Hostname: page-component-cd9895bd7-mkpzs Total loading time: 0 Render date: 2024-12-26T03:37:33.147Z Has data issue: false hasContentIssue false
  • English
  • Français

Quinclorac belongs to a new class of highly selective auxin herbicides

Published online by Cambridge University Press:  12 June 2017

Klaus Grossmann
Klaus Grossmann*
Affiliation:
BASF Agricultural Center Limburgerhof, D-67114 Limburgerhof, Germany; Klaus.grossmann@msm.basf-ag.de
Get access Rights & Permissions [Opens in a new window]

Abstract

Substituted quinolinecarboxylic acids, including quinclorac (BAS 514H), are a new class of highly selective auxin herbicides, which are chemically similar to naturally occurring compounds isolated from plants and soils. Quinclorac is used in rice to control important dicot and monocot weeds, particularly barnyardgrass. The herbicide has also been developed for application in turfgrass areas, spring wheat, and chemical fallow. Quinclorac is readily absorbed by germinating seeds, roots, and leaves and is translocated in the plant both acropetally and basipetally. By mimicking an auxin overdose, quinclorac affects the phytohormonal system in sensitive plants. The compound stimulates the induction of 1-aminocyclopropane-1-carboxylic acid (ACC) synthase activity and thus promotes ethylene biosynthesis. In susceptible dicots, increased levels of ethylene trigger an accumulation of abscisic acid (ABA), which, as part of the intrinsic auxin activity of quinclorac, plays a major role in growth inhibition and the induction of epinasty and senescence. In sensitive grasses, such as barnyardgrass species, large crabgrass, broadleaf signalgrass, and green foxtail, quinclorac leads particularly to an accumulation of tissue cyanide, formed as a co-product during increased ACC and ethylene synthesis. This causes phytotoxicity characterized by the inhibition of root and particularly shoot growth with tissue chlorosis and subsequent necrosis. These effects were not observed in tolerant rice and a resistant biotype of barnyardgrass. No significant differences in uptake, translocation, or metabolism of quinclorac between resistant and sensitive grasses were found. Hence, a target-site-based mechanism of selectivity is suggested. The induction process of the ACC synthase activity plays the primary role in the selective herbicide action of quinclorac. This is a common effect of auxin herbicides and auxins, which lead to the accumulation of cyanide and/or ABA depending on the plant species and tissues, the compound concentration in the tissue, and their biological activity.

Keywords

Clopyralid2,4DdicambaIAA, indole-3-acetic acidMCPAα-NAA, α-naphthaleneacetic acidpicloramquinclorac, BAS 514H, 3,7-dichloro-8-quinolinecarboxylic acidquinmerac, 7-chloro-3-methyl-8-quinolinecarboxylic acidbroadleaf signalgrass, Brachiaria platyphylla (Griseb.) Nashbarnyardgrass, Echinochloa crus-galli (L.) P. Beauv. ECHCGlarge crabgrass, Digitaria sanguinalis (L.) Scop. DIGSAgreen foxtail, Setaria viridis (L.) P. Beauv. SETVIrice, Oryza sativa L. ORYSAspring wheat, Triticum aestivum L. TRZASAbscisic acidACC synthaseauxin herbicidescyanideethyleneECHCGDIGSASETVIORYSATRZAS
Type
Special Topics
Information
Weed Science , Volume 46 , Issue 6 , December 1998 , pp. 707 - 716
Copyright
Copyright © 1998 by the Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

Abel, S. and Theologis, A. 1996. Early genes and auxin action. Plant Physiol. 111: 9–17.Google Scholar
Abeles, F. B., Morgan, P. W., and Saltveit, M. E., eds. 1992. Ethylene in Plant Biology. San Diego, CA: Academic Press.Google Scholar
Beale, M. H. and Sponsel, V. M. 1993. Future directions in plant hormone research. J. Plant Growth Regul. 12: 227–235.Google Scholar
Beck, J. M., Ito, M., and Kashibuchi, S. 1989. Quinclorac (BAS 514H) and its herbicide combination in transplanted rice in Japan. Page 235 in Proceedings of the 12th Asian-Pacific Weed Science Society Conference.Google Scholar
Bennett, M. J., Marchant, A., Green, H. G., May, S. T., Ward, S. P., Millner, P. A., Walker, A. R., Schulz, B., and Feldmann, K. A. 1996. Arabidopsis AUX 1 gene: a permease-like regulator of root gravitropism. Science 273: 948–950.CrossRefGoogle Scholar
Berghaus, R. and Wuerzer, B. 1987. The mode of action of the new experimental herbicide, quinclorac (BAS 514H). Pages 81–87 in Proceedings of the 11th Asian-Pacific Weed Science Society Conference.Google Scholar
Berghaus, R. and Wuerzer, B. 1989. Uptake, translocation and metabolism of quinclorac (BAS 514H) in rice and barnyard grass. Pages 133–139 in Proceedings of the 12th Asian-Pacific Weed Science Society Conference.Google Scholar
Briggs, G. G., Rigitano, R.L.O., and Bromilow, R. H. 1987. Physico-chemical factors affecting uptake by roots and Translocation to shoots of weak acids in barley. Pestic. Sci. 19: 101–112.CrossRefGoogle Scholar
Chism, W. J., Bingham, S. W., and Shaver, R. L. 1991. Uptake, translocation, and metabolism of quinclorac in two grass species. Weed Technol. 5: 771–775.Google Scholar
Cleland, R. E. 1995. Auxin and cell elongation. Pages 214–217 in Davies, P. J., ed. Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht: Kluwer.CrossRefGoogle Scholar
Coupland, D. 1994. Resistance to the auxin analog herbicides. Pages 171–214 in Powles, S. B. and Holtum, J.A.M., eds. Herbicide Resistance in Plants. Biology and Biochemistry. Boca Raton, FL: Lewis.Google Scholar
Davies, P. J. 1995. Introduction. Pages 1–12 in Davies, P. J., ed. Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht: Kluwer.Google Scholar
Devine, M., Duke, S. O., and Fedtke, C., eds. 1993. Herbicides with auxin activity. Pages 295–309 in Physiology of Herbicide Action. Englewood Cliffs, NJ: Prentice Hall.Google Scholar
Estelle, M. 1992. The plant hormone auxin: insight in sight. BioEssays 14: 439–444.Google Scholar
Finlayson, S. A., Liu, J-H., and Reid, D. M. 1996. Localization of ethylene biosynthesis in roots of sunflower (Helianthus annuus) seedlings. Physiol. Plant. 96: 36–42.CrossRefGoogle Scholar
Franetovich, L. M. and Peeper, T. F. 1995. Quinclorac for cheat (Bromus secalinus) control in winter wheat (Triticum aestivum) . Weed Technol. 9:131–140.CrossRefGoogle Scholar
Gianfagna, T. J. 1995. Natural and synthetic growth regulators and their use in horticultural and agronomic crops. Pages 751–773 in Davies, P. J., ed. Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht: Kluwer.Google Scholar
Gilbert, F. A. 1946. The status of plant-growth substances and herbicides in 1945. Chem. Rev. 39: 199–218.CrossRefGoogle Scholar
Grossmann, K. 1996. A role for cyanide, derived from ethylene biosynthesis, in the development of stress symptoms. Physiol. Plant. 97: 772–775.CrossRefGoogle Scholar
Grossmann, K. 1997. Highly selective, auxin herbicides of the quinolinecarboxylic acid type. The mode of action of the rice herbicide quinclorac (Facet). Pages 45–53 in Pandalai, S. G., ed. Recent Research Developments in Plant Physiology 1. Trivandrum, India: Research Signpost.Google Scholar
Grossmann, K. and Kwiatkowski, J. 1993. Selective induction of ethylene and cyanide biosynthesis appears to be involved in the selectivity of the herbicide quinclorac between rice and barnyard grass. J. Plant Physiol. 142: 457–466.CrossRefGoogle Scholar
Grossmann, K. and Kwiatkowski, J. 1995. Evidence for a causative role of cyanide, derived from ethylene biosynthesis, in the herbicidal mode of action of quinclorac in barnyard grass. Pestic. Biochem. Physiol. 51: 150–160.Google Scholar
Grossmann, K. and Retzlaff, G. 1997. Bioregulatory effects of the fungicidal strobilurin kresoxim-methyl in wheat (Triticum aestivum) . Pestic. Sci. 50: 11–20.Google Scholar
Grossmann, K. and Scheltrup, F. 1995. On the mode of action of the new, selective herbicide quinmerac. Brighton Crop Prot. Conf. Weeds: 1: 393–398.Google Scholar
Grossmann, K. and Scheltrup, F. 1997. Selective induction of 1-aminocyclopropane-1-carboxylic acid (ACC) synthase activity is involved in the selectivity of the auxin herbicide quinclorac between barnyard grass and rice. Pestic. Biochem. Physiol. 58: 145–153.CrossRefGoogle Scholar
Grossmann, K. and Scheltrup, F. 1998. Studies on the mechanism of selectivity of the auxin herbicide quinmerac. Pestic. Sci. 52: 111–118.Google Scholar
Grossmann, K., Scheltrup, F., Kwiatkowski, J., and Caspar, G. 1996. Induction of abscisic acid is a common effect of auxin herbicides in susceptible plants. J. Plant Physiol. 149: 475–478.Google Scholar
Grossmann, K. and Schmülling, T. 1995. The effects of the herbicide quinclorac on shoot growth in tomato is alleviated by inhibitors of ethylene biosynthesis and by the presence of an antisense construct to the 1-aminocyclopropane-1-carboxylic acid (ACC) synthase gene in transgenic plants. Plant Growth Regul. 16: 183–188.Google Scholar
Hager, A., Debus, G., Edel, H-G., Stransky, H., and Serrano, R. 1991. Auxin induces exocytosis and the rapid synthesis of a high-turnover pool of plasma-membrane H+-ATPase. Planta 185: 527–537.CrossRefGoogle ScholarPubMed
Hayashi, T. and Maclachlan, G. 1984. Pea xyloglucan and cellulose. III. Metabolism during lateral expansion of pea epicotyl cells. Plant Physiol. 76: 739–742.Google Scholar
Kende, H. 1993. Ethylene biosynthesis. Annu. Rev. Plant Physiol. Plant Mol. Biol. 44: 283–307.Google Scholar
Kibler, E., Menck, B. H., and Rosebrock, H. 1987. Quinclorac—a new Echinochloa-herbicide for rice and an excellent partner for broad spectrum rice herbicides. Pages 89–97 in Proceedings of the 11th Asian-Pacific Weed Society Conference.Google Scholar
Klee, H. J. and Lanahan, M. B. 1995. Transgenic plants in hormone biology. Pages 340–353 in Davies, P. J., ed. Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht: Kluwer.Google Scholar
Koo, S. J., Kwon, Y. W., and Cho, K. Y. 1991. Differences in selectivity and physiological effects of quinclorac between rice and barnyard grass compared with 2,4-D. Pages 103–111 in Proceedings of the 13th Asian-Pacific Weed Society Conference.Google Scholar
Koo, S. J., Neal, J. C., and DiTomaso, J. M. 1996. 3,7-Dichloroquinolinecarboxylic acid inhibits cell-wall biosynthesis in maize roots. Plant Physiol. 112: 1383–1389.CrossRefGoogle ScholarPubMed
Koo, S. J., Neal, J. C., and DiTomaso, J. M. 1997. Mechanism of action and selectivity of quinclorac in grass roots. Pestic. Biochem. Physiol. 57: 44–53.Google Scholar
Lamoureux, G. L. and Rusness, D. G. 1995. Quinclorac absorption, translocation, metabolism, and toxicity in leafy spurge (Euphorbia esula) . Pestic. Biochem. Physiol. 53: 210–226.Google Scholar
Lopez-Martinez, N. and De Prado, R. 1996. Fate of quinclorac in resistant Echinochloa crus-galli . Pages 535–540 in Second International Weed Control Congress, Copenhagen.Google Scholar
Lopez-Martinez, N., Marshall, G., and De Prado, R. 1997. Resistance of barnyard grass (Echinochloa crus-galli) to atrazine and quinclorac. Pestic. Sci. 51: 171–175.3.0.CO;2-7>CrossRefGoogle Scholar
Macdonald, H. 1997. Auxin perception and signal transduction. Physiol. Plant. 100: 423–439.Google Scholar
Matsushima, H., Fakumi, H., and Arima, K. 1973. Isolation of zeanic acid, a natural plant growth regulator from corn steep liquor and its chemical structure. Agric. Biol. Chem. 37: 1865–1871.Google Scholar
McKeon, T. A., Fernandez-Maculet, J. C., and Yang, S. F. 1995. Biosynthesis and metabolism of ethylene. Pages 118–139 in Davies, P. J., ed. Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht: Kluwer.Google Scholar
