METHOXYFENOZIDE

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Synonyms
UNII 62A22651ZX
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 QCAWEPFNJXQPAN-UHFFFAOYSA-N
Smiles COc1cccc(C(=O)NN(C(=O)c2cc(C)cc(C)c2)C(C)(C)C)c1C
InChI
InChI=1S/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25)

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H28N2O3
Molecular Weight 368.47
AlogP 4.45
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 58.64
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0
Assay Description Organism Bioactivity Reference
Stomach toxicity against third-instar Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as insecticidal activity at 200 mg/L measured after 4 days by leaf-dip method Mythimna separata 100.0 %
Stomach toxicity against third-instar Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as insecticidal activity at 100 mg/L measured after 4 days by leaf-dip method Mythimna separata 100.0 %
Stomach toxicity against third-instar Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as insecticidal activity at 50 mg/L measured after 4 days by leaf-dip method Mythimna separata 100.0 %
Stomach toxicity against third-instar Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as insecticidal activity at 25 mg/L measured after 4 days by leaf-dip method Mythimna separata 100.0 %
Stomach toxicity against third-instar Mythimna separata (Oriental armyworm) in compound treated fresh corn leaves assessed as insecticidal activity at 10 mg/L measured after 4 days by leaf-dip method Mythimna separata 100.0 %
Stomach toxicity against third-instar Spodoptera exigua in compound treated fresh cabbage leaves assessed as insecticidal activity at 200 mg/L measured after 3 days by leaf-dip method Spodoptera exigua 100.0 %
Stomach toxicity against third-instar Spodoptera exigua in compound treated fresh cabbage leaves assessed as insecticidal activity at 100 mg/L measured after 3 days by leaf-dip method Spodoptera exigua 100.0 %
Stomach toxicity against third-instar Spodoptera exigua in compound treated fresh cabbage leaves assessed as insecticidal activity at 50 mg/L measured after 3 days by leaf-dip method Spodoptera exigua 100.0 %
Stomach toxicity against third-instar Spodoptera exigua in compound treated fresh cabbage leaves assessed as insecticidal activity at 10 mg/L measured after 3 days by leaf-dip method Spodoptera exigua 100.0 %
Stomach toxicity against third-instar Plutella xylostella (diamondback moth) in compound treated fresh cabbage leaves assessed as insecticidal activity at 200 mg/L measured after 3 days by leaf-dip method Plutella xylostella 100.0 %
Stomach toxicity against third-instar Plutella xylostella (diamondback moth) in compound treated fresh cabbage leaves assessed as insecticidal activity at 100 mg/L measured after 3 days by leaf-dip method Plutella xylostella 100.0 %
Stomach toxicity against third-instar Plutella xylostella (diamondback moth) in compound treated fresh cabbage leaves assessed as insecticidal activity at 50 mg/L measured after 3 days by leaf-dip method Plutella xylostella 100.0 %
Stomach toxicity against third-instar Ostrinia nubilalis (European corn borer) in compound treated fresh corn leaves assessed as insecticidal activity at 200 mg/L measured after 4 days by leaf-dip method Ostrinia nubilalis 100.0 %
Stomach toxicity against Mythimna separata (Oriental armyworm) fourth-instar larvae reared on compound pre-treated corn leaves assessed as insect mortality at 2.5 mg/kg measured 4 days post compound treatment Mythimna separata 100.0 %
Stomach toxicity against Mythimna separata (Oriental armyworm) fourth-instar larvae reared on compound pre-treated corn leaves assessed as insect mortality at 5 mg/kg measured 4 days post compound treatment Mythimna separata 100.0 %
Dissociation constant, pKa of the compound at pH 7.3 None 0.0
Apparent hydrophobicity, log D of the compound in Octanol-buffer None 3.7
Apparent permeability of the compound by PAMPA None -4.72
Hydrophobicity, log P of the compound in octanol-water by shaking-flask method None 3.7
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr (Rvb = 16.1%) Metaseiulus occidentalis 9.0 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 48 hr (Rvb = 13.6%) Metaseiulus occidentalis 5.8 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 24 hr (Rvb = 3.6%) Metaseiulus occidentalis 3.8 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as average number of eggs laid (fecundity) at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr (Rvb = 2.23/day) Metaseiulus occidentalis 2.38 /day
