Development of a rice herbicide, fenoxasulfone

Fujinami, Makoto; Takahashi, Yuki; Tanetani, Yoshitaka; Ito, M.; Nasu, Mina

doi:10.1584/jpestics.j19-04

Cited by 5 publications

(6 citation statements)

References 4 publications

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“…and other annual weeds at 150-200 g a.i./ha with long residual activity. 104) Fenoxasulfone was registered in Japan in 2014, and various products containing fenoxasulfone have been launched.…”

Section: Vlcfae Inhibitorsmentioning

confidence: 99%

Development of novel pesticides in the 21st century

2020

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General trends and strategies for novel pesticides are summarized. Global pesticide sales and pesticide discovery research are also briefly reviewed. At least 105 chemical pesticides have been launched during the past decade or are under development: 43 fungicides, 34 insecticides/acaricides, 6 nematicides, 21 herbicides, and 1 herbicide safener. Most of them are safe to humans and environmentally friendly. The most developed fungicides are SDHI (succinate dehydrogenase inhibitors), DMI (demethylation inhibitors), QoI (quinone outside inhibitors), and QiI (quinone inside inhibitors). Due to the development of resistance to fungicides with existing modes of action, many fungicides possessing various novel modes of action have been launched or are under development. The trend of insecticide development is changing from organophosphorus, carbamate, and synthetic pyrethroids to nicotinic and diamide insecticides. During the past decade, compounds possessing a variety of novel modes of action have also been launched or are under development. Flupyradifurone and flupyrimin, exhibiting extremely low honeybee toxicity, have been developed and subjected to practical use. Herbicides possessing varied modes of action, such as acetolactate synthase, p-hydroxyphenylpyruvate dioxygenase, protoporphyrinogen oxidase, and very-long-chain fatty acid elongase inhibition, have been developed, but no herbicides possessing a novel mode action have commercialized in nearly 30 years. It is of interest that cyclopyrimorate, which was recently launched, and tetflupyrolimet, which is under development, have novel modes action: homogentisate solanesyltransferase (HST) and dihydroorotate dehydrogenase (DHODH) inhibition, respectively. The development of useful acaricides and nematicides is also progressing. Some natural product origin pesticides are getting attention.

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Section: Vlcfae Inhibitorsmentioning

confidence: 99%

Development of novel pesticides in the 21st century

2020

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“…Pyroxasulfone has experienced substantial growth in the marketplace for use on cereal grains, soybeans, corn, cotton, and some vegetable crops, whereas fenoxasulfone is labeled for control of Echinochloa spp. and other annual weeds in rice crops (Fujinami et al 2019). The favorable environmental attributes of isoxazolines as low-use-rate VLCFA-inhibiting herbicides with relatively fewer cases of resistant weeds has prompted discovery research efforts in the last two decades.…”

Section: The Future Of Vlcfa-inhibiting Herbicidesmentioning

confidence: 99%

“…It has long residual activity and displays herbicidal activity against Echinochloa spp. And other annual weeds at 150 to 200 g ai ha –1 (Fujinami et al 2019; Umetsu and Shirai 2020).…”

Section: Chemical Families Of Vlcfa-inhibiting Herbicidesmentioning

confidence: 99%

Very long chain fatty acid–inhibiting herbicides: Current uses, site of action, herbicide-resistant weeds, and future

Jhala,

Singh,

Shergill

et al. 2023

Weed Technol

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The herbicides that inhibit very long chain fatty acid (VLCFA) elongases are primarily used for residual weed control in corn, barley, oat, sorghum, soybean, sugarcane, certain vegetable crops, and wheat production fields in the United States. They act primarily by inhibiting shoot development of susceptible species, preventing weed emergence and growth. The objectives of this review were to summarize (1) the chemical family of VLCFA-inhibiting herbicides and their use in the United States, (2) the VLCFA biosynthesis in plants and their site of action, (3) VLCFA-inhibitor resistant weeds and their mechanism of resistance, and (4) the future of VLCFA-inhibiting herbicides. After their re-classification as group 15 herbicides to include shoot growth-inhibiting herbicides (group 8), the VLCFA-inhibiting herbicides are currently represented by eight chemical families (benzofurans, thiocarbamates, α-chloroacetamides, α-oxyacetamides, azolyl-carboxamides, isoxazolines, α-thioacetamides, and oxiranes). On average, VLCFA-inhibiting herbicides are applied once a year in both corn and soybean in the United States with acetochlor and S-metolachlor being the most-used VLCFA-inhibiting herbicides in corn and soybean, respectively. The site of action of group 15 herbicides results from inhibition of the VLCFA synthase, encoded by several fatty acid elongase (FAE1)-like genes in VLCFA elongase complex in an endoplasmic reticulum. The VLCFA synthase is a condensing enzyme, and relies on a conserved, reactive cysteinyl sulfur in active site that performs a nucleophilic attack on either the natural substrate (fatty acyl-CoA) or the herbicide. As of August 2023, 13 weed species have been documented resistant to VLCFA-inhibitor, including 11 monocot weeds and two dicot weeds (Palmer amaranth and waterhemp). The isoxazolines (pyroxasulfone and fenoxasulfone) are the most recently (2014) discovered VLCFA-inhibiting herbicides. Although the intensity of VLCFA-inhibitor-directed discovery efforts has decreased over the past decade, this biochemical pathway remains a viable mechanistic target for the discovery and valuable component of herbicide premixes.

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“…Moreover, a variety of non‐steroidal anti‐inflammatory drugs, [2] antibiotics (e. g. cloxacillin, 2 ), [3] as well as some promising candidates for immuno‐ and chemo‐therapeutics feature isoxazol(in)es [4] . In the field of agrochemicals, isoxazoles and isoxazolines find frequently application as herbicides (fenoxasulfone, 3 ), [5] fungicides (hymexazol, 4 ), [6] and insecticides (fluxametamid, 5 ) [7] …”

Section: Introductionmentioning

confidence: 99%

“…[1] Moreover, a variety of non-steroidal antiinflammatory drugs, [2] antibiotics (e. g. cloxacillin, 2), [3] as well as some promising candidates for immuno-and chemo-therapeutics feature isoxazol(in)es. [4] In the field of agrochemicals, isoxazoles and isoxazolines find frequently application as herbicides (fenoxasulfone, 3), [5] fungicides (hymexazol, 4), [6] and insecticides (fluxametamid, 5). [7] Conventionally, isoxazoles and isoxazolines can be accessed via intramolecular oxidative cyclization of allyl aldehyde oximes, [8] propargyl hydroxylamines [9] or propargyl aldehyde oximes.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Isoxazoles and Isoxazolines via Anodic Oxidation of Oximes

Hofmann,

Winter,

Prenzel

et al. 2023

ChemElectroChem

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Isoxazol(in)es are widely featured structural motifs in natural products, agrochemicals, and pharmaceuticals. The first intermolecular approach for a direct electrochemical synthesis from readily available aldoximes is reported. Isoxazoles and isoxazolines were obtained in yields up to 81 %. The synthesis is carried out in an undivided cell as the simplest electrochemical set‐up and requires only the use of electric current as traceless oxidizing agent. The application of inexpensive and widely available electrode materials in combination with recyclable supporting electrolytes and solvents paves the path for translation of the presented reaction onto preparative scale. This is underlined by successful scale‐up to multi‐gram runs.

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Development of a rice herbicide, fenoxasulfone

Cited by 5 publications

References 4 publications

Development of novel pesticides in the 21st century

Development of novel pesticides in the 21st century

Very long chain fatty acid–inhibiting herbicides: Current uses, site of action, herbicide-resistant weeds, and future

Electrochemical Synthesis of Isoxazoles and Isoxazolines via Anodic Oxidation of Oximes

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