CN117098759A - 杂环化合物及其用途 - Google Patents
杂环化合物及其用途 Download PDFInfo
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- CN117098759A CN117098759A CN202280025220.2A CN202280025220A CN117098759A CN 117098759 A CN117098759 A CN 117098759A CN 202280025220 A CN202280025220 A CN 202280025220A CN 117098759 A CN117098759 A CN 117098759A
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- Prior art keywords
- alkyl
- group
- cycloalkyl
- substituted
- compound
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 223
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 105
- 150000003839 salts Chemical class 0.000 claims abstract description 104
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 61
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 36
- 239000004480 active ingredient Substances 0.000 claims abstract description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 23
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 125000002252 acyl group Chemical group 0.000 claims abstract description 9
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 3
- -1 or C 1 -C 6 Alkyl Chemical group 0.000 claims description 683
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 33
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 241000196324 Embryophyta Species 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000000361 pesticidal effect Effects 0.000 claims description 12
- 230000000895 acaricidal effect Effects 0.000 claims description 11
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 10
- 239000000642 acaricide Substances 0.000 claims description 9
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 9
- 239000002917 insecticide Substances 0.000 claims description 9
- 239000005645 nematicide Substances 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000009395 breeding Methods 0.000 claims description 5
- 230000006798 recombination Effects 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000002420 orchard Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000005252 haloacyl group Chemical group 0.000 claims description 3
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
- 230000000856 effect on pests Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 description 123
- 229910052751 metal Inorganic materials 0.000 description 55
- 239000002184 metal Substances 0.000 description 55
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000002904 solvent Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000002585 base Substances 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 150000001721 carbon Chemical group 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 241000320508 Pentatomidae Species 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000009472 formulation Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000003446 ligand Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 19
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 19
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 17
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 17
- 159000000000 sodium salts Chemical class 0.000 description 17
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- 241000894007 species Species 0.000 description 16
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 16
- 229960005294 triamcinolone Drugs 0.000 description 16
- 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 description 15
- 241000244206 Nematoda Species 0.000 description 15
- 241000500437 Plutella xylostella Species 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 14
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 14
- 241001529598 Colaspis Species 0.000 description 13
- 241000258937 Hemiptera Species 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 240000007594 Oryza sativa Species 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 11
- 241001124181 Bactrocera dorsalis Species 0.000 description 11
- 241000255925 Diptera Species 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
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- 239000007800 oxidant agent Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 239000005476 Bentazone Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
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- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 10
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
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- 125000004438 haloalkoxy group Chemical group 0.000 description 9
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
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- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
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- 244000269722 Thea sinensis Species 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 description 8
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 8
- 229960001231 choline Drugs 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
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- 125000006125 ethylsulfonyl group Chemical group 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
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- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- 229930183279 tetramycin Natural products 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- CENHPXAQKISCGD-UHFFFAOYSA-N trioxathietane 4,4-dioxide Chemical compound O=S1(=O)OOO1 CENHPXAQKISCGD-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241000701451 unidentified granulovirus Species 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 229940102566 valproate Drugs 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Insects & Arthropods (AREA)
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明提供具有优异的防治有害生物效果的杂环化合物或其盐、包括用其作为有效成分的有害生物防治剂以及它的制造中间体。本发明提供通式[I]表示的杂环化合物或其农药可接受的盐,和以含有其作为活性成分为特征的有害生物防治剂,其中,R1表示氢原子、氰基、或未经取代或经卤原子取代的C1‑C7酰基,R2表示C1‑C6烷基等,A1及A2各自独立地表示氮原子、CH或键,W1或W2之一表示氮原子,另一个表示碳原子,A3、A4、A5、A6、A7、A8及A9各自独立地表示氮原子或分别经R3、R4、R5、R6、R7、R8及R9取代的碳原子,R3、R4、R5、R6、R7、R8及R9各自表示氢原子、C1‑C6卤代烷基等,R10表示氢原子、C1‑C12烷基、C1‑C6烷氧基C1‑C6烷基、C1‑C12卤代烷基等,且R11表示卤原子、叠氮基、氰基等。
Description
技术领域
本发明是关于含有新的杂环化合物或其盐、衍生物或其盐作为有效成分的有害生物防治剂,及其生产中间体。
背景技术
专利文献1公开了具有杀虫活性的化合物。
专利文献2公开了具有杀虫活性且与单环基团耦合的化合物。
专利文献3公开了具有杀虫活性且通过氮-碳键与单环基团耦合的化合物。
专利文献4公开了具有杀虫活性的二芳基唑化合物。
专利文献5公开了具有杀虫活性的烷氧基吡唑化合物。
专利文献6公开了在通过氮-碳键结合的含氮五元环相邻的位置上结合含硫取代基的稠环化合物。然而,并没有关于杀虫活性的公开。
在上述专利文献中,并未公开本发明的杂环化合物。
现有技术文献
专利文献
1.国际专利公开号2017/061497
2.国际专利公开号2018/052119
3.国际专利公开号2019/124548
4.国际专利公开号2016/204270
5.日本专利公开号2021-024859
6.国际专利公开号03/048081
发明内容
本发明解决的技术问题
期望可用于有用作物的有害生物防治剂是在施用于土壤或树叶时可以低剂量表现出足够的有害生物防治效果的药剂。此外,由于对化学物质的安全性及其对环境影响的要求越来越高,因此期待开发出更安全的有害生物防治剂。此外,近年来,由于长期使用杀昆虫剂、杀螨剂及杀线虫剂等有害生物防治剂,出现了对有害生物防治剂产生抗药性的有害生物。因此,变得难以完全控制有害生物。此外,使用对人和动物具有高毒性的有害生物防治剂对于操作者安全等方面也是一个问题。
本发明的课题在于解决现有有害生物防治剂存在的上述问题,进而提供具有优异的安全性、防治效果、残留效果等的有害生物防治剂以及用于该目的的新的化合物。
用于解决问题的手段
为了开发具有上述较好特性的有害生物防治剂,本发明人合成了各种杂环化合物并且深入地研究了它们的生理活性。结果发现,由下述通式[I]表示的杂环化合物(以下,也称为本发明化合物)对各种有害生物具有优异的防治效果。本发明人进一步研究从而完成了本发明。
也就是,本发明是关于以下的发明。
(1)通式[I]表示的化合物或其盐,
式中,m及n各自独立地表示0、1或2的整数,且其总和为0至2的整数,R1表示氢原子、氰基或未经取代或经卤原子取代的C1-C7酰基,
R2表示C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、氰基C1-C6烷基、氰基C3-C6环烷基、未经取代或任选经R11取代的C7-C14芳烷基、或未经取代或任选经R11取代的C6-C14杂芳烷基,
W1表示氮原子,
W2表示碳原子,或
W1表示碳原子,
W2表示氮原子,
A1表示氮原子、经Ra取代的碳原子、或键,
A2表示氮原子、经Rb取代的碳原子、或键,
A3表示氮原子、经R3取代的碳原子、或键,
A1、A2或A3的任一者为键,
A4、A5、A6、A7、A8及A9各自独立地表示氮原子、或分别经R4、R5、R6、R7、R8及R9取代的碳原子,
Ra、Rb、R3、R4、R5、R6、R7、R8及R9各自独立地表示氢原子、卤原子、叠氮基、氰基、硝基、C1-C6烷基、氰基C1-C6烷基、羟基C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、氰基C3-C6环烷基、羟基C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烯基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、C3-C6环烷基C2-C6烯基、C3-C6环烷基C2-C6炔基、未经取代或任选经R11取代的杂环基、未经取代或任选经R11取代的C6-C12芳基、未经取代或任选经R11取代的C5-C12杂芳基、未经取代或任选经R11取代的C7-C14芳烷基、未经取代或任选经R11取代的C6-C14杂芳烷基、羟基、C1-C6烷氧基、C1-C6卤代烷氧基、氰基C1-C6烷氧基、羟基C1-C6烷氧基、C1-C6卤代烷氧基C1-C6烷氧基、C1-C6烷氧基C1-C6卤代烷氧基、C1-C6卤代烷氧基C1-C6卤代烷氧基、C3-C6环烷氧基、C3-C6环烷基C1-C6烷氧基、C3-C6卤代环烷氧基、氰基C3-C6环烷氧基、C3-C6卤代环烷基C1-C6烷氧基、(氰基C3-C6环烷基)C1-C6烷氧基、C1-C6卤代烷基硫基C1-C6烷氧基、C1-C6卤代烷基亚磺酰基C1-C6烷氧基、C1-C6卤代烷基磺酰基C1-C6烷氧基、未经取代或任选经R11取代的C7-C14芳烷氧基、未经取代或任选经R11取代的C6-C14杂芳烷氧基、未经取代或任选经R11取代的C6-C12芳氧基、未经取代或任选经R11取代的C5-C12杂芳氧基、硫烷基、五卤代硫烷基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C3-C6环烷基硫基、C3-C6环烷基亚磺酰基、C3-C6环烷基磺酰基、C3-C6卤代环烷基硫基、C3-C6卤代环烷基亚磺酰基、C3-C6卤代环烷基磺酰基、C3-C6环烷基C1-C6烷基硫基、C3-C6环烷基C1-C6烷基亚磺酰基、C3-C6环烷基C1-C6烷基磺酰基、C3-C6卤代环烷基C1-C6烷基硫基、C3-C6卤代环烷基C1-C6烷基亚磺酰基、C3-C6卤代环烷基C1-C6烷基磺酰基、基团-S(R12)=NH、基团-S(R12)=N-C≡N、基团-S(R12)=N-C(=O)R13、基团-S(R12)(=O)=NH、基团-S(R12)(=O)=N-C≡N、基团-S(R12)(=O)=N-C(=O)R13、C6-C12芳基硫基、C6-C12芳基亚磺酰基、C6-C12芳基磺酰基、C5-C12杂芳基硫基、C5-C12杂芳基亚磺酰基、C5-C12杂芳基磺酰基、氨基、单(C1-C6烷基)氨基、二(C1-C6烷基)氨基、(二(C1-C6烷基)亚磺酰亚基)氨基、二(C1-C6烷基)磷酰基、C1-C7酰基、C1-C7卤酰基、羟基亚氨基C1-C6烷基、羟基亚氨基(氨基)C1-C7烷基、C1-C6烷氧基亚氨基C1-C6烷基、C1-C6卤代烷氧基亚氨基C1-C6烷基、羧基、C1-C6烷氧基羰基、氨基羰基、单(C1-C6烷基)氨基羰基、二(C1-C6烷基)氨基羰基、单(C1-C6卤代烷基)氨基羰基、单(C3-C6环烷基)氨基羰基、单(氰基C3-C6环烷基)氨基羰基、单(C1-C6烷氧基亚氨基C1-C6烷基)氨基羰基、二(C1-C6烷基)氨基亚甲基氨基羰基、氨基硫羰基、单(C1-C6烷基)氨基硫羰基、二(C1-C6烷基)氨基硫羰基、或N-(C1-C6烷氧基)-N-(C1-C6烷基)氨基羰基,
R10表示氢原子、C1-C12烷基、C1-C6烷氧基C1-C6烷基、C1-C12卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C3-C6环烷基C2-C6炔基、C2-C6卤代炔基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、未经取代或任选经R11取代的杂环基C1-C6烷基、未经取代或任选经R11取代的C7-C14芳烷基、未经取代或任选经R11取代的C6-C14杂芳烷基、未经取代或任选经R11取代的C6-C12芳基、或未经取代或任选经R11取代的C5-C12杂芳基,
R11表示卤原子、叠氮基、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、五卤代硫烷基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、氨基、单(C1-C6烷基)氨基,或二(C1-C6烷基)氨基,及
R12及R13独立地表示C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、氰基C1-C6烷基、未经取代或任选经R11取代的C7-C14芳烷基、或未经取代或任选经R11取代的C6-C14杂芳烷基。
(2)根据上述(1)的化合物或其盐,其中A7表示氮原子,且A8及A9各自表示分别经R8及R9取代的碳原子。
(3)根据上述(1)的化合物或其盐,其中A1表示键,且A2及A7各自表示氮原子,
W1表示氮原子,
W2表示碳原子,
A3、A4、A5、A6、A8及A9各自表示分别经R3、R4、R5、R6、R8及R9取代的碳原子。
(4)根据上述(3)的化合物或其盐,其中R3、R4、R5、R6、R8及R9各自独立地表示氢原子、卤原子、C1-C6烷基、C1-C6卤代烷基、氰基C3-C6环烷基、C1-C6卤代烷氧基或氰基C1-C6烷氧基。
(5)根据上述(1)至(4)中任一项的化合物或其盐,其中R2表示C1-C6烷基。
(6)根据上述(1)至(5)中任一项的化合物或其盐,其中R10表示C1-C12卤代烷基。
(7)根据上述(1)的化合物或其盐,其中该通式[I]表示的化合物为通式[Ia]表示的化合物,其中
式中,A2、A3、A4、A5、A6、A7、A8、A9、m、n、R1、R2及R10具有如上述(1)中相同的定义。
(8)根据上述(1)的化合物或其盐,其中该通式[I]表示的化合物为通式[A]表示的化合物,
式中,n、R3、R4、R5、R6及R10具有如上述(1)中相同的定义。
(9)根据上述(8)的化合物或其盐,其中n为2,R3、R5及R6各自为氢原子,R4为C1-C6卤代烷基、氰基C3-C6环烷基、C1-C6卤代烷氧基、或氰基C1-C6烷氧基,且R10为C1-C12卤代烷基。
(10)根据上述(1)的化合物或其盐,其中该通式[I]表示的化合物为通式[B]表示的化合物,
式中,R2、R4、R5及R10具有如上述(1)中相同的定义。
(11)根据上述(1)的化合物或其盐,其中该通式[I]表示的化合物为通式[C]表示的化合物,
式中,m、n、R1、R4、R5及R10具有如上述(1)中相同的定义。
(12)根据上述(1)的化合物或其盐,其中该通式[I]表示的化合物为通式[D]表示的化合物,
式中,A2、A3、A4、A5、A6及R10具有如上述(1)中相同的定义。
(13)根据上述(12)的化合物或其盐,其中A2表示氮原子或经Rb取代的碳原子,A3表示氮原子或经R3取代的碳原子,且A4、A5及A6各自独立地表示氮原子或分别经R4、R5及R6取代的碳原子。
(14)一种农药组合物,其含有根据上述(1)至(13)中任一项的化合物或其盐作为有效成分。
(15)根据上述(14)的农药组合物,其中该农药组合物进一步含有表面活性剂。
(16)一种有害生物防治剂,其含有根据上述(1)至(13)中任一项的化合物或其盐作为活性成分。
(17)根据上述(16)的有害生物防治剂,其中该有害生物防治剂为杀昆虫剂、杀线虫剂及杀螨剂。
(18)根据上述(17)的有害生物防治剂,其对于在种植农业及园艺植物的水田、农地、草坪、果园、非农用地、温室、苗圃设施、植物工厂中的有害生物具有防治效果。
(19)根据上述(18)的有害生物防治剂,其中该农业及园艺植物是通过育种方法或基因重组技术已被赋予抗性的植物。
(20)一种防治有害生物的方法,其使用有效量的根据上述(1)至(13)中任一项的化合物或其盐。
(21)一种防治有害生物的方法,其通过将含有上述(1)至(13)中任一项的化合物或其盐作为有效成分的农药组合物同时或分次地作用于将种植或正在种植农作物或园艺作物的场所。
(22)根据上述(20)或(21)的防治有害生物的方法,其中该有害生物防治剂施用的场所为水田、农地、草坪、果园、非农用地、温室、苗圃设施或植物工厂。
(23)根据上述(20)至(22)的防治有害生物的方法,其中使用上述(1)至(13)中任一项的化合物或其盐用作为杀昆虫剂、杀线虫剂或杀螨剂使用。
(24)根据上述(16)至(19)中任一项的有害生物防治剂用于防治针对农作物或园艺作物的有害生物的用途。
(25)根据上述(1)的通式[I]表示的化合物或其盐,其中在通式[I]中的R10为氢原子。
(26)一种制造上述(1)的通式[I]表示的化合物的方法,包括使用上述(25)的化合物或其盐作为原料。
本发明的效果
含有本发明化合物的有害生物防治剂对于广范围的有害生物呈现优异的防治效果,所述有害生物例如对于半翅目害虫、鳞翅目害虫、鞘翅目害虫、双翅目害虫、膜翅目害虫、直翅目害虫、等翅目害虫、樱翅目害虫、螨类、和植物寄生性线虫,且也可防治已获得抗药性的有害生物。
具体实施方式
说明本文所描述的符号及术语。
在本发明中,“有害生物防治剂”是指用于农业或园艺领域及例如牲畜及宠物的动物的家庭及防疫用的杀虫剂、杀线虫剂或杀螨剂。
在本发明中,“卤原子”是指氟原子、氯原子、溴原子及碘原子。
在本发明中,例如“C1-C6”的符号表明元素符号后面的数字表示碳原子数。例如,在这种情况下,碳原子数可在1至6的范围。
在本发明中,“C1-C2烷基”是指具有1至2个碳原子的直键烷基,除非另有说明。例如,可举出甲基及乙基等。
在本发明中,“C1-C6烷基”是指具有1至6个碳原子的直键或支键烷基,除非另有说明。例如,除了上述“C1-C2烷基”中的实例外,还可举出正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、新戊基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1-乙基丁基、2-乙基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基等。
在本发明中,“C1-C12烷基”是指具有1至12个碳原子的直键或支键烷基,除非另有说明。例如,除了上述“C1-C6烷基”中的实例外,还可举出庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、异庚基、1,1-二甲基戊基、2,2-二甲基戊基、4,4-二甲基戊基、1-乙基戊基、2-乙基戊基、1,1,3-三甲基丁基、1,2,2-三甲基丁基、1,3,3-三甲基丁基、2,2,3-三甲基丁基、2,3,3-三甲基丁基、1-丙基丁基、1,1,2,2-四甲基丙基、辛基、1-甲基庚基、3-甲基庚基、异辛基、2-乙基己基、5,5-二甲基己基、2,4,4-三甲基戊基、1-乙基-1-甲基戊基、1-丙基戊基、壬基、1-甲基辛基、2-甲基辛基、3-甲基辛基、异壬基、1-乙基庚基、1,1-二甲基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、2-甲基壬基、6-甲基壬基、异癸基、1-乙基辛基、1-丙基庚基、十一基、1-甲基癸基、异十一基、十二基、1-甲基十一基、异十二基等。
