Synonyms
UNII DSV3A944A4
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 HOKKPVIRMVDYPB-UVTDQMKNSA-N
Smiles Clc1ccc(CN2CCS/C/2=N\C#N)cn1
InChI
InChI=1S/C10H9ClN4S/c11-9-2-1-8(5-13-9)6-15-3-4-16-10(15)14-7-12/h1-2,5H,3-4,6H2/b14-10-

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H9ClN4S
Molecular Weight 252.72
AlogP 2.1
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 77.58
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 16.0
Assay Description Organism Bioactivity Reference
Inhibition of Oryctolagus cuniculus (rabbit) AOX in liver cytosol at IC50 concentration Oryctolagus cuniculus 8.0 %
Inhibition of xanthine oxidase at IC50 concentration None 3.0 %
Inhibition of Agaricus bisporus (mushroom) tyrosinase at IC50 concentration Agaricus bisporus 22.0 %
Inhibition of xanthine oxidase None 1000000.0 nM
Inhibition of Oryctolagus cuniculus (rabbit) AOX in liver cytosol Oryctolagus cuniculus 1000000.0 nM
Inhibition of Agaricus bisporus (mushroom) tyrosinase Agaricus bisporus 1000000.0 nM
Phytotoxicity against Vitis vinifera seedlings assessed as lesions at 50 to 100 ppm after 9 days Vitis vinifera None
Phytotoxicity against Zea mays (maize) seedlings assessed as lesions at 50 to 100 ppm after 9 days Zea mays None
Phytotoxicity against Gossypium hirsutum (cotton) seedlings assessed as lesions at 50 to 100 ppm after 9 days Gossypium hirsutum None
Phytotoxicity against Glycine max (soybean) seedlings assessed as lesions in unfoliolate leaves at 100 ppm after 9 days Glycine max None
Displacement of fluorescent probe 1-NPN from Acyrthosiphon pisum (pea aphid) recombinant OBP3 by competitive binding assay Acyrthosiphon pisum None
Risk quotient, recommended field rate (g/ha) to LC50 for Trichogramma nubilale (mg/L) Trichogramma nubilale 1.78
Contact toxicity against Trichogramma nubilale assessed as mortality after 24 hr by modified slight dry film method Trichogramma nubilale 461.2 mgAi/L Contact toxicity against Trichogramma nubilale assessed as mortality after 24 hr by modified slight dry film method Trichogramma nubilale 56.73 mgAi/L
Binding affinity to freshwater snail Lymnaea stagnalis AChBP assessed as [3H]EPI binding by radioligand binding assay Lymnaea stagnalis 220.0 nM
Binding affinity to salt water mollusc Aplysia californica AChBP Y55W mutant assessed as [3H]acetamiprid binding by radioligand binding assay Aplysia californica 3.9 nM
Binding affinity to recombinant Gallus gallus (chicken) alpha4beta2 nicotinic acetylcholine receptor assessed as [3H]NIC binding by radioligand binding assay Gallus gallus 240.0 nM
Binding affinity to Drosophila brain nicotinic acetylcholine receptor assessed as [3H]IMI binding by radioligand binding assay Drosophila 1.2 nM
Retention time under basic conditions using 20 mM Na2HPO4 (pH9.9)/MeOH (1:1) mobile phase by HPLC method None 6.05 min
Retention time under acidic conditions using H20/MeOH mobile phase containing 0.1% TFA (1:1) by HPLC method None 6.07 min
Retention time under neutral conditions using H20/MeOH (1:1) mobile phase by HPLC method None 6.06 min
Inhibition of [3H]nicotine binding to alpha4 nicotinic acetylcholine receptor in Mus musculus (mouse) M10 cells co-expressing beta2 nicotinic acetylcholine receptor subunits Mus musculus 860.0 nM
Inhibition of [3H]nicotine binding to alpha3 nicotinic acetylcholine receptor in Homo sapiens (human) SH-SY5Y cells co-expressing beta2beta4alpha5 Nicotinic acetylcholine receptor subunits Homo sapiens None
Inhibition of [3H]alpha-BGT binding to alpha7 nicotinic acetylcholine receptor in Homo sapiens (human) SH-SY5Y cells Homo sapiens 100000.0 nM
Inhibition of [3H]alpha-BGT binding to alpha1 nicotinic acetylcholine receptor in Homo sapiens (human) TE671 cells co-expressing gammaalpha1deltabeta1 nicotinic acetylcholine receptor subunits Homo sapiens 120000.0 nM
Toxicity against Musca domestica (house fly) dosed with compound through intra-thoracic injection pre-treated with 100 ug/g metabolic detoxification inhibitor O-propyl O-(2-propynyl)phenylphosphonate Musca domestica 0.03 mg.kg-1
Toxicity in ip dosed Mus musculus (mouse) Mus musculus 25.0 mg.kg-1
Inhibition of [3H]IMI binding to Drosophila melanogaster neuronal acetylcholine receptor Drosophila melanogaster 2.7 nM
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Drosophila melanogaster head membrane after 90 min by filter binding assay Drosophila melanogaster 7.5 nM
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Myzus persicae (green peach aphid) whole body membrane after 90 min by filter binding assay Myzus persicae 3.4 nM
Ratio of EC50 for Daphnia magna to EC50 for first instar larvae of Cheumatopsyche brevilineata None 3.63
Insecticidal activity against first-instar larvae of Cheumatopsyche brevilineata after 48 hr Cheumatopsyche 0.00527 ug.mL-1
Octanol-water partition coefficient, log KOW of the compound None 1.26
Insecticidal activity against Daphnia magna after 48 hr Daphnia magna 22.52 ug.mL-1
Resistance factor, ratio of LC50 for adult female Bemisia tabaci B-biotype NJ-Imi (sweet potato whitefly) (G30) to LC50 for adult female B-type Bemisia tabaci NJ Bemisia tabaci 37.0
Insecticidal activity against adult female imidacloprid-resistant Bemisia tabaci B-biotype NJ-Imi (sweet potato whitefly) (G30) in cotton leaf discs assessed as mortality treated for 10 secs prior to adult infestation measured after 72 hr by leaf-dip bioassay Bemisia tabaci 37.3 ug.mL-1
Insecticidal activity against adult female imidacloprid-susceptible Bemisia tabaci B-biotype NJ (sweet potato whitefly) in cotton leaf discs assessed as mortality treated for 10 secs prior to adult infestation measured after 72 hr by leaf-dip bioassay Bemisia tabaci 1.02 ug.mL-1
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr (Rvb = 16.1%) Metaseiulus occidentalis 49.4 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 48 hr (Rvb = 13.6%) Metaseiulus occidentalis 44.9 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as repellency at 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 24 hr (Rvb = 3.6%) Metaseiulus occidentalis 12.2 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as average number of eggs laid (fecundity) at 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr (Rvb = 2.23/day) Metaseiulus occidentalis 1.58 /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 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 48 hr (Rvb = 2.30/day) Metaseiulus occidentalis 1.26 /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 0.1333 g AI/L treated using worst-case laboratory exposure procedure measured after 24 hr (Rvb = 2.11/day) Metaseiulus occidentalis 1.64 /day
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as corrected mortality at 0.1600 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr Metaseiulus occidentalis 2.8 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as corrected mortality at 2x0.1600 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr Metaseiulus occidentalis 2.3 %
Toxicity against Metaseiulus occidentalis adults in bean leaf disk infested with two-spotted spider mites assessed as corrected mortality at 4x0.1600 g AI/L treated using worst-case laboratory exposure procedure measured after 72 hr Metaseiulus occidentalis 5.8 %
Ovicidal activity against Metaseiulus occidentalis eggs in bean leaf disk infested with two-spotted spider mites assessed as corrected cumulative mortality at 480 g/L SC formulation treated using worst-case laboratory exposure procedure measured after 144 hr (Rvb = 0.7%) Metaseiulus occidentalis 1.9 %
Resistance index, ratio of LC50 for neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) to LC50 for Myzus persicae 4106A Myzus persicae 2500.0
Insecticidal activity against Myzus persicae 4106A (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr Myzus persicae 0.4 ppm
Insecticidal activity against neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr Myzus persicae 1000.0 ppm
