CN115413659A - 一种肉桂酸衍生物在防治农业病原真菌中的应用 - Google Patents

一种肉桂酸衍生物在防治农业病原真菌中的应用 Download PDF

Info

Publication number
CN115413659A
CN115413659A CN202211107939.9A CN202211107939A CN115413659A CN 115413659 A CN115413659 A CN 115413659A CN 202211107939 A CN202211107939 A CN 202211107939A CN 115413659 A CN115413659 A CN 115413659A
Authority
CN
China
Prior art keywords
cinnamic acid
pathogenic fungi
agricultural
acid derivative
application
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202211107939.9A
Other languages
English (en)
Inventor
李安平
师彦平
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gansu Institute For Drug Control
Lanzhou Institute of Chemical Physics LICP of CAS
Original Assignee
Gansu Institute For Drug Control
Lanzhou Institute of Chemical Physics LICP of CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gansu Institute For Drug Control, Lanzhou Institute of Chemical Physics LICP of CAS filed Critical Gansu Institute For Drug Control
Priority to CN202211107939.9A priority Critical patent/CN115413659A/zh
Publication of CN115413659A publication Critical patent/CN115413659A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

本发明公开了一系列肉桂酸衍生物在防治农业病原真菌中的应用，属于天然药物化学领域农药科学领域。抑菌活性测定结果显示，本发明的肉桂酸衍生物对油菜菌核病菌、立枯丝核病菌、小麦赤霉病菌、番茄灰霉病菌、辣椒疫霉病菌、稻瘟病菌等6种农业病原真菌具有显著的抗菌活性，可进一步开发其成为新型农用杀菌剂。

Description

一种肉桂酸衍生物在防治农业病原真菌中的应用
技术领域
本发明涉及一种肉桂酸衍生物在防治农业病原真菌中的应用，属于天然药物化学领域和农药科学领域。
背景技术
植物病菌感染是导致农产品质量和产量大幅下降的原因之一，由于新传染病的频发和现有药物产生耐药性的病原微生物数量增加，植物病菌引起的植物病害给农业造成巨大的产量和经济损失，威胁全球粮食安全和公众健康，进而导致农业从业者的收入随之削减。因此，急需积极探索出具有广泛杀菌谱和全新作用靶标的杀菌剂以抵抗植物病菌的侵染。
天然产物独特的分子结构为药物化学家提供了药物设计的宝贵灵感。目前，从天然产物中发现新的先导化合物以提高疗效和对抗耐药性仍被认为是最有效的策略之一。肉桂酸是从肉桂皮或安息香分离出的有机酸，是植物组织中由苯丙氨酸脱氨降解产生的苯丙烯酸，广泛分布于蜂胶、蔬菜和水果等天然物质中，由于其结构简单、原料易得、毒性低且具有广泛的生物活性，已成为抗菌领域重要的研究方向之一。
发明内容
本发明的目的是通过肉桂酸衍生物对农业病原真菌的抑制作用，尤其是对油菜菌核病菌、立枯丝核病菌、小麦赤霉病菌、番茄灰霉病菌、辣椒疫霉病菌、稻瘟病菌的抑制作用进行研究，以用于防治由其引起的植物病害。
为了研究肉桂酸衍生物对植物病原真菌的抑制作用，分别测定了73种不同化学结构的肉桂酸衍生物对油菜菌核病菌、立枯丝核病菌、小麦赤霉病菌、番茄灰霉病菌、辣椒疫霉病菌、稻瘟病菌的抑制率。
供试菌种油菜菌核病菌、立枯丝核病菌、小麦赤霉病菌、番茄灰霉病菌、辣椒疫霉病菌、稻瘟病菌，由甘肃省农业科学院提供。
所述73种肉桂酸衍生物的分子结构式如下：
Figure 545498DEST_PATH_IMAGE001
Figure DEST_PATH_IMAGE002
Figure 728218DEST_PATH_IMAGE003
Figure DEST_PATH_IMAGE004
Figure 39113DEST_PATH_IMAGE005
Figure DEST_PATH_IMAGE006
。
抗菌活性测试方法：采用马铃薯葡萄糖琼脂培养基（PDA培养基）进行。其制备方法如下：先将马铃薯洗净去皮，称取200g切成小块，加水煮烂（煮沸20-30分钟，马铃薯块能被玻璃棒戳破即可），用八层纱布过滤，加热，再加15g琼脂，继续加热搅拌混匀，待琼脂溶解完后，加入葡萄糖，搅拌均匀，稍冷却后再补足水分至1000毫升，分装锥形瓶，加塞、包扎，115℃灭菌2h，备用。将化合物H-01~H-22分别用DMSO溶解，加入培养基中，混合均匀，使培养基中的化合物浓度分别为50μg/mL、250μg/mL，以等浓度的DMSO作为空白对照，以上市药物嘧菌酯为阳性对照。倒平板，冷却后分别接菌，置于23摄氏度培养箱中培养，以空白对照菌丝长满培养皿为限，测定各化合物的抑菌率。所有试验设三个平行组或重复三次。抑菌率的计算按下述计算公式进行：
抑菌率 =
Figure 8557DEST_PATH_IMAGE007
100%
测试结果见表1、2。结果表明本发明涉及的肉桂酸衍生物对部分病原菌抑菌效果表现优异，通过降浓度，利用SPSS软件求出半数效应浓度（EC50），测定得到的活性数据见表3。
Figure DEST_PATH_IMAGE008
Figure 88508DEST_PATH_IMAGE009
Figure DEST_PATH_IMAGE010
Figure 442129DEST_PATH_IMAGE011
由表1-3的测定结果可知，本发明涉及的肉桂酸衍生物对所测试病原菌具有一定的抗菌活性，特别是化合物A-1至A-5，A-7至A-18对立枯丝核菌表现出较高的活性，其EC50 值为1.0-4.96 μg/mL，且化合物A-11对立枯丝核菌的活性最好，EC50 值为1.0 μg/mL。可作为新的杀菌剂进一步设计与开发。

