Soil organic matter chemistry. Part 1. Characterization of several humic preparations by proton and carbon‐13 nuclear magnetic resonance spectroscopy

Both laboratory and commercial preparations of humic substances (HSs) such as fulvic acids and humic acids along with HC1‐HF preparation of Manitoba peat soil organic matter were characterized using Fourier Transformation (FT) proton (¹H) and carbon‐13 (¹³C) nuclear magnetic resonance (NMR) spectroscopy. All the samples were dissolved in a solution of 0.4 N NaOD in D₂O. In the case of ‘H‐NMR spectroscopy, all the investigated humic samples displayed resonance absorption peaks in the region of 1–4 ppm indicating the likely presence of aliphatic protons in the preparations. However, with the exception of one fulvic acid preparation (extracted from Manitoba Carrol clay‐loam soil with 0.5 N NaOH), ¹H‐NMR spectra of all other samples provided evidence for strong aromatic character. The aliphatic and aromatic characteristics of such samples of HSs were further confirmed with the aid of ¹³C‐NMR spectra.     

Photocatalytic degradation of chlorophenols using Ru(bpy) 3 2+ /S2O 8 2−

Advanced oxidation processes, such as photocatalysed oxidation, provide an important route for degradation of wastes. In this study, the lowest excited state (³MLCT) of Ru(bpy)₃²⁺ is used to break down chlorophenol pollutant molecules to harmless products. This has the advantage of using visible light and a short-lived catalytically active species. Photolysis of deaerated aqueous solutions of a variety of mono- and poly-substituted chlorophenols has been followed in the presence of Ru(bpy)₃²⁺/S₂O₈²⁻ with near visible light (λ > 350 nm) by UV/visible absorption spectroscopy, luminescence, potentiometry, NMR and HPLC techniques. Upon irradiation, a decrease is observed in the chlorophenol concentration, accompanied by the formation of Cl⁻, H⁺ and SO₄²⁻ ions as the main inorganic products. Benzoquinone, phenol, dihydroxybenzenes and chlorinated compounds were the dominant organic products. As the ruthenium(II) complex is regenerated in the reaction, the scheme corresponds to an overall catalytic process. The kinetics of the rapid chlorophenol photodechlorination has been studied, and are described quite well by pseudo-first order behaviour. Further studies on this were made by following Cl⁻ release with respect to the initial Ru(bpy)₃²⁺ and S₂O₈²⁻ concentrations. A comparison is presented of the photodechlorination reactivity of the mono and polychlorophenols studied at acidic and alkaline pH.     

Stable C and N isotope analysis elucidated the importance of zooplankton in a tropical seagrass bed of Santiago Island,Northwestern Philippines

The role of zooplankton in a tropical seagrass ecosystem was investigated in milkfish farms pollution-impacted and -unimpacted seagrass beds in Santiago Island coral reefs, Northwestern Philippines. The aim was to compare between the two sites: (1) abiotic factors and zooplankton community parameters, and (2) the trophic structure using C and N stable isotopes. Low water (98–119?mV) and sediment (–121 to ?138?mV) Oxidation Reduction Potential values indicated a reducing environment in the impacted site. Zooplankton in the impacted site showed the typical community response to eutrophication (low diversity, but high total abundance due to the dominance of the cyclopoid copepod Oithona oculata), generally few elevated δ¹⁵N values, but a significant shift towards depleted ¹³C due to the organic enrichment of fish-farm feeds. Apart from suggesting a highly complex food web with POM and zooplankton as main food sources in the unimpacted site, the Bayesian mixing model simulation generated reduced complexity in feeding interactions between basal sources, zooplankton, and fish including adults of a key fish species, Siganus fuscescens, in the impacted sites. In this study, C and N stable isotope analysis has clarified the importance of zooplankton as fish prey in a seagrass bed food web.     

A sensitive method for determining nitrogen-15 isotope in urea

A method is presented in which the ¹⁵N at.% of urea is determined with high precision on liquid samples containing as little as 10 nmol of urea. The method involves removal of interference from NH₄ ⁺ initially present in the sample by cation exchange. Urea in the sample is subsequently hydrolyzed to NH₄ ⁺ by the enzyme urease. Liberated NH₄ ⁺ is separated from the alkaline sample by diffusion as NH₃ through a helium gas phase where it is finally oxidized to N₂ by reaction with hypobromite iodine. The isotopically labeled N₂ thus formed is mixed with the N₂ initially present in the sample, and the ¹⁵N at.% of urea is calculated from the relative amounts of ¹⁴N¹⁵N and ¹⁵N¹⁵N by means of the isotope pairing principle. The presented method for ¹⁵N-urea analysis proved to be precise (SE < 0.4 at.%, n = 5), when applied on both marine and freshwater samples with an ¹⁵N enrichment >1 at.%, and interference was found only from volatile methyl amines. Received: 19 September 1996 / Accepted: 25 October 1996     

Toxicity of endosulfan on growth,photosynthesis, and nitrogenase activity in two species of Nostoc (Nostoc muscorum and Nostoc calcicola)

Treatments of the cyanobacteria Nostoc muscorum and Nostoc calcicola with the insecticide endosulfan (5, 10, and 20?µg?mL^?1) inhibited growth, photosynthetic pigments, photosynthetic, and nitrogenase activities. The sensitivity of N. muscorum to endosulfan was higher than that of N. calcicola. The toxic effect of endosulfan was more pronounced on phycocyanin; however, a considerable reduction in chlorophyll a and carotenoids was also noticed. ¹⁴C-fixation appeared to be more sensitive to the insecticide than photosynthetic oxygen evolution. Endosulfan caused strong inhibition of photosystem (PS) II activity whereas PS I was least affected. The inhibition of PS II activity was partially restored by electron donors (DPC, NH₂OH, and MnCl₂) at low dose of endosulfan. Nitrogenase activity was significantly suppressed in both species by the endosulfan at high dose (20?µg?mL^?1). On the basis of our comparative analysis, N. calcicola was found to be endosulfan resistant and can be used in paddy fields for better productivity under pesticide stress.     

Metabolic responses in zebrafish (Danio rerio) exposed to zinc and cadmium by nuclear magnetic resonance -based metabolomics

Heavy metals are common marine and soil pollutants that are mainly the result of industrial activity, and are a threat to the environment and human health. In this study, ¹H nuclear magnetic resonance (NMR)-based metabolomics was applied to adult Danio rerio to monitor the metabolic change as a response to ZnCl₂ and CdCl₂ exposure at different concentrations for 72?h. NMR spectroscopy was used to identify and quantify the metabolites extracted from D. rerio. The metabolite profiles of the control and heavy metal exposed group were classified by partial least squares – discriminant analysis (PLS-DA) analysis, and potential contaminant-specific biomarkers were suggested. For the ZnCl₂-exposed zebrafish, the levels of ATP, aspartate and NAD⁺ were increased, whereas the levels of formate, inosine, hypoxanthine and succinate decreased. In addition, the CdCl₂-exposed zebrafish showed an increase in the levels of ATP and formate and a decrease in the levels of glutamate, inosine and glutathione. Overall, Zn and Cd may lead to neurotoxicity, disturbances in the energy metabolism and oxidative stress. Our finding demonstrated that the application of NMR-based metabolomics might be useful for detecting the toxicity caused by sub-lethal concentrations of heavy metal contaminants in the environment.     

Nitrogen fixation on a coral reef

Acetylene reduction was used to assess nitrogen fixation on all major substrates at all major areas over a period of 1 to 6 yr (1980–1986) at One Tree Reef (southern Great Barrier Reef). Experiments using ¹⁵N₂ gave a ratio of 3.45:1.0 for C₂H₂ reduced:N₂ fixed. Acetylene reduction was largely light-dependent, saturated at 0.15 ml C₂H₂ per ml seawater, and linear over 6 h. High fixation was associated with two emergent cyanophyte associations, Calothrix crustacea and Scytonema hofmannii, of limited distribution. Subtidally, the major contribution to nitrogen fixation came from well-grazed limestone substrates with an epilithic algal community in the reef flat and patch reefs (3 to 15 nmol C₂H₄ cm^-2 h^-1). Similar substrates from the outer reef slope showed lower rates. Nitrogen fixation on beach rock, intertidal coral rubble, reef crest and lagoon sand was relatively small (0.3 to 1.0 nmol C₂H₄ cm^-2 h^-1). Seasonal changes in light-saturated rates were small, with slight reduction only in winter. Rates are also reported for experimental coral blocks (13 to 39 nmol cm^-2 h^-1) and for branching coral inside and outside territories of gardening damselfish (3 to 28 nmol cm^-2 h^-1). This work supports the hypothesis that the high nitrogen fixation on the reef flat and patch reefs of the lagoon (34 to 68 kg N ha^-1 yr^-1) is because these subtidal areas support highly disturbed communities with the greatest abundance of nitrogen-fixing cyanophyte algae. It is calculated from a budget of all areas that One Tree Reef has an annual nitrogen fixation rate of 8 to 16 kg N ha^-1 yr^-1.     

Nitrogen-fixation by cyanobacteria associated withCodium fragile (Chlorophyta): Environmental effects and transfer of fixed nitrogen

N₂-fixation associated with the green macroalgaCodium fragile subsp.tomentosoides (van Goor) Silva from Long Island, New York, USA, was attributable to several species of endophytic cyanobacteria. Rates of N₂-fixation ranged from 0.03 to 3.2µg N g^–1 dry wt h^–1 in freshly collected plants from several sites. Growth of the cyanobacteria appeared to be light-limited, due to the transmission of only 5 to 10% of incident light through the pigmented surface-layer of the macroalga. Daily irradiance was the most important factor determining both abundance of cyanobacterial cells and rate of N₂-fixation. The rate was also affected by instantaneous irradiance, and increased twofold from dark to ambient surface irradiance. Rates were reduced at low temperature (8°C) but showed no temperature effect between 12° and 26°C. External concentrations of dissolved inorganic nitrogen (DIN) up to 20µM did not influence N₂-fixation rate, but long-term exposure to 60µmol l^–1 d^–1 of NH ₄ ⁺ caused a reduction in the rate. InC. fragile grown under high daily irradiance and low external DIN concentration, ~50% of the assimilated-N was attributable to N₂-fixation. However, chlorophyllb extracted from plants grown with¹⁵N₂ showed an atom % excess¹⁵N of less than 0.1, suggesting that only a small proportion of the bacterially fixed-N was transferred to the seaweed. The association betweenC. fragile and its endophytic cyanobacteria appears to be based primarily on microhabitat suitability, rather than mutual metabolic dependence. It is doubtful that N₂-fixation by cyanobacteria is important to the ecological success of this seaweed species.     

Alterations in serum electrolyte levels after dimethoate exposure and recovery in the freshwater air-breathing catfish,Heteropneustes fossilis (Bloch)

Dimethoate, a moderately toxic insecticide, has a wide range of agricultural and domestic applications. Like other organophosphates, dimethoate has anticholinesterase activity. Fish are non-target organisms, inadvertently exposed to pesticides and their metabolic products. The present study includes short-term (96 h) and long-term (36 d) effects of dimethoate exposure on some serum electrolytes Ca²⁺, Mg²⁺, and Pi in the freshwater air-breathing catfish Heteropneustes fossilis. The concentration of dimethoate for short-term exposure was 2.24 mg L^?1 (75% of 96 h LC₅₀) and for long-term exposure 0.75 mg L^?1 (25% of 96 h LC₅₀). The study includes the recovery pattern in serum electrolytes after placing the fish in pesticide-free water. Fish show hypocalcemia, hypermagnesemia, and hyperphosphatemia after short-term and long-term exposure to dimethoate. When placed in pesticide-free water, these electrolytes exhibit recovery towards normalization, indicating significant (p < 0.05) recovery.     

Optimum Nitrogen Use and Reduced Nitrogen Loss for Production of Rice and Wheat in the Yangtse Delta Region

A long-term field and lysimeter experiment under different amount of fertilizer-N application was conducted to explore the optimal N application rates for a high productive rice–wheat system and less N leaching loss in the Yangtse Delta region. In this region excessive applications of N fertilizer for the rice–wheat production has resulted in reduced N recovery rates and environment pollution. Initial results of the field experiments showed that the optimal N application rate increased with the yield. On the two major paddy soils (Hydromorphic paddy soil and Gleyed paddy soil) of the region, the optimal N application rate was 225–270 kg N hm^–2 for rice and 180–225 kg N hm^–2 for wheat, separately. This has resulted in the highest number of effective ears and Spikelets per unit area, and hence high yield. Nitrogen leaching in the form of NO ₃ ^– -N occurs mainly in the wheat-growing season and in the ponding and seedling periods of the paddy field. Its concentration in the leachate increased with the N application rate in the lysimeter experiment. When the application rate reached 225 kg N hm^–2, the concentration rose to 5.4–21.3 mgN l^–1 in the leachate during the wheat-growing season. About 60% of the leachate samples determined contained NO ₃ ^– -N beyond the criterion (NO ₃ ^– -N 10 mg l^–1) for N pollution. In the field experiment, when the N application rate was in the range of 270–315 kg hm^–2, the NO ₃ ^– -N concentration in the leachate during the wheat-growing season ranged from 1.9 to 11.0 mg l^–1. About 20% of the leachate samples reached close to, and 10% exceeded, the criterion for N pollution. Long-term accumulation of NO ₃ ^– -N from leaching will no doubt constitute a potential risk of N contamination of the groundwater in the Yangtse Delta Region.     

Use of multiple tools to assess the feeding preference of coastal dolphins

The feeding preferences of the coastal dolphins Pontoporia blainvillei and Sotalia guianensis in south-eastern Brazil (21o18′S–22o25′S) were assessed through the prey’s index of relative importance (IRI), total mercury concentration (Hg_tot), and stable isotopic (δ¹⁵N and δ¹³C) to compare their efficiency in the discrimination of prey contribution to the predators’ diet. The IRI was the best tool to describe the dolphins’ preference, while Hg_tot and δ¹⁵N seemed to be efficient as a trophic marker when the diet is made up of prey of varying sizes, as observed in S. guianensis. Both dolphins presented lighter δ¹⁵N than their prey species, which is an unusual pattern. However, as the sample size to isotope ratios analysis was small, especially to the dolphins, the results should be considered with caution, and further studies are necessary to corroborate these findings. The δ¹³C values characterized a typical coastal food chain, confirming the preferential area of these species.     

Equation for isotope accumulation in products and biomass as a way to reveal the pathways in mesophilic methanol methanization by microbial community

Isotope-labelling of substrate is used to reveal the methabolic pathways of substrate transformation by microbial community. In this paper, in order to describe the batch mesophilic anaerobic methanization of ¹³C-labelled methanol and microbial ecology analysis (Li et al., 2008), an equation for the isotope accumulation in products and biomass was included into the basic mathematical model based on stoichiometric chemical reactions. The higher was the isotope level in substrate, the larger fraction of ¹³C accumulated in products and biomass. Acetate, total organic and inorganic carbon (TOC, TIC) concentrations and methane production were used for the model calibration, whereas ¹³C enrichment of acetate, TIC and biomass were used for model validation. In the model, chemical transformations including methanol and acetate oxidation, homoacetogenesis, hydrogenotrophic and aceticlastic methanogenesis were considered. The rate-limiting reactions were methanol and acetate consumption. According to the model, homoacetogens performing acetate formation and oxidation were competed with hydrogenotrophic methanogens for hydrogen. Biphasic methane production was due to hydrogenotrophic methanogenesis in the first phase and due to acetiticlastic and hydrogenotrophic methanogenesis following acetate oxidation in the second phase.     

Recycle of buried macroalgal detritus in sediments: use of dual-labelling experiments in the field

In intertidal sediments, burial and decomposition of macroalgal detritus can fuel the sediment of carbon (C) and nitrogen (N), which can be either promptly mineralised or assimilated to enter the food web. This study investigates the transfer of algal-derived C and N to the sediment and to the infauna feeding primarily on benthic diatoms. Thalli of Ulva spp. were ¹³C- and ¹⁵N-labelled in the mesocosm and frozen to create detritus. Thawed macroalgae were, then, buried in the sediment of an intertidal sand-flat forming a mosaic of small patches (50 × 50 cm²) enriched with the macroalgae interspersed with bare sediment. The area was dominated by Corophium volutator and Hydrobia ulvae. The uptake of ¹³C and ¹⁵N was measured in the residual macroalgae, in the sediment and in those animals. Decomposition of detritus was rapid and after 4 weeks the residual biomass was 3% the amount added. Algal-derived ¹³C and ¹⁵N were moved to the sediment. The total amount of ¹³C and ¹⁵N retained in the sediment after completing the decomposition was 3.4 ± 0.5% ¹³C and 2.7 ± 0.6% ¹⁵N the amount decomposed. During the first 2 weeks more N than C was assimilated (1.7% ¹³C and 13.5% ¹⁵N). During the remaining two weeks, N was released from the sediment, while there was little accumulation of C (+6.4 ± 2.0 % ¹³C and −7.7 ± 3.8% ¹⁵N). At the end of the decomposition, animals were ¹⁵N- and ¹³C-labelled. Considering the total accumulation of label in the sediment, they accounted for 3.5 ± 1.8% ¹³C and 25.8 ± 12.9 % ¹⁵N. Similarly, considering the mass of the heavy isotopes gained (¹³C) or lost (¹⁵N) during the remaining 2 weeks, the animals accounted for 4.7 ± 2.1% of the ¹³C in excess and for 18.6 ± 9.1% of the ¹⁵N loss. The transfer of C and N to the sediment and to the surface deposit-feeders can be a relevant mechanism to remove the excess of detritus from the sediment.     

Coral mucus stable isotope composition and labeling: experimental evidence for mucus uptake by epizoic acoelomorph worms

Mucus released by scleractinian corals can act as an important energy and nutrient carrier in coral reef ecosystems, and a distinct isotopic signature would allow following the fate of this material. This study investigates the natural C and N stable isotopic signatures of mucus released by four scleractinian coral genera (Acropora, Fungia, Pocillopora and Stylophora) in comparison with those of suspended particulate organic matter (POM) in seawater of a Northern Red Sea fringing coral reef near Aqaba, Jordan. The natural δ¹³C and δ¹⁵N signatures of coral mucus differed significantly from seawater POM for the majority of seasonal comparisons, but were inappropriate for explicit tracing of mucus in the coral reef food web. Thus, a labeling technique using stable isotope tracers (¹³C and ¹⁵N) was developed that produced δ¹³C values of up to 122 ± 5‰ (mean ± SE) and δ¹⁵N of up to 2,100 ± 151‰ in mucus exuded by Fungia corals. ¹³C and ¹⁵N-enriched compounds were rapidly (within 3 h) and light-dependently transferred from the endosymbiotic zooxanthellae to the mucus-producing coral host. The traceability of ¹⁵N-labeled mucus was examined by evaluating its uptake and potential utilization by epizoic acoelomorph Waminoa worms naturally occurring on a range of scleractinian coral taxa. This tracer experiment resulted in uptake of coral mucus by the coral-associated acoelomorphs and further demonstrated the possibility to trace stable isotope-labeled coral mucus by revealing a new trophic pathway in coral reef ecosystems.     

Evidence for benthic primary production support of an apex predator–dominated coral reef food web

Five hundred and ninety-nine primary producers and consumers in the Papahānaumokuākea Marine National Monument (PMNM) (22°N–30°N, 160°W–180°W) were sampled for carbon and nitrogen stable isotope composition to elucidate trophic relationships in a relatively unimpacted, apex predator–dominated coral reef ecosystem. A one-isotope (δ¹³C), two-source (phytoplankton and benthic primary production) mixing model provided evidence for an average minimum benthic primary production contribution of 65 % to consumer production. Primary producer δ¹⁵N values ranged from ?1.6 to 8.0 ‰ with an average (2.1 ‰) consistent with a prevalence of N₂ fixation. Consumer group δ¹⁵N means ranged from 6.6 ‰ (herbivore) to 12.1 ‰ (Galeocerdo cuvier), and differences between consumer group δ¹⁵N values suggest an average trophic enrichment factor of 1.8 ‰ Δ¹⁵N. Based on relative δ¹⁵N values, the larger G. cuvier may feed at a trophic position above other apex predators. The results provide baseline data for investigating the trophic ecology of healthy coral reef ecosystems.     

Movement and transformation of35S-labelled sulphate in the soil of a heavily polluted site in the Northern Czech Republic

Changes in chemistry and vertical distribution of³⁵S were investigated in column experiments using intact topsoil and repacked mineral soil horizons 1 to 20 weeks after tracer application (901 kBq³⁵S-SO₄ ^2– per column 6.5 cm in diameter). Horizons O, A, AE and Bvs of an Orthic Podzol were incubated at 20°C and wetted twice a week with 11 mm of natural throughfall precipitation (38.5 mg S0₄ ^2– L^–1-, pH 3.3). The top 35 cm of the soil contained 1,290 kg S ha^–1, or 18 times more than is the annual atmospheric S input (71.4 kg S ha^–1 yr^–1). Of this amount, 17.8 % was stored as inorganic sulphate S, 4.6 % as reduced inorganic S, and 77.6 % as organic S. In O + A and AE, free sulphate was the most abundant³⁵S form, while in Bvs the 35S activity of free and adsorbed sulphate was similar. The proportion of adsorbed sulphate increased with depth, averaging 23, 30 and 47 % of total inorganic sulphate³⁵S in O + A, AE and Bvs, respectively. Total specific activity of chemically transformed³⁵S (i.e., of reduced inorganic S and organic S) constituted 3.4, 3.8 and 105 % of inorganic sulphate³⁵S activity in O + A, AE and Bvs, respectively, in averaged weeks 2–4, and 7.5, 6.4 and 39.6 % in averaged weeks 11–13 in O+A, AE and Bvs, respectively. The turnover time of C-bonded³⁵S was shorter than that of ester sulphate³⁵S. An increase in FeS_2– ³⁵S with time indicated anaerobic conditions suitable for bacterial sulphate reduction. After 13 weeks, 68 % of the tracer was found deeper than 8 cm below soil surface.     

