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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: 4766 Downloads: 674 Metadata:    Cite this work Plain text BibTeX EndNote XML EndNote/Refer RIS ABNT ACM Ref AMA APA Chicago 17th Author-Date Harvard IEEE ISO 690 MLA Vancouver : Copy citation

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Record is a part of a journal

Title:	Acta chimica slovenica
Shortened title:	Acta chim. slov.
Publisher:	Slovensko kemijsko društvo, =Slovenian Chemical Society
ISSN:	1318-0207
COBISS.SI-ID:	14086149

Secondary language

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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