TW202112237A - Nematicidal compositions - Google Patents
Nematicidal compositions Download PDFInfo
- Publication number
- TW202112237A TW202112237A TW109126846A TW109126846A TW202112237A TW 202112237 A TW202112237 A TW 202112237A TW 109126846 A TW109126846 A TW 109126846A TW 109126846 A TW109126846 A TW 109126846A TW 202112237 A TW202112237 A TW 202112237A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- alkoxy
- alkyl
- haloalkyl
- compound
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 121
- 230000001069 nematicidal effect Effects 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 241000244206 Nematoda Species 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 34
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 160
- 241000196324 Embryophyta Species 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- 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 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 20
- 229960001591 cyfluthrin Drugs 0.000 claims description 19
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 18
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 16
- 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 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000005660 Abamectin Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 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 13
- 239000005944 Chlorpyrifos Substances 0.000 claims description 12
- 239000005893 Diflubenzuron Substances 0.000 claims description 12
- 229950008167 abamectin Drugs 0.000 claims description 12
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 12
- 229940019503 diflubenzuron Drugs 0.000 claims description 12
- 239000002917 insecticide Substances 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 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 11
- 239000005875 Acetamiprid Substances 0.000 claims description 11
- 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 10
- 239000005946 Cypermethrin Substances 0.000 claims description 10
- 239000005899 Fipronil Substances 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 240000004460 Tanacetum coccineum Species 0.000 claims description 10
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 10
- 229960005424 cypermethrin Drugs 0.000 claims description 10
- 229940013764 fipronil Drugs 0.000 claims description 10
- 229940015367 pyrethrum Drugs 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 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 9
- 230000000967 entomopathogenic effect Effects 0.000 claims description 9
- 229960000490 permethrin Drugs 0.000 claims description 9
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 9
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 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 8
- PHCCDUCBMCYSNQ-UHFFFAOYSA-N fluazaindolizine Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC(=O)C=2N=C3C(Cl)=CC(=CN3C=2)C(F)(F)F)=C1 PHCCDUCBMCYSNQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- DZVWKNFPXMUIFA-UHFFFAOYSA-N pyflubumide Chemical compound C1=C(CC(C)C)C(C(OC)(C(F)(F)F)C(F)(F)F)=CC=C1N(C(=O)C(C)C)C(=O)C1=C(C)N(C)N=C1C DZVWKNFPXMUIFA-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 239000005888 Clothianidin Substances 0.000 claims description 7
- 239000005897 Etoxazole Substances 0.000 claims description 7
- 239000005925 Pymetrozine Substances 0.000 claims description 7
- 239000005931 Spirotetramat Substances 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 7
- 239000002158 endotoxin Substances 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 7
- 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 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
- 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 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
- 239000005878 Azadirachtin Substances 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 6
- 239000005874 Bifenthrin Substances 0.000 claims description 6
- 239000005886 Chlorantraniliprole Substances 0.000 claims description 6
- 239000005892 Deltamethrin Substances 0.000 claims description 6
- 239000005894 Emamectin Substances 0.000 claims description 6
- 239000005783 Fluopyram Substances 0.000 claims description 6
- 239000005906 Imidacloprid Substances 0.000 claims description 6
- 239000005907 Indoxacarb Substances 0.000 claims description 6
- 239000005912 Lufenuron Substances 0.000 claims description 6
- 239000005929 Spinetoram Substances 0.000 claims description 6
- 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
- 239000005940 Thiacloprid Substances 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
- 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 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
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-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
- 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
- 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 claims description 6
- BKACAEJQMLLGAV-PLNGDYQASA-N heptafluthrin Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)C1C(C)(C)C1\C=C/C(F)(F)F BKACAEJQMLLGAV-PLNGDYQASA-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
- 229960000521 lufenuron Drugs 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
- 229930002897 methoprene Natural products 0.000 claims description 6
- 229950003442 methoprene Drugs 0.000 claims description 6
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 claims description 5
- 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 5
- 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 claims description 5
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 5
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 5
- 239000005945 Chlorpyrifos-methyl Substances 0.000 claims description 5
- 239000005891 Cyromazine Substances 0.000 claims description 5
- 239000005947 Dimethoate Substances 0.000 claims description 5
- 239000005898 Fenoxycarb Substances 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(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-RUTXASTPSA-N 0.000 claims description 5
- KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 claims description 5
- FMPFURNXXAKYNE-UHFFFAOYSA-N [2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]quinolin-4-yl] methyl carbonate Chemical compound C1=C2C(OC(=O)OC)=C(C)C(CC)=NC2=CC(C)=C1OC1=CC=C(OC(F)(F)F)C=C1 FMPFURNXXAKYNE-UHFFFAOYSA-N 0.000 claims description 5
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 5
- 229950000775 cyromazine Drugs 0.000 claims description 5
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 229940079888 nitenpyram Drugs 0.000 claims description 5
- 229930185156 spinosyn Natural products 0.000 claims description 5
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000005828 Pyrimethanil Substances 0.000 claims description 4
- 239000005664 Spirodiclofen Substances 0.000 claims description 4
- 239000005665 Spiromesifen Substances 0.000 claims description 4
- KVIZNNVXXNFLMU-AIIUZBJTSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1r,3r)-2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C\C KVIZNNVXXNFLMU-AIIUZBJTSA-N 0.000 claims description 4
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical class N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 claims description 4
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- GNXDAGCMYJCRIB-UFYBRSFPSA-N propan-2-yl (2e,4e)-11-methoxy-3,7,11-trimethyl-dodeca-2,4-dienoate Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C\C(=O)OC(C)C.COC(C)(C)CCCC(C)C\C=C\C(\C)=C\C(=O)OC(C)C GNXDAGCMYJCRIB-UFYBRSFPSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000002755 pyrazolinyl 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
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- 150000003227 pyridoxines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 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 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical class C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229940125794 sodium channel blocker Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229960005559 sulforaphane Drugs 0.000 description 1
- 235000015487 sulforaphane Nutrition 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
控制植物寄生線蟲在實現高作物效率中是極其重要的。線蟲引起的根損害可引起作物產量和品質之顯著降低,並且從而導致消費者成本增加。由於線蟲寄生蟲對驅蟲劑的抗性的廣泛發展,儘管有可用的化學治療劑,但線蟲繼續在家畜中引起問題。對更有效、成本更低、毒性更低、對環境更安全或具有不同的作用模式的新型化合物存在持續需求。定義 Controlling plant parasitic nematodes is extremely important in achieving high crop efficiency. Root damage caused by nematodes can cause a significant reduction in crop yield and quality, and thereby increase consumer costs. Due to the widespread development of resistance of nematode parasites to repellents, nematodes continue to cause problems in livestock despite the availability of chemotherapeutics. There is a continuing need for new compounds that are more effective, lower cost, less toxic, safer for the environment, or have different modes of action. definition
在定義中給出的實例通常是非詳盡的,並且不得被解釋為限制本文件中所揭露之分子。可以理解的是,取代基應相對於與其附接的特定分子遵從化學鍵合規則和空間相容性約束。The examples given in the definition are generally non-exhaustive and should not be construed as limiting the elements disclosed in this document. It can be understood that the substituents should comply with chemical bonding rules and steric compatibility constraints with respect to the specific molecules to which they are attached.
「烯基 」意指由碳和氫組成的無環、不飽和(至少一個碳-碳雙鍵)、支鏈或直鏈的取代基,例如乙烯基、烯丙基、丁烯基、戊烯基、和己烯基。" Alkenyl " means an acyclic, unsaturated (at least one carbon-carbon double bond), branched or straight chain substituent composed of carbon and hydrogen, such as vinyl, allyl, butenyl, pentene Group, and hexenyl group.
「烯基氧基 」意指進一步由碳-氧單鍵組成的烯基,例如烯丙氧基、丁烯氧基、戊烯氧基、己烯氧基。"Alkenyloxy" means an alkenyl group further composed of a carbon-oxygen single bond, such as allyloxy, butenyloxy, pentenyloxy, and hexenyloxy.
「烷氧基 」意指進一步由碳-氧單鍵組成的烷基,例如甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、和三級丁氧基。"Alkoxy" means an alkyl group further composed of carbon-oxygen single bonds, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tertiary butoxy Oxy.
「烷基 」意指由碳和氫組成的無環、飽和、支鏈或直鏈的取代基,例如甲基、乙基、丙基、異丙基、丁基、和三級丁基。" Alkyl " means an acyclic, saturated, branched or linear substituent composed of carbon and hydrogen, such as methyl, ethyl, propyl, isopropyl, butyl, and tertiary butyl.
「炔基 」意指由碳和氫組成的無環、不飽和(至少一個碳-碳三鍵)、支鏈或直鏈的取代基,例如乙炔基、炔丙基、丁炔基、和戊炔基。" Alkynyl " means an acyclic, unsaturated (at least one carbon-carbon triple bond), branched or straight chain substituent composed of carbon and hydrogen, such as ethynyl, propargyl, butynyl, and pentyl Alkynyl.
「炔基氧基 」意指進一步由碳-氧單鍵組成的炔基,例如戊炔基氧基、己炔基氧基、庚炔基氧基、和辛炔基氧基。"Alkynyloxy" means an alkynyl group further composed of a carbon-oxygen single bond, such as pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy.
「芳基 」意指由氫和碳組成的環狀芳香族取代基,例如苯基、萘基、和聯苯基。" Aryl " means a cyclic aromatic substituent composed of hydrogen and carbon, such as phenyl, naphthyl, and biphenyl.
「環烯基 」意指由碳和氫組成的單環或多環不飽和(至少一個碳-碳雙鍵)取代基,例如環丁烯基、環戊烯基、環己烯基、降莰烯基、二環[2.2.2]辛烯基、四氫萘基、六氫萘基、和八氫萘基。" Cycloalkenyl " means a monocyclic or polycyclic unsaturated (at least one carbon-carbon double bond) substituent composed of carbon and hydrogen, such as cyclobutenyl, cyclopentenyl, cyclohexenyl, norbornanyl Alkenyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl, hexahydronaphthyl, and octahydronaphthyl.
「環烯基氧基 」意指進一步由碳-氧單鍵組成的環烯基,例如環丁烯基氧基、環戊烯基氧基、降莰烯基氧基、和二環[2.2.2]辛烯基氧基。"Cycloalkenyloxy" means a cycloalkenyl group further composed of a carbon-oxygen single bond, such as cyclobutenyloxy, cyclopentenyloxy, norbornyloxy, and bicyclo[2.2. 2] Octenyloxy.
「環烷基 」意指由碳和氫組成的單環或多環飽和取代基,例如環丙基、環丁基、環戊基、降莰基、二環[2.2.2]辛基、和十氫萘基。" Cycloalkyl " means a monocyclic or polycyclic saturated substituent composed of carbon and hydrogen, such as cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and Decahydronaphthyl.
「環烷氧基 」意指進一步由碳-氧單鍵組成的環烷基,例如環丙基氧基、環丁基氧基、環戊基氧基、降莰基氧基、和二環[2.2.2]辛基氧基。"Cycloalkoxy" means a cycloalkyl group further composed of a carbon-oxygen single bond, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[ 2.2.2] Octyloxy.
「鹵代 」意指氟、氯、溴、和碘。" Halo " means fluorine, chlorine, bromine, and iodine.
「鹵代烷氧基 」意指進一步由從一至最大可能數目的相同或不同的鹵基組成的烷氧基,例如氟甲氧基、三氟甲氧基、2,2-二氟丙氧基、氯甲氧基、三氯甲氧基、1,1,2,2-四氟乙氧基、和五氟乙氧基。"Haloalkoxy" means an alkoxy group further composed of from one to the largest possible number of the same or different halo groups, such as fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloro Methoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.
「鹵代烷基 」意指進一步由一至最大可能數目的相同或不同的鹵基組成的烷基,例如氟甲基、三氟甲基、2,2-二氟丙基、氯甲基、三氯甲基、和1,1,2,2-四氟乙基。"Haloalkyl" means an alkyl group further composed of one to the largest possible number of the same or different halo groups, such as fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl Group, and 1,1,2,2-tetrafluoroethyl.
「雜環基 」意指可以是完全飽和、部分不飽和、或完全不飽和的環狀取代基,其中環狀結構含有至少一個碳和至少一個雜原子,其中所述雜原子係氮、硫、或氧。芳香族雜環基的實例包括但不限於:苯并呋喃基、苯并異噻唑基、苯并異㗁唑基、苯并㗁唑基、苯并噻吩基、苯并噻唑基、啉基、呋喃基、吲唑基、吲哚基、咪唑基、異吲哚基、異喹啉基、異噻唑基、異㗁唑基、㗁二唑基、㗁唑啉基、㗁唑基、酞𠯤基、吡𠯤基、吡唑啉基、吡唑基、嗒𠯤基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹㗁啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三𠯤基、和三唑基。完全飽和的雜環基的實例包括但不限於:哌𠯤基、哌啶基、𠰌啉基、吡咯啶基、四氫呋喃基、和四氫哌喃基。部分不飽和的雜環基的實例包括但不限於:1,2,3,4-四氫-喹啉基、4,5-二氫-㗁唑基、4,5-二氫-1H -吡唑基、4,5-二氫-異㗁唑基、和2,3-二氫-[1,3,4]-㗁二唑基。" Heterocyclic group " means a cyclic substituent that can be fully saturated, partially unsaturated, or fully unsaturated, wherein the cyclic structure contains at least one carbon and at least one heteroatom, wherein the heteroatom is nitrogen, sulfur, Or oxygen. Examples of aromatic heterocyclic groups include, but are not limited to: benzofuranyl, benzisothiazolyl, benzisoxazolyl, benzoazolyl, benzothienyl, benzothiazolyl, Linyl, furanyl, indazolyl, indolyl, imidazolyl, isoindolyl, isoquinolinyl, isothiazolyl, isooxazolyl, oxadiazolyl, azolinyl, oxazolyl, Phthaloline, pyrazolyl, pyrazolinyl, pyrazolyl, pyridyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinolinyl, tetrazoline, thiazoline Group, thiazolyl, thienyl, triazolyl, and triazolyl. Examples of fully saturated heterocyclic groups include, but are not limited to: piperidinyl, piperidinyl, pyrolinyl, pyrrolidinyl, tetrahydrofuranyl, and tetrahydropiperanyl. Examples of partially unsaturated heterocyclic groups include, but are not limited to: 1,2,3,4-tetrahydro-quinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1 H- Pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-[1,3,4]-diazolyl.
提供了具有「式一 」之結構的化合物/分子: 式一 Provides compounds/molecules with the structure of "Formula One": Formula one
其中:(A) R1 和R2 各自獨立地選自由以下組成之群組:(F) 、H、C1 -C8 烷基、C1 -C8 鹵代烷基、C2 -C8 烯基、和C2 -C8 炔基,每個係未被取代的或被至少一個R10 取代的;(B) L係C或Si;(C) R3 、R4 、和R5 各自獨立地選自由以下組成之群組:(F) 、H、OH、鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C3 -C6 環烷基、C2 -C6 烯基、C2 -C6 炔基、C1 -C6 烷氧基、C1 -C6 鹵代烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、和C1 -C3 烷基磺醯基,每個係未被取代的或被至少一個R6 取代的;(D) R6 、R7 、R8 、和R9 各自獨立地選自由以下組成之群組:H、OH、氰基、鹵素、C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、C1 -C6 鹵代烷氧基、C2 -C6 烯基、C2 -C6 炔基、C2 -C6 烷基羰基、和C1 -C6 烷基磺醯基,每個係未被取代的或被至少一個R11 取代的;(E) Q係O或S;(F) 視需要R1 、R2 、R3 、R4 、和R5 中任兩個可以連接到烴基連接基A上,以形成3元至7員環結構, 其中該烴基連接基A可以是1員至5員的飽和或不飽和的連接,該連接視需要被一個或多個取代基取代,該取代基獨立地選自C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、或C1 -C6 鹵代烷氧基;(G) R10 各自獨立地是鹵素、氰基、C1 -C3 烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、C1 -C3 烷基磺醯基、或SiRa Rb Rc ; Ra 、Rb 、和Rc 各自獨立地是C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、或C1 -C6 鹵代烷氧基;(H) R11 各自獨立地是鹵素、氰基、C1 -C3 烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、或C1 -C3 烷基磺醯基;以及 該式一 之化合物的農業上可接受的酸加成鹽、鹽衍生物、溶劑化物、酯衍生物、晶體同質異晶物、同位素、拆分的(resoluted)立體異構物、和互變異構物。Wherein: (A) R 1 and R 2 are each independently selected from the group consisting of: (F) , H, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl , And C 2 -C 8 alkynyl, each of which is unsubstituted or substituted with at least one R 10 ; (B) L is C or Si; (C) R 3 , R 4 , and R 5 are each independently Selected from the group consisting of (F) , H, OH, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl , And C 1 -C 3 alkylsulfonyl groups, each of which is unsubstituted or substituted with at least one R 6 ; (D) R 6 , R 7 , R 8 , and R 9 are each independently selected from the following Composition group: H, OH, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkylcarbonyl, and C 1 -C 6 alkylsulfonyl, each of which is unsubstituted or substituted with at least one R 11 ; (E) Q is O or S; (F) any two of R 1 , R 2 , R 3 , R 4 , and R 5 can be connected to the hydrocarbyl linking group A as necessary to form a 3-member to 7-member A ring structure, wherein the hydrocarbyl linking group A may be a saturated or unsaturated link of 1 to 5 members, and the link is optionally substituted by one or more substituents, and the substituents are independently selected from C 1 -C 6 alkanes Group, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, or C 1 -C 6 haloalkoxy; (G) R 10 is each independently halogen, cyano, C 1 -C 3 alkoxy Group, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfinyl, or SiR a R b R c ; R a , R b , and R c each independently is a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a C 1 -C 6 haloalkoxy group; (H) R 11 is each independently a halogen , Cyano, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, or C 1 -C 3 alkylsulfinyl; and the formula one The agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal allomorphs, isotopes, resoluted stereoisomers, and tautomers of the compound.
在一方面,本文提供之化合物具有(A) R1 和R2 各自獨立地是H、C1 -C6 烷基、或C1 -C6 鹵代烷基;(B) L係C;(C) R3 係H、OH、C1 -C3 烷基、C2 -C3 烯基、C1 -C3 鹵代烷基、C2 -C3 鹵代烯基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基; R4 係C1 -C3 烷基、C2 -C3 烯基、C1 -C3 鹵代烷基、C2 -C3 鹵代烯基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基;以及 R5 係H、OH、鹵素、氰基、C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基、C1 -C3 鹵代烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、或C1 -C3 烷基磺醯基;(D) R6 、R7 、R8 、和R9 各自獨立地選自由以下組成之群組:H、OH、氰基、鹵素、C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、和C1 -C6 鹵代烷氧基;(E) Q係O或S;以及 該式一之化合物的農業上可接受的酸加成鹽、溶劑化物、酯、拆分的立體異構物、和互變異構物。In one aspect, the compound provided herein has (A) R 1 and R 2 are each independently H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl; (B) L is C; (C) R 3 is H, OH, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 1 -C 3 haloalkyl, C 2 -C 3 haloalkenyl, C 1 -C 3 alkoxy, Or C 1 -C 3 haloalkoxy; R 4 is C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 1 -C 3 haloalkyl, C 2 -C 3 haloalkenyl, C 1- C 3 alkoxy or C 1 -C 3 haloalkoxy; and R 5 is H, OH, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 Alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, or C 1 -C 3 alkylsulfinyl; (D) R 6 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of H, OH, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, and C 1 -C 6 haloalkoxy; (E) Q is O or S; and agriculturally acceptable acid addition salts, solvates, esters, and resolved compounds of the formula one Stereoisomers, and tautomers.
在另一方面,提供之化合物具有(A) R1 係H;並且R2 係CH3 、CF3 、CH2 CH3 、CF2 CF3 、或CH2 CF3 ;(B) L係C;(C) R3 係H、OH、C1 -C3 烷基、C2 -C3 烯基、C1 -C3 鹵代烷基、C2 -C3 鹵代烯基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基; R4 係C1 -C3 烷基、C2 -C3 烯基、C1 -C3 鹵代烷基、C2 -C3 鹵代烯基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基; R5 係H、OH、鹵素、氰基、C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基、C1 -C3 鹵代烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、或C1 -C3 烷基磺醯基;以及(D) R6 、R8 、和R9 各自獨立地是H、CH3 、CF3 、CH2 CH3 、CF2 CF3 、或CH2 CF3 ;以及 R7 係OH、Cl、Br、I、氰基、CH3 、CF3 、CH2 CH3 、CF2 CF3 、或CH2 CF3 ;以及(E) Q係O;以及 該式一之化合物的農業上可接受的酸加成鹽、溶劑化物、酯、拆分的立體異構物、和互變異構物。In another aspect, the provided compound has (A) R 1 is H; and R 2 is CH 3 , CF 3 , CH 2 CH 3 , CF 2 CF 3 , or CH 2 CF 3 ; (B) L is C; (C) R 3 is H, OH, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 1 -C 3 haloalkyl, C 2 -C 3 haloalkenyl, C 1 -C 3 alkane Oxy, or C 1 -C 3 haloalkoxy; R 4 is C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 1 -C 3 haloalkyl, C 2 -C 3 haloalkenyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy; R 5 is H, OH, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1- C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, or C 1 -C 3 alkylsulfinyl; and ( D) R 6 , R 8 , and R 9 are each independently H, CH 3 , CF 3 , CH 2 CH 3 , CF 2 CF 3 , or CH 2 CF 3 ; and R 7 is OH, Cl, Br, I , Cyano, CH 3 , CF 3 , CH 2 CH 3 , CF 2 CF 3 , or CH 2 CF 3 ; and (E) Q is O; and the agriculturally acceptable acid addition salt of the compound of formula one , Solvates, esters, resolved stereoisomers, and tautomers.
在另一方面,提供之化合物或分子具有下式(「式二 」)的結構: 式二 。In another aspect, the provided compound or molecule has the structure of the following formula (" Formula 2 "): Formula two .
在進一步的方面,提供之化合物具有(A) R1 係H;並且R2 係CH3 、CF3 、CH2 CH3 、CF2 CF3 、或CH2 CF3 ;(C) R3 係H、OH、C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基; R4 係C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基;以及 R5 係H、OH、鹵素、氰基、C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基、或C1 -C3 鹵代烷氧基;以及 該式二之化合物的農業上可接受的酸加成鹽、溶劑化物、酯、拆分的立體異構物、和互變異構物。In a further aspect, the compound provided has (A) R 1 is H; and R 2 is CH 3 , CF 3 , CH 2 CH 3 , CF 2 CF 3 , or CH 2 CF 3 ; (C) R 3 is H , OH, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy; R 4 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy; and R 5 is H, OH, halogen, cyano, C 1 -C 3 alkyl, C 1- C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy; and the agriculturally acceptable acid addition salt, solvate, ester, and resolved stereo of the compound of formula II Isomers, and tautomers.
在另一方面,提供的化合物具有選自在表1中所列出之化合物的結構。In another aspect, the provided compound has a structure selected from the compounds listed in Table 1.
在另一方面,提供的化合物具有以下結構之一:或。In another aspect, the provided compound has one of the following structures: or .
還提供了組成物,其包含殺線蟲有效量之如請求項1所述之化合物和至少一種選自由表面活性劑、固體稀釋劑、和液體稀釋劑組成之群組的額外組分。A composition is also provided, which comprises a nematicidally effective amount of the compound as described in claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.
在一方面,提供的組成物進一步包含至少一種額外的生物學活性化合物或藥劑。In one aspect, the provided composition further comprises at least one additional biologically active compound or agent.
在進一步的方面,該至少一種額外的生物學活性化合物或藥劑選自由以下組成之群組:三氟咪啶醯胺(fluazaindolizine)、阿巴美丁(abamectin)、高滅磷(acephate)、滅蟎醌(acequinocyl)、啶蟲脒(acetamiprid)、氟丙菊酯(acrinathrin)、啶喃環丙蟲酯(afidopyropen)、磺胺蟎酯(amidoflumet)、雙甲脒(amitraz)、阿維菌素(avermectin)、印楝素(azadirachtin)、穀硫磷(azinphos-methyl)、丙硫克百威(benfuracarb)、殺蟲磺(bensultap)、聯苯菊酯(bifenthrin)、聯苯肼酯(bifenazate)、雙三氟蟲脲(bistrifluron)、硼酸鹽(borate)、噻𠯤酮(buprofezin)、硫線磷(cadusafos)、西維因(carbaryl)、卡巴呋喃(carbofuran)、殺螟丹(cartap)、伐蟲脒(carzol)、氯蟲苯甲醯胺(chlorantraniliprole)、溴蟲腈(chlorfenapyr)、定蟲隆(chlorfluazuron)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、環蟲醯肼(chromafenozide)、蟎死淨(clofentezin)、噻蟲胺(clothianidin)、氰蟲醯胺(cyantraniliprole)、環溴蟲醯胺(cyclaniliprole)、乙氰菊酯(cycloprothrin)、環氧蟲啶(cycloxaprid)、丁氟蟎酯(cyflumetofen)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、ζ-氯氰菊酯(zeta-cypermethrin)、滅蠅胺(cyromazine)、溴氰菊酯(deltamethrin)、丁醚脲(diafenthiuron)、二𠯤農(diazinon)、狄氏劑(dieldrin)、二氟脲(diflubenzuron)、四氟甲醚菊酯(dimefluthrin)、殺蟲雙(dimehypo)、樂果(dimethoate)、呋蟲胺(dinotefuran)、苯蟲醚(diofenolan)、艾瑪菌素(emamectin)、安殺番(endosulfan)、高氰戊菊酯(esfenvalerate)、乙蟲腈(ethiprole)、依芬普司(etofenprox)、乙蟎唑(etoxazole)、苯丁錫(fenbutatin oxide)、殺螟硫磷(fenitrothion)、苯硫威(fenothiocarb)、苯氧威(fenoxycarb)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟蟲腈(fipronil)、氟甲氧喹啉(flometoquin)、氟啶蟲醯胺(flonicamid)、氟蟲醯胺(flubendiamide)、氟氰戊菊酯(flucythrinate)、嘧蟲胺(flufenerim)、氟蟲脲(flufenoxuron)、氟菌蟎酯(flufenoxystrobin)、聯氟碸(fluensulfone)、氟吡菌醯胺(fluopyram)、氟吡呋喃酮(flupyradifurone)、氟胺氰菊酯(fluvalinate)、τ-氟胺氰菊酯(tau-fluvalinate)、地蟲硫磷(fonophos)、伐蟲脒(formetanate)、噻唑磷(fosthiazate)、氯蟲醯肼(halofenozide)、右旋七氟甲醚菊酯(heptafluthrin)、氟鈴脲(hexaflumuron)、噻蟎酮(hexythiazox)、氟蟻腙(hydramethylnon)、吡蟲啉(imidacloprid)、茚蟲威(indoxacarb)、殺蟲皂(insecticidal soaps)、異柳磷(isofenphos)、虱蟎脲(lufenuron)、馬拉硫磷(malathion)、氯氟醚菊酯(meperfluthrin)、氰氟蟲腙(metaflumizone)、蝸牛敵(metaldehyde)、甲胺磷(methamidophos)、殺撲磷(methidathion)、滅蟲威、(methiocarb)、滅多蟲(methomyl)、甲氧普林(methoprene)、甲氧滴滴涕(methoxychlor)、甲氧蟲醯肼(methoxyfenozide)、甲氧苄氟菊酯(metofluthrin)、久效磷(monocrotophos)、單氟醚菊酯(monofluorothrin)、菸鹼(nicotine)、烯啶蟲胺(nitenpyram)、硝乙脲噻唑(nithiazine)、雙苯氟脲(novaluron)、多氟脲(noviflumuron)、草胺醯(oxamyl)、對硫磷(parathion)、甲基對硫磷(parathion-methyl)、撲滅司林(permethrin)、甲拌磷(phorate)、伏殺硫磷(phosalone)、亞胺硫磷(phosmet)、磷胺(phosphamidon)、抗蚜威(pirimicarb)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、克蟎特(propargite)、丙苯烴菊酯(protrifenbute)、吡氟丁醯胺(pyflubumide)、吡蚜酮(pymetrozine)、吡𠯤氟蟲腈(pyrafluprole)、除蟲菊酯(pyrethrin)、嗒蟎靈(pyridaben)、啶蟲丙醚(pyridalyl)、新喹唑啉(間二氮雜苯)類殺蟲劑(pyrifluquinazon)、嘧蟎胺(pyriminostrobin)、吡啶氟蟲腈(pyriprole)、蚊蠅醚(pyriproxyfen)、魚藤酮(rotenone)、利阿諾定(ryanodine)、氟矽菊酯(silafluofen)、乙基多殺菌素(spinetoram)、多殺菌素(spinosad)、螺蟎酯(spirodiclofen)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、硫丙磷(sulprofos)、碸蟲啶(sulfoxaflor)、蟲醯肼(tebufenozide)、吡蟎胺(tebufenpyrad)、伏蟲脲(teflubenzuron)、七氟菊酯(tefluthrin)、特丁磷(terbufos)、殺蟲畏(tetrachlorvinphos)、似蟲菊(tetramethrin)、四氟醚菊酯(tetramethylfluthrin)、噻蟲啉(thiacloprid)、噻蟲𠯤(thiamethoxam)、硫雙威(thiodicarb)、殺蟲雙(thiosultap-sodium)、噻㗁唑碸(tioxazafen)、唑蟲醯胺(tolfenpyrad)、四溴菊酯(tralomethrin)、唑蚜威(triazamate)、敵百蟲(trichlorfon)、三氟苯嘧啶(triflumezopyrim)、殺蟲隆(triflumuron)、蘇力菌-δ內毒素、昆蟲病原細菌(entomopathogenic bacteria)、昆蟲病原病毒(entomopathogenic viruse)、以及昆蟲病原真菌。In a further aspect, the at least one additional biologically active compound or agent is selected from the group consisting of fluazaindolizine, abamectin, acephate, Acequinocyl, acetamiprid, acrinathrin, afidopyropen, amidoflumet, amitraz, abamectin avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate , Bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, Carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chlorpyrifos-methyl, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cycloxaprid, Cyflumetofen, Cyfluthrin, Beta-cyfluthrin, Cyhalothrin, Gamma-cyhalothrin, Lambda-cyhalothrin, Lambda-cyhalothrin cyhalothrin, cypermethrin, alpha-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, diafenthiuron, difenthiuron Agriculture (diazinon), dieldrin (dieldrin), diflubenzuron (diflubenzuron) , Dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, dimehypo endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenitrothion, Fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, floxifloxacin Amine (flonicamid), flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, fluensulfone , Fluopyram (fluopyram), flupyradifurone (flupyradifurone), fluvalinate (fluvalinate), tau-fluvalinate (tau-fluvalinate), fonophos (fonophos), valworm Formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon ), imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, cyfluthrin ( meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene methoprene), methoxychlor, methoxyfenozide, metofluthrin (metofluthrin) thrin), monocrotophos, monofluorothrin, nicotine, nitenpyram, nithiazine, novaluron, and more Fluorourea (noviflumuron), oxamyl (oxamyl), parathion (parathion), methyl parathion (parathion-methyl), permethrin (permethrin), phorate (phorate), sulfonate ( phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, pyrethrum Esters (protrifenbute), pyflubumide (pyflubumide), pymetrozine (pymetrozine), pyrafluprole (pyrafluprole), pyrethrin (pyrethrin), pyridaben (pyridaben), acetamiprid ( pyridalyl), new quinazoline (m-diazepine) insecticides (pyrifluquinazon), pyriminostrobin, pyriprole, pyriproxyfen, rotenone, Ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spiromesifen (Spirotetramat), sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos (Terbufos), tetrachlorvinphos, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, insecticide Bis (thiosultap-sodium), thiazole (tioxazafen), tolfenpyrad (tolfenpyrad), permethrin (tralomethrin), triapyr (tria zamate), trichlorfon, triflumezopyrim, triflumuron, threnia-delta endotoxin, entomopathogenic bacteria, entomopathogenic viruse, and Entomopathogenic fungi.
在另一方面,至少一種額外的生物學活性化合物或藥劑選自由以下組成之群組:三氟咪啶醯胺(fluazaindolizine)、阿巴美丁、啶蟲脒、氟丙菊酯、啶喃環丙蟲酯、雙甲脒、阿維菌素、印楝素、丙硫克百威、殺蟲磺、聯苯菊酯、噻𠯤酮、硫線磷、西維因、殺螟丹、氯蟲苯甲醯胺、溴蟲腈、毒死蜱、噻蟲胺、氰蟲醯胺、環溴蟲醯胺、乙氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、γ-三氟氯氰菊酯、λ-三氟氯氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、滅蠅胺、溴氰菊酯、狄氏劑、呋蟲胺、苯蟲醚、艾瑪菌素、安殺番、高氰戊菊酯、乙蟲腈、依芬普司、乙蟎唑、殺螟硫磷、苯硫威、苯氧威、氰戊菊酯、氟蟲腈、氟甲氧喹啉(flometoquin)、氟啶蟲醯胺、氟蟲醯胺、氟蟲脲、氟菌蟎酯、聯氟碸、flupiprole、氟吡呋喃酮、氟胺氰菊酯、伐蟲脒、噻唑磷、右旋七氟甲醚菊酯(heptafluthrin)、氟鈴脲、氟蟻腙、吡蟲啉、茚蟲威、虱蟎脲、氯氟醚菊酯、氰氟蟲腙、甲硫雙威、滅多蟲、甲氧普林、甲氧蟲醯肼、甲氧苄氟菊酯、單氟醚菊酯(monofluorothrin)、烯啶蟲胺、硝乙脲噻唑、雙苯氟脲、草胺醯、吡氟丁醯胺(pyflubumide)、吡蚜酮、除蟲菊酯、嗒蟎靈、啶蟲丙醚、嘧蟎胺、蚊蠅醚、利阿諾定、乙基多殺菌素、多殺菌素、螺蟎酯、螺甲蟎酯、螺蟲乙酯、碸蟲啶、蟲醯肼、似蟲菊、四氟醚菊酯、噻蟲啉、噻蟲𠯤、硫雙威、殺蟲雙、四溴菊酯、唑蚜威、三氟苯嘧啶、殺蟲隆、蘇力菌δ-內毒素、蘇力菌的所有菌株以及核型多角體病毒的所有毒株。In another aspect, the at least one additional biologically active compound or agent is selected from the group consisting of: fluazaindolizine, abamectin, acetamiprid, flumethrin, pyridine pyridine Propiprofen, diformamidine, abamectin, azadirachtin, benfuracarb, difenthrin, bifenthrin, thienone, thionifos, carbaryl, salamidine, chlorfenarum Benzamide, chlorfenapyr, chlorpyrifos, clothianidin, cyanidan, chlorfenapyr, cyfluthrin, cyfluthrin, β-cyfluthrin, cyfluthrin, γ-cyfluthrin, λ -Cyfluthrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, fenfenpyr, emamectin, fenvalerate, fenvalerate , Ethiprole, efenprox, etoxazole, fenthiophos, fenthiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin (flometoquin), flufenoxamide , Sulfipramide, flufenoxuron, flufenoxamate, diflufenazone, flupiprole, flupyridone, fluvalinate, valfenamidine, thiazophos, heptafluthrin (heptafluthrin) , Hexaflumuron, fenflurhydrazone, imidacloprid, indoxacarb, lufenuron, cyfluthrin, cyflufenox, thiodicarb, metdopyr, methoprene, methoprene, meth Perfluthrin, monofluorothrin, nitenpyram, nithiazole, diflubenzuron, chlorambucil, pyflubumide (pyflubumide), pymetrozine, pyrethrum Ester, Tamifen, Acetamiprid, Pyramid, Cyclofen, Rianodine, Spinetoram, Spinosyn, Spirodicofen, Spiromethiconin, Spirotetramat, Suspension Pyridine, fenflurazine, pyrethrum, perfluthrin, thiacloprid, clothianid, thiodicarb, dimehypo, permethrin, triflucarb, trifluoropyrimidine, triflubenzuron, Surinea delta-endotoxin, all strains of Suricata, and all strains of nuclear polyhedrosis virus.
還提供了用於控制土壤棲息線蟲之方法,該方法包括使線蟲或其環境與生物學有效量之具有式一 之結構的化合物接觸: 式一 A method for controlling soil-inhabited nematodes is also provided, the method comprising contacting the nematodes or their environment with a biologically effective amount of a compound having the structure of Formula 1: Formula one
其中:(A) R1 和R2 各自獨立地選自由以下組成之群組:(F) 、H、C1 -C8 烷基、C1 -C8 鹵代烷基、C2 -C8 烯基、和C2 -C8 炔基,每個係未被取代的或被至少一個R10 取代的;(B) L係C或Si;(C) R3 、R4 、和R5 各自獨立地選自由以下組成之群組:(F) 、H、OH、鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C3 -C6 環烷基、C2 -C6 烯基、C2 -C6 炔基、C1 -C6 烷氧基、C1 -C6 鹵代烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、和C1 -C3 烷基磺醯基,每個係未被取代的或被至少一個R6 取代的;(D) R6 、R7 、R8 、和R9 各自獨立地選自由以下組成之群組:H、OH、氰基、鹵素、C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、C1 -C6 鹵代烷氧基、C2 -C6 烯基、C2 -C6 炔基、C2 -C6 烷基羰基、和C1 -C6 烷基磺醯基,每個係未被取代的或被至少一個R11 取代的;(E) Q係O或S;(F) 視需要R1 、R2 、R3 、R4 、和R5 中任兩個可以連接到烴基連接基A上,以形成3員至7員環結構, 其中該烴基連接基A可以是1員至5員的飽和或不飽和的連接,該連接視需要被一個或多個取代基取代,該取代基獨立地選自C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、或C1 -C6 鹵代烷氧基;(G) R10 各自獨立地是鹵素、氰基、C1 -C3 烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、C1 -C3 烷基磺醯基、或SiRa Rb Rc ; Ra 、Rb 、和Rc 各自獨立地是C1 -C6 烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷基、或C1 -C6 鹵代烷氧基;(H) R11 各自獨立地是鹵素、氰基、C1 -C3 烷氧基、C1 -C3 烷硫基、C1 -C3 烷基亞磺醯基、或C1 -C3 烷基磺醯基;以及 該式一 之化合物的農業上可接受的酸加成鹽、鹽衍生物、溶劑化物、酯衍生物、晶體同質異晶物、同位素、拆分的立體異構物、和互變異構物。Wherein: (A) R 1 and R 2 are each independently selected from the group consisting of: (F) , H, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl , And C 2 -C 8 alkynyl, each of which is unsubstituted or substituted with at least one R 10 ; (B) L is C or Si; (C) R 3 , R 4 , and R 5 are each independently Selected from the group consisting of (F) , H, OH, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl , And C 1 -C 3 alkylsulfonyl groups, each of which is unsubstituted or substituted with at least one R 6 ; (D) R 6 , R 7 , R 8 , and R 9 are each independently selected from the following Composition group: H, OH, cyano, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkylcarbonyl, and C 1 -C 6 alkylsulfonyl, each of which is unsubstituted or substituted with at least one R 11 ; (E) Q is O or S; (F) any two of R 1 , R 2 , R 3 , R 4 , and R 5 can be connected to the hydrocarbyl linking group A as necessary to form 3 to 7 members A ring structure, wherein the hydrocarbyl linking group A may be a saturated or unsaturated link of 1 to 5 members, and the link is optionally substituted by one or more substituents, and the substituents are independently selected from C 1 -C 6 alkanes Group, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, or C 1 -C 6 haloalkoxy; (G) R 10 is each independently halogen, cyano, C 1 -C 3 alkoxy Group, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfinyl, or SiR a R b R c ; R a , R b , and R c each independently is a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a C 1 -C 6 haloalkoxy group; (H) R 11 is each independently a halogen , Cyano, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, or C 1 -C 3 alkylsulfinyl; and the formula one Agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal allomorphs, isotopes, resolved stereoisomers, and tautomers of the compounds.
在一方面,該環境包含植物。在進一步的實施方式中,該植物為作物植物。In one aspect, the environment contains plants. In a further embodiment, the plant is a crop plant.
在另一方面,該環境包含種子。在進一步的方面,該種子用式一 之化合物進行包衣,該化合物被配製成包含成膜劑或黏合劑的組成物。In another aspect, the environment contains seeds. In a further aspect, the seed is coated with a compound of Formula 1 , and the compound is formulated into a composition containing a film-forming agent or a binder.
還提供了用於控制土壤棲息線蟲之方法,該方法包括使線蟲或其環境與生物學有效量之本文提供的組成物接觸。Also provided is a method for controlling soil-inhabited nematodes, the method comprising contacting the nematodes or their environment with a biologically effective amount of the composition provided herein.
合成synthesis
如方案1和2中描述的以下方法和變型中的一種或多種可用於製備式一 之化合物。除非另有注釋,以下取代基的定義如上所定義的。室溫在約20°C至25°C之間。One or more of the following methods and variants as described in Schemes 1 and 2 can be used to prepare the compound of formula one. Unless otherwise noted, the definitions of the following substituents are as defined above. The room temperature is between about 20°C and 25°C.
式一 之化合物可藉由式3 之化合物(其中LG係脫離基,例如鹵素)與式4 的胺(如方案1中所示)的反應製備。當LG係鹵素時,反應通常在鹼存在下和在合適的溶劑中進行。合適的鹼包括胺,如三乙胺、吡啶和甲基吡啶、無機金屬鹽,如碳酸鹽、碳酸氫鹽、氫氧化物和醇鹽,包括碳酸鈉和碳酸鉀、碳酸氫鈉和碳酸氫鉀、氫氧化鈉和乙醇鈉。合適溶劑的選擇取決於LG的性質、鹼和選擇的反應條件。典型的溶劑包括脂族烴如己烷、環己烷和庚烷,芳烴如甲苯和二甲苯,鹵代烴如二氯甲烷、二氯乙烷和氯苯,醚如乙醚、四氫呋喃、二㗁𠮿和二甲氧基乙烷,酯如乙酸乙酯,醯胺例如N,N -二甲基甲醯胺(DMF)、N,N-二甲基乙醯胺(DMAC)和N-甲基吡咯啶酮,腈類如乙腈,酮類如丙酮和甲基乙基酮(MEK),和極性質子溶劑如乙醇和水。方案 1 The compound of formula 1 can be prepared by the reaction of the compound of formula 3 (where LG is leaving the group, such as halogen) and the amine of formula 4 (as shown in Scheme 1). When LG is a halogen, the reaction is usually carried out in the presence of a base and in a suitable solvent. Suitable bases include amines such as triethylamine, pyridine and picoline, inorganic metal salts such as carbonates, bicarbonates, hydroxides and alkoxides, including sodium and potassium carbonate, sodium bicarbonate and potassium bicarbonate , Sodium hydroxide and sodium ethoxide. The choice of a suitable solvent depends on the nature of LG, the base and the selected reaction conditions. Typical solvents include aliphatic hydrocarbons such as hexane, cyclohexane and heptane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane and chlorobenzene, and ethers such as diethyl ether, tetrahydrofuran and diethyl ether. And dimethoxyethane, esters such as ethyl acetate, amides such as N,N -dimethylformamide (DMF), N,N-dimethylacetamide (DMAC) and N-methylpyrrole Pyridones, nitriles such as acetonitrile, ketones such as acetone and methyl ethyl ketone (MEK), and polar protic solvents such as ethanol and water. Scheme 1
式一 之化合物還可藉由式5 之化合物與式4 的胺(如方案2中所示)的反應製備。在該方法中,使用了醯胺偶合試劑如HATU(1-[雙(二甲基胺基)亞甲基]-1H -1,2,3-三唑并[4,5-b ]吡啶陽離子3-氧化物六氟磷酸酯)、EDC(1-乙基-3-(3-二甲基胺基丙基)碳二亞胺)、或T3P(2,4,6-三丙基-1,3,5,2,4,6-三氧雜三磷酸-2,4,6-三氧化物)。該等醯胺偶合的反應條件是本領域已知的。方案 2 Prepared by reaction of a compound of the formula a compound of formula 5 may also be by an amine of the formula (as shown in Scheme 2) 4. In this method, an amide coupling reagent such as HATU (1-[bis(dimethylamino)methylene]-1 H -1,2,3-triazolo[4,5- b ]pyridine Cationic 3-oxide hexafluorophosphate), EDC (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide), or T3P (2,4,6-tripropyl- 1,3,5,2,4,6-trioxatriphosphate-2,4,6-trioxide). The reaction conditions for the coupling of these amides are known in the art. Scheme 2
式一 之化合物(其中R4 不是H)也可以由它們各自的類似物(其中R4 係H),藉由與適當取代的烷基、醯基或其他試劑反應製備。Compounds of formula 1 (wherein R 4 is not H) can also be prepared from their respective analogs (wherein R 4 is H) by reacting with appropriately substituted alkyl, acyl or other reagents.
應認識到,上述對於製備式一 之化合物所描述的某些試劑和反應條件可能不與中間體中存在的某些官能基相容。在該等情況下,將保護/去保護序列或官能基相互轉換結合到合成中將有助於獲得所期望的產物。保護基團的使用和選擇對於化學合成領域的技術者將是顯而易見的(參見,例如Greene,T.W.;Wuts, P. G. M.Protective Groups in Organic Synthesis [有機合成中的保護基團], 第2版; Wiley: 紐約, 1991)。熟悉該項技術者將認識到,在一些情況下,在按照任何單獨方案中描繪的引入給定試劑後,可能需要進行沒有詳細描述的額外的常規合成步驟以完成式一 之化合物的合成。熟悉該項技術者還將認識到,可能需要以與製備式一 之化合物所呈現的具體序列不同的順序來進行以上方案中示出的步驟的組合。It should be recognized that certain reagents and reaction conditions described above for the preparation of the compound of Formula One may not be compatible with certain functional groups present in the intermediate. In these cases, the incorporation of protection/deprotection sequences or functional groups into the synthesis will help to obtain the desired product. The use and choice of protecting groups will be obvious to those skilled in the field of chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis [protecting groups in organic synthesis], 2nd edition; Wiley: New York, 1991). Those skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may require additional routine synthetic steps not described in detail to complete the synthesis of compounds of formula a. Those skilled in the art will also recognize that it may be necessary to perform the combination of steps shown in the above scheme in a different order than the specific sequence presented in the preparation of the compound of Formula One.
熟悉該項技術者還將認識到,本文所述之式一 之化合物和中間體可經受各種親電反應、親核反應、自由基反應、有機金屬反應、氧化反應和還原反應以添加取代基或改性現有的取代基。實例 Those familiar with the technology will also recognize that the compounds and intermediates of Formula One described herein can undergo various electrophilic reactions, nucleophilic reactions, free radical reactions, organometallic reactions, oxidation reactions, and reduction reactions to add substituents or modify The existing substituents. Instance
該等實例是為了說明的目的,而不應被解釋為將本揭露局限於在該等實例中所揭露之實施方式。These examples are for illustrative purposes and should not be construed as limiting the disclosure to the implementations disclosed in these examples.
在無需進一步純化的情況下,使用從商業來源獲得的起始材料、試劑、和溶劑。無水溶劑作為Sure/Seal™購買自奧爾德里奇公司(Aldrich)並且按原樣使用。在Thomas Hoover Unimelt毛細管熔點測定儀或來自斯坦福研究系統(Stanford Research Systems)的OptiMelt自動熔點系統上獲得熔點,並且不校正。採用「室溫(或rt)」的實例係在溫度處於約20°C至約24°C範圍內的氣候控制實驗室中進行。分子被給予它們已知的名稱,根據ChemDraw、或ACD/Name中的命名程式命名。如果此類程式不能命名分子,則使用常規命名規則命名此類分子。1 H NMR光譜數據按ppm (δ) 計並且在400、或500 MHz記錄,並且13 C NMR光譜數據按ppm (δ) 計並且在100或126 MHz記錄,除非另行說明。實例 1 : (S )-3- 氯 -N -(3,3- 二甲基丁 -2- 基 ) 吡 𠯤 -2- 甲醯胺 (A1) 的製備 Where no further purification is required, starting materials, reagents, and solvents obtained from commercial sources are used. The anhydrous solvent was purchased from Aldrich as Sure/Seal™ and used as it is. The melting point is obtained on the Thomas Hoover Unimelt capillary melting point analyzer or the OptiMelt automatic melting point system from Stanford Research Systems, and is not corrected. The example using "room temperature (or rt)" is performed in a climate control laboratory with a temperature in the range of about 20°C to about 24°C. Molecules are given their known names and are named according to the naming program in ChemDraw or ACD/Name. If such programs cannot name molecules, use conventional naming rules to name such molecules. 1 H NMR spectral data is in ppm (δ) and recorded at 400, or 500 MHz, and 13 C NMR spectral data is in ppm (δ) and recorded at 100 or 126 MHz, unless otherwise specified. Example 1 : Preparation of ( S )-3 -chloro - N -(3,3 -dimethylbut -2- yl ) pyridine -2 - methanamide (A1)
將無水DMF(3 mL)中的3-氯-2-吡𠯤-甲酸(100 mg,0.63 mmol)、1-[雙(二甲基胺基)亞甲基]-1H -1,2,3-三唑并[4,5-b ]吡啶陽離子3-氧化物六氟磷酸酯(HATU;360 mg,0.95 mmol)、(S )-3,3-二甲基丁-2-胺(103 μL,0.76 mmol)、和N -乙基二異丙基胺(220 μL,1.26 mmol)的溶液在室溫下攪拌過夜。在真空下去除溶劑並且將殘餘物溶解於二氯甲烷(25 mL)中。將有機層用鹽水洗滌(3 x 10 mL),經硫酸鈉乾燥,並且濃縮。藉由快速柱層析法進行純化,得到呈白色固體的標題化合物(65 mg,41%):mp 143°C-145°C;1 H NMR (500 MHz, DMSO-d 6 ) δ 8.68 (d,J = 2.5 Hz, 1H), 8.60 (d,J = 2.5 Hz, 1H), 8.44 (d,J = 9.5 Hz, 1H), 3.88 (dq,J = 9.6, 6.9 Hz, 1H), 1.07 (d,J = 6.9 Hz, 3H), 0.92 (s, 9H);13 C NMR (126 MHz, DMSO-d 6 ) δ 163.84, 150.18, 145.16, 145.09, 143.00, 53.06, 34.90, 26.65, 15.98。ESIMSm/z 242[(M+H)+]Mix 3-chloro-2-pyridine-carboxylic acid (100 mg, 0.63 mmol) and 1-[bis(dimethylamino)methylene]-1 H -1,2, in anhydrous DMF (3 mL) 3-triazolo[4,5- b ]pyridine cation 3-oxide hexafluorophosphate (HATU; 360 mg, 0.95 mmol), ( S )-3,3-dimethylbutan-2-amine (103 A solution of μL, 0.76 mmol), and N -ethyldiisopropylamine (220 μL, 1.26 mmol) was stirred overnight at room temperature. The solvent was removed under vacuum and the residue was dissolved in dichloromethane (25 mL). The organic layer was washed with brine (3 x 10 mL), dried over sodium sulfate, and concentrated. Purification by flash column chromatography gave the title compound (65 mg, 41%) as a white solid: mp 143°C-145°C; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.68 (d , J = 2.5 Hz, 1H), 8.60 (d, J = 2.5 Hz, 1H), 8.44 (d, J = 9.5 Hz, 1H), 3.88 (dq, J = 9.6, 6.9 Hz, 1H), 1.07 (d , J = 6.9 Hz, 3H), 0.92 (s, 9H); 13 C NMR (126 MHz, DMSO- d 6 ) δ 163.84, 150.18, 145.16, 145.09, 143.00, 53.06, 34.90, 26.65, 15.98. ESIMS m/z 242[(M+H)+]
依照實例 1 中的程序製備以下化合物。 (R )-3- 氯 -N -(3,3- 二甲基丁 -2- 基 ) 吡 𠯤 -2- 甲醯胺( A2 ) The following compounds were prepared according to the procedure in Example 1. (R) -3- chloro - N - (3,3- dimethyl-2-yl) -2-pyrazole 𠯤 Amides (A2)
分離出呈白色固體的標題化合物(245 mg,61%):1 H NMR (500 MHz, 三氯甲烷-d ) δ 8.53 (d,J = 2.4 Hz, 1H), 8.49 (d,J = 2.3 Hz, 1H), 7.51 - 7.41 (m, 1H), 4.07 (dq,J = 9.8, 6.8 Hz, 1H), 1.19 (d,J = 6.9 Hz, 3H), 0.98 (s, 9H)。The title compound (245 mg, 61%) was isolated as a white solid: 1 H NMR (500 MHz, chloroform- d ) δ 8.53 (d, J = 2.4 Hz, 1H), 8.49 (d, J = 2.3 Hz , 1H), 7.51-7.41 (m, 1H), 4.07 (dq, J = 9.8, 6.8 Hz, 1H), 1.19 (d, J = 6.9 Hz, 3H), 0.98 (s, 9H).
13 C NMR (126 MHz, 三氯甲烷-d ) δ 161.35, 148.33, 145.50, 143.70, 140.60, 53.31, 34.48, 26.25, 16.02。ESIMSm/z 242[(M+H)+]3- 氯 -N -(3,3- 二甲基丁 -2- 基 ) 吡 𠯤 -2- 甲醯胺( A3 ) 13 C NMR (126 MHz, chloroform- d ) δ 161.35, 148.33, 145.50, 143.70, 140.60, 53.31, 34.48, 26.25, 16.02. ESIMS m/z 242[(M+H)+] 3- Chloro- N -(3,3 -dimethylbut -2- yl ) pyridine -2 - methanamide (A3 )
分離出呈白色固體的標題化合物(292 mg,73%):1H NMR (500 MHz, 三氯甲烷-d ) δ 8.53 (d,J = 2.3 Hz, 1H), 8.49 (d,J = 2.3 Hz, 1H), 7.52 - 7.38 (m, 1H), 4.07 (dq,J = 9.9, 6.8 Hz, 1H), 1.19 (d,J = 6.8 Hz, 3H), 0.98 (s, 9H)。The title compound (292 mg, 73%) was isolated as a white solid: 1H NMR (500 MHz, chloroform- d ) δ 8.53 (d, J = 2.3 Hz, 1H), 8.49 (d, J = 2.3 Hz, 1H), 7.52-7.38 (m, 1H), 4.07 (dq, J = 9.9, 6.8 Hz, 1H), 1.19 (d, J = 6.8 Hz, 3H), 0.98 (s, 9H).
13 C NMR (126 MHz, 三氯甲烷-d ) δ 161.35, 148.37, 145.50, 143.69, 140.59, 53.31, 34.49, 26.25, 16.03。ESIMSm/z 242[(M+H)+]實例 2 : (S )-3- 氯 -N -(3- 乙基戊 -2- 基 ) 吡 𠯤 -2- 甲醯胺 (A4) 的製備 13 C NMR (126 MHz, chloroform- d ) δ 161.35, 148.37, 145.50, 143.69, 140.59, 53.31, 34.49, 26.25, 16.03. Preparation of (3-ethyl-2-yl) -2-pyrazole 𠯤 Amides (A4) a - N - (S) -3- chloro-: 242 [(M + H) +] Example 2 ESIMS m / z
經由注射器向乙酸乙酯(5 mL)中的3-氯吡𠯤-2-甲酸(200 mg,1.26 mmol)的冰冷溶液中滴加N -甲基𠰌啉(NMM;555 µL,5.05 mmol)、(S )-3-乙基戊-2-氯化銨(C3 ;191 mg,1.26 mmol)、和2,4,6-三丙基-1,3,5,2,4,6-三氧雜三磷酸2,4,6-三氧化物(T3P;751 µL,2.52 mmol)。去除冰浴,並且允許反應混合物在室溫下攪拌過夜。將反應混合物用乙酸乙酯(10 mL)稀釋,並且用水洗滌(3 x 10 mL),經硫酸鈉乾燥,並且濃縮。藉由柱層析法純化(使用己烷和乙酸乙酯-乙醇(3 : 1))得到呈白色固體的標題化合物(157 mg,46%):1 H NMR (500 MHz, CDCl3 ) δ 8.53 (d,J = 2.3 Hz, 1H), 8.48 (d,J = 2.3 Hz, 1H), 7.47 (d,J = 9.3 Hz, 1H), 4.35 - 4.26 (m, 1H), 1.49 - 1.31 (m, 5H), 1.21 (d,J = 6.8 Hz, 3H), 0.96 (dt,J = 10.1, 6.9 Hz, 6H);13 C NMR (126 MHz, CDCl3 ) δ 161.25, 148.32, 145.50, 143.55, 140.56, 46.83, 46.03, 22.19, 22.14, 17.50, 11.83, 11.63;ESIMSm/z 256 ([M+H]+ )。實例 3 : (S )-3- 氯 -N -(1-( 三甲基矽基 ) 丙 -2- 基 ) 吡 𠯤 -2- 甲醯胺 (A5) 的製備 To the ice-cold solution of 3-chloropyridine-2-carboxylic acid (200 mg, 1.26 mmol) in ethyl acetate (5 mL) via a syringe was added dropwise N -methyl pyridine (NMM; 555 µL, 5.05 mmol), ( S )-3-ethylpentan-2-ammonium chloride ( C3 ; 191 mg, 1.26 mmol), and 2,4,6-tripropyl-1,3,5,2,4,6-trioxo Heterotriphosphate 2,4,6-trioxide (T3P; 751 µL, 2.52 mmol). The ice bath was removed, and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with water (3 x 10 mL), dried over sodium sulfate, and concentrated. Purification by column chromatography (using hexane and ethyl acetate-ethanol (3:1)) gave the title compound (157 mg, 46%) as a white solid: 1 H NMR (500 MHz, CDCl 3 ) δ 8.53 (d, J = 2.3 Hz, 1H), 8.48 (d, J = 2.3 Hz, 1H), 7.47 (d, J = 9.3 Hz, 1H), 4.35-4.26 (m, 1H), 1.49-1.31 (m, 5H), 1.21 (d, J = 6.8 Hz, 3H), 0.96 (dt, J = 10.1, 6.9 Hz, 6H); 13 C NMR (126 MHz, CDCl 3 ) δ 161.25, 148.32, 145.50, 143.55, 140.56, 46.83, 46.03, 22.19, 22.14, 17.50, 11.83, 11.63; ESIMS m/z 256 ([M+H] + ). Example 3: (S) -3- chloro - Preparation of (1- (trimethyl silicon based) propan-2-yl) -2-pyrazole 𠯤 Amides (A5) is - N
將無水DMF(3 mL)中的3-氯-2-吡𠯤-甲酸(200 mg,1.26 mmol)、HATU(720 mg,1.89 mmol)、(S )-1-(三甲基矽基)丙-2-氯化銨(C6 ;212 mg,1.26 mmol)、和N -乙基二異丙基胺(441 μL,2.52 mmol)溶液在室溫下攪拌過夜。在真空下去除溶劑並且將殘餘物溶解於二氯甲烷(25 mL)中。將有機層用鹽水洗滌(3 x 10 mL),經硫酸鈉乾燥,並且濃縮。藉由快速柱層析法純化(使用己烷和乙酸乙酯-乙醇(3 : 1))得到呈白色固體的標題化合物(242 mg,67%):1 H NMR (500 MHz, CDCl3 ) δ 8.52 (d,J = 2.3 Hz, 1H), 8.47 (d,J = 2.3 Hz, 1H), 7.41 (d,J = 6.7 Hz, 1H), 4.30 (tt,J = 8.2, 6.6 Hz, 1H), 1.31 (d,J = 6.5 Hz, 3H), 1.04 (dd,J = 14.5, 6.7 Hz, 1H), 0.89 (dd,J = 14.5, 8.0 Hz, 1H), 0.07 (s, 9H);13 C NMR (126 MHz, CDCl3 ) δ 160.63, 148.28, 145.44, 143.42, 140.47, 43.61, 25.84, 23.99, -0.93。ESIMSm/z 270 ([M-H]- )。中間體的合成 實例 4 : (S )-3- 乙基戊 -2- 氯化銨 (C3) 的製備 步驟 1 - (R ,Z )-N -(3- 乙基戊 -2- 基亞基 )-2- 甲基丙烷 -2- 亞磺醯胺 (C1) 的製備 Add 3-chloro-2-pyridine-carboxylic acid (200 mg, 1.26 mmol), HATU (720 mg, 1.89 mmol), ( S )-1-(trimethylsilyl)propane in anhydrous DMF (3 mL) A solution of -2-ammonium chloride ( C6 ; 212 mg, 1.26 mmol) and N -ethyldiisopropylamine (441 μL, 2.52 mmol) was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was dissolved in dichloromethane (25 mL). The organic layer was washed with brine (3 x 10 mL), dried over sodium sulfate, and concentrated. Purification by flash column chromatography (using hexane and ethyl acetate-ethanol (3:1)) gave the title compound (242 mg, 67%) as a white solid: 1 H NMR (500 MHz, CDCl 3 ) δ 8.52 (d, J = 2.3 Hz, 1H), 8.47 (d, J = 2.3 Hz, 1H), 7.41 (d, J = 6.7 Hz, 1H), 4.30 (tt, J = 8.2, 6.6 Hz, 1H), 1.31 (d, J = 6.5 Hz, 3H), 1.04 (dd, J = 14.5, 6.7 Hz, 1H), 0.89 (dd, J = 14.5, 8.0 Hz, 1H), 0.07 (s, 9H); 13 C NMR (126 MHz, CDCl 3 ) δ 160.63, 148.28, 145.44, 143.42, 140.47, 43.61, 25.84, 23.99, -0.93. ESIMS m/z 270 ([MH] - ). Preparation of (S) -3- ethyl-2-chloride (C3): Synthetic Intermediates Example 4 Preparation of (3-ethyl-2-ylidene) -2-methylpropane-2-sulfinyl amines (C1) is - Step 1 - (R, Z) - N
向配備磁性攪拌棒的50-mL單頸圓底燒瓶中依次裝入(R )-三級丁 烷亞磺醯胺(1 g,8.3 mmol)、四氫呋喃(THF;10 mL)、3-乙基戊-2-酮(1.13 g,9.90 mmol)、和甲醇鈦(IV)(Ti(OEt)4 ;(5.18 mL,24.8 mmol))。該混合物在70°C下攪拌過夜。將該反應混合物冷卻至室溫並用水(10 mL)淬滅。將乙酸乙酯(25 mL)添加到混合物中,並且將獲得的固體物質經矽藻土過濾。分離各相並且將該水相用乙酸乙酯(2 x 25 mL)萃取。將合併的有機相用鹽水(25 mL)洗滌並且經硫酸鈉乾燥。將溶劑在真空中濃縮以得到油狀物,該油狀物無需進一步純化即可進行步驟2:1 H NMR (500 MHz, CDCl3 ) δ 2.28 (s, 3H), 2.25 - 2.15 (m, 1H), 1.68 - 1.47 (m, 4H), 1.24 (s, 9H), 0.88 (td,J = 7.5, 1.4 Hz, 6H);ESIMSm/z 218 ([M+H]+ )。步驟 2 - (R )-N -((S )-3- 乙基戊 -2- 基 )-2- 甲基丙烷 -2- 亞磺醯胺 (C2) 的製備 To a 50-mL single-neck round bottom flask equipped with a magnetic stirring bar was successively charged with (R) - butane three sulfinyl amine (1 g, 8.3 mmol), tetrahydrofuran (THF; 10 mL), 3- ethyl Pentan-2-one (1.13 g, 9.90 mmol), and titanium (IV) methoxide (Ti(OEt) 4 ; (5.18 mL, 24.8 mmol)). The mixture was stirred at 70°C overnight. The reaction mixture was cooled to room temperature and quenched with water (10 mL). Ethyl acetate (25 mL) was added to the mixture, and the obtained solid matter was filtered through Celite. The phases were separated and the aqueous phase was extracted with ethyl acetate (2 x 25 mL). The combined organic phase was washed with brine (25 mL) and dried over sodium sulfate. The solvent was concentrated in vacuo to obtain an oil, which can be carried out to Step 2: 1 H NMR (500 MHz, CDCl 3 ) δ 2.28 (s, 3H), 2.25-2.15 (m, 1H) without further purification ), 1.68-1.47 (m, 4H), 1.24 (s, 9H), 0.88 (td, J = 7.5, 1.4 Hz, 6H); ESIMS m/z 218 ([M+H] + ). Step 2- Preparation of (R ) -N -(( S )-3 -ethylpent -2- yl )-2 -methylpropane -2 -sulfinamide (C2)
向冷卻至-45°C的無水THF(10 mL)中的(R ,Z )-N -(3-乙基戊-2-基亞基)-2-甲基丙烷-2-亞磺醯胺(C1 ,由步驟1獲得的;1.79 g,8.25 mmol)溶液中滴加三二級丁基硼氫化鋰(THF中1莫耳(M);29 mL,29 mmol)。去除冷卻浴,並且將反應混合物在室溫下攪拌3小時。將反應混合物冷卻至0°C並且藉由滴加甲醇淬滅直到發泡停止。劇烈攪拌該混合物,並且將鹽水(10 mL)添加到混合物中,給出白色懸浮液。經矽藻土過濾該混合物,並且用乙酸乙酯(50 mL)洗滌濾餅。收集濾液,並用等體積的鹽水洗滌。用乙酸乙酯(2 x 25 mL)萃取該水層。將有機相合併,經硫酸鈉乾燥,並且濃縮。獲得的油狀物無需純化即可進行下一步。步驟 3 - (S )-3- 乙基戊 -2- 氯化銨 (C3) 的製備 To (R , Z ) -N -(3-ethylpent-2-ylidene)-2-methylpropane-2-sulfinamide in dry THF (10 mL) cooled to -45°C ( C1 , obtained from step 1; 1.79 g, 8.25 mmol) Lithium tertiary butyl borohydride (1 mol (M) in THF; 29 mL, 29 mmol) was added dropwise to the solution. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was cooled to 0°C and quenched by the dropwise addition of methanol until foaming ceased. The mixture was stirred vigorously, and brine (10 mL) was added to the mixture to give a white suspension. The mixture was filtered through Celite, and the filter cake was washed with ethyl acetate (50 mL). The filtrate was collected and washed with an equal volume of brine. The aqueous layer was extracted with ethyl acetate (2 x 25 mL). The organic phases were combined, dried over sodium sulfate, and concentrated. The oil obtained can be used for the next step without purification. Step 3- Preparation of (S )-3 -ethylpentan -2- ammonium chloride (C3)
將來自步驟2的油產物溶解於甲醇(5 mL)中並用二㗁𠮿中的4 N HCl(5 mL)處理。將反應混合物在室溫下攪拌2小時。在真空下濃縮溶劑並將殘餘物在真空下乾燥。將分離的物質用乙醚研磨以獲得白色固體,過濾白色固體,用乙醚洗滌,並且乾燥。分離出呈白色固體的標題化合物(526 mg,42%):1 H NMR (500 MHz, CDCl3 ) δ 8.33 (s, 3H), 3.39 (h,J = 6.1 Hz, 1H), 1.66 - 1.42 (m, 4H), 1.35 (d,J = 6.7 Hz, 3H), 1.33 - 1.28 (m, 1H), 0.94 (td,J = 7.4, 3.1 Hz, 6H);13 C NMR (126 MHz, DMSO-d 6 ) δ 48.63, 43.97, 21.89, 20.65, 14.89, 11.85, 11.75。實例 5 : (S )-1-( 三甲基矽基 ) 丙 -2- 氯化銨 (C6) 的製備 步驟 1 - (S )-N - 亞乙基 -2- 甲基丙烷 -2- 亞磺醯胺 (C4) 的製備 Dissolve the oil product from step 2 in methanol (5 mL) and treat with 4 N HCl (5 mL) in dioxins. The reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated under vacuum and the residue was dried under vacuum. The separated material was triturated with ether to obtain a white solid, the white solid was filtered, washed with ether, and dried. The title compound (526 mg, 42%) was isolated as a white solid: 1 H NMR (500 MHz, CDCl 3 ) δ 8.33 (s, 3H), 3.39 (h, J = 6.1 Hz, 1H), 1.66-1.42 ( m, 4H), 1.35 (d, J = 6.7 Hz, 3H), 1.33-1.28 (m, 1H), 0.94 (td, J = 7.4, 3.1 Hz, 6H); 13 C NMR (126 MHz, DMSO- d 6 ) δ 48.63, 43.97, 21.89, 20.65, 14.89, 11.85, 11.75. Example 5 : Preparation of ( S )-1-( trimethylsilyl ) propane -2- ammonium chloride (C6) Step 1- Preparation of (S ) -N - ethylene- 2 -methylpropane -2 -sulfinamide (C4)
向配備磁性攪拌棒的乾燥圓底燒瓶中添加乙醛(2.80 mL,50 mmol)、(S )-三級丁烷亞磺醯胺(2 g,17 mmol)和THF(5 mL)。用橡膠隔片密封該燒瓶。用三(2,2,2-三氟乙基)硼酸(3.55 mL,16.5 mmol)滴加處理反應混合物,並且將該溶液在室溫下攪拌過夜。用乙酸乙酯稀釋該反應混合物,並且用飽和碳酸氫鈉水溶液和水洗滌該溶液。然後將有機相經硫酸鈉乾燥,過濾,並濃縮。分離出呈棕色液體的標題化合物,其無需任何純化即可用於下一步驟(2.05 g,84%):1 H NMR (400 MHz, CDCl3 ) δ 8.09 (q,J = 5.1 Hz, 1H), 2.24 (d,J = 5.2 Hz, 3H), 1.20 (s, 9H);ESIMSm/z 148 ([M+H]+ )。步驟 2 - (S )-2- 甲基 -N -((S )-1-( 三甲基矽基 ) 丙 -2- 基 ) 丙烷 -2- 亞磺醯胺 (C5) 的製備 To a dry round bottom flask equipped with a magnetic stir bar, acetaldehyde (2.80 mL, 50 mmol), ( S )-tertiary butanesulfinamide (2 g, 17 mmol) and THF (5 mL) were added. The flask was sealed with a rubber septum. The reaction mixture was treated dropwise with tris(2,2,2-trifluoroethyl)boronic acid (3.55 mL, 16.5 mmol), and the solution was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the solution was washed with a saturated aqueous sodium hydrogen carbonate solution and water. The organic phase was then dried over sodium sulfate, filtered, and concentrated. The title compound is isolated as a brown liquid, which can be used in the next step without any purification (2.05 g, 84%): 1 H NMR (400 MHz, CDCl 3 ) δ 8.09 (q, J = 5.1 Hz, 1H), 2.24 (d, J = 5.2 Hz, 3H), 1.20 (s, 9H); ESIMS m/z 148 ([M+H] + ). Step 2- Preparation of (S )-2- Methyl - N -(( S )-1-( Trimethylsilyl ) prop -2- yl ) propane -2 -sulfinamide (C5)
在-45°C下,向無水二氯甲烷(10 mL)中的(S )-N -亞乙基-2-甲基丙烷-2-亞磺醯胺(從步驟1獲得;2.05 g,13.9 mmol)的溶液中滴加(三甲基矽基)甲基氯化鎂(乙醚中的1 M溶液;42 mL,42 mmol)。允許反應混合物升溫至室溫並攪拌過夜。將反應混合物冷卻至0°C並且用飽和氯化銨水溶液緩慢淬滅。用乙酸乙酯(2 x 50 mL)萃取該混合物。將合併的有機提取物經硫酸鈉乾燥,過濾並在真空中濃縮。分離出呈淡黃色油狀物的標題化合物,其無需任何純化即可用於下一步驟:1 H NMR (400 MHz, CDCl3 ) δ 3.69 - 3.50 (m, 1H), 3.02 (d,J = 3.6 Hz, 1H), 1.23 - 1.14 (m, 12H), 1.01 (dd,J = 14.2, 4.6 Hz, 1H), 0.86 (dd,J = 14.3, 9.7 Hz, 1H), 0.06 (s, 9H);ESIMSm/z 236 ([M+H]+ )。步驟 3 - (S )-1-( 三矽基 ) 丙 -2- 氯化銨 (C6) 的製備 Add ( S ) -N -ethylene-2-methylpropane-2-sulfinamide (obtained from step 1; 2.05 g, 13.9 mmol) was added dropwise (trimethylsilyl) methyl magnesium chloride (1 M solution in ether; 42 mL, 42 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0°C and slowly quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated as a pale yellow oil, which can be used in the next step without any purification: 1 H NMR (400 MHz, CDCl 3 ) δ 3.69-3.50 (m, 1H), 3.02 (d, J = 3.6 Hz, 1H), 1.23-1.14 (m, 12H), 1.01 (dd, J = 14.2, 4.6 Hz, 1H), 0.86 (dd, J = 14.3, 9.7 Hz, 1H), 0.06 (s, 9H); ESIMS m/z 236 ([M+H] + ). Step 3- Preparation of (S )-1-( Trisilyl ) propan -2- ammonium chloride (C6)
將獲得自步驟2的油狀物溶解於甲醇(5 mL)中並用二㗁𠮿中的4 N HCl(10 mL)處理。將反應混合物在室溫下攪拌4小時。在真空下濃縮溶劑並將殘餘物在真空下乾燥。將分離的物質用乙醚研磨以獲得白色固體,過濾白色固體,用乙醚洗滌,並且乾燥。分離出呈白色固體的標題化合物(1.0 g,43%):1 H NMR (500 MHz, CDCl3 ) δ 8.25 (s, 3H), 3.60 - 3.35 (m, 1H), 1.43 (d,J = 6.5 Hz, 3H), 1.24 (dd,J = 14.0, 3.1 Hz, 1H), 1.07 (dd,J = 13.9, 12.2 Hz, 1H), 0.07 (s, 9H)。13 C NMR (126 MHz, CDCl3 ) δ 47.11, 24.18, 21.00, -1.05;ESIMSm/z 168 ([M+H]+ )。The oil obtained from step 2 was dissolved in methanol (5 mL) and treated with 4 N HCl (10 mL) in dichloromethane. The reaction mixture was stirred at room temperature for 4 hours. The solvent was concentrated under vacuum and the residue was dried under vacuum. The separated material was triturated with ether to obtain a white solid, the white solid was filtered, washed with ether, and dried. The title compound (1.0 g, 43%) was isolated as a white solid: 1 H NMR (500 MHz, CDCl 3 ) δ 8.25 (s, 3H), 3.60-3.35 (m, 1H), 1.43 (d, J = 6.5 Hz, 3H), 1.24 (dd, J = 14.0, 3.1 Hz, 1H), 1.07 (dd, J = 13.9, 12.2 Hz, 1H), 0.07 (s, 9H). 13 C NMR (126 MHz, CDCl 3 ) δ 47.11, 24.18, 21.00, -1.05; ESIMS m/z 168 ([M+H] + ).
可根據上述實例和報導的條件,製造具有根據式一
的結構且在表1中列出的下列分子。
南方根結線蟲(RKN)係最具破壞性和經濟上重要的植物寄生線蟲。這種線蟲以植物根、塊莖、球莖和根莖為食,導致數量和品質上的產量損失。線蟲在根上引起特徵性的結,稱為癭。處理植物線蟲的最有效方式是藉由化學殺線蟲劑的使用,該化學殺線蟲劑基於揮發性被分為熏劑和非熏劑。熏劑化合物通常是鹵代烴和異硫氰酸酯的先質,該異硫氰酸酯通常提供土壤有害生物和病害病原的廣譜的、不加選擇的控制。非熏劑化合物(主要是有機磷酸酯類或胺基甲酸酯類)係乙醯膽鹼抑制劑並且提供目標生物體的窄譜。然而,大多數殺線蟲劑由於健康和環境問題已經被淘汰,這已導致了世界範圍內線蟲問題的再出現和對安全和有效的化學品的搜索以管理該等有害生物。 測試ARoot-knot nematode (RKN) is the most destructive and economically important plant parasitic nematode. This nematode feeds on plant roots, tubers, bulbs and rhizomes, resulting in yield loss in quantity and quality. Nematodes cause characteristic knots on the roots, called galls. The most effective way to treat plant nematodes is through the use of chemical nematicides, which are classified into fumigants and non-fumigants based on volatility. Fumigant compounds are usually precursors of halogenated hydrocarbons and isothiocyanates, which generally provide broad-spectrum, indiscriminate control of soil pests and disease pathogens. Non-fumigant compounds (mainly organophosphates or carbamates) are acetylcholine inhibitors and provide a narrow spectrum of target organisms. However, most nematicides have been eliminated due to health and environmental issues, which has led to the reappearance of nematode problems worldwide and the search for safe and effective chemicals to manage these pests. Test A
將在3-英吋的盆的土壤中生長的6日齡之黃瓜植物(黃瓜(Cucumis sativus ))用5 mL百萬分之100、50、和25(ppm)在水中的5%丙酮中溶解的測試化合物的處理。每個實驗化合物或標準重複三次。之後用RKN的1000隻二齡幼蟲接種植物。在評估根損害(癭)(基於0至10的標度,其中0 = 無癭(100%控制)和10 = 最大的癭(無控制))之前,將接種植物在溫室中養植14天。 A 6-day-old cucumber plant (Cucumis sativus ) grown in the soil of a 3-inch pot was dissolved in 5 mL of 100, 50, and 25 parts per million (ppm) in 5% acetone in water The treatment of the test compound. Each test compound or standard was repeated three times. The plants were then inoculated with 1000 second-instar larvae of RKN. Before evaluating root damage (gall) (based on a scale of 0 to 10, where 0 = no gall (100% control) and 10 = maximum gall (no control)), the inoculated plants are grown in the greenhouse for 14 days.
控制百分比(%)= (10 - GI) x 10, 其中GI = 癭指數(以0至10的標度的癭的量)。Control percentage (%) = (10-GI) x 10, Where GI = gall index (the amount of gall on a scale of 0 to 10).
測試A的結果參見表A。在結果報告中,使用「RKN 評級表 」。 測試BSee Table A for the results of Test A. In the result report, use the " RKN Rating Form ". Test B
將六(6)mg的每個實驗或標準化合物溶解於60 mL溶劑(在水中的10%丙酮)中以配製成100 ppm濃度的溶液。標記第0周至第4週的盆栽土壤(每個三(3)個重複)用五(5)mL的100 ppm化合物測試溶液浸透表面。Six (6) mg of each experimental or standard compound was dissolved in 60 mL of solvent (10% acetone in water) to make a 100 ppm concentration solution. Mark potting soil from week 0 to week 4 (three (3) repetitions each) soak the surface with five (5) mL of 100 ppm compound test solution.
第0週的處理:將處理施用給上述土壤(5 mL/盆),並且將六日齡之黃瓜幼苗移植進土壤中並立即接種1000隻二齡RKN幼蟲。Treatment at week 0: Apply the treatment to the above soil (5 mL/pot), and transplant six-day-old cucumber seedlings into the soil and immediately inoculate 1000 second-instar RKN larvae.
第1週的處理:在施用後七(7)天,將六日齡之黃瓜幼苗移植進標記第1週的盆中並且立即接種1000隻二齡RKN幼蟲(三個重複)。Treatment for the first week: Seven (7) days after the application, the six-day-old cucumber seedlings were transplanted into the pot marked the first week and immediately inoculated with 1000 second-instar RKN larvae (three replicates).
第2週的處理:在施用後十四(14)天,將六日齡之黃瓜幼苗移植進標記第2週的盆中並且立即接種1000隻二齡RKN幼蟲(三個重複)。Treatment for the second week: Fourteen (14) days after the application, six-day-old cucumber seedlings were transplanted into pots marked the second week and immediately inoculated with 1000 second-instar RKN larvae (three replicates).
第4週之處理:在施用後二十八(28)天,將六日齡之黃瓜幼苗移植進標記第4週的盆中並且立即接種1000隻二齡RKN幼蟲(三個重複)。Treatment for the 4th week: Twenty-eight (28) days after application, transplant 6-day-old cucumber seedlings into pots marked 4th week and immediately inoculate 1000 second-instar RKN larvae (three replicates).
在評估根損害(癭)(基於0至10的標度,其中0 = 無癭(100%控制)和10 = 最大的癭(無控制))之前,將接種植物在溫室中養植14天。Before evaluating root damage (gall) (based on a scale of 0 to 10, where 0 = no gall (100% control) and 10 = maximum gall (no control)), the inoculated plants are grown in the greenhouse for 14 days.
控制百分比(%)= (10 - GI) x 10, 其中GI = 癭指數(癭的量)Control percentage (%) = (10-GI) x 10, Where GI = gall index (amount of gall)
測試B的結果參見表B。在結果報告中,使用「RKN 評級表 」。See Table B for the results of Test B. In the result report, use the " RKN Rating Form ".
表格部分
可以將式一的分子配製成農業上可接受的酸加成鹽。作為非限制性實例,胺官能基可與鹽酸、氫溴酸、硫酸、磷酸、乙酸、苯甲酸、檸檬酸、丙二酸、水楊酸、蘋果酸、反丁烯二酸、乙二酸、丁二酸、酒石酸、乳酸、葡萄糖酸、抗壞血酸、順丁烯二酸、天冬胺酸、苯磺酸、甲磺酸、乙磺酸、羥基甲磺酸、和羥基乙磺酸形成鹽。另外,作為非限制性實例,酸官能基可形成鹽,該鹽包括由鹼金屬或鹼土金屬衍生的鹽和由胺和胺衍生的鹽。較佳的陽離子的實例包括鈉、鉀、和鎂。The molecules of Formula One can be formulated as agriculturally acceptable acid addition salts. As non-limiting examples, amine functional groups can be combined with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, benzoic acid, citric acid, malonic acid, salicylic acid, malic acid, fumaric acid, oxalic acid, Succinic acid, tartaric acid, lactic acid, gluconic acid, ascorbic acid, maleic acid, aspartic acid, benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, hydroxymethanesulfonic acid, and hydroxyethanesulfonic acid form salts. In addition, as a non-limiting example, acid functional groups may form salts, which include salts derived from alkali metals or alkaline earth metals and salts derived from amines and amines. Examples of preferred cations include sodium, potassium, and magnesium.
可以將式一的分子配製成鹽衍生物。作為非限制性實例,可藉由使游離鹼與足以產生鹽的量的所希望的酸接觸來製備鹽衍生物。可藉由將該鹽用合適的稀鹼水溶液(如稀氫氧化鈉、碳酸鉀、胺、和碳酸氫鈉水溶液)處理來再生游離鹼。例如,在許多情況下,殺有害生物劑(諸如2,4-D)藉由將其轉化成其二甲胺鹽而更可溶於水。The molecule of Formula One can be formulated as a salt derivative. As a non-limiting example, a salt derivative can be prepared by contacting the free base with the desired acid in an amount sufficient to produce the salt. The free base can be regenerated by treating the salt with a suitable dilute aqueous alkali solution (such as dilute sodium hydroxide, potassium carbonate, amine, and sodium bicarbonate aqueous solutions). For example, in many cases, pesticides such as 2,4-D are more soluble in water by converting them into their dimethylamine salt.
可以將具有式一的分子與溶劑一起配製成穩定複合物,使得該複合物在去除非複合溶劑之後保持完整。該等複合物常稱為「溶劑化物」。然而,特別希望的是使用水作為溶劑以形成穩定的水合物。The molecule with formula one can be formulated with a solvent to form a stable complex, so that the complex remains intact after removing the non-complexing solvent. These complexes are often referred to as "solvates". However, it is particularly desirable to use water as a solvent to form stable hydrates.
可以將具有式一的分子製成酯衍生物。然後可以與應用本文件中所揭露的分子相同的方式應用該等酯衍生物。Molecules with Formula One can be made into ester derivatives. These ester derivatives can then be applied in the same way as the molecules disclosed in this document.
可以將式一的分子製成為多種同質異晶物。同質異晶現象在農用化學品開發中是重要的,因為相同分子的不同晶體同質異晶物或結構可具有大大不同的物理特性和生物性能。The molecules of Formula One can be made into a variety of isomorphs. The isomorphism is important in the development of agrochemicals, because different crystal isomorphs or structures of the same molecule can have greatly different physical properties and biological properties.
可以用不同的同位素製造具有式一的分子。特別重要的是具有2 H(也稱為氘)代替1 H的分子。Different isotopes can be used to make molecules with formula one. Of particular importance are molecules with 2 H (also called deuterium) instead of 1 H.
可以用不同放射性核素製造式一的分子。特別重要的是具有14 C的分子。立體異構物 Different radionuclides can be used to make molecules of Formula One. Particularly important are molecules with 14 C. Stereoisomers
具有式一的分子可作為一種或多種立體異構物而存在。因此,某些分子可以外消旋混合物的形式而產生。本領域技術者將理解,一種立體異構物可以比其他立體異構物更具活性。單獨的立體異構物可以藉由已知的選擇性合成程序、藉由使用拆分的起始材料的常規合成程序、或藉由常規拆分程序獲得。本文件中所揭露的某些分子可作為兩種或更多種異構物而存在。不同異構物包括幾何異構物、非鏡像異構物、和鏡像異構物。因此,本文件中揭露的分子包括幾何異構物、外消旋混合物、單獨的立體異構物、和旋光混合物。為清楚起見,本揭露中揭露的結構可以僅以一種幾何形式繪製,但旨在表示該分子的所有幾何形式。組合 Molecules with Formula One may exist as one or more stereoisomers. Therefore, certain molecules can be produced as racemic mixtures. Those skilled in the art will understand that one stereoisomer can be more active than other stereoisomers. Individual stereoisomers can be obtained by known selective synthesis procedures, by conventional synthesis procedures using resolved starting materials, or by conventional resolution procedures. Certain molecules disclosed in this document can exist as two or more isomers. Different isomers include geometric isomers, diastereomers, and enantiomers. Therefore, the molecules disclosed in this document include geometric isomers, racemic mixtures, individual stereoisomers, and optically active mixtures. For clarity, the structure disclosed in this disclosure may be drawn in only one geometric form, but it is intended to represent all geometric forms of the molecule. combination
在另一個實施方式中,具有式一的分子可與一種或多種化合物組合使用(如以組分混合物形式、或同時或依次應用),該一種或多種化合物各自具有與具有式一的分子的作用模式(「MoA」)相同、類似、或不同的作用模式。作用模式包括,例如以下:乙醯膽鹼酯酶(AChE)抑制劑;GABA閘控氯通道拮抗劑;鈉通道調節器;菸鹼乙醯膽鹼(nAChR)促效劑;菸鹼乙醯膽鹼受體(nAChR)變構活化劑;氯通道活化劑;保幼激素模擬物;混雜非特異性(多位點)抑制劑;選擇性同翅昆蟲飼養阻斷劑;蟎蟲生長抑制劑;昆蟲中腸膜的微生物破壞劑;粒線體ATP合成酶抑制劑;藉由破壞質子梯度而進行氧化磷酸化的解偶合劑;菸鹼乙醯膽鹼受體(nAChR)通道阻斷劑;0型幾丁質生物合成抑制劑;1型幾丁質生物合成抑制劑;蛻皮干擾劑,雙翅目;蛻皮激素受體促效劑;真蛸胺受體促效劑;粒線體複合體III電子傳遞抑制劑;粒線體複合體I電子傳遞抑制劑;電壓依賴型鈉通道阻斷劑;乙醯CoA羧化酶抑制劑;粒線體複合體IV電子傳遞抑制劑;粒線體複合體II電子傳遞抑制劑;利阿諾定受體調節劑;聲音反應型器官TRPV通道調節劑;聲音反應型器官調節劑 - 未定義的靶位點;GABA閘控氯變構調節劑;桿狀病毒;菸鹼型乙醯膽鹼受體(nAChR)變構調節劑 - 位點II;未知或不確定MoA之化合物;未知或不確定MoA的細菌試劑(非-Bt);包括合成的,提取物,和具有未知或不確定MoA的未精製的油狀物的植物精華;未知或不確定MoA的真菌試劑;和非特異性機械干擾物。In another embodiment, the molecule having Formula One can be used in combination with one or more compounds (eg, in the form of a mixture of components, or applied simultaneously or sequentially), and each of the one or more compounds has an effect with the molecule having Formula One. Mode ("MoA") the same, similar, or different mode of action. Modes of action include, for example, the following: acetylcholinesterase (AChE) inhibitors; GABA gated chloride channel antagonists; sodium channel regulators; nicotinic acetylcholine (nAChR) agonists; nicotinic acetylcholine Alkaline receptor (nAChR) allosteric activator; Chlorine channel activator; Juvenile hormone mimics; Mixed non-specific (multi-site) inhibitors; Selective homopteran feeding blockers; Mite growth inhibitors; Insects Microbial disruptors of the midgut membrane; mitochondrial ATP synthase inhibitors; decoupling agents for oxidative phosphorylation by disrupting the proton gradient; nicotinic acetylcholine receptor (nAChR) channel blockers; type 0 Chitin Biosynthesis Inhibitor; Type 1 Chitin Biosynthesis Inhibitor; Moulting Interfering Agent, Diptera; Ecdysone Receptor Agonist; Ectoamine Receptor Agonist; Mitochondrial Complex III Electron Transport Inhibitor; Mitochondrial complex I electron transport inhibitor; Voltage-dependent sodium channel blocker; Acetyl CoA carboxylase inhibitor; Mitochondrial complex IV electron transport inhibitor; Mitochondrial complex II electron Delivery inhibitors; Lianodine receptor modulators; Sound-responsive organ TRPV channel modulators; Sound-responsive organ modulators-undefined target sites; GABA gated chlorine allosteric modulators; Baculovirus; Smoke Alkaline Acetylcholine Receptor (nAChR) Allosteric Modulator-Site II; Unknown or uncertain MoA compound; Unknown or uncertain MoA bacterial reagent (non-Bt); including synthetic, extract, and Unrefined oily plant extracts with unknown or uncertain MoA; fungal agents with unknown or uncertain MoA; and non-specific mechanical interferences.
在另一個實施方式中,具有式一的分子可與具有殺蜱蟎亞綱動物、殺藻、殺鳥、殺細菌、殺真菌、除草、殺昆蟲、殺軟體動物、殺線蟲、殺齧齒動物、和/或殺病毒特性的一種或多種化合物組合使用(如以組分混合物形式、或同時或依次應用)。In another embodiment, a molecule having Formula One can be combined with acaridicidal, algaecidal, avian, bactericidal, fungicidal, weedicidal, insecticidal, mollusc, nematicidal, rodent, And/or one or more compounds with antiviral properties are used in combination (for example, in the form of a mixture of components, or simultaneously or sequentially).
在另一個實施方式中,具有式一的分子可與作為拒食劑、驅鳥劑、化學不育劑、除草劑安全劑、昆蟲引誘劑、驅昆蟲劑、驅哺乳動物劑、交配干擾劑、植物活化劑、植物生長調節劑、和/或增效劑的一種或多種化合物組合使用(如以組分混合物形式、或同時或依次應用)。In another embodiment, the molecule with Formula One can be used as antifeedant, bird repellent, chemical sterilization agent, herbicide safener, insect attractant, insect repellent, mammal repellent, mating disruptor, plant One or more compounds of activator, plant growth regulator, and/or synergist are used in combination (for example, in the form of a mixture of components, or simultaneously or sequentially).
在另一個實施方式中,以上可能的組合可以以多種重量比使用。例如,兩種組分的混合物,即具有式一的分子與另一種化合物的重量比,可以為約100 : 1至約1 : 100;在另一個實例中,重量比可以為約50 : 1至約1 : 50;在另一個實例中,重量比可以為約20 : 1至約1 : 20;在另一個實例中,重量比可以為約10 : 1至約1 : 10;在另一個實例中,重量比可以為約5 : 1至約1 : 5;在另一個實例中,重量比可以為約3 : 1至約1 : 3;並且在最終的實例中,重量比可以為約1 : 1。然而,較佳的是,小於約10 : 1至約1 : 10之重量比係較佳的。有時還較佳的使用包含一種或多種具有式一的分子和來自上述可能的組合的一種或多種其他化合物的三組分或四組分混合物。配製物 In another embodiment, the above possible combinations can be used in various weight ratios. For example, a mixture of two components, that is, the weight ratio of a molecule having Formula One to another compound, can be from about 100:1 to about 1:100; in another example, the weight ratio can be from about 50:1 to about 50:1. About 1:50; in another example, the weight ratio may be about 20:1 to about 1:20; in another example, the weight ratio may be about 10:1 to about 1:10; in another example , The weight ratio may be about 5:1 to about 1:5; in another example, the weight ratio may be about 3:1 to about 1:3; and in the final example, the weight ratio may be about 1:1 . However, preferably, a weight ratio of less than about 10:1 to about 1:10 is preferred. Sometimes it is also preferable to use a three-component or four-component mixture comprising one or more molecules with formula one and one or more other compounds from the above possible combinations. Formulation
本文揭露之化合物一般將用作組成物(即配製物)中的寄生線蟲控制活性成分,其中至少一種選自由表面活性劑、固體稀釋劑、和液體稀釋劑組成之群組的額外組分,用作載體。選擇該配製物或組成物成分,以與活性成分的物理特性、施用模式和環境因素諸如土壤類型、水分和溫度一致。The compound disclosed herein will generally be used as a parasitic nematode control active ingredient in a composition (ie, a formulation), wherein at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents is used As a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, moisture, and temperature.
有用的配製物包括液體和固體組成物二者。液體組成物包括溶液(包括可乳化的濃縮物)、懸浮液、乳液(包括微乳液和/或懸乳液)等,它們可以視需要被增稠成凝膠。水性液體組成物的一般類型為可溶性濃縮物、懸浮液濃縮物、膠囊懸浮液、濃縮乳液、微乳液和懸乳液。非水性液體組成物的一般類型為可乳化的濃縮物、可微乳化的濃縮物、可分散的濃縮物和油分散體。Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions), etc., and they can be thickened into gels as needed. The general types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions and suspoemulsions. The general types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.
固體組成物的一般類型為粉劑、粉末、顆粒劑、小丸劑、粒料、錠劑、片劑、填充膜(包括種子包衣)等,它們可以是水可分散的(「可潤濕的」)或水溶性的。由成膜溶液或可流動的懸浮液形成的膜和包衣特別可用於種子處理。活性成分可以被(微)封裝,並且進一步形成懸浮液或固體配製物;可替代地,活性成分的整個配製物可以被封裝(或「包覆」)。包封可以控制或延遲活性成分的釋放。可乳化的顆粒劑結合了可乳化的濃縮物配製物和乾顆粒配製物兩者的優點。高強度組成物主要用作進一步配製物的中間體。The general types of solid compositions are powders, powders, granules, pellets, granules, lozenges, tablets, filled films (including seed coatings), etc. They can be water-dispersible ("wettable" ) Or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. The active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively, the entire formulation of the active ingredient can be encapsulated (or "coated"). Encapsulation can control or delay the release of active ingredients. Emulsifiable granules combine the advantages of both emulsifiable concentrate formulations and dry granular formulations. High-strength compositions are mainly used as intermediates for further formulations.
可噴霧的配製物通常在噴霧之前分散在適宜的介質中。將此類液體配製物和固體配製物配製成易於在噴霧介質(通常為水)中稀釋的配製物。噴霧體積的範圍可以為每公頃從約一升至幾千升,但更典型為在每公頃從約十至幾百升的範圍內。可噴霧的配製物可在槽中與水或另一種合適的介質混合,用於藉由空氣或地面施用來進行葉處理,或用於施用到植物的生長介質中。液體和無水配製物可以直接計量添加至滴灌系統中,或在種植期間計量添加至壟溝中。液體和固體配製物可在種植之前作為種子處理劑施用到作物和其他期望的植被的種子上,以便藉由內吸吸收來保護發育中的根和其他地面下的植物部分和/或葉。Sprayable formulations are usually dispersed in a suitable medium before spraying. Such liquid formulations and solid formulations are formulated into formulations that are easy to dilute in a spray medium (usually water). The spray volume can range from about one liter to several thousand liters per hectare, but is more typically in the range from about ten to several hundred liters per hectare. The sprayable formulation can be mixed with water or another suitable medium in a tank, for foliar treatment by air or ground application, or for application to the growing medium of plants. Liquid and anhydrous formulations can be metered directly into the drip irrigation system, or metered into the furrow during planting. Liquid and solid formulations can be applied as seed treatments to the seeds of crops and other desired vegetation prior to planting in order to protect the developing roots and other below-ground plant parts and/or leaves by systemic absorption.
配製物通常將含有總計達100重量百分比的在以下近似範圍內的有效量之活性成分、稀釋劑和表面活性劑。The formulation will generally contain up to 100 weight percent of active ingredients, diluents, and surfactants in effective amounts in the approximate ranges below.
固體稀釋劑包括,例如,黏土諸如膨潤土、蒙脫土、凹凸棒石和高嶺土、石膏、纖維素、二氧化鈦、氧化鋅、澱粉、糊精、糖(例如,乳糖、蔗糖)、二氧化矽、滑石、雲母、矽藻土、脲、碳酸鈣、碳酸鈉和碳酸氫鈉、以及硫酸鈉。典型的固體稀釋劑在Watkins等人的Handbook of Insecticide Dust Diluents and Carriers [殺昆蟲劑粉劑稀釋劑和載體手冊], 第2版, Dorland Books, 考德威爾, 新澤西州中有所描述。Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugar (for example, lactose, sucrose), silica, talc, Mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al. Handbook of Insecticide Dust Diluents and Carriers , 2nd edition, Dorland Books, Caldwell, New Jersey.
液體稀釋劑包括,例如水、N,N -二甲基烷醯胺(例如,N ,N- 二甲基甲醯胺)、檸檬烯、二甲基亞碸、N- 烷基吡咯啶酮(例如,N- 甲基吡咯啶酮)、乙二醇、三甘醇、丙二醇、二丙二醇、聚丙二醇、碳酸丙烯酯、碳酸丁烯酯、石蠟(例如白礦物油、正鏈烷烴、異鏈烷烴)、烷基苯、烷基萘、甘油、三乙酸甘油酯、山梨糖醇、三乙酸甘油酯、芳烴、脫芳構化脂族化合物、烷基苯、烷基萘、酮,諸如環己酮、2-庚酮、異佛爾酮、和4-羥基-4-甲基-2-戊酮,乙酸酯,諸如乙酸異戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酯、乙酸十三烷基酯、和乙酸異莰酯,其他酯,諸如烷基化乳酸酯、二元酯、和γ-丁內酯,以及可以是直鏈、支鏈、飽和或不飽和的醇,諸如甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、正己醇、2-乙基己醇、正辛醇、癸醇、異癸醇、異十八烷醇、鯨蠟醇、月桂醇、十三烷醇、油醇、環己醇、四氫糠醇、雙丙酮醇、和苄醇。液體稀釋劑還包括飽和的和不飽和的脂肪酸(典型地為C6 -C22 )的甘油酯,諸如植物種子和果實油(例如,橄欖油、蓖麻油、亞麻籽油、芝麻油、玉米油(玉蜀黍油)、花生油、葵花籽油、葡萄籽油、紅花油、棉籽油、大豆油、油菜籽油、椰子油和棕櫚仁油),動物源脂肪(例如,牛脂、豬脂、豬油、魚肝油、魚油),以及它們之混合物。液體稀釋劑還包括烷基化(例如甲基化、乙基化、丁基化)脂肪酸,其中脂肪酸可以藉由來自植物和動物來源的甘油酯的水解獲得,並且可藉由蒸餾純化。典型的液體稀釋劑在Marsden,Solvents Guide [溶劑指南], 第2版, Interscience, 紐約, 1950中進行描述。Liquid diluents include, for example, water, N,N -dimethylalkaneamide (for example, N , N -dimethylformamide), limonene, dimethylsulfene, and N- alkylpyrrolidone (for example , N -methylpyrrolidone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (such as white mineral oil, normal paraffin, isoparaffin) , Alkylbenzene, alkylnaphthalene, glycerol, triacetin, sorbitol, triacetin, aromatic hydrocarbons, dearomatized aliphatic compounds, alkylbenzene, alkylnaphthalene, ketones, such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentanone, acetate, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate , Tridecyl acetate, and isobornyl acetate, other esters, such as alkylated lactate, dibasic ester, and γ-butyrolactone, and can be linear, branched, saturated or unsaturated Alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isostearyl alcohol, Cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, and benzyl alcohol. Liquid diluents also include glycerides of saturated and unsaturated fatty acids (typically C 6 -C 22 ), such as plant seed and fruit oils (for example, olive oil, castor oil, linseed oil, sesame oil, corn oil ( Corn oil), peanut oil, sunflower oil, grape seed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil and palm kernel oil), animal fats (for example, tallow, lard, lard, cod liver oil) , Fish oil), and their mixtures. Liquid diluents also include alkylated (eg, methylated, ethylated, butylated) fatty acids, where fatty acids can be obtained by hydrolysis of glycerides from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide [Solvent Guide], 2nd Edition, Interscience, New York, 1950.
本發明之固體組成物和液體組成物通常包含一種或多種表面活性劑。當添加到液體中時,表面活性劑(也稱為「表面活性試劑」)通常改變、最經常地降低液體的表面張力。根據表面活性劑分子中的親水和親脂基團的性質,表面活性劑可用作潤濕劑、分散劑、乳化劑或消泡劑。The solid composition and liquid composition of the present invention usually contain one or more surfactants. When added to liquids, surfactants (also called "surface active agents") usually change, most often reduce the surface tension of the liquid. According to the nature of the hydrophilic and lipophilic groups in the surfactant molecule, the surfactant can be used as a wetting agent, dispersant, emulsifier or defoamer.
表面活性劑可以分類為非離子的、陰離子的或陽離子的。可用於本發明組成物之非離子表面活性劑包括但不限於:醇烷氧基化物,諸如基於天然醇和合成醇(其可以是支鏈或直鏈的)並且由醇和環氧乙烷、環氧丙烷、環氧丁烷或它們的混合物製備的醇烷氧基化物;胺乙氧基化物、鏈烷醇醯胺和乙氧基化鏈烷醇醯胺;烷氧基化甘油三酯,諸如乙氧基化的大豆油、蓖麻油和油菜籽油;烷基酚烷氧基化物,諸如辛基酚乙氧基化物、壬基酚乙氧基化物、二壬基酚乙氧基化物和十二烷基酚乙氧基化物(由酚和環氧乙烷、環氧丙烷、環氧丁烷或其混合物製備);由環氧乙烷或環氧丙烷製備的嵌段聚合物和其中末端嵌段由環氧丙烷製備的反式嵌段聚合物;乙氧基化脂肪酸;乙氧基化脂肪酯和油;乙氧基化甲酯;乙氧基化三苯乙烯基酚(包括由環氧乙烷、環氧丙烷、環氧丁烷或其混合物製備的那些);脂肪酸酯、甘油酯、基於羊毛脂的衍生物、多乙氧基化酯(如多乙氧基化脫水山梨糖醇脂肪酸酯、多乙氧基化山梨糖醇脂肪酸酯和多乙氧基化甘油脂肪酸酯);其他脫水山梨糖醇衍生物如脫水山梨糖醇酯;聚合物表面活性劑,諸如無規共聚物、嵌段共聚物、聚乙二醇樹脂(pegs)、接枝或梳形聚合物以及星形聚合物;聚乙二醇脂肪酸酯;矽酮基表面活性劑;和糖衍生物,諸如蔗糖酯、烷基多糖苷和烷基多糖。Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants that can be used in the composition of the present invention include but are not limited to: alcohol alkoxylates, such as based on natural alcohols and synthetic alcohols (which may be branched or linear) and are composed of alcohols, ethylene oxide, epoxy Alcohol alkoxylates prepared from propane, butylene oxide, or mixtures thereof; amine ethoxylates, alkanol amides, and ethoxylated alkanol amides; alkoxylated triglycerides, such as ethyl Oxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and twelve Alkylphenol ethoxylates (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide or their mixtures); block polymers prepared from ethylene oxide or propylene oxide and their end blocks Trans-block polymers prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyryl phenols (including ethoxylated tristyryl phenols) Alkanes, propylene oxide, butylene oxide or those prepared from mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters (such as polyethoxylated sorbitan fat Acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters); other sorbitan derivatives such as sorbitan esters; polymer surfactants, such as random copolymers Polymers, block copolymers, polyethylene glycol resins (pegs), grafted or comb polymers, and star polymers; polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives, such as Sucrose esters, alkyl polyglycosides and alkyl polysaccharides.
有用的陰離子表面活性劑包括但不限於:烷基芳基磺酸及其鹽;羧化的醇或烷基酚乙氧基化物;二苯基磺酸酯衍生物;木質素和木質素衍生物,諸如木質素磺酸鹽;順丁烯二酸或琥珀酸或它們的酸酐;烯烴磺酸酯;磷酸酯,諸如醇烷氧基化物的磷酸酯,烷基酚烷氧基化物的磷酸酯和苯乙烯基酚乙氧基化物的磷酸酯;基於蛋白質的表面活性劑;肌胺酸衍生物;苯乙烯基酚醚硫酸鹽;油和脂肪酸的硫酸鹽和磺酸鹽;乙氧基化烷基酚的硫酸鹽和磺酸鹽;醇的硫酸鹽;乙氧基化醇的硫酸鹽;胺和醯胺的磺酸鹽,諸如N ,N -烷基牛磺酸鹽;苯、異丙苯、甲苯、二甲苯以及十二烷基苯和十三烷基苯的磺酸鹽;縮聚萘的磺酸鹽;萘和烷基萘的磺酸鹽;分餾石油的磺酸鹽;磺基琥珀醯胺酸鹽;以及磺基琥珀酸鹽和它們的衍生物,諸如二烷基磺基琥珀酸鹽。Useful anionic surfactants include, but are not limited to: alkyl aryl sulfonic acids and their salts; carboxylated alcohol or alkyl phenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives , Such as lignosulfonate; maleic acid or succinic acid or their anhydrides; olefin sulfonate; phosphoric acid ester, such as alcohol alkoxylate phosphate, alkylphenol alkoxylate phosphate and Phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; ethoxylated alkyl groups Sulfates and sulfonates of phenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides, such as N , N -alkyl taurates; benzene, cumene, Sulfonates of toluene, xylene, dodecylbenzene and tridecylbenzene; sulfonates of polycondensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of fractionated petroleum; sulfosuccinamide Acid salts; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinates.
有用的陽離子表面活性劑包括但不限於:醯胺和乙氧基化醯胺;胺諸如N -烷基丙二胺、三伸丙基三胺和二伸丙基四胺,和乙氧基化胺、乙氧基化二胺以及丙氧基化胺(由胺和環氧乙烷、環氧丙烷、環氧丁烷或它們的混合物製備);胺鹽如乙酸銨和二胺鹽;季銨鹽如季鹽、乙氧基化季鹽和二季鹽;以及胺氧化物,諸如烷基二甲基胺氧化物和雙-(2-羥乙基)-烷基胺氧化物。Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N -alkylpropylene diamine, tripropylene triamine and dipropylene tetramine, and ethoxylated Amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide or their mixtures); amine salts such as ammonium acetate and diamine salts; quaternary ammonium Salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxide and bis-(2-hydroxyethyl)-alkylamine oxide.
還可用於本發明組成物的為非離子表面活性劑和陰離子表面活性劑的混合物、或非離子表面活性劑和陽離子表面活性劑之混合物。非離子表面活性劑、陰離子表面活性劑和陽離子表面活性劑及其推薦用途在多個已公佈的參考文獻中揭露,該等參考文獻包括McCutcheon分部,The Manufacturing Confectioner Publishing Co. [糖果製造商出版公司]出版的McCutcheon’s Emulsifiers and Detergents [McCutcheon的乳化劑和洗滌劑],annual American and International Editions [美國和國際年度版];Sisely和Wood,Encyclopedia of Surface Active Agents [表面活性劑百科全書],Chemical Publ. Co.,Inc. [化工出版社有限公司],紐約,1964;以及A. S. Davidson和B. Milwidsky,Synthetic Detergents [合成洗滌劑],第七版,約翰威利父子出版社,紐約,1987。What can also be used in the composition of the present invention is a mixture of a nonionic surfactant and an anionic surfactant, or a mixture of a nonionic surfactant and a cationic surfactant. Nonionic surfactants, anionic surfactants and cationic surfactants and their recommended uses are disclosed in a number of published references, including McCutcheon Division, The Manufacturing Confectioner Publishing Co. [Candy Manufacturer’s Publishing Company] McCutcheon's Emulsifiers and Detergents [McCutcheon's emulsifiers and detergents], annual American and International Editions [American and International Annual Editions]; Sisely and Wood, Encyclopedia of Surface Active Agents [Surface Active Agents Encyclopedia], Chemical Publ Co., Inc. [Chemical Press Co., Ltd.], New York, 1964; and AS Davidson and B. Milwidsky, Synthetic Detergents [Synthetic Detergents], seventh edition, John Wiley & Sons Press, New York, 1987.
本發明之組成物還可包含本領域技術者已知為輔助配製物的配製物助劑和添加劑(其中一些也可被認為是起到固體稀釋劑、液體稀釋劑或表面活性劑作用)。此類配製物助劑和添加劑可控制:pH(緩衝劑)、加工過程中的起泡(消泡劑,諸如聚有機矽氧烷)、活性成分的沈降(懸浮劑)、黏度(觸變增稠劑)、容器內的微生物生長(抗微生物劑)、產品冷凍(防凍劑)、顏色(染料/顏料分散體)、洗脫(成膜劑或黏著劑)、蒸發(蒸發阻斷劑)、以及其他配製物屬性。成膜劑包括例如聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯啶酮-乙酸乙烯酯共聚物、聚乙烯醇、聚乙烯醇共聚物和蠟。配製物助劑和添加劑的實例包括由McCutcheon的分部,The Manufacturing Confectioner Publishing Co.出版的McCutcheon的第2卷:Functional Materials [功能材料],國際和北美年度版;以及PCT揭露號WO 03/024222中列出的那些。The composition of the present invention may also contain formulation auxiliaries and additives known to those skilled in the art as auxiliary formulations (some of which may also be considered to function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives can control: pH (buffering agent), foaming during processing (defoaming agent, such as polyorganosiloxane), sedimentation of active ingredients (suspending agent), viscosity (thixotropic increase) Thickener), microbial growth in the container (antimicrobial agent), product freezing (antifreeze), color (dye/pigment dispersion), elution (film former or adhesive), evaporation (evaporation blocker), And other formulation attributes. The film forming agent includes, for example, polyvinyl acetate, polyvinyl acetate copolymer, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohol, polyvinyl alcohol copolymer, and wax. Examples of formulation auxiliaries and additives include McCutcheon's Vol. 2 published by The Manufacturing Confectioner Publishing Co., a division of McCutcheon: Functional Materials, International and North American Annual Edition; and PCT Publication No. WO 03/024222 Those listed in.
通常藉由將活性成分溶於溶劑中或者藉由在液體或乾稀釋劑中研磨將具有化學式一之化合物和任何其他活性成分結合到本發明組成物中。可藉由簡單地混合該等成分來製備包括可乳化的濃縮物的溶液。如果旨在用作可乳化的濃縮物的液體組成物的溶劑係與水不混溶的,通常加入乳化劑以使含有活性成分的溶劑在用水稀釋時乳化。粒徑高達2000微米(μm)的活性成分漿料可以使用介質研磨機進行濕法研磨,以得到平均粒徑低於3 μm之顆粒。水性漿液可以製成成品懸浮液濃縮物(參見,例如,U.S. 3,060,084)或藉由噴霧乾燥進一步加工以形成水可分散性顆粒劑。無水配製物通常需要無水研磨過程,其產生在2 μm至10 μm範圍內的平均粒徑。粉劑和粉末可以藉由共混並且通常藉由研磨(例如用錘磨機或流能磨)來製備。可藉由將活性物質噴霧在預成形的顆粒劑載體上或者藉由附聚技術來製備顆粒劑和小丸劑。參見,Browning,「Agglomeration [附聚]」,Chemical Engineering [化學工程],1967年12月4日,第147-48頁;Perry’s Chemical Engineer’s Handbook [佩里化學工程師手冊],第4版,McGraw-Hill [麥格勞希爾集團],紐約,1963,第8-57頁及其後頁,以及WO 91/13546。小丸劑可以如U.S. 4,172,714中所述製備。水可分散性和水溶性顆粒劑可如在U.S. 4,144,050、U.S. 3,920,442和DE 3,246,493中傳授的來製備。片劑可以如在U.S. 5,180,587、U.S. 5,232,701和U.S. 5,208,030中所傳授的來製備。膜可以如在GB 2,095,558和U.S. 3,299,566中所傳授的來製備。The compound of Formula One and any other active ingredients are usually incorporated into the composition of the present invention by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent system intended for the liquid composition of the emulsifiable concentrate is immiscible with water, an emulsifier is usually added to emulsify the solvent containing the active ingredient when diluted with water. Active ingredient slurries with a particle size of up to 2000 microns (μm) can be wet-milled using a media grinder to obtain particles with an average particle size of less than 3 μm. The aqueous slurry can be made into a finished suspension concentrate (see, for example, US 3,060,084) or further processed by spray drying to form water-dispersible granules. Anhydrous formulations generally require an anhydrous milling process, which produces an average particle size in the range of 2 μm to 10 μm. Dusts and powders can be prepared by blending and usually by grinding (for example, with a hammer mill or a fluid energy mill). Granules and pellets can be prepared by spraying the active substance on a preformed granular carrier or by agglomeration techniques. See, Browning, "Agglomeration [agglomeration]", Chemical Engineering , December 4, 1967, pages 147-48; Perry's Chemical Engineer's Handbook , 4th edition, McGraw- Hill [McGraw Hill Group], New York, 1963, pages 8-57 and after, and WO 91/13546. Pellets can be prepared as described in US 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in US 4,144,050, US 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in US 5,180,587, US 5,232,701 and US 5,208,030. The membrane can be prepared as taught in GB 2,095,558 and US 3,299,566.
關於配製物領域的進一步訊息,參見T. S. Woods,Pesticide Chemistry and Bioscience, The Food-Environment Challenge [農藥化學與生物科學,食品與環境挑戰]中的「The Formulator’s Toolbox - Product Forms for Modern Agriculture [製劑工具箱 - 現代農業產品形式]」,T. Brooks和T. R. Roberts編輯,Proceedings of the 9th International Congress on Pesticide Chemistry [第九屆農藥化學國際會議論文集],The Royal Society of Chemistry [皇家化學學會],劍橋,1999,第120-133頁。還可參見U.S. 3,235,361,第6欄,第16行至第7欄,第19行和實例10-41;U.S 3,309,192,第5欄,第43行至第7欄,第62行和實例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;U.S. 2,891,855,第3欄,第66行至第5欄,第17行和實例1-4;Klingman,Weed Control as a Science [雜草控制科學],約翰威利父子公司(John Wiley and Sons, Inc.),紐約,1961,第81-96頁;Hance等人,Weed Control Handbook [雜草控制手冊],第8版,Blackwell Scientific Publications [布萊克威爾科學出版社],牛津,1989;和Developments in formulation technology [配製物技術的發展],PJB出版公司(PJB Publications),里士滿,英國,2000。For further information in the field of formulations, see "The Formulator's Toolbox-Product Forms for Modern Agriculture" in TS Woods, Pesticide Chemistry and Bioscience, The Food-Environment Challenge. -Modern Agricultural Product Forms]", edited by T. Brooks and TR Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry [Proceedings of the 9th International Congress on Pesticide Chemistry], The Royal Society of Chemistry [Royal Society of Chemistry], Cambridge, 1999, pp. 120-133. See also US 3,235,361, column 6, lines 16 to 7, lines 19 and Examples 10-41; US 3,309,192, column 5, lines 43 to 7, lines 62 and Examples 8, 12 , 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US 2,891,855, column 3, row 66 to column 5, row 17 and Examples 1-4; Klingman, Weed Control as a Science , John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook [Weed Control Manual], 8th edition, Blackwell Scientific Publications [Blackwell Scientific Press], Oxford, 1989; and Developments in formulation technology [Developments in formulation technology], PJB Publications, in Richmond, United Kingdom, 2000.
因此,該等本發明之化合物和組成物在農業上可用於保護大田作物免受寄生線蟲之侵害,並且還非農業地用於保護其他園藝作物和植物免受植食性寄生線蟲的侵害。該效用包括保護藉由遺傳工程(即轉基因的)引入或者由誘變修飾的遺傳物質以提供有利的性狀的作物和其他植物(即農學和非農學的)。此類性狀的實例包括耐除草劑、耐植食性有害生物(例如昆蟲、蟎、蚜蟲、蜘蛛、線蟲、蝸牛、植物致病真菌、細菌和病毒)、改進的植物生長、對不良生長條件如高溫和低溫、高或低的土壤濕度以及高鹽度的提高的耐受性、增加的開花或結果、更高的收穫產量、更快成熟、收穫產品的更髙品質和/或營養價值、或收穫產品的改善的儲存或加工特性。轉基因植物可以經修飾以表現多種性狀。含有由基因工程或誘變提供的性狀的植物的實例包括表現殺蟲蘇力菌毒素的各種玉米、棉花、大豆和馬鈴薯如YIELD GARD® 、KNOCKOUT® 、STARLINK® 、BOLLGARD® 、NuCOTN® 和NEWLEAF® 、INVICTA RR2 PROTM ,和耐受除草劑的各種玉米、棉花、大豆和油菜籽如ROUNDUP READY® 、LIBERTY LINK® 、IMI® 、STS® 、和CLEARFIELD® ,以及表現N -乙醯基轉移酶(GAT)以提供對草甘膦除草劑的抗性之作物,或含有提供對抑制乙醯乳酸合成酶(ALS)的除草劑之抗性的HRA基因之作物。本發明之化合物和組成物可以與藉由基因工程引入或藉由誘變修飾的性狀協同地相互作用,從而增強性狀的表現型表現或有效性或者提高本發明之化合物和組成物的寄生線蟲控制有效性。特別地,本發明之化合物和組成物可以與蛋白質或對寄生線蟲有毒的其他天然產品的表現型表現協同地相互作用,以提供對該等有害生物的高於加合的控制。Therefore, the compounds and compositions of the present invention can be used in agriculture to protect field crops from parasitic nematodes, and also in non-agricultural applications to protect other horticultural crops and plants from phytophagous parasitic nematodes. This utility includes the protection of crops and other plants (ie, agronomic and non-agricultural) that have been introduced by genetic engineering (ie, transgenic) or genetic material modified by mutagenesis to provide beneficial traits. Examples of such traits include resistance to herbicides, resistance to herbivorous pests (such as insects, mites, aphids, spiders, nematodes, snails, phytopathogenic fungi, bacteria, and viruses), improved plant growth, resistance to adverse growth conditions such as high temperatures And low temperature, high or low soil moisture and increased tolerance of high salinity, increased flowering or fruiting, higher harvest yield, faster maturity, higher quality and/or nutritional value of the harvested product, or harvest Improved storage or processing characteristics of the product. Transgenic plants can be modified to exhibit multiple traits. Examples of plants containing traits provided by genetic engineering or mutagenesis include various corn, cotton, soybeans, and potatoes that exhibit suridin toxins such as YIELD GARD ® , KNOCKOUT ® , STARLINK ® , BOLLGARD ® , NuCOTN ® and NEWLEAF ® , INVICTA RR2 PRO TM , and various herbicide-tolerant corn, cotton, soybeans and rapeseeds such as ROUNDUP READY ® , LIBERTY LINK ® , IMI ® , STS ® , and CLEARFIELD ® , and express N -acetyltransferase ( GAT) crops that provide resistance to glyphosate herbicides, or crops that contain HRA genes that provide resistance to herbicides that inhibit acetolactate synthase (ALS). The compounds and compositions of the present invention can interact synergistically with traits introduced by genetic engineering or modified by mutagenesis, thereby enhancing the phenotypic performance or effectiveness of the traits or enhancing the parasitic nematode control of the compounds and compositions of the invention Effectiveness. In particular, the compounds and compositions of the present invention can synergistically interact with the phenotypic performance of proteins or other natural products that are toxic to parasitic nematodes to provide higher than additive control of these harmful organisms.
本發明之組成物還可以視需要包含植物營養素,例如,包含至少一種選自氮、磷、鉀、硫、鈣、鎂、鐵、銅、硼、錳、鋅和鉬的植物營養素的肥料組成物。值得注意的是包含至少一種肥料組成物的組成物,該肥料組成物包含至少一種選自氮、磷、鉀、硫、鈣和鎂的植物營養素。本發明之進一步包含至少一種植物營養素的組成物可以是呈液體或固體之形式。值得注意的是呈顆粒、小棒或片劑形式的固體配製物。包含肥料組成物的固體配製物可以藉由將本發明之化合物或組成物與該肥料組成物和配製成分一起混合並且然後藉由諸如造粒或擠出的方法製備配製物來製備。可替代地,固體配製物可以藉由將本發明之化合物或組成物在揮發性溶劑中的溶液或懸浮液噴霧到以前製備的呈尺寸穩定的混合物形式(例如,顆粒、小棒或片劑)的肥料組成物上,並且然後蒸發溶劑來製備。The composition of the present invention may also contain phytonutrients as needed, for example, a fertilizer composition containing at least one phytonutrient selected from the group consisting of nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc and molybdenum . It is worth noting that a composition comprising at least one fertilizer composition, the fertilizer composition comprising at least one phytonutrient selected from the group consisting of nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium. The composition of the present invention further comprising at least one phytonutrient may be in liquid or solid form. Of note are solid formulations in the form of granules, small sticks or tablets. A solid formulation containing a fertilizer composition can be prepared by mixing the compound or composition of the present invention with the fertilizer composition and formulation ingredients and then preparing the formulation by a method such as pelletizing or extrusion. Alternatively, the solid formulation can be prepared by spraying a solution or suspension of the compound or composition of the present invention in a volatile solvent into a previously prepared mixture in the form of a dimensionally stable mixture (eg, granules, small sticks or tablets) On the fertilizer composition, and then evaporate the solvent to prepare.
本發明之化合物可以表現出對廣譜寄生線蟲的活性,該等廣譜寄生線蟲在植物(例如,葉子、果實、莖、根或種子)或動物和人類(例如,血管或消化系統或其他組織)內部生活或生長或以該等為食並且因此損害正在生長的和儲存的農作物、林業、溫室作物、觀賞植物和苗圃作物,或損害動物和人類健康。特別的目的作物係結果蔬菜,例如茄科和葫蘆科作物,種植作物如香蕉和咖啡,塊根作物如馬鈴薯、洋蔥和胡蘿蔔,以及大田作物如煙草、花生、棉花、甘蔗和大豆。The compounds of the present invention can exhibit activity against a broad spectrum of parasitic nematodes, which are found in plants (for example, leaves, fruits, stems, roots or seeds) or animals and humans (for example, blood vessels or digestive systems or other tissues). ) Living or growing internally or feeding on them and thus damage the growing and stored crops, forestry, greenhouse crops, ornamental plants and nursery crops, or damage the health of animals and humans. Special target crops are fruit vegetables, such as Solanaceae and Cucurbitaceae crops, planted crops such as bananas and coffee, root crops such as potatoes, onions and carrots, and field crops such as tobacco, peanuts, cotton, sugarcane and soybeans.
本發明之化合物可以對線蟲門的有腺綱和胞管腎綱的成員具有活性,該等成員包括嘴刺目、矛線目、小桿目、圓線蟲目、蛔目、尖尾目(Oxyurida)、旋尾目、墊刃目和滑刃目的經濟上重要的成員,例如但是不限於經濟上重要的農業有害生物,例如根結線蟲屬的根結線蟲、異皮線蟲屬和球異皮線蟲屬的胞囊線蟲、短體線蟲屬(Pratylenchus )的根腐病線蟲(lesion nematode)、腎狀線蟲屬的腎形線蟲(reniform nematode)、穿孔線蟲屬(Radopholus )的掘穴線蟲(burrowing nematode)、刺線蟲屬(Belonolaimus )的刺線蟲、螺旋線蟲屬(Helicotylenchus )和盾線蟲屬(Scutellonema )的螺旋線蟲、半穿刺線蟲屬(Tylenchulus )的柑橘半穿刺線蟲(citrus nematode)、毛刺線蟲屬(Trichodorus )和擬毛刺線蟲屬(Paratrichodorus )的短粗根線蟲(stubby root nematode)、劍線蟲屬(Xiphinema )的劍線蟲、矮化線蟲屬(Tylenchorhynchus )的矮化線蟲、長針線蟲屬(Longidorus )和擬長針屬(Paralongidorus )的長針線蟲、槍線蟲屬(Hoplolaimus )的矛線蟲、環線蟲科的環線蟲、莖線蟲屬(Ditylenchus )和粒線蟲屬(Anguina )的莖線蟲、和滑刃線蟲屬(Aphelenchoides )和細桿滑刃線蟲屬(Rhadinaphelenchus )的葉線蟲/莖線蟲;以及對動物和人類健康寄生蟲(即,經濟上重要的蛔蟲例如馬體內的普通圓線蟲、狗體內的犬蛔蟲(Toxocara canis )、綿羊體內的撚轉血矛線蟲(Haemonchus contortus )、狗體內的犬心絲蟲(Dirofilaria immitis ))具有活性。The compounds of the present invention can have activity against members of the Glandularia and Angionephrines of the Nematode phylum, and these members include the Orchididae, the Cylindricale, the Microcariae, the Strongyloides, the Ascaris, and the Oxyurida (Oxyurida), Economically important members of the order Trichocera, Diabolus, and Slipblade, such as, but not limited to, economically important agricultural pests, such as Root-knot nematodes of the genus Root-knot nematodes, Heterodera spp., and cells of the genus Heterodermata Burrowing nematode, the root rot nematode of the genus Pratylenchus, the reniform nematode of the genus Reniform nematode, the burrowing nematode of the Radopholus genus, and the spiny nematode genus (Belonolaimus) of Heteraxine, spiral nematode genera (of Helicotylenchus) and shield Strongyloides (Scutellonema) spiral nematodes, Tylenchulus semipenetrans genus (Tylenchulus) citrus Tylenchulus semipenetrans (citrus nematode), Trichodorus genus (, Trichodorus) and Quasi Paratrichodorus stubby root nematode, Xiphinema Xiphinema , Tylenchorhynchus dwarf nematode, Longidorus and Longidorus Paralongidorus, Hoplolaimus ( Hoplolaimus ), Ringworm, Ditylenchus and Anguina , Ditylenchus and Anguina, and Aphelenchoides and thin Leaf nematodes/Ditylenchus of the genus Rhadinaphelenchus; and parasites to animal and human health (ie, economically important roundworms such as the common strongyloides in horses, Toxocara canis in dogs, and sheep Haemonchus contortus in the body and Dirofilaria immitis in dogs are active.
值得注意的是本發明之化合物用於控制南方根結線蟲(southern root-knot nematode,Meloidogyne incognita )之用途。本領域技術者將理解,並不是所有的化合物對所有線蟲的所有生長階段都同等有效。It is worth noting that the compound of the present invention is used to control southern root-knot nematode ( Meloidogyne incognita ). Those skilled in the art will understand that not all compounds are equally effective for all growth stages of all nematodes.
本發明之化合物還可以具有對以下的成員的活性:扁形動物門、絛蟲綱(絛蟲)和吸蟲綱(吸蟲),包括傷害動物和人類健康的寄生蟲(即,經濟上重要的吸蟲和絛蟲)(例如,馬體內的葉狀裸頭絛蟲(Anoplocephala perfoliata )、反芻動物體內的肝片吸蟲(Fasciola hepatica ))。The compounds of the present invention may also have activity against members of the phylum Platydae, the class of tapeworms (taenia) and the class of trematodes (flukes), including parasites that harm animal and human health (ie, economically important flukes) And tapeworms) (for example, Anoplocephala perfoliata in horses, Fasciola hepatica in ruminants).
本發明之化合物還可與一種或多種其他生物學活性化合物或藥劑混合以形成多組分殺有害生物劑,該殺有害生物劑賦予甚至更廣譜的農學和非農學效用,該生物學活性化合物或試劑包括殺昆蟲劑、殺真菌劑、殺線蟲劑、殺細菌劑、殺蜱蟎亞綱動物劑、除草劑、除草劑安全劑、生長調節劑諸如昆蟲蛻皮抑制劑和生根刺激劑、化學不育劑、化學訊息素、驅蟲劑、引誘劑、訊息素、取食刺激劑、其他生物學活性化合物或昆蟲病原細菌、病毒或真菌。因此,本發明還涉及包含式一 之化合物和有效量之至少一種額外的生物活性化合物或藥劑的組成物,並且還可包含至少一種表面活性劑、固體稀釋劑或液體稀釋劑。對於本發明之混合物,可將其他生物學活性化合物或藥劑與本發明之化合物(包括式一 之化合物)一起配製以形成預混物,或者其他生物學活性化合物或試劑可與本發明之化合物(包括式一 之化合物)分開配製,並且在應用前將兩種配製物組合在一起(例如,在噴霧罐中),或可替代地,依次應用。The compound of the present invention can also be mixed with one or more other biologically active compounds or agents to form a multi-component pesticide which imparts an even broader spectrum of agronomic and non-agronomic effects. The biologically active compound Or reagents include insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulators, chemical compounds Inoculants, chemical message elements, insect repellents, attractants, message elements, feeding stimulants, other biologically active compounds or insect pathogenic bacteria, viruses or fungi. Therefore, the present invention also relates to a composition comprising the compound of Formula One and an effective amount of at least one additional biologically active compound or medicament, and may also comprise at least one surfactant, solid diluent or liquid diluent. For the mixture of the present invention, other biologically active compounds or agents can be formulated with the compounds of the present invention (including the compound of formula one ) to form a premix, or other biologically active compounds or reagents can be combined with the compounds of the present invention ( ( Comprising the compound of formula one) are formulated separately, and the two formulations are combined (for example, in a spray can) before application, or alternatively, applied sequentially.
可以配製本發明之化合物的這種生物學活性化合物或藥劑之實例係殺昆蟲劑,例如阿巴美丁、高滅磷、滅蟎醌、啶蟲脒、氟丙菊酯、啶喃環丙蟲酯([(3S ,4R ,4aR ,6S ,6aS ,12R ,12aS ,12bS )-3-[(環丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氫-6,12-二羥基-4,6a,12b-三甲基-11-側氧基-9-(3-吡啶基)-2H ,11H -萘并[2,1-b ]哌喃并[3,4-e ]哌喃-4-基]甲基環丙烷羧酸酯)、磺胺蟎酯、雙甲脒、阿維菌素(avermectin)、印楝素、穀硫磷、丙硫克百威、殺蟲磺、聯苯菊酯、聯苯肼酯、雙三氟蟲脲、硼酸鹽、噻𠯤酮、硫線磷、西維因、卡巴呋喃、殺螟丹、伐蟲脒、氯蟲苯甲醯胺、溴蟲腈、定蟲隆、毒死蜱、甲基毒死蜱、環蟲醯肼、蟎死淨、噻蟲胺、氰蟲醯胺(3-溴-1-(3-氯-2-吡啶基)-N -[4-氰基-2-甲基-6-[(甲基胺基)羰基]苯基]-1H -吡唑-5-甲醯胺)、環溴蟲醯胺(3-溴-N -[2-溴-4-氯-6-[[(1-環丙基乙基)胺基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H -吡唑-5-甲醯胺)、乙氰菊酯、環氧蟲啶((5S ,8R )-1-[(6-氯-3-吡啶基)甲基]-2,3,5,6,7,8-六氫-9-硝基-5,8-環氧基-1H -咪唑并[1,2-a ]吖呯)、丁氟蟎酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、γ-三氟氯氰菊酯、λ-三氟氯氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、滅蠅胺、溴氰菊酯、丁醚脲、二𠯤農、狄氏劑、二氟脲、四氟甲醚菊酯、殺蟲雙、樂果、呋蟲胺、苯蟲醚、艾瑪菌素、安殺番、高氰戊菊酯、乙蟲腈、依芬普司、乙蟎唑、苯丁錫、殺螟硫磷、苯硫威、苯氧威、甲氰菊酯、氰戊菊酯、氟蟲腈、氟甲氧喹啉(flometoquin)(2-乙基-3,7-二甲基-6-[4-(三氟甲氧基)苯氧基]-4-喹啉基碳酸甲酯)、氟啶蟲醯胺、氟蟲醯胺、氟氰戊菊酯、嘧蟲胺、氟蟲脲、氟菌蟎酯((αE )-2-[[2-氯-4-(三氟甲基)苯氧基]甲基]-α-(甲氧基亞甲基)苯乙酸甲酯)、聯氟碸(5-氯-2-[(3,4,4-三氟-3-丁烯-1-基)磺醯基]噻唑)、氰基硫醚類殺蟲劑(fluhexafon)、氟吡菌醯胺、flupiprole(1-[2,6-二氯-4-(三氟甲基)苯基]-5-[(2-甲基-2-丙烯-1-基)胺基]-4-[(三氟甲基)亞磺醯基]-1H -吡唑-3-甲腈)、氟吡呋喃酮(4-[[(6-氯-3-吡啶基)甲基](2,2-二氟乙基)胺基]-2(5H )呋喃酮)、氟胺氰菊酯、τ-氟胺氰菊酯、地蟲硫磷、伐蟲脒、噻唑磷、氯蟲醯肼、右旋七氟甲醚菊酯(heptafluthrin)(2,2-二甲基-3-[(1Z )-3,3,3-三氟-1-丙烯-1-基]環丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氟鈴脲、噻蟎酮、氟蟻腙、吡蟲啉、茚蟲威、殺蟲皂、異柳磷、虱蟎脲、馬拉硫磷、氯氟醚菊酯((1R ,3S )-3-(2,2-二氯乙烯基)-2,2-二甲基環丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氰氟蟲腙、蝸牛敵、甲胺磷、甲硫威、滅多蟲、甲氧普林、甲氧滴滴涕、甲氧蟲醯肼、甲氧苄氟菊酯、久效磷、單氟醚菊酯(monofluorothrin)(3-(2-氰基-1-丙烯-1-基)-2,2-二甲基環丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、菸鹼、烯啶蟲胺、硝乙脲噻唑、雙苯氟脲、多氟脲、草胺醯、對硫磷、甲基對硫磷、撲滅司林、甲拌磷、伏殺硫磷、亞胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯(profluthrin)、克蟎特、丙苯烴菊酯、吡氟丁醯胺(pyflubumide)(1,3,5-三甲基-N -(2-甲基-1-丙醯)-N -[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H -吡唑-4-甲醯胺)、吡蚜酮、吡𠯤氟蟲腈、除蟲菊酯、嗒蟎靈、啶蟲丙醚、新喹唑啉(間二氮雜苯)類殺昆蟲劑(pyrifluquinazon)、嘧蟎胺((αE )-2-[[[2-[(2,4-二氯苯基)胺基]-6-(三氟甲基)-4-嘧啶基]氧基]甲基]-α-(甲氧基亞甲基)苯乙酸甲酯)、吡啶氟蟲腈、蚊蠅醚、魚藤酮、利阿諾定、氟矽菊酯、乙基多殺菌素、多殺菌素、螺蟎酯、螺甲蟎酯、螺蟲乙酯、硫丙磷、碸蟲啶(N -[甲基氧化[1-[6-(三氟甲基)-3-吡啶基]乙基]-λ4 -磺醯亞基]胺腈)、蟲醯肼、吡蟎胺、伏蟲脲、七氟菊酯、特丁磷、殺蟲畏、似蟲菊、四氟醚菊酯(2,2,3,3-四甲基環丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氟氰蟲醯胺、噻蟲啉、噻蟲𠯤、硫雙威、殺蟲雙、噻㗁唑碸(tioxazafen)(3-苯基-5-(2-噻吩基)-1,2,4-㗁二唑)、唑蟲醯胺、四溴菊酯、唑蚜威、敵百蟲、三氟苯嘧啶(2,4-二側氧基-1-(5-嘧啶基甲基)-3-[3-(三氟甲基)苯基]-2H -吡啶并[1,2-a ]嘧啶陽離子內鹽)、殺蟲隆、蘇力菌δ-內毒素、昆蟲病原細菌、昆蟲病原病毒和昆蟲病原真菌。Examples of such biologically active compounds or agents that can be formulated into the compounds of the present invention are insecticides, such as abamectin, benzodiazepine, acarquinone, acetamiprid, flumethrin, pyripyrim Ester ([(3 S ,4 R ,4a R ,6 S ,6a S ,12 R ,12a S ,12b S )-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a, 5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-pendant oxy-9-(3-pyridyl)-2 H , 11 H -Naphtho[2,1- b ]piperano[3,4- e ]piperan-4-yl]methylcyclopropane carboxylate), sulfadifen, bisformamidine, abamectin (Avermectin), azadirachtin, azinphos, benfuracarb, difenthrin, bifenthrin, bifenazate, diflufenazone, borate, thienone, thionphos, western Vine, carbofuran, salamidine, valfenamidine, chlorantraniliprole, chlorfenapyr, chlorpyrifos, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos, chlorpyrifos, clothianidin, cyanidin Amide (3-bromo-1-(3-chloro-2-pyridyl) -N -[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1 H -Pyrazol-5-carboxamide), cyclofenapyr (3-bromo- N -[2-bromo-4-chloro-6-[[(1-cyclopropylethyl)amino]carbonyl] Phenyl]-1-(3-chloro-2-pyridyl)-1 H -pyrazole-5-carboxamide), cypermethrin, epoxypyridine ((5 S ,8 R )-1- [(6-Chloro-3-pyridyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy-1 H -imidazo[1 ,2- a ]Acridine), butafenofen, cyfluthrin, β-cyfluthrin, cyfluthrin, γ-cypermethrin, λ-cyfluthrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, fly control Amine, deltamethrin, diafenthiuron, diflubenzuron, dieldrin, diflubenzuron, tetrafluthrin, dimethoate, dimethoate, dinotefuran, fenfenthiuron, emamectin, Fenvalerate, fenvalerate, ethiprole, efenprox, etoxazole, fenbutatin, fenthion, fenthiocarb, fenoxycarb, fenvalerate, fenvalerate, Fipronil, flometoquin (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolinyl carbonate Ester), sulfoxaflor, sulforaphane, flufenvalerate, sulfenpyram, flufenoxuron, flufenoxamate ((α E )-2-[[2-chloro-4-(三Fluoromethyl)phenoxy]methyl]-α-(methoxymethylene)phenylacetate), difluorosulfide (5-chloro-2-[(3,4,4-trifluoro-3 -Butene-1-yl)sulfonyl]thiazole), cyanosulfide insecticides (fluhexafon), fluopyram, flupiprole (1-[2,6-two Chloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]- 1 H -pyrazole-3-carbonitrile), fluopyranone (4-[[(6-chloro-3-pyridyl)methyl](2,2-difluoroethyl)amino]-2( 5 H )Furanone), fluvalinone, τ-fluvalinate, fenoxaphos, valfenamidine, thiazophos, chlorfenazone, heptafluthrin (heptafluthrin) ( 2,2-Dimethyl-3-[(1 Z )-3,3,3-trifluoro-1-propen-1-yl]cyclopropanecarboxylic acid [2,3,5,6-tetrafluoro-4 -(Methoxymethyl)phenyl]methyl), flufenuron, thiadione, hydrazine, imidacloprid, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, Cyhalothrin ((1 R ,3 S )-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid [2,3,5,6-tetrafluoro- 4-(Methoxymethyl)phenyl]methyl), Methoxyfluron, Snail Di, Methamidophos, Methiocarb, Metdopyr, Metoprin, Methoxychlor, Methoxyfen, Metofluthrin, monocrotophos, monofluorothrin (3-(2-cyano-1-propen-1-yl)-2,2-dimethylcyclopropane carboxylic acid [2 ,3,5,6-Tetrafluoro-4-(methoxymethyl)phenyl]methyl), nicotine, nitenpyram, nithiazole, diflubenzuron, polyfluorocarbamide, oxamine Phosphorus, parathion, parathion methyl, permethrin, phorate, sulfaphos, imiphos, phosphamide, aphiprocarb, profenofos, profluthrin (profluthrin), gram Mite, profenthrin, pyflubumide (1,3,5-trimethyl- N -(2-methyl-1-propanol) -N -[3-(2- Methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1 H -pyrazole-4-carboxamide ), pymetrozine, fipronil, pyrethrin, pyrethrum, pyrethrum, acetamiprid, new quinazoline (m-diazepine) insecticide (pyrifluquinazon), pyrimethanil (( α E )-2-[[[2-[(2,4-Dichlorophenyl)amino]-6-(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]-α-( Methoxymethylene) methyl phenylacetate), pyridine fipronil, cyprofen, rotenone, rianodine, silfluthrin, spinetoram, spinosyn, spirodiclofen, spiromethicone Dicoxyfen, Spirotetramat, Thioprophos, Sulfoxazone ( N -[Methyl Oxide [1-[6-(Trifluoromethyl)-3-pyridyl]ethyl]-λ 4 -sulfonamide Base] amine nitrile), fenpyrazine, tebufenuron, flubenzuron, tefluthrin, terbufos, diflubenzuron, pyrethrum, perfluthrin (2,2,3,3-tetra Methylcyclopropane carboxylic acid [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl] methyl ester), flufentrazone Amine, thiacloprid, clothianid, thiodicarb, dimehypo, tioxazafen (3-phenyl-5-(2-thienyl)-1,2,4-㗁diazole) , Fentrapyramide, tetrabromothrin, trifluprocarb, trichlorfon, trifluoropyrimidine (2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-( trifluoromethyl) phenyl] -2 H - pyrido [1,2- a] pyrimidin the cation salt), triflumuron, Bacillus thuringiensis, the toxin δ- bacteria, entomopathogenic bacteria, entomopathogenic virus and entomopathogenic fungi .
值得注意的是殺昆蟲劑,諸如阿巴美丁、啶蟲脒、氟丙菊酯、啶喃環丙蟲酯、雙甲脒、阿維菌素、印楝素、丙硫克百威、殺蟲磺、聯苯菊酯、噻𠯤酮、硫線磷、西維因、殺螟丹、氯蟲苯甲醯胺、溴蟲腈、毒死蜱、噻蟲胺、氰蟲醯胺、環溴蟲醯胺、乙氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、γ-三氟氯氰菊酯、λ-三氟氯氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、滅蠅胺、溴氰菊酯、狄氏劑、呋蟲胺、苯蟲醚、艾瑪菌素、安殺番、高氰戊菊酯、乙蟲腈、依芬普司、乙蟎唑、殺螟硫磷、苯硫威、苯氧威、氰戊菊酯、氟蟲腈、氟甲氧喹啉、氟啶蟲醯胺、氟蟲醯胺、氟蟲脲、氟菌蟎酯、聯氟碸、flupiprole、氟吡呋喃酮、氟胺氰菊酯、伐蟲脒、噻唑磷、右旋七氟甲醚菊酯、氟鈴脲、氟蟻腙、吡蟲啉、茚蟲威、虱蟎脲、氯氟醚菊酯、氰氟蟲腙、滅蟲威、滅多蟲、甲氧普林、甲氧蟲醯肼、甲氧苄氟菊酯、單氟醚菊酯、烯啶蟲胺、硝乙脲噻唑、雙苯氟脲、草胺醯、pyflubumide、吡蚜酮、除蟲菊酯、嗒蟎靈、啶蟲丙醚、嘧蟎胺、蚊蠅醚、利阿諾定、乙基多殺菌素、多殺菌素、螺蟎酯、螺甲蟎酯、螺蟲乙酯、碸蟲啶、蟲醯肼、似蟲菊、四氟醚菊酯、噻蟲啉、噻蟲𠯤、硫雙威、殺蟲雙、四溴菊酯、唑蚜威、三氟苯嘧啶、殺鈴脲、蘇力菌δ-內毒素、蘇力菌的所有菌株以及核型多角體病毒的所有毒株。It is worth noting that insecticides, such as abamectin, acetamiprid, fenfluthrin, pyripapyr, amitraz, abamectin, azadirachtin, benfuracarb, and Methoxyfen, bifenthrin, thienanthone, thionphos, carbaryl, fentan, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, chlorfenapyr Amine, cypermethrin, cyfluthrin, β-cypermethrin, cyfluthrin, γ-cypermethrin, λ-cypermethrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, Dichlorfon, dinotefuran, fenthiprole, emamectin, benzodiazepine, fenvalerate, ethiprole, efenprox, etoxazole, fenthion, fenthiocarb, benzene Oxycarb, fenvalerate, fipronil, fluoxyquinoline, sulfoxaflor, sulfipramide, flufenoxuron, flufenoxamate, diflufenazone, flupiprole, fluopyranone, fluorine Telamethrin, Valfenapyr, Thiazophos, D-Sevofluthrin, Fluvalon, Flufenazone, Imidacloprid, Indoxacarb, Lufenuron, Cyfluthrin, Cyhalazone, Dimethocarb, metdopyr, methoprene, methoprene, trifluthrin, monofluthrin, nitenpyram, nithiazole, diflubenzuron, flufenoxan, Pyflubumide, pymetrozine, pyrethrum, pyrethrum, pyraclosporin, pyrimethanil, pyrenac, rianodine, spinetoram, spinosyn, spirodiclofen, spiromali Ester, Spirotetramat, Susifoxapyr, Tebufenozide, Pyrethrum, Perfluthrin, Thiacloprid, Clothiadin, Thiodicarb, Dimehypo, Permethrin, Tanzapicarb, Trifluorophenyl pyrimidine, triflumuron, sulzeri delta-endotoxin, all strains of sulzeri, and all strains of nuclear polyhedrosis virus.
用於與本發明之化合物混合的生物製劑的一個實施方式包括昆蟲病原細菌諸如蘇力菌,和膠囊包封的蘇力菌的δ-內毒素諸如由CellCap® 方法製備的MVP® 和MVPII® 生物殺昆蟲劑(CellCap® 、MVP® 和MVPII® 是Mycogen公司,印弟安納波里斯,印第安那州,美國的商標);昆蟲病原真菌諸如綠僵菌;和昆蟲病原(天然存在的和遺傳修飾的二者)病毒,包括桿狀病毒、核型多角體病毒(NPV)諸如穀實夜蛾(Helicoverpa zea )核型多角體病毒(HzNPV)、芹菜夜蛾(Anagrapha falcifera )核型多角體病毒(AfNPV);和顆粒體病毒(GV),諸如蘋果蠹蛾(Cydia pomonella )顆粒體病毒(CpGV)。One embodiment of the biological preparation used for mixing with the compound of the present invention includes insect pathogenic bacteria such as Suribus, and encapsulated delta-endotoxin of Suribus such as MVP ® and MVPII ® prepared by the CellCap ® method. Insecticides (CellCap ® , MVP ® and MVPII ® are trademarks of Mycogen, Indianapolis, Indiana, USA); insect pathogenic fungi such as Metarhizium anisopliae; and insect pathogens (naturally occurring and genetically modified two Viruses, including baculovirus, nuclear polyhedrosis virus (NPV) such as Helicoverpa zea nuclear polyhedrosis virus (HzNPV), celery armyworm ( Anagrapha falcifera ) nuclear polyhedrosis virus (AfNPV) ; And granulovirus (GV), such as codling moth ( Cydia pomonella ) granulovirus (CpGV).
特別值得注意的是其中其他無脊椎有害生物防治活性成分屬於與式一之化合物不同的化學類別或者具有與其不同的作用位點之組合。在某些情況下,與至少一種具有相似控制範圍但是不同作用位點的其他無脊椎有害生物防治活性成分的組合對於抗性管理將是特別有利的。因此,本發明之組成物可進一步包含至少一種額外地無脊椎有害生物控制活性成分,該活性成分具有類似的控制範圍,但是屬於不同的化學類別或者具有不同的作用位點。該等額外的生物學活性化合物或藥劑包括但不限於乙醯膽鹼酯酶(AChE)抑制劑,諸如胺基甲酸酯類的滅多蟲、草胺醯、硫雙威、唑蚜威,和有機磷酸酯類的毒死蜱;GABA閘控氯離子通道拮抗劑,諸如環戊二烯類的狄氏劑和安殺番,以及苯基吡唑類的乙蟲腈和氟蟲腈;鈉通道調節劑,諸如擬除蟲菊酯類的聯苯菊酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、λ-三氟氯氰菊酯、氯氰菊酯、溴氰菊酯、四氟甲醚菊酯、高氰戊菊酯、甲氧苄氟菊酯和丙氟菊酯;菸鹼型乙醯膽鹼受體(nAChR)促效劑,諸如新菸鹼類的啶蟲脒、噻蟲胺、呋蟲胺、吡蟲啉、烯啶蟲胺、硝乙脲噻唑、噻蟲啉和噻蟲𠯤、以及碸蟲啶;菸鹼型乙醯膽鹼受體(nAChR)變構活化劑,諸如多殺菌黴素類的乙基多殺菌素和多殺菌素;氯離子通道活化劑,諸如阿維菌素類的阿巴美丁和艾瑪菌素;保幼激素模擬物,諸如苯蟲醚、甲氧普林、苯氧威和蚊蠅醚;選擇性同翅目取食阻斷劑,諸如吡蚜酮和氟啶蟲醯胺;蟎生長抑制劑,諸如乙蟎唑;粒線體ATP合成酶抑制劑,諸如克蟎特;經由破壞質子梯度而產生的氧化性磷酸化的解偶合劑,諸如溴蟲腈;菸鹼型乙醯膽鹼受體(nAChR)通道阻斷劑,諸如沙蠶毒素(nereistoxin)類似物殺螟丹;殼多糖生物合成抑制劑,諸如苯甲醯脲類的氟蟲脲、氟鈴脲、虱蟎脲、雙苯氟脲、多氟脲和殺鈴脲、以及噻𠯤酮;雙翅目蛻皮干擾劑,諸如滅蠅胺;蛻皮激素受體促效劑,諸如雙醯肼類的甲氧蟲醯肼和蟲醯肼;真蛸胺受體促效劑,諸如雙甲脒;粒線體複合體III電子傳遞抑制劑,諸如氟蟻腙;粒線體複合體I電子傳遞抑制劑,諸如嗒蟎靈;電壓依賴型鈉通道阻斷劑,諸如茚蟲威;乙醯CoA羧化酶的抑制劑,諸如季酮酸和特特拉姆酸(tetramic acid)類的螺蟎酯、螺甲蟎酯和螺蟲乙酯;粒線體複合體II電子傳遞抑制劑,諸如ß-酮腈類的腈吡蟎酯和丁氟蟎酯;ryanidine受體調節劑,諸如胺茴酸二醯胺類的氯蟲苯甲醯胺、氰蟲醯胺和氰蟲醯胺,二醯胺類,諸如氟蟲雙醯胺,和利阿諾定受體配位基,諸如利阿諾定;其中負責生物活性的靶位點未知或未被表徵的化合物,諸如印楝素、聯苯肼酯、啶蟲丙醚、新喹唑啉(間二氮雜苯)類殺蟲劑(pyrifluquinazon)和三氟苯嘧啶;昆蟲中腸膜微生物干擾劑,諸如蘇力菌和它們產生的δ-內毒素以及球形芽孢桿菌;和生物藥劑,包括核多角形病毒(NPV)以及其他天然存在的或遺傳修飾的殺昆蟲病毒。It is particularly noteworthy that the other invertebrate pest control active ingredients belong to a different chemical class from the compound of Formula One or have a combination of different sites of action. In some cases, a combination with at least one other invertebrate pest control active ingredient having a similar control range but different action sites will be particularly advantageous for resistance management. Therefore, the composition of the present invention may further comprise at least one additional invertebrate pest control active ingredient, which has a similar control range but belongs to a different chemical category or has a different site of action. Such additional biologically active compounds or agents include, but are not limited to, acetylcholinesterase (AChE) inhibitors, such as carbamate-type methafen, acetaminophen, thiodicarb, pyrazocarb, and organic Phosphate esters of chlorpyrifos; GABA gated chloride channel antagonists, such as cyclopentadiene-based dieldrin and azuridine, and phenylpyrazoles such as ethiprole and fipronil; sodium channel modulators, Bifenthrin such as pyrethroids, cyfluthrin, β-cyfluthrin, cyfluthrin, lambda cyhalothrin, cypermethrin, deltamethrin, permethrin, fenvalerate , Trifluthrin and profluthrin; nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoid acetamiprid, clothianidin, dinotefuran, imidacloprid, ene Acetamiprid, Nitridithiazole, Thiacloprid and clothianidin, as well as Selenox; nicotinic acetylcholine receptor (nAChR) allosteric activators, such as spinosad like spinetoram And spinosyn; chloride channel activators, such as abamectin and emamectin of the abamectin class; juvenile hormone mimics, such as fenfenpyr, methoprene, fenoxycarb and mosquitoes Cyclofenac; selective homopteran feeding blockers, such as pymetrozine and flufenamid; mite growth inhibitors, such as etoxazole; mitochondrial ATP synthase inhibitors, such as mitoxate; via Discoupling agents for oxidative phosphorylation that disrupt the proton gradient, such as chlorfenapyr; nicotinic acetylcholine receptor (nAChR) channel blockers, such as nereistoxin analogs, saccharin; Chitin biosynthesis inhibitors, such as flufenoxuron, flufenuron, lufenuron, diflubenzuron, flufenuron and triflumuron, as well as thiophene; Diptera molting interfering agent , Such as cyromazine; ecdysone receptor agonists, such as dimethicone and fenthiazole; true cyromidine receptor agonists, such as methamidine; mitochondrial complex III electrons Delivery inhibitors, such as hydrazone; mitochondrial complex I electron transport inhibitors, such as mitazin; voltage-dependent sodium channel blockers, such as indoxacarb; inhibitors of acetyl-CoA carboxylase, such as Quaternary acid and tetramic acid (spirodicofen, spiromesifen, and spirotetramat); mitochondrial complex II electron transport inhibitors, such as the ß-ketonitrile class of pyridoxine Esters and fluflufenox; ryanidine receptor modulators, such as chlorantraniliprole, cyantraniliprole, and cyantraniliprole, diamides, such as sulfipramide , And rianodine receptor ligands, such as rianodine; compounds in which the target site responsible for biological activity is unknown or uncharacterized, such as azadirachtin, bifenazate, acetamiprid, new Quinazolines (pyrifluquinazon) and trifluorophenyl pyrimidines; insect midgut membrane microbial disruptors, such as sulei bacteria and the delta-endotoxin they produce, and Bacillus sphaericus; and biological Medicaments, including nuclear polyhedrosis virus (NPV) and other naturally occurring or genetically modified insecticidal viruses.
可用本發明之化合物配製的生物學活性化合物或試劑的另外的實例是:殺真菌劑,諸如阿拉酸式苯-S-甲基、4-十二烷基-2,6-二甲基𠰌啉(aldimorph)、唑嘧菌胺、安美速、敵菌靈、戊環唑、嘧菌酯、苯霜靈(包括精苯霜靈)、麥鏽靈、苯菌靈、苯噻菌胺(benthiavalicarb)(包括苯噻菌胺(benthiavalicarb-isopropyl))、苯并烯氟菌唑(benzovindiflupyr)、3-苯并[b]噻吩-2-基-5,6-二氫-1,4,2-噻𠯤 4-氧化物(bethoxazin)、樂殺蟎、聯苯、聯苯三唑醇、聯苯吡菌胺、滅瘟素、啶醯菌胺、糠菌唑、乙嘧酚磺酸酯、丁賽特、萎鏽靈、環丙醯菌胺、敵菌丹、克菌丹、多菌靈、地茂散、百菌清、乙菌利、氫氧化銅、氧氯化銅、硫酸銅、丁香菌酯、氰霜唑、環氟菌胺、霜脲氰、環唑醇、嘧菌環胺、抑菌靈、雙氯氰菌胺、嗒菌清、氯硝胺、乙黴威、惡醚唑、二氟林、甲菌定、烯醯𠰌啉、醚菌胺、烯唑醇(包括烯唑醇-M)、敵蟎普、二噻農、二硫戊環、十二環𠰌啉、多果定、益康唑、乙環唑、敵瘟磷、enoxastrobin(還被稱為enestroburin(烯肟菌酯))、氟環唑、噻唑菌胺、乙菌定、土菌靈、㗁唑菌酮、咪唑菌酮、烯肟菌胺、氯苯嘧啶醇、腈苯唑、甲呋醯苯胺、環醯菌胺、氰菌胺、拌種咯、苯鏽啶、丁苯𠰌啉、胺苯吡菌酮、三苯基乙酸錫、三苯基氫氧化錫、福美鐵、嘧菌腙、氟甲氧喹啉、氟啶胺、咯菌腈、氟菌蟎酯、氟𠰌啉、氟吡菌胺、氟吡菌醯胺、氟嘧菌酯、氟喹唑、氟矽唑、磺菌胺、氟噻菌淨(flutianil)、氟醯胺、粉唑醇、氟唑菌醯胺、滅菌丹、四氯苯酞(還被稱為苯酞)、麥穗寧、呋霜靈、福拉比、己唑醇、惡黴靈、雙胍鹽、抑黴唑、醯胺唑、醯胺唑、烷苯磺酸鹽標準品、雙胍辛胺三乙酸鹽、iodicarb、種菌唑、異丙噻菌胺(isofetamid)、異稻瘟淨、異菌脲、丙森鋅、稻瘟靈、吡唑萘菌胺、異噻菌胺、春雷黴素、克收欣、代森錳鋅、雙炔醯菌胺、mandestrobin、代森錳、mapanipyrin、滅鏽胺、消蟎多、甲霜靈(包括高效甲霜靈/精甲霜靈)、葉菌唑、磺菌威、代森聯、苯氧菌胺、苯菌酮、腈菌唑、萘替芬(naftitine)、甲胂鐵銨(甲基胂酸鐵)、氟苯嘧啶醇、辛噻酮、呋醯胺、肟醚菌胺、惡霜靈、氟噻唑吡乙酮(oxathiapiprolin)、㗁喹酸、㗁咪唑、氧化萎鏽靈、氧四環素、戊菌唑、戊菌隆、戊苯吡菌胺、吡噻菌胺、稻痕酯(perfurazoate)、亞磷酸(包括其鹽,如三乙膦酸鋁)、picarbutratox、啶氧菌酯、粉病靈、多氧黴素、噻菌靈、咪鮮胺、腐黴利、霜黴威、丙環唑、甲基代森鋅、丙氧喹啉、硫菌威、丙硫菌唑、唑菌胺酯、唑胺菌酯、唑菌酯、定菌磷、吡菌苯威、pyributacarb、啶斑肟、甲氧苯啶菌(pyriofenone)、perisoxazole、嘧黴胺、啶斑肟、吡咯尼群、咯喹酮、喹唑(quinconazole)、quinmethionate、喹氧靈、五氯硝基苯、矽噻菌胺、氟唑環菌胺、矽氟唑、螺環菌胺、鏈黴素、硫磺、戊唑醇、特弗喹啉(tebufloquin)、teclofthalam、克枯爛、四氧硝基苯、特比萘芬、氟醚唑、噻苯嗒唑、噻呋醯胺、托布津、甲基硫菌靈、福美雙、噻醯菌胺、甲基立枯磷、tolprocarb、甲苯氟磺胺、三唑酮、三唑醇、嘧菌醇、唑菌𠯤、三元硫酸銅、氯啶菌酯、十三𠰌啉、肟菌酯、氟菌唑、trimoprhamide三環唑、𠯤胺靈、滅菌唑、烯效唑、井岡黴素、霜黴滅(也被稱為valifenal)、乙烯菌核利、代森鋅、福美鋅和苯醯菌胺;殺線蟲劑諸如氟吡菌醯胺、螺蟲乙酯、硫雙威、噻唑膦、阿巴美丁、異菌脲、氟噻蟲碸(fluensulfone)、二甲基二硫醚、噻㗁唑碸、1,3-二氯丙烯(1,3-D)、威百畝(鈉和鉀)、棉隆、三氯硝基甲烷、苯線磷、丙線磷、硫線磷(cadusaphos)、特丁磷、新煙磷(imicyafos)、草胺醯、卡巴呋喃、噻㗁唑碸、堅強芽孢桿菌(Bacillus firmus )和巴斯德桿菌(Pasteuria nishizawae );殺細菌劑,諸如鏈黴素;殺蜱蟎亞綱動物劑,諸如雙甲脒、滅蟎猛、克氯苯、三環錫、三氯殺蟎醇、除蟎靈、乙蟎唑、喹蟎醚、苯丁錫、甲氰菊酯、唑蟎酯、噻蟎酮、克蟎特、嗒蟎靈和吡蟎胺。Additional examples of biologically active compounds or agents that can be formulated with the compounds of the present invention are: fungicides, such as aralic benzene-S-methyl, 4-dodecyl-2,6-dimethyl 𠰌line (Aldimorph), pyraclostrobin, azoxystrobin, dibendazim, penticonazole, azoxystrobin, benaxyl (including benaxyl), pyracyl, benendazim, benthiavalicarb (benthiavalicarb) (Including benthiavalicarb-isopropyl), benzovindiflupyr, 3-benzo[b]thiophen-2-yl-5,6-dihydro-1,4,2-thiol 𠯤 4-oxide (bethoxazin), bethoxazin, biphenyl, bifentriconazole, bixafen, blasticidin, flufenoxan, furoconazole, ethoxyfensulfonate, tributazone Special, chlorinate, cyprofen, dicaptan, captan, carbendazim, dimosan, chlorothalonil, acetocloride, copper hydroxide, copper oxychloride, copper sulfate, syringa Ester, Cyanofamid, Cyclofluranil, Cymoxanil, Cycloconazole, Cyprodinil, Diclofenac, Diclofenac, Tastrobin, Niclofenac, Dimethoprim, Difenconazole, Diflurin, methamphetamine, diflunomide, ketoxystrobin, diniconazole (including diniconazole-M), dimethopre, dithianon, dithiolane, dodecacycloline, doguo Dine, econazole, ethiconazole, difenfos, enoxastrobin (also known as enestroburin), epoxiconazole, ethaboxam, ethiconazole, terbendazole, pyraclostrobin, Fenpyridone, fenflunil, fenfluridol, mebendazole, metfuranil, fenpropanil, fenoxanil, seed dressing, fenpropidin, bufenoline, fenpyridone , Triphenyl tin acetate, triphenyl tin hydroxide, thiram, azoxystrobin, fluoxyquinoline, fluazinam, fludioxonil, fludioxon-methyl, fluorine, fluopyram, fluorine Pyraclostrobin, fluoxastrobin, fluquinazole, flusilazole, sulfonamide, flutianil (flutianil), flufenamide, fluconazole, fluconazole, fenconazole, tetrachlorobenzene Phthalin (also known as phthalide), Mai Suining, Furaxyl, Folabi, hexaconazole, hymexazol, biguanide, imazalil, amide azole, amide azole, alkane benzene sulfonate Standards, biguanide octamine triacetate, iodicarb, inoconazole, isothiazide (isofetamid), isorhafenac, iprodione, prosenzinc, orypyrin, pyrazoxane, isothiazide Amine, Kasugamycin, Keshouxin, Mancozeb, Mandestrobin, Mandestrobin, Mapanipyrin, Meprosamine, Acarina, Metalaxyl (including high-efficiency metalaxyl/fine nail cream Ling), metconazole, sulfondrocarb, disenbi, fenoxanil, fenoxanone, myclobutanil, naftitine, arsenic ferric ammonium (ferric methylarsonic acid), fluphenazine Alcohol, Octanthin, Furofuran, Orysastrobin, Oxathaline, Oxathiapiprolin (oxathiapiprolin), Oxolinic Acid, Omidazole, Oxyprosyl, Oxytetracycline, Penconazole, Penoxystrobin, penflufenamide, penthiopyramide, perfurazoate, phosphorous acid (including its salts, such as aluminum triethyl phosphonate), picarbutratox, picoxystrobin, powdery flu, polyoxo Promethycin, Thiabendazole, Prochloraz, Procymidone, Promabutacarb, Propiconazole, Zinc-Methylmethionate, Propoxyquin, Thiophanate, Prothioconazole, Pyraclostrobin, Zolamide Pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyributacarb, pyriofenone, pyriofenone, perisoxazole, pyrimethanil, pyrimethanone, pyrrolidin, pyrrolidone, quine (Quinconazole), quinmethionate, quinoxaline, pentachloronitrobenzene, siliclostrobin, flupyraclostrobin, silfluconazole, spiriconazole, streptomycin, sulfur, tebuconazole, tefquine Tebufloquin (tebufloquin), teclofthalam, gram rot, nitrobenzene, terbinafine, flufenoxazole, thiabendazole, thiafuramide, thiophanate, thiophanate-methyl, thiram, thiazolidine Triclosan, tolclofos-methyl, tolprocarb, tolflusulfonamide, triadimefon, triadimenol, azoxystrobin, pyraclostrobin, tribasic copper sulfate, chlorpyrifos, tridecaline, trifloxystrobin, Fluconazole, trimoprhamide, tricyclazole, tricyclazole, uniconazole, jinggangmycin, ponoxazole (also known as valifenal), vinclozolin, zinc thiazole, thiram and benzophenone Amine; nematicides such as fluopyram, spirotetramat, thiodicarb, thiazolyl, abamectin, iprodione, fluensulfone, dimethyl disulfide, thiodicarb Azole, 1,3-dichloropropene (1,3-D), methamphetamine (sodium and potassium), methenon, chloronitromethane, fenamiphos, promethphos, cadusaphos (cadusaphos) , Terbufos, imicyafos, imicyafos, carbofuran, thiazolidine, Bacillus firmus and Pasteuria nishizawae ; bactericides, such as streptomycin; Acaricidal agents, such as amitraz, fenprofen, crochlorobenzene, tricyclotin, dicofol, difenofen, etoxazole, fenazaquin, fenbutin, fenpropathrin, and pyraclosporin Ester, hexythiazox, cormite, tatafen, and pyraclostrobin.
在某些情況下,本發明化合物與其他生物學活性(特別是無脊椎有害生物防治)化合物或試劑(即,活性成分)之組合可導致大於累加(即,協同)的作用。降低釋放在環境中的活性成分的量,同時確保有效的有害生物防治一直是人們所希望的。當在施用率下發生無脊椎有害生物控制活性成分的協同作用,從而賦予農學上令人滿意的無脊椎有害生物控制水平時,此類組合可有利地用於降低作物生產成本並且減少環境負荷。In some cases, the combination of the compound of the present invention and other biologically active (especially invertebrate pest control) compounds or agents (ie, active ingredients) can result in more than additive (ie, synergistic) effects. It has always been desirable to reduce the amount of active ingredients released into the environment while ensuring effective pest control. When the synergistic effect of the invertebrate pest control active ingredients occurs at the application rate, thereby imparting an agronomically satisfactory level of invertebrate pest control, such a combination can be advantageously used to reduce crop production costs and reduce environmental load.
可以將本發明之化合物及其組成物施用至植物,該等植物經基因轉化以表現對無脊椎有害生物有毒的蛋白質(諸如蘇力菌δ-內毒素)。此種應用可以提供更廣譜的植物保護,並且對於抗性管理是有利的。外源施用的本發明化合物的效果可與所表現的毒素蛋白質協同作用。The compounds of the present invention and their compositions can be applied to plants, which have been genetically transformed to express proteins that are toxic to invertebrate pests (such as threnia δ-endotoxin). This application can provide a wider spectrum of plant protection and is beneficial for resistance management. The effect of the compound of the present invention administered exogenously can be synergistic with the expressed toxin protein.
該等農用保護劑(即殺昆蟲劑、殺真菌劑、殺線蟲劑、殺蜱蟎亞綱動物劑、除草劑和生物製劑)的一般參考文獻包括The Pesticide Manual [農藥手冊],第13版,C. D. S. Tomlin編輯,British Crop Protection Council [英國作物保護委員會],法納姆,薩里,英國,2003和The BioPesticide Manual [生物農藥手冊],第2版,L. G. Copping編輯,British Crop Protection Council [英國作物保護協會],法納姆,薩里,英國,2001。The general references for these agricultural protective agents (ie insecticides, fungicides, nematicides, acaricides, herbicides and biological agents) include The Pesticide Manual , 13th edition, Edited by CDS Tomlin, British Crop Protection Council [British Crop Protection Council], Farnham, Surrey, UK, 2003 and The BioPesticide Manual [Biological Pesticide Manual], 2nd edition, edited by LG Copping, British Crop Protection Council [British Crop Protection Council] Conservation Society], Farnham, Surrey, UK, 2001.
在農學和非農學應用中,藉由將生物學有效量之一種或多種通常呈組成物形式的本發明之化合物施用到有害生物環境中,包括侵害的農學和/或非農學所在地,施用到待保護的區域中,或直接施用到待控制的有害生物上,來控制寄生線蟲。In agronomic and non-agronomic applications, by applying a biologically effective amount of one or more of the compounds of the present invention, usually in the form of a composition, to the pest environment, including the agronomic and/or non-agronomic location of the infringement, applied to the target In the protected area, or directly applied to the pest to be controlled, to control parasitic nematodes.
因此,本發明包括一種用於在農學和/或非農業應用中控制寄生線蟲之方法,包括使寄生線蟲或其環境與生物學有效量之一種或多種本發明之化合物或與包含至少一種這樣的化合物的組成物或包含至少一種這樣的化合物和至少一種額外的生物學活性化合物或藥劑的組成物接觸。包含本發明之化合物和至少一種額外的生物學活性化合物或藥劑的合適組成物的實例包括顆粒狀組成物,其中該額外的活性化合物存在於與本發明之化合物相同的顆粒上或存在於與本發明之化合物的那些顆粒分開的顆粒上。Therefore, the present invention includes a method for controlling parasitic nematodes in agronomic and/or non-agricultural applications, comprising making the parasitic nematodes or their environment and biologically effective amounts of one or more compounds of the present invention or with at least one such A composition of compounds or a composition comprising at least one such compound and at least one additional biologically active compound or agent is contacted. Examples of suitable compositions comprising the compound of the present invention and at least one additional biologically active compound or medicament include granular compositions in which the additional active compound is present on the same particles as the compound of the present invention or is present in the same particle as the compound of the present invention. Those particles of the compound of the invention are separated from the particles.
為實現與本發明之化合物或組成物接觸以保護大田作物免受寄生線蟲的侵害,通常在種植之前將該化合物或組成物施用到作物種子上,施用到作物植物的葉子(例如,葉、莖、花、果實)上,或在種植作物之前或之後施用到土壤或其他生長培養基上。In order to achieve contact with the compound or composition of the present invention to protect field crops from parasitic nematodes, the compound or composition is usually applied to crop seeds and applied to the leaves (for example, leaves, stems, etc.) of the crop plants before planting. , Flowers, fruits), or applied to soil or other growth media before or after planting crops.
接觸方法的一個實施方式係藉由噴霧。可替代地,包含本發明之化合物的顆粒狀組成物可以施用到植物葉子上或土壤中。本發明之化合物也可以藉由使植物與作為液體配製物的土壤浸液、到土壤中的顆粒狀配製物、育苗箱處理物或移植浸泡物施用的包含本發明化合物之組成物相接觸藉由植物吸收有效地遞送。值得注意的是呈土壤浸液液體配製物形式的本發明之組成物。還值得注意的是一種用於控制寄生線蟲之方法,該方法包括使寄生線蟲或其環境與生物學有效量之本發明之化合物或與包含生物學有效量之本發明之化合物的組成物接觸。進一步值得注意的是這種方法,其中環境係土壤並且該組成物作為土壤浸液配製物施用到土壤中。另外值得注意的是還藉由局部施用到受侵害的所在地來使本發明之化合物係有效的。其他接觸方法包括藉由直接噴霧和滯留噴霧、空中噴霧、凝膠、種子包衣、微膠囊化、內吸吸收、餌料、耳標、大丸藥、噴霧器、熏劑、氣溶膠、粉劑以及許多其他方法來施用本發明之化合物或組成物。接觸方法的一個實施方式涉及包含本發明之化合物或組成物的尺寸上穩定的肥料顆粒、小棒或片劑。本發明之化合物還可浸漬到用於製造無脊椎有害生物控制裝置(例如,防昆蟲網)的材料中。One embodiment of the contact method is by spraying. Alternatively, the granular composition containing the compound of the present invention may be applied to plant leaves or soil. The compound of the present invention can also be obtained by contacting a plant with a composition containing the compound of the present invention applied as a liquid formulation of a soil infusion, a granular formulation into the soil, a nursery box treatment or a transplant infusion. Plant absorption and effective delivery. Of note is the composition of the invention in the form of a soil infusion liquid formulation. Also noteworthy is a method for controlling parasitic nematodes, which method comprises contacting the parasitic nematode or its environment with a biologically effective amount of a compound of the present invention or a composition containing a biologically effective amount of a compound of the present invention. Of further note is the method in which the environment is the soil and the composition is applied to the soil as a soil infusion formulation. It is also worth noting that the compounds of the present invention are effective by topical application to the affected area. Other contact methods include direct spray and retention spray, aerial spray, gel, seed coating, microencapsulation, systemic absorption, bait, ear tag, bolus, sprayer, fumigant, aerosol, powder and many others Method to administer the compound or composition of the present invention. One embodiment of the contact method involves dimensionally stable fertilizer granules, rods or tablets containing the compound or composition of the present invention. The compound of the present invention can also be impregnated into materials used to manufacture invertebrate pest control devices (for example, insect nets).
本發明之化合物還可用於種子處理劑中以保護種子免受寄生線蟲。在本揭露及申請專利範圍上下文中,處理種子意指使種子與典型地被配製成本發明之組成物的生物學有效量之本發明之化合物接觸。該種子處理劑保護種子免受無脊椎土壤有害生物並且總體上還可以保護由發芽種子發育成的幼苗的根和其他與土壤接觸的植株部位。該種子處理劑還可以藉由使本發明之化合物或第二活性成分在發育的植物中易位來向葉子提供保護。可將種子處理劑施用到所有類型的種子上,包括將發芽形成轉基因植物以表現特定性狀的那些。遺傳轉化植物的代表性實例包括表現對寄生線蟲有毒的蛋白質的那些,諸如蘇力菌毒素,或表現抗除草劑性的那些,諸如提供草甘膦抗性的草甘膦乙醯轉移酶。The compounds of the present invention can also be used in seed treatment agents to protect seeds from parasitic nematodes. In the context of the present disclosure and the scope of the patent application, treating the seed means contacting the seed with a biologically effective amount of the compound of the invention that is typically formulated as a composition of the invention. The seed treatment agent protects seeds from invertebrate soil harmful organisms and can also protect the roots of seedlings developed from germinated seeds and other plant parts in contact with the soil as a whole. The seed treatment agent can also provide protection to the leaves by translocating the compound of the present invention or the second active ingredient in the developing plant. Seed treatments can be applied to all types of seeds, including those that will germinate into transgenic plants to exhibit specific traits. Representative examples of genetically transformed plants include those that exhibit proteins toxic to parasitic nematodes, such as suridin toxin, or those that exhibit herbicide resistance, such as glyphosate acetotransferase that provides glyphosate resistance.
種子處理的一種方法係在播撒種子之前,藉由用本發明之化合物(即作為配製的組成物)對種子噴霧或撒粉。經配製用於種子處理的組成物一般包含成膜劑或黏合劑。因此,典型地,本發明之種子包衣組成物包含生物學有效量之式一 之化合物和成膜劑或黏合劑。可藉由將可流動的懸浮液濃縮物直接噴霧到種子的翻滾床中並且然後乾燥種子來為種子包衣。可替代地,可將其他配製物類型諸如濕粉、溶液、懸浮乳液、可乳化的濃縮物和水中的乳液噴霧在種子上。此方法對於將膜包衣施用在種子上係特別有用的。本領域技術者可採用各種包衣設備和方法。One method of seed treatment involves spraying or dusting the seeds with the compound of the present invention (that is, as a formulated composition) before sowing the seeds. Compositions formulated for seed treatment generally include film-forming agents or binders. Therefore, typically, the seed coating composition of the present invention contains a biologically effective amount of the compound of Formula 1 and a film-forming agent or a binder. Seeds can be coated by spraying the flowable suspension concentrate directly into a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types such as wet powders, solutions, suspension emulsions, emulsifiable concentrates, and emulsions in water can be sprayed on the seeds. This method is particularly useful for applying film coatings to seeds. Those skilled in the art can use various coating equipment and methods.
經處理的種子通常包含本發明之化合物,其量為從約0.1 g至1 kg/100 kg種子(即處理前按該種子的重量計從約0.0001%至1%)。經配製用於種子處理的可流動的懸浮液典型地包含從約0.5%至約70%的活性成分、從約0.5%至約30%的成膜黏合劑、從約0.5%至約20%的分散劑、從0%至約5%的增稠劑、從0%至約5%的顏料和/或染料、從0%至約2%的消泡劑、從0至約1%的防腐劑、以及從0%至約75%的揮發性液體稀釋劑。The treated seed usually contains the compound of the present invention in an amount of from about 0.1 g to 1 kg/100 kg of seed (ie, from about 0.0001% to 1% by weight of the seed before treatment). Flowable suspensions formulated for seed treatment typically contain from about 0.5% to about 70% active ingredient, from about 0.5% to about 30% film-forming binder, from about 0.5% to about 20% Dispersant, thickener from 0% to about 5%, pigment and/or dye from 0% to about 5%, defoamer from 0% to about 2%, preservative from 0 to about 1% , And from 0% to about 75% volatile liquid diluent.
對於農學應用,有效控制所需的施用率(即「生物學有效量」)將取決於諸如以下的因素:待控制的線蟲物種、線蟲的生命週期、生命階段、其大小、位置、一年中的時間、宿主作物或動物、取食行為、交配行為、環境濕度、溫度等。在正常情況下,每公頃約0.01至2 kg活性成分的施用率足以控制農學生態系統中的線蟲,但可能只需要0.0001 kg/公頃就足夠,或者可能需要多達8 kg/公頃。對於非農學用途,有效使用率範圍為約1.0 mg/平方米至50 mg/平方米,但可能只需0.1 mg/平方米就足夠,或者可能需要多達150 mg/平方米。本領域技術者可以容易地確定希望的寄生線蟲控制水平所需的生物學有效量。For agronomic applications, the application rate (ie, "biologically effective amount") required for effective control will depend on factors such as the nematode species to be controlled, the life cycle of the nematode, the life stage, its size, location, and the time of year Time, host crop or animal, feeding behavior, mating behavior, environmental humidity, temperature, etc. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control nematodes in agronomic ecosystems, but only 0.0001 kg/ha may be sufficient, or as much as 8 kg/ha may be required. For non-agricultural purposes, the effective utilization rate ranges from about 1.0 mg/m² to 50 mg/m², but only 0.1 mg/m² may be sufficient, or as much as 150 mg/m² may be required. Those skilled in the art can easily determine the biologically effective amount required for the desired level of parasitic nematode control.
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