Skip to main content
SpringerLink
Log in

Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops

  • Review Article
  • Published:
Amino Acids Aims and scope Submit manuscript

Summary.

Acetohydroxyacid synthase (AHAS) inhibitors interfere with branched-chain amino acid biosynthesis by inhibiting AHAS. Glyphosate affects aromatic amino acid biosynthesis by inhibiting 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Glufosinate inhibits glutamine synthetase and blocks biosynthesis of glutamine. AHAS gene variants that confer tolerance to AHAS inhibitors have been discovered in plants through selection or mutagenesis. Imidazolinone-tolerant crops have been commercialized based on these AHAS gene variants. A modified maize EPSPS gene and CP4-EPSPS gene from Agrobacterium sp. have been used to transform plants for target-based tolerance to glyphosate. A gox gene isolated from Ochrobactrum anthropi has also been employed to encode glyphosate oxidoreductase to detoxify glyphosate in plants. Glyphosate-tolerant crops with EPSPS transgene alone or both EPSPS and gox transgenes have been commercialized. Similarly, bar and pat genes isolated from Streptomyces hygroscopicus and S. viridochromogenes, respectively, have been inserted into plants to encode phosphinothricin N-acetyltransferase to detoxify glufosinate. Glufosinate-tolerant crops have been commercialized using one of these two transgenes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

AHAS:

acetohydroxyacid synthase

AMPA:

aminomethylphosphonic acid

EPSP:

5-enolpyruvylshikimate-3-phosphate

EPSPS:

5-enolpyruvylshikimate-3-phosphate synthase

GOX:

glyphosate oxidoreductase

GS:

glutamine synthetase

PAT:

phosphinothricin N-acetyltransferase

References

  • AgBios (2005) GM crop database. http://www.agbios.com/dbase.php?action=ShowForm (accessed in March 2005)

  • Australian Office of the Gene Technology Regulator (2005) GM products approved as food, food additives and processing aids. http://www.ogtr.gov.au/gmorec/gmprod.htm (accessed in March 2005)

  • Barry G, Kishore G, Padgette S, Taylor M, Kolacz K, Weldon M, Re D, Eichholtz D, Fincher K, Hallas L (1992) Inhibitors of amino acid biosynthesis: strategies for imparting glyphosate tolerance to crop plants. In: Singh BK, Flores HE, Shannon JC (eds) Biosynthesis and molecular regulation of amino acids in plants. American Society of Plant Physiologists, Rockville, Md, pp 139–145

  • HJ Beckie G Seguin-Swartz H Nair SI Warwick E Johnson (2004) ArticleTitleMultiple herbicide-resistant canola can be controlled by alternative herbicides. Weed Sci 52 152–157 Occurrence Handle1:CAS:528:DC%2BD2cXlvVGrug%3D%3D

    CAS  Google Scholar 

  • Bender DA (1985) Amino acid metabolism, 2nd ed. John Wiley & Sons, Chichester

  • Berry K, Lutman PJW, Lotz LAP, Kempenaar C (2004) Genetically-modified herbicide-tolerant crops: a European perspective with a United Kingdom emphasis. In: Koul O, Dhaliwal GS (eds) Transgenic crop protection: concepts and strategies. Science Publishers, Inc., Enfield, New Hampshire, pp 117–156

  • Biotechnology Industry Organization (2004) Agricultural biotechnology products made available for sale as of February 5, 2004. http://www.bio.org/foodag/agbiotechprod.asp (accessed in March 2005)

  • Bright SWJ (1992) Herbicide-resistant crops. In: Singh BK, Flores HE, Shannon JC (eds) Biosynthesis and molecular regulation of amino acids in plants. American Society of Plant Physiologists, Rockville, Md, pp 184–194

  • Canadian Food Inspection Agency (2005) Status of regulated plants with novel traits in Canada: unconfined environmental release, novel livestock feed use, variety registration and novel food use. http://www.inspection.gc.ca/english/plaveg/bio/pntvcne.shtml (accessed in March 2005)

  • Chandler SF (1995) The use of herbicide resistance genes as selectable markers for producing transformed plants. In: McLean GD, Evans G (eds) Herbicide-resistant crops and pastures in Australian farming systems. Bureau of Resource Sciences, Parkes, ACT, Australia, pp 229–239

  • Christoffers MJ, Nandula VK, Mengistu LW, Messersmith CG (2004) Altered herbicide target sites: implications for herbicide-resistant weed management. In: Inderjit (ed) Weed biology and management. Kluwer Academic, Dordrecht, pp 199–210

