Spirodiclofen
Spirodiclofen is an organochlorine acaricide, a dichlorobenzene, an oxaspiro compound and a gamma-lactone. It derives from a 1,3-dichlorobenzene || CCE04 = T1JSJ6 (corrected with insertion). Overexpression of an alternative allele of carboxyl/choline esterase 4 (CCE04) of Tetranychus urticae is associated with high levels of resistance to the keto-enol acaricide spirodiclofen through sequestration. Hydrolysis of the ester bond gives the spirodiclofen enol which is the active compoud. Spirodiclofen is hydrolysed by CYP39E10 in mites. The ester bond is hydrolysed by esterases in plasma and liver of vertebrates. (Wei et al. 2019
General
Type : Organochlorine,Acaricide
Chemical_Nomenclature : [3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl] 2,2-dimethylbutanoate
Canonical SMILES : CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl
InChI : InChI=1S\/C21H24Cl2O4\/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21\/h8-9,12H,4-7,10-11H2,1-3H3
InChIKey : DTDSAWVUFPGDMX-UHFFFAOYSA-N
Other name(s) : UNII-3X7G31F5MX,3X7G31F5MX,CHEBI:38639,ZINC2540062,SCHEMBL27234,CHEMBL2227839,Butanoic acid, 2,2-dimethyl-, 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro(4.5)dec-3-en-4-yl ester
MW : 411.3
Formula : C21H24Cl2O4
CAS_number : 148477-71-8
PubChem : 177863
UniChem : DTDSAWVUFPGDMX-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
Families : Spirodiclofen ligand of proteins in family: Cholinesterase-like
Stucture :
Protein : tetur-t1jsj6
References (3)
| Title : Overexpression of an alternative allele of carboxyl\/choline esterase 4 (CCE04) of Tetranychus urticae is associated with high levels of resistance to the keto-enol acaricide spirodiclofen - Wei_2020_Pest.Manag.Sci_76_1142 |
| Author(s) : Wei P , Demaeght P , De Schutter K , Grigoraki L , Labropoulou V , Riga M , Vontas J , Nauen R , Dermauw W , Van Leeuwen T |
| Ref : Pest Manag Sci , 76 :1142 , 2020 |
| Abstract : Wei_2020_Pest.Manag.Sci_76_1142 |
| ESTHER : Wei_2020_Pest.Manag.Sci_76_1142 |
| PubMedSearch : Wei_2020_Pest.Manag.Sci_76_1142 |
| PubMedID: 31583806 |
| Gene_locus related to this paper: tetur-t1jsj6 , tetur-t1jth6 |
| Title : Transcriptome profiling of a spirodiclofen susceptible and resistant strain of the European red mite Panonychus ulmi using strand-specific RNA-seq - Bajda_2015_BMC.Genomics_16_974 |
| Author(s) : Bajda S , Dermauw W , Greenhalgh R , Nauen R , Tirry L , Clark RM , Van Leeuwen T |
| Ref : BMC Genomics , 16 :974 , 2015 |
| Abstract : Bajda_2015_BMC.Genomics_16_974 |
| ESTHER : Bajda_2015_BMC.Genomics_16_974 |
| PubMedSearch : Bajda_2015_BMC.Genomics_16_974 |
| PubMedID: 26581334 |
| Title : Molecular analysis of resistance to acaricidal spirocyclic tetronic acids in Tetranychus urticae: CYP392E10 metabolizes spirodiclofen, but not its corresponding enol - Demaeght_2013_Insect.Biochem.Mol.Biol_43_544 |
| Author(s) : Demaeght P , Dermauw W , Tsakireli D , Khajehali J , Nauen R , Tirry L , Vontas J , Lummen P , Van Leeuwen T |
| Ref : Insect Biochemistry & Molecular Biology , 43 :544 , 2013 |
| Abstract : Demaeght_2013_Insect.Biochem.Mol.Biol_43_544 |
| ESTHER : Demaeght_2013_Insect.Biochem.Mol.Biol_43_544 |
| PubMedSearch : Demaeght_2013_Insect.Biochem.Mol.Biol_43_544 |
| PubMedID: 23523619 |