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Chemiczna synteza soli amoniowych acetamiprydu, badania spektroskopowe ich równowagowych struktur izomerycznych i ich aktywności grzybobójczej

Maranda Andrzej, Schilf Wojciech, Gucma Mirosław, Gołębiewski Wiesław Marek, Krawczyk Maria, Pucko Wiesław

Przemysł Chemiczny

2023

T. 102, nr 5

438--467

Osiem nieznanych amoniowych soli acetamiprydu (I) (acetamipridium) (chlorowodorek, siarczan, ortofosforan, mrówczan, chlorooctan, trichlorooctan, metanosulfonian i kakodylan) zsyntetyzowano przez wieloetapową konwersję 3-metylopirydyny i zbadano pod kątem struktur równowagowych w solach za pomocą spektroskopii 2D-NMR i widm NOESY w celu wykazania istnienia 2 różnych struktur izomerycznych I (stosunek 80/20). Dla porównania zsyntetyzowano i zidentyfikowano 8 nieznanych analogicznych soli 3-metylopirydyny. Analizę rentgenowską rosnących kryształów I wykorzystano do identyfikacji izomerii geometrycznej cis/trans grup Me w I oraz do potwierdzenia jej struktury. Widma korelacyjne HMBC(¹⁵N-¹H) NMR z powodzeniem wykorzystano do zlokalizowania atomów N w badanych solach I, w których doszło do protonowania. Wykazano również działanie grzybobójcze struktury trans-I.

Eight unknown acetamiprid (I) ammonium (acetamipridium) salts (hydrochloride, sulfate, orthophosphate, formate, chloroacetate, trichloroacetate, methanesulfonate, and cacodilate) were synthesized by multi-stage conversion of 3-methylpyridine and studied for isomeric equil. in solns. by 2D-NMR spectroscopy and NOESY spectra to evidence the existence of 2 different isomeric structures of I (ratio 80/20). For comparison, 8 unknown analogous 3-methylpyridine salts were synthesized and identified. The X-ray anal. of growing I crystals was used to identify the geometric cis/trans isomerism of Me groups in I and to confirm its structure. The HMBC (15N-1H) NMR correlation spectra were successfully used to localize the N atoms in studied I salts where protonation took place. The fungicidal activity of the trans-I structure was also evidenced.

Comparison of the composition and fungicidal activity of essential oils from fennel fruits cultivated in Poland and Egypt

Wodnicka Alicja, Huzar Elżbieta, Dzięcioł Małgorzata, Krawczyk Maria

Polish Journal of Chemical Technology

2019

Vol. 21, nr 2

38--42

The yield, composition and fungicidal activity of essential oils obtained from fennel fruits cultivated in Poland (FEOPOL) and Egypt (FEO-EG) were compared. The influence of the duration of hydrodistillation using a Clevenger apparatus on the essential oil yield was studied. The composition of the fennel essential oils was determined by GC-MS method. Studies have shown that FEO-POL and FEO-EG are two distinct chemotypes, which differ in yield and composition. The fennel fruits cultivated in Poland contained 4.14% of essential oil with trans-anethole as a main component. The plant material from Egypt was characterised by low content of essential oil (1.32%) with a predominant share of estragole. The fungicidal activity was tested in vitro against ten species of pathogenic fungi. The best result for FEO-POL was achieved against Sclerotinia sclerotiorum, Rhizoctonia solani and Botrytis cinerea. Antifungal activity of FEO-EG against tested fungi was weak or none.