UA125599C2 - Гербіцидні сполуки - Google Patents
Гербіцидні сполуки Download PDFInfo
- Publication number
- UA125599C2 UA125599C2 UAA202001679A UAA202001679A UA125599C2 UA 125599 C2 UA125599 C2 UA 125599C2 UA A202001679 A UAA202001679 A UA A202001679A UA A202001679 A UAA202001679 A UA A202001679A UA 125599 C2 UA125599 C2 UA 125599C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- group
- compound
- mhz
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 260
- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims description 185
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 239000001257 hydrogen Substances 0.000 claims description 109
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 63
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- DBNKMEZCQQZZBD-UHFFFAOYSA-N 2-pyridazin-4-ylpyrimidine Chemical compound N1=CC=CN=C1C1=CC=NN=C1 DBNKMEZCQQZZBD-UHFFFAOYSA-N 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 239000012634 fragment Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000012010 growth Effects 0.000 claims description 8
- 125000002577 pseudohalo group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- WVIMSFDSAWGNPE-UHFFFAOYSA-N 2-pyridazin-4-ylpyrazine Chemical compound C1=NC=CN=C1C1=CC=NN=C1 WVIMSFDSAWGNPE-UHFFFAOYSA-N 0.000 claims description 6
- PKILSTFBXYVVTA-UHFFFAOYSA-N 3-pyridazin-4-ylpyridazine Chemical compound C1=CN=NC(C=2C=NN=CC=2)=C1 PKILSTFBXYVVTA-UHFFFAOYSA-N 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- XXTYHAFSJIWNJN-UHFFFAOYSA-N 4-pyridazin-4-ylpyrimidine Chemical compound N1=CN=C(C=C1)C1=CN=NC=C1 XXTYHAFSJIWNJN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims description 3
- RFFQGKVABDVQQE-UHFFFAOYSA-N 4-pyridazin-4-ylpyridazine Chemical compound N1=NC=CC(C=2C=NN=CC=2)=C1 RFFQGKVABDVQQE-UHFFFAOYSA-N 0.000 claims description 2
- 239000012872 agrochemical composition Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 12
- 239000000575 pesticide Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 170
- 238000002360 preparation method Methods 0.000 description 140
- 239000011541 reaction mixture Substances 0.000 description 139
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
- 238000005481 NMR spectroscopy Methods 0.000 description 84
- 239000000243 solution Substances 0.000 description 76
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 75
- 239000007787 solid Substances 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- -1 hydrocarbon radical Chemical class 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 50
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000004480 active ingredient Substances 0.000 description 33
- 239000000377 silicon dioxide Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000012071 phase Substances 0.000 description 25
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 16
- JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 description 16
- KDKIWFRRJZZYRP-UHFFFAOYSA-N 1-hydroxypropane-2-sulfonic acid Chemical compound OCC(C)S(O)(=O)=O KDKIWFRRJZZYRP-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 13
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 235000019260 propionic acid Nutrition 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 238000006880 cross-coupling reaction Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002202 Polyethylene glycol Chemical class 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
- 229920001223 polyethylene glycol Chemical class 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- KCXFHTAICRTXLI-UHFFFAOYSA-M propane-1-sulfonate Chemical compound CCCS([O-])(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000004007 reversed phase HPLC Methods 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- UDLLSOQWYYRFPP-UHFFFAOYSA-N tributyl(pyridazin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NN=C1 UDLLSOQWYYRFPP-UHFFFAOYSA-N 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- AIECIGJELMYJMO-UHFFFAOYSA-N ClC=1C=NC(=NC=1)C1=CN=NC=C1 Chemical compound ClC=1C=NC(=NC=1)C1=CN=NC=C1 AIECIGJELMYJMO-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000004108 freeze drying Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003094 microcapsule Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 4
- KNIBMLHGILXPOS-UHFFFAOYSA-N 2,2-dimethylpropyl methanesulfonate Chemical compound CC(C)(C)COS(C)(=O)=O KNIBMLHGILXPOS-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- ALZCALONBOWFAG-UHFFFAOYSA-N 2-(trifluoromethylsulfonyloxy)propane-1-sulfonic acid Chemical compound FC(S(=O)(=O)OC(CS(=O)(=O)O)C)(F)F ALZCALONBOWFAG-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 4
- UHRQBFSVNFOVTF-UHFFFAOYSA-N CC(C)(C)CC(CNNC(OC(C)(C)C)=O)S(O)(=O)=O Chemical compound CC(C)(C)CC(CNNC(OC(C)(C)C)=O)S(O)(=O)=O UHRQBFSVNFOVTF-UHFFFAOYSA-N 0.000 description 4
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OOLZXLYYPCOPQZ-UHFFFAOYSA-N tripropylsulfanium Chemical compound CCC[S+](CCC)CCC OOLZXLYYPCOPQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201711029217 | 2017-08-17 | ||
| PCT/EP2018/072280 WO2019034757A1 (en) | 2017-08-17 | 2018-08-16 | HERBICIDE COMPOUNDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA125599C2 true UA125599C2 (uk) | 2022-04-27 |
Family
ID=63244619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA202001679A UA125599C2 (uk) | 2017-08-17 | 2018-08-16 | Гербіцидні сполуки |
Country Status (33)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR114422A1 (es) * | 2018-03-30 | 2020-09-02 | Syngenta Participations Ag | Compuestos herbicidas |
| CA3118623A1 (en) | 2018-11-12 | 2020-05-22 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201901617D0 (en) * | 2019-02-06 | 2019-03-27 | Syngenta Crop Protection Ag | Herbicidal compounds |
| WO2020161209A1 (en) * | 2019-02-06 | 2020-08-13 | Syngenta Crop Protection Ag | Herbicidal fused pyridazine compounds |
| WO2020161208A1 (en) * | 2019-02-06 | 2020-08-13 | Syngenta Crop Protection Ag | Herbicidal fused pyridazine compounds |
| GB201901760D0 (en) * | 2019-02-08 | 2019-03-27 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201901866D0 (en) * | 2019-02-11 | 2019-04-03 | Syngenta Crop Protection Ag | Pre-harvest desiccation method |
| GB201902064D0 (en) * | 2019-02-14 | 2019-04-03 | Syngenta Crop Protection Ag | Herbicidal compounds |
| CN113423272A (zh) * | 2019-02-15 | 2021-09-21 | 先正达农作物保护股份公司 | 除草组合物 |
| CA3128436A1 (en) * | 2019-02-15 | 2020-08-20 | Syngenta Crop Protection Ag | Herbicidal compositions |
| AU2020222195A1 (en) * | 2019-02-15 | 2021-09-09 | Syngenta Crop Protection Ag | Herbicidal compositions |
| GB201902107D0 (en) * | 2019-02-15 | 2019-04-03 | Syngenta Crop Protection Ag | Herbicidal compounds |
| EP3923726A1 (en) * | 2019-02-15 | 2021-12-22 | Syngenta Crop Protection AG | Herbicidal compositions |
| EP3923725A1 (en) * | 2019-02-15 | 2021-12-22 | Syngenta Crop Protection AG | Herbicidal compositions |
| GB201903000D0 (en) * | 2019-03-06 | 2019-04-17 | Syngenta Crop Protection Ag | Herbicidal compounds |
| CN111820224B (zh) * | 2019-04-22 | 2022-04-05 | 江苏清原农冠杂草防治有限公司 | 包含三氟甲基哒嗪醇类化合物的除草组合物及其应用 |
| CN113939499A (zh) * | 2019-06-11 | 2022-01-14 | 福提费斯特有限公司 | 新型非编码杂环氨基酸(nchaa)及其作为除草剂的用途 |
| GB201913752D0 (en) * | 2019-09-24 | 2019-11-06 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201913750D0 (en) * | 2019-09-24 | 2019-11-06 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB202000878D0 (en) * | 2020-01-21 | 2020-03-04 | Syngenta Crop Protection Ag | Chemical process |
| GB202007594D0 (en) | 2020-05-21 | 2020-07-08 | Syngenta Crop Protection Ag | Chemical process |
| GB202007595D0 (en) | 2020-05-21 | 2020-07-08 | Syngenta Crop Protection Ag | Chemical process |
| TW202214106A (zh) * | 2020-08-14 | 2022-04-16 | 瑞士商先正達農作物保護公司 | 化學方法 |
| TW202222163A (zh) | 2020-08-14 | 2022-06-16 | 瑞士商先正達農作物保護公司 | 化學方法 |
| MX2024000051A (es) | 2021-07-09 | 2024-02-21 | Syngenta Crop Protection Ag | Composiciones herbicidas. |
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| US3702361A (en) * | 1969-11-21 | 1972-11-07 | Monsanto Co | Insecticidal methods using n-substituted heterocyclic phenacyl halides and ylids |
| DE2003461A1 (de) * | 1970-01-27 | 1971-08-05 | Basf Ag | Verfahren zur Herstellung von 2-Alkylpyridaziniumverbindungen |
| CH621348A5 (enExample) | 1976-05-04 | 1981-01-30 | Ciba Geigy Ag | |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| NZ231804A (en) | 1988-12-19 | 1993-03-26 | Ciba Geigy Ag | Insecticidal toxin from leiurus quinquestriatus hebraeus |
| DK0427529T3 (da) | 1989-11-07 | 1995-06-26 | Pioneer Hi Bred Int | Larvedræbende lactiner og planteinsektresistens baseret derpå |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| US5466697A (en) | 1994-07-13 | 1995-11-14 | Syntex (U.S.A.) Inc. | 8-phenyl-1,6-naphthyridin-5-ones |
| DE10024938A1 (de) * | 2000-05-19 | 2001-11-22 | Bayer Ag | Substituierte Iminoazine |
| AR031027A1 (es) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
| AR037856A1 (es) | 2001-12-17 | 2004-12-09 | Syngenta Participations Ag | Evento de maiz |
| DE102005029094A1 (de) | 2005-06-23 | 2007-01-04 | Basf Ag | Verfahren zur Herstellung von Pyridazin |
| CN102171204B (zh) | 2008-10-02 | 2014-08-20 | 旭化成制药株式会社 | 8位取代异喹啉衍生物及其用途 |
| WO2015066371A1 (en) | 2013-10-31 | 2015-05-07 | Forum Pharmaceuticals, Inc. | SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
| KR102164031B1 (ko) | 2014-05-22 | 2020-10-13 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| GB201419826D0 (en) * | 2014-11-07 | 2014-12-24 | Syngenta Participations Ag | Herbicidal compounds |
| CN104961686B (zh) | 2015-05-18 | 2017-12-05 | 华中师范大学 | 1,6‑二氢哒嗪和哒嗪类化合物的合成方法及其在五种常见致病真菌生长活性抑制中的应用 |
| AR114422A1 (es) * | 2018-03-30 | 2020-09-02 | Syngenta Participations Ag | Compuestos herbicidas |
-
2018
- 2018-08-14 AR ARP180102305 patent/AR112682A1/es not_active Application Discontinuation
- 2018-08-15 TW TW107128463A patent/TWI784038B/zh not_active IP Right Cessation
- 2018-08-16 ES ES18755818T patent/ES2905904T3/es active Active
- 2018-08-16 MY MYPI2020000417A patent/MY199853A/en unknown
- 2018-08-16 UY UY0001037849A patent/UY37849A/es not_active Application Discontinuation
- 2018-08-16 CU CU2020000013A patent/CU24612B1/es unknown
- 2018-08-16 JP JP2020508608A patent/JP7289827B2/ja active Active
- 2018-08-16 BR BR112020003047-3A patent/BR112020003047A2/pt not_active Application Discontinuation
- 2018-08-16 WO PCT/EP2018/072280 patent/WO2019034757A1/en not_active Ceased
- 2018-08-16 EA EA202090479A patent/EA202090479A1/ru unknown
- 2018-08-16 HU HUE18755818A patent/HUE057239T2/hu unknown
- 2018-08-16 PL PL18755818T patent/PL3668855T3/pl unknown
- 2018-08-16 CR CR20200075A patent/CR20200075A/es unknown
- 2018-08-16 PH PH1/2020/500150A patent/PH12020500150B1/en unknown
- 2018-08-16 DK DK18755818.4T patent/DK3668855T3/da active
- 2018-08-16 KR KR1020207007187A patent/KR20200042491A/ko not_active Abandoned
- 2018-08-16 UA UAA202001679A patent/UA125599C2/uk unknown
- 2018-08-16 CN CN201880053132.7A patent/CN111032640B/zh not_active Expired - Fee Related
- 2018-08-16 HR HRP20220140TT patent/HRP20220140T1/hr unknown
- 2018-08-16 EP EP18755818.4A patent/EP3668855B1/en active Active
- 2018-08-16 RS RS20220116A patent/RS62888B1/sr unknown
- 2018-08-16 MX MX2020001731A patent/MX2020001731A/es unknown
- 2018-08-16 AU AU2018316526A patent/AU2018316526B2/en not_active Ceased
- 2018-08-16 PT PT187558184T patent/PT3668855T/pt unknown
- 2018-08-16 MA MA049900A patent/MA49900A/fr unknown
- 2018-08-16 CA CA3071643A patent/CA3071643A1/en active Pending
- 2018-08-16 US US16/639,723 patent/US11618743B2/en active Active
-
2020
- 2020-02-04 ZA ZA2020/00717A patent/ZA202000717B/en unknown
- 2020-02-11 CL CL2020000357A patent/CL2020000357A1/es unknown
- 2020-02-13 CO CONC2020/0001631A patent/CO2020001631A2/es unknown
- 2020-02-13 IL IL272665A patent/IL272665B/en unknown
- 2020-02-14 NI NI202000012A patent/NI202000012A/es unknown
- 2020-02-14 EC ECSENADI202011470A patent/ECSP20011470A/es unknown
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