IL45905A - Thiazole derivatives process for preparing them and insecticidal acaricidal and nematicidal compositions - Google Patents
Thiazole derivatives process for preparing them and insecticidal acaricidal and nematicidal compositionsInfo
- Publication number
- IL45905A IL45905A IL45905A IL4590574A IL45905A IL 45905 A IL45905 A IL 45905A IL 45905 A IL45905 A IL 45905A IL 4590574 A IL4590574 A IL 4590574A IL 45905 A IL45905 A IL 45905A
- Authority
- IL
- Israel
- Prior art keywords
- thiazole
- carbon atoms
- diethoxythiophosphoryloxy
- radical
- alkyl radical
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 21
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 11
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000007979 thiazole derivatives Chemical class 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 23
- 239000011149 active material Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- IEXVIGWLRZMOMB-UHFFFAOYSA-N diethoxy-sulfanylidene-(1,3-thiazol-2-yloxy)-lambda5-phosphane Chemical compound C(C)OP(=S)(OCC)OC=1SC=CN1 IEXVIGWLRZMOMB-UHFFFAOYSA-N 0.000 claims 3
- QMHIMXFNBOYPND-UHFFFAOYSA-N 4-methylthiazole Chemical compound CC1=CSC=N1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- BSZAGUQSRQYDFH-UHFFFAOYSA-N 1-(2-diethoxyphosphinothioyloxy-1,3-thiazol-4-yl)ethanone Chemical compound CCOP(=S)(OCC)OC1=NC(C(C)=O)=CS1 BSZAGUQSRQYDFH-UHFFFAOYSA-N 0.000 claims 1
- DKFSWYMAIUBORX-UHFFFAOYSA-N 2-diethoxyphosphinothioyloxy-4-methyl-1,3-thiazole-5-carbonitrile Chemical compound CCOP(=S)(OCC)OC1=NC(C)=C(C#N)S1 DKFSWYMAIUBORX-UHFFFAOYSA-N 0.000 claims 1
- LTICUSGQLHOWQO-UHFFFAOYSA-N 5-hexyl-1,3-thiazole Chemical compound CCCCCCC1=CN=CS1 LTICUSGQLHOWQO-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- UQQFYIPKUWAHBN-UHFFFAOYSA-N diethoxy-[(4-methyl-1,3-thiazol-2-yl)oxy]-sulfanylidene-lambda5-phosphane Chemical compound CC=1N=C(SC=1)OP(=S)(OCC)OCC UQQFYIPKUWAHBN-UHFFFAOYSA-N 0.000 claims 1
- PXEMLJMWQMHBNV-UHFFFAOYSA-N ethyl 2-(2-diethoxyphosphinothioyloxy-1,3-thiazol-4-yl)acetate Chemical compound CCOC(=O)CC1=CSC(OP(=S)(OCC)OCC)=N1 PXEMLJMWQMHBNV-UHFFFAOYSA-N 0.000 claims 1
- MMQDFHBAIMAXMM-UHFFFAOYSA-N ethyl 2-(2-diethoxyphosphinothioyloxy-4-methyl-1,3-thiazol-5-yl)acetate Chemical compound CCOC(=O)CC=1SC(OP(=S)(OCC)OCC)=NC=1C MMQDFHBAIMAXMM-UHFFFAOYSA-N 0.000 claims 1
- NYCAYUNOMWVPOZ-UHFFFAOYSA-N ethyl 5-bromo-2-diethoxyphosphinothioyloxy-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=C(OP(=S)(OCC)OCC)SC=1Br NYCAYUNOMWVPOZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 15
- -1 THIAZOLE PHOSPHORYL Chemical class 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- 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 9
- 238000002360 preparation method Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000000038 chest Anatomy 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZBAJBHOFDSMEQT-UHFFFAOYSA-N 1,3-thiazole Chemical compound C1=CSC=N1.C1=CSC=N1 ZBAJBHOFDSMEQT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000255579 Ceratitis capitata 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
- 241000254181 Sitophilus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000194 ovacidal Toxicity 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241000426499 Chilo Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 241000739471 Ditylenchus myceliophagus Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- WXJXBKBJAKPJRN-UHFFFAOYSA-N Methanephosphonothioic acid Chemical compound CP(O)(O)=S WXJXBKBJAKPJRN-UHFFFAOYSA-N 0.000 description 1
- 241000244205 Panagrellus Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002506 adulticidal effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- MYXNWWDJRWCURH-UHFFFAOYSA-N ethoxymethanethioic s-acid Chemical compound CCOC(S)=O MYXNWWDJRWCURH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C07F9/6536—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7338071A FR2249091B1 (fr) | 1973-10-25 | 1973-10-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45905A0 IL45905A0 (en) | 1974-12-31 |
| IL45905A true IL45905A (en) | 1977-05-31 |
Family
ID=9126916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45905A IL45905A (en) | 1973-10-25 | 1974-10-22 | Thiazole derivatives process for preparing them and insecticidal acaricidal and nematicidal compositions |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3948925A (fr) |
| JP (1) | JPS5070364A (fr) |
| AR (1) | AR217033A1 (fr) |
| BE (1) | BE821418A (fr) |
| BR (1) | BR7408896D0 (fr) |
| CA (1) | CA1046517A (fr) |
| CH (1) | CH606065A5 (fr) |
| DD (1) | DD117801A5 (fr) |
| DE (1) | DE2450814A1 (fr) |
| DK (1) | DK559574A (fr) |
| FR (1) | FR2249091B1 (fr) |
| GB (1) | GB1435476A (fr) |
| HU (1) | HU171035B (fr) |
| IE (1) | IE40534B1 (fr) |
| IL (1) | IL45905A (fr) |
| IT (1) | IT1050255B (fr) |
| LU (1) | LU71170A1 (fr) |
| NL (1) | NL7413911A (fr) |
| PH (1) | PH11405A (fr) |
| SU (1) | SU598540A3 (fr) |
| TR (1) | TR18578A (fr) |
| ZA (1) | ZA746695B (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203899A (en) * | 1974-12-19 | 1980-05-20 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| US4188299A (en) * | 1978-05-17 | 1980-02-12 | Standard Oil Company (Indiana) | Oil soluble dithiophosphoric acid derivatives of mercaptothiadiazoles |
| US4649146A (en) * | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
| GB8302591D0 (en) * | 1983-01-31 | 1983-03-02 | Fujisawa Pharmaceutical Co | Thiazole derivatives |
| US4762849A (en) * | 1985-10-15 | 1988-08-09 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic alkanoylthiazolones |
| CA1291950C (fr) * | 1985-10-15 | 1991-11-12 | J. Martin Grisar | Aroylthiazolones cardiotoniques |
| US4927939A (en) * | 1985-10-15 | 1990-05-22 | Merrell Dow Pharmaceuticals | Cardiotonic aroylthiazolones |
| CA1266268C (fr) * | 1985-10-15 | 1990-02-27 | Aroylthiazolones cardiotoniques |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159645A (en) * | 1960-12-29 | 1964-12-01 | Dow Chemical Co | Omcrion-thiazolyl omcrion-alkyl phosphoramido-thioates |
| BE755027A (fr) * | 1969-08-19 | 1971-02-19 | Bayer Ag | Esters d'acides thiazolo-(thiono)-phosphoriques et- phosphoriques, leurprocede de preparation et leur application comme insecticides et acaricides |
| DE2064307A1 (de) * | 1970-12-29 | 1972-07-06 | Bayer Ag | Thiazolo-(thiono)-phosphor-(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide |
| GB1323263A (en) * | 1971-03-12 | 1973-07-11 | Shell Int Research | Phosphorus-containing thiazole derivatives having pesticidal properties |
-
1973
- 1973-10-25 FR FR7338071A patent/FR2249091B1/fr not_active Expired
-
1974
- 1974-10-17 US US05/515,479 patent/US3948925A/en not_active Expired - Lifetime
- 1974-10-21 DD DD181809A patent/DD117801A5/xx unknown
- 1974-10-22 ZA ZA00746695A patent/ZA746695B/xx unknown
- 1974-10-22 IL IL45905A patent/IL45905A/en unknown
- 1974-10-24 CH CH1426074A patent/CH606065A5/xx not_active IP Right Cessation
- 1974-10-24 BE BE149828A patent/BE821418A/fr unknown
- 1974-10-24 BR BR8896/74A patent/BR7408896D0/pt unknown
- 1974-10-24 PH PH16446A patent/PH11405A/en unknown
- 1974-10-24 LU LU71170A patent/LU71170A1/xx unknown
- 1974-10-24 NL NL7413911A patent/NL7413911A/xx not_active Application Discontinuation
- 1974-10-24 GB GB4685574A patent/GB1435476A/en not_active Expired
- 1974-10-24 HU HU74RO00000806A patent/HU171035B/hu unknown
- 1974-10-24 CA CA212,199A patent/CA1046517A/fr not_active Expired
- 1974-10-24 JP JP49122003A patent/JPS5070364A/ja active Pending
- 1974-10-24 IT IT53716/74A patent/IT1050255B/it active
- 1974-10-24 AR AR256237A patent/AR217033A1/es active
- 1974-10-25 DE DE19742450814 patent/DE2450814A1/de not_active Withdrawn
- 1974-10-25 TR TR18578A patent/TR18578A/xx unknown
- 1974-10-25 DK DK559574A patent/DK559574A/da unknown
- 1974-10-25 IE IE2203/74A patent/IE40534B1/xx unknown
-
1975
- 1975-08-07 SU SU752162200A patent/SU598540A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7408896D0 (pt) | 1975-09-02 |
| PH11405A (en) | 1977-12-14 |
| CA1046517A (fr) | 1979-01-16 |
| HU171035B (hu) | 1977-10-28 |
| TR18578A (tr) | 1977-04-13 |
| US3948925A (en) | 1976-04-06 |
| JPS5070364A (fr) | 1975-06-11 |
| IL45905A0 (en) | 1974-12-31 |
| BE821418A (fr) | 1975-04-24 |
| IE40534B1 (en) | 1979-06-20 |
| LU71170A1 (fr) | 1975-06-24 |
| DK559574A (fr) | 1975-06-16 |
| DE2450814A1 (de) | 1975-04-30 |
| CH606065A5 (fr) | 1978-10-13 |
| SU598540A3 (ru) | 1978-03-15 |
| ZA746695B (en) | 1975-11-26 |
| AR217033A1 (es) | 1980-02-29 |
| DD117801A5 (fr) | 1976-02-05 |
| NL7413911A (nl) | 1975-04-29 |
| FR2249091A1 (fr) | 1975-05-23 |
| IE40534L (en) | 1975-04-25 |
| GB1435476A (en) | 1976-05-12 |
| IT1050255B (it) | 1981-03-10 |
| FR2249091B1 (fr) | 1978-11-17 |
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