HRP930192A2 - Process for the preparation and use of herbicide n-cyanopyridazinone, as as of herbicidal preparations containing n-cyanopyridazinones - Google Patents
Process for the preparation and use of herbicide n-cyanopyridazinone, as as of herbicidal preparations containing n-cyanopyridazinones Download PDFInfo
- Publication number
- HRP930192A2 HRP930192A2 HR930192A HRP930192A HRP930192A2 HR P930192 A2 HRP930192 A2 HR P930192A2 HR 930192 A HR930192 A HR 930192A HR P930192 A HRP930192 A HR P930192A HR P930192 A2 HRP930192 A2 HR P930192A2
- Authority
- HR
- Croatia
- Prior art keywords
- halogen
- alkyl
- cyanopyridazinones
- cyanopyridazinone
- general formula
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 14
- 239000004009 herbicide Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- OBKLQOOUWUPYQC-UHFFFAOYSA-N 6-oxo-1,5-dihydropyridazine-2-carbonitrile Chemical class O=C1CC=CN(C#N)N1 OBKLQOOUWUPYQC-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- -1 halogen cyanide Chemical class 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000003701 inert diluent Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- CPZLKSSMZLLSBN-UHFFFAOYSA-N 6-oxo-1h-pyridazine-5-carbonitrile Chemical compound O=C1NN=CC=C1C#N CPZLKSSMZLLSBN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- FNHIHTYRIMDIMS-UHFFFAOYSA-N [Br+].[C-]#N Chemical compound [Br+].[C-]#N FNHIHTYRIMDIMS-UHFFFAOYSA-N 0.000 claims 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 1
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 239000007787 solid Substances 0.000 description 16
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- 239000000203 mixture Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 239000005995 Aluminium silicate Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 240000004385 Centaurea cyanus Species 0.000 description 3
- 235000005940 Centaurea cyanus Nutrition 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
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- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000004113 Sepiolite Substances 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
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 240000000359 Triticum dicoccon Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- RUJZOLJJMYOMCV-UHFFFAOYSA-N [(6-chloro-3-phenylpyridazin-4-yl)-octyl-$l^{4}-sulfanylidene]methanediol Chemical compound CCCCCCCCS(=C(O)O)C1=CC(Cl)=NN=C1C1=CC=CC=C1 RUJZOLJJMYOMCV-UHFFFAOYSA-N 0.000 description 1
- YBGJZYCWGNYUMA-UHFFFAOYSA-M [Cl-].[P+]=O Chemical compound [Cl-].[P+]=O YBGJZYCWGNYUMA-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
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- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
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- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000001117 oleyl group Polymers [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])=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])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 229910052682 stishovite Inorganic materials 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
- 239000003784 tall oil Substances 0.000 description 1
- 239000011273 tar residue Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings 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
