JP6685280B2 - 硫黄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 - Google Patents
硫黄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 Download PDFInfo
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- JP6685280B2 JP6685280B2 JP2017506756A JP2017506756A JP6685280B2 JP 6685280 B2 JP6685280 B2 JP 6685280B2 JP 2017506756 A JP2017506756 A JP 2017506756A JP 2017506756 A JP2017506756 A JP 2017506756A JP 6685280 B2 JP6685280 B2 JP 6685280B2
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- alkyl
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- halogen
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- 125000001424 substituent group Chemical group 0.000 title claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 227
- 229910052736 halogen Inorganic materials 0.000 claims description 134
- 150000002367 halogens Chemical class 0.000 claims description 133
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 127
- 239000000203 mixture Substances 0.000 claims description 115
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 70
- -1 stereoisomers Chemical class 0.000 claims description 65
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 51
- 239000004480 active ingredient Substances 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 42
- 241000607479 Yersinia pestis Species 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 22
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 21
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 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 20
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical class 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000000361 pesticidal effect Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004740 (C1-C6) haloalkylsulfanyl group Chemical group 0.000 claims description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 238000002405 diagnostic procedure Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 59
- 239000000126 substance Substances 0.000 description 58
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 53
- 150000002431 hydrogen Chemical class 0.000 description 52
- 241000196324 Embryophyta Species 0.000 description 48
- 239000000243 solution Substances 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 231100000765 toxin Toxicity 0.000 description 36
- 239000003053 toxin Substances 0.000 description 35
- 108700012359 toxins Proteins 0.000 description 35
- 229910001868 water Inorganic materials 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- 235000019439 ethyl acetate Nutrition 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000011161 development Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
- 240000008042 Zea mays Species 0.000 description 23
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 23
- 241000254173 Coleoptera Species 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 20
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 241000238631 Hexapoda Species 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 17
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- 241000193388 Bacillus thuringiensis Species 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 229940097012 bacillus thuringiensis Drugs 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 241000607720 Serratia Species 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 125000001246 bromo group Chemical group Br* 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- JFQOPBRQAVVLLX-UHFFFAOYSA-N BrC=1C=C(C(=NC=1)N1N=C2C(C=NC(=C2)C(F)(F)F)=C1)S(=O)(=O)CC Chemical compound BrC=1C=C(C(=NC=1)N1N=C2C(C=NC(=C2)C(F)(F)F)=C1)S(=O)(=O)CC JFQOPBRQAVVLLX-UHFFFAOYSA-N 0.000 description 13
- 229920000742 Cotton Polymers 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 241000244206 Nematoda Species 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 12
- 206010061217 Infestation Diseases 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
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- 239000007864 aqueous solution Substances 0.000 description 10
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- 230000009036 growth inhibition Effects 0.000 description 10
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 10
- 239000003016 pheromone Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
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- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- XBRCDWHXULVEFB-UHFFFAOYSA-N triphenyltin(1+) Chemical compound C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 XBRCDWHXULVEFB-UHFFFAOYSA-N 0.000 description 1
- NRHFWOJROOQKBK-UHFFFAOYSA-N triphenyltin;hydrate Chemical compound O.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 NRHFWOJROOQKBK-UHFFFAOYSA-N 0.000 description 1
- MLFGIRNMAOXTHS-UHFFFAOYSA-N tris(2-methylaziridin-1-yl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC1CN1P(=S)(N1C(C1)C)N1C(C)C1 MLFGIRNMAOXTHS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 241001515965 unidentified phage Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
- 229950006929 uredepa Drugs 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000011240 wet gel Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14180130 | 2014-08-07 | ||
| EP14180130.8 | 2014-08-07 | ||
| EP14186737 | 2014-09-29 | ||
| EP14186737.4 | 2014-09-29 | ||
| PCT/EP2015/067677 WO2016020286A1 (en) | 2014-08-07 | 2015-07-31 | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017523997A JP2017523997A (ja) | 2017-08-24 |
| JP2017523997A5 JP2017523997A5 (OSRAM) | 2018-09-06 |
| JP6685280B2 true JP6685280B2 (ja) | 2020-04-22 |
Family
ID=53773446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017506756A Active JP6685280B2 (ja) | 2014-08-07 | 2015-07-31 | 硫黄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 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9949483B2 (OSRAM) |
| EP (1) | EP3177620B1 (OSRAM) |
| JP (1) | JP6685280B2 (OSRAM) |
| CN (1) | CN106661023B (OSRAM) |
| BR (1) | BR112017002407B1 (OSRAM) |
| ES (1) | ES2701835T3 (OSRAM) |
| WO (1) | WO2016020286A1 (OSRAM) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI696612B (zh) | 2015-01-29 | 2020-06-21 | 日商日本農藥股份有限公司 | 具有環烷基吡啶基的稠合雜環化合物或其鹽類及含有該化合物的農園藝用殺蟲劑以及其使用方法 |
| CA2994604A1 (en) | 2015-08-07 | 2017-02-16 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents |
| PH12018500638B1 (en) | 2015-09-28 | 2022-06-03 | Bayer Cropscience Ag | 2-(het)aryl-substituted condensed bicyclic heterocyclic derivatives as pest control agents |
| WO2017072039A1 (de) | 2015-10-26 | 2017-05-04 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| 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 |
| WO2017134066A1 (en) | 2016-02-05 | 2017-08-10 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| MY190739A (en) * | 2016-07-07 | 2022-05-12 | Sumitomo Chemical Co | Heterocyclic compound and harmful arthropod controlling agent containing same |
| CA3031139A1 (en) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
| KR102419244B1 (ko) | 2016-08-15 | 2022-07-08 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
| AU2017340690B2 (en) | 2016-10-06 | 2021-05-20 | Bayer Cropscience Aktiengesellschaft | 2-(Het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| US10961248B2 (en) | 2016-12-01 | 2021-03-30 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2018113900A1 (en) * | 2016-12-19 | 2018-06-28 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| EP3568395A1 (de) | 2017-01-10 | 2019-11-20 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| US11058115B2 (en) | 2017-01-10 | 2021-07-13 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| 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 |
| JP7309615B2 (ja) | 2017-05-02 | 2023-07-18 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する有害生物防除に活性な複素環式誘導体 |
| JP7267262B2 (ja) * | 2017-09-18 | 2023-05-01 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物活性な複素環式誘導体 |
| WO2019076778A1 (en) | 2017-10-16 | 2019-04-25 | Syngenta Participations Ag | HETEROCYCLIC DERIVATIVES HAVING PESTICIDAL ACTIVITY HAVING SUBSTITUENTS CONTAINING SULFUR AND SULFONIMIDAMIDES |