Displacement of [3H]IMD from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 0.17 nM
Displacement of [3H]-methyl-SFX from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 0.041 nM
Octanol-water partition coefficient, log P of the compound at 23 degC by shake flask method None 1.2
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing compound injected into abdomen of cockroach after 24 hr in presence of 50 ug piperonyl butoxide oxidative metabolism inhibitor and 50 ug propargyl propyl benzenephosphonate inhibitor of hydrolytic Periplaneta americana 0.21 nmol
Insecticidal activity against Periplaneta americana (American cockroach) assessed as neuroblocking concentration Periplaneta americana 2.6 uM
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing compound injected into abdomen of cockroach after 24 hr in presence of 50 ug propargyl propyl benzenephosphonate inhibitor of hydrolytic metabolism of tetramethrin pyrethroid Periplaneta americana 0.46 nmol
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing compound injected into abdomen of cockroach after 24 hr in presence of 50 ug piperonyl butoxide oxidative metabolism inhibitor Periplaneta americana 5.9 nmol
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing compound injected into abdomen of cockroach after 24 hr Periplaneta americana 21.0 nmol
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as fecundity at LC20 concentration Aphis gossypii None
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as longevity at LC20 concentration Aphis gossypii 10.6 day
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as inhibition of honeydew excretion at LC20 concentration measured after 72 hr by dipping method Aphis gossypii 36.9 %
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 72 hr by dipping method (Rvb = 0.40 +/- 0.0002 mg/aphid) Aphis gossypii 0.16 mg
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 48 hr by dipping method (Rvb = 0.36 +/- 0.0006 mg/aphid) Aphis gossypii 0.18 mg
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as mortality measured after 72 hr by dipping method Aphis gossypii 5.45 ug ml-1
Insecticidal activity against imidacloprid-resistant Aphis gossypii (cotton aphid) in cotton leaves assessed as reduction in body weight at LC20 concentration measured after 24 hr by dipping method (Rvb = 0.33 +/- 0.0004 mg/aphid) Aphis gossypii 0.19 mg
Resistance ratio, LC50 for Aphis gossypii RF45 (cotton aphid) to LC50 for Aphis gossypii SS Aphis gossypii 3.68
Insecticidal activity against imidacloprid-resistant Aphis gossypii RF45 (cotton aphid) in cotton leaves assessed as mortality measured after 48 hr by dipping method Aphis gossypii 8.69 microg/mL2
Insecticidal activity against Aphis gossypii SS (cotton aphid) in cotton leaves assessed as mortality measured after 48 hr by dipping method Aphis gossypii 2.36 microg/mL2
Insecticidal activity against Frankliniella occidentalis SPI5 (western flower thrips) in compound treated sweet pepper leaf assessed as mortality at 216 mg/l at 25 +/- 2 degC by leaf dip method Frankliniella occidentalis 3.3 %
Insecticidal activity against Frankliniella occidentalis TFA (western flower thrips) in compound treated sweet pepper leaf assessed as mortality at 216 mg/l at 25 +/- 2 degC by leaf dip method Frankliniella occidentalis 3.3 %
Insecticidal activity against Frankliniella occidentalis R1 (western flower thrips) in compound treated sweet pepper leaf assessed as mortality at 216 mg/l at 25 +/- 2 degC by leaf dip method Frankliniella occidentalis 0.0 %
Insecticidal activity against Frankliniella occidentalis TFB (western flower thrips) in compound treated sweet pepper leaf assessed as mortality at 216 mg/l at 25 +/- 2 degC by leaf dip method Frankliniella occidentalis 10.0 %

Cross References

Resources Reference
ChEMBL CHEMBL451432
FDA SRS DSV3A944A4
PDB TH4
SureChEMBL SCHEMBL26490
ZINC ZINC13828082