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

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.

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    Abstract

    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.

    Item Type: Article
    Uncontrolled Keywords: Chemical hybridizing agents; N-acylanilines; QSAR; malonanilates; anilides; wheat
    Subjects: Fish Biotechnology > Bioactive compound
    Divisions: CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI-Kochi > Marine Biotechnology
    Depositing User: Arun Surendran
    Date Deposited: 26 Feb 2014 10:14
    Last Modified: 10 Jul 2017 10:56
    URI: http://eprints.cmfri.org.in/id/eprint/9950

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