CN100387595C - 一种含苯并三唑的三唑有机化合物、制备方法及应用 - Google Patents
一种含苯并三唑的三唑有机化合物、制备方法及应用 Download PDFInfo
- Publication number
- CN100387595C CN100387595C CNB2005101044807A CN200510104480A CN100387595C CN 100387595 C CN100387595 C CN 100387595C CN B2005101044807 A CNB2005101044807 A CN B2005101044807A CN 200510104480 A CN200510104480 A CN 200510104480A CN 100387595 C CN100387595 C CN 100387595C
- Authority
- CN
- China
- Prior art keywords
- bromo
- compound
- triazole
- reaction
- methyl phenyl
- 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
- -1 triazole organic compounds Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 6
- 239000012964 benzotriazole Substances 0.000 title abstract description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000001875 compounds Chemical group 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 3
- 239000005648 plant growth regulator Substances 0.000 claims abstract 2
- 239000002585 base Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- AHAYUDFIDBKIPU-UHFFFAOYSA-N C1=CC=C(C=C1)C(=O)CC2=C(C=C(C=C2)Br)Br Chemical compound C1=CC=C(C=C1)C(=O)CC2=C(C=C(C=C2)Br)Br AHAYUDFIDBKIPU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- GPTAKAWFMITEOL-UHFFFAOYSA-N 2-(4-bromophenyl)-1-phenylethanone Chemical compound C1=CC(Br)=CC=C1CC(=O)C1=CC=CC=C1 GPTAKAWFMITEOL-UHFFFAOYSA-N 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 230000001954 sterilising effect Effects 0.000 abstract description 4
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract 3
- 239000003899 bactericide agent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000013329 compounding Methods 0.000 abstract 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 244000003416 Asparagus officinalis Species 0.000 description 2
- 235000005340 Asparagus officinalis Nutrition 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000005846 Triadimenol Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 241000198596 Alternaria tomatophila Species 0.000 description 1
- URDNHJIVMYZFRT-UHFFFAOYSA-N Diclobutrazol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)CC1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 239000005985 Paclobutrazol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000009266 disease activity Effects 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QHMWCHQXCUNUAK-UHFFFAOYSA-N flutrimazole Chemical compound C1=CC(F)=CC=C1C(N1C=NC=C1)(C=1C(=CC=CC=1)F)C1=CC=CC=C1 QHMWCHQXCUNUAK-UHFFFAOYSA-N 0.000 description 1
- 229960000690 flutrimazole Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940061584 phosphoramidic acid Drugs 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种含苯并三唑的新三唑有机化合物:2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮、制备及应用。其制备方法的特征为:以4-溴苯基苯乙酮为原料,碱为敷酸剂,合成2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮。溶剂为丙酮、氯仿。反应温度为0~40℃。所用敷酸剂碱为三乙胺、吡啶、碳酸钾、碳酸钠。本发明还涉及该化合物的用途,该化合物具有较高的植物生长调节活性和一定的杀菌功能,可以用于混配杀菌剂中,而这种混配杀菌剂可广泛应用于防治多种植物的病害和促进植物生长,为制备新的植物生长调节剂提供了一类新的化合物。
Description
技术领域
本发明涉及新颖的苯并三唑有机化合物;其制备方法;以该化合物为活性成份的组合物在调节植物生长性能、杀菌中的应用。
背景技术
近年来杂环化合物在农药中占据着十分重要的位置,由于它的低毒性赋予了化学农药新的生命,有利于解决农药和化学防治所面临的“效力、效率、环境”相互关系的难题。使农药进入到一个超高效无公害的新纪元。在这种变化中,特别是含氮杂环化合物,如吡啶、嘧啶、吡唑、三氮唑及稠杂环等是近年发展最为活跃的领域。到目前为止,其中最重要,品种也最多的是三唑化合物。已经问世并商品化的三唑类化合物有西德拜耳公司的氟三唑(Persulor)、三唑酮(Bayleton)、三唑醇(Triadimenol),比利时Jenssen公司的乙环唑(Etaconazole)、丙环唑(Propiconaxole)、英国CIC公司的多效唑(PP333)、苄氯三唑醇(Diclo-Butrazole),日本住友化学公司的S-3307(Petefezol)、S-3308(Penteconaxol)。由于内吸性杀菌剂可以治疗一些侵染到植物体内的病害,且容易被茎叶根吸收,同时受环境的影响较小。此外,内吸性杀菌剂对病害的选择性较强,疗效较高。缺点是容易产生抗药性。因此解决植物抗药性问题,在原有品种基础上引入新型官能团,进行官能团修饰,合成具有高效、广谱、低毒、低抗性、双效性(杀菌、控长)特点的杀菌剂是当前有机化学领域的一个重要任务。
发明内容
本发明的目的是提供一种新的具有高效、低毒、双效性(杀菌、控长)的三唑有机化合物,本发明的另一目的是提供一种合成本发明化合物的方法及本发明化合物的用途。
本发明新三唑有机化合物的结构式为:
本发明的化合物是通过有机合成技术制备的,合成该化合物的方法包括以下步骤:
1)2-溴-1-(4-溴-苯基)苯乙酮的制备
采用《许良忠,合成化学,含三氮唑的硫代(或二硫代)氨基磷酸酯类衍生物研究,1997,5(3),277页》合成方法制备2-溴-1-(2,4-二氯)苯乙酮。
2)1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮的制备
合成方法同步骤1同一文献中
3)2-卤-1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮的制备
合成方法同步骤1同一文献中
4)2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮的合成
以碱为敷酸剂,合成2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮。溶剂为丙酮、氯仿。反应温度为0~40℃。所用敷酸剂碱为三乙胺、吡啶、碳酸钾、碳酸钠。
发明人发现本发明化合物具有化学性质稳定、广谱活性和优异的植物生长调节性等优点,是农用杀菌剂的理想组成成分。
实施例
以下的具体实例可以使本专业的技术人员更全面的理解本发明,并不是对本发明的限定。
实施例1:
1)2-溴-1-(4-溴-苯基)苯乙酮的制备
将57.8g 4-溴苯基苯乙酮溶于90mL无水乙醚,冰盐浴冷却至0℃以下,搅拌滴加32.0g液溴,控制滴加速度,约2h滴完。维持反应温度继续反应至颜色褪去,停止反应。将反应液倒入500mL分液漏斗中,用冰水洗涤至有机相成中性,用无水MgSO4干燥过夜。粗品为淡黄色固体,用1∶1的乙醇和水重结晶得白色片状晶体2-溴-1-(4-溴-苯基)苯乙酮。
2)1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮
将53.1g 2-溴-1-(4-溴-苯基)苯乙酮、11.4g 1H-1,2,4-三氮唑溶于100mL丙酮,0℃左右搅拌滴加23.3mL三乙胺,约1h滴完。随着三乙胺的滴入,有大量白色针状物析出,滴完继续在室温下搅拌1h左右,结束反应。将反应液倾入水中,静置过夜,过滤得白色固体,用乙醇重结晶得白色片状晶体1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮。
3)2-溴-1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮的制备
将34.2g 1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮、8.2g无水醋酸钠及100mL冰乙酸在室温下混合均匀,搅拌滴加16.0g液溴,控制滴加速度,约2h滴完。维持反应温度继续搅拌至颜色褪去,停止反应。将反应液倒入250mL分液漏斗中,加入50mL氯仿,先用水洗,再用NaHCO3水溶液、水反复洗至有机相成中性,用无水MgSO4干燥,在容量瓶中配成100mL氯仿溶液,供下步反应使用。
4)2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮的合成
将1.8g苯并三唑溶于10mL丙酮,冰浴,缓慢滴加约含4.2g 2-溴-1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮的氯仿溶液,约0.5h滴加完毕。再将2.1mL三乙胺加入恒压滴液漏斗中缓慢加到反应瓶中,滴加完毕后撤去冰浴,升温至20℃反应3h。反应完后,旋蒸除去溶剂,再倒入盛100mL水的250mL烧杯中,充分搅拌,用氯仿萃取,取氯仿层旋蒸。经硅胶柱分离(淋洗剂,乙酸乙酯∶石油醚=1∶3),得2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮,其形状为白色固体。
实施例2:
步骤1)--3)同实施例1
4)将1.8g苯并三唑溶于10mL氯仿,冰浴下缓慢滴加约含4.2g 2-溴-1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮的氯仿溶液,约0.5h滴加完毕。再将1.2g的吡啶加入恒压滴液漏斗中缓慢加到反应瓶中,滴加完毕后,升温至40℃反应3h。反应完后,旋蒸除去溶剂,再倒入盛有100mL水的250mL烧杯中,充分搅拌,用氯仿萃取,取氯仿层旋蒸。经硅胶柱分离(淋洗剂,乙酸乙酯∶石油醚=1∶3),得2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮,其形状为白色固体。如果淋洗剂自然挥发,得到的目的产物为无色柱状晶体。
通过IR、1H NMR和X-射线衍射方法对所合成的化合物进行表征,以确认其结构。
IR(红外光谱):
羰基(C=O键伸缩振动,1704cm-1)
碳氮双键(C=N键伸缩振动,1507cm-1)
碳氮单键(C-N-C伸缩振动,955cm-1)
1H NMR(核磁共振氢谱):
δ=7.45×10-6~8.09×10-6为质子1、2、3、4、6、7、8、9、12、13、14、15;δ=7.46×10-6为质子5;δ=8.59×10-6和8.68×10-6为质子10和11。
X-ray(X-射线衍射):
X-射线衍射分析表明化合物为2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮。其结构式为:
由此确认所合成的化合物的结构与预期一致。
发明效果
用本发明化合物在南开大学元素有机所对植物的各种菌病害进行了试验,实验方法为离体平皿法。
测试结果如下:
1.在50ppm的浓度下,2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)苯乙酮对小麦赤霉病害活性为44.2%,对番茄早疫病害的杀菌活性达到41.3%,对花生褐斑的活性,37.1%,对芦笋茎枯,38.5%,而对苹果轮纹病害,则在54.5%。
2.500ppm时,化合物对小麦赤霉、番茄早疫、花生褐斑、苹果轮纹及芦笋茎枯的活性均超过100%。
3.用本发明化合物在南开大学元素有机所对黄瓜生根进行了试验,实验方法为离体黄瓜子叶生根法。测试结果如下:10ppm时其活性高达160%。
以上试验证明本发明化合物具有优异的杀菌性能和植物生长调节活性,可独立或作为活性成份在农用杀菌剂中应用。
Claims (5)
2.按照权利要求1的化合物的制备方法,该方法包括以下步骤:
1)以无水乙醚为溶剂,使4-溴苯基苯乙酮与液溴反应制备2-溴-1-(4-溴-苯基)苯乙酮;
2)在有机溶剂介质中,以碱为敷酸剂,合成1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮,反应温度为0~40℃;
3)反应完毕后,在酸性溶剂中通过取代反应合成2-卤-1-(4-溴-苯基)-2-(1H-1,2,4-三唑-1-基)苯乙酮,反应温度为0~60℃;
4)在有机溶剂介质中,以碱为敷酸剂,合成2-(1-H-苯并[1,2,3]三唑-1基)-1-(4-溴-苯基)-2-(1H-1,2,4三唑-1基)-苯乙酮,溶剂为丙酮或氯仿,反应温度为0~40℃。
3.按照权利要求2的制备方法,其所述碱指的是三乙胺或吡啶或碳酸钠或碳酸钾。
4.含有权利要求1所述化合物的植物生长调节剂。
5.含有权利要求1所述化合物的混配杀菌剂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005101044807A CN100387595C (zh) | 2005-11-07 | 2005-11-07 | 一种含苯并三唑的三唑有机化合物、制备方法及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005101044807A CN100387595C (zh) | 2005-11-07 | 2005-11-07 | 一种含苯并三唑的三唑有机化合物、制备方法及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1775777A CN1775777A (zh) | 2006-05-24 |
CN100387595C true CN100387595C (zh) | 2008-05-14 |
Family
ID=36765514
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2005101044807A Expired - Fee Related CN100387595C (zh) | 2005-11-07 | 2005-11-07 | 一种含苯并三唑的三唑有机化合物、制备方法及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100387595C (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0447921A2 (en) * | 1990-03-12 | 1991-09-25 | Fuji Photo Film Co., Ltd. | Silver halide colour photographic material |
US6172092B1 (en) * | 1995-06-28 | 2001-01-09 | Bayer Aktiengesellschaft | Microbicidal benzotriazoles |
JP2003524620A (ja) * | 1999-03-24 | 2003-08-19 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環化合物 |
-
2005
- 2005-11-07 CN CNB2005101044807A patent/CN100387595C/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0447921A2 (en) * | 1990-03-12 | 1991-09-25 | Fuji Photo Film Co., Ltd. | Silver halide colour photographic material |
US6172092B1 (en) * | 1995-06-28 | 2001-01-09 | Bayer Aktiengesellschaft | Microbicidal benzotriazoles |
JP2003524620A (ja) * | 1999-03-24 | 2003-08-19 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環化合物 |
Non-Patent Citations (2)
Title |
---|
2-(1H-Benzotriazol-1-yl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone. Jun Wan et al.Acta Crystallographica Section E,Vol.61 No.10. 2005 |
2-(1H-Benzotriazol-1-yl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone. Jun Wan et al.Acta Crystallographica Section E,Vol.61 No.10. 2005 * |
Also Published As
Publication number | Publication date |
---|---|
CN1775777A (zh) | 2006-05-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2319697C2 (ru) | Дифторметилтиазолилкарбоксанилиды | |
AU2010329332B2 (en) | Azole derivatives, methods for producing the same, intermediate thereof, agro-horticultural agents | |
JPS5962576A (ja) | トリアゾリル−アルカノ−ルおよびこれらの塩の製造方法 | |
EP0071568B1 (de) | Mandelsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Mikroorganismen | |
CN101225074A (zh) | 一类含芳醚三氮唑化合物的合成及杀菌活性 | |
CA1212952A (en) | 1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides | |
CS215063B2 (en) | Fungicide means and means for suppressing the non-desirable plant growth | |
NO802616L (no) | Acylerte triazolyl-gamma-fluorpinakolyl-derivater, fremgangsmaate til deres fremstilling og deres anvendelse som fungicider | |
HU192005B (en) | Fungicide composition and process for preparing azolyl-3-pyrazolyl-2-propanol derivatives | |
KR20020067611A (ko) | 이소티아졸카복실산 유도체 및 살미생물제로서의 그의 용도 | |
CN100387595C (zh) | 一种含苯并三唑的三唑有机化合物、制备方法及应用 | |
EP0272895B1 (en) | Novel azole derivative, method for production thereof, and agricultural/horticultural fungicide containing said derivative as active ingredient | |
CS212719B2 (en) | Fungicide | |
CN104876916A (zh) | 苯醚甲环唑的制备方法 | |
SU1313347A3 (ru) | Способ получени производных триазола | |
HU189678B (en) | Fungicide and plant growth regulating compositions containing alkyl-azole derivatives as active substances | |
DE3021551A1 (de) | 4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
CN104628646B (zh) | N‑吡唑基甲酰苯胺类化合物、中间体、组合物、制备方法及应用 | |
CN1763037A (zh) | 一种新颖的三唑有机化合物、制备方法及应用 | |
CN1763038A (zh) | 一种新颖的苯骈三氮唑有机化合物、制备方法及应用 | |
EA007384B1 (ru) | Кристаллическая модификация ii 2-[2-(1-хлорциклопропил)-3-(2-хлорфенил)-2-гидроксипропил]-2,4-дигидро-3н-1,2,4-триазол-3-тиона | |
US11524934B2 (en) | Phenylamine compounds | |
JPS61271276A (ja) | ジクロロシクロプロピルアルキル−ヒドロキシアルキル−アゾ−ル誘導体 | |
EP1074546B1 (en) | 5-iodo-4-phenethylaminopyrimidine derivatives, intermediates thereof, process for producing the same and agricultural/horticultural pesticides | |
CN110357857A (zh) | 吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |