| Identification | More | [Name]
Cyphenothrin | [CAS]
39515-40-7 | [Synonyms]
alpha-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CYPHENOTHRIN
D-CYPHENOTHRIN
D-TRANS-CYPHENOTHRIN
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicacicyano(3-phe
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicacicyano(3-phenoxyphenyl)methylester
Cyano-3-Phenoxybenzyl2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
Cyclopropanecarboxylicacid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,cyano(3-phenoxyphenyl)methylester
gokilaht
noxyphenyl)methylester
RS-alpha-cyano-3-phenoxybenzyl(1R)-cis,trans-crysanthemate
s2703
s2703forte
sp2703
CYPHENOTHRIN MIXTURE OF CIS AND TRANS IS
CYPHENOTHRIN (CIS+ TRANS)
α-Cyano-3-phenoxybenzyl [1R]-cis,trans-chrysanthemate
TRANSCYPHENOTHRIN
CISCYPHENOTHRIN
ALPHA-Cyano-3-phenoxybenzyl-2,2-dimethyl-3-(2-methylprop-1-enyl)-cyclopropa | [EINECS(EC#)]
254-484-5 | [Molecular Formula]
C24H25NO3 | [MDL Number]
MFCD01960864 | [Molecular Weight]
375.46 | [MOL File]
39515-40-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Thick, yellow liquid. | [Melting point ]
25°C | [Boiling point ]
504.24°C (rough estimate) | [density ]
d2525 1.083 | [vapor pressure ]
1.2×10-4pa 20°C | [refractive index ]
1.5614 (estimate) | [storage temp. ]
-20°C | [solubility ]
Chloroform, DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [Water Solubility ]
0.001 mg l-1 (23 °C) | [Merck ]
13,2797 | [Stability:]
Light Sensitive | [InChI]
1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3 | [InChIKey]
FJDPATXIBIBRIM-UHFFFAOYSA-N | [SMILES]
C\C(C)=C\C1C(C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2)C1(C)C | [CAS DataBase Reference]
39515-40-7(CAS DataBase Reference) | [EPA Substance Registry System]
39515-40-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2810 | [WGK Germany ]
3 | [RTECS ]
GZ1453500 | [HS Code ]
29269090 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1 | [Hazardous Substances Data]
39515-40-7(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Potential Exposure]
Pyrethroid insecticide. Those involved in
the manufacture and application of this agricultural chemical. | [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. UN3082 Environmentally
hazardous substances, liquid, n.o.s., Hazard class: 9;
Labels: 9-Miscellaneous hazardous material, Technical
Name Required | [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 | [Description]
Cyphenothrin is a pyrethroid insecticide with public health and industrial applications. It has a low aqueous solubility and is non-volatile. Whilst it is not expected to be persistent in soil systems, it may be persistent in water systems depending on local conditions. Based on its physico-chemical properties it is not expected to leach to groundwaters. It is highly toxic to aquatic life and moderately toxic to honeybees. Cyphenothrin is also moderately toxic to mammals via the oral route. | [Chemical Properties]
Thick, yellow liquid. | [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
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. Noncombustible con-
tainers should be crushed and buried under more than
40 cm of soil
. | [Uses]
Cyphenothrin controls insects in household, public health and
industrial situations. It is also used to control insects which attack wood
and fabrics. | [Uses]
Insecticide. | [Definition]
ChEBI: Cyphenothrin is a cyclopropanecarboxylate ester. It has a role as a pyrethroid ester insecticide and an agrochemical. It is functionally related to a chrysanthemic acid. | [Production Methods]
Cyphenothrin is commercially produced via a process that begins with the preparation of (1R,S)-trans-chrysanthemic acid through esterification of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic with thionyl chloride, followed by resolution of the (1R)-trans isomer using (S)-alpha-methylbenzylamine. The key coupling occurs via transesterification with 3-phenoxybenzyl alcohol (or its cyanohydrin variant for the alpha-cyano form) under basic conditions to form the ester linkage. Final purification by high-vacuum fractional distillation or crystallisation from hexane yields cyphenothrin. | [Mechanism of action]
Non-systemic, rapid knockdown with contact and stomach action damaging insects nervous system. Sodium channel modulator. | [Metabolic pathway]
Cyphenothrin is the name given to the α-RS,1RS-cis-trans isomer mixture
(racemic). The product now used is cyphenothrin which is 95% 1R and
75% trans. It has no field use because the chrysanthemate moiety is very
sensitive to photodegradation. A study in rodents has been reported.
Cyphenothrin is degraded mainly by photo-oxidation and by hydrolysis
and oxidation in plants and animals. | [Degradation]
Cyphenothrin is stable under normal storage conditions but it is labile
to base, being hydrolysed to trans-2,2-dimethyl-3-(2-methylprop-1-enyl)-
cyclopropanecarboxylic acid (2,trans-chrysanthemic acid) and 3-phenoxybenzaldehyde
(3, 3PBAl) and cyanide ion (Scheme 1). It is sensitive to
light (see phenothrin for expected products). | [Pesticide Type]
Insecticide |
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