DE1445029B1 - Thiol- bzw. Thionothiolphosphorsaeureester - Google Patents
Thiol- bzw. ThionothiolphosphorsaeureesterInfo
- Publication number
- DE1445029B1 DE1445029B1 DE19601445029D DE1445029DA DE1445029B1 DE 1445029 B1 DE1445029 B1 DE 1445029B1 DE 19601445029 D DE19601445029 D DE 19601445029D DE 1445029D A DE1445029D A DE 1445029DA DE 1445029 B1 DE1445029 B1 DE 1445029B1
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- compounds
- thiol
- och
- general formula
- 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
- 239000002253 acid Substances 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 5
- 150000003573 thiols Chemical class 0.000 title claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000002917 insecticide Substances 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- FOHRCMUANUUOIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-benzoxazol-2-one Chemical class C1=CC=C2OC(=O)N(CO)C2=C1 FOHRCMUANUUOIL-UHFFFAOYSA-N 0.000 claims 1
- 241001124076 Aphididae Species 0.000 claims 1
- 241000256113 Culicidae Species 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 241000254179 Sitophilus granarius Species 0.000 claims 1
- 241001454295 Tetranychidae Species 0.000 claims 1
- 230000000895 acaricidal effect Effects 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RCIAHUSTMGHSEB-UHFFFAOYSA-N 3-(bromomethyl)-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(=S)N(CBr)C2=C1 RCIAHUSTMGHSEB-UHFFFAOYSA-N 0.000 description 2
- XHZRTBILUWRQBR-UHFFFAOYSA-N 3-(chloromethyl)-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(=S)N(CCl)C2=C1 XHZRTBILUWRQBR-UHFFFAOYSA-N 0.000 description 2
- GRDSKYXJFDDYFD-UHFFFAOYSA-N 3-(chloromethyl)-1,3-benzoxazole-2-thione Chemical compound C1=CC=C2OC(=S)N(CCl)C2=C1 GRDSKYXJFDDYFD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- -1 N-chloromethyl benzoxazole Chemical compound 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- ATBPGPNOOVIFLN-UHFFFAOYSA-N azanium;methoxy-methylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [NH4+].COP([O-])(=S)SC ATBPGPNOOVIFLN-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010626 work up procedure 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65324—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0032171 | 1960-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445029B1 true DE1445029B1 (de) | 1972-02-03 |
Family
ID=7094524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19601445029D Pending DE1445029B1 (de) | 1960-09-22 | 1960-09-22 | Thiol- bzw. Thionothiolphosphorsaeureester |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE608380A (enrdf_load_stackoverflow) |
| BR (1) | BR6132858D0 (enrdf_load_stackoverflow) |
| DE (1) | DE1445029B1 (enrdf_load_stackoverflow) |
| NL (1) | NL269468A (enrdf_load_stackoverflow) |
-
0
- BE BE608380D patent/BE608380A/fr unknown
-
1960
- 1960-09-22 DE DE19601445029D patent/DE1445029B1/de active Pending
-
1961
- 1961-09-21 NL NL269468D patent/NL269468A/xx unknown
- 1961-09-22 BR BR132858/61A patent/BR6132858D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6132858D0 (pt) | 1973-08-16 |
| BE608380A (enrdf_load_stackoverflow) | |
| NL269468A (enrdf_load_stackoverflow) |
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