Claims (1)

1.一种肉桂酸衍生物在防治农业病原真菌中的应用，其特征在于：所述农业病原真菌为油菜菌核病菌、立枯丝核病菌、小麦赤霉病菌、番茄灰霉病菌、辣椒疫霉病菌、稻瘟病菌；所述肉桂酸衍生物的分子结构式如下：
Figure DEST_PATH_IMAGE001
Figure 372402DEST_PATH_IMAGE002
Figure DEST_PATH_IMAGE003
Figure 86280DEST_PATH_IMAGE004
Figure DEST_PATH_IMAGE005
Figure 646444DEST_PATH_IMAGE006
。
CN202211107939.9A 2022-09-13 2022-09-13 一种肉桂酸衍生物在防治农业病原真菌中的应用 Pending CN115413659A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211107939.9A CN115413659A (zh) 2022-09-13 2022-09-13 一种肉桂酸衍生物在防治农业病原真菌中的应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211107939.9A CN115413659A (zh) 2022-09-13 2022-09-13 一种肉桂酸衍生物在防治农业病原真菌中的应用

Publications (1)

Publication Number Publication Date
CN115413659A true CN115413659A (zh) 2022-12-02

Family

ID=84202323

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211107939.9A Pending CN115413659A (zh) 2022-09-13 2022-09-13 一种肉桂酸衍生物在防治农业病原真菌中的应用

Country Status (1)

Country Link
CN (1) CN115413659A (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111387185A (zh) * 2020-05-08 2020-07-10 兰州大学 一种萘替芬类似物在防治农业植物病害中的用途
CN113367133A (zh) * 2021-07-08 2021-09-10 中国科学院兰州化学物理研究所 肉桂酸及其衍生物作为抗菌剂在抑制植物病原细菌中的应用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111387185A (zh) * 2020-05-08 2020-07-10 兰州大学 一种萘替芬类似物在防治农业植物病害中的用途
CN113367133A (zh) * 2021-07-08 2021-09-10 中国科学院兰州化学物理研究所 肉桂酸及其衍生物作为抗菌剂在抑制植物病原细菌中的应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
张矛: "喹喔啉苯腙衍生物和肉桂酰胺衍生物的合成及生物活性研究" *

Similar Documents

Publication Publication Date Title
Khairy et al. Eco-friendly application of nano-chitosan for controlling potato and tomato bacterial wilt
KR100365151B1 (ko) 어류 병원성 세균과 바이러스의 감염 예방 및 치료를 위한δ-아미노레불린산의 신규한 용도
JP2022529137A (ja) 官能基化された二酸化チタンのナノ粒子化合物の様々な使用方法
CN112715541A (zh) 啤酒花中黄腐醇和异黄腐酚在防治农业病害中的用途
CN115039775B (zh) 二羧酸类化合物对附着胞形成的抑制作用及其用途
CN115413659A (zh) 一种肉桂酸衍生物在防治农业病原真菌中的应用
CN117084246A (zh) 一种含白藜芦醇的杀菌组合物
CN114304161B (zh) 三氯苯达唑在防治农业病原菌中的用途
CN110463715A (zh) 五味子甲素及类似物在农业病害防治中的应用
CN107136073A (zh) 一种含有大黄素甲醚与甲氧基丙烯酸酯类杀菌剂组合物
CN115413658A (zh) 一种肉桂酸衍生物在防治农业病原霉菌中的应用
CN113575583B (zh) 一种预防或治疗植物炭疽病的产品和应用
CN104904714B (zh) 丁酸钠在制备用于防治由植物病原菌引起的植物病害的杀菌剂中的用途
CN114027310B (zh) 一种硫代氨基甲酸类化合物在防治农业病原真菌中的用途
CN114097807B (zh) 巴多索隆类化合物在抗农业病原真菌中的用途
Paul et al. Synergistic-antagonistic antibacterial potential of chitosan composites with Moringa oleifera leaf powder
CN110122496B (zh) 一种含二氯异氰尿酸钠和喹啉铜的药物组合物及其应用
CN114190394B (zh) 一种用于澳洲坚果育种的抗果实黑斑病激活剂
CN114052029A (zh) 具哌嗪和哌啶骨架的医用化合物在防治植物真菌病害中的用途
CN114041461A (zh) 双氯酚在防治农业病原菌中的用途
CN100515197C (zh) 天然除虫菊素乳油制剂的应用
Kam et al. Development of clove (Syzygium aromaticum) and cinnamon (Cinnamomum burmannii) based food sanitizer.
CN116746578A (zh) 一种二芳醚-氟化1,3-二羰基化合物在抗微生物感染中的用途
CN117084245A (zh) 一种含白藜芦醇的农药组合物
CN104920360A (zh) 丁苯羟酸在制备用于防治由植物病原菌引起的植物病害的杀菌剂中的用途

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20221202