KR102629107B1 - 해충 방제제로서의 2-(헤트)아릴-치환된 융합 비사이클릭 헤테로사이클 유도체 - Google Patents
해충 방제제로서의 2-(헤트)아릴-치환된 융합 비사이클릭 헤테로사이클 유도체 Download PDFInfo
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- KR102629107B1 KR102629107B1 KR1020187010246A KR20187010246A KR102629107B1 KR 102629107 B1 KR102629107 B1 KR 102629107B1 KR 1020187010246 A KR1020187010246 A KR 1020187010246A KR 20187010246 A KR20187010246 A KR 20187010246A KR 102629107 B1 KR102629107 B1 KR 102629107B1
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 38
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 273
- 238000000034 method Methods 0.000 claims abstract description 100
- 238000002360 preparation method Methods 0.000 claims abstract description 59
- 241001465754 Metazoa Species 0.000 claims abstract description 52
- -1 /or Species 0.000 claims description 122
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 239000000575 pesticide Substances 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000004606 Fillers/Extenders Substances 0.000 claims description 8
- 239000003905 agrochemical Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 9
- 239000000642 acaricide Substances 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 118
- 241000196324 Embryophyta Species 0.000 description 94
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 89
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 76
- 239000002904 solvent Substances 0.000 description 66
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 46
- 229910052736 halogen Inorganic materials 0.000 description 44
- 150000002367 halogens Chemical class 0.000 description 44
- 241000894007 species Species 0.000 description 44
- 238000012360 testing method Methods 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 24
- 238000009472 formulation Methods 0.000 description 24
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 description 22
- 241000238876 Acari Species 0.000 description 20
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
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- 239000003112 inhibitor Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 17
- 230000007935 neutral effect Effects 0.000 description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 125000003282 alkyl amino group Chemical group 0.000 description 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 16
- 239000003995 emulsifying agent Substances 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- 241000244206 Nematoda Species 0.000 description 13
- 241000258242 Siphonaptera Species 0.000 description 13
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 13
- 125000005159 cyanoalkoxy group Chemical group 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000003085 diluting agent Substances 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
- 230000009261 transgenic effect Effects 0.000 description 12
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 11
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 11
- 230000001965 increasing effect Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 10
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 10
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 10
- 241000258924 Ctenocephalides felis Species 0.000 description 10
- 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
- 240000008042 Zea mays Species 0.000 description 10
- 125000005103 alkyl silyl group Chemical group 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 125000000262 haloalkenyl group Chemical group 0.000 description 10
- 125000000232 haloalkynyl group Chemical group 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 10
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 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
- 241000239223 Arachnida Species 0.000 description 9
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- 235000010469 Glycine max Nutrition 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 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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- 235000005822 corn Nutrition 0.000 description 9
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 244000045947 parasite Species 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
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- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 8
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 8
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 description 8
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 description 8
- 241000193388 Bacillus thuringiensis Species 0.000 description 8
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 241000700605 Viruses Species 0.000 description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
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- 239000000975 dye Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 8
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- 238000004519 manufacturing process Methods 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
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- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 description 7
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- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 7
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- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 7
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
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- 150000003839 salts Chemical class 0.000 description 7
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- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- 241000282414 Homo sapiens Species 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 241000256251 Spodoptera frugiperda Species 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 description 6
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- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 6
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- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 6
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- 229920002554 vinyl polymer Polymers 0.000 description 1
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- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- PQHXFGUTAAIHOC-XZZSYSLUSA-N α-(methoxyimino)-n-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1\C=N\OC(C)C1=CC=CC(C(F)(F)F)=C1 PQHXFGUTAAIHOC-XZZSYSLUSA-N 0.000 description 1
Classifications
-
- 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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| ES2786573T3 (es) * | 2016-01-11 | 2020-10-13 | Bayer Cropscience Ag | Derivados de heterociclos como pesticidas |
| MX2019001918A (es) | 2016-08-15 | 2019-09-06 | Bayer Cropscience Ag | Derivados del heterociclo biciclico condensado como agentes de control de plagas. |
| 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 |
| WO2019013273A1 (ja) * | 2017-07-13 | 2019-01-17 | 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 |
| EP3733672B1 (en) | 2017-12-25 | 2023-03-22 | Sumitomo Chemical Company, Limited | Heterocyclic compounds and noxious arthropod control agent containing same |
| CN111770923B (zh) | 2017-12-26 | 2024-04-09 | 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 |
| JP7337810B2 (ja) * | 2018-01-15 | 2023-09-04 | 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的に活性な複素環式誘導体 |
| KR20200122353A (ko) | 2018-02-21 | 2020-10-27 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로시클릭 유도체 |
| ES2980209T3 (es) | 2018-06-26 | 2024-09-30 | Bayer Ag | Derivados heterocíclicos como plaguicidas |
| JP7399589B2 (ja) * | 2018-09-12 | 2023-12-18 | 日本化薬株式会社 | 有害生物防除剤 |
| WO2021009311A1 (en) | 2019-07-17 | 2021-01-21 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| WO2021033141A1 (en) | 2019-08-20 | 2021-02-25 | Pi Industries Ltd. | Fused heterocyclic compounds and their use as pest control agents |
| 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 |
| AR121344A1 (es) * | 2020-02-18 | 2022-05-11 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes para el control de plagas |
| WO2021213978A1 (de) | 2020-04-21 | 2021-10-28 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
| 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 |
| TW202311258A (zh) | 2021-05-12 | 2023-03-16 | 德商拜耳廠股份有限公司 | 作為除蟲劑之經2-(雜)芳基取代之稠合雜環衍生物 |
| WO2023041422A1 (en) | 2021-09-20 | 2023-03-23 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
| AU2024235487A1 (en) | 2023-03-14 | 2025-09-25 | Syngenta Crop Protection Ag | Control of pests resistant to insecticides |
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| WO2015000715A1 (en) | 2013-07-02 | 2015-01-08 | Syngenta Participations Ag | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
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| WO2013191113A1 (ja) | 2012-06-18 | 2013-12-27 | 住友化学株式会社 | 縮合複素環化合物 |
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| WO2014148451A1 (ja) | 2013-03-19 | 2014-09-25 | 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 |
| BR112015032689B1 (pt) | 2013-07-01 | 2020-03-10 | Sumitomo Chemical Company, Limited | Composto heterocíclico fundido, agente de controle de pragas e método para controlar pragas |
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| WO2015198859A1 (ja) | 2014-06-26 | 2015-12-30 | 住友化学株式会社 | 縮合複素環化合物 |
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| EP3177620B1 (en) | 2014-08-07 | 2018-09-26 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| WO2016023954A2 (en) | 2014-08-12 | 2016-02-18 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
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2016
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- 2016-09-23 CA CA2999790A patent/CA2999790A1/en not_active Abandoned
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| JP2013521237A (ja) | 2010-03-02 | 2013-06-10 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｃ型肝炎ウィルスｎｓ５ｂポリメラーゼの阻害薬 |
| WO2015000715A1 (en) | 2013-07-02 | 2015-01-08 | Syngenta Participations Ag | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
| WO2015121136A1 (de) | 2014-02-17 | 2015-08-20 | Bayer Cropscience Ag | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
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| CN108290886B (zh) | 2020-11-03 |
| TW201726672A (zh) | 2017-08-01 |
| AU2016330299B2 (en) | 2020-04-30 |
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| RU2018116054A (ru) | 2019-10-28 |
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| UY36918A (es) | 2017-04-28 |
| PH12018500638A1 (en) | 2018-10-01 |
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| AU2016330299A1 (en) | 2018-04-12 |
| JP6871917B2 (ja) | 2021-05-19 |
| EP3356362B1 (de) | 2021-02-03 |
| US10745398B2 (en) | 2020-08-18 |
| CA2999790A1 (en) | 2017-04-06 |
| CN108290886A (zh) | 2018-07-17 |
| JP2018529702A (ja) | 2018-10-11 |
| IL258089A (en) | 2018-05-31 |
| BR112018006198B1 (pt) | 2022-05-31 |
| WO2017055185A1 (de) | 2017-04-06 |
| BR112018006198A2 (pt) | 2018-10-09 |
| KR20180054680A (ko) | 2018-05-24 |
| CO2018003427A2 (es) | 2018-06-12 |
| ZA201802797B (en) | 2020-01-29 |
| EP3356362A1 (de) | 2018-08-08 |
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