CN114524819A - 具有含硫取代基的杀有害生物活性多环衍生物 - Google Patents
具有含硫取代基的杀有害生物活性多环衍生物 Download PDFInfo
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- CN114524819A CN114524819A CN202210159356.4A CN202210159356A CN114524819A CN 114524819 A CN114524819 A CN 114524819A CN 202210159356 A CN202210159356 A CN 202210159356A CN 114524819 A CN114524819 A CN 114524819A
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- 125000001424 substituent group Chemical group 0.000 title claims abstract description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 20
- 229910052717 sulfur Inorganic materials 0.000 title claims description 19
- 239000011593 sulfur Substances 0.000 title claims description 16
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 367
- -1 Carboxyl group Chemical group 0.000 claims description 264
- 239000001257 hydrogen Substances 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 109
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 98
- 150000002431 hydrogen Chemical class 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 72
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000001188 haloalkyl group Chemical group 0.000 claims description 49
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000004480 active ingredient Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 241000607479 Yersinia pestis Species 0.000 claims description 25
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
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- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 230000000361 pesticidal effect Effects 0.000 claims description 7
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- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
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- 239000000575 pesticide Substances 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
- 241000244206 Nematoda Species 0.000 description 40
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 36
- 241000894007 species Species 0.000 description 36
- 108700012359 toxins Proteins 0.000 description 35
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- 239000003053 toxin Substances 0.000 description 33
- 231100000765 toxin Toxicity 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 31
- 241000196324 Embryophyta Species 0.000 description 30
- 239000000126 substance Substances 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000012043 crude product Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000014759 maintenance of location Effects 0.000 description 24
- 241000238631 Hexapoda Species 0.000 description 22
- 239000002585 base Substances 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 240000008042 Zea mays Species 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 238000011160 research Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 235000009973 maize Nutrition 0.000 description 16
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- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 14
- 239000002671 adjuvant Substances 0.000 description 14
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- 238000009472 formulation Methods 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011655 sodium selenate Substances 0.000 description 1
- 235000018716 sodium selenate Nutrition 0.000 description 1
- 229960001881 sodium selenate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- LOGJGKGBKZOEKZ-UHFFFAOYSA-N sordidin Natural products O1C2(C)CC(C)C1(CC)OC(C)C2 LOGJGKGBKZOEKZ-UHFFFAOYSA-N 0.000 description 1
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- 150000003871 sulfonates Chemical class 0.000 description 1
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
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- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BPJYAXCTOHRFDQ-UHFFFAOYSA-L tetracopper;2,4,6-trioxido-1,3,5,2,4,6-trioxatriarsinane;diacetate Chemical compound [Cu+2].[Cu+2].[Cu+2].[Cu+2].CC([O-])=O.CC([O-])=O.[O-][As]1O[As]([O-])O[As]([O-])O1.[O-][As]1O[As]([O-])O[As]([O-])O1 BPJYAXCTOHRFDQ-UHFFFAOYSA-L 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N tetradec-11-enyl acetate Chemical compound CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- KNDVJPKNBVIKML-UHFFFAOYSA-N tetraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(CN2N=C(N=N2)C(F)(F)F)=NN1C1=NC=CC=C1Cl KNDVJPKNBVIKML-UHFFFAOYSA-N 0.000 description 1
- 239000004577 thatch Substances 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IGOWHGRNPLFNDJ-UHFFFAOYSA-N tricos-9t-ene Natural products CCCCCCCCCCCCCC=CCCCCCCCC IGOWHGRNPLFNDJ-UHFFFAOYSA-N 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- XBRCDWHXULVEFB-UHFFFAOYSA-N triphenyltin(1+) Chemical compound C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 XBRCDWHXULVEFB-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 241001515965 unidentified phage Species 0.000 description 1
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- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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- 150000003739 xylenols Chemical class 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
具有化学式(I)的多环衍生物,
Description
本申请是发明名称为“具有含硫取代基的杀有害生物活性多环衍生物”的中国发明专利申请No.201680006282.3的分案申请,其申请日是2016年01月14日,优先权日是2015年01月19日。
本发明涉及包含硫取代基的杀有害生物活性(特别是杀虫活性)多环衍生物,涉及包含那些化合物的组合物,并且涉及它们用于控制动物有害生物(包括节肢动物并且特别是昆虫或蜱螨目的代表)的用途。
具有杀有害生物作用的杂环化合物是已知的并描述于例如WO 2012/086848、WO2013/018928、WO 2014/142292、WO 2015/133603、WO 2015/000715和WO 2015/121136中。现在已经发现具有包含硫的苯基和吡啶基取代基的新颖的杀有害生物活性多环的环衍生物。
本发明因此涉及具有化学式I的化合物,
其中
A表示CH、N或N-氧化物;
A1是CH、N或N-氧化物;
Q是可以被选自下组的取代基单取代或多取代的苯基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是五-元至十元单环的或稠合的双环的环系统,该环系统经由碳原子连接至包含基团A的环,所述环系统可以是芳香族的、部分饱和的或完全饱和的并且包含1至4个选自下组的杂原子,该组由以下各项组成:氮、氧和硫,其条件是每个环系统不能包含多于2个氧原子和多于2个硫原子,所述五-元至十元环系统可以被独立地选自下组的取代基单-取代至多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是部分饱和的或完全饱和的五元至六元芳香族环系统,该环系统经由氮原子连接至包含基团A的环,所述环系统可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;并且所述环系统包含1个、2个或3个选自下组的杂原子,该组由以下各项组成:氮、氧和硫,其条件是所述环系统不能包含多于一个氧原子和多于一个硫原子;或者
Q是C3-C6环烷基,或被选自下组的取代基单取代或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、CONH2、羧基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C2-C6烯基,或被选自下组的取代基单取代或多取代的C2-C6烯基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C2-C6炔基,或被选自下组的取代基单取代或多取代的C2-C6炔基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、三(C1-C4烷基)甲硅烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代-烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C1-C6烷基,或被选自下组的取代基单取代或多取代的C1-C6烷基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、三(C1-C4烷基)甲硅烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代-烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基;或者
R1是被选自下组的取代基单取代或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;或者
R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2是卤素、氰基、C1-C6卤代烷基或被一个或两个选自下组的取代基取代的C1-C6卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;或者
R2是C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、O(C1-C4卤代烷基)、或-C(O)C1-C4卤代烷基;或者
R2是可以被选自下组的取代基单取代或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;
X1是NR5;其中R5是氢、C1-C4烷基、C2-C6烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基;或者
X1是氧或硫;
R3是氢或C1-C2-烷基;
R4是氢、卤素或C1-C3卤代烷基;
以及具有化学式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体。
具有至少一个碱性中心的具有化学式I的化合物可以与以下酸形成例如酸加成盐,这些酸为:例如强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、磷酸或氢卤酸),强有机羧酸(例如未经取代的或像被卤素取代的C1-C4烷羧酸,例如乙酸(像饱和或不饱和的二羧酸),例如草酸、丙二酸、琥珀酸、马来酸、富马酸或邻苯二甲酸(像羟基羧酸),例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或像苯甲酸),或有机磺酸(例如未经取代的或像被卤素取代的C1-C4烷-或芳基磺酸,例如甲烷-或对甲苯磺酸)。具有至少一个酸性基团的具有化学式I的化合物可以例如与碱形成盐,例如矿物盐,例如碱金属或碱土金属盐,例如钠盐、钾盐或镁盐;或与氨或有机胺形成盐,例如吗啉、哌啶、吡咯烷、单、二或三低碳数烷基胺,例如乙胺、二乙胺、三乙胺或二甲基丙基胺,或单、二或三羟基低碳数烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺。
在取代基定义中出现的烷基基团可以是直链的或支链的,并且是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、以及它们的支链异构体。烷基硫烷基、烷基亚磺酰基、烷基磺酰基、烷氧基、烯基和炔基残基衍生自所提及的烷基残基。烯基和炔基基团可以是单不饱和的或多不饱和的。C1-二-烷基氨基是二甲基氨基。
卤素一般是氟、氯、溴或碘。相应地,这也适用于与其他含义结合的卤素,例如卤代烷基或卤代苯基。
卤代烷基基团优选地具有从1至6个碳原子的链长。卤代烷基是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基以及2,2,2-三氯乙基。
烷氧基是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基并且还是同分异构的戊氧基以及己氧基基团。
烷氧基烷基是例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
烷氧基羰基是例如甲氧基羰基(其为C1烷氧基羰基)、乙氧基羰基、丙氧基羰基、异丙氧基羰基、正丁氧基羰基、叔丁氧基羰基、正戊氧基羰基或己氧基羰基。
烷基硫烷基是例如甲基硫烷基、乙基硫烷基、丙基硫烷基、异丙基硫烷基、丁基硫烷基、戊基硫烷基、以及己基硫烷基。
烷基亚磺酰基是例如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、丁基亚磺酰基、戊基亚磺酰基、以及己基亚磺酰基。
烷基磺酰基是例如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、戊基磺酰基、以及己基磺酰基。
卤代烷基硫烷基是例如三氟甲基硫烷基、2,2,2-三氟乙基硫烷基、和五氟乙基硫烷基。
卤代烷基亚磺酰基是例如三氟甲基亚磺酰基、2,2,2-三氟乙基亚磺酰基、或五氟乙基亚磺酰基。
卤代烷基磺酰基是例如三氟甲基磺酰基、2,2,2-三氟乙基磺酰基、和五氟乙基磺酰基。
环烷基是例如环丙基、环丁基、环戊基和环己基。
在本发明的上下文中,经由氮原子连接至包含基团A的环的部分饱和的或完全饱和的五元至六元芳香族环系统的实例是例如吡唑、吡咯、吡咯烷、吡咯烷-2-酮、哌啶、吗啉、咪唑、三唑和吡啶-2-酮。
在本发明的上下文中,取代基定义中的“单取代的至多取代的”典型地是指取决于取代基的化学结构,单取代的至七次取代的,优选地是单取代的至五次取代的,更优选地是单、二或三取代的。
根据本发明的具有化学式I的化合物还包括在盐形成期间可以形成的水合物。
根据本发明,取决于环成员的数目,五-至十元单环或稠合双环杂环系统(该五至十元单环或稠合双环杂环系统可以是芳香族的、部分饱和的或完全饱和的,并且该五至十元单环或稠合双环杂环系统包含选自下组的1至4个杂原子,该组由以下各项组成:氮、氧和硫,其条件是每个环系统不可能包含多于2个氧原子以及多于2个硫原子),或三至十元单环或稠合双环环系统(该三至十元单环或稠合双环环系统可以是芳香族的、部分饱和的或完全饱和的),优选地选自下组,该组由以下杂环基团组成:
吡咯基;吡唑基;异噁唑基;呋喃基(furanyl);噻吩基;咪唑基;噁唑基;噻唑基;异噻唑基;三唑基;噁二唑基;噻二唑基;四唑基;呋喃基(furyl);吡啶基;嘧啶基;吡嗪基;哒嗪基;三嗪基,吡喃基;喹唑啉基;异喹啉基;吲嗪基;异苯并呋喃基萘啶基;喹喔啉基;噌啉基;酞嗪基;苯并噻唑基;苯并噁唑基;苯并三唑基;吲唑基;吲哚基;(1H-吡咯-1-基)-;(1H-吡咯-2-基)-;(1H-吡咯-3-基)-;(1H-吡唑-1-基)-;(1H-吡唑-3-基)-;(3H-吡唑-3-基)-;(1H-吡唑-4-基)-;(3-异噁唑基)-;(5-异噁唑基)-;(2-呋喃基)-;(3-呋喃基)-;(2-噻吩基)-;(3-噻吩基)-;(1H-咪唑-2-基)-;(1H-咪唑-4-基)-;(1H-咪唑-5-基)-;(2-噁唑-2-基)-;(噁唑-4-基)-;(噁唑-5-基)-;(噻唑-2-基)-;(噻唑-4-基)-;(噻唑-5-基)-;(异噻唑-3-基)-;(异噻唑-5-基)-;(1H-1,2,3-三唑-1-基)-;(1H-1,2,4-三唑-3-基)-;(4H-1,2,4-三唑-4-基)-;(1H-1,2,4-三唑-1-基)-;(1,2,3-噁二唑-2-基)-;(1,2,4-噁二唑-3-基)-;(1,2,4-噁二唑-4-基)-;(1,2,4-噁二唑-5-基)-;(1,2,3-噻二唑-2-基)-;(1,2,4-噻二唑-3-基)-;(1,2,4-噻二唑-4-基)-;(1,3,4-噻二唑-5-基)-;(1H-四唑-1-基)-;(1H-四唑-5-基)-;(2H-四唑-5-基)-;(2-吡啶基)-;(3-吡啶基)-;(4-吡啶基)-;(2-嘧啶基)-;(4-嘧啶基)-;(5-嘧啶基)-;(2-吡嗪基)-;(3-哒嗪基)-;(4-哒嗪基)-;(1,3,5-三嗪-2-基)-;(1,2,4-三嗪-5-基)-;(1,2,4-三嗪-6-基)-;(1,2,4-三嗪-3-基)-;(呋咱-3-基)-;(2-喹啉基)-;(3-喹啉基)-;(4-喹啉基)-;(5-喹啉基)-;(6-喹啉基)-;(3-异喹啉基)-;(4-异喹啉基)-;(2-喹唑啉基)-;(2-喹喔啉基)-;(5-喹喔啉基)-;(吡啶并[2,3-b]吡嗪-7-基)-;(苯并噁唑-5-基)-;(苯并噻唑-5-基)-;(苯并[b]噻吩-2-基)-和(苯并[1,2,5]噁二唑-5-基)-;二氢吲哚基以及四氢喹啉基。
在优选的具有化学式I的化合物中,Q选自下组,该组由J-0至J-50组成:
其中每个基团J-0至J-50被Rx单取代、二取代或三取代,其中
每个Rx独立地选自下组,该组由以下各项组成:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
具有化学式I的化合物的优选的组由具有化学式I-1的化合物表示
其中R2、R4、A、X和Q是如以上在化学式I下所定义的;并且其中R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R4是氢、卤素或C1-C3卤代烷基;X1是N-甲基、氧或硫;以及具有化学式I-1的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
在所述具有化学式I-1的化合物的优选的组中,R2优选地是C1-C4卤代烷基、卤素、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;X是SO2;R1优选地是乙基;X1优选地是N-甲基;并且R4优选地是氢或C1-C2卤代烷基。
在所述具有化学式I-1的化合物的优选的组中,Q选自下组,该组由以下各项组成:J-0至J-50(其中箭头表示杂环到基团Q的附着点):
其中每个基团J-0至J-50被Rx单取代、二取代或三取代,其中每个Rx独立地选自下组,该组由以下各项组成:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
另外优选的具有化学式I的化合物由具有化学式I-2的化合物表示
其中R2、R4、A、X和Q是如以上在化学式I下所定义的;并且其中R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R4是氢、卤素或C1-C3卤代烷基;X1是N-甲基、氧或硫;以及这些具有化学式I-2的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
在所述具有化学式I-2的化合物的优选的组中,R2优选地是C1-C4卤代烷基、卤素、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;X是SO2;R1优选地是乙基;X1优选地是N-甲基;并且R4优选地是氢或C1-C2卤代烷基。
在所述具有化学式I-2的化合物的优选的组中,Q选自下组,该组由以下各项组成:J-0至J-50(其中箭头表示杂环到基团Q的附着点):
其中每个基团J-0至J-50被Rx单取代、二取代或三取代,其中每个Rx彼此独立地选自下组,该组由以下各项组成:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
特别地,具有化学式I-1的优选化合物是具有化学式I-1a的那些
其中
A是N或CH;
X是S或SO2;
R1是C1-C4烷基;
R2是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
R4是氢或C1-C2卤代烷基;
Qa1选自下组,该组由以下取代基组成:
其中每个Rx彼此独立地选自下组,该组由以下各项组成:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
具有化学式I-1a的更优选的化合物是其中每个Rx彼此独立地选自氢、卤素、C1-C4烷基和C1-C4卤代烷基的那些。
具有化学式I-1a的化合物的尤其优选的组由具有化学式I-1a2的化合物表示
其中
A是N或CH;
R2是C1-C2卤代烷基、C1-C2卤代烷基硫烷基、C1-C2卤代烷基亚磺酰基或C1-C2卤代烷基磺酰基;
R4是氢或C1-C2卤代烷基;
并且Qa1选自下组,该组由以下取代基组成
其中每个Rx彼此独立地是氢、卤素、C1-C4烷基或C1-C4卤代烷基。
在所述具有化学式I-1a2的优选的化合物中,Rx彼此独立地优选为卤素、氢或C1-C4卤代烷基;R1优选地是乙基;并且R4优选地是氢。
特别地,具有化学式I-1a2的优选的化合物是其中Qa1选自J-0z1、J-0z2、J0z3、J-1Z、J-5Z、J-30Z和J-43Z的那些;
其中每个Rx彼此独立地是氢、卤素或C1-C4卤代烷基。
具有化学式I-2的更高度优选的化合物是具有化学式I-2a的那些化合物
其中
A是N或CH;
X是S或SO2;
R1是C1-C4烷基;
R2是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
R4是氢或C1-C1-C2卤代烷基;
Qa1优选地选自下组,该组由以下取代基组成
其中每个Rx彼此独立地选自:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
具有化学式I-2a的更优选的化合物是其中每个Rx彼此独立地选自氢、卤素、C1-C4烷基和C1-C4卤代烷基的那些;
具有化学式I-2a的化合物的尤其优选的组由具有化学式I-2a2的化合物表示
其中
A是N或CH;
R2是C1-C2卤代烷基、C1-C2卤代烷基硫烷基、C1-C2卤代烷基亚磺酰基或C1-C2卤代烷基磺酰基;
R4是氢或C1-C2卤代烷基;
并且Qa1选自以下取代基的组;
其中每个Rx彼此独立地是氢、卤素、C1-C4烷基或C1-C4卤代烷基。
在所述具有化学式I-2a2的优选的化合物中,每个Rx彼此独立地优选为卤素、氢或C1-C4卤代烷基;R1优选地是乙基;并且R4优选地是氢。
具有化学式I-2a2的最高度优选的化合物是其中Qa1选自J-0z1、J-0z2、J0z3、J-1Z、J-5Z、J-30Z和J-43Z的那些;
其中每个Rx彼此独立地是氢、卤素或C1-C4卤代烷基。
在以上提到的具有化学式I的化合物的所有优选的实施例中,取代基Q和Qa1优选地选自
a)苯基,其可以被卤素或C1-C4卤代烷基取代;
b)吡唑,其可以被C1-C4卤代烷基取代;
d)环丙基,其可以被氰基取代;
e)三唑,其可以被卤素取代;
f)C2-C6炔基,其可以被苯基取代,其中所述苯基可以被卤素取代;以及
g)C2-C6烯基,其可以被苯基取代,其中所述苯基可以被卤素取代。
具有化学式I的化合物的特别优选的实施例由具有化学式I-2a3的化合物表示
其中
R2是C1-C4卤代烷基;
R4是氢或C1-C4烷基;并且
Q选自
a)苯基,其可以被卤素或C1-C4卤代烷基取代;
b)吡唑,其可以被C1-C4卤代烷基取代;
d)环丙基,其可以被氰基取代;
e)三唑,其可以被卤素取代;
f)C2-C6炔基,其可以被苯基取代,其中所述苯基可以被卤素取代;以及
g)C2-C6烯基,其可以被苯基取代,其中所述苯基可以被卤素取代。
在本发明的另外的实施例中,具有化学式I的化合物是优选的,其中
R1是C1-C4烷基;
R2是C1-C4卤代烷基或C1-C4卤代烷基硫烷基;
R3是氢;
R4是氢或C1-C4卤代烷基;
Q是苯基,该苯基可以被选自下组的取代基单取代、二取代或三取代,该组由以下各项组成:卤素和C1-C4卤代烷基;或者
Q是C2-C6烯基,该Q是C2-C6烯基可以被苯基单取代,该苯基本身可以被C1-C4卤代烷基单取代;或者
Q是吡唑基,该吡唑基可以被C1-C4卤代烷基或卤素单取代;或者
Q是嘧啶基或C3-C6环烷基,所述环烷基可以被氰基取代;或者
Q是三唑基,该三唑基可以被卤素取代;或者
Q是C1-C4烷基,该C1-C4烷基可以被氰基取代;或者
Q是C2-C6炔基,该C2-C6炔基可以被苯基单取代,该苯基本身可以被卤素单取代或二取代;
X是S或SO2;
X1是N-C1-C4烷基;特别是N-CH3;
A是CH或N;并且
A1是CH或N。
根据本发明的用于制备具有化学式I的化合物的方法原则上通过本领域普通技术人员已知的方法来进行,并且如下所述:
具有化学式I的化合物(其中A、A1、R2、R1、R3、R4、X、X1和Q是如在化学式I中所定义的)可以通过铃木反应来制备(如方案1中所示的),该铃木反应涉及例如使具有化学式II的化合物(其中Xb1是离去基团,例如氯、溴或碘,或芳基-或烷基磺酸酯如三氟甲磺酸酯)与具有化学式IIIa的化合物(其中Yb1可以是硼衍生的官能团,如例如B(OH)2或B(ORb1)2,其中Rb1可以是C1-C4烷基基团或两个基团ORb1可以与硼原子一起形成五元环,如例如频哪醇硼酸酯)进行反应。该反应可以通过基于钯的催化剂例如四(三苯基膦)-钯或(1,1'双(二苯基膦基)-二茂铁)二氯化钯-二氯甲烷(1:1络合物),在碱(像碳酸钠或氟化铯)的存在下,在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的或者二噁烷和水的混合物)中,优选在惰性气氛下来催化。反应温度的范围可以优先是从室温到反应混合物的沸点。此类铃木反应是本领域技术人员熟知的,并且已经综述于例如有机金属化学杂志(J.Orgmet.Chem.)576,1999,147-168中。
方案1:
可替代地,具有化学式I的化合物可以通过具有化学式IIIb的化合物(其中Yb2是三烷基锡衍生物,优选三正丁基锡)与具有化学式II的化合物的施蒂勒反应来制备。此类施蒂勒反应通常是在钯催化剂例如四(三苯基膦)钯(0)、或(1,1'双(二苯基膦基)-二茂铁)二氯化钯-二氯甲烷(1:1络合物)的存在下,在惰性溶剂如DMF、乙腈、或二噁烷中,任选地在添加剂如氟化铯或氯化锂的存在下,并且任选地在另外的催化剂例如碘化铜(I)的存在下进行。此类施蒂勒偶联也是本领域技术人员熟知的,并且已经描述于例如有机化学杂志(J.Org.Chem.),2005,70,8601-8604,有机化学杂志(J.Org.Chem.),2009,74,5599-5602,以及应用化学国际版本(Angew.Chem.Int.Ed.),2004,43,1132-1136中。
具有化学式I的化合物(其中Q是携氮杂环系统,并且其中A、A1、R2、R1、R3、R4、X、X1和Q是如在化学式I中所定义的)可以通过使杂环Q(其包含适当的NH官能度)在碱(例如碱金属氢化物如氢化钠,或碱金属碳酸盐例如碳酸铯或碳酸钾)存在下,任选地在铜催化剂(例如碘化铜(I))存在下,在惰性溶剂(如N-甲基吡咯二酮或DMF)中,在30℃-150℃之间的温度下进行反应而从具有化学式II的化合物(其中A、A1、R2、R1、R3、R4、X和X1是如在化学式I中所定义的,并且Xb1是离去基团如氯、溴或碘,或芳基-或烷基磺酸酯如三氟甲磺酸酯)制备。该反应特别有利于其中A是甲烷的具有化学式I的化合物。可替代地,这样的化合物可以通过使杂环Q(其包含适当的NH官能度)在碱(例如碱金属氢化物如氢化钠,或碱金属碳酸盐例如碳酸铯或碳酸钾)存在下,在适合的溶剂(如N-甲基吡咯二酮或DMF)中,在30℃-150℃之间的温度下进行反应而从具有化学式II的化合物制备。针对杂环J-30Z,在方案2中对该反应进行了说明,该反应给出了具有化学式Iaa的化合物(其中A、A1、R2、R1、R3、R4、X和Rx是如先前所定义的)。
方案2
具有化学式I的化合物也可以通过如上所述的铃木反应来制备(如在方案3中所描绘的),该反应涉及使具有化学式IV的化合物与具有化学式V的化合物进行反应,其中Xb2可以是卤素(优先地是氯、溴、或碘)或磺酸酯(像例如三氟甲磺酸酯),并且Yb3可以是硼衍生的官能团(如例如B(OH)2或B(ORb2)2,其中Rb2可以是C1-C4烷基基团或两个基团ORb2可以与硼原子一起形成五元环(如例如频哪醇硼酸酯))。在化学式IV中,A、A1、X、X1、R1、R2、R3和R4是如在化学式I中所述的。
该反应可以通过基于钯的催化剂(例如四(三苯基膦)钯),在碱(像碳酸钠)的存在下,在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的混合物)中,优选地在惰性气氛下进行催化。该反应温度可以优先地在室温至反应混合物的沸点的范围内。
方案3
以类似方式,具有化学式I的化合物可以在如方案1中所描述的条件下通过具有化学式V的化合物与具有化学式VI的化合物(其中A、A1、A2、X、X1、R1、R2、R3和R4是如上所述的,并且Yb4是三烷基锡衍生物,优选三正丁基锡)的施蒂勒偶联来制备(方案3)。
具有化学式IIa的化合物(其中A是氮并且A1、X1、R1、R2、R3和R4是如在化学式I中所描述的,并且Xb1是氯或溴)可以根据方案4所示的方法来制备:
方案4.
因此,将具有化学式IVa的化合物通过本领域技术人员已知的并且例如在WO2010/125985中所描述的方法氧化,以给出具有化学式VIIa的化合物,其中A1、X1、R1、R2、R3和R4是如在化学式I中所描述的,并且Xb1是氯或溴。任选地在碱(如三乙胺)存在下,并且任选地在溶剂(例如二氯甲烷、DMF或二噁烷)中,用三氯氧磷或三氯氧磷处理具有化学式VIIa的化合物(参见例如,合成通讯(Syn.Comm.),31(16),2507-2511,2001)其中A是CH的具有化学式II的化合物,即具有化学式IIb的化合物,可以如方案5所示制备:
方案5.
