DK2955176T3 - Sammensætning indeholdende krystallinsk modifikation B af (3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-([5-(trifluormethyl)-2H-tetrazol-2-yl]methyl)-1H-pyrazol-5-carboxamid og anvendelse heraf - Google Patents
Sammensætning indeholdende krystallinsk modifikation B af (3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-([5-(trifluormethyl)-2H-tetrazol-2-yl]methyl)-1H-pyrazol-5-carboxamid og anvendelse heraf Download PDFInfo
- Publication number
- DK2955176T3 DK2955176T3 DK15171321.1T DK15171321T DK2955176T3 DK 2955176 T3 DK2955176 T3 DK 2955176T3 DK 15171321 T DK15171321 T DK 15171321T DK 2955176 T3 DK2955176 T3 DK 2955176T3
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- agrochemical composition
- chloropyridin
- trifluoromethyl
- pyrazole
- Prior art date
Links
- 238000012986 modification Methods 0.000 title claims 4
- 230000004048 modification Effects 0.000 title claims 4
- 239000000203 mixture Substances 0.000 title abstract description 50
- KNDVJPKNBVIKML-UHFFFAOYSA-N tetraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl KNDVJPKNBVIKML-UHFFFAOYSA-N 0.000 title description 3
- -1 tetrazole- substituted anthranilamide Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000004546 suspension concentrate Substances 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 13
- 239000012872 agrochemical composition Substances 0.000 claims description 11
- 239000000969 carrier Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 238000001237 Raman spectrum Methods 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 229910002483 Cu Ka Inorganic materials 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 241000238631 Hexapoda Species 0.000 claims 2
- 230000011514 reflex Effects 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 1
- 230000002528 anti-freeze Effects 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 22
- 239000013078 crystal Substances 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000004606 Fillers/Extenders Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- UNFSEYMJHZNPSB-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-5-[5-(trifluoromethyl)tetrazol-1-yl]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(N2C(=NN=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl UNFSEYMJHZNPSB-UHFFFAOYSA-N 0.000 description 3
- VRJIBCBHABNTRG-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-5-[[5-(trifluoromethyl)tetrazol-2-yl]methyl]pyrazole-3-carboxylic acid Chemical compound N=1N(C=2C(=CC=CN=2)Cl)C(C(=O)O)=CC=1CN1N=NC(C(F)(F)F)=N1 VRJIBCBHABNTRG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000002050 diffraction method Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- 239000012868 active agrochemical ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000008422 chlorobenzenes Chemical class 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 2
- 235000019838 diammonium phosphate Nutrition 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- RJTNIGNOVDQOAX-UHFFFAOYSA-N methyl 5-(chloromethyl)-2-(3-chloropyridin-2-yl)pyrazole-3-carboxylate Chemical compound COC(=O)C1=CC(CCl)=NN1C1=NC=CC=C1Cl RJTNIGNOVDQOAX-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000004477 pesticide formulation type Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- WMWSZMZGGPDYOW-UHFFFAOYSA-N sodium;5-(trifluoromethyl)-1,2,4-triaza-3-azanidacyclopenta-1,4-diene Chemical compound [Na+].FC(F)(F)C=1N=N[N-]N=1 WMWSZMZGGPDYOW-UHFFFAOYSA-N 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- WODZRMNEGCULTG-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-n-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-5-[5-(trifluoromethyl)tetrazol-1-yl]pyrazole-3-carboxamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(N2C(=NN=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl WODZRMNEGCULTG-UHFFFAOYSA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- UOCPQZOXOQZEGV-UHFFFAOYSA-N 2-amino-5-cyano-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1N UOCPQZOXOQZEGV-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical class OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- FOEPLOQMUWYHBM-UHFFFAOYSA-N 5-(trifluoromethyl)-2h-tetrazole Chemical compound FC(F)(F)C=1N=NNN=1 FOEPLOQMUWYHBM-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 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
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron 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
- 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
- 239000000084 colloidal system Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229910052802 copper 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
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 235000009973 maize Nutrition 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
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- KMACQTVWJGBLLR-UHFFFAOYSA-N methyl 5-(3-chloropyridin-2-yl)-3-[[5-(trifluoromethyl)-1,3-dihydrotetrazol-2-yl]methyl]cyclopenta-1,3-diene-1-carboxylate Chemical compound C=1C(C=2C(=CC=CN=2)Cl)C(C(=O)OC)=CC=1CN1NN=C(C(F)(F)F)N1 KMACQTVWJGBLLR-UHFFFAOYSA-N 0.000 description 1
- FOAKTTDOHAEVQN-UHFFFAOYSA-N methyl 5-(3-chloropyridin-2-yl)-3-[[5-(trifluoromethyl)tetrazol-2-yl]methyl]cyclopenta-1,3-diene-1-carboxylate Chemical compound C=1C(C=2C(=CC=CN=2)Cl)C(C(=O)OC)=CC=1CN1N=NC(C(F)(F)F)=N1 FOAKTTDOHAEVQN-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Catching Or Destruction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (6)
1. Agrokemisk sammensætning omfattende den krystallinske modifikation B af forbindelsen med formel (I—1)
kendetegnet ved, at den røntgen-pulverdiffraktogram ved anvendelse af Cu Κα-stråling har i det mindste følgende reflekspositioner:
idet den agrokemiske sammensætning endvidere indeholder i det mindste et hjælpestof udvalgt af strækmidler, opløsningsmidler og/eller faste bærestoffer og/eller overfladeaktive stoffer.
2. Agrokemisk sammensætning ifølge krav 1, kendetegnet ved, at røntgen-pulverdiffraktogrammet af den krystallinske modifikation B i forbindelsen (I — 1) ved anvendelse af Cu Ka-stråling har i det mindste følgende yderligere reflekspositioner:
3. Agrokemisk sammensætning ifølge et af kravene 1-2, kendetegnet ved, at Raman-spektrummet af den krystallinske modifikation B i forbindelsen med formel (I — 1) har i det mindste følaende bander:
4. Agrokemisk sammensætning ifølge et af kravene 1-3 omfattende et eller flere hjælpestoffer udvalgt af strækmidler, opløsningsmidler, spontanitetsfremmende midler, bærestoffer, emulgeringsmidler, dispergeringsmidler, frostbeskyttelsesmidler, biocider, fortykningsmidler og/eller adj uvanser.
5. Agrokemisk sammensætning ifølge et af kravene 1-4, kendetegnet ved, at det drejer sig om et suspensionskoncentrat.
6. Fremgangsmåde til bekæmpelse af uønskede insekter, kendetegnet ved, at en agrokemisk sammensætning ifølge et af kravene 1-5 udbringes på insekterne og/eller deres levesteder og/eller såsæd, undtagen til terapeutisk behandling af det animalske eller menneskelige legeme.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35492010P | 2010-06-15 | 2010-06-15 | |
