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Literature summary for 1.3.3.4 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

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

Inhibitors

Inhibitors Comment Organism Structure
1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[2-(allylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[2-(allylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[2-(butylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[2-(butylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[6-chloro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[6-chloro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[6-fluoro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
Nicotiana tabacum
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
sulfentrazone
-
Nicotiana tabacum

Localization

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Nicotiana tabacum
-
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
PPO
-
Nicotiana tabacum

Temperature Optimum [°C]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
FAD
-
Nicotiana tabacum

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00003
-
sulfentrazone pH 7.5, 22°C, recombinant enzyme Nicotiana tabacum
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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