CN105682462A - 杀虫组合物和与其相关的方法 - Google Patents
杀虫组合物和与其相关的方法 Download PDFInfo
- Publication number
- CN105682462A CN105682462A CN201480058311.1A CN201480058311A CN105682462A CN 105682462 A CN105682462 A CN 105682462A CN 201480058311 A CN201480058311 A CN 201480058311A CN 105682462 A CN105682462 A CN 105682462A
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- China
- Prior art keywords
- methyl
- acid
- sodium
- ethyl
- ester
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 14
- -1 C1-C6Alkoxyl Chemical group 0.000 claims description 228
- 244000025254 Cannabis sativa Species 0.000 claims description 93
- 239000000460 chlorine Substances 0.000 claims description 78
- 239000002585 base Substances 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 69
- 150000001412 amines Chemical class 0.000 claims description 68
- 229910052801 chlorine Inorganic materials 0.000 claims description 58
- 239000011734 sodium Substances 0.000 claims description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 54
- 229910052708 sodium Inorganic materials 0.000 claims description 54
- 150000002148 esters Chemical class 0.000 claims description 53
- 241000894006 Bacteria Species 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 43
- 239000005864 Sulphur Substances 0.000 claims description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229910052740 iodine Inorganic materials 0.000 claims description 33
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 32
- 150000003851 azoles Chemical class 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 31
- 229910052698 phosphorus Inorganic materials 0.000 claims description 30
- 239000011574 phosphorus Substances 0.000 claims description 30
- 241000238631 Hexapoda Species 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 239000011591 potassium Substances 0.000 claims description 26
- 229910052700 potassium Inorganic materials 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 22
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000003513 alkali Substances 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 17
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- QSLMSOBCWZNNCH-UHFFFAOYSA-N tert-butyl carbamoperoxoate Chemical class CC(C)(C)OOC(N)=O QSLMSOBCWZNNCH-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 14
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 claims description 12
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 claims description 12
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 11
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 11
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 229940124530 sulfonamide Drugs 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 10
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 229930192474 thiophene Natural products 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 150000007857 hydrazones Chemical class 0.000 claims description 8
- 239000002917 insecticide Substances 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 8
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims description 7
- 239000005644 Dazomet Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005805 Mepanipyrim Substances 0.000 claims description 7
- UDSJPFPDKCMYBD-UHFFFAOYSA-N Metsulfovax Chemical compound S1C(C)=NC(C)=C1C(=O)NC1=CC=CC=C1 UDSJPFPDKCMYBD-UHFFFAOYSA-N 0.000 claims description 7
- WHDHEVMINMZADQ-UHFFFAOYSA-N [F].N1C=CC=C1 Chemical compound [F].N1C=CC=C1 WHDHEVMINMZADQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 7
- 229960002125 enilconazole Drugs 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000002316 fumigant Substances 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 claims description 7
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002923 oximes Chemical class 0.000 claims description 7
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 6
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 6
- MLDVVJZNWASRQL-UHFFFAOYSA-N 4-diethoxyphosphinothioyloxy-n,n,6-trimethylpyrimidin-2-amine Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(N(C)C)=N1 MLDVVJZNWASRQL-UHFFFAOYSA-N 0.000 claims description 6
- BIHPYCDDPGNWQO-UHFFFAOYSA-N 5-iai Chemical compound C1=C(I)C=C2CC(N)CC2=C1 BIHPYCDDPGNWQO-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- LVPGGWVHPIAEMC-UHFFFAOYSA-L Morfamquat Chemical compound [Cl-].[Cl-].CC1COCC(C)N1C(=O)C[N+]1=CC=C(C=2C=C[N+](CC(=O)N3C(COCC3C)C)=CC=2)C=C1 LVPGGWVHPIAEMC-UHFFFAOYSA-L 0.000 claims description 6
- CVRALZAYCYJELZ-UHFFFAOYSA-N O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate Chemical compound C=1C=CC=CC=1P(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl CVRALZAYCYJELZ-UHFFFAOYSA-N 0.000 claims description 6
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 claims description 6
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 6
- NDYULEPTCXJCJM-UHFFFAOYSA-N dazomet, sodium salt Chemical compound [Na+].CN1CN(C)C(=S)S[CH-]1 NDYULEPTCXJCJM-UHFFFAOYSA-N 0.000 claims description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 6
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 238000009333 weeding Methods 0.000 claims description 6
- 239000000080 wetting agent Substances 0.000 claims description 6
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 claims description 6
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 5
- QQHRSBLQLJPBPJ-UHFFFAOYSA-N (2,4-dinitro-6-pentan-2-ylphenyl) propan-2-yl carbonate Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C QQHRSBLQLJPBPJ-UHFFFAOYSA-N 0.000 claims description 5
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 5
- OZOMQRBLCMDCEG-VIZOYTHASA-N 1-[(e)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N\N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-VIZOYTHASA-N 0.000 claims description 5
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims description 5
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-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
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- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
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- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
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Classifications
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- 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
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- A01C1/06—Coating or dressing seed
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
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- A—HUMAN NECESSITIES
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
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- A—HUMAN NECESSITIES
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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Abstract
杀虫组合物包含式I化合物或其任何农业上可接受的盐,其中R1、R2、R4、R5、R6、R7、Z、Q和Y如本申请所定义。防治害虫的方法包括将杀虫组合物施用于害虫群体附近或者施用至防治害虫的区域。
Description
优先权要求
本申请要求2013年10月22日提交的题为“PESTICIDALCOMPOSITIONSANDRELATEDMETHODS”的美国临时专利申请61/894,281提交日的优先权。
技术领域
本申请涉及具有对抗线虫门、节肢动物门、和/或软体动物门害虫的杀虫效用的化合物、制备这样的化合物的方法、以及用于这样的方法的中间体的领域。这些化合物可以用作,例如,杀线虫剂,杀螨剂,杀昆虫剂,杀螨剂,和/或杀软体动物剂。
背景技术
防治害虫群体对于人类健康、现代农业、食物储存、和卫生都是必要的。已经有超过一万种害虫导致农业损失,每年全球农业损失总计达数十亿美元。因此,一直需要新型杀虫剂以及制备和使用这些杀虫剂的方法。
具体实施方式
定义
在定义中给出的实例通常是非穷举性的且不能被解释为对本申请公开的发明进行限制。应该理解的是,取代基应该符合化学键合规则及就与其连接的特定分子而言符合立体化学相容性限制。
“烷基”表示且包括非环状的饱和的支链或非支链的烃。非限制性实例可以包括甲基、乙基、丙基、异丙基、1-丁基、2-丁基、异丁基、叔丁基、戊基、2-甲基丁基、1,1-二甲基丙基、己基、庚基、辛基、壬基、或癸基。
“环烷基”表示且包括单环或多环的饱和烃。非限制性实例可以包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环癸基、降冰片基、二环[2.2.2]辛基、或十氢萘基。
“链烯基”表示且包括包含至少一个碳-碳双键的非环状的、支链或非支链的烃。非限制性实例可以包括乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、或癸烯基。
“环烯基”表示且包括包含至少一个碳-碳双键的单环或多环的烃。非限制性实例可以包括环戊烯基、环己烯基、环庚烯基、环辛烯基、或环癸烯基。
“炔基”表示且包括包含至少一个碳-碳叁键的非环状的、支链或非支链的烃。非限制性实例可以包括乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、或癸炔基。
“环炔基”表示且包括包含至少一个碳-碳叁键的单环或多环的烃。非限制性实例可以包括环庚炔基、环辛炔基、或环癸炔基。
“芳基”表示且包括具有或不具有任何取代的芳族化合物。非限制性实例可以包括苯基或萘基。
“烷氧基”表示且包括包含至少一个碳-氧单键的烷基。非限制性实例可以包括甲氧基、乙氧基、丙氧基、丁氧基、环丙氧基、环丁氧基、或环戊氧基。
“链烯氧基"表示且包括包含至少一个碳-氧单键的链烯基。非限制性实例可以包括烯丙基氧基、丁烯基氧基、戊烯基氧基、己烯基氧基、庚烯基氧基、辛烯基氧基、壬烯基氧基、或癸烯基氧基。
“炔氧基”表示且包括包含至少一个碳-氧单键的炔基。非限制性实例可以包括戊炔基氧基、己炔基氧基、庚炔基氧基、辛炔基氧基、壬炔基氧基、或癸炔基氧基。
“环烷氧基”表示且包括包含至少一个碳-氧单键的环烷基。非限制性实例可以包括环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环庚基氧基、环辛基氧基、环癸基氧基、降冰片基氧基、或二环[2.2.2]辛基氧基。
“卤代环烷基”表示且包括包含碳、卤素、和氢的单环或多环的饱和的取代基。非限制性实例可以包括1-氯环丙基、1-氯环丁基、或1-二氯环戊基。
“环链烯氧基”表示且包括进一步含有碳-氧单键的环链烯基。非限制性实例可以包括环丁烯基氧基、环戊烯基氧基、环己烯基氧基、环庚烯基氧基、环辛烯基氧基、环癸烯基氧基、降冰片烯基氧基、或二环[2.2.2]辛烯基氧基。
“烷基硫基”表示且包括包含至少一个碳-硫单键的烷基。
“卤代烷基硫基”表示且包括包含至少一个碳-硫单键和卤素原子的烷基。
“卤代”或“卤素”表示且包括氟、氯、溴、或碘。
“卤代烷基”表示且包括取代有至少一个卤素原子的烷基。
“卤代烷氧基”表示且包括取代有至少一个卤素原子的烷氧基。
“杂原子”表示且包括硫(S)原子、氧(O)原子、或(N)原子。
“杂烷基”表示且包括包含至少一个硫(S)原子、氧(O)原子、或(N)原子的烷基。
“杂环基”表示环状取代基,其可为完全饱和、部分不饱和或完全不饱和的,其中所述环状结构含有至少一个碳和至少一个杂原子,其中所述杂原子为氮、硫或氧。在硫的情况中,该原子可为其它氧化态,例如亚砜和砜。芳族杂环基的实例包括但不限于苯并呋喃基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、苯并噻吩基、苯并噻唑基、噌啉基、呋喃基、咪唑基、吲唑基、吲哚基、异吲哚基、异喹啉基、异噻唑基、异噁唑基、噁二唑基、噁唑啉基、噁唑基、酞嗪基、吡嗪基、吡唑啉基、吡唑基、哒嗪基、吡啶基、嘧啶基、吡咯基、喹唑啉基、喹啉基、喹喔啉基、四唑基、噻唑啉基、噻唑基、噻吩基、三嗪基,和三唑基。完全饱和杂环基的实例包括但不限于哌嗪基、哌啶基、吗啉基、吡咯烷基、氧杂环丁烷基、四氢呋喃基、四氢噻吩基和四氢吡喃基。部分不饱和杂环基的实例包括但不限于1,2,3,4-四氢喹啉基、4,5-二氢-噁唑基、4,5-二氢-1H-吡唑基、4,5-二氢-异噁唑基,和2,3-二氢-[1,3,4]-噁二唑基。另外的实例包括下面的
硫杂环丁烷基S-氧代-硫杂环丁烷基S,S-二氧代-硫杂环丁烷基。
“杀虫有效量”表示且包括可对至少一种昆虫产生不良影响的活性物质的量,其中不良影响可能包括偏离自然发育(naturaldevelopment),杀死,调节等。
“防治”或其语法变体表示且包括调节活昆虫的数目或调节昆虫的发育卵的数目或两者。
“协同作用”或其语法变体表示且包括两种或更多种活性药剂的组合中所遇到的共同作用,其中两种或更多种活性药剂的组合活性超过每种活性化合物单独活性的总和。
杀虫化合物
在一种特定的实施方式中,杀虫组合物包含式I化合物或其任何农业上可接受的盐:
其中:
R1、R2和R4独立地为氢、F、Cl、Br、I、取代或未取代的C1-C6烷基、或取代或未取代的C1-C6卤代烷基、C3-C10环烷基、或C3-C10卤代环烷基、C2-C6烯基、C2-C6炔基,其中所述R1、R2和R4当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C3-C10环烷基、或C3-C10卤代环烷基,其各自可以为经取代的并且可以任选取代有R10;
R3为氢、F、Cl、Br、I、CN、NO2、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、C2-C6炔基、取代或未取代的C1-C6烷氧基、取代或未取代的C3-C10环烷基、取代或未取代的C1-C6卤代烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、OR10、C(=X1)R10、C(=X1)OR10、C(=X1)N(R10)2、N(R10)2、N(R10)C(=X1)R10、SR10、S(O)nOR10或R10S(O)nR10、其中所述R3当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基或C1-C20杂环基,其各自可以为经取代的,并且可以任选取代有R10;
R5选自氢、F、Cl、Br、I、CN、NO2、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、C3-C10环烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、OR10、C(=X1)R10、C(=X1)OR10、C(=X1)N(R10)2、N(R10)2、N(R10)C(=X1)R10、S(O)nR10、S(O)nOR10或R10S(O)nR10,其中所述R5当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基或C1-C20杂环基,其各自可以为经取代的,并且可以任选取代有R10;
Y为键或者为取代或未取代的C1-C6烷基、或取代或未取代的C2-C6烯基,
其中,除了当Y为键的情况,其中Y当被取代时各自具有一个或多个选自以下的取代基:氢、F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基或C3-C10环烷基;任选地,Y和R7可以以环状排列连接,其中任选地这样的排列可以在连接Y和R7的环状结构中具有一个或多个选自以下的杂原子:O、S或N;
R6选自氢、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C2-C6炔基、取代或未取代的C3-C10环烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、C1-C6烷基C6-C20芳基(其中所述烷基和芳基可以独立地为取代的或未取代的)、其中烷基和卤代环烷基可以独立地为取代的或未取代的C1-C6烷基-(C3-C10卤代环烷基),或其中所述烷基和环烷基可以独立地为取代的或未取代的C1-C6烷基-(C3-C10环烷基),其中R6当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C1-C6烷氧基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基、C1-C20杂环基或R10芳基,其各自可以为经取代的,并且可以任选地取代有R10;
R7为R9或R8S(O)nR9;
R8为取代或未取代的C2-C12烯基、取代或未取代的C1-C12烷基、取代或未取代的C3-C10环烷基、或取代或未取代的C1-C10杂环基,其中所述R8当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、OR10、S(O)nR10、C6-C20芳基或C1-C20杂环基,其各自可以为经取代的,并且可以任选地取代有R10;
R9选自氢,取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、取代或未取代的C3-C10环烷基、取代或未取代的卤代烷基、取代或未取代的C3-C10卤代环烷基、取代或未取代的C3-C10环烯基、取代或未取代的C6-C20芳基、或取代或未取代的C1-C20杂环基,其中所述R9当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、氧代基团、OR10、S(O)nR10、C6-C20芳基或C1-C20杂环基,其各自可以为经取代的,并且可以任选地取代有R10;
R10选自氢、CN、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、取代或未取代的C2-C6烯氧基、取代或未取代的C3-C10环烷基、取代或未取代的C3-C10环烯基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、取代或未取代的S(O)nC1-C6烷基、或取代或未取代的N(C1-C6烷基)2,其中所述R10当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OC1-C6烷基、OC1-C6卤代烷基、S(O)nC1-C6烷基、S(O)nOC1-C6烷基、C6-C20芳基或C1-C20杂环基;
Q和X1独立地为氧(O)或硫(S);
n为0、1或2;和
Z为N或C-R3。
在另一种实施方式中,R1、R2和R4为氢。
在另一种实施方式中,R3为氢、F、Cl、Br或I,优选为氢或F。
在另一种实施方式中,R5选自F、Cl、Br、I、或未经取代的C1-C6烷基,优选地为Cl或CH3。
在另一种实施方式中,Y-C≡C-R6为CH2C≡CH或CH(CH3)C≡CH。
在另一种实施方式中,R7为(C1-C6)烷基S(O)n(C1-C6)烷基、(C1-C6)烷基S(O)n(C1-C6)卤代烷基或(C1-C6)烷基S(O)n(C1-C6)烷基(C3-C6)卤代环烷基。
Q和X1独立地为氧(O)。
n为0或1。
Z为C-R3。
在一种实施方式中,式I化合物(其中Y为取代或未取代的C1-C6烷基、或取代或未取代的C2-C6烯基)可以如方案1所示进行制备。
方案1
在方案1的步骤a中,氨基甲酸叔丁氧基酯化合物1-1(如在PCT申请号WO2010/129497A1中所描述的进行制备)可以在非质子溶剂中于约-78℃至约120℃的温度以碱处理,接着与亲电子试剂1-2(其中LG可以为卤素,如Cl、Br和I、或者磺酸烷基酯或磺酸芳基酯,并且其中Y为取代或未取代的C1-C6烷基或取代或未取代的C2-C6烯基)反应,得到噻唑化合物1-3。合适的非质子溶剂的非限制性实例可以包括N,N-二甲基甲酰胺(DMF)、四氢呋喃(THF)、二噁烷、二甲基亚砜(DMSO)、二甘醇二甲醚(diglyme)、乙二醇二甲醚(monoglyme)或N-甲基吡咯烷酮(NMP)。合适的碱的非限制性实例可以包括氢化钠、叔丁醇钾、烷基锂试剂如t-BuLi、n-BuLi和烷基镁卤化物,或其他金属氢化物。
在方案1的步骤b中,噻唑化合物1-3可以与酸如氯化氢在溶剂如二噁烷中反应得到相应的盐如HCl盐1-4。其他合适的酸的非限制性实例可以包括三氟乙酸(TFA)、溴化氢(HBr)或者无机酸如硫酸(H2SO4)。
在方案1的步骤c中,胺1-4可以用酰氯或酸酐1-5在碱如三乙胺或N,N’-4-二甲基氨基吡啶(DMAP)的存在下在非质子溶剂如二氯甲烷(CH2Cl2)中于约-80℃至约100℃的温度进行处理,得到相应的式(I)化合物。其他合适的碱的非限制性实例可以包括Hünig’s碱、金属氢化物或碱金属氢氧化物。
备选地,在方案1的步骤c中,噻唑1-4可以用酸化合物1-5(其中X为OH)在酰胺偶联试剂如1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC)、二环己基碳二亚胺(DCC)或二异丙基碳二亚胺(DIC)和碱如DMAP或三乙胺的存在下在非质子溶剂如CH2Cl2或DMF中进行处理,得到式I化合物。
在一种实施方式中,式2-6的化合物(其中Z为N、CH或CF,R5为甲基或Cl,且R6为氢或甲基,n′为1或2)可以如方案2中所示出的进行制备。
方案2
氨基甲酸叔丁氧基酯化合物(2-1)可以如PCT申请号WO2010/129497A1中所描述的进行制备,其中Z为CF、R5为甲基或Cl。氨基甲酸叔丁氧基酯(2-1)可以如PCT申请号WO2010/129497A1中所描述的进行制备,其中Z为CH且R5为甲基。氨基甲酸叔丁氧基酯(2-1)可以根据方案4制备,其中Z为CH且R5为Cl。氨基甲酸叔丁氧基酯(2-1)可以如PCT申请号WO2010/129497A1中所描述的进行制备,其中Z为N且R5为甲基。氨基甲酸叔丁氧基酯(2-1)可以如PCT申请号WO2010/129497A1或方案4中所描述的进行制备,其中Z为N且R5为Cl。
在方案2的步骤a中,一当量的氨基甲酸叔丁氧基酯化合物(2-1)(Z=N、CH或CF;R5=Me或Cl)可以在非质子溶剂如DMF(约0.01M至约4M的浓度)中于约-78℃至约120℃的温度以碱如氢化钠(约0.9当量至约1.2当量)处理,接着添加亲电子试剂(2-2)(其中R6为氢或甲基(约0.9当量至约4当量),其中LG可以为卤素如Cl、Br和I,或甲磺酸酯或其他离去基团),得到酰胺化合物(2-3)(Z=N、CH或CF;R5=Me或Cl;R6=H或Me)。其他合适溶剂的非限制性实例可以包括THF、二噁烷、DMSO、二甘醇二甲醚、乙二醇二甲醚或NMP。其他合适的碱的非限制性实例可以包括叔丁醇钾、烷基锂试剂如t-BuLi、n-BuLi、烷基镁卤化物或其他金属氢化物。
在方案2的步骤b中,一当量的酰胺化合物(2-3)(Z=N或CH或CF;R5=Me或Cl;R6=H或Me)可以在溶剂如二噁烷(浓度为约0.001M至约10M)中以酸如HCl(约1mol当量至约100mol当量)进行处理,得到对应的HCl盐(2-4)(Z=N、CH或CF;R5=Me或Cl;R6=H或Me)。其他合适的酸的非限制性实例可以包括TFA、HBr或无机酸如H2SO4。可以理解的是,HCl盐(2-4)可以为游离碱,所得胺可以适于后续化学操作。
在方案2的步骤c中,该HCl盐(2-4)(Z=N、CH或CF;R5=Me或Cl,R6=H或Me)可以在碱如三乙胺(约2当量至约10当量)的存在下在非质子溶剂如CH2Cl2(浓度为约0.001M至约5M)中于约-80℃至约100℃的温度以约1当量至4约当量的2-5(其中x为Cl)处理,得到对应的酰胺化合物(2-6)。其他合适的碱的非限制性实例可以包括Hünig’s碱、金属氢化物或金属氢氧化物。
在一种实施方式中,式3-2化合物可以如方案3所示进行制备。
方案3
在方案3的步骤a中,亚砜或砜化合物3-1(Z=N、CH或CF;R5=Me或Cl;R6=Me或H;n=1或2;n′=1或2)可以通过使1当量的对应硫化物化合物2-6(Z=N、CH或CF;R5=Me或Cl,n′=1或2)分别与约1当量或约2.0至2.5当量的氧化剂如NaBO3·4H2O在溶剂如乙酸(浓度为约0.001M至2M)中于约-20℃至约120℃的温度反应而制备,如在PCT申请号WO2010/129497A1中所描述的。
在方案3的步骤c中,酰胺化合物2-6(Z=N、CH或CF;R5=Me或Cl,R6=H或Me;n′=1、2)可以通过与硫源如劳氏试剂(约1当量至约10当量)在溶剂如二甘醇二甲醚(浓度为约0.001M至约5M)的存在下于约-20℃至约200℃的温度的反应而转化成对应的硫酰胺化合物3-2(Z=N、CH或CF;R5=Me或Cl,R6=H或Me;n′=1或2)。
备选地,如方案3的步骤b所示,亚砜或砜3-1(Z=N、CH或CF;R5=Me或Cl,R6=H、Me;n=1或2;n′=1或2)可以在溶剂如二甘醇二甲醚(浓度为约0.001M至约5M)中于约-20℃至约200℃的温度以硫源如劳氏试剂(约1当量至约10当量)处理,得到硫酰胺化合物3-3(Z=N、CH或CF;R5=Me或Cl,R6=H或Me;n=1或2;n′=1或2)。
在一种实施方式中,式1A的化合物可以如方案4中所示进行制备。
方案4
在方案4的步骤a中,噻唑化合物C1可以通过使噻唑化合物C0与氯化试剂如N-氯琥珀酰亚胺在溶剂如乙腈中于约65℃的温度反应而制备。
在方案4的步骤b中,化合物C1的一个Boc保护基团可以通过以酸如三氟乙酸(TFA)在极性非质子溶剂如CH2Cl2中于环境温度进行处理而除去,得到噻唑化合物C2。
在方案4的步骤c中,噻唑化合物C3可以通过使N-Boc-保护的氨基甲酸酯化合物C2在极性非质子溶剂如DMF中于约-20℃至约50℃的温度与碱如氢化钠反应并且然后与亲电子试剂如3-溴丙-1-炔反应而制备。
在方案4的步骤d中,噻唑化合物C3的Boc保护基团可以通过以强酸如氢氯酸在二噁烷中进行处理来除去,得到4-氯-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺(C4)的相应的盐如HCl盐。
在方案4的步骤e中,4-氯-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺HCl盐(C4)可以与3-(甲硫基)丙酰氯在溶剂如四氢呋喃(THF)中在碱如DMAP的存在下于约-20℃至约60℃的温度反应,得到化合物(IA)。
在一种实施方式中,式1-3的化合物可以如方案5中所示进行制备。
方案5
在方案5的步骤a中,式5-1的酸化合物(其中R5为Me或Cl)可以用二苯基磷酰基叠氮化物(DPPA)和碱如三乙胺在非质子溶剂如甲苯中于室温进行处理,得到对应的酰基叠氮化物5-2。在方案5的步骤b中,式5-2的酰基叠氮化物可以在醇如叔丁醇的存在下加热至约100℃,得到对应的式5-3的氨基甲酸叔丁基酯。在方案5的步骤c中,式5-3的氨基甲酸叔丁基酯可以在非质子溶剂中于约-78℃至约120℃的温度以碱处理,接着与亲电子试剂1-2(其中LG可以为卤素如Cl、Br和I,或磺酸烷基酯或磺酸芳基酯)反应,得到噻唑化合物5-4。合适的非质子溶剂的非限制性实例可以包括N,N-二甲基甲酰胺(DMF)、四氢呋喃(THF)、二噁烷、二甲基亚砜(DMSO)、二甘醇二甲醚、乙二醇二甲醚或N-甲基吡咯烷酮(NMP)。合适的碱的非限制性实例可以包括氢化钠、叔丁醇钾、烷基锂试剂如t-BuLi、n-BuLi和烷基镁卤化物或其他金属氢化物。在方案5的步骤d中,可以允许式5-4的噻唑化合物(其中R5和R6如前文所定义)在Suzuki偶联条件下与式5-5的硼酸(其中Z、R1、R2和R4如前文所定义)反应,得到式1-3的噻唑。
杀虫可接受的酸加成盐、盐衍生物、溶剂化物、酯衍生物、多晶型物、同位素、放射线核素和立体异构体
在一些实施方式中,式I化合物可配制为杀虫可接受的酸加成盐。通过非限制性实例,胺官能团可与以下酸形成盐:盐酸、氢溴酸、硫酸、磷酸、乙酸、苯甲酸、枸橼酸、丙二酸、水杨酸、苹果酸、富马酸、草酸、琥珀酸、酒石酸、乳酸、葡糖酸、抗坏血酸、马来酸、天冬氨酸、苯磺酸、甲磺酸、乙磺酸、羟基甲磺酸、羟基乙磺酸和三氟乙酸。另外,通过非限制性实例,酸官能团可形成盐,包括从碱金属或碱土金属得到的那些盐和从氨和胺得到的那些盐。优选的阳离子的实例包括钠阳离子、钾阳离子和镁阳离子
在一些实施方式中,式I化合物可配制为盐衍生物。通过非限制性实例,盐衍生物可通过使游离碱与足量所期望的酸接触,从而得到盐来制备。游离碱可如下重新得到:所述盐用合适的稀碱水溶液诸如稀氢氧化钠(NaOH)水溶液、稀碳酸钾水溶液、稀氨水溶液和稀碳酸氢钠水溶液处理。作为实例,在许多情况下,杀虫剂诸如2,4-D通过将其转化为其二甲胺盐来变得更具水溶性。
在一些实施方式中,式I化合物可配制为与溶剂分子形成稳定的复合物(complex),所述复合物在除去非复合的溶剂分子后保持完整。这些复合物通常称为“溶剂化物”。然而,特别期望的是与作为溶剂分子的水形成稳定的水合物。
在一些实施方式中,式I化合物可配制为酯衍生物。然后,这些酯衍生物可按与本文中公开的本发明的施用方式相同的方式施用。
在一些实施方式中,式I化合物可配制为各种结晶多晶型物。多晶型现象在农药的开发中是重要的,这是因为相同分子的不同结晶多晶型物或结构可具有非常不同的物理性质和生物性能。
在一些实施方式中,式I化合物可用不同的同位素制备。特别重要的是具有2H(也称为氘)代替1H的分子。
在一些实施方式中,式I化合物可用不同的放射性核素制备。特别重要的是具有13C或14C的分子。
在一些实施方式中,式I化合物可按一种或多种立体异构体的形式存在。因此,某些分子可制备为外消旋混合物。本领域技术人员应该理解的是,一种立体异构体可能比其它立体异构体更具活性。单一立体异构体可如下得到:已知的选择性的合成方法、使用拆分起始原料的常规合成方法或常规的拆分方法。本文中披露的某些分子可作为两种或者更多种异构体存在。各种异构体包括几何异构体、非对映异构体,和对映异构体。因此,本文中披露的分子包括几何异构体、外消旋混合物、单个立体异构体,和光学活性混合物。本领域技术人员应承认的是,一种异构体可比其它异构体更有活性。为清楚起见,本公开中披露的结构仅以一种几何形式描绘,但是意在代表分子的所有几何形式。
杀虫组合物
在一种特定的实施方式中,杀虫组合物包含式I化合物或其任何农业上可接受的盐。
在一些实施方式中,杀虫组合物包含式I化合物或其任何农业上可接受的盐、植物学可接受的惰性载体(例如,固体载体,或液体载体)。
在一种实施方式中,杀虫组合物可以进一步包含至少一种选自以下的添加剂:表面活性剂,稳定剂,催吐剂,崩解剂,消泡剂,润湿剂,分散剂,粘结剂,染料,或填料。
在一些实施方式中,杀虫组合物可以为固体形式。固体形式的非限制性实例可以包括粉末、粉尘或颗粒制剂。
在其它实施方式中,杀虫组合物可以为液体制剂形式。液体形式的实例可以包括但不限于,在适当液体载体中的分散体、悬浮液、乳液或溶液。
在进一步的实施方式中,杀虫组合物可以为液体分散体的形式,其中式I化合物可以分散在水或其它农业适宜的液体载体中。
再在进一步的实施方式中,杀虫组合物可以为在适当有机溶剂中的溶液的形式。在一种实施方式中,广泛用于农业化学的喷雾油可以用作杀虫组合物的有机溶剂。
杀虫组合物可以与一种或多种具有杀螨、杀藻、杀害鸟、杀菌、杀真菌、除草、杀昆虫、杀软体动物、杀线虫、杀啮齿动物、和/或杀病毒性质的化合物联用(例如,在组合的混合物中,或同时或顺序施用)。
此外,杀虫组合物可以与一种或者多种作为抗饲育剂、驱鸟剂、化学绝育剂、除草剂安全剂、昆虫引诱剂、昆虫驱避剂、哺乳动物驱避剂、交配扰乱剂、植物活化剂、植物生长调节剂、和/或协同剂的化合物联用(例如,在组合的混合物中,或同时或顺序施用)。
杀昆虫剂
可以与式I化合物组合使用的杀昆虫剂的非限制性实例可以包括1,2-二氯丙烷(1,2-dichloropropane)、阿维菌素(abamectin)、高灭磷(acephate)、吡虫清(acetamiprid)、家蝇磷(acethion)、乙酰虫腈(acetoprole)、氟酯菊酯(acrinathrin)、丙烯腈(acrylonitrile)、棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、艾氏剂(aldrin)、丙烯除虫菊(allethrin)、阿洛氨菌素(allosamidin)、除害威(allyxycarb)、α-氯氰菊酯(alpha-cypermethrin)、α-蜕皮素(alpha-ecdysone)、α/p/ω-硫丹(α/p/ω-endosulfan)、赛果(amidithion)、灭害威(aminocarb)、胺吸磷(amiton)、草酸胺吸磷(amitonoxalate)、虫螨脒(amitraz)、新烟碱(anabasine)、艾噻达松(athidathion)、艾扎丁(azadirachtin)、唑啶磷(azamethiphos)、益棉磷(azinphos-ethyl)、保棉磷(azinphos-methyl)、偶氮磷(azothoate)、六氟硅酸钡(bariumhexafluorosilicate)、熏虫菊(barthrin)、唑虫威(bendiocarb)、丙硫克拜威(benfuracarb)、杀虫磺(bensultap)、β-氟氯氰菊酯(beta-cyfluthrin)、ξ-氯氰菊酯(zeta-cypermethrin)、联苯菊酯(bifenthrin)、反式丙烯除虫菊(bioallethrin)、bioethanomethrin、生物氯菊酯(biopermethrin)、双二氟虫脲(bistrifluron)、硼砂(borax)、硼酸(boricacid)、溴苯烯磷(bromfenvinfos)、溴烯杀(bromocyclen)、溴-DDT、溴硫磷(bromophos)、乙基溴硫磷(bromophos-ethyl)、合杀威(bufencarb)、噻嗪酮(buprofezin)、畜虫威(butacarb)、特嘧硫磷(butathiofos)、丁叉威(butocarboxim)、丁酯磷(butonate)、氧丁叉威(butoxycarboxim)、硫线磷(cadusafos)、砷酸钙(calciumarsenate)、石硫合剂(calciumpolysulfide)、毒杀芬(camphechlor)、氯灭杀威(carbanolate)、甲萘威(carbaryl)、虫螨威(carbofuran)、二硫化碳(carbondisulfide)、四氯化碳(carbontetrachloride)、三硫磷(carbophenothion)、丁硫克百威(carbosulfan)、巴丹(cartap)、盐酸巴丹(cartaphydrochloride)、氯虫酰胺(chlorantraniliprole)、冰片丹(chlorbicyclen)、氯丹(chlordane)、开蓬(chlordecone)、氯苯脒(chlordimeform)、盐酸氯苯脒(chlordimeformhydrochloride)、壤土氯磷(chlorethoxyfos)、氟唑虫清(chlorfenapyr)、毒虫畏(chlorfenvinphos)、定虫隆(chlorfluazuron)、氯甲磷(chlormephos)、氯仿(chloroform)、氯化苦(chloropicrin)、氯腈肟磷(chlorphoxim)、氯吡唑磷(chlorprazophos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、氯甲硫磷(chlorthiophos)、环虫酰胺(chromafenozide)、瓜菊酯I(cinerinI)、瓜菊酯I(cinerinII)、瓜菊酯(cinerins)、左旋反灭虫菊酯(cismethrin)、除线威(cloethocarb)、氯氰碘柳胺(closantel)、噻虫胺(clothianidin)、乙酰亚砷酸铜(copperacetoarsenite)、砷酸铜(copperarsenate)、环烷酸铜(coppernaphthenate)、油酸铜(copperoleate)、库马磷(coumaphos)、畜虫磷(coumithoate)、克罗米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、氟铝酸钠(cryolite)、苯腈磷(cyanofenphos)、杀螟磷(cyanophos)、果虫磷(cyanthoate)、氰虫酰胺(cyantraniliprole)、环戊烯菊酯(cyclethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、氯氰菊酯(cypermethrin)、苯醚氰菊酯(cyphenothrin)、灭蝇胺(cyromazine)、赛灭磷(cythioate)、DDT、一甲呋喃丹(decarbofuran)、溴氰菊酯(deltamethrin)、田乐磷(demephion)、田乐磷-O(demephion-O)、田乐磷-S(demephion-S)、内吸磷(demeton)、甲基内吸磷(demeton-methyl)、内吸磷-O(demeton-O)、内吸磷-O-甲基(demeton-O-methyl)、内吸磷-S(demeton-S)、内吸磷-S-甲基(demeton-S-methyl)、内吸磷-S-甲基硫(demeton-S-methylsulphon)、杀螨硫隆(diafenthiuron)、氯亚磷(dialifos)、硅藻土(diatomaceousearth)、二嗪农(diazinon)、异氯硫磷(dicapthon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)、N-(3-甲基苯基)氨基甲酸甲酯(dicresyl)、百治磷(dicrotophos)、环虫腈(dicyclanil)、狄氏剂(dieldrin)、氟脲杀(diflubenzuron)、丙羟茶碱(dilor)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、地麦威(dimetan)、乐果(dimethoate)、苄菊酯(dimethrin)、甲基毒虫畏(dimethylvinphos)、敌蝇威(dimetilan)、消螨酚(dinex)、dinex-diclexine、丙硝酚(dinoprop)、戊硝酚(dinosam)、呋虫胺(dinotefuran)、噁茂醚(diofenolan)、杀抗松(dioxabenzofos)、二氧威(dioxacarb)、敌噁磷(dioxathion)、乙拌磷(disulfoton)、噻喃磷(dithicrofos)、右旋柠檬烯(d-limonene)、二硝甲酚(DNOC)、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、多拉克汀(doramectin)、促蜕皮甾酮(ecdysterone)、甲氨基阿维菌素(emamectin)、苯甲酸甲氨基阿维菌素(emamectinbenzoate)、多杀威(EMPC)、烯炔菊酯(empenthrin)、硫丹(endosulfan)、因毒磷(endothion)、异狄氏剂(endrin)、苯硫磷(EPN)、保幼醚(epofenonane)、爱普瑞菌素(eprinomectin)、Es-生物烯丙菊酯(esdépalléthrine)、高氰戊菊酯(esfenvalerate)、etaphos、苯虫威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、益果(ethoate-methyl)、灭克磷(ethoprophos)、甲酸乙酯(ethylformate)、乙基-DDD、1,2-二溴乙烷(ethylenedibromide)、1,2-二氯乙烷(ethylenedichloride)、环氧乙烷(ethyleneoxide)、醚菊酯(etofenprox)、乙嘧硫磷(etrimfos)、EXD、氨磺磷(famphur)、克线磷(fenamiphos)、抗螨唑(fenazaflor)、皮蝇磷(fenchlorphos)、乙苯威(fenethacarb)、五氟苯菊酯(fenfluthrin)、杀螟硫磷(fenitrothion)、丁苯威(fenobucarb)、fenoxacrim、双氧威(fenoxycarb)、吡氯氰菊酯(fenpirithrin)、甲氰菊酯(fenpropathrin)、丰索磷(fensulfothion)、倍硫磷(fenthion)、倍硫磷-乙基(fenthion-ethyl)、氰戊菊酯(fenvalerate)、锐劲特(fipronil)、氟啶虫酰胺(flonicamid)、氟虫酰胺(flubendiamide)(其另外的拆分异构体)、氟氯双苯隆(flucofuron)、氟螨脲(flucycloxuron)、氟氰菊酯(flucythrinate)、嘧虫胺(flufenerim)、氟虫脲(flufenoxuron)、氟丙苄醚(flufenprox)、flufiprole、氟胺氰菊酯(fluvalinate)、地虫磷(fonofos)、伐虫脒(formetanate)、盐酸伐虫脒(formetanatehydrochloride)、安果(formothion)、胺甲威(formparanate)、盐酸胺甲威(formparanatehydrochloride)、丁苯硫磷(fosmethilan)、甲基毒死蜱(fospirate)、伐线丹(fosthietan)、呋喃虫酰肼(fufenozide)、呋线威(furathiocarb)、糠醛菊酯(furethrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、γ-HCH、卤醚菊酯(halfenprox)、特丁苯酰肼(halofenozide)、HCH、HEOD、七氯(heptachlor)、庚虫磷(heptenophos)、速杀硫磷(heterophos)、氟铃脲(hexaflumuron)、艾氏剂(HHDN)、灭蚁腙(hydramethylnon)、氰化氢(hydrogencyanide)、蒙五一二(hydroprene)、喹啉威(hyquincarb)、吡虫啉(imidacloprid)、咪炔菊酯(imiprothrin)、茚虫威(indoxacarb)、碘甲烷(iodomethane)、丰丙磷(IPSP)、氯唑磷(isazofos)、碳氯灵(isobenzan)、水胺硫磷(isocarbophos)、异艾氏剂(isodrin)、丙胺磷(isofenphos)、丙胺磷-甲基(isofenphos-methyl)、异丙威(isoprocarb)、稻瘟灵(isoprothiolane)、叶蚜磷(isothioate)、噁唑磷(isoxathion)、齐墩螨素(ivermectin)、茉莉菊酯I(jasmolinI)、茉莉菊酯II(jasmolinII)、碘硫磷(jodfenphos)、保幼激素I(juvenilehormoneI)、保幼激素II(juvenilehormoneII)、保幼激素III(juvenilehormoneIII)、克来范(kelevan)、蒙七七七(kinoprene)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、砷酸铅(leadarsenate)、lepimectin、溴苯磷(leptophos)、林丹(lindane)、啶虫磷(lirimfos)、氟丙氧脲(lufenuron)、噻唑磷(lythidathion)、马拉硫磷(malathion)、苄丙二腈(malonoben)、叠氮磷(mazidox)、灭蚜磷(mecarbam)、甲基灭蚜磷(mecarphon)、灭蚜松(menazon)、氯氟醚菊酯(meperfluthrin)、二噻磷(mephosfolan)、氯化亚汞(mercurouschloride)、甲亚砜磷(mesulfenfos)、氰氟虫腙(metaflumizone)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、灭虫威(methiocarb)、丁烯胺磷(methocrotophos)、灭多虫(methomyl)、蒙五一五(methoprene)、甲醚菊酯(methothrin)、甲氧滴滴涕(emthoxychlor)、甲氧苯酰肼(methoxyfenozide)、溴甲烷(methylbromide)、异硫氰酸甲酯(methylisothiocyanate)、甲基氯仿(methylchloroform)、二氯甲烷(methylenechloride)、氧卞氟菊酯(metofluthrin)、速灭威(metolcarb)、噁虫酮(metoxadiazone)、速灭磷(mevinphos)、自克威(mexacarbate)、米尔螨素(milbemectin)、米尔贝肟(milbemycinoxime)、丙胺氟磷(mipafox)、灭蚁灵(mirex)、molosultap、久效磷(monocrotophos)、杀虫单(monomehypo)、杀虫单(monosultap)、茂果(morphothion)、莫西克丁(moxidectin)、萘肽磷(naftalofos)、二溴磷(naled)、萘(naphthalene)、烟碱(nicotine)、氟蚁灵(nifluridide)、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、腈叉威(nitrilacarb)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氧乐果(omethoate)、甲氨叉威(oxamyl)、砜吸磷(oxydemeton-methyl)、异砜磷(oxydeprofos)、砜拌磷(oxydisulfoton)、对-二氯苯(para-dichlorobenzene)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、氟幼脲(penfluron)、五氯酚(pentachlorophenol)、苄氯菊脂(permethrin)、芬硫磷(phenkapton)、苯醚菊酯(phenothrin)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、棉安磷(phosfolan)、亚胺硫磷(phosmet)、对氯硫磷(phosnichlor)、磷胺(phosphamidon)、磷化氢(phosphine)、肟硫磷(phoxim)、甲基肟硫磷(phoxim-methyl)、甲胺嘧磷(pirimetaphos)、抗蚜威(pirimicarb)、乙基虫螨磷(pirimiphos-ethyl)、甲基虫螨磷(pirimiphos-methyl)、亚砷酸钾(potassiumarsenite)、硫氰酸钾(potassiumthiocyanate)、pp'-DDT、炔酮菊酯(prallethrin)、早熟素I(precoceneI)、早熟素II(precoceneII)、早熟素III(precoceneIII)、酰胺嘧啶啉(primidophos)、丙溴磷(profenofos)、环丙氟灵(profluralin)、profluthrin、蜱虱威(promacyl)、猛杀威(promecarb)、丙虫磷(propaphos)、烯虫磷(propetamphos)、残杀威(propoxur)、乙噻唑磷(prothidathion)、丙硫磷(prothiofos)、发果(prothoate)、protrifenbute、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclofos)、嘧啶威(pyrafluprole)、吡菌磷(pyrazophos)、反灭虫菊(pyresmethrin)、除虫菊酯I(pyrethrinI)、除虫菊酯II(pyrethrinII)、除虫菊(pyrethrins)、哒螨酮(pyridaben)、啶虫丙醚(pyridalyl)、打杀磷(pyridaphenthion)、pyrifluquinazon、嘧胺苯醚(pyrimidifen)、嘧啶磷(pyrimitate)、吡啶醇(pyriprole)、蚊蝇醚(pyriproxyfen)、苦木(quassia)、喹噁啉(quinalphos)、甲基喹噁啉(quinalphos-methyl)、喹塞昂(quinothion)、碘醚柳胺(rafoxanide)、苄呋菊酯(resmethrin)、鱼藤酮(rotenone)、鱼泥汀(ryania)、沙巴草(sabadilla)、八甲磷(schradan)、赛拉菌素(selamectin)、灭虫硅醚(silafluofen)、硅胶(silicagel)、亚砷酸钠(sodiumarsenite)、氟化钠(sodiumfluoride)、六氟硅酸钠(sodiumhexafluorosilicate)、硫氰酸钠(sodiumthiocyanate)、苏果(sophamide)、多虫菌素(spinetoram)、艾克敌(spinosad)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、磺苯醚隆(sulcofuron)、磺苯醚隆钠(sulcofuron-sodium)、氟虫胺(sulfluramid)、硫特普(sulfotep)、氟啶虫胺腈(sulfoxaflor)、氟化硫(sulfurylfluoride)、乙丙硫磷(sulprofos)、τ-氟胺氰菊酯(tau-fluvalinate)、噻螨威(tazimcarb)、滴滴滴(TDE)、双苯酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、嘧丙磷(tebupirimfos)、伏虫隆(teflubenzuron)、七氟菊酯(tefluthrin)、双硫磷(temephos)、特普(TEPP)、环戊烯丙菊酯(terallethrin)、特丁磷(terbufos)、四氯乙烷(tetrachloroethane)、杀虫畏(tetrachlorvinphos)、胺菊酯(tetramethrin)、tetramethylfluthrin、θ-氯氰菊酯(theta-cypermethrin)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、噻氯磷(thicrofos)、抗虫威(thiocarboxime)、硫环杀(thiocyclam)、草酸硫环杀(thiocyclamoxalate)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、甲基乙拌磷(thiometon)、杀虫双(thiosultap)、杀虫双-二钠(thiosultap-disodium)、杀虫双-单钠(thiosultap-monosodium)、敌贝特(thuringiensin)、唑虫酰胺(tolfenpyrad)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、反氯菊酯(transpermethrin)、苯螨噻(triarathene)、醚苯磺隆(triazamate)、三唑磷(triazophos)、敌百虫(trichlorfon)、异皮蝇磷(trichlormetaphos-3)、壤虫磷(trichloronat)、氯苯乙丙磷(trifenofos)、杀虫隆(triflumuron)、混杀威(trimethacarb)、硫烯酸酯(triprene)、蚜灭多(vamidothion)、氟吡唑虫(vaniliprole)、二甲威(XMC)、灭杀威(xylylcarb)、ζ-氯氰菊酯(zeta-cypermethrin)、或zolaprofos。
杀螨虫剂
可以与式I化合物组合使用的杀螨剂的非限制性实例可以包括:灭螨醌(acequinocyl)、amidoflumet、三氧化二砷(arsenousoxide)、偶氮苯(azobenzene)、唑环锡(azocyclotin)、苯菌灵(benomyl)、苯噁磷(benoxafos)、苯螨特(benzoximate)、苯甲酸苄酯(benzylbenzoate)、联苯肼酯(bifenazate)、乐杀螨(binapacryl)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、氯杀螨(chlorbenside)、杀螨醇(chlorfenethol)、杀螨酯(chlorfenson)、敌螨丹(chlorfensulphide)、乙酯杀螨醇(chlorobenzilate)、伊托明(chloromebuform)、螟铃畏(chloromethiuron)、丙酯杀螨醇(chloropropylate)、四螨嗪(clofentezine)、cyenopyrafen、丁氟螨酯(cyflumetofen)、三环锡(cyhexatin)、苯氟磺胺(dichlofluanid)、开乐散(dicofol)、除螨灵(dienochlor)、氟螨嗪(diflovidazin)、消螨通(dinobuton)、敌螨普(dinocap)、敌螨普-4(dinocap-4)、敌螨普-6(dinocap6)、敌螨通(dinocton)、硝戊酯(dinopenton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、二苯砜(diphenylsulfone)、双硫仑(disulfiram)、苯氧炔螨(dofenapyn)、特苯噁唑(etoxazole)、喹螨醚(fenazaquin)、杀螨锡(fenbutatinoxide)、苯硫威(fenothiocarb)、唑螨酯(fenpyroximate)、除螨酯(fenson)、氟硝二苯胺(fentrifanil)、嘧螨酯(fluacrypyrim)、氟佐隆(fluazuron)、噻唑螨(flubenzimine)、联氟螨(fluenetil)、氟氯苯菊酯(flumethrin)、氟杀螨(fluorbenside)、噻螨酮(hexythiazox)、灭芥(mesulfen)、MNAF、华光霉素(nikkomycins)、灭螨醇(proclonol)、克螨特(propargite)、quintiofos、螺螨酯(spirodiclofen)、舒非仑(sulfiram)、硫黄(sulfur)、三氯杀螨砜(tetradifon)、杀螨霉素(tetranactin)、杀螨好(tetrasul)或克杀螨(thioquinox)。
杀线虫剂
可以与式I化合物组合使用的杀线虫剂可以包括1,3-二氯丙烯(1,3-dichloropropene)、benclothiaz、棉隆(dazomet)、棉隆钠(dazomet-sodium)、DBCP、DCIP、除线特(diamidafos)、fluensulfone、噻唑酮磷(fosthiazate)、糠醛(furfural)、新烟碱类(imicyafos)、isamidofos、氯唑磷(isazofos)、威百亩(metam)、安百亩(metam-ammonium)、metam-potassium、威百亩(metam-sodium)、乙丙磷威(phosphocarb)或硫磷嗪(thionazin)。
杀真菌剂
可以与式I化合物组合使用的杀真菌剂可以包括(3-乙氧基丙基)溴化汞((3-ethoxypropyl)mercurybromide)、氯化2-甲氧基乙基汞(2-methoxyethylmercurychloride)、2-苯基-苯酚(2-phenylphenol)、8-羟基喹啉硫酸盐(8-hydroxyquinolinesulfate)、8-苯基汞基氧基喹啉(8-phenylmercurioxyquinoline)、acibenzolar、活化酯(acibenzolar-S-methyl)、acypetacs、acypetacs-copper、acypetacs-zinc、烯丙菊酯(aldimorph)、烯丙醇、辛唑嘧菌胺(ametoctradin)、双甲脒(amisulbrom)、氨丙膦酸(ampropylfos)、敌菌灵(anilazine)、aureofungin、阿扎康唑(azaconazole)、氧化福美双(azithiram)、腈嘧菌酯(azoxystrobin)、多硫化钡(bariumpolysulfide)、苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、醌肟腙(benquinox)、丙唑草隆(bentaluron)、苯噻菌胺(benthiavalicarb)、苯噻菌胺酯(benthiavalicarb-isopropyl)、苯扎氯铵(benzalkoniumchloride)、苄烯酸(benzamacril)、苄烯酸异丁酯(benzamacril-isobutyl)、苯杂吗(benzamorf)、苯基异羟肟酸(benzohydroxamicacid)、bethoxazin、乐杀螨(binapacryl)、联苯(biphenyl)、联苯三唑醇(bitertanol)、硫双二氯酚(bithionol)、bixafen、灭瘟素(blasticidin-S)、波尔多液(BordeauxMixture)、烟酰胺(boscalid)、糠菌唑(bromuconazole)、乙嘧酚磺酸酯(bupirimate)、波尔多液(Burgundymixture)、丁硫啶(buthiobate)、丁胺(butylamine)、石硫合剂(calciumpolysulfide)、敌菌丹(captafol)、克菌丹(captan)、吗菌威(carbamorph)、多菌灵(carbendazim)、萎锈灵(carboxin)、环丙酰菌胺(carpropamid)、香芹酮(carvone)、切欣特液(Cheshuntmixture)、灭螨猛(chinomethionat)、灭瘟唑(chlobenthiazone)、双胺灵(chloraniformethan)、氯醌(chloranil)、苯咪唑菌(chlorfenazole)、氯二硝基萘(chlorodinitronaphthalene)、地茂散(chloroneb)、氯化苦(chloropicrin)、百菌清(chlorothalonil)、四氯喹噁啉(chlorquinox)、乙菌利(chlozolinate)、咪菌酮(climbazole)、克霉唑(clotrimazole)、乙酸铜(copperacetate)、碱式碳酸铜(coppercarbonatebasic)、氢氧化铜(copperhydroxide)、环烷酸铜(coppernaphthenate)、油酸铜(copperoleate)、碱式氯化铜(copperoxychloride)、硅酸铜(coppersilicate)、硫酸铜(coppersulfate)、铬酸铜锌(copperzincchromate)、甲酚(cresol)、硫杂灵(cufraneb)、福美铜氯(cuprobam)、氧化亚铜(cuprousoxide)、氰霜唑(cyazofamid)、环糠酰胺(cyclafuramid)、放线菌胺(cycloheximide)、环氟苄酰胺(cyflufenamid)、霜脲氰(cymoxanil)、氰菌灵(cypendazole)、环菌唑(cyproconazole)、嘧菌环胺(cyprodinil)、棉隆(dazomet)、棉隆-钠(dazomet-sodium)、二溴氯丙烷(DBCP)、咪菌威(debacarb)、癸磷锡(decafentin)、脱氢乙酸(dehydroaceticacid)、苯氟磺胺(dichlofluanid)、二氯萘醌(dichlone)、双氯酚(dichlorophen)、菌核利(dichlozoline)、苄氯三唑醇(diclobutrazol)、双氯氰菌胺(diclocymet)、哒菌酮(diclomezine)、哒菌酮-钠(diclomezine-sodium)、dicloran、乙霉威(diethofencarb)、焦碳酸二乙酯(diethylpyrocarbonate)、苯醚甲环唑(difenoconazole)、氟嘧菌胺(diflumetorim)、甲菌定(dimethirimol)、烯酰吗啉(dimethomorph)、醚菌胺(dimoxystrobin)、烯唑醇(diniconazole)、精烯唑醇(diniconazole-M)、消螨通(dinobuton)、二硝巴豆酸酯(dinocap)、二硝巴豆酸酯-4(dinocap-4)、二硝巴豆酸酯-6(dinocap-6)、敌螨通(dinocton)、硝戊酯(dinopenton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、二苯基胺(diphenylamine)、吡菌硫(dipyrithione)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、二硝甲酚、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、十二环吗啉(dodemorph)、十二环吗啉乙酸盐(dodemorphacetate)、十二环吗啉苯甲酸盐(dodemorphbenzoate)、多敌菌(dodicin)、多敌菌-钠(dodicin-钠)、多果定(dodine)、敌菌酮(drazoxolon)、敌瘟磷(edifenphos)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、代森硫(etem)、噻唑菌胺(ethaboxam)、乙嘧酚(ethirimol)、乙氧喹啉(ethoxyquin)、2,3-二羟基丙基硫醇乙基汞(ethylmercury2,3-dihydroxypropylmercaptide)、乙酸乙基汞(ethylmercuryacetate)、溴乙基汞(ethylmercurybromide)、氯乙基汞(ethylmercurychloride)、磷酸乙基汞(ethylmercuryphosphate)、土菌灵(etridiazole)、噁唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、敌磺钠(fenaminosulf)、咪菌腈(fenapanil)、氯苯嘧啶醇(fenarimol)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、环酰菌胺(fenhexamid)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、拌种咯(fenpiclonil)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、三苯锡(fentin)、三苯基氯化锡(fentinchloride)、三苯基氢氧化锡(fentinhydroxide)、福美铁(ferbam)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、咯菌腈(fludioxonil)、氟酰菌胺(flumetover)、氟吗啉(flumorph)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、氟氯菌核利(fluoroimide)、三氟苯唑(fluotrimazole)、氟嘧菌酯(fluoxastrobin)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟噻菌净(flutianil)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、fluxapyroxad、灭菌丹(folpet)、甲醛(formaldehyde)、三乙膦酸(fosetyl)、三乙膦酸铝(fosetyl-aluminium)、麦穗宁(fuberidazole)、呋霜灵(furalaxyl)、呋吡菌胺(furametpyr)、灭菌胺(furcarbanil)、呋菌唑(furconazole)、顺式呋菌唑(furconazole-cis)、糠醛(furfural)、拌种胺(furmecyclox)、呋菌隆(furophanate)、果绿啶(glyodine)、灰黄霉素(griseofulvin)、双胍辛乙酸盐(guazatine)、丙烯酸喹啉酯(halacrinate)、六氯苯(hexachlorobenzene)、瘤氯丁二烯(hexachlorobutadiene)、己唑醇(hexaconazole)、环己硫磷(hexylthiofos)、萘磺汞(hydrargaphen)、噁霉灵(hymexazol)、抑霉唑(imazalil)、硝酸抑霉唑(imazalilnitrate)、硫酸抑霉唑(imazalilsulfate)、亚胺唑(imibenconazole)、双胍辛胺(iminoctadine)、三乙酸双胍辛胺(iminoctadinetriacetate)、双胍辛胺三(对十二烷基苯磺酸盐)[iminoctadinetris(albesilate)]、碘甲烷(iodomethane)、种菌唑(ipconazole)、异稻瘟净(iprobenfos)、异菌脲(iprodione)、缬霉威(iprovalicarb)、稻瘟灵(isoprothiolane)、吡唑萘菌胺(isopyrazam)、异噻菌胺(isotianil)、氯苯咪菌酮(isovaledione)、春雷霉素(kasugamycin)、醚菌甲酯(kresoxim-methyl)、代森锰铜(mancopper)、代森锰锌(mancozeb)、双炔酰菌胺(mandipropamid)、代森锰(maneb)、邻酰胺(mebenil)、咪卡病西(mecarbinzid)、嘧菌胺(mepanipyrim)、灭锈胺(mepronil)、二硝巴豆酸酯(meptyldinocap)、氯化汞(mercuricchloride)、氧化汞(mercuricoxide)、氯化亚汞(mercurouschloride)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、威百亩(metam)、安百亩(metam-ammonium)、metam-potassium、威百亩(metam-sodium)、肼叉噁唑酮(metazoxolon)、叶菌唑(metconazole)、磺菌威(methasulfocarb)、呋菌胺(methfuroxam)、溴甲烷(methylbromide)、异硫氰酸甲酯、苯甲酸甲基汞(methylmercurybenzoate)、氰胍甲汞(methylmercurydicyandiamide)、五氯苯酚甲基汞(methylmercurypentachlorophenoxide)、代森联(metiram)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、噻菌胺(metsulfovax)、代森环(milneb)、腈菌唑(myclobutanil)、甲菌利(myclozolin)、N-(乙基汞基)-对-甲苯磺酰苯胺(N-(ethylmercury)-p-toluenesulphonanilide)、代森钠(nabam)、多马霉素(natamycin)、硫氰散(nitrostyrene)、酞菌异丙酯(nitrothal-isopropyl)、氟苯嘧啶醇(nuarimol)、八氯酮(OCH)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、噁霜灵(oxadixyl)、喹啉铜(oxine-copper)、噁咪唑(oxpoconazole)、富马酸噁咪唑(oxpoconazolefumarate)、氧化萎锈灵(oxycarboxin)、稻瘟酯(pefurazoate)、戊菌唑(penconazole)、戊菌隆(pencycuron)、戊苯吡菌胺(penflufen)、五氯酚(pentachlorophenol)、吡噻菌胺(penthiopyrad)、苯基汞脲(phenylmercuriurea)、乙酸苯汞(phenylmercuryacetate)、氯化苯汞(phenylmercurychloride)、儿茶酚的苯汞衍生物(phenylmercuryderivativeofpyrocatechol)、硝酸苯汞(phenylmercurynitrate)、水杨酸苯汞(phenylmercurysalicylate)、氯瘟磷(phosdiphen)、四氯苯酞(phthalide)、啶氧菌酯(picoxystrobin)、病花灵(piperalin)、聚氨基甲酸酯(polycarbamate)、多抗霉素(polyoxin)、多氧霉素(polyoxorim)、多氧霉素-锌(polyoxorim-zinc)、叠氮化钾(potassiumazide)、多硫化钾(potassiumpolysulfide)、硫氰酸钾(potassiumthiocyanate)、烯丙苯噻唑(probenazole)、咪鲜胺(prochloraz)、腐霉利(procymidone)、霜霉威(propamocarb)、盐酸霜霉威(propamocarbhydrochloride)、丙环唑(propiconazole)、丙森锌(propineb)、丙氧喹啉(proquinazid)、硫菌威(prothiocarb)、盐酸硫菌威(prothiocarbhydrochloride)、丙硫菌唑(prothioconazole)、吡喃灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、吡唑醚菌酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、定菌磷(pyrazophos)、pyribencarb、啶菌腈(pyridinitril)、啶斑肟(pyrifenox)、嘧霉胺(pyrimethanil)、pyriofenone、咯喹酮(pyroquilon)、吡氧氯(pyroxychlor)、氯吡呋醚(pyroxyfur)、5-乙酰基-8-羟基喹啉(quinacetol)、5-乙酰基-8-羟基喹啉硫酸盐(quinacetolsulfate)、酯菌腙(quinazamid)、喹唑菌酮(quinconazole)、苯氧喹啉(quinoxyfen)、五氯硝基苯(quintozene)、吡咪唑菌(rabenzazole)、水杨酰胺(salicylanilide)、环丙吡菌胺(sedaxane)、硅噻菌胺(silthiofam)、硅氟唑(simeconazole)、叠氮化钠(sodiumazide)、邻苯基苯酚钠(sodiumorthophenylphenoxide)、五氯苯酚钠(sodiumpentachlorophenoxide)、多硫化钠(sodiumpolysulfide)、螺环菌胺(spiroxamine)、链霉素(streptomycin)、硫磺(sulfur)、戊苯砜(sultropen)、TCMTB、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、福代硫(tecoram)、四氟醚唑(tetraconazole)、噻菌灵(thiabendazole)、噻二氟(thiadifluor)、噻菌腈(thicyofen)、噻氟菌胺(thifluzamide)、苯菌胺(thiochlorfenphim)、硫柳汞(thiomersal)、硫菌灵(thiophanate)、甲基硫菌灵(thiophanate-methyl)、克杀螨(thioquinox)、福美双(thiram)、噻酰菌胺(tiadinil)、硫氰苯甲酰胺(tioxymid)、甲基立枯磷(tolclofos-methyl)、甲苯氟磺胺(tolylfluanid)、乙酸甲苯汞(tolylmercuryacetate)、三唑酮(triadimefon)、三唑醇(triadimenol)、三唑磷胺(triamiphos)、嘧菌醇(triarimol)、叶锈特(triazbutil)、咪唑嗪(triazoxide)、氧化三丁基锡(tributyltinoxide)、水杨菌胺(trichlamide)、三环唑(tricyclazole)、十三吗啉(tridemorph)、肟菌酯(trifloxystrobin)、氟菌唑(triflumizole)、嗪氨灵(triforine)、灭菌唑(triticonazole)、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、井冈霉素(validamycin)、valifenalate、乙烯菌核利(vinclozolin)、灭杀威(zarilamid)、环烷酸锌(zincnaphthenate)、代森锌(zineb)、福美锌(ziram)或苯酰菌胺(zoxamide)。
除草剂
可以与式I化合物组合使用的除草剂的非限制性实例可以包括:草芽平(2,3,6-TBA)、2,3,6-TBA-二甲基铵、2,3,6-TBA-钠、2,4,5-T、2,4,5-T-2-丁氧基丙基、2,4,5-T-2-乙基己基、2,4,5-T-3-丁氧基丙基、2,4,5-TB、2,4,5-T-丁氧基异丙基(2,4,5-T-butometyl)、2,4,5-T-丁氧基乙基、2,4,5-T-丁基、2,4,5-T-异丁基、2,4,5-T-异辛基、2,4,5-T-异丙基、2,4,5-T-甲基、2,4,5-T-戊基、2,4,5-T-钠、2,4,5-T-三乙基铵、2,4,5-T-三乙醇胺、2,4-D、2,4-D-2-丁氧基丙基、2,4-D-2-乙基己基、2,4-D-3-丁氧基丙基、2,4-D-铵、2,4-DB、2,4-DB-丁基、2,4-DB-二甲基铵、2,4-DB-异辛基、2,4-DB-钾、2,4-DB-钠、2,4-D-丁氧基乙基、2,4-D-丁基、2,4-D-二乙基铵、2,4-D-二甲基铵、2,4-D-二乙醇胺、2,4-D-十二烷基铵、2,4-DEB、2,4-DEP、2,4-D-乙基、2,4-D-庚基铵、2,4-D-异丁基、2,4-D-异辛基、2,4-D-异丙基、2,4-D-异丙基铵、2,4-D-锂、2,4-D-甲基庚基、2,4-D-甲基、2,4-D-辛基、2,4-D-戊基、2,4-D-钾、2,4-D-丙基、2,4-D-钠、2,4-D-四氢呋喃基、2,4-D-四癸基铵、2,4-D-三乙基铵、2,4-D-三(2-羟基丙基)铵、2,4-D-三乙醇胺、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、刈草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚-甲基(acifluorfen-methyl)、三氟羧草醚-钠(acifluorfen-sodium)、苯草醚(aclonifen)、丙烯醛(acrolein)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、禾草灭-钠、烯丙醇、五氯戊酮酸(alorac)、特津酮(ametridione)、莠灭净(ametryn)、特草嗪酮(amibuzin)、氨唑草酮(amicarbazone)、磺氨磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸-甲基、环丙嘧啶酸-钾、氯氨基吡啶酸(aminopyralid)、氯氨基吡啶酸-钾、氯氨基吡啶酸-三(2-羟基丙基)铵、甲基胺草磷(amiprofos-methyl)、杀草强(amitrole)、氨基磺酸铵(ammoniumsulfamate)、莎稗磷(anilofos)、疏草隆(anisuron)、磺草灵(asulam)、磺草灵-钾、磺草灵-钠、莠去通(atraton)、莠去津(atrazine)、唑啶炔草(azafenidin)、四唑磺隆(azimsulfuron)、叠氮净(aziprotryne)、燕麦灵(barban)、BCPC、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵-二甲基铵、草除灵-乙基、草除灵-钾、bencarbazone、氟草胺(benfluralin)、呋草磺(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆-甲基、地散磷(bensulide)、噻草平(bentazone)、噻草平-钠、胺酸杀(benzadox)、胺酸杀-铵、双苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、新燕灵-乙基、噻草隆(benzthiazuron)、bicyclopyrone、治草醚(bifenox)、双丙氨酰膦(bilanafos)、双丙氨酰膦-钠、双嘧苯甲酸(bispyribac)、双嘧苯甲酸-钠、硼砂(borax)、除草定(bromacil)、除草定-锂(bromacil-lithium)、除草定-钠、糠草腈(bromobonil)、溴丁酰草胺(bromobutide)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)、丁酸溴苯腈(bromoxynilbutyrate)、庚酸溴苯腈(bromoxynilheptanoate)、辛酸溴苯腈(bromoxyniloctanoate)、溴苯腈-钾、杀莠敏(brompyrazon)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草膦(butamifos)、丁烯草胺(butenachlor)、特咪唑草(buthidazole)、丁噻隆(buthiuron)、地乐胺(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、苏达灭(butylate)、二甲胂酸(cacodylicacid)、苯酮唑(cafenstrole)、氯酸钙(calciumchlorate)、氰氨化钙(calciumcyanamide)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、长杀草(carbetamide)、特噁唑威(carboxazole)、氟酮唑草(carfentrazone)、氟酮唑草-乙基、CDEA、CEPC、氯硝醚(chlomethoxyfen)、草灭平(chloramben)、草灭平-铵、草灭平-二乙醇胺、草灭平-甲基、草灭平-甲基铵、草灭平-钠、丁酰草胺(chloranocryl)、炔禾灵(chlorazifop)、炔禾灵-炔丙基(chlorazifop-propargyl)、可乐津(chlorazine)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、乙氧苯隆(chloreturon)、伐草克(chlorfenac)、伐草克-钠、燕麦酯(chlorfenprop)、燕麦酯-甲基、氟嘧杀(chlorflurazole)、氯甲丹(chlorflurenol)、氯甲丹-甲基、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆-乙基、草枯醚(chlornitrofen)、三氯丙酸(chloropon)、氯麦隆(chlorotoluron)、枯草隆(chloroxuron)、羟敌草腈(chloroxynil)、草败死(chlorprocarb)、氯苯胺灵(chlorpropham)、绿磺隆(chlorsulfuron)、氯酞酸(chlorthal)、氯酞酸-二甲基、氯酞酸-单甲基、草克乐(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、咯草隆(cisanilide)、烯草酮(clethodim)、碘氯啶酯(cliodinate)、炔草酯(clodinafop)、炔草酯-炔丙基、氯丁草(clofop)、氯丁草-异丁基、异噁草酮(clomazone)、稗草胺(clomeprop)、调果酸(cloprop)、环丁烯草酮(cloproxydim)、二氯吡啶酸(clopyralid)、二氯吡啶酸-甲基、二氯吡啶酸-乙醇胺、二氯吡啶酸-钾、二氯吡啶酸-三(2-羟基丙基)铵、氯酯磺草胺(cloransulam)、氯酯磺草胺-甲基、CMA、硫酸铜、CPMF、CPPC、醚草敏(credazine)、甲酚(cresol)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草净(cyanatryn)、氰草津(cyanazine)、草灭特(cycloate)、环丙磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、氰氟草酯-丁基、牧草快(cyperquat)、盐酸牧草快(cyperquatchloride)、环丙津(cyprazine)、三环塞草胺(cyprazole)、环酰草胺(cypromid)、香草隆(daimuron)、茅草枯(dalapon)、茅草枯-钙、茅草枯-镁、茅草枯-钠、棉隆(dazomet)、棉隆-钠、敌草乐(delachlor)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-allate)、麦草畏(dicamba)、麦草畏-二甲基铵、麦草畏-二乙醇胺、麦草畏-异丙基铵、麦草畏-甲基、麦草畏-乙醇胺、麦草畏-钾、麦草畏-钠、麦草畏-三醇胺、敌草腈(dichlobenil)、氯全隆(dichloralurea)、苄胺灵(dichlormate)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸-2-乙基己基、2,4-滴丙酸-丁氧基乙基、2,4-滴丙酸-二甲基铵、2,4-滴丙酸-乙基铵、2,4-滴丙酸-异辛基、2,4-滴丙酸-甲基、精2,4-滴丙酸(dichlorprop-P)、精2,4-滴丙酸-二甲基铵、2,4-滴丙酸-钾、2,4-滴丙酸-钠、氯甲草(diclofop)、氯甲草-甲基、唑嘧磺胺(diclosulam)、二乙除草双(diethamquat)、二盐酸二乙除草双(diethamquatdichloride)、安塔(diethatyl)、安塔-乙基、氟苯戊烯酸(difenopenten)、氟苯戊烯酸-乙基、枯莠隆(difenoxuron)、苯敌快(difenzoquat)、甲硫酸苯敌快、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、二氟吡隆-钠、噁唑隆(dimefuron)、哌草丹(dimepiperate)、克草胺(dimethachlor)、戊草津(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、敌灭生(dimexano)、敌米达松(dimidazon)、敌乐胺(dinitramine)、地乐特(dinofenate)、丙硝酚(dinoprop)、戊硝酚(dinosam)、地乐酚(dinoseb)、乙酸地乐酚(dinosebacetate)、地乐酚-铵、地乐酚-二乙醇胺、地乐酚-钠、地乐酚-三乙醇胺、特乐酚(dinoterb)、乙酸特乐酚(dinoterbacetate)、敌鼠-钠(diphacinone-sodium)、草乃敌(diphenamid)、杀草净(dipropetryn)、敌草快(diquat)、敌草快二溴化物(diquatdibromide)、2,4-滴硫酸(disul)、2,4-滴硫钠(disul-sodium)、氟硫草定(dithiopyr)、敌草隆(diuron)、DMPA、二硝甲酚、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、DSMA、EBEP、甘草津(eglinazine)、甘草津-乙基、草藻灭(endothal)、草藻灭-二铵、草藻灭-二钾、草藻灭-二钠、磺唑草(epronaz)、EPTC、抑草蓬(erbon)、禾草畏(esprocarb)、丁氟消草(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆-甲基、噻二唑隆(ethidimuron)、抑草威(ethiolate)、乙呋草磺(ethofumesate)、氯氟草醚(ethoxyfen)、氯氟草醚-乙基、乙氧嘧磺隆(ethoxysulfuron)、硝草酚(etinofen)、乙胺草醚(etnipromid)、乙氧苯酰草(etobenzanid)、EXD、酰苯磺威(fenasulam)、2,4,5-涕丙酸(fenoprop)、2,4,5-涕丙酸-3-丁氧基丙基、2,4,5-涕丙酸-丁氧基异丙基、2,4,5-涕丙酸-丁氧基乙基、2,4,5-涕丙酸-丁基、2,4,5-涕丙酸-异辛基、2,4,5-涕丙酸-甲基、2,4,5-涕丙酸-钾、噁唑禾草灵(fenoxaprop)、噁唑禾草灵-乙基、精噁唑禾草灵(fenoxaprop-P)、精噁唑禾草灵-乙基、fenoxasulfone、氯苯氧乙醇(fenteracol)、噻唑禾草灵(fenthiaprop)、噻唑禾草灵-乙基、四唑草胺(fentrazamide)、非草隆(fenuron)、非草隆TCA、硫酸亚铁(ferroussulfate)、氟燕灵(flamprop)、氟燕灵-异丙基、强氟燕灵(flamprop-M)、氟燕灵-甲基、强氟燕灵-异丙基、强氟燕灵-甲基、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、吡氟禾草灵-丁基、吡氟禾草灵-甲基、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵-丁基、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟酮磺隆-钠、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯-乙基、氟唑啶草(flumetsulam)、三氟噁嗪(flumezin)、氟烯草酸(flumiclorac)、氟烯草酸-戊基、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、伏草隆(fluometuron)、消草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚-乙基、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、氟苯隆(fluothiuron)、氟胺草唑(flupoxam)、flupropacil、四氟丙酸(flupropanate)、四氟丙酸-钠、氟啶磺隆(flupyrsulfuron)、氟啶磺隆-甲基-钠、氟草同(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸-丁氧基异丙酯(fluroxypyr-butometyl)、氯氟吡氧乙酸-异辛酯、呋草酮(flurtamone)、达草氟(fluthiacet)、达草氟-甲基、氟磺胺草醚(fomesafen)、氟磺胺草醚-钠、甲酰胺磺隆(foramsulfuron)、膦铵素(fosamine)、膦铵素-铵、氟呋草醚(furyloxyfen)、草丁膦(glufosinate)、草铵膦(glufosinate-ammonium)、精草丁膦(glufosinate-P)、精草铵膦、精草丁膦-钠、草甘膦(glyphosate)、草甘膦-二铵、草甘膦-二甲基铵、草甘膦-异丙基铵、草甘膦-单铵、草甘膦-钾、草甘膦-一倍半钠、草甘膦-三甲基锍盐(glyphosatetrimesium)、氟硝磺酰胺(halosafen)、吡氯磺隆(halosulfuron)、吡氯磺隆-甲基、卤草定(haloxydine)、氟吡禾灵(haloxyfop)、氟吡禾灵-乙氧基乙基、氟吡禾灵-甲基、精氟吡禾灵(haloxyfop-P)、精氟吡禾灵-乙氧基乙基、精氟吡禾灵-甲基、氟吡禾灵-钠、六氯丙酮(hexachloroacetone)、六氟胂酸盐(hexaflurate)、六嗪酮(hexazinone)、咪草酯(imazamethabenz)、咪草酯-甲基、咪草啶酸(imazamox)、咪草啶酸-铵、甲咪唑烟酸(imazapic)、甲咪唑烟酸-铵、灭草烟(imazapyr)、灭草烟-异丙基铵、灭草喹(imazaquin)、灭草喹-铵、灭草喹-甲基、灭草喹-钠、咪草烟(imazethapyr)、咪草烟-铵、啶咪磺隆(imazosulfuron)、茚草酮(indanofan)、indaziflam、碘草腈(iodobonil)、碘甲烷(iodomethane)、碘磺隆(iodosulfuron)、甲基碘磺隆钠盐、iofensulfuron、碘苯腈(ioxynil)、辛酸碘苯腈(ioxyniloctanoate)、碘苯腈-锂、碘苯腈-钠、抑草津(ipazine)、ipfencarbazone、丙草定(iprymidam)、丁咪胺(isocarbamid)、异草定(isocil)、丁嗪草酮(isomethiozin)、异草完隆(isonoruron)、氮草(isopolinate)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁氟草酮(isoxaflutole)、噁草醚(isoxapyrifop)、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、甲基胂酸(MAA)、甲胂一铵(MAMA)、2甲4氯(MCPA)、2甲4氯-2-乙基己基、2甲4氯-丁氧基乙基、2甲4氯-丁基、2甲4氯-二甲基铵、2甲4氯-二乙醇胺、2甲4氯-乙基、2甲4氯-异丁基、2甲4氯-异辛基、2甲4氯-异丙基、2甲4氯-甲基、2甲4氯-乙醇胺、2甲4氯-钾、2甲4氯-钠、酚硫杀(MCPA-thioethyl)、2甲4氯-三乙醇胺、2甲4氯丁酸(MCPB)、2甲4氯丁酸-乙基、2甲4氯丁酸-甲基、2甲4氯丁酸-钠、2甲4氯丙酸(mecoprop)、2甲4氯丙酸-2-乙基己基、2甲4氯丙酸-二甲基铵、2甲4氯丙酸-二乙醇胺、2甲4氯丙酸-ethadyl、2甲4氯丙酸-异辛基、2甲4氯丙酸-甲基、精2甲4氯丙酸(mecoprop-P)、精2甲4氯丙酸-二甲基铵、精2甲4氯丙酸-异丁基、2甲4氯丙酸-钾、精2甲4氯丙酸-钾、2甲4氯丙酸-钠、2甲4氯丙酸-三乙醇胺、丁硝酚(medinoterb)、乙酸丁硝酚(medinoterbacetate)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、氟磺酰草胺-二乙醇胺、氟磺酰草胺-钾、灭莠津(mesoprazine)、甲基二磺隆(mesosulfuron)、甲基二磺隆-甲基、甲基磺草酮(mesotrione)、威百亩(metam)、威百亩-铵、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、威百亩-钾、威百亩-钠、吡草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、氟哒草(metflurazon)、噻唑隆(methabenzthiazuron)、氟烯硝草(methalpropalin)、灭草定(methazole)、甲硫苯威(methiobencarb)、methiozolin、灭草恒(methiuron)、醚草通(methometon)、盖草津(methoprotryne)、溴甲烷(methylbromide)、异硫氰酸甲酯、苯丙隆(methyldymron)、色满隆(metobenzuron)、异丙甲草胺(metolachlor)、唑草磺胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆-甲基、草达灭(molinate)、庚酰草胺(monalide)、特噁唑隆(monisouron)、单氯代乙酸(monochloroaceticacid)、绿谷隆(monolinuron)、灭草隆(monuron)、灭草隆TCA、伐草快(morfamquat)、伐草快二氯化物(morfamquatdichloride)、甲胂一钠(MSMA)、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、萘草胺-钠、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、吡氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、达草灭(norflurazon)、草完隆(noruron)、八氯酮(OCH)、坪草丹(orbencarb)、邻-二氯苯(ortho-dichlorobenzene)、orthosulfamuron、黄草消(oryzalin)、炔丙噁唑草(oxadiargyl)、噁草灵(oxadiazon)、噁杀草敏(oxapyrazon)、噁杀草敏-二甲氨基乙醇(oxapyrazon-dimolamine)、噁杀草敏-钠、环丙氧磺隆(oxasulfuron)、氯噁嗪草(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、对伏隆(parafluron)、百草枯(paraquat)、百草枯二氯化物(paraquatdichloride)、二甲硫酸百草枯(paraquatdimetilsulfate)、克草猛(pebulate)、壬酸(pelargonicacid)、胺硝草(pendimethalin)、五氟磺草胺(penoxsulam)、五氯酚(pentachlorophenol)、甲氯酰草胺(pentanochlor)、戊噁唑草(pentoxazone)、氟草磺胺(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙基、稀草隆(phenobenzuron)、乙酸苯汞、氨氯吡啶酸(picloram)、氨氯吡啶酸-2-乙基己基、氨氯吡啶酸-异辛基、氨氯吡啶酸-甲基、氨氯吡啶酸-乙醇胺、氨氯吡啶酸-钾、氨氯吡啶酸-三乙基铵、氨氯吡啶酸-三(2-羟基丙基)铵、氟吡草胺(picolinafen)、pinoxaden、哌草磷(piperophos)、亚砷酸钾(potassiumarsenite)、叠氮化钾(potassiumazide)、氰酸钾(potassiumazide)、冰草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆-甲基、环氰津(procyazine)、氨氟乐灵(prodiamine)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、丙草止津(proglinazine)、丙草止津-乙基、扑灭通(prometon)、扑草净(prometryn)、毒草安(propachlor)、敌稗(propanil)、喔草酯(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟丙磺隆(prosulfuron)、扑灭生(proxan)、扑灭生-钠、广草胺(prynachlor)、比达农(pydanon)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate)、吡嘧磺隆(pyrazosulfuron)、乙基吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、嘧苯草肟(pyribenzoxim)、稗草丹(pyributicarb)、氯草定(pyriclor)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、甲基肟啶草(pyriminobac-methyl)、pyrimisulfan、嘧硫草醚(pyrithiobac)、嘧硫草醚钠、pyroxasulfone、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、喹禾灵(quizalofop)、乙基喹禾灵(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精乙基喹禾灵(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、硫氰苯乙胺(rhodethanil)、玉嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、另丁津(sebuthylazine)、密草通(secbumeton)、稀禾定(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西玛通(simeton)、西草净(simetryn)、氯乙酸(SMA)、S-异丙甲草胺(S-metolachlor)、亚砷酸钠(sodiumarsenite)、叠氮化钠(sodiumazide)、氯酸钠(sodiumchlorate)、磺草酮(sulcotrione)、草克死(sulfallate)、磺胺草唑(sulfentrazone)、嘧磺隆(sulfometuron)、甲基嘧磺隆(sulfometuron-methyl)、乙磺磺隆(sulfosulfuron)、硫酸(sulfuricacid)、吖庚磺酯(sulglycapin)、灭草灵(swep)、三氯醋酸(TCA)、三氯醋酸铵、三氯醋酸钙、乙二基三氯醋酸(TCA-ethadyl)、三氯醋酸镁、三氯醋酸钠、牧草胺(tebutam)、丁唑隆(tebuthiuron)、tefuryltrione、tembotrione、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、猛杀草(terbuchlor)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、氟氧隆(tetrafluron)、噻醚草胺(thenylchlor)、赛唑隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑胺(thidiazimin)、赛二唑素(thidiazuron)、噻酮磺隆(thiencarbazone)、噻酮磺隆-甲基(thiencarbazone-methyl)、噻磺隆(thifensulfuron)、甲基噻磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、丁草威(tiocarbazil)、嘧草胺(tioclorim)、topramezone、苯草酮(tralkoxydim)、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、甲基苯磺隆(tribenuron-methyl)、杀草畏(tricamba)、三氯吡氧乙酸(triclopyr)、丁氧基乙基三氯吡氧乙酸(triclopyr-butotyl)、乙基三氯吡氧乙酸(triclopyr-ethyl)、三氯吡氧乙酸-三乙基铵(triclopyr-triethylammonium)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆-甲基(triflusulfuron-methyl)、三氟苯氧丙酸(trifop)、三氟苯氧丙酸-甲基(trifop-methyl)、三氟禾草肟(trifopsime)、三羟基三嗪(trihydroxytriazine)、三甲隆(trimeturon)、茚草酮(tripropindan)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、灭草猛(vernolate)或二甲苯草胺(xylachlor)。
杀生物剂
式I化合物也可与一种或多种生物杀虫剂联用(诸如在组合混合物中或同时或先后施用)。术语“生物杀虫剂”用于以与化学杀虫剂类似的方式施用的微生物虫害生物防治药物(MICROBIALBIOLOGICALPESTCONTROLAGENT)。通常这些为细菌防治药物,但是也有真菌防治药物的实例,包括木霉菌(Trichodermaspp.)和白粉寄生孢(Ampelomycesquisqualis)(用于葡萄霜霉病(grapepowderymildew)的防治药物)。枯草杆菌(Bacillussubtilis)用于防治植物病原体。杂草和啮齿动物也已用微生物药物防治。一种熟知的杀虫剂实例为苏芸金杆菌(Bacillusthuringiensis),为鳞翅目、鞘翅目和双翅目的细菌性疾病。由于其对其它生物几乎不具有作用,所以认为其相比于合成杀虫剂更为环境友善的。生物杀虫剂包括根据下述的产物:
1.昆虫病原真菌(例如绿僵菌(Metarhiziumanisopliae));
2.昆虫病原线虫(例如芜菁夜蛾斯氏线虫(Steinernemafeltiae));及
3.昆虫病原病毒(例如苹果蠢蛾颗粒体病毒(Cydiapomonellagranulovirus))。
昆虫病原生物的其它实例包括但不限于杆状病毒、细菌和其它原核生物、真菌、原生动物和Microsproridia。生物学衍生的杀虫剂包括但不限于鱼藤酮、藜芦定及微生物毒素;昆虫耐受或抵抗的植物种类;及经重组体DNA技术修饰的生物,由此产生杀虫剂或向经遗传修饰的生物体传达昆虫耐受性质。在一种实施方式中,式I的分子可与一种或多种生物杀虫剂在种子处理和土壤改良的区域内使用。TheManualofBiocontrolAgents给出了对可用生物杀虫剂(及其它基于生物学的防治)产物的综述。CoppingL.G.(ed.)(2004).TheManualofBiocontrolAgents(formerlytheBiopesticideManual)3rdEdition.BritishCropProductionCouncil(BCPC),Farnham,SurreyUK。
其它活性化合物
式I化合物也可与一种或多种以下化合物联用(诸如在组合混合物中或同时或先后施用):
1.3-(4-氯-2,6-二甲基苯基)-4-羟基-8-氧杂-1-氮杂螺[4,5]癸-3-烯-2-酮;
2.3-(4’-氯-2,4-二甲基[1,1’-联苯]-3-基)-4-羟基-8-氧杂-1-氮杂螺[4,5]癸-3-烯-2-酮;
3.4-[[(6-氯吡啶-3-基)甲基]甲基氨基]-呋喃-2(5H)-酮;
4.4-[[(6-氯吡啶-3-基)甲基]环丙基氨基]-呋喃-2(5H)-酮;
5.3-氯-N2-[(1S)-1-甲基-2-(甲基磺酰基)乙基]-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二甲酰胺;
6.2-氰基-N-乙基-4-氟-3-甲氧基-苯磺酰胺;
7.2-氰基-N-乙基-3-甲氧基-苯磺酰胺;
8.2-氰基-3-二氟甲氧基-N-乙基-4-氟-苯磺酰胺;
9.2-氰基-3-氟甲氧基-N-乙基-苯磺酰胺;
10.2-氰基-6-氟-3-甲氧基-N,N-二甲基-苯磺酰胺;
11.2-氰基-N-乙基-6-氟-3-甲氧基-N-甲基-苯磺酰胺;
12.2-氰基-3-二氟甲氧基-N,N-二甲基苯磺酰胺;
13.3-(二氟甲基)-N-[2-(3,3-二甲基丁基)苯基]-1-甲基-1H-吡唑-4-甲酰胺;
14.N-乙基-2,2-二甲基丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙;
15.N-乙基-2,2-二氯-1-甲基环丙烷-甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙烟碱(N-乙基-2,2-DICHLORO-1-METHYLCYCLOPROPANE-CARBOXAMIDE-2-(2,6-DICHLORO-Α,Α,Α-TRIFLUORO-P-TOLYL)HYDRAZONENICOTINE);
16.硫代碳酸O-{(E-)-[2-(4-氯-苯基)-2-氰基-1-(2-三氟甲基苯基)-乙烯基]}·S-甲基酯;
17.(E)-N1-[(2-氯-1,3-噻唑-5-基甲基)]-N2-氰基-N1-甲基乙脒;
18.1-(6-氯吡啶-3-基甲基)-7-甲基-8-硝基-1,2,3,5,6,7-六氢-咪唑并[1,2-A]吡啶-5-醇;
19.甲磺酸4-[4-氯苯基-(2-亚丁基-亚肼基)甲基)]苯基酯(4-[4-CHLOROPHENYL-(2-BUTYLIDINE-HYDRAZONO)METHYL)]PHENYLMESYLATE);及
20.N-乙基-2,2-二氯-1-甲基环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙。
式I化合物也可与一种或多种以下化合物联用(诸如在组合混合物中或同时或先后施用):杀藻剂、抗饲育剂、杀鸟剂、杀菌剂、驱鸟剂、化学绝育剂、除草剂安全剂、昆虫引诱剂、昆虫驱避剂、哺乳动物驱避剂、交配扰乱剂、杀软体动物剂、植物活化剂、植物生长调节剂、杀啮齿动物剂、或杀病毒剂。
协同混合物和协同剂
式I化合物可与至少一种其它杀虫剂组合使用以形成协同性混合物,其中所述化合物的作用模式相比于式I化合物的作用模式是相同、相似或不同的。作用模式的实例包括但不限于:乙酰胆碱酯酶抑制剂;钠通道调节剂;壳多糖生物合成抑制剂(chitinbiosynthesisinhibitor);GABA和谷氨酸门控氯离子通道拮抗剂(GABAandglutamate-gatedchloridechannelantagonist);GABA和谷氨酸门控氯离子通道激动剂(GABAandglutamate-gatedchloridechannelagonist);乙酰胆碱受体激动剂;乙酰胆碱受体拮抗剂;METI抑制剂;Mg刺激ATP酶抑制剂(Mg-stimulatedATPaseinhibitor);烟碱性乙酰胆碱受体;中肠膜破裂剂(midgutmembranedisrupter);氧化磷酸化中断剂(oxidativephosphorylationdisrupter)和莱恩素受体(ryanodinereceptor(RyRs))。
此外,式I化合物可与杀真菌剂、杀螨剂、除草剂或杀线虫剂中的至少一种组合使用以形成协同混合物。
此外,式I化合物可与其它活性化合物组合使用以形成协同混合物,例如标题“其它活性化合物”下的化合物杀藻剂、杀鸟剂、杀菌剂、杀软体动物剂、杀啮齿动物剂、杀病毒剂、除草剂安全剂、辅料、和/或表面活性剂。而且,以下化合物称为协同剂并且可以与式I化合物组合使用:胡椒基丁醚(piperonylbutoxide)、增效醛(piprotal)、增效酯(propylisome)、增效菊(sesamex)、芝麻啉(sesamolin)、亚砜、和脱叶磷(tribufos)。
制剂
杀虫剂几乎不适于以其纯形式来施用。通常需要加入其它物质,从而使杀虫剂可按所需要的浓度和合适的形式来使用,由此易于施用、处理、运输、贮存和使杀虫剂活性最大化。因此,将杀虫剂配制成例如诱饵(bait)、浓缩乳液、粉剂(dust)、乳油(emulsifiableconcentrate)、熏蒸剂(fumigant)、凝胶、颗粒、微囊形式(microencapsulation)、种子处理形式(seedtreatment)、混悬浓缩物、混悬乳液(suspoemulsion)、片剂、水溶性液体、水可分散颗粒或干燥可流动物(dryflowable)、可润湿粉末(wettablepowder)和超低体积溶液(ultraLowvolumesolution)。有关制剂类型的进一步信息请参阅“CatalogueofPesticideFormulationTypesandInternationalCodingSystem”TechnicalMonographn°2,5thEditionbyCropLifeInternational(2002)。
杀虫剂最通常以由所述杀虫剂的浓缩制剂制备的含水混悬液或乳液的形式来施用。这样的水溶性制剂、水可混悬制剂或可乳化制剂为固体(通常已知为可润湿粉末或水可分散颗粒)或液体(通常已知为乳油或含水混悬液)。可润湿粉末(其可以被压制以形成水可分散颗粒)包含杀虫剂、载体和表面活性剂的充分混合物(intimatemixture)。杀虫剂的浓度通常为约10wt%(重量百分比)至约90wt%。所述载体通常选自硅镁土(attapulgiteclay)、蒙脱土(montmorilloniteclay)、硅藻土(diatomaceousearth)或精制硅酸盐(purifiedsilicate)。有效的表面活性剂(占可润湿粉末的约0.5%至约10%)选自磺酸化的木质素、浓缩的萘磺酸盐、萘磺酸盐、烷基苯磺酸盐、烷基硫酸盐和非离子表面活性剂(例如烷基酚的环氧乙烷加成物)。
杀虫剂的乳油包含溶于载体(所述载体为水可混合溶剂或水不可混合有机溶剂和乳化剂的混合物)中的合适浓度的杀虫剂(例如每升液体约50至约500克)。有用的有机溶剂包括芳族溶剂(特别是二甲苯)和石油馏分(特别是石油的高沸点萘部分和烯烃部分例如重芳族石脑油)。也可使用其它有机溶剂,例如萜类溶剂(包括松香衍生物)、脂肪族酮(例如环己酮)和复杂的醇(例如2-乙氧基乙醇)。用于乳油的合适乳化剂选自常见的阴离子表面活性剂和非离子表面活性剂。
含水混悬液包括水不溶性杀虫剂分散在含水载体中的混悬液,其浓度为约5wt%至约50wt%。混悬液如下制备:精细研磨所述杀虫剂且将其剧烈混合到载体中,所述载体包含水和表面活性剂。也可加入像无机盐和合成胶或天然胶那样的成分,以增加含水载体的密度和粘度。通常最有效的是通过在设备例如砂磨机(sandmill)、球磨机(ballmill)或活塞式匀化器(piston-typehomogenizer)中制备含水混合物并对其进行匀化来同时研磨和混合杀虫剂。
杀虫剂也可按颗粒组合物的形式来施用,所述颗粒组合物特别可用于施用到土壤中。颗粒组合物通常含有分散在载体中的约0.5wt%至约10wt%的所述杀虫剂,所述载体包含粘土(clay)或相似的物质。上述组合物通常如下制备:将所述杀虫剂溶于合适的溶剂中且将其施用到颗粒载体上,所述颗粒载体已被预先制成合适的粒度(范围为约0.5至3mm)。上述组合物也可如下制备:将所述载体和化合物制成面团状或糊状,然后压碎并干燥,从而得到所需颗粒粒度。
含有杀虫剂的粉剂如下制备:对粉末状的杀虫剂与合适的粉尘状农用载体(例如高岭粘土、研碎的火山石等)进行充分混合。粉剂可合适地含有约1%至约10%杀虫剂。它们可用于拌种(seeddressing)或与粉尘鼓风机一起用于叶面施用(foliageapplication)。
同样可行的是施用溶液形式的杀虫剂(在广泛用于农业化学的合适有机溶剂(通常为石油(petroleumoil)例如喷雾油)中)。
杀虫剂也可按气溶胶组合物的形式来施用。在这样的组合物中,将杀虫剂溶解或分散在载体中,所述载体为可产生压力的推进剂混合物。将所述气溶胶组合物包装在容器中,通过雾化阀使所述混合物从所述容器中分散出来。
当将杀虫剂与食物或引诱剂混合或与食物和引诱剂混合时,形成了杀虫剂诱饵。当害虫吃掉诱饵时,它们也消耗了杀虫剂。诱饵可呈颗粒、凝胶、可流动粉末、液体或固体的形式。它们用在害虫藏身处。
熏蒸剂是具有相对高蒸汽压的杀虫剂,因此可按气体形式存在,其以足够的浓度杀死土壤或密封空间中的害虫。熏蒸剂的毒性与其浓度和暴露时间成比例。它们的特征在于具有良好的扩散能力并通过渗透到害虫的呼吸系统中或通过害虫的表皮被吸收来发挥作用。施用熏蒸剂以便在气密房间或气密建筑物中或在专门腔室中对防气片(gasproofsheet)下的储藏产品害虫(storedproductpest)进行防治。
可通过将杀虫剂粒子或小滴混悬在各种类型的塑性聚合物(plasticpolymer)中来对杀虫剂进行微囊化。通过改变聚合物的化学性质或通过改变处理中的因素,可形成各种大小、各种溶解度、各种壁厚度和各种渗透度的微囊。这些因素控制其中活性成分的释放速度,而释放速度又影响产品的残留性能、作用速度和气味。
通过将杀虫剂溶于使杀虫剂保持为溶液形式的溶剂中来制备油溶液浓缩物。杀虫剂的油溶液由于溶剂本身具有杀虫作用和体被(integument)蜡质覆盖物(waxycovering)的溶解增加了杀虫剂的摄取速度而通常提供比其它制剂更快的击倒及杀死害虫作用。油溶液的其它优点包括更好的贮藏稳定性、更好的裂缝渗透性和更好的油腻表面粘附性。
另一种实施方式是水包油型乳剂,其中所述乳剂包含油性小球(oilyglobule),所述油性小球各自提供有层状液晶包衣(lamellarliquidcrystalcoating)并分散在水相中,其中每个油性小球包含至少一种具有农业活性的化合物并各自包衣有单层的层或几层的层,所述层包含(1)至少一种非离子性亲脂性表面活性剂、(2)至少一种非离子性亲水性表面活性剂和(3)至少一种离子性表面活性剂,其中所述小球具有小于800纳米的平均粒径。有关该实施方案的进一步信息公开在美国专利公开文本20070027034(公开日期为2007年2月1日且专利申请号为11/495,228)中。为了易于使用,将该实施方式称作“OIWE”。
进一步信息请参阅“InsectPestManagement”2ndEditionbyD.Dent,copyrightCABInternational(2000)。另外,更多详细信息请参阅“HandbookofPestControl-TheBehavior,LifeHistory,andControlofHouseholdPests”byArnoldMallis,9thEdition,copyright2004byGIEMediaInc。
其它制剂组分
一般地,当式I化合物或其任何农业上可接受的盐在制剂中使用时,所述制剂也可含有其它组分。这些组分包括但不限于(这是非穷举性且非相互排斥性的列举)润湿剂、展布剂(spreader)、粘着剂、渗透剂、缓冲剂、隔离剂(sequesteringagent)、防飘移剂(driftreductionagent)、相容剂(compatibilityagent)、消泡剂、清洁剂和乳化剂。接下来描述了几种组分。
润湿剂是这样的物质,当将其加到液体中时,所述物质通过降低液体和液体在其上展布的表面之间的界面张力来增加液体的展布或渗透能力。润湿剂在农用化学制剂中发挥两种主要功能:在处理和制造期间增加粉末在水中的润湿速率从而制备在可溶性液体中的浓缩物或混悬浓缩物;和在将产品与水在喷雾罐中混合期间降低可润湿粉末的润湿时间并改善水向水可分散颗粒中的渗透。用于可润湿粉末、混悬浓缩物和水可分散颗粒制剂中的润湿剂的实例有月桂基硫酸钠、二辛基磺基琥珀酸钠(sodiumdioctylsulphosuccinate)、烷基酚乙氧基化物和脂肪醇乙氧基化物。
分散剂是这样的物质,其吸附到粒子的表面上并有助于保持粒子的分散状态及防止粒子重新聚集。将分散剂加到农用化学制剂中以有助于制造期间的分散和混悬且有助于确保粒子在喷雾罐中重新分散到水中。它们广泛用于可润湿粉末、混悬浓缩物和水可分散颗粒中。用作分散剂的表面活性剂具有牢固吸附到粒子表面上的能力并提供对抗粒子重新聚集的荷电屏障或立体屏障。最常用的表面活性剂是阴离子型表面活性剂、非离子型表面活性剂或这两种类型的混合物。对于可润湿粉末制剂而言,最常见的分散剂为木质素磺酸钠(sodiumlignosulphonate)。对于混悬浓缩物而言,使用聚电解质(polyelectrolyte)如萘磺酸钠甲醛缩合物(sodiumnaphthalenesulphonateformaldehydecondensate)来得到非常好的吸附和稳定作用。也使用三苯乙烯基苯酚乙氧基化物磷酸酯(tristyrylphenolethoxylatephosphateester)。非离子型表面活性剂(如烷基芳基环氧乙烷缩合物(alkylarylethyleneoxidecondensate)和EO-PO嵌段共聚物)有时与阴离子型表面活性剂组合起来作为用于混悬浓缩物的分散剂。近年来,已开发了分子量非常高的聚合物表面活性剂的新类型作为分散剂。这些分散剂具有非常长的疏水性“骨架”和形成“梳”状表面活性剂的“齿”的很多个环氧乙烷链。这些高分子量聚合物可为混悬浓缩物提供非常好的长期稳定性,这是因为疏水性骨架具有固定到粒子表面上的多个锚点。用于农用化学制剂中的分散剂的实例有木质素磺酸钠、萘磺酸钠甲醛缩合物、三苯乙烯基苯酚乙氧基化物磷酸酯、脂肪醇乙氧基化物、烷基乙氧基化物、EO-PO嵌段共聚物和接枝共聚物。
乳化剂是使一种液相的小滴于另一种液相中的混悬液稳定的物质。在没有乳化剂的情况下,两种液体会分离成两个不可混合的液相。最常用的乳化剂共混物含有具有12个或更多个环氧乙烷单元的烷基酚或脂肪醇及十二烷基苯磺酸的油溶性钙盐。范围为8至18的亲水亲油平衡(“HLB”)值通常将提供良好的稳定乳剂。乳剂稳定性有时可通过加入少量EO-PO嵌段共聚物表面活性剂来改善。
增溶剂是在浓度超过临界胶束浓度时在水中形成胶束的表面活性剂。然后,胶束能够在胶束的疏水部分内溶解或增溶水不溶性物质。通常用于增溶的表面活性剂类型是非离子型表面活性剂:脱水山梨糖醇单油酸酯(sorbitanmonooleate)、脱水山梨糖醇单油酸酯乙氧基化物(sorbitanmonooleateethoxylate)和油酸甲酯(methyloleateester)。
表面活性剂有时单独使用,或有时与其它添加剂(如作为喷雾罐混合物辅料的矿物油或植物油)一起使用以改善杀虫剂对靶标的生物性能。用于生物增强(bioenhancement)的表面活性剂类型通常取决于杀虫剂的性质和作用模式。然而,它们通常是非离子型的,如烷基乙氧基化物、线性脂肪醇乙氧基化物、脂肪族胺乙氧基化物。
农业制剂中的载体或稀释剂是加到杀虫剂中以得到所需强度产品的物质。载体通常是具有高吸收能力(absorptivecapacity)的物质,而稀释剂通常是具有低吸收能力的物质。载体和稀释剂用在粉剂制剂、可润湿粉末制剂、颗粒制剂和水可分散颗粒制剂中。
有机溶剂主要用在乳油制剂、水包油乳剂、混悬乳剂和超低容量制剂中及以较小的程度用在颗粒制剂中。有时使用溶剂的混合物。第一主要组的溶剂有脂肪族石蜡基油(paraffinicoil),如煤油或精炼石蜡。第二主要组及最常见的溶剂包括芳族溶剂,如二甲苯和分子量较高的馏分即C9和C10芳族溶剂。氯代烃可用作共溶剂以当将制剂乳化到水中时防止杀虫剂的结晶。有时醇类用作共溶剂以增加溶剂能力(solventpower)。其它溶剂可包括植物油、种子油及植物油和种子油的酯。
增稠剂或胶凝剂主要用在混悬浓缩物制剂、乳剂制剂和混悬乳剂制剂中以改变液体的流变学或流动性并防止经分散的颗粒或小滴发生分离或沉降。增稠剂、胶凝剂和抗沉降剂通常分为两类即水不溶性粒子和水溶性聚合物。使用粘土和硅石来产生混悬浓缩物制剂是可能的。这些类型的物质的实例包括但不限于蒙脱石,如膨润土;硅酸镁铝;和活性白土(attapulgite)。水溶性多糖已用作增稠-胶凝剂多年。最常用的多糖的类型为种子或海藻的天然提取物或为纤维素的合成衍生物。这些类型的物质的实例包括但不限于瓜尔胶、豆角胶(locustbeangum)、角叉菜胶(carrageenam)、藻酸盐、甲基纤维素、羧甲基纤维素钠(SCMC)、羟乙基纤维素(HEC)。其它类型的抗沉降剂基于变性淀粉、聚丙烯酸酯、聚乙烯醇和聚环氧乙烷。另一种良好的抗沉降剂为黄原胶。
微生物引起所配制产品的酸败(spoilage)。因此防腐剂用于消除或减小微生物的作用。这些试剂的实例包括但不限于丙酸及其钠盐、山梨酸及其钠盐或钾盐、苯甲酸及其钠盐、对羟基苯甲酸钠盐、对羟基苯甲酸甲酯和1,2-苯并异噻唑啉-3-酮(BIT)。
表面活性剂的存在通常导致水基制剂当生产和通过喷雾罐施用时在混合操作期间起泡。为了减小起泡倾向,通常在生产阶段或在装入瓶中前加入消泡剂。一般而言,有两种类型的消泡剂即硅氧烷和非硅氧烷。硅氧烷通常为聚二甲基硅氧烷的水性乳剂,而非硅氧烷消泡剂为水不溶性油如辛醇和壬醇,或者二氧化硅。在这两种情况下,消泡剂的功能都是从空气-水界面中置换表面活性剂。
“绿色”试剂(例如辅料、表面活性剂、溶剂)可降低作物保护制剂的整体环境覆盖面积。绿色试剂为生物可降解的且通常由天然和/或可持续性来源例如植物和动物来源获得。特殊实例为:植物油、种子油及植物油和种子油的酯,及烷氧基化烷基多聚葡萄糖苷。
进一步信息请参阅“ChemistryandTechnologyofAgrochemicalFormulations”editedbyD.A.Knowles,copyright1998byKluwerAcademicPublishers。还请参阅“InsecticidesinAgricultureandEnvironment-RetrospectsandProspects”byA.S.Perry,I.Yamamoto,I.Ishaaya,andR.Perry,copyright1998bySpringer-Verlag。
杀虫活性
公开的杀虫组合物可以用作,例如,杀线虫剂、杀螨剂、杀虫剂、杀昆虫剂、杀螨剂、和/或杀软体动物剂。
在一种特定的实施方式中,防治害虫的方法包括将包含式I化合物或其任何农业上可接受的盐的杀虫组合物施用于害虫群体附近。
式I化合物通常以每公顷约0.01克的量至每公顷约5000克的量使用以进行防治。优选为每公顷约0.1克的量至每公顷约500克的量且通常更优选的是每公顷约1克的量至每公顷约50的量。
式I化合物施用的区域可为害虫占据(或可为寄居或经过)的任何区域,例如:作物、树木、果实、谷类、饲料、藤本植物、草丛和观赏植物生长的区域;家养动物居住的区域;建筑物的内或外表面(诸如谷物储存的位置)、建筑物中使用的建筑材料(诸如浸渍木材)及建筑物周围的土壤。使用式I的分子的特定作物区域包括苹果、玉米、向日葵、棉花、大豆、芸苔、小麦、大米、高粱、大麦、燕麦、土豆、橙子、苜蓿、莴苣、草莓、番茄、胡椒、十字花科植物、梨、烟草、杏仁、甜菜、豆类和其它有价值的作物生长或其种子即将播种的区域。同样有利的是在各种植物生长时与式I化合物一起使用硫酸铵。
防治害虫通常表示害虫群体、害虫活动性或两者在区域内降低。这可在如下情况时发生:害虫群体由区域驱除;害虫在区域内或在区域周围无能力;或害虫整体或部分在区域内或在区域周围灭绝。当然,可出现这些结果的组合。一般来说,害虫群体、活动性或两者预期地降低了多于50%,更优选的多于90%。一般来说,区域不在人类中或表面;因此,位置通常为非人类区域。
式I化合物可以混合物的形式使用,同时或先后施用、单独或与其它增强植物活力(例如长出更好的根系、更好地经受应激生长条件)的化合物一起施用。所述其它化合物为例如调节植物乙烯受体(最新的是1-甲基环丙烯(也称为1-MCP))的化合物。而且,这种分子可在害虫活性低时使用,例如在正在生长的植物开始产生有价值的农产品之前。这种时期包括害虫压力通常很低的早期播种季节。
式I化合物可施用至植物的叶子和果实部分以防治害虫。所述分子将直接与害虫接触,或害虫在侵蚀含有杀虫剂的叶子、果实或浸出的树液时消耗所述杀虫剂。式I化合物也可施用至土壤且当以该种方式施用时,可防治进食根和茎的害虫。所述根可吸收分子,将其吸取至植物的叶子部分以防治在地上的咀嚼口器害虫和进食树液的害虫。
一般而言,就诱饵而言,将诱饵置于例如白蚁可与诱饵发生接触和/或依附的场所。也可将诱饵施用到例如蚂蚁、白蚁、蟑螂和苍蝇可与诱饵发生接触和/或依附的建筑物表面(水平表面、垂直表面或倾斜表面)。诱饵可包含式I化合物。
式I化合物可包囊在胶囊的内部或置于胶囊的表面。胶囊的大小可在纳米尺寸(直径约100-900纳米)至微米尺寸(直径约10-900微米)的范围内。
由于一些害虫的卵具有抗杀虫剂作用的独特能力,因此可能需要重复施用式I化合物以防治新出现的幼虫。
杀虫剂在植物中的系统移动可用于通过将式I化合物施用(例如在区域内喷雾)到所述植物的不同部位而对所述植物的另一个部位进行害虫防治。例如,防治食叶昆虫可以通过滴注灌溉施用或沟槽施用、通过将土壤用例如种植之前或之后土壤浇灌(drench),或通过种植前处理种子来实现。
种子处理可以施用于所有类型的种子,包括可生长成基因修饰为表达特定属性的植物的那些种子。代表性的实例包括表达对无脊椎害虫(例如苏芸金杆菌(Bacillusthuringiensis))有毒的蛋白质或其它杀虫毒素,表达除草剂抵抗性的那些种子(例如“RoundupReady”种子)或具有“叠加”外源基因的那些种子(所述“叠加”外源基因表达杀虫毒素、除草剂抵抗性、营养提高特性或任何其它有益特性)。另外,用式I化合物进行的所述种子处理可进一步增强植物更好经受应激生长条件的能力。这导致更健康更旺盛的植物,由此可在收获时得到更高的产量。一般来说,每100,000个种子施用约1克至约500克的式I或II的3-(噻唑-2-基)吡啶1-氧化物化合物和/或化合物C3或其任何农业上可接受的盐可预期地得到好的益处,每100,000个种子约10克至约100克的量可预期地得到更好的益处且每100,000个种子约25克至约75克的量可预期地得到甚至更好的益处。
容易理解的是,式I化合物可用于被基因修饰以表达特定属性,例如苏芸金杆菌或其它杀虫毒素,或表达除草剂抵抗性的那些植物,或具有“叠加”外源基因的植物,所述“叠加”外源基因表达杀虫毒素、除草剂抵抗性、营养提高特性或任何其它有益特性。
式I化合物可用于在兽医学方面或在非人动物饲养领域防治内寄生物(endoparasite)和外寄生物(ectoparasite)。式I化合物在以如下方式来施用:以例如片剂、胶囊剂、饮用剂、颗粒剂的形式来口服给药,以例如浸蘸、喷雾、倾倒、点样和撒粉的形式来进行皮肤施用,及以例如注射剂的形式来进行肠胃外给药。
式I化合物也可有利地用于家畜饲养(例如牛、羊、猪、鸡和鹅)。它们也可在宠物诸如马、狗和猫中有利地采用。待防治的特定害虫可为对所述动物造成麻烦的蚤和蜱。将合适的制剂与饮用水或饲料一起口服给予动物。合适的剂量和制剂取决于物种。
式I化合物也可用于防治上面列举的动物中的寄生虫,尤其是肠的寄生虫。
式I化合物也可在用于人类保健的治疗方法中采用。所述方法包括但不限于以例如片剂、胶囊剂、饮用剂、颗粒剂的形式来口服给药及通过皮肤施用。
全世界的害虫正在迁移至新环境(对于这种害虫),然后在这种新环境中变成新的侵害物种。式I化合物也可在这种新的侵害物种上使用以在这种新环境中防治它们。
式I化合物也可在这样的区域中使用,其中植物如农作物正在生长(例如,种植前、种植期间、收获前)以及其中存在低水平的(甚至没有实际存在)可在商业上损害这种植物的害虫。这种分子在这种区域中的用途是使在该区域中生长的植物受益。这种益处可包括但不限于改善植物的健康,改善植物的收率(例如,提高的生物量和/或提高的有价值成分含量),改善植物活力(例如,改善的植物生长和/或更绿的叶子),改善的植物质量(例如,改善的某些成分的含量或组成)和改善植物对非生物和/或生物应激的耐受性。
在杀虫剂可被使用或商业销售前,所述杀虫剂经历各种政府当局(当地、地区、州、国家、国际)的漫长评价过程。大量数据要求(voluminousdatarequirement)由管理当局来规定且必须通过数据生成(datageneration)来给出(address),及由产品登记人或由代表产品登记人的其他人来提交,其中通常使用与互联网连接的电脑。这些政府当局然后评价所述数据且若作出安全性的决定,则将产品登记许可(productregistrationapproval)提供给潜在的使用者或销售者。之后,在产品登记被授权和支持的地方,所述使用者或销售者可使用或销售这些杀虫剂。
可测试式I化合物以测定它对于害虫的效力。而且,可进行作用模式研究以测定是否所述分子具有与其它杀虫剂不同的作用模式。然后,可将这些采集到的数据例如通过因特网传播至第三方。
公开的包含式I化合物的杀虫组合物可以用于防治多种害虫。
作为非限制性实例,在一种或多种实施方式中,本申请的方法可以用于防治一种或多种下述成员:Lyriomizasativae,Caliothripsphaseoli,Paratriozacockerel,甜菜夜蛾(Spodopteraexigua),桃蚜(Myzuspersicae),褐飞虱(Nilaparvatalugens)和烟粉虱(Bemisiatabaci)。
在另外的实施方式中,本申请的方法可以用于防治选自以下至少一种的一个或多个成员:节肢动物门(PhylumArthropoda),线虫门(PhylumNematoda),螯肢亚门(SubphylumChelicerata),多足亚门(SubphylumMyriapoda),六足亚门(SubphylumHexapoda),昆虫纲(ClassInsecta),蛛形纲(ClassArachnida),和综合纲(ClassSymphyla)。在至少一些实施方式中,本申请的方法可以用于防治选自以下至少一种的一个或多个成员:昆虫纲和蛛形纲。
在进一步的实施方式中,本申请的方法可以用于防治鞘翅目(Coleoptera)害虫(甲虫),包括但不限于,豆象属种(Acanthoscelidesspp.)(象虫(weevils))、菜豆象(Acanthoscelidesobtectus)(普通豌豆象)、白蜡窄吉丁(Agrilusplanipennis)(花曲柳窄吉丁)、金针虫属种(AgriotesSpp.)(金针虫(Wireworm))、光肩星天牛(Anoplophoraglabripennis)(亚洲长角天牛)、棉铃象属种(AnthonomusSpp.)(象甲科)、墨西哥棉铃象(AnthonomusGrandis)(棉铃虫)、茧蜂属种(AphidiusSpp.)、象甲属种(ApionSpp.)(象虫)、甘蔗金龟属种(ApogoniaSpp.)(蛴螬)、黑绒金龟(Ataeniusspretulus)(黑绒金龟子)、甜菜隐食甲(AtomariaLinearis)(小舌甘菜甲虫(pygmymangoldbeetle))、守瓜属禾中(AulacophoreSpp.)、甜菜象(Bothynoderespunctiventris)(甜菜根象虫(beetrootweevil)),豆象属种(Bruchusspp.)(象虫),豌豆象(BruchusPisorum)(豌豆象虫(peaweevil))、Cacoesia属种(Cacoesiaspp.)、四纹豆象(Callosobruchusmaculatus)(南方豇豆象虫(southerncowpeaweevil))、黄斑露尾甲(Carpophilushemipteras)(干果甲虫(driedfruitbeetle))、甜菜龟甲(Cassidavittata)、天牛属种(Cerosternaspp.)、Cerotoma属种(Cerotomaspp.)(金滴虫(chrysomelids))、菜豆萤叶甲(Cerotomatrifurcate)(豆叶甲(beanleafbeetle))、象鼻虫属(Ceutorhynchusspp.)(象虫)、白菜籽龟象(Ceutorhynchusassimilis)(白菜象鼻虫(cabbageseedpodweevil))、芫菁龟象(Ceutorhynchusnapi)(卷心菜象鼻虫(cabbagecurculio))、跳甲属(Chaetocnemaspp.)(叶甲(chrysomelids))、肖叶甲属(Colaspisspp.)(土甲虫(soilbeetles))、Conoderusscalaris、Conoderusstigmosus、李象(Conotrachelusnenuphar)(梅锥象甲(plumcurculio))、Cotinusnitidis(绿金龟(GreenJunebeetle))、石刁柏负泥虫(CriocerisAsparagi)(石刁柏甲虫)、锈赤扁谷盗(CryptolestesFerrugineus)(锈谷甲虫(rustygrainbeetle))、长角扁谷盗(CryptolestesPusillus)(扁谷盗)、土耳其扁谷盗(CryptolestesTurcicus)(土耳其谷甲虫(turkishgrainbeetle))、Ctenicera属种(Cteniceraspp.)(线虫)、象虫属种(Curculiospp.)(象虫)、圆头犀金龟属(Cyclocephalaspp.)(蛴螬)、密点细枝象(Cylindrocpturusadspersus)(太阳花莲象虫(sunflowerstemweevil))、芒果剪叶象(Deporausmarginatus)(芒果剪叶象虫(mangoleaf-cuttingweevil))、火腿皮蠹(Dermesteslardarius)(火腿皮蠹)、白腹皮蠹(Dermestesmaculates)(白腹皮蠹)、叶甲属(Diabroticaspp.)(chrysomelids)、墨西哥豆瓢虫(Epilachnavarivestis)(墨西哥豆甲虫)、蛀茎象甲(Faustinuscubae)、苍白根颈象(Hylobiuspales)(好斗象甲(palesweevil))、叶象属种(Hyperaspp.)(象虫)、紫苜蓿叶象(Hyperapostica)(苜蓿叶象虫(alfalfaweevil))、Hyperdoes属种(Hyperdoesspp.)(Hyperodesweevil)、咖啡果小蠹(Hypothenemushampei)(咖啡果甲虫)、齿小蠹属种(Ipsspp.)(棘胫小蠹(engravers))、烟草甲(Lasiodermaserricorne)(烟草甲虫(cigarettebeetle))、马铃薯甲虫(Leptinotarsadecemlineata)(马铃薯甲虫)、Liogenysfuscus、Liogenyssuturalis、稻水象甲(Lissorhoptrusoryzophilus)(稻水象虫(ricewaterweevil))、粉蠹属种(Lyctusspp.)(木蠹蛾(woodbeetles)/粉蠹甲虫(powderpostbeetles))、Maecolaspisjoliveti、Megascelis属种(Megascelisspp.)、玉米叩甲(Melanotuscommunis)、Meligethes属种(Meligethesspp.)、油菜花露尾甲(Meligethesaeneus)(花甲虫(blossombeetle))、五月金龟子(Melolonthamelolontha)(普通欧洲金龟子(commonEuropeancockchafer))、Obereabrevis、线形筒天牛(Oberealinearis)、椰蛀犀金龟(Oryctesrhinoceros)(datepalmbeetle)、贸易锯谷盗(Oryzaephilusmercator)(大眼锯谷盗(merchantgrainbeetle))、锯谷盗(Oryzaephilussurinamensis)(锯齿谷甲虫(sawtoothedgrainbeetle))、象甲属种(Otiorhynchusspp.)(象虫)、黑角负泥虫(Oulemamelanopus)(橙足负泥虫(cerealleafbeetle))、水稻负泥虫(Oulemaoryzae)、玫瑰短喙象属种(Pantomorusspp.)(象虫)、食叶鳃金龟属种(Phyllophagaspp.)(五月/六月金龟子)、Phyllophagacuyabana(叶甲科昆虫)、苹虎象属种(Phynchitesspp.)、日本弧丽金龟(Popilliajaponica)(日本金龟子)、大谷蠹(Prostephanustruncates)(大谷长蠹(largergrainborer))、谷蠹(Rhizoperthadominica)(谷蠹(lessergrainborer))、根鳃金龟属种(Rhizotrogusspp.)(欧洲金龟子(Europeanchafer))、隐颏象属种(Rhynchophorusspp.)(象虫)、小蠹属种(Scolytusspp.)(木蠹蛾)、Shenophorus属种(Shenophorusspp.)(谷象)、豌豆叶象(Sitonalineatus)(豌豆叶象甲(pealeafweevil))、米象属种(Sitophilusspp.)(谷象甲)、谷象(Sitophilusgranaries)(谷象)、米象(Sitophilusoryzae)(米象)、药材甲(Stegobiumpaniceum)(药材甲(drugstorebeetle))、拟谷盗属种(Triboliumspp.)(面象虫)、赤拟谷盗(Triboliumcastaneum)(赤拟谷盗(redflourbeetle))、杂拟谷盗(Triboliumconfusum)(扁拟谷盗(confusedflourbeetle))、花斑皮蠹(Trogodermavariabile)(仓库皮蠹(warehousebeetle))、和Zabrustenebioides。
在其它实施方式中,本申请的方法可以用于防治革翅目(Dermaptera)害虫(蠼螋(earwigs))。
在另外的实施方式中,本申请的方法可以用于防治脉翅目(Dictyoptera)害虫(蟑螂(cockroaches)),包括但不限于,德国小蠊(Blattellagermanica)(德国蟑螂(Germancockroach))、东方蜚蠊(Blattaorientalis)(东方蜚蠊(orientalcockroach))、宾夕法尼亚木蠊(Parcoblattapennylvanica)、美洲大蠊(Periplanetaamericana)(美洲蟑螂(Americancockroach))、澳洲大蠊(Periplanetaaustraloasiae)(澳洲蟑螂(Australiancockroach))、褐色大蠊(Periplanetabrunnea)(褐色蟑螂(browncockroach))、烟色大蠊(Periplanetafuliginosa)(黑胸大蠊(smokybrowncockroach))、蔗绿蜚蠊(Pyncoselussuninamensis)(Surinamcockroach)、和长须蜚蠊(Supellalongipalpa)(褐带蜚蠊(brownbandedcockroach))。
在进一步的实施方式中,本申请的方法可以用于防治双翅目(Diptera)害虫(苍蝇(trueflies)),包括但不限于,伊蚊属种(Aedesspp.)(蚊)、紫苜蓿潜蝇(Agromyzafrontella)(苜蓿潜叶蝇(alfalfablotchleafminer))、潜蝇属种(Agromyzaspp.)(潜叶蝇)、按实蝇属种(Anastrephaspp.)(果蝇)、加勒比按实蝇(Anastrephasuspense)(加勒比果蝇)、疟蚊属种(Anophelesspp.)(蚊)、果实蝇属种(Bactroceraspp.)(果蝇)、瓜实蝇(Bactroceracucurbitae)(瓜蝇(melonfly))、桔小实蝇(Bactroceradorsalis)(东方果蝇(orientalfruitfly))、小条实蝇属种(Ceratitisspp.)(果蝇)、地中海小条实蝇(Ceratitiscapitata)(地中海果蝇)、斑虻属种(Chrysopsspp.)(斑虻(deerflies))、锥蝇属种(Cochliomyiaspp.)(螺旋蛆(screwworms))、瘿蚊属种(Contariniaspp.)(瘿蚊(Gallmidges))、库蚊属种(Culexspp.)(蚊)、叶瘿蚊属(Dasineuraspp.)(瘿蚊(gallmidges))、油菜叶瘿蚊(Dasineurabrassicae)(甘蓝瘿蚊(cabbagegallmidge))、地种蝇属种(Deliaspp.)、灰地种蝇(Deliaplatura)(种蝇(seedcornmaggot))、果蝇属种(Drosophilaspp.)(醋蝇(vinegarflies))、厕蝇属种(Fanniaspp.)(家蝇(filthflies))、黄腹厕蝇(Fanniacanicularis)(夏厕蝇(littlehousefly))、灰腹厕蝇(Fanniascalaris)(灰腹厕蝇(latrinefly))、肠胃蝇(Gasterophilusintestinalis)(马胃蝇(horsebotfly))、Gracilliaperseae、扰血蝇(Haematobiairritans)(角蝇(hornfly))、黑蝇属种(Hylemyiaspp.)(根蛆(rootmaggots))、纹皮蝇(Hypodermalineatum)(纹皮蝇(commoncattlegrub))、斑潜蝇属种(Liriomyzaspp.)(潜叶蝇)、甘蓝斑潜蝇(Liriomyzabrassica)(蛇行潜叶蝇(serpentineleafminer))、绵羊虱蝇(Melophagusovinus)(绵羊虱(sheepked))、蝇属种(Muscaspp.)(家蝇(muscidflies))、秋家蝇(Muscaautumnalis)(面蝇(facefly))、家蝇(Muscadomestica)(家蝇)、羊狂蝇(Oestrusovis)(羊鼻蝇(sheepbotfly))、欧洲麦秆蝇(Oscinellafrit)(瑞典麦秆蝇(fritfly))、甜菜泉蝇(Pegomyiabetae)(甜菜潜叶花蝇(beetleafminer))、种蝇属种(Phorbiaspp.)、胡萝卜茎蝇(Psilarosae)(胡萝卜锈蝇(carrotrustfly))、樱桃果蝇(Rhagoletiscerasi)(樱桃果蝇)、苹果实蝇(Rhagoletispomonella)(苹果蛆(applemaggot))、麦红吸浆虫(Sitodiplosismosellana)(麦红吸浆虫(orangewheatblossommidge))、厩螫蝇(Stomoxyscalcitrans)(厩螫蝇)、牛虻属种(Tabanusspp.)(马蝇)、和大蚊属(Tipulaspp.)(大蚊(craneflies))。
在其它实施方式中,本申请的方法可以用于防治半翅目(Hemiptera)害虫(蝽(truebugs)),包括但不限于,拟绿蝽(Acrosternumhilare)(绿蝽(greenstinkbug))、美洲谷长蝽(Blissusleucopterus)(长蝽(chinchbug))、马铃薯俊盲蝽(Calocorisnorvegicus)(马铃薯盲蝽(potatomirid))、热带臭虫(Cimexhemipterus)(热带臭虫)、臭虫(Cimexlectularius)(臭虫)、Dagbertusfasciatus、Dichelopsfurcatus、美棉红蝽(Dysdercussuturellus)(污棉虫)、Edessameditabunda、欧扁盾蝽(Eurygastermaura)(谷物虫(cerealbug))、Euschistusheros、褐美洲蝽(Euschistusservus)(褐臭蝽(brownstinkbug))、安氏角盲蝽(Helopeltisantonii)、茶角盲蝽(Helopeltistheivora)(teablightplantbug)、蝽属种(Lagynotomusspp.)(蝽(stinkbugs))、Leptocorisaoratorius、Leptocorisavaricornis、草盲蝽属种(Lygusspp.)(plantbugs)、豆荚草盲蝽(Lygushesperus)(westerntarnishedplantbug)、木槿曼粉蚧(Maconellicoccushirsutus)、Neurocolpuslongirostris、稻绿蝽(Nezaraviridula)(南方绿蝽象(southerngreenstinkbug))、植盲蝽属种(Phytocorisspp.)(盲蝽象(plantbugs))、Phytocoriscalifornicus、Phytocorisrelativus、Piezodorusguildinii、四蚊盲蝽(Poecilocapsuslineatus)(fourlinedplantbug)、Psallusvaccinicola、Pseudacystaperseae、Scaptocoriscastanea、和锥蝽属种(Triatomaspp.)(bloodsuckingconenosebugs/kissingbugs)。
在另外的实施方式中,本申请的方法可以用于防治同翅目(Homoptera)害虫(蚜虫(aphids)、蚧(scales)、粉虱(whiteflies)、叶蝉(leaflhoppers)),包括但不限于,豌豆蚜(Acrythosiphonpisum)(豌豆蚜)、球蚜属种(Adelgesspp.)(球蚜)、甘蓝粉虱(Aleurodesproletella)(卷心菜粉虱)、螺旋粉虱(Aleurodicusdisperses)、丝绒粉虱(Aleurothrixusfloccosus)(棉粉虱(woollywhitefly))、轮盾蚧属种(Aluacaspisspp.)、Amrascabigutellabigutella、Aphrophora属种(Aphrophoraspp.)(leafhoppers)、红圆蚧(Aonidiellaaurantii)(加利福尼亚红蚧(Californiaredscale))、蚜虫属种(Aphisspp.)(蚜虫)、棉蚜(Aphisgossypii)(棉蚜)、苹果蚜(Aphispomi)(苹果蚜(appleaphid))、马铃薯长须蚜(Aulacorthumsolani)(foxgloveaphid)、粉虱属种(Bemisiaspp.)(粉虱)、银叶粉虱(Bemisiaargentifolii)、甘薯粉虱(Bemisiatabaci)(甘薯粉虱)、麦双尾蚜(Brachycolusnoxius)(俄罗斯蚜(Russianaphid))、天门冬小管蚜(Brachycorynellaasparagi)(芦笋蚜虫(asparagusaphid))、Brevenniarehi、甘蓝蚜(Brevicorynebrassicae)(甘蓝蚜)、蜡蚧属种(Ceroplastesspp.)(蚧)、红蜡蚧(Ceroplastesrubens)(红蜡蚧)、雪盾蚧属种(Chionaspisspp.)(蚧)、圆盾蚧属种(Chrysomphalusspp.)(蚧)、软蜡蚧属种(Coccusspp.)(蚧)、车前圆尾蚜(Dysaphisplantaginea)(红苹果棉蚜(rosyappleaphid))、绿小叶蝉属种(Empoascaspp.)(leafhoppers)、苹果棉蚜(Eriosomalanigerum)(苹果棉蚜(woollyappleaphid))、吹棉蚧(Iceryapurchasi)(吹棉蚧(cottonycushionscale))、芒果黄线叶蝉(Idioscopusnitidulus)(芒果叶蝉(mangoleafhopper))、灰飞虱(Laodelphaxstriatellus)(小褐飞虱(smallerbrownplanthopper))、蛎盾蚧属种(Lepidosaphesspp.)、长管蚜属种(Macrosiphumspp.)、大戟长管蚜(Macrosiphumeuphorbiae)(马铃薯蚜(potatoaphid))、麦长管蚜(Macrosiphumgranarium)(麦长管蚜(Englishgrainaphid))、蔷薇长管蚜(Macrosiphumrosae)(玫瑰蚜)、Macrostelesquadrilineatus(asterleafhopper)、Mahanarvafrimbiolata、麦无网蚜(Metopolophiumdirhodum)(玫瑰麦长管蚜(rosegrainaphid))、Mictislongicornis、瘤额蚜属种(Myzusspp.)、桃蚜(Myzuspersicae)(绿桃蚜(greenpeachaphid))、黑尾叶蝉属种(Nephotettixspp.)(叶蝉)、黑尾叶蝉(Nephotettixcinctipes)(绿叶蝉)、褐飞虱(Nilaparvatalugens)(褐飞虱(brownplanthopper))、糠片盾蚧(Parlatoriapergandii)(chaffscale)、黑片盾蚧(Parlatoriaziziphi)(乌木蚧(ebonyscale))、玉米花翅飞虱(Peregrinusmaidis)(corndelphacid)、沫蝉属种(Philaenusspp.)(沫蝉)、葡萄根瘤蚜(Phylloxeravitifoliae)(葡萄根瘤蚜(grapephylloxera))、去杉球蚧(Physokermespiceae)(云杉圆盾蚧(sprucebudscale))、臀纹粉蚧属种(Planococcusspp.)(粉蚧)、粉蚧属种(Pseudococcusspp.)(粉蚧)、菠萝洁粉蚧(Pseudococcusbrevipes)(菠萝粉蚧(pineapplemealybug))、梨园盾蚧(Quadraspidiotusperniciosus)(梨园盾蚧(SanJosescale))、溢管蚜属种(Rhopalosiphumspp.)(蚜虫)、玉米蚜(Rhopalosiphummaida)(玉米叶蚜(cornleafaphid))、禾谷溢管蚜(Rhapalosiphumpadi)(oatbird-cherryaphid)、珠蜡蚧属种(Saissetiaspp.)(蚧)、榄珠蜡蚧(Saissetiaoleae)(黑蚧(blackscale))、麦二叉蚜(Schizaphisgraminum)(绿蚜(greenbug))、麦长管蚜(Sitobionavenae)(英国麦蚜(Englishgrainaphid))、白背飞虱(Sogatellafurcifera)(白背飞虱(white-backedplanthopper))、珠蜡蚧属种(Therioaphisspp.)(蚜虫)、龟蚧属种(Toumeyellaspp.)(蚧)、声蚜属种(Toxopteraspp.)(蚜虫)、结翅粉虱属种(Trialeurodesspp.)(粉虱)、温室粉虱(Trialeurodesvaporariorum)(温室粉虱(greenhousewhitefly))、结翅粉虱(Trialeurodesabutiloneus)(bandedwingwhitefly)、尖盾蚧属种(Unaspisspp.)(蚧)、矢尖蚧(Unaspisyanonensis)(箭头蚧(arrowheadscale))、和Zuliaentreriana。在至少一些实施方式中,本申请的方法可以用于防治桃蚜(Myzuspersicae)。
在其它实施方式中,本申请的方法可以用于防治膜翅目(Hymenoptera)害虫(蚂蚁、黄蜂和蜜蜂),包括但不限于,切叶蚁属种(Acromyrrmexspp.)、新疆菜叶蜂(Athaliarosae)、叶蚁属种(Attaspp.)(切叶蚁(leafcuttingants))、黑蚁属种(Camponotusspp.)(木蚁(carpenterants))、松叶蜂属种(Diprionspp.)(钜蝇)、蚁属种(Formicaspp.)(蚂蚁)、阿根廷蚁(Iridomyrmexhumilis)(阿根廷蚁(Argentineant))、厨蚁属种(Monomoriumspp.)、小家蚁(Monomoriumminimum)(小黑蚁(littleblackant))、厨蚁(Monomoriumpharaonis)(法老蚁(Pharaohant))、厨蚁属种(Neodiprionspp.)(钜蝇)、收获蚁属种(Pogonomyrmexspp.)(收获蚁)、马蜂属种(Polistesspp.)(胡蜂(paperwasps))、火蚁属种(Solenopsisspp.)(火蚁)、酸臭蚁(Tapoinomasessile)(臭家蚁(odoroushouseant))、铺道蚁属种(Tetranomoriumspp.)(铺道蚁(pavementants))、黄胡蜂属种(Vespulaspp.)(小黄蜂(yellowjackets))、和木蜂属种(Xylocopaspp.)(木蜂(carpenterbees))。
在某些实施方式中,本申请的方法可以用于防治等翅目(Isoptera)害虫(白蚁(termites)),包括但不限于,乳白蚁属种(Coptotermesspp.)、曲颚白蚁(Coptotermescurvignathus)、新西兰乳白蚁(Coptotermesfrenchii)、台湾乳白蚁(Coptotermesformosanus)(Formosansubterraneantermite)、角白蚁属种(Cornitermesspp.)(长鼻白蚁(nasutetermites))、砂白蚁属种(Cryptotermesspp.)(干木白蚁)、异白蚁属种(Heterotermesspp.)(沙漠土栖白蚁(desertsubterraneantermites))、金黄异白蚁(Heterotermesaureus)、木白蚁属种(Kalotermesspp.)(干木白蚁)、楹白蚁属种(Incistitermesspp.)(干木白蚁)、大白蚁属种(Macrotermesspp.)(真菌生长白蚁(fungusgrowingtermites))、缘木白蚁属种(Marginitermesspp.)(干木白蚁)、锯白蚁属种(Microcerotermesspp.)(草白蚁(harvestertermites))、稻麦小白蚁(Microtermesobesi)、原角白蚁属种(Procornitermesspp.)、散白蚁属种(Reticulitermesspp.)(土栖白蚁)、Reticulitermesbanyulensis、Reticulitermesgrassei、黄肢散白蚁(Reticulitermesflavipes)(东方土栖白蚁)、美小黄散白蚁(Reticulitermeshageni)、西方散白蚁(Reticulitermeshesperus)(西方土栖白蚁)、桑特散白蚁(Reticulitermessantonensis)、栖北散白蚁(Reticulitermessperatus)、美黑胫散白蚁(Reticulitermestibialis)、美小黑散白蚁(Reticulitermesvirginicus)、长鼻白蚁属种(Schedorhinotermesspp.)、和古白蚁属种(Zootermopsisspp.)(腐木白蚁(rotten-woodtermites))。
在另外的实施方式中,本申请的方法可以用于防治鳞翅目(Lepidoptera)害虫(蛾和蝶),包括但不限于,飞扬阿夜蛾(Achoeajanata)、褐带卷蛾属种(Adoxophyesspp.)、棉褐带卷蛾(Adoxophyesorana)、地虎属种(Agrotisspp.)(切根虫)、小地蚕(Agrotisipsilon)(黑切根虫(blackcutworm))、棉叶波纹夜蛾(Alabamaargillacea)(棉叶虫(cottonleafworm))、Amorbiacuneana、Amyelosistransitella(脐橙螟(navelorangeworm))、Anacamptodesdefectaria、桃条麦蛾(Anarsialineatella)(桃枝麦蛾(peachtwigborer))、黄麻桥夜蛾(Anomissabulifera)(jutelooper)、黎豆夜蛾(Anticarsiagemmatalis)(velvetbeancaterpillar)、果树卷叶蛾(Archipsargyrospila)(fruittreeleafroller)、玫瑰卷叶蛾(Archipsrosana)(roseleafroller)、卷蛾属种(Argyrotaeniaspp.)(tortricidmoths)、桔带卷蛾(Argyrotaeniacitrana)(桔卷叶蛾(orangetortrix))、Autographagamma、Bonagotacranaodes、籼弄蝶(Borbocinnara)(稻纵卷叶螟(riceleaffolder))、Bucculatrixthurberiella(cottonleafperforator)、细蛾属种(Caloptiliaspp.)(潜叶虫(leafminers))、Capuareticulana、桃蛀果蛾(Carposinaniponensis)(peachfruitmoth)、禾草螟属种(Chilospp.)、芒果横线尾夜蛾(Chlumetiatransversa)(mangoshootborer)、玫瑰色卷蛾(Choristoneurarosaceana)(蔷薇斜条卷叶蛾(obliquebandedleafroller))、夜蛾属种(Chrysodeixisspp.)、稻纵卷叶野螟(Cnaphalocerusmedinalis)(grassleafroller)、豆粉蝶属种(Coliasspp.)、荔枝爻纹细蛾(Conpomorphacramerella)、芳香木蠹蛾(Cossuscossus)(木蠹蛾(carpentermoth))、草螟属种(Crambusspp.)(草地螟(Sodwebworms))、李小食心虫(Cydiafunebrana)(梅果蛾(plumfruitmoth))、梨小食心虫(Cydiamolesta)(东方果蛾(orientalfruitmoth))、Cydianignicana(豌豆蛾(peamoth))、苹果小卷蛾(Cydiapomonella)(苹果蠹蛾(codlingmoth))、Darnadiducta、绢野螟属种(Diaphaniaspp.)(螟虫(stemborers))、螟属种(Diatraeaspp.)(stalkborers)、小蔗螟(Diatraeasaccharalis)(甘蔗螟(sugarcaneborer))、西南玉米杆草螟(Diatraeagraniosella)(西南玉米螟(southwestercornborer))、金刚钻属种(Eariasspp.)(棉铃虫)、埃及金刚钻(Eariasinsulata)(埃及棉铃虫)、翠纹金刚钻(Eariasvitella)(roughnorthernbollworm)、Ecdytopophaaurantianum、南美玉米苗斑螟(Elasmopalpuslignosellus)(小玉米茎蛀虫(lessercornstalkborer))、Epiphysiaspostruttana(苹果浅褐卷叶蛾(lightbrownapplemoth))、粉斑螟属种(Ephestiaspp.)(flourmoths)、粉斑螟(Ephestiacautella)(almondmoth)、烟草粉斑螟(Ephestiaelutella)(烟草蛾(tobbacomoth))、地中海粉螟(Ephestiakuehniella)(地中海粉蛾(Mediterraneanflourmoth))、Epimeces属种(Epimecesspp.)、夜小卷蛾(Epinotiaaporema)、香蕉弄蝶(Erionotathrax)(bananaskipper)、女贞细卷蛾(Eupoeciliaambiguella)(葡萄卷叶蛾(grapeberrymoth))、Euxoaauxiliaris(原切根虫(armycutworm))、Feltia属种(Feltiaspp.)(切根虫)、角剑夜蛾属种(Gortynaspp.)(螟蛾(stemborers))、东方蛀果蛾(Grapholitamolesta)(东方果蛾(orientalfruitmoth))、三纹螟蛾(Hedyleptaindicate)(豆卷叶螟(beanleafwebber))、青虫属种(Helicoverpaspp.)(夜蛾)、棉铃虫(Helicoverpaarmigera)(cottonbollworm)、谷实夜蛾(Helicoverpazea)(螟蛉/玉米铃虫)、实夜蛾属种(Heliothisspp.)(夜蛾)、烟芽夜蛾(Heliothisvirescens)(烟草芽虫(tobaccobudworm))、菜心野螟(Hellulaundalis)(cabbagewebworm)、Indarbela属种(Indarbelaspp.)(根茎天牛(rootborers))、番茄蠹蛾(Keiferialycopersicella)(番茄蛲虫(tomatopinworm))、茄白翅野螟(Leucinodesorbonalis)(eggplantfruitborer)、旋纹潜蛾(Leucopteramalifoliella)、细蛾属种(Lithocollectisspp.)、葡萄小卷叶蛾(Lobesiabotrana)(葡萄果实蛾(grapefruitmoth))、Loxagrotis属种(Loxagrotisspp.)(夜蛾)、Loxagrotisalbicosta(西部豆类切根虫(westernbeancutworm))、舞毒蛾(Lymantriadispar)(吉普赛蛾(gypsymoth))、桃潜蛾(Lyonetiaclerkella)(金纹细蛾(appleleafminer))、Mahasenacorbetti(油棕榈袋蛾(oilpalmbagworm))、天幕毛虫属种(Malacosomaspp.)(tentcaterpillars)、甘蓝夜蛾(Mamestrabrassicae)(cabbagearmyworm)、豆荚野螟(Marucatestulalis)(豆野螟(beanpodborer))、袋蛾(Metisaplana)(袋蛾)、Mythimnaunipuncta(truearmyworm)、Neoleucinodeselegantalis(小番茄螟(smalltomatoborer))、三点水螟(Nymphuladepunctalis)(稻纵卷叶螟(ricecaseworm))、冬尺蠖(Operophtherabrumata)(冬蛾(wintermoth))、玉米螟(Ostrinianubilalis)(欧洲玉米螟(Europeancornborer))、Oxydiavesulia、Pandemiscerasana(普通葡萄卷叶蛾(commoncurranttortrix))、苹褐卷蛾(Pandemisheparana)(brownappletortrix)、非洲达摩凤蝶(Papiliodemodocus)、红铃麦蛾(Pectinophoragossypiella)(红铃虫(pinkbollworm))、Peridroma属种(Peridromaspp.)(切根虫)、杂色地老虎(Peridromasaucia)(杂色切根虫(variegatedcutworm))、咖啡潜叶蛾(Perileucopteracoffeella)(白咖啡潜叶蛾(whitecoffeeleafminer))、马铃薯块茎蛾(Phthorimaeaoperculella)(potatotubermoth)、柑桔叶潜蛾(Phyllocnisitiscitrella)、细蛾属种(Phyllonorycterspp.)(潜叶蛾)、菜粉蝶(Pierisrapae)(进口菜青虫(importedcabbageworm))、苜蓿绿夜蛾(Plathypenascabra)、印度谷斑蛾(Plodiainterpunctella)(印度谷螟(Indianmealmoth))、菜蛾(Plutellaxylostella)(小菜蛾(diamondbackmoth))、Polychrosisviteana(葡萄卷叶蛾(grapeberrymoth))、桔果巢蛾(Praysendocarpa)、油橄榄巢蛾(Praysoleae)(油橄榄蛾(olivemoth))、Pseudaletia属种(Pseudaletiaspp.)(夜蛾)、Pseudaletiaunipunctata(夜盗蛾(armyworm))、大豆夜蛾(Pseudoplusiaincludes)(大豆尺蠖(soybeanlooper))、尺蠖(Rachiplusianu)、三化螟(Scirpophagaincertulas)、蛀茎夜蛾属种(Sesamiaspp.)(螟蛾(stemborers))、稻蛀茎夜蛾(Sesamiainferens)(pinkricestemborer)、粉茎螟(Sesamianonagrioides)、铜斑褐刺蛾(Setoranitens)、麦蛾(Sitotrogacerealella)(Angoumoisgrainmoth)、葡萄长须卷蛾(Sparganothispilleriana)、灰翅夜蛾属种(Spodopteraspp.)(夜盗蛾)、甜菜夜蛾(Spodopteraexigua)(甜菜夜盗蛾(beetarmyworm))、草地贪夜蛾(Spodopterafugiperda)(秋夜盗蛾(fallarmyworm))、南部灰翅夜蛾(Spodopteraoridania)(南方夜盗蛾(southernarmyworm))、兴透翅蛾属种(Synanthedonspp.)(rootborers)、Theclabasilides、Thermisiagemmatalis、衣蛾(Tineolabisselliella)(负袋夜蛾(webbingclothesmoth))、粉斑夜蛾(Trichoplusiani)(菜青虫)、番茄斑潜蝇(Tutaabsoluta)、巢蛾属种(Yponomeutaspp.)、咖啡豹蠹蛾(Zeuzeracoffeae)(红枝虫(redbranchborer))、和梨豹蠹蛾(Zeuzerapyrina)(豹蠹蛾(leopardmoth))。在至少一些实施方式中,本申请的方法可以用于防治甜菜夜蛾。
本申请的方法也可以用于防治食毛目(Mallophaga)害虫(羽虱(chewinglice)),包括但不限于,绵羊虱(Bovicolaovis)(sheepbitinglouse)、火鸡短角鸟虱(Menacanthusstramineus)(鸡体虱(chickenbodylouse))、和鸡羽虱(Menopongallinea)(普通鸡虱(commonhenlouse))。
在另外的实施方式中,本申请的方法可以用于防治直翅目(Orthoptera)害虫(蚱蜢、蝗虫和蟋蟀),包括但不限于,黑斑阿纳螽(Anabrussimplex)(摩门蟋蟀(Mormoncricket))、蝼蛄(Gryllotalpidae)(蝼蛄)、东亚飞蝗(Locustamigratoria)、蚱蜢属种(Melanoplusspp.)(蚱蜢)、纲翅细刺螽(Microcentrumretinerve)(角翅蝈蝈(angularwingedkatydid))、Pterophylla种(Pterophyllaspp.)(蝈蝈(kaydids))、沙漠蝗(chistocercagregaria)、叉尾斯奎螽(Scudderiafurcata)(forktailedbushkatydid)、和黑角隆脊蝗(Valanganigricorni)。
在其它实施方式中,本申请的方法可以用于防治虱目(Phthiraptera)害虫(吸吮虱(suckinglice)),包括但不限于,吸血虱属种(Haematopinusspp.)(牛虱和猪虱)、绵羊颚虱(Linognathusovillus)(羊虱)、头虱(Pediculushumanuscapitis)(人体虱(humanbodylouse))、体虱(Pediculushumanushumanus)(人体虱(humanbodylice))、和阴虱(Pthiruspubis)(蟹虱(crablouse))。
在特定的实施方式中,本申请的方法可以用于防治蚤目(Siphonaptera)(跳蚤),包括但不限于,犬栉头蚤(Ctenocephalidescanis)(狗跳蚤(dogflea))、猫栉头蚤(Ctenocephalidesfelis)(猫跳蚤(catflea))、和人蚤(Pulexirritans)(humanflea)。
在另外的实施方式中,本申请的方法可以用于防治缨翅目(Thysanoptera)害虫(蓟马),包括但不限于,烟褐蓟马(Frankliniellafusca)(烟草蓟马(tobaccothrips))、苜蓿花蓟马(Frankliniellaoccidentalis)(西方花蓟马(westernflowerthrips))、Frankliniellashultzei、Frankliniellawilliamsi(谷物蓟马(cornthrips))、温室蓟马(Heliothripshaemorrhaidalis)(温室蓟马(greenhousethrips))、腹钩针蓟马(Riphiphorothripscruentatus)、硬蓟马属种(Scirtothripsspp.)、桔硬蓟马(Scirtothripscitri)(柑橘蓟马(citrusthrips))、茶黄蓟马(Scirtothripsdorsalis)(茶黄蓟马(yellowteathrips))、Taeniothripsrhopalantennalis、和蓟马属种(Thripsspp.)。
本申请的方法可以用于防治缨尾目(Thysanura)(蠹虫(bristletails)),包括但不限于,衣鱼属种(Lepismaspp.)(蠹虫(silverfish))和小灶衣鱼属种(Thermobiaspp.)(小灶衣鱼(firebrats))。
在进一步的实施方式中,本申请的方法可以用于防治螨目(Acari)(螨(mite)和蜱(tick)),包括但不限于,伍氏蜂盾螨(Acarapsiswoodi)(trachealmiteofhoneybees)、粉螨属种(Acarusspp.)(食物螨)、粗脚粉螨(Acarussiro)(谷物螨(grainmite))、芒果芽螨(Aceriamangiferae)(mangobudmite)、刺皮瘿螨属种(Aculopsspp.)、番茄刺皮瘿螨(Aculopslycopersici)(tomatorussetmite)、Aculopspelekasi、桔刺皮瘿螨(Aculuspelekassi)、斯氏刺瘿螨(Aculusschlechtendali)(苹果锈螨(applerustmite))、Amblyommaamericanum(孤星蜱(lonestartick))、牛蜱属种(Boophilusspp.)(蜱)、卵形短须螨(Brevipalpusobovatus)(privetmite)、紫红短须螨(Brevipalpusphoenicis)(红黑扁螨(redandblackflatmite))、脂螨属种(Demodexspp.)(疥癣螨(mangemites))、革蜱属种(Dermacentorspp.)(硬蜱)、美洲狗蜱(Dermacentorvariabilis)(americandogtick)、屋尘螨(Dermatophagoidespteronyssinus)(housedustmite)、Eotetranycus属种(Eotetranycusspp.)、鹅耳枥始叶螨(Eotetranychuscarpini)(黄蜘蛛螨(yellowspidermite))、上瘿螨属种(Epitimerusspp.)、瘿螨属种(Eriophyesspp.)、硬蜱属种(Ixodesspp.)(蜱)、Metatetranycus属种(Metatetranycusspp.)、猫耳螨(Notoedrescati)、小爪螨属种(Oligonychusspp.)、咖啡小爪螨(Oligonychuscoffee)、冬青小爪螨(Oligonychusilicus)(南方红螨(southernredmite))、全爪螨属种(Panonychusspp.)、柑桔全爪螨(Panonychuscitri)(柑橘红螨(citrusredmite))、苹果全爪螨(Panonychusulmi)(欧洲红螨(Europeanredmite))、桔皱叶刺瘿螨(Phyllocoptrutaoleivora)(柑橘锈螨(citrusrustmite))、食跗线螨属(Polyphagotarsonemunlatus)(广明螨(broadmite))、血红扇头蜱(Rhipicephalussanguineus)(褐色犬蜱(browndogtick))、根螨属种(Rhizoglyphusspp.)(bulbmites)、疥螨(Sarcoptesscabiei)(itchmite)、鳄梨顶冠瘿螨(Tegolophusperseaflorae)、叶螨属种(Tetranychusspp.)、二点叶螨(Tetranychusurticae)(twospottedspidermite)、和狄氏瓦螨(Varroadestructor)(honeybeemite)。
在另外的实施方式中,本申请的方法可以用于防治线虫目(Nematoda)害虫(线虫),包括但不限于,滑刃线虫属种(Aphelenchoidesspp.)(叶线虫)、刺线虫属种(Belonolaimusspp.)(刺线虫(stingnematodes))、小环线虫属种(Criconemellaspp.)(环线虫(ringnematodes))、犬恶丝虫(Dirofilariaimmitis)(dogheartworm)、茎线虫属种(Ditylenchusspp.)(stemandbulbnematodes)、棘皮线虫属种(Heteroderaspp.)(胞囊线虫(cystnematodes))、玉米胞囊线虫(Heteroderazeae)(corncystnematode)、潜根线虫属种(Hirschmanniellaspp.)(根线虫(rootnematodes))、纽带线虫属种(Hoplolaimusspp.)(矛线虫(lancenematodes))、根结线虫属种(Meloidogynespp.)(根结线虫(rootknotnematodes))、南方根结线虫(Meloidogyneincognita)(根结线虫)、旋盘尾丝虫(Onchocercavolvulus)(hook-tailworm)、短体线虫属种(Pratylenchusspp.)(lesionnematodes)、穿孔线虫属种(Radopholusspp.)(穴居线虫(burrowingnematodes))、和香蕉肾状线虫(Rotylenchusreniformis)(肾状线虫(kidney-shapednematode))。
在至少一些实施方式中,本申请的方法可以用于防治以下一种或多种纲的至少一种害虫和蜱螨目(Acari)中至少一种小虫:鳞翅目(Lepidoptera)、鞘蛾目(Coleoptera)、同翅目(Homoptera)、半翅目(Hemiptera)、缨翅目(Thysanoptera)、等翅目(Isoptera)、直翅目(Orthoptera)、双翅目(Diptera)、膜翅目(Hymenoptera)、和蚤目(Siphonaptera)。
杀虫测试
实施例A:桃蚜(GreenPeachAphid)(Myzuspersicae)(GPA)(桃蚜(MYZUPE))的生物测定。
桃蚜(Myzuspersicae)是桃树的最重要的蚜虫害虫,导致减少的生长、叶子的干皱和各种组织的死亡。它也是危险的,因为它充当植物病毒运输的传病媒介,例如马铃薯Y病毒和马铃薯卷叶病毒(对于龙葵/马铃薯家族茄科的成员),和各种花叶病病毒(对于许多其它粮食作物)。GPA攻击诸如以下的植物:绿花椰菜、牛蒡、白菜、胡萝卜、花椰菜、萝卜(daikon)、茄子、菜豆、莴苣、澳大利亚坚果、番木瓜、胡椒、蕃薯、番茄、水田芥菜和西葫芦等。GPA也攻击许多观赏作物如康乃馨、菊花、开花白菜(floweringwhitecabbage)、猩猩木和玫瑰。GPA已经形成了对许多杀虫剂的耐药性。
将在7.6cm罐(pot)中生长的卷心菜幼苗(具有2-3片小的(3-5cm)真叶(trueleaf))用作试验底物。用20-50个桃蚜(无翅成虫和若虫阶段)对所述幼苗进行侵害1天,然后进行化学施用。每种处理使用具有各株幼苗的四个罐。将试验化合物(2mg)溶于2mL丙酮/甲醇(1:1)溶剂中,形成浓度为1000ppm试验化合物的储备溶液。储备溶液用0.025%吐温20在水中的溶液稀释5倍以得到浓度为200ppm的测试化合物溶液。使用手持抽吸器型喷雾器将溶液喷雾到卷心菜叶子的两面直到形成径流(runoff)。对照植物(溶剂检测)用仅含20体积%丙酮/甲醇(1:1)溶剂的稀释剂喷雾。将经处理的植物在保育室中在约25℃和环境相对湿度(RH)的条件下保持三天,然后评级。评价通过在显微镜下计数每株植物上的活蚜虫数目来进行。百分比防治通过使用Abbott校正公式(W.S.Abbott,“AMethodofComputingtheEffectivenessofanInsecticide”J.Econ.Entomol.18(1925),pp.265-267)如下测量。
经校正的百分比防治=100*(X-Y)/X
其中
X=溶剂检测植物上的活蚜虫数目,以及
Y=经处理的植物上的活蚜虫数目
结果显示在题目为“表2.桃蚜(GPA)(MYZUPE)和甘薯粉虱(SweetpotatoWhitefly-crawler(WF))(BEMITA)的生物学数据”的表(参见表部分)中。
实施例B:在叶片喷雾试验中对甘薯粉虱(SweetpotatoWhitefly-crawler)(烟粉虱(Bemisiatabaci))(WF)(甘薯粉虱(BEMITA))进行的杀虫测试。
已经报告甘薯粉虱(烟粉虱(Bemisiatabaci))是全球种植作物的严重害虫。其具有极广的宿主范围,可攻击来自63个植物家族的多于500种植物。杂草通常用作作物害虫的替补宿主。直接的伺食伤害是通过刺穿植物叶片并从植物叶片吸吮树液来引起的。这种伺食导致植物衰弱和早期萎蔫并降低植物生长速率和产量。间接伤害是通过由粉虱产生的甘汁积累导致的。甘汁用作叶子和果实上黑色烟霉(blacksootymold)生长底物,减少其光合作用,并降低植物的市场价值或产量。当甘薯粉虱携带植物病毒时,也会导致伤害。认为甘薯粉虱是世界上植物病毒最普遍和重要的粉虱载体。
将在7.6cm罐中生长的棉花植物(陆地棉)(具有1片小的(4-5cm)真叶)用作试验底物。用200-400个粉虱卵侵害植物4-5天,然后进行化学施用。对于每一处理,使用四株棉花植物。将试验化合物(2mg)溶于1mL丙酮溶剂中,形成浓度为2000ppm试验化合物的储备溶液。储备溶液用0.025%吐温20在水中的溶液(稀释剂)稀释10倍以得到浓度为200ppm的测试化合物溶液。使用手持抽吸器型喷雾器将溶液喷雾到棉花叶子的两面直到形成径流。对照植物(溶剂检测)用仅含10体积%丙酮溶剂的稀释剂喷雾。将经处理的植物在保育室中在约25℃和环境相对湿度(RH)的条件下保持9天,然后评级。评价通过在显微镜下计数每株植物上的活的3-4若虫期害虫数目来进行。百分比防治通过使用Abbott校正公式(W.S.Abbott,“AMethodofComputingtheEffectivenessofanInsecticide”J.Econ.Entomol.18(1925),pp.265-267)如下测量。
经校正的百分比防治=100*(X-Y)/X
其中
X=溶剂检测植物上的活若虫数目,以及
Y=经处理的植物上的活若虫数目
结果显示在题目为“表2.桃蚜(GPA)(MYZUPE)和甘薯粉虱(WF)(BEMITA)的生物学数据”的表(参见表部分)中。
将公开的杀虫化合物对抗GPA和WF害虫的死亡率功效评级,如表1所示。
表1:桃蚜和烟粉虱的死亡率评级
%防治(或死亡率) | 评级 |
80-100 | A |
超过0-少于80 | B |
未测试 | C |
在此生物测定中未注意到活性 | D |
表2:桃蚜和甘薯粉虱的生物学数据
以下实施例用于更详细地解释本发明的实施方式。这些实施例不应当理解为对本发明范围的穷尽或排他性限制。
实施例
这些实施例出于示例说明的目的而不应该被解释为将本申请公开的发明限制为仅是在这些实施例中公开的实施方式。
商购的起始物质、试剂和溶剂无需进一步纯化即使用。无水溶剂由Aldrich以SURE/SEALTM购得且按原样使用。熔点通过ThomasHooverUnimelt毛细管熔点仪或StanfordResearchSystems中的OptiMeltAutomatedMeltingPointSystem来得到且为未校正的。使用“室温”的实施例在气候控制实验室使用约20℃至约24℃的温度进行。分子以它们的已知名称来给出,所述名称根据ISISDraw、ChemDraw或ACDNamePro中的命名程序来命名。若所述程序不能命名分子,则所述分子使用常规命名规则来命名。1HNMR波谱数据以ppm(δ)给出且在300、400或600MHz记录。13CNMR波谱数据以ppm(δ)给出,以75、100或150MHz记录。除非另有说明,19FNMR波谱数据以ppm(δ)给出且在376MHz记录。
实施例1
制备N,N-二叔丁氧基羰基(4-氯-2-(吡啶-3-yl)噻唑-5-基)胺化合物C1
在装配有加热套、回流冷凝器和氮气入口的圆底烧瓶中将N-氯琥珀酰亚胺(14.4g,108mmol)添加至N,N-二叔丁氧基羰基(2-(吡啶-3-基)噻唑-5-基)胺(如PCT申请号WO2010/129497A1中描述的进行制备)(19.0g,50.3mmol)在乙腈(MeCN,250mL)中的溶液。将混合物加热至约65℃,保持1小时。然后将混合物冷却至室温(约22℃)并减压浓缩至约20mL的体积。残余物以乙酸乙酯(EtOAc)和乙醚稀释,以饱和碳酸氢钠(NaHCO3)水溶液洗涤,经硫酸镁(MgSO4)干燥,并且然后减压浓缩得到棕色固体。固体在硅胶上纯化以己烷和EtOAc洗脱得到标题化合物(C1),为黄橙色固体(12.5g,60%)。1HNMR(400MHz,氯仿-d)δ9.12(d,J=2.2Hz,1H),8.70(dd,J=4.8,1.7Hz,1H),8.22(dt,J=8.0,2.0Hz,1H),7.43(dd,J=8.0,4.8Hz,1H),1.49(s,18H).13CNMR(101MHz,CDCl3)δ161.56,151.54,149.44,147.04,137.98,133.05,129.69,128.74,123.76,84.51,27.75.ESIMSm/z:412([M-H]-)。
实施例2
制备(4-氯-2-(吡啶-3-yl)噻唑-5-基)氨基甲酸叔丁基酯化合物C2
将TFA(25mL)添加至N,N-二叔丁氧基羰基(4-氯-2-(吡啶-3-基)噻唑-5-基)胺(C1)(10g,24.28mmol)在CH2Cl2(250mL)的溶液中。搅拌15分钟后,将反应逐份倒入含20g碳酸钠(Na2CO3)的600mL水中并剧烈搅拌10分钟。将混合物转移至分液漏斗并且分离有机层,经硫酸钠(Na2SO4)干燥,并减压浓缩得到红色固体。固体在硅胶上纯化以己烷和EtOAc洗脱得到标题化合物(C2),为米色固体(3.5g,46%收率)。1HNMR(400MHz,氯仿-d)δ9.11(d,J=2.4Hz,1H),8.63(dd,J=4.8,1.7Hz,1H),8.15(dt,J=8.0,2.0Hz,1H),7.79(s,1H),7.36(dd,J=8.0,4.8Hz,1H),1.55(s,9H).13CNMR(101MHz,CDCl3)δ153.99,152.01,150.32,146.49,132.53,129.73,129.24,123.71,123.14,83.13,28.16。ESIMSm/z310([M-H]-)。
实施例3
制备(4-氯-2-(吡啶-3-yl)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯化合物C3(方法A)
将氢化钠(60%油悬浮液,0.404g,10.1mmol)添加至(4-氯-2-(吡啶-3-基)噻唑-5-基)氨基甲酸叔丁基酯(C2)(3.00g,9.62mmol)在DMF(5mL)的冰冷溶液中。将所得棕-黄色混合物于室温搅拌10分钟并且添加3-溴丙-1-炔(1.37g,11.6mmol)。将混合物于约0℃至5℃搅拌30分钟,并除去冰浴。于室温再搅拌四小时后,将反应以饱和氯化铵(NH4Cl)水溶液淬灭并以EtOAc稀释。分离有机相,并且水相以EtOAc(3x50mL)萃取。将合并的EtOAc萃取物经MgSO4干燥,过滤,并减压浓缩得到标题化合物(C3),为棕色固体(2.78g,78%),其熔点为约74℃至76℃。1HNMR(400MHz,氯仿-d)δ9.11(d,J=2.2Hz,1H),8.69(dd,J=4.8,1.6Hz,1H),8.21(dt,J=8.0,2.0Hz,1H),7.40(dd,J=8.1,4.9Hz,1H),4.43(d,J=2.5Hz,2H),2.33(t,J=2.5Hz,1H),1.47(s,9H).ESIMSm/z350.50([M+H]+)。
实施例4
制备4-氯-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺HCl化合物C4
向(4-氯-2-(吡啶-3-基)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(C3)(2.00g,5.72mmol)在无水二噁烷(2mL)的溶液中添加4MHCl在二噁烷中的溶液(10.0mL,40.0mmol)。将干燥试管连接至烧瓶,将混合物于室温搅拌36小时。橙-黄色固体经过滤并以乙醚(10mL)接着以己烷(10mL)洗涤,并在高真空下干燥得到标题化合物(C4),为橙色固体(1.55g,90%),其熔点为大于约250℃。1HNMR(400MHz,d6-DMSO)δ9.11-8.88(m,1H),8.62(dd,J=5.2,1.5Hz,1H),8.37(ddd,J=8.1,2.3,1.4Hz,1H),7.68(ddd,J=8.1,5.2,0.8Hz,1H),4.75(bs,3.95(d,J=2.5Hz,2H),3.27(t,J=2.4Hz,1H)(未观察到NH)。ESIMSm/z:250.49([M-HCl+H]+)。
下列分子根据实施例4中描述的过程制备:
4-氯-2-(5-氟吡啶-3-基)-N-(丙-2-炔-1-基)噻唑-5-胺盐酸盐(化合物CA1)
化合物CA1分离为棕色固体(0.992g,86%):mp141-154℃;1HNMR(400MHz,DMSO-d6)δ8.82(t,J=1.6Hz,1H),8.57(d,J=2.4Hz,1H),8.03(td,J=2.8,9.8Hz,1H),6.59(bs,2H),3.99(d,J=2.4Hz,2H),3.31(t,J=2.4Hz,1H);ESIMSm/z268([M+H]+)。
4-氯-N-(丙-2-炔-1-基)-2-(嘧啶-5-基)噻唑-5-胺盐酸盐(化合物CA2)
化合物CA2分离为棕色固体(0.997g,81%):mp214-215℃;1HNMR(400MHz,DMSO-d6)δ9.16(s,1H),9.13(s,2H),6.45(bs,2H),4.00(d,J=2.4Hz,2H),3.32(t,J=2.4Hz,1H);ESIMSm/z251([M+H]+)。
实施例5
使用方法1制备N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺
化合物F7
向4-氯-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺HCl(0.120g,0.419mmol)(C4)和DMAP(0.102g,0.839mmol)在THF(3mL)的溶液中添加3-(甲硫基)丙酰氯(0.0639g,0.461mmol)。将所得混合物于50℃搅拌1小时并且以饱和NH4Cl水溶液和EtOAc稀释。分离有机相,并且水相以EtOAc(2x50mL)萃取。合并的EtOAc萃取物经MgSO4干燥,过滤,并减压浓缩,得到棕色胶状物。该胶状物在硅胶上纯化,以CH2Cl2和甲醇的混合物洗脱,得到标题化合物(F7),为淡棕色胶状物(0.077g,52%)。
下列分子根据实施例5中描述的过程(方法1)制备:
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-2-甲基-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物F9)
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-2,2-二氟-N-(丙-2-炔-1-基)环丙烷甲酰胺(化合物F5)
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-2-(甲硫基)-N-(丙-2-炔-1-基)乙酰胺(化合物F4)
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物FA1)
N-(4-氯-2-(5-氟吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物FA2)
实施例6
使用方法2制备N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-2-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺
化合物F6
向4-氯-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺HCl(C4)(0.100g,0.349mmol)、2-(甲硫基)丙酸(0.504g,0.419mmol)和DMAP(0.850mg,0.699mmol)在DMF(3mL)的溶液中添加N1-((乙亚胺基)亚甲基)-N3,N3-二甲基丙烷-1,3-二胺HCl(0.100g,0.524mmol)。将所得混合物于室温搅拌2小时。将混合物以饱和NH4Cl水溶液和EtOAc稀释。分离有机相并且水相以EtOAc(2x50mL)萃取。将合并的EtOAc萃取物经MgSO4干燥,过滤并减压浓缩,得到标题化合物,为淡棕色胶状物(0.0970g,79%)。
下列分子根据实施例6中描述的过程(方法2)制备:
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-4,4,4-三氟-3-(甲硫基)-N-(丙-2-炔-1-基)丁酰胺(化合物F3)
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)环丙烷甲酰胺(化合物F2)
N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-3-(((2,2-二氟环丙基)甲基)硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物F8)
实施例7
制备(2,4-二氯噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯化合物CA3
于0℃向(2,4-二氯噻唑-5-基)氨基甲酸叔丁基酯(如PCT申请号WO2010/129497A1描述的进行制备)(8.50g,31.6mmol)在无水DMF(100mL)的搅拌溶液中逐份添加氢化钠(NaH,60%在油中,1.51g,34.7mmol)并且搅拌混合物30分钟。向混合物中添加炔丙溴(4.47g,37.9mmol),搅拌5分钟,温热至室温,并再搅拌3小时。将反应混合物以饱和NH4Cl水溶液淬灭并以EtOAc(3×100mL)萃取。将合并的有机层以水(3×100mL)和盐水(1×100mL)洗涤,经无水Na2SO4干燥,过滤并减压浓缩得到棕色残余物。该残余物通过使用10-30%EtOAc/乙烷作为洗脱液的快速柱色谱纯化,得到标题化合物,为灰白色固体(5.80g,59%):1HNMR(400MHz,CDCl3)δ4.36(d,J=2.0Hz,2H),2.32(t,J=2.4Hz,1H),1.46(s,9H);IR(KBr)3304,2933,1681,1539,1357,1288,1219,1157cm-1;ESIMSm/z251([M+H]+)。
下列分子根据实施例7中描述的过程制备:
(2-溴-4-甲基噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(化合物CA4)
化合物CA4由(2-溴-4-甲基噻唑-5-基)氨基甲酸叔丁基酯(如PCT申请号WO2010/129497A1中描述的进行制备)合成并分离为灰白色固体(2.6g,82%):mp82-86℃;1HNMR(400MHz,CDCl3)δ4.28(s,2H),2.30(t,J=2.4Hz,1H),2.26(s,3H),1.43(s,9H);ESIMSm/z333([M+H]+)。
实施例8
制备(2-溴-4-甲基噻唑-5-基)(丁-3-炔-2-基)氨基甲酸叔丁基酯化合物CA5
于0℃在氩气气氛下向(2-溴-4-甲基噻唑-5-基)氨基甲酸叔丁基酯(0.300g,1.02mmol)在THF(5.0mL)的搅拌溶液中缓慢地添加丁-3-炔-2-醇(0.120g,2.04mmol)、三苯基膦(0.530g,2.04mmol)和二异丙基偶氮二酰亚胺(DIAD,0.410g,2.04mmol)。将反应混合物在氩气气氛下于室温搅拌16小时。将反应混合物以冷水(50mL)淬灭、减压浓缩并以EtOAc(3×50mL)萃取。将合并的有机层以盐水(2×50mL)洗涤。层经无水Na2SO4干燥,减压浓缩,并通过快速柱色谱纯化,得到标题化合物,为深棕色胶状物(0.200g,58%):1HNMR(400MHz,CDCl3)δ5.27-5.25(m,1H),2.31(d,J=2.0Hz,1H),2.23(s,3H),1.40(s,9H),1.34(d,J=7.2Hz,3H);IR(KBr)3302,3265,2980,2931,1712,1564,1477,1454,1415cm-1;ESIMSm/z345([M+H]+)。
下列化合物根据实施例8所述过程制备:
(2-溴-4-甲基噻唑-5-基)(丁-2-炔-1-基)氨基甲酸叔丁基酯(化合物CA6)
化合物CA6分离为棕色胶状物(0.20g,58%):1HNMR(400MHz,CDCl3)δ4.22(s,2H),2.24(s,3H),1.80(s,3H),1.42(s,9H);IR(KBr)2978,2922,2376,2345,2225,1716,1568,1541,1473cm-1;ESIMSm/z345([M+H]+)。
实施例9
制备(4-氯-2-(吡啶-3-基)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯化合物C3(方法B)
于室温在氮气气氛下向(2,4-二氯噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(2.00g,6.50mmol)在1,2-二甲氧基乙烷/水(4:1比例)的搅拌溶液中添加吡啶-3-基硼酸(0.958g,7.80mmol),接着添加Na2CO3(2.08g,19.5mmol)。将反应混合物以氩气吹洗;添加四(三苯基膦)钯(0)(Pd(PPh3)4,0.36g,0.32mmol),并于110℃加热5小时。将反应混合物于室温冷却,以水(50mL)稀释并以EtOAc(3×50mL)萃取。将合并的有机层以盐水(2×20mL)洗涤,经无水Na2SO4干燥并减压浓缩。粗制残余物通过使用10-100%EtOAc/己烷作为洗脱液的快速柱色谱纯化得到标题化合物,为白色固体(1.0g,44%收率):mp69-72℃;1HNMR(400MHz,CDCl3)δ9.11(d,J=2.0Hz,1H),8.69(dd,J=1.6,4.8Hz,1H),8.21(td,J=2.0,8.0Hz,1H),7.40(ddd,J=0.8,4.8,8.0Hz,1H),4.43(d,J=2.0Hz,2H),2.33(t,J=2.4Hz,1H),1.47(s,9H);ESIMSm/z350([M+H]+)。
下列分子根据实施例9中描述的过程制备:
(4-甲基-2-(吡啶-3-基)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(化合物CA7)
化合物CA7分离为棕色胶状物(1.3g,50%):1HNMR(400MHz,CDCl3)δ9.10(s,1H),8.64(t,J=1.2Hz,1H),8.26-8.18(m,1H),7.36(q,J=8.0Hz,1H),4.35(s,2H),2.36(s,3H),2.31(t,J=2.4Hz,1H),1.45(s,9H);IR(KBr)1845,1707,1589,1560,1490,1475,1384,1278cm-1;ESIMSm/z330([M+H]+)。
(2-(5-氟吡啶-3-基)-4-甲基噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯
(化合物CA8)
化合物CA8分离为灰白色固体(1.20g,67%):1HNMR(400MHz,CDCl3)δ8.89(s,1H),8.49(d,J=2.4Hz,1H),7.97-7.93(m,1H),4.35(s,2H),2.35(s,3H),2.31(t,J=2.4Hz,1H),1.45(s,9H);ESIMSm/z350([M+H]+)。
(4-氯-2-(5-氟吡啶-3-基)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(化合物CA9)
化合物CA9分离为白色固体(1.0g,42%):mp81-83℃;1HNMR(400MHz,CDCl3)δ8.90(s,1H),8.55(d,J=2.8Hz,1H),7.97(td,J=2.4,8.8Hz,1H),4.43(d,J=2.4Hz,2H),2.34(t,J=2.4Hz,1H),1.47(s,9H);ESIMSm/z368([M+H]+)。
(4-氯-2-(嘧啶-5-基)噻唑-5-基)(丙-2-炔-1-基)氨基甲酸叔丁基酯(化合物CA10)
化合物CA10分离为白色固体(1.36g,60%):mp80-83℃;1HNMR(400MHz,CDCl3)δ9.28(s,1H),9.22(s,2H),4.44(d,J=2.4Hz,2H),2.34(t,J=2.4Hz,1H),1.48(s,9H);ESIMSm/z351([M+H]+)。
丁-2-炔-1-基(4-甲基-2-(吡啶-3-基)噻唑-5-基)氨基甲酸叔丁基酯(化合物C11)
化合物CA11分离为棕色胶状物(0.45g,56%):1HNMR(400MHz,CDCl3)δ9.10(s,1H),8.64(q,J=4.8Hz,1H),8.20-8.17(m,1H),7.36(q,J=8.0Hz,1H),4.30-4.29(m,2H),2.34(s,3H),1.81(s,3H),1.44(s,9H);IR(KBr)2978,2922,2858,2306,2225,1720,1699,1556,1487cm-1;ESIMSm/z344([M+H]+)。
丁-3-炔-2-基(4-甲基-2-(吡啶-3-基)噻唑-5-基)氨基甲酸叔丁基酯(化合物CA12)
化合物CA12分离为棕色固体(0.08g,38%):mp110-123℃;1HNMR(400MHz,CDCl3)δ9.12(s,1H),8.64(q,J=4.8Hz,1H),8.22-8.19(m,1H),7.36(q,J=8.0Hz,1H),5.33-5.29(m,1H),2.35(s,1H),2.32(s,3H),1.42(s,9H),1.26(d,J=6.4Hz,3H);ESIMSm/z344([M+H]+)。
实施例10
制备N-(丁-3-炔-2-基)-4-甲基-2-(吡啶-3-基)噻唑-5-胺化合物CA13
于室温在氮气气氛下向丁-3-炔-2-基(4-甲基-2-(吡啶-3-基)噻唑-5-基)氨基甲酸叔丁基酯(0.780g,2.29mmol)在CH2Cl2(5.0mL)的溶液中添加TFA(5.0mL)。将反应混合物于室温搅拌3小时。将反应混合物减压浓缩,以NaHCO3溶液(25mL)碱化并以EtOAc(3×25mL)萃取。将合并的有机层以盐水(2×50mL)洗涤,经无水Na2SO4干燥并减压浓缩。将粗制残余物以己烷(2×25mL)研磨并真空干燥得到标题化合物,为黄色固体(0.55g,96%):ESIMSm/z244([M+H]+)。粗制物质无需进一步纯化即可用于后续反应中。
下列分子根据实施例10中公开的过程制备:
4-甲基-N-(丙-2-炔-1-基)-2-(吡啶-3-基)噻唑-5-胺(化合物CA14)
化合物CA14分离为黄色固体(0.85g,82%);ESIMSm/z230([M+H]+)。粗制物质无需进一步纯化即可用于后续反应中。
2-(5-氟吡啶-3-基)-4-甲基-N-(丙-2-炔-1-基)噻唑-5-胺(化合物CA15)
化合物CA15分离为黄色固体(0.85g,99%):ESIMSm/z250([M+H]+)。粗制物质无需进一步纯化即可用于后续反应中。
N-(丁-2-炔-1-基)-4-甲基-2-(吡啶-3-基)噻唑-5-胺(化合物CA16)
化合物CA16分离为棕色胶状物(0.60g,93%):ESIMSm/z244([M+H]+)。粗制物质无需进一步纯化即可用于后续反应中。
实施例11
制备N-(4-氯-2-(嘧啶-5-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺化合物FA3
向4-氯-N-(丙-2-炔-1-基)-2-(嘧啶-5-基)噻唑-5-胺盐酸盐(0.463g,1.85mmol)和DMAP(0.563g,4.62mmol)在1,2-二氯乙烷(15mL)的溶液中添加3-((3,3,3-三氟丙基)硫基)丙酰氯(0.814g,3.70mmol)。将所得混合物于室温搅拌16小时并以EtOAc稀释。将混合物以饱和NaHCO3水溶液和盐水洗涤,经MgSO4干燥,过滤并减压浓缩得到棕色胶状物。该胶状物通过使用EtOAc/己烷作为洗脱液的快速柱色谱纯化,得到标题化合物,为棕色固体(0.225g,28%)。
下列分子根据实施例11中描述的过程制备:
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物P1)
2-甲基-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物P2)
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物P6)
3-(((2,2-二氟环丙基)甲基)硫基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)丙酰胺(化合物P10)
N-(2-(5-氟吡啶-3-基)-4-甲基噻唑-5-基)-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物FA4)
N-(2-(5-氟吡啶-3-基)-4-甲基噻唑-5-基)-2-甲基-3-(甲硫基)-N-(丙-2-炔-1-基)丙酰胺(化合物FA5)
N-(2-(5-氟吡啶-3-基)-4-甲基噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物P19)
3-(((2,2-二氟环丙基)甲基)硫基)-N-(2-(5-氟吡啶-3-基)-4-甲基噻唑-5-基)-N-(丙-2-炔-1-基)丙酰胺(化合物P22)
N-(丁-2-炔-1-基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物P16)
N-(丁-2-炔-1-基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲硫基)丙酰胺(化合物P17)
N-(丁-2-炔-1-基)-3-(((2,2-二氟环丙基)甲基)硫基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)丙酰胺(化合物FA14)
N-(丁-3-炔-2-基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(化合物P32)
N-(丁-3-炔-2-基)-3-(((2,2-二氟环丙基)甲基)硫基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)丙酰胺(化合物P31)
实施例12
制备N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3三氟丙基)亚硫酰基)丙酰胺化合物FA6
于室温向N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(0.20g,0.46mmol)在乙酸(AcOH.2.0mL)的溶液中添加过氧硼酸钠四水合物(0.060g,0.46mmol)并搅拌3小时。将反应混合物以EtOAc(100mL)稀释,并以水(10mL)、饱和NaHCO3水溶液(2×20mL)和盐水(2×20mL)洗涤。将分离的有机层经无水Na2SO4干燥并减压浓缩。粗制残余物通过使用1-5%MeOH/CH2Cl2的快速柱色谱纯化,得到标题化合物,为棕色胶状物(0.074mg,36%)。
下列分子根据实施例12中描述的过程制备:
N-(4-氯-2-(5-氟吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)亚硫酰基)丙酰胺(化合物FA7)
N-(4-氯-2-(嘧啶-5-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)亚硫酰基)丙酰胺(化合物FA8)
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲基亚硫酰基)-N-(丙-2-炔-1-基)丙酰胺(化合物P3)
2-甲基-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲基亚硫酰基)-N-(丙-2-炔-1-基)丙酰胺(化合物P5)
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)亚硫酰基)丙酰胺(化合物P7)
3-(((2,2-二氟环丙基)甲基)亚硫酰基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)丙酰胺(化合物FA9)
实施例13
制备N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)磺酰基)丙酰胺化合物FA10
于室温向N-(4-氯-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)硫基)丙酰胺(0.187g,0.430mmol)在AcOH(2.0mL)的搅拌溶液中添加过氧硼酸钠四水合物(0.139g,1.07mmol)并于60℃搅拌3小时。将反应混合物以EtOAc(100mL)稀释,以水(1×10mL)、饱和NaHCO3水溶液(2×20mL)和盐水(1×20mL)洗涤。将分离的有机层经无水Na2SO4干燥并减压浓缩。将粗制残余物通过使用10-50%EtOAc/己烷作为洗脱液的快速柱色谱纯化,得到标题化合物,为淡棕色固体(0.0520g,23%)。
下列分子根据实施例13中公开的过程制备:
N-(4-氯-2-(5-氟吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)磺酰基)丙酰胺(化合物FA11)
N-(4-氯-2-(嘧啶-5-基)噻唑-5-基)-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)磺酰基)丙酰胺(化合物FA12)
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-3-(甲基磺酰基)-N-(丙-2-炔-1-基)丙酰胺(化合物P4)
N-(4-甲基-2-(吡啶-3-基)噻唑-5-基-N-(丙-2-炔-1-基)-3-((3,3,3-三氟丙基)磺酰基)丙酰胺(化合物P8)
3-(((2,2-二氟环丙基)甲基)磺酰基)-N-(4-甲基-2-(吡啶-3-基)噻唑-5-基)-N-(丙-2-炔-1-基)丙酰胺(化合物FA13)
表3示出了式I化合物的非限制性实例。化合物F2、F3、F6和F8根据实施例6制备。化合物F4、F5、F7、F9、FA1和FA2根据实施例5制备。化合物FA3、FA4、FA5、FA14、P1、P2、P6、P10、P19、P22、P16、P17、P32和P31根据实施例11制备。化合物FA6、FA7、FA8、FA9、P3、P5和P7根据实施例12制备。化合物FA10、FA11、FA12、FA13、P4和P8根据实施例13制备。
表3
表4示出了式I化合物的其它非限制性实例。
表4
表5显示了式I化合物的其它非限制性实例。
表5
尽管已经在某些实施方式中描述了本发明,但是本发明可以在本申请公开内容的精神和范围内进行进一步修改。因此,本申请意在涵盖本发明使用其一般原理的任何变型、用途、或改编。此外,本申请意在涵盖下述这种对本申请公开内容的偏离,即,其是本发明所属领域已知或惯用实践范围内的并且其落入所附权利要求的限定内。
Claims (44)
1.杀虫组合物,包含式I化合物或其任何农业上可接受的盐:
其中
(a)R1、R2和R4独立地为氢、F、Cl、Br、I、取代或未取代的C1-C6烷基、或取代或未取代的C1-C6卤代烷基、或取代或未取代的C1-C10环烷基、取代或未取代的C1-C10卤代环烷基,
其中所述R1、R2和R4当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C3-C10环烷基或C3-C10卤代环烷基,其各自可以为经取代的并且可以任选取代有R10:
(b)R3为氢、F、Cl、Br、I、CN、NO2、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C2-C6炔基、取代或未取代的C1-C6烷氧基、取代或未取代的C3-C10环烷基、取代或未取代的C1-C6卤代烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、OR10、C(=X1)R10、C(=X1)OR10、C(=X1)N(R10)2、N(R10)2、N(R10)C(=X1)R10、S(O)nR10、S(O)nOR10或R10S(O)nR10,
其中所述R3当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基,C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基或C1-C20杂环基,其各自为未取代的、经取代的、或取代有R10;
(c)R5选自氢,F、Cl、Br、I、CN、NO2、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、C3-C10环烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、OR10、C(=X1)R10、C(=X1)OR10、C(=X1)N(R10)2、N(R10)2、N(R10)C(=X1)R10、SR10、S(O)nOR10或R10S(O)nR10,
其中所述R5当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基或C1-C20杂环基,其各自为未取代的、经取代的、或取代有R10;
(d)Y为键或为取代或未取代的C1-C6烷基,或取代或未取代的C2-C6烯基,其中,除了Y为键的情况,其中Y当被取代时各自具有一个或多个选自以下的取代基:氢、F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基或C3-C10环烷基;任选地,Y和R7可以以环状排列连接,其中任选地这样的排列在连接Y和R7的环状结构中具有一个或多个选自以下的杂原子:O、S或N;
(e)R6选自氢,取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C2-C6炔基、取代或未取代的C3-C10环烷基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、C1-C6烷基-(C3-C10卤代环烷基),其中所述烷基和卤代环烷基独立地为取代或未取代的、或其中烷基和环烷基独立地为取代的或未取代的C1-C6烷基-(C3-C10环烷基),
其中R6当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C1-C6烷氧基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OR10、S(O)nOR10、C6-C20芳基、C1-C20杂环基或R10芳基,其各自为未取代的、经取代的或取代有R10;
(f)R7为R9、R8S(O)nR9;
(g)R8为取代或未取代的C1-C12烯基或C1-C12炔基、取代或未取代的C1-C12烷基、或取代或未取代的C3-C10环烷基,
其中所述R8当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、OR10、S(O)nR10、C6-C20芳基、或C1-C20杂环基,其各自为未取代的、经取代的或取代有R10;
(h)R9选自氢、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、取代或未取代的C3-C10环烷基、取代或未取代的C3-C10卤代环烷基、取代或未取代的C3-C10环烯基、取代或未取代的C1-C6卤代烷基、取代或未取代的C6-C20芳基、或者取代或未取代的C1-C20杂环基,
其中所述R9当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、氧代基团、OR10、S(O)nR10、C6-C20芳基或C1-C20杂环基,其各自为未取代的、经取代的或者取代有R10;
(i)R10选自氢、CN、取代或未取代的C1-C6烷基、取代或未取代的C2-C6烯基、取代或未取代的C1-C6烷氧基、取代或未取代的C2-C6烯氧基、取代或未取代的C3-C10环烷基、取代或未取代的C3-C10环烯基、取代或未取代的C6-C20芳基、取代或未取代的C1-C20杂环基、取代或未取代的S(O)nC1-C6烷基、或取代或未取代的N(C1-C6烷基)2,R8为取代或未取代的C1-C12烯基、取代或未取代的C1-C12烷基或取代或未取代的C3-C10环烷基,
其中所述R10当被取代时各自具有一个或多个选自以下的取代基:F、Cl、Br、I、CN、NO2、C1-C6烷基、C2-C6烯基、C1-C6卤代烷基、C2-C6卤代烯基、C1-C6卤代烷氧基、C2-C6卤代烯氧基、C3-C10环烷基、C3-C10环烯基、C3-C10卤代环烷基、C3-C10卤代环烯基、OC1-C6烷基、OC1-C6卤代烷基、S(O)nC1-C6烷基、S(O)nOC1-C6烷基、C6-C20芳基或C1-C20杂环基;
(j)Q和X1独立地为氧(O)或硫(S);
(k)n为0、1或2;和
(l)Z为N或C-R3。
2.权利要求1的组合物,其中R1、R2和R4为氢。
3.权利要求1的组合物,其中R3为氢、F、Cl、Br或I。
4.权利要求1的组合物,其中R3为氢或F。
5.权利要求1的组合物,其中R5选自F、Cl、Br、I或未取代的C1-C6烷基。
6.权利要求1的组合物,其中R5为Cl或CH3。
7.权利要求1的组合物,其中Y-C≡C-R6为CH2C≡CH或CH(CH3)C≡CH。
8.权利要求1的组合物,其中R7为(C1-C6)烷基-S(O)n-(C1-C6)烷基、(C1-C6)烷基-S(O)n-(C1-C6)卤代烷基或(C1-C6)烷基-S(O)n-(C1-C6)烷基-(C3-C6)卤代环烷基。
9.权利要求1的组合物,其中Q和X1独立地为氧(O)。
10.权利要求1的组合物,其中n为0或1。
11.权利要求1的组合物,其中Z为C-R3。
12.权利要求1的组合物,其还包含:
(a)一种或者多种具有杀螨、杀藻、杀害鸟、杀菌、杀真菌、除草、杀昆虫、杀软体动物、杀线虫、杀啮齿动物,或者杀病毒性质的化合物;或者
(b)一种或者多种作为抗饲育剂、驱鸟剂、化学绝育剂、除草剂安全剂、昆虫引诱剂、昆虫驱避剂、哺乳动物驱避剂、交配扰乱剂、植物活化剂、植物生长调节剂,或者协同剂的化合物;或者
(c)(a)和(b)二者。
13.权利要求1的组合物,其还包含一种或多种选自以下的化合物:(3-乙氧基丙基)溴化汞、1,2-二氯丙烷、1,3-二氯丙烯、1-甲基环丙烯、1-萘酚、2-(辛基硫基)乙醇、2,3,5-三-碘苯甲酸、草芽平、草芽平-二甲铵、草芽平-锂、草芽平-钾、草芽平-钠、2,4,5-涕、2,4,5-涕-2-丁氧基丙基、2,4,5-涕-2-乙基己基、2,4,5-涕-3-丁氧基丙基、2,4,5-涕丁酸、2,4,5-涕-丁氧基丙酯、2,4,5-涕-丁氧乙酯、2,4,5-涕-丁基、2,4,5-涕-异丁基、2,4,5-涕-异辛酯、2,4,5-涕-异丙基、2,4,5-涕-甲基、2,4,5-涕-戊基、2,4,5-涕-钠、2,4,5-涕-三乙铵、2,4,5-涕-三乙醇胺、2,4-滴、2,4-滴-2-丁氧基丙基、2,4-滴-2-乙基己基、2,4-滴-3-丁氧基丙基、2,4-滴-铵、2,4-滴丁酸、2,4-滴丁酸-丁基、2,4-滴丁酸-二甲铵、2,4-滴丁酸-异辛酯、2,4-滴丁酸-钾、2,4-滴丁酸-钠、2,4-滴-丁氧乙酯、2,4-滴-丁基、2,4-滴-二乙铵、2,4-滴-二甲铵、2,4-滴-二醇胺、2,4-滴-十二烷基铵、赛信、伐草磷、2,4-滴-乙基、2,4-滴-庚基铵、2,4-滴-异丁基、2,4-滴-异辛酯、2,4-滴-异丙基、2,4-滴-异丙基铵、2,4-滴-锂、2,4-滴-甲基庚基酯、2,4-滴-甲基、2,4-滴-辛基、2,4-滴-戊基、2,4-滴-钾、2,4-滴-丙基、2,4-滴-钠、2,4-滴-糖草酯、2,4-滴-十四烷基铵、2,4-滴-三乙铵、2,4-滴-三(2-羟基丙基)铵、2,4-滴-三乙醇胺、2iP、2-甲氧基乙基氯化汞、2-苯基苯酚、3,4-滴胺、3,4-滴丁酸、3,4-滴丙酸、4-氨基吡啶、对氯苯氧乙酸、对氯苯氧乙酸-钾、对氯苯氧乙酸-钠、4-CPB、4-CPP、4-羟基苯乙醇、8-羟基硫酸喹啉、8-苯基汞氧基喹啉、阿维菌素、诱抗素、ACC、乙酰甲胺磷、灭螨醌、啶虫脒、家蝇磷、乙草胺、乙酯磷、acetoprole、活化酯、活化酯-S-甲基、三氟羧草醚、三氟羧草醚-甲基、三氟羧草醚-钠、苯草醚、acrep、氟丙菊酯、丙烯醛、丙烯腈、acypetacs、acypetacs-copper、acypetacs-zinc、甲草胺、棉铃威、丙硫多菌灵、涕灭威、烯丙菊酯、涕灭砜威、艾氏剂、烯丙菊酯、大蒜素、二丙烯草胺、阿洛氨菌素、禾草灭、禾草灭-钠、烯丙醇、除害威、五氯戊酮酸、顺式氯氰菊酯、α-硫丹、辛唑嘧菌胺、特津酮、莠灭净、特草嗪酮、氨唑草酮、拌种灵、赛硫磷、amidoflumet、酰嘧磺隆、灭害威、环丙嘧啶酸、环丙嘧啶酸-甲基、环丙嘧啶酸-钾、氯氨基吡啶酸、氯氨基吡啶酸-钾、氯氨基吡啶酸-三(2-羟基丙基)铵、甲基胺草磷、胺草磷、吲唑磺菌胺、胺吸磷、胺吸磷草酸盐、双甲脒、杀草强、氨基磺酸铵、α-萘乙酸铵、代森铵、1-氨基丙基磷酸、新烟碱、环丙嘧啶醇、敌菌灵、莎椑磷、疏草隆、蒽醌、安妥、环磷氮丙啶、杀螨特、三氧化二砷、福美砷、阿司匹林、磺草灵、磺草灵-钾、磺草灵-钠、艾噻达松、阿特拉通、莠去津、金色制酶素、aviglycine、aviglycinehydrochloride、氧环唑、印楝素、唑啶炔草、甲基吡噁磷、四唑嘧磺隆、益棉磷、保棉磷、叠氮净、塞仑、偶氮苯、三唑锡、偶氮磷、嘧菌酯、bachmedesh、燕麦灵、六氟硅酸钡、多硫化钡、熏虫菊、BCPC、氟丁酰草胺、苯霜灵、苯霜灵-M、草除灵、草除灵-二甲铵、草除灵-乙基、草除灵-钾、bencarbazone、benclothiaz、噁虫威、乙丁氟灵、丙硫克百威、呋草黄、麦锈灵、苯菌灵、解草嗪、苯噁磷、醌肟腙、苄嘧磺隆脱甲基酸、苄嘧磺隆、地散磷、杀虫磺、bentaluron、灭草松、灭草松-钠、苯噻菌胺、苯噻菌胺-异丙基、苯噻硫氰、苯草灭、胺酸杀、胺酸杀-铵、苯扎氯铵、benzamacril、benzamacril-isobutyl、benzamorf、双苯嘧草酮、苄草胺、苯并双环酮、吡草酮、氟磺胺草、苯基异羟肟酸、苯螨特、新燕灵、新燕灵-乙基、苯噻隆、苯甲酸苄酯、苄基腺嘌呤、小檗碱、盐酸小檗碱、β-氟氯氰菊酯、β-氯氰菊酯、bethoxazin、二环吡草酮、联苯肼酯、甲羧除草醚、联苯菊酯、吡氟菌酯、双丙氨酰膦、双丙氨酰膦-钠、乐杀螨、病氰硝、生物烯丙菊酯、苄呋烯菊酯、生物氯菊酯、生物苄呋菊酯、联苯、bisazir、叶枯唑、双草醚、双草醚-钠、双三氟虫脲、联苯三唑醇、硫氯酚、bixafen、灰瘟素、硼砂、波尔多液、硼酸、啶酰菌胺、芸苔素内酯、乙基芸苔素内酯、小蠹性信息素、溴鼠灵、溴灭菊酯、溴氟菊酯、除草定、除草定-锂、除草定-钠、溴敌隆、溴鼠胺、溴苄呋菊酯、溴苯烯磷、溴乙酰胺、糠草腈、溴丁酰草胺、溴烯杀、溴-滴滴涕、溴酚肟、溴硫磷、溴硫磷-乙基、溴螨酯、溴菌腈、溴苯腈、丁酰溴苯腈、庚酰溴苯腈、辛酰溴苯腈、溴苯腈-钾、溴莠敏、糠菌唑、溴硝醇、增效特、合杀威、buminafos、乙嘧酚磺酸酯、噻嗪酮、勃垦第混合液、白消安、畜虫威、丁草胺、氟丙嘧草酯、抑草磷、特嘧硫磷、丁烯草胺、苄烯菊酯、特咪唑草、丁硫啶、丁噻隆、丁酮威、丁酯膦、避蚊酮、丁酮砜威、仲丁灵、丁苯草酮、炔草隆、丁胺、丁酸盐、二甲胂酸、硫酰磷、唑草胺、砷酸钙、氯酸钙、氰氨化钙、石硫合剂、敌敌钙、克草胺酯、毒杀芬、樟脑、敌菌丹、克菌丹、吗菌威、氯灭杀威、甲萘威、卡巴草灵、多菌灵、多菌灵苯磺酸盐、多菌灵亚硫酸盐、双酰草胺、克百威、二硫化碳、四氯化碳、三硫磷、丁硫克百威、特噁唑威、环氧乙烷二氧化碳混合剂、萎锈灵、唑草酮、唑草酮-乙基、环丙酰菌胺、杀螟丹、杀螟丹盐酸盐、香芹酚、香芹酮、CDEA、叶枯炔、CEPC、ceralure、CHeshunt混合物、灭螨猛、聚氨基葡糖、灭瘟唑、甲氧除草醚、氯醛糖、草灭畏、草灭畏-铵、草灭畏-二醇胺、草灭畏-甲基、草灭畏-甲基铵、草灭畏-钠、氯胺磷、氯霉素、chloraniformethan、四氯对醌、丁酰草胺、氯虫苯甲酰胺、炔禾灵、炔禾灵-炔丙基、可乐津、杀螨醚、灭幼脲、冰片丹、氯溴隆、氯炔灵、氯丹、开蓬、杀虫脒、杀虫脒盐酸盐、氯烯炔菊酯、氯氧磷、chloreturon、伐草克、伐草克-铵、伐草克-钠、虫螨腈、氯苯咪唑、杀螨醇、燕麦酯、杀螨酯、敌螨特、毒虫畏、氟啶脲、氟嘧杀、chlorfluren、chlorfluren-methyl、整形醇、整形醇-甲基、氯草敏、氯嘧磺隆脱乙基酸、氯嘧磺隆、氯甲硫磷、氯胆碱、氯化氯胆碱、氯乙灵、草枯醚、乙酯杀螨醇、氯硝萘、氯仿、伊托明、灭虫脲、氯苯甲醚、氯鼠酮、氯敌鼠钠盐、氯化苦、三氯丙酸、丙酯杀螨醇、百菌清、氯麦隆、枯草隆、羟敌草腈、三丁氯苄膦、氯化三丁氯苄膦、氯辛硫磷、氯吡唑磷、草败死、氯苯胺灵、毒死蜱、甲基毒死蜱、四氯喹噁啉、氯磺隆、氯酞酸、氯酞酸-二甲基、氯酞酸-一甲基、氯硫酰草胺、虫螨磷、乙菌利、氯化胆碱、环虫酰胺、瓜叶菊素I、瓜叶菊素II、瓜叶菊素、吲哚酮草酯、环庚草醚、醚磺隆、ciobutide、咯草隆、左旋反灭虫菊酯、烯草酮、咪菌酮、碘氯啶酯、炔草酯、炔草酯-炔丙基、除线威、clofencet、clofencet-potassium、四螨嗪、氯贝酸、氯丁草、氯丁草-异丁基、异噁草酮、稗草胺、调果酸、环丁烯草酮、二氯吡啶酸、二氯吡啶酸-甲基、二氯吡啶酸-醇胺、二氯吡啶酸-钾、二氯吡啶酸-三(2-羟基丙基)铵、cloquintocet、解草酯(cloquintocet-mexyl)、cloransulam、氯酯磺草胺(cloransulam-methyl)、氯氰碘柳胺、噻虫胺、克霉唑、座果酸、座果酸-钠、CMA、codlelure、噻唑硫磷、乙酸铜、乙酰亚砷酸铜、砷酸铜、碱式碳酸铜、氢氧化铜、环烷酸铜、油酸铜、氯氧化铜、硅酸铜、硫酸铜、铜锌铬酸盐、氯灭鼠灵、克鼠灵、蝇毒磷、杀鼠醚、畜虫磷、coumoxystrobin、害扑威、氯胺叉草、氯丙灵、醚草敏、甲酚、鼠立死、克罗米通、巴毒磷、育畜磷、氟铝酸钠、诱蝇酮、呋菌清、苄草隆、杀菌威、氧化亚铜、莪术醇、氰胺、氰草净、氰草津、苯腈膦、杀螟腈、果虫磷、cyantraniliprole、氰霜唑、cybutryne、环菌胺、环烷基酰苯胺、环虫菊酯、环草敌、放线菌酮、环螨酯、乙氰菊酯、环丙嘧磺隆、噻草酮、环莠隆、cyenopyrafen、环氟菌胺、丁氟螨酯、氟氯氰菊酯、氰氟草酯、氰氟草酯-丁基、氯氟氰菊酯、三环锡、cymiazole、cymiazolehydrochloride、霜脲氰、解草胺腈、氰菌灵、氯氰菊酯、牧草快、氯化牧草快、苯醚氰菊酯、环丙津、三环塞草胺、环丙唑醇、嘧菌环胺、酯菌胺、环酰草胺、cyprosulfamide、灭蝇胺、畜蜱磷、香草隆、茅草枯、茅草枯-钙、茅草枯-镁、茅草枯-钠、丁酰肼、哒幼酮、棉隆、棉隆-钠、二溴氯丙烷、d-樟脑、二氯异丙醚、增产胺、滴滴涕、咪菌威、癸磷锡、一甲呋喃丹、脱氢乙酸、异丁草胺、溴氰菊酯、田乐磷、田乐磷-O、田乐磷-S、内吸磷、甲基内吸磷、内吸磷-O、内吸磷-O-甲基、内吸磷-S、内吸磷-S-甲基、砜吸磷、甜菜安、敌草净、右旋反式氯炔丙菊酯、丁醚脲、氯亚胺硫磷、燕麦敌、除线特、硅藻土、二嗪磷、邻苯二甲酸二丁酯、琥珀酸二丁酯、麦草畏、麦草畏-二甘醇胺、麦草畏-二甲铵、麦草畏-二醇胺、麦草畏-异丙基铵、麦草畏-甲基、麦草畏-醇胺、麦草畏-钾、麦草畏-钠、麦草畏-三乙醇胺、异氯磷、敌草腈、除线磷、苯氟磺胺、二氯萘醌、氯全隆、除幼脲、dichlorflurenol、dichlorflurenol-methyl、苄胺灵、烯丙酰草胺、双氯酚、2,4-滴丙酸、2,4-滴丙酸-2-乙基己基、2,4-滴丙酸-丁氧基乙酯、2,4-滴丙酸-二甲铵、2,4-滴丙酸-乙铵、2,4-滴丙酸-异辛酯、2,4-滴丙酸-甲基、精2,4-滴丙酸、精2,4-滴丙酸-2-乙基己基、精2,4-滴丙酸-二甲铵、2,4-滴丙酸-钾、2,4-滴丙酸-钠、敌敌畏、菌核利、苄氯三唑醇、双氯氰菌胺、禾草灵、禾草灵-甲基、哒菌清、哒菌清-钠、氯硝胺、唑嘧磺胺、三氯杀螨醇、双香豆素、N-(3-甲基苯基)氨基甲酸甲酯、百治磷、环虫腈、dicyclonon、狄氏剂、除螨灵、二乙除草双、二氯化二乙除草双、乙酰甲草胺、乙酰甲草胺-乙基、乙霉威、dietholate、焦碳酸二乙酯、避蚊胺、鼠得克、苯醚甲环唑、氟苯戊烯酸、氟苯戊烯酸-乙基、枯莠隆、野燕枯、野燕枯甲硫酸盐、噻鼠灵、diflovidazin、除虫脲、吡氟酰草胺、二氟吡隆、二氟吡隆-钠、氟嘧菌胺、调呋酸、调呋酸-钠、二羟丙茶碱、dimatif、四氟甲醚菊酯、甲氟磷、噁唑隆、哌草丹、菌核净、地麦威、混灭威、二甲草胺、戊草津、二甲吩草胺、精二甲吩草胺、噻节因、二甲嘧酚、乐果、烯酰吗啉、苄菊酯、驱蚊灵、邻苯二甲酸二甲酯、甲基毒虫畏、敌蝇威、敌灭生、敌米达松、醚菌胺、消螨酚、dinex-diclexine、啶菌噁唑、烯唑醇、R-烯唑醇、氨氟灵、消螨通、敌螨普、敌螨普-4、敌螨普-6、敌螨通、地乐特、硝戊酯、丙硝酚、戊硝酚、地乐酚、地乐酚乙酸盐、地乐酚-铵、地乐酚-二醇胺、地乐酚-钠、地乐酚-三乙醇胺、硝辛酯、dinotefuran、特乐酚、特乐酚乙酸盐、硝丁酯、苯虫醚、蔬果磷、二氧威、敌噁磷、敌鼠、敌鼠-钠、双苯酰草胺、二苯砜、二苯胺、地乐灵、异丙净、双硫氧吡啶、敌草快、二溴化敌草快、disparlure、2,4-滴硫钠、双硫仑、乙拌磷、2,4-滴硫钠、灭菌磷、二氰蒽醌、噻喃磷、二硫醚、氟硫草定、敌草隆、d-柠檬烯、草特磷、二硝甲酚、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、十二环吗啉、十二环吗啉乙酸盐、十二环吗啉苯甲酸盐、多地辛、多地辛盐酸盐、多地辛-钠、多果定、苯氧炔螨、dominicalure、多拉克汀、肼菌酮、甲胂钠、毒氟磷、EBEP、EBP、促蜕皮甾酮、敌瘟磷、甘草津、甘草津-乙基、甲氨基阿维菌素、甲氨基阿维菌素苯甲酸盐、多杀威、右旋烯炔菊酯、硫丹、茵多酸、茵多酸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氟嘧磺隆、烯丙苯噻唑、咪鲜胺、咪鲜胺-锰、灭螨醇、环氰津、腐霉利、氨氟乐灵、丙溴磷、氟唑草胺、环丙氟灵、profluthrin、环苯草酮、甘扑津、甘扑津-乙基、调环酸、调环酸-钙、prohydrojasmon、蜱虱威、猛杀威、扑灭通、扑草净、灭鼠肼、毒草胺、普罗帕脒、普罗帕脒二盐酸盐、霜霉威、霜霉威盐酸盐、敌稗、丙虫磷、噁草酸、快螨特、甲呋炔菊酯、扑灭津、胺丙畏、苯胺灵、丙环唑、丙森锌、异丙草胺、残杀威、丙苯磺隆、丙苯磺隆-钠、增效酯、嗪咪唑嘧磺隆、炔苯酰草胺、丙氧喹啉、补骨内酯、唑啉草酯磺亚胺草、苄草丹、氟磺隆、乙噻唑磷、硫菌威、硫菌威盐酸盐、丙硫菌唑、丙硫磷、发硫磷、protrifenbute、扑灭生、扑灭生-钠、丙炔草胺、比达农、吡蚜酮、吡喃灵、吡唑硫磷、双唑草腈、吡唑醚菌酯、吡草醚、吡草醚-乙基、嘧啶威、嘧啶威、唑胺菌酯、唑菌酯、pyrasulfotole、吡唑特、吡菌磷、吡嘧磺隆脱乙基酸、吡嘧磺隆、吡硫磷、苄草唑、反灭虫菊、除虫菊酯I、除虫菊酯II、除虫菊酯、pyribambenz-isopropyl、pyribambenz-propyl、吡菌苯威、嘧啶肟草醚、稗草丹、氯草定、哒螨灵、pyridafol、啶虫丙醚、哒嗪硫磷、哒草特、啶菌腈、啶斑肟、pyrifluquinazon、环酯草醚、嘧霉胺、嘧螨醚、嘧草醚、嘧草醚-甲基、pyrimisulfan、嘧啶磷、灭鼠优、甲氧苯啶菌、吡啶氟虫腈、吡啶醇、吡丙醚、嘧草硫醚、嘧草硫醚-钠、吡唑威、咯喹酮、pyroxasulfone、啶磺草胺、氯甲氧吡啶、氯吡呋醚、苦木、喹烯酮、喹烯酮硫酸盐、喹硫磷、喹硫磷-甲基、醌菌腙、二氯喹啉酸、氯苯喹唑、氯甲喹啉酸、灭藻醌、氯藻胺、喹塞昂、喹氧灵、喹硫磷、五氯硝基苯、喹禾灵、喹禾灵-乙基、精喹禾灵、精喹禾灵-乙基、喹禾糠酯、驱蚊酯、驱蝇啶、吡咪唑、碘醚柳胺、rebemide、苄呋菊酯、硫氰苯乙胺、闹羊花素-III、利巴韦林、砜嘧磺隆、鱼藤酮、鱼泥汀、苯嘧磺草胺、噻菌茂、赛森酮、水杨酰苯胺、血根碱、茴蒿素、八甲磷、红海葱苷、另丁津、密草通、环丙吡菌胺、赛拉菌素、单甲脒、氯化单甲脒、增效菊、芝麻啉、烯禾啶、双甲胺草磷、环草隆、siglure、灭虫硅醚、毒鼠硅、硅胶、硅噻菌胺、西玛津、硅氟唑、西玛通、西草净、杀雄啉、SMA、精异丙甲草胺、亚砷酸钠、叠氮化钠、氯酸钠、氟化钠、氟乙酸钠、六氟硅酸钠、环烷酸钠、邻苯基苯酚钠、五氯酚钠、多硫化钠、硫氰酸钠、α-萘乙酸钠、苏硫磷、乙基多杀菌素、多杀菌素、螺螨酯、螺甲螨酯、螺虫乙酯、螺噁茂胺、链霉素、链霉素倍半硫酸盐、马钱子碱、食菌甲诱醇、磺苯醚隆、磺苯醚隆-钠、磺草酮、菜草畏、甲磺草胺、舒非仑、氟虫胺、甲嘧磺隆脱甲基酸、甲嘧磺隆、磺酰磺隆、治螟磷、sulfoxaflor、亚砜、硫肟醚、硫、硫酸、硫酰氟、吖庚磺酯、硫丙磷、戊苯砜、灭草灵、τ-氟胺氰菊酯、稗草烯、噻螨威、三氯乙酸、三氯乙酸-铵、三氯乙酸-钙、TCA-ethadyl、三氯乙酸-镁、三氯乙酸-钠、滴滴滴、戊唑醇、虫酰肼、吡螨胺、异丁乙氧喹啉、嘧丙磷、牧草胺、丁噻隆、叶枯酞、四氯硝基苯、福美双联、氟苯脲、七氟菊酯、tefuryltrione、tembotrione、双硫磷、替哌、特普、吡喃草酮、环戊烯丙菊酯、特草定、特草灵、特丁草胺、特丁硫酸、甲氧去草净、特丁津、特丁净、四环唑、四氯乙烷、杀虫畏、四氟醚唑、三氯杀螨砜、氟氧隆、胺菊酯、tetramethylfluthrin、羟化四甲胺、杀螨霉素、杀螨好、硫酸亚铊、噻吩草胺、θ-氯氰菊酯、噻菌灵、噻虫啉、氟噻亚菌胺、噻虫嗪、噻丙腈、赛唑隆、噻唑烟酸、噻氯磷、噻菌腈、噻二唑胺、噻苯隆、thiencarbazone、thiencarbazone-methyl、噻吩磺隆脱甲基酸、噻吩磺隆、噻呋酰胺、禾草丹、抗虫威、硫氯苯亚胺、杀虫环、杀虫环盐酸盐、杀虫环草酸盐、噻二唑-铜、硫双威、久效威、硫氟肟醚、thiohempa、硫柳汞、甲基乙拌磷、虫线磷、硫菌灵、甲基硫菌灵、克杀螨、灭鼠特、杀虫双、杀虫双-二铵、杀虫双-二钠、杀虫单、噻替派、福美双、敌贝特、噻酰菌胺、调节安、仲草丹、嘧草胺、tioxymid、环线威、甲基立枯磷、唑虫酰胺、甲苯氟磺胺、甲苯基乙酸汞、topramezone、三甲苯草酮、溴氯氰菊酯、四溴菊酯、tralopyril、四氟苯菊酯、反氯菊酯、曲他胺、三十烷醇、三唑酮、三唑醇、triafamone、野麦畏、威菌磷、抑芽唑、苯螨噻、嘧菌醇、醚苯磺隆、唑蚜威、丁基三唑、三嗪氟草胺、三唑磷、咪唑嗪、苯磺隆脱甲基酸、苯磺隆、脱叶磷、三丁基氧化锡、杀草畏、水杨菌胺、敌百虫、异皮蝇磷、毒壤膦、绿草定、绿草定-丁氧基乙酯、绿草定-乙基、绿草定-三乙铵、三环唑、石蜡油、灭草环、草达津、杀螺吗啉、氯苯乙丙磷、肟菌酯、三氟啶磺隆、三氟啶磺隆-钠、氟菌唑、杀铃脲、氟乐灵、氟胺磺隆脱甲基酸、氟胺磺隆、三氟苯氧丙酸、三氟苯氧丙酸-甲基、三氟禾草肟、嗪氨灵、三羟基三嗪、诱蝇羧酯、混杀威、三甲隆、挺立、抗倒酯、烯虫硫酯、茚草酮、雷公藤甲素、草达克、灭菌唑、三氟甲磺隆、trunc-call、烯效唑、精烯效唑、福美甲砷、乌瑞替派、氰戊菊酯、有效霉素、valifenalate、杀鼠酮、蚜灭磷、抑霉胺、氟吡唑虫、灭草敌、乙烯菌核利、杀鼠灵、杀鼠灵-钾、杀鼠灵-钠、硝虫硫磷、辛菌胺、烯肟菌胺、灭除威、二甲苯草胺、二甲苯酚、灭杀威、抑食肼、氰菌胺、玉米素、增效胺、ζ-氯氰菊酯、环烷酸锌、磷化锌、噻唑锌、代森锌、福美锌、zolaprofos、苯酰菌胺、唑嘧磺隆、α-氯乙醇、α-蜕皮素、α-multistriatin,和α-萘乙酸。
14.权利要求1的组合物,其还包含农业上可接受的载体。
15.权利要求1的组合物,其中所述化合物为杀虫可接受的酸加成盐、盐衍生物或水合物形式。
16.权利要求1的组合物,其中所述化合物为拆分的立体异构体。
17.权利要求1的组合物,其中所述化合物为结晶多晶型物的形式。
18.权利要求1的组合物,其中所述化合物具有替代1H的2H、具有替代12C的13C、或同时具有两者。
19.权利要求1的组合物,其还包含生物杀虫剂。
20.权利要求1的组合物,其还包含以下化合物中的至少一种:
(a)3-(4-氯-2,6-二甲基苯基)-4-羟基-8-氧杂-1-氮杂螺[4,5]癸-3-烯-2-酮;
(b)3-(4’-氯-2,4-二甲基[1,1’-联苯]-3-基)-4-羟基-8-氧杂-1-氮杂螺[4,5]癸-3-烯-2-酮;
(c)4-[[(6-氯吡啶-3-基)甲基]甲基氨基]-2(5H)-呋喃酮;
(d)4-[[(6-氯吡啶-3-基)甲基]环丙基氨基]-2(5H)-呋喃酮;
(e)3-氯-N2-[(1S)-1-甲基-2-(甲基磺酰基)乙基]-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二甲酰胺;
(f)2-氰基-N-乙基-4-氟-3-甲氧基-苯磺酰胺;
(g)2-氰基-N-乙基-3-甲氧基-苯磺酰胺;
(h)2-氰基-3-二氟甲氧基-N-乙基-4-氟-苯磺酰胺;
(i)2-氰基-3-氟甲氧基-N-乙基-苯磺酰胺;
(j)2-氰基-6-氟-3-甲氧基-N,N-二甲基-苯磺酰胺;
(k)2-氰基-N-乙基-6-氟-3-甲氧基-N-甲基-苯磺酰胺;
(l)2-氰基-3-二氟甲氧基-N,N-二甲基苯磺酰胺;
(m)3-(二氟甲基)-N-[2-(3,3-二甲基丁基)苯基]-1-甲基-1H-吡唑-4-甲酰胺;
(n)N-乙基-2,2-二甲基丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙;
(o)N-乙基-2,2-二氯-1-甲基环丙烷-甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙烟碱;
(p)硫代碳酸O-{(E-)-[2-(4-氯-苯基)-2-氰基-1-(2-三氟甲基苯基)-乙烯基]}S-甲基酯;
(q)(E)-N1-[(2-氯-1,3-噻唑-5-基甲基)]-N2-氰基-N1-甲基乙脒;
(r)1-(6-氯吡啶-3-基甲基)-7-甲基-8-硝基-1,2,3,5,6,7-六氢-咪唑并[1,2-a]吡啶-5-醇;
(s)甲磺酸4-[4-氯苯基-(2-亚丁基-亚肼基)甲基)]苯基酯;和
(t)N-乙基-2,2-二氯-1-甲基环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙。
21.权利要求1的组合物,其还包含具有以下作用模式中的一种或者多种的化合物:
乙酰胆碱酯酶抑制剂;钠通道调节剂;壳多糖生物合成抑制剂;GABA和谷氨酸门控氯离子通道拮抗剂;GABA和谷氨酸门控氯离子通道激动剂;乙酰胆碱受体激动剂;乙酰胆碱受体拮抗剂;METI抑制剂;Mg刺激ATP酶抑制剂;烟碱性乙酰胆碱受体;中肠膜破裂剂;氧化磷酸化中断剂和莱恩素受体(RyRs)。
22.权利要求1的组合物,其还包含种子。
23.权利要求1的组合物,其还包含已被基因修饰以表达一种或者多种特定属性的种子。
24.权利要求1的组合物,其中所述组合物包囊在胶囊中,或者置于胶囊表面上。
25.权利要求1的组合物,其中所述组合物包囊在胶囊中,或者置于胶囊表面上,其中所述胶囊的直径为约100微米-900纳米或者约10-900微米。
26.权利要求1的组合物,其还包含硫酸铵。
27.防治害虫的方法,包括将权利要求26的组合物以足以防治害虫的量施用至防治这种害虫的区域。
28.方法,其包括将权利要求1的组合物以足以防治害虫的量施用至防治这种害虫的区域。
29.权利要求28的方法,其中所述害虫选自甲虫、蠷螋、蟑螂、蝇、蚜虫、蚧、粉虱、叶蝉、蚂蚁、黄蜂、白蚁、蛾、蝴蝶、虱、蚱蜢、蝗虫、蟋蟀、蚤、蓟马、蠹虫、螨、蜱、线虫和综合纲。
30.权利要求28的方法,其中所述害虫来自线虫门或者节肢动物门。
31.权利要求28的方法,其中所述害虫来自有螯肢亚门、多足纲,或者六足纲。
32.权利要求28的方法,其中所述害虫来自蛛形纲、综合纲,或者昆虫纲。
33.权利要求28的方法,其中所述害虫来自虱目、鞘翅目、革翅目、蜚蠊目、双翅目、半翅目、膜翅目、等翅目、鳞翅目、食毛目、直翅目、蚤目、缨翅目、缨尾目、螨目,或者综合目。
34.权利要求28的方法,其中所述害虫为桃蚜或甘薯粉虱。
35.权利要求28的方法,包括施用约0.01克/公顷至约5000克/公顷的组合物。
36.权利要求28的方法,包括施用约0.1克/公顷至约500克/公顷的组合物。
37.权利要求28的方法,包括施用约1克/公顷至约50克/公顷的组合物。
38.权利要求28的方法,其中所述防治害虫的区域为苹果、玉米、棉花、大豆、芸苔、小麦、大米、高粱、大麦、燕麦、土豆、橙子、苜蓿、莴苣、草莓、番茄、胡椒、十字花科植物、梨、烟草、杏仁、甜菜或豆类的正在生长或其种子即将播种的区域。
39.方法,其包括将权利要求1的组合物施用至已被基因修饰以表达一种或者多种特定属性的基因修饰的植物。
40.制备权利要求1的组合物的方法,所述方法包括:
使式1-1的氨基甲酸叔丁氧基酯化合物与碱反应,然后与式1-2的亲电子试剂反应,其中LG为卤素、磺酸烷基酯或磺酸芳基酯,得到式1-3的噻唑化合物;
用酸处理式1-3的噻唑化合物得到对应的式1-4的盐;和
使式1-4的盐与式1-5的酰氯(X=Cl)或羧酸(X=OH)反应,得到式I的化合物,
其中R1、R2、R4、R5、R6、R7、Y和Z如权利要求1中所定义。
41.制备权利要求1的组合物的方法,所述方法包括:
使式2-1的氨基甲酸叔丁氧基酯化合物与碱反应,然后与式2-2的亲电子试剂反应,得到式2-3的化合物;
用酸处理式2-3的化合物得到对应的式2-4的盐;和
使式2-4的盐与式2-5的酰氯反应,其中n′=1或2,得到式2-6的化合物,
其中R5、R6、n′和Z如权利要求1中所定义
42.防治害虫的方法,包括将权利要求1的杀虫组合物施用于害虫群体附近。
43.权利要求42的方法,其中所述杀虫组合物还包含植物学可接受的惰性载体。
44.权利要求42的方法,其中所述杀虫组合物还包含选自以下的添加剂:表面活性剂,稳定剂,催吐剂,崩解剂,消泡剂,润湿剂,分散剂,粘结剂,染料,和填料。
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