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as average number of eggs laid (fecundity) at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 48 hr (Rvb = 2.30/day) Metaseiulus occidentalis 2.15 /day
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as average number of eggs laid (fecundity) at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 24 hr (Rvb = 2.11/day) Metaseiulus occidentalis 1.93 /day
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as corrected mortality at 0.3767 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr Metaseiulus occidentalis 1.3 %
Ovicidal activity against Metaseiulus occidentalis eggs in bean leaf disk infested with two-spotted spider mites assessed as corrected cumulative mortality at 240 g/L SC formulation treated using worst-case laboratory exposure procedure measured after 144 hr (Rvb = 0.7%) Metaseiulus occidentalis 3.1 %
Ratio of LD50 for Spodoptera littoralis to LD50 for Bombyx mori None 3.16
Larvicidal activity against Spodoptera littoralis assessed as mortality applied topically after 1 week Spodoptera littoralis 7.68
Larvicidal activity against Bombyx mori assessed as mortality applied topically after 1 week Bombyx mori 8.18
Selectivity ratio of EC50 for ecdysone receptor in Bombyx mori Bm5 cells to EC50 for ecdysone receptor in Spodoptera littoralis Sl2 cells None 0.56
Agonist activity at ecdysone receptor in Spodoptera littoralis Sl2 cells after 24 hr by luciferase reporter gene assay relative to tebufenozide Spodoptera littoralis 100.0 %
Agonist activity at ecdysone receptor in Spodoptera littoralis Sl2 cells after 24 hr by luciferase reporter gene assay Spodoptera littoralis 6.03 nM
Agonist activity at ecdysone receptor in Bombyx mori Bm5 cells after 24 hr by luciferase reporter gene assay relative to tebufenozide Bombyx mori 103.0 %
Agonist activity at ecdysone receptor in Bombyx mori Bm5 cells after 24 hr by luciferase reporter gene assay Bombyx mori 3.39 nM
Insecticidal activity against po dosed 20 day-old larvae of Cydia pomonella (codling moth) reared on apple assessed as mortality measured after 4 days Cydia pomonella 50.0 %
Insecticidal activity against po dosed 15 day-old larvae of Cydia pomonella (codling moth) reared on apple assessed as mortality measured after 4 days Cydia pomonella 55.1 %
Insecticidal activity against po dosed 10 day-old larvae of Cydia pomonella (codling moth) Owensby reared on apple assessed as mortality measured after 4 days Cydia pomonella 31.3 %
Insecticidal activity against po dosed 10 day-old larvae of Cydia pomonella (codling moth) Gilbert reared on apple assessed as mortality measured after 4 days Cydia pomonella 93.6 %
Insecticidal activity against po dosed 11 day-old larvae of spinetoram-selected Cydia pomonella (codling moth) reared on apple assessed as mortality measured after 4 days Cydia pomonella 83.3 %
Insecticidal activity against po dosed 10 day-old larvae of Chlorantraniliprole-selected Cydia pomonella (codling moth) reared on apple assessed as mortality measured after 4 days Cydia pomonella 100.0 %
Insecticidal activity against po dosed 15 day-old larvae of Cydia pomonella (codling moth) lab-s reared on apple assessed as mortality measured after 4 days Cydia pomonella 98.4 %
Insecticidal activity against po dosed 10 day-old larvae of Cydia pomonella (codling moth) lab-s reared on apple assessed as mortality measured after 4 days Cydia pomonella 99.2 %
Insecticidal activity against po dosed 10 day-old larvae of Cydia pomonella (codling moth) lab-s measured after 4 days Cydia pomonella 10.0 ug ml-1
Resistant ratio of LC50 for fourth-instar larvae of Cydia pomonella (codling moth) Holt to fourth-instar larvae of Cydia pomonella (codling moth) Glibert Cydia pomonella 16.7
Resistant ratio of LC50 for Cydia pomonella (codling moth) Holt neonate to Cydia pomonella (codling moth) Glibert neonate Cydia pomonella 24.0
Resistant ratio of LC50 for fourth-instar larvae of Cydia pomonella (codling moth) lab-s to fourth-instar larvae of Cydia pomonella (codling moth) Glibert Cydia pomonella 6.6
Resistant ratio of LC50 for Cydia pomonella (codling moth) lab-s neonate to Cydia pomonella (codling moth) Glibert neonate Cydia pomonella 8.0
Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Gilbert measured after 4 days Cydia pomonella 202.0 ug ml-1 Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Gilbert measured after 4 days Cydia pomonella 15.2 ug.mL-1
