CA1031789A - Preparation process of new substituted crotonanilides - Google Patents
Preparation process of new substituted crotonanilidesInfo
- Publication number
- CA1031789A CA1031789A CA182,013A CA182013A CA1031789A CA 1031789 A CA1031789 A CA 1031789A CA 182013 A CA182013 A CA 182013A CA 1031789 A CA1031789 A CA 1031789A
- Authority
- CA
- Canada
- Prior art keywords
- atomes
- carbone
- radical
- méthoxy
- crotonanilide
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 29
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- BZSYYMAHNJHZCB-QHHAFSJGSA-N (e)-n-phenylbut-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=CC=C1 BZSYYMAHNJHZCB-QHHAFSJGSA-N 0.000 claims description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 150000003931 anilides Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 abstract description 8
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 235000008216 herbs Nutrition 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 241000743339 Agrostis Species 0.000 description 6
- 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 6
- 239000004148 curcumin Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241001448862 Croton Species 0.000 description 4
- 241001101998 Galium Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 3
- 241000219053 Rumex Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- FIKZNDXGHPLFEI-VURMDHGXSA-N (z)-n-(3-acetylphenyl)-3-chlorobut-2-enamide Chemical compound C\C(Cl)=C\C(=O)NC1=CC=CC(C(C)=O)=C1 FIKZNDXGHPLFEI-VURMDHGXSA-N 0.000 description 2
- CJPISHNVIOEHRY-NTMALXAHSA-N (z)-n-(3-butanoylphenyl)-3-chlorobut-2-enamide Chemical compound CCCC(=O)C1=CC=CC(NC(=O)\C=C(\C)Cl)=C1 CJPISHNVIOEHRY-NTMALXAHSA-N 0.000 description 2
- HMNZRAXGYXHWLG-UHFFFAOYSA-N 3-methoxy-n-phenylhex-2-enamide Chemical compound CCCC(OC)=CC(=O)NC1=CC=CC=C1 HMNZRAXGYXHWLG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005573 Linuron Substances 0.000 description 2
- 241001508691 Martes zibellina Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940082150 encore Drugs 0.000 description 2
- 229940028332 halog Drugs 0.000 description 2
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 2
- JBTCHCWUNMZNEO-UHFFFAOYSA-N n-phenylhexanamide Chemical compound CCCCCC(=O)NC1=CC=CC=C1 JBTCHCWUNMZNEO-UHFFFAOYSA-N 0.000 description 2
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WIBDSKKUNRWEJO-FPLPWBNLSA-N (z)-3-chloro-n-phenylbut-2-enamide Chemical compound C\C(Cl)=C\C(=O)NC1=CC=CC=C1 WIBDSKKUNRWEJO-FPLPWBNLSA-N 0.000 description 1
- JQHVNKSERJZHCO-UHFFFAOYSA-N 1-(3-aminophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=CC(N)=C1 JQHVNKSERJZHCO-UHFFFAOYSA-N 0.000 description 1
- NJVMKJXFXIAJHE-UHFFFAOYSA-N 16-(4-aminobutyl)-22-benzyl-n-(1,3-dihydroxy-2-methylpropan-2-yl)-13-(1-hydroxyethyl)-19-(1h-indol-3-ylmethyl)-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pentazaspiro[5.19]pentacosane-10-carboxamide Chemical compound N1C(=O)CC2(CCCCC2)SSCC(C(=O)NC(C)(CO)CO)NC(=O)C(C(O)C)NC(=O)C(CCCCN)NC(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1CC1=CC=CC=C1 NJVMKJXFXIAJHE-UHFFFAOYSA-N 0.000 description 1
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- WMIQWIJPGVVMII-UHFFFAOYSA-N 3-butylaniline Chemical compound CCCCC1=CC=CC(N)=C1 WMIQWIJPGVVMII-UHFFFAOYSA-N 0.000 description 1
- KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
- QKGYZEODEUWWRN-UHFFFAOYSA-N 4-imino-1-phenylpentan-2-one Chemical compound CC(=N)CC(=O)CC1=CC=CC=C1 QKGYZEODEUWWRN-UHFFFAOYSA-N 0.000 description 1
- 108700039253 ASS 51 Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QYLJIYOGHRGUIH-CIUDSAMLSA-N Arg-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N QYLJIYOGHRGUIH-CIUDSAMLSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000728904 Iais Species 0.000 description 1
- PMGCQNGBLMMXEW-UHFFFAOYSA-N Isoamyl salicylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1O PMGCQNGBLMMXEW-UHFFFAOYSA-N 0.000 description 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004429 atom Chemical group 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
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000020068 maotai Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- DDLXREKEHHNSNO-UHFFFAOYSA-N n-(3-propanethioylphenyl)acetamide Chemical compound CCC(=S)C1=CC=CC(NC(C)=O)=C1 DDLXREKEHHNSNO-UHFFFAOYSA-N 0.000 description 1
- AMLJWLYRONUCKO-UHFFFAOYSA-N n-(6-amino-5-iodopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(I)C(N)=N1 AMLJWLYRONUCKO-UHFFFAOYSA-N 0.000 description 1
- 229960005038 quinisocaine Drugs 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7233960A FR2201035B1 (enrdf_load_stackoverflow) | 1972-09-26 | 1972-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1031789A true CA1031789A (en) | 1978-05-23 |
Family
ID=9104771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA182,013A Expired CA1031789A (en) | 1972-09-26 | 1973-09-25 | Preparation process of new substituted crotonanilides |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2268010B1 (enrdf_load_stackoverflow) * | 1974-04-22 | 1976-10-29 | Roussel Uclaf | |
| GB1564387A (en) * | 1976-06-30 | 1980-04-10 | Kao Corp | Germicidal herbicide compositions for use in agriculture and horticulture containing active ingredients amides of alkylthioalkylsulphinyl and alkylsulphonyl-acrylic acids |
-
1972
- 1972-09-26 FR FR7233960A patent/FR2201035B1/fr not_active Expired
-
1973
- 1973-08-21 DD DD173003A patent/DD112712A5/xx unknown
- 1973-08-26 IL IL43076A patent/IL43076A/xx unknown
- 1973-09-04 SE SE7312036A patent/SE408413B/xx unknown
- 1973-09-19 JP JP48105100A patent/JPS5811855B2/ja not_active Expired
- 1973-09-25 CH CH1373673A patent/CH587010A5/xx not_active IP Right Cessation
- 1973-09-25 IT IT52745/73A patent/IT1047948B/it active
- 1973-09-25 BE BE136017A patent/BE805281A/xx unknown
- 1973-09-25 ES ES419038A patent/ES419038A1/es not_active Expired
- 1973-09-25 CA CA182,013A patent/CA1031789A/en not_active Expired
- 1973-09-25 SU SU731959057A patent/SU645556A3/ru active
- 1973-09-25 HU HURO752A patent/HU169385B/hu unknown
- 1973-09-26 NL NL7313245A patent/NL7313245A/xx not_active Application Discontinuation
- 1973-09-26 DE DE19732348487 patent/DE2348487A1/de not_active Withdrawn
- 1973-09-26 GB GB4511773A patent/GB1393319A/en not_active Expired
-
1975
- 1975-08-07 SU SU752162199A patent/SU626675A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BE805281A (fr) | 1974-03-25 |
| SE408413B (sv) | 1979-06-11 |
| GB1393319A (en) | 1975-05-07 |
| JPS5811855B2 (ja) | 1983-03-04 |
| DD112712A5 (de) | 1975-05-05 |
| CH587010A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| FR2201035B1 (enrdf_load_stackoverflow) | 1980-04-25 |
| ES419038A1 (es) | 1976-03-01 |
| SU626675A3 (ru) | 1978-09-30 |
| IL43076A0 (en) | 1973-11-28 |
| IL43076A (en) | 1978-01-31 |
| IT1047948B (it) | 1980-10-20 |
| NL7313245A (enrdf_load_stackoverflow) | 1974-03-28 |
| SU645556A3 (ru) | 1979-01-30 |
| HU169385B (enrdf_load_stackoverflow) | 1976-11-28 |
| JPS49100040A (enrdf_load_stackoverflow) | 1974-09-20 |
| DE2348487A1 (de) | 1974-04-04 |
| FR2201035A1 (enrdf_load_stackoverflow) | 1974-04-26 |
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