| CN115772120A (zh) * | 2017-12-25 | 2023-03-10 | 住友化学株式会社 | 杂环化合物和含有该杂环化合物的有害节肢动物防除剂 |
| EP3733667B1 (en) * | 2017-12-26 | 2024-06-12 | Sumitomo Chemical Company, Limited | Heterocyclic compounds and noxious arthropod control agent containing same |
| EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| ES2906077T3 (es) | 2018-02-21 | 2022-04-13 | Bayer Ag | Derivados de heterociclos bicíclicos condensados como pesticidas |
| WO2019229089A1 (en) | 2018-05-31 | 2019-12-05 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| KR102808245B1 (ko) | 2018-06-06 | 2025-05-14 | 신젠타 크롭 프로텍션 아게 | 설폭시민 함유 치환체를 갖는 살충 활성 헤테로사이클릭 유도체 |
| AU2019296166B2 (en) | 2018-06-26 | 2024-01-18 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| TW202035404A (zh) | 2018-10-24 | 2020-10-01 | 瑞士商先正達農作物保護公司 | 具有含亞碸亞胺的取代基之殺有害生物活性雜環衍生物 |
| WO2020161208A1 (en) * | 2019-02-06 | 2020-08-13 | Syngenta Crop Protection Ag | Herbicidal fused pyridazine compounds |
| WO2020161209A1 (en) * | 2019-02-06 | 2020-08-13 | Syngenta Crop Protection Ag | Herbicidal fused pyridazine compounds |
| WO2020173861A1 (de) | 2019-02-26 | 2020-09-03 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2020173860A1 (en) | 2019-02-26 | 2020-09-03 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
| 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 |
| AR118243A1 (es) * | 2019-03-07 | 2021-09-22 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
| CN110622963A (zh) * | 2019-09-30 | 2019-12-31 | 江苏七洲绿色化工股份有限公司 | 一种含有丙环唑和环唑醇的可乳化颗粒剂及其制备方法和应用 |
| CN110583640A (zh) * | 2019-09-30 | 2019-12-20 | 江苏七洲绿色化工股份有限公司 | 一种含有吡唑醚菌酯和苯醚甲环唑的可乳化颗粒剂及其制备方法和应用 |
| CN115715290A (zh) | 2020-04-21 | 2023-02-24 | 拜耳公司 | 作为农药的2-(杂)芳基取代的稠杂环衍生物 |
| 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 |
| CN116033828B (zh) | 2020-07-02 | 2025-05-16 | 拜耳公司 | 作为害虫防治剂的杂环衍生物 |
| AU2021334184A1 (en) | 2020-08-31 | 2023-03-16 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| US20230265102A1 (en) | 2020-09-02 | 2023-08-24 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| EP4337661A1 (de) | 2021-05-12 | 2024-03-20 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
| US20250145640A1 (en) | 2021-08-10 | 2025-05-08 | Syngenta Crop Protection Ag | 2,2-difluoro-5h-[1,3]dioxolo[4,5-f]isoindol-7-one derivatives as pesticides |
| AU2024235487A1 (en) | 2023-03-14 | 2025-09-25 | Syngenta Crop Protection Ag | Control of pests resistant to insecticides |
| WO2025026738A1 (en) | 2023-07-31 | 2025-02-06 | Bayer Aktiengesellschaft | 6-[5-(ethylsulfonyl)-1-methyl-1h-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7h-imidazo[4,5-c]pyridazine derivatives as pesticides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103261170B (zh) * | 2010-12-24 | 2016-08-24 | 住友化学株式会社 | 稠杂环化合物及其用于害虫防治的用途 |
| TWI589570B (zh) * | 2011-08-04 | 2017-07-01 | 住友化學股份有限公司 | 稠合雜環化合物及其在病蟲害防制上之用途 |
| WO2013106254A1 (en) * | 2012-01-11 | 2013-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| JP6168055B2 (ja) * | 2012-06-18 | 2017-07-26 | 住友化学株式会社 | 縮合複素環化合物 |
-
2015
- 2015-07-31 CN CN201580042339.0A patent/CN106661023B/zh active Active
- 2015-07-31 BR BR112017002407-1A patent/BR112017002407B1/pt active IP Right Grant
- 2015-07-31 ES ES15745199T patent/ES2701835T3/es active Active
- 2015-07-31 US US15/500,956 patent/US9949483B2/en active Active
- 2015-07-31 WO PCT/EP2015/067677 patent/WO2016020286A1/en not_active Ceased
- 2015-07-31 EP EP15745199.8A patent/EP3177620B1/en active Active
- 2015-07-31 JP JP2017506756A patent/JP6685280B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112017002407B1 (pt) | 2021-11-23 |
| EP3177620A1 (en) | 2017-06-14 |
| JP2017523997A (ja) | 2017-08-24 |
| BR112017002407A2 (pt) | 2018-06-26 |
| CN106661023B (zh) | 2019-05-28 |
| US9949483B2 (en) | 2018-04-24 |
| CN106661023A (zh) | 2017-05-10 |
| ES2701835T3 (es) | 2019-02-26 |
| WO2016020286A1 (en) | 2016-02-11 |
| EP3177620B1 (en) | 2018-09-26 |
| US20170215425A1 (en) | 2017-08-03 |
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