CN115232083A - Substituted isoxazolyl ethylamine compounds and preparation method and application thereof - Google Patents
Substituted isoxazolyl ethylamine compounds and preparation method and application thereof Download PDFInfo
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- CN115232083A CN115232083A CN202110435945.6A CN202110435945A CN115232083A CN 115232083 A CN115232083 A CN 115232083A CN 202110435945 A CN202110435945 A CN 202110435945A CN 115232083 A CN115232083 A CN 115232083A
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- radical
- halo
- alkyl
- alkoxy
- group
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- 238000002360 preparation method Methods 0.000 title claims description 16
- YJPOJVOMWRNRQR-UHFFFAOYSA-N n-ethyl-1,2-oxazol-3-amine Chemical class CCNC=1C=CON=1 YJPOJVOMWRNRQR-UHFFFAOYSA-N 0.000 title description 2
- -1 isoxazolyl ethylamine compound Chemical class 0.000 claims abstract description 159
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 125000001424 substituent group Chemical group 0.000 claims abstract description 86
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims description 332
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 10
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 4
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- GJHDTCHKZVZFHR-UHFFFAOYSA-N 2-(1,2-oxazol-3-yl)ethanamine Chemical class NCCC=1C=CON=1 GJHDTCHKZVZFHR-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 25
- 241000233679 Peronosporaceae Species 0.000 abstract description 24
- 241000221785 Erysiphales Species 0.000 abstract description 21
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 20
- 240000008067 Cucumis sativus Species 0.000 abstract description 15
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 15
- 240000008042 Zea mays Species 0.000 abstract description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 7
- 235000005822 corn Nutrition 0.000 abstract description 7
- 240000007594 Oryza sativa Species 0.000 abstract description 6
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 6
- 235000009566 rice Nutrition 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 35
- 201000010099 disease Diseases 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 241000221662 Sclerotinia Species 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 241000209140 Triticum Species 0.000 description 13
- 235000021307 Triticum Nutrition 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 206010027146 Melanoderma Diseases 0.000 description 10
- 244000052616 bacterial pathogen Species 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000219112 Cucumis Species 0.000 description 8
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 8
- 241000918585 Pythium aphanidermatum Species 0.000 description 8
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 235000002566 Capsicum Nutrition 0.000 description 7
- 239000006002 Pepper Substances 0.000 description 7
- 244000046052 Phaseolus vulgaris Species 0.000 description 7
- 235000016761 Piper aduncum Nutrition 0.000 description 7
- 240000003889 Piper guineense Species 0.000 description 7
- 235000017804 Piper guineense Nutrition 0.000 description 7
- 235000008184 Piper nigrum Nutrition 0.000 description 7
- 235000002597 Solanum melongena Nutrition 0.000 description 7
- 244000061458 Solanum melongena Species 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
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- 244000036905 Benincasa cerifera Species 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- QKWBTCRVPQHOMT-UITAMQMPSA-N (nz)-n-[(4-chlorophenyl)methylidene]hydroxylamine Chemical compound O\N=C/C1=CC=C(Cl)C=C1 QKWBTCRVPQHOMT-UITAMQMPSA-N 0.000 description 5
- VHNZPGONQZTTKQ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1,2-oxazol-5-yl]ethanamine Chemical compound O1C(CCN)=CC(C=2C=CC(Cl)=CC=2)=N1 VHNZPGONQZTTKQ-UHFFFAOYSA-N 0.000 description 5
- 240000007087 Apium graveolens Species 0.000 description 5
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
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- 230000001276 controlling effect Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
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- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002633 protecting effect Effects 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- PZBPHYLKIMOZPR-FIYGWYQWSA-K 2-[4-[2-[[(2r)-1-[[(4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-4-[[(2r,3r)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1r)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl] Chemical compound [68Ga+3].C([C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)NC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1)C1=CC=CC=C1 PZBPHYLKIMOZPR-FIYGWYQWSA-K 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000533770 Cayaponia Species 0.000 description 1
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- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 241001272202 Phoma destructiva var. destructiva Species 0.000 description 1
- 241000907661 Pieris rapae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241001638069 Rigidoporus microporus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
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- 235000004611 garlic Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004992 haloalkylamino group Chemical group 0.000 description 1
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000005292 haloalkynyloxy group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/80—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 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses a substituted isoxazolyl ethylamine compound, which has a structure shown as a general formula I; the definition of each substituent group in the formula is shown in the specification. The compound has broad-spectrum bactericidal activity and has excellent control effects on cucumber downy mildew, powdery mildew, corn rust, anthracnose, rice blast and the like.
Description
Technical Field
The invention belongs to the field of chemistry, and particularly relates to a substituted isoxazole ethylamine compound, a preparation method thereof and application thereof as a bactericide.
Background
The Bioorganic & Medicinal Chemistry (2015), 23 (6), 1260-1275 and WO 9219604 disclose substituted isoxazolylethylamines, the use of which is in the medical field, as receptor antagonists and lipoxygenase and cyclooxygenase inhibitors, respectively.
Although the compounds disclosed in the prior art have certain similarities with the compounds disclosed by the invention, the compounds shown by the general formula of the invention are obviously different from the prior art, and have good bactericidal activity.
Disclosure of Invention
The invention aims to provide a substituted isoxazolyl ethylamine compound capable of controlling various pathogenic bacteria, a preparation method thereof and application of the substituted isoxazolyl ethylamine compound in preparation of medicines for preventing and treating pathogenic bacteria in agriculture or other fields.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a substituted isoxazole ethylamine compound is characterized in that: the substituted isoxazole ethylamine compound is a compound shown as a general formula I;
in the formula:
R 1 selected from hydrogen, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkynyl, C 3 -C 12 Alkenyloxy, halogeno C 3 -C 12 Alkenyloxy radical, C 3 -C 12 Alkynyloxy, halo C 3 -C 12 Alkynyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl or C 1 -C 12 Alkylthio group C 1 -C 12 An alkyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, di (halo C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkylthio, halo C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogeno C 2 -C 12 Alkenyloxy radical, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkylcarbonyl group, C 1 -C 12 Alkoxycarbonyl, halogeno C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylcarbonyloxy, halo C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo C 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo C 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy or halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer of 0 to 5, and when n is 0, no substituent is provided; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkynyl, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylsulfinyl, halogeno C 1 -C 12 Alkylsulfinyl radical, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylaminosulfonyl, di (C) 1 -C 12 Alkyl) aminosulfonyl, C 1 -C 12 Alkylsulfonylaminocarbonyl group, C 1 -C 12 Alkylcarbonylaminosulfonyl radical, C 3 -C 12 Cycloalkyloxycarbonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkyl carbonyl, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkyl carbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylaminocarbonyl, di (C) 1 -C 12 Alkyl) aminocarbonyl, C 2 -C 12 Alkenyloxycarbonyl radical, C 2 -C 12 Alkynyloxycarbonyl, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxycarbonyl, arylcarbonyl C which is unsubstituted or substituted by 1 to 5 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C 1 -C 6 Alkyloxycarbonyl, aryl C 1 -C 6 Alkyl, heteroaryl carbonyl C 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C 1 -C 6 Alkyloxycarbonyl, heteroaryl C 1 -C 6 Alkyl, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 4 、R 5 C connected thereto may also form C 3 -C 8 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 6 、R 7 C connected thereto may also form C 3 -C 8 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted aryl, heteroaryl.
R 8 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, halo-di (C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkylthio, halo C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogeno C 2 -C 12 Alkenyloxy radical, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkylcarbonyl group, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylcarbonyloxy, halo C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo C 1 -C 12 Alkoxy carbonyl oxygen radical、C 1 -C 12 Alkylsulfonyloxy, halo C 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy or halo C 1 -C 12 Alkoxy radical C 1 -C 12 An alkoxy group.
Preferably, in the compound of formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl, C 3 -C 6 Alkenyloxy, halogeno C 3 -C 6 Alkenyloxy radical, C 3 -C 6 Alkynyloxy, halo C 3 -C 6 Alkynyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl or C 1 -C 6 Alkylthio C 1 -C 6 An alkyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, di (halo C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkylthio, halo C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogeno C 2 -C 6 Alkenyloxy radical, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkyl carbonyl, C 1 -C 6 Alkoxycarbonyl, halogeno C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylcarbonyloxy, halo C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo C 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo C 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy or halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkynyl, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio groupC 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylsulfinyl, halogeno C 1 -C 6 Alkylsulfinyl radical, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylaminosulfonyl, di (C) 1 -C 6 Alkyl) aminosulfonyl, C 1 -C 6 Alkylsulfonylaminocarbonyl group, C 1 -C 6 Alkylcarbonylaminosulfonyl radical, C 3 -C 6 Cycloalkyloxycarbonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halogeno C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkyl carbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylaminocarbonyl, di (C) 1 -C 6 Alkyl) aminocarbonyl, C 2 -C 6 Alkenyloxycarbonyl radical, C 2 -C 6 Alkynyloxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxycarbonyl, arylcarbonyl C which is unsubstituted or substituted by 1 to 5 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C 1 -C 6 Alkyloxycarbonyl, aryl C 1 -C 6 Alkyl, heteroaryl carbonyl C 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C 1 -C 6 Alkyloxycarbonyl, heteroaryl C 1 -C 6 Alkyl, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 4 、R 5 C attached thereto may also form C 3 -C 6 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 6 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted aryl, heteroaryl.
R 8 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, halo-di (C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkylthio, halogeno C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogeno C 2 -C 6 Alkenyloxy radical, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halogeno C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylcarbonyloxy, halo C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo C 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo C 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy or halo C 1 -C 6 Alkoxy radical C 1 -C 6 An alkoxy group.
Further preferably, in the compound of formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer of 0 to 5, and when n is 0, no substituent is provided; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl radicalHalogen substituted C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halo C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 An alkoxycarbonyl group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 C connected thereto may also form C 3 -C 4 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 4 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted phenyl, pyridyl, thienyl, furyl, pyrazolyl, thiazolyl, isothiazolyl, pyrazine, indole, and indole compounds,Pyridazine;
R 8 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halogeno C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 An alkylsulfonyloxy group,C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 An alkoxy group.
Still further preferably, in said compounds of formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 An alkynyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halogeno C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halogeno C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl、C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 An alkoxycarbonyl group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 C connected thereto may also form C 3 -C 4 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 4 A ring of (a);
q is selected from the following substituents:
R 8 selected from halogen, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, aminocarbonyl, di-C 1 -C 4 Alkylaminocarbonyl, dihalo-C 1 -C 4 Alkylaminocarbonyl radical, C 1 -C 4 Alkylthio, halogeno C 1 -C 4 Alkylthio radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 An alkylsulfonyl group.
m is selected from an integer of 0 to 5, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
Still more preferably, in the compounds of formula I:
R 1 selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R 2 selected from the group consisting of fluoro, chloro, bromo, iodo, hydroxy, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer of 0 to 5, and when n is 0, no substituent is provided; when n is greater than 1, R 2 The same or different;
R 3 selected from the group consisting of hydrogen, hydroxy, formyl, acetyl, propionyl, butyryl, trifluoroacetyl, benzoyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoroethoxy, cyclopropyloxy, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, vinyloxycarbonyl, acetylenyloxycarbonyl;
R 4 、R 5 same or different and are respectively selected from hydrogen, fluorine chlorine, bromine, iodine, methyl, ethyl,N-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, or tert-butoxy;
R 6 、R 7 identical or different are each selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
q is selected from the following substituents:
R 8 selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl;
m is selected from an integer of 0 to 5, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
Still more preferably, in the compounds of formula I:
R 1 selected from hydrogen or methyl;
R 3 selected from hydrogen;
R 2 selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, R 2 When in the 4-position of the benzene ring, is not selected from cyano.
R 4 、R 5 The same or different are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R 6 、R 7 are all selected from hydrogen;
n is an integer of 0 to 5, and when n is 0, no substituent is on the ring; when n is greater than 1, R 2 The same or different;
q is selected from the following substituents:
R 8 selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy;
m is an integer of 0 to 4, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl groups: straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl groups: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, and the like. A haloalkyl group: straight-chain or branched alkyl groups in which hydrogen atoms may be partially or wholly replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like. Alkylsulfinyl group: straight or branched chain alkyl groups are attached to the structure via a sulfinyl (-SO-) group, such as methylsulfinyl. A haloalkylsulfinyl group: a straight-chain or branched alkylsulfinyl group in which hydrogen atoms on the alkyl group may be partially or fully substituted with halogen atoms. Haloalkylsulfonyl group: straight-chain or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. Alkylaminosulfenyl: such as CH 3 NHS-、C 2 H 5 NHS-. Dialkylaminosulfenyl: such as (CH) 3 ) 2 NS-、(C 2 H 5 ) 2 NS-. Alkylamino sulfonyl group: alkyl-NH-SO 2 -. Dialkylaminosulfonyl: (alkyl group) 2 -N-SO 2 -. Alkylsulfonylaminocarbonyl group: alkyl-SO 2 -NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO 2 -. Alkylcarbonylalkyl group: alkyl-CO-alkyl-. Alkylsulfonyloxy group: alkyl-S (O) 2 -O-. Haloalkylsulfonyloxy: the hydrogen atoms of the alkyl group of the alkylsulfonyloxy group may be partially or wholly substituted by halogen atoms, e.g. CF 3 -SO 2 -O. Cycloalkyloxycarbonyl group: such as cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, and the like. Alkoxy group: straight or branched chain alkyl groups attached to the structure via oxygen atom linkages. Haloalkoxy groups: straight-chain or branched alkoxy groups, in which the hydrogen atoms may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like. Halogenated alkoxycarbonyl group: the hydrogen atoms of the alkyl group of the alkoxycarbonyl group may be partially or wholly replaced by halogen atoms, e.g. ClCH 2 CH 2 OCO-、CF 3 CH 2 OCO-, etc. An alkoxyalkyl group: alkyl-O-alkyl-, e.g. CH 3 OCH 2 -. Haloalkoxyalkyl groups: the hydrogen atoms of the alkyl group of the alkoxyalkyl group may be partially or fully substituted by halogen atoms, e.g., clCH 2 CH 2 OCH 2 -、CF 3 CH 2 OCH 2 -and the like. An alkoxycarbonylalkyl group: alkoxycarbonyl-alkyl-, e.g. CH 3 OCOCH 2 -. Haloalkoxycarbonylalkyl: the hydrogen atoms of the alkyl group of the alkoxycarbonylalkyl group may be partially or fully substituted by halogen atoms, e.g. CF 3 CH 2 OCOCH 2 -. Alkylcarbonyloxy group: such as CH 3 COO-, etc. Haloalkylcarbonyloxy: the hydrogen atoms of the alkylcarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF 3 COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, e.g. CH 3 OCOO-. Halogenated alkoxycarbonyloxy group: the hydrogen atoms of the alkyl group of the alkoxycarbonyloxy group may be partially or fully substituted by halogen atoms, e.g. CF 3 OCOO-. Alkylthio-carbonylalkyl: alkylthiocarbonyl-alkyl-, e.g. CH 3 SCOCH 2 -. Halogenoalkylthio carbonylAlkyl radical: the hydrogen atoms of the alkyl group of the alkylthiocarbonylalkyl group may be partially or wholly substituted by halogen atoms, e.g. CF 3 CH 2 SCOCH 2 -. Alkoxy groups: such as CH 3 OCH 2 O-, etc. Haloalkoxyalkyl: the hydrogen atoms of the alkoxy groups being partially or wholly replaced by halogen atoms, e.g. CF 3 OCH 2 O-is added. Alkoxy alkoxycarbonyl group: such as CH 3 OCH 2 CH 2 OCO-, etc. Alkylthio groups: straight or branched chain alkyl groups attached to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkylthioalkyl: alkyl-S-alkyl-, e.g. CH 3 SCH 2 -. Haloalkylthioalkyl: the hydrogen atoms of the alkyl group of an alkylthioalkyl group may be partially or fully substituted by halogen atoms, e.g. ClCH 2 CH 2 SCH 2 -、CF 3 CH 2 SCH 2 -and the like. Alkylamino group: straight or branched chain alkyl groups attached to the structure via a nitrogen atom. Haloalkylamino group: straight-chain or branched alkylamino groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. Dialkylamino group: such as (CH) 3 ) 2 N-，(CH 3 CH 2 ) 2 N-is provided. Halogenated dialkylamino group: the hydrogen atoms of the alkyl groups being partially or wholly replaced by halogen atoms, e.g. (CF) 3 ) 2 N-，(CF 3 CH 2 ) 2 N-is provided. Alkenyl: straight-chain or branched alkenes, for example ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1, 2-allenyl and 2, 4-hexadienyl. Halogenated alkenyl groups: straight-chain or branched alkenes in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenyloxy: linear or branched alkenes linked to the structure via oxygen atoms. Haloalkenyloxy: straight-chain or branched alkenyloxy groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkenylthio group: straight-chain or branched alkenes, viaThe sulfur atom is bonded to the structure. Such as CH 2 ＝CHCH 2 S-. Alkenyloxycarbonyl radical: such as CH 2 ＝CHCH 2 OCO-, etc. Alkynyl: straight-chain or branched alkynes, for example ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups consisting of multiple triple bonds, such as 2, 5-hexadiynyl. Halogenated alkynyl group: straight-chain or branched alkynes, in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkynyloxy: straight or branched alkynes, attached to the structure via oxygen atom bonds. Haloalkynyloxy: straight-chain or branched alkynyloxy, in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkynyloxycarbonyl group: such as CH ≡ CCH 2 OCO-, etc. An alkylsulfonyl group: straight or branched chain alkyl via sulfonyl (-SO) 2 -) is attached to a structure, such as a methylsulfonyl group. Haloalkylsulfonyl group: straight-chain or branched alkylsulfonyl wherein the hydrogen atoms of the alkyl group may be partially or wholly substituted by halogen atoms. An alkylcarbonyl group: the alkyl radical being bound to the structure via a carbonyl group, e.g. CH 3 CO-，CH 3 CH 2 CO-. A halogenated alkylcarbonyl group: the hydrogen atoms of the alkyl group of the alkylcarbonyl group may be partially or fully substituted with halogen atoms, e.g. CF 3 CO-. Alkoxycarbonyl group: the alkoxy group is attached to the structure via a carbonyl group. Such as CH 3 OCO-，CH 3 CH 2 OCO-. An aminocarbonyl group: such as NH 2 CO-. Alkyl amino carbonyl: alkyl-NH-CO-, e.g. CH 3 NHCO-，CH 3 CH 2 NHCO-. Dialkylaminocarbonyl group: such as (CH) 3 ) 2 NCO-，(CH 3 CH 2 ) 2 NCO-. The aryl moiety in (hetero) aryl, (hetero) arylalkyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl, (hetero) arylcarbonylalkyl, (hetero) aryloxycarbonyl, (hetero) arylalkyloxycarbonyl, and the like includes phenyl or naphthyl. Heteroaryl is a five or six membered ring containing 1 or more heteroatoms N, O, S. Such as furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl and the like. (hetero) aryl group: such as phenyl, and the like. (hetero) arylalkyl: such as benzyl, phenethyl, p-chlorobenzyl, 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl and the like. (hetero) arylcarbonyl group: such as benzoyl, 4-chlorobenzoyl and the like. (hetero) arylmethylcarbonyl: such as PhCH 2 CO-. (hetero) arylcarbonylalkyl: such as PhCOCH 2 -. (hetero) aryloxycarbonyl group: such as phenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-nitrophenoxycarbonyl, naphthyloxycarbonyl, etc. Arylalkyloxycarbonyl group: such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethylbenzyloxycarbonyl and the like. (hetero) arylalkyloxycarbonyl: such as PhCH 2 OCO-、4-Cl-PhCH 2 OCO-, etc.
Table 1, table 2, table 3, table 4 and Table 5 show the values of R in the general formula I 1 、R 3 、R 4 And R 5 、R 6 And R 7 And Q are not limited to these substituents.
TABLE 1R 1 Substituent group
| R 8 | R 8 | R 8 | R 8 |
| H | CN | CH 3 | C 2 H 5 |
| n-C 3 H 7 | i-C 3 H 7 | n-C 4 H 9 | s-C 4 H 9 |
| i-C 4 H 9 | t-C 4 H 9 | CF 3 | CCl 3 |
| CHF 2 | CH 2 F | CH 2 Cl | CH 2 CF 3 |
| CF 2 CF 3 | COOCH 3 | Ph | Ph-4-Cl |
TABLE 2R 3 Substituent group
TABLE 3R 4 (R 5 ) Substituent group
TABLE 4R 6 (R 7 ) Substituent group
TABLE 5Q substituents
Some of the compounds of the present invention can be illustrated by specific compounds listed in tables 6 to 34, but are not intended to limit the present invention. In the compounds of the general formula I referred to in the table, R 1 ＝R 3 ＝R 4 ＝R 5 ＝R 6 ＝R 7 ＝H。
In formula I, when the five-membered ring is a double bond, the formula structure is as follows:
in the general formula I-1, (R) when Q = Q1 2 ) n The substituents are shown in Table 6, and represent the compound numbers of 6-1-6-288 in sequence.
TABLE 6
Table 7: in the general formula I-1, when Q = Q2, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compounds having the numbers in turn from 7-1-7-288.
Table 8: in the general formula I-1, when Q = Q3, a substituent (R) 2 ) n In accordance with the substituents indicated in Table 6, the substituents correspond in turn to 6-1-6-288 in Table 6, representing compound numbers of 8-1-8-288 in turn.
Table 9: in the general formula I-1, when Q = Q4, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers of 9-1-9-288 in turn.
Table 10: in the general formula I-1, when Q = Q5, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers of 10-1-10-288 in turn.
Table 11: in the general formula I-1, when Q = Q6, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers 11-1-11-288.
Table 12: in the general formula I-1, when Q = Q7, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers of 12-1-12-288 in turn.
Table 13: in the general formula I-1, when Q = Q8, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers 13-1-13-288.
Table 14: in the general formula I-1, when Q = Q9, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers in turn 14-1-14-288.
In the formula I, when the five-membered ring is a single bond, the formula structure is as follows:
table 15: in the general formula I-2, when Q = Q1, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compounds numbered in turn from 15-1-15-288.
Table 16: in the general formula I-2, when Q = Q2, the substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers in turn 16-1-16-288.
Table 17: in the general formula I-2, when Q = Q3, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers of 17-1-17-288 in turn.
Table 18: in the general formula I-2, when Q = Q4, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers in turn 18-1-18-288.
Table 19: in the general formula I-2, when Q = Q5, a substituent (R) 2 ) n In accordance with the substituents given in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, representing compound numbers of 19-1-19-288 in turn.
Table 20: in the general formula I-2, when Q = Q6, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers in turn from 20-1-20-288.
Table 21: in the general formula I-2, when Q = Q7, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compounds numbered in turn from 21-1-21-288.
Table 22: in the general formula I-2, when Q = Q8, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to 6-1-6-288 of Table 6, and represent the compound numbers in turn 22-1-22-288.
Table 23: in the general formula I-2, when Q = Q9, a substituent (R) 2 ) n In accordance with the substituents shown in Table 6, the substituents correspond in turn to Table 66-1-6-288 represents the compound number of 23-1-23-288 in sequence.
In the general formula I-1, when Q = Q1, the substituent R 3 (in the absence of hydrogen) are different substituents as shown in Table 24, representing compounds numbered 24-1-24-140 in sequence.
TABLE 24
The compounds of the invention are prepared according to the following process, the reaction scheme being as follows, wherein the groups are as defined above unless otherwise stated:
the compounds of formula I are prepared by the following method:
the intermediates II and III are reacted under basic conditions in a suitable solvent to give the compounds of the general formula I.
Suitable bases may be selected from, for example, triethylamine, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium or sodium tert-butoxide, etc.
The reaction is carried out in a suitable solvent which may be selected from, for example, dichloromethane, tetrahydrofuran, 1, 4-dioxane, acetonitrile, toluene, xylene, benzene, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetone, or butanone.
The reaction temperature may be between room temperature and the boiling temperature of the solvent, and is generally from 20 to 100 ℃.
The reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
Intermediate III is commercially available and can be prepared by known methods, such as CN108947892, journal of Medicinal Chemistry 46 (23), 4895-4903;2003, etc.
Intermediate II is a key intermediate for preparing the compound of the general formula I, and is prepared by the following method:
4-Bromobutylkyne is reacted with potassium phthalimide in a suitable solvent at a suitable temperature for 30 minutes to 20 hours, typically 1 to 10 hours, to give intermediate M1, a procedure which is described in WO2002028395 and Organic Letters,7 (4), 733-736;2005; chlorination of 4-chlorobenzaldehyde oxime followed by reaction with M1 in a suitable solvent under basic conditions gives M2, a procedure which is described in WO2006065280 and Chemical Communications (Cambridge, united Kingdom), 47 (11), 3198-3200;2011; deamination of M2 in a suitable solvent under basic conditions to give II, this procedure being described in European Journal of Organic Chemistry,2013 (23), 5143-5148;2013 and WO2016011209 and the like.
Although the compounds of the general formula I of the invention also belong to the substituted isoxazole ethylamine class compounds with certain compounds disclosed in the prior art, the structural characteristics still have significant differences. And the compound of the present invention has better bactericidal activity due to the difference in these structures.
The compound of the general formula I shows excellent activity on various pathogenic bacteria in the agricultural or other fields, so the technical scheme of the invention also comprises the application of the compound of the general formula I in the agricultural or other fields for preparing bactericides.
The examples of diseases mentioned below are intended to illustrate the invention, but in no way limit it.
The compounds of the general formula I can be used for controlling the following diseases: oomycete diseases such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, luffa downy mildew, wax gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, cabbage white rust), damping-off (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (pepper blight, luffa blight, wax gourd blight), blight (broad bean blight, cucumber blight, pumpkin blight, wax gourd blight, watermelon blight, melon blight, hot pepper, leek blight, garlic blight, cotton blight, late blight (potato blight, tomato late blight), and the like; <xnotran> , ( , , , , , , , , , , , , , , , ), ( , , , , , , ), ( , , , , ), ( , , , , , , , , , , , , , , , , ), ( , , , , ), ( , , ), ( , , , , , , , ), ( , , , , , , , , , ), ( , </xnotran> Black spot of rape, black spot of sesame, black spot of sunflower, black spot of castor, black spot of tomato, black spot of pepper, black spot of eggplant, black spot of bean, black spot of cucumber, black spot of celery, black rot of carrot, black spot of apple, black spot of peanut), spot blight (tomato spot blight, pepper spot blight, celery spot blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (tomato stem base rot, bean stem base rot), and others (corn northern leaf blight, kenaf waist break disease, rice blast, black sheath blight, sugarcane eye spot disease, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot disease, melon northern leaf spot disease, peanut net spot disease, tea red leaf spot disease, pepper white spot disease, wax gourd leaf spot disease, celery black rot disease, spinach heart rot, kenaf leaf mold, kenaf spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, brown speck disease, kidney bean red spot disease, bitter gourd white spot disease, watermelon spot disease, jute rot disease, sunflower root rot disease, kidney bean carbon rot disease, soybean target spot disease, eggplant rod spore leaf spot disease, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot disease, etc.); basidiomycete diseases such as rust (wheat stripe rust, wheat stalk rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum stalk smut, chestnut kernel smut, sugarcane head smut, kidney bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); ascomycetous diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, towel gourd powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclerotinia rot, rape sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, kidney bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, bitter gourd sclerotinia rot, wax gourd sclerotinia rot, watermelon sclerotinia rot, celery sclerotinia rot), scab (apple scab, pear scab) and the like.
Owing to their positive properties, the abovementioned compounds can be used advantageously for protecting crops, domestic animals and breeding animals of agricultural and horticultural importance, as well as the environment in which humans are often exposed, against harmful germs, pests and mites.
The amount of the compound used to achieve the desired effect will vary depending upon factors such as the compound used, the crop to be protected, the type of pest, the extent of infestation, climatic conditions, the method of application, the dosage form employed.
A dose of 10g to 5 kg of compound per hectare provides adequate control.
The technical scheme of the invention also comprises a method for preventing and controlling germs and pests and mites, which comprises the following steps: the bactericidal, insecticidal and acaricidal compound of the invention is applied to the germs or the growth medium thereof. Preferably, an effective amount of 10 to 1000 grams per hectare is generally selected, with an effective amount of 20 to 500 grams per hectare being preferred.
For certain applications, for example in agriculture, one or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers and the like can be added to the fungicidal, insecticidal and acaricidal compositions of the present invention, whereby additional advantages and effects can be produced.
Detailed Description
The following specific examples are intended to further illustrate the invention, but the invention is in no way limited to these examples (all materials are commercially available unless otherwise indicated).
Synthetic examples
Example 1: preparation of intermediate 2- (3- (4-p-chlorophenyl) isoxazol-5-yl) -1-ethylamine
1) Preparation of N- (3-butyne) phthalimide
13.30g (0.10 mol) of 4-bromobutyyne and 18.5g (0.1 mol) of phthalimide potassium salt were put into 100ml of a solvent of N, N-dimethylformamide with stirring at room temperature, reacted for 5 to 7 hours with stirring at 60 ℃, then 50 to 100ml of water was added to the reaction solution, and washed with suction filtration water to obtain 18.3g of a white solid with a yield of 92%.
2) Preparation of 2- (3- (4-p-chlorophenyl) isoxazol-5-yl) -1-ethylamine
15.5g (0.1 mol) of 4-chlorobenzaldehyde oxime was dissolved in 50ml of N, N-dimethylformamide, 14.7g (0.11 mol) of NCS was added to a reaction flask in portions with stirring and allowed to react at 50 ℃ for 3 to 4 hours, after the completion of the reaction of 4-chlorobenzaldehyde oxime was monitored by TLC, 19.9g (0.1 mol) of N- (3-butyne) phthalimide and 8.4g (0.1 mol) of sodium hydrogencarbonate were added and allowed to react for 4 hours, after the completion of the reaction monitored by TLC, the reaction solution was cooled and poured into water and stirred for 30 minutes, filtered and washed with water to obtain 13.2g of a white solid with a yield of 37.4%.
Dissolving the white solid obtained in the step into 300ml of THF and 60ml of DCM, adding 9.4g of hydrazine hydrate, reacting for 3-4 hours at 50 ℃, monitoring the complete reaction of N- (2- (3- (4-chlorophenyl) isoxazol-5-yl) ethyl) phthalimide by TLC, cooling, filtering, concentrating the filtrate under reduced pressure, adding DCM for dissolving, washing the organic phase with a sodium hydroxide solution, and drying over anhydrous magnesium sulfate to obtain 7.3g of light yellow solid 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine with the yield of 87.6%.
Example 2: preparation of intermediates
1) Preparation of N- (3-butene) phthalimide
13.50g (0.10 mol) of 4-bromobutyyne and 18.5g (0.1 mol) of phthalimide potassium salt were put into 100ml of a solvent of N, N-dimethylformamide with stirring at room temperature, reacted for 5 to 7 hours with stirring at 60 ℃, then 50 to 100ml of water was added to the reaction solution, and washed with suction filtration water to obtain 17.6g of a white solid with a yield of 87.6%.
2) Preparation of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine
15.5g (0.1 mol) of 4-chlorobenzaldehyde oxime is dissolved in 50ml of N, N-dimethylformamide solution, 14.7g (0.11 mol) of NCS is added into a reaction bottle in batches under stirring, the reaction lasts for 3 to 4 hours at 50 ℃, 20.1g (0.1 mol) of N- (3-butyne) phthalimide and 8.4g (0.1 mol) of sodium bicarbonate are added after the TLC monitors that the 4-chlorobenzaldehyde oxime is completely reacted, the reaction is continued for 4 hours, after the TLC monitors that the reaction is finished, the reaction liquid is cooled and poured into water to be stirred for 30 minutes, and after the reaction is monitored by the TLC, 14.3g of white solid is obtained by filtration and washing by water, and the yield is 40.3 percent.
Dissolving the white solid obtained in the step into 300ml of THF and 60ml of DCM, adding 10g of hydrazine hydrate, reacting for 3-4 hours at 50 ℃, monitoring the complete reaction of N- (2- (3- (4-chlorophenyl) isoxazol-5-yl) ethyl) phthalimide by TLC, cooling, filtering, concentrating the filtrate under reduced pressure, adding DCM for dissolving, washing the organic phase with sodium hydroxide solution, and drying over anhydrous magnesium sulfate to obtain 6.9g of light yellow solid 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine with the yield of 76.2%.
Example 3: preparation of Compounds 6-19
0.22g (10 mmol) of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine was dissolved in 20ml of acetonitrile solvent, 0.23g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5ml of acetonitrile was added dropwise with stirring to the reaction flask, the reaction was carried out at room temperature for 3 to 4 hours, after completion of the reaction by TLC, the solvent was distilled off under reduced pressure, ethyl acetate (3X 50 ml) was added for extraction, the organic phase was washed with 50ml of saturated saline solution, and after the removal of the solvent, column chromatography was carried out on the residue to obtain 0.24g of a yellow oily substance with a yield of 60.8%.
1 H-NMR (600 MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):7.69(m,3H),7.54(m,2H),7.50(m,1H),7.42(m,2H),6.41(s,1H),6.15(s,1H),3.85(m,2H),3.17(m,2H).
Example 4: preparation of Compounds 16-19
0.22g (10 mmol) of 2- (3- (4-chlorophenyl) isoxazol-5-yl) -1-ethylamine was dissolved in 20ml of acetonitrile solvent, 0.24g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5ml of acetonitrile was added dropwise to a reaction flask with stirring, the reaction was carried out at room temperature for 3 to 4 hours, after the completion of the reaction was monitored by TLC, the solvent was distilled off under reduced pressure, ethyl acetate (3X 50 ml) was added for extraction, the organic phase was washed with 50ml of saturated saline, and after the removal, column chromatography was carried out on the residue to obtain 0.20g of a white solid with a yield of 49.4%.
1 H-NMR (600 MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):δ(CDCl 3 ):7.61(m,2H),7.50(s,1H),7.40(m,2H),4.92(m,1H),3.82(m,1H),3.62(m,1H),3.55(m,1H),3.05(m,1H),2.05(m,2H).
Other compounds of the invention may be prepared by reference to the above examples.
Physical property data and nuclear magnetic data of some of the compounds ( 1 HNMR,600MHz, internal standard TMS, ppm) as follows:
compound 6-1. Delta (CDCl) 3 ):7.74(m,2H),7.68(m,1H),7.54(m,3H),7.43(m,3H),6.42(s,1H),6.24(s,1H),3.85(m,2H),3.17(m,2H).
Compound 6-4. Delta (CDCl) 3 ):7.79(m,2H),7.68(m,1H),7.57(m,2H),7.52(m,1H),7.28(m,2H),6.42(s,1H),6.16(s,1H),3.85(m,2H),3.18(m,2H).
6-17 melting point 96.0 deg.C for compound. Delta (CDCl) 3 ):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.48(m,1H),7.39(m,1H),7.34(m,1H),6.59(s,1H),6.09(s,1H),3.87(m,2H),3.21(m,2H).
Compounds 6-21. Delta (CDCl) 3 ):7.70(m,1H),7.66(m,1H),7.59(m,2H),7.54(m,2H),7.34(m,1H),6.59(s,1H),6.08(s,1H),3.87(m,2H),3.21(m,2H).
Compounds 6-49. Delta (CDCl) 3 ):7.90(m,2H),7.75(m,2H),7.70(m,1H),7.55(m,2H),7.25(m,1H),6.50(s,1H),6.07(s,1H),3.88(m,2H),3.21(m,2H).
Compounds 6-57. Delta (CDCl) 3 ):7.67(m,1H),7.62(m,2H),7.47(m,2H),7.45(m,1H),7.22(m,2H),6.38(s,1H),6.28(s,1H),3.83(m,2H),3.13(m,2H),2.38(s,3H).
The melting point of the compound is 6-55 ℃ and 90.8 ℃. Delta (CDCl) 3 ):7.69(m,1H),7.57(m,1H),7.52(m,2H),7.45(m,1H),7.33(m,1H),7.26(m,2H),6.30(s,1H),6.16(s,1H),3.86(m,2H),3.18(m,2H),2.45(s,3H).
Compounds 6-60. Delta (CDCl) 3 ):7.70(m,1H),7.58(m,1H),7.53(m,2H),7.29(s,1H),7.16(m,2H),6.29(s,1H),6.15(s,1H),3.86(m,2H),3.18(m,2H),2.40(s,3H),2.34(s,3H).
Compounds 6-69 melting point 153.9 ℃. Delta (CDCl) 3 ):7.90(m,2H),7.70(m,3H),7.59(m,1H),7.52(m,2H),6.49(s,1H),6.08(s,1H),3.88(m,2H),3.21(m,2H).
Compound 6-78. Delta (CDCl) 3 ):7.72(m,2H),7.68(m,1H),7.54(m,2H),7.48(m,1H),7.12(m,2H),6.39(s,1H),6.22(s,1H),3.84(m,2H),3.16(m,2H).
6-151 deg.C, mp 117.0 deg.C. Delta (CDCl) 3 ):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.24(m,1H),7.08(m,1H),6.57(s,1H),6.07(s,1H),3.87(m,2H),3.20(m,2H).
Compound 7-4, melting point 161.8 ℃. Delta (CDCl) 3 ):7.77(m,2H),7.15(m,2H),7.12(s,1H),6.40(s,1H),3.90(m,2H),3.20(m,2H).
Compounds 7-19: delta (CDCl) 3 ):7.72(m,2H),7.44(m,2H),7.12(s,1H),6.41(s,1H),3.90(m,2H),3.21(m,2H).
Compounds 9-19. Delta (CDCl) 3 ):8.61(m,1H),8.22(m,1H),7.71(m,3H),7.43(m,2H),6.48(s,1H),6.20(s,1H),3.90(m,2H),3.24(m,2H),3.11(s,3H).
Compound 10-19: delta (CDCl) 3 ):7.91(s,1H),7.71(m,2H),7.43(m,2H),6.81(t,1H),6.59(s,1H),6.39(s,1H),3.91(s,3H),3.80(m,2H),3.14(m,2H).
Compounds 10-21. Delta (CDCl) 3 ):7.90(s,1H),7.58(m,1H),7.47(m,1H),7.31(m,1H),6.80(t,1H),6.58(s,1H),6.41(s,1H),3.90(s,3H),3.81(m,2H),3.15(m,2H).
Compound 11-4, melting point 103.9. Delta (CDCl) 3 ):7.74(m,2H),7.29(m,2H),7.24(m,1H),7.13(m,2H),6.43(s,1H),6.15(s,1H),3.90(m,2H),3.21(m,2H).
Compounds 11-19: delta (CDCl) 3 ):7.70(m,2H),7.43(m,2H),7.25(m,3H),6.45(s,1H),6.10(s,1H),3.90(m,2H),3.22(m,2H).
Compound 12-4 melting point 126 ℃. Delta (CDCl) 3 ):8.45(m,1H),8.08(m,1H),7.76(m,2H),7.34(m,1H),7.15(m,2H),6.76(s,1H),6.41(s,1H),3.90(m,2H),3.21(m,2H).
Compounds 12-19: delta (CDCl) 3 ):8.451(d,1H),7.72(m,2H),7.65(s,1H),7.51(m,1H),7.43(m,1H),6.55(s,1H),6.40(s,1H),3.87(m,2H),3.19(m,2H).
Compounds 13-19. Delta (CDCl) 3 ):7.71(m,2H),7.34(m,2H),6.28(s,1H),6.29(s,1H),6.24(s,1H),4.10(s,3H),3.78(m,2H),3.15(m,2H),2.23(s,3H).
Compounds 14-19: delta (CDCl) 3 ):7.70(m,2H),7.42(m,2H),6.40(s,1H),6.39(s,1H),3.83(m,2H),3.16(m,2H),2.72(s,3H).
Compound 15-4. Delta (CDCl) 3 ):7.68(m,1H),7.63(m,2H),7.58(m,1H),7.53(m,2H),7.45(s,1H),7.09(m,1H),6.37(s,1H),4.87(m,1H),3.70(m,1H),3.61(m,1H),3.48(m,1H),3.06(m,1H),2.09(m,1H),1.98(m,1H).
Compounds 15-17. Delta (CDCl) 3 ):7.69(m,1H),7.59(m,2H),7.53(m,2H),7.43(m,1H),7.35(m,1H),7.30(m,1H),6.33(s,1H),4.90(m,1H),3.73(m,1H),3.63(m,2H),3.25(m,1H),2.10(m,1H),2.04(m,1H).
Compounds 15-19: delta (CDCl) 3 ):7.70(m,1H),7.63(m,2H),7.58(m,3H),7.38(m,2H),6.31(s,1H),4.88(m,1H),3.70(m,2H),3.50(m,1H),3.05(m,1H),2.05(m,2H),.
15-21 parts of compound, the melting point is 102.2 ℃. Delta (CDCl) 3 ):7.69(m,1H),7.55(m,4H),7.45(s,1H),7.28(m,1H),6.30(s,1H),4.90(m,1H),3.71(m,1H),3.62(m,2H),3.22(m,1H),2.05(m,2H).
Compounds 15-60. Delta (CDCl) 3 ):7.70(m,1H),7.58(m,1H),7.52(m,2H),7.15(m,2H),7.11(m,1H),6.33(s,1H),4.81(m,1H),3.74(m,1H),3.60(m,1H),3.55(m,1H),3.13(m,1H),2.48(s,3H),2.34(s,3H),2.09(m,1H),1.99(m,1H).
15-69 parts of compound, melting point 139 ℃. Delta (CDCl) 3 ):7.77(m,2H),7.70(m,1H),7.66(m,2H),7.60(m,1H),7.54(m,2H),6.26(s,1H),4.94(m,1H),3.71(m,1H),3.64(m,1H),3.53(m,1H),3.10(m,1H),2.13(m,1H),2.02(m,1H).
Compounds 15 to 78. Delta (CDCl) 3 ):7.68(m,3H),7.58(m,1H),7.53(m,2H),7.25(m,2H),6.37(s,1H),4.89(m,1H),3.68(m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.99(m,1H).
15-151 parts of compound, melting point 60.5 ℃. Delta (CDCl) 3 ):7.69(m,1H),7.60(m,2H),7.53(m,2H),7.18(m,1H),7.03(m,1H),6.31(s,1H),4.90(m,1H),3.73(m,1H),3.61(m,2H),3.22(m,1H),2.10(m,1H),2.01(m,1H).
Compound 15-288. Delta (CDCl) 3 ):7.69(m,1H),7.58(m,3H),7.52(m,2H),7.42(m,2H),6.35(s,1H),4.85(m,1H),3.73(m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.97(m,1H),1.33(s,3H).
Compound 16-4. Delta (CDCl) 3 ):7.65(m,2H),7.51(s,1H),7.11(m,2H),4.90(m,1H),3.83(m,1H),3.62(m,1H),3.52(m,1H),3.06(m,1H),2.12(m,1H),2.02(m,1H).
Compounds 16-17. Delta (CDCl) 3 ):7.60(m,1H),7.52(s,1H),7.43(m,1H),7.37(m,1H),7.31(m,1H),4.93(m,1H),3.85(m,1H),3.65(m,2H),3.26(m,1H),2.07(m,2H).
16-21 parts of compound, melting point 112.8 ℃. Delta (CDCl) 3 ):7.59(m,1H),7.48(s,1H),7.45(m,1H),7.30(m,1H),4.93(m,1H),3.84(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).
Compounds 16-60. Delta (CDCl) 3 ):7.58(s,1H),7.16(m,1H),7.12(m,2H),4.85(m,1H),3.85(m,1H),3.63(m,1H),3.57(m,1H),3.12(m,1H),2.49(s,3H),2.34(s,3H),2.09(m,1H),2.01(m,1H).
16-69 melting point 104.8 ℃. Delta (CDCl) 3 ):7.78(m,3H),7.67(m,2H),7.47(s,1H),4.96(m,1H),3.83(m,1H),3.62(m,1H),3.54(m,1H),3.09(m,1H),2.14(m,1H),2.04(m,1H).
Compounds 16 to 78. Delta (CDCl) 3 ):7.70(m,2H),7.50(s,1H),7.25(m,2H),4.93(m,1H),3.83(m,1H),3.63(m,1H),3.52(m,1H),3.07(m,1H),2.13(m,1H),2.02(m,1H).
Compound 16-151 with melting point 106.1 ℃. Delta (CDCl) 3 ):7.63(m,1H),7.50(s,1H),7.19(m,1H),7.05(m,1H),4.92(m,1H),3.85(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).
16-288 melting Point 142 ℃. Delta (CDCl) 3 ):7.60(m,2H),7.54(s,1H),7.43(m,2H),4.89(m,1H),3.84(m,1H),3.63(m,1H),3.52(m,1H),3.07(m,1H),2.11(m,1H),2.00(m,1H),1.33(s,3H).
Compounds 17-19, mp 184.1 ℃. Delta (CDCl) 3 ):8.00(d,1H),7.88(m,1H),7.80(m,1H),7.59(m,2H),7.40(m,2H),6.69(s,1H),4.92(m,1H),3.80(m,1H),3.64(m,1H),3.51(m,1H),3.08(m,4H),2.13(m,1H),2.03(m,1H).
18-19 melting point 189.1 ℃. Delta (CDCl) 3 ):8.60(d,1H),8.22(m,1H),7.78(m,1H),7.57(m,2H),7.39(m,2H),6.65(s,1H),4.92(m,1H),3.79(m,1H),3.63(m,1H),3.52(m,1H),3.12(s,3H),3.08(m,1H),2.14(m,1H),2.02(m,1H).
Compounds 19-19: delta (CDCl) 3 ):7.88(s,1H),7.59(m,2H),7.37(m,2H),6.90(t,1H),6.64(s,1H),4.87(m,1H),3.93(s,3H),3.61(m,2H),3.46(m,1H),3.03(m,1H),2.03(m,2H).
Compounds 20-19 Beta (CDCl) 3 ):7.57(m,2H),7.37(m,2H),7.25(m,3H),6.27(s,1H),4.93(m,1H),3.68(m,2H),3.48(m,1H),2.07(m,2H).
Compounds 21-19: delta (CDCl) 3 ):8.52(d,1H),7.71(m,1H),7.60(m,2H),7.54(m,1H),7.39(m,2H),6.97(s,1H),4.92(m,1H),3.82(m,1H),3.56(m,2H),3.07(m,1H),2.05(m,2H).
Compounds 22 to 19. Delta (CDCl) 3 ):7.70(m,2H),7.35(m,2H),6.29(s,1H),6.27(s,1H),6.24(s,1H),4.11(s,3H),3.79(m,2H),3.16(m,2H),2.23(s,3H).
Compounds 23-19: delta (CDCl) 3 ):7.58(m,2H),7.38(m,2H),6.64(s,1H),4.86(m,1H),3.62(m,2H),3.48(m,1H),3.05(m,1H),2.74(s,3H),2.01(m,2H).
Meanwhile, other compounds represented by the general formula I of the present invention can be obtained by substituting the corresponding raw materials according to the contents described in the above synthetic examples.
Examples of measurement of biological Activity
The compound of the invention has good activity to various germs in the agricultural field.
Example 5: measurement of fungicidal Activity
The compound sample of the invention is used for carrying out in vitro bacteriostatic activity or in vivo protection effect test on a plurality of fungal diseases of plants. The results of the bactericidal activity measurement are shown in the following examples.
(1) In vitro bactericidal activity assay
The measurement method is as follows: the high-throughput screening method is adopted, i.e. a compound sample to be detected is dissolved by using a proper solvent (the type of the solvent is acetone, methanol, DMF, and the like, and is selected according to the dissolving capacity of the solvent on the sample), and a liquid to be detected with the required concentration is prepared. Under an ultraclean working environment, adding a solution to be detected into micropores of a 96-hole culture plate, adding a pathogen propagule suspension into the micropore, and placing the treated culture plate in a constant-temperature incubator for culture. And (4) after 24 hours, carrying out investigation, visually observing the germination or growth condition of the pathogen propagules during the investigation, and evaluating the bacteriostatic activity of the compound according to the germination or growth condition of the control treatment.
The results of the in vitro bacteriostatic activity (expressed as inhibition) test of some compounds are as follows:
inhibition rate against rice blast germs:
at a dosage of 25ppm, the compound provided by the invention has good inhibition rate on rice blast, for example, the inhibition rate of the compound 12-19 and the like on the rice blast is more than 80%.
(2) Living body protecting Activity assay
The measurement method is as follows: the living potted plant assay method is adopted, i.e., a sample of a compound to be tested is dissolved in a small amount of solvent (the type of solvent is acetone, methanol, DMF, etc., and is selected according to the dissolving capacity of the solvent for the sample, and the volume ratio of the amount of the solvent to the amount of sprayed liquid is equal to or less than 0.05), and diluted with water containing 0.1% Tween 80 to prepare a solution to be tested with a required concentration. The solution to be tested is sprayed on diseased host plants (the host plants are standard potted seedlings cultured in a greenhouse) on a crop sprayer, and disease inoculation is carried out after 24 hours. According to the characteristics of diseases, inoculating the disease plants needing temperature and moisture control culture, then culturing in an artificial climate chamber, transferring into a greenhouse for culture after the diseases are infected, and directly inoculating and culturing the disease plants without moisture control culture in the greenhouse. The compound disease control effect evaluation is performed after the control is sufficiently ill (usually a week).
The results of the in vivo protective activity test of some compounds are as follows:
(1) Downy mildew of cucumber
Under the dosage of 400ppm, the compound provided by the invention has good inhibition rate on cucumber downy mildew, for example, the compound has the effects of 6-1, 6-4, 6-19, 6-57, 6-78, 6-288, 7-4, 10-21, 11-4, 12-19, 13-19, 14-19, 15-21, 15-151, 15-69, 16-4, 16-17, 16-19, 16-21, 16-60, 16-69, 16-78, 16-151, 16-288, 19-19, 20-19, 21-19, 23-19 and the like, and the control effect on cucumber downy mildew is more than 80%;
under the dosage of 100ppm, the compounds 6-19, 6-288, 12-19, 13-19, 16-69 and 16-151 have good inhibition rate on cucumber downy mildew, and the control effect on cucumber downy mildew is more than 85%;
under the dosage of 25ppm, the compounds 6-19 and 12-19 have better inhibition rate on cucumber downy mildew, for example, the control effect on cucumber downy mildew is more than 90%;
(2) Powdery mildew of wheat
Under the dosage of 400ppm, the compound provided by the invention has good inhibition rate on wheat powdery mildew, for example, the compound has the control effect on wheat powdery mildew of more than 80 percent, such as 6-57, 6-288, 11-4, 12-19, 16-4, 16-60, 23-19 and the like;
under the dosage of 100ppm, the compounds 6-57, 6-288 and 16-60 have good inhibition rate on wheat powdery mildew, and the control effect on the wheat powdery mildew is more than 85 percent;
under the dosage of 25ppm, the compounds 6-57 and 6-288 have better inhibition rate on wheat powdery mildew, and the control effect on the wheat powdery mildew is more than 90 percent;
(3) Rust disease of maize
Under the dosage of 400ppm, the compound provided by the invention has good inhibition rate on corn rust, for example, the compound has the effects of 6-1, 7-4, 10-21, 11-4, 12-19 and the like, and the control effect on the corn rust is more than 80%;
under the dosage of 100ppm, the compounds 7-4, 10-21, 11-4 and 12-4 have good inhibition rate on corn rust and have the corn rust prevention effect of more than 85 percent;
(4) Anthracnose of cucumber
Under the dosage of 400ppm, the compound provided by the invention has good inhibition rate on melon anthracnose, for example, compounds 6-151, 16-17, 16-19, 16-21, 16-60, 16-151, 18-19 and the like have the control effect on melon anthracnose of more than 80%.
Under the dosage of 100ppm, the compounds 16-17, 16-19, 16-21, 16-69 and 16-151 have good inhibition rate on melon anthracnose, and the control effect on corn rust is over 85 percent;
under the dosage of 25ppm, the compounds 16-19, 16-21 and 16-151 have good inhibition rate on melon anthracnose, and the control effect on wheat powdery mildew is more than 90%;
the data show that the compound shown in the general formula I with the novel structure shows good activity on various pathogenic bacteria in the agricultural field, and the compound shows outstanding activity effect under certain low dosage, and the activity effect is excellent compared with that of a control compound.
Other compounds of formula I of the present invention, which may also have corresponding activity, are tested accordingly in the manner described above for biological activity.
Claims (8)
1. A substituted isoxazolyl ethylamine compound is characterized in that: the substituted isoxazolyl ethylamine compound is a compound shown in a general formula I;
in the formula:
R 1 selected from hydrogen, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkynyl, C 3 -C 12 Alkenyloxy, halogeno C 3 -C 12 Alkenyloxy radical, C 3 -C 12 Alkynyloxy, halo C 3 -C 12 Alkynyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl or C 1 -C 12 Alkylthio group C 1 -C 12 An alkyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, di (halo C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkylthio, halo C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogeno C 2 -C 12 Alkenyloxy radical, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkylcarbonyl group, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio groupCarbonyl group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylcarbonyloxy, halo C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo C 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo C 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy or halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkenyl, halo C 2 -C 12 Alkynyl, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylsulfinyl, halogeno C 1 -C 12 Alkylsulfinyl radical, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylaminosulfonyl, di (C) 1 -C 12 Alkyl) aminosulfonyl, C 1 -C 12 Alkylsulfonylaminocarbonyl group, C 1 -C 12 Alkylcarbonylaminosulfonyl radical, C 3 -C 12 Cycloalkyloxycarbonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkyl carbonyl, C 1 -C 12 Alkoxycarbonyl, halo C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkyl carbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylaminocarbonyl, di (C) 1 -C 12 Alkyl) aminocarbonyl, C 2 -C 12 Alkenyloxycarbonyl radical, C 2 -C 12 Alkynyloxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxycarbonyl, arylcarbonyl C which is unsubstituted or substituted by 1 to 5 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C 1 -C 6 Alkyloxycarbonyl, aryl C 1 -C 6 Alkyl, heteroaryl carbonyl C 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C 1 -C 6 Alkyloxycarbonyl, heteroaryl C 1 -C 6 Alkyl, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 4 、R 5 C attached thereto may also form C 3 -C 8 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy or halo C 1 -C 12 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 8 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted aryl, heteroaryl;
R 8 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halo C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxy, halo C 1 -C 12 Alkoxy radical, C 3 -C 12 Cycloalkyl radical, C 1 -C 12 Alkylamino, halogeno C 1 -C 12 Alkylamino radical, di (C) 1 -C 12 Alkyl) amino, halo-di (C) 1 -C 12 Alkyl) amino, C 1 -C 12 Alkylthio, halogeno C 1 -C 12 Alkylthio radical, C 2 -C 12 Alkenyl radical, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogeno C 2 -C 12 Alkenyloxy radical, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl radical, C 1 -C 12 Alkylcarbonyl, halo C 1 -C 12 Alkyl carbonyl, C 1 -C 12 Alkoxycarbonyl, halogeno C 1 -C 12 Alkoxycarbonyl group, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxy radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio C 1 -C 12 Alkyl radical, C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl, halo C 1 -C 12 Alkoxycarbonyl radical C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl, halo C 1 -C 12 Alkylthio carbonyl group C 1 -C 12 Alkyl radical, C 1 -C 12 Alkylcarbonyloxy, halo C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo C 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo C 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy radical C 1 -C 12 Alkoxy or halo C 1 -C 12 Alkoxy radical C 1 -C 12 An alkoxy group.
2. A substituted isoxazolylethylamine compound according to claim 1, characterized in that: in the compounds of the general formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl, C 3 -C 6 Alkenyloxy, halogeno C 3 -C 6 Alkenyloxy radical, C 3 -C 6 Alkynyloxy, halo C 3 -C 6 Alkynyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl or C 1 -C 6 Alkylthio group C 1 -C 6 An alkyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, di (halo C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkylthio, halogeno C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogeno C 2 -C 6 Alkenyloxy radical, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halogeno C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylcarbonyloxy, halo C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo C 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo C 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy or halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkynyl, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylsulfinyl, halogeno C 1 -C 6 Alkylsulfinyl radical, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylaminosulfonyl, di (C) 1 -C 6 Alkyl) aminosulfonyl, C 1 -C 6 Alkylsulfonylaminocarbonyl group, C 1 -C 6 Alkylcarbonylaminosulfonyl radical, C 3 -C 6 Cycloalkyloxycarbonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkylcarbonyl group, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkyl carbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylaminocarbonyl, di (C) 1 -C 6 Alkyl) aminocarbonyl, C 2 -C 6 Alkenyloxycarbonyl radical, C 2 -C 6 Alkynyloxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxycarbonyl, arylcarbonyl C which is unsubstituted or substituted by 1 to 5 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, aryl C 1 -C 6 Alkyloxycarbonyl, aryl C 1 -C 6 Alkyl, heteroaryl carbonyl C 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaryl C 1 -C 6 Alkyloxycarbonyl, heteroaryl C 1 -C 6 Alkyl, the following groups being halogen, nitro, cyano, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
R 4 、R 5 are identicalOr different from each other and are independently selected from hydrogen, halogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 4 、R 5 C attached thereto may also form C 3 -C 6 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy or halo C 1 -C 6 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 6 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted aryl, heteroaryl;
R 8 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 3 -C 6 Cycloalkyl radical, C 1 -C 6 Alkylamino, halogeno C 1 -C 6 Alkylamino radical, di (C) 1 -C 6 Alkyl) amino, halo-di (C) 1 -C 6 Alkyl) amino, C 1 -C 6 Alkylthio, halogeno C 1 -C 6 Alkylthio radical, C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogeno C 2 -C 6 Alkenyloxy radical, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylcarbonyl, halo C 1 -C 6 Alkyl carbonyl, C 1 -C 6 Alkoxycarbonyl, halo C 1 -C 6 Alkoxycarbonyl group, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxy radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl, halo C 1 -C 6 Alkoxycarbonyl radical C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl, halo C 1 -C 6 Alkylthio carbonyl group C 1 -C 6 Alkyl radical, C 1 -C 6 Alkylcarbonyloxy, halo C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo C 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo C 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy radical C 1 -C 6 Alkoxy or halo C 1 -C 6 Alkoxy radical C 1 -C 6 An alkoxy group.
3. A substituted isoxazolylethylamine compound according to claim 2, characterized in that: in the compounds of the general formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 An alkynyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino,Bis (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkyl carbonyl, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halogeno C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 An alkoxycarbonyl group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 C connected thereto may also form C 3 -C 4 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 C attached thereto may also form C 3 -C 4 A ring of (a);
q is selected from unsubstituted or substituted by 1-5R 8 Substituted phenyl, pyridyl, thienyl, furyl, pyrazolyl, thiazolyl, isothiazolyl, pyrazine, pyridazine;
R 8 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halogeno C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 An alkoxy group.
4. A substituted isoxazolylethylamine compound according to claim 3, characterized in that: in the compounds of the general formula I:
R 1 selected from hydrogen, C 1 -C 6 Alkyl, halo C 1 -C 6 Alkyl radical, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkoxy, halo C 1 -C 6 Alkoxy radical, C 2 -C 6 Alkenyl, halo C 2 -C 6 Alkenyl radical, C 2 -C 6 Alkynyl, halo C 2 -C 6 An alkynyl group;
R 2 selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, di (halo C) 1 -C 4 Alkyl) amino, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogeno C 2 -C 4 Alkenyloxy radical, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkyl carbonyl, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 Alkoxycarbonyl group, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxycarbonyl radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio carbonyl group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylcarbonyloxy, halo C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo C 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo C 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy or halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkoxy radical, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from hydrogen, hydroxy, formyl, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical, C 3 -C 4 Cycloalkyl radical, C 2 -C 4 Alkenyl radical, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halo C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl, halo C 1 -C 4 Alkoxy radical C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl, halo C 1 -C 4 Alkylthio group C 1 -C 4 Alkyl radical, C 1 -C 4 Alkylsulfinyl, halogeno C 1 -C 4 Alkylsulfinyl radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl radical, C 1 -C 4 Alkylaminosulfonyl, di (C) 1 -C 4 Alkyl) aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl group, C 1 -C 4 Alkylcarbonylaminosulfonyl radical, C 3 -C 4 Cycloalkyloxycarbonyl radical, C 1 -C 4 Alkylcarbonyl, halo C 1 -C 4 Alkylcarbonyl group, C 1 -C 4 Alkoxycarbonyl, halo C 1 -C 4 An alkoxycarbonyl group;
R 4 、R 5 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 4 、R 5 C attached thereto may also form C 3 -C 4 A ring of (a);
R 6 、R 7 same or different are respectively selected from hydrogen, halogen and C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy or halo C 1 -C 4 An alkoxy group;
wherein R is 6 、R 7 C connected thereto may also form C 3 -C 4 A ring of (a);
q is selected from the following substituents:
R 8 selected from halogen, amino, cyano, nitro, C 1 -C 4 Alkyl, halo C 1 -C 4 Alkyl radical, C 1 -C 4 Alkoxy, halo C 1 -C 4 Alkoxy radical,C 3 -C 4 Cycloalkyl radical, C 1 -C 4 Alkylamino, halogeno C 1 -C 4 Alkylamino radical, di (C) 1 -C 4 Alkyl) amino, halo-di (C) 1 -C 4 Alkyl) amino, aminocarbonyl, di-C 1 -C 4 Alkylaminocarbonyl, dihalo-C 1 -C 4 Alkylaminocarbonyl radical, C 1 -C 4 Alkylthio, halo C 1 -C 4 Alkylthio radical, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 An alkylsulfonyl group;
m is selected from an integer of 0 to 5, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
5. A substituted isoxazolylethylamine compound according to claim 4, characterized in that: in the compounds of formula I:
R 1 selected from hydrogen, cyano, fluoro, chloro, bromo, iodo, methyl, ethyl or trifluoromethyl;
R 2 selected from the group consisting of fluoro, chloro, bromo, iodo, hydroxy, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano or hydroxyl;
n is an integer from 0 to 5, and when n is 0, no substituent is present; when n is greater than 1, R 2 The same or different;
R 3 selected from the group consisting of hydrogen, hydroxy, formyl, acetyl, propionyl, butyryl, trifluoroacetyl, benzoyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoroethoxy, cyclopropyloxy, allyl, propargyl, methanesulfonateAcyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethyleneoxycarbonyl, acetylenyloxycarbonyl;
R 4 、R 5 identical or different are each selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
R 6 、R 7 identical or different from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;
q is selected from the following substituents:
R 8 selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl;
m is selected from an integer of 0 to 5, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
6. A substituted isoxazolylethylamine compound according to claim 5, characterized in that: in the compounds of formula I:
R 1 selected from hydrogen or methyl;
R 3 selected from hydrogen;
R 2 selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, R 2 When the position is 4 of the benzene ring, the compound is not selected from cyano;
R 4 、R 5 the same or different is selected from hydrogen, fluorine, chlorine, bromine or methyl;
R 6 、R 7 are all selected from hydrogen;
n is an integer of 0 to 5, and when n is 0, no substituent is on the ring; when n is greater than 1, R 2 The same or different;
q is selected from the following substituents:
R 8 selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy;
m is selected from an integer of 0 to 4, and when m is 0, no substituent is present; when m is greater than 1, R 8 The same or different.
7. A process for the preparation of substituted isoxazolylethylamines according to claim 1, characterized in that:
the preparation method of the compound shown in the general formula I comprises the following steps:
8. use of a substituted isoxazolylethylamine compound according to claim 1, for the preparation of a bactericidal pharmaceutical formulation.
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