JP6871917B2 - 有害生物防除剤としての２−（ヘタ）アリール−置換縮合二環式ヘテロ環誘導体 - Google Patents
有害生物防除剤としての２−（ヘタ）アリール−置換縮合二環式ヘテロ環誘導体 Download PDFInfo
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- JP6871917B2 JP6871917B2 JP2018515805A JP2018515805A JP6871917B2 JP 6871917 B2 JP6871917 B2 JP 6871917B2 JP 2018515805 A JP2018515805 A JP 2018515805A JP 2018515805 A JP2018515805 A JP 2018515805A JP 6871917 B2 JP6871917 B2 JP 6871917B2
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 title 1
- 230000005494 condensation Effects 0.000 title 1
- 238000009833 condensation Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 302
- 238000002360 preparation method Methods 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 239000000575 pesticide Substances 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000004067 bulking agent Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- -1 cyano, nitro, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 description 165
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- 239000000203 mixture Substances 0.000 description 66
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- 241000894007 species Species 0.000 description 57
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 229910052736 halogen Inorganic materials 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 46
- 150000002367 halogens Chemical class 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 238000012360 testing method Methods 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 238000009472 formulation Methods 0.000 description 25
- 239000000843 powder Substances 0.000 description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 24
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 24
- 235000003550 Dracunculus Nutrition 0.000 description 24
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 23
- 241000224003 Sarcocystis Species 0.000 description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- 125000004093 cyano group Chemical group *C#N 0.000 description 23
- 239000003112 inhibitor Substances 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 18
- 238000000576 coating method Methods 0.000 description 18
- 125000001072 heteroaryl group Chemical group 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
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- 206010024503 Limb reduction defect Diseases 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000005159 cyanoalkoxy group Chemical group 0.000 description 16
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 14
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- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 239000003085 diluting agent Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 230000009261 transgenic effect Effects 0.000 description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 125000003545 alkoxy group Chemical group 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 11
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- 241001453380 Burkholderia Species 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 241000189565 Frankliniella Species 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 241000722234 Pseudococcus Species 0.000 description 11
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- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 11
- 125000000262 haloalkenyl group Chemical group 0.000 description 11
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
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- 235000011181 potassium carbonates Nutrition 0.000 description 11
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- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- 125000003282 alkyl amino group Chemical group 0.000 description 10
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
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- 125000005842 heteroatom Chemical group 0.000 description 10
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 10
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
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- 150000003839 salts Chemical class 0.000 description 9
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| EP15187145.6 | 2015-09-28 | ||
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| PCT/EP2016/072697 WO2017055185A1 (de) | 2015-09-28 | 2016-09-23 | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
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| JP2018529702A5 JP2018529702A5 (cg-RX-API-DMAC7.html) | 2019-10-31 |
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| CN109996799B (zh) | 2016-08-15 | 2022-07-19 | 拜耳作物科学股份公司 | 作为害虫防治剂的稠合双环杂环衍生物 |
| TW201833107A (zh) * | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物 |
| TWI762568B (zh) | 2017-02-06 | 2022-05-01 | 德商拜耳作物科學股份有限公司 | 製備鹵化咪唑並吡啶衍生物之方法 |
| EP3653624B1 (en) * | 2017-07-13 | 2022-12-07 | Sumitomo Chemical Company, Limited | Heterocyclic compound and harmful-arthropod control agent containing same |
| EP3733672B1 (en) | 2017-12-25 | 2023-03-22 | Sumitomo Chemical Company, Limited | Heterocyclic compounds and noxious arthropod control agent containing same |
| JP7274424B2 (ja) | 2017-12-26 | 2023-05-16 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
| CN111836810B (zh) * | 2018-01-15 | 2024-06-25 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
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| WO2021009311A1 (en) | 2019-07-17 | 2021-01-21 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
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| CN111825585B (zh) | 2019-09-23 | 2021-12-14 | 山东康乔生物科技有限公司 | 一种含苄胺结构的芳基硫化物及其合成方法和应用 |
| CN112824402B (zh) * | 2019-11-21 | 2023-02-28 | 浙江省化工研究院有限公司 | 一类苯并咪唑类衍生物、其制备方法及应用 |
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| TW202200570A (zh) * | 2020-04-21 | 2022-01-01 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２—（雜）芳基取代的稠合雜環衍生物 |
| CN116940236A (zh) * | 2021-02-07 | 2023-10-24 | 山东康乔生物科技有限公司 | 含有苄胺类杀螨剂的组合物及其应用 |
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| EP2873668A1 (en) | 2013-11-13 | 2015-05-20 | Syngenta Participations AG. | Pesticidally active bicyclic heterocycles with sulphur containing substituents |
| JP6469111B2 (ja) | 2013-12-20 | 2019-02-13 | シンジェンタ パーティシペーションズ アーゲー | 有害生物防除活性を有する硫黄含有置換基を伴う置換５，５−二環式複素環 |
| ES2987367T3 (es) * | 2014-02-17 | 2024-11-14 | Bayer Cropscience Ag | Derivados de heterociclos bicíclicos condensados sustituidos con 2-(het)arilo como agentes para combatir parásitos |
| AR099677A1 (es) | 2014-03-07 | 2016-08-10 | Sumitomo Chemical Co | Compuesto heterocíclico fusionado y su uso para el control de plagas |
| WO2015198859A1 (ja) | 2014-06-26 | 2015-12-30 | 住友化学株式会社 | 縮合複素環化合物 |
| EP3160962B1 (en) | 2014-06-26 | 2018-09-26 | Sumitomo Chemical Company, Limited | Method for producing fused heterocyclic compound |
| MX2017000305A (es) | 2014-07-08 | 2017-04-27 | Syngenta Participations Ag | Derivados heterociclicos activos con sustituyentes que contienen azufre como plaguicidas. |
| US9949483B2 (en) | 2014-08-07 | 2018-04-24 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| CN107074846B (zh) | 2014-08-12 | 2020-05-19 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
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| TW201625522A (zh) | 2014-09-12 | 2016-07-16 | Nihon Nohyaku Co Ltd | 咪唑嗒化合物或其鹽類及含有該化合物之農園藝用殺蟲劑及其使用方法 |
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| WO2016046071A1 (en) | 2014-09-25 | 2016-03-31 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| GB2535976C (en) | 2015-02-02 | 2017-03-29 | Drayson Tech (Europe) Ltd | Inverter for inductive power transfer |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019502713A (ja) * | 2016-01-11 | 2019-01-31 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としてのヘテロサイクレン誘導体 |
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| US20180303097A1 (en) | 2018-10-25 |
| TW201726672A (zh) | 2017-08-01 |
| ES2866911T3 (es) | 2021-10-20 |
| PH12018500638B1 (en) | 2022-06-03 |
| CL2018000741A1 (es) | 2019-04-26 |
| BR112018006198A2 (pt) | 2018-10-09 |
| AU2016330299A1 (en) | 2018-04-12 |
| EP3356362A1 (de) | 2018-08-08 |
| PE20181094A1 (es) | 2018-07-09 |
| CA2999790A1 (en) | 2017-04-06 |
| CN108290886A (zh) | 2018-07-17 |
| RU2018116054A (ru) | 2019-10-28 |
| UY36918A (es) | 2017-04-28 |
| IL258089A (en) | 2018-05-31 |
| AU2016330299B2 (en) | 2020-04-30 |
| AR106165A1 (es) | 2017-12-20 |
| TWI720023B (zh) | 2021-03-01 |
| BR112018006198B1 (pt) | 2022-05-31 |
| MX2018003761A (es) | 2018-07-06 |
| ZA201802797B (en) | 2020-01-29 |
| WO2017055185A1 (de) | 2017-04-06 |
| EP3356362B1 (de) | 2021-02-03 |
| US10745398B2 (en) | 2020-08-18 |
| KR20180054680A (ko) | 2018-05-24 |
| CO2018003427A2 (es) | 2018-06-12 |
| CN108290886B (zh) | 2020-11-03 |
| JP2018529702A (ja) | 2018-10-11 |
| PH12018500638A1 (en) | 2018-10-01 |
| KR102629107B1 (ko) | 2024-01-24 |
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