CH485773A - Verfahren zur Herstellung neuer (Thio-)Phosphorsäureester bzw. -amide - Google Patents
Verfahren zur Herstellung neuer (Thio-)Phosphorsäureester bzw. -amideInfo
- Publication number
- CH485773A CH485773A CH413469A CH413469A CH485773A CH 485773 A CH485773 A CH 485773A CH 413469 A CH413469 A CH 413469A CH 413469 A CH413469 A CH 413469A CH 485773 A CH485773 A CH 485773A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- hydrogen
- phosphoric acid
- amides
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000001408 amides Chemical class 0.000 title claims description 8
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000007935 neutral effect Effects 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BMIMNRPAEPIYDN-UHFFFAOYSA-N 3-methyl-2-quinoxalinol Chemical compound C1=CC=C2N=C(O)C(C)=NC2=C1 BMIMNRPAEPIYDN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YXHOLYSXLHTIOT-UHFFFAOYSA-N 6,7-dimethyl-1h-quinoxalin-2-one Chemical compound N1=CC(=O)NC2=C1C=C(C)C(C)=C2 YXHOLYSXLHTIOT-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000254001 Carausius Species 0.000 description 2
- 241000254000 Carausius morosus Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- MIIFHRBUBUHJMC-UHFFFAOYSA-N ethyl 3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1=CC=C2NC(=O)C(C(=O)OCC)=NC2=C1 MIIFHRBUBUHJMC-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- -1 isooctylphenyl Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- FKHNZQFCDGOQGV-UHFFFAOYSA-N 2,3-dimethylquinoxaline Chemical compound C1=CC=C2N=C(C)C(C)=NC2=C1 FKHNZQFCDGOQGV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 235000015001 Cucumis melo var inodorus Nutrition 0.000 description 1
- 240000002495 Cucumis melo var. inodorus Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001049902 Kuehniella Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- HTHKZOCCOVYKKI-UHFFFAOYSA-N dinaphthalen-1-ylmethanedisulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)O)S(O)(=O)=O)=CC=CC2=C1 HTHKZOCCOVYKKI-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- 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
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH413469A CH485773A (de) | 1965-09-03 | 1965-09-03 | Verfahren zur Herstellung neuer (Thio-)Phosphorsäureester bzw. -amide |
| NL6611511A NL6611511A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-09-03 | 1966-08-16 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1233765A CH478843A (de) | 1965-09-03 | 1965-09-03 | Verfahren zur Herstellung neuer (Thio-) Phosphorsäureester |
| CH413469A CH485773A (de) | 1965-09-03 | 1965-09-03 | Verfahren zur Herstellung neuer (Thio-)Phosphorsäureester bzw. -amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH485773A true CH485773A (de) | 1970-02-15 |
Family
ID=25694773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH413469A CH485773A (de) | 1965-09-03 | 1965-09-03 | Verfahren zur Herstellung neuer (Thio-)Phosphorsäureester bzw. -amide |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH485773A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| NL (1) | NL6611511A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1965
- 1965-09-03 CH CH413469A patent/CH485773A/de not_active IP Right Cessation
-
1966
- 1966-08-16 NL NL6611511A patent/NL6611511A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6611511A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |