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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26O3
Molecular Weight 338.44
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIORESMETHRIN

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C

InChI

InChIKey=VEMKTZHHVJILDY-UXHICEINSA-N
InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20+/m1/s1

HIDE SMILES / InChI
Molecular Formula C22H26O3
Molecular Weight 338.44
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Bioresmethrin is a synthetic pyrethroid insecticide. It is the (+)-trans isomer of resmethrin which itself contains a minimum of 30% bioresmethrin. Bioresmethrin is the [1R, trans] isomer of resmethrin and has greater insecticidal activity than the racemic mixture. Bioresmethrin is a potent contact insecticide effective against a wide range of household insects, plant pests, grain pests and insects found in animal housing. It exhibits a high order of insecticidal activity, which when coupled with its excellent toxicological properties, makes it potentially one of the safest and most useful insecticides now being produced.

CNS Activity

CNS Active
3913
Curator's Comment: As for every type I pyrethroid, bioresmethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli.

Originator

Elliott, M.
2
Curator's Comment: Bioresmethrin was discovered in England by M. Elliott and co-workers at the Rothamsted Experimental Station in collaboration with the National Research and Development Corporation (NRDC).

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002 Dec
Pyrethroid stimulation of ion transport across frog skin.
2003 Jun
Patents

Patents

JP4673837B2
32

Sample Use Guides

In Vivo Use Guide
2 groups each of 3 rats received i.v. injections into the lateral tail vein of 2.5 mg/kg ([U-14C]phenyl, 2uCi/rat) cismethrin or bioresmethrin as a solution in glycerin formal (3.75 mg/ml).
Route of Administration: Intravenous
In Vitro Use Guide
Glial cells in the ganglia and ventral connectives of Periplaneta americana treated with 5 uM bioresmethrin were found to be swollen and even more electron lucent than the control cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:57:22 GMT 2023
Edited
by admin
on Sat Dec 16 16:57:22 GMT 2023
Record UNII
YPP8YQZ13B
Record Status Validated (UNII)
Record Version
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Name Type Language
BIORESMETHRIN
INCI   INN   ISO   MI  
INCI   INN  
Official Name English
bioresmethrin [INN]
Common Name English
BIORESMETHRIN [ISO]
Common Name English
(5-BENZYL-3-FURYL)METHYL (+)-TRANS-2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE
Systematic Name English
BIORESMETHRIN [INCI]
Common Name English
RESMETHRIN (+)-TRANS-FORM [MI]
Common Name English
BIORESMETHRIN [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 97802
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
NCI_THESAURUS C737
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2034382
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
INN
5210
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106605
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
MERCK INDEX
m9544
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
MERCK INDEX
m2505
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
249-014-0
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
FDA UNII
YPP8YQZ13B
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
PUBCHEM
162381
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
EVMPD
SUB05840MIG
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
NCI_THESAURUS
C74338
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
SMS_ID
100000085889
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
ALANWOOD
bioresmethrin
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
CAS
28434-01-7
Created by admin on Sat Dec 16 16:57:22 GMT 2023 , Edited by admin on Sat Dec 16 16:57:22 GMT 2023
PRIMARY
Related Record Type Details
Structure of BIORESMETHRIN
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