CH644385A5 - Organophosphorsaeure- und organothionophosphorsaeurederivate. - Google Patents
Organophosphorsaeure- und organothionophosphorsaeurederivate. Download PDFInfo
- Publication number
- CH644385A5 CH644385A5 CH87880A CH87880A CH644385A5 CH 644385 A5 CH644385 A5 CH 644385A5 CH 87880 A CH87880 A CH 87880A CH 87880 A CH87880 A CH 87880A CH 644385 A5 CH644385 A5 CH 644385A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ch2och3
- och
- general formula
- methyl
- ch2sch3
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 59
- 238000002360 preparation method Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- -1 methylmercapto group Chemical group 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 230000000895 acaricidal effect Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000005645 nematicide Substances 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- 230000001069 nematicidal effect Effects 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 150000008081 1H-pyrimidin-4-ones Chemical class 0.000 claims description 6
- 241000238876 Acari Species 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 6
- 241000244206 Nematoda Species 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 6
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 5
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 claims 4
- 150000002366 halogen compounds Chemical class 0.000 claims 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000003230 pyrimidines Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 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 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 claims 1
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 claims 1
- FOTXPHXUXCRDPB-UHFFFAOYSA-N 2,4-bis(methoxymethyl)pyrimidine Chemical compound COCC1=CC=NC(COC)=N1 FOTXPHXUXCRDPB-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 claims 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- MCKANBCWFDYIJO-UHFFFAOYSA-N chloro-dihydroxy-imino-$l^{5}-phosphane Chemical class NP(O)(Cl)=O MCKANBCWFDYIJO-UHFFFAOYSA-N 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
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- 238000004821 distillation Methods 0.000 claims 1
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- 150000002576 ketones Chemical class 0.000 claims 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims 1
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- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
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- 238000011534 incubation Methods 0.000 description 1
- 239000000201 insect hormone Substances 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000003949 liquefied natural gas Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000005642 phosphothioate group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
-
- 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
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen 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
- C07F9/645—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
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1249779A JPS55104295A (en) | 1979-02-05 | 1979-02-05 | Pyrimidin-4-yl(thio)phosphoric acid ester, its preparation, and insecticide, miticide, and nematocide containing the compound as effective component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH644385A5 true CH644385A5 (de) | 1984-07-31 |
Family
ID=11807001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH87880A CH644385A5 (de) | 1979-02-05 | 1980-02-04 | Organophosphorsaeure- und organothionophosphorsaeurederivate. |
Country Status (9)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382087A (en) * | 1981-05-04 | 1983-05-03 | Olin Corporation | Selected O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphorothionates and O-(2-trichloromethyl-4-pyrimidinyl)-O,O-dialkyl phosphoronates and their use as insecticides |
| US4395551A (en) * | 1981-12-10 | 1983-07-26 | Uniroyal, Inc. | Pyridopyrimidinone compounds |
| US4472389A (en) * | 1981-12-10 | 1984-09-18 | Uniroyal, Inc. | Substituted pyrimidinyl organophosphorus insecticides |
| US4634690A (en) * | 1981-12-10 | 1987-01-06 | Uniroyal Chemical Company, Inc. | Substituted pyrimidinyl organophosphorus insecticides |
| US4496728A (en) * | 1982-09-20 | 1985-01-29 | Ciba-Geigy Corporation | Method for the production of 2-isopropyl-4-methyl-6-hydroxypyrimidine |
| US4489068A (en) * | 1983-04-28 | 1984-12-18 | The Dow Chemical Company | Method and composition for enhancing the insecticidal activity of certain organophosphorus compounds |
| DE3420166A1 (de) * | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Pyrimidylphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| US5034529A (en) * | 1988-04-28 | 1991-07-23 | Ciba-Geigy Corporation | Process for the production of thiophosphoric acid esters of hydroxypyrimidines |
| US5466458A (en) * | 1992-03-09 | 1995-11-14 | Roussel Uclaf | Emulsified spray formulations |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE641253A (US20020128544A1-20020912-P00008.png) * | ||||
| NL86689C (US20020128544A1-20020912-P00008.png) * | 1951-04-20 | 1900-01-01 | ||
| US3159630A (en) * | 1961-06-14 | 1964-12-01 | Dow Chemical Co | Pyrimidinyl omicron-alkyl phosphoramidates and phosphoramidothioates |
| FR1369062A (fr) * | 1962-08-24 | 1964-08-07 | Bayer Ag | Nouvelles compositions insecticides et acaricides et leur procédé de fabrication |
| NL296930A (US20020128544A1-20020912-P00008.png) * | 1962-08-24 | 1900-01-01 | ||
| GB1436754A (en) | 1973-05-16 | 1976-05-26 | Sandoz Ltd | Phosphoric and thionophosphoric acid esters and esteramides |
| JPS547109B2 (US20020128544A1-20020912-P00008.png) * | 1973-06-25 | 1979-04-04 | ||
| DE2703310A1 (de) * | 1977-01-27 | 1978-08-03 | Bayer Ag | Substituierte pyrimidinyl(thio)- phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| DE2747357A1 (de) | 1977-10-21 | 1979-04-26 | Bayer Ag | Substituierte pyrimidinyl(thiono) (thiol)phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2804889A1 (de) | 1978-02-04 | 1979-08-16 | Hoechst Ag | (thio)phosphor- und -phosphonsaeureester von substituierten pyrimidinen, ihre herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
-
1979
- 1979-02-05 JP JP1249779A patent/JPS55104295A/ja active Pending
-
1980
- 1980-01-24 US US06/114,737 patent/US4308258A/en not_active Expired - Lifetime
- 1980-01-30 GB GB8003113A patent/GB2043643B/en not_active Expired
- 1980-01-30 DE DE19803003337 patent/DE3003337A1/de not_active Withdrawn
- 1980-02-01 IT IT8047779A patent/IT1143914B/it active
- 1980-02-04 NL NL8000688A patent/NL8000688A/nl not_active Application Discontinuation
- 1980-02-04 FR FR8002389A patent/FR2447915A1/fr active Granted
- 1980-02-04 PH PH23585A patent/PH17500A/en unknown
- 1980-02-04 CH CH87880A patent/CH644385A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3003337A1 (de) | 1980-08-14 |
| NL8000688A (nl) | 1980-08-07 |
| FR2447915B1 (US20020128544A1-20020912-P00008.png) | 1984-01-27 |
| IT8047779A0 (it) | 1980-02-01 |
| JPS55104295A (en) | 1980-08-09 |
| GB2043643B (en) | 1983-05-11 |
| FR2447915A1 (fr) | 1980-08-29 |
| US4308258A (en) | 1981-12-29 |
| IT1143914B (it) | 1986-10-29 |
| PH17500A (en) | 1984-09-07 |
| GB2043643A (en) | 1980-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |