紫苏醇酯的合成及除草活性研究

doi:10.3969/j.issn.0253-2417.2019.06.007

林产化学与工业 ›› 2019, Vol. 39 ›› Issue (6): 53-58.doi: 10.3969/j.issn.0253-2417.2019.06.007

紫苏醇酯的合成及除草活性研究

曾小静^1,²,徐士超^1,^2,³,王婧^1,^2,^3,⁴,董欢欢^1,²,陈玉湘^1,^2,³,赵振东^1,^2,^3,*()

1. 中国林业科学研究院林产化学工业研究所; 生物质化学利用国家工程实验室; 国家林业和草原局林产化学工程重点实验室; 江苏省生物质能源与材料重点实验室, 江苏南京 210042
2. 南京林业大学江苏省林业资源高效加工利用协同创新中心, 江苏南京 210037
3. 中国林业科学研究院林业新技术研究所, 北京 100091
4. 北京林业大学材料科学与技术学院, 北京 100083

收稿日期:2019-06-04 出版日期:2019-12-28 发布日期:2019-12-21
通讯作者: 赵振东 E-mail:zdzhao@189.cn
作者简介:曾小静(1995-),女,江西寻乌人,硕士生,主要从事应用化学研究
基金资助:
国家自然科学基金资助项目(31600466);中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2018SZ012)

Synthesis and Herbicidal Activity of Perillyl Esters

Xiaojing ZENG^1,²,Shichao XU^1,^2,³,Jing WANG^1,^2,^3,⁴,Huanhuan DONG^1,²,Yuxiang CHEN^1,^2,³,Zhendong ZHAO^1,^2,^3,*()

1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
3. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
4. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China

Received:2019-06-04 Online:2019-12-28 Published:2019-12-21
Contact: Zhendong ZHAO E-mail:zdzhao@189.cn
Supported by:
国家自然科学基金资助项目(31600466);中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2018SZ012)

摘要/Abstract

摘要：

以紫苏醇为原料，酰氯为酯化试剂，三乙胺作缚酸剂，合成了10种不同结构的紫苏醇酯（2a~2j），得率为50%~90%。通过FT-IR、¹H NMR、¹³C NMR和GC-MS表征了紫苏醇酯类化合物的结构，采用平皿法评价了其对稗草的除草活性。活性评价结果表明：紫苏醇酯对稗草根和茎的生长均有一定抑制作用，其中以紫苏醇正丁酸酯（2i）的除草活性最好，当其浓度为10 mmol/L时对稗草茎和根的生长抑制率分别为90.5%和85.3%，半数抑制浓度（IC₅₀）值分别为1.53和2.48 mmol/L。

关键词: 松节油衍生物, 紫苏醇酯, 稗草, 除草活性

Abstract:

Ten perillyl esters (2a-2j) with different molecular structures were synthesized in the yield of 50%-90% using perillyl alcohol as start material, acid chloride as esterification reagent, triethyla mine as acid binding agent.The structures were characterized by FT-IR, ¹H NMR, ¹³C NMR and GC-MS.The herbicidal activities of them against Echinochloa crusgalli were evaluated by plate method. The results indicated that all synthesized compounds of perillyl ester could inhibite the growth of E.crusgalli. Among them, the herbicidal activity of perillyl alcohol n-butyl ester (2i) showed the best activity against E.crusgalli. The growth inhibition rate against the growth of the stem and root of E.crusgalli was 90.5% and 85.3% at the concentration of 10 mmol/L, and the IC₅₀ values were 1.53 and 2.48 mmol/L, respectively.

Key words: turpentine derivatives, perillyl esters, Echinochloa crusgalli, herbicidal activity

中图分类号:

TQ35

曾小静,徐士超,王婧,董欢欢,陈玉湘,赵振东. 紫苏醇酯的合成及除草活性研究[J]. 林产化学与工业, 2019, 39(6): 53-58.

Xiaojing ZENG,Shichao XU,Jing WANG,Huanhuan DONG,Yuxiang CHEN,Zhendong ZHAO. Synthesis and Herbicidal Activity of Perillyl Esters[J]. Chemistry and Industry of Forest Products, 2019, 39(6): 53-58.

图/表 3

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化合物 compound	不同浓度(mmol/L)时的茎长抑制率/% stem growth inhibition rate of different concentration						不同浓度(mmol/L)时的根长抑制率/% root growth inhibition rate of different concentration
化合物 compound	10	5	2.5	1.25	0.625	0.3125	10	5	2.5	1.25	0.625	0.3125
2a	38.1	30.5	29.8	29.3	28.7	13.6	21.4	3.1	6.9	10.7	8.8	18.6
2b	24.0	22.9	21.5	23.7	19.2	11.4	30.5	28.3	31.1	31.5	25.8	21.9
2c	39.3	32.1	25.4	26.8	29.4	21.0	11.5	5.9	2.8	4.6	7.6	1.4
2d	26.0	27.6	15.6	22.6	16.6	8.6	31.4	12.4	25.8	23.9	11.6	8.1
2e	57.8	33.3	25.4	15.9	21.5	20.2	32.1	44.1	30.5	34.2	17.0	9.7
2f	54.7	45.5	42.7	41.0	38.9	31.6	27.9	15.5	10.4	11.7	13.4	—
2g	24.5	25.7	34.8	20.7	21.9	11.1	17.9	9.8	0.9	7.2	5.1	2.8
2h	35.5	17.4	22.8	9.8	2.7	5.4	41.1	46.4	24.8	42.3	34.1	29.8
2i	90.5	70.2	57.0	27.8	34.3	29.0	85.3	61.5	51.1	41.7	16.8	4.7
2j	74.6	62.3	53.9	43.5	24.8	30.0	47.2	42.9	39.9	26.8	16.1	12.2
莠去津atrazine	100.0	68.0	63.0	39.0	36.0	46.9	100.0	67.7	49.1	42.2	38.5	23.6

化合物 compound	茎stem			根root
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)
2f	y=4.7224+0.3355x	0.9591	6.72	—	—	>10
2i	y=4.7758+1.2233x	0.9191	1.53	y=4.3400+1.6724x	0.9822	2.48
2j	y=4.7352+0.8709x	0.9631	2.01	y=4.2578+0.7874x	0.9735	8.76
莠去津atrazine	y=5.1786+2.7030x	0.7387	0.86	y=4.9761+2.9447x	0.7754	1.02

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紫苏醇酯的合成及除草活性研究

Synthesis and Herbicidal Activity of Perillyl Esters

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