Synthesis and Phytotoxic Activities of N-Substituted Phenyl Isothiazolone Derivatives

Miyamoto, Yoshiko; Ikeda, Yoshiki; Wakabayashi, Katsunori

doi:10.1584/jpestics.28.293

Cited by 5 publications

(2 citation statements)

References 7 publications

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“…3.21). The 2-(4-chloro-3-isopropoxycarbonyl)phenyl isothiazole-1,1-dioxide 83 was the most active in the isothiazolone series as measured by inhibition of protoporphyrinogen IX oxidase isolated from corn, as well as by growth inhibition, chlorophyll decrease, and peroxidative destruction of cell membranes of green microalga Scenedesmus acutus [94]. Compound 83 was more active than either compound 81 or 82, but about 100Â weaker than the reference compound 80.…”

Section: Recent Developmentsmentioning

confidence: 97%

Protoporphyrinogen‐IX‐oxidase Inhibitors

Theodoridis

Liebl

Žagar

2007

Modern Crop Protection Compounds

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Section: Recent Developmentsmentioning

confidence: 97%

Protoporphyrinogen‐IX‐oxidase Inhibitors

Theodoridis

Liebl

Žagar

2007

Modern Crop Protection Compounds

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“…Thousands of active compounds exhibiting this mode of action have been synthesized (1)(2)(3)(4)(5). On the basis of their chemical structures, these compounds can be classified as diphenyl ethers (6,7), benzoxazinones (8), phenyl imides (9)(10)(11)(12), triazolinones (13), tetrazolinones (14), oxadiazolones (15), thiadiazolidines (16), isothiazolones (17), and arylpyrroles (18). 2-(7-Fluoro-3-oxo-3,4-dihydro-2H-benzo-[b] [1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-2H-isoindoline-1,3-diones are a class of phenylimide protoxinhibiting herbicides (19,20).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Herbicidal Activity of 2-(7-Fluoro-3-oxo- 3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-diones

Huang

Ren

et al. 2005

J. Agric. Food Chem.

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The mode of action of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-2H-isoindoline-1,3-diones, including the commercial herbicide flumioxazin, had been identified as inhibition of protoporphyrinogen oxidase (protox). As part of continuous efforts to search for new herbicides with high efficacy, broad-spectrum activity, and safety to crops, flumioxazin and its iodo analogue (B2055) were used as lead compounds for further optimization. Series of novel compounds were prepared by multistep synthetic procedures starting from 5-fluoro-2-nitrophenol. All of the test compounds were structurally confirmed by 1H NMR, IR, mass spectroscopy, and elemental analysis. Preliminary bioassay data showed that some of them possess commercial levels of herbicidal activity comparable to those of other protox-inhibiting herbicides. One of the best compounds, 5-fluoro-2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-dione (8e), has IC50 values for velvetleaf (Abutilon theophrasti Medic) and crabgrass (Digitaria sanguinalis) comparable to thos of B2055. With respect to crop selectivity, compound 8e is similar to flumioxazin. Compound 8e is safe to cotton and maize at a rate of 150 g of active ingredient (ai)/ha or less when applied at pre-emergent stage, and it has the best safety to wheat among the tested crops, showing no injury after post-emergent application at 7.5-30 g of ai/ha.

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