CN108675991A - 一种含氟吡啶哌嗪咪唑脲及其应用 - Google Patents
一种含氟吡啶哌嗪咪唑脲及其应用 Download PDFInfo
- Publication number
- CN108675991A CN108675991A CN201810668834.8A CN201810668834A CN108675991A CN 108675991 A CN108675991 A CN 108675991A CN 201810668834 A CN201810668834 A CN 201810668834A CN 108675991 A CN108675991 A CN 108675991A
- Authority
- CN
- China
- Prior art keywords
- fluorine
- formula
- compound
- containing pyridine
- piperazine imidazoles
- 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.)
- Granted
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 9
- 239000011737 fluorine Substances 0.000 title claims abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 9
- PJCKOBASFUXPNB-UHFFFAOYSA-N N1C=NC=C1.N1CCNCC1.N1=CC=CC=C1 Chemical class N1C=NC=C1.N1CCNCC1.N1=CC=CC=C1 PJCKOBASFUXPNB-UHFFFAOYSA-N 0.000 title description 5
- 239000004202 carbamide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 9
- -1 pyridine piperazine imidazoles carbamide compounds Chemical class 0.000 claims abstract description 4
- 239000000645 desinfectant Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 2
- 230000000975 bioactive effect Effects 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 8
- 241000233616 Phytophthora capsici Species 0.000 abstract description 6
- 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 abstract description 3
- 241000213004 Alternaria solani Species 0.000 abstract description 3
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 3
- 244000105624 Arachis hypogaea Species 0.000 abstract description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 3
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 3
- 241000555706 Botryosphaeria dothidea Species 0.000 abstract description 3
- 241001157813 Cercospora Species 0.000 abstract description 3
- 241000395107 Cladosporium cucumerinum Species 0.000 abstract description 3
- 240000008067 Cucumis sativus Species 0.000 abstract description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 3
- 241000189458 Dothidea Species 0.000 abstract description 3
- 241000223218 Fusarium Species 0.000 abstract description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 3
- 208000031888 Mycoses Diseases 0.000 abstract description 3
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 3
- 235000020232 peanut Nutrition 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical class FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 1
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000002068 microbial inoculum Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910000027 potassium carbonate Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical group O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Pyridine Compounds (AREA)
Abstract
本发明公开了一种含氟吡啶哌嗪咪唑脲类化合物，结构如式I所示：
Description
技术领域 本发明属于农用杀菌剂领域，具体涉及一种含氟吡啶哌嗪咪唑脲及其作为农用杀菌剂的用途。
背景技术 在农作物和蔬菜侵染性病害中，主要有真菌性病害和细菌性病害两种，其中真菌性病害种类多且普遍，约占病害的80％，会造成农作物和蔬菜的大幅度减产，因此开发高效杀菌剂一直是农药领域的重点之一。含氟吡啶类化合物是一种重要的吡啶衍生物，在农药、医药等领域都有应用；含有哌嗪杂环的化合物在农药中也有应用，如内吸性杀菌剂嗪胺灵结构中含有哌嗪杂环；咪唑类化合物常有杀菌活性。在现有技术中，如本发明式I所示的含氟吡啶哌嗪咪唑脲及其杀菌活性，未见公开。
发明内容 本发明的目的在于提供一种结构新颖、高效、安全的农用杀菌剂。
本发明的技术方案如下：
一种含氟吡啶哌嗪咪唑脲，结构如式I所示：
式I化合物可由如下反应制得：
式Ⅲ化合物与式Ⅱ化合物在缚酸剂存在下反应生成式Ⅰ化合物，缚酸剂选自三乙胺、吡啶或取代吡啶、碳酸钠或碳酸钾；反应所用溶剂选自乙腈、乙酸乙酯、二氯甲烷等。中间体式Ⅲ化合物和式Ⅰ化合物的具体制备方法见本发明合成实例。
本发明的优点和积极效果：
本发明是以哌嗪为桥链，将三氟甲基吡啶和咪唑连接生成一种脲类化合物，是一种结构新颖的杀菌剂，由于在化合物中同时存在三氟甲基吡啶基、哌嗪、咪唑结构，显著提高了其内吸传导作用，使其具有意想不到的高杀菌活性，且杀菌谱广(见表1)；同时，原料易得，合成工艺简单，生产成本低，毒性低、用药量小，符合现代农业对低公害、超高效、长持效的要求，具有商品化潜力。
本发明还包括式I化合物作为活性组分的杀菌组合物，该组合物还包括农业或林业上可接受的载体。
本发明化合物在防治作物菌害时，可单独使用，也可与其它活性物质组合使用，以利于提高产品的综合功能。
本发明的组合物以制剂的形式使用：式I化合物作为活性组分溶于或分散于载体或试剂中，添加适当的表面活性剂配制成乳油、水乳剂、微乳剂、悬浮剂等。
应明确的是，在本发明的权利要求所限定的范围内，可进行各种变换和改动。
具体实施方式：
下列合成实例及生测试验结果可用来进一步说明本发明，但不意味着限制本发明。
合成实例
实例1、式Ⅰ化合物的制备
(1)中间体Ⅲ的制备：
称取17.2g(0.2mol)无水哌嗪加入250mL反应瓶中，加入60mL甲醇，搅拌溶解并升温至40℃，然后用50mL甲醇溶解21.6g(0.1mol)2,3-二氯-5-(三氟甲基)吡啶，缓慢滴加入反应瓶中，滴毕，于40℃恒温反应6h，TLC跟踪至原料反应完全，降至室温，抽滤，将滤液旋蒸除去甲醇，析出白色固体，加水搅拌溶解剩余的无水哌嗪，抽滤、水洗滤饼2次，得白色固体23.2g，熔点65.3～67.1℃，收率为87.5％。
1H NMR(500MHz,DMSO-d6),δ(ppm)8.53(s,1H),8.15(s,1H),3.37–3.35(t,4H),2.82–2.80(t,4H)。
(2)化合物I的制备：
取3.98g(0.015mol)中间体Ⅲ加入250mL反应瓶中，加入30mL乙腈做溶剂，再加入1.67g三乙胺做缚酸剂，滴加式Ⅱ化合物2.43g(0.015mol)，滴毕，在60℃下反应至反应完全(TLC板跟踪反应)。加入50mL水搅拌，有白色固体析出，减压抽滤，所得固体烘干，得5.04g，收率为93％。熔点110.1～111.8℃。
1H NMR(500MHz,DMSO-d6)δ(ppm)8.57(s,1H),8.23(s,1H),8.06(s,1H),7.51(s,1H),7.03(s,1H),3.71-3.62(m,4H),3.56-3.573(dd,J＝6.4,3.5Hz,4H)
生物活性测定
实例2、杀菌活性试验
将一定量药剂溶解在适量DMF内，然后用乳化水稀释至50mg/L。采用离体平皿法，供试病原菌：番茄早疫病菌(A.solani)、黄瓜枯萎病菌(C.cucumerinum)、花生褐斑病菌(C.rachidicola)、苹果轮纹病菌(Botryospharia dothidea)、辣椒疫霉菌(Phytophthoracapsici Leonian)。
采用菌体生长速率测定法(mycelium growth rate test)，具体过程是：在无菌条件下各吸取1mL药液注入培养皿内，加入9mLPDA培养基，摇匀后制成50mg/L含药平板，以添加1mL灭菌水的平板做空白对照。用直径4mm的打孔器沿菌丝外缘切取菌盘，移至含药平板上，每次处理重复三次。将培养皿放在24±1℃恒温培养箱内培养，72h后调查各处菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率。
防效(％)＝(空白菌落直径－处理菌落直径)/(空白菌落直径－4)×100％
测定了目标化合物对番茄早疫病菌(A.solani)、黄瓜枯萎病菌(C.cucumerinum)、花生褐斑病菌(C.rachidicola)、苹果轮纹病菌(Botryospharia dothidea)、辣椒疫霉菌(Phytophthora capsici Leonian)五种菌体的杀菌活性,测试浓度为100μg/mL和10μg/mL，抑菌率效果列于表1中。
表1式I化合物在100μg/mL和10μg/mL下对5种病菌的抑菌率
从生物活性数据可以看出式I化合物有优异的杀菌效果。
Claims (3)
1.一种含氟吡啶哌嗪咪唑脲类化合物，结构如式I所示：
2.根据权利要求1所述的一种含氟吡啶哌嗪咪唑脲类化合物的用途，其特征在于式Ⅰ化合物用作农用杀菌剂，其单一使用或与另外的生物活性化合物的组合使用，对农业或林业菌害有防治效果。
3.一种杀菌组合物，含有权利要求1所述的式Ⅰ化合物为活性组分和农业或林业上可接受的载体。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810668834.8A CN108675991B (zh) | 2018-06-25 | 2018-06-25 | 一种含氟吡啶哌嗪咪唑脲及其应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810668834.8A CN108675991B (zh) | 2018-06-25 | 2018-06-25 | 一种含氟吡啶哌嗪咪唑脲及其应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108675991A true CN108675991A (zh) | 2018-10-19 |
| CN108675991B CN108675991B (zh) | 2020-11-03 |
Family
ID=63812364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810668834.8A Active CN108675991B (zh) | 2018-06-25 | 2018-06-25 | 一种含氟吡啶哌嗪咪唑脲及其应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108675991B (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130072497A1 (en) * | 2005-06-30 | 2013-03-21 | Dow Agrosciences Llc | N- substituted piperazines |
| CN104418800A (zh) * | 2013-09-06 | 2015-03-18 | 中国中化股份有限公司 | 芳基吡(嘧)啶类化合物及其用途 |
| CN107827815A (zh) * | 2017-11-10 | 2018-03-23 | 西南大学 | 氟喹诺酮类氨基衍生物及其防治柑橘病害的用途 |
-
2018
- 2018-06-25 CN CN201810668834.8A patent/CN108675991B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130072497A1 (en) * | 2005-06-30 | 2013-03-21 | Dow Agrosciences Llc | N- substituted piperazines |
| CN104418800A (zh) * | 2013-09-06 | 2015-03-18 | 中国中化股份有限公司 | 芳基吡(嘧)啶类化合物及其用途 |
| CN107827815A (zh) * | 2017-11-10 | 2018-03-23 | 西南大学 | 氟喹诺酮类氨基衍生物及其防治柑橘病害的用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108675991B (zh) | 2020-11-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW200911753A (en) | Novel fungicides | |
| CN108477170A (zh) | 一种喹啉类化合物及其制备方法和在防治植物病害中的用途 | |
| JPS609748B2 (ja) | １、２−ジクロロシアノビニル化合物及び微生物抑制剤としての利用 | |
| CN109503562A (zh) | 2-[4-(2-噻吩基)]嘧啶基脲衍生物及其制备方法和应用 | |
| CN105601638B (zh) | 一种叶绿酸衍生物及其制备方法、作为光敏抑菌剂及光敏杀虫剂的应用 | |
| CN109897012A (zh) | 一种具有杀菌活性的噻霉酮配合物及其制备方法和应用 | |
| CN109942561A (zh) | 4-(2-噻吩基)嘧啶衍生物及其制备方法和应用 | |
| CN102633805B (zh) | 白屈菜红碱醇化物及其制备方法和在植物杀菌剂药物中的应用 | |
| CN106946770A (zh) | 高活性亚胺基苯乙酸酯类化合物及其制备方法和应用 | |
| CN104926725B (zh) | 一种萘二甲酰亚胺芳基脲类化合物及其用途 | |
| CN108675991A (zh) | 一种含氟吡啶哌嗪咪唑脲及其应用 | |
| CN100515200C (zh) | 硝酸钕小檗碱配合物农药杀菌乳剂及其制备方法 | |
| CN108794462A (zh) | 一种含氟氰亚胺噻唑烷取代的噁二唑类杀虫杀菌剂 | |
| CN108640871A (zh) | 一种含氟吡啶哌嗪脲类化合物及其应用 | |
| CN114805244A (zh) | 双-(1,3,4-噻二唑)类衍生物及其制备方法和应用 | |
| CN107494553A (zh) | 一种没食子酸衍生的农用杀菌剂及用途 | |
| CN100515201C (zh) | 硝酸钐小檗碱配合物农药杀菌乳剂及其制备方法 | |
| CN103788119A (zh) | 噻二唑类金属络合物及其在防治农业植物病害中的应用 | |
| CN109535136A (zh) | 2-[4-(2-呋喃基)]嘧啶基脲类化合物及其制备方法和应用 | |
| CN105669973A (zh) | 一种具抑菌活性的化合物及其制备和应用 | |
| Nazir et al. | Synthesis of promising antibacterial and antifungal agents: 2-[[(4-Chlorophenyl) sulfonyl](2, 3-dihydro-1, 4-benzodioxin-6-yl) amino]-N-(un/substituted-phenyl) acetamides | |
| CN106800534B (zh) | 一种肉桂酸萘二甲酰亚胺酯类化合物及其用途 | |
| CN100515202C (zh) | 硝酸钆小檗碱配合物农药杀菌乳剂及其制备方法 | |
| CN108484443A (zh) | 一种具有抗菌活性的氰氟酰胺化合物及其制备方法和应用 | |
| CN103554026A (zh) | 一组3-三氟甲基-4-甲酰吡唑化合物 |
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 |