EPOXICONAZOLE

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Source Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...

Structure

InChI Key ZMYFCFLJBGAQRS-IRXDYDNUSA-N
Smiles Fc1ccc(cc1)[C@]2(Cn3cncn3)O[C@H]2c4ccccc4Cl
InChI
InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2/t16-,17-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H13ClFN3O
Molecular Weight 329.76
AlogP 3.43
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 43.24
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 23.0
Assay Description Organism Bioactivity Reference
Selectivity ratio of relative toxicity against po dosed rat to relative efficacy against Gibberella zeae None 0.0
Toxicity in po dosed Rattus norvegicus (rat) relative to metconazole Rattus norvegicus 0.19
Antifungal activity against Fusarium graminearum after 8 hr by microscopic analysis relative to prothioconazole Fusarium graminearum 0.0
Growth inhibition of Fusarium graminearum isolate 74B at 10'-4 M after 14 days Fusarium graminearum 95.7 %
Growth inhibition of Fusarium graminearum isolate 137 at 10'-4 M after 14 days Fusarium graminearum 99.6 %
Growth inhibition of Fusarium graminearum isolate 4527b at 10'-4 M after 14 days Fusarium graminearum 98.0 %
Growth inhibition of Fusarium graminearum isolate 123 at 10'-4 M after 14 days Fusarium graminearum 95.9 %
Growth inhibition of Fusarium graminearum isolate 102 at 10'-4 M after 14 days Fusarium graminearum 97.1 %
Growth inhibition of Fusarium graminearum isolate 106 at 10'-4 M after 14 days Fusarium graminearum 95.4 %
Growth inhibition of Fusarium graminearum isolate 37 at 10'-4 M after 14 days Fusarium graminearum 98.7 %
Antifungal activity against Fusarium graminearum isolate 137 after 8 hr by microscopic analysis Fusarium graminearum 10800000.0 nM
Antifungal activity against Fusarium graminearum isolate 106 after 8 hr by microscopic analysis Fusarium graminearum 10800000.0 nM
Antifungal activity against Fusarium graminearum isolate 123 after 8 hr by microscopic analysis Fusarium graminearum 10800000.0 nM
Antifungal activity against Fusarium graminearum isolate 102 after 8 hr by microscopic analysis Fusarium graminearum 10800000.0 nM
Antifungal activity against Fusarium graminearum isolate 37 after 8 hr by microscopic analysis Fusarium graminearum 10800000.0 nM
Toxicity in po dosed Rattus norvegicus (rat) Rattus norvegicus 3160.0 mg.kg-1
Aqueous solubility of the compound assessed per 100 g None 0.7 mg
Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR2 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay Oculimacula yallundae 3.0
Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR1 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay Oculimacula yallundae 2.0
Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR2 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by mycelial growth inhibition assay Oculimacula yallundae 5.0
Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR1 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by mycelial growth inhibition assay Oculimacula yallundae 3.3
Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr Oculimacula yallundae 0.3 ug.mL-1
Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks Oculimacula yallundae 0.3 ug.mL-1
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay Oculimacula yallundae 5.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay Oculimacula yallundae 150.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay Oculimacula yallundae 2.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay Oculimacula yallundae 60.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay Oculimacula yallundae 30.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by mycelial growth inhibition assay Oculimacula yallundae 2.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay Oculimacula yallundae 3.3
Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae in presence of 10 g glucose by mycelial growth inhibition assay None 2.0
Fungicidal activity against Oculimacula yallundae assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks Oculimacula yallundae 0.15 ug.mL-1
Fungicidal activity against Oculimacula acuformis assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks Oculimacula acuformis 0.3 ug.mL-1
Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae by germ tube elongation inhibition assay None 15.0
Fungicidal activity against Oculimacula yallundae assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr Oculimacula yallundae 0.02 ug.mL-1
Fungicidal activity against Oculimacula acuformis assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr Oculimacula acuformis 0.3 ug.mL-1
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay Oculimacula yallundae 3.3
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by mycelial growth inhibition assay Oculimacula yallundae 1.0
Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay Oculimacula yallundae 6.7
Fungicidal activity against Zymoseptoria tritici isolate TAG74-3 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at doses > 1/16 recommended field rate measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate OP7 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at doses > 1/16 recommended field rate measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate TAG74-3 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as pycnidia formation at doses > 1/16 recommended field rate measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate OP7 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as pycnidia formation at doses > 1/16 recommended field rate measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate TAG74-3 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as pycnidia formation at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate OP7 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as pycnidia formation at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici None
Fungicidal activity against Zymoseptoria tritici isolate R10-13 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici 400.0 pg
Fungicidal activity against Zymoseptoria tritici isolate OP6 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici 14.0 pg
Fungicidal activity against Zymoseptoria tritici isolate TAG74-3 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici 9284.0 pg
Fungicidal activity against Zymoseptoria tritici isolate OP7 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations inoculated on compound pre-treated wheat cultivar Riband seedlings assessed as fungal DNA level at 39.06 ppm measured 21 days post fungal inoculation Zymoseptoria tritici 1600.0 pg
Fungicidal activity against Zymoseptoria tritici isolate TAG74-3 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 1.41 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate OP7 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.819 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate TAG1-18 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.911 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate V18 with 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.759 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate OP6 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.085 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate R10-13 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.091 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate R03-54 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.092 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate R03-29 without 120 bp insertion expressing CYP51 variant with combination of L50S, S188N, I381V, deltaY459/G460 and N513K mutations assessed as fungal growth inhibition Zymoseptoria tritici 0.067 ug.mL-1
Fungicidal activity against Zymoseptoria tritici isolate IPO323 without 120 bp insertion expressing wild type CYP51 assessed as fungal growth inhibition Zymoseptoria tritici 0.0015 ug.mL-1

Cross References

Resources Reference
ChEMBL CHEMBL486029
PubChem 11759286
SureChEMBL SCHEMBL1441374
ZINC ZINC00967738
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