CN106565469A - 4-羟基-3-甲氧基肉桂酸乙酯的高效除草活性 - Google Patents

4-羟基-3-甲氧基肉桂酸乙酯的高效除草活性 Download PDF

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CN106565469A
CN106565469A CN201510645642.1A CN201510645642A CN106565469A CN 106565469 A CN106565469 A CN 106565469A CN 201510645642 A CN201510645642 A CN 201510645642A CN 106565469 A CN106565469 A CN 106565469A
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ferulic acid
ethyl ester
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杨鹏
张利辉
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

本发明公开一种具有除草活性的物质4-羟基-3-甲氧基肉桂酸乙酯，其高效的除草活性，属于人工合成化学品应用于农业植物保护领域。此物质对马唐、反枝苋、稗草、狗尾草、虎尾草等杂草均有一定的抑制效果，其中对杂草马唐的抑制效果最佳，IC50为281.53mg·L-1，具有安全环保，对非靶标作物无害等优点。

Description

4-羟基-3-甲氧基肉桂酸乙酯的高效除草活性
技术领域
本发明公布一种人工合成4-羟基-3-甲氧基肉桂酸乙酯的合成方法及其用于防控农业杂草的方法，属于人工合成化学品应用于农业植物保护领域。
背景技术
全世界约有3万余种杂草，其中1800多种能够对各种农业作物造成危害，每年会造成作物总产量约9.7％的损失。常规化学除草剂是目前常用的防治杂草的方法，但长期使用，其弊端也日益突出，如杂草产生抗药性、水体土壤污染、残留不易降解等。开发研制无污染、安全的新型除草剂已成为当务之急。生物源除草剂因其具有对非靶标植物影响小、环境负效应小、安全性高的特点而备受人们的青睐。微生物次生代谢产物除草剂具有结构新颖、多靶标作用位点、环境中易于降解等优点。阿魏酸为一种广泛存在的植物及微生物次生代谢物质，本专利报道的内容是利用阿魏酸为基本骨架对其进行结构改造，扩大了阿魏酸分子本身的除草谱，提高了其除草活性、对非靶标生物的安全性。
阿魏酸分子中的烷烃较短且含有双键，亲水性较强，难以深入到生物膜脂质双分子层中发挥其活性作用，故对阿魏酸分子进行结构改造的研究引起了人们极大的兴趣[6-7]。阿魏酸与香豆素相连接，保持并增加了两母体化合物的抗血栓活性；以阿魏酸为先导物，用二甲氨基、哌啶基和吗啉基替代咪唑基，设计合成的阿魏酸衍生物具有更强的抗血小板凝集活性；向分子中引入具有杀菌、抗病毒活性的苯并呋喃、烷氧基、苯并恶唑等结构基团，所得到的阿魏酸衍生物可用于防治烟草花叶病毒、辣椒病毒、番茄病毒、甘薯病毒、马铃薯病毒和瓜类病毒及玉米矮花叶病毒等。目前从4-羟基-3-甲氧基肉桂酸乙酯作为新型除草剂的报道还未出现。通过检索，也尚未发现以4-羟基-3-甲氧基肉桂酸乙酯做除草剂的相关文献报道。
本发明公开4-羟基-3-甲氧基肉桂酸乙酯的简单合成和高效除草活性，属于微生物次生代谢产物结构改造应用于农业植物保护领域。4-羟基-3-甲氧基肉桂酸乙酯对马唐、反枝苋、稗草、狗尾草、虎尾草等杂草均有一定的抑制效果，尤其是对杂草马唐的抑制效果最佳，IC50为281.53mg·L-1，具有安全，环保，对非靶标作物无害等优点。
权利要求
1、一种化学药品，4-羟基-3-甲氧基肉桂酸乙酯的合成及高效除草活性；
2、权利要求1所述4-羟基-3-甲氧基肉桂酸乙酯，其特征在于：此物质合成方便，易于纯化，对马唐、反枝苋、稗草、狗尾草、虎尾草等杂草的生长均有优秀的除草活性；
3、权利要求1所述的4-羟基-3-甲氧基肉桂酸乙酯的制备方法；
4、权利要求1所述的4-羟基-3-甲氧基肉桂酸乙酯的除草活性
发明内容
一、4-羟基-3-甲氧基肉桂酸乙酯的除草活性
4-羟基-3-甲氧基肉桂酸乙酯对马唐、反枝苋、稗草、狗尾草、虎尾草、苋菜等杂草均有一定的抑制效果，相同浓度的4-羟基-3-甲氧基肉桂酸乙酯施用于玉米、小麦、大豆、高粱植株均未见明显药害。4-羟基-3-甲氧基肉桂酸乙酯具体除草效果见具体实施方式。
二、4-羟基-3-甲氧基肉桂酸乙酯的制备及纯化方法
反应体系：阿魏酸--30g；无水乙醇--500g；浓硫酸--1.0ml；搅拌反应，
反应温度：85℃；反应时间：5h
4-羟基-3-甲氧基肉桂酸乙酯合成产品的纯化：反应体系中加入等体积的饱和NaHCO3震荡后，加入等体积的乙酸乙酯萃取。萃取后用无水Na2SO4将乙酸乙酯中的水分吸收除去，将乙酸乙酯及无水乙醇的混合物40℃下旋蒸干净既得到4-羟基-3-甲氧基肉桂酸乙酯粗品。4-羟基-3-甲氧基肉桂酸乙酯粗品过200目硅胶层析柱回收4-羟基-3-甲氧基肉桂酸乙酯组分，将洗脱剂旋蒸干净既得白色4-羟基-3-甲氧基肉桂酸乙酯纯品，其纯度可≥99％。
具体实施方式
实例1：
以马唐、马齿苋、播娘蒿为测试杂草，设1000、500、250、125、62.5、0mg/kg 6个浓度，以甲醇∶丙酮＝4∶1(v/v)为溶剂将4-羟基-3-甲氧基肉桂酸乙酯配制到相应的浓度。在50mL烧杯中垫玻璃棒，铺2层滤纸，以1000μL配置好的药剂润湿滤纸，40℃下烘干60min，将溶剂挥发干净，每只烧杯中加入1000μL灭菌后蒸馏水将滤纸片润湿。每烧杯中分散的放入10粒萌动的杂草种子，每个处理3个重复，随机摆放于恒温光照培养箱。将烧杯盖上培养皿后置于25℃、光周期12h、光照强度6000lx的恒温培养箱中。4d后后每烧杯补充1mL蒸馏水。7d后统计各杂草的根长和茎长，按下式计算抑制率，并且计算IC50比较各化合物的除草活性。
经计算4-羟基-3-甲氧基肉桂酸乙酯对马唐的CI50为281.53mg·L-1；毒力回归方程为：y＝-14.48+5.8x；R2为：0.964。
附图说明：
图1为4-羟基-3-甲氧基肉桂酸乙酯处理马唐后的效果图 。

Claims (4)

1.一种化学药品，4-羟基-3-甲氧基肉桂酸乙酯的合成及高效除草活性。
2.权利要求1所述4-羟基-3-甲氧基肉桂酸乙酯，其特征在于：此物质合成方便，易于纯化，对马唐、反枝苋、稗草、狗尾草、虎尾草等杂草的生长均有优秀的除草活性。
3.权利要求1所述的4-羟基-3-甲氧基肉桂酸乙酯的制备方法：
反应体系：阿魏酸--30g；无水乙醇--500g；浓硫酸--1.0ml；搅拌反应，
反应温度：85℃；反应时间：5h
阿魏酸乙酯合成产品的纯化：反应体系中加入等体积的饱和NaHCO3震荡后，加入等体积的乙酸乙酯萃取。萃取后用无水Na2SO4将乙酸乙酯中的水分吸收除去，将乙酸乙酯及无水乙醇的混合物40℃下旋蒸干净既得到4-羟基-3-甲氧基肉桂酸乙酯粗品。4-羟基-3-甲氧基肉桂酸乙酯粗品过200目硅胶层析柱回收4-羟基-3-甲氧基肉桂酸乙酯组分，将洗脱剂旋蒸干净既得白色4-羟基-3-甲氧基肉桂酸乙酯纯品，其纯度可≥99％。
4.权利要求1所述的4-羟基-3-甲氧基肉桂酸乙酯的除草活性：
(1)4-羟基-3-甲氧基肉桂酸乙酯的除草谱
4-羟基-3-甲氧基肉桂酸乙酯对禾本科杂草的除草活性较高，对阔叶类杂草的除草活性相对较差。
(2)4-羟基-3-甲氧基肉桂酸乙酯的除草活性
4-羟基-3-甲氧基肉桂酸乙酯对马唐的IC50为90.13mg/L；4-羟基-3-甲氧基肉桂酸乙酯对马齿苋的IC50为155.86mg/L；4-羟基-3-甲氧基肉桂酸乙酯对播娘蒿的IC50为281.53mg/L。
CN201510645642.1A 2015-10-09 2015-10-09 4-羟基-3-甲氧基肉桂酸乙酯的高效除草活性 Pending CN106565469A (zh)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108191629A (zh) * 2018-01-18 2018-06-22 刘策 一种阿魏酸衍生物及其应用
CN109984128A (zh) * 2019-05-14 2019-07-09 上海大学 一种抑制互花米草种子萌发和幼苗生长的天然除草剂组合物及其应用
EP3503727A4 (en) * 2016-08-23 2020-08-12 Kittrich Corporation COMPOUNDS CONTAINING A MONOTERPENOID / PHENYLPROPANOID AND PROCESSES FOR THE MANUFACTURING AND USE OF THESE COMPOUNDS AS HERBICIDES
WO2023025930A1 (en) * 2021-08-27 2023-03-02 Fyteko Sa Biobased herbicide enhancer agent and method for using the same
WO2023025931A1 (en) * 2021-08-27 2023-03-02 Fyteko Sa Herbicidally active combination for agricultural applications

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999056544A1 (en) * 1998-05-01 1999-11-11 Summus Group, Ltd. Herbicidal compositions
CN101538202A (zh) * 2009-04-27 2009-09-23 东华大学 一种以氯化亚砜催化制备阿魏酸乙酯的方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999056544A1 (en) * 1998-05-01 1999-11-11 Summus Group, Ltd. Herbicidal compositions
CN101538202A (zh) * 2009-04-27 2009-09-23 东华大学 一种以氯化亚砜催化制备阿魏酸乙酯的方法

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3503727A4 (en) * 2016-08-23 2020-08-12 Kittrich Corporation COMPOUNDS CONTAINING A MONOTERPENOID / PHENYLPROPANOID AND PROCESSES FOR THE MANUFACTURING AND USE OF THESE COMPOUNDS AS HERBICIDES
CN108191629A (zh) * 2018-01-18 2018-06-22 刘策 一种阿魏酸衍生物及其应用
CN109984128A (zh) * 2019-05-14 2019-07-09 上海大学 一种抑制互花米草种子萌发和幼苗生长的天然除草剂组合物及其应用
WO2023025930A1 (en) * 2021-08-27 2023-03-02 Fyteko Sa Biobased herbicide enhancer agent and method for using the same
WO2023025931A1 (en) * 2021-08-27 2023-03-02 Fyteko Sa Herbicidally active combination for agricultural applications
BE1029718B1 (fr) * 2021-08-27 2023-03-27 Fyteko Sa Agent améliorateur d’herbicides d’origine biologique et procédé pour l’utiliser
BE1029719B1 (fr) * 2021-08-27 2023-03-27 Fyteko Sa Combinaison à activité herbicide pour des applications agricoles

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