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Literature summary extracted from

  • Yang, Z.; Sheng-Gang, Y.; Yan-Ping, L.; Ying, T.; Ge-Fei, H.; Qiong-You, W.; Zhen, X.; Guang-Fu, Y.
    Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors (2013), Bioorg. Med. Chem., 21, 3245-3255.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.3.3.4 agriculture protoporphyrinogen oxidase is the action target for several structurally diverse herbicides Nicotiana tabacum

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.3.4 1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[2-(allylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[2-(allylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[2-(butylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[2-(butylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[6-chloro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[6-chloro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[6-fluoro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
 Nicotiana tabacum
1.3.3.4 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]acetic acid
-
 Nicotiana tabacum
1.3.3.4 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]propanoic acid
-
 Nicotiana tabacum
1.3.3.4 2-[6-bromo-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
-
 Nicotiana tabacum
1.3.3.4 2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]acetic acid
-
 Nicotiana tabacum
1.3.3.4 2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]propanoic acid
-
 Nicotiana tabacum
1.3.3.4 3-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-ylthio]propanoic acid
-
 Nicotiana tabacum
1.3.3.4 3-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-ylthio]propanoic acid
-
 Nicotiana tabacum
1.3.3.4 ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]acetate
-
 Nicotiana tabacum
1.3.3.4 ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]propanoate
-
 Nicotiana tabacum
1.3.3.4 ethyl 1-[6-bromo-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
 Nicotiana tabacum
1.3.3.4 ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
 Nicotiana tabacum
1.3.3.4 ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]propanoate
-
 Nicotiana tabacum
1.3.3.4 methyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
 Nicotiana tabacum
1.3.3.4 methyl 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluoro benzothiazol-2-ylthio]acetate
-
 Nicotiana tabacum
1.3.3.4 additional information design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors, structure-activity relationships, computational simulations and binding free energy calculations, and herbicidal activities of the compounds against weeds, overview. The substituents, e.g. F, Cl, and Br, on position 2 affect the bioactive conformation of inhibitors. No inhibition by S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-methyl carbonothioate and S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-ethyl carbonothioate Nicotiana tabacum
1.3.3.4 S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-ethyl carbonothioate
-
 Nicotiana tabacum
1.3.3.4 S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-methyl carbonothioate
-
 Nicotiana tabacum
1.3.3.4 S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-ethyl carbonothioate
-
 Nicotiana tabacum
1.3.3.4 S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-methyl carbonothioate
-
 Nicotiana tabacum
1.3.3.4 sulfentrazone
-
 Nicotiana tabacum

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.3.3.4 mitochondrion
-
 Nicotiana tabacum 5739
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.3.3.4 protoporphyrinogen IX + 3 O2 Nicotiana tabacum
-
 protoporphyrin IX + 3 H2O2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.3.3.4 Nicotiana tabacum
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Nicotiana tabacum protoporphyrin IX + 3 H2O2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.3.4 PPO
-
 Nicotiana tabacum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.3.3.4 22
-
 assay at room temperature Nicotiana tabacum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.3.3.4 7.5
-
 assay at Nicotiana tabacum

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.3.4 FAD
-
 Nicotiana tabacum

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.3.3.4 0.00003
-
 sulfentrazone pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00006
-
 ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]acetate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.0002
-
 1-[2-(allylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00021
-
 1-[2-(butylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00024
-
 ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]propanoate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00029
-
 S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-methyl carbonothioate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.0003
-
 1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00051
-
 1-[6-fluoro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00058
-
 S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-ethyl carbonothioate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00108
-
 methyl 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluoro benzothiazol-2-ylthio]acetate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00121
-
 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]propanoic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00137
-
 ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00152
-
 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]acetic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00167
-
 3-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-ylthio]propanoic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00201
-
 1-[6-chloro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00297
-
 1-[2-(butylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00313
-
 1-[2-(allylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00339
-
 ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]propanoate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.00673
-
 2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]propanoic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.008
-
 ethyl 1-[6-bromo-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.01026
-
 2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]acetic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.01278
-
 1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.01386
-
 1-[6-chloro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.01518
-
 methyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
1.3.3.4 0.01779
-
 3-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-ylthio]propanoic acid pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum