20.500.12556/DiRROS-792 The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates Three derivatives of ethyl oxanilate were synthesized in order to test their application as gametocides on the hermaphrodite plants like common wheat (Triticum aestivum L.). A substituent at para position (F, Br, CN) of aniline defined its reactivity towards diethyl oxalate 2. Classical reaction in toluene was not selective and amidation occurred also at the second carbonyl groups of 2. Alternative synthesis under solvent-free conditions with application of low pressure for removal of EtOH provided selectively with ethyl oxanilate 3a and 3b. 4-Cyanoaniline did not react selectively and the corresponding ethyl oxanilate 3c was prepared from mono acid chloride of oxalic acid. Fluoro derivative 3a was found to be the only one that gives stable aqueous suspension for its application as chemical hybridizing agent for common wheat, while bromo- 3b and cyano- 3c analogues were not soluble enough and suspension was stable for less than 2 hours. Fluoro derivative had shown the best induction of male sterility, while in comparison with standard chemical hybridizing agent they were substantially less toxic for plant. fluorokemija oksanilati gametocidi navadna Chemical hybridizing agent oxanilate common wheat heterosis solvent-free synthesis true true true Angleški jezik Slovenski jezik Članek v reviji 2015-04-01 11:01:18 2015-04-01 11:47:18 2022-08-10 06:02:55 0000-00-00 00:00:00 2013 0 0 str. 561-568 no. 3 Vol. 60 2013 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.53 1318-0207 URN:NBN:SI:doc-LUK9YDML 27001127 14086149 RAZ_Iskra_Jernej_i2013.pdf RAZ_Iskra_Jernej_i2013.pdf 1 DDDC58592DE97BEA4E336725895AF8EB 964a5431c41a955ae863df29a0391ee48552d3bae445a78a35d3d06c0135021a a08474e3-17b4-11ed-b6b8-001a4af901a5 20.500.12556/dirros/a7bf1aff-c40b-46e4-89c3-01bce68dddd3 https://dirros.openscience.si/Dokument.php?lang=slv&id=883 Kmetijski inštitut Slovenije 0 0 0