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Chlorothalonil

AlkaPlorer ID: AK044474

Synonym: None

IUPAC Name: 2,4,5,6-tetrachlorobenzene-1,3-dicarbonitrile

Structure

SMILES: N#CC1=C(Cl)C(C#N)=C(Cl)C(Cl)=C1Cl

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InChI: InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14

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InChIKey: CRQQGFGUEAVUIL-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 265.914

TPSA？: 47.58

MolLogP？: 4.043559999999999

Number of H-Donors: 0

Number of H-Acceptors: 2

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Alternaria solani Alternaria solani Activity 73.3 % 10.1016/j.ejmech.2021.114057
Aphidius colemani Aphidius colemani Cmin 0.7 ng 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani Cmin 0.9 ng 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani Drug uptake 5.5 ng 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani Drug uptake 25.1 ng 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani mortality 0.0 % 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani mortality 8.7 % 10.1584/jpestics.30.11
Aphidius colemani Aphidius colemani mortality 30.0 % 10.1584/jpestics.30.11
Aspergillus flavus Aspergillus flavus MIC 7.81 ug.mL-1 10.1016/j.bmc.2019.115088
Aspergillus niger Aspergillus niger MIC 15.63 ug.mL-1 10.1016/j.bmc.2019.115088
Aspergillus niger Aspergillus niger MIC 52.0 ug.mL-1 10.1016/j.bmc.2012.04.045
Bacillus cereus Bacillus cereus IZ 15.5 mm 10.1016/j.bmcl.2013.08.068
Bacillus cereus Bacillus cereus IZ 20.2 mm 10.1016/j.bmcl.2013.02.033
Bacillus cereus Bacillus cereus MBC99.9 1.7 ug ml-1 10.1016/j.bmcl.2013.08.068
Bacillus cereus Bacillus cereus MIC 0.7 ug.mL-1 10.1016/j.bmcl.2013.02.033
Bacillus cereus Bacillus cereus MIC 0.7 ug.mL-1 10.1016/j.bmcl.2013.08.068
Bipolaris maydis Bipolaris maydis Activity 91.3 % 10.1016/j.ejmech.2021.114057
Blumeria graminis Blumeria graminis Activity 0.0 % 10.1021/jf0210369
Botryosphaeria berengeriana Botryosphaeria berengeriana Inhibition 92.5 % 10.1016/j.ejmech.2019.02.002
Botrytis cinerea Botrytis cinerea Activity 0.0 % 10.1021/jf0210369
Botrytis cinerea Botrytis cinerea EC50 nan None 10.1021/jf903665f
Botrytis cinerea Botrytis cinerea Inhibition 23.29 % 10.1021/jf9043277
Botrytis cinerea Botrytis cinerea Inhibition 95.0 % 10.3390/molecules16118945
Candida albicans Candida albicans IZ 9.9 mm 10.1016/j.bmcl.2013.02.033
Candida albicans Candida albicans IZ 17.0 mm 10.1016/j.bmcl.2013.08.068
Candida albicans Candida albicans MFC99.9 7.8 ug ml-1 10.1016/j.bmcl.2013.08.068
Candida albicans Candida albicans MIC 0.5 ug.mL-1 10.1016/j.bmcl.2013.02.033
Candida albicans Candida albicans MIC 0.7 ug.mL-1 10.1016/j.bmcl.2013.08.068
Ceratobasidium cereale Ceratobasidium cereale EC50 5.3 ug.mL-1 10.1016/j.ejmech.2019.02.002
Ceratobasidium cereale Ceratobasidium cereale Inhibition 96.8 % 10.1016/j.ejmech.2019.02.002
Colletotrichum Colletotrichum Inhibition 78.6 % 10.1016/j.ejmech.2019.02.002
Colletotrichum fragariae Colletotrichum fragariae IZ 280.0 mm 10.1021/np990628r
Colletotrichum lagenaria Colletotrichum lagenaria IC50 0.87 ug.mL-1 10.1021/jf205123d
Colletotrichum orbiculare Colletotrichum orbiculare Activity nan None 10.1021/jf035204o
Colletotrichum orbiculare Colletotrichum orbiculare Inhibition nan % 10.1021/jf050957r
Colletotrichum orbiculare Colletotrichum orbiculare MIC 250.0 ug.mL-1 10.1016/j.bmc.2019.115088
Corynespora cassiicola Corynespora cassiicola Efficacy 93.53 % 10.1021/jf303807a
Corynespora cassiicola Corynespora cassiicola GI 83.88 % 10.1016/j.bmcl.2011.09.068
Corynespora cassiicola Corynespora cassiicola Inhibition 86.43 % 10.1016/j.ejmech.2009.01.012
Cucumis sativus Cucumis sativus Activity 116.0 None 10.1021/jf072816q
Cucumis sativus Cucumis sativus Activity 229.0 None 10.1021/jf072816q
Cucumis sativus Cucumis sativus Activity 268.0 None 10.1021/jf072816q
Cucumis sativus Cucumis sativus Activity 5420.0 cpm 10.1021/jf072816q
Cucumis sativus Cucumis sativus Activity 10667.0 cpm 10.1021/jf072816q
Cucumis sativus Cucumis sativus Activity 12506.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 13.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 26.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 60.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 63.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 73.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 679.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 1323.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 1409.0 None 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 3033.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 3195.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 3731.0 cpm 10.1021/jf072816q
Cucurbita pepo Cucurbita pepo Activity 71701.0 cpm 10.1021/jf072816q
Curvularia lunata Curvularia lunata MIC 125.0 ug.mL-1 10.1016/j.bmc.2019.115088
Cytospora Cytospora MIC 62.5 ug.mL-1 10.1016/j.bmc.2019.115088
Diplodia mutila Diplodia mutila EC50 0.258 mgAi/L 10.1002/ps.2309
Diplodia mutila Diplodia mutila EC50 1.35 mgAi/L 10.1002/ps.2309
Equus caballus Ferritin light chain Potency 15848.9 nM None
Escherichia coli Escherichia coli IZ 18.5 mm 10.1016/j.bmcl.2013.08.068
Escherichia coli Escherichia coli IZ nan None 10.1016/j.bmcl.2013.02.033
Escherichia coli Escherichia coli MIC 0.5 ug.mL-1 10.1016/j.bmcl.2013.08.068
Fulvia fulva Fulvia fulva Activity 43.2 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 48.4 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 73.4 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 84.4 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 91.0 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 95.2 % 10.1016/j.cropro.2006.08.005
Fulvia fulva Fulvia fulva Activity 96.5 % 10.1016/j.cropro.2006.08.005
Fusarium fujikuroi Fusarium fujikuroi Inhibition 75.4 % 10.1016/j.ejmech.2019.02.002
Fusarium oxysporum Fusarium oxysporum MIC 52.0 ug.mL-1 10.1016/j.bmc.2012.04.045
Fusarium oxysporum Fusarium oxysporum MIC 62.5 ug.mL-1 10.1016/j.bmc.2019.115088
Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum MIC 250.0 ug.mL-1 10.1016/j.bmc.2019.115088
Glycine max Glycine max Activity 91.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 134.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 136.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 160.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 172.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 324.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 797.0 None 10.1021/jf072816q
Glycine max Glycine max Activity 4613.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 6823.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 6932.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 8163.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 8753.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 16472.0 cpm 10.1021/jf072816q
Glycine max Glycine max Activity 40547.0 cpm 10.1021/jf072816q
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 2511.9 nM None
Homo sapiens 78 kDa glucose-regulated protein Potency 3981.1 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 44668.4 nM None
Homo sapiens Alpha-synuclein Potency 1412.5 nM None
Homo sapiens Androgen Receptor Potency 3162.3 nM None
Homo sapiens Androgen Receptor Potency 7079.5 nM None
Homo sapiens Arachidonate 15-lipoxygenase, type II Potency 31622.8 nM None
Homo sapiens Aryl hydrocarbon receptor Potency 12589.3 nM None
Homo sapiens Bile acid receptor FXR Potency 14125.4 nM None
Homo sapiens Bile acid receptor FXR Potency 22387.2 nM None
Homo sapiens Cellular tumor antigen p53 Potency 3981.1 nM None
Homo sapiens Cellular tumor antigen p53 Potency 6309.6 nM None
Homo sapiens Cellular tumor antigen p53 Potency 12589.3 nM None
Homo sapiens Cytochrome P450 3A4 Potency 3162.3 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 631.0 nM None
Homo sapiens DNA polymerase iota Potency 1584.9 nM None
Homo sapiens Estrogen receptor alpha Potency 14125.4 nM None
Homo sapiens Estrogen receptor alpha Potency 44668.4 nM None
Homo sapiens Glucocorticoid receptor Potency 10000.0 nM None
Homo sapiens Glucocorticoid receptor Potency 35481.3 nM None
Homo sapiens HepG2 Potency 316.2 nM None
Homo sapiens MAP kinase ERK2 Potency 1995.3 nM None
Homo sapiens MAP kinase ERK2 Potency 2238.7 nM None
Homo sapiens MAP kinase ERK2 Potency 3981.1 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 25118.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 1778.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 2238.7 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 251.2 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 19331.2 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 28183.8 nM None
Homo sapiens Peroxisome proliferator-activated receptor delta Potency 11220.2 nM None
Homo sapiens Peroxisome proliferator-activated receptor delta Potency 12589.3 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma Potency 3981.1 nM None
Homo sapiens Retinoid X receptor alpha Potency 5011.9 nM None
Homo sapiens Retinoid X receptor alpha Potency 7079.5 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 92.97 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 81.58 % 10.1124/mol.112.084152
Homo sapiens Survival motor neuron protein Potency 5011.9 nM None
Homo sapiens Thyroid hormone receptor beta-1 Potency 2511.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 25.1 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 177.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 517.4 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 651.3 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 10000.0 nM None
Homo sapiens Vitamin D receptor Potency 794.3 nM None
Homo sapiens Vitamin D receptor Potency 19952.6 nM None
Homo sapiens Vitamin D receptor Potency 70794.6 nM None
Macrophomina phaseolina Macrophomina phaseolina ED50 0.61 mg.kg-1 10.1016/j.cropro.2011.12.015
Macrophomina phaseolina Macrophomina phaseolina MIC 52.0 ug.mL-1 10.1016/j.bmc.2012.04.045
Mus musculus Nuclear receptor ROR-gamma Potency 1778.3 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 2511.9 nM None
Neofusicoccum australe Neofusicoccum australe EC50 3.847 mgAi/L 10.1002/ps.2309
Neofusicoccum australe Neofusicoccum australe EC50 10.79 mgAi/L 10.1002/ps.2309
Neofusicoccum luteum Neofusicoccum luteum Activity 30.0 % 10.1002/ps.2309
Neofusicoccum luteum Neofusicoccum luteum Activity 51.9 mm 10.1002/ps.2309
Neofusicoccum luteum Neofusicoccum luteum EC50 7.873 mgAi/L 10.1002/ps.2309
Neofusicoccum luteum Neofusicoccum luteum EC50 11.15 mgAi/L 10.1002/ps.2309
Penicillium citrinum Penicillium citrinum MIC 15.63 ug.mL-1 10.1016/j.bmc.2019.115088
Pestalotiopsis microspora Pestalotiopsis microspora EC50 2.08 ug.mL-1 10.1016/j.cropro.2012.07.018
Pestalotiopsis microspora Pestalotiopsis microspora EC50 3.05 ug.mL-1 10.1016/j.cropro.2012.07.018
Phaseolus vulgaris Phaseolus vulgaris Activity 81.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 127.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 145.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 164.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 169.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 174.0 None 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 2814.0 cpm 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 4410.0 cpm 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 5038.0 cpm 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 5697.0 cpm 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 5901.0 cpm 10.1021/jf072816q
Phaseolus vulgaris Phaseolus vulgaris Activity 6051.0 cpm 10.1021/jf072816q
Phomopsis asparagi Phomopsis asparagi EC50 4.35 ug.mL-1 10.1021/jf903665f
Phytophthora capsici Phytophthora capsici Inhibition 80.8 % 10.1016/j.ejmech.2019.02.002
Phytophthora infestans Phytophthora infestans Activity 95.0 % 10.1016/S0261-2194(00)00172-1
Phytophthora infestans Phytophthora infestans Activity 95.0 % 10.1021/jf0210369
Phytophthora infestans Phytophthora infestans Efficacy 94.0 % 10.1021/jf900674y
Phytophthora infestans Phytophthora infestans Efficacy 100.0 % 10.1021/jf900674y
Phytophthora parasitica Phytophthora parasitica Inhibition 63.71 % 10.3390/molecules16118945
Plurivorosphaerella nawae Plurivorosphaerella nawae EC50 17.0 ug.mL-1 10.1016/j.cropro.2011.05.017
Plurivorosphaerella nawae Plurivorosphaerella nawae EC50 33.5 ug.mL-1 10.1016/j.cropro.2011.05.017
Pseudomonas aeruginosa Pseudomonas aeruginosa IZ 15.8 mm 10.1016/j.bmcl.2013.08.068
Pseudomonas aeruginosa Pseudomonas aeruginosa IZ nan None 10.1016/j.bmcl.2013.02.033
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 1.7 ug.mL-1 10.1016/j.bmcl.2013.08.068
Pseudoperonospora cubensis Pseudoperonospora cubensis Activity 55.3 % 10.1584/jpestics.27.223
Puccinia asparagi Puccinia asparagi Inhibition 82.09 % 10.3390/molecules16118945
Puccinia recondita Puccinia recondita Activity 0.0 % 10.1021/jf0210369
Puccinia triticina Puccinia triticina GI 100.0 % 10.1021/jf8031364
Pyricularia grisea Pyricularia grisea Activity 0.0 % 10.1021/jf0210369
Pyricularia oryzae Pyricularia oryzae EC50 nan None 10.1021/jf903665f
Rattus norvegicus Inositol monophosphatase 1 Potency 25118.9 nM None
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Potency 22387.2 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 281.8 nM None
Rhizoctonia solani Rhizoctonia solani Activity 0.0 % 10.1021/jf0210369
Rhizoctonia solani Rhizoctonia solani Activity 4.7 mm 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani Activity 7.6 mm 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani Activity 19.3 mm 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani Activity 30.0 mm 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani EC50 0.998 ug.mL-1 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani EC50 nan None 10.1021/jf903665f
Rhizoctonia solani Rhizoctonia solani EC90 49.42 mg/L 10.1016/j.cropro.2005.11.008
Rhizoctonia solani Rhizoctonia solani Inhibition 75.48 % 10.3390/molecules16118945
Sclerotinia sclerotiorum Sclerotinia sclerotiorum EC50 0.41 ug.mL-1 10.1021/jf903665f
Sclerotinia sclerotiorum Sclerotinia sclerotiorum EC50 7.16 ug.mL-1 10.1016/j.bmc.2008.02.048
Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition 70.0 % 10.3390/molecules16118945
Sclerotinia sclerotiorum Sclerotinia sclerotiorum Inhibition 87.6 % 10.1016/j.ejmech.2019.02.002
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Staphylococcus aureus Staphylococcus aureus IZ 14.0 mm 10.1016/j.bmcl.2013.08.068
Staphylococcus aureus Staphylococcus aureus IZ 20.1 mm 10.1016/j.bmcl.2013.02.033
Staphylococcus aureus Staphylococcus aureus MBC99.9 2.0 ug ml-1 10.1016/j.bmcl.2013.08.068
Staphylococcus aureus Staphylococcus aureus MIC 0.5 ug.mL-1 10.1016/j.bmcl.2013.02.033
Staphylococcus aureus Staphylococcus aureus MIC 1.3 ug.mL-1 10.1016/j.bmcl.2013.08.068
Trypanosoma cruzi Cruzipain Potency 39810.7 nM None
Valsa mali Valsa mali Inhibition 88.0 % 10.3390/molecules16118945
Verticillium dahliae Verticillium dahliae MIC 31.25 ug.mL-1 10.1016/j.bmc.2019.115088
Vitis vinifera Vitis vinifera Activity 36.0 None 10.1021/jf072816q
Vitis vinifera Vitis vinifera Activity 66.0 None 10.1021/jf072816q
Vitis vinifera Vitis vinifera Activity 155.0 None 10.1021/jf072816q
Vitis vinifera Vitis vinifera Activity 2201.0 cpm 10.1021/jf072816q
Vitis vinifera Vitis vinifera Activity 4015.0 cpm 10.1021/jf072816q
Vitis vinifera Vitis vinifera Activity 9447.0 cpm 10.1021/jf072816q
None Molecular identity unknown Potency 22387.2 nM None
None Molecular identity unknown Potency 70794.6 nM None
None Unchecked Potency 631.0 nM None
None Unchecked Potency 1122.0 nM None
None Unchecked Potency 2238.7 nM None
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 28183.8 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT015780 N#Cc1c(Cl)c(Cl)c(Cl)c(C#N)c1Cl.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)O)C(=O)O>>N#Cc1c(Cl)c(Cl)c(SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)c(C#N)c1Cl RXN-22465
AKRT015781 N#Cc1c(Cl)c(Cl)c(Cl)c(C#N)c1Cl>>N#Cc1c(O)c(Cl)c(Cl)c(C#N)c1Cl 65016