JP7077314B2 - 硫黄およびヒドロキシルアミン置換基を有する有害生物防除的に活性な複素環式誘導体 - Google Patents
硫黄およびヒドロキシルアミン置換基を有する有害生物防除的に活性な複素環式誘導体 Download PDFInfo
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- JP7077314B2 JP7077314B2 JP2019522723A JP2019522723A JP7077314B2 JP 7077314 B2 JP7077314 B2 JP 7077314B2 JP 2019522723 A JP2019522723 A JP 2019522723A JP 2019522723 A JP2019522723 A JP 2019522723A JP 7077314 B2 JP7077314 B2 JP 7077314B2
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- 241000607479 Yersinia pestis Species 0.000 title claims description 31
- 229910052717 sulfur Inorganic materials 0.000 title description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 11
- 239000011593 sulfur Substances 0.000 title description 9
- 125000000623 heterocyclic group Chemical group 0.000 title description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 324
- 229910052736 halogen Inorganic materials 0.000 claims description 139
- 150000002367 halogens Chemical group 0.000 claims description 139
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 120
- 125000001424 substituent group Chemical group 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 61
- 125000001425 triazolyl group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 26
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 19
- 206010011703 Cyanosis Diseases 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000001850 reproductive effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000000361 pesticidal effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 1
- -1 C 4 alkane carboxylic acids Chemical class 0.000 description 147
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 110
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 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 description 51
- 239000000460 chlorine Substances 0.000 description 48
- 239000000126 substance Substances 0.000 description 48
- 230000002829 reductive effect Effects 0.000 description 47
- 239000000243 solution Substances 0.000 description 47
- 229910052801 chlorine Inorganic materials 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 39
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 39
- 229910052794 bromium Inorganic materials 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 231100000765 toxin Toxicity 0.000 description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
- 239000003053 toxin Substances 0.000 description 35
- 108700012359 toxins Proteins 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 32
- 239000012442 inert solvent Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 239000002585 base Substances 0.000 description 29
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- 125000001309 chloro group Chemical group Cl* 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 25
- 238000011161 development Methods 0.000 description 24
- 230000018109 developmental process Effects 0.000 description 24
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 23
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- 239000012043 crude product Substances 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 21
- 239000011630 iodine Substances 0.000 description 21
- 229910052740 iodine Inorganic materials 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 240000008042 Zea mays Species 0.000 description 18
- 241000894007 species Species 0.000 description 18
- 241000244206 Nematoda Species 0.000 description 17
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 125000004076 pyridyl group Chemical group 0.000 description 17
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 16
- 241000238631 Hexapoda Species 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 241001177134 Lyctus Species 0.000 description 15
- 229910052796 boron Inorganic materials 0.000 description 15
- 125000001153 fluoro group Chemical group F* 0.000 description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 125000001246 bromo group Chemical group Br* 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 11
- 229910000024 caesium carbonate Inorganic materials 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
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- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 11
- 230000009261 transgenic effect Effects 0.000 description 11
- 241001124076 Aphididae Species 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
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- 150000001340 alkali metals Chemical class 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 9
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- 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
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
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- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201611036908 | 2016-10-27 | ||
| IN201611036908 | 2016-10-27 | ||
| PCT/EP2017/074590 WO2018077565A1 (en) | 2016-10-27 | 2017-09-28 | Pesticidally active heterocyclic derivatives with sulphur and hydroxylamine substituents |
Publications (3)
| Publication Number | Publication Date |
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| JP2020500170A JP2020500170A (ja) | 2020-01-09 |
| JP2020500170A5 JP2020500170A5 (enExample) | 2020-11-12 |
| JP7077314B2 true JP7077314B2 (ja) | 2022-05-30 |
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| JP2019522723A Active JP7077314B2 (ja) | 2016-10-27 | 2017-09-28 | 硫黄およびヒドロキシルアミン置換基を有する有害生物防除的に活性な複素環式誘導体 |
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| US (2) | US10889583B2 (enExample) |
| EP (1) | EP3532471B1 (enExample) |
| JP (1) | JP7077314B2 (enExample) |
| CN (2) | CN109890818B (enExample) |
| AR (1) | AR109868A1 (enExample) |
| BR (1) | BR112019008492B1 (enExample) |
| ES (1) | ES2902732T3 (enExample) |
| WO (1) | WO2018077565A1 (enExample) |
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| US10071997B2 (en) * | 2014-12-01 | 2018-09-11 | Syngenta Participations Ag | Pesticidally active amide heterocyclic derivatives with sulphur containing substituents |
| TWI793104B (zh) * | 2017-02-21 | 2023-02-21 | 瑞士商先正達合夥公司 | 具有含硫取代基的殺有害生物活性雜環衍生物 |
| US11413291B2 (en) * | 2017-09-18 | 2022-08-16 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| JP7536656B2 (ja) * | 2018-06-06 | 2024-08-20 | 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 | スルホキシイミン含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
| US20220061324A1 (en) | 2018-12-31 | 2022-03-03 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| TW202045011A (zh) | 2019-02-28 | 2020-12-16 | 瑞士商先正達農作物保護公司 | 具有含硫取代基之殺有害生物活性雜環衍生物 |
| BR112022021895A2 (pt) * | 2020-04-30 | 2023-01-24 | Syngenta Crop Protection Ag | Derivados heterocíclicos com substituintes contendo enxofre ativos em termos pesticidas |
| WO2022013417A1 (en) | 2020-07-17 | 2022-01-20 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2022017975A1 (en) | 2020-07-18 | 2022-01-27 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| EP4204422A1 (en) | 2020-08-26 | 2023-07-05 | Syngenta Crop Protection AG | Process for the preparation of 2,2-difluoro-1,3-benzodioxole derivatives with sulfur containing substituents |
| UY39404A (es) | 2020-09-02 | 2022-03-31 | Syngenta Crop Protection Ag | Derivados de 2,2-diflúor-5h-[1,3]dioxol[4,5-f]isoindol-7-ona activos como plaguicidas con sustituyentes que contienen azufre |
| IL309024A (en) | 2021-06-02 | 2024-02-01 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
| CR20240132A (es) | 2021-09-13 | 2024-06-20 | Boehringer Ingelheim Vetmedica Gmbh | Derivados de etilsulfonil-piridina sustituidos con ciclopropil-(hetero)arilo |
| CN114478449B (zh) * | 2022-01-19 | 2023-10-27 | 江苏海洋大学 | 一种多取代含硒二氢异苯并呋喃衍生物及其制备方法 |
| WO2024156664A1 (en) | 2023-01-23 | 2024-08-02 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2024175558A1 (en) | 2023-02-23 | 2024-08-29 | Boehringer Ingelheim Vetmedica Gmbh | Cyclopropyl-(hetero)aryl-substituted ethyl-sulfone/sulfoximine-pyridine n-oxide derivatives |
| CN120882309A (zh) | 2023-03-14 | 2025-10-31 | 先正达农作物保护股份公司 | 对杀昆虫剂具有抗性的有害生物的控制 |
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-
2017
- 2017-09-28 WO PCT/EP2017/074590 patent/WO2018077565A1/en not_active Ceased
- 2017-09-28 US US16/345,709 patent/US10889583B2/en active Active
- 2017-09-28 CN CN201780066977.5A patent/CN109890818B/zh active Active
- 2017-09-28 JP JP2019522723A patent/JP7077314B2/ja active Active
- 2017-09-28 EP EP17784208.5A patent/EP3532471B1/en active Active
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- 2017-09-28 ES ES17784208T patent/ES2902732T3/es active Active
- 2017-09-28 CN CN202210131282.3A patent/CN114456164B/zh active Active
- 2017-10-23 AR ARP170102945A patent/AR109868A1/es unknown
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2020
- 2020-10-29 US US17/083,490 patent/US12152024B2/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009528989A (ja) | 2006-02-17 | 2009-08-13 | ファイザー・リミテッド | Tlr7変調剤としての3−デアザプリン誘導体 |
| WO2014142292A1 (ja) | 2013-03-15 | 2014-09-18 | 日本農薬株式会社 | 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
| WO2016023954A2 (en) | 2014-08-12 | 2016-02-18 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| WO2016107831A1 (en) | 2014-12-31 | 2016-07-07 | Syngenta Crop Protection Ag | Pesticidally active polycyclic derivatives with sulfur containing substituents |
| WO2016142326A1 (en) | 2015-03-12 | 2016-09-15 | Syngenta Participations Ag | Pesticidally active tetracyclic derivatives with sulfur containing substituents |
Also Published As
| Publication number | Publication date |
|---|---|
| US20210053970A1 (en) | 2021-02-25 |
| CN114456164A (zh) | 2022-05-10 |
| US20190352299A1 (en) | 2019-11-21 |
| EP3532471B1 (en) | 2021-09-15 |
| US10889583B2 (en) | 2021-01-12 |
| US12152024B2 (en) | 2024-11-26 |
| WO2018077565A1 (en) | 2018-05-03 |
| BR112019008492B1 (pt) | 2024-01-30 |
| AR109868A1 (es) | 2019-01-30 |
| JP2020500170A (ja) | 2020-01-09 |
| CN109890818B (zh) | 2022-11-25 |
| CN114456164B (zh) | 2024-03-12 |
| BR112019008492A2 (pt) | 2019-07-09 |
| ES2902732T3 (es) | 2022-03-29 |
| EP3532471A1 (en) | 2019-09-04 |
| CN109890818A (zh) | 2019-06-14 |
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