CH542578A - Herbicides Mittel - Google Patents
Herbicides MittelInfo
- Publication number
- CH542578A CH542578A CH407971A CH407971A CH542578A CH 542578 A CH542578 A CH 542578A CH 407971 A CH407971 A CH 407971A CH 407971 A CH407971 A CH 407971A CH 542578 A CH542578 A CH 542578A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- pyridine
- imidazo
- trifluoromethyl
- chloro
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 16
- -1 tetrahydro-2-pyranyl Chemical group 0.000 claims description 52
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- LMNUMNZYWMPDPX-UHFFFAOYSA-N 1-hydroxy-2,6-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1=C(C(F)(F)F)C=C2N(O)C(C(F)(F)F)=NC2=N1 LMNUMNZYWMPDPX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- QPMKMQSDFKLKKE-UHFFFAOYSA-N 6-chloro-1-methoxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical group C1=C(Cl)C=C2N(OC)C(C(F)(F)F)=NC2=N1 QPMKMQSDFKLKKE-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- RVAUFHAJSOMPOZ-UHFFFAOYSA-N NCl[N+]([O-])=O Chemical group NCl[N+]([O-])=O RVAUFHAJSOMPOZ-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- NOZGDEXIPWYTQS-UHFFFAOYSA-N 1-methoxy-2,6-bis(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1=C(C(F)(F)F)C=C2N(OC)C(C(F)(F)F)=NC2=N1 NOZGDEXIPWYTQS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 71
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 28
- 239000004480 active ingredient Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 230000006378 damage Effects 0.000 description 18
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 240000008042 Zea mays Species 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 244000025254 Cannabis sativa Species 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XLWYJKNUQDXZNS-UHFFFAOYSA-N 6-chloro-1-hydroxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound C1=C(Cl)C=C2N(O)C(C(F)(F)F)=NC2=N1 XLWYJKNUQDXZNS-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 8
- 235000009973 maize Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- GILTXHIJUUIMPI-UHFFFAOYSA-N 5-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC=C(Cl)C=C1[N+]([O-])=O GILTXHIJUUIMPI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- KPBVULMMLSWXRR-UHFFFAOYSA-N 5-methylsulfonyl-3-nitropyridin-2-amine Chemical compound CS(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 KPBVULMMLSWXRR-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 240000000982 Malva neglecta Species 0.000 description 5
- 235000000060 Malva neglecta Nutrition 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000002440 hydroxy compounds Chemical class 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LHUVKANNSWTRJI-UHFFFAOYSA-N 3-nitro-5-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=NC=C(C(F)(F)F)C=C1[N+]([O-])=O LHUVKANNSWTRJI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- AHFINSWGYAZBOZ-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)benzaldehyde Chemical group FC(F)(F)C1=CC(Cl)=CC=C1C=O AHFINSWGYAZBOZ-UHFFFAOYSA-N 0.000 description 3
- SAVHMVDMLIZZMR-UHFFFAOYSA-N 5-ethylsulfonyl-3-nitropyridin-2-amine Chemical compound CCS(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 SAVHMVDMLIZZMR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000009422 growth inhibiting effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QLCLLKCOKMEPIR-UHFFFAOYSA-N n-(5-chloro-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide Chemical compound [O-][N+](=O)C1=CC(Cl)=CN=C1NC(=O)C(F)(F)F QLCLLKCOKMEPIR-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- IYXUFOCLMOXQSL-UHFFFAOYSA-N (2,2-difluoroacetyl) 2,2-difluoroacetate Chemical compound FC(F)C(=O)OC(=O)C(F)F IYXUFOCLMOXQSL-UHFFFAOYSA-N 0.000 description 2
- ZPONMSNSHOKRCY-UHFFFAOYSA-N 1-hydroxyimidazo[4,5-b]pyridine Chemical compound C1=CC=C2N(O)C=NC2=N1 ZPONMSNSHOKRCY-UHFFFAOYSA-N 0.000 description 2
- VNHUIEZQCNKMHC-UHFFFAOYSA-N 2,2,2-trifluoro-n-(5-methylsulfonyl-3-nitropyridin-2-yl)acetamide Chemical compound CS(=O)(=O)C1=CN=C(NC(=O)C(F)(F)F)C([N+]([O-])=O)=C1 VNHUIEZQCNKMHC-UHFFFAOYSA-N 0.000 description 2
- ZAXVRQSOOBYIDF-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-nitro-5-(trifluoromethyl)pyridin-2-yl]acetamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CN=C1NC(=O)C(F)(F)F ZAXVRQSOOBYIDF-UHFFFAOYSA-N 0.000 description 2
- IBERRFNKHKGPTO-UHFFFAOYSA-N 2-(difluoromethyl)-1-hydroxy-6-nitroimidazo[4,5-b]pyridine Chemical compound C1=C([N+]([O-])=O)C=C2N(O)C(C(F)F)=NC2=N1 IBERRFNKHKGPTO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ATOSRMNVMSTERR-UHFFFAOYSA-N 5-butylsulfonyl-3-nitropyridin-2-amine Chemical compound CCCCS(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 ATOSRMNVMSTERR-UHFFFAOYSA-N 0.000 description 2
- APJDHTWUGLVNAG-UHFFFAOYSA-N 5-methylsulfanyl-2-nitropyridine Chemical compound CSC1=CC=C([N+]([O-])=O)N=C1 APJDHTWUGLVNAG-UHFFFAOYSA-N 0.000 description 2
- IITUTZAGIVPTQC-UHFFFAOYSA-N 5-methylsulfonyl-2-nitropyridine Chemical compound CS(=O)(=O)C1=CC=C([N+]([O-])=O)N=C1 IITUTZAGIVPTQC-UHFFFAOYSA-N 0.000 description 2
- YDVCUSJBYYFJPM-UHFFFAOYSA-N 5-methylsulfonylpyridin-2-amine Chemical compound CS(=O)(=O)C1=CC=C(N)N=C1 YDVCUSJBYYFJPM-UHFFFAOYSA-N 0.000 description 2
- BQAVWUXSDWWPJX-UHFFFAOYSA-N 5-tert-butylsulfonyl-3-nitropyridin-2-amine Chemical compound CC(C)(C)S(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 BQAVWUXSDWWPJX-UHFFFAOYSA-N 0.000 description 2
- QLCAGLSZKLRPHZ-UHFFFAOYSA-N 6-butylsulfonyl-1-hydroxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound CCCCS(=O)(=O)C1=CN=C2N=C(C(F)(F)F)N(O)C2=C1 QLCAGLSZKLRPHZ-UHFFFAOYSA-N 0.000 description 2
- FWYNKHLQNXGRDY-UHFFFAOYSA-N 6-chloro-1-hydroxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine;n,n-diethylethanamine Chemical compound CCN(CC)CC.C1=C(Cl)C=C2N(O)C(C(F)(F)F)=NC2=N1 FWYNKHLQNXGRDY-UHFFFAOYSA-N 0.000 description 2
- KNXVBWHBZKRLEL-UHFFFAOYSA-N 6-chloro-1-hydroxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine;phenylmethanamine Chemical compound NCC1=CC=CC=C1.C1=C(Cl)C=C2N(O)C(C(F)(F)F)=NC2=N1 KNXVBWHBZKRLEL-UHFFFAOYSA-N 0.000 description 2
- ZAGJBMOYOPDVCQ-UHFFFAOYSA-N 6-chloro-1-phenylmethoxy-2-(trifluoromethyl)imidazo[4,5-b]pyridine Chemical compound FC(F)(F)C1=NC2=NC=C(Cl)C=C2N1OCC1=CC=CC=C1 ZAGJBMOYOPDVCQ-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YOHNVHFYTCNVHH-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] acetate Chemical compound C1=C(Cl)C=C2N(OC(=O)C)C(C(F)(F)F)=NC2=N1 YOHNVHFYTCNVHH-UHFFFAOYSA-N 0.000 description 2
- ZSNBVFICQYXDMM-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] methanesulfonate Chemical compound C1=C(Cl)C=C2N(OS(=O)(=O)C)C(C(F)(F)F)=NC2=N1 ZSNBVFICQYXDMM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
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- NUUJHDKRHOIWRJ-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] 2-phenylacetate Chemical compound FC(F)(F)C1=NC2=NC=C(Cl)C=C2N1OC(=O)CC1=CC=CC=C1 NUUJHDKRHOIWRJ-UHFFFAOYSA-N 0.000 description 1
- FYUQTKJEXWZHFK-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] 3,6-dichloro-2-methoxybenzoate Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(=O)ON1C2=CC(Cl)=CN=C2N=C1C(F)(F)F FYUQTKJEXWZHFK-UHFFFAOYSA-N 0.000 description 1
- MMPFJSMLKNXSRO-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] 3-amino-2,5-dichlorobenzoate Chemical compound NC1=CC(Cl)=CC(C(=O)ON2C3=CC(Cl)=CN=C3N=C2C(F)(F)F)=C1Cl MMPFJSMLKNXSRO-UHFFFAOYSA-N 0.000 description 1
- MRVQQJKJSGJJED-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] 3-phenylprop-2-enoate Chemical compound FC(F)(F)C1=NC2=NC=C(Cl)C=C2N1OC(=O)C=CC1=CC=CC=C1 MRVQQJKJSGJJED-UHFFFAOYSA-N 0.000 description 1
- QATLXOAEKJYTJI-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] octanoate Chemical compound C1=C(Cl)C=C2N(OC(=O)CCCCCCC)C(C(F)(F)F)=NC2=N1 QATLXOAEKJYTJI-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000012773 agricultural material Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 229960000892 attapulgite Drugs 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 239000002283 diesel fuel Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide 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
- 239000003350 kerosene Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- WNPVLQNVTLWJDG-UHFFFAOYSA-N n-(3,5-dinitropyridin-2-yl)-2,2-difluoroacetamide Chemical compound [O-][N+](=O)C1=CN=C(NC(=O)C(F)F)C([N+]([O-])=O)=C1 WNPVLQNVTLWJDG-UHFFFAOYSA-N 0.000 description 1
- ULMSSNSRSKYTNI-UHFFFAOYSA-N n-(5-bromo-3-nitropyridin-2-yl)-2-chloro-2,2-difluoroacetamide Chemical compound [O-][N+](=O)C1=CC(Br)=CN=C1NC(=O)C(F)(F)Cl ULMSSNSRSKYTNI-UHFFFAOYSA-N 0.000 description 1
- WPTVPDJOXQNELU-UHFFFAOYSA-N n-(5-butylsulfonyl-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide Chemical compound CCCCS(=O)(=O)C1=CN=C(NC(=O)C(F)(F)F)C([N+]([O-])=O)=C1 WPTVPDJOXQNELU-UHFFFAOYSA-N 0.000 description 1
- NVJNDBHULQUHLS-UHFFFAOYSA-N n-(5-ethylsulfonyl-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide Chemical compound CCS(=O)(=O)C1=CN=C(NC(=O)C(F)(F)F)C([N+]([O-])=O)=C1 NVJNDBHULQUHLS-UHFFFAOYSA-N 0.000 description 1
- BALMQUSTNMCDSD-UHFFFAOYSA-N n-[5-(difluoromethyl)-3-nitropyridin-2-yl]-2,2-difluoroacetamide Chemical compound [O-][N+](=O)C1=CC(C(F)F)=CN=C1NC(=O)C(F)F BALMQUSTNMCDSD-UHFFFAOYSA-N 0.000 description 1
- KUGQPKRCGZQODG-UHFFFAOYSA-N n-[5-[chloro(difluoro)methyl]-3-nitropyridin-2-yl]-2,2,3,3,4,4,4-heptafluorobutanamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)Cl)=CN=C1NC(=O)C(F)(F)C(F)(F)C(F)(F)F KUGQPKRCGZQODG-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 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
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- 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
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2153570A | 1970-03-20 | 1970-03-20 | |
| US10041070A | 1970-12-21 | 1970-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH542578A true CH542578A (de) | 1973-10-15 |
Family
ID=26694799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH407971A CH542578A (de) | 1970-03-20 | 1971-03-19 | Herbicides Mittel |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5320519B1 (enExample) |
| AT (1) | AT310491B (enExample) |
| CH (1) | CH542578A (enExample) |
| DK (1) | DK133377B (enExample) |
| EG (1) | EG10414A (enExample) |
| ES (1) | ES389343A1 (enExample) |
| HU (1) | HU163528B (enExample) |
| NL (1) | NL7103682A (enExample) |
| RO (1) | RO58089A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6137533U (ja) * | 1984-08-03 | 1986-03-08 | 日本電気株式会社 | 座標入力装置 |
-
1971
- 1971-03-09 EG EG10571A patent/EG10414A/xx active
- 1971-03-18 AT AT234871A patent/AT310491B/de not_active IP Right Cessation
- 1971-03-18 ES ES389343A patent/ES389343A1/es not_active Expired
- 1971-03-18 DK DK129871A patent/DK133377B/da unknown
- 1971-03-18 NL NL7103682A patent/NL7103682A/xx not_active Application Discontinuation
- 1971-03-19 HU HUEI000374 patent/HU163528B/hu unknown
- 1971-03-19 CH CH407971A patent/CH542578A/de not_active IP Right Cessation
- 1971-03-20 JP JP1610471A patent/JPS5320519B1/ja active Pending
- 1971-03-20 RO RO6634171A patent/RO58089A/ro unknown
-
1976
- 1976-09-11 JP JP10934476A patent/JPS5257323A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| RO58089A (enExample) | 1975-06-15 |
| JPS5257323A (en) | 1977-05-11 |
| DE2112776B2 (de) | 1975-07-24 |
| HU163528B (enExample) | 1973-09-27 |
| DK133377C (enExample) | 1976-10-11 |
| JPS5420575B2 (enExample) | 1979-07-24 |
| EG10414A (en) | 1976-01-31 |
| AT310491B (de) | 1973-10-10 |
| JPS5320519B1 (enExample) | 1978-06-27 |
| DK133377B (da) | 1976-05-10 |
| NL7103682A (enExample) | 1971-09-22 |
| DE2112776A1 (de) | 1971-12-09 |
| ES389343A1 (es) | 1975-05-16 |
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