Mode for Herbicidal Action of 2-Amino-3-chloro-1,4-naphthoquinone (ACN)

Koura, Seigo; Takasuka, Kiyoshi; Katsuyama, Noriyoshi; Ogino, Chifuyu; Sato, Yukiharu; Wakabayashi, Katsunori

doi:10.1271/bbb.58.1210

Cited by 4 publications

(3 citation statements)

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“…The following is the mechanism of herbicidal action for each herbicide: ACN, inhibition of porphyrin biosynthesis (Koura et al 1994); Daimuron, inhibition of seminal root elongation (Ogasawara et al 1991); Cafenstrole, inhibition of elongation at the growing point (Kanzaki et al 2001); Azimsulfuron, inhibition of acetolactate synthase (ALS), which is involved in biosynthesis of branched-chain amino acids (Shirakura et al 1995); Cyhalofop-butyl, inhibition of fatty acid synthesis by activity inhibition of acetyl-CoA carboxylase (ACCase) (Ito et al 1998); Bensulfuron-methyl: inhibition of ALS, which is involved in biosynthesis of branched-chain amino acids (Yuyama et al 1987).…”

Section: à2mentioning

confidence: 99%

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Usui

Kasubuchi

2011

Soil Science and Plant Nutrition

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Section: à2mentioning

confidence: 99%

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Usui

Kasubuchi

2011

Soil Science and Plant Nutrition

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“…3), the observed bleaching is thought to be due to the action of quinoclamine. Quinoclamine has been shown to inhibit chlorophyll synthesis (Koura et al, 1994), but mechanisms of phototoxicity have not been clarified. Even if chlorophyll synthesis can be inhibited by Kiredar treatment in some cases, it is likely that such inhibition was not a major cause of ejecting algal cells, considering the lack of obvious reduction in algal cells ejected by A. atodai (see Supplementary Figure S2).…”

Section: Bleaching Of Sea Anemones By Quinoclaminementioning

confidence: 99%

Establishment of a New Model Sea Anemone for Comparative Studies on Cnidarian-Algal Symbiosis

et al. 2023

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Frequent coral bleaching has drawn attention to the mechanisms of coral dinoflagellate endosymbiosis. Owing to the difficulty of rearing corals in the laboratory, model symbiosis systems are desired. The sea anemone Exaiptasia diaphana, hosting clade B1 of the genus Breviolum, has long been studied as a model system; however, a single species is insufficient for comparative studies and thus provides only limited resources for symbiosis research, especially regarding the specificity of host-symbiont associations. We established a clonal strain of the sea anemone Anthopleura atodai, whose symbiont was identified as a novel subclade of Symbiodinium (clade A) using a novel feeding method. We also developed a method to efficiently bleach various sea anemone species using a quinoclamine-based herbicide. Bleached A. atodai polyps were vital and able to reproduce asexually, exhibiting no signs of harmful effects of the drug treatment. Pilot studies have suggested that host-symbiont specificity is influenced by multiple steps differently in A. atodai and E. diaphana. RNAseq analyses of A. atodai showed that multiple NPC2 genes were expressed in the symbiotic state, which have been suggested to function in the transport of sterols from symbionts to host cells. These results reveal the usefulness of A. atodai in comparative studies of cnidarian-algal symbiosis.

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“…Quinone motifs are common in plants, animals, fungi, and bacteria. , Presently, researchers are showing interest in synthesizing 2-amino-1,4-naphthoquinones due to their wide range of biological properties such as antitumor, , antimalarial, − antiseizure, antifilarial, antimicrobial, , antibacterial, , anticancer, − herbicide, , and fungicide . These biological and pharmacological activities have made synthesizing these compounds more appealing.…”

Section: Introductionmentioning

confidence: 99%

Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp²)–H and N–H Bonds: Amination of Naphthoquinones with Amines

2023

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Herein, we report a blue-light-driven amination of C(sp 2)–H bond of naphthoquinones and quinones with the N–H bond of primary and secondary amines for the synthesis of 2-amino-naphthoquinones and 2-amino-quinones. The coupling of naphthoquinones with a wide array of aliphatic, aromatic, chiral, primary, and secondary amines having electron donating (−CH3, −OCH3, −SCH3), withdrawing (−F, −Cl, −Br, −I), and CO2H, −OH, −NH2 groups with acidic protons selectively occurred to afford C–N coupled 2-amino-naphthoquinones in 60–99% yields and hydrogen gas as a byproduct in methanol solvent without using any additional reagents, additives, and oxidant under the blue light irradiation. Mechanistic insight by DFT computation, controlled experiments, kinetic isotopic effect, and substitution effect of the substrates suggest that the reaction proceeds by radical pathway in which naphthoquinone forms a highly oxidizing naphthoquinonyl biradical upon irradiation of blue light (457 nm). Consequently, electron transfer from electron-rich amine to an oxidizing naphthoquinonyl biradical leads to a naphthoquinonyl radical anion and aminyl radical cation, followed by proton transfer and delocalization leading to a carbon-centered naphthoquinonyl radical. The cross-coupling of naphthoquinonyl carbon-centered and aminyl nitrogen radicals forms a C–N bond, with subsequent elimination of hydrogen gas (which was also confirmed by GC-TCD), affording 2-amino-1,4-naphthoquinone under metal-, reagent-, base-, and oxidant-free conditions.

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Mode for Herbicidal Action of 2-Amino-3-chloro-1,4-naphthoquinone (ACN)

Cited by 4 publications

References 0 publications

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Establishment of a New Model Sea Anemone for Comparative Studies on Cnidarian-Algal Symbiosis

Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp²)–H and N–H Bonds: Amination of Naphthoquinones with Amines

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Mode for Herbicidal Action of 2-Amino-3-chloro-1,4-naphthoquinone (ACN)

Cited by 4 publications

References 0 publications

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Effects of herbicide application on carbon dioxide, dissolved oxygen, pH, and RpH in paddy-field ponded water

Establishment of a New Model Sea Anemone for Comparative Studies on Cnidarian-Algal Symbiosis

Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp2)–H and N–H Bonds: Amination of Naphthoquinones with Amines

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Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp²)–H and N–H Bonds: Amination of Naphthoquinones with Amines