| Identification | Back Directory | [Name]
S-Bioallethrin | [CAS]
28434-00-6 | [Synonyms]
ESBIOL
ru16121
Allthrin
ESBIOL(R)
ai3-29024
esbiothirn
D-ALLETHRIN
PYRESYN(TM)
waspkillerii
BIOALLETHRIN
d-t-allethrin
esbioallethrin
S-BIOALLETHRIN
ESDEPALLETHRINE
(+)-trans-allethrin
trans-(+)-allethrin
s-trans-bioallethrin
D-TRANS BIOALLETHRIN
esbiolconcentrate90%
(+)-trans-(S)-allethrin
S-BIOALLETHRIN, 250MG, NEAT
bioallethrin(non-specificname)
d-allethrolonechrysanthemumate
S-Bioallethrin @100 μg/mL in MeOH
S-Bioallethrin
Solution, 1000ppm
d-allethroloned-trans-chrysanthemate
d-allethronyld-trans-chrysanthemumate
d-allylrethronyld-trans-chrysanthemate
ESBIOL PESTANAL, 250 MG (S-BIOALLETHRINE
(+)-allethronyl(+)-trans-chrysanthemumate
D-TRANS-CHRYSANTHEMUM-MONOCARBOXYLIC ACID ESTER
S-Bioallethrin solution in Acetonitrile, 100μg/mL
D-2-ALLYL-4-HYDROXY-3-METHYL-2-CYCLOPENTENE-1-ONE
rwith(+)-2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one
(S)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl (1R)-trans-chrysanthemate
(1s)-3-allyl-2-methyl-4-oxocyclopent-2-enyl-(1r)-trans-chrysanthemate
D-TRANS-2,2-DIMETHYL-3[2-METHYLPROPENYL] CYCLOPROPANECARBOXYLIC ACID ESTER
2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylicaci(+)-(e)-cyclopropanecarboxylicacieste
D-2-ALLYL-4-HYDROXY-3-METHYL-2-CYCLOPENTENE-1-ONE, D-TRANS CHRYSANTHEMUMMONOCARBOXYLIC ACID ESTER
(S)-3-ALLYL-2-METHYL-4-OXOCYCLOPENT-2-ENYL-(1R,3R)-2,2-DIMETHYL3-(METHYLPROP-1-ENYL)CYCLOPROPANE CARBOXYLATE
2-Methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
S-3-ALLYL-2-METHYL-4-OXOCYCLOPENT-2-ENYL-(1R,3R)-2,2-DIMETHYL-3-(2-METHYL PROP-1-ENYL)CYCLOPROPANE CARBOXYLATE
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl [1R-[1α(S*),3β]]-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
(RS)-3-ALLYL-2-METHYL-4-OXOCYCLOPENT-2-ENYL (1RS,3RS:1RS,3SR)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
(1R)-2,2-Dimethyl-3α-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1S)-3-allyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester
3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl [1R-[1alpha(S*),3beta]]-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-2-METHYL-4-OXO-3-(2-PROPENYL)2-CYCLOPENTEN-1-YL ESTER, (1R)
2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate,(1R-(1A(S*),3B))-
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3(2-METHYL-1-PROPENYL)-2-METHYL-4OXO-3-(2-PROPENYL)-2-CYCLOPENTEN-1-YL ESTER, (1R,3R)
DL-2-ALLYL-4-HYDROXY-3-METHYL-2-CYCLOPENTENE-1-ONE, D-TRANS-2,2-DIMETHYL-3[2-METHYL-PROPENYL]-CYCLOPROPANECARBOXYLIC ACID ESTER
3-Allyl-2-methyl-4-oxocyclopent-2-en-1-yl [1R-[1-alpha(S*),3-beta]]-2,2-dimethyl-3-(2-Methylprop-1-enyl)cyclopropanecarboxylate
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, (1R,3R)-
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1S)-2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl ester, (1R,3R)- | [EINECS(EC#)]
249-013-5 | [Molecular Formula]
C19H26O3 | [MDL Number]
MFCD00167397 | [MOL File]
28434-00-6.mol | [Molecular Weight]
302.41 |
| Chemical Properties | Back Directory | [Boiling point ]
140°C (13.33 Pa) | [density ]
1.02 | [refractive index ]
1.4200 (estimate) | [Fp ]
120 °C | [storage temp. ]
2-8°C | [solubility ]
DMSO : 100 mg/mL (330.68 mM; Need ultrasonic) | [form ]
neat | [color ]
Light yellow to yellow | [Water Solubility ]
insoluble | [Stability:]
Light Sensitive, Temperature Sensitive | [InChI]
InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3/t14-,16+,17+/m1/s1 | [InChIKey]
ZCVAOQKBXKSDMS-PVAVHDDUSA-N | [SMILES]
[C@@H]1(C(O[C@H]2CC(=O)C(CC=C)=C2C)=O)[C@@H](/C=C(/C)\C)C1(C)C | [EPA Substance Registry System]
Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1- propenyl)-, (1S)-2-methyl-4-oxo-3-(2-propenyl)- 2-cyclopenten-1-yl ester, (1R,3R)-(28434-00-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
20/22-50/53 | [Safety Statements ]
36-60-61 | [RIDADR ]
UN3082 9/PG 3 | [WGK Germany ]
3 | [RTECS ]
GZ1472000 | [HazardClass ]
6.1 | [PackingGroup ]
III | [Toxicity]
chicken,LD50,oral,> 5gm/kg (5000mg/kg),Pesticide Manual. Vol. 9, Pg. 78, 1991. |
| Hazard Information | Back Directory | [Chemical Properties]
S-Bioallethrin is a yellow liquid. It is miscible with most organic solvents. S-Bioallethrin is the ester of the (1R, trans)-acid with (1S)-allethrolone. S-bioallethrin is a synthetic pyrethroid with fast knock-down activity against household pest insects. It is several times as effective as allethrin against flying and crawling insects. It is used in public health applications against mosquitoes, houseflies and cockroaches. | [Uses]
S-Bioallethrin, by far the most potent constituent of allethrin, is a contact insecticide with rapid knockdown effect. Its effectiveness is enhanced by the addition of a synergist such as piperonyl butoxide or MGK 264 in pesticide formulations. It is used in aerosols, coils or sprays indoors against flying and crawling insects. | [Definition]
ChEBI: (+)-trans-(S)-allethrin is a (+)-trans-allethrin. It is an enantiomer of a (-)-trans-(R)-allethrin. | [Production Methods]
S-bioallethrin is produced by adapting the standard allethrin manufacturing route to deliver the biologically active S-enantiomer with high optical purity. Commercial processes begin with assembly of the chrysanthemic acid moiety from cyclopropane based precursors, followed by preparation of the allethrolone alcohol fragment through controlled allylic oxidation and rearrangement chemistry. The two components are then coupled via esterification, but with an added stereochemical control step: manufacturers either use enantioselective synthesis of the chrysanthemate portion or resolve a racemic intermediate to isolate the S-configured acid before ester formation. Final purification yields a stable technical grade ester suitable for formulation. | [General Description]
Clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin. | [Air & Water Reactions]
Insoluble in water. | [Reactivity Profile]
ALLETHRIN is incompatible with alkalis. | [Mechanism of action]
Non-systemic, contact and stomach action with a rapid knock-down effect. Sodium channel modulator. | [storage]
Store at -20°C | [Pesticide Type]
Insecticide |
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