DE2003562A1 - Neue Phosphorderivate,ihre Herstellung und die diese Verbindungen enthaltenden Mittel - Google Patents
Neue Phosphorderivate,ihre Herstellung und die diese Verbindungen enthaltenden MittelInfo
- Publication number
- DE2003562A1 DE2003562A1 DE19702003562 DE2003562A DE2003562A1 DE 2003562 A1 DE2003562 A1 DE 2003562A1 DE 19702003562 DE19702003562 DE 19702003562 DE 2003562 A DE2003562 A DE 2003562A DE 2003562 A1 DE2003562 A1 DE 2003562A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- general formula
- preparation
- phosphorus derivatives
- compounds
- 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
- 239000000203 mixture Substances 0.000 title claims description 12
- 150000003017 phosphorus Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 title claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000749 insecticidal effect Effects 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002473 indoazoles Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- REHRQXVEAXFIML-UHFFFAOYSA-N 1h-indazole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=NNC2=C1 REHRQXVEAXFIML-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- QMIBICADHKQAJK-UHFFFAOYSA-N 5-chloro-1h-indazole-3-carbonitrile Chemical compound ClC1=CC=C2NN=C(C#N)C2=C1 QMIBICADHKQAJK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000299906 Cucumis sativus var. sativus Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003218 pyrazolidines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
- C07F9/65038—Five-membered rings having the nitrogen atoms in the positions 1 and 2 condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6901549A FR2029387A1 (en) | 1969-01-27 | 1969-01-27 | Diethyl esters of 3,4-subst-1h-indazol-1-yl- - thiophosphorous acids |
| FR6936237A FR2066881A6 (en) | 1969-10-22 | 1969-10-22 | Diethyl esters of 3,4-subst-1h-indazol-1-yl- - thiophosphorous acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2003562A1 true DE2003562A1 (de) | 1970-08-27 |
Family
ID=26214804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702003562 Pending DE2003562A1 (de) | 1969-01-27 | 1970-01-27 | Neue Phosphorderivate,ihre Herstellung und die diese Verbindungen enthaltenden Mittel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3763180A (en, 2012) |
| JP (1) | JPS4915775B1 (en, 2012) |
| AT (1) | AT299613B (en, 2012) |
| BE (1) | BE744961A (en, 2012) |
| CA (1) | CA931964A (en, 2012) |
| CH (1) | CH507656A (en, 2012) |
| DE (1) | DE2003562A1 (en, 2012) |
| DK (1) | DK126206B (en, 2012) |
| ES (1) | ES375926A1 (en, 2012) |
| GB (1) | GB1252111A (en, 2012) |
| IL (1) | IL33780A (en, 2012) |
| LU (1) | LU60227A1 (en, 2012) |
| NL (1) | NL7000716A (en, 2012) |
| OA (1) | OA03406A (en, 2012) |
| SE (1) | SE360082B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994890A (en) * | 1974-01-31 | 1976-11-30 | Chugai Seiyaku Kabushiki Kaisha | 1-Aminoalkyl, 3-phenyl indazoles |
-
1970
- 1970-01-19 NL NL7000716A patent/NL7000716A/xx unknown
- 1970-01-20 OA OA53838A patent/OA03406A/xx unknown
- 1970-01-23 US US00005347A patent/US3763180A/en not_active Expired - Lifetime
- 1970-01-23 JP JP45005765A patent/JPS4915775B1/ja active Pending
- 1970-01-23 CA CA073012A patent/CA931964A/en not_active Expired
- 1970-01-23 GB GB1252111D patent/GB1252111A/en not_active Expired
- 1970-01-26 IL IL33780A patent/IL33780A/xx unknown
- 1970-01-26 BE BE744961D patent/BE744961A/xx unknown
- 1970-01-26 DK DK35170AA patent/DK126206B/da unknown
- 1970-01-26 SE SE00938/70A patent/SE360082B/xx unknown
- 1970-01-26 CH CH104470A patent/CH507656A/fr not_active IP Right Cessation
- 1970-01-26 LU LU60227D patent/LU60227A1/xx unknown
- 1970-01-27 ES ES375926A patent/ES375926A1/es not_active Expired
- 1970-01-27 AT AT72870A patent/AT299613B/de not_active IP Right Cessation
- 1970-01-27 DE DE19702003562 patent/DE2003562A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7000716A (en, 2012) | 1970-07-29 |
| IL33780A (en) | 1972-09-28 |
| LU60227A1 (en, 2012) | 1970-07-29 |
| CH507656A (fr) | 1971-05-31 |
| SE360082B (en, 2012) | 1973-09-17 |
| OA03406A (fr) | 1970-12-15 |
| US3763180A (en) | 1973-10-02 |
| BE744961A (fr) | 1970-07-27 |
| CA931964A (en) | 1973-08-14 |
| GB1252111A (en, 2012) | 1971-11-03 |
| DK126206B (da) | 1973-06-18 |
| ES375926A1 (es) | 1972-07-01 |
| IL33780A0 (en) | 1970-03-22 |
| AT299613B (de) | 1972-06-26 |
| JPS4915775B1 (en, 2012) | 1974-04-17 |
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