TWI713704B - 殺微生物的喹啉（硫代）羧醯胺衍生物 - Google Patents
殺微生物的喹啉（硫代）羧醯胺衍生物 Download PDFInfo
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- TWI713704B TWI713704B TW106107562A TW106107562A TWI713704B TW I713704 B TWI713704 B TW I713704B TW 106107562 A TW106107562 A TW 106107562A TW 106107562 A TW106107562 A TW 106107562A TW I713704 B TWI713704 B TW I713704B
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- Prior art keywords
- methyl
- group
- alkyl
- fluorine
- independently selected
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- 150000001875 compounds Chemical class 0.000 claims abstract description 287
- 239000000203 mixture Substances 0.000 claims abstract description 109
- 239000000463 material Substances 0.000 claims abstract description 23
- 239000011737 fluorine Substances 0.000 claims description 140
- 229910052731 fluorine Inorganic materials 0.000 claims description 140
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 139
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 139
- -1 cyano, methanoyl Chemical group 0.000 claims description 137
- 239000001257 hydrogen Substances 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 82
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 81
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 73
- 239000000460 chlorine Substances 0.000 claims description 71
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 67
- 229910052801 chlorine Inorganic materials 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 53
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 43
- 150000001204 N-oxides Chemical class 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 41
- 239000004480 active ingredient Substances 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 20
- 125000005336 allyloxy group Chemical group 0.000 claims description 19
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- SPDIXQXJBZYVFU-UHFFFAOYSA-N 7,8-difluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F SPDIXQXJBZYVFU-UHFFFAOYSA-N 0.000 claims description 3
- SGSTZURMXPJQSD-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-8-fluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(=C)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F SGSTZURMXPJQSD-UHFFFAOYSA-N 0.000 claims description 3
- VMSKKUQFMJAMHW-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=CC=CC=C2C=1 VMSKKUQFMJAMHW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims 2
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
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- MPXHQDZAKMYKDH-UHFFFAOYSA-N 8-fluoro-N-(4-fluoro-2,4-dimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)(C)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F MPXHQDZAKMYKDH-UHFFFAOYSA-N 0.000 claims 1
- DTOZPNHGPWULBM-UHFFFAOYSA-N 8-fluoro-N-[1-(3-fluorophenyl)-2,4-dimethylpentan-2-yl]quinoline-3-carboxamide Chemical compound FC=1C=CC=C2C=C(C=NC=12)C(=O)NC(CC(C)C)(C)CC1=CC(=CC=C1)F DTOZPNHGPWULBM-UHFFFAOYSA-N 0.000 claims 1
- RLXNCCMFGMORFD-UHFFFAOYSA-N 8-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)C RLXNCCMFGMORFD-UHFFFAOYSA-N 0.000 claims 1
- UDHYKSDZPGKEBP-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-7,8-difluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(=C)C)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F UDHYKSDZPGKEBP-UHFFFAOYSA-N 0.000 claims 1
- GQKJCCBWMYAKOY-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpentan-2-yl)-7,8-difluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F GQKJCCBWMYAKOY-UHFFFAOYSA-N 0.000 claims 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000002708 spider venom Substances 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 108010076424 stilbene synthase Proteins 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000021918 systemic acquired resistance Effects 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000004558 technical concentrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- INWVNNCOIIHEPX-UHFFFAOYSA-N thiadiazole-4-carboxamide Chemical compound NC(=O)C1=CSN=N1 INWVNNCOIIHEPX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- QPDUQKTYZRXRBC-UHFFFAOYSA-N triazole-4-thione Chemical compound S=C1C=NN=N1 QPDUQKTYZRXRBC-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16159707.5 | 2016-03-10 | ||
| EP16159707 | 2016-03-10 | ||
| EP17154212 | 2017-02-01 | ||
| EP17154212.9 | 2017-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201733986A TW201733986A (zh) | 2017-10-01 |
| TWI713704B true TWI713704B (zh) | 2020-12-21 |
Family
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|---|---|---|---|
| TW106107562A TWI713704B (zh) | 2016-03-10 | 2017-03-08 | 殺微生物的喹啉（硫代）羧醯胺衍生物 |
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| BR (1) | BR112018068206B1 (enExample) |
| CA (1) | CA3015449C (enExample) |
| CL (1) | CL2018002569A1 (enExample) |
| CO (1) | CO2018009292A2 (enExample) |
| CR (1) | CR20180434A (enExample) |
| CY (1) | CY1124390T1 (enExample) |
| DK (1) | DK3426032T3 (enExample) |
| ES (1) | ES2826477T3 (enExample) |
| GE (1) | GEP20207183B (enExample) |
| HR (1) | HRP20201657T1 (enExample) |
| HU (1) | HUE050995T2 (enExample) |
| IL (1) | IL261122B (enExample) |
| LT (1) | LT3426032T (enExample) |
| MX (1) | MX376002B (enExample) |
| PT (1) | PT3426032T (enExample) |
| RS (1) | RS60932B1 (enExample) |
| SI (1) | SI3426032T1 (enExample) |
| TW (1) | TWI713704B (enExample) |
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| ZA (1) | ZA201805488B (enExample) |
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| ES2908668T3 (es) * | 2017-09-13 | 2022-05-03 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
| CN111107745B (zh) * | 2017-09-13 | 2021-12-07 | 先正达参股股份有限公司 | 杀真菌组合物 |
| MA50787A (fr) | 2017-11-21 | 2020-09-30 | Syngenta Participations Ag | Compositions fongicides |
| BR112021005684A2 (pt) * | 2018-09-26 | 2021-06-22 | Syngenta Crop Protection Ag | composições fungicidas |
| WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
| JP2022504304A (ja) * | 2018-10-06 | 2022-01-13 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリンジヒドロ－（チアジン）オキサジン誘導体 |
| WO2020165403A1 (en) | 2019-02-15 | 2020-08-20 | Syngenta Crop Protection Ag | Phenyl substituted thiazole derivatives as microbiocidal compounds |
| EP3935053B1 (en) | 2019-03-08 | 2023-06-07 | Syngenta Crop Protection AG | Pesticidally active azole-amide compounds |
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| JP2022525809A (ja) | 2019-03-22 | 2022-05-19 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺虫剤としてのｎ－［１－（５－ブロモ－２－ピリミジン－２－イル－１，２，４－トリアゾール－３－イル）エチル］－２－シクロプロピル－６－（トリフルオロメチル）ピリジン－４－カルボキサミド誘導体及び関連化合物 |
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| KR20210149113A (ko) | 2019-04-05 | 2021-12-08 | 신젠타 크롭 프로텍션 아게 | 살충 활성 디아진-아미드 화합물 |
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| CN113939510A (zh) | 2019-05-29 | 2022-01-14 | 先正达农作物保护股份公司 | 杀微生物衍生物 |
| CN113924294B (zh) | 2019-05-29 | 2024-12-06 | 先正达农作物保护股份公司 | 杀微生物衍生物 |
| AR119011A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | DERIVADOS DE [1,3]DIOXOLO[4,5-c]PIRIDIN-4-CARBOXAMIDA, COMPOSICIONES AGROQUÍMICAS QUE LOS COMPRENDEN Y SU EMPLEO COMO FUNGICIDA PARA CONTROLAR O PREVENIR LA INFESTACIÓN DE PLANTAS ÚTILES |
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| BR112022012873A2 (pt) | 2019-12-31 | 2022-09-06 | Syngenta Crop Protection Ag | Derivados heterocíclicos ativos em termos pesticidas com substituintes contendo enxofre |
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| JP2023511201A (ja) | 2020-01-24 | 2023-03-16 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性な縮合二環式芳香族複素環式化合物 |
| CN115135647A (zh) | 2020-01-30 | 2022-09-30 | 先正达农作物保护股份公司 | 杀有害生物活性的稠合二环杂芳香族氨基化合物 |
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| CN115702149B (zh) | 2020-04-30 | 2025-08-19 | 先正达农作物保护股份公司 | 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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| EP4153566A1 (en) * | 2020-05-19 | 2023-03-29 | Bayer CropScience Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
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| AR124276A1 (es) | 2020-10-22 | 2023-03-15 | Syngenta Crop Protection Ag | Compuestos reguladores del crecimiento vegetal |
| WO2022101265A1 (en) | 2020-11-13 | 2022-05-19 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
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