DE2325043A1 - Organophosphorderivate von isothiazol und verfahren zur herstellung - Google Patents
Organophosphorderivate von isothiazol und verfahren zur herstellungInfo
- Publication number
- DE2325043A1 DE2325043A1 DE19732325043 DE2325043A DE2325043A1 DE 2325043 A1 DE2325043 A1 DE 2325043A1 DE 19732325043 DE19732325043 DE 19732325043 DE 2325043 A DE2325043 A DE 2325043A DE 2325043 A1 DE2325043 A1 DE 2325043A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- radical
- cyano
- hydrogen atom
- thiophosphoryloxy
- 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
- 150000003854 isothiazoles Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- -1 aralkyl radical Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- VZTTYAJKYYAEGT-UHFFFAOYSA-N 5-phenyl-1,2-thiazole-4-carbonitrile Chemical compound C1=NSC(C=2C=CC=CC=2)=C1C#N VZTTYAJKYYAEGT-UHFFFAOYSA-N 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- UXSDTHOKNGARFT-UHFFFAOYSA-N 5-methyl-1,2-thiazole-4-carbonitrile Chemical compound CC=1SN=CC=1C#N UXSDTHOKNGARFT-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003580 thiophosphoric acid esters Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims 1
- ITUJMKDRDUYEBE-UHFFFAOYSA-N 5-butyl-3-dimethoxyphosphinothioyloxy-1,2-thiazole-4-carbonitrile Chemical compound CCCCC=1SN=C(OP(=S)(OC)OC)C=1C#N ITUJMKDRDUYEBE-UHFFFAOYSA-N 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 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
- 239000000047 product Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000011149 active material Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000005949 Malathion Substances 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229960000453 malathion Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WWXIKWUJNXJUOH-UHFFFAOYSA-N 3-butyl-1,2-thiazole Chemical compound C(CCC)C1=NSC=C1 WWXIKWUJNXJUOH-UHFFFAOYSA-N 0.000 description 2
- OPRDRQRQIPAQCW-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-5-methyl-1,2-thiazole-4-carboxamide Chemical compound CCOP(=S)(OCC)OC1=NSC(C)=C1C(N)=O OPRDRQRQIPAQCW-UHFFFAOYSA-N 0.000 description 2
- HYZMEPGDUROWOJ-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-5-phenyl-1,2-thiazole-4-carbonitrile Chemical compound CCOP(=S)(OCC)OC1=NSC(C=2C=CC=CC=2)=C1C#N HYZMEPGDUROWOJ-UHFFFAOYSA-N 0.000 description 2
- VQCCQZJXURHGBS-UHFFFAOYSA-N 3-oxo-5-phenyl-1,2-thiazole-4-carbonitrile Chemical compound OC1=NSC(C=2C=CC=CC=2)=C1C#N VQCCQZJXURHGBS-UHFFFAOYSA-N 0.000 description 2
- LBBKWEDRPDGXPM-UHFFFAOYSA-N 5-methyl-1,2-thiazole Chemical compound CC1=CC=NS1 LBBKWEDRPDGXPM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- HAZKAOWMLDPHGV-UHFFFAOYSA-N 2-(1-sulfanylpentylidene)propanedinitrile Chemical compound CCCCC(S)=C(C#N)C#N HAZKAOWMLDPHGV-UHFFFAOYSA-N 0.000 description 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RPYJVKZMVBBKKW-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-5-methyl-1,2-thiazole-4-carbonitrile Chemical compound CCOP(=S)(OCC)OC1=NSC(C)=C1C#N RPYJVKZMVBBKKW-UHFFFAOYSA-N 0.000 description 1
- ROIWWXOUFIPJFC-UHFFFAOYSA-N 3-dimethoxyphosphinothioyloxy-5-phenyl-1,2-thiazole-4-carbonitrile Chemical compound COP(=S)(OC)OC1=NSC(C=2C=CC=CC=2)=C1C#N ROIWWXOUFIPJFC-UHFFFAOYSA-N 0.000 description 1
- WOTIUKDGJBXFLG-UHFFFAOYSA-N 3-methyl-1,2-thiazole Chemical compound CC=1C=CSN=1 WOTIUKDGJBXFLG-UHFFFAOYSA-N 0.000 description 1
- CGNYVWLEPZQHJM-UHFFFAOYSA-N 5-butyl-1,2-thiazole Chemical compound CCCCC1=CC=NS1 CGNYVWLEPZQHJM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KLXFSKITMRWDPM-UHFFFAOYSA-N diethyl 2-sulfanylbutanedioate Chemical compound CCOC(=O)CC(S)C(=O)OCC KLXFSKITMRWDPM-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- UPMYUYREEGUGIX-UHFFFAOYSA-N ethyl pentanedithioate Chemical compound CCCCC(=S)SCC UPMYUYREEGUGIX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GRKWHXNAHIMNJD-UHFFFAOYSA-N methoxysulfanyloxymethane Chemical compound COSOC GRKWHXNAHIMNJD-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7217578A FR2184438B1 (enrdf_load_stackoverflow) | 1972-05-17 | 1972-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2325043A1 true DE2325043A1 (de) | 1973-12-06 |
Family
ID=9098637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732325043 Pending DE2325043A1 (de) | 1972-05-17 | 1973-05-17 | Organophosphorderivate von isothiazol und verfahren zur herstellung |
Country Status (17)
-
1972
- 1972-05-17 FR FR7217578A patent/FR2184438B1/fr not_active Expired
-
1973
- 1973-04-27 OA OA54890A patent/OA04374A/xx unknown
- 1973-05-01 IL IL42161A patent/IL42161A/en unknown
- 1973-05-04 CH CH637873A patent/CH571820A5/xx not_active IP Right Cessation
- 1973-05-15 BR BR353873A patent/BR7303538D0/pt unknown
- 1973-05-15 BG BG023612A patent/BG26799A3/xx unknown
- 1973-05-15 DD DD17084973A patent/DD108195A5/xx unknown
- 1973-05-16 SU SU1913402A patent/SU489336A3/ru active
- 1973-05-16 BE BE131183A patent/BE799614A/xx unknown
- 1973-05-16 NL NL7306802A patent/NL7306802A/xx not_active Application Discontinuation
- 1973-05-16 EG EG18373A patent/EG10879A/xx active
- 1973-05-16 ES ES414789A patent/ES414789A1/es not_active Expired
- 1973-05-17 IT IT5005373A patent/IT986086B/it active
- 1973-05-17 GB GB2351073A patent/GB1397882A/en not_active Expired
- 1973-05-17 JP JP5421373A patent/JPS4941371A/ja active Pending
- 1973-05-17 HU HURO000729 patent/HU168973B/hu unknown
- 1973-05-17 DE DE19732325043 patent/DE2325043A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE799614A (fr) | 1973-11-16 |
| IL42161A0 (en) | 1973-07-30 |
| HU168973B (enrdf_load_stackoverflow) | 1976-08-28 |
| EG10879A (en) | 1976-10-31 |
| JPS4941371A (enrdf_load_stackoverflow) | 1974-04-18 |
| SU489336A3 (ru) | 1975-10-25 |
| FR2184438B1 (enrdf_load_stackoverflow) | 1974-07-26 |
| IT986086B (it) | 1975-01-10 |
| CH571820A5 (enrdf_load_stackoverflow) | 1976-01-30 |
| BR7303538D0 (pt) | 1974-08-15 |
| ES414789A1 (es) | 1976-01-16 |
| OA04374A (fr) | 1980-02-15 |
| BG26799A3 (bg) | 1979-06-12 |
| FR2184438A1 (enrdf_load_stackoverflow) | 1973-12-28 |
| IL42161A (en) | 1976-06-30 |
| NL7306802A (enrdf_load_stackoverflow) | 1973-11-20 |
| GB1397882A (en) | 1975-06-18 |
| DD108195A5 (enrdf_load_stackoverflow) | 1974-09-12 |
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