CN101874485A - 一种双酰肼类化合物作为杀菌剂的应用 - Google Patents
一种双酰肼类化合物作为杀菌剂的应用 Download PDFInfo
- Publication number
- CN101874485A CN101874485A CN2010102136741A CN201010213674A CN101874485A CN 101874485 A CN101874485 A CN 101874485A CN 2010102136741 A CN2010102136741 A CN 2010102136741A CN 201010213674 A CN201010213674 A CN 201010213674A CN 101874485 A CN101874485 A CN 101874485A
- Authority
- CN
- China
- Prior art keywords
- chlorphenyl
- phenyl
- cucumber
- formula
- dichlorophenoxy
- 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
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 31
- 239000003899 bactericide agent Substances 0.000 title claims abstract description 27
- 125000005077 diacylhydrazine group Chemical group 0.000 title abstract 3
- 240000008067 Cucumis sativus Species 0.000 claims abstract description 42
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims abstract description 41
- 241000395107 Cladosporium cucumerinum Species 0.000 claims abstract description 10
- 241000221785 Erysiphales Species 0.000 claims abstract description 10
- -1 pyridine radicals Chemical group 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 16
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 claims description 15
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 241000221775 Hypocreales Species 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 abstract 1
- 241000221662 Sclerotinia Species 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 23
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- CEDZFAONRDZJKJ-UHFFFAOYSA-N [O].ClC1=CC=CC(=C1)Cl Chemical compound [O].ClC1=CC=CC(=C1)Cl CEDZFAONRDZJKJ-UHFFFAOYSA-N 0.000 description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001263 acyl chlorides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002255 vaccination Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- STVWDDZUEVJZKZ-UHFFFAOYSA-N C(CC)(=O)O.[O].ClC1=CC=CC(=C1)Cl Chemical compound C(CC)(=O)O.[O].ClC1=CC=CC(=C1)Cl STVWDDZUEVJZKZ-UHFFFAOYSA-N 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 241000609455 Corynespora cassiicola Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
产物编号 | 酰氯类化合物RCOCl中的R | |
实施例2 | Va | 苯基 |
实施例3 | Vb | 4-硝基苯基 |
实施例4 | Vc | 4-氯苯基 |
实施例5 | Vd | 4-氟苯基 |
实施例6 | Ve | 3-甲基苯基 |
实施例7 | Vf | 3-氯苯基 |
实施例8 | Vg | 2-氯苯基 |
实施例9 | Vh | 2,4-二氯苯基 |
实施例10 | Vi | 2-甲氧基苯基 |
实施例11 | Vj | 4-甲氧基苯基 |
实施例12 | Vk | 异噁唑基 |
实施例13 | Vl | 1-氰基-1-环丙基 |
实施例14 | Vm | 乙基 |
实施例15 | Vn | 异丙基 |
实施例16 | Vo | 苯甲基 |
实施例1 | Vp | 环丙基 |
实施例17 | Vq | 2,4-二氯苯氧甲基 |
实施例18 | Vr | 2,4-二氯苯氧丙基 |
实施例19 | Vs | 4-碘苯基 |
实施例20 | Vt | 3-吡啶基 |
实施例21 | Vu | 4-吡啶基 |
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010213674 CN101874485B (zh) | 2010-06-30 | 2010-06-30 | 一种双酰肼类化合物作为杀菌剂的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010213674 CN101874485B (zh) | 2010-06-30 | 2010-06-30 | 一种双酰肼类化合物作为杀菌剂的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101874485A true CN101874485A (zh) | 2010-11-03 |
CN101874485B CN101874485B (zh) | 2013-04-24 |
Family
ID=43017251
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201010213674 Expired - Fee Related CN101874485B (zh) | 2010-06-30 | 2010-06-30 | 一种双酰肼类化合物作为杀菌剂的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101874485B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102860305A (zh) * | 2012-09-14 | 2013-01-09 | 浙江工业大学 | 一种含2,4-二氯苯氧乙酰基双酰肼类化合物作为杀菌剂的应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006081759A1 (fr) * | 2005-02-06 | 2006-08-10 | Shenyang Research Institute Of Chemical Industry | N-méthoxycarbamates n-substitués par des groupements phényle 2-substitués, leur synthèse et leurs applications |
CN101223891A (zh) * | 2008-01-25 | 2008-07-23 | 中国农业大学 | 用于抑制植物病原真菌的八角精油及其制备方法 |
CN101289422A (zh) * | 2008-06-06 | 2008-10-22 | 华中师范大学 | 具有杀菌、除草活性的2,3,5,6-四取代-4-氨基吡啶及制备 |
-
2010
- 2010-06-30 CN CN 201010213674 patent/CN101874485B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006081759A1 (fr) * | 2005-02-06 | 2006-08-10 | Shenyang Research Institute Of Chemical Industry | N-méthoxycarbamates n-substitués par des groupements phényle 2-substitués, leur synthèse et leurs applications |
CN101223891A (zh) * | 2008-01-25 | 2008-07-23 | 中国农业大学 | 用于抑制植物病原真菌的八角精油及其制备方法 |
CN101289422A (zh) * | 2008-06-06 | 2008-10-22 | 华中师范大学 | 具有杀菌、除草活性的2,3,5,6-四取代-4-氨基吡啶及制备 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102860305A (zh) * | 2012-09-14 | 2013-01-09 | 浙江工业大学 | 一种含2,4-二氯苯氧乙酰基双酰肼类化合物作为杀菌剂的应用 |
Also Published As
Publication number | Publication date |
---|---|
CN101874485B (zh) | 2013-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69324552T4 (de) | N'-substituierte-N,N'Diacylhydrazin-Insektizide | |
CN104693035B (zh) | 水杨酸类反‑(β)‑法尼烯类似物及其应用 | |
CN101889577B (zh) | 一种双酰肼类化合物作为除草剂的应用 | |
CN109928929A (zh) | 吡唑酰胺类化合物及其应用和杀菌剂 | |
WO2021147484A1 (zh) | 一种用于小麦全蚀病病菌抑制的2-(1,2,4-三氮唑)苯甲酰芳胺类活性化合物 | |
WO1987003591A1 (en) | Novel imidazole derivatives, bactericides containing them, and process for their preparation | |
CN103214461B (zh) | 一种喹啉衍生物及其用途 | |
CN111253400B (zh) | 一类具有杀虫活性的卤代吡唑苦参碱衍生物及制备方法和应用 | |
CN105037350A (zh) | 一种骆驼蓬碱类化合物及其在防治荔枝霜疫霉病方面的应用 | |
CN101874485B (zh) | 一种双酰肼类化合物作为杀菌剂的应用 | |
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 | |
CN109956904B (zh) | 吡唑酰胺类化合物及其应用和杀菌剂 | |
CN102860305A (zh) | 一种含2,4-二氯苯氧乙酰基双酰肼类化合物作为杀菌剂的应用 | |
CN101889576B (zh) | 一种双酰肼类化合物作为植物生长调节剂的应用 | |
CN114805219B (zh) | 一种含氟嘧啶双醚类化合物及其用途 | |
CN102835394A (zh) | 一种含2,4-二氯苯氧乙酰基双酰肼类化合物作为除草剂的应用 | |
DE2525855A1 (de) | Verfahren zum erzeugen von benzanilidderivaten | |
DE2802282A1 (de) | Substituierte cycloalkancarbonsaeureanilide, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
CN100369911C (zh) | 井冈羟胺a-4,7,4’,7’-二缩醛或酮类化合物及其制备与应用 | |
CN107721997B (zh) | 噻二唑类噻唑啉酮化合物及其制备方法和应用 | |
DE2139042A1 (de) | Dipyridylaminverbindungen, Verfahren zu deren Herstellung und deren Verwendung | |
CN101735199B (zh) | 邻甲酰胺基苯甲酰吡唑类化合物及其制备方法和应用 | |
CN104557691B (zh) | 一种3‑胺酰双酰肼衍生物及其制备方法和应用 | |
CN114644596B (zh) | 一种含氟嘧啶芳胺类化合物及其用途 | |
DE2545569B2 (de) | 1,3-dithiacyclopenten-2-ylidenmalonsaeuredialkylester, verfahren zu deren herstellung und diese enthaltende fungizide mittel |
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 | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200803 Address after: 215008 Room 202, No. 10-4, oil truck farm, Gusu District, Suzhou City, Jiangsu Province Patentee after: Guan Yan Address before: Room 601, building 9, No. 568, Jinyang East Road, Luoxing street, Jiashan County, Hangzhou City, Zhejiang Province Patentee before: Jiashan talent technology transformation service center Effective date of registration: 20200803 Address after: Room 601, building 9, No. 568, Jinyang East Road, Luoxing street, Jiashan County, Hangzhou City, Zhejiang Province Patentee after: Jiashan talent technology transformation service center Address before: Hangzhou City, Zhejiang province 310014 City Zhaohui District Six Patentee before: ZHEJIANG University OF TECHNOLOGY |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200902 Address after: 314100 floor 1, C7, No. 555 Chuangye Road, Dayun Town, Jiashan County, Jiaxing City, Zhejiang Province Patentee after: Jiasheng biomedical (Jiaxing) Co.,Ltd. Address before: 215008 Room 202, No. 10-4, oil truck farm, Gusu District, Suzhou City, Jiangsu Province Patentee before: Guan Yan |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130424 |