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Literature summary extracted from

  • Wei, W.; Zhou, S.; Cheng, D.; Li, Y.; Liu, J.; Xie, Y.; Li, Y.; Li, Z.
    Design, synthesis and herbicidal activity study of aryl 2,6-disubstituted sulfonylureas as potent acetohydroxyacid synthase inhibitors (2017), Bioorg. Med. Chem. Lett., 27, 3365-3369 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.2.1.6 2-bromo-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-bromo-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 67.5% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-bromo-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-bromo-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-bromo-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 68.9% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 64.8% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 69.9% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 68.2% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 62.2% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 64.1% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 62.2% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-chloro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-chloro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 67.7% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-chloro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-chloro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-chloro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 44.5% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 67.9% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-fluoro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-fluoro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 72.6% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-fluoro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-fluoro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-fluoro-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 68.9% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 2-iodo-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 2-iodo-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide 68.5% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 2-iodo-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 2-iodo-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 2-iodo-N-[(4-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 chlorsulfuron
-
Amaranthus retroflexus
2.2.1.6 chlorsulfuron
-
Arabidopsis thaliana
2.2.1.6 chlorsulfuron
-
Brassica napus
2.2.1.6 chlorsulfuron
-
Digitaria adscendens
2.2.1.6 chlorsulfuron
-
Echinochloa crus-galli
2.2.1.6 monosulfuron
-
Amaranthus retroflexus
2.2.1.6 monosulfuron
-
Arabidopsis thaliana
2.2.1.6 monosulfuron
-
Brassica napus
2.2.1.6 monosulfuron
-
Digitaria adscendens
2.2.1.6 monosulfuron
-
Echinochloa crus-galli
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide 68.4% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide 65.1% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide
-
Brassica napus
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide
-
Digitaria adscendens
2.2.1.6 N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide
-
Echinochloa crus-galli
2.2.1.6 N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide
-
Amaranthus retroflexus
2.2.1.6 N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide 65.1% inhibition at 10 mg/l Arabidopsis thaliana
2.2.1.6 N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide
-
Brassica napus
2.2.1.6 N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide
-
Digitaria adscendens
2.2.1.6 N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide
-
Echinochloa crus-galli

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.2.1.6 2 pyruvate Arabidopsis thaliana
-
2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate Brassica napus
-
2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate Echinochloa crus-galli
-
2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate Amaranthus retroflexus
-
2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate Digitaria adscendens
-
2-acetolactate + CO2
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.2.1.6 Amaranthus retroflexus
-
-
-
2.2.1.6 Arabidopsis thaliana
-
-
-
2.2.1.6 Brassica napus
-
-
-
2.2.1.6 Digitaria adscendens
-
-
-
2.2.1.6 Echinochloa crus-galli
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.2.1.6 2 pyruvate
-
Arabidopsis thaliana 2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate
-
Brassica napus 2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate
-
Echinochloa crus-galli 2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate
-
Amaranthus retroflexus 2-acetolactate + CO2
-
?
2.2.1.6 2 pyruvate
-
Digitaria adscendens 2-acetolactate + CO2
-
?

Synonyms

EC Number Synonyms Comment Organism
2.2.1.6 acetohydroxyacid synthase
-
Arabidopsis thaliana
2.2.1.6 acetohydroxyacid synthase
-
Brassica napus
2.2.1.6 acetohydroxyacid synthase
-
Echinochloa crus-galli
2.2.1.6 acetohydroxyacid synthase
-
Amaranthus retroflexus
2.2.1.6 acetohydroxyacid synthase
-
Digitaria adscendens
2.2.1.6 AHAS
-
Arabidopsis thaliana
2.2.1.6 AHAS
-
Brassica napus
2.2.1.6 AHAS
-
Echinochloa crus-galli
2.2.1.6 AHAS
-
Amaranthus retroflexus
2.2.1.6 AHAS
-
Digitaria adscendens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.2.1.6 0.0000115
-
2-fluoro-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0000153
-
2-bromo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0000229
-
2-iodo-N-[(4-methoxy-6-methylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0000283
-
N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-fluoro-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0000524
-
chlorsulfuron apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0001127
-
N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-2-iodo-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0001658
-
N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-2-nitro-6-(2,2,2-trifluoroethoxy)benzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana
2.2.1.6 0.0001729
-
2-chloro-N-[(4,6-dimethylpyrimidin-2-yl)carbamoyl]-6-nitrobenzenesulfonamide apparent value, pH and temperature not specified in the publication Arabidopsis thaliana