ES2866911T3 - Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas - Google Patents
Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas Download PDFInfo
- Publication number
- ES2866911T3 ES2866911T3 ES16770499T ES16770499T ES2866911T3 ES 2866911 T3 ES2866911 T3 ES 2866911T3 ES 16770499 T ES16770499 T ES 16770499T ES 16770499 T ES16770499 T ES 16770499T ES 2866911 T3 ES2866911 T3 ES 2866911T3
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- ES
- Spain
- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- spp
- alkylsulfinyl
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 27
- 239000000575 pesticide Substances 0.000 title description 31
- -1 (C2-C6) cyanoalkenyl Chemical group 0.000 claims abstract description 238
- 150000001875 compounds Chemical class 0.000 claims abstract description 208
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 172
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 143
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 105
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 86
- 150000002367 halogens Chemical group 0.000 claims abstract description 81
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 66
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims abstract description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 40
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 39
- 125000001424 substituent group Chemical group 0.000 claims abstract description 39
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 38
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 33
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 33
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract description 33
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 32
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims abstract description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 27
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims abstract description 26
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 23
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims abstract description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 19
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims abstract description 19
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 18
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims abstract description 18
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 14
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims abstract description 14
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 13
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 13
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 12
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 11
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims abstract description 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 10
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims abstract description 10
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract description 8
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims abstract description 8
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims abstract description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 8
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 58
- 125000003282 alkyl amino group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 51
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 49
- 241001465754 Metazoa Species 0.000 claims description 48
- 125000004414 alkyl thio group Chemical group 0.000 claims description 44
- 241000607479 Yersinia pestis Species 0.000 claims description 36
- 238000009472 formulation Methods 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 29
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 29
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 26
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 22
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 22
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 21
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 239000011737 fluorine Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 11
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000003905 agrochemical Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 6
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 6
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 4
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 claims description 4
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 abstract description 7
- 241000196324 Embryophyta Species 0.000 description 88
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000002904 solvent Substances 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000011575 calcium Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000003112 inhibitor Substances 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 230000007935 neutral effect Effects 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000008199 coating composition Substances 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 150000003839 salts 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 239000002917 insecticide Substances 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
- 241000255925 Diptera Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 239000002270 dispersing agent Substances 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- 239000000546 pharmaceutical excipient Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000239223 Arachnida Species 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 238000000576 coating method Methods 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 239000013598 vector Substances 0.000 description 9
- 241000193388 Bacillus thuringiensis Species 0.000 description 8
- 240000002791 Brassica napus Species 0.000 description 8
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- 244000045947 parasite Species 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 7
- 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
- 241000238876 Acari Species 0.000 description 7
- 239000005799 Isopyrazam Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 239000000642 acaricide Substances 0.000 description 7
- 230000009471 action Effects 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 229940097012 bacillus thuringiensis Drugs 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 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 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000238421 Arthropoda Species 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 244000299507 Gossypium hirsutum 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
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 150000001543 aryl boronic acids Chemical class 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
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- 239000013008 thixotropic agent Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 206010044325 trachoma Diseases 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
- 229950001807 tribromsalan Drugs 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 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
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 201000010044 viral meningitis Diseases 0.000 description 1
- 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
- 229960004740 voriconazole Drugs 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15187145 | 2015-09-28 | ||
| PCT/EP2016/072697 WO2017055185A1 (de) | 2015-09-28 | 2016-09-23 | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2866911T3 true ES2866911T3 (es) | 2021-10-20 |
Family
ID=54207414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16770499T Active ES2866911T3 (es) | 2015-09-28 | 2016-09-23 | Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10745398B2 (OSRAM) |
| EP (1) | EP3356362B1 (OSRAM) |
| JP (1) | JP6871917B2 (OSRAM) |
| KR (1) | KR102629107B1 (OSRAM) |
| CN (1) | CN108290886B (OSRAM) |
| AR (1) | AR106165A1 (OSRAM) |
| AU (1) | AU2016330299B2 (OSRAM) |
| BR (1) | BR112018006198B1 (OSRAM) |
| CA (1) | CA2999790A1 (OSRAM) |
| CL (1) | CL2018000741A1 (OSRAM) |
| CO (1) | CO2018003427A2 (OSRAM) |
| ES (1) | ES2866911T3 (OSRAM) |
| IL (1) | IL258089A (OSRAM) |
| MX (1) | MX2018003761A (OSRAM) |
| PE (1) | PE20181094A1 (OSRAM) |
| PH (1) | PH12018500638B1 (OSRAM) |
| RU (1) | RU2018116054A (OSRAM) |
| TW (1) | TWI720023B (OSRAM) |
| UY (1) | UY36918A (OSRAM) |
| WO (1) | WO2017055185A1 (OSRAM) |
| ZA (1) | ZA201802797B (OSRAM) |
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| BR112018002180A2 (pt) * | 2015-10-13 | 2018-09-18 | Nihon Nohyaku Co., Ltd. | composto heterocíclico condensado contendo grupo oxima ou sal deste, inseticida agrícola e hortícola compreendendo o composto e método para usar o inseticida |
| 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 |
| CN109996799B (zh) | 2016-08-15 | 2022-07-19 | 拜耳作物科学股份公司 | 作为害虫防治剂的稠合双环杂环衍生物 |
| TW201833107A (zh) * | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物 |
| TWI762568B (zh) | 2017-02-06 | 2022-05-01 | 德商拜耳作物科學股份有限公司 | 製備鹵化咪唑並吡啶衍生物之方法 |
| EP3653624B1 (en) * | 2017-07-13 | 2022-12-07 | Sumitomo Chemical Company, Limited | Heterocyclic compound and harmful-arthropod control agent containing same |
| EP3733672B1 (en) | 2017-12-25 | 2023-03-22 | Sumitomo Chemical Company, Limited | Heterocyclic compounds and noxious arthropod control agent containing same |
| JP7274424B2 (ja) | 2017-12-26 | 2023-05-16 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
| CN111836810B (zh) * | 2018-01-15 | 2024-06-25 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
| EP3755700B1 (de) | 2018-02-21 | 2021-11-24 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| AU2019296166B2 (en) * | 2018-06-26 | 2024-01-18 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| 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 |
| AR120074A1 (es) | 2019-08-20 | 2022-02-02 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
| 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 |
| TW202200570A (zh) * | 2020-04-21 | 2022-01-01 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２—（雜）芳基取代的稠合雜環衍生物 |
| CN116940236A (zh) * | 2021-02-07 | 2023-10-24 | 山东康乔生物科技有限公司 | 含有苄胺类杀螨剂的组合物及其应用 |
| KR20240007207A (ko) | 2021-05-12 | 2024-01-16 | 바이엘 악티엔게젤샤프트 | 살충제로서의 2-(헤트)아릴-치환된 융합된 헤테로사이클 유도체 |
| EP4405348A1 (en) | 2021-09-20 | 2024-07-31 | 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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| US8273764B2 (en) | 2009-04-28 | 2012-09-25 | Sumitomo Chemical Company, Limited | Fused heterocyclic compounds and use thereof |
| AR080433A1 (es) * | 2010-03-02 | 2012-04-11 | Merck Sharp & Dohme | Derivados de benzofurancarboxamidas utiles para tratar o prevenir infecciones por vhc y composiciones farmaceuticas que los contienen. |
| TW201242962A (en) | 2010-12-01 | 2012-11-01 | Sumitomo Chemical Co | Pyrimidine compound and use for pest control thereof |
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| TWI545119B (zh) * | 2011-08-04 | 2016-08-11 | 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 |
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-
2016
- 2016-09-23 WO PCT/EP2016/072697 patent/WO2017055185A1/de not_active Ceased
- 2016-09-23 BR BR112018006198-0A patent/BR112018006198B1/pt active IP Right Grant
- 2016-09-23 MX MX2018003761A patent/MX2018003761A/es unknown
- 2016-09-23 JP JP2018515805A patent/JP6871917B2/ja active Active
- 2016-09-23 US US15/763,168 patent/US10745398B2/en active Active
- 2016-09-23 CA CA2999790A patent/CA2999790A1/en not_active Abandoned
- 2016-09-23 CN CN201680069088.XA patent/CN108290886B/zh active Active
- 2016-09-23 ES ES16770499T patent/ES2866911T3/es active Active
- 2016-09-23 AU AU2016330299A patent/AU2016330299B2/en not_active Ceased
- 2016-09-23 KR KR1020187010246A patent/KR102629107B1/ko active Active
- 2016-09-23 EP EP16770499.8A patent/EP3356362B1/de active Active
- 2016-09-23 PE PE2018000432A patent/PE20181094A1/es unknown
- 2016-09-23 RU RU2018116054A patent/RU2018116054A/ru not_active Application Discontinuation
- 2016-09-23 PH PH1/2018/500638A patent/PH12018500638B1/en unknown
- 2016-09-26 TW TW105130960A patent/TWI720023B/zh not_active IP Right Cessation
- 2016-09-26 UY UY0001036918A patent/UY36918A/es not_active Application Discontinuation
- 2016-09-27 AR ARP160102944A patent/AR106165A1/es unknown
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2018
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- 2018-03-21 CL CL2018000741A patent/CL2018000741A1/es unknown
- 2018-03-27 CO CONC2018/0003427A patent/CO2018003427A2/es unknown
- 2018-04-26 ZA ZA2018/02797A patent/ZA201802797B/en unknown
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|---|---|
| US20180303097A1 (en) | 2018-10-25 |
| TW201726672A (zh) | 2017-08-01 |
| PH12018500638B1 (en) | 2022-06-03 |
| CL2018000741A1 (es) | 2019-04-26 |
| BR112018006198A2 (pt) | 2018-10-09 |
| AU2016330299A1 (en) | 2018-04-12 |
| EP3356362A1 (de) | 2018-08-08 |
| PE20181094A1 (es) | 2018-07-09 |
| CA2999790A1 (en) | 2017-04-06 |
| CN108290886A (zh) | 2018-07-17 |
| RU2018116054A (ru) | 2019-10-28 |
| JP6871917B2 (ja) | 2021-05-19 |
| UY36918A (es) | 2017-04-28 |
| IL258089A (en) | 2018-05-31 |
| AU2016330299B2 (en) | 2020-04-30 |
| AR106165A1 (es) | 2017-12-20 |
| TWI720023B (zh) | 2021-03-01 |
| BR112018006198B1 (pt) | 2022-05-31 |
| MX2018003761A (es) | 2018-07-06 |
| ZA201802797B (en) | 2020-01-29 |
| WO2017055185A1 (de) | 2017-04-06 |
| EP3356362B1 (de) | 2021-02-03 |
| US10745398B2 (en) | 2020-08-18 |
| KR20180054680A (ko) | 2018-05-24 |
| CO2018003427A2 (es) | 2018-06-12 |
| CN108290886B (zh) | 2020-11-03 |
| JP2018529702A (ja) | 2018-10-11 |
| PH12018500638A1 (en) | 2018-10-01 |
| KR102629107B1 (ko) | 2024-01-24 |
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