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Literature summary extracted from

  • Lee, W.; Kwon, Y.; Lee, K.; Choi, J.; Seu, Y.
    Synthesis of cyclopropyl ester and amide substituted pyrimidinediones as protoporphyrinogen oxidase-inhibiting herbicides (2021), Bull. Korean Chem. Soc., 42, 420-428 .
No PubMed abstract available

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.3.4 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 butafenacil
-
 Chenopodium album
1.3.3.4 butafenacil
-
 Digitaria sanguinalis
1.3.3.4 butafenacil
-
 Dinebra chinensis
1.3.3.4 butafenacil
-
 Echinochloa crus-galli
1.3.3.4 butafenacil
-
 Galinsoga quadriradiata
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimid in-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimid in-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimid in-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 ethyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyr imidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)acetyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 isopropyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)alanyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)alanyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)alanyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)glycyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)glycyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidi n-1(2H)-yl)phenyl)glycyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)alanyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)alanyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)glycyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 methyl 2-(1-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)glycyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetamide
-
 Chenopodium album
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetamide
-
 Dinebra chinensis
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrim idin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetamide
-
 Galinsoga quadriradiata
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetamide
-
 Digitaria sanguinalis
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetamide
-
 Echinochloa crus-galli
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 methyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 propyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimi din-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Chenopodium album
1.3.3.4 propyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimi din-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Dinebra chinensis
1.3.3.4 propyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimi din-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Galinsoga quadriradiata
1.3.3.4 propyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Digitaria sanguinalis
1.3.3.4 propyl 2-(1-(((2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)thio)propanoyl)thio)methyl)cyclopropyl)acetate
-
 Echinochloa crus-galli
1.3.3.4 saflufenacil
-
 Chenopodium album
1.3.3.4 saflufenacil
-
 Digitaria sanguinalis
1.3.3.4 saflufenacil
-
 Dinebra chinensis
1.3.3.4 saflufenacil
-
 Echinochloa crus-galli
1.3.3.4 saflufenacil
-
 Galinsoga quadriradiata
1.3.3.4 tiafenacil
-
 Chenopodium album
1.3.3.4 tiafenacil
-
 Digitaria sanguinalis
1.3.3.4 tiafenacil
-
 Dinebra chinensis
1.3.3.4 tiafenacil
-
 Echinochloa crus-galli
1.3.3.4 tiafenacil
-
 Galinsoga quadriradiata

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 Echinochloa crus-galli
-
 protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2 Digitaria sanguinalis
-
 protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2 Chenopodium album
-
 protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2 Dinebra chinensis
-
 protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2 Galinsoga quadriradiata
-
 protoporphyrin IX + 3 H2O2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.3.3.4 Chenopodium album
-
-
-
1.3.3.4 Digitaria sanguinalis
-
-
-
1.3.3.4 Dinebra chinensis
-
-
-
1.3.3.4 Echinochloa crus-galli
-
-
-
1.3.3.4 Galinsoga quadriradiata
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Echinochloa crus-galli protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Digitaria sanguinalis protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Chenopodium album protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Dinebra chinensis protoporphyrin IX + 3 H2O2
-
 ?
1.3.3.4 protoporphyrinogen IX + 3 O2
-
 Galinsoga quadriradiata protoporphyrin IX + 3 H2O2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.3.4 PPO
-
 Echinochloa crus-galli
1.3.3.4 PPO
-
 Digitaria sanguinalis
1.3.3.4 PPO
-
 Chenopodium album
1.3.3.4 PPO
-
 Dinebra chinensis
1.3.3.4 PPO
-
 Galinsoga quadriradiata
1.3.3.4 protoporphyrinogen oxidase
-
 Echinochloa crus-galli
1.3.3.4 protoporphyrinogen oxidase
-
 Digitaria sanguinalis
1.3.3.4 protoporphyrinogen oxidase
-
 Chenopodium album
1.3.3.4 protoporphyrinogen oxidase
-
 Dinebra chinensis
1.3.3.4 protoporphyrinogen oxidase
-
 Galinsoga quadriradiata