在本发明中,“C1-C6卤代烷基”是指具有经1至13个相同或不同的卤原子取代的1至6个碳原子的直键或支键烷基,除非另有说明。例如,可举出氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、碘甲基、氯二氟甲基、二氯氟甲基、1-氟乙基、2-氟乙基、1,1-二氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基、五氟乙基、1-氯乙基、2-氯乙基、1,1-二氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1,1,2,2-四氯乙基、五氯乙基、1-溴乙基、2-溴乙基、2,2,2-三溴乙基、1-碘乙基、2-碘乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2-三氯乙基、1-氟丙基、2-氟丙基、3-氟丙基、1,1-二氟丙基、2,2-二氟丙基、3,3-二氟丙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-氟丙-2-基、2-氟丙-2-基、1,1-二氟丙-2-基、1,2-二氟丙-2-基、1,3-二氟丙-2-基、1,2,3-三氟丙-2-基、1,1,3,3-四氟丙-2-基、1,1,1,3,3,3-六氟丙-2-基、七氟丙-2-基、1-氯丙基、2-氯丙基、3-氯丙基、1,1-二氯丙基、2,2-二氯丙基、3,3-二氯丙基、3,3,3-三氯丙基、2,2,3,3,3-五氯丙基、七氯丙基、1-氯丙-2-基、2-氯丙-2-基、1,1-二氯丙-2-基、1,2-二氯丙-2-基、1,3-二氯丙-2-基、1,2,3-三氯丙-2-基、1,1,3,3-四氯丙-2-基、1,1,1,3,3,3-六氯丙-2-基、七氯丙-2-基、1-溴丙基、2-溴丙基、3-溴丙基、1-溴丙-2-基、2-溴丙-2-基、1-碘丙基、2-碘丙基、3-碘丙基、1-碘丙-2-基、2-碘丙-2-基、1-氟丁基、2-氟丁基、3-氟丁基、4-氟丁基、4,4-二氟丁基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、九氟丁基、1,1,1-三氟丁-2-基、4,4,4-三氟丁-2-基、3,3,4,4,4-五氟丁-2-基、九氟丁-2-基、1,1,1,3,3,3-六氟-2-(三氟甲基)丙-2-基、1-氯丁基、2-氯丁基、3-氯丁基、4-氯丁基、4,4-二氯丁基、4,4,4-三氯丁基、九氯丁基、1,1,1-三氯丁-2-基、4,4,4-三氯丁-2-基、九氯丁-2-基、1-溴丁基、2-溴丁基、3-溴丁基、4-溴丁基、1-碘丁基、2-碘丁基、3-碘丁基、4-碘丁基、4-氯-1,1,2,2,3,3,4,4-八氟丁基、4-溴-1,1,2,2,3,3,4,4-八氟丁基、1-氟戊基、2-氟戊基、3-氟戊基、4-氟戊基、5-氟戊基、5,5,5-三氟戊基、4,4,5,5,5-五氟戊基、3,3,4,4,5,5,5-七氟戊基、2,2,3,3,4,4,5,5,5-九氟戊基、十一氟戊基、1-氯戊基、2-氯戊基、3-氯戊基、4-氯戊基、5-氯戊基、5,5,5-三氯戊基、4,4,5,5,5-五氯戊基、3,3,4,4,5,5,5-七氯戊基、2,2,3,3,4,4,5,5,5-九氯戊基、十一氯戊基、1-溴戊基、2-溴戊基、3-溴戊基、4-溴戊基、5-溴戊基、5-碘戊基、1-氟己基、2-氟己基、3-氟己基、4-氟己基、5-氟己基、6-氟己基、6,6,6-三氟己基、5,5,6,6,6-五氟己基、4,4,5,5,6,6,6-七氟己基、3,3,4,4,5,5,6,6,6-九氟己基、2,2,3,3,4,4,5,5,6,6,6-十一氟己基、十三氟己基、1-氯己基、2-氯己基、3-氯己基、4-氯己基、5-氯己基、6-氯己基、5-溴己基、6-溴己基、5-碘己基或6-碘己基等。
在本发明中,“C1-C12卤代烷基”是指具有经1至25个相同或不同的卤原子取代的1至12个碳原子的直键或支键烷基,除非另有说明。例如,除了上述“C1-C6卤代烷基”中的实例外,还可举出2,2,3,4,4,6,6,6-八氟-3,5,5-三(三氟甲基)己基、1H,1H-全氟庚基、1H,1H,2H,2H-全氟庚基、1H,1H,2H,2H,3H,3H-全氟庚基、1H,1H,7H-全氟庚基、全氟庚基、2-(全氟-3-甲基丁基)乙基、1H,1H-全氟辛基、1H,1H,2H,2H-全氟辛基、1H,1H,2H,2H,3H,3H-全氟辛基、6-(全氟己基)乙基、1H,1H,8H-全氟辛基、全氟辛基、1H,1H-全氟壬基、1H,1H,2H,2H-全氟壬基、1H,1H,2H,2H,3H,3H-全氟壬基、6-(全氟-1-甲基乙基)己基、1H,1H,9H-全氟壬基、全氟壬基、1H,1H-全氟癸基、1H,1H,2H,2H-全氟癸基、1H,1H,2H,2H,3H,3H-全氟癸基、6-(全氟丁基)己基、1H,1H,9H-全氟癸基或全氟癸基等。
在本发明中,“C3-C6环烷基”是指具有3至6个碳原子的环烷基,除非另有说明。例如,可举出环丙基、环丁基、环戊基及环己基等。
在本发明中,“C3-C6卤代环烷基”是指具有经1至11个相同或不同的卤原子取代的3至6个碳原子的环烷基,除非另有说明。例如,可举出1-氟环丙基、2-氟环丙基、2,2-二氟环丙基、2,2,3,3-四氟环丙基、1-氯环丙基、2-氯环丙基、2,2-二氯环丙基、2,2,3,3-四氯环丙基、2,2-二溴环丙基、2,2-二碘环丙基、1-氟环丁基、2-氟环丁基、3-氟环丁基、3,3-二氟环丁基、七氟环丁基、2-氯环丁基、3-氯环丁基、3,3-二氯环丁基、3,3-二溴环丁基、3,3-二碘环丁基、1-氟环戊基、2-氟环戊基、3-氟环戊基、2,2-二氟环戊基、3,3-二氟环戊基、九氟环戊基、2,2-二氯环戊基、3,3-二氯环戊基、2,2-二溴环戊基、3,3-二溴环戊基、2,2-二碘环戊基、3,3-二碘环戊基、1-氟环己基、2-氟环己基、3-氟环己基、4-氟环己基、2,2-二氟环己基、3,3-二氟环己基、4,4-二氟环己基、1-氯环己基、2-氯环己基、3-氯环己基、4-氯环己基、2,2-二氯环己基、3,3-二氯环己基、4,4-二氯环己基、3,3-二溴环己基、4,4-二溴环己基、3,3-二碘环己基、4,4-二碘环己基或全氟环己基等。
在本发明中,“C2-C6烯基”是指具有2至6个碳原子的直键或支键烯基,除非另有说明。例如,可举出乙烯基、1-丙烯基、异丙烯基、2-丙烯基、1-丁烯基、1-甲基-1-丙烯基、2-丁烯基、1-甲基-2-丙烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1,3-丁二烯基、1-戊烯基、1-乙基-2-丙烯基、2-戊烯基、1-甲基-1-丁烯基、3-戊烯基、1-甲基-2-丁烯基、4-戊烯基、1-甲基-3-丁烯基、3-甲基-1-丁烯基、1,2-二甲基-2-丙烯基、1,1-二甲基-2-丙烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1,2-二甲基-1-丙烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,3-戊二烯基、1-乙烯基-2-丙烯基、1-己烯基、1-丙基-2-丙烯基、2-己烯基、1-甲基-1-戊烯基、1-乙基-2-丁烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-4-戊烯基、1-乙基-3-丁烯基、1-(异丁基)乙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-2-丙烯基、1-(异丙基)-2-丙烯基、2-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1,3-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1,5-己二烯基、1-乙烯基-3-丁烯基、2,4-己二烯基或3,3-二甲基-1-丁烯基等。
在本发明中,“C2-C6卤代烯基”是指具有经1至11个相同或不同的卤原子取代的2至6个碳原子的直键或支键烯基,除非另有说明。例如,可举出1-氟乙烯基、2-氟乙烯基、1,2-二氟乙烯基、2,2-二氟乙烯基、三氟乙烯基、1-氯乙烯基、2-氯乙烯基、1,2-二氯乙烯基、2,2-二氯乙烯基、三氯乙烯基、1,2-二溴乙烯基、2,2-二溴乙烯基、三溴乙烯基、1,2-二碘乙烯基、2,2-二碘乙烯基、三碘乙烯基、1-氟-2-丙烯基、2-氟-2-丙烯基、3-氟-2-丙烯基、2,3-二氟-2-丙烯基、3,3-二氟-2-丙烯基、3,3-二氟-1-丙烯基、2,3,3-三氟-2-丙烯基、3,3,3-三氟-1-丙烯基、2-氯-3,3,3-三氟-1-丙烯基、1,2,3,3,3-五氟-1-丙烯基、1-氯-2-丙烯基、2-氯-2-丙烯基、3-氯-2-丙烯基、2,3-二氯-2-丙烯基、3,3-二氯-2-丙烯基、3,3-二氯-1-丙烯基、2,3,3-三氯-2-丙烯基、3,3,3-三氯-1-丙烯基、3-溴-2-丙烯基、3,3-二溴-2-丙烯基、3,3-二碘-2-丙烯基、2,2-二氟-1-丙烯-2-基、3,3,3-三氟-1-丙烯-2-基、3,3,3-三氯-1-丙烯-2-基、4-氟-3-丁烯基、4,4-二氟-3-丁烯基、4,4-二氟-3-丁烯-2-基、4,4,4-三氟-2-丁烯基、3,4,4-三氟-3-丁烯基、2-三氟甲基-2-丙烯基、2-三氟甲基-3,3-二氟-2-丙烯基、4,4,4-三氟-3-氯-2-丁烯基、4,4-二氯-3-丁烯基、4,4,4-三氯-2-丁烯基、2-三氯甲基-2-丙烯基、5,5-二氟-4-戊烯基、4,5,5-三氟-4-戊烯基、5,5,5-三氟-3-戊烯基、4,4,4-三氟-3-甲基-2-丁烯基、4,4,4-三氟-3-三氟甲基-2-丁烯基、5,5-二氯-4-戊烯基、4,4,4-三氯-3-甲基-2-丁烯基、6,6-二氟-5-己烯基、5,6,6-三氟-5-戊烯基、6,6,6-三氟-4-戊烯基、5,5,5-三氟-4-甲基-3-戊烯基、5,5,5-三氟-4-三氟甲基-3-戊烯基、6,6-二氯-5-己烯基或5,5,5-三氯-4-甲基-3-戊烯基等。
在本发明中,“C3-C6环烯基”是指具有3至6个碳原子的环烯基,除非另有说明。例如,可举出1-环丙烯-1-基、1-环丁烯-1-基、1-环戊烯-1-基或1-环己烯-1-基等。
在本发明中,“C2-C6炔基”是指具有2至6个碳原子的直键或支键炔基,除非另有说明。例如,可举出乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、1-甲基-2-丙炔基、2-丁炔基、3-丁炔基、1-戊炔基、1-乙基-2-丙炔基、2-戊炔基、3-戊炔基、1-甲基-2-丁炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-己炔基、1-(正丙基)-2-丙炔基、2-己炔基、1-乙基-2-丁炔基、3-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基、5-己炔基、1-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基、1-(异丙基)-2-丙炔基、1,1-二甲基-2-丁炔基、或2,2-二甲基-3-丁炔基或3,3-二甲基-1-丁炔基等。
在本发明中,“C2-C6卤代炔基”是指具有经1至9个相同或不同的卤原子取代的2至6个碳原子的直键或支键炔基,除非另有说明。例如,可举出氟乙炔基、氯乙炔基、溴乙炔基、碘乙炔基、3-氟-2-丙炔基、3-氯-2-丙炔基、3-溴-2-丙炔基、3-碘-2-丙炔基、4-氟-3-丁炔基、4-氯-3-丁炔基、4-溴-3-丁炔基、4-碘-3-丁炔基、4,4-二氟-2-丁炔基、4,4-二氯-2-丁炔基、4,4,4-三氟-2-丁炔基、4,4,4-三氯-2-丁炔基、3-氟-1-甲基-2-丙炔基、3-氯-1-甲基-2-丙炔基、5-氟-4-戊炔基、5-氯-4-戊炔基、5,5,5-三氟-3-戊炔基、5,5,5-三氯-3-戊炔基、4-氟-2-甲基-3-丁炔基、4-氯-2-甲基-3-丁炔基、6-氟-5-己炔基、6-氯-5-己炔基、6,6,6-三氟-4-己炔基、6,6,6-三氯-4-己炔基、5-氟-3-甲基-4-戊炔基或5-氯-3-甲基-4-戊炔基等。
在本发明中,“C3-C6环烷基C2-C6炔基”是指其中C2-C6炔基的任何位置被C3-C6环烷基取代的基团,其中该环烷基部分及该炔基部分具有上述定义,除非另有说明。例如,可举出环丙基乙炔基、环丁基乙炔基、环戊基乙炔基、环己基乙炔基、3-环丙基-1-丙炔基、1-环丙基-2-丙炔基、3-环丙基-2-丙炔基、3-环丙基-1,1-二甲基-2-丙炔基、4-环丙基-1,1-二甲基-2-丁炔基等。
在本发明中,“C1-C6烷氧基”是指(C1-C6烷基)-O-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1-乙基丙氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基或正己氧基等。
在本发明中,“C1-C6卤代烷氧基”是指(C1-C6卤代烷基)-O-基团,其中该卤代烷基部分具有上述定义,除非另有说明。例如,可举出二氟甲氧基、二氯甲氧基、三氟甲氧基、三氯甲氧基、三溴甲氧基、氯二氟甲氧基、溴二氟甲氧基、2-氟乙氧基、1-氯乙氧基、2-氯乙氧基、1-溴乙氧基、2-溴乙氧基、2,2-二氟乙氧基、1,2-二氯乙氧基、2,2-二氯乙氧基、2,2,2-三氟乙氧基、2,2,2-三氯乙氧基、1,1,2,2-四氟乙氧基、五氟乙氧基、2-溴-2-氯乙氧基、2-氯-1,1,2,2-四氟乙氧基、1-氯-1,2,2,2-四氟乙氧基、1-氯丙氧基、2-氯丙氧基、3-氯丙氧基、2-溴丙氧基、3-溴丙氧基、2-溴-1-甲基乙氧基、3-碘丙氧基、2,3-二氯丙氧基、2,3-二溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氟-2-丙氧基、3,3,3-三氯丙氧基、3-溴-3,3-二氟丙氧基、2,2-二氟丙氧基、3,3-二氯-3-氟丙氧基、2,2,3,3-四氟丙氧基、1-溴-3,3,3-三氟丙氧基、2,2,3,3,3-五氟丙氧基、2,2,2-三氟-1-三氟甲基乙氧基、七氟丙氧基、七氟-2-丙氧基、1,2,2,2-四氟-1-三氟甲基乙氧基、1,1,2,3,3,3-六氟丙氧基、2-氯丁氧基、3-氯丁氧基、4-氯丁氧基、2-氯-1,1-二甲基乙氧基、4-溴丁氧基、3-溴-2-甲基丙氧基、2-溴-1,1-二甲基乙氧基、2,2-二氯-1,1-二甲基乙氧基、2-氯-1-氯甲基-2-甲基乙氧基、4,4,4-三氟丁氧基、3,3,3-三氟-1-甲基丙氧基、3,3,3-三氟-2-甲基丙氧基、2,3,4-三氯丁氧基、2,2,2-三氯-1,1-二甲基乙氧基、4-氯-4,4-二氟丁氧基、4,4-二氯-4-氟丁氧基、4-溴-4,4-二氟丁氧基、2,4-二溴-4,4-二氟丁氧基、3,4-二氯-3,4,4-三氟丁氧基、3,3-二氯-4,4,4-三氟丁氧基、4-溴-3,3,4,4-四氟丁氧基、4-溴-3-氯-3,4,4-三氟丁氧基、2,2,3,3,4,4-六氟丁氧基、2,2,3,4,4,4-六氟丁氧基、2,2,2-三氟-1-甲基-1-三氟甲基乙氧基、3,3,3-三氟-2-三氟甲基丙氧基、2,2,3,3,4,4,4-七氟丁氧基、3,3,4,4,4-五氟-2-丁氧基、2,3,3,3-四氟-2-三氟甲基丙氧基、1,1,2,2,3,3,4,4-八氟丁氧基、九氟丁氧基、全氟-叔丁氧基、4-氯-1,1,2,2,3,3,4,4-八氟丁氧基、5,5,5-三氟戊氧基、4,4,5,5,5-五氟戊氧基、3,3,4,4,5,55-七氟戊氧基、3,3,4,4,5,5,5-七氟-2-戊氧基、2,2,3,3,4,4,5,5,5-九氟戊氧基、2,2,3,3,4,4,5,5-八氟戊氧基、全氟戊氧基、4,4,5,5,5-五氟-2-丁氧基、2,2-双(三氟甲基)丙氧基、2,2,3,3,4,4,5,5,6,6,6-十一氟己氧基、3,3,4,4,5,5,6,6,6-九氟己氧基、4,4,5,5,6,6,6-七氟己氧基、2,2,3,3,4,4,5,5,6,6-十氟己氧基、4,4,4-三氟-3,3-双(三氟甲基)丁氧基、全氟己氧基等。
在本发明中,“C1-C6烷氧基C1-C6烷基”是指其中C1-C6烷基的任何位置被C1-C6烷氧基取代的基团,其中该烷氧基部分及烷基部分具有上述定义,除非另有说明。例如,可举出甲氧基甲基、乙氧基甲基、正丙氧基甲基、异丙氧基甲基、叔丁氧基甲基、1-甲氧基乙基、1-甲氧基-1-甲基乙基、2-甲氧基乙基、1-乙氧基乙基、2-乙氧基乙基、2-异丙氧基乙基、3-甲氧基丙基、2-甲氧基丙基、3-乙氧基丙基、4-甲氧基丁基或4-乙氧基丁基等。
在本发明中,“C1-C6烷氧基C1-C6卤代烷基”是指其中C1-C6卤代烷基的任何位置被C1-C6烷氧基取代的基团,其中该烷氧基部分及卤代烷基部分具有上述定义,除非另有说明。例如,可举出由上述“C1-C6烷氧基”及“C1-C6卤代烷基”示例的那些基团的任意组合。
在本发明中,“C1-C6卤代烷氧基C1-C6烷基”是指其中C1-C6烷基的任何位置被C1-C6卤代烷氧基取代的基团,其中该卤代烷氧基部分及该烷基部分具有上述定义,除非另有说明。例如,可举出由上述“C1-C6卤代烷氧基”及“C1-C6烷基”示例的那些基团的任意组合。
在本发明中,“C1-C6卤代烷氧基C1-C6卤代烷基”是指其中C1-C6卤代烷基的任何位置被C1-C6卤代烷氧基取代的基团,其中该卤代烷氧基部分及该卤代烷基部分具有上述定义,除非另有说明。例如,可举出由上述“C1-C6卤代烷氧基”及“C1-C6卤代烷基”示例的那些基团的任意组合。
在本发明中,”C3-C6环烷基C1-C6烷基”是指其中C1-C6烷基的任何位置被C3-C6环烷基取代的基团,其中该环烷氧基部分及该烷基部分具有上述定义,除非另有说明。例如,可举出由上述“C3-C6环烷基”及“C1-C6烷基”示例的那些基团的任意组合。
在本发明中,“C3-C6卤代环烷基C1-C6烷基”是指其中C1-C6烷基的任何位置被C3-C6卤代环烷基取代的基团,其中该卤代环烷基部分及该烷基部分具有上述定义,除非另有说明。例如,可举出由上述“C3-C6卤代环烷基”及“C1-C6烷基”示例的那些基团的任意组合。
在本发明中,“C3-C6环烷基C2-C6烯基”是指其中C2-C6烯基的任何位置被C3-C6环烷基取代的基团,其中该环烷基部分及该烯基部分具有上述定义,除非另有说明。例如,可举出由上述“C3-C6环烷基”及“C2-C6烯基”示例的那些基团的任意组合。
在本发明中,“C1-C6卤代烷氧基C1-C6烷氧基”是指其中C1-C6烷氧基的任何位置被C1-C6卤代烷氧基取代的基团,其中该卤代烷氧基部分及该烷氧基部分具有上述定义,除非另有说明。例如,可举出由上述“C1-C6卤代烷氧基”及“C1-C6卤代烷基”示例的那些基团的任意组合。
在本发明中,“C1-C6烷氧基C1-C6卤代烷氧基”是指其中C1-C6卤代烷氧基的任何位置被C1-C6烷氧基取代的基团,其中该烷氧基部分及该卤代烷氧基部分,除非另有说明。例如,可举出由上述“C1-C6烷氧基”及“C1-C6卤代烷氧基”示例的那些基团的任意组合。
在本发明中,“C1-C6卤代烷氧基C1-C6卤代烷氧基”是指其中C1-C6卤代烷氧基的任何位置被C1-C6卤代烷氧基取代的基团,其中该卤代烷氧基部分具有上述定义,除非另有说明。例如,可举出由上述“C1-C6卤代烷氧基”示例的那些基团的任意组合。该C1-C6卤代烷氧基可彼此相同或不同。
在本发明中,“C3-C6环烷氧基”是指(C3-C6环烷基)-O-基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出环丙氧基、环丁氧基、环戊氧基或环己氧基等。
在本发明中,“C3-C6卤代环烷氧基”是指(C3-C6卤代环烷基)-O-基团,其中该卤代环烷基部分具有上述定义,除非另有说明。例如,可举出2,2-二氟环丙氧基、2,2-二氯环丙氧基、3,3-二氟环丁氧基、3,3-二氯环丁氧基、3-氟环戊氧基、3,3-二氟环戊氧基、九氟环戊氧基、3,3-二氯环戊氧基、4,4-二氟环己氧基或4,4-二氯环己氧基等。
在本发明中,“C3-C6环烷基C1-C6烷氧基”是指其中C1-C6烷氧基的任何位置被C3-C6环烷基取代的基团,其中该环烷氧基部分及该烷氧基部分具有上述定义,除非另有说明。例如,可举出环丙基甲氧基、环丁基甲氧基、环戊基甲氧基或环己基甲氧基。
在本发明中,“C3-C6卤代环烷基C1-C6烷氧基”是指其中C1-C6烷氧基的任何位置被C3-C6卤代环烷基取代的基团,其中该卤代环烷基部分及该烷氧基部分具有上述定义,除非另有说明。例如,可举出1-氟环丙基甲氧基、1-氯环丙基甲氧基、1-溴环丙基甲氧基、1-氟环丁基甲氧基、1-氯环丁基甲氧基、1-溴环丁基甲氧基、2,2-二氟环丙基甲氧基、2,2-二氯环丙基甲氧基、及3,3-二氟环丁基甲氧基。
在本发明中,“C6-C12芳基”是指具有6至12个碳原子的芳基,除非另有说明。例如,可举出苯基、1-萘基及2-萘基。1-萘基也称为萘-1-基。2-萘基也称为萘-2-基。
在本发明中,“C6-C12芳氧基”是指(C6-C12芳基)-O-基团,除非另有说明。例如,可举出苯氧基、萘-1-基氧基、萘-2-基氧基等。
在本发明中,“C7-C14芳烷基”是指经具有7至14个碳原子的芳基取代的烷基,除非另有说明。例如,可举出C6-C12芳基C1-C2烷基、苯基C1-C2烷基等。C7-C14芳烷基的具体实例包括苄基、1-苯基乙基、2-苯基乙基、3-苯基丙基、4-苯基丁基、萘-1-基甲基、萘-2-基甲基等。此外,芳烷基也称为芳基烷基。
在本发明中,“C7-C14芳烷氧基”是指(C7-C14芳烷基)-O-基团,其中该芳烷基部分具有上述定义,除非另有说明。例如,可举出芐氧基、1-苯基乙氧基、2-苯基乙氧基、3-苯基丙氧基、4-苯基丁氧基、(萘-1-基)甲氧基、(萘-2-基)甲氧基等。
在本发明中,“C5-C12杂芳基”是指具有5至12个碳原子形成的单环或稠合双环结构,其具有一个或多个选自O、S及N的杂原子。包括杂原子使得在5元环及6元环中具有芳族性。典型杂原子系统的实例包括单环C5-C6芳族基团,例如吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噻吩基、呋喃基、吡咯基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、咪唑基、三唑基、噻二唑基、噁二唑基或四唑基;可举出通过这些单环基团中的一个与苯环或与任何杂芳单环基团稠合形成C8-C10双环基团的稠合双环部分,例如吲哚基、苯并咪唑基、吲唑基、苯并三唑基、异喹啉基、喹啉基、苯并噻唑基、苯并呋喃基、苯并噻吩基、苯并异噁唑基、吡唑并吡啶基、喹唑啉基、喹噁啉基或啉基等。
对此,取代位置并没有特别限制。即,杂芳基包括其所有位置的异构体。例如,当杂芳基为吡啶基时,吡啶基可为2-吡啶基、3-吡啶基或4-吡啶基。
在本发明中,“C5-C12杂芳氧基”是指(C5-C12杂芳基)-O-基团,其中该杂芳基部分具有上述定义,除非另有说明。
在本发明中,“C6-C14杂芳烷基”是指其中C1-C2烷基的任何位置被具有5至12个碳原子的杂芳基取代的烷基,其中该杂芳基部分具有上述定义,且该C1-C2烷基部分是指甲基或乙基,除非另有说明。例如,可举出吡啶基甲基、吡啶基乙基、吲哚基甲基、呋喃基甲基、噻吩基甲基、吡咯基甲基等。
在本发明中,“C6-C14杂芳烷氧基”是指(C6-C14杂芳烷基)-O-基团,其中该杂芳烷基部分具有上述定义,除非另有说明。例如,可举出吡啶基甲氧基、吡啶基乙氧基、吲哚基甲氧基、呋喃基甲氧基、噻吩基甲氧基、吡咯基甲基、吡咯基甲氧基等。
在本发明中,“五卤代硫烷基”是指经5个相同或不同卤原子取代的λ6-硫烷基,除非另有说明。例如,可举出氯四氟硫烷基或五氟硫烷基等。
在本发明中,“C1-C6烷基硫基”是指(C1-C6烷基)-S-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基、戊基硫基或己基硫基等。
在本发明中,“C1-C6烷基亚磺酰基”是指(C1-C6烷基)-S(=O)-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、戊基亚磺酰基或己基亚磺酰基等。
在本发明中,“C1-C6烷基磺酰基”是指(C1-C6烷基)-S(=O)2-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、戊基磺酰基或己基磺酰基等。
在本发明中,“C1-C6卤代烷基硫基”是指(C1-C6卤代烷基)-S-基团,其中该卤代烷基部分具有上述定义,除非另有说明。例如,可举出氟甲基硫基、二氟甲基硫基、三氟甲基硫基、三氯甲基硫基、2,2,2-三氟乙基硫基、五氟乙基硫基、2,2,2-三氯乙基硫基、3,3,3-三氟丙基硫基、1,1,2,3,3,3-六氟丙基硫基、七氟丙基硫基、(1,1,1,3,3,3-六氟丙-2-基)硫基、(七氟丙-2-基)硫基或4,4,4-三氟丁基硫基等。
在本发明中,“C1-C6卤代烷基亚磺酰基”是指(C1-C6卤代烷基)-S(=O)-基团,其中该卤代烷基部分具有上述定义,除非另有说明。例如,可举出二氟甲基亚磺酰基、三氟甲基亚磺酰基、三氯甲基亚磺酰基、2,2,2-三氟乙基亚磺酰基、2,2,2-三氯乙基亚磺酰基、五氟乙基亚磺酰基、3,3,3-三氟丙基亚磺酰基、七氟丙基亚磺酰基或七氟-2-丙基亚磺酰基等。
在本发明中,“C1-C6卤代烷基磺酰基”是指(C1-C6卤代烷基)-S(=O)2-基团,其中该卤代烷基部分具有上述定义,除非另有说明。例如,可举出二氟甲基磺酰基、三氟甲基磺酰基、三氯甲基磺酰基、2,2,2-三氟乙基磺酰基、五氟乙基磺酰基、3,3,3-三氟丙基磺酰基、七氟丙基磺酰基、七氟-2-丙基磺酰基或九氟丁基磺酰基等。
在本发明中,“C3-C6环烷基硫基”是指(C3-C6环烷基)-S-基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出环丙基硫基、环丁基硫基、环戊基硫基或环己基硫基等。
在本发明中,“C3-C6环烷基亚磺酰基”是指(C3-C6环烷基)-S(=O)-基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出环丙基亚磺酰基、环丁基亚磺酰基、环戊基亚磺酰基或环己基亚磺酰基等。
在本发明中,“C3-C6环烷基磺酰基”是指(C3-C6环烷基)-S(=O)2-基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出环丙基磺酰基、环丁基磺酰基、环戊基磺酰基或环己基磺酰基等。
在本发明中,“C3-C6卤代环烷基硫基”是指(C3-C6卤代环烷基)-S-基团,其中该卤代环烷基部分具有上述定义,除非另有说明。例如,可举出2,2-二氟环丙基硫基、2,2-二氯环丙基硫基、3,3-二氟环丁基硫基、3,3-二氯环丁基硫基、3-氟环戊基硫基、3,3-二氟环戊基硫基、九氟环戊基硫基、3,3-二氯环戊基硫基、4,4-二氟环己基硫基或4,4-二氯环己基硫基等。
在本发明中,“C3-C6卤代环烷基亚磺酰基”是指(C3-C6卤代环烷基)-S(=O)-基团,其中该卤代环烷基部分具有上述定义,除非另有说明。例如,可举出2,2-二氟环丙基亚磺酰基、2,2-二氯环丙基亚磺酰基、3,3-二氟环丁基亚磺酰基、3,3-二氯环丁基亚磺酰基、3-氟环戊基亚磺酰基、3,3-二氟环戊基亚磺酰基、九氟环戊基亚磺酰基、3,3-二氯环戊基亚磺酰基、4,4-二氟环己基亚磺酰基或4,4-二氯环己基亚磺酰基等。
在本发明中,“C3-C6卤代环烷基磺酰基”是指(C3-C6卤代环烷基)-S(=O)2-基团,其中该卤代环烷基部分具有上述定义,除非另有说明。例如,可举出2,2-二氟环丙基磺酰基、2,2-二氯环丙基磺酰基、3,3-二氟环丁基磺酰基、3,3-二氯环丁基磺酰基、3-氟环戊基磺酰基、3,3-二氟环戊基磺酰基、九氟环戊基磺酰基、3,3-二氯环戊基磺酰基、4,4-二氟环己基磺酰基或4,4-二氯环己基磺酰基等。
在本发明中,“C1-C6烷基磺酰氧基“是指(C1-C6烷基磺酰基)-O-基团,其中该烷基磺酰基部分具有上述定义,除非另有说明。例如,可举出甲基磺酰氧基、乙基磺酰氧基、正丙基磺酰氧基、异丙基磺酰氧基、正丁基磺酰氧基、异丁基磺酰氧基、仲丁基磺酰氧基、叔丁基磺酰氧基、戊基磺酰氧基或己基磺酰氧基等。
在本发明中,“C1-C6卤代烷基磺酰氧基”是指(C1-C6卤代烷基磺酰基)-O-基团,其中该卤代烷基磺酰基部分具有上述定义,除非另有说明。例如,二氟甲基磺酰氧基、三氟甲基磺酰氧基、三氯甲基磺酰氧基、2,2,2-三氟乙基磺酰氧基、五氟乙基磺酰氧基、3,3,3-三氟丙基磺酰氧基、七氟丙基磺酰氧基、七氟-2-丙基磺酰氧基或九氟丁基磺酰氧基等。
在本发明中,“C6-C12芳基硫基”是指(C6-C12芳基)-S-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出苯基硫基、1-萘基硫基、2-萘基硫基等。
在本发明中,“C6-C12芳基亚磺酰基”是指(C6-C12芳基)-S(=O)-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出苯基亚磺酰基、1-萘基亚磺酰基、2-萘基亚磺酰基等。
在本发明中,“C6-C12芳基磺酰基”是指(C6-C12芳基)-S(=O)2-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出苯基磺酰基、1-萘基磺酰基、2-萘基磺酰基等。
在本发明中,“C5-C12杂芳基硫基”是指(C5-C12杂芳基)-S-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出吡啶-2-基硫基、吡啶-3-基硫基、吡啶-4-基硫基、吡嗪-2-基硫基、哒嗪-3-基硫基、哒嗪-4-基硫基、嘧啶-2-基硫基、嘧啶-4-基硫基、嘧啶-5-基硫基、噻唑-2-基硫基、噻唑-4-基硫基或噻唑-5-基硫基等。
在本发明中,“C5-C12杂芳基亚磺酰基”是指(C5-C12杂芳基)-S(=O)-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出吡啶-2-基亚磺酰基、吡啶-3-基亚磺酰基、吡啶-4-基亚磺酰基、吡嗪-2-基亚磺酰基、哒嗪-3-基亚磺酰基、哒嗪-4-基亚磺酰基、嘧啶-2-基亚磺酰基、嘧啶-4-基亚磺酰基、嘧啶-5-基亚磺酰基、噻唑-2-基亚磺酰基、噻唑-4-基亚磺酰基或噻唑-5-基亚磺酰基等。
在本发明中,“C5-C12杂芳基磺酰基”是指(C5-C12杂芳基)-S(=O)2-基团,其中该芳基部分具有上述定义,除非另有说明。例如,可举出吡啶-2-基磺酰基、吡啶-3-基磺酰基、吡啶-4-基磺酰基、吡嗪-2-基磺酰基、哒嗪-3-基磺酰基、哒嗪-4-基磺酰基、嘧啶-2-基磺酰基、嘧啶-4-基磺酰基、嘧啶-5-基磺酰基、噻唑-2-基磺酰基、噻唑-4-基磺酰基或噻唑-5-基磺酰基等。
在本发明中,“C6-C12芳基磺酰氧基”是指(C6-C12芳基磺酰基)-O-基团,其中该芳基磺酰基部分具有上述定义,除非另有说明。例如,可举出苯基磺酰氧基、1-萘基磺酰氧基、2-萘基磺酰氧基等。
在本发明中,“C1-C6卤代烷基硫基C1-C6烷氧基”是指其中该C1-C6烷氧基的任何位置被C1-C6卤代烷基硫基取代的基团,其中该卤代烷基硫基部分及该烷氧基部分具有上述定义,除非另有说明。
在本发明中,“C1-C6卤代烷基亚磺酰基C1-C6烷氧基”是指其中该C1-C6烷氧基的任何位置被C1-C6卤代烷基亚磺酰基取代的基团,其中该卤代烷基亚磺酰基部分及烷氧基部分具有上述定义,除非另有说明。
在本发明中,“C1-C6卤代烷基磺酰基C1-C6烷氧基”是指其中该C1-C6烷氧基的任何位置被C1-C6卤代烷基磺酰基取代的基团,其中该卤代烷基磺酰基部分及烷氧基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6环烷基C1-C6烷基硫基”是指其中该C1-C6烷基硫基的任何位置被C3-C6环烷基取代的基团,其中该环烷基部分及该烷基硫基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6环烷基C1-C6烷基亚磺酰基”是指其中该C1-C6烷基亚磺酰基的任何位置被C3-C6环烷基取代的基团,其中该环烷基部分及该烷基亚磺酰基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6环烷基C1-C6烷基磺酰基”是指其中该C1-C6烷基磺酰基的任何位置被C3-C6环烷基取代的基团,其中该环烷基部分及该烷基磺酰基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6卤代环烷基C1-C6烷基硫基”是指其中该C1-C6烷基硫基的任何位置被C3-C6卤代环烷基取代的基团,其中该卤代环烷基部分及该烷基硫基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6卤代环烷基C1-C6烷基亚磺酰基”是指其中该C1-C6烷基亚磺酰基的任何位置被C3-C6卤代环烷基取代的基团,其中该卤代环烷基部分及该烷基亚磺酰基部分具有上述定义,除非另有说明。
在本发明中,“C3-C6卤代环烷基C1-C6烷基磺酰基”是指其中该C1-C6烷基磺酰基的任何位置被C3-C6卤代环烷基取代的基团,其中该卤代环烷基部分及该烷基磺酰基部分具有上述定义,除非另有说明。
在本发明中,“羟基C1-C6烷氧基”是指其中该烷氧基的任何位置被“HO-”取代的基团。
在本发明中,“羟基C3-C6环烷氧基”是指其中该环烷氧基的任何位置被“HO-”取代的基团。
在本发明中,“羟基亚氨基C1-C6烷基”是指其中该烷基的任何位置被“HO-N=”取代的基团。
在本发明中,“C1-C6烷氧基亚氨基C1-C6烷基”是指其中该烷基的任何位置被“(C1-C6烷氧基)-N=”取代的基团。
在本发明中,“C1-C6卤代烷氧基亚氨基C1-C6烷基”是指其中该烷基的任何位置被“(C1-C6卤代烷氧基)-N=”取代的基团。
在本发明中,“氰基C1-C6烷基”是指其中该C1-C6烷基的任何位置被氰基取代的基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出氰基甲基、1-氰基乙基、2-氰基乙基、3-氰基丙基、2-氰基丙-2-基、1-氰基丁基、4-氰基丁基、5-氰基戊基或6-氰基己基等。
在本发明中,“氰基C3-C6环烷基”是指其中该C3-C6环烷基的任何位置被氰基取代的基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出1-氰基环丙基、2-氰基环丙基、1-氰基环丁基、2-氰基环丁基、3-氰基环丁基、1-氰基环戊基、3-氰基环戊基、1-氰基环己基或4-氰基环己基等。
在本发明中,“羟基C1-C6烷基”是指其中该C1-C6烷基的任何位置被羟基取代的基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出羟基甲基、1-羟乙基、2-羟乙基、3-羟基丙基、2-羟基丙烷-2-基、1-羟基丁基、4-羟基丁基、5-羟基戊基或6-羟基己基等。
在本发明中,“羟基C3-C6环烷基”是指其中该环烷基的任何位置被羟基取代的基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出1-羟基环丙基、2-羟基环丙基、1-羟基环丁基、2-羟基环丁基、3-羟基环丁基、1-羟基环戊基、3-羟基环戊基、1-羟基环己基或4-羟基环己基等。
在本发明中,“氰基C3-C6环烷氧基”是指其中该C3-C6环烷氧基的任何位置被氰基取代的基团,其中该环烷氧基部分具有上述定义,除非另有说明。例如,可举出1-氰基环丙氧基、2-氰基环丙氧基、1-氰基环丁氧基、2-氰基环丁氧基、3-氰基环丁氧基、1-氰基环戊氧基、3-氰基环戊氧基、1-氰基环己氧基或4-氰基环己氧基等。
在本发明中,“氰基C1-C6烷氧基”是指其中该C1-C6烷氧基的任何位置被氰基取代的基团,其中该烷氧基部分具有上述定义,除非另有说明。例如,可举出氰基甲氧基、1-氰基乙氧基、2-氰基乙氧基、1-氰基丙氧基、3-氰基丙氧基、2-氰基-2-丙氧基、1-氰基丁氧基、4-氰基丁氧基、5-氰基戊氧基或6-氰基己氧基等。
在本发明中,“(氰基C3-C6环烷基)C1-C6烷氧基”是指其中该C1-C6烷氧基的任何位置被氰基C3-C6环烷基取代的基团,其中该氰基C3-C6环烷基部分及该烷氧基部分具有上述定义,除非另有说明。例如,可举出(1-氰基环丙基)甲氧基、(2-氰基环丙基)甲氧基、(1-氰基环丁基)甲氧基、(2-氰基环丁基)甲氧基、(3-氰基环丁基)甲氧基、(1-氰基环戊基)甲氧基、(3-氰基环戊基)甲氧基、(1-氰基环己基)甲氧基或(4-氰基环己基)甲氧基等。
在本发明中,“单(C1-C6烷基)氨基”是指(C1-C6烷基)-NH-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲基氨基、乙基氨基、异丙基氨基、正丙基氨基或叔丁基氨基等。
在本发明中,“二(C1-C6烷基)氨基”是指(C1-C6烷基)2-N-基团,其中该烷基部分具有上述定义,且该二个烷基可彼此不同,除非另有说明。例如,可举出二甲基氨基、甲基乙基氨基或甲基-正丙基氨基等。
在本发明中,“(二(C1-C6烷基)亚磺酰亚基)氨基”是指O=S(C1-C6烷基)2=N-基团,其中该二个烷基可彼此不同。例如,可举出(S,S-二甲基亚磺酰亚基)氨基、(S,S-二乙基亚磺酰亚基)氨基、(S-乙基-S-甲基亚磺酰亚基)氨基等。
在本发明中,“二(C1-C6烷基)磷酰基”是指O=P(C1-C6烷基)2基团,其中该二个烷基可彼此不同。例如,可举出二甲基磷酰基、二乙基磷酰基、乙基甲基磷酰基等。
在本发明中,“C1-C7酰基”是指H-C(=O)-基团或(C1-C6烷基)-C(=O)-基团,除非另有说明。例如,可举出甲酰基、乙酰基、丙酰基、异丁酰基或三甲基乙酰基等。
“未经取代或经卤原子取代的C1-C7酰基”在其可取代的位置可具有1至10个,优选为1至5个卤原子。当卤原子的数目为二个或更多个时,该卤原子可相同或不同。
在本发明中,“C1-C7酰氧基”是指(C1-C7酰基)-O-基团,其中该酰基部分具有上述定义,除非另有说明。例如,可举出甲酰氧基、乙酰氧基、丙酰氧基、异丁酰氧基或三甲基乙酰氧基等。
在本发明中,“C1-C7卤代酰基”是指经卤素取代的甲酰基或(C1-C6卤代烷基)-C(=O)-基团,除非另有说明。例如,可举出氯甲酰基、氯乙酰基、三氟乙酰基、三氯乙酰基、2-氯丙酰基、2-氯异丁酰基、2-溴异丁酰基或3-氯三甲基乙酰基等。
在本发明中,“羟基亚氨基(氨基)C1-C6烷基”是指(H2N)C(=NOH)-基团或其中该C1-C6烷基的任何位置被“(H2N)C(=NOH)-“取代的基团。
在本发明中,“羧基”是指HO-C(=O)-基团。
在本发明中,“C1-C6烷氧基羰基”是指(C1-C6烷氧基)-C(=O)-基团。
在本发明中,“N-(C1-C6烷氧基)-N-(C1-C6烷基)氨基羰基”是指(C1-C6烷氧基)(C1-C6烷基)N-C(=O)-基团。
在本发明中,“氨基羰基”是指NH2-C(=O)-基团。
在本发明中,“氨基硫羰基”是指NH2-C(=S)-基团。
在本发明中,“单(C1-C6烷基)氨基羰基”是指(C1-C6烷基)-NH-C(=O)-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、异丙基氨基羰基或叔丁基氨基羰基等。
在本发明中,“单(氰基C3-C6环烷基)氨基羰基”是指(氰基C3-C6环烷基)-NH-C(=O)-基团,其中该氰基C3-C6环烷基部分具有上述定义,除非另有说明。例如,可举出1-氰基环丙基氨基羰基、2-氰基环丙基氨基羰基、1-氰基环丁基氨基羰基、2-氰基环丁基氨基羰基、3-氰基环丁基氨基羰基、1-氰基环戊基氨基羰基、3-氰基环戊基氨基羰基、1-氰基环己基氨基羰基或4-氰基环己基氨基羰基等。
在本发明中,“单(C1-C6烷氧基亚氨基C1-C6烷基)氨基羰基”是指(C1-C6烷氧基亚氨基C1-C6烷基)-NH-C(=O)-基团,其中该C1-C6烷氧基亚氨基C1-C6烷基部分具有上述定义,除非另有说明。例如,可举出甲氧基亚氨基甲基氨基羰基、乙氧基亚氨基甲基氨基羰基等。
在本发明中,“二(C1-C6烷基)氨基亚甲基氨基羰基”是指(C1-C6烷基)2-N-C=N-C(=O)-基团,其中该烷基部分具有上述定义,除非另有说明。例如,可举出二甲基氨基亚甲基氨基羰基、二乙基氨基亚甲基氨基羰基或二异丙基氨基亚甲基氨基羰基等。
在本发明中,“单(C1-C6烷基)氨基硫羰基”是指(C1-C6烷基)-NH-C(=S)-基团,其中该烷基部分具有上述定义,除非另有说明。
在本发明中,“二(C1-C6烷基)氨基羰基”是指(C1-C6烷基)2-N-C(=O)-基团,其中该烷基部分具有上述定义,且该二个烷基可彼此不同,除非另有说明。例如,可举出二甲基氨基羰基、二乙基氨基羰基或二异丙基氨基羰基等。
在本发明中,“二(C1-C6烷基)氨基硫羰基”是指(C1-C6烷基)2-N-C(=S)-基团,其中该烷基部分具有上述定义,且该二个烷基可彼此不同,除非另有说明。
在本发明中,“单(C1-C6卤代烷基)氨基羰基”是指(C1-C6卤代烷基)-NH-C(=O)-基团,其中该卤代烷基部分具有上述定义,除非另有说明。例如,可举出2-氟乙基氨基羰基、2,2-二氟乙基氨基羰基、2,2,2-三氟乙基氨基羰基、2,2,2-三氯乙基氨基羰基或1,1,1,3,3,3-六氟-2-丙基氨基羰基等。
在本发明中,“单(C3-C6环烷基)氨基羰基”是指(C3-C6环烷基)-NH-C(=O)-基团,其中该环烷基部分具有上述定义,除非另有说明。例如,可举出环丙基氨基羰基、环丁基氨基羰基、环戊基氨基羰基、环己基氨基羰基等。
在本发明中,例如“未经取代或任选经R11取代的C6-C12芳基”的标记表示其中结合到碳原子的氢原子被任何R11取代的芳基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当芳基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C5-C12杂芳基”的标记表示其中结合到碳原子的氢原子被任何R11取代的杂芳基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂芳基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C7-C14芳烷基”的标记表示其中结合到碳原子的氢原子被任何R11取代的芳烷基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当芳烷基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C6-C14杂芳烷基”的标记表示其中结合到碳原子的氢原子被任何R11取代的杂芳烷基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂芳烷基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C6-C12芳氧基”的标记表示其中结合到碳原子的氢原子被任何R11取代的芳氧基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当芳氧基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C5-C12杂芳氧基”的标记表示其中结合到碳原子的氢原子被任何R11取代的杂芳氧基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂芳氧基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C7-C14芳烷氧基”的标记表示其中结合到碳原子的氢原子被任何R11取代的芳烷氧基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当芳烷氧基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的C6-C14杂芳烷氧基”的标记表示其中结合到碳原子的氢原子被任何R11取代的杂芳烷氧基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂芳烷氧基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,例如“未经取代或任选经R11取代的杂环基”表示其中结合到碳原子的氢原子被任何R11取代的杂环基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂环基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
在本发明中,杂环基是指具有一个或多个相同或不同的杂原子(例如氮原子、氧原子和/或硫原子)替代一个或多个碳原子的非芳族的单环或多环基团。
在本发明中,杂环基的实例包括,但不限于,具有1至13个碳原子及1至4个独立选自氮、氧和硫原子的杂原子的非芳族的单环、双环或三环及3至14元(优选为4至14元且更佳为5至14元)杂环基。
在本发明中,杂环基的实例包括,具有1至9个碳原子及1至4个独立选自氮、氧和硫原子的杂原子的非芳族的单环、双环及3至10元(优选为4至10元,且更优选为5至10元,最优选为5至7元)杂环基,但不限于此。
进而,在本发明中,杂环基的实例包括,具有1至5个碳原子及1至4个独立选自氮、氧和硫原子的杂原子的非芳族的单环及3至8元(优选为5至6元)杂环基,但不限于此。
单环杂环基的特定实例包括,异噁唑啉基、哌啶基、哌嗪基、氮杂啶基、氮丙啶基、吗啉基、二氢吡喃基、四氢吡喃基、四氢呋喃基、氧杂环丁基、环氧乙烷基、二噁烷基(例如,1,3-二噁烷基、1,4-二噁烷基等)、二环氧乙烷基(例如,1,3-二氧杂环戊烷基等)、噻嗯基(thianyl)、四氢噻吩基、噻坦基(thietanyl)、噻丙环基(thiiranyl)等,但不限于此。
双环杂环基的特定实例包括,吲哚啉基、异吲哚啉基、苯并二氢吡喃基、异苯并二氢吡喃基、四氢异喹啉基、苯并四氢呋喃基、苯并四氢噻吩基、四氢异苯并呋喃基、四氢异苯并噻吩基、苯并二氧戊基、二氢苯并异噁嗪基、二氢苯并异噻嗪基、1-氧代四氢喹啉基、四氢喹啉基、二氢喹啉基、二氢喹啉酮-基、二氢异喹啉酮-基、二氢香豆素基、二氢异香豆素基、异吲哚啉酮-基、苯并二噁烷基、苯并噁唑啉酮-基、喹啶基、吲啶基、莨菪烷基、降莨菪烷基(nortropanyl)、奎宁环基(quinuclidinyl)、3-氮杂双环[3.1.0]己基、6-氧杂-3-氮杂双环[3.1.0]己基等,但不限于此。
对此,取代的位置并没有特别限制。即,杂环基包括所有其位置异构体。例如,当杂环基为哌啶基时,该哌啶基包括1-哌啶基、2-哌啶基、3-哌啶基及4-哌啶基。
如上述定义或示例的杂环基,如果可能,可包括非稠合环状(例如,单环或螺环)及稠合环状基团。
如上述定义或示例的杂环基,如果可能,可以是未饱和、部分饱和或饱和的。
当上述定义或示例的杂环基的杂原子为氮原子时,该氮原子可为N-氧化物。
当上述定义或示例的杂环基的杂原子为硫原子时,该硫原子可为亚磺酰基(-SO-)或磺酰基(-SO2-)。
在本发明中,“杂环基C1-C6烷基”是指其中该C1-C6烷基的任何位置被杂环基取代的基团,其中该杂环基部分及该烷基部分具有上述定义,除非另有说明。例如,可举出(1,3-二噁烷-2-基)甲基等。
在本发明中,例如“未经取代或任选经R11取代的杂环基C1-C6烷基”的标记表示其中结合到碳原子的氢原子被任何R11取代的杂环基C1-C6烷基。被取代的R11的数目任选地在每个指定的碳原子数目的范围选定,例如,1至10个,优选为1至5个。当杂环基C1-C6烷基上有二个或更多个取代基R11时,各个R11可彼此相同或不同。
当羟基、羧基或氨基或吡啶环的氮原子存在于通式[I]表示的本发明化合物的结构中时,本发明中的盐或农业上可接受的盐是由这些基团或原子与金属或有机碱形成的盐,或与无机酸或有机酸形成的盐。该金属的实例包括例如钠和钾的碱金属或例如镁和钙的碱土金属。该有机碱的实例包括三乙胺或二异丙胺等。该无机酸的实例包括磷酸、氢氯酸、氢溴酸、氢碘酸、硼酸或硫酸等。此外,该有机酸的实例包括甲酸、乙酸、乳酸、抗坏血酸、琥珀酸、富马酸、马来酸、草酸、柠檬酸、苯甲酸、水杨酸、酒石酸、甲磺酸、4-甲苯磺酸或三氟甲磺酸等。
随后,将本发明通式[I]表示的杂环化合物中所含的化合物的表示实例显示于表1至表23。然而,包括本发明杂环化合物中的化合物并不限于此。此外,表中的化合物编号将在以下描述。
虽然包括在本发明杂环化合物中的化合物根据取代基的种类可以包括E型和Z型的几何异构体,但E型、Z型、以及E型和Z型的任意比例的混合物均包括在本发明中。此外,虽然包括在本发明中的化合物由于存在一个或多个不对称碳原子和不对称硫原子而可包括光学异构体,但所有光学活性物质、外消旋化合物或非镜像异构体都包括在本发明中。
本文表格中的下列符号分别表示对应的基团,如下所示:
Me:甲基,
Et:乙基,
nPr:正丙基,
iPr:异丙基,
cPr:环丙基,
nBu:正丁基,
sBu:仲丁基,
iBu:异丁基,
tBu:叔丁基,
cBu:环丁基,
nPen:正戊基,
cPen:环戊基,
nHex:正己基,
cHex:环己基,
(1-CN)cPr:1-氰基环丙基,
(2,2-F2)cPr:2,2-二氟环丙基,
Ph:苯基,
(4-CF3)Ph:4-三氟甲基苯基
表1
表2
表3
表4
表5
表6
表7
表8
表9
表10
表11
表12
表13
表14
表15
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表16
表17
表18
表19
表20
表21
表22
表23
表24
化合物编号 | A2 | A3 | A4 | A5 | A6 | R10 |
D-0171 | CH | N | C-CF3 | CH | CH | CH2CF2CHFCF3 |
D-0172 | CH | N | C-cPr | CH | CH | CH2CF2CHFCF3 |
D-0173 | CH | N | C-(2,2-F2)cPr | CH | CH | CH2CF2CHFCF3 |
D-0174 | CH | N | C-(1-CN)cPr | CH | CH | CH2CF2CHFCF3 |
D-0175 | CH | N | C-OCF3 | CH | CH | CH2CF2CHFCF3 |
D-0176 | CH | N | C-OCHF2 | CH | CH | CH2CF2CHFCF3 |
D-0177 | CH | N | C-OC(Me)2CN | CH | CH | CH2CF2CHFCF3 |
D-0178 | CH | N | C-SCF3 | CH | CH | CH2CF2CHFCF3 |
D-0179 | CH | N | C-S(=O)CF3 | CH | CH | CH2CF2CHFCF3 |
D-0180 | CH | N | C-S(=O)2CF3 | CH | CH | CH2CF2CHFCF3 |
制造方法
另一方面,通式[I]表示的本发明化合物可根据以下所述的方法制造,但其制造方法并不限于此。在下文中,例如“由通式[I]表示的化合物”及“由式[I]表示的化合物”和“化合物[I]”为相同的表示方式。
制造方法1
在本发明化合物中,通式[I]表示的化合物根据由以下所述的反应式组成的方法来制造。
(式中,X表示卤原子、或C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、任选经取代的C6-C12芳基磺酰基、C1-C6烷基磺酰氧基、C1-C6卤代烷基磺酰氧基、任选经取代的C6-C12芳基磺酰氧基或C1-C7酰氧基,W1、W2、m、n、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8、A9及R10具有如上述相同的定义。)
即,通式[I]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱的情况下,使通式[II]表示的化合物与通式[III]表示的化合物反应来制造。此外,此反应也可在合适的催化剂存在下进行。
对于1mol化合物[II],此反应中所使用的化合物[III]的量通常在1至100mol的范围适当选择,优选为1至5mol。
当此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾;金属氢化物,例如氢化锂、氢化钠、氢化钾;或有机碱,例如三乙基胺、三丁基胺、N,N-二异丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol的化合物[II],所使用的碱的量可在0至5mol的范围适当选择,优选为0.1至2mol。
可用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[II],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
当反应使用催化剂时,可使用的催化剂包括金属或金属盐及作为配体的化合物。此类催化剂可在反应系统中(原位)由金属或金属盐和作为后述的配体的化合物制造,或者可在反应系统外预先制造,然后再添加到反应系统中。催化剂可包括除金属或金属盐及化合物配体之外的其他成分。金属或金属盐的实例包括铜化合物,例如金属铜、乙酸铜(单价)、乙酸铜(二价)、氧化铜(单价)、氧化铜(二价)、氯化铜(单价)及碘化铜(单价);钯化合物,例如钯碳、氯化钯、硝酸钯、乙酸钯、双(三苯基膦钯二氯化物、四(三苯基膦)钯、三(二亚芐基丙酮)二钯等。配体的实例包括乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-联吡啶、1,10-菲咯啉、新亚铜试剂(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、4,5-双(二苯基膦)-9,9-二甲基黄嘌呤、三苯基膦、1,1'-双(二苯基膦)二茂铁等,及其盐。相对于1mol的金属或金属盐,金属或金属盐与作为配体的化合物的组合可在0.1至10mol的范围适当选择,优选为1至4mol的作为配体的化合物。相对于1mol的化合物[II],所使用的催化剂的量以金属或金属盐计可在0.001至10mol的范围內适当选择,优选为0.01至5mol。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。较好在0℃至180℃的温度范围进行。
虽然此反应的时间是根据反应温度、反应基质、反应量等而变化,但通常为10分钟至48小时。
反应完成后,可通过将反应混合物加入水中并滤出沉淀的固体,或用有机溶剂萃取反应混合物,然后通过浓缩的工序分离化合物[I]。若需要,分离的化合物[I]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法2
在本发明化合物中,通式[I]表示的化合物可根据下述方法制造。
(式中,X、W1、W2、m、n、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8、A9及R10具有如上述相同的定义。)
即,通式[I]表示的化合物可通过在合适的溶剂中,于存在或不存在合适碱的情况下,使通式[IV]表示的化合物与通式[V]表示的化合物反应来制造。此外,此反应也可在合适的催化剂存在下进行。
相对于1mol化合物[IV],此反应中所使用的化合物[V]的量通常在1至100mol的范围适当选择,优选为1至5mol。
当在此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物、例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾;金属氢化物,例如氢化锂、氢化钠、氢化钾;或有机碱,例如三乙基胺、三丁基胺、N,N-二异丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol化合物[IV],所使用的碱的量可在0至5mol的范围适当选择,优选为0.1至2mol。
可用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[IV],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
当在此反应中使用催化剂时,可使用的催化剂包括金属或金属盐及作为配体的化合物。此类催化剂可在反应系统中(原位)由金属或金属盐和作为后述的配体的化合物制造,或者可在反应系统外预先制造,然后再添加到反应系统中。催化剂可包括除金属或金属盐及化合物配体以外的其他成分。金属或金属盐的实例包括铜化合物,例如金属铜、乙酸铜(单价)、乙酸铜(二价)、氧化铜(单价)、氧化铜(二价)、氯化铜(单价)及碘化铜(单价);钯化合物,例如钯碳、氯化钯、硝酸钯、乙酸钯、双(三苯基膦钯二氯化物、四(三苯基膦)钯、三(二亚芐基丙酮)二钯等。配体的实例包括乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-联吡啶、1,10-菲咯啉、新亚铜试剂(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、4,5-双(二苯基膦)-9,9-二甲基黄嘌呤、三苯基膦、1,1'-双(二苯基膦)二茂铁等,及其盐。相对于1mol的金属或金属盐,金属或金属盐与作为配体的化合物的组合可在0.1至10mol的范围适当选择,优选为1至4mol的作为配体的化合物。相对于1mol的化合物[IV],所使用的催化剂的量以金属或金属盐计可在0.001至10mol的范围适当选择,优选为0.01至5mol。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。优选在0℃至180℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至48小时。
反应完成后,可通过将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物,然后通过浓缩的工序分离化合物[I]。若需要,分离的化合物[I]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法3
在本发明化合物中,通式[IX]表示的化合物也可根据下述方法制造。
(式中,R14表示氢原子、卤原子、C1-C6卤代烷基及C1-C6卤代烷氧基,R10’表示在R10中非氢原子的其他取代基,且X、W1、W2、m、n、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8及A9具有如上述相同的定义。)
即,通式[IX]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱的情况下,使通式[VI]表示的化合物与化合物[VII]或化合物[VIII]反应来制造。
相对于1mol化合物[VI],此反应中所使用的化合物[VII]或化合物[VIII]的量通常在1至10mol的范围适当选择,优选为1至2mol。
当在此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾;金属氢化物,例如氢化锂、氢化钠、氢化钾;金属醇盐,例如甲醇钠、乙醇钠、叔丁醇钾;或有机碱,例如三乙胺、三丁胺、N,N-二异丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol化合物[VI],所使用的碱的量可在0至10mol的范围适当选择,优选为0至5mol。
可使用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[VI],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。优选在0℃至100℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至24小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[IX]。若需要,分离的化合物[IX]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法4
在本发明化合物中,通式[I]表示的化合物也可根据下述方法制造。
(式中,X、W1、W2、m、n、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8、A9及R10具有如上述相同的定义。)
即,通式[I]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱的情况下,使通式[X]表示的化合物与通式[XI]表示的化合物反应来制造。此外,此反应也可在合适的催化剂存在下进行。
相对于1mol化合物[X],此反应中所使用的化合物[XI]的量通常在1至5mol的范围适当选择,优选为1至1.5mol。
当在此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾;金属氢化物,例如氢化锂、氢化钠、氢化钾;金属醇盐例如甲醇钠、乙醇钠、叔丁醇钾;或有机碱,例如三乙基胺、三丁基胺、N,N-二异丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol化合物[X],所使用的碱的量可在0至5mol的范围适当选择,优选为0.1至2mol。
用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[X],所使用溶剂的量为0.1至1000公升,优选为0.2至100公升。
当此反应使用催化剂时,可使用的催化剂包括金属或金属盐及作为配体的化合物。此类催化剂可在反应系统中(原位)由金属或金属盐和作为后述的配体的化合物制造,或者可在反应系统外预先制造,然后再添加到反应系统中。催化剂可包括除金属或金属盐及化合物配体以外的其他成分。金属或金属盐的实例包括铜化合物,例如金属铜、乙酸铜(单价)、乙酸铜(二价)、氧化铜(单价)、氧化铜(二价)、氯化铜(单价)及碘化铜(单价);钯化合物,例如钯碳、氯化钯、硝酸钯、乙酸钯、双(三苯基膦钯二氯化物、四(三苯基膦)钯、三(二亚芐基丙酮)二钯等。配体的实例包括乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-联吡啶、1,10-菲咯啉、新亚铜试剂(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、4,5-双(二苯基膦)-9,9-二甲基黄嘌呤、三苯基膦、1,1'-双(二苯基膦)二茂铁等,及其盐。相对于1mol的金属或金属盐,金属或金属盐与作为配体的化合物的组合可在0.1至10mol的范围适当选择,优选为1至4mol的作为配体的化合物。相对于1mol的化合物[X],所使用的催化剂的量以金属或金属盐计可在0.001至10mol的范围适当选择,优选为0.01至5mol。
此反应的反应温度可选自0℃至反应体系回流温度的范围的任意温度。优选在20℃至180℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至24小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[I]。若需要,分离的化合物[I]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法5
在本发明化合物中,通式[XIV]表示的化合物可根据下述方法制造。
(式中,W1、W2、m、n、R1、R2、A1、A2、A3、A4、A5、A6、R8、R9及R10具有如上述相同的定义。)
即,通式[XIV]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱或合适的酸的情况下,使通式[XII]表示的化合物与通式[XIII]表示的化合物反应来制造。
相对于1mol化合物[XII],此反应中所使用的化合物[XIII]的量通常在1至5mol的范围适当选择,优选为1至2mol。
当在此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾;金属氢化物,例如氢化锂、氢化钠、氢化钾;金属醇盐例如甲醇钠、乙醇钠、叔丁醇钾;或有机碱,例如三乙基胺、三丁基胺、N,N-二异丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol化合物[XII],所使用的碱的量可在0至5mol的范围适当选择,优选为0至2mol。
当在此反应中使用酸时,可使用的酸的实例包括无机酸,例如氢氯酸、氢溴酸、硫酸、硝酸和磷酸,以及羧酸,例如乙酸或三氟乙酸。相对于1mol化合物[XII],所使用的酸的量可在0至5mol的范围适当选择,优选为0至2mol。
可使用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[XII],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
此反应的反应温度可选自0℃至反应体系回流温度的范围的任意温度。优选在20℃至100℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至24小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[XIV]。若需要,分离的化合物[XIV]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法6
在本发明化合物中,通式[XVI]表示的化合物可根据下述方法制造。
(式中,m'表示0或1,n”表示1或2,m'和n”的和为1或2,W1、W2、R1、R2、A1、A2、A3、A4、A5、A6,A7、A8、A9及R10具有如上述相同的定义。)
即,通式[XVI]表示的化合物可通过存在或不存在合适催化剂的情况下,在合适的溶剂中,使通式[XV]表示的化合物与合适的氧化剂反应来制造。
可使用于此反应的溶剂的实例包括芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;水或它的混合溶剂。相对于1mol的化合物[XV],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
可用于此反应的氧化剂的实例包括有机过氧化物,例如间氯过氧苯甲酸、过氧甲酸、过氧乙酸或三氟过氧乙酸;无机过氧化物,例如过氧化氢、过锰酸钾、Oxone(注册商标)(E.I.DuPont的商品名,包括过一硫酸氢钾);卤素含氧酸的盐类,例如过碘酸钠或次氯酸钠。相对于1mol化合物[XV],所使用的氧化剂的量可在0.5至5mol的范围,优选为0.9至3mol。
可用于此反应的催化剂的实例包括氯化钌(III)及其水合物、五氧化二钒、偏钒酸钠、钨酸钠等。相对于1mol化合物[XV],所使用的催化剂的量可在0.001至10mol的范围,优选为0.01至1mol。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。优选在-10℃至100℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至24小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[XVI]。若需要,分离的化合物[XVI]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法7
在本发明化合物中,通式[XIX]表示的化合物可根据下述方法制造。
(式中,n'表示0或1,且W1、W2、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8、A9及R10具有如上述相同的定义。)
即,通式[XIX]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱的情况下,使化合物[XVIII]或其盐、化合物[XVII]及合适的氧化剂反应来制造。此外,此反应也可在合适的催化剂存在下进行。
相对于1mol化合物[XVII],此反应中所使用的化合物[XVIII]的量通常在1至100mol的范围适当选择,优选为1至5mol。
可用于此反应的氧化剂的实例包括卤化剂,例如氯、溴、碘、氯胺、N-氯琥珀酰亚胺(NCS)、N-溴琥珀酰亚胺(NBS)、N-碘琥珀酰亚胺(NIS)、1,3-二氯-5,5-二甲基乙内酰脲(DCH)、1,3-二溴-5,5-二甲基乙内酰脲(DBH)、1-溴-3-氯-5,5-二甲基乙内酰脲(BCDMH);及高价碘化合物,例如(二氯碘)苯、(双乙酰氧基碘)苯、(双(三氟乙酰氧基)碘)苯、亚碘酰苯、氧碘基苯、2-氧碘基苯甲酸(IBX)、戴斯-马丁氧化剂(Dess-Martin periodinane,DMP)、2-氧碘基苯磺酸(IBS)。相对于1mol化合物[XVII],所使用的氧化剂的量可在0.5至5mol的范围适当选择,优选为0.9至3mol。
当此反应使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾、氧化镁、氧化铝;金属氢化物,例如氢化锂、氢化钠、氢化钾;金属醇盐,例如甲醇钠、乙醇钠、叔丁醇钾;或有机碱,例如三乙胺、三丁胺、N,N-二异丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol的化合物[XVII],碱的使用量可在0至20mol的范围适当选择,优选为0至10mol。
可使用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[XVII],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
可用于此反应的催化剂的实例包括乙酸铑(II)、三氟乙酸铑(II)、三苯乙酸铑(II)、新戊酸铑(II)、辛酸铑(II)、双[铑(α,α,α',α'-四甲基-1,3-苯二丙酸)],乙酰亚胺酸铑(II)等。相对于1mol化合物[XVII],所使用的催化剂的量可在0.001至10mol的范围适当选择,优选为0.005至1mol。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。优选在0℃至100℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至48小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[XIX]。若需要,分离的化合物[XIX]可通过柱层析、重结晶、蒸馏等进一步纯化。
制造方法8
在本发明化合物中,通式[XXI]表示的化合物可根据下述方法制造。
(式中,W1、W2、R1、R2、A1、A2、A3、A4、A5、A6、A7、A8、A9及R10具有如上述相同的定义。)
即,通式[XXI]表示的化合物可通过在合适的溶剂中,于存在或不存在合适的碱的情况下,使化合物[XVIII]或其盐、化合物[XX]及合适的氧化剂反应来制造。此外,此反应也可在合适的催化剂存在下进行。
相对于1mol化合物[XX],此反应中所使用的化合物[XVIII]的量通常在1至100mol的范围适当选择,优选为1至5mol。
可用于此反应的氧化剂的实例包括卤化剂,例如氯、溴、碘、氯胺、N-氯琥珀酰亚胺(NCS)、N-溴琥珀酰亚胺(NBS)、N-碘琥珀酰亚胺(NIS)、1,3-二氯-5,5-二甲基乙内酰脲(DCH)、1,3-二溴-5,5-二甲基乙内酰脲(DBH)、1-溴-3-氯-5,5-二甲基乙内酰脲(BCDMH);及高价碘化合物,例如(二氯碘)苯、(双乙酰氧基碘)苯、(双(三氟乙酰氧基)碘)苯、亚碘酰苯、氧碘基苯、2-氧碘基苯甲酸(IBX)、戴斯-马丁氧化剂(DMP)、2-氧碘基苯磺酸(IBS)。相对于1mol化合物[XX],所使用的氧化剂的量可在0.5至5mol的范围适当选择,优选为0.9至3mol。
当在此反应中使用碱时,可使用的碱的实例包括碱金属氢氧化物,例如氢氧化锂、氢氧化钠及氢氧化钾;碱土金属氢氧化物,例如氢氧化钙及氢氧化镁;碱金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾及碳酸铯;碱金属碳酸氢盐,例如碳酸氢钠及碳酸氢钾;碱金属氟化物,例如氟化钠及氟化钾;无机碱,例如磷酸三钾、氧化镁、氧化铝;金属氢化物,例如氢化锂、氢化钠、氢化钾;金属醇盐,例如甲醇钠、乙醇钠、叔丁醇钾;或有机碱,例如三乙胺、三丁胺、N,N-二异丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲基吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮杂双环[5.4.0]-7-十一烯。相对于1mol化合物[XX],所使用的碱的量可在0至20mol的范围适当选择,优选为0至10mol。
可使用于此反应的溶剂的实例包括醚类,例如二乙醚、甲基叔丁基醚、环戊基甲基醚、四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、单甘醇二甲醚;芳香烃,例如苯、甲苯、二甲苯、对称三甲苯、氯苯;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷;非质子极性溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲亚砜、环丁砜、1,3-二甲基-2-咪唑啉酮;醇类,例如甲醇、乙醇、2-丙醇、叔丁醇、2-甲氧乙醇;腈类,例如乙腈及丙腈;脂肪烃,例如戊烷、己烷、环己烷及庚烷;吡啶,例如吡啶、甲基吡啶及二甲基吡啶;叔胺,例如三乙胺及三丁胺;水或它的混合溶剂等。相对于1mol的化合物[XX],所使用的溶剂的量为0.1至1000公升,优选为0.2至100公升。
可用于此反应的催化剂的实例包括乙酸铑(II)、三氟乙酸铑(II)、三苯乙酸铑(II)、新戊酸铑(II)、辛酸铑(II)、双[铑(α,α,α',α'-四甲基-1,3-苯二丙酸)]、乙酰亚胺酸铑(II)等。相对于1mol化合物[XX],所使用的催化剂的量可在0.001至10mol的范围适当选择,优选为0.01至5mol。
此反应的反应温度可选自-78℃至反应体系回流温度的范围的任意温度。优选在0℃至100℃的温度范围进行。
虽然此反应的反应时间根据反应温度、反应基质、反应量等而变化,但通常为10分钟至48小时。
反应完成后,可通过例如将反应混合物加入水中并滤出沉淀的固体,或以有机溶剂萃取反应混合物然后浓缩的工序分离化合物[XXI]。若需要,分离的化合物[XXI]可通过柱层析、重结晶、蒸馏等进一步纯化。
通式[II]及[IV]表示的本发明杂环化合物是在制造本发明的通式[I]表示的杂环化合物或其农业上可接受的盐中作为中间体的有用化合物。
本发明的农药组合物含有本发明通式[I]表示的杂环化合物或其农业上可接受的盐作为有效成分。
如果需要,本发明的农药组合物可含有通常用于农药制剂的添加剂成分(载剂)。
本发明的有害生物防治剂含有本发明通式[I]表示的杂环化合物或其农业上可接受的盐作为有效成分。本发明的有害生物防治剂通常是杀昆虫剂、杀螨剂及杀线虫剂。
如果需要,本发明的有害生物防治剂可含有通常用于农药制剂的添加剂成分(载剂)。
添加剂成分的实例包括载剂,例如固体或液体载剂、表面活性剂、粘合剂、胶粘剂、增稠剂、着色剂、扩展剂(拡展剤)、展着剂(展着剤)、抗冻剂、抗结块剂、崩解剂、分解抑制剂等。另外,如果需要,也可使用防腐剂、植物碎片等作为添加剂成分。此外,这些添加剂成分可单独使用,也可两种以上组合使用。
固体载剂的实例包括矿物载剂,例如叶蜡石粘土、高岭土、硅石粘土、滑石、硅藻土、沸石、膨润土、酸性粘土、活性粘土、阿塔帕石粘土(attapargas clay)、蛭石、波来铁(pearlite)、浮石、白碳(合成硅酸、合成硅酸盐等)、二氧化钛;植物载剂,例如木粉、玉米梗、核桃壳、果核、稻壳、锯末、麦麸、大豆粉、粉状纤维素、淀粉、糊精和糖;无机盐载体,例如碳酸钙、硫酸铵、硫酸钠、氯化钾;高分子载剂,例如聚乙烯、聚丙烯、聚氯乙烯、聚乙酸乙烯酯、乙烯-乙酸乙烯酯共聚物、脲醛树脂。
液体载剂的实例包括一元醇,例如甲醇、乙醇、丙醇、2-丙醇、丁醇及环己醇;多元醇,例如乙二醇、二甘醇、丙二醇、己二醇、聚乙二醇、聚丙二醇及甘油;多元醇衍生物,例如丙二醇醚;酮类,例如丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮和异佛酮(isophorone);醚类,例如二乙醚、1,4-二噁烷、溶纤剂(cellosolve)、二丙醚及四氢呋喃;脂肪烃,例如正烷烃、环烷烃、异键烷烃、煤油及矿物油;芳香烃,例如甲苯、C9-C10烷基苯、二甲苯、溶剂油、烷基萘及高沸点芳香烃;卤代烃,例如1,2-二氯乙烷、氯仿及四氯化碳;酯类,例如乙酸乙酯、酞酸二异丙酯、酞酸二丁酯、酞酸二辛酯及己二酸二甲酯;内酯类,例如γ-丁内酯;酰胺类,例如N,N-二甲基甲酰胺、N,N-二乙基甲酰胺、N,N-二甲基乙酰胺及N-甲基-2-吡咯烷酮;腈类,例如乙腈;硫化合物,例如二甲亚砜;植物油,例如大豆油、菜籽油、棉籽油、棕榈油和蓖麻油;及来自植物油的脂肪酸低级烷酯;水等。
表面活性剂的实例包括非离子表面活性剂,例如山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福尔马林冷凝液、聚氧乙烯聚氧丙烯嵌段聚合物、烷基聚氧乙烯聚丙烯嵌段聚合物醚、聚氧乙烯烷基胺、聚氧乙烯脂肪酸酰胺、聚氧乙烯脂肪酸双苯基醚、聚亚烷基苄基苯基醚、聚氧化烯苯乙烯基苯基醚、乙炔二醇、聚氧化烯加成乙炔二醇、聚氧乙烯醚型聚硅氧、酯型聚硅氧、氟表面活性剂、聚氧乙烯蓖麻油及聚氧乙烯氢化蓖麻油;陰离子表面活性剂,例如硫酸烷酯、聚氧乙烯烷基醚硫酸盐、聚氧乙烯烷基苯基醚硫酸盐、聚氧乙烯苯乙烯基苯基醚硫酸盐、烷基苯磺酸盐、金属磺酸盐、磺基琥珀酸烷酯、萘磺酸盐、烷基萘磺酸盐、萘磺酸的福尔马林冷凝液的盐、烷基萘磺酸的福尔马林冷凝液的盐、脂肪酸盐、聚羧酸盐、N-甲基-脂肪酸肌胺酸盐、树脂酸盐、聚氧乙烯烷基醚磷酸盐及聚氧乙烯烷基苯基醚磷酸盐;阳离子表面活性剂,例如月桂基胺盐酸盐、硬脂胺盐酸盐、油胺盐酸盐、硬脂胺乙酸盐、硬脂氨基丙基胺乙酸盐、烷基三甲基铵氯及烷胺盐,例如烷基二甲基苄烷铵氯;两性表面活性剂,例如甜菜碱型,如二烷基二氨基乙基甜菜碱及烷基二甲基芐基甜菜碱,及氨基酸型,如二烷基氨基乙基甘胺酸和烷基二甲基芐基甘胺酸等。
粘合剂及胶粘剂的实例包括羧甲基纤维素及其盐类、糊精、水溶性淀粉、黄原胶、瓜尔胶(guar gum)、蔗糖、聚乙烯吡咯烷酮、阿拉伯胶、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸钠、聚乙二醇、聚环氧乙烷、天然磷脂(例如,头孢酸(cepharic acid)、卵磷脂等)等。
增稠剂的实例包括水溶性聚合物,例如黄原胶、瓜尔胶、羧甲基纤维素、聚乙烯吡咯烷酮、羧乙烯基聚合物、丙烯酸聚合物、淀粉衍生物和多糖;无机细粉,例如高纯膨润土、白炭;有机细粉,例如有机膨润土等。
着色剂的实例包括无机顏料,例如氧化铁、氧化钛、普鲁士兰(prussian blue);有机染料,例如茜素染料、偶氮染料和金属酞菁染料。
扩展剂的实例包括聚硅氧基表面活性剂、纤维素粉末、糊精、修飾淀粉、聚氨基羧酸螯合化合物、交联聚乙烯吡咯烷酮、马来酸/苯乙烯共聚物、甲基丙烯酸共聚物、多元醇聚合物与二羧酸酐的半酯、聚苯乙烯磺酸的水溶性盐、聚氧乙烯键烷二醇、聚氧乙烯炔二醇、炔二醇等。
展着剂的实例包括各种表面活性剂,例如二烷基磺基琥珀酸钠、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯脂肪酸酯;石蜡、萜烯、聚酰胺树脂、聚丙烯酸盐、聚氧乙烯、蜡、聚乙烯烷基醚、烷基酚福尔马林冷凝液、合成树脂乳液等。
抗冻剂的实例包括多元醇类,例如乙二醇、二甘醇、丙二醇和甘油。
抗结块剂的实例包括多糖类,例如淀粉、藻酸、甘露糖和半乳糖;聚乙烯吡咯烷酮、白碳、酯胶、石油树脂等。
崩解剂的实例包括三聚磷酸钠、六偏磷酸钠、金属硬脂酸盐、纤维素粉末、糊精、甲基丙烯酸酯共聚物、聚乙烯吡咯烷酮、聚氨基羧酸螯合化合物、磺化苯乙烯/异丁烯/马来酸酐共聚物、淀粉/聚丙烯腈接枝共聚物等。
分解抑制剂的实例包括干燥剂,例如沸石、生石灰和氧化镁;抗氧化剂,例如酚基、氨基、硫基、磷酸基抗氧化剂;UV吸收剂,例如水杨酸基和二苯基酮基UV吸收剂。
防腐剂的实例包括山梨酸钾、1,2-苯并噻唑-3(2H)-酮等。
植物碎片的实例包括锯末、棕榈、玉米梗、烟梗等。
另一方面,当本发明的有害生物防治剂中含有上述添加剂成分时,对于例如固体载剂或液体载剂的载剂它们的质量含量比例通常选自5%至95%的范围,优选为20至90%,表面活性剂的范围为0.1%至30%,优选为0.5至10%,其他添加剂的范围为0.1至30%,优选为0.5至10%。
使用时,本发明的有害生物防治剂可配制成任何剂型,例如,粉剂、粉末颗粒剂、颗粒剂、可湿性粉剂、水溶性制剂、水分散性颗粒剂、片剂、速溶(jumbo)剂、乳化浓缩剂、油、液体、流动剂(フロアブル剤)、乳剂、微乳剂、悬乳剂、微喷溶液、微胶囊、发烟剂、喷雾剂、饵剂、糊剂等。
在实际使用中,这些制剂可直接使用,或也可在使用前用水稀释至预定浓度。通过常用的施用方法进行本发明化合物的各种制剂或其稀释液的施用,例如喷洒(例如喷洒、雾化、粉化、撒粉、撒粒、水面施用、盒内施用等)、土壤施用(例如混合、灌溉等)、表面施用(例如擦拭、粉末涂覆、覆盖等)、种子处理(例如涂抹、粉末涂覆处理等)、浸泡、毒饵、烟雾施用等。此外,也可将有效成分与草料混合来喂饲牲畜,以防治排泄物中存在的害虫特别是有害昆虫的爆发和生长。
本发明的有害生物防治方法可通过在上述施用方法中使用有效量的本发明通式[I]表示的杂环化合物或其农业上可接受的盐来进行。
本发明的有害生物防治剂中的有效成分的复合比(质量%)是依需要而适当选择,例如在配制成粉末剂、粉末颗粒剂或微粒剂等情况下,在0.01~20%的范围,优选为0.05~10%,在配制成颗粒剂等情况下,在0.1至30%的范围,优选为0.5至20%,在配制成可湿性粉末剂、水分散性颗粒剂等情况下,在1至70%的范围,优选为5至50%,在配制成水溶性制剂、液体等情况下,在1至95%的范围,优选为10至80%,在配制成乳化浓缩剂等情况下,在5至90%的范围,优选为10至80%,在配制成油等情况下,在1至50%的范围,优选为5至30%,在配制成流动剂等情况下,在5至60%的范围,优选为10至50%,在配制成乳剂、微乳剂、悬乳剂等情况下,在5至70%的范围,优选为10至60%,在配制成片剂、饵剂、糊剂等情况下,在1至80%的范围,优选为5至50%,在配制成发烟剂等情况下,在0.1至50%的范围,优选为1至30%,且在配制成喷雾剂等情况下,在0.05至20%的范围,优选为0.1至10%。
将这些制剂稀释至适当浓度并喷洒或直接施用。
当用稀释剂稀释时,本发明的有害生物防治剂通常以0.1至5000ppm的有效成分浓度施用。当以原样使用制剂时,每单位面积的施用量为每公顷0.1至5000g有效成分化合物。然而,并不限于此。
当然,本发明的有害生物防治剂单独使用本发明化合物作为有效成分也足够有效。然而,如果需要,可与其他肥料、农药混合使用,例如杀虫剂、杀螨剂、杀线虫剂、增效剂、杀真菌剂、抗病毒剂、引诱剂、除草剂、植物生长调节剂等,可显示出更佳的效果。
接着,以下举例说明可以混合或组合使用的已知杀虫剂(杀虫活性成分)、杀螨剂(杀螨活性成分)、杀线虫剂(杀线虫活性成分)和增效剂化合物(增效活性成分)。
杀虫活性成分、杀螨活性成分、杀线虫活性成分及增效活性成分:氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、亚灭松(azamethiphos)、阿环那比(acynonapyr)、谷速松·乙基(azinphos-ethyl)、谷速松·甲基(azinphos-methyl)、灭螨醌(acequinocyl)、亚灭培(acetamiprid)、乙酰虫腈(acetoprole)、毆杀松(acephate)、亚环锡(azocyclotin)、阿巴汀(abamectin)、双丙环虫酯(afidopyropen)、阿福拉纳(afoxolaner)、呋虫胺(amidoflumet)、三亚螨(amitraz)、棉铃威(alanycarb)、得灭克(aldicarb)、砜灭威(aldoxycarb)、亚列宁(allethrin)[包括d-顺-反-式和d-反-式]、依杀松(isazophos)、氯唑磷(isamidofos)、水胺硫磷(isocarbophos)、加福松(isoxathion)、抑克斯能(isocycloseram)、甲基亚芬松(isofenphos-methyl)、灭必虱(isoprocarb)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、ε-美氟菊酯(epsilon-momfluorothrin)、伊维菌素(ivermectin)、依米赛松(imicyafos)、益达胺(imidacloprid)、依普宁(imiprothrin)、因达匹(indazapyroxamet)、因得克(indoxacarb)、益化利(esfenvalerate)、爱芬克(ethiofencarb)、爱杀松(ethion)、益斯普(ethiprole)、二溴化乙烯(ethylenedibromide)、依杀螨(etoxazole)、依芬宁(etofenprox)、灭线磷(ethoprophos)、益多松(etrimfos)、依马菌素(emamectin)、因灭汀(emamectin benzoate)、安杀番(endosulfan)、益避宁(empenthrin)、噁唑硫非(oxazosulfyl)、欧杀灭(oxamyl)、灭多松(oxydemeton-methyl)、异亚砜磷(oxydeprofos)、氧乐果(omethoate)、核多角体病病毒(Nuclearpolyhedrosis virus)、硫线磷(cadusafos)、κ-七氟菊酯(kappa-tefluthrin)、κ-毕芬宁(kappa-bifenthrin)、水黄皮素(karanjin)、培丹(cartap)、颗粒病病毒(Granulosisvirus)、加保利(carbaryl)、丁基加保扶(carbosulfan)、加保扶(carbofuran)、γ-BHC(gamma-BHC)、灭杀威(xylylcarb)、拜裕松(quinalphos)、烯虫炔酯(kinoprene)、螨离丹(chinomethionat)、急性麻痺病病毒(Entero virus)、牛壁逃(coumaphos)、冰晶石(cryolite)、可尼丁(clothianidin)、克芬螨(clofentezine)、可芬诺(chromafenozide)、氯虫酰胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、可氯丹(chlordane)、硝基三氯甲烷(chloropicrin)、陶斯松(chlorpyrifos)、陶斯松·甲基(chlorpyrifos-methyl)、克凡派(chlorfenapyr)、克芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氯甲硫磷(chlormephos)、氯普亚列宁(chloroprallethrin)、昆虫痘病毒(Entomopoxi virus)、虹色病毒(Irido virus)、氰虫酰胺(cyazypyr)、氰乃松(cyanophos)、汰芬隆(diafenthiuron)、二胺磷(diamidafos)、赛安勃(cyantraniliprole)、赛派芬(cyetpyrafen)、除螨灵(dienochlor)、唑螨氰(cyenopyrafen)、蔬果磷(dioxabenzofos)、二苯丙醚(diofenolan)、西格玛病毒(Sigma virus)、环溴虫酰胺(cyclaniliprole)、环氧虫啶(cycloxaprid)、双特氯松(dicrotophos)、除线磷(dichlofenthion)、环丁三氟喃(cyclobutrifluram)、乙氰菊酯(cycloprothrin)、二氯松(dichlorvos)、二氯灭嗪(dicloromezotiaz)、大克螨(dicofol)、第昔尼(dicyclanil)、二硫松(disulfoton)、达特南(dinotefuran)、敌螨通(dinobuton)、氯氟氰虫酰胺(cyhalodiamide)、赛洛宁(cyhalothrin)[包括γ体和λ体]、赛芬宁(cyphenothrin)[包括(1R)-反-式]、赛扶宁(cyfluthrin)[包括β型]、二福隆(diflubenzuron)、赛芬螨(cyflumetofen)、氟螨嗪(diflovidazin)、环丙氟虫胺(cyproflanilide)、锡螨丹(cyhexatin)、亚灭宁(cypermethrin)[包括α型、β型、θ型及ζ(zeta)型]、大普达井(dimpropyridaz)、二甲基-2,2,2-三氯-1-羟基乙基膦酸酯(DEP)、甲基毒虫畏(dimethylvinphos)、大灭松(dimethoate)、四氟甲醚菊酯(dimefluthrin)、茉莉酮(jasmone)、顺式-茉莉酮(cis-jasmone)、茉莉酸(jasmonic acid)、茉莉酸甲酯(methyljasmonate)、硅护芬(silafluofen)、灭蝇胺(cyromazine)、虫生线虫(Steinernemacarpocapsae)、昆虫寄生性线虫(Steinernema kushidai)、格拉斯氏线虫(Steinernemaglaseri)、spidoxamat、赐诺特(spinetoram)、赐诺杀(spinosad)、赐派芬(spirodiclofen)、螺虫乙酯(spirotetramat)、赐派酮(spiropidion)、螺甲螨酯(spiromesifen)、苏康脲钠(sulcofuron-sodium)、氟虫胺(sulfluramid)、速杀氟(sulfoxaflor)、治螟磷(sulfotep)、二嗪农(diazinon)、赛果培(thiacloprid)、赛速安(thiamethoxam)、替阿札芬(tioxazafen)、硫敌克(thiodicarb)、硫赐安(thiocyclam)、杀虫双(thiosultap)、治线磷(thionazin)、硫伐隆(thiofanox)、硫灭松(thiometon)、tyclopyrazoflor、四氯虫酰胺(tetrachlorantraniliprole)、乐本松(tetrachlorvinphos)、得脱螨(tetradifon)、氟氰虫酰胺(tetraniliprole)、四氟醚菊酯(tetramethylfluthrin)、治灭宁(tetramethrin)、丁基嘧啶磷(tebupirimfos)、得芬诺(tebufenozide)、得芬瑞(tebufenpyrad)、汰福宁(tefluthrin)、得福隆(teflubenzuron)、内吸磷·S·甲基(demeton-S-methyl)、亚培松(temephos)、第灭宁(deltamethrin)、托福松(terbufos)、泰灭宁(tralomethrin)、拜富宁(transfluthrin)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、棘孢木霉菌(Trichoderma asperellum)、木霉菌(Trichoderma)、拟青霉菌(Paecilomyces)、哈氏木霉菌(Trichoderma harzianum)、三福隆(triflumuron)、三氟杀线酯(trifluenfuronate)、三氟苯嘧啶(triflumezopyrim)、混杀威(trimethacarb)、脱芬瑞(tolfenpyrad)、二溴磷(naled)、尼古丁(nicotine)、nicofluprole、烯啶虫胺(nitenpyram)、奈马克丁(nemadetin)、浓核病毒(Denso virus)、诺伐隆(novaluron)、诺福隆(noviflumuron)、淡紫色拟青霉(Paecilomyces lilacinus)、洋葱假单胞菌(Barkholderia cepacia)、伯克氏菌(Barkholderia rinojensis)、蜡蚧轮枝菌(Verticillium lecanii)、烯虫乙酯(hydroprene)、西泽巴斯德氏菌(Pasteurianishizawae)、穿透巴斯德芽孢菌(Pasteuria penetrans)、液化淀粉芽孢杆菌(Bacillusamyloliquefaciens)、坚强芽孢杆菌(Bacillus firmus)、球形芽孢杆菌(Bacillussphaericus)、枯草杆菌(Bacillus subtillis)、苏云金芽孢杆菌(Bacillusthuringiensis)、苏云金芽孢杆菌(Bacillus thuringiensis)所生产的昆虫毒素、苏云金芽孢杆菌亚种鮎泽(Bacillus thuringiensis subsp.Aizawai)、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis subsp.Israelensis)、苏云金芽孢杆菌库斯克亚种(Bacillus thuringiensis subsp.Kurstaki)、苏云金芽孢杆菌拟步行虫亚种(Bacillusthuringiensis subsp.Tenebrionis)、日本甲虫芽孢杆菌(Bacillus popilliae)、地衣芽孢杆菌(Bacillus licheniformis)、繁米松(vamidothion)、巴拉松(parathion)、甲基对硫磷(parathion-methyl)、合芬宁(halfenprox)、氯虫酰肼(halofenozide)、百亚列宁(bioallethrin)、百亚列宁S-环戊烯基(bioallethrin S-cyclopentenyl)、百列灭宁(bioresmethrin)、双-(2-氯-1-甲基乙基)醚(DCIP)、双三氟虫脲(bistrifluron)、海灭隆(hydramethylnon)、必芬螨(bifenazate)、毕芬宁(bifenthrin)、氟虫双酰胺(pyflubumide)、胡椒基丁醚(piperonyl butoxide)、吡蚜酮(pymetrozine)、白克松(pyraclofos)、吡嗪氟虫腈(pyrafluprole)、必芬松(pyridaphenthion)、毕达本(pyridaben)、三氟甲吡醚(pyridalyl)、百利福腙(pyrifluquinazon)、皮瑞普(pyriprole)、百利普芬(pyriproxyfen)、比加普(pirimicarb)、毕汰芬(pyrimidifen)、嘧螨胺(pyriminostrobin)、亚特松(pirimiphos-methyl)、除虫菊素(pyrethrine)、伐灭磷(famphur)、芬普尼(fipronil)、芬杀螨(fenazaquin)、芬灭松(fenamiphos)、扑灭松(fenitrothion)、芬诺克(fenoxycarb)、苯硫威(fenothiocarb)、酚丁灭宁(phenothrin)[包括(1R)-反-式]、仲丁威(fenobucarb)、芬杀松(fenthion)、赛达松(fenthoate)、芬化利(fenvalerate)、芬普螨(fenpyroximate)、氧化芬佈赐(fenbutatin oxide)、芬普宁(fenpropathrin)、大福松(fonofos)、氟化硫酰(sulfuryl fluoride)、佈嘉信(butocarboxim)、丁酮威(butoxycarboxim)、普亚列宁(prallethrin)、嘧螨酯(fluacrypyrim)、氯氟氰虫酰胺(fluazaindolizine)、氟佐隆(fluazuron)、氟噻虫砜(fluensulfone)、氟吡菌酰胺(fluopyram)、氟乙酸钠盐(sodium fluoroacetate)、氟米塔麦(fluxametamide)、氟环隆(flucycloxuron)、护赛宁(flucythrinate)、氟硫灭(flusulfamide)、赛扶宁(fluthrin)、福化利(fluvalinate)[包括τ(tau)型]、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、氟必灵(flupyrimin)、丁烯氟虫腈(flufiprole)、福芬灵(flufenerim)、氟菌螨酯(flufenoxystrobin)、氟芬隆(flufenoxuron)、氟杀逢(fluhexafon)、氟大灭(flubendiamide)、氟苯氟醚(flupentiofenox)、福灭宁(flumethrin)、氟拉兰(fluralaner)、气铃芬(flurimfen)、普硫松(prothiofos)、氟虫清(protrifenbute)、氟尼胺(flonicamid)、加护松(propaphos)、毆螨多(propargite)、茉莉酸丙酯(prohydrojasmon)、佈飞松(profenofos)、布洛苯胺(broflanilide)、丙氟菊酯(profluthrin)、扑达松(propetamphos)、安丹(propoxur)、福美昆(flometoquin)、新杀螨(bromopropylate)、合赛多(hexythiazox)、六伏隆(hexaflumuron)、细脚拟青霉(Pacilimyces tenuipes)、玫烟色拟青霉菌(Paecilomycesfumosoroceus)、淡紫色拟青霉菌(Paecilomyces lilacinus)、啶菌噁唑(heptafluthrin)、飞达松(heptenophos)、百灭宁(permethrin)、异噻虫唑(benclothiaz)、苯吡莫赛(benzpyrimoxan)、免速达(bensultap)、西脱螨(benzoximate)、免敌克(bendiocarb)、免扶克(benfuracarb)、厚孢普可尼亚菌(Pochonia chlamydosporia)、纤细白僵菌(Beauveriatenella)、巴氏蚕白僵菌(Beauveria bassiana)、布氏白僵菌(Beauveria brongniartii)、巴赛松(phoxim)、裕必松(phosalone)、福赛绝(fosthiazate)、吉福松(fosthietan)、福赐米松(phosphamidon)、益灭松(phosmet)、浏阳霉素(polynactins)、覆灭螨(formetanate)、福瑞松(phorate)、机油(machine oil)、马拉松(malathion)、密灭汀(milbemectin)、灭加松(mecarbam)、甲硫酚磷(mesulfenfos)、灭多威(methomyl)、聚乙醛(metaldehyde)、美氟综(metaflumizone)、达马松(methamidophos)、威百亩(metham)、灭赐克(methiocarb)、灭大松(methidathion)、异硫氰酸甲酯(methyl isothiocyanate)、甲基溴(methylbromide)、氧氯甲氧氯(methoxychlor)、灭芬诺(methoxyfenozide)、甲醚菊酯(methothrin)、美特宁(metofluthrin)、美赐平(methoprene)、治灭虱(metolcarb)、速灭磷(mevinphos)、氯氟醚菊酯(meperfluthrin)、植物单孢菌(Monacrosporiumphymatophagum)、植物单孢菌(Monacrosporium phymatophagum)、亚速灵(monocrotophos)、没氟菊酯(momfluorothrin)、哈氏木霉菌(Trichoderma harzianum)、夜蛾诱剂A(litlure-A)、性诱剂B(litlure-B)、磷化铝(aluminium phosphide)、磷化锌(zincphosphide)、膦(phosphine)、氯芬奴隆(lufenuron)、列卡路(rescalure)、列灭宁(resmethrin)、雷皮菌素(lepimectin)、鱼藤酮(rotenone)、质型多角体病毒(Cytoplasmicpolyhedrosis virus)、芬佈赐(fenbutatin oxide)、氰化钙(calcium cyanide)、有机锡化合物(organotins)、硫酸尼古丁(nicotine-sulfate)、(Z)-11-十四碳烯基乙酸酯、(Z)-11-十六碳烯醛、(Z)-11-十六碳烯=乙酸酯、(Z)-9,12-十四烷二烯=乙酸酯、(Z)-9-十四碳烯-1-醇、(Z,E)-9,11-十四烷二烯=乙酸酯、(Z,E)-9,12-十四烷二烯=乙酸酯、1,1,1-三氯-2,2-双(4-氯苯基)乙烷(DDT)、1,3-二氯丙烯、2,4-二氯-5-{2-[4-(三氟甲基)苯基]乙氧基}苯基2,2,2-三氟乙基亚砜(化学名,CAS注册编号:1472052-11-1)、2,4-二甲基-5-[6-(三氟甲硫基)己基氧基]苯基-2,2,2-三氟乙基亚砜(化学名,CAS注册编号:1472050-34-2)、2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯氧基}-5-(三氟甲基)吡啶(化学名,CAS注册编号:1448758-62-0)、3-氯-2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯氧基}-5-(三氟甲基)吡啶(化学名,CAS注册编号:1448761-28-1)、4,6-二硝基-o-甲酚(DNOC)、4-氟-2-甲基-5-(5,5-二甲基己基氧基]苯基2,2,2-三氟乙基亚砜(化学名,CAS注册编号:1472047-71-4)、Bt蛋白质(Cry1Ab,Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb及Cry34/35Ab1)、甲基丁香油酚、4-(p-乙酰氧基苯基)-2-丁酮、(Z)-10-十四碳烯基=乙酸酯、(E,Z)-4,10-十四烷二烯=乙酸酯、(Z)-8-十二碳烯基=乙酸酯、(Z)-11-十四碳烯基=乙酸酯、(Z)-13-二十碳烯-10-酮、14-甲基-1-十八烯、AKD-1193(编码编号)、BCS-AA10147(编码编号)、CL900167(编码编号)、NA-85(编码编号)、NI-30(编码编号)、O,O-二乙基-O-[4-(二甲基胺磺酰基)苯基]-硫代磷酸酯(DSP)、O-乙基-O-4-(硝基苯基)苯基硫代磷酸酯(EPN)、RU15525(编码编号)、XMC(XMC)、Z-13-二十碳烯-10-酮、ZXI8901(编码编号)及F4260(编码编号)。
接着,以下举例说明可以混合或组合的已知除草剂化合物、除草活性成分或植物生长调节剂的化合物。然而,并不限于此。
除草剂化合物或除草活性成分:
碘苯腈(Ioxynil)(包括锂盐、钠盐、辛酸盐等)、苯草醚(aclonifen)、丙烯醛(acrolein)、草芬定(azafenidin)、亚喜芬(acifluorfen)(包括钠盐等)、四唑嘧磺隆(azimsulfuron)、磺草灵(asulam)、乙草胺(acetochlor)、阿特拉津(atrazine)、莎稗磷(anilofos)、胺唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、杀草强(amitrole)、氯丙嘧啶酸(aminocyclopyrachlor)、氯胺吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、莠灭净(ametryn)、罗摩花叶病毒(Araujia Mosaic Virus)、拉草(alachlor)、损毀链格孢(Alternaria destruens)、亚汰草(alloxydim)(包括钠盐等)、环丙嘧啶醇(ancymidol)、爱速隆(isouron)、依索氯托(isoxachlortole)、抑杀特(isoxaflutole)、异噁草胺(isoxaben)、异癸基醇乙氧基化物(Isodecylalkoholethoxylate)、异丙隆(isoproturon)、卤苯胺唑(ipfencarbazone)、灭草喹(imazaquin)、甲咪唑烟酸(imazapic)(包括与胺的盐等)、依灭草(imazapyr)(包括例如异丙基胺盐等)、咪草酸(imazamethabenz)、甲基咪草酸(imazamethabenz-methyl)、咪草啶酸(imazamox)、乙烟酸(imazethapyr)、依速隆(imazosulfuron)、吲嗪氟胺(indaziflam)、茚草酮(indanofan)、乙基甘草津(eglinazine-ethyl)、戊草丹(esprocarb)、甲基胺苯磺隆(ethametsulfuron-methyl)、抑伏灵(ethalfluralin)、磺噻隆(ethidimuron)、乙氧嘧磺隆(ethoxysulfuron)、氯氟草醚(ethoxyfen)、乙基氯氟草醚(ethoxyfen-ethyl)、乙氧呋草黄(ethofumesate)、乙氧苯草胺(etobenzanid)、epyrifenacil、草藻灭二钠(endothal-disodium)、乐灭草(oxadiazon)、快噁草酮(oxadiargyl)、欧克芬(oxaziclomefone)、环氧嘧磺隆(oxasulfuron)、复祿芬(oxyfluorfen)、欧拉灵(oryzalin)、老布达胡椒病毒(ObudaPepper Virus)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、油酸(oleic acid)、苯酮唑(cafenstrole)、辛酸(caprylic acid)、癸酸(capric acid)、乙基克繁草(carfentrazone-ethyl)、特胺灵(karbutilate)、双酰草胺(carbetamide)、快伏草(quizalofop)、乙基快伏草(quizalofop-ethyl)、乙基快伏草-P(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、野油菜黄单孢菌(Xanthomonas campestris)、莫克草(quinoclamine)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、柠檬酸(citric acid)、草隆(cumyluron)、氯酰草膦(clacyfos)、草甘膦(glyphosate)(包括钠、钾、胺、丙基胺、异丙基胺、铵、异丙基铵、胍、单乙醇胺、胆碱、BAPMA(N,N-双-(氨基丙基)甲基胺)、二甲基胺或三甲基硫盐等盐类)、草铵膦(glufosinate)(包括胺盐或钠盐等)、草铵膦-P(glufosinate-P)、草铵膦-P-钠盐、乙烯草同(clethodim)、炔草酸(clodinafop)、炔丙基炔草酯(clodinafop-propargyl)、二氯吡啶酸(clopyralid)(包括单乙醇胺盐)、异噁草酮(clomazone)、甲氧除草醚(chlomethoxyfen)、氯甲酰草胺(clomeprop)、甲基氯酯磺草(cloransulam-methyl)、豆科畏(chloramben)、氯草敏(chloridazon)、豆磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酞酸二甲酯(chlorthal-dimethyl)、草克乐(chlorthiamid)、氯酰亚胺(chlorphthalim)、甲基整形醇(chlorflurenol-methyl)、克普芬(chlorpropham)、灭落宁(chlorbromuron)、枯草隆(chloroxuron)、氯麦隆(chlorotoluron)、酮螺达(ketospiradox)(包括钠盐、钙盐或铵盐等)、葫芦炭疽刺盘孢菌(Colletotrichum orbiculare)、胶孢炭疽菌(Colletotrichumgloeosporioides)、平头炭疽菌(Colletotrichum truncatum)、紫韧革菌(Chondrostercumpurpureum)、嘧啶肟草醚(saflufenacil)、假蒟亭碱(sarmentine)、氰乙酰腈(cyanazine)、氰胺、氟硫草定(diuron)、乙基乙酰甲草胺(diethatyl-ethyl)、二氧嘧啶三酮(dioxopyritrione)、麦草畏(dicamba)(包括与胺、二乙胺、异丙胺、二甘醇胺、二甲铵、二醇胺、异丙铵、金胺、钾、三乙醇胺(trollamine)、BAPMA(N,N-双-(氨基丙基)甲基胺)、胆碱、钠或锂等的盐类,或酯类,例如甲酯等)、环草敌(cycloate)、环杀草(cycloxydim)、双氯磺草胺(diclosulam)、环丙嘧磺隆(cyclosulfamuron)、环吡宁(cyclopyranil)、环吡瑞莫(cyclopyrimorate)、敌草腈(dichlobenil)、禾草灵(dichlofop)、禾草灵·P·甲基(diclofop-P-methyl)、禾草灵·甲基(diclofop-methyl)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸-P(包括与二甲基铵、钾、钠、胆碱等的盐类,或酯类,例如丁氧乙酯、2-乙基己酯、异辛酯、甲酯等)、敌草快(diquat)、二溴敌草快(diquat dibromide)、氟硫草定(dithiopyr)、环草隆(siduron)、敌乐胺(dinitramine)、乙基环酰草酯(cinidon-ethyl)、西速隆(cinosulfuron)、特乐酚(dinoseb)(包括乙酸盐)、特乐酯(dinoterb)、赛伏草(cyhalofop)、丁基赛伏草(cyhalofop-butyl)、环吡氟草酮(cypyrafluone)、双苯酰草胺(diphenamid)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、西玛津(simazine)、dimesulfazet、二甲草胺(dimethachlor)、戊草津(dimethametryn)、汰草灭(dimethenamid)、汰草灭·P(dimethenamid-P)、西草净(simetryn)、哌草丹(dimepiperate)、恶唑隆(dimefuron)、荧光假单胞菌(Pseudomonasfluorescens)、环庚草醚(cinmethylin)、灭草灵(swep)、磺草酮(sulcotrione)、氟磺唑草胺(sulfentrazone)、草硫膦(sulfosate)、磺酰磺隆(sulfosulfuron)、甲基嘧磺隆(sulfometuron-methyl)、西杀草(sethoxydim)、Scelerothinia minor、特草定(terbacil)、香草隆(daimuron)、疥键霉菌素·A(thaxtomin A)、烟草微绿嵌纹病毒(Tobacco Mild Green Mosaic Tobamovirus)、烟草胞裂病毒(Tobacco Rattle Virus)、茅草枯(dalapon)、噻草啶(thiazopyr)、氟丙嘧草酯(tiafenacil)、唑酮磺吩酸(thiencarbazone)(包括钠盐及甲酯等)、仲草丹(tiocarbazil)、杀丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻吩磺隆(thifensulfuron)、噻黄隆(thifensulfuron-methyl)、甜菜安(desmedipham)、敌草净(desmetryne)、特福披洛米(tetflupyrolimet)、欣克草(thenylchlor)、牧草胺(tebutam)、得匍隆(tebuthiuron)、得杀草(tepraloxydim)、特呋喃三酮(tefuryltrione)、草净津(terbuthylazine)、特丁净(terbutryn)、特丁通(terbumeton)、田宝三酮(tembotrione)、吡草磺(topramezone)、三甲苯草酮(tralkoxydim)、三嗪氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、草达津(trietazine)、三氯比(triclopyr)、丁氧乙基三氯比(triclopyr-butotyl)、三氯比·三乙基铵(triclopyr-triethylammonium)、三氟甲磺隆(tritosulfuron)、三唑磺草酮(tripyrasulfone)、三氟草嗪(trifludimoxazin)、甲基氟胺磺隆(triflusulfuron-methyl)、三福林(trifluralin)、三氟啶磺隆(trifloxysulfuron)(包括钠盐等)、甲基苯磺隆(tribenuron-methyl)、硝黄草酮(tolpyralate)、萘草胺(naptalam)(包括钠盐等)、萘普草(naproanilide)、敌草胺(napropamide)、敌草胺-M(napropamide-M)、烟嘧磺隆(nicosulfuron)、乳酸(lacticacid)、草不龙(neburon)、氟草敏(norflurazon)、伯克氏菌(Burkholderia rinojensis)、万隆(vernolate)、巴拉刈(paraquat)、巴拉刈·二氯化物(paraquat dichloride)、氟氯吡啶酯(halauxifen)、氟氯吡啶酯·苄基(halauxifen-benzyl)、氟氯吡啶酯·甲基(halauxifen-methyl)、伯克氏菌、合氯氟(haloxyfop)、合氯氟·P(haloxyfop-P)、合氯氟·乙氧基乙酯(haloxyfop-etotyl)、合氯氟·P·甲基(haloxyfop-P-methyl)、卤索芬(halosafen)、合速隆(halosulfuron-methyl)、毕克斯隆索(bixlozone)、毕克烂(picloram)(包括与二氯铵、三乙醇胺(trolamine)等的盐类)、氟吡酰草胺(picolinafen)、氟吡草酮(bicyclopyrone)、双草醚·钠(bispyribac-sodium)、唑啉草酯(pinoxaden)、双唑草酮(bipyrazone)、治草醚(bifenox)、哌草磷(piperophos)、双唑草腈(pyraclonil)、磺酰草吡唑(pyrasulfotole)、匹唑芬(pyrazoxyfen)、乙基百速隆(pyrazosulfuron-ethyl)、苄草唑(pyrazolynate)、双丙氨膦(bilanafos)、派芬草(pyraflufen)、吡草醚(pyraflufen-ethyl)、哒草福(pyridafol)、嘧硫草醚·钠(pyrithiobac-sodium)、哒草特(pyridate)、环酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧啶硫蕃(pyrimisulfan)、甲基嘧草醚(pyriminobac-methyl)、派罗克杀草砜(pyroxasulfone)、吡唑磺草胺(pyroxsulam)、棕榈疫霉(Phytophthora palmivora)、棉胺宁(phenisopham)、非草隆(fenuron)、异噁苯砜(fenoxasulfone)、噁唑菌胺(fenoxaprop)(包括甲基、乙基、异丙基酯)、噁唑菌胺·P(fenoxaprop-P)(包括甲酯、乙酯、异丙酯)、芬昆诺三酮(fenquinotrione)、乙基唑禾草酸(fenthiaprop-ethyl)、四唑酰草胺(fentrazamide)、苯唑氟草酮(fenpyrazone)、甜菜宁(phenmedipham)、Phomachenopodicola、茎点霉菌(Phoma herbarum)、巨口茎点霉(Phoma macrostoma)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁酯(butylate)、纵沟柄锈菌(Puccinia canaliculata)、遏兰菜柄锈菌(Puccinia thlaspeos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁苯草酮(butroxydim)、啶嘧磺隆(flazasulfuron)、麦草伏(flamprop)(包括甲酯、乙酯、异丙酯)、麦草伏·M(flamprop-M)(包括甲酯、乙酯、异丙酯)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆(primisulfuron-methyl)、伏寄普丁酯(fluazifop-butyl)、伏寄普·P(fluazifop-P)、伏寄普·P·丁酯、异丙吡草酯(fluazolate)、伏草隆(fluometuron)、乙基乙羧氟草醚(fluoroglycofen-ethyl)、氟酮磺隆·钠盐(flucarbazone-sodium)、氟消草(fluchloralin)、氟吡磺隆(flucetosulfuron)、氟噻甲草酯(fluthiacet-methyl)、氟啶嘧磺隆·甲基(flupyrsulfuron-methyl)(包括钠盐、钙盐或铵盐等)、噻草胺(flufenacet)、氟哒嗪草酯(flufenpyr-ethyl)、四氟丙酸(flupropanate)(包括钠盐)、氟胺草唑(flupoxame)、丙炔氟草胺(flumioxazin)、氟胺草酯(flumiclorac-pentyl)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氯氟吡氧乙酸(fluroxypyr)(包括丁氧基丙酯、异辛酯类,或钠盐、钙盐、铵盐等)、氟咯草酮(flurochloridone)、丙草胺(pretilachlor)、丙苯磺隆(procarbazone)(包括钠盐等)、氨氟乐灵(prodiamine)、三氟丙磺隆(prosulfuron)、苄草丹(prosulfocarb)、喔草酯(propaquizafop)、扑草胺(propachlor)、扑灭津(propazine)、除草灵(propanil)、戊炔草胺(propyzamide)、普乐宝(propisochlor)、咪唑嘧磺隆(propyrisulfuron)、苯胺灵(propham)、氟唑草胺(profluazol)、调环酸钙(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆·钠(propoxycarbazone-sodium)、氯苯噻草酮(profoxydim)、丁溴啶(bromacil)、溴莠敏(brompyrazon)、扑草净(prometryn)、扑灭通(prometon)、溴苯腈(bromoxynil)(包括丁酸、辛酸或庚酸等的酯类)、溴酚肟(bromofenoxim)、溴丁酰草胺(bromobutide)、双氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯·苄基(florpyrauxifen-benzyl)、环嗪酮(hexazinone)、烯草胺(pethoxamid)、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、五氟磺草胺(penoxsulam)、凤果花叶病毒(Pepino Mosaic Virus)、胺苯吡菌酮(heptamaloxyloglucan)、氟丁酰草胺(beflubutamid)、氟丁酰草胺-M(beflubutamid-M)、克草猛(pebulate)、壬酸(pelargonic acid)、酰苯草酮(bencarbazone)、喹草酮(benquitrione)、双苯嘧草酮(benzfendizone)、地散磷(bensulide)、免速隆(bensulfuron)、甲基免速隆、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、本达隆(bentazone)、甲氯酰草胺(pentanochlor)、施得圃(pendimethalin)、本特松(pentoxazone)、氟草胺(benfluralin)、呋草黄(benfuresate)、杀木膦(fosamine)、氟磺胺(fomesafen)、甲酰嘧磺隆(foramsulfuron)、福芬素(forchlorfenuron)、甲氯丙酸(mecoprop)(包括钠、钾、异丙胺、三乙醇胺、二甲胺、二醇胺、三乙醇胺、胆碱等盐类,或乙二酯、2-乙基己酯、异辛酯、甲酯等酯类)、甲氯丙酸·P·钾盐(mecoprop-P-potassium)、磺胺磺隆(mesosulfuron)(包括甲酯等)、硝草酮(mesotrione)、灭草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、苯嗪草酮(metamitron)、甲氯丙酸(metamifop)、威百亩(metam)(包括钠盐等)、甲烷亚砷酸二钠(DSMA)、美西除灵(methiozolin)、甲基香草隆(methyldymuron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲基磺隆(metsulfuron-methyl)、扑多草(metobromuron)、吡喃隆(metobenzuron)、莫多草(metolachlor)、赛克嗪(metribuzin)、甲哌啶氯化物(mepiquatchloride)、灭芬草(mefenacet)、单嘧磺隆(monosulfuron)(包括甲酯、乙酯、异丙酯)、绿谷龙(monolinuron)、草达灭(molinate)、碘甲磺隆(iodosulfuron)、碘甲磺隆甲基钠盐(iodosulfulon-methyl-sodium)、碘芬磺隆(iofensulfuron)、碘芬磺隆·钠盐(iofensulfuron-sodium)、乳氟禾草灵(lactofen)、朗剋三酮(lancotrione)、理有龙(linuron)、rimisoxafen、砜嘧磺隆(rimsulfuron)、环草定(lenacil)、2,2,2-三氯乙酸(TCA)(包括钠盐、钙盐或铵盐等)、2,3,6-三氯苯甲酸(2,3,6-TBA)、2,4,5-三氯苯氧基乙酸(2,4,5-T)、2,4-二氯苯氧基乙酸(2,4-D)(包括胺、二乙胺、三乙醇胺、异丙胺、二甲铵、二醇胺、十二烷基铵、庚基铵、十四烷基铵、三乙基铵、三(2-羟基丙基)铵、三乙醇胺(trollamine)、胆碱、钠或锂等的盐类,或酯类,例如丁氧乙酯、2-丁氧基丙酯、2-乙基己酯、甲酯、乙酯、丁酯、异丁酯、辛酯、戊酯、丙酯、异辛酯、异丙酯、异辛酯、糠基酯等)、2,4-二氯苯氧基丁酸(2,4-DB)(包括胺、二乙胺、三乙醇胺、异丙胺、二甲铵、胆碱、钠或锂等盐类,或酯类,例如异辛酯)、2-氨基-3-氯-1,4-萘醌(ACN)、2-甲基-4-氯苯氧基乙酸(MCPA)(包括钠、二甲基铵、胆碱等盐类,或酯类,例如2-乙基己酯、异辛酯、乙酯等)、2-甲基-4-氯苯氧基丁酸(MCPB)(包括钠盐及乙酯等)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、4,6-二硝基-O-甲酚(DNOC)(包括胺或钠盐等)、(5S)-3-(3,5-二氟苯基)-N-[rel-(3R,5R)-5-(三氟甲基磺酰基氨基甲酰基)四氢呋喃-3-基]-5-乙烯基-4H-异噁唑-5-甲酰胺(化学名,CAS注册编号:2266183-40-6)(国际公开号2018/228986、国际公开号2020/114934)、N4-(2,6-二氟苯基)-6-(1-氟-1-甲基乙基)-1,3,5-三嗪-2,4-二胺(化学名,CAS注册编号:1606999-43-2)(国际公开号2014/064094、国际公开号2015/162164)、(5S)-3-(3,5-二氟苯基)-N-[(3R)-5-(甲基磺酰基氨基甲酰基)-2,3-二氢呋喃-3-基]-5-乙烯基-4H-异噁唑-5-甲酰胺(化学名,CAS注册编号:2266190-06-9)(国际公开号2018/228986、国际公开号2020/114934)、(5R)-3-(3,5-二氟苯基)-5-甲基-N-[rel-(3R,5R)-5-(甲基磺酰基氨基甲酰基)四氢呋喃-3-基]-4H-异噁唑-5-甲酰胺(化学名,CAS注册编号:2266164-36-5)(国际公开号2018/228986、国际公开号2020/114934)、(5R)-3-(3,5-二氟苯基)-N-[(3R)-5-(甲氧基氨基甲酰基)-2,3-二氢呋喃-3-基]-5-甲基-4H-异噁唑-5-甲酰胺(化学名,CAS注册编号:2266170-31-2)(国际公开号2018/228986、国际公开号2020/114934)、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮(化学名,CAS注册编号:2138855-12-4)(国际公开号2017/178582、国际公开号2018/015476)、4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮(化学名,CAS注册编号:1708087-22-2)(国际公开号2015/059262、国际公开号2018/015476)、6-(1-氟环戊基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三嗪-2,4-二胺(化学名,CAS注册编号:1820807-75-7)(国际公开第2015/162164号)、6-(1-氟-1-甲基-乙基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三嗪-2,4-二胺(化学名,CAS注册编号:1606999-21-6)(国际公开号2014/064094、国际公开号2015/162164)、(5S)-3-(3-氟-5-甲基苯基)-N-[rel-(3R,5R)-5-(甲氧基氨基甲酰基)四氢呋喃-3-基]-5-乙烯基-4H-异噁唑-5-甲酰胺(化学名,CAS注册编号:2266292-43-5)(国际公开号2018/228986、国际公开号2020/114934)、6-(1-甲基环丁基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三嗪-4,4-二胺(化学名,CAS注册编号:1607001-97-7)(国际公开号2014/064094、国际公开号2015/162164)、AE-F-150944(编码编号)、F9960(编码编号)、IR-6396(编码编号)、MCPA-硫代乙基、NC-656(编码编号)、SYP-298(编码编号)、SYP-300(编码编号)、S-乙基二丙基硫胺甲酸酯(EPTC)、S-莫多草(S-metolachlor)、S-9750(编码编号)、MSMA(MSMA)及HW-02(编码编号)。
植物生长调节剂:1-萘基乙酰胺、1-甲基环丙烯、1,3-二苯基脲、2,3,5-三碘苯甲酸、2-甲基-4-氯苯氧基丁酸(MCPB)[包括钠盐、乙酯等]、2-(萘-1-基)乙酰胺、2,6-二异丙基萘、3-[(6-氯-4-苯基喹唑啉-2-基)氨基]丙烷-1-醇、4-側氧基-4-(2-苯基乙基)氨基丁酸(化学名,CAS注册编号:1083-55-2)、4-氯苯氧基乙酸(4-CPA)、5-氨基乙酰丙酸盐酸盐、5-(三氟甲基)苯并[b]噻吩-2-羧酸甲酯、AVG(氨基乙氧基乙烯基甘胺酸;aminoethoxyvinylglycine)、正癸醇、安希夫林(anisiflupurin)、四稀雌酮(aviglycine)、环丙嘧啶醇(ancymidol)、离层酸(abscisic acid)、亚赐圃(isoprothiolane)、依纳素(inabenfide)、吲哚乙酸、吲哚丁酸、单克素(uniconazole)、单克素-P、Ecolyst、吲唑酯(ethychlozate)、益收生长素(ethephon)、丙酰艺苔素内酯(epocholeone)、氯化钙、氯化胆碱、羟喹啉硫酸盐(oxine-sulfate)、opabactin、裂殖素(kinetin)、过氧化钙、香旱芹酮(carvone)、喹喔啉(quinabactin)、甲酸钙、坐果酸(cloxyfonac)、坐果酸钾(cloxyfonac-potassium)、果美生长素(cloprop)、克美素(chlormequat)、克美素·氯化物(chlormequat-chloride)、克普芬(chlorpropham)、胆碱、细胞分裂素(cytokinins)、氧化型谷胱甘肽(oxydized glutathione)、氰胺(cyanamide)、氰酸钠、环苯胺(cyclanilide)、2,4-滴丙酸(dichlorprop)(包括二甲基铵、钾、钠及胆碱盐等,或酯类,例如丁氧乙酯、2-乙基己酯、异辛酯、甲酯等)、2,4-滴丙酸-P(包括钠、钾、二甲基铵盐等,或2-乙基己酯等)、敌草快(diquat)、二溴敌草快、环丙酰草胺(dikegulac)、激勃酸(gibberellinic acid)、勃激素A4(gibberellin A4)、勃激素A7、穫萎得(dimethipin)、杀雄啉(sintofen)、茉莉酮(jasmone)、顺式-茉莉酮(cis-jasmone)、茉莉酸(jasmonic acid)、茉莉酸甲酯、键霉素(streptomycin)、石灰硫(calcium polysulfide)、亚拉生长素(daminozide)、碳酸钙、噻苯隆(thidiazuron)、癸烷-1-醇、三十醇(triacontanol)、抑芽唑(triapenthenol)、抗倒酯(trinexapac-ethyl)、脱叶磷(tribufos)、巴克素(paclobutrazol)、石蜡(paraffin)、双草醚·钠盐(bispyribac-sodium)、杀纹宁(hymexazol)、仲丁灵(butralin)、氟噻甲草酯(fluthiacet-methyl)、乙基派芬草(pyraflufen-ethyl)、氟节胺(flumetralin)、调嘧醇(flurprimidol)、芴丁酸(flurenol)、前尼替丁(pronitridine)、茉莉酸丙酯(prohydrojasmon)、调环酸钙(prohexadione-calcium)、胺苯吡菌酮(heptamaloxyloglucan)、6-苄基氨基嘌呤、施得圃(pendimethalin)、福芬素(forchlorfenuron)、刺芒柄花素(formononetin)、马来酸二酰肼(maleic hydrazide)、甲哌啶氯化物(mepiquat chloride)、氟草磺(mefluidide)、脂壳寡糖(lipochitooligosaccharides)(例如脂壳寡糖SP104)、硫化钙。
接着,举例说明可混合或组合使用的用于减少化学损伤的已知化合物。
减少化学损伤的化合物:
双苯噁唑酸(isoxadifen)、双苯噁唑酸·乙基(isoxadifen-ethyl)、解草腈(oxabetrinil)、辛烷-1,8-二胺、解毒喹(cloquintocet)、解草酯(cloquintcet-mexyl)、二狄烈(dietholate)、解草胺腈(cyometrinil)、烯丙酰草胺(dichlormid)、二环酮(dicyclonone)、赛普磺胺(cyprosulfamide)、香草隆(daimuron)、1,8-萘二甲酸酐(1,8-Naphthalic Anhydride)、解草唑(fenchlorazole)、解草唑乙酯(fenchlorazole-O-ethyl)、解草啶(fenclorim)、解草噁唑(furilazole)、氟草肟(fluxofenim)、解草胺(flurazole)、解草嗪(benoxacor)、美卡芬(metcamifen)、米芬能(mephenate)、吡唑二酸(mefenpyr)、吡唑二酸乙基、吡唑二酸-二乙基、低级烷基取代苯甲酸、2,2-二氯-N-(1,3-二氧戊烷-2-基甲基)-N-(2-丙烯基)乙酰胺(PPG-1292)、2-二氯甲基-2-甲基-1,3-二噁烷(MG-191)、3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷(R-29148)、4-二氯乙酰基-1-氧杂-4-氮杂螺环[4.5]癸烷(AD-67)、4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸(CL-304415、编码编号)、MON4660(编码编号)、美卡芬(metcamifen)、N1,N2-二烯丙基-N2-二氯乙酰基甘胺酸酰胺(DKA-24、编码)、1-溴-4-[(氯甲基)磺酰基]苯(CSB)、1-氧杂-4-氮杂螺环[4,5]癸烷-4-二硫代甲酸2-丙烯酯(Carbodithioate)(MG-838、编码编号)、3-(二氯乙酰基)-2,2-二甲基-1,3-噁唑烷(R-28725、编码编号)、R-29148(编码编号)、1-(二氯乙酰基)氮杂烷(TI-35、编码编号)。
接着,以下举例说明可混合或组合使用的杀菌剂(杀菌活性成分)或病害防治剂的化合物。
杀菌活性成分或病害防治剂的化合物:
放射形农杆菌(Agrobacterim radiobacter)、戊环唑(azaconazole)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敌菌灵(anilazine)、安美速(amisulbrom)、氨基吡芬(aminopyrifen)、唑嘧菌胺(ametoctradin)、杀螟丹(aldimorph)、亚汰尼(isotianil)、吡唑萘菌胺(isopyrazam)、异丙噻菌胺(isofetamid)、异氟西波(isoflucypram)、亚赐圃(isoprothiolane)、种菌唑(ipconazole)、艾氟芬喹啉(ipflufenoquin)、抑氟康唑(ipfentrifluconazole)、依普同(iprodione)、抑发利(iprovalicarb)、丙基喜乐松(iprobenfos)、依灭列(imazalil)、双胍辛胺烷苯磺酸盐(iminoctadine-albesilate)、双胍辛胺三乙酸盐(iminoctadine-triacetate)、易胺座(imibenconazole)、应吡福安(inpyrfluxam)、应普马汀A(imprimatin A)、应普马汀B(imprimatin B)、护粒松(edifenphos)、乙环唑(etaconazole)、噻唑菌胺(ethaboxam)、依瑞莫菌胺(ethirimol)、乙氧基喹啉(ethoxyquin)、依得利(etridiazole)、烯赃菌酯(enestroburin)、烯肟菌酯(enoxastrobin)、氟环唑(epoxiconazole)、有机油(organicoils)、噁霜灵(oxadixyl)、噁嗪拉唑(oxazinylazole)、奧赛普林(oxathiapiprolin)、嘉保信(oxycarboxin)、氧喹啉铜(oxine-copper)、氧四环素(oxytetracycline)、噁咪唑反丁烯二酸盐(oxpoconazole-fumarate)、欧索林酸(oxolinic acid)、辛酸铜(copperdioctanoate)、辛噻酮(octhilinone)、甲呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、邻苯基酚(o-phenylphenol)、嘉赐霉素(kasugamycin)、四氯丹(captafol)、加普胺(carpropamid)、多菌灵(carbendazim)、萎锈灵(carboxin)、香旱芹酮(carvone)、假丝酵母(Candida oleophila)、佐氏假丝酵母(Candida saitoana)、快诺芬(quinoxyfen)、昆诺浮美林(quinofumelin)、螨离丹(chinomethionat)、克菌丹(captan)、氟喹唑(quinconazole)、五氯硝基苯(quintozene)、双胍辛盐(guazatine)、硫杂灵(cufraneb)、甲香菌酯(coumethoxystrobin)、丁香菌酯(coumoxystrobin)、键孢粘帚霉菌(Gliocradiumcatenulatum)、白色隐球酵母孢菌(Cryptococcus albidus)、醚菌酯(kresoxim-methyl)、克拉康(clozylacon)、粉红螺旋聚孢霉(Clonostachys rosea)、乙菌利(chlozolinate)、氯吲哚酰肼(chloroinconazide)、四氯异苯(chlorothalonil)、地茂散(chloroneb)、毛壳菌(Chaetomiumcupreum)、微坦盾壳霉(Coniothyrium minitans)、赛座灭(cyazofamid)、乙霉威(diethofencarb)、双氯氰菌胺(diclocymet)、益发灵(dichlofluanid)、二氯苯赛斯(dichlobentiazox)、达灭净(diclomezine)、大克烂(dicloran)、二氯酚(dichlorophen)、腈硫醌(dithianon)、达克利(diniconazole)、达克利·M(diniconazole-M)、锌乃浦(zineb)、敌螨普(dinocap)、大芬灭替(dipymetitrone)、二苯基胺(diphenylamine)、待克利(difenoconazole)、环氟菌胺(cyflufenamid)、二氟林(diflumetorim)、环唑醇(cyproconazole)、赛普洛(cyprodinil)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、二甲基二硫化物(dimethyl disulfide)、烯酰吗啉(dimethomorph)、霜脲氰(cymoxanil)、醚菌胺(dimoxystrobin)、絮绒拟酵母(Pseudozyma flocculosa)、致金黄色假单胞菌(Pseudomonas aureofaciens)、绿针假单胞菌(Pseudomonas chlororaphis)、丁香假单胞菌(Pseudomonas syringae)、荧光假单胞菌(Pseudomonas flurorescens)、罗氏假单胞菌(Pseudomonas rhodesiae)、福美锌(ziram)、硅噻菌胺(silthiofam)、夏南瓜黄斑镶嵌病毒弱毒株(Zucchini yellow mosaic virus)、键霉素(streptomycin)、灰绿链霉菌(Streptomyces griseoviridis)、利迪链霉菌(Streptomyces lygicus)、螺噁茂胺(spiroxamine)、环丙吡菌胺(sedaxane)、辛菌胺(seboctylamine)、苯酰菌胺(zoxamide)、苯并烯氟菌唑(solatenol)、迈隆(dazomet)、大孢兰状菌(Talaromyces flavus)、噻酰菌胺(tiadinil)、腐绝(thiabendazole)、得恩地(thiram)、苯硫脲酯(thiophanate)、甲基硫菌灵(thiophanate-methyl)、赛氟灭(thifluzamide)、得恩地(thiram)、四氯硝基苯(tecnazene)、叶枯酞(tecloftalam)、四氟醚唑(tetraconazole)、咪菌威(debacarb)、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、特比萘芬(terbinafine)、多果定(dodine)、吗菌灵(dodemorph)、三泰隆(triadimenol)、三泰芬(triadimefon)、三挫磷(triazoxide)、水杨菌胺(trichlamide)、三环吡菌威(triclopyricarb)、棘孢木霉菌(Trichoderma asperellum)、深绿木霉(Trichoderma atroviride)、盖氏木霉(Trichoderma gamsii)、子座木霉(Trichoderma stromaticum)、青木霉(Trichodermapaecilomyces)、哈氏拉法木霉(Trichoderma harzianum)、绿木霉(Trichoderma viride)、青绿木霉(Trichoderma virens)、多孢木霉(Trichoderma polysporum)、哈茨木霉(Trichoderma harzianum rifai)、木素木霉(Trichoderma lignorum)、三赛唑(tricyclazole)、灭菌唑(triticonazole)、三得芬(tridemorph)、赛福座(triflumizole)、三氟敏(trifloxystrobin)、嗪胺灵(triforine)、甲苯氟苯胺(tolylfluanid)、脱克松(tolclofos-methyl)、甲磺菌胺(tolnifanide)、托普洛卡(tolprocarb)、代森钠(nabam)、键霉菌素(natamycin)、萘替芬(naftifine)、氯啶(nitrapyrin)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、壬基酚磺酸铜(copper nonyl phenol sulphonate)、多粘类芽孢杆菌(Paenibacillus polymyxa)、洋葱假单胞菌(Barkholderia cepacia)、液化淀粉芽孢杆菌(Bacillus amyloliquefaciens)、简单芽孢杆菌(Bacillus simplex)、枯草芽孢杆菌(Bacillus subtilis)、短小芽胞杆菌(Bacillus pumilus)、地衣芽孢杆菌(Bacillus licheniformis)、免疫球蛋白(harpin protein)、争论贪嗜菌(Variovoraxparadoxus)、维利霉素(validamycin)、氯氟氰菊酯(valifenalate)、成团泛菌(Pantoeaagglomerans)、四唑吡氨酯(picarbutrazox)、联苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、寡雄腐霉(Pythium oligandrum)、氟唑菌酰羟胺(pydiflumetofen)、联苯三唑醇(bitertanol)、乐杀螨(binapacryl)、桧木醇(hinokitiol)、非病原性细菌性软腐病菌(Erwinia carotovora)、非病原性葡萄根瘤菌(Rhizobium vitis)、联苯(biphenyl)、粉病灵(piperalin)、杀纹宁(hymexazol)、唑菌酯(pyraoxystrobin)、百克敏(pyraclostrobin)、联苯吡嗪菌胺(pyraziflumid)、白粉松(pyrazophos)、吡炔虫酰胺(pyrapropoyne)、唑胺菌酯(pyrametostrobin)、甲氧苯啶菌(pyriofenone)、啶菌唑(pyrisoxazole)、必哒克緹(pyridachlometyl)、啶斑肟(pyrifenox)、稗草丹(pyributicarb)、吡菌苯威(pyribencarb)、嘧霉胺(pyrimethanil)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、福美铁(ferbam)、噁唑菌酮(famoxadone)、叶枯净(phenazineoxide)、咪唑菌酮(fenamidone)、烯肟菌胺(fenaminstrobin)、芬瑞莫(fenarimol)、芬诺尼(fenoxanil)、富米綜(ferimzone)、拌种咯(fenpiclonil)、苯吡克咪徳(fenpicoxamid)、胺苯吡菌酮(fenpyrazamine)、芬克座(fenbuconazole)、甲呋酰苯胺(fenfuram)、苯锈啶(fenpropidin)、芬普福(fenpropimorph)、环酰菌胺(fenhexamid)、福尔培(folpet)、苯酞(phthalide)、尖孢镰刀菌(Fusarium oxysporum)、布瑞莫(bupirimate)、麦穗宁(fuberidazole)、保米霉素-S(blasticidin-S)、福拉比(furametpyr)、呋霜灵(furalaxyl)、呋喃羧酸(furancarboxylic acid)、扶吉胺(fluazinam)、氟因菌唑(fluindapyr)、氟嘧菌酯(fluoxastrobin)、氟噁派啉(fluoxapiprolin)、fluoxytioconazole、氟比来(fluopiclide)、氟醚菌酰胺(fluopimomide)、氟吡菌酰胺(fluopyram)、氟酰亚胺(fluoroimide)、氟克杀(fluxapyroxad)、氟喹唑(fluquinconazole)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、护汰宁(fludioxonil)、护硅得(flusilazole)、氟硫灭(flusulfamide)、氟噻唑菌腈(flutianil)、福多宁(flutolanil)、护汰芬(flutriafol)、flufenoxadiazam、氟菌螨酯(flufenoxystrobin)、氟苯醚酰胺(flubeneteram)、flumetylsulforim、氟酰菌胺(flumetover)、氟吗啉(flumorph)、大伏革菌(Phlebiopsis gigantea)、丙氧喹啉(proquinazid)、扑克拉(prochloraz)、扑灭宁(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、溴硝醇(bronopol)、普拔克(propamocarb-hydrochloride)、普克利(propiconazole)、甲基代森锌(propineb)、扑杀热(probenazole)、溴克座(bromuconazole)、福美昆(flometoquin)、吡啶酰菌胺(florylpicoxamid)、菲克利(hexaconazole)、本达乐(benalaxyl)、本达乐·M(benalaxyl-M)、麦锈灵(benodanil)、免赖得(benomyl)、披扶座(pefurazoate)、平克座(penconazole)、宾克隆(pencycuron)、苯并烯氟菌唑(benzovindiflupyr)、佈生(benthiazole)、苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、平氟芬(penflufen)、白克列(boscalid)、福赛得(fosetyl)(包括铝、钙、钠盐等)、保粒霉素(polyoxin)、代森福美锌(polycarbamate)、波尔多液(Bordeaux mixture)、代森锰铜(mancopper)、代森锌锰(mancozeb)、曼普胺(mandipropamide)、杏仁菌酯(mandestrobin)、代森锰(maneb)、遇克尼(myclobutanil)、矿物油、米多霉素(mildiomycin)、灭速克(methasulfocarb)、威百亩(metam)、灭达乐(metalaxyl)、灭达乐·M(metalaxyl-M)、metarylpicoxamid、免得烂(metiram)、美特洛(metyltetraprole)、灭特座(metconazole)、苯氧菌胺(metominostrobin)、灭芬农(metrafenone)、灭派林(mepanipyrim)、甲分三康唑(mefentrifluconazole)、消螨多(meptyldinocap)、灭普宁(mepronil)、碘卡佈(iodocarb)、昆布糖(laminarin)、亚磷酸及盐(phosphorous acid and salts)、碱性氯化铜(copper oxychloride)、银(silver)、乙酸铜(copper(II)acetate)、氧化亚铜(cuprous oxide)、氢氧化铜(copper hydroxide)、碳酸氢钾(potassium bicarbonate)、碳酸氢钠(sodium bicarbonate)、硫(sulfur)、硫酸氧喹啉(oxyquinoline sulfate)、硫酸铜(copper sulfate)、(3,4-二氯异噻唑-5-基)甲基4-(叔丁基)苯甲酸酯(化学名,CAS注册编号:1231214-23-5)、BAF-045(编码编号)、BAG-010(编码编号)、UK-2A(编码编号)、十二烷基苯磺酸双乙烯二胺铜錯盐[II](DBEDC)、MIF-1002(编码编号)、NF-180(编码编号)、乙酸三苯基锡(TPTA)、三苯基氯化锡(TPTC)、氢氧化三苯基锡(TPTH)及F9650(编码编号)。
接着,举例说明可混合或组合使用的生物农药。
生物农药:
菊简管蓟马(Haplothrips brevitubus)、捕食茶黄蓟马(Franklinothripsvespiformis)、豌豆潜蝇姬小蜂(Diglyphus isaea)、丽蚜小蜂(Encarsia formosa)、胡瓜捕植螨(Amblyseius cucumeris)、粉蚧玉棒跳小蜂(Pseudaphycus malinus)、温氏捕植螨(Amblyseius womersleyi)、桃赤蚜蚜茧蜂(Aphidius colemani)、浆角蚜小蜂(Eretmocerus eremicus)、食蚜婴蚊(Aphidoletes aphidimyza)、斯氏钝绥螨(Amblyseiusswirskii)、南方小花蝽(Orius strigicollis)、利小植绥螨(Phytoseiulus persimilis)、退变钝绥螨(Amblyseius degenerans)、利小植绥螨(Phytoseiulus persimilis)、小黑花椿(Orius sauteri)、反颚茧蜂(Dacnusa sibirica)、加州捕植螨(Amblyseiuscalifornicus)、日本通草蛉(Chrysoperla nipponensis)及红蜡蚧扁角跳小蜂(Anicetusbeneficus)。
接着,举例说明可混合或组合使用的农业材料。
农业材料:
乙烯、次氯酸水(限电解于盐酸或氯化钾水溶液得到的)、小苏打、食醋、腐植质、腐植酸、黄腐酸、海藻萃取物、多糖类、氨基酸、微生物材料、来自动植物的功能性成分、微生物代谢物、微生物活化剂、土壤扩展剂、土壤浸透性调节材料、土壤保水材料等,及生物刺激剂。
接着,举例说明可混合或组合使用的农业肥料,肥料包括无机肥料与有机肥料。
农业肥料成分:
氯化铵、硫酸铵、硝酸铵、磷酸二氢铵、硝酸尿素铵、尿素、石灰氮、硝酸钾、过磷酸石灰、重过磷酸石灰、磷酸二氢钾、氯化钾、硫酸钾、碳酸钾、硅酸钾、油粕、鱼粉、米糠、蝙蝠粪肥、发酵鸡粪肥。
以上的本发明的有害生物防治剂可对有害生物呈现优异的防治效果,例如直翅目(Orthoptera)害虫、缨翅目(Thysanoptera)害虫、半翅目(Hemiptera)害虫、鞘翅目(Coleoptera)害虫、双翅目(Diptera)害虫、鳞翅目(Lepidoptera)害虫、膜翅目(Hymenoptera)害虫、粘管目(Collembola)害虫、缨尾目(Thysanura)害虫、蟑螂害虫、拟翅目(Psocoptera)害虫、食毛目(Mallophaga)害虫、叶翅目(Phthiraptera)害虫、植物寄生螨、隐新杆状线虫(Caenorhabditis)、软体动物(mollusca)、其他有害动物、令人不快动物、卫生害虫、寄生虫等。这样的有害生物,可举例说明如以下生物种类。
关于直翅目害虫,可举例说明如黑颈钩额虫(Ruspolia lineosa)、阎魔蟋蟀(Teleogryllus emma)、青松虫(Truljalia hibinonis)、东方蝼蛄(Gryllotalpaorientalis)、小翅稻蝗(Oxya hyla intricate)、殿样飞蝗(Locusta migratoria)、迁徙蝗虫(Melanoplus sanguinipes)、长额负蝗(Melanoplus differentialis)、红脚蝗虫(Melanoplus femurrubrum)、负飞蝗(Atractomorpha lata)、茅蟋蟀(Euscyrtusjaponicus)、日本蚤蝼(Xya japonicus)及其他种类。
关于缨翅目害虫,可举例说明如台湾花蓟马(Frankliniella intonsa)、西方花蓟马(Frankliniella occidentalis)、茶黄蓟马(Scirtothrips dorsalis)、南黄蓟马(Thrips palmi)、葱蓟马(Thrips tabaci)、大豆淡色蓟马(Thrips setosus)、变叶木蓟马(Heliothrips haemorrhoidalis)、稻蓟马(Stenchaetothrips biformis)等,柿田蓟马(Ponticulothrips diospyrosi)、山葵田蓟马(Liothrips wasabiae)、稻田蓟马(Haplothrips aculeatus)及其他种类。
关于半翅目害虫,可举例说明如姬草蝉(Mogannia minuta)、白帶尖胸沫蝉(Aphrophora intermedia)、甘蔗虫(Mahanarva fimbriolata)、西伯利亚脊角蝉(Machaerotypus sibiricus)、盖天姬叶蝉(Arboridia apicalis)、茶绿姬叶蝉(Empoascaonukii)、黑尾叶蝉(Nephotettix cincticeps)、马来黑尾叶蝉(Nephotettix malayanus)、台湾黑尾叶蝉(Nephotettix virescens)、黑条黑尾叶蝉(Nephotettix nigropictus)、电光叶蝉(Recilia dorsalis)、小绿叶蝉(Amrasca biguttula)、檬果褐叶蝉(Idioscopusnitidulus)、檬果绿叶蝉(Idioscopus clypealis)、檬果长突叶蝉(Amritodusatkinsoni)、马铃薯姬叶蝉(Empoasca fabae)、玉米叶蝉(Dalbulus maidis)、菱飞虱子(Pentastiridius apicalis)、班飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvatalugens)、白背飞虱(Sogatella furcifera)、玉米飞虱(Peregrinus maidis)、缟飞虱(Nisia nervosa)、白糖斑点飞虱(Kamendaka saccharivora)、红木耳虫(Achilusflammeus)、蚕甲羽衣(Orosanga japonicus)、褐绿蛾蜡蝉(Mimophantia maritima)、梨木虱(Cacopsylla pyrisuga)、柑桔木虱(Diaphorina citri)、檬果木虱(Calophyamangiferae)、葡萄根瘤蚜(Daktulosphaira vitifoliae)、落叶球蚜虫(Adelgeslaricis)、铁杉球蚜虫(Adelges tsugae)、豌豆长须蚜虫(Acyrthosiphon pisum)、棉蚜虫(Aphis gossypii)、桔卷叶蚜虫(Aphis spiraecola)、萝卜蚜虫(Lipaphis erysimi)、罗卜蚜虫(Brevicoryne brassicae)、桃红蚜虫(Myzus persicae)、麦绿蚜虫(Schizaphisgraminum)、稻麦蚜虫(Rhopalosiphum padi)、小柑桔蚜虫(Toxoptera aurautii)、马铃薯长须蚜虫(Aulacorthum solani)、郁金香长须蚜虫(Macrosiphum euphorbiae)、莴苣蚜虫(Nasonovia ribisnigri)、麦长管蚜虫(Sitobion avenae)、大豆蚜虫(Aphis glycines)、茶刺粉虱(Aleurocanthus camelliae)、柑桔刺粉虱(Aleurocanthus spiniferus)、烟草粉虱(Bemisia tabaci)、银叶粉虱(Bemisia argentifolii)、温室粉虱(Trialeurodesvaporariorum)、草履介壳虫(Drosicha corpulenta)、吹棉介壳虫(Icerya purchasi)、凤梨嫡粉介壳虫(Dysmicoccus brevipes)、柑桔粉介壳虫(Planococcus citri)、桑樹粉介壳虫(Pseudococcus comstocki)、角蜡虫(Ceroplastes ceriferus)、红蜡虫(Ceroplastesrubens)、甘蔗仁介壳虫(Aclerda takahashii)、红园介壳虫(Aonidiella aurantii)、梨圆蚧(Diaspidiotus perniciosus)、桑拟白介壳虫(Pseudaulacaspis pentagoa)、箭头介壳虫(Unaspis yanonensis)、美国牧草盲椿象(Lygus lineolaris)、赤须细绿盲椿象(Trigonotylus caelestialium)、绿盲椿象(Apolygus lucorum)、烟盲蝽(Nesidiocoristenuis)、庭园盲椿象(Halticus bractatus)、杜鹃冠网椿象(Stephanitis pyrioides)、梨冠网椿象(Stephanitis nashi)、菜椿象(Eurydema rugosa)、日本二星椿象(Eysarcorislewisi)、北二星椿象(Eysarcoris aeneus)、稻椿象(Lagynotomus elongatus)、绿稻椿象(Nezara viridula)、小珀椿象(Plautia crossota)、东方稻绿椿象(Nezara antennata)、自然椿象(Eushistus heros)、红带自然椿象(Piezodorus guildini)、水稻自然椿象(Tibraca limbativentris)、绿莓自然椿象(Dichelops furcatus)、台湾园椿象(Mcgacopta cribraria)、梨椿象(Urochela luteovoria)、甘蔗短翅长椿象(Caveleriussaccharivorus)、大目高长椿象(Malcus japonicus)、赤星椿象(Dysdercus cingulatus)、禾蛛缘椿象(Leptocorisa acuta)、中稻缘椿象(Leptocorisa chinensis)、大蛛缘椿象(Anacanthocoris striicornis)、赤姬缘椿象(Rhopalus maculatus)、巴式棕色自然椿象(Scaptocoris castanea)、床虱(Cimex lectularis)及其他种类。
关于鞘翅目害虫,可举例说明如金铜金龟子(Anomara cuprea)、姬金龟子(Anomara rufocuprea)、日本金龟子(Popillia japonica)、小青花金龟子(Oxycetoniajucunda)、樱花金龟子(Anomala geniculata)、犀角金龟子(Oryctes rhinoceros)、茶色长金龟子(Heptophylla picea)、六月金龟子(Phyllophaga cuyabana)、鳶色米象鼻虫(Agriotes ogurae)、金针虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Melanotus okinawensis、褐纹金针虫(Melanotus fortnumi)、小圆花皮蠹(Anthrenusverbasci)、二突翼翅长心蠹虫(Heterobostrychus hamatipennis)、药材死番虫(Stegobium paniceum)、姬蛛甲虫(Pitinus clavipes)、谷盗虫(Tenebroidesmauritanicus)、赤足郭公虫(Necrobia rufipes)、酱曲出尾虫(Carpophilushemipterus)、花粉甲虫(Meligethes aeneus)、背园扁粉虫(Ahasverus advena)、角胸粉扁虫(Cryptolestes ferrugineus)、墨西哥豆甲虫(Epilachna varivestis)、茄二十八星瓢虫(Henosepilachna vigintioctopunctata)、黄粉虫(Tenebrio molitor)、拟谷盗虫(Triboliumcastaneum)、豆芜菁(Epicauta gorhami)、光肩星天牛(Anoplophoraglabripennis)、葡萄虎天牛(Xylotrechus pyrrhoderus)、松斑天牛(Monochamusalternatus)、大豆茎螟虫(Dectes texanus)、绿豆象虫(Callosobruchus chinensis)、科罗拉多金花虫(Leptinotarsa decemlineata)、西部玉米食根虫(Diabrotica virgiferavirgifera)、北部玉米食根虫(Diabrotica barberi)、南部玉米食根虫(Diabroticaundecimpunctata howardi)、瓜叶虫(Aulacophora femoralis)、罗卜叶虫(Phaedonbrassicae)、龟子小叶虫(Cassida nebulosa)、负稻泥虫(Oulema oryzae)、墨西哥豆甲虫(Epilachna varivestis)、黄条叶蚤(Phyllotreta striolata)、茶肖叶甲虫(Demotinafasciculata)、卷心菜跳蚤甲虫(Psylliodes chrysocephala)、大豆叶甲虫(Cerotomatrifurcate)、葡萄削叶甲虫(Colaspis brunnea)、艾俄华削叶甲虫(Colaspiscrinnicornis)、豆潜叶虫(Odontota horni)、甜菜跳甲虫(Chaetocnema pulicaria)、带斑黄瓜叶甲虫(Diabrotica balteata)、甘薯蚁象虫(Cylas formicarius)、苜蓿象鼻虫(Hypera postica)、蔬菜象鼻虫(Listroderes costirostris)、甘薯象鼻虫(Euscepespostfasciatus)、栗果象鼻虫(Curculio sikkimensis)、苜蓿叶象鼻虫(Anthonomusgrandis)、大豆茎象鼻虫(Sternechus subsignatus)、稻象鼻虫(Echinocnemusbipunctatus)、稻水象鼻虫(Lissorhoptrus oryzophilus)、南美稻米水象鼻虫(Oryzophagus oryzae)、玉米象鼻虫(Sitophilus zeamais)、狩猎长喙象鼻虫(Sphenophrus venatus)、甘蔗象鼻虫(Sphenophorus levis)、松木蠹虫(Tomicuspiniperda)、台日截尾长小蠹虫(Crossotarsus niponicus)、褐粉蠹虫(Lyctus brunneus)及其他种类。
关于双翅目害虫,可举例说明如大蚊科的稻大蚊(Tipula aino)、爱虫(Plecianearctica)、蕈蚋(Exechia shiitakevora)、马铃薯黑翅蕈蚊(Pnyxia scabiei)、小黑翅蕈蚊(Bradysia agrestis)、大豆荚瘿蚊(Asphondylia yushimai)、黑森婴蚊(Mayetioladestructor)、黑莓婴蚊(Dasineura oxycoccana)、埃及伊蚊(Aedes aegypti)、淡色库蚊(Culex pipiens pallens)、素木蚋(Simulium takahashii)、稻摇蚊(Chironomusoryzae)、合瘤斑蚊(Chrysops suavis)、牛虻(Tabanus trigonus)、洋葱平顏蚜蝇(Eumerusstrigatus)、柑桔小果蝇(Bactrocera dorsalis)、日本樱桃果蝇(Euphranta japonica)、地中海果蝇(Ceratitis capitata)、非洲菊斑潜蝇(Liriomyza trifolii)、蔬菜斑潜蝇(Liriomyza sativae)、日本稻潜蝇(Agromyza oryzae)、番茄斑潜蝇(Liriomyzabryoniae)、豌豆叶潜蝇(Chromatomyia horticola)、中华葱斑潜蝇(Liriomyzachinensis)、黑腹麦稈潜蝇(Meromyza nigriventris)、斑翅果蝇(Drosophila suzukii)、黄果蝇(Drosophila melanogaster)、大麦水蝇(Hydrellia griseola)、马风蝇(Hippobosca equina)、Parallelpmma sasakawae等,花蝇科的洋葱蝇(Delia antiqua)、欧洲花蝇(Delia platura)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、整蝇(Stomoxys calcitrans)、游荡肉蝇(Sarcophaga peregrina)、马蝇(Gasterophilusintestinalis)、牛蝇(Hypoderma lineatum)、羊狂蝇(Oestrus ovis)及其他种类。
关于鳞翅目害虫,可举例说明如淡缘幅蛾(Endoclita excrescens)、葡萄果蠹蛾(Antispila ampelopsia)、六星黑点豹蠹蛾(Zeuzera leuconotum)、姬木蠹蛾(Cossusinsularis)、乱蚊苹果卷叶蝇(Archips fuscocupreanus)、苹果小褐斑苹果卷叶蛾(Adoxophyes orana fasciata)、小食心虫(Grapholita molesta)、茶卷叶蛾(Homonamagnanima)、大豆食心虫(Leguminivora glycinivorella)、苹果蠹蛾(Cydia pomonella)、欧洲葡萄藤蛾(Lobesia botrana)、葡萄与苹果卷叶蛾(Eupoecilia ambiguella)、黑艳蓑蛾(Bambalina sp.)、茶蓑蛾(Eumeta minuscula)、欧谷蛾(Nemapogon granella)、衣蛾(Tinea translucens)、梨菱巢蛾(Bucculatrix pyrivorella)、桃潜叶蛾(Lyonetiaclerkella)、银纹潜叶蛾(Lyonetia prunifoliella malinella)、茶细蛾(Caloptiliatheivora)、银纹细蛾(Phyllonorycter ringoniella)、柑桔小潜叶蛾(Phyllocnistiscitrella)、葱菜蛾(Acrolepiopsis sapporensis)、小菜蛾(Plutella xylostella)、苹果巢蛾(Yponomeuta orientalis)、苹果小食心蛾(Argyresthia conjugella)、葡萄透翅蛾(Nokona regalis)、小透翅蛾(Synanthedin hector)、马铃薯块茎蛾(Phthorimaeaoperculella)、麦蛾(Sitotroga cerealella)、棉红铃虫(Pectinophora gossypiella)、番茄潜旋蛾(Tuta absoluta)、桃食心蛾(Carposina sasakii)、梨星毛虫(Illiberispruni)、黄刺蛾(Monema flavescens)、稻巢草螟蛾(Ancylolomia japonica)、二化螟蛾(Chilo suppressalis)、瘤野螟蛾(Cnaphalocrocis medinalis)、亚洲玉米螟蛾(Ostriniafurnacalis)、菜心螟蛾(Hellulla undalis)、桃蛀野螟蛾(Conogethes punctiferlis)、瓜绢野螟蛾(Diaphania indica)、禾拟茎草螟蛾(Parapediasia teterrella)、欧洲玉米螟虫(Ostrinia nubilalis)、甘蔗螟虫(Diatraea saccharalis)、粉斑螟蛾(Cadra cautella)、大蜡螟蛾(Galleria mellonella)、葡萄羽蛾(Nippoptilia vitis)、柑桔凤蝶(Papilioxuthus)、菜粉蝶(Pieris rapae)、稻弄蝶(Parnara guttata)、Ascotis selenaria、赤松毛虫(Dendrolimus spectabilis)、带枯叶蛾(Malacosoma neustrium testaceum)、虾壳天蛾(Agrius convolvuli)、茶毒蛾(Arna pseudoconspersa)、姬白纹毒蛾(Orygia recensapproximans)、舞毒蛾(Lymantria dispar)、美国白蛾(Hyphantria cunea)、小地老虎蛾(Agrotis ipsilon)、黄地老虎蛾(Agrotis segetum)、豆银纹夜蛾(Autographanigrisigna)、棉铃实夜蛾(Helicoverpa armigera)、玉米穗虫(Helicoverpa zea)、烟蚜夜虫(Heliothis virescens)、甜菜叶蛾(Spodoptera exigua)、斜纹夜蛾(Spodopteralitura)、黄豆尺夜蛾(Chrysodeixis includens)、草地贪夜蛾(Spodoptera frugiperda)、铜色切夜蛾(Nephelodes minians)及其他种类。
关于膜翅目害虫,可举例说明如玫瑰三节叶蜂(Arge pagana)、栗叶蜂(Apethymuskuri)、红角菜叶蜂(Athalia rosae ruficornis)、板栗婴蜂(Dryocosmus kuriphilus)、黄胡蜂(Vespa simillima xanthoptera)、入侵红火蚁(Solenopsis invicta)、阿根廷蚁(Linepithema humile)、蔷薇切叶蜂(Megachile nipponica)及其他种类。
关于粘管目害虫,可举例说明如黄星园跳蚤(Bourletiella hortensis)及其他种类。
关于缨尾目害虫,可举例说明如西洋蠹鱼(Lepisma saccharina)、敏栉衣鱼(Ctenolepisma villosa)及其他种类。
关于蟑螂害虫,可举例说明如美洲蜚蠊(Periplaneta americana)、德国蜚蠊(Blattella germanica)、台湾白蚁(Odontotermes formosanus)、美国干材白蚁(Incisitermes minor)、截头堆砂白蚁(Cryptotermes domesticus)、家白蚁(Coptotermesformosanus)、日本白蚁(Reticulitermes speratus)及其他种类。
关于拟翅目害虫,可举例说明如粉茶蛀虫(Trogium pulsatorium)、书蠹(Liposcelis corrodens)及其他种类。
关于革翅目害虫,可举例说明如蠼螋(Labodura riparia)及其他种类。
关于食毛目害虫,可举例说明如火鸡翅长园虱(Lipeurus caponis)、牛虱(Damalinia bovis)及其他种类。
关于叶翅目害虫,可举例说明如猪虱(Haematopinus suis)、人虱(Pediculushumanus)、狗虱(Linognathus setosus)、阴虱(Pthirus pubis)及其他种类。
关于螨害虫,可举例说明如麦园红蜘蛛(Penthaleus major)、樱草植食螨(Phytonemus pallidus)、茶细螨(Polyphagotarsonemus latus)、蒲螨(Siteroptessp.)、葡萄短須螨(Brevipalpus lewisi)、孔雀杜克叶螨(Tuckerella pavoniformis)、北始叶螨(Eotetranychus boreus)、柑桔叶螨(Panonychus citri)、苹果叶螨(Panonychus ulmi)、二斑叶螨(Tetranychus urticae)、神泽氏叶螨(Tetranychus kanzawai)、松节螨(Trisetacus pini)、柑桔皮节蜱(Aculops pelekassi)、梨锈蜱(Epitrimerus pyri)、柑桔锈螨(Phyllocoptruta oleivora)、番茄銹螨(Aculops lycopersici)、冬青节螨(Diptacuscrenatae)、橢园斑白螨(Aleuroglyphus ovatus)、腐食酪螨(Tyrophagusputrescentiae)、罗宾根螨(Rhizoglyphus robini)、蜜蜂蟹螨(Varroa jaeobsoni)、鸡皮刺螨(Dermanyssus gallinae)、禽刺螨(Ornithonyssus sylviarum)、微小牛螨(Boophilusmicroplus)、血红扇头螨(Rhipicephalus sanguineus)、长角血螨(Haemaphysalislongicornis)、疥螨(Sarcoptes scabiei)及其他种类。
关于植物寄生隐杆线虫,可举例说明如剑线虫(Xiphinema index)、较小拟毛刺线虫(Paratrichodorus minor)、同杆线虫属(Rhabditella sp.)、野外垫刃属(Aglenchussp.)、头刀线虫属(Cephalenchus sp.)、草莓芽线虫(Nothotylenchus acris)、腐烂茎线虫(Ditylenchus destructor)、肾形线虫(Rotylenchulus reniformis)、双宫螺旋线虫(Helicotylenchus dihystera)、针线虫(Paratylenchus curvitatus)、南方根瘤线虫(Meloidogyne incognita)、北方根瘤线虫(Meloidogyne hapla)、爪哇根瘤线虫(Meloidogyne javanjca)、哥伦比亚根瘤线虫(Meloidogyne chitwoodi)、伪哥伦比亚根瘤线虫(Meloidogyne fallax)、黄金线虫(Globodera rostochiensis)、马铃薯金线虫(Globodera pallida)、大豆萎黄线虫(Heterodera glycines)、甜菜囊肿线虫(HeteroderaSchachtii)、矮化线虫(Tylenchorhynchus claytoni)、螺旋线虫属(Psilenchus sp.)、环纹线虫属(Criconemoides sp.)、柑桔线虫(Tylenchulus semipenetrans)、山茶花丸线虫(Sphaeronema camelliae)、柑桔穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis)、假根瘤线虫(Nacobbus aberrans)、穿刺短体线虫(Pratylenchuspenetrans)、咖啡根腐线虫(Pratylenchus coffeae)、摩洛哥根腐线虫(Pratylenchuszeae)、凤梨根腐线虫(Pratylenchus brachyurus)、平菇根瘤线虫(Iotonchiumungulatum)、燕麦真滑刃线虫(Aphelenchus avenae)、貝西滑刃线虫(Aphelenchoidesbesseyi)、草莓线虫(Aphelenchoides fragariae)、松材线虫(Bursaphelenchusxylophilus)及其他种类。
关于植物寄生软体动物,可举例说明如福寿螺(Pomacea canaliculata)、Leavicaulis alte、非洲大蜗牛(Achatina fulica)、双线蛞蝓(Meghimatiumbilineatum)、琥珀蜗牛(Succinea lauta)、浅园罗盘(Discus pauper)、琥珀蜗牛(Zonitoides yessoensis)、黄蛞蝓(Limax flavus)、亚列蛞蝓(Lehmannia valentiana)、网纹野蛞蝓(Deroceras reticulatum)、黍蜗牛(Parakaliella harimensis)、琉球球蜗牛(Acusta despecta sieboldiana)、扁蜗牛(Bradybaena similaris)及其他种类。
关于其他有害生物,例如有害动物、令人不快动物、卫生害虫、家畜害虫、寄生虫等,可举例说明如克氏原螯虾(Procambarus clarkii)、草鞋虫(Porcellio scaber)、鼠腹(Armadillidium vulgare)、千足(Chilopoda)害虫,例如花蚰蜓(Thereuonematuberculata)及蜈蚣(Scolopendra subspinipes)、双足类(Diplopoda)害虫,例如温室马陆(Oxidus gracilis)、赤背寡妇蜘蛛(Theridiidae hasseltii)、日本红螯蜘蛛(Cheiracanthium japouicum)、黑肥尾蠍(Androctonus crassicauda)、线形动物内部寄生虫,例如人蛔虫(Ascaris lumbricoides)、蛲虫属(Syphacia sp.)及潘氏丝状虫(Wuchereria bancrofti)、扁虫的内部寄生虫,例如双盘吸虫属(Distomum sp.)、肺吸虫(Paragonimus westermanii)、横川吸虫(Metagonimus yokokawai)、日本血吸虫(Schistosoma japonicum)、有钩条虫(Taenia solium)、无钩条虫(Taeniarhynchussaginatus)、包囊虫(Echinococcussp.)、广节裂头条虫(Diphyllobothrium latum)及其他种类。
本发明的有害生物防治剂对于现存有害生物防治剂已得到抗性的上述列举的有害生物等也呈现防治效果。此外,本发明的有害生物防治剂也可用于通过基因重组、人工交配等得到抗害虫、抗病、抗除草剂等特性的植物。
本发明的“通过育种方法或基因重组技术已被赋予抗性的植物”不仅包括以标准品种育种及基因重组技术赋予抗性,也包括那些通过将分子生物学技术与传统育种技术相结合的新植物育种技术(NBT)产生抗性的植物。新植物育种技术(NBT)记载于书籍“Let'sUnderstand New Plant Breeding Technology”(International Literature Company,Ryo Osawa and Hiroshi Egami),综述“Genome Editing Tools in Plants”(Genes 2017,8,399,Tapan Kumar Mohanta,Tufail Bashir,Abeer Hashem,Elsayed Fathi Abd_Allah,and Hanhong Bae)等。
实施例
接下来,用下述的实施例详细说明本发明化合物的制造方法、制剂方法及其用途。然而,本发明不受这些实施例限制。关于本发明化合物的物理性质,熔点以Yanaco MP-500V微熔点仪测量,使用Atago制造的Abbe折射仪测量折射率,且以通过使用四甲基硅烷(TMS)作为内标的JEOL所制造的JNM-ECS300(300MHz)量测1H-NMR光谱。
此外,也公开了用于制造本发明化合物中间体的方法。
实施例1
制造1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本发明化合物编号:A-0479)
1)2-[4-(芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶
将根据国际公开号2019/124548合成的2-溴-6-(三氟甲基)咪唑并[1,2-a]吡啶(1.0g,3.8mmol)、4-(芐氧基)-1H-吡唑(0.66g,3.8mmol)、碘化亚铜(I)(0.36g,1.9mmol)、N,N'-二甲基乙二胺(0.17g,1.9mmol)及磷酸三钾n水合物(1.6g,7.5mmol作为无水物)按顺序添加到N-甲基-2-吡咯烷酮(7.5mL),并在密封管中于140℃进一步搅拌8小时。将反应溶液倒入稀释氨水中。添加乙酸乙酯,并将混合物通过硅藻土过滤。有机层用水和饱和盐水洗涤。有机层经过无水硫酸镁干燥,并在减压下蒸馏除去溶剂。残余物通过硅胶柱层析纯化,并得到2-[4-(芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.40g,产率:30%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):5.03(2H,s),7.31-7.46(6H,m),7.53(1H,s),7.64(1H,d),7.88(1H,s),8.02(1H,s),8.49(1H,br s)
2)2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶
将2-[4-(芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.40g,1.1mmol)溶于乙腈(11mL)。将N-碘琥珀酰亚胺(0.30g,1.3mmol)加入混合物,并在室温下进一步搅拌过夜。将反应溶液倒入硫代硫酸钠水溶液中并用乙酸乙酯萃取。有机层依次以碳酸钾水溶液和硫代硫酸钠水溶液洗涤,并将有机层用无水硫酸镁干燥。在减压下蒸馏除去溶剂,并得到2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.46g,产率:85%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):5.04(2H,s),7.32-7.48(6H,m),7.63(1H,d),7.64(1H,d),8.03(1H,d),8.62-8.63(1H,m)
3)1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本发明化合物编号:A-0479)
将2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.46g,0.95mmol)、乙硫醇(0.69mL,9.6mmol)、N,N-二异丙基乙基胺(0.15g,1.2mmol)、三(二亚芐基丙酮)二钯(0)(0.043g,0.047mmol)及Xantphos(0.055g,0.095mmol)按顺序添加到1,4-二噁烷(9.5mL),并将混合物在加热回流下进一步搅拌3小时。浓缩反应溶液。残余物通过硅胶柱层析纯化,并得到2-[4-(芐氧基)-1H-吡唑-1-基]-3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶。将所得到的2-[4-(芐氧基)-1H-吡唑-1-基]-3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶溶于硝基甲烷(9.5mL)。将氯化铝(0.29g,2.2mmol)加入混合物,并在室温下进一步搅拌1小时。将反应溶液倒入稀盐酸并用乙酸乙酯萃取。有机层经过无水硫酸镁干燥,并在减压下蒸馏除去溶剂。将残余物用己烷/二异丙基醚(1:1)混合溶液洗涤,并得到1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(0.27g,产率:86%)。
1H-NMR数据(300MHz,DMSO-d6/TMSδ(ppm)):1.06(3H,t),2.91(2H,q),7.52(1H,d),7.71(1H,dd),7.85(1H,d),7.90(1H,d),8.97(1H,br s),9.08(1H,s)
熔点:199-202℃
实施例2
制造3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶(本发明化合物编号:A-0046)
将1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(0.27g,0.82mmol)、碳酸钾(0.17g,1.2mmol)及2,2,3,3,4,4,4-七氟丁基九氟丁磺酸酯(0.44g,0.91mmol)按顺序添加到N,N-二甲基甲酰胺(8.2mL),并将混合物在室温进一步搅拌过夜。将反应溶液倒入水中并用乙酸乙酯萃取。有机层用水和饱和盐水洗涤,并将有机层经由无水硫酸镁干燥。在减压下蒸馏去除溶剂,得到3-(乙基硫基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶。将所得到的3-(乙基硫基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶溶于二氯甲烷(7.3mL)。将间氯过氧苯甲酸(含量:77%,0.35g,1.6mmol)加入混合物,并在室温下进一步搅拌3小时。将反应溶液倒入碳酸钾水溶液中并用乙酸乙酯萃取。有机层经过无水硫酸镁干燥,并在减压下蒸馏除去溶剂。残余物通过硅胶柱层析纯化,并得到3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.26g,产率:66%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):1.42(3H,t),3.91(2H,q),4.44(2H,tt),7.66(1H,dd),7.67(1H,d),7.77(1H,d),8.06(1H,d),9.63-9.65(1H,m)
熔点:134-136℃
实施例3
制造2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(本发明化合物编号:A-0612)
1)6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a]吡啶
将根据国际公开号2009/144395说明书合成的6-溴-2-氯咪唑并[1,2-a]吡啶(3.50g,15mmol)、二乙基二硫醚(2.77g,23mmol)及碘苯二乙酸酯(7.31g,23mmol)按顺序添加到乙腈(30mL),并将混合物在加热下进一步搅拌,并回流4小时。将反应溶液倒入硫代硫酸钠水溶液中并用乙酸乙酯萃取。有机层用水和饱和盐水洗涤。有机层经过无水硫酸镁干燥,并在减压下蒸馏除去溶剂。残余物通过硅胶柱层析纯化。得到6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a]吡啶(3.81g,产率:86%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):1.23(3H,t),2.75(2H,q),7.37(1H,dd),7.47(1H,dd),8.51(1H,d)
2)6-溴-2-氯-3-(乙基磺酰基)咪唑并[1,2-a]吡啶
将6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a]吡啶(3.81g,13mmol)溶于氯仿(65mL)。在冰冷却下将间氯过氧苯甲酸(含量:70%,8.05g,33mmol)添加到混合物中,并进一步在室温搅拌3小时。将反应溶液倒入碳酸钾水溶液中。加入硫代硫酸钠水溶液,并以氯仿萃取。有机层以碳酸钾水溶液和饱和盐水洗涤,并用无水硫酸镁干燥。在减压下馏出溶剂。得到6-溴-2-氯-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(4.20g,产率:99%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):1.36(3H,t),3.37(2H,q),7.58(2H,m),9.16(1H,d)
3)2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(本发明化合物编号:A-0612)
将6-溴-2-氯-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(4.13g,13mmol)、4-(芐氧基)-1H-吡唑(2.45g,14mmol)及碳酸铯(6.24g,19mmol)按顺序添加到二甲亚砜(26mL)中,并在100℃进一步搅拌8小时。将反应溶液倒入水中并以乙酸乙酯萃取。有机层以饱和盐水洗涤,经由无水硫酸镁干燥,并在减压下蒸馏除去溶剂。残余物以丙酮/二异丙醚(1:1)的混合溶剂洗涤。得到2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(2.68g,产率:46%)。
1H-NMR数据(300MHz,DMSO-d6/TMSδ(ppm)):1.30(3H,t),3.90(2H,q),5.09(2H,s),7.32-7.49(5H,m),7.78-7.87(3H,m),8.16(1H,d),9.17(1H,d)
实施例4
制造1-[6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本发明化合物编号:A-0476)
将2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶(2.68g,5.8mmol)溶于硝基甲烷(29mL)及二氯甲烷(29mL)中。将氯化铝(1.55g,12mmol)添加到混合物中,并在室温进一步搅拌1小时。将稀盐酸倒入反应溶液中,并加入二异丙醚以沉淀粗晶体。以二异丙醚洗涤粗晶体。得到1-[6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(1.72g,产率:80%)。
1H-NMR数据(300MHz,DMSO-d6/TMSδ(ppm)):1.29(3H,t),3.90(2H,q),7.54(1H,d),7.77-7.85(3H,m),9.17(1H,d),9.17(1H,br s)
实施例5
制造6-溴-3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]咪唑并[1,2-a]吡啶(本发明化合物编号:A-0039)
将1-[6-溴-3-(乙基磺酰基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(1.58g,4.3mmol)、碳酸钾(0.88g,6.4mmol)及2,2,3,3,4,4,4-七氟丁基九氟丁磺酸酯(2.26g,4.7mmol)按顺序添加到乙腈(21mL),并进一步在80℃搅拌4小时。浓缩反应溶液,并将残余物通过硅胶柱层析纯化。得到6-溴-3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]咪唑并[1,2-a]吡啶(2.13g,产率:90%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):1.40(3H,t),3.87(2H,q),4.43(2H,tt),7.53-7.65(3H,m),8.01(1H,d),9.38(1H,d)
熔点:171-174℃
实施例6
制造6-环丙基-3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]咪唑并[1,2-a]吡啶(本发明化合物编号:A-0049)
将6-溴-3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]咪唑并[1,2-a]吡啶(4.25g,7.7mmol)、环丙基硼酸(1.32g,15mmol)、磷酸三钾n水合物(4.89g,23mmol作为无水物)、乙酸钯(II)(0.086g,0.38mmol)及2-二环己基膦-2',6'-二甲氧基联苯(0.32g,0.78mmol)按顺序加入1,4-二噁烷(40mL)及水(4mL)中,在加热下进一步搅拌并回流6小时。将反应溶液倒入水中并用乙酸乙酯萃取。有机层用水及饱和盐水洗涤,经过无水硫酸镁干燥,并在减压下蒸馏除去溶剂。残余物通过硅胶柱层析纯化。得到6-环丙基-3-(乙基磺酰基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]咪唑并[1,2-a]吡啶(2.02g,产率:52%)。
1H-NMR数据(300MHz,CDCl3/TMSδ(ppm)):0.76(2H,m),1.06(2H,m),1.39(3H,t),1.99(1H,m),3.81(2H,q),4.42(2H,tt),7.21(1H,dd),7.55(1H,dd),7.62(1H,d),7.98(1H,d),9.01(1H,d)
熔点:117-120℃
根据上述实施例合成的本发明化合物[I]的物理性质值显示于下表25至30中,包括上述实施例中的值。表中的化合物编号和符号具有如上述相同的定义。
表25
表26
表27
表28
表29
表30
接下来,将具体说明如上述制造的杂环化合物或其农业上可接受的盐的本发明有害生物防治剂的制剂实施例。然而,化合物和添加剂的类型和混合比例并不限于此,并可在很宽的范围变化。此外,在以下说明中,“份”是指质量份。
将上述成分均匀溶解可得到乳剂。
将上述成分混合均匀并粉碎可得到可湿性粉剂。
将上述成分混合均匀并粉碎可得到粉剂。
将上述成分混合均匀并粉碎。将相当于20份的数量的水加入混合物中,捏合,使用挤压造粒机加工成14至32网目的颗粒,然后干燥可得到颗粒剂。
将上述成分以高速搅拌器混合30分钟,然后以湿式粉碎机粉碎可得到悬浮浓缩物。
将上述成分混合、捏合、压制和造粒。将得到的颗粒在流体化床干燥器中干燥可得到水分散性颗粒。
接下来,参照测试实施例说明本发明的有害生物防治剂的效果。
[测试实施例1]对于小菜蛾(Plutella xylostella)的杀虫活性测试
将根据制剂实施例2制造的可湿性粉剂用水稀释至500ppm的浓度来作为有效成分。将一些高丽菜叶浸入药物溶液中,风干,然后放入塑料杯中。将10支小菜蛾二齡幼虫放在处理过的叶子上,并盖上盖子。然后,将其放置在恒温25℃的房间中。在处理后6天调查死亡昆虫的数量。使用式1计算死亡率。在每个测试中重复的数量是一次。
[式1]
以下列出在测试中显示出90%或更高死亡率的化合物编号。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0042、A-0044、A-0045、A-0046、A-0047、A-0049、A-0050、A-0056、A-0058、A-0060、A-0068、A-0075、A-0162、A-0164、A-0183、A-0184、A-0185、A-0189、A-0191、A-0192、A-0193、A-0195、A-0199、A-0207、A-0209、A-0210、A-0213、A-0218、A-0256、A-0259、A-0274、A-0423、A-0426、A-0458、A-0579、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0587、A-0589、A-0590、A-0591、A-0592、A-0593、A-0594、A-0595、A-0596、A-0597、A-0598、A-0599、A-0600、A-0602、A-0603、A-0604、A-0605、A-0606、A-0607、A-0608、A-0610、A-0611、A-0613、A-0614、A-0615、B-0002、C-0030、D-0006和D-0021。
[测试实施例2]对于棉铃实夜蛾(Helicoverpa armigera)的杀虫活性测试
将根据制剂实施例2制造的可湿性粉剂用水稀释至500ppm的浓度来作为有效成分。将一些高丽菜叶浸入药物溶液中,风干,然后放入塑料杯中。将5支棉铃实夜蛾孵化幼虫放在处理过的叶子上,并盖上盖子。然后,将其放置在恒温25℃的房间中。在处理后6天调查死亡昆虫的数量。使用式1计算死亡率。在每个测试中重复的数量是二次。
以下列出测试中显示出90%或更高死亡率的化合物编号。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0044、A-0046、A-0049、A-0058、A-0183、A-0207、A-0209、A-0210、A-0213、A-0218、A-0259、A-0274、A-0423、A-0426、A-0458、A-0583、A-0584、A-0587、A-0589、A-0591、D-0006和D-0021。
[测试实施例3]对于褐飞虱(Nilaparvata lugens)的杀虫活性测试
将制剂实施例2制造的可湿性粉剂用水稀释至500ppm的浓度来作为有效成分。将一些稻米芽浸入药物溶液中并放入塑料杯中。将10支褐飞虱二齡幼虫放在处理过的叶子上,并盖上盖子。然后,将其置于25℃的恒定室温中。在处理后6天调查死亡昆虫的数量。使用式1计算死亡率。在每个测试中重复的数量是一次。
以下列出在测试中显示出90%或更高死亡率的化合物编号。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0044、A-0045、A-0046、A-0049、A-0050、A-0056、A-0058、A-0162、A-0164、A-0183、A-0184、A-0210、A-0213、A-0218、A-0579、A-0580、A-0584、A-0592、A-0593、A-0594、A-0595、A-0600、A-0605、A-0611、A-0613、A-0614和C-0026。
[测试实施例4]对于棉蚜虫(Aphis gossypii)的防治效果测试
将制剂实施例2制造的可湿性粉剂用水稀释至500ppm的浓度来作为有效成分。将一些先前接种有棉蚜幼虫的黄瓜苗圃浸入药物溶液中并风干。将处理过的黄瓜苗圃置于25℃恒温的室内。在处理后3天计数存活昆虫的数量。使用式1计算死亡率。在每个测试中重复的数量是一次。
以下列出在测试中显示出90%或更高死亡率的化合物编号。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0042、A-0044、A-0045、A-0046、A-0047、A-0049、A-0050、A-0056、A-0058、A-0162、A-0164、A-0183、A-0184、A-0185、A-0189、A-0191、A-0195、A-0199、A-0207、A-0210、A-0213、A-0218、A-0259、A-0274、A-0423、A-0426、A-0579、A-0580、A-0581、A-0582、A-0584、A-0585、A-0589、A-0590、A-0591、A-0592、A-0593、A-0594、A-0595、A-0596、A-0597、A-0598、A-0599、A-0600、A-0603、A-0604、A-0605、A-0607、A-0608、A-0610、A-0611、A-0614、C-0026、D-0006和D-0021。
产业可利用性
本发明提供具有优异杀虫活性的新的化合物、它的生产中间体以及含有该化合物作为有效成分的有害生物防治剂。其可用于农药和农业领域,并具有工业用途的潜力。
Claims (26)
1.一种通式[I]表示的化合物或其盐,
式中,m及n各自独立地表示0、1或2的整数,且其总和为0至2的整数,
R1表示氢原子、氰基或未经取代或经卤原子取代的C1-C7酰基,
R2表示C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、氰基C1-C6烷基、氰基C3-C6环烷基、未经取代或任选经R11取代的C7-C14芳烷基、或未经取代或任选经R11取代的C6-C14杂芳烷基,
W1表示氮原子,
W2表示碳原子,或
W1表示碳原子,
W2表示氮原子,
A1表示氮原子、经Ra取代的碳原子、或键,
A2表示氮原子、经Rb取代的碳原子、或键,
A3表示氮原子、经R3取代的碳原子、或键,
A4、A5、A6、A7、A8及A9各自独立地表示氮原子、或分别经R4、R5、R6、R7、R8及R9取代的碳原子,
Ra、Rb、R3、R4、R5、R6、R7、R8及R9各自独立地表示氢原子、卤原子、叠氮基、氰基、硝基、C1-C6烷基、氰基C1-C6烷基、羟基C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、氰基C3-C6环烷基、羟基C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烯基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、C3-C6环烷基C2-C6烯基、C3-C6环烷基C2-C6炔基、经取代或任选经R11取代的杂环基、未经取代或任选经R11取代的C6-C12芳基、未经取代或任选经R11取代的C5-C12杂芳基、未经取代或任选经R11取代的C7-C14芳烷基、未经取代或任选经R11取代的C6-C14杂芳烷基、羟基、C1-C6烷氧基、C1-C6卤代烷氧基、氰基C1-C6烷氧基、羟基C1-C6烷氧基、C1-C6卤代烷氧基C1-C6烷氧基、C1-C6烷氧基C1-C6卤代烷氧基、C1-C6卤代烷氧基C1-C6卤代烷氧基、C3-C6环烷氧基、C3-C6环烷基C1-C6烷氧基、C3-C6卤代环烷氧基、氰基C3-C6环烷氧基、C3-C6卤代环烷基C1-C6烷氧基、(氰基C3-C6环烷基)C1-C6烷氧基、C1-C6卤代烷基硫基C1-C6烷氧基、C1-C6卤代烷基亚磺酰基C1-C6烷氧基、C1-C6卤代烷基磺酰基C1-C6烷氧基、未经取代或任选经R11取代的C7-C14芳烷氧基、未经取代或任选经R11取代的C6-C14杂芳烷氧基、未经取代或任选经R11取代的C6-C12芳氧基、未经取代或任选经R11取代的C5-C12杂芳氧基、硫烷基、五卤代硫烷基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C3-C6环烷基硫基、C3-C6环烷基亚磺酰基、C3-C6环烷基磺酰基、C3-C6卤代环烷基硫基、C3-C6卤代环烷基亚磺酰基、C3-C6卤代环烷基磺酰基、C3-C6环烷基C1-C6烷基硫基、C3-C6环烷基C1-C6烷基亚磺酰基、C3-C6环烷基C1-C6烷基磺酰基、C3-C6卤代环烷基C1-C6烷基硫基、C3-C6卤代环烷基C1-C6烷基亚磺酰基、C3-C6卤代环烷基C1-C6烷基磺酰基、基团-S(R12)=NH、基团-S(R12)=N-C≡N、基团-S(R12)=N-C(=O)R13、基团-S(R12)(=O)=NH、基团-S(R12)(=O)=N-C≡N、基团-S(R12)(=O)=N-C(=O)R13、C6-C12芳基硫基、C6-C12芳基亚磺酰基、C6-C12芳基磺酰基、C5-C12杂芳基硫基、C5-C12杂芳基亚磺酰基、C5-C12杂芳基磺酰基、氨基、单(C1-C6烷基)氨基、二(C1-C6烷基)氨基、(二(C1-C6烷基)亚磺酰亚基)氨基、二(C1-C6烷基)磷酰基、C1-C7酰基、C1-C7卤代酰基、羟基亚氨基C1-C6烷基、羟基亚氨基(氨基)C1-C7烷基、C1-C6烷氧基亚氨基C1-C6烷基、C1-C6卤代烷氧基亚氨基C1-C6烷基、羧基、C1-C6烷氧基羰基、氨基羰基、单(C1-C6烷基)氨基羰基、二(C1-C6烷基)氨基羰基、单(C1-C6卤代烷基)氨基羰基、单(C3-C6环烷基)氨基羰基、单(氰基C3-C6环烷基)氨基羰基、单(C1-C6烷氧基亚氨基C1-C6烷基)氨基羰基、二(C1-C6烷基)氨基亚甲基氨基羰基、氨基硫羰基、单(C1-C6烷基)氨基硫羰基、二(C1-C6烷基)氨基硫羰基、或N-(C1-C6烷氧基)-N-(C1-C6烷基)氨基羰基,
R10表示氢原子、C1-C12烷基、C1-C6烷氧基C1-C6烷基、C1-C12卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C3-C6环烷基C2-C6炔基、C2-C6卤代炔基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、未经取代或任选经R11取代的杂环基C1-C6烷基、未经取代或任选经R11取代的C7-C14芳烷基、未经取代或任选经R11取代的C6-C14杂芳烷基、未经取代或任选经R11取代的C6-C12芳基、或未经取代或任选经R11取代的C5-C12杂芳基,
R11表示卤原子、叠氮基、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C6环烷基、五卤代硫烷基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、氨基、单(C1-C6烷基)氨基、或二(C1-C6烷基)氨基,及
R12及R13独立地表示C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基C1-C6卤代烷基、C1-C6卤代烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基C1-C6烷基、C3-C6卤代环烷基C1-C6烷基、氰基C1-C6烷基、未经取代或任选经R11取代的C7-C14芳烷基、或未经取代或任选经R11取代的C6-C14杂芳烷基。
2.如权利要求1所述的化合物或其盐,其中A7表示氮原子,且A8及A9分别表示经R8及R9取代的碳原子。
3.如权利要求1所述的化合物或其盐,其中A1表示键,
A2及A7分别表示氮原子,
W1表示氮原子,
W2表示碳原子,且
A3、A4、A5、A6、A8及A9分别表示经R3、R4、R5、R6、R8及R9取代的碳原子。
4.如权利要求3所述的化合物或其盐,其中R3、R4、R5、R6、R8及R9分别独立地表示氢原子、卤原子、C1-C6烷基、C1-C6卤代烷基、氰基C3-C6环烷基、C1-C6卤代烷氧基或氰基C1-C6烷氧基。
5.如权利要求1-4中任一项所述的化合物或其盐,其中R2表示C1-C6烷基。
6.如权利要求1-5中任一项所述的化合物或其盐,其中R10表示C1-C12卤代烷基。
7.如权利要求1所述的化合物或其盐,其中通式[I]表示的化合物为通式[Ia]表示的化合物,
式中,A2、A3、A4、A5、A6、A7、A8、A9、m、n、R1、R2及R10具有权利要求1中相同的定义。
8.如权利要求1所述的化合物或其盐,其中通式[I]表示的化合物为通式(A)表示的化合物,
式中,n、R3、R4、R5、R6及R10具有权利要求1中相同的定义。
9.如权利要求8所述的化合物或其盐,其中n为2,R3、R5及R6各自为氢原子,R4为C1-C6卤代烷基、氰基C3-C6环烷基、C1-C6卤代烷氧基、或氰基C1-C6烷氧基,且R10为C1-C12卤代烷基。
10.如权利要求1所述的化合物或其盐,其中通式[I]表示的化合物为通式(B)表示的化合物,
式中,R2、R4、R5及R10具有权利要求1中相同的定义。
11.如权利要求1所述的化合物或其盐,其中通式[I]表示的化合物为通式(C)表示的化合物,
式中,m、n、R1、R4、R5及R10具有权利要求1中相同的定义。
12.如权利要求1所述的化合物或其盐,其中通式[I]表示的化合物为通式(D)表示的化合物,
式中,A2、A3、A4、A5、A6及R10具有权利要求1中相同的定义。
13.如权利要求12所述的化合物或其盐,其中A2表示氮原子或经Rb取代的碳原子,A3表示氮原子或经R3取代的碳原子,且A4、A5及A6各自独立地表示氮原子或分别经R4、R5及R6取代的碳原子。
14.一种农药组合物,其含有权利要求1-13中任一项所述的化合物或其盐作为有效成分。
15.如权利要求14所述的农药组合物,其中该农药组合物进一步含有表面活性剂。
16.一种有害生物防治剂,其含有权利要求1-13中任一项所述的化合物或其盐作为活性成分。
17.如权利要求16所述的有害生物防治剂,其中该有害生物防治剂为杀虫剂、杀线虫剂及杀螨剂。
18.如权利要求17所述的有害生物防治剂,其对于在种植农业及园艺植物的水田、农地、草坪、果园、非农用地、温室、苗圃设施、植物工厂中的有害生物具有防治效果。
19.如权利要求18所述的有害生物防治剂,其中该农业及园艺植物是通过育种方法或基因重组技术已被赋予抗性的植物。
20.一种防治有害生物的方法,其使用有效量的权利要求1-13中任一项所述的化合物或其盐。
21.一种防治有害生物的方法,其通过将含有权利要求1-13中任一项所述的化合物或其盐作为有效成分的农药组合物同时或分次地作用于将种植或正在种植农作物或园艺作物的场所。
22.如权利要求20或21所述的防治有害生物的方法,其中该有害生物防治剂施用的场所为水田、农地、草坪、果园、非农用地、温室、苗圃设施或植物工厂。
23.如权利要求20-22中任一项所述的防治有害生物的方法,其中是以权利要求1-13中任一项所述的化合物或其盐作为杀虫剂、杀线虫剂及杀螨剂使用。
24.权利要求16-19中任一项所述的有害生物防治剂用于防治针对农作物或园艺作物的有害生物的用途。
25.如权利要求1所述的通式[I]表示的化合物或其盐,其中在通式[I]中的R10为氢原子。
26.一种制造权利要求1所述的通式[I]表示的化合物的方法,其特征为使用权利要求25所述的化合物或其盐作为原料。
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AU2002350217A1 (en) | 2001-12-04 | 2003-06-17 | Bristol-Myers Squibb Company | Glycinamides as factor xa inhibitors |
FR2928923B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques |
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WO2017061497A1 (ja) | 2015-10-06 | 2017-04-13 | 日本農薬株式会社 | 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
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