DE1567218C3 - Verwendung von 4-Chlorphenoxyessigsäureamid-Derivaten als Herbizide - Google Patents
Verwendung von 4-Chlorphenoxyessigsäureamid-Derivaten als HerbizideInfo
- Publication number
- DE1567218C3 DE1567218C3 DE19631567218 DE1567218A DE1567218C3 DE 1567218 C3 DE1567218 C3 DE 1567218C3 DE 19631567218 DE19631567218 DE 19631567218 DE 1567218 A DE1567218 A DE 1567218A DE 1567218 C3 DE1567218 C3 DE 1567218C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- damage
- methoxy
- plants
- compounds
- 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
- 239000004009 herbicide Substances 0.000 title description 12
- RHLHDNNWVXMDAF-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetamide Chemical class NC(=O)COC1=CC=C(Cl)C=C1 RHLHDNNWVXMDAF-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- 241000196324 Embryophyta Species 0.000 description 56
- 230000006378 damage Effects 0.000 description 23
- 230000002363 herbicidal effect Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- -1 phenoxyacetic acid halide Chemical class 0.000 description 11
- 241001520106 Eustachys Species 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000005474 African couch grass Nutrition 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 7
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 7
- 230000009528 severe injury Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000013068 control sample Substances 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- 235000013603 Digitaria ischaemum Nutrition 0.000 description 4
- 241001426056 Eleusine coracana subsp. coracana Species 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- ASRSBXRMOCLKQC-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-methoxyacetamide Chemical compound CONC(=O)COC1=CC=C(Cl)C=C1C ASRSBXRMOCLKQC-UHFFFAOYSA-N 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000009526 moderate injury Effects 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 230000017074 necrotic cell death Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ANJBGAQSEFAAMV-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)COC1=CC=C(Cl)C=C1C ANJBGAQSEFAAMV-UHFFFAOYSA-N 0.000 description 2
- BZMCWLGUXMFYNU-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)COC1=CC=C(Cl)C=C1 BZMCWLGUXMFYNU-UHFFFAOYSA-N 0.000 description 2
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 2
- 240000002245 Acer pensylvanicum Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000078127 Eleusine coracana Species 0.000 description 2
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 2
- 244000248416 Fagopyrum cymosum Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 241000427250 Moehringia Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000005262 alkoxyamine group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000003673 groundwater Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- UXPQIWRVOJGVQX-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-ethoxyacetamide Chemical compound CCONC(=O)COC1=CC=C(Cl)C=C1C UXPQIWRVOJGVQX-UHFFFAOYSA-N 0.000 description 1
- JQFRGTHNLRXLLD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-methoxyacetamide Chemical compound CONC(=O)COC1=CC=C(Cl)C=C1 JQFRGTHNLRXLLD-UHFFFAOYSA-N 0.000 description 1
- 240000000321 Abutilon grandifolium Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000803625 Andropogon virginicus Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 240000008399 Barbarea vulgaris Species 0.000 description 1
- 235000007563 Barbarea vulgaris Nutrition 0.000 description 1
- 241001148684 Bothriochloa ischaemum Species 0.000 description 1
- 241000219477 Bougainvillea glabra Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 241000209202 Bromus secalinus Species 0.000 description 1
- PDMRNUBRHJAMIN-UHFFFAOYSA-N CN(C(C(Cl)(Cl)Cl)=O)OC Chemical compound CN(C(C(Cl)(Cl)Cl)=O)OC PDMRNUBRHJAMIN-UHFFFAOYSA-N 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 235000010856 Cirsium lanceolatum Nutrition 0.000 description 1
- 244000272323 Cirsium lanceolatum Species 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 235000004266 Cynoglossum officinale Nutrition 0.000 description 1
- 240000004487 Cynoglossum officinale Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002206 Daucus carota subsp carota Nutrition 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000009967 Erodium cicutarium Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 240000008077 Ruellia tuberosa Species 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- 235000015761 Rumex acetosella Nutrition 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 240000007807 Sisymbrium officinale Species 0.000 description 1
- 235000015503 Sorghum bicolor subsp. drummondii Nutrition 0.000 description 1
- 244000064817 Sorghum halepense var. sudanense Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 240000008488 Thlaspi arvense Species 0.000 description 1
- 235000008214 Thlaspi arvense Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000005770 birds nest Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000036253 epinasty Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- LUKNLVTZDZMBOU-UHFFFAOYSA-N n-ethoxymethanamine Chemical compound CCONC LUKNLVTZDZMBOU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxy-acetic acid Natural products OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 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
- 235000005345 purple finger grass Nutrition 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US239071A US3166589A (en) | 1962-11-20 | 1962-11-20 | Phenoxyacetamides for the control of pests |
| US239072A US3166591A (en) | 1962-11-20 | 1962-11-20 | Phenoxyacetamides for the control of pests |
| US239070A US3168561A (en) | 1962-11-20 | 1962-11-20 | N-alkoxy 2-alkyl-4-chlorophenoxyacetamides for the control of pests |
| US271869A US3352897A (en) | 1963-04-10 | 1963-04-10 | Nu-alkoxy amides of 4-halophenoxyalkylcarboxy acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1567218A1 DE1567218A1 (de) | 1972-03-30 |
| DE1567218B2 DE1567218B2 (de) | 1973-02-22 |
| DE1567218C3 true DE1567218C3 (de) | 1973-09-27 |
Family
ID=27499960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631567218 Expired DE1567218C3 (de) | 1962-11-20 | 1963-11-18 | Verwendung von 4-Chlorphenoxyessigsäureamid-Derivaten als Herbizide |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE640201A (enExample) |
| CH (1) | CH442863A (enExample) |
| DE (1) | DE1567218C3 (enExample) |
| GB (1) | GB1038184A (enExample) |
| NL (1) | NL300504A (enExample) |
-
0
- NL NL300504D patent/NL300504A/xx unknown
-
1963
- 1963-11-07 GB GB4403663A patent/GB1038184A/en not_active Expired
- 1963-11-18 DE DE19631567218 patent/DE1567218C3/de not_active Expired
- 1963-11-19 CH CH1415663A patent/CH442863A/de unknown
- 1963-11-20 BE BE640201A patent/BE640201A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH442863A (de) | 1967-08-31 |
| DE1567218A1 (de) | 1972-03-30 |
| NL300504A (enExample) | |
| GB1038184A (en) | 1966-08-10 |
| BE640201A (enExample) | 1964-05-20 |
| DE1567218B2 (de) | 1973-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |