DE2301704A1 - 3-(1,3,4-thiadiazol-2-yl)-5-hydroxyhydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide - Google Patents
3-(1,3,4-thiadiazol-2-yl)-5-hydroxyhydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizideInfo
- Publication number
- DE2301704A1 DE2301704A1 DE2301704A DE2301704A DE2301704A1 DE 2301704 A1 DE2301704 A1 DE 2301704A1 DE 2301704 A DE2301704 A DE 2301704A DE 2301704 A DE2301704 A DE 2301704A DE 2301704 A1 DE2301704 A1 DE 2301704A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazol
- methyl
- hydroxy
- parabanic acid
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000004009 herbicide Substances 0.000 title claims description 7
- QMRZFXRZMZMVSP-UHFFFAOYSA-N 5-hydroxy-3-(1,3,4-thiadiazol-2-yl)imidazolidine-2,4-dione Chemical compound O=C1C(O)NC(=O)N1C1=NN=CS1 QMRZFXRZMZMVSP-UHFFFAOYSA-N 0.000 title claims 2
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- -1 5-tert-butyl-1,3,4-thiadiazol-2-yl Chemical group 0.000 description 36
- 239000004480 active ingredient Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 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
- 239000000969 carrier Substances 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HRUQFAAWUDHYBX-UHFFFAOYSA-N 5-hydroxy-3-methyl-1-phenylimidazolidine-2,4-dione Chemical compound O=C1N(C)C(=O)C(O)N1C1=CC=CC=C1 HRUQFAAWUDHYBX-UHFFFAOYSA-N 0.000 description 2
- 241001049165 Caria Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 235000017945 Matricaria Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 240000006694 Stellaria media Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
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- 231100000001 growth retardation Toxicity 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BRHPZMIMYFCAMS-UHFFFAOYSA-N 1-(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)-3-methylurea Chemical compound CCSC1=NN=C(NC(=O)NC)S1 BRHPZMIMYFCAMS-UHFFFAOYSA-N 0.000 description 1
- QNZVDHFCJIENKD-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-methylurea Chemical compound CNC(=O)NC1=NN=C(C(C)(C)C)S1 QNZVDHFCJIENKD-UHFFFAOYSA-N 0.000 description 1
- FTYDUPPPGMRNGZ-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)C(O)C(=O)N1C1=NN=C(C(C)(C)C)S1 FTYDUPPPGMRNGZ-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
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- 240000003705 Senecio vulgaris Species 0.000 description 1
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA740207A ZA74207B (en) | 1973-01-13 | 1973-01-11 | "3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoins,process for their preparation and their use as herbicides |
| DE2301704A DE2301704A1 (de) | 1973-01-13 | 1973-01-13 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxyhydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| EG486/73A EG11177A (en) | 1973-01-13 | 1973-12-27 | 3-(1,3,4-thiadiazol-2-yl-)-5-hydroxy-hydantoins,process for their preparation and their use as herbicides |
| SU1980519A SU555826A3 (ru) | 1973-01-13 | 1973-12-28 | Способ борьбы с нежелательной растительностью |
| BR106/74A BR7400106D0 (pt) | 1973-01-13 | 1974-01-09 | Processo para a preparacao de 3-(1,3,4-tiadiazol-2-il)5 hidestas droxi-hidantoinas, bem como composicoes herbicidas a base |
| AU64350/74A AU473738B2 (en) | 1973-01-13 | 1974-01-09 | 3-(1, 3, 4-THIADIAZOL-2-yl)-5-HYDROXYHYDANTOINS PROCESS FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES |
| RO7400077228A RO63661A (fr) | 1973-01-13 | 1974-01-09 | Procede pour la preparation des derives du 3-(1,2,4-thiadiazol-2-ile)-5-hydroxy-hydantoine |
| TR17381A TR17381A (tr) | 1973-01-13 | 1974-01-10 | 3-(1-3,4-tiadiazol-2-il)-5-hidroksi-hidantoinler,bunlarin hazirlanmasina mahsus usuller,ve bunlarin herbisid olarak kullanilmalari |
| IL43985A IL43985A (en) | 1973-01-13 | 1974-01-10 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoins,their preparation and herbicidal compositions containing them |
| LU69140A LU69140A1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-10 | |
| NL7400355A NL7400355A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-10 | |
| DK15474A DK136068C (da) | 1973-01-13 | 1974-01-11 | Herbicidt virksomme 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoiner |
| AT23474*#A AT328218B (de) | 1973-01-13 | 1974-01-11 | Herbizides mittel |
| DD175961A DD110742A5 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| CA189,989A CA1029731A (en) | 1973-01-13 | 1974-01-11 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoin compounds and herbicidal compositions |
| HUBA3014A HU168897B (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| CH39374A CH584709A5 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| BE139718A BE809638A (fr) | 1973-01-13 | 1974-01-11 | Nouvelles 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoines, leur procede de preparation et leur application |
| GB137374A GB1445912A (en) | 1973-01-13 | 1974-01-11 | 3-1,3,4-thiadiazol-2-yl-5-hydroxy-hydantoins process for their preparatiion and their use as herbicides |
| IE64/74A IE38734B1 (en) | 1973-01-13 | 1974-01-11 | 3-(1,3.4-thiadiazol-2-yl)-5-hydroxyhydantoins, process fortheir preparation and their use as herbicides |
| FR7400966A FR2213942B1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| PL1974168055A PL88499B1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| JP49006358A JPS49108077A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-12 | |
| ES422258A ES422258A1 (es) | 1973-01-13 | 1974-01-12 | Procedimiento para preparar 3-(1, 3, 4-tiadiazol-2-il)-5- hidroxi-hidantoinas. |
| JP49006359A JPS49108243A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2301704A DE2301704A1 (de) | 1973-01-13 | 1973-01-13 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxyhydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2301704A1 true DE2301704A1 (de) | 1974-07-18 |
Family
ID=5868976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2301704A Pending DE2301704A1 (de) | 1973-01-13 | 1973-01-13 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxyhydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Country Status (24)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2013418A1 (de) * | 1970-03-20 | 1971-10-07 | I (1,3,4 Thiadiazol 2 yl) lmidazohdi non (2) Derivate, Verfahren zu ihrer Her stellung und ihre Verwendung als herbizide | |
| BE789441A (fr) * | 1971-09-30 | 1973-03-29 | Ciba Geigy | Nouvel herbicide selectif et procede pour sa preparation |
-
1973
- 1973-01-11 ZA ZA740207A patent/ZA74207B/xx unknown
- 1973-01-13 DE DE2301704A patent/DE2301704A1/de active Pending
- 1973-12-27 EG EG486/73A patent/EG11177A/xx active
- 1973-12-28 SU SU1980519A patent/SU555826A3/ru active
-
1974
- 1974-01-09 BR BR106/74A patent/BR7400106D0/pt unknown
- 1974-01-09 AU AU64350/74A patent/AU473738B2/en not_active Expired
- 1974-01-09 RO RO7400077228A patent/RO63661A/ro unknown
- 1974-01-10 IL IL43985A patent/IL43985A/en unknown
- 1974-01-10 LU LU69140A patent/LU69140A1/xx unknown
- 1974-01-10 TR TR17381A patent/TR17381A/xx unknown
- 1974-01-10 NL NL7400355A patent/NL7400355A/xx not_active Application Discontinuation
- 1974-01-11 HU HUBA3014A patent/HU168897B/hu unknown
- 1974-01-11 DK DK15474A patent/DK136068C/da active
- 1974-01-11 CH CH39374A patent/CH584709A5/xx not_active IP Right Cessation
- 1974-01-11 PL PL1974168055A patent/PL88499B1/pl unknown
- 1974-01-11 BE BE139718A patent/BE809638A/xx unknown
- 1974-01-11 AT AT23474*#A patent/AT328218B/de not_active IP Right Cessation
- 1974-01-11 DD DD175961A patent/DD110742A5/xx unknown
- 1974-01-11 FR FR7400966A patent/FR2213942B1/fr not_active Expired
- 1974-01-11 IE IE64/74A patent/IE38734B1/xx unknown
- 1974-01-11 GB GB137374A patent/GB1445912A/en not_active Expired
- 1974-01-11 CA CA189,989A patent/CA1029731A/en not_active Expired
- 1974-01-12 JP JP49006358A patent/JPS49108077A/ja active Pending
- 1974-01-12 JP JP49006359A patent/JPS49108243A/ja active Pending
- 1974-01-12 ES ES422258A patent/ES422258A1/es not_active Expired
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