Acetylation of 5-amino-1H-[1,2,4]triazole revisited

The products of the acetylation reactions of the common herbicide 5-amino-1H-[1,2,4]triazole were investigated using HPLC, GC-MS, 1H NMR, and FTIR spectroscopy. The conventional annular monoacetylation procedures with acetyl chloride are not regioselective and furnish a mixture of isomers. Traditional diacetylation in neat acetic anhydride under reflux produces a mixture of di-, mono-, and triacetylated derivatives. By using equivalent amounts of acetic anhydride in a dimethylformamide solution, a rapid and selective annular monoacetylation of 5-amino-1H-[1,2,4]triazole was achieved. The monoacetylation proceeds via the formation of the intermediate, 1-acetyl-3-amino-1H-[1,2,4]triazole, which had not been observed previously and which undergoes transformation into the known 1-acetyl-5-amino-1H-[1,2,4]triazole. Neat acetic anhydride at room temperature affords the diacetylated derivative, 1-acetyl-3-(acetylamino)-1H-[1,2,4]triazole both from 5-amino-1H-[1,2,4]triazole itself and from either 1-acetyl-5-amino-1H-[1,2,4]triazole or 5-(acetylamino)-1H-[1,2,4]triazole. The atypical product of the second acetylation, 1-acetyl-5-(acetylamino)-1H-[1,2,4]triazole, has been identified. These results may be useful in the development of effective and selective preparative procedures for the acetylation of 5-amino-1H-[1,2,4]triazole.     

Chilling stress tolerance of two soya bean cultivars: Phenotypic and molecular responses

Chilling stress is a major factor limiting the yield of soya bean [Glycine max (L.) Merr.] on a global scale. However, the regulatory network that controls the chilling response of soya bean remains unclear. In the present study, phenotyping and quantitative analyses of miRNAs in soya bean under chilling stress were carried out to determine the impact of environmental constraints on soya bean productivity. Measurements done during soya bean growth in chilling along with the results of field trials indicated that the cultivars Augusta and Fiskeby V responded differently to low temperatures. Although chilling affected the reproductive development of both cultivars, the final seed output remained unchanged. The differential expression of miR169, miR319, miR397 and miR398 under cold stress was detected using ddPCR. Upon chilling in the reproductive stage, we found that these miRNAs had contrasting expression profiles in Augusta and Fiskeby V. A set of candidate target genes was predicted based on degradome sequencing data. A negative correlation was found between the expression of miR169, miR319 and miR398 and their targets in the roots of both cultivars. Our work elucidates the impact of chilling stress on the productivity of two soya bean cultivars and reveals the importance of miRNA involvement in the low temperature response.     

Effect of cold‐induced changes in physical and chemical leaf properties on the resistance of winter triticale (×Triticosecale) to the fungal pathogen Microdochium nivale

This study showed that several mechanisms of the basal resistance of winter triticale to Microdochium nivale are cultivar‐dependent and can be induced specifically during plant hardening. Experiments and microscopic observations were conducted on triticale cvs Hewo (able to develop resistance after cold treatment) and Magnat (susceptible to infection despite hardening). In cv. Hewo, cold hardening altered the physical and chemical properties of the leaf surface and prevented both adhesion of M. nivale hyphae to the leaves and direct penetration of the epidermis. Cold‐induced submicron‐ and micron‐scale roughness on the leaf epidermis resulted in superhydrophobicity, restricting fungal adhesion and growth, while the lower permeability and altered chemical composition of the host cell wall protected against tissue digestion by the fungus. The fungal strategy to access the nutrient resources of resistant hosts is the penetration of leaf tissues through stomata, followed by biotrophic intercellular growth of individual hyphae and the formation of haustoria‐like structures within mesophyll cells. In contrast, a destructive necrotrophic fungal lifestyle occurs in susceptible seedlings, despite cold hardening of the plants, with the host epidermis, mesophyll and vascular tissues being digested and becoming disorganized as a result of the low chemical and mechanical stability of the cell wall matrix. This work indicates that specific genetically encoded physical and mechanical properties of the cell wall and leaf tissues that depend on cold hardening are factors that can determine plant resistance against fungal diseases.     

Genotype-by-environment interaction of barley DH lines infected with Fusarium culmorum (W.G.Sm.) Sacc.

Infection of plants by pathogens is a biotic environmental stress. Barley plants are infected, among others, by Fusarium culmorum—a pathogen affecting seedling, head, root and stem. The infection can result in reduced yield and grain quality. The aim of the study was to compare the reaction of inoculated and non-inoculated barley doubled haploids (DHs) with F. culmorum in various environments. Thirty-four genotypes were inoculated with an isolate of F. culmorum. The experiment was carried out over 6 years. Kernel weight per spike, 1000-kernel weight and percentage of plump kernels were observed in control and inoculated plants. Genotype-by-environment (GE) interaction and its structure with reference to the environments and genotypes were analysed. Additional information about the sensitivity of healthy and infected genotypes to environments was determined by the regression analysis. Statistical computation was made using the SERGEN software. Lines were considered as unstable when their GE interaction was significant at P = 0.05. Unstable genotypes were classified as intensive or extensive according to the results of the regression analysis. It was found that infection with Fusarium decreased the stability of barley lines in different environments. Interaction of unstable infected genotypes with environments, most often, could not be explained by the regression—their response to various environmental conditions appeared to be unpredictable. Selection of lines less susceptible to biotic and abiotic stresses was possible due to comparison of classification of healthy and infected lines, which was made based on their main effects and GE interaction.     

Simultaneous selection for yield-related traits and susceptibility to Fusarium head blight in spring wheat RIL population

Fusarium head blight (FHB), caused by the fungal plant pathogen Fusarium, is a fungal disease that occurs in wheat and can cause significant yield and grain quality losses. The present paper examines variation in the resistance of spring wheat lines derived from a cross between Zebra and Saar cultivars. Experiments covering 198 lines and parental cultivars were conducted in three years, in which inoculation with Fusarium culmorum was applied. Resistance levels were estimated by scoring disease symptoms on kernels. In spite of a similar reaction of parents to F. culmorum infection, significant differentiation between lines was found in all the analyzed traits. Seven molecular markers selected as linked to FHB resistance QTLs gave polymorphic products for Zebra and Saar: Xgwm566, Xgwm46, Xgwm389, Xgwm533, Xgwm156, Xwmc238, and Xgwm341. Markers Xgwm389 and Xgwm533 were associated with the rate of Fusarium-damaged kernels (FDK) as well as with kernel weight per spike and thousand kernel weight in control plants. Zebra allele of marker Xwmc238 increased kernel weight per spike and thousand kernel weight both in control and infected plants, whereas Zebra allele of marker Xgwm566 reduced the percentage of FDK and simultaneously reduced the thousand kernel weight in control and infected plants.     

Micro-hydrological and micro-meteorological controls on survival and population growth of the whorl snail Vertigo geyeri Lindholm, 1925 in groundwater fed wetlands

Vertigo geyeri is a rare, tiny species of mollusc, living in calcareous, spring fed wetlands. It is considered to be threatened within the EU community; therefore it is protected under Annex II of the EU Habitat Directive (92/43/EEC). This snail has very specific micro-habitat requirements, which up to now were largely unknown. This study was initiated to provide more information on the detailed micro-hydrogeological and micro-meteorological requirements for this microscopic species in order to manage their future existence on Pollardstown Fen, Ireland and at other sites. The micro-habitat of the snail was studied during an extensive research project carried on Pollardstown Fen in Ireland during the period 2002-2005 being the first national (and possibly international) study of that scale. The results show that high relative humidity (above 80%) and close proximity to a phreatic water surface (approximately 0.1 m below ground surface) are the most important factors for maintaining populations of the snail.     

Barley varieties in semi‐controlled and natural conditions—Response to water shortage and changing environment

The yield potential of 60 spring barley varieties was examined under controlled drought and natural conditions in the years 2011–2013. The studied varieties were genotyped with the 1536‐SNP barley oligonucleotide assay. In experiments with controlled drought conditions, the grain yield, 1,000‐grain weight, number of productive tillers and length of the main stem were measured. Physicochemical properties such as the specific surface area, water adsorption energy, fractal dimension and nanopore radius of the plant leaves were determined and correlated with yield‐forming traits. Field trials were conducted over 3 years at 14 locations, where along with the yield‐related traits, monthly rainfall and average temperature were monitored. Five varieties of high yield and five varieties relatively stable under both semi‐controlled and natural conditions were distinguished. The yield‐related traits observed in various locations were related to environmental variables relevant to water availability. The sum of the rainfall in April and May was negatively correlated with the 1,000‐grain weight and positively with the plant height. Positive relationships were found between plant height and temperatures in June and July. Five markers detected earlier as linked to the quantitative trait loci in the mapping populations were identified to have a coherent effect among varieties of various pedigree.