四氢芳樟基酰胺类化合物的合成及除草活性研究

doi:10.3969/j.issn.0253-2417.2023.03.011

林产化学与工业 ›› 2023, Vol. 43 ›› Issue (3): 89-100.doi: 10.3969/j.issn.0253-2417.2023.03.011

四氢芳樟基酰胺类化合物的合成及除草活性研究

张红梅¹^,², 王婧¹^,², 陈玉湘¹, 徐士超¹, 蒋建新², 赵振东¹^,*()

1. 中国林业科学研究院林产化学工业研究所；江苏省生物质能源与材料重点实验室；国家林业和草原局林产化学工程重点实验室；林木生物质低碳高效利用国家工程研究中心；江苏省林业资源高效加工利用协同创新中心，江苏南京 210042
2. 北京林业大学材料科学与技术学院，北京 100083

收稿日期:2022-01-11 出版日期:2023-06-28 发布日期:2023-06-27
通讯作者: 赵振东 E-mail:zdzhao@189.cn
作者简介:赵振东，研究员，博士生导师，研究领域为萜类化学、松树病虫害化学、天然产物化学、应用化学等；E-mail：zdzhao@189.cn
张红梅(1992—)，女，云南红河人，博士生，主要从事萜类化学转化利用等方面的研究
基金资助:
国家自然科学基金资助项目(31870557)

Synthesis and Herbicidal Activity of Tetrahydrolinalyl Amides

Hongmei ZHANG¹^,², Jing WANG¹^,², Yuxiang CHEN¹, Shichao XU¹, Jianxin JIANG², Zhendong ZHAO¹^,*()

1. Institute of Chemical Industry of Forest Products, CAF; Key Lab. of Biomass Energy and Material, Jiangsu Province; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing 210042, China
2. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China

Received:2022-01-11 Online:2023-06-28 Published:2023-06-27
Contact: Zhendong ZHAO E-mail:zdzhao@189.cn

摘要/Abstract

摘要：

以四氢芳樟醇为原料，设计合成了17种四氢芳樟基酰胺类化合物(2, 4a~4p)，得率64.8%~96.9%。通过FT-IR、¹H NMR、¹³C NMR和HRMS表征了系列化合物的结构，并评价了目标化合物对黑麦草和稗草的除草活性。研究结果表明：四氢芳樟基酰胺类化合物对黑麦草和稗草均有一定的生长抑制活性，化合物2、4a、4o对黑麦草的萌芽前(芽前)除草活性最好，对黑麦草根长的半数抑制浓度(IC₅₀)值分别为0.05、0.05和0.03 mmol/L(稍差于阳性对照草甘膦)，对黑麦草茎长的IC₅₀值分别为0.06、0.05和0.05 mmol/L(优于草甘膦)。化合物4b对稗草根长和茎长的IC₅₀值分别为0.06和0.15 mmol/L(与草甘膦相同)。构效关系分析表明：四氢芳樟基酰胺类化合物在不同杂草间具有选择性；含烷基取代的化合物除草活性强于含苯环和呋喃环的，苯环上含给电子基团时活性强于含吸电子基团的，且给电子基团位于苯环邻位和间位时除草活性更好。

关键词: 四氢芳樟醇, 四氢芳樟胺, 酰胺类化合物, 除草活性

Abstract:

Seventeen tetrahydrolinalyl amides(2, 4a-4p) were designed and synthesized using tetrahydrolinalool as starting material. Their structures were characterized by FT-IR, ¹H NMR, ¹³C NMR and HRMS, then the herbicidal activities against Lolium perenne and Echinochloa crusgalli were evaluated. The results showed that the tetrahydrolinalyl amides exhibited certain growth inhibitory effects on L. perenne and E. crusgalli. Compounds 2, 4a, 4o showed the best pre-emergence herbicidal activity against L. perenne, where the inhibitory concentration 50%(IC₅₀) values for the root growth of L. perenne were 0.05, 0.05, and 0.04 mmol/L, respectively(weaker than that of the positive control glyphosate), and the IC₅₀ values for the shoot of L. perenne were 0.06, 0.05, and 0.05 mmol/L, respectively(stronger than that of glyphosate). The IC₅₀ values of compound 4b on root and shoot growth of E. crusgalli were 0.06 and 0.15 mmol/L(equal to that of glyphosate), respectively. The structure-activity relationship analysis showed that tetrahydrolinayl amides exhibited selectivity among different weed species. The compounds containing alkyl group showed higher herbicidal activity than that of benzene ring and furan ring. The herbicidal activity of compounds with electron-donating group on benzene ring was stronger than that with electron-withdrawing group, exhibiting better activity when it was located at the ortho- and meta-position of benzene ring.

Key words: tetrahydrolinalool, tetrahydrolinalyl amine, amides, herbicidal activity

中图分类号:

TQ35

张红梅, 王婧, 陈玉湘, 徐士超, 蒋建新, 赵振东. 四氢芳樟基酰胺类化合物的合成及除草活性研究[J]. 林产化学与工业, 2023, 43(3): 89-100.

Hongmei ZHANG, Jing WANG, Yuxiang CHEN, Shichao XU, Jianxin JIANG, Zhendong ZHAO. Synthesis and Herbicidal Activity of Tetrahydrolinalyl Amides[J]. Chemistry and Industry of Forest Products, 2023, 43(3): 89-100.

图/表 5

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化合物compound	不同浓度(mmol?L^-1)下的根长抑制率/% root growth inhibition rate at different concentration							不同浓度(mmol?L^-1)下的茎长抑制率/% shoot growth inhibition rate at different concentration
化合物compound	2.5	1.25	0.625	0.313	0.156	0.078	0.039	2.5	1.25	0.625	0.313	0.156	0.078	0.039
1	80.4	55.5	47.3	35.8	31.1	26.4	19.0	82.6	62.9	50.9	37.7	30.2	20.8	17.6
2	100.0	100.0	94.7	89.4	65.7	54.6	49.4	100.0	100.0	97.1	92.3	70.0	55.4	46.5
3	100.0	100.0	99.5	71.0	55.9	37.8	30.8	100.0	100.0	87.2	58.4	47.8	36.4	28.7
4a	97.9	96.3	91.2	82.0	72.4	58.1	43.4	100.0	96.7	93.6	86.5	76.2	58.7	47.5
4b	94.1	90.1	84.7	75.5	76.3	63.7	47.0	94.7	90.0	89.1	75.2	68.5	55.9	34.0
4c	92.3	81.3	70.6	58.3	46.5	38.9	32.2	93.9	79.1	72.9	61.3	48.5	42.3	31.0
4d	82.3	69.0	62.2	55.1	50.1	38.2	29.4	84.6	73.0	66.2	56.8	53.5	41.2	29.8
4e	100.0	98.1	89.5	62.5	46.6	31.8	25.2	100.0	98.5	89.2	67.2	52.0	49.0	42.2
4f	89.0	67.5	50.1	48.9	42.4	35.4	36.1	90.5	65.1	51.9	52.7	47.8	42.4	38.5
4g	98.9	98.5	84.7	69.3	62.1	48.2	44.4	98.8	98.0	88.0	72.0	65.9	52.5	47.5
4h	66.6	55.5	53.8	45.8	36.9	32.5	21.6	69.4	51.8	50.7	41.6	32.6	27.4	20.8
4i	75.1	65.6	58.2	40.5	35.9	30.2	27.6	76.9	67.2	57.2	39.9	37.7	24.9	19.5
4j	69.7	65.8	59.4	56.4	48.9	43.1	26.2	73.1	66.3	61.8	56.1	47.1	40.2	18.7
4k	48.6	38.3	35.5	28.9	21.8	15.2	6.7	55.8	43.0	42.3	39.4	30.3	21.5	8.5
4l	84.5	74.7	55.6	49.9	39.2	25.2	15.3	90.3	79.8	60.5	53.7	45.3	31.1	22.0
4m	69.6	60.2	43.2	34.3	32.6	22.9	19.3	71.8	61.4	50.8	38.5	33.1	25.2	19.8
4n	83.7	69.2	55.4	44.9	32.2	25.9	19.1	94.0	83.7	77.3	67.1	54.4	43.5	33.3
4o	94.4	85.1	79.5	73.8	68.2	63.9	56.8	95.0	84.2	76.0	68.6	62.3	58.1	52.2
4p	67.9	53.6	45.5	43.5	35.6	26.9	20.8	65.6	61.8	53.6	50.6	49.9	43.0	34.3
草甘膦glyphosate	100.0	100.0	95.7	87.8	76.1	68.6	57.8	100.0	99.5	93.6	82.3	55.0	40.2	37.8

化合物compound	不同浓度(mmol?L^-1)下的根长抑制率/% root growth inhibition rate at different concentration						不同浓度(mmol?L^-1)下的茎长抑制率/% shoot growth inhibition rate at different concentration
化合物compound	2.5	1.25	0.625	0.313	0.156	0.078	2.5	1.25	0.625	0.313	0.156	0.078
1	29.4	26.9	23.8	23.8	17.9	9.8	11.6	9.8	9.3	5.2	2.2	0
2	100.0	90.0	76.5	49.2	31.6	21.5	87.0	56.8	36.4	25.9	22.6	20.8
3	100.0	99.4	91.0	57.4	27.2	19.4	100.0	94.8	77.5	38.2	16.3	13.5
4a	77.8	74.0	68.6	56.1	48.3	33.8	59.5	58.0	51.3	44.3	33.6	23.6
4b	84.0	78.2	74.7	65.0	62.4	51.6	72.5	69.0	63.8	57.2	50.1	43.9
4c	52.8	43.9	35.2	33.3	28.8	22.0	41.0	29.2	26.0	15.3	16.4	10.4
4d	56.3	46.3	39.8	32.9	30.4	27.6	48.3	37.1	34.4	28.0	22.4	20.5
4e	58.7	51.3	45.7	31.8	27.4	22.9	48.2	41.5	38.2	23.5	14.0	11.1
4f	49.2	28.7	27.0	23.7	17.1	13.4	31.0	17.4	11.8	11.2	13.1	8.4
4g	37.6	31.1	28.8	24.6	19.6	13.2	34.5	29.5	26.8	18.9	12.6	6.7
4h	35.3	28.5	26.3	24.3	19.1	9.2	25.4	23.5	17.4	17.3	13.3	5.9
4i	46.3	40.5	39.8	30.8	24.2	19.2	42.1	35.5	33.2	29.2	22.9	18.9
4j	65.9	58.2	55.0	48.5	45.1	39.4	58.0	48.6	45.4	38.8	33.9	29.6
4k	46.6	36.7	25.8	21.0	17.3	11.1	38.3	29.9	26.8	24.9	15.3	10.7
4l	47.8	46.6	39.3	32.1	29.9	27.3	39.4	32.2	30.0	27.8	22.2	19.9
4m	28.5	24.2	17.0	12.0	12.5	6.7	25.7	19.0	9.9	9.0	5.3	6.9
4n	57.4	53.2	48.2	42.0	39.7	26.5	42.5	40.7	34.2	26.5	27.1	18.4
4o	77.6	75.7	66.3	59.4	57.7	53.5	51.9	54.0	48.7	41.6	36.8	29.5
4p	42.0	35.3	32.6	25.8	26.8	24.0	36.2	25.2	20.0	18.6	21.4	17.5
草甘膦glyphosate	100.0	99.8	92.3	83.9	79.6	69.5	97.5	91.9	77.2	64.0	54.1	38.5

化合物compound	根root			茎shoot
化合物compound	毒力回归方程toxicity regression equations	R	IC₅₀/(mmol?L^-1)	毒力回归方程toxicity regression equations	R	IC₅₀/(mmol?L^-1)
1	y=5.223 8+0.850 1x	0.956 4	0.55	y=5.321 8+1.000 6x	0.979 4	0.48
2	y=6.851 0+1.460 1x	0.964 4	0.05	y=7.186 5+1.746 3x	0.977 0	0.06
3	y=7.372 8+2.331 6x	0.899 0	0.10	y=6.136 0+1.314 2x	0.946 8	0.14
4a	y=6.590 8+1.248 3x	0.998 6	0.05	y=6.747 8+1.310 0x	0.998 0	0.05
4b	y=6.243 7+0.856 4x	0.983 1	0.04	y=6.263 9+1.080 0x	0.985 3	0.07
4c	y=5.836 6+1.024 4x	0.984 4	0.15	y=5.887 1+1.042 0x	0.978 8	0.14
4d	y=5.524 0+0.748 2x	0.988 9	0.20	y=5.620 9+0.788 9x	0.990 1	0.16
4e	y=6.604 4+1.831 8x	0.967 9	0.13	y=6.610 2+1.520 2x	0.931 7	0.09
4f	y=5.500 2+0.782 6x	0.895 7	0.23	y=5.546 0+0.720 3x	0.862 8	0.17
4g	y=6.618 5+1.475 8x	0.956 6	0.08	y=6.627 1+1.388 9x	0.969 0	0.07
4h	y=5.169 8+0.623 8x	0.988 4	0.53	y=5.127 6+0.678 9x	0.984 7	0.65
4i	y=5.311 9+0.738 6x	0.977 8	0.38	y=5.344 8+0.892 9x	0.992 2	0.41
4j	y=5.361 9+0.579 7x	0.963 8	0.24	y=5.413 1+0.738 6x	0.955 5	0.28
4k	y=4.722 7+0.742 4x	0.976 2	2.36	y=4.912 7+0.723 9x	0.942 1	1.32
4l	y=5.530 2+1.091 3x	0.993 8	0.33	y=5.713 0+1.097 7x	0.986 7	0.22
4m	y=5.118 5+0.761 7x	0.980 3	0.70	y=5.204 3+0.789 0x	0.994 6	0.55
4n	y=5.437 0+1.004 1x	0.989 5	0.37	y=5.995 9+1.056 4x	0.993 2	0.11
4o	y=6.085 4+0.708 8x	0.964 5	0.03	y=6.035 2+0.801 8x	0.950 0	0.05
4p	y=5.112 7+0.652 9x	0.986 7	0.67	y=5.239 6+0.410 9x	0.978 8	0.26
草甘膦glyphosate	y=6.851 0+1.236 0x	0.983 7	0.03	y=7.043 8+1.949 9x	0.965 3	0.09

化合物compound	根root			茎shoot
化合物compound	毒力回归方程toxicity regression equations	R	IC₅₀/(mmol?L^-1)	毒力回归方程toxicity regression quations	R	IC₅₀/(mmol?L^-1)
1	y=4.357 9+0.442 9x	0.913 1	28.17	y=3.643 5+0.654 6x	0.932 2	118.13
2	y=6.039 7+1.775 8x	0.989 6	0.26	y=5.219 4+1.211 8x	0.912 2	0.66
3	y=6.973 5+2.889 5x	0.976 4	0.21	y=6.206 6+2.390 2x	0.971 5	0.31
4a	y=5.544 0+0.788 3x	0.985 3	0.20	y=5.095 4+0.650 2x	0.973 7	0.71
4b	y=5.746 8+0.611 3x	0.991 6	0.06	y=5.428 2+0.513 3x	0.996 6	0.15
4c	y=4.813 4+0.520 2x	0.985 2	2.28	y=4.450 0+0.648 2x	0.971 5	7.05
4d	y=4.884 9+0.494 6x	0.976 3	1.71	y=4.691 1+0.510 3x	0.984 3	4.03
4e	y=4.959 5+0.671 5x	0.989 1	1.15	y=4.702 2+0.844 7x	0.980 1	2.25
4f	y=4.564 2+0.636 4x	0.951 8	4.84	y=4.112 2+0.474 0x	0.863 2	74.63
4g	y=4.504 4+0.495 6x	0.982 4	10.00	y=4.408 1+0.719 5x	0.975 6	6.65
4h	y=4.446 6+0.544 6x	0.934 6	10.38	y=4.201 0+0.539 1x	0.934 6	30.34
4i	y=4.741 5+0.522 9x	0.981 8	3.12	y=4.626 5+0.439 9x	0.991 2	7.06
4j	y=5.205 2+0.431 6x	0.993 7	0.33	y=4.970 8+0.474 4x	0.992 8	1.15
4k	y=4.583 2+0.725 5x	0.992 3	3.75	y=4.479 9+0.595 4x	0.974 3	7.48
4l	y=4.808 8+0.404 5x	0.979 0	2.97	y=4.554 0+0.366 0x	0.986 0	16.55
4m	y=4.201 9+0.590 8x	0.976 8	22.44	y=4.006 5+0.609 6x	0.928 2	42.65
4n	y=5.032 0+0.498 7x	0.968 2	0.86	y=4.670 0+0.465 1x	0.971 0	5.12
4o	y=5.569 1+0.478 8x	0.974 0	0.06	y=4.986 8+0.420 0x	0.958 0	1.07
4p	y=4.613 2+0.335 7x	0.961 4	14.20	y=4.365 0+0.316 2x	0.832 5	101.89
草甘膦glyphosate	y=7.221 4+1.772 0x	0.908 7	0.06	y=6.235 0+1.474 5x	0.987 7	0.15

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Synthesis and Herbicidal Activity of Tetrahydrolinalyl Amides

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