AT397085B - Herbizide n-cyanopyridazinone - Google Patents
Herbizide n-cyanopyridazinone Download PDFInfo
- Publication number
- AT397085B AT397085B AT0025892A AT25892A AT397085B AT 397085 B AT397085 B AT 397085B AT 0025892 A AT0025892 A AT 0025892A AT 25892 A AT25892 A AT 25892A AT 397085 B AT397085 B AT 397085B
- Authority
- AT
- Austria
- Prior art keywords
- halogen
- general formula
- cyanopyridazinones
- compound
- alkoxy
- Prior art date
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- OBKLQOOUWUPYQC-UHFFFAOYSA-N 6-oxo-1,5-dihydropyridazine-2-carbonitrile Chemical compound O=C1CC=CN(C#N)N1 OBKLQOOUWUPYQC-UHFFFAOYSA-N 0.000 title claims description 18
- 239000004009 herbicide Substances 0.000 title claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- -1 cyanogen halide Chemical class 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 230000002363 herbicidal effect Effects 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-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
- 239000000969 carrier Substances 0.000 claims description 8
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 claims description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
- 241000196324 Embryophyta Species 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 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
- 229940125782 compound 2 Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 4
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920001732 Lignosulfonate Polymers 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
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- 238000005554 pickling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- 239000004563 wettable powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCKJSOZZDMZSAZ-UHFFFAOYSA-N 4,6-dimethoxy-3-phenylpyridazine Chemical compound N1=NC(OC)=CC(OC)=C1C1=CC=CC=C1 ZCKJSOZZDMZSAZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 240000004385 Centaurea cyanus Species 0.000 description 3
- 235000005940 Centaurea cyanus Nutrition 0.000 description 3
- 240000006122 Chenopodium album Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
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- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- VXYFQWYDZAGOFW-UHFFFAOYSA-N 4,6-dibutoxy-3-phenylpyridazine Chemical compound N1=NC(OCCCC)=CC(OCCCC)=C1C1=CC=CC=C1 VXYFQWYDZAGOFW-UHFFFAOYSA-N 0.000 description 2
- DMRRPUPJQYXOHA-UHFFFAOYSA-N 6-methoxy-3-phenyl-1h-pyridazin-4-one Chemical compound N1=NC(OC)=CC(O)=C1C1=CC=CC=C1 DMRRPUPJQYXOHA-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
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- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 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
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 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
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 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
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- WPBXOELOQKLBDF-UHFFFAOYSA-N cyanogen iodide Chemical compound IC#N WPBXOELOQKLBDF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000000354 decomposition reaction Methods 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 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
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000000227 grinding Methods 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
- 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
- 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
- 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal 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
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 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
- 125000004433 nitrogen atom Chemical group 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
- 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye 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
- 238000012805 post-processing Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 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
- 239000000376 reactant Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000011435 rock 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
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 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
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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
- C07D237/16—Two oxygen atoms
-
- 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)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0025892A AT397085B (de) | 1992-02-17 | 1992-02-17 | Herbizide n-cyanopyridazinone |
| NZ245706A NZ245706A (en) | 1992-02-17 | 1993-01-19 | N-cyanopyridazinone derivatives; preparation, and herbicidal compositions thereof |
| IL104449A IL104449A0 (en) | 1992-02-17 | 1993-01-20 | N-cyanopyridazinones,their preparation and their use as herbicides |
| ZA93648A ZA93648B (en) | 1992-02-17 | 1993-01-29 | Herbicidal N-cyanopyridazinones. |
| TW082100534A TW221369B (en, 2012) | 1992-02-17 | 1993-01-29 | |
| EP93101695A EP0556647A1 (de) | 1992-02-17 | 1993-02-04 | Herbizide N-Cyanopyridazinone |
| TR93/0138A TR26712A (tr) | 1992-02-17 | 1993-02-10 | HERBISIDAL ETKISI OLAN YENI N-ISYANOPIRIDAZINONLAR VE BUNLARIN üRETILMESINE MAHSUS BIR USUL. |
| AU33028/93A AU647687B2 (en) | 1992-02-17 | 1993-02-12 | Herbicidal N-cyanopyridazinones |
| CA002089451A CA2089451A1 (en) | 1992-02-17 | 1993-02-12 | Herbicidal n-cyanopyridazinones |
| KR1019930002038A KR930017878A (ko) | 1992-02-17 | 1993-02-15 | 제초성 n-시아노피리다진온, 이의 제조방법 및 이를 포함하는 제초 조성물 |
| CZ93196A CZ19693A3 (en) | 1992-02-17 | 1993-02-15 | N-cyanopyridazinone derivatives, process for preparing thereof and herbicidal agents in which said derivatives are comprised |
| BG97448A BG97448A (en) | 1992-02-17 | 1993-02-15 | Herbicidal n-cyanopyridazinones |
| RO93-00185A RO108239B1 (ro) | 1992-02-17 | 1993-02-15 | Derivati de n-cianopiridazinona, procedeu pentru prepararea acestora si compozitii erbicide, care ii contin |
| PL29775093A PL297750A1 (en) | 1992-02-17 | 1993-02-16 | Herbicidal n-cyanopyridazinones |
| SK9593A SK9593A3 (en) | 1992-02-17 | 1993-02-16 | N-cyanopyridazine derivatives, process for their preparation and their pharmaceutical compositions |
| MA23096A MA22803A1 (fr) | 1992-02-17 | 1993-02-16 | N-cyanopyridazinones herbicides. |
| CN93101027A CN1075477A (zh) | 1992-02-17 | 1993-02-16 | 具除草活性的n-氰基哒嗪酮 |
| JP5027000A JPH069574A (ja) | 1992-02-17 | 1993-02-16 | 除草性ｎ−シアノピリダジノン |
| JO19931744A JO1744B1 (en) | 1992-02-17 | 1993-02-16 | N-herbicide cyanopyridazine |
| BR9300589A BR9300589A (pt) | 1992-02-17 | 1993-02-16 | N-cianopiridazinonas,processo para sua preparacao,composicao herbicida e processos para a preparacao de composicoes e para o combate de ervas daninhas |
| 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 |
| HU9300425A HUT64042A (en) | 1992-02-17 | 1993-02-16 | N-cyanopyridazinone derivatves, herbicidal compositions comprising such compounds as active ingredient, as well as process for producing and using the active ingredients and the compositions |
| LV930121A LV10152A (lv) | 1992-02-17 | 1993-02-16 | N-cianopiridazinoni ar herbicidu ipasibam |
| MX9300855A MX9300855A (es) | 1992-02-17 | 1993-02-17 | N-cianopiridazinonas, procedimiento para obtenerlas y composiciones herbicidas que las contienen. |
| SI19939300085A SI9300085A (en) | 1992-02-17 | 1993-02-17 | Herbicidal n-cyanopyridazinones |
| MD94-0047A MD940047A (ro) | 1992-02-17 | 1994-02-15 | N-cianopiridacinone, procedeu de obţinere a lor, substanţă erbicidă, procedeu de obţinere a ei, procedeu de combatere a buruienilor |
| US08/221,464 US5462914A (en) | 1992-02-17 | 1994-04-01 | Herbicidal n-cyanopyridazinones |
| EE9400149A EE9400149A (et) | 1992-02-17 | 1994-11-22 | N- tsüanopüriidasioonid, meetod nende valmistamiseks ja herbitsiidid ning nende valmistamise ja kasutamise meetod |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0025892A AT397085B (de) | 1992-02-17 | 1992-02-17 | Herbizide n-cyanopyridazinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA25892A ATA25892A (de) | 1993-06-15 |
| AT397085B true AT397085B (de) | 1994-01-25 |
Family
ID=3485763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0025892A AT397085B (de) | 1992-02-17 | 1992-02-17 | Herbizide n-cyanopyridazinone |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5462914A (en, 2012) |
| EP (1) | EP0556647A1 (en, 2012) |
| JP (1) | JPH069574A (en, 2012) |
| KR (1) | KR930017878A (en, 2012) |
| CN (1) | CN1075477A (en, 2012) |
| AT (1) | AT397085B (en, 2012) |
| AU (1) | AU647687B2 (en, 2012) |
| BG (1) | BG97448A (en, 2012) |
| BR (1) | BR9300589A (en, 2012) |
| CA (1) | CA2089451A1 (en, 2012) |
| CZ (1) | CZ19693A3 (en, 2012) |
| EE (1) | EE9400149A (en, 2012) |
| HR (1) | HRP930192A2 (en, 2012) |
| HU (1) | HUT64042A (en, 2012) |
| IL (1) | IL104449A0 (en, 2012) |
| JO (1) | JO1744B1 (en, 2012) |
| LV (1) | LV10152A (en, 2012) |
| MA (1) | MA22803A1 (en, 2012) |
| MD (1) | MD940047A (en, 2012) |
| MX (1) | MX9300855A (en, 2012) |
| NZ (1) | NZ245706A (en, 2012) |
| PL (1) | PL297750A1 (en, 2012) |
| RO (1) | RO108239B1 (en, 2012) |
| SI (1) | SI9300085A (en, 2012) |
| SK (1) | SK9593A3 (en, 2012) |
| TR (1) | TR26712A (en, 2012) |
| TW (1) | TW221369B (en, 2012) |
| ZA (1) | ZA93648B (en, 2012) |
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 |
| AU7935798A (en) * | 1997-07-01 | 1999-01-25 | Japan Association for Advancement of Phyto-Regulators, The | 3-(substituted phenyl)-4-halopyridazine derivatives, pesticides containi ng the same as the active ingredient, and intermediates thereof |
| 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 |
| US9212146B2 (en) | 2008-03-18 | 2015-12-15 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Substituted pyridazinones for the treatment of tumors |
| 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 TW TW082100534A patent/TW221369B/zh active
- 1993-01-29 ZA ZA93648A patent/ZA93648B/xx unknown
- 1993-02-04 EP EP93101695A patent/EP0556647A1/de not_active Withdrawn
- 1993-02-10 TR TR93/0138A patent/TR26712A/xx unknown
- 1993-02-12 CA CA002089451A patent/CA2089451A1/en not_active Abandoned
- 1993-02-12 AU AU33028/93A patent/AU647687B2/en not_active Ceased
- 1993-02-15 CZ CZ93196A patent/CZ19693A3/cs unknown
- 1993-02-15 RO RO93-00185A patent/RO108239B1/ro unknown
- 1993-02-15 BG BG97448A patent/BG97448A/xx unknown
- 1993-02-15 KR KR1019930002038A patent/KR930017878A/ko not_active Withdrawn
- 1993-02-16 JO JO19931744A patent/JO1744B1/en active
- 1993-02-16 HU HU9300425A patent/HUT64042A/hu unknown
- 1993-02-16 LV LV930121A patent/LV10152A/xx unknown
- 1993-02-16 SK SK9593A patent/SK9593A3/sk unknown
- 1993-02-16 JP JP5027000A patent/JPH069574A/ja not_active Withdrawn
- 1993-02-16 MA MA23096A patent/MA22803A1/fr unknown
- 1993-02-16 BR BR9300589A patent/BR9300589A/pt not_active Application Discontinuation
- 1993-02-16 HR HR930192A patent/HRP930192A2/hr not_active Application Discontinuation
- 1993-02-16 PL PL29775093A patent/PL297750A1/xx unknown
- 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 |
|---|---|
| BR9300589A (pt) | 1993-08-24 |
| HRP930192A2 (en) | 1995-12-31 |
| MD940047A (ro) | 1995-08-31 |
| HUT64042A (en) | 1993-11-29 |
| LV10152A (lv) | 1994-10-20 |
| EP0556647A1 (de) | 1993-08-25 |
| SK9593A3 (en) | 1993-09-09 |
| ATA25892A (de) | 1993-06-15 |
| MA22803A1 (fr) | 1993-10-01 |
| SI9300085A (en) | 1993-09-30 |
| IL104449A0 (en) | 1993-05-13 |
| BG97448A (en) | 1994-03-24 |
| AU647687B2 (en) | 1994-03-24 |
| CN1075477A (zh) | 1993-08-25 |
| US5462914A (en) | 1995-10-31 |
| RO108239B1 (ro) | 1994-03-31 |
| TW221369B (en, 2012) | 1994-03-01 |
| HU9300425D0 (en) | 1993-05-28 |
| MX9300855A (es) | 1993-08-01 |
| CZ19693A3 (en) | 1994-01-19 |
| AU3302893A (en) | 1993-08-19 |
| KR930017878A (ko) | 1993-09-20 |
| PL297750A1 (en) | 1993-11-02 |
| TR26712A (tr) | 1995-05-15 |
| NZ245706A (en) | 1994-11-25 |
| CA2089451A1 (en) | 1993-08-18 |
| JO1744B1 (en) | 1993-10-30 |
| JPH069574A (ja) | 1994-01-18 |
| EE9400149A (et) | 1995-12-15 |
| ZA93648B (en) | 1993-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EIH | Change in the person of patent owner | ||
| EFA | Change in the company name | ||
| ELJ | Ceased due to non-payment of the annual fee |