vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2022-12-1-8-14vuzbiochemi-748Research ArticleХИМИЧЕСКИЕ НАУКИCHEMICAL SCIENCESСинтез и биологические испытания на пестицидную активность 8-азастероидовSynthesis and biological testing for pesticidal activity of 8-azasteroidshttps://orcid.org/0000-0002-5838-1681ПыркоА. Н.PyrkoA. N.

А. Н. Пырко, к.х.н., доцент кафедры экологической химии и биохимии

220070, г. Минск, ул. Долгобродская, 23/1,

Anatoly N. Pyrko, Cand. Sci. (Chemistry), Associate Professor,Department of Environmental Chemistry and Biochemistry

23, Dolgobrodskaya St., Minsk, 220070, Belarus,

pyrko@yandex.ruМеждународный государственный экологический институт имени А. Д. Сахарова Белорусского государственного университетаБеларусьInternational Sakharov Environmental Institute of Belarusian State UniversityBelarus202201042022121814Copyright © Пырко А.Н., 20222022Пырко А.Н.Pyrko A.N.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/748

Целью данного исследования является синтез и тестирование на пестицидную активность 2,3-диметокси-16,16-диметил-D-гомо-8-азагона-1,3,5(10),13-тетраен-12,17а-диона и гидрохлорида 2,3-диметокси-16,16-диметил-D-гомо-8-азагона-1,3,5(10),13-тетраен-12-имино-17а-она, которые могли бы стать основой средств защиты растений. Первое соединение было получено конденсацией 6,7-диметокси-2,3-дигидроизохинолина с 2-ацетил-5,5-диметилциклогексан-1,3-дионом. Второе – взаимодействием первого с хлористым аммонием. 2-Ацетил-5,5-диметилциклогексан-1,3- дион был получен нагреванием димедона с уксусной кислотой в полифосфорной кислоте. 6,7- Диметокси-2,3-дигидроизохинолин был синтезирован в две стадии. Кипячением 2-(3,5-диметоксифенил)этиламина в муравьиной кислоте получали соответствующий амид, циклизацию которого проводили в присутствии хлорокиси фосфора. Структура полученных соединений подтверждена данными ИК, 1Н ЯМР, УФ-спектров и элементного анализа. В ИК-спектрах поглощения 2,3-диметокси-16,16-диметил-D-гомо-8-азагона-1,3,5(10),13-тетраен-12,17а-диона и гидрохлорида 2,3- диметокси-16,16-диметил-D-гомо-8-азагона-1,3,5(10),13-тетраен-12-имино-17а-она присутствуют полосы енаминодикетонной (1535, 1580, 1615, 1625, 1670 см-1 ) и ениминокетонной (1595, 1650, 3260 см-1 ) групп соответственно. В их УФ-спектрах поглощения, записанных в этаноле, имеются две полосы поглощения (265,303 и 268,317 нм), соответствующие ππ*-переходам тех же фрагментов молекул. В масс-спектрах двух полученных тетрациклов присутствуют пики молекулярных ионов. 1Н ЯМР-спектры соответствуют структурам всех полученных соединений. Синтезированные соединения были испытаны на некоторых видах инсектицидной (против Toxoptera graminum, Musca domestica, Meloidogyne incognita, Heliothis virescens, Diabrotica undecimpunctata howardi, Caenorhabditis elegans), фунгицидной (против Drechslera, Erysiphe, Puccinia, Peronospora) и гербицидной активности (против Amaranthus retroflexus, Brassica rapa, Abutilon theophrasti, Alopecurus myosuroides, Avena fatua, Echinochloa crusgalli). Оба синтезированные соединения показали гербицидную активность против Amaranthus retroflexus, Brassica rapa, Abutilon theophrasti и инсектицидную против Toxoptera graminum. Гидрохлорид 2,3-диметокси-16,16-диметил-D-гомо-8-азагона1,3,5(10),13-тетраен-12-имино-17а-онa проявил инсектицидную активность против Musca domestica и фунгицидную против Drechslera.

The aim of the present study is the synthesis and testing for pesticidal activities of 2,3-dimethoxy16,16-dimethyl-D-homo-8-azagona-1,3,5(10),13-tetraene-12,17а-one and 2,3-dimethoxy-16,16-dimethyl-dhomo-8-azagona-1,3,5(10),13-tetraene-12-imino-17а-one hydrochloride which could become the basis the basis of plant protection products. The first compound was obtained by condensation of 6,7-dimethoxy-2,3- dihydroisoquinoline with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione. The second substance was synthesized by interaction of the first with ammonium chloride. 2-Acetyl-5,5-dimethylcyclohexane-1,3-dione was prepared by heating dimedone with acetic acid in polyphosphoric acid. 6,7-Dimethoxy-2,3-dihydroisoquinoline was synthesized in two steps. Boiling 2-(3,5-dimethoxyphenyl)ethylamine in formic acid gave the corresponding amide, which was cyclized in the presence of phosphorus oxychloride. The structure of the obtained compounds is confirmed by the data of IR, 1H NMR, UV spectra and elemental analysis. In the IR absorption spectra of 2,3-dimethoxy-16,16-dimethyl-D-homo-8-azagona-1,3,5(10),13-tetraene-12,17a-dione and 2,3-dimethoxy-16,16-dimethyl-D-homo-8-azagona-1,3,5(10),13-tetraen-12-imino-17a-one hydrochloride, enaminodiketone bands are present (1535, 1580, 1615, 1625, 1670 cm-1 ) and enimine ketone (1595, 1650, 3260 cm-1 ) groups, respectively. Their UV absorption spectra recorded in ethanol contain two absorption bands (265.303 and 268.317 nm) corresponding to ππ* transitions of the same molecular fragments. The mass spectra of the two obtained tetracycles contain peaks of molecular ions. 1H NMR spectra correspond to the structures of all obtained compounds The synthesized compounds were tested for certain types of insecticide (against Toxoptera graminum, Musca domestica, Meloidogyne incognita, Heliothis virescens, Diabrotica undecimpunctata howardi, Caenorhabditis elegans), fungicidal (against Drechslera, Erysiphe, Puccinia, Peronospora) and herbicidal (against Amaranthus retroflexus, Brassica rapa, Abutilon theophrasti, Alopecurus myosuroides, Avena fatua, Echinochloa crus galli) activities. Both synthesized compounds showed herbicidal activity against Amaranthus retroflexus, Brassica rapa, Abutilon theophrasti and insecticidal activity against Toxoptera graminum. Hydrochloride 2,3-dimethoxy-16,16-dimethyl-D-homo-8-azagon-1,3,5(10),13- tetraene-12-imino-17a-one showed insecticidal activity against Musca domestica and fungicidal activity against Drechslera.

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The authors declare that there are no conflicts of interest present.