因此,可以例如用溴或氯,在适当的溶剂(例如冰醋酸)中,在0℃和150℃之间的温度下,任选地在微波反应器中将具有化学式IVb的化合物卤化成具有化学式VIIb的化合物,其中A1、X1、R1、R2、R3和R4是如在化学式I中所描述的并且Xb1是氯或溴。可替代地,可以在路易斯酸催化剂例如三氯化铁或三氯化铝存在下进行该反应(弗里德尔-克拉夫茨(Friedel-Crafts)卤化)。类似的反应已经在文献中描述(参见例如,Ger.Offen.,19840337,2000;药物化学快报(Med.Chem.Lett.),3(6),450-453,2012和大分子(Macromolecules),47(14),4607-4614,2014)。根据本领域技术人员已知的和例如在WO 2010/125985中描述的方法氧化VIIb产生具有化学式IIb的化合物,其中A1、X1、R1、R2、R3和R4是如在化学式I中所描述的并且Xb1是氯或溴。
具有化学式I的化合物也可以通过使具有化学式VIII的化合物,
(其中X、R1、R3、R4、Q和A是如以上在化学式I下所描述的),与具有化学式IX的化合物,
(其中A1和R2是如以上在化学式I下所描述的,并且其中R5是氢或如以上在化学式I下所描述的),在脱水剂(例如像多磷酸)存在下,在150℃至250℃之间的温度下进行反应,以产出具有化学式I的化合物,其中这些取代基是如以上和在化学式I下所描述的。这些方法是熟知的,并已描述于例如WO 2008/128968,WO 2012/086848,WO 2013/018928,WO2014/142292和WO 2006/003440中。针对具有化学式Ia的化合物,该方法概述于方案6中:
方案6
如在方案6中可见的,具有化学式Ia的化合物的形成通过具有化学式X的化合物(和/或其位置异构体Xa)的中间状态而发生。中间体X或中间体Xa可以作为纯实体而形成,或者中间体X和Xa可以作为区域异构的酰化产物的混合物而产生。在许多情况下,有利的是通过此类中间体X/Xa这样制备具有化学式(Ia)的化合物,这些中间体可以是经分离且任选地经纯化的。针对具有化学式Ia的化合物,在方案7中对此进行了说明:
方案7
具有化学式X和/或Xa的化合物(或其混合物)或其盐(其中Q是如以上所定义的,并且其中X、R1、R2、R3、R4、A和A1是如以上在化学式I下所描述的,并且其中R5是氢或如以上在化学式I下所描述的)可以通过以下方式来制备
i)通过本领域技术人员已知且描述于例如四面体(Tetrahedron),2005,61(46),10827-10852中的方法活化具有化学式VIII的化合物(其中Q是如以上所定义的),以形成经活化的种类VIIIa(其中Q是如以上所定义的并且其中X01是卤素,优选氯)。例如,通过在催化量的N,N-二甲基甲酰胺(DMF)存在下,在惰性溶剂(如二氯甲烷或四氢呋喃)中,在20℃至100℃之间的温度(优选25℃)下,用例如草酰氯(COCl)2或亚硫酰氯SOCl2处理VIII来形成化合物VIIIa(其中X01是卤素,优选地是氯)。可替代地,在惰性溶剂(如吡啶或四氢呋喃)中,任选地在碱(如三乙胺)存在下,在25℃-180℃之间的温度下,用例如1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)或二环己基碳二亚胺(DCC)处理具有化学式VIII的化合物,将产生活化的种类VIIIa(其中X01分别是随后
ii)在0℃至80℃的温度下,在惰性溶剂(如二氯甲烷、四氢呋喃、二噁烷或甲苯)中,任选在碱(如三乙胺或吡啶)存在下,将活化的种类VIIIa用具有化学式IX的化合物(或其盐)(其中A1和R2如以上在化学式I下所描述的,并且R5是氢、C1-C4烷基、C2-C6烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基),处理,以形成具有化学式X和/或Xa的化合物(或其混合物)。
具有化学式X和/或Xa的化合物(或其混合物)可以进一步通过脱水而被转化为具有化学式Ia的化合物(其中Q如上所定义,并且其中A、A1、R1、R2、R3和R4是如以上在化学式I下所描述的,并且其中R5是氢或如以上在化学式I下所描述的),例如通过在酸催化剂(例如像甲磺酸、或对甲苯磺酸(TsOH))存在下,在惰性溶剂(如N-甲基吡咯烷)中,在25℃-180℃(优选100℃-170℃)之间的温度下,任选地在微波条件下加热化合物X和/或Xa(或其混合物),或通过在乙酸中在100℃-180℃之间的温度下加热。此类方法先前已经描述于例如WO2010/125985和WO 2015/000715中。通过使用本领域技术人员已知的条件水解具有化学式VIIIb、VIIIc和VIIId的化合物(见下文)来获得具有化学式VIII的化合物。方案8中说明了具有化学式I的化合物的替代合成。
方案8.
如方案8所示,具有化学式XII的化合物(其中R1、R4是如在化学式I中所描述的并且Xb3是卤素)可以与具有IIIa(铃木反应)或IIIb的化合物,如先前在方案1中所描述地进行反应,以给出具有化学式VIIIb的化合物。可替代地,在碱存在下,任选在铜催化剂存在下,具有化学式XII的化合物可以与具有化学式XIII的化合物(其中Q是杂环,并且氢与该杂环的氮原子附接)进行反应。该化学方法与方案2中所说明的方法相似。然后在适合的溶剂(例如甲醇或乙醇)中用氨处理具有化学式VIIIb的化合物,以给出具有化学式XI的酰胺,其中R1、R4和Q是如在化学式I中所描述的。将具有化学式XI的酰胺与具有化学式IXa的化合物(其中A1、R2和X1是如在化学式I中所描述的)进行反应,产生具有化学式Xc的化合物。这种酰胺氮杂芳基化反应通常在过渡金属催化的C-N键形成条件下进行,这些条件涉及催化体系(例如像[1,1'-双(二苯基膦基)二茂铁]二氯钯(II)),该催化体系通常由以下组成:金属如钯源(例如钯(0)前体,像Pd2(二亚苄基丙酮)3,或钯(II)前体,像Pd(OAc)2)和配体(例如基于膦的或基于N-杂环卡宾的);碱如醇盐(例如叔丁醇钠或叔丁醇钾),碳酸盐、磷酸盐或甲硅烷基酰胺(例如碳酸钾或碳酸铯、磷酸钾或六甲基二硅氮烷锂)或氢氧化物(例如氢氧化钠或氢氧化钾);以及溶剂如甲苯、四氢呋喃、二噁烷、二甲氧基乙烷、N,N-二甲基甲酰胺、N-甲基吡咯烷酮和二甲基亚砜、以及它们的水性溶液。这些方法是本领域技术人员已知的,并且描述于例如WO 2014/142292中。在上述那些酰胺交叉偶联反应条件下,具有化学式Xc的化合物可以进行分离,并转化成如方案7)中所述的具有化学式Ib的化合物,但也可以自发地闭环成具有化学式Ib的化合物,特别是在其中X1是NR5的情况下。可以通过本领域技术人员已知的方法,例如用间氯过苯甲酸在惰性溶剂(如氯仿或二氯甲烷)中来实现具有化学式Ib的化合物氧化为具有化学式I的化合物。可替代地,可以改变反应顺序使具有化学式XI的化合物首先被氧化成具有化学式XIa的化合物,并且然后使用前述相同的反应转化成具有化学式I的化合物。具有化学式XIIa和XIIb的化合物可以通过方案9和10中所示的反应获得。
方案9.
方案10
在方案9中,具有化学式XIV的化合物(其中R001是C1-C4烷基)可以被氧化,并且使用方案4中所述的方法将具有化学式XV的N-氧化物转化为具有化学式XII的化合物。类似地,具有化学式XIVa的化合物(其中R001是C1-C4烷基)可以被卤化成具有化学式XVa的化合物,并且然后使用方案5中所述的化学方法转化成具有化学式XIIb的化合物。具有化学式IV的化合物在文献中(例如在WO 2015/000715中)是已知的。具有化学式XIV和XIVa的化合物已经描述于例如WO 2014132971、WO 2014123205、WO 2014119670、WO 2014119679、WO2014119674、WO 2014119699、WO 2014119672和WO 2014104407中。具有化学式IXa的化合物或在文献中描述(参见例如WO 2014/142292)或是可商购的。
可以通过上文描述的方法制备具有化学式I的化合物(其中Q是C3-C6环烷基或被选自下组的取代基单取代或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和苯基)(具体而言,可以通过根据在方案1中做出说明的涉及环丙基-硼酸的铃木反应制备具有化学式I的化合物(其中Q是环丙基))。对于具有化学式I的化合物(其中Q是被氰基取代的C3-C6环烷基(例如化合物Iaaa)和被C1-C4卤代烷基取代的C3-C6环烷基(例如化合物Iaab))的具体情况,可以通过在方案11中示出的方法来制备这些化合物。
方案11
如方案11所示,在氟化锌(II)ZnF2、和钯(0)催化剂(如三(二亚苯基丙酮)二钯(0)-氯仿加合物(Pd2(dba)3))与配体(例如Xantphos)的存在下,在惰性溶剂(如N,N-二甲基甲酰胺DMF)中,在100℃-180℃之间的温度下,任选地在微波加热下,将具有化学式II的化合物(其中X是S、SO或SO2(具体地是SO2),并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且Xb1是离去基团(像例如氯、溴或碘(优选溴))或芳基磺酸酯或烷基磺酸酯如三氟甲磺酸酯)用三甲基甲硅烷基-乙腈(TMSCN)处理,产生具有化学式Iaaa的化合物(其中X是S、SO或SO2(具体地是SO2))。已经在文献,例如在有机快报(Org.Lett.),16(24),6314-6317;2014中描述了此类化学方法。可以在碱(如氢化钠、碳酸钾K2CO3或碳酸铯Cs2CO3)存在下,在惰性溶剂(如N,N-二甲基甲酰胺DMF、丙酮或乙腈)中,在0℃-120℃之间的温度下,用具有化学式XVII的化合物(其中Qx是直接键或者是(CH2)n,并且n是1、2或3,并且其中Xb10是离去基团如卤素(优选地是氯、溴或碘))处理具有化学式Iaaa的化合物以给出具有化学式Iaab的化合物(其中X是S、SO或SO2(具体地SO2),并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)。可替代地,可以通过在催化剂(如Pd2(dba)3)与配体(如BINAP)、强碱(如六甲基二硅氮烷锂LiHMDS)存在下,在惰性溶剂(如四氢呋喃THF)中,在30℃-80℃之间的温度下,用具有化学式XVI的化合物(其中Qx是如在XVII中所描述的)处理而直接从具有化学式II的化合物来制备具有化学式Iaa的化合物。已经在例如美国化学会志(J.Am.Chem.Soc.),127(45),15824-15832,2005中描述了此类化学方法。
具有化学式Iaab的化合物可以进一步用于制备具有化学式Iaac和Iaad的化合物(方案15)。实际上,在本领域技术人员已知的条件(水性碱性或酸性条件;例如,氢氧化锂或氢氧化钠在醇溶剂如甲醇中,在20℃至回流条件之间的温度)下,可以将具有化学式Iaab的化合物(其中X是S、SO或SO2,并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)水解为具有化学式Iaac的化合物(其中X是S、SO或SO2,并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)。任选地在氟化氢HF的存在下,在20℃-100℃之间的温度下,用试剂(如四氟化硫SF4或Fluolead(4-叔丁基-2,6-二甲基苯基三氟化硫))处理具有化学式Iaac的化合物产生具有化学式Iaad的化合物(其中X是S、SO或SO2,并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)。
具有化学式Iaab的化合物也可以用于制备具有化学式Iaae的化合物(方案12)。
方案12
如方案12所示,在本领域技术人员已知的条件(水性碱性或酸性条件;例如,氢氧化锂或氢氧化钠在醇溶剂如甲醇中,在20℃至回流条件之间的温度;或水性硫酸,任选地在共溶剂存在下,在20℃至回流条件之间的温度)下,可以将具有化学式Iaab的化合物(其中X是S、SO或SO2,并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)水解为具有化学式Iaae的化合物(其中X是S、SO或SO2,并且其中A1、A、X1、R1、R2、R3和R4是如上文所定义的,并且其中Qx是直接键或是(CH2)n,并且n是1、2或3)。
可替代地,可按如方案13和14中所示的来制备具有化学式Iaab的化合物。如在方案13中所示的,所使用的化学方法与在方案11中所描述的化学方法相同,只是反应的底物不同。因此,使先前描述的化合物XIIa和/或XIIb(其中X是S或SO2(具体地SO2),并且其中A、R1、R3和R4是如上文所定义的,并且其中Xb3是卤素(像例如,氯、溴或碘(优选地氯)或芳基-或烷基磺酸酯(如三氟甲磺酸酯)并且其中R0001是C1-C4烷基)与如在方案11中描述的三甲基甲硅烷基-乙腈TMSCN进行反应,产生具有化学式XVIII的化合物(其中X是S或SO2(具体地SO2),并且其中A、R1、R3和R4是如上文所定义的,并且其中R001是C1-C4烷基)。将这些通过与在方案11中描述的具有化学式XVII的化合物进行反应,转化为具有化学式VIIId的化合物(其中X是S或SO2(具体地SO2),并且其中Qx、A、R1、R3和R4是如上文所定义的,并且其中R001是C1-C4烷基)。通过本领域普通技术人员已知的方法将具有化学式VIIId的化合物容易地水解以给出具有化学式VIIIe的化合物(其中X是S或SO2(具体地SO2),并且其中Qx、A、R1、R3和R4是如上文所定义的)。
方案13
先前已经详细描述了方案14中所示的化学方法(参见例如,方案7)。此化学方法涉及形成被活化种类VIIIf(其中X是S或SO2(具体地SO2),并且其中Qx、A、R1、R3和R4是如上文所定义的,并且其中LG1典型地是氯),随后与具有化学式IXb的化合物(其中X1、A1和R2是如先前所定义的)酰胺偶联,以给出具有化学式Xd的化合物。可以通过先前在方案7中所描述的正式脱水(formaldehydration)步骤进而将那些具有化学式Xd的化合物转化为具有化学式Iaab的化合物。方案14中的所有取代基定义是如先前所描述的。
方案14
反应物可以在碱的存在下进行反应。适合的碱的实例是碱金属或碱土金属氢氧化物、碱金属或碱土金属氢化物、碱金属或碱土金属酰胺、碱金属或碱土金属醇盐、碱金属或碱土金属乙酸盐、碱金属或碱土金属碳酸盐、碱金属或碱土金属二烷基酰胺或碱金属或碱土金属烷基甲硅烷基酰胺、烷基胺、亚烷基二胺、游离的或N-烷基化的饱和或不饱和的环烷基胺、碱性杂环、氢氧化铵以及碳环胺。可以提及的实例是氢氧化钠、氢化钠、氨基钠、甲醇钠、乙酸钠、碳酸钠、叔丁醇钾、氢氧化钾、碳酸钾、氢化钾、二异丙氨基锂、双(三甲基硅烷基)酰胺钾、氢化钙、三乙胺、二异丙基乙胺、三亚乙基二胺、环己胺、N-环己基-N,N-二甲胺、N,N-二乙苯胺、吡啶、4-(N,N-二甲氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基铵氢氧化物以及1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
这些反应物可以按照原样彼此进行反应,即:不用添加溶剂或稀释剂。然而,在大多数情况下,添加一种惰性溶剂或稀释剂或这些的混合物是有利的。如果该反应在碱的存在下进行,那么这些过量使用的碱(如三乙胺、吡啶、N-甲基吗啉或N,N-二乙苯胺)还可以充当溶剂或稀释剂。
该反应有利地是在从约-80℃到约+140℃,优选从约-30℃到约+100℃,在许多情况下在介于环境温度与约+80℃之间的温度下进行。
具有化学式I的化合物能以本身已知的方法转化为另一种具有化学式I的化合物,这是通过以常规方式将具有化学式I的起始化合物的一个或多个取代基用根据本发明的另一个或其他或多个取代基的替代来实现的。
取决于所选的适合各自情况的反应条件以及起始材料,有可能例如,在一个反应步骤中仅将一个取代基用根据本发明的另一个取代基替代,或者在同一个反应步骤中可以将多个取代基用多个根据本发明的其他取代基来替代。
具有化学式I的化合物的盐能以本身已知的方式进行制备。因此,例如,具有化学式I的化合物的酸加成盐是通过用适合的酸或合适的离子交换试剂进行处理来获得的,并且与碱的盐是通过用适合的碱或用合适的离子交换试剂进行处理来获得的。
具有化学式I的化合物的盐能以常规方式转化为游离的化合物I、酸加成盐(例如通过用合适的碱性化合物或用合适的离子交换试剂进行处理)以及碱盐(例如通过用合适的酸或用合适的离子交换试剂进行处理)。
具有化学式I的化合物的盐能以本身已知的方式转化为具有化学式I的化合物的其他盐、酸加成盐,例如转化为其他酸加成盐,例如通过在合适的溶剂中用酸的合适的金属盐(如钠盐、钡盐或银盐,例如用乙酸银)来处理无机酸的盐(如盐酸盐),在该溶剂中,所形成的无机盐(例如氯化银)是不溶的并且因此从该反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的这些具有化学式I的化合物能以游离形式或盐的形式获得。
根据分子中存在的不对称碳原子的数目、绝对和相对构型和/或根据分子中存在的非芳香族双键的构型,在每种情况下为游离形式或为盐形式的具有化学式I的化合物和适当时其互变异构体可以可能的异构体之一的形式或作为其混合物存在,例如以纯异构体的形式,如对映体和/或非对映体,或作为异构体混合物,如对映异构体混合物,例如外消旋体、非对映体混合物或外消旋体混合物存在;本发明涉及纯异构体以及所有可能的异构体混合物,并且在上文和下文中都应如此理解,即使立体化学细节未在所有情况下明确提及。
处于游离形式或处于盐形式的具有化学式I的化合物的非对映异构体混合物或外消旋体混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或层析法以已知的方式分离成纯的非对映异构体或外消旋体。
能够以类似方式获得的对映异构体混合物(例如外消旋体)可以通过已知方法拆分成光学对映体,例如通过从光学活性溶剂再结晶;通过在手性吸附剂上的层析法,例如在乙酰纤维素上的高效液相层析法(HPLC);借助于合适的微生物,通过用特异性固定化酶裂解;通过形成包含化合物,例如使用手性冠醚,其中仅一个对映异构体被络合;或通过转化成非对映异构盐,例如通过使碱性最终产物外消旋体与光学活性酸(例如羧酸,例如樟脑酸、酒石酸或苹果酸或磺酸,例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而获得非对映异构体,从这些非对映异构体可以通过合适的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离合适的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明利用合适的立体化学的起始材料进行该方法。
可以通过使具有化学式I的化合物与适合的氧化剂(例如H2O2/尿素加合物)在酸酐(例如三氟乙酸酐)的存在下进行反应来制备N-氧化物。这样的氧化从文献,例如从药物化学杂志(J.Med.Chem.),32(12),2561-73,1989或WO 00/15615中已知。
有利的是在每一情况中分离或合成生物学地更有效的异构体,例如对映异构体或非对映异构体或异构体混合物,例如对映异构体混合物或非对映异构体混合物,如果个别组分具有不同的生物活性。
具有化学式I的化合物和适当时其互变异构体(在每种情况下处于游离形式或处于盐形式)如果适当的话还能以水合物的形式获得和/或包括其他溶剂,例如可以用于使以固体形式存在的化合物结晶的那些。
根据以下表1到6的化合物可以根据上述方法来制备。随后的这些实例旨在说明本发明并且展示优选的具有化学式I的化合物。
表X:该表披露了对于化学式(Iaa)、(Iab)、(Iac)、(Iad)、(Iae)和(Iaf)的33个取代基指定为X.001至X.033,这些化学式在表X之后披露。
表1:该表披露了具有化学式(Iaa)的33种化合物1.001至1.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物1.004具有以下结构:
表2:
该表披露了具有化学式(Iaa)的33种化合物2.001至2.033,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表3:
该表披露了具有化学式(Iaa)的33种化合物3.001至3.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表4:
该表披露了具有化学式(Iaa)的33种化合物4.001至4.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表5:
该表披露了具有化学式(Iaa)的33种化合物5.001至5.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表6:
该表披露了具有化学式(Iaa)的33种化合物6.001至6.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表7:
该表披露了具有化学式(Iaa)的33种化合物7.001至7.033,其中n是0,并且R2是OCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表8:
该表披露了具有化学式(Iaa)的33种化合物8.001至8.033,其中n是2,并且R2是OCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表9:
该表披露了具有化学式(Iaa)的33种化合物9.001至9.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表10:
该表披露了具有化学式(Iaa)的33种化合物10.001至10.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表11:
该表披露了具有化学式(Iaa)的33种化合物11.001至11.033,其中n是0,并且R2是SOCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表12:
该表披露了具有化学式(Iaa)的33种化合物12.001至12.033,其中n是2,并且R2是SOCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表13:
该表披露了具有化学式(Iaa)的33种化合物13.001至13.033,其中n是0,并且R2是SO2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表14:
该表披露了具有化学式(Iaa)的33种化合物14.001至14.033,其中n是2,并且R2是SO2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表15:
该表披露了具有化学式(Iaa)的33种化合物15.001至15.027,其中n是0,并且R2是Br,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表16:
该表披露了具有化学式(Iaa)的33种化合物16.001至16.033,其中n是2,并且R2是Br,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表17:
该表披露了具有化学式(Iaa)的33种化合物17.001至17.033,其中n是0,并且R2是CF2CH3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表18:
该表披露了具有化学式(Iaa)的33种化合物18.001至18.033,其中n是2,并且R2是CF2CH3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表19:
该表披露了具有化学式(Iaa)的33种化合物19.001至19.033,其中n是0,并且R2是OCF2CHFCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表20:
该表披露了具有化学式(Iaa)的33种化合物20.001至20.033,其中n是2,并且R2是OCH2CHFCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表21:
该表披露了具有化学式(Iaa)的33种化合物21.001至21.033,其中n是0,并且R2是OCH2CHF2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表22:
该表披露了具有化学式(Iaa)的33种化合物22.001至22.033,其中n是2,并且R2是OCH2CHF2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表23:
该表披露了具有化学式(Iaa)的33种化合物23.001至23.033,其中n是0,并且R2是C(CF3)2OCH3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表24:
该表披露了具有化学式(Iaa)的33种化合物24.001至24.033,其中n是2,并且R2是C(CF3)2OCH3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表25:
该表披露了具有化学式(Iaa)的33种化合物25.001至25.033,其中n是0,并且R2是CF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表26:
该表披露了具有化学式(Iaa)的33种化合物26.001至26.024,其中n是2,并且R2是CF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表27:
该表披露了具有化学式(Iaa)的33种化合物27.001至27.033,其中n是0,并且R2是CF2CH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表28:
该表披露了具有化学式(Iaa)的28种化合物28.001至28.033,其中n是2,并且R2是CF2CH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表29:
该表披露了具有化学式(Iaa)的27种化合物29.001至29.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表30:
该表披露了具有化学式(Iaa)的33种化合物30.001至30.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表31:
该表披露了具有化学式(Iaa)的33种化合物31.001至31.033,其中n是0,并且R2是OCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表32:
该表披露了具有化学式(Iaa)的33种化合物32.001至32.033,其中n是2,并且R2是OCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表33:
该表披露了具有化学式(Iaa)的33种化合物33.001至33.033,其中n是0,并且R2是SCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表34:
该表披露了具有化学式(Iaa)的33种化合物34.001至34.033,其中n是2,并且R2是SCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表35:
该表披露了具有化学式(Iaa)的33种化合物35.001至35.033,其中n是0,并且R2是SOCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表36:
该表披露了具有化学式(Iaa)的33种化合物36.001至36.033,其中n是2,并且R2是SOCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表37:
该表披露了具有化学式(Iaa)的33种化合物37.001至37.033,其中n是0,并且R2是SO2CF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表38:
该表披露了具有化学式(Iaa)的33种化合物38.001至38.033,其中n是2,并且R2是SO2CF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表39:
该表披露了具有化学式(Iaa)的33种化合物39.001至39.033,其中n是0,并且R2是Br,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表40:
该表披露了具有化学式(Iaa)的33种化合物40.001至40.033,其中n是2,并且R2是Br,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表41:
该表披露了具有化学式(Iaa)的33种化合物41.001至41.033,其中n是0,并且R2是CF2CH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表42:
该表披露了具有化学式(Iaa)的33种化合物42.001至42.033,其中n是2,并且R2是CF2CH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表43:
该表披露了具有化学式(Iaa)的33种化合物43.001至43.033,其中n是0,并且R2是OCF2CHFCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表44:
该表披露了具有化学式(Iaa)的33种化合物44.001至44.033,其中n是2,并且R2是OCF2CHFCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表45:
该表披露了具有化学式(Iaa)的33种化合物45.001至45.033,其中n是0,并且R2是OCF2CHFCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表46:
该表披露了具有化学式(Iaa)的33种化合物46.001至46.033,其中n是2,并且R2是OCF2CHFCF3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表47:
该表披露了具有化学式(Iaa)的33种化合物47.001至47.033,其中n是0,并且R2是C(CF3)2OCH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表48:
该表披露了具有化学式(Iaa)的33种化合物48.001至48.033,其中n是2,并且R2是C(CF3)2OCH3,R1是乙基,R4是CF3,并且Q如表X中X.001-X.033行所定义。
表49:该表披露了具有化学式(Iab)的33种化合物49.001至49.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物49.017具有以下结构:
表50:
该表披露了具有化学式(Iab)的33种化合物50.001至50.024,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表51:
该表披露了具有化学式(Iab)的33种化合物51.001至51.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表52:
该表披露了具有化学式(Iab)的33种化合物52.001至52.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表53:
该表披露了具有化学式(Iab)的33种化合物53.001至53.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表54:
该表披露了具有化学式(Iab)的33种化合物53.001至53.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表55:
该表披露了具有化学式(Iab)的33种化合物55.001至55.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表56:
该表披露了具有化学式(Iab)的33种化合物56.001至56.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表57:该表披露了具有化学式(Iac)的33种化合物57.001至57.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物57.021具有以下结构:
表58:
该表披露了具有化学式(Iac)的33种化合物58.001至58.024,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表59:
该表披露了具有化学式(Iac)的33种化合物59.001至59.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表60:
该表披露了具有化学式(Iac)的33种化合物60.001至60.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表61:
该表披露了具有化学式(Iac)的33种化合物61.001至61.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表62:
该表披露了具有化学式(Iac)的33种化合物62.001至62.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表63:
该表披露了具有化学式(Iac)的33种化合物63.001至63.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表64:
该表披露了具有化学式(Iac)的33种化合物64.001至64.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表65:该表披露了具有化学式(Iad)的33种化合物65.001至65.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物65.016具有以下结构:
表66:
