CN114097815A - 具脒类骨架的医用化合物在抗植物病原细菌中的用途 - Google Patents
具脒类骨架的医用化合物在抗植物病原细菌中的用途 Download PDFInfo
- Publication number
- CN114097815A CN114097815A CN202111416173.8A CN202111416173A CN114097815A CN 114097815 A CN114097815 A CN 114097815A CN 202111416173 A CN202111416173 A CN 202111416173A CN 114097815 A CN114097815 A CN 114097815A
- Authority
- CN
- China
- Prior art keywords
- pathogenic bacteria
- compound
- amidine skeleton
- medical compound
- amidine
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 150000001409 amidines Chemical group 0.000 title claims abstract description 24
- 244000000005 bacterial plant pathogen Species 0.000 title claims description 8
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 claims abstract 2
- 241000207199 Citrus Species 0.000 claims description 7
- 235000020971 citrus fruits Nutrition 0.000 claims description 7
- 244000061456 Solanum tuberosum Species 0.000 claims description 5
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 244000052616 bacterial pathogen Species 0.000 abstract description 18
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract description 3
- 208000035143 Bacterial infection Diseases 0.000 abstract description 2
- 241000589655 Xanthomonas citri Species 0.000 abstract description 2
- 241000589652 Xanthomonas oryzae Species 0.000 abstract description 2
- 238000012827 research and development Methods 0.000 abstract description 2
- 241000228143 Penicillium Species 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 8
- 239000001963 growth medium Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009630 liquid culture Methods 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LTWIBTYLSRDGHP-HCURTGQUSA-N 1,2-bis[(e)-(4-chlorophenyl)methylideneamino]guanidine;hydrochloride Chemical compound [Cl-].C=1C=C(Cl)C=CC=1\C=N\N=C(/N)N\[NH+]=C\C1=CC=C(Cl)C=C1 LTWIBTYLSRDGHP-HCURTGQUSA-N 0.000 description 1
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 1
- QMNAQPMXDMLOLD-UHFFFAOYSA-N 6-methyl-4-oxo-5,6-dihydrothieno[2,3-b]thiopyran-2-sulfonamide Chemical compound S1C(C)CC(=O)C2=C1SC(S(N)(=O)=O)=C2 QMNAQPMXDMLOLD-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000531155 Pectobacterium Species 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- 229920002413 Polyhexanide Polymers 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229960002152 chlorhexidine acetate Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 229940113484 imidocarb dipropionate Drugs 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- BXBHZLHTTHMUTG-UHFFFAOYSA-N methyl 1h-pyrrolo[3,2-b]pyridine-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=N1 BXBHZLHTTHMUTG-UHFFFAOYSA-N 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 229960001753 phenformin hydrochloride Drugs 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 229960005445 robenidine hydrochloride Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
-
- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明属于药物化学领域，公开了一类具脒类骨架的医用化合物在防治由水稻白叶枯病病原菌Xanthomonas oryzae ACCC 11602、柑橘溃疡病病原菌Xanthomonas axonopodis pv.Citri和马铃薯黑胫病病原菌Pectobacterium atrosepticaACCC 19901引起的植物细菌病害中的用途。该类化合物具有易获取、成本低、杀菌谱广等特点，具有进一步研究与开发的价值。
Description
技术领域
本发明属于药物化学领域，公开了具脒类骨架的医用化合物在防治植物细菌性病害中的用途。
背景技术
目前，植物病原细菌的侵染在世界范围内发生，尤其以水稻白叶枯病病原菌、柑橘溃疡病病原菌和马铃薯黑胫病病原菌造成的病害较为严重。植物病原细菌对粮食作物造成巨大损害，导致农产品的质量和产量大幅下降。农业从业者的收入也会随之被削减。因此，急需要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原细菌的侵染。
具脒类骨架的化合物是农业和化学工业中常用的生物活性分子的关键结构单元，同时，脒作为一种重要的含氮基团，在医药方面也有非常广泛的应用。本发明所述的化合物对水稻白叶枯病病原菌、柑橘溃疡病病原菌、马铃薯黑胫病病原菌具有显著的抗菌活性，具实现“老药新用”的潜力和优势，可进一步开发其成为新型农用化学杀菌剂。
发明内容
本发明的目的是提供具脒类骨架的医用化合物在其农用抗菌方面的用途，用于防治由水稻白叶枯病病原菌、柑橘溃疡病病原菌、马铃薯黑胫病病原菌引起的植物病害。
为实现上述目的，本发明提供了如下技术方法：
本发明提供具脒类骨架的医用化合物对水稻白叶枯病病原菌Xanthomonasoryzae ACCC 11602、柑橘溃疡病病原菌Xanthomonas axonopodis pv.Citri、马铃薯黑胫病病原菌Pectobacterium atroseptica ACCC 19901抑制作用，具有以下优势：
1)本发明所涉及的具脒类骨架的医用化合物对农业病原细菌表现优异的抗菌活性，特别是对柑橘溃疡病病原菌，其中，化合物8对柑橘溃疡病病原菌MIC能达到0.78μg/mL。
2)具脒类骨架的医用化合物对植物病原细菌呈现出高活性、广谱性、原料易得等特点，具有进一步开发为新型农用抗菌剂的潜力。
具体实施方式
为了更好地理解本发明，通过以下具体实施例对本发明的上述内容做进一步的详细说明。但不应将此理解为对本发明的限制。下列实施例中所述实验方法，如无特殊说明，均为常规方法。
实施例1：化合物1～8通过商业化购置，其CAS号和纯度为：(1)盐酸氯苯胍、CAS：25875-51-8、纯度：98％；(2)聚六亚甲基双胍、CAS：27083-27-8、纯度：98％；(3)醋酸氯己定、CAS：206986-79-0、纯度：98％；(4)二丙酸咪唑苯脲、CAS：55750-06-6、纯度：95％；(5)二乙酰胺三氮脒、CAS：908-54-3、纯度：99％；(6)三氮脒、CAS：536-71-0、纯度：99％；(7)喷他脒、CAS：100-33-4、纯度：98％；(8)盐酸苯乙双胍、CAS：834-28-6、纯度：97％。
实施例2：具脒类骨架的医用化合物，其结构式如下：
实施例3：具脒类骨架的医用化合物抗植物病原细菌活性测定
本实验中所用的菌株为实验室-80℃含30％甘油冻存的菌株。将冻存菌株取出，分别在农业细菌的NB固体培养基(牛肉膏：3g，蛋白胨：5g，酵母粉：1g，蔗糖：10g，琼脂：15g，蒸馏水：1L，pH7.0；121℃灭菌20min)上面进行划线，在28℃下恒温培养直到长出单菌落。分别挑取固体培养基上单菌落至农业细菌NB液体培养基(牛肉膏：3g，蛋白胨：5g，酵母粉：1g，蔗糖：10g，蒸馏水：1L；121℃灭菌20min)在28℃、180rpm恒温摇床振荡培养到对数生长期。将在对数生长期的菌株用相应的液体培养基稀释至约106CFU/mL备用。将化合物分别用DMSO溶解，加入液体培养基中，混合均匀，配制成浓度为200μg/mL的含药液体培养基。取50μL含药培养基和相同体积的含约106CFU/mL细菌培养物加入到96孔板的孔中，最终给药浓度为100μg/mL。含等量DMSO的相同浓度100μL菌液做对照。将96孔板在28℃恒温培养箱中培养24-48h直至对照组菌液长出，在酶标仪上测定孔中菌液的OD值(OD600)。并且另外测定100μL液体培养基和浓度为100μg/mL药剂的OD值，对培养基和药剂本身造成的OD值进行矫正。校正OD值和抑制率的计算公式如下：
校正OD值＝含菌培养基OD值-无菌培养物OD值；
抑制率＝(校正后对照培养基菌液OD值-校正后含药培养基OD值)/校正后对照培养基菌液OD值×100％所有实验设置三个重复，测定得到化合物的抑制率见表1。
表1.具脒类骨架的医用化合物在100μg/mL下的抗菌活性
注：“/”表示化合物对该菌种无活性
由表1生测结果可知，本发明涉及的具脒类骨架的医用化合物对测定菌株均表现出一定的抗菌活性，其中化合物2、7、8在100μg/mL对所测试的三种菌株抑制率均为100％。
实施例4：具脒类骨架的医用化合物最低抑菌浓度(MIC)测定
将化合物的含药液体培养基在96孔板中通过二倍稀释法稀释得到系列浓度的50μL含药培养基，然后根据实施例2中相同的试验方法测定系列浓度对应的抑制率。将抑制率大于90％的最低浓度定义为MIC，测定得到的活性数据见表2。
表2.化合物的MIC值
注：“/”表示化合物的MIC值大于100μg/mL，
由表2生测结果可知，部分具脒类骨架的医用化合物对测定菌株均表现出良好的抗菌活性，其中以化合物8抑制作用最强，对柑橘溃疡病病原菌的MIC值最低可达0.78μg/mL。
综上所述，本发明所述的具脒类骨架的医用化合物对植物病原细菌均表现出一定的抑制作用，且部分化合物的抑菌活性要高于商业化阳性药噻菌铜，具有进一步研究和开发的价值。
Claims (6)
1.本发明涉及一类具脒类骨架的医用化合物在抗植物病原细菌中的新用途。
2.根据权利要求1所述的用途，其中，具脒类骨架的医用化合物，具有如下的分子结构特征：
3.根据权利要求1所述的用途，具脒类骨架的医用化合物在防治植物病原细菌引起的病害中的用途。
4.根据权利要求1至3所述的用途，具脒类骨架的医用化合物在防治水稻白叶枯病中的用途。
5.根据权利要求1至3所述的用途，其中，具脒类骨架的医用化合物在防治柑橘溃疡病中的用途。
6.根据权利要求1至3所述的用途，其中，具脒类骨架的医用化合物在防治马铃薯黑胫病中的用途。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111416173.8A CN114097815A (zh) | 2021-11-25 | 2021-11-25 | 具脒类骨架的医用化合物在抗植物病原细菌中的用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111416173.8A CN114097815A (zh) | 2021-11-25 | 2021-11-25 | 具脒类骨架的医用化合物在抗植物病原细菌中的用途 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114097815A true CN114097815A (zh) | 2022-03-01 |
Family
ID=80373517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111416173.8A Pending CN114097815A (zh) | 2021-11-25 | 2021-11-25 | 具脒类骨架的医用化合物在抗植物病原细菌中的用途 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114097815A (zh) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1096921A (zh) * | 1992-10-20 | 1995-01-04 | 株式会社油公 | 杀菌组合物及含有该组合物的皂 |
| CN1312681A (zh) * | 1998-06-12 | 2001-09-12 | 明治制果株式会社 | 农业或园艺用细菌性病害防除剂 |
| CN103210948A (zh) * | 2013-05-07 | 2013-07-24 | 江苏辉丰农化股份有限公司 | 一种防治果树病害的杀菌剂 |
| CN103229778A (zh) * | 2013-05-07 | 2013-08-07 | 江苏辉丰农化股份有限公司 | 一种防治禾谷类作物病害的杀菌剂 |
| CN104186524A (zh) * | 2014-09-02 | 2014-12-10 | 海南正业中农高科股份有限公司 | 含聚六亚甲基双胍或其盐的杀菌组合物 |
-
2021
- 2021-11-25 CN CN202111416173.8A patent/CN114097815A/zh active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1096921A (zh) * | 1992-10-20 | 1995-01-04 | 株式会社油公 | 杀菌组合物及含有该组合物的皂 |
| CN1312681A (zh) * | 1998-06-12 | 2001-09-12 | 明治制果株式会社 | 农业或园艺用细菌性病害防除剂 |
| CN103210948A (zh) * | 2013-05-07 | 2013-07-24 | 江苏辉丰农化股份有限公司 | 一种防治果树病害的杀菌剂 |
| CN103229778A (zh) * | 2013-05-07 | 2013-08-07 | 江苏辉丰农化股份有限公司 | 一种防治禾谷类作物病害的杀菌剂 |
| CN104186524A (zh) * | 2014-09-02 | 2014-12-10 | 海南正业中农高科股份有限公司 | 含聚六亚甲基双胍或其盐的杀菌组合物 |
Non-Patent Citations (1)
| Title |
|---|
| K.A.NGUYEN等: "Quaternary Ammonium Compounds as New Sanitizers for Reducing the Spreadof the Olive Knot Pathogen on Orchard Equipment", PLANT DISEASE, vol. 101, no. 7, pages 1188 - 1193 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113367133B (zh) | 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 | |
| CN113455507B (zh) | 天然源黄酮类化合物作为抗菌剂在抑制植物病原细菌中的应用 | |
| CN114145299B (zh) | 一类具水杨酸结构骨架的衍生物在抗植物病原细菌和人源病菌中的应用 | |
| CN113545349B (zh) | 一种1,3-二羰基-4-三氟甲基类化合物在抗植物病原细菌中的应用 | |
| CN104705324B (zh) | 一种含中生菌素和壳寡糖的杀菌组合物 | |
| CN108450462A (zh) | 法尼醇对甲氧基丙烯酸类杀菌剂在防治黑粉病中的增效应用 | |
| CN114097815A (zh) | 具脒类骨架的医用化合物在抗植物病原细菌中的用途 | |
| CN114304161A (zh) | 三氯苯达唑在防治农业病原菌中的用途 | |
| CN107333783A (zh) | 含茉莉酸甲酯的组合物在柑橘溃疡病的应用 | |
| CN114009441A (zh) | 具哌嗪和哌啶骨架的医用化合物在抗植物病原细菌中的用途 | |
| CN114009443B (zh) | 截短侧耳素类化合物在抗植物病原细菌中的用途 | |
| CN112772658A (zh) | 一种粉红螺旋聚孢霉孢子与啶酰菌胺的杀菌组合物及应用 | |
| CN114009439B (zh) | 一类含氮离子化合物在抗植物病原细菌和人源病菌中的用途 | |
| CN113994971A (zh) | 激酶抑制剂在防治农业病原细菌中的用途 | |
| CN117402202B (zh) | 一种化合物及其制备方法和用途以及含该化合物的药物组合物和医疗器械涂层 | |
| CN114041461A (zh) | 双氯酚在防治农业病原菌中的用途 | |
| CN115005223B (zh) | 吲哚3,4位并九元中环化合物的新用途 | |
| CN114009440A (zh) | 阿巴芬净在防治农业病原菌中的用途 | |
| CN114190394B (zh) | 一种用于澳洲坚果育种的抗果实黑斑病激活剂 | |
| CN114304154A (zh) | 羰基氰化氯苯腙在防治农业病原菌中的用途 | |
| CN116114712B (zh) | 一种包含解淀粉芽孢杆菌杀菌组合物及其应用 | |
| 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 | |
| CN112825858B (zh) | 2,5呋喃二甲醛肟在抗菌除霉消毒剂中的应用 | |
| CN109479878B (zh) | 2-甲氧基苯丙酸化合物在预防和/或治疗植物病害中的应用 | |
| 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 |
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 |