The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates

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Title:	The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates
Authors:	ID Iskra, Jernej (Author) ID Titan, Primož (Author) ID Meglič, Vladimir (Author)
Files:	PDF - Presentation file, download (272,06 KB) MD5: DDDC58592DE97BEA4E336725895AF8EB PID: 20.500.12556/dirros/a7bf1aff-c40b-46e4-89c3-01bce68dddd3
Language:	English
Typology:	1.01 - Original Scientific Article
Organization:	KIS - Agricultural Institute of Slovenia
Keywords:	fluorokemija, oksanilati, gametocidi, navadna
Publication status:	Published
Publication version:	Version of Record
Year of publishing:	2013
Number of pages:	str. 561-568
Numbering:	Vol. 60, no. 3
PID:	20.500.12556/DiRROS-792
UDC:	547.53
ISSN on article:	1318-0207
URN:	URN:NBN:SI:doc-LUK9YDML
COBISS.SI-ID:	27001127
Publication date in DiRROS:	01.04.2015
Views:	4758
Downloads:	673
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Title:	Acta chimica slovenica
Shortened title:	Acta chim. slov.
Publisher:	Slovensko kemijsko društvo, =Slovenian Chemical Society
ISSN:	1318-0207
COBISS.SI-ID:	14086149

Language:	Slovenian
Abstract:	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.
Keywords:	Chemical hybridizing agent, oxanilate, common wheat, heterosis, solvent-free synthesis

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