IL43887A - Insecticidal and acaricidal compositions containing 1,3-bis-phenyl-2-trichloromethyl-imidazolidines and certain novel compounds of this type - Google Patents
Insecticidal and acaricidal compositions containing 1,3-bis-phenyl-2-trichloromethyl-imidazolidines and certain novel compounds of this typeInfo
- Publication number
- IL43887A IL43887A IL43887A IL4388773A IL43887A IL 43887 A IL43887 A IL 43887A IL 43887 A IL43887 A IL 43887A IL 4388773 A IL4388773 A IL 4388773A IL 43887 A IL43887 A IL 43887A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compositions
- compound
- atom
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 43
- 239000000203 mixture Substances 0.000 title claims description 30
- 230000000895 acaricidal effect Effects 0.000 title claims description 12
- 230000000749 insecticidal effect Effects 0.000 title claims description 10
- BUBTVKILCRRSJO-UHFFFAOYSA-N 1,3-diphenyl-2-(trichloromethyl)imidazolidine Chemical class ClC(Cl)(Cl)C1N(C=2C=CC=CC=2)CCN1C1=CC=CC=C1 BUBTVKILCRRSJO-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- NFQIYHPAGNZAOO-UHFFFAOYSA-N 1,3-bis(3-chlorophenyl)-2-(trichloromethyl)imidazolidine Chemical compound ClC1=CC=CC(N2C(N(CC2)C=2C=C(Cl)C=CC=2)C(Cl)(Cl)Cl)=C1 NFQIYHPAGNZAOO-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 206010061217 Infestation Diseases 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000010410 dusting Methods 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UKGKAYAYAZKNRN-UHFFFAOYSA-N 1,3-bis(3,5-dimethylphenyl)-2-(trichloromethyl)imidazolidine Chemical compound CC1=CC(C)=CC(N2C(N(CC2)C=2C=C(C)C=C(C)C=2)C(Cl)(Cl)Cl)=C1 UKGKAYAYAZKNRN-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000004495 emulsifiable concentrate Substances 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940015043 glyoxal Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- LFMQNMXVVXHZCC-UHFFFAOYSA-N 1,3-benzothiazol-2-yl n,n-diethylcarbamodithioate Chemical compound C1=CC=C2SC(SC(=S)N(CC)CC)=NC2=C1 LFMQNMXVVXHZCC-UHFFFAOYSA-N 0.000 description 1
- WYJKVLRRLPZCPC-UHFFFAOYSA-N 1,3-bis(4-methylphenyl)-2-(trichloromethyl)imidazolidine Chemical compound C1=CC(C)=CC=C1N1C(C(Cl)(Cl)Cl)N(C=2C=CC(C)=CC=2)CC1 WYJKVLRRLPZCPC-UHFFFAOYSA-N 0.000 description 1
- AZINJOAUEDYASP-UHFFFAOYSA-N 1-n,1-n'-diphenylethane-1,1-diamine Chemical class C=1C=CC=CC=1NC(C)NC1=CC=CC=C1 AZINJOAUEDYASP-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical class CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 241001454295 Tetranychidae Species 0.000 description 1
- 101150077854 USE1 gene Proteins 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XLYRTRQTLBKLLD-UHFFFAOYSA-N n'-(3-chlorophenyl)ethane-1,2-diamine Chemical compound NCCNC1=CC=CC(Cl)=C1 XLYRTRQTLBKLLD-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL49112A IL49112A (en) | 1973-12-21 | 1976-02-27 | Imidazolidine derivatives, their preparation and their use as insecticides and acaricides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2263239A DE2263239C3 (de) | 1972-12-23 | 1972-12-23 | Neue Derivate des 2-Trichlormethylimidazolidins, ihre Herstellung und sie enthaltende insektizide und akarizide Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43887A0 IL43887A0 (en) | 1974-03-14 |
| IL43887A true IL43887A (en) | 1977-05-31 |
Family
ID=5865348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43887A IL43887A (en) | 1972-12-23 | 1973-12-21 | Insecticidal and acaricidal compositions containing 1,3-bis-phenyl-2-trichloromethyl-imidazolidines and certain novel compounds of this type |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5820921B2 (cs) |
| BE (1) | BE809042A (cs) |
| CA (1) | CA1100514A (cs) |
| CH (1) | CH587827A5 (cs) |
| CS (1) | CS165314B2 (cs) |
| DD (2) | DD110162A5 (cs) |
| DE (1) | DE2263239C3 (cs) |
| FR (1) | FR2211183B1 (cs) |
| GB (1) | GB1444600A (cs) |
| HU (1) | HU167236B (cs) |
| IL (1) | IL43887A (cs) |
| IT (1) | IT1048292B (cs) |
| NL (1) | NL7317576A (cs) |
| SU (1) | SU547170A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2508715A1 (de) * | 1975-02-28 | 1976-09-09 | Celamerck Gmbh & Co Kg | Insektizide und akarizide wirkstoffe und ihre verwendung |
-
1972
- 1972-12-23 DE DE2263239A patent/DE2263239C3/de not_active Expired
-
1973
- 1973-12-13 SU SU1979274A patent/SU547170A3/ru active
- 1973-12-20 CH CH1792873A patent/CH587827A5/xx not_active IP Right Cessation
- 1973-12-20 GB GB5919373A patent/GB1444600A/en not_active Expired
- 1973-12-21 HU HUCE981A patent/HU167236B/hu unknown
- 1973-12-21 DD DD175607A patent/DD110162A5/xx unknown
- 1973-12-21 CS CS8908A patent/CS165314B2/cs unknown
- 1973-12-21 JP JP744694A patent/JPS5820921B2/ja not_active Expired
- 1973-12-21 NL NL7317576A patent/NL7317576A/xx not_active Application Discontinuation
- 1973-12-21 FR FR7346115A patent/FR2211183B1/fr not_active Expired
- 1973-12-21 DD DD182319*A patent/DD114606A5/xx unknown
- 1973-12-21 IL IL43887A patent/IL43887A/en unknown
- 1973-12-21 BE BE139228A patent/BE809042A/xx not_active IP Right Cessation
- 1973-12-21 CA CA188,750A patent/CA1100514A/en not_active Expired
- 1973-12-21 IT IT54552/73A patent/IT1048292B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2263239B2 (de) | 1981-05-14 |
| GB1444600A (en) | 1976-08-04 |
| SU547170A3 (ru) | 1977-02-15 |
| CS165314B2 (cs) | 1975-12-22 |
| DE2263239C3 (de) | 1982-02-25 |
| NL7317576A (cs) | 1974-06-25 |
| HU167236B (cs) | 1975-09-27 |
| DD110162A5 (cs) | 1974-12-12 |
| JPS5820921B2 (ja) | 1983-04-26 |
| BE809042A (fr) | 1974-06-21 |
| CA1100514A (en) | 1981-05-05 |
| JPS4994836A (cs) | 1974-09-09 |
| FR2211183A1 (cs) | 1974-07-19 |
| DE2263239A1 (de) | 1974-06-27 |
| FR2211183B1 (cs) | 1978-12-01 |
| CH587827A5 (cs) | 1977-05-13 |
| IT1048292B (it) | 1980-11-20 |
| IL43887A0 (en) | 1974-03-14 |
| DD114606A5 (cs) | 1975-08-12 |
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