CN109516996B - 一种大环内酯类衍生物、其合成及应用 - Google Patents
一种大环内酯类衍生物、其合成及应用 Download PDFInfo
- Publication number
- CN109516996B CN109516996B CN201811413890.3A CN201811413890A CN109516996B CN 109516996 B CN109516996 B CN 109516996B CN 201811413890 A CN201811413890 A CN 201811413890A CN 109516996 B CN109516996 B CN 109516996B
- Authority
- CN
- China
- Prior art keywords
- compound
- dmso
- nmr
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 36
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 7
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 230000012010 growth Effects 0.000 claims abstract description 9
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 fenhexatin Chemical compound 0.000 claims description 32
- 239000005660 Abamectin Substances 0.000 claims description 11
- 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 10
- 229950008167 abamectin Drugs 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229940126062 Compound A Drugs 0.000 claims description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 8
- 239000005663 Pyridaben Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 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 8
- 241000244206 Nematoda Species 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 4
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d 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(O[C@@H]([C@@H](C)CC4)C(C)C)O3)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.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 4
- 241000239223 Arachnida Species 0.000 claims description 4
- 241000254173 Coleoptera Species 0.000 claims description 4
- 241000255925 Diptera Species 0.000 claims description 4
- 241000237858 Gastropoda Species 0.000 claims description 4
- 241000258937 Hemiptera Species 0.000 claims description 4
- 241001466007 Heteroptera Species 0.000 claims description 4
- 241000257303 Hymenoptera Species 0.000 claims description 4
- 241001495069 Ischnocera Species 0.000 claims description 4
- 241000256602 Isoptera Species 0.000 claims description 4
- 241000255777 Lepidoptera Species 0.000 claims description 4
- 241000238814 Orthoptera Species 0.000 claims description 4
- 241001674048 Phthiraptera Species 0.000 claims description 4
- 241001415024 Psocoptera Species 0.000 claims description 4
- 241000258242 Siphonaptera Species 0.000 claims description 4
- 239000005937 Tebufenozide Substances 0.000 claims description 4
- 241001414989 Thysanoptera Species 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound 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](NC)[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 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 claims description 4
- 229960002418 ivermectin Drugs 0.000 claims description 4
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims description 4
- 241000237519 Bivalvia Species 0.000 claims description 3
- 239000005657 Fenpyroximate Substances 0.000 claims description 3
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 3
- 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 3
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 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 2
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 claims description 2
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 claims description 2
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 2
- HVQHXBNMBZJPLK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methylprop-2-en-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound CC(=C)CNC1=C([S+]([O-])C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HVQHXBNMBZJPLK-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 239000005875 Acetamiprid Substances 0.000 claims description 2
- 239000005878 Azadirachtin Substances 0.000 claims description 2
- 239000005874 Bifenthrin Substances 0.000 claims description 2
- 239000005886 Chlorantraniliprole Substances 0.000 claims description 2
- 239000005888 Clothianidin Substances 0.000 claims description 2
- 239000005891 Cyromazine Substances 0.000 claims description 2
- 239000005893 Diflubenzuron Substances 0.000 claims description 2
- 239000005900 Flonicamid Substances 0.000 claims description 2
- 239000005780 Fluazinam Substances 0.000 claims description 2
- 239000005959 Fosthiazate Substances 0.000 claims description 2
- 239000005661 Hexythiazox Substances 0.000 claims description 2
- 239000005906 Imidacloprid Substances 0.000 claims description 2
- 239000005907 Indoxacarb Substances 0.000 claims description 2
- 239000005912 Lufenuron Substances 0.000 claims description 2
- 239000005914 Metaflumizone Substances 0.000 claims description 2
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 claims description 2
- 239000005918 Milbemectin Substances 0.000 claims description 2
- 239000005924 Pirimiphos-methyl Substances 0.000 claims description 2
- 239000005925 Pymetrozine Substances 0.000 claims description 2
- 239000005927 Pyriproxyfen Substances 0.000 claims description 2
- 239000005930 Spinosad Substances 0.000 claims description 2
- 239000005664 Spirodiclofen Substances 0.000 claims description 2
- 239000005931 Spirotetramat Substances 0.000 claims description 2
- 239000005934 Sulfoxaflor Substances 0.000 claims description 2
- 239000005940 Thiacloprid Substances 0.000 claims description 2
- 239000005941 Thiamethoxam Substances 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- FVECELJHCSPHKY-WTFKENEKSA-N Veratrine (amorphous) Chemical compound 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 FVECELJHCSPHKY-WTFKENEKSA-N 0.000 claims description 2
- TUEIURIZJQRMQE-UHFFFAOYSA-N [2-(tert-butylsulfamoyl)phenyl]boronic acid Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=CC=C1B(O)O TUEIURIZJQRMQE-UHFFFAOYSA-N 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 claims description 2
- UWGBIKPRXRSRNM-UHFFFAOYSA-N cevadine Natural products CC=C(C)/C(=O)OC1CCC2(C)C3CCC4C5(O)CC(O)C6(O)C(CN7CC(C)CCC7C6(C)O)C5(O)CC24OCC13O UWGBIKPRXRSRNM-UHFFFAOYSA-N 0.000 claims description 2
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 claims description 2
- 229960001591 cyfluthrin Drugs 0.000 claims description 2
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 2
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 2
- 229950000775 cyromazine Drugs 0.000 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 claims description 2
- 229940019503 diflubenzuron Drugs 0.000 claims description 2
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 2
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims description 2
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 2
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 claims description 2
- HICUREFSAIZXFQ-JOWPUVSESA-N i9z29i000j Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\[C@H](OC(=O)C(=N/OC)\C=1C=CC=CC=1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 HICUREFSAIZXFQ-JOWPUVSESA-N 0.000 claims description 2
- 229940056881 imidacloprid Drugs 0.000 claims description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 2
- 229960000521 lufenuron Drugs 0.000 claims description 2
- 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 2
- 229930002897 methoprene Natural products 0.000 claims description 2
- 229950003442 methoprene Drugs 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229940079888 nitenpyram Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 claims description 2
- 229950001664 phoxim Drugs 0.000 claims description 2
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 claims description 2
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 2
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 2
- YYXSCUSVVALMNW-FOWTUZBSSA-N pyriminostrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 YYXSCUSVVALMNW-FOWTUZBSSA-N 0.000 claims description 2
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims description 2
- 229940080817 rotenone Drugs 0.000 claims description 2
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 claims description 2
- 229940014213 spinosad Drugs 0.000 claims description 2
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 claims description 2
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 239000001119 stannous chloride Substances 0.000 claims description 2
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 claims description 2
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 2
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims description 2
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 claims description 2
- 239000005898 Fenoxycarb Substances 0.000 claims 2
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 claims 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 claims 1
- MMCJEAKINANSOL-UHFFFAOYSA-N Methiuron Chemical compound CN(C)C(=S)NC1=CC=CC(C)=C1 MMCJEAKINANSOL-UHFFFAOYSA-N 0.000 claims 1
- 239000005942 Triflumuron Substances 0.000 claims 1
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 0.000 claims 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- FYQGBXGJFWXIPP-UHFFFAOYSA-N hydroprene Chemical compound CCOC(=O)C=C(C)C=CCC(C)CCCC(C)C FYQGBXGJFWXIPP-UHFFFAOYSA-N 0.000 claims 1
- 229930000073 hydroprene Natural products 0.000 claims 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 16
- 238000011161 development Methods 0.000 abstract description 6
- 241000233866 Fungi Species 0.000 abstract description 5
- 244000052616 bacterial pathogen Species 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 128
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- 230000000694 effects Effects 0.000 description 31
- 239000000375 suspending agent Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 13
- 230000001276 controlling effect Effects 0.000 description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 10
- 239000005783 Fluopyram Substances 0.000 description 7
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 description 7
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 6
- 229940126086 compound 21 Drugs 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 5
- 241000254127 Bemisia tabaci Species 0.000 description 5
- 241000255967 Helicoverpa zea Species 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241000594031 Liriomyza sativae Species 0.000 description 4
- 241000243785 Meloidogyne javanica Species 0.000 description 4
- 241000488581 Panonychus citri Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 4
- 229940125833 compound 23 Drugs 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- 241000223195 Fusarium graminearum Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- 231100000086 high toxicity Toxicity 0.000 description 3
- 230000028644 hyphal growth Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- 239000005894 Emamectin Substances 0.000 description 2
- 239000005916 Methomyl Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class 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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 229940125846 compound 25 Drugs 0.000 description 2
- 229940125851 compound 27 Drugs 0.000 description 2
- 229940127204 compound 29 Drugs 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin 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](C3CCCCC3)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 QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 description 2
- 229960003997 doramectin Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- WPNHOHPRXXCPRA-TVXIRPTOSA-N eprinomectin Chemical compound O1[C@@H](C)[C@@H](NC(C)=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 WPNHOHPRXXCPRA-TVXIRPTOSA-N 0.000 description 2
- 229960002346 eprinomectin Drugs 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006303 photolysis reaction Methods 0.000 description 2
- 230000015843 photosynthesis, light reaction Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 2
- 229960002245 selamectin Drugs 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- 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 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 239000005887 Chromafenozide Substances 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001494246 Daphnia magna Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 241000594036 Liriomyza Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005917 Methoxyfenozide Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 239000005926 Pyridalyl Substances 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 239000005929 Spinetoram Substances 0.000 description 1
- 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 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- RRZXIRBKKLTSOM-UHFFFAOYSA-N avermectin B1a Natural products C1=CC(C)C(C(C)CC)OC11OC(CC=C(C)C(OC2OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C2)C(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 RRZXIRBKKLTSOM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004497 emulsifiable granule Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 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 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种大环内酯类衍生物、其合成及应用,属于有机化合物开发和应用领域。本发明的大环内酯类衍生物结构如式(I)所示。本发明的大环内酯类衍生物光稳定性好,这一优势在农业上防治害虫具有非常大的优势。既可防治多种害虫,同时可以抑制真菌生长;兼有抑制病原菌和害虫生长的特性,对于有害生物防治,降低农药用量具有非常重要的现实意义。
Description
技术领域
本发明涉及有机化合物开发和应用领域,特别涉及一种大环内酯类衍生物、其合成及应用。
背景技术
高毒和对环境不安全的农药品种逐渐被各国政府禁用,对于农业病虫害的防治,亟需新农药的研发。但是近年来,新化合物的出现和登记却变的非常困难,这是因为新农药化合物筛选的成功率在下降,研发周期在延长,从而加大了研发成本。其原因主要是起点要求高,新品种必须在通过了活性和功能筛选程序后,还要通过生态环境筛选,以致成功率降低。
通过对具有活性的母体进行结构改造来获得活性更优、安全性更高的新品种,已经成为当今新农药创制的重要手段。并且已有很多成功的案例。
具有16元大环内酯结构的化合物是从土壤微生物-链霉菌的发酵物中提取而得到的,已被成功应用于农药和兽药等领域,带来了巨大的经济价值,为社会的健康发展做出了巨大的贡献。目前开发成杀虫剂比较成功的品种是阿维菌素和弥拜菌素,但它们还存在一些缺点,如:对高等动物的毒性比较高毒,对水生生物中的鱼类、大型溞、藻类、虾类和蟹类都是高毒,以及容易降解等缺点。研究者针对这两种化合物进行了大量的结构衍生研究(已有许多的研究型论文和专利报道),取得了许多突破性的进展。其中商品化的阿维菌素衍生物有伊维菌素(ivermectin)、埃玛菌素(emamectin)、道拉菌素(doramectin)、埃珀利诺菌素(eprinomectin)和色拉菌素(selamectin)等。派生的新化合物克服了阿维菌素的某些不足,在防治范围、杀虫活性和对人畜及环境毒性等方面有所改善,但这些新化合物光稳定性差,施用到植物叶面后容易降解,因而不能长期有效控制农业害虫。
发明内容
为了弥补现有技术的不足,本发明提供了一种大环内酯类衍生物、其合成及应用。
本发明的技术方案为:
一种大环内酯类衍生物,如式(Ⅰ)所示:
其中,
X-Y为CH2-CH2、CH=CH、CH2-CH-OR1或CH2-O;
R为氢、卤素、硝基、羟基、烷基或取代烷基、烷氧基或取代烷氧基、烷基羰基或取代烷基羰基、烷氧基羰基或取代烷氧基羰基、芳基或取代芳基中的任意一种;
其中,R3为烷基或取代烷基、烷氧基或取代烷氧基、烷基羰基或取代烷基羰基、烷氧基羰基或取代烷氧基羰基、芳基或取代芳基。
作为优选方案,所述芳基为单环芳香烃基、多环芳香烃基、稠环芳香烃基或芳杂环基。如苯基、萘基、蒽基、菲基、苊基、吡咯基、咪唑基、噻唑基、吡啶基、吡嗪基、吡唑基、吲哚基、喹啉基等等。
作为优选方案,所述取代烷基为卤素、氰基、硝基、羟基、磺酰基取代的烷基;所述取代芳基为卤素、烷基或取代烷基、烷氧基、氰基、硝基、羟基、磺酰基取代的芳基;所述取代烷氧基为烷氧基中任意一个或多个氢被卤素、氰基、硝基、羟基、磺酰基取代的烷氧基;所述取代烷基羰基为烷基羰基中任意一个或多个氢被卤素、氰基、硝基、羟基、磺酰基取代的烷基羰基;所述取代烷氧基羰基为烷氧基羰基中任意一个或多个氢被卤素、氰基、硝基、羟基、磺酰基取代的烷氧基羰基。
作为优选方案,所述烷基为C1~C8直链、支链或环状烷基(如甲基、乙基、正丙基、异丙基、丁基、正丁基、环戊基、环己基等等);所述烷氧基为C1~C6烷氧基(如甲氧基、乙氧基等等);所述烷基羰基为C1~C6的烷基羰基(如甲酰基、乙酰基、丙酰基、异丙酰基、丁酰基、异丁酰基、叔丁酰基等等);所述烷氧基羰基为C1~C6的烷氧基羰基(如甲氧羰基、乙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基、叔丁氧羰基等等)。
作为优选方案,所述芳杂环基为嘧啶基、吡唑基、噻吩基、噁唑基、异噻唑基。
所述大环内酯类衍生物的合成方法,将化合物A于10℃~100℃下溶解到溶剂中,加入催化剂,搅拌并通入氮气保护,滴加化合物B;反应完毕后,经纯化,得到式(Ⅰ)所述大环内酯类衍生物;
化合物A的通式为:
X-Y为CH2-CH2、CH=CH、CH2-CH-OH或CH2-O;
R为氢、卤素、硝基、羟基、烷基或取代烷基、烷氧基或取代烷氧基、烷基羰基或取代烷基羰基、烷氧基羰基或取代烷氧基羰基、芳基或取代芳基中的任意一种;
R’为-OH或
化合物B的结构为:O=C=N-R3或S=C=N-R3。
其中,R3为烷基或取代烷基、烷氧基或取代烷氧基、烷基羰基或取代烷基羰基、烷氧基羰基或取代烷氧基羰基、芳基或取代芳基。
作为优选方案,所述化合物A与化合物B的摩尔比为1:0.5~1:10;催化剂为氯化亚锡、四丁基锡、醋酸三丁基锡、三氯正丁基锡、三甲基锡氢氧化物、二氯二甲基锡、二月桂酸二丁基锡中的任意一种。
更优选的,所述化合物A与化合物B的摩尔比为1:1~1:3;化合物A与催化剂的摩尔比为1:0.05~1:0.2。
所述溶剂为苯、甲苯、二甲苯、二氯甲烷、戊烷、己烷、环己烷、环己酮、丙酮、乙腈中的一种或几种。
所述大环内酯类衍生物在防治害虫中的用途;所述害虫包括蛛形纲、双壳纲、腹足纲、线虫纲、唇足目、弹尾目、虱目、双翅目、鞘翅目、直翅目、异翅亚目、同翅目、膜翅目、等翅目、鳞翅目、食毛目、啮虫目、蚤目、缨翅目、缨尾目、植物寄生线虫。
所述大环内酯类衍生物在抑制真菌生长中的用途。
所述大环内酯类衍生物与成分C的混合物在防治害虫中的用途;所述害虫包括蛛形纲、双壳纲、腹足纲、线虫纲、唇足目、弹尾目、虱目、双翅目、鞘翅目、直翅目、异翅亚目、同翅目、膜翅目、等翅目、鳞翅目、食毛目、啮虫目、蚤目、缨翅目、缨尾目、植物寄生线虫;所述成分C选自哒螨灵、稻瘟灵、氰氟虫腙、杀螨素、苯螨特、溴螨酯、三氯杀螨醇、三氯杀螨砜、噻螨酮、***锡、三环锡、苯丁锡、炔螨特、苯氟磺胺、唑螨酯、嘧螨胺、阿维菌素、甲氨基阿维菌素苯甲酸盐、伊维菌素、雷皮菌素、弥拜菌素、多杀菌素、乙基多杀菌素、苏云金素、印楝素、鱼藤酮、藜芦碱、杀螟丹、杀虫环、杀虫单、杀虫双、氟吡菌酰胺、氯虫酰胺、氯虫苯甲酰胺、溴氰虫酰胺、虫脲、噻嗪酮、氟啶脲、氟啶胺、灭蝇胺、环虫腈、除虫脲、氟螨脲、氟虫脲、氟铃脲、虱螨脲、氟酰脲、氟幼脲、氟苯脲、杀铃脲、灭幼脲、苯氧威、烯虫乙酯、烯虫酯炔、烯虫酯、吡丙醚、啶虫丙醚、环虫酰肼、氯虫酰肼、甲氧虫酰肼、虫酰肼、呋喃虫酰肼、氟啶虫酰胺、噻虫胺、噻虫嗪、噻虫啉、吡虫啉、啶虫脒、烯啶虫胺、呋虫胺、吡蚜酮、氟啶虫胺腈、哌虫胺、茚虫威、氟虫腈、丁烯氟虫腈、唑虫酰胺、溴虫腈、螺螨酯、螺虫乙酯、丁醚脲、联苯菊酯、氟氯氰菊酯、高效氯氟氰菊酯、高效氟氯氰菊酯、高效氯氰菊酯、氰戊菊酯、噁虫威、灭多威、杀线威、残杀威、毒死蜱、甲基毒死蜱、二嗪磷、辛硫磷、甲基嘧啶磷、噻唑膦、杀朴磷中的一种或几种。
现已发现本发明所述大环内酯类衍生物与成分C的混合物,具有协同活性,并可用于防治有害生物,这不但扩大了本发明所述大环内酯类衍生物和成分C的作用范围,而且也有助于降低农药用量,延缓有害生物的抗药性。其中本发明所述大环内酯类衍生物与成分C的重量比为1000:1至1:1000,其中优选100:1至1:80,更优选30:1至1:9。
本发明所述大环内酯类衍生物或者其与成分C的组合物可以用于防治(抑制或消灭)以上出现在农业、园艺、林业和卫生中的害虫。
本发明所述大环内酯类衍生物或者其与成分C的组合物的用量取决于防治对象和预期效果,通常用量范围为1-2000g活性成分/公顷。
本发明所述大环内酯类衍生物或者其与成分C的组合物可以制成任何剂型或者药物类型;例如可以制成种子处理干粉剂,种子处理乳剂,种子处理悬浮剂,种子处理液剂,种子处理可分散粉剂,种子处理微囊悬浮剂,种子处理凝胶,乳油,悬浮剂,悬乳剂,微囊悬浮剂,水分散粒剂,乳粒剂,水乳剂,微乳剂,油分散体,油悬浮剂,油剂,可溶液剂,超低容量液剂,超低容量微囊悬浮剂,母药,可分散液剂,可湿性粉剂或结合农业上可接受的助剂的任何技术上可行的制剂。通常,制剂含有0.01至90t%的活性成分,0-20%农业上可接受的表面活性剂和10-90%固体或液体制剂惰性物质和助剂。
本发明的有益效果为:
1、本发明所得新化合物,即,式(Ⅰ)所示的大环内酯类衍生物,光稳定性好,这一优势在农业上防治害虫具有非常大的优势。
2、本发明大环内酯类衍生物的合成方法操作简单,收率较高,合成成本低,适于产业化应用。
3、本发明所得式(Ⅰ)所示的大环内酯类衍生物既可防治多种害虫,同时可以抑制真菌生长;兼有抑制病原菌和害虫生长的特性,对于有害生物防治,降低农药用量具有非常重要的现实意义。
4、本发明所得式(Ⅰ)所示的大环内酯类衍生物与成分C的组合物,可降低农药用量,并可延缓有害生物的抗药性。
具体实施方式
衍生物制备实施例
在50℃条件下,将1.00mol化合物A溶解到二氯甲烷中,加入催化剂0.005mol,形成反应液;将反应液移至50℃温下搅拌反应,并通入氮气,按照化合物A与化合物B的摩尔比为1:3缓慢滴加化合物B,反应完成后,有机相经蒸馏、干燥、纯化后得到目标化合物。
各实施例中化合物A、化合物B以及生产的新的大环内酯类衍生物的结构如表1所示。
表1各实施例中反应物与产物结构汇总表
表1中各化合物A的结构式如下:
一、化合物结构或特性研究
1.1化合物结构测定谱数据:
化合物1:1H NMR(400MHz,DMSO-d6)δ8.97(d,J=34.7Hz,3H),8.23(s,1H),7.13(t,J=7.8Hz,1H),6.94(t,J=7.4Hz,9H),6.62-6.30(m,7H),5.60(d,J=4.7Hz,1H),5.37-5.23(s,1H),4.71(d,J=8.0Hz,1H),4.49(d,J=23.7Hz,2H),3.89(d,J=5.4Hz,1H),3.79(dd,J=18.9,7.4Hz,1H),2.11-1.87(m,2H),1.64-1.49(m,9H),1.18(d,J=9.2Hz,2H),1.11-0.97(m,2H),0.85(m,3H).13C NMR(126MHz,DMSO-d6)δ156.7,152.94,146.9,139.5,138.6,130.17,129.7,127.5,126.08,124.8,122.66,118.2,117.5,101.4,96.4,87.3,77.9,73.6,70.5,68.2,65.2,56.8,45.9,39.8,39.7,38.6,34.3,30.7,22.3,18.1,16.1,13.6,11.7.
化合物2:1H NMR(400MHz,DMSO-d6)δ10.01(s,1H),8.84(s,20H),7.51-7.44(m,31H),6.68-6.40(m,3H),5.64(dd,J=15.6,9.8Hz,1H),5.13(s,1H),4.72(d,J=16.5Hz,1H),4.09(d,J=14.5Hz,1H),3.89-3.79(m,1H),2.52-2.47(m,12H),2.20(d,J=7.8Hz,3H),1.52(dd,J=13.1,8.1Hz,1H),1.19(d,J=5.1Hz,2H),0.81(d,J=20.7Hz,5H).13C NMR(126MHz,DMSO-d6)δ158.2,149.2,139.5,131.51,128.3,119.5,113.36,101.5,95.6,77.6,70.9,68.5,67.1,57.8,56.4,45.6,39.3,30.5,29.4,21.5,19.8,16.5,15.2,13.5,11.8.
化合物3:1H NMR(400MHz,DMSO-d6)δ10.00(s,1H),8.84(s,24H),7.38-7.29(m,20H),6.52-6.20(m,3H),5.67-5.51(m,1H),4.42(s,2H),3.89(d,J=5.1Hz,1H),3.27-3.12(m,1H),2.50(p,J=1.9Hz,11H),2.21(s,3H),2.08(d,J=8.8Hz,1H),1.73(s,2H),1.41-1.25(m,1H),1.21(s,4H),1.18(d,J=6.0Hz,1H),0.96(dd,J=16.3,6.5Hz,2H),0.88(dt,J=20.7,7.1Hz,5H).13C NMR(126MHz,DMSO-d6)δ152.5,140.5,139.0,138.7,134.7,128.7,123.8,121.1,119.3,113.79,98.6,85.6,81.3,79.2,78.8,72.6,70.6,68.7,67.2,57.1,56.2,44.2,42.6,39.1,34.3,33.9,30.0,27.2,21.0,19.7,14.0,13.1,11.8.
化合物4:1H NMR(400MHz,DMSO-d6)δ9.76(s,1H),8.55(s,9H),7.28(d,J=8.1Hz,22H),6.62-6.26(m,9H),5.74-5.51(m,2H),5.39(d,J=5.1Hz,1H),5.14(t,J=7.7Hz,1H),4.79-4.45(m,1H),3.47-3.30(m,11H),2.64(dt,J=9.2,4.6Hz,1H),2.21(d,J=9.0Hz,5H),1.74(s,3H),1.41-1.30(m,1H),1.25(d,J=7.6Hz,1H),0.90(dt,J=19.8,7.7Hz,9H),0.80(d,J=11.7Hz,2H).13C NMR(126MHz,DMSO-d6)δ152.9,140.1,138.4,129.8,128.0,123.1,121.0,119.3,115.9,98.6,81.9,79.3,78.0,70.4,68.9,67.2,57.1,56.2,45.82,41.6,35.3,34.9,30.0,27.2,21.0,20.9,19.7,18.67,15.0,12.8.
化合物5:1H NMR(400MHz,DMSO-d6)δ8.68(s,13H),7.75-7.36(m,29H),7.21(t,J=9.7Hz,28H),6.61-6.20(m,2H),5.87-5.56(m,1H),4.77-4.34(m,2H),3.92-3.81(m,2H),3.25-3.03(m,9H),2.98-2.64(m,2H),1.76(s,3H),1.61-1.44(m,2H),0.92(d,J=15.6Hz,1H),0.81(d,J=21.1Hz,3H).13C NMR(126MHz,DMSO-d6)δ173.7,156.1,145.8,138.3,127.9,128.4,121.8,116.1,110.9,92.5,87.4,82.8,76.7,72.1,70.3,68.1,66.7,57.4,56.4,39.3,33.4,30.5,29.9,22.1,19.5,18.7,16.3,12.6,11.4.
化合物6:1H NMR(400MHz,DMSO-d6)δ11.05(s,2H),7.51(s,4H),7.18(d,J=8.1Hz,10H),6.59-6.34(m,6H),4.22-4.15(m,2H),3.63-3.50(m,2H),3.41(d,J=9.2Hz,12H),3.18-3.01(m,8H),2.82-2.60(s,1H),2.48-2.20(m,4H),2.13(dd,J=10.2,7.3Hz,1H),1.90-1.84(m,1H),1.44-1.25(m,1H),1.21(s,1H),1.19-1.07(m,6H),0.95(dd,J=20.36,9.5Hz,2H),0.80(d,J=12.1Hz,3H).13C NMR(126MHz,DMSO-d6)δ173.7,157.1,153.8,152.3,138.3,136.4,136.5,131.1,127.9,117.7,128.4,121.3,121.3,118.9,106.4,92.5,83.4,79.8,75.9,74.1,70.6,68.3,67.9,57.4,45.6,39.9,34.2,29.9,28.2,20.3,18.7,15.9,13.2,11.9.
化合物7:1H NMR(400MHz,DMSO-d6)δ12.84(s,2H),7.92(s,12H),7.55(d,J=8.5Hz,16H),6.57-6.25(m,2H),5.79-5.42(m,2H),4.71-4.43(m,1H),4.19(t,J=16.8,9.1Hz),3.57-3.34(m,2H),3.31-3.02(m,2H),2.90-2.60(m,1H),2.40-2.20(m,2H),2.10(dd,J=11.2,7.1Hz,1H),1.52-1.42(m,3H),1.15-1.09(m,6H),0.96(d,J=26.5Hz,6H),0.82(d,J=15.6Hz,3H).13C NMR(126MHz,DMSO-d6)δ169.7,145.5,138.3,127.9,126.6,125.6,118.1,111.9,106.7,96.7,86.5,81.3,79.4,74.4,68.3,57.4,45.9,39.9,36.2,29.9,29.6,25.3,20.3,19.1,16.3,15.5,13.2,11.8.化合物8:1H NMR(400MHz,DMSO-d6)δ11.0(s,2H),8.88(s,1H),7.16(d,J=8.5Hz,20H),6.19(d,J=7.3Hz,2H),5.89-5.60(m,1H),4.60(t,J=10.6Hz,1H),4.54-4.44(m,2H),3.86-3.60(m,3H),2.74(d,J=4.0Hz,2H),2.14-2.01(m,J=11.2,7.1Hz,1H),1.74-1.56(m,4H),1.52(s,2H),0.91(t,J=11.2Hz,12H),0.82(d,J=16.7Hz,6H).13C NMR(126MHz,DMSO-d6)δ173.7,156.2,139.7,138.3,135.5,127.9,124.8,121.4,111.9,106.4,86.5,83.4,79.8,78.3,75.9,74.1,70.6,68.3,67.9,57.4,45.6,34.2,30.9,25.3,20.3,18.7,16.3,15.9,12.1.
化合物9:1H NMR(400MHz,DMSO-d6)δ15.84(s,2H),7.65(s,20H),7.12(d,J=20.3Hz,11H),6.65(d,J=15.3Hz,1H),6.09(d,J=10.3Hz,1H),5.79-5.58(m,1H),4.71(s,1H),4.54-4.35(m,1H),4.11-3.96(m,3H),3.84-3.74(m,1H),3.57(dd,J=10.2,5.2Hz,2H),3.33-3.20(m,1H),2.70(dt,J=11.6,4.4Hz,8H),2.13(dd,J=11.2,7.1Hz,3H),1.99-1.80(m,11H),1.48(s,1H),1.20(d,J=6.4Hz,6H),0.74(dd,J=12.8,7.6Hz,9H).13C NMR(126MHz,DMSO-d6)δ189.8,173.7,139.7,124.8,127.9,111.9,103.3,93.6,86.7,79.4,72.3,68.3,62.5,57.4,45.9,39.9,36.8,36.2,30.3,27.5,20.3,18.6,16.3,15.9,13.2,11.9.
化合物10:1H NMR(400MHz,DMSO-d6)δ9.88(s,2H),7.88(s,22H),7.41(t,J=7.33Hz,10H),6.83-6.68(m,1H),6.32(d,J=7.5Hz,1H),5.75-5.51(m,3H),5.40-5.21(m,1H),4.82(t,J=10.6,2H),1H),4.10-3.86(m,3H),3.77-3.65(dd,J=10.2,5.2Hz,1H),3.22-3.07(m,1H),2.60(d,J=16.2,1H),1.74(s,9H),1.05-0.91(m,12H),0.81(t,J=12.8Hz,6H).13C NMR(126MHz,DMSO-d6)δ173.7,153.8,142.3,139.7,129.2,118.1,106.4,93.3,81.3,70.6,68.3,67.9,57.4,57.1,45.6,40.5,39.9,36.8,33.3,29.9,20.3,18.7,17.3,15.9,13.2,12.9.
化合物11:1H NMR(400MHz,DMSO-d6)δ9.61(s,1H),8.15(s,1H),7.73(dd,J=19.3,9.2Hz,2H),6.94-6.87(m,2H),6.12-6.08(m,2H),6.05(d,J=7.3Hz,1H),5.82-5.61(m,3H),4.58(t,J=26.4Hz,1H),4.53-4.33(m,1H),4.11(t,J=18.4Hz,2H),3.88-3.72(m,1H),2.54-2.34(m,1H),2.11-1.84(m,4H),1.68-1.51(m,4H),1.15-0.95(m,1H),0.80(d,J=17.4Hz,3H).13C NMR(126MHz,DMSO-d6)δ173.7,163.1,153.8,142.1,139.7,127.9,121.4,118.1,117.7,103.3,95.5,79.8,74.1,68.3,67.9,57.1,45.6,40.5,36.2,36.1,33.4,30.6,25.3,20.3,15.9,12.5.
化合物12:1H NMR(400MHz,DMSO-d6)δ10.5(s,2H),7.62(s,8H),7.41(d,J=16.2Hz,2H),6.97-6.62(m,2H),6.52(s,2H),5.83-5.64(m,3H),4.92-4.78(m,1H),4.33-4.02(m,1H),3.93-3.76(m,5H),3.44-3.22(m,1H),2.46-2.15(m,6H),2.06-1.74(m,5H),1.58-1.35(m,6H),0.91(d,J=16.8Hz,2H),0.77(t,J=15.4Hz,9H).13C NMR(126MHz,DMSO-d6)δ156.3,140.7,138.6,137.3,128.8,125.4,121.1,118.6,106.4,103.3,86.5,81.3,79.8,72.6,70.6,68.3,57.4,57.1,40.5,39.9,34.4,34.3,31.5,29.9,21.3,20.3,18.7,17.3,17.2,16.3,15.9,12.0.
化合物13:1H NMR(400MHz,DMSO-d6)δ9.65(s,2H),7.72-7.51(m,10H),6.97-6.62(m,2H),5.62-5.44(t,J=19.3Hz,2H),5.02(m,2H),4.97-4.62(m,2H),3.95(t,J=18.4Hz,2H),3.02(s,1H),2.61-2.42(m,6H),2.25(dd,J=12.4,6.1Hz,2H),1.19-0.9 8(m,3H),0.66(t,J=18.4Hz,3H).13C NMR(126MHz,DMSO-d6)δ173.7,153.8,139.7,128.8,121.4,106.4,79.8,78.3,68.3,57.1,45.6,40.5,39.9,35.2,34.5,23.1,23.1,20.3,18.7,16.3,15.9,14.5,13.2,10.8.
化合物14:1H NMR(400MHz,DMSO-d6)δ13.86(s,2H),9.82(d,J=5.6Hz,2H),7.63(s,1H),6.82-6.52(m,2H),5.98(d,J=7.3Hz,1H),5.50-5.34(t,J=22.4Hz,2H),4.89-4.50(m,1H),3.94-3.65(m,6H),2.84(d,J=22.1 1H),1.80-1.63(m,5H),1.22(d,J=9.4Hz,6H),0.92(s,1H),0.89(t,J=10.4Hz,6H).13C NMR(126MHz,DMSO-d6)δ188.5,154.4,139.7,127.9,118.1,102.9,95.9,92.9,81.3,79.4,74.4,72.3,68.3,60.8,60.8,57.4,45.9,40.5,34.6,30.2,25.3,20.3,19.1,16.3,15.9,13.2,11.9.
化合物15:1H NMR(400MHz,DMSO-d6)δ13.3(s,2H),7.82(s,6H),7.62(dt,J=19.3Hz,8.32Hz,12H),6.92(t,J=11.3Hz,2H),5.78-5.64(m,3H),5.51-5.30(t,J=19.3Hz,2H),4.83-4.63(m,1H),4.56(t,J=26.4Hz,2H),4.10(d,J=18.4Hz,2H),4.05–3.98(m,5H),3.85(dd,J=10.2,5.2Hz,2H),3.02(s,2H),2.46-2.25(m,1H),1.90-1.74(m,5H),1.23(d,J=6.4Hz,6H),1.05-0.96(m,3H),0.91(t,J=16.7Hz,9H).13C NMR(126MHz,DMSO-d6)δ188.5,173.7,150.7,141.2,136.0,129.7,121.4,118.1,113.9,106.7,103.3,86.5,85.5,81.3,79.4,71.3,68.3,62.5,57.6,57.2,39.9,31.5,29.9,29.6,17.6,17.3,16.3,15.9,13.2,11.1.
化合物16:1H NMR(400MHz,DMSO-d6)δ12.8(s,2H),8.12-8.02(m,2H),7.82(dd,J=19.3Hz,8.32Hz,1H),6.89(d,J=9.25,1H),6.12(s,1H),5.85-5.60(m,2H),5.52-5.20(m,1H),4.52(t,J=26.4Hz,2H),3.98(t,J=21.5Hz,2H),3.44-3.30(m,11H),2.78(d,J=16.3Hz,2H),1.19(s,6H),0.97(t,J=18.5,8.5Hz,3H),0.74(t,J=16.4Hz,6H).13C NMR(126MHz,DMSO-d6)δ173.7,166.7,146.4,135.5,135.4,128.6,121.4,119.9,106.7,96.7,79.4,78.8,68.3,57.6,53.6,45.9,40.5,39.9,35.2,31.3,25.3,20.3,19.1,16.3,15.9,13.2,12.0.
化合物17:1H NMR(400MHz,DMSO-d6)δ8.92(s,1H),7.76(s,9H),7.72(d,J=15.7Hz,19H),6.75(s,2H),5.92(d,J=12.0Hz,1H),5.77-5.66(m,3H),4.56-4.35(m,2H),4.01(t,J=18.4Hz,2H),3.38(t,J=25.7Hz,2H),3.02(t,J=5.5Hz,2H),2.60(d,J=16.7Hz,2H),1.93-1.75(m,5H),1.62-1.42(m,3H),0.92(d,J=26.8Hz,3H),0.81(t,J=15.5Hz,9H).13C NMR(126MHz,DMSO-d6)δ163.7,155.9,145.5,139.7,135.5,127.9,117.7,103.3,96.5,81.3,79.8,70.6,68.3,57.4,45.6,40.5,39.9,36.7,34.2,29.9,18.7,17.3,16.3,15.9,13.2,10.9.
化合物18:1H NMR(400MHz,DMSO-d6)δ11.39(s,3H),8.35(s,9H),7.84(d,J=11.6Hz,6H),6.54(s,1H),6.32(d,J=10.5Hz,1H),5.96(d,J=9.6Hz,1H),5.53-5.41(m,3H),4.90(t,J=13.3Hz,1H),3.72-3.54(m,1H),3.41(t,J=13.6Hz,2H),2.83(d,J=13.6Hz,1H),2.08-1.89(m,2H),1.15(t,J=18.4Hz,3H),0.99(t,J=39.2Hz,9H),0.88(t,J=23.5,10.2Hz,9H).13C NMR(126MHz,DMSO-d6)δ173.7,152.6,143.8,131.2,131.0,129.0,127.9,121.4,106.4,96.5,81.3,72.6,70.6,69.7,57.4,57.1,52.7,45.6,40.8,36.4,36.1,31.3,29.2,20.6,18.7,17.2,15.0,13.2,10.9.
化合物19:1H NMR(400MHz,DMSO-d6)δ9.26(s,3H),7.89(s,8H),7.20(d,J=12.5Hz,22H),6.31(s,9H),6.13(d,J=11.5Hz,1H),5.75-5.63(m,1H),4.84-4.71(m,1H),3.92-3.71(m,4H),3.65-3.54(m,3H),3.45(s,1H),2.54(dd,J=8.2,5.2Hz,1H),2.11-1.81(m,8H),1.31-1.19(m,18H),0.98(t,J=11.4Hz,3H),0.81(t,J=31.2Hz,6H).13C NMR(126MHz,DMSO-d6)δ173.7,149.6,139.1,135.1,129.7,106.4,103.3,79.8,72.3,70.6,57.5,45.6,40.8,39.8,36.1,31.6,29.2,25.7,25.1,24.1,23.5,23.1,20.3,18.6,13.3,13.0,12.6,11.4.
化合物20:1H NMR(400MHz,DMSO-d6)δ9.62(s,1H),7.69(s,3H),7.42(s,12H),6.81(s,1H),6.03(d,J=11.5Hz,1H),5.79-5.68(m,1H),4.81-4.67(t,J=11.6Hz,1H),3.99-3.82(m,1H),3.52(t,J=6.33Hz,2H),2.80(d,J=13.6Hz,1H),2.40-2.17(m,1H),2.06-1.83(m,23H),1.18-1.05(m,1H),0.98(t,J=13.5Hz,3H),0.84(t,J=36.2Hz,4H).13CNMR(126MHz,DMSO-d6)δ173.6,155.6,144.2,135.5,128.5,124.8,118.1,106.4,103.3,92.3,86.5,79.8,75.9,74.1,67.9,57.6,57.1,45.6,40.8,32.1,32.0,29.2,23.6,23.4,23.3,20.3,17.3,13.3,13.0,11.7.
化合物21:1H NMR(400MHz,DMSO-d6)δ9.85(s,8H),7.71(s,4H),6.89-6.51(m,2H),6.15(d,J=11.5Hz,1H),5.44-5.31(m,3H),4.82-4.75(m,1H),4.68-4.46(m,2H),4.12-3.79(m,3H),3.69-3.60(m,3H),2.78-2.51(m,1H),2.43-2.12(m,4H),1.75-1.66(m,14H),1.45-1.12(m,10H),1.05(t,J=18.4Hz,3H),0.86(t,J=33.4Hz,9H).13C NMR(126MHz,DMSO-d6)δ171.5,165.7,145.2,135.5,129.9,129.6,121.8,106.4,103.3,95.3,86.5,79.8,78.3,72.6,72.5,70.0,67.9,67.1,57.2,40.8,39.8,35.1,33.1,30.2,20.3,18.7,17.3,17.2,13.1,12.0,11.8.
化合物22:1H NMR(400MHz,DMSO-d6)δ11.86(s,3H),8.52(s,9H),7.79(s,4H),6.40(s,1H),6.21(d,J=10.5Hz,1H),5.98-5.62(m,1H),4.98-4.72(mz,1H),4.12-3.79(m,3H),3.70-3.52(m,2H),3.20-2.98(m,3H),2.77(d,J=11.4Hz,1H),2.08-1.64(m,17H),1.61-1.48(m,3H),1.14(d,J=28.6Hz,6H),0.96(t,J=17.7Hz,3H),0.81(t,J=32.3Hz,6H).13C NMR(126MHz,DMSO-d6)δ160.5,151.8,141.7,139.7,135.2,120.5,117.6,114.7,92.6,91.4,81.3,79.4,75.9,74.1,72.6,72.5,70.6,69.1,67.0,57.5,45.6,40.7,39.6,38.1,35.2,31.5,29.3,25.4,21.5,18.7,17.3,13.1,11.9,11.8.
化合物23:1H NMR(400MHz,DMSO-d6)δ12.78(s,3H),8.55(s,3H),7.92(d,J=9.4Hz,3H),6.50(s,1H),6.29(d,J=10.5Hz,1H),5.89-5.68(m,3H),5.42-5.36(m,2H),4.62(t,J=10.4Hz,2H),4.41-4.26(m,1H),3.99-3.60(m,7H),2.78(d,J=10.6Hz,2H),2.50(dd,J=5.9,4.2Hz,1H),2.10-1.85(m,5H),1.79-1.48(m,18H),1.17(d,J=26.7Hz,12H),0.96(t,J=19.7Hz,2H),0.81(t,J=33.4Hz,4H).13C NMR(126MHz,DMSO-d6)δ173.7,155.1,148.2,139.7,132.5,129.9,121.1,119.9,115.2,107.8,103.3,97.6,93.2,86.8,81.4,79.4,78.9,71.8,67.3,57.4,45.9,41.1,39.6,36.2,34.1,33.5,30.6,22.2,20.2,19.7,17.2,16.1,14.0,13.9.
化合物24:1H NMR(400MHz,DMSO-d6)δ12.61(s,3H),9.21(s,3H),7.49(d,J=13.5Hz,6H),7.24(d,J=19.9Hz,6H),6.52(s,1H),6.45(d,J=9.5Hz,1H),5.68-5.52(m,6H),4.89-4.79(m,1H),4.33-4.25(m,1H),4.16-3.77(m,5H),3.47-3.37(m,1H),2.94-2.81(m,1H),2.65(dd,J=5.9,4.2Hz,1H),1.64-1.45(m,5H),1.17(d,J=29.9Hz,18H),0.97(t,J=19.7Hz,3H),0.84(t,J=35.3Hz,6H).13C NMR(126MHz,DMSO-d6)δ171.5,159.6,144.2,144.1,139.7,134.2,129.3,120.3,106.4,103.1,86.5,79.8,78.5,72.6,69.4,67.0,57.4,54.1,40.8,39.9,38.0,35.1,34.6,29.2,27.1,22.3,20.1,18.7,17.3,16.2,14.7,11.8.
化合物25:1H NMR(400MHz,DMSO-d6)δ11.98(s,3H),8.21(s,16H),7.62(s,9H),7.35(d,J=23.6Hz,6H),6.31(d,J=8.4Hz,1H),5.23(d,J=5.5Hz,1H),4.80-4.77(m,1H),4.60(t,J=19.9Hz,2H),4.16-3.98(m,2H),3.45-3.23(m,2H),2.94-2.63(m,4H),2.31-2.18(m,2H),2.04-1.71(m,11H),1.27(d,J=3.2Hz,18H),0.99(t,J=32.4Hz,6H),0.82(d,J=25.6Hz,6H).13C NMR(126MHz,DMSO-d6)δ173.1,159.2,144.2,139.7,138.1,129.5,127.5,121.4,119.1,106.3,92.9,86.7,79.8,70.1,67.5,58.4,57.4,45.1,36.3,35.1,34.3,29.5,20.3,19.2,18.8,17.3,15.4,13.1,12.8.
化合物26:1H NMR(400MHz,DMSO-d6)δ8.97(d,J=34.7Hz,0H),8.23(s,1H),7.80(d,J=8.1Hz,1H),7.18(d,J=7.5Hz,1H),7.13(t,J=7.8Hz,1H),6.94(t,J=7.4Hz,1H),3.34(s,2H),2.50(p,J=1.8Hz,1H),2.26(s,3H),1.64–0.59(m,0H),1.01–0.47(m,0H);13CNMR(126MHz,DMSO-d6)δ152.9,137.4,130.7,144.6,127.2,126.8,122.6,95.6,80.6,76.5,64.8,52.2,44.4,40.0,39.4,39.7,39.0,39.4,39.1,39.0,25.6,18.3,11.8.
化合物27:1H NMR(400MHz,DMSO-d6)δ10.01(s,1H),8.84(s,24H),7.44(d,J=2.1Hz,82H),5.89–5.80(m,1H),5.13(s,1H),4.91–4.87(m,0H),4.49(d,J=14.5Hz,1H),3.89(d,J=5.4Hz,1H),3.29(s,1H),3.27(s,1H),3.14(s,1H),2.52–2.47(m,12H),2.20(q,J=7.8Hz,3H),1.52(dd,J=13.1,8.1Hz,1H),1.47(s,2H),1.39(d,J=8.1Hz,1H),1.15(d,J=16.9Hz,1H),1.12(s,1H),1.09(d,J=15.1Hz,0H),1.09(s,2H),0.93–0.76(m,8H);13CNMR(126MHz,DMSO-d6)δ138.93,131.51,131.49,120.21,119.5,113.36,95.8,88.6,80.2,76.5,71.2,66.4,59.9,55.5,40.00,39.83,39.67,39.50,39.33,36.17,30.00,26.4,20.6,18.,15.,12.6.
化合物28:1H NMR(400MHz,DMSO-d6)δ9.76(s,3H),8.25(s,9H),7.51(s,2H),6.40(s,1H),5.68(dd,J=15.6,9.8Hz,1H),5.60(d,J=4.7Hz,1H),4.71(d,J=8.0Hz,1H),4.59(d,J=14.4Hz,1H),3.79(dd,J=15.9,8.0Hz,1H),3.62-3.53(m,1H),2.11(s,1H),2.07(s,0H),1.73(s,2H),1.14(d,J=28.6Hz,6H),0.96(t,J=17.7Hz,3H),0.81(t,J=32.3Hz,6H).13C NMR(126MHz,DMSO-d6)δ150.6,141.6,139.7,130.2,111.6,85.6,85.1,84.6,79.4,77.9,76.1,73.4,72.5,70.6,66.2,66.1,46.5,46.4,40.7,38.6,38.1,33.1,33.0,28.3,24.4,21.5,19.7,19.3,13.1,12.9,11.8.
化合物29:1H NMR(400MHz,DMSO-d6)δ11.65(s,3H),9.23(s,3H),7.7.6(d,J=11.2Hz,3H),6.29(d,J=10.5Hz,1H),5.79-5.58(m,3H),4.95(t,J=12.4Hz,2H),3.89-3.55(m,8H),2.50(dd,J=5.9,4.2Hz,1H),2.22-1.89(m,1H),1.59-1.35(m,11H),0.96(t,J=23.1Hz,2H),0.81(t,J=36.1Hz,4H).13C NMR(126MHz,DMSO-d6)δ173.7,156.2,139.7,1338.5,121.9,121.1,119.9,107.8,97.6,97.2,86.8,81.4,79.4,78.9,76.2,74.2,71.8,67.3,57.4,45.9,43.2,38.6 36.2,33.2,33.0,30.6,19.7,17.2,17.0,14.0,12.9.
化合物30:1H NMR(400MHz,DMSO-d6)10.00(s,1H),9.45(s,24H),7.38-7.29(m,20H),6.52-6.20(m,3H),5.37(d,J=4.5Hz,1H),5.23(d,J=3.8Hz,1H),4.42(s,2H),3.89(d,J=5.1Hz,1H),3.39-3.30(m,2H),3.27-3.12(m,1H),2.50(p,J=1.9Hz,11H),2.08(d,J=8.8Hz,1H),1.73(s,2H),1.60(s,1H),1.47(s,2H),1.41-1.25(m,1H),1.21(s,4H),1.16-1.09(m,6H),0.96(dd,J=16.3,6.5Hz,2H),0.88(dt,J=20.7,7.1Hz,5H).13C NMR(126MHz,DMSO-d6)δ152.5,140.5,139.0,138.7,134.7,119.3,117.3,113.79,98.6,85.6,81.3,79.2,78.8,75.4,72.6,70.6,69.5,68.7,67.2,57.1,44.2,42.6,41.6,39.1,36.5,34.3,33.9,32.4,31.8,27.2,25.6,21.0,20.9,19.7,18.7,17.1,14.0,13.1,12.0
化合物31:1H NMR(400MHz,DMSO-d6)δ8.84(d,J=37.6Hz,3H),8.20(s,1H),7.56(d,J=10.6Hz,10H),6.94(t,J=7.4Hz,9H),6.62-6.30(m,7H),5.60(d,J=4.7Hz,1H),5.56-5.40(m,3H),4.71(d,J=8.0Hz,1H),4.59(d,J=25.7Hz,1H),3.89(d,J=5.4Hz,1H),3.75-3.63(m,1H),3.51-3.40(m,1H),3.34(s,2H),2.50(d,J=1.8Hz,1H),2.26(s,3H),2.11-1.87(m,2H),1.18(d,J=9.2Hz,2H),1.11-0.97(m,2H).13C NMR(126MHz,DMSO-d6)δ156.7,139.5,138.6,135.2,130.17,129.7,124.8,122.66,119.8,98.2,77.5,77.4,76.4,70.5,68.9,68.2,65.2,56.8,45.9,40.0,36.8,36.7,35.6,35.5,31.3,30.7,18.3,17.1,13.6,11.7.
化合物32:1H NMR(400MHz,DMSO-d6)δ9.54(s,20H),7.86-7.65(m,23H),6.54-6.41(m,2H),5.89-5.80(m,1H),5.13(s,1H),4.51(d,J=16.5Hz,1H),4.09(d,J=13.5Hz,1H),3.92-3.71(m,1H),3.41(d,J=10.1Hz,1H),3.33-3.28(m,1H),2.74-2.50(m,12H),2.23(d,J=9.6Hz,3H),1.78(dd,J=14.2,9.6Hz,1H),1.49-1.52(m,1H),1.15-1.09(m,6H),0.81(d,J=20.7Hz,5H).13C NMR(126MHz,DMSO-d6)δ158.2,135.9,135.1,134.6,131.51,129.4,119.5,118.5,101.5,95.6,83.6,79.5,77.6,77.1,74.2,70.9,67.5,67.1,69.5,58.2,57.6,45.6,44.2,43.6,38.6,38.5,34.5,30.5,29.2,29.1,27.5,26.4,21.5,20.6,19.8,18.4,17.5,16.5,12.5.
1.2利用HPLC分析表1中多种化合物
色谱柱:C18反相柱,150mm×4.6mm
流动相:乙腈:水=80:2 0
吸收波长:250nm
流速:1mL/min
柱温:25℃.
结果如表2所示。
表2表1中多种化合物HPLC分析结果
化合物 | 保留时间 | 化合物 | 保留时间 | 化合物 | 保留时间 |
化合物10 | 4.06 | 化合物11 | 5.52 | 化合物12 | 4.20 |
化合物13 | 5.01 | 化合物14 | 4.80 | 化合物15 | 5.26 |
化合物16 | 5.15 | 化合物17 | 4.35 | 化合物18 | 4.55 |
化合物19 | 4.40 | 化合物20 | 4.76 | 化合物21 | 3.95 |
化合物22 | 4.30 | 化合物23 | 5.01 | 化合物24 | 4.60 |
化合物25 | 6.65 | 化合物26 | 4.55 | 化合物27 | 6.78 |
化合物28 | 3.56 | 化合物29 | 6.59 | 化合物30 | 4.05 |
化合物31 | 4.65 | 化合物32 | 4.75 | 化合物33 | 4.10 |
1.3研究发现本发明公开的新化合物相比于其母体结构,对光的稳定性显著增强
具体结果如表3所示。
表3表1中多个新化合物的光稳定性研究结果
由表3可知,相比于母体结构,新化合物的抗光解能力明显增强,这一特性能延长药物在叶面的持效期,减少施药次数,非常有利于对虫害的防治。
二、农药制剂实施例
实施例34
以质量百分含量计,本实施例可湿性粉剂由下述组分组成:
实施例35
以质量百分含量计,本实施例悬浮剂由下述组分组成:
实施例36
以质量百分含量计,本实施例水分散粒剂由下述组分组成:
实施例37
以质量百分含量计,本实施例乳油由下述组分组成:
三、生物活性实施例
将表1中所示化合物1-33分别进行生物活性试验。将化合物用N,N-二甲基甲酰胺溶解后,用0.1%T-80水溶液稀释成5个梯度浓度,以每个浓度的对数值为横坐标,对应死亡率的机率值为纵坐标建立毒力回归方程,计算EC50值,结果见表4、表5、表6和表7。
表4
表5
表6
表7
四、田间试验实施例
4.1对二斑叶螨的防治
按照实施例35、2)的方法将化合物1、化合物2、化合物14、化合物21、化合物23、化合物30制成制剂,和母体结构阿维菌素B1a进行田间试验,比较其对二斑叶螨的防治效果。结果如表8所示。
表8对二斑叶螨的防治效果
由表8的结果可以看出,在新化合物对二斑叶螨的田间试验中,新化合物在持效性上明显优于母体结构,这与新化合物的抗光解能力增强有关。
4.2对柑桔全爪螨的防治
以质量百分含量计,可湿性粉剂由下述组分组成:
选择5%化合物2+10%哒螨灵可湿性粉剂,2%化合物12+8%哒螨灵可湿性粉剂、2%化合物21+8%哒螨灵可湿性粉剂分别进行防治柑桔全爪螨的田间试验,分别于施药后1、3、7天调查防效,结果如表9所示。
表9对柑桔全爪螨的防治效果
由表9可知,在新化合物对柑桔全爪螨的田间试验中,新化合物与哒螨灵复配使用后对害虫的防治效果明显高于阿维菌素和哒螨灵单独使用,说明新化合物与哒螨灵混合使用对螨类害虫存在一定的增效作用。
4.3对斑潜蝇的防治
以质量百分含量计,本实施例悬浮剂由下述组分组成:
选择2%化合物4+4%高效氯氰菊酯悬浮剂,3%化合物21+9%高效氯氰菊酯悬浮剂、2%化合物33+4%高效氯氰菊酯悬浮剂分别进行防治斑潜蝇的田间试验,分别与施药后3、7、15天调查防效,结果如表10所示。
表10对斑潜蝇的防治效果
由表10可知,在新化合物对斑潜蝇的田间试验中,新化合物与高效氯氰菊酯复配使用后对害虫的防治效果明显高于阿维菌素和高效氯氰菊酯单独使用,说明新化合物与高效氯氰菊酯混合使用对潜蝇科害虫存在一定的增效作用。
4.4对根结线虫的防治
以质量百分含量计,本实施例悬浮剂由下述组分组成:
选择1%化合物16+3%氟吡菌酰胺悬浮剂,1%化合物21+3%氟吡菌酰胺悬浮剂、2%化合物30+10%氟吡菌酰胺悬浮剂分别进行防治根结线虫的田间试验,分别于施药后60、90天调查防效,结果如表11所示。
表11对根结线虫的防治效果
由表11可知在新化合物对根结线虫的田间试验中,新化合物与氟吡菌酰胺复配使用后对害虫的防治效果明显高于阿维菌素和氟吡菌酰胺单独使用,说明新化合物与氟吡菌酰胺混合使用对线虫存在一定的增效作用。
4.5对棉铃虫的防治
以质量百分含量计,本实施例悬浮剂由下述组分组成:
选择3%化合物15悬浮剂,3%化合物30悬浮剂、3%化合物32悬浮剂分别进行防治棉花棉铃虫的田间试验,分别于施药后3、9天调查防效,结果如表12所示。
表12对棉铃虫的防治效果
由表12可知在新化合物对棉铃虫的田间试验中,药后3天时新化合物对害虫的防治效果与阿维菌素的防效差别不大,药后9天时,新化合物对害虫的防效在61-77%范围内,而1.8%阿维菌素乳油的防效仅为42%,说明新化合物对棉铃虫的防效明显优于阿维菌素。
4.6对棉花烟粉虱的防治
以质量百分含量计,本实施例悬浮剂由下述组分组成:
选择3%化合物17悬浮剂,3%化合物20悬浮剂、3%化合物23悬浮剂、3%化合物24悬浮剂分别进行防治棉花烟粉虱的田间试验,分别于施药后3、5天调查防效,结果如表13所示。
表13对烟粉虱的防治效果
由表13可知在新化合物对烟粉虱的田间试验中,药后3天时新化合物对害虫的防治效果比阿维菌素的防效高出4-7个百分点,药后5天时,新化合物对害虫的防效比1.8%阿维菌素乳油的防效高出7-18个百分点,说明新化合物对烟粉虱的防效明显优于阿维菌素。
4.6本发明大环内酯类衍生物对真菌的抑制作用研究
采用菌丝生长速率法测定了化合物对禾谷镰刀菌(Fusariumgraminearum Schw.)的室内活性,结果如表14所示。
表14本发明大环内酯类衍生物对禾谷镰刀菌的抑制作用结果
采用菌丝生长速率法测定了化合物对立枯丝核菌(Rhixoctonia solani.)的室内活性,结果如表15所示。
表15本发明大环内酯类衍生物对立枯丝核菌的抑制作用结果
采用菌丝生长速率法测定了化合物对番茄灰霉病菌(Botrytis cinerea Pers.)的室内活性,结果如表16所示。
表16本发明大环内酯类衍生物对番茄灰霉病菌的抑制作用结果
由表14、15、16可知,本发明新发现的化合物,对真菌的生长具有一定的抑制作用。在农业生长中,作物上的病虫害往往是同时发生,所以,兼有抑制病原菌和害虫生长的特性,对于有害生物防治,降低农药用量具有非常重要的现实意义。本发明发现的化合物具有巨大的应用价值和开发潜力,具有广阔的市场前景。
Claims (6)
3.如权利要求2所述大环内酯类衍生物的合成方法,其特征在于:所述化合物A与化合物B的摩尔比为1:0.5~1:10;催化剂为氯化亚锡、四丁基锡、醋酸三丁基锡、三氯正丁基锡、三甲基锡氢氧化物、二氯二甲基锡、二月桂酸二丁基锡中的任意一种。
4.如权利要求1所述大环内酯类衍生物在防治害虫中的用途;所述害虫包括蛛形纲、双壳纲、腹足纲、线虫纲、唇足目、弹尾目、虱目、双翅目、鞘翅目、直翅目、异翅亚目、同翅目、膜翅目、等翅目、鳞翅目、食毛目、啮虫目、蚤目、缨翅目、缨尾目。
5.如权利要求1所述大环内酯类衍生物在制备抑制真菌生长的药物中的用途。
6.如权利要求1所述大环内酯类衍生物与成分C的混合物在防治害虫中的用途;所述害虫包括蛛形纲、双壳纲、腹足纲、线虫纲、唇足目、弹尾目、虱目、双翅目、鞘翅目、直翅目、异翅亚目、同翅目、膜翅目、等翅目、鳞翅目、食毛目、啮虫目、蚤目、缨翅目、缨尾目;所述成分C选自哒螨灵、稻瘟灵、氰氟虫腙、杀螨素、溴螨酯、噻螨酮、***锡、三环锡、苯丁锡、炔螨特、苯氟磺胺、唑螨酯、嘧螨胺、阿维菌素、甲氨基阿维菌素苯甲酸盐、伊维菌素、雷皮菌素、弥拜菌素、多杀菌素、乙基多杀菌素、苏云金素、印楝素、鱼藤酮、藜芦碱、杀虫单、杀虫双、氯虫酰胺、氯虫苯甲酰胺、溴氰虫酰胺、虫脲、噻嗪酮、氟啶脲、氟啶胺、灭蝇胺、环虫腈、除虫脲、氟螨脲、氟虫脲、氟铃脲、虱螨脲、氟酰脲、氟幼脲、氟苯脲、杀铃脲、灭幼脲、苯氧威、烯虫乙酯、烯虫酯炔、烯虫酯、吡丙醚、啶虫丙醚、环虫酰肼、氯虫酰肼、甲氧虫酰肼、虫酰肼、呋喃虫酰肼、氟啶虫酰胺、噻虫胺、噻虫嗪、噻虫啉、吡虫啉、啶虫脒、烯啶虫胺、呋虫胺、吡蚜酮、氟啶虫胺腈、哌虫胺、茚虫威、丁烯氟虫腈、唑虫酰胺、溴虫腈、螺螨酯、螺虫乙酯、丁醚脲、联苯菊酯、氟氯氰菊酯、高效氯氟氰菊酯、高效氟氯氰菊酯、高效氯氰菊酯、二嗪磷、辛硫磷、甲基嘧啶磷、噻唑膦中的一种或几种。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811413890.3A CN109516996B (zh) | 2018-11-26 | 2018-11-26 | 一种大环内酯类衍生物、其合成及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811413890.3A CN109516996B (zh) | 2018-11-26 | 2018-11-26 | 一种大环内酯类衍生物、其合成及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109516996A CN109516996A (zh) | 2019-03-26 |
CN109516996B true CN109516996B (zh) | 2021-12-17 |
Family
ID=65779107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811413890.3A Active CN109516996B (zh) | 2018-11-26 | 2018-11-26 | 一种大环内酯类衍生物、其合成及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109516996B (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN87108339A (zh) * | 1986-12-11 | 1988-07-13 | 三共株式会社 | 大环内酯化合物的制备和它们的用途 |
CN104231022A (zh) * | 2013-06-14 | 2014-12-24 | 南开大学 | 一种大环内酯类化合物的制备及应用 |
RU2627277C1 (ru) * | 2016-12-12 | 2017-08-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московская государственная академия ветеринарной медицины и биотехнологии - МВА имени К.И. Скрябина (ФГБОУ ВО МГАВМиБ - МВА имени К.И. Скрябина) | 4"-О,5-О-ди(метилкарбамат)ивермектина, способ его получения и антипаразитарное средство на его основе |
-
2018
- 2018-11-26 CN CN201811413890.3A patent/CN109516996B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN87108339A (zh) * | 1986-12-11 | 1988-07-13 | 三共株式会社 | 大环内酯化合物的制备和它们的用途 |
CN104231022A (zh) * | 2013-06-14 | 2014-12-24 | 南开大学 | 一种大环内酯类化合物的制备及应用 |
RU2627277C1 (ru) * | 2016-12-12 | 2017-08-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московская государственная академия ветеринарной медицины и биотехнологии - МВА имени К.И. Скрябина (ФГБОУ ВО МГАВМиБ - МВА имени К.И. Скрябина) | 4"-О,5-О-ди(метилкарбамат)ивермектина, способ его получения и антипаразитарное средство на его основе |
Non-Patent Citations (4)
Title |
---|
Phenyl Isocyanate-Modified Avermectin B1a Improves the Efficacy against Plant-Parasitic Nematode Diseases by Facilitating Its Soil Mobility;Tong-fang Jing et al.;《ACS Sustainable Chem. Eng.》;20200108;第8卷;第2310-2319页 * |
Synthesis of ivermectin-4"",5-diyl[bis(N-methylcarbamate)];A. N. Blinnikov et al.;《Russ.Chem.Bull.,Int.Ed.》;20180531;第67卷(第5期);第834页Scheme 1化合物3,第834页Scheme 1, * |
螺甲螨酯和弥拜霉素类似物的合成及其生物活性研究;季明华;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20110615(第6期);第48-49页第3.2.4部分,第43-47页 * |
阿维菌素衍生物设计、合成及杀虫活性研究;陈振;《中国优秀硕士学位论文全文数据库 农业科技辑》;20170515(第5期);D046-136 * |
Also Published As
Publication number | Publication date |
---|---|
CN109516996A (zh) | 2019-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN111132549B (zh) | 动物用体外寄生虫长效防除剂 | |
JP5313869B2 (ja) | 有害生物防除用組成物 | |
JP4015182B2 (ja) | 害虫防除剤 | |
JP5269609B2 (ja) | 害虫防除剤 | |
CN112930339B (zh) | (杂)芳基咪唑化合物及有害生物防除剂 | |
CN103254125A (zh) | 有害生物防除剂 | |
AU2018201101A1 (en) | Novel cyclic depsipeptide derivative and pest control agent comprising same | |
CN107406458B (zh) | 抗寄生虫化合物 | |
EP3344610B1 (en) | Spinosyn derivatives as insecticides | |
CN110734411A (zh) | 一种含有酰胺类化合物的药物组合物及其应用 | |
CN104542601A (zh) | 一种含有喹啉铜和春雷霉素的农药组合物及其应用 | |
CN107266511B (zh) | 一类新颖的5-肟酯B2a结构的化合物及其制备方法与应用 | |
CN102070607A (zh) | 具有杀虫活性的吡啶氮氧化物类新烟碱化合物及其用途 | |
CN109516996B (zh) | 一种大环内酯类衍生物、其合成及应用 | |
CN104203911A (zh) | 芳氧基脲化合物和有害生物防除剂 | |
CN104231022B (zh) | 一种大环内酯类化合物的制备及应用 | |
CN103025161A (zh) | 有害生物防治剂 | |
CN103613625B (zh) | 一种阿维菌素类化合物及其制备方法和在农药中的用途 | |
CN107337682B (zh) | 13-酰基化阿维菌素B2a苷元衍生物及其制备方法和用途 | |
JP5037164B2 (ja) | 害虫防除剤 | |
CN105153260B (zh) | 一种c21孕甾烷类衍生物及其制备方法和应用 | |
WO1996019920A1 (en) | Compositions for treating nematode infections in trees | |
CN107501368A (zh) | 一种新型多拉菌素衍生物的合成及其杀虫应用 | |
CN104119268A (zh) | 具有杀虫活性的含三氟乙酰基新烟碱化合物的制备与用途 | |
JP2023015111A (ja) | アジリジンスピノシン誘導体および製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |