8-偶氮小行星的合成及杀虫活性的生物学检测

A. N. Pyrko
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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. 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引用次数: 0

摘要

本研究的目的是合成2,3-二甲氧基16,16-二甲基-d -同型-8-阿扎哥拿-1,3,5(10),13-四甲基-12,17 -1和2,3-二甲氧基-16,16-二甲基-多型-8-阿扎哥拿-1,3,5(10),13-四甲基-12-亚胺-17 -1盐化物,并进行杀虫活性测试,为植物保护产品的开发奠定基础。第一个化合物由6,7-二甲氧基-2,3-二氢异喹啉与2-乙酰-5,5-二甲基环己烷-1,3-二酮缩合而得。第二种物质是由第一种物质与氯化铵相互作用合成的。以二美酮为原料,在多磷酸中以乙酸加热制备了2-乙酰-5,5-二甲基环己烷-1,3-二酮。6,7-二甲氧基-2,3-二氢异喹啉分两步合成。在甲酸中煮沸2-(3,5-二甲氧基苯基)乙胺,得到相应的酰胺,在氯氧磷存在下环化。所得化合物的结构经红外光谱、核磁共振氢谱、紫外光谱和元素分析证实。在2,3-二甲氧基-16,16-二甲基-d -同-8-氮杂根-1,3,5(10),13-四烯-12,17a-二酮和2,3-二甲氧基-16,16-二甲基-d -同-8-氮杂根-1,3,5(10),13-四烯-12-亚胺-17a- 1盐酸的红外吸收光谱中,胺基二酮分别存在(1535,1580,1615,1625,1670 cm-1)和亚胺酮(1595,1650,3260 cm-1)基团。它们在乙醇中的紫外吸收光谱包含两个吸收带(265.303和268.317 nm),对应于同一分子片段的π*跃迁。得到的两个四环的质谱包含分子离子峰。合成的化合物对某些类型的杀虫剂(对禾形弓形虫、家蝇、黑线蛾、绿萝蛾、非impunctata howardi、秀丽隐隐线虫)、杀菌剂(对Drechslera、erysiphhe、Puccinia、Peronospora)和除草剂(对逆花苋、油菜、Abutilon theophrasti、Alopecurus myosuides、Avena fatua、棘爪动物活动。两种化合物均具有对逆转录苋、油菜、苘麻的除草活性和对禾状弓形虫的杀虫活性。盐酸2,3-二甲氧基-16,16-二甲基-d -同型-8-氮杂龙-1,3,5(10),13-四烯-12-亚胺-17a- 1对家蝇有杀虫活性,对锥虫有杀真菌活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis and biological testing for pesticidal activity of 8-azasteroids
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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