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

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Naslov:	The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates
Avtorji:	ID Iskra, Jernej (Avtor) ID Titan, Primož (Avtor) ID Meglič, Vladimir (Avtor)
Datoteke:	PDF - Predstavitvena datoteka, prenos (272,06 KB) MD5: DDDC58592DE97BEA4E336725895AF8EB PID: 20.500.12556/dirros/a7bf1aff-c40b-46e4-89c3-01bce68dddd3
Jezik:	Angleški jezik
Tipologija:	1.01 - Izvirni znanstveni članek
Organizacija:	KIS - Kmetijski inštitut Slovenije
Ključne besede:	fluorokemija, oksanilati, gametocidi, navadna
Status publikacije:	Objavljeno
Verzija publikacije:	Objavljena publikacija
Leto izida:	2013
Št. strani:	str. 561-568
Številčenje:	Vol. 60, no. 3
PID:	20.500.12556/DiRROS-792
UDK:	547.53
ISSN pri članku:	1318-0207
URN:	URN:NBN:SI:doc-LUK9YDML
COBISS.SI-ID:	27001127
Datum objave v DiRROS:	01.04.2015
Število ogledov:	4397
Število prenosov:	583
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Jezik:	Slovenski jezik
Povzetek:	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.
Ključne besede:	Chemical hybridizing agent, oxanilate, common wheat, heterosis, solvent-free synthesis

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