Synonyms
UNII TLW21058F5
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 RIOXQFHNBCKOKP-UHFFFAOYSA-N
Smiles CCCCNC(=O)n1c(NC(=O)OC)nc2ccccc12
InChI
InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H18N4O3
Molecular Weight 290.32
AlogP 2.97
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 85.25
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
In vivo antifungal activity against Blumeria graminis f. sp. hordei infected barley seedlings assessed as control of barley powdery mildew disease development at 1 ug/ml treated 1 day before spore inoculation measured 3-7 days after inoculation Blumeria graminis f. sp. hordei 75.0 %
In vivo antifungal activity against Blumeria graminis f. sp. hordei infected barley seedlings assessed as control of barley powdery mildew disease development at 100 ug/ml treated 1 day before spore inoculation measured 3-7 days after inoculation Blumeria graminis f. sp. hordei 100.0 %
Antifungal activity against Colletotrichum gloeosporioides assessed as as appearance of diffuse zone of inhibition at 2 mM in 2 uL solution by direct bio-autography assay Colletotrichum gloeosporioides None
Antifungal activity against Colletotrichum acutatum assessed as appearance of diffuse zone of inhibition at 2 mM in 2 uL solution by direct bio-autography assay Colletotrichum acutatum None
Antifungal activity against Colletotrichum fragariae assessed as inhibition of fungal growth at 2 mM in 2 uL solution by direct bio-autography assay Colletotrichum fragariae 21.3 %
Antifungal activity against Blumeria graminis f. sp. hordei infected compound pre-treated barley plant seedlings assessed as barley powdery mildew disease control efficacy at 1 ug/mL under greenhouse conditions Blumeria graminis f. sp. hordei 90.0 %
Antifungal activity against Blumeria graminis f. sp. hordei infected compound pre-treated barley plant seedlings assessed as barley powdery mildew disease control efficacy at 100 ug/mL under greenhouse conditions Blumeria graminis f. sp. hordei 100.0 %
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as inhibition of mycelial radial growth Rhizoctonia solani AG-1 IA 17.43 mg/L Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as inhibition of mycelial radial growth Rhizoctonia solani AG-1 IA 0.352 ug.mL-1
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as mycelial radial growth at 100 mg/l (Rvb = 40 mm) Rhizoctonia solani AG-1 IA 0.0 mm
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as mycelial radial growth at 1 mg/l (Rvb = 40 mm) Rhizoctonia solani AG-1 IA 9.6 mm
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as mycelial radial growth at 10 mg/l (Rvb = 40 mm) Rhizoctonia solani AG-1 IA 0.0 mm
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as mycelial radial growth at 0.1 mg/l (Rvb = 40 mm) Rhizoctonia solani AG-1 IA 38.8 mm
Antifungal activity against Fusarium oxysporum f. sp. cubense race 4 infected in Cavendish banana plant assessed as reduction in disease severity at 25 ug a.i./ml applied as soil drench treatment 1 week after planting measured after 7 weeks in greenhouse conditions Fusarium oxysporum f. sp. cubense race 4 72.2 %
Antifungal activity against Fusarium oxysporum f. sp. cubense race 4 infected in Cavendish banana plant assessed as reduction in disease severity at 25 ug a.i./ml applied as soil drench treatment immediately after planting measured after 7 weeks in greenhouse conditions Fusarium oxysporum f. sp. cubense race 4 22.2 %
Antifungal activity against Fusarium oxysporum f. sp. cubense race 4 infected in Cavendish banana plant assessed as reduction in disease severity at 25 ug a.i./ml applied as root dip treatment for 10 min measured after 7 weeks in greenhouse conditions Fusarium oxysporum f. sp. cubense race 4 66.7 %
Phytotoxicity against Chinese Musa acuminata AAA Group (Cavendish banana) at 5 to 25 ug a.i./ml relative to control Musa acuminata AAA Group None
Growth inhibition of Fusarium oxysporum f. sp. cubense race 4 isolate CAV 031 at 100 ug/ml after 7 days Fusarium oxysporum f. sp. cubense race 4 None
Phytotoxicity against Chinese Musa acuminata AAA Group (Cavendish banana) at 50 ug a.i./ml relative to control Musa acuminata AAA Group None
Growth inhibition of Fusarium oxysporum f. sp. cubense race 4 isolate CAV 031 at 50 ug/ml after 7 days Fusarium oxysporum f. sp. cubense race 4 None
Growth inhibition of Fusarium oxysporum f. sp. cubense race 4 isolate CAV 031 at 10 ug/ml after 7 days Fusarium oxysporum f. sp. cubense race 4 None
Growth inhibition of Fusarium oxysporum f. sp. cubense race 4 isolate CAV 086 at 5 ug/ml after 7 days Fusarium oxysporum f. sp. cubense race 4 None
Fungicidal activity against Monilinia laxa isolate MLX1 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 100.0 %
Fungicidal activity against Monilinia laxa isolate MLP4 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 100.0 %
Fungicidal activity against Monilinia laxa isolate MLK12 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 100.0 %
Fungicidal activity against Monilinia laxa isolate MLK1 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 100.0 %
Fungicidal activity against Monilinia laxa isolate MLC2 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 80.01 %
Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 2 uL in 2 mM acetone by direct bioautography Colletotrichum gloeosporioides 19.33 mm
Antifungal activity against Colletotrichum acutatum assessed as growth inhibition at 2 uL in 2 mM acetone by direct bioautography Colletotrichum acutatum 18.0 mm
Fungicidal activity against Monilinia laxa isolate MLX5 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Fungicidal activity against Monilinia laxa isolate MLP2 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Fungicidal activity against Monilinia laxa isolate MLBO5 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Fungicidal activity against Monilinia laxa isolate MLBO2 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Fungicidal activity against Monilinia laxa isolate MLA1 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Fungicidal activity against Monilinia laxa isolate MLG1 assessed as mycelial growth at 1 ug/ml at 25 degC after 4 days Monilinia laxa 0.0 %
Antifungal activity against Colletotrichum fragariae assessed as growth inhibition at 2 uL in 2 mM acetone by direct bioautography Colletotrichum fragariae 18.33 mm
Antifungal activity against Penicillium italicum CECT 2294 at 0.2 ug/disk after 72 hr by paper disk-agar diffusion assay Penicillium italicum 16.67 mm
Antifungal activity against Aspergillus parasiticus CECT 2681 at 1 ug/disk after 72 hr by paper disk agar diffusion assay Aspergillus parasiticus 8.33 mm
Antifungal activity against Hypocrea rufa CECT 2423 at 1 ug/disk after 72 hr by paper disk agar diffusion assay Hypocrea rufa 12.33 mm
Antifungal activity against Trichothecium roseum CECT 2410 at 5 ug/disk after 72 hr by paper disk agar diffusion assay Trichothecium roseum 29.67 mm
Antifungal activity against Colletotrichum gloeosporioides CECT 2859 at 0.5 ug/disk after 72 hr by paper disk-agar diffusion assay Colletotrichum gloeosporioides 26.67 mm
Antifungal activity against Phytophthora citrophthora CECT 2353 at 1.5 ug/disk after 72 hr by paper disk agar diffusion assay Phytophthora citrophthora 17.13 mm
Antifungal activity against Verticillium dahliae CCM 269 at 0.25 ug/disk after 72 hr by paper disk-agar diffusion assay Verticillium dahliae 14.32 mm
Antifungal activity against Fusarium oxysporum f. sp. gladioli CCM 233 at 10 ug/disk after 72 hr by paper disk agar diffusion assay Fusarium oxysporum f. sp. gladioli 9.33 mm
Antifungal activity against Fusarium oxysporum f. sp. niveum CCM 259 at 5 ug/disk after 72 hr by paper disk-agar diffusion assay Fusarium oxysporum f. sp. niveum 17.33 mm
Antifungal activity against Fusarium culmorum CECT 2148 at 10 ug/disk after 72 hr by paper disk agar diffusion assay Fusarium culmorum 19.0 mm
Antifungal activity against Colletotrichum gloeosporioides assessed as diffuse inhibitory zone at concentration of 2 mM in volume of 2 ul of EtOH measured after 4 days by TLC based direct bioautography assay Colletotrichum gloeosporioides None
Antifungal activity against Colletotrichum fragariae assessed as size of growth inhibitory zone at concentration of 2 mM in volume of 2 ul of EtOH measured after 4 days by TLC based direct bioautography assay Colletotrichum fragariae 21.3 mm
Antifungal activity against Colletotrichum acutatum assessed as diffuse inhibitory zone at concentration of 2 mM in volume of 2 ul of EtOH measured after 4 days by TLC based direct bioautography assay Colletotrichum acutatum None
Fungicidal activity against Zymoseptoria tritici Zymoseptoria tritici 0.6 ug.mL-1
Fungicidal activity against Rhizoctonia solani Rhizoctonia solani 6.2 ug.mL-1
Fungicidal activity against Fusarium graminearum Fusarium graminearum 0.6 ug.mL-1
Fungicidal activity against Fusarium oxysporum f. sp. Lycopersici Fusarium oxysporum f. sp. lycopersici 1.5 ug.mL-1
Antifungal activity against Fusarium avenaceum VIAM MA1512 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Fusarium avenaceum 100.0 ug.mL-1 Antifungal activity against Fusarium avenaceum VIAM MA1512 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Fusarium avenaceum 200.0 ug ml-1 Antifungal activity against Fusarium avenaceum VIAM MA1512 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Fusarium avenaceum 0.02 ug.mL-1
Antifungal activity against Alternaria citri CBS 192.81; VIAM MA1628 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Alternaria citri 200.0 ug.mL-1 Antifungal activity against Alternaria citri CBS 192.81; VIAM MA1628 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Alternaria citri 200.0 ug ml-1 Antifungal activity against Alternaria citri CBS 192.81; VIAM MA1628 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Alternaria citri 200.0 ug.mL-1
Antifungal activity against Magnaporthe grisea VIAM MA1627 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Magnaporthe grisea 200.0 ug.mL-1 Antifungal activity against Magnaporthe grisea VIAM MA1627 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Magnaporthe grisea 84.0 ug ml-1 Antifungal activity against Magnaporthe grisea VIAM MA1627 assessed as inhibition of spore germination by microdilution technique linked with digital image analysis Magnaporthe grisea 0.06 ug.mL-1
Fungicidal activity against Fusarium culmorum CCM 172 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Fusarium culmorum 87.0 %
Fungicidal activity against Fusarium oxysporum f. sp. gladioli CCM 233 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Fusarium oxysporum f. sp. gladioli 11.1 %
Fungicidal activity against Fusarium oxysporum f. sp. niveum CCM 259 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Fusarium oxysporum f. sp. niveum 100.0 %
Fungicidal activity against Galactomyces geotrichum CCM 245 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Galactomyces geotrichum 0.0 %
Fungicidal activity against Colletotrichum gloeosporioides CECT 2859 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Colletotrichum gloeosporioides 100.0 %
Fungicidal activity against Colletotrichum coccodes CCM 327 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Colletotrichum coccodes 100.0 %
Fungicidal activity against Trichothecium roseum CECT 2410 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Trichothecium roseum 100.0 %
Fungicidal activity against Alternaria tenuis CECT 2662 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Alternaria tenuis 0.0 %
Fungicidal activity against Verticillium dahliae CCM 269 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 6 days Verticillium dahliae 100.0 %
Fungicidal activity against Phytophthora citrophthora assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Phytophthora citrophthora 100.0 %
Fungicidal activity against Hypocrea rufa CECT 2423 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Hypocrea rufa 100.0 %
Fungicidal activity against Penicillium italicum CECT 2294 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Penicillium italicum 100.0 %
Fungicidal activity against Aspergillus parasiticus CECT 2681 assessed as inhibition of radial mycelial growth at 2.5 ug/mL after 4 days Aspergillus parasiticus 100.0 %
Antifungal activity against Diaporthe ampelina assessed as growth inhibition at 300 uM after 120 hr by microplate photometric analysis Diaporthe ampelina 57.0 %
Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 30 to 300 uM after 120 hr by microplate photometric analysis Phomopsis obscurans None
Antifungal activity against Botryotinia fuckeliana assessed as growth inhibition at 30 to 300 uM after 48 hr by microplate photometric analysis Botryotinia fuckeliana None
Antifungal activity against Fusarium oxysporum assessed as growth inhibition at 300 uM after 48 hr by microplate photometric analysis Fusarium oxysporum 77.0 %
Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 300 uM after 48 hr by microplate photometric analysis Colletotrichum gloeosporioides 66.0 %
Antifungal activity against Colletotrichum fragariae assessed as growth inhibition at 30 to 300 uM after 48 hr by microplate photometric analysis Colletotrichum fragariae 76.0 %
Antifungal activity against Colletotrichum acutatum assessed as growth inhibition at 300 uM after 48 hr by microplate photometric analysis Colletotrichum acutatum 33.0 %
Fungicidal activity against Fusarium graminearum E198Q harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.93 ug.mL-1
Fungicidal activity against Fusarium graminearum ZJ80 harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.19 ug.mL-1
Fungicidal activity against Fusarium graminearum E198K harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 4.46 ug.mL-1
Fungicidal activity against Fusarium graminearum F200Y harboring mutation at codon 200 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 6.05 ug.mL-1
Fungicidal activity against Fusarium graminearum J2 harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 5.81 ug.mL-1
Fungicidal activity against Fusarium graminearum NT7 harboring mutation at codon 200 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 8.83 ug.mL-1
Fungicidal activity against Fusarium graminearum F167Y harboring mutation at codon 167 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 14.99 ug.mL-1
Fungicidal activity against Fusarium graminearum 2052 harboring mutation at codon 167 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 17.68 ug.mL-1
Fungicidal activity against Fusarium graminearum Y50C harboring mutation at codon 50 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.02 ug.mL-1
Fungicidal activity against Fusarium graminearum 2021 assessed as mycelial growth inhibition after 3 days Fusarium graminearum 0.61 ug.mL-1
Fungicidal activity against Fusarium graminearum DN83 harboring beta2 tubulin deletion mutation assessed as mycelial growth inhibition after 3 days Fusarium graminearum None
Growth inhibition of Phomopsis obscurans at 100 uM after 48 hr by microtiter assay Phomopsis obscurans 100.0 %
Growth inhibition of Colletotrichum fragariae at 300 uM after 48 hr by microtiter assay Colletotrichum fragariae 76.0 %
Growth inhibition of Fusarium oxysporum at 300 uM after 48 hr by microtiter assay Fusarium oxysporum 77.0 %
Growth inhibition of Colletotrichum acutatum at 300 uM after 48 hr by microtiter assay Colletotrichum acutatum 33.0 %
Antifungal activity against Penicillium brevicompactum Dierckx ITEM-449 after 72 hr by broth dilution method Penicillium brevicompactum 25.0 ug.mL-1
Antifungal activity against Penicillium brevicompactum Dierckx ITEM-449 after 48 hr by broth dilution method Penicillium brevicompactum 25.0 ug.mL-1
Antifungal activity against Penicillium brevicompactum Dierckx ITEM-449 after 24 hr by broth dilution method Penicillium brevicompactum 25.0 ug.mL-1
Antifungal activity against Aspergillus parasiticus Speare ITEM-11 after 72 hr by broth dilution method Aspergillus parasiticus 25.0 ug.mL-1
Antifungal activity against Aspergillus parasiticus Speare ITEM-11 after 48 hr by broth dilution method Aspergillus parasiticus 25.0 ug.mL-1
Antifungal activity against Aspergillus parasiticus Speare ITEM-11 after 24 hr by broth dilution method Aspergillus parasiticus 25.0 ug.mL-1
Antifungal activity against Botryotinia fuckeliana ITEM-966 after 72 hr by broth dilution method Botryotinia fuckeliana 0.19 ug.mL-1
Antifungal activity against Botryotinia fuckeliana ITEM-966 after 48 hr by broth dilution method Botryotinia fuckeliana 0.19 ug.mL-1
Antifungal activity against Botryotinia fuckeliana ITEM-966 after 24 hr by broth dilution method Botryotinia fuckeliana 0.19 ug.mL-1
Antifungal activity against Leptosphaeria maculans assessed as ascospore germination at 1 to 4 ug/ml after 22 hr Leptosphaeria maculans 96.0 %
Antifungal activity against Leptosphaeria maculans assessed as viable conidia at 2 to 4 ug/ml after 1 week Leptosphaeria maculans None
Antifungal activity against Leptosphaeria biglobosa assessed as viable conidia at 2 to 4 ug/ml after 1 week Leptosphaeria biglobosa None
Antifungal activity against Leptosphaeria maculans assessed as reduction of conidia production at 1 to 4 ug/ml after 2 weeks Leptosphaeria maculans None
Antifungal activity against Leptosphaeria biglobosa assessed as reduction of conidia production at 1 to 4 ug/ml after 2 weeks Leptosphaeria biglobosa None
Antifungal activity against Leptosphaeria biglobosa assessed as viable ascospore at 1 to 4 ug/ml after 1 week Leptosphaeria biglobosa None
Antifungal activity against Leptosphaeria maculans assessed as viable ascospore at 1 to 4 ug/ml after 1 week Leptosphaeria maculans None
Antifungal activity against Leptosphaeria biglobosa assessed as reduction of germ tube length at 4 ug/ml after 22 hr relative to control Leptosphaeria biglobosa 81.6 %
Antifungal activity against Leptosphaeria biglobosa assessed as reduction of germ tube length at 2 ug/ml after 22 hr relative to control Leptosphaeria biglobosa 85.5 %
Antifungal activity against Leptosphaeria biglobosa assessed as reduction of germ tube length at 1 ug/ml after 22 hr relative to control Leptosphaeria biglobosa 4.5 %
Antifungal activity against Leptosphaeria maculans assessed as reduction of germ tube length at 4 ug/ml after 22 hr relative to control Leptosphaeria maculans 65.8 %
Antifungal activity against Leptosphaeria maculans assessed as reduction of germ tube length at 2 ug/ml after 22 hr relative to control Leptosphaeria maculans 68.3 %
Antifungal activity against Leptosphaeria maculans assessed as reduction of germ tube length at 1 ug/ml after 22 hr relative to control Leptosphaeria maculans 46.8 %
Antifungal activity against Leptosphaeria biglobosa assessed as inhibition of conidia germination at 4 ug/ml after 22 hr Leptosphaeria biglobosa 15.0 %
Antifungal activity against Leptosphaeria maculans assessed as inhibition of conidia germination at 4 ug/ml after 22 hr Leptosphaeria maculans 80.0 %
Antifungal activity against Leptosphaeria biglobosa assessed as ascospore germination at 1 to 4 ug/ml after 22 hr Leptosphaeria biglobosa 94.0 %

Cross References

Resources Reference
ChEMBL CHEMBL327919
FDA SRS TLW21058F5
PubChem 28780
SureChEMBL SCHEMBL15681
ZINC ZINC01532046