Record Details

Synthesis and Characterization of N-Acylaniline Derivatives as Potential Chemical Hybridizing Agents (CHAs) for Wheat ( Triticum aestivum L.)

CMFRI Repository

View Archive Info
 
 
Field Value
 
Relation http://eprints.cmfri.org.in/9950/
 
Title Synthesis and Characterization of N-Acylaniline Derivatives as
Potential Chemical Hybridizing Agents (CHAs) for Wheat
( Triticum aestivum L.)
 
Creator Chakraborty, Kajal
Devakumar, C
 
Subject Bioactive compound
 
Description Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in
heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the
same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of
malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized
and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD
2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl
and aromatic domain were synthesized by condensation of substituted anilines with appropriate
diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such
as F/Br at the paraposition of the aryl ring were identified as the most potent CHAs, causing higher
induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues
like 4¢-fluoroacetoacetanilide (7) and ethyl 4¢-fluoromalonanilate (1), which induced 89.12 and 84.66%
male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of
chlorine atoms in the side chain led to an increase in the activity of 4¢-fluoro (23) and 4¢-bromo (24)
derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity
relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the
Swain-Lupton constant ( Fp) and negative contributions of the Swain-Lupton resonance constant
( R) for the aromatic substitution. The positive influences of parachor ( P) for the acyl domain have
been underlined. These leads will be significant in explaining the CHA fit in the macromolecular
receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in
pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.
 
Publisher American Chemical Society
 
Date 2006
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/9950/1/4.pdf
Chakraborty, Kajal and Devakumar, C (2006) Synthesis and Characterization of N-Acylaniline Derivatives as Potential Chemical Hybridizing Agents (CHAs) for Wheat ( Triticum aestivum L.). Journal of Agricultural and Food Chemistry, 54. pp. 6800-6808.