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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

Six analogues of natural trans-4-butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and three derivatives, 11, 12, and 13, of Vince lactam (10) were synthesized and tested as fungistatic agents against Botrytis cinerea AM235, Penicillium citrinum AM354, and six strains of Aspergillus. Moreover, bioresolution carried out by means of whole cell microorganisms and commercially available enzymes afforded opposite enantiomerically enriched (-) and (+) isomers of Vince lactam (10), respectively. The effect of compound structures and stereogenic centers on biological activity has been discussed. The highest fungistatic activity was observed for four lactones: 3, 4, 7, and 8 (IC50 = 104.6-115.2 μg/mL) toward B. cinerea AM235. cis-5,6-Epoxy-2-aza[2.2.1]heptan-3-one (13) indicated significant fungistatic activity (IC50 = 107.1 μg/mL) against Aspergillus glaucus AM211. trans-4-Butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and trans-4-butyl-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (7) exhibited high fungistatic activity (IC50 = 143.2 and 110.2 μg/mL, respectively) against P. citrinum AM354 as well.

Straw is a by-product from cereal cultivation. Using straw surplus as a biofuel is a popular means of its management. However, before being used for fuel purposes, straw can be successfully used as a sorbent. The present study investigated the sorption properties of wheat straw (Triticum aestivum L.) modified with ammonia water and epichlorohydrin against the reactive dye Reactive Black 5 (RB5). The tested sorbents were characterized based on FTIR, elemental analysis (C/N content), and pHPZC. The scope of the research included, among others, research on the effect of pH (pH 2–11) on the RB5 sorption efficiency, research on sorption kinetics, and determination of the maximum sorption capacity of the tested sorbents. The sorption efficiency of RB5 on the tested sorbents was the highest at pH 2–3. The experimental data from the research on the sorption kinetics of RB5 were best described by a pseudo-second-order model. The introduction of primary amine groups to the structure of sorbents significantly increased their sorption capacity towards RB5. The obtained sorption capacity of the aminated straw and the aminated straw pre-activated with epichlorohydrin was 24.12 mg RB5/g and 91.04 mg RB5/g, respectively, and it was higher by 44.3% and 444.5% compared to the unmodified straw.

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