紫苏醇酯的合成及除草活性研究

doi:10.3969/j.issn.0253-2417.2019.06.007

Chemistry and Industry of Forest Products ›› 2019, Vol. 39 ›› Issue (6): 53-58.doi: 10.3969/j.issn.0253-2417.2019.06.007

Previous Articles Next Articles

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)

Abstract

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

CLC Number:

TQ35

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.

Figures/Tables 3

Fig.1

Table 1

Table 2

References 11

1	杨凯, 毛超旭, 陈治希, 等. 薄荷醇酯香料的合成研究进展[J]. 化学通报, 2013, 76 (12): 1091- 1097.
	YANG K , MAO C X , CHEN Z X , et al. Research progress in synthesis of menthol ester spices[J]. Chemistry, 2013, 76 (12): 1091- 1097.
2	范芳, 邓伟杏. 肉桂酸丙酯抑菌活性的研究[J]. 河南农业科学, 2013, 42 (11): 158- 160. doi: 10.3969/j.issn.1004-3268.2013.11.037
	FAN F , DENG W X . Study on antibacterial activity of propyl cinnamate[J]. Journal of Henan Agricultural Sciences, 2013, 42 (11): 158- 160. doi: 10.3969/j.issn.1004-3268.2013.11.037
3	骆焱平, 李元祥, 赵培亮, 等. 甲氧丙烯酸酯类杀菌剂的研究进展[J]. 中国科技论文, 2006, 1 (1): 20- 26. doi: 10.3969/j.issn.2095-2783.2006.01.003
	LUO Y P , LI Y X , ZHAO P L , et al. Research progress on the fungicidal strobilurin derivatives[J]. Sciencepaper Online, 2006, 1 (1): 20- 26. doi: 10.3969/j.issn.2095-2783.2006.01.003
4	袁鹏涛. 高杀虫活性的多烯环丙烷羧酸酯类化合物[J]. 世界农药, 2015, 37 (5): 15- 21, 39.
	YUAN P T . High insecticidal activity of the polyene cyclopropanecarboxylic acid ester compounds[J]. World Pesticides, 2015, 37 (5): 15- 21, 39.
5	包文娟. 芳氧苯氧羧酸类旋光性除草剂的研究进展[J]. 今日农药, 2007, 37 (12): 36- 38.
	BAO W J . Progress on aryloxyphenoxy carboxylate acid herbicide with optical activity[J]. Fine Chemical Intermediates, 2007, 37 (12): 36- 38.
6	郑辉, 刘运奎, 赵卿, 等. 含氟吡啶羧酸酯类化合物的合成及生物活性[J]. 应用化学, 2010, 27 (2): 164- 168.
	ZHENG H , LIU Y K , ZHAO Q , et al. Synthesis and biological activity of fluorine-substituted pyridine-heterocyclic carboxylate compounds[J]. Chinese Journal of Applied Chemistry, 2010, 27 (2): 164- 168.
7	冯程程, 马红. 除草剂应用现状及挑战[J]. 江苏农业科学, 2014, 42 (8): 111- 113. doi: 10.3969/j.issn.1002-1302.2014.08.039
	FENG C C , MA H . Herbicides application status and challenges[J]. Jiangsu Agricultural Sciences, 2014, 42 (8): 111- 113. doi: 10.3969/j.issn.1002-1302.2014.08.039
8	施娟娟, 马亚芳, 倪珏萍. 2, 4-滴类药剂防除麦田阔叶杂草的初步研究[J]. 现代农药, 2012, 11 (1): 50- 53.
	SHI J J , MA Y F , NI J P . Preli minary study on 2, 4-D reagent in chemical control broadleaf weedsin wheat field[J]. Modern Agrochemicals, 2012, 11 (1): 50- 53.
9	温广月, 钱振官, 李涛, 等. 氰氟草酯使用技术对双穗雀稗防除效果的影响[J]. 植物保护, 2017, (5): 210- 214. doi: 10.3969/j.issn.0529-1542.2017.05.035
	WEN G Y , QIAN Z G , LI T , et al. Effect of application technology of cyhalofop-butyl on Paspalum distichum control[J]. Plant Protection, 2017, (5): 210- 214. doi: 10.3969/j.issn.0529-1542.2017.05.035
10	文马强, 周小毛, 刘佳, 等. 直播水稻田千金子对氰氟草酯抗性测定及抗性生化机理研究[J]. 南方农业学报, 2017, (4): 647- 652. doi: 10.3969/j.issn.2095-1191.2017.04.013
	WEN M Q , ZHOU X M , LIU J , et al. Resistance of Leptochloa chinensis(L) Nees.to cyhalofop-butyl in rice field of direct seeding and resistance biochemical mechanism research[J]. Journal of Southern Agriculture, 2017, (4): 647- 652. doi: 10.3969/j.issn.2095-1191.2017.04.013
11	刘学, 顾宝根. 农药生物活性测试标准操作规范:除草剂卷[M]. 北京: 化学工业出版社, 2016: 120- 121.
	LIU X , GU B G . Standard Practice for Pesticide Bioactivity Testing:Herbicide Roll[M]. Beijing: Chemical Industry Press, 2016: 120- 121.

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

[1]	ZHENG Wanli, MA Xianli, ZHOU Xiaoqun, LI Fangyao, XIN Mao, JIANG Caina. Synthesis, Antibacterial and Herbicidal Evaluation of Camphoric Acid-based Acylhydrazone Compounds [J]. Chemistry and Industry of Forest Products, 2019, 39(5): 41-49.
[2]	Xiaojiang MA,Jin WANG,Feng TANG,Quan GAO,Wei LIU,Li SONG. Optimization of Vacuum Extraction of Total Saponins from Sapindus mukorossi Gaertn and Its Herbicidal Activity [J]. Chemistry and Industry of Forest Products, 2019, 39(1): 108-114.
[3]	MA Yuan, DUAN Wengui, LIN Guishan, LIU Luzhi, HUANG Zhengsong, LEI Fuhou. Synthesis and Biological Activities of Perillaldehyde-based Schiff Base-(thio) urea Compounds [J]. Chemistry and Industry of Forest Products, 2017, 37(1): 54-62.
[4]	DUAN Wen-gui;DUAN Wen-gui;LI Xing-ren;MA Xian-li;MO Qi-jin;XU Xue-tang. Synthesis and Herbicidal Activity of 5-Dehydroabietyl- 1,3,4-thiadiazole Derivatives [J]. , 2011, 31(1): 1-8.
[5]	BI Liang-wu;ZHAO Zhen-dong;LI Dong-mei;WANG Jing;GU Yan. STUDY ON ETHYNYLATION OF TERPENYLACETONES UNDER NORMAL PRESSURE [J]. , 2005, 25(04): 1-5.

Synthesis and Herbicidal Activity of Perillyl Esters

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 3

References 11

Related Articles 5

Recommended Articles

Metrics

Comments