该表披露了具有化学式(Iad)的33种化合物66.001至66.024,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表67:
该表披露了具有化学式(Iad)的33种化合物67.001至67.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表68:
该表披露了具有化学式(Iad)的33种化合物68.001至68.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表69:
该表披露了具有化学式(Iad)的33种化合物69.001至69.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表70:
该表披露了具有化学式(Iad)的33种化合物70.001至70.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表71:
该表披露了具有化学式(Iad)的33种化合物71.001至71.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表72:
该表披露了具有化学式(Iad)的33种化合物72.001至72.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表73:该表披露了具有化学式(Iae)的33种化合物73.001至73.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物73.024具有以下结构:
表74:
该表披露了具有化学式(Iae)的33种化合物74.001至74.024,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表75:
该表披露了具有化学式(Iae)的33种化合物75.001至75.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表76:
该表披露了具有化学式(Iae)的33种化合物76.001至76.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表77:
该表披露了具有化学式(Iae)的33种化合物77.001至77.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表78:
该表披露了具有化学式(Iae)的33种化合物78.001至78.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表79:
该表披露了具有化学式(Iae)的33种化合物79.001至79.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表80:
该表披露了具有化学式(Iae)的33种化合物80.001至80.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表81:该表披露了具有化学式(Iaf)的33种化合物81.001至81.033:
其中n是0,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。例如,化合物81.007具有以下结构:
表82:
该表披露了具有化学式(Iaf)的33种化合物82.001至82.033,其中n是2,并且R2是CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表83:
该表披露了具有化学式(Iaf)的33种化合物83.001至83.033,其中n是0,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表84:
该表披露了具有化学式(Iaf)的33种化合物84.001至84.033,其中n是2,并且R2是CF2CF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表85:
该表披露了具有化学式(Iaf)的33种化合物85.001至85.033,其中n是0,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表86:
该表披露了具有化学式(Iaf)的33种化合物86.001至86.033,其中n是2,并且R2是CF(CF3)2,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表87:
该表披露了具有化学式(Iaf)的33种化合物87.001至87.033,其中n是0,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
表88:
该表披露了具有化学式(Iaf)的33种化合物88.001至88.033,其中n是2,并且R2是SCF3,R1是乙基,R4是氢,并且Q如表X中X.001-X.033行所定义。
根据本发明的具有化学式I的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有非常有利的杀生物谱并且是温血物种、鱼以及植物良好耐受的。根据本发明的活性成分作用于正常敏感的以及还有抗药的动物有害生物(如昆虫或蜱螨目的代表)的所有的或个别的发育阶段。根据本发明的活性成分的杀昆虫或杀螨活性可以本身直接显示,亦即或者立即或者仅在过去一些时间之后(例如在蜕皮期间)发生破坏有害生物;或间接显示,例如降低产卵和/或孵化率。
上述动物有害生物的实例是:
来自蜱螨目,例如,
下毛瘿螨属(Acalitus spp.)、针刺瘿螨属(Aculus spp)、窄瘿螨属(Acaricalusspp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苔螨属(Bryobia spp)、上三节瘿螨属(Calipitrimerus spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、表皮螨属(Dermatophagoides spp)、始叶螨属(Eotetranychus spp)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、小爪螨属(Olygonychus spp)、钝缘蜱属(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属(Panonychusspp.)、桔芸锈螨(Phyllocoptruta oleivora)、植食螨(Phytonemus spp.)、跗线螨属(Polyphagotarsonemus spp)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、狭跗线螨属(Steneotarsonemus spp)、跗线属(Tarsonemus spp.)以及叶螨属(Tetranychus spp.);
来自虱目,例如,
血虱属、长颚虱属、人虱属、天疱疮属以及木虱属;
来自鞘翅目,例如,
缺隆叩甲属(Agriotes spp.)、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟(Anomala orientalis)、花象属(Anthonomus spp.)、蜉金龟属(Aphodius spp)、玉米拟花萤(Astylus atromaculatus)、Ataenius属、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnema tibialis)、萤叶甲属(Cerotoma spp)、单叶叩甲属(Conoderus spp)、根颈象属(Cosmopolites spp.)、绿金龟(Cotinisnitida)、象虫属(Curculio spp.)、圆头犀金龟属(Cyclocephala spp)、圆头犀金龟属(Dermestes spp.)、根萤叶甲属(Diabroticaspp.)、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属(Epilachna spp.)、Eremnus属、黑异爪蔗金龟(Heteronychus arator)、咖啡果小蠹(Hypothenemus hampei)、Lagriavilosa、马铃薯甲虫(Leptinotarsa decemLineata)、稻水象属(Lissorhoptrus spp.)、Liogenys属、Maecolaspis属、栗色绒金龟(Maladera castanea)、美洲叶甲亚种(Megascelis spp)、油菜花露尾甲(Melighetes aeneus)、金龟属(Melolontha spp.)、Myochrous armatus、锯谷盗属(Orycaephilus spp.)、耳喙象属(Otiorhynchus spp.)、鳃角金龟属(Phyllophaga spp)、斑象属(Phlyctinus spp.)、丽金龟属(Popillia spp.)、油菜跳甲属(Psylliodes spp.)、Rhyssomatus aubtilis、劫根蠹属(Rhizopertha spp.)、金龟子科(Scarabeidae)、米象属(Sitophilus spp.)、麦蛾属(Sitotroga spp.)、伪切根虫属(Somaticus spp)、Sphenophorus属、大豆茎象(Sternechus subsignatus)、拟步行虫属(Tenebrio spp.)、拟谷盗属(Tribolium spp.)以及斑皮蠹属(Trogoderma spp.);
来自双翅目,例如,
伊蚊属(Aedes spp.)、疟蚊属(Anopheles spp)、高梁芒蝇(Antherigonasoccata.)、橄榄果实蝇(Bactrocea oleae)、花园毛蚊(Bibio hortulanus)、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇(Calliphora erythrocephala)、小条实蝇属(Ceratitisspp.)、金蝇属(Chrysomyia spp.)、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、寡鬃实蝇属(Dacus spp.)、地种蝇属(Delia spp)、黑腹果蝇(Drosophilamelanogaster)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilus spp.)、Geomyza tripunctata、舌蝇属(Glossinaspp.)、皮蝇属(Hypoderma spp.)、虱蝇属(Hyppobosca spp.)、斑潜蝇属(Liriomyzaspp.)、绿蝇属(Lucilia spp.)、潜蝇属(Melanagromyza spp.)、家蝇属(Musca spp.)、狂蝇属(Oestrus spp.)、瘿蚊属(Orseolia spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbia spp.)、绕实蝇属(Rhagoletis spp)、Riveliaquadrifasciata、Scatella属、蕈蚊属(Sciara spp.)、刺蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、绦虫属(Tannia spp.)以及大蚊属(Tipula spp.);
来自半翅目,例如,
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypelta nitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属、Edessa spp.、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horcias nobilellus)、稻缘蝽属、草盲蝽属、热带硕蚧属、卷心菜斑色蝽(Murgantiahistrionic)、Neomegalotomus spp.、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysius simulans)、Oebalus insularis、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、Scaptocoris castanea、黑蝽属(Scotinophara spp.)、Thyanta spp.、锥鼻虫属、木薯网蝽(Vatiga illudens);
无网长管蚜属、Adalges spp.、Agalliana ensigera、Agonoscena targionii、粉虱属(Aleurodicus spp.)、Aleurocanthus spp.、甘蔗穴粉虱、软毛粉虱(Aleurothrixusfloccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarasca biguttula)、Amritodusatkinson、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、Bactericeracockerelli、小粉虱属、Brachycaudus spp.、甘蓝蚜、喀木虱属、双尾蚜(Cavariellaaegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、Cicadella spp.、大白叶蝉(Cofanaspectra)、隐瘤蚜属、Cicadulina spp.、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspisbrimblecombei)、菜缢管蚜、Hyalopterus spp.、超瘤蚜种、檬果绿叶蝉(Idioscopusclypealis)、Jacobiasca lybica、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphiserysimi)、Lyogenys maidis、长管蚜属、Mahanarva spp.、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、Odonaspis ruthae、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinaria aethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、Spissistilus festinus、条斑飞虱(TarophagusProserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、Zygina flammigera、Zyginidia scutellaris;
来自膜翅目,例如,
顶切叶蚁属(Acromyrmex)、三节叶蜂属(Arge spp.)、布切叶白蚁属(Atta spp.)、茎叶蜂属(Cephus spp.)、松叶蜂属(Diprion spp.)、锯角叶蜂科(Diprionidae)、松叶蜂(Gilpinia polytoma)、梨实蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小黄家蚁(Monomorium pharaonis)、新松叶蜂属(Neodiprion spp.)、农蚁属(Pogonomyrmex spp)、Slenopsis invicta、水蚁属(Solenopsis spp.)以及胡蜂属(Vespa spp.);
来自等翅目,例如,
家白蚁属、白蚁(Corniternes cumulans)、楹白蚁属、大白蚁属、澳白蚁属、小白蚁属、散白蚁属;热带火蚁
来自鳞翅目,例如,
长翅卷蛾属、褐带卷蛾属、透翅蛾属、地夜蛾属、棉叶虫、Amylois spp.、黎豆夜蛾、黄卷蛾属、银蛾属(Argyresthia spp.)、带卷蛾属、丫纹夜蛾属、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃蛀果蛾、禾草螟属、卷叶蛾属、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾、卷叶螟属、云卷蛾属、纹卷蛾属、鞘蛾属、磷翅目粉蝶、Cosmophila flava、草螟属、大菜螟、苹果异形小卷蛾、黄杨木蛾、小卷蛾属、黄杨绢野螟、杆草螟属、苏丹棉铃虫、金刚钻属、非洲茎螟、粉螟属、叶小卷蛾属(Epinotia spp)、细斑灯蛾、Etiella zinckinella、花小卷蛾属、环针单纹蛾、黄毒蛾属、切根虫属、Feltia jaculiferia、Grapholita spp.、绿青虫蛾、实夜蛾属、菜螟、切叶野螟属(Herpetogramma spp)、美国白蛾、番茄蠹蛾、Lasmopalpuslignosellus、旋纹潜叶蛾、潜叶细蛾属、葡萄花翅小卷蛾、Loxostege bifidalis、毒蛾属、潜蛾属、幕枯叶蛾属、甘蓝夜蛾、烟草天蛾、Mythimna spp、夜蛾属、秋尺蛾属、Orniodesindica、欧洲玉米螟、超小卷蛾属、褐卷蛾属、小眼夜蛾、蛀茎夜蛾、Pectinophora gossypi-ela、咖啡潜叶蛾、一星黏虫、马铃薯麦蛾、菜粉蝶、粉蝶属、小菜蛾、芽蛾属、尺叶蛾属、薄荷灰夜蛾、西方豆地香(Richia albicosta)、白禾螟属(Scirpophaga spp.)、蛀茎夜蛾属、长须卷蛾属、灰翅夜蛾属、棉大卷叶螟、兴透翅蛾属、异舟蛾属、卷叶蛾属、粉纹夜蛾、番茄斑潜蝇、以及巢蛾属;
来自食毛目,例如,
畜虱属和啮毛虱属;
来自直翅目,例如,
蠊属、小蠊属、蝼蛄属、马德拉蜚蠊、飞蝗属、北痣蟋蟀(Neocurtillahexadactyla)、大蠊属、痣蟋蟀属(Scapteriscus spp.)、以及沙漠蝗属;
来自啮虫目,例如,
虱啮属(Liposcelis spp.);
来自蚤目,例如,
角叶蚤属、栉头蚤属和印鼠客蚤;
来自缨翅目,例如,
Calliothrips phaseoli、花蓟马属、阳蓟马属、褐带蓟马属、单亲蓟马属(Parthenothrips spp.)、非洲桔硬蓟马(Scirtothrips aurantii)、大豆蓟马(Sericothrips variabilis)、带蓟马属、蓟马属;
来自缨尾目,例如衣鱼(Lepisma saccharina)。
根据本发明的活性成分可用于控制、也就是遏制或破坏上述类型的有害生物,这些有害生物特别出现在植物上,尤其是在农业中、在园艺中以及在林业中的有用的植物和观赏植物上,或者在这些植物的器官上,例如果实、花、叶、茎、块茎或根,并且在一些情况下,甚至在一个随后的时间点形成的植物器官仍保持受保护抵抗这些有害生物。
适宜的目标作物具体是,谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如梨果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、荼、胡椒、葡萄藤、蛇麻草、车前草科以及乳胶植物。
本发明的组合物和/或方法还可以用在任何观赏植物和/或蔬菜作物(包括花、灌木、阔叶树和常绿植物)上。
例如,本发明可以用在任何以下观赏植物物种上:藿香蓟属、假面花属(Alonsoaspp.)、银莲花属、南非葵、春黄菊属、金鱼草属、紫菀属、秋海棠属(例如丽格海棠、四季秋海棠、球根秋海棠(B.tubéreux))、叶子花属、雁河菊属(Brachycome spp.)、芸苔属(观赏植物)、蒲包草属、辣椒、长春花、美人蕉属、矢车菊属、菊属、瓜叶菊属(银叶菊)、金鸡菊属、青锁龙(Crassula coccinea)、火红萼距花(Cuphea ignea)、大丽花属、翠雀属、荷包牡丹、彩虹菊属(Dorotheantus spp.)、洋桔梗、连翘属、倒挂金钟属、鼠曲草老颧草(Geraniumgnaphalium)、大丁草属、千日红、天芥菜属、向日葵属、木槿属、绣球花属、绣球属、嫣红蔓、凤仙花属(非洲凤仙花)、血苋属(Iresines spp.)、伽蓝菜属、马缨丹、三月花葵、狮耳花、百合属、日中花属、沟酸浆属、美国薄荷属、龙面花属、万寿菊属、石竹属(康乃馨)、美人蕉属、酢浆草属、雏菊属、天竺葵属(盾叶天竺葵、马蹄纹天竺葵)、堇菜属(三色堇)、碧冬茄属、草夹竹桃属、香茶菜属(Plecthranthus spp.)、一品红属、爬山虎属(五叶爬山虎、爬山虎)、报春花属、毛茛属、杜鹃花属、蔷薇属(玫瑰)、黄雏菊属、非洲堇属、鼠尾草属、紫扇花(Scaevola aemola)、蛾蝶花(Schizanthus wisetonensis)、景天属、茄属、苏非尼亚矮牵牛属(Surfinia spp.)、万寿菊属、烟草属、马鞭草属、百日草属以及其他花坛植物。
例如,本发明可以用在任何以下蔬菜物种上:葱属(大蒜、洋葱、火葱(A.oschaninii)、韭葱、小葱、大葱)、有喙欧芹、旱芹、芦笋、甜菜、芸苔属(甘蓝、大白菜、芜菁)、辣椒、鹰嘴豆、苦苣、菊苣属(菊苣、苦苣)、西瓜、黄瓜属(黄瓜、甜瓜)、南瓜属(西葫芦、印度南瓜)、菜蓟属(朝鲜蓟、刺苞菜蓟)、胡萝卜、茴香、金丝桃属、莴苣、番茄属(番茄、樱桃番茄)、薄荷属、罗勒、香芹、菜豆属(菜豆、荷包豆)、豌豆、萝卜、食用大黄、迷迭香属、鼠尾草属、黑婆罗门参、茄子、菠菜、新缬草属(莴苣缬草、V.eriocarpa)以及蚕豆。
优选的观赏植物物种包括非洲堇、秋海棠属、大丽花属、大丁草属、绣球属、马鞭草属、蔷薇属、伽蓝菜属、一品红属、紫菀属、矢车菊属、金鸡菊属、翠雀属、美国薄荷属、草夹竹桃属、黄雏菊属、景天属、碧冬茄属、堇菜属、凤仙花属、老鹳草属、菊属、毛茛属、倒挂金钟属、鼠尾草属、绣球花属、迷迭香、鼠尾草、圣约翰草、薄荷、甜椒、番茄和黄瓜。
根据本发明的活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
在另一个方面,本发明还可以涉及控制由植物寄生的线虫(内寄生的-、半内寄生的-以及外寄生的线虫)对植物或其部分引起损害的方法,尤其是以下植物寄生的线虫,如根结线虫(root knot nematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogyne arenaria)以及其他根结线虫属种类(Meloidogyne species);孢囊形成线虫(cyst-forming nematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属种类(Globodera species);禾谷孢囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heterodera trifolii)、以及其他异皮线虫属种类(Heterodera species);种瘿线虫(Seed gall nematodes)、粒线虫属种类(Anguina species);茎及叶面线虫(Stem andfoliar nematodes)、滑刃线虫属种类(Aphelenchoides species);刺毛线虫(Stingnematodes)、长尾刺线虫(Belonolaimus longicaudatus)以及其他刺线虫属种类;松树线虫(Pine nematodes)、松材线虫(Bursaphelenchus xylophilus)以及其他伞滑刃属种类(Bursaphelenchus species);环形线虫(Ring nematodes)、环线虫属种类(Criconemaspecies)、小环线虫属种类(Criconemella species)、轮线虫属种类(Criconemoidesspecies)、中环线虫属种类(Mesocriconema species);茎及鳞球茎线虫(Stem and bulbnematodes)、腐烂茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchusdipsaci)以及其他茎线虫属种类(Ditylenchus species);锥线虫(Awl nematodes)、锥线虫属种类(Dolichodorus species);螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属种类(Helicotylenchusspecies);鞘及鞘形线虫(Sheath and sheathoid nematodes)、鞘线虫属种类(Hemicycliophora species)以及半轮线虫属种类(Hemicriconemoides species);潜根线虫属种类(Hirshmanniella species);支线虫(Lance nematodes)、冠线虫属种类(Hoploaimus species);假根结线虫(false rootknot nematodes)、珍珠线虫属种类(Nacobbus species);针状线虫(Needle nematodes)、横带长针线虫(Longidoruselongatus)以及其他长针线虫属种类(Longidorus species);大头针线虫(Pinnematodes)、短体线虫属种类(Pratylenchus species);腐线虫(Lesion nematodes)、花斑短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchus penetrans)、弯曲短体线虫(Pratylenchus curvitatus)、古氏短体线虫(Pratylenchus goodeyi)以及其他短体线虫属种类(Pratylenchus species);柑桔穿孔线虫(Burrowingnematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属种类(Radopholus species);肾形线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchus robustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属种类(Rotylenchus species);盾线虫属种类(Scutellonema species);短粗根线虫(Stubby root nematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属种类(Trichodorus species)、拟毛刺线虫属种类(Paratrichodorus species);矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属种类(Tylenchorhynchus species);柑桔线虫(Citrus nematodes)、穿刺线虫属种类(Tylenchulus species);短剑线虫(Dagger nematodes)、剑线虫属种类(Xiphinemaspecies);以及其他植物寄生的线虫种类,如亚粒线虫属(Subanguina spp.)、Hypsoperine属、大刺环线虫属(Macroposthonia spp.)、Melinius属、刻点胞囊属(Punctodera spp.)、以及五沟线虫属(Quinisulcius spp.)。
本发明的化合物还具有针对软体动物的活性。这些软体动物的实例包括例如苹果螺科;阿勇蛞蝓属(Arion)(灰黑阿勇蛞蝓(A.ater)、环斑阿勇蛞蝓(A.circumscriptus)、庭院阿勇蛞蝓(A.hortensis)、红棕阿勇蛞蝓(A.rufus));巴蜗牛科(灌木巴蜗牛(Bradybaenafruticum));蜗牛属(庭院蜗牛(C.hortensis)、森林蜗牛(C.Nemoralis));ochlodina;灰蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、田灰蛞蝓(D.laeve)、庭园灰蛞蝓(D.reticulatum));圆盘螺属(Discus)(D.rotundatus);Euomphalia;土蜗属(Galba)(截形土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科Helicigona arbustorum);Helicodiscus;大蜗牛属(Helix)(开放大蜗牛(H.aperta));蛞蝓属(Limax)(灰黑蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus)、边缘蛞蝓(L.marginatus)、大蛞蝓(L.maximus)、柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(M.gagates、M.marginatus、M.sowerbyi);钻螺属(Opeas);瓶螺属(Pomacea)(P.canaticulata);瓦娄蜗牛属(Vallonia)和Zanitoides。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素如已知,例如来自产毒素的细菌,尤其是芽孢杆菌属的那些。
可以通过此类转基因植物表达的毒素包括例如杀昆虫蛋白,例如来自于蜡样芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白;或来自于苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀虫蛋白,例如光杆状菌属或致病杆菌属,如发光光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素;植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、HMG-COA-还原酶,离子通道阻断剂,如钠通道或钙通道阻断剂,保幼激素酯酶,利尿激素受体、茋合酶、联苄合酶、几丁质酶和葡聚糖酶。
在本发明背景下,δ-内毒素例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同区域的新组合重组产生的(参见,例如WO 02/15701)。截短的毒素例如截短的Cry1Ab是已知的。在经修饰毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这样的氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的实例披露于例如EP-A-0 374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法对于本领域技术人员是已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979以及WO 90/13651中已知。
包括在转基因植物中的毒素使得植物对有害昆虫有耐受性。这样的昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
包含一个或多个编码杀虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。此类植物的实例为:(玉米品种,表达Cry1Ab毒素);YieldGard(玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab以及Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac和Cry2Ab毒素);(棉花品种,表达Vip3A和Cry1Ab毒素);(马铃薯品种,表达Cry3A毒素); GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状)以及
这样的转基因作物的其他实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31 790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵的耐受性。
2.Bt176玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。这样的转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传改性的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自孟山都公司(Monsanto Europe S.A.),270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK 603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的作物,这些抗病原物质是例如像所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225)。这样的抗病原物质和能够合成这样的抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 95/33818和EP-A-0 353 191是已知的。生产这样的转基因植物的方法对于本领域的普通技术人员而言通常是已知的并且描述于例如以上提及的公开物中。
作物也可以经修饰以增加对真菌(例如镰孢霉属、炭疽病或疫霉属)、细菌(例如假单胞菌属)或病毒(例如马铃薯卷叶病毒、番茄斑萎病毒、黄瓜花叶病毒)病原体的抗性。
作物还包括那些对线虫(如大豆异皮线虫)具有增加的抗性的作物。
具有对非生物性胁迫的耐受性的作物包括那些例如通过NF-YB或本领域中已知的其他蛋白质的表达对干旱、高盐、高温、寒冷、霜或光辐射具有增加的耐受性的作物。
可以由此类转基因植物表达的抗病原物质包括,例如,离子通道阻断剂(例如钠和钙通道阻断剂,像病毒的KP1、KP4或KP6毒素);芪合酶;联苄合酶;几丁质酶;葡聚糖酶;所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225);由微生物产生的抗病原物质,例如涉及植物病原体防御的肽抗生素或杂环类抗生素(参见例如WO 95/33818)或蛋白质或多肽因子(所谓的“植物疾病抗性基因”,如描述于WO 03/000906中的)。
根据本发明的组合物的其他使用范围是保护所储存的货物和储藏室以及保护原材料,如木材、纺织品、地板或建筑物,以及在卫生领域中,尤其是保护人类、家畜以及多产的牲畜免遭所提及类型的有害生物。
本发明还提供了用于控制有害生物(如蚊和其他的疾病媒介物;同样参见http://www.who.int/malaria/vector_control/irs/en/)的方法。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向目标有害生物、它们的场所或表面或基质施用本发明的组合物。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,预期了将这样的组合物施用于基质,如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)。
在一个实施例中,用于控制这样的有害生物的方法包括向目标有害生物、它们的场所或表面或基质施用杀有害生物有效量的本发明的组合物,以便于在该表面或基质上提供有效的滞留的杀有害生物活性。这样的施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,预期了施用这样的组合物以用于在基质上的有害生物的滞留的控制,该基质是如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)的织物材料。
待处理的基质(包括无纺物、织物或网织品)可以由天然纤维,如棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或者合成纤维,如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO 2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO2007/090739。
根据本发明的组合物的其他使用范围是针对所有观赏树木连同所有种类的果树和坚果树的树木注射/树干处理领域。
在树木注射/树干处理领域中,根据本发明的这些化合物特别适合于对抗来自上述的鳞翅目和来自鞘翅目的钻木昆虫,尤其是对抗下表A和B中列出的钻木虫:
表A.具有经济重要性的外来钻木虫的实例。
表B.具有经济重要性的本地钻木虫的实例。
本发明也可以用于控制任何可以存在于草坪草中的昆虫有害生物,包括例如甲虫、毛虫、火蚁、地面珍珠(ground pearl)、千足虫、潮虫、螨虫、蝼蛄、介壳虫、粉蚧蜱、沫蝉、南方麦小蝽以及蛴螬。本发明可以用于控制处于其生命周期的各个阶段的昆虫有害生物,包括卵、幼虫、若虫和成虫。
具体而言,本发明可以用于控制取食草坪草的根部的昆虫有害生物,这些昆虫有害生物包括蛴螬(如圆头犀金龟属(Cyclocephala spp.)(例如蒙面金龟子,C.lurida)、Rhizotrogus属(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属(Cotinus spp.)(例如绿六月甲虫(Green June beetle),C.nitida)、弧丽金龟属(Popillia spp.)(例如日本甲虫,龟纹瓢虫(P.japonica))、鳃角金龟属(Phyllophaga spp.)(例如五月/六月甲虫)、Ataenius属(例如草坪草黑金龟(Black turfgrass ataenius),A.spretulus)、绒毛金龟属(Maladera spp.)(例如亚洲花园甲虫(Asiatic garden beetle),M.castanea)以及Tomarus属),地面珍珠(硕蚧属(Margarodes spp.)),蝼蛄(褐黄色的、南方的、以及短翅的;痣蟋蟀属(Scapteriscus spp.),非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly),大蚊属(Tipula spp.))。
本发明还可以用于控制茅草住宅的草坪草的昆虫有害生物,这些昆虫有害生物包括粘虫(如秋夜蛾(fall armyworm)草地贪夜蛾(Spodoptera frugiperda),和常见夜蛾一星黏虫(Pseudaletia unipuncta))、切根虫,象鼻虫(尖隐喙象属(Sphenophorus spp.),如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属(Crambus spp.)和热带草地螟,Herpetogramma phaeopteralis)。
本发明还可以用于控制在地上生活并取食草坪草叶子的草坪草中的昆虫有害生物,这些昆虫有害生物包括麦小蝽(如南方麦小蝽,南方杆长蝽(Blissus insularis))、狗牙根螨(Bermudagrass mite)(Eriophyes cynodoniensis)、盖氏虎尾草粉蚧(草竹粉蚧(Antonina graminis))、两线沫蝉(Propsapia bicincta)、叶蝉、切根虫(夜蛾科)、以及麦二叉蚜。
本发明还可以用于控制草坪草中的其他有害生物,如在草坪中创建蚁巢的外引红火蚁(红火蚁(Solenopsis invicta))。
在卫生领域中,根据本发明的组合物是有效地对抗外寄生虫如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和蚤的。
这样的寄生虫的实例是:
虱目:血虱属、长颚虱属、人虱属和阴虱属、盲虱属。
食毛目:毛羽虱属、短角鸟虱属、鸭虱属、牛羽虱属、Werneckiella属、Lepikentron属、畜虱属、啮毛虱属以及猫羽虱属。
双翅目及长角亚目和短角亚目,例如伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、罗蛉属、库蠓属、斑虻属、驼背虻属、黄虻属、虻属、麻虻属、Philipomyia属、蜂虱蝇属、家蝇属、齿股蝇属、螫蝇属、黑角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、污蝇属、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、羊虱蝇属和蜱蝇属。
蚤目,例如蚤属、栉头蚤属、客蚤属、角叶蚤属。
异翅目,例如臭虫属、锥蝽属、红猎蝽属、锥蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国小蠊以及夏柏拉蟑螂属。
蜱螨亚纲(螨科)和后气门目和中气门目,例如锐缘蜱属、钝缘蜱属、耳蜱属、硬蜱属、钝眼蜱属、牛蜱属、革蜱属、血蜱属、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸刺螨属和瓦螨属。
轴螨目(前气门亚目)和粉螨目(无气门亚目),例如蜂盾螨属、姬螯属、禽螯螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、痒螨属、皮螨属、耳疥螨属、疥螨属、耳螨属、鸟疥螨属、胞螨属以及鸡雏螨属。
根据本发明的组合物还适用于保护材料如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等免受昆虫侵染。
根据本发明的组合物可以用于例如对抗以下有害生物:甲虫,如北美家天牛、长毛天牛、家具窃蠹、红毛窃蠹、梳角细脉窃蠹、石斛、松芽枝窃蠹、松产品窃蠹、褐粉蠹、非洲粉蠹、南方粉蠹、栎粉蠹、柔毛粉蠹、胸粉蠹、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、树长蠹、棕异翅长蠹、双棘长蠹属与竹长蠹;以及膜翅类昆虫,如蓝黑树蜂、云杉大树蜂、泰加大树蜂与大树蜂;以及白蚁,如欧洲木白蚁、麻头堆砂白蚁、印巴结构木异白蚁、黄胸散白蚁、桑特散白蚁、散白蚁、达尔文澳白蚁、内华达古白蚁与家白蚁;以及蛀虫,如衣鱼。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们通常以多种方式使用配制佐剂(如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从关于杀有害生物剂的FAO和WHO标准的发展和使用的手册(Manual on Developmentand Use of FAO and WHO Specifications for Pesticides),联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者可以使用前稀释再使用。可以利用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来稀释。
可以通过例如将活性成分与配制辅助剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳液形式的组合物。这些活性成分还可以与其他辅助剂(例如精细分散固体、矿物油、植物或动物的油、改性的植物或动物的油、有机溶剂、水、表面活性物质或它们的组合)来一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有活性成分。这使活性成分能以受控的量值(例如,缓慢释放)释放到环境中。微胶囊通常具有从0.1微米至500微米的直径。它们含有的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于合适溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶、纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸盐、或本领域的普通技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合于制备根据本发明的这些组合物的配制佐剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯的乙酸、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇乙醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是,例如滑石、二氧化钛、叶蜡石粘土、硅石、凹凸棒石粘土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木素和类似的物质。
许多表面活性物质可以有利地用在固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性物质包括例如烷基硫酸酯的盐,如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如乙氧基化壬基苯酚;醇/氧化烯加成产物,如乙氧基化十三烷醇;皂,如硬脂酸钠;烷基萘磺酸酯的盐,如二丁基萘磺酸钠;磺基丁二酸盐的二烷基酯,如二(2-乙基己基)磺基丁二酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季铵,如氯化十二烷基三甲基铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单-和二-烷酯的盐;以及还有例如在麦卡琴清洁剂和乳化剂年鉴(McCutcheon’s Detergents and Emulsifiers Annual),MC出版公司(MC PublishingCorp.),里奇伍德(Ridgewood),新泽西州(1981)中所述的其他物质。
可以用于杀有害生物配制品的其他佐剂包括结晶作用抑制剂、粘度改性剂、悬浮剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或改变pH的物质与缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体与固体肥料。
根据本发明的组合物可以包括添加剂,该添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明的组合物中的油添加剂的量通常是该待施用的混合物的0.01%到10%。例如,可以在喷雾混合物已经制备以后将该油添加剂以所希望的浓度加入喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)的甲基酯。许多油衍生物获知于除草剂佐剂纲要(Compendium of HerbicideAdjuvants),第10版,南伊利诺伊大学,2010。
这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0至25%的表面活性物质。而商用产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用量在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、待控制的有害生物、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。一般来讲,可以将化合物以从1l/ha至2000l/ha,尤其是从10l/ha到1000l/ha的比率施用。
优选的配制品可以具有以下成分(重量%):
可乳化浓缩剂:
活性成分: 1%至95%,优选60%至90%
表面活性剂: 1%至30%,优选5%至20%
液体载体: 1%至80%,优选1%至35%
尘剂:
活性成分: 0.1%至10%,优选0.1%至5%
固体载体: 99.9%至90%,优选99.9%至99%
悬浮液浓缩剂:
活性成分: 5%至75%,优选10%至50%
水: 94%至24%,优选88%至30%
表面活性剂: 1%至40%,优选2%至30%
可湿性粉剂:
活性成分: 0.5%至90%,优选1%至80%
表面活性剂: 0.5%至20%,优选1%至15%
固体载体: 5%至95%,优选15%至90%
颗粒剂:
活性成分: 0.1%至30%,优选0.1%至15%
固体载体: 99.5%至70%,优选97%至85%
以下实例进一步展示了(但不限制)本发明。
<u>可湿性粉剂</u> | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木质素磺酸钠 | 5% | 5% | - |
月桂基硫酸钠 | 3% | - | 5% |
二异丁基萘磺酸钠 | - | 6% | 10% |
苯酚聚乙二醇醚(7-8mol环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将该组合与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而获得了可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该组合与佐剂充分混合并且将该混合物在适合的研磨机中充分研磨,从而获得可以直接用于种子处理的粉剂。
<u>可乳化浓缩剂</u> | |
活性成分 | 10% |
辛基酚聚乙二醇醚(4-5mol环氧乙烷) | 3% |
十二烷基苯磺酸钙 | 3% |
蓖麻油聚乙二醇醚(35mol环氧乙烷) | 4% |
环己酮 | 30% |
二甲苯混合物 | 50% |
在植物保护中可以使用的具有任何所要求稀释度的乳液可以通过用水稀释从这种浓缩物中获得。
<u>尘剂</u> | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填充剂 | - | - | 96% |
通过将该组合与载体混合并且将混合物在适当的研磨机中研磨获得立即可用的尘剂。此类粉剂还可以用于种子的干法敷料。
<u>挤出机颗粒剂</u> | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将该组合与这些佐剂混合并且研磨,并且将混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
<u>包衣的颗粒剂</u> | |
活性成分 | 8% |
聚乙二醇(分子量200) | 3% |
高岭土 | 89% |
将这种精细研磨的组合在混合器中均匀地施用到用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩剂
活性成分 | 40% |
丙二醇 | 10% |
壬基苯酚聚乙二醇醚(15mol环氧乙烷) | 6% |
木质素磺酸钠 | 10% |
羧甲基纤维素 | 1% |
硅油(处于在水中75%的乳液的形式) | 1% |
水 | 32% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩剂,可以使用水稀释从该浓缩物获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
种子处理用的可流动性浓缩剂
活性成分 | 40% |
丙二醇 | 5% |
共聚物丁醇PO/EO | 2% |
三苯乙烯酚,具有10-20摩尔EO | 2% |
1,2-苯并异噻唑啉-3-酮(处于在水中20%的溶液形式) | 0.5% |
单偶氮颜料钙盐 | 5% |
硅油(呈在水中75%乳液的形式) | 0.2% |
水 | 45.3% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩物,可以使用水稀释从该浓缩物获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
缓释的胶囊悬浮剂
将28份的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的颗粒尺寸。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将该混合物搅拌直至聚合反应完成。将获得的胶囊悬浮剂通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮剂配制品包含28%的活性成分。该介质胶囊的直径是8微米-15微米。将所得配制品作为适用于此目的的装置中的水性悬浮液施用到种子上。
配制品类型包括乳液浓缩剂(EC)、悬浮液浓缩物(SC)、悬乳剂(SE)、胶囊悬浮剂(CS)、水可分散性颗粒剂(WG)、可乳化性颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散体(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩剂(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩剂(DC)、可湿性粉剂(WP)、可溶性颗粒剂(SG)或与农业上可接受的佐剂组合的任何技术上可行的配制品。
制备实例:
“Mpt.”是指以℃计的熔点。自由基表示甲基基团。1H NMR测量值在Brucker400MHz分光计上记录,化学位移相对于TMS标准品以ppm给出。光谱在如指定的氘代溶剂中测量。
LCMS方法:
方法1:
在来自沃特斯(Waters)的质谱仪(SQD、SQDII或ZQ单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热管柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8mm,30x2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:10%-100%B,在1.2min内;流量(mL/min)0.85
实例H1:2-[3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]-2-吡啶基]-3-甲基-6-
(三氟甲基)咪唑并[4,5-c]吡啶(化合物P3,表P):
步骤A:N-[4-氨基-6-(三氟甲基)-3-吡啶基]氨基甲酸叔丁基酯
向6-(三氟甲基)吡啶-3,4-二胺(3.14g,17.73mmol,如US 7,767,687中所描述制备的)于四氢呋喃(50ml)中的溶液中添加叔丁氧基羰基叔丁基碳酸酯(4.64g,21.27mmol)并且将混合物在50℃下进行搅拌。8小时之后,再添加1.1g(5.0mmol)的叔丁氧基羰基叔丁基碳酸酯,并且在50℃下再继续搅拌4小时。然后将反应混合物在真空中浓缩,并且将棕色残余物悬浮于二氯甲烷中,过滤并在真空中干燥,以给出呈白色晶体的标题化合物。LCMS(方法A):保留时间:0.79min;278(M+H)。
步骤B:叔N-[4-氨基-6-(三氟甲基)-3-吡啶基]-N-甲基-氨基甲酸丁基酯
在20℃-25℃下,经20min的时间段向氢化钠(0.648g,14.85mmol)于30ml N,N-二甲基甲酰胺中的搅拌悬浮液中滴加溶解于20ml N,N-二甲基甲酰胺中的N-[4-氨基-6-(三氟甲基)-3-吡啶基]氨基甲酸叔丁基酯(3.92g,14.14mmol)。在环境温度下搅拌15min后,添加碘甲烷(2.21g,15.55mmol)。在环境温度下30min之后,将混合物倒在200ml水上,用乙酸乙酯萃取两次,并且将合并的有机级分依次用水和盐水洗涤,经Na2SO4干燥并在真空中浓缩。将粗产物从乙酸乙酯/庚烷中重结晶,以给出呈白色晶体的标题化合物(3.18g)。LCMS(方法A):保留时间:0.85min;292(M+H)。
步骤C:N3-甲基-6-(三氟甲基)吡啶-3,4-二胺
向N-[4-氨基-6-(三氟甲基)-3-吡啶基]-N-甲基-氨基甲酸叔丁基酯(3.53g,12.119mmol)于二噁烷中的澄清无色溶液中添加氯化氢(18mL的在水中的2M溶液,36.36mmol),并将该混合物加热至回流。气体逸出停止之后,将反应混合物冷却至室温,并用固体碳酸氢钠(3.1g,36.9mmol)处理。将浆液用水稀释并用乙酸乙酯萃取两次。将合并的有机层依次用水和盐水洗涤,经Na2SO4干燥并在真空中浓缩,以给出2.25g呈无色晶体的标题化合物,Mpt138℃-140℃。LCMS(方法A):保留时间0.24min,192(M+H)。
可替代地,可以通过以下程序获得N3-甲基-6-(三氟甲基)吡啶-3,4-二胺:
向6-(三氟甲基)吡啶-3,4-二胺(2.0g,12.2mmol)和碳酸钾(3.2g,23.1mmol)于乙腈(10mL)中的溶液中添加碘甲烷(0.8mL)。将反应混合物在30℃下搅拌18小时。将碳酸钾滤掉,将滤液在真空中干燥并用硅胶层析柱(石油:乙酸乙酯=4:3)进行纯化,以提供呈浅黄色固体的标题化合物(0.32g)。1H NMR(400MHz,DMSO-d6):δ(ppm)7.57(s,1H),6.83(s,1H),5.82(s,2H),5.23(d,J=4.8Hz,1H),2.80(d,J=4.8Hz,3H)。19F NMR(300MHz,DMSO-d6):δ(ppm)-60.12(s,3F)。
步骤D:N-[4-氨基-6-(三氟甲基)-3-吡啶基]-3-乙基磺酰基-N-甲基-吡啶-2-甲
酰胺和3-乙基磺酰基-N-[5-(甲基氨基)-2-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺:
向N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(16.70g,87.37mmol)在THF(167.0mL)中的溶液中添加Et3N(22.32g,218.4mmol)。将反应混合物冷却至0℃,并且在0-10℃下,经1小时将溶解于二氯甲烷(170mL)中的3-乙基磺酰基吡啶-2-甲酰氯(18.37g,78.63mmol,如WO2013 018928中所述制备的)滴加到混合物中。1.5小时后,LC/MS在Rt=0.74处检测到所希望的产物。去除冰浴,并且允许将反应混合物加温至环境温度并搅拌12小时。然后将反应混合物用饱和NH4Cl稀释,将有机相分离,并且将水相用二氯甲烷反萃取。将合并的有机相用水、盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩,以给出粗产物。将粗产物溶于二氯甲烷中并吸附在特氟龙散装吸附剂上,并在硅胶柱(Rf200)上用环己烷/乙酸乙酯洗脱进行纯化。这给出粗标题产物作为酰胺区域异构体的混合物,将其不经进一步纯化而用于下一步骤。
LCMS(方法1);Rt=0.73min,[M+H]389和0.8min[M+H]389。
步骤E:2-(3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶:
将来自步骤D的粗产物混合物(26.72g,68.80mmol)在乙酸270mL中的黄色溶液在120℃下搅拌过夜。冷却后,将混合物用甲苯稀释并在真空中浓缩。
将粗产物溶于二氯甲烷中并吸附在特氟龙散装吸附剂上,并在硅胶柱(TORENT)上用庚烷:EtOAc洗脱进行纯化,以给出呈米黄色固体的标题产物。
LCMS(方法1):保留时间0.78分钟,(M+H)=371。1H NMR(400Mhz,氯仿-d)δppm:1.36(t,J=7.3Hz,3H);3.77(q,J=7.3Hz,2H);3.90(s,3H);7.77(dd,J=8.1,4.8Hz,1H);8.12(s,1H);8.55(dd,J=8.1,1.8Hz,1H);9.00(s,1H);9.02(dd,J=4.8,1.8Hz,1H)。
步骤F:2-(3-乙基磺酰基-1-氧化-吡啶-1-鎓-2-基)-3-甲基-6-(三氟甲基)咪唑
并[4,5-c]吡啶(A):
方法A:
向2-(3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(18.70g,50.49mmol)在二氯甲烷(187.0mL)中的溶液中添加间氯过苯甲酸(13.69g,55.53mmol)。将该黄色溶液在环境温度下搅拌18小时。在这时之后,将反应混合物冷却至环境温度,并用水性硫代硫酸钠溶液稀释。将该反应混合物用二氯甲烷萃取,将合并的有机级分用Na2CO3洗涤,经MgSO4干燥,并在真空中浓缩。将粗产物溶于二氯甲烷并吸附在特氟龙散装吸附剂上,并在硅胶柱(TORENT)上用庚烷/乙酸乙酯并且然后用二氯甲烷:甲醇洗脱进行纯化。这给出标题产物作为第一洗脱产物。
LCMS(方法1):保留时间0.72min,(M+H)=387。1H NMR(400Mhz,氯仿-d)δppm;1.35(t,J=7.5Hz,3H);3.39-3.52(m,1H);3.66-3.82(m,1H);3.87(s,3H);7.71(dd,J=8.1,6.6Hz,1H);8.00(dd,J=8.1,0.7Hz,1H);8.13(d,J=0.7Hz,1H);8.55(dd,J=6.6,0.7Hz,1H)9.03(s,1H)。
作为第二洗脱产物的是
2-(3-乙基磺酰基-2-吡啶基)-3-甲基-5-氧化(oxido)-6-(三氟甲基)咪唑并[4,
5-c]吡啶-5-鎓(B):
LCMS(方法1):保留时间0.64min,(M+H)=387。1H NMR(400Mhz,氯仿-d)δppm:1.37(t,J=7.5Hz,3H);3.76(q,J=7.5Hz,2H);3.77(s,3H);7.77(dd,J=8.1,4.8Hz,1H);8.09(s,1H);8.55(dd,J=8.1,1.5Hz,1H);8.71(s,1H);9.01(dd,J=4.8,1.5Hz,1H)。
作为第三洗脱产物分离
2-(3-乙基磺酰基-1-氧化-吡啶-1-鎓-2-基)-3-甲基-5-氧化-6-(三氟甲基)咪唑
并[4,5-c]吡啶-5-鎓(C):
LCMS(方法1):保留时间0.55min,(M+H)=403。1H NMR(400Mhz,氯仿-d)δppm:1.36(t,J=7.3Hz,3H);3.33-3.54(m,1H);3.60-3.80(m,1H);7.72(dd,J=8.1,6.6Hz,1H);7.99(dd,J=8.1,0.7Hz,1H);8.10(s,1H);8.54(dd,J=6.6,0.7Hz,1H);8.68(s,1H)。
产物的比例为(A):(B):(C)9:15:1。
方法B:
在0℃下,向2-(3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(1.00g,2.70mmol)和脲过氧化氢(0.288g,1.10当量,2.97mmol)在二氯甲烷(10.0mL)中的溶液中缓慢添加三氟乙酸酐(1.15g,0.759mL,5.40mmol)。30分钟后,去除冰浴,并且允许将反应混合物加温至环境温度。3小时后的LC/MS在Rt=0.72处检测到所希望的产物,在Rt=0.64处产物B,在Rt=0.55处产物D。将其在环境温度下搅拌过周末。根据方法A进行处理和纯化,给出比例为9:3:1的相同的三种产物(A):(B):(C)。
步骤G:2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]
吡啶
将2-(3-乙基磺酰基-1-氧化-吡啶-1-鎓-2-基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(1.38g,1.00当量,3.57mmol)和磷酰氯(29.61g,18mL,53.5当量,191.2mmol)在微波小瓶中混合并在微波中在130℃下加热6小时。在这个时间之后,LC/MS显示反应完成。将反应混合物在真空中浓缩并在硅胶柱(Rf200)上纯化,用环己烷:乙酸乙酯洗脱,以给出呈白色固体的标题化合物:
LCMS(方法1):保留时间0.95分钟,(M+H)=405/407。1H NMR(400Mhz,氯仿-d)δppm:1.41(t,J=7.5Hz,3H);3.64(q,J=7.5Hz,2H);4.11(s,3H);7.89(d,J=8.4Hz,1H);8.49(d,J=8.4Hz,1H);9.65(s,1H)。
步骤H:2-[3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]-2-吡啶基]-3-甲基-6-
(三氟甲基)咪唑并[4,5-c]吡啶(化合物P3,表P):
将3-(三氟甲基)-1H-吡唑(0.034g,0.25mmol)在DMF(2.0mL,26mmol)中的溶液冷却至0℃并用氢化钠(60%在油中,0.013g,0.32mmol)处理。将该反应在0℃下搅拌20分钟,并且然后用2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(0.10g,0.25mmol)处理并允许将该反应加温并在环境温度下搅拌。30分钟后,LCMS显示反应完成。将该反应用叔丁基二甲醚稀释,并且然后用饱和NaHCO3溶液淬灭。将有机层分离,用水和盐水洗涤2x,经Na2SO4干燥,过滤并在真空中浓缩。将粗产物溶解于二氯甲烷中,吸附在特氟龙散装吸附剂上并且然后在硅胶柱(Rf200)上纯化(用环己烷/乙酸乙酯洗脱),以给出呈白色固体的标题化合物。Mpt.261℃-263℃。
LCMS(方法1):保留时间1.07min,(M+H)=505。1H NMR(400Mhz,氯仿-d)δppm:1.38(t,J=7.5Hz,3H);3.73(q,J=7.5Hz,2H);3.93(s,3H);6.80(d,J=2.6Hz,1H);8.15(d,J=0.7Hz,1H);8.45(d,J=8.8Hz,1H);8.59(dd,J=2.6,0.92Hz,1H)8.68(d,J=8.8Hz,1H)9.04(s,1H)。
实例H2:2-[6-(4-氯苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟甲基)咪唑
并[4,5-c]吡啶(化合物P1,表P):
在SUPELCO小瓶中,将溶解于1,4-二噁烷(1mL)中的2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(步骤G,实例P1,0.04g,0.1mmol)用(4-氯苯基)硼酸(0.02g,0.1mmol)和无水K2CO3(0.04g,0.3mmol)处理并将混合物用氩气吹扫10分钟。然后,添加钯-三-三苯基膦(0.01g,0.01mmol)并将溶液在100℃下加热。4小时后的LCMS分析显示反应完成。将反应混合物用水和乙酸乙酯稀释,将有机层分离,用盐水洗涤,经Na2SO4干燥,过滤并蒸发并在真空中浓缩。将粗产物溶解于二氯甲烷中,吸附在特氟龙散装吸附剂上并且然后在硅胶柱(Rf200)上纯化(用环己烷/乙酸乙酯洗脱),以给出呈黄色固体的标题化合物。Mpt 255℃-256℃。
LCMS(方法1):保留时间1.11min,(M+H)=481/483。1H NMR(400Mhz,氯仿-d)δppm:1.39(t,J=7.5Hz,3H);3.79(q,J=7.5Hz,2H);3.95(s,3H);7.51(d,J=8.8Hz,2H);8.06(d,J=8.8Hz,2H);8.11(d,J=8.4Hz,1H;)8.15(s,1H);8.57(d,J=8.4Hz,1H);9.02(s,1H)。
示例H3:2-[3-乙基磺酰基-6-[(E)-2-[2-(三氟甲基)苯基]乙烯基]-2-吡啶基]-
3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物P2,表P):
在微波小瓶中,将溶解于乙腈中的2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(步骤G,实例P1,0.10g,0.25mmol)、无水K2CO3(0.068g,0.49mmol)、2-(三氟甲基)苯乙烯(0.043g,0.037mL,0.25mmol)用氩气进行脱气。向该混合物中添加乙酸钯(II)(0.0051g,0.022mmol),并且然后将该混合物在140℃下加热45分钟。在这时之后,添加另外部分的2-(三氟甲基)苯乙烯(0.074mL)和乙酸钯(II)(0.0028g,0.050当量,0.012mmol)并将混合物在微波中在140℃下加热1小时。在这时之后,将反应混合物经hyflo过滤,并且将滤液用乙酸乙酯稀释并依次用1N HCl、水和盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗产物溶于二氯甲烷中,吸附在特氟龙散装吸附剂上,并在硅胶柱(Rf200)上用环己烷/乙酸乙酯洗脱进行纯化。通过反相HPLC进一步纯化,给出呈白色泡沫的标题化合物。
LCMS(方法1):保留时间1.14min,(M+H)=541。1H NMR(400Mhz,氯仿-d)δppm:1.40(t,J=7.3Hz,3H);3.86(q,J=7.34Hz,2H);4.00(s,3H);7.24(d,J=15.7Hz,1H);7.46-7.52(m,1H);7.62(t,J=7.5Hz,1H);7.71-7.77(m,2H)7.85(d,J=7.75Hz,1H)8.14(s,1H)8.25(dd,J=15.7,2.20Hz,1H)8.51(d,J=8.4Hz,1H)9.03(s,1H)。
实例H4:2-[3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]-2-吡啶基]-3-
甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物P4,表P)
步骤A:3-乙基硫烷基-5-(三氟甲基)吡啶-2-甲酸甲基酯:
将3-氯-5-(三氟甲基)吡啶-2-甲酸甲基酯(30g,125mmol,CAS登记号码[655235-65-7])的溶液溶解于DMF(630mL)中,分部分添加乙硫醇钠(12.87g,138mmol),保持温度低于20℃。允许将反应混合物搅拌过夜,这之后LCMS分析显示反应完成。将该混合物用水稀释,用AcOEt萃取(3次),并且将合并的有机相依次用饱和水性NH4Cl和盐水洗涤,经MgSO4干燥并在真空中浓缩。将粗标题化合物不经进一步纯化而用于下一步骤。
LCMS(方法1);Rt=0.96min,[M+H]266。1H NMR(400Mhz,氯仿-d)δ
ppm:1.43(t,J=7.5Hz,3H);3.00(q,J=7.5Hz,2H);4.04(s,3H);7.87(d,J=1.1Hz,1H);8.66(d,J=1.1Hz,1H)。
步骤B:3-乙基磺酰基-5-(三氟甲基)吡啶-2-甲酸甲基酯
将3-乙基硫烷基-5-(三氟甲基)吡啶-2-甲酸甲基酯(5.94g,22.4mmol)在二氯甲烷(200mL)中的溶液冷却至0℃。在0℃下,向此溶液中分小部分添加m-CPBA(11.0g,44.8mmol)。2小时后,允许将溶液加温至环境温度并在环境温度下搅拌3小时,这之后LCMS显示反应完成。将反应混合物倒入NaHCO3水性溶液和饱和硫代硫酸钠水性溶液中。然后将混合物用二氯甲烷(3x)萃取,用盐水洗涤,经MgSO4干燥并在真空中浓缩。将粗产物通过Combi快速色谱法用环己烷+0-30%乙酸乙酯的梯度洗脱进行纯化。这给出呈白色固体的标题化合物。
LCMS(方法1);Rt=0.76min,[M+H]298。1H NMR(400Mhz,氯仿-d)δppm:1.39(t,J=7.5Hz,3H);3.57(q,J=7.5Hz,2H);4.08(s,3H);8.61(d,J=1.8Hz,1H);9.11(d,J=1.8Hz,1H)。
步骤C:3-乙基磺酰基-1-氧化-5-(三氟甲基)吡啶-1-鎓-2-甲酸甲基酯
将3-乙基磺酰基-5-(三氟甲基)吡啶-2-甲酸甲基酯(7.5g,25mmol,如上所述制备的)在二氯甲烷(80mL)中的溶液冷却至0℃并且分小部分添加脲过氧化氢络合物(5.1g,53mmol)。向该混合物中添加三氟乙酸酐(11g,7.2mL,50.0mmol),保持反应温度在0℃。允许将反应混合物加温至室温并搅拌过夜。在这时之后,将反应用水性亚硫酸氢钠溶液淬灭,并搅拌15分钟。将所得混合物倒入0.5M HCl中并用二氯甲烷萃取3次。将合并的有机提取物用NaHCO3水性溶液洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗产物通过Combi快速色谱法用环己烷+0-100%乙酸乙酯的梯度洗脱进行纯化,以给出呈白色固体的标题化合物。
LCMS(方法1);Rt=0.70min,[M+H]314。1H NMR(400Mhz,氯仿-d)δppm:1.39(t,J=7.5Hz,3H);3.38(q,J=7.5Hz,2H);4.08(s,3H);7.93(d,J=0.7Hz,1H);8.62(d,J=0.7Hz,1H)。
步骤D:6-氯-3-乙基磺酰基-5-(三氟甲基)吡啶-2-甲酸甲基酯
将3-乙基磺酰基-1-氧化-5-(三氟甲基)吡啶-1-鎓-2-甲酸甲基酯(1.43g,4.57mmol)和磷酰氯(24.3mL)的样品置于两个微波小瓶中,并将小瓶在微波中在130℃下搅拌6小时。在这时之后,将小瓶的内容物合并并且在真空中浓缩。将粗产物在硅胶柱(Rf200)上用环己烷/乙酸乙酯洗脱进行纯化,以给出呈白色晶体的标题产物。
1H NMR(400Mhz,氯仿-d)δppm:1.39(t,J=7.5Hz,3H);3.55(q,J=7.5Hz,2H);4.07(s,3H);8.61(s,1H)。
步骤E:3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酸甲基
酯:
将6-氯-3-乙基磺酰基-5-(三氟甲基)吡啶-2-甲酸甲基酯的溶液(0.285g,0.86mmol)在1,4-二噁烷(7mL)中的溶液用[4-(三氟甲基)苯基]硼酸(0.212g,1.12mmol)和无水K2CO3(0.356g,3.00当量,2.58mmol)处理并将混合物用氩气吹扫10分钟。向该混合物中添加四(三苯基膦)钯(0)(0.0993g,0.100当量,0.0859mmol)并将该溶液在100℃下加热3小时,这个时间之后LCMS显示良好的反应转化率。将该反应混合物用NH4Cl饱和溶液、水和乙酸乙酯稀释。将有机相分离,用盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗产物溶解于二氯甲烷中并吸附在特氟龙散装吸附剂上。在硅胶柱(Rf200)上用环己烷/乙酸乙酯洗脱进行纯化,给出呈白色固体的标题化合物。
LCMS(方法1);Rt=1.09min,[M+H]442。1H NMR(400Mhz,氯仿-d)δppm:1.44(t,J=7.5Hz,3H);3.59(q,J=7.5Hz,2H);4.06(s,3H);7.70(d,J=8.0Hz,2H);7.78(d,J=8.0Hz,2H);8.73(s,1H)。
步骤F:3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酸:
在环境温度下,将3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酸甲基酯(0.28g,0.63mmol)溶解于四氢呋喃/H2O 3:1(10mL)中并用氢氧化锂水合物(0.028g,0.67mmol)处理。搅拌3小时后的LCMS分析显示反应。将反应混合物在真空中浓缩并吸收在乙酸乙酯和10%水性HCl中。将有机层分离并用盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩,以给出呈米黄色固体的标题化合物,将其不经进一步纯化而用于下一步骤。
LCMS(方法1);Rt=0.88min,[M+H]428。1H NMR(400Mhz,氯仿-d)δppm 1.42(t,J=7.3Hz,3H):3.75(q,J=7.3Hz,2H):4.98(br.s.,1H);7.70(d,J=7.8Hz,2H);7.79(d,J=7.8Hz,2H):8.86(s,1H)。
步骤G:3-乙基磺酰基-N-[5-(甲基氨基)-2-(三氟甲基)-4-吡啶基]-5-(三氟甲
基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酰胺和N-[4-氨基-6-(三氟甲基)-3-吡啶基]-3-乙
磺酰基-N-甲基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酰胺:
将3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酸(0.10g,0.23mmol)、EDCI(0.049g,0.26mmol)和N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(0.049g,0.26mmol,步骤C,实例P1)在吡啶(3.0mL)中的溶液在120℃下搅拌。2小时后,LC/MS显示足够的反应进展用于处理。将反应混合物倒入水中并用乙酸乙酯(X3)萃取。将合并的有机层用盐水洗涤,经Na2SO4干燥并在真空中浓缩。将粗产物溶解于二氯甲烷中并吸附在特氟龙散装吸附剂上。在硅胶柱(Rf200)上纯化,用环己烷/乙酸乙酯梯度洗脱,给出呈黄色固体的标题化合物的混合物。
LCMS(方法1);Rt=1.10min,[M+H]601;Rt=1.14min,[M+H]601;
步骤H:2-[3-乙基磺酰基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]-2-吡啶基]-3-
甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(化合物P4,表P):
将3-乙基磺酰基-N-[5-(甲基氨基)-2-(三氟甲基)-4-吡啶基]-5-(三氟甲基)-4-吡啶基]-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酰胺和N-[4-氨基-6-(三氟甲基)-3-吡啶基]-3-乙基磺酰基-N-甲基-5-(三氟甲基)-6-[4-(三氟甲基)苯基]吡啶-2-甲酰胺(0.055g,0.092mmol)在乙酸(1mL)中的黄色溶液在120℃下搅拌18小时。在这时之后,LCMS分析显示反应完成。将反应混合物冷却至环境温度,用甲苯稀释并在真空中浓缩。将粗产物溶解于二氯甲烷中并吸附在特氟龙散装吸附剂上。在硅胶柱(Rf200)上用环己烷/乙酸乙酯梯度洗脱进行纯化,给出呈白色固体的标题化合物的混合物。Mpt.140℃-142℃。
LCMS(方法1);Rt=1.17min,[M+H]583。1H NMR(400Mhz,氯仿-d)δppm 1.47(t,J=7.5Hz,3H);3.94(q,J=7.5Hz,2H);7.72-7.76(m,2H);7.78-7.82(m,2H);3.94(q,J=7.34Hz,2H);3,96(s,3H);8.92(s,1H);9.01(s,1H)。
实例H5:2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并
[4,5-c]吡啶(化合物P15,表P)
步骤A:3,6-二氯吡啶-2-甲酰氯
将3,6-二氯吡啶-2-甲酸(5.00g,24.7mmol)的样品在二氯甲烷(200mL)中稀释,并添加二甲基甲酰胺(0.124mL,1.6mmol)。在室温下,在10分钟内(气体逸出)向该溶液中滴加草酰氯(3.15mL,34.6mmol)。将该反应混合物在室温下搅拌,并且2.5小时后添加另外的1ml草酰氯并继续搅拌1小时。在这时之后,将反应混合物在真空中浓缩并不经进一步纯化而用于下一步骤。
步骤B:3,6-二氯-N-[5-(甲基氨基)-2-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺
向N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(52.0g,272mmol)在四氢呋喃(260mL)中的溶液中添加三乙胺(95.8mL,680mmol)。将该红色溶液冷却至0℃,并在0-10℃下,在90分钟内滴加在二氯甲烷(156mL)中的3,6-二氯吡啶-2-甲酰氯(51.5g,245mmol)。1小时后去除冰浴,并且将混合物在室温下搅拌。2小时后,LC-MS分析显示主要所希望的物质。将反应混合物搅拌过夜,并且然后用NH4Cl饱和溶液洗涤,并将混合物在真空中浓缩以去除四氢呋喃。然后将残余物用1.2L二氯甲烷(800mL)乙酸乙酯和再1L二氯甲烷萃取。将合并的有机层经Na2SO4干燥,过滤并在真空中浓缩,以给出呈棕色固体的标题化合物。
LCMS(方法1):366(M+H+);保留时间:0.83min。
步骤C:2-(3,6-二氯-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶
将3,6-二氯-N-[5-(甲基氨基)-2-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺(99.3g,272mmol)在乙酸(298mL)中的黄色溶液在110℃浴温下搅拌16小时。允许该反应混合物到室温,这个时间之后LC-MS分析显示所希望的物质。添加甲苯并将混合物在真空中浓缩。向残余物中添加环己烷和二氯甲烷,并且将所获得的混合物在真空下在50℃下在800mbar下进行搅拌。将浆液进一步用环己烷稀释,并且将固体在泵上过滤。将滤饼用环己烷(与少量DCM混合)洗涤并在真空下干燥。添加甲苯,并且将混合物蒸发并在60℃和20mbar真空下干燥以去除痕量的乙酸,给出呈棕色固体的标题化合物。
LCMS(方法1):348(M+H+);保留时间:0.95min。
1H NMR(400Mhz,氯仿-d)δppm 4.04(s,3H)7.51(d,J=8.44Hz,1H)7.93(d,J=8.44Hz,1H)8.19(s,1H)8.99(s,1H)
步骤D:2-(6-氯-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]
吡啶
在氩气下,将2-(3,6-二氯-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(1.14g,3.28mmol)的样品溶解于四氢呋喃中。在室温下分批添加乙硫醇钠(0.311g,3.28mmol)。将褐色反应混合物在室温下搅拌2小时,此时LC-MS分析显示反应完成,形成了所希望的产物。将反应混合物用NH4Cl处理,然后用水和乙酸乙酯处理。将有机层分离,用水和盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗品通过硅胶快速色谱法进行纯化,以给出呈米黄色固体的标题化合物。
LCMS(方法1):373(M+H+);保留时间:1.02min。
1H NMR(400Mhz,氯仿-d)δppm 1.35(t,J=7.34Hz,3H)2.97(q,J=7.34Hz,2H)4.11(s,3H)7.44(d,J=8.44Hz,1H)7.76(d,J=8.44Hz,1H)8.20(d,J=0.73Hz,1H)8.97(s,1H)
步骤E:2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]
吡啶
在0℃下,将m-CPBA(2.35g,10.5mmol)添加到2-(6-氯-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(1.86g,4.99mmol)在氯仿(46.5mL)中的溶液中。添加后,将冰浴保持10分钟,并且然后允许将乳状溶液加温至室温。将反应混合物在室温下搅拌一夜。在这时之后,再添加一部分M-CPBA(1.12g,4.99mmol),将混合物在室温下搅拌2小时。LC-MS分析显示反应完成。添加饱和硫代硫酸钠水性溶液和饱和水性NaHCO3并将混合物搅拌1小时。将有机层分离,用NaHCO3萃取,经Na2SO4干燥并蒸发。将粗产物通过硅胶快速色谱法进行纯化,以给出呈白色固体的标题化合物。
LCMS(方法1):406(M+H+);保留时间:0.95min。
1H NMR(400Mhz,氯仿-d)δppm 1.37(t,J=7.34Hz,3H)3.79(q,J=7.46Hz,2H)3.94(s,3H)7.75(d,J=8.44Hz,1H)8.11(s,1H)8.47(d,J=8.44Hz,1H)9.00(s,1H)
步骤F:2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,
5-c]吡啶(化合物P15,表P)
在supelco小瓶中,将2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(0.40g,0.99mmol)溶解于1,4-二噁烷(10mL,120mmol)中。添加环丙基硼酸(0.18g,2.0mmol)和碳酸钾(0.41g,3.0mmol),并将混合物用氩气吹扫。然后添加四(三苯基膦)钯(0.11g,0.099mmol),将小瓶加盖并且将褐色溶液在100℃下加热19小时。LC-MS分析显示形成所希望的产物。添加水和乙酸乙酯,将有机层分离,用盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将获得的粗品通过硅胶快速色谱法进行纯化。将获得的混合物溶解于乙酸乙酯中,并再次用NaHCO3洗涤。将有机层用盐水洗涤,经Na2SO4干燥,过滤并蒸发。将获得的固体再次通过反相进行纯化,以给出呈白色固体的标题化合物。
LCMS(方法1):411(M+H+);保留时间:1.01min。
1H NMR(400Mhz,氯仿-d)δppm 1.11-1.13(m,1H)1.11-1.23(m,4H)1.33(t,J=7.34Hz,3H)2.22(ddd,J=7.70,4.77,2.93Hz,1H)3.70(q,J=7.34Hz,2H)3.84(s,3H)7.54(d,J=8.44Hz,1H)8.09(s,1H)8.30(d,J=8.44Hz,1H)8.97(s,1H)
实例H6:2-[6-(3,5-二氟苯基)-3-乙基磺酰基-2-吡啶基]-3-甲基-6-(三氟甲基)
咪唑并[4,5-c]吡啶(化合物P8,表P)
在supelco小瓶中,将2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(100mg,0.2470mmol)、(3,5-二氟苯基)硼酸(46mg,0.2964mmol)和碳酸钾(102mg,0.7411mmol)溶解于1,4-二噁烷(2.5mL)中。将所得混合物用氩气冲洗5分钟。在这时之后,添加四(三苯基膦)钯(28mg,0.02470mmol),并且将小瓶封闭并在95℃下加热16小时。LC-MS分析显示反应完成。将反应混合物冷却至室温并用水淬灭。将水层用乙酸乙酯萃取。将合并的有机层用NaHCO3的饱和溶液和饱和NaCl溶液洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗品通过硅胶快速色谱法进行纯化,以给出呈黄色固体的标题化合物。
LCMS(方法1):483(M+H+);保留时间:1.09min。
1H NMR(400Mhz,氯仿-d)δppm 1.42(t,J=7.34Hz,3H)3.84(q,J=7.34Hz,2H)3.99(s,3H)7.00-7.05(m,1H)7.68(d,J=5.87Hz,2H)8.12(d,J=8.44Hz,1H)8.17(s,1H)8.64(d,J=8.44Hz,1H)9.06(s,1H)
实例H7:2-[3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]-2-吡啶基]-3-甲基-6-
(三氟甲基硫烷基)咪唑并[4,5-c]吡啶(化合物P9,表P)
步骤A:3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]吡啶-2-甲酸甲基酯
向6-氯-3-乙基磺酰基-吡啶-2-甲酸甲基酯(526mg,2mmol)、3-(三氟甲基)-1H-吡唑(1.361g,10mmol)在二噁烷(25mL)中的搅拌溶液中添加CuI(38mg,0.2mmol)、N,N'-二甲基乙二胺(880mg,1mmol)和碳酸钾(1.38g,10mmol)。将反应体系在氮气气氛下在120℃下回流4小时。冷却至室温后,将反应混合物过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1HNMR(400MHz,CDCl3):δppm 1.36(t,3H),3.49(q,2H),4.06(s,3H),6.69(s,1H),8.26(d,J=8.4Hz,1H),8.44(d,J=8.4Hz,1H),8.68(s,1H);ESI-MS(+):386(M+Na)+
步骤B:3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]吡啶-2-甲酸
向3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]吡啶-2-甲酸甲基酯(218mg,0.6mmol)在THF(10mL)中的搅拌溶液中添加NaOH(120mg,3mmol)和H2O(30mL)。将该反应体系在室温下搅拌2小时。在这时之后,用HCl将pH值调节至2,并且将反应混合物用乙酸乙酯萃取3次。将合并的有机层经无水硫酸钠干燥,过滤并在真空中浓缩,以给出标题化合物。
1HNMR(400MHz,DMSO-d6):δppm 1.18(t,3H),3.54(q,2H),7.12(s,1H),8.21(d,J=8.8Hz,1H),8.53(d,J=8.4Hz,1H),8.86(s,1H);ESI-MS(+):348(M-H)-
步骤C:2-[3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]-2-吡啶基]-3-甲基-6-
(三氟甲基硫烷基)咪唑并[4,5-c]吡啶(化合物P9,表P)
向3-乙基磺酰基-6-[3-(三氟甲基)吡唑-1-基]吡啶-2-甲酸(180mg,0.52mmol)、N3-甲基-6-(三氟甲基硫烷基)吡啶-3,4-二胺(250mg,1.11mmol)和HATU(0.78g,2mmol)在DMF(30mL)中的搅拌溶液中添加DIPEA(2mL,10mmol)。将反应混合物在室温下搅拌过夜。然后将该反应混合物用乙酸乙酯和H2O稀释,将有机层用盐水洗涤,经无水硫酸钠干燥,过滤并在真空中浓缩。将粗产物不经进一步纯化而用于下一步骤。将粗产物在乙酸(20mL)中的溶液在120℃下回流24小时。然后将反应混合物蒸发至干。将残余物通过硅胶色谱法(石油:EtOAc=4:1)进行纯化,以给出呈白色固体的标题化合物。
LCMS(方法1):537(M+H+);保留时间:1.17min。
1HNMR(400MHz,CDCl3):δ(ppm)1.37(t,3H),3.73(q,2H),3.90(s,3H),6.79(s,1H),8.14(s,1H),8.45(d,J=4.8Hz,1H),8.65(s,1H),8.67(d,J=4.8Hz,1H),8.98(s,1H);19FNMR(376MHz,CDCl3):δ(ppm)-46.40(s,3F),-68.19(s,3F)
实例2-(3-乙基磺酰基-6-嘧啶-2-基-2-吡啶基)-3-甲基-6-(三氟甲基硫烷基)咪
唑并[4,5-c]吡啶(化合物P10,表P)
步骤A:N-甲基-4-硝基-6-(三氟甲基硫烷基)吡啶-3-胺
将(bpy)CuSCF3(14.4g,45mmol)和6-溴-N-甲基-4-硝基-吡啶-3-胺(6.96g,30mmol)在120mL CH3CN中的样品在氮气下回流48小时。将反应混合物从油浴中去除并允许冷却至室温,并且然后通过SiO2过滤。将硅胶用二乙醚洗脱并在真空中浓缩。将残余物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1HNMR(400MHz,DMSO-d6):δ(ppm)3.10(d,J=5.2Hz,3H),8.21(s,1H)8.49(q,1H),8.67(s,1H);19FNMR(376MHz,DMSO-d6):δ(ppm)-36.79(s,3F);ESI-MS:252(M-H)-。
步骤B:N3-甲基-6-(三氟甲基硫烷基)吡啶-3,4-二胺
向N-甲基-4-硝基-6-(三氟甲基硫烷基)吡啶-3-胺(3.42g,13.5mmol)在甲醇(50mL)中的溶液中添加拉尼镍(20%wt)。在室温下,向该混合物中滴加水合肼(10mL)。将反应混合物在室温下搅拌30分钟。将拉尼镍通过硅藻土过滤出;将滤液在真空中干燥并用硅胶色谱柱纯化,以得到呈白色固体的标题化合物。
1HNMR(400MHz,DMSO-d6):δppm 2.78(d,J=5.2Hz,3H),5.20(q,1H),5.77(s,2H),6.82(s,1H),7.53(s,1H);19FNMR(376MHz,DMSO-d6):δppm-45.49(s,3F);ESI-MS(+):224(M+H)+。
步骤C:3,6-二氯吡啶-2-甲酸甲基酯
在室温下,向3,6-二氯吡啶-2-甲酸(76.8g,0.4mol)在甲醇(500mL)中的溶液中滴加SOCl2(150mL)。将反应混合物在室温下搅拌3小时。在这时之后,将反应混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩,以给出标题化合物。
1HNMR(400MHz,DMSO-d6):δppm 3.90(s,3H),7.80(d,J=8.8Hz,1H),8.20(d,J=8.8Hz,1H);ESI-MS(+):228(M+Na)+。
步骤D:6-氯-3-乙基硫烷基-吡啶-2-甲酸甲基酯
在0℃下,向3,6-二氯吡啶-2-甲酸甲基酯(16g,77.6mmol)在DMF(150mL)中的溶液中添加乙硫醇钠(7.2g,85.8mmol)。添加后,将反应混合物在室温下搅拌30分钟。在这时之后,LCMS分析显示反应完成。将反应混合物倒入水中,并且过滤形成的沉淀物并在红外线烘箱下干燥,以得到呈白色固体的标题化合物。
1HNMR(400MHz,CDCl3):δppm 1.38(t,3H),2.92(q,2H),3.98(s,3H),7.40(d,J=8.8Hz,1H),7.66(d,J=8.8Hz,1H);ESI-MS(+):254(M+Na)+。
步骤E:6-氯-3-乙基磺酰基-吡啶-2-甲酸甲基酯
将6-氯-3-乙基硫烷基-吡啶-2-甲酸甲基酯(11.55g,50mmol)和m-CPBA(25.8g,150mmol)在200mL二氯甲烷中的溶液在室温下搅拌2小时。在这时之后,将混合物倒入NaHCO3和Na2SO3的饱和溶液中,并用DCM萃取三次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1HNMR(400MHz,CDCl3):δppm 1.33(t,3H),3.51(q,2H),4.02(s,3H),7.63(d,J=8Hz,1H),8.29(d,J=8Hz,1H);ESI-MS(+):286(M+Na)+。
步骤F:3-乙基磺酰基-6-嘧啶-2-基-吡啶-2-甲酸甲基酯
向6-氯-3-乙基磺酰基-吡啶-2-甲酸甲基酯(526mg,2mmol)和三丁基(嘧啶-2-基)锡烷(1.107g,3mmol)在二噁烷(25mL)中的搅拌溶液中添加CuI(76mg,0.4mmol)和PdCl2(PPh3)2(140mg,0.2mmol)。将反应混合物在氮气气氛下在120℃下回流4小时。冷却至室温后,将反应混合物过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1HNMR(400MHz,CDCl3):δppm 1.36(t,3H),3.58(q,2H),4.05(s,3H),7.42(t,1H),8.53(d,J=8.4Hz,1H),8.81(d,J=8.4Hz,1H),9.00(d,J=4.8Hz,2H);ESI-MS(+):330(M+Na)+
步骤G:3-乙基磺酰基-6-嘧啶-2-基-吡啶-2-甲酸
向3-乙基磺酰基-6-嘧啶-2-基-吡啶-2-甲酸甲基酯(522mg,1.7mmol)在四氢呋喃(10mL)中的搅拌溶液中添加NaOH(340mg,8.5mmol)和水(30ml)。将该反应体系在室温下搅拌2小时,此时LCMS分析显示反应完成。用HCl将pH值调节至2,并且将反应混合物用乙酸乙酯萃取三次。将有机层经无水硫酸钠干燥,过滤并在真空中浓缩,以给出标题化合物。
1HNMR(400MHz,DMSO-d6):δppm 1.22(t,3H),3.57(q,2H),7.66(m,1H),7.68(d J=4.8Hz,1H),8.55(d,J=8.4Hz,1H),8.70(d,J=8.4Hz,1H),9.07(d,J=4.8Hz,2H)。
步骤H:2-(3-乙基磺酰基-6-嘧啶-2-基-2-吡啶基)-3-甲基-6-(三氟甲基硫烷基)
咪唑并[4,5-c]吡啶(化合物P10,表P)
向3-乙基磺酰基-6-嘧啶-2-基-吡啶-2-甲酸(470mg,1.6mmol)、N3-甲基-6-(三氟甲基硫烷基)吡啶-3,4-二胺(430mg,1.92mmol)和HATU(1.216g,3.2mmol)在DMF(30mL)中的搅拌溶液中添加DIPEA(2.8ml,16mmol)。将该反应体系在室温下搅拌过夜。在这时之后,将该反应混合物用乙酸乙酯和H2O稀释,并且将有机层用盐水洗涤,经无水硫酸钠干燥并且在真空中浓缩。将粗产物不经进一步纯化而用于下一步骤。
将粗产物在乙酸(20mL)中的溶液在120℃下回流24小时。将反应混合物蒸发至干,并且将残余物通过硅胶色谱法进行纯化,以得到呈白色固体的标题化合物。
LCMS(方法1):481(M+H+);保留时间:0.93min
1HNMR(400MHz,CDCl3):δ(ppm)1.38(t,3H),3.80(q,2H),3.93(s,3H),7.44(t,1H),8.10(s,1H),8.70(d,J=8.4Hz,1H),8.96(m,2H),9.0(d,J=4.8Hz,2H);19FNMR(376MHz,CDCl3):δ(ppm)-45.77(s,3F);
实例H8:2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基硫烷基)咪
唑并[4,5-c]吡啶(化合物P13,表P)
步骤A:6-环丙基-3-乙基硫烷基-吡啶-2-甲酸甲基酯
向6-氯-3-乙基硫烷基-吡啶-2-甲酸甲基酯(462mg,2mmol)、环丙基硼酸(344mg,4mmol)在二噁烷(25mL)中的搅拌溶液中添加碳酸钾(552mg,4mmol)和Pd(PPh3)4(230mg,0.2mmol)。将该反应体系在氮气气氛下在120℃下回流24小时。冷却至室温后,将反应混合物过滤并在真空中浓缩。将粗产物通过硅胶柱层析法纯化,以给出标题化合物。
1HNMR(400MHz,CDCl3):δ(ppm)0.98(m,4H),1.32(t,3H),2.08(m,1H),2.88(q,2H),3.95(s,3H),7.08(d,J=8.4Hz,1H),7.57(d,J=8Hz,1H);ESI-MS(+):260(M+Na)+。
步骤B:6-环丙基-3-乙基硫烷基-吡啶-2-甲酸
向6-环丙基-3-乙基硫烷基-吡啶-2-甲酸甲基酯(320mg,1.35mmol)在THF(10mL)中的搅拌溶液中添加NaOH(280mg,7mmol)和H2O(30mL)。将该反应体系在室温下搅拌4小时。用HCl将pH值调节至2,并且将反应混合物用乙酸乙酯萃取三次。将合并的有机层经无水硫酸钠干燥,过滤并在真空中浓缩,以给出标题化合物。
1HNMR(400MHz,DMSO-d6):δppm 0.93(m,4H),1.18(t,3H),2.07(m,1H),2.91(q,2H),7.36(d,J=8.0Hz,1H),7.73(d,J=8.4Hz,1H),12.93(bs,1H);ESI-MS(-):222(M-H)-。
步骤C:6-溴-2-(6-环丙基-3-乙基硫烷基-2-吡啶基)-3-甲基-咪唑并[4,5-c]吡
啶
向6-环丙基-3-乙基硫烷基-吡啶-2-甲酸(280mg,1.25mmol)、6-溴-N3-甲基-吡啶-3,4-二胺(303mg,1.5mmol)和HATU(0.78g,2mmol)在DMF(30mL)中的搅拌溶液中添加DIPEA(2mL,10mmol)。将反应混合物在室温下搅拌过夜。然后将该反应混合物用乙酸乙酯和H2O稀释,并且将有机层用盐水洗涤,经无水硫酸钠干燥,过滤并在真空中浓缩。将粗产物不经进一步纯化而用于下一步骤。将粗产物在乙酸(20mL)中的溶液在120℃下回流24小时。将该反应混合物浓缩,并通过硅胶柱色谱法进行纯化,以得到呈白色固体的标题化合物。
1HNMR(400MHz,CDCl3):δ(ppm)1.04(m,4H),1.31(t,3H),2.1(m,1H),2.91(q,2H),3.92(s,3H),7.25(d,J=8.4Hz,1H),7.66(d,J=8Hz,1H),7.94(s,1H),8.62(s,1H);ESI-MS(+):413(M+Na)+。
步骤D:6-溴-2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-咪唑并[4,5-c]吡
啶(化合物P12,表P)
将6-溴-2-(6-环丙基-3-乙基硫烷基-2-吡啶基)-3-甲基-咪唑并[4,5-c]吡啶(285mg,0.73mmol)和m-CPBA(630mg,3.66mmol)在40mL的DCM中的样品在室温下搅拌2小时。然后将混合物倒进水中的NaHCO3和Na2SO3的饱和溶液中,并且用二氯甲烷萃取三次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
LCMS(方法1):421/423(M+H+);保留时间:0.97min
1HNMR(400MHz,CDCl3):δ(ppm)1.16(m,4H),1.34(t,3H),2.05(m,1H),3.69(q,2H),3.76(s,3H),7.53(d,J=8.0Hz,1H),7.86(s,1H),8.30(d,J=8.4Hz,1H),8.66(s,1H);
步骤E:2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基硫烷基)咪
唑并[4,5-c]吡啶(化合物P13,表P)
将(bpy)CuSCF3(410mg,1.28mmol)和6-溴-2-(6-环丙基-3-乙基磺酰基-2-吡啶基)-3-甲基-咪唑并[4,5-c]吡啶(270mg,0.64mmol)在20mL的CH3CN中的样品在氮气下回流48小时。将反应混合物从油浴中去除并允许冷却,并通过SiO2过滤,用二乙醚洗脱。将滤液用盐水洗涤并在真空中浓缩。将残余物通过硅胶柱色谱法进行纯化,以给出标题化合物。
LCMS(方法1):444(M+H+);保留时间:1.07min
1HNMR(400MHz,CDCl3):δ(ppm)1.19(m,4H),1.34(t,3H),2.12(m,1H),3.71(q,2H),3.81(s,3H),7.54(d,J=8.4Hz,1H),8.10(s,1H),8.31(d,J=8.8Hz,1H),8.92(s,1H)
实例H9:6-(6-环丙基-3-乙基硫烷基-2-吡啶基)-7-甲基-3-(三氟甲基)咪唑并
[4,5-c]哒嗪(化合物P22,表P)
步骤A:3-氯-6-碘哒嗪
将氢碘酸(250mL)添加到3,6-二氯哒嗪(149g,1mol)和NaI(180g,1.2mol)在500mL的CHCl3中的混合物中。添加后,将混合物在环境温度下搅拌24小时,并且倒入水中,并用二氯甲烷萃取3次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩,以给出标题化合物。
1H-NMR(400Mz,DMSO-d6)δ:7.63(d,1H),8.16(d,1H)。
步骤B:3-氯-6-(三氟甲基)哒嗪
在氮气下,将TMSCF3(198.8g,1.4mol)添加到3-氯-6-碘哒嗪(240g,1mol)、KF(81g,1.4mol)和CuI(228g,1.2mol)在1L的DMF中的混合物中。添加后,将该混合物在50℃下搅拌2小时。然后将该混合物倒入水中并且用乙醚萃取(三次)。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将残余物通过硅胶快速柱色谱法进行纯化,以给出标题化合物。
1H-NMR(400Mz,DMSO-d6)δ:8.30(d,1H),8.38(d,1H);19F-NMR(400Mz,DMSO-d6)δ:-64.93(s,3F)。
步骤C:N-甲基-6-(三氟甲基)哒嗪-3-胺:
将MeNH2(100g,30%在EtOH中)的溶液添加到3-氯-6-(三氟甲基)哒嗪(91g,0.5mol)在100ml的EtOH中的混合物中。添加后,将该混合物在50℃下搅拌2小时并且然后倒入水中。将沉淀的固体过滤并在真空中干燥,以给出标题化合物。
1H-NMR(400Mz,DMSO-d6)δ:2.93(d,3H),6.95(d,1H),7.58(q,1H),7.63(d,1H);19F-NMR(400Mz,DMSO-d6)δ:-59.88(s,3F);ESI-MS(+):178(M+H)+。
步骤D:4-溴-N-甲基-6-(三氟甲基)哒嗪-3-胺:
将溴(32g,0.2mol)添加到N-甲基-6-(三氟甲基)哒嗪-3-胺(17.7g,0.1mol)在100mL的MeCN中的混合物中。在添加之后,将该混合物在环境温度下搅拌48小时。在这时之后,将该混合物倒入氢氧化铵(10%溶液)中并用乙酸乙酯萃取(三次)。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将残余物通过硅胶快速柱色谱法进行纯化,以给出标题化合物。
1H-NMR(400Mz,DMSO-d6)δ:3.03(d,3H),7.45(q,1H),8.23(s,1H);19F-NMR(400Mz,DMSO-d6)δ:-59.47(s,3F);ESI-MS(+):256/258(M+H)+。
步骤E:N3-甲基-6-(三氟甲基)哒嗪-3,4-二胺:
将4-溴-N-甲基-6-(三氟甲基)哒嗪-3-胺(3g,11.8mmol)和120mL的氢氧化铵置于250mL高压釜中。然后,将氮气引入高压釜中,并且将压力升高至2MPa。将混合物在130℃下搅拌48小时,倒入水中,并用乙酸乙酯萃取(三次)。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将残余物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1H-NMR(400Mz,DMSO-d6)δ:2.97(d,3H),6.27(s,2H),6.50(q,1H),6.67(s,1H);19F-NMR(400Mz,DMSO-d6)δ:-61.96(s,3F);ESI-MS(+):193(M+H)+。
步骤F:6-环丙基-3-乙基硫烷基-吡啶-2-甲酰氯
向6-环丙基-3-乙基硫烷基-吡啶-2-甲酸(223mg,1mmol)在10mL二氯甲烷中的混合物中添加草酰氯(380mg,3mmol)并且在室温下搅拌30分钟。在减压下去除过量的草酰氯和二氯甲烷,以给出几乎定量产量的标题化合物(241mg)。将粗标题化合物不经进一步纯化而直接用于下一步骤。
步骤G:6-(6-环丙基-3-乙基硫烷基-2-吡啶基)-7-甲基-3-(三氟甲基)咪唑并[4,
5-c]哒嗪(化合物P22,表P)
将6-环丙基-3-乙基硫烷基-吡啶-2-甲酰氯(241mg,1mmol)的样品添加到N3-甲基-6-(三氟甲基)哒嗪-3,4-二胺(211mg,1.1mmol)在20mL的THF中的混合物中,并将该混合物回流48小时。在这时之后,将混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
1H NMR(400MHz,DMSO)δ0.97-1.00(m,2H),1.02-1.07(m,2H),1.19(t,3H),2.22-2.28(m,1H),2.98(q,2H),4.08(s,3H),7.58(d,1H),7.98(d,1H),8.71(s,1H);19F NMR(400MHz,DMSO)δ-62.23(s,3F);ESI-MS(+):380(M+H)+,434(M+Na+MeOH)+。
实例H10:6-(6-环丙基-3-乙基磺酰基-2-吡啶基)-7-甲基-3-(三氟甲基)咪唑并
[4,5-c]哒嗪(化合物P14,表P)
将6-(6-环丙基-3-乙基硫烷基-2-吡啶基)-7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪(70mg,0.18mmol)和m-CPBA(93mg,0.54mmol)在10mL二氯甲烷中的溶液在室温下搅拌2小时。然后将混合物倒入水中的NaHCO3和Na2SO3的饱和溶液中,并且用乙酸乙酯萃取三次。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过硅胶柱色谱法进行纯化,以给出标题化合物。
LCMS(方法1):413(M+H+);保留时间:1.01min。
1H NMR(400MHz,DMSO-d6)δ1.05-1.07(m,2H),1.13-1.18(m,2H),1.15(t,3H),2.38-2.42(m,1H),3.63(q,2H),3.88(s,3H),7.88(d,1H),8.34(d,1H),8.72(s,1H);19F-NMR(400Mz,DMSO-d6)δ:-64.55(s,3F);
实例H11:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-
基]-2-吡啶基]乙腈(化合物P23,表P)
在微波小瓶中,将2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(0.20g,0.49mmol)溶解于DMF(1.0mL)中。用氩气冲洗小瓶,并添加TMSCN(0.10mL,0.74mmol)、二氟锌(0.031g,0.30mmol)、Pd2(dba)3(0.0091g,0.0099mmol)和XANTPHOS(0.012g,0.020mmol)。将小瓶加盖并在微波中在140℃下加热30分钟。将该反应混合物用乙酸乙酯稀释,并且经hyflo过滤。将滤液用水和盐水萃取,经Na2SO4干燥,过滤并在真空中浓缩。将粗产物通过硅胶快速色谱法进行纯化,以给出标题化合物。
LCMS(方法1):410(M+H+);保留时间:0.84min。
1H NMR(400Mhz,氯仿CHLOROFORM-d)δppm 1.40(t,J=7.52Hz,3H)3.83(q,J=7.34Hz,2H)3.97(s,3H)4.17(s,2H)7.89(d,J=8.44Hz,1H)8.15(s,1H)8.63(d,J=8.07Hz,1H)9.04(s,1H)
实例H12:1-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-
基]-2-吡啶基]环丙腈(化合物P17,表P)
将2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-2-吡啶基]乙腈(0.11g,0.27mmol)的样品溶解于乙腈(2.8mL)中。添加碳酸铯(0.27g,0.81mmol),然后添加1,2-二溴乙烷(0.047mL,0.54mmol)。将该混合物在80℃搅拌1小时。LC-MS分析显示起始物质的消耗和所希望的产物的物质。将反应用水和乙腈淬灭并蒸发。将残余物用乙酸乙酯稀释,用水和盐水洗涤,经经Na2SO4干燥,过滤并在真空中浓缩。将粗产物通过硅胶快速色谱法进行纯化,以给出标题化合物。
LCMS(方法1):436(M+H+);保留时间:0.94min。
1H NMR(400Mhz,氯仿-d)δppm 1.38(t,J=7.52Hz,3H)1.88-2.02(m,4H)3.73(d,J=7.70Hz,2H)3.86(s,3H)8.12-8.19(m,2H)8.54(d,J=8.44Hz,1H)9.02(s,1H)
实例H13:2-[3-乙基磺酰基-6-[2-(3-氟苯基)乙炔基]-2-吡啶基]-3-甲基-6-(三
氟甲基)咪唑并[4,5-c]吡啶(化合物P20,表P)
将2-(6-氯-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(0.10g,0.25mmol)、1-乙炔基-3-氟-苯(0.044mL,0.37mmol)、DIPEA(0.086mL,0.49mmol)、碘化铜(I)(0.0024g,0.012mmol)在四氢呋喃(4.0mL)中的样品在小瓶中混合,并将该澄清的淡黄色溶液用氩气冲洗。添加PdCl2(PPH3)2(0.0088g,0.012mmol),并且将混合物在室温下搅拌过夜。在这时之后,反应显示完成。将粗混合物通过快速色谱法进行纯化,以给出呈米黄色固体的标题化合物。
LCMS(方法1):489(M+H+);保留时间:1.11min。
1H NMR(400Mhz,氯仿-d)δppm 1.39(t,J=7.34Hz,3H)3.78(q,J=7.46Hz,2H)3.96(s,3H)7.14-7.24(m,1H)7.32-7.38(m,1H)7.37-7.48(m,2H)7.92(d,J=8.44Hz,1H)8.14(s,1H)8.54(d,J=8.44Hz,1H)9.02(s,1H)
表1-88中的化合物可以按上述方法类似地制备。
表P:具有化学式(I)的化合物的实例
通过添加其他有杀昆虫、杀螨和/或杀真菌活性的成分,根据本发明的这些组合物的活性可以显著地加宽,并且适合于当时的环境。具有化学式I的化合物与其他具有杀昆虫、杀螨和/或杀真菌活性的成分的混合物还可以具有进一步地、意料之外的优点,这些优点还可以在更宽的含义上描述为协同活性。例如,植物对其更好的耐受性、降低的植物毒性,昆虫可以在它们的不同发育阶段得到控制或者在它们的生产期间(例如,在研磨或者混合过程中,在它们的储藏或它们的使用过程中)更好的行为。
在这里,合适的活性成分的添加物是例如下面类别的活性成分的代表物:有机磷化合物、硝基苯酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍生物、脲类、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯类、新烟碱以及苏云金杆菌制剂。
以下具有化学式I的化合物与活性成分的混合物是优选的(缩写“TX”意为“选自下组的一种化合物,该组由描述于本发明的表1至88以及P中的化合物组成”):
佐剂,该佐剂选自由以下物质组成的组:石油(628)+TX,
杀螨剂,该杀螨剂选自由以下物质组成的组:1,1-双(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-1-萘乙酰胺(IUPAC名称)(1295)+TX、4-氯苯基苯基砜(IUPAC名称)(981)+TX、阿维菌素(1)+TX、灭螨醌(3)+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、α-氯氰菊酯(202)+TX、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、氨基硫代盐(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、益棉磷(44)+TX、保棉磷(azinphos-methyl)(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(azacyclotin)(46)+TX、偶氮磷(azothoate)(889)+TX、苯茵灵(62)+TX、苯诺沙磷(benoxafos)[CCN]+TX、苯螨特(benzoximate)(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、氟氯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯+TX、溴烯杀(bromocyclene)(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(bromopropylate)(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁酮威(butylpyridaben)+TX、石硫合剂(calciumpolysulfide)(IUPAC名称)(111)+TX、毒杀芬(campheechlor)(941)+TX、氯灭杀威(carbanolate)(943)+TX、甲萘威(115)+TX、克百威(carbofuran)(118)+TX、卡波硫磷(947)+TX、CGA 50’439(研究代码)(125)+TX、灭螨猛(chinomethionat)(126)+TX、杀螨醚(chlorbenside)(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、敌螨(968)+TX、杀螨酯(chlorfenson)(970)+TX、敌螨特(chlorfensulfide)(971)+TX、氯芬磷(131)+TX、乙酯杀螨醇(chlorobenzilate)(975)+TX、伊托明(chloromebuform)(977)+TX、灭虫脲(chloromethiuron)(978)+TX、丙酯杀螨醇(chloropropylate)(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(chlorthiophos)(994)+TX、瓜菊酯(cinerin)I(696)+TX、瓜菊酯11(696)+TX、瓜叶菊素(cinerins)(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺[CCN]+TX、库马磷(174)+TX、克罗米通[CCN]+TX、巴毒磷(crotoxyphos)(1010)+TX、硫杂灵(1013)+TX、果虫磷(cyanthoate)(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(demephion)(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(demeton)(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、甲基内吸磷-O(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、内吸磷-S-甲基磺隆(demeton-S-methylsulfon)(1039)+TX、杀螨隆(226)+TX、氯亚胺硫磷(dialifos)(1042)+TX、二嗪磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、甲氟磷(dicliphos)+TX、开乐散(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(dimefox)(1081)+TX、乐果(262)+TX、二甲杀螨霉素(dinacti)(653)+TX、消螨酚(dinex)(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(dinobuton)(269)+TX、敌螨普(dinocap)(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、二硝酯(1090)+TX、硝戊酯(dinopenton)(1092)+TX、硝辛酯(dinosulfon)(1097)+TX、硝丁酯(dinoterbon)(1098)+TX、敌恶磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双硫仑[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(dofenapyn)(1113)+TX、多拉克汀[CCN]+TX、硫丹(294)+TX、因毒磷(endothion)(1121)+TX、EPN(297)+TX、依立诺克丁[CCN]+TX、乙硫磷(309)+TX、益硫磷(ethoate-methyl)(1134)+TX、乙螨唑(etoxazole)(320)+TX、乙嘧硫磷(etrimfos)(1142)+TX、抗螨唑(fenazaflor)(1147)+TX、喹螨醚(328)+TX、苯丁锡(fenbutatin oxide)(330)+TX、苯硫威(fenothiocarb)(337)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)+TX、唑螨酯(fenpyroximate)(345)+TX、芬螨酯(fenson)(1157)+TX、氟硝二苯胺(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(fluacrypyrim)(360)+TX、氟佐隆(1166)+TX、氟螨噻(flubenzimine)(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(flucythrinate)(367)+TX、联氟螨(fluenetil)(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(flumethrin)(372)+TX、氟杀螨(fluorbenside)(1174)+TX、氟胺氰菊酯(fluvalinate)(1184)+TX、FMC 1137(研究代码)(1185)+TX、抗螨脒(405)+TX、抗螨脒盐酸盐(405)+TX、安硫磷(formothion)(1192)+TX、胺甲威(formparanate)(1193)+TX、γ-HCH(430)+TX、果绿啶(glyodin)(1205)+TX、苄螨醚(halfenprox)(424)+TX、庚烯醚(heptenophos)(432)+TX、十六碳烷基环丙烷羧酸酯(IUPAC/化学文摘名)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(isocarbophos)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸酯(IUPAC名称)(473)+TX、伊维菌素[CCN]+TX、茉莉菊酯(jasmolin)I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(jodfenphos)(1248)+TX、林丹(430)+TX、虱螨脲(490)+TX、马拉硫磷(492)+TX、苄丙二腈(malonoben)(1254)+TX、灭蚜磷(mecarbam)(502)+TX、地胺磷(mephosfolan)(1261)+TX、甲硫芬[CCN]+TX、虫螨畏(methacrifos)(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、溴甲烷(537)+TX、速灭威(metolcarb)(550)+TX、速灭磷(556)+TX、自克威(mexacarbate)(1290)+TX、米尔螨素(557)+TX、杀螨茵素肟(milbemycin oxime)[CCN]+TX、丙胺氟磷(mipafox)(1293)+TX、久效磷(561)+TX、茂硫磷(morphothion)(1300)+TX、莫昔克丁[CCN]+TX、二溴磷(naled)(567)+TX、NC-184(化合物代码)+TX、NC-152(化合物代码)+TX、氟蚊灵(nifluridide)(1309)+TX、尼柯霉素[CCN]+TX、戊氰威(nitrilacarb)(1313)+TX、戊氰威(nitrilacarb)1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧乐果(氧乐果)(594)+TX、杀线威(602)+TX、亚异砜磷(oxydeprofos)(1324)+TX、砜拌磷(oxydisulfoton)(1325)+TX、pp’-DDT(219)+TX、对硫磷(615)+TX、氯菊酯(626)+TX、石油(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX、硫环磷(phosfolan)(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、氯化松节油(polychloroterpenes)(传统名称)(1347)+TX、杀螨霉素(polynactins)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(promacyl)(1354)+TX、克螨特(671)+TX、胺丙畏(propetamphos)(673)+TX、残杀威(678)+TX、乙噻唑磷(prothidathion)(1360)+TX、发硫磷(prothoate)(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊素(pyrethrins)(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(pyridaphenthion)(701)+TX、嘧螨醚(pyrimidifen)(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、RA-17(研究代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(schradan)(1389)+TX、硫线磷(sebufos)+TX、塞拉菌素(selamectin)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(sophamide)(1402)+TX、季酮螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(研究代码)(1404)+TX、舒非仑[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、治螟磷(sulfotep)(753)+TX、硫黄(754)+TX、S21-121(研究代码)(757)+TX、氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(terbam)+TX、司替罗磷(777)+TX、三氯杀螨砜(tetradifon)(786)+TX、杀螨霉素(tetranactin)(653)+TX、杀螨硫醚(tetrasul)(1425)+TX、久效威(thiafenox)+TX、抗虫威(thiocarboxime)(1431)+TX、久效威(thiofanox)(800)+TX、甲基乙拌磷(thiometon)(801)+TX、克杀螨(1436)+TX、苏力菌素(thuringiensin)[CCN]+TX、威茵磷(triamiphos)(1441)+TX、苯噻螨(triarathene)(1443)+TX、三唑磷(820)+TX、唑呀威(triazuron)+TX、敌百虫(824)+TX、氯苯乙丙磷(trifenofos)(1455)+TX、甲杀螨霉素(trinactin)(653)+TX、灭蚜硫磷(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,该杀藻剂选自由以下物质组成的组:3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噁噻嗪-4-氧化物[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氢萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、茵多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯锡乙酸盐(IUPAC名称)(347)和氢氧化三苯锡(IUPAC名称)(347)+TX,
驱蠕虫剂,该驱蠕虫剂选自由以下物质组成的组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁[CCN]+TX、伊维菌素[CCN]+TX、米尔倍霉素[CCN]+TX、莫昔克丁[CCN]+TX、哌嗪[CCN]+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)和硫菌灵(thiophanate)(1435)+TX,
杀鸟剂,该杀鸟剂选自由以下物质组成的组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
杀细菌剂,该杀细菌剂选自由以下物质组成的组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双吡硫翁(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、二(二甲基二硫代氨基甲酸盐)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、烯丙苯噻唑(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX、和硫柳汞[CCN]+TX,
生物试剂,该生物试剂选自由以下物质构成的组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(12)+TX、放射形土壤杆菌(13)+TX、捕食螨(Amblyseius spp.)(19)+TX、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)(28)+TX、Anagrus atomus(29)+TX、短距蚜小蜂(Aphelinus abdominalis)(33)+TX、棉蚜寄生蜂(Aphidiuscolemani)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)(38)+TX、坚硬芽孢杆菌(Bacillus firmus)(48)+TX、球形芽孢杆菌(Bacillus sphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillusthuringiensis Berliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillusthuringiensis subsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵茵(Beauveria bassiana)(53)+TX、布氏白僵茵(Beauveria brongniartii)(54)+TX、草蜻蛉(Chrysoperla carnea)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(178)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)(191)+TX、西伯利亚离颚茧蜂(Dacnusasibirica)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(254)+TX、丽蚜小蜂(Encarsiaformosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(431)+TX、嗜茵异小杆线虫(Heterorhabditisbacteriophora)和H.megidis(433)+TX、会聚长足瓢虫(Hippodamia convergens)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(488)+TX、盲蝽(Macrolophuscaliginosus)(491)+TX、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(494)+TX、Metaphycus helvolus(522)+TX、黄绿绿僵茵(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)(学名)(523)+TX、松黄叶蜂(Neodiprion sertifer)核多角体病毒和红头松树叶蜂(N.lecontei)核多角体病毒(575)+TX、小花蝽(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(613)+TX、智利捕植螨(Phytoseiulus persimilis)(644)+TX、甜菜夜蛾(Spodopteraexigua multicapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernemabibionis)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(742)+TX、夜蛾斯氏线虫(742)+TX、Steinernema glaseri(742)+TX、Steinernema riobrave(另名)(742)+TX、Steinernema riobravis(742)+TX、Steinernema scapterisci(742)+TX、斯氏线虫属(Steinernema spp.)(742)+TX、赤眼蜂属(826)+TX、西方盲走螨(Typhlodromusoccidentalis)(844)和蜡蚧轮枝茵(Verticillium lecanii)(848)+TX,
土壤消毒剂,该土壤消毒剂选自由以下物质组成的组:碘甲烷(IUPAC名称)(542)和甲基溴(537)+TX,
化学不育剂,该化学不育剂选自由以下物质组成的组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)[CCN]+TX、白消安[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、不育特(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)[CCN]+TX、硫涕巴[CCN]+TX、曲他胺[CCN]和尿烷亚胺[CCN]+TX,
昆虫信息素,该昆虫信息素选自由以下物质组成的组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八-1-烯(IUPAC名称)(545)+TX、4-甲基壬醛-5-醇与4-甲基壬醛-5-酮(IUPAC名称)(544)+TX、α-多纹素(multistriatin)[CCN]+TX、西部松小蠹集合信息素(brevicomin)[CCN]+TX、十二碳二烯醇(codlelure)[CCN]+TX、十二碳二烯醇(codlemone)(167)+TX、诱蝇酮(cuelure)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、dominicalure[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚[CCN]+TX、南部松小蠹集合信息素(frontalin)[CCN]+TX、诱虫十六酯(gossyplure)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(421)+TX、诱杀烯混剂II(421)+TX、诱杀烯混剂III(421)+TX、诱杀烯混剂IV(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)[CCN]+TX、小蠢烯醇(ipsenol)[CCN]+TX、金龟子性诱剂(japonilure)(481)+TX、lineatin[CCN]+TX、litlure[CCN]+TX、粉纹夜蛾性诱剂(looplure)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid[CCN]+TX、诱虫醚(methyl eugenol)(540)+TX、诱虫烯(muscalure)(563)+TX、十八-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(orfralure)[CCN]+TX、oryctalure(317)+TX、非乐康(ostramone)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(736)+TX、食菌甲诱醇(sulcatol)[CCN]+TX、十四-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、特诱酮(839)+TX、特诱酮A(839)+TX、特诱酮B1(839)+TX、特诱酮B2(839)+TX、特诱酮C(839)和trunc-call[CCN]+TX,
昆虫驱避剂,该昆虫驱避剂选自以下物质组成的组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、避蚊胺[CCN]+TX、驱蚊酯(dimethyl carbate)[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、氨羰基甲酸酯(oxamate)[CCN]和羟哌酯[CCN]+TX,
杀昆虫剂,该杀昆虫剂选自由以下物质组成的组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-二(4-乙基苯基)乙烷(IUPAC名称)(1056)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、带有1,3-二氯丙烯的1,2-二氯丙烷(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、乙酸2,2,2-三氯-1-(3,4-二氯苯基)乙基酯(IUPAC名称)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯(IUPAC名称)(1066)+TX、二甲基氨基甲酸2-(1,3-二硫杂环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1109)+TX、硫氰酸2-(2-丁氧基乙氧基)乙基酯(IUPAC/化学文摘名称)(935)+TX、甲基氨基甲酸2-(4,5-二甲基-1,3-二氧环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇(IUPAC名称)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名称)(984)+TX、2-咪唑啉酮(IUPAC名称)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名称)(1246)+TX、甲基氨基甲酸2-甲基(丙-2-炔基)氨基苯基酯(IUPAC名称)(1284)+TX、月桂酸2-硫氰基乙基酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、二甲基氨基甲酸3-甲基-1-苯基吡唑-5-基酯(IUPAC名称)(1283)+TX、甲基氨基甲酸4-甲基(丙-2-炔基)氨基-3,5-二甲苯基酯(IUPAC名称)(1285)+TX、二甲基氨基甲酸5,5-二甲基-3-氧代环己-1-烯基酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、乙酰甲胺磷(2)+TX、啶虫脒(4)+TX、家蝇磷[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名称)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、氯甲桥萘(864)+TX、烯丙菊酯(17)+TX、阿洛氨菌素[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素[CCN]+TX、磷化铝(640)+TX、赛硫磷(870)+TX、硫代酰胺(872)+TX、灭害威(873)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、印楝素(41)+TX、甲基吡啶磷(42)+TX、谷硫磷-乙基(44)+TX、谷硫磷-甲基(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素类(52)+TX、六氟硅酸钡[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、Bayer 22/190(研究代码)(893)+TX、Bayer 22408(研究代码)(894)+TX、噁虫威(58)+TX、丙硫克百威(60)+TX、杀虫磺(66)+TX、β氟氯氰菊酯(194)+TX、β-氯氰菊酯(203)+TX、联苯菊酯(76)+TX、生物烯丙菊酯(78)+TX、生物烯丙菊酯S-环戊烯基异构体(79)+TX、戊环苄呋菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(908)+TX、除虫菊酯(80)+TX、二(2-氯乙基)醚(IUPAC名称)(909)+TX、双三氟虫脲(83)+TX、硼砂(86)+TX、溴灭菊酯+TX、溴苯烯磷(914)+TX、溴杀烯(918)+TX、溴-DDT[CCN]+TX、溴硫磷(920)+TX、溴硫磷-乙基(921)+TX、合杀威(924)+TX、噻嗪酮(99)+TX、畜虫威(926)+TX、脱甲基丁嘧啶磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯膦(932)+TX、丁酮砜威(104)+TX、丁基哒螨灵+TX、硫线磷(109)+TX、砷酸钙[CCN]+TX、氰化钙(444)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、甲萘威(115)+TX、克百威(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名称)(946)+TX、三硫磷(947)+TX、丁硫克百成(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、西伐丁(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、开蓬(963)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、定虫隆(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、三氯硝基甲烷(141)+TX、氯辛硫磷(989)+TX、灭虫吡啶(990)+TX、毒死蜱(145)+TX、毒死蜱-甲基(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、灰菊素I(696)+TX、灰菊素II(696)+TX、灰菊素类(696)+TX、顺式苄呋菊酯(cis-resmethrin)+TX、顺式苄呋菊酯(cismethrin)(80)+TX、功夫菊酯+TX、除线威(999)+TX、氯氰碘柳胺[CCN]+TX、噻虫胺(165)+TX、乙酰亚砷酸铜[CCN]+TX、砷酸铜[CCN]+TX、油酸铜[CCN]+TX、蝇毒磷(174)+TX、畜虫磷(1006)+TX、克罗米通[CCN]+TX、巴毒磷(1010)+TX、克芦磷酯(1011)+TX、冰晶石(177)+TX、CS 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25475(研究代码)(1386)+TX、尼亚那(ryania)(1387)+TX、利阿诺定(传统名称)(1387)+TX、沙巴藜芦(725)+TX、八甲磷(1389)+TX、硫线磷+TX、塞拉菌素[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN72129(研究代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(CCN)+TX、萨尔科福隆(sulcofuron)(746)+TX、萨尔科福隆钠(sulcofuron-sodium)(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油类(758)+TX、τ-氟胺氰菊酯(398)+TX、噻螨威(1412)+TX、TDE(1414)+TX、虫酰肼(762)+TX、吡螨胺(763)+TX、丁基嘧啶磷(764)+TX、氟苯脲(768)+TX、七氟菊酯(769)+TX、双硫磷(770)+TX、TEPP(1417)+TX、环戊烯丙菊酯(1418)+TX、叔丁威(terbam)+TX、特丁硫磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、四甲菊酯(787)+TX、θ氯氰菊酯(204)+TX、噻虫啉(791)+TX、塞芬诺克斯(thiafenox)+TX、噻虫嗪(792)+TX、苯噻硫磷(thicrofos)(1428)+TX、克虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢盐(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、虫线磷(1434)+TX、杀虫单(thiosultap)(803)+TX、杀虫双(thiosultap-sodium)(803)+TX、苏云金素[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反式苄氯菊酯(transpermethrin)(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威+TX、敌百虫(824)+TX、三氯偏磷酸-3(trichlormetaphos-3)[CCN]+TX、毒壤膦(1452)+TX、三氯丙氧磷(1455)+TX、杀铃脲(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭磷(847)+TX、甲烯氟虫腈(vaniliprole)[CCN]+TX、藜芦定(725)+TX、藜芦碱(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、ζ-氯氰菊酯(205)+TX、泽塔米林(zetamethrin)+TX、磷化锌(640)+TX、丙硫恶唑磷(zolaprofos)(1469)以及ZXI 8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫酰胺[500008-45-7]+TX、唑螨氰(cyenopyrafen)[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、氟虫吡喹(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素(spinetoram)[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶(sulfoxaflor)[946578-00-3]+TX、丁虫腈(flufiprole)[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX、triflumezopyrim(披露于WO 2012/092115中)+TX、fluxametamide(WO 2007/026965)+TX、ε-美特宁(epsilon-metofluthrin)[240494-71-7]+TX、ε-momfluorothrin[1065124-65-3]+TX、氟炔丙菊酯(fluazaindolizine)[1254304-22-7]+TX、氯炔丙菊酯(chloroprallethrin)[399572-87-3]+TX、fluxametamide[928783-29-3]+TX、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]+TX、tioxazafen[330459-31-9]+TX、双酰胺杀虫剂(broflanilide)[1207727-04-5]+TX、丁烯氟虫腈[704886-18-0]+TX、环溴虫酰胺[1031756-98-5]+TX、氟氰虫酰胺(tetraniliprole)[1229654-66-3]+TX、戊吡虫胍(描述在WO 2010/060231中)+TX、环氧虫啶(描述在WO 2005/077934中)+TX,
杀软体动物剂,该杀软体动物剂选自由以下物质组成的组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺乙醇胺盐(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、杀螺吗啉(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、乙酸三苯基锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、皮瑞普(pyriprole)[394730-71-3]+TX,
杀线虫剂,该杀线虫剂选自由以下物质组成的组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名)(1065)+TX、3-(4-氯苯基)-5-甲基绕丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(210)+TX、阿巴美丁(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(aldoxycarb)(863)+TX、AZ 60541(化合物代码)+TX、benclothiaz[CCN]+TX、苯茵灵(62)+TX、丁基哒螨酮(butylpyridaben)+TX、硫线磷(cadusafos)(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(141)+TX、毒死蜱(145)+TX、除线威(cloethocarb)(999)+TX、细胞分裂素(cytokinins)(210)+TX、棉隆(216)+TX、DBCP(1045)+TX、DCIP(218)+TX、除线特(diamidafos)(1044)+TX、除线磷(dichlofenthion)(1051)+TX、二克磷(dicliphos)+TX、乐果(262)+TX、依马克丁[CCN]+TX、苯甲酸依马克丁(291)+TX、依立诺克丁(291)+TX、[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛[CCN]+TX、GY-81(研究代码)(423)+TX、速杀硫磷(heterophos)[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、isamidofos(1230)+TX、氯唑磷(isazofos)(1231)+TX、激动素(kinetin)[CCN]+TX、糠氨基嘌呤(mecarphon)(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(519)+TX、威百亩钠盐(519)+TX、甲基溴(537)+TX、异硫氰酸甲酯(543)+TX、杀螨菌素肟(milbemycin oxime)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑茵(Myrothecium verrucaria)组分(565)+TX、NC-184(化合物代码)+TX、杀线威(602)+TX、甲拌磷(636)+TX、磷胺(639)+TX、磷虫威(phosphocarb)[CCN]+TX、硫线磷(sebufos)+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiaf enox+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(210)+TX、fluensulfone[318290-98-1]+TX,
硝化作用抑制剂,该硝化作用抑制剂选自由以下物质组成的组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
植物激活剂,该植物激活剂选自由以下物质组成的组:噻二唑素(acibenzolar)(6)+TX、噻二唑素-S-甲基(6)+TX、烯丙苯噻唑(probenazole)(658)和大虎杖(Reynoutriasachalinensis)提取物(720)+TX,
杀鼠剂,该杀鼠剂选自由以下物质组成的组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氮醛糖(127)+TX、氯鼠酮(140)+TX、维生素D3(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠钠(273)+TX、维生素D2(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、鼠朴定(1183)+TX、盐酸鼠朴定(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氢氰酸(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、甲基溴(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX,
增效剂,该增效剂选自由以下物质组成的组:2-(2-丁氧基乙氧基)乙基胡椒基酯(IUPAC名称)(934)+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮(IUPAC名称)(903)+TX、具有橙花叔醇的法呢醇(324)+TX、MB-599(研究代码)(498)+TX、MGK 264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,该动物驱避剂选自由以下物质组成的组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍盐(guazatine)(422)+TX、双胍醋酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
杀病毒剂,该杀病毒剂选自由以下物质组成的组:衣马宁[CCN]和利巴韦林[CCN]+TX,
创伤保护剂,该创伤保护剂选自由以下物质组成的组:氧化汞(512)+TX、辛噻酮(590)和甲基硫茵灵(802)+TX,
以及生物活性化合物,这些化合物选自由以下物质组成的组:阿扎康唑[60207-31-0]+TX、联苯三唑醇[70585-36-3]+TX、糠菌唑[116255-48-2]+TX、环唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、稻瘟酯[101903-30-4]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟(pyrifenox)[88283-41-4]+TX、丙氯灵[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidine)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、恶霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、甲菌利(myclozoline)[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、氟酰胺(Flutolanil)[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离碱)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、烯肟菌酯{Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX、氟嘧菌酯[361377-29-9]+TX、甲基醚菌酯[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲代森锌(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、苯氟磺胺[1085-98-9]+TX、唑啶草(fluoroimide)[41205-21-4]+TX、灭菌丹[133-07-3]+TX、甲苯氟磺胺[731-27-1]+TX、波尔多(bordeaux)混合物[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、氯化铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[131-72-6]+TX、酞菌酯(硝基thal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、克菌磷(pyrazophos)[13457-18-6]+TX、甲基托氯磷(tolclofos-methyl)[57018-04-9]+TX、苯并噻二唑(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYP LI90(Flumorph)[211867-47-9]+TX、二噻农(dithianon)[3347-22-6]+TX、噻唑菌胺(ethaboxam)[162650-77-3]+TX、土菌灵(etridiazole)[2593-15-9]+TX、恶唑菌酮[131807-57-3]+TX、咪唑菌酮(fenamidone)[161326-34-7]+TX、稻瘟酰胺(Fenoxanil)[115852-48-7]+TX、三苯锡(fentin)[668-34-8]+TX、嘧菌腙(ferimzone)[89269-64-7]+TX、氟啶胺(fluazinam)[79622-59-6]+TX、氟吡菌胺(fluopicolide)[239110-15-7]+TX、磺菌胺(flusulfamide)[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、福赛得(fosetyl-aluminium)[39148-24-8]+TX、恶霉灵(hymexazol)[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF 916(赛座灭(Cyazofamid))[120116-88-3]+TX、春雷霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+TX、戊菌隆(pencycuron)[66063-05-6]+TX、苯酞[27355-22-2]+TX、多氧霉素(polyoxins)[11113-80-7]+TX、噻菌灵(probenazole)[27605-76-1]+TX、百维威(propamocarb)[25606-41-1]+TX、碘喹唑酮(proquinazid)[189278-12-4]+TX、乐喹酮(pyroquilon)[57369-32-1]+TX、喹氧灵[124495-18-7]+TX、五氯硝苯[82-68-8]+TX、硫[7704-34-9]+TX、噻酰菌胺[223580-51-6]+TX、咪唑嗪(triazoxide)[72459-58-6]+TX、三环唑[41814-78-2]+TX、嗪氨灵[26644-46-2]+TX、有效霉素[37248-47-8]+TX、苯酰菌胺(zoxamide)(RH7281)[156052-68-5]+TX、双炔酰菌胺(mandipropamid)[374726-62-2]+TX、吡蚜酮(isopyrazam)[881685-58-1]+TX、塞德因(sedaxane)[874967-67-6]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO2007/048556中)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(3’,4’,5’-三氟-联苯基-2-基)-酰胺(披露于WO 2006/087343中)+TX、[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]甲基-环丙甲酸酯[915972-17-7]+TX以及1,3,5-三甲基-N-(2-甲基-1-氧丙基)-N-[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H-吡唑-4-甲酰胺[926914-55-8]+TX;以及
微生物剂,包括:鲁氏不动杆菌+TX、交替枝顶孢(Acremonium alternatum)+TX+TX、顶头孢霉(Acremonium cephalosporium)+TX+TX、Acremonium diospyri+TX、Acremonium obclavatum+TX、棉褐带卷蛾颗粒体病毒(AdoxGV)+TX、放射形土壤杆菌菌株K84 +TX、互隔链格孢+TX、决明链格孢(Alternaria cassia)+TX、损毁链格孢+TX、白粉寄生孢+TX、黄曲霉AF36+TX、黄曲霉NRRL 21882+TX、曲霉属+TX、出芽短梗霉+TX、固氮螺菌属+TX、(+TX、TAZO)+TX、固氮菌属+TX、圆褐固氮菌+TX、孢囊固氮菌(Bionatural Blooming)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、原生祛病芽孢杆菌(Bacillus chitinosporus)菌株CM-1+TX、原生祛病芽孢杆菌菌株AQ746+TX、地衣芽孢杆菌菌株HB-2(BiostartTM )+TX、地衣芽孢杆菌菌株3086(+TX、Green)+TX、环状芽孢杆菌+TX、坚硬芽孢杆菌(+TX、+TX、)+TX、坚硬芽孢杆菌菌株I-1582+TX、浸麻芽孢杆菌+TX、Bacillusmarismortui+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、日本甲虫芽孢杆菌(Milky Spore)+TX、短小芽孢杆菌属+TX、短小芽孢杆菌菌株GB34(Yield)+TX、短小芽孢杆菌菌株AQ717+TX、短小芽孢杆菌菌株QST 2808(+TX、Ballad)+TX、球形芽孢杆菌+TX、芽孢杆菌属+TX、芽孢杆菌属菌株AQ175+TX、芽孢杆菌属菌株AQ177+TX、芽孢杆菌属菌株AQ178+TX、枯草芽孢杆菌菌株QST 713(+TX、+TX、)+TX、枯草芽孢杆菌菌株QST 714+TX、枯草芽孢杆菌菌株AQ153+TX、枯草芽孢杆菌菌株AQ743+TX、枯草芽孢杆菌菌株QST3002+TX、枯草芽孢杆菌菌株QST3004+TX、枯草芽孢杆菌解淀粉变种菌株FZB24(+TX、)+TX、苏云金芽孢杆菌Cry2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis aizawai)GC 91+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis israelensis)(+TX、+TX、)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)(+TX、+TX、+TX、+TX、Scutella+TX、Turilav+TX、+TX、Dipel+TX、+TX、)+TX、苏云金芽孢杆菌库尔斯塔克亚种BMP 123+TX、苏云金芽孢杆菌库尔斯塔克亚种HD-1+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌鲇泽变种(+TX、)+TX、细菌属(+TX、+TX、)+TX、密执安棍状杆菌(Clavipacter michiganensis)的噬菌体+TX、+TX、球孢白僵菌(+TX、Brocaril)+TX、球孢白僵菌GHA(Mycotrol+TX、Mycotrol+TX、)+TX、布氏白僵菌(+TX、Schweizer+TX、)+TX、白僵菌属+TX、灰葡萄孢霉+TX、大豆慢生型根瘤菌+TX、短短小芽孢杆菌+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis tenebrionis)+TX、BtBooster+TX、洋葱伯克霍尔德菌(+TX、+TX、Blue)+TX、伯克霍尔德菌(Burkholderia gladii)+TX、唐菖蒲伯克霍尔德菌+TX、伯克霍尔德菌属+TX、加拿大蓟真菌(CBH Canadian)+TX、奶酪假丝酵母+TX、无名假丝酵母+TX、Candidafructus+TX、光滑念珠菌+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母+TX、橄榄假丝酵母菌株O+TX、近平滑假丝酵母+TX、菌膜假丝酵母+TX、铁红假丝酵母+TX、拉考夫假丝酵母(Candida reukaufii)+TX、齐藤假丝酵母(Candida saitoana)(+TX、)+TX、清酒假丝酵母+TX、假丝酵母属+TX、纤细假丝酵母+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌+TX、螺卷毛壳+TX、球毛壳菌+TX、铁杉紫色杆菌(Chromobacterium subtsugae)菌株PRAA4-1T+TX、枝状枝孢菌+TX、尖孢枝孢+TX、Cladosporium chlorocephalum+TX、枝孢属+TX、极细枝孢霉+TX、粉红粘帚霉+TX、尖孢炭疽菌(Colletotrichumacutatum)+TX、盾壳霉(Cotans)+TX、盾壳霉属+TX、浅白隐球酵母+TX、土生隐球菌+TX、Cryptococcus infirmo-miniatus+TX、罗伦隐球酵母+TX、苹果异形小卷蛾颗粒体病毒+TX、坎平贪铜菌(Cupriavidus campinensis)+TX、苹果蠹蛾颗粒体病毒+TX、苹果蠹蛾颗粒体病毒(+TX、Madex+TX、MadexMax/)+TX、Cylindrobasidium laeve+TX、枝双孢霉属+TX、汉逊德巴利酵母+TX、Drechslera hawaiinensis+TX、阴沟肠杆菌+TX、肠杆菌科+TX、毒力虫霉+TX、黑附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球菌属+TX、花状线黑粉菌(Filobasidium floriforme)+TX、锐顶镰孢菌+TX、厚垣镰孢霉+TX、尖镰孢(/Biofox)+TX、层生镰孢+TX、镰孢属+TX、溶磷白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(+TX、)+TX、粉红粘帚霉+TX、粘帚霉属+TX、绿色粘帚霉+TX、颗粒体病毒属+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、沿岸盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属+TX、冰下盐单胞菌(Halomonas subglaciescola)+TX、盐弧菌变型(Halovibriovariabilis)+TX、葡萄汁有孢汉逊酵母+TX、棉铃虫核型多角体病毒+TX、玉米穗虫核型多角体病毒+TX、异黄酮-芒柄花黄素+TX、柠檬克勒克酵母+TX、克勒克酵母属+TX、大链壶菌(Lagenidium giganteum)+TX、长孢蜡蚧菌(Lecanicillium longisporum)+TX、蜡蚧轮枝菌(Lecanicilliummuscarium)+TX、舞毒蛾核多角体病毒+TX、嗜盐海球菌+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌+TX、绿僵菌(Destruxin)+TX、Metschnikowia fruticola+TX、美极梅奇酵母(Metschnikowiapulcherrima)+TX、Microdochium dimerum+TX、蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、Muscodor albus 620+TX、Muscodor roseus菌株A3-5+TX、菌根属(Mycorrhizae spp.)(+TX、Root)+TX、疣孢漆斑菌菌株AARC-0255+TX、BROS+TX、Ophiostoma piliferum菌株D97+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(+TX、)+TX、淡紫拟青霉(Paecilomyces linacinus)(Biostat)+TX、淡紫拟青霉菌株251(MeloCon)+TX、多粘类芽孢杆菌+TX、成团泛菌(BlightBan)+TX、泛菌属+TX、巴斯德氏芽菌属+TX、Pasteuria nishizawae+TX、黄灰青霉+TX、Penicillium billai(+TX、)+TX、短密青霉+TX、常现青霉+TX、灰黄青霉+TX、产紫青霉+TX、青霉菌属+TX、纯绿色肯霉+TX、大伏革菌(Phlebiopsis gigantean)+TX、解磷细菌+TX、隐地疫霉+TX、棕榈疫霉+TX、异常毕赤酵母+TX、Pichia guilermondii+TX、膜醭毕赤氏酵母+TX、指甲毕赤酵母+TX、树干毕赤酵母+TX、铜绿假单胞菌+TX、致金色假单胞菌(Pseudomonas aureofasciens)(Spot-Less)+TX、洋葱假单胞菌+TX、绿针假单胞菌+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌菌株A506(BlightBan)+TX、恶臭假单胞菌+TX、Pseudomonas reactans+TX、假单胞菌属+TX、丁香假单胞菌+TX、绿黄假单胞菌+TX、荧光假单胞菌+TX、Pseudozyma flocculosa菌株PF-A22UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Puccinia thlaspeos(Wood)+TX、侧雄腐霉菌(Pythium paroecandrum)+TX、寡雄腐霉(+TX、)+TX、缠器腐霉+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩菌属+TX、根瘤菌(+TX、)+TX、丝核菌属+TX、球状红球菌菌株AQ719+TX、双倒卵形红冬孢酵母菌(Rhodosporidium diobovatum)+TX、圆红冬孢酵母菌+TX、红酵母属+TX、粘红酵母+TX、禾本红酵母+TX、胶红酵母(Rhodotorula mucilagnosa)+TX、深红酵母+TX、酿酒酵母+TX、玫瑰色盐水球菌(Salinococcus roseus)+TX、小核盘菌+TX、小核盘菌+TX、柱顶孢霉属+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(+TX、)+TX、粘质沙雷氏菌+TX、普城沙雷菌+TX、沙雷氏菌属+TX、粪生粪壳菌+TX、海灰翅夜蛾核型多角体病毒+TX、红掷孢酵母+TX、嗜麦芽寡养单胞菌+TX、不吸水链霉菌+TX、白丘链霉菌(Streptomyces albaduncus)+TX、脱叶链霉菌+TX、鲜黄链霉菌+TX、灰平链霉菌+TX、灰绿链霉菌+TX、利迪链霉菌+TX、利迪链霉菌WYEC-108+TX、紫色链霉菌+TX、小铁艾酵母(Tilletiopsis minor)+TX、铁艾酵母属+TX、棘孢木霉(T34)+TX、盖姆斯木霉(Trichoderma gamsii)+TX、深绿木霉+TX、钩状木霉TH 382+TX、里法哈茨木霉(Trichoderma harzianum rifai)+TX、哈茨木霉T-22(+TX、PlantShield+TX、+TX、)+TX、哈茨木霉T-39+TX、非钩木霉(Trichoderma inhamatum)+TX、康宁木霉+TX、木霉属LC 52+TX、木素木霉+TX、长柄木霉+TX、多孢木霉(Trichoderma polysporum)(Binab)+TX、紫杉木霉+TX、绿色木霉+TX、绿色木霉(原来称为绿色粘帚霉GL-21)+TX、绿色木霉+TX、绿色木霉菌株ICC 080+TX、茁芽丝孢酵母+TX、毛孢子菌属+TX、单端孢属+TX、粉红单端孢+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细基格孢+TX、奥德曼细基格孢(Ulocladiumoudemansii)+TX、玉蜀黍黑粉菌+TX、各种细菌和补充营养素(Natural)+TX、各种真菌(Millennium)+TX、厚垣轮枝孢菌+TX、蜡蚧轮枝菌(+TX、)+TX、Vip3Aa20+TX、Virgibaclillus marismortui+TX、野油菜黄单胞菌(Xanthomonas campestris pv.Poae)+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;以及
植物提取物,包括:松油+TX、印楝素(Plasma Neem+TX、+TX、+TX、+TX、植物IGR(+TX、)+TX、菜籽油(Lilly Miller)+TX、土荆芥附近荆芥(Chenopodium ambrosioidesnear ambrosioides)+TX、菊花浓汁(Chrysanthemum extract)+TX、提取印楝油(extract of neem oil)+TX、唇形科的精油+TX、丁香迷迭香薄荷的提取物和百里香精油(Garden insect)+TX、甜菜碱+TX、大蒜+TX、柠檬草精油+TX、印度楝树精油+TX、猫薄荷(薄荷精油)+TX、荆芥卡塔琳娜州(Nepeta catarina)+TX、尼古丁+Tx、牛至精油+TX、胡麻科精油+TX、除虫菊+TX、皂皮树+TX、大虎杖(Reynoutria sachalinensis)(+TX、)+TX、鱼藤酮(Eco)+TX、芸香料植物提取物+TX、豆油(Ortho)+TX、茶树精油(Timorex)+TX、百里香精油+TX、MMF+TX、+TX、迷迭香芝麻薄荷百里香和肉桂提取物的混合物(EF)+TX、丁香迷迭香和薄荷提取物的混合物(EF)+TX、丁香薄荷大蒜油和薄菏的混合物(Soil)+TX、高岭土+TX、储存葡萄糖的褐藻以及
信息素,包括:黑头萤火虫信息素(3M喷洒型黑头萤火虫)+TX、苹果蠹蛾信息素(派拉蒙分配器(Paramount dispenser)-(CM)/Isomate)+TX、葡萄卷叶蛾信息素(3M MEC-GBM喷洒型 )+TX、卷叶虫信息素(3M MEC-LR喷洒型)+TX、家蝇信息素(Snip7Fly+TX、Starbar Premium Fly)+TX、梨小食心虫信息素(3M梨小食心虫喷洒型)+TX、桃树钻心虫信息素 +TX、番茄蛲虫信息素(3M喷洒型)+TX、Entostat粉(来自棕榈树的提取物)(Exosex)+TX、(E+TX、Z+TX、Z)-3+TX、8+TX、11十四烷三烯基乙酸酯+TX、(Z+TX、Z+TX、E)-7+TX、11+TX、13-十六碳三烯醛+TX、(E+TX,Z)-7+TX、9-十二碳二烯-1-基乙酸酯+TX、2-甲基-1-丁醇+TX、乙酸钙+TX、+TX、+TX、+TX、薰衣草千里酸酯;以及
宏生物剂,包括:短距蚜小蜂+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、Acerophagus papaya+TX、二星瓢虫 +TX、二星瓢虫+TX、二星瓢虫+TX、串茧跳小蜂(Ageniaspiscitricola)+TX、巢蛾多胚跳小蜂+TX、安氏钝绥螨(Amblyseius andersoni)(+TX、)+TX、加州钝绥螨(Amblyseius californicus)(+TX、)+TX、胡瓜钝绥螨(+TX、Bugline)+TX、伪钝绥螨+TX、斯氏钝绥螨(Bugline+TX、)+TX、奥氏钝绥螨+TX、粉虱细蜂(Amitus hesperidum)+TX、原缨翅缨小蜂(Anagrusatomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyruskamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)+TX、短距蚜小蜂(+TX、)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、科列马·阿布拉小蜂(Aphidius colemani)+TX、阿尔蚜茧蜂+TX、烟蚜茧蜂+TX、桃赤蚜蚜茧蜂+TX、食蚜瘿蚊+TX、食蚜瘿蚊+TX、岭南蚜小蜂+TX、印巴黄金蚜小蜂+TX、蠊卵长尾啮小蜂(Aprostocetus hagenowii)+TX、隐翅虫(Atheta coriaria)+TX、熊蜂属+TX、欧洲熊蜂(Natupol)+TX、欧洲熊蜂(+TX、)+TX、Cephalonomia stephanoderis+TX、黑背红瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)+TX、普通草蛉+TX、红通草蛉(Chrysoperla rufilabris)+TX、Cirrospilus ingenuus+TX、Cirrospilus quadristriatus+TX、白星橘啮小蜂(Citrostichus phyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerus属+TX、Coccidoxenoides perminutus+TX、Coccophagus cowperi+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂+TX、菜蛾盘绒茧蜂+TX、孟氏隐唇瓢虫(+TX、)+TX、日本方头甲+TX、西伯利亚离颚茧蜂+TX、西伯利亚离颚茧蜂+TX、豌豆潜蝇姬小蜂+TX、小黑瓢虫(Delphastus catalinae)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂+TX、Diaparsisjucunda+TX、阿里食虱跳小蜂(Diaphorencyrtus aligarhensis)+TX、豌豆潜叶蝇姬小蜂+TX、豌豆潜叶蝇姬小蜂(+TX、)+TX、西伯利亚离颚茧蜂(+TX、)+TX、歧脉跳小蜂属+TX、盾蚧长缨蚜小蜂+TX、丽蚜小蜂(Encarsia+TX、+TX、)+TX、浆角蚜小蜂(Eretmoceruseremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇+TX、Eretmoceris siphonini+TX、浆角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(+TX、Eretline)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、海氏桨角蚜小蜂+TX、蒙氏桨角蚜小蜂(+TX、Eretline)+TX、Eretmocerussiphonini+TX、四斑光缘瓢虫(Exochomus quadripustulatus)+TX、食螨瘿蚊(Feltiellaacarisuga)+TX、食螨瘿蚊+TX、阿里山潜蝇茧蜂+TX、Fopiusceratitivorus+TX、芒柄花黄素(Wirless)+TX、细腰凶蓟马+TX、西方静走螨(Galendromus occidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂+TX、异色瓢虫+TX、异小杆线虫属(Lawn)+TX、嗜菌异小杆线虫(NemaShield+TX、+TX、+TX、+TX、+TX、+TX、+TX、)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys+TX、BioNem+TX、Exhibitline+TX、)+TX、集栖瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspisaculeifer)(+TX、)+TX、兵下盾螨(Hypoaspismiles)(Hypoline+TX、)+TX、黑色枝跗瘿蜂+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色丽突跳小蜂(Leptomastidea abnormis)+TX、Leptomastix dactylopii+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇+TX、茶足柄瘤蚜茧蜂+TX、暗黑长脊盲蝽(Macrolophus caliginosus)(+TX、 +TX、)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycus lounsburyi+TX、角纹脉褐蛉+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni+TX、Neodryinustyphlocybae+TX、加州新小绥螨+TX、胡瓜钝绥螨+TX、虚伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇+TX、狡小花蝽(Oriusinsidiosus)(+TX、Oriline)+TX、无毛小花蝽(Oriuslaevigatus)(+TX、Oriline)+TX、大型小花蝽(Oriusmajusculus)(Oriline)+TX、小黑花椿象+TX、Pauesiajuniperorum+TX、酸酱瓢虫腹柄姬小蜂(Pediobius foveolatus)+TX、Phasmarhabditis hermaphrodita+TX、Phymastichus coffea+TX、Phytoseiulus macropilus+TX、智利小植绥螨(+TX、 )+TX、斑腹刺益蝽+TX、Pseudacteon curvatus+TX、Pseudacteon obtusus+TX、Pseudacteontricuspis+TX、Pseudaphycusmaculipennis+TX、Pseudleptomastix mexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttalia concolor)(complex)+TX、胯姬小蜂属+TX、Rhyzobius lophanthae+TX、澳洲瓢虫+TX、Ruminadecollate+TX、Semielacher petiolatus+TX、麦长管蚜+TX、小卷蛾斯氏线虫(Nematac+TX、+TX、BioNem+TX、+TX、+TX、)+TX、夜蛾斯氏线虫(+TX、Nemasys+TX、BioNem+TX、+TX、+TX、+TX、Exhibitline+TX、+TX、)+TX、锯蜂线虫(Steinernema kraussei)(Nemasys+TX、BioNem+TX、Exhibitline)+TX、里奥布拉夫线虫(Steinernema riobrave)(+TX、)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(Nematac)+TX、斯氏线虫属+TX、Steinernematid属(Guardian)+TX、深点食螨瓢虫+TX、亮腹釉小蜂+TX、Tetrastichus setifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Tricholine)+TX、甘蓝夜蛾赤眼蜂 +TX、广赤眼蜂+TX、微小赤眼蜂+TX、玉米螟赤眼蜂+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂+TX、螟黑点瘤姬蜂;以及
其他生物剂,包括:脱落酸+TX、+TX、银叶菌(Chondrostereumpurpureum)(Chontrol)+TX、盘长孢状刺盘孢+TX、辛酸铜盐+TX、δ陷阱(Delta trap)(Trapline)+TX、解淀粉欧文氏菌(Harpin)(+TX、Ni-HIBIT Gold)+TX、磷酸高铁+TX、漏斗陷阱(Trapline)+TX、+TX、Grower's+TX、高油菜素内酯+TX、磷酸铁(LillyMiller Worry Free Ferramol Slug&Snail)+TX、MCP冰雹陷阱(Trapline)+TX、Microctonus hyperodae+TX、Mycoleptodiscus terrestris+TX、+TX、+TX、+TX、信息素陷阱(Thripline)+TX、碳酸氢钾+TX、脂肪酸的钾盐+TX、硅酸钾溶液 +TX、碘化钾+硫氰酸钾+TX、+TX、蜘蛛毒+TX、蝗虫微孢子虫(Semaspore OrganicGrasshopper)+TX、粘着陷阱(Trapline+TX、Rebell)+TX以及陷阱(Takitrapline y+)+TX。
在活性成分之后的括号中的参考例如[3878-19-1]是指化学文摘登记号。以上描述的混合配伍物是已知的。当活性成分包括在“杀有害生物剂手册(The PesticideManual)”[杀有害生物剂手册-一本世界手册(The Pesticide Manual-A WorldCompendium);第十三版;编者:C.D.S.汤姆林(TomLin);英国农作物保护委员会(TheBritish Crop Protection Council)]中时,它们在上文对于特定化合物在圆括号内给定的条目编号之下描述于该手册中;例如,化合物“阿巴美丁”在条目编号(1)之下进行了描述。当以上对特定化合物加入“[CCN]”时,所讨论的化合物包括在“杀有害生物剂通用名纲要(Compendium of Pesticide Common Names)”中,该纲要在互联网上可得:[A.伍德(Wood);杀有害生物剂通用名纲要(Compendium of Pesticide Common Names),版权1995-2004];例如,化合物“乙酰虫腈”在互联网地址http://www.alanwood.net/pesticides/acetoprole.html下进行了描述。
上述的活性成分中大部分在上文是通过所谓的“通用名”、相关的“ISO通用名”或在个别情况下使用的另一个“通用名”来提及。如果名称不是“通用名”,那么所用名称的性质实际上指定在特定化合物的圆括号中;在那种情况下,使用IUPAC名称、IUPAC/化学文摘名称、“化学名称”、“传统名称”、“化合物名称”或“开发代码”。“CAS登记号”意指化学文摘登记号。
选自表1至88以及P的具有化学式I的化合物与上述活性成分的活性成分混合物包括选自表1至88以及P的化合物和上述活性成分,优选地是处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其从10:1至1:10,非常尤其是从5:1和1:5,尤其优选的是从2:1至1:2的比率给出的,并且从4:1至2:1的比率同样是优选的,特别是处于1:1,或5:1,或5:2,或5:3,或5:4,或4:1,或4:2,或4:3,或3:1,或3:2,或2:1,或1:5,或2:5,或3:5,或4:5,或1:4,或2:4,或3:4,或1:3,或2:3,或1:2,或1:600,或1:300,或1:150,或1:35,或2:35,或4:35,或1:75,或2:75,或4:75,或1:6000,或1:3000,或1:1500,或1:350,或2:350,或4:350,或1:750,或2:750,或4:750的比率。那些混合比率是按重量计的。
如上描述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上描述的混合物的组合物施用于有害生物或其环境中,除了通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法之外。
包含选自表1至88以及P的具有化学式I的化合物以及一种或多种如上所述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷洒混合物(该混合物由这些单一活性成分的单独配制品构成)(例如“桶混制剂”)施用,并且当以一种顺序的方式(即,一个在另一个适度短的时期之后,例如几小时或几天)施用时组合使用这些单独活性成分来施用。施用选自表1至88以及P的这些具有化学式I的化合物和如上所述活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物I的用途也是本发明的主题。
这些组合物的施用方法,即是控制上述类型的有害生物的方法,如喷雾、雾化,撒粉,刷涂,包衣,撒播或浇灌-它们被选择以适于普遍情况的预期目的-并且这些组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1ppm与1000ppm之间,优选地在0.1ppm与500ppm之间的活性成分。每公项的施用量总体上是每公项1g到2000g活性成分,尤其是10g/ha到1000g/ha,优选地10g/ha到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,该活性成分可以通过根系统(内吸作用)到达植物,这是通过用液体组合物将这些植物的所在地浸透或者通过将固体形式的活性成分引入植物的所在地(例如引入土壤,例如以颗粒(土施)的形式)来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量地添加淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物)对抗上述类型的有害生物。可以用该化合物在种植前对该繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过施涂固体组合物层实现的。当该繁殖材料被种植在施用处时,还可能例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于待控制的植物和有害生物/真菌,并且通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,如在每100kg种子10克至100克之间。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在优选实施例中是指真正的种子。
本发明还包括用具有化学式I的化合物包衣或处理的种子或含有具有化学式I的化合物的种子。术语“包衣或处理和/或含有”通常表示在施用的时候,在大多数情况下,活性成分在种子的表面,尽管成分的更多或更少的部分可以渗透到种子材料中,这取决于施用的方法。当所述种子产品被(再)种植时,它可以吸收活性成分。在一个实施例中,本发明使得其上粘附有具有化学式(I)的化合物的植物繁殖材料可得。此外,由此可得包括用具有化学式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法实现具有化学式(I)的化合物的种子处理施用,如在种子播种之前或播种/种植过程中喷雾或通过撒粉。
生物学实例:
实例B1:烟粉虱(棉粉虱):摄食/接触活性
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用成年粉虱进行侵染。孵育6天之后,针对死亡率对这些样品进行检查。以下化合物在200ppm施用率下得到至少80%的死亡率:P9、P13和P14。
实例B2:黄瓜条叶甲(玉米根虫)
将24孔微量滴定板中的置于琼脂层上的玉米芽用通过喷雾用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(6至10只/孔)。侵染4天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P1、P2、P3、P4、P5、P6、P7、P8、P9、P10、P11、P12、P13、P14以及P15。
实例B3:英雄美洲蝽(新热带区褐蝽象)
将24孔微量滴定板中的琼脂上的大豆叶片用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,用N2期若虫对叶片进行侵染。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。以下化合物在200ppm施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P1、P3、P8、P9、P10、P13、P14和P15
实例B4:桃蚜(绿色桃蚜虫):摄食/接触活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的蚜虫群体进行侵染。侵染6天之后,针对死亡率对这些样品进行评估。以下化合物在200ppm施用率下得到至少80%的死亡率:P10、P13、P14和P15。
实例B5:桃蚜(绿色桃蚜虫)。系统活性
将受到混合年龄的蚜虫群体侵染的豌豆幼苗的根部直接放在从10'000ppm DMSO储备溶液中制备的水性测试溶液中。将幼苗放置在测试溶液中6天之后,针对死亡率对这些样品进行评估。以下化合物在24ppm测试速率下得到至少80%的死亡率:P10。
实例B6:小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))
将具有人工饲料的24孔微量滴定板用从10’000ppm DMSO储备溶液中制备的水性测试溶液通过移液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(10至15只/孔)。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P1、P2、P3、P4、P6、P8、P9、P10、P11、P12、P13、P14以及P15。
实例B7:海灰翅夜蛾(埃及棉叶虫)
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用五只L1期幼虫进行侵染。侵染3天之后,相比于未处理样品,针对死亡率、拒食效果以及生长抑制对这些样品进行评估。当类别(死亡率、拒食效果、以及生长抑制)中至少一个高于未处理样品时,测试样品对海灰翅夜蛾给出了控制。以下化合物在200ppm施用率下得到至少80%的控制:P1、P2、P3、P4、P5、P6、P8、P9、P10、P11、P12、P13、P14以及P15。
实例B8:海灰翅夜蛾(埃及棉叶虫)系统活性
将测试化合物用移液管从10’000ppm DMSO储备溶液施用到24孔板中并且与琼脂进行混合。将莴苣种子置于琼脂上并且用另一块也包含琼脂的平板封闭该多孔板。7天之后,根吸收了化合物并且莴苣生长进入了盖平板。然后,将这些莴苣叶切到盖平板中。将夜蛾属卵吸移穿过潮湿凝胶印记纸上的塑料模板及其所封闭的盖平板。侵染6天之后,相比于未处理样品,针对死亡率、拒食效果以及生长抑制对这些样品进行评估。以下化合物在12.5ppm测试比率下给出了三个类别(死亡率、拒食效果、或生长抑制)中至少一个的至少80%的效果:
P10、P13、P14和P15。
实例B9:二点叶螨(二斑叶螨):摄食/接触活性
将24孔微量滴定板中的琼脂上的豆叶圆片用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的螨种群进行侵染。侵染8天之后,针对混合种群(流动平台)的死亡率对这些样品进行评估。以下化合物在200ppm施用率下得到至少80%的死亡率:P10和P13。
实例B10:烟蓟马(葱蓟马)摄食/接触活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的蓟马种群进行侵染。侵染6天之后,针对死亡率对这些样品进行评估。以下化合物在200ppm施用率下得到至少80%的死亡率:P3和P10。
实例B11:埃及伊蚊(黄热病蚊子):
在乙醇中,以200ppm的施用率,将测试溶液施加到12孔组织培养皿中。一旦沉积物干燥,将五天、两天至五天大的成年雌性埃及伊蚊添加到每个孔中,并且在棉塞中保持10%的蔗糖溶液。引入后一小时,进行击倒评估,并且在引入后24小时和48小时,评估死亡率。以下化合物在48h和/或24h后对埃及伊蚊给出至少80%的控制::P9、P10、P11、P13、P14和P15。
实例B12:斯氏按蚊(印度疟蚊):
在乙醇中,以200ppm的施用率,将测试溶液施用到12孔组织培养皿中。一旦沉积物干燥,将五天、两天至五天大的成年雌性斯氏按蚊添加到每个孔中,并且在棉塞中保持10%的蔗糖溶液。引入后一小时,进行击倒评估,并且在引入后24小时和48小时,评估死亡率。以下化合物在48h和/或24h后对斯氏按蚊给出至少80%的控制:P10和P13。
对比实例:
现有技术化合物:在WO 2015/000715的第196页中描述的化合物V12.03:
本发明的化合物:
化合物V12.03、P1和P3在结构上是相同的,除了吡啶部分的取代模式。现有技术化合物V12.03的吡啶部分是未取代的,本发明的化合物P1和P3在吡啶环的6-位置处分别被吡唑和苯基基团取代。将该吡唑基团用三氟甲基取代,并且苯基基团用氯取代。
实例B13:
对黄瓜条叶甲(玉米根虫)、小菜蛾(Plutella xylostella)(小菜蛾(Diamondblack moth))和海灰翅夜蛾(埃及棉叶虫)的杀虫作用。分别如生物学实例B2、B6和B7所述进行试验,其中幼虫摄食/接触活性报告为转折点(Breakpoint)(BP80)值(百万分之几)(即给出80%的幼虫死亡率的最低浓度)。
表B13:对黄瓜条叶甲(玉米根虫)、小菜蛾(Plutella xylostella)(小菜蛾
(Diamond black moth))和海灰翅夜蛾(埃及棉叶虫)的杀虫作用。
从表B13可以看出,与现有技术的化合物V12.03相比,根据本发明的化合物P1和P3对黄瓜条叶甲(玉米根虫)、小菜蛾(Plutella xylostella)(小菜蛾(Diamond blackmoth))和海灰翅夜蛾(埃及棉叶虫)显示出优异的杀虫作用。
鉴于这些化合物的结构相似性,所以杀虫活性的这种出人意料的增强不是可预期的。
实例B14:本发明的化合物与现有技术化合物的杀虫活性的比较:
为了证明与现有技术相比出人意料的杀虫活性的增加,已经测试了以下化合物的杀虫活性:
现有技术化合物:在WO 2015/000715的第196页中描述的化合物V12.01:
本发明的化合物:
化合物V12.01、P4和P5在结构上是相同的,除了吡啶部分的取代模式。现有技术化合物V12.03的吡啶部分在6-位置处是未取代的,本发明的化合物P1和P3在吡啶部分的6-位置处被一个苯基部分取代。该苯基部分分别在3-和4-位置处被三氟甲基取代。在所有这三种化合物中,吡啶部分的5-位置被三氟甲基取代。
实例B14:
对黄瓜条叶甲(玉米根虫)的杀虫作用。如生物学实例B6所述进行试验,其中幼虫喂养/接触活性被报告为转折点(BP80)值(百万分之几)(即给出80%的幼虫死亡率的最低浓度)。
表B14:对黄瓜条叶甲(玉米根虫)的杀虫作用。
表B14:杀虫作用
从表B14可以看出,与现有技术的化合物V12.01相比,根据本发明的化合物P4和P5对黄瓜条叶甲(玉米根虫)显示出优异的杀虫作用。
鉴于这些化合物的结构相似性,所以杀虫活性的这种出人意料的增强不是可预期的。
Claims (13)
1.一种具有化学式I的化合物,
其中
A表示CH、N或N-氧化物;
A1是CH、N或N-氧化物;
Q是可以被选自下组的取代基单取代或多取代的苯基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是五-元至十元单环的或稠合的双环的环系统,该环系统经由碳原子连接至包含基团A的环,所述环系统可以是芳香族的、部分饱和的或完全饱和的并且包含1至4个选自下组的杂原子,该组由以下各项组成:氮、氧和硫,其条件是每个环系统不能包含多于2个氧原子和多于2个硫原子,所述五-元至十元环系统可以被独立地选自下组的取代基单-取代至多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是部分饱和的或完全饱和的五元至六元芳香族环系统,该环系统经由氮原子连接至包含基团A的环,所述环系统可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;并且所述环系统包含1个、2个或3个选自下组的杂原子,该组由以下各项组成:氮、氧和硫,其条件是所述环系统不能包含多于一个氧原子和多于一个硫原子;或者
Q是C3-C6环烷基,或被选自下组的取代基单取代或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、CONH2、羧基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C2-C6烯基,或被选自下组的取代基单取代或多取代的C2-C6烯基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C2-C6炔基,或被选自下组的取代基单取代或多取代的C2-C6炔基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、三(C1-C4烷基)甲硅烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代-烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
Q是C1-C6烷基,或被选自下组的取代基单取代或多取代的C1-C6烷基,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、三(C1-C4烷基)甲硅烷基和苯基,其中所述苯基可以被选自下组的取代基单取代或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代-烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基;或者
R1是被选自下组的取代基单取代或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;或
R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2是卤素、氰基、C1-C6卤代烷基或被一个或两个选自下组的取代基取代的C1-C6卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;或者
R2是C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、O(C1-C4卤代烷基)、或-C(O)C1-C4卤代烷基;或者
R2是可以被选自下组的取代基单取代或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;
X1是NR5,其中R5是氢、C1-C4烷基、C2-C6烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基;或者
X1是氧或硫;
R3是氢或C1-C2-烷基;
R4是氢、卤素或C1-C3卤代烷基;
以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体。
2.根据权利要求1所述的具有化学式I的化合物,其中
Q选自下组,该组由以下杂环基团组成:
吡咯基;吡唑基;异噁唑基;呋喃基(furanyl);噻吩基;咪唑基;噁唑基;噻唑基;异噻唑基;三唑基;噁二唑基;噻二唑基;四唑基;呋喃基(furyl);吡啶基;嘧啶基;吡嗪基;哒嗪基;三嗪基,吡喃基;喹唑啉基;异喹啉基;吲嗪基;异苯并呋喃基萘啶基;喹喔啉基;噌啉基;酞嗪基;苯并噻唑基;苯并噁唑基;苯并三唑基;吲唑基;吲哚基;(1H-吡咯-1-基)-;(1H-吡咯-2-基)-;(1H-吡咯-3-基)-;(1H-吡唑-1-基)-;(1H-吡唑-3-基)-;(3H-吡唑-3-基)-;(1H-吡唑-4-基)-;(3-异噁唑基)-;(5-异噁唑基)-;(2-呋喃基)-;(3-呋喃基)-;(2-噻吩基)-;(3-噻吩基)-;(1H-咪唑-2-基)-;(1H-咪唑-4-基)-;(1H-咪唑-5-基)-;(2-噁唑-2-基)-;(噁唑-4-基)-;(噁唑-5-基)-;(噻唑-2-基)-;(噻唑-4-基)-;(噻唑-5-基)-;(异噻唑-3-基)-;(异噻唑-5-基)-;(1H-1,2,3-三唑-1-基)-;(1H-1,2,4-三唑-3-基)-;(4H-1,2,4-三唑-4-基)-;(1H-1,2,4-三唑-1-基)-;(1,2,3-噁二唑-2-基)-;(1,2,4-噁二唑-3-基)-;(1,2,4-噁二唑-4-基)-;(1,2,4-噁二唑-5-基)-;(1,2,3-噻二唑-2-基)-;(1,2,4-噻二唑-3-基)-;(1,2,4-噻二唑-4-基)-;(1,3,4-噻二唑-5-基)-;(1H-四唑-1-基)-;(1H-四唑-5-基)-;(2H-四唑-5-基)-;(2-吡啶基)-;(3-吡啶基)-;(4-吡啶基)-;(2-嘧啶基)-;(4-嘧啶基)-;(5-嘧啶基)-;(2-吡嗪基)-;(3-哒嗪基)-;(4-哒嗪基)-;(1,3,5-三嗪-2-基)-;(1,2,4-三嗪-5-基)-;(1,2,4-三嗪-6-基)-;(1,2,4-三嗪-3-基)-;(呋咱-3-基)-;(2-喹啉基)-;(3-喹啉基)-;(4-喹啉基)-;(5-喹啉基)-;(6-喹啉基)-;(3-异喹啉基)-;(4-异喹啉基)-;(2-喹唑啉基)-;(2-喹喔啉基)-;(5-喹喔啉基)-;(吡啶并[2,3-b]吡嗪-7-基)-;(苯并噁唑-5-基)-;(苯并噻唑-5-基)-;(苯并[b]噻吩-2-基)-和(苯并[1,2,5]噁二唑-5-基)-;二氢吲哚基以及四氢喹啉基。
6.根据权利要求4所述的具有化学式I-1的化合物,由具有化学式I-1a的化合物表示
其中
A是N或CH;
X是S或SO2;
R1是C1-C4烷基;
R2是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
R4是氢或C1-C2卤代烷基;
Qa1选自下组,该组由以下取代基组成
其中每个Rx独立地选自下组,该组由以下各项组成:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
8.根据权利要求5所述的具有化学式I-2的化合物,由具有化学式I-2a的化合物表示
A是N或CH;
X是S或SO2;
R1是C1-C4烷基
R2是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
R4是氢或C1-C1-C2卤代烷基;
Qa1优选地选自下组,该组由以下取代基组成
其中每个Rx独立地选自:氢、卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
10.根据权利要求1所述的具有化学式I的化合物,其中
R1是C1-C4烷基;
R2是C1-C4卤代烷基或C1-C4卤代烷基硫烷基;
R3是氢;
R4是氢或C1-C4卤代烷基;
Q是苯基,该苯基可以被选自下组的取代基单取代、二取代或三取代,该组由以下各项组成:卤素和C1-C4卤代烷基;或者
Q是C2-C6烯基,该C2-C6烯基可以被苯基单取代,该苯基本身可以被C1-C4卤代烷基单取代;或者
Q是吡唑基,该吡唑基可以被C1-C4卤代烷基或卤素单取代;或者
Q是嘧啶基或C3-C6环烷基,所述环烷基可以被氰基取代;或者
Q是三唑基,该三唑基可以被卤素取代;或者
Q是C1-C4烷基,该C1-C4烷基可以被氰基取代;或者
Q是C2-C6炔基,该C2-C6炔基可以被苯基单取代,该苯基本身可以被卤素单取代或二取代;
X是S或SO2;
X1是N-C1-C4烷基;特别是N-CH3;
A是CH或N;并且
A1是CH或N。
11.一种杀有害生物组合物,该杀有害生物组合物包含至少一种根据权利要求1所述的具有化学式I的化合物或适当时其互变异构体作为活性成分以及至少一种助剂,该化合物在所有情况下为游离形式或农用化学上可用的盐形式。
12.一种用于控制有害生物的方法,该方法包括将根据权利要求11所述的组合物施用于这些有害生物或其环境中,除了通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法之外。
13.一种用于保护种子免受有害生物攻击的方法,该方法包括用根据权利要求11所述的组合物处理这些种子或这些种子所种植的场所。
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BR112017015514A2 (pt) | 2018-05-02 |
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CN107207501A (zh) | 2017-09-26 |
JP6949712B2 (ja) | 2021-10-13 |
US20170362224A1 (en) | 2017-12-21 |
US10981907B2 (en) | 2021-04-20 |
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