| EP10166059 | 2010-06-15 | ||
| EP11726391.3A EP2582694B1 (de) | 2010-06-15 | 2011-06-10 | Verfahren zur herstellung von tetrazol-substituierten anthranilsäurediamid-derivaten und neue kristalline modifikation dieser derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2955176T3 true DK2955176T3 (da) | 2018-03-12 |
Family
ID=42989671
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK15171321.1T DK2955176T3 (da) | 2010-06-15 | 2011-06-10 | Sammensætning indeholdende krystallinsk modifikation B af (3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-([5-(trifluormethyl)-2H-tetrazol-2-yl]methyl)-1H-pyrazol-5-carboxamid og anvendelse heraf |
| DK11726391.3T DK2582694T3 (da) | 2010-06-15 | 2011-06-10 | Fremgangsmåde til fremstilling af tetrazol-substituerede anthranilsyrediamidderivater og ny krystallinsk modifikation af disse derivater |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK11726391.3T DK2582694T3 (da) | 2010-06-15 | 2011-06-10 | Fremgangsmåde til fremstilling af tetrazol-substituerede anthranilsyrediamidderivater og ny krystallinsk modifikation af disse derivater |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US8969572B2 (da) |
| EP (2) | EP2955176B1 (da) |
| JP (3) | JP6199739B2 (da) |
| KR (1) | KR101790305B1 (da) |
| CN (1) | CN103261187B (da) |
| BR (1) | BR112012032244A2 (da) |
| DK (2) | DK2955176T3 (da) |
| ES (2) | ES2547314T3 (da) |
| HR (1) | HRP20151088T1 (da) |
| HU (1) | HUE027943T2 (da) |
| MX (2) | MX347841B (da) |
| PL (1) | PL2582694T3 (da) |
| PT (1) | PT2582694E (da) |
| RS (1) | RS54277B1 (da) |
| SI (1) | SI2582694T1 (da) |
| TW (1) | TWI511668B (da) |
| WO (1) | WO2011157664A1 (da) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6199739B2 (ja) * | 2010-06-15 | 2017-09-20 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | テトラゾール置換されたアントラニルアミド誘導体およびこれら誘導体の新規な結晶多形体の製造方法 |
| MX341267B (es) * | 2010-06-18 | 2016-08-09 | Bayer Ip Gmbh | Combinaciones de principios activos con propiedades insecticidas y acaricidas. |
| UA111593C2 (uk) * | 2010-07-07 | 2016-05-25 | Баєр Інтеллекчуел Проперті Гмбх | Аміди антранілової кислоти у комбінації з фунгіцидами |
| KR20130093086A (ko) * | 2010-07-09 | 2013-08-21 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 농약으로서의 안트라닐산 디아미드 유도체 |
| JP2015511229A (ja) * | 2012-02-07 | 2015-04-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換アントラニル酸誘導体を製造する方法 |
| EP2649879A1 (en) | 2012-04-10 | 2013-10-16 | Basf Se | Pesticidal mixtures containing fluxapyroxad |
| WO2013156331A1 (en) | 2012-04-16 | 2013-10-24 | Basf Se | Synergistic compositions comprising pyraclostrobin and an insecticidal compound |
| JP6321042B2 (ja) * | 2013-02-06 | 2018-05-09 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規なハロゲン置換された化合物 |
| CN108697088A (zh) | 2016-02-19 | 2018-10-23 | 巴斯夫欧洲公司 | 包含邻氨基苯甲酰胺类化合物的农药活性混合物 |
| TWI696615B (zh) * | 2016-05-05 | 2020-06-21 | 瑞士商伊蘭科動物健康公司 | 雜芳基-1,2,4-三唑及雜芳基-三唑化合物 |
| US12024510B2 (en) | 2017-12-20 | 2024-07-02 | Pi Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same |
| WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
| US12221436B2 (en) | 2018-01-30 | 2025-02-11 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same |
| CN112119071B (zh) * | 2018-05-21 | 2024-08-02 | Pi工业有限公司 | 制备邻甲酰氨基苯甲酰胺类化合物的方法 |
| IL279890B2 (en) | 2018-07-20 | 2024-02-01 | Pi Industries Ltd | A process for the preparation of enteric diamides |
| HUE069962T2 (hu) | 2019-02-18 | 2025-04-28 | Pi Industries Ltd | Eljárás antranil-diamidok és intermedierjeik elõállítására |
| KR102841700B1 (ko) | 2019-02-22 | 2025-08-01 | 피아이 인더스트리스 엘티디. | 안트라닐산 디아미드 화합물 및 그의 중간체의 합성 방법 |
| TWI878337B (zh) * | 2019-08-19 | 2025-04-01 | 美商富曼西公司 | 用於製備3-鹵代-4,5-二氫-1h-吡唑的羧酸衍生物的方法 |
| EP3964506A1 (de) * | 2020-09-04 | 2022-03-09 | Bayer Aktiengesellschaft | Verfahren zur herstellung eines tetrazol-substituierten anthranilsäurediamid-derivates |
| WO2022058916A1 (en) | 2020-09-17 | 2022-03-24 | Pi Industries Limited | A process for the synthesis of anthranilic acid/amide compounds and intermediates thereof |
| AR123593A1 (es) | 2020-09-26 | 2022-12-21 | Pi Industries Ltd | Un proceso para la síntesis de compuestos antranílicos de ácido / amida e intermedios de los mismos |
| JP2024528002A (ja) | 2021-07-27 | 2024-07-26 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | ジアミド耐性有害生物の防除のための方法及びそのための化合物 |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| MX2024002008A (es) | 2021-08-19 | 2024-03-05 | Syngenta Crop Protection Ag | Metodo para controlar plagas resistentes a diamidas y compuestos para el mismo. |
| WO2023110710A1 (en) | 2021-12-13 | 2023-06-22 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| EP4197333A1 (en) | 2021-12-15 | 2023-06-21 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
| WO2024133426A1 (en) | 2022-12-21 | 2024-06-27 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests and compounds therefor |
| PY24113048A (es) | 2023-12-19 | 2025-10-10 | Pi Industries Ltd | Un metodo para la sintesis de compuestos de amidas antranilicas sustituidas, intermediarios y sales de los mismos |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR043048A1 (es) | 2002-08-30 | 2005-07-13 | Syngenta Participations Ag | Derivados de 4-(3,3-dihalo- aliloxi) fenol con propiedades pesticidas |
| CA2536253A1 (en) * | 2003-08-20 | 2005-03-03 | Vertex Pharmaceuticals Incorporated | Aminofurazan compounds useful as protein kinase inhibitors |
| WO2006023783A1 (en) | 2004-08-17 | 2006-03-02 | E.I. Dupont De Nemours And Company | Novel anthranilamides useful for controlling invertebrate pests |
| CN101466702B (zh) * | 2006-06-13 | 2014-04-02 | 拜尔农作物科学股份公司 | 具有杂芳族和杂环族取代基的邻氨基苯甲酰二胺衍生物 |
| DE102006032168A1 (de) * | 2006-06-13 | 2007-12-20 | Bayer Cropscience Ag | Anthranilsäurediamid-Derivate mit heteroaromatischen Substituenten |
| KR101687743B1 (ko) * | 2008-12-18 | 2016-12-19 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 살해충제로서의 테트라졸 치환된 안트라닐산 아미드 |
| JP6199739B2 (ja) * | 2010-06-15 | 2017-09-20 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | テトラゾール置換されたアントラニルアミド誘導体およびこれら誘導体の新規な結晶多形体の製造方法 |
-
2011
- 2011-06-10 JP JP2013514665A patent/JP6199739B2/ja active Active
- 2011-06-10 EP EP15171321.1A patent/EP2955176B1/de active Active
- 2011-06-10 HR HRP20151088TT patent/HRP20151088T1/hr unknown
- 2011-06-10 PT PT117263913T patent/PT2582694E/pt unknown
- 2011-06-10 ES ES11726391.3T patent/ES2547314T3/es active Active
- 2011-06-10 MX MX2015009721A patent/MX347841B/es unknown
- 2011-06-10 KR KR1020137000731A patent/KR101790305B1/ko active Active
- 2011-06-10 PL PL11726391T patent/PL2582694T3/pl unknown
- 2011-06-10 RS RS20150651A patent/RS54277B1/sr unknown
- 2011-06-10 DK DK15171321.1T patent/DK2955176T3/da active
- 2011-06-10 HU HUE11726391A patent/HUE027943T2/en unknown
- 2011-06-10 CN CN201180039525.0A patent/CN103261187B/zh active Active
- 2011-06-10 DK DK11726391.3T patent/DK2582694T3/da active
- 2011-06-10 BR BR112012032244A patent/BR112012032244A2/pt not_active Application Discontinuation
- 2011-06-10 WO PCT/EP2011/059735 patent/WO2011157664A1/de not_active Ceased
- 2011-06-10 SI SI201130627T patent/SI2582694T1/sl unknown
- 2011-06-10 ES ES15171321.1T patent/ES2660305T3/es active Active
- 2011-06-10 EP EP11726391.3A patent/EP2582694B1/de active Active
- 2011-06-10 MX MX2012014775A patent/MX2012014775A/es active IP Right Grant
- 2011-06-14 TW TW100120623A patent/TWI511668B/zh active
- 2011-06-14 US US13/159,961 patent/US8969572B2/en active Active
-
2014
- 2014-09-22 US US14/492,264 patent/US9056861B2/en active Active
-
2015
- 2015-11-11 JP JP2015221282A patent/JP6170118B2/ja active Active
-
2016
- 2016-07-20 JP JP2016142220A patent/JP6254646B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20151088T1 (hr) | 2015-11-20 |
| US20120101133A1 (en) | 2012-04-26 |
| CN103261187B (zh) | 2016-08-03 |
| US20150025116A1 (en) | 2015-01-22 |
| KR101790305B1 (ko) | 2017-10-25 |
| TWI511668B (zh) | 2015-12-11 |
| EP2955176B1 (de) | 2017-12-06 |
| US8969572B2 (en) | 2015-03-03 |
| JP2017008062A (ja) | 2017-01-12 |
| MX2012014775A (es) | 2013-01-29 |
| JP6199739B2 (ja) | 2017-09-20 |
| WO2011157664A1 (de) | 2011-12-22 |
| BR112012032244A2 (pt) | 2016-09-27 |
| TW201212820A (en) | 2012-04-01 |
| MX347841B (es) | 2017-05-16 |
| PL2582694T3 (pl) | 2015-12-31 |
| PT2582694E (pt) | 2015-10-15 |
| JP6170118B2 (ja) | 2017-07-26 |
| EP2582694B1 (de) | 2015-07-22 |
| CN103261187A (zh) | 2013-08-21 |
| JP2016065076A (ja) | 2016-04-28 |
| ES2660305T3 (es) | 2018-03-21 |
| RS54277B1 (sr) | 2016-02-29 |
| EP2955176A1 (de) | 2015-12-16 |
| HUE027943T2 (en) | 2016-11-28 |
| DK2582694T3 (da) | 2015-10-26 |
| SI2582694T1 (sl) | 2015-11-30 |
| US9056861B2 (en) | 2015-06-16 |
| JP2013530175A (ja) | 2013-07-25 |
| ES2547314T3 (es) | 2015-10-05 |
| JP6254646B2 (ja) | 2017-12-27 |
| KR20130112860A (ko) | 2013-10-14 |
| EP2582694A1 (de) | 2013-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2582694T3 (da) | Fremgangsmåde til fremstilling af tetrazol-substituerede anthranilsyrediamidderivater og ny krystallinsk modifikation af disse derivater | |
| CN110950810B (zh) | 三氮唑化合物及其在农业中的应用 | |
| AU655014B2 (en) | Pesticidal 1-aryl-5-(substituted alkylideneimino)-pyrazoles | |
| JPH10502661A (ja) | ３−フェニルピラゾール誘導体をベースとする植物繁殖材料の処理用殺菌組成物、新規３−フェニルピラゾール誘導体及びその殺菌利用 | |
| JPH08502736A (ja) | 除草性ピコリンアミド誘導体 | |
| CN108349899B (zh) | 卤代喹那菌素的衍生物 | |
| EP3826991A1 (en) | Crystalline form of fluopyram | |
| CN114478506B (zh) | 吡啶噁唑类化合物及其应用 | |
| JPS59176288A (ja) | 新規な２−シアノイミダゾピリジン誘導体、その製造方法および殺菌剤としてのその使用 | |
| CN113429356A (zh) | 三唑磺酰胺类衍生物及其在农业中应用 | |
| CN114437056A (zh) | 吡啶噁二唑酮类化合物及其应用 | |
| CN114163400B (zh) | 环己二酮-苯并噻二嗪类化合物及其应用 | |
| JP2001518106A (ja) | １，３−ジ置換２−ニトログアニジンの製造法 | |
| CN114507226B (zh) | 含氯氟取代基的吡啶噁唑类化合物及其应用 | |
| DD252114A5 (de) | Herbizide mittel | |
| CN121717800A (zh) | 一种吡唑类化合物及其制备方法和应用 | |
| CN112442018A (zh) | 三唑-1,3-二磺酰胺衍生物及其在农业中的应用 | |
| CN114507226A (zh) | 含氯氟取代基的吡啶噁唑类化合物及其应用 | |
| CN113929665A (zh) | 芳香基取代的三唑磺酰胺衍生物及其制备方法和应用 | |
| SK46796A3 (en) | N-pyridinyl£1,2,4|triazolo£1,5-c|pyrimidine-2-sulfonamide compound, herbicidal agent containing this compound and a regulation method of undesirable vegetation | |
| DE3605343A1 (de) | Imidazolinyl-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel mit herbizider wirkung |