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings 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
- C07D237/14—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0025892A AT397085B (de) | 1992-02-17 | 1992-02-17 | Herbizide n-cyanopyridazinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP930192A2 true HRP930192A2 (en) | 1995-12-31 |
Family
ID=3485763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR930192A HRP930192A2 (en) | 1992-02-17 | 1993-02-16 | Process for the preparation and use of herbicide n-cyanopyridazinone, as as of herbicidal preparations containing n-cyanopyridazinones |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5462914A (lv) |
| EP (1) | EP0556647A1 (lv) |
| JP (1) | JPH069574A (lv) |
| KR (1) | KR930017878A (lv) |
| CN (1) | CN1075477A (lv) |
| AT (1) | AT397085B (lv) |
| AU (1) | AU647687B2 (lv) |
| BG (1) | BG97448A (lv) |
| BR (1) | BR9300589A (lv) |
| CA (1) | CA2089451A1 (lv) |
| CZ (1) | CZ19693A3 (lv) |
| EE (1) | EE9400149A (lv) |
| HR (1) | HRP930192A2 (lv) |
| HU (1) | HUT64042A (lv) |
| IL (1) | IL104449A0 (lv) |
| JO (1) | JO1744B1 (lv) |
| LV (1) | LV10152A (lv) |
| MA (1) | MA22803A1 (lv) |
| MD (1) | MD940047A (lv) |
| MX (1) | MX9300855A (lv) |
| NZ (1) | NZ245706A (lv) |
| PL (1) | PL297750A1 (lv) |
| RO (1) | RO108239B1 (lv) |
| SI (1) | SI9300085A (lv) |
| SK (1) | SK9593A3 (lv) |
| TR (1) | TR26712A (lv) |
| TW (1) | TW221369B (lv) |
| ZA (1) | ZA93648B (lv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506228A (en) * | 1995-02-23 | 1996-04-09 | Merck & Co., Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| US5670504A (en) * | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| WO1999001436A1 (fr) * | 1997-07-01 | 1999-01-14 | Mitsubishi Chemical Corporation | Derives de 3-(phenyle substitue)-4-halopyridazine, pesticides les contenant en tant qu'ingredients actifs et leurs intermediaires |
| US9212146B2 (en) | 2008-03-18 | 2015-12-15 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Substituted pyridazinones for the treatment of tumors |
| CN101537006B (zh) * | 2008-03-18 | 2012-06-06 | 中国科学院上海药物研究所 | 哒嗪酮类化合物在制备抗肿瘤药物中的用途 |
| CN106316962B (zh) * | 2015-07-01 | 2020-03-10 | 中国科学院上海有机化学研究所 | 3-芳基哒嗪酮类化合物、制备方法、农药组合物及用途 |
| CN106831600B (zh) * | 2017-03-03 | 2019-04-12 | 常州沃腾化工科技有限公司 | 3-苯基-4-6-二氯哒嗪的制备方法 |
| CN110128352A (zh) * | 2018-02-02 | 2019-08-16 | 青岛清原化合物有限公司 | 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
| WO2019149260A1 (zh) * | 2018-02-02 | 2019-08-08 | 青岛清原化合物有限公司 | 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2741615A (en) * | 1952-11-22 | 1956-04-10 | Merck & Co Inc | N-substituted dihydrodesoxynorcodeine compounds |
| AT237962B (de) * | 1962-11-10 | 1965-01-25 | Chemie Linz Ag | Selektiv wirkendes, herbizides Mittel |
| DE2229758A1 (de) * | 1972-06-19 | 1974-01-17 | Lentia Gmbh | Neue pyridazinverbindungen, ihre herstellung und verwendung |
| AT334133B (de) * | 1974-12-17 | 1976-12-27 | Chemie Linz Ag | Herbizides mittel |
| US3967952A (en) * | 1975-07-03 | 1976-07-06 | Eli Lilly And Company | 3,5-Diphenyl-4(1H)-pyridazinones(thiones) |
| US4013658A (en) * | 1975-07-03 | 1977-03-22 | Eli Lilly And Company | Synthesis of 3,5-diphenyl-4(1h)-pyridazinones |
| US4732603A (en) * | 1980-10-03 | 1988-03-22 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| JPS63264575A (ja) * | 1987-04-20 | 1988-11-01 | Daicel Chem Ind Ltd | フエノキシピリダジン誘導体、その製造法ならびに植物生長調整剤および除草剤組成物 |
| FR2634199B1 (fr) * | 1988-07-13 | 1990-09-14 | Rhone Poulenc Agrochimie | Composes herbicides et les compositions les contenant |
| AT397598B (de) * | 1990-04-05 | 1994-05-25 | Agrolinz Agrarchemikalien | Herbizides mittel |
| DE4013734A1 (de) * | 1990-04-28 | 1991-10-31 | Agrolinz Agrarchemikalien Muen | Herbizides mittel |
-
1992
- 1992-02-17 AT AT0025892A patent/AT397085B/de not_active IP Right Cessation
-
1993
- 1993-01-19 NZ NZ245706A patent/NZ245706A/en unknown
- 1993-01-20 IL IL104449A patent/IL104449A0/xx unknown
- 1993-01-29 ZA ZA93648A patent/ZA93648B/xx unknown
- 1993-01-29 TW TW082100534A patent/TW221369B/zh active
- 1993-02-04 EP EP93101695A patent/EP0556647A1/de not_active Withdrawn
- 1993-02-10 TR TR93/0138A patent/TR26712A/xx unknown
- 1993-02-12 AU AU33028/93A patent/AU647687B2/en not_active Ceased
- 1993-02-12 CA CA002089451A patent/CA2089451A1/en not_active Abandoned
- 1993-02-15 BG BG97448A patent/BG97448A/xx unknown
- 1993-02-15 RO RO93-00185A patent/RO108239B1/ro unknown
- 1993-02-15 KR KR1019930002038A patent/KR930017878A/ko not_active Application Discontinuation
- 1993-02-15 CZ CZ93196A patent/CZ19693A3/cs unknown
- 1993-02-16 JO JO19931744A patent/JO1744B1/en active
- 1993-02-16 PL PL29775093A patent/PL297750A1/xx unknown
- 1993-02-16 HU HU9300425A patent/HUT64042A/hu unknown
- 1993-02-16 MA MA23096A patent/MA22803A1/fr unknown
- 1993-02-16 JP JP5027000A patent/JPH069574A/ja not_active Withdrawn
- 1993-02-16 HR HR930192A patent/HRP930192A2/hr not_active Application Discontinuation
- 1993-02-16 LV LV930121A patent/LV10152A/lv unknown
- 1993-02-16 SK SK9593A patent/SK9593A3/sk unknown
- 1993-02-16 BR BR9300589A patent/BR9300589A/pt not_active Application Discontinuation
- 1993-02-16 CN CN93101027A patent/CN1075477A/zh active Pending
- 1993-02-17 SI SI19939300085A patent/SI9300085A/sl unknown
- 1993-02-17 MX MX9300855A patent/MX9300855A/es unknown
-
1994
- 1994-02-15 MD MD94-0047A patent/MD940047A/ro not_active Application Discontinuation
- 1994-04-01 US US08/221,464 patent/US5462914A/en not_active Expired - Fee Related
- 1994-11-22 EE EE9400149A patent/EE9400149A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT64042A (en) | 1993-11-29 |
| CZ19693A3 (en) | 1994-01-19 |
| MA22803A1 (fr) | 1993-10-01 |
| RO108239B1 (ro) | 1994-03-31 |
| AT397085B (de) | 1994-01-25 |
| MD940047A (ro) | 1995-08-31 |
| HU9300425D0 (en) | 1993-05-28 |
| BG97448A (en) | 1994-03-24 |
| SI9300085A (en) | 1993-09-30 |
| ATA25892A (de) | 1993-06-15 |
| LV10152A (lv) | 1994-10-20 |
| SK9593A3 (en) | 1993-09-09 |
| EP0556647A1 (de) | 1993-08-25 |
| NZ245706A (en) | 1994-11-25 |
| JPH069574A (ja) | 1994-01-18 |
| IL104449A0 (en) | 1993-05-13 |
| PL297750A1 (en) | 1993-11-02 |
| MX9300855A (es) | 1993-08-01 |
| EE9400149A (et) | 1995-12-15 |
| AU3302893A (en) | 1993-08-19 |
| BR9300589A (pt) | 1993-08-24 |
| JO1744B1 (en) | 1993-10-30 |
| KR930017878A (ko) | 1993-09-20 |
| US5462914A (en) | 1995-10-31 |
| TW221369B (lv) | 1994-03-01 |
| CN1075477A (zh) | 1993-08-25 |
| TR26712A (tr) | 1995-05-15 |
| ZA93648B (en) | 1993-09-02 |
| AU647687B2 (en) | 1994-03-24 |
| CA2089451A1 (en) | 1993-08-18 |
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