| Identification | Back Directory | [Name]
Cymperator | [CAS]
52315-07-8 | [Synonyms]
POR
FURY
CCN52
AUZAR
ardap
cnn52
cypor
cyrux
demon
fenom
yt305
toppel
ustaad
wl8517
nurele
sherpa
dysect
fastac
ARRIVO
pp 383
CYNOFF
folcord
Fendona
CYMBUSH
RIPCORD
ectopor
exp5598
chinmix
ambushc
siperin
ru27998
rycopel
sf06646
jf5705f
nrdc160
nrdc166
wrdc149
wl43467
AMMO(R)
vucht424
fmc45497
fmc45806
flectron
Cypermar
Polytrin
NRDC 149
BESTOX(R)
cypercare
CYPERKILL
FASTAC(R)
FMC 30980
IMPERATOR
BASATHRIN
Afrothrin
Barricard
AGROTRINA
agrothrin
cypersect
ALFOXYLATE
hilcyperin
kalifsuper
Ripcord[R]
FLOCORD(R)
FENDONA(R)
DOMINEX(R)
cymbush 2e
Cymbush 3E
CYMPERATOR
Cypercopal
RENEGADE(R)
Kefil Super
KAFIL SUPER
CYPERMETHRI
CYPEMETHRIM
CYPERMETRIN
Supermethrin
CYPERMETHRIN
BARRICIDE(R)
cypermetryna
CiperMethrin
cypermethrine
antiborer3767
necarboxylate
alphamethrine
topclipparasol
ALPHAMETHRIN(R)
CYPERMETHRIN 90
aphacypermethrin
CIS-CYPERMETHRIN
ZETA-CYPERMETHRIN
supercypermethrin
cypermethrin-25ec
beta-Cypermethrin
cypermethrin(zeta)
CYPERMETHRIN 95%TC
opropanecarboxylate
yphenyl)methylester
Cypermethrin, solid
yphenyl)-methylester
cypermethrin solution
Cypermethrin Standard
supercypermethrinforte
barricade(insecticide)
Cypermethrin W.P. (10%)
Cypermethrin (technical)
CYPERMETHRIN, 100MG, NEAT
(1r,alpha-s)-cis-cypermethrin
Cypermethrin Solution, 100ppm
imethylcyclopropanecarboxylate
dimethylcyclopropanecarboxylate
CYPERMETHRIN, MIXTURE OF ISOMERS
NADPH--cytochrome P450 reductase
Cypermethrin 100mg [52315-07-8]
cypermethrin (bsi,e-iso,ansi,ban)
zeta-Cypermethrin 250mg [52315-07-8]
CYPERMETHRIN (MIXTURE OF ISOMERS), PESTA
cypermethrin(stereochemistryunspecified)
ANTI-P450R (CENTER) antibody produced in rabbit
CYANO(3-PHENOXYPHENYL)METHYL3-(2,2-DICHLOROETHENYL)-2,2-.
CYANO(3-PHENOXYPHENYL)METHYL3-(2,2-DICHLOROETHYENYL)-2,2.
CYANO (3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL
3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanecarboxylicacicyano(3-phe
(+-)-alpha-cyano-3-phenoxybenzyl-(+-)-cis,trans-3-(2,2-dichlorovinyl)-2,2-d
2-dichloroethenyl)-2,2-dimethylcycloptopane-cyano(3-phenoxyphenyl)methyl3-(
trans-3-(2,2-dichloroethenyl)-2,2-(rs)-cyano(3-phenoxyphenyl)methyl(1rs)-ci
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacidcyano(3-phenox
(+-)-alpha-cyano-3-phenoxybenzyl2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropa
(cyano(3-phenoxyphenyl)methyl3-(2,2-dichlorovinyl-2,2-dimethylcyclopropanecar
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid,cyano(3-phenox
(rs)-alpha-cyano-3-phenoxybenzyl(1rs)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dim
(+)alpha-cyano-3-phenoxybenzyl-(+)cis,trans-2,2-dichlorovinyl-2,2-dimethylcycl
a-cyan-3-phenoxybenzyl-3-(2,2-dichloorvinyl)-2.2-dimethylcyclopropanecarbonate
cyano-3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
Cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Alpha-cyano-3-phenoxy-benzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
α-Cyano-(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(R,S)-ALPHA-CYANO-3-PHENOXYBENZYL-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACIDYANO(3-PHENOXYPHENYL)METHYL ESTER
3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylicacid,cyano(3-phenoxy-phenyl)methylester
Cyclopropanecarboxylicacid,3-(2,2-dichloroethenyl)-2,2-dimethyl-,cyano(3-phenoxyphenyl)methylester
3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID CYANO(3-PHENOXYPHENYL)METHYL ESTER
(RS)-ALPHA-CYANO-3-PHENOXYBENZYL(1RS,3RS:1RS,3SR)-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARB
Cyano(3-phenoxyphenyl)methyl (+/-)-cis/trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
(+/-)(A)-CYANO-3-PHENOXYBENZYL (+) CIS-TRANS-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-CYCLOPROPANE CARBOXYLATE
（RS）-α-cyano-3-phenoxybenzyl (1R,S)-cis, trans-3-(2,2-dichlorovinyl0-2,2-dimethyl-cyclopropanecarboxylate
(RS)-alpha-Cyano-3-Phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(+/-)-alpha-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
[1A(S(R)),3A]-(+/-)-CYANO-(3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLATE
(RS)-ALPHA-CYANO-3-PHENOXYBENZYL(1RS,3RS)-(1RS,3SR)-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
(R,S)-.alpha.-Cyano-3-phenoxybenzyl(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Cypermethrin,α-Cyano-(3-phenoxy-phenyl)-methyl 3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclo-pro-pane-carboxylate
Alphamethrine,α-Cyano-(3-phenoxy-phenyl)-methyl 3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclo-pro-pane-carboxylate
cypermethrin cis/trans +/- 40/60 (RS)-α-cyano-3-phenoxybenzyl (1RS,3RS1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
cypermethrin cis/trans +/- 80/20 (RS)-α-cyano-3-phenoxybenzyl (1RS 3RS 1RS, 3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
1:1 mixture of (R)-alpha-Cyano(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate and (S)-alpha-Cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate | [EINECS(EC#)]
257-842-9 | [Molecular Formula]
C22H19Cl2NO3 | [MDL Number]
MFCD00055328 | [MOL File]
52315-07-8.mol | [Molecular Weight]
416.3 |
| Chemical Properties | Back Directory | [Appearance]
Thick, yellow-brown liquid or semisolid mass
(technical product). | [Melting point ]
60-80°C | [Boiling point ]
170-195°C | [density ]
1.12 | [vapor pressure ]
2.5×10-7 Pa (20 °C) | [refractive index ]
n20/D 1.57 | [Fp ]
100 °C | [storage temp. ]
−20°C
| [solubility ]
Chloroform: Slightly Soluble,Methanol: Slightly Soluble | [form ]
Viscous Liquid | [color ]
Brown | [Specific Gravity]
1.23 (20℃) | [Stability:]
Stable. Incompatible with bases, strong oxidizing agents. | [Water Solubility ]
insoluble | [BRN ]
8444118 | [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. | [EPA Substance Registry System]
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2, 2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester(52315-07-8) |
| Hazard Information | Back Directory | [Chemical Properties]
Viscous Semisolid | [Uses]
A potent inhibitor of calcineurin | [Uses]
Synthetic pyrethroid insecticide, usually exists as a mixture of cis and trans isomers. Ectoparasiticide | [Definition]
ChEBI: A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile. | [Biological Activity]
Type II synthetic pyrethroid insecticide; an extremely potent, cell-permeable inhibitor of calcineurin. | [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). | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if
breathing has stopped, and CPR if heart action has stopped.
Transfer promptly to a medical facility. When this chemical
has been swallowed, get medical attention. Do not induce
vomiting when formulations containing petroleum solvents
are ingested. Otherwise, give large quantities of water and
induce vomiting. Do not make an unconscious person
vomit. | [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. | [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. | [Agricultural Uses]
Insecticide: A U.S. EPA restricted Use Pesticide (RUP) used to control a variety of insects on cotton, fruit and vegetable crops. Also used in commercial and residential settings, ships, laboratories and food processing plants. | [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® | [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. | [storage]
+4°C | [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) |
| Questions And Answer | Back Directory | [Description]
Cypermethrin is a synthetic pyrethroid derivative of natural pyrethrins with a good insecticidal action. In vertebrates and invertebrates, cypermethrin acts mainly on the nervous system. It is both a stomach poison and a contact insecticide.
Cypermethrin is used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. Cypermethrin is used to control pests in soybean, leeks, onions, carrots, turnips, swedes, parsnips, viola spp., spinach, black currant, gooseberries, sunflowers, linseeds, groundnuts, barley, and mushrooms.
| [Uses]
Cypermethrin is a synthetic pyrethroid which is highly used pesticide in agriculture, household and animal husbandry mainly to crack, crevice and spot treatment for control of insects.
Cypermethrin is commonly used to kill household insect pests. In California, it is the fourth most commonly-used insecticide: only chlorpyrifos, pyrethrins, and diazinon have more reported applications.
It is also used in agriculture to control cotton, fruit and vegetable pests. About 90% of cypermethrin is manufactured for cotton crops (WHO, 1998). | [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
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