DD244550A5 - Alkanoylaniliden - Google Patents
Alkanoylaniliden Download PDFInfo
- Publication number
- DD244550A5 DD244550A5 DD86288741A DD28874186A DD244550A5 DD 244550 A5 DD244550 A5 DD 244550A5 DD 86288741 A DD86288741 A DD 86288741A DD 28874186 A DD28874186 A DD 28874186A DD 244550 A5 DD244550 A5 DD 244550A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- nitro
- group
- trifluoromethyl
- tetrafluoro
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- -1 perfluoropiperidino Chemical group 0.000 claims description 47
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000003863 ammonium salts Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 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 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 111
- CPOGGUYXOJBWHC-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical group [O-][N+](=O)C1=CC=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(Br)=C1 CPOGGUYXOJBWHC-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 9
- 230000000749 insecticidal effect Effects 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 54
- 239000000203 mixture Substances 0.000 description 46
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- 239000004480 active ingredient Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000004927 clay Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 241000239223 Arachnida Species 0.000 description 10
- 240000008042 Zea mays Species 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 241000239290 Araneae Species 0.000 description 7
- 231100000674 Phytotoxicity Toxicity 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 6
- 241000282320 Panthera leo Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 241000255967 Helicoverpa zea Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 3
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 3
- 241001558864 Aceria Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000449794 Alabama argillacea Species 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241000257303 Hymenoptera Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- 241000496694 Vasates Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 241001136249 Agriotes lineatus Species 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241000987201 Brevipalpus californicus Species 0.000 description 2
- 241001055897 Bryobia rubrioculus Species 0.000 description 2
- 241001425384 Cacopsylla pyricola Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000068645 Carya illinoensis Species 0.000 description 2
- 235000009025 Carya illinoensis Nutrition 0.000 description 2
- 241001221118 Cecidophyopsis ribis Species 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000255942 Choristoneura fumiferana Species 0.000 description 2
- 241000931705 Cicada Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241001635274 Cydia pomonella Species 0.000 description 2
- 241000489975 Diabrotica Species 0.000 description 2
- 241000586568 Diaspidiotus perniciosus Species 0.000 description 2
- 241001515281 Eotetranychus lewisi Species 0.000 description 2
- 241000627753 Eriophyes padi Species 0.000 description 2
- 241001619920 Euschistus servus Species 0.000 description 2
- 241000851181 Eutetranychus orientalis Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 241001441330 Grapholita molesta Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000358422 Nephotettix cincticeps Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241001147398 Ostrinia nubilalis Species 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000907661 Pieris rapae Species 0.000 description 2
- 241000691880 Planococcus citri Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 2
- 241001617044 Rhizoglyphus Species 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000736128 Solenopsis invicta Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001265 acyl fluorides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000000415 inactivating effect Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- KMOQTEVNEQPBJM-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(1,1,2,2,2-pentafluoroethoxy)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(OC(F)(F)C(F)(F)F)C(F)(F)F)C(Br)=C1 KMOQTEVNEQPBJM-UHFFFAOYSA-N 0.000 description 2
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 1
- YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 1
- BRWSHOSLZPMKII-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)C(F)(F)F BRWSHOSLZPMKII-UHFFFAOYSA-N 0.000 description 1
- GIYRQQVGUJGTBO-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-n-(2,3,4,5,6-pentafluorophenyl)-2-(trifluoromethyl)propanamide Chemical compound FC1=C(F)C(F)=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(F)=C1F GIYRQQVGUJGTBO-UHFFFAOYSA-N 0.000 description 1
- IIJSXEBEHPVKJK-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-n-(2,3,4,5-tetrachlorophenyl)-2-(trifluoromethyl)propanamide Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(=O)NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl IIJSXEBEHPVKJK-UHFFFAOYSA-N 0.000 description 1
- OUCBVMGBXZNBHL-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-n-(2,3,4,6-tetrafluorophenyl)-2-(trifluoromethyl)propanamide Chemical compound FC1=CC(F)=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(F)=C1F OUCBVMGBXZNBHL-UHFFFAOYSA-N 0.000 description 1
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- IRACAAYNHBSMSC-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(Br)=C1 IRACAAYNHBSMSC-UHFFFAOYSA-N 0.000 description 1
- VIPZUISFWDOFLZ-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,4,4,4-nonafluorobutoxy)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(Br)=C1 VIPZUISFWDOFLZ-UHFFFAOYSA-N 0.000 description 1
- KIMIHKXTZIDQEE-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(2,2,3,3,5,5,6,6-octafluoromorpholin-4-yl)propanamide Chemical compound BrC1=CC([N+](=O)[O-])=CC=C1NC(=O)C(F)(C(F)(F)F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F KIMIHKXTZIDQEE-UHFFFAOYSA-N 0.000 description 1
- SPJPNBCKQKYPAY-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,3-tetrafluoro-n-methyl-2-(trifluoromethyl)propanamide Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(=O)N(C)C1=CC=C([N+]([O-])=O)C=C1Br SPJPNBCKQKYPAY-UHFFFAOYSA-N 0.000 description 1
- PVNLMNJONPCAHT-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-2,3,3,4,4,5,5,5-octafluoro-2-(trifluoromethyl)pentanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F)C(Br)=C1 PVNLMNJONPCAHT-UHFFFAOYSA-N 0.000 description 1
- MYQKYJUSUPJDTB-UHFFFAOYSA-N n-(2-bromo-6-cyano-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound [O-][N+](=O)C1=CC(Br)=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(C#N)=C1 MYQKYJUSUPJDTB-UHFFFAOYSA-N 0.000 description 1
- LZCGILGNQQNYFJ-UHFFFAOYSA-N n-(2-chloro-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(Cl)=C1 LZCGILGNQQNYFJ-UHFFFAOYSA-N 0.000 description 1
- GYDMXRBTVXAJQY-UHFFFAOYSA-N n-(2-chloro-5-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)=C1 GYDMXRBTVXAJQY-UHFFFAOYSA-N 0.000 description 1
- QSAIZZBLKUBKCG-UHFFFAOYSA-N n-(2-cyano-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(C#N)=C1 QSAIZZBLKUBKCG-UHFFFAOYSA-N 0.000 description 1
- RPEXYCMKOHSRMV-UHFFFAOYSA-N n-(2-cyano-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(C#N)=C1 RPEXYCMKOHSRMV-UHFFFAOYSA-N 0.000 description 1
- TVOGPGLULKOCCX-UHFFFAOYSA-N n-(3-chloro-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C(F)(C(F)(F)F)C(F)(F)F)C=C1Cl TVOGPGLULKOCCX-UHFFFAOYSA-N 0.000 description 1
- IYADOQXJAFSBOD-UHFFFAOYSA-N n-(4-chloro-2-cyanophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(=O)NC1=CC=C(Cl)C=C1C#N IYADOQXJAFSBOD-UHFFFAOYSA-N 0.000 description 1
- VPYKBFKSFPAHOA-UHFFFAOYSA-N n-(5-chloro-2-methyl-4-nitrophenyl)-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound CC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(=O)C(F)(C(F)(F)F)C(F)(F)F VPYKBFKSFPAHOA-UHFFFAOYSA-N 0.000 description 1
- WMUVUQOHPOAXJQ-UHFFFAOYSA-N n-[4-bromo-2-(trifluoromethyl)phenyl]-2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanamide Chemical compound FC(F)(F)C1=CC(Br)=CC=C1NC(=O)C(F)(C(F)(F)F)C(F)(F)F WMUVUQOHPOAXJQ-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000008653 root damage Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- FLXZVVQJJIGXRS-UHFFFAOYSA-N trimethyl(octadecyl)azanium hydrate Chemical compound O.CCCCCCCCCCCCCCCCCC[N+](C)(C)C FLXZVVQJJIGXRS-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72023685A | 1985-04-05 | 1985-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD244550A5 true DD244550A5 (de) | 1987-04-08 |
Family
ID=24893209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86288741A DD244550A5 (de) | 1985-04-05 | 1986-04-03 | Alkanoylaniliden |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0197756A3 (pt) |
| JP (1) | JPS61236755A (pt) |
| KR (1) | KR900006518B1 (pt) |
| CN (1) | CN1012575B (pt) |
| AU (1) | AU588297B2 (pt) |
| BG (1) | BG46743A3 (pt) |
| BR (1) | BR8601567A (pt) |
| DD (1) | DD244550A5 (pt) |
| DK (1) | DK154586A (pt) |
| ES (1) | ES8707921A1 (pt) |
| GR (1) | GR860893B (pt) |
| HU (1) | HU198606B (pt) |
| IL (1) | IL78394A (pt) |
| NZ (1) | NZ215673A (pt) |
| PH (1) | PH23012A (pt) |
| PL (1) | PL146891B1 (pt) |
| PT (1) | PT82323B (pt) |
| SU (1) | SU1528343A3 (pt) |
| ZA (1) | ZA862474B (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL78392A (en) * | 1985-04-05 | 1989-08-15 | Lilly Co Eli | Insecticidal compositions for inhibiting diabrotica larvae,comprising fluorinated cyclopentane(or hexane)carboxanilides |
| US4962284A (en) * | 1985-04-05 | 1990-10-09 | Eli Lilly And Company | Alkanoyl anilides |
| US4826841A (en) * | 1985-04-05 | 1989-05-02 | Eli Lilly And Company | Alkanoyl anilides as pesticides |
| GB8607033D0 (en) * | 1986-03-21 | 1986-04-30 | Lilly Industries Ltd | Molluscicides |
| IE62559B1 (en) * | 1989-02-02 | 1995-02-08 | Ici Plc | Fungicides |
| CN113292443B (zh) * | 2020-11-24 | 2022-07-19 | 长沙理工大学 | 酰胺的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113967A (en) * | 1960-10-25 | 1963-12-10 | Du Pont | Addition of carbonyl fluoride to polyfluoro-olefins |
| DE2042300A1 (de) * | 1970-08-26 | 1972-03-23 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Halogencarbonsäureanilide, ihre Herstellung und Verwendung als Herbizide |
| US3839446A (en) * | 1970-11-18 | 1974-10-01 | Stauffer Chemical Co | Ether and sulfide meta-substituted anilides |
-
1986
- 1986-03-31 IL IL78394A patent/IL78394A/xx unknown
- 1986-04-01 AU AU55527/86A patent/AU588297B2/en not_active Ceased
- 1986-04-02 EP EP86302435A patent/EP0197756A3/en not_active Withdrawn
- 1986-04-02 PT PT82323A patent/PT82323B/pt not_active IP Right Cessation
- 1986-04-02 NZ NZ215673A patent/NZ215673A/xx unknown
- 1986-04-02 PH PH33615A patent/PH23012A/en unknown
- 1986-04-03 CN CN86102262A patent/CN1012575B/zh not_active Expired
- 1986-04-03 ZA ZA862474A patent/ZA862474B/xx unknown
- 1986-04-03 GR GR860893A patent/GR860893B/el unknown
- 1986-04-03 HU HU861413A patent/HU198606B/hu not_active IP Right Cessation
- 1986-04-03 DD DD86288741A patent/DD244550A5/de not_active IP Right Cessation
- 1986-04-03 BG BG074402A patent/BG46743A3/xx unknown
- 1986-04-03 ES ES553705A patent/ES8707921A1/es not_active Expired
- 1986-04-04 JP JP61079062A patent/JPS61236755A/ja active Pending
- 1986-04-04 DK DK154586A patent/DK154586A/da not_active Application Discontinuation
- 1986-04-04 SU SU864027304A patent/SU1528343A3/ru active
- 1986-04-04 BR BR8601567A patent/BR8601567A/pt unknown
- 1986-04-04 PL PL1986258778A patent/PL146891B1/pl unknown
- 1986-04-04 KR KR1019860002563A patent/KR900006518B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CN86102262A (zh) | 1986-11-19 |
| SU1528343A3 (ru) | 1989-12-07 |
| DK154586D0 (da) | 1986-04-04 |
| PT82323B (pt) | 1988-10-14 |
| EP0197756A3 (en) | 1988-08-24 |
| EP0197756A2 (en) | 1986-10-15 |
| IL78394A0 (en) | 1986-07-31 |
| BR8601567A (pt) | 1986-12-09 |
| NZ215673A (en) | 1989-02-24 |
| AU588297B2 (en) | 1989-09-14 |
| DK154586A (da) | 1986-10-06 |
| HUT42679A (en) | 1987-08-28 |
| PH23012A (en) | 1989-03-03 |
| PT82323A (en) | 1986-05-01 |
| KR860008124A (ko) | 1986-11-12 |
| PL146891B1 (en) | 1989-03-31 |
| ES8707921A1 (es) | 1987-09-01 |
| JPS61236755A (ja) | 1986-10-22 |
| GR860893B (en) | 1986-07-29 |
| BG46743A3 (en) | 1990-02-15 |
| CN1012575B (zh) | 1991-05-08 |
| IL78394A (en) | 1989-12-15 |
| KR900006518B1 (ko) | 1990-09-03 |
| HU198606B (en) | 1989-11-28 |
| ES553705A0 (es) | 1987-09-01 |
| AU5552786A (en) | 1986-10-09 |
| ZA862474B (en) | 1987-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |