GB2058748A - Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives - Google Patents
Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives Download PDFInfo
- Publication number
- GB2058748A GB2058748A GB8017190A GB8017190A GB2058748A GB 2058748 A GB2058748 A GB 2058748A GB 8017190 A GB8017190 A GB 8017190A GB 8017190 A GB8017190 A GB 8017190A GB 2058748 A GB2058748 A GB 2058748A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- salt
- alkyl
- substituted
- thiadiazolyl
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 51
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 25
- 239000013543 active substance Substances 0.000 claims abstract description 28
- 239000004009 herbicide Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 241000196324 Embryophyta Species 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 5
- -1 alkaline-earth metal cation Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 235000009566 rice Nutrition 0.000 claims description 5
- 241000219146 Gossypium Species 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000009973 maize Nutrition 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000021536 Sugar beet Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 230000000885 phytotoxic effect Effects 0.000 abstract description 6
- 230000008635 plant growth Effects 0.000 abstract description 3
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 33
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 239000000729 antidote Substances 0.000 description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 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 6
- 241000209094 Oryza Species 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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- 235000019713 millet Nutrition 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- 235000002769 Pastinaca sativa Nutrition 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
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- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- LDHMAVIPBRSVRG-UHFFFAOYSA-O 1-methylnicotinamide Chemical compound C[N+]1=CC=CC(C(N)=O)=C1 LDHMAVIPBRSVRG-UHFFFAOYSA-O 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 description 1
- HFBHPHBIBAUDNE-UHFFFAOYSA-N 2h-1,2,4-triazin-3-one Chemical class O=C1N=CC=NN1 HFBHPHBIBAUDNE-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
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- 235000006463 Brassica alba Nutrition 0.000 description 1
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- 235000014716 Eleusine indica Nutrition 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
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- 240000001451 Rottboellia cochinchinensis Species 0.000 description 1
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- 230000003042 antagnostic effect Effects 0.000 description 1
- 238000013142 basic testing Methods 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH484179 | 1979-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2058748A true GB2058748A (en) | 1981-04-15 |
Family
ID=4283488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8017190A Withdrawn GB2058748A (en) | 1979-05-23 | 1980-05-23 | Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS55160771A (es) |
| AU (1) | AU5865980A (es) |
| BE (1) | BE883399A (es) |
| DE (1) | DE3019259A1 (es) |
| ES (1) | ES491731A0 (es) |
| FR (1) | FR2457289A1 (es) |
| GB (1) | GB2058748A (es) |
| IL (1) | IL60133A0 (es) |
| IT (1) | IT8022264A0 (es) |
| NL (1) | NL8002944A (es) |
| ZA (1) | ZA803050B (es) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0394043A1 (en) * | 1989-04-19 | 1990-10-24 | Sumitomo Chemical Company, Limited | An amide compound and its production and use |
| US5264448A (en) * | 1989-04-19 | 1993-11-23 | Sumitomo Chemical Company, Limited | Amide compound and its production and use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA01933A (fr) * | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Dérivés du thiazole. |
| DE1670924B2 (de) * | 1967-09-19 | 1976-11-18 | Bayer Ag, 5090 Leverkusen | 1,2,4-thiadiazolyl-harnstoffderivate |
| US3673203A (en) * | 1969-10-22 | 1972-06-27 | Exxon Research Engineering Co | 1,2,4-thiadiazolyl ureas |
| CH549338A (de) * | 1970-03-19 | 1974-05-31 | Agripat Sa | Herbizides mittel. |
| DE2407634A1 (de) * | 1974-02-18 | 1975-08-28 | Bayer Ag | N- eckige klammer auf 3-tert.-butyl-1, 2,4-thiadiazolyl-(5) eckige klammer zu -harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als selektive herbizide |
| DE2745968A1 (de) * | 1977-10-10 | 1979-04-19 | Schering Ag | Mittel zur entblaetterung von pflanzen |
-
1980
- 1980-05-20 IL IL60133A patent/IL60133A0/xx unknown
- 1980-05-20 DE DE19803019259 patent/DE3019259A1/de not_active Withdrawn
- 1980-05-21 NL NL8002944A patent/NL8002944A/nl not_active Application Discontinuation
- 1980-05-21 FR FR8011314A patent/FR2457289A1/fr not_active Withdrawn
- 1980-05-21 BE BE0/200690A patent/BE883399A/fr unknown
- 1980-05-22 ZA ZA00803050A patent/ZA803050B/xx unknown
- 1980-05-22 AU AU58659/80A patent/AU5865980A/en not_active Abandoned
- 1980-05-22 IT IT8022264A patent/IT8022264A0/it unknown
- 1980-05-22 ES ES491731A patent/ES491731A0/es active Granted
- 1980-05-23 GB GB8017190A patent/GB2058748A/en not_active Withdrawn
- 1980-05-23 JP JP6881980A patent/JPS55160771A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0394043A1 (en) * | 1989-04-19 | 1990-10-24 | Sumitomo Chemical Company, Limited | An amide compound and its production and use |
| US5264448A (en) * | 1989-04-19 | 1993-11-23 | Sumitomo Chemical Company, Limited | Amide compound and its production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| BE883399A (fr) | 1980-11-21 |
| DE3019259A1 (de) | 1980-12-04 |
| IL60133A0 (en) | 1980-07-31 |
| ES8104263A1 (es) | 1981-04-16 |
| FR2457289A1 (fr) | 1980-12-19 |
| ZA803050B (en) | 1981-06-24 |
| JPS55160771A (en) | 1980-12-13 |
| IT8022264A0 (it) | 1980-05-22 |
| NL8002944A (nl) | 1980-11-25 |
| ES491731A0 (es) | 1981-04-16 |
| AU5865980A (en) | 1980-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |