CN112752753A - 包含吲唑化合物的杀虫混合物 - Google Patents
包含吲唑化合物的杀虫混合物 Download PDFInfo
- Publication number
- CN112752753A CN112752753A CN201980059629.4A CN201980059629A CN112752753A CN 112752753 A CN112752753 A CN 112752753A CN 201980059629 A CN201980059629 A CN 201980059629A CN 112752753 A CN112752753 A CN 112752753A
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- China
- Prior art keywords
- compound
- compounds
- aphid
- cyhalothrin
- cypermethrin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 181
- 230000000361 pesticidal effect Effects 0.000 title description 3
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 209
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 120
- 238000000034 method Methods 0.000 claims abstract description 59
- 229940125904 compound 1 Drugs 0.000 claims abstract description 39
- -1 fenaminoquinone Chemical compound 0.000 claims description 149
- 239000003085 diluting agent Substances 0.000 claims description 39
- 239000007788 liquid Substances 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 239000004094 surface-active agent Substances 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 26
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 20
- 239000005660 Abamectin Substances 0.000 claims description 18
- 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 16
- 239000005927 Pyriproxyfen Substances 0.000 claims description 16
- 229950008167 abamectin Drugs 0.000 claims description 16
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims description 16
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 claims description 15
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 14
- 229940097012 bacillus thuringiensis Drugs 0.000 claims description 14
- 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 14
- 241000894006 Bacteria Species 0.000 claims description 13
- 230000000967 entomopathogenic effect Effects 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 12
- 239000005926 Pyridalyl Substances 0.000 claims description 12
- 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 claims description 12
- 239000005663 Pyridaben Substances 0.000 claims description 11
- 241000700605 Viruses Species 0.000 claims description 11
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 claims description 11
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 11
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 10
- 239000005946 Cypermethrin Substances 0.000 claims description 10
- 239000005940 Thiacloprid Substances 0.000 claims description 10
- 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 10
- 229960005424 cypermethrin Drugs 0.000 claims description 10
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 239000002917 insecticide Substances 0.000 claims description 10
- 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 9
- 239000005889 Cyantraniliprole Substances 0.000 claims description 9
- 239000005897 Etoxazole Substances 0.000 claims description 9
- 239000005899 Fipronil Substances 0.000 claims description 9
- 239000005901 Flubendiamide Substances 0.000 claims description 9
- 239000005903 Gamma-cyhalothrin Substances 0.000 claims description 9
- 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 9
- 229960002587 amitraz Drugs 0.000 claims description 9
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 9
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 9
- 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 9
- 229940013764 fipronil Drugs 0.000 claims description 9
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 claims description 9
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 claims description 9
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 9
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 8
- 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 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 8
- 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 8
- 239000005875 Acetamiprid Substances 0.000 claims description 8
- 239000005878 Azadirachtin Substances 0.000 claims description 8
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 8
- 239000005874 Bifenthrin Substances 0.000 claims description 8
- 239000005885 Buprofezin Substances 0.000 claims description 8
- 239000005886 Chlorantraniliprole Substances 0.000 claims description 8
- 239000005888 Clothianidin Substances 0.000 claims description 8
- 239000005892 Deltamethrin Substances 0.000 claims description 8
- 239000005898 Fenoxycarb Substances 0.000 claims description 8
- 239000005906 Imidacloprid Substances 0.000 claims description 8
- 239000005907 Indoxacarb Substances 0.000 claims description 8
- 239000005912 Lufenuron Substances 0.000 claims description 8
- 239000005925 Pymetrozine Substances 0.000 claims description 8
- 239000005934 Sulfoxaflor Substances 0.000 claims description 8
- 239000005937 Tebufenozide Substances 0.000 claims description 8
- 239000005941 Thiamethoxam Substances 0.000 claims description 8
- 239000005942 Triflumuron Substances 0.000 claims description 8
- 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 8
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 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 8
- 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 8
- 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 8
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims description 8
- 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 8
- 229960002483 decamethrin Drugs 0.000 claims description 8
- 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 8
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 claims description 8
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 8
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 8
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 claims description 8
- 229940056881 imidacloprid Drugs 0.000 claims description 8
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 8
- 229960000521 lufenuron Drugs 0.000 claims description 8
- 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 8
- 229940079888 nitenpyram Drugs 0.000 claims description 8
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 8
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims description 8
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 8
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 8
- 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 8
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 7
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 claims description 7
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- 229960001591 cyfluthrin Drugs 0.000 claims description 7
- 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 7
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims description 7
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 claims description 7
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 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
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 7
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims description 6
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005891 Cyromazine Substances 0.000 claims description 6
- 239000005894 Emamectin Substances 0.000 claims description 6
- 239000005895 Esfenvalerate Substances 0.000 claims description 6
- 239000005783 Fluopyram Substances 0.000 claims description 6
- 239000005787 Flutriafol Substances 0.000 claims description 6
- 239000005916 Methomyl 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
- 239000005664 Spirodiclofen Substances 0.000 claims description 6
- 239000005665 Spiromesifen Substances 0.000 claims description 6
- 239000005939 Tefluthrin Substances 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
相关申请的交叉引用
本申请要求享有2018年7月14日提交的美国临时申请No.62/698,035和2018年12月13日提交的美国临时申请No.62/778,992的权益。
技术领域
本发明涉及适用于农业和非农业用途的某些取代的吲唑、其组合物,以及其用于在农业和非农业环境中防治无脊椎害虫如节肢动物的方法。
背景技术
防治无脊椎害虫在实现高作物效率中是极其重要的。无脊椎害虫对生长和储存的农作物的损害可引起生产力的显著降低,并由此导致消费者的成本增加。对林业、温室作物、观赏植物、苗圃作物、储存食品和纤维产品、家畜、家庭、草皮、木质产品以及公共和动物健康中的无脊椎害虫的防治也是重要的。为了这些目的,许多产品是可商购的,但持续需要更有效、较低成本、较低毒性、对环境更安全或具有不同的作用位点的新型化合物。PCT申请公开WO 2015/038503A1公开了相关的吲唑化合物。
发明内容
本发明涉及化合物1或式2的化合物、包含它们的组合物及其用于防治无脊椎动物害虫的用途:
其中n为0、1或2。
本发明还提供包含化合物1或式2的化合物、或任何前述化合物的组合的组合物。
本发明还提供组合物,所述组合物包含化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分。在一个实施方案中,本发明还提供用于防治无脊椎害虫的组合物,所述组合物包含化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂。
本发明提供用于防治无脊椎害虫的方法,所述方法包括使所述无脊椎害虫或其环境与生物学有效量的化合物1或式2的化合物(例如,作为本文所述的组合物)接触。本发明还涉及这样的方法,其中使所述无脊椎害虫或其环境与包含生物学有效量的化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分的组合物接触,所述组合物任选地还包含生物学有效量的至少一种附加的生物学活性化合物或生物学活性剂。
本发明还提供用于保护种子免受无脊椎害虫侵害的方法,所述方法包括使所述种子与生物学有效量的化合物1或式2的化合物(例如,作为本文所述的组合物)接触。本发明还涉及经处理的种子。
发明详述
如本文所用,术语“包含(comprises,comprising)”、“包括(includes,including)”、“具有(has,having)”、“含有(contains,containing)”、“特征在于”或其任何其他变型旨在覆盖非排他性的包括,以任何明确指明的限定为条件。例如,包含一系列元素的组合物、混合物、工艺或方法不必仅限于那些元素,而是可以包括其他未明确列出的元素,或这样的组合物、混合物、工艺或方法固有的元素。
连接短语“由...组成”排除任何未指出的元素、步骤或成分。如果在权利要求中,则这样的短语会使权利要求为封闭式,使其不包含除那些描述的材料以外的材料,但通常与其相关的杂质除外。当短语“由...组成”出现在权利要求的主体的子句中,而非紧接前序部分时,其仅限制在该子句中提到的元素;其他元素不作为整体从权利要求中被排除。
连接短语“基本上由...组成”用于限定除了字面披露的那些以外还包括材料、步骤、特征、组分或元素的组合物或方法,条件是这些附加的材料、步骤、特征、组分或元素不会实质影响请求保护的发明的基本和新颖特征。术语“基本上由...组成”居于“包含”和“由...组成”中间。
当申请人已经用开放式术语如“包含”定义了发明或其一部分时,则应易于理解(除非另外指明),说明书应被解释为还使用术语“基本上由...组成”或“由...组成”描述这样的发明。
此外,除非有相反的明确说明,“或”是指包含性的“或”,而不是指排他性的“或”。例如,条件A或B由下列任一项满足:A是真(或存在)和B是假(或不存在),A是假(或不存在)和B是真(或存在),和A和B二者都是真(或存在)。
同样,在本发明的元素或组分前的英文不定冠词“a”和“an”对于所述元素或组分的例子(即,出现)的数目旨在是非限制性的。因此,“一个/一种”应理解为包括一个/一种或至少一个/一种,并且元素或组分的单数词语形式还包括复数,除非该数值明显意指单数。
如本公开所提及,术语“无脊椎害虫”包括作为害虫具有经济重要性的节肢动物、腹足动物、线虫和蠕虫。术语“节肢动物”包括昆虫、螨虫、蜘蛛、蝎子、蜈蚣、千足虫、球潮虫和综合纲(symphylan)。术语“腹足动物”包括蜗牛、蛞蝓和其他柄眼亚目。术语“线虫”包括线虫动物门的成员,例如植食性的线虫和寄生于动物的蠕虫线虫。术语“蠕虫”包括所有的寄生虫,如蛔虫(线虫动物门)、犬恶丝虫(线虫动物门,胞管肾纲类)、吸虫(扁形动物门,吸虫纲)、棘头虫(棘头动物门)和绦虫(扁形动物门,绦虫纲)。
在本公开的上下文中,“无脊椎害虫防治”是指抑制无脊椎害虫发育(包括死亡率、取食减少和/或交配干扰),并且相关的表达以类似方式定义。
术语“农业”是指大田作物的生产,例如用于食物和纤维,并且包括玉蜀黍或玉米、大豆和其他豆类、稻、谷类(例如,小麦、燕麦、大麦、黑麦和稻)、叶类蔬菜(例如,莴苣、卷心菜和其他甘蓝类作物)、水果蔬菜(例如,西红柿、胡椒、茄子、十字花科植物和葫芦)、马铃薯、甘薯、葡萄、棉花、木本果(例如,梨果、核果(stone)和柑橘)、小果(例如,浆果和樱桃)和其他特种作物(例如,低芥酸菜籽、向日葵和橄榄)的生长。
术语“非农业”是指不同于大田作物,如园艺作物(例如,不在田地生长的温室、苗圃或观赏植物)、住宅、农业、商业和工业结构,草皮(例如,草场、牧场、高尔夫球场、草坪、运动场等)、木制产品、储存产品、农业林业和植被管理、公共卫生(即人类)和动物健康(例如,驯养动物如宠物、家畜和家禽,非驯养动物如野生动物)应用。
术语“作物活力”是指作物植物的生长速率或生物质积累。“活力的增加”是指作物植物相对于未处理的对照作物植物在生长或生物质积累上的增加。术语“作物产率”是指收获作物植物后获得的作物材料的在数量和质量二者上的回报。“作物产率的增加”是指相对于未处理的对照作物植物的作物产率增加。
术语“生物学有效量”是指当施用于(即接触)待防治的无脊椎害虫或其环境,或植物、生长植物的种子或植物的所在地(例如,生长介质)以保护植物免受无脊椎害虫的伤害或为了其他所期望的效果(例如,增加植物活力)时足以产生所期望生物效应的生物学活性化合物(例如,化合物1或式2的化合物)的量。
本发明的如在发明内容中所述的实施方案包括下述的那些。
实施方案1.化合物1。
实施方案2.式2的化合物,其中n为0、1或2。
实施方案3.式2的化合物,其中n为0。
实施方案4.式2的化合物,其中n为1。
实施方案5.式2的化合物,其中n为2。
实施方案6.化合物,其中所述化合物是选自以下中的之一:
N-[1-(二氟甲基)环丙基]-2-(3-吡啶基)-2H-吲唑-4-甲酰胺;N-[1,1-二甲基-2-(甲硫基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺;N-[1,1-二甲基-2-(甲基亚磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺;和N-[1,1-二甲基-2-(甲基磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺;或任何上述化合物的组合。
实施方案7.组合物,所述组合物包含化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂。
实施方案8.组合物,所述组合物包含化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂,其中所述至少一种附加的生物学活性化合物或生物学活性剂选自:阿巴美丁、高灭磷、灭螨醌、啶虫脒、氟丙菊酯、啶喃环丙虫酯、磺胺螨酯、双甲脒、阿维菌素、印楝素、谷硫磷、丙硫克百威、杀虫磺、联苯菊酯、联苯肼酯、双三氟虫脲、硼酸盐、噻嗪酮、西维因、卡巴呋喃、杀螟丹、伐虫脒、氯虫苯甲酰胺、溴虫腈、定虫隆、毒死蜱、甲基毒死蜱、环虫酰肼、螨死净、噻虫胺、氰虫酰胺、环溴虫酰胺、乙氰菊酯、环氧虫啶、丁氟螨酯、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、灭蝇胺、溴氰菊酯、丁醚脲、二嗪农、狄氏剂、二氟脲、四氟甲醚菊酯、杀虫双、乐果、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、苯丁锡、杀螟硫磷、苯硫威、苯氧威、甲氰菊酯、氰戊菊酯、氟虫腈、flometoquin、氟啶虫酰胺、氟虫酰胺、氟氰戊菊酯、嘧虫胺、氟虫脲、氟菌螨酯、氟噻虫砜、氟吡菌酰胺、flupiprole、氟吡呋喃酮、氟胺氰菊酯、τ-氟胺氰菊酯、地虫硫磷、伐虫脒、噻唑磷、氯虫酰肼、heptafluthrin、氟铃脲、噻螨酮、氟蚁腙、吡虫啉、茚虫威、杀虫皂、异柳磷、虱螨脲、马拉硫磷、氯氟醚菊酯、氰氟虫腙、蜗牛敌、甲胺磷、杀扑磷、甲硫双威、灭多虫、甲氧普林、甲氧滴滴涕、甲氧苄氟菊酯、久效磷、monofluthrin、甲氧虫酰肼、烯啶虫胺、硝乙脲噻唑、双苯氟脲、多氟脲、草氨酰、对硫磷、甲基对硫磷、扑灭司林、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯、克螨特、丙苯烃菊酯、pyflubumide、吡蚜酮、吡嗪氟虫腈、除虫菊酯、哒螨灵、啶虫丙醚、新喹唑啉(间二氮杂苯)类杀虫剂、嘧螨胺、吡啶氟虫腈、蚊蝇醚、鱼藤酮、利阿诺定、氟硅菊酯、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、硫丙磷、砜虫啶、虫酰肼、吡螨胺、伏虫脲、七氟菊酯、特丁磷、杀虫畏、似虫菊、四氟醚菊酯、噻虫啉、噻虫嗪、硫双威、杀虫双、唑虫酰胺、四溴菊酯、唑蚜威、敌百虫、杀铃脲、苏云金芽孢杆菌(Bacillus thuringiensis)的所有菌株、昆虫病原细菌、核型多角体(Nucleopolyhedrosis)病毒的所有毒株、昆虫病原病毒以及昆虫病原真菌。
实施方案9.组合物,所述组合物包含化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂,其中所述至少一种附加的生物学活性化合物或生物学活性剂选自:阿巴美丁、啶虫脒、氟丙菊酯、啶喃环丙虫酯、双甲脒、阿维菌素、印楝素、丙硫克百威、杀虫磺、联苯菊酯、3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-1H-吡唑-5-甲酰胺、噻嗪酮、西维因、杀螟丹、氯虫苯甲酰胺、溴虫腈、毒死蜱、噻虫胺、氰虫酰胺、环溴虫酰胺、乙氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、λ-三氟氯氰菊酯、γ-三氟氯氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、灭蝇胺、溴氰菊酯、狄氏剂、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、杀螟硫磷、苯硫威、苯氧威、氰戊菊酯、氟虫腈、flometoquin、氟啶虫酰胺、氟虫酰胺、氟虫脲、氟菌螨酯、氟噻虫砜、flupiprole、氟吡呋喃酮、氟胺氰菊酯、伐虫脒、噻唑磷、heptafluthrin、氟铃脲、氟蚁腙、吡虫啉、茚虫威、虱螨脲、氯氟醚菊酯、氰氟虫腙、甲硫双威、灭多虫、甲氧普林、甲氧虫酰肼、甲氧苄氟菊酯、monofluthrin、烯啶虫胺、硝乙脲噻唑、双苯氟脲、草氨酰、pyflubumide、吡蚜酮、除虫菊酯、哒螨灵、啶虫丙醚、嘧螨胺、蚊蝇醚、利阿诺定、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、砜虫啶、虫酰肼、似虫菊、噻虫啉、噻虫嗪、硫双威、杀虫双、四溴菊酯、四氟醚菊酯、唑蚜威、杀铃脲、苏云金芽孢杆菌的所有菌株以及核型多角体病毒的所有毒株。
实施方案10.用于防治无脊椎害虫的方法,所述方法包括使所述无脊椎害虫或其环境与生物学有效量的化合物1或式2的化合物接触。
实施方案11.经处理的种子,所述经处理的种子包含按所述种子在处理之前的重量计约0.0001%至1%的量的化合物1或式2的化合物。
值得注意的是,本发明的化合物的特征在于有利的代谢和/或土壤残留模式,并表现出防治广谱的农业和非农业无脊椎害虫的活性。
特别值得注意的是,由于无脊椎害虫防治谱和经济重要性的原因,通过防治无脊椎害虫保护农作物免受由无脊椎害虫引起的损害或伤害是本发明的实施方案。本发明的化合物由于其在植物中的有利的易位特性或内吸性还保护叶或不与化合物1或式2的化合物或包含所述化合物的组合物直接接触的其他植物部分。
还值得注意的作为本发明的实施方案的是这样的组合物,所述组合物包含前述实施方案中任一者以及本文所述的任何其他实施方案的化合物及其任何组合,以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂。
另外值得注意的作为本发明的实施方案的是用于防治无脊椎害虫的组合物,所述组合物包含前述实施方案中任一者以及本文所述的任何其他实施方案的化合物及其任何组合,以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂。本发明的实施方案还包括用于防治无脊椎害虫的方法,所述方法包括使所述无脊椎害虫或其环境与生物学有效量的如前述实施方案中任一者所述的化合物(例如,作为本文所述的组合物)接触。
本发明的实施方案还包括呈土壤浸液液体制剂形式的组合物,所述组合物包含如前述实施方案中任一者所述的化合物。本发明的实施方案还包括用于防治无脊椎害虫的方法,所述方法包括使土壤与作为土壤浸液的液体组合物接触,所述土壤浸液包含生物学有效量的如前述实施方案中任一者所述的化合物。
本发明的实施方案还包括用于防治无脊椎害虫的喷雾组合物,所述喷雾组合物包含生物学有效量的如前述实施方案中任一者所述的化合物和抛射剂。本发明的实施方案还包括用于防治无脊椎害虫的诱饵组合物,所述诱饵组合物包含生物学有效量的如前述实施方案中任一者所述的化合物、一种或多种食物材料、任选存在的引诱剂和任选存在的湿润剂。本发明的实施方案还包括用于防治无脊椎害虫的装置,所述装置包括所述诱饵组合物和适于容纳所述诱饵组合物的壳体,其中所述壳体具有至少一个开口,所述开口的尺寸允许所述无脊椎害虫通过所述开口,使得所述无脊椎害虫可以从所述壳体外部的位置接近所述诱饵组合物,并且其中所述壳体还适于放置在所述无脊椎害虫的潜在或已知活动场所中或附近。
本发明的实施方案还包括用于保护种子免受无脊椎害虫侵害的方法,所述方法包括使所述种子与生物学有效量的如前述实施方案中任一者所述的化合物接触。
本发明的实施方案还包括用于保护动物免受无脊椎寄生害虫侵害的方法,所述方法包括向所述动物施用杀寄生虫有效量的如前述实施方案中任一者所述的化合物。
本发明的实施方案还包括用于防治无脊椎害虫的方法,所述方法包括使所述无脊椎害虫或其环境与生物学有效量的化合物1或式2的化合物(例如,作为本文所述的组合物)接触,条件是所述方法不是通过疗法对人或动物体进行医学治疗的方法。
本发明还涉及这样的方法,其中所述该无脊椎害虫或其环境与包含生物学有效量的化合物1或式2的化合物以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分的组合物接触,所述组合物任选地还包含生物学有效量的至少一种附加的生物学活性化合物或生物学活性剂,条件是所述方法不是通过疗法对人或动物体进行医学治疗的方法。
化合物1或式2的化合物可通过路线1和2所述的以下方法和变体来制备。使用以下缩写:DMF为N,N-二甲基甲酰胺,DCC为N,N'-二环己基碳二亚胺,HATU为1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸盐。
化合物1可以通过路线1中所示的方法由化合物3制备。在该方法中,在酰胺偶联剂诸如DCC或HATU的存在下,通过化合物3的羧基与化合物4的胺基的酰胺键形成反应来制备化合物1。对于代表性的试剂和反应条件,参见Jones,J.The Chemical Synthesis ofPeptides,International Series of Monographs on Chemistry,Oxford University:Oxford,1994。
路线1
化合物3(CAS登记号2001277-98-9)在本领域中是已知的。
式2(其中n为0)的化合物(化合物2a)可以通过路线2所示的方法由化合物5制备。路线2的方法类似于路线1中关于化合物1的制备所描述的方法。在该方法中,在酰胺偶联剂诸如DCC或HATU的存在下,通过化合物5的羧基与化合物6的胺基的酰胺键形成反应来制备化合物2。
路线2
式2(其中n为1或2)的化合物(即,分别为亚砜2b或砜2c)可以通过硫化物2a的氧化来制备。用于将硫化物氧化为亚砜和砜的多种方法和试剂是本领域已知的。这种氧化剂的实例包括间氯过氧苯甲酸和高碘酸钠。
应认识到,上述用于制备化合物1或式2的化合物的某些试剂和反应条件可能不与中间体中存在的某些官能团相容。在这些情况下,将保护/脱保护序列或官能团互变引入到合成中将有助于获得所期望的产物。保护基的使用和选择对于化学合成领域的技术人员而言会是显而易见的(参见例如Greene,T.W.、Wuts,P.G.M.Protective Groups in OrganicSynthesis,第2版;Wiley:New York,1991)。本领域技术人员会认识到,在一些情况下,在引入任何单独路线中的描述的试剂后,可能需要实施未详细描述的额外常规合成步骤,以完成化合物1或式2的化合物的合成。本领域技术人员还会认识到,可能需要以与制备化合物1或式2的化合物时呈现的具体顺序不同的顺序来实施上文路线中示出的步骤的组合。
本领域技术人员还会认识到,本文所述的化合物1或式2的化合物和中间体可经历各种亲电反应、亲核反应、自由基反应、有机金属反应、氧化反应和还原反应,以引入取代基或修饰现有的取代基。
无需进一步详尽说明,相信本领域技术人员使用以上所述内容可将本发明利用至最大限度。因此,以下合成例应理解为仅是例证性的,而不以任何方式限制本发明的公开内容。以下合成例中的步骤示出了整个合成转化中每个步骤的操作,并且用于每个步骤的原料不必由在其他实施例或步骤中描述了操作的具体制备步骤制得。百分比均按重量计,除非是色谱溶剂混合物或除非另外指明。色谱溶剂混合物的份数和百分比均按体积计,除非另外指明。以距四甲基硅烷的低场ppm数为单位报告1H NMR波谱;“s”表示单峰,“d”表示双峰,“t”表示三峰,“q”表示四峰,“m”表示多峰,“dd”表示双重双峰,“dt”表示双重三峰,“brs”表示宽单峰。DMF表示N,N-二甲基甲酰胺。化合物编号参见索引表A。
合成例1
N-[1-(二氟甲基)环丙基]-2-(3-吡啶基)-2H-吲唑-4-甲酰胺(化合物1)的制备
步骤A:N-[1-(二氟甲基)环丙基]-2-(3-吡啶基)-2H-吲唑-4-甲酰胺的制备
将2-(3-吡啶基)-2H-吲唑-4-羧酸(100mg,0.42mmol,CAS登记号2001277-98-9)、HATU(190mg,0.5mmol)、1-(二氟甲基)环丙胺盐酸盐(71mg,0.5mmol)在DMF(2mL)中的溶液用三乙胺(174pL,1.25mmol)处理。将反应混合物在室温下搅拌过夜。然后将反应混合物通过反相柱色谱法直接纯化[用10%-100%MeCN/MeOH(1∶1):水洗脱C18柱],得到标题化合物,即本发明的化合物(105mg,76%收率)。1H NMR(500MHz,DMSO-d6)δppm 9.35-9.39(m,2H)9.14(s,1H)8.67-8.68(m,1H)8.55-8.58(m,1H)7.94-7.97(m,1H),7.73-7.75(m,1H),7.63-7.67(m,1H),7.41-7.45(m,1H),6.21(t,1H),1.13-1.17(m,2H),1.02-1.06(m,2H)。
合成例2
N-[1,1-二甲基-2-(甲硫基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺(化合物2a)的制备
步骤A:N-[1,1-二甲基-2-(甲硫基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺(化合物2a)的制备
将7-氟-2-(3-吡啶基)-2H-吲唑-4-羧酸(10g,39mmol)、HATU(17.7g,47mmol)、2-甲基-1-甲基硫烷基-丙-2-胺(7g,58mmol)在DMF(100mL)中的溶液用三乙胺(16mL,117mmol)处理。将反应混合物在室温下搅拌4小时。将反应混合物用EtOAc(300mL)稀释,并用水(6×100mL)洗涤。分离有机层并真空浓缩。所得粗固体通过正相色谱法纯化(用70-100%EtOAc的己烷溶液洗脱硅胶),得到标题化合物,即本发明的化合物(9.9g,71%收率)。1HNMR(500MHz,DMSO-d6)δppm 9.37-9.43(m,2H),8.69-8.72(m,1H),8.56-8.60(m,1H),8.00(s,1H),7.64-7.70(m,2H),7.22-7.27(m,1H),3.11(s,2H),2.09(s,3H),1.47(s,6H)。
化合物2b(N-[1,1-二甲基-2-(甲基亚磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H吲唑-4-甲酰胺)和化合物2c(N-[1,1-二甲基-2-(甲基磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H吲唑-4-甲酰胺各自可以通过化合物2a的氧化来制备。
本发明的化合物一般用作组合物(即制剂)中的无脊椎害虫防治活性成分,所述组合物含有至少一种用作载体的附加组分,所述附加组分选自表面活性剂、固体稀释剂和液体稀释剂。选择所述制剂或组合物成分,以与所述活性成分的物理特性、施用方式和环境因素(如土壤类型、湿度和温度)一致。
有用的制剂包括液体和固体组合物。液体组合物包括溶液剂(包括乳油(emulsifiable concentrate))、混悬剂、乳剂(包括微乳剂、水包油乳剂、可流动浓缩物(flowable concentrate)和/或悬乳剂(suspoemulsion))等,它们可以任选地被稠化成凝胶。水性液体组合物的一般类型为可溶性浓缩物、悬浮浓缩物、胶囊混悬剂、浓缩乳剂、微乳剂、水包油悬乳剂、可流动浓缩物和悬乳剂。非水性液体组合物的一般类型为乳油、可微乳化的浓缩物、可分散浓缩物和油分散体。
固体组合物的一般类型为粉剂(dust)、粉末(powder)、颗粒剂、粒料(pellet)、小球(prill)、锭剂、片剂、填充膜(包括种子包衣)等,它们可以是水分散性的(“可润湿的”)或水溶性的。由成膜溶液剂或可流动混悬剂形成的膜和包衣尤其可用于种子处理。活性成分可被(微)胶囊包封,并且进一步形成混悬剂或固体制剂;或者,可将含有活性成分的整个制剂包囊(或“包覆”)。包囊可以控制或延迟活性成分的释放。可乳化的颗粒结合了乳油制剂和干颗粒制剂两者的优点。高强度组合物主要用作用于进一步配制的中间体。
可喷洒制剂通常在喷洒之前分散在合适的介质中。将此类液体和固体制剂配制成易于在喷洒介质(通常是水,但偶尔也可以是其他适合的介质,例如芳烃或石蜡烃或植物油)中稀释。喷洒量的范围可以为每公顷约一升至数千升,更通常为每公顷约十升至数百升。可将可喷洒制剂在水槽中与水或另一种合适的介质混合,用于通过空气或地面施用处理叶片,或者施用到植物的生长介质中。液体制剂和干制剂可以直接定量加入到滴灌系统中,或者在栽培期间定量加入到垄沟中。液体制剂和固体制剂可以在种植之前的种子处理时施用于作物和其他期望的植物的种子上,以便通过全身吸收来保护发育中的根和其他地面下的植物部分和/或叶。
所述制剂通常包含有效量的活性成分、稀释剂和表面活性剂,其在如下的大概的范围内,总和为按重量计100%。
重量百分比
固体稀释剂包括例如粘土(例如膨润土、蒙脱石、绿坡缕石和高岭土)、石膏、纤维素、二氧化钛、氧化锌、淀粉、糊精、糖(例如乳糖、蔗糖)、二氧化硅、滑石、云母、硅藻土、尿素、碳酸钙、碳酸钠和碳酸氢钠、以及硫酸钠。通常的固体稀释剂描述于Watkins等人的Handbook of Insecticide Dust Diluents and Carriers,第2版(Dorland Books,Caldwell,New Jersey)中。
液体稀释剂包括例如水、N,N-二甲基烷酰胺(例如N,N-二甲基甲酰胺)、柠檬烯、二甲基亚砜、N-烷基吡咯烷酮(例如N-甲基吡咯烷酮)、烷基磷酸酯(例如磷酸三乙酯)、乙二醇、三甘醇、丙二醇、二丙二醇、聚丙二醇、碳酸亚丙酯、碳酸亚丁酯、石蜡(例如石腊油、正链烷烃、异链烷烃)、烷基苯、烷基萘、甘油、三乙酸甘油酯、山梨醇、芳族烃、脱芳构化脂族化合物、烷基苯、烷基萘、酮(诸如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮)、乙酸酯(诸如乙酸异戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酯、乙酸十三烷酯和乙酸异冰片酯)、其他酯(诸如烷基化的乳酸酯、二价苯甲酸烷基酯和苯甲酸芳基酯、γ-丁内酯)、以及可以是直链、支链、饱和或不饱和的醇(诸如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、正己醇、2-乙基己醇、正辛醇、癸醇、异癸醇、异十八醇、鲸蜡醇、月桂醇、十三烷醇、油醇、环己醇、四氢糠醇、二丙酮醇、甲酚和苄醇。液体稀释剂还包括饱和的和不饱和脂肪酸(通常为C6-C22)的甘油酯,如植物种子和果实的油(例如橄榄油、蓖麻油、亚麻籽油、芝麻油、玉米油、花生油、葵花籽油、葡萄籽油、红花油、棉籽油、大豆油、油菜籽油、椰子油和棕榈仁油)、动物源脂肪(例如牛脂、猪脂、猪油、鳕鱼肝油、鱼油)、以及它们的混合物。液体稀释剂还包括烷基化(例如甲基化、乙基化、丁基化)的脂肪酸,其中脂肪酸可以通过源自植物和动物的甘油酯的水解获得,并且可通过蒸馏进行纯化。通常的液体稀释剂描述于Marsden的SolventsGuide,第2版(Interscience,New York,1950)中。
本发明的固体和液体组合物通常包含一种或多种表面活性剂。当加进液体中时,表面活性剂(还被称为“表面活性试剂”)通常改变,最通常降低液体的表面张力。根据表面活性剂分子中的亲水基团和亲脂基团的性质,表面活性剂可用作润湿剂、分散剂、乳化剂或消泡剂。
表面活性剂可分为非离子、阴离子或阳离子表面活性剂。可用于本发明的组合物的非离子表面活性剂包括但不限于:醇烷氧基化物,诸如基于天然醇和合成醇(其可以是支链或直链的)并且由醇和环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制得的醇烷氧基化物;胺乙氧基化物、链烷醇酰胺和乙氧基化链烷醇酰胺;烷氧基化甘油三酯,诸如乙氧基化的大豆油、蓖麻油和油菜籽油;烷基苯酚烷氧基化物,诸如辛基苯酚乙氧基化物、壬基苯酚乙氧基化物、二壬基苯酚乙氧基化物和十二烷基苯酚乙氧基化物(由苯酚和环氧乙烷、环氧丙烷、环氧丁烷或它们混合物制得);由环氧乙烷或环氧丙烷制得的嵌段聚合物,和其中末端嵌段由环氧丙烷制得的反式嵌段聚合物;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苯酚(包括由环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制得的那些);脂肪酸酯、甘油酯、羊毛脂系衍生物、多乙氧基化酯(诸如多乙氧基化脱水山梨糖醇脂肪酸酯、多乙氧基化山梨醇脂肪酸酯和多乙氧基化甘油脂肪酸酯);其他脱水山梨糖醇衍生物,诸如脱水山梨糖醇酯;聚合物表面活性剂,诸如无规共聚物、嵌段共聚物、醇酸peg(聚乙二醇)树脂、接枝或梳型聚合物以及星型聚合物;聚乙二醇(peg);聚乙二醇脂肪酸酯;硅氧烷系表面活性剂;和糖衍生物,诸如蔗糖酯、烷基多苷和烷基多糖。
有用的阴离子表面活性剂包括但不限于:烷基芳基磺酸及其盐;羧化醇或烷基苯酚乙氧基化物;二苯基磺酸酯衍生物;木质素和木质素衍生物,诸如木质素磺酸盐;马来酸或琥珀酸或它们的酸酐;烯烃磺酸酯;磷酸酯,诸如醇烷氧基化物的磷酸酯、烷基苯酚烷氧基化物的磷酸酯、和苯乙烯基苯酚乙氧基化物的磷酸酯;蛋白质系表面活性剂;肌氨酸衍生物;苯乙烯基苯酚醚硫酸盐;油和脂肪酸的硫酸盐和磺酸盐;乙氧基化烷基苯酚的硫酸盐和磺酸盐;醇的硫酸盐;乙氧基化醇的硫酸盐;胺和酰胺的磺酸盐,诸如N,N-烷基牛磺酸盐;苯、枯烯、甲苯、二甲苯以及十二烷基苯和十三烷基苯的磺酸盐;缩聚萘的磺酸盐;萘和烷基萘的磺酸盐;石油馏分的磺酸盐;磺基琥珀酰胺酸盐(sulfosuccinamate);以及磺基琥珀酸盐和它们的衍生物,诸如二烷基磺基琥珀酸盐。
有用的阳离子表面活性剂包括但不限于:酰胺和乙氧基化酰胺;胺诸如N-烷基丙二胺、三亚丙基三胺和二亚丙基四胺,和乙氧基化胺、乙氧基化二胺以及丙氧基化胺(由胺和环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物制得);胺盐诸如胺乙酸盐,和二胺盐;季铵盐,诸如季盐、乙氧基化季盐和二季盐;以及胺氧化物,诸如烷基二甲基胺氧化物和二-(2-羟基乙基)-烷基胺氧化物。
还可用于本发明的组合物的是非离子表面活性剂和阴离子表面活性剂的混合物,或非离子表面活性剂和阳离子表面活性剂的混合物。非离子、阴离子和阳离子表面活性剂及其推荐应用公开于多种已公布的参考文献中,包括由McCutcheon’s Division,TheManufacturing Confectioner Publishing Co.出版的McCutcheon’s Emulsifiers andDetergents(北美和国际年鉴版);Sisely和Wood的Encyclopedia of Surface ActiveAgents(Chemical Publ.Co.,Inc.,New York,1964);以及A.S.Davidson和B.Milwidsky的Synthetic Detergents,第七版(John Wiley and Sons,New York,1987)。
本发明的组合物还可包含本领域技术人员已知为制剂助剂的制剂助剂和添加剂(其中一些也可被认为是起到固体稀释剂、液体稀释剂或表面活性剂的作用)。此类制剂助剂和添加剂可控制:pH(缓冲剂)、加工过程中的起泡(消泡剂,如聚有机硅氧烷)、活性成分的沉降(助悬剂)、粘度(触变增稠剂)、容器内的微生物生长(抗微生物剂)、产品冷冻(防冻剂)、颜色(染料/颜料分散体)、洗脱(成膜剂或粘合剂)、蒸发(防蒸发剂),以及其他制剂属性。成膜剂包括例如聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯烷酮-乙酸乙烯酯共聚物、聚乙烯醇、聚乙烯醇共聚物和蜡。制剂助剂和添加剂的实例包括由McCutcheon’sDivision,The Manufacturing Confectioner Publishing Co.出版的McCutcheon’sVolune 2:Functional Materials(北美和国际年鉴版);和PCT公布WO03/024222中所列的那些。
通常通过将活性成分溶于溶剂中或通过在液体或干稀释剂中研磨活性成分来将化合物1或式2的化合物和任何其他的活性成分掺入到本发明的组合物中。可通过简单地混合所述成分来制备溶液剂,包括乳油。如果意图用作乳油的液体组合物的溶剂是水不可混溶的,则通常加入乳化剂使含有活性成分的溶剂在用水稀释时发生乳化。可使用介质磨来湿磨粒径为至多2,000μm的活性成分浆液,以获得平均直径低于3μm的颗粒。可将含水浆液制备为成品悬浮浓缩物(参见例如U.S.3,060,084)或通过喷雾干燥进一步加工以形成水分散性的颗粒。干制剂通常需要干研磨步骤,其产生2至10μm范围内的平均粒径。粉剂和粉末可通过混合并且通常通过研磨(诸如用锤磨或流能磨)来制备。可通过将活性物质喷雾在预成形颗粒载体上或通过附聚技术来制备颗粒和粒料。参见Browning的“Agglomeration”(Chemical Engineering,1967年12月4日,第147-48页),Perry’s Chemical Engineer’sHandbook第4版(McGraw-Hill,New York,1963)第8-57页及其后页,以及WO 91/13546。粒料可以如U.S.4,172,714中所述来制备。可以如U.S.4,144,050、U.S.3,920,442和DE 3,246,493中所教导的来制备水分散性的和水溶性的颗粒。片剂可以如U.S.5,180,587、U.S.5,232,701和U.S.5,208,030中所教导的来制备。膜剂可以如GB 2,095,558和U.S.3,299,566中所教导的来制备。
与配制领域相关的其他信息,参见T.S.Woods的“The Formulator’s Toolbox-Product Forms for Modern Agriculture”(Pesticide Chemistry and Bioscience,TheFood-Environment Challenge),T.Brooks和T.R.Roberts编,Proceedings of the 9thInternational Congress on Pesticide Chemistry,The Royal Society of Chemistry,Cambridge,1999,第120-133页。还可参见U.S.3,235,361第6栏第16行至第7栏第19行和实施例10-41;U.S.3,309,192第5栏第43行至第7栏第62行和实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167以及169-182;U.S.2,891,855第3栏第66行至第5栏第17行和实施例1-4;Klingman的Weed Control as a Science(John Wiley and Sons,Inc.,New York,1961),第81-96页;Hance等人的Weed Control Handbook,第8版(BlackwellScientific Publications,Oxford,1989);和Developments in formulation technology(PJB Publications,Richmond,UK,2000)。
在以下实施例中,所有制剂均根据常规方法制备。无需进一步详尽说明,相信本领域技术人员使用以上所述内容可将本发明利用至最大限度。因此,以下实施例应理解为仅是例证性的,而不以任何方式限制本发明的公开内容。百分比为重量百分比,除非另外说明。
实施例A
高强度浓缩物
化合物1 98.5%
二氧化硅气凝胶 0.5%
合成无定形精细二氧化硅 1.0%
实施例B
实施例C
颗粒
化合物2b 10.0%
绿坡缕石颗粒(低挥发性物质,0.71/0.30mm;U.S.S. 90.0%No.25-50筛目)
实施例D
实施例E
可乳化浓缩物
化合物1 10.0%
聚氧乙烯山梨醇六油酸酯 20.0%
C6-C10脂肪酸甲酯 70.0%
实施例F
实施例G
实施例H
实施例I
实施例J
实施例K
实施例L
本发明的化合物表现出针对广谱的无脊椎害虫的活性。这些害虫包括栖息于各种环境中的无脊椎动物,这些环境是例如像植物叶、根、土壤、收获的作物或其他食物、建筑结构或动物体被。这些害虫包括例如以叶子(包括叶、茎、花和果实)、种子、木材、纺织纤维或动物血液或组织为食,并且从而对例如生长中或储存的农业作物、森林、温室作物、观赏植物、苗圃作物、储存的食品或纤维制品、或房屋或其他结构物或其内容物造成伤害或损害,或对动物健康或公共卫生有害的无脊椎动物。本领域技术人员会理解,并不是所有的化合物对所有害虫的所有生长阶段都同等有效。
因此,这些本发明的化合物和组合物在农业上可用于保护大田作物免受植食性无脊椎害虫,并且还非农业地用于保护其他园艺作物和植物免受植食性无脊椎害虫。该效用包括保护含有通过基因工程(即转基因的)引入或者由诱变改性的遗传物质以提供有利的性状的作物和其他植物(即农业和非农业的)。这样的性状的实例包括耐除草剂、耐植食性害虫(例如昆虫、螨、蚜虫、蜘蛛、线虫、蜗牛、植物致病真菌、细菌和病毒)、改进的植物生长、对不良生长条件如高温和低温、高或低的土壤湿度以及高盐度的提高的耐受性、增加的开花或结果、更高的收获产量、更快成熟、收获产品的更髙质量和/或营养价值、或收获产品的改善的储存或加工特性。转基因植物可以经改性以表达多种性状。含有由基因工程或诱变提供的性状的植物的实例包括表达杀虫苏云金芽孢杆菌(Bacillus thuringiensis)毒素的各种玉米、棉花、大豆和马铃薯如YIELD 和INVICTA RR2PROTM和耐受除草剂的各种玉米、棉花、大豆和油菜籽如ROUNDUPLIBERTY和以及表达N-乙酰基转移酶(GAT)以提供对草甘膦除草剂的抗性的作物,或含有提供对抑制乙酰乳酸合酶(ALS)的除草剂的抗性的HRA基因的作物。本发明的化合物和组合物可以与通过基因工程引入或通过诱变改性的性状协同地相互作用,从而增强性状的表型表达或有效性或者提高本发明的化合物和组合物的无脊椎害虫防治有效性。特别地,本发明的化合物和组合物可以与蛋白质或对无脊椎害虫有毒的其他天然产品的表型表达协同地相互作用,以提供对这些害虫的高于加合的防治。
本发明的组合物还可以任选地包含植物营养素,例如,包含至少一种选自氮、磷、钾、硫、钙、镁、铁、铜、硼、锰、锌和钼的植物营养素的肥料组合物。值得注意的是包含至少一种肥料组合物的组合物,该肥料组合物包含至少一种选自氮、磷、钾、硫、钙和镁的植物营养素。本发明的进一步包含至少一种植物营养素的组合物可以是呈液体或固体的形式。值得注意的是呈颗粒、小棒或片剂形式的固体制剂。包含肥料组合物的固体制剂可以通过将本发明的化合物或组合物与该肥料组合物和配制成分一起混合并且然后通过诸如造粒或挤出的方法制备制剂来制备。或者,固体制剂可以通过将本发明的化合物或组合物在挥发性溶剂中的溶液或悬浮液喷雾到以前制备的呈尺寸稳定的混合物形式(例如,颗粒、小棒或片剂)的肥料组合物上,并且然后蒸发溶剂来制备。
非农业用途是指除作物植物田地外的区域中的无脊椎害虫防治。本发明的化合物和组合物的非农业用途包括在储存的谷物、豆类和其他食品以及纺织品如衣物和地毯中防治无脊椎害虫。本发明的化合物和组合物的非农业用途还包括在观赏植物、森林、院落、路边和铁路用地、以及草皮如草坪、高尔夫球场和牧场中的无脊椎害虫防治。本发明的化合物和组合物的非农业用途还包括在房屋和可能被人类和/或同伴、农场、牧场、动物园或其他动物占据的其他建筑物中的无脊椎害虫防治。本发明的化合物和组合物的非农业用途还包括可能损害建筑物中使用的木材或其他结构材料的害虫诸如白蚁的防治。
本发明的化合物和组合物的非农业用途还包括通过防治寄生的或传播传染性疾病的无脊椎害虫来保护人和动物健康。对动物寄生虫的防治包括防治寄生于宿主动物身体表面(例如,肩部、腋窝、腹部、大腿内侧)的外部寄生虫和寄生于宿主动物身体内部(例如,胃、肠、肺、静脉、皮下、淋巴组织)的内部寄生虫。外部寄生虫或传播疾病的害虫包括,例如,恙螨、蜱、虱、蚊子、蝇、螨虫和跳蚤。内部寄生虫包括犬恶丝虫、钩虫和蠕虫。本发明的化合物和组合物适用于内吸和/或非内吸防治动物上寄生虫的侵袭或者感染。本发明的化合物和组合物特别适用于对抗外部寄生虫或传播疾病的害虫。本发明的化合物和组合物适用于对抗侵袭农业工作动物如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、母鸡、火鸡、鸭、鹅和蜜蜂;宠物动物和家畜如狗、猫、宠物鸟和观赏鱼;以及所谓的实验动物如仓鼠、豚鼠、大鼠和小鼠的寄生虫。通过对抗这些寄生虫,降低了死亡率和性能下降(在肉、奶、羊毛、皮肤、蛋、蜂蜜等方面),因此施用包含本发明的化合物的组合物允许更经济且简单地饲养动物。
农业或非农业无脊椎害虫的实例包括鳞翅目的卵、幼虫和成虫,如夜蛾科的粘虫、地老虎、尺蠖和棉铃虫(heliothines)(例如,粉色蛀茎虫(pink stem borer)(大螟(Sesamia inferens Walker))、玉米钻心虫(corn stalk borer)(Sesamia nonagrioidesLefebvre)、南方粘虫(southern armyworm)(南方灰翅夜蛾(Spodoptera eridaniaCramer))、秋夜蛾(fall armyworm)(草地贪夜蛾(Spodoptera frugiperda J.E.Smith))、甜菜夜蛾(beet armyworm)(甜菜夜蛾(Spodoptera exigua Hübner))、棉叶虫(cottonleafworm)(海灰翅夜蛾(Spodoptera littoralis Boisduval))、黄条粘虫(yellowstripedarmyworm)(Spodoptera ornithogalli Guenée)、小地老虎(black cutworm)(小地老虎(Agrotis ipsilon Hufnagel))、velvetbean caterpillar(藜豆夜蛾(Anticarsiagemmatalis Hübner))、绿果夜蛾(green fruitworm)(绿果冬夜蛾(Lithophane antennataWalker))、甘蓝夜蛾(cabbage armyworm)(甘蓝夜蛾(Barathra brassicae Linnaeus))、大豆尺蠖(soybean looper)(大豆尺蠖(Pseudoplusia includens Walker))、粉纹夜蛾(cabbage looper)(粉纹夜蛾(Trichoplusia ni Hübner))、烟青虫(tobacco budworm)(烟芽夜蛾(Heliothis virescens Fabricius));来自螟蛾科的螟虫、鞘蛾、结网虫、coneworms、甘蓝虫和雕叶虫(skeletonizers)(例如,欧洲玉米螟(European corn borer)(玉米螟(Ostrinia nubilalis Hübner))、脐橙螟(navel orangeworm)(Amyeloistransitella Walker))、玉米根结网虫(corn root webworm)(玉米根草螟(Crambuscaliginosellus Clemens))、草地螟(sod webworms)(螟蛾科:草螟亚科)如草地螟(sodworm)(水稻切叶野螟(Herpetogramma licarsisalis Walker))、甘蔗二点螟(sugarcanestem borer)(粟灰螟(Chilo infuscatellus Snellen))、小番茄蛀虫(tomato smallborer)(Neoleucinodes elegantalis Guenée)、绿卷叶螟(green leafroller)(稻纵卷叶螟(Cnaphalocrocis medinalis))、葡萄卷叶虫(grape leaffolder)(葡萄卷叶虫(Desmiafuneralis Hübner))、甜瓜野螟(melon worm)(瓜绢野螟(Diaphania nitidalis Stoll))、甘蓝芯蛴螬(cabbage center grub)(Helluala hydralis Guenée)、水稻三化螟(yellowstem borer)(三化螟(Scirpophaga incertulas Walker))、早期嫩梢蛀虫(early shootborer)(蔗螟(Scirpophaga infuscatellus Snellen))、白色蛀茎虫(white stem borer)(稻白螟(Scirpophaga innotata Walker))、顶部嫩梢蛀虫(top shoot borer)(甘蔗白螟(Scirpophaga nivella Fabricius))、黑头稻螟(dark-headed rice borer)(Chilopolychrysus Meyrick)、条纹稻螟(striped riceborer)(二化螟(Chilo suppressalisWalker))、卷心菜丛毛虫(cabbage cluster caterpillar)(英国大菜螟(Crocidolomiabinotalis English));卷蛾科的卷叶虫、蚜虫、种实虫和果实虫(例如,苹果蠹蛾(codlingmoth)(苹果蠹蛾(Cydia pomonella Linnaeus))、葡萄小卷叶蛾(grape berry moth)(萄果实虫主虫(Endopiza viteana Clemens))、梨小食心虫(oriental fruit moth)(东方果实蛾(Grapholita molesta Busck))、柑橘假苹果蠹蛾(citrus false codling moth)(苹果异形小卷蛾(Cryptophlebia leucotreta Meyrick))、柑橘天牛(citrus borer)(Ecdytolopha aurantiana Lima)、红带卷叶蛾(redbanded leafroller)(红带卷蛾(Argyrotaenia velutinana Walker))、斜带卷叶蛾(obliquebanded leafroller)(蔷薇斜条卷叶蛾(Choristoneura rosaceana Harris))、苹果浅褐卷叶蛾(light brown applemoth)(苹果浅褐卷蛾(Epiphyas postvittana Walker))、欧洲葡萄小卷叶蛾(Europeangrape berry moth)(女贞细卷蛾(Eupoecilia ambiguella Hübner))、苹果顶芽卷叶蛾(apple bud moth)(苹果顶芽卷叶蛾(Pandemis pyrusana Kearfott))、杂食性卷叶蛾(omnivorous leafroller)(杂食性卷叶蛾(Platynota stultana Walsingham))、葡萄褐卷蛾(barred fruit-tree tortrix)(葡萄褐卷蛾(Pandemis cerasana Hübner))、苹果褐卷叶蛾(apple brown tortrix)(苹果褐卷蛾(Pandemis heparana Denis&Schiffermüller));和许多其他经济上重要的鳞翅目(例如,小菜蛾(diamondback moth)(小菜蛾(Plutella xylostella Linnaeus))、棉红铃虫(pink bollworm)(棉红铃虫(Pectinophoragossypiella Saunders))、舞毒蛾(gypsy moth)(舞毒蛾(Lymantria dispar Linnaeus))、桃小食心虫(peach fruit borer)(桃小食心虫(Carposina niponensis Walsingham))、桃条麦蛾(peach twig borer)(桃条麦蛾(Anarsia lineatella Zeller))、马铃薯块茎蛾(potato tuberworm)(马铃薯块茎蛾(Phthorimaea operculella Zeller))、斑点绦虫状潜叶蛾(spotted teniform leafminer)(斑幕潜叶蛾(Lithocolletis blancardellaFabricius))、苹果金纹细蛾(Asiatic apple leafminer)(金纹细蛾(Lithocolletisringoniella Matsumura))、稻纵卷叶螟(rice leaffolder)(稻纵卷叶螟(Lerodea eufalaEdwards))、旋纹潜叶蛾(apple leafminer)(旋纹潜叶蛾(Leucoptera scitellaZeller));蜚蠊目的卵、若虫和成虫,包括来自姬蜚蠊科和蜚蠊科的蟑螂(例如,东方蟑螂(oriental cockroach)(东方蟑螂(Blatta orientalis Linnaeus))、亚洲蟑螂(Asiancockroach)(Blatella asahinai Mizukubo)、德国蟑螂(German cockroach)(德国小蠊(Blattella germanica Linnaeus))、褐色带蟑螂(brownbanded cockroach)(褐带皮蠊(Supella longipalpa Fabricius))、美洲蟑螂(American cockroach)(美洲大蠊(Periplaneta americana Linnaeus))、褐色蟑螂(brown cockroach)(褐色大蠊(Periplaneta brunnea Burmeister))、马德拉蟑螂(Madeira cockroach)(马德拉蜚蠊(Leucophaea maderae Fabricius))、黑胸大蠊(smoky brown cockroach)(黑胸大蠊(Periplaneta fuliginosa Service))、澳洲蟑螂(Australian Cockroach)(澳洲蟑螂(Periplaneta australasiae Fabr.))、龙虾蟑螂(lobster cockroach)(灰色蟑螂(Nauphoeta cinerea Olivier))和光滑蟑螂(smooth cockroach)(淡色歪尾蠊(Symplocepallens Stephens));鞘翅目的卵,叶子喂养、果实喂养、根喂养、种子喂养和囊泡组织喂养的幼虫和成虫,包括来自长角象虫科(Anthribidae)、豆象科(Bruchidae)和象鼻虫科(Curculionidae)的象鼻虫(例如,棉铃象虫(boll weevil)(墨西哥棉铃象(Anthonomusgrandis Boheman))、稻水象虫(rice water weevil)(稻水象甲(Lissorhoptrusoryzophilus Kuschel))、谷象(granary weevil)(谷象(Sitophilus granariusLinnaeus))、米象(rice weevil)(米象(Sitophilus oryzae Linnaeus))、早熟禾象鼻虫(annual bluegrass weevil)(早熟禾象鼻虫(Listronotus maculicollis Dietz))、早熟禾谷象甲(bluegrass billbug)(牧草长喙象(Sphenophorus parvulus Gyllenhal))、狩猎谷象(hunting billbug)(猎长喙象(Sphenophorus venatus vestitus))、丹佛谷象(Denver billbug)(丹佛长喙象(Sphenophorus cicatristriatus Fahraeus));叶甲科(Chrysomelidae)的跳甲、黄瓜叶甲、根虫、叶甲、马铃薯甲虫和潜叶虫(例如,科罗拉多马铃薯甲虫(Colorado potato beetle)(马铃薯甲虫(Leptinotarsa decemlineata Say))、西部玉米根虫(western corn rootworm)(西方玉米根虫(Diabrotica virgiferavirgiferaLeConte));来自金龟子科的金龟子和其他甲虫(例如,日本丽金龟(Japanese beetle)(日本丽金龟(Popillia japonica Newman))、东方丽金龟(oriental beetle)(东方丽金龟(Anomala orientalis Waterhouse、Exomala orientalis(Waterhouse)Baraud))、北方独角仙(northern masked chafer)(北方圆头犀金龟(Cyclocephala borealis Arrow))、南方独角仙(southern masked chafer)(南方圆头犀金龟(Cyclocephala immaculataOlivier或C.lurida Bland))、蜣螂(dung beetle)和白蛴螬(white grub)(蜉金龟属(Aphodius)物种)、草皮黑金龟(black turfgrass ataenius)(草皮黑金龟(Ataeniusspretulus Haldeman))、绿色六月金龟(green June beetle)(绿花金龟(CotinisnitidaLinnaeus))、亚洲花园甲虫(Asiatic garden beetle)(紫绒鳃角金龟(Maladera castaneaArrow))、五月/六月鳃金龟(May/June beetles)(鳃角金龟属(Phyllophaga)物种)和欧洲金龟子(European chafer)(欧洲切根鳃金龟(Rhizotrogus majalis Razoumowsky));来自皮蠹科的皮蠹;来自叩头甲科的金针虫;来自小蠹科(Scolytidae)的树皮甲虫和来自拟步甲科(Tenebrionidae)的面粉甲虫。
此外,农业和非农业害虫包括:革翅目的卵、成虫和幼虫,包括来自蠼螋科的蠼螋(例如,欧洲蠼螋(European earwig)(地蜈蚣(Forficula auricularia Linnaeus))、黑蠼螋(black earwig)(黑蠼螋(Chelisoches morio Fabricius));半翅目和同翅目的卵、幼虫、成虫和若虫,如来自盲蝽科的盲蝽(plant bugs),来自蝉科的蝉,来自大叶蝉科的叶蝉(leafhoppers)(例如,小绿叶蝉属(Empoasca)物种),来自臭虫科的臭虫(例如,温带臭虫(Cimex lectularius Linnaeus)),来自蜡蝉科和飞虱科的飞虱,来自角蝉科的角蝉,来自木虱科的木虱,来自粉虱科的粉虱,来自蚜科的蚜虫,来自根瘤蚜科的根瘤蚜,来自粉蚧科的粉蚧,来自蚧科、盾蚧科和绵蚧科的介壳虫(scales),来自网蝽科的网蝽,来自蝽科的蝽象,来自长蝽科的长蝽(chinch bugs)(例如,毛长蝽(hairy chinch bug)(美洲毛谷长蝽(Blissus leucopterus hirtus Montandon))和南部麦长蝽(southern chinch bug)(南部麦长蝽(Blissus insularis Barber))和其他来自长蝽科的长蝽(seed bugs),来自沫蝉科的沫蝉,来自缘蝽科的南瓜缘蝽,以及来自红蝽科的红蝽(red bugs)和污棉虫(cottonstainers)。
农业和非农业害虫还包括:蜱螨目(螨)的卵、幼虫、若虫和成虫,如叶螨科的叶螨(spider mites)和红螨(例如,欧洲红螨(European red mite)(苹果全爪螨(Panonychusulmi Koch))、两点叶螨(two spotted spider mite)(二斑叶螨(Tetranychus urticaeKoch))、迈叶螨(McDaniel mite)(迈叶螨(Tetranychus mcdanieli McGregor));细须螨科中的短须螨(flat mites)(例如,葡萄短须螨(citrus flat mite)(刘氏短须螨(Brevipalpus lewisi McGregor));瘿螨科中的锈螨和蚜螨,和其他叶子喂养的螨虫和在人类和动物健康方面有重要影响的螨虫,即表皮螨科(Epidermoptidae)中的尘螨、蠕形螨科(Demodicidae)中的毛囊螨、食甜螨科(Glycyphagidae)中的谷螨;硬蜱科的蜱,通常称为硬蜱(例如,鹿蜱(deer tick)(黑脚硬蜱(Ixodes scapularis Say))、澳大利亚致瘫痪蜱(Australian paralysis tick)(全环硬蜱(Ixodes holocyclus Neumann))、美洲犬蜱(American dog tick)(变异矩头蜱(Dermacentor variabilis Say))、孤星蜱(lone startick)(美洲钝眼蜱(Amblyomma americanum Linnaeus))和隐喙蜱科的蜱,通常被称为软蜱(例如,回归热蜱(relapsing fever tick)(回归热钝缘蜱(Ornithodoros turicata))、常见鸡蜱(common fowl tick(常见鸡蜱(Argas radiatus));在痒螨科、蒲螨科和疥螨科中的疥螨(scab mites)和痒螨(itch mites);直翅目的卵、成虫和幼虫,包括蚱蜢、蝗虫和蟋蟀(例如,迁徙蚱蜢(migratory grasshoppers)(例如,血黑蝗(Melanoplus sanguinipesFabricius)、殊种蝗(M.differentialis Thomas)、美洲蚱蜢(American grasshoppers)(例如,美洲沙漠蝗(Schistocerca americana Drury))、沙漠蝗(desert locust)(沙漠蝗(Schistocerca gregaria Forskal))、飞蝗(migratory locust)(飞蝗(Locustamigratoria Linnaeus))、灌木蝗(bush locust)(腺蝗属(Zonocerus)物种)、家蟋(housecricket)(家蟋(Acheta domesticus Linnaeus))、蝼蛄(mole crickets)(例如,黄褐色蝼蛄(tawny mole cricket)(黄褐色蝼蛄(Scapteriscus vicinus Scudder))和南美蝼蛄(southern mole cricket)(南美蝼蛄(Scapteriscus borellii Giglio-Tos));双翅目的卵、成虫和幼虫,包括潜叶虫(例如,斑潜蝇属(Liriomyza)物种,如蔬菜斑潜蝇(serpentinevegetable leafminer)(美洲斑潜蝇(Liriomyza sativae Blanchard))、蠓(midges)、果蝇(fruit flies)(实蝇科(Tephritidae))、麦秆蝇(frit flies)(例如,瑞典麦秆蝇(Oscinella frit Linnaeus))、土壤蛆(soil maggots)、家蝇(house flies)(例如,家蝇(Musca domestica Linnaeus))、小家蝇(lesser house flies)(例如,夏厕蝇(Fanniacanicularis Linnaeus)、小舍蝇(F.femoralis Stein))、厩螯蝇(stable flies)(例如,厩螯蝇(Stomoxys calcitrans Linnaeus))、秋家蝇(face flies)、角蝇(horn flies)、丽蝇(blow flies)(例如,金蝇属(Chrysomya)物种、伏蝇属(Phormia)物种)以及其他蝇类害虫、马蝇(horse flies)(例如,虻属(Tabanus)物种)、肤蝇(bot flies)(例如,胃蝇属(Gastrophilus)物种,狂蝇属(Oestrus)物种)、纹皮蝇(cattle grubs)(例如,牛皮蝇属(Hypoderma)物种)、鹿虻(deer flies)(例如,斑虻属(Chrysops)物种)、绵羊蜱(keds)(例如,绵羊虱蝇(Melophagus ovinus Linnaeus))以及其他短角亚目(Brachycera)、蚊子(例如,伊蚊属(Aedes)物种、按蚊属(Anopheles)物种、库蚊属(Culex)物种)、蚋(black flies)(例如,原蚋属(Prosimulium)物种、蚋属(Simulium)物种)、叮咬蠓(biting midges)、沙蝇(sand flies)、眼菌蚊(sciarids)以及其他长角亚目(Nematocera);缨翅目的卵、成虫、和幼虫,包括葱蓟马(onion thrips)(棉蓟马(Thrips tabaci Lindeman))、花蓟马(flowerthrips)(花蓟马属(Frankliniella)物种)、以及其他叶子喂养的蓟马;膜翅目的昆虫害虫,包括蚁科的蚂蚁,包括佛罗里达木蚁(the Florida carpenter ant)(佛罗里达弓背蚁(Camponotus floridanus Buckley))、红木蚁(red carpenter ant)(红木蚁(Camponotusferrugineus Fabricius))、黑木蚁(black carpenter ant)(黑木蚁(Camponotuspennsylvanicus De Geer))、白足蚁(white-footed ant)(白足蚁(Technomyrmex albipesfr.Smith))、大头蚁(big headed ants)(大头蚁属(Pheidole)物种)、幽灵蚁(ghost ant)(黑头酸臭蚁(Tapinoma melanocephalum Fabricius));法老蚁(Pharaoh ant)(小黄家蚁(Monomorium pharaonis Linnaeus))、小火蚁(little fire ant)(小火蚁(Wasmanniaauropunctata Roger))、火蚁(fire ant)(火蚁(Solenopsis geminata Fabricius))、红火蚁(red imported fire ant)(红火蚁(Solenopsis invicta Buren))、阿根廷蚁(Argentine ant)(阿根廷蚁(Iridomyrmex humilis Mayr))、疯蚁(crazy ant)(长角立毛蚁(Paratrechina longicornis Latreille))、铺道蚁(pavement ant)(草地铺道蚁(Tetramorium caespitum Linnaeus))、玉米田蚁(cornfield ant)(玉米田蚁(Lasiusalienus ))和香家蚁(odorous house ant)(家蚁(Tapinoma sessile Say))。其他膜翅目,包括蜂(包括木蜂(carpenter bees))、大黄蜂(hornets)、小黄蜂(yellowjackets)、胡蜂(wasps)和叶蜂(sawflies)(新松叶蜂属(Neodiprion)物种);茎蜂属(Cephus)物种);等翅目的昆虫害虫,包括白蚁科(Termitidae)(例如,大白蚁属(Macrotermes)物种,土白蚁(Odontotermes obesus Rambur))、木白蚁科(Kalotermitidae)(例如,堆砂白蚁属(Cryptotermes)物种)、以及鼻白蚁科(Rhinotermitidae)(例如,散白蚁属(Reticulitermes)物种,乳白蚁属(Coptotermes)物种,异白蚁属(Heterotermes tenuis Hagen))家族、东部地下白蚁(the easternsubterranean termite)(木食性散白蚁(Reticulitermes flavipes Kollar))、西部地下白蚁(western subterranean termite)(西方散白蚁(Reticulitermes hesperusBanks))、台湾乳白蚁(Formosan subterranean termite)(家白蚁(Coptotermesformosanus Shiraki))、西印度干木白蚁(West Indian drywood termite)(Incisitermesimmigrans Snyder)、粉白蚁(powder post termite)(麻头砂白蚁(Cryptotermes brevisWalker))、干木白蚁(drywood termite)(斯氏楹白蚁(Incisitermes snyderi Light))、东南部地下白蚁(southeastern subterranean termite)(美小黑散白蚁(Reticulitermesvirginicus Banks))、西部干木白蚁(western drywood termite)(西部干木白蚁(Incisitermes minor Hagen))、树栖白蚁(arboreal termites)如象白蚁属(Nasutitermes)物种的白蚁以及其他具有经济意义的白蚁;缨尾目的昆虫害虫,如蠹虫(silverfish)(衣鱼(Lepisma saccharina Linnaeus))和家衣鱼(firebrat)(家衣鱼(Thermobia domestica Packard));食毛目的昆虫害虫,包括头虱(head louse)(头虱(Pediculus humanus capitis De Geer))、体虱(body louse)(体虱(Pediculus humanusLinnaeus))、鸡体虱(chicken body louse)(Menacanthus stramineus Nitszch)、狗啮毛虱(dog biting louse)(犬毛虱(Trichodectes canis De Geer))、绒毛虱(fluff louse)(绒毛虱(Goniocotes gallinae De Geer))、羊体虱(sheep body louse)(羊虱(Bovicolaovis Schrank))、短鼻牛虱(short-nosed cattle louse)(牛血虱(Haematopinuseurysternus Nitzsch))、长鼻牛虱(long-nosed cattle louse)(牛颚虱(Linognathusvituli Linnaeus))及其他攻击人和动物的吸吮和嚼咬型寄生虱;蚤目(Siphonoptera)的昆虫害虫,包括东方鼠蚤(the oriental rat flea)(印鼠客蚤(Xenopsylla cheopisRothschild))、猫蚤(cat flea)(猫栉头蚤(Ctenocephalides felis Bouche))、犬蚤(dogflea)(犬栉首蚤(Ctenocephalides canis Curtis))、鸡蚤(hen flea)(鸡角叶蚤(Ceratophyllus gallinae Schrank))、吸着蚤(sticktight flea)(禽角头蚤(Echidnophaga gallinacea Westwood))、人蚤(human flea)(人蚤(Pulex irritansLinnaeus))以及折磨哺乳动物和禽类的其他跳蚤。所覆盖的另外节肢动物害虫包括:蜘蛛目的蜘蛛,如棕色遁蛛(the brown recluse spider)(棕隐士蛛(Loxosceles reclusaGertsch&Mulaik))和黑寡妇毒蛛(the black widow spider)(黑寡妇毒蛛(Latrodectusmactans Fabricius)),以及蚰蜒目的蜈蚣,如蚰蜒(the house centipede)(蚰蜒(Scutigera coleoptrata Linnaeus))。
存储谷物中的无脊椎害虫的实例包括平截长蠹(larger grain borer)(大谷蠹(Prostephanus truncatus))、谷蠹(lesser grain borer)(谷蠹(Rhyzoperthadominica))、米象(rice weevil)(米象(Stiophilus oryzae))、玉米象(maize weevil)(玉米象(Stiophilus zeamais))、豆象(cowpea weevil)(四纹豆象(Callosobruchusmaculatus))、赤拟谷盗(red flour beetle)(赤拟谷盗(Tribolium castaneum))、谷象(granary weevil)(Stiophilus granarius)、印度谷螟(Indian meal moth)(印度谷螟(Plodia interpunctella))、地中海面粉甲虫(Mediterranean flour beetle)(地中海粉螟(Ephestia kuhniella))和长角扁谷盗或锈扁谷盗(flat or rusty grain beetle)(锈赤扁谷盗(Cryptolestis ferrugineus))。
本发明的化合物可以具有针对线虫纲(Nematoda)、绦虫纲(Cestoda)、吸虫纲(Trematoda)和棘头纲(Acanthocephala)的成员的活性,包括经济上重要的圆线虫目(Strongylida)、蛔目(Ascaridida)、尖尾目(Oxyurida)、小杆目(Rhabditida)、旋尾目(Spirurida)和嘴刺目(Enoplida)的成员,例如但不限于经济上重要的农业害虫(即,根结线虫属(Meloidogyne)中的根结线虫(root knot nematodes)、短体线虫属(Pratylenchus)中的根腐线虫(lesion nematodes)、毛刺线虫属(Trichodorus)中的粗短根线虫(stubbyroot nematodes)等)以及动物和人类健康害虫(即,所有经济上重要的吸虫、绦虫和蛔虫,如马中的寻常圆线虫(Strongylus vulgaris)、犬中的犬弓蛔虫(Toxocara canis)、羊中的捻转血矛线虫(Haemonchus contortus)、犬中的犬恶丝虫(Dirofilaria immitis Leidy)、马中的叶状裸头绦虫(Anoplocephala perfoliata)、反刍动物中的肝片吸虫(Fasciolahepatica Linnaeus)等)。
本发明的化合物可以具有针对鳞翅目中的害虫的活性(例如,棉叶波纹夜蛾(Alabama argillacea Hübner)(棉叶虫(cotton leaf worm))、果树黄卷蛾(Archipsargyrospila Walker)(果树卷叶蛾(fruit tree leaf roller))、A.rosana Linnaeus(欧洲卷叶蛾(European leaf roller))以及其他黄卷蛾属(Archips)物种、二化螟(Chilosuppressalis Walker)(稻螟(rice stem borer))、稻纵卷叶螟(Cnaphalocrosismedinalis Guenée)(稻纵卷叶螟(rice leaf roller))、玉米根草螟(Crambuscaliginosellus Clemens)(玉米根结网虫(corn root webworm))、早熟禾草螟(Crambusteterrellus Zincken)(早熟禾草螟(bluegrass webworm))、苹果蠹蛾(Cydia pomonellaLinnaeus)(苹果蠹蛾(codling moth))、棉斑实蛾(Earias insulana Boisduval)(多刺螟蛉虫(spiny bollworm))、翠纹钻夜蛾(Earias vittella Fabricius)(斑点螟蛉虫(spotted bollworm))、棉铃虫(Helicoverpa armigera Hübner)(美洲螟蛉虫(Americanbollworm))、谷实夜蛾(Helicoverpa zea Boddie)(玉米穗蛾(corn earworm))、烟芽夜蛾(Heliothis virescens Fabricius)(烟青虫(tobacco budworm))、Herpetogrammalicarsisalis Walker(草地螟(sod webworm)、葡萄花翅小卷蛾(Lobesia botrana Denis&Schiffermüller)(葡萄小卷叶蛾(grape berry moth))、棉红铃虫(Pectinophoragossypiella Saunders)(棉红铃虫(pink bollworm))、柑橘潜叶蛾(Phyllocnistiscitrella Stainton)(柑橘潜叶蛾(citrus leafminer))、大菜粉蝶(Pieris brassicaeLinnaeus)(大白粉蝶(large white butterfly))、小菜粉蝶(Pieris rapae Linnaeus)(小白粉蝶(small white butterfly))、小菜蛾(Plutella xylostella Linnaeus)(小菜蛾(diamondback moth))、甜菜夜蛾(Spodoptera exigua Hübner)(甜菜夜蛾(beetarmyworm))、斜纹夜蛾(Spodoptera litura Fabricius)(斜纹夜蛾(tobacco cutworm,cluster caterpillar))、草地贪夜蛾(Spodoptera frugiperda J.E.Smith)(秋夜蛾(fallarmyworm))、粉纹夜蛾(Trichoplusia ni Hübner)(粉纹夜蛾(cabbage looper)和番茄斑潜蝇(Tuta absoluta Meyrick)(番茄斑潜蝇(tomato leafminer))。
本发明的化合物对来自同翅目的成员具有显著的活性,包括:豌豆蚜(Acyrthosiphon pisum Harris)(豌豆蚜(pea aphid))、黑豆蚜(Aphis craccivora Koch)(豆蚜虫(cowpea aphid))、甜菜蚜(Aphis fabae Scopoli)(蚕豆蚜(black bean aphid))、棉蚜(Aphis gossypii Glover)(棉蚜(cotton aphid,melon aphid))、苹果蚜(Aphis pomiDe Geer)(苹果蚜(apple aphid))、梨绿蚜虫(Aphis spiraecola Patch)(绣线菊蚜(spirea aphid))、茄沟无网蚜(Aulacorthum solani Kaltenbach)(毛地黄蚜(foxgloveaphid))、草莓蚜(Chaetosiphon fragaefolii Cockerell)(草莓蚜(strawberry aphid))、麦双尾蚜(Diuraphis noxia Kurdjumov/Mordvilko)(俄罗斯小麦蚜虫(Russian wheataphid))、车前圆尾蚜(Dysaphis plantaginea Paaserini)(红苹果蚜(rosy appleaphid))、苹果绵蚜(Eriosoma lanigerum Hausmann)(苹果绵蚜(woolly apple aphid))、桃大尾蚜(Hyalopterus pruni Geoffroy)(桃大尾蚜(mealy plum aphid))、萝卜蚜(Lipaphis erysimi Kaltenbach)(萝卜蚜(turnip aphid))、麦无网长管蚜(Metopolophium dirrhodum Walker)(麦蚜(cereal aphid))、马铃薯长管蚜(Macrosiphumeuphorbiae Thomas)(马铃薯蚜(potato aphid))、桃蚜(Myzus persicae Sulzer)(桃蚜(peach-potato aphid,green peach aphid))、莴苣蚜(Nasonovia ribisnigri Mosley)(莴苣蚜(lettuce aphid))、瘿绵蚜属(Pemphigus)物种(根蚜(root aphids)和倍蚜(gallaphids))、玉米蚜(Rhopalosiphum maidis Fitch)(玉米蚜(corn leaf aphid))、禾谷缢管蚜(Rhopalosiphum padi Linnaeus)(禾谷缢管蚜(bird cherry-oat aphid))、麦二叉蚜(Schizaphis graminum Rondani)(麦二叉蚜(greenbug))、麦长管蚜(Sitobion avenaeFabricius)(麦长管蚜(English grain aphid))、苜蓿斑蚜(Therioaphis maculataBuckton)(苜蓿斑蚜(spotted alfalfa aphid))、橘二叉蚜(Toxoptera aurantii Boyerde Fonscolombe)(橘二叉蚜(black citrus aphid))和褐色橘蚜(Toxoptera citricidaKirkaldy)(褐色桔蚜(brown citrus aphid));球属(Adelges)物种(球蚜(adelgids));长山核桃根瘤蚜(Phylloxera devastatrix Pergande)(山胡桃根瘤蚜(pecanphylloxera));烟粉虱(Bemisia tabaci Gennadius)(烟粉虱(tobacco whitefly),甘薯粉虱(sweetpotato whitefly))、银叶粉虱(Bemisia argentifolii Bellows&Perring)(银叶粉虱(silverleaf whitefly))、柑橘粉虱(Dialeurodes citri Ashmead)(柑橘粉虱(citrus whitefly))和温室粉虱(Trialeurodes vaporariorum Westwood)(温室粉虱(greenhouse whitefly));马铃薯小绿叶蝉(Empoasca fabae Harris)(马铃薯叶蝉(potato leafhopper))、灰飞虱(Laodelphax striatellus Fallen)(小褐飞虱(smallerbrown planthopper))、二点叶蝉(Macrolestes quadrilineatus Forbes)(紫菀叶蝉(aster leafhopper))、黑尾叶蝉(Nephotettix cinticeps Uhler)(绿叶蝉(greenleafhopper))、二条黑尾叶蝉(Nephotettix nigropictus)(稻叶蝉(riceleafhopper))、褐飞虱(Nilaparvata lugens)(褐飞虱(brown planthopper))、玉米蜡蝉(Peregrinus maidis Ashmead)(玉米飞虱(corn planthopper))、白背飞虱(Sogatellafurcifera Horvath)(白背飞虱(white-backed planthopper))、稻飞虱(Sogatodesorizicola Muir)(稻飞虱(rice delphacid))、苹果白叶蝉(Typhlocyba pomaria McAtee)(苹白小叶蝉(white apple leafhopper))、葡萄斑叶蝉属(Erythroneoura)物种(葡萄叶蝉(grape leafhoppers));十七年蝉(Magicidada septendecim Linnaeus)(周期蝉(periodical cicada));吹绵蚧(Icerya purchasi Maskell)(吹绵蚧(cottony cushionscale))、梨圆蚧(Quadraspidiotus perniciosus Comstock)(梨圆蚧(San Jose scale));臀纹粉蚧(Planococcus citri Risso)(桔粉蚧(citrus mealybug));粉蚧属(Pseudococcus)物种(其他粉蚧系群);梨木虱(Cacopsylla pyricola Foerster)(梨木虱(pear psylla))、柿木虱(Trioza diospyri Ashmead)(柿木虱(persimmon psylla))。
本发明的化合物还对来自半翅目的成员具有活性,这些成员包括:拟绿蝽(Acrosternum hilare Say)(稻绿蝽(green stink bug))、南瓜缘蝽(Anasa tristis DeGeer)(南瓜虫(squash bug))、美洲谷长蝽(Blissus leucopterus leucopterus Say)(麦长蝽(chinch bug))、温带臭虫(Cimex lectularius Linnaeus)(臭虫(bed bug))、方翅网蝽(Corythuca gossypii Fabricius)(棉网蝽(cotton lace bug))、番茄蝽(Cyrtopeltismodesta Distant)(番茄蝽(tomato bug))、棉黑翅红蝽(Dysdercus suturellus)(棉红蝽(cotton stainer))、褐臭蝽(Euschistus servus Say)(褐臭蝽(brown stink bug))、Euchistus variolarius Palisot de Beauvois(单斑蝽(one-spotted stink bug))、Graptosthetus属物种(长蝽复合体(complex of seed bugs))、茶翅蝽(Halymorpha halys)(棕色大理石纹椿(brown marmorated stink bug))、松叶根蝽(Leptoglossus corculus Say)(松叶根蝽(leaf-footed pine seed bug))、美国牧草盲蝽(Lygus lineolaris Palisot de Beauvois)(美国牧草盲蝽(tarnished plant bug))、稻绿蝽(Nezara viridula Linnaeus)(南方绿椿象(Southern green stink bug))、美洲稻蝽(Oebalus pugnax Fabricius)(稻蝽象(rice stink bug))、马利筋长蝽(Oncopeltusfasciatus Dallas)(大马利筋长蝽(large milkweed bug))、棉盲蝽(Pseudatomoscelisseriatus Reuter)(棉盲蝽(cotton fleahopper))。由本发明的化合物防治的其他昆虫目包括缨翅目(Thysanoptera)(例如,西花蓟马(Frankliniella occidentalis Pergande)(西花蓟马(western flower thrips))、桔实蓟马(Scirthothrips citri Moulton)(柑橘蓟马(citrus thrips))、大豆蓟马(Sericothrips variabilis Beach)(大豆蓟马(soybeanthrips))、以及烟蓟马(Thrips tabaci Lindeman)(洋葱蓟马(onion thrips));和鞘翅目(Coleoptera)(例如,马铃薯叶甲(Leptinotarsa decemlineata Say)(科罗拉多马铃薯甲虫(Colorado potato beetle))、墨西哥豆瓢虫(Epilachna varivestis Mulsant)(墨西哥豆瓢虫(Mexican bean beetle))以及叩甲属(Agriotes)、Athous属或丘胸叩甲属(Limonius)的金针虫)。
应注意,一些同期分类体系将同翅目归类于半翅目的亚目。
值得注意的是本发明的化合物用于防治西花蓟马(western flower thrips)(西花蓟马(Frankliniella occidentalis))的用途。值得注意的是本发明的化合物用于防治马铃薯叶蝉(potato leafhopper)(马铃薯小绿叶蝉(Empoasca fabae))的用途。值得注意的是本发明的化合物用于防治棉花蚜虫(cotton melon aphid)(棉蚜(Aphis gossypii))的用途。值得注意的是本发明的化合物用于防治桃蚜(green peach aphid)(桃蚜(Myzuspersicae))的用途。值得注意的是本发明的化合物用于防治甘薯粉虱(sweetpotatowhitefly)(烟粉虱(Bemisia tabaci))的用途。
本发明的化合物也可用于增加作物植物的活力。该方法包括使作物植物(例如,叶子、花、果实或根)或生长该作物植物的种子与化合物1或式2的化合物以足以实现期望的植物活力效果的量(即生物学有效量)接触。典型地,化合物1或式2的化合物以配制的组合物施用。虽然化合物1或式2的化合物通常直接施用于作物植物或其种子,但其也可以施用到作物植物的所在地,即作物植物的环境,特别是足够接近以使化合物1或式2的化合物迁移到作物植物上的环境部分。与该方法相关的所在地最通常包括生长介质(即,向植物提供营养物的介质),通常是其中生长植物的土壤。因此,为了增加作物植物的活力对作物植物的处理包括使作物植物、生长作物植物的种子或作物植物的所在地与生物学有效量的化合物1或式2的化合物接触。
增加作物活力可导致下列观察到的效果中的一项或多项:(a)如由优异的种子发芽、作物出苗和作物挺立展示的最佳作物培植;(b)如由快速且健康的叶生长(例如,通过叶面积指数测量)、植物高度、分蘖数(例如,对于稻)、根群和作物的营养体的总体干重展示的增强的作物生长;(c)如由开花时间、开花持续时间、花的数目、总生物质积聚(即产量)和/或果实或谷物的产品等级可销售性(即产质量)展示的改善的作物产率;(d)增强的作物耐受或预防植物病害感染和节肢动物、线虫或软体动物害虫侵袭的能力;和(e)增加的作物耐受环境胁迫,诸如暴露于极端的热量、未达到最佳标准的水分或植物性毒素化学品的能力。
相比于未经处理的植物,本发明的化合物可通过杀灭植食性无脊椎害虫或者阻止其在植物的环境中的取食而增加经处理的植物的活力。不存在植食性无脊椎害虫的这样的防治时,害虫通过消耗植物组织或汁液,或传播植物病原体诸如病毒来降低植物活力。甚至不存在植食性无脊椎害虫时,本发明的化合物可通过改变植物的代谢来增加植物活力。一般来说,如果植物生长在非理想的环境中,即包含一个或多个不利于植物实现其在理想环境中应表现出的完全遗传潜力的方面,那么作物植物的活力会通过用本发明的化合物处理该植物最显著地增加。
值得注意的是用于增加作物植物的活力的方法,其中该作物植物在包括植食性无脊椎害虫的环境中生长。还值得注意的是用于增加作物植物的活力的方法,其中该作物植物在不包括植食性无脊椎害虫的环境中生长。还值得注意的是用于增加作物植物的活力的方法,其中该作物植物在包括少于支持作物植物生长的理想水分量的水分量的环境中生长。值得注意的是用于增加作物植物的活力的方法,其中该作物是稻。还值得注意的是用于增加作物植物的活力的方法,其中该作物是玉蜀黍(玉米)。还值得注意的是用于增加作物植物的活力的方法,其中该作物是大豆。
本发明的化合物还可与一种或多种其他生物学活性化合物或生物学活性剂混合以形成多组分杀虫剂,赋予甚至更广谱的农业和非农业效用,这些生物学活性化合物或生物学活性剂包括杀昆虫剂、杀真菌剂、杀线虫剂、杀菌剂、杀螨剂、除草剂、除草剂安全剂、生长调节剂诸如昆虫蜕皮抑制剂和生根刺激剂、化学不育剂、化学信息素、拒虫剂、引诱剂、信息素、取食刺激剂、其他生物学活性化合物或昆虫病原细菌、病毒或真菌。因此本发明还涉及包含生物学有效量的化合物1或式2的化合物、至少一种附加组分和至少一种附加生物学活性化合物或生物学活性剂的组合物,该至少一种附加组分选自表面活性剂、固体稀释剂和液体稀释剂。对于本发明的混合物,可将其他生物学活性化合物或生物学活性剂与本发明的化合物(包括化合物1或式2的化合物)配制在一起以形成预混物,或者其他生物学活性化合物或生物学活性剂可与本发明的化合物(包括化合物1或式2的化合物)分开配制,并且在施用前将两种制剂组合在一起(例如在喷雾罐中),或者,依次施用。
可以配制本发明的化合物的这样的生物学活性化合物或生物学活性剂的实例是杀昆虫剂,例如阿巴美丁(abamectin)、高灭磷、灭螨醌、啶虫脒、氟丙菊酯、啶喃环丙虫酯(afidopyropen)([(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H-萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]甲基环丙烷羧酸酯)、磺胺螨酯、双甲脒、阿维菌素(avermectin)、印楝素、谷硫磷、丙硫克百威、杀虫磺、联苯菊酯、联苯肼酯、双三氟虫脲、硼酸盐、噻嗪酮、硫线磷、西维因、卡巴呋喃、杀螟丹、伐虫脒、氯虫苯甲酰胺、溴虫腈、定虫隆、毒死蜱、甲基毒死蜱、环虫酰肼、螨死净(clofentezin)、噻虫胺、氰虫酰胺(3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-1H-吡唑-5-甲酰胺)、环溴虫酰胺(3-溴-N-[2-溴-4-氯-6-[[(1-环丙基乙基)氨基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺)、乙氰菊酯、环氧虫啶((5S,8R)-1-[(6-氯-3-吡啶基)甲基]-2,3,5,6,7,8-六氢-9-硝基-5,8-环氧基-1H-咪唑并[1,2-a]吖庚因)、丁氟螨酯、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、灭蝇胺、溴氰菊酯、丁醚脲、二嗪农、狄氏剂、二氟脲、四氟甲醚菊酯、杀虫双、乐果、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、苯丁锡、杀螟硫磷、苯硫威、苯氧威、甲氰菊酯、氰戊菊酯、氟虫腈、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)、氟啶虫酰胺、氟虫酰胺、氟氰戊菊酯、嘧虫胺、氟虫脲、氟菌螨酯((αE)-2-[[2-氯-4-(三氟甲基)苯氧基]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯)、氟噻虫砜(flufensulfone)(5-氯-2-[(3,4,4-三氟-3-丁烯-1-基)磺酰基]噻唑)、氰基硫醚类杀虫剂(fluhexafon)、氟吡菌酰胺、flupiprole(1-[2,6-二氯-4-(三氟甲基)苯基]-5-[(2-甲基-2-丙烯-1-基)氨基]-4-[(三氟甲基)亚磺酰基]-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)氨基]-2(5H)呋喃酮)、氟胺氰菊酯、τ-氟胺氰菊酯、地虫硫磷、伐虫脒、噻唑磷、氯虫酰肼、heptafluthrin(2,2-二甲基-3-[(1Z)-3,3,3-三氟-1-丙烯-1-基]环丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氟铃脲、噻螨酮、氟蚁腙、吡虫啉、茚虫威、杀虫皂、异柳磷、虱螨脲、马拉硫磷、氯氟醚菊酯((1R,3S)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氰氟虫腙、蜗牛敌、甲胺磷、杀扑磷、甲硫双威、灭多虫、甲氧普林、甲氧滴滴涕、甲氧苄氟菊酯、甲氧虫酰肼、甲氧苄氟菊酯、久效磷、monofluorothrin(3-(2-氰基-1-丙烯-1-基)-2,2-二甲基环丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、烟碱、烯啶虫胺、硝乙脲噻唑、双苯氟脲、多氟脲、草氨酰、对硫磷、甲基对硫磷、扑灭司林、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯(profluthrin)、克螨特、丙苯烃菊酯(protrifenbute)、pyflubumide(1,3,5-三甲基-N-(2-甲基-1-丙酰基)-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-甲酰胺)、吡蚜酮、吡嗪氟虫腈(pyrafluprole)、除虫菊酯、哒螨灵、啶虫丙醚、新喹唑啉(间二氮杂苯)类杀虫剂(pyrifluquinazon)、嘧螨胺((αE)-2-[[[2-[(2,4-二氯苯基)氨基]-6-(三氟甲基)-4-嘧啶基]氧基]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯)、吡啶氟虫腈(pyriprole)、蚊蝇醚、鱼藤酮、利阿诺定、氟硅菊酯、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、硫丙磷、砜虫啶(N-[甲基氧化[1-[6-(三氟甲基)-3-吡啶基]乙基]-λ4-磺酰亚基]氨腈)、虫酰肼、吡螨胺、伏虫脲、七氟菊酯、特丁磷、杀虫畏、似虫菊、四氟醚菊酯(2,2,3,3-四甲基环丙烷羧酸[2,3,5,6-四氟-4-(甲氧基甲基)苯基]甲酯)、氟氰虫酰胺、噻虫啉、噻虫嗪、硫双威、杀虫双、tioxazafen(3-苯基-5-(2-噻吩基)-1,2,4-噁二唑)、唑虫酰胺、四溴菊酯、唑蚜威、敌百虫、三氟苯嘧啶(triflumezopyrim)(2,4-二氧代-1-(5-嘧啶基甲基)-3-[3-(三氟甲基)苯基]-2H-吡啶并[1,2-a]嘧啶鎓内盐)、杀铃脲、苏云金芽孢杆菌δ-内毒素、昆虫病原细菌、昆虫病原病毒和昆虫病原真菌。
值得注意的是杀昆虫剂,诸如阿巴美丁、啶虫脒、氟丙菊酯、啶喃环丙虫酯、双甲脒、阿维菌素、印楝素、丙硫克百威、杀虫磺、联苯菊酯、噻嗪酮、硫线磷、西维因、杀螟丹、氯虫苯甲酰胺、溴虫腈、毒死蜱、噻虫胺、氰虫酰胺、环溴虫酰胺、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、灭蝇胺、溴氰菊酯、狄氏剂、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、杀螟硫磷、苯硫威、苯氧威、氰戊菊酯、氟虫腈、flometoquin、氟啶虫酰胺、氟虫酰胺、氟虫脲、氟菌螨酯、氟噻虫砜、flupiprole、氟吡呋喃酮、氟胺氰菊酯、伐虫脒、噻唑磷、heptafluthrin、氟铃脲、氟蚁腙、吡虫啉、茚虫威、虱螨脲、氯氟醚菊酯、氰氟虫腙、甲硫双威、灭多虫、甲氧普林、甲氧虫酰肼、甲氧苄氟菊酯、monofluorothrin、烯啶虫胺、硝乙脲噻唑、双苯氟脲、草氨酰、pyflubumide、吡蚜酮、除虫菊酯、哒螨灵、啶虫丙醚、嘧螨胺、蚊蝇醚、利阿诺定、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、砜虫啶、虫酰肼、似虫菊、四氟醚菊酯、噻虫啉、噻虫嗪、硫双威、杀虫双、四溴菊酯、唑蚜威、三氟苯嘧啶、杀铃脲、苏云金芽孢杆菌δ-内毒素、苏云金芽孢杆菌的所有菌株以及核型多角体病毒的所有毒株。
用于与本发明的化合物混合的生物药剂的一个实施方案包括昆虫病原细菌诸如苏云金芽孢杆菌,和胶囊包封的苏云金芽孢杆菌的δ-内毒素诸如由方法制备的和生物杀昆虫剂(和是Mycogen公司,印第安纳波利斯,印第安纳州,美国(Mycogen Corporation,Indianapolis,Indiana,USA)的商标);昆虫病原真菌诸如绿僵菌;和昆虫病原(天然存在的和遗传改性的二者)病毒,包括杆状病毒、核型多角体病毒(NPV)诸如谷实夜蛾(Helicoverpa zea)核型多角体病毒(HzNPV)、芹菜夜蛾(Anagrapha falcifera)核型多角体病毒(AfNPV);和颗粒体病毒(GV),诸如苹果蠹蛾(Cydia pomonella)颗粒体病毒(CpGV)。
用于与本发明的化合物混合的生物药剂的另一实施方案包括以下之一或组合:(i)放线菌属(Actinomycetes)、土壤杆菌属(Agrobacterium)、节杆菌属(Arthrobacter)、产碱杆菌属(Alcaligenes)、金杆菌属(Aureobacterium)、固氮菌属(Azobacter)、芽孢杆菌属(Bacillus)、拜叶林克氏菌属(Beijerinckia)、慢生根瘤菌(Bradyrhizobium)、短芽胞杆菌属(Brevibacillus)、伯克氏菌属(Burkholderia)、色杆菌属(Chromobacterium)、梭菌属(Clostridium)、棒形杆菌属(Clavibacter)、丛毛单胞菌属(Comamonas)、棒状杆菌属(Corynebacterium)、短小杆菌属(Curtobacterium)、肠杆菌属(Enterobacter)、黄杆菌属(Flavobacterium)、葡糖杆菌属(Gluconobacter)、噬氢菌属(Hydrogenophaga)、克雷白氏杆菌属(Klebsiella)、甲基杆菌属(Methylobacterium)、类芽孢杆菌属(Paenibacillus)、巴斯德氏芽菌属(Pasteuria)、光杆状菌属(Photorhabdus)、叶杆菌属(Phyllobacterium)、假单胞菌属(Pseudomonas)、根瘤菌属(Rhizobium)、沙雷氏菌属(Serratia)、鞘氨醇杆菌属(Sphingobacterium)、寡养单胞菌属(Stenotrophomonas)、链霉菌属(Streptomyces)、贪噬菌属(Variovorax)或异短杆菌属(Xenorhabdus)的细菌,例如解淀粉芽孢杆菌(Bacillusamyloliquefaciens)、蜡样芽胞杆菌(Bacillus cereus)、坚强芽孢杆菌(Bacillusfirmus)、地衣芽孢杆菌(Bacillus licheniformis)、短小芽胞杆菌(Bacillus pumilus)、球形芽孢杆菌(Bacillus sphaericus)、枯草芽孢杆菌(Bacillus subtilis)、苏云金芽孢杆菌(Bacillus thuringiensis)、慢生型大豆根瘤菌(Bradyrhizobium japonicum)、活性紫色细菌(Chromobacterium subtsugae)、拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)、穿刺巴斯德氏芽菌(Pasteuria penetrans)、Pasteuria usage、荧光假单胞菌(Pseudomonasfluorescens)以及利迪链霉菌(Streptomyces lydicus)的细菌;(ii)真菌,诸如绿僵菌(green muscardine fungus);(iii)病毒,包括杆状病毒(baculovirus)、核型多角体病毒(nucleopolyhedro virus),例如谷实夜蛾(Helicoverpa zea)核型多角体病毒、芹菜夜蛾(Anagrapha falcifera)核型多角体病毒;颗粒体病毒,诸如苹果蠹蛾(Cydia pomonella)颗粒体病毒。
尤其值得注意的是其中其他无脊椎害虫防治活性成分属于与化合物或式2的化合物不同的化学类别或者具有与其不同的作用位点的组合。在某些情况下,与至少一种具有相似防治谱但是不同作用位点的其他无脊椎害虫防治活性成分的组合对于抗性管理会是特别有利的。因此,本发明的组合物还可包含生物学有效量的至少一种附加无脊椎害虫防治活性成分,该活性成分具有类似的防治谱,但是属于不同的化学类别或者具有不同的作用位点。这些附加的生物学活性化合物或生物学活性剂包括但不限于乙酰胆碱酯酶(AChE)抑制剂,诸如氨基甲酸盐灭多虫、草氨酰、硫双威、唑蚜威和有机磷酸酯毒死蜱;GABA-门控氯离子通道拮抗剂,诸如环戊二烯类杀虫剂狄氏剂和硫丹,以及苯基吡唑类乙虫腈和氟虫腈;钠通道调节剂,诸如拟除虫菊酯联苯菊酯、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;烟碱型乙酰胆碱受体(nAChR)激动剂,诸如新烟碱啶虫脒、噻虫胺、呋虫胺、吡虫啉、烯啶虫胺、硝乙脲噻唑、噻虫啉和噻虫嗪、以及砜虫啶;烟碱型乙酰胆碱受体(nAChR)变构活化剂,诸如多杀菌霉素类乙基多杀菌素和多杀菌素;氯离子通道活化剂,诸如阿维菌素阿巴美丁和埃玛菌素;保幼激素模拟物,诸如苯虫醚、甲氧普林、苯氧威和蚊蝇醚;选择性同翅目取食阻滞剂,诸如吡蚜酮和氟啶虫酰胺;螨生长抑制剂,诸如乙螨唑;线粒体ATP合酶抑制剂,如克螨特;经由质子梯度破坏的氧化磷酸化的解偶联剂,诸如溴虫腈;烟碱型乙酰胆碱受体(nAChR)通道阻滞剂,诸如沙蚕毒素类似物杀螟丹;壳多糖生物合成抑制剂,诸如苯甲酰脲氟虫脲、氟铃脲、虱螨脲、双苯氟脲、多氟脲和杀铃脲、以及噻嗪酮;双翅目蜕皮干扰剂,诸如灭蝇胺;蜕皮激素受体激动剂,诸如双酰肼类甲氧虫酰肼和虫酰肼;真蛸胺受体激动剂,诸如双甲脒;线粒体复合体III电子传递抑制剂,诸如氟蚁腙;线粒体复合体I电子传递抑制剂,诸如哒螨灵;电压依赖型钠通道阻滞剂,诸如茚虫威;乙酰CoA羧化酶抑制剂,诸如季酮酸和1,5-二氢-4-羟基-2H-吡咯-2-酮(tetramic acid)螺螨酯、螺甲螨酯和螺虫乙酯;线粒体复合体II电子传递抑制剂,诸如β-酮腈腈吡螨酯和丁氟螨酯;利阿诺定受体调节剂,诸如氨茴酸二酰胺类氯虫苯甲酰胺、氰虫酰胺和氰虫酰胺,二酰胺类,诸如氟虫酰胺,和利阿诺定受体配体,诸如利阿诺定;其中对生物活性负责的靶位点为未知或未表征的化合物,诸如印楝素、联苯肼酯、啶虫丙醚、新喹唑啉(间二氮杂苯)类杀虫剂和三氟苯嘧啶;昆虫中肠膜微生物干扰剂,诸如苏云金芽孢杆菌和它们产生的δ-内毒素以及球形芽孢杆菌(Bacillussphaericus)和生物制剂,包括核型多角体病毒(NPV)以及其他天然存在的或遗传改性的杀虫病毒。
可用本发明的化合物配制的生物学活性化合物或生物学活性剂的另外的实例是:杀真菌剂,诸如阿拉酸式苯-S-甲基、4-十二烷基-2,6-二甲基吗啉(aldimorph)、唑嘧菌胺、安美速、敌菌灵、戊环唑、嘧菌酯、苯霜灵(包括精苯霜灵)、麦锈灵、苯菌灵、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-5,6-二氢-1,4,2-噻嗪4-氧化物(bethoxazin)、乐杀螨、联苯、联苯三唑醇、联苯吡菌胺、灭瘟素、啶酰菌胺、糠菌唑、乙嘧酚磺酸酯、丁赛特、萎锈灵、环丙酰菌胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、乙菌利、氢氧化铜、氧氯化铜、硫酸铜、丁香菌酯、氰霜唑、环氟菌胺、霜脲氰、环唑醇、嘧菌环胺、抑菌灵、双氯氰菌胺、哒菌清、氯硝胺、乙霉威、恶醚唑、二氟林、甲菌定、烯酰吗啉、醚菌胺、烯唑醇(包括烯唑醇-M)、敌螨普、二噻农、二硫戊环、十二环吗啉、多果定、益康唑、乙环唑、敌瘟磷、enoxastrobin(还被称为enestroburin(烯肟菌酯))、氟环唑、噻唑菌胺、乙菌定、土菌灵、噁唑菌酮、咪唑菌酮、烯肟菌胺、氯苯嘧啶醇、腈苯唑、甲呋酰苯胺、环酰菌胺、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、胺苯吡菌酮、三苯基乙酸锡、三苯基氢氧化锡锡、福美铁、嘧菌腙、flometoquin、氟啶胺、咯菌腈、氟菌螨酯、氟吗啉、氟吡菌胺、氟吡菌酰胺、氟嘧菌酯、氟喹唑、氟硅唑、磺菌胺、氟噻菌净(flutianil)、氟酰胺、粉唑醇、氟唑菌酰胺、灭菌丹、四氯苯酞(还被称为苯酞)、麦穗宁、呋霜灵、呋吡菌胺、己唑醇、恶霉灵、双胍盐、抑霉唑、酰胺唑、烷苯磺酸盐标准品、双胍辛胺三乙酸盐、iodicarb、种菌唑、异丙噻菌胺(isofetamid)、异稻瘟净、异菌脲、丙森锌、稻瘟灵、吡唑萘菌胺、异噻菌胺、春雷霉素、克收欣、代森锰锌、双炔酰菌胺、mandestrobin、代森锰、mapanipyrin、灭锈胺、消螨多、甲霜灵(包括高效甲霜灵/精甲霜灵)、叶菌唑、磺菌威、代森联、苯氧菌胺、苯菌酮、腈菌唑、萘替芬(naftitine)、甲胂铁铵(甲基胂酸铁)、氟苯嘧啶醇、辛噻酮、呋酰胺、肟醚菌胺、恶霜灵、氟噻唑吡乙酮(oxathiapiprolin)、噁喹酸、噁咪唑、氧化萎锈灵、氧四环素、戊菌唑、戊菌隆、戊苯吡菌胺、吡噻菌胺、稻痕酯(perfurazoate)、亚磷酸(包括其盐,如三乙膦酸铝)、啶氧菌酯、粉病灵、多氧霉素、噻菌灵、咪鲜胺、腐霉利、霜霉威、丙环唑、甲基代森锌、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、嘧霉胺、啶斑肟、吡咯尼群、咯喹酮、喹唑(quinconazole)、quinmethionate、喹氧灵、五氯硝基苯、硅噻菌胺、氟唑环菌胺、硅氟唑、螺环菌胺、链霉素、硫磺、戊唑醇、特弗喹啉(tebufloquin)、teclofthalam、克枯烂、四氧硝基苯、特比萘芬、氟醚唑、噻苯哒唑、噻呋酰胺、托布津、甲基硫菌灵、福美双、噻酰菌胺、甲基立枯磷、tolprocarb、甲苯氟磺胺、三唑酮、三唑醇、嘧菌醇、唑菌嗪、三元硫酸铜、氯啶菌酯、十三吗啉、肟菌酯、氟菌唑、trimoprhamide三环唑、肟菌酯、嗪氨灵、灭菌唑、烯效唑、井冈霉素、霜霉灭(valifenalate)(还被称为valifenal)、乙烯菌核利、代森锌、福美锌、苯酰菌胺和1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异噁唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮;杀线虫剂诸如氟吡菌酰胺、螺虫乙酯、硫双威、噻唑膦、阿巴美丁、异菌脲、氟噻虫砜(fluensulfone)、二甲基二硫醚、tioxazafen、1,3-二氯丙烯(1,3-D)、威百亩(钠和钾)、棉隆、三氯硝基甲烷、苯线磷、丙线磷、硫线磷(cadusaphos)、特丁磷、新烟磷(imicyafos)、草氨酰、卡巴呋喃、tioxazafen、坚强芽孢杆菌(Bacillus firmus)和巴斯德杆菌(Pasteuria nishizawae);杀细菌剂诸如链霉素;杀螨剂,诸如双甲脒、灭螨猛、克氯苯、三环锡、三氯杀螨醇、除螨灵、乙螨唑、喹螨醚、苯丁锡、甲氰菊酯、唑螨酯、噻螨酮、克螨特、哒螨灵和吡螨胺。
在某些情况下,本发明化合物与其他生物学活性(特别是无脊椎害虫防治)化合物或剂(即活性成分)的组合可导致高于加合(即协同)的效应。降低释放在环境中的活性成分的量,同时确保有效的害虫防治一直是人们所期望的。当在施用量下发生无脊椎害虫防治活性成分的协同作用,从而赋予农业上令人满意的无脊椎害虫防治水平时,这样的组合可有利地用于降低作物生产成本并且减少环境负荷。
可以将本发明的化合物及其组合物施用至植物,这些植物经基因转化以表达对无脊椎害虫有毒的蛋白质(诸如苏云金芽孢杆菌δ-内毒素)。这样的施用可提供更广谱的植物保护,并且对于抗性管理是有利的。本发明的化合物的外源性施用的无脊椎害虫防治的作用可与表达的毒素蛋白质协同作用。
这些农用保护剂(即杀昆虫剂、杀真菌剂、杀线虫剂、杀螨剂、除草剂和生物制剂)的一般参考文献包括The Pesticide Manual[农药手册],第13版,C.D.S.Tomlin编辑,British Crop Protection Council[英国作物保护委员会],Farnham,Surrey,U.K.,2003和The BioPesticide Manual[生物农药手册],第2版,L.G.Copping编辑,British CropProtection Council,Farnham,Surrey,U.K.,2001。
在农业和非农业应用中,通过将生物学有效量的一种或多种通常为组合物形式的本发明的化合物施用到害虫环境中,包括侵害的农业和/或非农业场所,施用到要保护的区域中,或直接施用到要防治的害虫上,来防治无脊椎害虫。
因此,本发明包括在农业和/或非农业应用中防治无脊椎害虫的方法,所述方法包括使无脊椎害虫或其环境接触生物学有效量的一种或多种本发明的化合物,或接触包含至少一种此类化合物的组合物,或接触包含至少一种此类化合物和生物学有效量的至少一种附加的生物学活性化合物或药剂的组合物。包含本发明的化合物和生物学有效量的至少一种附加的生物学活性化合物或药剂的适宜组合物的实例包括颗粒状组合物,其中所述附加活性化合物存在于与本发明的化合物颗粒相同的颗粒上,或者存在于与本发明的化合物的那些颗粒不相同的颗粒上。
为了实现与本发明的化合物或组合物接触以保护田地作物免受无脊椎害虫侵害,通常在种植之前将所述化合物或组合物施用到作物种子上,施用到作物植株的叶子(例如叶片、茎杆、花朵、果实)上,或在作物种植之前或之后施用到土壤或其他生长培养基中。
接触方法的一个实施方案是通过喷雾。或者,可将包含本发明的化合物的颗粒状组合物施用到植物叶子上或土壤中。还可通过使植物与以浸壤液体制剂形式、以施用到土壤中的颗粒状制剂形式、以育苗箱处理物或移植浸泡形式施用的包含本发明的化合物的组合物接触,经由植物摄入来有效递送本发明的化合物。值得注意的是浸壤液体制剂形式的本发明的组合物。还值得注意的是防治无脊椎害虫的方法,所述方法包括使无脊椎害虫或其环境接触生物学有效量的本发明的化合物,或接触包含生物学有效量的本发明的化合物的组合物。还值得注意的是这样的方法,其中环境为土壤,并且将所述组合物作为浸壤制剂施用到土壤中。还值得注意的是,还可通过局部施用到所侵害的位置上来使本发明的化合物生效。其他接触方法包括经由直接喷雾和滞留喷雾、航空喷洒、凝胶、种子包覆、微胶囊化、全身吸收、饵料、耳标、大丸剂、喷雾、熏剂、气溶胶、粉剂以及其他许多方法,来施用本发明的化合物或组合物。接触方法的一个实施方案是尺寸上稳定的肥料颗粒、包含本发明的化合物或组合物的小块或片剂。本发明的化合物还可浸渍到用于组装无脊椎害虫防治装置(例如防昆虫网)的材料中。
本发明的化合物可用于处理所有植物、植物部分和种子。可以通过常规的繁殖和育种方法或通过基因工程方法获得植物和种子品种及栽培品种。转基因植物或种子(基因修饰植物或种子)是指将异源基因(转基因)稳定整合到植物或种子基因组中的那些植物或种子。由其在植物基因组中的特定位置定义的转基因被称为转化或转基因事件。
可以根据本发明处理的转基因植物和种子栽培种包括对一种或多种生物胁迫(例如线虫、昆虫、螨虫、真菌等)或非生物胁迫(干旱、低温、土壤盐分等)具有抗性的那些,或者包含其他理想特征的那些。可以对植物和种子进行基因修饰,使其表现出诸如除草剂耐受性、抗虫性、改良的油性(oil profile)或干旱耐受性等特征。
用本发明的化合物处理转基因植物和种子可以导致超加和或协同作用。例如,施用率的降低、活性谱的拓宽、对生物/非生物胁迫的耐受性增强或者增强的储存稳定性可能比施用本发明的化合物对转基因植物和种子的简单加和效应所预期的更大。
本发明的化合物还可用于向种子提供保护以避免无脊椎害虫侵害的种子处理物中。在本公开和权利要求上下文中,处理种子是指使种子接触通常被配制成本发明的组合物的生物学有效量的本发明的化合物。这样的种子处理物保护种子以避免无脊椎地下害虫侵害,并且一般还可保护由发芽的种子发育成的秧苗根茎和其他接触土壤的植株部分。所述种子处理物还通过使本发明的化合物或第二活性成分在发育的植株中移动,向叶子提供保护。可将种子处理物施用到各类种子上,包括可发芽形成转基因植株以表达特定特征的那些种子。代表性实例包括表达对无脊椎害虫具有毒性的蛋白质的那些,诸如苏云金芽孢杆菌毒素,或表达抗除草剂性的那些,诸如提供草甘膦抗性的草甘膦乙酰转移酶。用本发明的化合物进行种子处理也可以增加从种子生长的植物的活力。
种子处理的一种方法是在播撒种子之前,用本发明的化合物(即作为配制好的组合物)喷雾或撒粉于种子上。配制用于处理种子的组合物一般包含成膜剂或粘合剂。因此,本发明的种子包衣组合物通常包含生物学有效量的化合物1或式2的化合物,以及成膜剂或粘合剂。通过将可流动的悬浮浓缩物直接喷雾到种子滚动床中,然后将种子干燥,来将种子包衣。或者,可将其他制剂类型诸如湿粉、溶液剂、悬乳剂、乳油和乳剂的水溶液喷雾到种子上。该方法尤其可用于将膜包衣施用到种子上。本领域技术人员可采用各种包衣设备和方法。适宜的方法包括P.Kosters等人在Seed Treatment:Progress and Prospects(1994BCPC专著No.57)以及其中所列参考文献中列出的那些。
单独使用或与其他杀虫剂、杀线虫剂和杀真菌剂组合使用的化合物1或式2的化合物及其组合物特别适用于作物种子的处理,所述作物包括但不限于玉米、大豆、棉花、谷物(例如小麦、燕麦、大麦、黑麦和水稻)、马铃薯、蔬菜和油菜。
可与化合物1或式2的化合物一起配制以提供用于种子处理的混合物的其他杀虫剂包括:阿巴美丁、啶虫脒、氟丙菊酯、双甲脒、阿维菌素、印楝素、杀虫磺、联苯菊酯、噻嗪酮、硫线磷、甲萘威、克百威、杀螟丹、氯虫苯甲酰胺、虫螨腈、毒死蜱、噻虫胺、溴氰虫酰胺、氟氯氰菊酯、β-氟氯氰菊酯、氯氟氰菊酯、γ-氯氟氰菊酯、高氯氟氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、灭蝇胺、溴氰菊酯、狄氏剂、呋虫胺、二苯丙醚、甲氨基阿维菌素、硫丹、S-氰戊菊酯、乙虫腈、醚菊酯、乙螨唑、苯硫威、苯氧威、氰戊菊酯、氟虫腈、氟啶虫酰胺、氟苯虫酰胺、氟虫脲、氟胺氰菊酯、伐虫脒、噻唑膦、氟铃脲、伏蚁腙、吡虫啉、茚虫威、虱螨脲、氰氟虫腙、灭虫威(methiocarb)、灭多威、烯虫酯、甲氧虫酰肼、烯啶虫胺、硝虫噻嗪、氟酰脲、杀线威、吡蚜酮、除虫菊素、哒螨灵、三氟甲吡醚、吡丙醚、利阿诺定、乙基多杀菌素、多杀霉素、螺螨酯、螺甲螨酯、螺虫乙酯、氟啶虫胺腈、虫酰肼、胺菊酯、噻虫啉、噻虫嗪、硫双威、杀虫双、四溴菊酯、唑蚜威、杀铃脲、苏云金芽孢杆菌δ-内毒素、苏云金芽孢杆菌的所有菌株以及核型多角体病毒的所有毒株。
可与化合物1或式2的化合物一起配制以提供用于种子处理的混合物的杀真菌剂包括:吲唑磺菌胺、嘧菌酯、啶酰菌胺、多菌灵、萎锈灵、霜脲氰、环唑醇、苯醚甲环唑、烯酰吗啉、氟啶胺、咯菌腈、氟喹唑、氟吡菌胺、氟嘧菌酯、粉唑醇、氟唑菌酰胺、种菌唑、异菌脲、甲霜灵、精甲霜灵、叶菌唑、腈菌唑、多效唑(paclobutrazole)、氟唑菌苯胺、啶氧菌酯、丙硫菌唑、吡唑醚菌酯、氟唑环菌胺、硫硅菌胺、戊唑醇、噻苯唑、甲基硫菌灵、福美双、肟菌酯和灭菌唑。
用于种子处理的包含化合物1或式2的化合物的组合物可进一步包含细菌和真菌,所述细菌和真菌具有提供保护以免受植物病原性真菌或细菌和/或土壤生动物例如线虫的有害影响的能力。表现出杀线虫特性的细菌可以包括但不限于坚强芽孢杆菌、蜡样芽孢杆菌(Bacillus cereus)、枯草芽孢杆菌(Bacillius subtiliis)和穿刺芽孢杆菌(Pasteuriapenetrans)。适合的坚强芽孢杆菌菌株是CNCM I-1582(GB-126)菌株,其可以BioNemTM的形式商购获得。适合的蜡样芽孢杆菌菌株是菌株NCMM I-1592。在US 6,406,690中公开了这两种芽孢杆菌属菌株。表现出杀线虫活性的其他适合的细菌是解淀粉芽孢杆菌(B.amyloliquefaciens)IN937a和枯草芽孢杆菌(B.subtilis)GB03菌株。表现出杀真菌特性的细菌可包括但不限于短小芽孢杆菌(B.pumilus)GB34菌株。表现出杀线虫性质的真菌种类可以包括但不限于疣孢漆斑菌(Myrothecium verrucaria)、淡紫拟青霉(Paecilomyces lilacinus)和淡紫紫孢菌(Purpureocillium lilacinum)。
种子处理还可以包括一种或多种天然来源的杀线虫剂,例如被称为过敏蛋白(harpin)的激发子蛋白,其是从某些细菌植物病原体(例如梨火疫病菌(Erwiniaamylovora))中分离出来。一个实例是Harpin-N-Tek种子处理技术,其可作为N-HibitTMGold CST获得。
种子处理还可以包括一种或多种豆科植物根瘤菌,例如微共生固氮细菌日本根瘤菌(Bradyrhizobium japonicum)。这些接种物可任选地包括一种或多种脂-壳寡糖(LCO),其是在豆科植物根上形成根瘤期间由根瘤菌细菌产生的根瘤(Nod)因子。例如,品牌的种子处理技术包括LCO Promoter TechnologyTM和接种剂的结合。
种子处理还可以包括一种或多种异黄酮,它们可以增加菌根真菌的根部定植水平。菌根真菌通过增强营养物质(例如水、硫酸盐、硝酸盐、磷酸盐和金属)的根吸收来改善植物生长。异黄酮的例子包括但不限于金雀异黄素、鹰嘴豆芽素A、芒柄花素(formononetin)、黄豆苷元(daidzein)、黄豆黄素(glycitein)、橙皮素、柚皮素和红车轴草素(pratensein)。芒柄花素可作为菌根接种剂产品中的活性成分而获得,例如PHCAG。
种子处理还可以包括一种或多种植物激活剂,其在接触病原体后诱导植物的系统获得抗性。诱导这种保护机制的植物激活剂的一个实例是阿拉酸式苯-S-甲基。
处理过的种子通常包含本发明的化合物,其量为约0.1g至1kg每100kg种子(即处理前按所述种子重量计为约0.0001至1%)。用于种子处理的可流动混悬剂制剂通常包含约0.5至约70%的活性成分,约0.5至约30%的成膜粘合剂,约0.5至约20%的分散剂,0至约5%的增稠剂,0至约5%的颜料和/或染料,0至约2%的消泡剂,0至约1%的防腐剂,和0至约75%的挥发性液体稀释剂。
本发明的化合物可被掺入到饵料组合物中,所述饵料组合物可被无脊椎害虫食用,或用于装置诸如诱捕器、饵料站等中。此类饵料组合物可为颗粒形式,其包含(a)活性成分,即生物学有效量的化合物1或式2的化合物;(b)一种或多种食物物料;任选存在的(c)诱虫剂,和任选存在的(d)一种或多种湿润剂。值得注意的是颗粒或饵料组合物,其包含约0.001%至5%的活性成分,约40%至99%的食物物料和/或诱虫剂;并且任选包含约0.05%至10%的湿润剂,其可在非常低的施用率下,尤其是在摄取而不是直接接触时致命的活性成分剂量下,有效防治土壤无脊椎害虫。某些食物物料既可用作食物源,也可用作诱虫剂。食物物料包括碳水化合物、蛋白质和类脂。食物物料的实例是蔬菜粉、糖、淀粉、动物脂、植物油、酵母提取物和乳固形物。诱虫剂的实例是增味剂和香味剂,诸如水果或植物提取物、香料、或其他动物或植物组分、信息素或已知用于吸引目标无脊椎害虫的其他试剂。湿润剂即保水剂实例是乙二醇和其他多元醇、甘油和山梨醇。值得注意的是用于防治至少一种选自蚂蚁、白蚁和蟑螂的无脊椎害虫的饵料组合物(以及使用此类饵料组合物的方法)。用于防治无脊椎害虫的装置包括本发明的饵料组合物和适于容纳所述饵料组合物的外罩,其中所述外罩具有至少一个开口,所述开口的尺寸能够使无脊椎害虫通过,以使无脊椎害虫能够从位于外罩外部的位置触及所述饵料组合物,并且其中所述外罩还适于放置在潜在或已知的无脊椎害虫活动场所之中或附近。
本发明的一个实施方案涉及一种防治无脊椎害虫的方法,该方法包括用水稀释本发明的杀虫组合物(用表面活性剂、固体稀释剂和液体稀释剂配制的化合物1或式2的化合物,或者化合物1或式2的化合物与至少一种其他农药的配制混合物),并任选地添加辅剂以形成稀释组合物,并使无脊椎害虫或其环境接触有效量的所述稀释组合物。
尽管通过用水稀释足够浓度的本发明的杀虫组合物形成的喷雾组合物可以提供足够的防治无脊椎害虫的功效,但是也可以将单独配制的辅剂产品添加到喷雾罐混合物中。这些附加的辅剂通常被称为“喷雾辅剂”或“桶混辅剂”,并且包括在喷雾罐中混合以改善农药性能或改变喷雾混合物的物理性质的任何物质。辅剂可以是表面活性剂、乳化剂、石油系农作物油、农作物衍生的种子油、酸化剂、缓冲剂、增稠剂或消泡剂。辅剂用于增强功效(例如生物有效性、粘附性、渗透性、覆盖均匀性和保护的持久性),或者最小化或消除与不相容性、起泡、漂移、蒸发、挥发和降解相关的喷雾施用问题。为了获得最佳性能,根据活性成分、制剂和目标物(例如农作物、害虫)的性质选择辅剂。
在喷雾辅剂中,包括农作物油、农作物油浓缩物、植物油浓缩物和甲基化种子油浓缩物在内的油类最常用于提高农药功效,可能是通过促进更均匀的喷雾沉积物来实现的。在关注可能由油或其他与水不混溶的液体引起的植物毒性的情况下,由本发明的组合物制备的喷雾组合物通常不包含油系喷雾辅剂。然而,在由油系喷雾辅剂引起的植物毒性在商业上微不足道的情况下,由本发明的组合物的组合物制备的喷雾组合物也可以包含油系喷雾辅剂,这可能潜在地进一步提高对无脊椎害虫的防治以及耐雨性。。
被识别为“农作物油”的产品通常包含95%至98%的石蜡系或石脑油系石油以及1-2%的一种或多种用作乳化剂的表面活性剂。被识别为“农作物浓缩油”的产品通常由80%至85%的乳化石油系油和15%至20%的非离子表面活性剂组成。被正确识别为“植物油浓缩物”的产品通常包含80%至85%的植物油(即种子油或果油,最常源于棉花、亚麻籽、大豆或向日葵)和15%至20%的非离子表面活性剂。可以通过用通常来自植物油的脂肪酸甲酯代替植物油来改善辅剂性能。甲基化种子油浓缩物的实例包括浓缩物(UAP-Loveland Products,Inc.)和Premium MSO甲基化喷雾油(Helena Chemical Company)。
添加到喷雾混合物中的辅剂的量通常不超过约2.5体积%,更典型地,其量为约0.1体积%至约1体积%。添加到喷雾混合物中的辅剂的施用率通常为每公顷约1至5L。喷雾辅剂的代表性实例包括:(Syngenta)液态烃中47%的甲基化菜籽油、(Helena Chemical Company)聚环氧烷改性的七甲基三硅氧烷,和(BASF)在83%石蜡系矿物油中的17%表面活性剂混合物。
可在无其他辅剂的情况下施用本发明的化合物,但是最常见的施用是施用制剂,所述制剂包含一种或多种具有适宜载体、稀释剂和表面活性剂的活性成分,并且根据所设想的最终用途,有可能与食物组合。一种施用方法涉及将本发明的化合物的水分散体或精炼油溶液进行喷雾。与喷雾油、喷雾油浓缩液、粘展剂、辅剂、其他溶剂以及协同剂例如(胡椒基丁醚)的组合通常可增强化合物功效。就非农业用途而言,此类喷剂可从喷雾容器诸如罐、瓶或其他容器中,经由泵或通过将其从加压容器例如加压气溶胶喷雾罐中释出来施用。此类喷雾组合物可采取多种形式,例如喷剂、薄雾、泡沫、烟雾或尘雾。因此,根据具体情况,此类喷雾组合物还可包含抛射剂、发泡剂等。值得注意的是喷雾组合物,所述组合物包含生物学有效量的本发明的化合物或组合物,以及载体。此类喷雾组合物的一个实施方案包含生物学有效量的本发明的化合物或组合物,以及抛射剂。代表性的抛射剂包括但不限于甲烷、乙烷、丙烷、丁烷、异丁烷、丁烯、戊烷、异戊烷、新戊烷、戊烯、氢氟烃、氯氟烃、二甲基醚,以及前述的混合物。值得注意的是用于防治至少一种无脊椎害虫的喷雾组合物(以及使用由喷雾容器分配出的此类喷雾组合物的方法),所述无脊椎害虫选自蚊子、墨蚊、厩蝇、鹿虻、马虻、黄蜂、胡蜂、大胡蜂、壁虱、蜘蛛、蚂蚁、蚋等等,包括各种上述害虫或其组合。
下列测试证明了本发明的化合物对具体害虫的防治功效。“防治功效”表示抑制无脊椎害虫发育、导致摄食显著降低的功效(包括死亡)。然而,由所述化合物提供的害虫防治保护不限于这些物种。
本发明的生物学实施例
用于测试A-D的制剂和喷雾方法学
使用包含10%丙酮、90%水和300ppmSpreader Lo-Foam Formula非离子表面活性剂的溶液来配制测试化合物,该非离子表面活性剂包含烷基芳基聚氧乙烯、游离脂肪酸、乙二醇和异丙醇(美国科罗拉多州格里利市Loveland产品公司(LovelandIndustries,Inc.Greeley,Colorado,USA))。配制的化合物通过定位在每个测试单元的顶部上方1.27cm(0.5英寸)的具有1/8JJ定制主体的SUJ2喷雾器喷嘴(美国伊利诺斯州惠顿喷雾系统公司(Spraying Systems Co.Wheaton,Illinois,USA))以1mL的液体施用。测试化合物以指定的量被喷雾,并且每次测试重复三次。
测试A
为了通过接触和/或内吸手段评估对桃蚜(green peach aphid)(桃蚜(Myzuspersicae(Sulzer)))的防治,测试单元由内部具有12-15天龄萝卜植物的小开口容器组成。通过在测试植物的叶上,放置30-40条位于一片从栽培植物上切下的叶上的蚜虫(切叶方法)将该植物预侵袭。随着叶片脱水,蚜虫移动至测试植物上。预侵袭后,用一层沙覆盖测试单元的土壤。
配制测试化合物并且以250ppm和/或50ppm喷雾。在将配制的测试化合物喷雾后,使每个测试单元干燥1小时并且然后将黑色遮蔽盖放置在顶部上。使测试单元在19℃-21℃和50%-70%相对湿度的生长室中保持6天。然后视觉上评价每个测试单元的昆虫死亡率。
在250ppm下测试的化合物中,下列化合物导致至少80%的死亡率:1和2a。
在50ppm下测试的化合物中,下列化合物导致至少80%的死亡率:1、2a、2b和2c。
测试B
为了通过接触和/或内吸手段评估对棉花蚜虫(cotton melon aphid)(棉蚜(Aphis gossypii(Glover)))的防治,测试单元由内部具有6-7天龄棉植物的小开口容器组成。用30-40条位于根据切叶方法的一片叶上的昆虫将该植物预侵袭,并用一层沙覆盖测试单元的土壤。
配制测试化合物并且以250ppm和/或50ppm喷雾。喷雾后,使测试单元在19℃和70%相对湿度的生长室中保持6天。然后视觉上评价每个测试单元的昆虫死亡率。
在50ppm下测试的化合物中,下列化合物导致至少80%的死亡率:1、2a、2b和2c。
测试C
为了通过接触和/或内吸手段评估对甘薯粉虱(sweetpotato whitefly)(烟粉虱(Bemisia tabaci(Gennadius)))的防治,测试单元由内部具有12-14天龄棉植物的小开口容器组成。在喷雾施用之前,从植物除去两个子叶,留下一片真叶用于测定。使成年粉虱在植物上产卵并且然后从测试单元中移出。使被至少15只卵侵袭的棉植物经受喷雾测试。
配制测试化合物并且以250ppm和/或50ppm喷雾。喷雾后,使测试单元干燥1小时。然后取出圆筒,将单元取出至生长室并在28℃和50%-70%相对湿度下保持13天。然后视觉上评价每个测试单元的昆虫死亡率。
在250ppm下测试的化合物中,下列化合物导致至少50%的死亡率:1和2b。
在50ppm下测试的化合物中,下列化合物导致至少50%的死亡率:1。
测试D
为了通过接触和/或系统方式评估对西花蓟马(Frankliniellla occidentalis(Pergande))的防治,测试单元由小开口容器构成,所述小开口容器内有5-7天龄的Soleil豆类植物。
配制测试化合物,并以250ppm和/或50ppm的浓度喷雾。喷雾后,将测试单元干燥1小时,然后向每个单元中加入22-27只成体蓟马。将黑色的筛网盖放在顶部,并将测试单元在25℃和45-55%相对湿度下放置6天。
在以250ppm测试的化合物中,以下化合物具有非常好到极好水平的防治效果(30%或更少的植物破坏和/或100%的死亡率):1、2a和2b。
在以50ppm测试的化合物中,下列化合物具有非常好到极好水平的防治效果(30%或更少的植物破坏和/或100%的死亡率):1、2a和2b。
Claims (11)
2.根据权利要求1所述的化合物1。
3.根据权利要求1所述的式2的化合物,其中n为0。
4.根据权利要求1所述的式2的化合物,其中n为1。
5.根据权利要求1所述的式2的化合物,其中n为2。
6.根据权利要求1所述的化合物,其中所述化合物选自:
N-[1-(二氟甲基)环丙基]-2-(3-吡啶基)-2H-吲唑-4-甲酰胺,
N-[1,1-二甲基-2-(甲硫基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺,
N-[1,1-二甲基-2-(甲基亚磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺,和
N-[1,1-二甲基-2-(甲基磺酰基)乙基]-7-氟-2-(3-吡啶基)-2H-吲唑-4-甲酰胺;
或任何上述化合物的组合。
7.组合物,所述组合物包含根据权利要求1所述的化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选地还包含至少一种附加的生物学活性化合物或生物学活性剂。
8.根据权利要求7所述的组合物,其中所述至少一种附加的生物学活性化合物或生物学活性剂选自:阿巴美丁、高灭磷、灭螨醌、啶虫脒、氟丙菊酯、啶喃环丙虫酯、磺胺螨酯、双甲脒、阿维菌素、印楝素、谷硫磷、丙硫克百威、杀虫磺、联苯菊酯、联苯肼酯、双三氟虫脲、硼酸盐、噻嗪酮、西维因、卡巴呋喃、杀螟丹、伐虫脒、氯虫苯甲酰胺、溴虫腈、定虫隆、毒死蜱、甲基毒死蜱、环虫酰肼、螨死净、噻虫胺、氰虫酰胺、环溴虫酰胺、乙氰菊酯、环氧虫啶、丁氟螨酯、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、灭蝇胺、溴氰菊酯、丁醚脲、二嗪农、狄氏剂、二氟脲、四氟甲醚菊酯、杀虫双、乐果、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、苯丁锡、杀螟硫磷、苯硫威、苯氧威、甲氰菊酯、氰戊菊酯、氟虫腈、flometoquin、氟啶虫酰胺、氟虫酰胺、氟氰戊菊酯、嘧虫胺、氟虫脲、氟菌螨酯、氟噻虫砜、氟吡菌酰胺、flupiprole、氟吡呋喃酮、氟胺氰菊酯、τ-氟胺氰菊酯、地虫硫磷、伐虫脒、噻唑磷、氯虫酰肼、heptafluthrin、氟铃脲、噻螨酮、氟蚁腙、吡虫啉、茚虫威、杀虫皂、异柳磷、虱螨脲、马拉硫磷、氯氟醚菊酯、氰氟虫腙、蜗牛敌、甲胺磷、杀扑磷、甲硫双威、灭多虫、甲氧普林、甲氧滴滴涕、甲氧苄氟菊酯、久效磷、monofluthrin、甲氧虫酰肼、烯啶虫胺、硝乙脲噻唑、双苯氟脲、多氟脲、草氨酰、对硫磷、甲基对硫磷、扑灭司林、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯、克螨特、丙苯烃菊酯、pyflubumide、吡蚜酮、吡嗪氟虫腈、除虫菊酯、哒螨灵、啶虫丙醚、新喹唑啉(间二氮杂苯)类杀虫剂、嘧螨胺、吡啶氟虫腈、蚊蝇醚、鱼藤酮、利阿诺定、氟硅菊酯、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、硫丙磷、砜虫啶、虫酰肼、吡螨胺、伏虫脲、七氟菊酯、特丁磷、杀虫畏、似虫菊、四氟醚菊酯、噻虫啉、噻虫嗪、硫双威、杀虫双、唑虫酰胺、四溴菊酯、唑蚜威、敌百虫、杀铃脲、苏云金芽孢杆菌(Bacillus thuringiensis)的所有菌株、昆虫病原细菌、核型多角体(Nucleopolyhedrosis)病毒的所有毒株、昆虫病原病毒以及昆虫病原真菌。
9.根据权利要求7所述的组合物,其中所述至少一种附加的生物学活性化合物或生物学活性剂选自:阿巴美丁、啶虫脒、氟丙菊酯、啶喃环丙虫酯、双甲脒、阿维菌素、印楝素、丙硫克百威、杀虫磺、联苯菊酯、3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-1H-吡唑-5-甲酰胺、噻嗪酮、西维因、杀螟丹、氯虫苯甲酰胺、溴虫腈、毒死蜱、噻虫胺、氰虫酰胺、环溴虫酰胺、乙氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、λ-三氟氯氰菊酯、γ-三氟氯氰菊酯、氯氰菊酯、α-氯氰菊酯、ζ-氯氰菊酯、灭蝇胺、溴氰菊酯、狄氏剂、呋虫胺、苯虫醚、埃玛菌素、硫丹、高氰戊菊酯、乙虫腈、依芬普司、乙螨唑、杀螟硫磷、苯硫威、苯氧威、氰戊菊酯、氟虫腈、flometoquin、氟啶虫酰胺、氟虫酰胺、氟虫脲、氟菌螨酯、氟噻虫砜、flupiprole、氟吡呋喃酮、氟胺氰菊酯、伐虫脒、噻唑磷、heptafluthrin、氟铃脲、氟蚁腙、吡虫啉、茚虫威、虱螨脲、氯氟醚菊酯、氰氟虫腙、甲硫双威、灭多虫、甲氧普林、甲氧虫酰肼、甲氧苄氟菊酯、monofluthrin、烯啶虫胺、硝乙脲噻唑、双苯氟脲、草氨酰、pyflubumide、吡蚜酮、除虫菊酯、哒螨灵、啶虫丙醚、嘧螨胺、蚊蝇醚、利阿诺定、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、砜虫啶、虫酰肼、似虫菊、噻虫啉、噻虫嗪、硫双威、杀虫双、四溴菊酯、四氟醚菊酯、唑蚜威、杀铃脲、苏云金芽孢杆菌的所有菌株以及核型多角体病毒的所有毒株。
10.用于防治无脊椎害虫的方法,所述方法包括使所述无脊椎害虫或其环境与生物学有效量的根据权利要求1所述的化合物接触。
11.经处理的种子,所述经处理的种子包含按所述种子在处理之前的重量计约0.0001%至1%的量的根据权利要求1所述的化合物。
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