CN112219851B - 3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 - Google Patents
3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 Download PDFInfo
- Publication number
- CN112219851B CN112219851B CN202011110599.6A CN202011110599A CN112219851B CN 112219851 B CN112219851 B CN 112219851B CN 202011110599 A CN202011110599 A CN 202011110599A CN 112219851 B CN112219851 B CN 112219851B
- Authority
- CN
- China
- Prior art keywords
- iso
- quinoline
- active ingredient
- substituted flavonoid
- flavonoid derivative
- 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.)
- Expired - Fee Related
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 16
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract description 10
- 239000004480 active ingredient Substances 0.000 title claims abstract description 8
- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 7
- 150000002214 flavonoid derivatives Chemical class 0.000 title abstract description 17
- 241000221696 Sclerotinia sclerotiorum Species 0.000 claims abstract description 14
- 241000123650 Botrytis cinerea Species 0.000 claims abstract description 11
- 229930003935 flavonoid Natural products 0.000 claims description 9
- -1 flavonoid compound Chemical class 0.000 claims description 9
- 235000017173 flavonoids Nutrition 0.000 claims description 9
- 241000222199 Colletotrichum Species 0.000 claims description 5
- 240000008067 Cucumis sativus Species 0.000 claims description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 244000241235 Citrullus lanatus Species 0.000 claims description 3
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 claims description 3
- 244000061176 Nicotiana tabacum Species 0.000 claims description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 10
- 244000052769 pathogen Species 0.000 abstract description 6
- 230000001717 pathogenic effect Effects 0.000 abstract description 6
- 239000003899 bactericide agent Substances 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 6
- 235000009754 Vitis X bourquina Nutrition 0.000 description 5
- 235000012333 Vitis X labruscana Nutrition 0.000 description 5
- 240000006365 Vitis vinifera Species 0.000 description 5
- 235000014787 Vitis vinifera Nutrition 0.000 description 5
- 239000005747 Chlorothalonil Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002215 flavonoids Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 3
- 244000000004 fungal plant pathogen Species 0.000 description 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 3
- 235000005875 quercetin Nutrition 0.000 description 3
- 229960001285 quercetin Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 241000511821 Altenia Species 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 241001512566 Valsa mali Species 0.000 description 2
- 229940124350 antibacterial drug Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ZWSNUPOSLDAWJS-QNDFHXLGSA-N 6,7-dihydroxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one Chemical compound OC[C@H]1O[C@@H](Oc2ccc(cc2)-c2coc3cc(O)c(O)cc3c2=O)[C@H](O)[C@@H](O)[C@@H]1O ZWSNUPOSLDAWJS-QNDFHXLGSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000745988 Phyllostachys Species 0.000 description 1
- 241001115351 Physalospora Species 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002207 flavanone derivatives Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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
- 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
- A01N43/42—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 condensed with carbocyclic rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明公开了一种3‑位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用。结果表明，本发明的喹啉或异喹啉基取代黄酮类衍生物具有广谱性抗真菌活性，尤其对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌抑制活性显著，为开发以3‑位(异)喹啉取代黄酮类衍生物为活性成分的新型杀菌剂提供了基础。
Description
技术领域
本发明属于药物化学技术领域，具体涉及一种3-位(异)喹啉取代黄酮类衍生物的抗真菌应用。
背景技术
黄酮类化合物又称为类黄酮，是自然界中尤其是植物中广泛存在的一类天然产物。根据A、B和C环上取代基的不同与化学性质的差别可将黄酮类化合物分为14个大类，包括黄酮、异黄酮、查尔酮、黄酮醇、二氢黄酮和色原酮等。从1931年Walz从豆科植物中成功分离出大豆异黄酮糖苷以来，黄酮类化合物的研究一直是国内外科学家们关注的热点。研究发现黄酮类化合物具有一定的抗菌作用，该类化合物的抑菌机制主要有：抑制细菌的能量代谢，干扰细菌的细胞壁，破坏细胞膜的完整性，增加细胞膜的通透性等，抑制或破坏病原菌的生长，导致其死亡，从而达到防治病害的目的。
近年来由于长期使用传统杀菌剂，使得杀菌剂抗性问题日益凸显，因此迫切需要开发新的抗菌药物，而黄酮类化合物作为一种植物源化合物，目前还不存在耐药性问题，具有成为新型杀菌药物的潜力。而已有的黄酮类化合物由于存在抗菌活性较差等问题，而无法实现进一步应用。因此迫切需要开发一种具有高效杀菌活性且毒副作用小的新型黄酮类衍生物。
发明内容
本发明的目的为3-位(异)喹啉取代黄酮类衍生物提供一种新的应用。
本发明3-(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用，通过将一系列3-位(异)喹啉黄酮类衍生物应用到不同真菌病害中，鉴定结果显示对油菜菌核病、苹果腐烂病病和葡萄灰霉病的抑制效果尤为显著。
本发明所述3-位(异)喹啉取代黄酮类衍生物的结构式如式I或式II所示：
其中，R1代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素、苯基中任意一种，R2和R4各自独立的代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素中的任意一种且其中至少有一个为H，R3代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素、苯基中任意一种取代的苯基或者代表C1～C4烷基或环丙基。
本发明的有益效果如下：
本发明的3-位(异)喹啉取代黄酮类衍生物具有广谱性抗真菌活性，尤其对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌抑制活性显著，为开发以3-位(异)喹啉取代黄酮类衍生物为活性成分的新型杀菌剂奠定了基础。
具体实施方式
下面结合实施例对本发明进一步详细的说明，但本发明的保护范围不仅限于这些实施例。
实施例1
根据公布号为CN110790752A、发明名称为“一种(异)喹啉和喹喔啉取代的黄酮及喹诺酮衍生物的合成方法”中公开的方法合成下述式1～20所示的3-喹啉取代黄酮类衍生物，以及式21～33所示的3-异喹啉取代黄酮类衍生物。
1、实验方法
采用菌丝线性生长速率法，分别测定式1～33化合物对黄瓜炭疽病菌、西瓜枯萎病菌、油菜菌核病菌、苹果纶纹病菌、苹果腐烂病菌、烟草赤星病菌和葡萄灰霉病菌7种供试植物病原真菌的体外抑制活性。所选真菌由西北农林科技大学植物保护学校提供。
分别以50mg/L的槲皮素和百菌清溶液为阳性对照，以5％的DMSO水溶液作为空白对照，将已准确称量的待测化合物完全溶于5％的DMSO(v/v)水溶液中，将10mL待测液或对照液与90mL无菌PDA培养基在50℃快速混匀，得到质量浓度为50mg/L的含药液；将其趁热倒入已灭菌的培养皿内，每皿10mL，冷却备用。将供试植物病原真菌(菌饼直径5mm)接种到上述培养皿中，每个测试组设3个平行；将其置于25℃的恒温培养箱中培养72h后，采用十字交叉法测量菌落直径(mm)，按式(1)计算菌丝生长抑制率(IR)：
IR(％)＝[(dc-d0)-(ds-d0)]/(dc-d0)×100 (1)
式中：d0为菌饼直径(5mm)，dc为空白对照组菌落平均直径(mm)，ds为样品组菌落平均直径(mm)。
2、实验结果
表1不同3-(异)喹啉取代类衍生物的体外抑菌活性(抑制率，％)
注：表中数据为3次重复实验的平均值；C.o:Colletotrichum orbiculare(黄瓜炭疽病菌)；F.o:Fusarium oxysporum(西瓜枯萎病菌)；S.c:Sclerotinia sclerotiorum(油菜菌核病菌)；P.p:Physalospora piricola(苹果纶纹病菌)；V.m:Valsa mali(苹果腐烂病)；A.a:Altenaria alternariae(烟草赤星病菌)；B.p:Botrytis cinerea(葡萄灰霉病菌)；Quercetin(槲皮素)；Ci:Chlorothalonil(百菌清)。
从表1中分析可得出，式1～33化合物对所选供试植物病原真菌黄瓜炭疽病菌、西瓜枯萎病菌、油菜菌核病菌、苹果纶纹病菌、苹果腐烂病菌、烟草赤星病菌、对葡萄灰霉病中至少一种甚至多种表现出良好的抑制作用，并且对葡萄灰霉病的抑制率超过80％，其中式1化合物对葡萄灰霉病抑制率更高达90％。此外，式3化合物对油菜菌核病菌和苹果腐烂病菌的抑制率达到93％，式4化合物对苹果腐烂病的抑制率也超过92％；而式6化合物对油菜菌核病菌和苹果腐烂病菌的抑制率均达100％，对葡萄灰霉病的抑制率也超过95％；式11化合物对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌的抑制率菌超过96％；式13化合物对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌的抑制率菌超过93％；而式20、22和23化合物对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌的抑制率菌超过95％；而式24化合物对油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌的抑制率菌高达100％，远优于商品化抗菌剂百菌清。这表明本发明的3-(异)喹啉取代黄酮类衍生物均具有抗真菌活性，尤其对于油菜菌核病菌、苹果腐烂病菌和葡萄灰霉病菌表现出优异的抑菌活性，为进一步研究不同化合物的抑菌活性提供了方向，并且为制备以3-(异)喹啉取代黄酮类衍生物为主要抗真菌活性成分的杀菌剂奠定了基础。
Claims (1)
1.3-（异）喹啉取代黄酮类化合物作为抗真菌活性成分的应用，所述的3-位（异）喹啉取代黄酮类化合物的结构式如式I或式II所示：
其中，R1代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素、苯基中任意一种，R2和R4各自独立的代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素中的任意一种且其中至少有一个为H，R3代表H、C1～C4烷基、C1～C4烷氧基、CF3、卤素、苯基中任意一种取代的苯基或者代表C1～C4烷基或环丙基；
所述的真菌为黄瓜炭疽病菌、西瓜枯萎病菌、油菜菌核病菌、苹果纶纹病菌、苹果腐烂病菌、烟草赤星病菌、葡萄灰霉病菌中任意一种。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011110599.6A CN112219851B (zh) | 2020-10-16 | 2020-10-16 | 3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011110599.6A CN112219851B (zh) | 2020-10-16 | 2020-10-16 | 3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112219851A CN112219851A (zh) | 2021-01-15 |
| CN112219851B true CN112219851B (zh) | 2021-09-21 |
Family
ID=74117794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011110599.6A Expired - Fee Related CN112219851B (zh) | 2020-10-16 | 2020-10-16 | 3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112219851B (zh) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256411B (zh) * | 2019-06-03 | 2022-06-07 | 华侨大学 | 一种2，3-二取代苯并-γ-吡喃酮衍生物的制备方法 |
| CN110790752B (zh) * | 2019-11-12 | 2022-08-23 | 陕西师范大学 | 一种（异）喹啉和喹喔啉取代的黄酮及喹诺酮衍生物的合成方法 |
-
2020
- 2020-10-16 CN CN202011110599.6A patent/CN112219851B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN112219851A (zh) | 2021-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102771502A (zh) | 一种含氰烯菌酯和酰胺类杀菌剂的杀菌组合物 | |
| Hemalatha et al. | Antimicrobial effect of separate extract of acetone, ethyl acetate, methanol and aqueous from leaf of Milkweed (Calotropis gigantea L.) | |
| CN109232545A (zh) | 一种含喹喔啉的杨梅素衍生物、其制备方法及用途 | |
| CN105248424A (zh) | 杀菌组合物及其应用 | |
| CN110563645A (zh) | 一种新型喹诺酮类化合物及其制备方法和应用 | |
| CN103694155A (zh) | 新型取代苯丙(烯)醛缩氨基硫脲类化合物及其作为农用杀菌剂的应用 | |
| CN104450580A (zh) | 放线菌素d的制备方法及其应用 | |
| CN104059027A (zh) | 一类含1, 2, 4-三唑的(e)-甲氧基亚氨基苯乙酸甲酯类化合物及其制备方法和用途 | |
| Asghar et al. | A review on anti-urease potential of coumarins | |
| CN112219851B (zh) | 3-位(异)喹啉取代黄酮类衍生物作为抗真菌活性成分的应用 | |
| CN113598188A (zh) | 4’-去甲基表鬼臼毒素作为农用杀菌剂的用途 | |
| Odekina et al. | Antimicrobial and antioxidant activities of novel marine bacteria (Bacillus 2011SOCCUF3) isolated from marine sponge (Spongia officinalis) | |
| CN103524418B (zh) | 一组3-甲基吡唑化合物 | |
| CN103535358B (zh) | 一组邻位取代苯甲酰化合物的杀菌剂用途 | |
| CN113632800B (zh) | 生物碱在防治茶树叶部病害中的应用 | |
| CN114805154A (zh) | 大蒜素类衍生物及其制备方法和应用 | |
| Belakhov et al. | Imbricin, an antifungal antibiotic of non-medical application: Preparation, physicochemical properties, structural features, and industrial and agricultural uses | |
| CN103141486B (zh) | 4-(苯并呋喃-5-基)-2-苯氨基噻唑作为杀菌剂的应用 | |
| CN103524407B (zh) | 一组2-氟-3-吡啶甲酰化合物 | |
| CN108794461B (zh) | 一种含氟苯基噁二唑连吡唑类杀虫杀菌剂 | |
| Olawuyi et al. | Studies on antibacterial activities of Fomes lignosus-A Nigerian mushroom | |
| CN114621214B (zh) | 一种抗菌席夫碱n-酰化物及其制备方法和应用 | |
| CN113004240B (zh) | 苯并吡喃类化合物及其在农药中的用途 | |
| Sridevi et al. | Antibacterial activity of some higher plant floral petals | |
| CN104488902B (zh) | 含甲磺酰菌唑与嘧啶类或喹啉类杀菌剂的复配组合物 |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210921 |