of
cypermethrin undergo epimerization to (1S)-isomers,
cis=trans isomerization, ester bond cleavage,
hydroxylation of the phenoxy group in the alcohol
moiety or the geminal methyl group in the acid moiety,
hydration of the cyano group to an amido group with
subsequent hydrolysis to the carboxylic acid, and the
conjugation of the carboxylic acid, and alcohols with
sugars.
Shipping
UN3349 Pyrethroid pesticide, solid toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3352
Pyrethroid pesticide, liquid toxic, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
Degradation
Zeta-cypermethrin is stable as a solid but it is readily hydrolysed at
alkaline pH. Its half-lives at pH values 7 and 9 (25 °C) were 188-635 and
3 days (PM). By analogy with cypermethrin, the major products should
be 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylica cid (2,
DCVA), 3-phenoxybenzaldehyde (9, 3PBAl) and a-carbamoyl-3-
phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(the amide 3); minor products expected are the a-carboxy analogue of
3 (4) and 3-phenoxybenzoic acid (10,3PBA) (see cypermethrin, Schemes
la and lb).
Photodecomposition would be expected to be similar to that of cypermethrin.
In aqueous solution the DTSo was reported to be 20-36 days
(PM).
Toxicity evaluation
Acute oral LD50 for rats: 250-4,150 mg/kg (pure); 7,180
mg/kg (technical grade)
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
Incineration 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 40
CFR 165, follow recommendations for the disposal of pes-
ticides and pesticide containers.
Check Digit Verification of cas no
The CAS Registry Mumber 52315-07-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,3,1 and 5 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 52315-07:
(7*5)+(6*2)+(5*3)+(4*1)+(3*5)+(2*0)+(1*7)=88
88 % 10 = 8
So 52315-07-8 is a valid CAS Registry Number.
InChI:InChI=1/2C22H19Cl2NO3/c2*1-22(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/h2*3-12,17-18,20H,1-2H3/t2*17-,18-,20+/m10/s1
52315-07-8Relevant articles and documents
Preparation method of cyanogen chrysanthemum ester insecticide
-
Paragraph 0023; 0026, (2017/08/25)
The invention discloses a preparation method of a Clocythrin pesticide. The method comprises the following steps: a) mixing chrysanthemic acid and chrysanthemyl chloride and placing the mixture into a reaction vessel, adding triethylamine and introducing phosgene, slowly heating to 55-110 DEG C and fully reacting for 1-4 h so as to generate Chrysanthemoyl chloride; and b) dissolving sodium cyanide in an aqueous-phase Triton micellar solution, adding a catalyst and heating to 40 DEG C, slowly and dropwise adding mixed liquor of Chrysanthemoyl chloride and m-Phenoxybenzaldehyde, keeping the temperature and reacting for 1-4 h, cooling to 10 DEG C, adding a few amount of water and crystal seed, fully stirring and precipitating solids, and washing the precipitated solids with alkali, washing, filtering and drying so as to obtain a final product Clocythrin. The solvent in the invention can be recycled, use of the catalyst and water is reduced, and discharge of toxic wastewater and exhaust gas is minimized. The post-processing procedure is simple, and extraction and solvent distillation are not required. The final product can be obtained through simple centrifugation, washing and filtration. Discharge of solid wastes is decreased.
A new phase transfer catalyst and its applications in organic transformations
Reddy, Ch. Venkateshwar,Mahesh,Raju,Reddy, V.V. Narayana
, p. 2797 - 2802 (2007/10/03)
A new quaternary ammonium bromide salt has been used for the first time in phase transfer catalysis (PTC) reactions such as oxidation of alcohols to carbonyl compounds, alkylation and esterification reactions. Improved yields and reduced reaction times have been achieved by this procedure.
Method to diagnose metabolic pyrethroid insecticide resistance
-
, (2008/06/13)
The phenoxybenzyl moiety of conventional pyrethroids is a major site of oxidative metabolism in resistant tobacco budworms, Heliothis virescens (F.). This group was replaced with several P450 monooxygenase-inhibiting or oxidatively blocked groups. Several isomers were tested as insecticides or synergists for insecticides against tobacco budworms that were insecticide-susceptible or that expressed metabolic resistance to cypermethrin. Several compounds with insecticidal and synergistic activities were found. Activity was dependent on both geometric and stereochemical configurations. These compounds may be used in diagnosing the mechanism of resistance in field strains with acquired resistance to pyrethroids. Knowledge of the mechanism underlying acquired insecticide resistance helps farmers to control emerging resistant strains. -GOVT PAR This development of this invention was partially supported by the Government under HATCH finding awarded by the Department of Agriculture to contractor Louisiana State University Agricultural Center. The Government has certain rights in this invention.
Fungicidal active compound combinations
-
, (2008/06/13)
The present application relates to new active compound combinations composed, on the one hand, of prior art compounds metaconazole, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol and imidacloprid, 1-[(6-chloro-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazole-2-amine, and, on the other hand, of other prior-art active compounds, the combinations being extremely suitable for the protection of wood products.
Anti-fouling compositions
-
, (2008/06/13)
An anti-fouling composition comprising a carrier, and a binder, the improvement which comprises an effective amount of at least one insecticide. The composition is applied to the surfaces of articles which come into contact with seawater or brackish water, especially wood. Other conventional anti-fouling agents may also be present.
Para-hydroxyphenylacetic acid for reducing the repellency of insecticides
-
, (2008/06/13)
The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.
Methods and agents for combating cockroaches
-
, (2008/06/13)
The present invention relates to the use of compounds of the general formula I STR1 in which R1 represents C1 -C5 -alkyl or hydroxy-C1 -C5 -alkyl; R2 represents C1 -C5 -alkyl; and m represents an integer from 10 to 20, for combating cockroaches.
Conversion of pyrethroid isomers to move active species
-
, (2008/06/13)
Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl (C1 -C5) ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano (3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate in the more active species.
Preparation of alpha-cyanobenzyl esters
-
, (2008/06/13)
A process for the preparation of α-cyanobenzyl esters of cyclopropane carboxylic acids and substituted alkanoic acids by treating a carboxylic acid and a benzaldehyde with a metal cyanide, followed by treatment with a sulfonyl halide.
