Strobilurin O

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Category Mycotoxins
Catalog number BBF-03084
CAS
Molecular Weight 458.54
Molecular Formula C26H34O7

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Description

Strobilurin O is a compound produced by Mycena galericularata. It has nematicidal activity, strong cytotoxicity to HeLa-S3, with IC50 of 0.02-0.06 μg/mL. It also has anti-fungal activity such as Pyricularia oryzae, with MIC 12.5 μg/mL.

Specification

IUPAC Name methyl (2E,3Z,5E)-6-[3-[[(2R)-3,3-dimethyloxiran-2-yl]methoxy]-4,4-dimethyl-2,3-dihydro-1,5-benzodioxepin-7-yl]-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate
Canonical SMILES CC(=CC=CC1=CC2=C(C=C1)OCC(C(O2)(C)C)OCC3C(O3)(C)C)C(=COC)C(=O)OC
InChI InChI=1S/C26H34O7/c1-17(19(14-28-6)24(27)29-7)9-8-10-18-11-12-20-21(13-18)32-25(2,3)22(15-30-20)31-16-23-26(4,5)33-23/h8-14,22-23H,15-16H2,1-7H3/b10-8+,17-9-,19-14+/t22?,23-/m1/s1
InChI Key GQNXUZDKRRAAIW-LTPVFVFHSA-N

Properties

Appearance Colorless Oil
Antibiotic Activity Spectrum fungi; parasites
Boiling Point 588.5±50.0°C at 760 mmHg
Density 1.2±0.1 g/cm3

Reference Reading

1. Design, synthesis and biological activity of new strobilurin derivatives with a 1H-pyrazol-5-oxy side chain
Miao Li, Chang-Ling Liu, Ji-Chun Yang, Lin Li, Zhi-Nian Li, Hong Zhang, Zheng-Ming Li Nat Prod Commun. 2009 Sep;4(9):1215-20.
A series of new strobilurin derivatives with a substituted pyrazole side chain (5 and 6) were designed and synthesized. The new derivatives were synthesized from substituted phenones as starting material via esterification, cyclization and condensation reactions. All compounds were identified by 1H NMR and IR spectral and elemental analyses. Preliminary biological evaluation showed that some of the compounds had good fungicidal activity against cucumber downy mildew (CDM) and wheat powdery mildew (WPM) at 6.25 and 1.56 mg L(-1), respectively. Some of the compounds showed insecticidal activity against armyworm (AW), green peach aphid (GPA) and culex mosquitoes at 600 mg L(-1).

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