  • Cole DJ (1985) Mode of action of glyphosate – a literature analysis. In: Grossbard E, Atkinson D (eds) The herbicide glyphosate. Butterworths, London, pp 48–74

  • D Cole K Pallett M Rodgers (2000) ArticleTitleDiscovering new modes of action for herbicides and the impact of genomics. Pestic Outlook 11 223–229 Occurrence Handle1:CAS:528:DC%2BD3MXotlaqsw%3D%3D

    CAS  Google Scholar 

  • Coupland D (1985) Metabolism of glyphosate in plants. In: Grossbard E, Atkinson D (eds) The herbicide glyphosate. Butterworths, London, pp 25–34

  • DeFelice MS (1998) Herbicide registration dates, use rates and acute toxicity by decade. In: Hatzios KK (ed) Herbicide handbook supplement to seventh edition. Weed Science Society of America, Lawrence, Kans, pp 81–86

  • J Dekker SO Duke (1995) ArticleTitleHerbicide-resistant field crops. Adv Agron 54 69–116 Occurrence Handle1:CAS:528:DyaK2MXlvFCrsb4%3D

    CAS  Google Scholar 

  • K D’Halluin M De Block J Janssens J Leemans A Reynaerts J Botterman (1992) ArticleTitleThe BAR gene as a selectable marker in plant engineering. Methods Enzymol 216 415–426 Occurrence Handle1:CAS:528:DyaK3sXkt1Whu7c%3D Occurrence Handle1479912

    CAS  PubMed  Google Scholar 

  • GM Dill (2005) ArticleTitleGlyphosate-resistant crops: history, status and future. Pest Manage Sci 61 219–224 Occurrence Handle10.1002/ps.1008 Occurrence Handle1:CAS:528:DC%2BD2MXitFOgurw%3D

    Article  CAS  Google Scholar 

  • W Droge I Broer A Pulher (1992) ArticleTitleTransgenic plants containing the phosphinothricin-N-acetyltransferase gene metabolize the herbicide L-phosphinothricin (glufosinate) differently from untransformed plants. Planta 187 142–151

    Google Scholar 

  • SO Duke (1990) ArticleTitleOverview of herbicide mechanisms of action. Environ Health Perspect 87 263–271 Occurrence Handle1:CAS:528:DyaK3cXmtVKmtbw%3D Occurrence Handle1980104

    CAS  PubMed  Google Scholar 

  • SO Duke (2005) ArticleTitleTaking stock of herbicide-resistant crops ten years after introduction. Pest Manage Sci 61 211–218 Occurrence Handle10.1002/ps.1024 Occurrence Handle1:CAS:528:DC%2BD2MXitFOgur8%3D

    Article  CAS  Google Scholar 

  • Duke SO, Scheffler BE, Dayan FE, Dyer WE (2002) Chapter 6, Genetic engineering crops for improved weed management traits. In: Rajasekaran K, Jacks TJ, Finley JW (eds) Crop biotechnology. ACS Symp Ser 829, American Chem Soc., Washington, DC, pp 52–66

  • Fabie A, Miller JF (2002) Cross resistance of two sulfonylurea-resistant sunflower sources to selected ALS herbicides. In: Proceedings of 24th Sunflower Research Workshop, pp 117–122

  • FDA (2005) List of completed consultations on bioengineered foods. http://vm.cfsan.fda.gov/~lrd/biocon.html (accessed in March 2005)

  • Franz JE, Mao MK, Sikorski JA (1997) Glyphosate: A unique global herbicide. ACS Monograph 189, American Chem Soc., Washington, DC

  • DR Gealy DH Mitten JN Rutger (2003) ArticleTitleGene flow between red rice (Oryza sativa) and herbicide-resistant rice (O. sativa): implications for weed management. Weed Technol 17 627–645

    Google Scholar 

  • Goodwin JL, Pastori GM, Davey MR, Jones HD (2005) Selectable markers: antibiotic and herbicide resistance. In: Pena L (ed) Transgenic plants: methods and protocols. Humana Press, Totowa, NJ, pp 191–202

  • Gressel J (2002a) Molecular biology of weed control. Taylor & Francis, London

  • Gressel J (2002b) Transgenic herbicide-resistant crops-advantages, drawbacks, and failsafes. In: Oksman-Caldentey K, Barz WH (eds) Plant biotechnology and transgenic plants. Marcel Dekker, New York, pp 597–633

  • Health Canada (2005) Novel food decisions. http://www.hc-sc.gc.ca/food-aliment/mh-dm/ofb-bba/nfi-ani/e_nf_dec.html (accessed in March 2005)

  • Herbicide Resistance Action Committee (2005) Classification of herbicides according to mode of action. http://www.plantprotection.org/HRAC/ (accessed in March 2005)

  • FD Hess (2000) ArticleTitleLight-dependent herbicides: an overview. Weed Sci 48 160–170 Occurrence Handle1:CAS:528:DC%2BD3cXjsFeqsrg%3D

    CAS  Google Scholar 

  • Kirkwood RC (2002) Herbicide-tolerant crops. In: Naylor REL (ed) Weed management handbook. Blackwell, Oxford, pp 253–279

  • G Kishore D Shah (1988) ArticleTitleAmino acid biosynthesis inhibitors as herbicides. Annu Rev Biochem 57 627–663 Occurrence Handle10.1146/annurev.bi.57.070188.003211 Occurrence Handle1:CAS:528:DyaL1cXkvVyjsLs%3D Occurrence Handle3052285

    Article  CAS  PubMed  Google Scholar 

  • D Komoba I Gennity H Sandermann SuffixJr (1992) ArticleTitlePlant metabolism of herbicides with C–P bonds: glyphosate. Pesticide Biochem Physiol 43 85–94

    Google Scholar 

  • D Komoba H Sandermann SuffixJr (1992) ArticleTitlePlant metabolism of herbicides with C–P bonds: phosphinothricin. Pesticide Biochem Physiol 43 95–102

    Google Scholar 

  • RA LaRossa SC Falco (1984) ArticleTitleAmino acid biosynthetic enzymes as targets of herbicide action. Trends Biotechnol 2 158–161 Occurrence Handle10.1016/0167-7799(84)90033-7 Occurrence Handle1:CAS:528:DyaL2MXntl2ksw%3D%3D

    Article  CAS  Google Scholar 

  • Lebrun M, Sailland A, Freyssinet G, Degryse E (2003) Mutated 5-enolpyruvylshikimate-3-phosphate synthase, gene coding for said protein and transformed plants containing said gene, US patent 6 566 587, http://www.uspto.gov/patft/index.html (accessed in March 2005)

  • CA Mallory-Smith EJ Retzinger SuffixJr (2003) ArticleTitleRevised classification of herbicides by site of action for weed resistance management strategies. Weed Technol 17 605–619 Occurrence Handle1:CAS:528:DC%2BD3sXotF2qu78%3D

    CAS  Google Scholar 

  • M Matringe A Sailland B Pelissier A Rolland O Zink (2005) ArticleTitlep-Hydroxyphenylpyruvate dioxygenase inhibitor-resistant plants. Pest Manage Sci 61 269–276 Occurrence Handle10.1002/ps.997 Occurrence Handle1:CAS:528:DC%2BD2MXitFOgurY%3D

    Article  CAS  Google Scholar 

  • Mousdale DM, Coggins JR (1991) Amino acid synthesis. In: Kirkwood RC (ed) Target sites for herbicide action. Plenum Press, New York, pp 29–56

  • BP Muller A Zumdick I Schuphan B Schmidt (2001) ArticleTitleMetabolism of the herbicide Glufosinate ammonium in plant cell cultures of transgenic (rhizomania-resistant) and non-transgenic sugarbeet (Beta vulgaris), carrot (Daucus carota), purple foxglove (Digitalis purpurea) and thorn apple (Datura stramonium). Pest Manage Sci 57 46–56 Occurrence Handle1:CAS:528:DC%2BD3MXotFWqtg%3D%3D

    CAS  Google Scholar 

  • Newhouse K, Wang T, Anderson P (1991) Imidazolinone-tolerant crops. In: Shaner DL, O’Conner SL (eds) The imidazolinone herbicides. CRC Press, Boca Raton, Fla, pp 139–150

  • OECD (1999) Consensus document on general information concerning the genes and their enzymes that confer tolerance to glyphosate herbicide. Series on harmonization of regulatory oversight in biotechnology No. 10, http://www.olis.oecd.org/olis/1999doc.nsf/LinkTo/env-jm-mono(99)9 (accessed in March 2005)

  • OECD (2002) Module II: herbicide biochemistry, herbicide metabolism and the residues in glufosinate-ammonium (phosphinothricin)-tolerant transgenic plants. Series on harmonization of regulatory oversight in biotechnology No. 25 http://www.olis.oecd.org/olis/2002doc.nsf/LinkTo/env-jm-mono(2002)14 (accessed in March 2005)

  • K Ott J Kwagh GW Stockton V Sidorov G Kakefuda (1996) ArticleTitleRational molecular design and genetic engineering of herbicide resistant crops by structure modeling and site-directed mutagenesis of acetohydroxyacid synthase. J Mol Biol 263 359–368 Occurrence Handle10.1006/jmbi.1996.0580 Occurrence Handle1:CAS:528:DyaK28Xms1Wluro%3D Occurrence Handle8913312

    Article  CAS  PubMed  Google Scholar 

  • Padgette SR, Re DB, Barry GF, Eichholtz DE, Delannay X, Fuchs RL, Kishore GM, Fraley RT (1996) New weed control opportunities: development of soybeans with a Roundup Ready™ gene. In: Duke SO (ed) Herbicide resistant crops. CRC Press, Boca Raton, Fla, pp 53–84

  • SS Pang LW Guddat RG Duggleby (2003) ArticleTitleMolecular basis of sulfonylurea herbicide inhibition of acetohydroxyacid synthase. J Biol Chem 278 7639–7644 Occurrence Handle1:CAS:528:DC%2BD3sXhsVKiuro%3D Occurrence Handle12496246

    CAS  PubMed  Google Scholar 

  • W Pline-Srnic (2005) ArticleTitleTechnical performance of some commercial glyphosate-resistant crops. Pest Manage Sci 61 225–234 Occurrence Handle10.1002/ps.1009 Occurrence Handle1:CAS:528:DC%2BD2MXitFOgur0%3D

    Article  CAS  Google Scholar 

  • Rasche E (1995) Development of glufosinate ammonium tolerant crops and the selective use of the herbicide glufosinate ammonium. In: McLean GD, Evans G (eds) Herbicide-resistant crops and pastures in Australian farming systems. Bureau of Resource Sciences, Parkes, ACT, Australia, pp 25–33

  • K Ray A Jagannath SA Gangwani PK Burma D Pental (2004) ArticleTitleMutant acetolactate synthase gene is an efficient in vitro selectable marker for the genetic transformation of Brassica juncea (oilseed mustard). J Plant Physiol 161 1079–1083 Occurrence Handle10.1016/j.jplph.2004.02.001 Occurrence Handle1:CAS:528:DC%2BD2cXptlOgt7s%3D Occurrence Handle15499910

    Article  CAS  PubMed  Google Scholar 

  • Reade JPH, Cobb AH (2002) Herbicides: modes of action and metabolism. In: Naylor REL (ed) Weed management handbook. Blackwell Science, Oxford, pp 134–170

  • KN Reddy AM Rimando SO Duke (2004) ArticleTitleAminomethylphosphonic acid, a metabolite of glyphosate, causes injury in glyphosate-treated, glyphosate-resistant soybean. J Agric Food Chem 52 5139–5143 Occurrence Handle1:CAS:528:DC%2BD2cXlsFahtLg%3D Occurrence Handle15291487

    CAS  PubMed  Google Scholar 

  • M Ruhland G Engelhardt K Pawlizki (2004) ArticleTitleDistribution and metabolism of D/L-, L- and D-glufosinate in transgenic, glufosinate tolerant crops of maize (Zea mays L ssp mays) and oilseed rape (Brassica napus L. var napus). Pest Manage Sci 60 691–696 Occurrence Handle10.1002/ps.857 Occurrence Handle1:CAS:528:DC%2BD2cXlslaisLs%3D

    Article  CAS  Google Scholar 

  • Saari LL, Mauvais CJ (1996) Chapter 8, Sulfonylurea herbicide-resistant crops. In: Duke SO (ed) Herbicide resistant crops. CRC Press, Boca Raton, Fla, pp 127–142

  • SA Sebastian GM Fader JF Ulrich DR Forney RS Chaleff (1989) ArticleTitleSemidominant soybean mutation for resistance to sulfonylurea herbicides. Crop Sci 29 1403–1408 Occurrence Handle1:CAS:528:DyaK3cXjtlCluw%3D%3D

    CAS  Google Scholar 

  • Shaner DL, Bascomb NF, Smith W (1996) Chapter 9, Imidazolinone-resistant crops: selection, characterization, and management. In: Duke SO (ed) Herbicide resistant crops. CRC Press, Boca Raton, Fla, pp 143–157

  • Shaner DL, Singh BK (1992) How does inhibition of amino acid biosynthesis kill plants? In: Singh BK, Flores HE, Shannon JC (eds) Biosynthesis and molecular regulation of amino acids in plants. American Society of Plant Physiologists, Rockville, Md, pp 174–183

  • Shaner DL, Singh BK (1997) Acetohydroxyacid synthase inhibitors. In: Roe RM (ed) Herbicide activity: toxicology, biochemistry and molecular biology. IOS Press, Washington, DC, pp 69–110

  • Sherman TD, Vaughn KC, Duke SO (1996) Mechanisms of action and resistance to herbicides. In: Duke SO (ed) Herbicide resistant crops. CRC Press, Boca Raton, Fla, pp 13–35

  • MJ Simard A Legere D Pageau J Lajeunesse S Warwick (2002) ArticleTitleThe frequency and persistence of volunteer canola (Brassica napus) in Quebec cropping systems. Weed Technol 16 433–439

    Google Scholar 

  • BK Singh DL Shaner (1995) ArticleTitleBiosynthesis of branched chain amino acids: from test tube to field. Plant Cell 7 935–944 Occurrence Handle10.1105/tpc.7.7.935 Occurrence Handle1:CAS:528:DyaK2MXnt1Sgtrg%3D Occurrence Handle12242394

    Article  CAS  PubMed  Google Scholar 

  • Stidham MA, Singh BK (1991) Imidazolinone-acetohydroxyacid synthase interactions. In: Shaner DL, O’Conner SL (eds) The imidazolinone herbicides. CRC Press, Boca Raton, Fla, pp 71–90

  • S Tan RR Evans ML Dahmer BK Singh DL Shaner (2005) ArticleTitleImidazolinone-tolerant crops: history, current status and future. Pest Manage Sci 61 246–257 Occurrence Handle10.1002/ps.993 Occurrence Handle1:CAS:528:DC%2BD2MXitFOgurg%3D

    Article  CAS  Google Scholar 

  • PJ Tranel TR Wright (2002) ArticleTitleResistance of weeds to ALS-inhibiting herbicides: what have we learned? Weed Sci 50 700–712 Occurrence Handle1:CAS:528:DC%2BD38XptV2jtL4%3D

    CAS  Google Scholar 

  • Tranel PJ, Wright TR, Heep IM (2005) ALS mutations from herbicide-resistant weeds. http://www.weedscience.com (accessed in March 2005)

  • USDA (2005a) The U.S. database of completed regulatory agency reviews. http://usbiotechreg.nbii.gov/database_pub.asp (accessed in March 2005)

  • USDA (2005b) Field test releases in the U.S. http://www.isb.vt.edu/cfdocs/fieldtests1.cfm (accessed in March 2005)

  • Vasil IK (1996) Phosphinothricin-resistant crops. In: Duke SO (ed) Herbicide resistant crops. CRC Press, Boca Raton, Fla, pp 85–91

  • KC Vaughn SO Duke (1991) ArticleTitleBiochemical basis of herbicide resistance. Chem Plant Protect 7 141–169 Occurrence Handle1:CAS:528:DyaK38Xhs1yhtrc%3D

    CAS  Google Scholar 

  • Vencill WK (ed) (2002) Herbicide handbook. Weed Science Society of America, Lawrence, Kans

  • K Wakabayashi P Boger (2002) ArticleTitleTarget sites for herbicides: entering the 21st century. Pest Manage Sci 58 1149–1154 Occurrence Handle10.1002/ps.560 Occurrence Handle1:CAS:528:DC%2BD38XosFyrtLg%3D

    Article  CAS  Google Scholar 

  • LS Watrud EH Lee A Fairbrother C Burdick JR Reichman M Bollman M Storm G King PK Van de Water (2004) ArticleTitleEvidence for landscape-level, pollen-mediated gene flow from genetically modified creeping bentgrass with CP4 EPSPS as a marker. Proc Natl Acad Sci USA 101 14533–14538 Occurrence Handle10.1073/pnas.0405154101 Occurrence Handle1:CAS:528:DC%2BD2cXovVeru7o%3D Occurrence Handle15448206

    Article  CAS  PubMed  Google Scholar 

  • A Wehrmann A Van Vliet C Opsomer J Botterman A Schulz (1996) ArticleTitleThe similarities of bar and pat gene products make them equally applicable for plant engineers. Nat Biotechnol 14 1274–1278 Occurrence Handle10.1038/nbt1096-1274 Occurrence Handle1:CAS:528:DyaK28XmtFagsrg%3D Occurrence Handle9631092

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. BASF Corporation, Research Triangle Park, North Carolina, U.S.A.

    S. Tan, R. Evans & B. Singh

Authors
  1. S. Tan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Evans
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tan, S., Evans, R. & Singh, B. Herbicidal inhibitors of amino acid biosynthesis and herbicide-tolerant crops. Amino Acids 30, 195–204 (2006). https://doi.org/10.1007/s00726-005-0254-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00726-005-0254-1

Search

Navigation