Application | Comment | Organism |
---|---|---|
agriculture | protoporphyrinogen oxidase is the action target for several structurally diverse herbicides | Nicotiana tabacum |
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 | Comment | Organism | GeneOntology No. | Textmining |
---|---|---|---|---|
mitochondrion | - |
Nicotiana tabacum | 5739 | - |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
protoporphyrinogen IX + 3 O2 | Nicotiana tabacum | - |
protoporphyrin IX + 3 H2O2 | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Nicotiana tabacum | - |
- |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
protoporphyrinogen IX + 3 O2 | - |
Nicotiana tabacum | protoporphyrin IX + 3 H2O2 | - |
? |
Synonyms | Comment | Organism |
---|---|---|
PPO | - |
Nicotiana tabacum |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
22 | - |
assay at room temperature | Nicotiana tabacum |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.5 | - |
assay at | Nicotiana tabacum |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
FAD | - |
Nicotiana tabacum |
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 |