Reduction of hexavalent chromium using fungi and bacteria isolated from contaminated soil and water samples

The reductive adsorption of hexavalent chromium (Cr⁶⁺) using six indigenous microorganisms isolated from contaminated soil and water samples was investigated. Quantification of Cr⁶⁺ reduction was determined using the 1,5-diphenylcarbazide method followed measuring the absorbance at OD₅₄₀. Bacterial isolates identified as Klebsiella pneumoniae, Bacillus firmus and Mycobacterium sp. were capable of absorbing Cr⁶⁺ efficiently into their biomass, whereas the fungal isolates, Aspergillus flavus, Aspergillus sp. and A. niger were capable of transforming Cr⁶⁺ to Cr³⁺ relative to cell-wall-binding properties. Infrared spectral analysis of functional groups showed that ?OH, ?NH₂ and C?O with conjugated ?NH were the binding groups responsible for adsorption of Cr⁶⁺ within the biomass of isolates. The data highlight the promising biotechnological application of these isolates in removing carcinogenic and mutagenic Cr⁶⁺ from contaminated ecosystems.     

Nitrogen fixation (acetylene reduction) in the phyllosphere of Thalassia testudinum

N₂ fixation (C₂H₂ reduction) associated with the leaves of the sea grass Thalassia testudinum was investigated at 5 sites in South Florida (Biscayne Bay) and one site in the Bahamas (Bimini Harbor). Significant activities were correlated with the occurrence of a heterocystous blue-green alga (Calothrix sp.) on the leaves. C₂H₂ reduction was not stimulated by organic compounds, either aerobically or anaerobically in the light or dark. Therefore, other physiological types of microbes were not important in N₂ fixation. Diurnal and seasonal variations in N₂ fixation occurred, with maximal rates during the daytime and in the late spring and early summer. N₂ fixation was negligible at four stations in Biscayne Bay. At the fifth station, near Fowey Rock, about 5 kg N ha^-1 year^-1 was fixed. In the summer, the N₂ fixed per day (4–5 mg N m^-2) could provide 4 to 23% of the foliar productivity demands of T. testudinum at this site and the station in Bimini Harbor. N₂ fixation at the periphery of a sea-grass patch, near Fowey Rock, could provide 8 to 38% of the daily nitrogen requirement for leaf production, and thereby might compensate for a less effective trapping and recycling of nitrogen from dead leaves in such regions.     

Nitrogen assimilation in the symbiotic marine algae Prochloron spp.

Prochloron spp. Lewin, 1977, from three species of ascidians [Lissoclinum patella (Gottschaldt, 1898), Trididemnum cyclops Michaelsen, 1921 and Diplosoma virens (Hartmeyer, 1909)] showed light-dependent assimilation of ¹⁵N-labelled ammonium sulphate. The ¹⁵N assimilated into glutamine was measured using the non-invasive technique of nitrogen-15 nuclear magnetic resonance (¹⁵N NMR).     

Synthesis and antifungal property of N,N′-bis(trans-cinnamaldehyde)-1,2-diiminoethane and its derivatives

N,N′-bis(trans-cinnamaldehyde)-1,2-diiminoethane and its derivatives were designed and synthesized. Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (¹H-NMR) techniques were applied to characterize chemical structures, and the filter paper disk method was used to test for antifungal effect of the products against Aspergillus niger, Paecilomyces variotii, and Paecilomyces lilacinus. Chemical structure charaterization showed that the products are target compounds. Antimicrobial experiment results indicated that N,N′-bis(trans-cinnamaldehyde)-1,2-diiminoethane displayed reliable antifungal effects against three fungi, and its antifungal effect is close to that of cinnamaldehyde. N,N′-bis(p-methoxy cinnamaldehyde)-1,2-diiminoethane and N,N′-bis(p-chlorocinnamaldehyde)-1,2-diiminoethane also showed antifungal effects at a low concentration. Of the two, N,N′-bis(p-methoxy cinnamaldehyde)-1,2-diiminoethane appeared to be more suitable as it was more effective at higher concentrations against Paecilomyces.