CLOTHIANIDINE

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UNII 2V9906ABKQ
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 PGOOBECODWQEAB-UHFFFAOYSA-N
Smiles CN\C(=N/[N+](=O)[O-])\NCc1cnc(Cl)s1
InChI
InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H8ClN5O2S
Molecular Weight 249.68
AlogP 2.63
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 123.36
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 15.0
Assay Description Organism Bioactivity Reference
Inhibition of Oryctolagus cuniculus (rabbit) AOX in liver cytosol at IC50 concentration Oryctolagus cuniculus 4.0 %
Inhibition of Agaricus bisporus (mushroom) tyrosinase at IC50 concentration Agaricus bisporus 15.0 %
Inhibition of xanthine oxidase None 1860000.0 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 Spinacia oleracea (spinach) seedlings assessed as lesions at 100 ppm after 9 days Spinacia oleracea None
Phytotoxicity against Glycine max (soybean) seedlings assessed as lesions in unfoliolate leaves at 100 ppm after 9 days Glycine max None
Insecticidal activity against adult Aphis gossypii (cotton aphid) in cucumber cotyledons assessed as mortality at 500 ppm treated for 5 secs before adult infestation measured after 72 hr Aphis gossypii 100.0 %
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Drosophila melanogaster brain Drosophila melanogaster 4.0 nM
Competitive inhibition of nicotinic acetylcholine receptor in Drosophila melanogaster head membrane using [3H]IMI as substrate incubated for 5 min prior to substrate addition measured after 90 min by Sctachard plot analysis Drosophila melanogaster None
Competitive inhibition of nicotinic acetylcholine receptor in Myzus persicae (green peach aphid) whole body membrane using [3H]IMI as substrate incubated for 5 min prior to substrate addition measured after 90 min by Sctachard plot analysis Myzus persicae None
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Drosophila melanogaster head membrane after 90 min by filter binding assay Drosophila melanogaster 2.2 nM
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Musca domestica (house fly) head membrane after 90 min by filter binding assay Musca domestica 1.8 nM
Displacement of [3H]IMI from nicotinic acetylcholine receptor in Aphis craccivora (cowpea aphid) whole body membrane after 90 min by filter binding assay Aphis craccivora 2.3 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 9.2 nM
Ratio of EC50 for Daphnia magna to EC50 for first instar larvae of Cheumatopsyche brevilineata None 4.43
Insecticidal activity against first-instar larvae of Cheumatopsyche brevilineata after 48 hr Cheumatopsyche 0.00444 ug.mL-1
Octanol-water partition coefficient, log KOW of the compound None 0.7
Insecticidal activity against Daphnia magna after 48 hr Daphnia magna 119.0 ug.mL-1
Inhibition of Contarinia nasturtii larval development in Brassica oleracea L. var italica plant developed from compound pretreated seeds at 4.5 g AI per 100 g seed measured at 4-5 weeks after planting Contarinia nasturtii 100.0 %
Inhibition of emergence of new-generation Ceutorhynchus obstrictus adults from soil harboring Brassica napus L. Ryder plant developed from compound treated seeds at 600 g/L FS measured for 5 weeks relative to lindane Ceutorhynchus obstrictus 52.2 %
Inhibition of Ceutorhynchus obstrictus preimaginal development in Brassica napus L. Ryder pods of plant developed from compound treated seeds assessed as decrease in number of exit holes formed per pod by third-instar larvae at 600 g/L FS Ceutorhynchus obstrictus None
Inhibition of Ceutorhynchus obstrictus preimaginal development in Brassica napus L. Ryder pods of plant developed from compound treated seeds assessed as decrease in number of third-instar larvae at 600 g/L FS by microscopic analysis Ceutorhynchus obstrictus None
Inhibition of Ceutorhynchus obstrictus preimaginal development in Brassica napus L. Ryder pods of plant developed from compound treated seeds assessed as decrease in number of second-instar larvae at 600 g/L FS by microscopic analysis Ceutorhynchus obstrictus None
Inhibition of Ceutorhynchus obstrictus preimaginal development in Brassica napus L. Ryder pods of plant developed from compound treated seeds assessed as effect on number of first-instar larvae at 600 g/L FS by microscopic analysis Ceutorhynchus obstrictus None
Effect on Ceutorhynchus obstrictus oviposition in Brassica napus L. Ryder pods of plant developed from compound treated seeds assessed as number of eggs deposited at 600 g/L FS by microscopic analysis Ceutorhynchus obstrictus None
Insecticidal activity against Paralobesia viteana infested grapevine assessed as reduction in clusters infested with moth by early-season irrigation injection method (Rvb = 34.3 +/- 4.4 %) Paralobesia 31.7 %
Insecticidal activity against Paralobesia viteana infested grapevine assessed as reduction in clusters infested with moth by mid-season irrigation injection method (Rvb = 11 +/- 1.9 %) Paralobesia 6.0 %
Insecticidal activity against Popillia japonica assessed as reduction in leaf damage measured up to 63 days post treatment by laboratory bioassay Popillia japonica None
Insecticidal activity against Popillia japonica at 500 g/kg WG assessed as reduction in leaf damage measured after 35 days by irrigation injection method (Rvb = 50.97 +/- 7.2 %) Popillia japonica 48.3 %
Insecticidal activity against first generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 106 days after treatment Blissus occiduus None
Insecticidal activity against first generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 8 days after treatment Blissus occiduus None
Insecticidal activity against first generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 3 days after treatment Blissus occiduus None
Resistance index, ratio of LC50 for neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) to LC50 for Myzus persicae 4106A Myzus persicae 3013.0
Insecticidal activity against Myzus persicae 4106A (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr Myzus persicae 0.3 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 904.0 ppm
Displacement of [3H]IMD from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 2.7 nM
Displacement of [3H]-methyl-SFX from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min Myzus persicae 0.058 nM
Insecticidal activity against Popillia japonica at 500 g/kg WG assessed as moribund behaviour measured after 10 to 19 days by irrigation injection method Popillia japonica None
Insecticidal activity against Popillia japonica at 500 g/kg WG assessed as moribund behaviour measured after 3 days by irrigation injection method Popillia japonica None
Insecticidal activity against Popillia japonica at 500 g/kg WG assessed as moribund behaviour measured after 24 to 56 days by irrigation injection method Popillia japonica None
Insecticidal activity against Popillia japonica assessed as mortality after 30 days Popillia japonica 32.8 %
Insecticidal activity against Popillia japonica assessed as mortality after 20 days Popillia japonica 22.9 %
Insecticidal activity against Popillia japonica assessed as mortality after 10 days Popillia japonica 4.0 %
Insecticidal activity against Maladera castanea assessed as mortality after 20 days Maladera castanea 75.7 %
Insecticidal activity against Maladera castanea assessed as mortality after 30 days Maladera castanea 100.0 %
Insecticidal activity against Maladera castanea assessed as mortality after 10 days Maladera castanea 39.8 %
Insecticidal activity against Anomala orientalis assessed as mortality after 30 days Anomala orientalis 98.6 %
Insecticidal activity against Anomala orientalis assessed as mortality after 20 days Anomala orientalis 89.3 %
Insecticidal activity against Anomala orientalis assessed as mortality after 10 days Anomala orientalis 56.0 %
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 30 days Amphimallon majalis 44.3 %
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 20 days Amphimallon majalis 22.6 %
Insecticidal activity against Amphimallon majalis (European chafer) assessed as mortality after 10 days Amphimallon majalis 19.8 %
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 6.61 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 72.7 %
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 0.12 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 0.14 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 1.23 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 0.16 mg
Resistance ratio, LC50 for Aphis gossypii RF45 (cotton aphid) to LC50 for Aphis gossypii SS Aphis gossypii 1.2
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 2.18 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 1.82 microg/mL2
Hydrophobicity, log K of the compound by HPLC None 0.17
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing measured per insect at 25 to 28 degC for 24 hr in presence of piperonyl butoxide Periplaneta americana 10.2
Agonist activity at Periplaneta americana (American cockroach) nAChR in terminal abdominal ganglion assessed as assessed as inward current by tight-seal whole cell patch clamp method relative to 100 uM ACh Periplaneta americana 0.68
Agonist activity at Periplaneta americana (American cockroach) nAChR in terminal abdominal ganglion assessed as assessed as inward current by tight-seal whole cell patch clamp method Periplaneta americana 1584.89 nM
Drug level in Urochloa mutica (buffalo grass) measured per gram of fresh weight at 19.1 kg/ha measured 28 days after treatment Urochloa mutica 0.19 ug
Drug level in Urochloa mutica (buffalo grass) measured per gram of fresh weight at 19.1 kg/ha measured 14 days after treatment Urochloa mutica 0.66 ug
Drug level in Urochloa mutica (buffalo grass) measured per gram of fresh weight at 19.1 kg/ha measured 7 days after treatment Urochloa mutica 1.56 ug
Drug level in Urochloa mutica (buffalo grass) measured per gram of fresh weight at 19.1 kg/ha measured 3 days after treatment Urochloa mutica 6.48 ug
Insecticidal activity against second generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 55 days after treatment Blissus occiduus None
Insecticidal activity against second generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 28 days after treatment Blissus occiduus None
Insecticidal activity against second generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 7 days after treatment Blissus occiduus None
Insecticidal activity against second generation Blissus occiduus in buffalograss under field condition assessed as reduction in number at 89.7 kg/ha measured 3 days after treatment Blissus occiduus None

Cross References

Resources Reference
ChEMBL CHEMBL259727
FDA SRS 2V9906ABKQ
PDB CT4
SureChEMBL SCHEMBL21214
ZINC ZINC13827936
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