2-Methylquinolin-4(1H)-on-3-acetic acids as Inhibitors of seed germination and early growth of seedlings

Paper Details

Research Paper 01/10/2016
Views (444) Download (28)
current_issue_feature_image
publication_file

2-Methylquinolin-4(1H)-on-3-acetic acids as Inhibitors of seed germination and early growth of seedlings

Fauzia Anjum Chattha, Munawar Ali Munawar, Samina Kousar
Int. J. Agron. Agri. Res.9( 4), 9-15, October 2016.
Certificate: IJAAR 2016 [Generate Certificate]

Abstract

Quinolines are important herbicides and are used widely but their acetic acids function is still detectable that might have some prominent effects on seed germination and growth of plantlets. A series of 2-methylquinolin-4(1H)-on-3-acetic acids have been synthesized from substituted anilines. These compounds were subjected to evaluate their biological action on wheat (Triticum aestivum) and sorghum (Sorghum bicolor) seeds germination along with early growth of seedlings. At high concentrations these compounds were proved to have inhibitory effect on root and shoot growth both in sorghum and wheat. While at low concentration these compounds were found to have stimulatory effect on sorghum but inhibitory effect on wheat growth. Quinolin-4(1H)-on-3-acetic acids is supposed to delay the germination of seeds simply by lowering the metabolic process during the imbibitions.

VIEWS 12

Arthur H. 1953. ‘Herbicides’ US Patent 2661276.

Avetisyan AA, Aleksanyana IL, Pivazyan AA. 2004. New quinoline derivatives on the basis of (4-hydroxy-2-methylquinolin-3-yl) acetic acid. Russian Journal of Organic Chemistry 40, 889-91.

Avron M. 1961. The inhibition of photoreactions of chloroplasts by 2-alkyl-4-hydroxyquinoline N-oxides. Biochemistry Journal 78, 735-739.

Berghaus R, Wuerzer B. 1987. The mode of action of the new herbicide quinclorac. In: the 11th Asian Pacific Weed Science Society Conference pp 81-87.

Berghaus R, Wuerzer B. 1989. Uptake, translocation and metabolism of quinclorac in rice and grass. In: the 12th Asian Pacific Weed Science Society Conference p 133.

Cavusoglu K, Kaba K. 2007. Comparison of antagonisms between abscisic acid and various growth stimulators during germination of barley and radish seeds. EurAsian Journal of BioScience 2, 11-21.

Chattha FA, Munawar AM, Ashraf M, Nagra SA, Nisa M-U, Fatima I. 2012. Synthesis of 2-methyl-4-quinolone-3-acetic acids with Potential antibacterial activity. Journal of Chillean Chemical Society 57, Nº 3, 1-3.

Chattha FA, Munawar MA, Ashraf M, Kousar S, Nagra SA. 2012. Synthesis of 3-aryl-1H-indazole derivatives and study of their plant growth regulating activity. J. Plant Growth Regulation 32(2), 291-297. DOI 10.1007/s00344-012-9297-1.

Goren R, Tomer E. 1971. Effect of seselin and coumarin on growth, indoleacetic aicd oxidase and peroxidase with special reference to cucumber radicles. Plant Physiology 47, 312-316.

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. Pesticide Biochemistry Physiology 51, 150-160.

Grossmann K. 1998. Quinclorac belongs to a new class of highly selective auxin herbicides. Weed Science 46, 707.

Grossmann K. 2010. Auxin herbicides: current status of mechanism and mode of action. Pest Management Science 66, 113-120.

Hagen HF, Market JM, Wuerzer BO. 1985. Dicholroquinoline derivatives for use as herbicides. US 449765.

Hubele A. 1994. Use of quinoline derivatives for the protection of cultivated plants. US Patent EP0094349B1.

Iwata T, Nakanishi K, Nagao M, Ishida S, Kamuro Y. 1977. Methods for thinning young fruits and blossoms and agent therefore. US 4008070.

Lamoureux GL, Rusness DG. 1995. Quinclorac absorption, translocation, metabolism, and toxicity in leafy spurge (Euphorbia esula). Pesticide Biochemistry and Physiology 53, 210-226.

Lightbown JW, Jackson FL. 1956. Inhibition of cytochrome systems of heart muscle and certain bacteria by the antagonists of dihydrostreptomycin: 2-alkyl-4-hydroxyquinoline N-oxide. Biochemistry Journal 63, 130-137.

Noggle GR, Fritz GJ. 1976. Introduction to plant Physiology. Princenton Hall, inc., Englewood Cliffs, New Jersey.

Plath PF, Eicken KW, Zeeh BL, Eichenauer UF, Kohler R-D, Meyer NL, Wuerzer BO. 1989. Oxime esters of substituted quinolin-8-carboxylic acids and thereof as herbicides. US patent 4808212.

Reil E, Hofle G, Draber W, Oettmeier W. 2001. Quinolones and their N-oxides as inhibitors of photosynthesis II and cytochrome b(6)/f-complex. Biochemistry Biophysics Acta 17, 1506(2), 127-32.

Reincke DM. 1999. 4-Chloroindole-3-acetic acid and plant growth. Plant growth Regulation 27, 3-13.

Reiner F, Astrid U, Christoph E, Kuck K-H, Stefan H, Axel T, Jörg K, Ulrike W-N, Astrid M-M. 2003. Biphenyl-substituted 4-hydroxy-quinolones and their use as pesticides and herbicides. WO2003010145.

Serban A. 1972. 3-Chloro-5-acetamideisoquinoline as a herbicide. US patents 930837.

Uknes SJ, Ho T-HD. 1984. Mode of Action of Abscisic Acid in Barley Aleurone Layers. Plant Physiology 75, 1126-1132.

Vencill WK. 2002. Herbicide Handbook. 8th Ed. Weed Science Society of America, Lawrence, KS.

Wuerzer B, Berghaus R. 1985. Substituted quinolinecarboxylic acid-new elements in herbicide. In: the 10th Asian Pacific Weed Science Society Conference pp 177-184.

Yasuo F, Hiroyuki N, Minoru S, Tsuneo I, Yugo I, Morio K. 1976. Indazole derivatives. Jpn Kokai Tokkyo Koho JP 51059862.

Yasuor H, Milan M, Echert JW, Fischer AJ. 2012. Quinclorac resisitance: a concerted hormonal and enzymatic effort in Echinochloa phllopogon. Pest Mangement. Science 68(1), 108-15.

Zhao Q, Liu S, Wang Q. 2009. Design, synthesis and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole or quinoline moieties. Journal of Agriculture Food Chemistry 8, 57(7) 2849-55.