Miro, N. and Bennett, A. B. 1995. The diageotropica mutation and synthetic auxins differentially affect the expression of auxin-regulated genes in tomato. Plant Physiol. 109: 293–297.Google Scholar
Mito, N., Sori, I., Miyakado, M., and Tanaka, S. 1991. Competition by auxin-type herbicides for NAA binding to maize auxin binding protein: comparison with in vivo auxin activity. J. Pestic. Sci. 16: 435–439.CrossRefGoogle Scholar
Mito, N., Yoshida, R., and Oshio, H. 1990. Effects of hormone-type herbicides on proton excretion and anthocyanin synthesis of mung bean hypocotyl sections. Weed Res. Jpn. 35: 332–339.Google Scholar
Morgan, P. W. 1976. Effect of ethylene physiology. Pages 256–280 in Audus, L. J., ed. Herbicides: Physiology, Biochemistry, and Ecology. New York: Academic Press.Google Scholar
Neal, J. C. 1990. Non-phenoxy herbicides for perennial broadleaf weed control in cool-season turf. Weed Technol. 4: 555–559.Google Scholar
Pallett, K. E. 1991. Other primary target sites of herbicides. Pages 124–167 in Kirkwood, R. C., ed. Target Sites for Herbicide Action. New York: Plenum Press.Google Scholar
Rademacher, W. and Evans, J. R. 1996. Pix and other PGRs for crop plants. Proc. Plant Growth Regul. Soc. Am. 236–241.Google Scholar
Sahashi, Y. 1925. Über das Vorkommen von Di-Hydroxy-Chinolin-Carbonsäure in der Reiskleie. Biochem. Z. 159: 221–234.Google Scholar
Scheltrup, F. and Grossmann, K. 1995. Abscisic acid is a causative factor in the mode of action of the auxinic herbicide quinmerac in cleaver (Galium aparine L.). J. Plant Physiol. 147: 118–126.Google Scholar
Scherer, G. and Andre, B. 1993. Stimulation of phospholipase A2 by auxin microsomes from suspension-cultured soybean cells is receptor-mediated and influenced by nucleotides. Planta 191: 515–523.Google Scholar
Schott, P. E., Will, H., Schlüter, A., Meumann, H., Rademacher, W., and Schelberger, K. 1989. Influence of two auxin analogues on fruit set and quality of tomatoes. Acta Hortic. 239: 391–394.Google Scholar
Sitbon, F. and Perrot-Rechenmann, C. 1997. Expression of auxin-regulated genes. Physiol. Plant. 100: 443–455.Google Scholar
Starratt, A. N. and Caveney, S. 1996. Quinoline-2-carboxylic acids from Ephedra species. Phytochemistry 42: 1477–1478.Google Scholar
Sterling, T. M. and Hall, J. C. 1997. Mechanism of action of natural auxins and the auxinic herbicides. Pages 111–141 in Roe, R. M., Burton, J. D., and Kuhr, R. J., eds. Herbicide Activity: Toxicology, Biochemistry and Molecular Biology. Amsterdam: IOS Press.Google Scholar
Street, J. E. and Mueller, T. C. 1993. Rice (Oryza sativa) weed control with soil application of quinclorac. Weed Technol. 7: 600–604.Google Scholar
Sunohara, Y. and Matsumoto, H. 1997. Comparative physiological effects of quinclorac and auxins, and light involvement in quinclorac-induced chlorosis in corn leaves. Pestic. Biochem. Physiol. 58: 125–132.Google Scholar
Tittle, F. L., Goudey, J. S., and Spencer, M. S. 1990. Effects of 2,4-di-chlorophenoxyacetic acid on endogenous cyanide, β-cyanoalanine synthase activity, and ethylene evolution in seedlings of soybean and barley. Plant Physiol. 94: 1143–1148.Google Scholar
Walter, H., Retzlaff, G., Berghaus, R., and Landes, M. 1994. Einfluβfaktoren auf die Wirkung von Quinmerac und Quinmerac-haltigen Kombinationsprodukten. Z. Pflanzenkr. Pflanzenschurz, Sonderheft 14: 583–594.Google Scholar
Wang, Y., Deshpande, S., and Hall, J. C. 1997. Calcium ion dynamics in auxinic-herbicide resistant and susceptible biotypes of Sinapis arvensis . Brighton Crop Prot. Conf. Weeds 2: 765–770.Google Scholar
Wen, J-Q., Huang, F., Liang, W-S., and Liang, H-G. 1997. Increase of HCN and β-cyanoalanine synthase activity during ageing of potato tuber slices. Plant Sci. 125: 147–151.Google Scholar
Wuerzer, B., Berghaus, R., Hagen, H., Kohler, R-D., and Markert, J. 1985. Characteristics of the new herbicide BAS 518H. Br. Crop Prot. Conf. Weeds 1: 63–70.Google Scholar