| Identification | Back Directory | [Name]
BETA-CYPERMETHRIN | [CAS]
65731-84-2 | [Synonyms]
NRDC-168S
ASYMETHRIN
Agrothrin(TM)
β-CYPERMETHRIN
Einecs 265-898-0
beta-Cypermetrin
beta-CyperMethri
Bata-cypermethrin
alpha-Cypermethrin
beta-Cypermethrin [iso]
(1R,αS)-cis-Cypermethrin
(1R-cis-αS)-Cypermethrin
(1R,2R,1'S)-Cypermethrin
(1R)-trans-(αS)-cypermethrin
Alphamethrin Solution, 1000ppm
Alphamethrin Solution in Hexane
Cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(1R,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (S)-α-cyano-3-phenoxybenzyl ester
(1R,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (αS)-α-cyano-3-phenoxybenzyl ester
(1R)-2,2-Dimethyl-3β-(2,2-dichlorovinyl)cyclopropane-1β-carboxylic acid (S)-α-cyano-3-phenoxybenzyl ester
(1R)-3β-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1β-carboxylic acid (S)-α-cyano-3-phenoxybenzyl ester
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (S)-cyano(3-phenoxyphenyl)methyl ester, (1R,3R)-
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1R-(1alpha(S*),3alpha))- | [EINECS(EC#)]
265-898-0 | [Molecular Formula]
C22H19Cl2NO3 | [MDL Number]
MFCD04112603 | [MOL File]
65731-84-2.mol | [Molecular Weight]
416.3 |
| Hazard Information | Back Directory | [Description]
A pyrethroid broad-spectrum insecticide. It has a low aqueous solubility, in relatively volatile and, based on its chemical properties, is not expected to leach to groundwater. It is non-persistent in soil systems. It is highly toxic to mammals and there is some concern regarding its ability to bioconcentrate. It is moderately toxic to birds, earthworms and highly toxic to honeybees and most aquatic species except for algae where there is a reduced risk. | [Uses]
Beta-cypermethrin is used to control a wide range of insects, especially
Lepidoptera and Coleoptera, in alfalfa, cotton, cereals, fruit, vines,
vegetables, beans, beets, tobacco, oilseed rape and other crops. It is also
used for insect control in public health and for ectoparasite control on
animals. | [Definition]
ChEBI: (1R)-cis-(alphaS)-cypermethrin is a cyclopropanecarboxylate ester. It is an enantiomer of a (1S)-cis-(alphaR)-cypermethrin. | [Production Methods]
Beta-cypermethrin is produced through a multi-step chemical synthesis that builds on the pyrethroid framework derived from chrysanthemic acid. The process begins with the preparation of key intermediates such as 3-phenoxybenzaldehyde and cyclopropane carboxylic acid derivatives. These are then reacted with cyanide compounds to introduce the cyano group, a critical feature for insecticidal activity. The final step involves esterification to form the active beta-cypermethrin isomer mixture, which includes two enantiomeric forms with enhanced potency. | [Mechanism of action]
Non-systemic with contact and stomach action. Sodium channel modulator. | [Metabolic pathway]
Beta-cypermethrin is composed of two of the four cis-cypermethrin isomers
(1RcisaS and 1ScisaR isomers) [i.e. alpha-cypermethrin] and two of
the four trans-cypermethrin isomers (1RtransaS and 1StransaR) [i.e. thetacypermethrin].
The fate of these four isomers (separately) has been
reported for soils. Metabolite analysis was conducted in enough detail to
indicate that the fate of the components was very similar to their fate
when presented to biological systems as part of cypermethrin. Thus reference
can be made to the cypermethrin entry for details. The structure and
Scheme numbering used below refers to the cypermethrin entry. | [Degradation]
Beta-cypermethrin is stable as a solid but it is epimerised in weak base
solution and readily hydrolysed at higher pH. Its half-lives at pH values
3, 7 and 9 (25 °C) were 50,40 and 15 days (PM). By analogy with cypermethrin,
the rate-determining step in dilute solution is nucleophilic attack
by OH-. Half-lives of cis-cypermethrin in river water and sea water at
25 °C were 21 and 24 days, respectively; the trans-isomer would be
expected to be more rapidly degraded. Major products were 3-(2,2-
dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (2, DCVA), 3-
phenoxybenzaldehyde (9, 3PBAl) and a-carbamoyl-3-phenoxybenzyl
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate( the amide
3); minor products were 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. | [Pesticide Type]
Insecticide; Veterinary substance |
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