Synthesis and Screening of Anilides Having Olefinic and AlkyludMoiety in the Side Chain as Chemical Hybridizing Agents forudWheat ( Triticum aestivum L.)

摘要

Induction of male sterility by deployment of chemical hybridizing agents (CHAs) holds immenseudpotential in heterosis breeding of wheat. A total of 21 anilides having different aromatic substitutionsudand side-chain variation were synthesized and screened as CHAs on three genotypes of wheat viz.,udPBW 343, HW 2046, and HD 2733, at winter season. Various anilides having vinyl moiety in the acyludside chain were synthesized by condensation between substituted anilines with different esters orudacid chlorides. Another lead in the form of N-alkyl anilines also became evident. The percent maleudsterility data caused by CHAs revealed the significant contribution of anilides containing vinyl doubleudbond incorporated in the form of closed ring structure viz., furyl moiety as the side chain. 4¢-Fluorofuryludanilide (1) and 4¢-bromo-furyl anilide (2) are found to be promising lead CHAs for the design ofudhighly active molecules. QSAR analysis revealed a direct relationship of field effect exemplified byudthe Swain-Lupton constant Fp for the aromatic substitution but an inverse relationship of molarudrefractivity MR for the side chain. The negative influences of parachor for the acyl domain have beenudunderlined. The real guiding principle for selectivity of CHA action was found to be the ð value. TheudCHAs act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to anudimbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall byudpremature callase secretion.