Insecticidal activity against po dosed Cydia pomonella (codling moth) Gilbert neonate measured after 4 days Cydia pomonella 389.4 ug ml-1 Insecticidal activity against po dosed Cydia pomonella (codling moth) Gilbert neonate measured after 4 days Cydia pomonella 9.5 ug.mL-1
Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Holt measured after 4 days Cydia pomonella 5061.9 ug ml-1 Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Holt measured after 4 days Cydia pomonella 38.7 ug.mL-1
Insecticidal activity against po dosed Cydia pomonella (codling moth) Holt neonate measured after 4 days Cydia pomonella 5320.8 ug ml-1 Insecticidal activity against po dosed Cydia pomonella (codling moth) Holt neonate measured after 4 days Cydia pomonella 28.5 ug.mL-1
Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Clear Creek abandoned measured after 4 days Cydia pomonella 28.38 ug ml-1 Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) Clear Creek abandoned measured after 4 days Cydia pomonella 1.35 ug.mL-1
Insecticidal activity against po dosed Cydia pomonella (codling moth) Clear Creek abandoned neonate measured after 4 days Cydia pomonella 14.57 ug ml-1 Insecticidal activity against po dosed Cydia pomonella (codling moth) Clear Creek abandoned neonate measured after 4 days Cydia pomonella 95.0 ug.mL-1
Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) lab-s measured after 4 days Cydia pomonella 18.27 ug ml-1 Insecticidal activity against po dosed fourth-instar larvae of Cydia pomonella (codling moth) lab-s measured after 4 days Cydia pomonella 2.3 ug.mL-1
Insecticidal activity against po dosed Cydia pomonella (codling moth) lab-s neonate measured after 4 days Cydia pomonella 14.15 ug ml-1 Insecticidal activity against po dosed Cydia pomonella (codling moth) lab-s neonate measured after 4 days Cydia pomonella 1.2 ug.mL-1
Agonist activity at ecdysone receptor in Drosophila melanogaster S2 cells after 24 hr by luciferase reporter gene assay in presence of ouabain Drosophila melanogaster None
Agonist activity at ecdysone receptor in Drosophila melanogaster S2 cells treated with ouabain for 24 hr prior to compound addition measured after 24 hr by luciferase reporter gene assay Drosophila melanogaster None
Cytotoxicity against Drosophila melanogaster S2 cells at 10 to 100 uM after 24 hr by CellTiter assay Drosophila melanogaster None
Ratio of EC50 for EcR in Drosophila melanogaster S2 cells to EC50 for EcR in Bombyx mori Bm5 cells None 100.0
Agonist activity at ecdysone receptor in Bombyx mori Bm5 cells after 24 hr by luciferase reporter gene assay Bombyx mori 6.03 nM
Agonist activity at ecdysone receptor in Drosophila melanogaster S2 cells at 100 uM after 24 hr by luciferase reporter gene assay relative to 20-hydroxyecdysone Drosophila melanogaster 66.0 %
Agonist activity at ecdysone receptor in Drosophila melanogaster S2 cells after 24 hr by luciferase reporter gene assay Drosophila melanogaster 16595.87 nM
Insecticidal activity against Helicoverpa armigera adults emerged from compound-treated third-instar larval stage assessed as decrease in longevity rate at LC30 concentration Helicoverpa armigera 27.5 %
Insecticidal activity against Helicoverpa armigera adults emerged from compound-treated third-instar larval stage assessed as decrease in fecundity rate at LC30 concentration Helicoverpa armigera 35.0 %
Insecticidal activity against Helicoverpa armigera pupae assessed as increase in pupal development time at LC30 concentration treated during third-instar larval stage for 24 hr Helicoverpa armigera 2.3 day
Insecticidal activity against Helicoverpa armigera assessed as pupal weight at LC30 concentration treated during third-instar larval stage for 24 hr (Rvb = 311 +/-9 mg) Helicoverpa armigera 253.0 mg
Insecticidal activity against third-instar larval stage of Helicoverpa armigera fed with artificial diet containing compound assessed as increase in larval development time at LC30 concentration incubated for 24 hr Helicoverpa armigera 2.1 day
Insecticidal activity against Helicoverpa armigera fed with artificial diet containing compound assessed as mortality at LC30 concentration measured at 24 hr intervals beginning at 24 hr after initial drug exposure Helicoverpa armigera 32.0 %
Insecticidal activity against third-instar larval stage of Helicoverpa armigera fed with artificial diet containing compound assessed as mortality at LC30 concentration measured at 24 hr intervals beginning at 24 hr after initial drug exposure Helicoverpa armigera 32.0 %
Insecticidal activity against third-instar larval stage of Helicoverpa armigera fed with artificial diet containing compound assessed as mortality measured at 24 hr intervals beginning at 24 hr after initial drug exposure Helicoverpa armigera 560.0 ppm Insecticidal activity against third-instar larval stage of Helicoverpa armigera fed with artificial diet containing compound assessed as mortality measured at 24 hr intervals beginning at 24 hr after initial drug exposure Helicoverpa armigera 218.0 ppm Insecticidal activity against third-instar larval stage of Helicoverpa armigera fed with artificial diet containing compound assessed as mortality measured at 24 hr intervals beginning at 24 hr after initial drug exposure Helicoverpa armigera 148.0 ppm
Antifeedant activity against third-instar larval stage of Plutella xylostella (diamondback moth) infested compound-treated leaf assessed as reduction in feeding damage at 467 mg a.i/L after 48 hr by leaf disk assay relative to untreated control Plutella xylostella 96.0 %
Antifeedant activity against third-instar larval stage of Plutella xylostella (diamondback moth) infested compound-treated leaf assessed as time required to stop feeding at 467 mg a.i/L after 48 hr by leaf disk assay (Rvb = > 2880 min) Plutella xylostella 514.5 min
Antifeedant activity against third-instar larval stage of Trichoplusia ni (cabbage looper) infested compound-treated leaf assessed as reduction in feeding damage at 467 mg a.i/L after 48 hr by leaf disk assay relative to untreated control Trichoplusia ni 81.6 %
Antifeedant activity against third-instar larval stage of Trichoplusia ni (cabbage looper) infested compound-treated leaf assessed as time required to stop feeding at 467 mg a.i/L after 48 hr by leaf disk assay (Rvb = > 2880 min) Trichoplusia ni 408.8 min
Antifeedant activity against third-instar larval stage of Spodoptera exigua infested compound-treated leaf assessed as time required to stop feeding at 467 mg a.i/L after 48 hr by leaf disk assay (Rvb = > 2880 min) Spodoptera exigua 281.1 min
Antifeedant activity against third-instar larval stage of Spodoptera exigua infested compound-treated leaf assessed as reduction in feeding damage at 467 mg a.i/L after 48 hr by leaf disk assay relative to untreated control Spodoptera exigua 72.9 %
Antifeedant activity against third-instar larval stage of Helicoverpa zea (corn earworm) infested compound-treated leaf assessed as time required to stop feeding at 467 mg a.i/L after 48 hr by leaf disk assay (Rvb = > 2880 min) Helicoverpa zea 471.8 min
Antifeedant activity against third-instar larval stage of Helicoverpa zea (corn earworm) infested compound-treated leaf assessed as reduction in feeding damage at 467 mg a.i/L after 48 hr by leaf disk assay relative to untreated control Helicoverpa zea 93.3 %
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through residual contact on glass surfaces measured after 15 days (Rvb = 45.8 +/- 16.3%) Bactrocera oleae 49.1 %
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through residual contact on glass surfaces measured after 7 days (Rvb = 4.0 +/- 4.0%) Bactrocera oleae 0.0 %
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through residual contact on glass surfaces measured after 24 hr (Rvb = 2.0 +/- 2.0%) Bactrocera oleae 0.0 %
Insecticidal activity against Bactrocera oleae assessed as insect survival lifespan at 96 mg Ai/L applied through oral ingestion (Rvb = 79.7 +/- 12.2 days) Bactrocera oleae 8.6 day
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through oral ingestion measured after 15 days (Rvb = 2.5 +/- 2.5%) Bactrocera oleae 2.5 %
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through oral ingestion measured after 7 days (Rvb = 2.5 +/- 2.5%) Bactrocera oleae 2.5 %
Insecticidal activity against Bactrocera oleae assessed as insect mortality at 96 mg Ai/L applied through oral ingestion measured after 24 hr (Rvb = 0%) Bactrocera oleae 2.5 %
Resistance ratio, ratio of LC50 for third-instar larvae of fufenozide-resistant Plutella xylostella (diamondback moth) to LC50 for third-instar larvae of fufenozide-susceptible Plutella xylostella Plutella xylostella 37.6
Insecticidal activity against third-instar larvae of fufenozide-susceptible Plutella xylostella (diamondback moth) assessed as mortality by leaf-dip bioassay method Plutella xylostella 7.33 ug.mL-1
Insecticidal activity against third-instar larvae of fufenozide-resistant Plutella xylostella (diamondback moth) assessed as mortality by leaf-dip bioassay method Plutella xylostella 275.8 ug.mL-1

Cross References

Resources Reference
ChEMBL CHEMBL55772
FDA SRS 62A22651ZX
PubChem 105010
SureChEMBL SCHEMBL27595
ZINC ZINC02511852
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