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

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 su...

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Published inWeed technology Vol. 38; no. 1; pp. 1 - 16
Main Authors Jhala, Amit J., Singh, Mandeep, Shergill, Lovreet, Singh, Rishabh, Jugulam, Mithila, Riechers, Dean E., Ganie, Zahoor A., Selby, Thomas P., Werle, Rodrigo, Norsworthy, Jason K.
Format Journal Article
LanguageEnglish
Published New York, USA Cambridge University Press 20.02.2024
Subjects
Acetochlor
active sites
acyl coenzyme A
Amaranth
Amaranthus palmeri
Amaranthus tuberculatus
Avena sativa
barley
benzofurans
biochemical pathways
Biosynthesis
Cell division
Cereal crops
Chemical industry
Chemical research
Corn
Crop production
Crops
Endoplasmic reticulum
epoxy compounds
family
fatty acid elongase
Fatty acids
Glycine max
Grasses
Group 15 herbicides
herbicide resistance
Herbicides
Hordeum vulgare
Inhibitors
isoxazolines
Leaves
Lewis bases
Metolachlor
oats
Pesticides
Plant growth
pyroxasulfone
Reclassification
residual herbicides
resistant weeds
Saccharum officinarum
shoot and root tissue
Sorghum
Sorghum bicolor
Soybeans
species
Substrates
Sugarcane
Sulfur
taxonomic revisions
technology
Thiocarbamates
Triticum aestivum
vegetables
very long chain fatty acids
Weed control
weed management
Weeds
wheat
Zea mays
α-chloroacetamides
United States > US
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Abstract 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 reclassification 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 to both corn and soybean crops in the United States with acetochlor and S-metolachlor being the most used VLCFA-inhibiting herbicides in corn and soybean production, respectively. The site of action of Group 15 herbicides results from inhibition of the VLCFA synthase, which is 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 its 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 to be resistant to VLCFA inhibitors, 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 of herbicide premixes and a valuable component of them. Nomenclature: Acetochlor; α-chloroacetamides; α-oxyacetamides; α-thioacetamides; azolyl-carboxamides; benzofurans; fenoxasulfone; isoxazolines; thiocarbamates; oxiranes; S-metolachlor; pyroxasulfone; Palmer amaranth, Amaranthus palmeri S. Watson; waterhemp, Amaranthus tuberculatus (Moq) J.D. Sauer; barley, Hordeum vulgare L.; corn, Zea mays L.; oat, Avena sativa L.; sorghum, Sorghum bicolor (L.) Moench; soybean, Glycine max L.; sugarcane, Saccharum officinarum L.; wheat, Triticum aestivum L.
AbstractList 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 reclassification 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 to both corn and soybean crops in the United States with acetochlor and S -metolachlor being the most used VLCFA-inhibiting herbicides in corn and soybean production, respectively. The site of action of Group 15 herbicides results from inhibition of the VLCFA synthase, which is 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 its 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 to be resistant to VLCFA inhibitors, 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 of herbicide premixes and a valuable component of them.
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 reclassification 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 to both corn and soybean crops in the United States with acetochlor and S-metolachlor being the most used VLCFA-inhibiting herbicides in corn and soybean production, respectively. The site of action of Group 15 herbicides results from inhibition of the VLCFA synthase, which is 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 its 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 to be resistant to VLCFA inhibitors, 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 of herbicide premixes and a valuable component of them. Nomenclature: Acetochlor; α-chloroacetamides; α-oxyacetamides; α-thioacetamides; azolyl-carboxamides; benzofurans; fenoxasulfone; isoxazolines; thiocarbamates; oxiranes; S-metolachlor; pyroxasulfone; Palmer amaranth, Amaranthus palmeri S. Watson; waterhemp, Amaranthus tuberculatus (Moq) J.D. Sauer; barley, Hordeum vulgare L.; corn, Zea mays L.; oat, Avena sativa L.; sorghum, Sorghum bicolor (L.) Moench; soybean, Glycine max L.; sugarcane, Saccharum officinarum L.; wheat, Triticum aestivum L.
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 reclassification 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 to both corn and soybean crops in the United States with acetochlor and S-metolachlor being the most used VLCFA-inhibiting herbicides in corn and soybean production, respectively. The site of action of Group 15 herbicides results from inhibition of the VLCFA synthase, which is 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 its 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 to be resistant to VLCFA inhibitors, 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 of herbicide premixes and a valuable component of them.
ArticleNumber e1
Author Singh, Rishabh
Ganie, Zahoor A.
Norsworthy, Jason K.
Jhala, Amit J.
Selby, Thomas P.
Shergill, Lovreet
Riechers, Dean E.
Singh, Mandeep
Jugulam, Mithila
Werle, Rodrigo
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  givenname: Amit J.
  orcidid: 0000-0001-8599-4996
  surname: Jhala
  fullname: Jhala, Amit J.
  organization: Professor & Associate Department Head, Department of Agronomy and Horticulture, University of Nebraska–Lincoln, Lincoln, NE, USA
– sequence: 2
  givenname: Mandeep
  surname: Singh
  fullname: Singh, Mandeep
  organization: Graduate Research Assistant, Department of Agronomy and Horticulture, University of Nebraska–Lincoln, Lincoln, NE, USA
– sequence: 3
  givenname: Lovreet
  surname: Shergill
  fullname: Shergill, Lovreet
  organization: Assistant Professor, Southern Ag Research Center, Montana State University, Huntley, MT, USA
– sequence: 4
  givenname: Rishabh
  surname: Singh
  fullname: Singh, Rishabh
  organization: Graduate Research Assistant, Department of Agronomy, Kansas State University, Manhattan, KS, USA
– sequence: 5
  givenname: Mithila
  surname: Jugulam
  fullname: Jugulam, Mithila
  organization: Professor, Department of Agronomy, Kansas State University, Manhattan, KS, USA
– sequence: 6
  givenname: Dean E.
  orcidid: 0000-0002-6081-5629
  surname: Riechers
  fullname: Riechers, Dean E.
  organization: Professor, Department of Crop Sciences, University of Illinois at Urbana–Champaign, Urbana, IL, USA
– sequence: 7
  givenname: Zahoor A.
  surname: Ganie
  fullname: Ganie, Zahoor A.
  organization: Senior Global R & D Scientist, Stine Research Center, FMC, Newark, DE
– sequence: 8
  givenname: Thomas P.
  surname: Selby
  fullname: Selby, Thomas P.
  organization: FMC Fellow, Global Research and Development Chemistry, Stine Research Center, FMC, Newark, DE
– sequence: 9
  givenname: Rodrigo
  orcidid: 0000-0003-1132-461X
  surname: Werle
  fullname: Werle, Rodrigo
  organization: Associate Professor, Department of Agronomy, University of Wisconsin–Madison, Madison, WI, USA
– sequence: 10
  givenname: Jason K.
  surname: Norsworthy
  fullname: Norsworthy, Jason K.
  organization: Distinguished Professor and Elms Farming Chair of Weed Science, Department of Crop, Soil, and Environmental Sciences, University of Arkansas, Fayetteville, AR, USA
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crossref_primary_10_3390_agriculture14081378
crossref_primary_10_1002_agg2_70074
crossref_primary_10_1002_ps_8458
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Copyright The Author(s), 2023. Published by Cambridge University Press on behalf of Weed Science Society of America. This work is licensed under the Creative Commons Attribution License This is an Open Access article, distributed under the terms of the Creative Commons Attribution licence (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted re-use, distribution and reproduction, provided the original article is properly cited. (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
Copyright_xml – notice: The Author(s), 2023. Published by Cambridge University Press on behalf of Weed Science Society of America. This work is licensed under the Creative Commons Attribution License This is an Open Access article, distributed under the terms of the Creative Commons Attribution licence (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted re-use, distribution and reproduction, provided the original article is properly cited. (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
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Thu Apr 24 22:54:45 EDT 2025
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PublicationTitle Weed technology
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Snippet The herbicides that inhibit very-long-chain fatty acid (VLCFA) elongases are primarily used for residual weed control in corn, barley, oat, sorghum, soybean,...
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SubjectTerms Acetochlor
active sites
acyl coenzyme A
Amaranth
Amaranthus palmeri
Amaranthus tuberculatus
Avena sativa
barley
benzofurans
biochemical pathways
Biosynthesis
Cell division
Cereal crops
Chemical industry
Chemical research
Corn
Crop production
Crops
Endoplasmic reticulum
epoxy compounds
family
fatty acid elongase
Fatty acids
Glycine max
Grasses
Group 15 herbicides
herbicide resistance
Herbicides
Hordeum vulgare
Inhibitors
isoxazolines
Leaves
Lewis bases
Metolachlor
oats
Pesticides
Plant growth
pyroxasulfone
Reclassification
residual herbicides
resistant weeds
Saccharum officinarum
shoot and root tissue
Sorghum
Sorghum bicolor
Soybeans
species
Substrates
Sugarcane
Sulfur
taxonomic revisions
technology
Thiocarbamates
Triticum aestivum
vegetables
very long chain fatty acids
Weed control
weed management
Weeds
wheat
Zea mays
α-chloroacetamides
Title Very long chain fatty acid–inhibiting herbicides: Current uses, site of action, herbicide-resistant weeds, and future
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