Protoporphyrinogen IX Oxidase Inhibitors

Theodoridis, George; Liebl, Rex A.; Žagar, Cyrill

doi:10.1002/9783527644179.ch3

Cited by 20 publications

(9 citation statements)

References 62 publications

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“…Most of the major industrial companies involved in agrochemical research in the 1980s had a programme devoted to protoporphyrinogen‐IX‐oxidase inhibitors, at that time a new class of herbicides . Some analogues made in this context had not only herbicidal activity but also weak insecticidal activity.…”

Section: Methodsmentioning

confidence: 99%

The story of a new insecticidal chemistry class: the diamides

Jeanguenat

2012

Pest Management Science

146

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This paper describes the story of the invention of the diamides, a novel chemical class of insecticides. It starts with the pioneering work by Nihon Nohyaku researchers, who developed a herbicide lead with weak insecticidal activity to flubendiamide, a highly potent lepidoptericide. The journey continues with Nissan's isoxazolines and the invention of the anthranilamides by DuPont, culminating in the discovery of the blockbuster chlorantraniliprole and its analogue cyantraniliprole. The next steps are Syngenta's sulfoximines and bicyclic anthranilamides, Ishihara Sangyo Kaisha's cyclopropylamides, Sumitomo's hydrazides, Bayer's pyrazoles and tetrazoles, BASF's sulfoximines and more recent contributions from Chinese agrochemical companies and academic institutions. The diamides affect calcium homeostasis by binding to ryanodine receptors and releasing calcium from the intracellular stores. Investigations at Nihon Nohyaku, DuPont and Bayer on the action of the diamides on ryanodine receptors will be briefly reported.

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Section: Methodsmentioning

confidence: 99%

The story of a new insecticidal chemistry class: the diamides

Jeanguenat

2012

Pest Management Science

146

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“…It has been demonstrated that all of the known Protox inhibitors apparently mimic parts structure of the substrate protoporphyrinogen IX and compete with protogen at or near the catalytic site on the enzyme . In contrast to other herbicides, PPO inhibitors are sharing several advantages such as low toxicity, low use‐rate, broad spectrum herbicidal activities, quick onset of action, long‐lasting effect, and other environmentally benign characteristics . Notably, the most unique property of PPO inhibitors lies in the much lower resistant development rate compared with herbicides with other mode of action such as acetolactate synthase (ALS) inhibitors.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, In Vitro Protoporphyrinogen Oxidase Inhibition, and Herbicidal Activity of N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindole‐1,3‐diones and N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindol‐1‐ones

Jiang

Zuo

et al. 2014

Chem Biol Drug Des

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Protoporphyrinogen oxidase (EC 1.3.3.4) is one of the most significant targets for a large family of herbicides. As part of our continuous efforts to search for novel protoporphyrinogen oxidase-inhibiting herbicides, N-(benzothiazol-5-yl)tetrahydroisoindole-1,3-dione was selected as a lead compound for structural optimization, leading to the syntheses of a series of novel N-(benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones (1a-o) and N-(benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones (2a-i). These newly prepared compounds were characterized by elemental analyses, (1) H NMR, and ESI-MS, and the structures of 1h and 2h were further confirmed by X-ray diffraction analyses. The bioassays indicated that some compounds displayed comparable or higher protoporphyrinogen oxidase inhibition activities in comparison with the commercial control. Very promising, compound 2a, ethyl 2-((6-fluoro-5-(4,5,6,7-tetrahydro-1-oxo-1H-isoindol-2(3H)-yl)benzo[d]thiazol-2-yl)-sulfanyl)acetate, was recognized as the most potent candidate with K(i) value of 0.0091 μm. Further greenhouse screening results demonstrated that some compounds exhibited good herbicidal activity against Chenopodium album at the dosage of 150 g/ha.

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“…The inhibition of protoporphyrinogen‐IX‐oxidase leads to accumulation of the enzyme product protoporphyrin IX. Light induces protoporphyrin IX to generate large amounts of singlet oxygen, leading to the peroxidation of the unsaturated bond of the fatty acids found in cell membranes . With the success of herbicide‐resistant crops and the possibility of post‐emergence applications combined with relatively low herbicide costs, combined with the perceived advantage of applying a herbicide only when weed growth was observed, the end of residual herbicides was prophesied to have arrived a while ago .…”

Section: Herbicides For Weed Controlmentioning

confidence: 99%

Progress of modern agricultural chemistry and future prospects

2015

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Agriculture is facing an enormous challenge: it must ensure that enough high-quality food is available to meet the needs of a continually growing population. Current and future agronomic production of food, feed, fuel and fibre requires innovative solutions for existing and future challenges, such as climate change, resistance to pests, increased regulatory demands, renewable raw materials or requirements resulting from food chain partnerships. Modern agricultural chemistry has to support farmers to manage these tasks. Today, the so-called 'side effects' of agrochemicals regarding yield and quality are gaining more importance. Agrochemical companies with a strong research and development focus will have the opportunity to shape the future of agriculture by delivering innovative integrated solutions. This review gives a comprehensive overview of the innovative products launched over the past 10 years and describes the progress of modern agricultural chemistry and its future prospects.

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Protoporphyrinogen IX Oxidase Inhibitors

Cited by 20 publications

References 62 publications

The story of a new insecticidal chemistry class: the diamides

The story of a new insecticidal chemistry class: the diamides

Synthesis, In Vitro Protoporphyrinogen Oxidase Inhibition, and Herbicidal Activity of N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindole‐1,3‐diones and N‐(Benzothiazol‐5‐yl)hexahydro‐1H‐isoindol‐1‐ones

Progress of modern agricultural chemistry and future prospects

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