CA1229605A - 3,4-di-(methylamino)-6-tert-butyl-4,5-dihydro-1,2,4- triazin-5-one - Google Patents
3,4-di-(methylamino)-6-tert-butyl-4,5-dihydro-1,2,4- triazin-5-oneInfo
- Publication number
- CA1229605A CA1229605A CA000445017A CA445017A CA1229605A CA 1229605 A CA1229605 A CA 1229605A CA 000445017 A CA000445017 A CA 000445017A CA 445017 A CA445017 A CA 445017A CA 1229605 A CA1229605 A CA 1229605A
- Authority
- CA
- Canada
- Prior art keywords
- tert
- butyl
- dihydro
- triazin
- methylamino
- 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
- TZHJIUXYXFVNDP-UHFFFAOYSA-N 6-tert-butyl-3,4-bis(methylamino)-1,2,4-triazin-5-one Chemical compound CNC1=NN=C(C(C)(C)C)C(=O)N1NC TZHJIUXYXFVNDP-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 19
- 230000008635 plant growth Effects 0.000 claims abstract description 7
- JBFWXRSTOLHNFZ-UHFFFAOYSA-N 6-tert-butyl-4-(methylamino)-3-methylsulfanyl-1,2,4-triazin-5-one Chemical compound CNN1C(SC)=NN=C(C(C)(C)C)C1=O JBFWXRSTOLHNFZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 29
- -1 methyl halide Chemical class 0.000 claims description 21
- 240000000111 Saccharum officinarum Species 0.000 claims description 19
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- KXEFTYSEZKBQIA-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-(methylamino)-1,2,4-triazin-5-one Chemical compound CNC1=NN=C(C(C)(C)C)C(=O)N1N KXEFTYSEZKBQIA-UHFFFAOYSA-N 0.000 claims description 5
- 244000068988 Glycine max Species 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
- 240000008042 Zea mays Species 0.000 claims description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
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- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 27
- 150000003918 triazines Chemical class 0.000 abstract 3
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- 239000000126 substance Substances 0.000 description 9
- 229920000180 alkyd Polymers 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 239000007921 spray Substances 0.000 description 6
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 241000219144 Abutilon Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000021506 Ipomoea Nutrition 0.000 description 3
- 240000007298 Megathyrsus maximus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 230000009291 secondary effect Effects 0.000 description 3
- 210000000225 synapse Anatomy 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- MYRZHMIBRIKWDO-UHFFFAOYSA-N 4h-triazin-5-one Chemical compound O=C1CN=NN=C1 MYRZHMIBRIKWDO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021532 Calcite Inorganic materials 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 244000047670 Viola x wittrockiana Species 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
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- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical class C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH15083 | 1983-01-12 | ||
| CH150/83-1 | 1983-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1229605A true CA1229605A (en) | 1987-11-24 |
Family
ID=4180388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000445017A Expired CA1229605A (en) | 1983-01-12 | 1984-01-10 | 3,4-di-(methylamino)-6-tert-butyl-4,5-dihydro-1,2,4- triazin-5-one |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE40124T1 (de) * | 1984-01-11 | 1989-02-15 | Ciba Geigy Ag | Herbizide und insektizide triazinone. |
| US5258767A (en) * | 1989-03-14 | 1993-11-02 | Kokusai Denshin Denwa Co., Ltd. | Antenna system for shaped beam |
| US4904762A (en) * | 1989-08-21 | 1990-02-27 | Xerox Corporation | Toner compositions with charge enhancing additives |
| US5932578A (en) | 1996-03-28 | 1999-08-03 | Alteon Inc. | Triazine compounds and methods of use therefor |
| CN119707845A (zh) * | 2024-12-13 | 2025-03-28 | 兰升生物科技集团股份有限公司 | 选择性分离嗪草酮的方法及其分离中间体 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH495110A (de) * | 1966-04-16 | 1970-08-31 | Bayer Ag | Herbizides Mittel |
| US4346220A (en) * | 1966-11-28 | 1982-08-24 | E. I. Du Pont De Nemours And Company | 1,2,4-Triazin-5-ones |
| US3905801A (en) * | 1966-11-28 | 1975-09-16 | Du Pont | Substituted 1,2,4-triazine-5-ones as herbicides |
| DE2165554A1 (de) * | 1971-12-30 | 1973-07-05 | Bayer Ag | Verfahren zur herstellung von 1,2,4triazin-5-on-derivaten |
| FR2482421B1 (fr) * | 1980-05-19 | 1985-08-02 | Slovenska Akademia Vied | Agent permettant d'augmenter la recolte de produits agricoles |
| US4435568A (en) * | 1982-07-22 | 1984-03-06 | E. I. Du Pont De Nemours And Company | Thiol methylation process-reaction, recycle and regeneration of methyl bromide |
-
1984
- 1984-01-06 US US06/568,869 patent/US4547216A/en not_active Expired - Fee Related
- 1984-01-06 GB GB08400250A patent/GB2133011B/en not_active Expired
- 1984-01-06 EP EP84810009A patent/EP0114783B1/de not_active Expired
- 1984-01-06 DE DE8484810009T patent/DE3463141D1/de not_active Expired
- 1984-01-06 AT AT84810009T patent/ATE26574T1/de active
- 1984-01-09 CS CS84179A patent/CS244438B2/cs unknown
- 1984-01-10 GR GR73479A patent/GR81960B/el unknown
- 1984-01-10 CA CA000445017A patent/CA1229605A/en not_active Expired
- 1984-01-10 IL IL70649A patent/IL70649A/xx not_active IP Right Cessation
- 1984-01-10 ZW ZW3/84A patent/ZW384A1/xx unknown
- 1984-01-10 KR KR1019840000067A patent/KR840007403A/ko not_active Ceased
- 1984-01-11 DO DO1984004203A patent/DOP1984004203A/es unknown
- 1984-01-11 AU AU23214/84A patent/AU2321484A/en not_active Abandoned
- 1984-01-11 ZA ZA84220A patent/ZA84220B/xx unknown
- 1984-01-11 BR BR8400127A patent/BR8400127A/pt unknown
- 1984-01-11 ES ES528792A patent/ES8605764A1/es not_active Expired
- 1984-01-12 CU CU8315083-1A patent/CU21591A3/es unknown
- 1984-01-12 JP JP59004214A patent/JPS59134783A/ja active Granted
-
1987
- 1987-12-30 MY MY703/87A patent/MY8700703A/xx unknown
-
1988
- 1988-03-16 PH PH30093A patent/PH21827A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59134783A (ja) | 1984-08-02 |
| DOP1984004203A (es) | 1989-02-17 |
| GR81960B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-12 |
| ATE26574T1 (de) | 1987-05-15 |
| ES528792A0 (es) | 1986-04-01 |
| BR8400127A (pt) | 1984-08-21 |
| AU2321484A (en) | 1984-07-19 |
| PH21827A (en) | 1988-03-16 |
| EP0114783B1 (de) | 1987-04-15 |
| GB2133011A (en) | 1984-07-18 |
| GB2133011B (en) | 1986-07-16 |
| CS244438B2 (en) | 1986-07-17 |
| IL70649A (en) | 1987-03-31 |
| ZA84220B (en) | 1984-09-26 |
| IL70649A0 (en) | 1984-04-30 |
| US4547216A (en) | 1985-10-15 |
| GB8400250D0 (en) | 1984-02-08 |
| DE3463141D1 (en) | 1987-05-21 |
| ES8605764A1 (es) | 1986-04-01 |
| EP0114783A1 (de) | 1984-08-01 |
| ZW384A1 (en) | 1984-08-08 |
| CU21591A3 (en) | 1987-07-22 |
| JPS6221349B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-12 |
| KR840007403A (ko) | 1984-12-07 |
| MY8700703A (en) | 1987-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |