DE1900125C3 - Substituierte Pyrazolone, Verfahren zu ihrer Herstellung und fungizide Zusammensetzungen - Google Patents
Substituierte Pyrazolone, Verfahren zu ihrer Herstellung und fungizide ZusammensetzungenInfo
- Publication number
- DE1900125C3 DE1900125C3 DE1900125A DE1900125A DE1900125C3 DE 1900125 C3 DE1900125 C3 DE 1900125C3 DE 1900125 A DE1900125 A DE 1900125A DE 1900125 A DE1900125 A DE 1900125A DE 1900125 C3 DE1900125 C3 DE 1900125C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- pyrazolone
- product
- dichloro
- 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
Links
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title claims description 6
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 title claims 3
- 238000000034 method Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 title description 4
- 230000000855 fungicidal effect Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl cyanoacetate Chemical compound 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 4
- 229920000940 maneb Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- MVFUINRKRLOOMK-UHFFFAOYSA-N 5-amino-4,4-dichloro-2-(4-chlorophenyl)pyrazol-3-one Chemical compound ClC1=CC=C(C=C1)N1N=C(C(C1=O)(Cl)Cl)N MVFUINRKRLOOMK-UHFFFAOYSA-N 0.000 description 3
- SHMKFIUSVJKDSQ-UHFFFAOYSA-N 5-amino-4,4-dichloro-2-[3-(trifluoromethyl)phenyl]pyrazol-3-one Chemical compound FC(C=1C=C(C=CC1)N1N=C(C(C1=O)(Cl)Cl)N)(F)F SHMKFIUSVJKDSQ-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000221779 Fusarium sambucinum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- JSWQDLBFVSTSIW-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC=C1C(F)(F)F JSWQDLBFVSTSIW-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000015190 carrot juice Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001534756 Mungos Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000906064 Zeus faber Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012871 anti-fungal composition Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR134865 | 1968-01-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1900125A1 DE1900125A1 (de) | 1969-09-04 |
| DE1900125B2 DE1900125B2 (de) | 1979-04-05 |
| DE1900125C3 true DE1900125C3 (de) | 1979-11-29 |
Family
ID=8644137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1900125A Expired DE1900125C3 (de) | 1968-01-04 | 1969-01-02 | Substituierte Pyrazolone, Verfahren zu ihrer Herstellung und fungizide Zusammensetzungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3632818A (en:Method) |
| BE (1) | BE725968A (en:Method) |
| DE (1) | DE1900125C3 (en:Method) |
| FR (1) | FR1558513A (en:Method) |
| GB (1) | GB1229141A (en:Method) |
| LU (1) | LU57694A1 (en:Method) |
| NL (1) | NL160816C (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1653967B1 (de) * | 1967-04-25 | 1971-04-22 | Engstfeld Wilh Fa | Druecker-Dornverbindung |
| US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| US3950528A (en) * | 1972-06-23 | 1976-04-13 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| DE2319278C2 (de) * | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmazeutisches Mittel |
| US3992404A (en) * | 1973-04-17 | 1976-11-16 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4045571A (en) * | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4000294A (en) * | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4056533A (en) * | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4069334A (en) * | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| DE2427272C3 (de) * | 1974-06-06 | 1981-10-01 | Bayer Ag, 5090 Leverkusen | 1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum |
| DE3027845A1 (de) * | 1980-07-23 | 1982-02-25 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-on |
| US4436717A (en) | 1981-05-29 | 1984-03-13 | The United States Of America As Represented By The United States Department Of Energy | 18 F-4-Fluoroantipyrine |
-
1968
- 1968-01-04 FR FR134865A patent/FR1558513A/fr not_active Expired
- 1968-12-23 BE BE725968D patent/BE725968A/xx unknown
- 1968-12-27 LU LU57694D patent/LU57694A1/xx unknown
-
1969
- 1969-01-02 US US788629A patent/US3632818A/en not_active Expired - Lifetime
- 1969-01-02 DE DE1900125A patent/DE1900125C3/de not_active Expired
- 1969-01-03 NL NL6900067.A patent/NL160816C/xx not_active IP Right Cessation
- 1969-01-06 GB GB1229141D patent/GB1229141A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU57694A1 (en:Method) | 1969-04-21 |
| US3632818A (en) | 1972-01-04 |
| BE725968A (en:Method) | 1969-06-23 |
| GB1229141A (en:Method) | 1971-04-21 |
| DE1900125B2 (de) | 1979-04-05 |
| DE1900125A1 (de) | 1969-09-04 |
| FR1558513A (en:Method) | 1969-02-28 |
| NL160816B (nl) | 1979-07-16 |
| NL6900067A (en:Method) | 1969-07-08 |
| NL160816C (nl) | 1979-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |