Quantitative correlation between short-term accumulation of protoporphyrin IX and peroxidative activity of cyclic imides

Watanabe, Hiroyuki; Ohori, Yuji; Sandmann, Gerhard; Wakabayashi, Katsunori; Böger, Peter

doi:10.1016/0048-3575(92)90057-7

Cited by 26 publications

(20 citation statements)

References 20 publications

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“…Four phytotoxic parameters, namely Protox inhibition (pI5o (Protox)), protoporphyrin-IX accumulation, ethane formation (pI5o (Eth)) and decrease of chlorophyll contents (pI5o (Chl)), can be used conveniently to assay peroxidative activity of the compounds in autotrophic Scenedesmus cells. 9 The effects of thiadiazolidine-thiones and triazolidine-dithiones (1-18) on protoporphyrin-IX accumulation, ethane formation, decrease of chlorophyll contents and cell growth (pI5o (S)) in Scenedesmus cells were quite similar to those caused by the reference peroxidizing herbicide, oxyfluorfen. Furthermore, the selected compounds (2-9 and 11-17) strongly inhibited Protox.…”

Section: Protoporphyrin-ix Accumulation Pyotoxmentioning

confidence: 68%

Peroxidizing Phytotoxic Activity of 1, 3, 4-Thiadiazolidine-2-thiones and 1, 2, 4-Triazolidine-3, 5-dithiones

et al. 1995

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Section: Protoporphyrin-ix Accumulation Pyotoxmentioning

confidence: 68%

Peroxidizing Phytotoxic Activity of 1, 3, 4-Thiadiazolidine-2-thiones and 1, 2, 4-Triazolidine-3, 5-dithiones

et al. 1995

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“…5-100 times stronger than that of alkyl 2-chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates (3)(4)(5)(6)(7)(8)(9). The Protox inhibition, however, of the esters (3'-9') with a 4-fluorine atom at the phenyl ring were found less active than the esters (3-9) without 4-fluorine atom.…”

Section: Resultsmentioning

confidence: 99%

“…While 2-chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoic acid (2) was an about 75-fold less active Protox inhibitor than chlorophthalim (1), its alkyl esters (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were 50 to 2000 times stronger Protox inhibitors than the free acid (2). Also the reference diphenyl ether herbicide with an ester group: acifluorfen-methyl [methyl Table 1 Phytotoxic activities of 5-(3, 4 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate, 16], was found ca.…”

Section: Resultsmentioning

confidence: 99%

“…Peroxidizing Activity of Alkyl 2-chloro-5-(3, 4, 5, 6 tetrahydrophthalimido)benzoates and Alkyl 2-chloro-4 fluoro-5-(3, 4, 5, 6-tetrahydrophthalimido)-benzoates Ethane formation (PI5o (Ethane)), chlorophyll decrease (pI5o (Chlorophyll)) and growth inhibition (PI5o (Growth)) of S. acutus cells can be used conveniently to assay peroxidizing phytotoxicity of compounds. 1, 2, 4) All alkyl 2-chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and alkyl 2-chloro-4-fluoro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates (3'-9') tested caused ethane formation, chlorophyll decrease and cell-growth inhibition, as indicated by the PI5o in Table 1. The above three peroxidative phytotoxic parameters obtained were quite similar to those shown by the reference peroxidizing herbicides (1, 1' and 13-16 of Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…The phytotoxicities caused by alkyl 2-chloro-5-(3, 4, 5, 6-tetrahydro-phthalimido)benzoates (3)(4)(5)(6)(7)(8)(9)(10)(11)(12), alkyl 2-chloro-4-fluoro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates (3'-9') and eight reference peroxidizing herbicides (1, 2, 1', 2' and 13-16) were determined by inhibition of corn Protox, and light-induced ethane formation, chlorophyll decrease and growth inhibition of green microalgae S. acutus cells. The results are shown as PI5o in Tables 1 and 2.…”

Section: Resultsmentioning

confidence: 99%

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Comparison of Phytotoxicities between 4-Fluorinated and Non-fluorinated 2-Chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates

et al. 1999

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Protoporphyrinogen-IXoxidase inhibition and peroxidizing phytotoxicity were determined using a series of fluorinated and non-fluorinated alkyl 2-chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates and their parent benzoic acid derivatives. Protoporphyrinogen-IX oxidase from corn etioplasts was extracted, and ethane formation by intact cells of the green algae Scenedesmus acutus was measured. The benzoates with a fluorine atom exhibited stronger peroxidizing phytotoxicity (higher ethane formation) than the benzoates having no fluorine atom although protoporphyrinogen-IX oxidase inhibition by the fluorinated analogues was found to be weaker or almost equal to the non-fluorinated analogues. These data strengthen and generalize our previous findings with cyclic imides having an N-(4-chloro-2-fluoro-5-carboxyphenyl) group. The fluorinated analogues, which are not necessarily stronger protoporphyrinogen-IX oxidase inhibitors, exhibit stronger peroxidizing phytotoxicity with intact plant cells than those without a fluorine atom.

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Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide

et al. 1997

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: Post-emergence application of carfentrazone-ethyl at rates as low as 2É2 g ha~1 caused greater leaf injury and growth reduction in ivyleaf morningglory (Ipomoea hederacea) and velvetleaf (Abutilon theophrasti) than in soybean (Glycine max). The herbicide was more rapidly metabolized in the crop than in the weed species, with 26É7, 54É3 and 60É6% of the parent compound remaining in soybean, ivyleaf morningglory and velvetleaf, respectively, 24 h after exposure. The free acid metabolite, carfentrazone, was present in all species and accounted for 21É2È27É4% of the total radioactivity. Unknown metabolites 0 and 0É22) were four to Ðve times more abundant in soybean than in the (R f weed species. Carfentrazone-ethyl induced more leakage from leaf discs from the weeds than those from soybean and the degree of injury correlated with the amount of protoporphyrin IX (Proto IX) present in the treated tissues. Both carfentrazone-ethyl and carfentrazone were potent inhibitors of protoporphyrinogen oxidase (Protox). Therefore, the selectivity of this herbicide may, at least in part, be attributed to the lower accumulation of Proto IX in soybean than in the weeds, probably because of the ability of soybean to metabolize more carfentrazone into unknown metabolites than the weeds.

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Quantitative correlation between short-term accumulation of protoporphyrin IX and peroxidative activity of cyclic imides

Cited by 26 publications

References 20 publications

Peroxidizing Phytotoxic Activity of 1, 3, 4-Thiadiazolidine-2-thiones and 1, 2, 4-Triazolidine-3, 5-dithiones

Peroxidizing Phytotoxic Activity of 1, 3, 4-Thiadiazolidine-2-thiones and 1, 2, 4-Triazolidine-3, 5-dithiones

Comparison of Phytotoxicities between 4-Fluorinated and Non-fluorinated 2-Chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates

Selectivity and mode of action of carfentrazone-ethyl, a novel phenyl triazolinone herbicide

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