ES2912385T3 - Insecticidas mesoiónicos - Google Patents
Insecticidas mesoiónicos Download PDFInfo
- Publication number
- ES2912385T3 ES2912385T3 ES18729821T ES18729821T ES2912385T3 ES 2912385 T3 ES2912385 T3 ES 2912385T3 ES 18729821 T ES18729821 T ES 18729821T ES 18729821 T ES18729821 T ES 18729821T ES 2912385 T3 ES2912385 T3 ES 2912385T3
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- 239000002917 insecticide Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 288
- -1 cyano, hydroxy, amino Chemical group 0.000 claims abstract description 144
- 125000001424 substituent group Chemical group 0.000 claims abstract description 65
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 23
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 19
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 17
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims abstract description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 14
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 5
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims abstract description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 4
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- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims abstract description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims abstract 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims abstract 3
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract 3
- 125000005109 alkynylthio group Chemical group 0.000 claims abstract 3
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims abstract 2
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- 238000000034 method Methods 0.000 claims description 78
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 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 17
- 125000004429 atom Chemical group 0.000 claims description 16
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 16
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000005660 Abamectin Substances 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 11
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- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
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- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 9
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 7
- 239000005897 Etoxazole Substances 0.000 claims description 7
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- 229950008167 abamectin Drugs 0.000 claims description 7
- 229960002587 amitraz Drugs 0.000 claims description 7
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 7
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 7
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 7
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 claims description 7
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims description 6
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 6
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims description 6
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 claims description 6
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 6
- 239000005875 Acetamiprid Substances 0.000 claims description 6
- 239000005878 Azadirachtin Substances 0.000 claims description 6
- 239000005874 Bifenthrin Substances 0.000 claims description 6
- 239000005885 Buprofezin Substances 0.000 claims description 6
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 6
- 239000005944 Chlorpyrifos Substances 0.000 claims description 6
- 239000005946 Cypermethrin Substances 0.000 claims description 6
- 239000005891 Cyromazine Substances 0.000 claims description 6
- 239000005892 Deltamethrin Substances 0.000 claims description 6
- 239000005894 Emamectin Substances 0.000 claims description 6
- 239000005895 Esfenvalerate Substances 0.000 claims description 6
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- 239000005899 Fipronil Substances 0.000 claims description 6
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- 239000005906 Imidacloprid Substances 0.000 claims description 6
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- 239000005925 Pymetrozine Substances 0.000 claims description 6
- 239000005926 Pyridalyl Substances 0.000 claims description 6
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- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 claims description 6
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- 241000700605 Viruses Species 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims description 6
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims description 6
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 claims description 6
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 6
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims description 6
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 claims description 6
- 229960001591 cyfluthrin Drugs 0.000 claims description 6
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 6
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 6
- 229960005424 cypermethrin Drugs 0.000 claims description 6
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 6
- 229950000775 cyromazine Drugs 0.000 claims description 6
- 229960002483 decamethrin Drugs 0.000 claims description 6
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 6
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 claims description 6
- 229950006824 dieldrin Drugs 0.000 claims description 6
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 claims description 6
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 6
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 claims description 6
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 6
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 6
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 6
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- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 claims description 6
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 6
- 229940056881 imidacloprid Drugs 0.000 claims description 6
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 6
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 claims description 6
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 6
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- 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
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000004235 valence bond calculation Methods 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin 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-IMTORBKUSA-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
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000000006 viral plant pathogen Species 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
- A01N43/90—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
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762503369P | 2017-05-09 | 2017-05-09 | |
| US201762548489P | 2017-08-22 | 2017-08-22 | |
| PCT/US2018/031097 WO2018208595A1 (en) | 2017-05-09 | 2018-05-04 | Mesoionic insecticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2912385T3 true ES2912385T3 (es) | 2022-05-25 |
Family
ID=62555159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES18729821T Active ES2912385T3 (es) | 2017-05-09 | 2018-05-04 | Insecticidas mesoiónicos |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11044910B2 (enExample) |
| EP (1) | EP3621964B1 (enExample) |
| JP (1) | JP7244441B2 (enExample) |
| KR (1) | KR102604099B1 (enExample) |
| CN (1) | CN110869370B (enExample) |
| BR (1) | BR112019023474B1 (enExample) |
| ES (1) | ES2912385T3 (enExample) |
| MX (1) | MX2019013133A (enExample) |
| WO (1) | WO2018208595A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018108730A1 (de) * | 2016-12-16 | 2018-06-21 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
| JP2020517624A (ja) * | 2017-04-21 | 2020-06-18 | バイエル・アクチエンゲゼルシヤフト | 殺虫剤としてのメソイオン性イミダゾピリジン類 |
| EP3975718A1 (en) * | 2019-05-29 | 2022-04-06 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| CN113907084A (zh) * | 2021-11-30 | 2022-01-11 | 江苏钟山新材料有限公司 | 一种二氯噻吡嘧啶·烯啶虫胺油悬浮剂及其制备方法和应用 |
| WO2024071393A1 (ja) * | 2022-09-30 | 2024-04-04 | 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組成物 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DE69033861T2 (de) | 1989-08-30 | 2002-06-06 | Kynoch Agrochemicals (Proprietary) Ltd., Sandton | Herstellung eines Dosierungsmittels |
| CA2083185A1 (en) | 1990-03-12 | 1991-09-13 | William Lawrence Geigle | Water-dispersible or water-soluble pesticide granules from heat-activated binders |
| ES2091878T3 (es) | 1990-10-11 | 1996-11-16 | Sumitomo Chemical Co | Composicion plaguicida. |
| US6406690B1 (en) | 1995-04-17 | 2002-06-18 | Minrav Industries Ltd. | Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| TWI401023B (zh) * | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| TWI482771B (zh) * | 2009-05-04 | 2015-05-01 | Du Pont | 磺醯胺殺線蟲劑 |
| UA110924C2 (uk) * | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| CN102574815A (zh) * | 2009-08-05 | 2012-07-11 | 杜邦公司 | 介离子杀虫剂 |
| KR20120050467A (ko) * | 2009-08-05 | 2012-05-18 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 메소이온성 살충제 |
| UA107804C2 (en) * | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| TWI528899B (zh) * | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| MX2018006749A (es) * | 2015-12-03 | 2018-08-15 | Bayer Cropscience Ag | Derivados de 3-(acetil)-1-[(1,3-tiazol-5-il)metil]-1h-imidazo[1,2- a]piridin-4-io-2-olato halogenados mesoionicos y compuestos relacionados como insecticidas. |
| WO2018108730A1 (de) * | 2016-12-16 | 2018-06-21 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
| EP3609887A1 (de) * | 2017-04-12 | 2020-02-19 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
| BR112019025331A2 (pt) * | 2017-06-16 | 2020-06-23 | Basf Se | Compostos da fórmula (i), composição, métodos de proteção de safras e de combate, método não terapêutico de tratamento, semente, uso dos compostos e uso de composto |
| WO2019086474A1 (en) * | 2017-10-31 | 2019-05-09 | Syngenta Participations Ag | Pesticidally active mesoionics heterocyclic compounds |
| EP3636644A1 (de) * | 2018-10-11 | 2020-04-15 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
-
2018
- 2018-05-04 BR BR112019023474-8A patent/BR112019023474B1/pt active IP Right Grant
- 2018-05-04 ES ES18729821T patent/ES2912385T3/es active Active
- 2018-05-04 CN CN201880045654.2A patent/CN110869370B/zh active Active
- 2018-05-04 MX MX2019013133A patent/MX2019013133A/es unknown
- 2018-05-04 JP JP2019561815A patent/JP7244441B2/ja active Active
- 2018-05-04 KR KR1020197036153A patent/KR102604099B1/ko active Active
- 2018-05-04 EP EP18729821.1A patent/EP3621964B1/en active Active
- 2018-05-04 WO PCT/US2018/031097 patent/WO2018208595A1/en not_active Ceased
- 2018-05-04 US US16/612,097 patent/US11044910B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20200093133A1 (en) | 2020-03-26 |
| BR112019023474B1 (pt) | 2023-12-19 |
| US11044910B2 (en) | 2021-06-29 |
| EP3621964A1 (en) | 2020-03-18 |
| CN110869370A (zh) | 2020-03-06 |
| EP3621964B1 (en) | 2022-03-02 |
| JP2020519603A (ja) | 2020-07-02 |
| MX2019013133A (es) | 2020-02-05 |
| CN110869370B (zh) | 2023-04-11 |
| WO2018208595A1 (en) | 2018-11-15 |
| JP7244441B2 (ja) | 2023-03-22 |
| BR112019023474A2 (pt) | 2020-06-30 |
| KR102604099B1 (ko) | 2023-11-22 |
| KR20200004385A (ko) | 2020-01-13 |
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