Synthesis and quantitative structure-activity relationships of oxanilates as chemical hybridizing agents for wheat (Triticum aestivum L.)

Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HD 2733, during two Rabi (winter) seasons, 2000-01 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25,containing 4-F, 4-Br, and 4-CF(3) aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure-activity relationship analysis revealed a direct relationship between F(p) and molecular mass but an inverse relationship between MR, E(S), and R in influencing the bioactivity. Several F(1) hybrids were developed using 5, and at least one showed heterosis.     

Synthesis and screening of anilides having olefinic and alkyl moiety in the side chain as chemical hybridizing agents for wheat (Triticum aestivum L.)

Induction of male sterility by deployment of chemical hybridizing agents (CHAs) holds immense potential in heterosis breeding of wheat. A total of 21 anilides having different aromatic substitutions and side-chain variation were synthesized and screened as CHAs on three genotypes of wheat viz., PBW 343, HW 2046, and HD 2733, at winter season. Various anilides having vinyl moiety in the acyl side chain were synthesized by condensation between substituted anilines with different esters or acid chlorides. Another lead in the form of N-alkyl anilines also became evident. The percent male sterility data caused by CHAs revealed the significant contribution of anilides containing vinyl double bond incorporated in the form of closed ring structure viz., furyl moiety as the side chain. 4'-Fluoro-furyl anilide (1) and 4'-bromo-furyl anilide (2) are found to be promising lead CHAs for the design of highly active molecules. QSAR analysis revealed a direct relationship of field effect exemplified by the Swain-Lupton constant F(p) for the aromatic substitution but an inverse relationship of molar refractivity MR for the side chain. The negative influences of parachor for the acyl domain have been underlined. The real guiding principle for selectivity of CHA action was found to be the pi value. The CHAs act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.     

Influence of edaphic factors on the mineralization of neem oil coated urea in four Indian soils

The utility of neem (Azadirachta indica A Juss) oil coated urea as a value-added nitrogenous fertilizer has been now widely accepted by Indian farmers and the fertilizer industry. In the present study, the expeller grade (EG) and hexane-extracted (HE) neem oils, the two most common commercial grades, were used to prepare neem oil coated urea (NOCU) of various oil doses, for which mineralization rates were assessed in four soils at three incubation temperatures (20, 27, and 35 degrees C). Neem oil dose-dependent conservation of ammonium N was observed in NOCU treatments in all of the soils. However, a longer incubation period and a higher soil temperature caused depletion of ammonium N. Overall, the nitrification in NOCU treatment averaged 56.6% against 77.3% for prilled urea in four soils. NOCU prepared from EG neem oil was consistently superior to that derived from hexane-extracted oil. The performance of NOCUs was best in coarse-textured soil and poorest in sodic soil. The nitrification rate (NR) of the NOCUs in the soils followed the order sodic > fine-textured > medium-textured > coarse-textured. The influence of edaphic factors on NR of NOCUs has been highlighted. The utility of the present study in predicting the performance of NOCU in diverse Indian soils was highlighted through the use of algorithms for computation of the optimum neem oil dose that would cause maximum inhibition of nitrification in any soil.     

EFFECT OF NEEM-OIL COATED PRILLED UREA WITH VARYING THICKNESS OF NEEM-OIL COATING AND NITROGEN RATES ON PRODUCTIVITY AND NITROGEN-USE EFFICIENCY OF LOWLAND IRRIGATED RICE UNDER INDO-GANGETIC PLAINS

The nitrogen (N) fertilizer-use efficiency (20–50%) is low in rice fields in India. The neem-oil coated urea can increase N-use efficiency in lowland rice, but the desirable thickness of neem-oil coating onto urea is not known yet. Therefore, field experiments were conducted during kharif (rainy) season years 2004 and 2005 at the Research Farm of Indian Agricultural Research Institute, New Delhi to know the suitable thickness of neem-oil coating on prilled urea (PU) for increased N-use efficiency and yield. The treatments comprised of twelve combinations of four N sources (PU coated with neem-oil thickness of 0, 500, 1000 and 2000 mg kg^?1 PU) and three N levels (50, 100, and 150 kg N ha^?1) plus a no-N control. Prilled urea (PU) refers to the common urea available commercially in prills, which is different from urea super granules. Application of urea coated with neem-oil thickness of 1000 mg kg^?1 PU resulted in significantly higher growth, yield parameters, grain yield, N uptake, and efficiency of aromatic rice (Oryza sativa L.) over uncoated PU. Nitrogen application at 122 kg ha^?1 was optimum for increased yield of rice. Nitrogen-use efficiency decreased significantly and substantially with each successive increase in levels of N from 50 to 150 kg ha^?1.     

Dietary administration of natural immunostimulants on growth performance,haematological, biochemical parameters and disease resistance of Asian Sea bass Lates calcarifer (Bloch, 1790)

This study was aimed to address the promising evaluation of Cissus quadrangularis plant (stem) and lipopolysaccharide (LPS from bacteria) supplemented diets on innate immune response in Lates calcarifer fingerlings against Aeromonas hydrophila infection. Fingerlings were fed supplemented diets containing four different concentrations of C. quadrangularis (0.5, 1.0, 1.5 and 2.0 g kg^?1 feed), LPS (25, 50, 75 and 100 mg kg^?1 feed) and control (normal formulated diet) for 60 days. The fish fingerlings fed supplemented diet displayed significant differences (P < 0.05) in specific growth rate (SGR) and relative percentage survival compared to the control group fed without C. quadrangularis and LPS‐supplemented diet. Fingerlings were injected intraperitoneally with 100 μL lethal dose of A. hydrophila containing 1 × 10⁶ CFU g^?1. Supplementation of C. quadrangularis and LPS diet significantly increased biochemical profile such as protein, lipid and carbohydrate content, haematological parameters of L. calcarifer fingerlings in different experimental periods when compared with the control group. Dietary doses of C. quadrangularis and LPS‐supplemented diet significantly influenced growth performance and increased survival rate in L. calcarifer fingerlings against A. hydrophila infection.     

Influence of physicochemical parameters of neem (Azadirachta indica A Juss) oils on nitrification inhibition in soil

The technology for the production of neem oil coated urea (NOCU) developed by the Indian Agricultural Research Institute is in the pipeline for adaption by several Indian fertilizer industries. Use of nitrification inhibitors is one of the methods of improving the nitrogen use efficiency (NUE) of nitrogenous fertilizers in agriculture. However, standard specifications for the neem oil as a raw material of NOCU are desired. Accordingly, the present study was undertaken to evaluate 25 samples of neem oils comprising 11 samples of expeller grade (EG) oils, 8 samples of cold-pressed (CP) oils, 3 samples of solvent-extracted oils, and 2 commercial formulations. NOCU was prepared using these oils (5000 ppm of urea-N). The soils fertilized with NOCUs (200 ppm of urea-N) were incubated at 27 degrees C and 50% water-holding capacity for a period of 15 days. Nitrapyrin (0.5% of N) coated urea served as the reference and prilled urea as control. Samples were analyzed for NH4+-N, NO2--N, and NO3--N using standard methods. The percent nitrification inhibition (NI) was calculated, and the results revealed that all of the neem oils caused NI ranging from 4.0 to 30.9%. Two samples of EG oils and two commercial formulations were found to be the best, causing 27.0-30.9% NI. Iodine, acid, and saponification values and meliacin content of all of the oils were analyzed and correlated with NI. The results revealed the direct influence of meliacin content of the neem oils on NI, which, however, was found to be negatively correlated with saponification and iodine values. There is, therefore, a need to introduce new Bureau of Indian Standards (BIS) specifications for neem oils as raw materials of NOCU.     

Evaluation of chemical compounds for induction of male sterility in wheat (Triticum aestivum L.)

The short-list of eleven chemical hybridizing agents (CHAs) showing 98% or more induction of male sterility were identified following application at the pre-meiotic stage of wheat. Among ethyl oxanilates, 4-fluoro (CHA A1), 4-bromo (CHA A2), 4-trifluoromethyl (CHA A5), and 4-cyano (CHA A3) derivatives; and among pyridones, 4-chloro (CHA B3), 4-fluoro (CHA B1), 4-bromo (CHA B2), and 4-trifluoromethyl (CHA B6) derivatives were the most promising. These agents showed no adverse effects on plant growth and yield. Ethyl 4-fluoro oxanilate (CHA A1) was tested on 29 wheat genotypes at 1500ppm and induced 99.76± 0.37% male sterility. Ethyl 4-fluoro oxanilate residues were non-detectable in grain and husk and thus appeared to have no lasting residue effects. An erratum to this article can be found at     

Quantitative structure-activity relationship analysis as a tool to evaluate the mode of action of chemical hybridizing agents for wheat (Triticum aestivum L.)

Augmentation of wheat production calls for introduction of wheat hybrids in cultivation. In the absence of viable alternative technology of hybrid wheat development, chemical induction of male sterility mediated technology based on chemical hybridizing agents (CHAs) holds a great potential. The QSAR method was applied to two families of CHAs in the N-acylanilines and pyridone class of chemistry. The models for each CHA family gave good correlation between the variations in log percent of male sterility and the steric-electrostatic properties of the sets. QSAR analysis has revealed a direct relationship of the Swain-Lupton constant F(p) and molecular mass but an inverse relationship of MR, ES, and Swain-Lupton resonance constant R in influencing the bioactivity in the N-acylanilines. QSAR analysis of four parent families consisting of two training sets each of pyrid-2-ones and prid-4-ones revealed the positive contributions of field effect exemplified by the Swain-Lupton field constant (F) and the negative contributions of the molar refractivity (MR) of aromatic substituents in all but one training set. The QSAR models also indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. These leads will be useful in explaining the CHA binding fit in the macromolecular receptor site.     

Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)

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 para position 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.