NO134051B - - Google Patents
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- Publication number
- NO134051B NO134051B NO478/72A NO47872A NO134051B NO 134051 B NO134051 B NO 134051B NO 478/72 A NO478/72 A NO 478/72A NO 47872 A NO47872 A NO 47872A NO 134051 B NO134051 B NO 134051B
- Authority
- NO
- Norway
- Prior art keywords
- atoms
- alkyl
- phenyl
- formula
- means hydrogen
- Prior art date
Links
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000002429 hydrazines Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- GAIDCDVTAJLEAE-UHFFFAOYSA-N 4-amino-1,2,4-triazin-5-one Chemical class NN1C=NN=CC1=O GAIDCDVTAJLEAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 11
- -1 t-butylglyoxylic acid methyl ester-2-propionyl-hydrazone Chemical compound 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 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 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000007351 Eleusine Nutrition 0.000 description 2
- 241000209215 Eleusine Species 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000219422 Urtica Species 0.000 description 2
- 235000009108 Urtica dioica Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QFFUHJDDEGKIJW-UHFFFAOYSA-N methyl 2-(cyclohexanecarbonylhydrazinylidene)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)=NNC(=O)C1CCCCC1 QFFUHJDDEGKIJW-UHFFFAOYSA-N 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BOUIZPWBFIVJPD-UHFFFAOYSA-N 3h-1,2,4-triazin-4-amine Chemical compound NN1CN=NC=C1 BOUIZPWBFIVJPD-UHFFFAOYSA-N 0.000 description 1
- IRBORRDVQOVFCT-UHFFFAOYSA-N 4-amino-3-cyclohexyl-6-phenyl-1,2,4-triazin-5-one Chemical compound O=C1N(N)C(C2CCCCC2)=NN=C1C1=CC=CC=C1 IRBORRDVQOVFCT-UHFFFAOYSA-N 0.000 description 1
- KQVCLOPDOWDNRV-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethyl-1,2,4-triazin-5-one Chemical compound CCC1=NN=C(C(C)(C)C)C(=O)N1N KQVCLOPDOWDNRV-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241001456088 Hesperocnide Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000017879 Nasturtium officinale Nutrition 0.000 description 1
- 240000005407 Nasturtium officinale Species 0.000 description 1
- 241000830116 Orbexilum onobrychis Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001479578 Packera contermina Species 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000005601 Trisetum Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HUYREUUJFLHEDE-UHFFFAOYSA-N cyclohexanecarbohydrazide Chemical compound NNC(=O)C1CCCCC1 HUYREUUJFLHEDE-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- NRXFOYAHMBPJEP-UHFFFAOYSA-N methyl 3,3-dimethyl-2-oxobutanoate Chemical compound COC(=O)C(=O)C(C)(C)C NRXFOYAHMBPJEP-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 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
- 238000003892 spreading Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2107757A DE2107757C3 (de) | 1971-02-18 | 1971-02-18 | 4-Amino-1,2,4-triazin-5-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134051B true NO134051B (ja) | 1976-05-03 |
| NO134051C NO134051C (ja) | 1976-08-11 |
Family
ID=5799135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO47872A NO134051C (ja) | 1971-02-18 | 1972-02-17 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3847914A (ja) |
| JP (2) | JPS5641602B1 (ja) |
| AT (2) | AT320343B (ja) |
| BE (1) | BE779572A (ja) |
| BG (2) | BG19086A3 (ja) |
| BR (1) | BR7200897D0 (ja) |
| CA (1) | CA996110A (ja) |
| CH (1) | CH565777A5 (ja) |
| CS (1) | CS170177B2 (ja) |
| CY (1) | CY864A (ja) |
| DD (1) | DD100258A5 (ja) |
| DE (1) | DE2107757C3 (ja) |
| DK (1) | DK133983C (ja) |
| EG (1) | EG10756A (ja) |
| FI (1) | FI53818C (ja) |
| FR (1) | FR2126892A5 (ja) |
| GB (1) | GB1331739A (ja) |
| GT (1) | GT198062782A (ja) |
| HU (1) | HU163832B (ja) |
| IL (1) | IL38767A (ja) |
| IT (1) | IT954888B (ja) |
| MY (1) | MY7400109A (ja) |
| NL (1) | NL175489C (ja) |
| NO (1) | NO134051C (ja) |
| PL (1) | PL74942B1 (ja) |
| RO (1) | RO58639A (ja) |
| SE (1) | SE389113B (ja) |
| SU (1) | SU431674A3 (ja) |
| TR (1) | TR17828A (ja) |
| YU (1) | YU35885B (ja) |
| ZA (1) | ZA721044B (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE786840A (fr) * | 1971-07-29 | 1973-01-29 | Bayer Ag | Procede de preparation de 1,2,4-triazine -5-ones |
| DE2224161A1 (de) * | 1972-05-18 | 1973-11-29 | Bayer Ag | Selektiv herbizide mittel |
| DE2238206C2 (de) * | 1972-08-03 | 1985-05-02 | Bayer Ag, 5090 Leverkusen | Azomethine von 4-Amino-5-H-1,2,4-triazin-5-onen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide |
| DE2346936C2 (de) * | 1973-09-18 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen 3,4-Dihydro-1,2,4-triazinen sowie drei Verbindungen dieses Typs und deren Verwendung |
| US4057546A (en) * | 1973-12-24 | 1977-11-08 | Bayer Aktiengesellschaft | 4-Amino-1,2,4-triazin-5-ones |
| DE2417511A1 (de) * | 1974-04-10 | 1975-10-30 | Bayer Ag | 6-sec.-butyl-1,2,4-triazin-5(4h)-one, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| US4140517A (en) * | 1974-11-18 | 1979-02-20 | Basf Aktiengesellschaft | Herbicidal compositions |
| GR65206B (en) * | 1977-07-20 | 1980-07-29 | Ciba Geigy Ag | Herbicidal derivative of 1,2,4-briazin-5-ons |
| FR2482421B1 (fr) * | 1980-05-19 | 1985-08-02 | Slovenska Akademia Vied | Agent permettant d'augmenter la recolte de produits agricoles |
| DE3238007A1 (de) * | 1982-10-13 | 1984-04-19 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von triazinon- und triazindion-derivaten |
| US4820336A (en) * | 1987-01-07 | 1989-04-11 | E. I. Du Pont De Nemours And Company | Herbicidal spray mixtures |
| JPS63172602A (ja) * | 1987-08-17 | 1988-07-16 | 宮脇 卯一 | 横引用手挽鋸 |
| DE3833801A1 (de) * | 1988-10-05 | 1990-04-12 | Bayer Ag | Selektiv-herbizide mittel, enthaltend metamitron in kombination mit bestimmten triazolinonen |
-
1971
- 1971-02-18 DE DE2107757A patent/DE2107757C3/de not_active Expired
-
1972
- 1972-02-09 EG EG4972A patent/EG10756A/xx active
- 1972-02-09 US US22496672 patent/US3847914A/en not_active Expired - Lifetime
- 1972-02-11 YU YU33872A patent/YU35885B/xx unknown
- 1972-02-14 BG BG2077372A patent/BG19086A3/xx unknown
- 1972-02-14 BG BG1971772A patent/BG18872A3/xx unknown
- 1972-02-15 NL NL7201966A patent/NL175489C/xx not_active IP Right Cessation
- 1972-02-15 CS CS95272A patent/CS170177B2/cs unknown
- 1972-02-15 TR TR1782872A patent/TR17828A/xx unknown
- 1972-02-15 IL IL38767A patent/IL38767A/en unknown
- 1972-02-16 IT IT2064872Q patent/IT954888B/it active
- 1972-02-16 SU SU1749597A patent/SU431674A3/ru active
- 1972-02-16 DD DD16091272A patent/DD100258A5/xx unknown
- 1972-02-16 RO RO6978272A patent/RO58639A/ro unknown
- 1972-02-16 CH CH220672A patent/CH565777A5/xx not_active IP Right Cessation
- 1972-02-16 FI FI41772A patent/FI53818C/fi active
- 1972-02-17 ZA ZA721044A patent/ZA721044B/xx unknown
- 1972-02-17 DK DK75572A patent/DK133983C/da active
- 1972-02-17 PL PL1972153537A patent/PL74942B1/pl unknown
- 1972-02-17 NO NO47872A patent/NO134051C/no unknown
- 1972-02-17 GB GB743472A patent/GB1331739A/en not_active Expired
- 1972-02-17 CY CY86472A patent/CY864A/xx unknown
- 1972-02-17 CA CA134,903A patent/CA996110A/en not_active Expired
- 1972-02-17 SE SE193572A patent/SE389113B/xx unknown
- 1972-02-18 BR BR89772A patent/BR7200897D0/pt unknown
- 1972-02-18 FR FR7205547A patent/FR2126892A5/fr not_active Expired
- 1972-02-18 BE BE779572A patent/BE779572A/xx not_active IP Right Cessation
- 1972-02-18 JP JP1654372A patent/JPS5641602B1/ja active Pending
- 1972-02-18 AT AT00633/73A patent/AT320343B/de not_active Expired - Lifetime
- 1972-02-18 AT AT133172A patent/AT311990B/de not_active IP Right Cessation
- 1972-02-18 HU HUBA002704 patent/HU163832B/hu unknown
- 1972-02-18 JP JP1654272A patent/JPS5626665B1/ja active Pending
-
1974
- 1974-12-30 MY MY7400109A patent/MY7400109A/xx unknown
-
1980
- 1980-03-28 GT GT198062782A patent/GT198062782A/es unknown
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