CN112638893A - 作为抗菌剂的取代的噻吩甲酰胺及类似物 - Google Patents
作为抗菌剂的取代的噻吩甲酰胺及类似物 Download PDFInfo
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- CN112638893A CN112638893A CN201980056124.2A CN201980056124A CN112638893A CN 112638893 A CN112638893 A CN 112638893A CN 201980056124 A CN201980056124 A CN 201980056124A CN 112638893 A CN112638893 A CN 112638893A
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- 239000003242 anti bacterial agent Substances 0.000 title description 3
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 title description 2
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 234
- 238000000034 method Methods 0.000 claims description 121
- 239000000203 mixture Substances 0.000 claims description 54
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 235000013399 edible fruits Nutrition 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- JAARIXSMRWKNFX-UHFFFAOYSA-N 4,5-dibromo-3-fluorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1F JAARIXSMRWKNFX-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- QEZRPOCNDKTQJO-UHFFFAOYSA-N 3,4,5-tribromothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1Br QEZRPOCNDKTQJO-UHFFFAOYSA-N 0.000 claims description 3
- XOUIIPXNMPQGGQ-UHFFFAOYSA-N 4,5-dibromo-3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Br)=C(Br)C=1Cl XOUIIPXNMPQGGQ-UHFFFAOYSA-N 0.000 claims description 3
- KUXNSSLEHIUORH-UHFFFAOYSA-N 4,5-dibromo-3-methylthiophene-2-carboxylic acid Chemical compound CC=1C(Br)=C(Br)SC=1C(O)=O KUXNSSLEHIUORH-UHFFFAOYSA-N 0.000 claims description 3
- XZOTWSGVXFPSJX-UHFFFAOYSA-N 4,5-dichloro-3-methylthiophene-2-carboxylic acid Chemical compound CC=1C(Cl)=C(Cl)SC=1C(O)=O XZOTWSGVXFPSJX-UHFFFAOYSA-N 0.000 claims description 3
- PJVUDYYMBPNSCN-UHFFFAOYSA-N FC1=C(SC(=C1Cl)Cl)C(=O)O Chemical compound FC1=C(SC(=C1Cl)Cl)C(=O)O PJVUDYYMBPNSCN-UHFFFAOYSA-N 0.000 claims description 3
- GKKNVRTWKLFMGM-UHFFFAOYSA-N ethyl 3,4,5-tribromothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(Br)C=1Br GKKNVRTWKLFMGM-UHFFFAOYSA-N 0.000 claims description 3
- LSBUOEYCPAQAHW-UHFFFAOYSA-N ethyl 4,5-dibromo-3-chlorothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(Br)C=1Cl LSBUOEYCPAQAHW-UHFFFAOYSA-N 0.000 claims description 3
- PMPBGORMHXRHRT-UHFFFAOYSA-N ethyl 5-amino-4-bromo-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(N)=C(Br)C=1C PMPBGORMHXRHRT-UHFFFAOYSA-N 0.000 claims description 3
- DKJRFAFPCROFRG-UHFFFAOYSA-N methyl 3,4,5-tribromothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1Br DKJRFAFPCROFRG-UHFFFAOYSA-N 0.000 claims description 3
- RJQBWMPIDVDQQA-UHFFFAOYSA-N methyl 4,5-dibromo-3-chlorothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1Cl RJQBWMPIDVDQQA-UHFFFAOYSA-N 0.000 claims description 3
- CUZHIRPKCADYDJ-UHFFFAOYSA-N methyl 4,5-dibromo-3-fluorothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1F CUZHIRPKCADYDJ-UHFFFAOYSA-N 0.000 claims description 3
- WQCQDITXZPVXGB-UHFFFAOYSA-N methyl 4,5-dibromo-3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=C(Br)C=1C WQCQDITXZPVXGB-UHFFFAOYSA-N 0.000 claims description 3
- ONBHJNHOAHJNOU-UHFFFAOYSA-N methyl 4,5-dichloro-3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Cl)=C(Cl)C=1C ONBHJNHOAHJNOU-UHFFFAOYSA-N 0.000 claims description 3
- GCUKJYDLGIHDNA-UHFFFAOYSA-N tert-butyl 3,4,5-tribromothiophene-2-carboxylate Chemical compound CC(C)(C)OC(=O)C=1SC(Br)=C(Br)C=1Br GCUKJYDLGIHDNA-UHFFFAOYSA-N 0.000 claims description 3
- 238000007080 aromatic substitution reaction Methods 0.000 claims description 2
- ZALICZHDGFSEES-UHFFFAOYSA-N ethyl 4-amino-3,5-dibromothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(N)C=1Br ZALICZHDGFSEES-UHFFFAOYSA-N 0.000 claims description 2
- YKAGQTREVLIQQP-UHFFFAOYSA-N 4,5-dibromo-3-iodothiophene-2-carboxylic acid Chemical compound BrC=1C(=C(SC=1Br)C(=O)O)I YKAGQTREVLIQQP-UHFFFAOYSA-N 0.000 claims 1
- ZJSJAOJZNUPFAT-UHFFFAOYSA-N BrC=1C(=C(SC=1Br)C(=O)OCC)F Chemical compound BrC=1C(=C(SC=1Br)C(=O)OCC)F ZJSJAOJZNUPFAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- NDYGRQGMBKZQEO-UHFFFAOYSA-N ethyl 4,5-dibromo-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(Br)=C(Br)C=1C NDYGRQGMBKZQEO-UHFFFAOYSA-N 0.000 claims 1
- KSIQQGMITDVMPW-UHFFFAOYSA-N methyl 4,5-dichloro-3-fluorothiophene-2-carboxylate Chemical compound ClC=1C(=C(SC=1Cl)C(=O)OC)F KSIQQGMITDVMPW-UHFFFAOYSA-N 0.000 claims 1
- -1 thienyl oxazolones Chemical class 0.000 abstract description 147
- 241000894006 Bacteria Species 0.000 abstract description 22
- 241000589634 Xanthomonas Species 0.000 abstract description 11
- 241000196324 Embryophyta Species 0.000 description 153
- 239000000460 chlorine Substances 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000002253 acid Substances 0.000 description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000005566 Imazamox Substances 0.000 description 16
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 241000894120 Trichoderma atroviride Species 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 241000193388 Bacillus thuringiensis Species 0.000 description 12
- 239000005531 Flufenacet Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 244000063299 Bacillus subtilis Species 0.000 description 11
- 235000014469 Bacillus subtilis Nutrition 0.000 description 11
- 230000001580 bacterial effect Effects 0.000 description 11
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 11
- 239000000417 fungicide Substances 0.000 description 11
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000010353 genetic engineering Methods 0.000 description 10
- 230000000670 limiting effect Effects 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- 241000589636 Xanthomonas campestris Species 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
- 229940097012 bacillus thuringiensis Drugs 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 230000001276 controlling effect Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 241000219198 Brassica Species 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000233866 Fungi Species 0.000 description 8
- 241000223260 Trichoderma harzianum Species 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 241000894007 species Species 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 230000009466 transformation Effects 0.000 description 8
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 8
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- QEGVVEOAVNHRAA-UHFFFAOYSA-N 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)sulfanylbenzoic acid Chemical compound COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C(O)=O)=N1 QEGVVEOAVNHRAA-UHFFFAOYSA-N 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
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- 239000005857 Trifloxystrobin Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000002068 genetic effect Effects 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- 125000004269 oxiran-2-yl group Chemical group [H]C1([H])OC1([H])* 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 6
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 6
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical class [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 6
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 6
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 239000012973 diazabicyclooctane Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 6
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- 239000004149 tartrazine Substances 0.000 description 1
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- 229960000943 tartrazine Drugs 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
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- 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
- URHWNXDZOULUHC-UHFFFAOYSA-N tert-butyl n-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]carbamate Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(NC(=O)OC(C)(C)C)=N1 URHWNXDZOULUHC-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
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- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
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- 230000014616 translation Effects 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-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
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
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- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- XPHOBMULWMGEBA-VZFHVOOUSA-N valienamine Chemical compound N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O XPHOBMULWMGEBA-VZFHVOOUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
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- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
Abstract
本公开内容涉及式(III)的噻吩基噁唑酮及其类似物,其可用于保护植物免受细菌性病害,尤其是由属于黄单胞菌属的细菌所引起的细菌性病害。
Description
技术领域
本发明涉及噻吩基噁唑酮及其类似物,其可用于保护植物免于细菌性病害,尤其是由属于黄单胞菌属的细菌引起的细菌性病害。
背景技术
植物病原性细菌可在全世界范围内造成严重的经济破坏性病害。在植物病原性细菌中,属于黄单胞菌属的细菌被认为是最具破坏性的。它们是具有农艺学意义的不同宿主植物上的各种病害的致病原因。这类病害的实例包括:影响辣椒和番茄的细菌性斑点病(由野油菜黄单胞菌疱病致病变种(Xanthomonas campestris pv.vesicatoria)所引起);影响所有经培育的芸苔属(例如,抱子甘蓝(Brussels sprout)、卷心菜、花椰菜和西兰花)的十字花科植物的黑腐病(由野油菜黄单胞菌野油菜致病变种(Xanthomonas campestrispv.campestris)所引起);影响柑橘属种(酸橙、柑橘、葡萄柚、柚子)的柑橘溃疡病(由地毯草黄单胞菌柑桔致病变种(Xanthomonas axonopodis pv.citri)所引起);影响稻的细菌性叶枯病(由水稻黄单胞菌水稻致病变种(Xanthomonas oryzae pv.oryzae)所引起);影响李属属种(例如,杏、李子、桃)的叶斑病(由树生黄单胞菌桃李致病变种(Xanthomonasarboricola pv.pruni)所引起);影响豆类的常见细菌性枯萎病(由菜豆黄单胞菌(Xanthomonas phaseoli)所引起);影响木薯的木薯细菌性枯萎病(由地毯草黄单胞菌木薯萎蔫致病变种(Xanthomonas axonopodis pv.manihotis)所引起)以及影响棉花的角斑病/细菌性枯萎病(由野油菜黄单胞菌锦葵致病变种(Xanthomonas campestrispv.malvacearum)所引起)。
可以不同方式来防治细菌性植物病害,主要包括使用抗病害植物品种以及使用杀菌剂(天然的或合成的)。医学中的耐抗生素危机以及一些耐抗生素植物病原体的出现引发了抗生素替代品的研发,以保持其功效并扩大病害管理解决方案的范围。因此,已研发出不直接作用于病原性细菌(即不具有直接的抗生素作用)但刺激植物自身的防御系统的产品。这些产品称为植物防御激活剂。植物防御激活剂的实例包括:阿拉酸式苯-S-甲基(acibenzolar-S-methyl)(以和市售)、2,6-二氯异烟酸、β-氨基丁酸、烯丙苯噻唑(probenazole)水杨酸、核黄素、调环酸钙(prohexadione-calcium)、膦酸钾、超敏蛋白(harpin protein)和茉莉酸甲酯。
尽管许多不同的有机和无机化合物已表现出可激活植物的诱导抗性,但目前只有很少的产品在市场上销售。
因此,仍需要提供新的化学品和方法,其可在低剂量下有效地防治细菌性病害,尤其是由属于黄单胞菌属的细菌所引起的病害,同时不与细菌直接相互作用,从而防止抗性发展。由于化学品不与细菌直接相互作用,它们不太可能对这些化学品产生抗性。
本发明人已证明,属于噻吩基噁唑酮类的新的化学品提供了上述问题的解决方案。
已知一些噻吩基噁唑酮用于对抗植物病害。例如,WO 2004/062361公开了据称可有效防治真菌性病害的化合物。它们通过直接作用于不需要的微生物而发挥作用,但也会对植物产生抗性诱导效应。WO2004/062361还表明这些化合物可用于防治细菌性病害,但没有提供这类活性的任何证据。本发明的发明人发现了这些化合物在低剂量下对野油菜黄单胞菌野油菜致病变种具有差的效果。
发明内容
本发明涉及如权利要求所述的式(III)的化合物,以及其制备方法及用于其制备的中间体。
本发明还涉及如本文所述的一种防治细菌性病害的方法。
具体实施方式
已发现,下文所示的式(III)的化合物在低剂量(即,低至31ppm的剂量)下有效地防治了由黄单胞菌属的细菌所引起的病害,同时不显示出直接的杀菌作用。
因此,本发明涉及式(III)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基。
本文中不涵盖由与自然法则相悖以及本领域技术人员基于他/她的专业知识将因此排除的组合所得到的化合物。例如,排除具有三个或更多个相邻氧原子的环结构。
根据取代基的性质,式(III)的化合物可以不同立体异构体的形式存在。这些立体异构体为例如对映体、非对映体、阻转异构体或几何异构体。因此,本发明涵盖纯的立体异构体和这些异构体的任何混合物。当化合物可以平衡状态的两种以上的互变异构体形式存在时,借助于一种互变异构描述提及的化合物应被视为包括所有互变异构体形式。
根据化合物中双键的数量,本发明的任意化合物还可以一种或多种几何异构体的形式存在。根据关于双键或环的取代基的性质,几何异构体可以顺式(=Z-)或反式(=E-)形式存在。因此,本发明同样涉及所有的几何异构体以及所有比例的所有可能的混合物。
式(III)的化合物可适当地为其游离形式、盐形式、N-氧化物形式或溶剂合物形式(例如,水合物)。
根据取代基的性质,式(III)的化合物可以游离化合物和/或其盐(如农业化学上的活性盐)的形式存在。
农业化学上的活性盐包括无机酸和有机酸的酸加成盐以及常规碱的盐。无机酸的实例为氢卤酸(如氢氟酸、氢氯酸、氢溴酸和氢碘酸)、硫酸、磷酸和硝酸,以及酸式盐(如硫酸氢钠和硫酸氢钾)。有用的有机酸包括,例如,甲酸、碳酸和烷酸(如乙酸、三氟乙酸、三氯乙酸和丙酸),以及乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、具有6至20个碳原子的饱和或单不饱和或二不饱和的脂肪酸、烷基硫酸单酯、烷基磺酸(具有碳原子为1至20个的直链或支链烷基基团的磺酸)、芳基磺酸或芳基二磺酸(带有一个或两个磺酸基团的芳族基团,如苯基和萘基)、烷基膦酸(具有碳原子为1至20个的直链或支链烷基基团的膦酸)、芳基膦酸或芳基二膦酸(带有一个或两个膦酸基团的芳族基团,如苯基和萘基),其中烷基和芳基基团可带有其他取代基,例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
式(III)的化合物或其盐的溶剂合物为化合物与溶剂的化学计量组合物。
式(III)的化合物可以多种结晶和/或无定形形式存在。结晶形式包括未溶剂化的结晶形式、溶剂合物和水合物。
在一些实施方案中,本发明涉及式(III)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子或甲基。
在一些实施方案中,本发明的化合物为如上文所公开的式(III)的化合物,其中R3与R1和R2不同。
本发明涉及表III.1中所公开的任何化合物。
式(III)的化合物可用于防治细菌性病害,尤其用于防治由属于黄单胞菌属的细菌所引起的病害。
制备式(III)的化合物的方法
本发明涉及制备式(III)的化合物的方法。式(III)的化合物可通过类似于已知方法(参见本文的参考)的各种路径制备,以及通过下文和实验部分中所描述的一种或多种以下合成路径来制备。
除非另有说明,在下文中,R1、R2和R3具有如上文针对式(III)的化合物所给出的相同含义。
方法A3
本文所定义的式(III)的化合物可通过方法A3由其中R4为氢原子的式(XXI)的化合物或其一种盐经环化反应来制备,如以下反应方案所示:
方法A3
方法A3可根据Journal of Heterocyclic Chemistry,25(1),209-215;1988;WO2007003536中的描述来进行。
用于进行方法A3的合适路易斯酸可为常用于这些反应的无机路易斯酸和有机路易斯酸。优选使用金属卤化物,如氯化铝(III)、氯化铁(III)、氯化锌(II)、四氯化钛、三氟化硼;三氟甲磺酸盐,如三氟甲磺酸钪(III)、三氟甲磺酸铋(III)或三氟甲磺酸镱(III),以及碘。
用于进行方法A3的合适布朗斯特酸可为常用于这些反应的无机布朗斯特酸和有机布朗斯特酸。优选使用卤化氢,如氯化氢或溴化氢;磺酸,如对甲苯磺酸、樟脑磺酸、甲磺酸或三氟甲磺酸以及多磷酸、磷酸、硫酸、亚硫酸氢钾、三氟乙酸或乙酸。
用于进行方法A3的其他合适的缩合剂可在以下物质组成的非限制性列表中选择:酰卤形成剂,如光气、三溴化磷、三氯化磷、五氯化磷、三氯氧磷、草酰氯或亚硫酰氯;酸酐形成剂,如氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;酸酐,如三氟乙酸酐或乙酸酐;碳二亚胺,如N,N'-二环己基碳二亚胺(DCC)、N-(3-二甲基氨基丙基)-N'-乙基碳二亚胺盐酸盐(EDC)或其他常用缩合剂,如五氧化二磷、多磷酸、双(2-氧代-3-噁唑烷基)次磷酰氯、1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸盐(HATU)、2-(1H-苯并三唑-1-基)-1,1,3,3-四甲基脲四氟硼酸盐(TBTU)、(1-氰基-2-乙氧基-2-氧代亚乙基氨基氧基)二甲基氨基-吗啉基-碳鎓六氟磷酸盐、N,N'-羰基-二咪唑、2-乙氧基-N-乙氧基羰基-1,2-二氢喹啉(EEDQ)、三苯基膦/四氯甲烷、4-(4,6-二甲氧基[1.3.5]-三嗪-2-基)-4-甲基吗啉鎓氯化物水合物、双(2-氧代-3-噁唑烷基)次磷酰氯(BOP-Cl)、三吡咯烷基溴化鏻六氟磷酸盐(PyBroP)、2-氯-1,3-二甲基咪唑鎓氯化物(DMC)或丙烷膦酸酐(T3P)。
用于进行本发明方法A3的合适缚酸剂在各种情况下为常用于这些反应的所有无机碱和有机碱。优选碱金属碳酸盐,如碳酸铯、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠;碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙;以及叔胺,如三甲胺、三乙胺、二异丙基乙胺、三丁胺、N,N-二甲基苯胺、N-甲基哌啶、N,N-二甲基吡啶-4-胺、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU);或芳族碱,如吡啶。
用于进行方法A3的合适溶剂无特别限制。它们可为常用的惰性有机溶剂,只要其不溶解化合物以与其反应或表现出与其有任何特定的相互作用即可。优选使用任选卤代的脂族、脂环族或芳族烃,如石油醚、戊烷、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯、十氢萘、ISOPARTM E或ISOPARTM G;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、2-甲基四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正丁腈或异丁腈或苯甲腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;脲,如1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮;酯,如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜;或砜,如环丁砜;及其混合物。
方法A3可在惰性气氛下进行。当进行方法A3时,每摩尔式(XXI)的化合物可采用0.01至5摩尔%的合适的酸或缩合剂,且每摩尔式(XXI)的化合物可采用0.01至5摩尔的缚酸剂。还可使用以其他比例的反应组分。后处理通过已知方法进行。
式(XXI)的化合物(其中R4表示氢原子)可通过熟知方法(如碱性水解)由式(XXI)的化合物(其中R4表示C1-C6-烷基)来制备。
制备式(XXI)的化合物-方法PXXI(1)
式(XXI)的化合物(其中R4为氢原子或C1-C6-烷基)可通过包括以下步骤的方法PXXI(1)来制备:使式(XXII)的化合物与式(XXIII)的化合物或其一种盐反应,如以下反应方案所示:
方法PXXI(1)
其中R4为氢原子或C1-C6-烷基,且U1为卤素原子、羟基或C1-C6-烷氧基。
当U1表示羟基时,本发明的方法PXXI(1)有利地在缩合剂的存在下进行。合适的缩合剂可在由以下物质组成的非限制性列表中选择:酰卤形成剂,如光气、三溴化磷、三氯化磷、五氯化磷、三氯氧磷、草酰氯或亚硫酰氯;酸酐形成剂,如氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;碳二亚胺,如N,N'-二环己基碳二亚胺(DCC)、N-(3-二甲基氨基丙基)-N'-乙基碳二亚胺盐酸盐(EDC)或其他常用缩合剂,如五氧化二磷、多磷酸、双(2-氧代-3-噁唑烷基)次磷酰氯、1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸盐(HATU)、2-(1H-苯并三唑-1-基)-1,1,3,3-四甲基脲四氟硼酸盐(TBTU)、(1-氰基-2-乙氧基-2-氧代亚乙基氨基氧基)二甲基氨基-吗啉基-碳鎓六氟磷酸盐、N,N'-羰基-二咪唑、2-乙氧基-N-乙氧基羰基-1,2-二氢喹啉(EEDQ)、三苯基膦/四氯甲烷、4-(4,6-二甲氧基[1.3.5]-三嗪-2-基)-4-甲基吗啉鎓氯化物水合物、双(2-氧代-3-噁唑烷基)次磷酰氯(BOP-Cl)、三吡咯烷基溴化鏻六氟磷酸盐(PyBroP)、2-氯-1,3-二甲基咪唑鎓氯化物(DMC)或丙烷膦酸酐(T3P)。
当U1表示卤素原子时,本发明的方法PXXI(1)有利地在缚酸剂的存在下进行。用于进行本发明的方法PXXI(1)的合适缚酸剂在每种情况下为常用于这些反应的所有无机碱和有机碱。优选碱金属碳酸盐,如碳酸铯、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠;碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙;以及叔胺,如三甲胺、三乙胺、二异丙基乙胺、三丁胺、N,N-二甲基苯胺、N-甲基哌啶、N,N-二甲基吡啶-4-胺、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU);或芳族碱,如吡啶。
当U1表示C1-C6-烷氧基时,本发明的方法PXXI(1)可任选地在路易斯酸如三甲基铝的存在下用过量的胺组分进行。
如果合适,方法PXXI(1)可在碱的存在下并且如果合适在溶剂的存在下,优选在无水条件下进行。
用于进行方法PXXI(1)的合适的溶剂无特别限制。它们可为常用的惰性有机溶剂,只要其不溶解化合物以与其反应或表现出与其有任何特定的相互作用即可。优选使用任选卤代的脂族、脂环族或芳族烃,如石油醚、戊烷、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯、十氢萘、ISOPARTM E或ISOPARTM G;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、2-甲基四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正丁腈或异丁腈或苯甲腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;脲,如1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮;酯,如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜;或砜,如环丁砜;及其混合物。
方法PXXI(1)可在惰性气氛如氩气或氮气气氛中进行。当进行方法PXXI(1)时,每摩尔式XXIII的化合物可使用1摩尔或过量的式XXIII的化合物和1至5摩尔的碱。还可使用以其他比例的反应组分。后处理通过已知方法进行。
式(XXIII)的化合物为市售可得的,或可通过熟知的方法制备。
其中U1表示羟基的式(XXII)的化合物为市售可得的,其可由其中U1表示C1-C6-烷氧基的式(XXII)的化合物通过熟知的方法如碱性水解来制备,或可通过已知方法制备(Beilstein J.Org.Chem.2007,3,第23期)。
其中U1表示卤素的式(XXII)的化合物为市售可得的,或可由其中U1表示羟基的式(XXII)的化合物通过熟知方法来制备。
其中U1表示C1-C6-烷氧基的式(XXII)的化合物可由其中U1表示羟基的式(XXII)的化合物通过熟知方法来制备。
制备式(XXI)的化合物-方法PXXI(2)
式(XXI)的化合物(其中R4为氢原子或C1-C6-烷基)还可通过包括以下步骤的方法PXXI(2)来制备:将式(XXIV)的化合物进行重氮化,随后进行芳族取代,以提供式(XXI)的化合物,如以下反应方案所示:
方法PXXI(2)
其中R4为氢原子或C1-C6-烷基,U19为氨基、氯原子或溴原子且U20为氨基、氯原子或溴原子,条件是U19或U20中的至少一个为氨基。
方法PXXI(2)可根据已知方法进行(The Chemistry of diazonium and diazogroups;Saul Patai;Wiley-Interscience;1978;288-280和645-657;Account ofChemical Research(2018),51,496,以及其中所引用的参考文献)。
本文所定义的式(XXIV)的化合物可通过包括以下步骤的方法来制备:通过去保护反应使式(XXV)的化合物去保护,如以下反应方案所示:
其中R4为氢原子或C1-C6-烷基,U21为被保护的氨基、氯原子或溴原子且U22为被保护的氨基、氯原子或溴原子,条件是U21或U22中的至少一个为被保护的氨基,U19为氨基、氯原子或溴原子且U20为氨基、氯原子或溴原子,条件是U19或U20中的至少一个为氨基。
氨基的保护基团的实例包括:苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷基磺酰基、三氟甲基磺酰基、未取代或取代的苯基磺酰基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基。
去保护方法可根据除去保护基团的已知方法来进行(Greene's ProtectiveGroups in Organic Synthesis;Peter G.M.Wuts;Wiley;第五版;2014;895至1194)。例如,叔丁氧基羰基和苄氧基羰基保护基团可在酸性介质中(例如,用氢氯酸或三氟乙酸)除去。苄基型保护基团可在催化剂(例如负载于活性炭上的钯)的存在下以氢解方式用氢除去。三氟乙酰基可在碱性介质中(例如,用碳酸钾或氢氧化锂)除去。
式(XXIV)的化合物还可由式(XXVI)的化合物制备,而式(XXV)的化合物可通过使式(XXVII)的化合物与式(XXIII)的化合物在方法PXXI(1)中所述的条件下进行反应来制备:
其中U19、U20、U21和U22如本文所定义,U1为卤素原子、羟基或C1-C6-烷氧基。
式(XXVI)的化合物和式(XXVII)的化合物为市售可得的或可通过熟知方法用与制备式(XXII)的化合物所公开的反应条件类似的反应条件来制备。
制备式(XXI)的化合物-方法PXXI(3)
式(XXI)的化合物还可通过方法PXXI(3)由式(XXVIII)的化合物来制备,如以下反应方案所示:
方法PXXI(3)
其中R4为氢原子或C1-C6-烷基,R3与R1和R2不同且为氟原子或氯原子。
方法PXXI(3)可根据已知方法来进行(The Chemistry of diazonium and diazogroups;Saul Patai;Wiley-Interscience;1978;288-280和645-657;Account ofChemical Research(2018),51,496,以及其中所引用的参考文献)。
本文所定义的式(XXVIII)的化合物可通过包括以下步骤的方法来制备:通过去保护反应使式(XXIX)的化合物去保护,如以下反应方案所示:
其中R4为氢原子或C1-C6-烷基,U23为被保护的氨基。
氨基的保护基团的实例包括:苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷基磺酰基、三氟甲基磺酰基、未取代或取代的苯基磺酰基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基。
去保护方法可根据除去保护基团的已知方法来进行(Greene's ProtectiveGroups in Organic Synthesis;Peter G.M.Wuts;Wiley;第五版;2014;895至1194)。例如,叔丁氧基羰基和苄氧基羰基保护基团可在酸性介质中(例如,用氢氯酸或三氟乙酸)除去。苄基型保护基团可在催化剂(例如负载于活性碳上的钯)的存在下以氢解方式用氢除去。三氟乙酰基可在碱性介质中(例如,用碳酸钾或氢氧化锂)除去。
式(XXVIII)的化合物还可由式(XXX)的化合物制备,而式(XXIX)的化合物可由式(XXXI)的化合物通过与式(XXIII)的化合物在方法PXXI(1)中所述的条件下进行反应来制备:
其中U23如本文所定义且U1为卤素原子、羟基或C1-C6-烷氧基。
式(XXX)的化合物和式(XXXI)的化合物为市售可得的或可通过熟知方法用与制备式(XXII)的化合物所公开的反应条件类似的反应条件来制备。
制备式(XXI)的化合物-方法PXXI(4)
式(XXI)的化合物(其中R4为氢原子或C1-C6-烷基)可通过包括以下步骤的方法PXXI(4)来制备:使式(XXXII)的化合物与式(XXXIII)的化合物或其一种盐反应,如以下反应方案所示:
方法PXXI(4)
其中R4为氢原子或C1-C6-烷基,U2为溴原子、碘原子、甲磺酸根基团、甲苯磺酸根基团或三氟甲磺酸根基团,且U3为硼衍生物如硼酸、硼酸酯衍生物、三氟硼酸钾衍生物或可通过1至2个配体进行络合的卤化金属,如卤化镁或卤化锌。
方法PXXI(4)可根据已知方法在过渡金属催化剂(如钯)的存在下,且如果合适,在膦配体或N-杂环卡宾配体的存在下,如果合适,在碱的存在下且如果合适,在溶剂的存在下进行(WO2012054721、Angewandte Chemie International Edition(2017),56,1581、Angewandte Chemie International Edition(2017),56,7078及其中所引用的参考文献)。
方法PXXI(4)可在催化剂(如金属盐或络合物)的存在下进行。用于此目的的合适金属衍生物为过渡金属催化剂,如钯。用于此目的的合适金属盐或络合物为例如氯化钯、乙酸钯、四(三苯基膦)钯(0)、双(二亚苄基丙酮)钯(0)、三(二亚苄基丙酮)二钯(0)、双(三苯基膦)二氯化钯(II)、[1,1'-双(二苯基膦)二茂铁]二氯化钯(II)、双(肉桂基)二氯化二钯(II)、双(烯丙基)二氯化二钯(II)、[1,1'-双(二叔丁基膦)二茂铁]二氯化钯(II)、二-μ-碘双(三叔丁基膦)二钯(I)或二-μ-溴双(三叔丁基膦)二钯(I)。
还可以通过向反应中单独添加钯盐和配体或盐而在反应混合物中产生钯络合物,所述配体或盐为例如三乙基膦、三叔丁基膦、三叔丁基鏻四氟硼酸盐、三环己基膦、2-(二环己基膦)联苯、2-(二叔丁基膦)联苯、2-(二环己基膦)-2'-(N,N-二甲基氨基)联苯、2-(叔丁基膦)-2'-(N,N-二甲基氨基)联苯、2-二叔丁基膦-2',4',6'-三异丙基联苯、2-二环己基膦-2',4',6'-三异丙基联苯、2-二环己基膦-2,6'-二甲氧基联苯、2-二环己基膦-2',6'-二异丙氧基联苯、三苯基膦、三-(邻甲苯基)膦、3-(二苯基膦)苯磺酸钠、三-2-(甲氧基苯基)膦、2,2'-双(二苯基膦)-1,1'-联萘、1,4-双(二苯基膦)丁烷、1,2-双(二苯基膦)乙烷、1,4-双(二环己基膦)丁烷、1,2-双(二环己基膦)乙烷、2-(二环己基膦)-2'-(N,N-二甲基氨基)-联苯、1,1'-双(二苯基膦)-二茂铁、(R)-(-)-1-[(S)-2-二苯基膦)二茂铁基]乙基二环己基膦、三-(2,4-叔丁基苯基)亚磷酸酯、二(1-金刚烷基)-2-吗啉基苯基膦或1,3-双(2,4,6-三甲基苯基)咪唑鎓氯化物。
还有利的是选择来自商业目录的合适的催化剂和/或配体,所述商业目录为例如Strem Chemicals的《有机合成的金属催化剂(Metal Catalysts for OrganicSynthesis)》”或Strem Chemicals的《磷配体及化合物(Phosphorous Ligands andCompounds)》。
用于进行方法PXXI(4)的合适碱可为常用于这些反应的无机碱和有机碱。优选使用碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾或其他氢氧化铵衍生物;碱土金属、碱金属或铵氟化物,如氟化钾、氟化铯或四丁基氟化铵;碱土金属或碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铯;碱金属或碱土金属乙酸盐,如乙酸钠、乙酸锂、乙酸钾或乙酸钙;碱金属或碱土金属磷酸盐,如磷酸三钾;碱金属醇盐,如叔丁醇钾或叔丁醇钠;叔胺,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二环己基甲胺、N,N-二异丙基乙胺、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU);以及芳族碱,如吡啶、甲基吡啶、二甲基吡啶或三甲基吡啶。
用于进行方法PXXI(4)的合适溶剂可为常用的惰性有机溶剂。优选使用任选卤代的脂族、脂环族或芳族烃,如石油醚、戊烷、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、2-甲基四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正丁腈或异丁腈或苯甲腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;脲,如1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮;酯,如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜;或砜,如环丁砜;及其混合物。
还可有利的使用共溶剂如水或醇进行方法PXXI(4),所述醇为例如甲醇、乙醇、丙醇、异丙醇或叔丁醇。
方法PXXI(4)可在惰性气氛如氩气或氮气气氛中进行。当进行方法PXXI(4)时,每摩尔式(XXXII)的化合物可使用1摩尔或过量的式(XXXIII)的化合物和1至5摩尔的碱以及0.01至20摩尔%的钯络合物。还可使用以其他比例的反应组分。后处理通过已知方法进行。
式(XXXIII)的化合物为市售可得的或可通过熟知的方法制备。
式(XXXII)的化合物可通过使式(XXXIV)的化合物与式(XXIII)的化合物在方法PXXI(1)中所描述的条件下进行反应来制备:
其中U2和U1如本文中所定义。
式(XXXIV)的化合物(其中U2为氯原子、溴原子或碘原子)为市售可得的或可通过熟知的方法采用与制备式(XXII)的化合物所公开的反应条件类似的反应条件来制备。
式(XXXIV)的化合物(其中U2为甲磺酸根基团、甲苯磺酸根基团或三氟甲磺酸根基团)可通过熟知的方法由在U2位带有羟基的相应化合物来制备。
制备式(XXI)的化合物-方法PXXI(5)
式(XXI)的化合物(其中R4为氢原子或C1-C6-烷基)可通过方法PXXI(5)进行氟化反应来制备,如以下方案所示:
方法PXXI(5)
其中R4为氢原子或C1-C6-烷基。
方法PXXI(5)可根据已知方法来进行(Journal of the American ChemicalSociety 2011,133,11482和Organic Process Research&Development 2014,18,1041)。
可根据上述方法来制备本发明的化合物。然而,应理解,本领域技术人员基于其常识和可获得的出版物,将能够根据想要合成的本发明的每种化合物的具体情况来调节这些方法。
本文所公开的中间体可有效地防治细菌和/或真菌。
用于制备式(III)的化合物的中间体
本发明涉及用于制备式(III)的化合物的中间体。
除非另有说明,在下文中,R1、R2和R3具有如上文针对式(III)的化合物所给出的相同含义。
提供式(XXI)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;并且R4为氢原子或C1-C6-烷基。
提供式(XXIIa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;并且
条件是当R1和R2为氯原子时,R3不为氯原子;
U1a为羟基或C1-C6-烷氧基;
条件是式(XXIIa)的化合物不表示:
-4,5-二氯-3-氟噻吩-2-甲酸甲酯[2166596-88-7],
-4,5-二氯-3-氟噻吩-2-甲酸[2166596-87-6],
-4,5-二溴-3-氟噻吩-2-甲酸乙酯[2260624-98-2],
-4,5-二溴-3-氟噻吩-2-甲酸[1628447-64-2],
-4,5-二溴-3-氯噻吩-2-甲酸甲酯[1501789-47-4],
-4,5-二溴-3-碘噻吩-2-甲酸[854626-46-3],
-4,5-二溴-3-氯噻吩-2-甲酸[503308-99-4],
-4,5-二溴-3-氯噻吩-2-甲酸乙酯[503308-98-3],
-4,5-二溴-3-氟噻吩-2-甲酸甲酯[395664-58-1],
-3,4,5-三溴噻吩-2-甲酸叔丁酯[62224-27-5],
-3,4,5-三溴噻吩-2-甲酸乙酯[54113-44-9],
-3,4,5-三溴噻吩-2-甲酸[53317-05-8],
-3,4,5-三溴噻吩-2-甲酸甲酯[24647-80-1],
-4,5-二溴-3-甲基噻吩-2-甲酸乙酯[2088257-63-8],
-4,5-二氯-3-甲基噻吩-2-甲酸[854626-34-9],
-4,5-二溴-3-甲基噻吩-2-甲酸[854626-32-7],
-4,5-二氯-3-甲基噻吩-2-甲酸甲酯[854626-27-0],和
-4,5-二溴-3-甲基噻吩-2-甲酸甲酯[648412-53-7]。
式(XXIVa)和(XXIVb)的化合物:
其中
R1或R2为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;并且
R4为氢原子或C1-C6-烷基。
提供式(XXVa)和(XXVb)的化合物:
其中
R1或R2为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;
R4为氢原子或C1-C6-烷基;
V为苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基。
提供式(XXVIa)和(XXVIb)的化合物:
其中
R1或R2为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;
U1a为羟基或C1-C6-烷氧基,
条件是式(XXVIa)的化合物不表示:
-5-氨基-4-溴-3-甲基噻吩-2-甲酸乙酯[851443-15-7];
且条件是式(XXVIb)的化合物不表示:
4-氨基-3,5-二溴噻吩-2-甲酸乙酯[1394375-09-7]。
提供式(XXVIIa)和(XXVIIb)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;
V为苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基;并且
U1a为羟基或C1-C6-烷氧基,
条件是式(XXVIIa)的化合物不表示:
-5-乙酰氨基-4-溴-3-甲基噻吩-2-甲酸乙酯[851444-63-8]。
提供式(XXVIII)和(XXIXa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R4为氢原子或C1-C6-烷基;
V为苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基。
提供式(XXXa)和(XXXIa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
V为苄基、4-甲氧基苄基、烯丙基、未取代或取代的C1-C6-烷氧基羰基、未取代或取代的苄氧基羰基、烯丙氧基羰基、乙酰基或三氟乙酰基;并且
U1a为羟基或C1-C6-烷氧基,
条件是式(XXXa)的化合物不表示:
-3-氨基-4,5-二氯噻吩-2-甲酸甲酯[1621488-35-4],
且条件是式(XXXIa)的化合物不表示:
-3-乙酰氨基-4,5-二氯噻吩-2-甲酸[2090448-72-7],
-3-乙酰氨基-4,5-二氯噻吩-2-甲酸甲酯[632356-39-9],和
-4,5-二氯-3-[(甲氧基羰基)氨基]噻吩-2-甲酸甲酯[35707-28-9]。
提供式(XXXIIa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R4为氢原子或C1-C6-烷基;并且
U2a为溴原子、碘原子、甲磺酸根基团、甲苯磺酸根基团或三氟甲磺酸根基团,条件是当R1和R2为溴原子时,U2a不为溴原子。
提供式(XXXIVa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
U2b为甲磺酸根基团、甲苯磺酸根基团或三氟甲磺酸根基团;并且
U1a为羟基或C1-C6-烷氧基。
提供式(XXXV)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;并且
R4为氢原子或C1-C6-烷基。
所公开的中间体可有效地防治细菌和/或真菌。
组合物和制剂
本发明还涉及一种组合物,特别是用于防治由黄单胞菌属的细菌所引起的植物病害的组合物,其包含一或多种上文所公开的式(III)的化合物及其任意混合物。
组合物通常包含至少一种式(III)的化合物和至少一种农业上合适的助剂,例如一种或多种载体和/或一种或多种表面活性剂。
载体为通常是惰性的天然或合成的固体或液体有机或无机物质。载体通常改善化合物在例如植物、植物部位或种子上的施用。合适的固体载体的实例包括但不限于:铵盐、天然石粉(如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石和硅藻土),以及合成石粉(如细分散的二氧化硅、氧化铝和硅酸盐)。通常用于制备颗粒剂的固体载体的实例包括但不限于:粉碎并分级的天然岩石(如方解石、大理石、浮石、海泡石和白云石)、无机和有机粉的合成颗粒,以及有机材料(如纸、锯屑、椰壳、玉米穗轴和烟草秸秆)的颗粒。合适的液体载体的实例包括但不限于水、有机溶剂及其组合。合适的溶剂的实例包括极性和非极性有机化学液体,例如来自以下类别:芳族和非芳族烃类(如环己烷、石蜡、烷基苯、二甲苯、甲苯烷基萘、氯化芳族烃或氯化脂族烃如氯苯、氯乙烯或二氯甲烷)、醇和多元醇(其还可以任选地被取代、醚化和/或酯化,如丁醇或乙二醇)、酮(如丙酮、甲基乙基酮、甲基异丁基酮或环己酮)、酯(包括脂肪与油类)和(聚)醚、未取代和取代的胺、酰胺(如二甲基甲酰胺)、内酰胺(如N-烷基吡咯烷酮)和内酯、砜和亚砜(如二甲基亚砜)。载体还可以是液化气态增量剂,即在标准温度和标准压力下呈气态的液体,例如气溶胶推进剂,如卤代烃、丁烷、丙烷、氮气和二氧化碳。载体的量通常为组合物重量的1至99.99%,优选5至99.9%,更优选10至99.5%,最优选20至99%。
表面活性剂可以是离子型(阳离子型或阴离子型)或非离子型表面活性剂,如离子型或非离子型乳化剂、泡沫形成剂、分散剂、润湿剂及其任意混合物。合适的表面活性剂的实例包括但不限于,聚丙烯酸的盐;木素磺酸的盐;苯酚磺酸或萘磺酸的盐;环氧乙烷和/或环氧丙烷与脂肪醇、脂肪酸或脂肪胺的缩聚物(聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚);取代的酚(优选烷基酚或芳基酚);磺基琥珀酸酯的盐;牛磺酸衍生物(优选烷基牛磺酸酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯和含有硫酸根、磺酸根、磷酸根的化合物的衍生物(例如,烷基磺酸酯、烷基硫酸酯、芳基磺酸酯);以及蛋白质水解物;木质素亚硫酸盐废液和甲基纤维素。当本发明的化合物和/或载体不溶于水并且用水施用时,通常使用表面活性剂。然后,表面活性剂的量通常为组合物重量的5%至40%。
合适的助剂的其他实例包括防水剂、干燥剂、粘合剂(binder)(胶粘剂(adhesive)、增粘剂、固定剂,如羧甲基纤维素,粉末、颗粒或胶乳形式的天然和合成聚合物(如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯)、天然磷脂(如脑磷脂和卵磷脂)和合成磷脂、聚乙烯吡咯烷酮和甲基纤维素)、增稠剂、稳定剂(例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或其它改善化学和/或物理稳定性的试剂)、染料或颜料(如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;有机染料,例如茜素、偶氮和金属酞菁染料)、消泡剂(例如硅酮消泡剂和硬脂酸镁)、防腐剂(例如二氯苯和苄醇半缩甲醛)、二次增稠剂(纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细分散的二氧化硅)、粘着剂、赤霉素和加工助剂、矿物油和植物油、香料、蜡、营养物(包括微量营养物,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐)、保护胶体、触变物质、渗透剂、螯合剂和络合剂。
助剂的选择与本发明的化合物的预期施用方式和/或物理特性有关。此外,可以选择助剂以赋予组合物或由其制备的使用形式特定的特性(技术、物理和/或生物学特性)。助剂的选择可以使得针对具体需求来定制组合物。
本发明的组合物可以是任何常规形式,如溶液剂(例如水溶液)、乳剂、可湿性粉剂、水基和油基悬浮剂、粉末剂、粉剂、膏剂、可溶性粉剂、可溶性颗粒剂、撒播用颗粒剂、悬乳浓缩剂、用本发明的一种或多种化合物浸渍的天然或合成产品、肥料以及聚合物中的微胶囊剂。本发明的化合物可以悬浮、乳化或溶解的形式存在。
本发明的组合物可以作为即用型制剂提供给最终使用者,即可以通过合适的装置如喷雾或撒粉装置将组合物直接施用于植物或种子。或者,组合物可以浓缩物的形式提供给最终使用者,在使用前必须将其稀释,优选用水稀释。
本发明的组合物可以常规方式制备,例如通过将本发明的一种或多种化合物与一种或多种合适的助剂(例如上文所公开的)进行混合来制备。
本发明的组合物通常含有0.01至99重量%,0.05至98重量%,优选0.1至95重量%,更优选0.5至90重量%,最优选1至80重量%的一种或多种本发明化合物。组合物可包含两种以上的本发明的化合物。在这种情况下,所述范围是指本发明化合物的总量。
混合物/结合物
本发明的一种或多种化合物和组合物可以与其他活性成分(如杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂、杀昆虫剂、除草剂、肥料、生长调节剂、安全剂和/或化学信息素)混合。这可以拓宽活性谱或防止抗性发展。已知的杀真菌剂、杀昆虫剂、杀螨剂、杀线虫剂和杀细菌剂的实例公开于《农药手册(Pesticide Manual)》,第17版。
可以与本发明的一种或多种化合物和组合物混合的尤其优选的杀真菌剂的实例为:
1)麦角甾醇生物合成抑制剂,例如(1.001)环丙唑醇(cyproconazole)、(1.002)苯醚甲环唑(difenoconazole)、(1.003)氟环唑(epoxiconazole)、(1.004)环酰菌胺(fenhexamid)、(1.005)苯锈啶(fenpropidin)、(1.006)丁苯吗啉(fenpropimorph)、(1.007)胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009)粉唑醇(flutriafol)、(1.010)烯菌灵(imazalil)、(1.011)烯菌灵硫酸盐(imazalil sulfate)、(1.012)种菌唑(ipconazole)、(1.013)叶菌唑(metconazole)、(1.014)腈菌唑(myclobutanil)、(1.015)多效唑(paclobutrazol)、(1.016)咪鲜胺(prochloraz)、(1.017)丙环唑(propiconazole)、(1.018)丙硫菌唑(prothioconazole)、(1.019)氯啶菌酯(pyrisoxazole)、(1.020)螺环菌胺(spiroxamine)、(1.021)戊唑醇(tebuconazole)、(1.022)氟醚唑(tetraconazole)、(1.023)三唑醇(triadimenol)、(1.024)克啉菌(tridemorph)、(1.025)灭菌唑(triticonazole)、(1.026)(1R,2S,5S)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.027)(1S,2R,5R)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.028)(2R)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.029)(2R)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031)(2S)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032)(2S)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.035)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.036)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.037)1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.038)1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.039)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.040)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.041)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.042)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.043)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.044)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.045)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.046)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.047)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.048)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.049)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.050)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.051)2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052)2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055)氯氟醚菌唑(Mefentrifluconazole)、(1.056)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.057)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.058)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.059)5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.060)5-(烯丙基硫基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.061)5-(烯丙基硫基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.063)N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基甲脒、(1.064)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基甲脒、(1.065)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫基}苯基)-N-乙基-N-甲基甲脒、(1.066)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基甲脒、(1.067)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基甲脒、(1.068)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基甲脒、(1.069)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫基]苯氧基}苯基)-N-乙基-N-甲基甲脒、(1.070)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基甲脒、(1.071)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基甲脒、(1.072)N'-(4-{[3-(二氟甲氧基)苯基]硫基}-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、(1.073)N'-(4-{3-[(二氟甲基)硫基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、(1.074)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基甲脒、(1.075)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基甲脒、(1.076)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基甲脒、(1.077)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基甲脒、(1.078)N'-{5-溴-6-[(顺式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基甲脒、(1.079)N'-{5-溴-6-[(反式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基甲脒、(1.080)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基甲脒、(1.081)Ipfentrifluconazole。
2)呼吸链复合物I或II的抑制剂,例如(2.001)苯并烯氟菌唑(benzovindiflupyr)、(2.002)联苯吡菌胺(bixafen)、(2.003)啶酰菌胺(boscalid)、(2.004)萎锈灵(carboxin)、(2.005)氟吡菌酰胺(fluopyram)、(2.006)氟酰胺(flutolanil)、(2.007)氟唑菌酰胺(fluxapyroxad)、(2.008)呋吡菌胺(furametpyr)、(2.009)噻吩酰菌酮(Isofetamid)、(2.010)吡唑萘菌胺(isopyrazam)(反式差向异构对映异构体1R,4S,9S)、(2.011)吡唑萘菌胺(反式差向异构对映异构体1S,4R,9R)、(2.012)吡唑萘菌胺(反式差向异构外消旋体1RS,4SR,9SR)、(2.013)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS和反式差向异构外消旋体1RS,4SR,9SR的混合物)、(2.014)吡唑萘菌胺(顺式差向异构对映异构体1R,4S,9R)、(2.015)吡唑萘菌胺(顺式差向异构对映异构体1S,4R,9S)、(2.016)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.017)氟唑菌苯胺(penflufen)、(2.018)吡噻菌胺(penthiopyrad)、(2.019)氟唑菌酰羟胺(pydiflumetofen)、(2.020)pyraziflumid、(2.021)氟唑环菌胺(sedaxane)、(2.022)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.023)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.024)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.026)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(2.027)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.028)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.029)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.030)fluindapyr、(2.031)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.032)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.033)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034)N-(2-环戊基-5-氟苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.035)N-(2-叔丁基-5-甲基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.036)N-(2-叔丁基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.037)N-(5-氯-2-乙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.038)isoflucypram、(2.039)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.040)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.041)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.042)N-[2-氯-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.043)N-[3-氯-2-氟-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.044)N-[5-氯-2-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.045)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基]-1H-吡唑-4-甲酰胺、(2.046)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.047)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.048)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-硫代甲酰胺、(2.049)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.050)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.051)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.052)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.053)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.054)N-环丙基-N-(2-环丙基-5-氟苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.055)N-环丙基-N-(2-环丙基-5-甲基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.056)N-环丙基-N-(2-环丙基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.057)pyrapropoyne。
3)呼吸链复合物III的抑制剂,例如(3.001)唑嘧菌胺(ametoctradin)、(3.002)安美速(amisulbrom)、(3.003)腈嘧菌酯(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)氰霜唑(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastrobin)、(3.009)唑菌酮(famoxadone)、(3.010)咪唑菌酮(fenamidone)、(3.011)氟菌螨酯(flufenoxystrobin)、(3.012)氟嘧菌酯(fluoxastrobin)、(3.013)醚菌酯(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015)肟醚菌胺(orysastrobin)、(3.016)啶氧菌酯(picoxystrobin)、(3.017)唑菌胺酯(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.019)唑胺菌酯(pyraoxystrobin)、(3.020)肟菌酯(trifloxystrobin)、(3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.022)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.023)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.024)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.025)(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基2-甲基丙酸酯、(3.026)mandestrobin、(3.027)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰胺基-2-羟基苯甲酰胺、(3.028)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.029){5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苄基}氨基甲酸甲酯、(3.030)metyltetraprole、(3.031)florylpicoxamid。
4)有丝分裂和细胞分裂抑制剂,例如(4.001)多菌灵(carbendazim)、(4.002)乙霉威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolide)、(4.005)戊菌隆(pencycuron)、(4.006)噻苯咪唑(thiabendazole)、(4.007)甲基硫菌灵(thiophanate-methyl)、(4.008)苯酰菌胺(zoxamide)、(4.009)3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基哒嗪、(4.010)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(4.011)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪、(4.012)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(4.023)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5)具有多位点活性的化合物,例如(5.001)波尔多液(bordeaux mixture)、(5.002)敌菌丹(captafol)、(5.003)克菌丹(captan)、(5.004)百菌清(chlorothalonil)、(5.005)氢氧化铜、(5.006)环烷酸铜(copper naphthenate)、(5.007)氧化铜、(5.008)氧氯化铜(copper oxychloride)、(5.009)硫酸铜(2+)(copper(2+)sulfate)、(5.010)二噻农(dithianon)、(5.011)多果定(dodine)、(5.012)灭菌丹(folpet)、(5.013)代森锰锌(mancozeb)、(5.014)代森锰(maneb)、(5.015)代森联(metiram)、(5.016)代森联锌(metiram zinc)、(5.017)喹啉铜(oxine-copper)、(5.018)丙森锌(propineb)、(5.019)硫和硫制剂(包括多硫化钙)、(5.020)福美双(thiram)、(5.021)代森锌(zineb)、(5.022)福美锌(ziram)、(5.023)6-乙基-5,7-二氧代-6,7-二氢-5H-吡咯并[3',4':5,6][1,4]二噻英并[2,3-c][1,2]噻唑-3-甲腈。
6)诱导宿主防御的化合物,例如(6.001)阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、(6.002)异噻菌胺(isotianil)、(6.003)烯丙苯噻唑(probenazole)、(6.004)噻酰菌胺(tiadinil)。
7)氨基酸和/或蛋白质生物合成抑制剂,例如(7.001)嘧菌环胺(cyprodinil)、(7.002)春雷霉素(kasugamycin)、(7.003)春雷霉素盐酸盐水合物(kasugamycinhydrochloride hydrate)、(7.004)土霉素(oxytetracycline)、(7.005)嘧霉胺(pyrimethanil)、(7.006)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉。
8)ATP生成抑制剂,例如(8.001)硅噻菌胺(silthiofam)。
9)细胞壁合成抑制剂,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002)烯酰吗啉(dimethomorph)、(9.003)氟吗啉(flumorph)、(9.004)缬霉威(iprovalicarb)、(9.005)双炔酰菌胺(mandipropamid)、(9.006)丁吡吗啉(pyrimorph)、(9.007)缬菌胺(valifenalate)、(9.008)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮。
10)脂和膜合成抑制剂,例如(10.001)霜霉威(propamocarb)、(10.002)霜霉威盐酸盐(propamocarb hydrochloride)、(10.003)甲基立枯磷(tolclofos-methyl)。
11)黑色素生物合成抑制剂,例如(11.001)三环唑(tricyclazole)、(11.002){3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸2,2,2-三氟乙酯。
12)核酸合成抑制剂,例如(12.001)苯霜灵(benalaxyl)、(12.002)高效苯霜灵(benalaxyl-M)(kiralaxyl)、(12.003)甲霜灵(metalaxyl)、(12.004)高效甲霜灵(metalaxyl-M)(mefenoxam)。
13)信号转导抑制剂,例如(13.001)咯菌腈(fludioxonil)、(13.002)异菌脲(iprodione)、(13.003)腐霉利(procymidone)、(13.004)丙氧喹啉(proquinazid)、(13.005)喹氧灵(quinoxyfen)、(13.006)乙烯菌核利(vinclozolin)。
14)用作解偶联剂的化合物,例如(14.001)氟啶胺(fluazinam)、(14.002)消螨多(meptyldinocap)。
15)其他化合物,例如(15.001)脱落酸(abscisic acid)、(15.002)苯噻硫氰(benthiazole)、(15.003)bethoxazin、(15.004)卡巴西霉素(capsimycin)、(15.005)香芹酮(carvone)、(15.006)灭螨锰(chinomethionat)、(15.007)硫杂灵(cufraneb)、(15.008)环氟菌胺(cyflufenamid)、(15.009)霜脲氰(cymoxanil)、(15.010)环丙磺酰胺(cyprosulfamide)、(15.011)flutianil、(15.012)三乙膦酸铝(fosetyl-aluminium)、(15.013)乙膦酸钙(fosetyl-calcium)、(15.014)乙膦酸钠(fosetyl-sodium)、(15.015)异硫氰酸甲酯(methyl isothiocyanate)、(15.016)苯菌酮(metrafenone)、(15.017)灭粉霉素(mildiomycin)、(15.018)游霉素(natamycin)、(15.019)二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、(15.020)酞菌酯(nitrothal-isopropyl)、(15.021)oxamocarb、(15.022)Oxathiapiprolin、(15.023)oxyfenthiin、(15.024)五氯苯酚(pentachlorophenol)及盐、(15.025)亚磷酸及其盐、(15.026)霜霉威-乙膦酸盐(propamocarb-fosetylate)、(15.027)pyriofenone(chlazafenone)、(15.028)tebufloquin、(15.029)叶枯酞(tecloftalam)、(15.030)甲磺菌胺(tolnifanide)、(15.031)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.032)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.033)2-(6-苄基吡啶-2-基)喹唑啉、(15.034)dipymetitrone、(15.035)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.036)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.037)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.038)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.039)2-{(5R)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-唑-5-基}-3-氯苯基甲磺酸酯、(15.040)2-{(5S)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-唑-5-基}-3-氯苯基甲磺酸酯、(15.041)Ipflufenoquin、(15.042)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-唑-5-基}-3-氯苯基甲磺酸酯、(15.044)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-唑-5-基}苯基甲磺酸酯、(15.045)2-苯基苯酚及盐、(15.046)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.047)quinofumelin、(15.048)4-氨基-5-氟嘧啶-2-醇(互变异构形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.049)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.050)5-氨基-1,3,4-噻二唑-2-硫醇、(15.051)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、(15.052)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.053)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.054)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氢-1,4-苯并氧杂吖庚因、(15.055){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁-3-炔-1-基酯、(15.056)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.057)吩嗪-1-甲酸、(15.058)3,4,5-三羟基苯甲酸丙酯、(15.059)喹啉-8-醇、(15.060)喹啉-8-醇硫酸酯(2:1)、(15.061){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯、(15.062)5-氟-4-亚氨基-3-甲基-1-[(4-甲基苯基)磺酰基]-3,4-二氢嘧啶-2(1H)-酮、(15.063)aminopyrifen。
如上文所述的(1)至(15)类的所有命名的混合配伍剂可以游离化合物的形式,和/或如果其官能团允许,以其农业上可接受的盐的形式存在。
在一些实施方案中,化合物结合物包含以下组分:
(III.01)+(1.001)、(III.01)+(1.002)、(III.01)+(1.003)、(III.01)+(1.004)、(III.01)+(1.005)、(III.01)+(1.006)、(III.01)+(1.007)、(III.01)+(1.008)、(III.01)+(1.009)、(III.01)+(1.010)、(III.01)+(1.011)、(III.01)+(1.012)、(III.01)+(1.013)、(III.01)+(1.014)、(III.01)+(1.015)、(III.01)+(1.016)、(III.01)+(1.017)、(III.01)+(1.018)、(III.01)+(1.019)、(III.01)+(1.020)、(III.01)+(1.021)、(III.01)+(1.022)、(III.01)+(1.023)、(III.01)+(1.024)、(III.01)+(1.025)、(III.01)+(1.026)、(III.01)+(1.027)、(III.01)+(1.028)、(III.01)+(1.029)、(III.01)+(1.030)、(III.01)+(1.031)、(III.01)+(1.032)、(III.01)+(1.033)、(III.01)+(1.034)、(III.01)+(1.035)、(III.01)+(1.036)、(III.01)+(1.037)、(III.01)+(1.038)、(III.01)+(1.039)、(III.01)+(1.040)、(III.01)+(1.041)、(III.01)+(1.042)、(III.01)+(1.043)、(III.01)+(1.044)、(III.01)+(1.045)、(III.01)+(1.046)、(III.01)+(1.047)、(III.01)+(1.048)、(III.01)+(1.049)、(III.01)+(1.050)、(III.01)+(1.051)、(III.01)+(1.052)、(III.01)+(1.053)、(III.01)+(1.054)、(III.01)+(1.055)、(III.01)+(1.056)、(III.01)+(1.057)、(III.01)+(1.058)、(III.01)+(1.059)、(III.01)+(1.060)、(III.01)+(1.061)、(III.01)+(1.062)、(III.01)+(1.063)、(III.01)+(1.064)、(III.01)+(1.065)、(III.01)+(1.066)、(III.01)+(1.067)、(III.01)+(1.068)、(III.01)+(1.069)、(III.01)+(1.070)、(III.01)+(1.071)、(III.01)+(1.072)、(III.01)+(1.073)、(III.01)+(1.074)、(III.01)+(1.075)、(III.01)+(1.076)、(III.01)+(1.077)、(III.01)+(1.078)、(III.01)+(1.079)、(III.01)+(1.080)、(III.01)+(1.081)、(III.01)+(1.082)、(III.01)+(1.083)、(III.01)+(1.084)、(III.01)+(1.085)、(III.01)+(1.086)、(III.01)+(2.001)、(III.01)+(2.002)、(III.01)+(2.003)、(III.01)+(2.004)、(III.01)+(2.005)、(III.01)+(2.006)、(III.01)+(2.007)、(III.01)+(2.008)、(III.01)+(2.009)、(III.01)+(2.010)、(III.01)+(2.011)、(III.01)+(2.012)、(III.01)+(2.013)、(III.01)+(2.014)、(III.01)+(2.015)、(III.01)+(2.016)、(III.01)+(2.017)、(III.01)+(2.018)、(III.01)+(2.019)、(III.01)+(2.020)、(III.01)+(2.021)、(III.01)+(2.022)、(III.01)+(2.023)、(III.01)+(2.024)、(III.01)+(2.025)、(III.01)+(2.026)、(III.01)+(2.027)、(III.01)+(2.028)、(III.01)+(2.029)、(III.01)+(2.030)、(III.01)+(2.031)、(III.01)+(2.032)、(III.01)+(2.033)、(III.01)+(2.034)、(III.01)+(2.035)、(III.01)+(2.036)、(III.01)+(2.037)、(III.01)+(2.038)、(III.01)+(2.039)、(III.01)+(2.040)、(III.01)+(2.041)、(III.01)+(2.042)、(III.01)+(2.043)、(III.01)+(2.044)、(III.01)+(2.045)、(III.01)+(2.046)、(III.01)+(2.047)、(III.01)+(2.048)、(III.01)+(2.049)、(III.01)+(2.050)、(III.01)+(2.051)、(III.01)+(2.052)、(III.01)+(2.053)、(III.01)+(2.054)、(III.01)+(2.055)、(III.01)+(2.056)、(III.01)+(3.001)、(III.01)+(3.002)、(III.01)+(3.003)、(III.01)+(3.004)、(III.01)+(3.005)、(III.01)+(3.006)、(III.01)+(3.007)、(III.01)+(3.008)、(III.01)+(3.009)、(III.01)+(3.010)、(III.01)+(3.011)、(III.01)+(3.012)、(III.01)+(3.013)、(III.01)+(3.014)、(III.01)+(3.015)、(III.01)+(3.016)、(III.01)+(3.017)、(III.01)+(3.018)、(III.01)+(3.019)、(III.01)+(3.020)、(III.01)+(3.021)、(III.01)+(3.022)、(III.01)+(3.023)、(III.01)+(3.024)、(III.01)+(3.025)、(III.01)+(3.026)、(III.01)+(3.027)、(III.01)+(3.028)、(III.01)+(3.029)、(III.01)+(3.030)、(III.01)+(4.001)、(III.01)+(4.002)、(III.01)+(4.003)、(III.01)+(4.004)、(III.01)+(4.005)、(III.01)+(4.006)、(III.01)+(4.007)、(III.01)+(4.008)、(III.01)+(4.009)、(III.01)+(4.010)、(III.01)+(4.011)、(III.01)+(4.012)、(III.01)+(4.013)、(III.01)+(4.014)、(III.01)+(4.015)、(III.01)+(4.016)、(III.01)+(4.017)、(III.01)+(4.018)、(III.01)+(4.019)、(III.01)+(4.020)、(III.01)+(4.021)、(III.01)+(4.022)、(III.01)+(4.023)、(III.01)+(4.024)、(III.01)+(4.025)、(III.01)+(5.001)、(III.01)+(5.002)、(III.01)+(5.003)、(III.01)+(5.004)、(III.01)+(5.005)、(III.01)+(5.006)、(III.01)+(5.007)、(III.01)+(5.008)、(III.01)+(5.009)、(III.01)+(5.010)、(III.01)+(5.011)、(III.01)+(5.012)、(III.01)+(5.013)、(III.01)+(5.014)、(III.01)+(5.015)、(III.01)+(5.016)、(III.01)+(5.017)、(III.01)+(5.018)、(III.01)+(5.019)、(III.01)+(5.020)、(III.01)+(5.021)、(III.01)+(5.022)、(III.01)+(5.023)、(III.01)+(6.001)、(III.01)+(6.002)、(III.01)+(6.003)、(III.01)+(6.004)、(III.01)+(7.001)、(III.01)+(7.002)、(III.01)+(7.003)、(III.01)+(7.004)、(III.01)+(7.005)、(III.01)+(7.006)、(III.01)+(8.001)、(III.01)+(9.001)、(III.01)+(9.002)、(III.01)+(9.003)、(III.01)+(9.004)、(III.01)+(9.005)、(III.01)+(9.006)、(III.01)+(9.007)、(III.01)+(9.008)、(III.01)+(9.009)、(III.01)+(10.001)、(III.01)+(10.002)、(III.01)+(10.003)、(III.01)+(11.001)、(III.01)+(11.002)、(III.01)+(12.001)、(III.01)+(12.002)、(III.01)+(12.003)、(III.01)+(12.004)、(III.01)+(13.001)、(III.01)+(13.002)、(III.01)+(13.003)、(III.01)+(13.004)、(III.01)+(13.005)、(III.01)+(13.006)、(III.01)+(14.001)、(III.01)+(14.002)、(III.01)+(15.001)、(III.01)+(15.002)、(III.01)+(15.003)、(III.01)+(15.004)、(III.01)+(15.005)、(III.01)+(15.006)、(III.01)+(15.007)、(III.01)+(15.008)、(III.01)+(15.009)、(III.01)+(15.010)、(III.01)+(15.011)、(III.01)+(15.012)、(III.01)+(15.013)、(III.01)+(15.014)、(III.01)+(15.015)、(III.01)+(15.016)、(III.01)+(15.017)、(III.01)+(15.018)、(III.01)+(15.019)、(III.01)+(15.020)、(III.01)+(15.021)、(III.01)+(15.022)、(III.01)+(15.023)、(III.01)+(15.024)、(III.01)+(15.025)、(III.01)+(15.026)、(III.01)+(15.027)、(III.01)+(15.028)、(III.01)+(15.029)、(III.01)+(15.030)、(III.01)+(15.031)、(III.01)+(15.032)、(III.01)+(15.033)、(III.01)+(15.034)、(III.01)+(15.035)、(III.01)+(15.036)、(III.01)+(15.037)、(III.01)+(15.038)、(III.01)+(15.039)、(III.01)+(15.040)、(III.01)+(15.041)、(III.01)+(15.042)、(III.01)+(15.043)、(III.01)+(15.044)、(III.01)+(15.045)、(III.01)+(15.046)、(III.01)+(15.047)、(III.01)+(15.048)、(III.01)+(15.049)、(III.01)+(15.050)、(III.01)+(15.051)、(III.01)+(15.052)、(III.01)+(15.053)、(III.01)+(15.054)、(III.01)+(15.055)、(III.01)+(15.056)、(III.01)+(15.057)、(III.01)+(15.058)、(III.01)+(15.059)、(III.01)+(15.060)、(III.01)+(15.061)、(III.01)+(15.062)、(III.01)+(15.063)、(III.01)+(15.064)、(III.01)+(15.065)、(III.01)+15.066)、(III.01)+(15.067)、(III.01)+(15.068)、(III.01)+(15.069)、(III.01)+(15.070)、(III.01)+(15.071)、(III.01)+(15.072)、(III.01)+(15.073)、(III.01)+(15.074)、(III.01)+(15.075)、(III.01)+(15.076)、(III.01)、(III.01)+(15.077)、(III.01)+(15.078)、(III.01)+(15.079)、(III.01)+(15.080)、(III.01)+(15.081)、(III.01)+(15.082)、(III.01)+(15.083)、(III.01)+(15.084)、(III.01)+(15.085)、(III.01)+(15.086)、(III.01)+(15.087)、(III.01)+(15.088)、(III.01)+(15.089)、(III.01)+(15.090)、(III.01)+(15.091)、(III.01)+(15.092)、(III.01)+(15.093)、(III.01)+(15.094)、(III.01)+(15.095)、(III.01)+(15.096)、(III.01)+(15.097)、(III.01)+(15.098)、(III.01)+(15.099)、(III.01)+(15.100)、(III.01)+(15.101)、(III.01)+(15.102)、(III.01)+(15.103)、(III.01)+(15.104)、(III.01)+(15.105)、(III.01)+(15.106)、(III.01)+(15.107)、(III.01)+(15.108)、(III.01)+(15.109)、(III.01)+(15.110)、(III.01)+(15.111)、(III.01)+(15.112)。在这些结合物中,第一种组分为表III.1中所定义的式(III)的化合物(例如,III.01),而第二种组分为在本文中所定义的组1至15中所选择的杀真菌剂。例如,结合物(III.01)+(1.001)对应于包含表1中的化合物III.01和环唑醇(1.001)的结合物。
在一些其他实施方案中,化合物结合物对应于上述结合物,其中化合物(III.01)被表III.1中所提及的任一化合物所替换。
在这些结合物中,式(III)的化合物和选自组(1)至(15)的杀真菌剂可以100:1至1:100(式(III)的化合物:选自组(1)至(15)的杀真菌剂)或50:1至1:50,或20:1至1:20的重量比存在。重量比范围的其他实例包括95:1至1:95、90:1至1:90、85:1至1:85、80:1至1:80、75:1至1:75、70:1至1:70、65:1至1:65、60:1至1:60、55:1至1:55、45:1至1:45、40:1至1:40、35:1至1:35、30:1至1:30、25:1至1:25、15:1至1:15、10:1至1:10、5:1至1:5、4:1至1:4、3:1至1:3、2:1至1:2。
本发明的一种或多种化合物和组合物还可与一或多种生物防治剂结合。
可与本发明的一种或多种化合物和组合物结合的生物防治剂的实例为:
(A)选自以下的抗菌剂:
(A1)细菌,如(A1.1)枯草芽孢杆菌(Bacillus subtilis),特别是菌株QST713/AQ713(可从Bayer CropScience LP,US以SERENADE OPTI或SERENADE ASO得到,登记号为NRRL B21661且记载于美国专利第6,060,051号中);(A1.2)解淀粉芽孢杆菌(Bacillusamyloliquefaciens),特别是菌株D747(可从Certis,US以Double NickelTM得到,登记号为FERM BP-8234且记载于美国专利第7,094,592号中);(A1.3)短小芽孢杆菌(Bacilluspumilus),特别是菌株BU F-33(登记号为NRRL 50185);(A1.4)Bacillus subtilisvar.amyloliquefaciens菌株FZB24(可从Novozymes,US以得到);(A1.5)类芽孢杆菌属(Paenibacillus sp.)菌株,登记号为NRRL B-50972或登记号为NRRL B-67129,且记载于国际专利公开号WO 2016/154297中;以及
(A2)真菌,如(A2.1)出芽短梗霉菌(Aureobasidium pullulans),特别是菌株DSM14940的芽生孢子;(A2.2)菌株DSM 14941的出芽短梗霉菌芽生孢子;(A2.3)出芽短梗霉菌,特别是菌株DSM14940和DSM14941的芽生孢子的混合物;
(B)选自以下的杀真菌剂:
(B1)细菌,例如(B1.1)枯草芽孢杆菌,特别是菌株QST713/AQ713(可从BayerCropScience LP,US以SERENADE OPTI或SERENADE ASO得到,登记号NRRL B21661且记载于美国专利第6,060,051号中);(B1.2)短小芽孢杆菌,特别是菌株QST2808(可从BayerCropScience LP,US以得到,登记号NRRL B-30087且记载于美国专利第6,245,551号中);(B1.3)短小芽孢杆菌,特别是菌株GB34(可从Bayer AG,DE以Yield得到);(B1.4)短小芽孢杆菌,特别是菌株BU F-33(登记号NRRL50185);(B1.5)解淀粉芽孢杆菌,特别是菌株D747(可从Certis,US以Double NickelTM得到,登记号FERM BP-8234且公开于美国专利第7,094,592号中);(B1.6)枯草芽孢杆菌Y1336(可从中国台湾的Bion-Tech以WP得到,在中国台湾以登记号4764、5454、5096和5277登记为生物杀真菌剂);(B1.7)解淀粉芽孢杆菌菌株MBI 600(可从BASF SE以SUBTILEX得到);(B1.8)枯草芽孢杆菌菌株GB03(可从Bayer AG,DE以得到);(B1.9)Bacillus subtilisvar.amyloliquefaciens菌株FZB24(可从Novozymes Biologicals Inc.,Salem,Virginia或Syngenta Crop Protection,LLC,Greensboro,North Carolina以杀真菌剂或ECO(EPA登记号70127-5)得到);(B1.10)蕈状芽孢杆菌(Bacillus mycoides),分离物J(可从Certis USA以BmJ TGAI或WG得到);(B1.11)藓样芽胞杆菌(Bacillus licheniformis),特别是菌株SB3086(可从Novozymes以EcoGuard TMBiofungicide和Green Releaf得到);(B1.12)类芽孢杆菌属菌株,登记号为NRRL B-50972或登记号为NRRL B-67129,且记载于国际专利公开号WO 2016/154297中。
在一些实施方案中,生物防治剂为枯草芽孢杆菌或解淀粉芽孢杆菌菌株,其产生fengycin或plipastatin型化合物、伊枯草菌素型化合物和/或枯草菌表面活素型化合物。关于背景,参见以下综述文献:Ongena,M.,等人“Bacillus Lipopeptides:VersatileWeapons for Plant Disease Biocontrol,”Trends in Microbiology,第16卷,第3期,2008年3月,第115-125页。能产生脂肽的芽孢杆菌属菌株包括枯草芽孢杆菌QST713(可从Bayer CropScience LP,US以SERENADE OPTI或SERENADE ASO得到,登记号NRRL B21661且记载于美国专利第6,060,051号中),解淀粉芽孢杆菌菌株D747(可从Certis,US以DoubleNickelTM得到,登记号FERM BP-8234且公开于美国专利第7,094,592号中);枯草芽孢杆菌MBI600(可从Becker Underwood,US以得到,EPA登记号71840-8);枯草芽孢杆菌Y1336(可从中国台湾的Bion-Tech以WP得到,在中国台湾以登记号4764、5454、5096和5277登记为生物杀真菌剂);解淀粉芽孢杆菌,特别是菌株FZB42(可从ABiTEP,DE以得到);以及Bacillus subtilis var.amyloliquefaciens FZB24(可从Novozymes Biologicals Inc.,Salem,Virginia或Syngenta Crop Protection,LLC,Greensboro,North Carolina以杀真菌剂或ECO(EPA登记号70127-5)得到);和
(B2)真菌,例如:(B2.1)盾壳霉(Coniothyrium minitans),特别是菌株CON/M/91-8(登记号DSM-9660;例如购自Bayer的);(B2.2)核果梅奇酵母(Metschnikowia fructicola),特别是菌株NRRL Y-30752(例如);(B2.3)Microsphaeropsis ochracea(例如购自Prophyta的);(B2.5)木霉属(Trichoderma spp.),包括深绿木霉(Trichoderma atroviride),记载于国际申请号PCT/IT2008/000196中的菌株SC1;(B2.6)Trichoderma harzianum rifai菌株KRL-AG2(也称为菌株T-22,/ATCC 208479,例如购自BioWorks,US的PLANTSHIELD T-22G、和TurfShield);(B2.14)Gliocladium roseum,购自W.F.Stoneman Company LLC的菌株321U;(B2.35)黄色蠕形霉(Talaromyces flavus),菌株V117b;(B2.36)Trichodermaasperellum,购自Isagro的菌株ICC 012;(B2.37)Trichoderma asperellum,菌株SKT-1(例如购自Kumiai Chemical Industry的);(B2.38)深绿木霉(Trichodermaatroviride),菌株CNCM I-1237(例如购自Agrauxine,FR的WP);(B2.39)深绿木霉,菌株号V08/002387;(B2.40)深绿木霉,菌株NMI号V08/002388;(B2.41)深绿木霉,菌株NMI号V08/002389;(B2.42)深绿木霉,菌株NMI号V08/002390;(B2.43)深绿木霉,菌株LC52(例如由Agrimm Technologies Limited提供的Tenet);(B2.44)深绿木霉,菌株ATCC20476(IMI 206040);(B2.45)深绿木霉,菌株T11(IMI352941/CECT20498);(B2.46);Trichoderma harmatum;(B2.47)哈茨木霉(Trichoderma harzianum);(B2.48)哈茨木霉(Trichoderma harzianum rifai)T39(例如购自Makhteshim,US的);(B2.49)哈茨木霉,特别是菌株KD(例如购自Biological Control Products,SA的Trichoplus(由Becker Underwood获得));(B2.50)哈茨木霉,菌株ITEM 908(例如购自Koppert的Trianum-P);(B2.51)哈茨木霉,菌株TH35(例如由Mycontrol提供的Root-Pro);(B2.52)绿木霉(Trichoderma virens)(也称为绿粘帚霉(Gliocladium virens)),特别是菌株GL-21(例如由Certis,US提供的SoilGard 12G);(B2.53)绿色木霉(Trichodermaviride),菌株TV1(例如由Koppert提供的Trianum-P);(B2.54)白粉寄生孢(Ampelomycesquisqualis),特别是菌株AQ 10(例如由IntrachemBio Italia提供的AQ);(B2.56)出芽短梗霉菌,特别是菌株DSM14940的芽生孢子;(B2.57)出芽短梗霉菌,特别是菌株DSM14941的芽生孢子;(B2.58)出芽短梗霉菌,特别是菌株DSM14940和DSM 14941的芽生孢子的混合物(例如由bio-ferm,CH提供的);(B2.64)枝孢样枝孢霉(Cladosporiumcladosporioides),菌株H39(由Stichting Dienst Landbouwkundig Onderzoek提供);(B2.69)链孢粘帚霉(Gliocladium catenulatum)(同义词:Clonostachys roseaf.catenulate)菌株J1446(例如由AgBio Inc.提供的以及例如由Kemira AgroOy提供的);(B2.70)蜡蚧轮枝孢(Lecanicillium lecanii)(先前称为:Verticillium lecanii)菌株KV01的分生孢子(例如由Koppert/Arysta提供的);(B2.71)蠕形青霉(Penicillium vermiculatum);(B2.72)异常毕赤酵母(Pichiaanomala),菌株WRL-076(NRRL Y-30842);(B2.75)深绿木霉,菌株SKT-1(FERM P-16510);(B2.76)深绿木霉,菌株SKT-2(FERM P-16511);(B2.77)深绿木霉,菌株SKT-3(FERM P-17021);(B2.78)盖姆斯木霉(Trichoderma gamsii)(原名T.viride),菌株ICC080(IMI CC392151 CABI,例如由AGROBIOSOL DE MEXICO,S.A.DE C.V.提供的BioDerma);(B2.79)哈茨木霉,菌株DB 103(例如由Dagutat Biolab提供的T-Gro 7456);(B2.80)多孢木霉(Trichoderma polysporum),菌株IMI 206039(例如由BINAB Bio-Innovation AB,Sweden提供的Binab TF WP);(B2.81)Trichoderma stromaticum(例如由Ceplac,Brazil提供的Tricovab);(B2.83)Ulocladium oudemansii,特别是菌株HRU3(例如由Botry-Zen Ltd,NZ提供的);(B2.84)黑白轮枝孢(Verticillium albo-atrum)(原名V.dahliae),菌株WCS850(CBS 276.92;例如由Tree Care Innovations提供的DutchTrig);(B2.86)厚垣轮枝孢菌(Verticillium chlamydosporium);(B2.87)棘孢木霉(Trichoderma asperellum)菌株ICC 012和盖姆斯木霉菌株ICC 080的混合物(例如购自Bayer CropScience LP,US称为BIO-TAMTM的产品)。
可以与本发明的一种或多种化合物和组合物结合的生物防治剂的其他实例为:
选自以下的细菌:蜡状芽孢杆菌(Bacillus cereus),特别是蜡状芽孢杆菌(B.cereus)菌株CNCM I-1562和坚强芽胞杆菌(Bacillus firmus),菌株I-1582(登记号CNCM I-1582),枯草芽孢杆菌菌株OST 30002(登记号NRRL B-50421),苏云金芽孢杆菌(Bacillus thuringiensis),特别是苏云金芽孢杆菌以色列亚种(B.thuringiensissubspecies israelensis)(血清型H-14),菌株AM65-52(登记号ATCC 1276),苏云金芽孢杆菌鲇泽亚种(B.thuringiensis subsp.aizawai),特别是菌株ABTS-1857(SD-1372),苏云金芽孢杆菌库尔斯塔克亚种(B.thuringiensis subsp.kurstaki)菌株HD-1,苏云金芽孢杆菌拟步行甲亚种(B.thuringiensis subsp.tenebrionis)菌株NB 176(SD-5428),穿刺芽孢杆菌(Pasteuria penetrans),巴斯德氏芽菌属(Pasteuria spp.)(肾形线虫(Rotylenchulusreniformis nematode))-PR3(登记号ATCC SD-5834),细黄链霉菌(Streptomycesmicroflavus)菌株AQ6121(=QRD 31.013,NRRL B-50550),鲜黄链霉菌(Streptomycesgalbus)菌株AQ 6047(登记号NRRL 30232)。
选自以下的真菌和酵母:球孢白僵菌(Beauveria bassiana),特别是菌株ATCC74040;蜡蚧菌属(Lecanicillium spp.),特别是菌株HRO LEC 12;绿僵菌(Metarhiziumanisopliae),特别是菌株F52(DSM3884或ATCC 90448);玫烟色拟青霉(Paecilomycesfumosoroseus)(现名:玫烟色棒束孢(Isaria fumosorosea)),特别是菌株IFPC 200613或菌株Apopka 97(登记号ATCC 20874);和淡紫色拟青霉(Paecilomyces lilacinus),特别是淡紫色拟青霉菌株251(AGAL 89/030550);
选自以下的病毒:棉褐带卷蛾(Adoxophyes orana)(夏季水果卷叶蛾(summerfruit tortrix))颗粒体病毒(GV)、苹果蠹蛾(Cydia pomonella)(codling moth)颗粒体病毒(GV)、棉铃虫(Helicoverpa armigera)(cotton bollworm)核多角体病毒(NPV)、甜菜夜蛾(Spodoptera exigua)(beet armyworm)mNPV、草地贪夜蛾(Spodoptera frugiperda)(fall armyworm)mNPV和海灰翅夜蛾(Spodoptera littoralis)(非洲棉叶虫(Africancotton leafworm))NPV。
可以作为“接种剂(inoculant)”加入到植物或植物部位或植物器官并凭借其特定性能促进植物生长和植物健康的细菌和真菌。实例为:土壤杆菌属(Agrobacterium spp.),茎瘤固氮根瘤菌(Azorhizobium caulinodans),固氮螺菌属(Azospirillum spp.),固氮菌属(Azotobacter spp.),慢生根瘤菌属(Bradyrhizobium spp.),伯克霍尔德菌属(Burkholderia spp.),特别是洋葱伯克霍尔德菌(Burkholderia cepacia)(原名为洋葱假单胞菌(Pseudomonas cepacia)),巨孢囊霉属(Gigaspora spp.)或Gigasporamonosporum,球囊霉属(Glomus spp.),蜡蘑属(Laccaria spp.),布氏乳杆菌(Lactobacillus buchneri),类球囊霉属(Paraglomus spp.),Pisolithus tinctorus,假单胞菌属(Pseudomonas spp.),根瘤菌属(Rhizobium spp.),特别是三叶草根瘤菌(Rhizobium trifolii),须腹菌属(Rhizopogon spp.),硬皮马勃属(Scleroderma spp.),乳牛肝菌属(Suillus spp.)和链霉菌属(Streptomyces spp.)。
可用作生物防治剂的植物提取物和由微生物形成的产物(包括蛋白质和次生代谢物)为:例如,大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、Chenopodium anthelminticum、几丁质、Armour-Zen、欧洲鳞毛蕨(Dryopteris filix-mas)、问荆(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(藜麦皂苷提取物(Chenopodium quinoa saponin extract))、除虫菊(pyrethrum)/除虫菊酯(pyrethrins)、苏里南苦木(Quassia amara)、栎(Quercus)、皂树(Quillaja)、Regalia、"RequiemTM杀昆虫剂"、鱼藤酮(rotenone)、鱼尼丁(ryania)/兰尼碱(ryanodine)、聚合草(Symphytumofficinale)、菊蒿(Tanacetum vulgare)、百里酚(thymol)、Triact 70、TriCon、Tropaeulum majus、大荨麻(Urtica dioica)、藜芦碱(Veratrin)、白槲寄生(Viscumalbum)、十字花科(Brassicaceae)提取物(尤其是油菜籽粉末或芥末粉末)。
可各自地与本发明的一种或多种化合物和组合物混合的杀昆虫剂、杀螨剂和杀线虫剂的实例为:
(1)乙酰胆碱酯酶(AChE)抑制剂,例如氨基甲酸酯类,例如棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、灭除威(XMC)和灭杀威(xylylcarb),或有机磷酸酯类,例如乙酰甲胺磷(acephate)、甲基吡啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑膦(fosthiazate)、庚烯磷(heptenophos)、imicyafos、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯、异唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion)。
(2)GABA门控氯化物通道阻断剂,例如环戊二烯有机氯类,例如氯丹(chlordane)和硫丹(endosulfan),或苯基吡唑类(fiproles),例如乙虫腈(ethiprole)和氟虫腈(fipronil)。
(3)钠通道调节剂,例如拟除虫菊酯类(pyrethroids),例如氟丙菊酯(acrinathrin)、丙烯菊酯(allethrin)、d-顺式-反式丙烯菊酯、d-反式丙烯菊酯、联苯菊酯(bifenthrin)、生物丙烯菊酯(bioallethrin)、生物丙烯菊酯S-环戊烯基异构体、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯、三氟氯氰菊酯(cyhalothrin)、λ-三氟氯氰菊酯、γ-三氟氯氰菊酯、氯氰菊酯(cypermethrin)、α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、ζ-氯氰菊酯、苯醚氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-trans isomer])、溴氰菊酯(deltamethrin)、右旋烯炔菊酯[(EZ)-(1R)异构体](empenthrin[(EZ)-(1R)isomer])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、momfluorothrin、氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans isomer])、右旋炔丙菊酯(prallethrin)、除虫菊素(pyrethrins)(除虫菊(pyrethrum))、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(EZ)-(1R)异构体](tetramethrin[(EZ)-(1R)-isomer)])、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin),或滴滴涕(DDT),或甲氧滴滴涕(methoxychlor)。
(4)烟碱能乙酰胆碱受体(nAChR)竞争调节剂,例如新烟碱类(neonicotinoids),例如啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam),或烟碱(nicotine),或氟啶虫胺腈(sulfoxaflor),或氟吡呋喃酮(flupyradifurone)。
(5)烟碱能乙酰胆碱受体(nAChR)变构调节剂,例如多杀菌素类(spinosyns),例如乙基多杀菌素(spinetoram)和多杀菌素(spinosad)。
(6)谷氨酸酯门控氯化物通道(GluCl)变构调节剂,例如阿维菌素类(avermectins)/米尔倍霉素类(milbemycins),例如阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)和弥拜菌素(milbemectin)。
(7)保幼激素模拟物,例如保幼激素类似物,例如烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)和烯虫酯(methoprene),或苯氧威(fenoxycarb),或吡丙醚(pyriproxyfen)。
(8)其他非特异性(多位点)抑制剂,例如烷基卤化物类,例如甲基溴和其他烷基卤化物;或氯化苦(chloropicrine)或硫酰氟(sulphuryl fluoride)或硼砂(borax)或吐酒石(tartar emetic)或异氰酸甲酯生成剂,例如棉隆(diazomet)和威百亩(metam)。
(9)弦音器官(Chordotonal Organ)调节剂,例如吡蚜酮(pymetrozine)或氟啶虫酰胺(flonicamide)。
(10)螨生长抑制剂,例如四螨嗪(clofentezine)、噻螨酮(hexythiazox)和氟螨嗪(diflovidazin),或乙螨唑(etoxazole)。
(11)昆虫肠膜微生物干扰剂,例如苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis)和B.t植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/35Ab1。
(12)线粒体ATP合酶抑制剂,例如ATP干扰剂,例如丁醚脲(diafenthiuron),或有机锡化合物,例如三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatinoxide),或炔螨特(propargite),或四氯杀螨砜(tetradifon)。
(13)通过间断质子梯度的氧化磷酸化的解偶联剂,例如溴虫腈(chlorfenapyr)、二硝甲酚(DNOC)和氟虫胺(sulfluramid)。
(14)烟碱能乙酰胆碱受体通道阻断剂,例如杀虫磺(bensultap)、杀螟丹盐酸盐(cartap hydrochloride)、杀虫环(thiocyclam)和杀虫双(thiosultap-sodium)。
(15)0型几丁质生物合成抑制剂,例如双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、二氟脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀铃脲(triflumuron)。
(16)1型几丁质生物合成抑制剂,例如噻嗪酮(buprofezin)。
(17)蜕皮干扰剂(尤其是对于双翅目,即双翅类昆虫(dipterans)),例如灭蝇胺(cyromazine)。
(18)蜕皮激素受体激动剂,例如环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)。
(19)章鱼胺受体激动剂,例如双甲脒(amitraz)。
(20)线粒体复合物III电子传递抑制剂,例如氟蚁腙(hydramethylnone)或灭螨醌(acequinocyl)或嘧螨酯(fluacrypyrim)。
(21)线粒体复合物I电子传递抑制剂,例如METI杀螨剂类,例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)和唑虫酰胺(tolfenpyrad),或鱼藤酮(rotenone)(鱼藤属(Derris))。
(22)电压依赖型钠通道阻断剂,例如茚虫威(indoxacarb)或氰氟虫腙(metaflumizone)。
(23)乙酰基辅酶A(CoA)羧化酶抑制剂,例如特窗酸和特特拉姆酸(tetramicacid)衍生物,例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat)。
(24)线粒体复合物IV电子传递抑制剂,例如膦类,例如磷化铝、磷化钙、膦和磷化锌,或氰化物类,例如氰化钙、氰化钾和氰化钠。
(25)线粒体复合物II电子传递抑制剂,例如β-酮腈衍生物类(beta-keto nitrilederivatives),例如腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen)和甲酰苯胺类(carboxanilides),例如pyflubumide。
(28)兰尼碱(ryanodine)受体调节剂,例如二酰胺类,例如氯虫苯甲酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)和氟虫双酰胺(flubendiamide),
其他活性化合物,例如啶喃环丙虫酯(Afidopyropen)、阿福拉纳(Afoxolaner)、印楝素(Azadirachtin)、Benclothiaz、苯螨特(Benzoximate)、联苯肼酯(Bifenazate)、溴虫氟苯双酰胺(Broflanilide)、溴螨酯(Bromopropylate)、灭螨猛(Chinomethionat)、氯丙炔菊酯(chloroprallethrin)、冰晶石(Cryolite)、环溴虫酰胺(Cyclaniliprole)、环氧虫啶(Cycloxaprid)、氯氟氰虫酰胺(Cyhalodiamide)、Dicloromezotiaz、三氯杀螨醇(Dicofol)、ε-甲氧苄氟菊酯(Epsilon metofluthrin)、ε-Momfluthrin、Flometoquin、Fluazaindolizine、联氟砜(Fluensulfone)、嘧虫胺(Flufenerim)、氟菌螨酯(Flufenoxystrobin)、丁虫腈(Flufiprole)、Fluhexafon、氟吡菌酰胺(Fluopyram)、氟雷拉纳(Fluralaner)、Fluxametamide、呋喃虫酰肼(Fufenozide)、戊吡虫胍(Guadipyr)、Heptafluthrin、氯噻啉(Imidaclothiz)、异菌脲(Iprodione)、κ-联苯菊酯(kappa-Bifenthrin)、κ-七氟菊酯(kappa-Tefluthrin)、Lotilaner、氯氟醚菊酯(Meperfluthrin)、哌虫啶(Paichongding)、啶虫丙醚(Pyridalyl)、Pyrifluquinazon、嘧螨胺(Pyriminostrobin)、Spirobudiclofen、四氟醚菊酯(Tetramethylfluthrin)、氟氰虫酰胺(Tetraniliprole)、四氯虫酰胺(Tetrachlorantraniliprole)、Tiigolaner、Tioxazafen、硫氟肟醚(Thiofluoximate)、三氟苯嘧啶(Triflumezopyrim)和碘甲烷(iodomethane);其他基于坚强芽孢杆菌(Bacillus firmus)的制剂(I-1582,BioNeem,Votivo),和下列化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(由WO2006/043635获知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(由WO2003/106457获知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]异烟酰胺(由WO2006/003494获知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010052161获知)(CAS 1225292-17-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(由EP 2647626获知)(CAS-1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(由WO2004/099160获知)(CAS 792914-58-0)、PF1364(由JP2010/018586获知)(CAS 登记号1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(由WO2012/029672获知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-1,1,1-三氟-丙-2-酮(由WO2013/144213获知)(CAS 1461743-15-6)、N-[3-(苄基氨基甲酰基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲酰胺(由WO2010/051926获知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基氨基甲酰基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲酰胺(由CN103232431获知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异唑基]-2-甲基-N-(顺式-1-氧化-3-硫杂环丁基)苯甲酰胺、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异唑基]-2-甲基-N-(反式-1-氧化-3-硫杂环丁基)苯甲酰胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异唑基]-2-甲基-N-(顺式-1-氧化-3-硫杂环丁基)苯甲酰胺(由WO 2013/050317 A1获知)(CAS1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺(由WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1获知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]氨基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亚磺酰基]-1H-吡唑-3-甲腈(由CN 101337937 A获知)(CAS 1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基氨基)硫代甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺,(Liudaibenjiaxuanan,由CN 103109816 A获知)(CAS1232543-85-9);N-[4-氯-2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-甲酰胺(由WO 2012/034403A1获知)(CAS 1268277-22-0)、N-[2-(5-氨基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由WO 2011/085575 A1获知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)-嘧啶(由CN101337940 A获知)(CAS 1108184-52-6);(2E)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]肼甲酰胺和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]肼甲酰胺(由CN 101715774 A获知)(CAS1232543-85-9);3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯基-环丙烷甲酸酯(由CN 103524422 A获知)(CAS 1542271-46-4);(4aS)-7-氯-2,5-二氢-2-[[(甲氧基羰基)[4-[(三氟甲基)硫基]苯基]氨基]羰基]-茚并[1,2-e][1,3,4]二嗪-4a(3H)-甲酸甲酯(由CN 102391261 A获知)(CAS 1370358-69-2);6-脱氧-3-O-乙基-2,4-二-O-甲基1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]氨基甲酸酯]-α-L-吡喃甘露糖(由US 2014/0275503 A1获知)(CAS 1181213-14-8);8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 1253850-56-4)、(8-反式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 933798-27-7)、(8-顺式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(由WO 2007040280 A1、WO2007040282 A1获知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫基]丙酰胺(由WO 2015/058021 A1、WO 2015/058028 A1获知)(CAS 1477919-27-9)和N-[4-(氨基硫代甲基)-2-甲基-6-[(甲基氨基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由CN 103265527 A获知)(CAS 1452877-50-7)、5-(1,3-二氧杂环己烷-2-基)-4-[[4-(三氟甲基)苯基]甲氧基]-嘧啶(由WO 2013/115391 A1获知)(CAS 1449021-97-9)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1-甲基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010/066780 A1,WO 2011/151146 A1获知)(CAS1229023-34-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮杂螺[4.5]癸烷-2,4-二酮(由WO 2014/187846 A1获知)(CAS 1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基-碳酸乙酯(由WO 2010/066780 A1、WO 2011151146 A1获知)(CAS 1229023-00-0)、N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亚吡啶基]-2,2,2-三氟乙酰胺(由DE 3639877 A1、WO 2012029672 A1获知)(CAS1363400-41-2)、[N(E)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亚吡啶基]-2,2,2-三氟乙酰胺(由WO 2016005276 A1获知)(CAS 1689566-03-7)、[N(Z)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-亚吡啶基]-2,2,2-三氟乙酰胺(CAS 1702305-40-5)、3-内-3-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[[5-(三氟甲基)-2-吡啶基]氧基]-9-氮杂二环[3.3.1]壬烷(由WO2011/105506 A1、WO 2016/133011 A1获知)(CAS 1332838-17-1)。
可以与本发明的一种或多种化合物和组合物混合的安全剂的实例为例如解草嗪(benoxacor)、解毒喹(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草唑(furilazole)、双苯唑酸(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS 129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-唑烷(CAS 52836-31-4)。
可以与本发明的一种或多种化合物和组合物混合的除草剂的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚钠盐(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、禾草灭钠盐(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、4-氨基-3-氯-6-(4-氯-2-氟-3-甲基苯基)-5-氟吡啶-2-甲酸、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸钾盐(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆甲酯(bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyron)、甲羧除草醚(bifenox)、双丙氨膦(bialaphos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠盐(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴苯腈丁酸盐(bromoxynil-butyrate)、溴苯腈钾盐(bromoxynil-potassium)、溴苯腈庚酸盐(bromoxynil-heptanoate)和溴苯腈辛酸盐(bromoxynil-octanoate)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、氟唑草酮(carfentrazone),氟唑草酮乙酯(carfentrazone-ethyl)、草灭畏(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、伐草克钠盐(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯芴素(chlorflurenol)、氯芴素甲酯(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆乙酯(chlorimuron-ethyl)、氯酞酰亚胺(chlorophthalim)、绿麦隆(chlorotoluron)、氯酞酸甲酯(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、吲哚酮(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、异草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺酸(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyrimorate、环胺磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、cyhalofop、氰氟草酯(cyhalofop-butyl)、环丙津(cyprazine)、2,4-D、2,4-D-丁氧基乙基酯(2,4-D-butoyl)、2,4-D-丁基酯、2,4-D-二甲基铵、2,4-D-二醇胺、2,4-D-乙基酯、2,4-D-2-乙基己基酯、2,4-D-异丁基酯、2,4-D-异辛基酯、2,4-D-异丙基铵、2,4-D-钾、2,4-D-三异丙醇铵和2,4-D-三乙醇胺(2,4-D-trolamine)、2,4-DB、2,4-DB-丁基酯、2,4-DB-二甲基铵、2,4-DB-异辛基酯、2,4-DB-钾和2,4-DB-钠、杀草隆(daimuron(dymron))、茅草枯(dalapon)、棉隆(dazomet)、正癸醇、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏(dicamba)、敌草腈(dichlobenil)、2-(2,4-二氯苄基)-4,4-二甲基-1,2-唑烷-3-酮、2-(2,5-二氯苄基)-4,4-二甲基-1,2-唑烷-3-酮、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、精禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、二氟吡隆钠(diflufenzopyr-sodium)、唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、dimetrasulfuron、氨氟灵(dinitramine)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、敌草快(diquat)、二溴敌草快(diquat-dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆(ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氟乳醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、F-5231,即N-[2-氯-4-氟-5-[4-(3-氟丙基)-5-氧代-4,5-二氢-1H-四唑-1-基]苯基]乙磺酰胺,F-7967,即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、唑禾草灵(fenoxaprop)、精唑禾草灵(fenoxaprop-P)、唑禾草灵乙酯(fenoxaprop-ethyl)、精唑禾草灵乙酯(fenoxaprop-P-ethyl)、芬诺杀磺隆(fenoxasulfone)、fenquinotrione、四唑酰草胺(fentrazamide)、麦草氟(flamprop)、高效麦草氟异丙酯(flamprop-M-isopropyl)、高效麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟酮磺隆(flucarbazone)、氟酮磺隆钠盐(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、flufenpyr、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸戊酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、9-羟基芴甲酸(flurenol)、芴丁酯(flurenol-butyl)、芴二甲基铵(flurenol-dimethylammonium)、芴甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen),乙羧氟草醚乙酯(fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron),氟啶嘧磺隆甲酯钠盐(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸-甲基庚酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠盐(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、杀木膦(fosamine)、草铵膦(glufosinate)、草铵膦铵盐(glufosinate-ammonium)、精草铵膦钠盐(glufosinate-P-sodium)、精草铵膦铵盐(glufosinate-P-ammonium)、精草铵膦钠盐(glufosinate-P-sodium)、草甘膦(glyphosate)、草甘膦铵(glyphosate-ammonium)、草甘膦异丙基铵(glyphosate-isopropylammonium)、草甘膦二胺(glyphosate-diammonium)、草甘膦二甲基铵(glyphosate-dimethylammonium)、草甘膦钾(glyphosate-potassium)、草甘膦钠盐(glyphosate-sodium)、草甘膦三甲基锍盐(glyphosate-trimesium)、H-9201,即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基硫代磷酰胺酯(O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate)、氟氯吡啶酸(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯(haloxyfop-ethoxyethyl)、精氟吡禾灵乙氧基乙酯(haloxyfop-P-ethoxyethyl)、氟吡禾灵甲酯(haloxyfop-methyl)、精氟吡禾灵甲酯(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02,即乙基-(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)酯、咪草酸(imazamethabenz)、咪草酸甲酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵盐(imazamox-ammonium)、甲咪唑烟酸(imazapic),甲咪唑烟酸铵盐(imazapic-ammonium)、咪唑烟酸(imazapyr)、咪唑烟酸异丙铵(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaquin-ammonium)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸亚胺(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、碘苯腈辛酸酯(ioxynil-octanoate)、碘苯腈钾(ioxynil-potassium)和碘苯腈钠(ioxynil-sodium)、卤苯胺唑(ipfencarbazone)、异丙隆(isoproturon)、异隆(isouron)、异酰草胺(isoxaben)、异唑草酮(isoxaflutole)、特胺灵(karbutilate)、KUH-043,即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-唑、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙基酯(MCPA-butotyl)、MCPA-二甲基铵、MCPA-2-乙基己酯、MCPA-异丙基铵、MCPA-钾、MCPA-钠、MCPB、MCPB-甲酯、MCPB-乙酯、MCPB-钠、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠(mecoprop-sodium)、2-甲-4-氯丙酸丁氧基乙基酯(mecoprop-butotyl)、精2-甲-4-氯丙酸(mecoprop-P)、精2-甲-4-氯丙酸丁氧基乙基酯(mecoprop-P-butotyl)、精-2-甲-4-氯丙酸二甲基铵(mecoprop-P-dimethylammonium)、精-2-甲-4-氯丙酸-2-乙基己酯(mecoprop-P-2-ethylhexyl)、精-2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、二磺隆(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、甲基异硫氰酸酯、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、精异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)、MT-5950,即N-[3-氯-4-异丙基苯基]-2-甲基戊酰胺、NGGC-011、敌草胺(napropamide)、NC-310,即[5-苄氧基-1-甲基-1H-吡唑-4-基](2,4-二氯苯基)甲酮、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、壬酸(pelargonic acid)、氟草敏(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔草酮(oxadiargyl)、草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、嗪草酮(oxaziclomefon)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、二氯百草枯(paraquat dichloride)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚、环戊草酮(pentoxazone)、烯草胺(pethoxamid)、矿物油、苯敌草(phenmedipham)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆(primisulfuron-methyl)、氨氟乐灵(prodiamine)、环苯草酮(profoxydim)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠盐(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、pyraflufen,吡草醚(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、pyribambenz、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、pyriminobac、嘧草醚(pyriminobac-methyl)、pyrimisulfan、pyrithiobac、嘧草硫醚(pyrithiobac-sodium)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SL-261、磺草酮(sulcotrion)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249,即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯,SYP-300,即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮、2,3,6-TBA、TCA(三氯乙酸)、TCA-钠、丁噻隆(tebuthiuron)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、甲氧去草净(terbumeton)、特丁津(terbuthylazin)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、thiencarbazone、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野燕畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆母酸(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠盐(trifloxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲(urea sulfate)、灭草敌(vernolate)、XDE-848、ZJ-0862,即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺,以及以下化合物:
植物生长调节剂的实例为:
阿拉酸式苯(acibenzolar)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、5-氨基乙酰丙酸(5-aminolevolinic acid)、环丙嘧啶醇(ancymidol)、6-苄基氨基嘌呤(6-benzylaminopurine)、芸苔素内酯(Brassinolid)、儿茶酸(catechine)、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酰胺酸(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇、调呋酸(dikegulac)、调呋酸钠(dikegulac-sodium)、茵多酸(endothal)、茵多酸二钾(endothal-dipotassium)、茵多酸二钠(endothal-disodium)和茵多酸单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、9-羟基芴甲酸(flurenol)、芴丁酯(flurenol-butyl)、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸(indol-3-acetic acid(IAA))、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、烯丙苯噻唑(probenazole)、茉莉酸(jasmonic acid)、马来酸酰肼(maleic hydrazide)、甲哌啶(mepiquat chloride)、1-甲基环丙烯、茉莉酸甲基酯(methyljasmonate)、2-(1-萘基)乙酰胺、1-萘基乙酸、2-萘氧基乙酸、硝基苯酚盐混合物(nitrophenolate mixture)、多效唑(paclobutrazol)、N-(2-苯基乙基)-β-氨基丙酸、N-苯基邻氨甲酰苯甲酸(N-phenylphthalamic acid)、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、独角金内酯(strigolactone)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、trinexapac、抗倒酯(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)。
方法和用途
本发明的一种或多种化合物和组合物具有有效的植物防御调节潜力。它们可用于防治不想要的细菌,尤其是黄单胞菌属的细菌。本发明的一种或多种化合物和组合物可用于保护种子、发芽的种子、新发幼苗、植物、植物部位、果实、收获的物品和/或植物生长的土壤。
本文中所使用的防治(control或controlling)涵盖预防性、保护性、治疗性和根除性处理不想要的微生物。
因此,本发明涉及一种防治由黄单胞菌属的细菌所引起的细菌性病害的方法,其包括以下步骤:将至少一种本发明的化合物或至少一种本发明的组合物施用于植物、植物部位、种子、果实或植物生长的土壤。
通常,在将本发明的一种或多种化合物和组合物用在防治细菌性病害的治疗性或保护性方法中时,将它们以有效且与植物相容的量施用于植物、植物部位、果实、种子或植物生长的土壤或基质。可用于栽培植物的合适的基质包括无机基质,例如矿棉,尤其是石棉、珍珠岩、砂土或砾石;有机基质,例如泥炭、松树皮或锯末;以及基于石油的基质,例如聚合物泡沫或塑料珠。有效且与植物相容的量是指这样的量,其足以防治农田上存在或易于出现的细菌,并且不会引起所述作物产生任何明显的植物毒性症状。该量可以在较大范围内变化,这取决于要防治的病原体、作物类型、作物生长阶段、气候条件以及所使用的本发明的各个化合物或组合物。该量可以通过在本领域技术人员能力范围内的系统性田间试验确定。由细菌性病原体(例如,黄单胞菌属(例如,野油菜黄单胞菌水稻致病变种(Xanthomonas campestris pv.Oryzae))、假单胞菌属(例如,丁香假单胞菌甜瓜致病变种(Pseudomonas syringae pv.Lachrymans))、欧文属(例如,解淀粉欧文菌(Erwiniaamylovora)))所引起的病害可通过本发明的化合物来防治。式(III)的化合物还可有效地用于防治植物上的植物病原性真菌。
植物和植物部位
本发明的一种或多种化合物和组合物可以施用至任何植物或植物部位。
植物意指所有的植物和植物种群,例如想要和不想要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可以是可以通过常规育种和优化法或通过生物技术和基因工程方法或这些方法的结合而获得的植物,包括遗传修饰植物(GMO或转基因植物)以及受或不受植物育种权(plant breeders’rights)保护的植物栽培种。
遗传修饰植物(GMO)
遗传修饰植物(GMO或转基因植物)为异源基因被稳定地整合至基因组中的植物。术语“异源基因”主要意指这样的基因:在植物体外提供或组装,并且当其被引入细胞核、叶绿体或线粒体基因组时,该基因通过表达目的蛋白或多肽或通过下调或沉默其他存在于植物中的一种或多种基因(利用例如反义技术、共抑制技术、RNA干扰-RNAi-技术或microRNA-miRMA-技术)赋予转化植物新的或改进的农学特性或其他特性。位于基因组中的异源基因也称为转基因。由其在植物基因组中的具体位置定义的转基因称为转化株系或转基因株系。
植物栽培种应当理解为意指具有新特性(“性状”)并且已通过常规育种、诱变或重组DNA技术得到的植物。它们可为栽培种、变种、生物型或基因型。
植物部位应当理解为意指植物的地上和地下的所有部位和器官,如芽、叶、针叶、茎、干、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收材料以及无性和有性繁殖材料,例如插枝、块茎、根茎、分株及种子。
可根据本发明的方法处理的植物包括以下:棉花、亚麻、葡萄藤、水果、蔬菜,如蔷薇科属种(Rosaceae sp.)(例如仁果类,如苹果和梨,以及核果类,例如杏、樱桃、扁桃和桃,以及无核小果类,例如草莓)、Ribesioidae属种、胡桃科属种(Juglandaceae sp.)、桦木科属种(Betulaceae sp.)、漆树科属种(Anacardiaceae sp.)、壳斗科属种(Fagaceae sp.)、桑科属种(Moraceae sp.)、木犀科属种(Oleaceae sp.)、猕猴桃科属种(Actinidaceaesp.)、樟科属种(Lauraceae sp.)、芭蕉科属种(Musaceae sp.)(例如香蕉树和香蕉种植园)、茜草科属种(Rubiaceae sp.)(例如咖啡)、山茶科属种(Theaceae sp.)、梧桐科属种(Sterculiceae sp.)、芸香科属种(Rutaceae sp.)(例如柠檬、橙子和葡萄柚)、茄科属种(Solanaceae sp.)(例如番茄)、百合科属种(Liliaceae sp.)、紫菀科属种(Asteraceaesp.)(例如莴苣)、伞形科属种(Umbelliferae sp.)、十字花科属种(Cruciferae sp.)、藜科属种(Chenopodiaceae sp.)、葫芦科属种(Cucurbitaceae sp.)(例如黄瓜)、葱科属种(Alliaceae sp.)(例如韭葱、洋葱)、蝶形花科属种(Papilionaceae sp.)(例如豌豆);主要作物植物,如禾本科属种(Gramineae sp.)(例如玉米、草坪草、谷类(如小麦、黑麦、稻、大麦、燕麦、黍和黑小麦))、菊科属种(Asteraceae sp.)(例如向日葵)、十字花科属种(Brassicaceae sp.)(例如白球甘蓝、红球甘蓝、花茎甘蓝、花椰菜、抱子甘蓝、小白菜、球茎甘蓝、小红萝卜,以及油菜、芥菜、辣根和水芹)、豆科属种(Fabacae sp.)(例如菜豆、花生)、蝶形花科属种(Papilionaceae sp.)(例如大豆)、茄科属种(Solanaceae sp.)(例如马铃薯)、藜科属种(Chenopodiaceae sp.)(例如糖用甜菜、饲用甜菜、瑞士甜菜、甜菜根);园林和森林中的有用植物和观赏植物;以及这些植物各自的基因修饰品种。
可以通过上述公开的方法处理的植物和植物栽培种包括对一种或多种生物胁迫具有抗性的植物和植物栽培种,即所述植物对动物和微生物有害物(例如线虫、昆虫、螨类、植物病原性真菌、细菌、病毒和/或类病毒)具有更好的防御。
可以通过上述公开的方法处理的植物和植物栽培种包括那些对一种或多种非生物胁迫具有抗性的植物。非生物胁迫条件可包括例如干旱、低温暴露、热暴露、渗透胁迫、水涝、提高的土壤盐度、增强的矿物暴露、臭氧暴露、强光暴露、有限的氮营养素利用率、有限的磷营养素利用率、避荫。
可以通过上述公开的方法处理的植物和植物栽培种包括那些以提高的产量特性为特征的植物。所述植物中提高的产量可为以下因素的结果:例如,改良的植物生理机能、生长和发育,如水利用效率、持水效率、改善的氮利用率、增强的碳同化作用、改善的光合作用、提高的发芽率和加速的成熟。产量还可受到改进的植物体系结构(plantarchitecture)的影响(在胁迫和非胁迫条件下),所述植物体系结构包括但不限于:提早开花、对杂交种子生产的开花控制、幼苗活力、植株大小、节间数和节间距、根系生长、种子大小、果实大小、荚果大小、荚果数或穗数、每个荚果或穗的种子数量、种子质量、增强的种子饱满度、减少的种子散布、减少的荚开裂以及抗倒伏。其他的产量性状包括种子组成,如碳水化合物含量和组成,例如棉花或淀粉、蛋白质含量、油含量和组成、营养价值、抗营养化合物减少、改善的可加工性和更好的贮存稳定性。
可以通过上述公开的方法处理的植物和植物栽培种包括为杂交植物的植物和植物栽培种,该杂交植物已表达出杂种优势或杂交活力的特征,这通常导致更高的产量、活力、健康和对生物和非生物胁迫的抗性。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法例如基因工程而获得)包括这样的植物或植物栽培种,其为除草剂耐受性植物,即对一种或多种给定的除草剂具有耐受性的植物。这类植物可通过遗传转化或通过选择包含赋予这类除草剂耐受性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法例如基因工程获得)包括这样的植物或植物栽培种,其为昆虫抗性转基因植物,即对某些目标昆虫的侵袭具有抗性的植物。这类植物可通过遗传转化或通过选择包含赋予这类昆虫抗性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法例如基因工程获得)包括这样的植物或植物栽培种,其为病害抗性转基因植物,即对某些目标昆虫的侵袭具有抗性的植物。这类植物可通过遗传转化或通过选择包含赋予这类昆虫抗性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括对非生物胁迫具有耐受性的植物和植物栽培种。这类植物可通过遗传转化或通过选择包含赋予这类胁迫抗性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括这样的植物或植物栽培种,其显示出改变的采收产品的数量、质量和/或贮存稳定性,和/或改变的采收产品的特定成分的性质。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括具有改变的纤维特性的植物和植物栽培种,例如棉花植物。这类植物可通过遗传转化或通过选择包含赋予这类改变的纤维特性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括具有改变的油分布特性的植物和植物栽培种,例如油菜或相关的芸苔属(Brassica)植物。这类植物可通过遗传转化或通过选择包含赋予这类改变的油分布特性的突变的植物而获得。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括具有改变的种子落粒(shattering)特性的植物和植物栽培种,例如油菜或相关的芸苔属(Brassica)植物。这类植物可通过遗传转化或通过选择包含赋予这类改变的种子落粒特征的突变的植物而获得,且包括具有延迟或减少的种子落粒的植物,例如油菜植物。
可以通过上述公开的方法处理的植物和植物栽培种(通过植物生物技术方法如基因工程获得)包括具有改变的翻译后蛋白质修饰模式的植物和植物栽培种,例如烟草植株。
基于以下实施例可以进一步理解本发明教导的方面,所述实施例不应解释为以任何方式限制本发明的教导的范围。
实施例
制备实施例1:制备5-(4,5-二溴-3-氟-2-噻吩基)-6-氧杂-4-氮杂螺[2.4]庚-4-烯-7-酮(化合物III.01)
步骤1:制备1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.01)
向200mg(0.66mmol)的4,5-二溴-3-氟噻吩-2-甲酸和170mg(1.32mmol)的1-氨基环丙烷甲酸乙酯盐酸盐(1:1)溶解于3mL四氢呋喃中的溶液中添加0.14mL(1.00mmol)的三乙胺,随后添加0.59mL(1.00mmol)的50%(w/w)丙烷膦酸酐的乙酸乙酯溶液。将反应混合物在室温下搅拌2小时。将反应混合物用水淬灭并用乙酸乙酯萃取。将合并的有机层用硫酸镁干燥,过滤并在减压下浓缩。将残余物通过硅胶柱色谱(梯度正庚烷/乙酸乙酯)纯化,得到230mg(纯度83%,产率70%)的1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=3.15。(M+H)=414。
步骤2:制备1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸(化合物XXI.03)
向239mg(0.58mmol)的1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯溶解于3mL四氢呋喃中的溶液中滴加1.15mL的1M氢氧化锂水溶液(1.15mmol)。将反应物在室温下搅拌1小时。然后,将反应混合物在80℃下加热30分钟。将反应混合物用水稀释并小心地用1M盐酸水溶液酸化。用乙酸乙酯萃取水层。将合并的有机层用硫酸镁干燥,过滤并在减压下浓缩,得到158mg(纯度90%,产率64%)的1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸。LogP=2.15。(M+H)=408。
步骤3:制备5-(4,5-二溴-3-氟-2-噻吩基)-6-氧杂-4-氮杂螺[2.4]庚-4-烯-7-酮(化合物III.01)
向1.15g(2.97mmol)的1-{[(4,5-二溴-3-氟-2-噻吩基)羰基]氨基}环丙烷甲酸于50mL二氯甲烷中的悬浮液中添加几滴N,N-二甲基甲酰胺,随后添加0.31mL(3.57mmol)的草酰氯。将反应物在室温下搅拌1小时。将反应混合物用水淬灭并用二氯甲烷萃取。将合并的有机层用硫酸镁干燥,过滤并在减压下浓缩。将残余物通过硅胶柱色谱(梯度正庚烷/乙酸乙酯)纯化,得到270mg(纯度98%,产率23%)的5-(4,5-二溴-3-氟-2-噻吩基)-6-氧杂-4-氮杂螺[2.4]庚-4-烯-7-酮。LogP=3.58。(M+H)=368。
制备实施例2:制备中间体1-{[(4,5-二氯-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.11)
在惰性气氛下,在5mL微波小瓶中依次添加100mg(0.23mmol)的1-{[(4,5-二氯-3-碘-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.08)、21mg(0.34mmol)的甲基硼酸、2.6mg(0.01mmol)的乙酸钯(II)、6.5mg(0.02mmol)的三环己基膦和172mg(0.80mmol)的磷酸三钾,随后添加经脱气的甲苯(1.25mL)和水(0.13mL)。密封小瓶并将反应混合物在100℃下搅拌18小时。将反应混合物用水稀释并用二氯甲烷萃取。将合并的有机层经Chem ElutTM小柱过滤并在减压下浓缩。将残余物通过硅胶柱色谱(梯度正庚烷/乙酸乙酯)纯化,得到29mg(纯度100%,产率39%)的白色固体状的1-{[(4,5-二氯-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=3.16。(M+H)=322。
制备实施例3:制备中间体1-{[(3,4,5-三氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.05)
步骤1:制备1-{[(3-氨基-4,5-二氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXVIII.01)
向150mg(0.60mmol)的3-氨基-4,5-二氯噻吩-2-甲酸盐酸盐(1:1)(化合物XXXa.02)和255mg(1.50mmol)的1-氨基环丙烷甲酸乙酯盐酸盐(1:1)溶解于4.0mL二氯甲烷中的溶液中添加0.45mL(2.59mmol)的N,N-二异丙基乙胺,随后添加255mg(1.50mmol)的2-氯-1,3-二甲基咪唑鎓氯化物于2.0mL二氯甲烷中的溶液。将反应混合物在室温下搅拌16小时。将反应混合物用水淬灭并用二氯甲烷萃取。将合并的有机层用硫酸镁干燥,过滤并在减压下浓缩。将残余物通过制备型高效液相色谱(梯度乙腈/甲酸(1%)水溶液)纯化,得到69mg(纯度100%,产率35%)的白色固体状的1-{[(3-氨基-4,5-二氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=2.77。(M+H)=323。
步骤2:制备1-{[(3,4,5-三氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.05)
在0℃下,向氯化亚铜(I)(9.8mg,0.10mmol)于0.5mL无水乙腈中的溶液中滴加亚硝酸叔丁酯(13μL,0.10mmol)。将反应混合物升温至室温,然后滴加25mg(0.06mmol)的1-{[(3-氨基-4,5-二氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯于0.5mL无水乙腈中的溶液。将反应混合物在室温下搅拌3小时。将反应混合物用二氯甲烷稀释并小心地用1M盐酸水溶液酸化。将水层用二氯甲烷萃取两次。将合并的有机层用硫酸镁干燥,过滤并在减压下浓缩。将残余物通过制备型高效液相色谱(梯度乙腈/甲酸(1%)水溶液)纯化,得到12mg(纯度93%,产率48%)的米色固体状的1-{[(3,4,5-三氯-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=3.40。(M)=341。
制备实施例4:制备中间体1-{[(4,5-二溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.02)
步骤1:制备1-[({4-溴-5-[(叔丁氧基羰基)氨基]-3-甲基-2-噻吩基}羰基)氨基]环丙烷甲酸乙酯(化合物XXVa.01)
向92mg(0.27mmol)的4-溴-5-[(叔丁氧基羰基)氨基]-3-甲基噻吩-2-甲酸(化合物XXVIIa.02)和67mg(0.41mmol)的1-氨基环丙烷甲酸乙酯盐酸盐溶于1.4mL二氯甲烷中的溶液中添加0.14mL(0.82mmol)的N,N-二异丙基乙胺,随后添加135mg(0.35mmol)的1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸盐。将反应混合物在室温下搅拌3.5小时。将反应混合物用水淬灭并用二氯甲烷萃取。将合并的有机层经Chem ElutTM小柱过滤并在减压下浓缩。通过硅胶柱色谱(梯度正庚烷/乙酸乙酯)纯化残余物,得到95mg(纯度93%,产率72%)的橙色固体状的1-[({4-溴-5-[(叔丁氧基羰基)氨基]-3-甲基-2-噻吩基}羰基)氨基]环丙烷甲酸乙酯。LogP=3.28。(M+H)=447。
步骤2:制备1-{[(5-氨基-4-溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXIVa.01)
向60mg(0.13mmol)的1-[(叔丁氧基羰基)氨基]-3-甲基-2-噻吩基}羰基)氨基]环丙烷甲酸酯于0.60mL氯仿中的溶液中添加0.62mL三氟乙酸。将反应物在室温下搅拌18小时。将反应混合物用甲苯稀释并在减压下浓缩。通过制备型高效液相色谱(梯度乙腈/乙酸铵(1mM)水溶液)纯化残余物,得到35mg(纯度100%,产率74%)的白色固体状的1-{[(5-氨基-4-溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=1.92。(M+H)=347。
步骤3:制备1-{[(4,5-二溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯(化合物XXI.02)
在0℃下,向溴化铜(II)(28.9mg,0.13mmol)于0.5mL无水乙腈中的溶液中滴加亚硝酸叔丁酯(17μL,0.13mmol)。使反应混合物升温至室温,然后滴加30mg(0.08mmol)的1-{[(5-氨基-4-溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯于0.7mL无水乙腈中的溶液。将反应混合物在室温下搅拌2小时。将反应混合物用乙酸乙酯稀释并小心地用1M盐酸水溶液酸化。用乙酸乙酯萃取水层三次。合并的有机层用硫酸镁干燥,过滤并在减压下浓缩。通过硅胶柱色谱(梯度正庚烷/乙酸乙酯)纯化残余物,得到11mg(纯度100%,产率31%)的白色固体状的1-{[(4,5-二溴-3-甲基-2-噻吩基)羰基]氨基}环丙烷甲酸乙酯。LogP=3.19。(M+H)=410。
示例性化合物
表III.1、III.2、III.3、III.4、III.5、III.6和III.7中所示的本发明的化合物以类似于上文所提供的实施例和/或根据本文中所公开方法的一般性描述来制备。
下表III.1以非限制性方式说明式(III)的化合物的实施例。
表III.1:
实施例编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | LogP |
III.01 | Br | Br | F | 3.57<sup>[a]</sup> |
III.02 | Br | Br | Me | 4.33<sup>[a]</sup> |
III.03 | Cl | Cl | Cl | 4.01<sup>[a]</sup> |
III.04 | Cl | Cl | Me | 4.30<sup>[a]</sup> |
III.05 | Br | Br | I | 4.30<sup>[a]</sup> |
III.06 | Br | Br | Br | 4.15<sup>[a]</sup> |
III.07 | Cl | Cl | Br | 4.12<sup>[a]</sup> |
III.08 | Br | Br | Cl | 4.08<sup>[a]</sup> |
III.09 | Cl | Cl | I | 4.23<sup>[a]</sup> |
注:Me:甲基
下表中所示的本发明的中间体以类似于上文所提供的实施例和/或根据本文中所公开方法的一般性说明来制备。
下表III.2以非限制性方式说明式(XXI)的中间体的实施例。
表III.2:
实施例编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | LogP |
XXI.01 | Br | Br | F | Et | 3.17<sup>[a]</sup> |
XXI.02 | Br | Br | Me | Et | 3.22<sup>[a]</sup> |
XXI.03 | Br | Br | F | H | 2.14<sup>[a]</sup> |
XXI.04 | Br | Br | Me | H | 2.25<sup>[a]</sup> |
XXI.05 | Cl | Cl | Cl | Et | 3.41<sup>[a]</sup> |
XXI.06 | Cl | Cl | Cl | H | 2.06<sup>[a]</sup> |
XXI.07 | Cl | Cl | Br | Et | 3.45<sup>[a]</sup> |
XXI.08 | Cl | Cl | I | Et | 3.39<sup>[a]</sup> |
XXI.09 | Cl | Cl | I | H | 2.34<sup>[a]</sup> |
XXI.10 | Br | Br | I | Et | 3.41<sup>[a]</sup> |
XXI.11 | Cl | Cl | Me | Et | 3.16<sup>[a]</sup> |
XXI.12 | Cl | Cl | Me | Me | 2.75<sup>[a]</sup> |
XXI.13 | Br | Br | I | Me | 3.06<sup>[a]</sup> |
XXI.14 | Cl | Cl | Me | H | 2.17<sup>[a]</sup> |
XXI.15 | Br | Br | I | H | 2.43<sup>[a]</sup> |
XXI.16 | Br | Br | Cl | Et | 3.51<sup>[a]</sup> |
XXI.17 | Br | Br | Cl | Me | 3.06<sup>[a]</sup> |
XXI.18 | Br | Br | Br | Me | 3.11<sup>[a]</sup> |
XXI.19 | Cl | Cl | Br | Me | 3.06<sup>[a]</sup> |
XXI.20 | Br | Br | Cl | H | 2.41<sup>[a]</sup> |
XXI.21 | Br | Br | Br | H | 2.43<sup>[a]</sup> |
XXI.22 | Cl | Cl | Br | H | 2.37<sup>[a]</sup> |
XXI.23 | Cl | Cl | Cl | Me | 3.04<sup>[a]</sup> |
XXI.24 | Br | Br | F | Me | 2.77<sup>[a]</sup> |
XXI.25 | Br | Br | Me | Me | 2.86<sup>[a]</sup> |
注:Me:甲基,Et:乙基
下表III.3以非限制性方式说明式(XXIIa)的中间体的实施例。
表III.3:
实施例编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | U<sup>1a</sup> | LogP |
XXIIa.01 | Cl | Cl | Br | OEt | 4.58<sup>[a]</sup> |
XXIIa.02 | Br | Br | I | OEt | 4.78<sup>[a]</sup> |
XXIIa.03 | Cl | Cl | I | OH | 2.64<sup>[a]</sup> |
XXIIa.04 | Cl | Cl | I | OMe | 4.15<sup>[a]</sup> |
XXIIa.05 | Br | Br | I | OMe | 4.20<sup>[a]</sup> |
XXIIa.06 | Cl | Cl | Br | OH | 2.52<sup>[a]</sup> |
XXIIa.07 | Cl | Cl | I | OEt | 4.73<sup>[b]</sup> |
XXIIa.08 | Br | Br | F | 2-甲基丙氧基 | 5.31<sup>[a]</sup> |
XXIIa.09 | Cl | Cl | Br | OMe | 4.11<sup>[a]</sup> |
XXIIa.10 | Br | Br | Me | 2-甲基丙氧基 | 6.12<sup>[a]</sup> |
XXIIa.11 | Cl | Cl | Me | OEt | 4.80<sup>[a]</sup> |
XXIIa.12 | Cl | Cl | Me | 2-甲基丙氧基 | 6.05<sup>[a]</sup> |
XXIIa.13 | Cl | Cl | Cl | 2-甲基丙氧基 | 5.75<sup>[a]</sup> |
注:Me:甲基
下表III.4以非限制性方式说明式(XXIVa)和(XXVa)的中间体的实施例。
表III.4:
实施例编号 | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | V | LogP |
XXIVa.01 | Br | Me | Et | 1.97<sup>[a]</sup> | |
XXVa.01 | Br | Me | Et | 叔丁氧基羰基 | 3.44<sup>[b]</sup> |
注:Et:乙基
下表III.5以非限制性方式说明式(XXVIIa)的中间体的实施例。
表III.5:
实施例编号 | R<sup>2</sup> | R<sup>3</sup> | U<sup>1a</sup> | V | LogP |
XXVIIa.01 | Br | Me | OEt | 叔丁氧基羰基 | 4.62<sup>[a]</sup> |
XXVIIa.02 | Br | Me | OH | 叔丁氧基羰基 | 2.86<sup>[a]</sup> |
注:Me:甲基,Et:乙基
下表III.6以非限制性方式说明式(XXVIII)和(XXIXa)的中间体的实施例。
表III.6:
实施例编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>4</sup> | V | LogP |
XXVIII.01 | Cl | Cl | Et | 2.77<sup>[a]</sup> | |
XXIXa.01 | Cl | Cl | Et | 叔丁氧基羰基 | 3.34<sup>[a]</sup> |
注:Et:乙基
下表III.7以非限制性方式说明式(XXXa)和(XXXIa)中间体的实施例。
表III.7:
实施例编号 | R<sup>1</sup> | R<sup>2</sup> | U<sup>1a</sup> | V | LogP |
XXXa.01 | Br | Br | OMe | - | 3.15<sup>[a]</sup> |
XXXa.02 | Cl | Cl | OH | - | 2.05<sup>[a]</sup> |
XXXIa.01 | Br | Br | OMe | 乙酰基 | 2.01<sup>[a]</sup> |
XXXIa.02 | Br | Br | OH | 乙酰基 | 1.39<sup>[a]</sup> |
注:Me:甲基;乙酰基:-C(=O)-CH3
在上表中,根据EEC directive 79/831 Annex V.A8,通过HPLC(高效液相色谱)在反相柱上使用下述方法进行LogP值的测量:
[a]LogP值通过在酸性范围内使用0.1%甲酸水溶液和乙腈作为洗脱液(线性梯度为10%乙腈至95%乙腈)进行LC-UV测量而确定。
[b]LogP值通过在中性范围内使用0.001摩尔乙酸铵水溶液和乙腈作为洗脱液(线性梯度为10%乙腈至95%乙腈)进行LC-UV测量而确定。
[c]LogP值通过在酸性范围内使用0.1%磷酸和乙腈作为洗脱液(线性梯度为10%乙腈至95%乙腈)进行LC-UV测量而确定。
如果在同一方法内,可获得多于一个LogP值,则示出所有的值并且以“+”分开。
使用具有已知LogP值的直链烷-2-酮(具有3至16个碳原子)进行校准(LogP值的测量通过在连续的烷酮之间的线性内插法使用保留时间进行)。使用200nm至400nm的UV光谱和色谱信号的峰值测定λmax值。
NMR-峰列表
表A提供了上表所公开的一些化合物的NMR数据(1H)。
所选实施例的1H-NMR数据以1H-NMR峰列表的形式示出。对于各信号峰,列出了以ppm计的δ值,并且在圆括号内列出了信号强度。在δ值-信号强度数对之间以分号分隔列出。
因此,一个实例的峰值列表采用以下形式:
δ1(强度1);δ2(强度2);........;δi(强度i);........;δn(强度n)
尖锐信号的强度与以厘米计的NMR光谱的打印实例的信号的高度相关,并且示出信号强度的真实关系。由宽信号可以示出多个峰或信号中部以及其与光谱中最强信号相比的相对强度。
为校准1H谱的化学位移,利用四甲基硅烷和/或所用溶剂的化学位移,特别是在DMSO中测量的光谱的情况下。因此,在NMR峰列表中,四甲基硅烷峰可以但不是必需出现。
1H-NMR峰的列表类似于常规1H-NMR打印件,因此,其通常含有以常规NMR说明列出的所有峰。
另外,如同常规1H-NMR打印件,其可显示出溶剂信号、目标化合物的立体异构体(其也是本发明的主题)的信号和/或杂质峰的信号。
为了示出在溶剂和/或水的δ范围内的化合物信号,溶剂的常规峰,例如在DMSO-D6中的DMSO的峰和水的峰示于1H-NMR峰列表中,并且通常具有平均的高强度。
目标化合物的立体异构体的峰和/或杂质的峰通常具有比目标化合物(例如具有>90%的纯度)的峰平均更低的强度。
这些立体异构体和/或杂质对于特定制备方法可以是典型的。因此,它们的峰可借助“副产品指纹图谱”帮助识别制备方法的再现性。
技术人员在使用已知方法(MestreC,ACD模拟,以及利用凭经验评估的预期值)计算目标化合物的峰时,可以任选地使用附加的强度滤波器按照需要分离出目标化合物的峰。这种分离类似于常规1H-NMR说明中相关峰的拾取。
带有峰列表的NMR数据说明的其他详情可见于研究公开数据库第564025号(Research Disclosure Database Number 564025)的出版物“Citation of NMR PeaklistData within Patent Applications”。
表A:NMR峰列表
生物数据
实施例A:野油菜黄单胞菌野油菜致病变种的体外细胞测试
溶剂:DMSO
培养基:LB肉汤培养基(Luria Broth Miller)Sigma
接种物:细菌悬浮液
将待测试的化合物溶解于DMSO,并且将溶液用于制备所需的浓度范围。在测试中使用的DMSO的最终浓度为≤1%。
接种物由在液体培养基中生长的细菌的预培养物制备,并稀释至所需的光密度(OD)。
在液体培养物测试中,评估化合物抑制细菌生长的能力。将化合物以所需浓度添加至含有细菌悬浮液的培养基中。在温育24h之后,通过光谱法测量细菌生长以测定化合物的功效。通过将在含有化合物的孔中的吸光度与在不含化合物的对照孔中的吸光度进行比较来测定抑制性。
在此测试中,本发明的以下化合物在20ppm的所测试化合物浓度下不显示出直接的活性:III.01;III.02;III.03;III.04;III.05。
实施例B:野油菜黄单胞菌野油菜致病变种(甘蓝菜上的黑腐病)的体内预防性测
试
在72小时之后,通过用野油菜黄单胞菌野油菜致病变种的水性细菌悬浮液喷洒叶片来侵染植物。将受侵染的甘蓝菜植物在27℃和95%相对湿度下培育8或10天。
在接种后8或10天评估测试。0%意指相当于对照植物的功效,而100%的功效意指未观测到病害。
在该测试中,本发明的以下化合物在31ppm的所测试化合物浓度下显示出至少60%的功效*:III.01;III.03;III.04;III.08;III.09。
在该测试中,本发明的以下化合物在125ppm的所测试化合物浓度下显示出至少60%的功效*:III.01;III.0 4;III.05;III.06;III.08;III.09。
*若干测试的算术平均值
实施例C:比较实施例
在与实施例B中所述相同的条件下,将化合物CMP5在野油菜黄单胞菌野油菜致病变种(甘蓝菜的黑腐病)的体内预防性试验中进行测试。
根据WO 2004/062361的教导来制备化合物CMP5。
结果如下表所示。
*4次测试的算术平均值
本发明的式(III)的化合物在31ppm或125ppm的浓度下测试时,显示出比结构上相关的化合物CMP5更好的功效。
更具体而言,化合物III.01、III.03、III.04、III.08和III.09在31ppm的浓度下显示出至少60%的功效,而CMP5在相同浓度下显示出小于40%的功效。
化合物III.01、III.04、III.05、III.06、III.08和III.09在125ppm的浓度下显示出至少60%的功效,而CMP5在相同浓度下显示出小于40%的功效。
Claims (15)
2.根据权利要求1所述的式(III)的化合物,其中R3为氟原子、氯原子或甲基。
3.根据权利要求1所述的式(III)的化合物,其中R3与R1和R2不同。
4.组合物,其包含至少一种前述权利要求中任一项所述的式(III)的化合物和至少一种农业上合适的助剂。
5.一种防治细菌性病害的方法,其包括以下步骤:将至少一种根据权利要求1至3中任一项所述的式(III)的化合物或根据权利要求4所述的组合物施用至植物、植物部位、种子、果实或植物生长的土壤。
12.式(XXIIa)的化合物:
其中
R1和R2为相同的且为溴原子或氯原子;
R3为氟原子、氯原子、溴原子、碘原子或甲基;并且
U1a为羟基或C1-C6-烷氧基;
条件是当R1和R2为氯原子时,R3不为氯原子;并且
条件是式(XXIIa)的化合物不表示:
4,5-二氯-3-氟噻吩-2-甲酸甲酯[2166596-88-7],
4,5-二氯-3-氟噻吩-2-甲酸[2166596-87-6],
4,5-二溴-3-氟噻吩-2-甲酸乙酯[2260624-98-2],
4,5-二溴-3-氟噻吩-2-甲酸[1628447-64-2],
4,5-二溴-3-氯噻吩-2-甲酸甲酯[1501789-47-4],
4,5-二溴-3-碘噻吩-2-甲酸[854626-46-3],
4,5-二溴-3-氯噻吩-2-甲酸[503308-99-4],
4,5-二溴-3-氯噻吩-2-甲酸乙酯[503308-98-3],
4,5-二溴-3-氟噻吩-2-甲酸甲酯[395664-58-1],
3,4,5-三溴噻吩-2-甲酸叔丁酯[62224-27-5],
3,4,5-三溴噻吩-2-甲酸乙酯[54113-44-9],
3,4,5-三溴噻吩-2-甲酸[53317-05-8],
3,4,5-三溴噻吩-2-甲酸甲酯[24647-80-1],
4,5-二溴-3-甲基噻吩-2-甲酸乙酯[2088257-63-8],
4,5-二氯-3-甲基噻吩-2-甲酸[854626-34-9],
4,5-二溴-3-甲基噻吩-2-甲酸[854626-32-7],
4,5-二氯-3-甲基噻吩-2-甲酸甲酯[854626-27-0],和
4,5-二溴-3-甲基噻吩-2-甲酸甲酯[648412-53-7]。
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